Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Suning Wang' _publ_contact_author_address ; Department of Chemistry Queen's University Kingston Ontario K7L 3N6 CANADA ; _publ_contact_author_email WANGS@CHEM.QUEENSU.CA _publ_section_title ; Three-Coordinate Organoboron with a B=N Bond: Substituent Effect, Luminescence/Electroluminescence and Reactions with fluoride ; loop_ _publ_author_name 'Suning Wang' 'Yi Cui' 'Fenghong Li' 'Zheng-Hong Lu' data_bob _database_code_depnum_ccdc_archive 'CCDC 639173' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H29.33 B1.33 O0.67' _chemical_formula_weight 342.89 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.9762(13) _cell_length_b 8.5219(12) _cell_length_c 40.736(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.164(3) _cell_angle_gamma 90.00 _cell_volume 3111.3(8) _cell_formula_units_Z 6 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.098 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.680 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21312 _diffrn_reflns_av_R_equivalents 0.0620 _diffrn_reflns_av_sigmaI/netI 0.1079 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -53 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 28.30 _reflns_number_total 7319 _reflns_number_gt 2878 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7319 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2035 _refine_ls_R_factor_gt 0.0986 _refine_ls_wR_factor_ref 0.3560 _refine_ls_wR_factor_gt 0.3214 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4888(3) 0.6984(3) 0.12533(7) 0.0551(8) Uani 1 1 d . . . C2 C 0.8292(5) 0.6218(5) 0.14610(11) 0.0546(11) Uani 1 1 d . . . C3 C 0.7025(4) 0.6424(5) 0.16521(10) 0.0509(11) Uani 1 1 d . . . C4 C 0.6116(5) 0.9887(5) 0.18913(11) 0.0537(11) Uani 1 1 d . . . C5 C 0.5089(4) 0.8884(5) 0.17309(9) 0.0473(10) Uani 1 1 d . . . C6 C 0.3615(5) 0.8995(5) 0.18041(10) 0.0527(11) Uani 1 1 d . . . C7 C 0.1888(5) 0.5378(5) 0.07213(11) 0.0608(12) Uani 1 1 d . . . C8 C 0.4191(6) 1.0983(5) 0.22163(10) 0.0599(12) Uani 1 1 d . . . C9 C 0.3180(5) 1.0040(5) 0.20482(11) 0.0545(11) Uani 1 1 d . . . H9A H 0.2181 1.0092 0.2096 0.065 Uiso 1 1 calc R . . C10 C 0.3129(5) 0.5163(5) 0.09370(10) 0.0524(11) Uani 1 1 d . . . C11 C 0.7028(5) 0.5616(5) 0.19549(11) 0.0560(11) Uani 1 1 d . . . C12 C 0.3216(5) 0.3777(5) 0.11311(10) 0.0545(11) Uani 1 1 d . . . C13 C 0.5632(5) 1.0933(5) 0.21240(11) 0.0612(12) Uani 1 1 d . . . H13A H 0.6319 1.1631 0.2222 0.073 Uiso 1 1 calc R . . C14 C 0.5260(5) 0.7060(5) 0.06562(10) 0.0498(10) Uani 1 1 d . . . C15 C 0.9429(5) 0.5246(5) 0.15719(12) 0.0596(12) Uani 1 1 d . . . H15A H 1.0251 0.5137 0.1444 0.072 Uiso 1 1 calc R . . C16 C 0.5999(5) 0.6044(6) 0.04436(11) 0.0592(12) Uani 1 1 d . . . C17 C 0.5424(6) 0.8667(5) 0.06045(11) 0.0624(12) Uani 1 1 d . . . B2 B 0.4444(5) 0.6401(5) 0.09583(12) 0.0483(12) Uani 1 1 d . . . C19 C 0.8442(6) 0.7118(7) 0.11473(12) 0.0743(14) Uani 1 1 d . . . H19A H 0.9359 0.6833 0.1052 0.111 Uiso 1 1 calc R . . H19B H 0.8445 0.8223 0.1193 0.111 Uiso 1 1 calc R . . H19C H 0.7617 0.6873 0.0996 0.111 Uiso 1 1 calc R . . C20 C 0.6247(6) 0.9213(6) 0.03569(13) 0.0768(15) Uani 1 1 d . . . H20A H 0.6308 1.0292 0.0325 0.092 Uiso 1 1 calc R . . C21 C 0.8189(5) 0.4637(5) 0.20505(12) 0.0626(12) Uani 1 1 d . . . H21A H 0.8153 0.4096 0.2248 0.075 Uiso 1 1 calc R . . B1 B 0.5682(6) 0.7432(6) 0.15277(12) 0.0508(12) Uani 1 1 d . . . C23 C 0.2082(6) 0.2699(6) 0.11055(13) 0.0710(14) Uani 1 1 d . . . H23A H 0.2149 0.1797 0.1234 0.085 Uiso 1 1 calc R . . C24 C 0.9417(5) 0.4428(6) 0.18607(14) 0.0662(13) Uani 1 1 d . . . C25 C 0.0832(6) 0.2917(7) 0.08921(16) 0.0807(16) Uani 1 1 d . . . C26 C 0.1700(6) 0.6783(6) 0.05069(13) 0.0812(16) Uani 1 1 d . . . H26A H 0.2553 0.7455 0.0540 0.122 Uiso 1 1 calc R . . H26B H 0.0817 0.7342 0.0561 0.122 Uiso 1 1 calc R . . H26C H 0.1607 0.6460 0.0281 0.122 Uiso 1 1 calc R . . C27 C 0.6834(5) 0.6656(6) 0.02037(11) 0.0668(13) Uani 1 1 d . . . H27A H 0.7318 0.5964 0.0069 0.080 Uiso 1 1 calc R . . C28 C 0.0748(6) 0.4237(7) 0.07115(13) 0.0752(14) Uani 1 1 d . . . H28A H -0.0099 0.4406 0.0574 0.090 Uiso 1 1 calc R . . C29 C 0.5907(6) 0.4297(6) 0.04810(13) 0.0776(15) Uani 1 1 d . . . H29A H 0.6460 0.3799 0.0315 0.116 Uiso 1 1 calc R . . H29B H 0.4882 0.3973 0.0458 0.116 Uiso 1 1 calc R . . H29C H 0.6321 0.3999 0.0694 0.116 Uiso 1 1 calc R . . C30 C 0.5730(6) 0.5780(7) 0.21680(12) 0.0767(15) Uani 1 1 d . . . H30A H 0.5897 0.5151 0.2362 0.115 Uiso 1 1 calc R . . H30B H 0.4837 0.5435 0.2049 0.115 Uiso 1 1 calc R . . H30C H 0.5623 0.6860 0.2230 0.115 Uiso 1 1 calc R . . C31 C 0.4714(7) 0.9870(6) 0.08271(14) 0.0895(18) Uani 1 1 d . . . H31A H 0.4954 1.0910 0.0757 0.134 Uiso 1 1 calc R . . H31B H 0.5093 0.9719 0.1050 0.134 Uiso 1 1 calc R . . H31C H 0.3651 0.9735 0.0815 0.134 Uiso 1 1 calc R . . C32 C 0.2393(5) 0.8010(6) 0.16430(13) 0.0732(14) Uani 1 1 d . . . H32A H 0.2805 0.7334 0.1483 0.110 Uiso 1 1 calc R . . H32B H 0.1655 0.8682 0.1537 0.110 Uiso 1 1 calc R . . H32C H 0.1939 0.7387 0.1806 0.110 Uiso 1 1 calc R . . C33 C 0.4542(6) 0.3435(6) 0.13632(12) 0.0799(16) Uani 1 1 d . . . H33A H 0.4390 0.2456 0.1473 0.120 Uiso 1 1 calc R . . H33B H 0.4655 0.4260 0.1523 0.120 Uiso 1 1 calc R . . H33C H 0.5425 0.3370 0.1241 0.120 Uiso 1 1 calc R . . C34 C 0.6997(6) 0.8232(7) 0.01510(12) 0.0768(15) Uani 1 1 d . . . C35 C 0.3734(7) 1.2016(6) 0.24933(13) 0.0873(17) Uani 1 1 d . . . H35A H 0.2684 1.1895 0.2520 0.131 Uiso 1 1 calc R . . H35B H 0.3945 1.3091 0.2443 0.131 Uiso 1 1 calc R . . H35C H 0.4280 1.1719 0.2693 0.131 Uiso 1 1 calc R . . C36 C 1.0648(6) 0.3356(7) 0.19753(16) 0.0942(18) Uani 1 1 d . . . H36A H 1.1396 0.3336 0.1816 0.141 Uiso 1 1 calc R . . H36B H 1.0259 0.2318 0.2002 0.141 Uiso 1 1 calc R . . H36C H 1.1083 0.3724 0.2182 0.141 Uiso 1 1 calc R . . C37 C 0.7736(5) 0.9955(7) 0.18185(15) 0.0871(17) Uani 1 1 d . . . H37A H 0.8229 1.0737 0.1955 0.131 Uiso 1 1 calc R . . H37B H 0.7825 1.0221 0.1591 0.131 Uiso 1 1 calc R . . H37C H 0.8188 0.8951 0.1863 0.131 Uiso 1 1 calc R . . C38 C 0.7968(8) 0.8889(10) -0.01034(15) 0.119(2) Uani 1 1 d . . . H38A H 0.8395 0.8044 -0.0223 0.178 Uiso 1 1 calc R . . H38B H 0.8752 0.9504 0.0002 0.178 Uiso 1 1 calc R . . H38C H 0.7379 0.9539 -0.0253 0.178 Uiso 1 1 calc R . . C39 C -0.0396(7) 0.1696(9) 0.0877(2) 0.119(2) Uani 1 1 d . . . H39A H -0.1177 0.2019 0.0721 0.179 Uiso 1 1 calc R . . H39B H -0.0791 0.1588 0.1090 0.179 Uiso 1 1 calc R . . H39C H 0.0002 0.0707 0.0810 0.179 Uiso 1 1 calc R . . 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 O1 0.0600(18) 0.0562(18) 0.0487(16) -0.0048(14) -0.0019(14) 0.0051(14) C2 0.044(2) 0.058(3) 0.061(3) -0.008(2) 0.006(2) -0.007(2) C3 0.045(2) 0.055(3) 0.053(2) -0.006(2) 0.000(2) -0.0035(19) C4 0.050(3) 0.051(3) 0.059(3) -0.002(2) -0.005(2) -0.001(2) C5 0.048(3) 0.050(2) 0.044(2) -0.0008(19) 0.0029(19) 0.0006(19) C6 0.057(3) 0.049(3) 0.052(2) 0.008(2) 0.003(2) 0.005(2) C7 0.059(3) 0.057(3) 0.066(3) -0.006(2) 0.002(2) 0.011(2) C8 0.082(4) 0.050(3) 0.048(2) -0.001(2) 0.005(2) 0.012(2) C9 0.049(3) 0.052(3) 0.063(3) 0.006(2) 0.010(2) 0.006(2) C10 0.059(3) 0.052(3) 0.047(2) -0.006(2) 0.006(2) 0.006(2) C11 0.055(3) 0.053(3) 0.059(3) 0.003(2) 0.003(2) -0.003(2) C12 0.061(3) 0.048(3) 0.055(3) -0.007(2) 0.008(2) -0.002(2) C13 0.062(3) 0.052(3) 0.069(3) -0.007(2) 0.001(2) -0.003(2) C14 0.053(3) 0.048(3) 0.047(2) -0.003(2) -0.0046(19) -0.0043(19) C15 0.047(3) 0.060(3) 0.072(3) -0.006(3) 0.001(2) 0.005(2) C16 0.064(3) 0.057(3) 0.056(3) -0.007(2) -0.003(2) -0.002(2) C17 0.078(3) 0.054(3) 0.055(3) 0.003(2) -0.003(2) 0.001(2) B2 0.055(3) 0.038(3) 0.051(3) -0.009(2) -0.005(2) 0.019(2) C19 0.063(3) 0.091(4) 0.070(3) 0.002(3) 0.007(2) -0.001(3) C20 0.100(4) 0.059(3) 0.071(3) 0.008(3) 0.000(3) -0.008(3) C21 0.065(3) 0.056(3) 0.066(3) 0.000(2) -0.007(2) -0.005(2) B1 0.056(3) 0.051(3) 0.046(3) -0.004(2) 0.010(2) -0.007(2) C23 0.083(4) 0.049(3) 0.083(4) -0.006(2) 0.026(3) -0.001(3) C24 0.048(3) 0.061(3) 0.088(4) -0.014(3) -0.013(3) -0.001(2) C25 0.067(3) 0.068(4) 0.107(4) -0.011(3) 0.007(3) -0.007(3) C26 0.070(3) 0.087(4) 0.085(4) 0.012(3) -0.019(3) 0.008(3) C27 0.069(3) 0.074(4) 0.058(3) -0.004(3) 0.005(2) 0.006(3) C28 0.065(3) 0.077(4) 0.083(4) -0.004(3) -0.004(3) -0.003(3) C29 0.095(4) 0.058(3) 0.081(3) -0.018(3) 0.013(3) 0.005(3) C30 0.083(4) 0.084(4) 0.064(3) 0.014(3) 0.011(3) 0.008(3) C31 0.131(5) 0.051(3) 0.087(4) 0.001(3) 0.012(3) 0.020(3) C32 0.048(3) 0.086(4) 0.086(4) -0.021(3) 0.010(2) -0.004(2) C33 0.111(4) 0.050(3) 0.076(3) 0.008(3) -0.023(3) 0.010(3) C34 0.086(4) 0.084(4) 0.061(3) 0.012(3) 0.006(3) -0.015(3) C35 0.113(5) 0.067(3) 0.083(4) -0.012(3) 0.020(3) 0.017(3) C36 0.069(3) 0.085(4) 0.127(5) 0.016(4) -0.007(3) 0.018(3) C37 0.059(3) 0.084(4) 0.119(5) -0.029(4) 0.017(3) -0.016(3) C38 0.132(6) 0.135(6) 0.092(5) 0.016(4) 0.028(4) -0.011(5) C39 0.084(4) 0.112(5) 0.163(6) 0.005(5) 0.015(4) -0.035(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O1 B2 1.340(5) . ? O1 B1 1.348(6) . ? C2 C15 1.372(6) . ? C2 C3 1.424(6) . ? C2 C19 1.503(6) . ? C3 C11 1.412(6) . ? C3 B1 1.543(7) . ? C4 C13 1.388(6) . ? C4 C5 1.394(6) . ? C4 C37 1.500(6) . ? C5 C6 1.375(6) . ? C5 B1 1.596(6) . ? C6 C9 1.406(6) . ? C6 C32 1.503(6) . ? C7 C10 1.393(6) . ? C7 C28 1.410(7) . ? C7 C26 1.486(7) . ? C8 C9 1.367(6) . ? C8 C13 1.368(6) . ? C8 C35 1.506(6) . ? C10 C12 1.421(6) . ? C10 B2 1.582(7) . ? C11 C21 1.374(6) . ? C11 C30 1.497(6) . ? C12 C23 1.371(6) . ? C12 C33 1.507(6) . ? C14 C17 1.395(6) . ? C14 C16 1.416(6) . ? C14 B2 1.570(7) . ? C15 C24 1.368(7) . ? C16 C27 1.368(6) . ? C16 C29 1.499(7) . ? C17 C20 1.365(7) . ? C17 C31 1.530(7) . ? C20 C34 1.385(7) . ? C21 C24 1.393(7) . ? C23 C25 1.393(7) . ? C24 C36 1.488(7) . ? C25 C28 1.344(8) . ? C25 C39 1.514(8) . ? C27 C34 1.369(7) . ? C34 C38 1.499(7) . ? 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 B2 O1 B1 165.1(4) . . ? C15 C2 C3 119.8(4) . . ? C15 C2 C19 119.2(4) . . ? C3 C2 C19 120.9(4) . . ? C11 C3 C2 117.0(4) . . ? C11 C3 B1 121.4(4) . . ? C2 C3 B1 121.5(4) . . ? C13 C4 C5 119.3(4) . . ? C13 C4 C37 117.0(4) . . ? C5 C4 C37 123.7(4) . . ? C6 C5 C4 118.4(4) . . ? C6 C5 B1 121.2(4) . . ? C4 C5 B1 119.2(4) . . ? C5 C6 C9 120.3(4) . . ? C5 C6 C32 123.7(4) . . ? C9 C6 C32 116.0(4) . . ? C10 C7 C28 118.7(4) . . ? C10 C7 C26 122.5(4) . . ? C28 C7 C26 118.7(4) . . ? C9 C8 C13 117.1(4) . . ? C9 C8 C35 121.2(5) . . ? C13 C8 C35 121.7(5) . . ? C8 C9 C6 121.6(4) . . ? C7 C10 C12 118.6(4) . . ? C7 C10 B2 121.0(4) . . ? C12 C10 B2 120.4(4) . . ? C21 C11 C3 120.5(4) . . ? C21 C11 C30 119.6(4) . . ? C3 C11 C30 119.8(4) . . ? C23 C12 C10 119.8(4) . . ? C23 C12 C33 118.4(4) . . ? C10 C12 C33 121.8(4) . . ? C8 C13 C4 123.0(4) . . ? C17 C14 C16 116.8(4) . . ? C17 C14 B2 121.8(4) . . ? C16 C14 B2 121.0(4) . . ? C24 C15 C2 123.3(4) . . ? C27 C16 C14 119.9(4) . . ? C27 C16 C29 119.1(4) . . ? C14 C16 C29 121.0(4) . . ? C20 C17 C14 120.8(5) . . ? C20 C17 C31 118.0(4) . . ? C14 C17 C31 121.1(4) . . ? O1 B2 C14 116.2(4) . . ? O1 B2 C10 118.7(4) . . ? C14 B2 C10 125.1(4) . . ? C17 C20 C34 122.9(5) . . ? C11 C21 C24 122.1(5) . . ? O1 B1 C3 118.8(4) . . ? O1 B1 C5 118.3(4) . . ? C3 B1 C5 122.6(4) . . ? C12 C23 C25 121.8(5) . . ? C15 C24 C21 117.2(4) . . ? C15 C24 C36 122.8(5) . . ? C21 C24 C36 120.1(5) . . ? C28 C25 C23 118.2(5) . . ? C28 C25 C39 122.3(6) . . ? C23 C25 C39 119.5(6) . . ? C16 C27 C34 123.6(5) . . ? C25 C28 C7 122.9(5) . . ? C27 C34 C20 116.0(5) . . ? C27 C34 C38 123.1(6) . . ? C20 C34 C38 120.9(6) . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.300 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.059 data_cy511n1a _database_code_depnum_ccdc_archive 'CCDC 639174' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H28 B N' _chemical_formula_weight 365.30 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2148(10) _cell_length_b 11.6163(13) _cell_length_c 12.2308(14) _cell_angle_alpha 105.341(2) _cell_angle_beta 94.143(2) _cell_angle_gamma 106.575(2) _cell_volume 1064.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.139 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.820 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7481 _diffrn_reflns_av_R_equivalents 0.0164 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 28.22 _reflns_number_total 4761 _reflns_number_gt 2655 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0870P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4761 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0955 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1558 _refine_ls_wR_factor_gt 0.1406 _refine_ls_goodness_of_fit_ref 0.917 _refine_ls_restrained_S_all 0.917 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N N 0.35033(18) 0.16767(12) 0.19618(12) 0.0476(4) Uani 1 1 d . . . B B 0.2236(3) 0.09817(18) 0.25069(18) 0.0470(5) Uani 1 1 d . . . C1 C 0.4112(2) 0.11457(17) 0.09733(16) 0.0546(5) Uani 1 1 d . . . H1A H 0.3801 0.0286 0.0606 0.066 Uiso 1 1 calc R . . C2 C 0.5189(2) 0.20184(17) 0.06226(17) 0.0599(5) Uani 1 1 d . . . H2A H 0.5720 0.1878 -0.0024 0.072 Uiso 1 1 calc R . . C3 C 0.6392(3) 0.44401(19) 0.1549(2) 0.0732(6) Uani 1 1 d . . . H3A H 0.7090 0.4607 0.1007 0.088 Uiso 1 1 calc R . . C4 C 0.6356(3) 0.54011(19) 0.2478(2) 0.0776(7) Uani 1 1 d . . . H4A H 0.7026 0.6222 0.2559 0.093 Uiso 1 1 calc R . . C5 C 0.5325(3) 0.51542(17) 0.32970(19) 0.0683(6) Uani 1 1 d . . . H5A H 0.5334 0.5814 0.3927 0.082 Uiso 1 1 calc R . . C6 C 0.4297(2) 0.39567(16) 0.31929(17) 0.0559(5) Uani 1 1 d . . . H6A H 0.3599 0.3798 0.3737 0.067 Uiso 1 1 calc R . . C7 C 0.4331(2) 0.29882(15) 0.22481(15) 0.0473(4) Uani 1 1 d . . . C8 C 0.5379(2) 0.32206(16) 0.14279(16) 0.0535(5) Uani 1 1 d . . . C9 C 0.1101(2) 0.16647(14) 0.32310(15) 0.0440(4) Uani 1 1 d . . . C10 C 0.1041(2) 0.17261(15) 0.43916(16) 0.0497(4) Uani 1 1 d . . . C11 C 0.0023(2) 0.23496(16) 0.49996(16) 0.0574(5) Uani 1 1 d . . . H11A H 0.0012 0.2391 0.5769 0.069 Uiso 1 1 calc R . . C12 C -0.0976(2) 0.29101(17) 0.45018(18) 0.0574(5) Uani 1 1 d . . . C13 C -0.0928(2) 0.28368(15) 0.33627(17) 0.0544(5) Uani 1 1 d . . . H13A H -0.1593 0.3208 0.3014 0.065 Uiso 1 1 calc R . . C14 C 0.0070(2) 0.22332(15) 0.27133(15) 0.0482(4) Uani 1 1 d . . . C15 C -0.0007(3) 0.21891(18) 0.14686(16) 0.0616(5) Uani 1 1 d . . . H15A H -0.0901 0.2507 0.1256 0.092 Uiso 1 1 calc R . . H15B H -0.0246 0.1335 0.1001 0.092 Uiso 1 1 calc R . . H15C H 0.1077 0.2696 0.1355 0.092 Uiso 1 1 calc R . . C16 C -0.2070(3) 0.3586(2) 0.5185(2) 0.0863(7) Uani 1 1 d . . . H16A H -0.2915 0.3690 0.4668 0.129 Uiso 1 1 calc R . . H16B H -0.1352 0.4396 0.5667 0.129 Uiso 1 1 calc R . . H16C H -0.2637 0.3100 0.5652 0.129 Uiso 1 1 calc R . . C17 C 0.2127(3) 0.11698(18) 0.50132(17) 0.0659(6) Uani 1 1 d . . . H17A H 0.1818 0.1209 0.5761 0.099 Uiso 1 1 calc R . . H17B H 0.3321 0.1638 0.5090 0.099 Uiso 1 1 calc R . . H17C H 0.1933 0.0308 0.4583 0.099 Uiso 1 1 calc R . . C18 C 0.2067(2) -0.04608(15) 0.22794(15) 0.0466(4) Uani 1 1 d . . . C19 C 0.0492(2) -0.14152(15) 0.17966(15) 0.0482(4) Uani 1 1 d . . . C20 C 0.0411(3) -0.26725(16) 0.15479(16) 0.0559(5) Uani 1 1 d . . . H20A H -0.0633 -0.3293 0.1208 0.067 Uiso 1 1 calc R . . C21 C 0.1829(3) -0.30305(16) 0.17895(16) 0.0587(5) Uani 1 1 d . . . C22 C 0.3360(3) -0.20866(17) 0.23079(17) 0.0607(5) Uani 1 1 d . . . H22A H 0.4320 -0.2308 0.2501 0.073 Uiso 1 1 calc R . . C23 C 0.3511(2) -0.08169(15) 0.25506(16) 0.0545(5) Uani 1 1 d . . . C24 C 0.5241(3) 0.01326(18) 0.3131(2) 0.0769(7) Uani 1 1 d . . . H24A H 0.5075 0.0853 0.3653 0.115 Uiso 1 1 calc R . . H24B H 0.5877 0.0389 0.2561 0.115 Uiso 1 1 calc R . . H24C H 0.5869 -0.0241 0.3547 0.115 Uiso 1 1 calc R . . C25 C 0.1693(3) -0.44092(18) 0.1520(2) 0.0855(7) Uani 1 1 d . . . H25A H 0.0841 -0.4889 0.0852 0.128 Uiso 1 1 calc R . . H25B H 0.1367 -0.4702 0.2161 0.128 Uiso 1 1 calc R . . H25C H 0.2786 -0.4509 0.1376 0.128 Uiso 1 1 calc R . . C26 C -0.1147(2) -0.11399(18) 0.15119(19) 0.0664(6) Uani 1 1 d . . . H26A H -0.1022 -0.0718 0.0931 0.100 Uiso 1 1 calc R . . H26B H -0.1382 -0.0611 0.2189 0.100 Uiso 1 1 calc R . . H26C H -0.2082 -0.1915 0.1234 0.100 Uiso 1 1 calc R . . 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 N 0.0497(9) 0.0414(7) 0.0544(10) 0.0140(7) 0.0134(7) 0.0177(7) B 0.0442(12) 0.0482(11) 0.0499(13) 0.0178(9) 0.0018(9) 0.0150(9) C1 0.0566(12) 0.0524(10) 0.0570(12) 0.0101(9) 0.0152(10) 0.0247(9) C2 0.0579(12) 0.0655(12) 0.0610(13) 0.0198(10) 0.0201(10) 0.0233(10) C3 0.0691(15) 0.0674(13) 0.0862(17) 0.0346(13) 0.0293(12) 0.0116(11) C4 0.0765(16) 0.0518(12) 0.0978(19) 0.0237(12) 0.0222(14) 0.0068(11) C5 0.0715(15) 0.0477(11) 0.0786(15) 0.0126(10) 0.0136(12) 0.0136(10) C6 0.0579(12) 0.0480(10) 0.0607(13) 0.0135(9) 0.0118(10) 0.0171(9) C7 0.0455(10) 0.0447(9) 0.0548(12) 0.0184(8) 0.0077(9) 0.0160(8) C8 0.0486(11) 0.0552(11) 0.0601(12) 0.0219(9) 0.0127(9) 0.0163(9) C9 0.0437(10) 0.0395(8) 0.0494(11) 0.0150(8) 0.0075(8) 0.0125(8) C10 0.0496(11) 0.0445(9) 0.0532(12) 0.0170(8) 0.0053(9) 0.0106(8) C11 0.0641(13) 0.0602(11) 0.0462(12) 0.0141(9) 0.0131(10) 0.0177(10) C12 0.0547(12) 0.0544(10) 0.0608(14) 0.0096(9) 0.0134(10) 0.0195(9) C13 0.0506(12) 0.0515(10) 0.0644(14) 0.0181(9) 0.0073(9) 0.0207(9) C14 0.0483(11) 0.0440(9) 0.0532(12) 0.0155(8) 0.0079(8) 0.0150(8) C15 0.0689(13) 0.0688(12) 0.0596(13) 0.0282(10) 0.0094(10) 0.0328(11) C16 0.0938(18) 0.0955(16) 0.0775(17) 0.0127(13) 0.0279(14) 0.0507(15) C17 0.0759(15) 0.0711(12) 0.0574(13) 0.0250(10) 0.0066(11) 0.0290(11) C18 0.0470(11) 0.0441(9) 0.0514(11) 0.0167(8) 0.0101(8) 0.0158(8) C19 0.0490(11) 0.0477(10) 0.0488(11) 0.0164(8) 0.0108(8) 0.0141(9) C20 0.0612(13) 0.0470(10) 0.0534(12) 0.0149(9) 0.0062(9) 0.0086(9) C21 0.0812(15) 0.0443(10) 0.0521(12) 0.0162(9) 0.0115(11) 0.0204(10) C22 0.0699(14) 0.0570(11) 0.0657(13) 0.0233(10) 0.0094(11) 0.0319(11) C23 0.0526(12) 0.0492(10) 0.0648(13) 0.0200(9) 0.0080(9) 0.0183(9) C24 0.0551(13) 0.0627(12) 0.1119(19) 0.0275(12) -0.0028(12) 0.0199(11) C25 0.126(2) 0.0501(11) 0.0813(17) 0.0173(11) 0.0033(14) 0.0344(13) C26 0.0502(12) 0.0636(12) 0.0779(15) 0.0145(11) 0.0032(10) 0.0142(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N C1 1.400(2) . ? N C7 1.414(2) . ? N B 1.444(2) . ? B C9 1.566(3) . ? B C18 1.587(2) . ? C1 C2 1.329(2) . ? C2 C8 1.439(2) . ? C3 C4 1.375(3) . ? C3 C8 1.386(3) . ? C4 C5 1.393(3) . ? C5 C6 1.373(2) . ? C6 C7 1.392(2) . ? C7 C8 1.399(2) . ? C9 C10 1.408(2) . ? C9 C14 1.420(2) . ? C10 C11 1.388(2) . ? C10 C17 1.511(2) . ? C11 C12 1.382(2) . ? C12 C13 1.377(3) . ? C12 C16 1.512(3) . ? C13 C14 1.386(2) . ? C14 C15 1.506(2) . ? C18 C19 1.406(2) . ? C18 C23 1.409(2) . ? C19 C20 1.392(2) . ? C19 C26 1.508(2) . ? C20 C21 1.382(3) . ? C21 C22 1.384(3) . ? C21 C25 1.516(2) . ? C22 C23 1.392(2) . ? C23 C24 1.512(3) . ? 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 C1 N C7 105.52(14) . . ? C1 N B 125.04(14) . . ? C7 N B 129.39(15) . . ? N B C9 119.17(14) . . ? N B C18 115.99(15) . . ? C9 B C18 124.81(15) . . ? C2 C1 N 111.87(16) . . ? C1 C2 C8 107.34(17) . . ? C4 C3 C8 119.37(19) . . ? C3 C4 C5 120.52(19) . . ? C6 C5 C4 121.3(2) . . ? C5 C6 C7 117.92(18) . . ? C6 C7 C8 121.32(16) . . ? C6 C7 N 130.12(16) . . ? C8 C7 N 108.44(15) . . ? C3 C8 C7 119.53(18) . . ? C3 C8 C2 133.58(18) . . ? C7 C8 C2 106.79(16) . . ? C10 C9 C14 117.90(15) . . ? C10 C9 B 122.16(15) . . ? C14 C9 B 119.94(15) . . ? C11 C10 C9 120.01(16) . . ? C11 C10 C17 118.72(16) . . ? C9 C10 C17 121.22(16) . . ? C12 C11 C10 122.32(17) . . ? C13 C12 C11 117.49(17) . . ? C13 C12 C16 121.28(19) . . ? C11 C12 C16 121.22(19) . . ? C12 C13 C14 122.82(17) . . ? C13 C14 C9 119.44(16) . . ? C13 C14 C15 118.20(15) . . ? C9 C14 C15 122.35(15) . . ? C19 C18 C23 118.18(14) . . ? C19 C18 B 121.45(15) . . ? C23 C18 B 120.37(16) . . ? C20 C19 C18 119.95(17) . . ? C20 C19 C26 117.42(16) . . ? C18 C19 C26 122.63(15) . . ? C21 C20 C19 122.21(18) . . ? C20 C21 C22 117.56(16) . . ? C20 C21 C25 120.92(19) . . ? C22 C21 C25 121.50(19) . . ? C21 C22 C23 122.23(18) . . ? C22 C23 C18 119.79(17) . . ? C22 C23 C24 117.65(17) . . ? C18 C23 C24 122.54(15) . . ? _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 28.22 _diffrn_measured_fraction_theta_full 0.907 _refine_diff_density_max 0.279 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.035 # Attachment 'Comp2.CIF' data_cy611a _database_code_depnum_ccdc_archive 'CCDC 639175' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H30 B N' _chemical_formula_weight 379.33 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 22.3981(18) _cell_length_b 8.1607(7) _cell_length_c 12.2170(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2233.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.128 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.810 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14894 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 28.25 _reflns_number_total 5067 _reflns_number_gt 3234 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 'Cannot be reliably determined' _refine_ls_number_reflns 5067 _refine_ls_number_parameters 281 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0795 _refine_ls_goodness_of_fit_ref 0.900 _refine_ls_restrained_S_all 0.900 _refine_ls_shift/su_max 0.050 _refine_ls_shift/su_mean 0.002 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B B 0.82950(8) 0.8388(2) 0.25605(17) 0.0458(4) Uani 1 1 d . . . N N 0.86532(6) 0.93744(15) 0.18209(12) 0.0483(3) Uani 1 1 d . . . C1 C 0.84593(8) 1.0205(2) 0.08610(16) 0.0559(5) Uani 1 1 d . . . C2 C 0.89142(10) 1.1053(2) 0.04335(17) 0.0634(5) Uani 1 1 d . . . C3 C 1.00089(10) 1.1488(2) 0.1075(2) 0.0731(6) Uani 1 1 d . . . H3A H 1.0128 1.2173 0.0507 0.088 Uiso 1 1 calc R . . C4 C 1.03967(9) 1.1088(3) 0.1900(3) 0.0803(6) Uani 1 1 d . . . H4A H 1.0784 1.1498 0.1885 0.096 Uiso 1 1 calc R . . C5 C 1.02225(8) 1.0086(2) 0.27555(19) 0.0701(6) Uani 1 1 d . . . H5A H 1.0492 0.9854 0.3313 0.084 Uiso 1 1 calc R . . C6 C 0.96533(8) 0.9421(2) 0.2796(2) 0.0596(5) Uani 1 1 d . . . C7 C 0.92644(8) 0.97884(18) 0.19562(15) 0.0495(4) Uani 1 1 d . . . C8 C 0.94326(8) 1.0846(2) 0.11047(16) 0.0572(5) Uani 1 1 d . . . C9 C 0.86042(6) 0.69545(17) 0.32118(14) 0.0437(4) Uani 1 1 d . . . C10 C 0.85590(7) 0.68446(18) 0.43700(14) 0.0464(4) Uani 1 1 d . . . C11 C 0.88143(7) 0.55258(19) 0.49153(16) 0.0523(4) Uani 1 1 d . . . H11A H 0.8783 0.5473 0.5674 0.063 Uiso 1 1 calc R . . C12 C 0.91153(7) 0.42831(19) 0.43674(16) 0.0525(4) Uani 1 1 d . . . C13 C 0.91518(7) 0.43930(19) 0.32436(17) 0.0526(4) Uani 1 1 d . . . H13A H 0.9344 0.3560 0.2862 0.063 Uiso 1 1 calc R . . C14 C 0.89124(7) 0.56985(18) 0.26550(15) 0.0503(4) Uani 1 1 d . . . C15 C 0.89818(10) 0.5674(2) 0.14252(16) 0.0742(6) Uani 1 1 d . . . H15A H 0.9164 0.4662 0.1205 0.111 Uiso 1 1 calc R . . H15B H 0.9229 0.6574 0.1201 0.111 Uiso 1 1 calc R . . H15C H 0.8596 0.5772 0.1088 0.111 Uiso 1 1 calc R . . C16 C 0.93795(10) 0.2853(2) 0.49814(19) 0.0773(6) Uani 1 1 d . . . H16A H 0.9645 0.2259 0.4508 0.116 Uiso 1 1 calc R . . H16B H 0.9065 0.2140 0.5222 0.116 Uiso 1 1 calc R . . H16C H 0.9597 0.3249 0.5605 0.116 Uiso 1 1 calc R . . C17 C 0.82674(9) 0.8160(2) 0.50415(16) 0.0610(5) Uani 1 1 d . . . H17A H 0.8248 0.7817 0.5792 0.091 Uiso 1 1 calc R . . H17B H 0.7871 0.8355 0.4772 0.091 Uiso 1 1 calc R . . H17C H 0.8497 0.9151 0.4989 0.091 Uiso 1 1 calc R . . C18 C 0.76131(7) 0.87967(18) 0.26955(15) 0.0473(4) Uani 1 1 d . . . C19 C 0.71655(7) 0.7614(2) 0.25189(14) 0.0517(4) Uani 1 1 d . . . C20 C 0.65708(8) 0.8000(3) 0.27043(17) 0.0611(5) Uani 1 1 d . . . C21 C 0.63948(7) 0.9514(2) 0.30944(16) 0.0625(5) Uani 1 1 d . . . C22 C 0.68321(8) 1.0664(2) 0.32713(17) 0.0620(5) Uani 1 1 d . . . H22A H 0.6723 1.1688 0.3540 0.074 Uiso 1 1 calc R . . C23 C 0.74340(7) 1.0351(2) 0.30625(15) 0.0535(4) Uani 1 1 d . . . C24 C 0.78795(9) 1.1718(2) 0.3266(2) 0.0744(6) Uani 1 1 d . . . H24A H 0.7686 1.2598 0.3649 0.112 Uiso 1 1 calc R . . H24B H 0.8030 1.2112 0.2579 0.112 Uiso 1 1 calc R . . H24C H 0.8204 1.1309 0.3700 0.112 Uiso 1 1 calc R . . C25 C 0.57411(9) 0.9880(3) 0.3303(2) 0.0901(7) Uani 1 1 d . . . H25A H 0.5707 1.0863 0.3731 0.135 Uiso 1 1 calc R . . H25B H 0.5563 0.8983 0.3694 0.135 Uiso 1 1 calc R . . H25C H 0.5539 1.0027 0.2617 0.135 Uiso 1 1 calc R . . C26 C 0.73182(9) 0.5938(2) 0.2063(2) 0.0766(6) Uani 1 1 d . . . H26A H 0.6983 0.5219 0.2152 0.115 Uiso 1 1 calc R . . H26B H 0.7656 0.5500 0.2449 0.115 Uiso 1 1 calc R . . H26C H 0.7413 0.6034 0.1299 0.115 Uiso 1 1 calc R . . C27 C 0.78547(10) 0.9975(3) 0.03826(19) 0.0799(6) Uani 1 1 d . . . H27A H 0.7844 1.0442 -0.0338 0.120 Uiso 1 1 calc R . . H27B H 0.7564 1.0508 0.0837 0.120 Uiso 1 1 calc R . . H27C H 0.7766 0.8826 0.0340 0.120 Uiso 1 1 calc R . . H20 H 0.6275(7) 0.7254(19) 0.2580(15) 0.055(5) Uiso 1 1 d . . . H6 H 0.9576(8) 0.879(2) 0.3343(16) 0.060(6) Uiso 1 1 d . . . H2 H 0.8877(8) 1.163(2) -0.0218(17) 0.068(6) Uiso 1 1 d . . . 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 B 0.0535(11) 0.0414(10) 0.0426(11) -0.0100(9) -0.0014(10) -0.0054(8) N 0.0486(8) 0.0490(7) 0.0473(9) 0.0033(7) 0.0004(7) 0.0020(6) C1 0.0663(12) 0.0528(10) 0.0484(11) 0.0032(9) 0.0002(10) 0.0066(9) C2 0.0859(15) 0.0572(11) 0.0470(12) 0.0117(10) 0.0098(11) 0.0057(10) C3 0.0688(14) 0.0698(12) 0.0807(16) 0.0002(12) 0.0278(13) -0.0070(11) C4 0.0518(12) 0.0786(14) 0.1104(19) -0.0173(14) 0.0223(14) -0.0100(10) C5 0.0499(11) 0.0715(12) 0.0887(17) -0.0058(13) -0.0019(11) 0.0013(9) C6 0.0525(11) 0.0569(11) 0.0694(15) 0.0064(12) 0.0018(10) 0.0004(9) C7 0.0510(10) 0.0451(9) 0.0525(11) -0.0021(9) 0.0076(9) 0.0049(7) C8 0.0617(12) 0.0517(10) 0.0581(12) -0.0015(9) 0.0169(10) 0.0008(8) C9 0.0429(9) 0.0441(8) 0.0443(10) -0.0027(8) 0.0015(8) -0.0043(7) C10 0.0466(10) 0.0456(9) 0.0470(11) -0.0027(8) 0.0038(8) -0.0048(7) C11 0.0553(11) 0.0556(11) 0.0462(11) 0.0031(9) -0.0022(9) -0.0050(8) C12 0.0511(10) 0.0476(10) 0.0587(13) 0.0050(9) -0.0018(9) -0.0043(7) C13 0.0512(10) 0.0447(9) 0.0618(13) -0.0036(9) 0.0094(9) 0.0036(7) C14 0.0504(10) 0.0498(10) 0.0507(11) -0.0012(9) 0.0085(9) -0.0009(8) C15 0.1000(16) 0.0683(13) 0.0544(14) -0.0062(10) 0.0152(11) 0.0141(11) C16 0.0853(14) 0.0641(11) 0.0827(15) 0.0105(12) -0.0042(12) 0.0176(10) C17 0.0764(12) 0.0572(11) 0.0494(12) -0.0067(9) 0.0038(10) 0.0051(9) C18 0.0505(9) 0.0469(9) 0.0445(10) 0.0011(8) -0.0012(8) -0.0028(7) C19 0.0536(10) 0.0552(10) 0.0463(10) 0.0064(8) -0.0024(9) -0.0070(8) C20 0.0511(11) 0.0735(13) 0.0588(12) 0.0150(11) -0.0048(10) -0.0174(10) C21 0.0481(10) 0.0803(13) 0.0590(13) 0.0198(11) 0.0004(10) 0.0039(10) C22 0.0606(12) 0.0625(11) 0.0627(12) 0.0037(10) 0.0059(10) 0.0133(9) C23 0.0507(10) 0.0515(9) 0.0583(12) 0.0030(8) 0.0011(9) 0.0007(7) C24 0.0732(12) 0.0482(10) 0.1017(17) -0.0137(11) 0.0040(12) 0.0009(8) C25 0.0522(11) 0.1188(17) 0.0993(18) 0.0290(16) 0.0051(12) 0.0154(11) C26 0.0807(14) 0.0622(11) 0.0868(16) -0.0168(11) -0.0065(13) -0.0176(10) C27 0.0795(15) 0.0989(15) 0.0613(14) 0.0120(12) -0.0144(12) 0.0053(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 B N 1.452(2) . ? B C18 1.572(3) . ? B C9 1.575(3) . ? N C7 1.420(2) . ? N C1 1.423(2) . ? C1 C2 1.338(3) . ? C1 C27 1.487(3) . ? C2 C8 1.431(3) . ? C3 C4 1.370(3) . ? C3 C8 1.393(3) . ? C4 C5 1.383(3) . ? C5 C6 1.386(2) . ? C6 C7 1.379(3) . ? C7 C8 1.403(2) . ? C9 C14 1.411(2) . ? C9 C10 1.421(2) . ? C10 C11 1.389(2) . ? C10 C17 1.501(2) . ? C11 C12 1.390(2) . ? C12 C13 1.378(3) . ? C12 C16 1.508(2) . ? C13 C14 1.393(2) . ? C14 C15 1.511(3) . ? C18 C23 1.404(2) . ? C18 C19 1.408(2) . ? C19 C20 1.387(2) . ? C19 C26 1.516(3) . ? C20 C21 1.382(3) . ? C21 C22 1.374(2) . ? C21 C25 1.516(3) . ? C22 C23 1.396(2) . ? C23 C24 1.517(2) . ? 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 N B C18 118.98(15) . . ? N B C9 118.90(14) . . ? C18 B C9 122.12(15) . . ? C7 N C1 106.08(14) . . ? C7 N B 126.32(14) . . ? C1 N B 127.49(14) . . ? C2 C1 N 109.63(17) . . ? C2 C1 C27 127.27(19) . . ? N C1 C27 122.80(16) . . ? C1 C2 C8 109.45(18) . . ? C4 C3 C8 118.6(2) . . ? C3 C4 C5 121.19(18) . . ? C4 C5 C6 121.2(2) . . ? C7 C6 C5 118.0(2) . . ? C6 C7 C8 121.04(17) . . ? C6 C7 N 130.11(17) . . ? C8 C7 N 108.60(16) . . ? C3 C8 C7 119.94(19) . . ? C3 C8 C2 133.80(19) . . ? C7 C8 C2 106.23(16) . . ? C14 C9 C10 117.97(15) . . ? C14 C9 B 120.74(16) . . ? C10 C9 B 121.23(14) . . ? C11 C10 C9 119.81(15) . . ? C11 C10 C17 118.12(16) . . ? C9 C10 C17 122.00(15) . . ? C10 C11 C12 122.28(17) . . ? C13 C12 C11 117.46(16) . . ? C13 C12 C16 121.50(17) . . ? C11 C12 C16 121.03(18) . . ? C12 C13 C14 122.77(16) . . ? C13 C14 C9 119.69(16) . . ? C13 C14 C15 117.64(16) . . ? C9 C14 C15 122.65(16) . . ? C23 C18 C19 117.70(14) . . ? C23 C18 B 120.18(13) . . ? C19 C18 B 122.02(14) . . ? C20 C19 C18 120.21(16) . . ? C20 C19 C26 118.77(16) . . ? C18 C19 C26 120.93(15) . . ? C21 C20 C19 122.21(17) . . ? C22 C21 C20 117.52(16) . . ? C22 C21 C25 121.82(19) . . ? C20 C21 C25 120.66(18) . . ? C21 C22 C23 122.34(17) . . ? C22 C23 C18 119.97(15) . . ? C22 C23 C24 118.09(15) . . ? C18 C23 C24 121.92(14) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.119 _refine_diff_density_min -0.116 _refine_diff_density_rms 0.024 # Attachment 'Comp3..CIF' data_cy521t _database_code_depnum_ccdc_archive 'CCDC 639176' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 3 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H30 B N' _chemical_formula_weight 379.33 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.635(4) _cell_length_b 11.606(6) _cell_length_c 12.262(7) _cell_angle_alpha 99.281(9) _cell_angle_beta 98.716(9) _cell_angle_gamma 107.487(9) _cell_volume 1130.3(10) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.115 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.628 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6724 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3961 _reflns_number_gt 2471 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1090P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment Mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3961 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1761 _refine_ls_wR_factor_gt 0.1590 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B B 0.2845(3) 0.8751(2) 0.23116(19) 0.0554(6) Uani 1 1 d . . . N N 0.1574(2) 0.80103(16) 0.27892(14) 0.0622(5) Uani 1 1 d . . . C1 C 0.1014(3) 0.8503(3) 0.37602(19) 0.0679(6) Uani 1 1 d . . . H1 H 0.139(3) 0.939(2) 0.4090(19) 0.082(7) Uiso 1 1 d . . . C2 C 0.0043(3) 0.7588(3) 0.4137(2) 0.0759(7) Uani 1 1 d . . . C3 C -0.1065(3) 0.5207(3) 0.3331(3) 0.0934(8) Uani 1 1 d . . . H3 H -0.172(4) 0.510(3) 0.398(3) 0.141(12) Uiso 1 1 d . . . C4 C -0.1023(4) 0.4313(3) 0.2463(3) 0.0971(9) Uani 1 1 d . . . H4 H -0.174(4) 0.344(3) 0.243(2) 0.117(9) Uiso 1 1 d . . . C5 C -0.0119(3) 0.4614(2) 0.1674(2) 0.0909(8) Uani 1 1 d . . . H5A H -0.0131 0.3989 0.1090 0.109 Uiso 1 1 calc R . . C6 C 0.0830(3) 0.5837(2) 0.1716(2) 0.0724(6) Uani 1 1 d . . . H6 H 0.142(3) 0.605(2) 0.1120(19) 0.072(6) Uiso 1 1 d . . . C7 C 0.0809(2) 0.6724(2) 0.25734(19) 0.0649(6) Uani 1 1 d . . . C8 C -0.0147(2) 0.6454(2) 0.33889(19) 0.0639(6) Uani 1 1 d . . . C9 C 0.3941(2) 0.81182(18) 0.16889(17) 0.0544(5) Uani 1 1 d . . . C10 C 0.4044(2) 0.81497(18) 0.05689(17) 0.0569(5) Uani 1 1 d . . . C11 C 0.5045(3) 0.7598(2) 0.0055(2) 0.0659(6) Uani 1 1 d . . . H11 H 0.508(2) 0.7602(19) -0.073(2) 0.071(6) Uiso 1 1 d . . . C12 C 0.5994(3) 0.7023(2) 0.0632(2) 0.0678(6) Uani 1 1 d . . . C13 C 0.5898(3) 0.7007(2) 0.1740(2) 0.0678(6) Uani 1 1 d . . . H13 H 0.651(3) 0.6655(19) 0.2161(17) 0.063(6) Uiso 1 1 d . . . C14 C 0.4892(2) 0.75369(19) 0.22814(18) 0.0626(6) Uani 1 1 d . . . C15 C 0.4897(3) 0.7464(2) 0.34987(19) 0.0818(7) Uani 1 1 d . . . H15A H 0.5742 0.7137 0.3771 0.123 Uiso 1 1 calc R . . H15B H 0.3832 0.6932 0.3553 0.123 Uiso 1 1 calc R . . H15C H 0.5120 0.8277 0.3947 0.123 Uiso 1 1 calc R . . C16 C 0.7066(3) 0.6415(3) 0.0069(2) 0.0942(8) Uani 1 1 d . . . H16A H 0.7674 0.6951 -0.0353 0.141 Uiso 1 1 calc R . . H16B H 0.6378 0.5646 -0.0433 0.141 Uiso 1 1 calc R . . H16C H 0.7831 0.6260 0.0634 0.141 Uiso 1 1 calc R . . C17 C 0.3038(3) 0.8747(2) -0.01197(18) 0.0707(6) Uani 1 1 d . . . H17A H 0.3297 0.9596 0.0255 0.106 Uiso 1 1 calc R . . H17B H 0.1876 0.8314 -0.0197 0.106 Uiso 1 1 calc R . . H17C H 0.3301 0.8712 -0.0855 0.106 Uiso 1 1 calc R . . C18 C 0.3103(2) 1.01769(18) 0.25152(16) 0.0555(5) Uani 1 1 d . . . C19 C 0.4652(2) 1.1066(2) 0.30544(17) 0.0615(6) Uani 1 1 d . . . C20 C 0.4813(3) 1.2314(2) 0.32682(19) 0.0700(6) Uani 1 1 d . . . H20 H 0.590(3) 1.288(2) 0.3664(19) 0.078(7) Uiso 1 1 d . . . C21 C 0.3535(3) 1.2734(2) 0.2944(2) 0.0711(6) Uani 1 1 d . . . C22 C 0.2033(3) 1.1865(2) 0.23836(19) 0.0675(6) Uani 1 1 d . . . H22 H 0.113(3) 1.217(2) 0.2172(19) 0.080(7) Uiso 1 1 d . . . C23 C 0.1781(2) 1.06066(19) 0.21781(17) 0.0583(5) Uani 1 1 d . . . C24 C 0.0071(3) 0.9737(2) 0.1585(2) 0.0769(7) Uani 1 1 d . . . H24A H -0.0530 1.0180 0.1200 0.115 Uiso 1 1 calc R . . H24B H -0.0512 0.9401 0.2131 0.115 Uiso 1 1 calc R . . H24C H 0.0165 0.9075 0.1047 0.115 Uiso 1 1 calc R . . C25 C 0.3768(4) 1.4102(2) 0.3204(3) 0.1023(9) Uani 1 1 d . . . H25A H 0.2717 1.4212 0.3237 0.153 Uiso 1 1 calc R . . H25B H 0.4209 1.4470 0.2621 0.153 Uiso 1 1 calc R . . H25C H 0.4526 1.4492 0.3918 0.153 Uiso 1 1 calc R . . C26 C 0.6159(3) 1.0719(2) 0.3438(2) 0.0901(8) Uani 1 1 d . . . H26A H 0.7108 1.1456 0.3726 0.135 Uiso 1 1 calc R . . H26B H 0.6358 1.0213 0.2810 0.135 Uiso 1 1 calc R . . H26C H 0.5972 1.0266 0.4023 0.135 Uiso 1 1 calc R . . C27 C -0.0715(3) 0.7720(3) 0.5149(2) 0.0958(9) Uani 1 1 d . . . H27A H -0.0404 0.8581 0.5501 0.144 Uiso 1 1 calc R . . H27B H -0.0325 0.7290 0.5678 0.144 Uiso 1 1 calc R . . H27C H -0.1903 0.7373 0.4918 0.144 Uiso 1 1 calc R . . 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 B 0.0527(12) 0.0576(15) 0.0510(13) 0.0137(11) 0.0016(10) 0.0149(11) N 0.0658(10) 0.0571(11) 0.0633(11) 0.0172(9) 0.0115(9) 0.0189(9) C1 0.0634(13) 0.0793(18) 0.0629(14) 0.0221(13) 0.0148(11) 0.0226(13) C2 0.0638(13) 0.0952(19) 0.0690(15) 0.0207(14) 0.0142(12) 0.0255(13) C3 0.0813(17) 0.087(2) 0.107(2) 0.0341(18) 0.0270(17) 0.0102(15) C4 0.0956(19) 0.0625(18) 0.117(2) 0.0165(18) 0.0259(18) 0.0025(16) C5 0.0969(18) 0.0626(17) 0.103(2) 0.0114(15) 0.0177(16) 0.0172(15) C6 0.0737(14) 0.0687(17) 0.0739(16) 0.0153(13) 0.0153(13) 0.0230(13) C7 0.0611(12) 0.0594(14) 0.0708(14) 0.0172(12) 0.0060(11) 0.0176(11) C8 0.0523(11) 0.0695(16) 0.0664(14) 0.0195(12) 0.0115(10) 0.0135(11) C9 0.0543(11) 0.0455(11) 0.0576(12) 0.0113(9) 0.0048(9) 0.0116(9) C10 0.0562(11) 0.0472(12) 0.0607(13) 0.0100(10) 0.0078(10) 0.0110(10) C11 0.0706(13) 0.0592(14) 0.0616(14) 0.0071(11) 0.0165(11) 0.0146(11) C12 0.0609(12) 0.0577(14) 0.0796(16) 0.0062(12) 0.0125(11) 0.0179(11) C13 0.0629(13) 0.0574(14) 0.0804(17) 0.0158(12) 0.0026(12) 0.0223(11) C14 0.0633(12) 0.0546(13) 0.0665(14) 0.0128(10) 0.0066(10) 0.0184(11) C15 0.0969(17) 0.0871(18) 0.0698(15) 0.0281(13) 0.0067(13) 0.0422(15) C16 0.0853(16) 0.092(2) 0.107(2) 0.0033(16) 0.0247(15) 0.0392(15) C17 0.0818(14) 0.0679(15) 0.0622(13) 0.0183(11) 0.0089(11) 0.0258(12) C18 0.0595(11) 0.0536(12) 0.0520(12) 0.0132(9) 0.0131(9) 0.0155(10) C19 0.0603(12) 0.0560(14) 0.0604(13) 0.0111(10) 0.0101(10) 0.0102(10) C20 0.0722(15) 0.0573(15) 0.0669(15) 0.0087(11) 0.0143(12) 0.0050(13) C21 0.0915(16) 0.0535(14) 0.0698(14) 0.0136(11) 0.0308(13) 0.0197(13) C22 0.0795(15) 0.0624(16) 0.0712(15) 0.0216(12) 0.0240(12) 0.0314(13) C23 0.0629(12) 0.0554(13) 0.0584(12) 0.0147(10) 0.0153(10) 0.0202(10) C24 0.0638(13) 0.0757(16) 0.0897(17) 0.0210(13) 0.0054(12) 0.0246(12) C25 0.135(2) 0.0570(16) 0.112(2) 0.0137(15) 0.0321(19) 0.0277(16) C26 0.0651(14) 0.0816(18) 0.102(2) 0.0087(15) -0.0072(13) 0.0122(13) C27 0.0802(16) 0.138(3) 0.0791(17) 0.0229(16) 0.0339(14) 0.0421(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 B N 1.442(3) . ? B C9 1.573(3) . ? B C18 1.574(3) . ? N C7 1.401(3) . ? N C1 1.449(3) . ? C1 C2 1.336(3) . ? C2 C8 1.426(3) . ? C2 C27 1.496(3) . ? C3 C4 1.374(4) . ? C3 C8 1.410(3) . ? C4 C5 1.357(4) . ? C5 C6 1.398(4) . ? C6 C7 1.354(3) . ? C7 C8 1.405(3) . ? C9 C10 1.395(3) . ? C9 C14 1.403(3) . ? C10 C11 1.386(3) . ? C10 C17 1.509(3) . ? C11 C12 1.387(3) . ? C12 C13 1.375(3) . ? C12 C16 1.503(3) . ? C13 C14 1.392(3) . ? C14 C15 1.508(3) . ? C18 C19 1.405(3) . ? C18 C23 1.410(3) . ? C19 C20 1.390(3) . ? C19 C26 1.506(3) . ? C20 C21 1.366(3) . ? C21 C22 1.376(3) . ? C21 C25 1.512(3) . ? C22 C23 1.384(3) . ? C23 C24 1.507(3) . ? 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 N B C9 119.00(19) . . ? N B C18 116.66(18) . . ? C9 B C18 124.25(18) . . ? C7 N B 130.45(18) . . ? C7 N C1 105.49(18) . . ? B N C1 123.47(19) . . ? C2 C1 N 110.7(2) . . ? C1 C2 C8 107.2(2) . . ? C1 C2 C27 126.7(3) . . ? C8 C2 C27 126.1(2) . . ? C4 C3 C8 118.6(3) . . ? C5 C4 C3 121.2(3) . . ? C4 C5 C6 121.8(3) . . ? C7 C6 C5 117.5(3) . . ? C6 C7 N 129.4(2) . . ? C6 C7 C8 122.4(2) . . ? N C7 C8 108.04(19) . . ? C7 C8 C3 118.4(2) . . ? C7 C8 C2 108.5(2) . . ? C3 C8 C2 133.1(2) . . ? C10 C9 C14 118.46(19) . . ? C10 C9 B 122.04(17) . . ? C14 C9 B 119.47(18) . . ? C11 C10 C9 120.3(2) . . ? C11 C10 C17 118.51(19) . . ? C9 C10 C17 121.12(18) . . ? C10 C11 C12 121.7(2) . . ? C13 C12 C11 117.6(2) . . ? C13 C12 C16 120.8(2) . . ? C11 C12 C16 121.6(2) . . ? C12 C13 C14 122.4(2) . . ? C13 C14 C9 119.5(2) . . ? C13 C14 C15 117.5(2) . . ? C9 C14 C15 123.01(19) . . ? C19 C18 C23 117.62(19) . . ? C19 C18 B 121.20(18) . . ? C23 C18 B 121.18(17) . . ? C20 C19 C18 119.6(2) . . ? C20 C19 C26 118.0(2) . . ? C18 C19 C26 122.4(2) . . ? C21 C20 C19 122.9(2) . . ? C20 C21 C22 117.4(2) . . ? C20 C21 C25 121.0(2) . . ? C22 C21 C25 121.6(2) . . ? C21 C22 C23 122.3(2) . . ? C22 C23 C18 120.1(2) . . ? C22 C23 C24 117.78(19) . . ? C18 C23 C24 122.16(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 B N C7 -18.3(3) . . . . ? C18 B N C7 165.01(19) . . . . ? C9 B N C1 151.52(18) . . . . ? C18 B N C1 -25.1(3) . . . . ? C7 N C1 C2 2.4(2) . . . . ? B N C1 C2 -169.55(18) . . . . ? N C1 C2 C8 -3.0(2) . . . . ? N C1 C2 C27 177.2(2) . . . . ? C8 C3 C4 C5 0.1(4) . . . . ? C3 C4 C5 C6 1.0(4) . . . . ? C4 C5 C6 C7 -0.5(4) . . . . ? C5 C6 C7 N -176.9(2) . . . . ? C5 C6 C7 C8 -1.3(3) . . . . ? B N C7 C6 -13.6(4) . . . . ? C1 N C7 C6 175.2(2) . . . . ? B N C7 C8 170.37(18) . . . . ? C1 N C7 C8 -0.8(2) . . . . ? C6 C7 C8 C3 2.5(3) . . . . ? N C7 C8 C3 178.89(19) . . . . ? C6 C7 C8 C2 -177.3(2) . . . . ? N C7 C8 C2 -0.9(2) . . . . ? C4 C3 C8 C7 -1.8(4) . . . . ? C4 C3 C8 C2 177.9(3) . . . . ? C1 C2 C8 C7 2.4(2) . . . . ? C27 C2 C8 C7 -177.8(2) . . . . ? C1 C2 C8 C3 -177.3(2) . . . . ? C27 C2 C8 C3 2.5(4) . . . . ? N B C9 C10 123.0(2) . . . . ? C18 B C9 C10 -60.6(3) . . . . ? N B C9 C14 -59.2(2) . . . . ? C18 B C9 C14 117.2(2) . . . . ? C14 C9 C10 C11 1.1(3) . . . . ? B C9 C10 C11 178.92(18) . . . . ? C14 C9 C10 C17 179.28(17) . . . . ? B C9 C10 C17 -2.9(3) . . . . ? C9 C10 C11 C12 -1.2(3) . . . . ? C17 C10 C11 C12 -179.48(19) . . . . ? C10 C11 C12 C13 0.5(3) . . . . ? C10 C11 C12 C16 179.4(2) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C16 C12 C13 C14 -178.6(2) . . . . ? C12 C13 C14 C9 -0.4(3) . . . . ? C12 C13 C14 C15 -179.8(2) . . . . ? C10 C9 C14 C13 -0.3(3) . . . . ? B C9 C14 C13 -178.19(19) . . . . ? C10 C9 C14 C15 179.1(2) . . . . ? B C9 C14 C15 1.2(3) . . . . ? N B C18 C19 122.3(2) . . . . ? C9 B C18 C19 -54.2(3) . . . . ? N B C18 C23 -56.7(3) . . . . ? C9 B C18 C23 126.8(2) . . . . ? C23 C18 C19 C20 2.1(3) . . . . ? B C18 C19 C20 -176.93(19) . . . . ? C23 C18 C19 C26 -179.19(19) . . . . ? B C18 C19 C26 1.8(3) . . . . ? C18 C19 C20 C21 -2.2(3) . . . . ? C26 C19 C20 C21 179.1(2) . . . . ? C19 C20 C21 C22 0.1(3) . . . . ? C19 C20 C21 C25 179.5(2) . . . . ? C20 C21 C22 C23 2.0(3) . . . . ? C25 C21 C22 C23 -177.4(2) . . . . ? C21 C22 C23 C18 -2.0(3) . . . . ? C21 C22 C23 C24 178.3(2) . . . . ? C19 C18 C23 C22 -0.1(3) . . . . ? B C18 C23 C22 178.93(19) . . . . ? C19 C18 C23 C24 179.52(19) . . . . ? B C18 C23 C24 -1.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.305 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.036 # Attachment 'comp4.CIF' data_cy612a _database_code_depnum_ccdc_archive 'CCDC 639177' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H30 B N' _chemical_formula_weight 379.33 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4989(11) _cell_length_b 10.0999(14) _cell_length_c 14.424(2) _cell_angle_alpha 100.384(2) _cell_angle_beta 106.956(2) _cell_angle_gamma 103.731(2) _cell_volume 1108.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.137 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.820 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7919 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0872 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 28.28 _reflns_number_total 5020 _reflns_number_gt 2068 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0640P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5020 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1386 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1419 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 0.832 _refine_ls_restrained_S_all 0.832 _refine_ls_shift/su_max 0.031 _refine_ls_shift/su_mean 0.001 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N N 0.0681(2) 0.95740(17) 0.22343(12) 0.0519(5) Uani 1 1 d . . . B B -0.0579(3) 0.8222(3) 0.20831(17) 0.0479(6) Uani 1 1 d . . . C1 C 0.0649(3) 1.0120(2) 0.13888(17) 0.0638(6) Uani 1 1 d . . . H1A H -0.0267 0.9797 0.0778 0.077 Uiso 1 1 calc R . . C2 C 0.2093(3) 1.1148(2) 0.15858(19) 0.0713(7) Uani 1 1 d . . . H2A H 0.2373 1.1631 0.1136 0.086 Uiso 1 1 calc R . . C3 C 0.4716(3) 1.2389(3) 0.3213(2) 0.0769(7) Uani 1 1 d . . . H3A H 0.5328 1.3013 0.2945 0.092 Uiso 1 1 calc R . . C4 C 0.5337(3) 1.2437(3) 0.4206(2) 0.0843(8) Uani 1 1 d . . . H4A H 0.6395 1.3089 0.4622 0.101 Uiso 1 1 calc R . . C5 C 0.4396(3) 1.1514(3) 0.45984(19) 0.0738(7) Uani 1 1 d . . . H5A H 0.4845 1.1586 0.5282 0.089 Uiso 1 1 calc R . . C6 C 0.2826(3) 1.0493(2) 0.40306(17) 0.0571(6) Uani 1 1 d . . . C7 C 0.2249(2) 1.0419(2) 0.30046(16) 0.0512(5) Uani 1 1 d . . . C8 C 0.3147(3) 1.1388(2) 0.26099(18) 0.0579(6) Uani 1 1 d . . . C9 C -0.0105(2) 0.7062(2) 0.26065(14) 0.0478(5) Uani 1 1 d . . . C10 C -0.1164(2) 0.6322(2) 0.30520(15) 0.0533(6) Uani 1 1 d . . . C11 C -0.0745(3) 0.5259(2) 0.34684(15) 0.0581(6) Uani 1 1 d . . . H11A H -0.1454 0.4803 0.3774 0.070 Uiso 1 1 calc R . . C12 C 0.0691(3) 0.4853(2) 0.34446(16) 0.0606(6) Uani 1 1 d . . . C13 C 0.1711(3) 0.5565(2) 0.29886(16) 0.0601(6) Uani 1 1 d . . . H13A H 0.2675 0.5303 0.2954 0.072 Uiso 1 1 calc R . . C14 C 0.1365(2) 0.6646(2) 0.25811(15) 0.0530(6) Uani 1 1 d . . . C15 C 0.2586(3) 0.7312(2) 0.20985(18) 0.0716(7) Uani 1 1 d . . . H15A H 0.3254 0.6704 0.1969 0.107 Uiso 1 1 calc R . . H15B H 0.3347 0.8210 0.2543 0.107 Uiso 1 1 calc R . . H15C H 0.1934 0.7448 0.1476 0.107 Uiso 1 1 calc R . . C16 C 0.1084(3) 0.3671(3) 0.38775(19) 0.0870(8) Uani 1 1 d . . . H16A H 0.0292 0.3374 0.4212 0.130 Uiso 1 1 calc R . . H16B H 0.2246 0.3996 0.4351 0.130 Uiso 1 1 calc R . . H16C H 0.0964 0.2888 0.3345 0.130 Uiso 1 1 calc R . . C17 C -0.2768(3) 0.6670(3) 0.31356(19) 0.0732(7) Uani 1 1 d . . . H17A H -0.3376 0.5986 0.3395 0.110 Uiso 1 1 calc R . . H17B H -0.3506 0.6647 0.2483 0.110 Uiso 1 1 calc R . . H17C H -0.2435 0.7596 0.3582 0.110 Uiso 1 1 calc R . . C18 C -0.2406(2) 0.7983(2) 0.12837(16) 0.0478(5) Uani 1 1 d . . . C19 C -0.3079(3) 0.6936(2) 0.03633(17) 0.0537(6) Uani 1 1 d . . . C20 C -0.4703(3) 0.6776(2) -0.03197(17) 0.0655(6) Uani 1 1 d . . . H20A H -0.5138 0.6072 -0.0924 0.079 Uiso 1 1 calc R . . C21 C -0.5686(3) 0.7632(3) -0.01266(18) 0.0621(6) Uani 1 1 d . . . C22 C -0.4996(3) 0.8667(2) 0.07644(18) 0.0620(6) Uani 1 1 d . . . H22A H -0.5625 0.9268 0.0899 0.074 Uiso 1 1 calc R . . C23 C -0.3401(2) 0.8858(2) 0.14740(16) 0.0543(6) Uani 1 1 d . . . C24 C -0.2804(3) 0.9993(2) 0.24457(17) 0.0748(7) Uani 1 1 d . . . H24A H -0.3767 1.0283 0.2521 0.112 Uiso 1 1 calc R . . H24B H -0.1934 1.0791 0.2437 0.112 Uiso 1 1 calc R . . H24C H -0.2330 0.9630 0.2999 0.112 Uiso 1 1 calc R . . C25 C -0.7459(3) 0.7431(3) -0.08676(19) 0.0952(9) Uani 1 1 d . . . H25A H -0.7790 0.8267 -0.0715 0.143 Uiso 1 1 calc R . . H25B H -0.8283 0.6636 -0.0820 0.143 Uiso 1 1 calc R . . H25C H -0.7428 0.7263 -0.1538 0.143 Uiso 1 1 calc R . . C26 C -0.2031(3) 0.6021(2) 0.00724(17) 0.0731(7) Uani 1 1 d . . . H26A H -0.2782 0.5208 -0.0469 0.110 Uiso 1 1 calc R . . H26B H -0.1475 0.5720 0.0641 0.110 Uiso 1 1 calc R . . H26C H -0.1172 0.6557 -0.0139 0.110 Uiso 1 1 calc R . . C27 C 0.1827(3) 0.9614(3) 0.45310(16) 0.0754(7) Uani 1 1 d . . . H27A H 0.0648 0.9616 0.4305 0.113 Uiso 1 1 calc R . . H27B H 0.2332 1.0005 0.5247 0.113 Uiso 1 1 calc R . . H27C H 0.1864 0.8661 0.4360 0.113 Uiso 1 1 calc R . . 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 N 0.0487(10) 0.0545(11) 0.0483(11) 0.0135(9) 0.0134(9) 0.0131(9) B 0.0506(13) 0.0535(16) 0.0453(15) 0.0104(13) 0.0251(12) 0.0177(12) C1 0.0639(14) 0.0697(16) 0.0526(15) 0.0271(13) 0.0128(12) 0.0128(13) C2 0.0693(15) 0.0704(17) 0.0766(19) 0.0347(15) 0.0269(15) 0.0128(14) C3 0.0570(15) 0.0656(17) 0.095(2) 0.0154(16) 0.0190(15) 0.0082(13) C4 0.0586(15) 0.0743(19) 0.095(2) 0.0063(17) 0.0082(16) 0.0108(14) C5 0.0661(15) 0.0759(18) 0.0653(17) 0.0058(15) 0.0086(14) 0.0242(14) C6 0.0529(13) 0.0634(15) 0.0541(15) 0.0097(13) 0.0141(12) 0.0263(12) C7 0.0419(11) 0.0516(14) 0.0549(15) 0.0084(12) 0.0114(11) 0.0165(10) C8 0.0492(12) 0.0535(14) 0.0705(17) 0.0182(13) 0.0207(13) 0.0140(11) C9 0.0438(11) 0.0540(13) 0.0452(13) 0.0117(11) 0.0164(10) 0.0146(10) C10 0.0486(12) 0.0568(14) 0.0514(14) 0.0123(12) 0.0146(11) 0.0159(11) C11 0.0600(13) 0.0565(14) 0.0559(15) 0.0181(12) 0.0200(12) 0.0128(11) C12 0.0643(14) 0.0561(15) 0.0534(15) 0.0092(12) 0.0086(12) 0.0234(12) C13 0.0531(13) 0.0651(16) 0.0621(16) 0.0117(13) 0.0170(12) 0.0261(12) C14 0.0465(12) 0.0563(14) 0.0506(14) 0.0074(12) 0.0148(10) 0.0135(11) C15 0.0639(13) 0.0772(17) 0.0873(19) 0.0214(15) 0.0412(14) 0.0285(13) C16 0.1046(19) 0.0764(18) 0.0847(19) 0.0290(16) 0.0224(16) 0.0442(16) C17 0.0645(14) 0.0880(18) 0.0886(19) 0.0400(15) 0.0428(14) 0.0299(13) C18 0.0490(11) 0.0478(13) 0.0502(14) 0.0184(11) 0.0203(11) 0.0140(10) C19 0.0550(13) 0.0515(14) 0.0537(15) 0.0176(12) 0.0228(12) 0.0078(11) C20 0.0636(14) 0.0649(16) 0.0531(15) 0.0183(13) 0.0127(13) 0.0005(13) C21 0.0517(13) 0.0706(17) 0.0602(17) 0.0317(14) 0.0120(13) 0.0108(13) C22 0.0561(14) 0.0695(17) 0.0678(17) 0.0306(15) 0.0220(13) 0.0229(12) C23 0.0513(12) 0.0561(14) 0.0529(15) 0.0177(12) 0.0158(12) 0.0125(11) C24 0.0817(16) 0.0750(17) 0.0708(18) 0.0148(15) 0.0247(14) 0.0358(14) C25 0.0663(15) 0.112(2) 0.088(2) 0.0440(18) -0.0030(15) 0.0177(15) C26 0.0775(15) 0.0677(16) 0.0653(16) 0.0054(13) 0.0241(13) 0.0168(13) C27 0.0746(15) 0.099(2) 0.0493(15) 0.0152(14) 0.0188(13) 0.0289(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N C7 1.412(2) . ? N C1 1.422(2) . ? N B 1.457(3) . ? B C9 1.572(3) . ? B C18 1.574(3) . ? C1 C2 1.323(3) . ? C2 C8 1.428(3) . ? C3 C4 1.362(3) . ? C3 C8 1.386(3) . ? C4 C5 1.389(3) . ? C5 C6 1.385(3) . ? C6 C7 1.398(3) . ? C6 C27 1.504(3) . ? C7 C8 1.402(3) . ? C9 C10 1.405(3) . ? C9 C14 1.417(2) . ? C10 C11 1.390(3) . ? C10 C17 1.517(3) . ? C11 C12 1.383(3) . ? C12 C13 1.381(3) . ? C12 C16 1.504(3) . ? C13 C14 1.381(3) . ? C14 C15 1.508(3) . ? C18 C19 1.404(3) . ? C18 C23 1.405(3) . ? C19 C20 1.395(3) . ? C19 C26 1.513(3) . ? C20 C21 1.385(3) . ? C21 C22 1.369(3) . ? C21 C25 1.513(3) . ? C22 C23 1.385(3) . ? C23 C24 1.506(3) . ? 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 C7 N C1 105.32(16) . . ? C7 N B 134.71(18) . . ? C1 N B 118.48(18) . . ? N B C9 122.73(18) . . ? N B C18 113.85(18) . . ? C9 B C18 123.23(18) . . ? C2 C1 N 111.1(2) . . ? C1 C2 C8 108.1(2) . . ? C4 C3 C8 118.4(2) . . ? C3 C4 C5 120.2(2) . . ? C6 C5 C4 123.8(2) . . ? C5 C6 C7 115.1(2) . . ? C5 C6 C27 120.2(2) . . ? C7 C6 C27 124.57(19) . . ? C6 C7 C8 121.5(2) . . ? C6 C7 N 129.77(19) . . ? C8 C7 N 108.28(19) . . ? C3 C8 C7 120.9(2) . . ? C3 C8 C2 131.9(2) . . ? C7 C8 C2 107.09(19) . . ? C10 C9 C14 116.97(19) . . ? C10 C9 B 122.27(17) . . ? C14 C9 B 120.61(17) . . ? C11 C10 C9 120.71(18) . . ? C11 C10 C17 116.97(19) . . ? C9 C10 C17 122.28(19) . . ? C12 C11 C10 122.3(2) . . ? C13 C12 C11 116.8(2) . . ? C13 C12 C16 122.2(2) . . ? C11 C12 C16 121.0(2) . . ? C14 C13 C12 123.04(19) . . ? C13 C14 C9 120.17(19) . . ? C13 C14 C15 116.97(18) . . ? C9 C14 C15 122.8(2) . . ? C19 C18 C23 117.98(19) . . ? C19 C18 B 122.28(18) . . ? C23 C18 B 119.72(19) . . ? C20 C19 C18 119.8(2) . . ? C20 C19 C26 119.0(2) . . ? C18 C19 C26 121.06(19) . . ? C21 C20 C19 122.0(2) . . ? C22 C21 C20 117.4(2) . . ? C22 C21 C25 121.2(2) . . ? C20 C21 C25 121.5(2) . . ? C21 C22 C23 122.9(2) . . ? C22 C23 C18 119.9(2) . . ? C22 C23 C24 118.2(2) . . ? C18 C23 C24 121.92(19) . . ? _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.910 _refine_diff_density_max 0.144 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.031 # Attachment 'Comp5.CIF' data_cy604a _database_code_depnum_ccdc_archive 'CCDC 639178' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 5 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H32 B N' _chemical_formula_weight 441.40 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.4353(10) _cell_length_b 18.5158(15) _cell_length_c 11.9490(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.2680(10) _cell_angle_gamma 90.00 _cell_volume 2528.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.160 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.879 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17595 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0671 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.25 _reflns_number_total 5892 _reflns_number_gt 3391 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment Mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5892 _refine_ls_number_parameters 369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0945 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1230 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 0.905 _refine_ls_restrained_S_all 0.905 _refine_ls_shift/su_max 0.080 _refine_ls_shift/su_mean 0.001 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N N 0.26213(11) 0.09551(7) 0.81559(11) 0.0302(3) Uani 1 1 d . . . B B 0.30446(17) 0.12357(9) 0.92248(16) 0.0303(4) Uani 1 1 d . . . C1 C 0.33168(16) 0.06332(9) 0.73502(14) 0.0327(4) Uani 1 1 d . . . H1 H 0.4123(15) 0.0559(9) 0.7515(14) 0.039(5) Uiso 1 1 d . . . C2 C 0.26859(15) 0.04561(8) 0.64084(14) 0.0317(4) Uani 1 1 d . . . C3 C 0.04861(15) 0.07016(9) 0.58896(15) 0.0352(4) Uani 1 1 d . . . H3 H 0.0510(14) 0.0518(8) 0.5122(15) 0.037(5) Uiso 1 1 d . . . C4 C -0.05296(16) 0.09816(9) 0.62918(16) 0.0379(4) Uani 1 1 d . . . H4 H -0.1250(16) 0.1000(9) 0.5832(15) 0.048(5) Uiso 1 1 d . . . C5 C -0.05535(16) 0.12493(9) 0.73802(16) 0.0372(4) Uani 1 1 d . . . H5 H -0.1277(14) 0.1448(8) 0.7685(13) 0.033(4) Uiso 1 1 d . . . C6 C 0.04406(15) 0.12580(9) 0.80826(15) 0.0323(4) Uani 1 1 d . . . H6 H 0.0399(14) 0.1453(8) 0.8837(14) 0.034(4) Uiso 1 1 d . . . C7 C 0.14712(14) 0.09801(8) 0.76723(13) 0.0294(4) Uani 1 1 d . . . C8 C 0.14976(14) 0.06926(8) 0.65832(14) 0.0301(4) Uani 1 1 d . . . C9 C 0.21459(14) 0.13057(8) 1.01791(13) 0.0292(4) Uani 1 1 d . . . C10 C 0.18439(15) 0.19899(9) 1.06011(14) 0.0341(4) Uani 1 1 d . . . C11 C 0.10418(16) 0.20430(11) 1.14369(15) 0.0413(5) Uani 1 1 d . . . H11 H 0.0837(14) 0.2500(9) 1.1687(14) 0.041(5) Uiso 1 1 d . . . C12 C 0.05295(15) 0.14376(10) 1.18967(15) 0.0423(5) Uani 1 1 d . . . C13 C 0.08272(16) 0.07663(10) 1.14847(15) 0.0392(4) Uani 1 1 d . . . H13 H 0.0474(14) 0.0340(9) 1.1778(14) 0.037(5) Uiso 1 1 d . . . C14 C 0.16073(14) 0.06890(9) 1.06260(14) 0.0331(4) Uani 1 1 d . . . C15 C 0.18583(16) -0.00641(9) 1.02029(15) 0.0421(5) Uani 1 1 d . . . H15A H 0.1809 -0.0410 1.0820 0.063 Uiso 1 1 calc R . . H15B H 0.2646 -0.0078 0.9909 0.063 Uiso 1 1 calc R . . H15C H 0.1282 -0.0191 0.9606 0.063 Uiso 1 1 calc R . . C16 C -0.03462(19) 0.15034(12) 1.28121(18) 0.0630(6) Uani 1 1 d . . . H16A H -0.0966 0.1843 1.2575 0.095 Uiso 1 1 calc R . . H16B H 0.0052 0.1681 1.3499 0.095 Uiso 1 1 calc R . . H16C H -0.0691 0.1029 1.2953 0.095 Uiso 1 1 calc R . . C17 C 0.23249(17) 0.26683(9) 1.00866(16) 0.0444(5) Uani 1 1 d . . . H17A H 0.2097 0.3089 1.0526 0.067 Uiso 1 1 calc R . . H17B H 0.2009 0.2718 0.9316 0.067 Uiso 1 1 calc R . . H17C H 0.3180 0.2638 1.0084 0.067 Uiso 1 1 calc R . . C18 C 0.43717(14) 0.14765(8) 0.93662(14) 0.0305(4) Uani 1 1 d . . . C19 C 0.50805(15) 0.12541(8) 1.03018(14) 0.0327(4) Uani 1 1 d . . . C20 C 0.62080(16) 0.15171(10) 1.04586(16) 0.0387(4) Uani 1 1 d . . . H20 H 0.6679(15) 0.1350(8) 1.1073(14) 0.037(5) Uiso 1 1 d . . . C21 C 0.66919(16) 0.20086(10) 0.97368(16) 0.0420(5) Uani 1 1 d . . . C22 C 0.59963(16) 0.22320(10) 0.88274(16) 0.0416(5) Uani 1 1 d . . . H22 H 0.6330(14) 0.2574(8) 0.8324(14) 0.038(5) Uiso 1 1 d . . . C23 C 0.48594(15) 0.19800(9) 0.86247(13) 0.0346(4) Uani 1 1 d . . . C24 C 0.41754(17) 0.22953(10) 0.76259(15) 0.0480(5) Uani 1 1 d . . . H24A H 0.4515 0.2762 0.7427 0.072 Uiso 1 1 calc R . . H24B H 0.3357 0.2364 0.7817 0.072 Uiso 1 1 calc R . . H24C H 0.4213 0.1964 0.6989 0.072 Uiso 1 1 calc R . . C25 C 0.79157(17) 0.22972(12) 0.99538(19) 0.0630(6) Uani 1 1 d . . . H25A H 0.8470 0.1894 1.0007 0.095 Uiso 1 1 calc R . . H25B H 0.7949 0.2570 1.0658 0.095 Uiso 1 1 calc R . . H25C H 0.8123 0.2616 0.9337 0.095 Uiso 1 1 calc R . . C26 C 0.46431(16) 0.07251(10) 1.11476(15) 0.0437(5) Uani 1 1 d . . . H26A H 0.5270 0.0619 1.1706 0.066 Uiso 1 1 calc R . . H26B H 0.4401 0.0278 1.0767 0.066 Uiso 1 1 calc R . . H26C H 0.3974 0.0934 1.1520 0.066 Uiso 1 1 calc R . . C27 C 0.30861(14) 0.00640(9) 0.54157(14) 0.0326(4) Uani 1 1 d . . . C28 C 0.37108(16) -0.05777(10) 0.55323(17) 0.0415(5) Uani 1 1 d . . . H28 H 0.3924(16) -0.0759(9) 0.6320(16) 0.052(5) Uiso 1 1 d . . . C29 C 0.40273(18) -0.09683(11) 0.45996(18) 0.0480(5) Uani 1 1 d . . . H29 H 0.4501(16) -0.1413(10) 0.4715(16) 0.062(6) Uiso 1 1 d . . . C30 C 0.37184(16) -0.07259(11) 0.35367(17) 0.0452(5) Uani 1 1 d . . . H30 H 0.3915(15) -0.1024(9) 0.2851(16) 0.050(5) Uiso 1 1 d . . . C31 C 0.31174(16) -0.00833(11) 0.34091(16) 0.0423(5) Uani 1 1 d . . . H31 H 0.2915(14) 0.0091(9) 0.2654(15) 0.044(5) Uiso 1 1 d . . . C32 C 0.28057(16) 0.03108(10) 0.43333(15) 0.0374(4) Uani 1 1 d . . . H32 H 0.2386(14) 0.0772(9) 0.4225(14) 0.038(5) Uiso 1 1 d . . . 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 N 0.0306(8) 0.0320(7) 0.0279(8) -0.0021(6) 0.0010(6) 0.0014(6) B 0.0396(11) 0.0216(9) 0.0296(11) 0.0027(8) -0.0010(9) 0.0027(8) C1 0.0311(10) 0.0349(9) 0.0323(10) 0.0001(7) 0.0040(8) 0.0024(7) C2 0.0362(10) 0.0306(9) 0.0283(9) 0.0009(7) 0.0012(8) -0.0024(7) C3 0.0387(11) 0.0363(9) 0.0304(10) -0.0002(8) -0.0015(8) -0.0088(8) C4 0.0322(11) 0.0414(10) 0.0395(11) 0.0043(9) -0.0066(9) -0.0066(8) C5 0.0319(10) 0.0369(10) 0.0430(12) 0.0035(8) 0.0040(9) -0.0014(8) C6 0.0331(10) 0.0336(9) 0.0305(10) 0.0007(8) 0.0031(8) -0.0014(7) C7 0.0313(9) 0.0260(8) 0.0306(9) 0.0025(7) -0.0006(8) -0.0027(7) C8 0.0349(10) 0.0258(8) 0.0295(9) 0.0010(7) 0.0013(8) -0.0054(7) C9 0.0292(9) 0.0318(9) 0.0262(9) -0.0029(7) -0.0041(7) 0.0019(7) C10 0.0370(10) 0.0342(9) 0.0306(10) -0.0060(8) -0.0046(8) 0.0031(7) C11 0.0439(11) 0.0421(11) 0.0378(11) -0.0117(9) 0.0013(9) 0.0100(9) C12 0.0367(11) 0.0574(12) 0.0331(11) -0.0031(9) 0.0040(9) 0.0079(9) C13 0.0355(10) 0.0453(11) 0.0370(11) 0.0047(9) 0.0019(9) -0.0009(8) C14 0.0334(10) 0.0365(9) 0.0293(9) -0.0018(7) -0.0009(8) 0.0002(7) C15 0.0507(12) 0.0336(10) 0.0422(11) -0.0002(8) 0.0054(9) -0.0050(8) C16 0.0597(14) 0.0816(15) 0.0493(13) -0.0025(12) 0.0216(11) 0.0122(12) C17 0.0545(12) 0.0320(10) 0.0468(12) -0.0057(8) 0.0026(10) 0.0048(8) C18 0.0338(9) 0.0298(8) 0.0279(9) -0.0046(7) 0.0018(8) 0.0021(7) C19 0.0354(10) 0.0311(9) 0.0315(10) -0.0051(7) 0.0012(8) 0.0038(7) C20 0.0351(11) 0.0436(10) 0.0370(11) -0.0074(9) -0.0050(9) 0.0058(8) C21 0.0362(11) 0.0455(11) 0.0443(12) -0.0117(9) 0.0037(9) -0.0053(8) C22 0.0431(12) 0.0401(10) 0.0422(12) -0.0016(9) 0.0100(10) -0.0083(9) C23 0.0396(10) 0.0339(9) 0.0305(10) -0.0016(8) 0.0027(8) 0.0007(8) C24 0.0544(13) 0.0481(11) 0.0413(12) 0.0117(9) 0.0009(10) -0.0055(9) C25 0.0405(12) 0.0793(16) 0.0693(16) -0.0072(12) 0.0008(11) -0.0160(11) C26 0.0439(11) 0.0484(11) 0.0380(11) 0.0087(9) -0.0064(9) 0.0019(9) C27 0.0333(10) 0.0350(9) 0.0296(10) -0.0032(7) 0.0030(8) -0.0059(7) C28 0.0445(11) 0.0438(11) 0.0361(11) -0.0011(9) 0.0014(9) 0.0036(9) C29 0.0455(12) 0.0475(12) 0.0514(14) -0.0107(10) 0.0087(10) 0.0058(9) C30 0.0364(11) 0.0590(13) 0.0412(12) -0.0162(10) 0.0117(9) -0.0092(9) C31 0.0390(11) 0.0595(13) 0.0287(11) -0.0006(9) 0.0046(9) -0.0112(9) C32 0.0378(11) 0.0400(10) 0.0346(11) 0.0003(8) 0.0040(8) -0.0029(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N C1 1.406(2) . ? N C7 1.416(2) . ? N B 1.444(2) . ? B C9 1.570(2) . ? B C18 1.584(2) . ? C1 C2 1.353(2) . ? C2 C8 1.451(2) . ? C2 C27 1.479(2) . ? C3 C4 1.376(2) . ? C3 C8 1.396(2) . ? C4 C5 1.393(3) . ? C5 C6 1.386(2) . ? C6 C7 1.393(2) . ? C7 C8 1.408(2) . ? C9 C10 1.411(2) . ? C9 C14 1.412(2) . ? C10 C11 1.386(2) . ? C10 C17 1.512(2) . ? C11 C12 1.388(3) . ? C12 C13 1.384(2) . ? C12 C16 1.517(2) . ? C13 C14 1.393(2) . ? C14 C15 1.515(2) . ? C18 C23 1.416(2) . ? C18 C19 1.416(2) . ? C19 C20 1.384(2) . ? C19 C26 1.507(2) . ? C20 C21 1.384(3) . ? C21 C22 1.384(3) . ? C21 C25 1.511(3) . ? C22 C23 1.393(2) . ? C23 C24 1.518(2) . ? C27 C28 1.390(2) . ? C27 C32 1.397(2) . ? C28 C29 1.389(2) . ? C29 C30 1.380(3) . ? C30 C31 1.380(3) . ? C31 C32 1.382(2) . ? 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 C1 N C7 106.02(13) . . ? C1 N B 125.40(14) . . ? C7 N B 128.48(14) . . ? N B C9 117.76(15) . . ? N B C18 118.79(15) . . ? C9 B C18 123.43(15) . . ? C2 C1 N 112.02(15) . . ? C1 C2 C8 106.20(14) . . ? C1 C2 C27 127.92(15) . . ? C8 C2 C27 125.80(15) . . ? C4 C3 C8 119.22(17) . . ? C3 C4 C5 120.54(18) . . ? C6 C5 C4 121.57(17) . . ? C5 C6 C7 117.88(17) . . ? C6 C7 C8 120.97(16) . . ? C6 C7 N 130.81(15) . . ? C8 C7 N 108.14(14) . . ? C3 C8 C7 119.78(16) . . ? C3 C8 C2 132.61(16) . . ? C7 C8 C2 107.56(14) . . ? C10 C9 C14 118.30(15) . . ? C10 C9 B 120.66(14) . . ? C14 C9 B 121.03(14) . . ? C11 C10 C9 119.96(16) . . ? C11 C10 C17 119.73(15) . . ? C9 C10 C17 120.16(15) . . ? C10 C11 C12 121.97(17) . . ? C13 C12 C11 118.08(17) . . ? C13 C12 C16 120.48(18) . . ? C11 C12 C16 121.43(17) . . ? C12 C13 C14 121.85(17) . . ? C13 C14 C9 119.80(16) . . ? C13 C14 C15 118.40(15) . . ? C9 C14 C15 121.80(15) . . ? C23 C18 C19 117.28(15) . . ? C23 C18 B 121.20(15) . . ? C19 C18 B 121.22(14) . . ? C20 C19 C18 120.38(16) . . ? C20 C19 C26 118.03(16) . . ? C18 C19 C26 121.58(15) . . ? C19 C20 C21 122.70(18) . . ? C22 C21 C20 117.00(17) . . ? C22 C21 C25 121.91(18) . . ? C20 C21 C25 121.07(18) . . ? C21 C22 C23 122.66(17) . . ? C22 C23 C18 119.98(17) . . ? C22 C23 C24 117.13(16) . . ? C18 C23 C24 122.82(16) . . ? C28 C27 C32 118.06(16) . . ? C28 C27 C2 120.88(15) . . ? C32 C27 C2 121.00(15) . . ? C29 C28 C27 120.92(19) . . ? C30 C29 C28 120.27(19) . . ? C29 C30 C31 119.38(18) . . ? C30 C31 C32 120.67(19) . . ? C31 C32 C27 120.67(18) . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 0.277 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.037