#------------------------------------------------------------------------------ #$Date: 2023-11-24 02:38:02 +0200 (Fri, 24 Nov 2023) $ #$Revision: 287767 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247789.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_7247789 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 'C23 H18 F3 N S' _chemical_formula_sum 'C23 H18 F3 N S' _chemical_formula_weight 397.44 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _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 8 _cell_length_a 7.0705(6) _cell_length_b 16.8461(16) _cell_length_c 32.575(3) _cell_measurement_reflns_used 9789 _cell_measurement_temperature 298 _cell_measurement_theta_max 26.41 _cell_measurement_theta_min 2.42 _cell_volume 3880.0(6) _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 2019/1 (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 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w 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 0.0511 _diffrn_reflns_av_unetI/netI 0.0206 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_number 55828 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.413 _diffrn_reflns_theta_min 2.722 _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 0.202 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1667 before and 0.0769 after correction. The Ratio of minimum to maximum transmission is 0.8213. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.361 _exptl_crystal_description block _exptl_crystal_F_000 1648 _exptl_crystal_size_max 0.235 _exptl_crystal_size_mid 0.156 _exptl_crystal_size_min 0.123 _refine_diff_density_max 0.227 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 254 _refine_ls_number_reflns 3971 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.151 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0507 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+2.1881P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1272 _refine_ls_wR_factor_ref 0.1296 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3623 _reflns_number_total 3971 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03702a2.cif _cod_data_source_block agml_867_0m_a _cod_original_cell_volume 3880.1(6) _cod_database_code 7247789 _shelx_shelxl_version_number 2019/1 _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. ; _olex2_refinement_description ; 1.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B) 1.b Aromatic/amide H refined with riding coordinates: C18(H18), C12(H12), C16(H16), C6(H6), C21(H21), C22(H22), C15(H15), C14(H14), C13(H13), C10(H10), C7(H7), C8(H8), C9(H9) 1.c Idealised Me refined as rotating group: C20(H20A,H20B,H20C) ; _shelx_res_file ; TITL agml_867_0m_a_a.res in Pbca agml_867_0m_a.res created by SHELXL-2019/1 at 11:22:50 on 19-Apr-2023 REM Old TITL AGML_867_0m_a.res in Pbca REM SHELXT solution in Pbca: R1 0.154, Rweak 0.012, Alpha 0.034 REM 1.354 for 556 systematic absences, Orientation as input REM Formula found by SHELXT: C23 F3 N S CELL 0.71073 7.0705 16.8461 32.5754 90 90 90 ZERR 8 0.0006 0.0016 0.0025 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H F N S UNIT 184 144 24 8 8 L.S. 10 PLAN 2 0 0 TEMP 0 CONF list 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.050500 2.188100 FVAR 0.54890 S1 5 0.217441 0.428755 0.340335 11.00000 0.04060 0.04279 = 0.05755 0.00415 -0.01306 0.00182 N1 4 0.453937 0.338147 0.384379 11.00000 0.03725 0.03288 = 0.04813 0.00291 -0.00500 -0.00210 F2 3 0.098088 0.320713 0.267838 11.00000 0.15131 0.09071 = 0.05984 0.00422 -0.03651 -0.00356 F1 3 0.327801 0.267976 0.299267 11.00000 0.10154 0.11125 = 0.09695 -0.02910 0.00233 0.03820 C17 1 0.695471 0.422709 0.406738 11.00000 0.03338 0.03038 = 0.03564 0.00073 0.00276 0.00252 C4 1 0.561744 0.473484 0.380881 11.00000 0.03379 0.03097 = 0.03580 0.00153 0.00002 0.00012 C23 1 0.624901 0.345529 0.407096 11.00000 0.03529 0.03161 = 0.04007 0.00019 -0.00069 0.00073 C11 1 0.458783 0.539366 0.404631 11.00000 0.03539 0.02612 = 0.04133 0.00295 0.00414 -0.00290 C5 1 0.669352 0.506213 0.343575 11.00000 0.03322 0.04054 = 0.03956 0.00852 0.00100 0.00438 C3 1 0.418258 0.407085 0.369709 11.00000 0.03296 0.03465 = 0.03666 -0.00002 -0.00118 -0.00005 C18 1 0.862551 0.440604 0.426713 11.00000 0.03403 0.03897 = 0.04225 0.00031 0.00289 -0.00367 AFIX 43 H18 2 0.911527 0.491815 0.425873 11.00000 -1.20000 AFIX 0 F3 3 0.052723 0.217068 0.303405 11.00000 0.18845 0.07134 = 0.10751 -0.01035 -0.01722 -0.05684 C12 1 0.336291 0.589982 0.383663 11.00000 0.05050 0.03716 = 0.04569 0.00388 0.00037 0.00591 AFIX 43 H12 2 0.323795 0.585293 0.355346 11.00000 -1.20000 AFIX 0 C16 1 0.477855 0.549225 0.446709 11.00000 0.04140 0.03388 = 0.04336 0.00128 0.00082 0.00014 AFIX 43 H16 2 0.560866 0.516865 0.461213 11.00000 -1.20000 AFIX 0 C6 1 0.696462 0.460274 0.308617 11.00000 0.04261 0.05853 = 0.04002 0.00257 0.00072 0.00476 AFIX 43 H6 2 0.641070 0.410325 0.306805 11.00000 -1.20000 AFIX 0 C19 1 0.957146 0.380558 0.448246 11.00000 0.02927 0.05135 = 0.04164 -0.00040 0.00252 0.00388 C21 1 0.884085 0.304043 0.447952 11.00000 0.04115 0.04300 = 0.05008 0.00479 -0.00038 0.01314 AFIX 43 H21 2 0.948399 0.264144 0.461896 11.00000 -1.20000 AFIX 0 C22 1 0.718235 0.285442 0.427494 11.00000 0.04715 0.03092 = 0.05304 0.00297 -0.00179 0.00399 AFIX 43 H22 2 0.671134 0.233897 0.427511 11.00000 -1.20000 AFIX 0 C15 1 0.374987 0.606589 0.467411 11.00000 0.05463 0.04257 = 0.04760 -0.00603 0.00606 -0.00052 AFIX 43 H15 2 0.389342 0.612407 0.495630 11.00000 -1.20000 AFIX 0 C14 1 0.251189 0.655198 0.446357 11.00000 0.04935 0.03675 = 0.06471 -0.00749 0.01220 0.00379 AFIX 43 H14 2 0.180556 0.693113 0.460342 11.00000 -1.20000 AFIX 0 C13 1 0.233189 0.647019 0.404365 11.00000 0.04807 0.03691 = 0.06732 0.00535 0.00069 0.01044 AFIX 43 H13 2 0.151325 0.680039 0.389951 11.00000 -1.20000 AFIX 0 C2 1 0.101820 0.333733 0.339493 11.00000 0.03602 0.05505 = 0.05987 0.00311 -0.00677 -0.00830 AFIX 23 H2A 2 0.138822 0.304147 0.363743 11.00000 -1.20000 H2B 2 -0.033841 0.341917 0.340810 11.00000 -1.20000 AFIX 0 C20 1 1.135980 0.398673 0.471733 11.00000 0.03833 0.07278 = 0.06830 0.00727 -0.00947 -0.00077 AFIX 137 H20A 2 1.222470 0.426799 0.454283 11.00000 -1.50000 H20B 2 1.193121 0.349947 0.480662 11.00000 -1.50000 H20C 2 1.106115 0.430796 0.495196 11.00000 -1.50000 AFIX 0 C10 1 0.754364 0.580365 0.345583 11.00000 0.05642 0.04824 = 0.06267 0.00668 0.01239 -0.00808 AFIX 43 H10 2 0.738943 0.611603 0.368882 11.00000 -1.20000 AFIX 0 C7 1 0.806059 0.488664 0.276331 11.00000 0.05160 0.09804 = 0.04132 0.00836 0.00733 0.01086 AFIX 43 H7 2 0.824205 0.457379 0.253141 11.00000 -1.20000 AFIX 0 C1 1 0.146256 0.285517 0.302494 11.00000 0.07916 0.04942 = 0.05978 0.00196 -0.01613 -0.00646 C8 1 0.887244 0.562152 0.278429 11.00000 0.04942 0.09419 = 0.06498 0.03485 0.01665 0.00894 AFIX 43 H8 2 0.959087 0.581057 0.256605 11.00000 -1.20000 AFIX 0 C9 1 0.862332 0.608201 0.313004 11.00000 0.05955 0.06111 = 0.09591 0.02469 0.02038 -0.00981 AFIX 43 H9 2 0.918074 0.658119 0.314515 11.00000 -1.20000 AFIX 0 HKLF 4 REM agml_867_0m_a_a.res in Pbca REM wR2 = 0.1296, GooF = S = 1.151, Restrained GooF = 1.151 for all data REM R1 = 0.0507 for 3623 Fo > 4sig(Fo) and 0.0553 for all 3971 data REM 254 parameters refined using 0 restraints END WGHT 0.0505 2.1882 REM Highest difference peak 0.227, deepest hole -0.269, 1-sigma level 0.044 Q1 1 0.2680 0.2992 0.2808 11.00000 0.05 0.23 Q2 1 1.2548 0.3739 0.4585 11.00000 0.05 0.22 ; _shelx_res_checksum 4669 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_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' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, 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 0.21744(8) 0.42876(3) 0.34034(2) 0.04698(17) Uani 1 1 d . . . . . N1 N 0.4539(2) 0.33815(9) 0.38438(5) 0.0394(4) Uani 1 1 d . . . . . F2 F 0.0981(4) 0.32071(11) 0.26784(5) 0.1006(7) Uani 1 1 d . . . . . F1 F 0.3278(3) 0.26798(13) 0.29927(7) 0.1032(7) Uani 1 1 d . . . . . C17 C 0.6955(3) 0.42271(10) 0.40674(6) 0.0331(4) Uani 1 1 d . . . . . C4 C 0.5617(3) 0.47348(11) 0.38088(6) 0.0335(4) Uani 1 1 d . . . . . C23 C 0.6249(3) 0.34553(11) 0.40710(6) 0.0357(4) Uani 1 1 d . . . . . C11 C 0.4588(3) 0.53937(10) 0.40463(6) 0.0343(4) Uani 1 1 d . . . . . C5 C 0.6694(3) 0.50621(12) 0.34358(6) 0.0378(4) Uani 1 1 d . . . . . C3 C 0.4183(3) 0.40708(11) 0.36971(6) 0.0348(4) Uani 1 1 d . . . . . C18 C 0.8626(3) 0.44060(12) 0.42671(6) 0.0384(4) Uani 1 1 d . . . . . H18 H 0.911527 0.491815 0.425873 0.046 Uiso 1 1 calc R U . . . F3 F 0.0527(4) 0.21707(11) 0.30340(7) 0.1224(9) Uani 1 1 d . . . . . C12 C 0.3363(3) 0.58998(12) 0.38366(7) 0.0445(5) Uani 1 1 d . . . . . H12 H 0.323795 0.585293 0.355346 0.053 Uiso 1 1 calc R U . . . C16 C 0.4779(3) 0.54923(11) 0.44671(6) 0.0395(4) Uani 1 1 d . . . . . H16 H 0.560866 0.516865 0.461213 0.047 Uiso 1 1 calc R U . . . C6 C 0.6965(3) 0.46027(14) 0.30862(6) 0.0471(5) Uani 1 1 d . . . . . H6 H 0.641070 0.410325 0.306805 0.056 Uiso 1 1 calc R U . . . C19 C 0.9571(3) 0.38056(13) 0.44825(6) 0.0408(4) Uani 1 1 d . . . . . C21 C 0.8841(3) 0.30404(12) 0.44795(7) 0.0447(5) Uani 1 1 d . . . . . H21 H 0.948399 0.264144 0.461896 0.054 Uiso 1 1 calc R U . . . C22 C 0.7182(3) 0.28544(12) 0.42749(7) 0.0437(5) Uani 1 1 d . . . . . H22 H 0.671134 0.233897 0.427511 0.052 Uiso 1 1 calc R U . . . C15 C 0.3750(3) 0.60659(13) 0.46741(7) 0.0483(5) Uani 1 1 d . . . . . H15 H 0.389342 0.612407 0.495630 0.058 Uiso 1 1 calc R U . . . C14 C 0.2512(3) 0.65520(13) 0.44636(8) 0.0503(5) Uani 1 1 d . . . . . H14 H 0.180556 0.693113 0.460342 0.060 Uiso 1 1 calc R U . . . C13 C 0.2332(3) 0.64702(13) 0.40436(8) 0.0508(5) Uani 1 1 d . . . . . H13 H 0.151325 0.680039 0.389951 0.061 Uiso 1 1 calc R U . . . C2 C 0.1018(3) 0.33373(14) 0.33949(7) 0.0503(5) Uani 1 1 d . . . . . H2A H 0.138822 0.304147 0.363743 0.060 Uiso 1 1 calc R U . . . H2B H -0.033841 0.341917 0.340810 0.060 Uiso 1 1 calc R U . . . C20 C 1.1360(3) 0.39867(16) 0.47173(8) 0.0598(6) Uani 1 1 d . . . . . H20A H 1.222470 0.426799 0.454283 0.090 Uiso 1 1 calc R U . . . H20B H 1.193121 0.349947 0.480662 0.090 Uiso 1 1 calc R U . . . H20C H 1.106115 0.430796 0.495196 0.090 Uiso 1 1 calc R U . . . C10 C 0.7544(4) 0.58036(14) 0.34558(8) 0.0558(6) Uani 1 1 d . . . . . H10 H 0.738943 0.611603 0.368882 0.067 Uiso 1 1 calc R U . . . C7 C 0.8061(4) 0.48866(19) 0.27633(7) 0.0636(7) Uani 1 1 d . . . . . H7 H 0.824205 0.457379 0.253141 0.076 Uiso 1 1 calc R U . . . C1 C 0.1463(4) 0.28552(15) 0.30249(8) 0.0628(7) Uani 1 1 d . . . . . C8 C 0.8872(4) 0.56215(19) 0.27843(9) 0.0695(8) Uani 1 1 d . . . . . H8 H 0.959087 0.581057 0.256605 0.083 Uiso 1 1 calc R U . . . C9 C 0.8623(4) 0.60820(17) 0.31300(10) 0.0722(8) Uani 1 1 d . . . . . H9 H 0.918074 0.658119 0.314515 0.087 Uiso 1 1 calc R U . . . 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 0.0406(3) 0.0428(3) 0.0575(3) 0.0041(2) -0.0131(2) 0.0018(2) N1 0.0372(9) 0.0329(8) 0.0481(9) 0.0029(7) -0.0050(7) -0.0021(7) F2 0.1513(19) 0.0907(13) 0.0598(10) 0.0042(9) -0.0365(12) -0.0036(13) F1 0.1015(15) 0.1112(16) 0.0970(14) -0.0291(12) 0.0023(11) 0.0382(13) C17 0.0334(9) 0.0304(9) 0.0356(9) 0.0007(7) 0.0028(7) 0.0025(7) C4 0.0338(9) 0.0310(9) 0.0358(9) 0.0015(7) 0.0000(8) 0.0001(7) C23 0.0353(10) 0.0316(9) 0.0401(10) 0.0002(7) -0.0007(8) 0.0007(8) C11 0.0354(10) 0.0261(8) 0.0413(10) 0.0030(7) 0.0041(8) -0.0029(7) C5 0.0332(9) 0.0405(10) 0.0396(10) 0.0085(8) 0.0010(8) 0.0044(8) C3 0.0330(9) 0.0347(9) 0.0367(9) 0.0000(7) -0.0012(8) 0.0000(7) C18 0.0340(10) 0.0390(10) 0.0423(10) 0.0003(8) 0.0029(8) -0.0037(8) F3 0.188(3) 0.0713(12) 0.1075(15) -0.0103(11) -0.0172(16) -0.0568(14) C12 0.0505(12) 0.0372(10) 0.0457(11) 0.0039(8) 0.0004(9) 0.0059(9) C16 0.0414(10) 0.0339(9) 0.0434(10) 0.0013(8) 0.0008(9) 0.0001(8) C6 0.0426(12) 0.0585(13) 0.0400(11) 0.0026(9) 0.0007(9) 0.0048(10) C19 0.0293(9) 0.0513(12) 0.0416(10) -0.0004(9) 0.0025(8) 0.0039(8) C21 0.0411(11) 0.0430(11) 0.0501(12) 0.0048(9) -0.0004(9) 0.0131(9) C22 0.0471(12) 0.0309(9) 0.0530(12) 0.0030(8) -0.0018(9) 0.0040(8) C15 0.0546(13) 0.0426(11) 0.0476(11) -0.0060(9) 0.0061(10) -0.0005(10) C14 0.0494(12) 0.0368(10) 0.0647(14) -0.0075(10) 0.0122(11) 0.0038(9) C13 0.0481(12) 0.0369(11) 0.0673(14) 0.0054(10) 0.0007(11) 0.0104(9) C2 0.0360(10) 0.0551(13) 0.0599(13) 0.0031(10) -0.0068(10) -0.0083(10) C20 0.0383(12) 0.0728(16) 0.0683(15) 0.0073(13) -0.0095(11) -0.0008(11) C10 0.0564(14) 0.0482(13) 0.0627(14) 0.0067(11) 0.0124(11) -0.0081(11) C7 0.0516(14) 0.098(2) 0.0413(12) 0.0084(13) 0.0073(10) 0.0109(14) C1 0.0792(19) 0.0494(13) 0.0598(15) 0.0020(11) -0.0161(13) -0.0065(13) C8 0.0494(14) 0.094(2) 0.0650(16) 0.0348(15) 0.0166(12) 0.0089(14) C9 0.0596(16) 0.0611(16) 0.096(2) 0.0247(15) 0.0204(15) -0.0098(13) 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 101.04(10) . . ? C3 N1 C23 106.39(16) . . ? C23 C17 C4 107.79(16) . . ? C18 C17 C4 131.79(17) . . ? C18 C17 C23 120.40(17) . . ? C17 C4 C11 114.83(15) . . ? C17 C4 C5 109.30(15) . . ? C17 C4 C3 97.48(14) . . ? C11 C4 C3 109.19(15) . . ? C5 C4 C11 111.95(15) . . ? C5 C4 C3 113.36(15) . . ? C17 C23 N1 112.44(16) . . ? C22 C23 N1 126.37(18) . . ? C22 C23 C17 121.19(18) . . ? C12 C11 C4 119.31(17) . . ? C16 C11 C4 122.55(17) . . ? C16 C11 C12 118.11(18) . . ? C6 C5 C4 121.10(18) . . ? C10 C5 C4 120.02(19) . . ? C10 C5 C6 118.7(2) . . ? N1 C3 S1 123.55(15) . . ? N1 C3 C4 115.90(16) . . ? C4 C3 S1 120.50(13) . . ? C17 C18 H18 120.4 . . ? C17 C18 C19 119.10(18) . . ? C19 C18 H18 120.4 . . ? C11 C12 H12 119.5 . . ? C13 C12 C11 120.9(2) . . ? C13 C12 H12 119.5 . . ? C11 C16 H16 119.5 . . ? C15 C16 C11 120.91(19) . . ? C15 C16 H16 119.5 . . ? C5 C6 H6 119.8 . . ? C5 C6 C7 120.3(2) . . ? C7 C6 H6 119.8 . . ? C18 C19 C20 120.5(2) . . ? C21 C19 C18 119.29(18) . . ? C21 C19 C20 120.19(19) . . ? C19 C21 H21 119.1 . . ? C22 C21 C19 121.90(19) . . ? C22 C21 H21 119.1 . . ? C23 C22 C21 118.10(19) . . ? C23 C22 H22 120.9 . . ? C21 C22 H22 120.9 . . ? C16 C15 H15 119.8 . . ? C14 C15 C16 120.3(2) . . ? C14 C15 H15 119.8 . . ? C15 C14 H14 120.3 . . ? C15 C14 C13 119.4(2) . . ? C13 C14 H14 120.3 . . ? C12 C13 H13 119.9 . . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 119.9 . . ? S1 C2 H2A 108.8 . . ? S1 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C1 C2 S1 113.75(17) . . ? C1 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C5 C10 H10 119.8 . . ? C5 C10 C9 120.4(2) . . ? C9 C10 H10 119.8 . . ? C6 C7 H7 119.7 . . ? C8 C7 C6 120.5(3) . . ? C8 C7 H7 119.7 . . ? F2 C1 F1 106.4(3) . . ? F2 C1 F3 106.3(2) . . ? F2 C1 C2 113.2(2) . . ? F1 C1 F3 106.9(3) . . ? F1 C1 C2 113.1(2) . . ? F3 C1 C2 110.5(2) . . ? C7 C8 H8 120.1 . . ? C7 C8 C9 119.8(2) . . ? C9 C8 H8 120.1 . . ? C10 C9 H9 119.9 . . ? C8 C9 C10 120.3(3) . . ? C8 C9 H9 119.9 . . ? 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 1.7507(19) . ? S1 C2 1.798(2) . ? N1 C23 1.423(2) . ? N1 C3 1.281(2) . ? F2 C1 1.320(3) . ? F1 C1 1.321(3) . ? C17 C4 1.528(2) . ? C17 C23 1.393(3) . ? C17 C18 1.382(3) . ? C4 C11 1.536(2) . ? C4 C5 1.536(3) . ? C4 C3 1.553(3) . ? C23 C22 1.379(3) . ? C11 C12 1.394(3) . ? C11 C16 1.387(3) . ? C5 C6 1.390(3) . ? C5 C10 1.388(3) . ? C18 H18 0.9300 . ? C18 C19 1.401(3) . ? F3 C1 1.330(3) . ? C12 H12 0.9300 . ? C12 C13 1.382(3) . ? C16 H16 0.9300 . ? C16 C15 1.385(3) . ? C6 H6 0.9300 . ? C6 C7 1.391(3) . ? C19 C21 1.389(3) . ? C19 C20 1.509(3) . ? C21 H21 0.9300 . ? C21 C22 1.385(3) . ? C22 H22 0.9300 . ? C15 H15 0.9300 . ? C15 C14 1.381(3) . ? C14 H14 0.9300 . ? C14 C13 1.381(3) . ? C13 H13 0.9300 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2 C1 1.487(4) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C10 H10 0.9300 . ? C10 C9 1.389(3) . ? C7 H7 0.9300 . ? C7 C8 1.366(4) . ? C8 H8 0.9300 . ? C8 C9 1.379(4) . ? C9 H9 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 -59.4(3) . . . . ? S1 C2 C1 F1 61.7(3) . . . . ? S1 C2 C1 F3 -178.5(2) . . . . ? N1 C23 C22 C21 179.81(19) . . . . ? C17 C4 C11 C12 178.78(17) . . . . ? C17 C4 C11 C16 -3.4(3) . . . . ? C17 C4 C5 C6 81.7(2) . . . . ? C17 C4 C5 C10 -93.1(2) . . . . ? C17 C4 C3 S1 178.00(13) . . . . ? C17 C4 C3 N1 0.2(2) . . . . ? C17 C23 C22 C21 0.4(3) . . . . ? C17 C18 C19 C21 2.0(3) . . . . ? C17 C18 C19 C20 -177.68(19) . . . . ? C4 C17 C23 N1 -0.7(2) . . . . ? C4 C17 C23 C22 178.75(18) . . . . ? C4 C17 C18 C19 -179.48(18) . . . . ? C4 C11 C12 C13 176.33(19) . . . . ? C4 C11 C16 C15 -176.50(18) . . . . ? C4 C5 C6 C7 -175.25(19) . . . . ? C4 C5 C10 C9 175.8(2) . . . . ? C23 N1 C3 S1 -178.33(14) . . . . ? C23 N1 C3 C4 -0.6(2) . . . . ? C23 C17 C4 C11 115.51(17) . . . . ? C23 C17 C4 C5 -117.73(17) . . . . ? C23 C17 C4 C3 0.29(18) . . . . ? C23 C17 C18 C19 -1.7(3) . . . . ? C11 C4 C5 C6 -149.88(18) . . . . ? C11 C4 C5 C10 35.3(3) . . . . ? C11 C4 C3 S1 58.38(19) . . . . ? C11 C4 C3 N1 -119.38(18) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C11 C16 C15 C14 0.0(3) . . . . ? C5 C4 C11 C12 53.4(2) . . . . ? C5 C4 C11 C16 -128.76(19) . . . . ? C5 C4 C3 S1 -67.17(19) . . . . ? C5 C4 C3 N1 115.06(19) . . . . ? C5 C6 C7 C8 -0.5(4) . . . . ? C5 C10 C9 C8 -0.5(4) . . . . ? C3 S1 C2 C1 -95.15(19) . . . . ? C3 N1 C23 C17 0.8(2) . . . . ? C3 N1 C23 C22 -178.6(2) . . . . ? C3 C4 C11 C12 -73.0(2) . . . . ? C3 C4 C11 C16 104.9(2) . . . . ? C3 C4 C5 C6 -25.8(2) . . . . ? C3 C4 C5 C10 159.33(19) . . . . ? C18 C17 C4 C11 -66.5(3) . . . . ? C18 C17 C4 C5 60.2(3) . . . . ? C18 C17 C4 C3 178.3(2) . . . . ? C18 C17 C23 N1 -178.94(17) . . . . ? C18 C17 C23 C22 0.5(3) . . . . ? C18 C19 C21 C22 -1.1(3) . . . . ? C12 C11 C16 C15 1.4(3) . . . . ? C16 C11 C12 C13 -1.6(3) . . . . ? C16 C15 C14 C13 -1.1(3) . . . . ? C6 C5 C10 C9 0.8(4) . . . . ? C6 C7 C8 C9 0.8(4) . . . . ? C19 C21 C22 C23 -0.1(3) . . . . ? C15 C14 C13 C12 0.9(4) . . . . ? C2 S1 C3 N1 0.4(2) . . . . ? C2 S1 C3 C4 -177.18(15) . . . . ? C20 C19 C21 C22 178.6(2) . . . . ? C10 C5 C6 C7 -0.3(3) . . . . ? C7 C8 C9 C10 -0.3(4) . . . . ?