#------------------------------------------------------------------------------ #$Date: 2025-02-13 04:12:46 +0200 (Thu, 13 Feb 2025) $ #$Revision: 297716 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573894.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_1573894 loop_ _publ_author_name 'Yu, Yongjiang' 'Chen, Wang' 'Hu, Rongrong' 'Tang, Ben Zhong' _publ_section_title ; Base-free Multicomponent Polymerization of Elemental Sulfur, Difluoromethylene Phosphobetaine and Amines Toward Electron-Deficient Aromatic Polythioureas ; _journal_name_full 'Polymer Chemistry' _journal_paper_doi 10.1039/D4PY01387E _journal_year 2024 _chemical_formula_moiety 'C15 H10 F6 N2 S' _chemical_formula_sum 'C15 H10 F6 N2 S' _chemical_formula_weight 364.31 _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 2024-09-20 _audit_creation_method ; Olex2 1.5 (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _audit_update_record ; 2024-12-03 deposited with the CCDC. 2025-02-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.715(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.2700(3) _cell_length_b 7.5957(2) _cell_length_c 14.4949(3) _cell_measurement_reflns_used 5159 _cell_measurement_temperature 302.36(10) _cell_measurement_theta_max 73.2650 _cell_measurement_theta_min 6.2850 _cell_volume 1532.58(6) _computing_cell_refinement 'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment air _diffrn_ambient_temperature 302.36(10) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.961 _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 18.00 43.00 0.50 0.50 -- 5.00 8.00 -82.00 50 2 \w -57.00 -32.00 0.50 0.50 -- 5.00 -8.00 105.00 50 3 \w -98.00 -60.00 0.50 0.50 -- -98.80 8.00 -82.00 76 4 \w -45.00 13.00 0.50 0.50 -- 0.00 -37.00-120.00 116 5 \w -46.00 9.00 0.50 0.50 -- 0.00 -57.00-150.00 110 6 \w -79.00 -53.00 0.50 0.50 -- 0.00 -37.00-120.00 52 7 \w 17.00 42.00 0.50 0.50 -- 5.00 72.00 60.00 50 8 \w -46.00 14.00 0.50 0.50 -- 5.00 -72.00 -30.00 120 9 \w -113.00 -9.00 0.50 0.50 -- -98.80 57.00 30.00 208 10 \w -130.00-104.00 0.50 0.50 -- -98.80 -19.00 -60.00 52 11 \w -109.00 -68.00 0.50 0.50 -- -98.80 19.00 120.00 82 12 \w -64.00 -23.00 0.50 0.50 -- -98.80 57.00 -60.00 82 13 \w -106.00 -81.00 0.50 0.50 -- -98.80 57.00 -60.00 50 14 \w -110.00 -25.00 0.50 0.50 -- -98.80 72.00 60.00 170 15 \w -188.00-111.00 0.50 0.50 -- -98.80 -19.00-120.00 154 16 \w -58.00 -9.00 0.50 0.50 -- -98.80 19.00 120.00 98 17 \w -104.00 -12.00 0.50 0.50 -- -98.80 19.00 30.00 184 18 \w -109.00 -83.00 0.50 0.50 -- -98.80 72.00 0.00 52 19 \w -98.00 -22.00 0.50 0.50 -- -98.80 72.00 120.00 152 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RCD3): Kappa single' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0163944000 _diffrn_orient_matrix_UB_12 0.0219031000 _diffrn_orient_matrix_UB_13 0.1009160000 _diffrn_orient_matrix_UB_21 0.1093783000 _diffrn_orient_matrix_UB_22 0.0088903000 _diffrn_orient_matrix_UB_23 0.0390052000 _diffrn_orient_matrix_UB_31 -0.0029695000 _diffrn_orient_matrix_UB_32 0.2015183000 _diffrn_orient_matrix_UB_33 -0.0127171000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_unetI/netI 0.0193 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.961 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 9056 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.961 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.583 _diffrn_reflns_theta_min 3.175 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.521 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.78535 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.579 _exptl_crystal_description cube _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.612 _refine_diff_density_min -0.579 _refine_diff_density_rms 0.073 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 219 _refine_ls_number_reflns 2973 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.089 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0602 _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^)+(0.0944P)^2^+0.9685P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1760 _refine_ls_wR_factor_ref 0.1795 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2675 _reflns_number_total 2973 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4py01387e2.cif _cod_data_source_block 1_1 _cod_database_code 1573894 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.787 _shelx_estimated_absorpt_t_min 0.752 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups 2.a Aromatic/amide H refined with riding coordinates: N1(H1), N2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14) ; _shelx_res_file ; TITL 1_1_a.res in P2(1)/c 1_1.res created by SHELXL-2018/3 at 19:25:52 on 20-Sep-2024 REM Old TITL 1_1 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.257, Rweak 0.039, Alpha 0.048 REM 0.473 for 233 systematic absences, Orientation as input REM Formula found by SHELXT: C21 N2 Cl CELL 1.54184 14.27 7.5957 14.4949 90 102.715 90 ZERR 4 0.0003 0.0002 0.0003 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N S UNIT 60 40 24 8 4 L.S. 30 0 0 PLAN 5 SIZE 0.11 0.12 0.1 TEMP 29 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.094400 0.968500 SWAT 0.046883 0.8482 FVAR 0.47114 S1 5 0.420440 0.352663 0.616519 11.00000 0.05597 0.05696 = 0.04465 0.00270 0.00924 0.00207 F1 3 0.922434 0.294430 0.540493 11.00000 0.06481 0.20428 = 0.10898 0.01561 0.03092 -0.02363 F2 3 0.842651 0.164757 0.421047 11.00000 0.14110 0.13374 = 0.15081 -0.05385 0.10507 -0.03388 F3 3 0.819579 0.430807 0.439608 11.00000 0.12194 0.11821 = 0.14907 0.05283 0.08119 0.01642 F4 3 0.017004 0.393321 0.800782 11.00000 0.15371 0.30508 = 0.28977 0.18467 0.14940 0.15244 F5 3 0.080701 0.337114 0.936321 11.00000 0.09464 0.27124 = 0.17693 -0.10513 0.06868 -0.00685 F6 3 0.013113 0.147673 0.850367 11.00000 0.11014 0.13814 = 0.28416 -0.04952 0.12592 -0.04048 N1 4 0.547425 0.099720 0.683403 11.00000 0.05869 0.06444 = 0.06042 0.01687 0.02367 0.01133 AFIX 43 H1 2 0.561458 0.008251 0.718710 11.00000 -1.20000 AFIX 0 N2 4 0.414788 0.099691 0.743496 11.00000 0.05642 0.06444 = 0.05762 0.01490 0.02086 0.00801 AFIX 43 H2 2 0.441024 0.006887 0.771993 11.00000 -1.20000 AFIX 0 C1 1 0.836394 0.281238 0.486091 11.00000 0.06955 0.08268 = 0.07190 0.00131 0.03017 0.00057 C2 1 0.760326 0.236399 0.538390 11.00000 0.05779 0.06101 = 0.05968 0.00108 0.02204 0.00363 C3 1 0.666605 0.216095 0.488810 11.00000 0.06596 0.07537 = 0.04814 0.00204 0.01823 -0.00047 AFIX 43 H3 2 0.651768 0.231366 0.423551 11.00000 -1.20000 AFIX 0 C4 1 0.594492 0.173366 0.534845 11.00000 0.05779 0.07187 = 0.05081 -0.00080 0.01342 -0.00310 AFIX 43 H4 2 0.531620 0.158714 0.500924 11.00000 -1.20000 AFIX 0 C5 1 0.617241 0.152612 0.632495 11.00000 0.05543 0.05352 = 0.05325 0.00482 0.01895 0.00622 C6 1 0.710436 0.172284 0.681276 11.00000 0.05875 0.09136 = 0.04796 0.00832 0.01242 0.00914 AFIX 43 H6 2 0.725674 0.156445 0.746493 11.00000 -1.20000 AFIX 0 C7 1 0.781714 0.215146 0.635027 11.00000 0.05259 0.09748 = 0.06154 -0.00074 0.01275 0.00494 AFIX 43 H7 2 0.844517 0.229804 0.669131 11.00000 -1.20000 AFIX 0 C8 1 0.461825 0.175572 0.683065 11.00000 0.05209 0.05540 = 0.03933 -0.00384 0.01062 -0.00210 C9 1 0.327242 0.153556 0.766163 11.00000 0.05189 0.05596 = 0.04958 0.00270 0.01564 -0.00322 C10 1 0.244147 0.183734 0.698708 11.00000 0.05813 0.09883 = 0.04636 0.00150 0.00917 -0.00545 AFIX 43 H10 2 0.244605 0.175277 0.634801 11.00000 -1.20000 AFIX 0 C11 1 0.160438 0.226452 0.726233 11.00000 0.04830 0.10158 = 0.06316 0.01065 0.00412 -0.00332 AFIX 43 H11 2 0.104582 0.247444 0.680690 11.00000 -1.20000 AFIX 0 C12 1 0.158989 0.238279 0.821040 11.00000 0.05288 0.06381 = 0.07113 0.00391 0.01966 -0.00273 C13 1 0.242117 0.206835 0.887921 11.00000 0.06183 0.08674 = 0.05070 -0.00051 0.01814 -0.00225 AFIX 43 H13 2 0.241705 0.214565 0.951864 11.00000 -1.20000 AFIX 0 C14 1 0.325577 0.164150 0.860738 11.00000 0.05354 0.07911 = 0.04625 0.00567 0.00881 0.00008 AFIX 43 H14 2 0.381261 0.142275 0.906353 11.00000 -1.20000 AFIX 0 C15 1 0.068268 0.281259 0.851254 11.00000 0.05899 0.09124 = 0.09144 0.00526 0.02747 0.00455 HKLF 4 REM 1_1_a.res in P2(1)/c REM wR2 = 0.1795, GooF = S = 1.089, Restrained GooF = 1.089 for all data REM R1 = 0.0602 for 2675 Fo > 4sig(Fo) and 0.0638 for all 2973 data REM 219 parameters refined using 0 restraints END WGHT 0.0945 0.9541 REM Highest difference peak 0.612, deepest hole -0.579, 1-sigma level 0.073 Q1 1 0.0638 0.4347 0.8701 11.00000 0.05 0.61 Q2 1 -0.0051 0.2530 0.7847 11.00000 0.05 0.58 Q3 1 0.0591 0.1933 0.9239 11.00000 0.05 0.56 Q4 1 0.8963 0.1559 0.5013 11.00000 0.05 0.30 Q5 1 0.0032 0.4426 0.8020 11.00000 0.05 0.28 ; _shelx_res_checksum 33292 _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 1.262 _oxdiff_exptl_absorpt_empirical_full_min 0.757 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 0.42044(5) 0.35266(9) 0.61652(4) 0.0528(3) Uani 1 1 d . . . . . F1 F 0.92243(16) 0.2944(5) 0.54049(19) 0.1242(11) Uani 1 1 d . . . . . F2 F 0.8427(2) 0.1648(4) 0.4210(2) 0.1306(12) Uani 1 1 d . . . . . F3 F 0.8196(2) 0.4308(4) 0.4396(2) 0.1218(10) Uani 1 1 d . . . . . F4 F 0.0170(3) 0.3933(7) 0.8008(4) 0.234(3) Uani 1 1 d . . . . . F5 F 0.0807(2) 0.3371(6) 0.9363(3) 0.1750(19) Uani 1 1 d . . . . . F6 F 0.0131(2) 0.1477(4) 0.8504(3) 0.1648(17) Uani 1 1 d . . . . . N1 N 0.54742(17) 0.0997(3) 0.68340(17) 0.0596(6) Uani 1 1 d . . . . . H1 H 0.561458 0.008251 0.718710 0.071 Uiso 1 1 calc R U . . . N2 N 0.41479(16) 0.0997(3) 0.74350(16) 0.0582(6) Uani 1 1 d . . . . . H2 H 0.441024 0.006887 0.771993 0.070 Uiso 1 1 calc R U . . . C1 C 0.8364(2) 0.2812(5) 0.4861(2) 0.0725(9) Uani 1 1 d . . . . . C2 C 0.7603(2) 0.2364(4) 0.5384(2) 0.0581(7) Uani 1 1 d . . . . . C3 C 0.6666(2) 0.2161(4) 0.4888(2) 0.0623(7) Uani 1 1 d . . . . . H3 H 0.651768 0.231366 0.423551 0.075 Uiso 1 1 calc R U . . . C4 C 0.5945(2) 0.1734(4) 0.5348(2) 0.0599(7) Uani 1 1 d . . . . . H4 H 0.531620 0.158714 0.500924 0.072 Uiso 1 1 calc R U . . . C5 C 0.6172(2) 0.1526(3) 0.63249(19) 0.0530(7) Uani 1 1 d . . . . . C6 C 0.7104(2) 0.1723(5) 0.6813(2) 0.0659(8) Uani 1 1 d . . . . . H6 H 0.725674 0.156445 0.746493 0.079 Uiso 1 1 calc R U . . . C7 C 0.7817(2) 0.2151(5) 0.6350(2) 0.0705(9) Uani 1 1 d . . . . . H7 H 0.844517 0.229804 0.669131 0.085 Uiso 1 1 calc R U . . . C8 C 0.46183(18) 0.1756(4) 0.68306(17) 0.0489(6) Uani 1 1 d . . . . . C9 C 0.32724(19) 0.1536(4) 0.76616(18) 0.0518(6) Uani 1 1 d . . . . . C10 C 0.2441(2) 0.1837(5) 0.6987(2) 0.0681(8) Uani 1 1 d . . . . . H10 H 0.244605 0.175277 0.634801 0.082 Uiso 1 1 calc R U . . . C11 C 0.1604(2) 0.2265(5) 0.7262(2) 0.0723(9) Uani 1 1 d . . . . . H11 H 0.104582 0.247444 0.680690 0.087 Uiso 1 1 calc R U . . . C12 C 0.1590(2) 0.2383(4) 0.8210(2) 0.0617(7) Uani 1 1 d . . . . . C13 C 0.2421(2) 0.2068(5) 0.8879(2) 0.0655(8) Uani 1 1 d . . . . . H13 H 0.241705 0.214565 0.951864 0.079 Uiso 1 1 calc R U . . . C14 C 0.3256(2) 0.1641(4) 0.86074(19) 0.0600(7) Uani 1 1 d . . . . . H14 H 0.381261 0.142275 0.906353 0.072 Uiso 1 1 calc R U . . . C15 C 0.0683(2) 0.2813(6) 0.8513(3) 0.0789(10) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0560(4) 0.0570(5) 0.0446(4) 0.0027(3) 0.0092(3) 0.0021(3) F1 0.0648(13) 0.204(3) 0.1090(19) 0.0156(19) 0.0309(13) -0.0236(16) F2 0.141(2) 0.134(2) 0.151(2) -0.0538(19) 0.105(2) -0.0339(17) F3 0.122(2) 0.118(2) 0.149(2) 0.0528(18) 0.0812(18) 0.0164(16) F4 0.154(3) 0.305(6) 0.290(5) 0.185(5) 0.149(4) 0.152(4) F5 0.095(2) 0.271(5) 0.177(3) -0.105(3) 0.069(2) -0.007(2) F6 0.110(2) 0.138(3) 0.284(5) -0.050(3) 0.126(3) -0.0405(18) N1 0.0587(13) 0.0644(14) 0.0604(13) 0.0169(11) 0.0237(10) 0.0113(11) N2 0.0564(13) 0.0644(14) 0.0576(13) 0.0149(11) 0.0209(10) 0.0080(11) C1 0.070(2) 0.083(2) 0.072(2) 0.0013(17) 0.0302(16) 0.0006(16) C2 0.0578(15) 0.0610(17) 0.0597(15) 0.0011(13) 0.0220(12) 0.0036(13) C3 0.0660(17) 0.0754(19) 0.0481(14) 0.0020(13) 0.0182(12) -0.0005(14) C4 0.0578(15) 0.0719(19) 0.0508(14) -0.0008(13) 0.0134(12) -0.0031(13) C5 0.0554(15) 0.0535(15) 0.0532(14) 0.0048(11) 0.0190(11) 0.0062(11) C6 0.0588(16) 0.091(2) 0.0480(14) 0.0083(14) 0.0124(12) 0.0091(15) C7 0.0526(16) 0.097(2) 0.0615(17) -0.0007(16) 0.0127(13) 0.0049(15) C8 0.0521(14) 0.0554(15) 0.0393(12) -0.0038(10) 0.0106(10) -0.0021(11) C9 0.0519(14) 0.0560(16) 0.0496(14) 0.0027(11) 0.0156(11) -0.0032(11) C10 0.0581(17) 0.099(2) 0.0464(14) 0.0015(15) 0.0092(12) -0.0054(15) C11 0.0483(15) 0.102(3) 0.0632(17) 0.0107(17) 0.0041(13) -0.0033(15) C12 0.0529(15) 0.0638(18) 0.0711(18) 0.0039(14) 0.0197(13) -0.0027(12) C13 0.0618(17) 0.087(2) 0.0507(15) -0.0005(14) 0.0181(13) -0.0023(15) C14 0.0535(15) 0.079(2) 0.0462(14) 0.0057(13) 0.0088(11) 0.0001(13) C15 0.0590(18) 0.091(3) 0.091(2) 0.005(2) 0.0275(17) 0.0045(17) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' 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 C5 N1 H1 116.0 . . ? C8 N1 H1 116.0 . . ? C8 N1 C5 127.9(2) . . ? C8 N2 H2 115.9 . . ? C8 N2 C9 128.2(2) . . ? C9 N2 H2 115.9 . . ? F1 C1 F2 106.4(3) . . ? F1 C1 F3 106.5(3) . . ? F1 C1 C2 113.7(3) . . ? F2 C1 F3 104.4(3) . . ? F2 C1 C2 112.5(3) . . ? F3 C1 C2 112.7(3) . . ? C3 C2 C1 119.4(3) . . ? C7 C2 C1 121.4(3) . . ? C7 C2 C3 119.3(3) . . ? C2 C3 H3 119.5 . . ? C2 C3 C4 120.9(3) . . ? C4 C3 H3 119.5 . . ? C3 C4 H4 120.5 . . ? C3 C4 C5 119.1(3) . . ? C5 C4 H4 120.5 . . ? C4 C5 N1 121.8(3) . . ? C6 C5 N1 118.3(2) . . ? C6 C5 C4 119.7(3) . . ? C5 C6 H6 119.6 . . ? C5 C6 C7 120.8(3) . . ? C7 C6 H6 119.6 . . ? C2 C7 H7 119.9 . . ? C6 C7 C2 120.1(3) . . ? C6 C7 H7 119.9 . . ? N1 C8 S1 123.1(2) . . ? N2 C8 S1 123.6(2) . . ? N2 C8 N1 113.3(2) . . ? C10 C9 N2 123.1(2) . . ? C14 C9 N2 117.1(2) . . ? C14 C9 C10 119.6(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 C9 119.9(3) . . ? C11 C10 H10 120.1 . . ? C10 C11 H11 119.8 . . ? C10 C11 C12 120.4(3) . . ? C12 C11 H11 119.8 . . ? C11 C12 C15 120.7(3) . . ? C13 C12 C11 119.3(3) . . ? C13 C12 C15 120.0(3) . . ? C12 C13 H13 119.8 . . ? C14 C13 C12 120.4(3) . . ? C14 C13 H13 119.8 . . ? C9 C14 H14 119.8 . . ? C13 C14 C9 120.3(3) . . ? C13 C14 H14 119.8 . . ? F4 C15 F5 106.1(5) . . ? F4 C15 F6 104.7(4) . . ? F4 C15 C12 114.3(3) . . ? F5 C15 F6 103.1(4) . . ? F5 C15 C12 114.2(3) . . ? F6 C15 C12 113.2(3) . . ? 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 C8 1.685(3) . ? F1 C1 1.309(4) . ? F2 C1 1.310(4) . ? F3 C1 1.316(4) . ? F4 C15 1.249(5) . ? F5 C15 1.279(5) . ? F6 C15 1.282(5) . ? N1 H1 0.8600 . ? N1 C5 1.422(3) . ? N1 C8 1.350(3) . ? N2 H2 0.8600 . ? N2 C8 1.345(3) . ? N2 C9 1.420(3) . ? C1 C2 1.494(4) . ? C2 C3 1.381(4) . ? C2 C7 1.376(4) . ? C3 H3 0.9300 . ? C3 C4 1.383(4) . ? C4 H4 0.9300 . ? C4 C5 1.390(4) . ? C5 C6 1.370(4) . ? C6 H6 0.9300 . ? C6 C7 1.375(4) . ? C7 H7 0.9300 . ? C9 C10 1.380(4) . ? C9 C14 1.379(4) . ? C10 H10 0.9300 . ? C10 C11 1.379(4) . ? C11 H11 0.9300 . ? C11 C12 1.382(4) . ? C12 C13 1.378(4) . ? C12 C15 1.491(4) . ? C13 H13 0.9300 . ? C13 C14 1.373(4) . ? 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 F1 C1 C2 C3 -179.0(3) . . . . ? F1 C1 C2 C7 1.1(5) . . . . ? F2 C1 C2 C3 -58.0(4) . . . . ? F2 C1 C2 C7 122.1(4) . . . . ? F3 C1 C2 C3 59.7(4) . . . . ? F3 C1 C2 C7 -120.2(4) . . . . ? N1 C5 C6 C7 176.9(3) . . . . ? N2 C9 C10 C11 176.5(3) . . . . ? N2 C9 C14 C13 -176.8(3) . . . . ? C1 C2 C3 C4 179.5(3) . . . . ? C1 C2 C7 C6 -179.4(3) . . . . ? C2 C3 C4 C5 0.7(5) . . . . ? C3 C2 C7 C6 0.7(5) . . . . ? C3 C4 C5 N1 -176.6(3) . . . . ? C3 C4 C5 C6 -0.9(4) . . . . ? C4 C5 C6 C7 1.0(5) . . . . ? C5 N1 C8 S1 1.5(4) . . . . ? C5 N1 C8 N2 -176.2(3) . . . . ? C5 C6 C7 C2 -1.0(5) . . . . ? C7 C2 C3 C4 -0.6(5) . . . . ? C8 N1 C5 C4 -55.0(4) . . . . ? C8 N1 C5 C6 129.2(3) . . . . ? C8 N2 C9 C10 53.0(4) . . . . ? C8 N2 C9 C14 -131.2(3) . . . . ? C9 N2 C8 S1 -2.9(4) . . . . ? C9 N2 C8 N1 174.9(3) . . . . ? C9 C10 C11 C12 -0.4(5) . . . . ? C10 C9 C14 C13 -0.9(5) . . . . ? C10 C11 C12 C13 0.0(5) . . . . ? C10 C11 C12 C15 -178.9(3) . . . . ? C11 C12 C13 C14 0.0(5) . . . . ? C11 C12 C15 F4 -38.5(6) . . . . ? C11 C12 C15 F5 -161.0(4) . . . . ? C11 C12 C15 F6 81.3(5) . . . . ? C12 C13 C14 C9 0.5(5) . . . . ? C13 C12 C15 F4 142.6(5) . . . . ? C13 C12 C15 F5 20.1(6) . . . . ? C13 C12 C15 F6 -97.5(5) . . . . ? C14 C9 C10 C11 0.8(5) . . . . ? C15 C12 C13 C14 178.9(3) . . . . ?