#------------------------------------------------------------------------------ #$Date: 2021-11-09 01:14:31 +0200 (Tue, 09 Nov 2021) $ #$Revision: 270530 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/51/1565137.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_1565137 loop_ _publ_author_name 'Zhu, Zhaoyang' 'Zhang, Xue' 'Guo, Xing' 'Wu, Qinghua' 'Li, Zhongxin' 'Yu, Changjiang' 'Hao, Erhong' 'Jiao, Lijuan' 'Zhao, Jianzhang' _publ_section_title ; Orthogonally aligned cyclic BODIPY arrays with long-lived triplet excited states as efficient heavy-atom-free photosensitizers ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D1SC04893G _journal_year 2021 _chemical_formula_moiety 'C50 H44 B2 Cl2 N4 O4' _chemical_formula_sum 'C50 H44 B2 Cl2 N4 O4' _chemical_formula_weight 857.41 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-04-07 _audit_creation_method ; Olex2 1.2-beta (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-05-13 deposited with the CCDC. 2021-10-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 114.175(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 24.9180(13) _cell_length_b 13.8086(6) _cell_length_c 14.4975(5) _cell_measurement_reflns_used 9511 _cell_measurement_temperature 300(2) _cell_measurement_theta_max 27.28 _cell_measurement_theta_min 2.95 _cell_volume 4550.9(4) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 300.02 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.995 _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 0.0465 _diffrn_reflns_av_unetI/netI 0.0170 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 93718 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.537 _diffrn_reflns_theta_min 2.950 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.7127 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0682 before and 0.0511 after correction. The Ratio of minimum to maximum transmission is 0.9559. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear orangish orange' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier orangish _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.251 _exptl_crystal_description needle _exptl_crystal_F_000 1792 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _refine_diff_density_max 0.259 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.040 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 284 _refine_ls_number_reflns 5232 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0477 _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^)+(0.0584P)^2^+3.7714P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1181 _refine_ls_wR_factor_ref 0.1307 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4069 _reflns_number_total 5232 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc04893g2.cif _cod_data_source_block a _cod_database_code 1565137 _shelx_shelxl_version_number 2014/7 _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. ; _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: C10(H10), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C28(H28) 2.b Idealised Me refined as rotating group: C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C30(H30A,H30B, H30C) ; _shelx_res_file ; a.res created by SHELXL-2014/7 TITL A in C2/c #15 REM reset to C2/c #15 CELL 0.71073 24.91802 13.8086 14.4975 90 114.1748 90 ZERR 4 0.00134 0.0006 0.0005 0 0.0026 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H B Cl N O UNIT 200 176 8 8 16 16 L.S. 10 PLAN 20 TEMP 26.87 BOND fmap 2 53 acta REM REM REM WGHT 0.058400 3.771400 FVAR 0.09710 N0AA 5 0.112429 0.320994 -0.049371 11.00000 0.03677 0.03372 = 0.03456 0.00482 0.01278 0.00125 N3 5 0.063921 0.332376 -0.235714 11.00000 0.03202 0.03121 = 0.03443 0.00069 0.01006 -0.00294 C4 1 0.146660 0.400367 -0.050456 11.00000 0.03592 0.03198 = 0.03746 -0.00006 0.01261 -0.00115 C5 1 0.141841 0.443695 -0.141535 11.00000 0.03421 0.03078 = 0.03719 0.00033 0.01221 -0.00044 C6 1 0.101474 0.409505 -0.232201 11.00000 0.03640 0.03215 = 0.03752 0.00220 0.01230 -0.00429 C7 1 0.179854 0.528929 -0.135657 11.00000 0.04275 0.03797 = 0.03149 -0.00281 0.01196 -0.00976 C8 1 0.027567 0.319180 -0.332794 11.00000 0.03236 0.03513 = 0.03759 -0.00465 0.01205 -0.00190 C9 1 0.128328 0.300041 0.049334 11.00000 0.04319 0.04247 = 0.03916 0.00904 0.01729 0.00584 C10 1 0.171286 0.362177 0.111675 11.00000 0.05352 0.05573 = 0.03256 0.00043 0.01218 0.00139 AFIX 43 H10 2 0.188902 0.361336 0.181966 11.00000 -1.20000 AFIX 0 C11 1 0.239142 0.515115 -0.115616 11.00000 0.04339 0.06449 = 0.03894 -0.00424 0.01436 -0.01131 C12 1 0.095563 0.160669 -0.157384 11.00000 0.03337 0.03403 = 0.04474 0.00238 0.01124 0.00139 B13 3 0.070040 0.263996 -0.145468 11.00000 0.03141 0.03179 = 0.03897 0.00450 0.01249 -0.00048 C14 1 0.140427 0.153645 -0.190005 11.00000 0.05248 0.04591 = 0.06231 0.00567 0.02978 0.00453 AFIX 43 H14 2 0.156632 0.209980 -0.202894 11.00000 -1.20000 AFIX 0 C15 1 0.086244 0.440837 -0.332901 11.00000 0.05323 0.04686 = 0.03967 0.00418 0.01628 -0.01302 AFIX 43 H15 2 0.104310 0.490537 -0.352919 11.00000 -1.20000 AFIX 0 C16 1 0.040641 0.385606 -0.395115 11.00000 0.05140 0.05440 = 0.03253 0.00097 0.01161 -0.01092 AFIX 43 H16 2 0.021681 0.390497 -0.465113 11.00000 -1.20000 AFIX 0 C17 1 0.182772 0.425607 0.048784 11.00000 0.04712 0.04603 = 0.03718 -0.00429 0.01073 -0.00466 AFIX 43 H17 2 0.209770 0.476195 0.068906 11.00000 -1.20000 AFIX 0 C18 1 0.156367 0.622090 -0.145053 11.00000 0.06707 0.03714 = 0.04196 -0.00285 0.01980 -0.00685 C19 1 0.273523 0.597640 -0.107137 11.00000 0.05332 0.10321 = 0.04187 -0.01044 0.01844 -0.03661 AFIX 43 H19 2 0.313111 0.589624 -0.093535 11.00000 -1.20000 AFIX 0 C20 1 0.073502 0.075252 -0.135710 11.00000 0.04544 0.03513 = 0.10233 0.00607 0.03578 0.00286 AFIX 43 H20 2 0.043593 0.077730 -0.113058 11.00000 -1.20000 AFIX 0 C21 1 0.193296 0.700471 -0.135912 11.00000 0.10836 0.04037 = 0.04794 -0.00561 0.03139 -0.02159 AFIX 43 H21 2 0.177893 0.762683 -0.142215 11.00000 -1.20000 AFIX 0 C22 1 0.161732 0.064904 -0.203890 11.00000 0.06243 0.06413 = 0.07537 0.00206 0.03736 0.01692 AFIX 43 H22 2 0.191556 0.062152 -0.226729 11.00000 -1.20000 AFIX 0 C23 1 0.251193 0.689894 -0.118079 11.00000 0.10077 0.06888 = 0.03840 -0.01346 0.02863 -0.04835 C24 1 0.095857 -0.013801 -0.147676 11.00000 0.06388 0.03274 = 0.13932 0.00551 0.04387 0.00229 C25 1 0.093351 0.639373 -0.162972 11.00000 0.08145 0.05173 = 0.09827 0.00060 0.03334 0.01651 AFIX 137 H25A 2 0.067990 0.614255 -0.228057 11.00000 -1.50000 H25B 2 0.086666 0.707642 -0.160844 11.00000 -1.50000 H25C 2 0.085119 0.607268 -0.111467 11.00000 -1.50000 AFIX 0 O26 6 0.077909 -0.100783 -0.125662 11.00000 0.11909 0.03382 = 0.30309 0.01713 0.12435 0.00258 C27 1 0.265809 0.415962 -0.103300 11.00000 0.04884 0.08921 = 0.08315 -0.00205 0.02694 0.01006 AFIX 137 H27A 2 0.281547 0.397809 -0.033257 11.00000 -1.50000 H27B 2 0.296788 0.416378 -0.126496 11.00000 -1.50000 H27C 2 0.236156 0.370252 -0.142267 11.00000 -1.50000 AFIX 0 C28 1 0.139335 -0.017893 -0.184363 11.00000 0.07136 0.04542 = 0.11480 -0.00726 0.04161 0.01587 AFIX 43 H28 2 0.153009 -0.077521 -0.195469 11.00000 -1.20000 AFIX 0 C29 1 0.289452 0.776683 -0.113206 11.00000 0.16885 0.11552 = 0.07323 -0.02788 0.05832 -0.10198 AFIX 137 H29A 2 0.330072 0.759762 -0.076348 11.00000 -1.50000 H29B 2 0.279532 0.829182 -0.079661 11.00000 -1.50000 H29C 2 0.282998 0.796102 -0.180521 11.00000 -1.50000 AFIX 0 C30 1 0.036180 -0.099674 -0.082691 11.00000 0.14882 0.05765 = 0.41503 0.06758 0.18317 0.01021 AFIX 137 H30A 2 -0.001403 -0.080176 -0.132956 11.00000 -1.50000 H30B 2 0.048558 -0.054787 -0.027285 11.00000 -1.50000 H30C 2 0.033060 -0.163304 -0.058662 11.00000 -1.50000 AFIX 0 CL1 4 0.096395 0.208577 0.088362 11.00000 0.06718 0.06656 = 0.05360 0.02010 0.02558 -0.00695 O2 6 -0.012532 0.250727 -0.360205 11.00000 0.03110 0.03589 = 0.04874 -0.01185 0.01504 -0.00465 HKLF 4 REM A in C2/c #15 REM R1 = 0.0477 for 4069 Fo > 4sig(Fo) and 0.0658 for all 5232 data REM 284 parameters refined using 0 restraints END WGHT 0.0585 3.7722 REM Highest difference peak 0.259, deepest hole -0.320, 1-sigma level 0.040 Q1 1 0.0785 0.2058 -0.1536 11.00000 0.05 0.26 Q2 1 0.0828 0.1645 0.0435 11.00000 0.05 0.25 Q3 1 0.2117 0.5192 0.1012 11.00000 0.05 0.22 Q4 1 0.1602 0.4838 -0.1430 11.00000 0.05 0.21 Q5 1 0.1222 0.3659 -0.0592 11.00000 0.05 0.19 Q6 1 0.0608 0.5675 -0.1719 11.00000 0.05 0.18 Q7 1 0.1447 0.4224 -0.0960 11.00000 0.05 0.18 Q8 1 0.0654 0.3057 -0.1987 11.00000 0.05 0.17 Q9 1 0.2414 0.3595 -0.0865 11.00000 0.05 0.17 Q10 1 0.3176 0.7749 -0.1472 11.00000 0.05 0.16 Q11 1 0.1634 0.4270 -0.0071 11.00000 0.05 0.16 Q12 1 0.1411 -0.0188 -0.1245 11.00000 0.05 0.16 Q13 1 0.3177 0.7978 -0.0480 11.00000 0.05 0.16 Q14 1 0.0763 0.2639 0.0734 11.00000 0.05 0.16 Q15 1 0.0803 0.1230 -0.1546 11.00000 0.05 0.16 Q16 1 0.0989 0.2956 -0.0884 11.00000 0.05 0.16 Q17 1 0.3156 0.4142 -0.0546 11.00000 0.05 0.15 Q18 1 0.1609 0.5769 -0.1539 11.00000 0.05 0.15 Q19 1 0.0369 0.3369 -0.3704 11.00000 0.05 0.15 Q20 1 0.2042 0.5183 -0.1406 11.00000 0.05 0.14 ; _shelx_res_checksum 87507 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 N0AA N 0.11243(6) 0.32099(9) -0.04937(9) 0.0356(3) Uani 1 1 d . . . . . N3 N 0.06392(5) 0.33238(9) -0.23571(9) 0.0337(3) Uani 1 1 d . . . . . C4 C 0.14666(7) 0.40037(11) -0.05046(12) 0.0359(3) Uani 1 1 d . . . . . C5 C 0.14184(7) 0.44369(11) -0.14153(12) 0.0348(3) Uani 1 1 d . . . . . C6 C 0.10147(7) 0.40951(11) -0.23220(12) 0.0363(3) Uani 1 1 d . . . . . C7 C 0.17985(7) 0.52893(12) -0.13566(11) 0.0385(4) Uani 1 1 d . . . . . C8 C 0.02757(7) 0.31918(11) -0.33279(12) 0.0358(3) Uani 1 1 d . . . . . C9 C 0.12833(8) 0.30004(12) 0.04933(12) 0.0415(4) Uani 1 1 d . . . . . C10 C 0.17129(8) 0.36218(14) 0.11167(13) 0.0491(4) Uani 1 1 d . . . . . H10 H 0.1889 0.3613 0.1820 0.059 Uiso 1 1 calc R . . . . C11 C 0.23914(8) 0.51512(15) -0.11562(13) 0.0498(4) Uani 1 1 d . . . . . C12 C 0.09556(7) 0.16067(12) -0.15738(12) 0.0389(4) Uani 1 1 d . . . . . B13 B 0.07004(8) 0.26400(13) -0.14547(13) 0.0347(4) Uani 1 1 d . . . . . C14 C 0.14043(9) 0.15365(14) -0.19001(15) 0.0515(4) Uani 1 1 d . . . . . H14 H 0.1566 0.2100 -0.2029 0.062 Uiso 1 1 calc R . . . . C15 C 0.08624(8) 0.44084(13) -0.33290(13) 0.0475(4) Uani 1 1 d . . . . . H15 H 0.1043 0.4905 -0.3529 0.057 Uiso 1 1 calc R . . . . C16 C 0.04064(8) 0.38561(14) -0.39512(13) 0.0479(4) Uani 1 1 d . . . . . H16 H 0.0217 0.3905 -0.4651 0.058 Uiso 1 1 calc R . . . . C17 C 0.18277(8) 0.42561(13) 0.04878(13) 0.0456(4) Uani 1 1 d . . . . . H17 H 0.2098 0.4762 0.0689 0.055 Uiso 1 1 calc R . . . . C18 C 0.15637(9) 0.62209(13) -0.14505(13) 0.0496(4) Uani 1 1 d . . . . . C19 C 0.27352(10) 0.5976(2) -0.10714(15) 0.0665(7) Uani 1 1 d . . . . . H19 H 0.3131 0.5896 -0.0935 0.080 Uiso 1 1 calc R . . . . C20 C 0.07350(9) 0.07525(13) -0.13571(19) 0.0592(5) Uani 1 1 d . . . . . H20 H 0.0436 0.0777 -0.1131 0.071 Uiso 1 1 calc R . . . . C21 C 0.19330(13) 0.70047(15) -0.13591(15) 0.0658(6) Uani 1 1 d . . . . . H21 H 0.1779 0.7627 -0.1422 0.079 Uiso 1 1 calc R . . . . C22 C 0.16173(10) 0.06490(17) -0.20389(18) 0.0643(6) Uani 1 1 d . . . . . H22 H 0.1916 0.0622 -0.2267 0.077 Uiso 1 1 calc R . . . . C23 C 0.25119(13) 0.68989(18) -0.11808(15) 0.0693(7) Uani 1 1 d . . . . . C24 C 0.09586(10) -0.01380(15) -0.1477(2) 0.0779(8) Uani 1 1 d . . . . . C25 C 0.09335(11) 0.63937(17) -0.1630(2) 0.0783(7) Uani 1 1 d . . . . . H25A H 0.0680 0.6143 -0.2281 0.117 Uiso 1 1 calc GR . . . . H25B H 0.0867 0.7076 -0.1608 0.117 Uiso 1 1 calc GR . . . . H25C H 0.0851 0.6073 -0.1115 0.117 Uiso 1 1 calc GR . . . . O26 O 0.07791(11) -0.10078(12) -0.1257(3) 0.1396(12) Uani 1 1 d . . . . . C27 C 0.26581(10) 0.41596(19) -0.1033(2) 0.0738(7) Uani 1 1 d . . . . . H27A H 0.2815 0.3978 -0.0333 0.111 Uiso 1 1 calc GR . . . . H27B H 0.2968 0.4164 -0.1265 0.111 Uiso 1 1 calc GR . . . . H27C H 0.2362 0.3703 -0.1423 0.111 Uiso 1 1 calc GR . . . . C28 C 0.13934(11) -0.01789(16) -0.1844(2) 0.0760(7) Uani 1 1 d . . . . . H28 H 0.1530 -0.0775 -0.1955 0.091 Uiso 1 1 calc R . . . . C29 C 0.28945(17) 0.7767(2) -0.1132(2) 0.1163(14) Uani 1 1 d . . . . . H29A H 0.3301 0.7598 -0.0763 0.174 Uiso 1 1 calc GR . . . . H29B H 0.2795 0.8292 -0.0797 0.174 Uiso 1 1 calc GR . . . . H29C H 0.2830 0.7961 -0.1805 0.174 Uiso 1 1 calc GR . . . . C30 C 0.0362(2) -0.0997(2) -0.0827(5) 0.185(3) Uani 1 1 d . . . . . H30A H -0.0014 -0.0802 -0.1330 0.277 Uiso 1 1 calc GR . . . . H30B H 0.0486 -0.0548 -0.0273 0.277 Uiso 1 1 calc GR . . . . H30C H 0.0331 -0.1633 -0.0587 0.277 Uiso 1 1 calc GR . . . . Cl1 Cl 0.09639(2) 0.20858(4) 0.08836(4) 0.06217(17) Uani 1 1 d . . . . . O2 O -0.01253(5) 0.25073(8) -0.36020(9) 0.0390(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 N0AA 0.0368(7) 0.0337(7) 0.0346(7) 0.0048(5) 0.0128(5) 0.0013(5) N3 0.0320(6) 0.0312(6) 0.0344(6) 0.0007(5) 0.0101(5) -0.0029(5) C4 0.0359(8) 0.0320(8) 0.0375(8) -0.0001(6) 0.0126(6) -0.0012(6) C5 0.0342(8) 0.0308(8) 0.0372(8) 0.0003(6) 0.0122(6) -0.0004(6) C6 0.0364(8) 0.0322(8) 0.0375(8) 0.0022(6) 0.0123(6) -0.0043(6) C7 0.0427(9) 0.0380(8) 0.0315(7) -0.0028(6) 0.0120(7) -0.0098(7) C8 0.0324(8) 0.0351(8) 0.0376(8) -0.0047(6) 0.0120(6) -0.0019(6) C9 0.0432(9) 0.0425(9) 0.0392(8) 0.0090(7) 0.0173(7) 0.0058(7) C10 0.0535(10) 0.0557(11) 0.0326(8) 0.0004(7) 0.0122(7) 0.0014(9) C11 0.0434(9) 0.0645(12) 0.0389(9) -0.0042(8) 0.0144(8) -0.0113(8) C12 0.0334(8) 0.0340(8) 0.0447(9) 0.0024(7) 0.0112(7) 0.0014(6) B13 0.0314(8) 0.0318(9) 0.0390(9) 0.0045(7) 0.0125(7) -0.0005(7) C14 0.0525(10) 0.0459(10) 0.0623(11) 0.0057(9) 0.0298(9) 0.0045(8) C15 0.0532(10) 0.0469(10) 0.0397(9) 0.0042(7) 0.0163(8) -0.0130(8) C16 0.0514(10) 0.0544(11) 0.0325(8) 0.0010(7) 0.0116(7) -0.0109(8) C17 0.0471(9) 0.0460(10) 0.0372(8) -0.0043(7) 0.0107(7) -0.0047(8) C18 0.0671(12) 0.0371(9) 0.0420(9) -0.0029(7) 0.0198(9) -0.0069(8) C19 0.0533(11) 0.1032(19) 0.0419(10) -0.0104(11) 0.0184(9) -0.0366(12) C20 0.0454(10) 0.0351(9) 0.1023(17) 0.0061(10) 0.0358(11) 0.0029(8) C21 0.1084(19) 0.0404(10) 0.0479(11) -0.0056(8) 0.0314(12) -0.0216(11) C22 0.0624(13) 0.0641(13) 0.0754(14) 0.0021(11) 0.0374(11) 0.0169(11) C23 0.1008(19) 0.0689(15) 0.0384(10) -0.0135(9) 0.0286(11) -0.0483(14) C24 0.0639(14) 0.0327(10) 0.139(2) 0.0055(12) 0.0439(15) 0.0023(9) C25 0.0815(17) 0.0517(13) 0.0983(19) 0.0006(12) 0.0333(15) 0.0165(12) O26 0.1191(18) 0.0338(9) 0.303(4) 0.0171(14) 0.124(2) 0.0026(10) C27 0.0488(12) 0.0892(18) 0.0831(16) -0.0021(13) 0.0269(11) 0.0101(12) C28 0.0714(15) 0.0454(12) 0.115(2) -0.0073(12) 0.0416(15) 0.0159(11) C29 0.169(3) 0.116(2) 0.0732(17) -0.0279(16) 0.058(2) -0.102(2) C30 0.149(3) 0.0577(18) 0.415(9) 0.068(3) 0.183(5) 0.010(2) Cl1 0.0672(3) 0.0666(3) 0.0536(3) 0.0201(2) 0.0256(2) -0.0070(2) O2 0.0311(5) 0.0359(6) 0.0487(6) -0.0119(5) 0.0150(5) -0.0047(4) 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 C4 N0AA B13 125.19(12) . . ? C9 N0AA C4 105.38(13) . . ? C9 N0AA B13 129.12(13) . . ? C6 N3 B13 126.16(12) . . ? C8 N3 C6 107.18(12) . . ? C8 N3 B13 126.00(13) . . ? N0AA C4 C5 121.81(14) . . ? N0AA C4 C17 108.95(14) . . ? C17 C4 C5 129.24(15) . . ? C4 C5 C7 118.24(13) . . ? C6 C5 C4 119.98(14) . . ? C6 C5 C7 121.74(14) . . ? N3 C6 C15 107.50(13) . . ? C5 C6 N3 120.81(14) . . ? C5 C6 C15 131.63(15) . . ? C11 C7 C5 119.80(16) . . ? C18 C7 C5 119.37(15) . . ? C18 C7 C11 120.75(16) . . ? N3 C8 C16 110.45(14) . . ? O2 C8 N3 121.32(14) . . ? O2 C8 C16 128.21(14) . . ? N0AA C9 C10 111.89(15) . . ? N0AA C9 Cl1 122.35(13) . . ? C10 C9 Cl1 125.74(13) . . ? C17 C10 C9 106.12(15) . . ? C7 C11 C19 117.6(2) . . ? C7 C11 C27 121.90(17) . . ? C19 C11 C27 120.46(19) . . ? C14 C12 B13 120.78(15) . . ? C14 C12 C20 117.85(16) . . ? C20 C12 B13 121.37(15) . . ? N0AA B13 C12 112.93(13) . . ? N3 B13 N0AA 103.78(12) . . ? N3 B13 C12 110.71(13) . . ? O2 B13 N0AA 109.10(13) 2_554 . ? O2 B13 N3 110.80(12) 2_554 . ? O2 B13 C12 109.41(13) 2_554 . ? C22 C14 C12 121.59(18) . . ? C16 C15 C6 108.10(15) . . ? C15 C16 C8 106.76(15) . . ? C10 C17 C4 107.66(16) . . ? C7 C18 C25 122.00(17) . . ? C21 C18 C7 118.2(2) . . ? C21 C18 C25 119.8(2) . . ? C23 C19 C11 122.7(2) . . ? C24 C20 C12 120.43(19) . . ? C23 C21 C18 122.8(2) . . ? C28 C22 C14 120.2(2) . . ? C19 C23 C29 120.7(3) . . ? C21 C23 C19 117.90(19) . . ? C21 C23 C29 121.3(3) . . ? O26 C24 C20 124.3(2) . . ? O26 C24 C28 115.8(2) . . ? C28 C24 C20 119.9(2) . . ? C24 O26 C30 117.7(2) . . ? C22 C28 C24 119.9(2) . . ? C8 O2 B13 121.88(12) . 2_554 ? 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 N0AA C4 1.393(2) . ? N0AA C9 1.351(2) . ? N0AA B13 1.572(2) . ? N3 C6 1.4048(19) . ? N3 C8 1.3381(19) . ? N3 B13 1.569(2) . ? C4 C5 1.409(2) . ? C4 C17 1.393(2) . ? C5 C6 1.371(2) . ? C5 C7 1.491(2) . ? C6 C15 1.417(2) . ? C7 C11 1.397(3) . ? C7 C18 1.397(3) . ? C8 C16 1.416(2) . ? C8 O2 1.3132(18) . ? C9 C10 1.381(3) . ? C9 Cl1 1.7080(17) . ? C10 C17 1.376(3) . ? C11 C19 1.400(3) . ? C11 C27 1.500(3) . ? C12 B13 1.600(2) . ? C12 C14 1.384(2) . ? C12 C20 1.391(2) . ? B13 O2 1.480(2) 2_554 ? C14 C22 1.383(3) . ? C15 C16 1.359(2) . ? C18 C21 1.391(3) . ? C18 C25 1.502(3) . ? C19 C23 1.373(4) . ? C20 C24 1.390(3) . ? C21 C23 1.365(4) . ? C22 C28 1.352(3) . ? C23 C29 1.515(3) . ? C24 O26 1.364(3) . ? C24 C28 1.390(3) . ? O26 C30 1.414(4) . ? O2 B13 1.480(2) 2_554 ?