#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:01:35 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288801 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247713.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_7247713 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, 0.5(C2 H2 O4), 0.5(C2 O4)' _chemical_formula_sum 'C18 H15 Cl3 N2 O5 S' _chemical_formula_weight 477.73 _chemical_name_common 'Tioconazole-oxalate-oxalic acid (1:0.5:0.5)salt 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 mixed _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 112.364(4) _cell_angle_beta 105.711(2) _cell_angle_gamma 96.357(2) _cell_formula_units_Z 2 _cell_length_a 10.2522(2) _cell_length_b 10.7638(4) _cell_length_c 11.0528(4) _cell_measurement_reflns_used 12802 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 72.4630 _cell_measurement_theta_min 4.5780 _cell_volume 1054.06(7) _computing_cell_refinement 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_data_collection 'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)' _computing_data_reduction 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _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 0.983 _diffrn_measured_fraction_theta_max 0.962 _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 0.1141 _diffrn_reflns_av_unetI/netI 0.0550 _diffrn_reflns_Laue_measured_fraction_full 0.983 _diffrn_reflns_Laue_measured_fraction_max 0.962 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 21579 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.962 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.756 _diffrn_reflns_theta_min 4.576 _diffrn_source MicroMax003_Cu _diffrn_source_current 0.6 _diffrn_source_power 0.0 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 5.158 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.19346 _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 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.570 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.930 _refine_diff_density_min -0.669 _refine_diff_density_rms 0.119 _refine_ls_extinction_coef 0.023(3) _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 1.041 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 271 _refine_ls_number_reflns 4031 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0990 _refine_ls_R_factor_gt 0.0918 _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^)+(0.1552P)^2^+1.3541P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2553 _refine_ls_wR_factor_ref 0.2641 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3495 _reflns_number_total 4031 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00948c2.cif _cod_data_source_block TCZ-OXAC _cod_depositor_comments 'Adding full bibliography for 7247709--7247724.cif.' _cod_database_code 7247713 _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 0.157 _shelx_estimated_absorpt_t_max 0.577 _shelx_res_file ; TITL SD20220125b_Cu in P-1 shelx.res created by SHELXL-2018/3 at 18:35:50 on 28-Jul-2022 CELL 1.54184 10.2522 10.7638 11.0528 112.364 105.711 96.357 ZERR 2.00 0.0002 0.0004 0.0004 0.004 0.002 0.002 LATT 1 SFAC C H N O S CL UNIT 36 30 4 10 2 6 MERG 2 FMAP 2 PLAN 5 SIZE 0.120 0.250 0.570 ACTA BOND $H CONF L.S. 10 TEMP 20.00 WGHT 0.155200 1.354100 EXTI 0.023081 FVAR 6.08668 C1 1 0.102973 0.215765 0.702156 11.00000 0.03635 0.04947 = 0.05029 0.02289 0.00719 0.00781 C2 1 0.001030 0.178141 0.575227 11.00000 0.04609 0.05289 = 0.06274 0.02571 0.00282 0.00614 C3 1 -0.140714 0.141029 0.555084 11.00000 0.04071 0.05950 = 0.08825 0.02756 -0.01089 0.00368 AFIX 43 H3 2 -0.208455 0.118657 0.469776 11.00000 -1.20000 AFIX 0 C4 1 -0.176993 0.138581 0.665060 11.00000 0.04097 0.07306 = 0.09547 0.03783 0.01726 0.00840 C5 1 -0.080951 0.174144 0.791782 11.00000 0.04810 0.06445 = 0.08904 0.03435 0.02908 0.00847 AFIX 43 H5 2 -0.108005 0.172368 0.865028 11.00000 -1.20000 AFIX 0 C6 1 0.060042 0.213588 0.809126 11.00000 0.04138 0.05786 = 0.05967 0.02506 0.01547 0.00731 AFIX 43 H6 2 0.126891 0.239161 0.895780 11.00000 -1.20000 AFIX 0 C7 1 0.257482 0.257992 0.725522 11.00000 0.03057 0.05823 = 0.04117 0.02605 0.00735 0.00943 AFIX 13 H7 2 0.278931 0.191200 0.648513 11.00000 -1.20000 AFIX 0 C8 1 0.299316 0.402092 0.734245 11.00000 0.02666 0.06201 = 0.04752 0.03136 0.01408 0.01417 AFIX 23 H8A 2 0.231685 0.411811 0.659829 11.00000 -1.20000 H8B 2 0.299945 0.470885 0.822182 11.00000 -1.20000 AFIX 0 C9 1 0.559998 0.464119 0.822420 11.00000 0.03092 0.08378 = 0.04210 0.03088 0.00914 0.01232 AFIX 43 H9 2 0.572798 0.487505 0.915671 11.00000 -1.20000 AFIX 0 C10 1 0.602579 0.425190 0.632363 11.00000 0.04377 0.12341 = 0.05666 0.04996 0.02678 0.02106 AFIX 43 H10 2 0.649913 0.416458 0.569799 11.00000 -1.20000 AFIX 0 C11 1 0.463971 0.400829 0.602182 11.00000 0.03738 0.12555 = 0.04308 0.04922 0.01297 0.01593 AFIX 43 H11 2 0.397393 0.372290 0.514728 11.00000 -1.20000 AFIX 0 C12 1 0.360620 0.131631 0.848695 11.00000 0.04854 0.05684 = 0.05811 0.02867 0.00995 0.01422 AFIX 23 H12A 2 0.408265 0.089720 0.784337 11.00000 -1.20000 H12B 2 0.270470 0.069659 0.819360 11.00000 -1.20000 AFIX 0 C13 1 0.396245 0.144172 1.090088 11.00000 0.07684 0.08319 = 0.07762 0.05447 0.02744 0.02667 C14 1 0.445136 0.159061 0.992643 11.00000 0.05531 0.05299 = 0.05751 0.03090 0.01085 0.01561 C15 1 0.591588 0.214600 1.050780 11.00000 0.05774 0.06737 = 0.07426 0.03953 0.00669 0.00999 AFIX 43 H15 2 0.645470 0.232738 1.001208 11.00000 -1.20000 AFIX 0 C16 1 0.644648 0.238408 1.185780 11.00000 0.07962 0.06715 = 0.07944 0.03144 -0.01492 0.00719 AFIX 43 H16 2 0.738936 0.274486 1.238628 11.00000 -1.20000 AFIX 0 C17 1 0.961386 0.500665 0.551619 11.00000 0.02814 0.07110 = 0.03676 0.03471 0.01235 0.01554 C18 1 1.033439 0.520737 0.952849 11.00000 0.03231 0.06352 = 0.02726 0.02384 0.00996 0.01171 N1 3 0.438221 0.425423 0.722755 11.00000 0.02484 0.06269 = 0.03976 0.02985 0.00932 0.01161 N2 3 0.660593 0.464594 0.769815 11.00000 0.02743 0.07885 = 0.06103 0.03797 0.01298 0.01364 O1 4 0.343797 0.263687 0.852555 11.00000 0.03496 0.05525 = 0.04578 0.02901 0.00698 0.00994 O2 4 0.836709 0.462863 0.511682 11.00000 0.02998 0.14128 = 0.04613 0.04900 0.01403 0.00773 O3 4 1.045701 0.544558 0.676612 11.00000 0.03195 0.10674 = 0.03874 0.04519 0.01365 0.01577 O4 4 0.944628 0.529650 0.851481 11.00000 0.03090 0.09617 = 0.03926 0.04400 0.01216 0.01765 O5 4 1.159250 0.543027 0.980188 11.00000 0.02977 0.09110 = 0.04099 0.03690 0.01231 0.01425 S2 5 0.522779 0.196143 1.248591 11.00000 0.12624 0.09912 = 0.05866 0.04468 0.02036 0.04503 CL1 6 0.044979 0.175355 0.433099 11.00000 0.08932 0.07484 = 0.04940 0.02921 0.00648 0.01540 CL2 6 -0.352947 0.086238 0.638614 11.00000 0.03905 0.13413 = 0.18940 0.07139 0.02568 0.00031 CL3 6 0.225553 0.079874 1.065902 11.00000 0.08638 0.22190 = 0.19651 0.16431 0.07354 0.05590 H2N 2 0.753872 0.471865 0.818070 11.00000 0.12301 H3O 2 1.000667 0.534372 0.721074 11.00000 0.10811 HKLF 4 REM SD20220125b_Cu in P-1 REM wR2 = 0.2641, GooF = S = 1.041, Restrained GooF = 1.041 for all data REM R1 = 0.0918 for 3495 Fo > 4sig(Fo) and 0.0990 for all 4031 data REM 271 parameters refined using 0 restraints END WGHT 0.1555 1.3487 REM Highest difference peak 0.930, deepest hole -0.669, 1-sigma level 0.119 Q1 1 -0.2079 0.1839 0.7894 11.00000 0.05 0.93 Q2 1 -0.0212 0.2111 0.4987 11.00000 0.05 0.90 Q3 1 -0.3433 0.0765 0.5453 11.00000 0.05 0.74 Q4 1 0.2145 0.1623 1.1763 11.00000 0.05 0.52 Q5 1 0.4361 0.1741 1.2117 11.00000 0.05 0.48 ; _shelx_res_checksum 48752 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 0.1030(4) 0.2158(4) 0.7022(4) 0.0468(8) Uani 1 1 d . . . . . C2 C 0.0010(4) 0.1781(4) 0.5752(5) 0.0576(10) Uani 1 1 d . . . . . C3 C -0.1407(5) 0.1410(5) 0.5551(6) 0.0722(15) Uani 1 1 d . . . . . H3 H -0.208455 0.118657 0.469776 0.087 Uiso 1 1 calc R U . . . C4 C -0.1770(5) 0.1386(5) 0.6651(6) 0.0711(13) Uani 1 1 d . . . . . C5 C -0.0810(5) 0.1741(5) 0.7918(6) 0.0659(12) Uani 1 1 d . . . . . H5 H -0.108005 0.172368 0.865028 0.079 Uiso 1 1 calc R U . . . C6 C 0.0600(4) 0.2136(4) 0.8091(5) 0.0538(10) Uani 1 1 d . . . . . H6 H 0.126891 0.239161 0.895780 0.065 Uiso 1 1 calc R U . . . C7 C 0.2575(3) 0.2580(4) 0.7255(4) 0.0430(8) Uani 1 1 d . . . . . H7 H 0.278931 0.191200 0.648513 0.052 Uiso 1 1 calc R U . . . C8 C 0.2993(3) 0.4021(4) 0.7342(4) 0.0422(8) Uani 1 1 d . . . . . H8A H 0.231685 0.411811 0.659829 0.051 Uiso 1 1 calc R U . . . H8B H 0.299945 0.470885 0.822182 0.051 Uiso 1 1 calc R U . . . C9 C 0.5600(4) 0.4641(5) 0.8224(4) 0.0519(9) Uani 1 1 d . . . . . H9 H 0.572798 0.487505 0.915671 0.062 Uiso 1 1 calc R U . . . C10 C 0.6026(5) 0.4252(6) 0.6324(5) 0.0687(13) Uani 1 1 d . . . . . H10 H 0.649913 0.416458 0.569799 0.082 Uiso 1 1 calc R U . . . C11 C 0.4640(4) 0.4008(6) 0.6022(5) 0.0649(13) Uani 1 1 d . . . . . H11 H 0.397393 0.372290 0.514728 0.078 Uiso 1 1 calc R U . . . C12 C 0.3606(4) 0.1316(4) 0.8487(5) 0.0549(10) Uani 1 1 d . . . . . H12A H 0.408265 0.089720 0.784337 0.066 Uiso 1 1 calc R U . . . H12B H 0.270470 0.069659 0.819360 0.066 Uiso 1 1 calc R U . . . C13 C 0.3962(6) 0.1442(6) 1.0901(6) 0.0718(13) Uani 1 1 d . . . . . C14 C 0.4451(5) 0.1591(4) 0.9926(5) 0.0546(10) Uani 1 1 d . . . . . C15 C 0.5916(5) 0.2146(5) 1.0508(6) 0.0674(12) Uani 1 1 d . . . . . H15 H 0.645470 0.232738 1.001208 0.081 Uiso 1 1 calc R U . . . C16 C 0.6446(6) 0.2384(6) 1.1858(6) 0.0857(18) Uani 1 1 d . . . . . H16 H 0.738936 0.274486 1.238628 0.103 Uiso 1 1 calc R U . . . C17 C 0.9614(3) 0.5007(4) 0.5516(4) 0.0410(8) Uani 1 1 d . . . . . C18 C 1.0334(3) 0.5207(4) 0.9528(3) 0.0396(8) Uani 1 1 d . . . . . N1 N 0.4382(3) 0.4254(3) 0.7228(3) 0.0402(7) Uani 1 1 d . . . . . N2 N 0.6606(3) 0.4646(4) 0.7698(4) 0.0536(9) Uani 1 1 d . . . . . O1 O 0.3438(2) 0.2637(3) 0.8526(3) 0.0445(6) Uani 1 1 d . . . . . O2 O 0.8367(3) 0.4629(4) 0.5117(3) 0.0705(10) Uani 1 1 d . . . . . O3 O 1.0457(3) 0.5446(4) 0.6766(3) 0.0543(8) Uani 1 1 d . . . . . O4 O 0.9446(2) 0.5296(3) 0.8515(3) 0.0503(7) Uani 1 1 d . . . . . O5 O 1.1593(2) 0.5430(3) 0.9802(3) 0.0511(7) Uani 1 1 d . . . . . S2 S 0.5228(2) 0.19614(18) 1.24859(15) 0.0920(6) Uani 1 1 d . . . . . Cl1 Cl 0.04498(15) 0.17535(13) 0.43310(12) 0.0745(5) Uani 1 1 d . . . . . Cl2 Cl -0.35295(14) 0.0862(2) 0.6386(3) 0.1249(8) Uani 1 1 d . . . . . Cl3 Cl 0.2256(2) 0.0799(3) 1.0659(3) 0.1367(10) Uani 1 1 d . . . . . H2N H 0.754(8) 0.472(8) 0.818(9) 0.12(3) Uiso 1 1 d . . . . . H3O H 1.001(8) 0.534(8) 0.721(8) 0.11(2) 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 0.0364(18) 0.0495(19) 0.050(2) 0.0229(17) 0.0072(16) 0.0078(14) C2 0.046(2) 0.053(2) 0.063(3) 0.0257(19) 0.0028(19) 0.0061(17) C3 0.041(2) 0.059(3) 0.088(4) 0.028(2) -0.011(2) 0.0037(18) C4 0.041(2) 0.073(3) 0.095(4) 0.038(3) 0.017(2) 0.0084(19) C5 0.048(2) 0.064(3) 0.089(4) 0.034(2) 0.029(2) 0.0085(19) C6 0.041(2) 0.058(2) 0.060(2) 0.0251(19) 0.0155(18) 0.0073(16) C7 0.0306(16) 0.058(2) 0.0412(19) 0.0261(16) 0.0074(14) 0.0094(14) C8 0.0267(15) 0.062(2) 0.048(2) 0.0314(17) 0.0141(14) 0.0142(14) C9 0.0309(17) 0.084(3) 0.042(2) 0.0309(19) 0.0091(15) 0.0123(17) C10 0.044(2) 0.123(4) 0.057(3) 0.050(3) 0.027(2) 0.021(2) C11 0.037(2) 0.126(4) 0.043(2) 0.049(3) 0.0130(17) 0.016(2) C12 0.049(2) 0.057(2) 0.058(2) 0.0287(19) 0.0100(18) 0.0142(17) C13 0.077(3) 0.083(3) 0.078(3) 0.054(3) 0.027(3) 0.027(3) C14 0.055(2) 0.053(2) 0.058(2) 0.0309(19) 0.0109(19) 0.0156(17) C15 0.058(3) 0.067(3) 0.074(3) 0.040(2) 0.007(2) 0.010(2) C16 0.080(4) 0.067(3) 0.079(4) 0.031(3) -0.015(3) 0.007(3) C17 0.0281(15) 0.071(2) 0.0368(18) 0.0347(17) 0.0123(14) 0.0155(14) C18 0.0323(16) 0.064(2) 0.0273(16) 0.0238(15) 0.0100(13) 0.0117(14) N1 0.0248(13) 0.0627(18) 0.0398(16) 0.0298(14) 0.0093(11) 0.0116(12) N2 0.0274(15) 0.079(2) 0.061(2) 0.0380(18) 0.0130(14) 0.0136(14) O1 0.0350(12) 0.0552(14) 0.0458(14) 0.0290(12) 0.0070(10) 0.0099(10) O2 0.0300(13) 0.141(3) 0.0461(16) 0.0490(19) 0.0140(12) 0.0077(15) O3 0.0320(12) 0.107(2) 0.0387(14) 0.0452(15) 0.0136(11) 0.0158(13) O4 0.0309(12) 0.096(2) 0.0393(14) 0.0440(14) 0.0122(10) 0.0177(12) O5 0.0298(12) 0.091(2) 0.0410(14) 0.0369(14) 0.0123(10) 0.0142(12) S2 0.1262(14) 0.0991(11) 0.0587(9) 0.0447(8) 0.0204(8) 0.0450(10) Cl1 0.0893(9) 0.0748(8) 0.0494(7) 0.0292(6) 0.0065(6) 0.0154(6) Cl2 0.0390(7) 0.1341(15) 0.189(2) 0.0714(15) 0.0257(9) 0.0003(7) Cl3 0.0864(11) 0.222(3) 0.197(2) 0.164(2) 0.0735(14) 0.0559(14) 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 C6 C1 C2 117.4(4) . . ? C6 C1 C7 120.3(3) . . ? C2 C1 C7 122.3(4) . . ? C1 C2 C3 121.9(5) . . ? C1 C2 Cl1 120.9(3) . . ? C3 C2 Cl1 117.2(4) . . ? C4 C3 C2 117.9(5) . . ? C4 C3 H3 121.0 . . ? C2 C3 H3 121.0 . . ? C5 C4 C3 122.5(4) . . ? C5 C4 Cl2 119.4(4) . . ? C3 C4 Cl2 118.1(4) . . ? C4 C5 C6 118.1(5) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C1 C6 C5 122.1(4) . . ? C1 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? O1 C7 C1 112.5(3) . . ? O1 C7 C8 105.1(3) . . ? C1 C7 C8 112.2(3) . . ? O1 C7 H7 109.0 . . ? C1 C7 H7 109.0 . . ? C8 C7 H7 109.0 . . ? N1 C8 C7 110.3(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 . . ? N2 C9 N1 109.6(3) . . ? N2 C9 H9 125.2 . . ? N1 C9 H9 125.2 . . ? C11 C10 N2 107.3(4) . . ? C11 C10 H10 126.3 . . ? N2 C10 H10 126.3 . . ? C10 C11 N1 107.6(4) . . ? C10 C11 H11 126.2 . . ? N1 C11 H11 126.2 . . ? O1 C12 C14 106.1(3) . . ? O1 C12 H12A 110.5 . . ? C14 C12 H12A 110.5 . . ? O1 C12 H12B 110.5 . . ? C14 C12 H12B 110.5 . . ? H12A C12 H12B 108.7 . . ? C14 C13 S2 113.8(4) . . ? C14 C13 Cl3 126.0(4) . . ? S2 C13 Cl3 120.1(3) . . ? C13 C14 C15 109.8(4) . . ? C13 C14 C12 126.6(4) . . ? C15 C14 C12 123.5(4) . . ? C16 C15 C14 112.9(5) . . ? C16 C15 H15 123.5 . . ? C14 C15 H15 123.5 . . ? C15 C16 S2 113.2(4) . . ? C15 C16 H16 123.4 . . ? S2 C16 H16 123.4 . . ? O2 C17 O3 127.1(3) . . ? O2 C17 C17 120.6(4) . 2_766 ? O3 C17 C17 112.3(3) . 2_766 ? O5 C18 O4 126.3(3) . . ? O5 C18 C18 120.0(4) . 2_767 ? O4 C18 C18 113.7(3) . 2_767 ? C9 N1 C11 107.2(3) . . ? C9 N1 C8 127.5(3) . . ? C11 N1 C8 125.2(3) . . ? C9 N2 C10 108.4(3) . . ? C9 N2 H2N 124(5) . . ? C10 N2 H2N 127(5) . . ? C7 O1 C12 114.6(3) . . ? C17 O3 H3O 107(5) . . ? C16 S2 C13 90.2(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 C1 C6 1.376(6) . ? C1 C2 1.380(6) . ? C1 C7 1.521(5) . ? C2 C3 1.396(6) . ? C2 Cl1 1.738(5) . ? C3 C4 1.372(8) . ? C3 H3 0.9300 . ? C4 C5 1.356(8) . ? C4 Cl2 1.738(5) . ? C5 C6 1.399(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.417(4) . ? C7 C8 1.522(5) . ? C7 H7 0.9800 . ? C8 N1 1.466(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.314(5) . ? C9 N1 1.318(5) . ? C9 H9 0.9300 . ? C10 C11 1.339(6) . ? C10 N2 1.344(6) . ? C10 H10 0.9300 . ? C11 N1 1.361(5) . ? C11 H11 0.9300 . ? C12 O1 1.437(5) . ? C12 C14 1.486(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.358(7) . ? C13 S2 1.711(6) . ? C13 Cl3 1.718(6) . ? C14 C15 1.418(6) . ? C15 C16 1.352(8) . ? C15 H15 0.9300 . ? C16 S2 1.684(8) . ? C16 H16 0.9300 . ? C17 O2 1.199(4) . ? C17 O3 1.283(4) . ? C17 C17 1.552(6) 2_766 ? C18 O5 1.216(4) . ? C18 O4 1.281(4) . ? C18 C18 1.559(6) 2_767 ? N2 H2N 0.94(8) . ? O3 H3O 0.79(8) . ? 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 0.9(6) . . . . ? C7 C1 C2 C3 -179.3(4) . . . . ? C6 C1 C2 Cl1 -179.1(3) . . . . ? C7 C1 C2 Cl1 0.7(6) . . . . ? C1 C2 C3 C4 -2.0(7) . . . . ? Cl1 C2 C3 C4 178.0(4) . . . . ? C2 C3 C4 C5 1.8(8) . . . . ? C2 C3 C4 Cl2 -177.7(4) . . . . ? C3 C4 C5 C6 -0.5(7) . . . . ? Cl2 C4 C5 C6 178.9(4) . . . . ? C2 C1 C6 C5 0.4(6) . . . . ? C7 C1 C6 C5 -179.4(4) . . . . ? C4 C5 C6 C1 -0.7(7) . . . . ? C6 C1 C7 O1 12.4(5) . . . . ? C2 C1 C7 O1 -167.4(3) . . . . ? C6 C1 C7 C8 -105.9(4) . . . . ? C2 C1 C7 C8 74.3(5) . . . . ? O1 C7 C8 N1 71.1(3) . . . . ? C1 C7 C8 N1 -166.3(3) . . . . ? N2 C10 C11 N1 -0.2(6) . . . . ? S2 C13 C14 C15 0.2(5) . . . . ? Cl3 C13 C14 C15 -179.6(4) . . . . ? S2 C13 C14 C12 -175.9(3) . . . . ? Cl3 C13 C14 C12 4.2(8) . . . . ? O1 C12 C14 C13 98.4(5) . . . . ? O1 C12 C14 C15 -77.2(5) . . . . ? C13 C14 C15 C16 -0.1(6) . . . . ? C12 C14 C15 C16 176.2(4) . . . . ? C14 C15 C16 S2 -0.1(6) . . . . ? N2 C9 N1 C11 -0.1(5) . . . . ? N2 C9 N1 C8 175.6(3) . . . . ? C10 C11 N1 C9 0.2(6) . . . . ? C10 C11 N1 C8 -175.7(4) . . . . ? C7 C8 N1 C9 -82.5(5) . . . . ? C7 C8 N1 C11 92.6(5) . . . . ? N1 C9 N2 C10 0.0(5) . . . . ? C11 C10 N2 C9 0.1(6) . . . . ? C1 C7 O1 C12 79.4(4) . . . . ? C8 C7 O1 C12 -158.2(3) . . . . ? C14 C12 O1 C7 -176.1(3) . . . . ? C15 C16 S2 C13 0.2(4) . . . . ? C14 C13 S2 C16 -0.3(4) . . . . ? Cl3 C13 S2 C16 179.6(4) . . . . ?