#------------------------------------------------------------------------------ #$Date: 2023-11-15 01:36:00 +0200 (Wed, 15 Nov 2023) $ #$Revision: 287595 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247716.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_7247716 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 'C20 H13 Cl3 N2 O1 S, 0.5(C8 H6 O4)' _chemical_formula_sum 'C20 H16 Cl3 N2 O3 S' _chemical_formula_weight 470.76 _chemical_name_common 'Tioconazole-ter-pthalic acid (1:0.5) cocrystal' _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 _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 83.111(3) _cell_angle_beta 83.102(3) _cell_angle_gamma 75.116(3) _cell_formula_units_Z 2 _cell_length_a 7.4880(2) _cell_length_b 11.3843(4) _cell_length_c 13.0280(4) _cell_measurement_reflns_used 13081 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 72.2920 _cell_measurement_theta_min 3.4120 _cell_volume 1060.94(6) _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 0.982 _diffrn_measured_fraction_theta_max 0.960 _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 -130.00 -10.00 1.00 6.00 -- -40.00 -72.00 0.00 120 2 \w -130.00 -10.00 1.00 6.00 -- -40.00 -72.00 70.00 120 3 \w -130.00 -10.00 1.00 6.00 -- -40.00 -72.00 140.00 120 4 \w -130.00 -10.00 1.00 6.00 -- -40.00 -72.00 210.00 120 5 \w -130.00 -10.00 1.00 6.00 -- -40.00 -72.00 280.00 120 6 \w -130.00 50.00 1.00 6.00 -- -40.00 0.00 0.00 180 7 \w -100.00 20.00 1.00 6.00 -- -70.00 72.00 0.00 120 8 \w -100.00 20.00 1.00 6.00 -- -70.00 72.00 70.00 120 9 \w -100.00 20.00 1.00 6.00 -- -70.00 72.00 140.00 120 10 \w -100.00 20.00 1.00 6.00 -- -70.00 72.00 210.00 120 11 \w -100.00 20.00 1.00 6.00 -- -70.00 72.00 280.00 120 12 \w -160.00 20.00 1.00 6.00 -- -70.00 0.00 0.00 180 13 \w -190.00 -70.00 1.00 6.00 -- -100.00 -72.00 0.00 120 14 \w -190.00 -70.00 1.00 6.00 -- -100.00 -72.00 70.00 120 15 \w -190.00 -70.00 1.00 6.00 -- -100.00 -72.00 140.00 120 16 \w -190.00 -70.00 1.00 6.00 -- -100.00 -72.00 210.00 120 17 \w -190.00 -70.00 1.00 6.00 -- -100.00 -72.00 280.00 120 18 \w -130.00 -10.00 1.00 6.00 -- -100.00 72.00 0.00 120 19 \w -130.00 -10.00 1.00 6.00 -- -100.00 72.00 70.00 120 20 \w -130.00 -10.00 1.00 6.00 -- -100.00 72.00 140.00 120 21 \w -130.00 -10.00 1.00 6.00 -- -100.00 72.00 210.00 120 22 \w -130.00 -10.00 1.00 6.00 -- -100.00 72.00 280.00 120 23 \w -190.00 -10.00 1.00 6.00 -- -100.00 0.00 0.00 180 ; _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 CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.1180 _diffrn_reflns_av_unetI/netI 0.0546 _diffrn_reflns_Laue_measured_fraction_full 0.982 _diffrn_reflns_Laue_measured_fraction_max 0.960 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 21968 _diffrn_reflns_point_group_measured_fraction_full 0.982 _diffrn_reflns_point_group_measured_fraction_max 0.960 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.711 _diffrn_reflns_theta_min 3.432 _diffrn_source MicroMax003_Mo _diffrn_source_current 0.6 _diffrn_source_power 0.0 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 5.044 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.49881 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.474 _exptl_crystal_description block _exptl_crystal_F_000 482 _exptl_crystal_size_max 0.380 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.240 _refine_diff_density_max 0.440 _refine_diff_density_min -0.588 _refine_diff_density_rms 0.109 _refine_ls_extinction_coef 0.0052(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 265 _refine_ls_number_reflns 4055 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0679 _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^)+(0.1192P)^2^+0.2409P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1792 _refine_ls_wR_factor_ref 0.1925 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3406 _reflns_number_total 4055 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00948c2.cif _cod_data_source_block TCZ-TPTH2 _cod_database_code 7247716 _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 0.250 _shelx_estimated_absorpt_t_max 0.377 _shelx_res_file ; TITL AM20220712a_Cu in P-1 shelx.res created by SHELXL-2018/3 at 09:24:59 on 28-Jul-2022 CELL 1.54184 7.4880 11.3843 13.0280 83.111 83.102 75.116 ZERR 2.00 0.0002 0.0004 0.0004 0.003 0.003 0.003 LATT 1 SFAC C H N O S CL UNIT 40 32 4 6 2 6 MERG 2 OMIT 1 1 0 FMAP 2 PLAN 2 SIZE 0.240 0.250 0.380 ACTA BOND $H CONF L.S. 10 TEMP 20.00 WGHT 0.119200 0.240900 EXTI 0.005230 FVAR 6.61902 C1 1 -0.516456 1.208404 0.354219 11.00000 0.05630 0.05824 = 0.04326 -0.00102 -0.00320 -0.01307 C2 1 -0.666534 1.176459 0.412707 11.00000 0.05664 0.07996 = 0.04835 -0.00615 -0.00244 -0.02089 C3 1 -0.681027 1.163140 0.520313 11.00000 0.07125 0.08872 = 0.05068 -0.00420 0.00556 -0.03213 AFIX 43 H3 2 -0.783925 1.142536 0.558083 11.00000 -1.20000 AFIX 0 C4 1 -0.539669 1.181132 0.569689 11.00000 0.08458 0.07089 = 0.04501 0.00013 -0.00480 -0.02739 C5 1 -0.389206 1.213658 0.515080 11.00000 0.07923 0.08628 = 0.05467 0.00092 -0.01684 -0.03537 AFIX 43 H5 2 -0.294819 1.226083 0.549610 11.00000 -1.20000 AFIX 0 C6 1 -0.379471 1.227773 0.408019 11.00000 0.06187 0.08257 = 0.05040 0.00122 -0.00705 -0.03136 AFIX 43 H6 2 -0.277990 1.250962 0.370925 11.00000 -1.20000 AFIX 0 C7 1 -0.498398 1.222067 0.236166 11.00000 0.05169 0.06139 = 0.04299 -0.00513 -0.00058 -0.01340 AFIX 13 H7 2 -0.558224 1.165730 0.210373 11.00000 -1.20000 AFIX 0 C8 1 -0.587315 1.352277 0.196412 11.00000 0.05975 0.06227 = 0.04227 -0.00679 -0.00399 -0.00603 AFIX 23 H8A 2 -0.710160 1.377249 0.232407 11.00000 -1.20000 H8B 2 -0.514148 1.405485 0.212649 11.00000 -1.20000 AFIX 0 C9 1 -0.760382 1.411968 0.038296 11.00000 0.06184 0.07108 = 0.05248 -0.00252 -0.00987 -0.00751 AFIX 43 H9 2 -0.876856 1.437276 0.073927 11.00000 -1.20000 AFIX 0 C10 1 -0.542951 1.370589 -0.083581 11.00000 0.07872 0.06283 = 0.04550 -0.00424 -0.00370 -0.01227 AFIX 43 H10 2 -0.480189 1.361527 -0.149333 11.00000 -1.20000 AFIX 0 C11 1 -0.462618 1.341545 0.006176 11.00000 0.06056 0.06205 = 0.04834 -0.00391 -0.00142 -0.00513 AFIX 43 H11 2 -0.336924 1.309991 0.013786 11.00000 -1.20000 AFIX 0 C12 1 -0.215343 1.073671 0.202313 11.00000 0.05868 0.05813 = 0.06082 -0.00079 0.00460 -0.00925 AFIX 23 H12A 2 -0.284487 1.027681 0.171649 11.00000 -1.20000 H12B 2 -0.204951 1.042343 0.274514 11.00000 -1.20000 AFIX 0 C13 1 0.102127 0.954123 0.142721 11.00000 0.05708 0.06481 = 0.06103 -0.00388 -0.00079 -0.01155 C14 1 -0.026528 1.060381 0.145617 11.00000 0.05516 0.06112 = 0.04583 -0.00575 -0.00407 -0.01365 C15 1 0.039502 1.155667 0.085727 11.00000 0.06256 0.06307 = 0.06706 -0.00252 0.00185 -0.01797 AFIX 43 H15 2 -0.030409 1.235985 0.078022 11.00000 -1.20000 AFIX 0 C16 1 0.214422 1.117930 0.040949 11.00000 0.06343 0.07520 = 0.06314 -0.00623 0.00434 -0.02548 AFIX 43 H16 2 0.278238 1.169172 -0.000407 11.00000 -1.20000 AFIX 0 C17 1 -0.914513 1.488126 0.590726 11.00000 0.07764 0.06298 = 0.04958 -0.00644 -0.01515 -0.01216 C18 1 -1.091900 1.470450 0.594579 11.00000 0.07978 0.06975 = 0.04924 -0.00691 -0.01010 -0.01459 AFIX 43 H18 2 -1.152881 1.450168 0.658136 11.00000 -1.20000 AFIX 0 C19 1 -1.178401 1.482745 0.504829 11.00000 0.07636 0.07290 = 0.05523 -0.00621 -0.01209 -0.01806 AFIX 43 H19 2 -1.297823 1.471728 0.507850 11.00000 -1.20000 AFIX 0 C20 1 -0.816500 1.476956 0.686275 11.00000 0.08642 0.06651 = 0.05336 -0.00410 -0.01863 -0.01203 N1 3 -0.603133 1.367768 0.084240 11.00000 0.05719 0.05773 = 0.04178 -0.00438 -0.00655 -0.00705 N2 3 -0.729824 1.415248 -0.064046 11.00000 0.07827 0.07358 = 0.04898 -0.00079 -0.01629 -0.01310 O1 4 -0.308768 1.199364 0.195422 11.00000 0.05271 0.05673 = 0.05093 0.00117 0.00325 -0.00802 O2 4 -0.658348 1.485326 0.684332 11.00000 0.10062 0.11301 = 0.06524 0.00508 -0.02843 -0.04404 O3 4 -0.921980 1.457672 0.772934 11.00000 0.08427 0.11955 = 0.04866 -0.00906 -0.01403 -0.00904 AFIX 148 H3A 2 -0.856919 1.449191 0.827074 11.00000 -1.50000 AFIX 0 S1 5 0.303907 0.966311 0.068962 11.00000 0.05687 0.07399 = 0.08225 -0.01008 0.01068 -0.01131 CL1 6 -0.846529 1.153350 0.351138 11.00000 0.06926 0.17948 = 0.07054 -0.01567 -0.00447 -0.05872 CL2 6 -0.553670 1.163376 0.704375 11.00000 0.14362 0.11787 = 0.04340 0.00185 -0.00608 -0.06398 CL3 6 0.077589 0.815621 0.201490 11.00000 0.08073 0.06682 = 0.13623 0.01926 0.02077 -0.00576 HKLF 4 REM AM20220712a_Cu in P-1 REM wR2 = 0.1925, GooF = S = 1.075, Restrained GooF = 1.075 for all data REM R1 = 0.0679 for 3406 Fo > 4sig(Fo) and 0.0758 for all 4055 data REM 265 parameters refined using 0 restraints END WGHT 0.1192 0.2408 REM Highest difference peak 0.440, deepest hole -0.588, 1-sigma level 0.109 Q1 1 -0.4113 1.1929 0.7112 11.00000 0.05 0.44 Q2 1 0.2753 0.8212 0.2158 11.00000 0.05 0.42 ; _shelx_res_checksum 87019 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 C1 C -0.5165(4) 1.2084(2) 0.35422(18) 0.0532(6) Uani 1 1 d . . . . . C2 C -0.6665(4) 1.1765(3) 0.4127(2) 0.0611(6) Uani 1 1 d . . . . . C3 C -0.6810(4) 1.1631(3) 0.5203(2) 0.0691(8) Uani 1 1 d . . . . . H3 H -0.783925 1.142536 0.558083 0.083 Uiso 1 1 calc R U . . . C4 C -0.5397(5) 1.1811(3) 0.5697(2) 0.0659(7) Uani 1 1 d . . . . . C5 C -0.3892(5) 1.2137(3) 0.5151(2) 0.0704(8) Uani 1 1 d . . . . . H5 H -0.294819 1.226083 0.549610 0.084 Uiso 1 1 calc R U . . . C6 C -0.3795(4) 1.2278(3) 0.4080(2) 0.0629(7) Uani 1 1 d . . . . . H6 H -0.277990 1.250962 0.370925 0.075 Uiso 1 1 calc R U . . . C7 C -0.4984(3) 1.2221(2) 0.23617(19) 0.0524(6) Uani 1 1 d . . . . . H7 H -0.558224 1.165730 0.210373 0.063 Uiso 1 1 calc R U . . . C8 C -0.5873(4) 1.3523(2) 0.19641(19) 0.0563(6) Uani 1 1 d . . . . . H8A H -0.710160 1.377249 0.232407 0.068 Uiso 1 1 calc R U . . . H8B H -0.514148 1.405485 0.212649 0.068 Uiso 1 1 calc R U . . . C9 C -0.7604(4) 1.4120(3) 0.0383(2) 0.0633(7) Uani 1 1 d . . . . . H9 H -0.876856 1.437276 0.073927 0.076 Uiso 1 1 calc R U . . . C10 C -0.5430(4) 1.3706(3) -0.0836(2) 0.0635(7) Uani 1 1 d . . . . . H10 H -0.480189 1.361527 -0.149333 0.076 Uiso 1 1 calc R U . . . C11 C -0.4626(4) 1.3415(2) 0.0062(2) 0.0592(6) Uani 1 1 d . . . . . H11 H -0.336924 1.309991 0.013786 0.071 Uiso 1 1 calc R U . . . C12 C -0.2153(4) 1.0737(2) 0.2023(2) 0.0614(7) Uani 1 1 d . . . . . H12A H -0.284487 1.027681 0.171649 0.074 Uiso 1 1 calc R U . . . H12B H -0.204951 1.042343 0.274514 0.074 Uiso 1 1 calc R U . . . C13 C 0.1021(4) 0.9541(3) 0.1427(2) 0.0622(7) Uani 1 1 d . . . . . C14 C -0.0265(4) 1.0604(2) 0.14562(19) 0.0541(6) Uani 1 1 d . . . . . C15 C 0.0395(4) 1.1557(3) 0.0857(2) 0.0647(7) Uani 1 1 d . . . . . H15 H -0.030409 1.235985 0.078022 0.078 Uiso 1 1 calc R U . . . C16 C 0.2144(4) 1.1179(3) 0.0409(2) 0.0666(7) Uani 1 1 d . . . . . H16 H 0.278238 1.169172 -0.000407 0.080 Uiso 1 1 calc R U . . . C17 C -0.9145(4) 1.4881(3) 0.5907(2) 0.0635(7) Uani 1 1 d . . . . . C18 C -1.0919(4) 1.4704(3) 0.5946(2) 0.0665(7) Uani 1 1 d . . . . . H18 H -1.152881 1.450168 0.658136 0.080 Uiso 1 1 calc R U . . . C19 C -1.1784(5) 1.4827(3) 0.5048(2) 0.0677(7) Uani 1 1 d . . . . . H19 H -1.297823 1.471728 0.507850 0.081 Uiso 1 1 calc R U . . . C20 C -0.8165(5) 1.4770(3) 0.6863(2) 0.0691(8) Uani 1 1 d . . . . . N1 N -0.6031(3) 1.36777(19) 0.08424(15) 0.0534(5) Uani 1 1 d . . . . . N2 N -0.7298(4) 1.4152(2) -0.06405(18) 0.0675(6) Uani 1 1 d . . . . . O1 O -0.3088(2) 1.19936(15) 0.19542(13) 0.0557(5) Uani 1 1 d . . . . . O2 O -0.6583(4) 1.4853(3) 0.68433(18) 0.0891(7) Uani 1 1 d . . . . . O3 O -0.9220(4) 1.4577(3) 0.77293(17) 0.0864(7) Uani 1 1 d . . . . . H3A H -0.857(5) 1.449(5) 0.827(3) 0.130 Uiso 1 1 calc R U . . . S1 S 0.30391(10) 0.96631(7) 0.06896(7) 0.0731(3) Uani 1 1 d . . . . . Cl1 Cl -0.84653(12) 1.15335(12) 0.35114(7) 0.1011(4) Uani 1 1 d . . . . . Cl2 Cl -0.55367(17) 1.16338(10) 0.70437(6) 0.0968(4) Uani 1 1 d . . . . . Cl3 Cl 0.07759(13) 0.81562(8) 0.20149(9) 0.1019(4) 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 C1 0.0563(13) 0.0582(13) 0.0433(13) -0.0010(10) -0.0032(10) -0.0131(10) C2 0.0566(14) 0.0800(17) 0.0484(14) -0.0062(12) -0.0024(11) -0.0209(12) C3 0.0713(18) 0.089(2) 0.0507(15) -0.0042(13) 0.0056(13) -0.0321(15) C4 0.0846(19) 0.0709(16) 0.0450(14) 0.0001(11) -0.0048(13) -0.0274(14) C5 0.0792(19) 0.0863(19) 0.0547(16) 0.0009(13) -0.0168(14) -0.0354(16) C6 0.0619(15) 0.0826(18) 0.0504(15) 0.0012(12) -0.0071(12) -0.0314(13) C7 0.0517(13) 0.0614(13) 0.0430(12) -0.0051(10) -0.0006(10) -0.0134(10) C8 0.0598(14) 0.0623(14) 0.0423(12) -0.0068(10) -0.0040(10) -0.0060(11) C9 0.0618(15) 0.0711(16) 0.0525(15) -0.0025(12) -0.0099(12) -0.0075(12) C10 0.0787(18) 0.0628(15) 0.0455(14) -0.0042(11) -0.0037(12) -0.0123(13) C11 0.0606(15) 0.0621(14) 0.0483(14) -0.0039(11) -0.0014(11) -0.0051(11) C12 0.0587(15) 0.0581(14) 0.0608(15) -0.0008(11) 0.0046(12) -0.0093(11) C13 0.0571(14) 0.0648(15) 0.0610(16) -0.0039(11) -0.0008(12) -0.0116(12) C14 0.0552(13) 0.0611(14) 0.0458(13) -0.0058(10) -0.0041(10) -0.0137(11) C15 0.0626(16) 0.0631(15) 0.0671(17) -0.0025(12) 0.0019(13) -0.0180(12) C16 0.0634(16) 0.0752(17) 0.0631(17) -0.0062(13) 0.0043(13) -0.0255(13) C17 0.0776(18) 0.0630(15) 0.0496(15) -0.0064(11) -0.0151(13) -0.0122(13) C18 0.0798(19) 0.0698(16) 0.0492(15) -0.0069(12) -0.0101(13) -0.0146(14) C19 0.0764(18) 0.0729(17) 0.0552(16) -0.0062(12) -0.0121(13) -0.0181(14) C20 0.086(2) 0.0665(16) 0.0534(16) -0.0041(12) -0.0186(15) -0.0120(15) N1 0.0572(12) 0.0577(11) 0.0418(10) -0.0044(8) -0.0065(9) -0.0070(9) N2 0.0783(16) 0.0736(14) 0.0490(13) -0.0008(10) -0.0163(11) -0.0131(12) O1 0.0527(9) 0.0567(9) 0.0509(10) 0.0012(7) 0.0033(7) -0.0080(7) O2 0.1006(18) 0.1130(19) 0.0652(14) 0.0051(12) -0.0284(13) -0.0440(15) O3 0.0843(15) 0.1195(19) 0.0487(12) -0.0091(11) -0.0140(10) -0.0090(13) S1 0.0569(4) 0.0740(5) 0.0823(6) -0.0101(4) 0.0107(4) -0.0113(3) Cl1 0.0693(5) 0.1795(11) 0.0705(6) -0.0157(6) -0.0045(4) -0.0587(6) Cl2 0.1436(9) 0.1179(7) 0.0434(4) 0.0019(4) -0.0061(4) -0.0640(7) Cl3 0.0807(6) 0.0668(5) 0.1362(9) 0.0193(5) 0.0208(5) -0.0058(4) 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' S S 0.3331 0.5567 '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' 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 117.0(2) . . ? C2 C1 C7 122.7(2) . . ? C6 C1 C7 120.3(2) . . ? C1 C2 C3 122.3(3) . . ? C1 C2 Cl1 119.8(2) . . ? C3 C2 Cl1 117.8(2) . . ? C4 C3 C2 118.3(3) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C5 C4 C3 121.4(3) . . ? C5 C4 Cl2 119.5(2) . . ? C3 C4 Cl2 119.1(2) . . ? C4 C5 C6 119.1(3) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C5 C6 C1 121.9(3) . . ? C5 C6 H6 119.0 . . ? C1 C6 H6 119.0 . . ? O1 C7 C8 105.9(2) . . ? O1 C7 C1 111.2(2) . . ? C8 C7 C1 110.1(2) . . ? O1 C7 H7 109.8 . . ? C8 C7 H7 109.8 . . ? C1 C7 H7 109.8 . . ? N1 C8 C7 113.2(2) . . ? N1 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? N1 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.8 . . ? N2 C9 N1 111.7(3) . . ? N2 C9 H9 124.1 . . ? N1 C9 H9 124.1 . . ? C11 C10 N2 110.1(2) . . ? C11 C10 H10 124.9 . . ? N2 C10 H10 124.9 . . ? C10 C11 N1 106.4(2) . . ? C10 C11 H11 126.8 . . ? N1 C11 H11 126.8 . . ? O1 C12 C14 108.4(2) . . ? O1 C12 H12A 110.0 . . ? C14 C12 H12A 110.0 . . ? O1 C12 H12B 110.0 . . ? C14 C12 H12B 110.0 . . ? H12A C12 H12B 108.4 . . ? C14 C13 Cl3 126.2(2) . . ? C14 C13 S1 113.3(2) . . ? Cl3 C13 S1 120.56(17) . . ? C13 C14 C15 110.8(3) . . ? C13 C14 C12 123.7(2) . . ? C15 C14 C12 125.4(2) . . ? C16 C15 C14 113.2(3) . . ? C16 C15 H15 123.4 . . ? C14 C15 H15 123.4 . . ? C15 C16 S1 112.1(2) . . ? C15 C16 H16 123.9 . . ? S1 C16 H16 123.9 . . ? C18 C17 C19 119.9(3) . 2_386 ? C18 C17 C20 122.2(3) . . ? C19 C17 C20 117.9(3) 2_386 . ? C19 C18 C17 120.5(3) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C17 119.6(3) . 2_386 ? C18 C19 H19 120.2 . . ? C17 C19 H19 120.2 2_386 . ? O2 C20 O3 123.9(3) . . ? O2 C20 C17 123.3(3) . . ? O3 C20 C17 112.8(3) . . ? C9 N1 C11 106.6(2) . . ? C9 N1 C8 125.8(2) . . ? C11 N1 C8 127.5(2) . . ? C9 N2 C10 105.2(2) . . ? C12 O1 C7 113.50(19) . . ? C20 O3 H3A 109.5 . . ? C16 S1 C13 90.59(14) . . ? 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 1.383(4) . ? C1 C6 1.385(4) . ? C1 C7 1.520(3) . ? C2 C3 1.386(4) . ? C2 Cl1 1.738(3) . ? C3 C4 1.372(4) . ? C3 H3 0.9300 . ? C4 C5 1.368(4) . ? C4 Cl2 1.736(3) . ? C5 C6 1.380(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.424(3) . ? C7 C8 1.517(4) . ? C7 H7 0.9800 . ? C8 N1 1.466(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.323(4) . ? C9 N1 1.338(3) . ? C9 H9 0.9300 . ? C10 C11 1.346(4) . ? C10 N2 1.364(4) . ? C10 H10 0.9300 . ? C11 N1 1.373(3) . ? C11 H11 0.9300 . ? C12 O1 1.420(3) . ? C12 C14 1.494(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.340(4) . ? C13 Cl3 1.712(3) . ? C13 S1 1.718(3) . ? C14 C15 1.418(4) . ? C15 C16 1.352(4) . ? C15 H15 0.9300 . ? C16 S1 1.696(3) . ? C16 H16 0.9300 . ? C17 C18 1.388(4) . ? C17 C19 1.398(4) 2_386 ? C17 C20 1.496(4) . ? C18 C19 1.379(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 O2 1.209(4) . ? C20 O3 1.327(4) . ? O3 H3A 0.89(5) . ? 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 -0.5(4) . . . . ? C7 C1 C2 C3 179.4(3) . . . . ? C6 C1 C2 Cl1 178.8(2) . . . . ? C7 C1 C2 Cl1 -1.3(4) . . . . ? C1 C2 C3 C4 -0.8(5) . . . . ? Cl1 C2 C3 C4 180.0(2) . . . . ? C2 C3 C4 C5 1.2(5) . . . . ? C2 C3 C4 Cl2 -179.3(2) . . . . ? C3 C4 C5 C6 -0.4(5) . . . . ? Cl2 C4 C5 C6 -179.9(2) . . . . ? C4 C5 C6 C1 -0.9(5) . . . . ? C2 C1 C6 C5 1.3(4) . . . . ? C7 C1 C6 C5 -178.6(3) . . . . ? C2 C1 C7 O1 -153.1(2) . . . . ? C6 C1 C7 O1 26.8(3) . . . . ? C2 C1 C7 C8 89.8(3) . . . . ? C6 C1 C7 C8 -90.4(3) . . . . ? O1 C7 C8 N1 69.3(3) . . . . ? C1 C7 C8 N1 -170.4(2) . . . . ? N2 C10 C11 N1 0.5(3) . . . . ? Cl3 C13 C14 C15 -178.2(2) . . . . ? S1 C13 C14 C15 0.2(3) . . . . ? Cl3 C13 C14 C12 0.1(4) . . . . ? S1 C13 C14 C12 178.5(2) . . . . ? O1 C12 C14 C13 175.6(3) . . . . ? O1 C12 C14 C15 -6.3(4) . . . . ? C13 C14 C15 C16 -0.4(4) . . . . ? C12 C14 C15 C16 -178.7(3) . . . . ? C14 C15 C16 S1 0.4(4) . . . . ? C19 C17 C18 C19 -0.7(5) 2_386 . . . ? C20 C17 C18 C19 179.4(3) . . . . ? C17 C18 C19 C17 0.7(5) . . . 2_386 ? C18 C17 C20 O2 175.8(3) . . . . ? C19 C17 C20 O2 -4.1(5) 2_386 . . . ? C18 C17 C20 O3 -4.6(4) . . . . ? C19 C17 C20 O3 175.5(3) 2_386 . . . ? N2 C9 N1 C11 0.3(3) . . . . ? N2 C9 N1 C8 179.8(2) . . . . ? C10 C11 N1 C9 -0.5(3) . . . . ? C10 C11 N1 C8 -179.9(2) . . . . ? C7 C8 N1 C9 122.9(3) . . . . ? C7 C8 N1 C11 -57.7(4) . . . . ? N1 C9 N2 C10 0.0(3) . . . . ? C11 C10 N2 C9 -0.3(3) . . . . ? C14 C12 O1 C7 173.0(2) . . . . ? C8 C7 O1 C12 -164.8(2) . . . . ? C1 C7 O1 C12 75.5(3) . . . . ? C15 C16 S1 C13 -0.3(3) . . . . ? C14 C13 S1 C16 0.0(3) . . . . ? Cl3 C13 S1 C16 178.6(2) . . . . ?