#------------------------------------------------------------------------------ #$Date: 2023-11-15 01:36:00 +0200 (Wed, 15 Nov 2023) $ #$Revision: 287595 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247714.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_7247714 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 H13 Cl3 N2 O S, C6 H5 N O2' _chemical_formula_sum 'C22 H18 Cl3 N3 O3 S' _chemical_formula_weight 510.80 _chemical_name_common 'Tioconazole-Nicotinic 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 97.644(2) _cell_angle_beta 99.212(2) _cell_angle_gamma 90.462(2) _cell_formula_units_Z 4 _cell_length_a 8.0219(2) _cell_length_b 12.3226(3) _cell_length_c 23.9838(5) _cell_measurement_reflns_used 30291 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 72.5670 _cell_measurement_theta_min 3.6060 _cell_volume 2318.40(10) _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 'SIR-2011 (Burla et al., 2012)' _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 0.960 _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 0.1407 _diffrn_reflns_av_unetI/netI 0.0693 _diffrn_reflns_Laue_measured_fraction_full 0.983 _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 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 48662 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.960 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.776 _diffrn_reflns_theta_min 3.621 _diffrn_source MicroMax003_Cu _diffrn_source_current 0.6 _diffrn_source_power 0.0 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 4.677 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.13435 _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 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1048 _exptl_crystal_size_max 0.870 _exptl_crystal_size_mid 0.380 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.814 _refine_diff_density_min -0.798 _refine_diff_density_rms 0.147 _refine_ls_extinction_coef 0.0122(9) _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 1.086 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 582 _refine_ls_number_reflns 8855 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.086 _refine_ls_R_factor_all 0.0813 _refine_ls_R_factor_gt 0.0730 _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^)+(0.1318P)^2^+0.5409P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1879 _refine_ls_wR_factor_ref 0.2019 _reflns_Friedel_coverage 0.000 _reflns_number_gt 7791 _reflns_number_total 8855 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00948c2.cif _cod_data_source_block TCZ_NICA _cod_database_code 7247714 _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 0.106 _shelx_estimated_absorpt_t_max 0.604 _shelx_res_file ; TITL SIR2011 run in space group P -1 shelx.res created by SHELXL-2018/3 at 14:27:23 on 26-Jul-2022 CELL 1.54184 8.0219 12.3226 23.9838 97.644 99.212 90.462 ZERR 4.00 0.0002 0.0003 0.0005 0.002 0.002 0.002 LATT 1 SFAC C H N O S CL UNIT 88 72 12 12 4 12 MERG 2 OMIT 0 0 7 OMIT 0 0 1 OMIT -1 -3 1 FMAP 2 PLAN 5 SIZE 0.120 0.380 0.870 ACTA BOND $H CONF L.S. 10 TEMP 20.00 WGHT 0.131800 0.540900 EXTI 0.012204 FVAR 3.57410 C1 1 0.739380 0.621379 0.318237 11.00000 0.04709 0.04104 = 0.04585 0.01528 0.01631 0.00527 C2 1 0.662930 0.723092 0.318553 11.00000 0.04928 0.04112 = 0.04917 0.01689 0.01673 0.00725 C3 1 0.695736 0.804747 0.364339 11.00000 0.06105 0.03869 = 0.05712 0.01379 0.02246 0.00803 AFIX 43 H3 2 0.643463 0.871717 0.363391 11.00000 -1.20000 AFIX 0 C4 1 0.808485 0.784984 0.411942 11.00000 0.06329 0.04518 = 0.05168 0.00728 0.01860 -0.00235 C5 1 0.888158 0.686565 0.413293 11.00000 0.05558 0.05402 = 0.04862 0.01428 0.00699 0.00189 AFIX 43 H5 2 0.964216 0.674326 0.445249 11.00000 -1.20000 AFIX 0 C6 1 0.853960 0.606333 0.366750 11.00000 0.04939 0.04424 = 0.05084 0.01525 0.01164 0.00940 AFIX 43 H6 2 0.908836 0.540251 0.367702 11.00000 -1.20000 AFIX 0 C7 1 0.697918 0.529996 0.268973 11.00000 0.04785 0.03844 = 0.04582 0.01353 0.01515 0.00636 AFIX 13 H7 2 0.575689 0.526951 0.255705 11.00000 -1.20000 AFIX 0 C8 1 0.788433 0.546844 0.219083 11.00000 0.05776 0.04561 = 0.04604 0.01175 0.01836 0.00288 AFIX 23 H8A 2 0.779859 0.622501 0.212095 11.00000 -1.20000 H8B 2 0.907207 0.531416 0.228602 11.00000 -1.20000 AFIX 0 C9 1 0.734544 0.366845 0.155846 11.00000 0.09633 0.04463 = 0.05454 0.01008 0.01380 0.02034 AFIX 43 H9 2 0.810264 0.326749 0.177923 11.00000 -1.20000 AFIX 0 C10 1 0.545164 0.409756 0.089926 11.00000 0.08642 0.05977 = 0.06234 0.00398 0.00190 0.00440 AFIX 43 H10 2 0.464165 0.404606 0.057205 11.00000 -1.20000 AFIX 0 C11 1 0.591947 0.502400 0.125871 11.00000 0.07939 0.04796 = 0.06260 0.01332 0.00355 0.01334 AFIX 43 H11 2 0.549755 0.571779 0.122708 11.00000 -1.20000 AFIX 0 O1 4 0.748231 0.426484 0.284793 11.00000 0.04938 0.03841 = 0.05216 0.01769 0.02067 0.00721 C13 1 0.756173 0.267210 0.388724 11.00000 0.05616 0.05421 = 0.05322 0.02064 0.01787 0.00504 C14 1 0.696702 0.275968 0.333474 11.00000 0.04296 0.04489 = 0.05100 0.01637 0.01751 0.00058 C15 1 0.707503 0.174705 0.298741 11.00000 0.05110 0.05092 = 0.06166 0.00767 0.02115 -0.00608 AFIX 43 H15 2 0.673900 0.164020 0.259407 11.00000 -1.20000 AFIX 0 C16 1 0.772155 0.095033 0.329064 11.00000 0.06299 0.04310 = 0.10012 0.01765 0.03637 0.00210 AFIX 43 H16 2 0.786696 0.023671 0.312737 11.00000 -1.20000 AFIX 0 C17 1 0.229484 0.028615 0.315045 11.00000 0.04592 0.03557 = 0.04787 0.00910 0.01614 0.00161 C18 1 0.150066 -0.073598 0.313119 11.00000 0.04698 0.03653 = 0.04672 0.00650 0.01544 0.00038 C19 1 0.183419 -0.135676 0.357396 11.00000 0.06184 0.03438 = 0.05609 0.00951 0.02466 -0.00047 AFIX 43 H19 2 0.128593 -0.203207 0.355390 11.00000 -1.20000 AFIX 0 C20 1 0.299053 -0.095581 0.404342 11.00000 0.06594 0.04536 = 0.04740 0.01279 0.01868 0.00343 C21 1 0.382578 0.004684 0.407847 11.00000 0.06117 0.04856 = 0.04796 0.00915 0.00883 -0.00113 AFIX 43 H21 2 0.460970 0.030942 0.439834 11.00000 -1.20000 AFIX 0 C22 1 0.347338 0.064445 0.363199 11.00000 0.05091 0.04053 = 0.05360 0.01008 0.01300 -0.00468 AFIX 43 H22 2 0.404342 0.131239 0.365259 11.00000 -1.20000 AFIX 0 C23 1 0.188854 0.097772 0.266888 11.00000 0.04753 0.03582 = 0.04884 0.01003 0.01373 -0.00207 AFIX 13 H23 2 0.066547 0.094719 0.253777 11.00000 -1.20000 AFIX 0 C24 1 0.278028 0.057740 0.217006 11.00000 0.05695 0.04219 = 0.04783 0.01267 0.01480 0.00389 AFIX 23 H24A 2 0.397288 0.077898 0.226832 11.00000 -1.20000 H24B 2 0.267353 -0.021487 0.208983 11.00000 -1.20000 AFIX 0 C25 1 0.227239 0.208405 0.156026 11.00000 0.10099 0.04825 = 0.05630 0.01559 0.01326 -0.01631 AFIX 43 H25 2 0.302709 0.259641 0.179093 11.00000 -1.20000 AFIX 0 C26 1 0.040863 0.132545 0.088173 11.00000 0.08425 0.05875 = 0.06471 0.02183 0.00121 -0.00176 AFIX 43 H26 2 -0.037893 0.121149 0.054842 11.00000 -1.20000 AFIX 0 C27 1 0.085742 0.057224 0.123448 11.00000 0.07399 0.04394 = 0.06502 0.01573 0.00383 -0.00560 AFIX 43 H27 2 0.043105 -0.014341 0.119134 11.00000 -1.20000 AFIX 0 C28 1 0.124917 0.272046 0.313779 11.00000 0.04971 0.04180 = 0.07332 0.00425 0.02374 0.00098 AFIX 23 H28A 2 0.093998 0.234069 0.343724 11.00000 -1.20000 H28B 2 0.023341 0.280780 0.286975 11.00000 -1.20000 AFIX 0 C29 1 0.263700 0.411056 0.394679 11.00000 0.06223 0.05529 = 0.06186 0.00759 0.02364 0.00527 C30 1 0.202428 0.381227 0.338677 11.00000 0.04496 0.04066 = 0.05868 0.00963 0.02159 0.00688 C31 1 0.220019 0.469741 0.307410 11.00000 0.05362 0.05153 = 0.07033 0.01965 0.02549 0.01361 AFIX 43 H31 2 0.186846 0.465701 0.268199 11.00000 -1.20000 AFIX 0 C32 1 0.290983 0.561107 0.341428 11.00000 0.06314 0.03713 = 0.13081 0.02375 0.04380 0.00891 AFIX 43 H32 2 0.310461 0.626619 0.327915 11.00000 -1.20000 AFIX 0 C33 1 0.174411 0.604830 0.098503 11.00000 0.06076 0.04788 = 0.04677 0.01470 0.01078 0.00815 C37 1 0.192414 0.615156 0.043158 11.00000 0.09171 0.05223 = 0.04882 0.01519 0.01563 0.01337 AFIX 43 H37 2 0.179091 0.554436 0.015136 11.00000 -1.20000 AFIX 0 C35 1 0.245747 0.804533 0.072403 11.00000 0.09677 0.05543 = 0.09509 0.02569 0.02806 -0.00192 AFIX 43 H35 2 0.272198 0.872922 0.063236 11.00000 -1.20000 AFIX 0 N5 3 0.225136 0.797950 0.125766 11.00000 0.11214 0.05060 = 0.08170 0.00340 0.02380 -0.00541 C34 1 0.190896 0.698615 0.137465 11.00000 0.08720 0.05683 = 0.05360 0.00747 0.01765 0.00255 AFIX 43 H34 2 0.177054 0.691887 0.174629 11.00000 -1.20000 AFIX 0 C38 1 0.141590 0.496462 0.116817 11.00000 0.07163 0.05367 = 0.04683 0.01781 0.01378 0.00874 C39 1 0.669434 -0.058533 0.095565 11.00000 0.05835 0.04844 = 0.04767 0.00713 0.00856 -0.00376 C40 1 0.680815 -0.131116 0.135236 11.00000 0.08267 0.05995 = 0.05428 0.01554 0.01467 0.00222 AFIX 43 H40 2 0.661207 -0.104773 0.171715 11.00000 -1.20000 AFIX 0 C41 1 0.745795 -0.270970 0.072141 11.00000 0.09563 0.05173 = 0.10005 0.01115 0.03055 0.01037 AFIX 43 H41 2 0.774885 -0.343582 0.063957 11.00000 -1.20000 AFIX 0 C42 1 0.734272 -0.206181 0.028916 11.00000 0.10679 0.05668 = 0.07000 -0.00302 0.03256 -0.00444 AFIX 43 H42 2 0.752303 -0.234779 -0.007441 11.00000 -1.20000 AFIX 0 C43 1 0.695367 -0.098281 0.041359 11.00000 0.08908 0.05346 = 0.04899 0.00662 0.01513 -0.01104 AFIX 43 H43 2 0.686601 -0.052343 0.013306 11.00000 -1.20000 AFIX 0 C44 1 0.635954 0.059156 0.113495 11.00000 0.06982 0.05184 = 0.04905 0.00359 0.01255 -0.00448 N1 3 0.713175 0.474586 0.167771 11.00000 0.06452 0.03886 = 0.04661 0.01158 0.01705 0.00842 N2 3 0.634506 0.325126 0.108849 11.00000 0.10026 0.04447 = 0.05835 0.00587 0.01674 0.00333 N3 3 0.204850 0.105704 0.166395 11.00000 0.06533 0.03771 = 0.04612 0.01299 0.01533 -0.00070 N4 3 0.129518 0.227910 0.109269 11.00000 0.10288 0.04828 = 0.06021 0.02122 0.01642 0.00183 C36 1 0.230574 0.717368 0.030228 11.00000 0.10090 0.06175 = 0.06899 0.03182 0.02837 0.01238 AFIX 43 H36 2 0.245651 0.726647 -0.006513 11.00000 -1.20000 AFIX 0 N6 3 0.717971 -0.236170 0.124662 11.00000 0.10748 0.06294 = 0.07868 0.02742 0.02120 0.01401 C12 1 0.625670 0.377518 0.312112 11.00000 0.04454 0.05060 = 0.05874 0.02319 0.02006 0.00507 AFIX 23 H12A 2 0.522364 0.359310 0.285201 11.00000 -1.20000 H12B 2 0.599337 0.428649 0.343669 11.00000 -1.20000 AFIX 0 O2 4 0.243841 0.209355 0.285134 11.00000 0.04762 0.03518 = 0.05458 0.00916 0.01967 -0.00096 O3 4 0.147322 0.486677 0.166985 11.00000 0.13088 0.07115 = 0.05253 0.02280 0.03182 0.00904 O4 4 0.114215 0.416436 0.075165 11.00000 0.12392 0.04591 = 0.05238 0.01614 0.00558 -0.00082 AFIX 148 H4 2 0.126367 0.347944 0.090119 11.00000 -1.50000 AFIX 0 O5 4 0.616501 0.118601 0.072145 11.00000 0.11608 0.04843 = 0.05289 0.00982 0.00654 0.00335 AFIX 148 H5A 2 0.619838 0.205555 0.089855 11.00000 -1.50000 AFIX 0 O6 4 0.632042 0.094633 0.162714 11.00000 0.15681 0.06710 = 0.05891 0.00354 0.04644 0.00649 S1 5 0.823614 0.139041 0.399724 11.00000 0.07151 0.06716 = 0.08324 0.04539 0.02181 0.01196 S2 5 0.340040 0.543196 0.410758 11.00000 0.07986 0.05871 = 0.08929 -0.01661 0.02636 -0.00494 CL1 6 0.519801 0.750057 0.259597 11.00000 0.07343 0.05812 = 0.05891 0.02349 0.00665 0.01949 CL2 6 0.848103 0.887400 0.469788 11.00000 0.11021 0.05990 = 0.06576 -0.00704 0.00719 -0.00263 CL3 6 0.769180 0.368980 0.445957 11.00000 0.11512 0.08893 = 0.05017 0.00581 0.01772 0.00807 CL4 6 0.003706 -0.127204 0.253749 11.00000 0.06734 0.04947 = 0.05802 0.00422 0.00664 -0.01279 CL5 6 0.342675 -0.173280 0.459866 11.00000 0.11144 0.06234 = 0.05776 0.02837 0.01010 -0.00411 CL6 6 0.269620 0.331166 0.448676 11.00000 0.12711 0.11097 = 0.06590 0.03504 0.03043 0.00945 HKLF 4 REM SIR2011 run in space group P -1 REM wR2 = 0.2019, GooF = S = 1.086, Restrained GooF = 1.086 for all data REM R1 = 0.0730 for 7791 Fo > 4sig(Fo) and 0.0813 for all 8855 data REM 582 parameters refined using 0 restraints END WGHT 0.1321 0.5406 REM Highest difference peak 0.814, deepest hole -0.798, 1-sigma level 0.147 Q1 1 0.2835 0.4099 0.4506 11.00000 0.05 0.81 Q2 1 0.6333 -0.0577 0.1010 11.00000 0.05 0.59 Q3 1 0.8287 0.7509 0.4771 11.00000 0.05 0.55 Q4 1 0.6982 0.6958 0.3209 11.00000 0.05 0.51 Q5 1 0.5157 0.8509 0.2603 11.00000 0.05 0.50 ; _shelx_res_checksum 76385 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 0.7394(3) 0.62138(19) 0.31824(10) 0.0428(5) Uani 1 1 d . . . . . C2 C 0.6629(3) 0.72309(19) 0.31855(10) 0.0445(5) Uani 1 1 d . . . . . C3 C 0.6957(3) 0.8047(2) 0.36434(11) 0.0502(6) Uani 1 1 d . . . . . H3 H 0.643463 0.871717 0.363391 0.060 Uiso 1 1 calc R U . . . C4 C 0.8085(3) 0.7850(2) 0.41194(11) 0.0523(6) Uani 1 1 d . . . . . C5 C 0.8882(3) 0.6866(2) 0.41329(11) 0.0522(6) Uani 1 1 d . . . . . H5 H 0.964216 0.674326 0.445249 0.063 Uiso 1 1 calc R U . . . C6 C 0.8540(3) 0.6063(2) 0.36675(10) 0.0469(5) Uani 1 1 d . . . . . H6 H 0.908836 0.540251 0.367702 0.056 Uiso 1 1 calc R U . . . C7 C 0.6979(3) 0.53000(18) 0.26897(10) 0.0425(5) Uani 1 1 d . . . . . H7 H 0.575689 0.526951 0.255705 0.051 Uiso 1 1 calc R U . . . C8 C 0.7884(3) 0.5468(2) 0.21908(10) 0.0482(5) Uani 1 1 d . . . . . H8A H 0.779859 0.622501 0.212095 0.058 Uiso 1 1 calc R U . . . H8B H 0.907207 0.531416 0.228602 0.058 Uiso 1 1 calc R U . . . C9 C 0.7345(4) 0.3668(2) 0.15585(12) 0.0646(7) Uani 1 1 d . . . . . H9 H 0.810264 0.326749 0.177923 0.078 Uiso 1 1 calc R U . . . C10 C 0.5452(4) 0.4098(3) 0.08993(14) 0.0710(8) Uani 1 1 d . . . . . H10 H 0.464165 0.404606 0.057205 0.085 Uiso 1 1 calc R U . . . C11 C 0.5919(4) 0.5024(2) 0.12587(13) 0.0636(7) Uani 1 1 d . . . . . H11 H 0.549755 0.571779 0.122708 0.076 Uiso 1 1 calc R U . . . O1 O 0.7482(2) 0.42648(13) 0.28479(7) 0.0442(4) Uani 1 1 d . . . . . C13 C 0.7562(3) 0.2672(2) 0.38872(11) 0.0523(6) Uani 1 1 d . . . . . C14 C 0.6967(3) 0.2760(2) 0.33347(10) 0.0443(5) Uani 1 1 d . . . . . C15 C 0.7075(3) 0.1747(2) 0.29874(12) 0.0533(6) Uani 1 1 d . . . . . H15 H 0.673900 0.164020 0.259407 0.064 Uiso 1 1 calc R U . . . C16 C 0.7722(4) 0.0950(2) 0.32906(15) 0.0655(8) Uani 1 1 d . . . . . H16 H 0.786696 0.023671 0.312737 0.079 Uiso 1 1 calc R U . . . C17 C 0.2295(3) 0.02861(18) 0.31505(10) 0.0419(5) Uani 1 1 d . . . . . C18 C 0.1501(3) -0.07360(18) 0.31312(10) 0.0425(5) Uani 1 1 d . . . . . C19 C 0.1834(3) -0.13568(19) 0.35740(11) 0.0488(6) Uani 1 1 d . . . . . H19 H 0.128593 -0.203207 0.355390 0.059 Uiso 1 1 calc R U . . . C20 C 0.2991(3) -0.0956(2) 0.40434(11) 0.0512(6) Uani 1 1 d . . . . . C21 C 0.3826(3) 0.0047(2) 0.40785(11) 0.0524(6) Uani 1 1 d . . . . . H21 H 0.460970 0.030942 0.439834 0.063 Uiso 1 1 calc R U . . . C22 C 0.3473(3) 0.0644(2) 0.36320(10) 0.0475(5) Uani 1 1 d . . . . . H22 H 0.404342 0.131239 0.365259 0.057 Uiso 1 1 calc R U . . . C23 C 0.1889(3) 0.09777(18) 0.26689(10) 0.0430(5) Uani 1 1 d . . . . . H23 H 0.066547 0.094719 0.253777 0.052 Uiso 1 1 calc R U . . . C24 C 0.2780(3) 0.0577(2) 0.21701(10) 0.0477(5) Uani 1 1 d . . . . . H24A H 0.397288 0.077898 0.226832 0.057 Uiso 1 1 calc R U . . . H24B H 0.267353 -0.021487 0.208983 0.057 Uiso 1 1 calc R U . . . C25 C 0.2272(5) 0.2084(2) 0.15603(13) 0.0678(8) Uani 1 1 d . . . . . H25 H 0.302709 0.259641 0.179093 0.081 Uiso 1 1 calc R U . . . C26 C 0.0409(4) 0.1325(3) 0.08817(14) 0.0692(8) Uani 1 1 d . . . . . H26 H -0.037893 0.121149 0.054842 0.083 Uiso 1 1 calc R U . . . C27 C 0.0857(4) 0.0572(2) 0.12345(13) 0.0611(7) Uani 1 1 d . . . . . H27 H 0.043105 -0.014341 0.119134 0.073 Uiso 1 1 calc R U . . . C28 C 0.1249(3) 0.2720(2) 0.31378(13) 0.0538(6) Uani 1 1 d . . . . . H28A H 0.093998 0.234069 0.343724 0.065 Uiso 1 1 calc R U . . . H28B H 0.023341 0.280780 0.286975 0.065 Uiso 1 1 calc R U . . . C29 C 0.2637(4) 0.4111(2) 0.39468(12) 0.0583(6) Uani 1 1 d . . . . . C30 C 0.2024(3) 0.3812(2) 0.33868(11) 0.0463(5) Uani 1 1 d . . . . . C31 C 0.2200(3) 0.4697(2) 0.30741(13) 0.0557(6) Uani 1 1 d . . . . . H31 H 0.186846 0.465701 0.268199 0.067 Uiso 1 1 calc R U . . . C32 C 0.2910(4) 0.5611(2) 0.34143(17) 0.0728(9) Uani 1 1 d . . . . . H32 H 0.310461 0.626619 0.327915 0.087 Uiso 1 1 calc R U . . . C33 C 0.1744(3) 0.6048(2) 0.09850(11) 0.0508(6) Uani 1 1 d . . . . . C37 C 0.1924(4) 0.6152(2) 0.04316(12) 0.0630(7) Uani 1 1 d . . . . . H37 H 0.179091 0.554436 0.015136 0.076 Uiso 1 1 calc R U . . . C35 C 0.2457(5) 0.8045(3) 0.07240(17) 0.0797(9) Uani 1 1 d . . . . . H35 H 0.272198 0.872922 0.063236 0.096 Uiso 1 1 calc R U . . . N5 N 0.2251(4) 0.7979(2) 0.12577(14) 0.0811(8) Uani 1 1 d . . . . . C34 C 0.1909(4) 0.6986(3) 0.13746(13) 0.0652(7) Uani 1 1 d . . . . . H34 H 0.177054 0.691887 0.174629 0.078 Uiso 1 1 calc R U . . . C38 C 0.1416(4) 0.4965(2) 0.11682(11) 0.0559(6) Uani 1 1 d . . . . . C39 C 0.6694(3) -0.0585(2) 0.09556(11) 0.0515(6) Uani 1 1 d . . . . . C40 C 0.6808(4) -0.1311(3) 0.13524(13) 0.0645(7) Uani 1 1 d . . . . . H40 H 0.661207 -0.104773 0.171715 0.077 Uiso 1 1 calc R U . . . C41 C 0.7458(5) -0.2710(3) 0.07214(18) 0.0807(10) Uani 1 1 d . . . . . H41 H 0.774885 -0.343582 0.063957 0.097 Uiso 1 1 calc R U . . . C42 C 0.7343(5) -0.2062(3) 0.02892(15) 0.0769(9) Uani 1 1 d . . . . . H42 H 0.752303 -0.234779 -0.007441 0.092 Uiso 1 1 calc R U . . . C43 C 0.6954(4) -0.0983(2) 0.04136(12) 0.0635(7) Uani 1 1 d . . . . . H43 H 0.686601 -0.052343 0.013306 0.076 Uiso 1 1 calc R U . . . C44 C 0.6360(4) 0.0592(2) 0.11350(11) 0.0569(6) Uani 1 1 d . . . . . N1 N 0.7132(3) 0.47459(16) 0.16777(9) 0.0485(5) Uani 1 1 d . . . . . N2 N 0.6345(4) 0.3251(2) 0.10885(11) 0.0674(7) Uani 1 1 d . . . . . N3 N 0.2048(3) 0.10570(16) 0.16639(9) 0.0484(5) Uani 1 1 d . . . . . N4 N 0.1295(4) 0.2279(2) 0.10927(11) 0.0688(7) Uani 1 1 d . . . . . C36 C 0.2306(5) 0.7174(3) 0.03023(15) 0.0734(9) Uani 1 1 d . . . . . H36 H 0.245651 0.726647 -0.006513 0.088 Uiso 1 1 calc R U . . . N6 N 0.7180(4) -0.2362(2) 0.12466(13) 0.0807(8) Uani 1 1 d . . . . . C12 C 0.6257(3) 0.3775(2) 0.31211(11) 0.0485(5) Uani 1 1 d . . . . . H12A H 0.522364 0.359310 0.285201 0.058 Uiso 1 1 calc R U . . . H12B H 0.599337 0.428649 0.343669 0.058 Uiso 1 1 calc R U . . . O2 O 0.24384(19) 0.20935(12) 0.28513(7) 0.0443(4) Uani 1 1 d . . . . . O3 O 0.1473(4) 0.4867(2) 0.16699(9) 0.0816(7) Uani 1 1 d . . . . . O4 O 0.1142(3) 0.41644(17) 0.07517(9) 0.0742(6) Uani 1 1 d . . . . . H4 H 0.126(6) 0.348(4) 0.0901(8) 0.111 Uiso 1 1 calc R U . . . O5 O 0.6165(3) 0.11860(18) 0.07214(9) 0.0730(6) Uani 1 1 d . . . . . H5A H 0.620(6) 0.206(4) 0.0899(8) 0.109 Uiso 1 1 calc R U . . . O6 O 0.6320(4) 0.0946(2) 0.16271(10) 0.0915(8) Uani 1 1 d . . . . . S1 S 0.82361(10) 0.13904(7) 0.39972(4) 0.0697(3) Uani 1 1 d . . . . . S2 S 0.34004(11) 0.54320(7) 0.41076(4) 0.0770(3) Uani 1 1 d . . . . . Cl1 Cl 0.51980(9) 0.75006(6) 0.25960(3) 0.0624(2) Uani 1 1 d . . . . . Cl2 Cl 0.84810(13) 0.88740(7) 0.46979(4) 0.0809(3) Uani 1 1 d . . . . . Cl3 Cl 0.76918(13) 0.36898(8) 0.44596(3) 0.0846(3) Uani 1 1 d . . . . . Cl4 Cl 0.00371(9) -0.12720(5) 0.25375(3) 0.0590(2) Uani 1 1 d . . . . . Cl5 Cl 0.34267(12) -0.17328(7) 0.45987(3) 0.0758(3) Uani 1 1 d . . . . . Cl6 Cl 0.26962(15) 0.33117(10) 0.44868(4) 0.0976(3) 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 0.0471(11) 0.0410(11) 0.0458(11) 0.0153(9) 0.0163(9) 0.0053(9) C2 0.0493(12) 0.0411(12) 0.0492(12) 0.0169(9) 0.0167(9) 0.0072(10) C3 0.0610(14) 0.0387(12) 0.0571(14) 0.0138(10) 0.0225(11) 0.0080(10) C4 0.0633(14) 0.0452(13) 0.0517(13) 0.0073(10) 0.0186(11) -0.0024(11) C5 0.0556(13) 0.0540(14) 0.0486(13) 0.0143(11) 0.0070(10) 0.0019(11) C6 0.0494(12) 0.0442(12) 0.0508(12) 0.0153(10) 0.0116(10) 0.0094(10) C7 0.0479(11) 0.0384(11) 0.0458(11) 0.0135(9) 0.0151(9) 0.0064(9) C8 0.0578(13) 0.0456(12) 0.0460(12) 0.0118(10) 0.0184(10) 0.0029(10) C9 0.096(2) 0.0446(14) 0.0545(15) 0.0101(11) 0.0138(14) 0.0203(14) C10 0.086(2) 0.0598(17) 0.0623(17) 0.0040(14) 0.0019(15) 0.0044(15) C11 0.0794(18) 0.0480(14) 0.0626(16) 0.0133(12) 0.0035(13) 0.0133(13) O1 0.0494(8) 0.0384(8) 0.0522(9) 0.0177(7) 0.0207(7) 0.0072(7) C13 0.0562(14) 0.0542(14) 0.0532(13) 0.0206(11) 0.0179(10) 0.0050(11) C14 0.0430(11) 0.0449(12) 0.0510(12) 0.0164(10) 0.0175(9) 0.0006(9) C15 0.0511(13) 0.0509(14) 0.0617(14) 0.0077(11) 0.0211(11) -0.0061(11) C16 0.0630(16) 0.0431(13) 0.100(2) 0.0177(14) 0.0364(15) 0.0021(12) C17 0.0459(11) 0.0356(11) 0.0479(12) 0.0091(9) 0.0161(9) 0.0016(9) C18 0.0470(11) 0.0365(11) 0.0467(11) 0.0065(9) 0.0154(9) 0.0004(9) C19 0.0618(14) 0.0344(11) 0.0561(13) 0.0095(10) 0.0247(11) -0.0005(10) C20 0.0659(15) 0.0454(13) 0.0474(12) 0.0128(10) 0.0187(11) 0.0034(11) C21 0.0612(14) 0.0486(13) 0.0480(12) 0.0091(10) 0.0088(10) -0.0011(11) C22 0.0509(12) 0.0405(12) 0.0536(13) 0.0101(10) 0.0130(10) -0.0047(10) C23 0.0475(11) 0.0358(11) 0.0488(12) 0.0100(9) 0.0137(9) -0.0021(9) C24 0.0570(13) 0.0422(12) 0.0478(12) 0.0127(10) 0.0148(10) 0.0039(10) C25 0.101(2) 0.0482(15) 0.0563(15) 0.0156(12) 0.0133(15) -0.0163(15) C26 0.084(2) 0.0587(17) 0.0647(17) 0.0218(14) 0.0012(14) -0.0018(15) C27 0.0740(17) 0.0439(13) 0.0650(16) 0.0157(12) 0.0038(13) -0.0056(12) C28 0.0497(13) 0.0418(12) 0.0733(16) 0.0042(11) 0.0237(11) 0.0010(10) C29 0.0622(15) 0.0553(15) 0.0619(15) 0.0076(12) 0.0236(12) 0.0053(12) C30 0.0450(11) 0.0407(12) 0.0587(13) 0.0096(10) 0.0216(10) 0.0069(9) C31 0.0536(13) 0.0515(14) 0.0703(16) 0.0197(12) 0.0255(12) 0.0136(11) C32 0.0631(17) 0.0371(13) 0.131(3) 0.0238(16) 0.0438(18) 0.0089(12) C33 0.0608(14) 0.0479(13) 0.0468(12) 0.0147(10) 0.0108(10) 0.0081(11) C37 0.092(2) 0.0522(15) 0.0488(14) 0.0152(11) 0.0156(13) 0.0134(14) C35 0.097(2) 0.0554(18) 0.095(2) 0.0257(17) 0.0281(19) -0.0019(17) N5 0.112(2) 0.0506(14) 0.0817(19) 0.0034(13) 0.0238(16) -0.0054(14) C34 0.087(2) 0.0568(16) 0.0536(15) 0.0075(12) 0.0177(13) 0.0026(15) C38 0.0716(16) 0.0537(15) 0.0468(13) 0.0178(11) 0.0138(11) 0.0087(12) C39 0.0584(14) 0.0484(13) 0.0477(12) 0.0071(10) 0.0086(10) -0.0038(11) C40 0.0827(19) 0.0599(16) 0.0543(15) 0.0155(13) 0.0147(13) 0.0022(14) C41 0.096(2) 0.0517(17) 0.100(3) 0.0111(17) 0.031(2) 0.0104(16) C42 0.107(3) 0.0567(17) 0.0700(19) -0.0030(15) 0.0326(18) -0.0044(17) C43 0.089(2) 0.0535(15) 0.0490(14) 0.0066(11) 0.0151(13) -0.0110(14) C44 0.0698(16) 0.0518(14) 0.0490(13) 0.0036(11) 0.0126(11) -0.0045(12) N1 0.0645(12) 0.0389(10) 0.0466(10) 0.0116(8) 0.0170(9) 0.0084(9) N2 0.1003(19) 0.0445(12) 0.0583(13) 0.0059(10) 0.0167(12) 0.0033(12) N3 0.0653(12) 0.0377(10) 0.0461(10) 0.0130(8) 0.0153(9) -0.0007(9) N4 0.1029(19) 0.0483(13) 0.0602(14) 0.0212(11) 0.0164(13) 0.0018(13) C36 0.101(2) 0.0617(18) 0.0690(18) 0.0318(15) 0.0284(17) 0.0124(17) N6 0.107(2) 0.0629(16) 0.0787(18) 0.0274(14) 0.0212(16) 0.0140(15) C12 0.0445(12) 0.0506(13) 0.0587(14) 0.0232(11) 0.0201(10) 0.0051(10) O2 0.0476(8) 0.0352(8) 0.0546(9) 0.0092(7) 0.0197(7) -0.0010(6) O3 0.131(2) 0.0712(14) 0.0525(11) 0.0228(10) 0.0318(12) 0.0090(13) O4 0.1239(19) 0.0459(10) 0.0524(11) 0.0161(9) 0.0056(11) -0.0008(11) O5 0.1161(18) 0.0484(11) 0.0529(11) 0.0098(9) 0.0065(11) 0.0034(11) O6 0.157(2) 0.0671(14) 0.0589(13) 0.0035(11) 0.0464(14) 0.0065(15) S1 0.0715(5) 0.0672(5) 0.0832(5) 0.0454(4) 0.0218(4) 0.0120(4) S2 0.0799(5) 0.0587(5) 0.0893(6) -0.0166(4) 0.0264(4) -0.0049(4) Cl1 0.0734(4) 0.0581(4) 0.0589(4) 0.0235(3) 0.0067(3) 0.0195(3) Cl2 0.1102(7) 0.0599(5) 0.0658(5) -0.0070(3) 0.0072(4) -0.0026(4) Cl3 0.1151(7) 0.0889(6) 0.0502(4) 0.0058(4) 0.0177(4) 0.0081(5) Cl4 0.0673(4) 0.0495(4) 0.0580(4) 0.0042(3) 0.0066(3) -0.0128(3) Cl5 0.1114(6) 0.0623(4) 0.0578(4) 0.0284(3) 0.0101(4) -0.0041(4) Cl6 0.1271(8) 0.1110(8) 0.0659(5) 0.0350(5) 0.0304(5) 0.0094(6) 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 116.7(2) . . ? C6 C1 C7 120.8(2) . . ? C2 C1 C7 122.5(2) . . ? C3 C2 C1 122.4(2) . . ? C3 C2 Cl1 117.53(19) . . ? C1 C2 Cl1 120.03(19) . . ? C2 C3 C4 118.6(2) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 121.0(2) . . ? C5 C4 Cl2 120.5(2) . . ? C3 C4 Cl2 118.5(2) . . ? C4 C5 C6 119.3(2) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C1 122.0(2) . . ? C5 C6 H6 119.0 . . ? C1 C6 H6 119.0 . . ? O1 C7 C1 112.03(18) . . ? O1 C7 C8 105.98(18) . . ? C1 C7 C8 112.13(18) . . ? O1 C7 H7 108.9 . . ? C1 C7 H7 108.9 . . ? C8 C7 H7 108.9 . . ? N1 C8 C7 110.28(19) . . ? 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 111.2(3) . . ? N2 C9 H9 124.4 . . ? N1 C9 H9 124.4 . . ? C11 C10 N2 109.5(3) . . ? C11 C10 H10 125.3 . . ? N2 C10 H10 125.3 . . ? C10 C11 N1 106.6(3) . . ? C10 C11 H11 126.7 . . ? N1 C11 H11 126.7 . . ? C7 O1 C12 112.22(17) . . ? C14 C13 S1 113.7(2) . . ? C14 C13 Cl3 127.0(2) . . ? S1 C13 Cl3 119.35(15) . . ? C13 C14 C15 110.4(2) . . ? C13 C14 C12 124.9(2) . . ? C15 C14 C12 124.7(2) . . ? C16 C15 C14 112.7(3) . . ? C16 C15 H15 123.7 . . ? C14 C15 H15 123.7 . . ? C15 C16 S1 113.0(2) . . ? C15 C16 H16 123.5 . . ? S1 C16 H16 123.5 . . ? C22 C17 C18 116.9(2) . . ? C22 C17 C23 121.3(2) . . ? C18 C17 C23 121.8(2) . . ? C19 C18 C17 122.0(2) . . ? C19 C18 Cl4 117.59(17) . . ? C17 C18 Cl4 120.37(18) . . ? C20 C19 C18 118.6(2) . . ? C20 C19 H19 120.7 . . ? C18 C19 H19 120.7 . . ? C19 C20 C21 121.4(2) . . ? C19 C20 Cl5 118.95(19) . . ? C21 C20 Cl5 119.7(2) . . ? C22 C21 C20 118.7(2) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? C21 C22 C17 122.3(2) . . ? C21 C22 H22 118.9 . . ? C17 C22 H22 118.9 . . ? O2 C23 C24 106.32(17) . . ? O2 C23 C17 111.28(18) . . ? C24 C23 C17 111.63(19) . . ? O2 C23 H23 109.2 . . ? C24 C23 H23 109.2 . . ? C17 C23 H23 109.2 . . ? N3 C24 C23 110.5(2) . . ? N3 C24 H24A 109.6 . . ? C23 C24 H24A 109.6 . . ? N3 C24 H24B 109.6 . . ? C23 C24 H24B 109.6 . . ? H24A C24 H24B 108.1 . . ? N4 C25 N3 111.6(3) . . ? N4 C25 H25 124.2 . . ? N3 C25 H25 124.2 . . ? C27 C26 N4 109.0(3) . . ? C27 C26 H26 125.5 . . ? N4 C26 H26 125.5 . . ? C26 C27 N3 107.1(2) . . ? C26 C27 H27 126.5 . . ? N3 C27 H27 126.5 . . ? O2 C28 C30 109.21(19) . . ? O2 C28 H28A 109.8 . . ? C30 C28 H28A 109.8 . . ? O2 C28 H28B 109.8 . . ? C30 C28 H28B 109.8 . . ? H28A C28 H28B 108.3 . . ? C30 C29 S2 113.9(2) . . ? C30 C29 Cl6 127.0(2) . . ? S2 C29 Cl6 119.08(18) . . ? C29 C30 C31 110.4(2) . . ? C29 C30 C28 124.7(2) . . ? C31 C30 C28 124.9(3) . . ? C32 C31 C30 112.3(3) . . ? C32 C31 H31 123.9 . . ? C30 C31 H31 123.9 . . ? C31 C32 S2 113.1(2) . . ? C31 C32 H32 123.5 . . ? S2 C32 H32 123.5 . . ? C34 C33 C37 117.6(3) . . ? C34 C33 C38 120.2(2) . . ? C37 C33 C38 122.2(2) . . ? C36 C37 C33 118.7(3) . . ? C36 C37 H37 120.7 . . ? C33 C37 H37 120.7 . . ? N5 C35 C36 124.2(3) . . ? N5 C35 H35 117.9 . . ? C36 C35 H35 117.9 . . ? C34 N5 C35 116.1(3) . . ? N5 C34 C33 124.7(3) . . ? N5 C34 H34 117.7 . . ? C33 C34 H34 117.7 . . ? O3 C38 O4 124.8(3) . . ? O3 C38 C33 121.3(3) . . ? O4 C38 C33 113.9(2) . . ? C43 C39 C40 117.7(3) . . ? C43 C39 C44 123.0(2) . . ? C40 C39 C44 119.3(2) . . ? N6 C40 C39 124.3(3) . . ? N6 C40 H40 117.8 . . ? C39 C40 H40 117.8 . . ? N6 C41 C42 124.2(3) . . ? N6 C41 H41 117.9 . . ? C42 C41 H41 117.9 . . ? C43 C42 C41 117.9(3) . . ? C43 C42 H42 121.1 . . ? C41 C42 H42 121.1 . . ? C42 C43 C39 119.6(3) . . ? C42 C43 H43 120.2 . . ? C39 C43 H43 120.2 . . ? O6 C44 O5 124.0(3) . . ? O6 C44 C39 121.8(3) . . ? O5 C44 C39 114.2(2) . . ? C9 N1 C11 106.8(2) . . ? C9 N1 C8 127.1(2) . . ? C11 N1 C8 125.7(2) . . ? C9 N2 C10 106.0(2) . . ? C25 N3 C27 106.5(2) . . ? C25 N3 C24 127.3(2) . . ? C27 N3 C24 125.9(2) . . ? C25 N4 C26 105.8(2) . . ? C35 C36 C37 118.7(3) . . ? C35 C36 H36 120.7 . . ? C37 C36 H36 120.7 . . ? C41 N6 C40 116.2(3) . . ? O1 C12 C14 108.84(18) . . ? O1 C12 H12A 109.9 . . ? C14 C12 H12A 109.9 . . ? O1 C12 H12B 109.9 . . ? C14 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? C23 O2 C28 112.87(17) . . ? C38 O4 H4 109.5 . . ? C44 O5 H5A 109.5 . . ? C16 S1 C13 90.21(14) . . ? C32 S2 C29 90.34(15) . . ? 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 1.397(3) . ? C1 C2 1.399(3) . ? C1 C7 1.513(3) . ? C2 C3 1.377(4) . ? C2 Cl1 1.743(2) . ? C3 C4 1.388(4) . ? C3 H3 0.9300 . ? C4 C5 1.377(4) . ? C4 Cl2 1.734(3) . ? C5 C6 1.379(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.422(3) . ? C7 C8 1.531(3) . ? C7 H7 0.9800 . ? C8 N1 1.461(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.315(4) . ? C9 N1 1.339(3) . ? C9 H9 0.9300 . ? C10 C11 1.347(4) . ? C10 N2 1.357(4) . ? C10 H10 0.9300 . ? C11 N1 1.363(4) . ? C11 H11 0.9300 . ? O1 C12 1.436(3) . ? C13 C14 1.353(4) . ? C13 S1 1.713(3) . ? C13 Cl3 1.721(3) . ? C14 C15 1.417(4) . ? C14 C12 1.497(3) . ? C15 C16 1.356(4) . ? C15 H15 0.9300 . ? C16 S1 1.692(4) . ? C16 H16 0.9300 . ? C17 C22 1.389(3) . ? C17 C18 1.399(3) . ? C17 C23 1.521(3) . ? C18 C19 1.383(3) . ? C18 Cl4 1.745(2) . ? C19 C20 1.372(4) . ? C19 H19 0.9300 . ? C20 C21 1.387(4) . ? C20 Cl5 1.734(3) . ? C21 C22 1.373(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 O2 1.430(3) . ? C23 C24 1.520(3) . ? C23 H23 0.9800 . ? C24 N3 1.461(3) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 N4 1.313(4) . ? C25 N3 1.338(3) . ? C25 H25 0.9300 . ? C26 C27 1.350(4) . ? C26 N4 1.362(4) . ? C26 H26 0.9300 . ? C27 N3 1.357(4) . ? C27 H27 0.9300 . ? C28 O2 1.435(3) . ? C28 C30 1.486(3) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.355(4) . ? C29 S2 1.708(3) . ? C29 Cl6 1.723(3) . ? C30 C31 1.422(4) . ? C31 C32 1.362(4) . ? C31 H31 0.9300 . ? C32 S2 1.691(4) . ? C32 H32 0.9300 . ? C33 C34 1.377(4) . ? C33 C37 1.380(4) . ? C33 C38 1.494(4) . ? C37 C36 1.380(4) . ? C37 H37 0.9300 . ? C35 N5 1.329(5) . ? C35 C36 1.364(5) . ? C35 H35 0.9300 . ? N5 C34 1.328(4) . ? C34 H34 0.9300 . ? C38 O3 1.219(3) . ? C38 O4 1.297(3) . ? C39 C43 1.376(4) . ? C39 C40 1.383(4) . ? C39 C44 1.496(4) . ? C40 N6 1.331(4) . ? C40 H40 0.9300 . ? C41 N6 1.330(5) . ? C41 C42 1.383(5) . ? C41 H41 0.9300 . ? C42 C43 1.373(5) . ? C42 H42 0.9300 . ? C43 H43 0.9300 . ? C44 O6 1.208(3) . ? C44 O5 1.300(3) . ? C36 H36 0.9300 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? O4 H4 0.96(5) . ? O5 H5A 1.10(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 -0.9(3) . . . . ? C7 C1 C2 C3 177.4(2) . . . . ? C6 C1 C2 Cl1 179.33(17) . . . . ? C7 C1 C2 Cl1 -2.4(3) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? Cl1 C2 C3 C4 179.60(19) . . . . ? C2 C3 C4 C5 0.9(4) . . . . ? C2 C3 C4 Cl2 -179.41(19) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? Cl2 C4 C5 C6 179.81(19) . . . . ? C4 C5 C6 C1 -0.6(4) . . . . ? C2 C1 C6 C5 1.3(3) . . . . ? C7 C1 C6 C5 -177.0(2) . . . . ? C6 C1 C7 O1 16.4(3) . . . . ? C2 C1 C7 O1 -161.8(2) . . . . ? C6 C1 C7 C8 -102.6(2) . . . . ? C2 C1 C7 C8 79.2(3) . . . . ? O1 C7 C8 N1 72.2(2) . . . . ? C1 C7 C8 N1 -165.3(2) . . . . ? N2 C10 C11 N1 0.2(4) . . . . ? C1 C7 O1 C12 82.8(2) . . . . ? C8 C7 O1 C12 -154.63(19) . . . . ? S1 C13 C14 C15 -0.4(3) . . . . ? Cl3 C13 C14 C15 179.55(19) . . . . ? S1 C13 C14 C12 178.27(18) . . . . ? Cl3 C13 C14 C12 -1.8(4) . . . . ? C13 C14 C15 C16 0.6(3) . . . . ? C12 C14 C15 C16 -178.1(2) . . . . ? C14 C15 C16 S1 -0.6(3) . . . . ? C22 C17 C18 C19 1.5(3) . . . . ? C23 C17 C18 C19 -178.4(2) . . . . ? C22 C17 C18 Cl4 -178.53(17) . . . . ? C23 C17 C18 Cl4 1.6(3) . . . . ? C17 C18 C19 C20 -0.5(4) . . . . ? Cl4 C18 C19 C20 179.50(19) . . . . ? C18 C19 C20 C21 -0.4(4) . . . . ? C18 C19 C20 Cl5 -179.58(18) . . . . ? C19 C20 C21 C22 0.2(4) . . . . ? Cl5 C20 C21 C22 179.4(2) . . . . ? C20 C21 C22 C17 0.9(4) . . . . ? C18 C17 C22 C21 -1.6(4) . . . . ? C23 C17 C22 C21 178.2(2) . . . . ? C22 C17 C23 O2 -17.5(3) . . . . ? C18 C17 C23 O2 162.3(2) . . . . ? C22 C17 C23 C24 101.1(3) . . . . ? C18 C17 C23 C24 -79.1(3) . . . . ? O2 C23 C24 N3 -73.1(2) . . . . ? C17 C23 C24 N3 165.38(18) . . . . ? N4 C26 C27 N3 -0.8(4) . . . . ? S2 C29 C30 C31 0.6(3) . . . . ? Cl6 C29 C30 C31 -179.9(2) . . . . ? S2 C29 C30 C28 -178.34(19) . . . . ? Cl6 C29 C30 C28 1.2(4) . . . . ? O2 C28 C30 C29 -103.5(3) . . . . ? O2 C28 C30 C31 77.7(3) . . . . ? C29 C30 C31 C32 -0.8(3) . . . . ? C28 C30 C31 C32 178.1(2) . . . . ? C30 C31 C32 S2 0.7(3) . . . . ? C34 C33 C37 C36 1.9(5) . . . . ? C38 C33 C37 C36 -176.9(3) . . . . ? C36 C35 N5 C34 1.3(6) . . . . ? C35 N5 C34 C33 -0.6(6) . . . . ? C37 C33 C34 N5 -1.0(5) . . . . ? C38 C33 C34 N5 177.9(3) . . . . ? C34 C33 C38 O3 -8.2(5) . . . . ? C37 C33 C38 O3 170.6(3) . . . . ? C34 C33 C38 O4 174.3(3) . . . . ? C37 C33 C38 O4 -6.9(4) . . . . ? C43 C39 C40 N6 1.2(5) . . . . ? C44 C39 C40 N6 -176.7(3) . . . . ? N6 C41 C42 C43 1.6(6) . . . . ? C41 C42 C43 C39 0.0(5) . . . . ? C40 C39 C43 C42 -1.3(5) . . . . ? C44 C39 C43 C42 176.6(3) . . . . ? C43 C39 C44 O6 -171.7(3) . . . . ? C40 C39 C44 O6 6.1(5) . . . . ? C43 C39 C44 O5 6.6(4) . . . . ? C40 C39 C44 O5 -175.6(3) . . . . ? N2 C9 N1 C11 0.2(4) . . . . ? N2 C9 N1 C8 173.3(2) . . . . ? C10 C11 N1 C9 -0.3(4) . . . . ? C10 C11 N1 C8 -173.5(3) . . . . ? C7 C8 N1 C9 -76.1(3) . . . . ? C7 C8 N1 C11 95.7(3) . . . . ? N1 C9 N2 C10 -0.1(4) . . . . ? C11 C10 N2 C9 -0.1(4) . . . . ? N4 C25 N3 C27 0.1(4) . . . . ? N4 C25 N3 C24 -173.4(2) . . . . ? C26 C27 N3 C25 0.4(4) . . . . ? C26 C27 N3 C24 174.0(3) . . . . ? C23 C24 N3 C25 75.2(3) . . . . ? C23 C24 N3 C27 -97.1(3) . . . . ? N3 C25 N4 C26 -0.6(4) . . . . ? C27 C26 N4 C25 0.9(4) . . . . ? N5 C35 C36 C37 -0.4(6) . . . . ? C33 C37 C36 C35 -1.3(5) . . . . ? C42 C41 N6 C40 -1.6(6) . . . . ? C39 C40 N6 C41 0.2(5) . . . . ? C7 O1 C12 C14 -173.39(19) . . . . ? C13 C14 C12 O1 104.6(3) . . . . ? C15 C14 C12 O1 -76.9(3) . . . . ? C24 C23 O2 C28 155.1(2) . . . . ? C17 C23 O2 C28 -83.2(2) . . . . ? C30 C28 O2 C23 171.6(2) . . . . ? C15 C16 S1 C13 0.3(2) . . . . ? C14 C13 S1 C16 0.1(2) . . . . ? Cl3 C13 S1 C16 -179.87(17) . . . . ? C31 C32 S2 C29 -0.3(2) . . . . ? C30 C29 S2 C32 -0.2(2) . . . . ? Cl6 C29 S2 C32 -179.75(19) . . . . ?