#------------------------------------------------------------------------------ #$Date: 2023-11-11 03:01:43 +0200 (Sat, 11 Nov 2023) $ #$Revision: 287534 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247704.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_7247704 loop_ _publ_author_name 'Han, Wei' 'Chen, Yu-Lan' 'Tang, Xi' 'Zhou, Jie' 'Ma, Mengtao' 'Shen, Zhi-Liang' 'Chu, Xue-Qiang' _publ_section_title ; Water-Promoted Defluorinative Synthesis of Fluoroalkylated 1,5-Diazapentadienes by Using (NH4)2CO3 as NH2 and NH Sources ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D3GC03717G _journal_year 2023 _chemical_formula_moiety 'C19 H14 F7 N O3 S' _chemical_formula_sum 'C19 H14 F7 N O3 S' _chemical_formula_weight 469.37 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2023-07-07 _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. 2023-11-08 downloaded from the CCDC. ; _cell_angle_alpha 81.051(7) _cell_angle_beta 85.123(9) _cell_angle_gamma 84.276(11) _cell_formula_units_Z 2 _cell_length_a 6.2755(10) _cell_length_b 8.1410(9) _cell_length_c 19.0094(12) _cell_measurement_reflns_used 3018 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 73.2190 _cell_measurement_theta_min 4.6970 _cell_volume 952.2(2) _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 'SHELXS (Sheldrick, 2008)' _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 0.998 _diffrn_measured_fraction_theta_max 0.998 _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 -63.00 30.00 1.00 1.00 -- -40.73 38.00 30.00 93 2 \w -72.00 23.00 1.00 1.00 -- -40.73 77.00 120.00 95 3 \w 33.00 76.00 1.00 1.00 -- 40.73-125.00 -90.00 43 4 \w 59.00 85.00 1.00 1.00 -- 40.73-125.00 0.00 26 5 \w 52.00 120.00 1.00 1.00 -- 106.95 -45.00 120.00 68 6 \w 83.00 178.00 1.00 1.00 -- 106.95 30.00 60.00 95 7 \w 151.00 177.00 1.00 1.00 -- 106.95 125.00 -30.00 26 8 \w 114.00 155.00 1.00 1.00 -- 106.95 125.00 -90.00 41 9 \w 99.00 130.00 1.00 1.00 -- 106.95 125.00 -30.00 31 10 \w 95.00 165.00 1.00 1.00 -- 106.95 125.00 60.00 70 11 \w 100.00 172.00 1.00 1.00 -- 106.95 30.00 -30.00 72 12 \w 82.00 133.00 1.00 1.00 -- 106.95 -45.00-120.00 51 13 \w 79.00 109.00 1.00 1.00 -- 106.95 -95.00 -60.00 30 14 \w 44.00 108.00 1.00 1.00 -- 106.95 -95.00 30.00 64 15 \w 60.00 103.00 1.00 1.00 -- 106.95 -95.00 120.00 43 16 \w 47.00 130.00 1.00 1.00 -- 106.95 -45.00 0.00 83 17 \w 41.00 121.00 1.00 1.00 -- 106.95-125.00 -60.00 80 18 \w -115.00 -16.00 1.00 1.00 -- -40.73 -38.00-150.00 99 ; _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 -0.1955539000 _diffrn_orient_matrix_UB_12 -0.0722113000 _diffrn_orient_matrix_UB_13 0.0442336000 _diffrn_orient_matrix_UB_21 -0.1098218000 _diffrn_orient_matrix_UB_22 0.1778479000 _diffrn_orient_matrix_UB_23 0.0001700000 _diffrn_orient_matrix_UB_31 -0.1042735000 _diffrn_orient_matrix_UB_32 -0.0117916000 _diffrn_orient_matrix_UB_33 -0.0693388000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0882 _diffrn_reflns_av_unetI/netI 0.0801 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 5808 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 66.599 _diffrn_reflns_theta_max 66.599 _diffrn_reflns_theta_min 2.359 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.365 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.18357 _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 1.637 _exptl_crystal_description block _exptl_crystal_F_000 476 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.906 _refine_diff_density_min -1.187 _refine_diff_density_rms 0.171 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 281 _refine_ls_number_reflns 3370 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.087 _refine_ls_R_factor_all 0.1060 _refine_ls_R_factor_gt 0.0955 _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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2680 _refine_ls_wR_factor_ref 0.2865 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2707 _reflns_number_total 3370 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03717g2.cif _cod_data_source_block 3004 _cod_database_code 7247704 _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 N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C14(H14), C15(H15), C17(H17), C18(H18) 2.b Idealised Me refined as rotating group: C19(H19A,H19B,H19C) ; _shelx_res_file ; TITL 3004_a.res in P-1 3004.res created by SHELXL-2018/3 at 11:43:28 on 07-Jul-2023 REM Old TITL 3004 in P-1 REM SHELXT solution in P-1: R1 0.239, Rweak 0.013, Alpha 0.052 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C22 N O7 Cl CELL 1.54184 6.2755 8.141 19.0094 81.051 85.123 84.276 ZERR 2 0.001 0.0009 0.0012 0.007 0.009 0.011 LATT 1 SFAC C H F N O S UNIT 38 28 14 2 6 2 L.S. 20 PLAN 5 TEMP -120 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta SHEL 999 0.84 REM REM REM WGHT 0.200000 FVAR 0.79767 S1 6 0.690929 0.687839 0.107057 11.00000 0.03223 0.01182 = 0.01364 0.00305 -0.00536 0.00049 O1 5 0.414609 0.381197 0.266442 11.00000 0.04290 0.03039 = 0.02232 0.00346 -0.00948 -0.01281 F2 3 0.479669 0.130555 0.371054 11.00000 0.05508 0.01703 = 0.03557 0.00303 0.00204 -0.00280 F3 3 0.671954 0.277790 0.423145 11.00000 0.03391 0.04297 = 0.03479 0.01918 -0.01447 -0.00505 F4 3 0.321529 0.490617 0.447522 11.00000 0.06951 0.02295 = 0.04127 -0.00141 0.00462 0.00066 F5 3 0.125573 0.345467 0.395386 11.00000 0.03260 0.06047 = 0.03596 0.01227 -0.00645 0.00127 F6 3 0.226308 0.072581 0.494326 11.00000 0.09713 0.03308 = 0.05370 0.01136 0.01538 -0.02289 F7 3 0.413977 0.215944 0.545775 11.00000 0.08094 0.07173 = 0.02749 0.01828 -0.01496 -0.00431 F8 3 0.078677 0.288307 0.537520 11.00000 0.07571 0.07060 = 0.04707 0.01623 0.02724 0.01529 O3 5 0.814345 0.829751 0.100005 11.00000 0.04533 0.01414 = 0.01965 0.00382 -0.00161 -0.00295 O2 5 0.509713 0.689489 0.066675 11.00000 0.03527 0.02234 = 0.01746 0.00074 -0.00947 0.00464 N1 4 0.588099 0.652123 0.192698 11.00000 0.02549 0.02206 = 0.01828 0.00137 -0.00255 -0.00151 AFIX 43 H1 2 0.452697 0.630275 0.199219 11.00000 -1.20000 AFIX 0 C1 1 0.832461 0.790758 0.256803 11.00000 0.03476 0.01907 = 0.01228 0.00244 -0.00066 -0.00639 C2 1 0.757518 0.953484 0.234913 11.00000 0.03606 0.01967 = 0.01708 -0.00085 -0.00290 -0.00375 AFIX 43 H2 2 0.624330 0.979066 0.213613 11.00000 -1.20000 AFIX 0 C3 1 0.881607 1.080939 0.244655 11.00000 0.04957 0.01806 = 0.02635 -0.00247 0.00219 -0.00507 AFIX 43 H3 2 0.831703 1.194239 0.230204 11.00000 -1.20000 AFIX 0 C4 1 1.076063 1.043034 0.275131 11.00000 0.04705 0.03174 = 0.02648 -0.00373 0.00022 -0.02122 AFIX 43 H4 2 1.159058 1.130588 0.281202 11.00000 -1.20000 AFIX 0 C5 1 1.151440 0.878260 0.296980 11.00000 0.04264 0.04370 = 0.02466 0.00097 -0.01056 -0.01118 AFIX 43 H5 2 1.285891 0.852524 0.317455 11.00000 -1.20000 AFIX 0 C6 1 1.025957 0.750350 0.288352 11.00000 0.04162 0.02457 = 0.02606 0.00139 -0.00951 -0.00655 AFIX 43 H6 2 1.073134 0.637011 0.303988 11.00000 -1.20000 AFIX 0 C7 1 0.692279 0.653485 0.252855 11.00000 0.03211 0.01418 = 0.01735 -0.00126 -0.00272 -0.00025 C8 1 0.656439 0.537398 0.312614 11.00000 0.03521 0.02236 = 0.01764 0.00289 -0.00802 -0.00314 AFIX 43 H8 2 0.724643 0.545434 0.354541 11.00000 -1.20000 AFIX 0 C9 1 0.521289 0.405580 0.314270 11.00000 0.03331 0.02028 = 0.01604 0.00296 -0.00359 -0.00264 C10 1 0.497016 0.283777 0.385522 11.00000 0.03763 0.01680 = 0.01977 0.00521 -0.00648 -0.00135 C11 1 0.299118 0.337569 0.432382 11.00000 0.04000 0.02176 = 0.02162 0.00669 -0.00547 -0.00312 C12 1 0.253750 0.224058 0.504373 11.00000 0.05173 0.03661 = 0.02660 0.00980 0.00637 0.00064 C13 1 0.862143 0.507816 0.097982 11.00000 0.02673 0.01405 = 0.01543 0.00150 -0.00397 0.00374 C14 1 0.791952 0.384525 0.064252 11.00000 0.03156 0.01993 = 0.01707 0.00100 -0.01070 -0.00142 AFIX 43 H14 2 0.654871 0.398632 0.045341 11.00000 -1.20000 AFIX 0 C15 1 0.928515 0.239860 0.059027 11.00000 0.04248 0.01442 = 0.02103 -0.00141 -0.00916 -0.00234 AFIX 43 H15 2 0.883517 0.154806 0.036121 11.00000 -1.20000 AFIX 0 C16 1 1.129650 0.218105 0.086831 11.00000 0.03657 0.01517 = 0.01610 0.00353 -0.00423 0.00127 C17 1 1.194377 0.344496 0.119156 11.00000 0.03385 0.02188 = 0.02403 -0.00047 -0.00865 -0.00151 AFIX 43 H17 2 1.331536 0.330633 0.138007 11.00000 -1.20000 AFIX 0 C18 1 1.063346 0.491505 0.124723 11.00000 0.02827 0.02054 = 0.02288 -0.00429 -0.00658 -0.00105 AFIX 43 H18 2 1.110608 0.577990 0.146222 11.00000 -1.20000 AFIX 0 C19 1 1.271171 0.059013 0.083957 11.00000 0.04091 0.02234 = 0.02682 0.00270 -0.00518 0.01280 AFIX 137 H19A 2 1.223812 -0.026653 0.122654 11.00000 -1.50000 H19B 2 1.419989 0.078758 0.089416 11.00000 -1.50000 H19C 2 1.262101 0.021076 0.037924 11.00000 -1.50000 AFIX 0 HKLF 4 REM 3004_a.res in P-1 REM wR2 = 0.2865, GooF = S = 1.087, Restrained GooF = 1.087 for all data REM R1 = 0.0955 for 2707 Fo > 4sig(Fo) and 0.1060 for all 3370 data REM 281 parameters refined using 0 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 0.906, deepest hole -1.187, 1-sigma level 0.171 Q1 1 0.7230 0.5662 0.1227 11.00000 0.05 0.91 Q2 1 0.7202 0.6257 0.1624 11.00000 0.05 0.74 Q3 1 0.6004 0.7067 0.1468 11.00000 0.05 0.73 Q4 1 0.6394 0.6780 0.1537 11.00000 0.05 0.73 Q5 1 0.8417 0.6224 0.0786 11.00000 0.05 0.71 ; _shelx_res_checksum 85108 _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 - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 3.707 _oxdiff_exptl_absorpt_empirical_full_min 0.312 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -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 0.69093(15) 0.68784(10) 0.10706(4) 0.0197(4) Uani 1 1 d . . . . . O1 O 0.4146(5) 0.3812(4) 0.26644(15) 0.0316(8) Uani 1 1 d . . . . . F2 F 0.4797(5) 0.1306(3) 0.37105(13) 0.0370(7) Uani 1 1 d . . . . . F3 F 0.6720(4) 0.2778(3) 0.42314(14) 0.0391(7) Uani 1 1 d . . . . . F4 F 0.3215(5) 0.4906(3) 0.44752(14) 0.0458(8) Uani 1 1 d . . . . . F5 F 0.1256(4) 0.3455(4) 0.39539(14) 0.0452(8) Uani 1 1 d . . . . . F6 F 0.2263(6) 0.0726(4) 0.49433(17) 0.0632(10) Uani 1 1 d . . . . . F7 F 0.4140(6) 0.2159(5) 0.54578(15) 0.0623(10) Uani 1 1 d . . . . . F8 F 0.0787(6) 0.2883(5) 0.53752(17) 0.0704(12) Uani 1 1 d . . . . . O3 O 0.8143(5) 0.8298(3) 0.10000(13) 0.0271(7) Uani 1 1 d . . . . . O2 O 0.5097(5) 0.6895(3) 0.06668(13) 0.0255(7) Uani 1 1 d . . . . . N1 N 0.5881(5) 0.6521(4) 0.19270(16) 0.0224(7) Uani 1 1 d . . . . . H1 H 0.452697 0.630275 0.199219 0.027 Uiso 1 1 calc R U . . . C1 C 0.8325(7) 0.7908(5) 0.25680(19) 0.0223(9) Uani 1 1 d . . . . . C2 C 0.7575(7) 0.9535(5) 0.2349(2) 0.0243(9) Uani 1 1 d . . . . . H2 H 0.624330 0.979066 0.213613 0.029 Uiso 1 1 calc R U . . . C3 C 0.8816(8) 1.0809(5) 0.2447(2) 0.0316(10) Uani 1 1 d . . . . . H3 H 0.831703 1.194239 0.230204 0.038 Uiso 1 1 calc R U . . . C4 C 1.0761(8) 1.0430(6) 0.2751(2) 0.0341(11) Uani 1 1 d . . . . . H4 H 1.159058 1.130588 0.281202 0.041 Uiso 1 1 calc R U . . . C5 C 1.1514(8) 0.8783(6) 0.2970(2) 0.0367(11) Uani 1 1 d . . . . . H5 H 1.285891 0.852524 0.317455 0.044 Uiso 1 1 calc R U . . . C6 C 1.0260(7) 0.7503(5) 0.2884(2) 0.0306(10) Uani 1 1 d . . . . . H6 H 1.073134 0.637011 0.303988 0.037 Uiso 1 1 calc R U . . . C7 C 0.6923(6) 0.6535(5) 0.25285(19) 0.0214(8) Uani 1 1 d . . . . . C8 C 0.6564(7) 0.5374(5) 0.3126(2) 0.0253(9) Uani 1 1 d . . . . . H8 H 0.724643 0.545434 0.354541 0.030 Uiso 1 1 calc R U . . . C9 C 0.5213(7) 0.4056(5) 0.31427(19) 0.0237(9) Uani 1 1 d . . . . . C10 C 0.4970(7) 0.2838(5) 0.3855(2) 0.0254(9) Uani 1 1 d . . . . . C11 C 0.2991(7) 0.3376(5) 0.4324(2) 0.0286(10) Uani 1 1 d . . . . . C12 C 0.2537(9) 0.2241(6) 0.5044(2) 0.0407(12) Uani 1 1 d . . . . . C13 C 0.8621(6) 0.5078(5) 0.09798(18) 0.0194(8) Uani 1 1 d . . . . . C14 C 0.7920(7) 0.3845(5) 0.06425(19) 0.0228(9) Uani 1 1 d . . . . . H14 H 0.654871 0.398632 0.045341 0.027 Uiso 1 1 calc R U . . . C15 C 0.9285(7) 0.2399(5) 0.0590(2) 0.0257(9) Uani 1 1 d . . . . . H15 H 0.883517 0.154806 0.036121 0.031 Uiso 1 1 calc R U . . . C16 C 1.1296(7) 0.2181(5) 0.08683(19) 0.0233(9) Uani 1 1 d . . . . . C17 C 1.1944(7) 0.3445(5) 0.1192(2) 0.0266(9) Uani 1 1 d . . . . . H17 H 1.331536 0.330633 0.138007 0.032 Uiso 1 1 calc R U . . . C18 C 1.0633(6) 0.4915(5) 0.1247(2) 0.0236(8) Uani 1 1 d . . . . . H18 H 1.110608 0.577990 0.146222 0.028 Uiso 1 1 calc R U . . . C19 C 1.2712(7) 0.0590(5) 0.0840(2) 0.0316(10) Uani 1 1 d . . . . . H19A H 1.223812 -0.026653 0.122654 0.047 Uiso 1 1 calc R U . . . H19B H 1.419989 0.078758 0.089416 0.047 Uiso 1 1 calc R U . . . H19C H 1.262101 0.021076 0.037924 0.047 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 0.0322(7) 0.0118(6) 0.0136(6) 0.0030(4) -0.0054(4) 0.0005(4) O1 0.0429(18) 0.0304(17) 0.0223(15) 0.0035(12) -0.0095(13) -0.0128(14) F2 0.0551(17) 0.0170(13) 0.0356(14) 0.0030(10) 0.0020(12) -0.0028(11) F3 0.0339(14) 0.0430(17) 0.0348(14) 0.0192(11) -0.0145(11) -0.0050(12) F4 0.070(2) 0.0230(14) 0.0413(16) -0.0014(11) 0.0046(14) 0.0007(13) F5 0.0326(15) 0.060(2) 0.0360(15) 0.0123(13) -0.0065(11) 0.0013(13) F6 0.097(3) 0.0331(18) 0.0537(19) 0.0114(14) 0.0154(18) -0.0229(17) F7 0.081(2) 0.072(2) 0.0275(15) 0.0183(14) -0.0150(15) -0.0043(19) F8 0.076(2) 0.071(3) 0.0471(18) 0.0162(16) 0.0272(17) 0.0153(19) O3 0.0453(18) 0.0141(14) 0.0196(14) 0.0038(10) -0.0016(12) -0.0029(12) O2 0.0353(17) 0.0223(15) 0.0175(13) 0.0007(10) -0.0095(12) 0.0046(12) N1 0.0255(17) 0.0221(17) 0.0183(16) 0.0014(12) -0.0026(13) -0.0015(13) C1 0.035(2) 0.019(2) 0.0123(17) 0.0024(14) -0.0007(15) -0.0064(16) C2 0.036(2) 0.020(2) 0.0171(18) -0.0009(14) -0.0029(15) -0.0038(16) C3 0.050(3) 0.018(2) 0.026(2) -0.0025(16) 0.0022(19) -0.0051(18) C4 0.047(3) 0.032(2) 0.026(2) -0.0037(17) 0.0002(18) -0.021(2) C5 0.043(3) 0.044(3) 0.025(2) 0.0010(19) -0.0106(19) -0.011(2) C6 0.042(3) 0.025(2) 0.026(2) 0.0014(17) -0.0095(18) -0.0065(18) C7 0.032(2) 0.0142(19) 0.0173(18) -0.0013(14) -0.0027(15) -0.0003(15) C8 0.035(2) 0.022(2) 0.0176(18) 0.0029(15) -0.0080(15) -0.0031(16) C9 0.033(2) 0.020(2) 0.0160(19) 0.0030(15) -0.0036(16) -0.0026(16) C10 0.038(2) 0.0168(19) 0.0198(19) 0.0052(15) -0.0065(16) -0.0014(16) C11 0.040(3) 0.022(2) 0.022(2) 0.0067(16) -0.0055(17) -0.0031(18) C12 0.052(3) 0.037(3) 0.027(2) 0.0098(19) 0.006(2) 0.001(2) C13 0.027(2) 0.0141(18) 0.0154(17) 0.0015(13) -0.0040(14) 0.0037(14) C14 0.032(2) 0.020(2) 0.0171(18) 0.0010(14) -0.0107(15) -0.0014(15) C15 0.042(2) 0.0144(19) 0.0210(19) -0.0014(14) -0.0092(17) -0.0023(16) C16 0.037(2) 0.0152(18) 0.0161(17) 0.0035(14) -0.0042(16) 0.0013(16) C17 0.034(2) 0.022(2) 0.024(2) -0.0005(15) -0.0086(16) -0.0015(17) C18 0.028(2) 0.021(2) 0.0229(19) -0.0043(15) -0.0066(15) -0.0010(15) C19 0.041(3) 0.022(2) 0.027(2) 0.0027(16) -0.0052(18) 0.0128(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 O3 S1 N1 107.66(16) . . ? O3 S1 C13 109.78(18) . . ? O2 S1 O3 121.49(17) . . ? O2 S1 N1 103.57(17) . . ? O2 S1 C13 109.22(17) . . ? N1 S1 C13 103.47(16) . . ? S1 N1 H1 116.4 . . ? C7 N1 S1 127.1(3) . . ? C7 N1 H1 116.4 . . ? C2 C1 C6 121.7(4) . . ? C2 C1 C7 119.2(4) . . ? C6 C1 C7 118.8(3) . . ? C1 C2 H2 120.7 . . ? C1 C2 C3 118.6(4) . . ? C3 C2 H2 120.7 . . ? C2 C3 H3 119.8 . . ? C4 C3 C2 120.5(4) . . ? C4 C3 H3 119.8 . . ? C3 C4 H4 119.7 . . ? C3 C4 C5 120.7(4) . . ? C5 C4 H4 119.7 . . ? C4 C5 H5 120.5 . . ? C4 C5 C6 119.0(4) . . ? C6 C5 H5 120.5 . . ? C1 C6 C5 119.5(4) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? N1 C7 C1 120.3(3) . . ? N1 C7 C8 120.5(4) . . ? C8 C7 C1 119.1(3) . . ? C7 C8 H8 118.6 . . ? C7 C8 C9 122.9(3) . . ? C9 C8 H8 118.6 . . ? O1 C9 C8 127.1(3) . . ? O1 C9 C10 115.8(4) . . ? C8 C9 C10 117.0(3) . . ? F2 C10 F3 108.1(3) . . ? F2 C10 C9 109.2(3) . . ? F2 C10 C11 109.3(4) . . ? F3 C10 C9 110.5(3) . . ? F3 C10 C11 108.1(3) . . ? C11 C10 C9 111.6(3) . . ? F4 C11 C10 108.4(4) . . ? F4 C11 C12 107.1(4) . . ? F5 C11 F4 108.8(3) . . ? F5 C11 C10 108.5(3) . . ? F5 C11 C12 107.1(4) . . ? C10 C11 C12 116.7(4) . . ? F6 C12 F7 108.3(4) . . ? F6 C12 F8 109.5(5) . . ? F6 C12 C11 111.1(4) . . ? F7 C12 F8 108.2(4) . . ? F7 C12 C11 111.0(4) . . ? F8 C12 C11 108.7(4) . . ? C14 C13 S1 119.0(3) . . ? C18 C13 S1 119.1(3) . . ? C18 C13 C14 121.9(3) . . ? C13 C14 H14 120.9 . . ? C13 C14 C15 118.3(4) . . ? C15 C14 H14 120.9 . . ? C14 C15 H15 119.4 . . ? C16 C15 C14 121.2(4) . . ? C16 C15 H15 119.4 . . ? C15 C16 C19 120.8(4) . . ? C17 C16 C15 118.7(3) . . ? C17 C16 C19 120.4(4) . . ? C16 C17 H17 119.1 . . ? C16 C17 C18 121.7(4) . . ? C18 C17 H17 119.1 . . ? C13 C18 C17 118.1(4) . . ? C13 C18 H18 120.9 . . ? C17 C18 H18 120.9 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 O3 1.437(3) . ? S1 O2 1.423(3) . ? S1 N1 1.692(3) . ? S1 C13 1.751(4) . ? O1 C9 1.225(5) . ? F2 C10 1.335(5) . ? F3 C10 1.353(5) . ? F4 C11 1.345(5) . ? F5 C11 1.337(5) . ? F6 C12 1.307(6) . ? F7 C12 1.319(6) . ? F8 C12 1.322(6) . ? N1 H1 0.8800 . ? N1 C7 1.367(5) . ? C1 C2 1.374(5) . ? C1 C6 1.387(6) . ? C1 C7 1.504(5) . ? C2 H2 0.9500 . ? C2 C3 1.401(6) . ? C3 H3 0.9500 . ? C3 C4 1.382(7) . ? C4 H4 0.9500 . ? C4 C5 1.389(7) . ? C5 H5 0.9500 . ? C5 C6 1.404(6) . ? C6 H6 0.9500 . ? C7 C8 1.378(5) . ? C8 H8 0.9500 . ? C8 C9 1.428(6) . ? C9 C10 1.555(5) . ? C10 C11 1.534(6) . ? C11 C12 1.549(6) . ? C13 C14 1.396(5) . ? C13 C18 1.387(5) . ? C14 H14 0.9500 . ? C14 C15 1.397(6) . ? C15 H15 0.9500 . ? C15 C16 1.394(6) . ? C16 C17 1.387(6) . ? C16 C19 1.501(5) . ? C17 H17 0.9500 . ? C17 C18 1.396(6) . ? C18 H18 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 N1 C7 C1 44.7(5) . . . . ? S1 N1 C7 C8 -140.6(3) . . . . ? S1 C13 C14 C15 -178.4(3) . . . . ? S1 C13 C18 C17 177.8(3) . . . . ? O1 C9 C10 F2 37.8(5) . . . . ? O1 C9 C10 F3 156.5(4) . . . . ? O1 C9 C10 C11 -83.2(5) . . . . ? F2 C10 C11 F4 178.8(3) . . . . ? F2 C10 C11 F5 -63.2(4) . . . . ? F2 C10 C11 C12 57.8(5) . . . . ? F3 C10 C11 F4 61.4(4) . . . . ? F3 C10 C11 F5 179.4(3) . . . . ? F3 C10 C11 C12 -59.6(5) . . . . ? F4 C11 C12 F6 179.0(4) . . . . ? F4 C11 C12 F7 -60.5(5) . . . . ? F4 C11 C12 F8 58.4(5) . . . . ? F5 C11 C12 F6 62.5(5) . . . . ? F5 C11 C12 F7 -177.0(4) . . . . ? F5 C11 C12 F8 -58.1(5) . . . . ? O3 S1 N1 C7 -43.9(4) . . . . ? O3 S1 C13 C14 -144.6(3) . . . . ? O3 S1 C13 C18 35.6(3) . . . . ? O2 S1 N1 C7 -173.8(3) . . . . ? O2 S1 C13 C14 -9.1(4) . . . . ? O2 S1 C13 C18 171.1(3) . . . . ? N1 S1 C13 C14 100.7(3) . . . . ? N1 S1 C13 C18 -79.0(3) . . . . ? N1 C7 C8 C9 3.6(6) . . . . ? C1 C2 C3 C4 0.5(6) . . . . ? C1 C7 C8 C9 178.3(4) . . . . ? C2 C1 C6 C5 -1.3(6) . . . . ? C2 C1 C7 N1 46.3(5) . . . . ? C2 C1 C7 C8 -128.4(4) . . . . ? C2 C3 C4 C5 -0.3(6) . . . . ? C3 C4 C5 C6 -0.7(7) . . . . ? C4 C5 C6 C1 1.5(6) . . . . ? C6 C1 C2 C3 0.3(6) . . . . ? C6 C1 C7 N1 -139.4(4) . . . . ? C6 C1 C7 C8 45.9(5) . . . . ? C7 C1 C2 C3 174.5(3) . . . . ? C7 C1 C6 C5 -175.5(4) . . . . ? C7 C8 C9 O1 -3.4(7) . . . . ? C7 C8 C9 C10 179.8(4) . . . . ? C8 C9 C10 F2 -145.0(4) . . . . ? C8 C9 C10 F3 -26.3(5) . . . . ? C8 C9 C10 C11 94.0(5) . . . . ? C9 C10 C11 F4 -60.4(4) . . . . ? C9 C10 C11 F5 57.6(4) . . . . ? C9 C10 C11 C12 178.7(4) . . . . ? C10 C11 C12 F6 -59.3(6) . . . . ? C10 C11 C12 F7 61.2(6) . . . . ? C10 C11 C12 F8 -179.9(4) . . . . ? C13 S1 N1 C7 72.3(4) . . . . ? C13 C14 C15 C16 0.2(6) . . . . ? C14 C13 C18 C17 -2.0(6) . . . . ? C14 C15 C16 C17 -1.0(6) . . . . ? C14 C15 C16 C19 177.2(4) . . . . ? C15 C16 C17 C18 0.3(6) . . . . ? C16 C17 C18 C13 1.1(6) . . . . ? C18 C13 C14 C15 1.3(6) . . . . ? C19 C16 C17 C18 -177.9(4) . . . . ?