#------------------------------------------------------------------------------ #$Date: 2026-06-12 23:11:39 +0100 (Fri, 12 Jun 2026) $ #$Revision: 306559 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577392.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_1577392 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 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 _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 91.103(2) _cell_angle_beta 101.962(2) _cell_angle_gamma 98.061(2) _cell_formula_units_Z 2 _cell_length_a 8.2330(5) _cell_length_b 11.8475(8) _cell_length_c 11.8841(8) _cell_measurement_reflns_used 9420 _cell_measurement_temperature 293.00(10) _cell_measurement_theta_max 27.21 _cell_measurement_theta_min 2.41 _cell_volume 1121.41(13) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _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 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 293.00(10) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0553 _diffrn_reflns_av_unetI/netI 0.0335 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 30669 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.478 _diffrn_reflns_theta_min 2.557 _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6338 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1509 before and 0.0664 after correction. The Ratio of minimum to maximum transmission is 0.8501. The \l/2 correction factor is Not present. ; _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 1.156 _exptl_crystal_description block _exptl_crystal_F_000 416 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.252 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.065 _refine_ls_extinction_coef 0.198(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 278 _refine_ls_number_reflns 5128 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0601 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1037P)^2^+0.2387P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1636 _refine_ls_wR_factor_ref 0.1936 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3672 _reflns_number_total 5128 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc02310j2.cif _cod_data_source_block a_a _cod_original_sg_symbol_H-M P-1 _cod_database_code 1577392 _shelx_shelxl_version_number 2019/3 _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 _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: C13(H00B), C15(H00C), C24(H00D), C22(H00H), C6(H00K), C7(H00O), C9(H00P), C8(H00Z) 2.b Idealised Me refined as rotating group: C19(H00A,H00E,H00F), C28(H00G,H00I,H00J), C18(H00L,H00M,H00N), C26(H00Q,H00R, H00S), C17(H00U,H00V,H00W), C27(H00X,H00Y,H) 2.c : C4(H00T) ; _shelx_res_file ; TITL A_a.res in P-1 a_a.res created by SHELXL-2019/3 at 14:43:47 on 05-Jun-2025 REM Old TITL A in P-1 REM SHELXT solution in P-1 REM R1 0.180, Rweak 0.005, Alpha 0.041, Orientation as input REM Formula found by SHELXT: C28 O2 CELL 0.71073 8.233 11.8475 11.8841 91.103 101.962 98.061 ZERR 2 0.0005 0.0008 0.0008 0.002 0.002 0.002 LATT 1 SFAC C H B O UNIT 56 54 2 2 L.S. 10 PLAN 4 SIZE 0.1 0.1 0.1 TEMP 19.85(10) CONF LIST 6 MORE -1 BOND $H fmap 2 acta SHEL 999 0.77 OMIT -1 0 1 OMIT 1 -1 1 REM REM REM WGHT 0.103700 0.238700 EXTI 0.198188 FVAR 1.52172 O1 4 0.072290 0.680340 0.093505 11.00000 0.06237 0.06945 = 0.04606 -0.00417 0.00867 0.01358 C11 1 0.265530 0.738458 0.422253 11.00000 0.05132 0.05226 = 0.04629 0.00374 0.00881 0.01162 C2 1 0.034806 0.834332 0.194675 11.00000 0.05091 0.06120 = 0.04635 0.00170 0.01207 0.00671 C1 1 0.114984 0.739920 0.200500 11.00000 0.05358 0.06120 = 0.04375 -0.00205 0.01178 0.00646 C20 1 0.382940 0.632352 0.250791 11.00000 0.04994 0.05462 = 0.04735 0.00077 0.01054 0.00529 C16 1 0.127051 0.712975 0.474934 11.00000 0.05451 0.05927 = 0.04735 0.00504 0.01147 0.01196 C25 1 0.415502 0.527150 0.296026 11.00000 0.05514 0.05482 = 0.05224 -0.00099 0.00886 0.00488 C10 1 -0.033755 0.739476 0.021672 11.00000 0.04889 0.07071 = 0.04661 0.00321 0.00969 0.00618 C12 1 0.413379 0.802764 0.487401 11.00000 0.05210 0.05566 = 0.05445 0.00039 0.00695 0.01198 C3 1 0.042337 0.917114 0.284099 11.00000 0.06936 0.06592 = 0.05200 0.00164 0.00958 0.01602 C13 1 0.417049 0.842307 0.599136 11.00000 0.06163 0.06089 = 0.05420 -0.00446 -0.00143 0.01394 AFIX 43 H00B 2 0.514006 0.886812 0.640328 11.00000 -1.20000 AFIX 0 C15 1 0.138532 0.751392 0.587786 11.00000 0.06414 0.06851 = 0.04879 0.00487 0.01636 0.01824 AFIX 43 H00C 2 0.047290 0.731984 0.622048 11.00000 -1.20000 AFIX 0 C24 1 0.533939 0.469670 0.259669 11.00000 0.06257 0.05491 = 0.06708 -0.00317 0.01067 0.01030 AFIX 43 H00D 2 0.554647 0.400298 0.290634 11.00000 -1.20000 AFIX 0 C5 1 -0.059475 0.836556 0.078390 11.00000 0.04555 0.06325 = 0.04823 0.00576 0.01163 0.00411 C21 1 0.470819 0.676592 0.167485 11.00000 0.05616 0.06218 = 0.05456 0.00208 0.01683 0.00612 C23 1 0.621121 0.513530 0.178690 11.00000 0.05358 0.06660 = 0.06884 -0.01429 0.01327 0.00658 C22 1 0.587198 0.616262 0.133433 11.00000 0.05596 0.07199 = 0.06144 -0.00342 0.02117 0.00333 AFIX 43 H00H 2 0.644153 0.646147 0.078265 11.00000 -1.20000 AFIX 0 C19 1 -0.034874 0.642036 0.413084 11.00000 0.05734 0.08808 = 0.05924 0.00236 0.01670 -0.00331 AFIX 137 H00A 2 -0.103516 0.689960 0.366408 11.00000 -1.50000 H00E 2 -0.093643 0.607646 0.468535 11.00000 -1.50000 H00F 2 -0.010420 0.583398 0.364982 11.00000 -1.50000 AFIX 0 C14 1 0.281276 0.817600 0.650922 11.00000 0.07408 0.06485 = 0.04811 -0.00113 0.00526 0.02471 C6 1 -0.161341 0.910196 0.018175 11.00000 0.05358 0.07292 = 0.05890 0.00969 0.01073 0.00937 AFIX 43 H00K 2 -0.180401 0.976049 0.054102 11.00000 -1.20000 AFIX 0 C28 1 0.320595 0.471027 0.380658 11.00000 0.07945 0.06122 = 0.06868 0.01221 0.02380 0.01100 AFIX 137 H00G 2 0.332287 0.522515 0.446164 11.00000 -1.50000 H00I 2 0.365031 0.402742 0.405263 11.00000 -1.50000 H00J 2 0.203996 0.452063 0.344471 11.00000 -1.50000 AFIX 0 C18 1 0.290024 0.861371 0.772253 11.00000 0.09512 0.09925 = 0.05341 -0.01432 0.01014 0.02291 AFIX 137 H00L 2 0.376316 0.830180 0.824076 11.00000 -1.50000 H00M 2 0.183983 0.838675 0.793036 11.00000 -1.50000 H00N 2 0.315348 0.943144 0.776942 11.00000 -1.50000 AFIX 0 C7 1 -0.231957 0.882117 -0.095283 11.00000 0.05776 0.09159 = 0.06109 0.01484 0.00367 0.01007 AFIX 43 H00O 2 -0.298056 0.930735 -0.137437 11.00000 -1.20000 AFIX 0 C9 1 -0.108029 0.708560 -0.092210 11.00000 0.06809 0.09371 = 0.05051 -0.00975 0.00535 0.01172 AFIX 43 H00P 2 -0.091678 0.641774 -0.127918 11.00000 -1.20000 AFIX 0 C26 1 0.449845 0.790275 0.115993 11.00000 0.08241 0.07687 = 0.07741 0.02096 0.03635 0.01212 AFIX 137 H00Q 2 0.349058 0.782114 0.057122 11.00000 -1.50000 H00R 2 0.544574 0.816488 0.083026 11.00000 -1.50000 H00S 2 0.442543 0.844635 0.175031 11.00000 -1.50000 AFIX 0 C4 1 0.040169 0.988913 0.353125 11.00000 0.11569 0.08354 = 0.06629 -0.01118 0.01107 0.03344 AFIX 163 H00T 2 0.038454 1.045748 0.407766 11.00000 -1.20000 AFIX 0 C17 1 0.568372 0.834939 0.439204 11.00000 0.05925 0.08754 = 0.08004 -0.01086 0.01589 -0.00536 AFIX 137 H00U 2 0.606976 0.766966 0.416460 11.00000 -1.50000 H00V 2 0.654715 0.878210 0.496989 11.00000 -1.50000 H00W 2 0.542039 0.880112 0.373500 11.00000 -1.50000 AFIX 0 C27 1 0.749732 0.451527 0.140426 11.00000 0.07276 0.08468 = 0.09925 -0.01748 0.02703 0.01906 AFIX 137 H00X 2 0.789525 0.400768 0.198420 11.00000 -1.50000 H00Y 2 0.842148 0.505914 0.128951 11.00000 -1.50000 H 2 0.699425 0.408414 0.069538 11.00000 -1.50000 AFIX 0 C8 1 -0.207131 0.782166 -0.149302 11.00000 0.06826 0.11030 = 0.05073 0.00240 -0.00144 0.00800 AFIX 43 H00Z 2 -0.259256 0.765049 -0.226127 11.00000 -1.20000 AFIX 0 B1 3 0.254561 0.700579 0.293249 11.00000 0.05065 0.05003 = 0.04791 0.00341 0.01165 0.00274 HKLF 4 REM A_a.res in P-1 REM wR2 = 0.1936, GooF = S = 1.023, Restrained GooF = 1.023 for all data REM R1 = 0.0601 for 3672 Fo > 4sig(Fo) and 0.0829 for all 5128 data REM 278 parameters refined using 0 restraints END WGHT 0.1037 0.2386 REM Highest difference peak 0.252, deepest hole -0.218, 1-sigma level 0.065 Q1 1 0.5625 0.7984 0.3370 11.00000 0.05 0.25 Q2 1 0.5822 0.8576 0.1708 11.00000 0.05 0.25 Q3 1 0.2238 0.9348 0.7777 11.00000 0.05 0.20 Q4 1 -0.1465 0.6590 0.4556 11.00000 0.05 0.20 ; _shelx_res_checksum 81691 _olex2_submission_special_instructions 'No special instructions were received' 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 O1 O 0.07229(16) 0.68034(11) 0.09351(10) 0.0594(3) Uani 1 1 d . . . . . C11 C 0.2655(2) 0.73846(14) 0.42225(13) 0.0498(4) Uani 1 1 d . . . . . C2 C 0.0348(2) 0.83433(15) 0.19468(14) 0.0527(4) Uani 1 1 d . . . . . C1 C 0.1150(2) 0.73992(15) 0.20050(13) 0.0529(4) Uani 1 1 d . . . . . C20 C 0.3829(2) 0.63235(14) 0.25079(13) 0.0509(4) Uani 1 1 d . . . . . C16 C 0.1271(2) 0.71298(15) 0.47493(14) 0.0532(4) Uani 1 1 d . . . . . C25 C 0.4155(2) 0.52715(14) 0.29603(14) 0.0548(4) Uani 1 1 d . . . . . C10 C -0.0338(2) 0.73948(16) 0.02167(14) 0.0557(4) Uani 1 1 d . . . . . C12 C 0.4134(2) 0.80276(15) 0.48740(15) 0.0543(4) Uani 1 1 d . . . . . C3 C 0.0423(2) 0.91711(16) 0.28410(15) 0.0623(5) Uani 1 1 d . . . . . C13 C 0.4170(2) 0.84231(16) 0.59914(15) 0.0605(5) Uani 1 1 d . . . . . H00B H 0.514006 0.886812 0.640328 0.073 Uiso 1 1 calc R U . . . C15 C 0.1385(2) 0.75139(16) 0.58779(15) 0.0590(4) Uani 1 1 d . . . . . H00C H 0.047290 0.731984 0.622048 0.071 Uiso 1 1 calc R U . . . C24 C 0.5339(2) 0.46967(16) 0.25967(16) 0.0619(5) Uani 1 1 d . . . . . H00D H 0.554647 0.400298 0.290634 0.074 Uiso 1 1 calc R U . . . C5 C -0.0595(2) 0.83656(15) 0.07839(14) 0.0524(4) Uani 1 1 d . . . . . C21 C 0.4708(2) 0.67659(16) 0.16749(15) 0.0572(4) Uani 1 1 d . . . . . C23 C 0.6211(2) 0.51353(17) 0.17869(17) 0.0634(5) Uani 1 1 d . . . . . C22 C 0.5872(2) 0.61626(17) 0.13343(16) 0.0625(5) Uani 1 1 d . . . . . H00H H 0.644153 0.646147 0.078265 0.075 Uiso 1 1 calc R U . . . C19 C -0.0349(2) 0.64204(19) 0.41308(17) 0.0690(5) Uani 1 1 d . . . . . H00A H -0.103516 0.689960 0.366408 0.103 Uiso 1 1 calc R U . . . H00E H -0.093643 0.607646 0.468535 0.103 Uiso 1 1 calc R U . . . H00F H -0.010420 0.583398 0.364982 0.103 Uiso 1 1 calc R U . . . C14 C 0.2813(3) 0.81760(16) 0.65092(15) 0.0621(5) Uani 1 1 d . . . . . C6 C -0.1613(2) 0.91020(18) 0.01817(16) 0.0619(5) Uani 1 1 d . . . . . H00K H -0.180401 0.976049 0.054102 0.074 Uiso 1 1 calc R U . . . C28 C 0.3206(3) 0.47103(17) 0.38066(18) 0.0684(5) Uani 1 1 d . . . . . H00G H 0.332287 0.522515 0.446164 0.103 Uiso 1 1 calc R U . . . H00I H 0.365031 0.402742 0.405263 0.103 Uiso 1 1 calc R U . . . H00J H 0.203996 0.452063 0.344471 0.103 Uiso 1 1 calc R U . . . C18 C 0.2900(3) 0.8614(2) 0.77225(17) 0.0828(7) Uani 1 1 d . . . . . H00L H 0.376316 0.830180 0.824076 0.124 Uiso 1 1 calc R U . . . H00M H 0.183983 0.838675 0.793036 0.124 Uiso 1 1 calc R U . . . H00N H 0.315348 0.943144 0.776942 0.124 Uiso 1 1 calc R U . . . C7 C -0.2320(3) 0.8821(2) -0.09528(17) 0.0714(5) Uani 1 1 d . . . . . H00O H -0.298056 0.930735 -0.137437 0.086 Uiso 1 1 calc R U . . . C9 C -0.1080(3) 0.7086(2) -0.09221(16) 0.0720(5) Uani 1 1 d . . . . . H00P H -0.091678 0.641774 -0.127918 0.086 Uiso 1 1 calc R U . . . C26 C 0.4498(3) 0.79027(19) 0.11599(19) 0.0758(6) Uani 1 1 d . . . . . H00Q H 0.349058 0.782114 0.057122 0.114 Uiso 1 1 calc R U . . . H00R H 0.544574 0.816488 0.083026 0.114 Uiso 1 1 calc R U . . . H00S H 0.442543 0.844635 0.175031 0.114 Uiso 1 1 calc R U . . . C4 C 0.0402(4) 0.9889(2) 0.3531(2) 0.0881(7) Uani 1 1 d . . . . . H00T H 0.038454 1.045748 0.407766 0.106 Uiso 1 1 calc R U . . . C17 C 0.5684(3) 0.8349(2) 0.4392(2) 0.0772(6) Uani 1 1 d . . . . . H00U H 0.606976 0.766966 0.416460 0.116 Uiso 1 1 calc R U . . . H00V H 0.654715 0.878210 0.496989 0.116 Uiso 1 1 calc R U . . . H00W H 0.542039 0.880112 0.373500 0.116 Uiso 1 1 calc R U . . . C27 C 0.7497(3) 0.4515(2) 0.1404(2) 0.0838(7) Uani 1 1 d . . . . . H00X H 0.789525 0.400768 0.198420 0.126 Uiso 1 1 calc R U . . . H00Y H 0.842148 0.505914 0.128951 0.126 Uiso 1 1 calc R U . . . H H 0.699425 0.408414 0.069538 0.126 Uiso 1 1 calc R U . . . C8 C -0.2071(3) 0.7822(2) -0.14930(17) 0.0790(6) Uani 1 1 d . . . . . H00Z H -0.259256 0.765049 -0.226127 0.095 Uiso 1 1 calc R U . . . B1 B 0.2546(2) 0.70058(16) 0.29325(16) 0.0498(4) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0624(7) 0.0694(8) 0.0461(6) -0.0042(5) 0.0087(5) 0.0136(6) C11 0.0513(8) 0.0523(9) 0.0463(8) 0.0037(6) 0.0088(6) 0.0116(7) C2 0.0509(9) 0.0612(10) 0.0464(8) 0.0017(7) 0.0121(7) 0.0067(7) C1 0.0536(9) 0.0612(10) 0.0438(8) -0.0020(7) 0.0118(7) 0.0065(7) C20 0.0499(8) 0.0546(9) 0.0473(8) 0.0008(7) 0.0105(7) 0.0053(7) C16 0.0545(9) 0.0593(9) 0.0473(8) 0.0050(7) 0.0115(7) 0.0120(7) C25 0.0551(9) 0.0548(9) 0.0522(9) -0.0010(7) 0.0089(7) 0.0049(7) C10 0.0489(9) 0.0707(11) 0.0466(8) 0.0032(7) 0.0097(7) 0.0062(8) C12 0.0521(9) 0.0557(9) 0.0545(9) 0.0004(7) 0.0070(7) 0.0120(7) C3 0.0694(11) 0.0659(11) 0.0520(9) 0.0016(8) 0.0096(8) 0.0160(9) C13 0.0616(10) 0.0609(10) 0.0542(9) -0.0045(8) -0.0014(8) 0.0139(8) C15 0.0641(10) 0.0685(11) 0.0488(9) 0.0049(8) 0.0164(8) 0.0182(9) C24 0.0626(10) 0.0549(10) 0.0671(11) -0.0032(8) 0.0107(9) 0.0103(8) C5 0.0455(8) 0.0632(10) 0.0482(8) 0.0058(7) 0.0116(6) 0.0041(7) C21 0.0562(9) 0.0622(10) 0.0546(9) 0.0021(7) 0.0168(7) 0.0061(8) C23 0.0536(10) 0.0666(11) 0.0688(11) -0.0143(9) 0.0133(8) 0.0066(8) C22 0.0560(10) 0.0720(12) 0.0614(10) -0.0034(9) 0.0212(8) 0.0033(8) C19 0.0573(10) 0.0881(14) 0.0592(10) 0.0024(9) 0.0167(8) -0.0033(9) C14 0.0741(12) 0.0649(11) 0.0481(9) -0.0011(8) 0.0053(8) 0.0247(9) C6 0.0536(9) 0.0729(11) 0.0589(10) 0.0097(8) 0.0107(8) 0.0094(8) C28 0.0795(13) 0.0612(11) 0.0687(11) 0.0122(9) 0.0238(10) 0.0110(9) C18 0.0951(16) 0.0993(16) 0.0534(11) -0.0143(10) 0.0101(10) 0.0229(13) C7 0.0578(11) 0.0916(15) 0.0611(11) 0.0148(10) 0.0037(8) 0.0101(10) C9 0.0681(12) 0.0937(15) 0.0505(10) -0.0097(9) 0.0053(8) 0.0117(10) C26 0.0824(14) 0.0769(13) 0.0774(13) 0.0210(10) 0.0364(11) 0.0121(11) C4 0.116(2) 0.0835(15) 0.0663(12) -0.0112(11) 0.0111(12) 0.0334(14) C17 0.0593(11) 0.0875(14) 0.0800(13) -0.0109(11) 0.0159(10) -0.0054(10) C27 0.0728(13) 0.0847(15) 0.0992(16) -0.0175(12) 0.0270(12) 0.0191(11) C8 0.0683(12) 0.1103(17) 0.0507(10) 0.0024(11) -0.0014(9) 0.0080(12) B1 0.0506(9) 0.0500(9) 0.0479(9) 0.0034(7) 0.0117(7) 0.0027(7) 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 C10 O1 C1 107.04(13) . . ? C16 C11 B1 121.32(15) . . ? C12 C11 C16 118.19(15) . . ? C12 C11 B1 120.46(15) . . ? C1 C2 C3 127.64(16) . . ? C1 C2 C5 107.40(15) . . ? C3 C2 C5 124.95(16) . . ? O1 C1 B1 117.52(14) . . ? C2 C1 O1 109.27(14) . . ? C2 C1 B1 132.55(15) . . ? C25 C20 C21 118.31(15) . . ? C25 C20 B1 121.12(14) . . ? C21 C20 B1 120.57(15) . . ? C11 C16 C19 121.98(15) . . ? C15 C16 C11 119.98(16) . . ? C15 C16 C19 118.03(16) . . ? C20 C25 C28 121.64(16) . . ? C24 C25 C20 120.16(16) . . ? C24 C25 C28 118.15(16) . . ? O1 C10 C5 110.76(14) . . ? O1 C10 C9 125.83(17) . . ? C9 C10 C5 123.40(18) . . ? C11 C12 C17 122.44(16) . . ? C13 C12 C11 119.68(16) . . ? C13 C12 C17 117.83(16) . . ? C4 C3 C2 175.4(2) . . ? C12 C13 H00B 118.9 . . ? C14 C13 C12 122.20(17) . . ? C14 C13 H00B 118.9 . . ? C16 C15 H00C 118.9 . . ? C14 C15 C16 122.12(17) . . ? C14 C15 H00C 118.9 . . ? C25 C24 H00D 119.2 . . ? C23 C24 C25 121.52(17) . . ? C23 C24 H00D 119.2 . . ? C10 C5 C2 105.48(15) . . ? C10 C5 C6 119.35(16) . . ? C6 C5 C2 135.16(17) . . ? C20 C21 C26 122.79(16) . . ? C22 C21 C20 119.61(17) . . ? C22 C21 C26 117.55(16) . . ? C24 C23 C27 121.3(2) . . ? C22 C23 C24 118.11(17) . . ? C22 C23 C27 120.6(2) . . ? C21 C22 H00H 118.9 . . ? C23 C22 C21 122.29(17) . . ? C23 C22 H00H 118.9 . . ? C16 C19 H00A 109.5 . . ? C16 C19 H00E 109.5 . . ? C16 C19 H00F 109.5 . . ? H00A C19 H00E 109.5 . . ? H00A C19 H00F 109.5 . . ? H00E C19 H00F 109.5 . . ? C13 C14 C18 120.75(19) . . ? C15 C14 C13 117.77(16) . . ? C15 C14 C18 121.48(19) . . ? C5 C6 H00K 121.1 . . ? C7 C6 C5 117.78(19) . . ? C7 C6 H00K 121.1 . . ? C25 C28 H00G 109.5 . . ? C25 C28 H00I 109.5 . . ? C25 C28 H00J 109.5 . . ? H00G C28 H00I 109.5 . . ? H00G C28 H00J 109.5 . . ? H00I C28 H00J 109.5 . . ? C14 C18 H00L 109.5 . . ? C14 C18 H00M 109.5 . . ? C14 C18 H00N 109.5 . . ? H00L C18 H00M 109.5 . . ? H00L C18 H00N 109.5 . . ? H00M C18 H00N 109.5 . . ? C6 C7 H00O 119.2 . . ? C6 C7 C8 121.54(19) . . ? C8 C7 H00O 119.2 . . ? C10 C9 H00P 122.0 . . ? C8 C9 C10 116.1(2) . . ? C8 C9 H00P 122.0 . . ? C21 C26 H00Q 109.5 . . ? C21 C26 H00R 109.5 . . ? C21 C26 H00S 109.5 . . ? H00Q C26 H00R 109.5 . . ? H00Q C26 H00S 109.5 . . ? H00R C26 H00S 109.5 . . ? C3 C4 H00T 180.0 . . ? C12 C17 H00U 109.5 . . ? C12 C17 H00V 109.5 . . ? C12 C17 H00W 109.5 . . ? H00U C17 H00V 109.5 . . ? H00U C17 H00W 109.5 . . ? H00V C17 H00W 109.5 . . ? C23 C27 H00X 109.5 . . ? C23 C27 H00Y 109.5 . . ? C23 C27 H 109.5 . . ? H00X C27 H00Y 109.5 . . ? H00X C27 H 109.5 . . ? H00Y C27 H 109.5 . . ? C7 C8 H00Z 119.1 . . ? C9 C8 C7 121.81(19) . . ? C9 C8 H00Z 119.1 . . ? C11 B1 C20 124.44(14) . . ? C1 B1 C11 117.87(15) . . ? C1 B1 C20 117.56(14) . . ? 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 1.3961(19) . ? O1 C10 1.367(2) . ? C11 C16 1.411(2) . ? C11 C12 1.410(2) . ? C11 B1 1.570(2) . ? C2 C1 1.372(2) . ? C2 C3 1.418(2) . ? C2 C5 1.441(2) . ? C1 B1 1.548(3) . ? C20 C25 1.405(2) . ? C20 C21 1.410(2) . ? C20 B1 1.572(2) . ? C16 C15 1.388(2) . ? C16 C19 1.510(3) . ? C25 C24 1.397(2) . ? C25 C28 1.507(3) . ? C10 C5 1.386(3) . ? C10 C9 1.384(2) . ? C12 C13 1.393(2) . ? C12 C17 1.509(3) . ? C3 C4 1.175(3) . ? C13 H00B 0.9300 . ? C13 C14 1.384(3) . ? C15 H00C 0.9300 . ? C15 C14 1.383(3) . ? C24 H00D 0.9300 . ? C24 C23 1.383(3) . ? C5 C6 1.399(2) . ? C21 C22 1.391(3) . ? C21 C26 1.507(3) . ? C23 C22 1.381(3) . ? C23 C27 1.507(3) . ? C22 H00H 0.9300 . ? C19 H00A 0.9600 . ? C19 H00E 0.9600 . ? C19 H00F 0.9600 . ? C14 C18 1.507(2) . ? C6 H00K 0.9300 . ? C6 C7 1.368(3) . ? C28 H00G 0.9600 . ? C28 H00I 0.9600 . ? C28 H00J 0.9600 . ? C18 H00L 0.9600 . ? C18 H00M 0.9600 . ? C18 H00N 0.9600 . ? C7 H00O 0.9300 . ? C7 C8 1.396(3) . ? C9 H00P 0.9300 . ? C9 C8 1.371(3) . ? C26 H00Q 0.9600 . ? C26 H00R 0.9600 . ? C26 H00S 0.9600 . ? C4 H00T 0.9300 . ? C17 H00U 0.9600 . ? C17 H00V 0.9600 . ? C17 H00W 0.9600 . ? C27 H00X 0.9600 . ? C27 H00Y 0.9600 . ? C27 H 0.9600 . ? C8 H00Z 0.9300 . ? 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 C11 -161.14(14) . . . . ? O1 C1 B1 C20 22.9(2) . . . . ? O1 C10 C5 C2 -1.67(19) . . . . ? O1 C10 C5 C6 178.35(14) . . . . ? O1 C10 C9 C8 -178.41(18) . . . . ? C11 C16 C15 C14 1.9(3) . . . . ? C11 C12 C13 C14 2.2(3) . . . . ? C2 C1 B1 C11 29.3(3) . . . . ? C2 C1 B1 C20 -146.68(18) . . . . ? C2 C5 C6 C7 -179.76(18) . . . . ? C1 O1 C10 C5 0.80(19) . . . . ? C1 O1 C10 C9 -178.85(18) . . . . ? C1 C2 C5 C10 1.91(19) . . . . ? C1 C2 C5 C6 -178.12(19) . . . . ? C20 C25 C24 C23 -0.3(3) . . . . ? C20 C21 C22 C23 -0.2(3) . . . . ? C16 C11 C12 C13 -2.2(2) . . . . ? C16 C11 C12 C17 -179.82(17) . . . . ? C16 C11 B1 C1 56.4(2) . . . . ? C16 C11 B1 C20 -127.89(18) . . . . ? C16 C15 C14 C13 -2.0(3) . . . . ? C16 C15 C14 C18 178.27(18) . . . . ? C25 C20 C21 C22 -0.6(3) . . . . ? C25 C20 C21 C26 -178.02(18) . . . . ? C25 C20 B1 C11 56.1(2) . . . . ? C25 C20 B1 C1 -128.23(17) . . . . ? C25 C24 C23 C22 -0.5(3) . . . . ? C25 C24 C23 C27 179.54(18) . . . . ? C10 O1 C1 C2 0.47(18) . . . . ? C10 O1 C1 B1 -171.38(14) . . . . ? C10 C5 C6 C7 0.2(3) . . . . ? C10 C9 C8 C7 -0.3(3) . . . . ? C12 C11 C16 C15 0.2(2) . . . . ? C12 C11 C16 C19 -178.36(16) . . . . ? C12 C11 B1 C1 -121.32(17) . . . . ? C12 C11 B1 C20 54.4(2) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? C12 C13 C14 C18 179.69(18) . . . . ? C3 C2 C1 O1 179.39(17) . . . . ? C3 C2 C1 B1 -10.4(3) . . . . ? C3 C2 C5 C10 -178.93(17) . . . . ? C3 C2 C5 C6 1.0(3) . . . . ? C24 C23 C22 C21 0.7(3) . . . . ? C5 C2 C1 O1 -1.49(19) . . . . ? C5 C2 C1 B1 168.69(17) . . . . ? C5 C10 C9 C8 2.0(3) . . . . ? C5 C6 C7 C8 1.4(3) . . . . ? C21 C20 C25 C24 0.9(2) . . . . ? C21 C20 C25 C28 -176.76(17) . . . . ? C21 C20 B1 C11 -122.77(18) . . . . ? C21 C20 B1 C1 52.9(2) . . . . ? C19 C16 C15 C14 -179.47(18) . . . . ? C6 C7 C8 C9 -1.4(3) . . . . ? C28 C25 C24 C23 177.36(17) . . . . ? C9 C10 C5 C2 177.98(17) . . . . ? C9 C10 C5 C6 -2.0(3) . . . . ? C26 C21 C22 C23 177.36(18) . . . . ? C17 C12 C13 C14 179.90(18) . . . . ? C27 C23 C22 C21 -179.28(18) . . . . ? B1 C11 C16 C15 -177.53(15) . . . . ? B1 C11 C16 C19 3.9(3) . . . . ? B1 C11 C12 C13 175.61(15) . . . . ? B1 C11 C12 C17 -2.0(3) . . . . ? B1 C20 C25 C24 -178.00(15) . . . . ? B1 C20 C25 C28 4.4(2) . . . . ? B1 C20 C21 C22 178.26(16) . . . . ? B1 C20 C21 C26 0.8(3) . . . . ?