#------------------------------------------------------------------------------ #$Date: 2025-03-09 01:57:00 +0200 (Sun, 09 Mar 2025) $ #$Revision: 298347 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/40/1574096.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_1574096 loop_ _publ_author_name 'Duan, Tainan' 'Wang, Jia' 'Zuo, Xiaochan' 'Zhong, Yanyi' 'Long, Yuhong' 'Wang, Peiran' 'Tu, Kaihuai' 'Zhong, Cheng' 'Zhang, Jiangbin' 'Rakitin, Oleg Alekseevich' 'Yao, Zhaoyang' 'Wan, Xiangjian' 'Zhao, Yan' 'Kan, Bin' 'Chen, Yongsheng' _publ_section_title ; “Head Surgery” of Polycyclic o-Quinones with Cyanated Aromatic Rings towards High Electron Mobility Acceptors Enable 19.6% Additive-Free Binary Organic Solar Cells ; _journal_name_full 'Energy & Environmental Science' _journal_paper_doi 10.1039/D5EE00031A _journal_year 2025 _chemical_formula_moiety 'C90 H94 Cl4 N8 O2 S5' _chemical_formula_sum 'C90 H94 Cl4 N8 O2 S5' _chemical_formula_weight 1621.83 _chemical_name_systematic CD-2 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2025-02-19 _audit_creation_method ; Olex2 1.5 (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _audit_update_record ; 2025-02-21 deposited with the CCDC. 2025-03-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 111.957(11) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 29.131(5) _cell_length_b 22.225(4) _cell_length_c 14.008(2) _cell_measurement_reflns_used 3395 _cell_measurement_temperature 223.00 _cell_measurement_theta_max 62.83 _cell_measurement_theta_min 2.57 _cell_volume 8411(2) _computing_cell_refinement 'SAINT V8.40B (Bruker, 2019)' _computing_data_collection 'APEX6 V2024.9-0 (Bruker, 2024)' _computing_data_reduction 'SAINT V8.40B (Bruker, 2019)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 223.00 _diffrn_detector CPAD _diffrn_detector_area_resol_mean 7.41 _diffrn_detector_type 'Bruker PHOTON III' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Bruker D8 VENTURE dual wavelength Mo/Cu' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator 'Helios Multi-layer Optic' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0954 _diffrn_reflns_av_unetI/netI 0.0883 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 24569 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 50.434 _diffrn_reflns_theta_max 50.434 _diffrn_reflns_theta_min 2.574 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_current 1.1 _diffrn_source_power 0.05500000000000001 _diffrn_source_type 'Incoatec I\ms DIAMOND' _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.851 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_correction_T_min 0.5635 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1372 before and 0.0754 after correction. The Ratio of minimum to maximum transmission is 0.7482. The \l/2 correction factor is Not present. ; _exptl_crystal_colour black _exptl_crystal_colour_primary black _exptl_crystal_density_diffrn 1.281 _exptl_crystal_description block _exptl_crystal_F_000 3416 _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.854 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.087 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.306 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 495 _refine_ls_number_reflns 4406 _refine_ls_number_restraints 150 _refine_ls_restrained_S_all 1.405 _refine_ls_R_factor_all 0.1381 _refine_ls_R_factor_gt 0.1054 _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 0.3007 _refine_ls_wR_factor_ref 0.3433 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2951 _reflns_number_total 4406 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5ee00031a2.cif _cod_data_source_block cu_240919lu_lgpz130690_2_0m _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_original_cell_volume 8412(2) _cod_database_code 1574096 _shelx_shelxl_version_number 2019/3 _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_max 0.783 _shelx_estimated_absorpt_t_min 0.708 _olex2_refinement_description ; 1. Restrained distances C17-C16 = C16-C15 = C17-C18 = C19-C18 = C19-C20 = C20-C21 = C21-C22 = C23-C22 = C24-C23 1.5 with sigma of 0.01 C44-C45 = C44-C43 = C43-C42 = C42-C41 = C40-C41 = C40-C35 = C35-C36 = C37-C36 = C38-C37 = C38-C39 1.5 with sigma of 0.01 C24-C22 = C23-C21 2.5 with sigma of 0.01 C22-C20 = C21-C19 2.5 with sigma of 0.01 C20-C18 = C19-C17 2.5 with sigma of 0.01 C18-C16 = C17-C15 2.5 with sigma of 0.01 C37-C39 = C38-C36 2.5 with sigma of 0.01 C37-C35 = C40-C36 2.5 with sigma of 0.01 C35-C41 = C42-C40 2.5 with sigma of 0.01 C41-C43 = C44-C42 2.5 with sigma of 0.01 C45-C43 2.5 with sigma of 0.01 2. Uiso/Uaniso restraints and constraints C34 \\sim C36 \\sim C35 \\sim C37 \\sim C40 \\sim C39 \\sim C38 \\sim C41 \\sim C42 \\sim C43 \\sim C44 \\sim C45: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A C16 \\sim C18 \\sim C17 \\sim C21 \\sim C20 \\sim C19 \\sim C22 \\sim C23 \\sim C24: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A 3.a Riding coordinates: C34(H34A,H34B) 3.b Ternary CH refined with riding coordinates: C35(H35) 3.c Secondary CH2 refined with riding coordinates: C16(H16A,H16B), C36(H36A,H36B), C41(H41A,H41B), C37(H37A,H37B), C22(H22A, H22B), C18(H18A,H18B), C40(H40A,H40B), C17(H17A,H17B), C23(H23A,H23B), C21(H21A,H21B), C20(H20A,H20B), C42(H42A,H42B), C19(H19A,H19B), C38(H38A,H38B), C43(H43A,H43B), C44(H44A,H44B) 3.d Aromatic/amide H refined with riding coordinates: C4(H4), C1(H1), C13(H13) 3.e Idealised Me refined as rotating group: C24(H24A,H24B,H24C), C39(H39A,H39B,H39C), C45(H45A,H45B,H45C) ; _shelx_res_file ; TITL cu_240919lu_lgpz130690_2_0m_a.res in C2/c cu_240919lu_lgpz130690_2_0m.res created by SHELXL-2019/3 at 11:21:50 on 19-Feb-2025 REM Old TITL cu_240919LU_LGPZ130690_2_0m in C2/c REM SHELXT solution in C2/c: R1 0.292, Rweak 0.020, Alpha 0.073 REM 0.369 for 180 systematic absences, Orientation as input REM Formula found by SHELXT: C72 N12 O2 S9 CELL 1.54178 29.1313 22.2253 14.0078 90 111.957 90 ZERR 4 0.0045 0.0037 0.0023 0 0.011 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H Cl N O S UNIT 360 376 16 32 8 20 DFIX 1.5 0.01 C17 C16 C16 C15 C17 C18 C19 C18 C19 C20 C20 C21 C21 C22 C23 = C22 C24 C23 DFIX 1.5 0.01 C44 C45 C44 C43 C43 C42 C42 C41 C40 C41 C40 C35 C35 C36 C37 = C36 C38 C37 C38 C39 DANG 2.5 0.01 C24 C22 C23 C21 DANG 2.5 0.01 C22 C20 C21 C19 DANG 2.5 0.01 C20 C18 C19 C17 DANG 2.5 0.01 C18 C16 C17 C15 DANG 2.5 0.01 C37 C39 C38 C36 DANG 2.5 0.01 C37 C35 C40 C36 DANG 2.5 0.01 C35 C41 C42 C40 DANG 2.5 0.01 C41 C43 C44 C42 DANG 2.5 0.01 C45 C43 SIMU 0.01 0.02 2 C34 C36 C35 C37 C40 C39 C38 C41 C42 C43 C44 C45 SIMU 0.01 0.02 2 C16 C18 C17 C21 C20 C19 C22 C23 C24 L.S. 20 PLAN 8 SIZE 0.09 0.11 0.13 TEMP -50.15 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta SIZE 0.09 0.11 0.13 SHEL 999 1 OMIT 5 1 0 REM REM REM WGHT 0.200000 FVAR 0.07201 S2 6 0.340364 0.412159 0.165593 11.00000 0.06479 0.09292 = 0.08756 -0.00064 0.02416 0.01753 S1 6 0.317316 0.225193 0.162504 11.00000 0.04311 0.09706 = 0.10672 -0.00062 0.01701 0.00692 S3 6 0.500000 0.560368 0.250000 10.50000 0.10715 0.07341 = 0.09154 0.00000 0.02956 0.00000 CL1 3 0.075764 -0.068786 0.042634 11.00000 0.08358 0.14618 = 0.09521 0.00202 0.02561 -0.02699 CL2 3 0.185599 -0.111888 0.095516 11.00000 0.11094 0.11985 = 0.13119 0.00593 0.04973 -0.00247 O1 5 0.274564 0.115589 0.140338 11.00000 0.05435 0.11892 = 0.14366 0.00610 0.03096 0.00163 N4 4 0.440813 0.289523 0.228139 11.00000 0.04909 0.07307 = 0.11720 -0.00166 0.03166 0.00085 C30 1 0.473644 0.447856 0.235361 11.00000 0.07183 0.07886 = 0.06675 -0.00061 0.02910 0.00445 C25 1 0.311921 0.341429 0.154510 11.00000 0.03892 0.10363 = 0.07764 -0.00676 0.00887 0.01634 C33 1 0.474319 0.335877 0.239721 11.00000 0.05537 0.08102 = 0.07674 0.00190 0.02773 -0.00669 C29 1 0.447951 0.392030 0.223267 11.00000 0.05982 0.07074 = 0.07506 0.00518 0.02789 0.01293 C5 1 0.149099 0.085965 0.078799 11.00000 0.05871 0.12898 = 0.06319 -0.00586 0.01005 -0.01600 C26 1 0.344944 0.294405 0.176094 11.00000 0.04547 0.08615 = 0.09455 -0.00325 0.02051 0.00176 C28 1 0.398076 0.377255 0.198453 11.00000 0.05776 0.08076 = 0.07448 0.00197 0.02041 0.01172 C6 1 0.147014 0.151064 0.071878 11.00000 0.04224 0.12678 = 0.07345 -0.00760 0.01036 -0.00468 C27 1 0.394238 0.315610 0.202054 11.00000 0.05251 0.08534 = 0.08685 0.00004 0.02637 0.00727 C9 1 0.197519 0.066419 0.104709 11.00000 0.05612 0.12506 = 0.07611 0.00830 0.01332 0.00596 C31 1 0.455229 0.506239 0.226576 11.00000 0.08327 0.07515 = 0.07328 0.00262 0.02826 0.00911 C4 1 0.111422 0.042951 0.060811 11.00000 0.07019 0.14335 = 0.06988 0.00342 0.02046 0.00380 AFIX 43 H4 2 0.078531 0.055243 0.045139 11.00000 -1.20000 AFIX 0 C10 1 0.105896 0.185650 0.046987 11.00000 0.03025 0.14335 = 0.11056 -0.02023 0.01100 0.00152 C3 1 0.123046 -0.017345 0.066315 11.00000 0.05507 0.13489 = 0.08094 -0.00043 0.02796 -0.01537 C15 1 0.263032 0.325445 0.125335 11.00000 0.06064 0.08995 = 0.09468 -0.00080 0.02026 0.01839 N3 4 0.367661 0.548818 0.181816 11.00000 0.11202 0.09810 = 0.14232 0.00963 0.05001 0.02910 C14 1 0.259392 0.261062 0.126548 11.00000 0.02877 0.14626 = 0.08681 -0.00714 0.00976 0.00969 C7 1 0.198570 0.172319 0.095938 11.00000 0.05950 0.13098 = 0.07698 0.00254 0.01676 0.00716 C8 1 0.229387 0.117581 0.117132 11.00000 0.04025 0.11388 = 0.09817 -0.00399 0.01664 -0.00909 C2 1 0.171632 -0.035967 0.091088 11.00000 0.09334 0.12673 = 0.07610 0.00236 0.03182 -0.01376 N1 4 0.019596 0.140185 0.013360 11.00000 0.04637 0.18228 = 0.18516 -0.01001 0.03961 -0.01456 N2 4 0.098433 0.300899 0.014074 11.00000 0.05465 0.13148 = 0.20034 -0.01160 0.02181 0.02130 C1 1 0.209772 0.005351 0.110742 11.00000 0.05448 0.12750 = 0.09508 0.00835 0.01854 -0.00232 AFIX 43 H1 2 0.242665 -0.007263 0.127510 11.00000 -1.20000 AFIX 0 C12 1 0.103148 0.249823 0.028363 11.00000 0.03025 0.14179 = 0.14518 -0.03500 0.01327 0.00955 C11 1 0.057933 0.159935 0.028238 11.00000 0.05590 0.15653 = 0.11857 -0.01332 0.03289 0.01406 C32 1 0.407115 0.527775 0.201946 11.00000 0.10807 0.07924 = 0.08661 0.00109 0.04123 0.00411 C13 1 0.213561 0.230280 0.100347 11.00000 0.05259 0.10614 = 0.09344 -0.00018 0.02106 0.01712 AFIX 43 H13 2 0.186675 0.257104 0.081076 11.00000 -1.20000 AFIX 0 C16 1 0.218796 0.364960 0.091533 11.00000 0.06373 0.11340 = 0.15211 -0.01125 0.03963 0.02684 AFIX 23 H16A 2 0.200686 0.357688 0.017943 11.00000 -1.20000 H16B 2 0.197398 0.351578 0.127241 11.00000 -1.20000 AFIX 0 C34 1 0.448733 0.225393 0.259303 11.00000 0.07587 0.08534 = 0.19778 0.02022 0.06897 0.00470 AFIX 3 H34A 2 0.461603 0.209783 0.208783 11.00000 -1.20000 H34B 2 0.412713 0.220343 0.229813 11.00000 -1.20000 AFIX 0 C36 1 0.430357 0.242821 0.419438 11.00000 0.15044 0.16228 = 0.18460 0.07959 0.05181 0.00343 AFIX 23 H36A 2 0.394988 0.234312 0.384295 11.00000 -1.20000 H36B 2 0.434901 0.285715 0.409335 11.00000 -1.20000 AFIX 0 C41 1 0.428705 0.101775 0.323947 11.00000 0.20485 0.09781 = 0.24967 0.04489 0.06249 -0.02037 AFIX 23 H41A 2 0.425014 0.107647 0.252105 11.00000 -1.20000 H41B 2 0.396526 0.109237 0.328958 11.00000 -1.20000 AFIX 0 C35 1 0.456195 0.209740 0.365473 11.00000 0.15600 0.10915 = 0.19885 0.04493 0.02177 0.00786 AFIX 13 H35 2 0.489967 0.226020 0.400932 11.00000 -1.20000 AFIX 0 C37 1 0.442453 0.233696 0.531446 11.00000 0.17404 0.20725 = 0.19132 0.06365 0.02476 -0.01078 AFIX 23 H37A 2 0.477982 0.240249 0.568569 11.00000 -1.20000 H37B 2 0.435085 0.191954 0.543214 11.00000 -1.20000 AFIX 0 C22 1 0.255190 0.671550 0.117355 11.00000 0.23554 0.23393 = 0.22503 0.02309 0.09653 0.03907 AFIX 23 H22A 2 0.272772 0.665532 0.070584 11.00000 -1.20000 H22B 2 0.276436 0.656377 0.185215 11.00000 -1.20000 AFIX 0 C18 1 0.178468 0.466146 0.056166 11.00000 0.14469 0.17422 = 0.25719 -0.00734 0.03936 0.04659 AFIX 23 H18A 2 0.167004 0.458954 -0.018135 11.00000 -1.20000 H18B 2 0.153425 0.449193 0.079562 11.00000 -1.20000 AFIX 0 C40 1 0.466051 0.145471 0.391200 11.00000 0.19242 0.10218 = 0.22685 0.04957 0.02788 -0.00954 AFIX 23 H40A 2 0.468547 0.139545 0.462300 11.00000 -1.20000 H40B 2 0.498358 0.135499 0.388734 11.00000 -1.20000 AFIX 0 C17 1 0.225174 0.430641 0.106221 11.00000 0.11239 0.15795 = 0.22267 -0.01161 0.03104 0.04069 AFIX 23 H17A 2 0.249680 0.444184 0.078388 11.00000 -1.20000 H17B 2 0.238426 0.439294 0.180187 11.00000 -1.20000 AFIX 0 C23 1 0.247242 0.737429 0.125727 11.00000 0.24212 0.24968 = 0.22001 0.02354 0.09975 0.03652 AFIX 23 H23A 2 0.229469 0.743810 0.172046 11.00000 -1.20000 H23B 2 0.226634 0.753135 0.057803 11.00000 -1.20000 AFIX 0 C21 1 0.208687 0.635559 0.079443 11.00000 0.22610 0.23149 = 0.24528 0.02499 0.08785 0.03672 AFIX 23 H21A 2 0.186471 0.651981 0.013388 11.00000 -1.20000 H21B 2 0.192084 0.639123 0.128477 11.00000 -1.20000 AFIX 0 C20 1 0.218263 0.569291 0.065711 11.00000 0.20689 0.22142 = 0.26397 0.01433 0.07714 0.02907 AFIX 23 H20A 2 0.221160 0.563781 -0.001223 11.00000 -1.20000 H20B 2 0.249813 0.557442 0.119191 11.00000 -1.20000 AFIX 0 C42 1 0.444734 0.037555 0.356165 11.00000 0.25376 0.11618 = 0.28395 0.02854 0.07791 -0.02711 AFIX 23 H42A 2 0.479692 0.033066 0.366107 11.00000 -1.20000 H42B 2 0.441613 0.029500 0.422259 11.00000 -1.20000 AFIX 0 C19 1 0.179069 0.530146 0.071442 11.00000 0.17851 0.21488 = 0.27470 0.00556 0.06554 0.02966 AFIX 23 H19A 2 0.177716 0.536489 0.139574 11.00000 -1.20000 H19B 2 0.147897 0.545649 0.021232 11.00000 -1.20000 AFIX 0 C24 1 0.295726 0.771763 0.166058 11.00000 0.26213 0.27981 = 0.24470 0.02925 0.09635 0.01515 AFIX 137 H24A 2 0.303414 0.786560 0.108600 11.00000 -1.50000 H24B 2 0.321976 0.745239 0.207929 11.00000 -1.50000 H24C 2 0.292799 0.805452 0.207442 11.00000 -1.50000 AFIX 0 C39 1 0.426353 0.273437 0.686372 11.00000 0.23111 0.31183 = 0.19653 0.02910 -0.01687 -0.04458 AFIX 137 H39A 2 0.398145 0.287603 0.700904 11.00000 -1.50000 H39B 2 0.454613 0.299217 0.720633 11.00000 -1.50000 H39C 2 0.434207 0.232528 0.711257 11.00000 -1.50000 AFIX 0 C38 1 0.414283 0.274909 0.573913 11.00000 0.18742 0.24055 = 0.19027 0.07660 0.03493 -0.00399 AFIX 23 H38A 2 0.419262 0.316165 0.555037 11.00000 -1.20000 H38B 2 0.378993 0.265730 0.539453 11.00000 -1.20000 AFIX 0 C43 1 0.414911 -0.007782 0.278967 11.00000 0.30642 0.13696 = 0.31429 0.01313 0.08200 -0.02700 AFIX 23 H43A 2 0.420696 -0.002726 0.214867 11.00000 -1.20000 H43B 2 0.379630 -0.001072 0.263799 11.00000 -1.20000 AFIX 0 C44 1 0.428732 -0.071572 0.319112 11.00000 0.34669 0.16351 = 0.33707 0.00531 0.07602 -0.03667 AFIX 23 H44A 2 0.462841 -0.079952 0.325902 11.00000 -1.20000 H44B 2 0.427083 -0.075035 0.387502 11.00000 -1.20000 AFIX 0 C45 1 0.394664 -0.117113 0.248236 11.00000 0.41316 0.19886 = 0.37641 -0.02627 0.07342 -0.07185 AFIX 137 H45A 2 0.404768 -0.124568 0.190706 11.00000 -1.50000 H45B 2 0.361040 -0.101823 0.222816 11.00000 -1.50000 H45C 2 0.396194 -0.154345 0.285436 11.00000 -1.50000 AFIX 0 HKLF 4 REM cu_240919lu_lgpz130690_2_0m_a.res in C2/c REM wR2 = 0.3433, GooF = S = 1.306, Restrained GooF = 1.405 for all data REM R1 = 0.1054 for 2951 Fo > 4sig(Fo) and 0.1381 for all 4406 data REM 495 parameters refined using 150 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 0.854, deepest hole -0.548, 1-sigma level 0.087 Q1 1 0.2088 0.3884 0.1841 11.00000 0.05 0.85 Q2 1 0.1607 0.4325 0.1432 11.00000 0.05 0.60 Q3 1 0.4285 0.2118 0.3772 11.00000 0.05 0.57 Q4 1 0.4574 0.2579 0.4646 11.00000 0.05 0.46 Q5 1 0.4470 0.2953 0.6181 11.00000 0.05 0.45 Q6 1 0.4780 0.1296 0.3235 11.00000 0.05 0.39 Q7 1 0.1771 0.5277 -0.0162 11.00000 0.05 0.35 Q8 1 0.1642 0.5837 0.0031 11.00000 0.05 0.35 ; _shelx_res_checksum 30809 _olex2_submission_special_instructions 'No special instructions were received' _site XU loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 S2 S 0.34036(8) 0.41216(10) 0.16559(16) 0.0830(8) Uani 1 1 d . . . . . S1 S 0.31732(7) 0.22519(10) 0.16250(18) 0.0855(8) Uani 1 1 d . . . . . S3 S 0.500000 0.56037(14) 0.250000 0.0929(11) Uani 1 2 d S T P . . Cl1 Cl 0.07576(9) -0.06879(13) 0.04263(18) 0.1106(10) Uani 1 1 d . . . . . Cl2 Cl 0.18560(11) -0.11189(13) 0.0955(2) 0.1194(10) Uani 1 1 d . . . . . O1 O 0.2746(2) 0.1156(3) 0.1403(5) 0.107(2) Uani 1 1 d . . . . . N4 N 0.4408(2) 0.2895(3) 0.2281(5) 0.0796(19) Uani 1 1 d . . . . . C30 C 0.4736(3) 0.4479(4) 0.2354(5) 0.072(2) Uani 1 1 d . . . . . C25 C 0.3119(3) 0.3414(4) 0.1545(6) 0.077(2) Uani 1 1 d . . . . . C33 C 0.4743(3) 0.3359(4) 0.2397(6) 0.070(2) Uani 1 1 d . . . . . C29 C 0.4480(3) 0.3920(3) 0.2233(5) 0.068(2) Uani 1 1 d . . . . . C5 C 0.1491(3) 0.0860(5) 0.0788(6) 0.087(3) Uani 1 1 d . . . . . C26 C 0.3449(3) 0.2944(4) 0.1761(6) 0.077(2) Uani 1 1 d . . . . . C28 C 0.3981(3) 0.3773(4) 0.1985(6) 0.072(2) Uani 1 1 d . . . . . C6 C 0.1470(3) 0.1511(5) 0.0719(6) 0.084(2) Uani 1 1 d . . . . . C27 C 0.3942(3) 0.3156(4) 0.2021(6) 0.075(2) Uani 1 1 d . . . . . C9 C 0.1975(3) 0.0664(5) 0.1047(6) 0.089(3) Uani 1 1 d . . . . . C31 C 0.4552(3) 0.5062(4) 0.2266(6) 0.078(2) Uani 1 1 d . . . . . C4 C 0.1114(4) 0.0430(6) 0.0608(6) 0.096(3) Uani 1 1 d . . . . . H4 H 0.078531 0.055243 0.045139 0.115 Uiso 1 1 calc R U . . . C10 C 0.1059(3) 0.1857(6) 0.0470(8) 0.099(3) Uani 1 1 d . . . . . C3 C 0.1230(3) -0.0173(5) 0.0663(7) 0.090(3) Uani 1 1 d . . . . . C15 C 0.2630(3) 0.3254(4) 0.1253(6) 0.084(2) Uani 1 1 d D . . . . N3 N 0.3677(4) 0.5488(4) 0.1818(7) 0.117(3) Uani 1 1 d . . . . . C14 C 0.2594(3) 0.2611(5) 0.1265(6) 0.091(3) Uani 1 1 d . . . . . C7 C 0.1986(3) 0.1723(5) 0.0959(6) 0.092(3) Uani 1 1 d . . . . . C8 C 0.2294(3) 0.1176(4) 0.1171(7) 0.087(2) Uani 1 1 d . . . . . C2 C 0.1716(4) -0.0360(5) 0.0911(7) 0.099(3) Uani 1 1 d . . . . . N1 N 0.0196(3) 0.1402(5) 0.0134(9) 0.139(4) Uani 1 1 d . . . . . N2 N 0.0984(3) 0.3009(6) 0.0141(9) 0.136(4) Uani 1 1 d . . . . . C1 C 0.2098(3) 0.0054(5) 0.1107(7) 0.095(3) Uani 1 1 d . . . . . H1 H 0.242665 -0.007263 0.127510 0.114 Uiso 1 1 calc R U . . . C12 C 0.1031(3) 0.2498(7) 0.0284(9) 0.111(4) Uani 1 1 d . . . . . C11 C 0.0579(4) 0.1599(6) 0.0282(8) 0.110(3) Uani 1 1 d . . . . . C32 C 0.4071(5) 0.5278(4) 0.2019(7) 0.090(3) Uani 1 1 d . . . . . C13 C 0.2136(3) 0.2303(5) 0.1003(7) 0.086(3) Uani 1 1 d . . . . . H13 H 0.186675 0.257104 0.081076 0.103 Uiso 1 1 calc R U . . . C16 C 0.2188(3) 0.3650(4) 0.0915(9) 0.110(3) Uani 1 1 d D U . . . H16A H 0.200686 0.357688 0.017943 0.132 Uiso 1 1 calc R U . . . H16B H 0.197398 0.351578 0.127241 0.132 Uiso 1 1 calc R U . . . C34 C 0.4487(4) 0.2254(4) 0.2593(10) 0.114(3) Uani 1 1 d . U . . . H34A H 0.461603 0.209783 0.208783 0.137 Uiso 1 1 d R U . . . H34B H 0.412713 0.220343 0.229813 0.137 Uiso 1 1 d R U . . . C36 C 0.4304(6) 0.2428(5) 0.4194(9) 0.169(4) Uani 1 1 d D U . . . H36A H 0.394988 0.234312 0.384295 0.203 Uiso 1 1 calc R U . . . H36B H 0.434901 0.285715 0.409335 0.203 Uiso 1 1 calc R U . . . C41 C 0.4287(6) 0.1018(4) 0.3239(12) 0.191(5) Uani 1 1 d D U . . . H41A H 0.425014 0.107647 0.252105 0.229 Uiso 1 1 calc R U . . . H41B H 0.396526 0.109237 0.328958 0.229 Uiso 1 1 calc R U . . . C35 C 0.4562(5) 0.2097(4) 0.3655(9) 0.168(4) Uani 1 1 d D U . . . H35 H 0.489967 0.226020 0.400932 0.201 Uiso 1 1 calc R U . . . C37 C 0.4425(6) 0.2337(8) 0.5314(9) 0.203(5) Uani 1 1 d D U . . . H37A H 0.477982 0.240249 0.568569 0.244 Uiso 1 1 calc R U . . . H37B H 0.435085 0.191954 0.543214 0.244 Uiso 1 1 calc R U . . . C22 C 0.2552(6) 0.6715(6) 0.1174(17) 0.228(6) Uani 1 1 d D U . . . H22A H 0.272772 0.665532 0.070584 0.274 Uiso 1 1 calc R U . . . H22B H 0.276436 0.656377 0.185215 0.274 Uiso 1 1 calc R U . . . C18 C 0.1785(4) 0.4661(4) 0.0562(14) 0.202(5) Uani 1 1 d D U . . . H18A H 0.167004 0.458954 -0.018135 0.243 Uiso 1 1 calc R U . . . H18B H 0.153425 0.449193 0.079562 0.243 Uiso 1 1 calc R U . . . C40 C 0.4661(5) 0.1455(4) 0.3912(11) 0.188(5) Uani 1 1 d D U . . . H40A H 0.468547 0.139545 0.462300 0.226 Uiso 1 1 calc R U . . . H40B H 0.498358 0.135499 0.388734 0.226 Uiso 1 1 calc R U . . . C17 C 0.2252(4) 0.4306(4) 0.1062(14) 0.173(4) Uani 1 1 d D U . . . H17A H 0.249680 0.444184 0.078388 0.208 Uiso 1 1 calc R U . . . H17B H 0.238426 0.439294 0.180187 0.208 Uiso 1 1 calc R U . . . C23 C 0.2472(7) 0.7374(6) 0.1257(18) 0.233(6) Uani 1 1 d D U . . . H23A H 0.229469 0.743810 0.172046 0.280 Uiso 1 1 calc R U . . . H23B H 0.226634 0.753135 0.057803 0.280 Uiso 1 1 calc R U . . . C21 C 0.2087(6) 0.6356(5) 0.0794(18) 0.234(6) Uani 1 1 d D U . . . H21A H 0.186471 0.651981 0.013388 0.281 Uiso 1 1 calc R U . . . H21B H 0.192084 0.639123 0.128477 0.281 Uiso 1 1 calc R U . . . C20 C 0.2183(7) 0.5693(6) 0.0657(18) 0.234(6) Uani 1 1 d D U . . . H20A H 0.221160 0.563781 -0.001223 0.281 Uiso 1 1 calc R U . . . H20B H 0.249813 0.557442 0.119191 0.281 Uiso 1 1 calc R U . . . C42 C 0.4447(7) 0.0376(4) 0.3562(13) 0.225(5) Uani 1 1 d D U . . . H42A H 0.479692 0.033066 0.366107 0.269 Uiso 1 1 calc R U . . . H42B H 0.441613 0.029500 0.422259 0.269 Uiso 1 1 calc R U . . . C19 C 0.1791(5) 0.5301(5) 0.0714(17) 0.228(5) Uani 1 1 d D U . . . H19A H 0.177716 0.536489 0.139574 0.274 Uiso 1 1 calc R U . . . H19B H 0.147897 0.545649 0.021232 0.274 Uiso 1 1 calc R U . . . C24 C 0.2957(8) 0.7718(8) 0.1661(18) 0.262(9) Uani 1 1 d D U . . . H24A H 0.303414 0.786560 0.108600 0.393 Uiso 1 1 calc R U . . . H24B H 0.321976 0.745239 0.207929 0.393 Uiso 1 1 calc R U . . . H24C H 0.292799 0.805452 0.207442 0.393 Uiso 1 1 calc R U . . . C39 C 0.4264(8) 0.2734(11) 0.6864(10) 0.275(10) Uani 1 1 d D U . . . H39A H 0.398145 0.287603 0.700904 0.412 Uiso 1 1 calc R U . . . H39B H 0.454613 0.299217 0.720633 0.412 Uiso 1 1 calc R U . . . H39C H 0.434207 0.232528 0.711257 0.412 Uiso 1 1 calc R U . . . C38 C 0.4143(7) 0.2749(8) 0.5739(10) 0.216(6) Uani 1 1 d D U . . . H38A H 0.419262 0.316165 0.555037 0.260 Uiso 1 1 calc R U . . . H38B H 0.378993 0.265730 0.539453 0.260 Uiso 1 1 calc R U . . . C43 C 0.4149(9) -0.0078(5) 0.2790(14) 0.262(6) Uani 1 1 d D U . . . H43A H 0.420696 -0.002726 0.214867 0.315 Uiso 1 1 calc R U . . . H43B H 0.379630 -0.001072 0.263799 0.315 Uiso 1 1 calc R U . . . C44 C 0.4287(10) -0.0716(5) 0.3191(17) 0.297(8) Uani 1 1 d D U . . . H44A H 0.462841 -0.079952 0.325902 0.357 Uiso 1 1 calc R U . . . H44B H 0.427083 -0.075035 0.387502 0.357 Uiso 1 1 calc R U . . . C45 C 0.3947(12) -0.1171(7) 0.248(2) 0.351(12) Uani 1 1 d D U . . . H45A H 0.404768 -0.124568 0.190706 0.526 Uiso 1 1 calc R U . . . H45B H 0.361040 -0.101823 0.222816 0.526 Uiso 1 1 calc R U . . . H45C H 0.396194 -0.154345 0.285436 0.526 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 S2 0.0648(15) 0.0929(15) 0.0876(14) -0.0006(11) 0.0242(11) 0.0175(11) S1 0.0431(13) 0.0971(16) 0.1067(16) -0.0006(11) 0.0170(11) 0.0069(10) S3 0.107(3) 0.0734(19) 0.092(2) 0.000 0.0296(19) 0.000 Cl1 0.0836(18) 0.146(2) 0.0952(17) 0.0020(14) 0.0256(13) -0.0270(15) Cl2 0.111(2) 0.120(2) 0.131(2) 0.0059(15) 0.0497(17) -0.0025(16) O1 0.054(4) 0.119(5) 0.144(5) 0.006(4) 0.031(4) 0.002(3) N4 0.049(4) 0.073(4) 0.117(5) -0.002(4) 0.032(4) 0.001(3) C30 0.072(5) 0.079(6) 0.067(5) -0.001(4) 0.029(4) 0.004(4) C25 0.039(5) 0.104(6) 0.078(5) -0.007(4) 0.009(4) 0.016(5) C33 0.055(4) 0.081(5) 0.077(5) 0.002(4) 0.028(4) -0.007(4) C29 0.060(6) 0.071(5) 0.075(5) 0.005(4) 0.028(4) 0.013(4) C5 0.059(6) 0.129(8) 0.063(5) -0.006(5) 0.010(4) -0.016(6) C26 0.045(5) 0.086(5) 0.095(6) -0.003(4) 0.021(4) 0.002(4) C28 0.058(6) 0.081(6) 0.074(5) 0.002(4) 0.020(4) 0.012(4) C6 0.042(6) 0.127(8) 0.073(5) -0.008(5) 0.010(4) -0.005(5) C27 0.053(6) 0.085(6) 0.087(5) 0.000(4) 0.026(4) 0.007(4) C9 0.056(6) 0.125(9) 0.076(5) 0.008(5) 0.013(4) 0.006(6) C31 0.083(6) 0.075(5) 0.073(5) 0.003(4) 0.028(4) 0.009(5) C4 0.070(6) 0.143(10) 0.070(5) 0.003(5) 0.020(5) 0.004(7) C10 0.030(5) 0.143(10) 0.111(7) -0.020(6) 0.011(4) 0.002(6) C3 0.055(6) 0.135(9) 0.081(6) 0.000(5) 0.028(5) -0.015(6) C15 0.061(7) 0.090(7) 0.095(6) -0.001(4) 0.020(5) 0.018(5) N3 0.112(7) 0.098(6) 0.142(7) 0.010(5) 0.050(6) 0.029(6) C14 0.029(5) 0.146(9) 0.087(5) -0.007(5) 0.010(4) 0.010(5) C7 0.059(6) 0.131(9) 0.077(5) 0.003(5) 0.017(4) 0.007(6) C8 0.040(5) 0.114(7) 0.098(6) -0.004(5) 0.017(4) -0.009(5) C2 0.093(8) 0.127(8) 0.076(5) 0.002(5) 0.032(5) -0.014(7) N1 0.046(6) 0.182(10) 0.185(9) -0.010(7) 0.040(6) -0.015(6) N2 0.055(5) 0.131(8) 0.200(11) -0.012(8) 0.022(6) 0.021(6) C1 0.054(6) 0.128(9) 0.095(6) 0.008(5) 0.019(5) -0.002(6) C12 0.030(5) 0.142(11) 0.145(9) -0.035(8) 0.013(5) 0.010(6) C11 0.056(8) 0.157(10) 0.119(8) -0.013(7) 0.033(6) 0.014(7) C32 0.108(9) 0.079(6) 0.087(6) 0.001(4) 0.041(6) 0.004(6) C13 0.053(6) 0.106(8) 0.093(6) 0.000(5) 0.021(4) 0.017(5) C16 0.064(5) 0.113(6) 0.152(7) -0.011(6) 0.040(5) 0.027(5) C34 0.076(6) 0.085(6) 0.198(9) 0.020(6) 0.069(6) 0.005(4) C36 0.150(8) 0.162(8) 0.185(8) 0.080(7) 0.052(7) 0.003(7) C41 0.205(9) 0.098(6) 0.250(10) 0.045(7) 0.062(8) -0.020(7) C35 0.156(7) 0.109(6) 0.199(8) 0.045(6) 0.022(6) 0.008(5) C37 0.174(10) 0.207(10) 0.191(9) 0.064(9) 0.025(8) -0.011(8) C22 0.236(12) 0.234(12) 0.225(11) 0.023(11) 0.097(10) 0.039(11) C18 0.145(8) 0.174(9) 0.257(10) -0.007(9) 0.039(8) 0.047(8) C40 0.192(9) 0.102(6) 0.227(9) 0.050(7) 0.028(8) -0.010(6) C17 0.112(7) 0.158(7) 0.223(9) -0.012(7) 0.031(7) 0.041(6) C23 0.242(14) 0.250(14) 0.220(12) 0.024(12) 0.100(11) 0.037(12) C21 0.226(12) 0.231(12) 0.245(11) 0.025(11) 0.088(10) 0.037(10) C20 0.207(11) 0.221(11) 0.264(11) 0.014(10) 0.077(10) 0.029(10) C42 0.254(11) 0.116(7) 0.284(11) 0.029(8) 0.078(9) -0.027(8) C19 0.179(10) 0.215(10) 0.275(10) 0.006(10) 0.066(9) 0.030(9) C24 0.26(2) 0.28(2) 0.245(17) 0.029(16) 0.096(16) 0.015(17) C39 0.231(17) 0.312(19) 0.197(14) 0.029(15) -0.017(14) -0.045(16) C38 0.187(12) 0.241(12) 0.190(10) 0.077(10) 0.035(9) -0.004(10) C43 0.306(13) 0.137(8) 0.314(13) 0.013(9) 0.082(11) -0.027(10) C44 0.347(15) 0.164(10) 0.337(15) 0.005(11) 0.076(13) -0.037(12) C45 0.41(2) 0.199(17) 0.38(2) -0.026(17) 0.07(2) -0.072(18) 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' 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' 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 C28 S2 C25 90.1(4) . . ? C26 S1 C14 89.2(5) . . ? C31 S3 C31 90.8(6) 2_655 . ? C33 N4 C27 107.2(6) . . ? C33 N4 C34 130.9(7) . . ? C27 N4 C34 120.4(7) . . ? C29 C30 C30 119.5(4) . 2_655 ? C31 C30 C30 111.2(5) . 2_655 ? C31 C30 C29 129.3(7) . . ? C26 C25 S2 113.1(6) . . ? C15 C25 S2 131.3(6) . . ? C15 C25 C26 115.5(8) . . ? N4 C33 C33 132.0(4) . 2_655 ? N4 C33 C29 108.4(6) . . ? C33 C33 C29 119.6(4) 2_655 . ? C30 C29 C33 120.7(7) . . ? C28 C29 C30 133.1(7) . . ? C28 C29 C33 106.2(7) . . ? C9 C5 C6 110.0(8) . . ? C9 C5 C4 118.9(10) . . ? C4 C5 C6 131.0(9) . . ? C25 C26 S1 113.4(6) . . ? C25 C26 C27 111.1(8) . . ? C27 C26 S1 135.5(7) . . ? C29 C28 S2 140.1(7) . . ? C27 C28 S2 111.6(6) . . ? C27 C28 C29 108.4(7) . . ? C5 C6 C7 106.8(8) . . ? C10 C6 C5 126.5(9) . . ? C10 C6 C7 126.8(10) . . ? N4 C27 C26 136.1(8) . . ? C28 C27 N4 109.8(7) . . ? C28 C27 C26 114.1(7) . . ? C5 C9 C8 109.4(9) . . ? C5 C9 C1 122.1(9) . . ? C1 C9 C8 128.5(9) . . ? C30 C31 S3 113.4(7) . . ? C30 C31 C32 131.2(8) . . ? C32 C31 S3 115.4(6) . . ? C5 C4 H4 120.2 . . ? C3 C4 C5 119.5(9) . . ? C3 C4 H4 120.2 . . ? C6 C10 C12 126.1(9) . . ? C6 C10 C11 121.7(11) . . ? C11 C10 C12 112.0(9) . . ? C4 C3 Cl1 118.2(8) . . ? C4 C3 C2 120.7(9) . . ? C2 C3 Cl1 121.1(9) . . ? C25 C15 C14 109.1(6) . . ? C25 C15 C16 128.5(8) . . ? C14 C15 C16 122.3(8) . . ? C15 C14 S1 112.8(6) . . ? C13 C14 S1 124.3(8) . . ? C13 C14 C15 122.9(8) . . ? C8 C7 C6 105.7(9) . . ? C13 C7 C6 126.4(9) . . ? C13 C7 C8 127.9(9) . . ? O1 C8 C9 125.5(9) . . ? O1 C8 C7 126.3(9) . . ? C9 C8 C7 108.1(8) . . ? C3 C2 Cl2 120.2(8) . . ? C1 C2 Cl2 118.5(9) . . ? C1 C2 C3 121.2(10) . . ? C9 C1 H1 121.2 . . ? C2 C1 C9 117.6(9) . . ? C2 C1 H1 121.2 . . ? N2 C12 C10 176.2(11) . . ? N1 C11 C10 179.2(13) . . ? N3 C32 C31 176.5(10) . . ? C14 C13 H13 111.7 . . ? C7 C13 C14 136.5(9) . . ? C7 C13 H13 111.7 . . ? C15 C16 H16A 107.5 . . ? C15 C16 H16B 107.5 . . ? H16A C16 H16B 107.0 . . ? C17 C16 C15 119.5(7) . . ? C17 C16 H16A 107.5 . . ? C17 C16 H16B 107.5 . . ? N4 C34 H34A 100.8 . . ? N4 C34 H34B 87.8 . . ? H34A C34 H34B 107.1 . . ? C35 C34 N4 118.4(9) . . ? C35 C34 H34A 134.3 . . ? C35 C34 H34B 97.5 . . ? H36A C36 H36B 106.8 . . ? C35 C36 H36A 107.1 . . ? C35 C36 H36B 107.1 . . ? C35 C36 C37 121.1(9) . . ? C37 C36 H36A 107.1 . . ? C37 C36 H36B 107.1 . . ? H41A C41 H41B 108.1 . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? C40 C41 C42 110.6(8) . . ? C42 C41 H41A 109.5 . . ? C42 C41 H41B 109.5 . . ? C34 C35 H35 99.5 . . ? C34 C35 C40 114.9(9) . . ? C36 C35 C34 120.0(9) . . ? C36 C35 H35 99.5 . . ? C36 C35 C40 117.1(9) . . ? C40 C35 H35 99.5 . . ? C36 C37 H37A 109.0 . . ? C36 C37 H37B 109.0 . . ? C36 C37 C38 112.8(9) . . ? H37A C37 H37B 107.8 . . ? C38 C37 H37A 109.0 . . ? C38 C37 H37B 109.0 . . ? H22A C22 H22B 107.6 . . ? C23 C22 H22A 108.7 . . ? C23 C22 H22B 108.7 . . ? C21 C22 H22A 108.7 . . ? C21 C22 H22B 108.7 . . ? C21 C22 C23 114.0(10) . . ? H18A C18 H18B 107.0 . . ? C17 C18 H18A 107.4 . . ? C17 C18 H18B 107.4 . . ? C19 C18 H18A 107.4 . . ? C19 C18 H18B 107.4 . . ? C19 C18 C17 119.5(9) . . ? C41 C40 H40A 108.2 . . ? C41 C40 H40B 108.2 . . ? C35 C40 C41 116.4(9) . . ? C35 C40 H40A 108.2 . . ? C35 C40 H40B 108.2 . . ? H40A C40 H40B 107.3 . . ? C16 C17 C18 114.2(8) . . ? C16 C17 H17A 108.7 . . ? C16 C17 H17B 108.7 . . ? C18 C17 H17A 108.7 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C22 C23 H23A 109.2 . . ? C22 C23 H23B 109.2 . . ? C22 C23 C24 111.9(10) . . ? H23A C23 H23B 107.9 . . ? C24 C23 H23A 109.2 . . ? C24 C23 H23B 109.2 . . ? C22 C21 H21A 109.2 . . ? C22 C21 H21B 109.2 . . ? C22 C21 C20 112.3(9) . . ? H21A C21 H21B 107.9 . . ? C20 C21 H21A 109.2 . . ? C20 C21 H21B 109.2 . . ? C21 C20 H20A 109.1 . . ? C21 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? C19 C20 C21 112.6(10) . . ? C19 C20 H20A 109.1 . . ? C19 C20 H20B 109.1 . . ? C41 C42 H42A 109.0 . . ? C41 C42 H42B 109.0 . . ? H42A C42 H42B 107.8 . . ? C43 C42 C41 112.8(9) . . ? C43 C42 H42A 109.0 . . ? C43 C42 H42B 109.0 . . ? C18 C19 C20 123.2(10) . . ? C18 C19 H19A 106.5 . . ? C18 C19 H19B 106.5 . . ? C20 C19 H19A 106.5 . . ? C20 C19 H19B 106.5 . . ? H19A C19 H19B 106.5 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? H39A C39 H39B 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? C37 C38 H38A 107.9 . . ? C37 C38 H38B 107.9 . . ? C39 C38 C37 117.6(10) . . ? C39 C38 H38A 107.9 . . ? C39 C38 H38B 107.9 . . ? H38A C38 H38B 107.2 . . ? C42 C43 H43A 109.4 . . ? C42 C43 H43B 109.4 . . ? C42 C43 C44 111.0(9) . . ? H43A C43 H43B 108.0 . . ? C44 C43 H43A 109.4 . . ? C44 C43 H43B 109.4 . . ? C43 C44 H44A 109.3 . . ? C43 C44 H44B 109.3 . . ? H44A C44 H44B 108.0 . . ? C45 C44 C43 111.4(10) . . ? C45 C44 H44A 109.3 . . ? C45 C44 H44B 109.3 . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45B 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? 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 S2 C25 1.757(9) . ? S2 C28 1.750(8) . ? S1 C26 1.713(9) . ? S1 C14 1.761(8) . ? S3 C31 1.713(9) . ? S3 C31 1.713(9) 2_655 ? Cl1 C3 1.724(10) . ? Cl2 C2 1.731(11) . ? O1 C8 1.233(10) . ? N4 C33 1.386(10) . ? N4 C27 1.393(10) . ? N4 C34 1.483(11) . ? C30 C30 1.434(16) 2_655 ? C30 C29 1.426(11) . ? C30 C31 1.392(11) . ? C25 C26 1.375(12) . ? C25 C15 1.373(11) . ? C33 C33 1.414(16) 2_655 ? C33 C29 1.438(11) . ? C29 C28 1.401(11) . ? C5 C6 1.450(14) . ? C5 C9 1.388(13) . ? C5 C4 1.405(14) . ? C26 C27 1.423(11) . ? C28 C27 1.377(12) . ? C6 C10 1.355(13) . ? C6 C7 1.488(13) . ? C9 C8 1.437(13) . ? C9 C1 1.398(14) . ? C31 C32 1.397(15) . ? C4 H4 0.9400 . ? C4 C3 1.377(14) . ? C10 C12 1.447(18) . ? C10 C11 1.440(16) . ? C3 C2 1.388(14) . ? C15 C14 1.435(13) . ? C15 C16 1.483(7) . ? N3 C32 1.173(13) . ? C14 C13 1.421(13) . ? C7 C8 1.475(14) . ? C7 C13 1.354(13) . ? C2 C1 1.387(14) . ? N1 C11 1.144(13) . ? N2 C12 1.152(16) . ? C1 H1 0.9400 . ? C13 H13 0.9400 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 C17 1.476(9) . ? C34 H34A 0.9799 . ? C34 H34B 0.9799 . ? C34 C35 1.462(16) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 C35 1.451(8) . ? C36 C37 1.488(9) . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 C40 1.499(9) . ? C41 C42 1.517(9) . ? C35 H35 0.9900 . ? C35 C40 1.475(8) . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 C38 1.494(9) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 C23 1.494(9) . ? C22 C21 1.490(10) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 C17 1.501(9) . ? C18 C19 1.438(8) . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 C24 1.516(10) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 C20 1.525(9) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 C19 1.461(9) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 C43 1.496(9) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C24 H24C 0.9700 . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C39 H39C 0.9700 . ? C39 C38 1.481(9) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 C44 1.523(10) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 C45 1.503(10) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C45 H45C 0.9700 . ? 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 S2 C25 C26 S1 -178.6(4) . . . . ? S2 C25 C26 C27 -0.1(9) . . . . ? S2 C25 C15 C14 178.4(6) . . . . ? S2 C25 C15 C16 1.5(14) . . . . ? S2 C28 C27 N4 179.9(5) . . . . ? S2 C28 C27 C26 1.5(9) . . . . ? S1 C26 C27 N4 -0.6(16) . . . . ? S1 C26 C27 C28 177.1(7) . . . . ? S1 C14 C13 C7 2.0(16) . . . . ? Cl1 C3 C2 Cl2 1.7(10) . . . . ? Cl1 C3 C2 C1 -179.6(7) . . . . ? Cl2 C2 C1 C9 178.7(7) . . . . ? N4 C33 C29 C30 176.9(6) . . . . ? N4 C33 C29 C28 -1.9(8) . . . . ? N4 C34 C35 C36 34.7(17) . . . . ? N4 C34 C35 C40 -177.3(9) . . . . ? C30 C30 C29 C33 -0.2(12) 2_655 . . . ? C30 C30 C29 C28 178.2(8) 2_655 . . . ? C30 C30 C31 S3 1.4(10) 2_655 . . . ? C30 C30 C31 C32 -178.8(9) 2_655 . . . ? C30 C29 C28 S2 2.4(15) . . . . ? C30 C29 C28 C27 -177.2(8) . . . . ? C25 S2 C28 C29 179.1(9) . . . . ? C25 S2 C28 C27 -1.3(6) . . . . ? C25 C26 C27 N4 -178.7(9) . . . . ? C25 C26 C27 C28 -1.0(10) . . . . ? C25 C15 C14 S1 -0.8(9) . . . . ? C25 C15 C14 C13 179.8(8) . . . . ? C25 C15 C16 C17 -12.3(18) . . . . ? C33 N4 C27 C26 177.0(9) . . . . ? C33 N4 C27 C28 -0.8(9) . . . . ? C33 N4 C34 C35 82.8(12) . . . . ? C33 C33 C29 C30 -4.9(12) 2_655 . . . ? C33 C33 C29 C28 176.3(9) 2_655 . . . ? C33 C29 C28 S2 -179.0(7) . . . . ? C33 C29 C28 C27 1.4(8) . . . . ? C29 C30 C31 S3 178.8(6) . . . . ? C29 C30 C31 C32 -1.4(14) . . . . ? C29 C28 C27 N4 -0.4(9) . . . . ? C29 C28 C27 C26 -178.8(6) . . . . ? C5 C6 C10 C12 -172.2(9) . . . . ? C5 C6 C10 C11 2.8(15) . . . . ? C5 C6 C7 C8 -0.4(9) . . . . ? C5 C6 C7 C13 -178.5(8) . . . . ? C5 C9 C8 O1 179.8(9) . . . . ? C5 C9 C8 C7 -0.9(10) . . . . ? C5 C9 C1 C2 -0.8(13) . . . . ? C5 C4 C3 Cl1 -179.4(6) . . . . ? C5 C4 C3 C2 1.1(13) . . . . ? C26 S1 C14 C15 0.4(7) . . . . ? C26 S1 C14 C13 179.9(8) . . . . ? C26 C25 C15 C14 0.8(11) . . . . ? C26 C25 C15 C16 -176.1(9) . . . . ? C28 S2 C25 C26 0.8(6) . . . . ? C28 S2 C25 C15 -176.9(8) . . . . ? C6 C5 C9 C8 0.7(10) . . . . ? C6 C5 C9 C1 -176.3(8) . . . . ? C6 C5 C4 C3 175.7(8) . . . . ? C6 C7 C8 O1 -180.0(9) . . . . ? C6 C7 C8 C9 0.8(9) . . . . ? C6 C7 C13 C14 175.6(9) . . . . ? C27 N4 C33 C33 -176.2(10) . . . 2_655 ? C27 N4 C33 C29 1.7(8) . . . . ? C27 N4 C34 C35 -81.3(12) . . . . ? C9 C5 C6 C10 179.1(8) . . . . ? C9 C5 C6 C7 -0.2(9) . . . . ? C9 C5 C4 C3 -1.9(12) . . . . ? C31 S3 C31 C30 -0.5(4) 2_655 . . . ? C31 S3 C31 C32 179.7(8) 2_655 . . . ? C31 C30 C29 C33 -177.5(7) . . . . ? C31 C30 C29 C28 0.9(14) . . . . ? C4 C5 C6 C10 1.4(15) . . . . ? C4 C5 C6 C7 -177.8(8) . . . . ? C4 C5 C9 C8 178.7(7) . . . . ? C4 C5 C9 C1 1.8(12) . . . . ? C4 C3 C2 Cl2 -178.9(7) . . . . ? C4 C3 C2 C1 -0.1(13) . . . . ? C10 C6 C7 C8 -179.6(9) . . . . ? C10 C6 C7 C13 2.3(14) . . . . ? C3 C2 C1 C9 0.0(13) . . . . ? C15 C25 C26 S1 -0.5(10) . . . . ? C15 C25 C26 C27 178.0(7) . . . . ? C15 C14 C13 C7 -178.6(10) . . . . ? C15 C16 C17 C18 172.1(13) . . . . ? C14 S1 C26 C25 0.0(7) . . . . ? C14 S1 C26 C27 -178.0(9) . . . . ? C14 C15 C16 C17 171.2(12) . . . . ? C7 C6 C10 C12 6.9(16) . . . . ? C7 C6 C10 C11 -178.1(9) . . . . ? C8 C9 C1 C2 -177.1(8) . . . . ? C8 C7 C13 C14 -2.0(17) . . . . ? C1 C9 C8 O1 -3.5(16) . . . . ? C1 C9 C8 C7 175.7(8) . . . . ? C13 C7 C8 O1 -1.9(16) . . . . ? C13 C7 C8 C9 178.8(9) . . . . ? C16 C15 C14 S1 176.4(7) . . . . ? C16 C15 C14 C13 -3.1(14) . . . . ? C34 N4 C33 C33 18.2(17) . . . 2_655 ? C34 N4 C33 C29 -163.9(9) . . . . ? C34 N4 C27 C26 -15.6(15) . . . . ? C34 N4 C27 C28 166.6(8) . . . . ? C34 C35 C40 C41 -54.8(18) . . . . ? C36 C35 C40 C41 94.1(18) . . . . ? C36 C37 C38 C39 -175.0(17) . . . . ? C41 C42 C43 C44 -174(2) . . . . ? C35 C36 C37 C38 176.0(15) . . . . ? C37 C36 C35 C34 -171.4(14) . . . . ? C37 C36 C35 C40 41(2) . . . . ? C22 C21 C20 C19 156(2) . . . . ? C40 C41 C42 C43 -167.7(19) . . . . ? C17 C18 C19 C20 44(3) . . . . ? C23 C22 C21 C20 176.4(19) . . . . ? C21 C22 C23 C24 179(2) . . . . ? C21 C20 C19 C18 177.1(18) . . . . ? C42 C41 C40 C35 177.4(14) . . . . ? C42 C43 C44 C45 173(3) . . . . ? C19 C18 C17 C16 175.3(16) . . . . ?