#------------------------------------------------------------------------------ #$Date: 2026-06-12 23:11:39 +0100 (Fri, 12 Jun 2026) $ #$Revision: 306559 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577397.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_1577397 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 monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2025-05-30 _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 90 _cell_angle_beta 98.901(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.9864(5) _cell_length_b 14.6975(4) _cell_length_c 8.4759(3) _cell_measurement_reflns_used 13237 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 31.1170 _cell_measurement_theta_min 2.7530 _cell_volume 2090.59(11) _computing_cell_refinement 'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro 1.171.43.142a (Rigaku OD, 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 'SHELXT 2018/2 (Sheldrick, 2018)' _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 0.999 _diffrn_measured_fraction_theta_max 0.842 _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 2.00 28.00 0.50 1.00 -- -4.10 -99.00 150.00 52 2 \w -15.00 12.00 0.50 1.00 -- -4.10 -99.00 0.00 54 3 \w -65.00 9.00 0.50 1.00 -- -4.10 -38.00 -60.00 148 4 \w -3.00 76.00 0.50 1.00 -- 6.13 57.00-180.00 158 5 \w -15.00 66.00 0.50 1.00 -- -4.10 38.00 -90.00 162 6 \w -79.00 5.00 0.50 1.00 -- -4.10 -19.00 60.00 168 ; _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 -0.0419833000 _diffrn_orient_matrix_UB_12 0.0041495000 _diffrn_orient_matrix_UB_13 -0.0196201000 _diffrn_orient_matrix_UB_21 -0.0048797000 _diffrn_orient_matrix_UB_22 -0.0325699000 _diffrn_orient_matrix_UB_23 0.0594677000 _diffrn_orient_matrix_UB_31 0.0004369000 _diffrn_orient_matrix_UB_32 0.0353633000 _diffrn_orient_matrix_UB_33 0.0570693000 _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 0.0374 _diffrn_reflns_av_unetI/netI 0.0297 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.842 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 27045 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.842 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.779 _diffrn_reflns_theta_min 2.427 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Mova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.68656 _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 'dull dark violet' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary violet _exptl_crystal_density_diffrn 1.177 _exptl_crystal_description block _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.380 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.048 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 251 _refine_ls_number_reflns 5508 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.074 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0433 _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^)+(0.0657P)^2^+0.5102P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1186 _refine_ls_wR_factor_ref 0.1255 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4430 _reflns_number_total 5508 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc02310j2.cif _cod_data_source_block exp_2642-lh_auto _cod_database_code 1577397 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula 'C H B S ' _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_digest_hkl ; 43f629031caddf80a8c3c553169eb2003bc3fb ; _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: C6(H6), C12(H12), C10(H10), C21(H21), C3(H3), C19(H19) 2.b Idealised Me refined as rotating group: C16(H16A,H16B,H16C), C25(H25A,H25B,H25C), C5(H5A,H5B,H5C), C15(H15A,H15B, H15C), C24(H24A,H24B,H24C), C14(H14A,H14B,H14C), C23(H23A,H23B,H23C) ; _shelx_res_file ; TITL exp_2642-lh_auto_a.res in P2(1)/c exp_2642-lh_auto.res created by SHELXL-2019/3 at 21:36:20 on 30-May-2025 REM Old TITL REM SHELXT solution in P2(1)/c: R1 0.119, Rweak 0.013, Alpha 0.020 REM 0.366 for 181 systematic absences, Orientation as input REM Formula found by SHELXT: C26 S CELL 0.71073 16.9864 14.6975 8.4759 90 98.901 90 ZERR 4 0.0005 0.0004 0.0003 0 0.003 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H B S UNIT 100 108 4 4 L.S. 4 PLAN 5 SIZE 0.1 0.1 0.1 TEMP -123 CONF BOND list 4 fmap 2 MORE -1 BOND $H ACTA REM REM REM WGHT 0.065700 0.510200 FVAR 0.66654 S1 4 0.155510 0.431184 0.319729 11.00000 0.02843 0.03187 = 0.03075 -0.00127 0.00086 0.00718 C7 1 0.381860 0.394577 0.688874 11.00000 0.02461 0.01947 = 0.02346 0.00365 0.00720 0.00217 C13 1 0.465630 0.389667 0.768737 11.00000 0.02564 0.01997 = 0.02801 0.00212 0.00639 0.00183 C2 1 0.286689 0.357015 0.447572 11.00000 0.02638 0.02362 = 0.02326 0.00145 0.00779 0.00237 C17 1 0.195847 0.577106 0.624761 11.00000 0.02307 0.02069 = 0.02983 -0.00114 0.00609 0.00200 C22 1 0.119513 0.569108 0.667771 11.00000 0.02450 0.02328 = 0.03134 -0.00067 0.00678 -0.00083 C8 1 0.324285 0.460140 0.742637 11.00000 0.02440 0.01953 = 0.02676 -0.00107 0.00675 -0.00060 C20 1 0.103655 0.733518 0.664008 11.00000 0.02685 0.02532 = 0.03366 -0.00274 0.00161 0.00664 C6 1 0.361387 0.346266 0.550797 11.00000 0.02533 0.02253 = 0.02543 0.00110 0.00817 0.00488 AFIX 43 H6 2 0.398501 0.303423 0.521763 11.00000 -1.20000 AFIX 0 C12 1 0.490619 0.389196 0.928803 11.00000 0.02693 0.02303 = 0.03073 0.00171 0.00178 0.00002 AFIX 43 H12 2 0.546579 0.385845 0.962051 11.00000 -1.20000 AFIX 0 C18 1 0.223122 0.664641 0.592275 11.00000 0.02423 0.02374 = 0.03860 0.00144 0.00752 0.00000 C9 1 0.323238 0.476118 0.903482 11.00000 0.02652 0.02528 = 0.02931 -0.00390 0.00851 -0.00309 C1 1 0.236773 0.429454 0.470920 11.00000 0.02615 0.02387 = 0.02742 0.00073 0.00465 0.00373 C10 1 0.368340 0.428867 1.037576 11.00000 0.03677 0.02736 = 0.02453 -0.00187 0.00983 -0.00589 AFIX 43 H10 2 0.341885 0.421866 1.127716 11.00000 -1.20000 AFIX 0 C21 1 0.075026 0.646918 0.687248 11.00000 0.02082 0.03104 = 0.03560 -0.00241 0.00739 0.00228 AFIX 43 H21 2 0.023699 0.640449 0.717259 11.00000 -1.20000 AFIX 0 C4 1 0.186751 0.335181 0.229524 11.00000 0.03198 0.03239 = 0.02393 -0.00099 0.00654 0.00151 C11 1 0.442517 0.393163 1.053877 11.00000 0.03929 0.02038 = 0.02409 0.00057 0.00267 -0.00534 C3 1 0.257444 0.303734 0.309749 11.00000 0.03044 0.02829 = 0.02474 -0.00228 0.00780 0.00259 AFIX 43 H3 2 0.284351 0.251931 0.277408 11.00000 -1.20000 AFIX 0 C19 1 0.177174 0.740833 0.612846 11.00000 0.02961 0.01963 = 0.04343 0.00257 0.00527 0.00025 AFIX 43 H19 2 0.196630 0.799412 0.591308 11.00000 -1.20000 AFIX 0 C16 1 0.529009 0.385081 0.661657 11.00000 0.02561 0.03857 = 0.03176 0.00228 0.00660 0.00365 AFIX 137 H16A 2 0.521782 0.329563 0.596999 11.00000 -1.50000 H16B 2 0.581821 0.384370 0.727357 11.00000 -1.50000 H16C 2 0.524469 0.438338 0.591264 11.00000 -1.50000 AFIX 0 C25 1 0.085570 0.477225 0.701419 11.00000 0.03485 0.02826 = 0.05320 0.00190 0.01632 -0.00487 AFIX 137 H25A 2 0.052680 0.454281 0.604360 11.00000 -1.50000 H25B 2 0.052797 0.483319 0.786368 11.00000 -1.50000 H25C 2 0.129245 0.434550 0.735329 11.00000 -1.50000 AFIX 0 C5 1 0.137513 0.296176 0.083124 11.00000 0.03949 0.05071 = 0.02922 -0.00810 0.00006 0.00314 AFIX 137 H5A 2 0.082198 0.289642 0.101261 11.00000 -1.50000 H5B 2 0.158652 0.236419 0.060032 11.00000 -1.50000 H5C 2 0.139495 0.336968 -0.007639 11.00000 -1.50000 AFIX 0 C15 1 0.482881 0.364397 1.217152 11.00000 0.05374 0.03238 = 0.02587 0.00353 0.00038 -0.00174 AFIX 137 H15A 2 0.500106 0.300900 1.213430 11.00000 -1.50000 H15B 2 0.445441 0.370311 1.293679 11.00000 -1.50000 H15C 2 0.529348 0.403270 1.250539 11.00000 -1.50000 AFIX 0 C24 1 0.057787 0.817565 0.696650 11.00000 0.03634 0.03125 = 0.05385 -0.00588 0.00442 0.01245 AFIX 137 H24A 2 0.002445 0.801027 0.702717 11.00000 -1.50000 H24B 2 0.058941 0.861620 0.610248 11.00000 -1.50000 H24C 2 0.082183 0.844641 0.798188 11.00000 -1.50000 AFIX 0 C14 1 0.268391 0.545753 0.962820 11.00000 0.03900 0.04823 = 0.03350 -0.01459 0.00719 0.00875 AFIX 137 H14A 2 0.260988 0.597347 0.888764 11.00000 -1.50000 H14B 2 0.292193 0.567193 1.069021 11.00000 -1.50000 H14C 2 0.216654 0.517588 0.968909 11.00000 -1.50000 AFIX 0 C23 1 0.302518 0.677022 0.535472 11.00000 0.03246 0.03509 = 0.07476 0.01116 0.02287 0.00131 AFIX 137 H23A 2 0.342555 0.638396 0.598861 11.00000 -1.50000 H23B 2 0.318929 0.740865 0.548074 11.00000 -1.50000 H23C 2 0.297545 0.659830 0.422651 11.00000 -1.50000 AFIX 0 B1 3 0.252378 0.492463 0.614093 11.00000 0.02441 0.02039 = 0.03039 0.00088 0.01005 0.00134 HKLF 4 REM exp_2642-lh_auto_a.res in P2(1)/c REM wR2 = 0.1255, GooF = S = 1.074, Restrained GooF = 1.074 for all data REM R1 = 0.0433 for 4430 Fo > 4sig(Fo) and 0.0570 for all 5508 data REM 251 parameters refined using 0 restraints END WGHT 0.0656 0.5138 REM Highest difference peak 0.380, deepest hole -0.251, 1-sigma level 0.048 Q1 1 0.2228 0.5363 0.6148 11.00000 0.05 0.38 Q2 1 0.3278 0.6200 0.5183 11.00000 0.05 0.34 Q3 1 0.2768 0.3353 0.3754 11.00000 0.05 0.31 Q4 1 0.2513 0.4648 0.5263 11.00000 0.05 0.31 Q5 1 0.1691 0.3763 0.2570 11.00000 0.05 0.30 ; _shelx_res_checksum 6916 _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 1.761 _oxdiff_exptl_absorpt_empirical_full_min 0.643 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 S1 S 0.15551(2) 0.43118(2) 0.31973(4) 0.03074(11) Uani 1 1 d . . . . . C7 C 0.38186(8) 0.39458(8) 0.68887(15) 0.0221(3) Uani 1 1 d . . . . . C13 C 0.46563(8) 0.38967(8) 0.76874(16) 0.0243(3) Uani 1 1 d . . . . . C2 C 0.28669(8) 0.35702(9) 0.44757(15) 0.0240(3) Uani 1 1 d . . . . . C17 C 0.19585(8) 0.57711(8) 0.62476(16) 0.0243(3) Uani 1 1 d . . . . . C22 C 0.11951(8) 0.56911(9) 0.66777(17) 0.0261(3) Uani 1 1 d . . . . . C8 C 0.32429(8) 0.46014(8) 0.74264(15) 0.0233(3) Uani 1 1 d . . . . . C20 C 0.10365(8) 0.73352(9) 0.66401(17) 0.0289(3) Uani 1 1 d . . . . . C6 C 0.36139(8) 0.34627(8) 0.55080(15) 0.0240(3) Uani 1 1 d . . . . . H6 H 0.398501 0.303423 0.521763 0.029 Uiso 1 1 calc R U . . . C12 C 0.49062(8) 0.38920(9) 0.92880(16) 0.0272(3) Uani 1 1 d . . . . . H12 H 0.546579 0.385845 0.962051 0.033 Uiso 1 1 calc R U . . . C18 C 0.22312(8) 0.66464(9) 0.59227(18) 0.0286(3) Uani 1 1 d . . . . . C9 C 0.32324(8) 0.47612(9) 0.90348(16) 0.0266(3) Uani 1 1 d . . . . . C1 C 0.23677(8) 0.42945(9) 0.47092(16) 0.0258(3) Uani 1 1 d . . . . . C10 C 0.36834(9) 0.42887(9) 1.03758(16) 0.0290(3) Uani 1 1 d . . . . . H10 H 0.341885 0.421866 1.127716 0.035 Uiso 1 1 calc R U . . . C21 C 0.07503(8) 0.64692(9) 0.68725(17) 0.0288(3) Uani 1 1 d . . . . . H21 H 0.023699 0.640449 0.717259 0.035 Uiso 1 1 calc R U . . . C4 C 0.18675(9) 0.33518(9) 0.22952(16) 0.0292(3) Uani 1 1 d . . . . . C11 C 0.44252(9) 0.39316(8) 1.05388(16) 0.0282(3) Uani 1 1 d . . . . . C3 C 0.25744(8) 0.30373(9) 0.30975(16) 0.0274(3) Uani 1 1 d . . . . . H3 H 0.284351 0.251931 0.277408 0.033 Uiso 1 1 calc R U . . . C19 C 0.17717(8) 0.74083(9) 0.61285(18) 0.0309(3) Uani 1 1 d . . . . . H19 H 0.196630 0.799412 0.591308 0.037 Uiso 1 1 calc R U . . . C16 C 0.52901(8) 0.38508(10) 0.66166(17) 0.0318(3) Uani 1 1 d . . . . . H16A H 0.521782 0.329563 0.596999 0.048 Uiso 1 1 calc R U . . . H16B H 0.581821 0.384370 0.727357 0.048 Uiso 1 1 calc R U . . . H16C H 0.524469 0.438338 0.591264 0.048 Uiso 1 1 calc R U . . . C25 C 0.08557(9) 0.47723(10) 0.7014(2) 0.0378(4) Uani 1 1 d . . . . . H25A H 0.052680 0.454281 0.604360 0.057 Uiso 1 1 calc R U . . . H25B H 0.052797 0.483319 0.786368 0.057 Uiso 1 1 calc R U . . . H25C H 0.129245 0.434550 0.735329 0.057 Uiso 1 1 calc R U . . . C5 C 0.13751(10) 0.29618(12) 0.08312(19) 0.0404(4) Uani 1 1 d . . . . . H5A H 0.082198 0.289642 0.101261 0.061 Uiso 1 1 calc R U . . . H5B H 0.158652 0.236419 0.060032 0.061 Uiso 1 1 calc R U . . . H5C H 0.139495 0.336968 -0.007639 0.061 Uiso 1 1 calc R U . . . C15 C 0.48288(11) 0.36440(10) 1.21715(18) 0.0379(3) Uani 1 1 d . . . . . H15A H 0.500106 0.300900 1.213430 0.057 Uiso 1 1 calc R U . . . H15B H 0.445441 0.370311 1.293679 0.057 Uiso 1 1 calc R U . . . H15C H 0.529348 0.403270 1.250539 0.057 Uiso 1 1 calc R U . . . C24 C 0.05779(10) 0.81756(11) 0.6966(2) 0.0407(4) Uani 1 1 d . . . . . H24A H 0.002445 0.801027 0.702717 0.061 Uiso 1 1 calc R U . . . H24B H 0.058941 0.861620 0.610248 0.061 Uiso 1 1 calc R U . . . H24C H 0.082183 0.844641 0.798188 0.061 Uiso 1 1 calc R U . . . C14 C 0.26839(10) 0.54575(12) 0.96282(19) 0.0401(4) Uani 1 1 d . . . . . H14A H 0.260988 0.597347 0.888764 0.060 Uiso 1 1 calc R U . . . H14B H 0.292193 0.567193 1.069021 0.060 Uiso 1 1 calc R U . . . H14C H 0.216654 0.517588 0.968909 0.060 Uiso 1 1 calc R U . . . C23 C 0.30252(10) 0.67702(11) 0.5355(3) 0.0459(4) Uani 1 1 d . . . . . H23A H 0.342555 0.638396 0.598861 0.069 Uiso 1 1 calc R U . . . H23B H 0.318929 0.740865 0.548074 0.069 Uiso 1 1 calc R U . . . H23C H 0.297545 0.659830 0.422651 0.069 Uiso 1 1 calc R U . . . B1 B 0.25238(9) 0.49246(9) 0.61409(18) 0.0245(3) 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 S1 0.02843(19) 0.03187(19) 0.03075(19) -0.00127(13) 0.00086(14) 0.00718(13) C7 0.0246(6) 0.0195(5) 0.0235(6) 0.0037(4) 0.0072(5) 0.0022(4) C13 0.0256(6) 0.0200(5) 0.0280(6) 0.0021(5) 0.0064(5) 0.0018(5) C2 0.0264(6) 0.0236(6) 0.0233(6) 0.0015(5) 0.0078(5) 0.0024(5) C17 0.0231(6) 0.0207(6) 0.0298(7) -0.0011(5) 0.0061(5) 0.0020(5) C22 0.0245(6) 0.0233(6) 0.0313(7) -0.0007(5) 0.0068(5) -0.0008(5) C8 0.0244(6) 0.0195(5) 0.0268(6) -0.0011(5) 0.0068(5) -0.0006(5) C20 0.0268(7) 0.0253(6) 0.0337(7) -0.0027(5) 0.0016(5) 0.0066(5) C6 0.0253(6) 0.0225(6) 0.0254(6) 0.0011(5) 0.0082(5) 0.0049(5) C12 0.0269(7) 0.0230(6) 0.0307(7) 0.0017(5) 0.0018(5) 0.0000(5) C18 0.0242(7) 0.0237(6) 0.0386(8) 0.0014(5) 0.0075(6) 0.0000(5) C9 0.0265(7) 0.0253(6) 0.0293(7) -0.0039(5) 0.0085(5) -0.0031(5) C1 0.0261(7) 0.0239(6) 0.0274(6) 0.0007(5) 0.0046(5) 0.0037(5) C10 0.0368(8) 0.0274(6) 0.0245(6) -0.0019(5) 0.0098(6) -0.0059(5) C21 0.0208(6) 0.0310(7) 0.0356(7) -0.0024(5) 0.0074(5) 0.0023(5) C4 0.0320(7) 0.0324(7) 0.0239(6) -0.0010(5) 0.0065(5) 0.0015(5) C11 0.0393(8) 0.0204(6) 0.0241(6) 0.0006(5) 0.0027(6) -0.0053(5) C3 0.0304(7) 0.0283(6) 0.0247(6) -0.0023(5) 0.0078(5) 0.0026(5) C19 0.0296(7) 0.0196(6) 0.0434(8) 0.0026(5) 0.0053(6) 0.0002(5) C16 0.0256(7) 0.0386(7) 0.0318(7) 0.0023(6) 0.0066(6) 0.0037(6) C25 0.0348(8) 0.0283(7) 0.0532(10) 0.0019(6) 0.0163(7) -0.0049(6) C5 0.0395(8) 0.0507(9) 0.0292(7) -0.0081(7) 0.0001(6) 0.0031(7) C15 0.0537(10) 0.0324(7) 0.0259(7) 0.0035(6) 0.0004(7) -0.0017(7) C24 0.0363(8) 0.0313(7) 0.0539(10) -0.0059(7) 0.0044(7) 0.0125(6) C14 0.0390(9) 0.0482(9) 0.0335(8) -0.0146(7) 0.0072(6) 0.0088(7) C23 0.0325(8) 0.0351(8) 0.0748(12) 0.0112(8) 0.0229(8) 0.0013(6) B1 0.0244(7) 0.0204(6) 0.0304(7) 0.0009(5) 0.0100(6) 0.0013(5) 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 92.94(7) . . ? C13 C7 C8 121.37(11) . . ? C6 C7 C13 117.74(11) . . ? C6 C7 C8 120.30(11) . . ? C7 C13 C16 116.79(11) . . ? C12 C13 C7 125.96(12) . . ? C12 C13 C16 117.24(12) . . ? C1 C2 C6 119.84(12) . . ? C1 C2 C3 113.09(12) . . ? C3 C2 C6 126.92(12) . . ? C22 C17 C18 118.14(11) . . ? C22 C17 B1 122.78(11) . . ? C18 C17 B1 119.07(11) . . ? C17 C22 C25 121.17(12) . . ? C21 C22 C17 120.05(12) . . ? C21 C22 C25 118.71(12) . . ? C7 C8 B1 117.18(11) . . ? C9 C8 C7 121.20(12) . . ? C9 C8 B1 120.09(11) . . ? C21 C20 C19 117.87(12) . . ? C21 C20 C24 121.52(13) . . ? C19 C20 C24 120.60(13) . . ? C7 C6 C2 123.29(11) . . ? C7 C6 H6 118.4 . . ? C2 C6 H6 118.4 . . ? C13 C12 H12 116.1 . . ? C13 C12 C11 127.72(13) . . ? C11 C12 H12 116.1 . . ? C17 C18 C23 120.58(12) . . ? C19 C18 C17 120.18(12) . . ? C19 C18 C23 119.24(12) . . ? C8 C9 C10 127.28(12) . . ? C8 C9 C14 122.75(13) . . ? C10 C9 C14 109.90(12) . . ? C2 C1 S1 109.80(10) . . ? C2 C1 B1 123.02(12) . . ? B1 C1 S1 127.12(10) . . ? C9 C10 H10 115.2 . . ? C11 C10 C9 129.69(13) . . ? C11 C10 H10 115.2 . . ? C22 C21 H21 119.1 . . ? C20 C21 C22 121.82(12) . . ? C20 C21 H21 119.1 . . ? C3 C4 S1 111.27(10) . . ? C3 C4 C5 128.15(13) . . ? C5 C4 S1 120.57(11) . . ? C12 C11 C15 115.88(13) . . ? C10 C11 C12 124.60(13) . . ? C10 C11 C15 119.15(13) . . ? C2 C3 H3 123.6 . . ? C4 C3 C2 112.89(12) . . ? C4 C3 H3 123.6 . . ? C20 C19 C18 121.74(12) . . ? C20 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? 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 . . ? 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 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5B 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 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 . . ? 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 . . ? 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 . . ? 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 . . ? C8 B1 C17 127.48(12) . . ? C1 B1 C17 119.55(12) . . ? C1 B1 C8 112.90(11) . . ? 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 1.7323(14) . ? S1 C4 1.7270(14) . ? C7 C13 1.4799(18) . ? C7 C8 1.4935(17) . ? C7 C6 1.3671(18) . ? C13 C12 1.3575(19) . ? C13 C16 1.5132(18) . ? C2 C6 1.4342(18) . ? C2 C1 1.3941(18) . ? C2 C3 1.4301(18) . ? C17 C22 1.4051(19) . ? C17 C18 1.4090(18) . ? C17 B1 1.5827(18) . ? C22 C21 1.3945(18) . ? C22 C25 1.5127(18) . ? C8 C9 1.3862(18) . ? C8 B1 1.579(2) . ? C20 C21 1.3874(19) . ? C20 C19 1.388(2) . ? C20 C24 1.5087(18) . ? C6 H6 0.9500 . ? C12 H12 0.9500 . ? C12 C11 1.4363(19) . ? C18 C19 1.3913(18) . ? C18 C23 1.512(2) . ? C9 C10 1.446(2) . ? C9 C14 1.5210(19) . ? C1 B1 1.517(2) . ? C10 H10 0.9500 . ? C10 C11 1.352(2) . ? C21 H21 0.9500 . ? C4 C3 1.366(2) . ? C4 C5 1.499(2) . ? C11 C15 1.5068(19) . ? C3 H3 0.9500 . ? C19 H19 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? 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 B1 C17 -7.40(19) . . . . ? S1 C1 B1 C8 169.78(10) . . . . ? S1 C4 C3 C2 0.76(16) . . . . ? C7 C13 C12 C11 0.1(2) . . . . ? C7 C8 C9 C10 -6.6(2) . . . . ? C7 C8 C9 C14 176.87(13) . . . . ? C7 C8 B1 C17 -163.94(12) . . . . ? C7 C8 B1 C1 19.15(16) . . . . ? C13 C7 C8 C9 -40.72(18) . . . . ? C13 C7 C8 B1 153.37(11) . . . . ? C13 C7 C6 C2 -168.99(11) . . . . ? C13 C12 C11 C10 -24.2(2) . . . . ? C13 C12 C11 C15 162.79(13) . . . . ? C2 C1 B1 C17 175.73(12) . . . . ? C2 C1 B1 C8 -7.10(18) . . . . ? C17 C22 C21 C20 0.5(2) . . . . ? C17 C18 C19 C20 -0.5(2) . . . . ? C22 C17 C18 C19 4.1(2) . . . . ? C22 C17 C18 C23 -176.16(15) . . . . ? C22 C17 B1 C8 -99.73(17) . . . . ? C22 C17 B1 C1 77.00(18) . . . . ? C8 C7 C13 C12 44.95(18) . . . . ? C8 C7 C13 C16 -134.83(12) . . . . ? C8 C7 C6 C2 2.31(19) . . . . ? C8 C9 C10 C11 34.3(2) . . . . ? C6 C7 C13 C12 -143.84(13) . . . . ? C6 C7 C13 C16 36.37(16) . . . . ? C6 C7 C8 C9 148.30(13) . . . . ? C6 C7 C8 B1 -17.62(17) . . . . ? C6 C2 C1 S1 174.87(10) . . . . ? C6 C2 C1 B1 -7.8(2) . . . . ? C6 C2 C3 C4 -175.36(13) . . . . ? C18 C17 C22 C21 -4.1(2) . . . . ? C18 C17 C22 C25 178.86(14) . . . . ? C18 C17 B1 C8 79.31(18) . . . . ? C18 C17 B1 C1 -103.97(15) . . . . ? C9 C8 B1 C17 30.0(2) . . . . ? C9 C8 B1 C1 -146.92(12) . . . . ? C9 C10 C11 C12 -5.4(2) . . . . ? C9 C10 C11 C15 167.41(13) . . . . ? C1 S1 C4 C3 -1.15(11) . . . . ? C1 S1 C4 C5 178.19(13) . . . . ? C1 C2 C6 C7 11.05(19) . . . . ? C1 C2 C3 C4 0.17(17) . . . . ? C21 C20 C19 C18 -3.0(2) . . . . ? C4 S1 C1 C2 1.22(11) . . . . ? C4 S1 C1 B1 -175.99(13) . . . . ? C3 C2 C6 C7 -173.69(13) . . . . ? C3 C2 C1 S1 -1.01(14) . . . . ? C3 C2 C1 B1 176.34(12) . . . . ? C19 C20 C21 C22 3.0(2) . . . . ? C16 C13 C12 C11 179.85(12) . . . . ? C25 C22 C21 C20 177.68(14) . . . . ? C5 C4 C3 C2 -178.51(14) . . . . ? C24 C20 C21 C22 -175.57(14) . . . . ? C24 C20 C19 C18 175.58(14) . . . . ? C14 C9 C10 C11 -148.78(15) . . . . ? C23 C18 C19 C20 179.70(15) . . . . ? B1 C17 C22 C21 174.97(13) . . . . ? B1 C17 C22 C25 -2.1(2) . . . . ? B1 C17 C18 C19 -175.00(13) . . . . ? B1 C17 C18 C23 4.8(2) . . . . ? B1 C8 C9 C10 158.90(13) . . . . ? B1 C8 C9 C14 -17.6(2) . . . . ?