#------------------------------------------------------------------------------ #$Date: 2020-05-16 04:10:18 +0300 (Sat, 16 May 2020) $ #$Revision: 252064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126539.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_7126539 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 'C18 H34 B20 N2' _chemical_formula_weight 494.67 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -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 85.6539(17) _cell_angle_beta 71.2257(14) _cell_angle_gamma 82.6628(11) _cell_formula_units_Z 2 _cell_length_a 11.1641(3) _cell_length_b 11.5247(3) _cell_length_c 12.2762(5) _cell_measurement_reflns_used 68 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 15 _cell_measurement_theta_min 15 _cell_volume 1482.20(8) _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 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 0.0475 _diffrn_reflns_av_unetI/netI 0.0402 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 23235 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.248 _diffrn_reflns_theta_min 1.753 _exptl_absorpt_coefficient_mu 0.054 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.4172 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.108 _exptl_crystal_description block _exptl_crystal_F_000 512 _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.858 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 361 _refine_ls_number_reflns 5369 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.1097 _refine_ls_R_factor_gt 0.0748 _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^)+(0.1384P)^2^+0.5259P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2206 _refine_ls_wR_factor_ref 0.2502 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3557 _reflns_number_total 5369 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc02531c2.cif _cod_data_source_block 3ay _cod_original_cell_volume 1482.19(8) _cod_database_code 7126539 _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 0.974 _shelx_estimated_absorpt_t_max 0.989 _shelxl_version_number 2014/6 _shelx_res_file ; TITL P in P-1 CELL 0.71073 11.16407 11.52468 12.27619 85.6539 71.2257 82.6628 ZERR 2.00 0.00028 0.00028 0.00049 0.0017 0.0014 0.0011 LATT 1 SFAC C H B N UNIT 36 68 40 4 REM C18 H34 B20 N2 REM APEXII BLOCK ORANGE OMIT -3 50.5 SIZE 0.50 0.30 0.20 L.S. 4 ACTA FMAP 2 PLAN 20 TEMP 23.000 WGHT 0.138400 0.525900 FVAR 0.24976 N1 4 0.386689 0.583984 0.256722 11.00000 0.04425 0.04566 = 0.04713 -0.00259 -0.01607 -0.00001 N2 4 0.452556 0.574323 0.156494 11.00000 0.05214 0.06544 = 0.04517 -0.00285 -0.01668 -0.01605 C1 1 0.692610 0.324408 0.280531 11.00000 0.07438 0.07404 = 0.09308 -0.00666 -0.04754 0.02084 C2 1 0.553423 0.399673 0.343264 11.00000 0.08657 0.06262 = 0.08530 -0.01050 -0.05558 0.01765 AFIX 153 H2 2 0.542823 0.495965 0.340451 11.00000 -1.20000 AFIX 0 C11 1 0.803164 0.393625 0.214654 11.00000 0.07206 0.13247 = 0.18678 0.01755 -0.06496 -0.00103 AFIX 33 H11A 2 0.877904 0.340433 0.182558 11.00000 -1.50000 H11B 2 0.782057 0.440122 0.153777 11.00000 -1.50000 H11C 2 0.819137 0.443898 0.266150 11.00000 -1.50000 AFIX 0 C12 1 0.300058 0.396652 0.324972 11.00000 0.06121 0.04486 = 0.04131 0.00051 -0.01851 -0.00488 C13 1 0.280054 0.515579 0.291311 11.00000 0.04402 0.04515 = 0.03761 0.00191 -0.01551 -0.00477 C14 1 0.161157 0.574099 0.295693 11.00000 0.04353 0.05081 = 0.04470 0.00307 -0.01488 -0.00607 C15 1 0.059047 0.506801 0.330606 11.00000 0.04736 0.06640 = 0.06901 0.01002 -0.01638 -0.01225 AFIX 43 H15A 2 -0.021653 0.541893 0.333522 11.00000 -1.20000 AFIX 0 C16 1 0.074777 0.389852 0.360816 11.00000 0.06360 0.06533 = 0.07541 0.01373 -0.01732 -0.02505 AFIX 43 H16A 2 0.005423 0.346590 0.382221 11.00000 -1.20000 AFIX 0 C17 1 0.192381 0.336780 0.359493 11.00000 0.07942 0.04849 = 0.05931 0.01110 -0.02079 -0.01521 AFIX 43 H17A 2 0.200516 0.258174 0.382414 11.00000 -1.20000 AFIX 0 C18 1 0.559498 0.640249 0.121460 11.00000 0.04591 0.05464 = 0.04646 0.00208 -0.01974 -0.00957 C19 1 0.637147 0.628881 0.009446 11.00000 0.06898 0.09767 = 0.04676 -0.00364 -0.01682 -0.02730 AFIX 43 H19A 2 0.617313 0.581770 -0.039171 11.00000 -1.20000 AFIX 0 C20 1 0.744141 0.687015 -0.030945 11.00000 0.06618 0.13543 = 0.05660 0.01302 -0.00885 -0.03482 AFIX 43 H20A 2 0.796968 0.678942 -0.106564 11.00000 -1.20000 AFIX 0 C21 1 0.772612 0.757554 0.041676 11.00000 0.06824 0.11194 = 0.08603 0.02810 -0.03415 -0.04532 AFIX 43 H21A 2 0.844364 0.797589 0.014495 11.00000 -1.20000 AFIX 0 C22 1 0.695656 0.768684 0.153345 11.00000 0.07987 0.08542 = 0.08150 0.00111 -0.03698 -0.03553 AFIX 43 H22A 2 0.715833 0.815600 0.201907 11.00000 -1.20000 AFIX 0 C23 1 0.589101 0.711028 0.193832 11.00000 0.05695 0.06852 = 0.05694 -0.00453 -0.02306 -0.01137 AFIX 43 H23A 2 0.536668 0.719210 0.269571 11.00000 -1.20000 AFIX 0 C24 1 0.349420 0.971107 0.101272 11.00000 0.09851 0.09531 = 0.17953 0.03501 -0.01426 -0.02087 AFIX 33 H24A 2 0.334635 1.033998 0.049633 11.00000 -1.50000 H24B 2 0.381536 1.000237 0.156449 11.00000 -1.50000 H24C 2 0.410509 0.911308 0.058327 11.00000 -1.50000 AFIX 0 C31 1 0.224252 0.919677 0.164172 11.00000 0.05877 0.05611 = 0.10948 0.02567 -0.01352 -0.00124 C32 1 0.233585 0.810501 0.256275 11.00000 0.04931 0.04616 = 0.08962 0.01426 -0.02250 -0.00057 AFIX 153 H32 2 0.325857 0.777773 0.267807 11.00000 -1.20000 AFIX 0 B3 3 0.573615 0.326517 0.224617 11.00000 0.06182 0.05748 = 0.05825 -0.00489 -0.02932 0.01208 AFIX 153 H3 2 0.576557 0.371803 0.141782 11.00000 -1.20000 AFIX 0 B4 3 0.671329 0.197881 0.227899 11.00000 0.10258 0.08170 = 0.06653 -0.02682 -0.03603 0.04347 AFIX 153 H4 2 0.737355 0.156877 0.149836 11.00000 -1.20000 AFIX 0 B5 3 0.712134 0.196443 0.355425 11.00000 0.11476 0.07825 = 0.08493 -0.02047 -0.05642 0.04908 AFIX 153 H5 2 0.804679 0.155110 0.360558 11.00000 -1.20000 AFIX 0 B6 3 0.636767 0.324632 0.428490 11.00000 0.12576 0.08616 = 0.09279 -0.03617 -0.08041 0.04832 AFIX 153 H6 2 0.679657 0.367202 0.481865 11.00000 -1.20000 AFIX 0 B7 3 0.429060 0.329942 0.334928 11.00000 0.07455 0.04268 = 0.04582 -0.00357 -0.02626 0.00445 B8 3 0.506850 0.198114 0.263614 11.00000 0.10180 0.05260 = 0.07110 -0.02069 -0.04230 0.00961 AFIX 153 H8 2 0.464712 0.156425 0.209059 11.00000 -1.20000 AFIX 0 B9 3 0.590918 0.114741 0.348409 11.00000 0.13125 0.04929 = 0.08651 -0.01411 -0.04190 0.03398 AFIX 153 H9 2 0.603195 0.018454 0.350329 11.00000 -1.20000 AFIX 0 B10 3 0.569498 0.193858 0.472283 11.00000 0.13829 0.07948 = 0.06149 -0.00490 -0.04552 0.05251 AFIX 153 H10 2 0.568053 0.149380 0.555133 11.00000 -1.20000 AFIX 0 B11 3 0.470947 0.324373 0.463944 11.00000 0.11208 0.06593 = 0.04925 -0.01728 -0.03940 0.03668 AFIX 153 H11 2 0.404945 0.366430 0.541419 11.00000 -1.20000 AFIX 0 B12 3 0.441695 0.194552 0.415936 11.00000 0.11094 0.04891 = 0.07114 0.00465 -0.03177 0.01523 AFIX 153 H12 2 0.356933 0.150278 0.461863 11.00000 -1.20000 AFIX 0 B33 3 0.164632 0.944732 0.305108 11.00000 0.06940 0.05273 = 0.10189 0.01091 -0.02877 0.00100 AFIX 153 H33 2 0.205610 1.002102 0.348069 11.00000 -1.20000 AFIX 0 B34 3 0.080732 1.001464 0.211674 11.00000 0.06575 0.05769 = 0.07412 0.01447 -0.00988 0.01259 AFIX 153 H34 2 0.064671 1.096000 0.193083 11.00000 -1.20000 AFIX 0 B35 3 0.111077 0.900298 0.105089 11.00000 0.09611 0.07497 = 0.04741 0.00975 -0.01628 0.02661 AFIX 153 H35 2 0.115770 0.928760 0.016372 11.00000 -1.20000 AFIX 0 B36 3 0.210774 0.779561 0.133761 11.00000 0.06230 0.06374 = 0.05463 0.01439 -0.00111 0.01724 AFIX 153 H36 2 0.281363 0.729508 0.064099 11.00000 -1.20000 AFIX 0 B37 3 0.103359 0.814862 0.373164 11.00000 0.07103 0.05689 = 0.05513 0.00736 -0.02892 0.00124 AFIX 153 H37 2 0.103349 0.787627 0.461005 11.00000 -1.20000 AFIX 0 B38 3 0.001009 0.935498 0.344871 11.00000 0.06635 0.06340 = 0.05715 -0.00199 -0.01477 0.01148 AFIX 153 H38 2 -0.067794 0.986790 0.414621 11.00000 -1.20000 AFIX 0 B39 3 -0.034270 0.907626 0.220456 11.00000 0.05616 0.07090 = 0.06857 -0.00443 -0.02780 0.01952 AFIX 153 H39 2 -0.126197 0.940110 0.208088 11.00000 -1.20000 AFIX 0 B40 3 0.047199 0.768542 0.171306 11.00000 0.07354 0.07138 = 0.06228 -0.01303 -0.03748 0.01909 AFIX 153 H40 2 0.008366 0.711136 0.126506 11.00000 -1.20000 AFIX 0 B41 3 0.131830 0.708807 0.266963 11.00000 0.04046 0.05582 = 0.04535 0.00619 -0.01495 -0.00086 B42 3 -0.020171 0.791367 0.320860 11.00000 0.04437 0.06693 = 0.05838 0.00155 -0.01001 -0.00048 AFIX 153 H42 2 -0.103300 0.748803 0.374564 11.00000 -1.20000 AFIX 0 HKLF 4 REM P in P-1 REM R1 = 0.0748 for 3557 Fo > 4sig(Fo) and 0.1097 for all 5369 data REM 361 parameters refined using 0 restraints END WGHT 0.1382 0.5258 REM Highest difference peak 0.858, deepest hole -0.290, 1-sigma level 0.047 Q1 1 0.2435 1.0030 0.3182 11.00000 0.05 0.86 Q2 1 0.1260 0.9407 0.3388 11.00000 0.05 0.26 Q3 1 0.5801 0.3563 0.1977 11.00000 0.05 0.25 Q4 1 0.1651 0.9283 0.2427 11.00000 0.05 0.23 Q5 1 0.5270 0.3322 0.2584 11.00000 0.05 0.19 Q6 1 0.0661 0.8615 0.0829 11.00000 0.05 0.19 Q7 1 0.1893 0.8714 0.1152 11.00000 0.05 0.19 Q8 1 0.2133 0.7754 0.2006 11.00000 0.05 0.19 Q9 1 0.0359 0.8450 0.3565 11.00000 0.05 0.18 Q10 1 0.6329 0.2883 0.2354 11.00000 0.05 0.18 Q11 1 0.2215 0.5401 0.2604 11.00000 0.05 0.18 Q12 1 0.3078 0.7554 0.0816 11.00000 0.05 0.17 Q13 1 0.7721 0.2143 0.1401 11.00000 0.05 0.16 Q14 1 0.1104 1.1150 0.2055 11.00000 0.05 0.15 Q15 1 0.0644 0.9499 0.1676 11.00000 0.05 0.15 Q16 1 0.1530 0.6370 0.2789 11.00000 0.05 0.15 Q17 1 0.3743 0.3680 0.3204 11.00000 0.05 0.15 Q18 1 0.6966 0.2566 0.3014 11.00000 0.05 0.14 Q19 1 0.2975 0.4367 0.2983 11.00000 0.05 0.14 Q20 1 0.7096 0.3921 0.4388 11.00000 0.05 0.14 ; _shelx_res_checksum 67156 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.38669(19) 0.58398(16) 0.25672(17) 0.0457(5) Uani 1 1 d . . . . . N2 N 0.4526(2) 0.57432(19) 0.15649(18) 0.0530(6) Uani 1 1 d . . . . . C1 C 0.6926(3) 0.3244(3) 0.2805(3) 0.0779(10) Uani 1 1 d . . . . . C2 C 0.5534(3) 0.3997(3) 0.3433(3) 0.0732(9) Uani 1 1 d . . . . . H2 H 0.5428 0.4960 0.3405 0.088 Uiso 1 1 calc R U . . . C11 C 0.8032(4) 0.3936(4) 0.2147(5) 0.1268(18) Uani 1 1 d . . . . . H11A H 0.8779 0.3404 0.1826 0.190 Uiso 1 1 calc R U . . . H11B H 0.7821 0.4401 0.1538 0.190 Uiso 1 1 calc R U . . . H11C H 0.8191 0.4439 0.2662 0.190 Uiso 1 1 calc R U . . . C12 C 0.3001(2) 0.3967(2) 0.3250(2) 0.0488(6) Uani 1 1 d . . . . . C13 C 0.2801(2) 0.5156(2) 0.29131(19) 0.0418(6) Uani 1 1 d . . . . . C14 C 0.1612(2) 0.5741(2) 0.2957(2) 0.0463(6) Uani 1 1 d . . . . . C15 C 0.0590(3) 0.5068(2) 0.3306(2) 0.0615(8) Uani 1 1 d . . . . . H15A H -0.0217 0.5419 0.3335 0.074 Uiso 1 1 calc R U . . . C16 C 0.0748(3) 0.3899(3) 0.3608(3) 0.0685(9) Uani 1 1 d . . . . . H16A H 0.0054 0.3466 0.3822 0.082 Uiso 1 1 calc R U . . . C17 C 0.1924(3) 0.3368(2) 0.3595(2) 0.0626(8) Uani 1 1 d . . . . . H17A H 0.2005 0.2582 0.3824 0.075 Uiso 1 1 calc R U . . . C18 C 0.5595(2) 0.6402(2) 0.1215(2) 0.0476(6) Uani 1 1 d . . . . . C19 C 0.6371(3) 0.6289(3) 0.0094(2) 0.0698(9) Uani 1 1 d . . . . . H19A H 0.6173 0.5818 -0.0392 0.084 Uiso 1 1 calc R U . . . C20 C 0.7441(3) 0.6870(4) -0.0309(3) 0.0873(11) Uani 1 1 d . . . . . H20A H 0.7970 0.6789 -0.1066 0.105 Uiso 1 1 calc R U . . . C21 C 0.7726(3) 0.7576(3) 0.0417(3) 0.0848(11) Uani 1 1 d . . . . . H21A H 0.8444 0.7976 0.0145 0.102 Uiso 1 1 calc R U . . . C22 C 0.6957(3) 0.7687(3) 0.1533(3) 0.0773(10) Uani 1 1 d . . . . . H22A H 0.7158 0.8156 0.2019 0.093 Uiso 1 1 calc R U . . . C23 C 0.5891(3) 0.7110(2) 0.1938(3) 0.0591(7) Uani 1 1 d . . . . . H23A H 0.5367 0.7192 0.2696 0.071 Uiso 1 1 calc R U . . . C24 C 0.3494(4) 0.9711(4) 0.1013(5) 0.1328(19) Uani 1 1 d . . . . . H24A H 0.3346 1.0340 0.0496 0.199 Uiso 1 1 calc R U . . . H24B H 0.3815 1.0002 0.1564 0.199 Uiso 1 1 calc R U . . . H24C H 0.4105 0.9113 0.0583 0.199 Uiso 1 1 calc R U . . . C31 C 0.2243(3) 0.9197(3) 0.1642(3) 0.0799(11) Uani 1 1 d . . . . . C32 C 0.2336(3) 0.8105(2) 0.2563(3) 0.0629(8) Uani 1 1 d . . . . . H32 H 0.3259 0.7778 0.2678 0.075 Uiso 1 1 calc R U . . . B3 B 0.5736(3) 0.3265(3) 0.2246(3) 0.0582(8) Uani 1 1 d . . . . . H3 H 0.5766 0.3718 0.1418 0.070 Uiso 1 1 calc R U . . . B4 B 0.6713(4) 0.1979(4) 0.2279(4) 0.0849(13) Uani 1 1 d . . . . . H4 H 0.7374 0.1569 0.1498 0.102 Uiso 1 1 calc R U . . . B5 B 0.7121(5) 0.1964(4) 0.3554(4) 0.0912(14) Uani 1 1 d . . . . . H5 H 0.8047 0.1551 0.3606 0.109 Uiso 1 1 calc R U . . . B6 B 0.6368(5) 0.3246(4) 0.4285(4) 0.0942(15) Uani 1 1 d . . . . . H6 H 0.6797 0.3672 0.4819 0.113 Uiso 1 1 calc R U . . . B7 B 0.4291(3) 0.3299(2) 0.3349(3) 0.0535(8) Uani 1 1 d . . . . . B8 B 0.5069(4) 0.1981(3) 0.2636(3) 0.0722(10) Uani 1 1 d . . . . . H8 H 0.4647 0.1564 0.2091 0.087 Uiso 1 1 calc R U . . . B9 B 0.5909(5) 0.1147(3) 0.3484(4) 0.0906(14) Uani 1 1 d . . . . . H9 H 0.6032 0.0185 0.3503 0.109 Uiso 1 1 calc R U . . . B10 B 0.5695(5) 0.1939(4) 0.4723(3) 0.0955(15) Uani 1 1 d . . . . . H10 H 0.5681 0.1494 0.5551 0.115 Uiso 1 1 calc R U . . . B11 B 0.4709(4) 0.3244(3) 0.4639(3) 0.0758(12) Uani 1 1 d . . . . . H11 H 0.4049 0.3664 0.5414 0.091 Uiso 1 1 calc R U . . . B12 B 0.4417(4) 0.1946(3) 0.4159(3) 0.0788(12) Uani 1 1 d . . . . . H12 H 0.3569 0.1503 0.4619 0.095 Uiso 1 1 calc R U . . . B33 B 0.1646(4) 0.9447(3) 0.3051(4) 0.0757(11) Uani 1 1 d . . . . . H33 H 0.2056 1.0021 0.3481 0.091 Uiso 1 1 calc R U . . . B34 B 0.0807(3) 1.0015(3) 0.2117(3) 0.0715(11) Uani 1 1 d . . . . . H34 H 0.0647 1.0960 0.1931 0.086 Uiso 1 1 calc R U . . . B35 B 0.1111(4) 0.9003(3) 0.1051(3) 0.0783(12) Uani 1 1 d . . . . . H35 H 0.1158 0.9288 0.0164 0.094 Uiso 1 1 calc R U . . . B36 B 0.2108(3) 0.7796(3) 0.1338(3) 0.0675(10) Uani 1 1 d . . . . . H36 H 0.2814 0.7295 0.0641 0.081 Uiso 1 1 calc R U . . . B37 B 0.1034(3) 0.8149(3) 0.3732(3) 0.0601(9) Uani 1 1 d . . . . . H37 H 0.1033 0.7876 0.4610 0.072 Uiso 1 1 calc R U . . . B38 B 0.0010(3) 0.9355(3) 0.3449(3) 0.0651(9) Uani 1 1 d . . . . . H38 H -0.0678 0.9868 0.4146 0.078 Uiso 1 1 calc R U . . . B39 B -0.0343(3) 0.9076(3) 0.2205(3) 0.0656(9) Uani 1 1 d . . . . . H39 H -0.1262 0.9401 0.2081 0.079 Uiso 1 1 calc R U . . . B40 B 0.0472(3) 0.7685(3) 0.1713(3) 0.0671(10) Uani 1 1 d . . . . . H40 H 0.0084 0.7111 0.1265 0.081 Uiso 1 1 calc R U . . . B41 B 0.1318(3) 0.7088(3) 0.2670(2) 0.0477(7) Uani 1 1 d . . . . . B42 B -0.0202(3) 0.7914(3) 0.3209(3) 0.0588(8) Uani 1 1 d . . . . . H42 H -0.1033 0.7488 0.3746 0.071 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 0.0442(12) 0.0457(11) 0.0471(13) -0.0026(9) -0.0161(10) 0.0000(9) N2 0.0521(13) 0.0654(14) 0.0452(13) -0.0029(10) -0.0167(11) -0.0161(11) C1 0.074(2) 0.074(2) 0.093(2) -0.0067(17) -0.0475(19) 0.0208(17) C2 0.087(2) 0.0626(18) 0.085(2) -0.0105(15) -0.0556(19) 0.0176(16) C11 0.072(3) 0.132(4) 0.187(5) 0.018(3) -0.065(3) -0.001(2) C12 0.0612(16) 0.0449(13) 0.0413(14) 0.0005(10) -0.0185(12) -0.0049(12) C13 0.0440(14) 0.0451(13) 0.0376(13) 0.0019(9) -0.0155(10) -0.0048(10) C14 0.0435(14) 0.0508(14) 0.0447(14) 0.0031(10) -0.0149(11) -0.0061(11) C15 0.0474(16) 0.0664(18) 0.0690(19) 0.0100(14) -0.0164(14) -0.0123(13) C16 0.0636(19) 0.0653(18) 0.075(2) 0.0137(15) -0.0173(16) -0.0251(15) C17 0.079(2) 0.0485(15) 0.0593(17) 0.0111(12) -0.0208(15) -0.0152(14) C18 0.0459(14) 0.0546(14) 0.0465(15) 0.0021(11) -0.0197(12) -0.0096(11) C19 0.069(2) 0.098(2) 0.0468(16) -0.0036(15) -0.0168(14) -0.0273(17) C20 0.066(2) 0.135(3) 0.0566(19) 0.013(2) -0.0088(16) -0.035(2) C21 0.068(2) 0.112(3) 0.086(3) 0.028(2) -0.0342(19) -0.045(2) C22 0.080(2) 0.085(2) 0.081(2) 0.0011(17) -0.0370(19) -0.0355(19) C23 0.0570(17) 0.0685(18) 0.0569(17) -0.0045(13) -0.0231(14) -0.0114(14) C24 0.099(3) 0.095(3) 0.180(5) 0.035(3) -0.014(3) -0.021(2) C31 0.0588(19) 0.0561(17) 0.109(3) 0.0257(17) -0.0135(18) -0.0012(14) C32 0.0493(16) 0.0462(14) 0.090(2) 0.0143(14) -0.0225(15) -0.0006(12) B3 0.062(2) 0.0575(18) 0.0583(19) -0.0049(14) -0.0293(16) 0.0121(15) B4 0.103(3) 0.082(3) 0.067(2) -0.0268(19) -0.036(2) 0.043(2) B5 0.115(3) 0.078(3) 0.085(3) -0.020(2) -0.056(3) 0.049(2) B6 0.126(4) 0.086(3) 0.093(3) -0.036(2) -0.080(3) 0.048(3) B7 0.075(2) 0.0427(15) 0.0458(17) -0.0036(12) -0.0263(15) 0.0044(14) B8 0.102(3) 0.0526(19) 0.071(2) -0.0207(16) -0.042(2) 0.0096(18) B9 0.131(4) 0.049(2) 0.087(3) -0.0141(18) -0.042(3) 0.034(2) B10 0.138(4) 0.079(3) 0.061(2) -0.0049(19) -0.046(2) 0.053(3) B11 0.112(3) 0.066(2) 0.0492(19) -0.0173(15) -0.039(2) 0.037(2) B12 0.111(3) 0.0489(19) 0.071(2) 0.0046(16) -0.032(2) 0.0152(19) B33 0.069(2) 0.0527(19) 0.102(3) 0.0109(18) -0.029(2) 0.0010(16) B34 0.066(2) 0.0577(19) 0.074(2) 0.0145(17) -0.0099(18) 0.0126(16) B35 0.096(3) 0.075(2) 0.0474(19) 0.0098(16) -0.0163(19) 0.027(2) B36 0.062(2) 0.064(2) 0.055(2) 0.0144(15) -0.0011(16) 0.0172(16) B37 0.071(2) 0.0569(18) 0.0551(19) 0.0074(14) -0.0289(16) 0.0012(16) B38 0.066(2) 0.063(2) 0.057(2) -0.0020(15) -0.0148(17) 0.0115(16) B39 0.056(2) 0.071(2) 0.069(2) -0.0044(16) -0.0278(17) 0.0195(16) B40 0.074(2) 0.071(2) 0.062(2) -0.0130(16) -0.0375(18) 0.0191(18) B41 0.0405(16) 0.0558(17) 0.0453(16) 0.0062(12) -0.0150(13) -0.0009(12) B42 0.0444(17) 0.067(2) 0.0584(19) 0.0016(15) -0.0100(14) -0.0005(14) 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 N2 N1 C13 114.4(2) . . ? N1 N2 C18 115.0(2) . . ? C11 C1 C2 117.5(3) . . ? C11 C1 B3 117.1(3) . . ? C2 C1 B3 60.35(18) . . ? C11 C1 B5 122.7(3) . . ? C2 C1 B5 111.2(3) . . ? B3 C1 B5 111.9(3) . . ? C11 C1 B4 120.7(4) . . ? C2 C1 B4 110.5(3) . . ? B3 C1 B4 61.4(2) . . ? B5 C1 B4 62.2(2) . . ? C11 C1 B6 119.9(3) . . ? C2 C1 B6 61.6(2) . . ? B3 C1 B6 111.5(3) . . ? B5 C1 B6 61.8(2) . . ? B4 C1 B6 112.4(3) . . ? C1 C2 B3 60.4(2) . . ? C1 C2 B11 109.9(2) . . ? B3 C2 B11 110.8(2) . . ? C1 C2 B7 111.4(2) . . ? B3 C2 B7 61.51(19) . . ? B11 C2 B7 62.6(2) . . ? C1 C2 B6 61.0(2) . . ? B3 C2 B6 111.1(2) . . ? B11 C2 B6 61.5(2) . . ? B7 C2 B6 113.8(3) . . ? C17 C12 C13 115.5(2) . . ? C17 C12 B7 118.2(2) . . ? C13 C12 B7 126.1(2) . . ? C14 C13 C12 124.0(2) . . ? C14 C13 N1 117.1(2) . . ? C12 C13 N1 118.7(2) . . ? C15 C14 C13 116.3(2) . . ? C15 C14 B41 117.5(2) . . ? C13 C14 B41 126.2(2) . . ? C16 C15 C14 121.6(3) . . ? C17 C16 C15 120.2(3) . . ? C16 C17 C12 122.2(2) . . ? C19 C18 C23 119.8(2) . . ? C19 C18 N2 116.2(2) . . ? C23 C18 N2 124.0(2) . . ? C18 C19 C20 120.2(3) . . ? C19 C20 C21 119.6(3) . . ? C22 C21 C20 120.3(3) . . ? C21 C22 C23 120.3(3) . . ? C22 C23 C18 119.8(3) . . ? C24 C31 C32 115.5(3) . . ? C24 C31 B33 115.1(4) . . ? C32 C31 B33 61.6(2) . . ? C24 C31 B35 125.5(3) . . ? C32 C31 B35 109.0(2) . . ? B33 C31 B35 112.8(3) . . ? C24 C31 B34 123.9(3) . . ? C32 C31 B34 110.1(2) . . ? B33 C31 B34 62.2(2) . . ? B35 C31 B34 61.8(2) . . ? C24 C31 B36 117.9(3) . . ? C32 C31 B36 59.68(18) . . ? B33 C31 B36 112.5(2) . . ? B35 C31 B36 61.9(2) . . ? B34 C31 B36 112.5(3) . . ? C31 C32 B36 62.5(2) . . ? C31 C32 B37 111.9(2) . . ? B36 C32 B37 115.2(2) . . ? C31 C32 B33 60.1(2) . . ? B36 C32 B33 113.7(2) . . ? B37 C32 B33 62.9(2) . . ? C31 C32 B41 114.3(2) . . ? B36 C32 B41 63.59(18) . . ? B37 C32 B41 63.48(18) . . ? B33 C32 B41 115.8(2) . . ? C2 B3 C1 59.24(19) . . ? C2 B3 B8 109.1(2) . . ? C1 B3 B8 108.6(2) . . ? C2 B3 B4 108.7(2) . . ? C1 B3 B4 60.3(2) . . ? B8 B3 B4 61.0(2) . . ? C2 B3 B7 60.61(19) . . ? C1 B3 B7 109.7(2) . . ? B8 B3 B7 62.54(19) . . ? B4 B3 B7 112.5(3) . . ? C1 B4 B3 58.31(19) . . ? C1 B4 B8 105.3(2) . . ? B3 B4 B8 58.9(2) . . ? C1 B4 B9 105.6(3) . . ? B3 B4 B9 106.8(3) . . ? B8 B4 B9 60.9(3) . . ? C1 B4 B5 58.8(2) . . ? B3 B4 B5 106.7(3) . . ? B8 B4 B5 109.1(3) . . ? B9 B4 B5 60.5(3) . . ? C1 B5 B6 59.5(2) . . ? C1 B5 B4 59.1(2) . . ? B6 B5 B4 108.1(3) . . ? C1 B5 B10 105.0(3) . . ? B6 B5 B10 59.1(3) . . ? B4 B5 B10 107.2(3) . . ? C1 B5 B9 105.0(3) . . ? B6 B5 B9 107.3(3) . . ? B4 B5 B9 59.3(3) . . ? B10 B5 B9 59.9(3) . . ? C1 B6 C2 57.4(2) . . ? C1 B6 B10 105.6(3) . . ? C2 B6 B10 105.9(3) . . ? C1 B6 B5 58.7(2) . . ? C2 B6 B5 105.4(3) . . ? B10 B6 B5 60.7(3) . . ? C1 B6 B11 104.8(3) . . ? C2 B6 B11 58.7(2) . . ? B10 B6 B11 60.5(3) . . ? B5 B6 B11 108.7(3) . . ? C12 B7 C2 123.6(2) . . ? C12 B7 B3 124.0(2) . . ? C2 B7 B3 57.89(19) . . ? C12 B7 B11 122.6(2) . . ? C2 B7 B11 58.3(2) . . ? B3 B7 B11 104.6(2) . . ? C12 B7 B8 124.8(2) . . ? C2 B7 B8 103.4(2) . . ? B3 B7 B8 57.9(2) . . ? B11 B7 B8 105.4(2) . . ? C12 B7 B12 124.6(3) . . ? C2 B7 B12 103.4(2) . . ? B3 B7 B12 104.2(2) . . ? B11 B7 B12 58.6(2) . . ? B8 B7 B12 59.2(2) . . ? B3 B8 B4 60.1(2) . . ? B3 B8 B9 106.9(3) . . ? B4 B8 B9 59.7(2) . . ? B3 B8 B12 106.6(3) . . ? B4 B8 B12 108.0(3) . . ? B9 B8 B12 60.0(2) . . ? B3 B8 B7 59.57(19) . . ? B4 B8 B7 109.4(3) . . ? B9 B8 B7 109.3(3) . . ? B12 B8 B7 60.69(18) . . ? B4 B9 B10 108.0(3) . . ? B4 B9 B8 59.4(2) . . ? B10 B9 B8 107.9(2) . . ? B4 B9 B5 60.1(3) . . ? B10 B9 B5 60.0(3) . . ? B8 B9 B5 107.6(3) . . ? B4 B9 B12 107.8(3) . . ? B10 B9 B12 60.1(2) . . ? B8 B9 B12 60.1(2) . . ? B5 B9 B12 108.1(3) . . ? B6 B10 B11 60.3(2) . . ? B6 B10 B9 108.3(3) . . ? B11 B10 B9 107.6(3) . . ? B6 B10 B5 60.1(3) . . ? B11 B10 B5 108.1(3) . . ? B9 B10 B5 60.1(3) . . ? B6 B10 B12 108.1(3) . . ? B11 B10 B12 59.4(2) . . ? B9 B10 B12 60.1(2) . . ? B5 B10 B12 108.2(3) . . ? C2 B11 B12 106.0(2) . . ? C2 B11 B6 59.8(2) . . ? B12 B11 B6 108.2(3) . . ? C2 B11 B10 105.7(3) . . ? B12 B11 B10 60.6(2) . . ? B6 B11 B10 59.2(3) . . ? C2 B11 B7 59.07(18) . . ? B12 B11 B7 61.18(19) . . ? B6 B11 B7 109.4(3) . . ? B10 B11 B7 109.9(2) . . ? B11 B12 B9 107.7(3) . . ? B11 B12 B10 60.0(2) . . ? B9 B12 B10 59.8(2) . . ? B11 B12 B8 107.4(3) . . ? B9 B12 B8 59.9(2) . . ? B10 B12 B8 107.4(3) . . ? B11 B12 B7 60.26(18) . . ? B9 B12 B7 108.7(3) . . ? B10 B12 B7 108.7(3) . . ? B8 B12 B7 60.09(18) . . ? C31 B33 C32 58.3(2) . . ? C31 B33 B34 59.6(2) . . ? C32 B33 B34 105.6(3) . . ? C31 B33 B38 106.8(3) . . ? C32 B33 B38 104.9(3) . . ? B34 B33 B38 60.5(2) . . ? C31 B33 B37 106.4(3) . . ? C32 B33 B37 58.05(18) . . ? B34 B33 B37 109.0(3) . . ? B38 B33 B37 60.6(2) . . ? C31 B34 B35 58.8(2) . . ? C31 B34 B33 58.2(2) . . ? B35 B34 B33 107.1(3) . . ? C31 B34 B39 106.2(2) . . ? B35 B34 B39 61.0(2) . . ? B33 B34 B39 107.8(2) . . ? C31 B34 B38 105.2(2) . . ? B35 B34 B38 108.5(3) . . ? B33 B34 B38 59.9(2) . . ? B39 B34 B38 60.0(2) . . ? C31 B35 B34 59.4(2) . . ? C31 B35 B36 59.9(2) . . ? B34 B35 B36 108.9(3) . . ? C31 B35 B39 105.7(3) . . ? B34 B35 B39 59.9(2) . . ? B36 B35 B39 107.7(2) . . ? C31 B35 B40 105.8(2) . . ? B34 B35 B40 108.2(2) . . ? B36 B35 B40 59.31(19) . . ? B39 B35 B40 60.1(2) . . ? C32 B36 C31 57.9(2) . . ? C32 B36 B40 104.9(2) . . ? C31 B36 B40 106.0(2) . . ? C32 B36 B35 104.6(2) . . ? C31 B36 B35 58.2(2) . . ? B40 B36 B35 61.2(2) . . ? C32 B36 B41 58.99(17) . . ? C31 B36 B41 106.8(2) . . ? B40 B36 B41 60.53(18) . . ? B35 B36 B41 109.9(2) . . ? C32 B37 B42 104.6(2) . . ? C32 B37 B33 59.03(19) . . ? B42 B37 B33 107.4(2) . . ? C32 B37 B38 104.6(2) . . ? B42 B37 B38 60.15(19) . . ? B33 B37 B38 59.27(19) . . ? C32 B37 B41 58.88(18) . . ? B42 B37 B41 60.61(18) . . ? B33 B37 B41 108.8(2) . . ? B38 B37 B41 109.2(2) . . ? B33 B38 B39 107.5(3) . . ? B33 B38 B34 59.7(2) . . ? B39 B38 B34 59.9(2) . . ? B33 B38 B42 107.6(2) . . ? B39 B38 B42 60.6(2) . . ? B34 B38 B42 108.3(3) . . ? B33 B38 B37 60.16(19) . . ? B39 B38 B37 108.1(2) . . ? B34 B38 B37 108.0(2) . . ? B42 B38 B37 59.48(19) . . ? B34 B39 B38 60.1(2) . . ? B34 B39 B35 59.1(2) . . ? B38 B39 B35 107.1(3) . . ? B34 B39 B42 108.0(2) . . ? B38 B39 B42 60.0(2) . . ? B35 B39 B42 107.5(2) . . ? B34 B39 B40 107.8(2) . . ? B38 B39 B40 107.7(2) . . ? B35 B39 B40 60.3(2) . . ? B42 B39 B40 59.67(19) . . ? B36 B40 B42 107.6(3) . . ? B36 B40 B41 60.50(18) . . ? B42 B40 B41 60.29(18) . . ? B36 B40 B39 107.4(3) . . ? B42 B40 B39 59.99(19) . . ? B41 B40 B39 108.9(2) . . ? B36 B40 B35 59.5(2) . . ? B42 B40 B35 107.2(3) . . ? B41 B40 B35 108.4(3) . . ? B39 B40 B35 59.6(2) . . ? C14 B41 C32 124.0(2) . . ? C14 B41 B36 123.5(2) . . ? C32 B41 B36 57.42(19) . . ? C14 B41 B37 120.9(2) . . ? C32 B41 B37 57.63(18) . . ? B36 B41 B37 105.5(2) . . ? C14 B41 B40 125.9(2) . . ? C32 B41 B40 102.5(2) . . ? B36 B41 B40 58.97(19) . . ? B37 B41 B40 106.1(2) . . ? C14 B41 B42 124.5(2) . . ? C32 B41 B42 102.4(2) . . ? B36 B41 B42 105.9(2) . . ? B37 B41 B42 58.98(19) . . ? B40 B41 B42 59.61(18) . . ? B37 B42 B38 60.38(19) . . ? B37 B42 B40 107.7(2) . . ? B38 B42 B40 107.7(2) . . ? B37 B42 B39 107.8(2) . . ? B38 B42 B39 59.4(2) . . ? B40 B42 B39 60.33(19) . . ? B37 B42 B41 60.41(18) . . ? B38 B42 B41 109.2(2) . . ? B40 B42 B41 60.10(17) . . ? B39 B42 B41 109.0(2) . . ? 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 N2 1.218(3) . ? N1 C13 1.443(3) . ? N2 C18 1.428(3) . ? C1 C11 1.525(5) . ? C1 C2 1.657(4) . ? C1 B3 1.677(5) . ? C1 B5 1.706(5) . ? C1 B4 1.712(5) . ? C1 B6 1.720(6) . ? C2 B3 1.676(5) . ? C2 B11 1.711(5) . ? C2 B7 1.724(5) . ? C2 B6 1.730(5) . ? C12 C17 1.393(4) . ? C12 C13 1.412(3) . ? C12 B7 1.580(4) . ? C13 C14 1.397(3) . ? C14 C15 1.395(3) . ? C14 B41 1.582(4) . ? C15 C16 1.375(4) . ? C16 C17 1.371(4) . ? C18 C19 1.375(4) . ? C18 C23 1.390(4) . ? C19 C20 1.376(4) . ? C20 C21 1.384(5) . ? C21 C22 1.369(5) . ? C22 C23 1.369(4) . ? C24 C31 1.532(5) . ? C31 C32 1.643(4) . ? C31 B33 1.675(6) . ? C31 B35 1.691(6) . ? C31 B34 1.701(5) . ? C31 B36 1.720(5) . ? C32 B36 1.675(5) . ? C32 B37 1.681(4) . ? C32 B33 1.698(5) . ? C32 B41 1.704(4) . ? B3 B8 1.709(5) . ? B3 B4 1.731(5) . ? B3 B7 1.739(5) . ? B4 B8 1.745(6) . ? B4 B9 1.750(6) . ? B4 B5 1.764(6) . ? B5 B6 1.759(5) . ? B5 B10 1.769(7) . ? B5 B9 1.771(7) . ? B6 B10 1.741(7) . ? B6 B11 1.760(7) . ? B7 B11 1.785(5) . ? B7 B8 1.790(4) . ? B7 B12 1.801(4) . ? B8 B9 1.770(6) . ? B8 B12 1.774(6) . ? B9 B10 1.767(6) . ? B9 B12 1.773(6) . ? B10 B11 1.763(5) . ? B10 B12 1.774(7) . ? B11 B12 1.754(5) . ? B33 B34 1.744(6) . ? B33 B38 1.748(5) . ? B33 B37 1.764(5) . ? B34 B35 1.741(6) . ? B34 B39 1.754(5) . ? B34 B38 1.758(5) . ? B35 B36 1.755(5) . ? B35 B39 1.775(5) . ? B35 B40 1.786(5) . ? B36 B40 1.753(5) . ? B36 B41 1.780(4) . ? B37 B42 1.755(5) . ? B37 B38 1.771(5) . ? B37 B41 1.781(5) . ? B38 B39 1.756(5) . ? B38 B42 1.767(5) . ? B39 B42 1.778(5) . ? B39 B40 1.784(5) . ? B40 B42 1.772(5) . ? B40 B41 1.781(4) . ? B41 B42 1.784(4) . ?