#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:01:35 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288801 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247721.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_7247721 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 '2(C16 H14 Cl3 N2 O S), C2 O4, 4(H2 O)' _chemical_formula_sum 'C34 H36 Cl6 N4 O10 S2' _chemical_formula_weight 937.49 _chemical_name_common 'Tioconazole-oxalate (2:1)salt tetrahydrate' _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-2019/2 _audit_update_record ; 2023-09-21 deposited with the CCDC. 2023-11-14 downloaded from the CCDC. ; _cell_angle_alpha 73.851(2) _cell_angle_beta 78.295(2) _cell_angle_gamma 85.648(2) _cell_formula_units_Z 2 _cell_length_a 7.65410(10) _cell_length_b 15.9993(4) _cell_length_c 17.8133(5) _cell_measurement_reflns_used 18144 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 78.8510 _cell_measurement_theta_min 2.6290 _cell_volume 2051.33(9) _computing_cell_refinement 'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)' _computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100(2) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -48.00 -21.00 0.50 0.43 -- -91.75 45.00 60.00 54 2 \w -102.00 -43.00 0.50 0.43 -- -91.75 77.00 0.00 118 3 \w -48.00 -21.00 0.50 0.43 -- -91.75 45.00 -60.00 54 4 \w -49.00 -24.00 0.50 0.43 -- -91.75 45.00 -90.00 50 5 \w -41.00 26.00 0.50 0.11 -- -47.33 38.00-120.00 134 6 \w -16.00 11.00 0.50 0.11 -- -47.33 19.00-180.00 54 7 \w -39.00 26.00 0.50 0.11 -- -47.33 38.00 0.00 130 8 \w -17.00 20.00 0.50 0.11 -- -47.33 19.00 120.00 74 9 \w -18.00 21.00 0.50 0.11 -- -47.33 19.00 150.00 78 10 \w -74.00 1.00 0.50 0.11 -- -47.33 96.00 61.00 150 11 \w -84.00 -13.00 0.50 0.11 -- -47.33 125.00 90.00 142 12 \w -67.00 -41.00 0.50 0.43 -- -91.75 96.00 61.00 52 13 \w -147.00-122.00 0.50 0.43 -- -91.75 -96.00 -48.00 50 14 \w 43.00 72.00 0.50 0.43 -- 113.25 -61.00 90.00 58 15 \w 44.00 107.00 0.50 0.43 -- 113.25 -77.00 60.00 126 16 \w 82.00 107.00 0.50 0.43 -- 113.25 -77.00 -90.00 50 17 \w 43.00 68.00 0.50 0.43 -- 113.25 -77.00 -90.00 50 18 \w 42.00 73.00 0.50 0.43 -- 113.25 -61.00 60.00 62 19 \w 46.00 72.00 0.50 0.43 -- 113.25 -61.00 150.00 52 20 \w 45.00 72.00 0.50 0.43 -- 113.25 -61.00 0.00 54 21 \w 96.00 176.00 0.50 0.43 -- 113.25 125.00 90.00 160 22 \w 106.00 171.00 0.50 0.43 -- 113.25 96.00 61.00 130 23 \w 43.00 71.00 0.50 0.43 -- 113.25 -61.00-150.00 56 24 \w 42.00 67.00 0.50 0.43 -- 113.25 -61.00-120.00 50 25 \w 51.00 76.00 0.50 0.43 -- 113.25 -95.00-150.00 50 26 \w 62.00 111.00 0.50 0.43 -- 113.25-125.00 -30.00 98 27 \w 66.00 106.00 0.50 0.43 -- 113.25-110.00 40.82 80 28 \w 44.00 111.00 0.50 0.43 -- 113.25-125.00 90.00 134 29 \w 68.00 109.00 0.50 0.43 -- 113.25-115.00 84.49 82 30 \w 45.00 70.00 0.50 0.43 -- 113.25 -95.00 150.00 50 31 \w 81.00 106.00 0.50 0.43 -- 113.25 -95.00 150.00 50 32 \w 49.00 85.00 0.50 0.43 -- 113.25 -95.00 0.00 72 33 \w 68.00 103.00 0.50 0.43 -- 113.25 -96.00 -48.00 70 34 \w 79.00 106.00 0.50 0.43 -- 113.25 -95.00-120.00 54 35 \w 42.00 75.00 0.50 0.43 -- 113.25 -95.00-120.00 66 36 \w 46.00 72.00 0.50 0.43 -- 113.25 -95.00-180.00 52 37 \w 80.00 106.00 0.50 0.43 -- 113.25 -95.00-150.00 52 38 \w 79.00 105.00 0.50 0.43 -- 113.25 -95.00-180.00 52 39 \w 1.00 41.00 0.50 0.11 -- 47.33 -96.00 -48.00 80 40 \w 71.00 96.00 0.50 0.43 -- 113.25 -95.00 90.00 50 41 \w 79.00 105.00 0.50 0.43 -- 113.25 -95.00 120.00 52 42 \w 101.00 156.00 0.50 0.43 -- 113.25 15.00-120.00 110 43 \w 114.00 174.00 0.50 0.43 -- 113.25 45.00-120.00 120 44 \w 101.00 176.00 0.50 0.43 -- 113.25 45.00 -30.00 150 45 \w 127.00 164.00 0.50 0.43 -- 113.25 45.00 -60.00 74 46 \w 98.00 173.00 0.50 0.43 -- 113.25 61.00 0.00 150 47 \w 119.00 177.00 0.50 0.43 -- 113.25 30.00 -90.00 116 48 \w 105.00 150.00 0.50 0.43 -- 113.25 45.00 60.00 90 49 \w 118.00 144.00 0.50 0.43 -- 113.25 45.00 120.00 52 50 \w 97.00 170.00 0.50 0.43 -- 113.25 61.00 150.00 146 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0367903000 _diffrn_orient_matrix_UB_12 0.0356608000 _diffrn_orient_matrix_UB_13 -0.0851559000 _diffrn_orient_matrix_UB_21 0.0131369000 _diffrn_orient_matrix_UB_22 -0.0931258000 _diffrn_orient_matrix_UB_23 -0.0096993000 _diffrn_orient_matrix_UB_31 -0.2018460000 _diffrn_orient_matrix_UB_32 -0.0104474000 _diffrn_orient_matrix_UB_33 0.0326156000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0699 _diffrn_reflns_av_unetI/netI 0.0597 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.975 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 28902 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.975 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 79.808 _diffrn_reflns_theta_min 2.630 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 5.284 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.61561 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_density_diffrn 1.518 _exptl_crystal_description plate _exptl_crystal_F_000 964 _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_min 0.030 _refine_diff_density_max 0.543 _refine_diff_density_min -0.498 _refine_diff_density_rms 0.080 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 555 _refine_ls_number_reflns 8721 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.095 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0492 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0822P)^2^+0.4318P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1362 _refine_ls_wR_factor_ref 0.1414 _reflns_Friedel_coverage 0.000 _reflns_number_gt 7474 _reflns_number_total 8721 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00948c2.cif _cod_data_source_block TCZ_OXAH _cod_depositor_comments 'Adding full bibliography for 7247709--7247724.cif.' _cod_database_code 7247721 _shelx_shelxl_version_number 2019/2 _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 0.505 _shelx_estimated_absorpt_t_max 0.858 _shelx_res_file ; TITL AM230915b in P-1 shelx.res created by SHELXL-2019/2 at 13:34:40 on 18-Sep-2023 CELL 1.54184 7.6541 15.9993 17.8133 73.851 78.295 85.648 ZERR 2.00 0.0001 0.0004 0.0005 0.002 0.002 0.002 LATT 1 SFAC C H CL S N O UNIT 68 72 12 4 8 20 MERG 2 FMAP 2 PLAN 2 SIZE 0.030 0.060 0.150 ACTA BOND $H CONF LIST 4 L.S. 10 TEMP -173.00 WGHT 0.082200 0.431800 FVAR 3.27394 0.52508 C1 1 0.099161 0.042819 0.831309 11.00000 0.03000 0.01916 = 0.04390 -0.00895 0.00153 -0.00021 C2 1 0.160849 -0.012221 0.896452 11.00000 0.03726 0.02313 = 0.03577 -0.01135 0.00389 -0.00073 C3 1 0.062148 -0.081333 0.948413 11.00000 0.06163 0.02283 = 0.03708 -0.01056 0.01582 -0.00371 AFIX 43 H3 2 0.106286 -0.117867 0.992808 11.00000 -1.20000 AFIX 0 C4 1 -0.102064 -0.095592 0.933849 11.00000 0.05394 0.02221 = 0.06491 -0.01825 0.03316 -0.01191 C5 1 -0.166856 -0.043053 0.869152 11.00000 0.03217 0.02914 = 0.09949 -0.02427 0.01220 -0.01047 AFIX 43 H5 2 -0.279344 -0.054136 0.859501 11.00000 -1.20000 AFIX 0 C6 1 -0.066209 0.025874 0.818562 11.00000 0.03133 0.02679 = 0.07297 -0.01148 -0.00580 -0.00167 AFIX 43 H6 2 -0.111048 0.062268 0.774303 11.00000 -1.20000 AFIX 0 C7 1 0.206878 0.117673 0.773475 11.00000 0.02970 0.01773 = 0.04111 -0.00624 -0.00320 -0.00150 AFIX 13 H7 2 0.288999 0.138858 0.800992 11.00000 -1.20000 AFIX 0 C8 1 0.314945 0.089352 0.701973 11.00000 0.02857 0.01904 = 0.04440 -0.00783 0.00068 -0.00225 AFIX 23 H8A 2 0.377466 0.033241 0.720839 11.00000 -1.20000 H8B 2 0.233555 0.080942 0.668120 11.00000 -1.20000 AFIX 0 C9 1 0.411610 0.234096 0.609882 11.00000 0.03079 0.02381 = 0.03782 -0.00523 -0.00354 -0.00098 AFIX 43 H9 2 0.298058 0.255533 0.598424 11.00000 -1.20000 AFIX 0 C10 1 0.697082 0.226257 0.612946 11.00000 0.02749 0.03419 = 0.04618 -0.01198 0.00084 -0.00114 AFIX 43 H10 2 0.818582 0.241625 0.603708 11.00000 -1.20000 AFIX 0 C11 1 0.625012 0.149746 0.657825 11.00000 0.02463 0.02946 = 0.04627 -0.00870 -0.00076 0.00153 AFIX 43 H11 2 0.686427 0.100993 0.685918 11.00000 -1.20000 AFIX 0 C12 1 0.023405 0.239419 0.793954 11.00000 0.04175 0.02338 = 0.03912 -0.01253 -0.00536 0.00288 AFIX 23 H12A 2 0.120948 0.269230 0.804447 11.00000 -1.20000 H12B 2 -0.038775 0.202096 0.845203 11.00000 -1.20000 AFIX 0 C13 1 -0.285153 0.300961 0.777543 11.00000 0.03360 0.03066 = 0.04525 -0.01853 0.00151 -0.00332 C14 1 -0.103900 0.304587 0.756035 11.00000 0.03637 0.02342 = 0.03539 -0.01391 -0.00141 -0.00109 C15 1 -0.052794 0.379622 0.691303 11.00000 0.04314 0.02580 = 0.03437 -0.01381 -0.00362 -0.00374 AFIX 43 H15 2 0.067917 0.393217 0.667263 11.00000 -1.20000 AFIX 0 C16 1 -0.193457 0.429652 0.667446 11.00000 0.05991 0.03165 = 0.03751 -0.01438 -0.01615 0.00526 AFIX 43 H16 2 -0.182320 0.481895 0.625460 11.00000 -1.20000 AFIX 0 C17 1 -0.162975 0.572323 0.800895 11.00000 0.02625 0.02230 = 0.02129 -0.00752 -0.00641 -0.00055 C18 1 -0.122153 0.487822 0.842322 11.00000 0.02608 0.02309 = 0.02547 -0.00761 -0.00955 -0.00136 C19 1 -0.252153 0.430657 0.890912 11.00000 0.03085 0.02210 = 0.02780 -0.00481 -0.01072 -0.00495 AFIX 43 H19 2 -0.221486 0.373138 0.918154 11.00000 -1.20000 AFIX 0 C20 1 -0.428946 0.460220 0.898498 11.00000 0.02763 0.02577 = 0.02509 -0.00609 -0.00396 -0.00642 C21 1 -0.475902 0.543070 0.857713 11.00000 0.02345 0.02700 = 0.03015 -0.01054 -0.00597 -0.00129 AFIX 43 H21 2 -0.597376 0.561967 0.862799 11.00000 -1.20000 AFIX 0 C22 1 -0.342007 0.598050 0.809206 11.00000 0.02767 0.02164 = 0.02856 -0.00763 -0.00892 0.00088 AFIX 43 H22 2 -0.373535 0.654945 0.780833 11.00000 -1.20000 AFIX 0 C23 1 -0.017317 0.635633 0.752830 11.00000 0.02616 0.01914 = 0.02394 -0.00582 -0.00623 -0.00126 AFIX 13 H23 2 0.077295 0.631655 0.785081 11.00000 -1.20000 AFIX 0 C24 1 0.069126 0.618101 0.673360 11.00000 0.02771 0.02809 = 0.02558 -0.00868 -0.00262 -0.00668 AFIX 23 H24A 2 0.096537 0.555139 0.681128 11.00000 -1.20000 H24B 2 -0.013911 0.635953 0.635479 11.00000 -1.20000 AFIX 0 C25 1 0.245120 0.751936 0.602731 11.00000 0.02826 0.02620 = 0.02435 -0.00265 -0.00347 -0.00133 AFIX 43 H25 2 0.148988 0.788925 0.586274 11.00000 -1.20000 AFIX 0 C26 1 0.512063 0.704546 0.623810 11.00000 0.02436 0.04155 = 0.04164 0.00236 -0.00416 -0.00095 AFIX 43 H26 2 0.636243 0.703334 0.624033 11.00000 -1.20000 AFIX 0 C27 1 0.401071 0.637007 0.655422 11.00000 0.02731 0.03273 = 0.04016 -0.00118 -0.00615 0.00444 AFIX 43 H27 2 0.431954 0.579369 0.682274 11.00000 -1.20000 AFIX 0 C28 1 -0.099341 0.764509 0.796548 11.00000 0.02901 0.02355 = 0.02852 -0.00893 -0.00449 -0.00004 AFIX 23 H28A 2 -0.175420 0.728953 0.844963 11.00000 -1.20000 H28B 2 -0.158826 0.822153 0.780958 11.00000 -1.20000 AFIX 0 C29 1 0.144263 0.725080 0.878452 11.00000 0.02729 0.02316 = 0.02672 -0.00978 -0.00290 -0.00208 C30 1 0.078916 0.776017 0.815005 11.00000 0.02690 0.01951 = 0.02808 -0.00915 -0.00241 -0.00121 C31 1 0.205083 0.840110 0.767450 11.00000 0.03608 0.02028 = 0.03359 -0.00733 -0.00099 -0.00374 AFIX 43 H31 2 0.184513 0.881440 0.720051 11.00000 -1.20000 AFIX 0 C32 1 0.357283 0.836387 0.796400 11.00000 0.03146 0.02250 = 0.04240 -0.01155 0.00266 -0.00669 AFIX 43 H32 2 0.454654 0.874197 0.771658 11.00000 -1.20000 AFIX 0 C33 1 0.604453 0.502529 0.488703 11.00000 0.02043 0.02921 = 0.02750 -0.00555 -0.00478 -0.00476 C34 1 0.597877 0.984859 0.486819 11.00000 0.02503 0.02853 = 0.03720 -0.00307 -0.00047 0.00171 CL1 3 0.369822 0.002063 0.914330 11.00000 0.05042 0.03406 = 0.04661 -0.01251 -0.01447 0.00330 CL2A 3 -0.247523 -0.178699 0.985959 21.00000 0.06710 0.02980 = 0.05774 -0.01622 0.03220 -0.02189 CL2B 3 -0.206728 -0.186012 1.007899 -21.00000 0.05447 0.02764 = 0.04483 -0.01104 0.01755 -0.01432 CL3 3 -0.406485 0.222125 0.850952 11.00000 0.05102 0.05006 = 0.06419 -0.01935 0.01936 -0.02064 CL4 3 0.099063 0.451250 0.837194 11.00000 0.02464 0.02517 = 0.03810 -0.00585 -0.01078 0.00031 CL5 3 -0.592516 0.390972 0.961741 11.00000 0.02967 0.03393 = 0.03547 0.00025 -0.00675 -0.01064 CL6 3 0.042321 0.637074 0.949352 11.00000 0.03766 0.03167 = 0.02525 -0.00018 -0.00588 -0.00762 S1 4 -0.393186 0.387256 0.722121 11.00000 0.04059 0.04794 = 0.05509 -0.03089 -0.01525 0.01200 S2 4 0.352478 0.754808 0.883425 11.00000 0.02754 0.02791 = 0.04198 -0.01374 -0.00932 -0.00049 N1 5 0.445565 0.155579 0.655274 11.00000 0.02711 0.02175 = 0.03737 -0.00666 0.00008 -0.00219 N2 5 0.562381 0.277384 0.583337 11.00000 0.03556 0.02375 = 0.03431 -0.00678 0.00091 -0.00464 N3 5 0.233669 0.667511 0.641360 11.00000 0.02525 0.02766 = 0.02410 -0.00630 -0.00339 -0.00119 N4 5 0.412619 0.775566 0.591160 11.00000 0.02992 0.02987 = 0.02911 0.00141 -0.00367 -0.00620 O1 6 0.094514 0.187549 0.740334 11.00000 0.03363 0.02028 = 0.03805 -0.00950 -0.00206 0.00274 O2 6 -0.082157 0.722764 0.733207 11.00000 0.02959 0.02074 = 0.02493 -0.00518 -0.00760 -0.00043 O3 6 0.691178 0.431757 0.498938 11.00000 0.02160 0.02821 = 0.03877 -0.00631 -0.00393 -0.00179 O4 6 0.668718 0.576486 0.462218 11.00000 0.02262 0.02678 = 0.06695 -0.00101 -0.00943 -0.00639 O5 6 0.632911 0.905576 0.516137 11.00000 0.02501 0.02884 = 0.05755 0.00055 0.00215 0.00179 O6 6 0.701768 1.040311 0.440834 11.00000 0.02742 0.03087 = 0.05497 0.00263 0.00637 0.00047 O7 6 0.949626 0.632405 0.506761 11.00000 0.02692 0.04321 = 0.04105 -0.01879 -0.01103 0.00413 O8 6 0.940842 0.807623 0.508016 11.00000 0.02707 0.03715 = 0.05465 -0.00799 -0.00772 0.00495 O9 6 1.017932 0.967067 0.384861 11.00000 0.02981 0.03639 = 0.05027 -0.00444 0.00463 -0.00004 O10 6 1.319459 1.062052 0.325329 11.00000 0.03923 0.03592 = 0.04605 -0.00523 0.00193 -0.00999 H2N 2 0.577889 0.330492 0.551765 11.00000 0.05801 H4N 2 0.461034 0.829567 0.568481 11.00000 0.04812 H7A 2 0.880122 0.608058 0.493321 11.00000 0.04068 H7N 2 1.043846 0.604942 0.503194 11.00000 0.03752 H8C 2 0.843723 0.831341 0.513496 11.00000 0.04109 H8D 2 0.928566 0.755464 0.503449 11.00000 0.04394 H9A 2 0.923728 0.992895 0.404090 11.00000 0.05428 H9B 2 1.025914 0.922181 0.424748 11.00000 0.06423 H10A 2 1.222459 1.035038 0.349212 11.00000 0.04971 H10B 2 1.342086 1.083341 0.363137 11.00000 0.10228 HKLF 4 REM AM230915b in P-1 REM wR2 = 0.1414, GooF = S = 1.095, Restrained GooF = 1.095 for all data REM R1 = 0.0492 for 7474 Fo > 4sig(Fo) and 0.0555 for all 8721 data REM 555 parameters refined using 0 restraints END WGHT 0.0822 0.4317 REM Highest difference peak 0.543, deepest hole -0.498, 1-sigma level 0.080 Q1 1 0.0220 0.6170 1.0147 11.00000 0.05 0.54 Q2 1 0.1218 0.4708 0.7764 11.00000 0.05 0.52 ; _shelx_res_checksum 69457 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 0.0992(3) 0.04282(14) 0.83131(16) 0.0322(5) Uani 1 1 d . . . . . C2 C 0.1608(3) -0.01222(15) 0.89645(15) 0.0329(5) Uani 1 1 d . . . . . C3 C 0.0621(4) -0.08133(16) 0.94841(17) 0.0435(6) Uani 1 1 d . . . . . H3 H 0.106286 -0.117867 0.992808 0.052 Uiso 1 1 calc R U . . . C4 C -0.1021(4) -0.09559(17) 0.9338(2) 0.0516(8) Uani 1 1 d . . . . . C5 C -0.1669(4) -0.04305(19) 0.8692(2) 0.0553(9) Uani 1 1 d . . . . . H5 H -0.279344 -0.054136 0.859501 0.066 Uiso 1 1 calc R U . . . C6 C -0.0662(3) 0.02587(17) 0.8186(2) 0.0446(7) Uani 1 1 d . . . . . H6 H -0.111048 0.062268 0.774303 0.054 Uiso 1 1 calc R U . . . C7 C 0.2069(3) 0.11767(14) 0.77348(15) 0.0303(5) Uani 1 1 d . . . . . H7 H 0.288999 0.138858 0.800992 0.036 Uiso 1 1 calc R U . . . C8 C 0.3149(3) 0.08935(14) 0.70197(16) 0.0318(5) Uani 1 1 d . . . . . H8A H 0.377466 0.033241 0.720839 0.038 Uiso 1 1 calc R U . . . H8B H 0.233555 0.080942 0.668120 0.038 Uiso 1 1 calc R U . . . C9 C 0.4116(3) 0.23410(15) 0.60988(15) 0.0318(5) Uani 1 1 d . . . . . H9 H 0.298058 0.255533 0.598424 0.038 Uiso 1 1 calc R U . . . C10 C 0.6971(3) 0.22626(17) 0.61295(17) 0.0368(5) Uani 1 1 d . . . . . H10 H 0.818582 0.241625 0.603708 0.044 Uiso 1 1 calc R U . . . C11 C 0.6250(3) 0.14975(16) 0.65783(16) 0.0347(5) Uani 1 1 d . . . . . H11 H 0.686427 0.100993 0.685918 0.042 Uiso 1 1 calc R U . . . C12 C 0.0234(3) 0.23942(15) 0.79395(16) 0.0344(5) Uani 1 1 d . . . . . H12A H 0.120948 0.269230 0.804447 0.041 Uiso 1 1 calc R U . . . H12B H -0.038775 0.202096 0.845203 0.041 Uiso 1 1 calc R U . . . C13 C -0.2852(3) 0.30096(16) 0.77754(17) 0.0360(5) Uani 1 1 d . . . . . C14 C -0.1039(3) 0.30459(15) 0.75604(15) 0.0313(5) Uani 1 1 d . . . . . C15 C -0.0528(3) 0.37962(15) 0.69130(15) 0.0337(5) Uani 1 1 d . . . . . H15 H 0.067917 0.393217 0.667263 0.040 Uiso 1 1 calc R U . . . C16 C -0.1935(4) 0.42965(18) 0.66745(17) 0.0413(6) Uani 1 1 d . . . . . H16 H -0.182320 0.481895 0.625460 0.050 Uiso 1 1 calc R U . . . C17 C -0.1630(3) 0.57232(13) 0.80089(12) 0.0227(4) Uani 1 1 d . . . . . C18 C -0.1222(3) 0.48782(14) 0.84232(13) 0.0239(4) Uani 1 1 d . . . . . C19 C -0.2522(3) 0.43066(14) 0.89091(13) 0.0263(4) Uani 1 1 d . . . . . H19 H -0.221486 0.373138 0.918154 0.032 Uiso 1 1 calc R U . . . C20 C -0.4289(3) 0.46022(14) 0.89850(13) 0.0262(4) Uani 1 1 d . . . . . C21 C -0.4759(3) 0.54307(14) 0.85771(13) 0.0261(4) Uani 1 1 d . . . . . H21 H -0.597376 0.561967 0.862799 0.031 Uiso 1 1 calc R U . . . C22 C -0.3420(3) 0.59805(14) 0.80921(13) 0.0253(4) Uani 1 1 d . . . . . H22 H -0.373535 0.654945 0.780833 0.030 Uiso 1 1 calc R U . . . C23 C -0.0173(3) 0.63563(13) 0.75283(12) 0.0228(4) Uani 1 1 d . . . . . H23 H 0.077295 0.631655 0.785081 0.027 Uiso 1 1 calc R U . . . C24 C 0.0691(3) 0.61810(15) 0.67336(13) 0.0269(4) Uani 1 1 d . . . . . H24A H 0.096537 0.555139 0.681128 0.032 Uiso 1 1 calc R U . . . H24B H -0.013911 0.635953 0.635479 0.032 Uiso 1 1 calc R U . . . C25 C 0.2451(3) 0.75194(14) 0.60273(13) 0.0273(4) Uani 1 1 d . . . . . H25 H 0.148988 0.788925 0.586274 0.033 Uiso 1 1 calc R U . . . C26 C 0.5121(3) 0.70455(18) 0.62381(17) 0.0389(6) Uani 1 1 d . . . . . H26 H 0.636243 0.703334 0.624033 0.047 Uiso 1 1 calc R U . . . C27 C 0.4011(3) 0.63701(17) 0.65542(16) 0.0355(5) Uani 1 1 d . . . . . H27 H 0.431954 0.579369 0.682274 0.043 Uiso 1 1 calc R U . . . C28 C -0.0993(3) 0.76451(14) 0.79655(13) 0.0268(4) Uani 1 1 d . . . . . H28A H -0.175420 0.728953 0.844963 0.032 Uiso 1 1 calc R U . . . H28B H -0.158826 0.822153 0.780958 0.032 Uiso 1 1 calc R U . . . C29 C 0.1443(3) 0.72508(14) 0.87845(13) 0.0253(4) Uani 1 1 d . . . . . C30 C 0.0789(3) 0.77602(13) 0.81501(13) 0.0246(4) Uani 1 1 d . . . . . C31 C 0.2051(3) 0.84011(14) 0.76745(15) 0.0306(5) Uani 1 1 d . . . . . H31 H 0.184513 0.881440 0.720051 0.037 Uiso 1 1 calc R U . . . C32 C 0.3573(3) 0.83639(15) 0.79640(16) 0.0326(5) Uani 1 1 d . . . . . H32 H 0.454654 0.874197 0.771658 0.039 Uiso 1 1 calc R U . . . C33 C 0.6045(2) 0.50253(14) 0.48870(13) 0.0259(4) Uani 1 1 d . . . . . C34 C 0.5979(3) 0.98486(16) 0.48682(15) 0.0324(5) Uani 1 1 d . . . . . Cl1 Cl 0.36982(9) 0.00206(4) 0.91433(4) 0.04281(16) Uani 1 1 d . . . . . Cl2A Cl -0.248(2) -0.1787(5) 0.9860(11) 0.056(2) Uani 0.53(4) 1 d . . P . . Cl2B Cl -0.2067(13) -0.1860(3) 1.0079(8) 0.0453(13) Uani 0.47(4) 1 d . . P . . Cl3 Cl -0.40649(10) 0.22212(5) 0.85095(5) 0.0577(2) Uani 1 1 d . . . . . Cl4 Cl 0.09906(6) 0.45125(3) 0.83719(3) 0.02919(13) Uani 1 1 d . . . . . Cl5 Cl -0.59252(7) 0.39097(4) 0.96174(3) 0.03436(14) Uani 1 1 d . . . . . Cl6 Cl 0.04232(7) 0.63707(4) 0.94935(3) 0.03270(14) Uani 1 1 d . . . . . S1 S -0.39319(9) 0.38726(5) 0.72212(5) 0.04418(17) Uani 1 1 d . . . . . S2 S 0.35248(7) 0.75481(4) 0.88342(4) 0.03119(14) Uani 1 1 d . . . . . N1 N 0.4456(2) 0.15558(12) 0.65527(12) 0.0298(4) Uani 1 1 d . . . . . N2 N 0.5624(3) 0.27738(13) 0.58334(13) 0.0323(4) Uani 1 1 d . . . . . N3 N 0.2337(2) 0.66751(12) 0.64136(11) 0.0260(4) Uani 1 1 d . . . . . N4 N 0.4126(3) 0.77557(14) 0.59116(12) 0.0315(4) Uani 1 1 d . . . . . O1 O 0.0945(2) 0.18755(10) 0.74033(10) 0.0312(3) Uani 1 1 d . . . . . O2 O -0.08216(19) 0.72276(9) 0.73321(9) 0.0249(3) Uani 1 1 d . . . . . O3 O 0.69118(19) 0.43176(10) 0.49894(10) 0.0303(3) Uani 1 1 d . . . . . O4 O 0.6687(2) 0.57649(11) 0.46222(13) 0.0407(4) Uani 1 1 d . . . . . O5 O 0.6329(2) 0.90558(12) 0.51614(13) 0.0412(4) Uani 1 1 d . . . . . O6 O 0.7018(2) 1.04031(12) 0.44083(13) 0.0428(4) Uani 1 1 d . . . . . O7 O 0.9496(2) 0.63240(13) 0.50676(11) 0.0351(4) Uani 1 1 d . . . . . O8 O 0.9408(2) 0.80762(13) 0.50802(13) 0.0408(4) Uani 1 1 d . . . . . O9 O 1.0179(2) 0.96707(14) 0.38486(13) 0.0421(4) Uani 1 1 d . . . . . O10 O 1.3195(3) 1.06205(13) 0.32533(13) 0.0426(4) Uani 1 1 d . . . . . H2N H 0.578(5) 0.330(3) 0.552(2) 0.058(10) Uiso 1 1 d . . . . . H4N H 0.461(5) 0.830(2) 0.568(2) 0.048(9) Uiso 1 1 d . . . . . H7A H 0.880(5) 0.608(2) 0.493(2) 0.041(8) Uiso 1 1 d . . . . . H7N H 1.044(5) 0.605(2) 0.5032(19) 0.038(8) Uiso 1 1 d . . . . . H8C H 0.844(5) 0.831(2) 0.513(2) 0.041(8) Uiso 1 1 d . . . . . H8D H 0.929(4) 0.755(3) 0.503(2) 0.044(9) Uiso 1 1 d . . . . . H9A H 0.924(5) 0.993(3) 0.404(2) 0.054(10) Uiso 1 1 d . . . . . H9B H 1.026(5) 0.922(3) 0.425(3) 0.064(12) Uiso 1 1 d . . . . . H10A H 1.222(5) 1.035(3) 0.349(2) 0.050(9) Uiso 1 1 d . . . . . H10B H 1.342(7) 1.083(4) 0.363(4) 0.102(18) 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 0.0300(10) 0.0192(10) 0.0439(13) -0.0090(9) 0.0015(9) -0.0002(8) C2 0.0373(11) 0.0231(10) 0.0358(12) -0.0114(9) 0.0039(10) -0.0007(9) C3 0.0616(16) 0.0228(11) 0.0371(13) -0.0106(10) 0.0158(12) -0.0037(11) C4 0.0539(16) 0.0222(12) 0.065(2) -0.0182(12) 0.0332(14) -0.0119(11) C5 0.0322(12) 0.0291(13) 0.099(3) -0.0243(16) 0.0122(14) -0.0105(10) C6 0.0313(12) 0.0268(12) 0.073(2) -0.0115(12) -0.0058(12) -0.0017(9) C7 0.0297(10) 0.0177(9) 0.0411(13) -0.0062(9) -0.0032(9) -0.0015(8) C8 0.0286(10) 0.0190(10) 0.0444(13) -0.0078(9) 0.0007(9) -0.0022(8) C9 0.0308(11) 0.0238(10) 0.0378(12) -0.0052(9) -0.0035(9) -0.0010(8) C10 0.0275(10) 0.0342(12) 0.0462(14) -0.0120(11) 0.0008(10) -0.0011(9) C11 0.0246(10) 0.0295(11) 0.0463(14) -0.0087(10) -0.0008(9) 0.0015(8) C12 0.0417(12) 0.0234(10) 0.0391(13) -0.0125(9) -0.0054(10) 0.0029(9) C13 0.0336(11) 0.0307(12) 0.0453(14) -0.0185(11) 0.0015(10) -0.0033(9) C14 0.0364(11) 0.0234(10) 0.0354(12) -0.0139(9) -0.0014(9) -0.0011(8) C15 0.0431(12) 0.0258(11) 0.0344(12) -0.0138(9) -0.0036(10) -0.0037(9) C16 0.0599(16) 0.0317(12) 0.0375(13) -0.0144(10) -0.0162(12) 0.0053(11) C17 0.0262(9) 0.0223(9) 0.0213(9) -0.0075(8) -0.0064(7) -0.0006(7) C18 0.0261(9) 0.0231(9) 0.0255(10) -0.0076(8) -0.0095(8) -0.0014(7) C19 0.0308(10) 0.0221(10) 0.0278(10) -0.0048(8) -0.0107(8) -0.0050(8) C20 0.0276(10) 0.0258(10) 0.0251(10) -0.0061(8) -0.0040(8) -0.0064(8) C21 0.0235(9) 0.0270(10) 0.0302(11) -0.0105(9) -0.0060(8) -0.0013(7) C22 0.0277(10) 0.0216(9) 0.0286(10) -0.0076(8) -0.0089(8) 0.0009(7) C23 0.0262(9) 0.0191(9) 0.0239(10) -0.0058(7) -0.0062(8) -0.0013(7) C24 0.0277(10) 0.0281(10) 0.0256(10) -0.0087(8) -0.0026(8) -0.0067(8) C25 0.0283(10) 0.0262(10) 0.0244(10) -0.0026(8) -0.0035(8) -0.0013(8) C26 0.0244(10) 0.0416(14) 0.0416(14) 0.0024(11) -0.0042(10) -0.0010(9) C27 0.0273(10) 0.0327(12) 0.0402(13) -0.0012(10) -0.0062(10) 0.0044(9) C28 0.0290(10) 0.0235(10) 0.0285(11) -0.0089(8) -0.0045(8) 0.0000(8) C29 0.0273(9) 0.0232(9) 0.0267(10) -0.0098(8) -0.0029(8) -0.0021(7) C30 0.0269(9) 0.0195(9) 0.0281(10) -0.0092(8) -0.0024(8) -0.0012(7) C31 0.0361(11) 0.0203(10) 0.0336(12) -0.0073(9) -0.0010(9) -0.0037(8) C32 0.0315(11) 0.0225(10) 0.0424(13) -0.0115(9) 0.0027(9) -0.0067(8) C33 0.0204(10) 0.0292(11) 0.0275(10) -0.0056(8) -0.0048(8) -0.0048(8) C34 0.0250(10) 0.0285(11) 0.0372(12) -0.0031(9) -0.0005(9) 0.0017(8) Cl1 0.0504(3) 0.0341(3) 0.0466(4) -0.0125(3) -0.0145(3) 0.0033(2) Cl2A 0.067(3) 0.0298(11) 0.058(4) -0.0162(17) 0.032(3) -0.0219(15) Cl2B 0.0545(19) 0.0276(9) 0.045(2) -0.0110(11) 0.0176(17) -0.0143(10) Cl3 0.0510(4) 0.0501(4) 0.0642(5) -0.0194(4) 0.0194(3) -0.0206(3) Cl4 0.0246(2) 0.0252(2) 0.0381(3) -0.0058(2) -0.0108(2) 0.00031(17) Cl5 0.0297(3) 0.0339(3) 0.0355(3) 0.0003(2) -0.0068(2) -0.0106(2) Cl6 0.0377(3) 0.0317(3) 0.0252(3) -0.0002(2) -0.0059(2) -0.0076(2) S1 0.0406(3) 0.0479(4) 0.0551(4) -0.0309(3) -0.0152(3) 0.0120(3) S2 0.0275(2) 0.0279(3) 0.0420(3) -0.0137(2) -0.0093(2) -0.00049(19) N1 0.0271(9) 0.0217(9) 0.0374(10) -0.0067(8) 0.0001(8) -0.0022(7) N2 0.0356(10) 0.0238(9) 0.0343(10) -0.0068(8) 0.0009(8) -0.0046(7) N3 0.0253(8) 0.0277(9) 0.0241(9) -0.0063(7) -0.0034(7) -0.0012(7) N4 0.0299(9) 0.0299(10) 0.0291(10) 0.0014(8) -0.0037(7) -0.0062(7) O1 0.0336(8) 0.0203(7) 0.0381(9) -0.0095(6) -0.0021(7) 0.0027(6) O2 0.0296(7) 0.0207(7) 0.0249(7) -0.0052(6) -0.0076(6) -0.0004(5) O3 0.0216(7) 0.0282(8) 0.0388(9) -0.0063(7) -0.0039(6) -0.0018(6) O4 0.0226(7) 0.0268(8) 0.0670(13) -0.0010(8) -0.0094(8) -0.0064(6) O5 0.0250(7) 0.0288(8) 0.0576(12) 0.0005(8) 0.0021(7) 0.0018(6) O6 0.0274(8) 0.0309(9) 0.0550(12) 0.0026(8) 0.0064(8) 0.0005(6) O7 0.0269(8) 0.0432(10) 0.0410(10) -0.0188(8) -0.0110(7) 0.0041(7) O8 0.0271(8) 0.0371(10) 0.0546(12) -0.0080(9) -0.0077(8) 0.0049(7) O9 0.0298(8) 0.0364(10) 0.0503(12) -0.0044(9) 0.0046(8) 0.0000(7) O10 0.0392(10) 0.0359(10) 0.0460(11) -0.0052(8) 0.0019(8) -0.0100(8) 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' Cl Cl 0.3639 0.7018 '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' 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' 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 117.7(2) . . ? C6 C1 C7 119.5(2) . . ? C2 C1 C7 122.7(2) . . ? C3 C2 C1 122.2(3) . . ? C3 C2 Cl1 117.2(2) . . ? C1 C2 Cl1 120.54(18) . . ? C4 C3 C2 118.2(3) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C3 C4 C5 121.3(2) . . ? C3 C4 Cl2A 127.9(9) . . ? C5 C4 Cl2A 110.7(9) . . ? C3 C4 Cl2B 110.8(6) . . ? C5 C4 Cl2B 127.9(6) . . ? Cl2A C4 Cl2B 17.4(4) . . ? C4 C5 C6 119.3(3) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C1 121.2(3) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? O1 C7 C1 111.58(18) . . ? O1 C7 C8 104.99(19) . . ? C1 C7 C8 110.63(18) . . ? O1 C7 H7 109.8 . . ? C1 C7 H7 109.8 . . ? C8 C7 H7 109.8 . . ? N1 C8 C7 110.05(18) . . ? N1 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? N1 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.2 . . ? N2 C9 N1 108.7(2) . . ? N2 C9 H9 125.7 . . ? N1 C9 H9 125.7 . . ? C11 C10 N2 107.0(2) . . ? C11 C10 H10 126.5 . . ? N2 C10 H10 126.5 . . ? C10 C11 N1 107.2(2) . . ? C10 C11 H11 126.4 . . ? N1 C11 H11 126.4 . . ? O1 C12 C14 107.8(2) . . ? O1 C12 H12A 110.1 . . ? C14 C12 H12A 110.1 . . ? O1 C12 H12B 110.1 . . ? C14 C12 H12B 110.1 . . ? H12A C12 H12B 108.5 . . ? C14 C13 Cl3 127.0(2) . . ? C14 C13 S1 113.2(2) . . ? Cl3 C13 S1 119.86(15) . . ? C13 C14 C15 110.4(2) . . ? C13 C14 C12 125.0(2) . . ? C15 C14 C12 124.6(2) . . ? C16 C15 C14 113.5(2) . . ? C16 C15 H15 123.2 . . ? C14 C15 H15 123.2 . . ? C15 C16 S1 111.9(2) . . ? C15 C16 H16 124.0 . . ? S1 C16 H16 124.0 . . ? C22 C17 C18 117.38(19) . . ? C22 C17 C23 121.17(19) . . ? C18 C17 C23 121.34(18) . . ? C19 C18 C17 122.44(19) . . ? C19 C18 Cl4 117.19(16) . . ? C17 C18 Cl4 120.34(16) . . ? C18 C19 C20 117.9(2) . . ? C18 C19 H19 121.0 . . ? C20 C19 H19 121.0 . . ? C21 C20 C19 121.7(2) . . ? C21 C20 Cl5 119.78(17) . . ? C19 C20 Cl5 118.56(17) . . ? C20 C21 C22 118.66(19) . . ? C20 C21 H21 120.7 . . ? C22 C21 H21 120.7 . . ? C21 C22 C17 121.9(2) . . ? C21 C22 H22 119.0 . . ? C17 C22 H22 119.0 . . ? O2 C23 C17 112.26(16) . . ? O2 C23 C24 105.28(17) . . ? C17 C23 C24 113.53(16) . . ? O2 C23 H23 108.5 . . ? C17 C23 H23 108.5 . . ? C24 C23 H23 108.5 . . ? N3 C24 C23 108.95(17) . . ? N3 C24 H24A 109.9 . . ? C23 C24 H24A 109.9 . . ? N3 C24 H24B 109.9 . . ? C23 C24 H24B 109.9 . . ? H24A C24 H24B 108.3 . . ? N4 C25 N3 108.69(19) . . ? N4 C25 H25 125.7 . . ? N3 C25 H25 125.7 . . ? C27 C26 N4 107.4(2) . . ? C27 C26 H26 126.3 . . ? N4 C26 H26 126.3 . . ? C26 C27 N3 106.9(2) . . ? C26 C27 H27 126.5 . . ? N3 C27 H27 126.5 . . ? O2 C28 C30 111.77(16) . . ? O2 C28 H28A 109.3 . . ? C30 C28 H28A 109.3 . . ? O2 C28 H28B 109.3 . . ? C30 C28 H28B 109.3 . . ? H28A C28 H28B 107.9 . . ? C30 C29 Cl6 126.75(17) . . ? C30 C29 S2 113.48(17) . . ? Cl6 C29 S2 119.77(13) . . ? C29 C30 C31 110.56(19) . . ? C29 C30 C28 124.5(2) . . ? C31 C30 C28 124.9(2) . . ? C32 C31 C30 113.6(2) . . ? C32 C31 H31 123.2 . . ? C30 C31 H31 123.2 . . ? C31 C32 S2 111.81(17) . . ? C31 C32 H32 124.1 . . ? S2 C32 H32 124.1 . . ? O4 C33 O3 126.02(18) . . ? O4 C33 C33 116.9(2) . 2_666 ? O3 C33 C33 117.1(2) . 2_666 ? O6 C34 O5 127.1(2) . . ? O6 C34 C34 117.4(3) . 2_676 ? O5 C34 C34 115.5(3) . 2_676 ? Cl2B Cl2A C4 86.6(13) . . ? Cl2A Cl2B C4 76.1(10) . . ? C16 S1 C13 90.94(13) . . ? C32 S2 C29 90.54(11) . . ? C9 N1 C11 108.07(19) . . ? C9 N1 C8 126.85(19) . . ? C11 N1 C8 124.8(2) . . ? C9 N2 C10 109.1(2) . . ? C9 N2 H2N 127(2) . . ? C10 N2 H2N 123(2) . . ? C25 N3 C27 108.26(19) . . ? C25 N3 C24 126.15(18) . . ? C27 N3 C24 125.1(2) . . ? C25 N4 C26 108.7(2) . . ? C25 N4 H4N 129(2) . . ? C26 N4 H4N 122(2) . . ? C7 O1 C12 112.76(19) . . ? C23 O2 C28 114.00(16) . . ? H7A O7 H7N 107(3) . . ? H8C O8 H8D 109(3) . . ? H9A O9 H9B 101(4) . . ? H10A O10 H10B 101(4) . . ? 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 1.389(4) . ? C1 C2 1.391(4) . ? C1 C7 1.515(3) . ? C2 C3 1.387(4) . ? C2 Cl1 1.736(3) . ? C3 C4 1.381(5) . ? C3 H3 0.9500 . ? C4 C5 1.382(5) . ? C4 Cl2A 1.729(5) . ? C4 Cl2B 1.778(6) . ? C5 C6 1.384(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.425(3) . ? C7 C8 1.532(3) . ? C7 H7 1.0000 . ? C8 N1 1.465(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N2 1.324(3) . ? C9 N1 1.330(3) . ? C9 H9 0.9500 . ? C10 C11 1.349(4) . ? C10 N2 1.365(3) . ? C10 H10 0.9500 . ? C11 N1 1.379(3) . ? C11 H11 0.9500 . ? C12 O1 1.435(3) . ? C12 C14 1.488(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.363(3) . ? C13 Cl3 1.712(3) . ? C13 S1 1.722(3) . ? C14 C15 1.429(4) . ? C15 C16 1.359(4) . ? C15 H15 0.9500 . ? C16 S1 1.712(3) . ? C16 H16 0.9500 . ? C17 C22 1.391(3) . ? C17 C18 1.394(3) . ? C17 C23 1.518(3) . ? C18 C19 1.387(3) . ? C18 Cl4 1.742(2) . ? C19 C20 1.392(3) . ? C19 H19 0.9500 . ? C20 C21 1.383(3) . ? C20 Cl5 1.734(2) . ? C21 C22 1.388(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 O2 1.416(2) . ? C23 C24 1.527(3) . ? C23 H23 1.0000 . ? C24 N3 1.465(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N4 1.324(3) . ? C25 N3 1.335(3) . ? C25 H25 0.9500 . ? C26 C27 1.347(4) . ? C26 N4 1.375(3) . ? C26 H26 0.9500 . ? C27 N3 1.382(3) . ? C27 H27 0.9500 . ? C28 O2 1.443(2) . ? C28 C30 1.502(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.359(3) . ? C29 Cl6 1.722(2) . ? C29 S2 1.723(2) . ? C30 C31 1.427(3) . ? C31 C32 1.357(4) . ? C31 H31 0.9500 . ? C32 S2 1.722(3) . ? C32 H32 0.9500 . ? C33 O4 1.244(3) . ? C33 O3 1.255(3) . ? C33 C33 1.570(4) 2_666 ? C34 O6 1.237(3) . ? C34 O5 1.261(3) . ? C34 C34 1.559(4) 2_676 ? Cl2A Cl2B 0.531(11) . ? N2 H2N 0.88(4) . ? N4 H4N 0.92(4) . ? O7 H7A 0.79(4) . ? O7 H7N 0.82(4) . ? O8 H8C 0.81(4) . ? O8 H8D 0.87(4) . ? O9 H9A 0.86(4) . ? O9 H9B 0.87(5) . ? O10 H10A 0.86(4) . ? O10 H10B 0.89(6) . ? 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 -179.1(2) . . . . ? C6 C1 C2 Cl1 177.55(19) . . . . ? C7 C1 C2 Cl1 -0.6(3) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? Cl1 C2 C3 C4 -177.97(18) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C2 C3 C4 Cl2A 177.1(3) . . . . ? C2 C3 C4 Cl2B -179.3(3) . . . . ? C3 C4 C5 C6 -0.8(4) . . . . ? Cl2A C4 C5 C6 -178.1(3) . . . . ? Cl2B C4 C5 C6 178.7(3) . . . . ? C4 C5 C6 C1 0.5(4) . . . . ? C2 C1 C6 C5 0.4(4) . . . . ? C7 C1 C6 C5 178.6(2) . . . . ? C6 C1 C7 O1 32.3(3) . . . . ? C2 C1 C7 O1 -149.6(2) . . . . ? C6 C1 C7 C8 -84.2(3) . . . . ? C2 C1 C7 C8 93.9(3) . . . . ? O1 C7 C8 N1 71.2(2) . . . . ? C1 C7 C8 N1 -168.26(19) . . . . ? N2 C10 C11 N1 -0.3(3) . . . . ? Cl3 C13 C14 C15 179.02(18) . . . . ? S1 C13 C14 C15 -1.0(3) . . . . ? Cl3 C13 C14 C12 -0.5(4) . . . . ? S1 C13 C14 C12 179.44(18) . . . . ? O1 C12 C14 C13 105.5(3) . . . . ? O1 C12 C14 C15 -74.0(3) . . . . ? C13 C14 C15 C16 0.9(3) . . . . ? C12 C14 C15 C16 -179.5(2) . . . . ? C14 C15 C16 S1 -0.4(3) . . . . ? C22 C17 C18 C19 -0.6(3) . . . . ? C23 C17 C18 C19 175.58(19) . . . . ? C22 C17 C18 Cl4 -178.40(15) . . . . ? C23 C17 C18 Cl4 -2.2(3) . . . . ? C17 C18 C19 C20 -0.7(3) . . . . ? Cl4 C18 C19 C20 177.15(16) . . . . ? C18 C19 C20 C21 1.6(3) . . . . ? C18 C19 C20 Cl5 -177.75(16) . . . . ? C19 C20 C21 C22 -1.1(3) . . . . ? Cl5 C20 C21 C22 178.22(16) . . . . ? C20 C21 C22 C17 -0.3(3) . . . . ? C18 C17 C22 C21 1.1(3) . . . . ? C23 C17 C22 C21 -175.08(19) . . . . ? C22 C17 C23 O2 11.7(3) . . . . ? C18 C17 C23 O2 -164.37(17) . . . . ? C22 C17 C23 C24 -107.6(2) . . . . ? C18 C17 C23 C24 76.4(2) . . . . ? O2 C23 C24 N3 70.6(2) . . . . ? C17 C23 C24 N3 -166.17(17) . . . . ? N4 C26 C27 N3 0.3(3) . . . . ? Cl6 C29 C30 C31 -177.29(16) . . . . ? S2 C29 C30 C31 1.7(2) . . . . ? Cl6 C29 C30 C28 1.1(3) . . . . ? S2 C29 C30 C28 -179.94(15) . . . . ? O2 C28 C30 C29 -102.5(2) . . . . ? O2 C28 C30 C31 75.7(2) . . . . ? C29 C30 C31 C32 -0.8(3) . . . . ? C28 C30 C31 C32 -179.20(19) . . . . ? C30 C31 C32 S2 -0.4(2) . . . . ? C3 C4 Cl2A Cl2B 11.4(11) . . . . ? C5 C4 Cl2A Cl2B -171.6(10) . . . . ? C3 C4 Cl2B Cl2A -170.4(9) . . . . ? C5 C4 Cl2B Cl2A 10.0(11) . . . . ? C15 C16 S1 C13 -0.1(2) . . . . ? C14 C13 S1 C16 0.7(2) . . . . ? Cl3 C13 S1 C16 -179.35(16) . . . . ? C31 C32 S2 C29 1.11(18) . . . . ? C30 C29 S2 C32 -1.62(17) . . . . ? Cl6 C29 S2 C32 177.42(14) . . . . ? N2 C9 N1 C11 0.5(3) . . . . ? N2 C9 N1 C8 174.4(2) . . . . ? C10 C11 N1 C9 -0.1(3) . . . . ? C10 C11 N1 C8 -174.1(2) . . . . ? C7 C8 N1 C9 -71.1(3) . . . . ? C7 C8 N1 C11 101.8(2) . . . . ? N1 C9 N2 C10 -0.8(3) . . . . ? C11 C10 N2 C9 0.7(3) . . . . ? N4 C25 N3 C27 0.7(3) . . . . ? N4 C25 N3 C24 172.8(2) . . . . ? C26 C27 N3 C25 -0.6(3) . . . . ? C26 C27 N3 C24 -172.9(2) . . . . ? C23 C24 N3 C25 -80.1(3) . . . . ? C23 C24 N3 C27 90.8(3) . . . . ? N3 C25 N4 C26 -0.5(3) . . . . ? C27 C26 N4 C25 0.1(3) . . . . ? C1 C7 O1 C12 77.9(2) . . . . ? C8 C7 O1 C12 -162.25(18) . . . . ? C14 C12 O1 C7 -174.84(18) . . . . ? C17 C23 O2 C28 81.0(2) . . . . ? C24 C23 O2 C28 -155.03(16) . . . . ? C30 C28 O2 C23 65.8(2) . . . . ?