
data_07035
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H16 F12 O4'
_chemical_formula_weight          476.27
 
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'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F'  'F'   0.0171   0.0103
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2/n
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y, z-1/2'
 
_cell_length_a                    10.243(4)
_cell_length_b                    5.633(2)
_cell_length_c                    15.676(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  94.912(5)
_cell_angle_gamma                 90.00
_cell_volume                      901.1(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        ireg.blok
_exptl_crystal_colour             colourless
_exptl_crystal_size_min           0.300
_exptl_crystal_size_mid           0.350
_exptl_crystal_size_max           0.440
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.755
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              480
_exptl_absorpt_coefficient_mu     0.204
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker P4'
_diffrn_measurement_method        'ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             8958
_diffrn_reflns_av_R_equivalents   0.0304
_diffrn_reflns_av_sigmaI/netI     0.0275
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          2.29
_diffrn_reflns_theta_max          28.34
_reflns_number_total              2251
_reflns_number_gt                 1746
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'Bruker XSCANS'
_computing_cell_refinement        'Bruker XSCANS'
_computing_data_reduction         'Bruker SHELXTL'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
 
_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)+(0.0427P)²+0.2237P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     riding
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2251
_refine_ls_number_parameters      137
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0493
_refine_ls_R_factor_gt            0.0349
_refine_ls_wR_factor_ref          0.0927
_refine_ls_wR_factor_gt           0.0847
_refine_ls_goodness_of_fit_ref    1.043
_refine_ls_restrained_S_all       1.043
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
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
O1 O 0.39258(8) 0.30256(16) 0.54692(6) 0.0244(2) Uani 1 1 d . . .
F6 F 0.34046(9) 0.65973(17) 0.66731(5) 0.0381(2) Uani 1 1 d . . .
O2 O 0.55543(9) 0.15532(17) 0.64171(6) 0.0279(2) Uani 1 1 d . . .
F1 F 0.25785(9) 0.3390(2) 0.38883(6) 0.0471(3) Uani 1 1 d . . .
F3 F 0.14677(9) 0.21290(17) 0.48888(6) 0.0409(2) Uani 1 1 d . . .
F5 F 0.18425(9) 0.40939(18) 0.64291(6) 0.0429(3) Uani 1 1 d . . .
F4 F 0.16534(10) 0.76291(19) 0.59149(6) 0.0493(3) Uani 1 1 d . . .
F2 F 0.11383(9) 0.56389(19) 0.43887(7) 0.0499(3) Uani 1 1 d . . .
C1 C 0.31316(12) 0.5031(2) 0.52657(8) 0.0230(3) Uani 1 1 d . . .
C4 C 0.24882(14) 0.5839(3) 0.60745(9) 0.0301(3) Uani 1 1 d . . .
C2 C 0.38080(13) 0.7192(2) 0.48998(8) 0.0241(3) Uani 1 1 d . . .
H2A H 0.3135 0.8292 0.4675 0.029 Uiso 1 1 calc R . .
H2B H 0.4316 0.7984 0.5367 0.029 Uiso 1 1 calc R . .
C5 C 0.52842(12) 0.3313(2) 0.58076(8) 0.0226(3) Uani 1 1 d . . .
H5A H 0.5441 0.4898 0.6053 0.027 Uiso 1 1 calc R . .
C3 C 0.20619(13) 0.4031(3) 0.46057(9) 0.0303(3) Uani 1 1 d . . .
C7 C 0.55884(16) 0.0172(3) 0.78504(9) 0.0389(4) Uani 1 1 d . . .
H7A H 0.5192 0.0323 0.8381 0.058 Uiso 1 1 calc R . .
H7B H 0.6510 0.0491 0.7945 0.058 Uiso 1 1 calc R . .
H7C H 0.5458 -0.1412 0.7633 0.058 Uiso 1 1 calc R . .
C6 C 0.49701(15) 0.1914(3) 0.72125(9) 0.0329(3) Uani 1 1 d . . .
H6A H 0.4031 0.1655 0.7132 0.039 Uiso 1 1 calc R . .
H6B H 0.5126 0.3525 0.7415 0.039 Uiso 1 1 calc R . .
 
 
_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
O1 C1 1.4125(16) . ?
O1 C5 1.4550(16) . ?
F6 C4 1.3392(17) . ?
O2 C5 1.3880(16) . ?
O2 C6 1.4429(17) . ?
F1 C3 1.3328(18) . ?
F3 C3 1.3270(17) . ?
F5 C4 1.3322(17) . ?
F4 C4 1.3320(17) . ?
F2 C3 1.3327(17) . ?
C1 C2 1.5359(18) . ?
C1 C4 1.5465(19) . ?
C1 C3 1.5473(19) . ?
C2 C5 1.5336(18) 3_666 ?
C5 C2 1.5336(18) 3_666 ?
C7 C6 1.502(2) . ?
 
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
C1 O1 C5 120.51(10) . . ?
C5 O2 C6 114.91(10) . . ?
O1 C1 C2 116.66(11) . . ?
O1 C1 C4 109.13(10) . . ?
C2 C1 C4 108.10(11) . . ?
O1 C1 C3 102.77(11) . . ?
C2 C1 C3 110.80(11) . . ?
C4 C1 C3 109.16(11) . . ?
F4 C4 F5 107.65(12) . . ?
F4 C4 F6 106.86(12) . . ?
F5 C4 F6 106.63(12) . . ?
F4 C4 C1 112.36(11) . . ?
F5 C4 C1 112.75(12) . . ?
F6 C4 C1 110.25(11) . . ?
C5 C2 C1 116.35(11) 3_666 . ?
O2 C5 O1 107.43(10) . . ?
O2 C5 C2 105.52(10) . 3_666 ?
O1 C5 C2 109.62(10) . 3_666 ?
F3 C3 F2 107.34(12) . . ?
F3 C3 F1 106.88(12) . . ?
F2 C3 F1 107.03(12) . . ?
F3 C3 C1 112.90(11) . . ?
F2 C3 C1 111.69(12) . . ?
F1 C3 C1 110.68(11) . . ?
O2 C6 C7 107.51(12) . . ?
 
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
C5 O1 C1 C2 35.40(16) . . . . ?
C5 O1 C1 C4 -87.42(13) . . . . ?
C5 O1 C1 C3 156.81(10) . . . . ?
O1 C1 C4 F4 -175.73(11) . . . . ?
C2 C1 C4 F4 56.47(15) . . . . ?
C3 C1 C4 F4 -64.13(16) . . . . ?
O1 C1 C4 F5 -53.86(15) . . . . ?
C2 C1 C4 F5 178.34(11) . . . . ?
C3 C1 C4 F5 57.74(15) . . . . ?
O1 C1 C4 F6 65.19(14) . . . . ?
C2 C1 C4 F6 -62.61(14) . . . . ?
C3 C1 C4 F6 176.79(11) . . . . ?
O1 C1 C2 C5 45.90(15) . . . 3_666 ?
C4 C1 C2 C5 169.24(11) . . . 3_666 ?
C3 C1 C2 C5 -71.18(14) . . . 3_666 ?
C6 O2 C5 O1 -73.22(14) . . . . ?
C6 O2 C5 C2 169.87(11) . . . 3_666 ?
C1 O1 C5 O2 142.43(11) . . . . ?
C1 O1 C5 C2 -103.38(12) . . . 3_666 ?
O1 C1 C3 F3 53.44(14) . . . . ?
C2 C1 C3 F3 178.76(11) . . . . ?
C4 C1 C3 F3 -62.31(15) . . . . ?
O1 C1 C3 F2 174.52(11) . . . . ?
C2 C1 C3 F2 -60.16(15) . . . . ?
C4 C1 C3 F2 58.78(15) . . . . ?
O1 C1 C3 F1 -66.32(14) . . . . ?
C2 C1 C3 F1 59.00(15) . . . . ?
C4 C1 C3 F1 177.93(11) . . . . ?
C5 O2 C6 C7 -167.99(12) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              28.34
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.337
_refine_diff_density_min   -0.261
_refine_diff_density_rms    0.046
#===END
 
data_08131 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C16 H20 F12 O4' 
_chemical_formula_weight          504.32 
  
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'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'F'  'F'   0.0171   0.0103 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_symmetry_cell_setting            Triclinic 
_symmetry_space_group_name_H-M    P-1 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
  
_cell_length_a                    5.564(2) 
_cell_length_b                    9.647(4) 
_cell_length_c                    9.926(4) 
_cell_angle_alpha                 100.015(6) 
_cell_angle_beta                  105.203(6) 
_cell_angle_gamma                 92.977(6) 
_cell_volume                      503.7(3) 
_cell_formula_units_Z             1 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     1074 
_cell_measurement_theta_min       2.74 
_cell_measurement_theta_max       22.10 
  
_exptl_crystal_description        oval.block 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_min           0.08 
_exptl_crystal_size_mid           0.08 
_exptl_crystal_size_max           0.15 
_exptl_crystal_density_meas       'not measured' 
_exptl_crystal_density_diffrn     1.663 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              256 
_exptl_absorpt_coefficient_mu     0.188 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             5386 
_diffrn_reflns_av_R_equivalents   0.0364 
_diffrn_reflns_av_sigmaI/netI     0.0621 
_diffrn_reflns_limit_h_min        -7 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -13 
_diffrn_reflns_limit_l_max        13 
_diffrn_reflns_theta_min          2.16 
_diffrn_reflns_theta_max          28.02 
_reflns_number_total              2404 
_reflns_number_gt                 1382 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_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)+(0.0607P)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     riding 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          2404 
_refine_ls_number_parameters      185 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1011 
_refine_ls_R_factor_gt            0.0501 
_refine_ls_wR_factor_ref          0.1263 
_refine_ls_wR_factor_gt           0.1057 
_refine_ls_goodness_of_fit_ref    0.965 
_refine_ls_restrained_S_all       0.965 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
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 
O1 O -0.1806(3) 0.87971(16) 0.06071(15) 0.0311(4) Uani 1 1 d . . . 
F1 F -0.0017(3) 1.07033(15) 0.30970(15) 0.0524(4) Uani 1 1 d . . . 
C1 C 0.0662(4) 0.8771(2) 0.1451(2) 0.0286(5) Uani 1 1 d . . . 
O2 O -0.4530(3) 0.80602(15) -0.16051(16) 0.0328(4) Uani 1 1 d . . . 
F2 F 0.2693(3) 0.93587(17) 0.39272(15) 0.0557(4) Uani 1 1 d . . . 
C2 C -0.2287(4) 0.8877(2) -0.0887(2) 0.0290(5) Uani 1 1 d . . . 
F3 F -0.1202(3) 0.86556(17) 0.33499(15) 0.0538(4) Uani 1 1 d . . . 
C3 C -0.2722(4) 1.0393(2) -0.1078(3) 0.0304(5) Uani 1 1 d . . . 
F4 F 0.3472(3) 0.70841(15) 0.21845(16) 0.0571(5) Uani 1 1 d . . . 
C4 C 0.0526(4) 0.9369(3) 0.2969(3) 0.0371(6) Uani 1 1 d . . . 
F5 F -0.0447(3) 0.63970(15) 0.16501(17) 0.0546(4) Uani 1 1 d . . . 
C5 C 0.1234(4) 0.7221(3) 0.1340(3) 0.0374(6) Uani 1 1 d . . . 
F6 F 0.1258(3) 0.66632(14) 0.00119(15) 0.0455(4) Uani 1 1 d . . . 
C6 C -0.4417(5) 0.6556(3) -0.1895(3) 0.0383(6) Uani 1 1 d . . . 
C7 C -0.6737(5) 0.5923(3) -0.3061(3) 0.0398(6) Uani 1 1 d . . . 
C8 C -0.6925(7) 0.6464(4) -0.4420(3) 0.0544(8) Uani 1 1 d . . . 
H3 H -0.302(4) 1.097(2) -0.022(3) 0.032(6) Uiso 1 1 d . . . 
H6' H -0.422(5) 0.617(3) -0.103(3) 0.050(7) Uiso 1 1 d . . . 
H7 H -0.826(5) 0.620(3) -0.267(3) 0.051(7) Uiso 1 1 d . . . 
H8' H -0.554(5) 0.630(3) -0.478(3) 0.055(9) Uiso 1 1 d . . . 
H3' H -0.424(4) 1.032(2) -0.185(3) 0.038(6) Uiso 1 1 d . . . 
H6 H -0.290(5) 0.638(2) -0.220(3) 0.042(7) Uiso 1 1 d . . . 
H7' H -0.665(5) 0.494(3) -0.326(3) 0.045(7) Uiso 1 1 d . . . 
H8 H -0.835(6) 0.596(3) -0.510(3) 0.072(10) Uiso 1 1 d . . . 
H8" H -0.706(6) 0.753(4) -0.429(3) 0.077(10) Uiso 1 1 d . . . 
H2 H -0.082(4) 0.852(2) -0.124(2) 0.029(6) Uiso 1 1 d . . . 
  
  
_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 
O1 C1 1.413(2) . ? 
O1 C2 1.453(3) . ? 
F1 C4 1.330(3) . ? 
C1 C3 1.527(3) 2_575 ? 
C1 C5 1.536(3) . ? 
C1 C4 1.540(3) . ? 
O2 C2 1.387(3) . ? 
O2 C6 1.437(3) . ? 
F2 C4 1.327(2) . ? 
C2 C3 1.530(3) . ? 
F3 C4 1.324(3) . ? 
C3 C1 1.527(3) 2_575 ? 
F4 C5 1.333(3) . ? 
F5 C5 1.327(3) . ? 
C5 F6 1.338(3) . ? 
C6 C7 1.506(3) . ? 
C7 C8 1.510(4) . ? 
  
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 
C1 O1 C2 120.53(16) . . ? 
O1 C1 C3 116.09(17) . 2_575 ? 
O1 C1 C5 108.18(17) . . ? 
C3 C1 C5 108.44(18) 2_575 . ? 
O1 C1 C4 103.27(17) . . ? 
C3 C1 C4 111.06(19) 2_575 . ? 
C5 C1 C4 109.59(17) . . ? 
C2 O2 C6 116.08(17) . . ? 
O2 C2 O1 107.17(16) . . ? 
O2 C2 C3 105.92(17) . . ? 
O1 C2 C3 109.74(19) . . ? 
C1 C3 C2 116.69(19) 2_575 . ? 
F3 C4 F2 107.07(19) . . ? 
F3 C4 F1 106.52(19) . . ? 
F2 C4 F1 106.9(2) . . ? 
F3 C4 C1 113.1(2) . . ? 
F2 C4 C1 111.54(19) . . ? 
F1 C4 C1 111.28(17) . . ? 
F5 C5 F4 107.42(18) . . ? 
F5 C5 F6 106.2(2) . . ? 
F4 C5 F6 106.50(19) . . ? 
F5 C5 C1 113.4(2) . . ? 
F4 C5 C1 112.42(19) . . ? 
F6 C5 C1 110.52(18) . . ? 
O2 C6 C7 107.24(19) . . ? 
C6 C7 C8 112.9(2) . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C2 O1 C1 C3 32.9(3) . . . 2_575 ? 
C2 O1 C1 C5 -89.2(2) . . . . ? 
C2 O1 C1 C4 154.72(18) . . . . ? 
C6 O2 C2 O1 -78.4(2) . . . . ? 
C6 O2 C2 C3 164.5(2) . . . . ? 
C1 O1 C2 O2 143.75(18) . . . . ? 
C1 O1 C2 C3 -101.7(2) . . . . ? 
O2 C2 C3 C1 -135.6(2) . . . 2_575 ? 
O1 C2 C3 C1 109.0(2) . . . 2_575 ? 
O1 C1 C4 F3 56.3(2) . . . . ? 
C3 C1 C4 F3 -178.65(17) 2_575 . . . ? 
C5 C1 C4 F3 -58.9(2) . . . . ? 
O1 C1 C4 F2 177.04(17) . . . . ? 
C3 C1 C4 F2 -57.9(2) 2_575 . . . ? 
C5 C1 C4 F2 61.9(2) . . . . ? 
O1 C1 C4 F1 -63.6(2) . . . . ? 
C3 C1 C4 F1 61.5(2) 2_575 . . . ? 
C5 C1 C4 F1 -178.75(18) . . . . ? 
O1 C1 C5 F5 -53.5(2) . . . . ? 
C3 C1 C5 F5 179.79(19) 2_575 . . . ? 
C4 C1 C5 F5 58.4(2) . . . . ? 
O1 C1 C5 F4 -175.62(18) . . . . ? 
C3 C1 C5 F4 57.7(2) 2_575 . . . ? 
C4 C1 C5 F4 -63.7(2) . . . . ? 
O1 C1 C5 F6 65.5(2) . . . . ? 
C3 C1 C5 F6 -61.2(2) 2_575 . . . ? 
C4 C1 C5 F6 177.46(17) . . . . ? 
C2 O2 C6 C7 -161.5(2) . . . . ? 
O2 C6 C7 C8 60.7(3) . . . . ? 
  
_diffrn_measured_fraction_theta_max    0.986 
_diffrn_reflns_theta_full              28.02 
_diffrn_measured_fraction_theta_full   0.986 
_refine_diff_density_max    0.198 
_refine_diff_density_min   -0.301 
_refine_diff_density_rms    0.057 
#===END

data_07222
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C9 H12 F6 N0 O2'
_chemical_formula_weight          266.19
 
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'   0.0000   0.0000
 '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   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F'  'F'   0.0171   0.0103
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Tetragonal
_symmetry_space_group_name_H-M    P4(3)2(1)2
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 '-y+1/2, x+1/2, z+3/4'
 'y+1/2, -x+1/2, z+1/4'
 '-x+1/2, y+1/2, -z+3/4'
 'x+1/2, -y+1/2, -z+1/4'
 'y, x, -z'
 '-y, -x, -z+1/2'
 
_cell_length_a                    10.1499(12)
_cell_length_b                    10.1499(12)
_cell_length_c                    22.750(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2343.7(7)
_cell_formula_units_Z             8
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        ireg.block
_exptl_crystal_colour             colourless
_exptl_crystal_size_min           0.420
_exptl_crystal_size_mid           0.480
_exptl_crystal_size_max           0.480
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.509
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1088
_exptl_absorpt_coefficient_mu     0.166
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker P4'
_diffrn_measurement_method        'ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             28126
_diffrn_reflns_av_R_equivalents   0.0282
_diffrn_reflns_av_sigmaI/netI     0.0141
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -29
_diffrn_reflns_limit_l_max        30
_diffrn_reflns_theta_min          2.20
_diffrn_reflns_theta_max          28.29
_reflns_number_total              2920
_reflns_number_gt                 2662
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'Bruker XSCANS'
_computing_cell_refinement        'Bruker XSCANS'
_computing_data_reduction         'Bruker SHELXTL'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
 
_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)+(0.0326P)²+0.3048P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     riding
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.9(5)
_refine_ls_number_reflns          2920
_refine_ls_number_parameters      171
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0303
_refine_ls_R_factor_gt            0.0268
_refine_ls_wR_factor_ref          0.0686
_refine_ls_wR_factor_gt           0.0665
_refine_ls_goodness_of_fit_ref    1.057
_refine_ls_restrained_S_all       1.057
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
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
O1 O 0.35094(9) 0.99850(8) 0.25332(4) 0.0343(2) Uani 1 1 d . . .
F1 F 0.20745(9) 1.13294(9) 0.16794(4) 0.0531(2) Uani 1 1 d . . .
C1 C 0.41189(12) 1.06739(10) 0.20770(5) 0.0274(2) Uani 1 1 d . . .
O2 O 0.41670(9) 0.76758(7) 0.11298(3) 0.02879(18) Uani 1 1 d . . .
C2 C 0.43576(12) 0.97586(11) 0.15659(5) 0.0280(2) Uani 1 1 d . . .
H2 H 0.4718(13) 1.0107(14) 0.1222(6) 0.030(3) Uiso 1 1 d . . .
F2 F 0.37464(11) 1.25007(9) 0.14382(4) 0.0579(3) Uani 1 1 d . . .
F3 F 0.29205(10) 1.26386(8) 0.23099(4) 0.0502(2) Uani 1 1 d . . .
C3 C 0.40054(12) 0.85121(11) 0.15925(4) 0.0272(2) Uani 1 1 d . . .
H3 H 0.3615(14) 0.8151(14) 0.1946(6) 0.033(4) Uiso 1 1 d . . .
F4 F 0.53038(9) 1.20588(9) 0.27441(4) 0.0531(2) Uani 1 1 d . . .
C4 C 0.40800(11) 0.62444(10) 0.12603(5) 0.0256(2) Uani 1 1 d . . .
F5 F 0.61301(10) 1.18178(11) 0.18788(4) 0.0633(3) Uani 1 1 d . . .
C5 C 0.43264(15) 0.55974(12) 0.06706(5) 0.0388(3) Uani 1 1 d . . .
H5A H 0.5171 0.5866 0.0523 0.058 Uiso 1 1 calc R . .
H5B H 0.3652 0.5859 0.0399 0.058 Uiso 1 1 calc R . .
H5C H 0.4312 0.4657 0.0716 0.058 Uiso 1 1 calc R . .
F6 F 0.61912(9) 1.02290(10) 0.25002(5) 0.0618(3) Uani 1 1 d . . .
C6 C 0.51610(13) 0.58885(13) 0.16936(5) 0.0358(3) Uani 1 1 d . . .
H6A H 0.5024 0.6358 0.2055 0.054 Uiso 1 1 calc R . .
H6B H 0.6002 0.6125 0.1531 0.054 Uiso 1 1 calc R . .
H6C H 0.5140 0.4958 0.1768 0.054 Uiso 1 1 calc R . .
C7 C 0.27102(13) 0.59261(13) 0.14891(6) 0.0372(3) Uani 1 1 d . . .
H7A H 0.2600 0.6303 0.1873 0.056 Uiso 1 1 calc R . .
H7B H 0.2603 0.4988 0.1512 0.056 Uiso 1 1 calc R . .
H7C H 0.2062 0.6286 0.1227 0.056 Uiso 1 1 calc R . .
C9 C 0.32126(14) 1.18004(12) 0.18742(6) 0.0356(3) Uani 1 1 d . . .
C10 C 0.54494(14) 1.12109(14) 0.22981(6) 0.0398(3) Uani 1 1 d . . .
H1 H 0.3357(16) 1.0435(17) 0.2811(7) 0.050(5) Uiso 1 1 d . . .
 
 
_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
O1 C1 1.3959(13) . ?
F1 C9 1.3265(16) . ?
C1 C2 1.5079(15) . ?
C1 C9 1.5383(17) . ?
C1 C10 1.5407(18) . ?
O2 C3 1.3621(13) . ?
O2 C4 1.4855(12) . ?
C2 C3 1.3161(16) . ?
F2 C9 1.3352(15) . ?
F3 C9 1.3395(14) . ?
F4 C10 1.3388(15) . ?
C4 C5 1.5145(15) . ?
C4 C6 1.5185(16) . ?
C4 C7 1.5193(17) . ?
F5 C10 1.3292(16) . ?
F6 C10 1.3310(18) . ?
 
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
O1 C1 C2 109.63(9) . . ?
O1 C1 C9 109.29(10) . . ?
C2 C1 C9 108.83(10) . . ?
O1 C1 C10 108.84(10) . . ?
C2 C1 C10 109.20(10) . . ?
C9 C1 C10 111.04(10) . . ?
C3 O2 C4 116.61(8) . . ?
C3 C2 C1 120.88(10) . . ?
C2 C3 O2 122.06(10) . . ?
O2 C4 C5 103.72(8) . . ?
O2 C4 C6 108.63(9) . . ?
C5 C4 C6 110.64(10) . . ?
O2 C4 C7 109.32(9) . . ?
C5 C4 C7 111.25(10) . . ?
C6 C4 C7 112.85(10) . . ?
F1 C9 F2 107.28(11) . . ?
F1 C9 F3 106.46(11) . . ?
F2 C9 F3 107.55(10) . . ?
F1 C9 C1 110.67(10) . . ?
F2 C9 C1 112.08(11) . . ?
F3 C9 C1 112.49(10) . . ?
F5 C10 F6 107.51(12) . . ?
F5 C10 F4 107.66(11) . . ?
F6 C10 F4 106.38(11) . . ?
F5 C10 C1 112.66(11) . . ?
F6 C10 C1 110.10(11) . . ?
F4 C10 C1 112.22(10) . . ?
 
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
O1 C1 C2 C3 -0.04(16) . . . . ?
C9 C1 C2 C3 -119.52(12) . . . . ?
C10 C1 C2 C3 119.12(13) . . . . ?
C1 C2 C3 O2 177.62(11) . . . . ?
C4 O2 C3 C2 163.83(11) . . . . ?
C3 O2 C4 C5 -178.83(10) . . . . ?
C3 O2 C4 C6 -61.10(12) . . . . ?
C3 O2 C4 C7 62.43(12) . . . . ?
O1 C1 C9 F1 -60.51(13) . . . . ?
C2 C1 C9 F1 59.18(13) . . . . ?
C10 C1 C9 F1 179.40(10) . . . . ?
O1 C1 C9 F2 179.78(10) . . . . ?
C2 C1 C9 F2 -60.54(13) . . . . ?
C10 C1 C9 F2 59.69(13) . . . . ?
O1 C1 C9 F3 58.44(13) . . . . ?
C2 C1 C9 F3 178.13(10) . . . . ?
C10 C1 C9 F3 -61.65(13) . . . . ?
O1 C1 C10 F5 176.37(10) . . . . ?
C2 C1 C10 F5 56.73(14) . . . . ?
C9 C1 C10 F5 -63.28(14) . . . . ?
O1 C1 C10 F6 56.37(12) . . . . ?
C2 C1 C10 F6 -63.28(13) . . . . ?
C9 C1 C10 F6 176.71(10) . . . . ?
O1 C1 C10 F4 -61.91(14) . . . . ?
C2 C1 C10 F4 178.44(10) . . . . ?
C9 C1 C10 F4 58.43(14) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              28.29
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.172
_refine_diff_density_min   -0.157
_refine_diff_density_rms    0.032
#===END

data_07077
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C10 H6 F12 O S2'
_chemical_formula_weight          434.27
 
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'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F'  'F'   0.0171   0.0103
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    Ccca
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y+1/2, z'
 'x, -y+1/2, -z+1/2'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, -y+1, z'
 'x+1/2, -y+1, -z+1/2'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, y-1/2, -z'
 '-x, y-1/2, z-1/2'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, y, -z'
 '-x+1/2, y, z-1/2'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    21.271(6)
_cell_length_b                    25.685(7)
_cell_length_c                    10.563(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      5771(3)
_cell_formula_units_Z             16
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        ireg.block
_exptl_crystal_colour             colourless
_exptl_crystal_size_min           0.480
_exptl_crystal_size_mid           0.500
_exptl_crystal_size_max           0.500
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.999
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              3424
_exptl_absorpt_coefficient_mu     0.508
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker P4'
_diffrn_measurement_method        'ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             32649
_diffrn_reflns_av_R_equivalents   0.0349
_diffrn_reflns_av_sigmaI/netI     0.0181
_diffrn_reflns_limit_h_min        -25
_diffrn_reflns_limit_h_max        28
_diffrn_reflns_limit_k_min        -34
_diffrn_reflns_limit_k_max        34
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          1.91
_diffrn_reflns_theta_max          28.31
_reflns_number_total              3592
_reflns_number_gt                 3020
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'Bruker XSCANS'
_computing_cell_refinement        'Bruker XSCANS'
_computing_data_reduction         'Bruker SHELXTL'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
 
_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)+(0.0350P)²+6.7987P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     riding
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3592
_refine_ls_number_parameters      250
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0402
_refine_ls_R_factor_gt            0.0308
_refine_ls_wR_factor_ref          0.0825
_refine_ls_wR_factor_gt           0.0745
_refine_ls_goodness_of_fit_ref    1.044
_refine_ls_restrained_S_all       1.044
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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
S1 S 0.21132(2) 0.078508(19) 0.27081(5) 0.04047(12) Uani 1 1 d . . .
S2 S 0.062314(18) 0.195155(14) 0.13788(3) 0.02594(10) Uani 1 1 d . . .
F1 F 0.10031(7) 0.00665(4) 0.22684(13) 0.0624(4) Uani 1 1 d . . .
F2 F 0.15402(7) -0.01518(5) 0.38989(15) 0.0643(4) Uani 1 1 d . . .
F3 F 0.05914(6) 0.01217(5) 0.41037(15) 0.0638(4) Uani 1 1 d . . .
F4 F 0.19079(6) 0.05952(5) 0.55063(12) 0.0572(3) Uani 1 1 d . . .
F5 F 0.09558(6) 0.08563(6) 0.56378(10) 0.0557(3) Uani 1 1 d . . .
F6 F 0.16832(7) 0.13858(5) 0.50713(11) 0.0541(3) Uani 1 1 d . . .
F7 F 0.03983(6) 0.10507(5) -0.04191(12) 0.0547(3) Uani 1 1 d . . .
F8 F 0.02617(7) 0.18010(6) -0.12614(13) 0.0687(4) Uani 1 1 d . . .
F9 F 0.10154(8) 0.13062(7) -0.18955(12) 0.0766(5) Uani 1 1 d . . .
F10 F 0.18747(6) 0.23817(5) 0.04223(12) 0.0532(3) Uani 1 1 d . . .
F11 F 0.11220(7) 0.25415(5) -0.08646(13) 0.0594(3) Uani 1 1 d . . .
F12 F 0.18665(7) 0.20225(5) -0.14088(12) 0.0642(4) Uani 1 1 d . . .
O1 O 0.16917(5) 0.17579(4) 0.25840(11) 0.0298(2) Uani 1 1 d . . .
C1 C 0.13635(7) 0.07553(6) 0.35589(15) 0.0282(3) Uani 1 1 d . . .
C2 C 0.08512(7) 0.11107(6) 0.29903(14) 0.0241(3) Uani 1 1 d . . .
C3 C 0.10440(7) 0.16801(6) 0.27470(14) 0.0242(3) Uani 1 1 d . . .
C4 C 0.11376(8) 0.17036(6) 0.01197(14) 0.0284(3) Uani 1 1 d . . .
C5 C 0.15967(8) 0.12727(7) 0.05646(16) 0.0314(3) Uani 1 1 d . . .
C6 C 0.19658(8) 0.13830(7) 0.17916(16) 0.0324(3) Uani 1 1 d . . .
C7 C 0.11229(10) 0.01916(7) 0.34643(19) 0.0423(4) Uani 1 1 d . . .
C8 C 0.14779(9) 0.08964(8) 0.49583(17) 0.0388(4) Uani 1 1 d . . .
C9 C 0.07004(10) 0.14650(8) -0.08817(18) 0.0459(5) Uani 1 1 d . . .
C10 C 0.15039(10) 0.21686(7) -0.04405(18) 0.0422(4) Uani 1 1 d . . .
H3 H 0.0926(8) 0.1893(7) 0.3434(17) 0.022(4) Uiso 1 1 d . . .
H2' H 0.0718(9) 0.0949(7) 0.2240(18) 0.028(5) Uiso 1 1 d . . .
H6 H 0.2382(10) 0.1521(7) 0.1589(19) 0.039(5) Uiso 1 1 d . . .
H2 H 0.0505(9) 0.1105(7) 0.3550(18) 0.029(5) Uiso 1 1 d . . .
H5' H 0.1352(9) 0.0950(8) 0.0622(19) 0.038(5) Uiso 1 1 d . . .
H5 H 0.1887(10) 0.1221(8) -0.009(2) 0.044(6) Uiso 1 1 d . . .
 
 
_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
S1 C1 1.8321(17) . ?
S1 C6 1.8422(18) . ?
S2 C4 1.8363(16) . ?
S2 C3 1.8374(15) . ?
F1 C7 1.328(2) . ?
F2 C7 1.333(2) . ?
F3 C7 1.329(2) . ?
F4 C8 1.330(2) . ?
F5 C8 1.326(2) . ?
F6 C8 1.336(2) . ?
F7 C9 1.336(3) . ?
F8 C9 1.333(2) . ?
F9 C9 1.327(2) . ?
F10 C10 1.324(2) . ?
F11 C10 1.333(2) . ?
F12 C10 1.335(2) . ?
O1 C3 1.4028(18) . ?
O1 C6 1.403(2) . ?
C1 C7 1.539(2) . ?
C1 C8 1.541(2) . ?
C1 C2 1.543(2) . ?
C2 C3 1.541(2) . ?
C4 C9 1.536(2) . ?
C4 C10 1.544(2) . ?
C4 C5 1.549(2) . ?
C5 C6 1.542(2) . ?
 
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
C1 S1 C6 98.31(7) . . ?
C4 S2 C3 98.50(7) . . ?
C3 O1 C6 112.57(12) . . ?
C7 C1 C8 109.63(14) . . ?
C7 C1 C2 107.24(14) . . ?
C8 C1 C2 110.23(13) . . ?
C7 C1 S1 107.27(12) . . ?
C8 C1 S1 108.86(12) . . ?
C2 C1 S1 113.52(11) . . ?
C3 C2 C1 116.01(13) . . ?
O1 C3 C2 114.65(12) . . ?
O1 C3 S2 109.14(10) . . ?
C2 C3 S2 111.21(10) . . ?
C9 C4 C10 110.50(15) . . ?
C9 C4 C5 107.79(14) . . ?
C10 C4 C5 110.54(14) . . ?
C9 C4 S2 106.04(12) . . ?
C10 C4 S2 108.07(11) . . ?
C5 C4 S2 113.81(11) . . ?
C6 C5 C4 116.42(13) . . ?
O1 C6 C5 114.58(13) . . ?
O1 C6 S1 109.23(11) . . ?
C5 C6 S1 112.05(12) . . ?
F1 C7 F3 106.69(18) . . ?
F1 C7 F2 107.16(16) . . ?
F3 C7 F2 107.58(16) . . ?
F1 C7 C1 110.69(15) . . ?
F3 C7 C1 112.15(15) . . ?
F2 C7 C1 112.27(17) . . ?
F5 C8 F4 107.16(15) . . ?
F5 C8 F6 107.36(16) . . ?
F4 C8 F6 106.48(15) . . ?
F5 C8 C1 111.62(15) . . ?
F4 C8 C1 112.90(16) . . ?
F6 C8 C1 111.00(14) . . ?
F9 C9 F8 108.04(17) . . ?
F9 C9 F7 107.04(17) . . ?
F8 C9 F7 106.80(18) . . ?
F9 C9 C4 111.88(17) . . ?
F8 C9 C4 111.88(16) . . ?
F7 C9 C4 110.93(15) . . ?
F10 C10 F11 107.29(16) . . ?
F10 C10 F12 107.42(17) . . ?
F11 C10 F12 107.25(15) . . ?
F10 C10 C4 110.90(14) . . ?
F11 C10 C4 112.15(16) . . ?
F12 C10 C4 111.59(15) . . ?
 
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 S1 C1 C7 133.53(12) . . . . ?
C6 S1 C1 C8 -107.92(12) . . . . ?
C6 S1 C1 C2 15.25(13) . . . . ?
C7 C1 C2 C3 -168.44(14) . . . . ?
C8 C1 C2 C3 72.26(17) . . . . ?
S1 C1 C2 C3 -50.15(16) . . . . ?
C6 O1 C3 C2 44.21(17) . . . . ?
C6 O1 C3 S2 -81.28(13) . . . . ?
C1 C2 C3 O1 24.30(18) . . . . ?
C1 C2 C3 S2 148.71(11) . . . . ?
C4 S2 C3 O1 43.89(11) . . . . ?
C4 S2 C3 C2 -83.57(11) . . . . ?
C3 S2 C4 C9 132.68(12) . . . . ?
C3 S2 C4 C10 -108.82(12) . . . . ?
C3 S2 C4 C5 14.37(13) . . . . ?
C9 C4 C5 C6 -165.27(15) . . . . ?
C10 C4 C5 C6 73.87(18) . . . . ?
S2 C4 C5 C6 -47.96(18) . . . . ?
C3 O1 C6 C5 46.05(18) . . . . ?
C3 O1 C6 S1 -80.59(13) . . . . ?
C4 C5 C6 O1 21.7(2) . . . . ?
C4 C5 C6 S1 146.89(12) . . . . ?
C1 S1 C6 O1 43.88(12) . . . . ?
C1 S1 C6 C5 -84.20(12) . . . . ?
C8 C1 C7 F1 178.14(15) . . . . ?
C2 C1 C7 F1 58.47(19) . . . . ?
S1 C1 C7 F1 -63.81(17) . . . . ?
C8 C1 C7 F3 59.1(2) . . . . ?
C2 C1 C7 F3 -60.56(19) . . . . ?
S1 C1 C7 F3 177.16(13) . . . . ?
C8 C1 C7 F2 -62.2(2) . . . . ?
C2 C1 C7 F2 178.17(15) . . . . ?
S1 C1 C7 F2 55.89(18) . . . . ?
C7 C1 C8 F5 -59.82(19) . . . . ?
C2 C1 C8 F5 58.01(19) . . . . ?
S1 C1 C8 F5 -176.87(13) . . . . ?
C7 C1 C8 F4 61.0(2) . . . . ?
C2 C1 C8 F4 178.80(14) . . . . ?
S1 C1 C8 F4 -56.08(18) . . . . ?
C7 C1 C8 F6 -179.56(15) . . . . ?
C2 C1 C8 F6 -61.73(19) . . . . ?
S1 C1 C8 F6 63.39(16) . . . . ?
C10 C4 C9 F9 58.3(2) . . . . ?
C5 C4 C9 F9 -62.6(2) . . . . ?
S2 C4 C9 F9 175.18(15) . . . . ?
C10 C4 C9 F8 -63.1(2) . . . . ?
C5 C4 C9 F8 176.02(16) . . . . ?
S2 C4 C9 F8 53.79(19) . . . . ?
C10 C4 C9 F7 177.76(15) . . . . ?
C5 C4 C9 F7 56.87(19) . . . . ?
S2 C4 C9 F7 -65.36(17) . . . . ?
C9 C4 C10 F10 179.02(15) . . . . ?
C5 C4 C10 F10 -61.74(18) . . . . ?
S2 C4 C10 F10 63.41(17) . . . . ?
C9 C4 C10 F11 59.1(2) . . . . ?
C5 C4 C10 F11 178.33(14) . . . . ?
S2 C4 C10 F11 -56.52(18) . . . . ?
C9 C4 C10 F12 -61.3(2) . . . . ?
C5 C4 C10 F12 58.0(2) . . . . ?
S2 C4 C10 F12 -176.87(14) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              28.31
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.428
_refine_diff_density_min   -0.309
_refine_diff_density_rms    0.050
#===END
