# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Kiviniemi, Sari' 'Nissinen Maija' 'Alaviuhkola Terhi' 'Pursiainen Jouni' 'Rissanen, Kari' _publ_contact_author_name 'Mrs Sari Kiviniemi' _publ_contact_author_address ; Mrs Sari Kiviniemi Department of Chemistry University of Oulu PO Box 3000 Oulu FIN-90014 FINLAND ; data_Comp3 _database_code_CSD 156976 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H28 B N' _chemical_formula_weight 413.34 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 C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 16.1480(5) _cell_length_b 10.2577(3) _cell_length_c 13.9283(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.572(2) _cell_angle_gamma 90.00 _cell_volume 2304.78(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173.0(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _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 1.191 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min 0.9735 _exptl_absorpt_correction_T_max 0.9866 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(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 'nonius kappaccd' _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 5895 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2149 _reflns_number_gt 1876 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0436P)^2^+1.2834P] 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 SHELXL _refine_ls_extinction_coef 0.018(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2149 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 C1 C 0.11720(8) 0.12483(13) 0.74433(9) 0.0282(3) Uani 1 1 d . . . C2 C 0.08772(8) 0.17617(16) 0.82957(11) 0.0410(4) Uani 1 1 d . . . H2 H 0.1113 0.1457 0.8891 0.049 Uiso 1 1 calc R . . C3 C 0.02569(10) 0.26928(18) 0.83083(14) 0.0551(5) Uani 1 1 d . . . H3 H 0.0077 0.3010 0.8905 0.066 Uiso 1 1 calc R . . C4 C -0.01019(10) 0.31626(17) 0.74600(15) 0.0574(5) Uani 1 1 d . . . H4 H -0.0532 0.3794 0.7466 0.069 Uiso 1 1 calc R . . C5 C 0.01767(9) 0.26947(16) 0.65974(13) 0.0497(5) Uani 1 1 d . . . H5 H -0.0056 0.3018 0.6006 0.060 Uiso 1 1 calc R . . C6 C 0.07958(8) 0.17531(14) 0.65986(10) 0.0358(4) Uani 1 1 d . . . H6 H 0.0971 0.1438 0.5999 0.043 Uiso 1 1 calc R . . C7 C 0.24774(11) 0.0000 0.83620(12) 0.0271(4) Uani 1 2 d S . . C8 C 0.28133(8) 0.11533(14) 0.87456(9) 0.0340(4) Uani 1 1 d . . . H8 H 0.2606 0.1963 0.8507 0.041 Uiso 1 1 calc R . . C9 C 0.34416(9) 0.11599(16) 0.94654(10) 0.0393(4) Uani 1 1 d . . . H9 H 0.3653 0.1965 0.9709 0.047 Uiso 1 1 calc R . . C10 C 0.37581(12) 0.0000 0.98251(14) 0.0395(5) Uani 1 2 d S . . H10 H 0.4188 0.0000 1.0314 0.047 Uiso 1 2 calc SR . . C13 C 0.23971(10) 0.0000 0.65084(12) 0.0246(4) Uani 1 2 d S . . C14 C 0.27023(8) 0.11538(13) 0.61178(9) 0.0290(3) Uani 1 1 d . . . H14 H 0.2517 0.1964 0.6359 0.035 Uiso 1 1 calc R . . C15 C 0.32659(8) 0.11588(14) 0.53906(9) 0.0334(4) Uani 1 1 d . . . H15 H 0.3454 0.1964 0.5143 0.040 Uiso 1 1 calc R . . C16 C 0.35539(11) 0.0000 0.50259(13) 0.0335(5) Uani 1 2 d S . . H16 H 0.3943 0.0000 0.4534 0.040 Uiso 1 2 calc SR . . C26 C -0.09654(12) 0.0000 0.77148(14) 0.0405(5) Uani 1 2 d S . . H26 H -0.0398 0.0000 0.7560 0.049 Uiso 1 2 calc SR . . C27 C -0.11748(13) 0.0000 0.86590(15) 0.0464(6) Uani 1 2 d S . . H27 H -0.0752 0.0000 0.9156 0.056 Uiso 1 2 calc SR . . C28 C -0.19886(14) 0.0000 0.88856(16) 0.0472(6) Uani 1 2 d S . . H28 H -0.2139 0.0000 0.9537 0.057 Uiso 1 2 calc SR . . C29 C -0.25885(14) 0.0000 0.81493(17) 0.0566(7) Uani 1 2 d S . . H29 H -0.3159 0.0000 0.8289 0.068 Uiso 1 2 calc SR . . C30 C -0.23590(13) 0.0000 0.72193(16) 0.0472(6) Uani 1 2 d S . . H30 H -0.2772 0.0000 0.6712 0.057 Uiso 1 2 calc SR . . C31 C -0.13243(16) 0.0000 0.60027(15) 0.0453(6) Uani 1 2 d S . . H31A H -0.1771(19) 0.0000 0.559(2) 0.068 Uiso 1 2 d S . . H31B H -0.0967(12) -0.0680(19) 0.5900(14) 0.068 Uiso 1 1 d . . . B1 B 0.18066(13) 0.0000 0.74409(14) 0.0255(5) Uani 1 2 d S . . N25 N -0.15554(10) 0.0000 0.70139(11) 0.0315(4) Uani 1 2 d S . . 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 C1 0.0229(6) 0.0302(7) 0.0315(7) -0.0020(5) 0.0011(5) -0.0033(5) C2 0.0301(7) 0.0524(10) 0.0403(8) -0.0148(7) -0.0005(6) 0.0037(7) C3 0.0351(9) 0.0595(11) 0.0707(11) -0.0302(9) 0.0027(8) 0.0073(8) C4 0.0330(8) 0.0384(9) 0.1009(15) -0.0085(9) 0.0029(9) 0.0095(7) C5 0.0321(8) 0.0448(9) 0.0718(11) 0.0192(8) -0.0006(8) 0.0051(7) C6 0.0276(7) 0.0399(8) 0.0401(8) 0.0081(6) 0.0024(6) 0.0023(6) C7 0.0228(9) 0.0384(11) 0.0203(9) 0.000 0.0040(7) 0.000 C8 0.0313(7) 0.0410(8) 0.0294(7) 0.0015(6) -0.0016(6) -0.0052(6) C9 0.0328(8) 0.0534(10) 0.0314(7) -0.0030(7) -0.0022(6) -0.0108(7) C10 0.0236(10) 0.0694(15) 0.0253(10) 0.000 -0.0021(8) 0.000 C13 0.0215(9) 0.0304(10) 0.0213(9) 0.000 -0.0049(7) 0.000 C14 0.0270(7) 0.0295(7) 0.0304(7) -0.0011(5) -0.0001(5) -0.0017(5) C15 0.0285(7) 0.0406(8) 0.0311(7) 0.0057(6) 0.0009(6) -0.0061(6) C16 0.0219(9) 0.0525(13) 0.0261(9) 0.000 0.0018(7) 0.000 C26 0.0270(10) 0.0603(14) 0.0340(11) 0.000 0.0000(8) 0.000 C27 0.0370(12) 0.0706(16) 0.0311(11) 0.000 -0.0034(9) 0.000 C28 0.0428(13) 0.0662(15) 0.0330(11) 0.000 0.0066(9) 0.000 C29 0.0317(12) 0.095(2) 0.0436(13) 0.000 0.0070(10) 0.000 C30 0.0303(11) 0.0729(16) 0.0379(12) 0.000 -0.0032(9) 0.000 C31 0.0408(13) 0.0676(17) 0.0278(11) 0.000 0.0030(9) 0.000 B1 0.0252(10) 0.0297(11) 0.0213(10) 0.000 -0.0007(8) 0.000 N25 0.0307(9) 0.0354(9) 0.0283(8) 0.000 0.0000(7) 0.000 _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 C1 C6 1.3991(18) . ? C1 C2 1.4015(19) . ? C1 B1 1.6402(18) . ? C2 C3 1.385(2) . ? C3 C4 1.379(3) . ? C4 C5 1.387(3) . ? C5 C6 1.390(2) . ? C7 C8 1.3976(17) 6 ? C7 C8 1.3976(17) . ? C7 B1 1.641(3) . ? C8 C9 1.3940(19) . ? C9 C10 1.3801(18) . ? C10 C9 1.3801(18) 6 ? C13 C14 1.4013(16) 6 ? C13 C14 1.4013(16) . ? C13 B1 1.645(3) . ? C14 C15 1.3917(19) . ? C15 C16 1.3814(17) . ? C16 C15 1.3814(17) 6 ? C26 N25 1.333(2) . ? C26 C27 1.373(3) . ? C27 C28 1.365(3) . ? C28 C29 1.379(3) . ? C29 C30 1.363(3) . ? C30 N25 1.341(3) . ? C31 N25 1.473(3) . ? B1 C1 1.6402(18) 6 ? 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 C6 C1 C2 114.97(12) . . ? C6 C1 B1 122.34(12) . . ? C2 C1 B1 122.08(13) . . ? C3 C2 C1 122.90(15) . . ? C4 C3 C2 120.43(16) . . ? C3 C4 C5 118.74(15) . . ? C4 C5 C6 120.03(15) . . ? C5 C6 C1 122.91(14) . . ? C8 C7 C8 115.66(16) 6 . ? C8 C7 B1 122.01(8) 6 . ? C8 C7 B1 122.01(8) . . ? C9 C8 C7 122.45(14) . . ? C10 C9 C8 120.17(14) . . ? C9 C10 C9 119.10(17) 6 . ? C14 C13 C14 115.26(16) 6 . ? C14 C13 B1 122.20(8) 6 . ? C14 C13 B1 122.20(8) . . ? C15 C14 C13 122.58(13) . . ? C16 C15 C14 120.43(13) . . ? C15 C16 C15 118.73(17) . 6 ? N25 C26 C27 120.20(18) . . ? C28 C27 C26 120.2(2) . . ? C27 C28 C29 118.7(2) . . ? C30 C29 C28 119.7(2) . . ? N25 C30 C29 120.6(2) . . ? C1 B1 C1 102.65(14) 6 . ? C1 B1 C7 112.88(10) 6 . ? C1 B1 C7 112.88(10) . . ? C1 B1 C13 112.70(10) 6 . ? C1 B1 C13 112.70(10) . . ? C7 B1 C13 103.39(14) . . ? C26 N25 C30 120.68(17) . . ? C26 N25 C31 119.78(17) . . ? C30 N25 C31 119.54(18) . . ? 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 C6 C1 C2 C3 0.4(2) . . . . ? B1 C1 C2 C3 -170.88(14) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C3 C4 C5 C6 1.1(3) . . . . ? C4 C5 C6 C1 -0.9(2) . . . . ? C2 C1 C6 C5 0.1(2) . . . . ? B1 C1 C6 C5 171.34(13) . . . . ? C8 C7 C8 C9 -0.1(2) 6 . . . ? B1 C7 C8 C9 -173.62(14) . . . . ? C7 C8 C9 C10 0.2(2) . . . . ? C8 C9 C10 C9 -0.3(3) . . . 6 ? C14 C13 C14 C15 0.3(2) 6 . . . ? B1 C13 C14 C15 173.60(13) . . . . ? C13 C14 C15 C16 -0.5(2) . . . . ? C14 C15 C16 C15 0.6(3) . . . 6 ? N25 C26 C27 C28 0.0 . . . . ? C26 C27 C28 C29 0.0 . . . . ? C27 C28 C29 C30 0.0 . . . . ? C28 C29 C30 N25 0.0 . . . . ? C6 C1 B1 C1 -84.83(16) . . . 6 ? C2 C1 B1 C1 85.79(16) . . . 6 ? C6 C1 B1 C7 153.35(13) . . . . ? C2 C1 B1 C7 -36.03(18) . . . . ? C6 C1 B1 C13 36.67(18) . . . . ? C2 C1 B1 C13 -152.71(13) . . . . ? C8 C7 B1 C1 35.5(2) 6 . . 6 ? C8 C7 B1 C1 -151.38(13) . . . 6 ? C8 C7 B1 C1 151.38(13) 6 . . . ? C8 C7 B1 C1 -35.5(2) . . . . ? C8 C7 B1 C13 -86.55(14) 6 . . . ? C8 C7 B1 C13 86.55(14) . . . . ? C14 C13 B1 C1 -35.8(2) 6 . . 6 ? C14 C13 B1 C1 151.37(13) . . . 6 ? C14 C13 B1 C1 -151.37(13) 6 . . . ? C14 C13 B1 C1 35.8(2) . . . . ? C14 C13 B1 C7 86.43(14) 6 . . . ? C14 C13 B1 C7 -86.43(14) . . . . ? C27 C26 N25 C30 0.0 . . . . ? C27 C26 N25 C31 180.0 . . . . ? C29 C30 N25 C26 0.0 . . . . ? C29 C30 N25 C31 180.0 . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.207 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.033 #===END data_comp2 _database_code_CSD 156977 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H30 B N3' _chemical_formula_weight 443.38 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 P21/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 13.0490(5) _cell_length_b 9.9316(4) _cell_length_c 19.1286(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.065(2) _cell_angle_gamma 90.00 _cell_volume 2478.59(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173.0(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description cubic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min 0.9795 _exptl_absorpt_correction_T_max 0.9795 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(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 'nonius kappaccd' _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 7917 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.05 _reflns_number_total 4635 _reflns_number_gt 3961 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'shelxs-97 (Sheldrick, 1997)' _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^)+(0.0564P)^2^+3.4347P] 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 4635 _refine_ls_number_parameters 369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1008 _refine_ls_R_factor_gt 0.0872 _refine_ls_wR_factor_ref 0.2064 _refine_ls_wR_factor_gt 0.1994 _refine_ls_goodness_of_fit_ref 1.163 _refine_ls_restrained_S_all 1.163 _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 C1 C 0.2357(2) 0.3782(3) 0.14719(14) 0.0353(7) Uani 1 1 d . . . C1B C 0.7278(2) 0.6213(3) 0.35162(13) 0.0319(6) Uani 1 1 d . . . C2 C 0.1358(3) 0.4273(3) 0.13849(16) 0.0444(8) Uani 1 1 d . . . H2 H 0.0954 0.3945 0.1003 0.053 Uiso 1 1 calc R . . C2B C 0.7782(3) 0.5692(3) 0.29370(15) 0.0441(8) Uani 1 1 d . . . H2B H 0.8458 0.5989 0.2843 0.053 Uiso 1 1 calc R . . C3 C 0.0924(4) 0.5220(4) 0.18284(19) 0.0680(12) Uani 1 1 d . . . H3 H 0.0245 0.5529 0.1741 0.082 Uiso 1 1 calc R . . C3B C 0.7316(3) 0.4744(3) 0.24908(15) 0.0555(10) Uani 1 1 d . . . H3B H 0.7681 0.4410 0.2102 0.067 Uiso 1 1 calc R . . C4 C 0.1469(5) 0.5702(4) 0.2384(2) 0.0873(18) Uani 1 1 d . . . H4 H 0.1174 0.6338 0.2692 0.105 Uiso 1 1 calc R . . C4B C 0.6339(3) 0.4292(3) 0.26079(17) 0.0572(10) Uani 1 1 d . . . H4B H 0.6024 0.3655 0.2302 0.069 Uiso 1 1 calc R . . C5 C 0.2446(5) 0.5260(4) 0.24940(17) 0.0814(17) Uani 1 1 d . . . H5 H 0.2832 0.5601 0.2881 0.098 Uiso 1 1 calc R . . C5B C 0.5831(3) 0.4775(3) 0.31731(17) 0.0492(9) Uani 1 1 d . . . H5B H 0.5157 0.4469 0.3264 0.059 Uiso 1 1 calc R . . C6 C 0.2902(3) 0.4309(3) 0.20470(15) 0.0534(10) Uani 1 1 d . . . H6 H 0.3587 0.4023 0.2138 0.064 Uiso 1 1 calc R . . C6B C 0.6293(2) 0.5712(3) 0.36157(15) 0.0376(7) Uani 1 1 d . . . H6B H 0.5920 0.6026 0.4005 0.045 Uiso 1 1 calc R . . C7 C 0.4020(4) 0.2500 0.0930(2) 0.0475(12) Uani 1 2 d S . . C7B C 0.8978(3) 0.7500 0.4047(2) 0.0376(10) Uani 1 2 d S . . C8 C 0.4584(3) 0.3696(6) 0.08630(17) 0.0722(14) Uani 1 1 d . . . H8 H 0.4236 0.4536 0.0877 0.087 Uiso 1 1 calc R . . C8B C 0.9547(3) 0.6309(4) 0.41101(17) 0.0519(9) Uani 1 1 d . . . H8B H 0.9198 0.5470 0.4089 0.062 Uiso 1 1 calc R . . C9 C 0.5637(4) 0.3680(10) 0.0777(2) 0.130(3) Uani 1 1 d . . . H9 H 0.5995 0.4511 0.0747 0.156 Uiso 1 1 calc R . . C9B C 1.0595(3) 0.6315(6) 0.42015(19) 0.0746(14) Uani 1 1 d . . . H9B H 1.0951 0.5483 0.4239 0.090 Uiso 1 1 calc R . . C10 C 0.6176(7) 0.2500 0.0732(4) 0.171(8) Uani 1 2 d S . . H10 H 0.6897 0.2500 0.0673 0.205 Uiso 1 2 calc SR . . C10B C 1.1138(4) 0.7500 0.4240(3) 0.085(3) Uani 1 2 d S . . H10B H 1.1863 0.7500 0.4291 0.103 Uiso 1 2 calc SR . . C13 C 0.2304(3) 0.2500 0.02142(19) 0.0281(8) Uani 1 2 d S . . C13B C 0.7318(3) 0.7500 0.47722(19) 0.0280(8) Uani 1 2 d S . . C14 C 0.2119(2) 0.3689(3) -0.01606(14) 0.0353(7) Uani 1 1 d . . . H14 H 0.2258 0.4526 0.0062 0.042 Uiso 1 1 calc R . . C14B C 0.7159(2) 0.6310(3) 0.51517(14) 0.0334(7) Uani 1 1 d . . . H14B H 0.7275 0.5472 0.4927 0.040 Uiso 1 1 calc R . . C15 C 0.1741(3) 0.3695(3) -0.08442(15) 0.0444(8) Uani 1 1 d . . . H15 H 0.1621 0.4526 -0.1077 0.053 Uiso 1 1 calc R . . C15B C 0.6840(2) 0.6304(3) 0.58375(15) 0.0407(7) Uani 1 1 d . . . H15B H 0.6739 0.5472 0.6072 0.049 Uiso 1 1 calc R . . C16 C 0.1539(4) 0.2500 -0.1186(2) 0.0469(12) Uani 1 2 d S . . H16 H 0.1264 0.2500 -0.1650 0.056 Uiso 1 2 calc SR . . C16B C 0.6669(4) 0.7500 0.6183(2) 0.0439(11) Uani 1 2 d S . . H16B H 0.6436 0.7500 0.6651 0.053 Uiso 1 2 calc SR . . C29 C 0.5392(4) 0.2500 -0.2027(2) 0.0489(12) Uani 1 2 d S . . H29 H 0.5815 0.2500 -0.2425 0.059 Uiso 1 2 calc SR . . C29B C 1.0473(4) 0.7500 0.7027(2) 0.0490(12) Uani 1 2 d S . . H29B H 1.0904 0.7500 0.7433 0.059 Uiso 1 2 calc SR . . N27 N 0.4085(4) 0.2500 -0.1361(3) 0.0762(15) Uani 1 2 d S . . H27 H 0.3449 0.2500 -0.1216 0.091 Uiso 1 2 calc SR . . N27B N 0.9158(3) 0.7500 0.6329(2) 0.0611(12) Uani 1 2 d S . . H27B H 0.8519 0.7500 0.6173 0.073 Uiso 1 2 calc SR . . C26 C 0.4917(4) 0.2500 -0.0962(3) 0.0736(19) Uani 1 2 d S . . H26 H 0.4927 0.2500 -0.0465 0.088 Uiso 1 2 calc SR . . C26B C 0.9975(4) 0.7500 0.5939(3) 0.0536(13) Uani 1 2 d S . . H26B H 0.9972 0.7500 0.5443 0.064 Uiso 1 2 calc SR . . C30 C 0.6805(4) 0.2500 -0.1108(3) 0.0405(10) Uani 1 2 d S . . H30A H 0.721(3) 0.320(4) -0.1293(19) 0.061 Uiso 1 1 d . . . H30B H 0.686(4) 0.2500 -0.057(3) 0.061 Uiso 1 2 d S . . C30B C 1.1862(4) 0.7500 0.6114(3) 0.0407(10) Uani 1 2 d S . . H30D H 1.220(3) 0.672(4) 0.6310(19) 0.061 Uiso 1 1 d . . . H30E H 1.189(4) 0.7500 0.559(3) 0.061 Uiso 1 2 d S . . C51 C 0.9019(4) 0.2500 0.0613(3) 0.0504(12) Uani 1 2 d S . . C52 C 0.9319(6) 0.2500 -0.0108(3) 0.0727(19) Uani 1 2 d S . . H52A H 1.008(6) 0.2500 -0.019(4) 0.109 Uiso 1 2 d S . . H52B H 0.907(4) 0.312(5) -0.035(3) 0.109 Uiso 1 1 d . . . C54 C 0.4034(4) 0.7500 0.4395(3) 0.0485(12) Uani 1 2 d S . . C55 C 0.4346(5) 0.7500 0.5130(3) 0.074(2) Uani 1 2 d S . . H55A H 0.505(7) 0.7500 0.513(4) 0.111 Uiso 1 2 d S . . H55B H 0.400(4) 0.678(5) 0.540(3) 0.111 Uiso 1 1 d . . . B1 B 0.2785(4) 0.2500 0.1014(2) 0.0305(10) Uani 1 2 d S . . B1B B 0.7731(4) 0.7500 0.3968(2) 0.0287(10) Uani 1 2 d S . . N25 N 0.5736(3) 0.2500 -0.13565(18) 0.0345(8) Uani 1 2 d S . . N25B N 1.0800(3) 0.7500 0.63454(18) 0.0345(8) Uani 1 2 d S . . C28 C 0.4390(3) 0.2500 -0.2045(2) 0.0422(11) Uani 1 2 d S . . H28 H 0.3959 0.2500 -0.2450 0.051 Uiso 1 2 calc SR . . C28B C 0.9463(4) 0.7500 0.7021(3) 0.0473(12) Uani 1 2 d S . . H28B H 0.9032 0.7500 0.7416 0.057 Uiso 1 2 calc SR . . N50 N 0.8791(4) 0.2500 0.1182(3) 0.0760(15) Uani 1 2 d S . . N53 N 0.3804(4) 0.7500 0.3829(3) 0.0711(14) Uani 1 2 d S . . 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 C1 0.062(2) 0.0200(14) 0.0240(13) 0.0037(11) 0.0034(12) -0.0068(14) C1B 0.0492(17) 0.0229(14) 0.0234(13) 0.0033(11) -0.0006(11) 0.0041(13) C2 0.065(2) 0.0324(16) 0.0367(16) -0.0002(13) 0.0141(14) 0.0067(16) C2B 0.076(2) 0.0276(15) 0.0287(15) 0.0006(12) 0.0083(14) 0.0024(16) C3 0.119(4) 0.040(2) 0.045(2) 0.0074(17) 0.030(2) 0.027(2) C3B 0.109(3) 0.0343(18) 0.0233(14) -0.0062(14) 0.0047(17) 0.007(2) C4 0.199(6) 0.0272(19) 0.036(2) 0.0051(16) 0.024(3) 0.028(3) C4B 0.108(3) 0.0254(16) 0.0380(18) 0.0020(14) -0.0132(19) -0.0135(19) C5 0.196(6) 0.0265(19) 0.0209(16) 0.0001(14) -0.008(2) -0.022(3) C5B 0.067(2) 0.0366(18) 0.0429(18) 0.0041(15) -0.0124(16) -0.0163(17) C6 0.103(3) 0.0280(16) 0.0285(15) 0.0028(13) -0.0077(16) -0.0132(18) C6B 0.0525(19) 0.0283(15) 0.0319(15) 0.0022(12) -0.0042(13) -0.0014(14) C7 0.045(3) 0.075(4) 0.023(2) 0.000 -0.0026(18) 0.000 C7B 0.044(2) 0.046(3) 0.0223(19) 0.000 0.0102(17) 0.000 C8 0.060(2) 0.122(4) 0.0343(18) -0.003(2) -0.0008(16) -0.040(3) C8B 0.048(2) 0.066(2) 0.0417(18) -0.0068(17) 0.0034(14) 0.0164(18) C9 0.071(4) 0.280(10) 0.039(2) -0.013(4) -0.002(3) -0.087(5) C9B 0.048(2) 0.126(4) 0.049(2) -0.011(3) 0.0042(17) 0.032(3) C10 0.049(5) 0.44(3) 0.028(3) 0.000 0.000(3) 0.000 C10B 0.028(3) 0.191(9) 0.038(3) 0.000 0.004(2) 0.000 C13 0.035(2) 0.0231(19) 0.0261(19) 0.000 0.0039(16) 0.000 C13B 0.034(2) 0.0241(19) 0.0260(19) 0.000 0.0010(16) 0.000 C14 0.0489(17) 0.0273(15) 0.0299(14) 0.0014(12) 0.0041(12) 0.0012(13) C14B 0.0449(17) 0.0260(15) 0.0291(14) 0.0008(12) -0.0016(12) 0.0002(13) C15 0.059(2) 0.0435(19) 0.0307(15) 0.0105(14) 0.0017(14) 0.0079(16) C15B 0.0557(19) 0.0374(18) 0.0290(14) 0.0094(13) -0.0006(13) -0.0083(15) C16 0.054(3) 0.062(3) 0.025(2) 0.000 -0.0017(19) 0.000 C16B 0.053(3) 0.056(3) 0.023(2) 0.000 0.0055(19) 0.000 C29 0.063(3) 0.053(3) 0.031(2) 0.000 -0.002(2) 0.000 C29B 0.062(3) 0.051(3) 0.033(2) 0.000 0.002(2) 0.000 N27 0.045(3) 0.110(5) 0.074(3) 0.000 0.006(2) 0.000 N27B 0.046(3) 0.069(3) 0.068(3) 0.000 -0.002(2) 0.000 C26 0.040(3) 0.135(6) 0.046(3) 0.000 0.006(2) 0.000 C26B 0.045(3) 0.069(4) 0.047(3) 0.000 -0.004(2) 0.000 C30 0.037(3) 0.043(3) 0.041(3) 0.000 0.004(2) 0.000 C30B 0.047(3) 0.035(2) 0.041(3) 0.000 0.002(2) 0.000 C51 0.034(3) 0.062(3) 0.056(3) 0.000 0.004(2) 0.000 C52 0.061(4) 0.102(6) 0.055(4) 0.000 0.002(3) 0.000 C54 0.034(2) 0.053(3) 0.058(3) 0.000 0.001(2) 0.000 C55 0.051(3) 0.120(6) 0.052(3) 0.000 0.000(3) 0.000 B1 0.039(3) 0.025(2) 0.027(2) 0.000 -0.0007(19) 0.000 B1B 0.041(3) 0.023(2) 0.023(2) 0.000 0.0073(18) 0.000 N25 0.0366(19) 0.0292(18) 0.0378(19) 0.000 -0.0004(15) 0.000 N25B 0.041(2) 0.0230(17) 0.0394(19) 0.000 0.0013(16) 0.000 C28 0.041(3) 0.035(2) 0.049(3) 0.000 -0.018(2) 0.000 C28B 0.056(3) 0.037(3) 0.050(3) 0.000 0.018(2) 0.000 N50 0.057(3) 0.107(5) 0.064(3) 0.000 0.007(2) 0.000 N53 0.059(3) 0.096(4) 0.058(3) 0.000 -0.008(2) 0.000 _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 C1 C2 1.399(5) . ? C1 C6 1.401(4) . ? C1 B1 1.648(4) . ? C1B C6B 1.395(4) . ? C1B C2B 1.398(4) . ? C1B B1B 1.646(4) . ? C2 C3 1.394(5) . ? C2B C3B 1.402(5) . ? C3 C4 1.355(7) . ? C3B C4B 1.374(5) . ? C4 C5 1.361(7) . ? C4B C5B 1.366(5) . ? C5 C6 1.414(6) . ? C5B C6B 1.388(4) . ? C7 C8 1.404(5) . ? C7 C8 1.404(5) 4_565 ? C7 B1 1.622(7) . ? C7B C8B 1.401(4) . ? C7B C8B 1.401(4) 4_575 ? C7B B1B 1.632(6) . ? C8 C9 1.387(6) . ? C8B C9B 1.374(5) . ? C9 C10 1.370(8) . ? C9B C10B 1.375(6) . ? C10 C9 1.370(8) 4_565 ? C10B C9B 1.375(6) 4_575 ? C13 C14 1.400(3) 4_565 ? C13 C14 1.400(3) . ? C13 B1 1.643(6) . ? C13B C14B 1.404(3) 4_575 ? C13B C14B 1.404(3) . ? C13B B1B 1.640(5) . ? C14 C15 1.389(4) . ? C14B C15B 1.383(4) . ? C15 C16 1.378(4) . ? C15B C16B 1.380(4) . ? C16 C15 1.378(4) 4_565 ? C16B C15B 1.380(4) 4_575 ? C29 C28 1.306(7) . ? C29 N25 1.350(6) . ? C29B C28B 1.317(7) . ? C29B N25B 1.380(6) . ? N27 C26 1.314(7) . ? N27 C28 1.375(7) . ? N27B C26B 1.312(7) . ? N27B C28B 1.375(7) . ? C26 N25 1.319(6) . ? C26B N25B 1.316(6) . ? C30 N25 1.466(6) . ? C30B N25B 1.462(6) . ? C51 N50 1.134(7) . ? C51 C52 1.441(8) . ? C54 N53 1.119(6) . ? C54 C55 1.456(8) . ? B1 C1 1.648(4) 4_565 ? B1B C1B 1.646(4) 4_575 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 115.0(3) . . ? C2 C1 B1 122.1(3) . . ? C6 C1 B1 122.2(3) . . ? C6B C1B C2B 115.1(3) . . ? C6B C1B B1B 121.9(3) . . ? C2B C1B B1B 122.2(3) . . ? C3 C2 C1 123.5(3) . . ? C1B C2B C3B 121.7(3) . . ? C4 C3 C2 120.2(4) . . ? C4B C3B C2B 120.9(3) . . ? C3 C4 C5 118.9(4) . . ? C5B C4B C3B 118.7(3) . . ? C4 C5 C6 121.7(4) . . ? C4B C5B C6B 120.4(3) . . ? C1 C6 C5 120.7(4) . . ? C5B C6B C1B 123.2(3) . . ? C8 C7 C8 115.5(5) . 4_565 ? C8 C7 B1 122.1(3) . . ? C8 C7 B1 122.1(3) 4_565 . ? C8B C7B C8B 115.2(4) . 4_575 ? C8B C7B B1B 122.3(2) . . ? C8B C7B B1B 122.3(2) 4_575 . ? C9 C8 C7 121.5(6) . . ? C9B C8B C7B 122.1(4) . . ? C10 C9 C8 121.9(8) . . ? C8B C9B C10B 121.4(5) . . ? C9 C10 C9 117.6(8) 4_565 . ? C9B C10B C9B 117.7(5) . 4_575 ? C14 C13 C14 115.0(3) 4_565 . ? C14 C13 B1 122.42(18) 4_565 . ? C14 C13 B1 122.42(18) . . ? C14B C13B C14B 114.6(3) 4_575 . ? C14B C13B B1B 122.65(17) 4_575 . ? C14B C13B B1B 122.66(17) . . ? C15 C14 C13 122.7(3) . . ? C15B C14B C13B 123.0(3) . . ? C16 C15 C14 120.3(3) . . ? C16B C15B C14B 120.3(3) . . ? C15 C16 C15 118.8(4) . 4_565 ? C15B C16B C15B 118.9(4) . 4_575 ? C28 C29 N25 109.9(4) . . ? C28B C29B N25B 108.6(4) . . ? C26 N27 C28 107.5(4) . . ? C26B N27B C28B 108.8(4) . . ? N27 C26 N25 109.7(5) . . ? N27B C26B N25B 109.2(5) . . ? N50 C51 C52 179.5(6) . . ? N53 C54 C55 179.3(6) . . ? C7 B1 C13 105.7(3) . . ? C7 B1 C1 113.6(2) . 4_565 ? C13 B1 C1 111.5(2) . 4_565 ? C7 B1 C1 113.6(2) . . ? C13 B1 C1 111.5(2) . . ? C1 B1 C1 101.1(3) 4_565 . ? C7B B1B C13B 104.9(3) . . ? C7B B1B C1B 113.4(2) . . ? C13B B1B C1B 111.8(2) . . ? C7B B1B C1B 113.4(2) . 4_575 ? C13B B1B C1B 111.8(2) . 4_575 ? C1B B1B C1B 101.8(3) . 4_575 ? C26 N25 C29 106.5(4) . . ? C26 N25 C30 126.2(4) . . ? C29 N25 C30 127.2(4) . . ? C26B N25B C29B 107.1(4) . . ? C26B N25B C30B 126.2(4) . . ? C29B N25B C30B 126.7(4) . . ? C29 C28 N27 106.4(4) . . ? C29B C28B N27B 106.2(4) . . ? 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 C6 C1 C2 C3 0.3(4) . . . . ? B1 C1 C2 C3 170.5(3) . . . . ? C6B C1B C2B C3B 0.5(4) . . . . ? B1B C1B C2B C3B -169.7(3) . . . . ? C1 C2 C3 C4 -0.9(5) . . . . ? C1B C2B C3B C4B 0.1(5) . . . . ? C2 C3 C4 C5 0.9(6) . . . . ? C2B C3B C4B C5B -0.6(5) . . . . ? C3 C4 C5 C6 -0.4(6) . . . . ? C3B C4B C5B C6B 0.4(5) . . . . ? C2 C1 C6 C5 0.3(4) . . . . ? B1 C1 C6 C5 -169.9(3) . . . . ? C4 C5 C6 C1 -0.2(5) . . . . ? C4B C5B C6B C1B 0.2(5) . . . . ? C2B C1B C6B C5B -0.7(4) . . . . ? B1B C1B C6B C5B 169.6(3) . . . . ? C8 C7 C8 C9 -3.5(6) 4_565 . . . ? B1 C7 C8 C9 -178.7(4) . . . . ? C8B C7B C8B C9B -2.2(6) 4_575 . . . ? B1B C7B C8B C9B -177.7(3) . . . . ? C7 C8 C9 C10 1.9(8) . . . . ? C7B C8B C9B C10B 0.3(6) . . . . ? C8 C9 C10 C9 0.0(12) . . . 4_565 ? C8B C9B C10B C9B 1.7(8) . . . 4_575 ? C14 C13 C14 C15 2.5(6) 4_565 . . . ? B1 C13 C14 C15 178.1(3) . . . . ? C14B C13B C14B C15B 1.9(6) 4_575 . . . ? B1B C13B C14B C15B 178.0(3) . . . . ? C13 C14 C15 C16 -0.6(5) . . . . ? C13B C14B C15B C16B -0.4(5) . . . . ? C14 C15 C16 C15 -1.5(7) . . . 4_565 ? C14B C15B C16B C15B -1.3(7) . . . 4_575 ? C28 N27 C26 N25 0.0 . . . . ? C28B N27B C26B N25B 0.000(1) . . . . ? C8 C7 B1 C13 87.4(3) . . . . ? C8 C7 B1 C13 -87.4(3) 4_565 . . . ? C8 C7 B1 C1 -150.0(3) . . . 4_565 ? C8 C7 B1 C1 35.2(5) 4_565 . . 4_565 ? C8 C7 B1 C1 -35.2(5) . . . . ? C8 C7 B1 C1 150.0(3) 4_565 . . . ? C14 C13 B1 C7 87.6(3) 4_565 . . . ? C14 C13 B1 C7 -87.6(3) . . . . ? C14 C13 B1 C1 -36.3(5) 4_565 . . 4_565 ? C14 C13 B1 C1 148.5(3) . . . 4_565 ? C14 C13 B1 C1 -148.5(3) 4_565 . . . ? C14 C13 B1 C1 36.3(5) . . . . ? C2 C1 B1 C7 154.4(3) . . . . ? C6 C1 B1 C7 -36.1(4) . . . . ? C2 C1 B1 C13 35.1(4) . . . . ? C6 C1 B1 C13 -155.4(3) . . . . ? C2 C1 B1 C1 -83.5(3) . . . 4_565 ? C6 C1 B1 C1 86.0(4) . . . 4_565 ? C8B C7B B1B C13B 87.6(3) . . . . ? C8B C7B B1B C13B -87.6(3) 4_575 . . . ? C8B C7B B1B C1B -34.7(5) . . . . ? C8B C7B B1B C1B 150.2(3) 4_575 . . . ? C8B C7B B1B C1B -150.2(3) . . . 4_575 ? C8B C7B B1B C1B 34.7(5) 4_575 . . 4_575 ? C14B C13B B1B C7B 87.9(3) 4_575 . . . ? C14B C13B B1B C7B -87.9(3) . . . . ? C14B C13B B1B C1B -148.8(3) 4_575 . . . ? C14B C13B B1B C1B 35.4(5) . . . . ? C14B C13B B1B C1B -35.4(5) 4_575 . . 4_575 ? C14B C13B B1B C1B 148.8(3) . . . 4_575 ? C6B C1B B1B C7B 153.5(3) . . . . ? C2B C1B B1B C7B -36.9(4) . . . . ? C6B C1B B1B C13B 35.2(4) . . . . ? C2B C1B B1B C13B -155.2(3) . . . . ? C6B C1B B1B C1B -84.3(3) . . . 4_575 ? C2B C1B B1B C1B 85.3(4) . . . 4_575 ? N27 C26 N25 C29 0.0 . . . . ? N27 C26 N25 C30 180.0 . . . . ? C28 C29 N25 C26 0.0 . . . . ? C28 C29 N25 C30 180.0 . . . . ? N27B C26B N25B C29B 0.000(1) . . . . ? N27B C26B N25B C30B 180.000(1) . . . . ? C28B C29B N25B C26B 0.000(1) . . . . ? C28B C29B N25B C30B 180.000(1) . . . . ? N25 C29 C28 N27 0.0 . . . . ? C26 N27 C28 C29 0.0 . . . . ? N25B C29B C28B N27B 0.000(1) . . . . ? C26B N27B C28B C29B 0.000(1) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.433 _refine_diff_density_min -0.465 _refine_diff_density_rms 0.054 #===END data_comp4 _database_code_CSD 156978 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H35 B N2 O2' _chemical_formula_weight 526.46 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' '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 P21/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 11.2280(6) _cell_length_b 16.220(1) _cell_length_c 16.2719(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.991(3) _cell_angle_gamma 90.00 _cell_volume 2927.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173.0(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min 0.9749 _exptl_absorpt_correction_T_max 0.9855 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(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 14479 _diffrn_reflns_av_R_equivalents 0.0583 _diffrn_reflns_av_sigmaI/netI 0.0777 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5122 _reflns_number_gt 3261 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.1075P)^2^+3.0787P] 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 5122 _refine_ls_number_parameters 377 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1344 _refine_ls_R_factor_gt 0.0823 _refine_ls_wR_factor_ref 0.2342 _refine_ls_wR_factor_gt 0.2035 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.042 _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 C1 C 0.5134(3) 0.2122(2) 0.1719(2) 0.0302(8) Uani 1 1 d . . . C2 C 0.5946(3) 0.2291(2) 0.2435(2) 0.0404(9) Uani 1 1 d . . . H2 H 0.6476 0.2747 0.2430 0.049 Uiso 1 1 calc R . . C3 C 0.6020(4) 0.1826(3) 0.3155(2) 0.0542(11) Uani 1 1 d . . . H3 H 0.6594 0.1964 0.3628 0.065 Uiso 1 1 calc R . . C4 C 0.5257(4) 0.1164(3) 0.3185(3) 0.0583(12) Uani 1 1 d . . . H4 H 0.5311 0.0836 0.3673 0.070 Uiso 1 1 calc R . . C5 C 0.4414(4) 0.0982(3) 0.2495(2) 0.0512(11) Uani 1 1 d . . . H5 H 0.3872 0.0534 0.2509 0.061 Uiso 1 1 calc R . . C6 C 0.4366(3) 0.1456(2) 0.1786(2) 0.0385(9) Uani 1 1 d . . . H6 H 0.3779 0.1322 0.1319 0.046 Uiso 1 1 calc R . . C7 C 0.3740(3) 0.3247(2) 0.09434(19) 0.0268(7) Uani 1 1 d . . . C8 C 0.3803(3) 0.3880(2) 0.1543(2) 0.0332(8) Uani 1 1 d . . . H8 H 0.4560 0.4000 0.1871 0.040 Uiso 1 1 calc R . . C9 C 0.2798(3) 0.4336(2) 0.1671(2) 0.0383(9) Uani 1 1 d . . . H9 H 0.2878 0.4753 0.2086 0.046 Uiso 1 1 calc R . . C10 C 0.1685(3) 0.4185(2) 0.1200(2) 0.0401(9) Uani 1 1 d . . . H10 H 0.1001 0.4500 0.1283 0.048 Uiso 1 1 calc R . . C11 C 0.1584(3) 0.3569(2) 0.0607(2) 0.0375(9) Uani 1 1 d . . . H11 H 0.0826 0.3460 0.0276 0.045 Uiso 1 1 calc R . . C12 C 0.2597(3) 0.3105(2) 0.0494(2) 0.0300(8) Uani 1 1 d . . . H12 H 0.2501 0.2674 0.0093 0.036 Uiso 1 1 calc R . . C13 C 0.6119(3) 0.3292(2) 0.08084(19) 0.0281(8) Uani 1 1 d . . . C14 C 0.7301(3) 0.2990(2) 0.0997(2) 0.0423(10) Uani 1 1 d . . . H14 H 0.7426 0.2444 0.1203 0.051 Uiso 1 1 calc R . . C15 C 0.8298(3) 0.3468(3) 0.0892(2) 0.0475(11) Uani 1 1 d . . . H15 H 0.9086 0.3246 0.1040 0.057 Uiso 1 1 calc R . . C16 C 0.8159(3) 0.4254(2) 0.0578(2) 0.0401(9) Uani 1 1 d . . . H16 H 0.8840 0.4573 0.0495 0.048 Uiso 1 1 calc R . . C17 C 0.7008(3) 0.4572(2) 0.0387(2) 0.0349(8) Uani 1 1 d . . . H17 H 0.6892 0.5115 0.0171 0.042 Uiso 1 1 calc R . . C18 C 0.6020(3) 0.4101(2) 0.05097(19) 0.0278(8) Uani 1 1 d . . . H18 H 0.5240 0.4339 0.0385 0.033 Uiso 1 1 calc R . . C19 C 0.4806(3) 0.2122(2) 0.0024(2) 0.0292(8) Uani 1 1 d . . . C20 C 0.4264(3) 0.2414(2) -0.0753(2) 0.0305(8) Uani 1 1 d . . . H20 H 0.3918 0.2950 -0.0783 0.037 Uiso 1 1 calc R . . C21 C 0.4204(3) 0.1962(2) -0.1483(2) 0.0392(9) Uani 1 1 d . . . H21 H 0.3809 0.2185 -0.1993 0.047 Uiso 1 1 calc R . . C22 C 0.4715(4) 0.1194(3) -0.1467(3) 0.0567(12) Uani 1 1 d . . . H22 H 0.4685 0.0879 -0.1961 0.068 Uiso 1 1 calc R . . C23 C 0.5277(6) 0.0891(3) -0.0709(3) 0.0796(17) Uani 1 1 d . . . H23 H 0.5643 0.0362 -0.0687 0.096 Uiso 1 1 calc R . . C24 C 0.5318(5) 0.1338(3) 0.0010(2) 0.0604(13) Uani 1 1 d . . . H24 H 0.5708 0.1106 0.0518 0.073 Uiso 1 1 calc R . . C26 C 0.3198(4) 0.6762(3) 0.1328(3) 0.0537(12) Uani 1 1 d . . . H26 H 0.2865 0.6712 0.0756 0.064 Uiso 1 1 calc R . . C27 C 0.4156(4) 0.6278(3) 0.1654(2) 0.0460(10) Uani 1 1 d . . . H27 H 0.4478 0.5887 0.1314 0.055 Uiso 1 1 calc R . . C28 C 0.4646(4) 0.6361(2) 0.2478(2) 0.0432(10) Uani 1 1 d . . . C29 C 0.4119(4) 0.6907(3) 0.2966(2) 0.0482(10) Uani 1 1 d . . . H29 H 0.4426 0.6960 0.3541 0.058 Uiso 1 1 calc R . . C30 C 0.3159(4) 0.7368(3) 0.2617(2) 0.0521(11) Uani 1 1 d . . . H30 H 0.2793 0.7739 0.2954 0.063 Uiso 1 1 calc R . . C31 C 0.1718(5) 0.7854(5) 0.1465(3) 0.0853(19) Uani 1 1 d . . . H31A H 0.1009 0.7668 0.1708 0.102 Uiso 0.559(13) 1 calc PR A 1 H31B H 0.1927 0.8409 0.1695 0.102 Uiso 0.559(13) 1 calc PR A 1 H31C H 0.1100 0.7535 0.1095 0.102 Uiso 0.441(13) 1 calc PR A 2 H31D H 0.1337 0.8084 0.1924 0.102 Uiso 0.441(13) 1 calc PR A 2 C32 C 0.1303(8) 0.7966(6) 0.0575(5) 0.057(3) Uani 0.559(13) 1 d P A 1 H32A H 0.1762 0.8412 0.0365 0.086 Uiso 0.559(13) 1 calc PR A 1 H32B H 0.0444 0.8107 0.0483 0.086 Uiso 0.559(13) 1 calc PR A 1 H32C H 0.1426 0.7454 0.0279 0.086 Uiso 0.559(13) 1 calc PR A 1 C32B C 0.2102(14) 0.8429(10) 0.1063(10) 0.091(6) Uani 0.441(13) 1 d P A 2 H32D H 0.1429 0.8785 0.0829 0.137 Uiso 0.441(13) 1 calc PR A 2 H32E H 0.2483 0.8199 0.0611 0.137 Uiso 0.441(13) 1 calc PR A 2 H32F H 0.2696 0.8753 0.1434 0.137 Uiso 0.441(13) 1 calc PR A 2 C33 C 0.5761(4) 0.5904(3) 0.2861(3) 0.0508(11) Uani 1 1 d . . . C35 C 0.7245(5) 0.4952(4) 0.2613(3) 0.0780(16) Uani 1 1 d . . . H35A H 0.7876 0.5336 0.2858 0.117 Uiso 1 1 calc R . . H35B H 0.7510 0.4662 0.2145 0.117 Uiso 1 1 calc R . . H35C H 0.7089 0.4551 0.3034 0.117 Uiso 1 1 calc R . . B1 B 0.4954(3) 0.2697(2) 0.0872(2) 0.0267(8) Uani 1 1 d . . . N25 N 0.2725(3) 0.7305(2) 0.1808(2) 0.0534(10) Uani 1 1 d . A . O33 O 0.6252(3) 0.6010(2) 0.35677(19) 0.0746(10) Uani 1 1 d . . . O34 O 0.6149(3) 0.5407(2) 0.23192(17) 0.0624(9) Uani 1 1 d . . . C52 C 0.6954(10) 0.4385(7) 0.4760(4) 0.099(4) Uani 0.744(13) 1 d PD B 1 H52A H 0.7488 0.4807 0.4587 0.149 Uiso 0.744(13) 1 calc PR B 1 H52B H 0.6250 0.4316 0.4328 0.149 Uiso 0.744(13) 1 calc PR B 1 H52C H 0.7390 0.3861 0.4847 0.149 Uiso 0.744(13) 1 calc PR B 1 C52B C 0.633(3) 0.3970(12) 0.4845(11) 0.099(4) Uani 0.256(13) 1 d PD B 2 H52D H 0.6183 0.4237 0.4299 0.149 Uiso 0.256(13) 1 calc PR B 2 H52E H 0.5634 0.3636 0.4924 0.149 Uiso 0.256(13) 1 calc PR B 2 H52F H 0.7047 0.3615 0.4878 0.149 Uiso 0.256(13) 1 calc PR B 2 C51 C 0.6558(6) 0.4641(4) 0.5539(5) 0.106(2) Uani 1 1 d D . . N50 N 0.6296(8) 0.4867(5) 0.6186(5) 0.152(3) Uani 1 1 d . B . 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 C1 0.0292(17) 0.034(2) 0.0292(18) 0.0044(14) 0.0094(15) 0.0019(15) C2 0.0332(19) 0.050(2) 0.037(2) 0.0129(17) 0.0012(16) -0.0065(17) C3 0.050(2) 0.072(3) 0.036(2) 0.017(2) -0.0053(18) -0.008(2) C4 0.071(3) 0.064(3) 0.039(2) 0.027(2) 0.009(2) -0.008(2) C5 0.062(3) 0.050(3) 0.043(2) 0.0157(19) 0.009(2) -0.018(2) C6 0.045(2) 0.040(2) 0.0303(19) 0.0057(16) 0.0037(16) -0.0100(18) C7 0.0285(17) 0.0277(18) 0.0259(16) 0.0040(14) 0.0093(14) -0.0052(14) C8 0.0277(18) 0.039(2) 0.0339(18) -0.0018(15) 0.0089(15) -0.0064(15) C9 0.038(2) 0.039(2) 0.042(2) -0.0069(17) 0.0184(18) -0.0022(16) C10 0.032(2) 0.043(2) 0.049(2) 0.0008(18) 0.0194(18) 0.0066(17) C11 0.0227(17) 0.050(2) 0.041(2) 0.0067(18) 0.0082(15) -0.0010(16) C12 0.0279(17) 0.033(2) 0.0299(17) 0.0010(14) 0.0087(14) -0.0049(15) C13 0.0257(17) 0.035(2) 0.0243(16) 0.0028(14) 0.0054(13) 0.0006(14) C14 0.0293(19) 0.047(2) 0.052(2) 0.0221(19) 0.0116(17) 0.0080(17) C15 0.0211(18) 0.071(3) 0.051(2) 0.016(2) 0.0078(17) 0.0059(18) C16 0.0283(19) 0.055(3) 0.038(2) 0.0052(18) 0.0077(16) -0.0130(18) C17 0.037(2) 0.035(2) 0.0337(19) 0.0016(16) 0.0087(16) -0.0067(16) C18 0.0250(17) 0.0309(19) 0.0283(17) -0.0001(14) 0.0066(14) 0.0008(14) C19 0.0300(18) 0.0287(19) 0.0311(18) 0.0015(14) 0.0115(15) 0.0013(15) C20 0.0266(17) 0.0327(19) 0.0324(18) -0.0006(15) 0.0054(15) -0.0016(15) C21 0.035(2) 0.049(2) 0.033(2) -0.0023(17) 0.0064(16) -0.0098(18) C22 0.076(3) 0.049(3) 0.050(3) -0.018(2) 0.025(2) -0.004(2) C23 0.144(5) 0.040(3) 0.059(3) -0.004(2) 0.030(3) 0.039(3) C24 0.099(4) 0.047(3) 0.037(2) 0.0068(19) 0.018(2) 0.032(3) C26 0.039(2) 0.086(3) 0.038(2) -0.014(2) 0.0104(19) -0.013(2) C27 0.051(2) 0.052(3) 0.038(2) -0.0137(18) 0.0160(19) -0.015(2) C28 0.052(2) 0.043(2) 0.037(2) -0.0054(17) 0.0151(18) -0.0096(19) C29 0.061(3) 0.053(3) 0.031(2) -0.0081(18) 0.0112(19) -0.003(2) C30 0.056(3) 0.068(3) 0.035(2) -0.009(2) 0.016(2) 0.002(2) C31 0.051(3) 0.156(6) 0.050(3) 0.014(3) 0.015(2) 0.022(3) C32 0.052(5) 0.068(6) 0.051(5) -0.014(4) 0.005(4) 0.021(5) C32B 0.078(10) 0.093(11) 0.109(12) 0.033(10) 0.033(9) 0.031(9) C33 0.065(3) 0.046(3) 0.042(2) -0.0085(19) 0.011(2) -0.001(2) C35 0.080(4) 0.091(4) 0.062(3) -0.006(3) 0.012(3) 0.035(3) B1 0.0244(18) 0.030(2) 0.0259(19) 0.0023(16) 0.0045(15) -0.0006(16) N25 0.0419(19) 0.085(3) 0.0357(18) -0.0078(18) 0.0146(16) -0.0047(18) O33 0.090(3) 0.079(3) 0.050(2) -0.0158(17) -0.0032(18) 0.0201(19) O34 0.070(2) 0.070(2) 0.0474(17) -0.0127(15) 0.0117(15) 0.0154(17) C52 0.148(9) 0.113(8) 0.049(4) 0.046(4) 0.054(4) 0.077(7) C52B 0.148(9) 0.113(8) 0.049(4) 0.046(4) 0.054(4) 0.077(7) C51 0.099(5) 0.076(5) 0.134(6) 0.030(4) -0.011(5) -0.009(4) N50 0.184(8) 0.149(7) 0.130(6) -0.004(5) 0.048(6) -0.016(5) _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 C1 C2 1.390(5) . ? C1 C6 1.397(5) . ? C1 B1 1.651(5) . ? C2 C3 1.384(5) . ? C3 C4 1.380(6) . ? C4 C5 1.382(6) . ? C5 C6 1.380(5) . ? C7 C12 1.394(5) . ? C7 C8 1.410(5) . ? C7 B1 1.648(5) . ? C8 C9 1.392(5) . ? C9 C10 1.382(5) . ? C10 C11 1.381(5) . ? C11 C12 1.400(5) . ? C13 C18 1.397(5) . ? C13 C14 1.402(5) . ? C13 B1 1.642(5) . ? C14 C15 1.393(5) . ? C15 C16 1.374(6) . ? C16 C17 1.381(5) . ? C17 C18 1.387(5) . ? C19 C24 1.397(5) . ? C19 C20 1.397(5) . ? C19 B1 1.652(5) . ? C20 C21 1.389(5) . ? C21 C22 1.369(6) . ? C22 C23 1.384(7) . ? C23 C24 1.372(6) . ? C26 N25 1.341(5) . ? C26 C27 1.370(6) . ? C27 C28 1.374(5) . ? C28 C29 1.383(5) . ? C28 C33 1.503(6) . ? C29 C30 1.360(6) . ? C30 N25 1.334(5) . ? C31 C32B 1.255(14) . ? C31 C32 1.461(9) . ? C31 N25 1.478(6) . ? C33 O33 1.207(5) . ? C33 O34 1.318(5) . ? C35 O34 1.450(5) . ? C52 C51 1.467(8) . ? C52B C51 1.560(10) . ? C51 N50 1.193(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 114.8(3) . . ? C2 C1 B1 124.5(3) . . ? C6 C1 B1 120.4(3) . . ? C3 C2 C1 123.1(4) . . ? C4 C3 C2 119.9(4) . . ? C3 C4 C5 119.2(3) . . ? C6 C5 C4 119.5(4) . . ? C5 C6 C1 123.5(3) . . ? C12 C7 C8 115.2(3) . . ? C12 C7 B1 125.2(3) . . ? C8 C7 B1 119.4(3) . . ? C9 C8 C7 122.4(3) . . ? C10 C9 C8 120.5(3) . . ? C11 C10 C9 118.9(3) . . ? C10 C11 C12 120.1(3) . . ? C7 C12 C11 122.8(3) . . ? C18 C13 C14 115.1(3) . . ? C18 C13 B1 123.5(3) . . ? C14 C13 B1 121.2(3) . . ? C15 C14 C13 122.0(3) . . ? C16 C15 C14 121.0(3) . . ? C15 C16 C17 118.6(3) . . ? C16 C17 C18 120.2(3) . . ? C17 C18 C13 123.0(3) . . ? C24 C19 C20 114.6(3) . . ? C24 C19 B1 122.6(3) . . ? C20 C19 B1 122.5(3) . . ? C21 C20 C19 123.4(3) . . ? C22 C21 C20 120.0(4) . . ? C21 C22 C23 118.1(4) . . ? C24 C23 C22 121.5(4) . . ? C23 C24 C19 122.4(4) . . ? N25 C26 C27 120.6(4) . . ? C26 C27 C28 119.5(4) . . ? C27 C28 C29 118.7(4) . . ? C27 C28 C33 122.5(4) . . ? C29 C28 C33 118.8(3) . . ? C30 C29 C28 119.7(4) . . ? N25 C30 C29 120.9(4) . . ? C32B C31 C32 58.2(9) . . ? C32B C31 N25 109.8(7) . . ? C32 C31 N25 123.8(5) . . ? O33 C33 O34 125.1(4) . . ? O33 C33 C28 123.5(4) . . ? O34 C33 C28 111.4(4) . . ? C13 B1 C7 111.2(3) . . ? C13 B1 C1 112.9(3) . . ? C7 B1 C1 104.0(2) . . ? C13 B1 C19 104.8(2) . . ? C7 B1 C19 112.9(3) . . ? C1 B1 C19 111.2(3) . . ? C30 N25 C26 120.5(4) . . ? C30 N25 C31 117.9(4) . . ? C26 N25 C31 121.6(4) . . ? C33 O34 C35 116.3(3) . . ? N50 C51 C52 176.5(10) . . ? N50 C51 C52B 144.9(14) . . ? C52 C51 C52B 38.2(10) . . ? 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 C6 C1 C2 C3 1.7(5) . . . . ? B1 C1 C2 C3 175.6(4) . . . . ? C1 C2 C3 C4 -0.5(7) . . . . ? C2 C3 C4 C5 -1.1(7) . . . . ? C3 C4 C5 C6 1.2(7) . . . . ? C4 C5 C6 C1 0.1(6) . . . . ? C2 C1 C6 C5 -1.5(5) . . . . ? B1 C1 C6 C5 -175.7(4) . . . . ? C12 C7 C8 C9 -0.6(5) . . . . ? B1 C7 C8 C9 -176.1(3) . . . . ? C7 C8 C9 C10 -0.7(5) . . . . ? C8 C9 C10 C11 0.8(5) . . . . ? C9 C10 C11 C12 0.4(5) . . . . ? C8 C7 C12 C11 1.8(5) . . . . ? B1 C7 C12 C11 177.0(3) . . . . ? C10 C11 C12 C7 -1.8(5) . . . . ? C18 C13 C14 C15 0.0(5) . . . . ? B1 C13 C14 C15 175.5(3) . . . . ? C13 C14 C15 C16 -1.5(6) . . . . ? C14 C15 C16 C17 1.6(6) . . . . ? C15 C16 C17 C18 -0.2(5) . . . . ? C16 C17 C18 C13 -1.4(5) . . . . ? C14 C13 C18 C17 1.4(5) . . . . ? B1 C13 C18 C17 -173.9(3) . . . . ? C24 C19 C20 C21 1.5(5) . . . . ? B1 C19 C20 C21 175.4(3) . . . . ? C19 C20 C21 C22 -1.4(5) . . . . ? C20 C21 C22 C23 0.3(6) . . . . ? C21 C22 C23 C24 0.6(8) . . . . ? C22 C23 C24 C19 -0.4(9) . . . . ? C20 C19 C24 C23 -0.6(7) . . . . ? B1 C19 C24 C23 -174.5(4) . . . . ? N25 C26 C27 C28 -1.0(6) . . . . ? C26 C27 C28 C29 3.0(6) . . . . ? C26 C27 C28 C33 -174.6(4) . . . . ? C27 C28 C29 C30 -2.2(6) . . . . ? C33 C28 C29 C30 175.5(4) . . . . ? C28 C29 C30 N25 -0.6(6) . . . . ? C27 C28 C33 O33 174.9(4) . . . . ? C29 C28 C33 O33 -2.8(6) . . . . ? C27 C28 C33 O34 -2.6(6) . . . . ? C29 C28 C33 O34 179.7(4) . . . . ? C18 C13 B1 C7 -24.8(4) . . . . ? C14 C13 B1 C7 160.2(3) . . . . ? C18 C13 B1 C1 -141.2(3) . . . . ? C14 C13 B1 C1 43.7(4) . . . . ? C18 C13 B1 C19 97.5(3) . . . . ? C14 C13 B1 C19 -77.5(4) . . . . ? C12 C7 B1 C13 134.5(3) . . . . ? C8 C7 B1 C13 -50.5(4) . . . . ? C12 C7 B1 C1 -103.7(3) . . . . ? C8 C7 B1 C1 71.3(4) . . . . ? C12 C7 B1 C19 16.9(4) . . . . ? C8 C7 B1 C19 -168.1(3) . . . . ? C2 C1 B1 C13 20.8(4) . . . . ? C6 C1 B1 C13 -165.7(3) . . . . ? C2 C1 B1 C7 -99.9(4) . . . . ? C6 C1 B1 C7 73.6(4) . . . . ? C2 C1 B1 C19 138.3(3) . . . . ? C6 C1 B1 C19 -48.2(4) . . . . ? C24 C19 B1 C13 94.4(4) . . . . ? C20 C19 B1 C13 -79.1(4) . . . . ? C24 C19 B1 C7 -144.4(4) . . . . ? C20 C19 B1 C7 42.1(4) . . . . ? C24 C19 B1 C1 -28.0(4) . . . . ? C20 C19 B1 C1 158.6(3) . . . . ? C29 C30 N25 C26 2.7(6) . . . . ? C29 C30 N25 C31 -177.2(4) . . . . ? C27 C26 N25 C30 -1.9(6) . . . . ? C27 C26 N25 C31 178.0(4) . . . . ? C32B C31 N25 C30 103.7(10) . . . . ? C32 C31 N25 C30 168.1(7) . . . . ? C32B C31 N25 C26 -76.1(11) . . . . ? C32 C31 N25 C26 -11.8(9) . . . . ? O33 C33 O34 C35 0.6(7) . . . . ? C28 C33 O34 C35 178.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.601 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.058 #===END data_comp7 _database_code_CSD 156979 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H23 B N2' _chemical_formula_weight 386.28 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' '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'C2/c' 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' '-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 27.494(1) _cell_length_b 9.4662(6) _cell_length_c 20.009(1) _cell_angle_alpha 90.00 _cell_angle_beta 127.67(3) _cell_angle_gamma 90.00 _cell_volume 4121.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173.0(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9822 _exptl_absorpt_correction_T_max 0.9858 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(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 10097 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0741 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3632 _reflns_number_gt 2349 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0439P)^2^+1.0845P] 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 SHELXL _refine_ls_extinction_coef 0.0037(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3632 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0957 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1119 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 C1 C 0.20451(9) 1.1497(2) 0.15873(13) 0.0280(5) Uani 1 1 d . . . C2 C 0.23254(9) 1.2446(2) 0.13820(14) 0.0313(5) Uani 1 1 d . . . H2 H 0.2078 1.2965 0.0870 0.038 Uiso 1 1 calc R . . C3 C 0.29583(10) 1.2646(2) 0.19106(15) 0.0383(6) Uani 1 1 d . . . H3 H 0.3136 1.3294 0.1754 0.046 Uiso 1 1 calc R . . C4 C 0.33313(10) 1.1912(2) 0.26625(14) 0.0384(6) Uani 1 1 d . . . H4 H 0.3764 1.2043 0.3018 0.046 Uiso 1 1 calc R . . C5 C 0.30662(9) 1.0984(2) 0.28903(14) 0.0360(5) Uani 1 1 d . . . H5 H 0.3316 1.0480 0.3408 0.043 Uiso 1 1 calc R . . C6 C 0.24350(9) 1.0794(2) 0.23595(13) 0.0337(5) Uani 1 1 d . . . H6 H 0.2260 1.0159 0.2527 0.040 Uiso 1 1 calc R . . C7 C 0.10673(8) 1.1264(2) 0.15502(13) 0.0299(5) Uani 1 1 d . . . C8 C 0.07532(9) 1.0260(2) 0.16651(13) 0.0359(5) Uani 1 1 d . . . H8 H 0.0665 0.9367 0.1396 0.043 Uiso 1 1 calc R . . C9 C 0.05642(10) 1.0520(3) 0.21597(15) 0.0471(6) Uani 1 1 d . . . H9 H 0.0353 0.9805 0.2224 0.056 Uiso 1 1 calc R . . C10 C 0.06794(10) 1.1799(3) 0.25548(15) 0.0502(7) Uani 1 1 d . . . H10 H 0.0548 1.1974 0.2890 0.060 Uiso 1 1 calc R . . C11 C 0.09886(10) 1.2828(3) 0.24580(15) 0.0458(6) Uani 1 1 d . . . H11 H 0.1069 1.3721 0.2724 0.055 Uiso 1 1 calc R . . C12 C 0.11812(10) 1.2555(2) 0.19736(14) 0.0383(6) Uani 1 1 d . . . H12 H 0.1400 1.3270 0.1924 0.046 Uiso 1 1 calc R . . C13 C 0.08919(8) 1.2050(2) 0.01159(13) 0.0284(5) Uani 1 1 d . . . C14 C 0.04786(9) 1.3109(2) -0.00319(14) 0.0340(5) Uani 1 1 d . . . H14 H 0.0448 1.3329 0.0404 0.041 Uiso 1 1 calc R . . C15 C 0.01145(9) 1.3847(2) -0.07842(14) 0.0375(6) Uani 1 1 d . . . H15 H -0.0162 1.4547 -0.0857 0.045 Uiso 1 1 calc R . . C16 C 0.01507(10) 1.3570(2) -0.14290(14) 0.0404(6) Uani 1 1 d . . . H16 H -0.0098 1.4075 -0.1946 0.048 Uiso 1 1 calc R . . C17 C 0.05549(10) 1.2543(2) -0.13093(14) 0.0392(6) Uani 1 1 d . . . H17 H 0.0588 1.2344 -0.1746 0.047 Uiso 1 1 calc R . . C18 C 0.09089(9) 1.1808(2) -0.05625(14) 0.0352(5) Uani 1 1 d . . . H18 H 0.1179 1.1101 -0.0501 0.042 Uiso 1 1 calc R . . C20 C 0.17009(9) 0.8797(2) 0.07431(13) 0.0295(5) Uani 1 1 d . . . H20 H 0.2117 0.9094 0.1064 0.035 Uiso 1 1 calc R . . C22 C 0.08609(9) 0.7543(2) -0.00748(14) 0.0373(6) Uani 1 1 d . . . H22 H 0.0581 0.6813 -0.0426 0.045 Uiso 1 1 calc R . . C23 C 0.07301(9) 0.8728(2) 0.01547(14) 0.0367(6) Uani 1 1 d . . . H23 H 0.0335 0.8983 -0.0014 0.044 Uiso 1 1 calc R . . C24 C 0.18269(9) 0.6592(2) 0.02008(13) 0.0290(5) Uani 1 1 d . . . C25 C 0.15218(10) 0.5702(2) -0.04903(14) 0.0372(5) Uani 1 1 d . . . H25 H 0.1087 0.5737 -0.0891 0.045 Uiso 1 1 calc R . . C26 C 0.18549(11) 0.4758(2) -0.05956(15) 0.0417(6) Uani 1 1 d . . . H26 H 0.1647 0.4134 -0.1066 0.050 Uiso 1 1 calc R . . C27 C 0.24881(11) 0.4717(2) -0.00213(15) 0.0411(6) Uani 1 1 d . . . H27 H 0.2716 0.4075 -0.0098 0.049 Uiso 1 1 calc R . . C28 C 0.27855(10) 0.5612(2) 0.06621(15) 0.0402(6) Uani 1 1 d . . . H28 H 0.3221 0.5587 0.1057 0.048 Uiso 1 1 calc R . . C29 C 0.24590(9) 0.6548(2) 0.07825(14) 0.0350(5) Uani 1 1 d . . . H29 H 0.2668 0.7154 0.1261 0.042 Uiso 1 1 calc R . . B1 B 0.13110(10) 1.1136(2) 0.09890(16) 0.0306(6) Uani 1 1 d . . . N19 N 0.12580(7) 0.95166(17) 0.06730(10) 0.0293(4) Uani 1 1 d . . . N21 N 0.14804(7) 0.75897(16) 0.02972(10) 0.0286(4) Uani 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 C1 0.0326(11) 0.0258(11) 0.0299(13) -0.0040(10) 0.0214(10) -0.0005(9) C2 0.0315(11) 0.0301(12) 0.0321(13) -0.0002(10) 0.0193(11) 0.0015(10) C3 0.0357(12) 0.0347(13) 0.0479(16) -0.0054(11) 0.0273(12) -0.0071(10) C4 0.0277(11) 0.0388(13) 0.0410(15) -0.0086(11) 0.0170(11) -0.0012(10) C5 0.0346(12) 0.0344(13) 0.0282(13) -0.0025(10) 0.0136(11) 0.0042(10) C6 0.0381(12) 0.0321(13) 0.0321(14) -0.0018(10) 0.0220(11) -0.0021(10) C7 0.0239(10) 0.0331(12) 0.0291(13) 0.0014(10) 0.0144(10) 0.0010(9) C8 0.0300(11) 0.0421(13) 0.0323(13) 0.0024(10) 0.0173(11) 0.0002(10) C9 0.0334(12) 0.0700(18) 0.0402(15) 0.0080(14) 0.0237(12) -0.0058(12) C10 0.0377(13) 0.081(2) 0.0387(15) -0.0024(14) 0.0267(12) 0.0011(13) C11 0.0477(14) 0.0537(16) 0.0391(15) -0.0091(12) 0.0281(13) 0.0028(12) C12 0.0414(13) 0.0395(14) 0.0377(14) -0.0037(11) 0.0260(12) -0.0031(11) C13 0.0250(11) 0.0277(12) 0.0306(13) -0.0044(9) 0.0161(10) -0.0038(9) C14 0.0335(11) 0.0306(12) 0.0385(14) -0.0045(10) 0.0223(11) -0.0032(10) C15 0.0320(12) 0.0308(13) 0.0411(15) 0.0014(11) 0.0179(11) 0.0032(10) C16 0.0379(12) 0.0368(13) 0.0314(14) 0.0031(11) 0.0134(11) 0.0009(11) C17 0.0398(13) 0.0434(14) 0.0284(14) -0.0004(11) 0.0177(11) 0.0012(11) C18 0.0338(12) 0.0359(13) 0.0353(14) -0.0017(11) 0.0209(11) 0.0023(10) C20 0.0284(11) 0.0312(12) 0.0299(13) -0.0005(10) 0.0183(10) -0.0032(10) C22 0.0280(11) 0.0346(13) 0.0409(15) -0.0079(11) 0.0168(11) -0.0049(10) C23 0.0268(11) 0.0332(13) 0.0417(14) -0.0061(11) 0.0167(11) -0.0035(10) C24 0.0353(12) 0.0249(11) 0.0305(13) 0.0015(10) 0.0221(11) -0.0005(9) C25 0.0348(12) 0.0394(13) 0.0354(14) -0.0037(11) 0.0205(11) -0.0012(10) C26 0.0517(14) 0.0380(14) 0.0416(15) -0.0080(11) 0.0316(13) -0.0032(11) C27 0.0504(14) 0.0378(14) 0.0511(16) 0.0041(12) 0.0392(13) 0.0061(11) C28 0.0374(12) 0.0406(14) 0.0436(15) 0.0030(12) 0.0252(12) 0.0032(11) C29 0.0353(12) 0.0331(12) 0.0334(13) 0.0004(10) 0.0193(11) 0.0012(10) B1 0.0304(12) 0.0268(13) 0.0342(15) -0.0035(11) 0.0195(12) -0.0005(11) N19 0.0272(9) 0.0286(10) 0.0306(10) -0.0002(8) 0.0169(8) -0.0005(8) N21 0.0276(9) 0.0275(10) 0.0291(10) -0.0032(8) 0.0164(8) -0.0017(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 C1 C6 1.398(3) . ? C1 C2 1.399(3) . ? C1 B1 1.634(3) . ? C2 C3 1.390(3) . ? C3 C4 1.383(3) . ? C4 C5 1.384(3) . ? C5 C6 1.385(3) . ? C7 C8 1.395(3) . ? C7 C12 1.409(3) . ? C7 B1 1.626(3) . ? C8 C9 1.392(3) . ? C9 C10 1.373(3) . ? C10 C11 1.382(3) . ? C11 C12 1.384(3) . ? C13 C14 1.405(3) . ? C13 C18 1.405(3) . ? C13 B1 1.634(3) . ? C14 C15 1.383(3) . ? C15 C16 1.378(3) . ? C16 C17 1.383(3) . ? C17 C18 1.373(3) . ? C20 N19 1.326(2) . ? C20 N21 1.345(2) . ? C22 C23 1.342(3) . ? C22 N21 1.381(2) . ? C23 N19 1.378(2) . ? C24 C29 1.380(3) . ? C24 C25 1.382(3) . ? C24 N21 1.435(2) . ? C25 C26 1.385(3) . ? C26 C27 1.381(3) . ? C27 C28 1.375(3) . ? C28 C29 1.383(3) . ? B1 N19 1.630(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 C6 C1 C2 116.25(18) . . ? C6 C1 B1 118.66(17) . . ? C2 C1 B1 125.07(18) . . ? C3 C2 C1 121.5(2) . . ? C4 C3 C2 120.67(19) . . ? C3 C4 C5 119.18(19) . . ? C4 C5 C6 119.7(2) . . ? C5 C6 C1 122.73(19) . . ? C8 C7 C12 115.13(18) . . ? C8 C7 B1 128.38(19) . . ? C12 C7 B1 116.49(18) . . ? C9 C8 C7 122.3(2) . . ? C10 C9 C8 120.7(2) . . ? C9 C10 C11 119.1(2) . . ? C10 C11 C12 119.9(2) . . ? C11 C12 C7 122.9(2) . . ? C14 C13 C18 114.41(19) . . ? C14 C13 B1 123.67(18) . . ? C18 C13 B1 121.90(18) . . ? C15 C14 C13 122.9(2) . . ? C16 C15 C14 120.3(2) . . ? C15 C16 C17 118.8(2) . . ? C18 C17 C16 120.3(2) . . ? C17 C18 C13 123.3(2) . . ? N19 C20 N21 110.73(17) . . ? C23 C22 N21 106.82(18) . . ? C22 C23 N19 109.33(17) . . ? C29 C24 C25 120.45(18) . . ? C29 C24 N21 120.26(18) . . ? C25 C24 N21 119.27(18) . . ? C24 C25 C26 119.5(2) . . ? C27 C26 C25 120.4(2) . . ? C28 C27 C26 119.4(2) . . ? C27 C28 C29 120.9(2) . . ? C24 C29 C28 119.3(2) . . ? C7 B1 N19 111.16(17) . . ? C7 B1 C13 112.32(16) . . ? N19 B1 C13 104.25(16) . . ? C7 B1 C1 108.92(17) . . ? N19 B1 C1 104.98(15) . . ? C13 B1 C1 114.88(17) . . ? C20 N19 C23 106.15(17) . . ? C20 N19 B1 125.68(16) . . ? C23 N19 B1 127.20(16) . . ? C20 N21 C22 106.97(16) . . ? C20 N21 C24 125.52(16) . . ? C22 N21 C24 127.43(17) . . ? 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 C6 C1 C2 C3 1.5(3) . . . . ? B1 C1 C2 C3 -177.05(18) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C4 C5 C6 C1 0.5(3) . . . . ? C2 C1 C6 C5 -1.6(3) . . . . ? B1 C1 C6 C5 177.04(18) . . . . ? C12 C7 C8 C9 0.3(3) . . . . ? B1 C7 C8 C9 -179.2(2) . . . . ? C7 C8 C9 C10 0.4(3) . . . . ? C8 C9 C10 C11 -0.3(4) . . . . ? C9 C10 C11 C12 -0.5(4) . . . . ? C10 C11 C12 C7 1.2(3) . . . . ? C8 C7 C12 C11 -1.1(3) . . . . ? B1 C7 C12 C11 178.5(2) . . . . ? C18 C13 C14 C15 0.5(3) . . . . ? B1 C13 C14 C15 -178.14(18) . . . . ? C13 C14 C15 C16 -0.7(3) . . . . ? C14 C15 C16 C17 0.2(3) . . . . ? C15 C16 C17 C18 0.5(3) . . . . ? C16 C17 C18 C13 -0.7(3) . . . . ? C14 C13 C18 C17 0.2(3) . . . . ? B1 C13 C18 C17 178.87(19) . . . . ? N21 C22 C23 N19 -0.6(2) . . . . ? C29 C24 C25 C26 0.2(3) . . . . ? N21 C24 C25 C26 178.70(18) . . . . ? C24 C25 C26 C27 -0.9(3) . . . . ? C25 C26 C27 C28 0.7(3) . . . . ? C26 C27 C28 C29 0.2(3) . . . . ? C25 C24 C29 C28 0.7(3) . . . . ? N21 C24 C29 C28 -177.82(18) . . . . ? C27 C28 C29 C24 -0.9(3) . . . . ? C8 C7 B1 N19 -10.5(3) . . . . ? C12 C7 B1 N19 170.02(17) . . . . ? C8 C7 B1 C13 105.9(2) . . . . ? C12 C7 B1 C13 -73.6(2) . . . . ? C8 C7 B1 C1 -125.7(2) . . . . ? C12 C7 B1 C1 54.8(2) . . . . ? C14 C13 B1 C7 15.9(3) . . . . ? C18 C13 B1 C7 -162.61(18) . . . . ? C14 C13 B1 N19 136.35(18) . . . . ? C18 C13 B1 N19 -42.1(2) . . . . ? C14 C13 B1 C1 -109.3(2) . . . . ? C18 C13 B1 C1 72.2(2) . . . . ? C6 C1 B1 C7 51.1(2) . . . . ? C2 C1 B1 C7 -130.4(2) . . . . ? C6 C1 B1 N19 -68.1(2) . . . . ? C2 C1 B1 N19 110.5(2) . . . . ? C6 C1 B1 C13 178.04(17) . . . . ? C2 C1 B1 C13 -3.4(3) . . . . ? N21 C20 N19 C23 -0.2(2) . . . . ? N21 C20 N19 B1 -169.55(17) . . . . ? C22 C23 N19 C20 0.5(2) . . . . ? C22 C23 N19 B1 169.65(19) . . . . ? C7 B1 N19 C20 -130.73(19) . . . . ? C13 B1 N19 C20 108.0(2) . . . . ? C1 B1 N19 C20 -13.1(3) . . . . ? C7 B1 N19 C23 62.1(3) . . . . ? C13 B1 N19 C23 -59.1(2) . . . . ? C1 B1 N19 C23 179.76(18) . . . . ? N19 C20 N21 C22 -0.2(2) . . . . ? N19 C20 N21 C24 176.87(17) . . . . ? C23 C22 N21 C20 0.5(2) . . . . ? C23 C22 N21 C24 -176.49(19) . . . . ? C29 C24 N21 C20 22.2(3) . . . . ? C25 C24 N21 C20 -156.33(19) . . . . ? C29 C24 N21 C22 -161.4(2) . . . . ? C25 C24 N21 C22 20.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.193 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.041 #===END data_comp11 _database_code_CSD 156980 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H19 B N2' _chemical_formula_weight 322.20 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 P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 7.1341(9) _cell_length_b 15.305(2) _cell_length_c 15.559(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.138(8) _cell_angle_gamma 90.00 _cell_volume 1698.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173.0(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9609 _exptl_absorpt_correction_T_max 0.9891 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(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 7443 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0723 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.90 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2931 _reflns_number_gt 2199 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Shedrick, 1997)' _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^)+(0.0457P)^2^+1.2460P] 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 2931 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1049 _refine_ls_R_factor_gt 0.0751 _refine_ls_wR_factor_ref 0.1781 _refine_ls_wR_factor_gt 0.1622 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _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 C1 C 0.4588(4) 1.06508(17) 0.69349(18) 0.0335(6) Uani 1 1 d . . . C2 C 0.4429(4) 1.07709(19) 0.60517(19) 0.0407(7) Uani 1 1 d . . . H2 H 0.3475 1.0465 0.5749 0.049 Uiso 1 1 calc R . . C3 C 0.5614(5) 1.1321(2) 0.5596(2) 0.0569(9) Uani 1 1 d . . . H3 H 0.5458 1.1382 0.4992 0.068 Uiso 1 1 calc R . . C4 C 0.6992(5) 1.1773(2) 0.6004(3) 0.0613(10) Uani 1 1 d . . . H4 H 0.7789 1.2155 0.5691 0.074 Uiso 1 1 calc R . . C5 C 0.7221(5) 1.1671(2) 0.6876(3) 0.0601(10) Uani 1 1 d . . . H5 H 0.8181 1.1982 0.7170 0.072 Uiso 1 1 calc R . . C6 C 0.6048(4) 1.1112(2) 0.7328(2) 0.0479(8) Uani 1 1 d . . . H6 H 0.6245 1.1041 0.7928 0.057 Uiso 1 1 calc R . . C7 C 0.4591(4) 0.93466(17) 0.80683(18) 0.0343(6) Uani 1 1 d . . . C8 C 0.6040(4) 0.8885(2) 0.7675(2) 0.0476(8) Uani 1 1 d . . . H8 H 0.6228 0.8957 0.7075 0.057 Uiso 1 1 calc R . . C9 C 0.7219(5) 0.8327(2) 0.8124(3) 0.0601(10) Uani 1 1 d . . . H9 H 0.8180 0.8018 0.7830 0.072 Uiso 1 1 calc R . . C10 C 0.6994(5) 0.8222(2) 0.8993(3) 0.0608(10) Uani 1 1 d . . . H10 H 0.7786 0.7836 0.9305 0.073 Uiso 1 1 calc R . . C11 C 0.5606(5) 0.8682(2) 0.9407(2) 0.0563(9) Uani 1 1 d . . . H11 H 0.5458 0.8625 1.0011 0.068 Uiso 1 1 calc R . . C12 C 0.4425(4) 0.92288(19) 0.89481(19) 0.0424(7) Uani 1 1 d . . . H12 H 0.3467 0.9534 0.9247 0.051 Uiso 1 1 calc R . . C13 C 0.1857(3) 1.05379(15) 0.81317(16) 0.0257(6) Uani 1 1 d . . . C14 C 0.2007(4) 1.14140(19) 0.8308(2) 0.0434(7) Uani 1 1 d . . . H14 H 0.2983 1.1743 0.8048 0.052 Uiso 1 1 calc R . . C15 C 0.0777(5) 1.1826(2) 0.8852(2) 0.0567(9) Uani 1 1 d . . . H15 H 0.0928 1.2432 0.8963 0.068 Uiso 1 1 calc R . . C16 C -0.0635(4) 1.1392(2) 0.9231(2) 0.0500(8) Uani 1 1 d . . . H16 H -0.1488 1.1687 0.9598 0.060 Uiso 1 1 calc R . . C17 C -0.0814(4) 1.0529(2) 0.9079(2) 0.0532(9) Uani 1 1 d . . . H17 H -0.1794 1.0209 0.9346 0.064 Uiso 1 1 calc R . . C18 C 0.0425(4) 1.0107(2) 0.8534(2) 0.0423(7) Uani 1 1 d . . . H18 H 0.0277 0.9498 0.8437 0.051 Uiso 1 1 calc R . . C20 C 0.2008(4) 0.85883(18) 0.6694(2) 0.0435(7) Uani 1 1 d . . . H20 H 0.2989 0.8262 0.6955 0.052 Uiso 1 1 calc R . . C21 C 0.0772(5) 0.8169(2) 0.6144(2) 0.0562(9) Uani 1 1 d . . . H21 H 0.0925 0.7564 0.6031 0.067 Uiso 1 1 calc R . . C23 C -0.0795(4) 0.9477(2) 0.5919(2) 0.0491(8) Uani 1 1 d . . . H23 H -0.1755 0.9805 0.5644 0.059 Uiso 1 1 calc R . . C24 C 0.0428(4) 0.98941(19) 0.6466(2) 0.0406(7) Uani 1 1 d . . . H24 H 0.0277 1.0502 0.6566 0.049 Uiso 1 1 calc R . . B1 B 0.3296(4) 1.0001(2) 0.7498(2) 0.0356(7) Uani 1 1 d . . . N19 N 0.1854(3) 0.94621(16) 0.68718(16) 0.0418(6) Uani 1 1 d . . . N22 N -0.0658(4) 0.8613(2) 0.5764(2) 0.0715(9) Uani 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 C1 0.0305(15) 0.0326(14) 0.0373(15) -0.0038(12) -0.0007(11) 0.0015(11) C2 0.0391(17) 0.0420(17) 0.0409(17) 0.0057(13) -0.0003(13) -0.0018(13) C3 0.059(2) 0.057(2) 0.054(2) 0.0205(17) 0.0080(17) 0.0026(17) C4 0.059(2) 0.0394(19) 0.085(3) 0.0096(19) 0.025(2) -0.0053(16) C5 0.0439(19) 0.0476(19) 0.089(3) -0.028(2) 0.0166(18) -0.0157(15) C6 0.0407(17) 0.057(2) 0.0461(18) -0.0135(15) 0.0049(14) -0.0105(15) C7 0.0342(15) 0.0324(15) 0.0362(15) -0.0035(12) -0.0065(12) -0.0009(11) C8 0.0390(17) 0.056(2) 0.0481(18) -0.0136(15) -0.0092(14) 0.0090(14) C9 0.0437(19) 0.0466(19) 0.090(3) -0.0266(19) -0.0229(19) 0.0149(15) C10 0.058(2) 0.0393(19) 0.085(3) 0.0090(18) -0.031(2) 0.0051(16) C11 0.060(2) 0.055(2) 0.054(2) 0.0200(17) -0.0156(17) -0.0037(17) C12 0.0417(17) 0.0411(17) 0.0443(17) 0.0060(14) -0.0038(13) 0.0006(13) C13 0.0233(13) 0.0257(13) 0.0282(13) 0.0039(11) -0.0059(10) 0.0026(10) C14 0.0385(16) 0.0420(17) 0.0496(18) 0.0083(14) -0.0008(14) 0.0047(13) C15 0.052(2) 0.0417(18) 0.076(2) 0.0015(17) 0.0040(17) 0.0106(15) C16 0.0368(17) 0.0453(19) 0.068(2) -0.0051(16) 0.0098(15) 0.0166(14) C17 0.0334(17) 0.065(2) 0.061(2) 0.0042(18) 0.0012(15) -0.0004(15) C18 0.0379(16) 0.0421(17) 0.0468(18) 0.0016(14) -0.0048(14) -0.0017(13) C20 0.0404(16) 0.0345(16) 0.0558(19) 0.0073(14) -0.0043(14) -0.0031(13) C21 0.050(2) 0.0444(19) 0.074(2) 0.0047(17) -0.0107(17) -0.0113(15) C23 0.0371(17) 0.050(2) 0.061(2) 0.0015(16) -0.0075(15) -0.0023(14) C24 0.0314(15) 0.0382(16) 0.0522(18) 0.0020(14) -0.0031(13) 0.0028(12) B1 0.0320(16) 0.0375(17) 0.0372(17) 0.0035(13) -0.0014(14) 0.0006(13) N19 0.0394(14) 0.0421(14) 0.0441(14) 0.0038(12) 0.0012(11) -0.0026(11) N22 0.0570(19) 0.069(2) 0.089(2) -0.0028(18) -0.0155(17) -0.0159(16) _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 C1 C2 1.391(4) . ? C1 C6 1.398(4) . ? C1 B1 1.616(4) . ? C2 C3 1.389(4) . ? C3 C4 1.359(5) . ? C4 C5 1.376(5) . ? C5 C6 1.388(5) . ? C7 C12 1.386(4) . ? C7 C8 1.395(4) . ? C7 B1 1.625(4) . ? C8 C9 1.386(4) . ? C9 C10 1.371(5) . ? C10 C11 1.377(5) . ? C11 C12 1.384(4) . ? C13 C18 1.369(4) . ? C13 C14 1.373(4) . ? C13 B1 1.645(4) . ? C14 C15 1.374(5) . ? C15 C16 1.344(5) . ? C16 C17 1.347(5) . ? C17 C18 1.386(5) . ? C20 N19 1.370(4) . ? C20 C21 1.385(4) . ? C21 N22 1.359(4) . ? C23 N22 1.349(4) . ? C23 C24 1.375(4) . ? C24 N19 1.366(4) . ? B1 N19 1.637(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 115.1(3) . . ? C2 C1 B1 124.9(2) . . ? C6 C1 B1 120.0(3) . . ? C3 C2 C1 122.4(3) . . ? C4 C3 C2 120.7(3) . . ? C3 C4 C5 119.1(3) . . ? C4 C5 C6 119.9(3) . . ? C5 C6 C1 122.6(3) . . ? C12 C7 C8 115.6(3) . . ? C12 C7 B1 124.8(3) . . ? C8 C7 B1 119.6(3) . . ? C9 C8 C7 122.8(3) . . ? C10 C9 C8 119.7(3) . . ? C9 C10 C11 119.2(3) . . ? C10 C11 C12 120.3(3) . . ? C11 C12 C7 122.3(3) . . ? C18 C13 C14 115.9(3) . . ? C18 C13 B1 120.1(2) . . ? C14 C13 B1 124.0(2) . . ? C13 C14 C15 121.4(3) . . ? C16 C15 C14 121.6(3) . . ? C15 C16 C17 118.6(3) . . ? C16 C17 C18 120.2(3) . . ? C13 C18 C17 122.3(3) . . ? N19 C20 C21 121.7(3) . . ? N22 C21 C20 120.9(3) . . ? N22 C23 C24 121.3(3) . . ? N19 C24 C23 122.2(3) . . ? C1 B1 C7 110.5(2) . . ? C1 B1 N19 110.3(2) . . ? C7 B1 N19 111.7(2) . . ? C1 B1 C13 112.0(2) . . ? C7 B1 C13 109.6(2) . . ? N19 B1 C13 102.5(2) . . ? C24 N19 C20 116.1(2) . . ? C24 N19 B1 119.8(2) . . ? C20 N19 B1 124.1(2) . . ? C23 N22 C21 117.8(3) . . ? 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 C6 C1 C2 C3 -1.1(4) . . . . ? B1 C1 C2 C3 -178.2(3) . . . . ? C1 C2 C3 C4 -0.2(5) . . . . ? C2 C3 C4 C5 0.8(5) . . . . ? C3 C4 C5 C6 -0.1(5) . . . . ? C4 C5 C6 C1 -1.3(5) . . . . ? C2 C1 C6 C5 1.8(4) . . . . ? B1 C1 C6 C5 179.1(3) . . . . ? C12 C7 C8 C9 1.5(4) . . . . ? B1 C7 C8 C9 179.0(3) . . . . ? C7 C8 C9 C10 -0.9(5) . . . . ? C8 C9 C10 C11 -0.7(5) . . . . ? C9 C10 C11 C12 1.5(5) . . . . ? C10 C11 C12 C7 -0.8(5) . . . . ? C8 C7 C12 C11 -0.7(4) . . . . ? B1 C7 C12 C11 -177.9(3) . . . . ? C18 C13 C14 C15 -0.4(4) . . . . ? B1 C13 C14 C15 -179.1(3) . . . . ? C13 C14 C15 C16 -0.5(5) . . . . ? C14 C15 C16 C17 1.1(5) . . . . ? C15 C16 C17 C18 -0.8(5) . . . . ? C14 C13 C18 C17 0.8(4) . . . . ? B1 C13 C18 C17 179.5(3) . . . . ? C16 C17 C18 C13 -0.2(5) . . . . ? N19 C20 C21 N22 -0.5(5) . . . . ? N22 C23 C24 N19 0.9(5) . . . . ? C2 C1 B1 C7 127.3(3) . . . . ? C6 C1 B1 C7 -49.7(4) . . . . ? C2 C1 B1 N19 3.3(4) . . . . ? C6 C1 B1 N19 -173.7(2) . . . . ? C2 C1 B1 C13 -110.2(3) . . . . ? C6 C1 B1 C13 72.8(3) . . . . ? C12 C7 B1 C1 127.2(3) . . . . ? C8 C7 B1 C1 -49.9(4) . . . . ? C12 C7 B1 N19 -109.6(3) . . . . ? C8 C7 B1 N19 73.3(3) . . . . ? C12 C7 B1 C13 3.3(4) . . . . ? C8 C7 B1 C13 -173.9(2) . . . . ? C18 C13 B1 C1 167.8(2) . . . . ? C14 C13 B1 C1 -13.5(4) . . . . ? C18 C13 B1 C7 -69.1(3) . . . . ? C14 C13 B1 C7 109.6(3) . . . . ? C18 C13 B1 N19 49.7(3) . . . . ? C14 C13 B1 N19 -131.7(3) . . . . ? C23 C24 N19 C20 0.7(4) . . . . ? C23 C24 N19 B1 178.5(3) . . . . ? C21 C20 N19 C24 -0.8(4) . . . . ? C21 C20 N19 B1 -178.5(3) . . . . ? C1 B1 N19 C24 -68.7(3) . . . . ? C7 B1 N19 C24 167.9(3) . . . . ? C13 B1 N19 C24 50.7(3) . . . . ? C1 B1 N19 C20 108.9(3) . . . . ? C7 B1 N19 C20 -14.5(4) . . . . ? C13 B1 N19 C20 -131.7(3) . . . . ? C24 C23 N22 C21 -2.2(5) . . . . ? C20 C21 N22 C23 2.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.287 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.044 #===END data_comp1 _database_code_CSD 156981 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H28 B N3' _chemical_formula_weight 429.35 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 P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.0245(3) _cell_length_b 12.7797(4) _cell_length_c 19.0370(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2438.83(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173.0(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 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9798 _exptl_absorpt_correction_T_max 0.9966 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(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 10987 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.78 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4255 _reflns_number_gt 3969 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'shelxs-97 (sheldrick, 1997)' _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^)+(0.0627P)^2^+0.4169P] 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 0(3) _refine_ls_number_reflns 4255 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1127 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _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 C1 C 0.78121(18) 0.34457(13) -0.09052(8) 0.0322(4) Uani 1 1 d . . . C2 C 0.9067(2) 0.29972(14) -0.07941(10) 0.0381(4) Uani 1 1 d . . . H2 H 0.9831 0.3436 -0.0810 0.046 Uiso 1 1 calc R . . C3 C 0.9243(2) 0.19350(15) -0.06617(11) 0.0463(5) Uani 1 1 d . . . H3 H 1.0114 0.1664 -0.0588 0.056 Uiso 1 1 calc R . . C4 C 0.8158(3) 0.12775(16) -0.06366(11) 0.0514(5) Uani 1 1 d . . . H4 H 0.8275 0.0549 -0.0557 0.062 Uiso 1 1 calc R . . C5 C 0.6895(3) 0.16899(17) -0.07296(11) 0.0517(6) Uani 1 1 d . . . H5 H 0.6136 0.1246 -0.0706 0.062 Uiso 1 1 calc R . . C6 C 0.6732(2) 0.27563(15) -0.08583(10) 0.0406(4) Uani 1 1 d . . . H6 H 0.5855 0.3025 -0.0916 0.049 Uiso 1 1 calc R . . C7 C 0.75703(18) 0.52111(12) -0.02264(8) 0.0307(4) Uani 1 1 d . . . C8 C 0.87205(19) 0.54753(15) 0.01501(10) 0.0384(4) Uani 1 1 d . . . H8 H 0.9565 0.5379 -0.0067 0.046 Uiso 1 1 calc R . . C9 C 0.8677(2) 0.58731(17) 0.08294(10) 0.0457(5) Uani 1 1 d . . . H9 H 0.9482 0.6053 0.1064 0.055 Uiso 1 1 calc R . . C10 C 0.7464(2) 0.60073(16) 0.11647(9) 0.0462(5) Uani 1 1 d . . . H10 H 0.7427 0.6285 0.1627 0.055 Uiso 1 1 calc R . . C11 C 0.6307(2) 0.57307(15) 0.08166(10) 0.0414(5) Uani 1 1 d . . . H11 H 0.5468 0.5811 0.1042 0.050 Uiso 1 1 calc R . . C12 C 0.63681(18) 0.53359(14) 0.01393(9) 0.0335(4) Uani 1 1 d . . . H12 H 0.5560 0.5142 -0.0087 0.040 Uiso 1 1 calc R . . C13 C 0.63228(17) 0.50249(14) -0.14915(9) 0.0323(4) Uani 1 1 d . . . C14 C 0.58838(19) 0.44052(17) -0.20515(9) 0.0411(5) Uani 1 1 d . . . H14 H 0.6288 0.3741 -0.2123 0.049 Uiso 1 1 calc R . . C15 C 0.4881(2) 0.4724(2) -0.25070(11) 0.0558(6) Uani 1 1 d . . . H15 H 0.4610 0.4276 -0.2879 0.067 Uiso 1 1 calc R . . C16 C 0.4274(2) 0.5685(3) -0.24235(12) 0.0660(8) Uani 1 1 d . . . H16 H 0.3594 0.5906 -0.2738 0.079 Uiso 1 1 calc R . . C17 C 0.4671(2) 0.6321(2) -0.18752(12) 0.0610(7) Uani 1 1 d . . . H17 H 0.4259 0.6983 -0.1808 0.073 Uiso 1 1 calc R . . C18 C 0.5678(2) 0.59913(17) -0.14210(11) 0.0429(5) Uani 1 1 d . . . H18 H 0.5937 0.6441 -0.1048 0.052 Uiso 1 1 calc R . . C19 C 0.88759(16) 0.52144(14) -0.14831(9) 0.0287(4) Uani 1 1 d . . . C20 C 0.92700(19) 0.62615(14) -0.14114(9) 0.0357(4) Uani 1 1 d . . . H20 H 0.8911 0.6656 -0.1033 0.043 Uiso 1 1 calc R . . C21 C 1.0154(2) 0.67520(17) -0.18619(11) 0.0429(5) Uani 1 1 d . . . H21 H 1.0380 0.7466 -0.1790 0.051 Uiso 1 1 calc R . . C22 C 1.0710(2) 0.62037(17) -0.24168(10) 0.0448(5) Uani 1 1 d . . . H22 H 1.1308 0.6537 -0.2733 0.054 Uiso 1 1 calc R . . C23 C 1.03790(18) 0.51658(18) -0.25017(10) 0.0421(5) Uani 1 1 d . . . H23 H 1.0768 0.4774 -0.2873 0.050 Uiso 1 1 calc R . . C24 C 0.94746(18) 0.46837(15) -0.20461(9) 0.0356(4) Uani 1 1 d . . . H24 H 0.9257 0.3969 -0.2120 0.043 Uiso 1 1 calc R . . C26 C 0.7595(2) 0.33249(16) 0.20485(10) 0.0468(5) Uani 1 1 d . . . H26 H 0.7515 0.3864 0.2389 0.056 Uiso 1 1 calc R . . C28 C 0.7716(2) 0.17997(16) 0.15491(11) 0.0504(5) Uani 1 1 d . . . H28 H 0.7733 0.1062 0.1489 0.061 Uiso 1 1 calc R . . C29 C 0.7813(2) 0.25054(18) 0.10492(10) 0.0509(5) Uani 1 1 d . . . H29 H 0.7917 0.2376 0.0561 0.061 Uiso 1 1 calc R . . B1 B 0.7642(2) 0.47104(15) -0.10226(9) 0.0299(4) Uani 1 1 d . . . N25 N 0.77372(19) 0.34528(13) 0.13648(9) 0.0506(4) Uani 1 1 d . . . H25 H 0.7776 0.4060 0.1148 0.061 Uiso 1 1 calc R . . N27 N 0.75862(19) 0.23196(14) 0.21691(8) 0.0494(4) Uani 1 1 d . . . H27 H 0.7508 0.2025 0.2585 0.059 Uiso 1 1 calc R . . N100 N 0.7591(2) 0.14520(14) 0.37040(11) 0.0608(5) Uani 1 1 d . . . C101 C 0.7588(2) 0.15294(15) 0.42971(12) 0.0503(5) Uani 1 1 d . . . C102 C 0.7566(3) 0.1641(2) 0.50529(13) 0.0777(8) Uani 1 1 d . . . H10A H 0.6654 0.1539 0.5225 0.117 Uiso 1 1 calc R . . H10B H 0.7875 0.2344 0.5181 0.117 Uiso 1 1 calc R . . H10C H 0.8155 0.1117 0.5265 0.117 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 C1 0.0381(10) 0.0328(8) 0.0257(8) -0.0013(7) 0.0022(7) -0.0011(7) C2 0.0405(10) 0.0343(9) 0.0394(10) 0.0021(7) 0.0037(8) 0.0029(8) C3 0.0571(13) 0.0364(10) 0.0455(12) 0.0031(8) 0.0064(10) 0.0106(10) C4 0.0777(16) 0.0306(10) 0.0459(12) 0.0005(8) 0.0023(10) 0.0034(10) C5 0.0679(15) 0.0415(11) 0.0455(12) 0.0023(9) -0.0022(10) -0.0212(11) C6 0.0430(10) 0.0404(10) 0.0383(10) 0.0016(8) -0.0018(8) -0.0087(8) C7 0.0353(9) 0.0271(8) 0.0298(8) 0.0032(6) 0.0003(8) -0.0002(8) C8 0.0345(10) 0.0484(11) 0.0323(10) 0.0009(8) -0.0027(8) 0.0005(8) C9 0.0456(11) 0.0577(12) 0.0338(10) -0.0007(9) -0.0089(8) -0.0031(10) C10 0.0579(13) 0.0515(11) 0.0291(9) -0.0053(8) -0.0008(9) 0.0001(11) C11 0.0449(11) 0.0440(11) 0.0351(10) -0.0009(8) 0.0068(8) 0.0041(9) C12 0.0355(9) 0.0342(9) 0.0309(9) -0.0005(7) 0.0015(7) -0.0011(8) C13 0.0271(9) 0.0416(10) 0.0283(9) 0.0041(7) 0.0032(7) -0.0026(7) C14 0.0363(10) 0.0596(12) 0.0273(9) -0.0021(8) 0.0019(8) -0.0071(9) C15 0.0370(11) 0.1025(19) 0.0279(10) -0.0017(11) 0.0004(8) -0.0134(12) C16 0.0322(11) 0.128(2) 0.0381(12) 0.0155(14) -0.0017(9) 0.0118(14) C17 0.0475(13) 0.0862(18) 0.0492(13) 0.0136(12) 0.0005(10) 0.0287(12) C18 0.0397(10) 0.0513(12) 0.0378(10) 0.0047(9) -0.0027(9) 0.0090(10) C19 0.0267(8) 0.0330(8) 0.0265(8) 0.0011(7) -0.0024(6) 0.0021(7) C20 0.0380(10) 0.0362(9) 0.0328(9) -0.0018(7) -0.0001(8) -0.0004(8) C21 0.0403(11) 0.0437(11) 0.0446(11) 0.0029(8) -0.0016(8) -0.0087(9) C22 0.0322(9) 0.0586(13) 0.0437(11) 0.0088(9) 0.0038(8) -0.0040(9) C23 0.0344(10) 0.0598(13) 0.0321(10) -0.0015(9) 0.0044(8) 0.0073(9) C24 0.0347(10) 0.0379(10) 0.0343(10) -0.0036(8) -0.0008(7) 0.0028(8) C26 0.0509(12) 0.0459(11) 0.0438(10) -0.0081(8) -0.0022(10) 0.0062(10) C28 0.0563(14) 0.0418(11) 0.0532(12) -0.0075(9) -0.0070(10) 0.0046(10) C29 0.0507(13) 0.0674(14) 0.0346(10) -0.0079(10) -0.0035(9) 0.0143(11) B1 0.0293(10) 0.0316(9) 0.0288(9) -0.0008(7) -0.0010(8) 0.0016(8) N25 0.0563(11) 0.0461(10) 0.0495(10) 0.0121(8) -0.0024(8) 0.0053(9) N27 0.0546(10) 0.0552(10) 0.0382(8) 0.0077(7) 0.0034(8) 0.0025(9) N100 0.0674(13) 0.0444(10) 0.0706(13) -0.0029(9) 0.0129(11) 0.0035(10) C101 0.0494(12) 0.0345(10) 0.0669(14) -0.0067(9) 0.0061(11) 0.0011(9) C102 0.090(2) 0.0718(16) 0.0716(16) -0.0182(13) -0.0014(16) 0.0051(16) _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 C1 C2 1.398(3) . ? C1 C6 1.399(3) . ? C1 B1 1.641(2) . ? C2 C3 1.392(3) . ? C3 C4 1.375(3) . ? C4 C5 1.383(3) . ? C5 C6 1.394(3) . ? C7 C8 1.399(3) . ? C7 C12 1.401(2) . ? C7 B1 1.647(2) . ? C8 C9 1.390(3) . ? C9 C10 1.384(3) . ? C10 C11 1.382(3) . ? C11 C12 1.386(3) . ? C13 C14 1.399(3) . ? C13 C18 1.400(3) . ? C13 B1 1.645(2) . ? C14 C15 1.389(3) . ? C15 C16 1.381(4) . ? C16 C17 1.381(4) . ? C17 C18 1.394(3) . ? C19 C20 1.402(2) . ? C19 C24 1.403(2) . ? C19 B1 1.647(2) . ? C20 C21 1.383(3) . ? C21 C22 1.385(3) . ? C22 C23 1.377(3) . ? C23 C24 1.398(3) . ? C26 N27 1.305(3) . ? C26 N25 1.319(3) . ? C28 C29 1.315(3) . ? C28 N27 1.361(3) . ? C29 N25 1.354(3) . ? N100 C101 1.133(3) . ? C101 C102 1.446(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 C2 C1 C6 115.38(16) . . ? C2 C1 B1 121.19(15) . . ? C6 C1 B1 123.28(16) . . ? C3 C2 C1 122.76(19) . . ? C4 C3 C2 120.1(2) . . ? C3 C4 C5 119.12(18) . . ? C4 C5 C6 120.2(2) . . ? C5 C6 C1 122.4(2) . . ? C8 C7 C12 115.28(14) . . ? C8 C7 B1 121.96(16) . . ? C12 C7 B1 122.63(15) . . ? C9 C8 C7 122.63(18) . . ? C10 C9 C8 120.10(18) . . ? C11 C10 C9 118.99(16) . . ? C10 C11 C12 120.16(18) . . ? C11 C12 C7 122.79(17) . . ? C14 C13 C18 115.28(17) . . ? C14 C13 B1 121.87(16) . . ? C18 C13 B1 122.31(16) . . ? C15 C14 C13 122.5(2) . . ? C16 C15 C14 120.5(2) . . ? C15 C16 C17 118.9(2) . . ? C16 C17 C18 120.0(2) . . ? C17 C18 C13 122.8(2) . . ? C20 C19 C24 114.54(16) . . ? C20 C19 B1 122.21(15) . . ? C24 C19 B1 122.59(15) . . ? C21 C20 C19 123.55(18) . . ? C20 C21 C22 120.11(19) . . ? C23 C22 C21 118.67(19) . . ? C22 C23 C24 120.54(18) . . ? C23 C24 C19 122.57(18) . . ? N27 C26 N25 107.24(17) . . ? C29 C28 N27 107.46(18) . . ? C28 C29 N25 106.74(17) . . ? C1 B1 C13 113.45(14) . . ? C1 B1 C7 105.18(12) . . ? C13 B1 C7 111.67(14) . . ? C1 B1 C19 112.32(14) . . ? C13 B1 C19 102.67(12) . . ? C7 B1 C19 111.76(13) . . ? C26 N25 C29 109.46(18) . . ? C26 N27 C28 109.11(16) . . ? N100 C101 C102 179.0(3) . . ? 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 C6 C1 C2 C3 1.4(3) . . . . ? B1 C1 C2 C3 177.07(17) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C5 -1.4(3) . . . . ? C3 C4 C5 C6 1.1(3) . . . . ? C4 C5 C6 C1 0.6(3) . . . . ? C2 C1 C6 C5 -1.7(3) . . . . ? B1 C1 C6 C5 -177.30(17) . . . . ? C12 C7 C8 C9 -2.4(3) . . . . ? B1 C7 C8 C9 -178.29(17) . . . . ? C7 C8 C9 C10 1.0(3) . . . . ? C8 C9 C10 C11 0.6(3) . . . . ? C9 C10 C11 C12 -0.7(3) . . . . ? C10 C11 C12 C7 -0.9(3) . . . . ? C8 C7 C12 C11 2.4(2) . . . . ? B1 C7 C12 C11 178.21(16) . . . . ? C18 C13 C14 C15 0.1(3) . . . . ? B1 C13 C14 C15 -171.62(17) . . . . ? C13 C14 C15 C16 0.4(3) . . . . ? C14 C15 C16 C17 -0.7(3) . . . . ? C15 C16 C17 C18 0.5(4) . . . . ? C16 C17 C18 C13 -0.1(3) . . . . ? C14 C13 C18 C17 -0.2(3) . . . . ? B1 C13 C18 C17 171.46(19) . . . . ? C24 C19 C20 C21 1.3(3) . . . . ? B1 C19 C20 C21 -169.59(17) . . . . ? C19 C20 C21 C22 -0.6(3) . . . . ? C20 C21 C22 C23 -0.9(3) . . . . ? C21 C22 C23 C24 1.5(3) . . . . ? C22 C23 C24 C19 -0.7(3) . . . . ? C20 C19 C24 C23 -0.7(3) . . . . ? B1 C19 C24 C23 170.19(16) . . . . ? N27 C28 C29 N25 -0.2(2) . . . . ? C2 C1 B1 C13 152.97(16) . . . . ? C6 C1 B1 C13 -31.7(2) . . . . ? C2 C1 B1 C7 -84.71(19) . . . . ? C6 C1 B1 C7 90.60(18) . . . . ? C2 C1 B1 C19 37.1(2) . . . . ? C6 C1 B1 C19 -147.62(16) . . . . ? C14 C13 B1 C1 -35.9(2) . . . . ? C18 C13 B1 C1 153.02(16) . . . . ? C14 C13 B1 C7 -154.54(15) . . . . ? C18 C13 B1 C7 34.4(2) . . . . ? C14 C13 B1 C19 85.58(19) . . . . ? C18 C13 B1 C19 -85.51(19) . . . . ? C8 C7 B1 C1 86.06(19) . . . . ? C12 C7 B1 C1 -89.47(18) . . . . ? C8 C7 B1 C13 -150.46(16) . . . . ? C12 C7 B1 C13 34.0(2) . . . . ? C8 C7 B1 C19 -36.1(2) . . . . ? C12 C7 B1 C19 148.38(16) . . . . ? C20 C19 B1 C1 -152.69(15) . . . . ? C24 C19 B1 C1 37.2(2) . . . . ? C20 C19 B1 C13 85.08(18) . . . . ? C24 C19 B1 C13 -85.07(19) . . . . ? C20 C19 B1 C7 -34.7(2) . . . . ? C24 C19 B1 C7 155.11(15) . . . . ? N27 C26 N25 C29 0.3(3) . . . . ? C28 C29 N25 C26 0.0(3) . . . . ? N25 C26 N27 C28 -0.4(3) . . . . ? C29 C28 N27 C26 0.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N27 H27 N100 0.88 2.25 3.125(3) 170.3 . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.669 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.034 #===END data_comp6 _database_code_CSD 156982 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 B N2' _chemical_formula_weight 310.19 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 c2/c 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' '-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 24.3436(8) _cell_length_b 11.0632(4) _cell_length_c 16.4744(6) _cell_angle_alpha 90.00 _cell_angle_beta 130.343(2) _cell_angle_gamma 90.00 _cell_volume 3381.7(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173.0(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 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9655 _exptl_absorpt_correction_T_max 0.9860 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(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 7416 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.03 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2937 _reflns_number_gt 2723 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'shelxs-97 (Sheldrick, 1997)' _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^)+(0.0261P)^2^+2.0122P] 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 2937 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0877 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 C1 C 0.28137(6) 0.49960(10) 0.60612(9) 0.0220(3) Uani 1 1 d . . . C2 C 0.31299(6) 0.40191(11) 0.59504(10) 0.0264(3) Uani 1 1 d . . . H2 H 0.2832 0.3519 0.5338 0.032 Uiso 1 1 calc R . . C3 C 0.38588(7) 0.37567(12) 0.66983(10) 0.0298(3) Uani 1 1 d . . . H3 H 0.4051 0.3080 0.6600 0.036 Uiso 1 1 calc R . . C4 C 0.43065(7) 0.44840(12) 0.75891(10) 0.0309(3) Uani 1 1 d . . . H4 H 0.4806 0.4304 0.8111 0.037 Uiso 1 1 calc R . . C5 C 0.40206(7) 0.54726(12) 0.77114(10) 0.0303(3) Uani 1 1 d . . . H5 H 0.4326 0.5988 0.8311 0.036 Uiso 1 1 calc R . . C6 C 0.32864(6) 0.57181(11) 0.69613(9) 0.0249(3) Uani 1 1 d . . . H6 H 0.3100 0.6400 0.7065 0.030 Uiso 1 1 calc R . . C7 C 0.16658(6) 0.65067(10) 0.52694(9) 0.0222(3) Uani 1 1 d . . . C8 C 0.17151(6) 0.67399(11) 0.61534(10) 0.0261(3) Uani 1 1 d . . . H8 H 0.1946 0.6162 0.6712 0.031 Uiso 1 1 calc R . . C9 C 0.14390(7) 0.77844(12) 0.62398(11) 0.0311(3) Uani 1 1 d . . . H9 H 0.1481 0.7908 0.6848 0.037 Uiso 1 1 calc R . . C10 C 0.11029(7) 0.86449(12) 0.54387(11) 0.0340(3) Uani 1 1 d . . . H10 H 0.0914 0.9361 0.5494 0.041 Uiso 1 1 calc R . . C11 C 0.10452(7) 0.84494(12) 0.45566(11) 0.0325(3) Uani 1 1 d . . . H11 H 0.0816 0.9034 0.4003 0.039 Uiso 1 1 calc R . . C12 C 0.13224(6) 0.73982(11) 0.44783(10) 0.0267(3) Uani 1 1 d . . . H12 H 0.1277 0.7281 0.3866 0.032 Uiso 1 1 calc R . . C13 C 0.14788(6) 0.41206(10) 0.51411(9) 0.0222(3) Uani 1 1 d . . . C14 C 0.17829(7) 0.30399(11) 0.57065(9) 0.0251(3) Uani 1 1 d . . . H14 H 0.2288 0.2926 0.6136 0.030 Uiso 1 1 calc R . . C15 C 0.13731(7) 0.21247(11) 0.56641(10) 0.0296(3) Uani 1 1 d . . . H15 H 0.1600 0.1403 0.6061 0.035 Uiso 1 1 calc R . . C16 C 0.06386(7) 0.22623(12) 0.50474(10) 0.0313(3) Uani 1 1 d . . . H16 H 0.0356 0.1635 0.5010 0.038 Uiso 1 1 calc R . . C17 C 0.03171(7) 0.33227(12) 0.44841(11) 0.0337(3) Uani 1 1 d . . . H17 H -0.0189 0.3427 0.4058 0.040 Uiso 1 1 calc R . . C18 C 0.07316(7) 0.42351(12) 0.45400(10) 0.0291(3) Uani 1 1 d . . . H18 H 0.0502 0.4963 0.4158 0.035 Uiso 1 1 calc R . . C21 C 0.19071(7) 0.58745(12) 0.29171(10) 0.0322(3) Uani 1 1 d . . . H21 H 0.2118 0.6236 0.2652 0.039 Uiso 1 1 calc R . . C22 C 0.12466(7) 0.53373(13) 0.23255(10) 0.0357(3) Uani 1 1 d . . . H22 H 0.0905 0.5253 0.1573 0.043 Uiso 1 1 calc R . . C23 C 0.11784(7) 0.49390(12) 0.30554(10) 0.0309(3) Uani 1 1 d . . . H23 H 0.0771 0.4523 0.2877 0.037 Uiso 1 1 calc R . . B1 B 0.19475(7) 0.52183(12) 0.51825(10) 0.0219(3) Uani 1 1 d . . . N19 N 0.17643(5) 0.52229(9) 0.40410(8) 0.0230(2) Uani 1 1 d . . . N20 N 0.22038(5) 0.57996(9) 0.39376(8) 0.0281(3) Uani 1 1 d . . . H20 H 0.2631 0.6089 0.4473 0.034 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 C1 0.0252(6) 0.0215(6) 0.0235(6) 0.0012(5) 0.0176(5) -0.0020(5) C2 0.0280(6) 0.0248(6) 0.0296(6) -0.0035(5) 0.0201(6) -0.0035(5) C3 0.0312(7) 0.0287(7) 0.0377(7) 0.0059(6) 0.0260(6) 0.0053(5) C4 0.0225(6) 0.0437(8) 0.0264(6) 0.0090(6) 0.0158(6) 0.0042(5) C5 0.0258(6) 0.0417(8) 0.0214(6) -0.0036(5) 0.0144(5) -0.0049(6) C6 0.0259(6) 0.0268(6) 0.0245(6) -0.0015(5) 0.0175(5) -0.0011(5) C7 0.0186(6) 0.0229(6) 0.0245(6) -0.0010(5) 0.0137(5) -0.0039(5) C8 0.0253(6) 0.0280(6) 0.0273(6) 0.0009(5) 0.0181(6) -0.0008(5) C9 0.0295(7) 0.0346(7) 0.0360(7) -0.0078(6) 0.0243(6) -0.0045(5) C10 0.0309(7) 0.0248(7) 0.0514(8) -0.0037(6) 0.0289(7) 0.0000(5) C11 0.0291(7) 0.0255(7) 0.0404(8) 0.0070(6) 0.0214(6) 0.0028(5) C12 0.0252(6) 0.0267(6) 0.0281(6) 0.0022(5) 0.0172(6) -0.0013(5) C13 0.0247(6) 0.0238(6) 0.0201(6) -0.0030(5) 0.0154(5) -0.0026(5) C14 0.0255(6) 0.0265(6) 0.0221(6) -0.0014(5) 0.0149(5) -0.0021(5) C15 0.0369(7) 0.0247(6) 0.0259(6) 0.0023(5) 0.0198(6) -0.0029(5) C16 0.0345(7) 0.0324(7) 0.0293(7) -0.0029(6) 0.0216(6) -0.0118(6) C17 0.0251(7) 0.0392(8) 0.0340(7) 0.0023(6) 0.0179(6) -0.0052(5) C18 0.0264(6) 0.0287(7) 0.0305(7) 0.0050(5) 0.0175(6) 0.0005(5) C21 0.0418(8) 0.0344(7) 0.0299(7) -0.0015(6) 0.0275(6) -0.0054(6) C22 0.0386(8) 0.0437(8) 0.0231(6) -0.0053(6) 0.0191(6) -0.0083(6) C23 0.0285(7) 0.0370(7) 0.0246(6) -0.0060(5) 0.0160(6) -0.0094(5) B1 0.0239(7) 0.0234(7) 0.0196(6) -0.0010(5) 0.0146(6) -0.0019(5) N19 0.0230(5) 0.0242(5) 0.0240(5) -0.0015(4) 0.0162(5) -0.0038(4) N20 0.0274(5) 0.0338(6) 0.0269(5) -0.0048(5) 0.0192(5) -0.0100(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 C1 C6 1.3971(17) . ? C1 C2 1.4056(17) . ? C1 B1 1.6281(17) . ? C2 C3 1.3858(17) . ? C3 C4 1.3849(19) . ? C4 C5 1.3794(19) . ? C5 C6 1.3913(17) . ? C7 C12 1.3998(17) . ? C7 C8 1.4054(16) . ? C7 B1 1.6278(17) . ? C8 C9 1.3897(17) . ? C9 C10 1.3855(19) . ? C10 C11 1.384(2) . ? C11 C12 1.3918(18) . ? C13 C14 1.3973(17) . ? C13 C18 1.4047(17) . ? C13 B1 1.6372(17) . ? C14 C15 1.3912(17) . ? C15 C16 1.3786(18) . ? C16 C17 1.3819(19) . ? C17 C18 1.3876(18) . ? C21 N20 1.3352(16) . ? C21 C22 1.3637(19) . ? C22 C23 1.3879(18) . ? C23 N19 1.3308(16) . ? B1 N19 1.6278(15) . ? N19 N20 1.3479(13) . ? 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 C6 C1 C2 115.69(11) . . ? C6 C1 B1 124.07(10) . . ? C2 C1 B1 120.24(10) . . ? C3 C2 C1 122.63(11) . . ? C4 C3 C2 119.79(12) . . ? C5 C4 C3 119.35(11) . . ? C4 C5 C6 120.30(12) . . ? C5 C6 C1 122.21(11) . . ? C12 C7 C8 115.74(11) . . ? C12 C7 B1 124.52(10) . . ? C8 C7 B1 119.58(10) . . ? C9 C8 C7 122.43(11) . . ? C10 C9 C8 120.03(12) . . ? C11 C10 C9 119.26(12) . . ? C10 C11 C12 120.15(12) . . ? C11 C12 C7 122.39(12) . . ? C14 C13 C18 115.63(11) . . ? C14 C13 B1 123.55(10) . . ? C18 C13 B1 120.80(10) . . ? C15 C14 C13 122.41(11) . . ? C16 C15 C14 120.16(12) . . ? C15 C16 C17 119.29(11) . . ? C16 C17 C18 120.11(12) . . ? C17 C18 C13 122.37(12) . . ? N20 C21 C22 107.41(11) . . ? C21 C22 C23 105.44(11) . . ? N19 C23 C22 110.32(11) . . ? C7 B1 N19 106.44(9) . . ? C7 B1 C1 115.53(10) . . ? N19 B1 C1 104.84(9) . . ? C7 B1 C13 109.34(9) . . ? N19 B1 C13 106.97(9) . . ? C1 B1 C13 113.06(10) . . ? C23 N19 N20 105.61(10) . . ? C23 N19 B1 133.19(10) . . ? N20 N19 B1 120.09(9) . . ? C21 N20 N19 111.22(10) . . ? 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 C6 C1 C2 C3 2.06(17) . . . . ? B1 C1 C2 C3 -177.08(11) . . . . ? C1 C2 C3 C4 -1.03(18) . . . . ? C2 C3 C4 C5 -0.90(18) . . . . ? C3 C4 C5 C6 1.67(18) . . . . ? C4 C5 C6 C1 -0.56(18) . . . . ? C2 C1 C6 C5 -1.26(17) . . . . ? B1 C1 C6 C5 177.84(11) . . . . ? C12 C7 C8 C9 0.28(17) . . . . ? B1 C7 C8 C9 -175.39(11) . . . . ? C7 C8 C9 C10 -0.29(18) . . . . ? C8 C9 C10 C11 0.12(19) . . . . ? C9 C10 C11 C12 0.04(19) . . . . ? C10 C11 C12 C7 -0.03(19) . . . . ? C8 C7 C12 C11 -0.12(17) . . . . ? B1 C7 C12 C11 175.31(11) . . . . ? C18 C13 C14 C15 1.15(17) . . . . ? B1 C13 C14 C15 179.47(11) . . . . ? C13 C14 C15 C16 0.10(18) . . . . ? C14 C15 C16 C17 -0.78(19) . . . . ? C15 C16 C17 C18 0.14(19) . . . . ? C16 C17 C18 C13 1.2(2) . . . . ? C14 C13 C18 C17 -1.81(18) . . . . ? B1 C13 C18 C17 179.82(11) . . . . ? N20 C21 C22 C23 -0.47(16) . . . . ? C21 C22 C23 N19 0.31(16) . . . . ? C12 C7 B1 N19 1.23(15) . . . . ? C8 C7 B1 N19 176.50(9) . . . . ? C12 C7 B1 C1 117.13(12) . . . . ? C8 C7 B1 C1 -67.60(14) . . . . ? C12 C7 B1 C13 -113.99(12) . . . . ? C8 C7 B1 C13 61.28(13) . . . . ? C6 C1 B1 C7 12.04(16) . . . . ? C2 C1 B1 C7 -168.89(10) . . . . ? C6 C1 B1 N19 128.85(11) . . . . ? C2 C1 B1 N19 -52.09(13) . . . . ? C6 C1 B1 C13 -114.99(12) . . . . ? C2 C1 B1 C13 64.08(14) . . . . ? C14 C13 B1 C7 -137.44(11) . . . . ? C18 C13 B1 C7 40.80(14) . . . . ? C14 C13 B1 N19 107.68(12) . . . . ? C18 C13 B1 N19 -74.08(13) . . . . ? C14 C13 B1 C1 -7.21(15) . . . . ? C18 C13 B1 C1 171.03(10) . . . . ? C22 C23 N19 N20 -0.03(15) . . . . ? C22 C23 N19 B1 167.45(12) . . . . ? C7 B1 N19 C23 -85.12(15) . . . . ? C1 B1 N19 C23 151.99(13) . . . . ? C13 B1 N19 C23 31.70(17) . . . . ? C7 B1 N19 N20 80.91(12) . . . . ? C1 B1 N19 N20 -41.98(13) . . . . ? C13 B1 N19 N20 -162.28(10) . . . . ? C22 C21 N20 N19 0.49(15) . . . . ? C23 N19 N20 C21 -0.29(14) . . . . ? B1 N19 N20 C21 -169.75(10) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.208 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.030 #===END