data_2e _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H5 Br F6 O3 S' _chemical_formula_weight 399.11 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' 'S' 'S' 0.1246 0.1234 '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' _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 7.8097(5) _cell_length_b 8.4203(5) _cell_length_c 10.7272(6) _cell_angle_alpha 98.112(4) _cell_angle_beta 95.627(4) _cell_angle_gamma 98.351(4) _cell_volume 685.88(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3423 _cell_measurement_theta_min 2.476 _cell_measurement_theta_max 26.683 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.933 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 3.224 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.4447 _exptl_absorpt_correction_T_max 0.4447 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7205 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2413 _reflns_number_gt 1928 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.057(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2413 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1340 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _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 Br1 Br 0.31584(5) 0.26427(6) 0.10055(4) 0.0808(3) Uani 1 1 d . . . S1 S 0.18679(13) 0.33379(10) -0.36234(8) 0.0602(3) Uani 1 1 d . . . O1 O 0.1198(3) 0.1456(3) -0.3675(2) 0.0532(6) Uani 1 1 d . . . F2 F 0.4627(3) 0.0364(3) -0.3546(3) 0.0866(7) Uani 1 1 d . . . C6 C 0.0851(5) 0.2521(4) 0.0195(3) 0.0520(8) Uani 1 1 d . . . F3 F 0.2465(3) -0.1229(3) -0.4536(3) 0.0970(9) Uani 1 1 d . . . C1 C 0.0390(4) 0.1627(4) -0.1011(3) 0.0493(7) Uani 1 1 d . . . O3 O 0.0415(5) 0.4134(4) -0.3618(3) 0.0901(10) Uani 1 1 d . . . C5 C -0.0277(5) 0.3364(4) 0.0817(3) 0.0601(9) Uani 1 1 d . . . H5A H 0.0070 0.3945 0.1628 0.072 Uiso 1 1 calc R . . C9 C 0.3117(5) -0.0485(4) -0.3395(4) 0.0610(9) Uani 1 1 d . . . F5 F 0.1182(4) 0.2561(4) -0.6061(2) 0.1002(9) Uani 1 1 d . . . C2 C -0.1291(5) 0.1637(4) -0.1582(4) 0.0623(9) Uani 1 1 d . . . H2A H -0.1650 0.1057 -0.2392 0.075 Uiso 1 1 calc R . . C8 C 0.1934(4) 0.0566(4) -0.2805(3) 0.0501(7) Uani 1 1 d . . . C7 C 0.1581(4) 0.0669(4) -0.1631(3) 0.0527(8) Uani 1 1 d . . . H7A H 0.2161 0.0054 -0.1126 0.063 Uiso 1 1 calc R . . C10 C 0.2511(5) 0.3265(5) -0.5235(4) 0.0674(10) Uani 1 1 d . . . O2 O 0.3356(4) 0.3847(3) -0.2733(3) 0.0900(10) Uani 1 1 d . . . F1 F 0.3464(5) -0.1587(4) -0.2694(3) 0.1148(12) Uani 1 1 d . . . C4 C -0.1916(5) 0.3337(4) 0.0229(4) 0.0629(10) Uani 1 1 d . . . H4A H -0.2688 0.3900 0.0647 0.075 Uiso 1 1 calc R . . F6 F 0.3812(5) 0.2480(4) -0.5341(3) 0.1118(11) Uani 1 1 d . . . C3 C -0.2440(5) 0.2490(5) -0.0970(4) 0.0680(10) Uani 1 1 d . . . H3B H -0.3553 0.2489 -0.1368 0.082 Uiso 1 1 calc R . . F4 F 0.2967(4) 0.4739(3) -0.5441(3) 0.0987(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0712(4) 0.1173(4) 0.0517(3) 0.0050(2) -0.0020(2) 0.0221(3) S1 0.0753(7) 0.0600(5) 0.0459(5) -0.0031(4) 0.0051(4) 0.0254(4) O1 0.0552(13) 0.0647(13) 0.0390(12) 0.0000(9) 0.0025(10) 0.0177(10) F2 0.0623(15) 0.1062(17) 0.0922(18) -0.0054(14) 0.0253(13) 0.0265(13) C6 0.061(2) 0.0580(17) 0.0395(17) 0.0094(14) 0.0131(14) 0.0120(15) F3 0.0857(18) 0.1133(18) 0.0806(18) -0.0414(14) 0.0051(14) 0.0371(14) C1 0.0540(19) 0.0565(16) 0.0395(17) 0.0068(13) 0.0127(14) 0.0117(13) O3 0.118(3) 0.097(2) 0.075(2) 0.0157(16) 0.0319(18) 0.0685(19) C5 0.074(3) 0.0617(18) 0.0452(19) 0.0017(15) 0.0246(17) 0.0072(16) C9 0.061(2) 0.072(2) 0.054(2) 0.0025(17) 0.0117(17) 0.0253(17) F5 0.110(2) 0.131(2) 0.0494(14) 0.0063(14) 0.0090(13) -0.0051(17) C2 0.056(2) 0.071(2) 0.057(2) -0.0051(17) 0.0110(17) 0.0121(17) C8 0.0481(18) 0.0600(17) 0.0427(18) 0.0011(13) 0.0045(14) 0.0175(14) C7 0.054(2) 0.0587(17) 0.0478(19) 0.0062(14) 0.0107(15) 0.0177(14) C10 0.066(2) 0.075(2) 0.067(3) 0.0132(19) 0.020(2) 0.0198(19) O2 0.107(2) 0.0732(16) 0.074(2) -0.0070(14) -0.0275(17) 0.0048(15) F1 0.151(3) 0.123(2) 0.113(2) 0.0524(19) 0.065(2) 0.097(2) C4 0.065(2) 0.0609(19) 0.069(3) 0.0092(17) 0.032(2) 0.0157(17) F6 0.118(2) 0.133(2) 0.119(2) 0.0458(19) 0.066(2) 0.073(2) C3 0.049(2) 0.078(2) 0.077(3) 0.003(2) 0.0150(17) 0.0141(16) F4 0.101(2) 0.0931(17) 0.113(2) 0.0431(16) 0.0269(16) 0.0181(14) _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 C6 1.905(4) . ? S1 O3 1.399(3) . ? S1 O2 1.403(3) . ? S1 O1 1.587(2) . ? S1 C10 1.842(4) . ? O1 C8 1.407(4) . ? F2 C9 1.324(4) . ? C6 C5 1.374(5) . ? C6 C1 1.387(5) . ? F3 C9 1.312(4) . ? C1 C2 1.395(5) . ? C1 C7 1.466(5) . ? C5 C4 1.366(6) . ? C9 F1 1.315(5) . ? C9 C8 1.494(5) . ? F5 C10 1.306(5) . ? C2 C3 1.386(5) . ? C8 C7 1.308(5) . ? C10 F6 1.295(5) . ? C10 F4 1.296(5) . ? C4 C3 1.372(6) . ? 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 O3 S1 O2 122.4(2) . . ? O3 S1 O1 107.83(18) . . ? O2 S1 O1 110.16(16) . . ? O3 S1 C10 105.95(19) . . ? O2 S1 C10 109.2(2) . . ? O1 S1 C10 98.49(15) . . ? C8 O1 S1 121.4(2) . . ? C5 C6 C1 122.6(4) . . ? C5 C6 Br1 118.5(3) . . ? C1 C6 Br1 118.9(3) . . ? C6 C1 C2 116.6(3) . . ? C6 C1 C7 121.7(3) . . ? C2 C1 C7 121.7(3) . . ? C4 C5 C6 119.2(3) . . ? F3 C9 F1 108.4(3) . . ? F3 C9 F2 104.9(3) . . ? F1 C9 F2 107.2(3) . . ? F3 C9 C8 112.4(3) . . ? F1 C9 C8 111.4(3) . . ? F2 C9 C8 112.1(3) . . ? C3 C2 C1 121.5(4) . . ? C7 C8 O1 122.6(3) . . ? C7 C8 C9 125.7(3) . . ? O1 C8 C9 111.7(3) . . ? C8 C7 C1 128.3(3) . . ? F6 C10 F4 109.4(3) . . ? F6 C10 F5 110.4(4) . . ? F4 C10 F5 108.8(4) . . ? F6 C10 S1 110.1(3) . . ? F4 C10 S1 108.8(3) . . ? F5 C10 S1 109.3(3) . . ? C5 C4 C3 120.9(3) . . ? C4 C3 C2 119.3(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.609 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.077 #===END data_3q _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 Cl F3' _chemical_formula_weight 296.71 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.892(5) _cell_length_b 11.809(10) _cell_length_c 20.667(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1438(2) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 3807 _cell_measurement_theta_min 2.6095 _cell_measurement_theta_max 25.6025 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.285 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.9194 _exptl_absorpt_correction_T_max 0.9194 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12129 _diffrn_reflns_av_R_equivalents 0.1061 _diffrn_reflns_av_sigmaI/netI 0.0840 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2469 _reflns_number_gt 1715 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0932P)^2^+0.0614P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.132(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.27(14) _refine_ls_number_reflns 2469 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0950 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1527 _refine_ls_wR_factor_gt 0.1386 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 Cl1 Cl 1.2607(2) 0.35671(10) 1.09394(7) 0.0970(5) Uani 1 1 d . . . C16 C 0.3440(6) -0.1512(4) 1.20007(19) 0.0627(10) Uani 1 1 d . . . F3 F 0.3637(5) -0.1395(3) 1.26358(11) 0.1078(11) Uani 1 1 d . . . C10 C 0.2476(7) -0.0356(3) 1.06030(16) 0.0575(9) Uani 1 1 d . . . H10A H 0.1328 -0.0046 1.0856 0.069 Uiso 1 1 calc R . . C2 C 0.7330(6) 0.1467(3) 1.10667(17) 0.0564(9) Uani 1 1 d . . . H2A H 0.6077 0.1283 1.0814 0.068 Uiso 1 1 calc R . . C11 C 0.2221(7) -0.0409(4) 0.99354(18) 0.0649(10) Uani 1 1 d . . . H11A H 0.0916 -0.0113 0.9747 0.078 Uiso 1 1 calc R . . C1 C 0.7687(5) 0.0900(3) 1.16506(15) 0.0492(8) Uani 1 1 d . . . C3 C 0.8812(7) 0.2294(3) 1.08598(19) 0.0624(10) Uani 1 1 d . . . H3A H 0.8530 0.2677 1.0475 0.075 Uiso 1 1 calc R . . C7 C 0.6188(6) 0.0014(3) 1.19146(16) 0.0533(9) Uani 1 1 d . . . H7A H 0.6239 -0.0071 1.2362 0.064 Uiso 1 1 calc R . . F2 F 0.1216(4) -0.1487(2) 1.18744(12) 0.0902(8) Uani 1 1 d . . . C9 C 0.4438(5) -0.0762(3) 1.08940(15) 0.0454(8) Uani 1 1 d . . . C14 C 0.6066(6) -0.1259(3) 1.05013(17) 0.0565(9) Uani 1 1 d . . . H14A H 0.7372 -0.1559 1.0687 0.068 Uiso 1 1 calc R . . C5 C 1.1118(7) 0.2016(3) 1.17953(19) 0.0632(10) Uani 1 1 d . . . H5A H 1.2405 0.2192 1.2036 0.076 Uiso 1 1 calc R . . C8 C 0.4773(5) -0.0682(3) 1.16094(15) 0.0473(9) Uani 1 1 d . . . C13 C 0.5779(7) -0.1318(3) 0.98359(18) 0.0644(10) Uani 1 1 d . . . H13A H 0.6904 -0.1650 0.9584 0.077 Uiso 1 1 calc R . . C12 C 0.3870(7) -0.0896(3) 0.95420(17) 0.0612(10) Uani 1 1 d . . . F1 F 0.4041(5) -0.2586(2) 1.18747(15) 0.1032(10) Uani 1 1 d . . . C4 C 1.0696(6) 0.2556(3) 1.1217(2) 0.0596(10) Uani 1 1 d . . . C15 C 0.3546(9) -0.0926(5) 0.88129(19) 0.0962(16) Uani 1 1 d . . . H15A H 0.2111 -0.0591 0.8704 0.144 Uiso 1 1 calc R . . H15B H 0.3578 -0.1697 0.8666 0.144 Uiso 1 1 calc R . . H15C H 0.4745 -0.0508 0.8608 0.144 Uiso 1 1 calc R . . C6 C 0.9602(6) 0.1209(4) 1.20125(16) 0.0579(10) Uani 1 1 d . . . H6A H 0.9859 0.0860 1.2409 0.070 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0737(8) 0.0703(8) 0.1470(12) 0.0208(7) 0.0109(7) -0.0111(7) C16 0.062(2) 0.059(3) 0.067(3) 0.010(2) 0.0071(18) 0.000(2) F3 0.135(3) 0.127(2) 0.0620(15) 0.0209(15) 0.0151(14) -0.044(2) C10 0.051(2) 0.061(2) 0.061(2) -0.0037(18) -0.0033(17) 0.010(2) C2 0.0520(19) 0.053(2) 0.064(2) 0.0081(17) -0.0094(17) 0.003(2) C11 0.059(2) 0.068(2) 0.068(2) 0.005(2) -0.0208(19) -0.001(2) C1 0.0497(18) 0.0501(19) 0.0477(19) -0.0058(15) 0.0026(15) 0.0085(19) C3 0.068(2) 0.052(2) 0.068(2) 0.0099(19) -0.003(2) 0.010(2) C7 0.054(2) 0.058(2) 0.0480(19) 0.0049(17) 0.0037(17) 0.0029(19) F2 0.0609(14) 0.094(2) 0.1157(19) 0.0307(17) 0.0125(13) -0.0109(15) C9 0.0428(16) 0.0424(19) 0.0509(18) 0.0021(16) 0.0021(15) -0.0007(15) C14 0.0525(19) 0.057(2) 0.060(2) 0.0054(18) 0.0024(17) 0.008(2) C5 0.054(2) 0.059(2) 0.076(3) -0.017(2) -0.004(2) 0.001(2) C8 0.0436(18) 0.046(2) 0.0518(19) 0.0076(16) 0.0051(15) 0.0046(16) C13 0.070(2) 0.061(3) 0.063(2) -0.008(2) 0.018(2) 0.008(2) C12 0.078(3) 0.055(2) 0.050(2) -0.0002(18) 0.002(2) -0.017(2) F1 0.118(2) 0.0562(16) 0.135(2) 0.0273(15) 0.0431(19) 0.0123(16) C4 0.052(2) 0.050(2) 0.077(3) -0.003(2) 0.0052(19) 0.0076(19) C15 0.128(4) 0.105(4) 0.056(2) 0.006(2) -0.007(3) -0.028(3) C6 0.060(2) 0.064(2) 0.0498(18) -0.0052(18) -0.0021(17) 0.002(2) _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 Cl1 C4 1.739(4) . ? C16 F3 1.325(4) . ? C16 F2 1.336(4) . ? C16 F1 1.342(5) . ? C16 C8 1.494(5) . ? C10 C11 1.389(5) . ? C10 C9 1.388(5) . ? C2 C3 1.379(5) . ? C2 C1 1.396(5) . ? C11 C12 1.391(6) . ? C1 C6 1.402(5) . ? C1 C7 1.474(5) . ? C3 C4 1.369(6) . ? C7 C8 1.330(5) . ? C9 C14 1.387(5) . ? C9 C8 1.495(5) . ? C14 C13 1.387(5) . ? C5 C4 1.377(5) . ? C5 C6 1.381(5) . ? C13 C12 1.372(6) . ? C12 C15 1.519(5) . ? 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 F3 C16 F2 106.1(3) . . ? F3 C16 F1 105.5(4) . . ? F2 C16 F1 104.0(4) . . ? F3 C16 C8 115.0(4) . . ? F2 C16 C8 113.3(4) . . ? F1 C16 C8 112.1(3) . . ? C11 C10 C9 120.3(4) . . ? C3 C2 C1 120.8(3) . . ? C10 C11 C12 121.6(4) . . ? C2 C1 C6 117.3(3) . . ? C2 C1 C7 124.7(3) . . ? C6 C1 C7 118.0(3) . . ? C4 C3 C2 120.4(4) . . ? C8 C7 C1 129.7(3) . . ? C14 C9 C10 117.9(3) . . ? C14 C9 C8 121.0(3) . . ? C10 C9 C8 121.1(3) . . ? C13 C14 C9 121.1(3) . . ? C4 C5 C6 119.0(3) . . ? C7 C8 C9 126.3(3) . . ? C7 C8 C16 118.6(3) . . ? C9 C8 C16 115.1(3) . . ? C12 C13 C14 121.4(3) . . ? C13 C12 C11 117.6(3) . . ? C13 C12 C15 122.2(4) . . ? C11 C12 C15 120.1(4) . . ? C5 C4 C3 120.7(4) . . ? C5 C4 Cl1 119.2(3) . . ? C3 C4 Cl1 120.1(3) . . ? C5 C6 C1 121.8(3) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.166 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.042