#------------------------------------------------------------------------------ #$Date: 2023-11-15 01:36:00 +0200 (Wed, 15 Nov 2023) $ #$Revision: 287595 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247724.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_7247724 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 H11 Cl3 N2 O S, C16 H13 Cl3 N2 O S, C8 H6 O4' _chemical_formula_sum 'C40 H30 Cl6 N4 O6 S2' _chemical_formula_weight 939.50 _chemical_name_common 'Tioconazole-Terepthalic acid 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 _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 78.507(2) _cell_angle_beta 83.668(2) _cell_angle_gamma 85.091(2) _cell_formula_units_Z 2 _cell_length_a 10.7290(3) _cell_length_b 12.8274(3) _cell_length_c 16.0617(5) _cell_measurement_reflns_used 14208 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 72.0590 _cell_measurement_theta_min 2.7680 _cell_volume 2148.36(10) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _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 0.959 _diffrn_measurement_details ; scan: Number of images: 120 Slice: -130.0000 - -10.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -72.0000 Phi: 0.0000 XTD: 35.0004 2theta: -39.6388 scan: Number of images: 120 Slice: -130.0000 - -10.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -72.0000 Phi: 70.0000 XTD: 35.0004 2theta: -39.6388 scan: Number of images: 120 Slice: -130.0000 - -10.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -72.0000 Phi: 140.0000 XTD: 35.0004 2theta: -39.6388 scan: Number of images: 120 Slice: -130.0000 - -10.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -72.0000 Phi: 210.0000 XTD: 35.0004 2theta: -39.6388 scan: Number of images: 120 Slice: -130.0000 - -10.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -72.0000 Phi: 280.0000 XTD: 35.0004 2theta: -39.6388 scan: Number of images: 180 Slice: -130.0000 - 50.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 0.0000 Phi: 0.0000 XTD: 35.0004 2theta: -39.6388 scan: Number of images: 120 Slice: -100.0000 - 20.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 72.0000 Phi: 0.0000 XTD: 35.0004 2theta: -69.6388 scan: Number of images: 120 Slice: -100.0000 - 20.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 72.0000 Phi: 70.0000 XTD: 35.0004 2theta: -69.6388 scan: Number of images: 120 Slice: -100.0000 - 20.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 72.0000 Phi: 140.0000 XTD: 35.0004 2theta: -69.6388 scan: Number of images: 120 Slice: -100.0000 - 20.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 72.0000 Phi: 210.0000 XTD: 35.0004 2theta: -69.6388 scan: Number of images: 120 Slice: -100.0000 - 20.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 72.0000 Phi: 280.0000 XTD: 35.0004 2theta: -69.6388 scan: Number of images: 180 Slice: -160.0000 - 20.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 0.0000 Phi: 0.0000 XTD: 35.0004 2theta: -69.6388 scan: Number of images: 120 Slice: -190.0000 - -70.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -72.0000 Phi: 0.0000 XTD: 35.0004 2theta: -99.6388 scan: Number of images: 120 Slice: -190.0000 - -70.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -72.0000 Phi: 70.0000 XTD: 35.0004 2theta: -99.6388 scan: Number of images: 120 Slice: -190.0000 - -70.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -72.0000 Phi: 140.0000 XTD: 35.0004 2theta: -99.6388 scan: Number of images: 120 Slice: -190.0000 - -70.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -72.0000 Phi: 210.0000 XTD: 35.0004 2theta: -99.6388 scan: Number of images: 120 Slice: -190.0000 - -70.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -72.0000 Phi: 280.0000 XTD: 35.0004 2theta: -99.6388 scan: Number of images: 120 Slice: -130.0000 - -10.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 72.0000 Phi: 0.0000 XTD: 35.0004 2theta: -99.6388 scan: Number of images: 120 Slice: -130.0000 - -10.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 72.0000 Phi: 70.0000 XTD: 35.0004 2theta: -99.6388 scan: Number of images: 120 Slice: -130.0000 - -10.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 72.0000 Phi: 140.0000 XTD: 35.0004 2theta: -99.6388 scan: Number of images: 120 Slice: -130.0000 - -10.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 72.0000 Phi: 210.0000 XTD: 35.0004 2theta: -99.6388 scan: Number of images: 120 Slice: -130.0000 - -10.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 72.0000 Phi: 280.0000 XTD: 35.0004 2theta: -99.6388 scan: Number of images: 180 Slice: -190.0000 - -10.0000 Image width: 1.0000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 0.0000 Phi: 0.0000 XTD: 35.0004 2theta: -99.6388 ; _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 0.1375 _diffrn_reflns_av_unetI/netI 0.0717 _diffrn_reflns_Laue_measured_fraction_full 0.982 _diffrn_reflns_Laue_measured_fraction_max 0.959 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 45274 _diffrn_reflns_point_group_measured_fraction_full 0.982 _diffrn_reflns_point_group_measured_fraction_max 0.959 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.864 _diffrn_reflns_theta_min 2.820 _diffrn_source MicroMax003_Cu _diffrn_source_current 0.6 _diffrn_source_power 0.0 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 4.982 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.23093 _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 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 960 _exptl_crystal_size_max 0.380 _exptl_crystal_size_mid 0.340 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.724 _refine_diff_density_min -0.501 _refine_diff_density_rms 0.097 _refine_ls_extinction_coef 0.0065(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 1.187 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 543 _refine_ls_number_reflns 8208 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.187 _refine_ls_R_factor_all 0.1246 _refine_ls_R_factor_gt 0.0958 _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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2802 _refine_ls_wR_factor_ref 0.3330 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5232 _reflns_number_total 8208 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00948c2.cif _cod_data_source_block TCA-TPTH1 _cod_database_code 7247724 _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 0.253 _shelx_estimated_absorpt_t_max 0.610 _shelx_res_file ; TITL SD20200318j_Cu in P-1 shelx.res created by SHELXL-2018/3 at 12:34:51 on 26-Jul-2022 CELL 1.54184 10.7290 12.8274 16.0617 78.507 83.668 85.091 ZERR 2.00 0.0003 0.0003 0.0005 0.002 0.002 0.002 LATT 1 SFAC C H N O S CL UNIT 80 60 8 12 4 12 MERG 2 OMIT 0 1 1 OMIT 0 -1 1 OMIT 0 0 3 OMIT -2 2 0 OMIT -3 0 1 OMIT 0 0 5 FMAP 2 PLAN 5 SIZE 0.110 0.340 0.380 ACTA BOND $H CONF L.S. 10 TEMP 20.00 WGHT 0.200000 EXTI 0.006521 FVAR 3.55576 0.49998 PART 2 C15A 1 -0.140115 0.922919 0.366701 21.00000 0.11514 C16A 1 -0.068679 0.938392 0.414154 21.00000 0.13418 S1A 5 0.019609 0.824823 0.480497 21.00000 0.14968 0.26797 = 0.10206 -0.07027 -0.00911 -0.03988 CL3B 6 -0.040603 0.622461 0.492881 21.00000 0.25530 0.10999 = 0.13816 -0.02661 -0.04084 0.06995 PART 1 C15B 1 -0.204428 0.906437 0.383355 -21.00000 0.11070 C16B 1 -0.145764 0.951956 0.413385 -21.00000 0.12676 S1B 5 -0.014240 0.864093 0.475306 -21.00000 0.14023 0.16452 = 0.11974 -0.05628 -0.01176 -0.04417 CL3A 6 0.002970 0.638176 0.482038 -21.00000 0.20456 0.30687 = 0.22425 -0.09463 -0.08713 0.12551 PART 0 C1 1 -0.105068 0.565484 0.254106 11.00000 0.07979 0.07238 = 0.07147 -0.02271 0.00216 -0.00816 C2 1 0.002689 0.501035 0.268329 11.00000 0.09252 0.07104 = 0.09140 -0.02425 0.00596 -0.00335 C3 1 0.006235 0.390296 0.274919 11.00000 0.12383 0.08068 = 0.09909 -0.02415 0.00398 0.00317 AFIX 43 H3 2 0.081070 0.348868 0.282577 11.00000 -1.20000 AFIX 0 C4 1 -0.098801 0.345678 0.270054 11.00000 0.15768 0.08303 = 0.07829 -0.01743 -0.00212 -0.02224 C5 1 -0.211476 0.406614 0.255569 11.00000 0.13496 0.10635 = 0.10753 -0.02465 -0.01761 -0.04288 AFIX 43 H5 2 -0.284164 0.374120 0.251373 11.00000 -1.20000 AFIX 0 C6 1 -0.212952 0.515548 0.247628 11.00000 0.10656 0.09757 = 0.10465 -0.01817 -0.02789 -0.02152 AFIX 43 H6 2 -0.287474 0.556643 0.237738 11.00000 -1.20000 AFIX 0 C7 1 -0.106123 0.685443 0.244585 11.00000 0.06829 0.07946 = 0.06964 -0.02315 0.00142 -0.00080 AFIX 13 H7 2 -0.039848 0.703086 0.275841 11.00000 -1.20000 AFIX 0 C8 1 -0.082713 0.736478 0.150490 11.00000 0.08461 0.07689 = 0.07052 -0.02412 0.00263 -0.00323 AFIX 23 H8A 2 -0.018045 0.693699 0.123026 11.00000 -1.20000 H8B 2 -0.159054 0.737732 0.122992 11.00000 -1.20000 AFIX 0 C9 1 -0.109776 0.935823 0.112050 11.00000 0.06978 0.07657 = 0.08607 -0.02128 -0.00991 0.00801 AFIX 43 H9 2 -0.190675 0.939167 0.095584 11.00000 -1.20000 AFIX 0 C10 1 0.063423 0.980498 0.139334 11.00000 0.07324 0.08206 = 0.13361 -0.00778 -0.01725 -0.00646 AFIX 43 H10 2 0.127611 1.021656 0.145937 11.00000 -1.20000 AFIX 0 C11 1 0.068025 0.874647 0.156389 11.00000 0.06929 0.08106 = 0.16143 -0.00162 -0.02562 -0.00127 AFIX 43 H11 2 0.135341 0.829467 0.176264 11.00000 -1.20000 AFIX 0 C12 1 -0.243187 0.714351 0.366018 11.00000 0.09361 0.10802 = 0.07958 -0.03429 0.01234 -0.00866 AFIX 23 H12A 2 -0.225016 0.639577 0.389593 11.00000 -1.20000 H12B 2 -0.330524 0.732699 0.383228 11.00000 -1.20000 AFIX 0 C13 1 -0.070976 0.755550 0.447973 11.00000 0.11711 0.17526 = 0.09621 -0.05065 0.00561 0.01435 C14 1 -0.160709 0.780576 0.400758 11.00000 0.11420 0.14892 = 0.07241 -0.03516 0.01014 -0.00046 C17 1 0.398666 0.070680 0.263803 11.00000 0.07343 0.08160 = 0.07371 -0.01676 -0.00386 -0.00990 C18 1 0.503735 0.006115 0.244385 11.00000 0.07517 0.08067 = 0.07961 -0.01412 -0.00935 -0.00235 C19 1 0.503196 -0.103338 0.254138 11.00000 0.10522 0.07689 = 0.09010 -0.01278 -0.01701 0.00143 AFIX 43 H19 2 0.575505 -0.144127 0.240165 11.00000 -1.20000 AFIX 0 C20 1 0.395157 -0.149004 0.284389 11.00000 0.13008 0.09020 = 0.08242 -0.01076 -0.02099 -0.01977 C21 1 0.286393 -0.089314 0.303717 11.00000 0.11744 0.12277 = 0.10480 -0.01134 -0.00794 -0.05621 AFIX 43 H21 2 0.212071 -0.122298 0.323670 11.00000 -1.20000 AFIX 0 C22 1 0.289404 0.021071 0.292939 11.00000 0.07086 0.11916 = 0.11258 -0.02536 0.00675 -0.02133 AFIX 43 H22 2 0.216345 0.061689 0.305669 11.00000 -1.20000 AFIX 0 CL6 6 0.568981 0.120820 0.483893 11.00000 0.28851 0.14378 = 0.21155 0.01995 -0.07043 0.03452 C24 1 0.394518 0.242386 0.158530 11.00000 0.07784 0.07691 = 0.08046 -0.02001 -0.00870 -0.00711 AFIX 23 H24A 2 0.442378 0.197804 0.122539 11.00000 -1.20000 H24B 2 0.307247 0.246135 0.146935 11.00000 -1.20000 AFIX 0 C27 1 0.560401 0.372183 0.109993 11.00000 0.08420 0.07326 = 0.10506 -0.01568 -0.00128 0.00271 AFIX 43 H27 2 0.627641 0.324644 0.098731 11.00000 -1.20000 AFIX 0 N4 3 0.446023 0.521983 0.122856 11.00000 0.09277 0.07253 = 0.09131 -0.02024 -0.00393 0.00246 C25 1 0.376305 0.440863 0.142647 11.00000 0.08148 0.08269 = 0.09837 -0.02545 -0.00072 0.00814 AFIX 43 H25 2 0.290597 0.447138 0.159234 11.00000 -1.20000 AFIX 0 C28 1 0.323449 0.221916 0.388069 11.00000 0.12548 0.14343 = 0.08296 -0.03937 0.02566 -0.01675 AFIX 23 H28A 2 0.344677 0.146724 0.408164 11.00000 -1.20000 H28B 2 0.244809 0.240886 0.419166 11.00000 -1.20000 AFIX 0 C29 1 0.525681 0.247835 0.446666 11.00000 0.18563 0.11896 = 0.08623 -0.01762 -0.00567 0.00570 C30 1 0.425059 0.285966 0.406426 11.00000 0.13960 0.11446 = 0.07008 -0.03381 0.00904 0.01867 C31 1 0.423007 0.404324 0.383894 11.00000 0.16387 0.12402 = 0.14702 -0.04131 -0.03769 0.02232 AFIX 43 H31 2 0.360099 0.446600 0.355456 11.00000 -1.20000 AFIX 0 C32 1 0.516811 0.441670 0.407759 11.00000 0.23718 0.13083 = 0.17838 -0.06150 -0.03897 -0.00872 AFIX 43 H32 2 0.529357 0.514105 0.398109 11.00000 -1.20000 AFIX 0 C33 1 0.004701 0.389979 0.028643 11.00000 0.06076 0.07185 = 0.06611 -0.01664 -0.00046 0.00224 C34 1 -0.107718 0.446433 0.011441 11.00000 0.06043 0.07452 = 0.11240 -0.01327 -0.00213 -0.00032 AFIX 43 H34 2 -0.181247 0.410785 0.018888 11.00000 -1.20000 AFIX 0 C35 1 0.111923 0.445639 0.016463 11.00000 0.06297 0.07525 = 0.11660 -0.01189 -0.00652 0.00627 AFIX 43 H35 2 0.188687 0.408841 0.027501 11.00000 -1.20000 AFIX 0 C36 1 0.015469 0.272710 0.060005 11.00000 0.06568 0.07970 = 0.07812 -0.01656 -0.00111 0.00501 C37 1 0.506989 0.890557 0.030892 11.00000 0.07635 0.07228 = 0.06887 -0.02255 -0.01247 0.00733 C38 1 0.392789 0.950574 0.038790 11.00000 0.07303 0.07863 = 0.08561 -0.02520 -0.00504 0.00326 AFIX 43 H38 2 0.320964 0.917279 0.064790 11.00000 -1.20000 AFIX 0 C39 1 0.613609 0.941265 -0.008208 11.00000 0.07057 0.07551 = 0.08855 -0.02719 -0.00989 0.00494 AFIX 43 H39 2 0.689845 0.901737 -0.013724 11.00000 -1.20000 AFIX 0 C40 1 0.518318 0.773422 0.064295 11.00000 0.08512 0.08231 = 0.07835 -0.02095 -0.00911 0.00878 N1 3 -0.043830 0.844177 0.139484 11.00000 0.07045 0.06792 = 0.07940 -0.01680 -0.00083 -0.00195 N2 3 -0.048852 1.019558 0.110860 11.00000 0.07323 0.06999 = 0.09185 -0.01782 -0.00551 0.00215 N3 3 0.439356 0.347584 0.136922 11.00000 0.07508 0.07361 = 0.07318 -0.02093 -0.00644 0.00062 C26 1 0.563969 0.478609 0.102815 11.00000 0.08321 0.08193 = 0.10347 -0.01224 -0.00269 -0.00214 AFIX 43 H26 2 0.635569 0.516631 0.086723 11.00000 -1.20000 AFIX 0 O1 4 -0.223680 0.731278 0.274677 11.00000 0.07530 0.09844 = 0.07695 -0.03051 0.00353 0.00885 O2 4 0.307412 0.239746 0.299307 11.00000 0.08148 0.11118 = 0.09543 -0.03662 0.00988 0.01361 O3 4 -0.087638 0.225716 0.058840 11.00000 0.07583 0.06904 = 0.11394 -0.01294 -0.01657 -0.00101 AFIX 147 H3A 2 -0.072287 0.160954 0.066950 11.00000 -1.50000 AFIX 0 O4 4 0.111875 0.225760 0.082822 11.00000 0.07406 0.07789 = 0.15135 -0.00105 -0.02218 0.00162 O5 4 0.410135 0.729752 0.082998 11.00000 0.08728 0.07376 = 0.12434 -0.01695 -0.00849 0.00003 AFIX 147 H5A 2 0.422313 0.665245 0.099121 11.00000 -1.50000 AFIX 0 O6 4 0.619389 0.724845 0.071406 11.00000 0.08686 0.07988 = 0.14313 -0.00841 -0.01422 0.01436 S2 5 0.618811 0.343956 0.460048 11.00000 0.18635 0.19519 = 0.11972 -0.03738 -0.03873 -0.02725 CL1 6 0.141016 0.557749 0.273258 11.00000 0.07525 0.10217 = 0.22421 -0.05218 -0.00607 0.01230 CL2 6 -0.097817 0.207290 0.282634 11.00000 0.26083 0.07575 = 0.11742 -0.01856 -0.00999 -0.04006 CL4 6 0.644618 0.063574 0.205997 11.00000 0.07120 0.09924 = 0.13992 -0.02421 0.00848 0.00509 CL5 6 0.391230 -0.286981 0.298376 11.00000 0.23097 0.08848 = 0.12976 -0.00580 -0.04294 -0.04993 C23 1 0.405047 0.191566 0.250849 11.00000 0.06446 0.08632 = 0.07206 -0.02805 0.00429 0.00323 AFIX 13 H23 2 0.485891 0.207115 0.267089 11.00000 -1.20000 AFIX 0 HKLF 4 REM SD20200318j_Cu in P-1 REM wR2 = 0.3330, GooF = S = 1.187, Restrained GooF = 1.187 for all data REM R1 = 0.0958 for 5232 Fo > 4sig(Fo) and 0.1246 for all 8208 data REM 543 parameters refined using 0 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 0.724, deepest hole -0.501, 1-sigma level 0.097 Q1 1 0.2823 -0.2627 0.3165 11.00000 0.05 0.72 Q2 1 -0.2045 0.2316 0.2740 11.00000 0.05 0.59 Q3 1 -0.1023 0.8318 0.4225 11.00000 0.05 0.54 Q4 1 -0.1438 0.7161 0.4244 11.00000 0.05 0.50 Q5 1 -0.1595 0.3626 0.2782 11.00000 0.05 0.40 ; _shelx_res_checksum 61790 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 C15A C -0.1401(17) 0.9229(11) 0.3667(10) 0.115(4) Uiso 0.50(2) 1 d . . P A 2 C16A C -0.0687(19) 0.9384(12) 0.4142(10) 0.134(5) Uiso 0.50(2) 1 d . . P A 2 S1A S 0.0196(13) 0.8248(16) 0.4805(8) 0.167(5) Uani 0.50(2) 1 d . . P A 2 Cl3B Cl -0.0406(14) 0.6225(5) 0.4929(6) 0.171(4) Uani 0.50(2) 1 d . . P A 2 C15B C -0.2044(16) 0.9064(10) 0.3834(8) 0.111(4) Uiso 0.50(2) 1 d . . P A 1 C16B C -0.1458(19) 0.9520(11) 0.4134(10) 0.127(5) Uiso 0.50(2) 1 d . . P A 1 S1B S -0.0142(12) 0.8641(9) 0.4753(8) 0.135(3) Uani 0.50(2) 1 d . . P A 1 Cl3A Cl 0.0030(16) 0.6382(12) 0.4820(10) 0.242(6) Uani 0.50(2) 1 d . . P A 1 C1 C -0.1051(4) 0.5655(3) 0.2541(2) 0.0738(9) Uani 1 1 d . . . . . C2 C 0.0027(4) 0.5010(3) 0.2683(3) 0.0850(11) Uani 1 1 d . . . . . C3 C 0.0062(6) 0.3903(4) 0.2749(3) 0.1019(14) Uani 1 1 d . . . . . H3 H 0.081070 0.348868 0.282577 0.122 Uiso 1 1 calc R U . . . C4 C -0.0988(7) 0.3457(4) 0.2701(3) 0.1059(15) Uani 1 1 d . . . . . C5 C -0.2115(6) 0.4066(5) 0.2556(4) 0.1132(16) Uani 1 1 d . . . . . H5 H -0.284164 0.374120 0.251373 0.136 Uiso 1 1 calc R U . . . C6 C -0.2130(5) 0.5155(4) 0.2476(3) 0.1009(13) Uani 1 1 d . . . . . H6 H -0.287474 0.556643 0.237738 0.121 Uiso 1 1 calc R U . . . C7 C -0.1061(3) 0.6854(3) 0.2446(2) 0.0721(9) Uani 1 1 d . . . . . H7 H -0.039848 0.703086 0.275841 0.086 Uiso 1 1 calc R U . . . C8 C -0.0827(4) 0.7365(3) 0.1505(2) 0.0768(9) Uani 1 1 d . . . . . H8A H -0.018045 0.693699 0.123026 0.092 Uiso 1 1 calc R U . . . H8B H -0.159054 0.737732 0.122992 0.092 Uiso 1 1 calc R U . . . C9 C -0.1098(4) 0.9358(3) 0.1121(3) 0.0772(10) Uani 1 1 d . . . . . H9 H -0.190675 0.939167 0.095584 0.093 Uiso 1 1 calc R U . . . C10 C 0.0634(4) 0.9805(4) 0.1393(3) 0.0975(13) Uani 1 1 d . . . . . H10 H 0.127611 1.021656 0.145937 0.117 Uiso 1 1 calc R U . . . C11 C 0.0680(4) 0.8746(4) 0.1564(4) 0.1060(16) Uani 1 1 d . . . . . H11 H 0.135341 0.829467 0.176264 0.127 Uiso 1 1 calc R U . . . C12 C -0.2432(4) 0.7144(4) 0.3660(3) 0.0929(12) Uani 1 1 d . . . . . H12A H -0.225016 0.639577 0.389593 0.111 Uiso 1 1 calc R U . . . H12B H -0.330524 0.732699 0.383228 0.111 Uiso 1 1 calc R U . . . C13 C -0.0710(6) 0.7555(6) 0.4480(4) 0.129(2) Uani 1 1 d . . . . . C14 C -0.1607(5) 0.7806(5) 0.4008(3) 0.1118(16) Uani 1 1 d . . . . . C17 C 0.3987(4) 0.0707(3) 0.2638(2) 0.0759(9) Uani 1 1 d . . . . . C18 C 0.5037(4) 0.0061(3) 0.2444(3) 0.0787(10) Uani 1 1 d . . . . . C19 C 0.5032(5) -0.1033(3) 0.2541(3) 0.0910(12) Uani 1 1 d . . . . . H19 H 0.575505 -0.144127 0.240165 0.109 Uiso 1 1 calc R U . . . C20 C 0.3952(6) -0.1490(4) 0.2844(3) 0.1001(13) Uani 1 1 d . . . . . C21 C 0.2864(6) -0.0893(5) 0.3037(3) 0.1138(17) Uani 1 1 d . . . . . H21 H 0.212071 -0.122298 0.323670 0.137 Uiso 1 1 calc R U . . . C22 C 0.2894(4) 0.0211(4) 0.2929(3) 0.1007(13) Uani 1 1 d . . . . . H22 H 0.216345 0.061689 0.305669 0.121 Uiso 1 1 calc R U . . . Cl6 Cl 0.5690(3) 0.12082(19) 0.48389(19) 0.2215(13) Uani 1 1 d . . . . . C24 C 0.3945(4) 0.2424(3) 0.1585(2) 0.0775(9) Uani 1 1 d . . . . . H24A H 0.442378 0.197804 0.122539 0.093 Uiso 1 1 calc R U . . . H24B H 0.307247 0.246135 0.146935 0.093 Uiso 1 1 calc R U . . . C27 C 0.5604(4) 0.3722(3) 0.1100(3) 0.0888(11) Uani 1 1 d . . . . . H27 H 0.627641 0.324644 0.098731 0.107 Uiso 1 1 calc R U . . . N4 N 0.4460(3) 0.5220(3) 0.1229(2) 0.0857(9) Uani 1 1 d . . . . . C25 C 0.3763(4) 0.4409(3) 0.1426(3) 0.0878(11) Uani 1 1 d . . . . . H25 H 0.290597 0.447138 0.159234 0.105 Uiso 1 1 calc R U . . . C28 C 0.3234(6) 0.2219(5) 0.3881(3) 0.1171(17) Uani 1 1 d . . . . . H28A H 0.344677 0.146724 0.408164 0.140 Uiso 1 1 calc R U . . . H28B H 0.244809 0.240886 0.419166 0.140 Uiso 1 1 calc R U . . . C29 C 0.5257(8) 0.2478(5) 0.4467(4) 0.132(2) Uani 1 1 d . . . . . C30 C 0.4251(6) 0.2860(4) 0.4064(3) 0.1088(16) Uani 1 1 d . . . . . C31 C 0.4230(8) 0.4043(6) 0.3839(5) 0.143(2) Uani 1 1 d . . . . . H31 H 0.360099 0.446600 0.355456 0.172 Uiso 1 1 calc R U . . . C32 C 0.5168(11) 0.4417(6) 0.4078(6) 0.176(3) Uani 1 1 d . . . . . H32 H 0.529357 0.514105 0.398109 0.212 Uiso 1 1 calc R U . . . C33 C 0.0047(3) 0.3900(3) 0.0286(2) 0.0666(8) Uani 1 1 d . . . . . C34 C -0.1077(3) 0.4464(3) 0.0114(3) 0.0838(11) Uani 1 1 d . . . . . H34 H -0.181247 0.410785 0.018888 0.101 Uiso 1 1 calc R U . . . C35 C 0.1119(4) 0.4456(3) 0.0165(3) 0.0866(11) Uani 1 1 d . . . . . H35 H 0.188687 0.408841 0.027501 0.104 Uiso 1 1 calc R U . . . C36 C 0.0155(3) 0.2727(3) 0.0600(2) 0.0753(9) Uani 1 1 d . . . . . C37 C 0.5070(3) 0.8906(3) 0.0309(2) 0.0715(9) Uani 1 1 d . . . . . C38 C 0.3928(4) 0.9506(3) 0.0388(3) 0.0784(10) Uani 1 1 d . . . . . H38 H 0.320964 0.917279 0.064790 0.094 Uiso 1 1 calc R U . . . C39 C 0.6136(4) 0.9413(3) -0.0082(3) 0.0770(9) Uani 1 1 d . . . . . H39 H 0.689845 0.901737 -0.013724 0.092 Uiso 1 1 calc R U . . . C40 C 0.5183(4) 0.7734(3) 0.0643(3) 0.0819(10) Uani 1 1 d . . . . . N1 N -0.0438(3) 0.8442(2) 0.1395(2) 0.0728(8) Uani 1 1 d . . . . . N2 N -0.0489(3) 1.0196(3) 0.1109(2) 0.0786(8) Uani 1 1 d . . . . . N3 N 0.4394(3) 0.3476(2) 0.13692(19) 0.0734(8) Uani 1 1 d . . . . . C26 C 0.5640(4) 0.4786(3) 0.1028(3) 0.0910(12) Uani 1 1 d . . . . . H26 H 0.635569 0.516631 0.086723 0.109 Uiso 1 1 calc R U . . . O1 O -0.2237(2) 0.7313(2) 0.27468(16) 0.0833(7) Uani 1 1 d . . . . . O2 O 0.3074(3) 0.2397(2) 0.29931(19) 0.0963(9) Uani 1 1 d . . . . . O3 O -0.0876(2) 0.2257(2) 0.0588(2) 0.0866(8) Uani 1 1 d . . . . . H3A H -0.072287 0.160954 0.066950 0.130 Uiso 1 1 calc R U . . . O4 O 0.1119(3) 0.2258(2) 0.0828(3) 0.1035(10) Uani 1 1 d . . . . . O5 O 0.4101(3) 0.7298(2) 0.0830(2) 0.0958(9) Uani 1 1 d . . . . . H5A H 0.422313 0.665245 0.099121 0.144 Uiso 1 1 calc R U . . . O6 O 0.6194(3) 0.7248(2) 0.0714(2) 0.1060(10) Uani 1 1 d . . . . . S2 S 0.6188(2) 0.3440(2) 0.46005(12) 0.1634(8) Uani 1 1 d . . . . . Cl1 Cl 0.14102(11) 0.55775(11) 0.27326(13) 0.1327(7) Uani 1 1 d . . . . . Cl2 Cl -0.0978(2) 0.20729(10) 0.28263(10) 0.1502(8) Uani 1 1 d . . . . . Cl4 Cl 0.64462(10) 0.06357(9) 0.20600(9) 0.1053(5) Uani 1 1 d . . . . . Cl5 Cl 0.3912(2) -0.28698(11) 0.29838(11) 0.1476(7) Uani 1 1 d . . . . . C23 C 0.4050(3) 0.1916(3) 0.2508(2) 0.0738(9) Uani 1 1 d . . . . . H23 H 0.485891 0.207115 0.267089 0.089 Uiso 1 1 calc R U . . . 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 S1A 0.150(6) 0.268(13) 0.102(3) -0.070(6) -0.009(3) -0.040(7) Cl3B 0.255(10) 0.110(4) 0.138(4) -0.027(2) -0.041(4) 0.070(3) S1B 0.140(6) 0.165(5) 0.120(3) -0.056(3) -0.012(4) -0.044(4) Cl3A 0.205(8) 0.307(13) 0.224(10) -0.095(8) -0.087(7) 0.126(7) C1 0.080(2) 0.072(2) 0.0715(19) -0.0227(16) 0.0022(16) -0.0082(18) C2 0.093(3) 0.071(2) 0.091(2) -0.0242(18) 0.006(2) -0.003(2) C3 0.124(4) 0.081(3) 0.099(3) -0.024(2) 0.004(3) 0.003(3) C4 0.158(5) 0.083(3) 0.078(3) -0.017(2) -0.002(3) -0.022(3) C5 0.135(4) 0.106(4) 0.108(3) -0.025(3) -0.018(3) -0.043(3) C6 0.107(3) 0.098(3) 0.105(3) -0.018(2) -0.028(3) -0.022(3) C7 0.0683(19) 0.079(2) 0.0696(19) -0.0232(16) 0.0014(15) -0.0008(16) C8 0.085(2) 0.077(2) 0.071(2) -0.0241(16) 0.0026(17) -0.0032(18) C9 0.0698(19) 0.077(2) 0.086(2) -0.0213(18) -0.0099(17) 0.0080(19) C10 0.073(2) 0.082(3) 0.134(4) -0.008(2) -0.017(2) -0.006(2) C11 0.069(2) 0.081(3) 0.161(5) -0.002(3) -0.026(3) -0.001(2) C12 0.094(3) 0.108(3) 0.080(2) -0.034(2) 0.012(2) -0.009(2) C13 0.117(4) 0.175(6) 0.096(3) -0.051(4) 0.006(3) 0.014(4) C14 0.114(4) 0.149(5) 0.072(2) -0.035(3) 0.010(3) 0.000(3) C17 0.073(2) 0.082(2) 0.074(2) -0.0168(17) -0.0039(16) -0.0099(18) C18 0.075(2) 0.081(2) 0.080(2) -0.0141(18) -0.0094(17) -0.0024(18) C19 0.105(3) 0.077(3) 0.090(3) -0.013(2) -0.017(2) 0.001(2) C20 0.130(4) 0.090(3) 0.082(3) -0.011(2) -0.021(3) -0.020(3) C21 0.117(4) 0.123(4) 0.105(3) -0.011(3) -0.008(3) -0.056(4) C22 0.071(2) 0.119(4) 0.113(3) -0.025(3) 0.007(2) -0.021(2) Cl6 0.289(3) 0.1438(16) 0.212(3) 0.0199(16) -0.070(2) 0.0345(19) C24 0.078(2) 0.077(2) 0.080(2) -0.0200(17) -0.0087(17) -0.0071(18) C27 0.084(2) 0.073(2) 0.105(3) -0.016(2) -0.001(2) 0.0027(19) N4 0.093(2) 0.073(2) 0.091(2) -0.0202(16) -0.0039(17) 0.0025(18) C25 0.081(2) 0.083(3) 0.098(3) -0.025(2) -0.001(2) 0.008(2) C28 0.125(4) 0.143(5) 0.083(3) -0.039(3) 0.026(3) -0.017(4) C29 0.186(6) 0.119(4) 0.086(3) -0.018(3) -0.006(4) 0.006(4) C30 0.140(4) 0.114(4) 0.070(2) -0.034(2) 0.009(3) 0.019(3) C31 0.164(6) 0.124(5) 0.147(6) -0.041(4) -0.038(5) 0.022(5) C32 0.237(10) 0.131(6) 0.178(8) -0.061(5) -0.039(7) -0.009(6) C33 0.0608(17) 0.072(2) 0.0661(17) -0.0166(15) -0.0005(14) 0.0022(15) C34 0.0604(18) 0.075(2) 0.112(3) -0.013(2) -0.0021(19) -0.0003(17) C35 0.063(2) 0.075(2) 0.117(3) -0.012(2) -0.0065(19) 0.0063(18) C36 0.066(2) 0.080(2) 0.078(2) -0.0166(17) -0.0011(16) 0.0050(18) C37 0.076(2) 0.072(2) 0.0689(18) -0.0226(15) -0.0125(16) 0.0073(17) C38 0.073(2) 0.079(2) 0.086(2) -0.0252(18) -0.0050(17) 0.0033(18) C39 0.071(2) 0.076(2) 0.089(2) -0.0272(18) -0.0099(17) 0.0049(18) C40 0.085(3) 0.082(2) 0.078(2) -0.0209(18) -0.0091(19) 0.009(2) N1 0.0705(17) 0.0679(17) 0.0794(17) -0.0168(13) -0.0008(13) -0.0019(14) N2 0.0732(17) 0.0700(18) 0.092(2) -0.0178(15) -0.0055(15) 0.0021(15) N3 0.0751(17) 0.0736(19) 0.0732(17) -0.0209(13) -0.0064(13) 0.0006(15) C26 0.083(2) 0.082(3) 0.103(3) -0.012(2) -0.003(2) -0.002(2) O1 0.0753(14) 0.0984(18) 0.0770(15) -0.0305(13) 0.0035(12) 0.0089(13) O2 0.0815(16) 0.111(2) 0.0954(19) -0.0366(16) 0.0099(14) 0.0136(15) O3 0.0758(16) 0.0690(15) 0.114(2) -0.0129(15) -0.0166(14) -0.0010(13) O4 0.0741(16) 0.0779(17) 0.151(3) -0.0010(17) -0.0222(17) 0.0016(14) O5 0.0873(19) 0.0738(16) 0.124(2) -0.0169(16) -0.0085(16) 0.0000(14) O6 0.0869(19) 0.0799(18) 0.143(3) -0.0084(17) -0.0142(18) 0.0144(15) S2 0.1864(19) 0.195(2) 0.1197(12) -0.0374(12) -0.0387(12) -0.0272(16) Cl1 0.0752(7) 0.1022(9) 0.2242(18) -0.0522(10) -0.0061(8) 0.0123(6) Cl2 0.261(2) 0.0758(8) 0.1174(10) -0.0186(7) -0.0100(12) -0.0401(10) Cl4 0.0712(6) 0.0992(8) 0.1399(10) -0.0242(7) 0.0085(6) 0.0051(5) Cl5 0.231(2) 0.0885(9) 0.1298(11) -0.0058(7) -0.0429(12) -0.0499(11) C23 0.0645(18) 0.086(2) 0.0721(19) -0.0280(17) 0.0043(15) 0.0032(16) 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 C16A C15A C14 102.4(11) . . ? C15A C16A S1A 121.2(13) . . ? C13 S1A C16A 83.4(8) . . ? C16B C15B C14 111.5(12) . . ? C15B C16B S1B 113.8(12) . . ? C13 S1B C16B 87.5(7) . . ? C2 C1 C6 116.9(4) . . ? C2 C1 C7 121.6(4) . . ? C6 C1 C7 121.5(4) . . ? C1 C2 C3 122.4(4) . . ? C1 C2 Cl1 119.5(3) . . ? C3 C2 Cl1 118.1(4) . . ? C4 C3 C2 118.8(5) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 121.6(5) . . ? C3 C4 Cl2 119.5(5) . . ? C5 C4 Cl2 118.8(5) . . ? C6 C5 C4 118.8(5) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C5 C6 C1 121.3(5) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? O1 C7 C1 112.6(3) . . ? O1 C7 C8 106.4(3) . . ? C1 C7 C8 109.8(3) . . ? O1 C7 H7 109.3 . . ? C1 C7 H7 109.3 . . ? C8 C7 H7 109.3 . . ? N1 C8 C7 111.7(3) . . ? N1 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? N1 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? N2 C9 N1 113.0(4) . . ? N2 C9 H9 123.5 . . ? N1 C9 H9 123.5 . . ? C11 C10 N2 109.8(4) . . ? C11 C10 H10 125.1 . . ? N2 C10 H10 125.1 . . ? C10 C11 N1 107.6(4) . . ? C10 C11 H11 126.2 . . ? N1 C11 H11 126.2 . . ? O1 C12 C14 111.1(4) . . ? O1 C12 H12A 109.4 . . ? C14 C12 H12A 109.4 . . ? O1 C12 H12B 109.4 . . ? C14 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C14 C13 S1A 132.0(9) . . ? C14 C13 Cl3A 130.7(8) . . ? C14 C13 S1B 112.9(7) . . ? Cl3A C13 S1B 116.3(7) . . ? C14 C13 Cl3B 118.7(7) . . ? S1A C13 Cl3B 109.2(7) . . ? C13 C14 C12 132.0(6) . . ? C13 C14 C15B 114.2(7) . . ? C12 C14 C15B 113.4(7) . . ? C13 C14 C15A 99.2(7) . . ? C12 C14 C15A 127.6(6) . . ? C22 C17 C18 116.8(4) . . ? C22 C17 C23 122.3(4) . . ? C18 C17 C23 120.9(3) . . ? C19 C18 C17 123.4(4) . . ? C19 C18 Cl4 117.3(3) . . ? C17 C18 Cl4 119.3(3) . . ? C20 C19 C18 118.0(4) . . ? C20 C19 H19 121.0 . . ? C18 C19 H19 121.0 . . ? C19 C20 C21 121.7(5) . . ? C19 C20 Cl5 119.3(5) . . ? C21 C20 Cl5 119.0(4) . . ? C20 C21 C22 119.2(4) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C17 C22 C21 121.0(5) . . ? C17 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? N3 C24 C23 112.7(3) . . ? N3 C24 H24A 109.1 . . ? C23 C24 H24A 109.1 . . ? N3 C24 H24B 109.1 . . ? C23 C24 H24B 109.1 . . ? H24A C24 H24B 107.8 . . ? C26 C27 N3 107.0(4) . . ? C26 C27 H27 126.5 . . ? N3 C27 H27 126.5 . . ? C25 N4 C26 104.5(3) . . ? N4 C25 N3 113.7(4) . . ? N4 C25 H25 123.1 . . ? N3 C25 H25 123.1 . . ? O2 C28 C30 112.1(4) . . ? O2 C28 H28A 109.2 . . ? C30 C28 H28A 109.2 . . ? O2 C28 H28B 109.2 . . ? C30 C28 H28B 109.2 . . ? H28A C28 H28B 107.9 . . ? C30 C29 Cl6 127.7(6) . . ? C30 C29 S2 113.9(5) . . ? Cl6 C29 S2 118.3(5) . . ? C29 C30 C31 109.9(6) . . ? C29 C30 C28 126.4(6) . . ? C31 C30 C28 123.7(6) . . ? C32 C31 C30 112.8(7) . . ? C32 C31 H31 123.6 . . ? C30 C31 H31 123.6 . . ? C31 C32 S2 113.5(7) . . ? C31 C32 H32 123.3 . . ? S2 C32 H32 123.3 . . ? C34 C33 C35 118.1(3) . . ? C34 C33 C36 123.1(3) . . ? C35 C33 C36 118.8(3) . . ? C35 C34 C33 120.5(4) 2_565 . ? C35 C34 H34 119.8 2_565 . ? C33 C34 H34 119.8 . . ? C34 C35 C33 121.4(4) 2_565 . ? C34 C35 H35 119.3 2_565 . ? C33 C35 H35 119.3 . . ? O4 C36 O3 123.6(4) . . ? O4 C36 C33 122.5(4) . . ? O3 C36 C33 113.9(3) . . ? C39 C37 C38 119.4(3) . . ? C39 C37 C40 118.8(3) . . ? C38 C37 C40 121.8(4) . . ? C39 C38 C37 120.1(4) 2_675 . ? C39 C38 H38 119.9 2_675 . ? C37 C38 H38 119.9 . . ? C38 C39 C37 120.5(3) 2_675 . ? C38 C39 H39 119.8 2_675 . ? C37 C39 H39 119.8 . . ? O6 C40 O5 124.4(4) . . ? O6 C40 C37 121.8(4) . . ? O5 C40 C37 113.9(3) . . ? C9 N1 C11 104.6(3) . . ? C9 N1 C8 128.0(3) . . ? C11 N1 C8 127.3(3) . . ? C9 N2 C10 104.9(3) . . ? C25 N3 C27 105.2(4) . . ? C25 N3 C24 128.7(4) . . ? C27 N3 C24 126.0(3) . . ? C27 C26 N4 109.6(4) . . ? C27 C26 H26 125.2 . . ? N4 C26 H26 125.2 . . ? C7 O1 C12 112.9(3) . . ? C23 O2 C28 113.7(4) . . ? C36 O3 H3A 109.5 . . ? C40 O5 H5A 109.5 . . ? C29 S2 C32 89.8(4) . . ? O2 C23 C24 106.9(3) . . ? O2 C23 C17 112.8(3) . . ? C24 C23 C17 110.5(3) . . ? O2 C23 H23 108.9 . . ? C24 C23 H23 108.9 . . ? C17 C23 H23 108.9 . . ? 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 C15A C16A 1.19(2) . ? C15A C14 1.824(15) . ? C16A S1A 1.88(2) . ? S1A C13 1.566(15) . ? Cl3B C13 1.734(9) . ? C15B C16B 1.101(18) . ? C15B C14 1.620(13) . ? C16B S1B 1.960(19) . ? S1B C13 1.717(13) . ? Cl3A C13 1.661(13) . ? C1 C2 1.375(6) . ? C1 C6 1.393(6) . ? C1 C7 1.515(5) . ? C2 C3 1.401(6) . ? C2 Cl1 1.724(5) . ? C3 C4 1.323(8) . ? C3 H3 0.9300 . ? C4 C5 1.398(8) . ? C4 Cl2 1.745(5) . ? C5 C6 1.376(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.422(4) . ? C7 C8 1.525(5) . ? C7 H7 0.9800 . ? C8 N1 1.449(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.300(5) . ? C9 N1 1.340(5) . ? C9 H9 0.9300 . ? C10 C11 1.328(6) . ? C10 N2 1.356(5) . ? C10 H10 0.9300 . ? C11 N1 1.364(5) . ? C11 H11 0.9300 . ? C12 O1 1.434(5) . ? C12 C14 1.497(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.271(8) . ? C17 C22 1.373(6) . ? C17 C18 1.385(5) . ? C17 C23 1.529(6) . ? C18 C19 1.382(6) . ? C18 Cl4 1.736(4) . ? C19 C20 1.342(7) . ? C19 H19 0.9300 . ? C20 C21 1.381(8) . ? C20 Cl5 1.743(5) . ? C21 C22 1.395(7) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? Cl6 C29 1.665(7) . ? C24 N3 1.435(5) . ? C24 C23 1.508(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C27 C26 1.350(6) . ? C27 N3 1.366(5) . ? C27 H27 0.9300 . ? N4 C25 1.301(6) . ? N4 C26 1.370(5) . ? C25 N3 1.338(5) . ? C25 H25 0.9300 . ? C28 O2 1.425(6) . ? C28 C30 1.507(9) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.327(9) . ? C29 S2 1.711(8) . ? C30 C31 1.488(9) . ? C31 C32 1.277(11) . ? C31 H31 0.9300 . ? C32 S2 1.739(10) . ? C32 H32 0.9300 . ? C33 C34 1.378(5) . ? C33 C35 1.381(6) . ? C33 C36 1.487(5) . ? C34 C35 1.366(5) 2_565 ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 O4 1.207(4) . ? C36 O3 1.308(5) . ? C37 C39 1.390(6) . ? C37 C38 1.398(5) . ? C37 C40 1.491(5) . ? C38 C39 1.375(5) 2_675 ? C38 H38 0.9300 . ? C39 H39 0.9300 . ? C40 O6 1.209(5) . ? C40 O5 1.311(5) . ? C26 H26 0.9300 . ? O2 C23 1.409(4) . ? O3 H3A 0.8200 . ? O5 H5A 0.8200 . ? C23 H23 0.9800 . ? 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 C14 C15A C16A S1A 13.7(18) . . . . ? C15A C16A S1A C13 -9.8(17) . . . . ? C14 C15B C16B S1B -0.2(17) . . . . ? C6 C1 C2 C3 0.9(6) . . . . ? C7 C1 C2 C3 -178.2(4) . . . . ? C6 C1 C2 Cl1 177.7(3) . . . . ? C7 C1 C2 Cl1 -1.4(5) . . . . ? C1 C2 C3 C4 -2.2(7) . . . . ? Cl1 C2 C3 C4 -179.1(4) . . . . ? C2 C3 C4 C5 2.3(7) . . . . ? C2 C3 C4 Cl2 -177.3(3) . . . . ? C3 C4 C5 C6 -1.1(8) . . . . ? Cl2 C4 C5 C6 178.5(4) . . . . ? C4 C5 C6 C1 -0.3(8) . . . . ? C2 C1 C6 C5 0.3(7) . . . . ? C7 C1 C6 C5 179.4(4) . . . . ? C2 C1 C7 O1 -148.8(4) . . . . ? C6 C1 C7 O1 32.1(5) . . . . ? C2 C1 C7 C8 92.9(4) . . . . ? C6 C1 C7 C8 -86.2(4) . . . . ? O1 C7 C8 N1 76.0(4) . . . . ? C1 C7 C8 N1 -161.9(3) . . . . ? N2 C10 C11 N1 -0.6(6) . . . . ? C16A S1A C13 C14 -2.1(10) . . . . ? C16A S1A C13 Cl3B -178.3(7) . . . . ? C16B S1B C13 C14 2.9(8) . . . . ? C16B S1B C13 Cl3A 179.8(9) . . . . ? S1A C13 C14 C12 176.4(7) . . . . ? Cl3A C13 C14 C12 7.9(13) . . . . ? S1B C13 C14 C12 -175.8(6) . . . . ? Cl3B C13 C14 C12 -7.7(9) . . . . ? Cl3A C13 C14 C15B -180.0(10) . . . . ? S1B C13 C14 C15B -3.7(9) . . . . ? S1A C13 C14 C15A 8.3(10) . . . . ? Cl3B C13 C14 C15A -175.8(7) . . . . ? O1 C12 C14 C13 -115.4(6) . . . . ? O1 C12 C14 C15B 72.4(7) . . . . ? O1 C12 C14 C15A 49.7(9) . . . . ? C16B C15B C14 C13 2.5(16) . . . . ? C16B C15B C14 C12 176.2(12) . . . . ? C16A C15A C14 C13 -12.7(13) . . . . ? C16A C15A C14 C12 178.4(10) . . . . ? C22 C17 C18 C19 -1.0(6) . . . . ? C23 C17 C18 C19 -179.5(4) . . . . ? C22 C17 C18 Cl4 179.2(3) . . . . ? C23 C17 C18 Cl4 0.7(5) . . . . ? C17 C18 C19 C20 -0.3(6) . . . . ? Cl4 C18 C19 C20 179.5(3) . . . . ? C18 C19 C20 C21 1.4(7) . . . . ? C18 C19 C20 Cl5 -179.5(3) . . . . ? C19 C20 C21 C22 -1.1(7) . . . . ? Cl5 C20 C21 C22 179.7(4) . . . . ? C18 C17 C22 C21 1.2(7) . . . . ? C23 C17 C22 C21 179.7(4) . . . . ? C20 C21 C22 C17 -0.2(8) . . . . ? C26 N4 C25 N3 -0.2(5) . . . . ? Cl6 C29 C30 C31 -179.7(5) . . . . ? S2 C29 C30 C31 0.2(6) . . . . ? Cl6 C29 C30 C28 2.5(8) . . . . ? S2 C29 C30 C28 -177.6(4) . . . . ? O2 C28 C30 C29 -123.7(6) . . . . ? O2 C28 C30 C31 58.7(6) . . . . ? C29 C30 C31 C32 0.1(9) . . . . ? C28 C30 C31 C32 178.0(7) . . . . ? C30 C31 C32 S2 -0.4(10) . . . . ? C35 C33 C34 C35 -0.3(7) . . . 2_565 ? C36 C33 C34 C35 179.4(4) . . . 2_565 ? C34 C33 C35 C34 0.3(7) . . . 2_565 ? C36 C33 C35 C34 -179.4(4) . . . 2_565 ? C34 C33 C36 O4 -172.5(4) . . . . ? C35 C33 C36 O4 7.1(6) . . . . ? C34 C33 C36 O3 8.8(5) . . . . ? C35 C33 C36 O3 -171.6(4) . . . . ? C39 C37 C38 C39 -0.1(6) . . . 2_675 ? C40 C37 C38 C39 179.1(4) . . . 2_675 ? C38 C37 C39 C38 0.1(6) . . . 2_675 ? C40 C37 C39 C38 -179.1(4) . . . 2_675 ? C39 C37 C40 O6 12.6(6) . . . . ? C38 C37 C40 O6 -166.6(4) . . . . ? C39 C37 C40 O5 -166.1(4) . . . . ? C38 C37 C40 O5 14.7(5) . . . . ? N2 C9 N1 C11 -0.2(5) . . . . ? N2 C9 N1 C8 178.7(3) . . . . ? C10 C11 N1 C9 0.5(5) . . . . ? C10 C11 N1 C8 -178.5(4) . . . . ? C7 C8 N1 C9 -108.4(4) . . . . ? C7 C8 N1 C11 70.3(5) . . . . ? N1 C9 N2 C10 -0.1(5) . . . . ? C11 C10 N2 C9 0.4(6) . . . . ? N4 C25 N3 C27 -0.7(5) . . . . ? N4 C25 N3 C24 176.0(3) . . . . ? C26 C27 N3 C25 1.3(5) . . . . ? C26 C27 N3 C24 -175.5(4) . . . . ? C23 C24 N3 C25 -88.1(5) . . . . ? C23 C24 N3 C27 88.0(4) . . . . ? N3 C27 C26 N4 -1.5(5) . . . . ? C25 N4 C26 C27 1.0(5) . . . . ? C1 C7 O1 C12 75.9(4) . . . . ? C8 C7 O1 C12 -163.8(3) . . . . ? C14 C12 O1 C7 71.7(5) . . . . ? C30 C28 O2 C23 73.3(6) . . . . ? C30 C29 S2 C32 -0.3(5) . . . . ? Cl6 C29 S2 C32 179.6(5) . . . . ? C31 C32 S2 C29 0.4(8) . . . . ? C28 O2 C23 C24 -164.2(4) . . . . ? C28 O2 C23 C17 74.2(5) . . . . ? N3 C24 C23 O2 75.8(4) . . . . ? N3 C24 C23 C17 -161.2(3) . . . . ? C22 C17 C23 O2 22.0(5) . . . . ? C18 C17 C23 O2 -159.6(4) . . . . ? C22 C17 C23 C24 -97.5(4) . . . . ? C18 C17 C23 C24 80.9(4) . . . . ?