#------------------------------------------------------------------------------ #$Date: 2020-07-06 04:44:48 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253776 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126540.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_7126540 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 H29 B20 N' _chemical_formula_weight 415.57 _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 92.9866(17) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.1083(4) _cell_length_b 15.2069(5) _cell_length_c 13.3711(5) _cell_measurement_reflns_used 1107 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 15 _cell_measurement_theta_min 15 _cell_volume 2458.67(15) _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 0.0442 _diffrn_reflns_av_unetI/netI 0.0233 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 29884 _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 1.684 _exptl_absorpt_coefficient_mu 0.052 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6997 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.123 _exptl_crystal_description block _exptl_crystal_F_000 856 _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.271 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 307 _refine_ls_number_reflns 4446 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0602 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1152P)^2^+0.8062P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1767 _refine_ls_wR_factor_ref 0.1884 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3689 _reflns_number_total 4446 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc02531c2.cif _cod_data_source_block 3ax _cod_depositor_comments 'Adding full bibliography for 7126537--7126543.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7126540 _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 0.980 _shelx_estimated_absorpt_t_max 0.990 _shelxl_version_number 2014/6 _shelx_res_file ; TITL P in P2(1)/c CELL 0.71073 12.10830 15.20690 13.37110 90.0000 92.9866 90.0000 ZERR 4.00 0.00040 0.00050 0.00050 0.0000 0.0017 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H B N UNIT 52 116 80 4 OMIT -3 50.5 REM C13 H29 B20 N REM APEXII BLOCK COLOURLESS L.S. 4 ACTA FMAP 2 PLAN 20 SIZE 0.40 0.30 0.20 TEMP 23.000 WGHT 0.115200 0.806200 FVAR 0.16074 N1 4 0.872963 0.099628 0.504378 11.00000 0.09195 0.05153 = 0.08806 -0.02234 0.05386 -0.02485 C1 1 0.819303 -0.105468 0.557985 11.00000 0.05387 0.03343 = 0.06588 -0.00030 0.01180 0.00214 AFIX 153 H1 2 0.888537 -0.058608 0.564004 11.00000 -1.20000 AFIX 0 C2 1 0.798680 -0.169741 0.458536 11.00000 0.05539 0.03310 = 0.04750 -0.00013 0.00726 0.00473 C11 1 0.876797 -0.158791 0.374022 11.00000 0.07780 0.05624 = 0.06712 -0.00200 0.02810 0.00678 AFIX 33 H11A 2 0.856626 -0.199295 0.321108 11.00000 -1.50000 H11B 2 0.871874 -0.099719 0.348862 11.00000 -1.50000 H11C 2 0.951223 -0.170445 0.398723 11.00000 -1.50000 AFIX 0 C12 1 0.669202 0.017496 0.653378 11.00000 0.03791 0.03376 = 0.03973 0.00048 0.00287 -0.00222 C13 1 0.587968 0.019975 0.723415 11.00000 0.05068 0.03849 = 0.05829 0.00167 0.01769 -0.00813 AFIX 43 H13A 2 0.554003 -0.032164 0.741251 11.00000 -1.20000 AFIX 0 C14 1 0.556567 0.097624 0.766998 11.00000 0.04950 0.04839 = 0.06148 -0.00271 0.02451 -0.00297 AFIX 43 H14A 2 0.502814 0.097122 0.814204 11.00000 -1.20000 AFIX 0 C15 1 0.604450 0.175872 0.740922 11.00000 0.04379 0.03833 = 0.05589 -0.00582 0.01245 0.00272 AFIX 43 H15A 2 0.581540 0.227698 0.770408 11.00000 -1.20000 AFIX 0 C16 1 0.686436 0.179565 0.671450 11.00000 0.03657 0.03291 = 0.04152 -0.00286 0.00366 -0.00077 C17 1 0.717443 0.098464 0.629306 11.00000 0.03689 0.03249 = 0.03618 -0.00254 0.00379 -0.00242 C18 1 0.803665 0.099212 0.558956 11.00000 0.05672 0.02964 = 0.05416 -0.00873 0.01724 -0.01072 C19 1 0.851966 0.404607 0.408521 11.00000 0.07699 0.07090 = 0.06100 0.00832 0.01497 -0.02161 AFIX 33 H19A 2 0.836645 0.463331 0.385388 11.00000 -1.50000 H19B 2 0.929659 0.392907 0.405766 11.00000 -1.50000 H19C 2 0.811083 0.363451 0.366629 11.00000 -1.50000 AFIX 0 C21 1 0.837193 0.299164 0.570299 11.00000 0.04272 0.03037 = 0.05637 -0.00274 0.00652 -0.00256 AFIX 153 H21 2 0.874332 0.244568 0.529809 11.00000 -1.20000 AFIX 0 C22 1 0.818033 0.395338 0.515549 11.00000 0.04730 0.03702 = 0.05466 0.00212 0.00551 -0.00450 B3 3 0.710255 -0.086637 0.477097 11.00000 0.06021 0.02826 = 0.04286 0.00104 0.00999 0.00251 AFIX 153 H3 2 0.705117 -0.027909 0.429051 11.00000 -1.20000 AFIX 0 B4 3 0.694091 -0.075145 0.604863 11.00000 0.04112 0.03011 = 0.04087 0.00173 0.00395 -0.00380 B5 3 0.780006 -0.158390 0.662392 11.00000 0.07394 0.03816 = 0.04253 0.00334 -0.00739 0.00629 AFIX 153 H5 2 0.819284 -0.148330 0.737562 11.00000 -1.20000 AFIX 0 B6 3 0.847812 -0.215822 0.568132 11.00000 0.05898 0.03679 = 0.05845 -0.00054 -0.01141 0.01096 AFIX 153 H6 2 0.931602 -0.242855 0.581085 11.00000 -1.20000 AFIX 0 B7 3 0.661650 -0.187469 0.431784 11.00000 0.05699 0.05489 = 0.05696 -0.01506 -0.01567 0.00931 AFIX 153 H7 2 0.624042 -0.196169 0.355758 11.00000 -1.20000 AFIX 0 B8 3 0.593222 -0.130649 0.525444 11.00000 0.04008 0.05690 = 0.07307 -0.01826 -0.00490 0.00001 AFIX 153 H8 2 0.509976 -0.103025 0.510863 11.00000 -1.20000 AFIX 0 B9 3 0.637203 -0.177377 0.642794 11.00000 0.07512 0.03763 = 0.06706 -0.00336 0.02727 -0.01610 AFIX 153 H9 2 0.582372 -0.180528 0.705754 11.00000 -1.20000 AFIX 0 B10 3 0.731656 -0.262873 0.619856 11.00000 0.10900 0.02887 = 0.05915 0.00678 0.01476 -0.00279 AFIX 153 H10 2 0.738635 -0.321690 0.667655 11.00000 -1.20000 AFIX 0 B11 3 0.746840 -0.268904 0.489426 11.00000 0.06567 0.02987 = 0.05927 -0.00463 0.00224 -0.00223 AFIX 153 H11 2 0.764483 -0.330889 0.450968 11.00000 -1.20000 AFIX 0 B12 3 0.616415 -0.245716 0.536037 11.00000 0.06253 0.04886 = 0.09722 -0.02335 0.01889 -0.02290 AFIX 153 H12 2 0.547913 -0.293210 0.529248 11.00000 -1.20000 AFIX 0 B23 3 0.705541 0.329358 0.534692 11.00000 0.04269 0.04133 = 0.04751 0.00181 0.00353 -0.00377 AFIX 153 H23 2 0.654909 0.297822 0.474122 11.00000 -1.20000 AFIX 0 B24 3 0.734986 0.274273 0.649925 11.00000 0.03896 0.03159 = 0.04334 -0.00492 0.00359 -0.00171 B25 3 0.869134 0.309714 0.694693 11.00000 0.04492 0.03913 = 0.05609 0.00071 -0.00424 -0.00383 AFIX 153 H25 2 0.924081 0.265269 0.739045 11.00000 -1.20000 AFIX 0 B26 3 0.922019 0.384234 0.607298 11.00000 0.04000 0.03815 = 0.06767 -0.00192 0.00178 -0.00583 AFIX 153 H26 2 1.010759 0.388094 0.593919 11.00000 -1.20000 AFIX 0 B27 3 0.701330 0.443861 0.555543 11.00000 0.04803 0.03981 = 0.07158 0.00828 0.00389 0.00493 AFIX 153 H27 2 0.647284 0.487451 0.509159 11.00000 -1.20000 AFIX 0 B28 3 0.648382 0.369520 0.643261 11.00000 0.04285 0.03541 = 0.06014 -0.00287 0.00914 0.00364 AFIX 153 H28 2 0.559291 0.365072 0.654905 11.00000 -1.20000 AFIX 0 B29 3 0.749920 0.357543 0.743384 11.00000 0.05813 0.03996 = 0.04813 -0.01098 0.00539 -0.00483 AFIX 153 H29 2 0.726758 0.345275 0.820613 11.00000 -1.20000 AFIX 0 B30 3 0.865995 0.424679 0.717288 11.00000 0.06155 0.04139 = 0.06198 -0.01263 -0.00057 -0.01162 AFIX 153 H30 2 0.918217 0.455742 0.777107 11.00000 -1.20000 AFIX 0 B31 3 0.835108 0.477511 0.601225 11.00000 0.05633 0.02944 = 0.07549 -0.00375 0.00732 -0.00493 AFIX 153 H31 2 0.867594 0.543147 0.584521 11.00000 -1.20000 AFIX 0 B32 3 0.728993 0.461465 0.685286 11.00000 0.06432 0.03173 = 0.07437 -0.01162 0.01547 0.00067 AFIX 153 H32 2 0.692109 0.516827 0.724667 11.00000 -1.20000 AFIX 0 HKLF 4 REM P in P2(1)/c REM R1 = 0.0602 for 3689 Fo > 4sig(Fo) and 0.0701 for all 4446 data REM 307 parameters refined using 0 restraints END WGHT 0.1143 0.8149 REM Highest difference peak 0.271, deepest hole -0.226, 1-sigma level 0.042 Q1 1 0.7204 -0.0668 0.4670 11.00000 0.05 0.27 Q2 1 0.9331 -0.1127 0.3946 11.00000 0.05 0.26 Q3 1 0.6621 -0.0980 0.5034 11.00000 0.05 0.23 Q4 1 0.6823 -0.0275 0.6268 11.00000 0.05 0.23 Q5 1 0.7175 -0.0808 0.5195 11.00000 0.05 0.23 Q6 1 0.6885 -0.0883 0.5163 11.00000 0.05 0.22 Q7 1 0.7193 0.2243 0.6611 11.00000 0.05 0.22 Q8 1 0.7808 -0.2201 0.6192 11.00000 0.05 0.22 Q9 1 0.6791 0.3788 0.5763 11.00000 0.05 0.21 Q10 1 0.9133 -0.2195 0.3571 11.00000 0.05 0.21 Q11 1 0.6548 -0.2329 0.6048 11.00000 0.05 0.20 Q12 1 0.9996 0.3740 0.5589 11.00000 0.05 0.20 Q13 1 0.8841 0.4321 0.6508 11.00000 0.05 0.20 Q14 1 0.7171 0.1366 0.6570 11.00000 0.05 0.20 Q15 1 0.9087 0.4548 0.4031 11.00000 0.05 0.20 Q16 1 0.7043 -0.1552 0.6578 11.00000 0.05 0.20 Q17 1 0.6977 0.2892 0.4678 11.00000 0.05 0.20 Q18 1 0.6090 -0.1954 0.4950 11.00000 0.05 0.19 Q19 1 0.7537 0.4634 0.6199 11.00000 0.05 0.18 Q20 1 0.8805 0.3378 0.3807 11.00000 0.05 0.18 ; _shelx_res_checksum 94850 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 0.87296(19) 0.09963(12) 0.50438(17) 0.0755(7) Uani 1 1 d . . . . . C1 C 0.81930(18) -0.10547(12) 0.55798(16) 0.0508(5) Uani 1 1 d . . . . . H1 H 0.8885 -0.0586 0.5640 0.061 Uiso 1 1 calc R U . . . C2 C 0.79868(16) -0.16974(12) 0.45854(14) 0.0452(5) Uani 1 1 d . . . . . C11 C 0.8768(2) -0.15879(16) 0.37402(18) 0.0662(6) Uani 1 1 d . . . . . H11A H 0.8566 -0.1993 0.3211 0.099 Uiso 1 1 calc R U . . . H11B H 0.8719 -0.0997 0.3489 0.099 Uiso 1 1 calc R U . . . H11C H 0.9512 -0.1704 0.3987 0.099 Uiso 1 1 calc R U . . . C12 C 0.66920(14) 0.01750(11) 0.65338(13) 0.0371(4) Uani 1 1 d . . . . . C13 C 0.58797(16) 0.01998(13) 0.72341(15) 0.0486(5) Uani 1 1 d . . . . . H13A H 0.5540 -0.0322 0.7413 0.058 Uiso 1 1 calc R U . . . C14 C 0.55657(17) 0.09762(13) 0.76700(16) 0.0524(5) Uani 1 1 d . . . . . H14A H 0.5028 0.0971 0.8142 0.063 Uiso 1 1 calc R U . . . C15 C 0.60445(15) 0.17587(12) 0.74092(15) 0.0457(5) Uani 1 1 d . . . . . H15A H 0.5815 0.2277 0.7704 0.055 Uiso 1 1 calc R U . . . C16 C 0.68644(14) 0.17957(11) 0.67145(13) 0.0369(4) Uani 1 1 d . . . . . C17 C 0.71744(14) 0.09846(11) 0.62931(12) 0.0351(4) Uani 1 1 d . . . . . C18 C 0.80367(17) 0.09921(11) 0.55896(15) 0.0463(5) Uani 1 1 d . . . . . C19 C 0.8520(2) 0.40461(17) 0.40852(18) 0.0692(7) Uani 1 1 d . . . . . H19A H 0.8366 0.4633 0.3854 0.104 Uiso 1 1 calc R U . . . H19B H 0.9297 0.3929 0.4058 0.104 Uiso 1 1 calc R U . . . H19C H 0.8111 0.3635 0.3666 0.104 Uiso 1 1 calc R U . . . C21 C 0.83719(15) 0.29916(11) 0.57030(15) 0.0430(4) Uani 1 1 d . . . . . H21 H 0.8743 0.2446 0.5298 0.052 Uiso 1 1 calc R U . . . C22 C 0.81803(16) 0.39534(12) 0.51555(15) 0.0462(5) Uani 1 1 d . . . . . B3 B 0.71026(19) -0.08664(13) 0.47710(16) 0.0435(5) Uani 1 1 d . . . . . H3 H 0.7051 -0.0279 0.4291 0.052 Uiso 1 1 calc R U . . . B4 B 0.69409(16) -0.07514(13) 0.60486(15) 0.0373(4) Uani 1 1 d . . . . . B5 B 0.7800(2) -0.15839(15) 0.66239(17) 0.0519(6) Uani 1 1 d . . . . . H5 H 0.8193 -0.1483 0.7376 0.062 Uiso 1 1 calc R U . . . B6 B 0.8478(2) -0.21582(15) 0.56813(18) 0.0519(6) Uani 1 1 d . . . . . H6 H 0.9316 -0.2429 0.5811 0.062 Uiso 1 1 calc R U . . . B7 B 0.6617(2) -0.18747(17) 0.43178(19) 0.0569(6) Uani 1 1 d . . . . . H7 H 0.6240 -0.1962 0.3558 0.068 Uiso 1 1 calc R U . . . B8 B 0.59322(19) -0.13065(17) 0.5254(2) 0.0570(6) Uani 1 1 d . . . . . H8 H 0.5100 -0.1030 0.5109 0.068 Uiso 1 1 calc R U . . . B9 B 0.6372(2) -0.17738(15) 0.6428(2) 0.0591(7) Uani 1 1 d . . . . . H9 H 0.5824 -0.1805 0.7058 0.071 Uiso 1 1 calc R U . . . B10 B 0.7317(3) -0.26287(15) 0.6199(2) 0.0653(7) Uani 1 1 d . . . . . H10 H 0.7386 -0.3217 0.6677 0.078 Uiso 1 1 calc R U . . . B11 B 0.7468(2) -0.26890(14) 0.48943(18) 0.0516(6) Uani 1 1 d . . . . . H11 H 0.7645 -0.3309 0.4510 0.062 Uiso 1 1 calc R U . . . B12 B 0.6164(2) -0.24572(18) 0.5360(2) 0.0690(8) Uani 1 1 d . . . . . H12 H 0.5479 -0.2932 0.5292 0.083 Uiso 1 1 calc R U . . . B23 B 0.70554(18) 0.32936(14) 0.53469(16) 0.0438(5) Uani 1 1 d . . . . . H23 H 0.6549 0.2978 0.4741 0.053 Uiso 1 1 calc R U . . . B24 B 0.73499(16) 0.27427(13) 0.64993(15) 0.0379(4) Uani 1 1 d . . . . . B25 B 0.86913(18) 0.30971(14) 0.69469(17) 0.0469(5) Uani 1 1 d . . . . . H25 H 0.9241 0.2653 0.7390 0.056 Uiso 1 1 calc R U . . . B26 B 0.92202(18) 0.38423(14) 0.60730(19) 0.0486(5) Uani 1 1 d . . . . . H26 H 1.0108 0.3881 0.5939 0.058 Uiso 1 1 calc R U . . . B27 B 0.70133(19) 0.44386(15) 0.5555(2) 0.0531(6) Uani 1 1 d . . . . . H27 H 0.6473 0.4875 0.5092 0.064 Uiso 1 1 calc R U . . . B28 B 0.64838(18) 0.36952(14) 0.64326(18) 0.0459(5) Uani 1 1 d . . . . . H28 H 0.5593 0.3651 0.6549 0.055 Uiso 1 1 calc R U . . . B29 B 0.7499(2) 0.35754(15) 0.74338(17) 0.0486(5) Uani 1 1 d . . . . . H29 H 0.7268 0.3453 0.8206 0.058 Uiso 1 1 calc R U . . . B30 B 0.8660(2) 0.42468(16) 0.71729(19) 0.0551(6) Uani 1 1 d . . . . . H30 H 0.9182 0.4557 0.7771 0.066 Uiso 1 1 calc R U . . . B31 B 0.8351(2) 0.47751(15) 0.6012(2) 0.0536(6) Uani 1 1 d . . . . . H31 H 0.8676 0.5431 0.5845 0.064 Uiso 1 1 calc R U . . . B32 B 0.7290(2) 0.46147(15) 0.6853(2) 0.0564(6) Uani 1 1 d . . . . . H32 H 0.6921 0.5168 0.7247 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 0.0920(15) 0.0515(11) 0.0881(14) -0.0223(10) 0.0539(13) -0.0248(10) C1 0.0539(11) 0.0334(10) 0.0659(13) -0.0003(9) 0.0118(9) 0.0021(8) C2 0.0554(11) 0.0331(9) 0.0475(10) -0.0001(8) 0.0073(8) 0.0047(8) C11 0.0778(16) 0.0562(13) 0.0671(14) -0.0020(11) 0.0281(12) 0.0068(12) C12 0.0379(9) 0.0338(9) 0.0397(9) 0.0005(7) 0.0029(7) -0.0022(7) C13 0.0507(11) 0.0385(10) 0.0583(11) 0.0017(8) 0.0177(9) -0.0081(8) C14 0.0495(11) 0.0484(11) 0.0615(12) -0.0027(9) 0.0245(9) -0.0030(9) C15 0.0438(10) 0.0383(10) 0.0559(11) -0.0058(8) 0.0125(8) 0.0027(8) C16 0.0366(9) 0.0329(9) 0.0415(9) -0.0029(7) 0.0037(7) -0.0008(7) C17 0.0369(9) 0.0325(9) 0.0362(9) -0.0025(6) 0.0038(7) -0.0024(7) C18 0.0567(12) 0.0296(9) 0.0542(11) -0.0087(8) 0.0172(9) -0.0107(8) C19 0.0770(16) 0.0709(16) 0.0610(14) 0.0083(11) 0.0150(12) -0.0216(12) C21 0.0427(10) 0.0304(9) 0.0564(11) -0.0027(8) 0.0065(8) -0.0026(7) C22 0.0473(11) 0.0370(10) 0.0547(11) 0.0021(8) 0.0055(8) -0.0045(8) B3 0.0602(13) 0.0283(10) 0.0429(11) 0.0010(8) 0.0100(9) 0.0025(9) B4 0.0411(10) 0.0301(10) 0.0409(10) 0.0017(8) 0.0039(8) -0.0038(8) B5 0.0739(16) 0.0382(12) 0.0425(11) 0.0033(9) -0.0074(11) 0.0063(11) B6 0.0590(14) 0.0368(11) 0.0584(14) -0.0005(10) -0.0114(11) 0.0110(10) B7 0.0570(14) 0.0549(14) 0.0570(14) -0.0151(11) -0.0157(11) 0.0093(11) B8 0.0401(12) 0.0569(14) 0.0731(16) -0.0183(12) -0.0049(11) 0.0000(10) B9 0.0751(17) 0.0376(12) 0.0671(15) -0.0034(11) 0.0273(13) -0.0161(11) B10 0.109(2) 0.0289(11) 0.0591(15) 0.0068(10) 0.0148(14) -0.0028(12) B11 0.0657(15) 0.0299(11) 0.0593(14) -0.0046(9) 0.0022(11) -0.0022(10) B12 0.0625(15) 0.0489(14) 0.097(2) -0.0233(14) 0.0189(14) -0.0229(12) B23 0.0427(11) 0.0413(11) 0.0475(11) 0.0018(9) 0.0035(9) -0.0038(9) B24 0.0390(10) 0.0316(10) 0.0433(10) -0.0049(8) 0.0036(8) -0.0017(8) B25 0.0449(12) 0.0391(11) 0.0561(13) 0.0007(9) -0.0042(10) -0.0038(9) B26 0.0400(11) 0.0381(11) 0.0677(14) -0.0019(10) 0.0018(10) -0.0058(9) B27 0.0480(12) 0.0398(12) 0.0716(15) 0.0083(11) 0.0039(11) 0.0049(9) B28 0.0429(11) 0.0354(11) 0.0601(13) -0.0029(9) 0.0091(9) 0.0036(9) B29 0.0581(13) 0.0400(11) 0.0481(12) -0.0110(9) 0.0054(10) -0.0048(10) B30 0.0616(14) 0.0414(12) 0.0620(14) -0.0126(10) -0.0006(11) -0.0116(11) B31 0.0563(14) 0.0294(11) 0.0755(16) -0.0037(10) 0.0073(12) -0.0049(9) B32 0.0643(15) 0.0317(11) 0.0744(16) -0.0116(10) 0.0155(12) 0.0007(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 C2 C1 B3 60.40(12) . . ? C2 C1 B5 110.02(15) . . ? B3 C1 B5 111.31(16) . . ? C2 C1 B6 60.58(12) . . ? B3 C1 B6 111.34(16) . . ? B5 C1 B6 62.38(13) . . ? C2 C1 B4 110.41(15) . . ? B3 C1 B4 61.09(12) . . ? B5 C1 B4 62.71(12) . . ? B6 C1 B4 114.05(16) . . ? C11 C2 C1 117.25(17) . . ? C11 C2 B3 116.91(16) . . ? C1 C2 B3 60.64(12) . . ? C11 C2 B11 122.14(17) . . ? C1 C2 B11 111.81(15) . . ? B3 C2 B11 112.71(15) . . ? C11 C2 B7 119.94(18) . . ? C1 C2 B7 111.50(15) . . ? B3 C2 B7 61.89(13) . . ? B11 C2 B7 62.61(14) . . ? C11 C2 B6 118.79(18) . . ? C1 C2 B6 61.41(12) . . ? B3 C2 B6 112.23(15) . . ? B11 C2 B6 62.67(13) . . ? B7 C2 B6 114.14(17) . . ? C13 C12 C17 116.48(16) . . ? C13 C12 B4 117.04(15) . . ? C17 C12 B4 126.41(15) . . ? C14 C13 C12 121.80(17) . . ? C15 C14 C13 120.27(17) . . ? C14 C15 C16 121.80(17) . . ? C15 C16 C17 116.28(16) . . ? C15 C16 B24 116.11(15) . . ? C17 C16 B24 127.60(15) . . ? C12 C17 C16 123.35(15) . . ? C12 C17 C18 118.66(15) . . ? C16 C17 C18 117.99(15) . . ? N1 C18 C17 179.0(3) . . ? C22 C21 B25 111.83(15) . . ? C22 C21 B23 61.84(12) . . ? B25 C21 B23 114.28(15) . . ? C22 C21 B26 61.64(12) . . ? B25 C21 B26 62.71(13) . . ? B23 C21 B26 114.62(15) . . ? C22 C21 B24 112.47(14) . . ? B25 C21 B24 63.08(12) . . ? B23 C21 B24 62.49(12) . . ? B26 C21 B24 115.42(15) . . ? C19 C22 C21 117.61(17) . . ? C19 C22 B31 122.56(17) . . ? C21 C22 B31 110.11(16) . . ? C19 C22 B27 121.72(19) . . ? C21 C22 B27 110.18(15) . . ? B31 C22 B27 62.89(14) . . ? C19 C22 B26 117.27(18) . . ? C21 C22 B26 60.97(12) . . ? B31 C22 B26 62.15(13) . . ? B27 C22 B26 114.00(17) . . ? C19 C22 B23 116.74(17) . . ? C21 C22 B23 60.69(11) . . ? B31 C22 B23 113.42(16) . . ? B27 C22 B23 61.99(13) . . ? B26 C22 B23 113.09(15) . . ? C2 B3 C1 58.97(12) . . ? C2 B3 B8 107.79(15) . . ? C1 B3 B8 108.97(16) . . ? C2 B3 B4 108.99(15) . . ? C1 B3 B4 60.76(12) . . ? B8 B3 B4 62.19(13) . . ? C2 B3 B7 59.55(12) . . ? C1 B3 B7 108.23(15) . . ? B8 B3 B7 61.22(14) . . ? B4 B3 B7 112.17(16) . . ? C12 B4 C1 124.93(15) . . ? C12 B4 B3 121.64(15) . . ? C1 B4 B3 58.16(12) . . ? C12 B4 B9 124.96(16) . . ? C1 B4 B9 103.23(15) . . ? B3 B4 B9 104.87(15) . . ? C12 B4 B5 124.88(15) . . ? C1 B4 B5 57.76(12) . . ? B3 B4 B5 105.01(14) . . ? B9 B4 B5 59.02(14) . . ? C12 B4 B8 121.58(16) . . ? C1 B4 B8 104.06(15) . . ? B3 B4 B8 58.48(13) . . ? B9 B4 B8 59.72(15) . . ? B5 B4 B8 106.59(15) . . ? C1 B5 B9 105.68(17) . . ? C1 B5 B6 59.27(12) . . ? B9 B5 B6 107.56(17) . . ? C1 B5 B10 105.19(16) . . ? B9 B5 B10 60.04(15) . . ? B6 B5 B10 59.21(15) . . ? C1 B5 B4 59.53(12) . . ? B9 B5 B4 60.43(13) . . ? B6 B5 B4 108.92(15) . . ? B10 B5 B4 108.73(17) . . ? C2 B6 C1 58.01(12) . . ? C2 B6 B10 104.83(17) . . ? C1 B6 B10 105.55(17) . . ? C2 B6 B11 58.37(12) . . ? C1 B6 B11 105.63(16) . . ? B10 B6 B11 60.24(15) . . ? C2 B6 B5 104.80(15) . . ? C1 B6 B5 58.35(12) . . ? B10 B6 B5 60.58(14) . . ? B11 B6 B5 108.51(17) . . ? C2 B7 B3 58.56(12) . . ? C2 B7 B12 104.67(17) . . ? B3 B7 B12 106.31(17) . . ? C2 B7 B8 105.21(15) . . ? B3 B7 B8 58.92(13) . . ? B12 B7 B8 60.51(15) . . ? C2 B7 B11 58.48(12) . . ? B3 B7 B11 106.69(16) . . ? B12 B7 B11 60.01(15) . . ? B8 B7 B11 108.63(18) . . ? B3 B8 B7 59.86(13) . . ? B3 B8 B12 106.43(17) . . ? B7 B8 B12 59.73(15) . . ? B3 B8 B9 105.77(17) . . ? B7 B8 B9 107.49(18) . . ? B12 B8 B9 59.83(16) . . ? B3 B8 B4 59.32(12) . . ? B7 B8 B4 108.75(16) . . ? B12 B8 B4 108.50(18) . . ? B9 B8 B4 60.05(13) . . ? B5 B9 B10 60.47(15) . . ? B5 B9 B12 108.26(18) . . ? B10 B9 B12 59.70(16) . . ? B5 B9 B8 108.22(16) . . ? B10 B9 B8 107.89(18) . . ? B12 B9 B8 60.03(16) . . ? B5 B9 B4 60.56(12) . . ? B10 B9 B4 109.17(17) . . ? B12 B9 B4 108.81(18) . . ? B8 B9 B4 60.23(13) . . ? B6 B10 B12 108.28(18) . . ? B6 B10 B11 60.28(14) . . ? B12 B10 B11 59.96(15) . . ? B6 B10 B9 107.93(16) . . ? B12 B10 B9 60.26(16) . . ? B11 B10 B9 108.12(19) . . ? B6 B10 B5 60.21(14) . . ? B12 B10 B5 107.93(17) . . ? B11 B10 B5 108.25(16) . . ? B9 B10 B5 59.50(14) . . ? C2 B11 B7 58.91(13) . . ? C2 B11 B12 104.98(16) . . ? B7 B11 B12 59.98(16) . . ? C2 B11 B10 104.70(15) . . ? B7 B11 B10 107.86(17) . . ? B12 B11 B10 59.95(17) . . ? C2 B11 B6 58.96(12) . . ? B7 B11 B6 108.09(15) . . ? B12 B11 B6 107.63(17) . . ? B10 B11 B6 59.48(15) . . ? B7 B12 B10 107.99(18) . . ? B7 B12 B11 60.01(14) . . ? B10 B12 B11 60.09(16) . . ? B7 B12 B9 107.77(17) . . ? B10 B12 B9 60.03(16) . . ? B11 B12 B9 108.03(19) . . ? B7 B12 B8 59.76(15) . . ? B10 B12 B8 108.24(17) . . ? B11 B12 B8 108.03(17) . . ? B9 B12 B8 60.14(15) . . ? C21 B23 C22 57.47(11) . . ? C21 B23 B28 105.49(15) . . ? C22 B23 B28 105.67(15) . . ? C21 B23 B27 104.85(15) . . ? C22 B23 B27 58.53(12) . . ? B28 B23 B27 60.58(13) . . ? C21 B23 B24 59.13(11) . . ? C22 B23 B24 106.24(15) . . ? B28 B23 B24 60.96(12) . . ? B27 B23 B24 109.57(16) . . ? C16 B24 C21 126.75(15) . . ? C16 B24 B23 121.76(15) . . ? C21 B24 B23 58.38(11) . . ? C16 B24 B29 122.86(16) . . ? C21 B24 B29 103.19(14) . . ? B23 B24 B29 106.39(15) . . ? C16 B24 B25 123.52(16) . . ? C21 B24 B25 57.89(12) . . ? B23 B24 B25 106.68(14) . . ? B29 B24 B25 59.52(12) . . ? C16 B24 B28 121.49(15) . . ? C21 B24 B28 103.32(14) . . ? B23 B24 B28 58.88(12) . . ? B29 B24 B28 59.80(12) . . ? B25 B24 B28 107.05(14) . . ? C21 B25 B29 104.53(15) . . ? C21 B25 B26 59.02(12) . . ? B29 B25 B26 108.03(16) . . ? C21 B25 B30 104.74(16) . . ? B29 B25 B30 60.50(13) . . ? B26 B25 B30 59.59(13) . . ? C21 B25 B24 59.03(11) . . ? B29 B25 B24 60.15(12) . . ? B26 B25 B24 109.02(16) . . ? B30 B25 B24 109.11(16) . . ? C21 B26 C22 57.40(11) . . ? C21 B26 B30 104.72(15) . . ? C22 B26 B30 105.17(16) . . ? C21 B26 B31 104.30(15) . . ? C22 B26 B31 58.39(13) . . ? B30 B26 B31 60.23(14) . . ? C21 B26 B25 58.28(12) . . ? C22 B26 B25 104.89(15) . . ? B30 B26 B25 60.30(13) . . ? B31 B26 B25 108.01(16) . . ? C22 B27 B23 59.47(12) . . ? C22 B27 B32 104.79(17) . . ? B23 B27 B32 107.37(16) . . ? C22 B27 B28 105.41(15) . . ? B23 B27 B28 59.32(12) . . ? B32 B27 B28 60.30(13) . . ? C22 B27 B31 58.44(12) . . ? B23 B27 B31 107.77(16) . . ? B32 B27 B31 59.79(15) . . ? B28 B27 B31 108.11(17) . . ? B23 B28 B27 60.11(13) . . ? B23 B28 B29 107.50(15) . . ? B27 B28 B29 107.67(16) . . ? B23 B28 B32 107.58(16) . . ? B27 B28 B32 59.77(14) . . ? B29 B28 B32 59.78(14) . . ? B23 B28 B24 60.16(12) . . ? B27 B28 B24 108.56(15) . . ? B29 B28 B24 59.93(12) . . ? B32 B28 B24 108.07(16) . . ? B25 B29 B32 107.80(16) . . ? B25 B29 B28 108.06(15) . . ? B32 B29 B28 60.12(14) . . ? B25 B29 B24 60.33(12) . . ? B32 B29 B24 108.61(16) . . ? B28 B29 B24 60.27(12) . . ? B25 B29 B30 59.87(13) . . ? B32 B29 B30 60.07(14) . . ? B28 B29 B30 108.33(17) . . ? B24 B29 B30 108.75(16) . . ? B26 B30 B31 59.98(13) . . ? B26 B30 B25 60.10(13) . . ? B31 B30 B25 107.65(16) . . ? B26 B30 B32 107.65(18) . . ? B31 B30 B32 59.69(14) . . ? B25 B30 B32 107.24(16) . . ? B26 B30 B29 107.73(15) . . ? B31 B30 B29 107.35(17) . . ? B25 B30 B29 59.62(13) . . ? B32 B30 B29 59.61(14) . . ? C22 B31 B26 59.46(12) . . ? C22 B31 B32 105.07(16) . . ? B26 B31 B32 108.13(17) . . ? C22 B31 B30 105.65(15) . . ? B26 B31 B30 59.79(14) . . ? B32 B31 B30 60.48(15) . . ? C22 B31 B27 58.67(13) . . ? B26 B31 B27 108.36(15) . . ? B32 B31 B27 59.92(14) . . ? B30 B31 B27 108.54(17) . . ? B31 B32 B27 60.29(14) . . ? B31 B32 B29 108.03(16) . . ? B27 B32 B29 108.06(16) . . ? B31 B32 B28 108.22(16) . . ? B27 B32 B28 59.93(13) . . ? B29 B32 B28 60.10(13) . . ? B31 B32 B30 59.83(14) . . ? B27 B32 B30 108.31(16) . . ? B29 B32 B30 60.33(14) . . ? B28 B32 B30 108.52(16) . . ? 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 1.140(3) . ? C1 C2 1.659(3) . ? C1 B3 1.687(3) . ? C1 B5 1.701(3) . ? C1 B6 1.717(3) . ? C1 B4 1.733(3) . ? C2 C11 1.520(3) . ? C2 B3 1.683(3) . ? C2 B11 1.693(3) . ? C2 B7 1.701(3) . ? C2 B6 1.703(3) . ? C12 C13 1.393(2) . ? C12 C17 1.407(2) . ? C12 B4 1.586(3) . ? C13 C14 1.379(3) . ? C14 C15 1.376(3) . ? C15 C16 1.396(2) . ? C16 C17 1.415(2) . ? C16 B24 1.588(2) . ? C17 C18 1.441(2) . ? C19 C22 1.516(3) . ? C21 C22 1.647(3) . ? C21 B25 1.696(3) . ? C21 B23 1.703(3) . ? C21 B26 1.709(3) . ? C21 B24 1.716(3) . ? C22 B31 1.701(3) . ? C22 B27 1.705(3) . ? C22 B26 1.720(3) . ? C22 B23 1.722(3) . ? B3 B8 1.723(3) . ? B3 B4 1.738(3) . ? B3 B7 1.740(3) . ? B4 B9 1.785(3) . ? B4 B5 1.787(3) . ? B4 B8 1.788(3) . ? B5 B9 1.759(4) . ? B5 B6 1.770(3) . ? B5 B10 1.777(3) . ? B6 B10 1.752(4) . ? B6 B11 1.766(3) . ? B7 B12 1.763(4) . ? B7 B8 1.763(3) . ? B7 B11 1.763(3) . ? B8 B12 1.777(4) . ? B8 B9 1.779(4) . ? B9 B10 1.769(4) . ? B9 B12 1.773(4) . ? B10 B12 1.763(5) . ? B10 B11 1.766(4) . ? B11 B12 1.763(4) . ? B23 B28 1.750(3) . ? B23 B27 1.765(3) . ? B23 B24 1.774(3) . ? B24 B29 1.782(3) . ? B24 B25 1.785(3) . ? B24 B28 1.788(3) . ? B25 B29 1.770(3) . ? B25 B26 1.771(3) . ? B25 B30 1.775(3) . ? B26 B30 1.762(3) . ? B26 B31 1.766(3) . ? B27 B32 1.770(4) . ? B27 B28 1.773(3) . ? B27 B31 1.776(3) . ? B28 B29 1.779(3) . ? B28 B32 1.779(3) . ? B29 B32 1.773(3) . ? B29 B30 1.786(3) . ? B30 B31 1.770(4) . ? B30 B32 1.782(4) . ? B31 B32 1.768(3) . ?