#------------------------------------------------------------------------------ #$Date: 2026-06-12 23:11:39 +0100 (Fri, 12 Jun 2026) $ #$Revision: 306559 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577391.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_1577391 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 'C28 H27 B O' _chemical_formula_sum 'C28 H27 B O' _chemical_formula_weight 390.30 _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 2025-08-28 _audit_creation_method ; Olex2 1.5 (compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188) ; _audit_update_record ; 2025-08-28 deposited with the CCDC. 2026-06-11 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 108.852(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.7958(3) _cell_length_b 15.2749(4) _cell_length_c 14.0351(4) _cell_measurement_reflns_used 18679 _cell_measurement_temperature 276.36(10) _cell_measurement_theta_max 31.1260 _cell_measurement_theta_min 2.3880 _cell_volume 2190.30(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 air _diffrn_ambient_temperature 276.36(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 0.836 _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 -13.00 35.00 0.50 0.60 -- 6.13 -99.00-150.00 96 2 \w -57.00 -31.00 0.50 0.60 -- 6.13 -38.00-150.00 52 3 \w 4.00 75.00 0.50 0.60 -- 6.13 57.00-180.00 142 4 \w -17.00 9.00 0.50 0.60 -- 6.13 -38.00-150.00 52 5 \w -7.00 79.00 0.50 0.60 -- 6.13 38.00 -30.00 172 6 \w -9.00 75.00 0.50 0.60 -- 6.13 57.00 60.00 168 7 \w -16.00 28.00 0.50 0.60 -- -4.10 -99.00 60.00 88 ; _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 0.0460256000 _diffrn_orient_matrix_UB_12 0.0301611000 _diffrn_orient_matrix_UB_13 -0.0073872000 _diffrn_orient_matrix_UB_21 -0.0299688000 _diffrn_orient_matrix_UB_22 0.0342720000 _diffrn_orient_matrix_UB_23 0.0187745000 _diffrn_orient_matrix_UB_31 0.0424689000 _diffrn_orient_matrix_UB_32 -0.0084932000 _diffrn_orient_matrix_UB_33 0.0494362000 _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 0.0246 _diffrn_reflns_av_unetI/netI 0.0195 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.836 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 29449 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.836 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.132 _diffrn_reflns_theta_min 2.398 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Mova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.46736 _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 1.184 _exptl_crystal_description block _exptl_crystal_F_000 832 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.331 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 277 _refine_ls_number_reflns 5911 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.101 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0447 _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^)+(0.0732P)^2^+0.3968P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1293 _refine_ls_wR_factor_ref 0.1357 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4817 _reflns_number_total 5911 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc02310j2.cif _cod_data_source_block exp_3012-lh_auto _cod_database_code 1577391 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula 'C H B O' _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 0.993 _shelx_estimated_absorpt_t_min 0.993 _diffrn_oxdiff_digest_hkl ; 433f6366a6270c1d0ee93cb1a5a79b21509562 ; _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: C15(H15), C13(H13), C9(H9), C24(H24), C22(H22), C4(H4), C7(H7), C6(H6), C5(H5) 2.b Idealised Me refined as rotating group: C19(H19A,H19B,H19C), C26(H26A,H26B,H26C), C18(H18A,H18B,H18C), C28(H28A,H28B, H28C), C17(H17A,H17B,H17C), C27(H27A,H27B,H27C) ; _shelx_res_file ; TITL exp_3012-lh_auto_a.res in P2(1)/c exp_3012-lh_auto.res created by SHELXL-2019/3 at 13:37:54 on 28-Aug-2025 REM Old TITL REM SHELXT solution in P2(1)/c: R1 0.134, Rweak 0.019, Alpha 0.019 REM 0.399 for 182 systematic absences, Orientation as input REM Formula found by SHELXT: C29 O CELL 0.71073 10.7958 15.2749 14.0351 90 108.852 90 ZERR 4 0.0003 0.0004 0.0004 0 0.003 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H B O UNIT 112 108 4 4 L.S. 4 PLAN 2 SIZE 0.1 0.1 0.1 TEMP 3 CONF list 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.073200 0.396800 FVAR 0.55586 O1 4 0.505690 0.719247 0.638839 11.00000 0.03974 0.03629 = 0.02702 -0.00324 0.01202 0.00807 C12 1 0.775409 0.459316 0.600060 11.00000 0.02844 0.02945 = 0.02295 -0.00174 0.00996 -0.00201 C20 1 0.713639 0.593142 0.768017 11.00000 0.02763 0.02723 = 0.01968 -0.00268 0.00722 0.00148 C16 1 0.799662 0.562782 0.413472 11.00000 0.02974 0.03088 = 0.01900 -0.00282 0.00851 -0.00572 C2 1 0.552713 0.686689 0.495568 11.00000 0.02883 0.02737 = 0.02348 -0.00143 0.00616 -0.00133 C15 1 0.860469 0.486009 0.410032 11.00000 0.02767 0.03513 = 0.02370 -0.00467 0.01175 -0.00457 AFIX 43 H15 2 0.916648 0.486356 0.371858 11.00000 -1.20000 AFIX 0 C11 1 0.732275 0.544568 0.575330 11.00000 0.02663 0.02940 = 0.01846 -0.00263 0.00768 -0.00295 C21 1 0.621153 0.567558 0.813949 11.00000 0.03017 0.02831 = 0.02320 -0.00252 0.00893 -0.00007 C10 1 0.713930 0.583111 0.473494 11.00000 0.02826 0.02737 = 0.01890 -0.00351 0.00808 -0.00404 C25 1 0.835854 0.624456 0.829473 11.00000 0.02814 0.02954 = 0.02550 -0.00273 0.00726 0.00048 C1 1 0.579953 0.666282 0.596014 11.00000 0.03362 0.03070 = 0.02364 -0.00460 0.01045 0.00208 C13 1 0.807986 0.394392 0.537462 11.00000 0.02973 0.02542 = 0.02856 -0.00228 0.01176 -0.00231 AFIX 43 H13 2 0.798474 0.336646 0.554923 11.00000 -1.20000 AFIX 0 C3 1 0.453735 0.754053 0.471921 11.00000 0.02720 0.02747 = 0.03027 -0.00129 0.00650 -0.00211 C14 1 0.850479 0.404486 0.456817 11.00000 0.02519 0.03053 = 0.02718 -0.00516 0.00929 -0.00201 C9 1 0.625633 0.649599 0.437927 11.00000 0.03210 0.02986 = 0.01904 -0.00035 0.00720 -0.00244 AFIX 43 H9 2 0.613169 0.671144 0.373522 11.00000 -1.20000 AFIX 0 C24 1 0.862641 0.630203 0.933392 11.00000 0.03327 0.03302 = 0.02455 -0.00431 0.00075 -0.00088 AFIX 43 H24 2 0.944246 0.650182 0.973401 11.00000 -1.20000 AFIX 0 C22 1 0.650461 0.575112 0.917838 11.00000 0.03880 0.03169 = 0.02412 0.00016 0.01453 0.00221 AFIX 43 H22 2 0.588202 0.558526 0.947207 11.00000 -1.20000 AFIX 0 C8 1 0.429881 0.770878 0.562401 11.00000 0.03050 0.03003 = 0.03195 -0.00318 0.00755 -0.00009 C4 1 0.383888 0.800241 0.385204 11.00000 0.03033 0.03251 = 0.03437 0.00291 0.00574 -0.00185 AFIX 43 H4 2 0.398625 0.790561 0.324333 11.00000 -1.20000 AFIX 0 C23 1 0.770569 0.606855 0.978479 11.00000 0.04755 0.03132 = 0.01885 -0.00199 0.00742 0.00390 C7 1 0.339872 0.832265 0.571278 11.00000 0.03658 0.03457 = 0.04295 -0.00807 0.01313 0.00150 AFIX 43 H7 2 0.326649 0.843255 0.632451 11.00000 -1.20000 AFIX 0 C19 1 0.819828 0.635106 0.346210 11.00000 0.04834 0.03685 = 0.02945 0.00239 0.02054 -0.00181 AFIX 137 H19A 2 0.891511 0.620173 0.322897 11.00000 -1.50000 H19B 2 0.839044 0.688871 0.383527 11.00000 -1.50000 H19C 2 0.741719 0.642137 0.289553 11.00000 -1.50000 AFIX 0 C6 1 0.270545 0.876452 0.484110 11.00000 0.02952 0.03087 = 0.05612 -0.00300 0.00954 0.00183 AFIX 43 H6 2 0.208074 0.917550 0.486532 11.00000 -1.20000 AFIX 0 C26 1 0.490864 0.530154 0.751984 11.00000 0.03328 0.04473 = 0.03399 -0.00636 0.01185 -0.00853 AFIX 137 H26A 2 0.437704 0.575703 0.711870 11.00000 -1.50000 H26B 2 0.447558 0.505890 0.795878 11.00000 -1.50000 H26C 2 0.504326 0.485040 0.708727 11.00000 -1.50000 AFIX 0 C18 1 0.898993 0.325369 0.414873 11.00000 0.04499 0.03511 = 0.03711 -0.00466 0.02127 0.00283 AFIX 137 H18A 2 0.849221 0.318707 0.344941 11.00000 -1.50000 H18B 2 0.888827 0.274051 0.451133 11.00000 -1.50000 H18C 2 0.989771 0.333056 0.421882 11.00000 -1.50000 AFIX 0 C28 1 0.937721 0.653461 0.783625 11.00000 0.03042 0.04974 = 0.03811 -0.00437 0.01226 -0.00593 AFIX 137 H28A 2 0.969810 0.603467 0.757359 11.00000 -1.50000 H28B 2 1.008886 0.681196 0.834233 11.00000 -1.50000 H28C 2 0.899272 0.694172 0.730113 11.00000 -1.50000 AFIX 0 C5 1 0.292181 0.860786 0.392704 11.00000 0.02970 0.03376 = 0.04566 0.00416 0.00362 0.00028 AFIX 43 H5 2 0.243934 0.891698 0.335707 11.00000 -1.20000 AFIX 0 C17 1 0.786322 0.419639 0.701885 11.00000 0.06158 0.03244 = 0.02937 0.00498 0.02188 0.00867 AFIX 137 H17A 2 0.842371 0.455460 0.754469 11.00000 -1.50000 H17B 2 0.822464 0.361780 0.706262 11.00000 -1.50000 H17C 2 0.701015 0.416640 0.709175 11.00000 -1.50000 AFIX 0 C27 1 0.798453 0.616531 1.090455 11.00000 0.07029 0.05381 = 0.02088 -0.00490 0.01032 0.00044 AFIX 137 H27A 2 0.891363 0.617240 1.123735 11.00000 -1.50000 H27B 2 0.760578 0.568200 1.114976 11.00000 -1.50000 H27C 2 0.761160 0.670311 1.103898 11.00000 -1.50000 AFIX 0 B1 3 0.678573 0.598090 0.649793 11.00000 0.03000 0.02927 = 0.02054 -0.00308 0.00847 -0.00203 HKLF 4 REM exp_3012-lh_auto_a.res in P2(1)/c REM wR2 = 0.1357, GooF = S = 1.101, Restrained GooF = 1.101 for all data REM R1 = 0.0447 for 4817 Fo > 4sig(Fo) and 0.0543 for all 5911 data REM 277 parameters refined using 0 restraints END WGHT 0.0725 0.3984 REM Highest difference peak 0.331, deepest hole -0.201, 1-sigma level 0.041 Q1 1 0.7553 0.5721 0.4448 11.00000 0.05 0.33 Q2 1 0.6891 0.5659 0.6013 11.00000 0.05 0.30 ; _shelx_res_checksum 94600 _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 1.727 _oxdiff_exptl_absorpt_empirical_full_min 0.710 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 O1 O 0.50569(8) 0.71925(6) 0.63884(6) 0.0341(2) Uani 1 1 d . . . . . C12 C 0.77541(11) 0.45932(7) 0.60006(8) 0.0265(2) Uani 1 1 d . . . . . C20 C 0.71364(10) 0.59314(7) 0.76802(7) 0.0249(2) Uani 1 1 d . . . . . C16 C 0.79966(11) 0.56278(7) 0.41347(7) 0.0264(2) Uani 1 1 d . . . . . C2 C 0.55271(11) 0.68669(7) 0.49557(8) 0.0271(2) Uani 1 1 d . . . . . C15 C 0.86047(11) 0.48601(8) 0.41003(8) 0.0280(2) Uani 1 1 d . . . . . H15 H 0.916648 0.486356 0.371858 0.034 Uiso 1 1 calc R U . . . C11 C 0.73227(10) 0.54457(7) 0.57533(7) 0.0247(2) Uani 1 1 d . . . . . C21 C 0.62115(11) 0.56756(7) 0.81395(8) 0.0272(2) Uani 1 1 d . . . . . C10 C 0.71393(10) 0.58311(7) 0.47349(7) 0.0247(2) Uani 1 1 d . . . . . C25 C 0.83585(11) 0.62446(7) 0.82947(8) 0.0281(2) Uani 1 1 d . . . . . C1 C 0.57995(11) 0.66628(7) 0.59601(8) 0.0290(2) Uani 1 1 d . . . . . C13 C 0.80799(11) 0.39439(7) 0.53746(8) 0.0273(2) Uani 1 1 d . . . . . H13 H 0.798474 0.336646 0.554923 0.033 Uiso 1 1 calc R U . . . C3 C 0.45373(11) 0.75405(7) 0.47192(8) 0.0290(2) Uani 1 1 d . . . . . C14 C 0.85048(11) 0.40449(7) 0.45682(8) 0.0274(2) Uani 1 1 d . . . . . C9 C 0.62563(11) 0.64960(7) 0.43793(8) 0.0273(2) Uani 1 1 d . . . . . H9 H 0.613169 0.671144 0.373522 0.033 Uiso 1 1 calc R U . . . C24 C 0.86264(12) 0.63020(8) 0.93339(8) 0.0323(2) Uani 1 1 d . . . . . H24 H 0.944246 0.650182 0.973401 0.039 Uiso 1 1 calc R U . . . C22 C 0.65046(12) 0.57511(8) 0.91784(8) 0.0305(2) Uani 1 1 d . . . . . H22 H 0.588202 0.558526 0.947207 0.037 Uiso 1 1 calc R U . . . C8 C 0.42988(11) 0.77088(8) 0.56240(9) 0.0314(2) Uani 1 1 d . . . . . C4 C 0.38389(12) 0.80024(8) 0.38520(9) 0.0335(3) Uani 1 1 d . . . . . H4 H 0.398625 0.790561 0.324333 0.040 Uiso 1 1 calc R U . . . C23 C 0.77057(13) 0.60686(8) 0.97848(8) 0.0334(3) Uani 1 1 d . . . . . C7 C 0.33987(13) 0.83227(9) 0.57128(10) 0.0380(3) Uani 1 1 d . . . . . H7 H 0.326649 0.843255 0.632451 0.046 Uiso 1 1 calc R U . . . C19 C 0.81983(14) 0.63511(9) 0.34621(9) 0.0363(3) Uani 1 1 d . . . . . H19A H 0.891511 0.620173 0.322897 0.054 Uiso 1 1 calc R U . . . H19B H 0.839044 0.688871 0.383527 0.054 Uiso 1 1 calc R U . . . H19C H 0.741719 0.642137 0.289553 0.054 Uiso 1 1 calc R U . . . C6 C 0.27054(12) 0.87645(9) 0.48411(11) 0.0399(3) Uani 1 1 d . . . . . H6 H 0.208074 0.917550 0.486532 0.048 Uiso 1 1 calc R U . . . C26 C 0.49086(12) 0.53015(9) 0.75198(9) 0.0371(3) Uani 1 1 d . . . . . H26A H 0.437704 0.575703 0.711870 0.056 Uiso 1 1 calc R U . . . H26B H 0.447558 0.505890 0.795878 0.056 Uiso 1 1 calc R U . . . H26C H 0.504326 0.485040 0.708727 0.056 Uiso 1 1 calc R U . . . C18 C 0.89899(14) 0.32537(8) 0.41487(10) 0.0371(3) Uani 1 1 d . . . . . H18A H 0.849221 0.318707 0.344941 0.056 Uiso 1 1 calc R U . . . H18B H 0.888827 0.274051 0.451133 0.056 Uiso 1 1 calc R U . . . H18C H 0.989771 0.333056 0.421882 0.056 Uiso 1 1 calc R U . . . C28 C 0.93772(12) 0.65346(10) 0.78362(10) 0.0391(3) Uani 1 1 d . . . . . H28A H 0.969810 0.603467 0.757359 0.059 Uiso 1 1 calc R U . . . H28B H 1.008886 0.681196 0.834233 0.059 Uiso 1 1 calc R U . . . H28C H 0.899272 0.694172 0.730113 0.059 Uiso 1 1 calc R U . . . C5 C 0.29218(12) 0.86079(9) 0.39270(10) 0.0384(3) Uani 1 1 d . . . . . H5 H 0.243934 0.891698 0.335707 0.046 Uiso 1 1 calc R U . . . C17 C 0.78632(15) 0.41964(8) 0.70189(9) 0.0394(3) Uani 1 1 d . . . . . H17A H 0.842371 0.455460 0.754469 0.059 Uiso 1 1 calc R U . . . H17B H 0.822464 0.361780 0.706262 0.059 Uiso 1 1 calc R U . . . H17C H 0.701015 0.416640 0.709175 0.059 Uiso 1 1 calc R U . . . C27 C 0.79845(17) 0.61653(11) 1.09045(9) 0.0494(4) Uani 1 1 d . . . . . H27A H 0.891363 0.617240 1.123735 0.074 Uiso 1 1 calc R U . . . H27B H 0.760578 0.568200 1.114976 0.074 Uiso 1 1 calc R U . . . H27C H 0.761160 0.670311 1.103898 0.074 Uiso 1 1 calc R U . . . B1 B 0.67857(12) 0.59809(8) 0.64979(9) 0.0265(2) 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 O1 0.0397(5) 0.0363(4) 0.0270(4) -0.0032(3) 0.0120(3) 0.0081(4) C12 0.0284(5) 0.0294(5) 0.0230(5) -0.0017(4) 0.0100(4) -0.0020(4) C20 0.0276(5) 0.0272(5) 0.0197(4) -0.0027(4) 0.0072(4) 0.0015(4) C16 0.0297(5) 0.0309(5) 0.0190(4) -0.0028(4) 0.0085(4) -0.0057(4) C2 0.0288(5) 0.0274(5) 0.0235(5) -0.0014(4) 0.0062(4) -0.0013(4) C15 0.0277(5) 0.0351(6) 0.0237(5) -0.0047(4) 0.0117(4) -0.0046(4) C11 0.0266(5) 0.0294(5) 0.0185(4) -0.0026(4) 0.0077(4) -0.0029(4) C21 0.0302(5) 0.0283(5) 0.0232(5) -0.0025(4) 0.0089(4) -0.0001(4) C10 0.0283(5) 0.0274(5) 0.0189(4) -0.0035(4) 0.0081(4) -0.0040(4) C25 0.0281(5) 0.0295(5) 0.0255(5) -0.0027(4) 0.0073(4) 0.0005(4) C1 0.0336(6) 0.0307(5) 0.0236(5) -0.0046(4) 0.0105(4) 0.0021(4) C13 0.0297(5) 0.0254(5) 0.0286(5) -0.0023(4) 0.0118(4) -0.0023(4) C3 0.0272(5) 0.0275(5) 0.0303(5) -0.0013(4) 0.0065(4) -0.0021(4) C14 0.0252(5) 0.0305(5) 0.0272(5) -0.0052(4) 0.0093(4) -0.0020(4) C9 0.0321(5) 0.0299(5) 0.0190(4) -0.0004(4) 0.0072(4) -0.0024(4) C24 0.0333(6) 0.0330(6) 0.0245(5) -0.0043(4) 0.0007(4) -0.0009(5) C22 0.0388(6) 0.0317(6) 0.0241(5) 0.0002(4) 0.0145(4) 0.0022(5) C8 0.0305(6) 0.0300(6) 0.0320(6) -0.0032(4) 0.0076(4) -0.0001(4) C4 0.0303(6) 0.0325(6) 0.0344(6) 0.0029(5) 0.0057(5) -0.0019(5) C23 0.0475(7) 0.0313(6) 0.0189(5) -0.0020(4) 0.0074(4) 0.0039(5) C7 0.0366(6) 0.0346(6) 0.0430(7) -0.0081(5) 0.0131(5) 0.0015(5) C19 0.0483(7) 0.0368(6) 0.0295(6) 0.0024(5) 0.0205(5) -0.0018(5) C6 0.0295(6) 0.0309(6) 0.0561(8) -0.0030(5) 0.0095(5) 0.0018(5) C26 0.0333(6) 0.0447(7) 0.0340(6) -0.0064(5) 0.0119(5) -0.0085(5) C18 0.0450(7) 0.0351(6) 0.0371(6) -0.0047(5) 0.0213(5) 0.0028(5) C28 0.0304(6) 0.0497(7) 0.0381(6) -0.0044(5) 0.0123(5) -0.0059(5) C5 0.0297(6) 0.0338(6) 0.0457(7) 0.0042(5) 0.0036(5) 0.0003(5) C17 0.0616(8) 0.0324(6) 0.0294(6) 0.0050(5) 0.0219(6) 0.0087(6) C27 0.0703(10) 0.0538(8) 0.0209(5) -0.0049(5) 0.0103(6) 0.0004(7) B1 0.0300(6) 0.0293(6) 0.0205(5) -0.0031(4) 0.0085(4) -0.0020(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' O O 0.0106 0.0060 '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 C8 O1 C1 106.02(8) . . ? C11 C12 C13 128.37(10) . . ? C11 C12 C17 121.75(10) . . ? C13 C12 C17 109.77(10) . . ? C21 C20 B1 121.98(9) . . ? C25 C20 C21 118.51(9) . . ? C25 C20 B1 119.13(9) . . ? C15 C16 C10 127.27(10) . . ? C15 C16 C19 116.18(10) . . ? C10 C16 C19 116.53(10) . . ? C1 C2 C3 107.08(10) . . ? C1 C2 C9 121.26(10) . . ? C9 C2 C3 131.36(10) . . ? C16 C15 H15 115.5 . . ? C16 C15 C14 129.06(10) . . ? C14 C15 H15 115.5 . . ? C12 C11 C10 122.48(9) . . ? C12 C11 B1 119.06(9) . . ? C10 C11 B1 117.69(9) . . ? C20 C21 C26 120.59(9) . . ? C22 C21 C20 120.10(10) . . ? C22 C21 C26 119.30(10) . . ? C16 C10 C11 123.31(9) . . ? C9 C10 C16 116.07(9) . . ? C9 C10 C11 120.00(9) . . ? C20 C25 C28 120.45(10) . . ? C24 C25 C20 119.94(10) . . ? C24 C25 C28 119.60(10) . . ? O1 C1 B1 126.38(9) . . ? C2 C1 O1 110.16(10) . . ? C2 C1 B1 123.44(10) . . ? C12 C13 H13 115.0 . . ? C14 C13 C12 130.03(10) . . ? C14 C13 H13 115.0 . . ? C8 C3 C2 105.20(10) . . ? C4 C3 C2 135.33(11) . . ? C4 C3 C8 119.47(11) . . ? C15 C14 C18 115.55(10) . . ? C13 C14 C15 125.26(10) . . ? C13 C14 C18 119.10(10) . . ? C2 C9 H9 118.7 . . ? C10 C9 C2 122.50(10) . . ? C10 C9 H9 118.7 . . ? C25 C24 H24 119.2 . . ? C23 C24 C25 121.60(11) . . ? C23 C24 H24 119.2 . . ? C21 C22 H22 119.3 . . ? C23 C22 C21 121.45(11) . . ? C23 C22 H22 119.3 . . ? O1 C8 C3 111.51(10) . . ? O1 C8 C7 125.36(11) . . ? C7 C8 C3 123.13(11) . . ? C3 C4 H4 121.0 . . ? C5 C4 C3 117.97(12) . . ? C5 C4 H4 121.0 . . ? C24 C23 C22 118.38(10) . . ? C24 C23 C27 121.27(12) . . ? C22 C23 C27 120.34(12) . . ? C8 C7 H7 121.8 . . ? C8 C7 C6 116.42(12) . . ? C6 C7 H7 121.8 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C7 C6 H6 119.2 . . ? C7 C6 C5 121.63(12) . . ? C5 C6 H6 119.2 . . ? C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26B 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28B 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C4 C5 C6 121.37(12) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C23 C27 H27A 109.5 . . ? C23 C27 H27B 109.5 . . ? C23 C27 H27C 109.5 . . ? H27A C27 H27B 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C11 B1 C20 131.02(10) . . ? C1 B1 C20 116.75(9) . . ? C1 B1 C11 112.21(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 O1 C1 1.4036(13) . ? O1 C8 1.3694(14) . ? C12 C11 1.3888(16) . ? C12 C13 1.4418(15) . ? C12 C17 1.5214(15) . ? C20 C21 1.4075(15) . ? C20 C25 1.4065(15) . ? C20 B1 1.5800(15) . ? C16 C15 1.3524(16) . ? C16 C10 1.4719(14) . ? C16 C19 1.5139(15) . ? C2 C1 1.3796(15) . ? C2 C3 1.4428(16) . ? C2 C9 1.4166(15) . ? C15 H15 0.9300 . ? C15 C14 1.4280(16) . ? C11 C10 1.4986(14) . ? C11 B1 1.5774(15) . ? C21 C22 1.3933(14) . ? C21 C26 1.5069(16) . ? C10 C9 1.3718(16) . ? C25 C24 1.3950(15) . ? C25 C28 1.5090(16) . ? C1 B1 1.5063(17) . ? C13 H13 0.9300 . ? C13 C14 1.3605(15) . ? C3 C8 1.3987(16) . ? C3 C4 1.3981(16) . ? C14 C18 1.5102(16) . ? C9 H9 0.9300 . ? C24 H24 0.9300 . ? C24 C23 1.3864(18) . ? C22 H22 0.9300 . ? C22 C23 1.3884(18) . ? C8 C7 1.3846(17) . ? C4 H4 0.9300 . ? C4 C5 1.3834(18) . ? C23 C27 1.5089(16) . ? C7 H7 0.9300 . ? C7 C6 1.386(2) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C6 H6 0.9300 . ? C6 C5 1.397(2) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C5 H5 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 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 O1 C1 B1 C20 -7.48(17) . . . . ? O1 C1 B1 C11 174.02(10) . . . . ? O1 C8 C7 C6 -178.51(11) . . . . ? C12 C11 C10 C16 -35.79(16) . . . . ? C12 C11 C10 C9 153.56(11) . . . . ? C12 C11 B1 C20 29.61(17) . . . . ? C12 C11 B1 C1 -152.18(10) . . . . ? C12 C13 C14 C15 -6.4(2) . . . . ? C12 C13 C14 C18 169.96(11) . . . . ? C20 C21 C22 C23 -0.63(18) . . . . ? C20 C25 C24 C23 -0.95(18) . . . . ? C16 C15 C14 C13 -20.69(19) . . . . ? C16 C15 C14 C18 162.88(11) . . . . ? C16 C10 C9 C2 -168.87(10) . . . . ? C2 C1 B1 C20 170.82(10) . . . . ? C2 C1 B1 C11 -7.67(16) . . . . ? C2 C3 C8 O1 -0.19(13) . . . . ? C2 C3 C8 C7 -179.97(11) . . . . ? C2 C3 C4 C5 178.78(12) . . . . ? C15 C16 C10 C11 33.38(16) . . . . ? C15 C16 C10 C9 -155.63(11) . . . . ? C11 C12 C13 C14 26.4(2) . . . . ? C11 C10 C9 C2 2.44(16) . . . . ? C21 C20 C25 C24 -0.49(16) . . . . ? C21 C20 C25 C28 -179.42(11) . . . . ? C21 C20 B1 C11 -115.84(14) . . . . ? C21 C20 B1 C1 66.01(14) . . . . ? C21 C22 C23 C24 -0.79(18) . . . . ? C21 C22 C23 C27 178.43(12) . . . . ? C10 C16 C15 C14 4.92(19) . . . . ? C10 C11 B1 C20 -160.16(11) . . . . ? C10 C11 B1 C1 18.05(14) . . . . ? C25 C20 C21 C22 1.26(16) . . . . ? C25 C20 C21 C26 -177.52(11) . . . . ? C25 C20 B1 C11 71.45(16) . . . . ? C25 C20 B1 C1 -106.70(12) . . . . ? C25 C24 C23 C22 1.58(18) . . . . ? C25 C24 C23 C27 -177.63(12) . . . . ? C1 O1 C8 C3 -0.81(13) . . . . ? C1 O1 C8 C7 178.96(12) . . . . ? C1 C2 C3 C8 1.14(12) . . . . ? C1 C2 C3 C4 -178.29(13) . . . . ? C1 C2 C9 C10 9.23(17) . . . . ? C13 C12 C11 C10 -0.64(18) . . . . ? C13 C12 C11 B1 169.10(11) . . . . ? C3 C2 C1 O1 -1.69(13) . . . . ? C3 C2 C1 B1 179.77(11) . . . . ? C3 C2 C9 C10 -177.91(11) . . . . ? C3 C8 C7 C6 1.24(19) . . . . ? C3 C4 C5 C6 0.76(18) . . . . ? C9 C2 C1 O1 172.71(10) . . . . ? C9 C2 C1 B1 -5.83(18) . . . . ? C9 C2 C3 C8 -172.48(12) . . . . ? C9 C2 C3 C4 8.1(2) . . . . ? C8 O1 C1 C2 1.56(13) . . . . ? C8 O1 C1 B1 -179.95(11) . . . . ? C8 C3 C4 C5 -0.59(17) . . . . ? C8 C7 C6 C5 -1.05(19) . . . . ? C4 C3 C8 O1 179.35(10) . . . . ? C4 C3 C8 C7 -0.43(18) . . . . ? C7 C6 C5 C4 0.1(2) . . . . ? C19 C16 C15 C14 -173.60(11) . . . . ? C19 C16 C10 C11 -148.10(11) . . . . ? C19 C16 C10 C9 22.89(14) . . . . ? C26 C21 C22 C23 178.17(12) . . . . ? C28 C25 C24 C23 177.99(12) . . . . ? C17 C12 C11 C10 -176.58(11) . . . . ? C17 C12 C11 B1 -6.84(16) . . . . ? C17 C12 C13 C14 -157.24(13) . . . . ? B1 C20 C21 C22 -171.50(10) . . . . ? B1 C20 C21 C26 9.72(17) . . . . ? B1 C20 C25 C24 172.48(10) . . . . ? B1 C20 C25 C28 -6.45(16) . . . . ? B1 C11 C10 C16 154.34(10) . . . . ? B1 C11 C10 C9 -16.32(15) . . . . ?