#------------------------------------------------------------------------------ #$Date: 2026-06-12 23:11:39 +0100 (Fri, 12 Jun 2026) $ #$Revision: 306559 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577398.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_1577398 loop_ _publ_author_name 'Li, Hai-Jun' 'Xi, Biying' 'Jing, Hui-Xian' 'Li, Xin' 'Jia, Hongnan' 'Fan, Manman' 'Zhu, Weiguo' 'Feng, Rui' 'Hao, Baorui' 'Li, Shi-Jun' 'Yu, Bing' 'Lan, Yu' 'Du, Jingzhen' _publ_section_title ; Photo-Induced Terminal Alkyne Insertion into Arene Ring to Synthesize Boron-Doped Polycycles ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC02310J _journal_year 2026 _chemical_formula_moiety 'C25 H27 B S' _chemical_formula_sum 'C25 H27 B S' _chemical_formula_weight 370.33 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2025-06-05 _audit_creation_method ; Olex2 1.5 (compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188) ; _audit_update_record ; 2025-06-05 deposited with the CCDC. 2026-06-11 downloaded from the CCDC. ; _cell_angle_alpha 87.512(5) _cell_angle_beta 82.495(5) _cell_angle_gamma 74.927(5) _cell_formula_units_Z 2 _cell_length_a 8.2159(4) _cell_length_b 11.6107(7) _cell_length_c 12.0340(8) _cell_measurement_reflns_used 3786 _cell_measurement_temperature 293.00(10) _cell_measurement_theta_max 70.7490 _cell_measurement_theta_min 3.9480 _cell_volume 1098.91(12) _computing_cell_refinement 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)' _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 293.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.2312 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.974 _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 -52.00 35.00 1.00 1.00 -- -33.50 57.00 -30.00 87 2 \w -102.00 -15.00 1.00 1.00 -- -33.50 -57.00 90.00 87 3 \w -71.00 39.00 1.00 1.00 -- -33.50 19.00 -90.00 110 4 \w 14.00 107.00 1.00 1.00 -- 36.47 37.00 90.00 93 5 \w 61.00 110.00 1.00 1.00 -- 36.47 178.00 120.00 49 6 \w 1.00 76.00 1.00 1.00 -- 36.47 -99.00 120.00 75 7 \w -18.00 65.00 1.00 1.00 -- 36.47 -77.00-150.00 83 8 \w -18.00 65.00 1.00 1.00 -- 36.47 -77.00 -30.00 83 9 \w 56.00 92.00 1.00 1.00 -- 36.47-132.00 -73.00 36 10 \w 66.00 109.00 1.00 1.00 -- 36.47 19.00 30.00 43 11 \w 44.00 71.00 1.00 1.00 -- 36.47 -99.00-180.00 27 12 \w 9.00 61.00 1.00 1.00 -- 36.47 19.00 30.00 52 13 \w 61.00 86.00 1.00 1.00 -- 36.47 178.00 150.00 25 14 \w 71.00 101.00 1.00 3.50 -- 108.00 -94.00-150.00 30 15 \w 48.00 109.00 1.00 3.50 -- 108.00-111.00 -30.00 61 16 \w 101.00 132.00 1.00 3.50 -- 108.00 61.00 -30.00 31 17 \w 48.00 127.00 1.00 3.50 -- 108.00 -61.00 -30.00 79 18 \w 38.00 63.00 1.00 3.50 -- 108.00 -94.00 0.00 25 19 \w 42.00 131.00 1.00 3.50 -- 108.00 -30.00 120.00 89 20 \w 78.00 126.00 1.00 3.50 -- 108.00 -61.00 30.00 48 21 \w 150.00 176.00 1.00 3.50 -- 108.00 45.00 120.00 26 22 \w 75.00 108.00 1.00 3.50 -- 108.00-111.00 150.00 33 23 \w 45.00 133.00 1.00 3.50 -- 108.00 -30.00-150.00 88 24 \w 91.00 133.00 1.00 3.50 -- 108.00 45.00 120.00 42 25 \w 53.00 79.00 1.00 3.50 -- 108.00 -94.00-180.00 26 26 \w 69.00 104.00 1.00 3.50 -- 108.00 -94.00 30.00 35 27 \w 36.00 149.00 1.00 3.50 -- 108.00 -15.00 -60.00 113 28 \w 115.00 171.00 1.00 3.50 -- 108.00 77.00 -60.00 56 29 \w 44.00 103.00 1.00 3.50 -- 108.00 -61.00-180.00 59 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0088238000 _diffrn_orient_matrix_UB_12 -0.0885261000 _diffrn_orient_matrix_UB_13 0.0995298000 _diffrn_orient_matrix_UB_21 0.0418936000 _diffrn_orient_matrix_UB_22 -0.1047104000 _diffrn_orient_matrix_UB_23 -0.0822182000 _diffrn_orient_matrix_UB_31 0.1909541000 _diffrn_orient_matrix_UB_32 -0.0091058000 _diffrn_orient_matrix_UB_33 -0.0029291000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_unetI/netI 0.0374 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.974 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 7936 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.974 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 70.868 _diffrn_reflns_theta_min 3.705 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.324 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.82972 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.119 _exptl_crystal_description block _exptl_crystal_F_000 396 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.228 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 251 _refine_ls_number_reflns 4125 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0662 _refine_ls_R_factor_gt 0.0562 _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^)+(0.0991P)^2^+0.1002P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1606 _refine_ls_wR_factor_ref 0.1754 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3346 _reflns_number_total 4125 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc02310j2.cif _cod_data_source_block 202406213_auto _cod_database_code 1577398 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula C20H2N1O4B1S1 _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 0.879 _shelx_estimated_absorpt_t_min 0.816 _reflns_odcompleteness_completeness 99.97 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C21(H21), C19(H19), C10(H10), C3(H3), C12(H12) 2.b Idealised Me refined as rotating group: C14(H14A,H14B,H14C), C25(H25A,H25B,H25C), C23(H23A,H23B,H23C), C16(H16A,H16B, H16C), C24(H24A,H24B,H24C), C15(H15A,H15B,H15C), C7(H7A,H7B,H7C) 2.c : C6(H6) ; _shelx_res_file ; TITL 202406213_auto_a.res in P-1 202406213_auto.res created by SHELXL-2019/3 at 14:42:45 on 05-Jun-2025 REM Old TITL REM SHELXT solution in P-1: R1 0.186, Rweak 0.014, Alpha 0.037 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C25 S O CELL 1.54184 8.2159 11.6107 12.034 87.512 82.495 74.927 ZERR 2 0.0004 0.0007 0.0008 0.005 0.005 0.005 LATT 1 SFAC C H B S UNIT 50 54 2 2 L.S. 4 PLAN 10 SIZE 0.1 0.11 0.16 TEMP 19.85(10) CONF BOND list 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.099100 0.100200 FVAR 1.13172 S1 4 0.924020 0.055703 0.694989 11.00000 0.06355 0.04560 = 0.08523 -0.00746 -0.00878 -0.01434 C17 1 0.604831 0.257866 0.651729 11.00000 0.04522 0.04558 = 0.05269 -0.00058 -0.00609 -0.01251 C1 1 0.873538 0.191288 0.762787 11.00000 0.04866 0.04603 = 0.06083 -0.00024 -0.00805 -0.01546 C18 1 0.505178 0.180572 0.697608 11.00000 0.04926 0.05102 = 0.05796 0.00078 -0.00544 -0.01525 C9 1 0.858277 0.478797 0.727700 11.00000 0.05797 0.04738 = 0.05861 0.00092 -0.01648 -0.01383 C22 1 0.589259 0.298409 0.540635 11.00000 0.05109 0.05125 = 0.05348 -0.00279 -0.00489 -0.01376 C2 1 0.968087 0.179248 0.851734 11.00000 0.04513 0.05766 = 0.06169 0.00592 -0.00646 -0.01470 C8 1 0.719566 0.427751 0.753411 11.00000 0.05106 0.04565 = 0.04913 -0.00064 -0.01298 -0.01009 C13 1 0.568071 0.497886 0.811468 11.00000 0.05404 0.05416 = 0.05720 -0.00373 -0.01317 -0.00452 C21 1 0.478860 0.262738 0.479074 11.00000 0.05949 0.06749 = 0.05111 -0.00386 -0.00960 -0.01558 AFIX 43 H21 2 0.469678 0.290914 0.406030 11.00000 -1.20000 AFIX 0 C19 1 0.397081 0.146836 0.633594 11.00000 0.05227 0.05621 = 0.07229 -0.00376 -0.00413 -0.02283 AFIX 43 H19 2 0.332311 0.096108 0.665121 11.00000 -1.20000 AFIX 0 C20 1 0.382438 0.186346 0.523972 11.00000 0.05213 0.06471 = 0.06218 -0.01377 -0.00852 -0.01587 C10 1 0.842627 0.595243 0.761189 11.00000 0.07474 0.05116 = 0.06830 0.00120 -0.02139 -0.02289 AFIX 43 H10 2 0.934048 0.628666 0.742626 11.00000 -1.20000 AFIX 0 C3 1 1.074506 0.062796 0.863159 11.00000 0.04857 0.06814 = 0.08040 0.02063 -0.01132 -0.01331 AFIX 43 H3 2 1.143149 0.040837 0.920173 11.00000 -1.20000 AFIX 0 C11 1 0.696690 0.662339 0.820704 11.00000 0.08949 0.04704 = 0.06314 -0.00452 -0.02898 -0.00971 C12 1 0.561949 0.612008 0.845498 11.00000 0.06900 0.05661 = 0.06189 -0.01048 -0.01724 0.00418 AFIX 43 H12 2 0.463113 0.655914 0.886530 11.00000 -1.20000 AFIX 0 C14 1 1.022688 0.413393 0.662173 11.00000 0.05661 0.06339 = 0.08558 -0.00297 -0.00074 -0.02395 AFIX 137 H14A 2 1.100357 0.373269 0.713040 11.00000 -1.50000 H14B 2 1.071078 0.469263 0.616985 11.00000 -1.50000 H14C 2 1.001541 0.355912 0.614681 11.00000 -1.50000 AFIX 0 C4 1 1.066597 -0.013436 0.783030 11.00000 0.05120 0.04989 = 0.10441 0.01124 -0.00277 -0.00888 C5 1 0.962448 0.273125 0.926735 11.00000 0.06499 0.07859 = 0.06252 0.00159 -0.01905 -0.01301 C25 1 0.694711 0.378427 0.484287 11.00000 0.07615 0.07696 = 0.05846 0.01025 -0.00554 -0.03361 AFIX 137 H25A 2 0.683178 0.445549 0.531251 11.00000 -1.50000 H25B 2 0.656105 0.406026 0.413564 11.00000 -1.50000 H25C 2 0.811833 0.334533 0.472253 11.00000 -1.50000 AFIX 0 C23 1 0.502807 0.137481 0.818300 11.00000 0.07558 0.07632 = 0.06927 0.01871 -0.01178 -0.03677 AFIX 137 H23A 2 0.579461 0.168787 0.854391 11.00000 -1.50000 H23B 2 0.537537 0.051900 0.820266 11.00000 -1.50000 H23C 2 0.389920 0.164449 0.856730 11.00000 -1.50000 AFIX 0 B1 3 0.732033 0.294988 0.722191 11.00000 0.04650 0.04589 = 0.04923 -0.00023 -0.00269 -0.01361 C16 1 0.412185 0.452631 0.842676 11.00000 0.05738 0.08605 = 0.09302 -0.01871 0.00725 -0.01125 AFIX 137 H16A 2 0.373795 0.432288 0.775941 11.00000 -1.50000 H16B 2 0.324206 0.513535 0.882129 11.00000 -1.50000 H16C 2 0.439109 0.383200 0.889865 11.00000 -1.50000 AFIX 0 C24 1 0.264743 0.146687 0.456679 11.00000 0.07806 0.10455 = 0.08187 -0.01489 -0.02078 -0.04033 AFIX 137 H24A 2 0.211493 0.211881 0.410956 11.00000 -1.50000 H24B 2 0.179264 0.121432 0.506592 11.00000 -1.50000 H24C 2 0.328501 0.081488 0.409625 11.00000 -1.50000 AFIX 0 C15 1 0.683238 0.787479 0.858435 11.00000 0.12855 0.05482 = 0.10089 -0.01958 -0.03081 -0.01371 AFIX 137 H15A 2 0.696459 0.786038 0.936616 11.00000 -1.50000 H15B 2 0.574016 0.838061 0.846757 11.00000 -1.50000 H15C 2 0.770707 0.817722 0.815869 11.00000 -1.50000 AFIX 0 C6 1 0.968196 0.344709 0.990912 11.00000 0.10492 0.09671 = 0.07899 -0.01675 -0.02827 -0.01884 AFIX 163 H6 2 0.972754 0.401479 1.041808 11.00000 -1.20000 AFIX 0 C7 1 1.167981 -0.140660 0.764636 11.00000 0.08642 0.05684 = 0.16634 0.00592 -0.00144 0.00406 AFIX 137 H7A 2 1.095075 -0.187724 0.746263 11.00000 -1.50000 H7B 2 1.215949 -0.171770 0.831736 11.00000 -1.50000 H7C 2 1.257589 -0.143637 0.704175 11.00000 -1.50000 AFIX 0 HKLF 4 REM 202406213_auto_a.res in P-1 REM wR2 = 0.1754, GooF = S = 1.053, Restrained GooF = 1.053 for all data REM R1 = 0.0562 for 3346 Fo > 4sig(Fo) and 0.0662 for all 4125 data REM 251 parameters refined using 0 restraints END WGHT 0.0991 0.1002 REM Highest difference peak 0.228, deepest hole -0.224, 1-sigma level 0.045 Q1 1 0.8108 0.2402 0.7439 11.00000 0.05 0.23 Q2 1 0.5640 0.8091 0.9336 11.00000 0.05 0.22 Q3 1 0.2784 0.0603 0.4786 11.00000 0.05 0.20 Q4 1 1.0528 0.3232 0.6686 11.00000 0.05 0.20 Q5 1 0.6146 0.1050 0.8445 11.00000 0.05 0.20 Q6 1 0.7219 0.3662 0.7380 11.00000 0.05 0.19 Q7 1 0.4214 0.0909 0.8415 11.00000 0.05 0.18 Q8 1 0.6588 0.8468 0.7832 11.00000 0.05 0.18 Q9 1 0.9141 0.1435 0.7003 11.00000 0.05 0.17 Q10 1 0.6695 0.2761 0.6842 11.00000 0.05 0.16 ; _shelx_res_checksum 56729 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.241 _oxdiff_exptl_absorpt_empirical_full_min 0.859 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 S1 S 0.92402(8) 0.05570(5) 0.69499(6) 0.0646(2) Uani 1 1 d . . . . . C17 C 0.6048(2) 0.25787(17) 0.65173(16) 0.0477(4) Uani 1 1 d . . . . . C1 C 0.8735(3) 0.19129(18) 0.76279(18) 0.0511(5) Uani 1 1 d . . . . . C18 C 0.5052(3) 0.18057(19) 0.69761(18) 0.0525(5) Uani 1 1 d . . . . . C9 C 0.8583(3) 0.47880(19) 0.72770(18) 0.0538(5) Uani 1 1 d . . . . . C22 C 0.5893(3) 0.29841(18) 0.54063(17) 0.0519(5) Uani 1 1 d . . . . . C2 C 0.9681(3) 0.1792(2) 0.85173(18) 0.0548(5) Uani 1 1 d . . . . . C8 C 0.7196(3) 0.42775(17) 0.75341(16) 0.0484(4) Uani 1 1 d . . . . . C13 C 0.5681(3) 0.4979(2) 0.81147(18) 0.0562(5) Uani 1 1 d . . . . . C21 C 0.4789(3) 0.2627(2) 0.47907(18) 0.0591(5) Uani 1 1 d . . . . . H21 H 0.469678 0.290914 0.406030 0.071 Uiso 1 1 calc R U . . . C19 C 0.3971(3) 0.1468(2) 0.6336(2) 0.0588(5) Uani 1 1 d . . . . . H19 H 0.332311 0.096108 0.665121 0.071 Uiso 1 1 calc R U . . . C20 C 0.3824(3) 0.1863(2) 0.52397(19) 0.0590(5) Uani 1 1 d . . . . . C10 C 0.8426(3) 0.5952(2) 0.7612(2) 0.0624(6) Uani 1 1 d . . . . . H10 H 0.934048 0.628666 0.742626 0.075 Uiso 1 1 calc R U . . . C3 C 1.0745(3) 0.0628(2) 0.8632(2) 0.0664(6) Uani 1 1 d . . . . . H3 H 1.143149 0.040837 0.920173 0.080 Uiso 1 1 calc R U . . . C11 C 0.6967(4) 0.6623(2) 0.8207(2) 0.0661(6) Uani 1 1 d . . . . . C12 C 0.5619(3) 0.6120(2) 0.8455(2) 0.0652(6) Uani 1 1 d . . . . . H12 H 0.463113 0.655914 0.886530 0.078 Uiso 1 1 calc R U . . . C14 C 1.0227(3) 0.4134(2) 0.6622(2) 0.0676(6) Uani 1 1 d . . . . . H14A H 1.100357 0.373269 0.713040 0.101 Uiso 1 1 calc R U . . . H14B H 1.071078 0.469263 0.616985 0.101 Uiso 1 1 calc R U . . . H14C H 1.001541 0.355912 0.614681 0.101 Uiso 1 1 calc R U . . . C4 C 1.0666(3) -0.0134(2) 0.7830(3) 0.0703(7) Uani 1 1 d . . . . . C5 C 0.9624(3) 0.2731(2) 0.9267(2) 0.0688(6) Uani 1 1 d . . . . . C25 C 0.6947(3) 0.3784(2) 0.4843(2) 0.0685(6) Uani 1 1 d . . . . . H25A H 0.683178 0.445549 0.531251 0.103 Uiso 1 1 calc R U . . . H25B H 0.656105 0.406026 0.413564 0.103 Uiso 1 1 calc R U . . . H25C H 0.811833 0.334533 0.472253 0.103 Uiso 1 1 calc R U . . . C23 C 0.5028(4) 0.1375(2) 0.8183(2) 0.0708(7) Uani 1 1 d . . . . . H23A H 0.579461 0.168787 0.854391 0.106 Uiso 1 1 calc R U . . . H23B H 0.537537 0.051900 0.820266 0.106 Uiso 1 1 calc R U . . . H23C H 0.389920 0.164449 0.856730 0.106 Uiso 1 1 calc R U . . . B1 B 0.7320(3) 0.2950(2) 0.72219(19) 0.0472(5) Uani 1 1 d . . . . . C16 C 0.4122(3) 0.4526(3) 0.8427(3) 0.0811(8) Uani 1 1 d . . . . . H16A H 0.373795 0.432288 0.775941 0.122 Uiso 1 1 calc R U . . . H16B H 0.324206 0.513535 0.882129 0.122 Uiso 1 1 calc R U . . . H16C H 0.439109 0.383200 0.889865 0.122 Uiso 1 1 calc R U . . . C24 C 0.2647(4) 0.1467(3) 0.4567(3) 0.0836(8) Uani 1 1 d . . . . . H24A H 0.211493 0.211881 0.410956 0.125 Uiso 1 1 calc R U . . . H24B H 0.179264 0.121432 0.506592 0.125 Uiso 1 1 calc R U . . . H24C H 0.328501 0.081488 0.409625 0.125 Uiso 1 1 calc R U . . . C15 C 0.6832(5) 0.7875(2) 0.8584(3) 0.0945(10) Uani 1 1 d . . . . . H15A H 0.696459 0.786038 0.936616 0.142 Uiso 1 1 calc R U . . . H15B H 0.574016 0.838061 0.846757 0.142 Uiso 1 1 calc R U . . . H15C H 0.770707 0.817722 0.815869 0.142 Uiso 1 1 calc R U . . . C6 C 0.9682(4) 0.3447(3) 0.9909(3) 0.0928(9) Uani 1 1 d . . . . . H6 H 0.972754 0.401479 1.041808 0.111 Uiso 1 1 calc R U . . . C7 C 1.1680(5) -0.1407(3) 0.7646(4) 0.1089(12) Uani 1 1 d . . . . . H7A H 1.095075 -0.187724 0.746263 0.163 Uiso 1 1 calc R U . . . H7B H 1.215949 -0.171770 0.831736 0.163 Uiso 1 1 calc R U . . . H7C H 1.257589 -0.143637 0.704175 0.163 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 S1 0.0635(4) 0.0456(3) 0.0852(4) -0.0075(3) -0.0088(3) -0.0143(2) C17 0.0452(10) 0.0456(10) 0.0527(10) -0.0006(8) -0.0061(8) -0.0125(8) C1 0.0487(11) 0.0460(10) 0.0608(11) -0.0002(8) -0.0081(9) -0.0155(8) C18 0.0493(11) 0.0510(11) 0.0580(11) 0.0008(9) -0.0054(9) -0.0152(8) C9 0.0580(12) 0.0474(11) 0.0586(11) 0.0009(8) -0.0165(9) -0.0138(9) C22 0.0511(11) 0.0512(11) 0.0535(11) -0.0028(8) -0.0049(8) -0.0138(9) C2 0.0451(10) 0.0577(12) 0.0617(12) 0.0059(9) -0.0065(9) -0.0147(9) C8 0.0511(11) 0.0457(10) 0.0491(10) -0.0006(8) -0.0130(8) -0.0101(8) C13 0.0540(12) 0.0542(12) 0.0572(11) -0.0037(9) -0.0132(9) -0.0045(9) C21 0.0595(12) 0.0675(13) 0.0511(11) -0.0039(9) -0.0096(9) -0.0156(10) C19 0.0523(12) 0.0562(12) 0.0723(13) -0.0038(10) -0.0041(10) -0.0228(9) C20 0.0521(12) 0.0647(13) 0.0622(12) -0.0138(10) -0.0085(9) -0.0159(10) C10 0.0747(15) 0.0512(12) 0.0683(13) 0.0012(10) -0.0214(11) -0.0229(11) C3 0.0486(12) 0.0681(15) 0.0804(15) 0.0206(12) -0.0113(10) -0.0133(10) C11 0.0895(17) 0.0470(12) 0.0631(13) -0.0045(9) -0.0290(12) -0.0097(11) C12 0.0690(14) 0.0566(13) 0.0619(13) -0.0105(10) -0.0172(11) 0.0042(11) C14 0.0566(13) 0.0634(14) 0.0856(16) -0.0030(12) -0.0007(11) -0.0239(11) C4 0.0512(12) 0.0499(12) 0.1044(19) 0.0112(12) -0.0028(12) -0.0089(10) C5 0.0650(14) 0.0786(16) 0.0625(13) 0.0016(12) -0.0191(11) -0.0130(12) C25 0.0761(15) 0.0770(16) 0.0585(13) 0.0103(11) -0.0055(11) -0.0336(13) C23 0.0756(16) 0.0763(16) 0.0693(14) 0.0187(12) -0.0118(12) -0.0368(13) B1 0.0465(11) 0.0459(11) 0.0492(11) -0.0002(9) -0.0027(9) -0.0136(9) C16 0.0574(14) 0.0861(19) 0.0930(19) -0.0187(15) 0.0072(13) -0.0112(13) C24 0.0781(18) 0.105(2) 0.0819(17) -0.0149(16) -0.0208(14) -0.0403(16) C15 0.129(3) 0.0548(15) 0.101(2) -0.0196(14) -0.031(2) -0.0137(16) C6 0.105(2) 0.097(2) 0.0790(18) -0.0168(16) -0.0283(17) -0.0188(18) C7 0.086(2) 0.0568(16) 0.166(4) 0.0059(19) -0.001(2) 0.0041(15) 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' B B 0.0090 0.0039 '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 C4 S1 C1 94.04(12) . . ? C18 C17 B1 120.91(18) . . ? C22 C17 C18 117.79(18) . . ? C22 C17 B1 121.28(17) . . ? C2 C1 S1 108.41(16) . . ? C2 C1 B1 132.9(2) . . ? B1 C1 S1 118.56(15) . . ? C17 C18 C23 122.53(19) . . ? C19 C18 C17 120.08(19) . . ? C19 C18 C23 117.28(19) . . ? C8 C9 C14 122.32(19) . . ? C10 C9 C8 119.4(2) . . ? C10 C9 C14 118.2(2) . . ? C17 C22 C25 121.13(19) . . ? C21 C22 C17 120.43(19) . . ? C21 C22 C25 118.42(19) . . ? C1 C2 C3 113.5(2) . . ? C1 C2 C5 124.7(2) . . ? C3 C2 C5 121.8(2) . . ? C9 C8 C13 118.19(19) . . ? C9 C8 B1 121.77(18) . . ? C13 C8 B1 120.02(18) . . ? C8 C13 C16 122.6(2) . . ? C12 C13 C8 119.7(2) . . ? C12 C13 C16 117.7(2) . . ? C22 C21 H21 119.2 . . ? C20 C21 C22 121.6(2) . . ? C20 C21 H21 119.2 . . ? C18 C19 H19 119.0 . . ? C18 C19 C20 122.1(2) . . ? C20 C19 H19 119.0 . . ? C21 C20 C19 117.98(19) . . ? C21 C20 C24 121.5(2) . . ? C19 C20 C24 120.5(2) . . ? C9 C10 H10 118.8 . . ? C11 C10 C9 122.4(2) . . ? C11 C10 H10 118.8 . . ? C2 C3 H3 123.2 . . ? C4 C3 C2 113.6(2) . . ? C4 C3 H3 123.2 . . ? C10 C11 C15 121.6(3) . . ? C12 C11 C10 117.9(2) . . ? C12 C11 C15 120.5(3) . . ? C13 C12 H12 118.8 . . ? C11 C12 C13 122.4(2) . . ? C11 C12 H12 118.8 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C3 C4 S1 110.46(18) . . ? C3 C4 C7 128.4(3) . . ? C7 C4 S1 121.1(3) . . ? C6 C5 C2 175.1(3) . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C1 B1 C17 115.97(17) . . ? C1 B1 C8 120.17(17) . . ? C8 B1 C17 123.85(17) . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C20 C24 H24A 109.5 . . ? C20 C24 H24B 109.5 . . ? C20 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C5 C6 H6 180.0 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 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 S1 C1 1.732(2) . ? S1 C4 1.703(3) . ? C17 C18 1.415(3) . ? C17 C22 1.409(3) . ? C17 B1 1.579(3) . ? C1 C2 1.384(3) . ? C1 B1 1.552(3) . ? C18 C19 1.386(3) . ? C18 C23 1.515(3) . ? C9 C8 1.410(3) . ? C9 C10 1.397(3) . ? C9 C14 1.504(3) . ? C22 C21 1.393(3) . ? C22 C25 1.511(3) . ? C2 C3 1.418(3) . ? C2 C5 1.433(3) . ? C8 C13 1.413(3) . ? C8 B1 1.577(3) . ? C13 C12 1.390(3) . ? C13 C16 1.505(4) . ? C21 H21 0.9300 . ? C21 C20 1.385(3) . ? C19 H19 0.9300 . ? C19 C20 1.388(3) . ? C20 C24 1.507(3) . ? C10 H10 0.9300 . ? C10 C11 1.377(4) . ? C3 H3 0.9300 . ? C3 C4 1.356(4) . ? C11 C12 1.375(4) . ? C11 C15 1.513(3) . ? C12 H12 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C4 C7 1.505(4) . ? C5 C6 1.173(4) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C6 H6 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? 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 S1 C1 C2 C3 -0.8(2) . . . . ? S1 C1 C2 C5 179.18(19) . . . . ? S1 C1 B1 C17 20.0(2) . . . . ? S1 C1 B1 C8 -160.99(15) . . . . ? C17 C18 C19 C20 0.1(3) . . . . ? C17 C22 C21 C20 -0.5(3) . . . . ? C1 S1 C4 C3 1.0(2) . . . . ? C1 S1 C4 C7 -177.0(2) . . . . ? C1 C2 C3 C4 1.7(3) . . . . ? C18 C17 C22 C21 0.0(3) . . . . ? C18 C17 C22 C25 -178.3(2) . . . . ? C18 C17 B1 C1 59.4(3) . . . . ? C18 C17 B1 C8 -119.5(2) . . . . ? C18 C19 C20 C21 -0.6(3) . . . . ? C18 C19 C20 C24 179.4(2) . . . . ? C9 C8 C13 C12 -2.7(3) . . . . ? C9 C8 C13 C16 179.7(2) . . . . ? C9 C8 B1 C17 -125.8(2) . . . . ? C9 C8 B1 C1 55.3(3) . . . . ? C9 C10 C11 C12 -1.2(3) . . . . ? C9 C10 C11 C15 178.7(2) . . . . ? C22 C17 C18 C19 0.2(3) . . . . ? C22 C17 C18 C23 -176.1(2) . . . . ? C22 C17 B1 C1 -119.2(2) . . . . ? C22 C17 B1 C8 61.8(3) . . . . ? C22 C21 C20 C19 0.8(3) . . . . ? C22 C21 C20 C24 -179.2(2) . . . . ? C2 C1 B1 C17 -154.8(2) . . . . ? C2 C1 B1 C8 24.2(3) . . . . ? C2 C3 C4 S1 -1.7(3) . . . . ? C2 C3 C4 C7 176.1(3) . . . . ? C8 C9 C10 C11 1.2(3) . . . . ? C8 C13 C12 C11 2.8(3) . . . . ? C13 C8 B1 C17 56.0(3) . . . . ? C13 C8 B1 C1 -122.9(2) . . . . ? C10 C9 C8 C13 0.8(3) . . . . ? C10 C9 C8 B1 -177.46(18) . . . . ? C10 C11 C12 C13 -0.9(3) . . . . ? C14 C9 C8 C13 -177.5(2) . . . . ? C14 C9 C8 B1 4.3(3) . . . . ? C14 C9 C10 C11 179.5(2) . . . . ? C4 S1 C1 C2 -0.12(17) . . . . ? C4 S1 C1 B1 -176.13(17) . . . . ? C5 C2 C3 C4 -178.3(2) . . . . ? C25 C22 C21 C20 177.8(2) . . . . ? C23 C18 C19 C20 176.6(2) . . . . ? B1 C17 C18 C19 -178.53(19) . . . . ? B1 C17 C18 C23 5.2(3) . . . . ? B1 C17 C22 C21 178.69(19) . . . . ? B1 C17 C22 C25 0.4(3) . . . . ? B1 C1 C2 C3 174.4(2) . . . . ? B1 C1 C2 C5 -5.6(4) . . . . ? B1 C8 C13 C12 175.57(18) . . . . ? B1 C8 C13 C16 -2.0(3) . . . . ? C16 C13 C12 C11 -179.5(2) . . . . ? C15 C11 C12 C13 179.3(2) . . . . ?