#------------------------------------------------------------------------------ #$Date: 2025-02-05 01:11:57 +0200 (Wed, 05 Feb 2025) $ #$Revision: 297591 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573847.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_1573847 loop_ _publ_author_name 'Procter, Richard James' 'Alamillo-Ferrer, Carla' 'Shabbir, Usman' 'Britton, Phyllida' 'Bucar, Dejan-Kresimir' 'Dumon, Alexandre Samuel' 'Rzepa, Henry S.' 'Bures, Jordi' 'Whiting, Andrew' 'Sheppard, Tom' _publ_section_title ; Borate-Catalysed Direct Amidation Reactions of Coordinating Substrates ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC07744J _journal_year 2025 _chemical_formula_moiety 'C23 H21 B3 N2 O3' _chemical_formula_sum 'C23 H21 B3 N2 O3' _chemical_formula_weight 405.85 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2019/3 _audit_update_record ; 2024-10-16 deposited with the CCDC. 2025-02-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 6.81856(4) _cell_length_b 18.79523(11) _cell_length_c 32.85532(19) _cell_measurement_reflns_used 63787 _cell_measurement_temperature 150.0(1) _cell_measurement_theta_max 77.8260 _cell_measurement_theta_min 4.6840 _cell_volume 4210.62(4) _computing_cell_refinement 'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.0(1) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_type 'HyPix-Arc 100' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, HyPix-Arc 100' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_unetI/netI 0.0114 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_number 94888 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 66.590 _diffrn_reflns_theta_max 66.590 _diffrn_reflns_theta_min 4.705 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.657 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_correction_T_min 0.883 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.280 _exptl_crystal_description prism _exptl_crystal_F_000 1696 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.165 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.033 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 286 _refine_ls_number_reflns 3713 _refine_ls_number_restraints 5 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0306 _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^)+(0.0443P)^2^+0.9773P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0804 _refine_ls_wR_factor_ref 0.0824 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3408 _reflns_number_total 3713 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc07744j2.cif _cod_data_source_block 1 _cod_database_code 1573847 _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_res_file ; TITL faces-xstr1656_filtered_a.res in Pbca faces-xstr1656_filtered.res created by SHELXL-2019/3 at 13:50:24 on 16-Oct-2024 REM Old TITL faces-xstr1656_filtered in Pbca REM SHELXT solution in Pbca: R1 0.115, Rweak 0.004, Alpha 0.013 REM 0.548 for 614 systematic absences, Orientation as input REM Formula found by SHELXT: C25 B N2 O3 CELL 1.54184 6.818557 18.795234 32.855321 90 90 90 ZERR 8 0.000041 0.000105 0.000185 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H B N O UNIT 184 168 24 16 24 DFIX 0.89 N2 H1N DFIX 0.89 N2 H2N DANG 1.5 H1N H2N! 1,3 dist H..H DANG 2 C1 H1N C1 H2N! L.S. 14 0 0 SHEL 100 0.84 PLAN 21 SIZE 0.04 0.12 0.23 TEMP -123 CONF BOND list 4 fmap 2 53 MORE -1 ACTA REM REM REM WGHT 0.044300 0.977300 FVAR 0.35543 N1 4 0.180647 0.556561 0.589791 11.00000 0.02388 0.03295 = 0.02964 0.00452 0.00081 0.00194 C1 1 0.006907 0.565413 0.570232 11.00000 0.02370 0.03680 = 0.03544 0.00440 0.00034 0.00183 B1 3 0.334389 0.621958 0.595173 11.00000 0.02408 0.03154 = 0.03197 0.00141 -0.00158 0.00269 O2 5 0.474945 0.698974 0.663109 11.00000 0.03007 0.03632 = 0.04007 -0.00317 -0.00390 0.00247 N2 4 -0.047511 0.631086 0.559062 11.00000 0.02705 0.03790 = 0.05717 0.00843 -0.01115 0.00178 REM R-NH2 (non planar) FIX H2N 2 -0.165403 0.637160 0.548194 11.00000 -1.50000 H1N 2 0.010972 0.668032 0.571377 11.00000 -1.50000 C2 1 -0.109339 0.505680 0.560734 11.00000 0.02770 0.04412 = 0.04588 0.00093 -0.00439 -0.00200 AFIX 43 H2 2 -0.228489 0.511608 0.546136 11.00000 -1.20000 AFIX 0 B2 3 0.566000 0.636333 0.651482 11.00000 0.02586 0.03386 = 0.02967 0.00428 0.00260 -0.00287 O3 5 0.226872 0.681592 0.613370 11.00000 0.02667 0.03489 = 0.03384 0.00061 0.00016 0.00502 C3 1 -0.051120 0.439507 0.572449 11.00000 0.03627 0.03758 = 0.04983 -0.00192 0.00018 -0.00498 AFIX 43 H3 2 -0.128314 0.399118 0.565699 11.00000 -1.20000 AFIX 0 B3 3 0.297935 0.717844 0.645598 11.00000 0.02829 0.03307 = 0.03272 0.00487 0.00342 -0.00199 C4 1 0.122583 0.431295 0.594431 11.00000 0.03919 0.03199 = 0.04293 0.00330 0.00254 0.00273 AFIX 43 H4 2 0.162825 0.385756 0.603794 11.00000 -1.20000 AFIX 0 C5 1 0.232840 0.490102 0.602118 11.00000 0.03013 0.03414 = 0.03183 0.00417 0.00062 0.00499 AFIX 43 H5 2 0.351908 0.484498 0.616786 11.00000 -1.20000 AFIX 0 C6 1 0.419201 0.643311 0.550591 11.00000 0.01860 0.03122 = 0.03345 0.00320 -0.00333 0.00323 C7 1 0.423536 0.597975 0.517033 11.00000 0.02692 0.03235 = 0.03781 -0.00019 0.00064 -0.00212 AFIX 43 H7 2 0.366094 0.552087 0.519234 11.00000 -1.20000 AFIX 0 C8 1 0.509585 0.618038 0.480426 11.00000 0.03127 0.04389 = 0.03463 -0.00474 0.00207 -0.00156 AFIX 43 H8 2 0.509723 0.586035 0.458046 11.00000 -1.20000 AFIX 0 C9 1 0.594933 0.684385 0.476482 11.00000 0.02707 0.04729 = 0.03468 0.00591 0.00295 -0.00110 AFIX 43 H9 2 0.653813 0.698106 0.451479 11.00000 -1.20000 AFIX 0 C10 1 0.593940 0.730671 0.509241 11.00000 0.02465 0.03425 = 0.04201 0.00591 -0.00116 -0.00171 AFIX 43 H10 2 0.652406 0.776359 0.506846 11.00000 -1.20000 AFIX 0 C11 1 0.507351 0.710139 0.545554 11.00000 0.02344 0.03257 = 0.03583 0.00038 -0.00333 0.00194 AFIX 43 H11 2 0.507733 0.742444 0.567792 11.00000 -1.20000 AFIX 0 C12 1 0.756836 0.613121 0.674280 11.00000 0.02539 0.03664 = 0.02699 0.00507 0.00250 -0.00340 C13 1 0.834168 0.544952 0.669593 11.00000 0.03081 0.04020 = 0.03135 0.00057 -0.00099 0.00006 AFIX 43 H13 2 0.772045 0.512609 0.651496 11.00000 -1.20000 AFIX 0 C14 1 0.999930 0.523247 0.690773 11.00000 0.03576 0.04486 = 0.03796 0.00407 -0.00068 0.00838 AFIX 43 H14 2 1.048491 0.476200 0.687592 11.00000 -1.20000 AFIX 0 C15 1 1.094222 0.570491 0.716567 11.00000 0.02910 0.05631 = 0.03921 0.01042 -0.00663 -0.00016 AFIX 43 H15 2 1.207805 0.555967 0.731106 11.00000 -1.20000 AFIX 0 C16 1 1.022421 0.638878 0.721079 11.00000 0.03569 0.04596 = 0.03896 0.00626 -0.00924 -0.01015 AFIX 43 H16 2 1.088009 0.671593 0.738415 11.00000 -1.20000 AFIX 0 C17 1 0.854913 0.659768 0.700347 11.00000 0.03220 0.03503 = 0.03344 0.00529 -0.00064 -0.00509 AFIX 43 H17 2 0.805989 0.706674 0.703945 11.00000 -1.20000 AFIX 0 C18 1 0.185742 0.783791 0.662986 11.00000 0.03278 0.03075 = 0.03539 0.00536 0.00665 -0.00199 C19 1 0.254330 0.819830 0.697272 11.00000 0.04019 0.03659 = 0.04260 0.00048 0.00106 0.00011 AFIX 43 H19 2 0.372298 0.804561 0.709936 11.00000 -1.20000 AFIX 0 C20 1 0.153520 0.877504 0.713199 11.00000 0.05511 0.03895 = 0.04364 -0.00568 0.00290 0.00078 AFIX 43 H20 2 0.201810 0.900987 0.736760 11.00000 -1.20000 AFIX 0 C21 1 -0.016624 0.900841 0.694917 11.00000 0.05587 0.03589 = 0.04736 -0.00028 0.01172 0.00972 AFIX 43 H21 2 -0.084280 0.940941 0.705533 11.00000 -1.20000 AFIX 0 C22 1 -0.088698 0.865699 0.661044 11.00000 0.04276 0.04239 = 0.04938 0.00439 0.00374 0.01185 AFIX 43 H22 2 -0.206689 0.881350 0.648543 11.00000 -1.20000 AFIX 0 C23 1 0.011420 0.807676 0.645391 11.00000 0.03764 0.03634 = 0.03815 0.00221 0.00360 0.00321 AFIX 43 H23 2 -0.039546 0.783691 0.622241 11.00000 -1.20000 AFIX 0 O1 5 0.492253 0.596266 0.620991 11.00000 0.02632 0.03471 = 0.03191 0.00121 -0.00341 0.00440 HKLF 4 REM faces-xstr1656_filtered_a.res in Pbca REM wR2 = 0.0824, GooF = S = 1.036, Restrained GooF = 1.036 for all data REM R1 = 0.0306 for 3408 Fo > 4sig(Fo) and 0.0333 for all 3713 data REM 286 parameters refined using 5 restraints END WGHT 0.0443 0.9773 REM Highest difference peak 0.165, deepest hole -0.180, 1-sigma level 0.033 Q1 1 0.3814 0.6339 0.5734 11.00000 0.05 0.17 Q2 1 0.6717 0.6261 0.6624 11.00000 0.05 0.14 Q3 1 0.2206 0.7463 0.6599 11.00000 0.05 0.13 Q4 1 0.8091 0.6378 0.6826 11.00000 0.05 0.10 Q5 1 0.1876 0.7833 0.6784 11.00000 0.05 0.09 Q6 1 0.7573 0.5829 0.6806 11.00000 0.05 0.09 Q7 1 -0.0794 0.8619 0.6828 11.00000 0.05 0.08 Q8 1 0.2439 0.5866 0.5968 11.00000 0.05 0.08 Q9 1 1.0151 0.6786 0.7635 11.00000 0.05 0.08 Q10 1 0.3853 0.5054 0.6202 11.00000 0.05 0.08 Q11 1 0.4175 0.6803 0.5403 11.00000 0.05 0.08 Q12 1 0.6451 0.6966 0.4991 11.00000 0.05 0.08 Q13 1 0.4568 0.6173 0.5418 11.00000 0.05 0.07 Q14 1 -0.0777 0.5357 0.5784 11.00000 0.05 0.07 Q15 1 0.2869 0.7177 0.6145 11.00000 0.05 0.07 Q16 1 0.8888 0.6397 0.7228 11.00000 0.05 0.07 Q17 1 -0.1840 0.3967 0.5799 11.00000 0.05 0.07 Q18 1 0.7657 0.6232 0.6942 11.00000 0.05 0.07 Q19 1 -0.0395 0.6218 0.5147 11.00000 0.05 0.07 Q20 1 0.5481 0.5558 0.4559 11.00000 0.05 0.07 Q21 1 0.1659 0.8327 0.7228 11.00000 0.05 0.07 ; _shelx_res_checksum 3588 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, 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 N1 N 0.18065(12) 0.55656(5) 0.58979(3) 0.0288(2) Uani 1 1 d . . . . . C1 C 0.00691(15) 0.56541(6) 0.57023(3) 0.0320(2) Uani 1 1 d D . . . . B1 B 0.33439(17) 0.62196(6) 0.59517(4) 0.0292(3) Uani 1 1 d . . . . . O2 O 0.47495(11) 0.69897(4) 0.66311(2) 0.03549(19) Uani 1 1 d . . . . . N2 N -0.04751(15) 0.63109(5) 0.55906(3) 0.0407(2) Uani 1 1 d D . . . . H2N H -0.165(2) 0.6372(8) 0.5482(4) 0.061 Uiso 1 1 d D U . . . H1N H 0.011(2) 0.6680(7) 0.5714(5) 0.061 Uiso 1 1 d D U . . . C2 C -0.10934(17) 0.50568(6) 0.56073(4) 0.0392(3) Uani 1 1 d . . . . . H2 H -0.228489 0.511608 0.546136 0.047 Uiso 1 1 calc R U . . . B2 B 0.56600(18) 0.63633(6) 0.65148(4) 0.0298(3) Uani 1 1 d . . . . . O3 O 0.22687(11) 0.68159(4) 0.61337(2) 0.03180(18) Uani 1 1 d . . . . . C3 C -0.05112(18) 0.43951(6) 0.57245(4) 0.0412(3) Uani 1 1 d . . . . . H3 H -0.128314 0.399118 0.565699 0.049 Uiso 1 1 calc R U . . . B3 B 0.29793(18) 0.71784(6) 0.64560(4) 0.0314(3) Uani 1 1 d . . . . . C4 C 0.12258(18) 0.43129(6) 0.59443(4) 0.0380(3) Uani 1 1 d . . . . . H4 H 0.162825 0.385756 0.603794 0.046 Uiso 1 1 calc R U . . . C5 C 0.23284(16) 0.49010(6) 0.60212(3) 0.0320(2) Uani 1 1 d . . . . . H5 H 0.351908 0.484498 0.616786 0.038 Uiso 1 1 calc R U . . . C6 C 0.41920(14) 0.64331(5) 0.55059(3) 0.0278(2) Uani 1 1 d . . . . . C7 C 0.42354(16) 0.59798(6) 0.51703(3) 0.0324(2) Uani 1 1 d . . . . . H7 H 0.366094 0.552087 0.519234 0.039 Uiso 1 1 calc R U . . . C8 C 0.50959(16) 0.61804(6) 0.48043(4) 0.0366(3) Uani 1 1 d . . . . . H8 H 0.509723 0.586035 0.458046 0.044 Uiso 1 1 calc R U . . . C9 C 0.59493(16) 0.68439(6) 0.47648(3) 0.0363(3) Uani 1 1 d . . . . . H9 H 0.653813 0.698106 0.451479 0.044 Uiso 1 1 calc R U . . . C10 C 0.59394(15) 0.73067(6) 0.50924(3) 0.0336(2) Uani 1 1 d . . . . . H10 H 0.652406 0.776359 0.506846 0.040 Uiso 1 1 calc R U . . . C11 C 0.50735(15) 0.71014(6) 0.54555(3) 0.0306(2) Uani 1 1 d . . . . . H11 H 0.507733 0.742444 0.567792 0.037 Uiso 1 1 calc R U . . . C12 C 0.75684(15) 0.61312(6) 0.67428(3) 0.0297(2) Uani 1 1 d . . . . . C13 C 0.83417(16) 0.54495(6) 0.66959(3) 0.0341(2) Uani 1 1 d . . . . . H13 H 0.772045 0.512609 0.651496 0.041 Uiso 1 1 calc R U . . . C14 C 0.99993(17) 0.52325(7) 0.69077(4) 0.0395(3) Uani 1 1 d . . . . . H14 H 1.048491 0.476200 0.687592 0.047 Uiso 1 1 calc R U . . . C15 C 1.09422(18) 0.57049(7) 0.71657(4) 0.0415(3) Uani 1 1 d . . . . . H15 H 1.207805 0.555967 0.731106 0.050 Uiso 1 1 calc R U . . . C16 C 1.02242(17) 0.63888(7) 0.72108(4) 0.0402(3) Uani 1 1 d . . . . . H16 H 1.088009 0.671593 0.738415 0.048 Uiso 1 1 calc R U . . . C17 C 0.85491(16) 0.65977(6) 0.70035(3) 0.0336(2) Uani 1 1 d . . . . . H17 H 0.805989 0.706674 0.703945 0.040 Uiso 1 1 calc R U . . . C18 C 0.18574(16) 0.78379(6) 0.66299(3) 0.0330(2) Uani 1 1 d . . . . . C19 C 0.25433(19) 0.81983(6) 0.69727(4) 0.0398(3) Uani 1 1 d . . . . . H19 H 0.372298 0.804561 0.709936 0.048 Uiso 1 1 calc R U . . . C20 C 0.1535(2) 0.87750(7) 0.71320(4) 0.0459(3) Uani 1 1 d . . . . . H20 H 0.201810 0.900987 0.736760 0.055 Uiso 1 1 calc R U . . . C21 C -0.0166(2) 0.90084(7) 0.69492(4) 0.0464(3) Uani 1 1 d . . . . . H21 H -0.084280 0.940941 0.705533 0.056 Uiso 1 1 calc R U . . . C22 C -0.0887(2) 0.86570(7) 0.66104(4) 0.0448(3) Uani 1 1 d . . . . . H22 H -0.206689 0.881350 0.648543 0.054 Uiso 1 1 calc R U . . . C23 C 0.01142(17) 0.80768(6) 0.64539(4) 0.0374(3) Uani 1 1 d . . . . . H23 H -0.039546 0.783691 0.622241 0.045 Uiso 1 1 calc R U . . . O1 O 0.49225(10) 0.59627(4) 0.62099(2) 0.03098(18) 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 N1 0.0239(4) 0.0330(5) 0.0296(4) 0.0045(3) 0.0008(3) 0.0019(4) C1 0.0237(5) 0.0368(6) 0.0354(6) 0.0044(4) 0.0003(4) 0.0018(4) B1 0.0241(6) 0.0315(6) 0.0320(6) 0.0014(5) -0.0016(5) 0.0027(5) O2 0.0301(4) 0.0363(4) 0.0401(4) -0.0032(3) -0.0039(3) 0.0025(3) N2 0.0270(5) 0.0379(5) 0.0572(6) 0.0084(5) -0.0112(5) 0.0018(4) C2 0.0277(6) 0.0441(6) 0.0459(6) 0.0009(5) -0.0044(5) -0.0020(5) B2 0.0259(6) 0.0339(6) 0.0297(6) 0.0043(5) 0.0026(5) -0.0029(5) O3 0.0267(4) 0.0349(4) 0.0338(4) 0.0006(3) 0.0002(3) 0.0050(3) C3 0.0363(6) 0.0376(6) 0.0498(7) -0.0019(5) 0.0002(5) -0.0050(5) B3 0.0283(6) 0.0331(6) 0.0327(6) 0.0049(5) 0.0034(5) -0.0020(5) C4 0.0392(6) 0.0320(5) 0.0429(6) 0.0033(5) 0.0025(5) 0.0027(5) C5 0.0301(5) 0.0341(6) 0.0318(5) 0.0042(4) 0.0006(4) 0.0050(4) C6 0.0186(5) 0.0312(5) 0.0334(5) 0.0032(4) -0.0033(4) 0.0032(4) C7 0.0269(5) 0.0323(5) 0.0378(6) -0.0002(4) 0.0006(4) -0.0021(4) C8 0.0313(6) 0.0439(6) 0.0346(6) -0.0047(5) 0.0021(5) -0.0016(5) C9 0.0271(5) 0.0473(6) 0.0347(6) 0.0059(5) 0.0029(4) -0.0011(5) C10 0.0247(5) 0.0342(6) 0.0420(6) 0.0059(4) -0.0012(4) -0.0017(4) C11 0.0234(5) 0.0326(5) 0.0358(6) 0.0004(4) -0.0033(4) 0.0019(4) C12 0.0254(5) 0.0366(6) 0.0270(5) 0.0051(4) 0.0025(4) -0.0034(4) C13 0.0308(6) 0.0402(6) 0.0313(5) 0.0006(4) -0.0010(4) 0.0001(5) C14 0.0358(6) 0.0449(7) 0.0380(6) 0.0041(5) -0.0007(5) 0.0084(5) C15 0.0291(6) 0.0563(7) 0.0392(6) 0.0104(5) -0.0066(5) -0.0002(5) C16 0.0357(6) 0.0460(7) 0.0390(6) 0.0063(5) -0.0092(5) -0.0102(5) C17 0.0322(6) 0.0350(6) 0.0334(5) 0.0053(4) -0.0006(5) -0.0051(5) C18 0.0328(6) 0.0308(5) 0.0354(6) 0.0054(4) 0.0066(4) -0.0020(5) C19 0.0402(6) 0.0366(6) 0.0426(6) 0.0005(5) 0.0011(5) 0.0001(5) C20 0.0551(8) 0.0389(6) 0.0436(7) -0.0057(5) 0.0029(6) 0.0008(6) C21 0.0559(8) 0.0359(6) 0.0474(7) -0.0003(5) 0.0117(6) 0.0097(6) C22 0.0428(7) 0.0424(7) 0.0494(7) 0.0044(5) 0.0037(6) 0.0119(6) C23 0.0376(6) 0.0363(6) 0.0382(6) 0.0022(5) 0.0036(5) 0.0032(5) O1 0.0263(4) 0.0347(4) 0.0319(4) 0.0012(3) -0.0034(3) 0.0044(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -12 -2 0.0619 0 12 2 0.0534 -4 0 12 0.0988 4 0 -12 0.0846 0 0 -21 0.0137 0 0 21 0.0261 -4 1 -8 0.1054 3 -1 14 0.0882 0 -5 -20 0.0298 -4 -4 -7 0.1118 0 -9 14 0.0565 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 C1 N1 C5 118.79(9) . . ? C1 N1 B1 121.44(8) . . ? C5 N1 B1 119.56(9) . . ? N2 C1 N1 118.95(10) . . ? N2 C1 C2 121.16(10) . . ? N1 C1 C2 119.86(10) . . ? O1 B1 O3 112.72(9) . . ? O1 B1 C6 110.16(9) . . ? O3 B1 C6 110.89(8) . . ? O1 B1 N1 106.86(8) . . ? O3 B1 N1 107.45(8) . . ? C6 B1 N1 108.56(8) . . ? B3 O2 B2 119.63(9) . . ? C3 C2 C1 120.09(11) . . ? O1 B2 O2 120.79(10) . . ? O1 B2 C12 120.64(10) . . ? O2 B2 C12 118.57(10) . . ? B3 O3 B1 121.76(9) . . ? C2 C3 C4 119.66(11) . . ? O3 B3 O2 120.68(10) . . ? O3 B3 C18 120.73(10) . . ? O2 B3 C18 118.55(10) . . ? C5 C4 C3 118.37(10) . . ? C4 C5 N1 123.10(10) . . ? C7 C6 C11 116.43(10) . . ? C7 C6 B1 124.72(9) . . ? C11 C6 B1 118.69(9) . . ? C8 C7 C6 121.83(10) . . ? C9 C8 C7 120.23(11) . . ? C8 C9 C10 119.48(10) . . ? C9 C10 C11 119.77(10) . . ? C10 C11 C6 122.25(10) . . ? C13 C12 C17 117.63(10) . . ? C13 C12 B2 121.22(10) . . ? C17 C12 B2 121.15(10) . . ? C14 C13 C12 121.50(11) . . ? C15 C14 C13 119.73(11) . . ? C16 C15 C14 119.78(11) . . ? C15 C16 C17 120.13(11) . . ? C16 C17 C12 121.20(11) . . ? C19 C18 C23 117.62(10) . . ? C19 C18 B3 121.03(10) . . ? C23 C18 B3 121.33(10) . . ? C20 C19 C18 121.22(12) . . ? C21 C20 C19 120.12(12) . . ? C20 C21 C22 119.83(11) . . ? C21 C22 C23 119.94(12) . . ? C22 C23 C18 121.26(12) . . ? B2 O1 B1 121.57(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 N1 C1 1.3579(14) . ? N1 C5 1.3605(13) . ? N1 B1 1.6251(15) . ? C1 N2 1.3401(15) . ? C1 C2 1.4093(16) . ? B1 O1 1.4531(13) . ? B1 O3 1.4667(14) . ? B1 C6 1.6251(15) . ? O2 B3 1.3833(15) . ? O2 B2 1.3848(14) . ? C2 C3 1.3611(17) . ? B2 O1 1.3504(14) . ? B2 C12 1.5635(16) . ? O3 B3 1.3492(15) . ? C3 C4 1.3958(17) . ? B3 C18 1.5646(16) . ? C4 C5 1.3604(16) . ? C6 C7 1.3938(15) . ? C6 C11 1.4023(15) . ? C7 C8 1.3903(16) . ? C8 C9 1.3822(17) . ? C9 C10 1.3840(16) . ? C10 C11 1.3860(15) . ? C12 C13 1.3940(16) . ? C12 C17 1.3962(15) . ? C13 C14 1.3886(16) . ? C14 C15 1.3857(18) . ? C15 C16 1.3834(18) . ? C16 C17 1.3866(16) . ? C18 C19 1.3952(16) . ? C18 C23 1.3959(16) . ? C19 C20 1.3861(17) . ? C20 C21 1.378(2) . ? C21 C22 1.3843(19) . ? C22 C23 1.3856(17) . ? 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 C5 N1 C1 N2 178.15(10) . . . . ? B1 N1 C1 N2 -7.25(15) . . . . ? C5 N1 C1 C2 -4.13(15) . . . . ? B1 N1 C1 C2 170.48(10) . . . . ? C1 N1 B1 O1 173.92(9) . . . . ? C5 N1 B1 O1 -11.51(12) . . . . ? C1 N1 B1 O3 52.70(12) . . . . ? C5 N1 B1 O3 -132.73(9) . . . . ? C1 N1 B1 C6 -67.29(12) . . . . ? C5 N1 B1 C6 107.28(10) . . . . ? N2 C1 C2 C3 -179.92(12) . . . . ? N1 C1 C2 C3 2.40(18) . . . . ? B3 O2 B2 O1 5.29(15) . . . . ? B3 O2 B2 C12 -175.01(9) . . . . ? O1 B1 O3 B3 14.38(14) . . . . ? C6 B1 O3 B3 -109.65(10) . . . . ? N1 B1 O3 B3 131.85(9) . . . . ? C1 C2 C3 C4 0.98(19) . . . . ? B1 O3 B3 O2 -1.06(15) . . . . ? B1 O3 B3 C18 176.72(9) . . . . ? B2 O2 B3 O3 -9.54(15) . . . . ? B2 O2 B3 C18 172.63(9) . . . . ? C2 C3 C4 C5 -2.53(18) . . . . ? C3 C4 C5 N1 0.76(17) . . . . ? C1 N1 C5 C4 2.59(16) . . . . ? B1 N1 C5 C4 -172.12(10) . . . . ? O1 B1 C6 C7 93.46(12) . . . . ? O3 B1 C6 C7 -141.05(10) . . . . ? N1 B1 C6 C7 -23.22(13) . . . . ? O1 B1 C6 C11 -81.87(11) . . . . ? O3 B1 C6 C11 43.62(13) . . . . ? N1 B1 C6 C11 161.44(8) . . . . ? C11 C6 C7 C8 -0.37(15) . . . . ? B1 C6 C7 C8 -175.80(10) . . . . ? C6 C7 C8 C9 0.28(17) . . . . ? C7 C8 C9 C10 -0.04(17) . . . . ? C8 C9 C10 C11 -0.10(16) . . . . ? C9 C10 C11 C6 0.00(16) . . . . ? C7 C6 C11 C10 0.23(15) . . . . ? B1 C6 C11 C10 175.95(9) . . . . ? O1 B2 C12 C13 -12.67(15) . . . . ? O2 B2 C12 C13 167.63(10) . . . . ? O1 B2 C12 C17 167.90(10) . . . . ? O2 B2 C12 C17 -11.80(15) . . . . ? C17 C12 C13 C14 1.59(16) . . . . ? B2 C12 C13 C14 -177.86(10) . . . . ? C12 C13 C14 C15 -1.42(17) . . . . ? C13 C14 C15 C16 0.09(18) . . . . ? C14 C15 C16 C17 0.99(18) . . . . ? C15 C16 C17 C12 -0.79(17) . . . . ? C13 C12 C17 C16 -0.48(16) . . . . ? B2 C12 C17 C16 178.97(10) . . . . ? O3 B3 C18 C19 177.47(10) . . . . ? O2 B3 C18 C19 -4.70(16) . . . . ? O3 B3 C18 C23 -1.04(16) . . . . ? O2 B3 C18 C23 176.80(10) . . . . ? C23 C18 C19 C20 -0.29(17) . . . . ? B3 C18 C19 C20 -178.85(11) . . . . ? C18 C19 C20 C21 -0.75(19) . . . . ? C19 C20 C21 C22 1.22(19) . . . . ? C20 C21 C22 C23 -0.66(19) . . . . ? C21 C22 C23 C18 -0.40(19) . . . . ? C19 C18 C23 C22 0.86(17) . . . . ? B3 C18 C23 C22 179.42(11) . . . . ? O2 B2 O1 B1 9.61(15) . . . . ? C12 B2 O1 B1 -170.08(9) . . . . ? O3 B1 O1 B2 -18.62(14) . . . . ? C6 B1 O1 B2 105.82(11) . . . . ? N1 B1 O1 B2 -136.44(9) . . . . ?