#------------------------------------------------------------------------------ #$Date: 2020-07-06 04:44:48 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253776 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126541.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_7126541 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 'C13 H20 B10 N2' _chemical_formula_weight 312.41 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-03-02 deposited with the CCDC. 2020-05-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.3782(12) _cell_length_b 11.4876(11) _cell_length_c 13.5646(15) _cell_measurement_reflns_used 349 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 15 _cell_measurement_theta_min 15 _cell_volume 1773.0(3) _computing_cell_refinement 'BRUKER D8VENTURE DIFFRACTOMETER' _computing_data_collection 'BRUKER D8VENTURE DIFFRACTOMETER' _computing_data_reduction 'BRUKER D8VENTURE DIFFRACTOMETER' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'BRUKER SHELXTL' _computing_structure_refinement 'SHELXL-2014/6 (Sheldrick, 2014)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'BRUKER D8VENTURE DIFFRACTOMETER' _diffrn_measurement_method 'PHI & OMEGA SCAN' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1414 _diffrn_reflns_av_unetI/netI 0.0491 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 67985 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.233 _diffrn_reflns_theta_max 25.233 _diffrn_reflns_theta_min 2.323 _exptl_absorpt_coefficient_mu 0.060 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.5181 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.170 _exptl_crystal_description block _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.558 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.058 _refine_ls_abs_structure_details ; Flack x determined using 774 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -5.4(10) _refine_ls_extinction_coef 0.030(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 3218 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.1113 _refine_ls_R_factor_gt 0.0826 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1321P)^2^+0.8621P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2131 _refine_ls_wR_factor_ref 0.2336 _reflns_Friedel_coverage 0.741 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 2380 _reflns_number_total 3218 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc02531c2.cif _cod_data_source_block 3aq _cod_depositor_comments 'Adding full bibliography for 7126537--7126543.cif.' _cod_database_code 7126541 _shelx_shelxl_version_number 2018/3 _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_min 0.976 _shelx_estimated_absorpt_t_max 0.988 _shelx_res_file ; TITL P in P2(1)2(1)2(1) p.res created by SHELXL-2018/3 at 11:58:33 on 20-Aug-2019 CELL 0.71073 11.37820 11.48760 13.56460 90.0000 90.0000 90.0000 ZERR 4.00 0.00120 0.00110 0.00150 0.0000 0.0000 0.0000 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 UNIT 52 80 40 8 REM C13 H20 B10 N2 REM D8VENTURE BLOCK COLOURLESS OMIT -3 50.5 SIZE 0.40 0.30 0.20 L.S. 4 ACTA FMAP 2 PLAN 20 TEMP 24.690 WGHT 0.132100 0.862100 EXTI 0.030198 FVAR 0.28325 N1 4 0.468481 0.914153 0.195099 11.00000 0.05137 0.04025 = 0.06812 -0.00652 0.00257 -0.00655 N2 4 0.576369 0.737932 0.203570 11.00000 0.05154 0.05397 = 0.06367 0.00196 -0.00546 -0.00182 C1 1 0.237668 0.912278 0.303658 11.00000 0.09851 0.07110 = 0.09122 -0.02835 0.02629 -0.02092 AFIX 153 H1 2 0.300077 0.967917 0.263466 11.00000 -1.20000 AFIX 0 C2 1 0.226500 0.918780 0.419260 11.00000 0.12308 0.09449 = 0.08249 -0.03845 0.03447 -0.03529 C11 1 0.309710 1.003716 0.472650 11.00000 0.14691 0.19433 = 0.15712 -0.10480 0.00737 -0.05226 AFIX 33 H11A 2 0.370473 0.960558 0.505437 11.00000 -1.50000 H11B 2 0.344438 1.055659 0.425480 11.00000 -1.50000 H11C 2 0.266074 1.047864 0.520307 11.00000 -1.50000 AFIX 0 C12 1 0.271381 0.735240 0.152801 11.00000 0.04607 0.03378 = 0.04353 0.00218 -0.00959 -0.00267 C13 1 0.193070 0.672418 0.090168 11.00000 0.04483 0.06171 = 0.05685 0.00183 -0.01632 -0.00640 AFIX 43 H13A 2 0.114391 0.666028 0.107937 11.00000 -1.20000 AFIX 0 C14 1 0.230688 0.621286 0.004591 11.00000 0.07524 0.06496 = 0.05646 -0.01687 -0.01401 -0.01870 AFIX 43 H14A 2 0.176647 0.583024 -0.035357 11.00000 -1.20000 AFIX 0 C15 1 0.345850 0.625349 -0.023237 11.00000 0.08220 0.07513 = 0.05581 -0.01936 0.00571 -0.01766 AFIX 43 H15A 2 0.370849 0.588945 -0.080774 11.00000 -1.20000 AFIX 0 C16 1 0.424070 0.684325 0.035501 11.00000 0.05553 0.06236 = 0.05163 -0.00893 0.00665 -0.01200 AFIX 43 H16A 2 0.502723 0.687246 0.017017 11.00000 -1.20000 AFIX 0 C17 1 0.388913 0.740246 0.122476 11.00000 0.04497 0.03532 = 0.03945 0.00400 -0.00031 -0.00177 C18 1 0.483504 0.800981 0.179149 11.00000 0.04660 0.03654 = 0.03754 0.00179 0.00835 -0.00973 C19 1 0.556100 0.966868 0.244266 11.00000 0.06459 0.04936 = 0.07723 -0.01892 0.01000 -0.01632 AFIX 43 H19A 2 0.549820 1.046070 0.257450 11.00000 -1.20000 AFIX 0 C20 1 0.653574 0.909194 0.275544 11.00000 0.06291 0.08294 = 0.06279 -0.01598 -0.00274 -0.02503 AFIX 43 H20A 2 0.712619 0.946643 0.310783 11.00000 -1.20000 AFIX 0 C21 1 0.660508 0.794687 0.252918 11.00000 0.04992 0.07490 = 0.06960 0.00367 -0.01354 -0.00520 AFIX 43 H21A 2 0.726861 0.753515 0.272590 11.00000 -1.20000 AFIX 0 B3 3 0.123164 0.973275 0.362388 11.00000 0.10232 0.12407 = 0.16517 -0.08209 0.03042 -0.00236 AFIX 153 H3 2 0.104381 1.067172 0.364541 11.00000 -1.20000 AFIX 0 B4 3 0.108081 0.890951 0.257221 11.00000 0.09959 0.13103 = 0.09692 -0.01523 0.00133 0.06809 AFIX 153 H4 2 0.077657 0.930626 0.187969 11.00000 -1.20000 AFIX 0 B5 3 0.215133 0.778372 0.251976 11.00000 0.03780 0.04351 = 0.05056 -0.00235 -0.00279 0.00078 B6 3 0.294316 0.805112 0.360960 11.00000 0.05717 0.13754 = 0.04604 -0.01828 0.00887 -0.01664 AFIX 153 H6 2 0.389263 0.787251 0.363037 11.00000 -1.20000 AFIX 0 B7 3 0.093590 0.879000 0.465266 11.00000 0.07952 0.13988 = 0.08558 -0.03290 0.03143 -0.00392 AFIX 153 H7 2 0.051386 0.904595 0.534930 11.00000 -1.20000 AFIX 0 B8 3 0.016013 0.872567 0.356699 11.00000 0.05638 0.22874 = 0.13797 -0.08328 0.00817 0.04823 AFIX 153 H8 2 -0.076722 0.899468 0.354209 11.00000 -1.20000 AFIX 0 B9 3 0.068303 0.753962 0.289603 11.00000 0.05632 0.19896 = 0.15227 -0.11415 0.04666 -0.06486 AFIX 153 H9 2 0.007383 0.702715 0.243981 11.00000 -1.20000 AFIX 0 B10 3 0.193210 0.693662 0.358529 11.00000 0.17062 0.05793 = 0.10196 0.02510 0.07780 0.02434 AFIX 153 H10 2 0.217264 0.600918 0.358718 11.00000 -1.20000 AFIX 0 B11 3 0.209801 0.786516 0.464244 11.00000 0.09751 0.15499 = 0.05328 0.00941 0.02779 0.02279 AFIX 153 H11 2 0.250038 0.758462 0.534048 11.00000 -1.20000 AFIX 0 B12 3 0.070552 0.740758 0.423414 11.00000 0.18083 0.11623 = 0.17027 -0.07158 0.13551 -0.07729 AFIX 153 H12 2 0.016665 0.676849 0.463458 11.00000 -1.20000 AFIX 0 HKLF 4 REM P in P2(1)2(1)2(1) REM wR2 = 0.233638, GooF = S = 1.03665, Restrained GooF = 1.03665 for all data REM R1 = 0.082562 for 2380 Fo > 4sig(Fo) and 0.111320 for all 3218 data REM 227 parameters refined using 0 restraints END WGHT 0.1316 0.8660 REM Highest difference peak 0.558, deepest hole -0.265, 1-sigma level 0.058 Q1 1 0.1711 1.0781 0.4173 11.00000 0.05 0.56 Q2 1 0.0421 0.7660 0.3484 11.00000 0.05 0.33 Q3 1 0.1072 0.6646 0.3125 11.00000 0.05 0.26 Q4 1 0.1593 0.7081 0.4291 11.00000 0.05 0.26 Q5 1 0.0847 0.8074 0.2581 11.00000 0.05 0.22 Q6 1 0.2512 0.7381 0.3661 11.00000 0.05 0.20 Q7 1 0.0647 0.7570 0.4516 11.00000 0.05 0.20 Q8 1 0.0635 0.7484 0.2469 11.00000 0.05 0.19 Q9 1 0.2609 0.8362 0.4413 11.00000 0.05 0.19 Q10 1 0.0414 0.6837 0.3831 11.00000 0.05 0.19 Q11 1 0.1576 0.9011 0.2975 11.00000 0.05 0.18 Q12 1 0.2180 0.6924 0.4807 11.00000 0.05 0.17 Q13 1 0.0533 0.9046 0.3837 11.00000 0.05 0.17 Q14 1 0.0278 0.5737 0.3577 11.00000 0.05 0.16 Q15 1 0.0784 0.5778 0.3336 11.00000 0.05 0.15 Q16 1 0.0923 0.6357 0.4980 11.00000 0.05 0.15 Q17 1 0.0309 0.9008 0.3027 11.00000 0.05 0.15 Q18 1 0.0494 0.5787 0.4116 11.00000 0.05 0.14 Q19 1 0.1628 0.6016 0.2675 11.00000 0.05 0.14 Q20 1 0.4314 0.6816 0.1215 11.00000 0.05 0.13 ; _shelx_res_checksum 87472 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' 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 0.4685(4) 0.9142(4) 0.1951(3) 0.0532(12) Uani 1 1 d . . . . . N2 N 0.5764(4) 0.7379(4) 0.2036(3) 0.0564(12) Uani 1 1 d . . . . . C1 C 0.2377(7) 0.9123(7) 0.3037(6) 0.087(2) Uani 1 1 d . . . . . H1 H 0.300077 0.967917 0.263466 0.104 Uiso 1 1 calc R U . . . C2 C 0.2265(9) 0.9188(8) 0.4193(6) 0.100(3) Uani 1 1 d . . . . . C11 C 0.3097(10) 1.0037(11) 0.4727(9) 0.166(6) Uani 1 1 d . . . . . H11A H 0.370473 0.960558 0.505437 0.249 Uiso 1 1 calc R U . . . H11B H 0.344438 1.055659 0.425480 0.249 Uiso 1 1 calc R U . . . H11C H 0.266074 1.047864 0.520307 0.249 Uiso 1 1 calc R U . . . C12 C 0.2714(4) 0.7352(4) 0.1528(3) 0.0411(11) Uani 1 1 d . . . . . C13 C 0.1931(5) 0.6724(5) 0.0902(4) 0.0545(15) Uani 1 1 d . . . . . H13A H 0.114391 0.666028 0.107937 0.065 Uiso 1 1 calc R U . . . C14 C 0.2307(6) 0.6213(5) 0.0046(4) 0.0656(17) Uani 1 1 d . . . . . H14A H 0.176647 0.583024 -0.035357 0.079 Uiso 1 1 calc R U . . . C15 C 0.3459(6) 0.6253(6) -0.0232(5) 0.0710(18) Uani 1 1 d . . . . . H15A H 0.370849 0.588945 -0.080774 0.085 Uiso 1 1 calc R U . . . C16 C 0.4241(5) 0.6843(5) 0.0355(4) 0.0565(15) Uani 1 1 d . . . . . H16A H 0.502723 0.687246 0.017017 0.068 Uiso 1 1 calc R U . . . C17 C 0.3889(4) 0.7402(4) 0.1225(3) 0.0399(11) Uani 1 1 d . . . . . C18 C 0.4835(4) 0.8010(4) 0.1791(3) 0.0402(12) Uani 1 1 d . . . . . C19 C 0.5561(5) 0.9669(5) 0.2443(5) 0.0637(17) Uani 1 1 d . . . . . H19A H 0.549820 1.046070 0.257450 0.076 Uiso 1 1 calc R U . . . C20 C 0.6536(6) 0.9092(7) 0.2755(5) 0.0695(18) Uani 1 1 d . . . . . H20A H 0.712619 0.946643 0.310783 0.083 Uiso 1 1 calc R U . . . C21 C 0.6605(5) 0.7947(6) 0.2529(5) 0.0648(17) Uani 1 1 d . . . . . H21A H 0.726861 0.753515 0.272590 0.078 Uiso 1 1 calc R U . . . B3 B 0.1232(11) 0.9733(12) 0.3624(11) 0.131(5) Uani 1 1 d . . . . . H3 H 0.104381 1.067172 0.364541 0.157 Uiso 1 1 calc R U . . . B4 B 0.1081(9) 0.8910(10) 0.2572(8) 0.109(4) Uani 1 1 d . . . . . H4 H 0.077657 0.930626 0.187969 0.131 Uiso 1 1 calc R U . . . B5 B 0.2151(5) 0.7784(5) 0.2520(4) 0.0440(13) Uani 1 1 d . . . . . B6 B 0.2943(7) 0.8051(9) 0.3610(5) 0.080(3) Uani 1 1 d . . . . . H6 H 0.389263 0.787251 0.363037 0.096 Uiso 1 1 calc R U . . . B7 B 0.0936(8) 0.8790(11) 0.4653(8) 0.102(3) Uani 1 1 d . . . . . H7 H 0.051386 0.904595 0.534930 0.122 Uiso 1 1 calc R U . . . B8 B 0.0160(8) 0.8726(15) 0.3567(10) 0.141(6) Uani 1 1 d . . . . . H8 H -0.076722 0.899468 0.354209 0.169 Uiso 1 1 calc R U . . . B9 B 0.0683(8) 0.7540(13) 0.2896(9) 0.136(6) Uani 1 1 d . . . . . H9 H 0.007383 0.702715 0.243981 0.163 Uiso 1 1 calc R U . . . B10 B 0.1932(11) 0.6937(8) 0.3585(8) 0.110(4) Uani 1 1 d . . . . . H10 H 0.217264 0.600918 0.358718 0.132 Uiso 1 1 calc R U . . . B11 B 0.2098(9) 0.7865(11) 0.4642(7) 0.102(3) Uani 1 1 d . . . . . H11 H 0.250038 0.758462 0.534048 0.122 Uiso 1 1 calc R U . . . B12 B 0.0706(13) 0.7408(11) 0.4234(10) 0.156(7) Uani 1 1 d . . . . . H12 H 0.016665 0.676849 0.463458 0.187 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 0.051(3) 0.040(2) 0.068(3) -0.007(2) 0.003(2) -0.007(2) N2 0.052(3) 0.054(3) 0.064(3) 0.002(2) -0.005(2) -0.002(2) C1 0.099(6) 0.071(4) 0.091(5) -0.028(4) 0.026(5) -0.021(4) C2 0.123(7) 0.094(6) 0.082(5) -0.038(5) 0.034(5) -0.035(5) C11 0.147(10) 0.194(13) 0.157(10) -0.105(10) 0.007(8) -0.052(10) C12 0.046(3) 0.034(2) 0.044(3) 0.002(2) -0.010(2) -0.003(2) C13 0.045(3) 0.062(3) 0.057(3) 0.002(3) -0.016(2) -0.006(3) C14 0.075(4) 0.065(4) 0.056(4) -0.017(3) -0.014(3) -0.019(3) C15 0.082(5) 0.075(4) 0.056(4) -0.019(3) 0.006(3) -0.018(3) C16 0.056(3) 0.062(3) 0.052(3) -0.009(3) 0.007(3) -0.012(3) C17 0.045(2) 0.035(2) 0.039(3) 0.004(2) 0.000(2) -0.002(2) C18 0.047(3) 0.037(3) 0.038(2) 0.002(2) 0.008(2) -0.010(2) C19 0.065(4) 0.049(3) 0.077(4) -0.019(3) 0.010(3) -0.016(3) C20 0.063(4) 0.083(5) 0.063(4) -0.016(3) -0.003(3) -0.025(4) C21 0.050(3) 0.075(4) 0.070(4) 0.004(3) -0.014(3) -0.005(3) B3 0.102(8) 0.124(10) 0.165(11) -0.082(9) 0.030(9) -0.002(7) B4 0.100(7) 0.131(10) 0.097(7) -0.015(6) 0.001(6) 0.068(7) B5 0.038(3) 0.044(3) 0.051(3) -0.002(3) -0.003(3) 0.001(2) B6 0.057(4) 0.138(8) 0.046(4) -0.018(5) 0.009(3) -0.017(5) B7 0.080(6) 0.140(9) 0.086(6) -0.033(6) 0.031(5) -0.004(6) B8 0.056(5) 0.229(16) 0.138(9) -0.083(11) 0.008(6) 0.048(8) B9 0.056(5) 0.199(13) 0.152(10) -0.114(11) 0.047(6) -0.065(7) B10 0.171(10) 0.058(4) 0.102(7) 0.025(5) 0.078(8) 0.024(6) B11 0.098(7) 0.155(10) 0.053(4) 0.009(5) 0.028(5) 0.023(7) B12 0.181(13) 0.116(9) 0.170(11) -0.072(9) 0.136(11) -0.077(10) 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 C19 115.2(5) . . ? C18 N2 C21 115.5(5) . . ? C2 C1 B6 65.4(6) . . ? C2 C1 B4 108.7(7) . . ? B6 C1 B4 116.2(7) . . ? C2 C1 B3 56.3(7) . . ? B6 C1 B3 113.9(8) . . ? B4 C1 B3 62.8(6) . . ? C2 C1 B5 116.0(6) . . ? B6 C1 B5 64.2(4) . . ? B4 C1 B5 64.4(5) . . ? B3 C1 B5 117.0(6) . . ? B3 C2 C11 116.6(9) . . ? B3 C2 C1 65.3(7) . . ? C11 C2 C1 116.6(8) . . ? B3 C2 B11 118.2(9) . . ? C11 C2 B11 118.7(10) . . ? C1 C2 B11 109.5(6) . . ? B3 C2 B7 67.3(8) . . ? C11 C2 B7 123.0(7) . . ? C1 C2 B7 115.1(7) . . ? B11 C2 B7 60.9(6) . . ? B3 C2 B6 115.0(7) . . ? C11 C2 B6 115.1(8) . . ? C1 C2 B6 57.8(5) . . ? B11 C2 B6 61.3(5) . . ? B7 C2 B6 111.5(7) . . ? C17 C12 C13 116.2(5) . . ? C17 C12 B5 128.9(4) . . ? C13 C12 B5 114.5(4) . . ? C14 C13 C12 121.8(5) . . ? C15 C14 C13 121.3(5) . . ? C14 C15 C16 118.6(6) . . ? C15 C16 C17 122.0(5) . . ? C12 C17 C16 120.1(4) . . ? C12 C17 C18 123.7(4) . . ? C16 C17 C18 116.2(4) . . ? N2 C18 N1 126.7(5) . . ? N2 C18 C17 116.6(4) . . ? N1 C18 C17 116.6(5) . . ? N1 C19 C20 122.7(5) . . ? C21 C20 C19 116.8(6) . . ? N2 C21 C20 123.1(6) . . ? C2 B3 C1 58.4(6) . . ? C2 B3 B8 107.3(11) . . ? C1 B3 B8 104.7(7) . . ? C2 B3 B4 105.6(8) . . ? C1 B3 B4 57.0(5) . . ? B8 B3 B4 60.8(7) . . ? C2 B3 B7 60.6(8) . . ? C1 B3 B7 105.2(9) . . ? B8 B3 B7 59.1(8) . . ? B4 B3 B7 107.1(9) . . ? C1 B4 B9 106.4(8) . . ? C1 B4 B3 60.3(6) . . ? B9 B4 B3 108.8(9) . . ? C1 B4 B8 105.5(7) . . ? B9 B4 B8 61.3(7) . . ? B3 B4 B8 58.5(7) . . ? C1 B4 B5 60.2(4) . . ? B9 B4 B5 61.2(5) . . ? B3 B4 B5 111.4(8) . . ? B8 B4 B5 111.0(8) . . ? C12 B5 C1 125.0(5) . . ? C12 B5 B6 124.5(5) . . ? C1 B5 B6 54.6(5) . . ? C12 B5 B10 125.9(5) . . ? C1 B5 B10 100.5(5) . . ? B6 B5 B10 58.6(5) . . ? C12 B5 B9 125.6(5) . . ? C1 B5 B9 99.6(5) . . ? B6 B5 B9 105.6(6) . . ? B10 B5 B9 62.7(7) . . ? C12 B5 B4 122.9(5) . . ? C1 B5 B4 55.4(5) . . ? B6 B5 B4 101.0(5) . . ? B10 B5 B4 105.8(6) . . ? B9 B5 B4 57.1(7) . . ? C1 B6 C2 56.8(5) . . ? C1 B6 B11 105.6(7) . . ? C2 B6 B11 57.6(6) . . ? C1 B6 B10 107.2(6) . . ? C2 B6 B10 106.0(6) . . ? B11 B6 B10 63.1(6) . . ? C1 B6 B5 61.1(4) . . ? C2 B6 B5 106.9(6) . . ? B11 B6 B5 112.2(6) . . ? B10 B6 B5 60.8(5) . . ? B11 B7 C2 58.1(6) . . ? B11 B7 B12 62.2(8) . . ? C2 B7 B12 105.4(7) . . ? B11 B7 B8 111.5(7) . . ? C2 B7 B8 98.9(7) . . ? B12 B7 B8 66.2(9) . . ? B11 B7 B3 103.0(7) . . ? C2 B7 B3 52.1(6) . . ? B12 B7 B3 109.3(8) . . ? B8 B7 B3 57.1(8) . . ? B3 B8 B7 63.8(8) . . ? B3 B8 B4 60.7(8) . . ? B7 B8 B4 110.7(7) . . ? B3 B8 B9 108.3(7) . . ? B7 B8 B9 107.8(9) . . ? B4 B8 B9 58.6(6) . . ? B3 B8 B12 107.1(9) . . ? B7 B8 B12 56.6(7) . . ? B4 B8 B12 106.1(7) . . ? B9 B8 B12 60.4(8) . . ? B4 B9 B8 60.1(8) . . ? B4 B9 B5 61.7(5) . . ? B8 B9 B5 110.4(7) . . ? B4 B9 B12 109.4(7) . . ? B8 B9 B12 63.2(7) . . ? B5 B9 B12 106.7(8) . . ? B4 B9 B10 106.0(6) . . ? B8 B9 B10 107.0(7) . . ? B5 B9 B10 58.4(5) . . ? B12 B9 B10 56.7(7) . . ? B6 B10 B12 107.2(7) . . ? B6 B10 B5 60.7(4) . . ? B12 B10 B5 111.0(8) . . ? B6 B10 B11 58.2(6) . . ? B12 B10 B11 59.7(6) . . ? B5 B10 B11 108.2(6) . . ? B6 B10 B9 104.3(6) . . ? B12 B10 B9 61.2(8) . . ? B5 B10 B9 58.9(5) . . ? B11 B10 B9 105.3(6) . . ? C2 B11 B7 61.0(7) . . ? C2 B11 B6 61.1(6) . . ? B7 B11 B6 111.5(8) . . ? C2 B11 B12 105.2(9) . . ? B7 B11 B12 59.2(6) . . ? B6 B11 B12 106.6(7) . . ? C2 B11 B10 105.3(6) . . ? B7 B11 B10 107.2(8) . . ? B6 B11 B10 58.7(5) . . ? B12 B11 B10 58.4(6) . . ? B7 B12 B10 109.6(8) . . ? B7 B12 B11 58.6(7) . . ? B10 B12 B11 61.9(7) . . ? B7 B12 B9 104.8(10) . . ? B10 B12 B9 62.1(6) . . ? B11 B12 B9 107.6(6) . . ? B7 B12 B8 57.2(7) . . ? B10 B12 B8 105.9(8) . . ? B11 B12 B8 102.1(8) . . ? B9 B12 B8 56.3(8) . . ? 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 1.329(6) . ? N1 C19 1.344(7) . ? N2 C18 1.323(6) . ? N2 C21 1.338(7) . ? C1 C2 1.575(11) . ? C1 B6 1.592(13) . ? C1 B4 1.622(13) . ? C1 B3 1.680(12) . ? C1 B5 1.710(9) . ? C2 B3 1.539(17) . ? C2 C11 1.540(12) . ? C2 B11 1.648(15) . ? C2 B7 1.699(13) . ? C2 B6 1.711(12) . ? C12 C17 1.400(7) . ? C12 C13 1.427(7) . ? C12 B5 1.570(8) . ? C13 C14 1.370(8) . ? C14 C15 1.364(9) . ? C15 C16 1.373(8) . ? C16 C17 1.402(7) . ? C17 C18 1.495(7) . ? C19 C20 1.360(9) . ? C20 C21 1.353(9) . ? B3 B8 1.682(19) . ? B3 B4 1.720(16) . ? B3 B7 1.80(2) . ? B4 B9 1.695(19) . ? B4 B8 1.721(17) . ? B4 B5 1.778(10) . ? B5 B6 1.758(9) . ? B5 B10 1.760(10) . ? B5 B9 1.769(9) . ? B6 B11 1.713(11) . ? B6 B10 1.722(14) . ? B7 B11 1.696(15) . ? B7 B12 1.707(15) . ? B7 B8 1.719(16) . ? B8 B9 1.743(16) . ? B8 B12 1.87(2) . ? B9 B12 1.82(2) . ? B9 B10 1.837(18) . ? B10 B12 1.736(14) . ? B10 B11 1.797(16) . ? B11 B12 1.759(18) . ?