#------------------------------------------------------------------------------ #$Date: 2023-01-25 03:34:35 +0200 (Wed, 25 Jan 2023) $ #$Revision: 280571 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/91/7159116.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_7159116 loop_ _publ_author_name 'Patel, Bhisma K.' 'Sahoo, Ashish Kumar' 'Rakshit, Amitava' 'Pan, Avishek' 'Dhara, Hirendra Nath' _publ_section_title ; Visible/Solar-Light-Driven Thiyl-Radical-Triggered Synthesis of Multi-Substituted Pyridines ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D3OB00009E _journal_year 2023 _chemical_formula_sum 'C24 H15 F N2 S' _chemical_formula_weight 382.44 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2019/1 _audit_update_record ; 2022-08-17 deposited with the CCDC. 2023-01-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 109.3170(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.2258(5) _cell_length_b 8.0745(3) _cell_length_c 19.2139(8) _cell_measurement_reflns_used 9936 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 27.72 _cell_measurement_theta_min 2.25 _cell_volume 1936.37(13) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014 (Sheldrick 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 297(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_unetI/netI 0.0220 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 32809 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.050 _diffrn_reflns_theta_max 25.050 _diffrn_reflns_theta_min 2.246 _exptl_absorpt_coefficient_mu 0.188 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.312 _exptl_crystal_description Needle _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.29 _refine_diff_density_max 0.183 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.030 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 253 _refine_ls_number_reflns 3414 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0407 _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^)+(0.0486P)^2^+0.6826P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0973 _refine_ls_wR_factor_ref 0.1182 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2595 _reflns_number_total 3414 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ob00009e2.cif _cod_data_source_block 4-Fspart _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7159116 _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. ; _exptl_absorpt_special_details none _shelx_res_file ; TITL JBB_0ma_a.res in P2(1)/c JBB_0ma_a.res created by SHELXL-2019/1 at 21:09:30 on 16-Aug-2022 CELL 0.71073 13.2258 8.0745 19.2139 90 109.317 90 ZERR 4 0.0005 0.0003 0.0008 0 0.001 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C F N S H UNIT 96 4 8 4 60 OMIT -3 50.1 L.S. 40 ACTA BOND $H FMAP 2 PLAN 20 CONF MORE -1 TEMP 23.85 WGHT 0.048649 0.682633 FVAR 0.92511 S1 4 0.527914 0.662363 0.723376 11.00000 0.06850 0.07172 = 0.07564 -0.02575 0.01695 -0.00809 N1 3 0.548358 0.444551 0.623907 11.00000 0.05688 0.05127 = 0.06313 -0.00479 0.01895 -0.00613 F2 2 0.986875 0.698789 0.769598 11.00000 0.06966 0.23378 = 0.10270 -0.01767 0.02441 -0.01003 C2 1 0.367813 0.496660 0.619788 11.00000 0.05707 0.04432 = 0.05574 -0.00016 0.02023 -0.00368 C3 1 0.327610 0.392068 0.558733 11.00000 0.05467 0.04417 = 0.05414 0.00220 0.01911 -0.00557 N2 3 0.246402 0.656291 0.677081 11.00000 0.08183 0.06795 = 0.09270 -0.01933 0.03442 0.00157 C18 1 0.211626 0.356892 0.525005 11.00000 0.05248 0.04608 = 0.05626 -0.00303 0.01717 -0.00311 C5 1 0.510292 0.340950 0.565785 11.00000 0.05549 0.04280 = 0.05785 0.00043 0.02026 -0.00585 C1 1 0.479038 0.520357 0.649189 11.00000 0.06019 0.04736 = 0.05676 -0.00403 0.01711 -0.00506 C4 1 0.401459 0.317265 0.531775 11.00000 0.05730 0.04980 = 0.05506 -0.00647 0.02027 -0.00971 AFIX 43 H4 5 0.377464 0.250148 0.490196 11.00000 -1.20000 AFIX 0 C6 1 0.592169 0.252987 0.542925 11.00000 0.05701 0.04332 = 0.07041 0.00159 0.02760 -0.00569 C19 1 0.152364 0.305627 0.568040 11.00000 0.05642 0.07325 = 0.05920 0.00049 0.02012 -0.00758 AFIX 43 H19 5 0.184456 0.299400 0.618952 11.00000 -1.20000 AFIX 0 C12 1 0.665639 0.670137 0.733782 11.00000 0.06675 0.05697 = 0.05113 -0.01028 0.00660 -0.00786 C24 1 0.298609 0.585200 0.650727 11.00000 0.06193 0.04972 = 0.06597 -0.00639 0.01991 -0.00538 C11 1 0.567226 0.176720 0.474560 11.00000 0.07424 0.05270 = 0.07398 0.00107 0.03462 -0.00262 AFIX 43 H11 5 0.497326 0.180587 0.441959 11.00000 -1.20000 AFIX 0 C10 1 0.645398 0.094838 0.454350 11.00000 0.09558 0.05472 = 0.09261 -0.00478 0.05412 -0.00439 AFIX 43 H10 5 0.627812 0.044887 0.408255 11.00000 -1.20000 AFIX 0 C23 1 0.162092 0.366910 0.449528 11.00000 0.07023 0.08216 = 0.05832 -0.00180 0.02101 -0.01266 AFIX 43 H23 5 0.200937 0.400455 0.419549 11.00000 -1.20000 AFIX 0 C13 1 0.708744 0.811309 0.714697 11.00000 0.08030 0.06520 = 0.05701 -0.00007 0.00733 -0.00787 AFIX 43 H13 5 0.664673 0.900444 0.693704 11.00000 -1.20000 AFIX 0 C17 1 0.731863 0.538706 0.764292 11.00000 0.07878 0.06486 = 0.07324 -0.00162 0.01158 -0.00027 AFIX 43 H17 5 0.702922 0.443550 0.777458 11.00000 -1.20000 AFIX 0 C21 1 -0.002483 0.274931 0.462003 11.00000 0.05198 0.09633 = 0.08747 -0.00847 0.01238 -0.00908 AFIX 43 H21 5 -0.074446 0.247261 0.440891 11.00000 -1.20000 AFIX 0 C9 1 0.748447 0.087334 0.502102 11.00000 0.08281 0.06152 = 0.12968 0.00314 0.06492 0.00401 AFIX 43 H9 5 0.800940 0.033153 0.488332 11.00000 -1.20000 AFIX 0 C20 1 0.046074 0.263523 0.536391 11.00000 0.05711 0.09404 = 0.07882 -0.00173 0.02593 -0.01172 AFIX 43 H20 5 0.007247 0.227129 0.565927 11.00000 -1.20000 AFIX 0 C7 1 0.697029 0.243293 0.590514 11.00000 0.05794 0.07911 = 0.08974 -0.00951 0.02785 -0.00601 AFIX 43 H7 5 0.715597 0.293589 0.636581 11.00000 -1.20000 AFIX 0 C16 1 0.839332 0.545701 0.775549 11.00000 0.08348 0.09708 = 0.07111 -0.00404 0.00816 0.01782 AFIX 43 H16 5 0.883603 0.456049 0.795444 11.00000 -1.20000 AFIX 0 C22 1 0.054603 0.327010 0.418503 11.00000 0.07262 0.10388 = 0.06176 -0.00421 0.00502 -0.01000 AFIX 43 H22 5 0.021183 0.335755 0.367789 11.00000 -1.20000 AFIX 0 C15 1 0.879626 0.686594 0.756972 11.00000 0.06226 0.14030 = 0.05745 -0.01143 0.01013 0.00139 C8 1 0.774025 0.159942 0.570288 11.00000 0.06137 0.09176 = 0.11957 -0.00282 0.03553 0.00140 AFIX 43 H8 5 0.843686 0.152936 0.603076 11.00000 -1.20000 AFIX 0 C14 1 0.817963 0.820341 0.726830 11.00000 0.08559 0.11062 = 0.06472 -0.00312 0.02188 -0.03456 AFIX 43 H14 5 0.848302 0.915280 0.714696 11.00000 -1.20000 AFIX 0 HKLF 4 REM JBB_0ma_a.res in P2(1)/c REM wR2 = 0.1182, GooF = S = 1.037, Restrained GooF = 1.037 for all data REM R1 = 0.0407 for 2595 Fo > 4sig(Fo) and 0.0601 for all 3414 data REM 253 parameters refined using 0 restraints END WGHT 0.0374 0.6709 REM Highest difference peak 0.183, deepest hole -0.199, 1-sigma level 0.030 Q1 1 0.9576 0.8131 0.7490 11.00000 0.05 0.18 Q2 1 0.2768 0.3667 0.5466 11.00000 0.05 0.13 Q3 1 0.3437 0.4113 0.5970 11.00000 0.05 0.13 Q4 1 0.5813 0.5659 0.7516 11.00000 0.05 0.12 Q5 1 0.3660 0.3236 0.5611 11.00000 0.05 0.12 Q6 1 0.0159 0.3553 0.4419 11.00000 0.05 0.12 Q7 1 0.4939 0.5757 0.6800 11.00000 0.05 0.12 Q8 1 0.5735 0.1720 0.5230 11.00000 0.05 0.11 Q9 1 0.8504 0.7776 0.7705 11.00000 0.05 0.11 Q10 1 0.3726 0.1619 0.5026 11.00000 0.05 0.10 Q11 1 0.6240 0.8988 0.7126 11.00000 0.05 0.10 Q12 1 0.5447 0.2573 0.5586 11.00000 0.05 0.10 Q13 1 0.3391 0.4956 0.6394 11.00000 0.05 0.10 Q14 1 0.1864 0.4023 0.4900 11.00000 0.05 0.10 Q15 1 0.0214 0.3340 0.5001 11.00000 0.05 0.10 Q16 1 0.4626 0.7568 0.6687 11.00000 0.05 0.10 Q17 1 0.7759 0.8328 0.7564 11.00000 0.05 0.09 Q18 1 0.2027 0.3283 0.4962 11.00000 0.05 0.09 Q19 1 0.8622 0.1512 0.6403 11.00000 0.05 0.09 Q20 1 0.2012 0.2694 0.5383 11.00000 0.05 0.09 ; _shelx_res_checksum 97687 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 0.52791(5) 0.66236(8) 0.72338(3) 0.0737(2) Uani 1 1 d . . . . . N1 N 0.54836(13) 0.4446(2) 0.62391(9) 0.0573(4) Uani 1 1 d . . . . . F2 F 0.98688(13) 0.6988(3) 0.76960(9) 0.1364(8) Uani 1 1 d . . . . . C2 C 0.36781(15) 0.4967(2) 0.61979(10) 0.0520(5) Uani 1 1 d . . . . . C3 C 0.32761(15) 0.3921(2) 0.55873(10) 0.0507(4) Uani 1 1 d . . . . . N2 N 0.24640(16) 0.6563(2) 0.67708(12) 0.0794(6) Uani 1 1 d . . . . . C18 C 0.21163(15) 0.3569(2) 0.52500(10) 0.0518(5) Uani 1 1 d . . . . . C5 C 0.51029(15) 0.3409(2) 0.56579(10) 0.0517(5) Uani 1 1 d . . . . . C1 C 0.47904(16) 0.5204(2) 0.64919(11) 0.0553(5) Uani 1 1 d . . . . . C4 C 0.40146(15) 0.3173(2) 0.53177(10) 0.0536(5) Uani 1 1 d . . . . . H4 H 0.377464 0.250148 0.490196 0.064 Uiso 1 1 calc R U . . . C6 C 0.59217(15) 0.2530(2) 0.54293(11) 0.0553(5) Uani 1 1 d . . . . . C19 C 0.15236(16) 0.3056(3) 0.56804(12) 0.0627(5) Uani 1 1 d . . . . . H19 H 0.184456 0.299400 0.618952 0.075 Uiso 1 1 calc R U . . . C12 C 0.66564(17) 0.6701(3) 0.73378(11) 0.0615(5) Uani 1 1 d . . . . . C24 C 0.29861(17) 0.5852(3) 0.65073(11) 0.0595(5) Uani 1 1 d . . . . . C11 C 0.56723(19) 0.1767(3) 0.47456(12) 0.0645(6) Uani 1 1 d . . . . . H11 H 0.497326 0.180587 0.441959 0.077 Uiso 1 1 calc R U . . . C10 C 0.6454(2) 0.0948(3) 0.45435(14) 0.0753(7) Uani 1 1 d . . . . . H10 H 0.627812 0.044887 0.408255 0.090 Uiso 1 1 calc R U . . . C23 C 0.16209(18) 0.3669(3) 0.44953(12) 0.0703(6) Uani 1 1 d . . . . . H23 H 0.200937 0.400455 0.419549 0.084 Uiso 1 1 calc R U . . . C13 C 0.7087(2) 0.8113(3) 0.71470(12) 0.0713(6) Uani 1 1 d . . . . . H13 H 0.664673 0.900444 0.693704 0.086 Uiso 1 1 calc R U . . . C17 C 0.7319(2) 0.5387(3) 0.76429(13) 0.0757(6) Uani 1 1 d . . . . . H17 H 0.702922 0.443550 0.777458 0.091 Uiso 1 1 calc R U . . . C21 C -0.00248(19) 0.2749(3) 0.46200(14) 0.0812(7) Uani 1 1 d . . . . . H21 H -0.074446 0.247261 0.440891 0.097 Uiso 1 1 calc R U . . . C9 C 0.7484(2) 0.0873(3) 0.50210(18) 0.0840(8) Uani 1 1 d . . . . . H9 H 0.800940 0.033153 0.488332 0.101 Uiso 1 1 calc R U . . . C20 C 0.04607(18) 0.2635(3) 0.53639(14) 0.0758(7) Uani 1 1 d . . . . . H20 H 0.007247 0.227129 0.565927 0.091 Uiso 1 1 calc R U . . . C7 C 0.69703(17) 0.2433(3) 0.59051(14) 0.0747(6) Uani 1 1 d . . . . . H7 H 0.715597 0.293589 0.636581 0.090 Uiso 1 1 calc R U . . . C16 C 0.8393(2) 0.5457(4) 0.77555(14) 0.0882(8) Uani 1 1 d . . . . . H16 H 0.883603 0.456049 0.795444 0.106 Uiso 1 1 calc R U . . . C22 C 0.0546(2) 0.3270(3) 0.41850(13) 0.0837(7) Uani 1 1 d . . . . . H22 H 0.021183 0.335755 0.367789 0.100 Uiso 1 1 calc R U . . . C15 C 0.8796(2) 0.6866(5) 0.75697(13) 0.0891(8) Uani 1 1 d . . . . . C8 C 0.7740(2) 0.1599(3) 0.57029(17) 0.0895(8) Uani 1 1 d . . . . . H8 H 0.843686 0.152936 0.603076 0.107 Uiso 1 1 calc R U . . . C14 C 0.8180(2) 0.8203(4) 0.72683(13) 0.0877(8) Uani 1 1 d . . . . . H14 H 0.848302 0.915280 0.714696 0.105 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 0.0685(4) 0.0717(4) 0.0756(4) -0.0257(3) 0.0170(3) -0.0081(3) N1 0.0569(10) 0.0513(10) 0.0631(10) -0.0048(8) 0.0190(8) -0.0061(8) F2 0.0697(10) 0.234(3) 0.1027(12) -0.0177(13) 0.0244(9) -0.0100(12) C2 0.0571(12) 0.0443(10) 0.0557(11) -0.0002(9) 0.0202(9) -0.0037(9) C3 0.0547(11) 0.0442(10) 0.0541(11) 0.0022(8) 0.0191(9) -0.0056(9) N2 0.0818(14) 0.0679(13) 0.0927(14) -0.0193(11) 0.0344(12) 0.0016(10) C18 0.0525(11) 0.0461(11) 0.0563(11) -0.0030(8) 0.0172(9) -0.0031(8) C5 0.0555(11) 0.0428(10) 0.0579(11) 0.0004(9) 0.0203(9) -0.0059(8) C1 0.0602(12) 0.0474(11) 0.0568(11) -0.0040(9) 0.0171(9) -0.0051(9) C4 0.0573(12) 0.0498(11) 0.0551(11) -0.0065(9) 0.0203(9) -0.0097(9) C6 0.0570(12) 0.0433(10) 0.0704(13) 0.0016(9) 0.0276(10) -0.0057(9) C19 0.0564(12) 0.0733(14) 0.0592(12) 0.0005(10) 0.0201(10) -0.0076(10) C12 0.0667(13) 0.0570(12) 0.0511(11) -0.0103(9) 0.0066(9) -0.0079(10) C24 0.0619(13) 0.0497(12) 0.0660(13) -0.0064(10) 0.0199(10) -0.0054(10) C11 0.0742(14) 0.0527(12) 0.0740(14) 0.0011(10) 0.0346(11) -0.0026(10) C10 0.0956(19) 0.0547(13) 0.0926(17) -0.0048(12) 0.0541(15) -0.0044(13) C23 0.0702(14) 0.0822(16) 0.0583(12) -0.0018(11) 0.0210(11) -0.0127(12) C13 0.0803(16) 0.0652(14) 0.0570(12) -0.0001(10) 0.0073(11) -0.0079(12) C17 0.0788(17) 0.0649(15) 0.0732(15) -0.0016(12) 0.0116(12) -0.0003(12) C21 0.0520(13) 0.0963(19) 0.0875(17) -0.0085(15) 0.0124(12) -0.0091(12) C9 0.0828(18) 0.0615(15) 0.130(2) 0.0031(15) 0.0649(18) 0.0040(13) C20 0.0571(13) 0.0940(18) 0.0788(16) -0.0017(13) 0.0259(12) -0.0117(12) C7 0.0579(13) 0.0791(16) 0.0897(16) -0.0095(13) 0.0279(12) -0.0060(12) C16 0.0835(19) 0.097(2) 0.0711(16) -0.0040(15) 0.0082(13) 0.0178(16) C22 0.0726(16) 0.104(2) 0.0618(14) -0.0042(13) 0.0050(12) -0.0100(14) C15 0.0623(16) 0.140(3) 0.0575(14) -0.0114(16) 0.0101(12) 0.0014(17) C8 0.0614(15) 0.0918(19) 0.120(2) -0.0028(17) 0.0355(15) 0.0014(13) C14 0.0856(19) 0.111(2) 0.0647(15) -0.0031(15) 0.0219(13) -0.0346(17) 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' 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' H H 0.0000 0.0000 '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 C12 S1 C1 101.63(9) . . ? C1 N1 C5 118.43(17) . . ? C3 C2 C1 118.46(17) . . ? C3 C2 C24 122.00(17) . . ? C1 C2 C24 119.48(17) . . ? C4 C3 C2 117.18(17) . . ? C4 C3 C18 120.56(17) . . ? C2 C3 C18 122.24(17) . . ? C19 C18 C23 118.75(18) . . ? C19 C18 C3 120.48(17) . . ? C23 C18 C3 120.69(18) . . ? N1 C5 C4 121.38(17) . . ? N1 C5 C6 115.69(17) . . ? C4 C5 C6 122.91(17) . . ? N1 C1 C2 123.45(18) . . ? N1 C1 S1 118.78(15) . . ? C2 C1 S1 117.76(15) . . ? C5 C4 C3 120.99(18) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C7 C6 C11 118.1(2) . . ? C7 C6 C5 120.13(19) . . ? C11 C6 C5 121.75(19) . . ? C20 C19 C18 120.6(2) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C13 C12 C17 119.3(2) . . ? C13 C12 S1 120.09(18) . . ? C17 C12 S1 120.49(18) . . ? N2 C24 C2 177.9(2) . . ? C10 C11 C6 120.7(2) . . ? C10 C11 H11 119.6 . . ? C6 C11 H11 119.6 . . ? C9 C10 C11 120.2(2) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C18 C23 C22 120.0(2) . . ? C18 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C12 C13 C14 119.9(2) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C16 C17 C12 121.1(2) . . ? C16 C17 H17 119.4 . . ? C12 C17 H17 119.4 . . ? C20 C21 C22 119.9(2) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C10 C9 C8 119.8(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C21 C20 C19 120.3(2) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C8 C7 C6 120.8(2) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C15 C16 C17 118.2(3) . . ? C15 C16 H16 120.9 . . ? C17 C16 H16 120.9 . . ? C21 C22 C23 120.3(2) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C16 C15 F2 119.5(3) . . ? C16 C15 C14 123.1(3) . . ? F2 C15 C14 117.4(3) . . ? C9 C8 C7 120.4(3) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C15 C14 C13 118.3(3) . . ? C15 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? 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 C12 1.767(2) . ? S1 C1 1.776(2) . ? N1 C1 1.321(2) . ? N1 C5 1.352(2) . ? F2 C15 1.361(3) . ? C2 C3 1.400(3) . ? C2 C1 1.404(3) . ? C2 C24 1.436(3) . ? C3 C4 1.386(3) . ? C3 C18 1.482(3) . ? N2 C24 1.138(3) . ? C18 C19 1.378(3) . ? C18 C23 1.382(3) . ? C5 C4 1.383(3) . ? C5 C6 1.478(3) . ? C4 H4 0.9300 . ? C6 C7 1.388(3) . ? C6 C11 1.388(3) . ? C19 C20 1.377(3) . ? C19 H19 0.9300 . ? C12 C13 1.377(3) . ? C12 C17 1.377(3) . ? C11 C10 1.387(3) . ? C11 H11 0.9300 . ? C10 C9 1.370(4) . ? C10 H10 0.9300 . ? C23 C22 1.385(3) . ? C23 H23 0.9300 . ? C13 C14 1.387(3) . ? C13 H13 0.9300 . ? C17 C16 1.366(3) . ? C17 H17 0.9300 . ? C21 C20 1.363(3) . ? C21 C22 1.365(3) . ? C21 H21 0.9300 . ? C9 C8 1.372(4) . ? C9 H9 0.9300 . ? C20 H20 0.9300 . ? C7 C8 1.379(3) . ? C7 H7 0.9300 . ? C16 C15 1.353(4) . ? C16 H16 0.9300 . ? C22 H22 0.9300 . ? C15 C14 1.362(4) . ? C8 H8 0.9300 . ? C14 H14 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 C1 C2 C3 C4 0.6(3) . . . . ? C24 C2 C3 C4 177.77(17) . . . . ? C1 C2 C3 C18 178.67(17) . . . . ? C24 C2 C3 C18 -4.1(3) . . . . ? C4 C3 C18 C19 127.0(2) . . . . ? C2 C3 C18 C19 -51.0(3) . . . . ? C4 C3 C18 C23 -49.8(3) . . . . ? C2 C3 C18 C23 132.2(2) . . . . ? C1 N1 C5 C4 1.8(3) . . . . ? C1 N1 C5 C6 -176.68(17) . . . . ? C5 N1 C1 C2 1.3(3) . . . . ? C5 N1 C1 S1 -177.76(14) . . . . ? C3 C2 C1 N1 -2.5(3) . . . . ? C24 C2 C1 N1 -179.72(18) . . . . ? C3 C2 C1 S1 176.58(14) . . . . ? C24 C2 C1 S1 -0.7(2) . . . . ? C12 S1 C1 N1 5.89(18) . . . . ? C12 S1 C1 C2 -173.20(16) . . . . ? N1 C5 C4 C3 -3.6(3) . . . . ? C6 C5 C4 C3 174.72(17) . . . . ? C2 C3 C4 C5 2.3(3) . . . . ? C18 C3 C4 C5 -175.82(17) . . . . ? N1 C5 C6 C7 17.2(3) . . . . ? C4 C5 C6 C7 -161.2(2) . . . . ? N1 C5 C6 C11 -163.54(18) . . . . ? C4 C5 C6 C11 18.0(3) . . . . ? C23 C18 C19 C20 0.7(3) . . . . ? C3 C18 C19 C20 -176.2(2) . . . . ? C1 S1 C12 C13 110.18(18) . . . . ? C1 S1 C12 C17 -73.00(19) . . . . ? C7 C6 C11 C10 -0.7(3) . . . . ? C5 C6 C11 C10 -179.96(18) . . . . ? C6 C11 C10 C9 0.5(3) . . . . ? C19 C18 C23 C22 0.5(3) . . . . ? C3 C18 C23 C22 177.3(2) . . . . ? C17 C12 C13 C14 -0.5(3) . . . . ? S1 C12 C13 C14 176.36(17) . . . . ? C13 C12 C17 C16 -0.4(3) . . . . ? S1 C12 C17 C16 -177.21(18) . . . . ? C11 C10 C9 C8 0.5(4) . . . . ? C22 C21 C20 C19 0.5(4) . . . . ? C18 C19 C20 C21 -1.2(4) . . . . ? C11 C6 C7 C8 -0.1(3) . . . . ? C5 C6 C7 C8 179.2(2) . . . . ? C12 C17 C16 C15 1.0(4) . . . . ? C20 C21 C22 C23 0.6(4) . . . . ? C18 C23 C22 C21 -1.1(4) . . . . ? C17 C16 C15 F2 178.1(2) . . . . ? C17 C16 C15 C14 -0.9(4) . . . . ? C10 C9 C8 C7 -1.3(4) . . . . ? C6 C7 C8 C9 1.1(4) . . . . ? C16 C15 C14 C13 0.0(4) . . . . ? F2 C15 C14 C13 -178.9(2) . . . . ? C12 C13 C14 C15 0.7(3) . . . . ?