#------------------------------------------------------------------------------ #$Date: 2020-09-24 06:42:34 +0300 (Thu, 24 Sep 2020) $ #$Revision: 256705 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/91/1559177.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_1559177 loop_ _publ_author_name 'Yoshino, Junro' 'Hirono, Yoshito' 'Akahane, Ryota' 'Higuchi, Hiroyuki' 'Hayashi, Naoto' _publ_section_title ; Effects of \p-Conjugation on the Solid-State Photoresponsive Coloring Behavior of Bipyridine-Boronium Complexes ; _journal_name_full 'Photochemical & Photobiological Sciences' _journal_paper_doi 10.1039/D0PP00296H _journal_year 2020 _chemical_formula_moiety 'C30 H30 B1 N2 1+, C1 F3 O3 S1 1-, C1 H1 Cl3' _chemical_formula_sum 'C32 H31 B Cl3 F3 N2 O3 S' _chemical_formula_weight 697.83 _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 geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_update_record ; 2019-08-29 deposited with the CCDC. 2020-09-23 downloaded from the CCDC. ; _cell_angle_alpha 90.0000 _cell_angle_beta 101.544(7) _cell_angle_gamma 90.0000 _cell_formula_units_Z 8 _cell_length_a 14.5487(3) _cell_length_b 15.4322(3) _cell_length_c 28.7510(6) _cell_measurement_reflns_used 23931 _cell_measurement_temperature 173 _cell_measurement_theta_max 27.47 _cell_measurement_theta_min 1.95 _cell_volume 6324.6(3) _computing_cell_refinement 'RAPID AUTO' _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_data_reduction 'RAPID AUTO' _computing_molecular_graphics 'CrystalStructure 4.2' _computing_publication_material 'CrystalStructure 4.2 (Rigaku, 2017)' _computing_structure_refinement 'SHELXL Version 2018/1 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS Version 2013/1 (Sheldrick, 2008)' _diffrn_ambient_temperature 173 _diffrn_detector_area_resol_mean 10.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_number 30627 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.466 _diffrn_reflns_theta_min 1.945 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.411 _exptl_absorpt_correction_T_max 0.867 _exptl_absorpt_correction_T_min 0.718 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 2880.00 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Chloroform' _exptl_crystal_size_max 0.444 _exptl_crystal_size_mid 0.418 _exptl_crystal_size_min 0.348 _refine_diff_density_max 0.52 _refine_diff_density_min -0.53 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 406 _refine_ls_number_reflns 7236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0604 _refine_ls_R_factor_gt 0.0457 _refine_ls_shift/su_max 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0575P)^2^+8.1764P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1131 _refine_ls_wR_factor_ref 0.1210 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5829 _reflns_number_total 7236 _reflns_threshold_expression F^2^>2.0\s(F^2^) _cod_data_source_file d0pp00296h2.cif _cod_data_source_block dp4bpybbnotf _cod_original_cell_volume 6324.5(3) _cod_database_code 1559177 _shelx_res_file ; TITL dp4bpybbnotf shelxl.res created by SHELXL-2018/1 at 09:16:44 on 27-Feb-2018 CELL 0.71075 14.54874 15.43218 28.75095 90.00000 101.54430 90.00000 ZERR 8 0.00031 0.00033 0.00061 0.00000 0.00710 0.00000 LATT 7 SYMM -X, +Y, .50-Z SFAC C H B F N O S CL UNIT 256 248 8 24 16 24 8 24 L.S. 5 FMAP 2 PLAN 51 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP -100.0 ACTA SIZE 0.444 0.418 0.348 WGHT 0.057500 8.176399 FVAR 0.34812 CL1 8 0.473895 0.120422 0.461821 11.00000 0.09138 0.08045 = 0.08735 -0.00892 0.05050 -0.01585 CL2 8 0.548227 0.290434 0.451421 11.00000 0.13243 0.04882 = 0.06463 0.00631 0.03143 0.01664 CL3 8 0.671835 0.153828 0.492285 11.00000 0.09057 0.09855 = 0.05612 -0.01011 -0.00691 0.02578 S1 7 0.679298 0.051704 0.342027 11.00000 0.03717 0.02511 = 0.02664 -0.00155 0.01247 -0.00401 F1 4 0.773263 0.018772 0.427801 11.00000 0.05441 0.07780 = 0.04105 0.00106 -0.00434 -0.00080 F2 4 0.730130 -0.094392 0.385897 11.00000 0.09422 0.03679 = 0.05840 0.00974 0.02285 0.01767 F3 4 0.630356 -0.021219 0.415783 11.00000 0.05991 0.06707 = 0.04985 0.01830 0.02923 -0.00253 O1 6 0.654086 0.134427 0.358991 11.00000 0.05308 0.02794 = 0.03481 -0.00156 0.01732 0.00128 O2 6 0.604026 0.005915 0.312208 11.00000 0.05289 0.03828 = 0.04174 -0.00543 0.00029 -0.00880 O3 6 0.766988 0.050521 0.326104 11.00000 0.05316 0.04144 = 0.05032 -0.00095 0.03304 -0.00312 N1 5 0.893982 0.014144 0.164350 11.00000 0.02879 0.02800 = 0.01954 -0.00002 0.00755 -0.00004 N2 5 0.885533 0.166262 0.174260 11.00000 0.02482 0.02755 = 0.01917 0.00109 0.00458 -0.00235 C1 1 0.902592 -0.069823 0.153221 11.00000 0.03966 0.03259 = 0.02320 -0.00425 0.01146 0.00224 AFIX 43 H1 2 0.913000 -0.083996 0.122537 11.00000 -1.20000 AFIX 0 C2 1 0.896880 -0.135635 0.184585 11.00000 0.03490 0.02697 = 0.02916 -0.00425 0.01019 0.00208 AFIX 43 H2 2 0.904542 -0.193891 0.175381 11.00000 -1.20000 AFIX 0 C3 1 0.879888 -0.118330 0.230093 11.00000 0.02129 0.02765 = 0.02455 -0.00040 0.00472 -0.00092 C4 1 0.869821 -0.030993 0.241164 11.00000 0.02653 0.02714 = 0.02191 -0.00215 0.00682 -0.00148 AFIX 43 H4 2 0.857098 -0.015237 0.271188 11.00000 -1.20000 AFIX 0 C5 1 0.878423 0.032121 0.208368 11.00000 0.02154 0.02719 = 0.02017 -0.00270 0.00488 -0.00089 C6 1 0.875218 0.125569 0.214834 11.00000 0.02132 0.02608 = 0.02047 0.00137 0.00547 -0.00189 C7 1 0.866791 0.169338 0.255649 11.00000 0.02570 0.02626 = 0.02026 0.00008 0.00634 -0.00235 AFIX 43 H7 2 0.859116 0.138179 0.283114 11.00000 -1.20000 AFIX 0 C8 1 0.869644 0.259902 0.256233 11.00000 0.02078 0.02647 = 0.02412 -0.00101 0.00426 -0.00225 C9 1 0.879058 0.300967 0.213902 11.00000 0.03219 0.02388 = 0.02910 0.00197 0.00569 -0.00232 AFIX 43 H9 2 0.880108 0.362459 0.212543 11.00000 -1.20000 AFIX 0 C10 1 0.886780 0.253678 0.174393 11.00000 0.03311 0.02993 = 0.02383 0.00577 0.00655 -0.00332 AFIX 43 H10 2 0.893196 0.283442 0.146295 11.00000 -1.20000 AFIX 0 C11 1 0.875600 -0.188278 0.264908 11.00000 0.02224 0.02831 = 0.02843 0.00132 0.00521 0.00043 C12 1 0.887586 -0.274762 0.253388 11.00000 0.04330 0.02962 = 0.03279 -0.00056 0.00812 0.00197 AFIX 43 H12 2 0.895589 -0.289177 0.222321 11.00000 -1.20000 AFIX 0 C13 1 0.888005 -0.339811 0.286441 11.00000 0.05740 0.02743 = 0.04813 0.00570 0.01355 0.00517 AFIX 43 H13 2 0.896402 -0.398375 0.277999 11.00000 -1.20000 AFIX 0 C14 1 0.876223 -0.319887 0.331827 11.00000 0.04512 0.03869 = 0.04722 0.01786 0.01691 0.00901 AFIX 43 H14 2 0.876991 -0.364508 0.354665 11.00000 -1.20000 AFIX 0 C15 1 0.863314 -0.234425 0.343667 11.00000 0.04785 0.04362 = 0.03737 0.01121 0.02122 0.00934 AFIX 43 H15 2 0.855000 -0.220496 0.374746 11.00000 -1.20000 AFIX 0 C16 1 0.862421 -0.169206 0.310642 11.00000 0.04091 0.03121 = 0.03486 0.00485 0.01697 0.00625 AFIX 43 H16 2 0.852765 -0.110889 0.319103 11.00000 -1.20000 AFIX 0 C17 1 0.865040 0.309443 0.299695 11.00000 0.02287 0.02450 = 0.02579 -0.00234 0.00307 0.00162 C18 1 0.821258 0.274725 0.334487 11.00000 0.02569 0.02952 = 0.02796 -0.00210 0.00446 -0.00141 AFIX 43 H18 2 0.792258 0.219399 0.329765 11.00000 -1.20000 AFIX 0 C19 1 0.819742 0.320271 0.375841 11.00000 0.03197 0.03882 = 0.02937 -0.00338 0.00937 0.00283 AFIX 43 H19 2 0.788633 0.296639 0.399016 11.00000 -1.20000 AFIX 0 C20 1 0.863593 0.400395 0.383499 11.00000 0.03991 0.03669 = 0.03338 -0.01285 0.00527 0.00595 AFIX 43 H20 2 0.863449 0.431119 0.412118 11.00000 -1.20000 AFIX 0 C21 1 0.907560 0.435432 0.349301 11.00000 0.03966 0.02573 = 0.04381 -0.01044 0.00708 -0.00013 AFIX 43 H21 2 0.937979 0.490050 0.354593 11.00000 -1.20000 AFIX 0 C22 1 0.907248 0.390952 0.307388 11.00000 0.03410 0.02527 = 0.03579 -0.00204 0.00933 -0.00031 AFIX 43 H22 2 0.935954 0.416068 0.283696 11.00000 -1.20000 AFIX 0 C23 1 0.983468 0.113537 0.108357 11.00000 0.02386 0.04766 = 0.02280 0.00078 0.00526 -0.00336 AFIX 13 H23 2 1.041101 0.112815 0.134021 11.00000 -1.20000 AFIX 0 C24 1 0.990105 0.039373 0.073206 11.00000 0.03823 0.05145 = 0.03011 0.00041 0.01767 0.00282 AFIX 23 H24A 2 1.042216 0.052169 0.056780 11.00000 -1.20000 H24B 2 1.005957 -0.014862 0.091438 11.00000 -1.20000 AFIX 0 C25 1 0.900393 0.024238 0.035634 11.00000 0.05240 0.04667 = 0.02452 -0.00560 0.01398 -0.00031 AFIX 23 H25A 2 0.904829 -0.033345 0.021066 11.00000 -1.20000 H25B 2 0.897714 0.068183 0.010312 11.00000 -1.20000 AFIX 0 C26 1 0.808105 0.028205 0.053943 11.00000 0.03790 0.04339 = 0.02401 -0.00405 0.00313 -0.00610 AFIX 23 H26A 2 0.799436 -0.027751 0.069348 11.00000 -1.20000 H26B 2 0.755597 0.034757 0.026364 11.00000 -1.20000 AFIX 0 C27 1 0.801789 0.101947 0.089524 11.00000 0.02441 0.03862 = 0.02225 -0.00040 0.00569 -0.00364 AFIX 13 H27 2 0.744818 0.092303 0.103379 11.00000 -1.20000 AFIX 0 C28 1 0.794281 0.191753 0.066005 11.00000 0.03548 0.04240 = 0.02547 0.00304 0.00017 0.00193 AFIX 23 H28A 2 0.741687 0.190722 0.038197 11.00000 -1.20000 H28B 2 0.778412 0.234579 0.088798 11.00000 -1.20000 AFIX 0 C29 1 0.882724 0.222871 0.049544 11.00000 0.04974 0.04114 = 0.02948 0.00893 0.00695 -0.00512 AFIX 23 H29A 2 0.878231 0.286429 0.044981 11.00000 -1.20000 H29B 2 0.883414 0.196511 0.018224 11.00000 -1.20000 AFIX 0 C30 1 0.976823 0.202300 0.083000 11.00000 0.03640 0.04892 = 0.02966 0.00072 0.01322 -0.01322 AFIX 23 H30A 2 0.989531 0.248189 0.107510 11.00000 -1.20000 H30B 2 1.027086 0.205289 0.064382 11.00000 -1.20000 AFIX 0 C31 1 0.704778 -0.014168 0.395723 11.00000 0.04100 0.03736 = 0.03393 0.00283 0.01244 0.00137 C32 1 0.570588 0.178825 0.450682 11.00000 0.06525 0.04846 = 0.03449 -0.00199 0.01757 0.00565 AFIX 13 H32 2 0.580964 0.162763 0.418432 11.00000 -1.20000 AFIX 0 B1 3 0.893164 0.099410 0.131964 11.00000 0.02888 0.02834 = 0.01913 -0.00002 0.00656 -0.00119 HKLF 4 REM dp4bpybbnotf REM R1 = 0.0457 for 5829 Fo > 4sig(Fo) and 0.0604 for all 7236 data REM 406 parameters refined using 0 restraints END WGHT 0.0480 9.0812 REM Instructions for potential hydrogen bonds HTAB C4 O3 HTAB C7 O3 EQIV $1 -x+3/2, y+1/2, -z+1/2 HTAB C9 O2_$1 HTAB C10 F2_$1 HTAB C32 O1 REM Highest difference peak 0.516, deepest hole -0.533, 1-sigma level 0.051 Q1 1 0.6580 0.2061 0.4795 11.00000 0.05 0.52 Q2 1 0.5229 0.1061 0.4861 11.00000 0.05 0.47 Q3 1 0.4948 0.3129 0.4369 11.00000 0.05 0.38 Q4 1 0.6969 0.0170 0.3700 11.00000 0.05 0.37 Q5 1 0.8801 -0.1551 0.2492 11.00000 0.05 0.33 Q6 1 0.5843 0.2736 0.4322 11.00000 0.05 0.33 Q7 1 0.7721 -0.0637 0.4012 11.00000 0.05 0.30 Q8 1 0.8658 0.2841 0.2778 11.00000 0.05 0.29 Q9 1 0.9388 0.1109 0.1206 11.00000 0.05 0.28 Q10 1 0.9023 0.0506 0.1479 11.00000 0.05 0.27 Q11 1 0.8833 -0.0740 0.2377 11.00000 0.05 0.26 Q12 1 0.7938 0.0742 0.4329 11.00000 0.05 0.25 Q13 1 0.8785 -0.1740 0.2869 11.00000 0.05 0.25 Q14 1 0.8049 0.0626 0.0717 11.00000 0.05 0.25 Q15 1 0.8600 0.1466 0.2329 11.00000 0.05 0.24 Q16 1 0.8411 0.1041 0.1119 11.00000 0.05 0.24 Q17 1 0.7214 0.1599 0.5008 11.00000 0.05 0.24 Q18 1 0.8970 -0.1274 0.2098 11.00000 0.05 0.24 Q19 1 0.8503 -0.2067 0.3242 11.00000 0.05 0.24 Q20 1 0.8478 0.2145 0.2505 11.00000 0.05 0.24 Q21 1 0.9033 0.2730 0.1985 11.00000 0.05 0.24 Q22 1 0.8680 0.0777 0.2100 11.00000 0.05 0.23 Q23 1 0.7462 0.0411 0.3402 11.00000 0.05 0.23 Q24 1 0.8459 0.2917 0.3163 11.00000 0.05 0.23 Q25 1 0.9261 0.2069 0.0655 11.00000 0.05 0.23 Q26 1 0.8577 0.0274 0.0476 11.00000 0.05 0.23 Q27 1 0.8824 0.2795 0.2363 11.00000 0.05 0.22 Q28 1 0.8787 -0.2309 0.2605 11.00000 0.05 0.22 Q29 1 0.8418 0.2124 0.0607 11.00000 0.05 0.22 Q30 1 0.8955 -0.3206 0.3110 11.00000 0.05 0.22 Q31 1 0.8930 0.1345 0.1549 11.00000 0.05 0.22 Q32 1 0.5150 0.2460 0.4604 11.00000 0.05 0.22 Q33 1 0.9046 0.4098 0.3289 11.00000 0.05 0.22 Q34 1 0.8738 0.3521 0.3014 11.00000 0.05 0.21 Q35 1 0.9010 -0.0258 0.1612 11.00000 0.05 0.21 Q36 1 0.9221 0.3993 0.3355 11.00000 0.05 0.21 Q37 1 0.8973 0.1446 0.1994 11.00000 0.05 0.21 Q38 1 0.8973 0.4052 0.3703 11.00000 0.05 0.21 Q39 1 0.6127 0.0424 0.3213 11.00000 0.05 0.21 Q40 1 0.8000 0.1464 0.0790 11.00000 0.05 0.21 Q41 1 0.6737 0.1021 0.3543 11.00000 0.05 0.20 Q42 1 0.8617 0.3513 0.3855 11.00000 0.05 0.20 Q43 1 0.8142 0.3043 0.3518 11.00000 0.05 0.20 Q44 1 0.9210 -0.0956 0.1767 11.00000 0.05 0.20 Q45 1 0.9823 0.0742 0.0910 11.00000 0.05 0.20 Q46 1 0.9020 0.2060 0.1787 11.00000 0.05 0.20 Q47 1 0.6291 -0.0698 0.3997 11.00000 0.05 0.20 Q48 1 0.9431 0.0351 0.0583 11.00000 0.05 0.19 Q49 1 0.8621 0.0000 0.2216 11.00000 0.05 0.19 Q50 1 0.8907 0.0203 0.1901 11.00000 0.05 0.19 Q51 1 0.8524 -0.2801 0.3318 11.00000 0.05 0.19 ; _shelx_res_checksum 13029 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 Cl1 Cl 0.47389(7) 0.12042(6) 0.46182(3) 0.0819(3) Uani 1 1 d . . . . . Cl2 Cl 0.54823(7) 0.29043(5) 0.45142(3) 0.0803(3) Uani 1 1 d . . . . . Cl3 Cl 0.67183(7) 0.15383(7) 0.49229(3) 0.0847(3) Uani 1 1 d . . . . . S1 S 0.67930(3) 0.05170(3) 0.34203(2) 0.02880(12) Uani 1 1 d . . . . . F1 F 0.77326(11) 0.01877(11) 0.42780(5) 0.0597(4) Uani 1 1 d . . . . . F2 F 0.73013(13) -0.09439(9) 0.38590(5) 0.0621(4) Uani 1 1 d . . . . . F3 F 0.63036(11) -0.02122(10) 0.41578(5) 0.0564(4) Uani 1 1 d . . . . . O1 O 0.65409(11) 0.13443(9) 0.35899(5) 0.0374(3) Uani 1 1 d . . . . . O2 O 0.60403(12) 0.00591(10) 0.31221(6) 0.0456(4) Uani 1 1 d . . . . . O3 O 0.76699(12) 0.05052(10) 0.32610(6) 0.0452(4) Uani 1 1 d . . . . . N1 N 0.89398(10) 0.01414(10) 0.16435(5) 0.0251(3) Uani 1 1 d . . . . . N2 N 0.88553(10) 0.16626(10) 0.17426(5) 0.0238(3) Uani 1 1 d . . . . . C1 C 0.90259(14) -0.06982(13) 0.15322(6) 0.0311(4) Uani 1 1 d . . . . . H1 H 0.913000 -0.083996 0.122537 0.037 Uiso 1 1 calc R U . . . C2 C 0.89688(14) -0.13563(12) 0.18459(7) 0.0298(4) Uani 1 1 d . . . . . H2 H 0.904542 -0.193891 0.175381 0.036 Uiso 1 1 calc R U . . . C3 C 0.87989(12) -0.11833(11) 0.23009(6) 0.0245(3) Uani 1 1 d . . . . . C4 C 0.86982(12) -0.03099(11) 0.24116(6) 0.0249(4) Uani 1 1 d . . . . . H4 H 0.857098 -0.015237 0.271188 0.030 Uiso 1 1 calc R U . . . C5 C 0.87842(12) 0.03212(11) 0.20837(6) 0.0229(3) Uani 1 1 d . . . . . C6 C 0.87522(12) 0.12557(11) 0.21483(6) 0.0224(3) Uani 1 1 d . . . . . C7 C 0.86679(12) 0.16934(11) 0.25565(6) 0.0238(3) Uani 1 1 d . . . . . H7 H 0.859116 0.138179 0.283114 0.029 Uiso 1 1 calc R U . . . C8 C 0.86964(12) 0.25990(11) 0.25623(6) 0.0238(3) Uani 1 1 d . . . . . C9 C 0.87906(13) 0.30097(12) 0.21390(6) 0.0285(4) Uani 1 1 d . . . . . H9 H 0.880108 0.362459 0.212543 0.034 Uiso 1 1 calc R U . . . C10 C 0.88678(13) 0.25368(12) 0.17439(6) 0.0288(4) Uani 1 1 d . . . . . H10 H 0.893196 0.283442 0.146295 0.035 Uiso 1 1 calc R U . . . C11 C 0.87560(12) -0.18828(12) 0.26491(6) 0.0263(4) Uani 1 1 d . . . . . C12 C 0.88759(15) -0.27476(13) 0.25339(7) 0.0352(4) Uani 1 1 d . . . . . H12 H 0.895589 -0.289177 0.222321 0.042 Uiso 1 1 calc R U . . . C13 C 0.88801(17) -0.33981(14) 0.28644(8) 0.0439(5) Uani 1 1 d . . . . . H13 H 0.896402 -0.398375 0.277999 0.053 Uiso 1 1 calc R U . . . C14 C 0.87622(16) -0.31989(14) 0.33183(8) 0.0426(5) Uani 1 1 d . . . . . H14 H 0.876991 -0.364508 0.354665 0.051 Uiso 1 1 calc R U . . . C15 C 0.86331(16) -0.23443(14) 0.34367(8) 0.0412(5) Uani 1 1 d . . . . . H15 H 0.855000 -0.220496 0.374746 0.049 Uiso 1 1 calc R U . . . C16 C 0.86242(15) -0.16921(13) 0.31064(7) 0.0344(4) Uani 1 1 d . . . . . H16 H 0.852765 -0.110889 0.319103 0.041 Uiso 1 1 calc R U . . . C17 C 0.86504(12) 0.30944(11) 0.29970(6) 0.0246(4) Uani 1 1 d . . . . . C18 C 0.82126(13) 0.27473(12) 0.33449(6) 0.0279(4) Uani 1 1 d . . . . . H18 H 0.792258 0.219399 0.329765 0.033 Uiso 1 1 calc R U . . . C19 C 0.81974(14) 0.32027(13) 0.37584(7) 0.0329(4) Uani 1 1 d . . . . . H19 H 0.788633 0.296639 0.399016 0.040 Uiso 1 1 calc R U . . . C20 C 0.86359(15) 0.40040(14) 0.38350(7) 0.0369(5) Uani 1 1 d . . . . . H20 H 0.863449 0.431119 0.412118 0.044 Uiso 1 1 calc R U . . . C21 C 0.90756(15) 0.43543(13) 0.34930(8) 0.0366(4) Uani 1 1 d . . . . . H21 H 0.937979 0.490050 0.354593 0.044 Uiso 1 1 calc R U . . . C22 C 0.90725(14) 0.39095(12) 0.30739(7) 0.0314(4) Uani 1 1 d . . . . . H22 H 0.935954 0.416068 0.283696 0.038 Uiso 1 1 calc R U . . . C23 C 0.98347(13) 0.11354(14) 0.10836(6) 0.0314(4) Uani 1 1 d . . . . . H23 H 1.041101 0.112815 0.134021 0.038 Uiso 1 1 calc R U . . . C24 C 0.99011(15) 0.03937(15) 0.07321(7) 0.0384(5) Uani 1 1 d . . . . . H24A H 1.042216 0.052169 0.056780 0.046 Uiso 1 1 calc R U . . . H24B H 1.005957 -0.014862 0.091438 0.046 Uiso 1 1 calc R U . . . C25 C 0.90039(16) 0.02424(15) 0.03563(7) 0.0403(5) Uani 1 1 d . . . . . H25A H 0.904829 -0.033345 0.021066 0.048 Uiso 1 1 calc R U . . . H25B H 0.897714 0.068183 0.010312 0.048 Uiso 1 1 calc R U . . . C26 C 0.80811(15) 0.02821(14) 0.05394(7) 0.0355(4) Uani 1 1 d . . . . . H26A H 0.799436 -0.027751 0.069348 0.043 Uiso 1 1 calc R U . . . H26B H 0.755597 0.034757 0.026364 0.043 Uiso 1 1 calc R U . . . C27 C 0.80179(13) 0.10195(13) 0.08952(6) 0.0283(4) Uani 1 1 d . . . . . H27 H 0.744818 0.092303 0.103379 0.034 Uiso 1 1 calc R U . . . C28 C 0.79428(14) 0.19175(14) 0.06600(7) 0.0353(4) Uani 1 1 d . . . . . H28A H 0.741687 0.190722 0.038197 0.042 Uiso 1 1 calc R U . . . H28B H 0.778412 0.234579 0.088798 0.042 Uiso 1 1 calc R U . . . C29 C 0.88272(16) 0.22287(15) 0.04954(7) 0.0403(5) Uani 1 1 d . . . . . H29A H 0.878231 0.286429 0.044981 0.048 Uiso 1 1 calc R U . . . H29B H 0.883414 0.196511 0.018224 0.048 Uiso 1 1 calc R U . . . C30 C 0.97682(14) 0.20230(15) 0.08300(7) 0.0374(5) Uani 1 1 d . . . . . H30A H 0.989531 0.248189 0.107510 0.045 Uiso 1 1 calc R U . . . H30B H 1.027086 0.205289 0.064382 0.045 Uiso 1 1 calc R U . . . C31 C 0.70478(15) -0.01417(14) 0.39572(7) 0.0367(4) Uani 1 1 d . . . . . C32 C 0.57059(19) 0.17883(16) 0.45068(8) 0.0483(6) Uani 1 1 d . . . . . H32 H 0.580964 0.162763 0.418432 0.058 Uiso 1 1 calc R U . . . B1 B 0.89316(14) 0.09941(13) 0.13196(7) 0.0252(4) 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 Cl1 0.0914(6) 0.0804(5) 0.0873(6) -0.0089(4) 0.0505(5) -0.0159(4) Cl2 0.1324(8) 0.0488(4) 0.0646(5) 0.0063(3) 0.0314(5) 0.0166(4) Cl3 0.0906(6) 0.0985(6) 0.0561(4) -0.0101(4) -0.0069(4) 0.0258(5) S1 0.0372(3) 0.0251(2) 0.0266(2) -0.00155(17) 0.01247(18) -0.00401(18) F1 0.0544(9) 0.0778(11) 0.0411(7) 0.0011(7) -0.0043(6) -0.0008(8) F2 0.0942(12) 0.0368(7) 0.0584(9) 0.0097(6) 0.0229(8) 0.0177(7) F3 0.0599(9) 0.0671(9) 0.0499(8) 0.0183(7) 0.0292(7) -0.0025(7) O1 0.0531(9) 0.0279(7) 0.0348(7) -0.0016(6) 0.0173(6) 0.0013(6) O2 0.0529(10) 0.0383(8) 0.0417(8) -0.0054(7) 0.0003(7) -0.0088(7) O3 0.0532(10) 0.0414(8) 0.0503(9) -0.0009(7) 0.0330(8) -0.0031(7) N1 0.0288(8) 0.0280(8) 0.0195(7) 0.0000(6) 0.0076(6) 0.0000(6) N2 0.0248(7) 0.0275(7) 0.0192(7) 0.0011(6) 0.0046(5) -0.0023(6) C1 0.0397(11) 0.0326(10) 0.0232(9) -0.0043(7) 0.0115(7) 0.0022(8) C2 0.0349(10) 0.0270(9) 0.0292(9) -0.0042(7) 0.0102(7) 0.0021(7) C3 0.0213(8) 0.0277(9) 0.0245(8) -0.0004(7) 0.0047(6) -0.0009(7) C4 0.0265(9) 0.0271(9) 0.0219(8) -0.0022(7) 0.0068(6) -0.0015(7) C5 0.0215(8) 0.0272(9) 0.0202(8) -0.0027(6) 0.0049(6) -0.0009(7) C6 0.0213(8) 0.0261(8) 0.0205(8) 0.0014(6) 0.0055(6) -0.0019(6) C7 0.0257(9) 0.0263(8) 0.0203(8) 0.0001(7) 0.0063(6) -0.0023(7) C8 0.0208(8) 0.0265(9) 0.0241(8) -0.0010(7) 0.0043(6) -0.0023(6) C9 0.0322(10) 0.0239(9) 0.0291(9) 0.0020(7) 0.0057(7) -0.0023(7) C10 0.0331(10) 0.0299(9) 0.0238(9) 0.0058(7) 0.0065(7) -0.0033(7) C11 0.0222(8) 0.0283(9) 0.0284(9) 0.0013(7) 0.0052(7) 0.0004(7) C12 0.0433(11) 0.0296(10) 0.0328(10) -0.0006(8) 0.0081(8) 0.0020(8) C13 0.0574(14) 0.0274(10) 0.0481(13) 0.0057(9) 0.0135(10) 0.0052(10) C14 0.0451(12) 0.0387(11) 0.0472(12) 0.0179(10) 0.0169(10) 0.0090(9) C15 0.0479(13) 0.0436(12) 0.0374(11) 0.0112(9) 0.0212(9) 0.0093(10) C16 0.0409(11) 0.0312(10) 0.0349(10) 0.0049(8) 0.0170(8) 0.0063(8) C17 0.0229(8) 0.0245(8) 0.0258(8) -0.0023(7) 0.0031(6) 0.0016(6) C18 0.0257(9) 0.0295(9) 0.0280(9) -0.0021(7) 0.0045(7) -0.0014(7) C19 0.0320(10) 0.0388(11) 0.0294(9) -0.0034(8) 0.0094(7) 0.0028(8) C20 0.0399(11) 0.0367(11) 0.0334(10) -0.0129(8) 0.0053(8) 0.0060(9) C21 0.0397(11) 0.0257(9) 0.0438(11) -0.0104(8) 0.0071(9) -0.0001(8) C22 0.0341(10) 0.0253(9) 0.0358(10) -0.0020(8) 0.0093(8) -0.0003(7) C23 0.0239(9) 0.0477(11) 0.0228(9) 0.0008(8) 0.0053(7) -0.0034(8) C24 0.0382(11) 0.0515(13) 0.0301(10) 0.0004(9) 0.0177(8) 0.0028(9) C25 0.0524(13) 0.0467(12) 0.0245(9) -0.0056(9) 0.0140(9) -0.0003(10) C26 0.0379(11) 0.0434(11) 0.0240(9) -0.0040(8) 0.0031(8) -0.0061(9) C27 0.0244(9) 0.0386(10) 0.0223(8) -0.0004(7) 0.0057(7) -0.0036(7) C28 0.0355(11) 0.0424(11) 0.0255(9) 0.0030(8) 0.0002(7) 0.0019(9) C29 0.0497(13) 0.0411(11) 0.0295(10) 0.0089(9) 0.0069(9) -0.0051(10) C30 0.0364(11) 0.0489(12) 0.0297(10) 0.0007(9) 0.0132(8) -0.0132(9) C31 0.0410(11) 0.0374(11) 0.0339(10) 0.0028(8) 0.0124(9) 0.0014(9) C32 0.0653(16) 0.0485(13) 0.0345(11) -0.0020(10) 0.0176(10) 0.0056(11) B1 0.0289(10) 0.0283(10) 0.0191(9) 0.0000(7) 0.0066(7) -0.0012(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (Vol. C, Table 6.1.1.4) ; B B 0.0013 0.0007 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.0171 0.0103 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.1246 0.1234 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.1484 0.1585 ; International Tables for Crystallography (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 O2 S1 O3 115.02(10) . . ? O2 S1 O1 115.05(10) . . ? O3 S1 O1 114.90(9) . . ? O2 S1 C31 103.47(10) . . ? O3 S1 C31 102.67(10) . . ? O1 S1 C31 103.29(9) . . ? C1 N1 C5 117.31(15) . . ? C1 N1 B1 129.72(15) . . ? C5 N1 B1 112.86(14) . . ? C10 N2 C6 117.60(15) . . ? C10 N2 B1 129.63(15) . . ? C6 N2 B1 112.77(14) . . ? N1 C1 C2 122.38(16) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 121.10(17) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 116.16(16) . . ? C4 C3 C11 121.84(16) . . ? C2 C3 C11 121.98(16) . . ? C5 C4 C3 119.80(16) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 123.22(16) . . ? N1 C5 C6 109.69(15) . . ? C4 C5 C6 127.07(15) . . ? N2 C6 C7 123.18(16) . . ? N2 C6 C5 109.64(15) . . ? C7 C6 C5 127.14(15) . . ? C6 C7 C8 119.46(16) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C7 C8 C9 116.67(16) . . ? C7 C8 C17 121.40(16) . . ? C9 C8 C17 121.91(16) . . ? C10 C9 C8 121.05(17) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? N2 C10 C9 122.03(16) . . ? N2 C10 H10 119.0 . . ? C9 C10 H10 119.0 . . ? C12 C11 C16 118.18(17) . . ? C12 C11 C3 120.83(17) . . ? C16 C11 C3 120.95(17) . . ? C13 C12 C11 121.04(19) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 120.2(2) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 119.47(19) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C16 C15 C14 120.5(2) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C11 120.59(19) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C18 C17 C22 118.75(16) . . ? C18 C17 C8 120.78(16) . . ? C22 C17 C8 120.43(16) . . ? C19 C18 C17 120.55(18) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 120.15(19) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C21 C20 C19 119.84(18) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 120.13(18) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C17 120.54(18) . . ? C21 C22 H22 119.7 . . ? C17 C22 H22 119.7 . . ? C24 C23 C30 110.78(15) . . ? C24 C23 B1 109.82(16) . . ? C30 C23 B1 109.85(16) . . ? C24 C23 H23 108.8 . . ? C30 C23 H23 108.8 . . ? B1 C23 H23 108.8 . . ? C25 C24 C23 114.69(17) . . ? C25 C24 H24A 108.6 . . ? C23 C24 H24A 108.6 . . ? C25 C24 H24B 108.6 . . ? C23 C24 H24B 108.6 . . ? H24A C24 H24B 107.6 . . ? C24 C25 C26 115.48(16) . . ? C24 C25 H25A 108.4 . . ? C26 C25 H25A 108.4 . . ? C24 C25 H25B 108.4 . . ? C26 C25 H25B 108.4 . . ? H25A C25 H25B 107.5 . . ? C25 C26 C27 115.31(17) . . ? C25 C26 H26A 108.4 . . ? C27 C26 H26A 108.4 . . ? C25 C26 H26B 108.4 . . ? C27 C26 H26B 108.4 . . ? H26A C26 H26B 107.5 . . ? C28 C27 C26 112.42(15) . . ? C28 C27 B1 109.25(15) . . ? C26 C27 B1 109.47(15) . . ? C28 C27 H27 108.5 . . ? C26 C27 H27 108.5 . . ? B1 C27 H27 108.5 . . ? C29 C28 C27 115.34(17) . . ? C29 C28 H28A 108.4 . . ? C27 C28 H28A 108.4 . . ? C29 C28 H28B 108.4 . . ? C27 C28 H28B 108.4 . . ? H28A C28 H28B 107.5 . . ? C28 C29 C30 115.99(16) . . ? C28 C29 H29A 108.3 . . ? C30 C29 H29A 108.3 . . ? C28 C29 H29B 108.3 . . ? C30 C29 H29B 108.3 . . ? H29A C29 H29B 107.4 . . ? C29 C30 C23 116.17(16) . . ? C29 C30 H30A 108.2 . . ? C23 C30 H30A 108.2 . . ? C29 C30 H30B 108.2 . . ? C23 C30 H30B 108.2 . . ? H30A C30 H30B 107.4 . . ? F1 C31 F3 107.19(17) . . ? F1 C31 F2 107.65(18) . . ? F3 C31 F2 107.38(18) . . ? F1 C31 S1 112.02(15) . . ? F3 C31 S1 111.58(15) . . ? F2 C31 S1 110.79(14) . . ? Cl3 C32 Cl1 111.06(14) . . ? Cl3 C32 Cl2 110.00(14) . . ? Cl1 C32 Cl2 110.19(15) . . ? Cl3 C32 H32 108.5 . . ? Cl1 C32 H32 108.5 . . ? Cl2 C32 H32 108.5 . . ? C23 B1 N1 116.24(15) . . ? C23 B1 C27 107.22(14) . . ? N1 B1 C27 111.49(15) . . ? C23 B1 N2 114.57(15) . . ? N1 B1 N2 94.60(12) . . ? C27 B1 N2 112.53(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 Cl1 C32 1.753(3) . ? Cl2 C32 1.754(3) . ? Cl3 C32 1.745(3) . ? S1 O2 1.4345(16) . ? S1 O3 1.4392(15) . ? S1 O1 1.4400(14) . ? S1 C31 1.823(2) . ? F1 C31 1.317(3) . ? F2 C31 1.338(3) . ? F3 C31 1.329(2) . ? N1 C1 1.347(2) . ? N1 C5 1.358(2) . ? N1 B1 1.611(2) . ? N2 C10 1.349(2) . ? N2 C6 1.359(2) . ? N2 B1 1.615(2) . ? C1 C2 1.372(3) . ? C1 H1 0.9500 . ? C2 C3 1.405(2) . ? C2 H2 0.9500 . ? C3 C4 1.399(2) . ? C3 C11 1.482(2) . ? C4 C5 1.379(2) . ? C4 H4 0.9500 . ? C5 C6 1.456(2) . ? C6 C7 1.381(2) . ? C7 C8 1.398(2) . ? C7 H7 0.9500 . ? C8 C9 1.403(2) . ? C8 C17 1.478(2) . ? C9 C10 1.374(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.394(3) . ? C11 C16 1.398(3) . ? C12 C13 1.381(3) . ? C12 H12 0.9500 . ? C13 C14 1.384(3) . ? C13 H13 0.9500 . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 C16 1.382(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.396(3) . ? C17 C22 1.398(3) . ? C18 C19 1.385(3) . ? C18 H18 0.9500 . ? C19 C20 1.389(3) . ? C19 H19 0.9500 . ? C20 C21 1.386(3) . ? C20 H20 0.9500 . ? C21 C22 1.386(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.543(3) . ? C23 C30 1.546(3) . ? C23 B1 1.610(3) . ? C23 H23 1.0000 . ? C24 C25 1.536(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.538(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.545(3) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.536(3) . ? C27 B1 1.615(3) . ? C27 H27 1.0000 . ? C28 C29 1.534(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.541(3) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C32 H32 1.0000 . ? 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 C5 N1 C1 C2 -0.5(3) . . . . ? B1 N1 C1 C2 -176.43(18) . . . . ? N1 C1 C2 C3 1.2(3) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C1 C2 C3 C11 -178.58(17) . . . . ? C2 C3 C4 C5 -1.1(3) . . . . ? C11 C3 C4 C5 177.15(16) . . . . ? C1 N1 C5 C4 -1.0(3) . . . . ? B1 N1 C5 C4 175.58(16) . . . . ? C1 N1 C5 C6 177.48(16) . . . . ? B1 N1 C5 C6 -5.9(2) . . . . ? C3 C4 C5 N1 1.9(3) . . . . ? C3 C4 C5 C6 -176.36(16) . . . . ? C10 N2 C6 C7 -0.5(3) . . . . ? B1 N2 C6 C7 -179.68(16) . . . . ? C10 N2 C6 C5 -178.25(15) . . . . ? B1 N2 C6 C5 2.6(2) . . . . ? N1 C5 C6 N2 2.1(2) . . . . ? C4 C5 C6 N2 -179.47(17) . . . . ? N1 C5 C6 C7 -175.56(17) . . . . ? C4 C5 C6 C7 2.9(3) . . . . ? N2 C6 C7 C8 -0.6(3) . . . . ? C5 C6 C7 C8 176.77(16) . . . . ? C6 C7 C8 C9 1.4(3) . . . . ? C6 C7 C8 C17 -177.32(16) . . . . ? C7 C8 C9 C10 -1.2(3) . . . . ? C17 C8 C9 C10 177.51(17) . . . . ? C6 N2 C10 C9 0.7(3) . . . . ? B1 N2 C10 C9 179.74(17) . . . . ? C8 C9 C10 N2 0.1(3) . . . . ? C4 C3 C11 C12 -178.78(17) . . . . ? C2 C3 C11 C12 -0.6(3) . . . . ? C4 C3 C11 C16 -0.8(3) . . . . ? C2 C3 C11 C16 177.36(18) . . . . ? C16 C11 C12 C13 -1.1(3) . . . . ? C3 C11 C12 C13 176.96(19) . . . . ? C11 C12 C13 C14 0.1(3) . . . . ? C12 C13 C14 C15 0.5(4) . . . . ? C13 C14 C15 C16 -0.2(4) . . . . ? C14 C15 C16 C11 -0.7(3) . . . . ? C12 C11 C16 C15 1.3(3) . . . . ? C3 C11 C16 C15 -176.66(19) . . . . ? C7 C8 C17 C18 -26.1(3) . . . . ? C9 C8 C17 C18 155.25(17) . . . . ? C7 C8 C17 C22 151.79(18) . . . . ? C9 C8 C17 C22 -26.8(3) . . . . ? C22 C17 C18 C19 0.0(3) . . . . ? C8 C17 C18 C19 177.94(17) . . . . ? C17 C18 C19 C20 -1.3(3) . . . . ? C18 C19 C20 C21 1.1(3) . . . . ? C19 C20 C21 C22 0.5(3) . . . . ? C20 C21 C22 C17 -1.8(3) . . . . ? C18 C17 C22 C21 1.6(3) . . . . ? C8 C17 C22 C21 -176.39(18) . . . . ? C30 C23 C24 C25 -68.7(2) . . . . ? B1 C23 C24 C25 52.9(2) . . . . ? C23 C24 C25 C26 -42.3(3) . . . . ? C24 C25 C26 C27 42.0(3) . . . . ? C25 C26 C27 C28 69.9(2) . . . . ? C25 C26 C27 B1 -51.7(2) . . . . ? C26 C27 C28 C29 -68.8(2) . . . . ? B1 C27 C28 C29 52.9(2) . . . . ? C27 C28 C29 C30 -39.8(3) . . . . ? C28 C29 C30 C23 37.6(3) . . . . ? C24 C23 C30 C29 72.8(2) . . . . ? B1 C23 C30 C29 -48.7(2) . . . . ? O2 S1 C31 F1 -179.80(15) . . . . ? O3 S1 C31 F1 60.22(17) . . . . ? O1 S1 C31 F1 -59.55(17) . . . . ? O2 S1 C31 F3 -59.62(17) . . . . ? O3 S1 C31 F3 -179.59(15) . . . . ? O1 S1 C31 F3 60.64(17) . . . . ? O2 S1 C31 F2 59.97(18) . . . . ? O3 S1 C31 F2 -60.00(17) . . . . ? O1 S1 C31 F2 -179.77(15) . . . . ? C24 C23 B1 N1 63.9(2) . . . . ? C30 C23 B1 N1 -174.05(15) . . . . ? C24 C23 B1 C27 -61.6(2) . . . . ? C30 C23 B1 C27 60.48(19) . . . . ? C24 C23 B1 N2 172.76(15) . . . . ? C30 C23 B1 N2 -65.16(19) . . . . ? C1 N1 B1 C23 -57.1(2) . . . . ? C5 N1 B1 C23 126.86(16) . . . . ? C1 N1 B1 C27 66.2(2) . . . . ? C5 N1 B1 C27 -109.86(17) . . . . ? C1 N1 B1 N2 -177.38(18) . . . . ? C5 N1 B1 N2 6.55(17) . . . . ? C28 C27 B1 C23 -62.73(19) . . . . ? C26 C27 B1 C23 60.77(19) . . . . ? C28 C27 B1 N1 168.99(15) . . . . ? C26 C27 B1 N1 -67.51(19) . . . . ? C28 C27 B1 N2 64.12(19) . . . . ? C26 C27 B1 N2 -172.38(15) . . . . ? C10 N2 B1 C23 54.1(2) . . . . ? C6 N2 B1 C23 -126.86(16) . . . . ? C10 N2 B1 N1 175.71(17) . . . . ? C6 N2 B1 N1 -5.23(17) . . . . ? C10 N2 B1 C27 -68.7(2) . . . . ? C6 N2 B1 C27 110.32(17) . . . . ?