#------------------------------------------------------------------------------ #$Date: 2026-06-12 23:11:39 +0100 (Fri, 12 Jun 2026) $ #$Revision: 306559 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577394.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_1577394 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 'C24 H25 B S' _chemical_formula_sum 'C24 H25 B S' _chemical_formula_weight 356.31 _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 iterative _audit_creation_date 2025-05-04 _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 85.126(3) _cell_angle_beta 80.824(3) _cell_angle_gamma 66.849(4) _cell_formula_units_Z 2 _cell_length_a 8.0595(3) _cell_length_b 8.1715(3) _cell_length_c 17.1081(6) _cell_measurement_reflns_used 7443 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 28.9930 _cell_measurement_theta_min 2.4020 _cell_volume 1022.41(7) _computing_cell_refinement 'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro system (CCD 43.142a 64-bit (release 17-10-2024))' _computing_data_reduction 'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)' _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 'olex2.solve 1.5 (Bourhis et al., 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.00(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.962 _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 -25.00 61.00 0.50 0.90 -- -20.24 19.00 60.00 172 2 \w -14.00 53.00 0.50 0.90 -- -20.24 19.00 -30.00 134 3 \w -38.00 30.00 0.50 0.90 -- -20.24 89.00-100.00 136 4 \w -25.00 10.00 0.50 0.90 -- -20.24 19.00-180.00 70 5 \w 22.00 50.00 0.50 0.90 -- -20.24 19.00-180.00 56 6 \w -73.00 24.00 0.50 0.90 -- 22.51 -19.00-180.00 194 7 \w -37.00 76.00 0.50 0.90 -- 22.51 -89.00 143.00 226 8 \w 67.00 104.00 0.50 0.90 -- 22.51 178.00 120.00 74 9 \w -4.00 33.00 0.50 0.90 -- 22.51 89.00-100.00 74 10 \w -28.00 11.00 0.50 0.90 -- -20.24 -89.00 143.00 78 11 \w -10.00 35.00 0.50 0.90 -- -20.24 -99.00 0.00 90 12 \w -8.00 18.00 0.50 0.90 -- -20.24 -99.00 -60.00 52 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0305116000 _diffrn_orient_matrix_UB_12 0.0095384000 _diffrn_orient_matrix_UB_13 0.0353635000 _diffrn_orient_matrix_UB_21 -0.0889251000 _diffrn_orient_matrix_UB_22 0.0608671000 _diffrn_orient_matrix_UB_23 0.0139135000 _diffrn_orient_matrix_UB_31 -0.0223538000 _diffrn_orient_matrix_UB_32 -0.0715665000 _diffrn_orient_matrix_UB_33 0.0179072000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_unetI/netI 0.0387 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.962 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 11814 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.962 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.484 _diffrn_reflns_theta_min 2.413 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Mova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.162 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.79839 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear whiteish colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier whiteish _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.157 _exptl_crystal_description block _exptl_crystal_F_000 380 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.421 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.065 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 241 _refine_ls_number_reflns 4529 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0570 _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^)+(0.0917P)^2^+0.5211P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1638 _refine_ls_wR_factor_ref 0.1718 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3694 _reflns_number_total 4529 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc02310j2.cif _cod_data_source_block jd44lhj3-1_auto _cod_database_code 1577394 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula 'C H S B ' _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 0.984 _shelx_estimated_absorpt_t_min 0.984 _diffrn_oxdiff_ac3_digest_hkl 41c015c893d2b54b7b22f961d3660c89720ddd _diffrn_oxdiff_digest_hkl ; 43099a8454004e81a7d8a6706f3814fbc88934 ; _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: C9(H9), C11(H11), C18(H18), C20(H20), C3(H3), C4(H4) 2.b Idealised Me refined as rotating group: C14(H14A,H14B,H14C), C22(H22A,H22B,H22C), C13(H13A,H13B,H13C), C24(H24A,H24B, H24C), C15(H15A,H15B,H15C), C23(H23A,H23B,H23C) 2.c : C6(H6) ; _shelx_res_file ; TITL jd44lhj3-1_auto_a.res in P-1 jd44lhj3-1_auto.res created by SHELXL-2019/3 at 18:04:35 on 04-May-2025 REM Old TITL REM SHELXT solution in P-1: R1 0.141, Rweak 0.007, Alpha 0.026 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C25 S CELL 0.71073 8.0595 8.1715 17.1081 85.126 80.824 66.849 ZERR 2 0.0003 0.0003 0.0006 0.003 0.003 0.004 LATT 1 SFAC C H B S UNIT 48 50 2 2 L.S. 4 PLAN 5 SIZE 0.1 0.1 0.1 TEMP -123 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta SHEL 999 0.77 OMIT -1 2 0 OMIT -1 3 1 OMIT 0 3 1 OMIT 0 4 1 OMIT 3 4 2 OMIT 3 5 3 REM REM REM WGHT 0.091700 0.521100 FVAR 0.88828 S1 4 0.566457 0.256841 0.335997 11.00000 0.04329 0.03497 = 0.03092 0.00421 -0.00733 -0.01267 C7 1 0.348806 0.694174 0.179911 11.00000 0.02060 0.02548 = 0.02496 -0.00189 -0.00031 -0.00890 C16 1 0.252704 0.646495 0.341146 11.00000 0.02581 0.02612 = 0.02311 0.00054 -0.00345 -0.01048 C8 1 0.325593 0.614458 0.114778 11.00000 0.02478 0.02868 = 0.02509 -0.00201 -0.00164 -0.01128 C5 1 0.774752 0.464858 0.150961 11.00000 0.02656 0.03871 = 0.03115 -0.00889 -0.00592 -0.00960 C12 1 0.338036 0.871772 0.170134 11.00000 0.02662 0.02744 = 0.03002 -0.00255 -0.00113 -0.01012 C21 1 0.071243 0.657922 0.347647 11.00000 0.02775 0.02962 = 0.02830 -0.00094 -0.00220 -0.01224 C9 1 0.289142 0.710845 0.044072 11.00000 0.02945 0.03516 = 0.02562 -0.00221 -0.00389 -0.01293 AFIX 43 H9 2 0.271729 0.655583 0.001127 11.00000 -1.20000 AFIX 0 C17 1 0.310189 0.683440 0.409201 11.00000 0.02867 0.03334 = 0.02530 0.00021 -0.00437 -0.01251 C11 1 0.304706 0.962228 0.098078 11.00000 0.03424 0.02636 = 0.03586 0.00332 -0.00246 -0.01317 AFIX 43 H11 2 0.300391 1.080429 0.092128 11.00000 -1.20000 AFIX 0 C19 1 0.013154 0.739423 0.485915 11.00000 0.03677 0.03046 = 0.02664 -0.00015 0.00355 -0.01341 C1 1 0.562417 0.419427 0.263102 11.00000 0.02886 0.03134 = 0.02441 -0.00151 -0.00672 -0.01081 C10 1 0.277509 0.884992 0.034486 11.00000 0.02878 0.03538 = 0.02909 0.00576 -0.00505 -0.01076 C18 1 0.188873 0.730959 0.479473 11.00000 0.03899 0.03639 = 0.02321 -0.00111 -0.00502 -0.01500 AFIX 43 H18 2 0.228969 0.758240 0.524142 11.00000 -1.20000 AFIX 0 C20 1 -0.043851 0.701572 0.419514 11.00000 0.02644 0.03738 = 0.03256 -0.00127 0.00169 -0.01486 AFIX 43 H20 2 -0.164220 0.705522 0.423155 11.00000 -1.20000 AFIX 0 C2 1 0.728909 0.362070 0.214131 11.00000 0.02867 0.03761 = 0.02859 -0.00731 -0.00504 -0.00995 C14 1 0.333667 0.426465 0.118424 11.00000 0.04000 0.03304 = 0.02925 -0.00319 -0.00491 -0.01849 AFIX 137 H14A 2 0.394790 0.361622 0.163347 11.00000 -1.50000 H14B 2 0.401760 0.366771 0.069193 11.00000 -1.50000 H14C 2 0.209699 0.428841 0.125102 11.00000 -1.50000 AFIX 0 C22 1 0.497899 0.682603 0.409159 11.00000 0.03382 0.04993 = 0.03120 -0.00626 -0.00758 -0.01926 AFIX 137 H22A 2 0.577878 0.623067 0.361881 11.00000 -1.50000 H22B 2 0.547596 0.618792 0.456663 11.00000 -1.50000 H22C 2 0.490044 0.805406 0.408905 11.00000 -1.50000 AFIX 0 C3 1 0.853182 0.191477 0.236409 11.00000 0.03082 0.04334 = 0.04064 -0.00895 -0.00766 -0.00028 AFIX 43 H3 2 0.972761 0.134449 0.209266 11.00000 -1.20000 AFIX 0 C13 1 0.372632 0.962263 0.235613 11.00000 0.05359 0.03461 = 0.03564 -0.00210 -0.00846 -0.02301 AFIX 137 H13A 2 0.296882 0.951083 0.284970 11.00000 -1.50000 H13B 2 0.342026 1.088540 0.221503 11.00000 -1.50000 H13C 2 0.501433 0.905872 0.242847 11.00000 -1.50000 AFIX 0 C24 1 -0.002431 0.617610 0.279150 11.00000 0.03091 0.06318 = 0.03491 -0.00772 -0.00174 -0.02599 AFIX 137 H24A 2 0.019561 0.688125 0.232380 11.00000 -1.50000 H24B 2 -0.133676 0.647881 0.292971 11.00000 -1.50000 H24C 2 0.058959 0.490635 0.267601 11.00000 -1.50000 AFIX 0 C15 1 0.236787 0.987396 -0.042805 11.00000 0.04816 0.04335 = 0.03637 0.01240 -0.01187 -0.01636 AFIX 137 H15A 2 0.248722 0.905198 -0.083815 11.00000 -1.50000 H15B 2 0.322986 1.045556 -0.058832 11.00000 -1.50000 H15C 2 0.112286 1.077739 -0.035814 11.00000 -1.50000 AFIX 0 B1 3 0.387344 0.589558 0.261252 11.00000 0.02360 0.02824 = 0.02609 -0.00253 -0.00382 -0.01379 C23 1 -0.116175 0.788946 0.562645 11.00000 0.04976 0.04827 = 0.03088 -0.00413 0.01093 -0.01836 AFIX 137 H23A 2 -0.047143 0.781088 0.606041 11.00000 -1.50000 H23B 2 -0.179301 0.706878 0.573705 11.00000 -1.50000 H23C 2 -0.205732 0.910906 0.557818 11.00000 -1.50000 AFIX 0 C6 1 0.829067 0.545711 0.096924 11.00000 0.04632 0.05577 = 0.03966 -0.00418 0.00312 -0.02372 AFIX 163 H6 2 0.871520 0.608906 0.054689 11.00000 -1.20000 AFIX 0 C4 1 0.782382 0.119601 0.300388 11.00000 0.04980 0.03479 = 0.04369 -0.00059 -0.01482 0.00077 AFIX 43 H4 2 0.845640 0.005763 0.322906 11.00000 -1.20000 AFIX 0 HKLF 4 REM jd44lhj3-1_auto_a.res in P-1 REM wR2 = 0.1718, GooF = S = 1.067, Restrained GooF = 1.067 for all data REM R1 = 0.0570 for 3694 Fo > 4sig(Fo) and 0.0677 for all 4529 data REM 241 parameters refined using 0 restraints END WGHT 0.0917 0.5216 REM Highest difference peak 0.421, deepest hole -0.246, 1-sigma level 0.065 Q1 1 0.6725 0.1688 0.3289 11.00000 0.05 0.42 Q2 1 0.4883 0.5164 0.2588 11.00000 0.05 0.40 Q3 1 0.6392 0.2821 0.2789 11.00000 0.05 0.40 Q4 1 0.7776 0.4638 0.1223 11.00000 0.05 0.33 Q5 1 0.2302 0.8171 0.0479 11.00000 0.05 0.33 ; _shelx_res_checksum 88464 _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 1.283 _oxdiff_exptl_absorpt_empirical_full_min 0.752 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 0.56646(8) 0.25684(7) 0.33600(3) 0.03720(18) Uani 1 1 d . . . . . C7 C 0.3488(2) 0.6942(2) 0.17991(11) 0.0239(4) Uani 1 1 d . . . . . C16 C 0.2527(3) 0.6465(2) 0.34115(10) 0.0249(4) Uani 1 1 d . . . . . C8 C 0.3256(3) 0.6145(3) 0.11478(11) 0.0260(4) Uani 1 1 d . . . . . C5 C 0.7748(3) 0.4649(3) 0.15096(12) 0.0323(4) Uani 1 1 d . . . . . C12 C 0.3380(3) 0.8718(3) 0.17013(11) 0.0283(4) Uani 1 1 d . . . . . C21 C 0.0712(3) 0.6579(3) 0.34765(11) 0.0284(4) Uani 1 1 d . . . . . C9 C 0.2891(3) 0.7108(3) 0.04407(11) 0.0298(4) Uani 1 1 d . . . . . H9 H 0.271729 0.655583 0.001127 0.036 Uiso 1 1 calc R U . . . C17 C 0.3102(3) 0.6834(3) 0.40920(11) 0.0289(4) Uani 1 1 d . . . . . C11 C 0.3047(3) 0.9622(3) 0.09808(12) 0.0322(4) Uani 1 1 d . . . . . H11 H 0.300391 1.080429 0.092128 0.039 Uiso 1 1 calc R U . . . C19 C 0.0132(3) 0.7394(3) 0.48592(12) 0.0321(4) Uani 1 1 d . . . . . C1 C 0.5624(3) 0.4194(3) 0.26310(11) 0.0280(4) Uani 1 1 d . . . . . C10 C 0.2775(3) 0.8850(3) 0.03449(12) 0.0319(4) Uani 1 1 d . . . . . C18 C 0.1889(3) 0.7310(3) 0.47947(11) 0.0326(4) Uani 1 1 d . . . . . H18 H 0.228969 0.758240 0.524142 0.039 Uiso 1 1 calc R U . . . C20 C -0.0439(3) 0.7016(3) 0.41951(12) 0.0320(4) Uani 1 1 d . . . . . H20 H -0.164220 0.705522 0.423155 0.038 Uiso 1 1 calc R U . . . C2 C 0.7289(3) 0.3621(3) 0.21413(12) 0.0320(4) Uani 1 1 d . . . . . C14 C 0.3337(3) 0.4265(3) 0.11842(12) 0.0326(4) Uani 1 1 d . . . . . H14A H 0.394790 0.361622 0.163347 0.049 Uiso 1 1 calc R U . . . H14B H 0.401760 0.366771 0.069193 0.049 Uiso 1 1 calc R U . . . H14C H 0.209699 0.428841 0.125102 0.049 Uiso 1 1 calc R U . . . C22 C 0.4979(3) 0.6826(3) 0.40916(13) 0.0367(5) Uani 1 1 d . . . . . H22A H 0.577878 0.623067 0.361881 0.055 Uiso 1 1 calc R U . . . H22B H 0.547596 0.618792 0.456663 0.055 Uiso 1 1 calc R U . . . H22C H 0.490044 0.805406 0.408905 0.055 Uiso 1 1 calc R U . . . C3 C 0.8532(3) 0.1915(3) 0.23641(14) 0.0418(5) Uani 1 1 d . . . . . H3 H 0.972761 0.134449 0.209266 0.050 Uiso 1 1 calc R U . . . C13 C 0.3726(4) 0.9623(3) 0.23561(13) 0.0391(5) Uani 1 1 d . . . . . H13A H 0.296882 0.951083 0.284970 0.059 Uiso 1 1 calc R U . . . H13B H 0.342026 1.088540 0.221503 0.059 Uiso 1 1 calc R U . . . H13C H 0.501433 0.905872 0.242847 0.059 Uiso 1 1 calc R U . . . C24 C -0.0024(3) 0.6176(4) 0.27915(13) 0.0405(5) Uani 1 1 d . . . . . H24A H 0.019561 0.688125 0.232380 0.061 Uiso 1 1 calc R U . . . H24B H -0.133676 0.647881 0.292971 0.061 Uiso 1 1 calc R U . . . H24C H 0.058959 0.490635 0.267601 0.061 Uiso 1 1 calc R U . . . C15 C 0.2368(4) 0.9874(3) -0.04281(14) 0.0432(6) Uani 1 1 d . . . . . H15A H 0.248722 0.905198 -0.083815 0.065 Uiso 1 1 calc R U . . . H15B H 0.322986 1.045556 -0.058832 0.065 Uiso 1 1 calc R U . . . H15C H 0.112286 1.077739 -0.035814 0.065 Uiso 1 1 calc R U . . . B1 B 0.3873(3) 0.5896(3) 0.26125(12) 0.0246(4) Uani 1 1 d . . . . . C23 C -0.1162(4) 0.7889(3) 0.56264(13) 0.0449(6) Uani 1 1 d . . . . . H23A H -0.047143 0.781088 0.606041 0.067 Uiso 1 1 calc R U . . . H23B H -0.179301 0.706878 0.573705 0.067 Uiso 1 1 calc R U . . . H23C H -0.205732 0.910906 0.557818 0.067 Uiso 1 1 calc R U . . . C6 C 0.8291(4) 0.5457(4) 0.09692(15) 0.0469(6) Uani 1 1 d . . . . . H6 H 0.871520 0.608906 0.054689 0.056 Uiso 1 1 calc R U . . . C4 C 0.7824(4) 0.1196(3) 0.30039(15) 0.0471(6) Uani 1 1 d . . . . . H4 H 0.845640 0.005763 0.322906 0.057 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 0.0433(3) 0.0350(3) 0.0309(3) 0.0042(2) -0.0073(2) -0.0127(2) C7 0.0206(9) 0.0255(9) 0.0250(9) -0.0019(7) -0.0003(7) -0.0089(7) C16 0.0258(9) 0.0261(9) 0.0231(9) 0.0005(7) -0.0035(7) -0.0105(8) C8 0.0248(9) 0.0287(10) 0.0251(9) -0.0020(7) -0.0016(7) -0.0113(8) C5 0.0266(10) 0.0387(11) 0.0312(10) -0.0089(8) -0.0059(8) -0.0096(9) C12 0.0266(10) 0.0274(10) 0.0300(10) -0.0025(7) -0.0011(7) -0.0101(8) C21 0.0278(10) 0.0296(10) 0.0283(10) -0.0009(7) -0.0022(8) -0.0122(8) C9 0.0295(10) 0.0352(11) 0.0256(9) -0.0022(7) -0.0039(8) -0.0129(9) C17 0.0287(10) 0.0333(10) 0.0253(9) 0.0002(7) -0.0044(8) -0.0125(8) C11 0.0342(11) 0.0264(10) 0.0359(11) 0.0033(8) -0.0025(8) -0.0132(9) C19 0.0368(11) 0.0305(10) 0.0266(10) -0.0001(7) 0.0035(8) -0.0134(9) C1 0.0289(10) 0.0313(10) 0.0244(9) -0.0015(7) -0.0067(7) -0.0108(8) C10 0.0288(10) 0.0354(11) 0.0291(10) 0.0058(8) -0.0051(8) -0.0108(9) C18 0.0390(12) 0.0364(11) 0.0232(9) -0.0011(8) -0.0050(8) -0.0150(9) C20 0.0264(10) 0.0374(11) 0.0326(10) -0.0013(8) 0.0017(8) -0.0149(9) C2 0.0287(10) 0.0376(11) 0.0286(10) -0.0073(8) -0.0050(8) -0.0100(9) C14 0.0400(12) 0.0330(11) 0.0292(10) -0.0032(8) -0.0049(8) -0.0185(9) C22 0.0338(11) 0.0499(13) 0.0312(11) -0.0063(9) -0.0076(8) -0.0193(10) C3 0.0308(11) 0.0433(13) 0.0406(12) -0.0089(10) -0.0077(9) -0.0003(10) C13 0.0536(14) 0.0346(11) 0.0356(11) -0.0021(9) -0.0085(10) -0.0230(11) C24 0.0309(11) 0.0632(15) 0.0349(11) -0.0077(10) -0.0017(9) -0.0260(11) C15 0.0482(14) 0.0434(13) 0.0364(12) 0.0124(9) -0.0119(10) -0.0164(11) B1 0.0236(10) 0.0282(11) 0.0261(10) -0.0025(8) -0.0038(8) -0.0138(9) C23 0.0498(14) 0.0483(14) 0.0309(11) -0.0041(9) 0.0109(10) -0.0184(12) C6 0.0463(14) 0.0558(15) 0.0397(13) -0.0042(11) 0.0031(10) -0.0237(12) C4 0.0498(15) 0.0348(12) 0.0437(13) -0.0006(10) -0.0148(11) 0.0008(11) 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 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 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 93.03(11) . . ? C8 C7 C12 117.93(17) . . ? C8 C7 B1 121.47(16) . . ? C12 C7 B1 120.60(16) . . ? C21 C16 C17 117.59(17) . . ? C21 C16 B1 121.00(16) . . ? C17 C16 B1 121.39(17) . . ? C7 C8 C14 122.56(17) . . ? C9 C8 C7 120.21(17) . . ? C9 C8 C14 117.21(17) . . ? C6 C5 C2 174.7(2) . . ? C7 C12 C13 120.94(17) . . ? C11 C12 C7 120.03(18) . . ? C11 C12 C13 118.94(18) . . ? C16 C21 C24 121.81(17) . . ? C20 C21 C16 120.32(18) . . ? C20 C21 C24 117.84(18) . . ? C8 C9 H9 119.0 . . ? C10 C9 C8 121.97(18) . . ? C10 C9 H9 119.0 . . ? C16 C17 C22 122.76(17) . . ? C18 C17 C16 120.17(18) . . ? C18 C17 C22 117.01(17) . . ? C12 C11 H11 119.0 . . ? C10 C11 C12 122.00(18) . . ? C10 C11 H11 119.0 . . ? C18 C19 C20 118.11(18) . . ? C18 C19 C23 121.5(2) . . ? C20 C19 C23 120.3(2) . . ? C2 C1 S1 108.77(15) . . ? C2 C1 B1 132.07(19) . . ? B1 C1 S1 119.14(14) . . ? C9 C10 C11 117.83(18) . . ? C9 C10 C15 121.0(2) . . ? C11 C10 C15 121.16(19) . . ? C17 C18 H18 119.0 . . ? C19 C18 C17 122.07(18) . . ? C19 C18 H18 119.0 . . ? C21 C20 H20 119.1 . . ? C19 C20 C21 121.72(19) . . ? C19 C20 H20 119.1 . . ? C5 C2 C3 122.7(2) . . ? C1 C2 C5 123.7(2) . . ? C1 C2 C3 113.5(2) . . ? C8 C14 H14A 109.5 . . ? C8 C14 H14B 109.5 . . ? C8 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C2 C3 H3 123.7 . . ? C4 C3 C2 112.6(2) . . ? C4 C3 H3 123.7 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C7 B1 C16 123.34(17) . . ? C1 B1 C7 118.79(16) . . ? C1 B1 C16 117.85(17) . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C5 C6 H6 180.0 . . ? S1 C4 H4 123.9 . . ? C3 C4 S1 112.12(18) . . ? C3 C4 H4 123.9 . . ? 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 1.737(2) . ? S1 C4 1.703(3) . ? C7 C8 1.409(3) . ? C7 C12 1.416(3) . ? C7 B1 1.578(3) . ? C16 C21 1.415(3) . ? C16 C17 1.415(3) . ? C16 B1 1.581(3) . ? C8 C9 1.393(3) . ? C8 C14 1.508(3) . ? C5 C2 1.404(3) . ? C5 C6 1.215(3) . ? C12 C11 1.390(3) . ? C12 C13 1.511(3) . ? C21 C20 1.396(3) . ? C21 C24 1.509(3) . ? C9 H9 0.9500 . ? C9 C10 1.386(3) . ? C17 C18 1.399(3) . ? C17 C22 1.510(3) . ? C11 H11 0.9500 . ? C11 C10 1.390(3) . ? C19 C18 1.377(3) . ? C19 C20 1.391(3) . ? C19 C23 1.515(3) . ? C1 C2 1.391(3) . ? C1 B1 1.546(3) . ? C10 C15 1.514(3) . ? C18 H18 0.9500 . ? C20 H20 0.9500 . ? C2 C3 1.423(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C3 H3 0.9500 . ? C3 C4 1.350(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C6 H6 0.9500 . ? C4 H4 0.9500 . ? 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 C5 -177.17(16) . . . . ? S1 C1 C2 C3 -0.1(2) . . . . ? S1 C1 B1 C7 -153.99(14) . . . . ? S1 C1 B1 C16 24.2(2) . . . . ? C7 C8 C9 C10 1.1(3) . . . . ? C7 C12 C11 C10 1.3(3) . . . . ? C16 C21 C20 C19 1.7(3) . . . . ? C16 C17 C18 C19 1.6(3) . . . . ? C8 C7 C12 C11 0.3(3) . . . . ? C8 C7 C12 C13 -176.31(18) . . . . ? C8 C7 B1 C16 -116.5(2) . . . . ? C8 C7 B1 C1 61.7(2) . . . . ? C8 C9 C10 C11 0.4(3) . . . . ? C8 C9 C10 C15 -179.7(2) . . . . ? C5 C2 C3 C4 177.8(2) . . . . ? C12 C7 C8 C9 -1.4(3) . . . . ? C12 C7 C8 C14 -179.80(18) . . . . ? C12 C7 B1 C16 64.1(2) . . . . ? C12 C7 B1 C1 -117.8(2) . . . . ? C12 C11 C10 C9 -1.6(3) . . . . ? C12 C11 C10 C15 178.5(2) . . . . ? C21 C16 C17 C18 -0.6(3) . . . . ? C21 C16 C17 C22 -177.65(18) . . . . ? C21 C16 B1 C7 59.0(3) . . . . ? C21 C16 B1 C1 -119.2(2) . . . . ? C17 C16 C21 C20 -1.0(3) . . . . ? C17 C16 C21 C24 -178.76(19) . . . . ? C17 C16 B1 C7 -122.6(2) . . . . ? C17 C16 B1 C1 59.2(2) . . . . ? C1 S1 C4 C3 0.8(2) . . . . ? C1 C2 C3 C4 0.6(3) . . . . ? C18 C19 C20 C21 -0.7(3) . . . . ? C20 C19 C18 C17 -0.9(3) . . . . ? C2 C1 B1 C7 24.1(3) . . . . ? C2 C1 B1 C16 -157.6(2) . . . . ? C2 C3 C4 S1 -0.9(3) . . . . ? C14 C8 C9 C10 179.57(19) . . . . ? C22 C17 C18 C19 178.81(19) . . . . ? C13 C12 C11 C10 177.9(2) . . . . ? C24 C21 C20 C19 179.5(2) . . . . ? B1 C7 C8 C9 179.08(18) . . . . ? B1 C7 C8 C14 0.7(3) . . . . ? B1 C7 C12 C11 179.75(18) . . . . ? B1 C7 C12 C13 3.2(3) . . . . ? B1 C16 C21 C20 177.47(18) . . . . ? B1 C16 C21 C24 -0.3(3) . . . . ? B1 C16 C17 C18 -179.04(18) . . . . ? B1 C16 C17 C22 3.9(3) . . . . ? B1 C1 C2 C5 4.6(3) . . . . ? B1 C1 C2 C3 -178.3(2) . . . . ? C23 C19 C18 C17 179.3(2) . . . . ? C23 C19 C20 C21 179.1(2) . . . . ? C4 S1 C1 C2 -0.40(16) . . . . ? C4 S1 C1 B1 178.14(16) . . . . ?