#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:22:26 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288818 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247728.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_7247728 loop_ _publ_author_name 'Pan, Dongping' 'Liu, Fu-Xiaomin' 'Zeng, Zhongyi' 'Ye, Junwei' 'Cai, Ying' 'Wang, Shengdong' 'Zhou, Zhi' 'Yi, Wei' _publ_section_title ; Practical conversion of gem-difluorocyclopropenes for the chemodivergent assembly of fluorinated heterocyclic frameworks ; _journal_issue 24 _journal_name_full 'Green Chemistry' _journal_page_first 10630 _journal_page_last 10637 _journal_paper_doi 10.1039/D3GC03203E _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C24 H21 F N2 O3 S' _chemical_formula_sum 'C24 H21 F N2 O3 S' _chemical_formula_weight 436.49 _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 _atom_sites_solution_primary dual _audit_creation_date 2023-04-27 _audit_creation_method ; Olex2 1.5-beta (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439) ; _audit_update_record ; 2023-07-07 deposited with the CCDC. 2023-11-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 117.375(15) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.0253(12) _cell_length_b 19.0234(19) _cell_length_c 11.0800(13) _cell_measurement_reflns_used 5453 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 29.2470 _cell_measurement_theta_min 2.3110 _cell_volume 2063.7(5) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -37.00 65.00 1.00 5.00 -- -11.27 77.00 0.00 102 2 \w 30.00 57.00 1.00 5.00 -- -11.27 77.00-120.00 27 3 \w -15.00 88.00 1.00 5.00 -- 11.90 77.00 -90.00 103 4 \w -20.00 5.00 1.00 5.00 -- 11.90 77.00 150.00 25 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0356248000 _diffrn_orient_matrix_UB_12 0.0107812000 _diffrn_orient_matrix_UB_13 -0.0688920000 _diffrn_orient_matrix_UB_21 0.0130173000 _diffrn_orient_matrix_UB_22 -0.0331612000 _diffrn_orient_matrix_UB_23 -0.0209462000 _diffrn_orient_matrix_UB_31 -0.0616940000 _diffrn_orient_matrix_UB_32 -0.0132166000 _diffrn_orient_matrix_UB_33 -0.0035454000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_unetI/netI 0.0427 _diffrn_reflns_Laue_measured_fraction_full 0.982 _diffrn_reflns_Laue_measured_fraction_max 0.982 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 11871 _diffrn_reflns_point_group_measured_fraction_full 0.982 _diffrn_reflns_point_group_measured_fraction_max 0.982 _diffrn_reflns_theta_full 24.997 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 2.080 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.196 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.22970 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'light colourless' _exptl_crystal_density_diffrn 1.405 _exptl_crystal_description block _exptl_crystal_F_000 912 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.310 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.058 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 282 _refine_ls_number_reflns 3564 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.073 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0422 _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^)+(0.0433P)^2^+1.1412P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0986 _refine_ls_wR_factor_ref 0.1036 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3111 _reflns_number_total 3564 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03203e2.cif _cod_data_source_block 429 _cod_depositor_comments 'Adding full bibliography for 7247725--7247728.cif.' _cod_database_code 7247728 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C16(H16A,H16B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C19(H19), C20(H20), C22(H22), C23(H23) 2.c Idealised Me refined as rotating group: C17(H17A,H17B,H17C), C24(H24A,H24B,H24C) ; _shelx_res_file ; TITL 429_a.res in P2(1)/c 429.res created by SHELXL-2018/3 at 20:20:09 on 27-Apr-2023 REM Old TITL 429 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.203, Rweak 0.160, Alpha 0.037 REM 0.822 for 95 systematic absences, Orientation as input REM Formula found by SHELXT: C24 N2 O3 S F CELL 0.71073 11.025347 19.023354 11.079989 90 117.3754 90 ZERR 4 0.001211 0.001894 0.001263 0 0.0146 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N O S UNIT 96 84 4 8 12 4 L.S. 10 PLAN 5 TEMP -120 CONF BOND list 4 fmap 2 acta MORE -1 BOND $H OMIT -3 50 REM REM REM WGHT 0.043300 1.141200 FVAR 5.23108 S1 6 0.922471 0.422264 0.785393 11.00000 0.01676 0.02385 = 0.01848 0.00266 0.00857 0.00175 F1 3 0.522795 0.435142 0.600035 11.00000 0.02353 0.03229 = 0.01686 0.00793 0.00581 -0.00117 O1 5 0.861835 0.570852 0.802040 11.00000 0.02850 0.02418 = 0.03026 -0.00151 0.01671 -0.00767 O2 5 0.915689 0.348822 0.807371 11.00000 0.03020 0.02315 = 0.02768 0.00637 0.01583 0.00607 O3 5 1.047517 0.459125 0.857650 11.00000 0.01629 0.03931 = 0.02464 0.00217 0.00797 -0.00134 N1 4 0.715584 0.372098 0.930012 11.00000 0.01537 0.01771 = 0.01502 -0.00049 0.00573 -0.00036 N2 4 0.805408 0.458228 0.828146 11.00000 0.01650 0.01869 = 0.02005 -0.00063 0.01019 -0.00200 C1 1 0.357934 0.331439 0.679858 11.00000 0.01704 0.01312 = 0.01862 -0.00044 0.00597 0.00022 C2 1 0.302000 0.324793 0.538872 11.00000 0.02040 0.02462 = 0.02276 -0.00359 0.01048 0.00222 AFIX 43 H2 2 0.357500 0.333353 0.495489 11.00000 -1.20000 AFIX 0 C3 1 0.166594 0.305872 0.461671 11.00000 0.02280 0.03046 = 0.02037 -0.00642 0.00395 -0.00011 AFIX 43 H3 2 0.129806 0.301628 0.365835 11.00000 -1.20000 AFIX 0 C4 1 0.084607 0.293115 0.523406 11.00000 0.01725 0.02780 = 0.03323 -0.00093 0.00423 -0.00307 AFIX 43 H4 2 -0.007949 0.279463 0.470424 11.00000 -1.20000 AFIX 0 C5 1 0.138099 0.300343 0.662546 11.00000 0.02074 0.02454 = 0.03409 0.00585 0.01355 0.00035 AFIX 43 H5 2 0.081792 0.292162 0.705183 11.00000 -1.20000 AFIX 0 C6 1 0.273770 0.319506 0.740429 11.00000 0.02161 0.01999 = 0.02035 0.00296 0.00900 0.00095 AFIX 43 H6 2 0.309482 0.324520 0.836025 11.00000 -1.20000 AFIX 0 C7 1 0.501026 0.354170 0.759520 11.00000 0.01620 0.01675 = 0.01722 -0.00197 0.00782 -0.00017 C8 1 0.572885 0.401218 0.720124 11.00000 0.01970 0.01786 = 0.01377 0.00277 0.00746 0.00359 C9 1 0.702102 0.413216 0.821735 11.00000 0.01792 0.01789 = 0.01664 -0.00035 0.00883 -0.00009 C10 1 0.593015 0.335606 0.893226 11.00000 0.01647 0.01634 = 0.01875 -0.00179 0.00901 -0.00025 C11 1 0.587791 0.289575 0.990878 11.00000 0.02250 0.01685 = 0.02299 0.00045 0.01089 0.00045 AFIX 43 H11 2 0.507071 0.263374 0.969448 11.00000 -1.20000 AFIX 0 C12 1 0.697444 0.282574 1.115135 11.00000 0.02906 0.02340 = 0.02300 0.00516 0.01482 0.00436 AFIX 43 H12 2 0.692782 0.251999 1.180668 11.00000 -1.20000 AFIX 0 C13 1 0.818561 0.320716 1.147155 11.00000 0.01983 0.03246 = 0.01692 0.00371 0.00387 0.00592 AFIX 43 H13 2 0.894706 0.315666 1.234426 11.00000 -1.20000 AFIX 0 C14 1 0.827269 0.364231 1.055157 11.00000 0.01523 0.02826 = 0.01835 -0.00136 0.00430 0.00028 AFIX 43 H14 2 0.909435 0.389072 1.076598 11.00000 -1.20000 AFIX 0 C15 1 0.789091 0.532536 0.826047 11.00000 0.01968 0.02225 = 0.01486 -0.00167 0.00649 -0.00239 C16 1 0.674670 0.557790 0.853299 11.00000 0.02274 0.02374 = 0.02198 -0.00100 0.01074 -0.00020 AFIX 23 H16A 2 0.679613 0.533249 0.934232 11.00000 -1.20000 H16B 2 0.586148 0.545760 0.774870 11.00000 -1.20000 AFIX 0 C17 1 0.681044 0.636297 0.877059 11.00000 0.03728 0.02835 = 0.05143 -0.00775 0.02581 -0.00043 AFIX 137 H17A 2 0.675643 0.660798 0.796931 11.00000 -1.50000 H17B 2 0.767256 0.648232 0.956503 11.00000 -1.50000 H17C 2 0.604362 0.650729 0.893139 11.00000 -1.50000 AFIX 0 C18 1 0.853622 0.438331 0.610388 11.00000 0.01836 0.02324 = 0.01882 0.00139 0.01055 0.00199 C19 1 0.880999 0.500820 0.564065 11.00000 0.01998 0.02206 = 0.02346 -0.00044 0.01186 -0.00044 AFIX 43 H19 2 0.940757 0.534502 0.626320 11.00000 -1.20000 AFIX 0 C20 1 0.820237 0.513558 0.426037 11.00000 0.02415 0.02271 = 0.02711 0.00554 0.01611 0.00439 AFIX 43 H20 2 0.839137 0.556283 0.393559 11.00000 -1.20000 AFIX 0 C21 1 0.731825 0.464992 0.333582 11.00000 0.02000 0.02714 = 0.02253 0.00145 0.01223 0.00594 C22 1 0.707007 0.402327 0.382756 11.00000 0.02785 0.02946 = 0.02239 -0.00468 0.01156 -0.00408 AFIX 43 H22 2 0.647593 0.368514 0.320573 11.00000 -1.20000 AFIX 0 C23 1 0.767124 0.388315 0.520330 11.00000 0.02953 0.02115 = 0.02594 0.00028 0.01482 -0.00251 AFIX 43 H23 2 0.749734 0.345250 0.552972 11.00000 -1.20000 AFIX 0 C24 1 0.666221 0.481170 0.183874 11.00000 0.02877 0.03587 = 0.02260 0.00268 0.01329 0.00484 AFIX 137 H24A 2 0.615764 0.439852 0.132454 11.00000 -1.50000 H24B 2 0.737022 0.493380 0.157368 11.00000 -1.50000 H24C 2 0.603166 0.520810 0.164338 11.00000 -1.50000 AFIX 0 HKLF 4 REM 429_a.res in P2(1)/c REM wR2 = 0.1036, GooF = S = 1.073, Restrained GooF = 1.073 for all data REM R1 = 0.0422 for 3111 Fo > 4sig(Fo) and 0.0518 for all 3564 data REM 282 parameters refined using 0 restraints END WGHT 0.0426 1.1042 REM Highest difference peak 0.310, deepest hole -0.436, 1-sigma level 0.058 Q1 1 0.8808 0.4340 0.6819 11.00000 0.05 0.31 Q2 1 0.7400 0.4975 0.3859 11.00000 0.05 0.26 Q3 1 0.7840 0.3843 0.4373 11.00000 0.05 0.23 Q4 1 0.7417 0.6664 0.8647 11.00000 0.05 0.22 Q5 1 0.6409 0.3513 0.9037 11.00000 0.05 0.22 ; _shelx_res_checksum 17546 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 2.334 _oxdiff_exptl_absorpt_empirical_full_min 0.445 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 0.92247(5) 0.42226(3) 0.78539(5) 0.01952(15) Uani 1 1 d . . . . . F1 F 0.52280(11) 0.43514(6) 0.60004(11) 0.0256(3) Uani 1 1 d . . . . . O1 O 0.86184(14) 0.57085(7) 0.80204(15) 0.0264(4) Uani 1 1 d . . . . . O2 O 0.91569(14) 0.34882(7) 0.80737(14) 0.0260(4) Uani 1 1 d . . . . . O3 O 1.04752(13) 0.45913(8) 0.85765(14) 0.0273(4) Uani 1 1 d . . . . . N1 N 0.71558(15) 0.37210(8) 0.93001(15) 0.0165(4) Uani 1 1 d . . . . . N2 N 0.80541(15) 0.45823(8) 0.82815(16) 0.0177(4) Uani 1 1 d . . . . . C1 C 0.35793(19) 0.33144(9) 0.67986(19) 0.0171(4) Uani 1 1 d . . . . . C2 C 0.3020(2) 0.32479(10) 0.5389(2) 0.0224(5) Uani 1 1 d . . . . . H2 H 0.357500 0.333353 0.495489 0.027 Uiso 1 1 calc R U . . . C3 C 0.1666(2) 0.30587(11) 0.4617(2) 0.0269(5) Uani 1 1 d . . . . . H3 H 0.129806 0.301628 0.365835 0.032 Uiso 1 1 calc R U . . . C4 C 0.0846(2) 0.29312(11) 0.5234(2) 0.0290(5) Uani 1 1 d . . . . . H4 H -0.007949 0.279463 0.470424 0.035 Uiso 1 1 calc R U . . . C5 C 0.1381(2) 0.30034(11) 0.6625(2) 0.0261(5) Uani 1 1 d . . . . . H5 H 0.081792 0.292162 0.705183 0.031 Uiso 1 1 calc R U . . . C6 C 0.2738(2) 0.31951(10) 0.7404(2) 0.0209(5) Uani 1 1 d . . . . . H6 H 0.309482 0.324520 0.836025 0.025 Uiso 1 1 calc R U . . . C7 C 0.50103(19) 0.35417(10) 0.75952(19) 0.0167(4) Uani 1 1 d . . . . . C8 C 0.57289(19) 0.40122(10) 0.72012(19) 0.0172(4) Uani 1 1 d . . . . . C9 C 0.70210(19) 0.41322(10) 0.82173(19) 0.0171(4) Uani 1 1 d . . . . . C10 C 0.59301(19) 0.33561(10) 0.89323(19) 0.0168(4) Uani 1 1 d . . . . . C11 C 0.5878(2) 0.28957(10) 0.9909(2) 0.0206(5) Uani 1 1 d . . . . . H11 H 0.507071 0.263374 0.969448 0.025 Uiso 1 1 calc R U . . . C12 C 0.6974(2) 0.28257(11) 1.1151(2) 0.0240(5) Uani 1 1 d . . . . . H12 H 0.692782 0.251999 1.180668 0.029 Uiso 1 1 calc R U . . . C13 C 0.8186(2) 0.32072(11) 1.1472(2) 0.0249(5) Uani 1 1 d . . . . . H13 H 0.894706 0.315666 1.234426 0.030 Uiso 1 1 calc R U . . . C14 C 0.8273(2) 0.36423(11) 1.0552(2) 0.0219(5) Uani 1 1 d . . . . . H14 H 0.909435 0.389072 1.076598 0.026 Uiso 1 1 calc R U . . . C15 C 0.78909(19) 0.53254(10) 0.82605(19) 0.0195(4) Uani 1 1 d . . . . . C16 C 0.6747(2) 0.55779(11) 0.8533(2) 0.0226(5) Uani 1 1 d . . . . . H16A H 0.679613 0.533249 0.934232 0.027 Uiso 1 1 calc R U . . . H16B H 0.586148 0.545760 0.774870 0.027 Uiso 1 1 calc R U . . . C17 C 0.6810(2) 0.63630(12) 0.8771(3) 0.0369(6) Uani 1 1 d . . . . . H17A H 0.675643 0.660798 0.796931 0.055 Uiso 1 1 calc R U . . . H17B H 0.767256 0.648232 0.956503 0.055 Uiso 1 1 calc R U . . . H17C H 0.604362 0.650729 0.893139 0.055 Uiso 1 1 calc R U . . . C18 C 0.85362(19) 0.43833(10) 0.6104(2) 0.0194(4) Uani 1 1 d . . . . . C19 C 0.8810(2) 0.50082(11) 0.5641(2) 0.0211(5) Uani 1 1 d . . . . . H19 H 0.940757 0.534502 0.626320 0.025 Uiso 1 1 calc R U . . . C20 C 0.8202(2) 0.51356(11) 0.4260(2) 0.0230(5) Uani 1 1 d . . . . . H20 H 0.839137 0.556283 0.393559 0.028 Uiso 1 1 calc R U . . . C21 C 0.7318(2) 0.46499(11) 0.3336(2) 0.0223(5) Uani 1 1 d . . . . . C22 C 0.7070(2) 0.40233(11) 0.3828(2) 0.0266(5) Uani 1 1 d . . . . . H22 H 0.647593 0.368514 0.320573 0.032 Uiso 1 1 calc R U . . . C23 C 0.7671(2) 0.38832(11) 0.5203(2) 0.0247(5) Uani 1 1 d . . . . . H23 H 0.749734 0.345250 0.552972 0.030 Uiso 1 1 calc R U . . . C24 C 0.6662(2) 0.48117(12) 0.1839(2) 0.0285(5) Uani 1 1 d . . . . . H24A H 0.615764 0.439852 0.132454 0.043 Uiso 1 1 calc R U . . . H24B H 0.737022 0.493380 0.157368 0.043 Uiso 1 1 calc R U . . . H24C H 0.603166 0.520810 0.164338 0.043 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 0.0168(3) 0.0238(3) 0.0185(3) 0.00266(19) 0.0086(2) 0.00175(19) F1 0.0235(6) 0.0323(7) 0.0169(6) 0.0079(5) 0.0058(5) -0.0012(5) O1 0.0285(8) 0.0242(8) 0.0303(8) -0.0015(6) 0.0167(7) -0.0077(6) O2 0.0302(8) 0.0231(8) 0.0277(8) 0.0064(6) 0.0158(7) 0.0061(6) O3 0.0163(7) 0.0393(9) 0.0246(8) 0.0022(6) 0.0080(6) -0.0013(6) N1 0.0154(8) 0.0177(9) 0.0150(8) -0.0005(6) 0.0057(7) -0.0004(6) N2 0.0165(8) 0.0187(9) 0.0200(9) -0.0006(7) 0.0102(7) -0.0020(6) C1 0.0170(9) 0.0131(10) 0.0186(10) -0.0004(7) 0.0060(8) 0.0002(7) C2 0.0204(10) 0.0246(11) 0.0228(11) -0.0036(8) 0.0105(9) 0.0022(8) C3 0.0228(11) 0.0305(12) 0.0204(11) -0.0064(9) 0.0040(9) -0.0001(9) C4 0.0172(10) 0.0278(12) 0.0332(13) -0.0009(9) 0.0042(10) -0.0031(9) C5 0.0207(11) 0.0245(12) 0.0341(13) 0.0059(9) 0.0135(10) 0.0003(8) C6 0.0216(10) 0.0200(11) 0.0203(11) 0.0030(8) 0.0090(9) 0.0010(8) C7 0.0162(9) 0.0168(10) 0.0172(10) -0.0020(7) 0.0078(8) -0.0002(8) C8 0.0197(10) 0.0179(10) 0.0138(10) 0.0028(7) 0.0075(8) 0.0036(8) C9 0.0179(10) 0.0179(10) 0.0166(10) -0.0004(8) 0.0088(8) -0.0001(8) C10 0.0165(9) 0.0163(10) 0.0188(10) -0.0018(8) 0.0090(8) -0.0003(7) C11 0.0225(10) 0.0169(11) 0.0230(11) 0.0004(8) 0.0109(9) 0.0004(8) C12 0.0291(11) 0.0234(11) 0.0230(11) 0.0052(8) 0.0148(10) 0.0044(9) C13 0.0198(10) 0.0325(12) 0.0169(10) 0.0037(9) 0.0039(9) 0.0059(9) C14 0.0152(10) 0.0283(12) 0.0184(10) -0.0014(8) 0.0043(9) 0.0003(8) C15 0.0197(10) 0.0222(11) 0.0149(10) -0.0017(8) 0.0065(9) -0.0024(8) C16 0.0227(10) 0.0237(11) 0.0220(11) -0.0010(8) 0.0107(9) -0.0002(8) C17 0.0373(13) 0.0283(13) 0.0514(16) -0.0077(11) 0.0258(12) -0.0004(10) C18 0.0184(10) 0.0232(11) 0.0188(10) 0.0014(8) 0.0106(9) 0.0020(8) C19 0.0200(10) 0.0221(11) 0.0235(11) -0.0004(8) 0.0119(9) -0.0004(8) C20 0.0242(10) 0.0227(11) 0.0271(11) 0.0055(9) 0.0161(10) 0.0044(8) C21 0.0200(10) 0.0271(12) 0.0225(11) 0.0015(8) 0.0122(9) 0.0059(8) C22 0.0278(11) 0.0295(12) 0.0224(11) -0.0047(9) 0.0116(10) -0.0041(9) C23 0.0295(11) 0.0212(11) 0.0259(11) 0.0003(8) 0.0148(10) -0.0025(9) C24 0.0288(11) 0.0359(13) 0.0226(11) 0.0027(9) 0.0133(10) 0.0048(10) 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' 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' 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 O2 S1 N2 103.85(9) . . ? O2 S1 C18 109.24(9) . . ? O3 S1 O2 120.06(9) . . ? O3 S1 N2 107.88(9) . . ? O3 S1 C18 110.58(9) . . ? N2 S1 C18 103.80(9) . . ? C9 N1 C10 108.86(15) . . ? C14 N1 C9 128.76(17) . . ? C14 N1 C10 122.37(17) . . ? C9 N2 S1 116.20(13) . . ? C9 N2 C15 120.83(16) . . ? C15 N2 S1 119.92(14) . . ? C2 C1 C7 119.78(19) . . ? C6 C1 C2 118.38(18) . . ? C6 C1 C7 121.76(17) . . ? C1 C2 H2 119.6 . . ? C3 C2 C1 120.7(2) . . ? C3 C2 H2 119.6 . . ? C2 C3 H3 119.8 . . ? C4 C3 C2 120.3(2) . . ? C4 C3 H3 119.8 . . ? C3 C4 H4 120.2 . . ? C5 C4 C3 119.60(19) . . ? C5 C4 H4 120.2 . . ? C4 C5 H5 119.8 . . ? C4 C5 C6 120.3(2) . . ? C6 C5 H5 119.8 . . ? C1 C6 H6 119.7 . . ? C5 C6 C1 120.66(19) . . ? C5 C6 H6 119.7 . . ? C8 C7 C1 127.41(17) . . ? C8 C7 C10 104.70(16) . . ? C10 C7 C1 127.85(18) . . ? F1 C8 C7 125.71(16) . . ? F1 C8 C9 122.08(18) . . ? C9 C8 C7 112.11(17) . . ? N1 C9 N2 122.81(16) . . ? C8 C9 N1 105.99(17) . . ? C8 C9 N2 131.16(18) . . ? N1 C10 C11 117.20(16) . . ? C7 C10 N1 108.33(17) . . ? C7 C10 C11 134.46(18) . . ? C10 C11 H11 119.8 . . ? C12 C11 C10 120.41(19) . . ? C12 C11 H11 119.8 . . ? C11 C12 H12 119.9 . . ? C11 C12 C13 120.1(2) . . ? C13 C12 H12 119.9 . . ? C12 C13 H13 119.6 . . ? C14 C13 C12 120.79(18) . . ? C14 C13 H13 119.6 . . ? N1 C14 H14 120.4 . . ? C13 C14 N1 119.10(18) . . ? C13 C14 H14 120.4 . . ? O1 C15 N2 120.94(19) . . ? O1 C15 C16 123.90(19) . . ? N2 C15 C16 115.15(17) . . ? C15 C16 H16A 109.2 . . ? C15 C16 H16B 109.2 . . ? C15 C16 C17 111.97(18) . . ? H16A C16 H16B 107.9 . . ? C17 C16 H16A 109.2 . . ? C17 C16 H16B 109.2 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 S1 120.20(15) . . ? C19 C18 C23 121.11(19) . . ? C23 C18 S1 118.64(16) . . ? C18 C19 H19 120.5 . . ? C20 C19 C18 119.01(19) . . ? C20 C19 H19 120.5 . . ? C19 C20 H20 119.4 . . ? C19 C20 C21 121.2(2) . . ? C21 C20 H20 119.4 . . ? C20 C21 C24 119.65(19) . . ? C22 C21 C20 118.61(19) . . ? C22 C21 C24 121.74(19) . . ? C21 C22 H22 119.4 . . ? C23 C22 C21 121.18(19) . . ? C23 C22 H22 119.4 . . ? C18 C23 H23 120.6 . . ? C22 C23 C18 118.9(2) . . ? C22 C23 H23 120.6 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? 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 O2 1.4260(15) . ? S1 O3 1.4207(15) . ? S1 N2 1.7089(17) . ? S1 C18 1.754(2) . ? F1 C8 1.348(2) . ? O1 C15 1.201(2) . ? N1 C9 1.382(2) . ? N1 C10 1.403(2) . ? N1 C14 1.375(2) . ? N2 C9 1.400(2) . ? N2 C15 1.424(3) . ? C1 C2 1.397(3) . ? C1 C6 1.391(3) . ? C1 C7 1.475(3) . ? C2 H2 0.9500 . ? C2 C3 1.384(3) . ? C3 H3 0.9500 . ? C3 C4 1.383(3) . ? C4 H4 0.9500 . ? C4 C5 1.381(3) . ? C5 H5 0.9500 . ? C5 C6 1.389(3) . ? C6 H6 0.9500 . ? C7 C8 1.392(3) . ? C7 C10 1.402(3) . ? C8 C9 1.369(3) . ? C10 C11 1.414(3) . ? C11 H11 0.9500 . ? C11 C12 1.358(3) . ? C12 H12 0.9500 . ? C12 C13 1.414(3) . ? C13 H13 0.9500 . ? C13 C14 1.350(3) . ? C14 H14 0.9500 . ? C15 C16 1.505(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C16 C17 1.513(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.382(3) . ? C18 C23 1.391(3) . ? C19 H19 0.9500 . ? C19 C20 1.380(3) . ? C20 H20 0.9500 . ? C20 C21 1.391(3) . ? C21 C22 1.389(3) . ? C21 C24 1.505(3) . ? C22 H22 0.9500 . ? C22 C23 1.380(3) . ? C23 H23 0.9500 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 N2 C9 N1 88.6(2) . . . . ? S1 N2 C9 C8 -94.1(2) . . . . ? S1 N2 C15 O1 -4.2(2) . . . . ? S1 N2 C15 C16 174.75(13) . . . . ? S1 C18 C19 C20 -176.89(15) . . . . ? S1 C18 C23 C22 176.64(16) . . . . ? F1 C8 C9 N1 177.43(16) . . . . ? F1 C8 C9 N2 -0.3(3) . . . . ? O1 C15 C16 C17 -12.4(3) . . . . ? O2 S1 N2 C9 -23.11(15) . . . . ? O2 S1 N2 C15 176.48(14) . . . . ? O2 S1 C18 C19 -162.42(16) . . . . ? O2 S1 C18 C23 20.14(19) . . . . ? O3 S1 N2 C9 -151.54(14) . . . . ? O3 S1 N2 C15 48.05(16) . . . . ? O3 S1 C18 C19 -28.18(19) . . . . ? O3 S1 C18 C23 154.38(16) . . . . ? N1 C10 C11 C12 0.9(3) . . . . ? N2 S1 C18 C19 87.29(17) . . . . ? N2 S1 C18 C23 -90.15(17) . . . . ? N2 C15 C16 C17 168.66(18) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C1 C7 C8 F1 0.4(3) . . . . ? C1 C7 C8 C9 176.89(19) . . . . ? C1 C7 C10 N1 -177.19(18) . . . . ? C1 C7 C10 C11 4.0(4) . . . . ? C2 C1 C6 C5 1.0(3) . . . . ? C2 C1 C7 C8 33.9(3) . . . . ? C2 C1 C7 C10 -148.9(2) . . . . ? C2 C3 C4 C5 0.9(3) . . . . ? C3 C4 C5 C6 -0.7(3) . . . . ? C4 C5 C6 C1 -0.3(3) . . . . ? C6 C1 C2 C3 -0.9(3) . . . . ? C6 C1 C7 C8 -142.9(2) . . . . ? C6 C1 C7 C10 34.3(3) . . . . ? C7 C1 C2 C3 -177.77(18) . . . . ? C7 C1 C6 C5 177.89(18) . . . . ? C7 C8 C9 N1 0.8(2) . . . . ? C7 C8 C9 N2 -176.9(2) . . . . ? C7 C10 C11 C12 179.6(2) . . . . ? C8 C7 C10 N1 0.5(2) . . . . ? C8 C7 C10 C11 -178.3(2) . . . . ? C9 N1 C10 C7 0.0(2) . . . . ? C9 N1 C10 C11 179.01(17) . . . . ? C9 N1 C14 C13 -179.82(19) . . . . ? C9 N2 C15 O1 -163.75(18) . . . . ? C9 N2 C15 C16 15.3(3) . . . . ? C10 N1 C9 N2 177.48(17) . . . . ? C10 N1 C9 C8 -0.5(2) . . . . ? C10 N1 C14 C13 -1.1(3) . . . . ? C10 C7 C8 F1 -177.29(18) . . . . ? C10 C7 C8 C9 -0.8(2) . . . . ? C10 C11 C12 C13 -0.8(3) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C12 C13 C14 N1 1.2(3) . . . . ? C14 N1 C9 N2 -3.6(3) . . . . ? C14 N1 C9 C8 178.43(18) . . . . ? C14 N1 C10 C7 -178.98(17) . . . . ? C14 N1 C10 C11 0.0(3) . . . . ? C15 N2 C9 N1 -111.2(2) . . . . ? C15 N2 C9 C8 66.2(3) . . . . ? C18 S1 N2 C9 91.10(15) . . . . ? C18 S1 N2 C15 -69.32(16) . . . . ? C18 C19 C20 C21 0.4(3) . . . . ? C19 C18 C23 C22 -0.8(3) . . . . ? C19 C20 C21 C22 -1.0(3) . . . . ? C19 C20 C21 C24 179.27(18) . . . . ? C20 C21 C22 C23 0.7(3) . . . . ? C21 C22 C23 C18 0.2(3) . . . . ? C23 C18 C19 C20 0.5(3) . . . . ? C24 C21 C22 C23 -179.6(2) . . . . ?