#------------------------------------------------------------------------------ #$Date: 2020-07-06 04:44:48 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253776 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126538.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_7126538 loop_ _publ_author_name 'Chen, Yu' 'Quan, Yangjian' 'Xie, Zuowei' _publ_section_title ; Ir-catalyzed selective dehydrogenative cross-coupling of aryls with o-carboranes via a mixed directing-group strategy. ; _journal_issue 51 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 7001 _journal_page_last 7004 _journal_paper_doi 10.1039/d0cc02531c _journal_volume 56 _journal_year 2020 _chemical_formula_sum 'C12 H20 B10 N2' _chemical_formula_weight 300.40 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/6 _audit_update_record ; 2020-03-02 deposited with the CCDC. 2020-05-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.491(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 19.063(3) _cell_length_b 6.8433(9) _cell_length_c 13.5027(18) _cell_measurement_reflns_used 210 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 15 _cell_measurement_theta_min 15 _cell_volume 1759.8(4) _computing_cell_refinement 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_data_collection 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_data_reduction 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'BRUKER SHELXTL' _computing_structure_refinement 'SHELXL-2014/6 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'BRUKER KAPPA APEXII DUO DIFFRACTOMETER' _diffrn_measurement_method 'PHI & OMEGA SCAN' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0608 _diffrn_reflns_av_unetI/netI 0.0379 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 26871 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.249 _diffrn_reflns_theta_min 1.069 _exptl_absorpt_coefficient_mu 0.058 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6800 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.134 _exptl_crystal_description block _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.220 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 3188 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.024 _refine_ls_R_factor_all 0.1191 _refine_ls_R_factor_gt 0.0653 _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^)+(0.1251P)^2^+0.6397P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1917 _refine_ls_wR_factor_ref 0.2419 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1844 _reflns_number_total 3188 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc02531c2.cif _cod_data_source_block 3as _cod_depositor_comments 'Adding full bibliography for 7126537--7126543.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7126538 _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_min 0.977 _shelx_estimated_absorpt_t_max 0.988 _shelxl_version_number 2014/6 _shelx_res_file ; TITL P in P2(1)/c CELL 0.71073 19.06320 6.84330 13.50270 90.0000 92.4906 90.0000 ZERR 4.00 0.00250 0.00090 0.00180 0.0000 0.0091 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H B N UNIT 48 80 40 8 OMIT -3 50.5 REM C12 H20 B10 N2 REM APEXII BLOCK COLOURLESS L.S. 4 ACTA FMAP 2 PLAN 20 SIZE 0.40 0.3 0.20 TEMP 23.000 WGHT 0.125100 0.639700 FVAR 0.16468 N1 4 0.360677 0.355142 0.752396 11.00000 0.04078 0.08455 = 0.06443 0.00076 -0.00375 0.00099 N2 4 0.346057 0.404958 0.846138 11.00000 0.06492 0.12777 = 0.06744 0.00028 0.00510 0.00290 C1 1 0.200831 0.406159 0.709276 11.00000 0.04372 0.08537 = 0.10351 0.02315 0.00413 0.00507 AFIX 153 H1 2 0.234061 0.297361 0.748722 11.00000 -1.20000 AFIX 0 C2 1 0.129483 0.494902 0.757277 11.00000 0.04387 0.08537 = 0.07553 0.01457 0.01078 0.00077 C11 1 0.112188 0.424186 0.860730 11.00000 0.07645 0.21524 = 0.10012 0.06214 0.02598 -0.00255 AFIX 33 H11A 2 0.069766 0.485743 0.880516 11.00000 -1.50000 H11B 2 0.105917 0.284998 0.859747 11.00000 -1.50000 H11C 2 0.150012 0.457384 0.906929 11.00000 -1.50000 AFIX 0 C12 1 0.323437 0.601712 0.628916 11.00000 0.04305 0.05911 = 0.05396 -0.00801 0.00614 -0.00454 C13 1 0.345693 0.736848 0.559127 11.00000 0.05453 0.07654 = 0.07605 0.00151 0.00960 -0.00522 AFIX 43 H13A 2 0.311990 0.807821 0.522560 11.00000 -1.20000 AFIX 0 C14 1 0.416133 0.769238 0.542275 11.00000 0.06526 0.10013 = 0.09269 0.01253 0.02126 -0.01525 AFIX 43 H14A 2 0.428909 0.858877 0.494528 11.00000 -1.20000 AFIX 0 C15 1 0.466391 0.668920 0.596104 11.00000 0.04427 0.13072 = 0.10824 0.00273 0.01601 -0.01801 AFIX 43 H15A 2 0.513679 0.691784 0.586324 11.00000 -1.20000 AFIX 0 C16 1 0.446862 0.534233 0.664688 11.00000 0.04246 0.11316 = 0.09498 0.00862 0.00504 -0.00365 AFIX 43 H16A 2 0.481002 0.464096 0.700863 11.00000 -1.20000 AFIX 0 C17 1 0.376765 0.502167 0.680338 11.00000 0.04143 0.07440 = 0.06009 -0.00866 0.00470 -0.00559 C18 1 0.361007 0.160800 0.740358 11.00000 0.07642 0.07925 = 0.10142 0.00331 -0.00737 -0.00108 AFIX 43 H18A 2 0.370550 0.095010 0.682199 11.00000 -1.20000 AFIX 0 C19 1 0.345154 0.076869 0.826884 11.00000 0.07737 0.10884 = 0.14179 0.04468 -0.01915 -0.01233 AFIX 43 H19A 2 0.340886 -0.055667 0.840611 11.00000 -1.20000 AFIX 0 C20 1 0.336746 0.231101 0.890074 11.00000 0.06057 0.15763 = 0.09083 0.05293 -0.00110 -0.00975 AFIX 43 H20A 2 0.325793 0.217013 0.956142 11.00000 -1.20000 AFIX 0 B3 3 0.201002 0.633849 0.748401 11.00000 0.04115 0.09181 = 0.06164 -0.01012 0.01228 -0.00385 AFIX 153 H3 2 0.233658 0.679979 0.813400 11.00000 -1.20000 AFIX 0 B4 3 0.241674 0.579205 0.639539 11.00000 0.04167 0.05310 = 0.05304 -0.00482 0.00451 0.00095 B5 3 0.188656 0.390158 0.586143 11.00000 0.05129 0.09390 = 0.10269 -0.05246 0.01226 -0.00622 AFIX 153 H5 2 0.211967 0.275297 0.541025 11.00000 -1.20000 AFIX 0 B6 3 0.119247 0.337331 0.663109 11.00000 0.04660 0.05882 = 0.15393 -0.02909 0.01850 -0.00765 AFIX 153 H6 2 0.097515 0.189135 0.669250 11.00000 -1.20000 AFIX 0 B7 3 0.118525 0.730159 0.728422 11.00000 0.05704 0.06252 = 0.11024 -0.01904 0.02127 0.00152 AFIX 153 H7 2 0.096027 0.839301 0.777736 11.00000 -1.20000 AFIX 0 B8 3 0.187244 0.785518 0.651254 11.00000 0.05777 0.04892 = 0.15165 0.00923 0.02920 0.00775 AFIX 153 H8 2 0.209685 0.933374 0.648206 11.00000 -1.20000 AFIX 0 B9 3 0.177625 0.632695 0.545794 11.00000 0.04616 0.18623 = 0.06315 0.03818 0.00361 0.01100 AFIX 153 H9 2 0.192965 0.678743 0.471743 11.00000 -1.20000 AFIX 0 B10 3 0.103633 0.487403 0.559414 11.00000 0.04274 0.21181 = 0.07669 -0.04881 -0.00454 -0.00804 AFIX 153 H10 2 0.071139 0.439241 0.494649 11.00000 -1.20000 AFIX 0 B11 3 0.066324 0.545936 0.671073 11.00000 0.04115 0.07556 = 0.07828 -0.00426 0.00079 0.00432 AFIX 153 H11 2 0.009497 0.534330 0.680914 11.00000 -1.20000 AFIX 0 B12 3 0.102934 0.733479 0.601875 11.00000 0.05384 0.10774 = 0.11788 0.04571 0.00869 0.02496 AFIX 153 H12 2 0.070144 0.847786 0.566077 11.00000 -1.20000 AFIX 0 HKLF 4 REM P in P2(1)/c REM R1 = 0.0653 for 1844 Fo > 4sig(Fo) and 0.1191 for all 3188 data REM 217 parameters refined using 0 restraints END WGHT 0.1252 0.6364 REM Highest difference peak 0.220, deepest hole -0.185, 1-sigma level 0.038 Q1 1 0.2123 0.5665 0.7213 11.00000 0.05 0.22 Q2 1 0.1105 0.1908 0.7291 11.00000 0.05 0.18 Q3 1 0.1784 0.7190 0.7231 11.00000 0.05 0.17 Q4 1 0.2210 0.6295 0.7628 11.00000 0.05 0.17 Q5 1 0.0269 0.5259 0.7233 11.00000 0.05 0.17 Q6 1 0.0892 0.7342 0.6714 11.00000 0.05 0.16 Q7 1 0.1327 0.4018 0.5988 11.00000 0.05 0.16 Q8 1 0.0998 0.5799 0.8474 11.00000 0.05 0.15 Q9 1 0.1583 0.7477 0.6002 11.00000 0.05 0.15 Q10 1 0.1233 0.2881 0.7966 11.00000 0.05 0.15 Q11 1 0.1931 0.6495 0.5349 11.00000 0.05 0.14 Q12 1 0.1094 0.7714 0.8306 11.00000 0.05 0.14 Q13 1 0.1985 0.5058 0.5522 11.00000 0.05 0.14 Q14 1 0.0842 0.6431 0.5596 11.00000 0.05 0.13 Q15 1 0.0565 0.3291 0.8430 11.00000 0.05 0.13 Q16 1 0.2109 0.6354 0.5732 11.00000 0.05 0.13 Q17 1 0.0980 0.5783 0.7252 11.00000 0.05 0.13 Q18 1 0.0872 0.3374 0.5241 11.00000 0.05 0.13 Q19 1 0.2313 0.2409 0.5910 11.00000 0.05 0.13 Q20 1 0.1178 0.6060 0.7393 11.00000 0.05 0.12 ; _shelx_res_checksum 67518 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.36068(12) 0.3551(4) 0.75240(19) 0.0634(7) Uani 1 1 d . . . . . N2 N 0.34606(14) 0.4050(5) 0.8461(2) 0.0866(9) Uani 1 1 d . . . . . C1 C 0.20083(16) 0.4062(5) 0.7093(3) 0.0775(10) Uani 1 1 d . . . . . H1 H 0.2341 0.2974 0.7487 0.093 Uiso 1 1 calc R U . . . C2 C 0.12948(15) 0.4949(5) 0.7573(2) 0.0680(9) Uani 1 1 d . . . . . C11 C 0.1122(2) 0.4242(8) 0.8607(3) 0.1300(19) Uani 1 1 d . . . . . H11A H 0.0698 0.4857 0.8805 0.195 Uiso 1 1 calc R U . . . H11B H 0.1059 0.2850 0.8597 0.195 Uiso 1 1 calc R U . . . H11C H 0.1500 0.4574 0.9069 0.195 Uiso 1 1 calc R U . . . C12 C 0.32344(14) 0.6017(4) 0.6289(2) 0.0519(7) Uani 1 1 d . . . . . C13 C 0.34569(16) 0.7368(4) 0.5591(2) 0.0688(9) Uani 1 1 d . . . . . H13A H 0.3120 0.8078 0.5226 0.083 Uiso 1 1 calc R U . . . C14 C 0.41613(19) 0.7692(5) 0.5423(3) 0.0855(11) Uani 1 1 d . . . . . H14A H 0.4289 0.8589 0.4945 0.103 Uiso 1 1 calc R U . . . C15 C 0.46639(19) 0.6689(6) 0.5961(3) 0.0940(12) Uani 1 1 d . . . . . H15A H 0.5137 0.6918 0.5863 0.113 Uiso 1 1 calc R U . . . C16 C 0.44686(16) 0.5342(6) 0.6647(3) 0.0835(11) Uani 1 1 d . . . . . H16A H 0.4810 0.4641 0.7009 0.100 Uiso 1 1 calc R U . . . C17 C 0.37676(14) 0.5022(4) 0.6803(2) 0.0586(8) Uani 1 1 d . . . . . C18 C 0.36101(19) 0.1608(5) 0.7404(3) 0.0860(11) Uani 1 1 d . . . . . H18A H 0.3705 0.0950 0.6822 0.103 Uiso 1 1 calc R U . . . C19 C 0.3452(2) 0.0769(7) 0.8269(4) 0.1100(15) Uani 1 1 d . . . . . H19A H 0.3409 -0.0557 0.8406 0.132 Uiso 1 1 calc R U . . . C20 C 0.3367(2) 0.2311(9) 0.8901(3) 0.1031(15) Uani 1 1 d . . . . . H20A H 0.3258 0.2170 0.9561 0.124 Uiso 1 1 calc R U . . . B3 B 0.20100(18) 0.6338(5) 0.7484(3) 0.0646(10) Uani 1 1 d . . . . . H3 H 0.2337 0.6800 0.8134 0.077 Uiso 1 1 calc R U . . . B4 B 0.24167(16) 0.5792(4) 0.6395(2) 0.0492(8) Uani 1 1 d . . . . . B5 B 0.1887(2) 0.3902(6) 0.5861(3) 0.0824(13) Uani 1 1 d . . . . . H5 H 0.2120 0.2753 0.5410 0.099 Uiso 1 1 calc R U . . . B6 B 0.1192(2) 0.3373(6) 0.6631(4) 0.0860(14) Uani 1 1 d . . . . . H6 H 0.0975 0.1891 0.6693 0.103 Uiso 1 1 calc R U . . . B7 B 0.1185(2) 0.7302(5) 0.7284(3) 0.0761(12) Uani 1 1 d . . . . . H7 H 0.0960 0.8393 0.7777 0.091 Uiso 1 1 calc R U . . . B8 B 0.1872(2) 0.7855(5) 0.6513(4) 0.0854(14) Uani 1 1 d . . . . . H8 H 0.2097 0.9334 0.6482 0.102 Uiso 1 1 calc R U . . . B9 B 0.1776(2) 0.6327(8) 0.5458(3) 0.0985(17) Uani 1 1 d . . . . . H9 H 0.1930 0.6787 0.4717 0.118 Uiso 1 1 calc R U . . . B10 B 0.1036(2) 0.4874(10) 0.5594(4) 0.1106(19) Uani 1 1 d . . . . . H10 H 0.0711 0.4392 0.4946 0.133 Uiso 1 1 calc R U . . . B11 B 0.06632(18) 0.5459(5) 0.6711(3) 0.0651(10) Uani 1 1 d . . . . . H11 H 0.0095 0.5343 0.6809 0.078 Uiso 1 1 calc R U . . . B12 B 0.1029(2) 0.7335(7) 0.6019(4) 0.0930(15) Uani 1 1 d . . . . . H12 H 0.0701 0.8478 0.5661 0.112 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 N1 0.0408(14) 0.0846(18) 0.0644(17) 0.0008(14) -0.0037(11) 0.0010(12) N2 0.065(2) 0.128(3) 0.0674(19) 0.0003(19) 0.0051(14) 0.0029(17) C1 0.0437(18) 0.085(2) 0.104(3) 0.023(2) 0.0041(17) 0.0051(15) C2 0.0439(17) 0.085(2) 0.076(2) 0.0146(17) 0.0108(15) 0.0008(15) C11 0.076(3) 0.215(5) 0.100(3) 0.062(3) 0.026(2) -0.003(3) C12 0.0430(16) 0.0591(15) 0.0540(16) -0.0080(13) 0.0061(13) -0.0045(12) C13 0.055(2) 0.077(2) 0.076(2) 0.0015(17) 0.0096(16) -0.0052(15) C14 0.065(2) 0.100(3) 0.093(3) 0.013(2) 0.021(2) -0.015(2) C15 0.044(2) 0.131(3) 0.108(3) 0.003(3) 0.016(2) -0.018(2) C16 0.0425(19) 0.113(3) 0.095(3) 0.009(2) 0.0050(17) -0.0036(18) C17 0.0414(17) 0.0744(18) 0.0601(18) -0.0087(15) 0.0047(13) -0.0056(14) C18 0.076(3) 0.079(2) 0.101(3) 0.003(2) -0.007(2) -0.0011(19) C19 0.077(3) 0.109(3) 0.142(4) 0.045(3) -0.019(3) -0.012(2) C20 0.061(2) 0.158(4) 0.091(3) 0.053(3) -0.001(2) -0.010(3) B3 0.0412(19) 0.092(3) 0.062(2) -0.0101(19) 0.0123(16) -0.0039(17) B4 0.0417(18) 0.0531(16) 0.0530(19) -0.0048(14) 0.0045(14) 0.0010(13) B5 0.051(2) 0.094(3) 0.103(3) -0.052(3) 0.012(2) -0.0062(19) B6 0.047(2) 0.059(2) 0.154(4) -0.029(2) 0.018(2) -0.0076(17) B7 0.057(2) 0.063(2) 0.110(3) -0.019(2) 0.021(2) 0.0015(17) B8 0.058(2) 0.0489(19) 0.152(4) 0.009(2) 0.029(3) 0.0077(16) B9 0.046(2) 0.186(5) 0.063(2) 0.038(3) 0.0036(18) 0.011(3) B10 0.043(2) 0.212(6) 0.077(3) -0.049(3) -0.0045(19) -0.008(3) B11 0.0412(19) 0.076(2) 0.078(2) -0.0043(18) 0.0008(17) 0.0043(16) B12 0.054(2) 0.108(3) 0.118(4) 0.046(3) 0.009(2) 0.025(2) 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' 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 C18 N1 N2 111.5(3) . . ? C18 N1 C17 127.5(3) . . ? N2 N1 C17 121.0(3) . . ? C20 N2 N1 103.1(3) . . ? B3 C1 C2 61.0(2) . . ? B3 C1 B5 112.3(3) . . ? C2 C1 B5 109.5(3) . . ? B3 C1 B6 111.5(3) . . ? C2 C1 B6 59.6(2) . . ? B5 C1 B6 62.4(3) . . ? B3 C1 B4 61.91(19) . . ? C2 C1 B4 111.3(2) . . ? B5 C1 B4 63.1(2) . . ? B6 C1 B4 114.5(3) . . ? C11 C2 C1 117.2(3) . . ? C11 C2 B7 119.3(3) . . ? C1 C2 B7 111.2(2) . . ? C11 C2 B3 117.1(3) . . ? C1 C2 B3 59.43(18) . . ? B7 C2 B3 61.8(2) . . ? C11 C2 B6 117.9(3) . . ? C1 C2 B6 62.2(2) . . ? B7 C2 B6 115.8(3) . . ? B3 C2 B6 112.4(2) . . ? C11 C2 B11 121.6(3) . . ? C1 C2 B11 112.6(3) . . ? B7 C2 B11 63.7(2) . . ? B3 C2 B11 113.3(3) . . ? B6 C2 B11 63.2(2) . . ? C17 C12 C13 115.2(3) . . ? C17 C12 B4 127.8(3) . . ? C13 C12 B4 117.1(3) . . ? C14 C13 C12 122.6(3) . . ? C15 C14 C13 119.6(3) . . ? C14 C15 C16 119.6(3) . . ? C15 C16 C17 120.3(3) . . ? C16 C17 C12 122.7(3) . . ? C16 C17 N1 116.8(3) . . ? C12 C17 N1 120.6(2) . . ? N1 C18 C19 108.4(4) . . ? C18 C19 C20 104.4(4) . . ? N2 C20 C19 112.7(4) . . ? C1 B3 C2 59.6(2) . . ? C1 B3 B8 109.6(3) . . ? C2 B3 B8 107.9(3) . . ? C1 B3 B7 108.9(3) . . ? C2 B3 B7 59.0(2) . . ? B8 B3 B7 62.0(2) . . ? C1 B3 B4 61.17(19) . . ? C2 B3 B4 109.6(3) . . ? B8 B3 B4 62.1(2) . . ? B7 B3 B4 113.0(3) . . ? C12 B4 C1 126.1(2) . . ? C12 B4 B3 122.4(2) . . ? C1 B4 B3 56.92(19) . . ? C12 B4 B9 124.9(3) . . ? C1 B4 B9 102.7(3) . . ? B3 B4 B9 104.1(2) . . ? C12 B4 B8 121.1(2) . . ? C1 B4 B8 102.7(2) . . ? B3 B4 B8 57.6(2) . . ? B9 B4 B8 60.3(3) . . ? C12 B4 B5 125.5(2) . . ? C1 B4 B5 57.1(2) . . ? B3 B4 B5 103.5(2) . . ? B9 B4 B5 59.6(3) . . ? B8 B4 B5 107.0(3) . . ? C1 B5 B6 60.0(2) . . ? C1 B5 B9 104.8(3) . . ? B6 B5 B9 107.2(3) . . ? C1 B5 B10 105.3(3) . . ? B6 B5 B10 59.5(3) . . ? B9 B5 B10 59.1(3) . . ? C1 B5 B4 59.8(2) . . ? B6 B5 B4 109.9(3) . . ? B9 B5 B4 59.7(2) . . ? B10 B5 B4 107.9(3) . . ? C2 B6 C1 58.2(2) . . ? C2 B6 B10 103.9(3) . . ? C1 B6 B10 104.4(3) . . ? C2 B6 B11 58.5(2) . . ? C1 B6 B11 105.6(3) . . ? B10 B6 B11 59.6(3) . . ? C2 B6 B5 104.6(2) . . ? C1 B6 B5 57.6(2) . . ? B10 B6 B5 60.8(3) . . ? B11 B6 B5 108.6(3) . . ? C2 B7 B3 59.2(2) . . ? C2 B7 B12 105.0(3) . . ? B3 B7 B12 106.2(3) . . ? C2 B7 B8 105.0(2) . . ? B3 B7 B8 58.1(2) . . ? B12 B7 B8 60.5(3) . . ? C2 B7 B11 58.3(2) . . ? B3 B7 B11 106.9(2) . . ? B12 B7 B11 60.3(2) . . ? B8 B7 B11 108.4(3) . . ? B3 B8 B12 106.3(3) . . ? B3 B8 B7 59.9(2) . . ? B12 B8 B7 58.9(3) . . ? B3 B8 B4 60.3(2) . . ? B12 B8 B4 109.7(3) . . ? B7 B8 B4 109.8(3) . . ? B3 B8 B9 105.6(3) . . ? B12 B8 B9 60.8(3) . . ? B7 B8 B9 107.3(3) . . ? B4 B8 B9 59.7(2) . . ? B10 B9 B5 61.0(3) . . ? B10 B9 B4 110.2(3) . . ? B5 B9 B4 60.7(2) . . ? B10 B9 B8 108.0(3) . . ? B5 B9 B8 107.6(3) . . ? B4 B9 B8 60.0(2) . . ? B10 B9 B12 60.7(3) . . ? B5 B9 B12 108.7(3) . . ? B4 B9 B12 108.5(3) . . ? B8 B9 B12 59.1(3) . . ? B11 B10 B9 108.9(3) . . ? B11 B10 B6 60.3(2) . . ? B9 B10 B6 108.0(3) . . ? B11 B10 B5 108.3(3) . . ? B9 B10 B5 59.9(2) . . ? B6 B10 B5 59.7(3) . . ? B11 B10 B12 59.6(2) . . ? B9 B10 B12 60.7(3) . . ? B6 B10 B12 107.5(3) . . ? B5 B10 B12 108.0(3) . . ? C2 B11 B10 104.2(3) . . ? C2 B11 B12 103.5(3) . . ? B10 B11 B12 61.3(3) . . ? C2 B11 B6 58.3(2) . . ? B10 B11 B6 60.1(3) . . ? B12 B11 B6 108.7(3) . . ? C2 B11 B7 57.9(2) . . ? B10 B11 B7 107.5(3) . . ? B12 B11 B7 58.7(3) . . ? B6 B11 B7 107.1(3) . . ? B7 B12 B8 60.6(3) . . ? B7 B12 B11 61.1(2) . . ? B8 B12 B11 109.1(3) . . ? B7 B12 B10 107.7(3) . . ? B8 B12 B10 107.2(3) . . ? B11 B12 B10 59.1(2) . . ? B7 B12 B9 108.1(3) . . ? B8 B12 B9 60.2(2) . . ? B11 B12 B9 106.7(3) . . ? B10 B12 B9 58.6(3) . . ? 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 C18 1.340(4) . ? N1 N2 1.352(3) . ? N1 C17 1.442(4) . ? N2 C20 1.345(5) . ? C1 B3 1.645(5) . ? C1 C2 1.648(4) . ? C1 B5 1.672(6) . ? C1 B6 1.716(5) . ? C1 B4 1.720(4) . ? C2 C11 1.528(5) . ? C2 B7 1.667(5) . ? C2 B3 1.671(5) . ? C2 B6 1.672(5) . ? C2 B11 1.675(5) . ? C12 C17 1.385(4) . ? C12 C13 1.399(4) . ? C12 B4 1.579(4) . ? C13 C14 1.389(4) . ? C14 C15 1.363(5) . ? C15 C16 1.370(5) . ? C16 C17 1.379(4) . ? C18 C19 1.348(5) . ? C19 C20 1.371(6) . ? B3 B8 1.684(6) . ? B3 B7 1.715(5) . ? B3 B4 1.732(4) . ? B4 B9 1.759(5) . ? B4 B8 1.763(5) . ? B4 B5 1.775(5) . ? B5 B6 1.755(6) . ? B5 B9 1.757(7) . ? B5 B10 1.775(6) . ? B6 B10 1.751(7) . ? B6 B11 1.754(5) . ? B7 B12 1.722(7) . ? B7 B8 1.750(6) . ? B7 B11 1.764(5) . ? B8 B12 1.750(7) . ? B8 B9 1.770(7) . ? B9 B10 1.742(7) . ? B9 B12 1.780(6) . ? B10 B11 1.741(6) . ? B10 B12 1.779(8) . ? B11 B12 1.750(6) . ?