#------------------------------------------------------------------------------ #$Date: 2019-06-12 03:25:16 +0300 (Wed, 12 Jun 2019) $ #$Revision: 215852 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/13/1551350.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_1551350 loop_ _publ_author_name 'Brueckner, Tobias' 'Dewhurst, Rian David' 'Dellermann, Theresa' 'M\"uller, Marcel' 'Braunschweig, Holger' _publ_section_title ; Mild Synthesis of Diboryldiborenes by Diboration of B-B Triple Bonds ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC02544H _journal_year 2019 _chemical_formula_moiety 'C58 H68 B4 N4 O4' _chemical_formula_sum 'C58 H68 B4 N4 O4' _chemical_formula_weight 928.40 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-11-29 deposited with the CCDC. 2019-06-10 downloaded from the CCDC. ; _cell_angle_alpha 73.5300(10) _cell_angle_beta 80.5900(10) _cell_angle_gamma 64.8320(10) _cell_formula_units_Z 1 _cell_length_a 10.9190(4) _cell_length_b 11.0985(4) _cell_length_c 12.1024(5) _cell_measurement_reflns_used 9431 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.68 _cell_measurement_theta_min 2.39 _cell_volume 1271.37(8) _computing_cell_refinement 'Saint+ ver. V8.37A (Bruker AXS)' _computing_data_collection 'APEX2 ver. 2014.9 (Bruker AXS)' _computing_data_reduction 'Saint+ ver. V8.37A (Bruker AXS)' _computing_molecular_graphics 'ShelXLe (Huebschle et all, 2011)' _computing_publication_material 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'CMOS area detector (Photon II)' _diffrn_detector_area_resol_mean 7.5 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker D8 Quest' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'multi-layer mirror' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0831 _diffrn_reflns_av_unetI/netI 0.0613 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 37692 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 26.369 _diffrn_reflns_theta_min 2.063 _diffrn_source 'microfocus sealed tube (Incoatec ImS)' _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6557 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SadAbs 2016/2 (Bruker AXS)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.213 _exptl_crystal_description block _exptl_crystal_F_000 496 _exptl_crystal_size_max 0.361 _exptl_crystal_size_mid 0.310 _exptl_crystal_size_min 0.245 _refine_diff_density_max 0.236 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 320 _refine_ls_number_reflns 5176 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0558 _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^)+(0.0403P)^2^+0.7219P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1077 _refine_ls_wR_factor_ref 0.1269 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3534 _reflns_number_total 5176 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc02544h2.cif _cod_data_source_block 2a _cod_database_code 1551350 _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. ; _shelx_res_file ; ToBr006.res created by SHELXL-2014/7 TITL test_a.res in P-1 REM Old TITL test in P-1 REM SHELXT solution in P-1 REM R1 0.174, Rweak 0.016, Alpha 0.045, Orientation as input REM Formula found by SHELXT: C31 N2 O2 CELL 0.71073 10.9190 11.0985 12.1024 73.530 80.590 64.832 ZERR 1.000 0.0004 0.0004 0.0005 0.001 0.001 0.001 LATT 1 SFAC C H B N O UNIT 58 68 4 4 4 TEMP -173.150 L.S. 10 BOND $H acta 52 shel 999 0.8 LIST 4 FMAP 2 PLAN 20 WGHT 0.040300 0.721900 FVAR 0.81472 O1 5 0.729024 0.435373 0.642144 11.00000 0.02373 0.02200 = 0.02377 -0.00307 -0.00410 -0.01326 B1 3 0.626343 0.385186 0.651299 11.00000 0.02315 0.01604 = 0.02415 -0.00779 0.00375 -0.01032 O2 5 0.645208 0.281295 0.756794 11.00000 0.02751 0.02285 = 0.02634 -0.00197 -0.00598 -0.01579 B2 3 0.516293 0.433111 0.552539 11.00000 0.02021 0.01761 = 0.02178 -0.00816 0.00235 -0.00822 N1 4 0.321277 0.350620 0.628630 11.00000 0.02118 0.01503 = 0.02212 -0.00608 0.00040 -0.01080 N2 4 0.458012 0.252561 0.496757 11.00000 0.01906 0.01660 = 0.02530 -0.00829 0.00156 -0.00961 C1 1 0.805457 0.363481 0.737187 11.00000 0.02175 0.01844 = 0.01994 -0.00646 -0.00229 -0.00687 C2 1 0.280335 0.404669 0.730519 11.00000 0.02030 0.02182 = 0.02212 -0.00950 0.00289 -0.01265 C3 1 0.433739 0.343204 0.560736 11.00000 0.01906 0.01323 = 0.01858 -0.00210 -0.00330 -0.00480 C4 1 0.755626 0.270008 0.806069 11.00000 0.02196 0.02106 = 0.02656 -0.00667 -0.00418 -0.01095 C5 1 0.583319 0.187550 0.434579 11.00000 0.02242 0.01617 = 0.02719 -0.00961 0.00342 -0.01105 C6 1 0.195962 0.543196 0.722811 11.00000 0.02149 0.02044 = 0.02753 -0.00852 -0.00022 -0.01128 C7 1 0.695722 0.088403 0.497878 11.00000 0.02436 0.01602 = 0.03068 -0.01001 0.00139 -0.01142 C8 1 0.813328 0.020965 0.436796 11.00000 0.02250 0.01837 = 0.04177 -0.01341 0.00127 -0.00907 AFIX 43 H00C 2 0.891650 -0.043316 0.477494 11.00000 -1.20000 AFIX 0 C9 1 0.258204 0.265751 0.607732 11.00000 0.02250 0.01790 = 0.02914 -0.00659 -0.00122 -0.01225 AFIX 23 H00A 2 0.169305 0.323469 0.573108 11.00000 -1.20000 H00B 2 0.245770 0.201853 0.680154 11.00000 -1.20000 AFIX 0 C10 1 0.916445 0.374778 0.766497 11.00000 0.02275 0.02854 = 0.02843 -0.00933 0.00105 -0.01380 AFIX 43 H00E 2 0.950660 0.439064 0.719067 11.00000 -1.20000 AFIX 0 C11 1 0.153573 0.645751 0.609414 11.00000 0.02324 0.01724 = 0.03063 -0.00751 0.00200 -0.00996 AFIX 23 H00D 2 0.232927 0.628699 0.553910 11.00000 -1.20000 H00F 2 0.126053 0.738819 0.620879 11.00000 -1.20000 AFIX 0 C12 1 0.321549 0.311564 0.836802 11.00000 0.02131 0.02593 = 0.02435 -0.00565 0.00021 -0.01438 C13 1 0.975906 0.287759 0.868631 11.00000 0.02216 0.02969 = 0.03172 -0.01262 -0.00459 -0.00939 AFIX 43 H00H 2 1.052170 0.293074 0.891746 11.00000 -1.20000 AFIX 0 C14 1 0.413324 0.161709 0.847971 11.00000 0.02388 0.02361 = 0.02644 -0.00127 -0.00238 -0.00932 AFIX 23 H00G 2 0.496797 0.141295 0.884757 11.00000 -1.20000 H00I 2 0.439929 0.144540 0.769839 11.00000 -1.20000 AFIX 0 C15 1 0.817854 0.046113 0.317892 11.00000 0.02703 0.02434 = 0.04253 -0.01756 0.01050 -0.01332 AFIX 43 H00J 2 0.898920 -0.000615 0.277563 11.00000 -1.20000 AFIX 0 C16 1 0.584766 0.211052 0.315109 11.00000 0.03104 0.01845 = 0.02970 -0.00907 0.00166 -0.01358 C17 1 0.359607 0.188434 0.524126 11.00000 0.02608 0.02171 = 0.03163 -0.01188 0.00266 -0.01484 AFIX 23 H00K 2 0.403507 0.089324 0.560628 11.00000 -1.20000 H00L 2 0.315728 0.200630 0.454033 11.00000 -1.20000 AFIX 0 C18 1 0.037721 0.642664 0.556535 11.00000 0.02685 0.02082 = 0.03674 -0.00176 -0.00389 -0.00991 AFIX 137 H00M 2 0.016409 0.712232 0.483419 11.00000 -1.50000 H00N 2 -0.042394 0.661939 0.609743 11.00000 -1.50000 H00O 2 0.064687 0.551838 0.542456 11.00000 -1.50000 AFIX 0 C19 1 0.813809 0.183217 0.906862 11.00000 0.03898 0.02312 = 0.02766 0.00034 -0.00695 -0.01728 AFIX 43 H00P 2 0.779099 0.119065 0.953727 11.00000 -1.20000 AFIX 0 C20 1 0.686230 0.049979 0.628021 11.00000 0.03051 0.01987 = 0.03323 -0.00983 -0.00257 -0.00655 AFIX 23 H00Q 2 0.634459 0.135067 0.655141 11.00000 -1.20000 H00R 2 0.633124 -0.007364 0.652938 11.00000 -1.20000 AFIX 0 C21 1 0.926450 0.193567 0.937368 11.00000 0.03403 0.02484 = 0.02934 -0.00590 -0.01177 -0.00841 AFIX 43 H00S 2 0.969726 0.135046 1.006344 11.00000 -1.20000 AFIX 0 C22 1 0.348263 0.064005 0.918588 11.00000 0.03132 0.02547 = 0.03197 -0.00135 -0.00121 -0.01302 AFIX 137 H00T 2 0.413354 -0.030989 0.923757 11.00000 -1.50000 H00U 2 0.267744 0.080601 0.880922 11.00000 -1.50000 H00V 2 0.322028 0.079839 0.996305 11.00000 -1.50000 AFIX 0 C23 1 0.277210 0.359971 0.936719 11.00000 0.03577 0.03647 = 0.02187 -0.00625 -0.00104 -0.02036 AFIX 43 H00W 2 0.305023 0.298726 1.009499 11.00000 -1.20000 AFIX 0 C24 1 0.154040 0.585778 0.825656 11.00000 0.03127 0.02488 = 0.03505 -0.01427 0.00349 -0.01115 AFIX 43 H00X 2 0.096893 0.679190 0.822965 11.00000 -1.20000 AFIX 0 C25 1 0.462094 0.307426 0.245391 11.00000 0.03676 0.02861 = 0.02806 -0.00948 -0.00266 -0.01221 AFIX 23 H00Y 2 0.389319 0.356718 0.296845 11.00000 -1.20000 H00Z 2 0.428837 0.252623 0.216071 11.00000 -1.20000 AFIX 0 C26 1 0.704931 0.138851 0.257883 11.00000 0.03799 0.02495 = 0.02863 -0.01273 0.00895 -0.01613 AFIX 43 H010 2 0.708501 0.154172 0.176329 11.00000 -1.20000 AFIX 0 C27 1 0.193364 0.495824 0.931257 11.00000 0.04064 0.03992 = 0.02898 -0.01994 0.00627 -0.01943 AFIX 43 H011 2 0.162764 0.527378 1.000061 11.00000 -1.20000 AFIX 0 C28 1 0.489322 0.412017 0.143986 11.00000 0.04933 0.03653 = 0.03187 -0.00296 0.00297 -0.00997 AFIX 137 H012 2 0.405028 0.473231 0.104935 11.00000 -1.50000 H013 2 0.556724 0.364414 0.089700 11.00000 -1.50000 H014 2 0.523777 0.465869 0.171916 11.00000 -1.50000 AFIX 0 C29 1 0.817855 -0.025647 0.687747 11.00000 0.04698 0.09540 = 0.04792 -0.03727 -0.01855 0.02277 AFIX 137 H015 2 0.799526 -0.037897 0.771315 11.00000 -1.50000 H016 2 0.874102 0.027259 0.661220 11.00000 -1.50000 H017 2 0.865700 -0.115576 0.669621 11.00000 -1.50000 AFIX 0 HKLF 4 REM test_a.res in P-1 REM R1 = 0.0558 for 3534 Fo > 4sig(Fo) and 0.0987 for all 5176 data REM 320 parameters refined using 0 restraints END WGHT 0.0403 0.7219 REM Highest difference peak 0.236, deepest hole -0.266, 1-sigma level 0.053 Q1 1 0.7272 -0.0585 0.7001 11.00000 0.05 0.24 Q2 1 0.9310 -0.1003 0.6568 11.00000 0.05 0.22 Q3 1 0.5436 0.4414 0.6082 11.00000 0.05 0.21 Q4 1 0.6432 0.1565 0.4663 11.00000 0.05 0.21 Q5 1 0.3746 0.2388 0.2798 11.00000 0.05 0.20 Q6 1 0.9220 -0.0611 0.5231 11.00000 0.05 0.19 Q7 1 0.4634 0.3183 0.1338 11.00000 0.05 0.19 Q8 1 0.4616 -0.0003 1.0345 11.00000 0.05 0.19 Q9 1 0.9622 -0.0940 0.8136 11.00000 0.05 0.18 Q10 1 0.6396 0.1930 0.2824 11.00000 0.05 0.18 Q11 1 0.0604 0.5389 0.5175 11.00000 0.05 0.18 Q12 1 0.8935 0.5706 0.7049 11.00000 0.05 0.18 Q13 1 0.8940 -0.0986 0.8820 11.00000 0.05 0.17 Q14 1 0.5653 0.4177 0.5193 11.00000 0.05 0.17 Q15 1 0.6188 0.3468 0.5910 11.00000 0.05 0.17 Q16 1 0.1948 0.3178 1.0980 11.00000 0.05 0.17 Q17 1 0.1747 0.3572 0.5168 11.00000 0.05 0.17 Q18 1 0.9776 -0.0434 0.5703 11.00000 0.05 0.16 Q19 1 0.4843 0.5066 0.5510 11.00000 0.05 0.16 Q20 1 0.3403 0.4581 0.1092 11.00000 0.05 0.16 ; _shelx_res_checksum 62966 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 O1 O 0.72902(13) 0.43537(14) 0.64214(11) 0.0219(3) Uani 1 1 d . . B1 B 0.6263(2) 0.3852(2) 0.6513(2) 0.0202(5) Uani 1 1 d . . O2 O 0.64521(13) 0.28129(14) 0.75679(12) 0.0238(3) Uani 1 1 d . . B2 B 0.5163(2) 0.4331(2) 0.5525(2) 0.0193(5) Uani 1 1 d . . N1 N 0.32128(15) 0.35062(16) 0.62863(14) 0.0180(4) Uani 1 1 d . . N2 N 0.45801(15) 0.25256(16) 0.49676(14) 0.0190(4) Uani 1 1 d . . C1 C 0.80546(19) 0.3635(2) 0.73719(17) 0.0199(4) Uani 1 1 d . . C2 C 0.28033(19) 0.4047(2) 0.73052(17) 0.0195(4) Uani 1 1 d . . C3 C 0.43374(19) 0.34320(19) 0.56074(16) 0.0176(4) Uani 1 1 d . . C4 C 0.75563(19) 0.2700(2) 0.80607(18) 0.0218(5) Uani 1 1 d . . C5 C 0.58332(19) 0.1876(2) 0.43458(18) 0.0203(4) Uani 1 1 d . . C6 C 0.19596(19) 0.5432(2) 0.72281(18) 0.0216(5) Uani 1 1 d . . C7 C 0.6957(2) 0.0884(2) 0.49788(18) 0.0219(5) Uani 1 1 d . . C8 C 0.8133(2) 0.0210(2) 0.4368(2) 0.0262(5) Uani 1 1 d . . H00C H 0.8917 -0.0433 0.4775 0.031 Uiso 1 1 calc R U C9 C 0.2582(2) 0.2658(2) 0.60773(18) 0.0215(5) Uani 1 1 d . . H00A H 0.1693 0.3235 0.5731 0.026 Uiso 1 1 calc R U H00B H 0.2458 0.2019 0.6802 0.026 Uiso 1 1 calc R U C10 C 0.9164(2) 0.3748(2) 0.76650(18) 0.0250(5) Uani 1 1 d . . H00E H 0.9507 0.4391 0.7191 0.030 Uiso 1 1 calc R U C11 C 0.1536(2) 0.6458(2) 0.60941(18) 0.0231(5) Uani 1 1 d . . H00D H 0.2329 0.6287 0.5539 0.028 Uiso 1 1 calc R U H00F H 0.1261 0.7388 0.6209 0.028 Uiso 1 1 calc R U C12 C 0.3215(2) 0.3116(2) 0.83680(18) 0.0224(5) Uani 1 1 d . . C13 C 0.9759(2) 0.2878(2) 0.86863(19) 0.0266(5) Uani 1 1 d . . H00H H 1.0522 0.2931 0.8917 0.032 Uiso 1 1 calc R U C14 C 0.4133(2) 0.1617(2) 0.84797(19) 0.0256(5) Uani 1 1 d . . H00G H 0.4968 0.1413 0.8848 0.031 Uiso 1 1 calc R U H00I H 0.4399 0.1445 0.7698 0.031 Uiso 1 1 calc R U C15 C 0.8179(2) 0.0461(2) 0.3179(2) 0.0296(5) Uani 1 1 d . . H00J H 0.8989 -0.0006 0.2776 0.036 Uiso 1 1 calc R U C16 C 0.5848(2) 0.2111(2) 0.31511(18) 0.0247(5) Uani 1 1 d . . C17 C 0.3596(2) 0.1884(2) 0.52413(18) 0.0239(5) Uani 1 1 d . . H00K H 0.4035 0.0893 0.5606 0.029 Uiso 1 1 calc R U H00L H 0.3157 0.2006 0.4540 0.029 Uiso 1 1 calc R U C18 C 0.0377(2) 0.6427(2) 0.5565(2) 0.0289(5) Uani 1 1 d . . H00M H 0.0164 0.7122 0.4834 0.043 Uiso 1 1 calc R U H00N H -0.0424 0.6619 0.6097 0.043 Uiso 1 1 calc R U H00O H 0.0647 0.5518 0.5425 0.043 Uiso 1 1 calc R U C19 C 0.8138(2) 0.1832(2) 0.90686(19) 0.0290(5) Uani 1 1 d . . H00P H 0.7791 0.1191 0.9537 0.035 Uiso 1 1 calc R U C20 C 0.6862(2) 0.0500(2) 0.62802(19) 0.0282(5) Uani 1 1 d . . H00Q H 0.6345 0.1351 0.6551 0.034 Uiso 1 1 calc R U H00R H 0.6331 -0.0074 0.6529 0.034 Uiso 1 1 calc R U C21 C 0.9264(2) 0.1936(2) 0.93737(19) 0.0295(5) Uani 1 1 d . . H00S H 0.9697 0.1350 1.0063 0.035 Uiso 1 1 calc R U C22 C 0.3483(2) 0.0640(2) 0.91859(19) 0.0303(5) Uani 1 1 d . . H00T H 0.4134 -0.0310 0.9238 0.045 Uiso 1 1 calc R U H00U H 0.2677 0.0806 0.8809 0.045 Uiso 1 1 calc R U H00V H 0.3220 0.0798 0.9963 0.045 Uiso 1 1 calc R U C23 C 0.2772(2) 0.3600(2) 0.93672(19) 0.0295(5) Uani 1 1 d . . H00W H 0.3050 0.2987 1.0095 0.035 Uiso 1 1 calc R U C24 C 0.1540(2) 0.5858(2) 0.82566(19) 0.0295(5) Uani 1 1 d . . H00X H 0.0969 0.6792 0.8230 0.035 Uiso 1 1 calc R U C25 C 0.4621(2) 0.3074(2) 0.24539(19) 0.0307(5) Uani 1 1 d . . H00Y H 0.3893 0.3567 0.2968 0.037 Uiso 1 1 calc R U H00Z H 0.4288 0.2526 0.2161 0.037 Uiso 1 1 calc R U C26 C 0.7049(2) 0.1389(2) 0.2579(2) 0.0292(5) Uani 1 1 d . . H010 H 0.7085 0.1542 0.1763 0.035 Uiso 1 1 calc R U C27 C 0.1934(2) 0.4958(2) 0.9313(2) 0.0337(6) Uani 1 1 d . . H011 H 0.1628 0.5274 1.0001 0.040 Uiso 1 1 calc R U C28 C 0.4893(3) 0.4120(3) 0.1440(2) 0.0436(7) Uani 1 1 d . . H012 H 0.4050 0.4732 0.1049 0.065 Uiso 1 1 calc R U H013 H 0.5567 0.3644 0.0897 0.065 Uiso 1 1 calc R U H014 H 0.5238 0.4659 0.1719 0.065 Uiso 1 1 calc R U C29 C 0.8179(3) -0.0256(4) 0.6877(3) 0.0752(11) Uani 1 1 d . . H015 H 0.7995 -0.0379 0.7713 0.113 Uiso 1 1 calc R U H016 H 0.8741 0.0273 0.6612 0.113 Uiso 1 1 calc R U H017 H 0.8657 -0.1156 0.6696 0.113 Uiso 1 1 calc R U 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 0.0237(7) 0.0220(8) 0.0238(8) -0.0031(6) -0.0041(6) -0.0133(6) B1 0.0231(12) 0.0160(12) 0.0242(13) -0.0078(10) 0.0037(10) -0.0103(10) O2 0.0275(8) 0.0229(8) 0.0263(8) -0.0020(6) -0.0060(6) -0.0158(6) B2 0.0202(12) 0.0176(12) 0.0218(13) -0.0082(10) 0.0023(9) -0.0082(9) N1 0.0212(9) 0.0150(9) 0.0221(9) -0.0061(7) 0.0004(7) -0.0108(7) N2 0.0191(8) 0.0166(9) 0.0253(10) -0.0083(7) 0.0016(7) -0.0096(7) C1 0.0218(10) 0.0184(11) 0.0199(11) -0.0065(8) -0.0023(8) -0.0069(8) C2 0.0203(10) 0.0218(11) 0.0221(11) -0.0095(9) 0.0029(8) -0.0127(9) C3 0.0191(10) 0.0132(10) 0.0186(11) -0.0021(8) -0.0033(8) -0.0048(8) C4 0.0220(11) 0.0211(11) 0.0266(12) -0.0067(9) -0.0042(9) -0.0109(9) C5 0.0224(11) 0.0162(10) 0.0272(12) -0.0096(9) 0.0034(9) -0.0111(8) C6 0.0215(10) 0.0204(11) 0.0275(12) -0.0085(9) -0.0002(9) -0.0113(9) C7 0.0244(11) 0.0160(10) 0.0307(12) -0.0100(9) 0.0014(9) -0.0114(9) C8 0.0225(11) 0.0184(11) 0.0418(14) -0.0134(10) 0.0013(10) -0.0091(9) C9 0.0225(11) 0.0179(11) 0.0291(12) -0.0066(9) -0.0012(9) -0.0122(9) C10 0.0228(11) 0.0285(12) 0.0284(12) -0.0093(10) 0.0010(9) -0.0138(9) C11 0.0232(11) 0.0172(11) 0.0306(12) -0.0075(9) 0.0020(9) -0.0100(9) C12 0.0213(10) 0.0259(12) 0.0244(12) -0.0056(9) 0.0002(9) -0.0144(9) C13 0.0222(11) 0.0297(12) 0.0317(13) -0.0126(10) -0.0046(9) -0.0094(9) C14 0.0239(11) 0.0236(12) 0.0264(12) -0.0013(9) -0.0024(9) -0.0093(9) C15 0.0270(12) 0.0243(12) 0.0425(15) -0.0176(10) 0.0105(10) -0.0133(10) C16 0.0310(12) 0.0184(11) 0.0297(13) -0.0091(9) 0.0017(9) -0.0136(9) C17 0.0261(11) 0.0217(11) 0.0316(12) -0.0119(9) 0.0027(9) -0.0148(9) C18 0.0268(12) 0.0208(12) 0.0367(13) -0.0018(10) -0.0039(10) -0.0099(9) C19 0.0390(13) 0.0231(12) 0.0277(13) 0.0003(9) -0.0070(10) -0.0173(10) C20 0.0305(12) 0.0199(11) 0.0332(13) -0.0098(10) -0.0026(10) -0.0066(9) C21 0.0340(12) 0.0248(12) 0.0293(13) -0.0059(10) -0.0118(10) -0.0084(10) C22 0.0313(12) 0.0255(12) 0.0320(13) -0.0013(10) -0.0012(10) -0.0130(10) C23 0.0358(13) 0.0365(14) 0.0219(12) -0.0062(10) -0.0010(10) -0.0204(11) C24 0.0313(12) 0.0249(12) 0.0351(14) -0.0143(10) 0.0035(10) -0.0112(10) C25 0.0368(13) 0.0286(13) 0.0281(13) -0.0095(10) -0.0027(10) -0.0122(10) C26 0.0380(13) 0.0250(12) 0.0286(13) -0.0127(10) 0.0089(10) -0.0161(10) C27 0.0406(14) 0.0399(14) 0.0290(13) -0.0199(11) 0.0063(11) -0.0194(11) C28 0.0493(16) 0.0365(15) 0.0319(14) -0.0030(11) 0.0030(12) -0.0100(12) C29 0.0470(18) 0.095(3) 0.0479(19) -0.0373(18) -0.0185(14) 0.0228(17) 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' 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 C1 O1 B1 107.34(15) . . O1 B1 O2 106.65(17) . . O1 B1 B2 125.08(18) . . O2 B1 B2 128.13(18) . . C4 O2 B1 107.24(15) . . C3 B2 B2 116.2(2) . 2_666 C3 B2 B1 118.64(17) . . B2 B2 B1 125.1(2) 2_666 . C3 N1 C2 125.97(16) . . C3 N1 C9 112.57(15) . . C2 N1 C9 119.79(15) . . C3 N2 C5 126.81(16) . . C3 N2 C17 112.61(15) . . C5 N2 C17 117.99(15) . . O1 C1 C10 128.90(19) . . O1 C1 C4 109.52(16) . . C10 C1 C4 121.58(19) . . C6 C2 C12 121.86(19) . . C6 C2 N1 120.70(18) . . C12 C2 N1 117.33(17) . . N1 C3 N2 108.28(16) . . N1 C3 B2 125.14(17) . . N2 C3 B2 126.46(17) . . C19 C4 O2 128.79(19) . . C19 C4 C1 121.98(19) . . O2 C4 C1 109.23(17) . . C16 C5 C7 121.55(18) . . C16 C5 N2 119.21(18) . . C7 C5 N2 118.70(18) . . C24 C6 C2 117.33(19) . . C24 C6 C11 119.90(18) . . C2 C6 C11 122.75(18) . . C8 C7 C5 118.02(19) . . C8 C7 C20 120.90(19) . . C5 C7 C20 120.96(18) . . C15 C8 C7 121.1(2) . . C15 C8 H00C 119.5 . . C7 C8 H00C 119.5 . . N1 C9 C17 103.17(15) . . N1 C9 H00A 111.1 . . C17 C9 H00A 111.1 . . N1 C9 H00B 111.1 . . C17 C9 H00B 111.1 . . H00A C9 H00B 109.1 . . C1 C10 C13 117.0(2) . . C1 C10 H00E 121.5 . . C13 C10 H00E 121.5 . . C6 C11 C18 114.67(17) . . C6 C11 H00D 108.6 . . C18 C11 H00D 108.6 . . C6 C11 H00F 108.6 . . C18 C11 H00F 108.6 . . H00D C11 H00F 107.6 . . C23 C12 C2 118.33(19) . . C23 C12 C14 118.52(19) . . C2 C12 C14 123.15(18) . . C21 C13 C10 121.48(19) . . C21 C13 H00H 119.3 . . C10 C13 H00H 119.3 . . C12 C14 C22 113.61(17) . . C12 C14 H00G 108.8 . . C22 C14 H00G 108.8 . . C12 C14 H00I 108.8 . . C22 C14 H00I 108.8 . . H00G C14 H00I 107.7 . . C26 C15 C8 120.0(2) . . C26 C15 H00J 120.0 . . C8 C15 H00J 120.0 . . C5 C16 C26 118.04(19) . . C5 C16 C25 123.06(19) . . C26 C16 C25 118.87(19) . . N2 C17 C9 102.81(15) . . N2 C17 H00K 111.2 . . C9 C17 H00K 111.2 . . N2 C17 H00L 111.2 . . C9 C17 H00L 111.2 . . H00K C17 H00L 109.1 . . C11 C18 H00M 109.5 . . C11 C18 H00N 109.5 . . H00M C18 H00N 109.5 . . C11 C18 H00O 109.5 . . H00M C18 H00O 109.5 . . H00N C18 H00O 109.5 . . C4 C19 C21 117.0(2) . . C4 C19 H00P 121.5 . . C21 C19 H00P 121.5 . . C29 C20 C7 116.7(2) . . C29 C20 H00Q 108.1 . . C7 C20 H00Q 108.1 . . C29 C20 H00R 108.1 . . C7 C20 H00R 108.1 . . H00Q C20 H00R 107.3 . . C13 C21 C19 121.0(2) . . C13 C21 H00S 119.5 . . C19 C21 H00S 119.5 . . C14 C22 H00T 109.5 . . C14 C22 H00U 109.5 . . H00T C22 H00U 109.5 . . C14 C22 H00V 109.5 . . H00T C22 H00V 109.5 . . H00U C22 H00V 109.5 . . C27 C23 C12 120.8(2) . . C27 C23 H00W 119.6 . . C12 C23 H00W 119.6 . . C27 C24 C6 121.8(2) . . C27 C24 H00X 119.1 . . C6 C24 H00X 119.1 . . C16 C25 C28 113.88(19) . . C16 C25 H00Y 108.8 . . C28 C25 H00Y 108.8 . . C16 C25 H00Z 108.8 . . C28 C25 H00Z 108.8 . . H00Y C25 H00Z 107.7 . . C15 C26 C16 121.1(2) . . C15 C26 H010 119.4 . . C16 C26 H010 119.4 . . C23 C27 C24 119.9(2) . . C23 C27 H011 120.1 . . C24 C27 H011 120.1 . . C25 C28 H012 109.5 . . C25 C28 H013 109.5 . . H012 C28 H013 109.5 . . C25 C28 H014 109.5 . . H012 C28 H014 109.5 . . H013 C28 H014 109.5 . . C20 C29 H015 109.5 . . C20 C29 H016 109.5 . . H015 C29 H016 109.5 . . C20 C29 H017 109.5 . . H015 C29 H017 109.5 . . H016 C29 H017 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C1 1.372(2) . O1 B1 1.427(3) . B1 O2 1.432(3) . B1 B2 1.650(3) . O2 C4 1.374(2) . B2 C3 1.580(3) . B2 B2 1.605(5) 2_666 N1 C3 1.346(2) . N1 C2 1.446(2) . N1 C9 1.473(2) . N2 C3 1.353(2) . N2 C5 1.446(2) . N2 C17 1.473(2) . C1 C10 1.380(3) . C1 C4 1.382(3) . C2 C6 1.401(3) . C2 C12 1.402(3) . C4 C19 1.373(3) . C5 C16 1.393(3) . C5 C7 1.409(3) . C6 C24 1.395(3) . C6 C11 1.506(3) . C7 C8 1.393(3) . C7 C20 1.509(3) . C8 C15 1.383(3) . C8 H00C 0.9500 . C9 C17 1.518(3) . C9 H00A 0.9900 . C9 H00B 0.9900 . C10 C13 1.391(3) . C10 H00E 0.9500 . C11 C18 1.525(3) . C11 H00D 0.9900 . C11 H00F 0.9900 . C12 C23 1.393(3) . C12 C14 1.513(3) . C13 C21 1.384(3) . C13 H00H 0.9500 . C14 C22 1.530(3) . C14 H00G 0.9900 . C14 H00I 0.9900 . C15 C26 1.377(3) . C15 H00J 0.9500 . C16 C26 1.402(3) . C16 C25 1.513(3) . C17 H00K 0.9900 . C17 H00L 0.9900 . C18 H00M 0.9800 . C18 H00N 0.9800 . C18 H00O 0.9800 . C19 C21 1.398(3) . C19 H00P 0.9500 . C20 C29 1.504(3) . C20 H00Q 0.9900 . C20 H00R 0.9900 . C21 H00S 0.9500 . C22 H00T 0.9800 . C22 H00U 0.9800 . C22 H00V 0.9800 . C23 C27 1.380(3) . C23 H00W 0.9500 . C24 C27 1.381(3) . C24 H00X 0.9500 . C25 C28 1.519(3) . C25 H00Y 0.9900 . C25 H00Z 0.9900 . C26 H010 0.9500 . C27 H011 0.9500 . C28 H012 0.9800 . C28 H013 0.9800 . C28 H014 0.9800 . C29 H015 0.9800 . C29 H016 0.9800 . C29 H017 0.9800 .