#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:01:35 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288801 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247709.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_7247709 loop_ _publ_author_name 'Madhesiya, Avinash' 'Dash, Sibananda G.' 'Gupta, Princi' 'Akhir, Abdul' 'Saxena, Deepanshi' 'Maitra, Rahul' 'Chopra, Sidharth' 'Thakur, Tejender S.' _publ_section_title ; Development of new multicomponent crystals of the antifungal drug tioconazole and the assessment of their biopharmaceutical attributes ; _journal_issue 48 _journal_name_full CrystEngComm _journal_page_first 6758 _journal_page_last 6776 _journal_paper_doi 10.1039/D3CE00948C _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C16 H14 Cl3 N2 O S, Br' _chemical_formula_sum 'C16 H14 Br Cl3 N2 O S' _chemical_formula_weight 468.61 _chemical_name_common 'Tioconazole Hydrobromide Salt' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2019/2 _audit_update_record ; 2023-07-31 deposited with the CCDC. 2023-11-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.246(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 35.9750(19) _cell_length_b 6.3852(4) _cell_length_c 17.1343(9) _cell_measurement_reflns_used 9573 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 78.09 _cell_measurement_theta_min 2.66 _cell_volume 3814.8(4) _computing_cell_refinement 'Bruker SAINT v8.37a' _computing_data_collection 'PROTEUM2,version 2016.1-RC1' _computing_data_reduction 'Bruker SAINT v8.37a' _computing_publication_material 'WinGX publication routines (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Bruker D8 VENTURE' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.1046 _diffrn_reflns_av_unetI/netI 0.0356 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 45 _diffrn_reflns_limit_h_min -45 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 54812 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 79.212 _diffrn_reflns_theta_min 5.073 _exptl_absorpt_coefficient_mu 7.882 _exptl_absorpt_correction_T_max 0.7542 _exptl_absorpt_correction_T_min 0.4192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS-2016/2 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.632 _exptl_crystal_description block _exptl_crystal_F_000 1872 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.625 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.072 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 231 _refine_ls_number_reflns 4093 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0478 _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^)+(0.0594P)^2^+7.5171P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1178 _refine_ls_wR_factor_ref 0.1306 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3106 _reflns_number_total 4093 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00948c2.cif _cod_data_source_block TCZ-BROM _cod_depositor_comments 'Adding full bibliography for 7247709--7247724.cif.' _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 7247709 _shelx_shelxl_version_number 2019/2 _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_min 0.201 _shelx_estimated_absorpt_t_max 0.405 _shelx_res_file ; TITL PG20200304l in C2/c shelx.res created by SHELXL-2019/2 at 15:26:43 on 21-Jul-2023 CELL 1.54178 35.9750 6.3852 17.1343 90.000 104.246 90.000 ZERR 8.00 0.0019 0.0004 0.0009 0.000 0.003 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H N O CL S BR UNIT 128 112 16 8 24 8 8 MERG 2 OMIT -17 1 2 FMAP 2 PLAN 2 SIZE 0.140 0.160 0.300 ACTA BOND $H CONF LIST 4 L.S. 10 TEMP 22.61 WGHT 0.059400 7.517100 FVAR 0.06522 0.45069 C1 1 0.409072 0.625793 0.498920 11.00000 0.03996 0.06112 = 0.03375 0.00364 0.01273 -0.00148 C2 1 0.438078 0.762256 0.495765 11.00000 0.06010 0.05791 = 0.04701 -0.00022 0.02424 -0.00986 C3 1 0.463679 0.726791 0.448993 11.00000 0.05898 0.08697 = 0.05731 -0.00113 0.02916 -0.02082 AFIX 43 H3 2 0.482989 0.822962 0.448137 11.00000 -1.20000 AFIX 0 C4 1 0.460230 0.551276 0.404802 11.00000 0.04228 0.09844 = 0.03892 0.00031 0.01535 0.00144 C5 1 0.431704 0.414042 0.404362 11.00000 0.08501 0.11211 = 0.09715 -0.05749 0.05752 -0.03795 AFIX 43 H5 2 0.429143 0.294645 0.372393 11.00000 -1.20000 AFIX 0 C6 1 0.406229 0.451239 0.451607 11.00000 0.07496 0.09881 = 0.09360 -0.04615 0.05230 -0.04186 AFIX 43 H6 2 0.386732 0.355264 0.451148 11.00000 -1.20000 AFIX 0 C7 1 0.380507 0.661474 0.548997 11.00000 0.04239 0.05277 = 0.03314 0.00495 0.01065 -0.00358 AFIX 13 H7 2 0.389549 0.774518 0.587700 11.00000 -1.20000 AFIX 0 C8 1 0.341799 0.719987 0.494339 11.00000 0.04682 0.06445 = 0.03851 0.00953 0.01196 0.00476 AFIX 23 H8A 2 0.343804 0.853858 0.468928 11.00000 -1.20000 H8B 2 0.334249 0.615536 0.452311 11.00000 -1.20000 AFIX 0 C9 1 0.288875 0.578729 0.545845 11.00000 0.04080 0.06152 = 0.04636 -0.00164 0.01004 0.00335 AFIX 43 H9 2 0.286497 0.453025 0.517631 11.00000 -1.20000 AFIX 0 C10 1 0.280669 0.827608 0.627472 11.00000 0.04933 0.08894 = 0.05814 -0.01606 0.01681 0.00787 AFIX 43 H10 2 0.271312 0.902274 0.665173 11.00000 -1.20000 AFIX 0 C11 1 0.307928 0.890486 0.592251 11.00000 0.04910 0.06546 = 0.06356 -0.01330 0.01127 0.00240 AFIX 43 H11 2 0.321223 1.016663 0.600885 11.00000 -1.20000 AFIX 0 C12 1 0.401550 0.445291 0.665195 11.00000 0.04969 0.06481 = 0.04647 0.01626 -0.00027 -0.00924 AFIX 23 H12A 2 0.408808 0.577900 0.692282 11.00000 -1.20000 H12B 2 0.424384 0.379016 0.656120 11.00000 -1.20000 AFIX 0 C13 1 0.397172 0.126105 0.750649 11.00000 0.05926 0.05719 = 0.03915 -0.00018 0.00915 -0.00885 C14 1 0.383008 0.306694 0.715147 11.00000 0.05232 0.05342 = 0.03667 0.00358 0.00369 -0.00757 C15 1 0.347063 0.350614 0.731672 11.00000 0.06157 0.06916 = 0.04578 0.00843 0.00691 0.00372 AFIX 43 H15 2 0.333043 0.471035 0.713557 11.00000 -1.20000 AFIX 0 C16 1 0.334931 0.202279 0.776047 11.00000 0.06343 0.08757 = 0.04474 0.00749 0.01656 -0.00398 AFIX 43 H16 2 0.311716 0.207539 0.790700 11.00000 -1.20000 AFIX 0 N1 3 0.312624 0.733176 0.540744 11.00000 0.03848 0.05926 = 0.04041 0.00062 0.00883 0.00491 N2 3 0.269084 0.634361 0.598126 11.00000 0.03833 0.07939 = 0.05527 -0.00070 0.01421 0.00150 O1 4 0.374045 0.477749 0.590574 11.00000 0.04405 0.05396 = 0.03636 0.00589 0.00836 -0.00874 CL1A 5 0.434038 1.012617 0.530234 21.00000 0.11389 0.06375 = 0.08993 -0.00402 0.05009 -0.02964 CL1B 5 0.450120 0.969423 0.567553 -21.00000 0.08981 0.08327 = 0.09245 -0.03880 0.05101 -0.04289 CL2 5 0.492091 0.503391 0.345195 11.00000 0.05990 0.14737 = 0.06127 -0.01146 0.03417 0.00110 CL3 5 0.440490 0.013203 0.751665 11.00000 0.07434 0.06937 = 0.07667 0.00937 0.02228 0.01172 S1 6 0.367449 0.004593 0.801773 11.00000 0.07569 0.06687 = 0.04798 0.01487 0.01561 -0.00766 BR1 7 0.208642 0.285511 0.621010 11.00000 0.07115 0.06288 = 0.08695 -0.01637 0.03943 -0.00333 H2N 2 0.252720 0.556560 0.609419 11.00000 0.06997 HKLF 4 REM PG20200304l in C2/c REM wR2 = 0.1306, GooF = S = 1.040, Restrained GooF = 1.040 for all data REM R1 = 0.0478 for 3106 Fo > 4sig(Fo) and 0.0675 for all 4093 data REM 231 parameters refined using 0 restraints END WGHT 0.0594 7.5173 REM Highest difference peak 0.625, deepest hole -0.393, 1-sigma level 0.072 Q1 1 0.2304 0.3388 0.6183 11.00000 0.05 0.62 Q2 1 0.2264 0.3863 0.6107 11.00000 0.05 0.57 ; _shelx_res_checksum 71971 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 C1 C 0.40907(9) 0.6258(6) 0.49892(18) 0.0443(7) Uani 1 1 d . . . . . C2 C 0.43808(11) 0.7623(6) 0.4958(2) 0.0531(9) Uani 1 1 d . . . . . C3 C 0.46368(12) 0.7268(7) 0.4490(2) 0.0652(11) Uani 1 1 d . . . . . H3 H 0.482989 0.822962 0.448137 0.078 Uiso 1 1 calc R U . . . C4 C 0.46023(10) 0.5513(7) 0.4048(2) 0.0589(10) Uani 1 1 d . . . . . C5 C 0.43170(14) 0.4140(9) 0.4044(3) 0.0920(18) Uani 1 1 d . . . . . H5 H 0.429143 0.294645 0.372393 0.110 Uiso 1 1 calc R U . . . C6 C 0.40623(13) 0.4512(8) 0.4516(3) 0.0836(16) Uani 1 1 d . . . . . H6 H 0.386732 0.355264 0.451148 0.100 Uiso 1 1 calc R U . . . C7 C 0.38051(9) 0.6615(5) 0.54900(18) 0.0425(7) Uani 1 1 d . . . . . H7 H 0.389549 0.774518 0.587700 0.051 Uiso 1 1 calc R U . . . C8 C 0.34180(9) 0.7200(6) 0.4943(2) 0.0497(8) Uani 1 1 d . . . . . H8A H 0.343804 0.853858 0.468928 0.060 Uiso 1 1 calc R U . . . H8B H 0.334249 0.615536 0.452311 0.060 Uiso 1 1 calc R U . . . C9 C 0.28887(9) 0.5787(6) 0.5458(2) 0.0497(8) Uani 1 1 d . . . . . H9 H 0.286497 0.453025 0.517631 0.060 Uiso 1 1 calc R U . . . C10 C 0.28067(11) 0.8276(7) 0.6275(2) 0.0648(11) Uani 1 1 d . . . . . H10 H 0.271312 0.902274 0.665173 0.078 Uiso 1 1 calc R U . . . C11 C 0.30793(10) 0.8905(7) 0.5923(2) 0.0598(9) Uani 1 1 d . . . . . H11 H 0.321223 1.016663 0.600885 0.072 Uiso 1 1 calc R U . . . C12 C 0.40155(10) 0.4453(6) 0.6652(2) 0.0558(9) Uani 1 1 d . . . . . H12A H 0.408808 0.577900 0.692282 0.067 Uiso 1 1 calc R U . . . H12B H 0.424384 0.379016 0.656120 0.067 Uiso 1 1 calc R U . . . C13 C 0.39717(11) 0.1261(6) 0.7506(2) 0.0524(8) Uani 1 1 d . . . . . C14 C 0.38301(10) 0.3067(6) 0.7151(2) 0.0487(8) Uani 1 1 d . . . . . C15 C 0.34706(11) 0.3506(7) 0.7317(2) 0.0599(9) Uani 1 1 d . . . . . H15 H 0.333043 0.471035 0.713557 0.072 Uiso 1 1 calc R U . . . C16 C 0.33493(12) 0.2023(7) 0.7760(2) 0.0647(10) Uani 1 1 d . . . . . H16 H 0.311716 0.207539 0.790700 0.078 Uiso 1 1 calc R U . . . N1 N 0.31262(7) 0.7332(5) 0.54074(16) 0.0462(6) Uani 1 1 d . . . . . N2 N 0.26908(8) 0.6344(6) 0.59813(19) 0.0572(8) Uani 1 1 d . . . . . O1 O 0.37405(6) 0.4777(4) 0.59057(13) 0.0451(5) Uani 1 1 d . . . . . Cl1A Cl 0.4340(5) 1.0126(7) 0.5302(9) 0.085(3) Uani 0.45(2) 1 d . . P . . Cl1B Cl 0.4501(3) 0.9694(16) 0.5676(8) 0.084(3) Uani 0.55(2) 1 d . . P . . Cl2 Cl 0.49209(3) 0.5034(2) 0.34520(7) 0.0861(4) Uani 1 1 d . . . . . Cl3 Cl 0.44049(3) 0.01320(18) 0.75166(7) 0.0728(3) Uani 1 1 d . . . . . S1 S 0.36745(3) 0.00459(17) 0.80177(6) 0.0634(3) Uani 1 1 d . . . . . Br1 Br 0.20864(2) 0.28551(7) 0.62101(3) 0.07017(18) Uani 1 1 d . . . . . H2N H 0.2527(13) 0.557(7) 0.609(3) 0.070(14) Uiso 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 C1 0.0400(15) 0.061(2) 0.0337(15) 0.0036(14) 0.0127(12) -0.0015(14) C2 0.060(2) 0.058(2) 0.0470(19) -0.0002(16) 0.0242(16) -0.0099(16) C3 0.059(2) 0.087(3) 0.057(2) -0.001(2) 0.0292(18) -0.021(2) C4 0.0423(17) 0.098(3) 0.0389(18) 0.0003(19) 0.0154(14) 0.0014(18) C5 0.085(3) 0.112(4) 0.097(4) -0.057(3) 0.058(3) -0.038(3) C6 0.075(3) 0.099(4) 0.094(3) -0.046(3) 0.052(3) -0.042(3) C7 0.0424(16) 0.0528(19) 0.0331(15) 0.0049(13) 0.0106(12) -0.0036(13) C8 0.0468(17) 0.064(2) 0.0385(16) 0.0095(15) 0.0120(14) 0.0048(15) C9 0.0408(16) 0.062(2) 0.0464(18) -0.0016(16) 0.0100(14) 0.0034(15) C10 0.0493(19) 0.089(3) 0.058(2) -0.016(2) 0.0168(17) 0.008(2) C11 0.0491(19) 0.065(2) 0.064(2) -0.0133(19) 0.0113(17) 0.0024(17) C12 0.0497(19) 0.065(2) 0.0465(19) 0.0163(17) -0.0003(15) -0.0092(16) C13 0.059(2) 0.057(2) 0.0391(17) -0.0002(15) 0.0091(15) -0.0089(17) C14 0.0523(18) 0.053(2) 0.0367(16) 0.0036(14) 0.0037(14) -0.0076(15) C15 0.062(2) 0.069(2) 0.046(2) 0.0084(18) 0.0069(16) 0.0037(19) C16 0.063(2) 0.088(3) 0.045(2) 0.0075(19) 0.0166(17) -0.004(2) N1 0.0385(13) 0.0593(17) 0.0404(14) 0.0006(12) 0.0088(11) 0.0049(12) N2 0.0383(15) 0.079(2) 0.0553(18) -0.0007(16) 0.0142(13) 0.0015(15) O1 0.0441(11) 0.0540(14) 0.0364(11) 0.0059(10) 0.0084(9) -0.0087(10) Cl1A 0.114(5) 0.0638(18) 0.090(5) -0.004(2) 0.050(5) -0.030(2) Cl1B 0.090(3) 0.083(3) 0.092(5) -0.039(3) 0.051(3) -0.043(3) Cl2 0.0599(6) 0.1474(12) 0.0613(6) -0.0115(6) 0.0342(5) 0.0011(6) Cl3 0.0743(6) 0.0694(7) 0.0767(7) 0.0094(5) 0.0223(5) 0.0117(5) S1 0.0757(6) 0.0669(6) 0.0480(5) 0.0149(4) 0.0156(4) -0.0077(5) Br1 0.0712(3) 0.0629(3) 0.0870(3) -0.0164(2) 0.0394(2) -0.0033(2) 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' 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' Cl Cl 0.3639 0.7018 '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' Br Br -0.6763 1.2805 '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 C6 C1 C2 116.2(3) . . ? C6 C1 C7 119.9(3) . . ? C2 C1 C7 123.9(3) . . ? C1 C2 C3 122.8(4) . . ? C1 C2 Cl1A 116.6(4) . . ? C3 C2 Cl1A 118.4(3) . . ? C1 C2 Cl1B 120.1(3) . . ? C3 C2 Cl1B 116.0(3) . . ? Cl1A C2 Cl1B 26.23(17) . . ? C4 C3 C2 118.9(4) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 120.7(3) . . ? C3 C4 Cl2 119.7(3) . . ? C5 C4 Cl2 119.5(3) . . ? C4 C5 C6 119.9(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 121.5(4) . . ? C1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? O1 C7 C1 112.2(3) . . ? O1 C7 C8 105.9(3) . . ? C1 C7 C8 109.6(3) . . ? O1 C7 H7 109.7 . . ? C1 C7 H7 109.7 . . ? C8 C7 H7 109.7 . . ? N1 C8 C7 110.4(3) . . ? N1 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? N1 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? N1 C9 N2 108.0(3) . . ? N1 C9 H9 126.0 . . ? N2 C9 H9 126.0 . . ? C11 C10 N2 107.4(3) . . ? C11 C10 H10 126.3 . . ? N2 C10 H10 126.3 . . ? C10 C11 N1 106.9(4) . . ? C10 C11 H11 126.5 . . ? N1 C11 H11 126.5 . . ? O1 C12 C14 106.9(3) . . ? O1 C12 H12A 110.4 . . ? C14 C12 H12A 110.4 . . ? O1 C12 H12B 110.4 . . ? C14 C12 H12B 110.4 . . ? H12A C12 H12B 108.6 . . ? C14 C13 Cl3 127.5(3) . . ? C14 C13 S1 113.7(3) . . ? Cl3 C13 S1 118.8(2) . . ? C13 C14 C15 110.0(3) . . ? C13 C14 C12 126.4(3) . . ? C15 C14 C12 123.6(3) . . ? C16 C15 C14 114.2(4) . . ? C16 C15 H15 122.9 . . ? C14 C15 H15 122.9 . . ? C15 C16 S1 111.6(3) . . ? C15 C16 H16 124.2 . . ? S1 C16 H16 124.2 . . ? C9 N1 C11 108.6(3) . . ? C9 N1 C8 123.6(3) . . ? C11 N1 C8 127.4(3) . . ? C9 N2 C10 109.1(3) . . ? C9 N2 H2N 122(3) . . ? C10 N2 H2N 129(3) . . ? C7 O1 C12 114.0(2) . . ? Cl1B Cl1A C2 81.3(5) . . ? Cl1A Cl1B C2 72.5(5) . . ? C16 S1 C13 90.4(2) . . ? 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 C1 C6 1.367(6) . ? C1 C2 1.371(5) . ? C1 C7 1.509(4) . ? C2 C3 1.380(5) . ? C2 Cl1A 1.723(6) . ? C2 Cl1B 1.786(5) . ? C3 C4 1.341(6) . ? C3 H3 0.9300 . ? C4 C5 1.348(6) . ? C4 Cl2 1.740(3) . ? C5 C6 1.384(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.421(4) . ? C7 C8 1.521(4) . ? C7 H7 0.9800 . ? C8 N1 1.467(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N1 1.322(4) . ? C9 N2 1.323(4) . ? C9 H9 0.9300 . ? C10 C11 1.334(6) . ? C10 N2 1.359(6) . ? C10 H10 0.9300 . ? C11 N1 1.375(5) . ? C11 H11 0.9300 . ? C12 O1 1.426(4) . ? C12 C14 1.497(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.344(5) . ? C13 Cl3 1.713(4) . ? C13 S1 1.724(4) . ? C14 C15 1.418(5) . ? C15 C16 1.352(6) . ? C15 H15 0.9300 . ? C16 S1 1.704(5) . ? C16 H16 0.9300 . ? N2 H2N 0.83(5) . ? Cl1A Cl1B 0.798(4) . ? 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 C6 C1 C2 C3 -1.1(6) . . . . ? C7 C1 C2 C3 -179.5(4) . . . . ? C6 C1 C2 Cl1A 161.7(7) . . . . ? C7 C1 C2 Cl1A -16.7(8) . . . . ? C6 C1 C2 Cl1B -168.7(7) . . . . ? C7 C1 C2 Cl1B 12.9(8) . . . . ? C1 C2 C3 C4 -0.2(6) . . . . ? Cl1A C2 C3 C4 -162.7(8) . . . . ? Cl1B C2 C3 C4 167.9(7) . . . . ? C2 C3 C4 C5 1.6(7) . . . . ? C2 C3 C4 Cl2 179.9(3) . . . . ? C3 C4 C5 C6 -1.7(8) . . . . ? Cl2 C4 C5 C6 -180.0(5) . . . . ? C2 C1 C6 C5 1.0(8) . . . . ? C7 C1 C6 C5 179.5(5) . . . . ? C4 C5 C6 C1 0.4(9) . . . . ? C6 C1 C7 O1 45.6(5) . . . . ? C2 C1 C7 O1 -136.1(3) . . . . ? C6 C1 C7 C8 -71.8(5) . . . . ? C2 C1 C7 C8 106.6(4) . . . . ? O1 C7 C8 N1 52.6(4) . . . . ? C1 C7 C8 N1 173.9(3) . . . . ? N2 C10 C11 N1 0.3(4) . . . . ? Cl3 C13 C14 C15 -177.1(3) . . . . ? S1 C13 C14 C15 1.4(4) . . . . ? Cl3 C13 C14 C12 2.9(6) . . . . ? S1 C13 C14 C12 -178.6(3) . . . . ? O1 C12 C14 C13 126.7(4) . . . . ? O1 C12 C14 C15 -53.3(5) . . . . ? C13 C14 C15 C16 -1.8(5) . . . . ? C12 C14 C15 C16 178.2(4) . . . . ? C14 C15 C16 S1 1.4(5) . . . . ? N2 C9 N1 C11 0.7(4) . . . . ? N2 C9 N1 C8 174.0(3) . . . . ? C10 C11 N1 C9 -0.6(4) . . . . ? C10 C11 N1 C8 -173.6(3) . . . . ? C7 C8 N1 C9 -96.7(4) . . . . ? C7 C8 N1 C11 75.3(4) . . . . ? N1 C9 N2 C10 -0.5(4) . . . . ? C11 C10 N2 C9 0.1(5) . . . . ? C1 C7 O1 C12 84.2(3) . . . . ? C8 C7 O1 C12 -156.3(3) . . . . ? C14 C12 O1 C7 157.4(3) . . . . ? C1 C2 Cl1A Cl1B 104.8(9) . . . . ? C3 C2 Cl1A Cl1B -91.6(6) . . . . ? C1 C2 Cl1B Cl1A -89.6(10) . . . . ? C3 C2 Cl1B Cl1A 102.1(6) . . . . ? C15 C16 S1 C13 -0.5(3) . . . . ? C14 C13 S1 C16 -0.6(3) . . . . ? Cl3 C13 S1 C16 178.1(2) . . . . ?