#------------------------------------------------------------------------------ #$Date: 2023-11-15 01:36:00 +0200 (Wed, 15 Nov 2023) $ #$Revision: 287595 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247715.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_7247715 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 Multi-component Crystals of the Antifungal Drug Tioconazole and the Assessment of their Biopharmaceutical Attributes ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00948C _journal_year 2023 _chemical_formula_moiety 'C16 H14 Cl3 N2 O S, H O4 S' _chemical_formula_sum 'C16 H15 Cl3 N2 O5 S2' _chemical_formula_weight 485.77 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-I 2ya' _space_group_name_H-M_alt 'I 1 2/a 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary direct _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2023-07-31 deposited with the CCDC. 2023-11-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.406(5) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 16.9432(10) _cell_length_b 6.7811(3) _cell_length_c 34.455(2) _cell_measurement_reflns_used 5705 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 31.0520 _cell_measurement_theta_min 2.8640 _cell_volume 3916.1(4) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_molecular_graphics 'Ortep for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX publication routines (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS-2013/1 (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector CCD _diffrn_detector_area_resol_mean 28.5714 _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.881 _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (4x4 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support Loop _diffrn_radiation_monochromator Confocal _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1256 _diffrn_reflns_av_unetI/netI 0.1014 _diffrn_reflns_Laue_measured_fraction_full 0.979 _diffrn_reflns_Laue_measured_fraction_max 0.881 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_number 20473 _diffrn_reflns_point_group_measured_fraction_full 0.979 _diffrn_reflns_point_group_measured_fraction_max 0.881 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.497 _diffrn_reflns_theta_min 2.390 _diffrn_source MicroMax003_Mo _diffrn_source_current 0.6 _diffrn_source_power 0.0 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 0.714 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.01338 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1984 _exptl_crystal_size_max 0.340 _exptl_crystal_size_mid 0.230 _exptl_crystal_size_min 0.110 _refine_diff_density_max 1.036 _refine_diff_density_min -1.230 _refine_diff_density_rms 0.204 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 258 _refine_ls_number_reflns 5730 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.1484 _refine_ls_R_factor_gt 0.1013 _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^)+(0.1837P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2524 _refine_ls_wR_factor_ref 0.3134 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3352 _reflns_number_total 5730 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00948c2.cif _cod_data_source_block TCZ-SULF _cod_original_sg_symbol_H-M 'I 2/a' _cod_database_code 7247715 _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_min 0.793 _shelx_estimated_absorpt_t_max 0.926 _shelx_res_file ; TITL SD20181027F_Mo in I2/a shelx.res created by SHELXL-2018/3 at 10:46:57 on 26-Jul-2022 CELL 0.71073 16.9432 6.7811 34.4546 90.000 98.406 90.000 ZERR 8.00 0.0010 0.0003 0.0020 0.000 0.005 0.000 LATT 2 SYMM 1/2 - X, Y, - Z SFAC C H N O S CL UNIT 128 120 16 40 16 24 MERG 2 FMAP 2 PLAN 5 SIZE 0.110 0.230 0.340 ACTA BOND $H CONF L.S. 10 TEMP 20.00 WGHT 0.183700 FVAR 0.51657 C1 1 0.084963 -0.108514 0.087002 11.00000 0.01538 0.02694 = 0.02988 -0.00041 0.00053 -0.00336 C2 1 0.050153 -0.252689 0.061602 11.00000 0.01829 0.03410 = 0.04522 -0.00106 -0.00224 -0.00242 C3 1 -0.021441 -0.224022 0.037116 11.00000 0.01683 0.03408 = 0.03995 -0.00490 -0.00307 -0.00390 AFIX 43 H3 2 -0.043298 -0.322839 0.020141 11.00000 -1.20000 AFIX 0 C4 1 -0.059194 -0.045417 0.038641 11.00000 0.01210 0.03790 = 0.02827 0.00126 -0.00149 -0.00172 C5 1 -0.026887 0.104605 0.063561 11.00000 0.02665 0.03929 = 0.03400 -0.00572 -0.00626 0.00428 AFIX 43 H5 2 -0.052510 0.225780 0.063825 11.00000 -1.20000 AFIX 0 C6 1 0.044375 0.069797 0.088028 11.00000 0.02596 0.03469 = 0.03456 -0.00669 0.00251 -0.00152 AFIX 43 H6 2 0.065484 0.167470 0.105470 11.00000 -1.20000 AFIX 0 C7 1 0.162005 -0.141302 0.114889 11.00000 0.01748 0.03034 = 0.02565 -0.00060 -0.00306 -0.00515 AFIX 13 H7 2 0.193788 -0.242137 0.103903 11.00000 -1.20000 AFIX 0 C8 1 0.142862 -0.211756 0.154423 11.00000 0.01428 0.03284 = 0.03591 0.00476 -0.00420 0.00063 AFIX 23 H8A 2 0.113599 -0.109308 0.165862 11.00000 -1.20000 H8B 2 0.108815 -0.327169 0.150455 11.00000 -1.20000 AFIX 0 C9 1 0.243938 -0.441410 0.187828 11.00000 0.02099 0.03217 = 0.03384 0.00448 -0.00159 0.00069 AFIX 43 H9 2 0.221470 -0.557246 0.176760 11.00000 -1.20000 AFIX 0 C10 1 0.325731 -0.234142 0.222258 11.00000 0.02190 0.04199 = 0.03107 -0.00095 0.00065 -0.00365 AFIX 43 H10 2 0.369220 -0.184820 0.239050 11.00000 -1.20000 AFIX 0 C11 1 0.264960 -0.128699 0.202856 11.00000 0.02825 0.02985 = 0.03787 0.00062 0.00421 -0.00531 AFIX 43 H11 2 0.258649 0.007400 0.203689 11.00000 -1.20000 AFIX 0 C12 1 0.256224 0.079494 0.092594 11.00000 0.02396 0.03457 = 0.02744 -0.00363 0.00004 -0.00190 AFIX 23 H12A 2 0.223816 0.143255 0.070604 11.00000 -1.20000 H12B 2 0.278783 -0.039787 0.083214 11.00000 -1.20000 AFIX 0 C13 1 0.339270 0.394822 0.096666 11.00000 0.02559 0.03326 = 0.02588 -0.00491 -0.00728 0.00083 C14 1 0.322017 0.216329 0.110530 11.00000 0.01927 0.03041 = 0.02699 -0.00130 0.00377 0.00034 C15 1 0.373603 0.169778 0.145492 11.00000 0.02307 0.03372 = 0.04007 0.00515 -0.00124 -0.01069 AFIX 43 H15 2 0.370732 0.052373 0.159167 11.00000 -1.20000 AFIX 0 C16 1 0.427572 0.313521 0.157017 11.00000 0.02268 0.04116 = 0.02700 -0.00183 -0.00593 -0.00368 AFIX 43 H16 2 0.465559 0.305751 0.179363 11.00000 -1.20000 AFIX 0 N1 3 0.213912 -0.260580 0.181544 11.00000 0.01744 0.03356 = 0.03024 0.00455 0.00236 0.00300 N2 3 0.311153 -0.427533 0.212507 11.00000 0.02190 0.03794 = 0.03862 0.00314 -0.00550 0.00782 O1 4 0.208598 0.032711 0.122412 11.00000 0.01896 0.02839 = 0.02897 -0.00076 -0.00077 -0.00585 O2 4 0.023646 0.078038 0.206319 11.00000 0.04726 0.03631 = 0.05014 -0.01012 0.01416 -0.01425 AFIX 147 H2 2 0.017320 0.022460 0.226776 11.00000 -1.50000 AFIX 0 O3 4 0.081940 0.349523 0.178560 11.00000 0.03107 0.05193 = 0.04120 0.01060 -0.00531 -0.01053 O4 4 0.131606 0.255233 0.245471 11.00000 0.02400 0.04603 = 0.05051 0.01278 -0.00986 0.00541 O5 4 0.002229 0.404062 0.230301 11.00000 0.03921 0.04495 = 0.05297 -0.00911 -0.00631 0.01763 S1 5 0.417774 0.511137 0.125700 11.00000 0.02550 0.03299 = 0.03613 -0.00269 -0.00032 -0.00599 S2 5 0.063334 0.284506 0.216007 11.00000 0.01856 0.02788 = 0.03484 -0.00031 -0.00394 0.00182 CL1 6 0.096792 -0.479513 0.059142 11.00000 0.03447 0.03214 = 0.09961 -0.02012 -0.02250 0.00302 CL2 6 -0.148715 -0.005783 0.007907 11.00000 0.02063 0.05470 = 0.03089 -0.00061 -0.00683 0.00006 CL3 6 0.298240 0.507381 0.053474 11.00000 0.03223 0.03721 = 0.03971 0.00688 -0.00517 -0.00155 H2N 2 0.330837 -0.529160 0.222787 11.00000 0.03397 HKLF 4 REM SD20181027F_Mo in I2/a REM wR2 = 0.3134, GooF = S = 1.038, Restrained GooF = 1.038 for all data REM R1 = 0.1013 for 3352 Fo > 4sig(Fo) and 0.1484 for all 5730 data REM 258 parameters refined using 0 restraints END WGHT 0.1836 0.0000 REM Highest difference peak 1.036, deepest hole -1.230, 1-sigma level 0.204 Q1 1 0.4314 0.3745 0.1081 11.00000 0.05 0.97 Q2 1 0.4302 0.6427 0.1084 11.00000 0.05 0.92 Q3 1 -0.1626 0.1368 0.0229 11.00000 0.05 0.90 Q4 1 -0.1400 0.1400 -0.0092 11.00000 0.05 0.89 Q5 1 0.2901 0.6365 0.0738 11.00000 0.05 0.88 ; _shelx_res_checksum 91960 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' '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 C1 C 0.0850(3) -0.1085(6) 0.08700(12) 0.0243(8) Uani 1 1 d . . . . . C2 C 0.0502(3) -0.2527(7) 0.06160(14) 0.0332(10) Uani 1 1 d . . . . . C3 C -0.0214(3) -0.2240(6) 0.03712(13) 0.0310(10) Uani 1 1 d . . . . . H3 H -0.043298 -0.322839 0.020141 0.037 Uiso 1 1 calc R U . . . C4 C -0.0592(3) -0.0454(7) 0.03864(12) 0.0265(9) Uani 1 1 d . . . . . C5 C -0.0269(3) 0.1046(7) 0.06356(13) 0.0344(11) Uani 1 1 d . . . . . H5 H -0.052510 0.225780 0.063825 0.041 Uiso 1 1 calc R U . . . C6 C 0.0444(3) 0.0698(7) 0.08803(13) 0.0319(10) Uani 1 1 d . . . . . H6 H 0.065484 0.167470 0.105470 0.038 Uiso 1 1 calc R U . . . C7 C 0.1620(3) -0.1413(6) 0.11489(11) 0.0251(8) Uani 1 1 d . . . . . H7 H 0.193788 -0.242137 0.103903 0.030 Uiso 1 1 calc R U . . . C8 C 0.1429(3) -0.2118(6) 0.15442(12) 0.0285(9) Uani 1 1 d . . . . . H8A H 0.113599 -0.109308 0.165862 0.034 Uiso 1 1 calc R U . . . H8B H 0.108815 -0.327169 0.150455 0.034 Uiso 1 1 calc R U . . . C9 C 0.2439(3) -0.4414(7) 0.18783(13) 0.0296(9) Uani 1 1 d . . . . . H9 H 0.221470 -0.557246 0.176760 0.035 Uiso 1 1 calc R U . . . C10 C 0.3257(3) -0.2341(7) 0.22226(13) 0.0320(10) Uani 1 1 d . . . . . H10 H 0.369220 -0.184820 0.239050 0.038 Uiso 1 1 calc R U . . . C11 C 0.2650(3) -0.1287(7) 0.20286(13) 0.0321(10) Uani 1 1 d . . . . . H11 H 0.258649 0.007400 0.203689 0.038 Uiso 1 1 calc R U . . . C12 C 0.2562(3) 0.0795(7) 0.09259(12) 0.0290(9) Uani 1 1 d . . . . . H12A H 0.223816 0.143255 0.070604 0.035 Uiso 1 1 calc R U . . . H12B H 0.278783 -0.039787 0.083214 0.035 Uiso 1 1 calc R U . . . C13 C 0.3393(3) 0.3948(6) 0.09667(12) 0.0293(9) Uani 1 1 d . . . . . C14 C 0.3220(3) 0.2163(6) 0.11053(12) 0.0255(9) Uani 1 1 d . . . . . C15 C 0.3736(3) 0.1698(7) 0.14549(13) 0.0329(10) Uani 1 1 d . . . . . H15 H 0.370732 0.052373 0.159167 0.039 Uiso 1 1 calc R U . . . C16 C 0.4276(3) 0.3135(7) 0.15702(12) 0.0312(10) Uani 1 1 d . . . . . H16 H 0.465559 0.305751 0.179363 0.037 Uiso 1 1 calc R U . . . N1 N 0.2139(2) -0.2606(5) 0.18154(10) 0.0272(8) Uani 1 1 d . . . . . N2 N 0.3112(3) -0.4275(6) 0.21251(12) 0.0338(9) Uani 1 1 d . . . . . O1 O 0.20860(19) 0.0327(4) 0.12241(9) 0.0259(7) Uani 1 1 d . . . . . O2 O 0.0236(3) 0.0780(5) 0.20632(11) 0.0439(9) Uani 1 1 d . . . . . H2 H 0.017320 0.022460 0.226776 0.066 Uiso 1 1 calc R U . . . O3 O 0.0819(2) 0.3495(5) 0.17856(10) 0.0425(9) Uani 1 1 d . . . . . O4 O 0.1316(2) 0.2552(5) 0.24547(10) 0.0417(9) Uani 1 1 d . . . . . O5 O 0.0022(2) 0.4041(5) 0.23030(11) 0.0470(10) Uani 1 1 d . . . . . S1 S 0.41777(8) 0.51114(16) 0.12570(3) 0.0320(3) Uani 1 1 d . . . . . S2 S 0.06333(7) 0.28451(16) 0.21601(3) 0.0279(3) Uani 1 1 d . . . . . Cl1 Cl 0.09679(9) -0.47951(19) 0.05914(5) 0.0586(5) Uani 1 1 d . . . . . Cl2 Cl -0.14871(7) -0.00578(18) 0.00791(3) 0.0365(3) Uani 1 1 d . . . . . Cl3 Cl 0.29824(8) 0.50738(17) 0.05347(4) 0.0374(3) Uani 1 1 d . . . . . H2N H 0.331(3) -0.529(7) 0.2228(14) 0.034(15) 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 0.015(2) 0.0269(19) 0.030(2) -0.0004(15) 0.0005(16) -0.0034(15) C2 0.018(2) 0.034(2) 0.045(3) -0.0011(19) -0.0022(18) -0.0024(18) C3 0.017(2) 0.034(2) 0.040(2) -0.0049(17) -0.0031(18) -0.0039(17) C4 0.012(2) 0.038(2) 0.028(2) 0.0013(16) -0.0015(16) -0.0017(16) C5 0.027(3) 0.039(3) 0.034(2) -0.0057(18) -0.0063(19) 0.0043(19) C6 0.026(3) 0.035(2) 0.035(2) -0.0067(18) 0.0025(19) -0.0015(18) C7 0.017(2) 0.030(2) 0.026(2) -0.0006(15) -0.0031(16) -0.0051(16) C8 0.014(2) 0.033(2) 0.036(2) 0.0048(17) -0.0042(16) 0.0006(16) C9 0.021(2) 0.032(2) 0.034(2) 0.0045(17) -0.0016(18) 0.0007(17) C10 0.022(2) 0.042(2) 0.031(2) -0.0009(18) 0.0007(17) -0.0037(19) C11 0.028(3) 0.030(2) 0.038(2) 0.0006(17) 0.0042(19) -0.0053(18) C12 0.024(3) 0.035(2) 0.027(2) -0.0036(16) 0.0000(17) -0.0019(17) C13 0.026(3) 0.033(2) 0.026(2) -0.0049(16) -0.0073(17) 0.0008(17) C14 0.019(2) 0.030(2) 0.027(2) -0.0013(15) 0.0038(16) 0.0003(16) C15 0.023(3) 0.034(2) 0.040(3) 0.0051(18) -0.0012(19) -0.0107(18) C16 0.023(3) 0.041(2) 0.027(2) -0.0018(17) -0.0059(17) -0.0037(18) N1 0.017(2) 0.0336(18) 0.0302(18) 0.0046(14) 0.0024(14) 0.0030(15) N2 0.022(2) 0.038(2) 0.039(2) 0.0031(17) -0.0055(16) 0.0078(17) O1 0.0190(17) 0.0284(14) 0.0290(15) -0.0008(11) -0.0008(12) -0.0059(12) O2 0.047(3) 0.0363(19) 0.050(2) -0.0101(15) 0.0142(18) -0.0143(17) O3 0.031(2) 0.052(2) 0.0412(19) 0.0106(16) -0.0053(15) -0.0105(17) O4 0.024(2) 0.046(2) 0.051(2) 0.0128(16) -0.0099(15) 0.0054(15) O5 0.039(2) 0.045(2) 0.053(2) -0.0091(16) -0.0063(18) 0.0176(17) S1 0.0255(7) 0.0330(6) 0.0361(7) -0.0027(4) -0.0003(5) -0.0060(4) S2 0.0186(6) 0.0279(5) 0.0348(6) -0.0003(4) -0.0039(4) 0.0018(4) Cl1 0.0345(9) 0.0321(6) 0.0996(13) -0.0201(7) -0.0225(8) 0.0030(5) Cl2 0.0206(7) 0.0547(8) 0.0309(6) -0.0006(4) -0.0068(5) 0.0001(5) Cl3 0.0322(8) 0.0372(6) 0.0397(7) 0.0069(4) -0.0052(5) -0.0016(5) 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' 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' Cl Cl 0.1484 0.1585 '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 C2 C1 C6 117.5(4) . . ? C2 C1 C7 122.9(4) . . ? C6 C1 C7 119.5(4) . . ? C1 C2 C3 122.6(4) . . ? C1 C2 Cl1 120.1(4) . . ? C3 C2 Cl1 117.3(3) . . ? C4 C3 C2 118.1(4) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C3 C4 C5 121.7(4) . . ? C3 C4 Cl2 118.8(3) . . ? C5 C4 Cl2 119.5(4) . . ? C6 C5 C4 118.7(4) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C1 121.4(4) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? O1 C7 C1 113.4(3) . . ? O1 C7 C8 106.4(3) . . ? C1 C7 C8 109.6(3) . . ? O1 C7 H7 109.1 . . ? C1 C7 H7 109.1 . . ? C8 C7 H7 109.1 . . ? N1 C8 C7 112.5(4) . . ? N1 C8 H8A 109.1 . . ? C7 C8 H8A 109.1 . . ? N1 C8 H8B 109.1 . . ? C7 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? N2 C9 N1 108.2(4) . . ? N2 C9 H9 125.9 . . ? N1 C9 H9 125.9 . . ? C11 C10 N2 106.8(4) . . ? C11 C10 H10 126.6 . . ? N2 C10 H10 126.6 . . ? C10 C11 N1 107.1(4) . . ? C10 C11 H11 126.4 . . ? N1 C11 H11 126.4 . . ? O1 C12 C14 107.6(3) . . ? O1 C12 H12A 110.2 . . ? C14 C12 H12A 110.2 . . ? O1 C12 H12B 110.2 . . ? C14 C12 H12B 110.2 . . ? H12A C12 H12B 108.5 . . ? C14 C13 Cl3 128.4(3) . . ? C14 C13 S1 113.1(3) . . ? Cl3 C13 S1 118.4(3) . . ? C13 C14 C15 111.2(4) . . ? C13 C14 C12 126.2(4) . . ? C15 C14 C12 122.5(4) . . ? C16 C15 C14 113.3(4) . . ? C16 C15 H15 123.4 . . ? C14 C15 H15 123.4 . . ? C15 C16 S1 112.3(3) . . ? C15 C16 H16 123.9 . . ? S1 C16 H16 123.9 . . ? C9 N1 C11 108.4(4) . . ? C9 N1 C8 125.2(4) . . ? C11 N1 C8 126.3(4) . . ? C9 N2 C10 109.5(4) . . ? C9 N2 H2N 118(4) . . ? C10 N2 H2N 131(4) . . ? C7 O1 C12 114.1(3) . . ? S2 O2 H2 109.5 . . ? C16 S1 C13 90.2(2) . . ? O4 S2 O3 114.6(2) . . ? O4 S2 O5 112.1(2) . . ? O3 S2 O5 113.1(2) . . ? O4 S2 O2 107.6(2) . . ? O3 S2 O2 103.0(2) . . ? O5 S2 O2 105.4(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 C2 1.385(6) . ? C1 C6 1.394(6) . ? C1 C7 1.520(6) . ? C2 C3 1.386(6) . ? C2 Cl1 1.737(5) . ? C3 C4 1.374(6) . ? C3 H3 0.9300 . ? C4 C5 1.391(6) . ? C4 Cl2 1.739(4) . ? C5 C6 1.388(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.422(5) . ? C7 C8 1.523(6) . ? C7 H7 0.9800 . ? C8 N1 1.450(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.321(6) . ? C9 N1 1.333(5) . ? C9 H9 0.9300 . ? C10 C11 1.348(6) . ? C10 N2 1.367(6) . ? C10 H10 0.9300 . ? C11 N1 1.379(5) . ? C11 H11 0.9300 . ? C12 O1 1.432(5) . ? C12 C14 1.511(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.349(6) . ? C13 Cl3 1.726(4) . ? C13 S1 1.733(4) . ? C14 C15 1.417(6) . ? C15 C16 1.356(6) . ? C15 H15 0.9300 . ? C16 S1 1.713(5) . ? C16 H16 0.9300 . ? N2 H2N 0.82(5) . ? O2 S2 1.568(3) . ? O2 H2 0.8200 . ? O3 S2 1.441(3) . ? O4 S2 1.437(3) . ? O5 S2 1.456(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 1.4(7) . . . . ? C7 C1 C2 C3 177.9(4) . . . . ? C6 C1 C2 Cl1 -179.3(4) . . . . ? C7 C1 C2 Cl1 -2.8(6) . . . . ? C1 C2 C3 C4 -0.6(7) . . . . ? Cl1 C2 C3 C4 -180.0(4) . . . . ? C2 C3 C4 C5 0.7(7) . . . . ? C2 C3 C4 Cl2 179.5(4) . . . . ? C3 C4 C5 C6 -1.5(7) . . . . ? Cl2 C4 C5 C6 179.6(4) . . . . ? C4 C5 C6 C1 2.3(7) . . . . ? C2 C1 C6 C5 -2.2(7) . . . . ? C7 C1 C6 C5 -178.9(4) . . . . ? C2 C1 C7 O1 148.8(4) . . . . ? C6 C1 C7 O1 -34.8(5) . . . . ? C2 C1 C7 C8 -92.5(5) . . . . ? C6 C1 C7 C8 84.0(5) . . . . ? O1 C7 C8 N1 -61.5(4) . . . . ? C1 C7 C8 N1 175.5(3) . . . . ? N2 C10 C11 N1 0.2(5) . . . . ? Cl3 C13 C14 C15 174.9(4) . . . . ? S1 C13 C14 C15 -0.4(5) . . . . ? Cl3 C13 C14 C12 -5.9(7) . . . . ? S1 C13 C14 C12 178.8(4) . . . . ? O1 C12 C14 C13 -125.7(5) . . . . ? O1 C12 C14 C15 53.4(6) . . . . ? C13 C14 C15 C16 0.3(6) . . . . ? C12 C14 C15 C16 -178.9(4) . . . . ? C14 C15 C16 S1 -0.1(6) . . . . ? N2 C9 N1 C11 0.7(5) . . . . ? N2 C9 N1 C8 176.2(4) . . . . ? C10 C11 N1 C9 -0.5(5) . . . . ? C10 C11 N1 C8 -176.0(4) . . . . ? C7 C8 N1 C9 -96.6(5) . . . . ? C7 C8 N1 C11 78.2(5) . . . . ? N1 C9 N2 C10 -0.6(5) . . . . ? C11 C10 N2 C9 0.2(5) . . . . ? C1 C7 O1 C12 -81.3(4) . . . . ? C8 C7 O1 C12 158.1(4) . . . . ? C14 C12 O1 C7 -159.9(3) . . . . ? C15 C16 S1 C13 -0.1(4) . . . . ? C14 C13 S1 C16 0.3(4) . . . . ? Cl3 C13 S1 C16 -175.5(3) . . . . ?