#------------------------------------------------------------------------------ #$Date: 2023-11-24 02:38:02 +0200 (Fri, 24 Nov 2023) $ #$Revision: 287767 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247785.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7247785 loop_ _publ_author_name 'Lamba, Manisha' 'Singh, Prasoon Raj' 'Bhatt, Shubham' 'Goswami, Avijit' _publ_section_title ; Metal- and Additive-Free TfOH Catalyzed Chemoselective O- and S-Trifluoroethylation of Oxindoles, Isoindolines and Thioxindoles ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D3GC03702A _journal_year 2023 _chemical_formula_moiety 'C22 H15 F4 N S' _chemical_formula_sum 'C22 H15 F4 N S' _chemical_formula_weight 401.41 _space_group_crystal_system orthorhombic _space_group_IT_number 29 _space_group_name_Hall 'P 2c -2ac' _space_group_name_H-M_alt 'P c a 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2023-04-19 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _audit_update_record ; 2023-04-19 deposited with the CCDC. 2023-11-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.8631(3) _cell_length_b 16.0474(5) _cell_length_c 16.9025(6) _cell_measurement_reflns_used 5820 _cell_measurement_temperature 298 _cell_measurement_theta_max 26.36 _cell_measurement_theta_min 2.72 _cell_volume 1861.56(12) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 298 _diffrn_detector 'Bruker APEX2 area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART APEX2 area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_unetI/netI 0.0601 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 9025 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.417 _diffrn_reflns_theta_min 2.724 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_type 'Incoatec I\ms' _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.4960 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1546 before and 0.0711 after correction. The Ratio of minimum to maximum transmission is 0.6654. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.432 _exptl_crystal_description block _exptl_crystal_F_000 824 _exptl_crystal_size_max 0.235 _exptl_crystal_size_mid 0.123 _exptl_crystal_size_min 0.098 _refine_diff_density_max 0.213 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.044 _refine_ls_abs_structure_details ; Flack x determined using 1428 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.03(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 257 _refine_ls_number_reflns 3786 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.045 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0441 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.2850P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1068 _refine_ls_wR_factor_ref 0.1112 _reflns_Friedel_coverage 0.912 _reflns_Friedel_fraction_full 0.983 _reflns_Friedel_fraction_max 0.979 _reflns_number_gt 3446 _reflns_number_total 3786 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03702a2.cif _cod_data_source_block agml_868_0ma_a _cod_database_code 7247785 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.979 _shelx_estimated_absorpt_t_min 0.950 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B) 2.b Aromatic/amide H refined with riding coordinates: C14(H14), C13(H13), C12(H12), C21(H21), C20(H20), C18(H18), C15(H15), C10(H10), C9(H9), C8(H8), C7(H7), C6(H6) ; _shelx_res_file ; TITL agml_368_0ma_a.res in Pca2(1) agml_368_0ma_a.res created by SHELXL-2018/3 at 11:34:30 on 19-Apr-2023 CELL 0.71073 6.8631 16.0474 16.9025 90 90 90 ZERR 4 0.0003 0.0005 0.0006 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5-X,+Y,0.5+Z SYMM 0.5+X,-Y,+Z SFAC C H F N S UNIT 88 60 16 4 4 L.S. 4 PLAN 1 0 0 SIZE 0.235 0.123 0.098 TEMP 24.85 CONF HTAB BOND $H MORE -1 fmap 2 acta REM REM REM WGHT 0.050900 0.285000 FVAR 0.99385 S1 5 0.788920 0.686100 0.504281 11.00000 0.03716 0.05422 = 0.03808 -0.00308 0.00143 0.00961 F2 3 0.667490 0.599862 0.662071 11.00000 0.10223 0.08851 = 0.10168 0.02257 0.04277 -0.00503 F3 3 0.902914 0.535712 0.608856 11.00000 0.15477 0.05363 = 0.08540 -0.00229 0.00061 0.03410 F1 3 0.948318 0.604966 0.714319 11.00000 0.19368 0.10131 = 0.06488 0.01706 -0.05569 0.00477 F4 3 -0.138240 0.941701 0.531768 11.00000 0.04786 0.07054 = 0.07841 -0.00490 0.00179 0.02339 N1 4 0.543525 0.776145 0.594886 11.00000 0.03912 0.04808 = 0.03176 -0.00586 -0.00303 0.00255 C17 1 0.299131 0.821692 0.508422 11.00000 0.03621 0.03363 = 0.02913 -0.00338 0.00475 -0.00179 C16 1 0.556393 0.904936 0.395801 11.00000 0.04005 0.04006 = 0.04599 -0.00250 0.00246 -0.00080 C14 1 0.772690 0.904804 0.284240 11.00000 0.04617 0.07061 = 0.04544 0.02079 0.00240 -0.01370 AFIX 43 H14 2 0.846282 0.933570 0.246976 11.00000 -1.20000 AFIX 0 C13 1 0.769615 0.819650 0.283816 11.00000 0.04916 0.07176 = 0.03331 -0.00384 0.00699 -0.00327 AFIX 43 H13 2 0.840360 0.790511 0.245910 11.00000 -1.20000 AFIX 0 C12 1 0.661491 0.776597 0.339651 11.00000 0.05161 0.04643 = 0.03596 -0.00483 0.00741 -0.00294 AFIX 43 H12 2 0.661818 0.718645 0.339346 11.00000 -1.20000 AFIX 0 C11 1 0.552681 0.818850 0.396042 11.00000 0.03436 0.03939 = 0.02649 -0.00182 -0.00182 -0.00474 C4 1 0.439976 0.769666 0.459327 11.00000 0.03137 0.03361 = 0.02899 -0.00279 0.00024 0.00197 C3 1 0.583336 0.746125 0.526226 11.00000 0.03247 0.03750 = 0.03049 -0.00019 -0.00058 0.00100 C2 1 0.904684 0.681587 0.599333 11.00000 0.03446 0.05709 = 0.04822 -0.00288 -0.00795 0.00141 AFIX 23 H2A 2 1.044719 0.683880 0.591876 11.00000 -1.20000 H2B 2 0.866881 0.730350 0.629574 11.00000 -1.20000 AFIX 0 C1 1 0.856291 0.605684 0.646033 11.00000 0.07946 0.05771 = 0.04793 0.00165 -0.00883 0.01599 C22 1 0.367945 0.822334 0.586150 11.00000 0.03727 0.04139 = 0.03247 -0.00651 0.00021 -0.00124 C21 1 0.267713 0.863147 0.645433 11.00000 0.05047 0.05556 = 0.03401 -0.00976 0.00456 -0.00028 AFIX 43 H21 2 0.314264 0.863458 0.697105 11.00000 -1.20000 AFIX 0 C20 1 0.095392 0.903767 0.625881 11.00000 0.04620 0.04945 = 0.05126 -0.01566 0.01492 -0.00029 AFIX 43 H20 2 0.024693 0.931841 0.664519 11.00000 -1.20000 AFIX 0 C19 1 0.030431 0.902099 0.549071 11.00000 0.03469 0.04251 = 0.05454 -0.00145 0.00781 0.00304 C18 1 0.126580 0.860554 0.488581 11.00000 0.03868 0.04187 = 0.03764 0.00096 0.00090 0.00095 AFIX 43 H18 2 0.077302 0.858984 0.437348 11.00000 -1.20000 AFIX 0 C15 1 0.666313 0.948020 0.340105 11.00000 0.04946 0.04805 = 0.06477 0.01380 0.00180 -0.00872 AFIX 43 H15 2 0.668167 1.005966 0.340490 11.00000 -1.20000 AFIX 0 C5 1 0.330206 0.694720 0.424839 11.00000 0.03040 0.03656 = 0.03424 -0.00880 0.00319 -0.00138 C10 1 0.238773 0.701643 0.352145 11.00000 0.05337 0.06250 = 0.04072 -0.00211 -0.00957 -0.01089 AFIX 43 H10 2 0.249804 0.750699 0.323195 11.00000 -1.20000 AFIX 0 C9 1 0.130698 0.635656 0.322298 11.00000 0.05875 0.08785 = 0.05254 -0.02475 -0.00802 -0.01758 AFIX 43 H9 2 0.071199 0.640640 0.273091 11.00000 -1.20000 AFIX 0 C8 1 0.110579 0.563062 0.364589 11.00000 0.05287 0.06451 = 0.08693 -0.03849 0.01063 -0.01722 AFIX 43 H8 2 0.037760 0.519124 0.344267 11.00000 -1.20000 AFIX 0 C7 1 0.198513 0.556031 0.436744 11.00000 0.05621 0.04156 = 0.08660 -0.01022 0.01195 -0.01174 AFIX 43 H7 2 0.184435 0.507089 0.465651 11.00000 -1.20000 AFIX 0 C6 1 0.309034 0.621167 0.467657 11.00000 0.04011 0.03930 = 0.05295 -0.00168 0.00432 0.00040 AFIX 43 H6 2 0.368547 0.615524 0.516797 11.00000 -1.20000 AFIX 0 H16 2 0.473630 0.929183 0.431352 11.00000 0.04857 HKLF 4 REM agml_368_0ma_a.res in Pca2(1) REM wR2 = 0.1112, GooF = S = 1.045, Restrained GooF = 1.045 for all data REM R1 = 0.0441 for 3446 Fo > 4sig(Fo) and 0.0496 for all 3786 data REM 257 parameters refined using 1 restraints END WGHT 0.0509 0.2850 REM Instructions for potential hydrogen bonds HTAB C2 N1 REM Highest difference peak 0.213, deepest hole -0.246, 1-sigma level 0.044 Q1 1 0.9297 0.6811 0.5158 11.00000 0.05 0.21 ; _shelx_res_checksum 67537 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.78892(13) 0.68610(5) 0.50428(5) 0.0432(2) Uani 1 1 d . . . . . F2 F 0.6675(6) 0.5999(2) 0.6621(2) 0.0975(11) Uani 1 1 d . . . . . F3 F 0.9029(6) 0.53571(17) 0.60886(18) 0.0979(12) Uani 1 1 d . . . . . F1 F 0.9483(8) 0.6050(2) 0.7143(2) 0.1200(16) Uani 1 1 d . . . . . F4 F -0.1382(4) 0.94170(16) 0.53177(16) 0.0656(7) Uani 1 1 d . . . . . N1 N 0.5435(4) 0.77614(19) 0.59489(15) 0.0397(7) Uani 1 1 d . . . . . C17 C 0.2991(5) 0.82169(17) 0.5084(2) 0.0330(6) Uani 1 1 d . . . . . C16 C 0.5564(6) 0.9049(2) 0.3958(2) 0.0420(8) Uani 1 1 d . . . . . C14 C 0.7727(6) 0.9048(3) 0.2842(2) 0.0541(10) Uani 1 1 d . . . . . H14 H 0.846282 0.933570 0.246976 0.065 Uiso 1 1 calc R U . . . C13 C 0.7696(6) 0.8197(3) 0.2838(2) 0.0514(10) Uani 1 1 d . . . . . H13 H 0.840360 0.790511 0.245910 0.062 Uiso 1 1 calc R U . . . C12 C 0.6615(6) 0.7766(2) 0.3397(2) 0.0447(8) Uani 1 1 d . . . . . H12 H 0.661818 0.718645 0.339346 0.054 Uiso 1 1 calc R U . . . C11 C 0.5527(5) 0.81885(19) 0.39604(18) 0.0334(7) Uani 1 1 d . . . . . C4 C 0.4400(5) 0.76967(18) 0.45933(17) 0.0313(6) Uani 1 1 d . . . . . C3 C 0.5833(5) 0.74613(19) 0.52623(17) 0.0335(7) Uani 1 1 d . . . . . C2 C 0.9047(6) 0.6816(2) 0.5993(2) 0.0466(9) Uani 1 1 d . . . . . H2A H 1.044719 0.683880 0.591876 0.056 Uiso 1 1 calc R U . . . H2B H 0.866881 0.730350 0.629574 0.056 Uiso 1 1 calc R U . . . C1 C 0.8563(8) 0.6057(3) 0.6460(3) 0.0617(12) Uani 1 1 d . . . . . C22 C 0.3679(6) 0.8223(2) 0.58615(19) 0.0370(7) Uani 1 1 d . . . . . C21 C 0.2677(6) 0.8631(2) 0.6454(2) 0.0467(9) Uani 1 1 d . . . . . H21 H 0.314264 0.863458 0.697105 0.056 Uiso 1 1 calc R U . . . C20 C 0.0954(6) 0.9038(2) 0.6259(2) 0.0490(9) Uani 1 1 d . . . . . H20 H 0.024693 0.931841 0.664519 0.059 Uiso 1 1 calc R U . . . C19 C 0.0304(6) 0.9021(2) 0.5491(2) 0.0439(8) Uani 1 1 d . . . . . C18 C 0.1266(5) 0.8606(2) 0.48858(19) 0.0394(8) Uani 1 1 d . . . . . H18 H 0.077302 0.858984 0.437348 0.047 Uiso 1 1 calc R U . . . C15 C 0.6663(7) 0.9480(3) 0.3401(3) 0.0541(10) Uani 1 1 d . . . . . H15 H 0.668167 1.005966 0.340490 0.065 Uiso 1 1 calc R U . . . C5 C 0.3302(5) 0.6947(2) 0.42484(18) 0.0337(7) Uani 1 1 d . . . . . C10 C 0.2388(7) 0.7016(3) 0.3521(2) 0.0522(10) Uani 1 1 d . . . . . H10 H 0.249804 0.750699 0.323195 0.063 Uiso 1 1 calc R U . . . C9 C 0.1307(7) 0.6357(3) 0.3223(3) 0.0664(13) Uani 1 1 d . . . . . H9 H 0.071199 0.640640 0.273091 0.080 Uiso 1 1 calc R U . . . C8 C 0.1106(7) 0.5631(3) 0.3646(3) 0.0681(14) Uani 1 1 d . . . . . H8 H 0.037760 0.519124 0.344267 0.082 Uiso 1 1 calc R U . . . C7 C 0.1985(7) 0.5560(3) 0.4367(3) 0.0615(12) Uani 1 1 d . . . . . H7 H 0.184435 0.507089 0.465651 0.074 Uiso 1 1 calc R U . . . C6 C 0.3090(5) 0.6212(2) 0.4677(2) 0.0441(8) Uani 1 1 d . . . . . H6 H 0.368547 0.615524 0.516797 0.053 Uiso 1 1 calc R U . . . H16 H 0.474(7) 0.929(2) 0.431(2) 0.049(11) Uiso 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 S1 0.0372(5) 0.0542(5) 0.0381(4) -0.0031(4) 0.0014(4) 0.0096(4) F2 0.102(3) 0.089(2) 0.102(2) 0.0226(18) 0.043(2) -0.005(2) F3 0.155(4) 0.0536(15) 0.0854(19) -0.0023(14) 0.001(2) 0.0341(19) F1 0.194(5) 0.101(2) 0.0649(17) 0.0171(16) -0.056(2) 0.005(3) F4 0.0479(14) 0.0705(15) 0.0784(16) -0.0049(13) 0.0018(13) 0.0234(13) N1 0.0391(17) 0.0481(16) 0.0318(13) -0.0059(11) -0.0030(11) 0.0025(13) C17 0.0362(17) 0.0336(14) 0.0291(13) -0.0034(12) 0.0047(14) -0.0018(12) C16 0.040(2) 0.0401(17) 0.0460(18) -0.0025(15) 0.0025(16) -0.0008(16) C14 0.046(2) 0.071(3) 0.0454(19) 0.0208(19) 0.0024(17) -0.014(2) C13 0.049(2) 0.072(3) 0.0333(16) -0.0038(17) 0.0070(16) -0.0033(19) C12 0.052(2) 0.0464(19) 0.0360(16) -0.0048(14) 0.0074(16) -0.0029(17) C11 0.0344(18) 0.0394(16) 0.0265(13) -0.0018(12) -0.0018(12) -0.0047(14) C4 0.0314(17) 0.0336(14) 0.0290(14) -0.0028(11) 0.0002(12) 0.0020(13) C3 0.0325(16) 0.0375(15) 0.0305(15) -0.0002(12) -0.0006(12) 0.0010(13) C2 0.0345(19) 0.057(2) 0.0482(19) -0.0029(15) -0.0080(16) 0.0014(16) C1 0.079(4) 0.058(2) 0.048(2) 0.0016(18) -0.009(2) 0.016(2) C22 0.037(2) 0.0414(17) 0.0325(15) -0.0065(13) 0.0002(13) -0.0012(15) C21 0.050(2) 0.056(2) 0.0340(16) -0.0098(15) 0.0046(15) -0.0003(18) C20 0.046(2) 0.0494(19) 0.051(2) -0.0157(16) 0.0149(17) -0.0003(18) C19 0.035(2) 0.0425(18) 0.055(2) -0.0014(15) 0.0078(16) 0.0030(16) C18 0.0387(19) 0.0419(18) 0.0376(17) 0.0010(12) 0.0009(13) 0.0009(14) C15 0.049(2) 0.048(2) 0.065(2) 0.0138(18) 0.0018(19) -0.0087(18) C5 0.0304(17) 0.0366(16) 0.0342(14) -0.0088(12) 0.0032(13) -0.0014(13) C10 0.053(2) 0.063(2) 0.0407(19) -0.0021(17) -0.0096(16) -0.011(2) C9 0.059(3) 0.088(3) 0.053(2) -0.025(2) -0.0080(19) -0.018(3) C8 0.053(3) 0.065(3) 0.087(3) -0.038(2) 0.011(2) -0.017(2) C7 0.056(3) 0.042(2) 0.087(3) -0.010(2) 0.012(2) -0.0117(18) C6 0.040(2) 0.0393(18) 0.0529(19) -0.0017(15) 0.0043(16) 0.0004(16) 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' N N 0.0061 0.0033 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 S1 C2 100.93(16) . . ? C3 N1 C22 106.4(3) . . ? C22 C17 C4 107.6(3) . . ? C18 C17 C4 131.3(3) . . ? C18 C17 C22 121.0(3) . . ? C11 C16 C15 120.6(4) . . ? C11 C16 H16 114(3) . . ? C15 C16 H16 125(3) . . ? C13 C14 H14 120.1 . . ? C13 C14 C15 119.8(3) . . ? C15 C14 H14 120.1 . . ? C14 C13 H13 119.9 . . ? C14 C13 C12 120.2(4) . . ? C12 C13 H13 119.9 . . ? C13 C12 H12 119.6 . . ? C13 C12 C11 120.8(3) . . ? C11 C12 H12 119.6 . . ? C16 C11 C12 118.5(3) . . ? C16 C11 C4 121.6(3) . . ? C12 C11 C4 119.8(3) . . ? C17 C4 C11 114.6(3) . . ? C17 C4 C3 98.0(2) . . ? C17 C4 C5 109.0(3) . . ? C11 C4 C3 108.3(3) . . ? C5 C4 C11 112.6(2) . . ? C5 C4 C3 113.5(3) . . ? N1 C3 S1 124.7(3) . . ? N1 C3 C4 115.7(3) . . ? C4 C3 S1 119.5(2) . . ? S1 C2 H2A 108.7 . . ? S1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C1 C2 S1 114.1(3) . . ? C1 C2 H2A 108.7 . . ? C1 C2 H2B 108.7 . . ? F2 C1 C2 112.6(4) . . ? F3 C1 F2 105.8(4) . . ? F3 C1 C2 112.8(4) . . ? F1 C1 F2 106.8(5) . . ? F1 C1 F3 107.0(4) . . ? F1 C1 C2 111.4(4) . . ? C17 C22 N1 112.4(3) . . ? C21 C22 N1 126.4(3) . . ? C21 C22 C17 121.2(3) . . ? C22 C21 H21 120.9 . . ? C22 C21 C20 118.3(3) . . ? C20 C21 H21 120.9 . . ? C21 C20 H20 120.3 . . ? C19 C20 C21 119.5(3) . . ? C19 C20 H20 120.3 . . ? F4 C19 C20 118.2(3) . . ? F4 C19 C18 118.3(3) . . ? C20 C19 C18 123.5(3) . . ? C17 C18 C19 116.5(3) . . ? C17 C18 H18 121.7 . . ? C19 C18 H18 121.7 . . ? C16 C15 H15 120.0 . . ? C14 C15 C16 120.0(4) . . ? C14 C15 H15 120.0 . . ? C10 C5 C4 119.8(3) . . ? C10 C5 C6 118.8(3) . . ? C6 C5 C4 121.2(3) . . ? C5 C10 H10 119.9 . . ? C5 C10 C9 120.2(4) . . ? C9 C10 H10 119.9 . . ? C10 C9 H9 119.6 . . ? C8 C9 C10 120.8(4) . . ? C8 C9 H9 119.6 . . ? C9 C8 H8 120.3 . . ? C7 C8 C9 119.4(4) . . ? C7 C8 H8 120.3 . . ? C8 C7 H7 119.5 . . ? C8 C7 C6 120.9(4) . . ? C6 C7 H7 119.5 . . ? C5 C6 C7 119.9(4) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? 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 C3 1.748(3) . ? S1 C2 1.794(4) . ? F2 C1 1.327(6) . ? F3 C1 1.326(5) . ? F1 C1 1.316(5) . ? F4 C19 1.353(5) . ? N1 C3 1.286(4) . ? N1 C22 1.422(5) . ? C17 C4 1.523(4) . ? C17 C22 1.396(5) . ? C17 C18 1.380(5) . ? C16 C11 1.382(5) . ? C16 C15 1.390(5) . ? C16 H16 0.91(4) . ? C14 H14 0.9300 . ? C14 C13 1.367(6) . ? C14 C15 1.380(6) . ? C13 H13 0.9300 . ? C13 C12 1.385(5) . ? C12 H12 0.9300 . ? C12 C11 1.388(5) . ? C11 C4 1.538(4) . ? C4 C3 1.546(4) . ? C4 C5 1.534(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2 C1 1.489(6) . ? C22 C21 1.381(5) . ? C21 H21 0.9300 . ? C21 C20 1.390(6) . ? C20 H20 0.9300 . ? C20 C19 1.373(5) . ? C19 C18 1.388(5) . ? C18 H18 0.9300 . ? C15 H15 0.9300 . ? C5 C10 1.384(5) . ? C5 C6 1.392(5) . ? C10 H10 0.9300 . ? C10 C9 1.388(6) . ? C9 H9 0.9300 . ? C9 C8 1.374(8) . ? C8 H8 0.9300 . ? C8 C7 1.365(7) . ? C7 H7 0.9300 . ? C7 C6 1.393(5) . ? C6 H6 0.9300 . ? 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 S1 C2 C1 F2 -61.4(5) . . . . ? S1 C2 C1 F3 58.3(5) . . . . ? S1 C2 C1 F1 178.7(4) . . . . ? F4 C19 C18 C17 179.3(3) . . . . ? N1 C22 C21 C20 -178.6(3) . . . . ? C17 C4 C3 S1 -178.3(2) . . . . ? C17 C4 C3 N1 -1.0(4) . . . . ? C17 C4 C5 C10 89.3(4) . . . . ? C17 C4 C5 C6 -86.2(4) . . . . ? C17 C22 C21 C20 0.1(5) . . . . ? C16 C11 C4 C17 13.3(5) . . . . ? C16 C11 C4 C3 -95.0(4) . . . . ? C16 C11 C4 C5 138.6(3) . . . . ? C14 C13 C12 C11 0.9(6) . . . . ? C13 C14 C15 C16 0.0(7) . . . . ? C13 C12 C11 C16 -0.7(6) . . . . ? C13 C12 C11 C4 -177.7(3) . . . . ? C12 C11 C4 C17 -169.8(3) . . . . ? C12 C11 C4 C3 81.9(4) . . . . ? C12 C11 C4 C5 -44.5(4) . . . . ? C11 C16 C15 C14 0.2(6) . . . . ? C11 C4 C3 S1 -59.0(3) . . . . ? C11 C4 C3 N1 118.3(3) . . . . ? C11 C4 C5 C10 -39.1(4) . . . . ? C11 C4 C5 C6 145.4(3) . . . . ? C4 C17 C22 N1 0.4(4) . . . . ? C4 C17 C22 C21 -178.4(3) . . . . ? C4 C17 C18 C19 178.6(3) . . . . ? C4 C5 C10 C9 -176.7(4) . . . . ? C4 C5 C6 C7 176.1(3) . . . . ? C3 S1 C2 C1 95.2(3) . . . . ? C3 N1 C22 C17 -1.1(4) . . . . ? C3 N1 C22 C21 177.7(4) . . . . ? C3 C4 C5 C10 -162.6(3) . . . . ? C3 C4 C5 C6 21.8(4) . . . . ? C2 S1 C3 N1 0.6(3) . . . . ? C2 S1 C3 C4 177.7(2) . . . . ? C22 N1 C3 S1 178.4(2) . . . . ? C22 N1 C3 C4 1.3(4) . . . . ? C22 C17 C4 C11 -114.2(3) . . . . ? C22 C17 C4 C3 0.3(3) . . . . ? C22 C17 C4 C5 118.6(3) . . . . ? C22 C17 C18 C19 2.1(5) . . . . ? C22 C21 C20 C19 0.1(6) . . . . ? C21 C20 C19 F4 179.6(3) . . . . ? C21 C20 C19 C18 0.9(6) . . . . ? C20 C19 C18 C17 -2.0(5) . . . . ? C18 C17 C4 C11 69.0(4) . . . . ? C18 C17 C4 C3 -176.6(3) . . . . ? C18 C17 C4 C5 -58.2(4) . . . . ? C18 C17 C22 N1 177.6(3) . . . . ? C18 C17 C22 C21 -1.2(5) . . . . ? C15 C16 C11 C12 0.2(6) . . . . ? C15 C16 C11 C4 177.1(3) . . . . ? C15 C14 C13 C12 -0.6(7) . . . . ? C5 C4 C3 S1 66.9(3) . . . . ? C5 C4 C3 N1 -115.8(3) . . . . ? C5 C10 C9 C8 0.8(7) . . . . ? C10 C5 C6 C7 0.5(5) . . . . ? C10 C9 C8 C7 -0.1(8) . . . . ? C9 C8 C7 C6 -0.4(7) . . . . ? C8 C7 C6 C5 0.2(6) . . . . ? C6 C5 C10 C9 -1.0(6) . . . . ?