# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'James Hoefelmeyer' _publ_contact_author_email James.Hoefelmeyer@usd.edu loop_ _publ_author_name J.Hoefelmeyer 'Jung Son' data_1 _database_code_depnum_ccdc_archive 'CCDC 871057' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 B N' _chemical_formula_weight 161.05 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 ? _symmetry_space_group_name_H-M ? 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 30.181(3) _cell_length_b 9.9266(8) _cell_length_c 14.6281(12) _cell_angle_alpha 90.00 _cell_angle_beta 118.99 _cell_angle_gamma 90.00 _cell_volume 3833.4(5) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.116 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9607 _exptl_absorpt_correction_T_max 0.9838 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 18815 _diffrn_reflns_av_R_equivalents 0.0634 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.42 _reflns_number_total 3529 _reflns_number_gt 3103 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0481P)^2^+2.5177P] 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 3529 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.1010 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 C2 C 0.06160(5) 0.92768(12) -0.03821(10) 0.0253(3) Uani 1 1 d . . . H2 H 0.0780 1.0128 -0.0194 0.030 Uiso 1 1 calc R . . C3 C 0.01203(5) 0.92399(13) -0.11509(11) 0.0314(3) Uani 1 1 d . . . H3 H -0.0054 1.0044 -0.1484 0.038 Uiso 1 1 calc R . . C4 C -0.01216(5) 0.80041(14) -0.14324(11) 0.0311(3) Uani 1 1 d . . . H4 H -0.0464 0.7940 -0.1970 0.037 Uiso 1 1 calc R . . C5 C 0.01434(5) 0.68754(13) -0.09189(10) 0.0256(3) Uani 1 1 d . . . H5 H -0.0020 0.6023 -0.1101 0.031 Uiso 1 1 calc R . . C6 C 0.06505(4) 0.69483(12) -0.01303(9) 0.0190(3) Uani 1 1 d . . . C7 C 0.09271(4) 0.56904(12) 0.03669(9) 0.0193(3) Uani 1 1 d . . . H7A H 0.0694 0.5066 0.0453 0.023 Uiso 1 1 calc R . . H7B H 0.1208 0.5906 0.1072 0.023 Uiso 1 1 calc R . . C8 C 0.16343(5) 0.39099(12) 0.04216(9) 0.0211(3) Uani 1 1 d . . . H8A H 0.1831 0.4335 0.1117 0.025 Uiso 1 1 calc R . . H8B H 0.1491 0.3060 0.0520 0.025 Uiso 1 1 calc R . . C9 C 0.19994(5) 0.35635(15) 0.00074(11) 0.0343(3) Uani 1 1 d . . . H9A H 0.1808 0.3205 -0.0704 0.051 Uiso 1 1 calc R . . H9B H 0.2243 0.2886 0.0461 0.051 Uiso 1 1 calc R . . H9C H 0.2181 0.4378 0.0000 0.051 Uiso 1 1 calc R . . C10 C 0.07172(5) 0.40770(12) -0.12903(10) 0.0248(3) Uani 1 1 d . . . H10A H 0.0476 0.4731 -0.1800 0.030 Uiso 1 1 calc R . . H10B H 0.0871 0.3563 -0.1647 0.030 Uiso 1 1 calc R . . C11 C 0.04210(6) 0.30958(14) -0.09760(12) 0.0345(3) Uani 1 1 d . . . H11A H 0.0658 0.2593 -0.0352 0.052 Uiso 1 1 calc R . . H11B H 0.0230 0.2465 -0.1550 0.052 Uiso 1 1 calc R . . H11C H 0.0185 0.3603 -0.0825 0.052 Uiso 1 1 calc R . . C12 C 0.12775(5) 0.59569(13) -0.18184(9) 0.0232(3) Uani 1 1 d . . . H12 H 0.1065 0.5235 -0.2218 0.028 Uiso 1 1 calc R . . C13 C 0.14531(5) 0.68245(14) -0.22989(10) 0.0271(3) Uani 1 1 d . . . H13 H 0.1364 0.6704 -0.3012 0.033 Uiso 1 1 calc R . . C14 C 0.17635(5) 0.78820(14) -0.17237(10) 0.0275(3) Uani 1 1 d . . . H14 H 0.1888 0.8510 -0.2036 0.033 Uiso 1 1 calc R . . C15 C 0.18868(5) 0.79987(12) -0.06948(10) 0.0234(3) Uani 1 1 d . . . H15 H 0.2100 0.8716 -0.0291 0.028 Uiso 1 1 calc R . . C16 C 0.17054(4) 0.70839(11) -0.02209(9) 0.0184(3) Uani 1 1 d . . . C17 C 0.18449(4) 0.72670(12) 0.08894(9) 0.0184(3) Uani 1 1 d . . . H17A H 0.2203 0.7562 0.1283 0.022 Uiso 1 1 calc R . . H17B H 0.1818 0.6389 0.1180 0.022 Uiso 1 1 calc R . . C18 C 0.15014(5) 0.81731(12) 0.21919(9) 0.0220(3) Uani 1 1 d . . . H18A H 0.1487 0.7194 0.2305 0.026 Uiso 1 1 calc R . . H18B H 0.1831 0.8508 0.2749 0.026 Uiso 1 1 calc R . . C19 C 0.10800(5) 0.88633(13) 0.23156(11) 0.0287(3) Uani 1 1 d . . . H19A H 0.1055 0.9809 0.2104 0.043 Uiso 1 1 calc R . . H19B H 0.1158 0.8814 0.3048 0.043 Uiso 1 1 calc R . . H19C H 0.0757 0.8408 0.1874 0.043 Uiso 1 1 calc R . . C20 C 0.16577(4) 0.99232(12) 0.09695(9) 0.0212(3) Uani 1 1 d . . . H20A H 0.1577 1.0079 0.0236 0.025 Uiso 1 1 calc R . . H20B H 0.1456 1.0571 0.1133 0.025 Uiso 1 1 calc R . . C21 C 0.22230(5) 1.02189(13) 0.16864(10) 0.0262(3) Uani 1 1 d . . . H21A H 0.2326 0.9882 0.2391 0.039 Uiso 1 1 calc R . . H21B H 0.2281 1.1193 0.1715 0.039 Uiso 1 1 calc R . . H21C H 0.2423 0.9770 0.1411 0.039 Uiso 1 1 calc R . . B1 B 0.11654(5) 0.49112(13) -0.03156(10) 0.0191(3) Uani 1 1 d . . . B2 B 0.14825(5) 0.83909(13) 0.10682(10) 0.0185(3) Uani 1 1 d . . . N1 N 0.08863(4) 0.81687(10) 0.01274(8) 0.0187(2) Uani 1 1 d . . . N2 N 0.13896(4) 0.60708(10) -0.08030(7) 0.0177(2) 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 C2 0.0206(6) 0.0168(6) 0.0308(7) -0.0005(5) 0.0065(5) 0.0022(5) C3 0.0214(7) 0.0226(7) 0.0378(8) 0.0025(6) 0.0046(6) 0.0068(5) C4 0.0154(6) 0.0302(7) 0.0365(7) -0.0024(6) 0.0037(6) 0.0024(5) C5 0.0187(6) 0.0221(6) 0.0335(7) -0.0041(5) 0.0108(5) -0.0025(5) C6 0.0181(6) 0.0190(6) 0.0228(6) -0.0018(5) 0.0122(5) 0.0004(4) C7 0.0194(6) 0.0164(6) 0.0228(6) 0.0004(4) 0.0109(5) -0.0007(5) C8 0.0253(6) 0.0175(6) 0.0206(6) 0.0015(5) 0.0111(5) 0.0033(5) C9 0.0347(8) 0.0392(8) 0.0331(7) 0.0133(6) 0.0196(6) 0.0201(6) C10 0.0258(7) 0.0194(6) 0.0253(6) -0.0018(5) 0.0092(5) 0.0008(5) C11 0.0354(8) 0.0231(7) 0.0377(8) -0.0038(6) 0.0120(6) -0.0086(6) C12 0.0234(6) 0.0242(6) 0.0199(6) 0.0013(5) 0.0089(5) 0.0075(5) C13 0.0279(7) 0.0349(7) 0.0199(6) 0.0063(5) 0.0127(5) 0.0108(6) C14 0.0240(6) 0.0327(7) 0.0308(7) 0.0129(5) 0.0172(6) 0.0085(5) C15 0.0183(6) 0.0231(7) 0.0288(7) 0.0050(5) 0.0115(5) 0.0029(5) C16 0.0139(5) 0.0182(6) 0.0225(6) 0.0038(5) 0.0083(5) 0.0067(4) C17 0.0143(5) 0.0178(6) 0.0199(6) 0.0015(4) 0.0058(5) 0.0014(4) C18 0.0229(6) 0.0192(6) 0.0224(6) -0.0014(5) 0.0097(5) 0.0004(5) C19 0.0331(7) 0.0232(7) 0.0365(7) -0.0016(5) 0.0222(6) 0.0000(5) C20 0.0200(6) 0.0188(6) 0.0206(6) -0.0005(5) 0.0064(5) 0.0009(5) C21 0.0229(6) 0.0228(7) 0.0276(6) -0.0031(5) 0.0081(5) -0.0039(5) B1 0.0217(7) 0.0152(6) 0.0214(6) 0.0009(5) 0.0111(6) 0.0009(5) B2 0.0148(6) 0.0178(7) 0.0186(6) -0.0009(5) 0.0048(5) 0.0015(5) N1 0.0166(5) 0.0169(5) 0.0209(5) -0.0007(4) 0.0077(4) 0.0018(4) N2 0.0172(5) 0.0169(5) 0.0184(5) 0.0025(4) 0.0080(4) 0.0055(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 C2 N1 1.3571(15) . ? C2 C3 1.3686(18) . ? C2 H2 0.9500 . ? C3 C4 1.3842(19) . ? C3 H3 0.9500 . ? C4 C5 1.3701(19) . ? C4 H4 0.9500 . ? C5 C6 1.4025(17) . ? C5 H5 0.9500 . ? C6 N1 1.3624(15) . ? C6 C7 1.4820(16) . ? C7 B1 1.6758(17) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.5321(17) . ? C8 B1 1.6353(17) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.5355(19) . ? C10 B1 1.6367(18) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 N2 1.3589(15) . ? C12 C13 1.3702(18) . ? C12 H12 0.9500 . ? C13 C14 1.387(2) . ? C13 H13 0.9500 . ? C14 C15 1.3691(18) . ? C14 H14 0.9500 . ? C15 C16 1.4046(17) . ? C15 H15 0.9500 . ? C16 N2 1.3631(15) . ? C16 C17 1.4783(16) . ? C17 B2 1.6694(17) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.5305(17) . ? C18 B2 1.6314(17) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.5372(16) . ? C20 B2 1.6395(18) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? B1 N2 1.6609(16) . ? B2 N1 1.6675(15) . ? 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 N1 C2 C3 123.80(11) . . ? N1 C2 H2 118.1 . . ? C3 C2 H2 118.1 . . ? C2 C3 C4 118.49(12) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 118.56(12) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C6 121.54(12) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? N1 C6 C5 119.27(11) . . ? N1 C6 C7 121.26(10) . . ? C5 C6 C7 119.39(10) . . ? C6 C7 B1 113.50(9) . . ? C6 C7 H7A 108.9 . . ? B1 C7 H7A 108.9 . . ? C6 C7 H7B 108.9 . . ? B1 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C9 C8 B1 115.72(10) . . ? C9 C8 H8A 108.3 . . ? B1 C8 H8A 108.3 . . ? C9 C8 H8B 108.3 . . ? B1 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 B1 114.55(10) . . ? C11 C10 H10A 108.6 . . ? B1 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? B1 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 C13 123.72(12) . . ? N2 C12 H12 118.1 . . ? C13 C12 H12 118.1 . . ? C12 C13 C14 118.69(11) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C15 C14 C13 118.34(12) . . ? C15 C14 H14 120.8 . . ? C13 C14 H14 120.8 . . ? C14 C15 C16 121.64(12) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? N2 C16 C15 119.38(11) . . ? N2 C16 C17 121.17(10) . . ? C15 C16 C17 119.41(11) . . ? C16 C17 B2 113.26(9) . . ? C16 C17 H17A 108.9 . . ? B2 C17 H17A 108.9 . . ? C16 C17 H17B 108.9 . . ? B2 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C19 C18 B2 115.76(10) . . ? C19 C18 H18A 108.3 . . ? B2 C18 H18A 108.3 . . ? C19 C18 H18B 108.3 . . ? B2 C18 H18B 108.3 . . ? H18A C18 H18B 107.4 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 B2 114.56(10) . . ? C21 C20 H20A 108.6 . . ? B2 C20 H20A 108.6 . . ? C21 C20 H20B 108.6 . . ? B2 C20 H20B 108.6 . . ? H20A C20 H20B 107.6 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C8 B1 C10 110.65(10) . . ? C8 B1 N2 107.57(9) . . ? C10 B1 N2 108.26(9) . . ? C8 B1 C7 111.82(9) . . ? C10 B1 C7 109.90(10) . . ? N2 B1 C7 108.52(9) . . ? C18 B2 C20 110.89(10) . . ? C18 B2 N1 108.10(9) . . ? C20 B2 N1 108.36(9) . . ? C18 B2 C17 111.33(9) . . ? C20 B2 C17 110.03(10) . . ? N1 B2 C17 108.01(9) . . ? C2 N1 C6 118.32(10) . . ? C2 N1 B2 117.85(9) . . ? C6 N1 B2 123.78(9) . . ? C12 N2 C16 118.18(10) . . ? C12 N2 B1 118.31(10) . . ? C16 N2 B1 123.38(9) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.42 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.299 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.038 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 871058' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common BBN-picoline-dimer _chemical_melting_point ? _chemical_formula_moiety 'C28 H40 B2 N2' _chemical_formula_sum 'C28 H40 B2 N2' _chemical_formula_weight 426.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6278(7) _cell_length_b 11.1348(8) _cell_length_c 13.2544(10) _cell_angle_alpha 71.1230(10) _cell_angle_beta 89.2950(10) _cell_angle_gamma 87.4330(10) _cell_volume 1203.64(16) _cell_formula_units_Z 2 _cell_measurement_temperature 247(2) _cell_measurement_reflns_used 3318 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 24.89 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.176 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9771 _exptl_absorpt_correction_T_max 0.9804 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 247(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12312 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.40 _reflns_number_total 4432 _reflns_number_gt 2555 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+0.0969P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4432 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1029 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1372 _refine_ls_wR_factor_gt 0.1161 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 C2 C -0.0512(3) 0.3666(2) 0.67158(18) 0.0491(6) Uani 1 1 d . . . H2 H -0.0254 0.4112 0.6006 0.059 Uiso 1 1 calc R . . C3 C -0.1932(3) 0.3930(2) 0.7076(2) 0.0590(7) Uani 1 1 d . . . H3 H -0.2628 0.4534 0.6623 0.071 Uiso 1 1 calc R . . C4 C -0.2326(3) 0.3295(2) 0.8114(2) 0.0574(7) Uani 1 1 d . . . H4 H -0.3314 0.3422 0.8378 0.069 Uiso 1 1 calc R . . C5 C -0.1242(3) 0.2472(2) 0.87527(18) 0.0492(6) Uani 1 1 d . . . H5 H -0.1488 0.2045 0.9469 0.059 Uiso 1 1 calc R . . C6 C 0.0222(2) 0.22507(19) 0.83686(17) 0.0392(5) Uani 1 1 d . . . C7 C 0.1449(2) 0.15737(19) 0.91317(16) 0.0403(5) Uani 1 1 d . . . H7A H 0.2204 0.1163 0.8776 0.048 Uiso 1 1 calc R . . H7B H 0.0990 0.0910 0.9722 0.048 Uiso 1 1 calc R . . C8 C 0.4075(2) 0.20221(19) 1.00656(16) 0.0424(6) Uani 1 1 d . . . H8 H 0.4694 0.1902 0.9469 0.051 Uiso 1 1 calc R . . C9 C 0.3883(3) 0.0704(2) 1.09077(17) 0.0534(6) Uani 1 1 d . . . H9A H 0.3561 0.0121 1.0541 0.064 Uiso 1 1 calc R . . H9B H 0.4900 0.0389 1.1230 0.064 Uiso 1 1 calc R . . C10 C 0.2720(3) 0.0649(2) 1.18086(18) 0.0579(7) Uani 1 1 d . . . H10A H 0.2416 -0.0232 1.2125 0.069 Uiso 1 1 calc R . . H10B H 0.3250 0.0882 1.2363 0.069 Uiso 1 1 calc R . . C11 C 0.1244(3) 0.1501(2) 1.14836(17) 0.0505(6) Uani 1 1 d . . . H11A H 0.0793 0.1636 1.2123 0.061 Uiso 1 1 calc R . . H11B H 0.0492 0.1052 1.1207 0.061 Uiso 1 1 calc R . . C12 C 0.1478(2) 0.28075(19) 1.06402(16) 0.0404(5) Uani 1 1 d . . . H12 H 0.0443 0.3218 1.0405 0.048 Uiso 1 1 calc R . . C13 C 0.2350(3) 0.3651(2) 1.11454(18) 0.0516(6) Uani 1 1 d . . . H13A H 0.2252 0.4531 1.0667 0.062 Uiso 1 1 calc R . . H13B H 0.1834 0.3620 1.1816 0.062 Uiso 1 1 calc R . . C14 C 0.4068(3) 0.3302(2) 1.13765(19) 0.0600(7) Uani 1 1 d . . . H14A H 0.4569 0.4025 1.1484 0.072 Uiso 1 1 calc R . . H14B H 0.4171 0.2586 1.2041 0.072 Uiso 1 1 calc R . . C15 C 0.4913(3) 0.2944(2) 1.04930(19) 0.0551(7) Uani 1 1 d . . . H15A H 0.5934 0.2561 1.0761 0.066 Uiso 1 1 calc R . . H15B H 0.5082 0.3723 0.9899 0.066 Uiso 1 1 calc R . . C16 C 0.1750(2) 0.5005(2) 0.86686(18) 0.0432(6) Uani 1 1 d . . . H16 H 0.1166 0.4947 0.9285 0.052 Uiso 1 1 calc R . . C17 C 0.1841(3) 0.6171(2) 0.79132(19) 0.0510(6) Uani 1 1 d . . . H17 H 0.1337 0.6891 0.8012 0.061 Uiso 1 1 calc R . . C18 C 0.2684(3) 0.6272(2) 0.70051(19) 0.0523(6) Uani 1 1 d . . . H18 H 0.2813 0.7065 0.6483 0.063 Uiso 1 1 calc R . . C19 C 0.3328(2) 0.5188(2) 0.68836(17) 0.0463(6) Uani 1 1 d . . . H19 H 0.3891 0.5242 0.6260 0.056 Uiso 1 1 calc R . . C20 C 0.3181(2) 0.4001(2) 0.76512(16) 0.0376(5) Uani 1 1 d . . . C21 C 0.3626(2) 0.2853(2) 0.73776(16) 0.0403(5) Uani 1 1 d . . . H21A H 0.3879 0.2148 0.8030 0.048 Uiso 1 1 calc R . . H21B H 0.4550 0.3007 0.6924 0.048 Uiso 1 1 calc R . . C22 C 0.2273(3) 0.0974(2) 0.68245(18) 0.0529(6) Uani 1 1 d . . . H22 H 0.2229 0.0459 0.7588 0.063 Uiso 1 1 calc R . . C23 C 0.3859(3) 0.0694(2) 0.6382(2) 0.0728(8) Uani 1 1 d . . . H23A H 0.4671 0.0787 0.6859 0.087 Uiso 1 1 calc R . . H23B H 0.3909 -0.0194 0.6402 0.087 Uiso 1 1 calc R . . C24 C 0.4228(3) 0.1533(3) 0.5244(2) 0.0779(9) Uani 1 1 d . . . H24A H 0.3689 0.1216 0.4741 0.094 Uiso 1 1 calc R . . H24B H 0.5344 0.1451 0.5123 0.094 Uiso 1 1 calc R . . C25 C 0.3766(3) 0.2949(2) 0.50021(18) 0.0594(7) Uani 1 1 d . . . H25A H 0.3754 0.3360 0.4227 0.071 Uiso 1 1 calc R . . H25B H 0.4562 0.3342 0.5297 0.071 Uiso 1 1 calc R . . C26 C 0.2171(2) 0.3210(2) 0.54514(16) 0.0440(6) Uani 1 1 d . . . H26 H 0.2039 0.4133 0.5333 0.053 Uiso 1 1 calc R . . C27 C 0.0889(3) 0.2826(2) 0.48267(18) 0.0601(7) Uani 1 1 d . . . H27A H -0.0081 0.3279 0.4905 0.072 Uiso 1 1 calc R . . H27B H 0.1163 0.3120 0.4069 0.072 Uiso 1 1 calc R . . C28 C 0.0596(5) 0.1446(3) 0.5143(3) 0.1180(14) Uani 1 1 d . . . H28A H -0.0494 0.1366 0.4984 0.142 Uiso 1 1 calc R . . H28B H 0.1226 0.1088 0.4681 0.142 Uiso 1 1 calc R . . C29 C 0.0895(4) 0.0647(3) 0.6251(2) 0.0784(9) Uani 1 1 d . . . H29A H 0.1060 -0.0234 0.6261 0.094 Uiso 1 1 calc R . . H29B H -0.0043 0.0682 0.6667 0.094 Uiso 1 1 calc R . . B1 B 0.2358(3) 0.2576(2) 0.96133(18) 0.0369(6) Uani 1 1 d . . . B2 B 0.2168(3) 0.2464(2) 0.67348(19) 0.0394(6) Uani 1 1 d . . . N1 N 0.05497(19) 0.28059(16) 0.73118(13) 0.0388(4) Uani 1 1 d . . . N2 N 0.24467(18) 0.39265(15) 0.85882(13) 0.0357(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 C2 0.0470(14) 0.0530(15) 0.0427(14) -0.0091(12) -0.0028(11) -0.0013(12) C3 0.0407(14) 0.0709(18) 0.0568(17) -0.0097(14) -0.0022(12) 0.0040(12) C4 0.0358(14) 0.0762(18) 0.0619(17) -0.0244(15) 0.0038(13) -0.0069(13) C5 0.0428(14) 0.0634(16) 0.0430(14) -0.0182(12) 0.0083(11) -0.0130(12) C6 0.0440(13) 0.0383(12) 0.0397(13) -0.0172(10) 0.0034(11) -0.0128(10) C7 0.0466(13) 0.0387(13) 0.0349(12) -0.0109(10) 0.0059(10) -0.0048(10) C8 0.0447(13) 0.0482(14) 0.0342(12) -0.0141(11) 0.0017(10) 0.0058(11) C9 0.0572(15) 0.0539(15) 0.0454(14) -0.0128(12) -0.0028(12) 0.0129(12) C10 0.0708(17) 0.0492(15) 0.0454(14) -0.0055(12) 0.0050(13) 0.0085(13) C11 0.0560(15) 0.0548(15) 0.0374(13) -0.0112(11) 0.0099(11) 0.0024(12) C12 0.0407(13) 0.0450(13) 0.0344(12) -0.0121(10) 0.0014(10) 0.0023(10) C13 0.0572(15) 0.0603(16) 0.0415(13) -0.0231(12) 0.0003(11) 0.0036(12) C14 0.0584(16) 0.0736(18) 0.0558(16) -0.0316(14) -0.0066(13) -0.0026(13) C15 0.0443(14) 0.0698(17) 0.0547(15) -0.0250(13) -0.0038(12) 0.0004(12) C16 0.0437(13) 0.0406(14) 0.0462(14) -0.0159(11) 0.0015(11) 0.0028(10) C17 0.0531(15) 0.0388(14) 0.0585(16) -0.0128(12) 0.0002(12) 0.0029(11) C18 0.0598(16) 0.0406(14) 0.0505(15) -0.0051(12) -0.0004(12) -0.0122(12) C19 0.0474(14) 0.0527(16) 0.0397(13) -0.0146(12) 0.0060(11) -0.0157(11) C20 0.0316(12) 0.0455(13) 0.0370(13) -0.0140(11) -0.0010(10) -0.0085(10) C21 0.0387(12) 0.0474(13) 0.0363(12) -0.0159(10) 0.0057(10) -0.0014(10) C22 0.0815(18) 0.0431(14) 0.0356(13) -0.0147(11) 0.0029(12) -0.0053(12) C23 0.107(2) 0.0574(17) 0.0556(17) -0.0239(14) 0.0076(16) 0.0226(15) C24 0.093(2) 0.080(2) 0.0615(18) -0.0260(16) 0.0227(16) 0.0167(16) C25 0.0716(18) 0.0670(18) 0.0387(14) -0.0161(13) 0.0140(13) -0.0057(14) C26 0.0532(14) 0.0424(13) 0.0378(13) -0.0145(11) 0.0005(11) -0.0058(11) C27 0.0777(18) 0.0655(18) 0.0390(14) -0.0181(13) -0.0044(13) -0.0120(14) C28 0.170(4) 0.077(2) 0.099(3) -0.012(2) -0.056(3) -0.043(2) C29 0.122(3) 0.0626(19) 0.0572(18) -0.0242(15) 0.0024(17) -0.0359(17) B1 0.0408(14) 0.0357(14) 0.0335(14) -0.0103(11) 0.0033(11) -0.0013(11) B2 0.0425(15) 0.0411(15) 0.0362(14) -0.0146(12) 0.0018(12) -0.0035(12) N1 0.0397(11) 0.0412(11) 0.0370(11) -0.0140(9) -0.0003(8) -0.0078(8) N2 0.0336(10) 0.0373(10) 0.0372(10) -0.0134(8) 0.0004(8) -0.0015(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 C2 N1 1.353(3) . ? C2 C3 1.363(3) . ? C2 H2 0.9400 . ? C3 C4 1.375(3) . ? C3 H3 0.9400 . ? C4 C5 1.368(3) . ? C4 H4 0.9400 . ? C5 C6 1.398(3) . ? C5 H5 0.9400 . ? C6 N1 1.367(2) . ? C6 C7 1.474(3) . ? C7 B1 1.680(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 C15 1.533(3) . ? C8 C9 1.544(3) . ? C8 B1 1.624(3) . ? C8 H8 0.9900 . ? C9 C10 1.538(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C10 C11 1.533(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C11 C12 1.541(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C12 C13 1.543(3) . ? C12 B1 1.637(3) . ? C12 H12 0.9900 . ? C13 C14 1.525(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 C15 1.522(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C16 N2 1.353(2) . ? C16 C17 1.364(3) . ? C16 H16 0.9400 . ? C17 C18 1.374(3) . ? C17 H17 0.9400 . ? C18 C19 1.362(3) . ? C18 H18 0.9400 . ? C19 C20 1.392(3) . ? C19 H19 0.9400 . ? C20 N2 1.367(2) . ? C20 C21 1.472(3) . ? C21 B2 1.676(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C22 C29 1.537(3) . ? C22 C23 1.541(3) . ? C22 B2 1.623(3) . ? C22 H22 0.9900 . ? C23 C24 1.533(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C24 C25 1.538(3) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C25 C26 1.545(3) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C26 C27 1.544(3) . ? C26 B2 1.634(3) . ? C26 H26 0.9900 . ? C27 C28 1.488(4) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C28 C29 1.470(4) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? B1 N2 1.673(3) . ? B2 N1 1.672(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 N1 C2 C3 124.4(2) . . ? N1 C2 H2 117.8 . . ? C3 C2 H2 117.8 . . ? C2 C3 C4 118.6(2) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 118.2(2) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? C4 C5 C6 121.7(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? N1 C6 C5 119.3(2) . . ? N1 C6 C7 120.91(18) . . ? C5 C6 C7 119.2(2) . . ? C6 C7 B1 111.02(17) . . ? C6 C7 H7A 109.4 . . ? B1 C7 H7A 109.4 . . ? C6 C7 H7B 109.4 . . ? B1 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C15 C8 C9 113.37(18) . . ? C15 C8 B1 111.85(17) . . ? C9 C8 B1 107.36(18) . . ? C15 C8 H8 108.0 . . ? C9 C8 H8 108.0 . . ? B1 C8 H8 108.0 . . ? C10 C9 C8 116.26(18) . . ? C10 C9 H9A 108.2 . . ? C8 C9 H9A 108.2 . . ? C10 C9 H9B 108.2 . . ? C8 C9 H9B 108.2 . . ? H9A C9 H9B 107.4 . . ? C11 C10 C9 115.85(18) . . ? C11 C10 H10A 108.3 . . ? C9 C10 H10A 108.3 . . ? C11 C10 H10B 108.3 . . ? C9 C10 H10B 108.3 . . ? H10A C10 H10B 107.4 . . ? C10 C11 C12 115.09(19) . . ? C10 C11 H11A 108.5 . . ? C12 C11 H11A 108.5 . . ? C10 C11 H11B 108.5 . . ? C12 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? C11 C12 C13 109.50(18) . . ? C11 C12 B1 108.16(17) . . ? C13 C12 B1 114.17(18) . . ? C11 C12 H12 108.3 . . ? C13 C12 H12 108.3 . . ? B1 C12 H12 108.3 . . ? C14 C13 C12 115.94(18) . . ? C14 C13 H13A 108.3 . . ? C12 C13 H13A 108.3 . . ? C14 C13 H13B 108.3 . . ? C12 C13 H13B 108.3 . . ? H13A C13 H13B 107.4 . . ? C15 C14 C13 113.52(19) . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? C13 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C14 C15 C8 115.20(19) . . ? C14 C15 H15A 108.5 . . ? C8 C15 H15A 108.5 . . ? C14 C15 H15B 108.5 . . ? C8 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? N2 C16 C17 124.2(2) . . ? N2 C16 H16 117.9 . . ? C17 C16 H16 117.9 . . ? C16 C17 C18 118.6(2) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? C19 C18 C17 118.1(2) . . ? C19 C18 H18 121.0 . . ? C17 C18 H18 121.0 . . ? C18 C19 C20 122.3(2) . . ? C18 C19 H19 118.9 . . ? C20 C19 H19 118.9 . . ? N2 C20 C19 119.03(19) . . ? N2 C20 C21 121.38(18) . . ? C19 C20 C21 119.07(19) . . ? C20 C21 B2 110.12(17) . . ? C20 C21 H21A 109.6 . . ? B2 C21 H21A 109.6 . . ? C20 C21 H21B 109.6 . . ? B2 C21 H21B 109.6 . . ? H21A C21 H21B 108.2 . . ? C29 C22 C23 113.2(2) . . ? C29 C22 B2 110.8(2) . . ? C23 C22 B2 107.97(19) . . ? C29 C22 H22 108.3 . . ? C23 C22 H22 108.3 . . ? B2 C22 H22 108.3 . . ? C24 C23 C22 115.8(2) . . ? C24 C23 H23A 108.3 . . ? C22 C23 H23A 108.3 . . ? C24 C23 H23B 108.3 . . ? C22 C23 H23B 108.3 . . ? H23A C23 H23B 107.4 . . ? C23 C24 C25 114.44(19) . . ? C23 C24 H24A 108.7 . . ? C25 C24 H24A 108.7 . . ? C23 C24 H24B 108.7 . . ? C25 C24 H24B 108.7 . . ? H24A C24 H24B 107.6 . . ? C24 C25 C26 114.6(2) . . ? C24 C25 H25A 108.6 . . ? C26 C25 H25A 108.6 . . ? C24 C25 H25B 108.6 . . ? C26 C25 H25B 108.6 . . ? H25A C25 H25B 107.6 . . ? C27 C26 C25 108.63(18) . . ? C27 C26 B2 114.46(18) . . ? C25 C26 B2 108.43(18) . . ? C27 C26 H26 108.4 . . ? C25 C26 H26 108.4 . . ? B2 C26 H26 108.4 . . ? C28 C27 C26 116.4(2) . . ? C28 C27 H27A 108.2 . . ? C26 C27 H27A 108.2 . . ? C28 C27 H27B 108.2 . . ? C26 C27 H27B 108.2 . . ? H27A C27 H27B 107.4 . . ? C29 C28 C27 118.9(2) . . ? C29 C28 H28A 107.6 . . ? C27 C28 H28A 107.6 . . ? C29 C28 H28B 107.6 . . ? C27 C28 H28B 107.6 . . ? H28A C28 H28B 107.0 . . ? C28 C29 C22 117.2(2) . . ? C28 C29 H29A 108.0 . . ? C22 C29 H29A 108.0 . . ? C28 C29 H29B 108.0 . . ? C22 C29 H29B 108.0 . . ? H29A C29 H29B 107.2 . . ? C8 B1 C12 103.77(17) . . ? C8 B1 N2 111.43(17) . . ? C12 B1 N2 111.60(16) . . ? C8 B1 C7 111.84(17) . . ? C12 B1 C7 113.21(17) . . ? N2 B1 C7 105.17(15) . . ? C22 B2 C26 103.83(17) . . ? C22 B2 N1 110.71(17) . . ? C26 B2 N1 111.82(17) . . ? C22 B2 C21 112.32(18) . . ? C26 B2 C21 113.10(17) . . ? N1 B2 C21 105.22(15) . . ? C2 N1 C6 117.27(18) . . ? C2 N1 B2 119.37(17) . . ? C6 N1 B2 123.35(17) . . ? C16 N2 C20 117.38(18) . . ? C16 N2 B1 119.43(17) . . ? C20 N2 B1 123.18(16) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.240 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.035 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 871059' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common diphenylboronpicoline-dimer _chemical_melting_point ? _chemical_formula_moiety 'C36 H32 B2 N2' _chemical_formula_sum 'C36 H32 B2 N2' _chemical_formula_weight 514.26 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 20.0937(16) _cell_length_b 9.9331(8) _cell_length_c 15.1773(12) _cell_angle_alpha 90.00 _cell_angle_beta 112.8710(10) _cell_angle_gamma 90.00 _cell_volume 2791.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6791 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 25.44 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9647 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details 'SADABS (Bruker,2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13754 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 25.46 _reflns_number_total 2591 _reflns_number_gt 2094 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0374P)^2^+2.3213P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2591 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0907 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 C2 C 0.35403(7) 0.29414(14) 0.19851(10) 0.0206(3) Uani 1 1 d . . . H2 H 0.3397 0.3118 0.2501 0.025 Uiso 1 1 calc R . . C3 C 0.32079(8) 0.36432(14) 0.11505(10) 0.0245(3) Uani 1 1 d . . . H3 H 0.2845 0.4290 0.1092 0.029 Uiso 1 1 calc R . . C4 C 0.34127(7) 0.33893(15) 0.03940(10) 0.0243(3) Uani 1 1 d . . . H4 H 0.3193 0.3857 -0.0195 0.029 Uiso 1 1 calc R . . C5 C 0.39404(7) 0.24462(14) 0.05138(10) 0.0215(3) Uani 1 1 d . . . H5 H 0.4085 0.2267 -0.0001 0.026 Uiso 1 1 calc R . . C6 C 0.42705(7) 0.17425(13) 0.13732(9) 0.0171(3) Uani 1 1 d . . . C7 C 0.48110(7) 0.06842(13) 0.14665(9) 0.0170(3) Uani 1 1 d . . . H7A H 0.4696 0.0303 0.0821 0.020 Uiso 1 1 calc R . . H7B H 0.4735 -0.0044 0.1863 0.020 Uiso 1 1 calc R . . C8 C 0.38473(7) -0.03309(14) 0.27548(9) 0.0182(3) Uani 1 1 d . . . C9 C 0.41271(8) -0.15785(14) 0.31629(10) 0.0225(3) Uani 1 1 d . . . H9 H 0.4612 -0.1623 0.3614 0.027 Uiso 1 1 calc R . . C10 C 0.37195(8) -0.27529(15) 0.29311(11) 0.0266(3) Uani 1 1 d . . . H10 H 0.3927 -0.3579 0.3226 0.032 Uiso 1 1 calc R . . C11 C 0.30110(8) -0.27232(15) 0.22708(11) 0.0262(3) Uani 1 1 d . . . H11 H 0.2731 -0.3524 0.2110 0.031 Uiso 1 1 calc R . . C12 C 0.27176(8) -0.15073(15) 0.18489(10) 0.0244(3) Uani 1 1 d . . . H12 H 0.2234 -0.1473 0.1392 0.029 Uiso 1 1 calc R . . C13 C 0.31291(7) -0.03412(14) 0.20921(10) 0.0208(3) Uani 1 1 d . . . H13 H 0.2916 0.0482 0.1798 0.025 Uiso 1 1 calc R . . C14 C 0.41325(7) 0.18520(14) 0.39002(9) 0.0189(3) Uani 1 1 d . . . C15 C 0.37624(8) 0.12236(15) 0.44013(10) 0.0230(3) Uani 1 1 d . . . H15 H 0.3573 0.0345 0.4214 0.028 Uiso 1 1 calc R . . C16 C 0.36618(9) 0.18431(16) 0.51656(11) 0.0303(4) Uani 1 1 d . . . H16 H 0.3408 0.1385 0.5488 0.036 Uiso 1 1 calc R . . C17 C 0.39294(9) 0.31179(17) 0.54541(11) 0.0319(4) Uani 1 1 d . . . H17 H 0.3865 0.3538 0.5978 0.038 Uiso 1 1 calc R . . C18 C 0.42932(8) 0.37787(16) 0.49724(11) 0.0295(4) Uani 1 1 d . . . H18 H 0.4477 0.4660 0.5162 0.035 Uiso 1 1 calc R . . C19 C 0.43905(7) 0.31539(15) 0.42112(10) 0.0238(3) Uani 1 1 d . . . H19 H 0.4641 0.3625 0.3889 0.029 Uiso 1 1 calc R . . B1 B 0.43123(8) 0.10560(15) 0.30782(11) 0.0171(3) Uani 1 1 d . . . N1 N 0.40644(6) 0.20065(11) 0.21139(8) 0.0166(3) 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 C2 0.0170(7) 0.0219(7) 0.0239(7) 0.0004(6) 0.0091(6) 0.0014(6) C3 0.0197(7) 0.0240(8) 0.0287(8) 0.0042(6) 0.0082(6) 0.0041(6) C4 0.0200(7) 0.0267(8) 0.0220(7) 0.0074(6) 0.0035(6) -0.0011(6) C5 0.0199(7) 0.0272(8) 0.0174(7) 0.0017(6) 0.0071(6) -0.0032(6) C6 0.0140(6) 0.0201(7) 0.0164(7) -0.0014(5) 0.0052(5) -0.0053(5) C7 0.0171(7) 0.0199(7) 0.0143(6) -0.0017(5) 0.0064(5) -0.0019(5) C8 0.0190(7) 0.0229(7) 0.0170(7) -0.0007(6) 0.0117(6) -0.0001(6) C9 0.0210(7) 0.0247(8) 0.0229(7) 0.0014(6) 0.0098(6) -0.0007(6) C10 0.0320(8) 0.0219(8) 0.0300(8) 0.0010(6) 0.0165(7) 0.0000(6) C11 0.0292(8) 0.0252(8) 0.0307(8) -0.0069(6) 0.0186(7) -0.0095(6) C12 0.0186(7) 0.0330(8) 0.0237(8) -0.0052(6) 0.0105(6) -0.0048(6) C13 0.0193(7) 0.0252(8) 0.0204(7) -0.0002(6) 0.0103(6) 0.0002(6) C14 0.0143(7) 0.0245(7) 0.0163(7) 0.0035(6) 0.0044(5) 0.0060(6) C15 0.0230(7) 0.0255(8) 0.0223(7) 0.0075(6) 0.0108(6) 0.0087(6) C16 0.0343(9) 0.0383(9) 0.0250(8) 0.0134(7) 0.0189(7) 0.0176(7) C17 0.0338(9) 0.0430(10) 0.0199(8) -0.0012(7) 0.0116(7) 0.0171(7) C18 0.0232(8) 0.0335(9) 0.0290(8) -0.0095(7) 0.0071(7) 0.0053(6) C19 0.0180(7) 0.0284(8) 0.0247(8) -0.0030(6) 0.0081(6) 0.0018(6) B1 0.0152(7) 0.0207(8) 0.0155(7) 0.0023(6) 0.0061(6) 0.0001(6) N1 0.0135(6) 0.0180(6) 0.0182(6) 0.0001(5) 0.0059(5) -0.0014(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 C2 N1 1.3600(17) . ? C2 C3 1.371(2) . ? C2 H2 0.9500 . ? C3 C4 1.385(2) . ? C3 H3 0.9500 . ? C4 C5 1.373(2) . ? C4 H4 0.9500 . ? C5 C6 1.3990(19) . ? C5 H5 0.9500 . ? C6 N1 1.3661(17) . ? C6 C7 1.4782(18) . ? C7 B1 1.6647(19) 2_655 ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.4017(19) . ? C8 C13 1.4022(19) . ? C8 B1 1.629(2) . ? C9 C10 1.390(2) . ? C9 H9 0.9500 . ? C10 C11 1.387(2) . ? C10 H10 0.9500 . ? C11 C12 1.387(2) . ? C11 H11 0.9500 . ? C12 C13 1.387(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.4001(19) . ? C14 C19 1.405(2) . ? C14 B1 1.632(2) . ? C15 C16 1.396(2) . ? C15 H15 0.9500 . ? C16 C17 1.379(2) . ? C16 H16 0.9500 . ? C17 C18 1.384(2) . ? C17 H17 0.9500 . ? C18 C19 1.391(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? B1 N1 1.6475(18) . ? B1 C7 1.6647(19) 2_655 ? 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 N1 C2 C3 123.51(13) . . ? N1 C2 H2 118.2 . . ? C3 C2 H2 118.2 . . ? C2 C3 C4 118.59(13) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 118.52(13) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C6 121.75(13) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? N1 C6 C5 119.07(12) . . ? N1 C6 C7 120.28(11) . . ? C5 C6 C7 120.60(12) . . ? C6 C7 B1 120.11(11) . 2_655 ? C6 C7 H7A 107.3 . . ? B1 C7 H7A 107.3 2_655 . ? C6 C7 H7B 107.3 . . ? B1 C7 H7B 107.3 2_655 . ? H7A C7 H7B 106.9 . . ? C9 C8 C13 115.76(12) . . ? C9 C8 B1 122.00(12) . . ? C13 C8 B1 122.14(12) . . ? C10 C9 C8 122.32(13) . . ? C10 C9 H9 118.8 . . ? C8 C9 H9 118.8 . . ? C11 C10 C9 120.23(14) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C10 119.02(13) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C13 120.13(13) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C8 122.53(13) . . ? C12 C13 H13 118.7 . . ? C8 C13 H13 118.7 . . ? C15 C14 C19 115.62(13) . . ? C15 C14 B1 121.43(12) . . ? C19 C14 B1 122.71(12) . . ? C16 C15 C14 122.28(14) . . ? C16 C15 H15 118.9 . . ? C14 C15 H15 118.9 . . ? C17 C16 C15 120.28(14) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.26(14) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C17 C18 C19 120.06(15) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C18 C19 C14 122.49(14) . . ? C18 C19 H19 118.8 . . ? C14 C19 H19 118.8 . . ? C8 B1 C14 111.63(11) . . ? C8 B1 N1 106.07(10) . . ? C14 B1 N1 108.73(11) . . ? C8 B1 C7 109.14(11) . 2_655 ? C14 B1 C7 107.64(11) . 2_655 ? N1 B1 C7 113.69(10) . 2_655 ? C2 N1 C6 118.57(11) . . ? C2 N1 B1 117.96(11) . . ? C6 N1 B1 122.50(11) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.46 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.270 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.037 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 871060' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common borafluorenylpicoline-CH3CN-solvate _chemical_melting_point ? _chemical_formula_moiety 'C36 H23 B2 N2, C2 H3 N' _chemical_formula_sum 'C38 H26 B2 N3' _chemical_formula_weight 546.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 19.7442(8) _cell_length_b 8.9337(4) _cell_length_c 16.7141(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.4670(10) _cell_angle_gamma 90.00 _cell_volume 2867.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9946 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 25.30 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1140 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9654 _exptl_absorpt_correction_T_max 0.9858 _exptl_absorpt_process_details 'SADABS (Bruker,2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27952 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.31 _reflns_number_total 5218 _reflns_number_gt 4216 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0895P)^2^+2.0983P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5218 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1596 _refine_ls_wR_factor_gt 0.1483 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 C2 C 0.18834(11) 0.2633(2) 0.22403(13) 0.0209(5) Uani 1 1 d . . . C3 C 0.18853(12) 0.4157(2) 0.21078(14) 0.0261(5) Uani 1 1 d . . . C4 C 0.20645(12) 0.5095(3) 0.27883(15) 0.0304(5) Uani 1 1 d . . . C5 C 0.22372(11) 0.4470(2) 0.35651(14) 0.0266(5) Uani 1 1 d . . . C6 C 0.22386(10) 0.2909(2) 0.36776(13) 0.0191(4) Uani 1 1 d . . . C7 C 0.24486(10) 0.2281(2) 0.45251(12) 0.0188(4) Uani 1 1 d . . . H7A H 0.2178 0.1355 0.4546 0.023 Uiso 1 1 calc R . . H7B H 0.2319 0.3008 0.4911 0.023 Uiso 1 1 calc R . . C8 C 0.34504(10) 0.1010(2) 0.57272(12) 0.0168(4) Uani 1 1 d . . . C9 C 0.33264(10) -0.0454(2) 0.59449(13) 0.0200(4) Uani 1 1 d . . . C10 C 0.35529(11) -0.0930(2) 0.67590(13) 0.0223(5) Uani 1 1 d . . . H10 H 0.3472 -0.1933 0.6900 0.027 Uiso 1 1 calc R . . C11 C 0.38954(11) 0.0049(2) 0.73652(13) 0.0224(5) Uani 1 1 d . . . H11 H 0.4042 -0.0284 0.7918 0.027 Uiso 1 1 calc R . . C12 C 0.40234(11) 0.1512(2) 0.71645(12) 0.0204(5) Uani 1 1 d . . . H12 H 0.4251 0.2189 0.7579 0.025 Uiso 1 1 calc R . . C13 C 0.38156(10) 0.1978(2) 0.63505(12) 0.0169(4) Uani 1 1 d . . . C14 C 0.39651(10) 0.3419(2) 0.59932(12) 0.0170(4) Uani 1 1 d . . . C15 C 0.43108(11) 0.4650(2) 0.64102(13) 0.0209(5) Uani 1 1 d . . . H15 H 0.4473 0.4629 0.6992 0.025 Uiso 1 1 calc R . . C16 C 0.44162(11) 0.5902(2) 0.59703(13) 0.0230(5) Uani 1 1 d . . . H16 H 0.4647 0.6749 0.6252 0.028 Uiso 1 1 calc R . . C17 C 0.41873(11) 0.5932(2) 0.51202(14) 0.0240(5) Uani 1 1 d . . . H17 H 0.4264 0.6794 0.4821 0.029 Uiso 1 1 calc R . . C18 C 0.38443(11) 0.4696(2) 0.47065(13) 0.0208(5) Uani 1 1 d . . . H18 H 0.3692 0.4724 0.4124 0.025 Uiso 1 1 calc R . . C19 C 0.37202(10) 0.3417(2) 0.51300(12) 0.0167(4) Uani 1 1 d . . . C20 C 0.43020(10) 0.1141(2) 0.42319(12) 0.0181(4) Uani 1 1 d . . . H20 H 0.4521 0.1998 0.4516 0.022 Uiso 1 1 calc R . . C21 C 0.46889(11) 0.0220(2) 0.38525(12) 0.0198(4) Uani 1 1 d . . . H21 H 0.5163 0.0438 0.3872 0.024 Uiso 1 1 calc R . . C22 C 0.43709(11) -0.1035(2) 0.34402(12) 0.0205(5) Uani 1 1 d . . . H22 H 0.4625 -0.1705 0.3179 0.025 Uiso 1 1 calc R . . C23 C 0.36807(11) -0.1288(2) 0.34179(12) 0.0190(4) Uani 1 1 d . . . H23 H 0.3455 -0.2132 0.3127 0.023 Uiso 1 1 calc R . . C24 C 0.33012(10) -0.0332(2) 0.38127(11) 0.0155(4) Uani 1 1 d . . . C25 C 0.25602(10) -0.0656(2) 0.37763(12) 0.0169(4) Uani 1 1 d . . . H25A H 0.2461 -0.0367 0.4309 0.020 Uiso 1 1 calc R . . H25B H 0.2489 -0.1751 0.3714 0.020 Uiso 1 1 calc R . . C26 C 0.12171(10) -0.0374(2) 0.31066(13) 0.0197(5) Uani 1 1 d . . . C27 C 0.08446(11) -0.0187(3) 0.37086(14) 0.0256(5) Uani 1 1 d . . . H27 H 0.1010 0.0490 0.4149 0.031 Uiso 1 1 calc R . . C28 C 0.02299(12) -0.0982(3) 0.36742(16) 0.0334(6) Uani 1 1 d . . . H28 H -0.0025 -0.0830 0.4084 0.040 Uiso 1 1 calc R . . C29 C -0.00090(12) -0.1996(3) 0.30420(18) 0.0381(6) Uani 1 1 d . . . H29 H -0.0424 -0.2544 0.3026 0.046 Uiso 1 1 calc R . . C30 C 0.03546(12) -0.2214(3) 0.24334(16) 0.0324(6) Uani 1 1 d . . . H30 H 0.0194 -0.2915 0.2004 0.039 Uiso 1 1 calc R . . C31 C 0.09581(11) -0.1390(2) 0.24617(14) 0.0236(5) Uani 1 1 d . . . C32 C 0.14129(11) -0.1450(2) 0.18723(13) 0.0224(5) Uani 1 1 d . . . C33 C 0.13119(12) -0.2236(2) 0.11341(14) 0.0293(5) Uani 1 1 d . . . H33 H 0.0914 -0.2855 0.0960 0.035 Uiso 1 1 calc R . . C34 C 0.17949(13) -0.2110(3) 0.06562(14) 0.0328(6) Uani 1 1 d . . . H34 H 0.1728 -0.2646 0.0153 0.039 Uiso 1 1 calc R . . C35 C 0.23764(13) -0.1203(3) 0.09092(13) 0.0284(5) Uani 1 1 d . . . H35 H 0.2702 -0.1109 0.0574 0.034 Uiso 1 1 calc R . . C36 C 0.24835(11) -0.0432(2) 0.16526(13) 0.0224(5) Uani 1 1 d . . . H36 H 0.2887 0.0173 0.1825 0.027 Uiso 1 1 calc R . . C37 C 0.20054(11) -0.0537(2) 0.21468(12) 0.0191(4) Uani 1 1 d . . . B1 B 0.32847(11) 0.1884(3) 0.48527(14) 0.0163(5) Uani 1 1 d . . . B2 B 0.19835(12) 0.0188(2) 0.30288(14) 0.0173(5) Uani 1 1 d . . . N1 N 0.20633(8) 0.20004(18) 0.30046(10) 0.0168(4) Uani 1 1 d . . . N2 N 0.36205(8) 0.08866(18) 0.42214(10) 0.0155(4) Uani 1 1 d . . . C38 C 0.05560(15) 0.0077(3) 0.91950(17) 0.0439(7) Uani 1 1 d . . . H38A H 0.0794 0.0234 0.8749 0.066 Uiso 1 1 calc R . . H38B H 0.0051 0.0103 0.8972 0.066 Uiso 1 1 calc R . . H38C H 0.0689 -0.0899 0.9451 0.066 Uiso 1 1 calc R . . C39 C 0.07556(13) 0.1258(3) 0.98110(16) 0.0336(6) Uani 1 1 d . . . N3 N 0.09125(12) 0.2165(3) 1.02809(15) 0.0471(6) 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 C2 0.0185(10) 0.0206(11) 0.0225(11) 0.0040(9) 0.0027(8) 0.0015(8) C3 0.0248(11) 0.0203(11) 0.0302(12) 0.0034(9) 0.0003(9) 0.0007(9) C4 0.0296(13) 0.0193(11) 0.0358(13) 0.0017(10) -0.0056(10) 0.0005(9) C5 0.0237(11) 0.0200(11) 0.0316(13) -0.0011(9) -0.0024(9) 0.0039(9) C6 0.0135(10) 0.0186(10) 0.0233(11) -0.0032(8) 0.0002(8) 0.0022(8) C7 0.0185(10) 0.0187(10) 0.0188(10) -0.0045(8) 0.0034(8) 0.0009(8) C8 0.0142(10) 0.0194(10) 0.0174(10) -0.0011(8) 0.0052(8) 0.0007(8) C9 0.0189(10) 0.0218(11) 0.0200(11) 0.0016(8) 0.0062(8) -0.0020(8) C10 0.0250(11) 0.0212(11) 0.0214(11) 0.0043(9) 0.0067(9) -0.0025(9) C11 0.0244(11) 0.0278(11) 0.0150(10) 0.0037(9) 0.0044(8) -0.0011(9) C12 0.0212(11) 0.0238(11) 0.0159(10) -0.0031(8) 0.0035(8) -0.0011(8) C13 0.0151(10) 0.0194(10) 0.0169(10) -0.0023(8) 0.0054(8) 0.0012(8) C14 0.0149(10) 0.0174(10) 0.0193(10) -0.0017(8) 0.0051(8) 0.0013(8) C15 0.0203(11) 0.0227(11) 0.0186(10) -0.0036(8) 0.0023(8) -0.0011(9) C16 0.0237(11) 0.0183(11) 0.0261(12) -0.0071(9) 0.0041(9) -0.0050(8) C17 0.0247(11) 0.0179(11) 0.0290(12) 0.0033(9) 0.0058(9) -0.0022(9) C18 0.0222(11) 0.0212(11) 0.0182(10) 0.0018(8) 0.0033(8) 0.0004(8) C19 0.0150(10) 0.0167(10) 0.0183(10) -0.0010(8) 0.0036(8) 0.0010(8) C20 0.0174(10) 0.0189(10) 0.0170(10) 0.0026(8) 0.0018(8) -0.0019(8) C21 0.0169(10) 0.0237(11) 0.0189(10) 0.0052(8) 0.0040(8) 0.0022(8) C22 0.0241(11) 0.0208(11) 0.0177(10) 0.0025(8) 0.0073(8) 0.0065(9) C23 0.0213(11) 0.0184(10) 0.0156(10) -0.0014(8) 0.0009(8) 0.0009(8) C24 0.0187(10) 0.0146(10) 0.0120(9) 0.0032(7) 0.0010(8) 0.0005(8) C25 0.0175(10) 0.0153(10) 0.0166(10) 0.0002(8) 0.0017(8) -0.0009(8) C26 0.0158(10) 0.0165(10) 0.0243(11) 0.0065(8) -0.0006(8) 0.0020(8) C27 0.0194(11) 0.0245(12) 0.0323(12) 0.0063(9) 0.0050(9) 0.0032(9) C28 0.0212(12) 0.0335(13) 0.0474(15) 0.0142(11) 0.0117(11) 0.0044(10) C29 0.0190(12) 0.0318(13) 0.0602(18) 0.0124(12) 0.0022(11) -0.0070(10) C30 0.0238(12) 0.0235(12) 0.0429(14) 0.0038(10) -0.0065(10) -0.0055(9) C31 0.0198(11) 0.0170(10) 0.0286(12) 0.0049(9) -0.0050(9) 0.0011(8) C32 0.0240(11) 0.0150(10) 0.0223(11) 0.0029(8) -0.0066(9) 0.0031(8) C33 0.0328(13) 0.0182(11) 0.0288(12) -0.0038(9) -0.0097(10) 0.0043(9) C34 0.0440(15) 0.0272(13) 0.0212(12) -0.0054(10) -0.0048(10) 0.0149(11) C35 0.0364(13) 0.0283(12) 0.0193(11) 0.0032(9) 0.0041(10) 0.0147(10) C36 0.0263(11) 0.0200(11) 0.0196(11) 0.0029(8) 0.0030(9) 0.0061(9) C37 0.0215(11) 0.0141(10) 0.0184(10) 0.0019(8) -0.0019(8) 0.0033(8) B1 0.0162(11) 0.0168(11) 0.0150(11) -0.0013(9) 0.0021(9) -0.0008(9) B2 0.0168(11) 0.0132(11) 0.0203(12) 0.0002(9) 0.0010(9) -0.0006(9) N1 0.0140(8) 0.0158(9) 0.0196(9) 0.0001(7) 0.0018(7) -0.0003(6) N2 0.0173(9) 0.0156(8) 0.0132(8) 0.0011(7) 0.0024(7) 0.0003(7) C38 0.0426(16) 0.0434(16) 0.0413(16) 0.0040(13) 0.0009(12) 0.0030(13) C39 0.0282(13) 0.0372(14) 0.0340(14) 0.0085(12) 0.0046(11) -0.0009(11) N3 0.0428(14) 0.0572(16) 0.0441(14) -0.0004(13) 0.0158(11) -0.0004(12) _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 C2 N1 1.366(3) . ? C2 C3 1.380(3) . ? C3 C4 1.391(3) . ? C4 C5 1.381(3) . ? C5 C6 1.407(3) . ? C6 N1 1.365(3) . ? C6 C7 1.490(3) . ? C7 B1 1.652(3) . ? C8 C9 1.395(3) . ? C8 C13 1.415(3) . ? C8 B1 1.622(3) . ? C9 C10 1.396(3) . ? C10 C11 1.389(3) . ? C11 C12 1.387(3) . ? C12 C13 1.390(3) . ? C13 C14 1.478(3) . ? C14 C15 1.392(3) . ? C14 C19 1.411(3) . ? C15 C16 1.381(3) . ? C16 C17 1.387(3) . ? C17 C18 1.392(3) . ? C18 C19 1.396(3) . ? C19 B1 1.626(3) . ? C20 N2 1.361(3) . ? C20 C21 1.374(3) . ? C21 C22 1.388(3) . ? C22 C23 1.373(3) . ? C23 C24 1.398(3) . ? C24 N2 1.360(3) . ? C24 C25 1.479(3) . ? C25 B2 1.662(3) . ? C26 C27 1.388(3) . ? C26 C31 1.411(3) . ? C26 B2 1.628(3) . ? C27 C28 1.396(3) . ? C28 C29 1.388(4) . ? C29 C30 1.389(4) . ? C30 C31 1.392(3) . ? C31 C32 1.481(3) . ? C32 C33 1.393(3) . ? C32 C37 1.412(3) . ? C33 C34 1.384(4) . ? C34 C35 1.388(4) . ? C35 C36 1.393(3) . ? C36 C37 1.395(3) . ? C37 B2 1.620(3) . ? B1 N2 1.635(3) . ? B2 N1 1.628(3) . ? C38 C39 1.463(4) . ? C39 N3 1.121(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 N1 C2 C3 123.3(2) . . ? C2 C3 C4 118.2(2) . . ? C5 C4 C3 119.0(2) . . ? C4 C5 C6 121.3(2) . . ? N1 C6 C5 119.14(19) . . ? N1 C6 C7 121.40(18) . . ? C5 C6 C7 119.45(19) . . ? C6 C7 B1 115.54(17) . . ? C9 C8 C13 118.11(18) . . ? C9 C8 B1 132.52(18) . . ? C13 C8 B1 109.31(17) . . ? C8 C9 C10 120.25(19) . . ? C11 C10 C9 120.71(19) . . ? C12 C11 C10 120.12(19) . . ? C11 C12 C13 119.33(19) . . ? C12 C13 C8 121.43(19) . . ? C12 C13 C14 127.96(19) . . ? C8 C13 C14 110.50(17) . . ? C15 C14 C19 121.63(19) . . ? C15 C14 C13 127.33(19) . . ? C19 C14 C13 111.02(17) . . ? C16 C15 C14 119.35(19) . . ? C15 C16 C17 120.5(2) . . ? C16 C17 C18 119.9(2) . . ? C17 C18 C19 121.33(19) . . ? C18 C19 C14 117.29(18) . . ? C18 C19 B1 133.52(18) . . ? C14 C19 B1 108.99(17) . . ? N2 C20 C21 123.24(19) . . ? C20 C21 C22 118.51(19) . . ? C23 C22 C21 118.53(19) . . ? C22 C23 C24 121.63(19) . . ? N2 C24 C23 119.27(18) . . ? N2 C24 C25 121.06(17) . . ? C23 C24 C25 119.67(18) . . ? C24 C25 B2 116.11(16) . . ? C27 C26 C31 118.18(19) . . ? C27 C26 B2 132.86(19) . . ? C31 C26 B2 108.40(18) . . ? C26 C27 C28 120.7(2) . . ? C29 C28 C27 120.1(2) . . ? C28 C29 C30 120.5(2) . . ? C29 C30 C31 119.0(2) . . ? C30 C31 C26 121.4(2) . . ? C30 C31 C32 127.3(2) . . ? C26 C31 C32 111.31(18) . . ? C33 C32 C37 121.0(2) . . ? C33 C32 C31 128.6(2) . . ? C37 C32 C31 110.35(18) . . ? C34 C33 C32 119.7(2) . . ? C33 C34 C35 120.3(2) . . ? C34 C35 C36 120.2(2) . . ? C35 C36 C37 120.8(2) . . ? C36 C37 C32 118.05(19) . . ? C36 C37 B2 132.62(19) . . ? C32 C37 B2 109.33(18) . . ? C8 B1 C19 99.57(15) . . ? C8 B1 N2 106.99(16) . . ? C19 B1 N2 112.09(16) . . ? C8 B1 C7 112.22(16) . . ? C19 B1 C7 109.59(16) . . ? N2 B1 C7 115.28(16) . . ? C37 B2 C26 99.89(16) . . ? C37 B2 N1 110.60(16) . . ? C26 B2 N1 113.92(16) . . ? C37 B2 C25 110.11(16) . . ? C26 B2 C25 106.67(16) . . ? N1 B2 C25 114.62(16) . . ? C6 N1 C2 119.07(17) . . ? C6 N1 B2 125.33(17) . . ? C2 N1 B2 115.39(16) . . ? C24 N2 C20 118.81(17) . . ? C24 N2 B1 123.40(16) . . ? C20 N2 B1 116.66(16) . . ? N3 C39 C38 179.5(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.31 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.850 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.056 #===END data_1a _database_code_depnum_ccdc_archive 'CCDC 871061' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common diethylboronpicoline-LiOMe-TMEDA _chemical_melting_point ? _chemical_formula_moiety 'C17 H35 B Li N3 O' _chemical_formula_sum 'C17 H35 B Li N3 O' _chemical_formula_weight 315.23 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' Li Li -0.0003 0.0001 '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 Orthorhombic _symmetry_space_group_name_H-M 'Pna2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 10.166(4) _cell_length_b 13.303(6) _cell_length_c 15.011(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2030.2(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6009 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 18.16 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.86 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.031 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9482 _exptl_absorpt_correction_T_max 0.9761 _exptl_absorpt_process_details 'SADABS (Bruker,2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8205 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 18.16 _reflns_number_total 1421 _reflns_number_gt 1321 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+1.4832P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(3) _refine_ls_number_reflns 1421 _refine_ls_number_parameters 215 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1044 _refine_ls_wR_factor_gt 0.1014 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.104 _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 C2 C 0.0641(5) 0.6789(4) 0.6907(5) 0.0372(14) Uani 1 1 d . . . H2 H -0.0256 0.6973 0.6834 0.045 Uiso 1 1 calc R . . C3 C 0.1233(8) 0.7021(4) 0.7689(4) 0.0395(15) Uani 1 1 d . . . H3 H 0.0766 0.7364 0.8145 0.047 Uiso 1 1 calc R . . C4 C 0.2532(8) 0.6746(4) 0.7807(4) 0.0424(16) Uani 1 1 d . . . H4 H 0.2975 0.6881 0.8351 0.051 Uiso 1 1 calc R . . C5 C 0.3164(5) 0.6273(4) 0.7118(4) 0.0275(13) Uani 1 1 d . . . H5 H 0.4057 0.6076 0.7186 0.033 Uiso 1 1 calc R . . C6 C 0.2521(5) 0.6080(3) 0.6328(4) 0.0218(13) Uani 1 1 d . . . C7 C 0.3167(4) 0.5578(3) 0.5565(3) 0.0266(13) Uani 1 1 d . . . H7A H 0.4130 0.5621 0.5652 0.032 Uiso 1 1 calc R . . H7B H 0.2952 0.5960 0.5018 0.032 Uiso 1 1 calc R . . C8 C 0.2762(5) 0.3732(4) 0.6303(4) 0.0364(15) Uani 1 1 d . . . H8A H 0.2166 0.4068 0.6731 0.044 Uiso 1 1 calc R . . H8B H 0.2383 0.3063 0.6171 0.044 Uiso 1 1 calc R . . C9 C 0.4087(6) 0.3576(4) 0.6759(4) 0.0522(17) Uani 1 1 d . . . H9A H 0.4656 0.3168 0.6375 0.078 Uiso 1 1 calc R . . H9B H 0.3955 0.3229 0.7328 0.078 Uiso 1 1 calc R . . H9C H 0.4502 0.4229 0.6867 0.078 Uiso 1 1 calc R . . C10 C 0.3780(5) 0.3941(4) 0.4652(3) 0.0324(14) Uani 1 1 d . . . H10A H 0.4677 0.3942 0.4909 0.039 Uiso 1 1 calc R . . H10B H 0.3542 0.3232 0.4531 0.039 Uiso 1 1 calc R . . C11 C 0.3819(6) 0.4498(4) 0.3776(4) 0.0528(17) Uani 1 1 d . . . H11A H 0.2953 0.4462 0.3490 0.079 Uiso 1 1 calc R . . H11B H 0.4479 0.4191 0.3386 0.079 Uiso 1 1 calc R . . H11C H 0.4049 0.5203 0.3882 0.079 Uiso 1 1 calc R . . C12 C 0.0880(6) 0.3529(4) 0.4637(5) 0.065(2) Uani 1 1 d . . . H12A H 0.1407 0.3354 0.4113 0.097 Uiso 1 1 calc R . . H12B H -0.0038 0.3628 0.4458 0.097 Uiso 1 1 calc R . . H12C H 0.0930 0.2984 0.5074 0.097 Uiso 1 1 calc R . . C13 C -0.0090(8) 0.7316(4) 0.4182(4) 0.077(2) Uani 1 1 d . . . H13A H -0.0449 0.7662 0.3660 0.115 Uiso 1 1 calc R . . H13B H 0.0870 0.7379 0.4185 0.115 Uiso 1 1 calc R . . H13C H -0.0450 0.7619 0.4725 0.115 Uiso 1 1 calc R . . C14 C 0.0082(6) 0.5827(5) 0.3349(4) 0.0617(19) Uani 1 1 d . . . H14A H -0.0280 0.6183 0.2833 0.093 Uiso 1 1 calc R . . H14B H -0.0148 0.5113 0.3311 0.093 Uiso 1 1 calc R . . H14C H 0.1041 0.5899 0.3355 0.093 Uiso 1 1 calc R . . C15 C -0.1862(6) 0.6144(7) 0.4183(5) 0.100(3) Uani 1 1 d . . . H15A H -0.2224 0.6813 0.4332 0.120 Uiso 1 1 calc R . . H15B H -0.2164 0.5982 0.3573 0.120 Uiso 1 1 calc R . . C16 C -0.2429(7) 0.5472(7) 0.4739(5) 0.086(3) Uani 1 1 d . . . H16A H -0.2540 0.4841 0.4399 0.103 Uiso 1 1 calc R . . H16B H -0.3324 0.5726 0.4870 0.103 Uiso 1 1 calc R . . C17 C -0.2425(5) 0.5769(6) 0.6306(5) 0.078(2) Uani 1 1 d . . . H17A H -0.2252 0.6487 0.6218 0.118 Uiso 1 1 calc R . . H17B H -0.2040 0.5550 0.6872 0.118 Uiso 1 1 calc R . . H17C H -0.3377 0.5652 0.6316 0.118 Uiso 1 1 calc R . . C18 C -0.2115(6) 0.4145(4) 0.5753(6) 0.078(2) Uani 1 1 d . . . H18A H -0.3068 0.4042 0.5795 0.117 Uiso 1 1 calc R . . H18B H -0.1699 0.3943 0.6314 0.117 Uiso 1 1 calc R . . H18C H -0.1762 0.3737 0.5265 0.117 Uiso 1 1 calc R . . Li1 Li 0.0229(7) 0.5504(6) 0.5294(5) 0.031(2) Uani 1 1 d . . . B1 B 0.2772(5) 0.4377(4) 0.5397(4) 0.0230(15) Uani 1 1 d . . . N1 N 0.1239(4) 0.6316(3) 0.6227(3) 0.0275(11) Uani 1 1 d . . . N2 N -0.0454(4) 0.6243(3) 0.4148(3) 0.0331(12) Uani 1 1 d . . . N3 N -0.1844(4) 0.5203(3) 0.5583(3) 0.0323(11) Uani 1 1 d . . . O1 O 0.1375(3) 0.4433(2) 0.5023(2) 0.0319(10) 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 C2 0.036(3) 0.028(4) 0.048(4) -0.012(3) 0.004(5) -0.005(3) C3 0.059(5) 0.017(3) 0.043(5) -0.005(3) 0.019(4) -0.008(3) C4 0.079(6) 0.017(4) 0.031(4) -0.005(3) -0.010(4) -0.012(3) C5 0.032(3) 0.017(3) 0.033(4) -0.004(3) -0.011(4) -0.004(3) C6 0.028(4) 0.002(3) 0.036(4) 0.002(3) -0.003(4) -0.004(3) C7 0.021(3) 0.030(3) 0.029(3) -0.001(3) 0.004(3) 0.000(3) C8 0.038(3) 0.021(3) 0.051(4) -0.006(3) 0.008(3) 0.005(3) C9 0.071(5) 0.050(4) 0.036(4) 0.011(3) -0.002(3) 0.018(3) C10 0.033(3) 0.018(3) 0.047(4) -0.005(3) 0.002(3) -0.001(3) C11 0.081(4) 0.035(4) 0.043(4) -0.003(4) 0.019(3) 0.017(3) C12 0.052(4) 0.034(4) 0.108(5) -0.040(4) -0.027(4) 0.005(3) C13 0.140(6) 0.021(4) 0.069(4) 0.007(3) -0.011(4) 0.004(4) C14 0.075(5) 0.063(5) 0.047(4) -0.012(4) -0.012(4) 0.012(4) C15 0.031(5) 0.166(8) 0.101(6) 0.082(6) -0.018(4) -0.014(5) C16 0.041(4) 0.135(7) 0.081(6) 0.052(5) -0.023(4) -0.027(5) C17 0.031(4) 0.097(5) 0.106(6) -0.050(5) 0.030(4) -0.007(4) C18 0.053(4) 0.036(4) 0.146(7) 0.005(4) -0.006(4) -0.009(3) Li1 0.024(4) 0.028(5) 0.041(6) -0.004(4) -0.004(4) -0.005(4) B1 0.023(4) 0.021(4) 0.025(4) 0.003(3) 0.007(3) 0.003(3) N1 0.033(3) 0.014(2) 0.036(3) -0.011(2) 0.003(3) 0.003(2) N2 0.027(3) 0.030(3) 0.042(3) 0.001(2) 0.006(2) -0.001(2) N3 0.026(2) 0.025(3) 0.045(3) 0.004(3) -0.001(3) -0.001(2) O1 0.026(2) 0.021(2) 0.049(2) -0.0127(19) -0.0056(18) 0.0023(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 N1 1.345(7) . ? C2 C3 1.354(7) . ? C2 H2 0.9500 . ? C3 C4 1.382(8) . ? C3 H3 0.9500 . ? C4 C5 1.371(7) . ? C4 H4 0.9500 . ? C5 C6 1.379(6) . ? C5 H5 0.9500 . ? C6 N1 1.348(6) . ? C6 C7 1.478(7) . ? C7 B1 1.667(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.525(7) . ? C8 B1 1.609(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.511(7) . ? C10 B1 1.624(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O1 1.427(6) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 N2 1.475(6) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N2 1.429(6) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.352(9) . ? C15 N2 1.438(7) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N3 1.444(7) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 N3 1.447(7) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 N3 1.458(6) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? Li1 O1 1.885(8) . ? Li1 N1 2.046(9) . ? Li1 N2 2.099(9) . ? Li1 N3 2.188(8) . ? B1 O1 1.529(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 N1 C2 C3 124.3(5) . . ? N1 C2 H2 117.9 . . ? C3 C2 H2 117.9 . . ? C2 C3 C4 118.4(5) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 118.2(5) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? C4 C5 C6 120.8(5) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? N1 C6 C5 120.7(4) . . ? N1 C6 C7 116.6(5) . . ? C5 C6 C7 122.6(5) . . ? C6 C7 B1 116.3(4) . . ? C6 C7 H7A 108.2 . . ? B1 C7 H7A 108.2 . . ? C6 C7 H7B 108.2 . . ? B1 C7 H7B 108.2 . . ? H7A C7 H7B 107.4 . . ? C9 C8 B1 116.5(4) . . ? C9 C8 H8A 108.2 . . ? B1 C8 H8A 108.2 . . ? C9 C8 H8B 108.2 . . ? B1 C8 H8B 108.2 . . ? H8A C8 H8B 107.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 B1 116.1(4) . . ? C11 C10 H10A 108.3 . . ? B1 C10 H10A 108.3 . . ? C11 C10 H10B 108.3 . . ? B1 C10 H10B 108.3 . . ? H10A C10 H10B 107.4 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 N2 120.5(6) . . ? C16 C15 H15A 107.2 . . ? N2 C15 H15A 107.2 . . ? C16 C15 H15B 107.2 . . ? N2 C15 H15B 107.2 . . ? H15A C15 H15B 106.8 . . ? C15 C16 N3 122.0(6) . . ? C15 C16 H16A 106.8 . . ? N3 C16 H16A 106.8 . . ? C15 C16 H16B 106.8 . . ? N3 C16 H16B 106.8 . . ? H16A C16 H16B 106.7 . . ? N3 C17 H17A 109.5 . . ? N3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N3 C18 H18A 109.5 . . ? N3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O1 Li1 N1 103.7(4) . . ? O1 Li1 N2 112.4(4) . . ? N1 Li1 N2 118.7(4) . . ? O1 Li1 N3 120.0(4) . . ? N1 Li1 N3 116.4(4) . . ? N2 Li1 N3 85.9(3) . . ? O1 B1 C8 109.3(4) . . ? O1 B1 C10 110.5(4) . . ? C8 B1 C10 113.3(4) . . ? O1 B1 C7 103.5(4) . . ? C8 B1 C7 112.6(4) . . ? C10 B1 C7 107.2(4) . . ? C2 N1 C6 117.5(4) . . ? C2 N1 Li1 122.7(4) . . ? C6 N1 Li1 116.0(4) . . ? C14 N2 C15 112.0(5) . . ? C14 N2 C13 107.9(5) . . ? C15 N2 C13 109.7(5) . . ? C14 N2 Li1 112.3(4) . . ? C15 N2 Li1 104.9(4) . . ? C13 N2 Li1 110.0(4) . . ? C16 N3 C17 111.1(5) . . ? C16 N3 C18 108.4(5) . . ? C17 N3 C18 107.1(5) . . ? C16 N3 Li1 100.3(4) . . ? C17 N3 Li1 116.5(4) . . ? C18 N3 Li1 113.2(4) . . ? C12 O1 B1 115.8(4) . . ? C12 O1 Li1 120.4(4) . . ? B1 O1 Li1 122.1(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 18.16 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.153 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.033 #===END data_2a _database_code_depnum_ccdc_archive 'CCDC 871062' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common BBN-picoline-LiOMe-TMEDA _chemical_melting_point ? _chemical_formula_moiety 'C21 H39 B Li N3 O' _chemical_formula_sum 'C21 H39 B Li N3 O' _chemical_formula_weight 367.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 '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 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.537(2) _cell_length_b 19.523(5) _cell_length_c 11.571(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.102(3) _cell_angle_gamma 90.00 _cell_volume 2153.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6077 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 18.51 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.133 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9733 _exptl_absorpt_correction_T_max 0.9786 _exptl_absorpt_process_details 'SADABS (Bruker,2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10308 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 18.53 _reflns_number_total 1602 _reflns_number_gt 1437 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+19.6287P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1602 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0974 _refine_ls_R_factor_gt 0.0915 _refine_ls_wR_factor_ref 0.2649 _refine_ls_wR_factor_gt 0.2621 _refine_ls_goodness_of_fit_ref 1.292 _refine_ls_restrained_S_all 1.292 _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 C2 C 0.3801(13) 0.6681(5) 0.0144(9) 0.028(3) Uani 1 1 d . . . H2 H 0.4079 0.6969 -0.0473 0.033 Uiso 1 1 calc R . . C3 C 0.2436(12) 0.6723(5) 0.0479(9) 0.027(3) Uani 1 1 d . . . H3 H 0.1791 0.7027 0.0113 0.033 Uiso 1 1 calc R . . C4 C 0.2036(11) 0.6300(6) 0.1380(9) 0.030(3) Uani 1 1 d . . . H4 H 0.1100 0.6309 0.1647 0.036 Uiso 1 1 calc R . . C5 C 0.2990(12) 0.5877(5) 0.1872(9) 0.026(3) Uani 1 1 d . . . H5 H 0.2723 0.5594 0.2499 0.031 Uiso 1 1 calc R . . C6 C 0.4369(11) 0.5845(5) 0.1477(9) 0.025(3) Uani 1 1 d . . . C7 C 0.5400(10) 0.5324(5) 0.1937(9) 0.027(3) Uani 1 1 d . . . H7A H 0.5505 0.4968 0.1335 0.032 Uiso 1 1 calc R . . H7B H 0.4970 0.5100 0.2611 0.032 Uiso 1 1 calc R . . C8 C 0.7802(10) 0.4979(5) 0.3063(8) 0.021(3) Uani 1 1 d . . . H8 H 0.7750 0.4546 0.2601 0.025 Uiso 1 1 calc R . . C9 C 0.9358(10) 0.5175(5) 0.3227(8) 0.027(3) Uani 1 1 d . . . H9A H 0.9799 0.5193 0.2460 0.032 Uiso 1 1 calc R . . H9B H 0.9838 0.4814 0.3686 0.032 Uiso 1 1 calc R . . C10 C 0.9579(10) 0.5871(5) 0.3839(8) 0.028(3) Uani 1 1 d . . . H10A H 0.9428 0.5811 0.4677 0.034 Uiso 1 1 calc R . . H10B H 1.0562 0.6019 0.3739 0.034 Uiso 1 1 calc R . . C11 C 0.8602(10) 0.6434(5) 0.3384(9) 0.033(3) Uani 1 1 d . . . H11A H 0.8633 0.6818 0.3943 0.040 Uiso 1 1 calc R . . H11B H 0.8983 0.6607 0.2649 0.040 Uiso 1 1 calc R . . C12 C 0.7072(10) 0.6244(5) 0.3167(8) 0.022(3) Uani 1 1 d . . . H12 H 0.6604 0.6632 0.2750 0.026 Uiso 1 1 calc R . . C13 C 0.6250(11) 0.6099(5) 0.4280(8) 0.033(3) Uani 1 1 d . . . H13A H 0.6291 0.6511 0.4779 0.040 Uiso 1 1 calc R . . H13B H 0.5254 0.6017 0.4068 0.040 Uiso 1 1 calc R . . C14 C 0.6801(11) 0.5491(5) 0.4963(9) 0.035(3) Uani 1 1 d . . . H14A H 0.6104 0.5367 0.5551 0.042 Uiso 1 1 calc R . . H14B H 0.7673 0.5629 0.5378 0.042 Uiso 1 1 calc R . . C15 C 0.7113(11) 0.4849(5) 0.4226(8) 0.030(3) Uani 1 1 d . . . H15A H 0.7730 0.4542 0.4687 0.036 Uiso 1 1 calc R . . H15B H 0.6219 0.4603 0.4081 0.036 Uiso 1 1 calc R . . C16 C 0.8027(12) 0.5216(5) 0.0461(9) 0.038(3) Uani 1 1 d . . . H16A H 0.7276 0.5206 -0.0130 0.058 Uiso 1 1 calc R . . H16B H 0.8043 0.4781 0.0883 0.058 Uiso 1 1 calc R . . H16C H 0.8930 0.5286 0.0088 0.058 Uiso 1 1 calc R . . Li1 Li 0.6915(17) 0.6486(9) 0.0378(14) 0.034(4) Uani 1 1 d . . . B1 B 0.7000(12) 0.5575(6) 0.2341(10) 0.024(3) Uani 1 1 d . . . N1 N 0.4780(9) 0.6268(5) 0.0617(7) 0.028(2) Uani 1 1 d . . . O1 O 0.7784(6) 0.5759(3) 0.1237(5) 0.0210(17) Uani 1 1 d . . . C17 C 0.6431(12) 0.6590(6) -0.2190(10) 0.050(3) Uani 1 1 d . . . H17A H 0.5987 0.6139 -0.2116 0.075 Uiso 1 1 calc R . . H17B H 0.6730 0.6655 -0.2988 0.075 Uiso 1 1 calc R . . H17C H 0.5757 0.6948 -0.1990 0.075 Uiso 1 1 calc R . . C18 C 0.8718(12) 0.6193(6) -0.1879(9) 0.043(3) Uani 1 1 d . . . H18A H 0.9543 0.6197 -0.1361 0.065 Uiso 1 1 calc R . . H18B H 0.8979 0.6362 -0.2643 0.065 Uiso 1 1 calc R . . H18C H 0.8360 0.5724 -0.1949 0.065 Uiso 1 1 calc R . . C19 C 0.8214(11) 0.7327(5) -0.1381(9) 0.038(3) Uani 1 1 d . . . H19A H 0.8244 0.7508 -0.2180 0.045 Uiso 1 1 calc R . . H19B H 0.9189 0.7312 -0.1071 0.045 Uiso 1 1 calc R . . C20 C 0.7371(11) 0.7805(5) -0.0656(8) 0.026(3) Uani 1 1 d . . . H20A H 0.7796 0.8267 -0.0683 0.031 Uiso 1 1 calc R . . H20B H 0.6410 0.7838 -0.0990 0.031 Uiso 1 1 calc R . . C21 C 0.6164(11) 0.7953(5) 0.1134(9) 0.033(3) Uani 1 1 d . . . H21A H 0.5278 0.7879 0.0710 0.050 Uiso 1 1 calc R . . H21B H 0.6381 0.8444 0.1150 0.050 Uiso 1 1 calc R . . H21C H 0.6079 0.7784 0.1927 0.050 Uiso 1 1 calc R . . C22 C 0.8603(11) 0.7736(5) 0.1170(9) 0.034(3) Uani 1 1 d . . . H22A H 0.8526 0.7607 0.1985 0.051 Uiso 1 1 calc R . . H22B H 0.8804 0.8227 0.1115 0.051 Uiso 1 1 calc R . . H22C H 0.9364 0.7476 0.0821 0.051 Uiso 1 1 calc R . . N2 N 0.7643(8) 0.6630(4) -0.1412(6) 0.024(2) Uani 1 1 d . . . N3 N 0.7286(8) 0.7585(4) 0.0561(6) 0.023(2) 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 C2 0.035(8) 0.022(7) 0.026(6) 0.001(6) -0.005(6) 0.000(6) C3 0.030(8) 0.024(7) 0.028(7) 0.008(6) -0.005(6) 0.006(5) C4 0.031(7) 0.028(7) 0.031(7) -0.008(6) 0.000(6) 0.003(7) C5 0.033(8) 0.023(7) 0.021(6) -0.007(6) 0.005(6) -0.002(6) C6 0.030(8) 0.024(7) 0.022(7) -0.003(6) 0.001(6) -0.006(6) C7 0.033(7) 0.018(6) 0.029(6) 0.004(5) -0.001(5) 0.002(6) C8 0.043(7) 0.007(6) 0.013(6) 0.000(5) 0.001(5) -0.001(5) C9 0.026(7) 0.026(7) 0.028(7) 0.005(5) 0.002(5) 0.008(5) C10 0.028(6) 0.029(7) 0.027(6) 0.012(6) -0.009(5) 0.002(6) C11 0.036(7) 0.021(7) 0.043(7) -0.002(5) 0.001(6) 0.001(6) C12 0.033(7) 0.017(6) 0.016(6) 0.001(5) -0.007(5) 0.002(5) C13 0.039(7) 0.035(7) 0.026(7) 0.000(6) 0.007(6) 0.008(6) C14 0.035(7) 0.041(8) 0.028(7) 0.008(6) 0.006(5) 0.005(6) C15 0.036(7) 0.021(7) 0.034(7) 0.010(6) 0.002(6) -0.002(5) C16 0.064(8) 0.025(7) 0.027(7) 0.004(6) 0.004(6) 0.010(6) Li1 0.037(11) 0.033(11) 0.033(11) 0.003(9) 0.003(8) -0.004(9) B1 0.029(8) 0.017(7) 0.026(8) -0.003(6) 0.008(6) -0.001(6) N1 0.030(6) 0.030(5) 0.024(5) 0.002(5) -0.005(5) -0.004(5) O1 0.041(4) 0.011(4) 0.011(4) 0.000(3) -0.001(3) 0.001(3) C17 0.045(8) 0.065(9) 0.040(7) -0.018(7) -0.001(7) 0.003(7) C18 0.054(8) 0.040(8) 0.037(7) 0.004(6) 0.021(6) 0.005(7) C19 0.050(7) 0.036(8) 0.026(7) 0.016(6) -0.004(6) 0.000(7) C20 0.042(7) 0.012(6) 0.024(7) -0.002(5) 0.005(5) 0.008(5) C21 0.036(7) 0.034(7) 0.030(7) -0.002(6) 0.006(6) 0.004(6) C22 0.038(7) 0.032(7) 0.033(7) 0.005(5) -0.005(6) 0.004(6) N2 0.039(6) 0.011(5) 0.023(5) -0.001(4) 0.000(5) 0.001(5) N3 0.030(6) 0.021(5) 0.019(6) 0.003(4) 0.003(4) 0.005(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 C2 N1 1.343(12) . ? C2 C3 1.368(13) . ? C3 C4 1.389(14) . ? C4 C5 1.346(13) . ? C5 C6 1.402(13) . ? C6 N1 1.357(12) . ? C6 C7 1.504(14) . ? C7 B1 1.662(15) . ? C8 C15 1.530(13) . ? C8 C9 1.541(13) . ? C8 B1 1.617(15) . ? C9 C10 1.545(13) . ? C10 C11 1.527(13) . ? C11 C12 1.521(13) . ? C12 C13 1.546(13) . ? C12 B1 1.619(15) . ? C13 C14 1.515(14) . ? C14 C15 1.547(14) . ? C16 O1 1.411(11) . ? Li1 O1 1.913(18) . ? Li1 N1 2.104(18) . ? Li1 N3 2.185(18) . ? Li1 N2 2.214(18) . ? B1 O1 1.534(13) . ? C17 N2 1.454(13) . ? C18 N2 1.446(12) . ? C19 N2 1.467(13) . ? C19 C20 1.499(14) . ? C20 N3 1.476(12) . ? C21 N3 1.459(12) . ? C22 N3 1.458(12) . ? 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 N1 C2 C3 125.3(9) . . ? C2 C3 C4 117.0(9) . . ? C5 C4 C3 119.2(10) . . ? C4 C5 C6 121.3(10) . . ? N1 C6 C5 119.9(9) . . ? N1 C6 C7 118.3(9) . . ? C5 C6 C7 121.7(10) . . ? C6 C7 B1 119.4(8) . . ? C15 C8 C9 111.2(8) . . ? C15 C8 B1 111.5(8) . . ? C9 C8 B1 109.2(7) . . ? C8 C9 C10 113.5(8) . . ? C11 C10 C9 113.4(8) . . ? C12 C11 C10 117.3(8) . . ? C11 C12 C13 114.0(8) . . ? C11 C12 B1 108.9(8) . . ? C13 C12 B1 109.2(8) . . ? C14 C13 C12 113.7(8) . . ? C13 C14 C15 114.6(8) . . ? C8 C15 C14 116.2(8) . . ? O1 Li1 N1 101.0(8) . . ? O1 Li1 N3 127.6(9) . . ? N1 Li1 N3 110.0(8) . . ? O1 Li1 N2 116.1(8) . . ? N1 Li1 N2 118.0(8) . . ? N3 Li1 N2 85.0(6) . . ? O1 B1 C8 111.4(8) . . ? O1 B1 C12 106.7(8) . . ? C8 B1 C12 105.1(8) . . ? O1 B1 C7 107.1(8) . . ? C8 B1 C7 110.8(8) . . ? C12 B1 C7 115.6(8) . . ? C2 N1 C6 117.1(8) . . ? C2 N1 Li1 119.5(9) . . ? C6 N1 Li1 120.9(9) . . ? C16 O1 B1 116.3(7) . . ? C16 O1 Li1 107.5(7) . . ? B1 O1 Li1 113.1(7) . . ? N2 C19 C20 112.8(8) . . ? N3 C20 C19 113.2(8) . . ? C18 N2 C17 107.4(8) . . ? C18 N2 C19 106.9(8) . . ? C17 N2 C19 110.8(8) . . ? C18 N2 Li1 120.8(8) . . ? C17 N2 Li1 108.2(8) . . ? C19 N2 Li1 102.6(7) . . ? C22 N3 C21 108.3(8) . . ? C22 N3 C20 109.9(7) . . ? C21 N3 C20 110.2(7) . . ? C22 N3 Li1 112.4(7) . . ? C21 N3 Li1 114.1(7) . . ? C20 N3 Li1 101.8(7) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 18.53 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.379 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.082 #===END data_2b _database_code_depnum_ccdc_archive 'CCDC 871063' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common BBNpicoline-LiOMe-2THF _chemical_melting_point ? _chemical_formula_moiety 'C23 H39 B Li N O3' _chemical_formula_sum 'C23 H39 B Li N O3' _chemical_formula_weight 395.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1997(5) _cell_length_b 10.0620(5) _cell_length_c 13.7746(7) _cell_angle_alpha 75.5130(10) _cell_angle_beta 85.6150(10) _cell_angle_gamma 66.2570(10) _cell_volume 1129.62(10) _cell_formula_units_Z 2 _cell_measurement_temperature 101(2) _cell_measurement_reflns_used 6906 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 25.49 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.44 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9532 _exptl_absorpt_correction_T_max 0.9683 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 101(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11471 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.52 _reflns_number_total 4176 _reflns_number_gt 3416 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+1.4511P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4176 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0708 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1486 _refine_ls_wR_factor_gt 0.1394 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 C2 C 0.3409(3) 0.5451(2) 0.26845(16) 0.0213(5) Uani 1 1 d . . . H2 H 0.4137 0.4443 0.2913 0.026 Uiso 1 1 calc R . . C3 C 0.1813(3) 0.5763(2) 0.27854(16) 0.0228(5) Uani 1 1 d . . . H3 H 0.1450 0.4991 0.3068 0.027 Uiso 1 1 calc R . . C4 C 0.0748(3) 0.7239(2) 0.24622(16) 0.0229(5) Uani 1 1 d . . . H4 H -0.0362 0.7505 0.2531 0.028 Uiso 1 1 calc R . . C5 C 0.1337(2) 0.8314(2) 0.20386(15) 0.0206(4) Uani 1 1 d . . . H5 H 0.0624 0.9329 0.1813 0.025 Uiso 1 1 calc R . . C6 C 0.2980(2) 0.7921(2) 0.19385(15) 0.0180(4) Uani 1 1 d . . . C7 C 0.3660(2) 0.9038(2) 0.14618(15) 0.0188(4) Uani 1 1 d . . . H7A H 0.2781 1.0042 0.1316 0.023 Uiso 1 1 calc R . . H7B H 0.4099 0.8832 0.0811 0.023 Uiso 1 1 calc R . . C8 C 0.5251(2) 1.0718(2) 0.17554(15) 0.0188(4) Uani 1 1 d . . . H8 H 0.5477 1.0893 0.1023 0.023 Uiso 1 1 calc R . . C9 C 0.3682(3) 1.1990(2) 0.19091(16) 0.0215(5) Uani 1 1 d . . . H9A H 0.3843 1.2937 0.1742 0.026 Uiso 1 1 calc R . . H9B H 0.2869 1.2096 0.1431 0.026 Uiso 1 1 calc R . . C10 C 0.3041(3) 1.1772(2) 0.29718(16) 0.0221(5) Uani 1 1 d . . . H10A H 0.1912 1.2471 0.2949 0.027 Uiso 1 1 calc R . . H10B H 0.3631 1.2047 0.3405 0.027 Uiso 1 1 calc R . . C11 C 0.3160(2) 1.0177(2) 0.34570(15) 0.0206(5) Uani 1 1 d . . . H11A H 0.2285 1.0037 0.3179 0.025 Uiso 1 1 calc R . . H11B H 0.2996 1.0083 0.4186 0.025 Uiso 1 1 calc R . . C12 C 0.4742(2) 0.8909(2) 0.33086(15) 0.0173(4) Uani 1 1 d . . . H12 H 0.4621 0.7938 0.3567 0.021 Uiso 1 1 calc R . . C13 C 0.6169(3) 0.8832(2) 0.38723(15) 0.0209(5) Uani 1 1 d . . . H13A H 0.5910 0.8767 0.4589 0.025 Uiso 1 1 calc R . . H13B H 0.7092 0.7902 0.3830 0.025 Uiso 1 1 calc R . . C14 C 0.6651(3) 1.0159(2) 0.34820(16) 0.0230(5) Uani 1 1 d . . . H14A H 0.7726 0.9884 0.3755 0.028 Uiso 1 1 calc R . . H14B H 0.5908 1.1015 0.3742 0.028 Uiso 1 1 calc R . . C15 C 0.6664(3) 1.0666(2) 0.23273(16) 0.0217(5) Uani 1 1 d . . . H15A H 0.7661 0.9981 0.2091 0.026 Uiso 1 1 calc R . . H15B H 0.6679 1.1677 0.2148 0.026 Uiso 1 1 calc R . . C16 C 0.7365(3) 0.7923(2) 0.10575(16) 0.0225(5) Uani 1 1 d . . . H16A H 0.6586 0.8142 0.0531 0.034 Uiso 1 1 calc R . . H16B H 0.8270 0.6983 0.1045 0.034 Uiso 1 1 calc R . . H16C H 0.7734 0.8737 0.0941 0.034 Uiso 1 1 calc R . . C17 C 0.6578(3) 0.4732(3) 0.07063(17) 0.0273(5) Uani 1 1 d . . . H17A H 0.5995 0.5812 0.0403 0.033 Uiso 1 1 calc R . . H17B H 0.5820 0.4240 0.0813 0.033 Uiso 1 1 calc R . . C18 C 0.7893(4) 0.4036(5) 0.0044(2) 0.0709(12) Uani 1 1 d . . . H18A H 0.7540 0.3563 -0.0387 0.085 Uiso 1 1 calc R . . H18B H 0.8233 0.4799 -0.0390 0.085 Uiso 1 1 calc R . . C19 C 0.9163(4) 0.2939(4) 0.0707(2) 0.0609(10) Uani 1 1 d . . . H19A H 1.0202 0.2846 0.0406 0.073 Uiso 1 1 calc R . . H19B H 0.9095 0.1952 0.0850 0.073 Uiso 1 1 calc R . . C20 C 0.8984(3) 0.3475(3) 0.16485(18) 0.0299(5) Uani 1 1 d . . . H20A H 0.9227 0.2625 0.2246 0.036 Uiso 1 1 calc R . . H20B H 0.9710 0.3978 0.1657 0.036 Uiso 1 1 calc R . . C21 C 0.7020(4) 0.3313(3) 0.4231(2) 0.0409(7) Uani 1 1 d . . . H21A H 0.7067 0.2793 0.3699 0.049 Uiso 1 1 calc R . . H21B H 0.5978 0.3521 0.4553 0.049 Uiso 1 1 calc R . . C22 C 0.8344(4) 0.2363(3) 0.4993(3) 0.0551(9) Uani 1 1 d . . . H22A H 0.8835 0.1322 0.4915 0.066 Uiso 1 1 calc R . . H22B H 0.7947 0.2352 0.5683 0.066 Uiso 1 1 calc R . . C23 C 0.9524(3) 0.3090(3) 0.47809(19) 0.0317(5) Uani 1 1 d . . . H23A H 1.0107 0.2946 0.5399 0.038 Uiso 1 1 calc R . . H23B H 1.0293 0.2699 0.4274 0.038 Uiso 1 1 calc R . . C24 C 0.8441(3) 0.4711(3) 0.43819(18) 0.0273(5) Uani 1 1 d . . . H24A H 0.7979 0.5195 0.4940 0.033 Uiso 1 1 calc R . . H24B H 0.9031 0.5263 0.3955 0.033 Uiso 1 1 calc R . . B1 B 0.5083(3) 0.9104(3) 0.21152(17) 0.0167(5) Uani 1 1 d . . . N1 N 0.4004(2) 0.64818(19) 0.22842(13) 0.0192(4) Uani 1 1 d . . . O1 O 0.66508(16) 0.77911(15) 0.20028(10) 0.0183(3) Uani 1 1 d . . . O2 O 0.73523(17) 0.45102(17) 0.16434(11) 0.0238(4) Uani 1 1 d . . . O3 O 0.7224(2) 0.46891(18) 0.38084(12) 0.0305(4) Uani 1 1 d . . . Li1 Li 0.6372(4) 0.5974(4) 0.2479(3) 0.0212(7) 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 C2 0.0248(11) 0.0183(10) 0.0226(11) -0.0058(8) -0.0019(9) -0.0093(9) C3 0.0275(12) 0.0239(11) 0.0222(11) -0.0062(9) 0.0012(9) -0.0151(10) C4 0.0196(11) 0.0285(12) 0.0235(11) -0.0092(9) 0.0011(8) -0.0107(9) C5 0.0200(11) 0.0202(11) 0.0210(11) -0.0047(8) -0.0028(8) -0.0067(9) C6 0.0214(10) 0.0207(10) 0.0142(10) -0.0068(8) -0.0026(8) -0.0085(9) C7 0.0208(10) 0.0199(10) 0.0158(10) -0.0034(8) -0.0005(8) -0.0086(9) C8 0.0228(11) 0.0203(10) 0.0143(10) -0.0032(8) 0.0022(8) -0.0105(9) C9 0.0247(11) 0.0173(10) 0.0222(11) -0.0036(8) -0.0020(9) -0.0081(9) C10 0.0221(11) 0.0196(11) 0.0240(11) -0.0070(9) 0.0012(9) -0.0066(9) C11 0.0223(11) 0.0242(11) 0.0176(10) -0.0074(8) 0.0041(8) -0.0107(9) C12 0.0219(11) 0.0158(10) 0.0160(10) -0.0028(8) 0.0010(8) -0.0101(8) C13 0.0262(11) 0.0217(11) 0.0153(10) -0.0035(8) -0.0018(8) -0.0101(9) C14 0.0242(11) 0.0233(11) 0.0249(11) -0.0066(9) -0.0046(9) -0.0114(9) C15 0.0225(11) 0.0192(11) 0.0263(11) -0.0044(9) 0.0021(9) -0.0122(9) C16 0.0241(11) 0.0258(11) 0.0195(11) -0.0082(9) 0.0063(9) -0.0112(9) C17 0.0259(12) 0.0294(12) 0.0232(11) -0.0090(9) -0.0071(9) -0.0047(10) C18 0.0482(19) 0.092(3) 0.0407(17) -0.0370(18) -0.0103(14) 0.0188(18) C19 0.0338(16) 0.085(2) 0.0447(18) -0.0337(17) 0.0019(13) 0.0067(16) C20 0.0190(11) 0.0339(13) 0.0307(13) -0.0075(10) -0.0019(9) -0.0040(10) C21 0.0532(17) 0.0369(15) 0.0390(15) 0.0090(11) -0.0154(13) -0.0322(14) C22 0.071(2) 0.0376(16) 0.0591(19) 0.0144(14) -0.0327(17) -0.0336(16) C23 0.0296(13) 0.0307(13) 0.0300(13) -0.0039(10) 0.0037(10) -0.0097(11) C24 0.0292(12) 0.0288(12) 0.0277(12) -0.0041(10) -0.0052(9) -0.0160(10) B1 0.0168(11) 0.0179(11) 0.0156(11) -0.0042(9) 0.0010(9) -0.0071(9) N1 0.0212(9) 0.0197(9) 0.0183(9) -0.0066(7) -0.0007(7) -0.0084(7) O1 0.0190(7) 0.0197(7) 0.0161(7) -0.0051(6) 0.0024(6) -0.0074(6) O2 0.0197(8) 0.0252(8) 0.0232(8) -0.0091(6) -0.0049(6) -0.0028(6) O3 0.0437(10) 0.0273(9) 0.0250(8) 0.0039(7) -0.0144(7) -0.0220(8) Li1 0.0212(18) 0.0207(18) 0.0212(18) -0.0032(14) -0.0026(14) -0.0084(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 N1 1.343(3) . ? C2 C3 1.377(3) . ? C2 H2 0.9500 . ? C3 C4 1.388(3) . ? C3 H3 0.9500 . ? C4 C5 1.383(3) . ? C4 H4 0.9500 . ? C5 C6 1.404(3) . ? C5 H5 0.9500 . ? C6 N1 1.355(3) . ? C6 C7 1.490(3) . ? C7 B1 1.676(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.539(3) . ? C8 C15 1.547(3) . ? C8 B1 1.641(3) . ? C8 H8 1.0000 . ? C9 C10 1.533(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.538(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.542(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.542(3) . ? C12 B1 1.627(3) . ? C12 H12 1.0000 . ? C13 C14 1.533(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.545(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O1 1.413(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 O2 1.446(3) . ? C17 C18 1.502(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.427(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.498(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O2 1.441(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 O3 1.442(3) . ? C21 C22 1.502(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.511(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.510(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 O3 1.429(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? B1 O1 1.544(3) . ? B1 Li1 2.806(4) . ? N1 Li1 2.050(4) . ? O1 Li1 1.895(4) . ? O2 Li1 1.982(4) . ? O3 Li1 1.964(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 N1 C2 C3 124.2(2) . . ? N1 C2 H2 117.9 . . ? C3 C2 H2 117.9 . . ? C2 C3 C4 118.0(2) . . ? C2 C3 H3 121.0 . . ? C4 C3 H3 121.0 . . ? C5 C4 C3 118.7(2) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C6 120.6(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? N1 C6 C5 119.88(19) . . ? N1 C6 C7 117.79(18) . . ? C5 C6 C7 122.33(19) . . ? C6 C7 B1 116.95(16) . . ? C6 C7 H7A 108.1 . . ? B1 C7 H7A 108.1 . . ? C6 C7 H7B 108.1 . . ? B1 C7 H7B 108.1 . . ? H7A C7 H7B 107.3 . . ? C9 C8 C15 111.97(17) . . ? C9 C8 B1 110.19(16) . . ? C15 C8 B1 109.79(16) . . ? C9 C8 H8 108.3 . . ? C15 C8 H8 108.3 . . ? B1 C8 H8 108.3 . . ? C10 C9 C8 114.81(17) . . ? C10 C9 H9A 108.6 . . ? C8 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? C8 C9 H9B 108.6 . . ? H9A C9 H9B 107.5 . . ? C9 C10 C11 114.96(17) . . ? C9 C10 H10A 108.5 . . ? C11 C10 H10A 108.5 . . ? C9 C10 H10B 108.5 . . ? C11 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C10 C11 C12 115.35(17) . . ? C10 C11 H11A 108.4 . . ? C12 C11 H11A 108.4 . . ? C10 C11 H11B 108.4 . . ? C12 C11 H11B 108.4 . . ? H11A C11 H11B 107.5 . . ? C13 C12 C11 113.60(16) . . ? C13 C12 B1 110.10(16) . . ? C11 C12 B1 109.13(16) . . ? C13 C12 H12 107.9 . . ? C11 C12 H12 107.9 . . ? B1 C12 H12 107.9 . . ? C14 C13 C12 114.94(17) . . ? C14 C13 H13A 108.5 . . ? C12 C13 H13A 108.5 . . ? C14 C13 H13B 108.5 . . ? C12 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? C13 C14 C15 114.59(17) . . ? C13 C14 H14A 108.6 . . ? C15 C14 H14A 108.6 . . ? C13 C14 H14B 108.6 . . ? C15 C14 H14B 108.6 . . ? H14A C14 H14B 107.6 . . ? C14 C15 C8 115.62(17) . . ? C14 C15 H15A 108.4 . . ? C8 C15 H15A 108.4 . . ? C14 C15 H15B 108.4 . . ? C8 C15 H15B 108.4 . . ? H15A C15 H15B 107.4 . . ? O1 C16 H16A 109.5 . . ? O1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C17 C18 105.36(19) . . ? O2 C17 H17A 110.7 . . ? C18 C17 H17A 110.7 . . ? O2 C17 H17B 110.7 . . ? C18 C17 H17B 110.7 . . ? H17A C17 H17B 108.8 . . ? C19 C18 C17 105.7(2) . . ? C19 C18 H18A 110.6 . . ? C17 C18 H18A 110.6 . . ? C19 C18 H18B 110.6 . . ? C17 C18 H18B 110.6 . . ? H18A C18 H18B 108.7 . . ? C18 C19 C20 106.1(2) . . ? C18 C19 H19A 110.5 . . ? C20 C19 H19A 110.5 . . ? C18 C19 H19B 110.5 . . ? C20 C19 H19B 110.5 . . ? H19A C19 H19B 108.7 . . ? O2 C20 C19 105.97(19) . . ? O2 C20 H20A 110.5 . . ? C19 C20 H20A 110.5 . . ? O2 C20 H20B 110.5 . . ? C19 C20 H20B 110.5 . . ? H20A C20 H20B 108.7 . . ? O3 C21 C22 107.1(2) . . ? O3 C21 H21A 110.3 . . ? C22 C21 H21A 110.3 . . ? O3 C21 H21B 110.3 . . ? C22 C21 H21B 110.3 . . ? H21A C21 H21B 108.6 . . ? C21 C22 C23 104.7(2) . . ? C21 C22 H22A 110.8 . . ? C23 C22 H22A 110.8 . . ? C21 C22 H22B 110.8 . . ? C23 C22 H22B 110.8 . . ? H22A C22 H22B 108.9 . . ? C24 C23 C22 101.4(2) . . ? C24 C23 H23A 111.5 . . ? C22 C23 H23A 111.5 . . ? C24 C23 H23B 111.5 . . ? C22 C23 H23B 111.5 . . ? H23A C23 H23B 109.3 . . ? O3 C24 C23 105.45(18) . . ? O3 C24 H24A 110.7 . . ? C23 C24 H24A 110.7 . . ? O3 C24 H24B 110.7 . . ? C23 C24 H24B 110.7 . . ? H24A C24 H24B 108.8 . . ? O1 B1 C12 107.25(16) . . ? O1 B1 C8 111.78(16) . . ? C12 B1 C8 104.68(16) . . ? O1 B1 C7 107.70(16) . . ? C12 B1 C7 113.10(16) . . ? C8 B1 C7 112.28(16) . . ? O1 B1 Li1 39.73(11) . . ? C12 B1 Li1 87.58(13) . . ? C8 B1 Li1 151.46(16) . . ? C7 B1 Li1 85.07(13) . . ? C2 N1 C6 118.58(18) . . ? C2 N1 Li1 119.85(17) . . ? C6 N1 Li1 120.20(17) . . ? C16 O1 B1 116.54(15) . . ? C16 O1 Li1 113.95(16) . . ? B1 O1 Li1 108.90(16) . . ? C20 O2 C17 109.29(16) . . ? C20 O2 Li1 128.51(17) . . ? C17 O2 Li1 119.30(16) . . ? C24 O3 C21 108.06(17) . . ? C24 O3 Li1 126.76(17) . . ? C21 O3 Li1 123.26(17) . . ? O1 Li1 O3 120.21(19) . . ? O1 Li1 O2 114.32(19) . . ? O3 Li1 O2 100.01(17) . . ? O1 Li1 N1 106.48(17) . . ? O3 Li1 N1 112.89(18) . . ? O2 Li1 N1 101.46(17) . . ? O1 Li1 B1 31.37(8) . . ? O3 Li1 B1 121.73(17) . . ? O2 Li1 B1 135.07(17) . . ? N1 Li1 B1 78.44(13) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.52 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.038 _refine_diff_density_min -0.645 _refine_diff_density_rms 0.055 #===END data_6 _database_code_depnum_ccdc_archive 'CCDC 871064' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common diethylboronpicoline-benzaldehyde _chemical_melting_point ? _chemical_formula_moiety 'C17 H21 B N2' _chemical_formula_sum 'C17 H21 B N2' _chemical_formula_weight 264.17 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 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.4473(4) _cell_length_b 9.7852(6) _cell_length_c 20.4386(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1489.43(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7550 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 23.25 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9719 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12556 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 23.26 _reflns_number_total 2145 _reflns_number_gt 2001 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+0.1741P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 2145 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0696 _refine_ls_wR_factor_gt 0.0676 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 C2 C 0.2726(2) 0.84545(16) 0.32883(8) 0.0238(4) Uani 1 1 d . . . H2 H 0.3529 0.8354 0.2930 0.029 Uiso 1 1 calc R . . C3 C 0.1993(2) 0.97098(17) 0.34013(8) 0.0258(4) Uani 1 1 d . . . H3 H 0.2267 1.0464 0.3126 0.031 Uiso 1 1 calc R . . C4 C 0.0827(2) 0.98565(18) 0.39321(8) 0.0277(4) Uani 1 1 d . . . H4 H 0.0298 1.0718 0.4026 0.033 Uiso 1 1 calc R . . C5 C 0.0459(2) 0.87506(16) 0.43124(8) 0.0261(4) Uani 1 1 d . . . H5 H -0.0338 0.8849 0.4672 0.031 Uiso 1 1 calc R . . C6 C 0.1230(2) 0.74641(16) 0.41857(8) 0.0202(4) Uani 1 1 d . . . C7 C 0.0912(2) 0.63168(16) 0.45952(8) 0.0229(4) Uani 1 1 d . . . H7 H -0.0074 0.6338 0.4890 0.027 Uiso 1 1 calc R . . C8 C 0.1990(2) 0.51751(15) 0.45778(7) 0.0188(4) Uani 1 1 d . . . C9 C 0.1955(2) 0.41239(16) 0.51037(7) 0.0194(4) Uani 1 1 d . . . C10 C 0.1310(2) 0.44328(17) 0.57280(8) 0.0253(4) Uani 1 1 d . . . H10 H 0.0805 0.5308 0.5810 0.030 Uiso 1 1 calc R . . C11 C 0.1396(2) 0.34864(18) 0.62290(8) 0.0299(4) Uani 1 1 d . . . H11 H 0.0951 0.3715 0.6651 0.036 Uiso 1 1 calc R . . C12 C 0.2127(2) 0.22059(18) 0.61184(8) 0.0304(4) Uani 1 1 d . . . H12 H 0.2221 0.1566 0.6466 0.036 Uiso 1 1 calc R . . C13 C 0.2718(2) 0.18646(17) 0.54993(8) 0.0299(4) Uani 1 1 d . . . H13 H 0.3180 0.0976 0.5417 0.036 Uiso 1 1 calc R . . C14 C 0.2640(2) 0.28125(16) 0.49984(8) 0.0243(4) Uani 1 1 d . . . H14 H 0.3060 0.2568 0.4575 0.029 Uiso 1 1 calc R . . C15 C 0.1558(2) 0.52142(16) 0.29584(8) 0.0252(4) Uani 1 1 d . . . H15A H 0.0380 0.5259 0.3182 0.030 Uiso 1 1 calc R . . H15B H 0.1480 0.5787 0.2560 0.030 Uiso 1 1 calc R . . C16 C 0.1911(3) 0.37414(18) 0.27547(10) 0.0440(5) Uani 1 1 d . . . H16A H 0.2990 0.3704 0.2481 0.066 Uiso 1 1 calc R . . H16B H 0.0881 0.3395 0.2506 0.066 Uiso 1 1 calc R . . H16C H 0.2089 0.3177 0.3146 0.066 Uiso 1 1 calc R . . C17 C 0.5076(2) 0.59474(16) 0.31321(8) 0.0212(4) Uani 1 1 d . . . H17A H 0.5457 0.5018 0.3000 0.025 Uiso 1 1 calc R . . H17B H 0.5017 0.6511 0.2730 0.025 Uiso 1 1 calc R . . C18 C 0.6518(2) 0.65472(17) 0.35811(8) 0.0268(4) Uani 1 1 d . . . H18A H 0.6232 0.7504 0.3676 0.040 Uiso 1 1 calc R . . H18B H 0.7689 0.6495 0.3364 0.040 Uiso 1 1 calc R . . H18C H 0.6556 0.6027 0.3991 0.040 Uiso 1 1 calc R . . B1 B 0.3081(3) 0.58502(19) 0.34399(8) 0.0212(4) Uani 1 1 d . . . N1 N 0.23659(17) 0.73438(13) 0.36611(6) 0.0190(3) Uani 1 1 d . . . N2 N 0.31751(18) 0.50378(14) 0.40896(6) 0.0203(3) Uani 1 1 d . . . H1 H 0.398(2) 0.4396(17) 0.4130(8) 0.023(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0209(8) 0.0253(9) 0.0252(8) 0.0030(8) 0.0008(7) 0.0004(8) C3 0.0228(9) 0.0217(9) 0.0330(9) 0.0047(7) -0.0011(8) 0.0010(8) C4 0.0253(9) 0.0187(9) 0.0392(10) -0.0031(8) -0.0008(8) 0.0049(8) C5 0.0237(9) 0.0241(10) 0.0306(10) -0.0034(8) 0.0057(8) 0.0063(8) C6 0.0171(9) 0.0226(9) 0.0208(8) -0.0022(7) -0.0014(7) 0.0008(7) C7 0.0194(9) 0.0250(9) 0.0242(9) -0.0009(7) 0.0039(7) 0.0006(7) C8 0.0183(8) 0.0198(8) 0.0182(8) -0.0045(7) -0.0017(7) -0.0029(7) C9 0.0157(8) 0.0205(8) 0.0218(8) -0.0006(7) -0.0003(7) -0.0045(7) C10 0.0265(9) 0.0236(9) 0.0258(9) -0.0023(7) 0.0027(8) -0.0050(8) C11 0.0330(10) 0.0342(11) 0.0225(9) 0.0022(8) 0.0038(8) -0.0094(9) C12 0.0272(9) 0.0327(10) 0.0311(10) 0.0133(8) -0.0004(8) -0.0057(8) C13 0.0246(10) 0.0243(9) 0.0407(11) 0.0092(8) 0.0050(8) 0.0001(8) C14 0.0206(9) 0.0248(10) 0.0276(9) 0.0014(7) 0.0055(7) -0.0008(7) C15 0.0245(9) 0.0254(9) 0.0257(9) -0.0024(7) -0.0014(7) 0.0051(8) C16 0.0390(11) 0.0377(11) 0.0553(12) -0.0192(10) -0.0124(10) 0.0049(10) C17 0.0255(9) 0.0199(9) 0.0182(8) 0.0023(7) 0.0012(7) 0.0044(7) C18 0.0234(9) 0.0273(10) 0.0297(9) 0.0024(8) 0.0018(8) 0.0019(8) B1 0.0253(10) 0.0188(10) 0.0195(9) -0.0002(8) 0.0013(8) 0.0047(9) N1 0.0178(7) 0.0195(7) 0.0196(7) 0.0001(6) -0.0021(6) 0.0013(6) N2 0.0195(8) 0.0189(7) 0.0225(7) -0.0005(6) 0.0028(6) 0.0049(7) _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 C2 N1 1.354(2) . ? C2 C3 1.364(2) . ? C2 H2 0.9500 . ? C3 C4 1.397(2) . ? C3 H3 0.9500 . ? C4 C5 1.360(2) . ? C4 H4 0.9500 . ? C5 C6 1.408(2) . ? C5 H5 0.9500 . ? C6 N1 1.371(2) . ? C6 C7 1.420(2) . ? C7 C8 1.376(2) . ? C7 H7 0.9500 . ? C8 N2 1.3387(19) . ? C8 C9 1.488(2) . ? C9 C10 1.396(2) . ? C9 C14 1.398(2) . ? C10 C11 1.382(2) . ? C10 H10 0.9500 . ? C11 C12 1.385(3) . ? C11 H11 0.9500 . ? C12 C13 1.381(2) . ? C12 H12 0.9500 . ? C13 C14 1.383(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.523(2) . ? C15 B1 1.626(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.529(2) . ? C17 B1 1.616(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? B1 N2 1.549(2) . ? B1 N1 1.620(2) . ? N2 H1 0.872(18) . ? 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 N1 C2 C3 123.26(15) . . ? N1 C2 H2 118.4 . . ? C3 C2 H2 118.4 . . ? C2 C3 C4 118.21(15) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C5 C4 C3 119.17(16) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 121.61(15) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? N1 C6 C5 118.19(14) . . ? N1 C6 C7 119.74(14) . . ? C5 C6 C7 122.03(14) . . ? C8 C7 C6 121.94(14) . . ? C8 C7 H7 119.0 . . ? C6 C7 H7 119.0 . . ? N2 C8 C7 119.03(14) . . ? N2 C8 C9 118.73(13) . . ? C7 C8 C9 122.15(13) . . ? C10 C9 C14 117.71(14) . . ? C10 C9 C8 121.09(14) . . ? C14 C9 C8 121.14(13) . . ? C11 C10 C9 121.07(16) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 120.23(15) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 119.59(15) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.19(16) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C9 121.15(15) . . ? C13 C14 H14 119.4 . . ? C9 C14 H14 119.4 . . ? C16 C15 B1 114.02(14) . . ? C16 C15 H15A 108.7 . . ? B1 C15 H15A 108.7 . . ? C16 C15 H15B 108.7 . . ? B1 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 B1 115.74(13) . . ? C18 C17 H17A 108.3 . . ? B1 C17 H17A 108.3 . . ? C18 C17 H17B 108.3 . . ? B1 C17 H17B 108.3 . . ? H17A C17 H17B 107.4 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 B1 C17 108.82(13) . . ? N2 B1 N1 103.80(12) . . ? C17 B1 N1 110.97(13) . . ? N2 B1 C15 110.72(14) . . ? C17 B1 C15 115.37(13) . . ? N1 B1 C15 106.53(12) . . ? C2 N1 C6 119.56(13) . . ? C2 N1 B1 120.14(12) . . ? C6 N1 B1 119.91(12) . . ? C8 N2 B1 123.90(13) . . ? C8 N2 H1 117.0(11) . . ? B1 N2 H1 118.8(11) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.129 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.029 #===END data_8 _database_code_depnum_ccdc_archive 'CCDC 871065' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common diethylboronpicoline-13dicyanobenzene _chemical_melting_point ? _chemical_formula_moiety 'C28 H36 B2 N4' _chemical_formula_sum 'C28 H36 B2 N4' _chemical_formula_weight 450.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.285(2) _cell_length_b 24.538(5) _cell_length_c 10.285(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.67 _cell_angle_gamma 90.00 _cell_volume 2590.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6926 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 23.38 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.67 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.154 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9563 _exptl_absorpt_correction_T_max 0.9886 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22851 _diffrn_reflns_av_R_equivalents 0.0682 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 23.96 _reflns_number_total 4026 _reflns_number_gt 2599 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0579P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4026 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.0993 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.940 _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 C2 C 0.2785(2) 0.31950(8) 1.03072(19) 0.0627(6) Uani 1 1 d . . . H2 H 0.3189 0.2857 1.0259 0.075 Uiso 1 1 calc R . . C3 C 0.1652(2) 0.32247(10) 1.0910(2) 0.0736(6) Uani 1 1 d . . . H3 H 0.1290 0.2916 1.1266 0.088 Uiso 1 1 calc R . . C4 C 0.1047(2) 0.37275(10) 1.09812(19) 0.0708(6) Uani 1 1 d . . . H4 H 0.0276 0.3762 1.1398 0.085 Uiso 1 1 calc R . . C5 C 0.15924(18) 0.41680(9) 1.04370(18) 0.0589(5) Uani 1 1 d . . . H5 H 0.1190 0.4506 1.0488 0.071 Uiso 1 1 calc R . . C6 C 0.27582(17) 0.41241(8) 0.97946(16) 0.0465(5) Uani 1 1 d . . . C7 C 0.32873(17) 0.45691(7) 0.91395(17) 0.0488(5) Uani 1 1 d . . . H7 H 0.2967 0.4917 0.9281 0.059 Uiso 1 1 calc R . . C8 C 0.42569(17) 0.45047(7) 0.83023(16) 0.0443(4) Uani 1 1 d . . . C9 C 0.57913(18) 0.37353(8) 1.05682(19) 0.0582(5) Uani 1 1 d . . . H9A H 0.5483 0.4072 1.0936 0.070 Uiso 1 1 calc R . . H9B H 0.5718 0.3452 1.1217 0.070 Uiso 1 1 calc R . . C10 C 0.72287(19) 0.38046(9) 1.0315(2) 0.0836(7) Uani 1 1 d . . . H10A H 0.7562 0.3468 0.9994 0.125 Uiso 1 1 calc R . . H10B H 0.7709 0.3902 1.1112 0.125 Uiso 1 1 calc R . . H10C H 0.7319 0.4087 0.9681 0.125 Uiso 1 1 calc R . . C11 C 0.5115(2) 0.29983(8) 0.87016(19) 0.0664(6) Uani 1 1 d . . . H11A H 0.6003 0.2995 0.8435 0.080 Uiso 1 1 calc R . . H11B H 0.5062 0.2728 0.9384 0.080 Uiso 1 1 calc R . . C12 C 0.4220(2) 0.28211(10) 0.7546(2) 0.0956(8) Uani 1 1 d . . . H12A H 0.3338 0.2809 0.7799 0.143 Uiso 1 1 calc R . . H12B H 0.4474 0.2466 0.7264 0.143 Uiso 1 1 calc R . . H12C H 0.4283 0.3077 0.6846 0.143 Uiso 1 1 calc R . . C13 C 0.02517(19) 0.67436(8) 0.25432(18) 0.0597(5) Uani 1 1 d . . . H13 H -0.0461 0.6547 0.2194 0.072 Uiso 1 1 calc R . . C14 C 0.0507(2) 0.72397(8) 0.2021(2) 0.0673(6) Uani 1 1 d . . . H14 H -0.0010 0.7377 0.1321 0.081 Uiso 1 1 calc R . . C15 C 0.1557(2) 0.75351(9) 0.2561(2) 0.0677(6) Uani 1 1 d . . . H15 H 0.1732 0.7881 0.2248 0.081 Uiso 1 1 calc R . . C16 C 0.23263(19) 0.73179(7) 0.3542(2) 0.0591(5) Uani 1 1 d . . . H16 H 0.3031 0.7517 0.3899 0.071 Uiso 1 1 calc R . . C17 C 0.20771(17) 0.67963(7) 0.40303(17) 0.0462(5) Uani 1 1 d . . . C18 C 0.29470(17) 0.65348(7) 0.49557(17) 0.0495(5) Uani 1 1 d . . . H18 H 0.3600 0.6740 0.5390 0.059 Uiso 1 1 calc R . . C19 C 0.28583(16) 0.59924(7) 0.52309(16) 0.0435(5) Uani 1 1 d . . . C20 C -0.02769(18) 0.62278(8) 0.55247(19) 0.0615(6) Uani 1 1 d . . . H20A H -0.0524 0.5919 0.6045 0.074 Uiso 1 1 calc R . . H20B H 0.0323 0.6449 0.6067 0.074 Uiso 1 1 calc R . . C21 C -0.1508(2) 0.65691(9) 0.5177(2) 0.0814(7) Uani 1 1 d . . . H21A H -0.1268 0.6900 0.4755 0.122 Uiso 1 1 calc R . . H21B H -0.1928 0.6656 0.5957 0.122 Uiso 1 1 calc R . . H21C H -0.2094 0.6364 0.4601 0.122 Uiso 1 1 calc R . . C22 C -0.03675(18) 0.55849(8) 0.3424(2) 0.0605(6) Uani 1 1 d . . . H22A H -0.0695 0.5305 0.3984 0.073 Uiso 1 1 calc R . . H22B H -0.1116 0.5781 0.3042 0.073 Uiso 1 1 calc R . . C23 C 0.0289(2) 0.53075(9) 0.2343(2) 0.0795(7) Uani 1 1 d . . . H23A H 0.0594 0.5577 0.1758 0.119 Uiso 1 1 calc R . . H23B H -0.0321 0.5071 0.1877 0.119 Uiso 1 1 calc R . . H23C H 0.1013 0.5097 0.2702 0.119 Uiso 1 1 calc R . . C24 C 0.45985(17) 0.49534(7) 0.74217(16) 0.0427(4) Uani 1 1 d . . . C25 C 0.36303(16) 0.52582(7) 0.67636(16) 0.0434(4) Uani 1 1 d . . . H25 H 0.2762 0.5173 0.6868 0.052 Uiso 1 1 calc R . . C26 C 0.39225(16) 0.56860(7) 0.59546(16) 0.0430(4) Uani 1 1 d . . . C27 C 0.52276(17) 0.58112(8) 0.58222(18) 0.0560(5) Uani 1 1 d . . . H27 H 0.5446 0.6098 0.5286 0.067 Uiso 1 1 calc R . . C28 C 0.61979(18) 0.55141(8) 0.64786(19) 0.0629(6) Uani 1 1 d . . . H28 H 0.7066 0.5605 0.6392 0.075 Uiso 1 1 calc R . . C29 C 0.58945(18) 0.50841(8) 0.72606(18) 0.0561(5) Uani 1 1 d . . . H29 H 0.6557 0.4880 0.7683 0.067 Uiso 1 1 calc R . . B1 B 0.4841(2) 0.35817(9) 0.9308(2) 0.0486(6) Uani 1 1 d . . . B2 B 0.0487(2) 0.60011(9) 0.4321(2) 0.0503(6) Uani 1 1 d . . . N1 N 0.33612(14) 0.36296(6) 0.97729(13) 0.0473(4) Uani 1 1 d . . . N2 N 0.48802(16) 0.40294(6) 0.82495(17) 0.0534(4) Uani 1 1 d . . . N3 N 0.09876(13) 0.65243(6) 0.35446(13) 0.0454(4) Uani 1 1 d . . . N4 N 0.17805(15) 0.57220(7) 0.48147(16) 0.0531(5) Uani 1 1 d . . . H30 H 0.5401(19) 0.3996(8) 0.7627(19) 0.067(7) Uiso 1 1 d . . . H31 H 0.1849(17) 0.5378(8) 0.4834(17) 0.061(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0732(15) 0.0535(13) 0.0615(14) 0.0133(11) 0.0049(12) -0.0040(11) C3 0.0761(16) 0.0781(17) 0.0678(15) 0.0192(13) 0.0139(13) -0.0125(13) C4 0.0578(13) 0.1033(19) 0.0523(13) 0.0123(13) 0.0108(11) -0.0043(14) C5 0.0534(13) 0.0743(15) 0.0495(12) 0.0053(11) 0.0068(10) 0.0104(11) C6 0.0465(11) 0.0549(13) 0.0374(10) 0.0007(9) -0.0014(9) 0.0051(10) C7 0.0533(12) 0.0430(11) 0.0504(12) 0.0023(9) 0.0045(10) 0.0065(9) C8 0.0426(11) 0.0458(11) 0.0434(11) 0.0011(9) -0.0055(9) 0.0033(9) C9 0.0570(13) 0.0546(12) 0.0620(13) 0.0015(10) -0.0058(10) 0.0078(10) C10 0.0614(15) 0.0813(17) 0.1063(19) 0.0016(14) -0.0101(13) 0.0019(12) C11 0.0774(15) 0.0574(13) 0.0640(14) -0.0058(11) 0.0022(11) 0.0089(11) C12 0.117(2) 0.0883(19) 0.0802(17) -0.0291(14) -0.0083(15) 0.0007(15) C13 0.0604(13) 0.0601(14) 0.0565(13) 0.0041(11) -0.0117(11) 0.0058(10) C14 0.0775(16) 0.0614(14) 0.0617(14) 0.0189(12) -0.0050(12) 0.0134(12) C15 0.0772(16) 0.0514(13) 0.0752(15) 0.0199(12) 0.0111(13) 0.0063(12) C16 0.0587(13) 0.0428(12) 0.0757(15) 0.0115(11) 0.0026(11) -0.0048(10) C17 0.0448(11) 0.0432(11) 0.0508(12) 0.0006(9) 0.0048(9) -0.0023(9) C18 0.0489(11) 0.0440(11) 0.0539(12) 0.0041(9) -0.0095(9) -0.0114(9) C19 0.0417(11) 0.0459(11) 0.0421(11) 0.0027(8) -0.0040(8) -0.0077(9) C20 0.0556(13) 0.0658(14) 0.0632(13) 0.0088(11) 0.0046(10) -0.0118(11) C21 0.0727(16) 0.0824(17) 0.0910(17) 0.0038(13) 0.0193(13) 0.0049(13) C22 0.0526(12) 0.0520(12) 0.0745(14) 0.0042(11) -0.0134(11) -0.0041(10) C23 0.0676(15) 0.0826(17) 0.0854(17) -0.0229(14) -0.0181(13) 0.0084(13) C24 0.0419(11) 0.0450(11) 0.0405(10) 0.0007(9) -0.0019(8) -0.0009(9) C25 0.0391(10) 0.0455(11) 0.0448(11) 0.0005(9) -0.0042(8) -0.0064(9) C26 0.0415(11) 0.0441(11) 0.0425(11) 0.0014(9) -0.0053(8) -0.0049(9) C27 0.0471(12) 0.0631(13) 0.0570(13) 0.0159(10) -0.0012(10) -0.0083(10) C28 0.0377(11) 0.0777(15) 0.0731(14) 0.0206(12) 0.0013(10) -0.0044(10) C29 0.0440(12) 0.0643(13) 0.0591(13) 0.0155(11) -0.0037(9) 0.0041(10) B1 0.0499(13) 0.0459(13) 0.0505(13) 0.0048(11) 0.0056(10) 0.0069(10) B2 0.0456(13) 0.0463(13) 0.0577(14) 0.0088(11) -0.0077(11) -0.0064(10) N1 0.0517(9) 0.0459(10) 0.0439(9) 0.0055(7) -0.0008(7) 0.0032(8) N2 0.0554(10) 0.0542(11) 0.0519(11) 0.0067(8) 0.0128(9) 0.0133(8) N3 0.0456(9) 0.0439(9) 0.0458(9) 0.0040(7) -0.0036(7) 0.0011(7) N4 0.0506(10) 0.0390(10) 0.0673(11) 0.0091(9) -0.0149(8) -0.0077(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 C2 N1 1.353(2) . ? C2 C3 1.357(3) . ? C2 H2 0.9300 . ? C3 C4 1.386(3) . ? C3 H3 0.9300 . ? C4 C5 1.355(3) . ? C4 H4 0.9300 . ? C5 C6 1.410(2) . ? C5 H5 0.9300 . ? C6 N1 1.363(2) . ? C6 C7 1.411(2) . ? C7 C8 1.368(2) . ? C7 H7 0.9300 . ? C8 N2 1.334(2) . ? C8 C24 1.482(2) . ? C9 C10 1.527(3) . ? C9 B1 1.617(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.520(3) . ? C11 B1 1.594(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N3 1.350(2) . ? C13 C14 1.363(3) . ? C13 H13 0.9300 . ? C14 C15 1.387(3) . ? C14 H14 0.9300 . ? C15 C16 1.351(3) . ? C15 H15 0.9300 . ? C16 C17 1.404(2) . ? C16 H16 0.9300 . ? C17 N3 1.371(2) . ? C17 C18 1.417(2) . ? C18 C19 1.365(2) . ? C18 H18 0.9300 . ? C19 N4 1.338(2) . ? C19 C26 1.488(2) . ? C20 C21 1.541(3) . ? C20 B2 1.607(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.501(3) . ? C22 B2 1.601(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.387(2) . ? C24 C29 1.391(2) . ? C25 C26 1.384(2) . ? C25 H25 0.9300 . ? C26 C27 1.392(2) . ? C27 C28 1.377(2) . ? C27 H27 0.9300 . ? C28 C29 1.375(2) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? B1 N2 1.549(3) . ? B1 N1 1.629(2) . ? B2 N4 1.553(3) . ? B2 N3 1.614(2) . ? N2 H30 0.865(19) . ? N4 H31 0.846(18) . ? 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 N1 C2 C3 123.7(2) . . ? N1 C2 H2 118.2 . . ? C3 C2 H2 118.2 . . ? C2 C3 C4 118.3(2) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C5 C4 C3 119.3(2) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 121.3(2) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? N1 C6 C5 118.50(17) . . ? N1 C6 C7 119.43(16) . . ? C5 C6 C7 122.04(18) . . ? C8 C7 C6 122.03(17) . . ? C8 C7 H7 119.0 . . ? C6 C7 H7 119.0 . . ? N2 C8 C7 119.90(17) . . ? N2 C8 C24 119.43(16) . . ? C7 C8 C24 120.64(16) . . ? C10 C9 B1 115.57(17) . . ? C10 C9 H9A 108.4 . . ? B1 C9 H9A 108.4 . . ? C10 C9 H9B 108.4 . . ? B1 C9 H9B 108.4 . . ? H9A C9 H9B 107.4 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 B1 116.71(18) . . ? C12 C11 H11A 108.1 . . ? B1 C11 H11A 108.1 . . ? C12 C11 H11B 108.1 . . ? B1 C11 H11B 108.1 . . ? H11A C11 H11B 107.3 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 C14 122.93(19) . . ? N3 C13 H13 118.5 . . ? C14 C13 H13 118.5 . . ? C13 C14 C15 118.32(19) . . ? C13 C14 H14 120.8 . . ? C15 C14 H14 120.8 . . ? C16 C15 C14 119.75(19) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 121.00(19) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? N3 C17 C16 118.49(17) . . ? N3 C17 C18 119.37(16) . . ? C16 C17 C18 122.07(17) . . ? C19 C18 C17 122.20(16) . . ? C19 C18 H18 118.9 . . ? C17 C18 H18 118.9 . . ? N4 C19 C18 118.82(16) . . ? N4 C19 C26 118.51(16) . . ? C18 C19 C26 122.66(15) . . ? C21 C20 B2 116.36(17) . . ? C21 C20 H20A 108.2 . . ? B2 C20 H20A 108.2 . . ? C21 C20 H20B 108.2 . . ? B2 C20 H20B 108.2 . . ? H20A C20 H20B 107.4 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 B2 117.41(16) . . ? C23 C22 H22A 108.0 . . ? B2 C22 H22A 108.0 . . ? C23 C22 H22B 108.0 . . ? B2 C22 H22B 108.0 . . ? H22A C22 H22B 107.2 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C29 118.76(16) . . ? C25 C24 C8 120.54(16) . . ? C29 C24 C8 120.70(16) . . ? C26 C25 C24 121.71(16) . . ? C26 C25 H25 119.1 . . ? C24 C25 H25 119.1 . . ? C25 C26 C27 118.29(16) . . ? C25 C26 C19 120.19(15) . . ? C27 C26 C19 121.51(16) . . ? C28 C27 C26 120.54(17) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C29 C28 C27 120.57(17) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C28 C29 C24 120.12(17) . . ? C28 C29 H29 119.9 . . ? C24 C29 H29 119.9 . . ? N2 B1 C11 110.39(16) . . ? N2 B1 C9 110.90(16) . . ? C11 B1 C9 114.20(16) . . ? N2 B1 N1 102.83(14) . . ? C11 B1 N1 111.84(16) . . ? C9 B1 N1 106.04(15) . . ? N4 B2 C22 109.52(16) . . ? N4 B2 C20 110.61(16) . . ? C22 B2 C20 112.80(16) . . ? N4 B2 N3 102.63(14) . . ? C22 B2 N3 113.76(15) . . ? C20 B2 N3 107.05(15) . . ? C2 N1 C6 118.90(16) . . ? C2 N1 B1 120.25(16) . . ? C6 N1 B1 120.24(14) . . ? C8 N2 B1 123.87(17) . . ? C8 N2 H30 115.9(13) . . ? B1 N2 H30 119.9(13) . . ? C13 N3 C17 119.28(16) . . ? C13 N3 B2 120.90(15) . . ? C17 N3 B2 119.10(14) . . ? C19 N4 B2 124.11(17) . . ? C19 N4 H31 114.8(13) . . ? B2 N4 H31 121.1(13) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.96 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.134 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.029 #===END data_9 _database_code_depnum_ccdc_archive 'CCDC 871066' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common diethylboronpicoline-14dicyanobenzene _chemical_melting_point ? _chemical_formula_moiety 'C28 H36 B2 N4' _chemical_formula_sum 'C28 H36 B2 N4' _chemical_formula_weight 450.23 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 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 6.7145(4) _cell_length_b 15.9589(9) _cell_length_c 23.1949(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2485.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6923 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 25.40 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9694 _exptl_absorpt_correction_T_max 0.9878 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23210 _diffrn_reflns_av_R_equivalents 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.43 _reflns_number_total 2290 _reflns_number_gt 1796 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0382P)^2^+1.4060P] 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 2290 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 C2 C 0.3346(2) 0.59111(10) 0.32542(6) 0.0184(3) Uani 1 1 d . . . H2 H 0.3900 0.6459 0.3260 0.022 Uiso 1 1 calc R . . C3 C 0.4352(2) 0.52943(10) 0.29653(6) 0.0200(4) Uani 1 1 d . . . H3 H 0.5580 0.5410 0.2777 0.024 Uiso 1 1 calc R . . C4 C 0.3522(2) 0.44867(10) 0.29540(6) 0.0185(3) Uani 1 1 d . . . H4 H 0.4162 0.4048 0.2748 0.022 Uiso 1 1 calc R . . C5 C 0.1787(2) 0.43395(9) 0.32423(6) 0.0181(3) Uani 1 1 d . . . H5 H 0.1238 0.3791 0.3243 0.022 Uiso 1 1 calc R . . C6 C 0.0787(2) 0.49882(9) 0.35410(6) 0.0164(3) Uani 1 1 d . . . C7 C -0.0968(2) 0.48329(9) 0.38611(6) 0.0180(3) Uani 1 1 d . . . H7 H -0.1622 0.4309 0.3819 0.022 Uiso 1 1 calc R . . C8 C -0.1758(2) 0.54184(9) 0.42320(6) 0.0167(3) Uani 1 1 d . . . C9 C -0.0973(2) 0.68933(10) 0.32178(7) 0.0209(4) Uani 1 1 d . . . H9A H -0.0049 0.7055 0.2904 0.025 Uiso 1 1 calc R . . H9B H -0.1789 0.6419 0.3076 0.025 Uiso 1 1 calc R . . C10 C -0.2355(3) 0.76344(11) 0.33432(7) 0.0277(4) Uani 1 1 d . . . H10A H -0.3232 0.7494 0.3667 0.042 Uiso 1 1 calc R . . H10B H -0.3161 0.7755 0.3001 0.042 Uiso 1 1 calc R . . H10C H -0.1556 0.8128 0.3442 0.042 Uiso 1 1 calc R . . C11 C 0.1736(2) 0.72914(9) 0.40423(7) 0.0200(4) Uani 1 1 d . . . H11A H 0.2560 0.7534 0.3730 0.024 Uiso 1 1 calc R . . H11B H 0.0870 0.7744 0.4191 0.024 Uiso 1 1 calc R . . C12 C 0.3124(3) 0.70124(11) 0.45289(8) 0.0281(4) Uani 1 1 d . . . H12A H 0.2330 0.6796 0.4851 0.042 Uiso 1 1 calc R . . H12B H 0.3917 0.7491 0.4660 0.042 Uiso 1 1 calc R . . H12C H 0.4014 0.6571 0.4387 0.042 Uiso 1 1 calc R . . C13 C -0.3399(2) 0.51954(9) 0.46335(6) 0.0166(3) Uani 1 1 d . . . C14 C -0.4915(2) 0.46572(9) 0.44537(6) 0.0171(3) Uani 1 1 d . . . H14 H -0.4861 0.4419 0.4079 0.021 Uiso 1 1 calc R . . C15 C -0.3501(2) 0.55349(9) 0.51864(6) 0.0171(3) Uani 1 1 d . . . H15 H -0.2479 0.5900 0.5317 0.021 Uiso 1 1 calc R . . B1 B 0.0333(3) 0.65739(11) 0.37664(7) 0.0178(4) Uani 1 1 d . . . N1 N 0.15950(18) 0.57776(7) 0.35325(5) 0.0166(3) Uani 1 1 d . . . N2 N -0.1019(2) 0.61982(8) 0.42446(6) 0.0191(3) Uani 1 1 d . . . H1 H -0.156(3) 0.6534(11) 0.4503(8) 0.031(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0188(8) 0.0192(8) 0.0173(8) 0.0012(6) 0.0013(6) -0.0023(6) C3 0.0180(8) 0.0240(9) 0.0179(8) 0.0005(6) 0.0009(6) 0.0000(7) C4 0.0203(8) 0.0202(8) 0.0150(7) -0.0007(6) -0.0009(6) 0.0052(7) C5 0.0201(8) 0.0161(8) 0.0182(8) 0.0011(6) -0.0034(6) 0.0004(6) C6 0.0175(7) 0.0166(7) 0.0151(7) 0.0012(6) -0.0030(6) 0.0008(6) C7 0.0180(8) 0.0159(8) 0.0201(8) -0.0004(6) -0.0003(6) -0.0029(6) C8 0.0160(7) 0.0175(8) 0.0168(7) 0.0014(6) -0.0027(6) -0.0010(6) C9 0.0218(8) 0.0193(8) 0.0218(8) -0.0008(7) 0.0015(7) -0.0005(7) C10 0.0268(9) 0.0243(9) 0.0322(10) 0.0004(8) -0.0022(8) 0.0037(7) C11 0.0215(8) 0.0167(8) 0.0217(8) -0.0010(7) 0.0035(7) 0.0004(6) C12 0.0272(9) 0.0253(9) 0.0316(10) -0.0051(7) -0.0046(7) 0.0003(8) C13 0.0168(8) 0.0151(7) 0.0179(8) 0.0036(6) 0.0003(6) 0.0020(6) C14 0.0198(8) 0.0164(8) 0.0150(7) -0.0003(6) 0.0000(6) 0.0008(6) C15 0.0174(8) 0.0158(8) 0.0182(8) 0.0009(6) -0.0023(6) -0.0018(6) B1 0.0195(9) 0.0141(9) 0.0197(9) -0.0003(7) 0.0030(7) 0.0010(7) N1 0.0175(7) 0.0160(7) 0.0162(6) 0.0005(5) -0.0003(5) 0.0003(5) N2 0.0227(7) 0.0148(7) 0.0197(7) -0.0024(5) 0.0048(6) -0.0007(6) _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 C2 N1 1.3583(19) . ? C2 C3 1.369(2) . ? C2 H2 0.9500 . ? C3 C4 1.405(2) . ? C3 H3 0.9500 . ? C4 C5 1.364(2) . ? C4 H4 0.9500 . ? C5 C6 1.415(2) . ? C5 H5 0.9500 . ? C6 N1 1.3718(19) . ? C6 C7 1.415(2) . ? C7 C8 1.376(2) . ? C7 H7 0.9500 . ? C8 N2 1.340(2) . ? C8 C13 1.486(2) . ? C9 C10 1.531(2) . ? C9 B1 1.627(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.530(2) . ? C11 B1 1.615(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C15 1.394(2) . ? C13 C14 1.396(2) . ? C14 C15 1.386(2) 5_466 ? C14 H14 0.9500 . ? C15 C14 1.386(2) 5_466 ? C15 H15 0.9500 . ? B1 N2 1.554(2) . ? B1 N1 1.621(2) . ? N2 H1 0.881(19) . ? 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 N1 C2 C3 123.16(14) . . ? N1 C2 H2 118.4 . . ? C3 C2 H2 118.4 . . ? C2 C3 C4 118.23(14) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C5 C4 C3 119.22(14) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 121.28(14) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? N1 C6 C7 119.86(13) . . ? N1 C6 C5 118.51(13) . . ? C7 C6 C5 121.59(14) . . ? C8 C7 C6 122.00(14) . . ? C8 C7 H7 119.0 . . ? C6 C7 H7 119.0 . . ? N2 C8 C7 120.10(14) . . ? N2 C8 C13 118.90(14) . . ? C7 C8 C13 120.99(14) . . ? C10 C9 B1 114.83(13) . . ? C10 C9 H9A 108.6 . . ? B1 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? B1 C9 H9B 108.6 . . ? H9A C9 H9B 107.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 B1 116.19(13) . . ? C12 C11 H11A 108.2 . . ? B1 C11 H11A 108.2 . . ? C12 C11 H11B 108.2 . . ? B1 C11 H11B 108.2 . . ? H11A C11 H11B 107.4 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C15 C13 C14 118.59(14) . . ? C15 C13 C8 121.31(14) . . ? C14 C13 C8 120.06(13) . . ? C15 C14 C13 121.04(14) 5_466 . ? C15 C14 H14 119.5 5_466 . ? C13 C14 H14 119.5 . . ? C14 C15 C13 120.37(14) 5_466 . ? C14 C15 H15 119.8 5_466 . ? C13 C15 H15 119.8 . . ? N2 B1 C11 109.37(13) . . ? N2 B1 N1 103.99(12) . . ? C11 B1 N1 112.54(12) . . ? N2 B1 C9 111.36(13) . . ? C11 B1 C9 113.72(13) . . ? N1 B1 C9 105.41(12) . . ? C2 N1 C6 119.56(13) . . ? C2 N1 B1 119.26(12) . . ? C6 N1 B1 120.55(12) . . ? C8 N2 B1 124.00(13) . . ? C8 N2 H1 115.3(12) . . ? B1 N2 H1 119.4(12) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.43 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.219 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.041 #===END data_10 _database_code_depnum_ccdc_archive 'CCDC 871067' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common diethylboronpicoline-benzophenone _chemical_melting_point ? _chemical_formula_moiety 'C23 H26 B N O' _chemical_formula_sum 'C23 H26 B N O' _chemical_formula_weight 343.26 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 Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.6575(5) _cell_length_b 14.9677(9) _cell_length_c 14.9962(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1943.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9875 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 25.43 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.71 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.49 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.173 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9521 _exptl_absorpt_correction_T_max 0.9666 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19784 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0152 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.43 _reflns_number_total 3600 _reflns_number_gt 3475 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+0.3783P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(10) _refine_ls_number_reflns 3600 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0691 _refine_ls_wR_factor_gt 0.0680 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 C2 C 0.07146(14) -0.15309(8) 0.23497(9) 0.0225(3) Uani 1 1 d . . . H2 H -0.0195 -0.1580 0.1999 0.027 Uiso 1 1 calc R . . C3 C 0.14839(15) -0.22985(8) 0.25868(9) 0.0248(3) Uani 1 1 d . . . H3 H 0.1106 -0.2868 0.2413 0.030 Uiso 1 1 calc R . . C4 C 0.28258(15) -0.22211(8) 0.30864(9) 0.0245(3) Uani 1 1 d . . . H4 H 0.3387 -0.2739 0.3259 0.029 Uiso 1 1 calc R . . C5 C 0.33342(15) -0.13828(8) 0.33291(8) 0.0230(3) Uani 1 1 d . . . H5 H 0.4261 -0.1321 0.3663 0.028 Uiso 1 1 calc R . . C6 C 0.24954(14) -0.06259(8) 0.30878(8) 0.0191(2) Uani 1 1 d . . . C7 C 0.29522(14) 0.02831(8) 0.34251(8) 0.0210(3) Uani 1 1 d . . . H7A H 0.4094 0.0314 0.3446 0.025 Uiso 1 1 calc R . . H7B H 0.2570 0.0347 0.4044 0.025 Uiso 1 1 calc R . . C8 C 0.23578(14) 0.10792(8) 0.28758(8) 0.0189(3) Uani 1 1 d . . . C9 C 0.31898(14) 0.12127(8) 0.19822(8) 0.0187(2) Uani 1 1 d . . . C10 C 0.27184(14) 0.19296(8) 0.14507(8) 0.0212(3) Uani 1 1 d . . . H10 H 0.1960 0.2332 0.1671 0.025 Uiso 1 1 calc R . . C11 C 0.33327(15) 0.20660(9) 0.06103(8) 0.0251(3) Uani 1 1 d . . . H11 H 0.2995 0.2557 0.0259 0.030 Uiso 1 1 calc R . . C12 C 0.44463(16) 0.14825(9) 0.02819(9) 0.0278(3) Uani 1 1 d . . . H12 H 0.4863 0.1567 -0.0298 0.033 Uiso 1 1 calc R . . C13 C 0.49433(15) 0.07787(9) 0.08060(9) 0.0268(3) Uani 1 1 d . . . H13 H 0.5706 0.0380 0.0585 0.032 Uiso 1 1 calc R . . C14 C 0.43332(14) 0.06496(8) 0.16573(9) 0.0222(3) Uani 1 1 d . . . H14 H 0.4703 0.0173 0.2017 0.027 Uiso 1 1 calc R . . C15 C 0.25306(14) 0.19162(8) 0.34595(8) 0.0195(3) Uani 1 1 d . . . C16 C 0.14166(16) 0.21101(8) 0.40980(8) 0.0236(3) Uani 1 1 d . . . H16 H 0.0547 0.1729 0.4163 0.028 Uiso 1 1 calc R . . C17 C 0.15621(17) 0.28572(9) 0.46436(9) 0.0290(3) Uani 1 1 d . . . H17 H 0.0788 0.2986 0.5074 0.035 Uiso 1 1 calc R . . C18 C 0.28277(18) 0.34120(9) 0.45621(9) 0.0301(3) Uani 1 1 d . . . H18 H 0.2921 0.3925 0.4932 0.036 Uiso 1 1 calc R . . C19 C 0.39564(17) 0.32195(9) 0.39429(9) 0.0301(3) Uani 1 1 d . . . H19 H 0.4833 0.3597 0.3889 0.036 Uiso 1 1 calc R . . C20 C 0.38131(15) 0.24718(8) 0.33952(9) 0.0254(3) Uani 1 1 d . . . H20 H 0.4600 0.2340 0.2974 0.030 Uiso 1 1 calc R . . C21 C 0.03626(14) 0.01516(8) 0.11564(8) 0.0214(3) Uani 1 1 d . . . H21A H 0.1468 0.0222 0.1003 0.026 Uiso 1 1 calc R . . H21B H 0.0014 -0.0433 0.0923 0.026 Uiso 1 1 calc R . . C22 C -0.05645(15) 0.08958(9) 0.07019(9) 0.0262(3) Uani 1 1 d . . . H22A H -0.1661 0.0830 0.0851 0.039 Uiso 1 1 calc R . . H22B H -0.0431 0.0855 0.0054 0.039 Uiso 1 1 calc R . . H22C H -0.0194 0.1478 0.0910 0.039 Uiso 1 1 calc R . . C23 C -0.16084(14) 0.00143(8) 0.25495(8) 0.0211(3) Uani 1 1 d . . . H23A H -0.2181 0.0575 0.2433 0.025 Uiso 1 1 calc R . . H23B H -0.2072 -0.0457 0.2171 0.025 Uiso 1 1 calc R . . C24 C -0.18489(16) -0.02431(10) 0.35259(9) 0.0302(3) Uani 1 1 d . . . H24A H -0.1587 -0.0875 0.3609 0.045 Uiso 1 1 calc R . . H24B H -0.2932 -0.0145 0.3690 0.045 Uiso 1 1 calc R . . H24C H -0.1183 0.0126 0.3905 0.045 Uiso 1 1 calc R . . B1 B 0.01780(16) 0.01560(9) 0.22410(9) 0.0188(3) Uani 1 1 d . . . N1 N 0.12022(12) -0.07078(6) 0.25965(7) 0.0187(2) Uani 1 1 d . . . O1 O 0.07525(9) 0.09461(5) 0.27262(5) 0.01745(18) 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 C2 0.0221(6) 0.0188(6) 0.0265(6) -0.0010(5) 0.0000(5) -0.0014(5) C3 0.0284(7) 0.0150(6) 0.0309(7) -0.0014(5) 0.0043(6) -0.0018(5) C4 0.0255(6) 0.0180(6) 0.0300(7) 0.0047(5) 0.0044(5) 0.0039(5) C5 0.0221(6) 0.0227(6) 0.0243(6) 0.0033(5) -0.0012(5) 0.0021(5) C6 0.0197(6) 0.0185(6) 0.0191(6) 0.0022(5) 0.0022(5) -0.0005(5) C7 0.0215(6) 0.0185(6) 0.0230(6) -0.0003(5) -0.0045(5) -0.0002(5) C8 0.0174(6) 0.0163(6) 0.0229(6) 0.0000(5) -0.0029(5) -0.0002(5) C9 0.0169(6) 0.0162(6) 0.0229(6) -0.0029(5) -0.0028(5) -0.0036(4) C10 0.0197(6) 0.0181(6) 0.0257(6) -0.0013(5) 0.0002(5) -0.0007(5) C11 0.0264(7) 0.0245(7) 0.0246(6) 0.0025(5) -0.0009(5) -0.0053(5) C12 0.0257(7) 0.0328(7) 0.0249(7) -0.0030(6) 0.0056(5) -0.0073(6) C13 0.0200(6) 0.0270(7) 0.0334(7) -0.0086(6) 0.0044(6) -0.0030(5) C14 0.0179(6) 0.0203(6) 0.0284(7) -0.0018(5) -0.0020(5) -0.0023(5) C15 0.0235(6) 0.0162(6) 0.0187(6) 0.0028(5) -0.0048(5) 0.0002(5) C16 0.0282(7) 0.0197(6) 0.0228(6) -0.0005(5) -0.0013(5) -0.0021(5) C17 0.0393(8) 0.0254(7) 0.0224(6) -0.0022(5) -0.0004(6) 0.0031(6) C18 0.0468(8) 0.0183(6) 0.0253(6) -0.0036(5) -0.0102(6) -0.0009(6) C19 0.0364(7) 0.0215(6) 0.0325(7) 0.0001(5) -0.0094(6) -0.0099(6) C20 0.0268(6) 0.0235(6) 0.0258(7) -0.0006(5) -0.0031(6) -0.0031(5) C21 0.0216(6) 0.0206(6) 0.0221(6) -0.0023(5) -0.0004(5) -0.0025(5) C22 0.0259(7) 0.0315(7) 0.0214(6) 0.0044(5) -0.0034(5) -0.0015(6) C23 0.0205(6) 0.0170(6) 0.0259(6) 0.0000(5) -0.0028(5) -0.0002(5) C24 0.0261(7) 0.0354(7) 0.0291(7) -0.0005(6) 0.0043(6) -0.0011(6) B1 0.0197(6) 0.0147(7) 0.0220(7) 0.0015(5) -0.0017(6) 0.0013(5) N1 0.0199(5) 0.0157(5) 0.0204(5) 0.0003(4) 0.0007(4) -0.0005(4) O1 0.0154(4) 0.0160(4) 0.0209(4) 0.0001(3) -0.0010(3) 0.0001(3) _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 C2 N1 1.3540(15) . ? C2 C3 1.3748(17) . ? C2 H2 0.9500 . ? C3 C4 1.3872(19) . ? C3 H3 0.9500 . ? C4 C5 1.3785(17) . ? C4 H4 0.9500 . ? C5 C6 1.3935(17) . ? C5 H5 0.9500 . ? C6 N1 1.3459(16) . ? C6 C7 1.5045(16) . ? C7 C8 1.5372(16) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O1 1.4218(14) . ? C8 C9 1.5344(17) . ? C8 C15 1.5356(16) . ? C9 C14 1.3884(17) . ? C9 C10 1.3975(17) . ? C10 C11 1.3831(18) . ? C10 H10 0.9500 . ? C11 C12 1.3910(19) . ? C11 H11 0.9500 . ? C12 C13 1.383(2) . ? C12 H12 0.9500 . ? C13 C14 1.3951(19) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.3897(18) . ? C15 C20 1.3906(17) . ? C16 C17 1.3913(18) . ? C16 H16 0.9500 . ? C17 C18 1.380(2) . ? C17 H17 0.9500 . ? C18 C19 1.378(2) . ? C18 H18 0.9500 . ? C19 C20 1.3938(18) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.5329(18) . ? C21 B1 1.6344(18) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.5283(18) . ? C23 B1 1.6282(18) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? B1 O1 1.4749(16) . ? B1 N1 1.6558(16) . ? 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 N1 C2 C3 122.59(11) . . ? N1 C2 H2 118.7 . . ? C3 C2 H2 118.7 . . ? C2 C3 C4 118.40(11) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 119.08(11) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 120.33(12) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? N1 C6 C5 120.11(11) . . ? N1 C6 C7 119.01(10) . . ? C5 C6 C7 120.73(11) . . ? C6 C7 C8 115.65(10) . . ? C6 C7 H7A 108.4 . . ? C8 C7 H7A 108.4 . . ? C6 C7 H7B 108.4 . . ? C8 C7 H7B 108.4 . . ? H7A C7 H7B 107.4 . . ? O1 C8 C9 109.84(9) . . ? O1 C8 C15 107.43(10) . . ? C9 C8 C15 110.24(9) . . ? O1 C8 C7 107.65(9) . . ? C9 C8 C7 114.31(10) . . ? C15 C8 C7 107.11(9) . . ? C14 C9 C10 118.30(11) . . ? C14 C9 C8 124.20(11) . . ? C10 C9 C8 117.45(11) . . ? C11 C10 C9 121.39(12) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 119.76(12) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C13 C12 C11 119.52(12) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.52(12) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C9 C14 C13 120.46(12) . . ? C9 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C20 118.49(11) . . ? C16 C15 C8 119.71(11) . . ? C20 C15 C8 121.74(11) . . ? C15 C16 C17 120.68(12) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C18 C17 C16 120.22(13) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C19 C18 C17 119.78(12) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C20 120.11(13) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C15 C20 C19 120.69(13) . . ? C15 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 B1 112.85(10) . . ? C22 C21 H21A 109.0 . . ? B1 C21 H21A 109.0 . . ? C22 C21 H21B 109.0 . . ? B1 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 B1 115.76(11) . . ? C24 C23 H23A 108.3 . . ? B1 C23 H23A 108.3 . . ? C24 C23 H23B 108.3 . . ? B1 C23 H23B 108.3 . . ? H23A C23 H23B 107.4 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O1 B1 C23 106.53(10) . . ? O1 B1 C21 117.47(10) . . ? C23 B1 C21 112.03(10) . . ? O1 B1 N1 106.66(9) . . ? C23 B1 N1 108.39(9) . . ? C21 B1 N1 105.36(10) . . ? C6 N1 C2 119.46(10) . . ? C6 N1 B1 123.41(9) . . ? C2 N1 B1 117.10(10) . . ? C8 O1 B1 121.32(9) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.43 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.167 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.030 #===END data_11 _database_code_depnum_ccdc_archive 'CCDC 871068' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common diethylboronpicoline-2chloroacetophenone _chemical_melting_point ? _chemical_formula_moiety 'C18 H23 B Cl N O' _chemical_formula_sum 'C18 H23 B Cl N O' _chemical_formula_weight 315.63 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.2474(6) _cell_length_b 18.4202(13) _cell_length_c 11.0654(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.8910(10) _cell_angle_gamma 90.00 _cell_volume 1665.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9066 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 25.30 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8463 _exptl_absorpt_correction_T_max 0.9533 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16385 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.33 _reflns_number_total 3030 _reflns_number_gt 2617 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+0.7761P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3030 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0879 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 C2 C 0.69619(19) 0.39671(9) 0.63366(14) 0.0226(3) Uani 1 1 d . . . H2 H 0.6374 0.4079 0.5559 0.027 Uiso 1 1 calc R . . C3 C 0.86152(19) 0.38458(9) 0.64300(15) 0.0239(4) Uani 1 1 d . . . H3 H 0.9163 0.3884 0.5731 0.029 Uiso 1 1 calc R . . C4 C 0.94759(19) 0.36674(8) 0.75522(15) 0.0231(3) Uani 1 1 d . . . H4 H 1.0618 0.3572 0.7637 0.028 Uiso 1 1 calc R . . C5 C 0.86340(18) 0.36321(9) 0.85474(15) 0.0227(3) Uani 1 1 d . . . H5 H 0.9198 0.3504 0.9325 0.027 Uiso 1 1 calc R . . C6 C 0.69713(18) 0.37830(8) 0.84191(14) 0.0190(3) Uani 1 1 d . . . C7 C 0.60360(18) 0.38204(9) 0.94836(14) 0.0204(3) Uani 1 1 d . . . H7A H 0.5948 0.4335 0.9727 0.024 Uiso 1 1 calc R . . H7B H 0.6656 0.3558 1.0180 0.024 Uiso 1 1 calc R . . C8 C 0.43022(18) 0.34943(8) 0.92204(13) 0.0180(3) Uani 1 1 d . . . C9 C 0.34122(18) 0.36578(8) 1.03129(14) 0.0187(3) Uani 1 1 d . . . C10 C 0.22488(19) 0.42050(9) 1.02543(14) 0.0222(3) Uani 1 1 d . . . H10 H 0.1989 0.4475 0.9522 0.027 Uiso 1 1 calc R . . C11 C 0.1459(2) 0.43627(10) 1.12538(15) 0.0281(4) Uani 1 1 d . . . H11 H 0.0660 0.4737 1.1197 0.034 Uiso 1 1 calc R . . C12 C 0.1826(2) 0.39799(10) 1.23289(16) 0.0317(4) Uani 1 1 d . . . H12 H 0.1275 0.4084 1.3008 0.038 Uiso 1 1 calc R . . C13 C 0.3007(2) 0.34429(10) 1.24029(16) 0.0334(4) Uani 1 1 d . . . H13 H 0.3281 0.3181 1.3143 0.040 Uiso 1 1 calc R . . C14 C 0.3792(2) 0.32834(9) 1.14092(14) 0.0267(4) Uani 1 1 d . . . H14 H 0.4602 0.2913 1.1475 0.032 Uiso 1 1 calc R . . C15 C 0.44505(19) 0.26727(8) 0.90360(15) 0.0219(3) Uani 1 1 d . . . H15A H 0.5089 0.2455 0.9770 0.026 Uiso 1 1 calc R . . H15B H 0.5043 0.2579 0.8332 0.026 Uiso 1 1 calc R . . C16 C 0.4054(2) 0.49944(9) 0.71330(17) 0.0281(4) Uani 1 1 d . . . H16A H 0.4614 0.5181 0.7920 0.034 Uiso 1 1 calc R . . H16B H 0.4630 0.5192 0.6476 0.034 Uiso 1 1 calc R . . C17 C 0.2278(2) 0.52657(10) 0.6946(2) 0.0416(5) Uani 1 1 d . . . H17A H 0.1758 0.5136 0.6125 0.062 Uiso 1 1 calc R . . H17B H 0.2265 0.5795 0.7042 0.062 Uiso 1 1 calc R . . H17C H 0.1676 0.5040 0.7553 0.062 Uiso 1 1 calc R . . C18 C 0.33367(19) 0.37408(10) 0.58740(14) 0.0274(4) Uani 1 1 d . . . H18A H 0.2143 0.3832 0.5788 0.033 Uiso 1 1 calc R . . H18B H 0.3758 0.3983 0.5182 0.033 Uiso 1 1 calc R . . C19 C 0.3607(2) 0.29238(10) 0.57656(16) 0.0332(4) Uani 1 1 d . . . H19A H 0.4779 0.2826 0.5793 0.050 Uiso 1 1 calc R . . H19B H 0.3020 0.2748 0.4991 0.050 Uiso 1 1 calc R . . H19C H 0.3195 0.2674 0.6444 0.050 Uiso 1 1 calc R . . B1 B 0.4181(2) 0.41204(10) 0.71293(16) 0.0197(4) Uani 1 1 d . . . N1 N 0.61418(15) 0.39337(7) 0.73081(11) 0.0190(3) Uani 1 1 d . . . O1 O 0.34461(12) 0.38015(6) 0.81609(9) 0.0183(2) Uani 1 1 d . . . Cl1 Cl 0.24641(5) 0.22573(2) 0.87678(4) 0.02685(13) 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 C2 0.0197(8) 0.0286(9) 0.0197(8) -0.0018(7) 0.0032(6) -0.0025(7) C3 0.0193(8) 0.0283(9) 0.0253(9) -0.0044(7) 0.0068(7) -0.0033(7) C4 0.0145(7) 0.0222(8) 0.0329(9) -0.0028(7) 0.0045(7) -0.0006(6) C5 0.0185(8) 0.0233(8) 0.0252(8) 0.0010(7) -0.0008(6) -0.0012(6) C6 0.0175(8) 0.0185(8) 0.0204(8) -0.0014(6) 0.0006(6) -0.0024(6) C7 0.0178(8) 0.0238(8) 0.0187(8) -0.0001(6) -0.0005(6) 0.0004(6) C8 0.0162(7) 0.0214(8) 0.0158(7) 0.0007(6) 0.0001(6) 0.0011(6) C9 0.0181(8) 0.0192(8) 0.0189(8) -0.0021(6) 0.0025(6) -0.0045(6) C10 0.0207(8) 0.0245(8) 0.0211(8) -0.0017(6) 0.0015(6) -0.0004(6) C11 0.0222(8) 0.0327(9) 0.0298(9) -0.0081(7) 0.0049(7) 0.0013(7) C12 0.0320(9) 0.0427(11) 0.0227(9) -0.0080(8) 0.0117(7) -0.0058(8) C13 0.0447(11) 0.0369(10) 0.0197(8) 0.0030(7) 0.0082(8) -0.0032(8) C14 0.0323(9) 0.0250(9) 0.0229(8) 0.0011(7) 0.0039(7) 0.0022(7) C15 0.0205(8) 0.0227(8) 0.0221(8) -0.0009(6) 0.0013(6) -0.0002(6) C16 0.0225(8) 0.0272(9) 0.0357(9) 0.0091(7) 0.0076(7) 0.0008(7) C17 0.0324(10) 0.0301(10) 0.0650(14) 0.0209(9) 0.0166(9) 0.0099(8) C18 0.0148(8) 0.0483(11) 0.0192(8) 0.0020(7) 0.0030(6) -0.0035(7) C19 0.0331(10) 0.0449(11) 0.0217(9) -0.0069(8) 0.0036(7) -0.0137(8) B1 0.0127(8) 0.0269(9) 0.0198(9) 0.0035(7) 0.0034(7) 0.0010(7) N1 0.0154(6) 0.0215(7) 0.0202(7) -0.0011(5) 0.0027(5) -0.0017(5) O1 0.0145(5) 0.0243(6) 0.0161(5) 0.0036(4) 0.0015(4) 0.0015(4) Cl1 0.0292(2) 0.0226(2) 0.0283(2) -0.00068(16) 0.00238(16) -0.00653(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 C2 N1 1.348(2) . ? C2 C3 1.372(2) . ? C2 H2 0.9500 . ? C3 C4 1.383(2) . ? C3 H3 0.9500 . ? C4 C5 1.382(2) . ? C4 H4 0.9500 . ? C5 C6 1.387(2) . ? C5 H5 0.9500 . ? C6 N1 1.351(2) . ? C6 C7 1.496(2) . ? C7 C8 1.541(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O1 1.4021(17) . ? C8 C9 1.528(2) . ? C8 C15 1.534(2) . ? C9 C10 1.387(2) . ? C9 C14 1.393(2) . ? C10 C11 1.389(2) . ? C10 H10 0.9500 . ? C11 C12 1.380(3) . ? C11 H11 0.9500 . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 C14 1.382(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 Cl1 1.7956(16) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.535(2) . ? C16 B1 1.613(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.528(3) . ? C18 B1 1.624(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? B1 O1 1.4848(19) . ? B1 N1 1.639(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C3 122.34(15) . . ? N1 C2 H2 118.8 . . ? C3 C2 H2 118.8 . . ? C2 C3 C4 119.27(15) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 118.35(14) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? C4 C5 C6 120.45(15) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? N1 C6 C5 120.29(14) . . ? N1 C6 C7 117.10(13) . . ? C5 C6 C7 122.55(14) . . ? C6 C7 C8 113.49(12) . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? O1 C8 C9 109.91(12) . . ? O1 C8 C15 109.10(12) . . ? C9 C8 C15 110.82(12) . . ? O1 C8 C7 110.38(12) . . ? C9 C8 C7 107.92(12) . . ? C15 C8 C7 108.71(12) . . ? C10 C9 C14 118.16(14) . . ? C10 C9 C8 120.71(14) . . ? C14 C9 C8 121.08(14) . . ? C9 C10 C11 120.78(15) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 120.53(16) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 119.07(15) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C14 C13 C12 120.54(16) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C9 120.90(16) . . ? C13 C14 H14 119.5 . . ? C9 C14 H14 119.5 . . ? C8 C15 Cl1 110.78(11) . . ? C8 C15 H15A 109.5 . . ? Cl1 C15 H15A 109.5 . . ? C8 C15 H15B 109.5 . . ? Cl1 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C17 C16 B1 112.66(14) . . ? C17 C16 H16A 109.1 . . ? B1 C16 H16A 109.1 . . ? C17 C16 H16B 109.1 . . ? B1 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 B1 116.18(14) . . ? C19 C18 H18A 108.2 . . ? B1 C18 H18A 108.2 . . ? C19 C18 H18B 108.2 . . ? B1 C18 H18B 108.2 . . ? H18A C18 H18B 107.4 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O1 B1 C16 111.08(13) . . ? O1 B1 C18 108.36(13) . . ? C16 B1 C18 114.31(14) . . ? O1 B1 N1 108.92(12) . . ? C16 B1 N1 105.79(12) . . ? C18 B1 N1 108.23(12) . . ? C2 N1 C6 119.22(13) . . ? C2 N1 B1 119.29(12) . . ? C6 N1 B1 121.41(12) . . ? C8 O1 B1 126.21(11) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.273 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.042 #===END data_12 _database_code_depnum_ccdc_archive 'CCDC 871069' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common diethylboronpicoline-4Chlorobenzaldehyde _chemical_melting_point ? _chemical_formula_moiety 'C17 H21 B Cl N O' _chemical_formula_sum 'C17 H21 B Cl N O' _chemical_formula_weight 301.61 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 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' _cell_length_a 13.0246(11) _cell_length_b 7.6223(7) _cell_length_c 16.3135(14) _cell_angle_alpha 90.00 _cell_angle_beta 91.5070(10) _cell_angle_gamma 90.00 _cell_volume 1619.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6169 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 25.62 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8961 _exptl_absorpt_correction_T_max 0.9083 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7921 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 25.66 _reflns_number_total 3038 _reflns_number_gt 2890 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0522P)^2^+0.6976P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(5) _refine_ls_number_reflns 3038 _refine_ls_number_parameters 192 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0874 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.983 _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 C2 C 0.13247(17) -0.1755(3) 0.70203(14) 0.0364(5) Uani 1 1 d . . . H2 H 0.1193 -0.1620 0.6448 0.044 Uiso 1 1 calc R . . C3 C 0.08643(19) -0.3111(3) 0.74242(17) 0.0450(6) Uani 1 1 d . . . H3 H 0.0414 -0.3892 0.7137 0.054 Uiso 1 1 calc R . . C4 C 0.1063(2) -0.3324(3) 0.82491(18) 0.0506(6) Uani 1 1 d . . . H4 H 0.0761 -0.4265 0.8539 0.061 Uiso 1 1 calc R . . C5 C 0.1709(2) -0.2152(3) 0.86508(17) 0.0458(6) Uani 1 1 d . . . H5 H 0.1851 -0.2283 0.9222 0.055 Uiso 1 1 calc R . . C6 C 0.21520(17) -0.0776(3) 0.82223(12) 0.0324(4) Uani 1 1 d . . . C7 C 0.28242(18) 0.0560(3) 0.86529(13) 0.0364(5) Uani 1 1 d . . . H7A H 0.3528 0.0081 0.8721 0.044 Uiso 1 1 calc R . . H7B H 0.2558 0.0784 0.9206 0.044 Uiso 1 1 calc R . . C8 C 0.28669(16) 0.2284(3) 0.81826(12) 0.0300(4) Uani 1 1 d . . . H8 H 0.2154 0.2765 0.8136 0.036 Uiso 1 1 calc R . . C9 C 0.35467(15) 0.3666(3) 0.85869(13) 0.0293(4) Uani 1 1 d . . . C10 C 0.36387(18) 0.3833(3) 0.94380(13) 0.0389(5) Uani 1 1 d . . . H10 H 0.3278 0.3043 0.9777 0.047 Uiso 1 1 calc R . . C11 C 0.42461(18) 0.5128(3) 0.97998(13) 0.0409(5) Uani 1 1 d . . . H11 H 0.4306 0.5223 1.0380 0.049 Uiso 1 1 calc R . . C12 C 0.47601(15) 0.6272(3) 0.93025(12) 0.0309(4) Uani 1 1 d . . . C13 C 0.46674(16) 0.6166(3) 0.84590(12) 0.0317(4) Uani 1 1 d . . . H13 H 0.5012 0.6983 0.8123 0.038 Uiso 1 1 calc R . . C14 C 0.40649(15) 0.4852(3) 0.81072(11) 0.0301(4) Uani 1 1 d . . . H14 H 0.4007 0.4765 0.7527 0.036 Uiso 1 1 calc R . . C15 C 0.15285(16) 0.2199(3) 0.65146(13) 0.0347(5) Uani 1 1 d . . . H15A H 0.1061 0.1478 0.6165 0.042 Uiso 1 1 calc R . . H15B H 0.1136 0.2622 0.6987 0.042 Uiso 1 1 calc R . . C16 C 0.18923(18) 0.3766(3) 0.60242(14) 0.0408(5) Uani 1 1 d . . . H16A H 0.2306 0.3357 0.5569 0.061 Uiso 1 1 calc R . . H16B H 0.2309 0.4535 0.6381 0.061 Uiso 1 1 calc R . . H16C H 0.1296 0.4418 0.5807 0.061 Uiso 1 1 calc R . . C17 C 0.31079(15) 0.0050(3) 0.61262(12) 0.0323(4) Uani 1 1 d . . . H17A H 0.2609 -0.0427 0.5716 0.039 Uiso 1 1 calc R . . H17B H 0.3519 0.0956 0.5849 0.039 Uiso 1 1 calc R . . C18 C 0.38227(17) -0.1423(3) 0.64058(15) 0.0396(5) Uani 1 1 d . . . H18A H 0.3415 -0.2452 0.6553 0.059 Uiso 1 1 calc R . . H18B H 0.4233 -0.1036 0.6884 0.059 Uiso 1 1 calc R . . H18C H 0.4280 -0.1731 0.5960 0.059 Uiso 1 1 calc R . . B1 B 0.24776(16) 0.0983(3) 0.68493(13) 0.0264(4) Uani 1 1 d . . . N1 N 0.19612(12) -0.0600(2) 0.74106(10) 0.0278(4) Uani 1 1 d . . . O1 O 0.31984(10) 0.19219(17) 0.73880(7) 0.0274(3) Uani 1 1 d . . . Cl1 Cl 0.55342(4) 0.79001(7) 0.97542(3) 0.04176(16) 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 C2 0.0359(11) 0.0304(11) 0.0431(12) -0.0066(9) 0.0046(9) -0.0039(9) C3 0.0455(13) 0.0311(12) 0.0588(15) -0.0098(11) 0.0100(11) -0.0086(10) C4 0.0585(15) 0.0246(11) 0.0695(17) 0.0059(11) 0.0149(13) -0.0058(11) C5 0.0619(16) 0.0317(12) 0.0439(12) 0.0101(10) 0.0019(11) -0.0009(11) C6 0.0423(11) 0.0236(10) 0.0314(11) 0.0040(8) 0.0029(9) 0.0014(8) C7 0.0534(13) 0.0297(11) 0.0257(10) 0.0040(9) -0.0052(9) -0.0031(10) C8 0.0348(11) 0.0304(10) 0.0249(10) 0.0014(8) 0.0025(8) 0.0019(8) C9 0.0315(10) 0.0297(10) 0.0268(9) 0.0023(8) 0.0022(8) 0.0024(9) C10 0.0486(13) 0.0444(12) 0.0238(10) 0.0006(9) 0.0004(9) -0.0130(11) C11 0.0508(14) 0.0466(14) 0.0251(11) 0.0003(10) -0.0003(9) -0.0120(11) C12 0.0361(11) 0.0279(11) 0.0285(10) -0.0038(8) -0.0026(8) -0.0028(8) C13 0.0398(11) 0.0266(10) 0.0289(10) 0.0037(8) 0.0033(9) -0.0032(9) C14 0.0412(12) 0.0302(10) 0.0189(9) 0.0000(8) -0.0004(8) 0.0009(9) C15 0.0314(10) 0.0378(12) 0.0346(11) 0.0034(9) -0.0054(8) 0.0039(9) C16 0.0496(13) 0.0384(12) 0.0342(11) 0.0071(9) -0.0024(9) 0.0090(10) C17 0.0309(10) 0.0355(12) 0.0306(10) -0.0052(9) 0.0016(8) -0.0016(9) C18 0.0363(11) 0.0377(12) 0.0449(13) -0.0114(10) 0.0015(10) 0.0016(9) B1 0.0275(10) 0.0269(11) 0.0250(11) 0.0022(9) 0.0018(8) -0.0009(9) N1 0.0286(8) 0.0241(8) 0.0308(8) -0.0023(6) 0.0035(7) 0.0016(6) O1 0.0343(7) 0.0269(7) 0.0210(7) -0.0005(5) 0.0013(5) -0.0017(6) Cl1 0.0546(3) 0.0377(3) 0.0326(3) -0.0027(2) -0.0051(2) -0.0160(3) _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 C2 N1 1.357(3) . ? C2 C3 1.372(3) . ? C2 H2 0.9500 . ? C3 C4 1.373(4) . ? C3 H3 0.9500 . ? C4 C5 1.380(4) . ? C4 H4 0.9500 . ? C5 C6 1.394(3) . ? C5 H5 0.9500 . ? C6 N1 1.348(3) . ? C6 C7 1.505(3) . ? C7 C8 1.523(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O1 1.404(2) . ? C8 C9 1.516(3) . ? C8 H8 1.0000 . ? C9 C14 1.383(3) . ? C9 C10 1.396(3) . ? C10 C11 1.387(3) . ? C10 H10 0.9500 . ? C11 C12 1.377(3) . ? C11 H11 0.9500 . ? C12 C13 1.380(3) . ? C12 Cl1 1.749(2) . ? C13 C14 1.387(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.521(3) . ? C15 B1 1.628(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.521(3) . ? C17 B1 1.619(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? B1 O1 1.457(3) . ? B1 N1 1.667(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 N1 C2 C3 122.2(2) . . ? N1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C2 C3 C4 119.1(2) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 C5 119.1(2) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C4 C5 C6 120.3(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? N1 C6 C5 120.0(2) . . ? N1 C6 C7 118.75(18) . . ? C5 C6 C7 121.2(2) . . ? C6 C7 C8 112.16(17) . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? O1 C8 C9 110.35(16) . . ? O1 C8 C7 108.17(17) . . ? C9 C8 C7 114.13(16) . . ? O1 C8 H8 108.0 . . ? C9 C8 H8 108.0 . . ? C7 C8 H8 108.0 . . ? C14 C9 C10 118.20(19) . . ? C14 C9 C8 119.75(18) . . ? C10 C9 C8 122.00(18) . . ? C11 C10 C9 121.4(2) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C12 C11 C10 118.74(19) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C11 C12 C13 121.26(19) . . ? C11 C12 Cl1 119.01(15) . . ? C13 C12 Cl1 119.72(16) . . ? C12 C13 C14 119.24(18) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C9 C14 C13 121.13(18) . . ? C9 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C16 C15 B1 112.30(17) . . ? C16 C15 H15A 109.1 . . ? B1 C15 H15A 109.1 . . ? C16 C15 H15B 109.1 . . ? B1 C15 H15B 109.1 . . ? H15A C15 H15B 107.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 B1 115.06(17) . . ? C18 C17 H17A 108.5 . . ? B1 C17 H17A 108.5 . . ? C18 C17 H17B 108.5 . . ? B1 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O1 B1 C17 108.91(15) . . ? O1 B1 C15 113.21(16) . . ? C17 B1 C15 113.62(16) . . ? O1 B1 N1 106.68(15) . . ? C17 B1 N1 107.60(15) . . ? C15 B1 N1 106.40(15) . . ? C6 N1 C2 119.41(18) . . ? C6 N1 B1 123.06(16) . . ? C2 N1 B1 117.53(16) . . ? C8 O1 B1 116.38(15) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.66 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.240 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.037 #===END data_13 _database_code_depnum_ccdc_archive 'CCDC 871070' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common diethylboronpicoline-4nitrobenzaldehyde _chemical_melting_point ? _chemical_formula_moiety 'C17 H21 B N2 O3' _chemical_formula_sum 'C17 H21 B N2 O3' _chemical_formula_weight 312.17 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 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.2247(10) _cell_length_b 16.0450(18) _cell_length_c 10.9529(12) _cell_angle_alpha 90.00 _cell_angle_beta 93.9990(10) _cell_angle_gamma 90.00 _cell_volume 1617.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9961 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 25.37 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.44 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9448 _exptl_absorpt_correction_T_max 0.9627 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15678 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.37 _reflns_number_total 2963 _reflns_number_gt 2581 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0553P)^2^+3.8017P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2963 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1454 _refine_ls_wR_factor_gt 0.1399 _refine_ls_goodness_of_fit_ref 0.902 _refine_ls_restrained_S_all 0.902 _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 C2 C 0.1923(2) -0.07366(14) 0.8944(2) 0.0216(5) Uani 1 1 d . . . H2 H 0.1695 -0.0436 0.9653 0.026 Uiso 1 1 calc R . . C3 C 0.2151(3) -0.15783(14) 0.9044(2) 0.0243(5) Uani 1 1 d . . . H3 H 0.2045 -0.1858 0.9797 0.029 Uiso 1 1 calc R . . C4 C 0.2539(3) -0.20119(14) 0.8022(2) 0.0256(5) Uani 1 1 d . . . H4 H 0.2752 -0.2591 0.8070 0.031 Uiso 1 1 calc R . . C5 C 0.2608(3) -0.15844(14) 0.6933(2) 0.0251(5) Uani 1 1 d . . . H5 H 0.2856 -0.1874 0.6221 0.030 Uiso 1 1 calc R . . C6 C 0.2319(2) -0.07355(14) 0.6868(2) 0.0202(5) Uani 1 1 d . . . C7 C 0.2281(3) -0.02692(14) 0.5674(2) 0.0258(5) Uani 1 1 d . . . H7A H 0.1290 -0.0304 0.5269 0.031 Uiso 1 1 calc R . . H7B H 0.2956 -0.0540 0.5132 0.031 Uiso 1 1 calc R . . C8 C 0.2701(3) 0.06421(15) 0.5836(2) 0.0258(5) Uani 1 1 d . . . H8 H 0.3744 0.0674 0.6148 0.031 Uiso 1 1 calc R . . C9 C 0.2510(3) 0.11198(14) 0.4636(2) 0.0247(5) Uani 1 1 d . . . C10 C 0.1295(3) 0.16186(14) 0.4360(2) 0.0243(5) Uani 1 1 d . . . H10 H 0.0541 0.1638 0.4908 0.029 Uiso 1 1 calc R . . C11 C 0.1175(3) 0.20895(15) 0.3290(2) 0.0249(5) Uani 1 1 d . . . H11 H 0.0347 0.2429 0.3097 0.030 Uiso 1 1 calc R . . C12 C 0.2296(3) 0.20476(14) 0.2517(2) 0.0230(5) Uani 1 1 d . . . C13 C 0.3494(3) 0.15460(17) 0.2753(2) 0.0328(6) Uani 1 1 d . . . H13 H 0.4239 0.1522 0.2197 0.039 Uiso 1 1 calc R . . C14 C 0.3589(3) 0.10784(17) 0.3816(2) 0.0337(6) Uani 1 1 d . . . H14 H 0.4403 0.0724 0.3987 0.040 Uiso 1 1 calc R . . C15 C 0.3313(3) 0.09974(14) 0.8826(2) 0.0254(5) Uani 1 1 d . . . H15A H 0.3339 0.1614 0.8821 0.031 Uiso 1 1 calc R . . H15B H 0.3141 0.0824 0.9672 0.031 Uiso 1 1 calc R . . C16 C 0.4824(3) 0.06908(17) 0.8556(2) 0.0341(6) Uani 1 1 d . . . H16A H 0.4829 0.0080 0.8534 0.051 Uiso 1 1 calc R . . H16B H 0.5536 0.0886 0.9199 0.051 Uiso 1 1 calc R . . H16C H 0.5077 0.0909 0.7763 0.051 Uiso 1 1 calc R . . C17 C 0.0393(3) 0.09736(15) 0.8507(2) 0.0241(5) Uani 1 1 d . . . H17A H 0.0429 0.0799 0.9375 0.029 Uiso 1 1 calc R . . H17B H 0.0316 0.1589 0.8488 0.029 Uiso 1 1 calc R . . C18 C -0.0977(3) 0.06103(17) 0.7851(2) 0.0322(6) Uani 1 1 d . . . H18A H -0.1000 0.0750 0.6979 0.048 Uiso 1 1 calc R . . H18B H -0.1835 0.0844 0.8204 0.048 Uiso 1 1 calc R . . H18C H -0.0974 0.0003 0.7948 0.048 Uiso 1 1 calc R . . B1 B 0.1903(3) 0.07102(15) 0.7951(2) 0.0201(5) Uani 1 1 d . . . N1 N 0.2009(2) -0.03155(11) 0.78869(16) 0.0179(4) Uani 1 1 d . . . N2 N 0.2229(2) 0.25807(13) 0.14171(18) 0.0283(5) Uani 1 1 d . . . O1 O 0.18560(18) 0.10136(9) 0.66851(14) 0.0233(4) Uani 1 1 d . . . O2 O 0.1086(2) 0.29359(13) 0.11158(17) 0.0425(5) Uani 1 1 d . . . O3 O 0.3341(2) 0.26502(12) 0.08698(16) 0.0364(5) 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 C2 0.0272(12) 0.0225(11) 0.0155(11) 0.0005(9) 0.0040(9) -0.0012(9) C3 0.0328(13) 0.0224(12) 0.0177(11) 0.0050(9) 0.0009(9) -0.0013(10) C4 0.0353(14) 0.0162(11) 0.0243(12) 0.0004(9) -0.0044(10) 0.0001(9) C5 0.0375(14) 0.0194(11) 0.0183(11) -0.0031(9) 0.0013(10) 0.0019(10) C6 0.0272(12) 0.0184(11) 0.0152(10) -0.0009(8) 0.0011(9) -0.0017(9) C7 0.0411(14) 0.0212(12) 0.0154(11) -0.0003(9) 0.0041(10) 0.0040(10) C8 0.0354(14) 0.0241(12) 0.0183(11) 0.0005(9) 0.0048(10) 0.0045(10) C9 0.0374(14) 0.0195(11) 0.0174(11) -0.0006(9) 0.0038(10) 0.0002(10) C10 0.0315(13) 0.0230(12) 0.0191(11) -0.0004(9) 0.0073(9) -0.0025(10) C11 0.0296(13) 0.0238(12) 0.0212(12) 0.0022(9) 0.0010(9) 0.0003(10) C12 0.0333(13) 0.0218(11) 0.0139(10) 0.0021(9) 0.0008(9) -0.0056(10) C13 0.0377(15) 0.0393(15) 0.0227(12) 0.0076(11) 0.0117(11) 0.0055(12) C14 0.0399(15) 0.0367(14) 0.0252(13) 0.0076(11) 0.0079(11) 0.0119(12) C15 0.0375(14) 0.0184(11) 0.0205(11) -0.0004(9) 0.0025(10) -0.0014(10) C16 0.0308(14) 0.0395(15) 0.0309(14) 0.0001(11) -0.0047(11) -0.0039(11) C17 0.0316(13) 0.0224(12) 0.0189(11) 0.0026(9) 0.0052(9) 0.0061(10) C18 0.0315(14) 0.0404(15) 0.0253(13) 0.0015(11) 0.0053(10) 0.0035(11) B1 0.0287(14) 0.0149(12) 0.0172(12) 0.0015(9) 0.0045(10) 0.0028(10) N1 0.0209(9) 0.0176(9) 0.0155(9) 0.0002(7) 0.0029(7) -0.0003(7) N2 0.0411(13) 0.0255(11) 0.0183(10) 0.0028(8) 0.0009(9) -0.0012(9) O1 0.0380(10) 0.0173(8) 0.0154(8) 0.0004(6) 0.0084(7) 0.0028(7) O2 0.0517(13) 0.0476(12) 0.0279(10) 0.0151(9) -0.0009(9) 0.0098(10) O3 0.0488(12) 0.0386(11) 0.0235(9) 0.0071(8) 0.0147(8) -0.0058(9) _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 C2 N1 1.348(3) . ? C2 C3 1.370(3) . ? C2 H2 0.9500 . ? C3 C4 1.386(3) . ? C3 H3 0.9500 . ? C4 C5 1.381(3) . ? C4 H4 0.9500 . ? C5 C6 1.389(3) . ? C5 H5 0.9500 . ? C6 N1 1.351(3) . ? C6 C7 1.505(3) . ? C7 C8 1.520(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O1 1.389(3) . ? C8 C9 1.521(3) . ? C8 H8 1.0000 . ? C9 C14 1.387(4) . ? C9 C10 1.393(3) . ? C10 C11 1.392(3) . ? C10 H10 0.9500 . ? C11 C12 1.383(3) . ? C11 H11 0.9500 . ? C12 C13 1.377(4) . ? C12 N2 1.475(3) . ? C13 C14 1.383(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.526(4) . ? C15 B1 1.628(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.525(4) . ? C17 B1 1.616(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? B1 O1 1.467(3) . ? B1 N1 1.650(3) . ? N2 O2 1.224(3) . ? N2 O3 1.229(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 N1 C2 C3 123.0(2) . . ? N1 C2 H2 118.5 . . ? C3 C2 H2 118.5 . . ? C2 C3 C4 118.5(2) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 118.6(2) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C6 120.7(2) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? N1 C6 C5 119.9(2) . . ? N1 C6 C7 118.43(19) . . ? C5 C6 C7 121.7(2) . . ? C6 C7 C8 112.77(19) . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? O1 C8 C7 109.91(19) . . ? O1 C8 C9 109.03(19) . . ? C7 C8 C9 111.79(19) . . ? O1 C8 H8 108.7 . . ? C7 C8 H8 108.7 . . ? C9 C8 H8 108.7 . . ? C14 C9 C10 119.3(2) . . ? C14 C9 C8 119.3(2) . . ? C10 C9 C8 121.3(2) . . ? C11 C10 C9 120.7(2) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 118.0(2) . . ? C12 C11 H11 121.0 . . ? C10 C11 H11 121.0 . . ? C13 C12 C11 122.6(2) . . ? C13 C12 N2 118.6(2) . . ? C11 C12 N2 118.8(2) . . ? C12 C13 C14 118.5(2) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C13 C14 C9 120.9(2) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? C16 C15 B1 119.8(2) . . ? C16 C15 H15A 107.4 . . ? B1 C15 H15A 107.4 . . ? C16 C15 H15B 107.4 . . ? B1 C15 H15B 107.4 . . ? H15A C15 H15B 106.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 B1 115.5(2) . . ? C18 C17 H17A 108.4 . . ? B1 C17 H17A 108.4 . . ? C18 C17 H17B 108.4 . . ? B1 C17 H17B 108.4 . . ? H17A C17 H17B 107.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O1 B1 C17 107.45(19) . . ? O1 B1 C15 115.64(19) . . ? C17 B1 C15 112.23(19) . . ? O1 B1 N1 106.80(17) . . ? C17 B1 N1 109.37(18) . . ? C15 B1 N1 105.09(18) . . ? C2 N1 C6 119.20(19) . . ? C2 N1 B1 117.17(17) . . ? C6 N1 B1 123.28(17) . . ? O2 N2 O3 124.0(2) . . ? O2 N2 C12 118.4(2) . . ? O3 N2 C12 117.5(2) . . ? C8 O1 B1 120.63(18) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.588 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.064 #===END data_14 _database_code_depnum_ccdc_archive 'CCDC 871071' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common diethylboronpicoline-4trifluorotolualdehyde _chemical_melting_point ? _chemical_formula_moiety 'C18 H21 B F3 N O' _chemical_formula_sum 'C18 H21 B F3 N O' _chemical_formula_weight 335.17 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3937(6) _cell_length_b 10.2137(7) _cell_length_c 11.2380(12) _cell_angle_alpha 108.6650(10) _cell_angle_beta 102.6990(10) _cell_angle_gamma 100.7820(10) _cell_volume 855.21(12) _cell_formula_units_Z 2 _cell_measurement_temperature 109(2) _cell_measurement_reflns_used 6127 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 25.44 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9306 _exptl_absorpt_correction_T_max 0.9654 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 109(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8665 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.45 _reflns_number_total 3139 _reflns_number_gt 2752 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.2881P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3139 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0928 _refine_ls_wR_factor_gt 0.0891 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 C2 C 0.58623(17) -0.26010(14) 0.56330(14) 0.0275(3) Uani 1 1 d . . . H2 H 0.5065 -0.3434 0.4952 0.033 Uiso 1 1 calc R . . C3 C 0.75654(17) -0.24637(15) 0.58135(14) 0.0303(3) Uani 1 1 d . . . H3 H 0.7937 -0.3192 0.5271 0.036 Uiso 1 1 calc R . . C4 C 0.87342(17) -0.12476(15) 0.67990(14) 0.0283(3) Uani 1 1 d . . . H4 H 0.9921 -0.1120 0.6941 0.034 Uiso 1 1 calc R . . C5 C 0.81339(16) -0.02260(15) 0.75689(13) 0.0258(3) Uani 1 1 d . . . H5 H 0.8914 0.0613 0.8254 0.031 Uiso 1 1 calc R . . C6 C 0.63934(16) -0.04139(13) 0.73501(12) 0.0220(3) Uani 1 1 d . . . C7 C 0.57346(16) 0.06992(14) 0.81887(13) 0.0254(3) Uani 1 1 d . . . H7A H 0.6487 0.1667 0.8406 0.031 Uiso 1 1 calc R . . H7B H 0.5780 0.0557 0.9025 0.031 Uiso 1 1 calc R . . C8 C 0.39099(16) 0.06386(13) 0.75190(13) 0.0230(3) Uani 1 1 d . . . H8 H 0.3880 0.0913 0.6738 0.028 Uiso 1 1 calc R . . C9 C 0.32753(15) 0.16660(14) 0.84806(12) 0.0227(3) Uani 1 1 d . . . C10 C 0.26105(17) 0.12403(14) 0.93718(13) 0.0273(3) Uani 1 1 d . . . H10 H 0.2515 0.0290 0.9349 0.033 Uiso 1 1 calc R . . C11 C 0.20880(17) 0.21887(15) 1.02916(13) 0.0286(3) Uani 1 1 d . . . H11 H 0.1642 0.1891 1.0900 0.034 Uiso 1 1 calc R . . C12 C 0.22171(16) 0.35748(14) 1.03242(13) 0.0256(3) Uani 1 1 d . . . C13 C 0.28577(17) 0.40057(14) 0.94337(13) 0.0286(3) Uani 1 1 d . . . H13 H 0.2937 0.4951 0.9449 0.034 Uiso 1 1 calc R . . C14 C 0.33840(17) 0.30471(14) 0.85172(13) 0.0268(3) Uani 1 1 d . . . H14 H 0.3825 0.3345 0.7907 0.032 Uiso 1 1 calc R . . C15 C 0.17190(19) 0.45910(16) 1.13663(14) 0.0334(3) Uani 1 1 d . . . C16 C 0.23475(16) -0.34282(14) 0.60190(13) 0.0254(3) Uani 1 1 d . . . H16A H 0.1121 -0.3544 0.5913 0.030 Uiso 1 1 calc R . . H16B H 0.2445 -0.4174 0.5241 0.030 Uiso 1 1 calc R . . C17 C 0.31278(18) -0.37120(16) 0.72435(15) 0.0342(3) Uani 1 1 d . . . H17A H 0.4300 -0.3743 0.7292 0.051 Uiso 1 1 calc R . . H17B H 0.2459 -0.4635 0.7192 0.051 Uiso 1 1 calc R . . H17C H 0.3125 -0.2940 0.8031 0.051 Uiso 1 1 calc R . . C18 C 0.26232(16) -0.16962(14) 0.46136(12) 0.0247(3) Uani 1 1 d . . . H18A H 0.3129 -0.0688 0.4734 0.030 Uiso 1 1 calc R . . H18B H 0.3094 -0.2321 0.3994 0.030 Uiso 1 1 calc R . . C19 C 0.06967(17) -0.20844(17) 0.40054(14) 0.0335(3) Uani 1 1 d . . . H19A H 0.0181 -0.3072 0.3906 0.050 Uiso 1 1 calc R . . H19B H 0.0445 -0.2010 0.3140 0.050 Uiso 1 1 calc R . . H19C H 0.0230 -0.1421 0.4580 0.050 Uiso 1 1 calc R . . B1 B 0.31762(17) -0.18684(15) 0.60203(14) 0.0219(3) Uani 1 1 d . . . N1 N 0.52753(13) -0.15980(11) 0.63861(10) 0.0218(2) Uani 1 1 d . . . O1 O 0.28861(10) -0.07732(9) 0.71061(8) 0.0220(2) Uani 1 1 d . . . F1 F 0.02139(14) 0.40138(11) 1.14667(11) 0.0556(3) Uani 1 1 d . . . F2 F 0.16165(12) 0.58024(9) 1.11835(9) 0.0410(2) Uani 1 1 d . . . F3 F 0.28426(15) 0.49845(12) 1.25614(9) 0.0626(3) 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 C2 0.0258(7) 0.0228(7) 0.0325(7) 0.0061(6) 0.0124(6) 0.0068(5) C3 0.0292(7) 0.0293(7) 0.0389(8) 0.0128(6) 0.0183(6) 0.0135(6) C4 0.0208(6) 0.0357(8) 0.0367(8) 0.0185(6) 0.0136(6) 0.0118(6) C5 0.0204(6) 0.0278(7) 0.0291(7) 0.0116(6) 0.0070(5) 0.0056(5) C6 0.0208(6) 0.0223(6) 0.0249(6) 0.0105(5) 0.0078(5) 0.0064(5) C7 0.0200(6) 0.0233(7) 0.0273(7) 0.0038(5) 0.0052(5) 0.0054(5) C8 0.0217(6) 0.0216(6) 0.0239(6) 0.0068(5) 0.0061(5) 0.0058(5) C9 0.0173(6) 0.0245(7) 0.0213(6) 0.0045(5) 0.0019(5) 0.0060(5) C10 0.0303(7) 0.0234(7) 0.0276(7) 0.0085(6) 0.0068(6) 0.0102(6) C11 0.0310(7) 0.0322(7) 0.0237(7) 0.0099(6) 0.0094(6) 0.0111(6) C12 0.0220(6) 0.0276(7) 0.0220(6) 0.0040(5) 0.0023(5) 0.0100(5) C13 0.0308(7) 0.0232(7) 0.0307(7) 0.0074(6) 0.0080(6) 0.0113(6) C14 0.0265(7) 0.0270(7) 0.0272(7) 0.0094(6) 0.0087(5) 0.0083(6) C15 0.0373(8) 0.0344(8) 0.0277(7) 0.0068(6) 0.0098(6) 0.0167(7) C16 0.0222(6) 0.0227(7) 0.0288(7) 0.0052(5) 0.0101(5) 0.0056(5) C17 0.0318(8) 0.0309(8) 0.0426(9) 0.0186(7) 0.0109(6) 0.0070(6) C18 0.0231(7) 0.0236(6) 0.0240(7) 0.0047(5) 0.0086(5) 0.0045(5) C19 0.0268(7) 0.0406(8) 0.0309(7) 0.0158(6) 0.0053(6) 0.0043(6) B1 0.0162(7) 0.0227(7) 0.0246(7) 0.0053(6) 0.0072(6) 0.0053(6) N1 0.0204(5) 0.0208(5) 0.0257(6) 0.0084(5) 0.0092(4) 0.0069(4) O1 0.0181(4) 0.0203(4) 0.0247(5) 0.0043(4) 0.0076(4) 0.0048(3) F1 0.0637(7) 0.0483(6) 0.0710(7) 0.0183(5) 0.0489(6) 0.0258(5) F2 0.0527(6) 0.0308(5) 0.0411(5) 0.0066(4) 0.0183(4) 0.0221(4) F3 0.0854(8) 0.0698(7) 0.0233(5) -0.0024(5) 0.0038(5) 0.0504(6) _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 C2 N1 1.3512(16) . ? C2 C3 1.3725(19) . ? C3 C4 1.385(2) . ? C4 C5 1.3790(19) . ? C5 C6 1.3923(18) . ? C6 N1 1.3441(17) . ? C6 C7 1.5051(17) . ? C7 C8 1.5310(17) . ? C8 O1 1.4020(15) . ? C8 C9 1.5130(17) . ? C9 C14 1.3831(18) . ? C9 C10 1.3918(19) . ? C10 C11 1.3844(18) . ? C11 C12 1.3874(19) . ? C12 C13 1.3836(19) . ? C12 C15 1.4910(18) . ? C13 C14 1.3896(19) . ? C15 F2 1.3325(17) . ? C15 F1 1.3352(18) . ? C15 F3 1.3455(17) . ? C16 C17 1.529(2) . ? C16 B1 1.6141(19) . ? C18 C19 1.5297(18) . ? C18 B1 1.6221(19) . ? B1 O1 1.4691(16) . ? B1 N1 1.6663(16) . ? 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 N1 C2 C3 122.58(13) . . ? C2 C3 C4 118.99(12) . . ? C5 C4 C3 118.39(12) . . ? C4 C5 C6 120.56(13) . . ? N1 C6 C5 120.33(12) . . ? N1 C6 C7 119.00(11) . . ? C5 C6 C7 120.67(12) . . ? C6 C7 C8 113.12(11) . . ? O1 C8 C9 110.06(10) . . ? O1 C8 C7 108.38(10) . . ? C9 C8 C7 109.73(10) . . ? C14 C9 C10 118.88(12) . . ? C14 C9 C8 121.08(11) . . ? C10 C9 C8 120.01(11) . . ? C11 C10 C9 120.60(12) . . ? C10 C11 C12 119.90(12) . . ? C13 C12 C11 120.04(12) . . ? C13 C12 C15 121.34(12) . . ? C11 C12 C15 118.57(12) . . ? C12 C13 C14 119.61(12) . . ? C9 C14 C13 120.95(12) . . ? F2 C15 F1 106.30(11) . . ? F2 C15 F3 106.49(12) . . ? F1 C15 F3 105.81(13) . . ? F2 C15 C12 113.77(12) . . ? F1 C15 C12 112.65(12) . . ? F3 C15 C12 111.28(11) . . ? C17 C16 B1 115.79(11) . . ? C19 C18 B1 113.42(11) . . ? O1 B1 C16 107.99(10) . . ? O1 B1 C18 114.20(11) . . ? C16 B1 C18 115.28(11) . . ? O1 B1 N1 106.13(10) . . ? C16 B1 N1 108.02(10) . . ? C18 B1 N1 104.62(10) . . ? C6 N1 C2 119.16(11) . . ? C6 N1 B1 123.21(10) . . ? C2 N1 B1 117.58(10) . . ? C8 O1 B1 116.56(9) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.45 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.291 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.036 #===END data_15 _database_code_depnum_ccdc_archive 'CCDC 871072' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common diethylboronpicoline-crotonaldehyde _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 B N O' _chemical_formula_sum 'C14 H22 B N O' _chemical_formula_weight 231.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.2346(10) _cell_length_b 8.4490(10) _cell_length_c 20.337(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.733(2) _cell_angle_gamma 90.00 _cell_volume 1394.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5477 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 25.33 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.101 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9635 _exptl_absorpt_correction_T_max 0.9802 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13186 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2553 _reflns_number_gt 1862 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0233P)^2^+0.6644P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2553 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 C2 C 0.3504(2) 0.8510(2) 0.17011(9) 0.0303(4) Uani 1 1 d . . . H2 H 0.3318 0.8564 0.2149 0.036 Uiso 1 1 calc R . . C3 C 0.5079(2) 0.8692(2) 0.15808(9) 0.0336(5) Uani 1 1 d . . . H3 H 0.5960 0.8890 0.1937 0.040 Uiso 1 1 calc R . . C4 C 0.5365(2) 0.8585(2) 0.09311(9) 0.0311(4) Uani 1 1 d . . . H4 H 0.6447 0.8692 0.0832 0.037 Uiso 1 1 calc R . . C5 C 0.4040(2) 0.8319(2) 0.04308(9) 0.0280(4) Uani 1 1 d . . . H5 H 0.4212 0.8245 -0.0018 0.034 Uiso 1 1 calc R . . C6 C 0.2457(2) 0.81572(19) 0.05736(8) 0.0228(4) Uani 1 1 d . . . C7 C 0.1020(2) 0.7915(2) 0.00184(8) 0.0251(4) Uani 1 1 d . . . H7A H 0.1346 0.7150 -0.0304 0.030 Uiso 1 1 calc R . . H7B H 0.0771 0.8933 -0.0219 0.030 Uiso 1 1 calc R . . C8 C -0.0542(2) 0.73153(19) 0.02432(8) 0.0239(4) Uani 1 1 d . . . H8 H -0.0378 0.6185 0.0385 0.029 Uiso 1 1 calc R . . C9 C -0.2006(2) 0.7422(2) -0.03025(8) 0.0268(4) Uani 1 1 d . . . H9 H -0.2228 0.8416 -0.0517 0.032 Uiso 1 1 calc R . . C10 C -0.3008(2) 0.6241(2) -0.05072(9) 0.0308(4) Uani 1 1 d . . . H10 H -0.2777 0.5258 -0.0284 0.037 Uiso 1 1 calc R . . C11 C -0.4469(2) 0.6286(3) -0.10529(10) 0.0430(5) Uani 1 1 d . . . H11A H -0.4580 0.7349 -0.1249 0.065 Uiso 1 1 calc R . . H11B H -0.5465 0.6026 -0.0870 0.065 Uiso 1 1 calc R . . H11C H -0.4323 0.5514 -0.1398 0.065 Uiso 1 1 calc R . . C12 C 0.0405(2) 0.6096(2) 0.16695(9) 0.0299(4) Uani 1 1 d . . . H12A H 0.0930 0.5434 0.1363 0.036 Uiso 1 1 calc R . . H12B H 0.1088 0.6028 0.2119 0.036 Uiso 1 1 calc R . . C13 C -0.1313(2) 0.5446(2) 0.16994(10) 0.0392(5) Uani 1 1 d . . . H13A H -0.1795 0.6030 0.2036 0.059 Uiso 1 1 calc R . . H13B H -0.1232 0.4322 0.1819 0.059 Uiso 1 1 calc R . . H13C H -0.2015 0.5570 0.1263 0.059 Uiso 1 1 calc R . . C14 C 0.0008(2) 0.9148(2) 0.19830(8) 0.0290(4) Uani 1 1 d . . . H14A H -0.1006 0.8805 0.2144 0.035 Uiso 1 1 calc R . . H14B H 0.0928 0.9058 0.2364 0.035 Uiso 1 1 calc R . . C15 C -0.0187(3) 1.0889(2) 0.17901(10) 0.0459(6) Uani 1 1 d . . . H15A H 0.0837 1.1278 0.1663 0.069 Uiso 1 1 calc R . . H15B H -0.0433 1.1501 0.2171 0.069 Uiso 1 1 calc R . . H15C H -0.1092 1.1007 0.1413 0.069 Uiso 1 1 calc R . . B1 B 0.0349(2) 0.7928(2) 0.14154(10) 0.0246(4) Uani 1 1 d . . . N1 N 0.22008(16) 0.82542(16) 0.12113(7) 0.0242(3) Uani 1 1 d . . . O1 O -0.08156(13) 0.82326(13) 0.07988(5) 0.0233(3) 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 C2 0.0311(10) 0.0325(11) 0.0266(10) -0.0022(8) 0.0033(8) 0.0035(8) C3 0.0269(10) 0.0361(11) 0.0359(11) -0.0031(9) 0.0000(8) 0.0020(8) C4 0.0262(9) 0.0277(10) 0.0408(11) -0.0013(8) 0.0091(8) 0.0014(8) C5 0.0319(10) 0.0226(9) 0.0310(10) 0.0001(8) 0.0101(8) 0.0035(8) C6 0.0278(9) 0.0156(8) 0.0255(9) 0.0008(7) 0.0063(7) 0.0037(7) C7 0.0298(9) 0.0228(9) 0.0236(9) -0.0013(7) 0.0072(8) 0.0049(7) C8 0.0293(9) 0.0189(9) 0.0239(9) -0.0026(7) 0.0054(7) 0.0040(7) C9 0.0297(10) 0.0255(10) 0.0254(9) -0.0015(8) 0.0057(7) 0.0041(8) C10 0.0335(10) 0.0310(10) 0.0281(10) -0.0049(8) 0.0058(8) 0.0017(8) C11 0.0402(11) 0.0496(13) 0.0377(12) -0.0143(10) 0.0021(9) -0.0038(10) C12 0.0328(10) 0.0286(10) 0.0281(10) 0.0040(8) 0.0050(8) 0.0044(8) C13 0.0426(12) 0.0290(11) 0.0469(12) 0.0091(9) 0.0099(10) -0.0008(9) C14 0.0272(9) 0.0347(11) 0.0250(9) -0.0004(8) 0.0046(8) 0.0029(8) C15 0.0757(15) 0.0309(11) 0.0328(11) -0.0078(9) 0.0139(11) 0.0056(11) B1 0.0219(10) 0.0281(11) 0.0245(11) 0.0010(8) 0.0061(8) 0.0024(8) N1 0.0262(8) 0.0214(8) 0.0250(8) 0.0000(6) 0.0045(6) 0.0038(6) O1 0.0260(6) 0.0219(6) 0.0222(6) -0.0017(5) 0.0049(5) 0.0031(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 C2 N1 1.352(2) . ? C2 C3 1.368(2) . ? C2 H2 0.9500 . ? C3 C4 1.384(2) . ? C3 H3 0.9500 . ? C4 C5 1.378(2) . ? C4 H4 0.9500 . ? C5 C6 1.389(2) . ? C5 H5 0.9500 . ? C6 N1 1.351(2) . ? C6 C7 1.505(2) . ? C7 C8 1.523(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O1 1.4193(18) . ? C8 C9 1.497(2) . ? C8 H8 1.0000 . ? C9 C10 1.317(2) . ? C9 H9 0.9500 . ? C10 C11 1.493(2) . ? C10 H10 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.528(2) . ? C12 B1 1.630(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.524(3) . ? C14 B1 1.607(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? B1 O1 1.467(2) . ? B1 N1 1.670(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C3 122.97(17) . . ? N1 C2 H2 118.5 . . ? C3 C2 H2 118.5 . . ? C2 C3 C4 118.87(17) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 118.31(16) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? C4 C5 C6 121.00(17) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? N1 C6 C5 119.93(15) . . ? N1 C6 C7 119.86(14) . . ? C5 C6 C7 120.19(15) . . ? C6 C7 C8 114.64(14) . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7B 108.6 . . ? C8 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? O1 C8 C9 109.95(13) . . ? O1 C8 C7 108.24(13) . . ? C9 C8 C7 111.88(14) . . ? O1 C8 H8 108.9 . . ? C9 C8 H8 108.9 . . ? C7 C8 H8 108.9 . . ? C10 C9 C8 124.87(17) . . ? C10 C9 H9 117.6 . . ? C8 C9 H9 117.6 . . ? C9 C10 C11 126.78(18) . . ? C9 C10 H10 116.6 . . ? C11 C10 H10 116.6 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 B1 112.16(14) . . ? C13 C12 H12A 109.2 . . ? B1 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? B1 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 B1 117.23(15) . . ? C15 C14 H14A 108.0 . . ? B1 C14 H14A 108.0 . . ? C15 C14 H14B 108.0 . . ? B1 C14 H14B 108.0 . . ? H14A C14 H14B 107.2 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O1 B1 C14 109.48(14) . . ? O1 B1 C12 114.63(15) . . ? C14 B1 C12 112.34(14) . . ? O1 B1 N1 104.55(13) . . ? C14 B1 N1 110.52(14) . . ? C12 B1 N1 104.92(13) . . ? C6 N1 C2 118.91(15) . . ? C6 N1 B1 121.74(13) . . ? C2 N1 B1 119.18(14) . . ? C8 O1 B1 114.59(12) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.249 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.038 #===END data_20 _database_code_depnum_ccdc_archive 'CCDC 871073' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common BBNpicoline-n,n-dimethylacetamide _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 B N O' _chemical_formula_sum 'C16 H22 B N O' _chemical_formula_weight 255.16 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 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.4677(4) _cell_length_b 11.4989(5) _cell_length_c 14.4240(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.5030(10) _cell_angle_gamma 90.00 _cell_volume 1376.24(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9502 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 25.37 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.62 _exptl_crystal_size_min 0.47 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9511 _exptl_absorpt_correction_T_max 0.9658 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13509 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0137 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.39 _reflns_number_total 2526 _reflns_number_gt 2268 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.7586P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2526 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0879 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.003 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 C2 C 0.22058(14) 0.89985(11) 0.27875(8) 0.0220(3) Uani 1 1 d . . . H2 H 0.3124 0.8597 0.3124 0.026 Uiso 1 1 calc R . . C3 C 0.15475(15) 0.98712(12) 0.32400(9) 0.0275(3) Uani 1 1 d . . . H3 H 0.1992 1.0061 0.3880 0.033 Uiso 1 1 calc R . . C4 C 0.02194(15) 1.04717(12) 0.27438(10) 0.0291(3) Uani 1 1 d . . . H4 H -0.0227 1.1103 0.3030 0.035 Uiso 1 1 calc R . . C5 C -0.04380(15) 1.01389(11) 0.18336(10) 0.0259(3) Uani 1 1 d . . . H5 H -0.1355 1.0537 0.1492 0.031 Uiso 1 1 calc R . . C6 C 0.02306(14) 0.92168(11) 0.14039(9) 0.0204(3) Uani 1 1 d . . . C7 C -0.05271(14) 0.87508(11) 0.05034(9) 0.0224(3) Uani 1 1 d . . . H7 H -0.1349 0.9185 0.0107 0.027 Uiso 1 1 calc R . . C8 C -0.00928(14) 0.77059(11) 0.02090(8) 0.0210(3) Uani 1 1 d . . . C9 C -0.10268(16) 0.70749(12) -0.06296(9) 0.0293(3) Uani 1 1 d . . . H9A H -0.0393 0.7043 -0.1128 0.044 Uiso 1 1 calc R . . H9B H -0.2042 0.7485 -0.0866 0.044 Uiso 1 1 calc R . . H9C H -0.1258 0.6283 -0.0445 0.044 Uiso 1 1 calc R . . C10 C 0.35520(14) 0.85834(10) 0.06755(8) 0.0172(3) Uani 1 1 d . . . H10 H 0.2816 0.9179 0.0314 0.021 Uiso 1 1 calc R . . C11 C 0.49334(14) 0.92190(10) 0.13348(8) 0.0200(3) Uani 1 1 d . . . H11A H 0.5536 0.9683 0.0942 0.024 Uiso 1 1 calc R . . H11B H 0.4463 0.9769 0.1733 0.024 Uiso 1 1 calc R . . C12 C 0.61259(14) 0.84251(11) 0.19840(8) 0.0218(3) Uani 1 1 d . . . H12A H 0.6784 0.8909 0.2484 0.026 Uiso 1 1 calc R . . H12B H 0.6865 0.8078 0.1608 0.026 Uiso 1 1 calc R . . C13 C 0.53564(14) 0.74340(11) 0.24618(8) 0.0200(3) Uani 1 1 d . . . H13A H 0.5127 0.7733 0.3065 0.024 Uiso 1 1 calc R . . H13B H 0.6162 0.6804 0.2621 0.024 Uiso 1 1 calc R . . C14 C 0.37859(14) 0.68963(10) 0.18871(8) 0.0179(3) Uani 1 1 d . . . H14 H 0.3228 0.6459 0.2328 0.021 Uiso 1 1 calc R . . C15 C 0.41869(15) 0.60429(10) 0.11353(9) 0.0217(3) Uani 1 1 d . . . H15A H 0.4931 0.5438 0.1458 0.026 Uiso 1 1 calc R . . H15B H 0.3183 0.5651 0.0818 0.026 Uiso 1 1 calc R . . C16 C 0.49612(16) 0.66383(11) 0.03803(9) 0.0238(3) Uani 1 1 d . . . H16A H 0.4971 0.6080 -0.0141 0.029 Uiso 1 1 calc R . . H16B H 0.6096 0.6825 0.0665 0.029 Uiso 1 1 calc R . . C17 C 0.41146(15) 0.77609(10) -0.00399(8) 0.0217(3) Uani 1 1 d . . . H17A H 0.3164 0.7542 -0.0528 0.026 Uiso 1 1 calc R . . H17B H 0.4862 0.8195 -0.0361 0.026 Uiso 1 1 calc R . . B1 B 0.25364(15) 0.78182(12) 0.12929(9) 0.0170(3) Uani 1 1 d . . . N1 N 0.16011(11) 0.86883(9) 0.18847(7) 0.0179(2) Uani 1 1 d . . . O1 O 0.11889(9) 0.71383(7) 0.06750(6) 0.0205(2) 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 C2 0.0194(6) 0.0269(6) 0.0199(6) 0.0002(5) 0.0041(5) -0.0030(5) C3 0.0253(6) 0.0346(7) 0.0239(6) -0.0090(5) 0.0083(5) -0.0067(6) C4 0.0239(6) 0.0291(7) 0.0372(8) -0.0104(6) 0.0132(6) -0.0027(6) C5 0.0194(6) 0.0255(7) 0.0340(7) -0.0013(5) 0.0080(5) 0.0024(5) C6 0.0165(6) 0.0213(6) 0.0242(6) 0.0028(5) 0.0062(5) -0.0011(5) C7 0.0174(6) 0.0267(7) 0.0222(6) 0.0034(5) 0.0017(5) 0.0035(5) C8 0.0162(6) 0.0265(6) 0.0197(6) 0.0036(5) 0.0022(5) -0.0004(5) C9 0.0238(6) 0.0344(7) 0.0267(7) -0.0041(6) -0.0022(5) 0.0007(6) C10 0.0191(6) 0.0162(6) 0.0160(5) 0.0021(4) 0.0031(4) 0.0028(4) C11 0.0217(6) 0.0179(6) 0.0217(6) 0.0001(5) 0.0074(5) -0.0026(5) C12 0.0182(6) 0.0249(6) 0.0217(6) -0.0008(5) 0.0028(5) -0.0040(5) C13 0.0177(6) 0.0235(6) 0.0177(6) 0.0023(5) 0.0013(5) 0.0004(5) C14 0.0174(6) 0.0187(6) 0.0173(6) 0.0036(5) 0.0031(5) -0.0020(5) C15 0.0225(6) 0.0161(6) 0.0248(6) 0.0014(5) 0.0012(5) 0.0022(5) C16 0.0292(7) 0.0206(6) 0.0224(6) -0.0028(5) 0.0072(5) 0.0045(5) C17 0.0268(6) 0.0221(6) 0.0169(6) 0.0005(5) 0.0062(5) 0.0021(5) B1 0.0160(6) 0.0185(6) 0.0161(6) -0.0004(5) 0.0020(5) -0.0004(5) N1 0.0161(5) 0.0192(5) 0.0188(5) 0.0012(4) 0.0046(4) -0.0021(4) O1 0.0181(4) 0.0203(4) 0.0214(4) 0.0007(3) -0.0001(3) -0.0001(3) _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 C2 N1 1.3489(15) . ? C2 C3 1.3743(18) . ? C2 H2 0.9500 . ? C3 C4 1.3903(19) . ? C3 H3 0.9500 . ? C4 C5 1.3742(19) . ? C4 H4 0.9500 . ? C5 C6 1.4032(17) . ? C5 H5 0.9500 . ? C6 N1 1.3696(15) . ? C6 C7 1.4331(17) . ? C7 C8 1.3496(18) . ? C7 H7 0.9500 . ? C8 O1 1.3284(14) . ? C8 C9 1.4945(17) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.5372(16) . ? C10 C17 1.5435(16) . ? C10 B1 1.6162(17) . ? C10 H10 1.0000 . ? C11 C12 1.5339(17) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.5418(16) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.5487(16) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.5496(16) . ? C14 B1 1.6174(17) . ? C14 H14 1.0000 . ? C15 C16 1.5392(17) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.5409(17) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? B1 O1 1.5172(15) . ? B1 N1 1.6206(16) . ? 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 N1 C2 C3 122.67(12) . . ? N1 C2 H2 118.7 . . ? C3 C2 H2 118.7 . . ? C2 C3 C4 118.77(12) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 119.04(12) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 120.67(12) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? N1 C6 C5 119.17(11) . . ? N1 C6 C7 118.29(11) . . ? C5 C6 C7 122.39(11) . . ? C8 C7 C6 121.14(11) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? O1 C8 C7 121.64(11) . . ? O1 C8 C9 114.71(11) . . ? C7 C8 C9 123.60(11) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C17 114.00(10) . . ? C11 C10 B1 109.93(9) . . ? C17 C10 B1 107.69(9) . . ? C11 C10 H10 108.4 . . ? C17 C10 H10 108.4 . . ? B1 C10 H10 108.4 . . ? C12 C11 C10 114.95(10) . . ? C12 C11 H11A 108.5 . . ? C10 C11 H11A 108.5 . . ? C12 C11 H11B 108.5 . . ? C10 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? C11 C12 C13 115.30(10) . . ? C11 C12 H12A 108.4 . . ? C13 C12 H12A 108.4 . . ? C11 C12 H12B 108.4 . . ? C13 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C12 C13 C14 116.76(9) . . ? C12 C13 H13A 108.1 . . ? C14 C13 H13A 108.1 . . ? C12 C13 H13B 108.1 . . ? C14 C13 H13B 108.1 . . ? H13A C13 H13B 107.3 . . ? C15 C14 C13 110.04(9) . . ? C15 C14 B1 104.82(9) . . ? C13 C14 B1 115.03(10) . . ? C15 C14 H14 108.9 . . ? C13 C14 H14 108.9 . . ? B1 C14 H14 108.9 . . ? C16 C15 C14 113.40(10) . . ? C16 C15 H15A 108.9 . . ? C14 C15 H15A 108.9 . . ? C16 C15 H15B 108.9 . . ? C14 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C15 C16 C17 114.86(10) . . ? C15 C16 H16A 108.6 . . ? C17 C16 H16A 108.6 . . ? C15 C16 H16B 108.6 . . ? C17 C16 H16B 108.6 . . ? H16A C16 H16B 107.5 . . ? C16 C17 C10 115.59(10) . . ? C16 C17 H17A 108.4 . . ? C10 C17 H17A 108.4 . . ? C16 C17 H17B 108.4 . . ? C10 C17 H17B 108.4 . . ? H17A C17 H17B 107.4 . . ? O1 B1 C10 112.17(9) . . ? O1 B1 C14 108.02(9) . . ? C10 B1 C14 106.56(9) . . ? O1 B1 N1 103.78(8) . . ? C10 B1 N1 108.89(9) . . ? C14 B1 N1 117.54(9) . . ? C2 N1 C6 119.45(10) . . ? C2 N1 B1 122.71(10) . . ? C6 N1 B1 117.45(9) . . ? C8 O1 B1 119.13(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.323 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.036 #===END data_21 _database_code_depnum_ccdc_archive 'CCDC 871074' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common diphenylboronpicoline-acetonitrile _chemical_melting_point ? _chemical_formula_moiety 'C20 H19 B N2, C H2 Cl2' _chemical_formula_sum 'C21 H21 B Cl2 N2' _chemical_formula_weight 383.11 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.5949(7) _cell_length_b 7.6737(5) _cell_length_c 24.2686(16) _cell_angle_alpha 90.00 _cell_angle_beta 100.5870(10) _cell_angle_gamma 90.00 _cell_volume 1939.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8251 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 25.20 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.46 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.342 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8189 _exptl_absorpt_correction_T_max 0.8598 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18411 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.23 _reflns_number_total 3506 _reflns_number_gt 2725 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+1.1158P] 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 3506 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0894 _refine_ls_wR_factor_gt 0.0806 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 C2 C 0.38018(18) 0.2203(3) 0.29023(8) 0.0247(5) Uani 1 1 d . . . H2 H 0.3392 0.1129 0.2954 0.030 Uiso 1 1 calc R . . C3 C 0.34308(19) 0.3082(3) 0.24081(9) 0.0299(5) Uani 1 1 d . . . H3 H 0.2774 0.2635 0.2124 0.036 Uiso 1 1 calc R . . C4 C 0.4043(2) 0.4653(3) 0.23330(9) 0.0294(5) Uani 1 1 d . . . H4 H 0.3820 0.5275 0.1990 0.035 Uiso 1 1 calc R . . C5 C 0.49632(19) 0.5292(3) 0.27535(8) 0.0259(5) Uani 1 1 d . . . H5 H 0.5368 0.6371 0.2704 0.031 Uiso 1 1 calc R . . C6 C 0.53173(17) 0.4361(2) 0.32609(8) 0.0202(4) Uani 1 1 d . . . C7 C 0.61943(18) 0.5041(3) 0.37215(8) 0.0222(4) Uani 1 1 d . . . H7 H 0.6765 0.5945 0.3661 0.027 Uiso 1 1 calc R . . C8 C 0.62352(17) 0.4414(2) 0.42564(8) 0.0214(4) Uani 1 1 d . . . C9 C 0.6835(2) 0.5447(3) 0.47595(9) 0.0272(5) Uani 1 1 d . . . H9A H 0.6189 0.5694 0.4991 0.041 Uiso 1 1 calc R . . H9B H 0.7168 0.6546 0.4638 0.041 Uiso 1 1 calc R . . H9C H 0.7540 0.4777 0.4979 0.041 Uiso 1 1 calc R . . C10 C 0.41395(17) 0.0332(2) 0.39903(7) 0.0184(4) Uani 1 1 d . . . C11 C 0.41852(18) -0.1482(2) 0.39409(8) 0.0222(4) Uani 1 1 d . . . H11 H 0.4911 -0.2000 0.3828 0.027 Uiso 1 1 calc R . . C12 C 0.32043(19) -0.2548(3) 0.40518(8) 0.0258(5) Uani 1 1 d . . . H12 H 0.3266 -0.3776 0.4013 0.031 Uiso 1 1 calc R . . C13 C 0.21355(19) -0.1830(3) 0.42182(8) 0.0255(5) Uani 1 1 d . . . H13 H 0.1462 -0.2557 0.4294 0.031 Uiso 1 1 calc R . . C14 C 0.20611(18) -0.0037(3) 0.42735(8) 0.0239(4) Uani 1 1 d . . . H14 H 0.1335 0.0470 0.4390 0.029 Uiso 1 1 calc R . . C15 C 0.30432(17) 0.1017(3) 0.41598(8) 0.0210(4) Uani 1 1 d . . . H15 H 0.2972 0.2243 0.4198 0.025 Uiso 1 1 calc R . . C16 C 0.65047(17) 0.0541(2) 0.37092(8) 0.0193(4) Uani 1 1 d . . . C17 C 0.66581(18) 0.0088(3) 0.31679(8) 0.0230(4) Uani 1 1 d . . . H17 H 0.6032 0.0462 0.2859 0.028 Uiso 1 1 calc R . . C18 C 0.76949(19) -0.0891(3) 0.30656(9) 0.0273(5) Uani 1 1 d . . . H18 H 0.7766 -0.1178 0.2692 0.033 Uiso 1 1 calc R . . C19 C 0.86254(19) -0.1447(3) 0.35093(9) 0.0279(5) Uani 1 1 d . . . H19 H 0.9336 -0.2116 0.3442 0.034 Uiso 1 1 calc R . . C20 C 0.85048(18) -0.1015(3) 0.40519(9) 0.0267(5) Uani 1 1 d . . . H20 H 0.9136 -0.1388 0.4359 0.032 Uiso 1 1 calc R . . C21 C 0.74657(18) -0.0039(3) 0.41464(8) 0.0226(4) Uani 1 1 d . . . H21 H 0.7402 0.0248 0.4521 0.027 Uiso 1 1 calc R . . C22 C 0.5660(2) 0.8368(3) 0.13292(9) 0.0331(5) Uani 1 1 d . . . H22A H 0.6493 0.8949 0.1468 0.040 Uiso 1 1 calc R . . H22B H 0.5788 0.7096 0.1381 0.040 Uiso 1 1 calc R . . B1 B 0.5264(2) 0.1596(3) 0.38504(9) 0.0197(5) Uani 1 1 d . . . N1 N 0.47235(14) 0.2794(2) 0.33190(6) 0.0198(4) Uani 1 1 d . . . N2 N 0.56608(15) 0.2910(2) 0.43344(7) 0.0205(4) Uani 1 1 d . . . Cl1 Cl 0.45180(5) 0.90883(7) 0.17246(2) 0.03609(16) Uani 1 1 d . . . Cl2 Cl 0.51653(5) 0.88263(8) 0.06110(2) 0.03630(16) Uani 1 1 d . . . H1 H 0.565(2) 0.260(3) 0.4677(9) 0.028(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0221(10) 0.0284(11) 0.0235(11) -0.0025(9) 0.0038(8) -0.0016(9) C3 0.0236(11) 0.0415(13) 0.0226(11) -0.0018(10) -0.0010(9) 0.0052(10) C4 0.0284(11) 0.0362(13) 0.0246(11) 0.0079(9) 0.0080(9) 0.0103(10) C5 0.0261(11) 0.0264(11) 0.0268(11) 0.0059(9) 0.0095(9) 0.0061(9) C6 0.0174(10) 0.0179(10) 0.0268(11) 0.0001(8) 0.0076(8) 0.0046(8) C7 0.0208(10) 0.0193(10) 0.0276(11) 0.0020(9) 0.0075(8) 0.0000(8) C8 0.0167(10) 0.0193(10) 0.0281(11) -0.0023(8) 0.0041(8) 0.0023(8) C9 0.0283(11) 0.0257(11) 0.0272(11) -0.0050(9) 0.0041(9) -0.0031(9) C10 0.0197(10) 0.0197(10) 0.0145(10) -0.0003(8) -0.0004(7) -0.0003(8) C11 0.0199(10) 0.0221(10) 0.0246(11) -0.0002(8) 0.0043(8) 0.0025(8) C12 0.0295(11) 0.0193(10) 0.0278(11) 0.0034(9) 0.0033(9) -0.0024(9) C13 0.0194(10) 0.0313(12) 0.0248(11) 0.0073(9) 0.0014(8) -0.0051(9) C14 0.0189(10) 0.0307(11) 0.0223(11) 0.0010(9) 0.0044(8) 0.0012(9) C15 0.0218(10) 0.0206(10) 0.0195(10) -0.0014(8) 0.0007(8) 0.0014(8) C16 0.0182(10) 0.0149(9) 0.0251(11) 0.0010(8) 0.0048(8) -0.0049(7) C17 0.0195(10) 0.0242(10) 0.0244(11) 0.0005(9) 0.0019(8) -0.0019(8) C18 0.0259(11) 0.0275(11) 0.0311(12) -0.0036(9) 0.0123(9) -0.0040(9) C19 0.0178(10) 0.0220(10) 0.0466(14) 0.0005(10) 0.0126(9) 0.0016(8) C20 0.0172(10) 0.0253(11) 0.0368(13) 0.0087(9) 0.0024(9) -0.0007(8) C21 0.0220(10) 0.0220(10) 0.0237(11) 0.0018(8) 0.0038(8) -0.0023(8) C22 0.0301(12) 0.0388(13) 0.0298(12) 0.0056(10) 0.0037(9) 0.0079(10) B1 0.0211(11) 0.0176(11) 0.0195(11) 0.0000(9) 0.0010(9) 0.0016(9) N1 0.0186(8) 0.0212(8) 0.0196(9) -0.0016(7) 0.0038(7) 0.0019(7) N2 0.0222(9) 0.0191(8) 0.0199(9) 0.0010(7) 0.0029(7) -0.0012(7) Cl1 0.0403(3) 0.0362(3) 0.0331(3) -0.0008(2) 0.0102(2) 0.0047(2) Cl2 0.0381(3) 0.0413(3) 0.0293(3) 0.0088(2) 0.0057(2) 0.0012(3) _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 C2 N1 1.349(2) . ? C2 C3 1.370(3) . ? C2 H2 0.9500 . ? C3 C4 1.396(3) . ? C3 H3 0.9500 . ? C4 C5 1.367(3) . ? C4 H4 0.9500 . ? C5 C6 1.413(3) . ? C5 H5 0.9500 . ? C6 N1 1.376(2) . ? C6 C7 1.415(3) . ? C7 C8 1.378(3) . ? C7 H7 0.9500 . ? C8 N2 1.335(2) . ? C8 C9 1.496(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.399(3) . ? C10 C15 1.404(3) . ? C10 B1 1.620(3) . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C12 C13 1.385(3) . ? C12 H12 0.9500 . ? C13 C14 1.386(3) . ? C13 H13 0.9500 . ? C14 C15 1.385(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.397(3) . ? C16 C21 1.401(3) . ? C16 B1 1.633(3) . ? C17 C18 1.390(3) . ? C17 H17 0.9500 . ? C18 C19 1.387(3) . ? C18 H18 0.9500 . ? C19 C20 1.386(3) . ? C19 H19 0.9500 . ? C20 C21 1.385(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 Cl2 1.761(2) . ? C22 Cl1 1.766(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? B1 N2 1.547(3) . ? B1 N1 1.601(3) . ? N2 H1 0.87(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C3 122.9(2) . . ? N1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C2 C3 C4 118.32(19) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 119.81(19) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.5(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? N1 C6 C5 118.53(17) . . ? N1 C6 C7 119.15(17) . . ? C5 C6 C7 122.18(18) . . ? C8 C7 C6 121.20(18) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? N2 C8 C7 119.96(18) . . ? N2 C8 C9 118.60(18) . . ? C7 C8 C9 121.31(18) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 116.19(17) . . ? C11 C10 B1 122.66(17) . . ? C15 C10 B1 121.14(17) . . ? C12 C11 C10 122.10(18) . . ? C12 C11 H11 119.0 . . ? C10 C11 H11 119.0 . . ? C13 C12 C11 120.23(18) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 119.19(19) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C15 C14 C13 120.14(18) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C10 122.15(18) . . ? C14 C15 H15 118.9 . . ? C10 C15 H15 118.9 . . ? C17 C16 C21 116.05(17) . . ? C17 C16 B1 123.90(17) . . ? C21 C16 B1 119.98(17) . . ? C18 C17 C16 122.32(18) . . ? C18 C17 H17 118.8 . . ? C16 C17 H17 118.8 . . ? C19 C18 C17 119.99(19) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 119.17(19) . . ? C20 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? C21 C20 C19 120.09(19) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C16 122.38(19) . . ? C20 C21 H21 118.8 . . ? C16 C21 H21 118.8 . . ? Cl2 C22 Cl1 111.47(11) . . ? Cl2 C22 H22A 109.3 . . ? Cl1 C22 H22A 109.3 . . ? Cl2 C22 H22B 109.3 . . ? Cl1 C22 H22B 109.3 . . ? H22A C22 H22B 108.0 . . ? N2 B1 N1 104.16(15) . . ? N2 B1 C10 109.82(16) . . ? N1 B1 C10 110.18(15) . . ? N2 B1 C16 111.42(16) . . ? N1 B1 C16 107.34(16) . . ? C10 B1 C16 113.48(16) . . ? C2 N1 C6 119.92(17) . . ? C2 N1 B1 120.86(16) . . ? C6 N1 B1 118.79(15) . . ? C8 N2 B1 121.58(17) . . ? C8 N2 H1 117.2(15) . . ? B1 N2 H1 120.1(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.23 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.362 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.047 #===END data_22 _database_code_depnum_ccdc_archive 'CCDC 871075' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common diphenylboronpicoline-benzonitrile _chemical_melting_point ? _chemical_formula_moiety 'C25 H21 B N2' _chemical_formula_sum 'C25 H21 B N2' _chemical_formula_weight 360.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.8677(8) _cell_length_b 20.0262(9) _cell_length_c 10.9651(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.7680(10) _cell_angle_gamma 90.00 _cell_volume 3826.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9882 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 25.40 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.69 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9517 _exptl_absorpt_correction_T_max 0.9716 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38225 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.40 _reflns_number_total 7051 _reflns_number_gt 5821 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0408P)^2^+1.4922P] 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 7051 _refine_ls_number_parameters 513 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0917 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 C2 C -0.10135(7) 0.38489(7) 0.52862(12) 0.0213(3) Uani 1 1 d . . . H2 H -0.1175 0.3416 0.4984 0.026 Uiso 1 1 calc R . . C3 C -0.14098(8) 0.43916(7) 0.47186(13) 0.0246(3) Uani 1 1 d . . . H3 H -0.1841 0.4336 0.4043 0.030 Uiso 1 1 calc R . . C4 C -0.11652(8) 0.50306(7) 0.51568(13) 0.0247(3) Uani 1 1 d . . . H4 H -0.1421 0.5417 0.4768 0.030 Uiso 1 1 calc R . . C5 C -0.05539(8) 0.50900(7) 0.61503(13) 0.0233(3) Uani 1 1 d . . . H54 H -0.0388 0.5522 0.6454 0.028 Uiso 1 1 calc R . . C6 C -0.01646(7) 0.45216(6) 0.67337(12) 0.0201(3) Uani 1 1 d . . . C7 C 0.04358(8) 0.45717(6) 0.78200(12) 0.0215(3) Uani 1 1 d . . . H7 H 0.0676 0.4992 0.8033 0.026 Uiso 1 1 calc R . . C8 C 0.06802(7) 0.40292(6) 0.85742(12) 0.0190(3) Uani 1 1 d . . . C9 C 0.12033(7) 0.41011(6) 0.98245(12) 0.0201(3) Uani 1 1 d . . . C10 C 0.12106(8) 0.46816(7) 1.05342(13) 0.0249(3) Uani 1 1 d . . . H10 H 0.0860 0.5032 1.0229 0.030 Uiso 1 1 calc R . . C11 C 0.17227(9) 0.47531(7) 1.16784(13) 0.0289(3) Uani 1 1 d . . . H11 H 0.1725 0.5153 1.2146 0.035 Uiso 1 1 calc R . . C12 C 0.22312(8) 0.42425(8) 1.21426(13) 0.0289(3) Uani 1 1 d . . . H12 H 0.2585 0.4293 1.2923 0.035 Uiso 1 1 calc R . . C13 C 0.22192(8) 0.36597(7) 1.14614(13) 0.0261(3) Uani 1 1 d . . . H13 H 0.2562 0.3307 1.1782 0.031 Uiso 1 1 calc R . . C14 C 0.17109(7) 0.35875(7) 1.03146(12) 0.0219(3) Uani 1 1 d . . . H14 H 0.1708 0.3184 0.9857 0.026 Uiso 1 1 calc R . . C15 C 0.08133(7) 0.32482(6) 0.60052(12) 0.0177(3) Uani 1 1 d . . . C16 C 0.06616(7) 0.32123(6) 0.46918(12) 0.0191(3) Uani 1 1 d . . . H16 H 0.0144 0.3197 0.4237 0.023 Uiso 1 1 calc R . . C17 C 0.12470(8) 0.31983(6) 0.40374(12) 0.0207(3) Uani 1 1 d . . . H17 H 0.1125 0.3173 0.3150 0.025 Uiso 1 1 calc R . . C18 C 0.20064(8) 0.32214(7) 0.46806(13) 0.0235(3) Uani 1 1 d . . . H18 H 0.2408 0.3216 0.4239 0.028 Uiso 1 1 calc R . . C19 C 0.21742(8) 0.32523(7) 0.59744(13) 0.0256(3) Uani 1 1 d . . . H19 H 0.2694 0.3266 0.6423 0.031 Uiso 1 1 calc R . . C20 C 0.15864(8) 0.32630(7) 0.66195(12) 0.0220(3) Uani 1 1 d . . . H20 H 0.1715 0.3281 0.7507 0.026 Uiso 1 1 calc R . . C21 C -0.03758(7) 0.25901(6) 0.66564(11) 0.0171(3) Uani 1 1 d . . . C22 C -0.01679(7) 0.20107(6) 0.61095(12) 0.0206(3) Uani 1 1 d . . . H22 H 0.0256 0.2025 0.5718 0.025 Uiso 1 1 calc R . . C23 C -0.05606(8) 0.14132(7) 0.61178(13) 0.0250(3) Uani 1 1 d . . . H23 H -0.0400 0.1026 0.5746 0.030 Uiso 1 1 calc R . . C24 C -0.11869(8) 0.13824(6) 0.66681(13) 0.0233(3) Uani 1 1 d . . . H24 H -0.1458 0.0975 0.6674 0.028 Uiso 1 1 calc R . . C25 C -0.14146(7) 0.19505(7) 0.72106(12) 0.0217(3) Uani 1 1 d . . . H25 H -0.1847 0.1935 0.7582 0.026 Uiso 1 1 calc R . . C26 C -0.10102(7) 0.25422(6) 0.72109(12) 0.0198(3) Uani 1 1 d . . . H26 H -0.1167 0.2926 0.7598 0.024 Uiso 1 1 calc R . . B1 B 0.01279(8) 0.32659(7) 0.67713(13) 0.0180(3) Uani 1 1 d . . . N1 N -0.04006(6) 0.39038(5) 0.62608(10) 0.0180(2) Uani 1 1 d . . . N2 N 0.04419(6) 0.34165(5) 0.81630(10) 0.0186(2) Uani 1 1 d . . . C27 C 0.32662(8) 0.59030(7) 0.89389(13) 0.0247(3) Uani 1 1 d . . . H27 H 0.3010 0.6321 0.8902 0.030 Uiso 1 1 calc R . . C28 C 0.29719(8) 0.53690(7) 0.94553(14) 0.0298(3) Uani 1 1 d . . . H28 H 0.2522 0.5415 0.9776 0.036 Uiso 1 1 calc R . . C29 C 0.33465(8) 0.47540(7) 0.95003(14) 0.0297(3) Uani 1 1 d . . . H29 H 0.3156 0.4376 0.9860 0.036 Uiso 1 1 calc R . . C30 C 0.39884(8) 0.47013(7) 0.90232(13) 0.0266(3) Uani 1 1 d . . . H30 H 0.4242 0.4283 0.9048 0.032 Uiso 1 1 calc R . . C31 C 0.42795(8) 0.52598(7) 0.84940(12) 0.0217(3) Uani 1 1 d . . . C32 C 0.49152(8) 0.52041(7) 0.79166(13) 0.0240(3) Uani 1 1 d . . . H32 H 0.5244 0.4828 0.8100 0.029 Uiso 1 1 calc R . . C33 C 0.50664(7) 0.56799(6) 0.71012(12) 0.0209(3) Uani 1 1 d . . . C34 C 0.55851(7) 0.55512(7) 0.62339(12) 0.0226(3) Uani 1 1 d . . . C35 C 0.59856(9) 0.49529(8) 0.62614(14) 0.0310(3) Uani 1 1 d . . . H35 H 0.5937 0.4621 0.6859 0.037 Uiso 1 1 calc R . . C36 C 0.64540(9) 0.48327(8) 0.54317(14) 0.0343(4) Uani 1 1 d . . . H36 H 0.6726 0.4423 0.5475 0.041 Uiso 1 1 calc R . . C37 C 0.65295(8) 0.52995(8) 0.45457(14) 0.0309(3) Uani 1 1 d . . . H37 H 0.6849 0.5214 0.3976 0.037 Uiso 1 1 calc R . . C38 C 0.61326(9) 0.58938(8) 0.45007(15) 0.0356(4) Uani 1 1 d . . . H38 H 0.6174 0.6218 0.3887 0.043 Uiso 1 1 calc R . . C39 C 0.56760(8) 0.60214(8) 0.53405(15) 0.0327(3) Uani 1 1 d . . . H39 H 0.5419 0.6438 0.5308 0.039 Uiso 1 1 calc R . . C40 C 0.36734(7) 0.70759(6) 0.74729(12) 0.0195(3) Uani 1 1 d . . . C41 C 0.35822(8) 0.76885(7) 0.80347(13) 0.0235(3) Uani 1 1 d . . . H41 H 0.3891 0.7785 0.8838 0.028 Uiso 1 1 calc R . . C42 C 0.30509(8) 0.81621(7) 0.74478(14) 0.0284(3) Uani 1 1 d . . . H42 H 0.3003 0.8574 0.7854 0.034 Uiso 1 1 calc R . . C43 C 0.25944(8) 0.80368(7) 0.62809(14) 0.0278(3) Uani 1 1 d . . . H43 H 0.2233 0.8360 0.5883 0.033 Uiso 1 1 calc R . . C44 C 0.26693(8) 0.74348(7) 0.56961(13) 0.0269(3) Uani 1 1 d . . . H44 H 0.2360 0.7344 0.4891 0.032 Uiso 1 1 calc R . . C45 C 0.31969(7) 0.69650(7) 0.62896(13) 0.0229(3) Uani 1 1 d . . . H45 H 0.3237 0.6553 0.5879 0.028 Uiso 1 1 calc R . . C46 C 0.49368(7) 0.67614(6) 0.93094(12) 0.0195(3) Uani 1 1 d . . . C47 C 0.57066(7) 0.68675(6) 0.92817(13) 0.0210(3) Uani 1 1 d . . . H47 H 0.5867 0.6788 0.8524 0.025 Uiso 1 1 calc R . . C48 C 0.62443(8) 0.70849(7) 1.03200(13) 0.0246(3) Uani 1 1 d . . . H48 H 0.6762 0.7153 1.0265 0.030 Uiso 1 1 calc R . . C49 C 0.60258(8) 0.72032(7) 1.14379(13) 0.0255(3) Uani 1 1 d . . . H49 H 0.6390 0.7358 1.2148 0.031 Uiso 1 1 calc R . . C50 C 0.52702(8) 0.70934(7) 1.15106(13) 0.0244(3) Uani 1 1 d . . . H50 H 0.5118 0.7165 1.2277 0.029 Uiso 1 1 calc R . . C51 C 0.47366(8) 0.68790(6) 1.04606(12) 0.0215(3) Uani 1 1 d . . . H51 H 0.4220 0.6810 1.0523 0.026 Uiso 1 1 calc R . . B2 B 0.43107(8) 0.65175(7) 0.80700(14) 0.0197(3) Uani 1 1 d . . . N3 N 0.39081(6) 0.58597(5) 0.84782(10) 0.0199(2) Uani 1 1 d . . . N4 N 0.46988(6) 0.62689(6) 0.70415(11) 0.0213(2) Uani 1 1 d . . . H52 H 0.0520(9) 0.3084(8) 0.8709(15) 0.031(4) Uiso 1 1 d . . . H53 H 0.4781(10) 0.6556(9) 0.6462(17) 0.047(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0233(7) 0.0198(7) 0.0208(7) -0.0005(5) 0.0046(5) -0.0006(5) C3 0.0242(7) 0.0250(7) 0.0237(7) 0.0018(6) 0.0032(6) 0.0035(6) C4 0.0286(7) 0.0200(7) 0.0269(7) 0.0056(6) 0.0090(6) 0.0065(6) C5 0.0292(7) 0.0154(6) 0.0264(7) 0.0003(5) 0.0088(6) 0.0012(5) C6 0.0240(7) 0.0159(6) 0.0227(7) -0.0001(5) 0.0099(6) -0.0001(5) C7 0.0260(7) 0.0142(6) 0.0245(7) -0.0016(5) 0.0056(6) -0.0025(5) C8 0.0203(6) 0.0172(6) 0.0213(7) -0.0008(5) 0.0084(5) -0.0015(5) C9 0.0226(7) 0.0180(6) 0.0215(7) 0.0004(5) 0.0088(5) -0.0055(5) C10 0.0310(8) 0.0202(7) 0.0246(7) -0.0001(6) 0.0085(6) -0.0031(6) C11 0.0395(8) 0.0258(7) 0.0227(7) -0.0052(6) 0.0099(6) -0.0108(6) C12 0.0325(8) 0.0344(8) 0.0185(7) 0.0007(6) 0.0029(6) -0.0121(6) C13 0.0249(7) 0.0310(8) 0.0224(7) 0.0046(6) 0.0052(6) -0.0017(6) C14 0.0240(7) 0.0208(7) 0.0219(7) -0.0007(5) 0.0074(6) -0.0026(5) C15 0.0219(6) 0.0098(6) 0.0212(6) 0.0013(5) 0.0048(5) -0.0004(5) C16 0.0202(6) 0.0141(6) 0.0220(7) 0.0001(5) 0.0026(5) -0.0014(5) C17 0.0278(7) 0.0150(6) 0.0203(7) 0.0015(5) 0.0074(6) 0.0001(5) C18 0.0234(7) 0.0199(7) 0.0299(7) 0.0056(6) 0.0118(6) 0.0030(5) C19 0.0189(7) 0.0269(7) 0.0300(8) 0.0084(6) 0.0031(6) 0.0019(6) C20 0.0241(7) 0.0205(7) 0.0207(7) 0.0044(5) 0.0032(5) 0.0005(5) C21 0.0188(6) 0.0167(6) 0.0143(6) 0.0020(5) 0.0008(5) 0.0012(5) C22 0.0229(7) 0.0190(7) 0.0213(7) 0.0009(5) 0.0081(5) 0.0002(5) C23 0.0300(7) 0.0160(7) 0.0296(8) -0.0032(6) 0.0077(6) 0.0002(5) C24 0.0241(7) 0.0163(6) 0.0278(7) 0.0027(5) 0.0021(6) -0.0041(5) C25 0.0178(6) 0.0246(7) 0.0226(7) 0.0046(5) 0.0041(5) 0.0002(5) C26 0.0208(6) 0.0177(6) 0.0204(6) -0.0005(5) 0.0037(5) 0.0024(5) B1 0.0204(7) 0.0147(7) 0.0188(7) 0.0003(6) 0.0037(6) 0.0009(6) N1 0.0210(5) 0.0154(5) 0.0184(5) 0.0011(4) 0.0063(4) 0.0003(4) N2 0.0241(6) 0.0130(5) 0.0186(6) 0.0016(4) 0.0048(5) -0.0005(4) C27 0.0222(7) 0.0241(7) 0.0279(7) 0.0025(6) 0.0057(6) 0.0029(5) C28 0.0249(7) 0.0314(8) 0.0353(8) 0.0073(6) 0.0114(6) 0.0014(6) C29 0.0306(8) 0.0253(8) 0.0336(8) 0.0078(6) 0.0080(6) -0.0037(6) C30 0.0283(7) 0.0200(7) 0.0304(8) 0.0037(6) 0.0045(6) 0.0011(6) C31 0.0218(7) 0.0205(7) 0.0206(7) -0.0003(5) 0.0002(5) 0.0000(5) C32 0.0219(7) 0.0199(7) 0.0295(7) 0.0011(6) 0.0043(6) 0.0033(5) C33 0.0179(6) 0.0205(7) 0.0224(7) -0.0045(5) 0.0001(5) -0.0015(5) C34 0.0185(6) 0.0242(7) 0.0236(7) -0.0069(6) 0.0011(5) -0.0031(5) C35 0.0381(8) 0.0279(8) 0.0278(8) -0.0034(6) 0.0094(7) 0.0043(6) C36 0.0397(9) 0.0310(8) 0.0328(8) -0.0089(7) 0.0095(7) 0.0077(7) C37 0.0238(7) 0.0436(9) 0.0257(8) -0.0108(7) 0.0064(6) -0.0025(6) C38 0.0310(8) 0.0394(9) 0.0399(9) 0.0052(7) 0.0151(7) -0.0014(7) C39 0.0297(8) 0.0280(8) 0.0445(9) 0.0024(7) 0.0168(7) 0.0032(6) C40 0.0191(6) 0.0205(7) 0.0201(7) 0.0037(5) 0.0068(5) -0.0025(5) C41 0.0258(7) 0.0233(7) 0.0215(7) 0.0006(5) 0.0052(6) 0.0013(6) C42 0.0302(8) 0.0227(7) 0.0337(8) 0.0019(6) 0.0103(6) 0.0039(6) C43 0.0220(7) 0.0306(8) 0.0317(8) 0.0136(6) 0.0079(6) 0.0047(6) C44 0.0212(7) 0.0361(8) 0.0224(7) 0.0067(6) 0.0023(6) -0.0028(6) C45 0.0221(7) 0.0245(7) 0.0226(7) -0.0004(6) 0.0057(6) -0.0028(5) C46 0.0224(7) 0.0133(6) 0.0227(7) 0.0019(5) 0.0046(5) 0.0023(5) C47 0.0238(7) 0.0171(6) 0.0226(7) 0.0022(5) 0.0062(6) 0.0004(5) C48 0.0202(7) 0.0194(7) 0.0332(8) 0.0013(6) 0.0036(6) -0.0007(5) C49 0.0256(7) 0.0196(7) 0.0267(7) -0.0029(6) -0.0039(6) 0.0025(5) C50 0.0289(7) 0.0221(7) 0.0216(7) -0.0011(6) 0.0045(6) 0.0060(6) C51 0.0208(7) 0.0200(7) 0.0238(7) 0.0009(5) 0.0050(5) 0.0026(5) B2 0.0210(7) 0.0181(7) 0.0210(7) 0.0005(6) 0.0064(6) -0.0007(6) N3 0.0200(5) 0.0193(6) 0.0193(6) 0.0002(4) 0.0022(4) -0.0003(4) N4 0.0246(6) 0.0194(6) 0.0201(6) 0.0009(5) 0.0054(5) 0.0005(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 C2 N1 1.3550(17) . ? C2 C3 1.3694(19) . ? C2 H2 0.9500 . ? C3 C4 1.402(2) . ? C3 H3 0.9500 . ? C4 C5 1.367(2) . ? C4 H4 0.9500 . ? C5 C6 1.4114(18) . ? C5 H54 0.9500 . ? C6 N1 1.3715(16) . ? C6 C7 1.4195(18) . ? C7 C8 1.3766(18) . ? C7 H7 0.9500 . ? C8 N2 1.3436(16) . ? C8 C9 1.4858(18) . ? C9 C10 1.3975(19) . ? C9 C14 1.3978(19) . ? C10 C11 1.387(2) . ? C10 H10 0.9500 . ? C11 C12 1.388(2) . ? C11 H11 0.9500 . ? C12 C13 1.383(2) . ? C12 H12 0.9500 . ? C13 C14 1.3865(19) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C20 1.3968(18) . ? C15 C16 1.4072(18) . ? C15 B1 1.6314(19) . ? C16 C17 1.3933(18) . ? C16 H16 0.9500 . ? C17 C18 1.3848(19) . ? C17 H17 0.9500 . ? C18 C19 1.385(2) . ? C18 H18 0.9500 . ? C19 C20 1.3901(19) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.3938(18) . ? C21 C26 1.4029(18) . ? C21 B1 1.6147(18) . ? C22 C23 1.3882(18) . ? C22 H22 0.9500 . ? C23 C24 1.3852(19) . ? C23 H23 0.9500 . ? C24 C25 1.3859(19) . ? C24 H24 0.9500 . ? C25 C26 1.3879(18) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? B1 N2 1.5349(18) . ? B1 N1 1.6134(17) . ? N2 H52 0.885(17) . ? C27 N3 1.3543(17) . ? C27 C28 1.368(2) . ? C27 H27 0.9500 . ? C28 C29 1.397(2) . ? C28 H28 0.9500 . ? C29 C30 1.366(2) . ? C29 H29 0.9500 . ? C30 C31 1.4112(19) . ? C30 H30 0.9500 . ? C31 N3 1.3707(17) . ? C31 C32 1.4216(19) . ? C32 C33 1.3737(19) . ? C32 H32 0.9500 . ? C33 N4 1.3445(17) . ? C33 C34 1.4897(19) . ? C34 C35 1.392(2) . ? C34 C39 1.394(2) . ? C35 C36 1.386(2) . ? C35 H35 0.9500 . ? C36 C37 1.376(2) . ? C36 H36 0.9500 . ? C37 C38 1.381(2) . ? C37 H37 0.9500 . ? C38 C39 1.382(2) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? C40 C41 1.3985(19) . ? C40 C45 1.4034(19) . ? C40 B2 1.6266(19) . ? C41 C42 1.3946(19) . ? C41 H41 0.9500 . ? C42 C43 1.380(2) . ? C42 H42 0.9500 . ? C43 C44 1.386(2) . ? C43 H43 0.9500 . ? C44 C45 1.3880(19) . ? C44 H44 0.9500 . ? C45 H45 0.9500 . ? C46 C47 1.3988(18) . ? C46 C51 1.4057(18) . ? C46 B2 1.6324(19) . ? C47 C48 1.3875(19) . ? C47 H47 0.9500 . ? C48 C49 1.387(2) . ? C48 H48 0.9500 . ? C49 C50 1.387(2) . ? C49 H49 0.9500 . ? C50 C51 1.3906(19) . ? C50 H50 0.9500 . ? C51 H51 0.9500 . ? B2 N4 1.5319(18) . ? B2 N3 1.6111(18) . ? N4 H53 0.892(19) . ? 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 N1 C2 C3 122.74(12) . . ? N1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C2 C3 C4 118.54(13) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 119.09(12) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 121.20(12) . . ? C4 C5 H54 119.4 . . ? C6 C5 H54 119.4 . . ? N1 C6 C5 118.47(12) . . ? N1 C6 C7 119.55(11) . . ? C5 C6 C7 121.92(12) . . ? C8 C7 C6 121.93(12) . . ? C8 C7 H7 119.0 . . ? C6 C7 H7 119.0 . . ? N2 C8 C7 118.96(12) . . ? N2 C8 C9 119.09(11) . . ? C7 C8 C9 121.95(11) . . ? C10 C9 C14 118.21(12) . . ? C10 C9 C8 121.40(12) . . ? C14 C9 C8 120.39(12) . . ? C11 C10 C9 120.84(13) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 120.21(13) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 119.53(13) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.44(13) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C9 120.75(13) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? C20 C15 C16 116.16(12) . . ? C20 C15 B1 121.74(11) . . ? C16 C15 B1 122.10(11) . . ? C17 C16 C15 122.09(12) . . ? C17 C16 H16 119.0 . . ? C15 C16 H16 119.0 . . ? C18 C17 C16 119.98(12) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 119.28(12) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C18 C19 C20 120.33(12) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C19 C20 C15 122.15(12) . . ? C19 C20 H20 118.9 . . ? C15 C20 H20 118.9 . . ? C22 C21 C26 116.57(11) . . ? C22 C21 B1 122.30(11) . . ? C26 C21 B1 120.88(11) . . ? C23 C22 C21 122.11(12) . . ? C23 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? C24 C23 C22 119.97(12) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 119.50(12) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 119.92(12) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 121.92(12) . . ? C25 C26 H26 119.0 . . ? C21 C26 H26 119.0 . . ? N2 B1 N1 104.28(10) . . ? N2 B1 C21 108.49(10) . . ? N1 B1 C21 111.29(10) . . ? N2 B1 C15 111.41(10) . . ? N1 B1 C15 106.68(10) . . ? C21 B1 C15 114.24(10) . . ? C2 N1 C6 119.91(11) . . ? C2 N1 B1 121.23(10) . . ? C6 N1 B1 118.40(10) . . ? C8 N2 B1 122.15(11) . . ? C8 N2 H52 117.9(10) . . ? B1 N2 H52 119.6(10) . . ? N3 C27 C28 122.61(13) . . ? N3 C27 H27 118.7 . . ? C28 C27 H27 118.7 . . ? C27 C28 C29 118.59(13) . . ? C27 C28 H28 120.7 . . ? C29 C28 H28 120.7 . . ? C30 C29 C28 119.39(13) . . ? C30 C29 H29 120.3 . . ? C28 C29 H29 120.3 . . ? C29 C30 C31 120.89(13) . . ? C29 C30 H30 119.6 . . ? C31 C30 H30 119.6 . . ? N3 C31 C30 118.57(12) . . ? N3 C31 C32 119.69(12) . . ? C30 C31 C32 121.63(12) . . ? C33 C32 C31 121.80(12) . . ? C33 C32 H32 119.1 . . ? C31 C32 H32 119.1 . . ? N4 C33 C32 118.42(12) . . ? N4 C33 C34 119.13(12) . . ? C32 C33 C34 122.35(12) . . ? C35 C34 C39 117.21(13) . . ? C35 C34 C33 121.63(13) . . ? C39 C34 C33 121.15(12) . . ? C36 C35 C34 121.13(14) . . ? C36 C35 H35 119.4 . . ? C34 C35 H35 119.4 . . ? C37 C36 C35 120.86(14) . . ? C37 C36 H36 119.6 . . ? C35 C36 H36 119.6 . . ? C36 C37 C38 118.75(14) . . ? C36 C37 H37 120.6 . . ? C38 C37 H37 120.6 . . ? C37 C38 C39 120.64(15) . . ? C37 C38 H38 119.7 . . ? C39 C38 H38 119.7 . . ? C38 C39 C34 121.39(14) . . ? C38 C39 H39 119.3 . . ? C34 C39 H39 119.3 . . ? C41 C40 C45 116.11(12) . . ? C41 C40 B2 124.41(12) . . ? C45 C40 B2 119.41(12) . . ? C42 C41 C40 121.80(13) . . ? C42 C41 H41 119.1 . . ? C40 C41 H41 119.1 . . ? C43 C42 C41 120.46(13) . . ? C43 C42 H42 119.8 . . ? C41 C42 H42 119.8 . . ? C42 C43 C44 119.31(13) . . ? C42 C43 H43 120.3 . . ? C44 C43 H43 120.3 . . ? C43 C44 C45 119.85(13) . . ? C43 C44 H44 120.1 . . ? C45 C44 H44 120.1 . . ? C44 C45 C40 122.46(13) . . ? C44 C45 H45 118.8 . . ? C40 C45 H45 118.8 . . ? C47 C46 C51 116.14(12) . . ? C47 C46 B2 121.57(11) . . ? C51 C46 B2 122.29(11) . . ? C48 C47 C46 122.39(13) . . ? C48 C47 H47 118.8 . . ? C46 C47 H47 118.8 . . ? C49 C48 C47 119.99(13) . . ? C49 C48 H48 120.0 . . ? C47 C48 H48 120.0 . . ? C48 C49 C50 119.43(13) . . ? C48 C49 H49 120.3 . . ? C50 C49 H49 120.3 . . ? C49 C50 C51 119.94(13) . . ? C49 C50 H50 120.0 . . ? C51 C50 H50 120.0 . . ? C50 C51 C46 122.09(12) . . ? C50 C51 H51 119.0 . . ? C46 C51 H51 119.0 . . ? N4 B2 N3 103.96(10) . . ? N4 B2 C40 108.52(11) . . ? N3 B2 C40 110.99(10) . . ? N4 B2 C46 111.82(11) . . ? N3 B2 C46 106.21(10) . . ? C40 B2 C46 114.80(11) . . ? C27 N3 C31 119.93(11) . . ? C27 N3 B2 121.21(11) . . ? C31 N3 B2 118.40(10) . . ? C33 N4 B2 123.03(12) . . ? C33 N4 H53 116.3(12) . . ? B2 N4 H53 119.2(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.291 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.036 #===END data_23 _database_code_depnum_ccdc_archive 'CCDC 871076' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common diphenylboronpicoline-4chlorobenzaldehyde _chemical_melting_point ? _chemical_formula_moiety 'C25 H21 B Cl N O' _chemical_formula_sum 'C25 H21 B Cl N O' _chemical_formula_weight 397.69 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' Cl Cl 0.1484 0.1585 '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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4273(8) _cell_length_b 10.2028(9) _cell_length_c 12.7409(12) _cell_angle_alpha 95.7690(10) _cell_angle_beta 105.9230(10) _cell_angle_gamma 104.9040(10) _cell_volume 1000.62(16) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5368 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 25.33 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.207 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9143 _exptl_absorpt_correction_T_max 0.9776 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10160 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3664 _reflns_number_gt 2993 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0406P)^2^+0.7382P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3664 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1085 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 C2 C 0.5209(3) 0.7597(2) 0.45059(18) 0.0270(5) Uani 1 1 d . . . H2 H 0.5122 0.8324 0.4994 0.032 Uiso 1 1 calc R . . C3 C 0.6784(3) 0.7351(2) 0.4675(2) 0.0352(6) Uani 1 1 d . . . H3 H 0.7763 0.7894 0.5273 0.042 Uiso 1 1 calc R . . C4 C 0.6916(3) 0.6303(2) 0.3961(2) 0.0377(6) Uani 1 1 d . . . H4 H 0.8000 0.6145 0.4032 0.045 Uiso 1 1 calc R . . C5 C 0.5453(3) 0.5495(2) 0.3148(2) 0.0372(6) Uani 1 1 d . . . H5 H 0.5510 0.4738 0.2676 0.045 Uiso 1 1 calc R . . C6 C 0.3886(3) 0.5775(2) 0.30094(18) 0.0259(5) Uani 1 1 d . . . C7 C 0.2270(3) 0.4822(2) 0.21713(18) 0.0301(5) Uani 1 1 d . . . H7A H 0.1884 0.3982 0.2474 0.036 Uiso 1 1 calc R . . H7B H 0.2544 0.4536 0.1493 0.036 Uiso 1 1 calc R . . C8 C 0.0798(3) 0.5443(2) 0.18550(16) 0.0238(4) Uani 1 1 d . . . H8 H 0.1095 0.6167 0.1409 0.029 Uiso 1 1 calc R . . C9 C -0.0906(2) 0.4380(2) 0.11740(15) 0.0202(4) Uani 1 1 d . . . C10 C -0.1016(3) 0.3104(2) 0.06066(16) 0.0226(4) Uani 1 1 d . . . H10 H 0.0016 0.2866 0.0653 0.027 Uiso 1 1 calc R . . C11 C -0.2590(3) 0.2170(2) -0.00248(16) 0.0222(4) Uani 1 1 d . . . H11 H -0.2639 0.1306 -0.0411 0.027 Uiso 1 1 calc R . . C12 C -0.4078(3) 0.2520(2) -0.00792(16) 0.0243(4) Uani 1 1 d . . . C13 C -0.4019(3) 0.3773(2) 0.04797(18) 0.0298(5) Uani 1 1 d . . . H13 H -0.5056 0.3999 0.0440 0.036 Uiso 1 1 calc R . . C14 C -0.2435(3) 0.4696(2) 0.10986(17) 0.0262(5) Uani 1 1 d . . . H14 H -0.2394 0.5560 0.1478 0.031 Uiso 1 1 calc R . . C15 C 0.1755(2) 0.76744(19) 0.46536(15) 0.0185(4) Uani 1 1 d . . . C16 C 0.1578(3) 0.6655(2) 0.53083(16) 0.0251(5) Uani 1 1 d . . . H16 H 0.1622 0.5766 0.5039 0.030 Uiso 1 1 calc R . . C17 C 0.1343(3) 0.6901(2) 0.63335(17) 0.0279(5) Uani 1 1 d . . . H17 H 0.1219 0.6184 0.6754 0.033 Uiso 1 1 calc R . . C18 C 0.1289(2) 0.8191(2) 0.67500(16) 0.0237(4) Uani 1 1 d . . . H18 H 0.1142 0.8367 0.7458 0.028 Uiso 1 1 calc R . . C19 C 0.1452(2) 0.9221(2) 0.61238(16) 0.0230(4) Uani 1 1 d . . . H19 H 0.1412 1.0108 0.6400 0.028 Uiso 1 1 calc R . . C20 C 0.1675(2) 0.8955(2) 0.50876(16) 0.0200(4) Uani 1 1 d . . . H20 H 0.1777 0.9670 0.4664 0.024 Uiso 1 1 calc R . . C21 C 0.2190(2) 0.85890(19) 0.27909(15) 0.0174(4) Uani 1 1 d . . . C22 C 0.0690(2) 0.8795(2) 0.21120(16) 0.0203(4) Uani 1 1 d . . . H22 H -0.0396 0.8147 0.2019 0.024 Uiso 1 1 calc R . . C23 C 0.0733(3) 0.9913(2) 0.15696(16) 0.0229(4) Uani 1 1 d . . . H23 H -0.0311 1.0014 0.1111 0.027 Uiso 1 1 calc R . . C24 C 0.2302(3) 1.0882(2) 0.16988(16) 0.0234(4) Uani 1 1 d . . . H24 H 0.2338 1.1653 0.1335 0.028 Uiso 1 1 calc R . . C25 C 0.3809(3) 1.0713(2) 0.23623(17) 0.0240(4) Uani 1 1 d . . . H25 H 0.4890 1.1370 0.2458 0.029 Uiso 1 1 calc R . . C26 C 0.3740(2) 0.9579(2) 0.28905(16) 0.0216(4) Uani 1 1 d . . . H26 H 0.4791 0.9475 0.3337 0.026 Uiso 1 1 calc R . . B1 B 0.1985(3) 0.7301(2) 0.34543(18) 0.0177(5) Uani 1 1 d . . . N1 N 0.37866(19) 0.68459(16) 0.36738(13) 0.0195(4) Uani 1 1 d . . . Cl1 Cl -0.60713(7) 0.13704(6) -0.08747(5) 0.03794(18) Uani 1 1 d . . . O1 O 0.05787(16) 0.60714(12) 0.28276(10) 0.0169(3) 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 C2 0.0218(10) 0.0195(10) 0.0331(12) 0.0043(9) -0.0004(9) 0.0049(8) C3 0.0190(11) 0.0230(11) 0.0514(15) 0.0093(10) -0.0056(10) 0.0024(9) C4 0.0184(11) 0.0239(12) 0.0695(17) 0.0118(11) 0.0076(11) 0.0093(9) C5 0.0213(11) 0.0268(12) 0.0607(16) -0.0015(11) 0.0107(11) 0.0084(10) C6 0.0182(10) 0.0222(11) 0.0355(12) 0.0002(9) 0.0081(9) 0.0055(8) C7 0.0214(11) 0.0286(12) 0.0364(12) -0.0067(9) 0.0080(9) 0.0064(9) C8 0.0216(10) 0.0237(11) 0.0242(10) -0.0017(8) 0.0073(8) 0.0059(9) C9 0.0205(10) 0.0215(10) 0.0176(10) 0.0019(8) 0.0065(8) 0.0045(8) C10 0.0212(10) 0.0245(11) 0.0222(10) 0.0012(8) 0.0074(8) 0.0075(9) C11 0.0252(11) 0.0202(10) 0.0184(10) -0.0009(8) 0.0068(8) 0.0033(8) C12 0.0203(10) 0.0247(11) 0.0208(10) -0.0010(8) 0.0027(8) 0.0005(8) C13 0.0193(10) 0.0297(12) 0.0357(12) -0.0021(9) 0.0033(9) 0.0082(9) C14 0.0247(11) 0.0211(10) 0.0294(11) -0.0029(9) 0.0054(9) 0.0072(9) C15 0.0130(9) 0.0176(10) 0.0189(9) 0.0007(8) -0.0003(7) 0.0011(8) C16 0.0323(11) 0.0169(10) 0.0225(10) 0.0010(8) 0.0038(9) 0.0073(9) C17 0.0345(12) 0.0235(11) 0.0218(11) 0.0064(8) 0.0046(9) 0.0058(9) C18 0.0197(10) 0.0300(11) 0.0175(10) 0.0015(8) 0.0033(8) 0.0044(9) C19 0.0194(10) 0.0209(10) 0.0248(10) -0.0033(8) 0.0042(8) 0.0050(8) C20 0.0173(9) 0.0176(10) 0.0229(10) 0.0035(8) 0.0047(8) 0.0035(8) C21 0.0177(9) 0.0163(9) 0.0173(9) -0.0017(7) 0.0057(7) 0.0051(8) C22 0.0170(10) 0.0191(10) 0.0251(10) 0.0038(8) 0.0077(8) 0.0048(8) C23 0.0210(10) 0.0244(11) 0.0258(10) 0.0046(8) 0.0077(8) 0.0109(9) C24 0.0315(11) 0.0172(10) 0.0262(11) 0.0054(8) 0.0126(9) 0.0107(9) C25 0.0218(10) 0.0175(10) 0.0287(11) -0.0002(8) 0.0082(9) 0.0005(8) C26 0.0189(10) 0.0209(10) 0.0213(10) 0.0012(8) 0.0024(8) 0.0051(8) B1 0.0137(10) 0.0161(11) 0.0219(11) 0.0019(9) 0.0033(9) 0.0049(9) N1 0.0148(8) 0.0152(8) 0.0257(9) 0.0045(7) 0.0024(7) 0.0036(7) Cl1 0.0209(3) 0.0352(3) 0.0422(3) -0.0118(2) 0.0019(2) -0.0023(2) O1 0.0157(7) 0.0149(7) 0.0182(7) -0.0012(5) 0.0046(5) 0.0037(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 C2 N1 1.347(2) . ? C2 C3 1.377(3) . ? C2 H2 0.9500 . ? C3 C4 1.380(3) . ? C3 H3 0.9500 . ? C4 C5 1.370(3) . ? C4 H4 0.9500 . ? C5 C6 1.390(3) . ? C5 H5 0.9500 . ? C6 N1 1.348(3) . ? C6 C7 1.501(3) . ? C7 C8 1.511(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O1 1.417(2) . ? C8 C9 1.522(3) . ? C8 H8 1.0000 . ? C9 C14 1.387(3) . ? C9 C10 1.393(3) . ? C10 C11 1.388(3) . ? C10 H10 0.9500 . ? C11 C12 1.375(3) . ? C11 H11 0.9500 . ? C12 C13 1.381(3) . ? C12 Cl1 1.743(2) . ? C13 C14 1.384(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C20 1.392(3) . ? C15 C16 1.401(3) . ? C15 B1 1.613(3) . ? C16 C17 1.382(3) . ? C16 H16 0.9500 . ? C17 C18 1.386(3) . ? C17 H17 0.9500 . ? C18 C19 1.383(3) . ? C18 H18 0.9500 . ? C19 C20 1.394(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C26 1.396(3) . ? C21 C22 1.402(3) . ? C21 B1 1.630(3) . ? C22 C23 1.389(3) . ? C22 H22 0.9500 . ? C23 C24 1.389(3) . ? C23 H23 0.9500 . ? C24 C25 1.382(3) . ? C24 H24 0.9500 . ? C25 C26 1.392(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? B1 O1 1.460(2) . ? B1 N1 1.660(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 N1 C2 C3 122.5(2) . . ? N1 C2 H2 118.8 . . ? C3 C2 H2 118.8 . . ? C2 C3 C4 118.8(2) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 118.7(2) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 C6 120.5(2) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? N1 C6 C5 120.37(19) . . ? N1 C6 C7 119.57(17) . . ? C5 C6 C7 119.92(19) . . ? C6 C7 C8 114.22(17) . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? O1 C8 C7 109.63(16) . . ? O1 C8 C9 108.50(15) . . ? C7 C8 C9 112.76(16) . . ? O1 C8 H8 108.6 . . ? C7 C8 H8 108.6 . . ? C9 C8 H8 108.6 . . ? C14 C9 C10 117.81(18) . . ? C14 C9 C8 118.83(17) . . ? C10 C9 C8 123.36(17) . . ? C11 C10 C9 121.88(18) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C12 C11 C10 118.58(18) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C13 121.10(18) . . ? C11 C12 Cl1 119.52(16) . . ? C13 C12 Cl1 119.37(16) . . ? C12 C13 C14 119.47(19) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C13 C14 C9 121.15(19) . . ? C13 C14 H14 119.4 . . ? C9 C14 H14 119.4 . . ? C20 C15 C16 116.50(18) . . ? C20 C15 B1 124.22(17) . . ? C16 C15 B1 119.26(17) . . ? C17 C16 C15 122.09(19) . . ? C17 C16 H16 119.0 . . ? C15 C16 H16 119.0 . . ? C16 C17 C18 120.12(19) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C19 C18 C17 119.33(18) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C20 119.92(18) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C15 C20 C19 122.03(18) . . ? C15 C20 H20 119.0 . . ? C19 C20 H20 119.0 . . ? C26 C21 C22 115.82(17) . . ? C26 C21 B1 125.66(17) . . ? C22 C21 B1 118.38(16) . . ? C23 C22 C21 122.41(18) . . ? C23 C22 H22 118.8 . . ? C21 C22 H22 118.8 . . ? C24 C23 C22 119.96(18) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C25 C24 C23 119.28(18) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C24 C25 C26 119.89(19) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C25 C26 C21 122.64(18) . . ? C25 C26 H26 118.7 . . ? C21 C26 H26 118.7 . . ? O1 B1 C15 108.24(15) . . ? O1 B1 C21 113.82(15) . . ? C15 B1 C21 113.86(15) . . ? O1 B1 N1 106.04(14) . . ? C15 B1 N1 106.87(15) . . ? C21 B1 N1 107.50(15) . . ? C2 N1 C6 118.93(17) . . ? C2 N1 B1 119.43(16) . . ? C6 N1 B1 121.59(15) . . ? C8 O1 B1 114.85(14) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.630 _refine_diff_density_min -0.516 _refine_diff_density_rms 0.047 #===END data_24 _database_code_depnum_ccdc_archive 'CCDC 871077' #TrackingRef '- cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common diphenylboronpicoline-n,n-dimethylacetamide _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 B N O' _chemical_formula_sum 'C20 H18 B N O' _chemical_formula_weight 299.16 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4944(4) _cell_length_b 9.8689(5) _cell_length_c 10.9392(6) _cell_angle_alpha 63.4990(10) _cell_angle_beta 87.6370(10) _cell_angle_gamma 81.6400(10) _cell_volume 811.67(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5379 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 25.38 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9598 _exptl_absorpt_correction_T_max 0.9746 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8217 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.37 _reflns_number_total 2966 _reflns_number_gt 2558 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.1678P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2966 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0901 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 C2 C 0.57001(14) 0.72493(13) 0.54797(12) 0.0242(3) Uani 1 1 d . . . H2 H 0.5174 0.7321 0.4699 0.029 Uiso 1 1 calc R . . C3 C 0.72915(15) 0.73830(14) 0.54172(13) 0.0286(3) Uani 1 1 d . . . H3 H 0.7858 0.7553 0.4606 0.034 Uiso 1 1 calc R . . C4 C 0.80557(14) 0.72643(14) 0.65672(14) 0.0296(3) Uani 1 1 d . . . H4 H 0.9166 0.7308 0.6566 0.035 Uiso 1 1 calc R . . C5 C 0.71936(14) 0.70837(14) 0.77045(13) 0.0269(3) Uani 1 1 d . . . H5 H 0.7706 0.7027 0.8485 0.032 Uiso 1 1 calc R . . C6 C 0.55626(13) 0.69819(12) 0.77244(11) 0.0211(3) Uani 1 1 d . . . C7 C 0.45782(14) 0.69004(13) 0.88458(11) 0.0223(3) Uani 1 1 d . . . H7 H 0.5065 0.6702 0.9687 0.027 Uiso 1 1 calc R . . C8 C 0.29781(13) 0.70996(12) 0.87321(11) 0.0206(2) Uani 1 1 d . . . C9 C 0.18981(15) 0.72755(15) 0.97771(12) 0.0278(3) Uani 1 1 d . . . H9A H 0.1271 0.8297 0.9377 0.042 Uiso 1 1 calc R . . H9B H 0.2533 0.7146 1.0560 0.042 Uiso 1 1 calc R . . H9C H 0.1180 0.6499 1.0081 0.042 Uiso 1 1 calc R . . C10 C 0.21848(13) 0.72154(13) 0.53328(11) 0.0197(2) Uani 1 1 d . . . C11 C 0.16980(15) 0.87925(14) 0.45965(12) 0.0264(3) Uani 1 1 d . . . H11 H 0.1932 0.9454 0.4962 0.032 Uiso 1 1 calc R . . C12 C 0.08856(15) 0.94133(14) 0.33509(12) 0.0291(3) Uani 1 1 d . . . H12 H 0.0561 1.0486 0.2879 0.035 Uiso 1 1 calc R . . C13 C 0.05443(14) 0.84738(14) 0.27904(12) 0.0256(3) Uani 1 1 d . . . H13 H 0.0002 0.8900 0.1929 0.031 Uiso 1 1 calc R . . C14 C 0.10001(14) 0.69091(14) 0.34958(12) 0.0245(3) Uani 1 1 d . . . H14 H 0.0764 0.6254 0.3124 0.029 Uiso 1 1 calc R . . C15 C 0.18037(13) 0.62996(13) 0.47487(12) 0.0219(3) Uani 1 1 d . . . H15 H 0.2104 0.5224 0.5224 0.026 Uiso 1 1 calc R . . C16 C 0.33368(13) 0.46705(13) 0.75995(11) 0.0195(2) Uani 1 1 d . . . C17 C 0.21606(13) 0.39107(13) 0.84607(11) 0.0224(3) Uani 1 1 d . . . H17 H 0.1257 0.4496 0.8619 0.027 Uiso 1 1 calc R . . C18 C 0.22742(14) 0.23258(14) 0.90916(12) 0.0258(3) Uani 1 1 d . . . H18 H 0.1460 0.1845 0.9678 0.031 Uiso 1 1 calc R . . C19 C 0.35709(14) 0.14439(13) 0.88678(12) 0.0257(3) Uani 1 1 d . . . H19 H 0.3640 0.0361 0.9285 0.031 Uiso 1 1 calc R . . C20 C 0.47629(14) 0.21559(13) 0.80313(12) 0.0256(3) Uani 1 1 d . . . H20 H 0.5662 0.1562 0.7878 0.031 Uiso 1 1 calc R . . C21 C 0.46422(14) 0.37433(13) 0.74152(11) 0.0223(3) Uani 1 1 d . . . H21 H 0.5475 0.4214 0.6849 0.027 Uiso 1 1 calc R . . B1 B 0.31027(15) 0.65241(15) 0.67951(13) 0.0198(3) Uani 1 1 d . . . N1 N 0.48584(11) 0.70190(10) 0.66114(9) 0.0196(2) Uani 1 1 d . . . O1 O 0.22140(9) 0.72179(9) 0.76353(8) 0.02041(19) 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 C2 0.0300(6) 0.0215(6) 0.0234(6) -0.0121(5) 0.0058(5) -0.0052(5) C3 0.0303(7) 0.0226(6) 0.0362(7) -0.0156(6) 0.0135(5) -0.0089(5) C4 0.0213(6) 0.0247(6) 0.0468(8) -0.0192(6) 0.0061(5) -0.0062(5) C5 0.0231(6) 0.0264(6) 0.0339(7) -0.0156(5) -0.0015(5) -0.0039(5) C6 0.0222(6) 0.0168(5) 0.0240(6) -0.0089(5) -0.0021(5) -0.0021(4) C7 0.0257(6) 0.0225(6) 0.0191(6) -0.0097(5) -0.0021(5) -0.0023(5) C8 0.0267(6) 0.0168(5) 0.0183(5) -0.0080(5) -0.0005(5) -0.0020(5) C9 0.0294(6) 0.0312(7) 0.0241(6) -0.0143(5) 0.0017(5) -0.0015(5) C10 0.0180(5) 0.0213(6) 0.0205(6) -0.0100(5) 0.0029(4) -0.0030(4) C11 0.0342(7) 0.0215(6) 0.0254(6) -0.0119(5) -0.0054(5) -0.0033(5) C12 0.0370(7) 0.0200(6) 0.0272(6) -0.0077(5) -0.0070(5) -0.0023(5) C13 0.0256(6) 0.0291(7) 0.0201(6) -0.0090(5) -0.0040(5) -0.0032(5) C14 0.0250(6) 0.0279(6) 0.0263(6) -0.0170(5) -0.0005(5) -0.0039(5) C15 0.0224(6) 0.0198(6) 0.0237(6) -0.0106(5) -0.0002(5) -0.0006(5) C16 0.0202(5) 0.0235(6) 0.0165(5) -0.0103(5) -0.0038(4) -0.0025(5) C17 0.0192(6) 0.0244(6) 0.0241(6) -0.0114(5) -0.0022(5) -0.0011(5) C18 0.0236(6) 0.0266(6) 0.0258(6) -0.0087(5) -0.0016(5) -0.0085(5) C19 0.0310(6) 0.0193(6) 0.0254(6) -0.0080(5) -0.0085(5) -0.0033(5) C20 0.0279(6) 0.0241(6) 0.0242(6) -0.0118(5) -0.0044(5) 0.0030(5) C21 0.0232(6) 0.0241(6) 0.0191(6) -0.0093(5) 0.0009(4) -0.0031(5) B1 0.0188(6) 0.0214(7) 0.0210(6) -0.0113(5) 0.0014(5) -0.0024(5) N1 0.0211(5) 0.0173(5) 0.0209(5) -0.0092(4) 0.0013(4) -0.0022(4) O1 0.0203(4) 0.0225(4) 0.0199(4) -0.0113(3) -0.0006(3) -0.0006(3) _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 C2 N1 1.3485(14) . ? C2 C3 1.3733(17) . ? C2 H2 0.9500 . ? C3 C4 1.3897(18) . ? C3 H3 0.9500 . ? C4 C5 1.3714(18) . ? C4 H4 0.9500 . ? C5 C6 1.4022(16) . ? C5 H5 0.9500 . ? C6 N1 1.3621(14) . ? C6 C7 1.4344(16) . ? C7 C8 1.3475(16) . ? C7 H7 0.9500 . ? C8 O1 1.3386(13) . ? C8 C9 1.4910(16) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C15 1.3955(16) . ? C10 C11 1.4014(16) . ? C10 B1 1.6144(16) . ? C11 C12 1.3849(17) . ? C11 H11 0.9500 . ? C12 C13 1.3855(17) . ? C12 H12 0.9500 . ? C13 C14 1.3847(17) . ? C13 H13 0.9500 . ? C14 C15 1.3886(16) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.3992(16) . ? C16 C21 1.3995(16) . ? C16 B1 1.6225(16) . ? C17 C18 1.3893(16) . ? C17 H17 0.9500 . ? C18 C19 1.3855(17) . ? C18 H18 0.9500 . ? C19 C20 1.3832(17) . ? C19 H19 0.9500 . ? C20 C21 1.3913(16) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? B1 O1 1.4958(14) . ? B1 N1 1.6133(15) . ? 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 N1 C2 C3 122.27(11) . . ? N1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C2 C3 C4 118.53(11) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 119.43(11) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 120.53(12) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? N1 C6 C5 118.93(11) . . ? N1 C6 C7 118.04(10) . . ? C5 C6 C7 122.99(11) . . ? C8 C7 C6 121.43(10) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? O1 C8 C7 122.59(10) . . ? O1 C8 C9 113.83(10) . . ? C7 C8 C9 123.52(10) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 116.56(10) . . ? C15 C10 B1 122.81(10) . . ? C11 C10 B1 120.62(10) . . ? C12 C11 C10 121.81(11) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C13 120.18(11) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 119.46(11) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 119.80(11) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C10 122.18(11) . . ? C14 C15 H15 118.9 . . ? C10 C15 H15 118.9 . . ? C17 C16 C21 116.23(10) . . ? C17 C16 B1 120.56(10) . . ? C21 C16 B1 123.08(10) . . ? C18 C17 C16 122.00(11) . . ? C18 C17 H17 119.0 . . ? C16 C17 H17 119.0 . . ? C19 C18 C17 120.23(11) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 119.34(11) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? C19 C20 C21 119.88(11) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C20 C21 C16 122.31(11) . . ? C20 C21 H21 118.8 . . ? C16 C21 H21 118.8 . . ? O1 B1 N1 106.36(9) . . ? O1 B1 C10 108.24(9) . . ? N1 B1 C10 110.62(9) . . ? O1 B1 C16 111.12(9) . . ? N1 B1 C16 106.60(9) . . ? C10 B1 C16 113.66(9) . . ? C2 N1 C6 120.16(10) . . ? C2 N1 B1 122.03(9) . . ? C6 N1 B1 117.14(9) . . ? C8 O1 B1 117.23(8) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.234 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.036 #===END