#------------------------------------------------------------------------------ #$Date: 2020-05-16 04:10:18 +0300 (Sat, 16 May 2020) $ #$Revision: 252064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126537.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_7126537 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 Mixed Directing-Group Strategy ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/D0CC02531C _journal_year 2020 _chemical_formula_sum 'C14 H21 B10 N' _chemical_formula_weight 311.42 _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 96.9162(15) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.8752(10) _cell_length_b 7.2500(4) _cell_length_c 13.1539(7) _cell_measurement_reflns_used 167 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 15 _cell_measurement_theta_min 15 _cell_volume 1786.95(17) _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 296(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _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 0.0510 _diffrn_reflns_av_unetI/netI 0.0292 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _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 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 28391 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.240 _diffrn_reflns_theta_min 3.013 _exptl_absorpt_coefficient_mu 0.058 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6634 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.158 _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 0.228 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 3235 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0826 _refine_ls_R_factor_gt 0.0577 _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^)+(0.0739P)^2^+0.8575P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1432 _refine_ls_wR_factor_ref 0.1597 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2386 _reflns_number_total 3235 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc02531c2.cif _cod_data_source_block 3aa _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7126537 _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 18.87520 7.25000 13.15390 90.0000 96.9162 90.0000 ZERR 4.00 0.00100 0.00040 0.00070 0.0000 0.0015 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H B N UNIT 56 84 40 4 REM C14 H21 B10 N REM D8VENTURE BLOCK COLOURLESS OMIT -3 50.5 SIZE 0.40 0.30 0.20 L.S. 4 ACTA FMAP 2 PLAN 20 TEMP 23 WGHT 0.073900 0.857500 FVAR 0.29833 N1 4 0.160938 0.408863 0.457508 11.00000 0.04614 0.05125 = 0.03856 -0.00285 0.00438 -0.00131 C1 1 0.302623 0.555529 0.554247 11.00000 0.03549 0.05165 = 0.04233 -0.00046 0.00339 -0.00594 AFIX 153 H1 2 0.267572 0.536876 0.481900 11.00000 -1.20000 AFIX 0 C2 1 0.373095 0.423596 0.580829 11.00000 0.03612 0.05067 = 0.04879 -0.00898 0.00899 -0.00263 C11 1 0.387340 0.276328 0.504524 11.00000 0.05546 0.08342 = 0.08446 -0.03795 0.02068 -0.00323 AFIX 33 H11A 2 0.429901 0.210047 0.529654 11.00000 -1.50000 H11B 2 0.347726 0.192470 0.495281 11.00000 -1.50000 H11C 2 0.393440 0.332933 0.440176 11.00000 -1.50000 AFIX 0 C12 1 0.179491 0.642092 0.660910 11.00000 0.03962 0.03157 = 0.03611 0.00493 0.00466 0.00505 C13 1 0.161099 0.784007 0.724770 11.00000 0.04469 0.03694 = 0.05324 -0.00464 0.00522 0.00365 AFIX 43 H13A 2 0.197364 0.857319 0.757441 11.00000 -1.20000 AFIX 0 C14 1 0.091851 0.820442 0.741614 11.00000 0.05221 0.04339 = 0.05879 -0.00531 0.01339 0.01120 AFIX 43 H14A 2 0.082244 0.916379 0.784846 11.00000 -1.20000 AFIX 0 C15 1 0.037168 0.715267 0.694642 11.00000 0.03854 0.05872 = 0.06044 0.00290 0.01285 0.01039 AFIX 43 H15A 2 -0.009770 0.738973 0.705430 11.00000 -1.20000 AFIX 0 C16 1 0.052835 0.573905 0.631206 11.00000 0.03727 0.05420 = 0.04783 0.00102 0.00406 -0.00057 AFIX 43 H16A 2 0.015768 0.502055 0.599458 11.00000 -1.20000 AFIX 0 C17 1 0.122542 0.535054 0.613053 11.00000 0.03727 0.03793 = 0.03510 0.00595 0.00367 0.00425 C18 1 0.131068 0.376920 0.543202 11.00000 0.03373 0.04110 = 0.03804 0.00073 -0.00244 0.00159 C19 1 0.106080 0.203560 0.565446 11.00000 0.06294 0.04692 = 0.05215 0.00138 0.01048 -0.00514 AFIX 43 H19A 2 0.084646 0.184858 0.624672 11.00000 -1.20000 AFIX 0 C20 1 0.113139 0.059336 0.499499 11.00000 0.07764 0.04087 = 0.07289 -0.00468 0.00210 -0.00681 AFIX 43 H20A 2 0.096944 -0.057944 0.513673 11.00000 -1.20000 AFIX 0 C21 1 0.144512 0.091759 0.412442 11.00000 0.06532 0.05605 = 0.05986 -0.02071 -0.00112 0.00623 AFIX 43 H21A 2 0.150173 -0.002861 0.366369 11.00000 -1.20000 AFIX 0 C22 1 0.167254 0.266733 0.395113 11.00000 0.05356 0.06470 = 0.04278 -0.01165 0.00630 0.00199 AFIX 43 H22A 2 0.188498 0.287850 0.335955 11.00000 -1.20000 AFIX 0 B3 3 0.384908 0.649485 0.546975 11.00000 0.04032 0.06243 = 0.05608 0.01798 0.00652 -0.00960 AFIX 153 H3 2 0.405321 0.693388 0.475923 11.00000 -1.20000 AFIX 0 B4 3 0.316413 0.772246 0.598816 11.00000 0.04176 0.03864 = 0.07347 0.01148 -0.00245 -0.00493 AFIX 153 H4 2 0.292411 0.897373 0.561991 11.00000 -1.20000 AFIX 0 B5 3 0.262573 0.612064 0.658903 11.00000 0.03920 0.03251 = 0.03755 0.00054 0.00167 0.00229 B6 3 0.300805 0.391074 0.646088 11.00000 0.03567 0.03502 = 0.06091 0.00143 0.01219 0.00049 AFIX 153 H6 2 0.267190 0.266703 0.639166 11.00000 -1.20000 AFIX 0 B7 3 0.440215 0.544419 0.647603 11.00000 0.03494 0.05259 = 0.05128 -0.00161 0.00162 -0.00176 AFIX 153 H7 2 0.497196 0.519722 0.642635 11.00000 -1.20000 AFIX 0 B8 3 0.404912 0.767761 0.662370 11.00000 0.04156 0.04526 = 0.08776 -0.00557 -0.00598 -0.00563 AFIX 153 H8 2 0.439023 0.891243 0.668081 11.00000 -1.20000 AFIX 0 B9 3 0.331011 0.745634 0.732580 11.00000 0.04438 0.05551 = 0.06081 -0.02106 -0.00549 0.00651 AFIX 153 H9 2 0.317204 0.855040 0.784694 11.00000 -1.20000 AFIX 0 B10 3 0.320473 0.510350 0.761183 11.00000 0.04513 0.06890 = 0.03972 0.01213 0.00755 0.01494 AFIX 153 H10 2 0.299593 0.465832 0.831781 11.00000 -1.20000 AFIX 0 B11 3 0.388550 0.386785 0.709385 11.00000 0.04149 0.05248 = 0.05741 0.01478 0.00931 0.01249 AFIX 153 H11 2 0.412102 0.260193 0.745066 11.00000 -1.20000 AFIX 0 B12 3 0.407387 0.605963 0.762683 11.00000 0.04318 0.07510 = 0.04791 -0.01161 -0.00738 0.01114 AFIX 153 H12 2 0.443316 0.623878 0.834284 11.00000 -1.20000 AFIX 0 HKLF 4 REM P in P2(1)/c REM R1 = 0.0577 for 2386 Fo > 4sig(Fo) and 0.0826 for all 3235 data REM 226 parameters refined using 0 restraints END WGHT 0.0731 0.8742 REM Highest difference peak 0.228, deepest hole -0.226, 1-sigma level 0.042 Q1 1 0.3973 0.6148 0.4586 11.00000 0.05 0.23 Q2 1 0.4394 0.2928 0.4837 11.00000 0.05 0.20 Q3 1 0.3497 0.2806 0.4368 11.00000 0.05 0.18 Q4 1 0.2959 0.8501 0.5273 11.00000 0.05 0.17 Q5 1 0.3889 0.7213 0.7265 11.00000 0.05 0.16 Q6 1 0.3017 0.7261 0.6637 11.00000 0.05 0.16 Q7 1 0.3615 0.3771 0.6435 11.00000 0.05 0.16 Q8 1 0.3772 0.4950 0.7552 11.00000 0.05 0.15 Q9 1 0.3833 0.1226 0.5398 11.00000 0.05 0.15 Q10 1 0.3080 0.6323 0.7353 11.00000 0.05 0.15 Q11 1 0.2962 0.4554 0.5940 11.00000 0.05 0.14 Q12 1 0.2763 0.2748 0.5976 11.00000 0.05 0.14 Q13 1 0.3489 0.7557 0.6633 11.00000 0.05 0.14 Q14 1 0.2917 0.4826 0.6950 11.00000 0.05 0.14 Q15 1 0.2208 0.6176 0.6577 11.00000 0.05 0.14 Q16 1 0.2105 0.8762 0.8040 11.00000 0.05 0.14 Q17 1 0.3977 0.2110 0.7051 11.00000 0.05 0.13 Q18 1 0.3731 0.7525 0.5883 11.00000 0.05 0.13 Q19 1 0.3542 0.5262 0.5464 11.00000 0.05 0.12 Q20 1 0.4220 0.5530 0.8694 11.00000 0.05 0.12 ; _shelx_res_checksum 13198 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 0.16094(9) 0.4089(3) 0.45751(13) 0.0454(5) Uani 1 1 d . . . . . C1 C 0.30262(10) 0.5555(3) 0.55425(16) 0.0433(5) Uani 1 1 d . . . . . H1 H 0.2676 0.5369 0.4819 0.052 Uiso 1 1 calc R U . . . C2 C 0.37310(11) 0.4236(3) 0.58083(16) 0.0449(5) Uani 1 1 d . . . . . C11 C 0.38734(14) 0.2763(4) 0.5045(2) 0.0735(8) Uani 1 1 d . . . . . H11A H 0.4299 0.2100 0.5297 0.110 Uiso 1 1 calc R U . . . H11B H 0.3477 0.1925 0.4953 0.110 Uiso 1 1 calc R U . . . H11C H 0.3934 0.3329 0.4402 0.110 Uiso 1 1 calc R U . . . C12 C 0.17949(10) 0.6421(3) 0.66091(14) 0.0358(5) Uani 1 1 d . . . . . C13 C 0.16110(11) 0.7840(3) 0.72477(16) 0.0450(5) Uani 1 1 d . . . . . H13A H 0.1974 0.8573 0.7574 0.054 Uiso 1 1 calc R U . . . C14 C 0.09185(12) 0.8204(3) 0.74161(18) 0.0509(6) Uani 1 1 d . . . . . H14A H 0.0822 0.9164 0.7848 0.061 Uiso 1 1 calc R U . . . C15 C 0.03717(12) 0.7153(3) 0.69464(18) 0.0520(6) Uani 1 1 d . . . . . H15A H -0.0098 0.7390 0.7054 0.062 Uiso 1 1 calc R U . . . C16 C 0.05284(11) 0.5739(3) 0.63121(16) 0.0465(5) Uani 1 1 d . . . . . H16A H 0.0158 0.5021 0.5995 0.056 Uiso 1 1 calc R U . . . C17 C 0.12254(10) 0.5351(3) 0.61305(14) 0.0368(5) Uani 1 1 d . . . . . C18 C 0.13107(10) 0.3769(3) 0.54320(15) 0.0382(5) Uani 1 1 d . . . . . C19 C 0.10608(13) 0.2036(3) 0.56545(18) 0.0537(6) Uani 1 1 d . . . . . H19A H 0.0846 0.1849 0.6247 0.064 Uiso 1 1 calc R U . . . C20 C 0.11314(14) 0.0593(3) 0.4995(2) 0.0644(7) Uani 1 1 d . . . . . H20A H 0.0969 -0.0579 0.5137 0.077 Uiso 1 1 calc R U . . . C21 C 0.14451(13) 0.0918(4) 0.4124(2) 0.0611(7) Uani 1 1 d . . . . . H21A H 0.1502 -0.0029 0.3664 0.073 Uiso 1 1 calc R U . . . C22 C 0.16725(12) 0.2667(4) 0.39511(17) 0.0536(6) Uani 1 1 d . . . . . H22A H 0.1885 0.2879 0.3360 0.064 Uiso 1 1 calc R U . . . B3 B 0.38491(14) 0.6495(4) 0.5470(2) 0.0529(7) Uani 1 1 d . . . . . H3 H 0.4053 0.6934 0.4759 0.063 Uiso 1 1 calc R U . . . B4 B 0.31641(13) 0.7722(4) 0.5988(2) 0.0521(7) Uani 1 1 d . . . . . H4 H 0.2924 0.8974 0.5620 0.062 Uiso 1 1 calc R U . . . B5 B 0.26257(12) 0.6121(3) 0.65890(17) 0.0367(5) Uani 1 1 d . . . . . B6 B 0.30080(12) 0.3911(3) 0.6461(2) 0.0433(6) Uani 1 1 d . . . . . H6 H 0.2672 0.2667 0.6392 0.052 Uiso 1 1 calc R U . . . B7 B 0.44022(13) 0.5444(4) 0.64760(19) 0.0466(6) Uani 1 1 d . . . . . H7 H 0.4972 0.5197 0.6426 0.056 Uiso 1 1 calc R U . . . B8 B 0.40491(14) 0.7678(4) 0.6624(2) 0.0593(8) Uani 1 1 d . . . . . H8 H 0.4390 0.8912 0.6681 0.071 Uiso 1 1 calc R U . . . B9 B 0.33101(14) 0.7456(4) 0.7326(2) 0.0545(7) Uani 1 1 d . . . . . H9 H 0.3172 0.8550 0.7847 0.065 Uiso 1 1 calc R U . . . B10 B 0.32047(14) 0.5103(4) 0.76118(19) 0.0511(7) Uani 1 1 d . . . . . H10 H 0.2996 0.4658 0.8318 0.061 Uiso 1 1 calc R U . . . B11 B 0.38855(13) 0.3868(4) 0.7094(2) 0.0502(7) Uani 1 1 d . . . . . H11 H 0.4121 0.2602 0.7451 0.060 Uiso 1 1 calc R U . . . B12 B 0.40739(14) 0.6060(4) 0.7627(2) 0.0564(7) Uani 1 1 d . . . . . H12 H 0.4433 0.6239 0.8343 0.068 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 0.0461(10) 0.0512(11) 0.0386(10) -0.0028(8) 0.0044(8) -0.0013(8) C1 0.0355(11) 0.0516(13) 0.0423(11) -0.0005(10) 0.0034(9) -0.0059(9) C2 0.0361(11) 0.0507(13) 0.0488(12) -0.0090(10) 0.0090(9) -0.0026(9) C11 0.0555(15) 0.083(2) 0.0845(19) -0.0379(16) 0.0207(13) -0.0032(14) C12 0.0396(11) 0.0316(10) 0.0361(10) 0.0049(8) 0.0047(8) 0.0051(8) C13 0.0447(12) 0.0369(11) 0.0532(13) -0.0046(10) 0.0052(10) 0.0037(9) C14 0.0522(14) 0.0434(13) 0.0588(14) -0.0053(11) 0.0134(11) 0.0112(10) C15 0.0385(12) 0.0587(15) 0.0604(14) 0.0029(12) 0.0128(10) 0.0104(10) C16 0.0373(11) 0.0542(14) 0.0478(12) 0.0010(11) 0.0041(9) -0.0006(10) C17 0.0373(11) 0.0379(11) 0.0351(10) 0.0059(9) 0.0037(8) 0.0042(9) C18 0.0337(10) 0.0411(12) 0.0380(11) 0.0007(9) -0.0024(8) 0.0016(9) C19 0.0629(15) 0.0469(14) 0.0521(13) 0.0014(11) 0.0105(11) -0.0051(11) C20 0.0776(18) 0.0409(14) 0.0729(17) -0.0047(13) 0.0021(14) -0.0068(12) C21 0.0653(16) 0.0561(16) 0.0599(15) -0.0207(13) -0.0011(12) 0.0062(13) C22 0.0536(14) 0.0647(16) 0.0428(12) -0.0116(12) 0.0063(10) 0.0020(12) B3 0.0403(14) 0.0624(17) 0.0561(15) 0.0180(14) 0.0065(11) -0.0096(12) B4 0.0418(14) 0.0386(14) 0.0735(18) 0.0115(13) -0.0025(12) -0.0049(11) B5 0.0392(12) 0.0325(12) 0.0376(12) 0.0005(10) 0.0017(9) 0.0023(10) B6 0.0357(12) 0.0350(13) 0.0609(15) 0.0014(11) 0.0122(11) 0.0005(10) B7 0.0349(12) 0.0526(15) 0.0513(14) -0.0016(12) 0.0016(10) -0.0018(11) B8 0.0416(15) 0.0453(15) 0.088(2) -0.0056(15) -0.0060(14) -0.0056(12) B9 0.0444(14) 0.0555(16) 0.0608(17) -0.0211(14) -0.0055(12) 0.0065(12) B10 0.0451(14) 0.0689(18) 0.0397(13) 0.0121(13) 0.0075(11) 0.0149(13) B11 0.0415(14) 0.0525(15) 0.0574(15) 0.0148(13) 0.0093(11) 0.0125(12) B12 0.0432(14) 0.075(2) 0.0479(15) -0.0116(14) -0.0074(11) 0.0111(13) 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 C22 N1 C18 117.56(19) . . ? C2 C1 B4 112.44(16) . . ? C2 C1 B5 113.35(16) . . ? B4 C1 B5 63.80(14) . . ? C2 C1 B6 61.66(13) . . ? B4 C1 B6 114.95(17) . . ? B5 C1 B6 62.90(13) . . ? C2 C1 B3 61.68(14) . . ? B4 C1 B3 62.92(16) . . ? B5 C1 B3 116.44(17) . . ? B6 C1 B3 114.54(17) . . ? C11 C2 C1 118.33(19) . . ? C11 C2 B7 121.82(18) . . ? C1 C2 B7 110.18(17) . . ? C11 C2 B11 121.7(2) . . ? C1 C2 B11 109.91(16) . . ? B7 C2 B11 62.51(15) . . ? C11 C2 B6 116.84(19) . . ? C1 C2 B6 60.87(13) . . ? B7 C2 B6 113.70(17) . . ? B11 C2 B6 62.11(14) . . ? C11 C2 B3 117.5(2) . . ? C1 C2 B3 61.10(14) . . ? B7 C2 B3 61.96(15) . . ? B11 C2 B3 113.25(18) . . ? B6 C2 B3 113.38(17) . . ? C13 C12 C17 116.22(18) . . ? C13 C12 B5 115.37(18) . . ? C17 C12 B5 128.21(17) . . ? C14 C13 C12 123.2(2) . . ? C15 C14 C13 119.9(2) . . ? C14 C15 C16 118.9(2) . . ? C15 C16 C17 122.0(2) . . ? C16 C17 C12 119.77(19) . . ? C16 C17 C18 115.81(18) . . ? C12 C17 C18 124.42(17) . . ? N1 C18 C19 121.51(19) . . ? N1 C18 C17 118.26(18) . . ? C19 C18 C17 120.19(18) . . ? C20 C19 C18 119.7(2) . . ? C21 C20 C19 118.7(2) . . ? C22 C21 C20 118.3(2) . . ? N1 C22 C21 124.2(2) . . ? C1 B3 C2 57.22(13) . . ? C1 B3 B8 104.48(19) . . ? C2 B3 B8 105.32(19) . . ? C1 B3 B7 104.27(18) . . ? C2 B3 B7 58.38(14) . . ? B8 B3 B7 60.73(16) . . ? C1 B3 B4 57.91(14) . . ? C2 B3 B4 104.80(17) . . ? B8 B3 B4 60.65(16) . . ? B7 B3 B4 108.8(2) . . ? C1 B4 B9 104.16(18) . . ? C1 B4 B3 59.17(14) . . ? B9 B4 B3 107.23(19) . . ? C1 B4 B8 104.10(18) . . ? B9 B4 B8 60.12(16) . . ? B3 B4 B8 58.90(16) . . ? C1 B4 B5 58.44(13) . . ? B9 B4 B5 61.02(15) . . ? B3 B4 B5 108.88(18) . . ? B8 B4 B5 109.41(19) . . ? C12 B5 C1 125.72(17) . . ? C12 B5 B6 122.67(17) . . ? C1 B5 B6 58.61(13) . . ? C12 B5 B10 124.06(17) . . ? C1 B5 B10 102.65(16) . . ? B6 B5 B10 58.66(14) . . ? C12 B5 B4 122.24(17) . . ? C1 B5 B4 57.76(14) . . ? B6 B5 B4 106.57(16) . . ? B10 B5 B4 105.79(17) . . ? C12 B5 B9 124.30(18) . . ? C1 B5 B9 101.86(16) . . ? B6 B5 B9 105.26(17) . . ? B10 B5 B9 58.86(15) . . ? B4 B5 B9 58.66(15) . . ? C1 B6 C2 57.47(13) . . ? C1 B6 B10 104.39(17) . . ? C2 B6 B10 105.52(17) . . ? C1 B6 B11 104.47(16) . . ? C2 B6 B11 58.62(13) . . ? B10 B6 B11 60.59(15) . . ? C1 B6 B5 58.49(13) . . ? C2 B6 B5 106.32(16) . . ? B10 B6 B5 61.06(14) . . ? B11 B6 B5 109.94(18) . . ? C2 B7 B3 59.66(14) . . ? C2 B7 B12 104.94(17) . . ? B3 B7 B12 107.40(19) . . ? C2 B7 B11 58.92(14) . . ? B3 B7 B11 108.47(17) . . ? B12 B7 B11 59.77(16) . . ? C2 B7 B8 105.17(17) . . ? B3 B7 B8 59.27(16) . . ? B12 B7 B8 59.86(17) . . ? B11 B7 B8 107.81(18) . . ? B3 B8 B12 107.92(19) . . ? B3 B8 B9 107.92(18) . . ? B12 B8 B9 60.04(16) . . ? B3 B8 B7 60.00(15) . . ? B12 B8 B7 59.80(15) . . ? B9 B8 B7 107.8(2) . . ? B3 B8 B4 60.44(16) . . ? B12 B8 B4 107.66(19) . . ? B9 B8 B4 59.45(15) . . ? B7 B8 B4 108.07(19) . . ? B4 B9 B10 108.15(19) . . ? B4 B9 B12 108.20(19) . . ? B10 B9 B12 60.51(16) . . ? B4 B9 B8 60.43(16) . . ? B10 B9 B8 108.37(19) . . ? B12 B9 B8 59.74(16) . . ? B4 B9 B5 60.32(14) . . ? B10 B9 B5 60.18(14) . . ? B12 B9 B5 108.99(19) . . ? B8 B9 B5 109.09(19) . . ? B6 B10 B9 108.19(18) . . ? B6 B10 B11 60.21(15) . . ? B9 B10 B11 107.57(19) . . ? B6 B10 B12 107.60(17) . . ? B9 B10 B12 59.85(16) . . ? B11 B10 B12 59.33(15) . . ? B6 B10 B5 60.28(13) . . ? B9 B10 B5 60.96(14) . . ? B11 B10 B5 109.01(17) . . ? B12 B10 B5 109.09(19) . . ? C2 B11 B12 104.89(18) . . ? C2 B11 B6 59.26(14) . . ? B12 B11 B6 107.84(18) . . ? C2 B11 B7 58.57(13) . . ? B12 B11 B7 60.05(16) . . ? B6 B11 B7 108.14(17) . . ? C2 B11 B10 104.94(17) . . ? B12 B11 B10 60.62(16) . . ? B6 B11 B10 59.20(14) . . ? B7 B11 B10 108.48(19) . . ? B11 B12 B7 60.18(15) . . ? B11 B12 B8 108.52(19) . . ? B7 B12 B8 60.35(16) . . ? B11 B12 B9 107.98(18) . . ? B7 B12 B9 108.34(19) . . ? B8 B12 B9 60.22(16) . . ? B11 B12 B10 60.05(16) . . ? B7 B12 B10 108.13(18) . . ? B8 B12 B10 108.05(18) . . ? B9 B12 B10 59.63(15) . . ? 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 C22 1.332(3) . ? N1 C18 1.340(3) . ? C1 C2 1.642(3) . ? C1 B4 1.686(3) . ? C1 B5 1.699(3) . ? C1 B6 1.701(3) . ? C1 B3 1.709(3) . ? C2 C11 1.512(3) . ? C2 B7 1.696(3) . ? C2 B11 1.702(3) . ? C2 B6 1.714(3) . ? C2 B3 1.719(4) . ? C12 C13 1.398(3) . ? C12 C17 1.411(3) . ? C12 B5 1.587(3) . ? C13 C14 1.377(3) . ? C14 C15 1.369(3) . ? C15 C16 1.376(3) . ? C16 C17 1.394(3) . ? C17 C18 1.490(3) . ? C18 C19 1.386(3) . ? C19 C20 1.375(3) . ? C20 C21 1.371(4) . ? C21 C22 1.367(3) . ? B3 B8 1.745(4) . ? B3 B7 1.758(4) . ? B3 B4 1.772(4) . ? B4 B9 1.758(4) . ? B4 B8 1.776(4) . ? B4 B5 1.789(3) . ? B5 B6 1.774(3) . ? B5 B10 1.787(3) . ? B5 B9 1.801(3) . ? B6 B10 1.744(4) . ? B6 B11 1.762(3) . ? B7 B12 1.761(4) . ? B7 B11 1.763(4) . ? B7 B8 1.771(4) . ? B8 B12 1.762(4) . ? B8 B9 1.771(4) . ? B9 B10 1.763(4) . ? B9 B12 1.767(4) . ? B10 B11 1.769(4) . ? B10 B12 1.779(4) . ? B11 B12 1.756(4) . ?