

data_global
_publ_contact_author_email       florence.mongin@univ-rennes1.fr
_publ_contact_author_name        'Florence Mongin'


#\#CIF_1.1

#  CIF produced by WinGX routine CIF_UPDATE
#  Created on 2011-11-04 at 11:00:48
#  Using CIFtbx version 2.6.2 16 Jun 1998

#  Dictionary name : cif_core.dic
#  Dictionary vers : 2.3
#  Request file    : d:\program files\wingx\files\archive.dat
#  CIF files read  : job struct


data_2e

_audit_creation_date                    2011-11-04T11:00:48-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
_audit_conform_dict_name                cif_core.dic
_audit_conform_dict_version             2.3
_audit_conform_dict_location            ftp://ftp.iucr.org/pub/cif_core.dic
_publ_requested_category                FO

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C14 H10 Br1 N1'
_chemical_formula_sum                   'C14 H10 Br1 N1'
_chemical_formula_weight                272.14
_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'
_symmetry_Int_Tables_number             14
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                          9.7442(7)
_cell_length_b                          13.1654(12)
_cell_length_c                          17.8252(17)
_cell_angle_alpha                       90
_cell_angle_beta                        93.934(4)
_cell_angle_gamma                       90
_cell_volume                            2281.3(3)
_cell_formula_units_Z                   8
_cell_measurement_temperature           150(2)
_cell_measurement_reflns_used           1511
_cell_measurement_theta_min             3.3
_cell_measurement_theta_max             23.11
_cell_measurement_wavelength            0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description              prism
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.27
_exptl_crystal_size_mid                 0.22
_exptl_crystal_size_min                 0.11
_exptl_crystal_density_diffrn           1.585
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    1088
_exptl_special_details
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.572
_exptl_absorpt_correction_type                              multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.529
_exptl_absorpt_correction_T_max  0.675


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type         'APEXII, Bruker-AXS'
_diffrn_measurement_method              'CCD rotation images, thin slices'
_diffrn_detector                        'CCD plate'
_diffrn_ambient_temperature             150(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_radiation_probe                 x-ray
_diffrn_reflns_av_R_equivalents         0.0505
_diffrn_reflns_av_unetI/netI            0.0551
_diffrn_reflns_number                   17943
_diffrn_reflns_limit_h_min              -12
_diffrn_reflns_limit_h_max              10
_diffrn_reflns_limit_k_min              -17
_diffrn_reflns_limit_k_max              17
_diffrn_reflns_limit_l_min              -20
_diffrn_reflns_limit_l_max              23
_diffrn_reflns_theta_min                3.09
_diffrn_reflns_theta_max                27.51
_diffrn_reflns_theta_full               27.51
_diffrn_measured_fraction_theta_full
                                        0.996
_diffrn_measured_fraction_theta_max
                                        0.996
_reflns_number_total                    5231
_reflns_number_gt                       3568
_reflns_threshold_expression            >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection              'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement              'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction               'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution           'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material          
;
           WinGX publication routines (Farrugia, 1999),
           CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
#                   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 > 2sigma(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)+(0.0842P)²+14.6186P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
_refine_ls_hydrogen_treatment           constr
_refine_ls_extinction_method            none
_refine_ls_number_reflns                5231
_refine_ls_number_parameters            289
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.1171
_refine_ls_R_factor_gt                  0.0822
_refine_ls_wR_factor_ref                0.2264
_refine_ls_wR_factor_gt                 0.2092
_refine_ls_goodness_of_fit_ref          1.102
_refine_ls_restrained_S_all             1.102
_refine_ls_shift/su_max                 0.027
_refine_ls_shift/su_mean                0.003
_refine_diff_density_max                4.222
_refine_diff_density_min                -1.519
_refine_diff_density_rms                0.137


#----------------------------------------------------------------------------#
#                   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'

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
Br1  Br -0.06945(9)   0.93329(6)   0.12345(5)   0.0503(3)   Uani 1 1 d    .  . . 
C1   C  -0.1071(7)    0.7919(5)    0.1320(4)    0.0348(15)  Uani 1 1 d    .  . . 
C2   C   0.0001(7)    0.7256(6)    0.1511(4)    0.0359(15)  Uani 1 1 d    .  . . 
H2   H   0.0913       0.7504       0.1601       0.043       Uiso 1 1 calc R  . . 
C3   C  -0.0269(7)    0.6233(6)    0.1570(4)    0.0333(15)  Uani 1 1 d    .  . . 
H3   H   0.0458       0.5772       0.1701       0.04        Uiso 1 1 calc R  . . 
C4   C  -0.1602(6)    0.5875(5)    0.1440(3)    0.0285(13)  Uani 1 1 d    .  . . 
C5   C  -0.2676(7)    0.6556(6)    0.1256(4)    0.0347(15)  Uani 1 1 d    .  . . 
H5   H  -0.3589       0.6311       0.1165       0.042       Uiso 1 1 calc R  . . 
C6   C  -0.2413(8)    0.7583(6)    0.1207(4)    0.0421(17)  Uani 1 1 d    .  . . 
H6   H  -0.3141       0.8051       0.1098       0.05        Uiso 1 1 calc R  . . 
N7   N  -0.1898(6)    0.4828(5)    0.1502(3)    0.0324(12)  Uani 1 1 d    .  . . 
C8   C  -0.3029(7)    0.4436(6)    0.1854(4)    0.0424(18)  Uani 1 1 d    .  . . 
H8   H  -0.3662       0.4828       0.2114       0.051       Uiso 1 1 calc R  . . 
C9   C  -0.3080(8)    0.3422(6)    0.1766(4)    0.0433(18)  Uani 1 1 d    .  . . 
H9   H  -0.3746       0.298        0.1955       0.052       Uiso 1 1 calc R  . . 
C10  C  -0.1964(7)    0.3127(6)    0.1342(4)    0.0370(16)  Uani 1 1 d    .  . . 
C11  C  -0.1517(9)    0.2187(6)    0.1045(5)    0.0468(19)  Uani 1 1 d    .  . . 
H11  H  -0.1998       0.1577       0.1137       0.056       Uiso 1 1 calc R  . . 
C12  C  -0.0405(8)    0.2170(6)    0.0632(5)    0.0459(18)  Uani 1 1 d    .  . . 
H12  H  -0.0101       0.1543       0.0438       0.055       Uiso 1 1 calc R  . . 
C13  C   0.0305(8)    0.3066(6)    0.0484(4)    0.0394(17)  Uani 1 1 d    .  . . 
H13  H   0.1083       0.3035       0.0192       0.047       Uiso 1 1 calc R  . . 
C14  C  -0.0103(7)    0.3997(6)    0.0757(4)    0.0357(15)  Uani 1 1 d    .  . . 
H14  H   0.0373       0.4605       0.0651       0.043       Uiso 1 1 calc R  . . 
C15  C  -0.1233(7)    0.4008(5)    0.1189(3)    0.0292(14)  Uani 1 1 d    .  . . 
Br2  Br  0.06772(10)  0.67962(6)   0.43636(6)   0.0576(3)   Uani 1 1 d    .  . . 
C21  C   0.0841(7)    0.5436(5)    0.4017(4)    0.0318(14)  Uani 1 1 d    .  . . 
C22  C   0.1791(7)    0.4811(5)    0.4395(4)    0.0324(14)  Uani 1 1 d    .  . . 
H22  H   0.2326       0.5047       0.4826       0.039       Uiso 1 1 calc R  . . 
C23  C   0.1945(8)    0.3832(6)    0.4130(4)    0.0388(16)  Uani 1 1 d    .  . . 
H23  H   0.2596       0.3387       0.4379       0.047       Uiso 1 1 calc R  . . 
C24  C   0.1144(7)    0.3497(5)    0.3497(4)    0.0336(15)  Uani 1 1 d    .  . . 
C25  C   0.0180(7)    0.4134(6)    0.3148(4)    0.0366(16)  Uani 1 1 d    .  . . 
H25  H  -0.0386       0.3898       0.2729       0.044       Uiso 1 1 calc R  . . 
C26  C   0.0032(7)    0.5109(6)    0.3405(4)    0.0398(17)  Uani 1 1 d    .  . . 
H26  H  -0.0625       0.5553       0.316        0.048       Uiso 1 1 calc R  . . 
N27  N   0.1307(6)    0.2511(4)    0.3197(3)    0.0353(13)  Uani 1 1 d    .  . . 
C28  C   0.1336(8)    0.2275(7)    0.2431(4)    0.0446(18)  Uani 1 1 d    .  . . 
H28  H   0.1245       0.2757       0.2034       0.053       Uiso 1 1 calc R  . . 
C29  C   0.1510(8)    0.1275(7)    0.2337(5)    0.049(2)    Uani 1 1 d    .  . . 
H29  H   0.1589       0.0931       0.1873       0.059       Uiso 1 1 calc R  . . 
C30  C   0.1554(7)    0.0824(6)    0.3065(5)    0.0462(19)  Uani 1 1 d    .  . . 
C31  C   0.1667(8)   -0.0203(6)    0.3325(6)    0.052(2)    Uani 1 1 d    .  . . 
H31  H   0.1759      -0.0749       0.2984       0.062       Uiso 1 1 calc R  . . 
C32  C   0.1637(9)   -0.0372(7)    0.4082(6)    0.060(3)    Uani 1 1 d    .  . . 
H32  H   0.17        -0.1049       0.4266       0.071       Uiso 1 1 calc R  . . 
C33  C   0.1513(8)    0.0449(6)    0.4606(5)    0.051(2)    Uani 1 1 d    .  . . 
H33  H   0.1496       0.0301       0.5127       0.061       Uiso 1 1 calc R  . . 
C34  C   0.1419(8)    0.1434(6)    0.4373(5)    0.0459(19)  Uani 1 1 d    .  . . 
H34  H   0.1339       0.198        0.4717       0.055       Uiso 1 1 calc R  . . 
C35  C   0.1448(6)    0.1597(5)    0.3586(4)    0.0329(15)  Uani 1 1 d    .  . . 





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
Br1  C1   1.906(7)    .           ?           
C1   C6   1.381(11)   .           ?           
C1   C2   1.387(10)   .           ?           
C2   C3   1.378(10)   .           ?           
C2   H2   0.95        .           ?           
C3   C4   1.386(9)    .           ?           
C3   H3   0.95        .           ?           
C4   C5   1.400(9)    .           ?           
C4   N7   1.414(9)    .           ?           
C5   C6   1.379(11)   .           ?           
C5   H5   0.95        .           ?           
C6   H6   0.95        .           ?           
N7   C15  1.395(9)    .           ?           
N7   C8   1.403(9)    .           ?           
C8   C9   1.345(11)   .           ?           
C8   H8   0.95        .           ?           
C9   C10  1.421(11)   .           ?           
C9   H9   0.95        .           ?           
C10  C15  1.397(10)   .           ?           
C10  C11  1.425(11)   .           ?           
C11  C12  1.352(12)   .           ?           
C11  H11  0.95        .           ?           
C12  C13  1.401(11)   .           ?           
C12  H12  0.95        .           ?           
C13  C14  1.387(10)   .           ?           
C13  H13  0.95        .           ?           
C14  C15  1.387(10)   .           ?           
C14  H14  0.95        .           ?           
Br2  C21  1.905(6)    .           ?           
C21  C26  1.371(10)   .           ?           
C21  C22  1.379(10)   .           ?           
C22  C23  1.385(10)   .           ?           
C22  H22  0.95        .           ?           
C23  C24  1.400(10)   .           ?           
C23  H23  0.95        .           ?           
C24  C25  1.375(10)   .           ?           
C24  N27  1.417(9)    .           ?           
C25  C26  1.374(10)   .           ?           
C25  H25  0.95        .           ?           
C26  H26  0.95        .           ?           
N27  C35  1.391(9)    .           ?           
N27  C28  1.402(9)    .           ?           
C28  C29  1.339(12)   .           ?           
C28  H28  0.95        .           ?           
C29  C30  1.426(12)   .           ?           
C29  H29  0.95        .           ?           
C30  C35  1.386(10)   .           ?           
C30  C31  1.431(11)   .           ?           
C31  C32  1.369(14)   .           ?           
C31  H31  0.95        .           ?           
C32  C33  1.439(13)   .           ?           
C32  H32  0.95        .           ?           
C33  C34  1.363(11)   .           ?           
C33  H33  0.95        .           ?           
C34  C35  1.423(11)   .           ?           
C34  H34  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
C6   C1   C2   121.6(7)     .       .       ?       
C6   C1   Br1  119.1(5)     .       .       ?       
C2   C1   Br1  119.2(6)     .       .       ?       
C3   C2   C1   119.3(7)     .       .       ?       
C3   C2   H2   120.4        .       .       ?       
C1   C2   H2   120.4        .       .       ?       
C2   C3   C4   120.1(6)     .       .       ?       
C2   C3   H3   119.9        .       .       ?       
C4   C3   H3   119.9        .       .       ?       
C3   C4   C5   119.9(7)     .       .       ?       
C3   C4   N7   120.8(6)     .       .       ?       
C5   C4   N7   119.3(6)     .       .       ?       
C6   C5   C4   120.2(7)     .       .       ?       
C6   C5   H5   119.9        .       .       ?       
C4   C5   H5   119.9        .       .       ?       
C5   C6   C1   118.9(7)     .       .       ?       
C5   C6   H6   120.6        .       .       ?       
C1   C6   H6   120.6        .       .       ?       
C15  N7   C8   107.2(6)     .       .       ?       
C15  N7   C4   128.3(5)     .       .       ?       
C8   N7   C4   124.3(6)     .       .       ?       
C9   C8   N7   109.7(7)     .       .       ?       
C9   C8   H8   125.2        .       .       ?       
N7   C8   H8   125.2        .       .       ?       
C8   C9   C10  108.0(7)     .       .       ?       
C8   C9   H9   126          .       .       ?       
C10  C9   H9   126          .       .       ?       
C15  C10  C9   107.2(7)     .       .       ?       
C15  C10  C11  118.4(7)     .       .       ?       
C9   C10  C11  134.4(7)     .       .       ?       
C12  C11  C10  119.6(8)     .       .       ?       
C12  C11  H11  120.2        .       .       ?       
C10  C11  H11  120.2        .       .       ?       
C11  C12  C13  120.9(8)     .       .       ?       
C11  C12  H12  119.6        .       .       ?       
C13  C12  H12  119.6        .       .       ?       
C14  C13  C12  121.4(7)     .       .       ?       
C14  C13  H13  119.3        .       .       ?       
C12  C13  H13  119.3        .       .       ?       
C15  C14  C13  117.5(7)     .       .       ?       
C15  C14  H14  121.3        .       .       ?       
C13  C14  H14  121.3        .       .       ?       
C14  C15  N7   129.7(6)     .       .       ?       
C14  C15  C10  122.3(7)     .       .       ?       
N7   C15  C10  107.9(6)     .       .       ?       
C26  C21  C22  122.2(6)     .       .       ?       
C26  C21  Br2  119.8(5)     .       .       ?       
C22  C21  Br2  118.0(5)     .       .       ?       
C21  C22  C23  118.2(6)     .       .       ?       
C21  C22  H22  120.9        .       .       ?       
C23  C22  H22  120.9        .       .       ?       
C22  C23  C24  120.1(6)     .       .       ?       
C22  C23  H23  120          .       .       ?       
C24  C23  H23  120          .       .       ?       
C25  C24  C23  119.9(6)     .       .       ?       
C25  C24  N27  118.6(6)     .       .       ?       
C23  C24  N27  121.5(6)     .       .       ?       
C26  C25  C24  120.2(7)     .       .       ?       
C26  C25  H25  119.9        .       .       ?       
C24  C25  H25  119.9        .       .       ?       
C21  C26  C25  119.4(7)     .       .       ?       
C21  C26  H26  120.3        .       .       ?       
C25  C26  H26  120.3        .       .       ?       
C35  N27  C28  106.6(6)     .       .       ?       
C35  N27  C24  127.9(6)     .       .       ?       
C28  N27  C24  125.5(6)     .       .       ?       
C29  C28  N27  110.5(8)     .       .       ?       
C29  C28  H28  124.7        .       .       ?       
N27  C28  H28  124.7        .       .       ?       
C28  C29  C30  106.9(7)     .       .       ?       
C28  C29  H29  126.5        .       .       ?       
C30  C29  H29  126.5        .       .       ?       
C35  C30  C29  107.8(7)     .       .       ?       
C35  C30  C31  119.0(8)     .       .       ?       
C29  C30  C31  133.3(8)     .       .       ?       
C32  C31  C30  117.8(8)     .       .       ?       
C32  C31  H31  121.1        .       .       ?       
C30  C31  H31  121.1        .       .       ?       
C31  C32  C33  121.7(8)     .       .       ?       
C31  C32  H32  119.1        .       .       ?       
C33  C32  H32  119.1        .       .       ?       
C34  C33  C32  121.6(9)     .       .       ?       
C34  C33  H33  119.2        .       .       ?       
C32  C33  H33  119.2        .       .       ?       
C33  C34  C35  116.0(8)     .       .       ?       
C33  C34  H34  122          .       .       ?       
C35  C34  H34  122          .       .       ?       
C30  C35  N27  108.1(7)     .       .       ?       
C30  C35  C34  123.9(7)     .       .       ?       
N27  C35  C34  127.9(7)     .       .       ?       


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
C6   C1   C2   C3      1.9(11)    .       .       .       .       ?       
Br1  C1   C2   C3   -179.8(5)     .       .       .       .       ?       
C1   C2   C3   C4      0.0(10)    .       .       .       .       ?       
C2   C3   C4   C5     -0.8(10)    .       .       .       .       ?       
C2   C3   C4   N7   -179.7(6)     .       .       .       .       ?       
C3   C4   C5   C6     -0.2(10)    .       .       .       .       ?       
N7   C4   C5   C6    178.7(6)     .       .       .       .       ?       
C4   C5   C6   C1      1.9(11)    .       .       .       .       ?       
C2   C1   C6   C5     -2.8(11)    .       .       .       .       ?       
Br1  C1   C6   C5    178.8(5)     .       .       .       .       ?       
C3   C4   N7   C15   -48.9(9)     .       .       .       .       ?       
C5   C4   N7   C15   132.2(7)     .       .       .       .       ?       
C3   C4   N7   C8    136.7(7)     .       .       .       .       ?       
C5   C4   N7   C8    -42.2(9)     .       .       .       .       ?       
C15  N7   C8   C9     -0.2(8)     .       .       .       .       ?       
C4   N7   C8   C9    175.2(6)     .       .       .       .       ?       
N7   C8   C9   C10    -0.4(9)     .       .       .       .       ?       
C8   C9   C10  C15     0.8(9)     .       .       .       .       ?       
C8   C9   C10  C11  -176.6(8)     .       .       .       .       ?       
C15  C10  C11  C12     0.4(11)    .       .       .       .       ?       
C9   C10  C11  C12   177.6(8)     .       .       .       .       ?       
C10  C11  C12  C13    -0.7(12)    .       .       .       .       ?       
C11  C12  C13  C14     0.1(12)    .       .       .       .       ?       
C12  C13  C14  C15     0.8(10)    .       .       .       .       ?       
C13  C14  C15  N7   -176.7(6)     .       .       .       .       ?       
C13  C14  C15  C10    -1.1(10)    .       .       .       .       ?       
C8   N7   C15  C14   176.9(7)     .       .       .       .       ?       
C4   N7   C15  C14     1.7(11)    .       .       .       .       ?       
C8   N7   C15  C10     0.7(7)     .       .       .       .       ?       
C4   N7   C15  C10  -174.5(6)     .       .       .       .       ?       
C9   C10  C15  C14  -177.4(6)     .       .       .       .       ?       
C11  C10  C15  C14     0.5(10)    .       .       .       .       ?       
C9   C10  C15  N7     -0.9(7)     .       .       .       .       ?       
C11  C10  C15  N7    177.0(6)     .       .       .       .       ?       
C26  C21  C22  C23     1.6(11)    .       .       .       .       ?       
Br2  C21  C22  C23  -177.9(5)     .       .       .       .       ?       
C21  C22  C23  C24    -0.3(11)    .       .       .       .       ?       
C22  C23  C24  C25    -1.6(11)    .       .       .       .       ?       
C22  C23  C24  N27   177.9(6)     .       .       .       .       ?       
C23  C24  C25  C26     2.2(11)    .       .       .       .       ?       
N27  C24  C25  C26  -177.3(6)     .       .       .       .       ?       
C22  C21  C26  C25    -1.0(11)    .       .       .       .       ?       
Br2  C21  C26  C25   178.5(5)     .       .       .       .       ?       
C24  C25  C26  C21    -0.9(11)    .       .       .       .       ?       
C25  C24  N27  C35  -136.1(7)     .       .       .       .       ?       
C23  C24  N27  C35    44.4(10)    .       .       .       .       ?       
C25  C24  N27  C28    42.8(10)    .       .       .       .       ?       
C23  C24  N27  C28  -136.7(8)     .       .       .       .       ?       
C35  N27  C28  C29    -1.1(8)     .       .       .       .       ?       
C24  N27  C28  C29   179.8(7)     .       .       .       .       ?       
N27  C28  C29  C30     1.9(9)     .       .       .       .       ?       
C28  C29  C30  C35    -2.0(9)     .       .       .       .       ?       
C28  C29  C30  C31   177.4(8)     .       .       .       .       ?       
C35  C30  C31  C32     1.3(11)    .       .       .       .       ?       
C29  C30  C31  C32  -178.1(8)     .       .       .       .       ?       
C30  C31  C32  C33    -0.7(12)    .       .       .       .       ?       
C31  C32  C33  C34     0.0(13)    .       .       .       .       ?       
C32  C33  C34  C35     0.1(11)    .       .       .       .       ?       
C29  C30  C35  N27     1.4(8)     .       .       .       .       ?       
C31  C30  C35  N27  -178.1(6)     .       .       .       .       ?       
C29  C30  C35  C34   178.3(7)     .       .       .       .       ?       
C31  C30  C35  C34    -1.2(11)    .       .       .       .       ?       
C28  N27  C35  C30    -0.2(7)     .       .       .       .       ?       
C24  N27  C35  C30   178.9(7)     .       .       .       .       ?       
C28  N27  C35  C34  -177.0(7)     .       .       .       .       ?       
C24  N27  C35  C34     2.1(11)    .       .       .       .       ?       
C33  C34  C35  C30     0.5(11)    .       .       .       .       ?       
C33  C34  C35  N27   176.8(7)     .       .       .       .       ?       


data_4c

_audit_creation_date                    2015-01-19T15:23:56-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
_audit_conform_dict_name                cif_core.dic
_audit_conform_dict_version             2.3
_audit_conform_dict_location            ftp://ftp.iucr.org/pub/cif_core.dic
_publ_requested_category                FO

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C14 H10 I N'
_chemical_formula_sum                   'C14 H10 I N'
_chemical_formula_weight                319.13
_chemical_compound_source               'synthesis as described'
_chemical_absolute_configuration        ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M          'C c'
_symmetry_space_group_name_Hall         'C -2yc'
_symmetry_Int_Tables_number             9
loop_
    _symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                          7.0800(3)
_cell_length_b                          20.6660(10)
_cell_length_c                          8.2442(5)
_cell_angle_alpha                       90
_cell_angle_beta                        100.632(2)
_cell_angle_gamma                       90
_cell_volume                            1185.54(10)
_cell_formula_units_Z                   4
_cell_measurement_temperature           150(2)
_cell_measurement_reflns_used           3333
_cell_measurement_theta_min             3.09
_cell_measurement_theta_max             27.43
_cell_measurement_wavelength            0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description              prism
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.39
_exptl_crystal_size_mid                 0.36
_exptl_crystal_size_min                 0.26
_exptl_crystal_density_diffrn           1.788
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    616
_exptl_special_details
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu                           2.671
_exptl_absorpt_correction_type                       multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min                         0.380
_exptl_absorpt_correction_T_max                         0.499


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type         'APEXII, Bruker-AXS'
_diffrn_measurement_method              'CCD rotation images, thin slices'
_diffrn_detector                        'CCD plate'
_diffrn_ambient_temperature             150(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_radiation_probe                 x-ray
_diffrn_reflns_av_R_equivalents         0.0279
_diffrn_reflns_av_unetI/netI            0.0347
_diffrn_reflns_number                   5134
_diffrn_reflns_limit_h_min              -9
_diffrn_reflns_limit_h_max              6
_diffrn_reflns_limit_k_min              -26
_diffrn_reflns_limit_k_max              26
_diffrn_reflns_limit_l_min              -10
_diffrn_reflns_limit_l_max              10
_diffrn_reflns_theta_min                3.09
_diffrn_reflns_theta_max                27.48
_diffrn_reflns_theta_full               27.48
_diffrn_measured_fraction_theta_full
                                        0.997
_diffrn_measured_fraction_theta_max
                                        0.997
_reflns_number_total                    2183
_reflns_number_gt                       2139
_reflns_threshold_expression            >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection              'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement              'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction               'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution           'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
          WinGX publication routines (Farrugia, 2012),
          CRYSCALc (T. Roisnel, local program, 2014)
;

#----------------------------------------------------------------------------#
#                   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 > 2sigma(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)+(0.0290P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
_refine_ls_hydrogen_treatment           constr
_refine_ls_extinction_method            none
_refine_ls_number_reflns                2183
_refine_ls_number_parameters            145
_refine_ls_number_restraints            2
_refine_ls_R_factor_all                 0.0238
_refine_ls_R_factor_gt                  0.0233
_refine_ls_wR_factor_ref                0.0566
_refine_ls_wR_factor_gt                 0.0563
_refine_ls_goodness_of_fit_ref          1.1
_refine_ls_restrained_S_all             1.099
_refine_ls_shift/su_max                 0
_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          -0.03(3)
_refine_diff_density_max                0.318
_refine_diff_density_min                -0.601
_refine_diff_density_rms                0.096

# End of res file

# End of hkl file
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   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'
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   0.21584(8)   0.122139(9)  0.20037(8)   0.02277(8)  Uani 1 1 d    .  . .
C1   C  -0.0095(5)    0.10092(18)  0.0112(5)    0.0151(7)   Uani 1 1 d    .  . .
C2   C  -0.0040(5)    0.06330(18) -0.1229(5)    0.0181(8)   Uani 1 1 d    .  . .
H2   H   0.1052       0.0412      -0.147        0.022       Uiso 1 1 calc R  . .
C3   C  -0.1942(5)    0.06317(17) -0.2217(5)    0.0149(7)   Uani 1 1 d    .  . .
C4   C  -0.2783(6)    0.03179(18) -0.3677(5)    0.0200(8)   Uani 1 1 d    .  . .
H4   H  -0.2035       0.0052      -0.4254       0.024       Uiso 1 1 calc R  . .
C5   C  -0.4724(7)    0.0403(2)   -0.4261(5)    0.0238(9)   Uani 1 1 d    .  . .
H5   H  -0.5318       0.0187      -0.5241       0.029       Uiso 1 1 calc R  . .
C6   C  -0.5841(6)    0.08066(19) -0.3423(5)    0.0215(8)   Uani 1 1 d    .  . .
H6   H  -0.7173       0.0857      -0.3851       0.026       Uiso 1 1 calc R  . .
C7   C  -0.5039(6)    0.11280(18) -0.1997(6)    0.0201(9)   Uani 1 1 d    .  . .
H7   H  -0.5786       0.1403      -0.1441       0.024       Uiso 1 1 calc R  . .
C8   C  -0.3084(5)    0.10322(17) -0.1408(5)    0.0144(7)   Uani 1 1 d    .  . .
N9   N  -0.1929(5)    0.12709(13)  0.0031(4)    0.0150(7)   Uani 1 1 d    .  . .
C10  C  -0.2577(5)    0.1678(2)    0.1196(6)    0.0157(9)   Uani 1 1 d    .  . .
C11  C  -0.2569(6)    0.1454(2)    0.2819(6)    0.0179(9)   Uani 1 1 d    .  . .
H11  H  -0.2097       0.1033       0.313        0.021       Uiso 1 1 calc R  . .
C12  C  -0.3237(6)    0.1837(2)    0.3945(6)    0.0245(9)   Uani 1 1 d    .  . .
H12  H  -0.3204       0.1686       0.5039       0.029       Uiso 1 1 calc R  . .
C13  C  -0.3962(6)    0.2448(2)    0.3482(6)    0.0283(10)  Uani 1 1 d    .  . .
H13  H  -0.4427       0.2713       0.4263       0.034       Uiso 1 1 calc R  . .
C14  C  -0.4012(5)    0.2672(2)    0.1898(6)    0.0269(10)  Uani 1 1 d    .  . .
H14  H  -0.4523       0.3088       0.1584       0.032       Uiso 1 1 calc R  . .
C15  C  -0.3302(5)    0.22809(18)  0.0754(5)    0.0207(8)   Uani 1 1 d    .  . .
H15  H  -0.3325       0.2435      -0.0335       0.025       Uiso 1 1 calc R  . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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   C1   2.062(4)    .           ?
C1   C2   1.358(6)    .           ?
C1   N9   1.397(5)    .           ?
C2   C3   1.439(5)    .           ?
C2   H2   0.95        .           ?
C3   C4   1.400(5)    .           ?
C3   C8   1.408(5)    .           ?
C4   C5   1.381(6)    .           ?
C4   H4   0.95        .           ?
C5   C6   1.415(6)    .           ?
C5   H5   0.95        .           ?
C6   C7   1.378(6)    .           ?
C6   H6   0.95        .           ?
C7   C8   1.394(5)    .           ?
C7   H7   0.95        .           ?
C8   N9   1.400(5)    .           ?
N9   C10  1.415(5)    .           ?
C10  C15  1.371(6)    .           ?
C10  C11  1.415(6)    .           ?
C11  C12  1.370(6)    .           ?
C11  H11  0.95        .           ?
C12  C13  1.388(6)    .           ?
C12  H12  0.95        .           ?
C13  C14  1.380(7)    .           ?
C13  H13  0.95        .           ?
C14  C15  1.404(6)    .           ?
C14  H14  0.95        .           ?
C15  H15  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
C2   C1   N9   110.4(3)     .       .       ?
C2   C1   I1   127.1(3)     .       .       ?
N9   C1   I1   122.5(3)     .       .       ?
C1   C2   C3   107.3(3)     .       .       ?
C1   C2   H2   126.3        .       .       ?
C3   C2   H2   126.3        .       .       ?
C4   C3   C8   119.3(3)     .       .       ?
C4   C3   C2   133.9(4)     .       .       ?
C8   C3   C2   106.8(3)     .       .       ?
C5   C4   C3   118.6(4)     .       .       ?
C5   C4   H4   120.7        .       .       ?
C3   C4   H4   120.7        .       .       ?
C4   C5   C6   121.0(4)     .       .       ?
C4   C5   H5   119.5        .       .       ?
C6   C5   H5   119.5        .       .       ?
C7   C6   C5   121.4(4)     .       .       ?
C7   C6   H6   119.3        .       .       ?
C5   C6   H6   119.3        .       .       ?
C6   C7   C8   117.1(4)     .       .       ?
C6   C7   H7   121.5        .       .       ?
C8   C7   H7   121.5        .       .       ?
C7   C8   N9   129.2(4)     .       .       ?
C7   C8   C3   122.6(3)     .       .       ?
N9   C8   C3   108.2(3)     .       .       ?
C1   N9   C8   107.3(3)     .       .       ?
C1   N9   C10  127.8(3)     .       .       ?
C8   N9   C10  124.9(3)     .       .       ?
C15  C10  C11  119.0(4)     .       .       ?
C15  C10  N9   120.8(4)     .       .       ?
C11  C10  N9   120.1(3)     .       .       ?
C12  C11  C10  120.7(4)     .       .       ?
C12  C11  H11  119.7        .       .       ?
C10  C11  H11  119.7        .       .       ?
C11  C12  C13  119.7(4)     .       .       ?
C11  C12  H12  120.2        .       .       ?
C13  C12  H12  120.2        .       .       ?
C14  C13  C12  120.6(4)     .       .       ?
C14  C13  H13  119.7        .       .       ?
C12  C13  H13  119.7        .       .       ?
C13  C14  C15  119.5(4)     .       .       ?
C13  C14  H14  120.3        .       .       ?
C15  C14  H14  120.3        .       .       ?
C10  C15  C14  120.5(4)     .       .       ?
C10  C15  H15  119.7        .       .       ?
C14  C15  H15  119.7        .       .       ?


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
N9   C1   C2   C3     -1.7(4)     .       .       .       .       ?
I1   C1   C2   C3   -179.3(3)     .       .       .       .       ?
C1   C2   C3   C4   -177.0(4)     .       .       .       .       ?
C1   C2   C3   C8      1.1(4)     .       .       .       .       ?
C8   C3   C4   C5     -1.2(6)     .       .       .       .       ?
C2   C3   C4   C5    176.7(4)     .       .       .       .       ?
C3   C4   C5   C6      1.0(6)     .       .       .       .       ?
C4   C5   C6   C7      0.0(6)     .       .       .       .       ?
C5   C6   C7   C8     -0.7(6)     .       .       .       .       ?
C6   C7   C8   N9   -176.9(4)     .       .       .       .       ?
C6   C7   C8   C3      0.6(6)     .       .       .       .       ?
C4   C3   C8   C7      0.4(6)     .       .       .       .       ?
C2   C3   C8   C7   -178.0(4)     .       .       .       .       ?
C4   C3   C8   N9    178.3(3)     .       .       .       .       ?
C2   C3   C8   N9     -0.1(4)     .       .       .       .       ?
C2   C1   N9   C8      1.6(4)     .       .       .       .       ?
I1   C1   N9   C8    179.3(2)     .       .       .       .       ?
C2   C1   N9   C10   179.0(4)     .       .       .       .       ?
I1   C1   N9   C10    -3.3(5)     .       .       .       .       ?
C7   C8   N9   C1    176.8(4)     .       .       .       .       ?
C3   C8   N9   C1     -0.9(4)     .       .       .       .       ?
C7   C8   N9   C10    -0.6(6)     .       .       .       .       ?
C3   C8   N9   C10  -178.3(4)     .       .       .       .       ?
C1   N9   C10  C15   121.1(4)     .       .       .       .       ?
C8   N9   C10  C15   -62.0(5)     .       .       .       .       ?
C1   N9   C10  C11   -62.1(6)     .       .       .       .       ?
C8   N9   C10  C11   114.8(4)     .       .       .       .       ?
C15  C10  C11  C12    -1.4(6)     .       .       .       .       ?
N9   C10  C11  C12  -178.4(4)     .       .       .       .       ?
C10  C11  C12  C13     1.2(6)     .       .       .       .       ?
C11  C12  C13  C14    -0.1(6)     .       .       .       .       ?
C12  C13  C14  C15    -0.7(6)     .       .       .       .       ?
C11  C10  C15  C14     0.6(5)     .       .       .       .       ?
N9   C10  C15  C14   177.5(4)     .       .       .       .       ?
C13  C14  C15  C10     0.5(5)     .       .       .       .       ?


data_3d

_audit_creation_date                    2015-01-19T16:19:36-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
_audit_conform_dict_name                cif_core.dic
_audit_conform_dict_version             2.3
_audit_conform_dict_location            ftp://ftp.iucr.org/pub/cif_core.dic
_publ_requested_category                FO

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C11 H10 I N O'
_chemical_formula_sum                   'C11 H10 I N O'
_chemical_formula_weight                299.1
_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'
_symmetry_Int_Tables_number             14
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                          9.9461(4)
_cell_length_b                          6.9825(3)
_cell_length_c                          15.2049(8)
_cell_angle_alpha                       90
_cell_angle_beta                        92.314(2)
_cell_angle_gamma                       90
_cell_volume                            1055.10(8)
_cell_formula_units_Z                   4
_cell_measurement_temperature           150(2)
_cell_measurement_reflns_used           4169
_cell_measurement_theta_min             2.68
_cell_measurement_theta_max             27.42
_cell_measurement_wavelength            0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description              block
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.45
_exptl_crystal_size_mid                 0.37
_exptl_crystal_size_min                 0.14
_exptl_crystal_density_diffrn           1.883
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    576
_exptl_special_details
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu                           3.001
_exptl_absorpt_correction_type                       multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min                         0.474
_exptl_absorpt_correction_T_max                         0.657


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type         'APEXII, Bruker-AXS'
_diffrn_measurement_method              'CCD rotation images, thin slices'
_diffrn_detector                        'CCD plate'
_diffrn_ambient_temperature             150(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_radiation_probe                 x-ray
_diffrn_reflns_av_R_equivalents         0.0366
_diffrn_reflns_av_unetI/netI            0.0325
_diffrn_reflns_number                   9219
_diffrn_reflns_limit_h_min              -8
_diffrn_reflns_limit_h_max              12
_diffrn_reflns_limit_k_min              -9
_diffrn_reflns_limit_k_max              8
_diffrn_reflns_limit_l_min              -19
_diffrn_reflns_limit_l_max              19
_diffrn_reflns_theta_min                3.21
_diffrn_reflns_theta_max                27.48
_diffrn_reflns_theta_full               27.48
_diffrn_measured_fraction_theta_full
                                        0.999
_diffrn_measured_fraction_theta_max
                                        0.999
_reflns_number_total                    2409
_reflns_number_gt                       2149
_reflns_threshold_expression            >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection              'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement              'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction               'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution           'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
          WinGX publication routines (Farrugia, 2012),
          CRYSCALc (T. Roisnel, local program, 2014)
;

#----------------------------------------------------------------------------#
#                   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 > 2sigma(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)+(0.0216P)²+0.1733P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
_refine_ls_hydrogen_treatment           constr
_refine_ls_extinction_method            none
_refine_ls_number_reflns                2409
_refine_ls_number_parameters            128
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.0292
_refine_ls_R_factor_gt                  0.0253
_refine_ls_wR_factor_ref                0.0567
_refine_ls_wR_factor_gt                 0.0548
_refine_ls_goodness_of_fit_ref          1.083
_refine_ls_restrained_S_all             1.083
_refine_ls_shift/su_max                 0.003
_refine_ls_shift/su_mean                0.001
_refine_diff_density_max                0.692
_refine_diff_density_min                -0.603
_refine_diff_density_rms                0.092

# End of res file

# End of hkl file
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   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   0.329898(16) 0.26502(2)   0.025896(12) 0.02892(8)  Uani 1 1 d    .  . .
C1   C   0.0348(3)    0.7312(4)    0.0980(2)    0.0328(7)   Uani 1 1 d    .  . .
H1A  H   0.0109       0.7237       0.1598       0.049       Uiso 1 1 calc R  . .
H1B  H  -0.0441       0.6999       0.06         0.049       Uiso 1 1 calc R  . .
H1C  H   0.0653       0.8613       0.0849       0.049       Uiso 1 1 calc R  . .
O2   O   0.14107(15)  0.5974(2)    0.08228(11)  0.0235(4)   Uani 1 1 d    .  . .
C3   C   0.2572(2)    0.6173(3)    0.13225(16)  0.0190(5)   Uani 1 1 d    .  . .
C4   C   0.2803(2)    0.7584(3)    0.19549(18)  0.0224(6)   Uani 1 1 d    .  . .
H4   H   0.2137       0.8536       0.2037       0.027       Uiso 1 1 calc R  . .
C5   C   0.3983(3)    0.7626(3)    0.24669(19)  0.0232(6)   Uani 1 1 d    .  . .
H5   H   0.4127       0.8613       0.289        0.028       Uiso 1 1 calc R  . .
C6   C   0.4964(2)    0.6223(3)    0.23640(15)  0.0168(5)   Uani 1 1 d    .  . .
C7   C   0.4758(2)    0.4832(3)    0.17213(15)  0.0185(5)   Uani 1 1 d    .  . .
H7   H   0.5429       0.3888       0.1637       0.022       Uiso 1 1 calc R  . .
C8   C   0.3585(2)    0.4810(3)    0.12034(15)  0.0181(5)   Uani 1 1 d    .  . .
N9   N   0.61473(18)  0.6198(3)    0.29203(13)  0.0186(4)   Uani 1 1 d    .  . .
C10  C   0.6282(2)    0.6985(3)    0.37527(17)  0.0222(5)   Uani 1 1 d    .  . .
H10  H   0.5605       0.7666       0.4046       0.027       Uiso 1 1 calc R  . .
C11  C   0.7549(2)    0.6618(3)    0.40811(17)  0.0230(5)   Uani 1 1 d    .  . .
H11  H   0.7916       0.7001       0.464        0.028       Uiso 1 1 calc R  . .
C12  C   0.8220(2)    0.5561(3)    0.34356(17)  0.0226(5)   Uani 1 1 d    .  . .
H12  H   0.9119       0.5102       0.3485       0.027       Uiso 1 1 calc R  . .
C13  C   0.7341(2)    0.5322(3)    0.27295(17)  0.0218(5)   Uani 1 1 d    .  . .
H13  H   0.7522       0.4666       0.22         0.026       Uiso 1 1 calc R  . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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   C8   2.094(2)    .           ?
C1   O2   1.438(3)    .           ?
C1   H1A  0.98        .           ?
C1   H1B  0.98        .           ?
C1   H1C  0.98        .           ?
O2   C3   1.364(3)    .           ?
C3   C4   1.389(3)    .           ?
C3   C8   1.403(3)    .           ?
C4   C5   1.383(4)    .           ?
C4   H4   0.95        .           ?
C5   C6   1.396(3)    .           ?
C5   H5   0.95        .           ?
C6   C7   1.388(3)    .           ?
C6   N9   1.421(3)    .           ?
C7   C8   1.382(3)    .           ?
C7   H7   0.95        .           ?
N9   C13  1.377(3)    .           ?
N9   C10  1.381(3)    .           ?
C10  C11  1.361(3)    .           ?
C10  H10  0.95        .           ?
C11  C12  1.416(3)    .           ?
C11  H11  0.95        .           ?
C12  C13  1.367(3)    .           ?
C12  H12  0.95        .           ?
C13  H13  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
O2   C1   H1A  109.5        .       .       ?
O2   C1   H1B  109.5        .       .       ?
H1A  C1   H1B  109.5        .       .       ?
O2   C1   H1C  109.5        .       .       ?
H1A  C1   H1C  109.5        .       .       ?
H1B  C1   H1C  109.5        .       .       ?
C3   O2   C1   116.90(19)   .       .       ?
O2   C3   C4   124.8(2)     .       .       ?
O2   C3   C8   117.1(2)     .       .       ?
C4   C3   C8   118.1(2)     .       .       ?
C5   C4   C3   121.2(2)     .       .       ?
C5   C4   H4   119.4        .       .       ?
C3   C4   H4   119.4        .       .       ?
C4   C5   C6   120.2(2)     .       .       ?
C4   C5   H5   119.9        .       .       ?
C6   C5   H5   119.9        .       .       ?
C7   C6   C5   119.1(2)     .       .       ?
C7   C6   N9   120.37(19)   .       .       ?
C5   C6   N9   120.5(2)     .       .       ?
C8   C7   C6   120.4(2)     .       .       ?
C8   C7   H7   119.8        .       .       ?
C6   C7   H7   119.8        .       .       ?
C7   C8   C3   120.9(2)     .       .       ?
C7   C8   I1   119.14(16)   .       .       ?
C3   C8   I1   119.94(17)   .       .       ?
C13  N9   C10  108.5(2)     .       .       ?
C13  N9   C6   125.5(2)     .       .       ?
C10  N9   C6   126.00(19)   .       .       ?
C11  C10  N9   108.4(2)     .       .       ?
C11  C10  H10  125.8        .       .       ?
N9   C10  H10  125.8        .       .       ?
C10  C11  C12  107.4(2)     .       .       ?
C10  C11  H11  126.3        .       .       ?
C12  C11  H11  126.3        .       .       ?
C13  C12  C11  107.7(2)     .       .       ?
C13  C12  H12  126.2        .       .       ?
C11  C12  H12  126.2        .       .       ?
C12  C13  N9   108.0(2)     .       .       ?
C12  C13  H13  126          .       .       ?
N9   C13  H13  126          .       .       ?


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
C1   O2   C3   C4     -1.1(3)     .       .       .       .       ?
C1   O2   C3   C8    176.8(2)     .       .       .       .       ?
O2   C3   C4   C5    176.5(2)     .       .       .       .       ?
C8   C3   C4   C5     -1.3(4)     .       .       .       .       ?
C3   C4   C5   C6     -0.9(4)     .       .       .       .       ?
C4   C5   C6   C7      2.3(4)     .       .       .       .       ?
C4   C5   C6   N9   -176.6(2)     .       .       .       .       ?
C5   C6   C7   C8     -1.4(3)     .       .       .       .       ?
N9   C6   C7   C8    177.4(2)     .       .       .       .       ?
C6   C7   C8   C3     -0.8(3)     .       .       .       .       ?
C6   C7   C8   I1   -178.76(16)   .       .       .       .       ?
O2   C3   C8   C7   -175.85(19)   .       .       .       .       ?
C4   C3   C8   C7      2.1(3)     .       .       .       .       ?
O2   C3   C8   I1      2.1(3)     .       .       .       .       ?
C4   C3   C8   I1   -179.90(17)   .       .       .       .       ?
C7   C6   N9   C13    22.5(3)     .       .       .       .       ?
C5   C6   N9   C13  -158.6(2)     .       .       .       .       ?
C7   C6   N9   C10  -155.0(2)     .       .       .       .       ?
C5   C6   N9   C10    23.8(3)     .       .       .       .       ?
C13  N9   C10  C11     0.3(3)     .       .       .       .       ?
C6   N9   C10  C11   178.3(2)     .       .       .       .       ?
N9   C10  C11  C12    -0.4(3)     .       .       .       .       ?
C10  C11  C12  C13     0.3(3)     .       .       .       .       ?
C11  C12  C13  N9      0.0(3)     .       .       .       .       ?
C10  N9   C13  C12    -0.2(3)     .       .       .       .       ?
C6   N9   C13  C12  -178.11(19)   .       .       .       .       ?


data_3e

_audit_creation_date                    2015-03-09T17:28:31-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
_audit_conform_dict_name                cif_core.dic
_audit_conform_dict_version             2.3
_audit_conform_dict_location            ftp://ftp.iucr.org/pub/cif_core.dic
_publ_requested_category                FO

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C10 H7 Br I N'
_chemical_formula_sum                   'C10 H7 Br I N'
_chemical_formula_weight                347.98
_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'
_symmetry_Int_Tables_number             14
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                          10.0665(5)
_cell_length_b                          5.9895(4)
_cell_length_c                          17.5155(10)
_cell_angle_alpha                       90
_cell_angle_beta                        103.942(3)
_cell_angle_gamma                       90
_cell_volume                            1024.96(10)
_cell_formula_units_Z                   4
_cell_measurement_temperature           150(2)
_cell_measurement_reflns_used           2681
_cell_measurement_theta_min             3.61
_cell_measurement_theta_max             27.25
_cell_measurement_wavelength            0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description              prism
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.54
_exptl_crystal_size_mid                 0.45
_exptl_crystal_size_min                 0.3
_exptl_crystal_density_diffrn           2.255
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    648
_exptl_special_details
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu                           6.974
_exptl_absorpt_correction_type                       multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min                         0.065
_exptl_absorpt_correction_T_max                         0.123


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type         'APEXII, Bruker-AXS'
_diffrn_measurement_method              'CCD rotation images, thin slices'
_diffrn_detector                        'CCD plate'
_diffrn_ambient_temperature             150(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_radiation_probe                 x-ray
_diffrn_reflns_av_R_equivalents         0.046
_diffrn_reflns_av_unetI/netI            0.0426
_diffrn_reflns_number                   8842
_diffrn_reflns_limit_h_min              -13
_diffrn_reflns_limit_h_max              12
_diffrn_reflns_limit_k_min              -7
_diffrn_reflns_limit_k_max              7
_diffrn_reflns_limit_l_min              -22
_diffrn_reflns_limit_l_max              22
_diffrn_reflns_theta_min                3.61
_diffrn_reflns_theta_max                27.47
_diffrn_reflns_theta_full               27.47
_diffrn_measured_fraction_theta_full
                                        0.997
_diffrn_measured_fraction_theta_max
                                        0.997
_reflns_number_total                    2335
_reflns_number_gt                       1971
_reflns_threshold_expression            >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection              'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement              'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction               'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution           'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
          WinGX publication routines (Farrugia, 2012),
          CRYSCALc (T. Roisnel, local program, 2014)
;

#----------------------------------------------------------------------------#
#                   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 > 2sigma(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)+(0.0431P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
_refine_ls_hydrogen_treatment           constr
_refine_ls_extinction_method            none
_refine_ls_number_reflns                2335
_refine_ls_number_parameters            118
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.041
_refine_ls_R_factor_gt                  0.032
_refine_ls_wR_factor_ref                0.0828
_refine_ls_wR_factor_gt                 0.0789
_refine_ls_goodness_of_fit_ref          1.034
_refine_ls_restrained_S_all             1.034
_refine_ls_shift/su_max                 0.001
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.713
_refine_diff_density_min                -1.235
_refine_diff_density_rms                0.152

# End of res file
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   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
C1   C   0.3195(5)    0.2731(7)    0.1247(3)    0.0257(10)  Uani 1 1 d    .  . .
H1   H   0.3652       0.1504       0.1081       0.031       Uiso 1 1 calc R  . .
C2   C   0.1940(4)    0.3507(8)    0.0876(3)    0.0277(10)  Uani 1 1 d    .  . .
H2   H   0.1371       0.2943       0.0402       0.033       Uiso 1 1 calc R  . .
C3   C   0.1640(4)    0.5300(8)    0.1324(3)    0.0262(10)  Uani 1 1 d    .  . .
H3   H   0.0819       0.615        0.1213       0.031       Uiso 1 1 calc R  . .
C4   C   0.2725(4)    0.5600(8)    0.1939(2)    0.0259(10)  Uani 1 1 d    .  . .
H4   H   0.2802       0.6724       0.233        0.031       Uiso 1 1 calc R  . .
N5   N   0.3700(3)    0.4022(5)    0.19091(18)  0.0156(7)   Uani 1 1 d    .  . .
C6   C   0.4953(4)    0.3675(7)    0.2469(2)    0.0141(8)   Uani 1 1 d    .  . .
C7   C   0.5763(4)    0.1826(7)    0.2423(3)    0.0198(9)   Uani 1 1 d    .  . .
H7   H   0.5471       0.0771       0.2011       0.024       Uiso 1 1 calc R  . .
C8   C   0.6976(4)    0.1514(7)    0.2964(2)    0.0204(9)   Uani 1 1 d    .  . .
H8   H   0.7523       0.0248       0.2923       0.025       Uiso 1 1 calc R  . .
C9   C   0.7422(4)    0.3028(6)    0.3577(2)    0.0157(8)   Uani 1 1 d    .  . .
C10  C   0.6603(4)    0.4834(6)    0.3646(2)    0.0157(8)   Uani 1 1 d    .  . .
C11  C   0.5374(4)    0.5167(6)    0.3091(2)    0.0162(8)   Uani 1 1 d    .  . .
H11  H   0.4819       0.6419       0.3135       0.019       Uiso 1 1 calc R  . .
Br1  Br  0.91712(4)   0.25708(7)   0.42674(3)   0.02315(13) Uani 1 1 d    .  . .
I1   I   0.71001(3)   0.70912(5)   0.458540(17) 0.02595(12) Uani 1 1 d    .  . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
C1   C2   1.356(6)    .           ?
C1   N5   1.384(5)    .           ?
C1   H1   0.95        .           ?
C2   C3   1.405(6)    .           ?
C2   H2   0.95        .           ?
C3   C4   1.349(6)    .           ?
C3   H3   0.95        .           ?
C4   N5   1.372(5)    .           ?
C4   H4   0.95        .           ?
N5   C6   1.414(5)    .           ?
C6   C7   1.389(6)    .           ?
C6   C11  1.393(5)    .           ?
C7   C8   1.367(6)    .           ?
C7   H7   0.95        .           ?
C8   C9   1.394(6)    .           ?
C8   H8   0.95        .           ?
C9   C10  1.384(5)    .           ?
C9   Br1  1.900(4)    .           ?
C10  C11  1.392(5)    .           ?
C10  I1   2.094(4)    .           ?
C11  H11  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
C2   C1   N5   108.8(4)     .       .       ?
C2   C1   H1   125.6        .       .       ?
N5   C1   H1   125.6        .       .       ?
C1   C2   C3   107.2(4)     .       .       ?
C1   C2   H2   126.4        .       .       ?
C3   C2   H2   126.4        .       .       ?
C4   C3   C2   107.8(4)     .       .       ?
C4   C3   H3   126.1        .       .       ?
C2   C3   H3   126.1        .       .       ?
C3   C4   N5   109.1(4)     .       .       ?
C3   C4   H4   125.5        .       .       ?
N5   C4   H4   125.5        .       .       ?
C4   N5   C1   107.1(3)     .       .       ?
C4   N5   C6   127.0(3)     .       .       ?
C1   N5   C6   125.8(3)     .       .       ?
C7   C6   C11  119.0(4)     .       .       ?
C7   C6   N5   121.0(4)     .       .       ?
C11  C6   N5   120.0(3)     .       .       ?
C8   C7   C6   120.5(4)     .       .       ?
C8   C7   H7   119.8        .       .       ?
C6   C7   H7   119.8        .       .       ?
C7   C8   C9   120.9(4)     .       .       ?
C7   C8   H8   119.6        .       .       ?
C9   C8   H8   119.6        .       .       ?
C10  C9   C8   119.2(4)     .       .       ?
C10  C9   Br1  122.5(3)     .       .       ?
C8   C9   Br1  118.3(3)     .       .       ?
C9   C10  C11  119.9(4)     .       .       ?
C9   C10  I1   122.6(3)     .       .       ?
C11  C10  I1   117.5(3)     .       .       ?
C10  C11  C6   120.4(4)     .       .       ?
C10  C11  H11  119.8        .       .       ?
C6   C11  H11  119.8        .       .       ?


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
N5   C1   C2   C3     -1.1(5)     .       .       .       .       ?
C1   C2   C3   C4      1.5(5)     .       .       .       .       ?
C2   C3   C4   N5     -1.3(5)     .       .       .       .       ?
C3   C4   N5   C1      0.7(5)     .       .       .       .       ?
C3   C4   N5   C6   -175.9(4)     .       .       .       .       ?
C2   C1   N5   C4      0.3(5)     .       .       .       .       ?
C2   C1   N5   C6    177.0(4)     .       .       .       .       ?
C4   N5   C6   C7    171.1(4)     .       .       .       .       ?
C1   N5   C6   C7     -4.9(6)     .       .       .       .       ?
C4   N5   C6   C11    -7.1(6)     .       .       .       .       ?
C1   N5   C6   C11   176.9(4)     .       .       .       .       ?
C11  C6   C7   C8     -2.1(6)     .       .       .       .       ?
N5   C6   C7   C8    179.6(3)     .       .       .       .       ?
C6   C7   C8   C9      0.5(6)     .       .       .       .       ?
C7   C8   C9   C10     1.8(6)     .       .       .       .       ?
C7   C8   C9   Br1  -176.3(3)     .       .       .       .       ?
C8   C9   C10  C11    -2.5(6)     .       .       .       .       ?
Br1  C9   C10  C11   175.5(3)     .       .       .       .       ?
C8   C9   C10  I1    175.6(3)     .       .       .       .       ?
Br1  C9   C10  I1     -6.4(5)     .       .       .       .       ?
C9   C10  C11  C6      0.9(6)     .       .       .       .       ?
I1   C10  C11  C6   -177.3(3)     .       .       .       .       ?
C7   C6   C11  C10     1.4(6)     .       .       .       .       ?
N5   C6   C11  C10   179.7(3)     .       .       .       .       ?


data_5d

_audit_creation_date                    2014-10-28T15:05:45-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
_audit_conform_dict_name                cif_core.dic
_audit_conform_dict_version             2.3
_audit_conform_dict_location            ftp://ftp.iucr.org/pub/cif_core.dic
_publ_requested_category                FO

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety                'C14 H13 N3 O'
_chemical_formula_sum                   'C14 H13 N3 O'
_chemical_formula_weight                239.27
_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'
_symmetry_Int_Tables_number             14
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                          11.4222(6)
_cell_length_b                          5.4888(3)
_cell_length_c                          19.7338(12)
_cell_angle_alpha                       90
_cell_angle_beta                        100.562(2)
_cell_angle_gamma                       90
_cell_volume                            1216.23(12)
_cell_formula_units_Z                   4
_cell_measurement_temperature           150(2)
_cell_measurement_reflns_used           3354
_cell_measurement_theta_min             3.33
_cell_measurement_theta_max             27.37
_cell_measurement_wavelength            0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description              prism
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.57
_exptl_crystal_size_mid                 0.44
_exptl_crystal_size_min                 0.3
_exptl_crystal_density_diffrn           1.307
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    504
_exptl_special_details
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type                              multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_T_max  0.975


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type         'APEXII, Bruker-AXS'
_diffrn_measurement_method              'CCD rotation images, thin slices'
_diffrn_detector                        'CCD plate'
_diffrn_ambient_temperature             150(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_radiation_probe                 x-ray
_diffrn_reflns_av_R_equivalents         0.034
_diffrn_reflns_av_unetI/netI            0.03
_diffrn_reflns_number                   10156
_diffrn_reflns_limit_h_min              -12
_diffrn_reflns_limit_h_max              14
_diffrn_reflns_limit_k_min              -7
_diffrn_reflns_limit_k_max              6
_diffrn_reflns_limit_l_min              -25
_diffrn_reflns_limit_l_max              25
_diffrn_reflns_theta_min                3.33
_diffrn_reflns_theta_max                27.48
_diffrn_reflns_theta_full               27.48
_diffrn_measured_fraction_theta_full
                                        0.998
_diffrn_measured_fraction_theta_max
                                        0.998
_reflns_number_total                    2777
_reflns_number_gt                       2281
_reflns_threshold_expression            >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection              'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement              'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction               'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution           'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
          WinGX publication routines (Farrugia, 2012),
          CRYSCALc (T. Roisnel, local program, 2014)
;

#----------------------------------------------------------------------------#
#                   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 > 2sigma(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)+(0.0542P)²+0.2677P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
_refine_ls_hydrogen_treatment           constr
_refine_ls_extinction_method            none
_refine_ls_number_reflns                2777
_refine_ls_number_parameters            164
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.0505
_refine_ls_R_factor_gt                  0.0404
_refine_ls_wR_factor_ref                0.1081
_refine_ls_wR_factor_gt                 0.101
_refine_ls_goodness_of_fit_ref          1.031
_refine_ls_restrained_S_all             1.031
_refine_ls_shift/su_max                 0.002
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.177
_refine_diff_density_min                -0.279
_refine_diff_density_rms                0.047

# End of res file
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   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'


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
C1   C   0.44878(11) -0.1182(2)    0.70950(6)   0.0274(3)   Uani 1 1 d    .  . .
H1   H   0.4407      -0.256        0.6799       0.033       Uiso 1 1 calc R  . .
C2   C   0.38098(12) -0.0693(3)    0.75799(7)   0.0324(3)   Uani 1 1 d    .  . .
H2   H   0.3175      -0.1662       0.7682       0.039       Uiso 1 1 calc R  . .
C3   C   0.42263(12)  0.1525(3)    0.79028(7)   0.0323(3)   Uani 1 1 d    .  . .
H3   H   0.3923       0.2316       0.8262       0.039       Uiso 1 1 calc R  . .
C4   C   0.51414(12)  0.2321(2)    0.76046(6)   0.0279(3)   Uani 1 1 d    .  . .
H4   H   0.5587       0.3772       0.772        0.034       Uiso 1 1 calc R  . .
N5   N   0.53097(9)   0.06617(18)  0.71071(5)   0.0233(2)   Uani 1 1 d    .  . .
C6   C   0.61830(11)  0.0807(2)    0.66793(6)   0.0223(3)   Uani 1 1 d    .  . .
C7   C   0.71766(11)  0.2289(2)    0.68629(6)   0.0254(3)   Uani 1 1 d    .  . .
H7   H   0.7256       0.3256       0.7268       0.031       Uiso 1 1 calc R  . .
C8   C   0.80552(11)  0.2375(2)    0.64605(6)   0.0268(3)   Uani 1 1 d    .  . .
H8   H   0.8722       0.342        0.6588       0.032       Uiso 1 1 calc R  . .
C9   C   0.79634(11)  0.0939(2)    0.58729(6)   0.0248(3)   Uani 1 1 d    .  . .
O10  O   0.88016(8)   0.08312(18)  0.54635(5)   0.0339(2)   Uani 1 1 d    .  . .
C11  C   0.97973(15)  0.2436(3)    0.56298(9)   0.0520(5)   Uani 1 1 d    .  . .
H11A H   0.9515       0.4123       0.5624       0.078       Uiso 1 1 calc R  . .
H11B H   1.0317       0.2243       0.529        0.078       Uiso 1 1 calc R  . .
H11C H   1.0243       0.2042       0.609        0.078       Uiso 1 1 calc R  . .
C12  C   0.69471(11) -0.0522(2)    0.56828(6)   0.0221(3)   Uani 1 1 d    .  . .
C13  C   0.60592(11) -0.0567(2)    0.60756(6)   0.0224(3)   Uani 1 1 d    .  . .
H13  H   0.5367      -0.1531       0.5934       0.027       Uiso 1 1 calc R  . .
N14  N   0.68208(9)  -0.20133(18)  0.50809(5)   0.0230(2)   Uani 1 1 d    .  . .
C15  C   0.70124(11) -0.1364(2)    0.44324(6)   0.0269(3)   Uani 1 1 d    .  . .
H15  H   0.7284       0.0163       0.4296       0.032       Uiso 1 1 calc R  . .
C16  C   0.67320(11) -0.3362(2)    0.40346(6)   0.0279(3)   Uani 1 1 d    .  . .
H16  H   0.6775      -0.3451       0.3559       0.033       Uiso 1 1 calc R  . .
N17  N   0.63744(10) -0.5255(2)    0.44096(5)   0.0319(3)   Uani 1 1 d    .  . .
C18  C   0.64359(12) -0.4369(2)    0.50325(6)   0.0286(3)   Uani 1 1 d    .  . .
H18  H   0.6235      -0.5265       0.5407       0.034       Uiso 1 1 calc R  . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
C1   C2   1.3634(18)  .           ?
C1   N5   1.3775(16)  .           ?
C1   H1   0.95        .           ?
C2   C3   1.415(2)    .           ?
C2   H2   0.95        .           ?
C3   C4   1.3621(19)  .           ?
C3   H3   0.95        .           ?
C4   N5   1.3784(16)  .           ?
C4   H4   0.95        .           ?
N5   C6   1.4222(15)  .           ?
C6   C7   1.3895(17)  .           ?
C6   C13  1.3949(16)  .           ?
C7   C8   1.3900(18)  .           ?
C7   H7   0.95        .           ?
C8   C9   1.3898(17)  .           ?
C8   H8   0.95        .           ?
C9   O10  1.3625(15)  .           ?
C9   C12  1.4043(17)  .           ?
O10  C11  1.4283(17)  .           ?
C11  H11A 0.98        .           ?
C11  H11B 0.98        .           ?
C11  H11C 0.98        .           ?
C12  C13  1.3849(17)  .           ?
C12  N14  1.4279(14)  .           ?
C13  H13  0.95        .           ?
N14  C18  1.3633(16)  .           ?
N14  C15  1.3839(15)  .           ?
C15  C16  1.3524(17)  .           ?
C15  H15  0.95        .           ?
C16  N17  1.3800(17)  .           ?
C16  H16  0.95        .           ?
N17  C18  1.3119(16)  .           ?
C18  H18  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
C2   C1   N5   108.44(11)   .       .       ?
C2   C1   H1   125.8        .       .       ?
N5   C1   H1   125.8        .       .       ?
C1   C2   C3   107.34(12)   .       .       ?
C1   C2   H2   126.3        .       .       ?
C3   C2   H2   126.3        .       .       ?
C4   C3   C2   107.62(12)   .       .       ?
C4   C3   H3   126.2        .       .       ?
C2   C3   H3   126.2        .       .       ?
C3   C4   N5   108.30(12)   .       .       ?
C3   C4   H4   125.8        .       .       ?
N5   C4   H4   125.9        .       .       ?
C1   N5   C4   108.31(10)   .       .       ?
C1   N5   C6   125.51(10)   .       .       ?
C4   N5   C6   126.19(10)   .       .       ?
C7   C6   C13  119.30(11)   .       .       ?
C7   C6   N5   120.41(10)   .       .       ?
C13  C6   N5   120.29(11)   .       .       ?
C6   C7   C8   120.76(11)   .       .       ?
C6   C7   H7   119.6        .       .       ?
C8   C7   H7   119.6        .       .       ?
C9   C8   C7   120.37(11)   .       .       ?
C9   C8   H8   119.8        .       .       ?
C7   C8   H8   119.8        .       .       ?
O10  C9   C8   124.45(11)   .       .       ?
O10  C9   C12  116.94(11)   .       .       ?
C8   C9   C12  118.62(11)   .       .       ?
C9   O10  C11  116.97(10)   .       .       ?
O10  C11  H11A 109.5        .       .       ?
O10  C11  H11B 109.5        .       .       ?
H11A C11  H11B 109.5        .       .       ?
O10  C11  H11C 109.5        .       .       ?
H11A C11  H11C 109.5        .       .       ?
H11B C11  H11C 109.5        .       .       ?
C13  C12  C9   120.99(11)   .       .       ?
C13  C12  N14  118.86(11)   .       .       ?
C9   C12  N14  120.14(11)   .       .       ?
C12  C13  C6   119.89(11)   .       .       ?
C12  C13  H13  120.1        .       .       ?
C6   C13  H13  120.1        .       .       ?
C18  N14  C15  106.44(10)   .       .       ?
C18  N14  C12  125.73(10)   .       .       ?
C15  N14  C12  127.79(10)   .       .       ?
C16  C15  N14  105.50(11)   .       .       ?
C16  C15  H15  127.2        .       .       ?
N14  C15  H15  127.2        .       .       ?
C15  C16  N17  111.16(11)   .       .       ?
C15  C16  H16  124.4        .       .       ?
N17  C16  H16  124.4        .       .       ?
C18  N17  C16  104.66(11)   .       .       ?
N17  C18  N14  112.23(11)   .       .       ?
N17  C18  H18  123.9        .       .       ?
N14  C18  H18  123.9        .       .       ?


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
N5   C1   C2   C3     -0.03(15)   .       .       .       .       ?
C1   C2   C3   C4      0.13(15)   .       .       .       .       ?
C2   C3   C4   N5     -0.18(15)   .       .       .       .       ?
C2   C1   N5   C4     -0.08(14)   .       .       .       .       ?
C2   C1   N5   C6    179.66(11)   .       .       .       .       ?
C3   C4   N5   C1      0.16(14)   .       .       .       .       ?
C3   C4   N5   C6   -179.58(11)   .       .       .       .       ?
C1   N5   C6   C7   -160.60(11)   .       .       .       .       ?
C4   N5   C6   C7     19.09(18)   .       .       .       .       ?
C1   N5   C6   C13    18.47(17)   .       .       .       .       ?
C4   N5   C6   C13  -161.83(11)   .       .       .       .       ?
C13  C6   C7   C8     -1.40(18)   .       .       .       .       ?
N5   C6   C7   C8    177.68(11)   .       .       .       .       ?
C6   C7   C8   C9     -1.16(19)   .       .       .       .       ?
C7   C8   C9   O10  -177.29(11)   .       .       .       .       ?
C7   C8   C9   C12     2.28(18)   .       .       .       .       ?
C8   C9   O10  C11    -4.5(2)     .       .       .       .       ?
C12  C9   O10  C11   175.96(13)   .       .       .       .       ?
O10  C9   C12  C13   178.72(11)   .       .       .       .       ?
C8   C9   C12  C13    -0.88(18)   .       .       .       .       ?
O10  C9   C12  N14    -0.62(16)   .       .       .       .       ?
C8   C9   C12  N14   179.78(11)   .       .       .       .       ?
C9   C12  C13  C6     -1.67(17)   .       .       .       .       ?
N14  C12  C13  C6    177.68(10)   .       .       .       .       ?
C7   C6   C13  C12     2.80(17)   .       .       .       .       ?
N5   C6   C13  C12  -176.29(10)   .       .       .       .       ?
C13  C12  N14  C18   -43.07(17)   .       .       .       .       ?
C9   C12  N14  C18   136.28(13)   .       .       .       .       ?
C13  C12  N14  C15   134.19(12)   .       .       .       .       ?
C9   C12  N14  C15   -46.45(17)   .       .       .       .       ?
C18  N14  C15  C16     0.00(13)   .       .       .       .       ?
C12  N14  C15  C16  -177.68(11)   .       .       .       .       ?
N14  C15  C16  N17    -0.25(14)   .       .       .       .       ?
C15  C16  N17  C18     0.40(15)   .       .       .       .       ?
C16  N17  C18  N14    -0.40(15)   .       .       .       .       ?
C15  N14  C18  N17     0.26(15)   .       .       .       .       ?
C12  N14  C18  N17   178.00(11)   .       .       .       .       ?