data_1
 
_audit_creation_date                    2009-05-29T12:41:15-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C6 H7 I N, Cl'
_chemical_formula_sum                   'C6 H7 Cl I N'
_chemical_formula_weight                255.48
_chemical_compound_source               'synthesis as described'
_chemical_absolute_configuration        unk
 
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting                  orthorhombic
_symmetry_space_group_name_H-M          'P 21 a b'
_symmetry_space_group_name_Hall         'P -2b 2a'
 
loop_
    _symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, -z'
'x+1/2, -y+1/2, z'
'x, y+1/2, -z'
 
_cell_length_a                          8.2800(3)
_cell_length_b                          9.8354(5)
_cell_length_c                          10.7554(4)
_cell_angle_alpha                       90
_cell_angle_beta                        90
_cell_angle_gamma                       90
_cell_volume                            875.89(6)
_cell_formula_units_Z                   4
_cell_measurement_temperature           123(2)
_cell_measurement_reflns_used           4425
_cell_measurement_theta_min             0.407
_cell_measurement_theta_max             28.283
_cell_measurement_wavelength            0.71073
 
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
 
_exptl_crystal_description              block
_exptl_crystal_colour                   colorless
_exptl_crystal_size_max                 0.25
_exptl_crystal_size_mid                 0.20
_exptl_crystal_size_min                 0.15
_exptl_crystal_density_diffrn           1.937
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    480
_exptl_special_details
;
 ?
;
 
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
 
_exptl_absorpt_coefficient_mu           3.882
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details         '(Blessing et al., 1995)'
_exptl_absorpt_correction_T_max         0.7456
_exptl_absorpt_correction_T_min         0.5169

 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
 
_diffrn_source                          'Enraf Nonius FR590'
_diffrn_ambient_temperature             123(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_radiation_probe                 x-ray
_diffrn_detector                        'CCD plate'
_diffrn_detector_area_resol_mean        9
_diffrn_orient_matrix_type
                                     'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11             -0.117708
_diffrn_orient_matrix_ub_12             -0.204881E-1
_diffrn_orient_matrix_ub_13             0.89984E-2
_diffrn_orient_matrix_ub_21             -0.119095E-1
_diffrn_orient_matrix_ub_22             -0.291E-4
_diffrn_orient_matrix_ub_23             -0.925215E-1
_diffrn_orient_matrix_ub_31             0.242696E-1
_diffrn_orient_matrix_ub_32             -0.995879E-1
_diffrn_orient_matrix_ub_33             -0.18553E-2
_diffrn_measurement_device              '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type         KappaCCD
_diffrn_measurement_method              'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents         0.0301
_diffrn_reflns_av_unetI/netI            0.0267
_diffrn_reflns_number                   9794
_diffrn_reflns_limit_h_min              -10
_diffrn_reflns_limit_h_max              9
_diffrn_reflns_limit_k_min              -9
_diffrn_reflns_limit_k_max              12
_diffrn_reflns_limit_l_min              -13
_diffrn_reflns_limit_l_max              13
_diffrn_reflns_theta_min                2.81
_diffrn_reflns_theta_max                27.49
_diffrn_reflns_theta_full               27.49
_diffrn_measured_fraction_theta_full
                                        0.987
_diffrn_measured_fraction_theta_max
                                        0.987
_reflns_number_total                    1900
_reflns_number_gt                       1800
_reflns_threshold_expression            >2σ(I)
 
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
 
_computing_data_collection              'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement
                                       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
                             'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution           'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
                                   'WinGX publication routines (Farrugia, 1999)'
 
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
 
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
 
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0000P)²+0.4332P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment           constr
_refine_ls_extinction_method            none
_refine_ls_number_reflns                1900
_refine_ls_number_parameters            83
_refine_ls_number_restraints            1
_refine_ls_R_factor_all                 0.0209
_refine_ls_R_factor_gt                  0.0182
_refine_ls_wR_factor_ref                0.0335
_refine_ls_wR_factor_gt                 0.0328
_refine_ls_goodness_of_fit_ref          1.045
_refine_ls_restrained_S_all             1.045
_refine_ls_shift/su_max                 0.002
_refine_ls_shift/su_mean                0
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack          0.06(2)
_refine_diff_density_max                0.308
_refine_diff_density_min                -0.405
_refine_diff_density_rms                0.075
 
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
 
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
loop_
    _atom_site_label
    _atom_site_type_symbol
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_disorder_assembly
    _atom_site_disorder_group
I1 I 0.46378(4) 0.882441(14) 0.337552(13) 0.02702(6) Uani 1 1 d . . .
C2 C 0.5226(3) 0.8869(3) 0.5276(3) 0.0222(6) Uani 1 1 d . . .
C3 C 0.4589(5) 0.9897(2) 0.6030(2) 0.0244(5) Uani 1 1 d . . .
H3 H 0.391 1.0577 0.5683 0.029 Uiso 1 1 calc R . .
C4 C 0.4955(3) 0.9914(3) 0.7280(3) 0.0250(7) Uani 1 1 d . . .
H4 H 0.4528 1.0605 0.7802 0.03 Uiso 1 1 calc R . .
C5 C 0.5947(3) 0.8920(3) 0.7767(3) 0.0225(6) Uani 1 1 d . . .
C6 C 0.6571(4) 0.7897(3) 0.7040(3) 0.0272(6) Uani 1 1 d . . .
H6 H 0.7241 0.7216 0.7395 0.033 Uiso 1 1 calc R . .
C7 C 0.6210(4) 0.7873(3) 0.5779(3) 0.0259(6) Uani 1 1 d . . .
H7 H 0.6636 0.7175 0.5264 0.031 Uiso 1 1 calc R . .
N8 N 0.6332(3) 0.8976(2) 0.9101(2) 0.0261(5) Uani 1 1 d . . .
H8A H 0.682 0.9782 0.9278 0.039 Uiso 1 1 calc R . .
H8B H 0.7009 0.828 0.9298 0.039 Uiso 1 1 calc R . .
H8C H 0.5406 0.89 0.9551 0.039 Uiso 1 1 calc R . .
Cl9 Cl 0.31819(9) 0.83381(8) 0.04486(6) 0.03029(15) Uani 1 1 d . . .
 
 
 
#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_distance
    _geom_bond_site_symmetry_2
    _geom_bond_publ_flag
I1 C2 2.101(3) . ?
C2 C7 1.384(4) . ?
C2 C3 1.399(4) . ?
C3 C4 1.378(3) . ?
C3 H3 0.95 . ?
C4 C5 1.380(4) . ?
C4 H4 0.95 . ?
C5 C6 1.375(4) . ?
C5 N8 1.471(4) . ?
C6 C7 1.389(4) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
N8 H8A 0.91 . ?
N8 H8B 0.91 . ?
N8 H8C 0.91 . ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C7 C2 C3 120.4(3) . . ?
C7 C2 I1 120.1(2) . . ?
C3 C2 I1 119.4(2) . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 121.8(3) . . ?
C6 C5 N8 120.0(2) . . ?
C4 C5 N8 118.2(2) . . ?
C5 C6 C7 119.1(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C6 119.8(3) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C5 N8 H8A 109.5 . . ?
C5 N8 H8B 109.5 . . ?
H8A N8 H8B 109.5 . . ?
C5 N8 H8C 109.5 . . ?
H8A N8 H8C 109.5 . . ?
H8B N8 H8C 109.5 . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C7 C2 C3 C4 0.3(5) . . . . ?
I1 C2 C3 C4 179.0(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C3 C4 C5 N8 179.2(2) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
N8 C5 C6 C7 -179.2(3) . . . . ?
C3 C2 C7 C6 -0.2(4) . . . . ?
I1 C2 C7 C6 -179.0(2) . . . . ?
C5 C6 C7 C2 -0.3(4) . . . . ?


data_5
 
_audit_creation_date                    2009-07-01T16:07:33-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C6 H7 I N, Br'
_chemical_formula_sum                   'C6 H7 Br I N'
_chemical_formula_weight                299.93
_chemical_compound_source               'synthesis as described'
 
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting                  triclinic
_symmetry_space_group_name_H-M          'P -1'
_symmetry_space_group_name_Hall         '-P 1'
_symmetry_Int_Tables_number             2
 
loop_
    _symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
 
_cell_length_a                          10.0650(4)
_cell_length_b                          10.9183(3)
_cell_length_c                          12.6269(4)
_cell_angle_alpha                       100.866(2)
_cell_angle_beta                        106.743(2)
_cell_angle_gamma                       95.177(2)
_cell_volume                            1289.45(7)
_cell_formula_units_Z                   6
_cell_measurement_temperature           123(2)
_cell_measurement_reflns_used           5235
_cell_measurement_theta_min             0.407
_cell_measurement_theta_max             28.283
_cell_measurement_wavelength            0.71073
 
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
 
_exptl_crystal_description              prism
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.4
_exptl_crystal_size_mid                 0.09
_exptl_crystal_size_min                 0.09
_exptl_crystal_density_diffrn           2.318
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    828
_exptl_special_details
;
 ?
;
 
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
 
_exptl_absorpt_coefficient_mu           8.293
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min         0.2072
_exptl_absorpt_correction_T_max         0.4308

 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
 
_diffrn_source                          'Enraf Nonius FR590'
_diffrn_ambient_temperature             123(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_radiation_probe                 x-ray
_diffrn_detector                        'CCD plate'
_diffrn_detector_area_resol_mean        9
_diffrn_orient_matrix_type
                                     'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11             -0.639226E-1
_diffrn_orient_matrix_ub_12             -0.679093E-1
_diffrn_orient_matrix_ub_13             -0.635711E-1
_diffrn_orient_matrix_ub_21             -0.645832E-1
_diffrn_orient_matrix_ub_22             0.616865E-1
_diffrn_orient_matrix_ub_23             -0.222128E-1
_diffrn_orient_matrix_ub_31             0.526113E-1
_diffrn_orient_matrix_ub_32             0.22163E-1
_diffrn_orient_matrix_ub_33             -0.51666E-1
_diffrn_measurement_device              '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type         KappaCCD
_diffrn_measurement_method              'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents         0.0547
_diffrn_reflns_av_unetI/netI            0.0604
_diffrn_reflns_number                   14366
_diffrn_reflns_limit_h_min              -11
_diffrn_reflns_limit_h_max              10
_diffrn_reflns_limit_k_min              -12
_diffrn_reflns_limit_k_max              12
_diffrn_reflns_limit_l_min              -12
_diffrn_reflns_limit_l_max              14
_diffrn_reflns_theta_min                2.86
_diffrn_reflns_theta_max                25
_diffrn_reflns_theta_full               25
_diffrn_measured_fraction_theta_full
                                        0.972
_diffrn_measured_fraction_theta_max
                                        0.972
_reflns_number_total                    4404
_reflns_number_gt                       3599
_reflns_threshold_expression            >2σ(I)
 
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
 
_computing_data_collection              'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement
                                       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
                             'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution           'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
                                   'WinGX publication routines (Farrugia, 1999)'
 
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
 
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
 
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
        'calc w=1/[σ²(Fo²)+(0.0503P)²+18.0563P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment           constr
_refine_ls_extinction_method            none
_refine_ls_number_reflns                4404
_refine_ls_number_parameters            250
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.0688
_refine_ls_R_factor_gt                  0.0543
_refine_ls_wR_factor_ref                0.1374
_refine_ls_wR_factor_gt                 0.1295
_refine_ls_goodness_of_fit_ref          1.058
_refine_ls_restrained_S_all             1.058
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                2.211
_refine_diff_density_min                -1.236
_refine_diff_density_rms                0.218
 
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
 
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
loop_
    _atom_site_label
    _atom_site_type_symbol
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_disorder_assembly
    _atom_site_disorder_group
I1 I 0.58863(7) 0.32900(7) 0.78441(6) 0.0368(2) Uani 1 1 d . . .
C2 C 0.6126(10) 0.5269(9) 0.8305(8) 0.025(2) Uani 1 1 d . . .
C3 C 0.7082(11) 0.5975(10) 0.7981(9) 0.031(2) Uani 1 1 d . . .
H3 H 0.763 0.5561 0.7567 0.038 Uiso 1 1 calc R . .
C4 C 0.7254(11) 0.7291(10) 0.8254(8) 0.032(2) Uani 1 1 d . . .
H4 H 0.7887 0.7785 0.8013 0.038 Uiso 1 1 calc R . .
C5 C 0.6465(10) 0.7850(9) 0.8893(8) 0.024(2) Uani 1 1 d . . .
N6 N 0.6585(10) 0.9238(8) 0.9164(7) 0.033(2) Uani 1 1 d . . .
H6A H 0.5872 0.9479 0.8657 0.049 Uiso 1 1 calc R . .
H6B H 0.7422 0.9584 0.9127 0.049 Uiso 1 1 calc R . .
H6C H 0.6535 0.9506 0.9877 0.049 Uiso 1 1 calc R . .
C7 C 0.5516(11) 0.7166(10) 0.9231(8) 0.029(2) Uani 1 1 d . . .
H7 H 0.4981 0.7581 0.9656 0.034 Uiso 1 1 calc R . .
C8 C 0.5348(10) 0.5863(10) 0.8945(9) 0.030(2) Uani 1 1 d . . .
H8 H 0.4706 0.5375 0.9183 0.036 Uiso 1 1 calc R . .
I9 I 0.20991(8) 0.30155(6) 0.46912(6) 0.0337(2) Uani 1 1 d . . .
C10 C 0.2453(10) 0.4980(9) 0.4969(8) 0.023(2) Uani 1 1 d . . .
C11 C 0.3780(10) 0.5656(9) 0.5623(8) 0.026(2) Uani 1 1 d . . .
H11 H 0.4521 0.5225 0.5943 0.031 Uiso 1 1 calc R . .
C12 C 0.4001(10) 0.6956(9) 0.5796(8) 0.025(2) Uani 1 1 d . . .
H12 H 0.4895 0.7423 0.624 0.03 Uiso 1 1 calc R . .
C13 C 0.2932(10) 0.7569(9) 0.5329(7) 0.022(2) Uani 1 1 d . . .
N14 N 0.3185(9) 0.8949(7) 0.5498(7) 0.0305(19) Uani 1 1 d . . .
H14A H 0.2448 0.9278 0.5658 0.046 Uiso 1 1 calc R . .
H14B H 0.328 0.9154 0.4855 0.046 Uiso 1 1 calc R . .
H14C H 0.3985 0.9271 0.6085 0.046 Uiso 1 1 calc R . .
C15 C 0.1628(11) 0.6925(10) 0.4705(9) 0.031(2) Uani 1 1 d . . .
H15 H 0.0893 0.7365 0.4391 0.037 Uiso 1 1 calc R . .
C16 C 0.1391(10) 0.5628(9) 0.4533(8) 0.024(2) Uani 1 1 d . . .
H16 H 0.0482 0.5177 0.4109 0.029 Uiso 1 1 calc R . .
I17 I 0.85575(9) 0.33001(7) 0.15494(7) 0.0496(3) Uani 1 1 d . . .
C18 C 0.8896(10) 0.5249(10) 0.1728(9) 0.030(2) Uani 1 1 d . . .
C19 C 0.9937(12) 0.5803(11) 0.1373(9) 0.038(3) Uani 1 1 d . . .
H19 H 1.0469 0.5291 0.1015 0.045 Uiso 1 1 calc R . .
C20 C 1.0201(11) 0.7107(11) 0.1542(8) 0.031(2) Uani 1 1 d . . .
H20 H 1.0911 0.7492 0.13 0.038 Uiso 1 1 calc R . .
C21 C 0.9430(11) 0.7832(10) 0.2060(9) 0.031(2) Uani 1 1 d . . .
N22 N 0.9736(10) 0.9222(8) 0.2275(7) 0.036(2) Uani 1 1 d . . .
H22A H 1.0291 0.9535 0.3005 0.053 Uiso 1 1 calc R . .
H22B H 0.8918 0.9547 0.2159 0.053 Uiso 1 1 calc R . .
H22C H 1.0188 0.9441 0.1794 0.053 Uiso 1 1 calc R . .
C23 C 0.8390(10) 0.7299(10) 0.2417(8) 0.027(2) Uani 1 1 d . . .
H23 H 0.7859 0.7817 0.2772 0.033 Uiso 1 1 calc R . .
C24 C 0.8124(10) 0.5984(10) 0.2250(9) 0.029(2) Uani 1 1 d . . .
H24 H 0.7414 0.5603 0.2496 0.035 Uiso 1 1 calc R . .
Br1A Br 1 1 0.5 0.0248(3) Uani 1 2 d S . .
Br1B Br 1 1 0 0.0383(4) Uani 1 2 d S . .
Br2 Br 0.66902(10) 0.01303(9) 0.67911(8) 0.0252(2) Uani 1 1 d . . .
Br3 Br 0.66618(11) 0.02043(10) 0.17868(8) 0.0327(3) Uani 1 1 d . . .
 
 
 
#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_distance
    _geom_bond_site_symmetry_2
    _geom_bond_publ_flag
I1 C2 2.102(10) . ?
C2 C3 1.379(15) . ?
C2 C8 1.394(14) . ?
C3 C4 1.396(15) . ?
C3 H3 0.95 . ?
C4 C5 1.387(14) . ?
C4 H4 0.95 . ?
C5 C7 1.371(14) . ?
C5 N6 1.475(13) . ?
N6 H6A 0.91 . ?
N6 H6B 0.91 . ?
N6 H6C 0.91 . ?
C7 C8 1.382(15) . ?
C7 H7 0.95 . ?
C8 H8 0.95 . ?
I9 C10 2.087(9) . ?
C10 C16 1.375(13) . ?
C10 C11 1.403(14) . ?
C11 C12 1.382(14) . ?
C11 H11 0.95 . ?
C12 C13 1.366(13) . ?
C12 H12 0.95 . ?
C13 C15 1.366(14) . ?
C13 N14 1.469(12) . ?
N14 H14A 0.91 . ?
N14 H14B 0.91 . ?
N14 H14C 0.91 . ?
C15 C16 1.379(14) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
I17 C18 2.083(10) . ?
C18 C24 1.375(14) . ?
C18 C19 1.387(16) . ?
C19 C20 1.388(16) . ?
C19 H19 0.95 . ?
C20 C21 1.365(15) . ?
C20 H20 0.95 . ?
C21 C23 1.378(14) . ?
C21 N22 1.479(14) . ?
N22 H22A 0.91 . ?
N22 H22B 0.91 . ?
N22 H22C 0.91 . ?
C23 C24 1.400(15) . ?
C23 H23 0.95 . ?
C24 H24 0.95 . ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C3 C2 C8 120.3(9) . . ?
C3 C2 I1 119.0(7) . . ?
C8 C2 I1 120.7(8) . . ?
C2 C3 C4 120.6(10) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 117.5(10) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
C7 C5 C4 122.8(10) . . ?
C7 C5 N6 118.2(9) . . ?
C4 C5 N6 118.9(9) . . ?
C5 N6 H6A 109.5 . . ?
C5 N6 H6B 109.5 . . ?
H6A N6 H6B 109.5 . . ?
C5 N6 H6C 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
C5 C7 C8 119.0(10) . . ?
C5 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C7 C8 C2 119.7(10) . . ?
C7 C8 H8 120.1 . . ?
C2 C8 H8 120.1 . . ?
C16 C10 C11 119.2(9) . . ?
C16 C10 I9 120.8(7) . . ?
C11 C10 I9 120.0(7) . . ?
C12 C11 C10 119.4(9) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 120.0(9) . . ?
C13 C12 H12 120 . . ?
C11 C12 H12 120 . . ?
C12 C13 C15 121.3(9) . . ?
C12 C13 N14 119.5(8) . . ?
C15 C13 N14 119.2(9) . . ?
C13 N14 H14A 109.5 . . ?
C13 N14 H14B 109.5 . . ?
H14A N14 H14B 109.5 . . ?
C13 N14 H14C 109.5 . . ?
H14A N14 H14C 109.5 . . ?
H14B N14 H14C 109.5 . . ?
C13 C15 C16 119.3(9) . . ?
C13 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C10 C16 C15 120.8(9) . . ?
C10 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C24 C18 C19 120.3(10) . . ?
C24 C18 I17 119.4(8) . . ?
C19 C18 I17 120.2(8) . . ?
C18 C19 C20 119.9(10) . . ?
C18 C19 H19 120 . . ?
C20 C19 H19 120 . . ?
C21 C20 C19 119.4(10) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C23 121.5(10) . . ?
C20 C21 N22 119.7(10) . . ?
C23 C21 N22 118.8(10) . . ?
C21 N22 H22A 109.5 . . ?
C21 N22 H22B 109.5 . . ?
H22A N22 H22B 109.5 . . ?
C21 N22 H22C 109.5 . . ?
H22A N22 H22C 109.5 . . ?
H22B N22 H22C 109.5 . . ?
C21 C23 C24 119.2(10) . . ?
C21 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C18 C24 C23 119.6(10) . . ?
C18 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C8 C2 C3 C4 -2.1(15) . . . . ?
I1 C2 C3 C4 178.9(7) . . . . ?
C2 C3 C4 C5 2.2(14) . . . . ?
C3 C4 C5 C7 -1.7(14) . . . . ?
C3 C4 C5 N6 -178.0(9) . . . . ?
C4 C5 C7 C8 1.2(14) . . . . ?
N6 C5 C7 C8 177.4(9) . . . . ?
C5 C7 C8 C2 -1.0(14) . . . . ?
C3 C2 C8 C7 1.5(15) . . . . ?
I1 C2 C8 C7 -179.5(7) . . . . ?
C16 C10 C11 C12 -1.3(14) . . . . ?
I9 C10 C11 C12 179.8(7) . . . . ?
C10 C11 C12 C13 -0.2(14) . . . . ?
C11 C12 C13 C15 1.2(14) . . . . ?
C11 C12 C13 N14 -178.7(9) . . . . ?
C12 C13 C15 C16 -0.6(15) . . . . ?
N14 C13 C15 C16 179.3(9) . . . . ?
C11 C10 C16 C15 1.8(14) . . . . ?
I9 C10 C16 C15 -179.2(7) . . . . ?
C13 C15 C16 C10 -0.9(15) . . . . ?
C24 C18 C19 C20 -0.2(15) . . . . ?
I17 C18 C19 C20 -177.0(8) . . . . ?
C18 C19 C20 C21 0.1(15) . . . . ?
C19 C20 C21 C23 -0.2(15) . . . . ?
C19 C20 C21 N22 178.1(9) . . . . ?
C20 C21 C23 C24 0.4(15) . . . . ?
N22 C21 C23 C24 -177.9(9) . . . . ?
C19 C18 C24 C23 0.3(15) . . . . ?
I17 C18 C24 C23 177.2(7) . . . . ?
C21 C23 C24 C18 -0.4(14) . . . . ?


data_6
 
_audit_creation_date                    2009-09-23T15:14:24-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C6 H7 I N, H2 O4 P'
_chemical_formula_sum                   'C6 H9 I N O4 P'
_chemical_formula_weight                317.01
_chemical_compound_source               'synthesis as described'
 
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting                  orthorhombic
_symmetry_space_group_name_H-M          'P c a b'
_symmetry_space_group_name_Hall         '-P 2bc 2ac'
 
loop_
    _symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x-1/2, -y-1/2, z'
 
_cell_length_a                          7.81190(10)
_cell_length_b                          9.8242(2)
_cell_length_c                          25.8681(5)
_cell_angle_alpha                       90
_cell_angle_beta                        90
_cell_angle_gamma                       90
_cell_volume                            1985.26(6)
_cell_formula_units_Z                   8
_cell_measurement_temperature           123(2)
_cell_measurement_reflns_used           40034
_cell_measurement_theta_min             1
_cell_measurement_theta_max             25
_cell_measurement_wavelength            0.71073
 
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
 
_exptl_crystal_description              block
_exptl_crystal_colour                   colorless
_exptl_crystal_size_max                 0.4
_exptl_crystal_size_mid                 0.35
_exptl_crystal_size_min                 0.25
_exptl_crystal_density_diffrn           2.121
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    1216
_exptl_special_details
;
 ?
;
 
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
 
_exptl_absorpt_coefficient_mu           3.371
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details         '(Blessing et al., 1995)'
_exptl_absorpt_correction_T_max         0.4302
_exptl_absorpt_correction_T_min         0.2749
 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
 
_diffrn_source                          'Enraf Nonius FR590'
_diffrn_ambient_temperature             123(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_radiation_probe                 x-ray
_diffrn_detector                        'CCD plate'
_diffrn_detector_area_resol_mean        9
_diffrn_orient_matrix_type
                                     'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11             -0.908266E-1
_diffrn_orient_matrix_ub_12             -0.714702E-1
_diffrn_orient_matrix_ub_13             -0.23104E-2
_diffrn_orient_matrix_ub_21             0.631604E-1
_diffrn_orient_matrix_ub_22             -0.565504E-1
_diffrn_orient_matrix_ub_23             0.258719E-1
_diffrn_orient_matrix_ub_31             -0.644034E-1
_diffrn_orient_matrix_ub_32             0.453338E-1
_diffrn_orient_matrix_ub_33             0.286308E-1
_diffrn_measurement_device              '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type         KappaCCD
_diffrn_measurement_method              'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents         0.0353
_diffrn_reflns_av_unetI/netI            0.0203
_diffrn_reflns_number                   24333
_diffrn_reflns_limit_h_min              -10
_diffrn_reflns_limit_h_max              10
_diffrn_reflns_limit_k_min              -12
_diffrn_reflns_limit_k_max              12
_diffrn_reflns_limit_l_min              -33
_diffrn_reflns_limit_l_max              33
_diffrn_reflns_theta_min                2.6
_diffrn_reflns_theta_max                27.5
_diffrn_reflns_theta_full               27.5
_diffrn_measured_fraction_theta_full
                                        0.998
_diffrn_measured_fraction_theta_max
                                        0.998
_reflns_number_total                    2271
_reflns_number_gt                       2140
_reflns_threshold_expression            >2σ(I)
 
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
 
_computing_data_collection              'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement
                                       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
                             'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution           'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
                                   'WinGX publication routines (Farrugia, 1999)'
 
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
 
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
 
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0120P)²+3.9613P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment           constr
_refine_ls_extinction_method            none
_refine_ls_number_reflns                2271
_refine_ls_number_parameters            121
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.025
_refine_ls_R_factor_gt                  0.0228
_refine_ls_wR_factor_ref                0.0509
_refine_ls_wR_factor_gt                 0.0499
_refine_ls_goodness_of_fit_ref          1.151
_refine_ls_restrained_S_all             1.151
_refine_ls_shift/su_max                 0.002
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.486
_refine_diff_density_min                -0.534
_refine_diff_density_rms                0.092
 
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
 
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
loop_
    _atom_site_label
    _atom_site_type_symbol
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_disorder_assembly
    _atom_site_disorder_group
I1 I 0.60899(2) 0.380046(17) 0.814120(6) 0.02111(6) Uani 1 1 d . . .
C2 C 0.5725(3) 0.3798(2) 0.73355(9) 0.0167(5) Uani 1 1 d . . .
C3 C 0.6373(3) 0.4860(2) 0.70400(10) 0.0177(5) Uani 1 1 d . . .
H3 H 0.6941 0.5601 0.7202 0.021 Uiso 1 1 calc R . .
C4 C 0.6185(3) 0.4832(2) 0.65059(10) 0.0175(5) Uani 1 1 d . . .
H4 H 0.6608 0.5559 0.63 0.021 Uiso 1 1 calc R . .
C5 C 0.5369(3) 0.3728(2) 0.62759(9) 0.0132(4) Uani 1 1 d . . .
C6 C 0.4721(3) 0.2669(2) 0.65707(9) 0.0169(5) Uani 1 1 d . . .
H6 H 0.4161 0.1924 0.6409 0.02 Uiso 1 1 calc R . .
C7 C 0.4895(3) 0.2704(3) 0.71061(10) 0.0190(5) Uani 1 1 d . . .
H7 H 0.445 0.1987 0.7312 0.023 Uiso 1 1 calc R . .
N8 N 0.5251(3) 0.36921(19) 0.57123(8) 0.0139(4) Uani 1 1 d . . .
H8A H 0.4619 0.2959 0.5614 0.021 Uiso 1 1 calc R . .
H8B H 0.6321 0.3627 0.5575 0.021 Uiso 1 1 calc R . .
H8C H 0.4741 0.4468 0.5597 0.021 Uiso 1 1 calc R . .
P9 P 0.20274(8) 0.61737(6) 0.53281(2) 0.01344(13) Uani 1 1 d . . .
O10 O 0.1456(2) 0.63602(16) 0.47703(6) 0.0142(3) Uani 1 1 d . . .
O11 O 0.1344(3) 0.4790(2) 0.55507(8) 0.0323(5) Uani 1 1 d . . .
H11 H 0.0343 0.4655 0.5444 0.048 Uiso 1 1 calc R . .
O12 O 0.1345(3) 0.7340(2) 0.56775(8) 0.0352(5) Uani 1 1 d . . .
H12 H 0.0502 0.7713 0.5534 0.053 Uiso 1 1 calc R . .
O13 O 0.3939(2) 0.61011(16) 0.53944(7) 0.0156(3) Uani 1 1 d . . .
 
 
 
#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_distance
    _geom_bond_site_symmetry_2
    _geom_bond_publ_flag
I1 C2 2.104(2) . ?
I1 O12 3.261(2) 3_566 ?
C2 C7 1.388(3) . ?
C2 C3 1.389(3) . ?
C3 C4 1.390(3) . ?
C3 H3 0.95 . ?
C4 C5 1.392(3) . ?
C4 H4 0.95 . ?
C5 C6 1.386(3) . ?
C5 N8 1.461(3) . ?
C6 C7 1.392(3) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
N8 H8A 0.91 . ?
N8 H8B 0.91 . ?
N8 H8C 0.91 . ?
P9 O13 1.5045(17) . ?
P9 O10 1.5214(17) . ?
P9 O12 1.553(2) . ?
P9 O11 1.570(2) . ?
O11 H11 0.84 . ?
O12 H12 0.84 . ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C2 I1 O12 159.46(8) . 3_566 ?
C7 C2 C3 121.1(2) . . ?
C7 C2 I1 119.19(18) . . ?
C3 C2 I1 119.67(18) . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 N8 120.5(2) . . ?
C4 C5 N8 118.3(2) . . ?
C5 C6 C7 119.5(2) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C2 C7 C6 119.4(2) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C5 N8 H8A 109.5 . . ?
C5 N8 H8B 109.5 . . ?
H8A N8 H8B 109.5 . . ?
C5 N8 H8C 109.5 . . ?
H8A N8 H8C 109.5 . . ?
H8B N8 H8C 109.5 . . ?
O13 P9 O10 113.88(10) . . ?
O13 P9 O12 108.00(11) . . ?
O10 P9 O12 111.24(10) . . ?
O13 P9 O11 104.76(10) . . ?
O10 P9 O11 110.63(10) . . ?
O12 P9 O11 107.98(14) . . ?
P9 O11 H11 109.5 . . ?
P9 O12 H12 109.5 . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
O12 I1 C2 C7 16.8(4) 3_566 . . . ?
O12 I1 C2 C3 -160.80(18) 3_566 . . . ?
C7 C2 C3 C4 0.2(4) . . . . ?
I1 C2 C3 C4 177.69(18) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C3 C4 C5 N8 -177.4(2) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
N8 C5 C6 C7 178.0(2) . . . . ?
C3 C2 C7 C6 0.4(4) . . . . ?
I1 C2 C7 C6 -177.07(18) . . . . ?
C5 C6 C7 C2 -0.4(4) . . . . ?
 
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_site_symmetry_A
N8 H8A O10 0.91 2.04 2.930(3) 165.9 4_546
N8 H8B O10 0.91 1.95 2.860(3) 173.9 5_666
N8 H8C O13 0.91 1.8 2.707(2) 173.7 .
O11 H11 O10 0.84 1.81 2.598(3) 155.6 5_566
O12 H12 O13 0.84 1.73 2.533(2) 160.3 8_575



data_8
 
_audit_creation_date                    2009-09-17T11:59:24-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C6 H7 Cl N, H2 O4 P'
_chemical_formula_sum                   'C6 H9 Cl N O4 P'
_chemical_formula_weight                225.56
_chemical_compound_source               'synthesis as described'
 
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting                  orthorhombic
_symmetry_space_group_name_H-M          'P c a b'
_symmetry_space_group_name_Hall         '-P 2bc 2ac'
_symmetry_Int_Tables_number             61
 
loop_
    _symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x-1/2, -y-1/2, z'
 
_cell_length_a                          7.8654(2)
_cell_length_b                          9.6441(3)
_cell_length_c                          25.0515(4)
_cell_angle_alpha                       90
_cell_angle_beta                        90
_cell_angle_gamma                       90
_cell_volume                            1900.27(8)
_cell_formula_units_Z                   8
_cell_measurement_temperature           123(2)
_cell_measurement_reflns_used           2640
_cell_measurement_theta_min             0.407
_cell_measurement_theta_max             28.283
_cell_measurement_wavelength            0.71073
 
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
 
_exptl_crystal_description              block
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.25
_exptl_crystal_size_mid                 0.2
_exptl_crystal_size_min                 0.2
_exptl_crystal_density_diffrn           1.577
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    928
_exptl_special_details
;
 ?
;
 
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
 
_exptl_absorpt_coefficient_mu           0.552
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min         0.6587
_exptl_absorpt_correction_T_max         0.7457
 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
 
_diffrn_source                          'Enraf Nonius FR590'
_diffrn_ambient_temperature             123(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_radiation_probe                 x-ray
_diffrn_detector                        'CCD plate'
_diffrn_detector_area_resol_mean        9
_diffrn_orient_matrix_type
                                     'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11             0.126699
_diffrn_orient_matrix_ub_12             0.42609E-2
_diffrn_orient_matrix_ub_13             0.28838E-2
_diffrn_orient_matrix_ub_21             0.21362E-2
_diffrn_orient_matrix_ub_22             0.779406E-1
_diffrn_orient_matrix_ub_23             -0.263189E-1
_diffrn_orient_matrix_ub_31             -0.103487E-1
_diffrn_orient_matrix_ub_32             0.682554E-1
_diffrn_orient_matrix_ub_33             0.298735E-1
_diffrn_measurement_device              '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type         KappaCCD
_diffrn_measurement_method              'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents         0.0343
_diffrn_reflns_av_unetI/netI            0.0334
_diffrn_reflns_number                   11670
_diffrn_reflns_limit_h_min              -10
_diffrn_reflns_limit_h_max              10
_diffrn_reflns_limit_k_min              -12
_diffrn_reflns_limit_k_max              12
_diffrn_reflns_limit_l_min              -33
_diffrn_reflns_limit_l_max              30
_diffrn_reflns_theta_min                3.44
_diffrn_reflns_theta_max                28.48
_diffrn_reflns_theta_full               28.48
_diffrn_measured_fraction_theta_full
                                        0.99
_diffrn_measured_fraction_theta_max
                                        0.99
_reflns_number_total                    2388
_reflns_number_gt                       2007
_reflns_threshold_expression            >2σ(I)
 
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
 
_computing_data_collection              'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement
                                       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
                             'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
                                   'WinGX publication routines (Farrugia, 1999)'
 
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
 
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
 
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0304P)²+1.6166P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment           constr
_refine_ls_extinction_method            none
_refine_ls_number_reflns                2388
_refine_ls_number_parameters            121
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.045
_refine_ls_R_factor_gt                  0.036
_refine_ls_wR_factor_ref                0.0897
_refine_ls_wR_factor_gt                 0.0857
_refine_ls_goodness_of_fit_ref          1.056
_refine_ls_restrained_S_all             1.056
_refine_ls_shift/su_max                 0.001
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.302
_refine_diff_density_min                -0.41
_refine_diff_density_rms                0.058
 
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
 
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
loop_
    _atom_site_label
    _atom_site_type_symbol
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_disorder_assembly
    _atom_site_disorder_group
Cl1 Cl 0.61649(7) 0.61329(6) 0.807944(18) 0.03855(15) Uani 1 1 d . . .
C2 C 0.5884(2) 0.6171(2) 0.73897(7) 0.0257(4) Uani 1 1 d . . .
C3 C 0.6561(2) 0.5116(2) 0.70811(7) 0.0246(4) Uani 1 1 d . . .
H3 H 0.7163 0.4372 0.7243 0.029 Uiso 1 1 calc R . .
C4 C 0.6345(2) 0.51627(18) 0.65291(7) 0.0213(3) Uani 1 1 d . . .
H4 H 0.6785 0.4445 0.6309 0.026 Uiso 1 1 calc R . .
C5 C 0.5480(2) 0.62693(17) 0.63064(6) 0.0177(3) Uani 1 1 d . . .
C6 C 0.4812(2) 0.73216(19) 0.66127(7) 0.0225(4) Uani 1 1 d . . .
H6 H 0.4229 0.8074 0.645 0.027 Uiso 1 1 calc R . .
C7 C 0.5006(2) 0.7264(2) 0.71657(7) 0.0263(4) Uani 1 1 d . . .
H7 H 0.4538 0.797 0.7386 0.032 Uiso 1 1 calc R . .
N8 N 0.53082(17) 0.63114(14) 0.57234(5) 0.0178(3) Uani 1 1 d . . .
H8A H 0.4677 0.7063 0.5628 0.027 Uiso 1 1 calc R . .
H8B H 0.4784 0.5525 0.5609 0.027 Uiso 1 1 calc R . .
H8C H 0.6357 0.6373 0.5572 0.027 Uiso 1 1 calc R . .
P9 P 0.20068(5) 0.38283(4) 0.535528(16) 0.01615(12) Uani 1 1 d . . .
O10 O 0.14486(14) 0.36387(12) 0.47778(4) 0.0176(2) Uani 1 1 d . . .
O11 O 0.13044(17) 0.52270(16) 0.55844(6) 0.0346(4) Uani 1 1 d . . .
H11 H 0.0388 0.5428 0.5431 0.052 Uiso 1 1 calc R . .
O12 O 0.13484(18) 0.26301(17) 0.57110(5) 0.0367(4) Uani 1 1 d . . .
H12 H 0.0452 0.2304 0.5579 0.055 Uiso 1 1 calc R . .
O13 O 0.39042(14) 0.39068(12) 0.54213(5) 0.0195(3) Uani 1 1 d . . .
 
 
 
#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_distance
    _geom_bond_site_symmetry_2
    _geom_bond_publ_flag
Cl1 C2 1.7424(17) . ?
Cl1 O12 3.2596(16) 3_566 ?
C2 C7 1.380(3) . ?
C2 C3 1.384(3) . ?
C3 C4 1.394(2) . ?
C3 H3 0.95 . ?
C4 C5 1.383(2) . ?
C4 H4 0.95 . ?
C5 C6 1.376(2) . ?
C5 N8 1.4672(19) . ?
C6 C7 1.395(2) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
N8 H8A 0.91 . ?
N8 H8B 0.91 . ?
N8 H8C 0.91 . ?
P9 O13 1.5034(12) . ?
P9 O10 1.5229(11) . ?
P9 O12 1.5485(14) . ?
P9 O11 1.5667(14) . ?
O11 H11 0.84 . ?
O12 H12 0.84 . ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C2 Cl1 O12 156.89(8) . 3_566 ?
C7 C2 C3 121.81(16) . . ?
C7 C2 Cl1 118.88(14) . . ?
C3 C2 Cl1 119.31(14) . . ?
C2 C3 C4 118.90(17) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.02(16) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C6 C5 C4 122.11(15) . . ?
C6 C5 N8 119.97(15) . . ?
C4 C5 N8 117.91(14) . . ?
C5 C6 C7 118.88(16) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C6 119.28(16) . . ?
C2 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C5 N8 H8A 109.5 . . ?
C5 N8 H8B 109.5 . . ?
H8A N8 H8B 109.5 . . ?
C5 N8 H8C 109.5 . . ?
H8A N8 H8C 109.5 . . ?
H8B N8 H8C 109.5 . . ?
O13 P9 O10 113.38(7) . . ?
O13 P9 O12 107.83(7) . . ?
O10 P9 O12 111.15(7) . . ?
O13 P9 O11 105.45(7) . . ?
O10 P9 O11 110.47(7) . . ?
O12 P9 O11 108.28(9) . . ?
P9 O11 H11 109.5 . . ?
P9 O12 H12 109.5 . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
O12 Cl1 C2 C7 -19.7(3) 3_566 . . . ?
O12 Cl1 C2 C3 159.62(14) 3_566 . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
Cl1 C2 C3 C4 -179.36(14) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C3 C4 C5 N8 178.45(15) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
N8 C5 C6 C7 -179.40(15) . . . . ?
C3 C2 C7 C6 -0.9(3) . . . . ?
Cl1 C2 C7 C6 178.38(14) . . . . ?
C5 C6 C7 C2 1.1(3) . . . . ?


data_9
 
_audit_creation_date                    2009-05-27T12:23:29-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety              '2(C12 H11 I N), C2 H6 O, H2 O, 2(Cl)'
_chemical_formula_sum                   'C26 H30 Cl2 I2 N2 O2'
_chemical_formula_weight                727.22
_chemical_compound_source               'synthesis as described'
 
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'P 21/n'
_symmetry_space_group_name_Hall         '-P 2yn'
 
loop_
    _symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                          8.18410(10)
_cell_length_b                          16.9194(2)
_cell_length_c                          20.4094(3)
_cell_angle_alpha                       90
_cell_angle_beta                        94.6030(7)
_cell_angle_gamma                       90
_cell_volume                            2816.98(6)
_cell_formula_units_Z                   4
_cell_measurement_temperature           123(2)
_cell_measurement_reflns_used           7156
_cell_measurement_theta_min             0.407
_cell_measurement_theta_max             28.283
_cell_measurement_wavelength            0.71073
 
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
 
_exptl_crystal_description              block
_exptl_crystal_colour                   'light yellow'
_exptl_crystal_size_max                 0.28
_exptl_crystal_size_mid                 0.16
_exptl_crystal_size_min                 0.14
_exptl_crystal_density_diffrn           1.715
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    1424
_exptl_special_details
;
 ?
;
 
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
 
_exptl_absorpt_coefficient_mu           2.448
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details         '(Blessing et al., 1995)'
_exptl_absorpt_correction_T_max         0.7101
_exptl_absorpt_correction_T_min         0.6132

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
 
_diffrn_source                          'Enraf Nonius FR590'
_diffrn_ambient_temperature             123(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_radiation_probe                 x-ray
_diffrn_detector                        'CCD plate'
_diffrn_detector_area_resol_mean        9
_diffrn_orient_matrix_type
                                     'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11             -0.381894E-1
_diffrn_orient_matrix_ub_12             -0.5866E-3
_diffrn_orient_matrix_ub_13             -0.47785E-1
_diffrn_orient_matrix_ub_21             0.111096
_diffrn_orient_matrix_ub_22             -0.179484E-1
_diffrn_orient_matrix_ub_23             -0.108287E-1
_diffrn_orient_matrix_ub_31             -0.350136E-1
_diffrn_orient_matrix_ub_32             -0.563095E-1
_diffrn_orient_matrix_ub_33             0.39494E-2
_diffrn_measurement_device              '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type         KappaCCD
_diffrn_measurement_method              'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents         0.048
_diffrn_reflns_av_unetI/netI            0.0378
_diffrn_reflns_number                   39929
_diffrn_reflns_limit_h_min              -10
_diffrn_reflns_limit_h_max              10
_diffrn_reflns_limit_k_min              -21
_diffrn_reflns_limit_k_max              21
_diffrn_reflns_limit_l_min              -25
_diffrn_reflns_limit_l_max              26
_diffrn_reflns_theta_min                2.34
_diffrn_reflns_theta_max                27.5
_diffrn_reflns_theta_full               27.5
_diffrn_measured_fraction_theta_full
                                        0.999
_diffrn_measured_fraction_theta_max
                                        0.999
_reflns_number_total                    6478
_reflns_number_gt                       5539
_reflns_threshold_expression            >2σ(I)
 
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
 
_computing_data_collection              'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement
                                       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
                             'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution           'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
                                   'WinGX publication routines (Farrugia, 1999)'
 
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
 
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
 
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0096P)²+8.4237P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment           constr
_refine_ls_extinction_method            none
_refine_ls_number_reflns                6478
_refine_ls_number_parameters            309
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.0425
_refine_ls_R_factor_gt                  0.0332
_refine_ls_wR_factor_ref                0.0679
_refine_ls_wR_factor_gt                 0.0648
_refine_ls_goodness_of_fit_ref          1.038
_refine_ls_restrained_S_all             1.038
_refine_ls_shift/su_max                 0.003
_refine_ls_shift/su_mean                0
_refine_diff_density_max                1.054
_refine_diff_density_min                -0.504
_refine_diff_density_rms                0.114
 
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
 
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
loop_
    _atom_site_label
    _atom_site_type_symbol
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_disorder_assembly
    _atom_site_disorder_group
I1 I 0.63640(3) 0.884179(13) 0.530074(11) 0.01994(6) Uani 1 1 d . . .
C2 C 0.5210(4) 0.78023(19) 0.49404(17) 0.0203(7) Uani 1 1 d . . .
C3 C 0.5740(4) 0.7054(2) 0.51436(18) 0.0242(8) Uani 1 1 d . . .
H3 H 0.6666 0.6994 0.5452 0.029 Uiso 1 1 calc R . .
C4 C 0.4895(5) 0.6398(2) 0.48891(18) 0.0251(8) Uani 1 1 d . . .
H4 H 0.5253 0.5882 0.5016 0.03 Uiso 1 1 calc R . .
C5 C 0.3542(4) 0.6493(2) 0.44532(18) 0.0229(7) Uani 1 1 d . . .
H5 H 0.2953 0.6043 0.4284 0.028 Uiso 1 1 calc R . .
N6 N 0.3048(3) 0.72261(16) 0.42650(13) 0.0181(6) Uani 1 1 d . . .
C7 C 0.3849(4) 0.78761(19) 0.44978(16) 0.0183(7) Uani 1 1 d . . .
H7 H 0.3479 0.8385 0.4358 0.022 Uiso 1 1 calc R . .
C8 C 0.1589(4) 0.7332(2) 0.37843(16) 0.0213(7) Uani 1 1 d . . .
H8A H 0.109 0.7857 0.3849 0.026 Uiso 1 1 calc R . .
H8B H 0.076 0.6923 0.3859 0.026 Uiso 1 1 calc R . .
C9 C 0.2094(4) 0.7268(2) 0.30913(17) 0.0199(7) Uani 1 1 d . . .
C10 C 0.2157(4) 0.6528(2) 0.27946(18) 0.0234(7) Uani 1 1 d . . .
H10 H 0.1824 0.6069 0.3017 0.028 Uiso 1 1 calc R . .
C11 C 0.2711(4) 0.6465(2) 0.21707(18) 0.0259(8) Uani 1 1 d . . .
H11 H 0.2766 0.5962 0.1968 0.031 Uiso 1 1 calc R . .
C12 C 0.3180(4) 0.7130(2) 0.18450(18) 0.0259(8) Uani 1 1 d . . .
H12 H 0.357 0.7081 0.1421 0.031 Uiso 1 1 calc R . .
C13 C 0.3089(5) 0.7868(2) 0.21296(18) 0.0284(8) Uani 1 1 d . . .
H13 H 0.3399 0.8325 0.1899 0.034 Uiso 1 1 calc R . .
C14 C 0.2543(5) 0.7937(2) 0.27534(18) 0.0257(8) Uani 1 1 d . . .
H14 H 0.2475 0.8444 0.295 0.031 Uiso 1 1 calc R . .
I15 I 0.50164(3) 0.468706(13) 0.328724(12) 0.02390(6) Uani 1 1 d . . .
C16 C 0.6918(4) 0.4790(2) 0.26610(17) 0.0206(7) Uani 1 1 d . . .
C17 C 0.8554(4) 0.4657(2) 0.28693(19) 0.0249(8) Uani 1 1 d . . .
H17 H 0.8861 0.4513 0.3312 0.03 Uiso 1 1 calc R . .
C18 C 0.9729(4) 0.4738(2) 0.2424(2) 0.0277(8) Uani 1 1 d . . .
H18 H 1.0847 0.4637 0.2559 0.033 Uiso 1 1 calc R . .
C19 C 0.9295(4) 0.4963(2) 0.1790(2) 0.0267(8) Uani 1 1 d . . .
H19 H 1.0107 0.5021 0.1487 0.032 Uiso 1 1 calc R . .
N20 N 0.7697(4) 0.51042(16) 0.15987(15) 0.0207(6) Uani 1 1 d . . .
C21 C 0.6504(4) 0.50152(19) 0.20178(18) 0.0215(7) Uani 1 1 d . . .
H21 H 0.539 0.5107 0.187 0.026 Uiso 1 1 calc R . .
C22 C 0.7198(5) 0.5411(2) 0.09279(18) 0.0251(8) Uani 1 1 d . . .
H22A H 0.6163 0.5154 0.0759 0.03 Uiso 1 1 calc R . .
H22B H 0.8051 0.5275 0.0629 0.03 Uiso 1 1 calc R . .
C23 C 0.6960(4) 0.6297(2) 0.09319(18) 0.0223(7) Uani 1 1 d . . .
C24 C 0.5889(5) 0.6619(2) 0.04427(19) 0.0279(8) Uani 1 1 d . . .
H24 H 0.5313 0.6283 0.0131 0.033 Uiso 1 1 calc R . .
C25 C 0.5654(5) 0.7431(2) 0.0407(2) 0.0332(9) Uani 1 1 d . . .
H25 H 0.4908 0.7648 0.0074 0.04 Uiso 1 1 calc R . .
C26 C 0.6498(6) 0.7924(2) 0.0853(2) 0.0366(10) Uani 1 1 d . . .
H26 H 0.6354 0.848 0.0823 0.044 Uiso 1 1 calc R . .
C27 C 0.7567(6) 0.7600(2) 0.1348(2) 0.0377(10) Uani 1 1 d . . .
H27 H 0.8141 0.7938 0.1659 0.045 Uiso 1 1 calc R . .
C28 C 0.7795(5) 0.6788(2) 0.1388(2) 0.0305(9) Uani 1 1 d . . .
H28 H 0.852 0.657 0.1728 0.037 Uiso 1 1 calc R . .
O29 O 0.8036(4) 0.64815(19) 0.31854(17) 0.0452(8) Uani 1 1 d . . .
H29 H 0.8301 0.6334 0.3572 0.068 Uiso 1 1 calc R . .
C30 C 0.6769(5) 0.7036(3) 0.3186(2) 0.0373(10) Uani 1 1 d . . .
H30A H 0.5963 0.6854 0.349 0.045 Uiso 1 1 calc R . .
H30B H 0.6201 0.7063 0.274 0.045 Uiso 1 1 calc R . .
C31 C 0.7336(6) 0.7848(3) 0.3387(3) 0.0496(12) Uani 1 1 d . . .
H31A H 0.813 0.8036 0.3087 0.074 Uiso 1 1 calc R . .
H31B H 0.7855 0.7833 0.3836 0.074 Uiso 1 1 calc R . .
H31C H 0.6394 0.8208 0.3368 0.074 Uiso 1 1 calc R . .
Cl1 Cl 0.80018(10) 1.03456(5) 0.59868(4) 0.02112(17) Uani 1 1 d . . .
Cl2 Cl 0.18669(10) 0.45915(5) 0.41363(4) 0.02336(18) Uani 1 1 d . . .
O3 O 0.9156(4) 0.58685(19) 0.44223(15) 0.0458(8) Uani 1 1 d . . .
H3A H 0.9842 0.551 0.4322 0.069 Uiso 1 1 d . . .
H3B H 0.8876 0.5754 0.4808 0.069 Uiso 1 1 d . . .
 
 
 
#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_distance
    _geom_bond_site_symmetry_2
    _geom_bond_publ_flag
I1 C2 2.101(3) . ?
C2 C7 1.382(5) . ?
C2 C3 1.391(5) . ?
C3 C4 1.387(5) . ?
C3 H3 0.95 . ?
C4 C5 1.373(5) . ?
C4 H4 0.95 . ?
C5 N6 1.351(4) . ?
C5 H5 0.95 . ?
N6 C7 1.347(4) . ?
N6 C8 1.495(4) . ?
C7 H7 0.95 . ?
C8 C9 1.509(5) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C14 1.391(5) . ?
C9 C10 1.394(5) . ?
C10 C11 1.390(5) . ?
C10 H10 0.95 . ?
C11 C12 1.376(5) . ?
C11 H11 0.95 . ?
C12 C13 1.381(5) . ?
C12 H12 0.95 . ?
C13 C14 1.388(5) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
I15 C16 2.099(3) . ?
C16 C21 1.383(5) . ?
C16 C17 1.390(5) . ?
C17 C18 1.382(5) . ?
C17 H17 0.95 . ?
C18 C19 1.367(6) . ?
C18 H18 0.95 . ?
C19 N20 1.355(5) . ?
C19 H19 0.95 . ?
N20 C21 1.357(4) . ?
N20 C22 1.490(5) . ?
C21 H21 0.95 . ?
C22 C23 1.512(5) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 C24 1.386(5) . ?
C23 C28 1.387(5) . ?
C24 C25 1.389(5) . ?
C24 H24 0.95 . ?
C25 C26 1.377(6) . ?
C25 H25 0.95 . ?
C26 C27 1.394(6) . ?
C26 H26 0.95 . ?
C27 C28 1.388(5) . ?
C27 H27 0.95 . ?
C28 H28 0.95 . ?
O29 C30 1.399(5) . ?
O29 H29 0.84 . ?
C30 C31 1.497(6) . ?
C30 H30A 0.99 . ?
C30 H30B 0.99 . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?
O3 H3A 0.862 . ?
O3 H3B 0.860 . ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C7 C2 C3 119.5(3) . . ?
C7 C2 I1 118.0(2) . . ?
C3 C2 I1 122.5(3) . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120 . . ?
C3 C4 H4 120 . . ?
N6 C5 C4 119.9(3) . . ?
N6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 N6 C5 121.6(3) . . ?
C7 N6 C8 118.3(3) . . ?
C5 N6 C8 120.1(3) . . ?
N6 C7 C2 120.0(3) . . ?
N6 C7 H7 120 . . ?
C2 C7 H7 120 . . ?
N6 C8 C9 110.0(3) . . ?
N6 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
N6 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C14 C9 C10 119.7(3) . . ?
C14 C9 C8 120.6(3) . . ?
C10 C9 C8 119.6(3) . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C9 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C21 C16 C17 119.4(3) . . ?
C21 C16 I15 117.6(3) . . ?
C17 C16 I15 122.9(3) . . ?
C18 C17 C16 119.1(4) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
N20 C19 C18 119.6(3) . . ?
N20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 N20 C21 121.6(3) . . ?
C19 N20 C22 120.9(3) . . ?
C21 N20 C22 117.4(3) . . ?
N20 C21 C16 119.7(3) . . ?
N20 C21 H21 120.2 . . ?
C16 C21 H21 120.2 . . ?
N20 C22 C23 111.5(3) . . ?
N20 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
N20 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108 . . ?
C24 C23 C28 119.8(3) . . ?
C24 C23 C22 117.4(3) . . ?
C28 C23 C22 122.8(3) . . ?
C23 C24 C25 120.2(4) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 120.3(4) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 119.6(4) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C28 C27 C26 120.3(4) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C23 C28 C27 119.8(4) . . ?
C23 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C30 O29 H29 109.5 . . ?
O29 C30 C31 113.7(4) . . ?
O29 C30 H30A 108.8 . . ?
C31 C30 H30A 108.8 . . ?
O29 C30 H30B 108.8 . . ?
C31 C30 H30B 108.8 . . ?
H30A C30 H30B 107.7 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
H3A O3 H3B 106.5 . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C7 C2 C3 C4 0.7(5) . . . . ?
I1 C2 C3 C4 179.0(3) . . . . ?
C2 C3 C4 C5 -1.2(5) . . . . ?
C3 C4 C5 N6 1.0(5) . . . . ?
C4 C5 N6 C7 -0.4(5) . . . . ?
C4 C5 N6 C8 179.2(3) . . . . ?
C5 N6 C7 C2 -0.1(5) . . . . ?
C8 N6 C7 C2 -179.7(3) . . . . ?
C3 C2 C7 N6 -0.1(5) . . . . ?
I1 C2 C7 N6 -178.5(2) . . . . ?
C7 N6 C8 C9 94.5(3) . . . . ?
C5 N6 C8 C9 -85.1(4) . . . . ?
N6 C8 C9 C14 -91.4(4) . . . . ?
N6 C8 C9 C10 86.7(4) . . . . ?
C14 C9 C10 C11 1.8(5) . . . . ?
C8 C9 C10 C11 -176.4(3) . . . . ?
C9 C10 C11 C12 -0.6(5) . . . . ?
C10 C11 C12 C13 -0.8(6) . . . . ?
C11 C12 C13 C14 1.0(6) . . . . ?
C12 C13 C14 C9 0.2(6) . . . . ?
C10 C9 C14 C13 -1.6(5) . . . . ?
C8 C9 C14 C13 176.6(3) . . . . ?
C21 C16 C17 C18 -1.3(5) . . . . ?
I15 C16 C17 C18 180.0(3) . . . . ?
C16 C17 C18 C19 1.5(5) . . . . ?
C17 C18 C19 N20 -0.3(5) . . . . ?
C18 C19 N20 C21 -1.1(5) . . . . ?
C18 C19 N20 C22 175.2(3) . . . . ?
C19 N20 C21 C16 1.2(5) . . . . ?
C22 N20 C21 C16 -175.1(3) . . . . ?
C17 C16 C21 N20 0.0(5) . . . . ?
I15 C16 C21 N20 178.7(2) . . . . ?
C19 N20 C22 C23 -97.7(4) . . . . ?
C21 N20 C22 C23 78.7(4) . . . . ?
N20 C22 C23 C24 -153.7(3) . . . . ?
N20 C22 C23 C28 28.1(5) . . . . ?
C28 C23 C24 C25 0.2(5) . . . . ?
C22 C23 C24 C25 -178.0(3) . . . . ?
C23 C24 C25 C26 0.8(6) . . . . ?
C24 C25 C26 C27 -1.3(6) . . . . ?
C25 C26 C27 C28 0.8(6) . . . . ?
C24 C23 C28 C27 -0.8(6) . . . . ?
C22 C23 C28 C27 177.4(4) . . . . ?
C26 C27 C28 C23 0.3(6) . . . . ?
 

data_10
 
_audit_creation_date                    2009-08-25T16:17:53-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                '4(C5 H5 I N), C2 H6 O, 4(Cl)'
_chemical_formula_sum                   'C22 H26 Cl4 I4 N4 O'
_chemical_formula_weight                1011.87
_chemical_compound_source               'synthesis as described'
 
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting                  triclinic
_symmetry_space_group_name_H-M          'P -1'
_symmetry_space_group_name_Hall         '-P 1'
_symmetry_Int_Tables_number             2
 
loop_
    _symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
 
_cell_length_a                          8.19130(10)
_cell_length_b                          11.4208(2)
_cell_length_c                          17.9429(3)
_cell_angle_alpha                       80.0270(10)
_cell_angle_beta                        78.2170(10)
_cell_angle_gamma                       76.3020(10)
_cell_volume                            1582.66(4)
_cell_formula_units_Z                   2
_cell_measurement_temperature           123(2)
_cell_measurement_reflns_used           5406
_cell_measurement_theta_min             0.407
_cell_measurement_theta_max             28.283
_cell_measurement_wavelength            0.71073
 
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
 
_exptl_crystal_description              block
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.40
_exptl_crystal_size_mid                 0.28
_exptl_crystal_size_min                 0.20
_exptl_crystal_density_diffrn           2.123
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    948
_exptl_special_details
;
 ?
;
 
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
 
_exptl_absorpt_coefficient_mu           4.298
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min         0.5641
_exptl_absorpt_correction_T_max         0.7456

 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
 
_diffrn_source                          'Enraf Nonius FR590'
_diffrn_ambient_temperature             123(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_radiation_probe                 x-ray
_diffrn_detector                        'CCD plate'
_diffrn_detector_area_resol_mean        9
_diffrn_orient_matrix_type
                                     'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11             0.121803E-1
_diffrn_orient_matrix_ub_12             -0.146551E-1
_diffrn_orient_matrix_ub_13             0.553704E-1
_diffrn_orient_matrix_ub_21             0.126925
_diffrn_orient_matrix_ub_22             -0.190097E-1
_diffrn_orient_matrix_ub_23             -0.151263E-1
_diffrn_orient_matrix_ub_31             0.19285E-2
_diffrn_orient_matrix_ub_32             0.876834E-1
_diffrn_orient_matrix_ub_33             -0.18396E-2
_diffrn_measurement_device              '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type         KappaCCD
_diffrn_measurement_method              'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents         0.0292
_diffrn_reflns_av_unetI/netI            0.0362
_diffrn_reflns_number                   19765
_diffrn_reflns_limit_h_min              -10
_diffrn_reflns_limit_h_max              10
_diffrn_reflns_limit_k_min              -14
_diffrn_reflns_limit_k_max              9
_diffrn_reflns_limit_l_min              -22
_diffrn_reflns_limit_l_max              23
_diffrn_reflns_theta_min                1.17
_diffrn_reflns_theta_max                27.5
_diffrn_reflns_theta_full               25
_diffrn_measured_fraction_theta_full
                                        0.982
_diffrn_measured_fraction_theta_max
                                        0.933
_reflns_number_total                    6784
_reflns_number_gt                       5366
_reflns_threshold_expression            >2σ(I)
 
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
 
_computing_data_collection              'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement
                                       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
                             'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
                                   'WinGX publication routines (Farrugia, 1999)'
 
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
 
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
 
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0133P)²+4.8563P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment           constr
_refine_ls_extinction_method            none
_refine_ls_number_reflns                6784
_refine_ls_number_parameters            318
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.0442
_refine_ls_R_factor_gt                  0.0326
_refine_ls_wR_factor_ref                0.0722
_refine_ls_wR_factor_gt                 0.0667
_refine_ls_goodness_of_fit_ref          1.022
_refine_ls_restrained_S_all             1.022
_refine_ls_shift/su_max                 0.001
_refine_ls_shift/su_mean                0
_refine_diff_density_max                1.131
_refine_diff_density_min                -0.915
_refine_diff_density_rms                0.149
 
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
 
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
loop_
    _atom_site_label
    _atom_site_type_symbol
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_disorder_assembly
    _atom_site_disorder_group
Cl1 Cl 0.78582(12) -0.27005(9) -0.11410(5) 0.0221(2) Uani 1 1 d . . .
Cl2 Cl 1.28917(12) 0.06156(9) -0.05190(5) 0.0216(2) Uani 1 1 d . . .
Cl3 Cl 0.70922(12) -0.05837(9) 0.55127(5) 0.0212(2) Uani 1 1 d . . .
Cl4 Cl 1.79827(12) -0.27448(9) 0.38542(5) 0.0226(2) Uani 1 1 d . . .
I1 I 1.09287(3) -0.32305(2) -0.020462(15) 0.02443(8) Uani 1 1 d . . .
C2 C 1.3052(5) -0.3450(4) 0.0329(2) 0.0185(8) Uani 1 1 d . . .
C3 C 1.3569(5) -0.4473(4) 0.0833(2) 0.0264(9) Uani 1 1 d . . .
H3 H 1.2967 -0.5116 0.0945 0.032 Uiso 1 1 calc R . .
C4 C 1.4970(6) -0.4550(4) 0.1174(3) 0.0317(10) Uani 1 1 d . . .
H4 H 1.5326 -0.5245 0.1524 0.038 Uiso 1 1 calc R . .
C5 C 1.5845(5) -0.3622(4) 0.1005(2) 0.0262(9) Uani 1 1 d . . .
H5 H 1.6813 -0.367 0.1233 0.031 Uiso 1 1 calc R . .
N6 N 1.5313(4) -0.2653(3) 0.05147(19) 0.0243(7) Uani 1 1 d . . .
H6 H 1.5878 -0.2061 0.041 0.029 Uiso 1 1 calc R . .
C7 C 1.3967(5) -0.2534(4) 0.0174(2) 0.0223(8) Uani 1 1 d . . .
H7 H 1.3639 -0.1826 -0.0172 0.027 Uiso 1 1 calc R . .
I8 I 1.49511(3) -0.19037(2) 0.290109(14) 0.02134(7) Uani 1 1 d . . .
C9 C 1.2934(5) -0.1335(3) 0.2263(2) 0.0197(8) Uani 1 1 d . . .
C10 C 1.1453(5) -0.1785(4) 0.2485(3) 0.0288(10) Uani 1 1 d . . .
H10 H 1.1314 -0.2352 0.2936 0.035 Uiso 1 1 calc R . .
C11 C 1.0178(5) -0.1398(4) 0.2041(3) 0.0315(10) Uani 1 1 d . . .
H11 H 0.9144 -0.1682 0.2192 0.038 Uiso 1 1 calc R . .
C12 C 1.0418(5) -0.0601(4) 0.1381(3) 0.0293(10) Uani 1 1 d . . .
H12 H 0.9576 -0.0355 0.1059 0.035 Uiso 1 1 calc R . .
N13 N 1.1861(4) -0.0176(3) 0.11977(19) 0.0245(7) Uani 1 1 d . . .
H13 H 1.1991 0.0352 0.0782 0.029 Uiso 1 1 calc R . .
C14 C 1.3116(5) -0.0515(4) 0.1617(2) 0.0198(8) Uani 1 1 d . . .
H14 H 1.4118 -0.019 0.1466 0.024 Uiso 1 1 calc R . .
I15 I 0.51463(3) 0.19391(2) 0.208569(14) 0.02140(7) Uani 1 1 d . . .
C16 C 0.7153(5) 0.1342(4) 0.2721(2) 0.0197(8) Uani 1 1 d . . .
C17 C 0.6924(5) 0.0555(4) 0.3388(2) 0.0203(8) Uani 1 1 d . . .
H17 H 0.5891 0.0271 0.3549 0.024 Uiso 1 1 calc R . .
N18 N 0.8170(4) 0.0195(3) 0.38068(19) 0.0245(7) Uani 1 1 d . . .
H18 H 0.8 -0.0303 0.4235 0.029 Uiso 1 1 calc R . .
C19 C 0.9662(5) 0.0550(4) 0.3612(3) 0.0283(10) Uani 1 1 d . . .
H19 H 1.0503 0.0279 0.3933 0.034 Uiso 1 1 calc R . .
C20 C 0.9959(5) 0.1317(4) 0.2936(3) 0.0294(10) Uani 1 1 d . . .
H20 H 1.102 0.1563 0.2778 0.035 Uiso 1 1 calc R . .
C21 C 0.8698(5) 0.1718(4) 0.2494(2) 0.0250(9) Uani 1 1 d . . .
H21 H 0.8882 0.2254 0.2032 0.03 Uiso 1 1 calc R . .
I22 I 0.89852(3) 0.31963(2) 0.516289(15) 0.02589(8) Uani 1 1 d . . .
C23 C 0.6838(5) 0.3461(4) 0.4639(2) 0.0208(8) Uani 1 1 d . . .
C24 C 0.5894(5) 0.2559(4) 0.4793(2) 0.0228(8) Uani 1 1 d . . .
H24 H 0.6215 0.1841 0.5132 0.027 Uiso 1 1 calc R . .
N25 N 0.4527(4) 0.2715(3) 0.44587(19) 0.0248(7) Uani 1 1 d . . .
H25 H 0.3954 0.2129 0.4552 0.03 Uiso 1 1 calc R . .
C26 C 0.3985(5) 0.3714(4) 0.3990(2) 0.0264(9) Uani 1 1 d . . .
H26 H 0.2993 0.3791 0.3774 0.032 Uiso 1 1 calc R . .
C27 C 0.4884(5) 0.4630(4) 0.3825(3) 0.0284(9) Uani 1 1 d . . .
H27 H 0.4529 0.5341 0.3486 0.034 Uiso 1 1 calc R . .
C28 C 0.6314(5) 0.4508(4) 0.4156(2) 0.0260(9) Uani 1 1 d . . .
H28 H 0.6932 0.5141 0.4052 0.031 Uiso 1 1 calc R . .
O29 O -0.1072(5) 0.4695(4) 0.6934(2) 0.0556(10) Uani 1 1 d . . .
H29 H -0.0263 0.4226 0.6695 0.083 Uiso 1 1 calc R . .
C30 C -0.0437(7) 0.5445(5) 0.7264(3) 0.0465(14) Uani 1 1 d . . .
H30A H -0.1405 0.5995 0.7539 0.056 Uiso 1 1 calc R . .
H30B H 0.0178 0.5955 0.685 0.056 Uiso 1 1 calc R . .
C31 C 0.0761(8) 0.4805(6) 0.7820(3) 0.070(2) Uani 1 1 d . . .
H31A H 0.0218 0.4225 0.82 0.105 Uiso 1 1 calc R . .
H31B H 0.1018 0.5407 0.8083 0.105 Uiso 1 1 calc R . .
H31C H 0.1821 0.4371 0.7538 0.105 Uiso 1 1 calc R . .
 
 
 
#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_distance
    _geom_bond_site_symmetry_2
    _geom_bond_publ_flag
I1 C2 2.096(4) . ?
C2 C3 1.385(5) . ?
C2 C7 1.386(5) . ?
C3 C4 1.384(6) . ?
C3 H3 0.95 . ?
C4 C5 1.374(6) . ?
C4 H4 0.95 . ?
C5 N6 1.334(5) . ?
C5 H5 0.95 . ?
N6 C7 1.335(5) . ?
N6 H6 0.88 . ?
C7 H7 0.95 . ?
I8 C9 2.114(4) . ?
C9 C14 1.365(5) . ?
C9 C10 1.387(6) . ?
C10 C11 1.386(6) . ?
C10 H10 0.95 . ?
C11 C12 1.373(6) . ?
C11 H11 0.95 . ?
C12 N13 1.342(5) . ?
C12 H12 0.95 . ?
N13 C14 1.341(5) . ?
N13 H13 0.88 . ?
C14 H14 0.95 . ?
I15 C16 2.105(4) . ?
C16 C17 1.374(5) . ?
C16 C21 1.392(5) . ?
C17 N18 1.335(5) . ?
C17 H17 0.95 . ?
N18 C19 1.338(5) . ?
N18 H18 0.88 . ?
C19 C20 1.382(6) . ?
C19 H19 0.95 . ?
C20 C21 1.375(6) . ?
C20 H20 0.95 . ?
C21 H21 0.95 . ?
I22 C23 2.096(4) . ?
C23 C28 1.383(6) . ?
C23 C24 1.388(6) . ?
C24 N25 1.338(5) . ?
C24 H24 0.95 . ?
N25 C26 1.336(5) . ?
N25 H25 0.88 . ?
C26 C27 1.376(6) . ?
C26 H26 0.95 . ?
C27 C28 1.387(6) . ?
C27 H27 0.95 . ?
C28 H28 0.95 . ?
O29 C30 1.366(6) . ?
O29 H29 0.84 . ?
C30 C31 1.517(7) . ?
C30 H30A 0.99 . ?
C30 H30B 0.99 . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C3 C2 C7 118.8(4) . . ?
C3 C2 I1 122.5(3) . . ?
C7 C2 I1 118.7(3) . . ?
C4 C3 C2 119.4(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 120 . . ?
C3 C4 H4 120 . . ?
N6 C5 C4 118.8(4) . . ?
N6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 N6 C7 123.4(4) . . ?
C5 N6 H6 118.3 . . ?
C7 N6 H6 118.3 . . ?
N6 C7 C2 119.5(4) . . ?
N6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
C14 C9 C10 119.9(4) . . ?
C14 C9 I8 118.7(3) . . ?
C10 C9 I8 121.4(3) . . ?
C11 C10 C9 119.2(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C12 C11 C10 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
N13 C12 C11 118.9(4) . . ?
N13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C14 N13 C12 123.3(4) . . ?
C14 N13 H13 118.3 . . ?
C12 N13 H13 118.3 . . ?
N13 C14 C9 119.0(4) . . ?
N13 C14 H14 120.5 . . ?
C9 C14 H14 120.5 . . ?
C17 C16 C21 118.8(4) . . ?
C17 C16 I15 118.7(3) . . ?
C21 C16 I15 122.5(3) . . ?
N18 C17 C16 119.3(4) . . ?
N18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 N18 C19 123.6(4) . . ?
C17 N18 H18 118.2 . . ?
C19 N18 H18 118.2 . . ?
N18 C19 C20 118.9(4) . . ?
N18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C21 C20 C19 119.1(4) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C20 C21 C16 120.3(4) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C28 C23 C24 118.9(4) . . ?
C28 C23 I22 122.5(3) . . ?
C24 C23 I22 118.6(3) . . ?
N25 C24 C23 119.1(4) . . ?
N25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C26 N25 C24 123.5(4) . . ?
C26 N25 H25 118.3 . . ?
C24 N25 H25 118.3 . . ?
N25 C26 C27 119.1(4) . . ?
N25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C26 C27 C28 119.5(4) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C23 C28 C27 119.8(4) . . ?
C23 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C30 O29 H29 109.5 . . ?
O29 C30 C31 115.2(5) . . ?
O29 C30 H30A 108.5 . . ?
C31 C30 H30A 108.5 . . ?
O29 C30 H30B 108.5 . . ?
C31 C30 H30B 108.5 . . ?
H30A C30 H30B 107.5 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C7 C2 C3 C4 0.6(6) . . . . ?
I1 C2 C3 C4 -179.1(3) . . . . ?
C2 C3 C4 C5 -0.6(7) . . . . ?
C3 C4 C5 N6 0.4(7) . . . . ?
C4 C5 N6 C7 -0.2(6) . . . . ?
C5 N6 C7 C2 0.1(6) . . . . ?
C3 C2 C7 N6 -0.3(6) . . . . ?
I1 C2 C7 N6 179.3(3) . . . . ?
C14 C9 C10 C11 0.4(7) . . . . ?
I8 C9 C10 C11 -179.0(3) . . . . ?
C9 C10 C11 C12 1.6(7) . . . . ?
C10 C11 C12 N13 -2.7(7) . . . . ?
C11 C12 N13 C14 1.9(7) . . . . ?
C12 N13 C14 C9 0.0(6) . . . . ?
C10 C9 C14 N13 -1.2(6) . . . . ?
I8 C9 C14 N13 178.2(3) . . . . ?
C21 C16 C17 N18 1.5(6) . . . . ?
I15 C16 C17 N18 -178.2(3) . . . . ?
C16 C17 N18 C19 -0.6(6) . . . . ?
C17 N18 C19 C20 -1.0(7) . . . . ?
N18 C19 C20 C21 1.7(7) . . . . ?
C19 C20 C21 C16 -0.9(7) . . . . ?
C17 C16 C21 C20 -0.7(6) . . . . ?
I15 C16 C21 C20 179.0(3) . . . . ?
C28 C23 C24 N25 1.4(6) . . . . ?
I22 C23 C24 N25 -179.6(3) . . . . ?
C23 C24 N25 C26 -1.5(6) . . . . ?
C24 N25 C26 C27 1.3(6) . . . . ?
N25 C26 C27 C28 -1.0(6) . . . . ?
C24 C23 C28 C27 -1.2(6) . . . . ?
I22 C23 C28 C27 179.9(3) . . . . ?
C26 C27 C28 C23 1.0(6) . . . . ?
 

data_13
 
_audit_creation_date                    2009-05-27T16:30:53-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C8 H4 N O6, C5 H5 I N'
_chemical_formula_sum                   'C13 H9 I N2 O6'
_chemical_formula_weight                416.12
_chemical_compound_source               'synthesis as described'
 
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting                  triclinic
_symmetry_space_group_name_H-M          'P -1'
_symmetry_space_group_name_Hall         '-P 1'
 
loop_
    _symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
 
_cell_length_a                          8.1247(2)
_cell_length_b                          8.4128(2)
_cell_length_c                          11.7526(3)
_cell_angle_alpha                       87.9511(16)
_cell_angle_beta                        73.0323(19)
_cell_angle_gamma                       62.9872(16)
_cell_volume                            680.09(3)
_cell_formula_units_Z                   2
_cell_measurement_temperature           123(2)
_cell_measurement_reflns_used           2657
_cell_measurement_theta_min             0.407
_cell_measurement_theta_max             26.733
_cell_measurement_wavelength            0.71073
 
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
 
_exptl_crystal_description              block
_exptl_crystal_colour                   colorless
_exptl_crystal_size_max                 0.25
_exptl_crystal_size_mid                 0.2
_exptl_crystal_size_min                 0.2
_exptl_crystal_density_diffrn           2.032
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    404
_exptl_special_details
;
 ?
;
 
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
 
_exptl_absorpt_coefficient_mu           2.388
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details         '(Blessing et al., 1995)'
_exptl_absorpt_correction_T_max         0.6204
_exptl_absorpt_correction_T_min         0.5054

 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
 
_diffrn_source                          'Enraf Nonius FR590'
_diffrn_ambient_temperature             123(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_radiation_probe                 x-ray
_diffrn_detector                        'CCD plate'
_diffrn_detector_area_resol_mean        9
_diffrn_orient_matrix_type
                                     'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11             0.125264
_diffrn_orient_matrix_ub_12             -0.384292E-1
_diffrn_orient_matrix_ub_13             0.174013E-1
_diffrn_orient_matrix_ub_21             -0.733514E-1
_diffrn_orient_matrix_ub_22             0.479167E-1
_diffrn_orient_matrix_ub_23             0.860717E-1
_diffrn_orient_matrix_ub_31             0.6108E-2
_diffrn_orient_matrix_ub_32             -0.119421
_diffrn_orient_matrix_ub_33             0.174984E-1
_diffrn_measurement_device              '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type         KappaCCD
_diffrn_measurement_method              'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents         0.0308
_diffrn_reflns_av_unetI/netI            0.0346
_diffrn_reflns_number                   7548
_diffrn_reflns_limit_h_min              -7
_diffrn_reflns_limit_h_max              9
_diffrn_reflns_limit_k_min              -9
_diffrn_reflns_limit_k_max              9
_diffrn_reflns_limit_l_min              -12
_diffrn_reflns_limit_l_max              13
_diffrn_reflns_theta_min                2.74
_diffrn_reflns_theta_max                25
_diffrn_reflns_theta_full               25
_diffrn_measured_fraction_theta_full
                                        0.971
_diffrn_measured_fraction_theta_max
                                        0.971
_reflns_number_total                    2322
_reflns_number_gt                       2198
_reflns_threshold_expression            >2σ(I)
 
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
 
_computing_data_collection              'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement
                                       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
                             'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution           'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
                                   'WinGX publication routines (Farrugia, 1999)'
 
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
 
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
 
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0000P)²+1.1926P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment           mixed
_refine_ls_extinction_method            none
_refine_ls_number_reflns                2322
_refine_ls_number_parameters            207
_refine_ls_number_restraints            1
_refine_ls_R_factor_all                 0.025
_refine_ls_R_factor_gt                  0.0228
_refine_ls_wR_factor_ref                0.0504
_refine_ls_wR_factor_gt                 0.0496
_refine_ls_goodness_of_fit_ref          1.071
_refine_ls_restrained_S_all             1.071
_refine_ls_shift/su_max                 0.001
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.593
_refine_diff_density_min                -0.406
_refine_diff_density_rms                0.087
 
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
 
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
loop_
    _atom_site_label
    _atom_site_type_symbol
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_disorder_assembly
    _atom_site_disorder_group
I1 I 0.03873(3) 0.73071(3) 0.974460(17) 0.01818(8) Uani 1 1 d . . .
C3 C 0.3241(4) 0.2077(4) 0.7049(3) 0.0170(6) Uani 1 1 d . . .
H3 H 0.2123 0.2404 0.7728 0.02 Uiso 1 1 calc R . .
O4 O 0.8030(3) 0.1467(3) 0.3167(2) 0.0391(7) Uani 1 1 d . . .
O5 O 0.3696(3) -0.0060(3) 0.89710(18) 0.0196(5) Uani 1 1 d . . .
C6 C 0.4943(4) 0.0507(4) 0.6991(3) 0.0154(6) Uani 1 1 d . . .
O8 O -0.0111(3) 0.5075(3) 0.7114(2) 0.0267(6) Uani 1 1 d . . .
H8 H -0.098(7) 0.592(7) 0.713(4) 0.059(16) Uiso 1 1 d . . .
C9 C 0.6460(4) 0.1139(4) 0.5086(3) 0.0163(6) Uani 1 1 d . . .
N10 N 0.5528(3) 0.2398(3) 0.9476(2) 0.0157(5) Uani 1 1 d D . .
H10 H 0.586(5) 0.159(4) 0.998(3) 0.038(11) Uiso 1 1 d D . .
O11 O 0.9656(3) -0.0743(3) 0.4003(2) 0.0380(7) Uani 1 1 d . . .
O13 O 0.1280(3) 0.5874(3) 0.5410(2) 0.0346(6) Uani 1 1 d . . .
C14 C 0.5052(4) -0.0675(4) 0.7989(3) 0.0179(7) Uani 1 1 d . . .
O16 O 0.6472(3) -0.2190(3) 0.7788(2) 0.0340(6) Uani 1 1 d . . .
C18 C 0.3159(4) 0.3170(4) 0.6127(3) 0.0166(6) Uani 1 1 d . . .
N19 N 0.8167(4) 0.0601(4) 0.4012(2) 0.0216(6) Uani 1 1 d . . .
C20 C 0.6576(4) 0.0031(4) 0.5986(3) 0.0167(6) Uani 1 1 d . . .
H20 H 0.7745 -0.1036 0.5924 0.02 Uiso 1 1 calc R . .
C23 C 0.6841(4) 0.2277(4) 0.8433(3) 0.0185(7) Uani 1 1 d . . .
H23 H 0.809 0.1261 0.8197 0.022 Uiso 1 1 calc R . .
C25 C 0.1350(4) 0.4855(4) 0.6166(3) 0.0196(7) Uani 1 1 d . . .
C26 C 0.4795(4) 0.2709(4) 0.5131(3) 0.0189(7) Uani 1 1 d . . .
H26 H 0.4768 0.345 0.45 0.023 Uiso 1 1 calc R . .
C27 C 0.3193(4) 0.5162(4) 0.9120(3) 0.0155(6) Uani 1 1 d . . .
C28 C 0.3736(4) 0.3787(4) 0.9829(3) 0.0164(6) Uani 1 1 d . . .
H28 H 0.2835 0.3827 1.057 0.02 Uiso 1 1 calc R . .
C444 C 0.6375(4) 0.3636(4) 0.7698(3) 0.0189(7) Uani 1 1 d . . .
H444 H 0.7306 0.3567 0.6964 0.023 Uiso 1 1 calc R . .
C333 C 0.4542(4) 0.5091(4) 0.8047(3) 0.0187(7) Uani 1 1 d . . .
H333 H 0.4205 0.6038 0.7557 0.022 Uiso 1 1 calc R . .
 
 
 
#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_distance
    _geom_bond_site_symmetry_2
    _geom_bond_publ_flag
I1 C27 2.091(3) . ?
C3 C18 1.393(4) . ?
C3 C6 1.398(4) . ?
C3 H3 0.95 . ?
O4 N19 1.212(4) . ?
O5 C14 1.263(3) . ?
C6 C20 1.396(4) . ?
C6 C14 1.507(4) . ?
O8 C25 1.314(4) . ?
O8 H8 0.74(5) . ?
C9 C20 1.381(4) . ?
C9 C26 1.385(4) . ?
C9 N19 1.473(4) . ?
N10 C28 1.340(4) . ?
N10 C23 1.341(4) . ?
N10 H10 0.889(19) . ?
O11 N19 1.222(3) . ?
O13 C25 1.208(4) . ?
C14 O16 1.240(4) . ?
C18 C26 1.394(4) . ?
C18 C25 1.498(4) . ?
C20 H20 0.95 . ?
C23 C444 1.387(5) . ?
C23 H23 0.95 . ?
C26 H26 0.95 . ?
C27 C28 1.382(4) . ?
C27 C333 1.391(4) . ?
C28 H28 0.95 . ?
C444 C333 1.381(4) . ?
C444 H444 0.95 . ?
C333 H333 0.95 . ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C18 C3 C6 120.9(3) . . ?
C18 C3 H3 119.5 . . ?
C6 C3 H3 119.5 . . ?
C20 C6 C3 119.2(3) . . ?
C20 C6 C14 119.5(3) . . ?
C3 C6 C14 121.3(3) . . ?
C25 O8 H8 110(4) . . ?
C20 C9 C26 123.0(3) . . ?
C20 C9 N19 118.5(3) . . ?
C26 C9 N19 118.4(3) . . ?
C28 N10 C23 121.9(3) . . ?
C28 N10 H10 118(3) . . ?
C23 N10 H10 120(3) . . ?
O16 C14 O5 124.5(3) . . ?
O16 C14 C6 117.5(3) . . ?
O5 C14 C6 118.0(3) . . ?
C3 C18 C26 120.0(3) . . ?
C3 C18 C25 122.0(3) . . ?
C26 C18 C25 118.1(3) . . ?
O4 N19 O11 122.7(3) . . ?
O4 N19 C9 119.3(2) . . ?
O11 N19 C9 118.0(3) . . ?
C9 C20 C6 118.8(3) . . ?
C9 C20 H20 120.6 . . ?
C6 C20 H20 120.6 . . ?
N10 C23 C444 120.0(3) . . ?
N10 C23 H23 120 . . ?
C444 C23 H23 120 . . ?
O13 C25 O8 125.1(3) . . ?
O13 C25 C18 123.0(3) . . ?
O8 C25 C18 111.9(3) . . ?
C9 C26 C18 118.1(3) . . ?
C9 C26 H26 120.9 . . ?
C18 C26 H26 120.9 . . ?
C28 C27 C333 119.0(3) . . ?
C28 C27 I1 118.0(2) . . ?
C333 C27 I1 122.9(2) . . ?
N10 C28 C27 120.2(3) . . ?
N10 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C333 C444 C23 119.2(3) . . ?
C333 C444 H444 120.4 . . ?
C23 C444 H444 120.4 . . ?
C444 C333 C27 119.6(3) . . ?
C444 C333 H333 120.2 . . ?
C27 C333 H333 120.2 . . ?
 
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C18 C3 C6 C20 -0.4(4) . . . . ?
C18 C3 C6 C14 179.4(3) . . . . ?
C20 C6 C14 O16 -12.7(4) . . . . ?
C3 C6 C14 O16 167.5(3) . . . . ?
C20 C6 C14 O5 167.4(3) . . . . ?
C3 C6 C14 O5 -12.4(4) . . . . ?
C6 C3 C18 C26 -0.4(4) . . . . ?
C6 C3 C18 C25 179.7(3) . . . . ?
C20 C9 N19 O4 173.0(3) . . . . ?
C26 C9 N19 O4 -5.2(4) . . . . ?
C20 C9 N19 O11 -5.0(4) . . . . ?
C26 C9 N19 O11 176.9(3) . . . . ?
C26 C9 C20 C6 0.0(5) . . . . ?
N19 C9 C20 C6 -178.1(3) . . . . ?
C3 C6 C20 C9 0.6(4) . . . . ?
C14 C6 C20 C9 -179.2(3) . . . . ?
C28 N10 C23 C444 1.6(4) . . . . ?
C3 C18 C25 O13 175.6(3) . . . . ?
C26 C18 C25 O13 -4.2(5) . . . . ?
C3 C18 C25 O8 -4.0(4) . . . . ?
C26 C18 C25 O8 176.1(3) . . . . ?
C20 C9 C26 C18 -0.8(5) . . . . ?
N19 C9 C26 C18 177.3(3) . . . . ?
C3 C18 C26 C9 1.0(4) . . . . ?
C25 C18 C26 C9 -179.2(3) . . . . ?
C23 N10 C28 C27 -0.6(4) . . . . ?
C333 C27 C28 N10 -0.9(4) . . . . ?
I1 C27 C28 N10 -179.0(2) . . . . ?
N10 C23 C444 C333 -1.0(5) . . . . ?
C23 C444 C333 C27 -0.6(5) . . . . ?
C28 C27 C333 C444 1.5(4) . . . . ?
I1 C27 C333 C444 179.4(2) . . . . ?

# END of CIF
