data_ap3149a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H14 B N, C H B11 Cl11' _chemical_formula_sum 'C10 H14 B12 Cl11 N' _chemical_formula_weight 667.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 Orthorhombic _symmetry_space_group_name_H-M Pbam loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z' 'x-1/2, -y-1/2, z' '-x-1/2, y-1/2, z' _cell_length_a 14.1671(3) _cell_length_b 20.0121(5) _cell_length_c 9.5338(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2702.96(11) _cell_formula_units_Z 4 _cell_measurement_temperature 85(2) _cell_measurement_reflns_used 9701 _cell_measurement_theta_min 1.84 _cell_measurement_theta_max 35.39 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.641 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 1.137 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7800 _exptl_absorpt_correction_T_max 0.8130 _exptl_absorpt_process_details ; Blessing, R. Acta Cryst. (1995) A51 33-38. Sheldrick, G. SADABS (Version 2008/1) Bruker AXS area detector absorption and other corrections, University of Gottingen, Germany 2008. ; _exptl_special_details ; 5190 frames x 10 sec. @ 5.055 cm; 0.5 deg. steps in omega. 0.45 deg. in phi ; _diffrn_ambient_temperature 85(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 151618 _diffrn_reflns_av_R_equivalents 0.0574 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 36.38 _reflns_number_total 6882 _reflns_number_gt 5395 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART-APEX' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Both the borolidine cation and carba-closo-dodecaborate anion lie on mirror planes of the crystal lattice. The dodecaborate is crystallographically ordered with the mirror plane containing the C-H substituted vertex of the icosohedral anion. The mirror plane of the borolidine cation is perpindicular to the plane of the aromatic ring and contains the nitrogen aton (N1) and the attached methyl groups (C1-C2). As the cation does not possess mirror symmetry it is crystallographically disordered. The two orientations are related by a 180 degree rotation parallel to the molecular plane. SAME restraints were used so that the geometry of both orientations were held to be similar. 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^)+(0.0478P)^2^+1.3578P] 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 6882 _refine_ls_number_parameters 219 _refine_ls_number_restraints 86 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1005 _refine_ls_wR_factor_gt 0.0923 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.002 _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 N1 N 0.16144(8) 0.39188(6) 0.5111(2) 0.0168(3) Uani 0.50 1 d PU A -1 C1 C 0.10040(11) 0.33091(7) 0.5006(8) 0.0266(3) Uani 0.50 1 d S A -1 H1A H 0.0528 0.3318 0.5751 0.040 Uiso 0.50 1 calc PR A -1 H1B H 0.1396 0.2908 0.5107 0.040 Uiso 0.50 1 calc PR A -1 H1C H 0.0690 0.3302 0.4090 0.040 Uiso 0.50 1 calc PR A -1 C2 C 0.10209(10) 0.45388(7) 0.4936(6) 0.0255(3) Uani 0.50 1 d P A -1 H2A H 0.0778 0.4559 0.3974 0.038 Uiso 0.50 1 calc PR A -1 H2B H 0.1408 0.4935 0.5123 0.038 Uiso 0.50 1 calc PR A -1 H2C H 0.0491 0.4526 0.5596 0.038 Uiso 0.50 1 calc PR A -1 B1 B 0.23587(18) 0.39280(12) 0.3881(2) 0.0260(5) Uani 0.50 1 d PU A -1 H1 H 0.2236 0.3891 0.2905 0.031 Uiso 0.50 1 calc PR A -1 C3 C 0.33002(13) 0.40079(9) 0.45748(19) 0.0222(3) Uani 0.50 1 d PU A -1 C4 C 0.42211(15) 0.40569(11) 0.4014(3) 0.0359(5) Uani 0.50 1 d PDU A -1 H4 H 0.4322 0.4038 0.3030 0.043 Uiso 0.50 1 calc PR A -1 C5 C 0.49657(12) 0.41327(9) 0.4918(6) 0.0395(5) Uani 0.50 1 d PDU A -1 H5 H 0.5591 0.4148 0.4560 0.047 Uiso 0.50 1 calc PR A -1 C6 C 0.48096(14) 0.41875(11) 0.6372(3) 0.0372(5) Uani 0.50 1 d PDU A -1 H6 H 0.5333 0.4255 0.6978 0.045 Uiso 0.50 1 calc PR A -1 C7 C 0.39062(13) 0.41456(9) 0.6944(2) 0.0260(4) Uani 0.50 1 d PDU A -1 H7 H 0.3803 0.4186 0.7925 0.031 Uiso 0.50 1 calc PR A -1 C8 C 0.31648(12) 0.40417(8) 0.6020(2) 0.0190(3) Uani 0.50 1 d PDU A -1 C9 C 0.21552(13) 0.39452(11) 0.6442(2) 0.0208(4) Uani 0.50 1 d PU A -1 H9A H 0.2079 0.3524 0.6976 0.025 Uiso 0.50 1 calc PR A -1 H9B H 0.1937 0.4322 0.7033 0.025 Uiso 0.50 1 calc PR A -1 C10 C 0.38017(8) 0.19661(5) 0.0000 0.0176(2) Uani 1 2 d S . . H10 H 0.4359(12) 0.2229(9) 0.0000 0.025(4) Uiso 1 2 d S . . Cl1 Cl 0.27484(3) 0.328139(14) 0.0000 0.02609(7) Uani 1 2 d S . . Cl2 Cl 0.100419(16) 0.222582(11) 0.19096(2) 0.02554(5) Uani 1 1 d . . . Cl3 Cl 0.07932(2) 0.064034(17) 0.0000 0.02772(7) Uani 1 2 d S . . Cl4 Cl 0.31267(2) -0.017309(13) 0.0000 0.02309(6) Uani 1 2 d S . . Cl5 Cl 0.479242(15) 0.094642(11) 0.18365(2) 0.02501(4) Uani 1 1 d . . . Cl6 Cl 0.352794(17) 0.238449(11) 0.30394(2) 0.02538(5) Uani 1 1 d . . . Cl7 Cl 0.233562(17) 0.074046(11) 0.31242(2) 0.02537(5) Uani 1 1 d . . . B2 B 0.27622(10) 0.23996(6) 0.0000 0.0183(2) Uani 1 2 d S . . B3 B 0.19606(6) 0.18809(4) 0.09408(10) 0.01799(17) Uani 1 1 d . . . B4 B 0.18556(9) 0.11069(6) 0.0000 0.0182(2) Uani 1 2 d S . . B5 B 0.29907(9) 0.07060(6) 0.0000 0.0162(2) Uani 1 2 d S . . B6 B 0.37810(6) 0.12333(4) 0.09330(10) 0.01765(17) Uani 1 1 d . . . B7 B 0.31521(7) 0.19549(4) 0.15206(10) 0.01797(17) Uani 1 1 d . . . B8 B 0.26003(6) 0.11555(4) 0.15214(10) 0.01772(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 N1 0.0207(4) 0.0198(4) 0.0100(6) -0.0018(6) 0.0012(6) 0.0018(4) C1 0.0323(6) 0.0190(5) 0.0286(6) -0.009(2) 0.011(2) -0.0033(5) C2 0.0268(6) 0.0195(5) 0.0303(9) 0.0033(17) -0.0036(18) 0.0022(4) B1 0.0360(10) 0.0234(8) 0.0185(8) -0.0035(7) 0.0017(8) 0.0030(8) C3 0.0237(7) 0.0191(6) 0.0239(7) -0.0007(5) 0.0046(6) 0.0008(6) C4 0.0316(8) 0.0304(9) 0.0458(11) -0.0039(9) 0.0172(8) -0.0004(8) C5 0.0231(6) 0.0389(8) 0.0566(13) 0.001(2) 0.0149(16) -0.0008(6) C6 0.0217(8) 0.0311(9) 0.0586(13) 0.0110(10) -0.0047(9) -0.0035(7) C7 0.0223(7) 0.0222(7) 0.0335(9) 0.0061(7) -0.0057(7) -0.0035(6) C8 0.0197(6) 0.0141(6) 0.0231(7) 0.0018(6) 0.0025(6) 0.0015(5) C9 0.0191(7) 0.0262(8) 0.0171(8) 0.0000(6) -0.0025(6) -0.0012(6) C10 0.0178(4) 0.0142(4) 0.0208(5) 0.000 0.000 -0.0017(4) Cl1 0.03832(15) 0.01165(10) 0.02831(14) 0.000 0.000 0.00295(10) Cl2 0.02385(8) 0.02607(9) 0.02672(10) -0.00280(8) 0.00551(8) 0.00766(7) Cl3 0.01935(11) 0.02557(13) 0.03823(17) 0.000 0.000 -0.00662(10) Cl4 0.02823(13) 0.01135(9) 0.02971(14) 0.000 0.000 0.00092(9) Cl5 0.02175(8) 0.02455(9) 0.02873(10) 0.00056(8) -0.00744(7) 0.00446(7) Cl6 0.03116(10) 0.02273(8) 0.02223(9) -0.00679(7) -0.00440(8) 0.00005(8) Cl7 0.02775(9) 0.02643(9) 0.02194(9) 0.00839(7) 0.00448(7) 0.00230(8) B2 0.0232(5) 0.0129(4) 0.0188(5) 0.000 0.000 0.0022(4) B3 0.0185(3) 0.0158(3) 0.0197(4) -0.0009(3) 0.0014(3) 0.0024(3) B4 0.0176(5) 0.0164(5) 0.0206(5) 0.000 0.000 -0.0018(4) B5 0.0176(5) 0.0118(4) 0.0193(5) 0.000 0.000 0.0006(4) B6 0.0185(3) 0.0149(3) 0.0196(4) 0.0002(3) -0.0020(3) 0.0009(3) B7 0.0205(3) 0.0151(3) 0.0183(4) -0.0014(3) -0.0004(3) 0.0008(3) B8 0.0201(3) 0.0152(3) 0.0178(3) 0.0016(3) 0.0019(3) 0.0004(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 N1 C9 1.483(3) . ? N1 C1 1.4988(18) . ? N1 C2 1.5082(18) . ? N1 B1 1.577(3) . ? B1 C3 1.497(3) . ? C3 C8 1.392(3) . ? C3 C4 1.413(3) . ? C4 C5 1.370(4) . ? C5 C6 1.408(6) . ? C6 C7 1.394(3) . ? C7 C8 1.387(3) . ? C8 C9 1.498(3) . ? C10 B2 1.7093(18) . ? C10 B6 1.7155(13) 6 ? C10 B6 1.7156(13) . ? C10 B7 1.7173(11) 6 ? C10 B7 1.7173(11) . ? Cl1 B2 1.7647(13) . ? Cl2 B3 1.7792(9) . ? Cl3 B4 1.7712(13) . ? Cl4 B5 1.7698(12) . ? Cl5 B6 1.7677(9) . ? Cl6 B7 1.7663(10) . ? Cl7 B8 1.7791(10) . ? B2 B3 1.7809(15) 6 ? B2 B3 1.7809(15) . ? B2 B7 1.7885(12) . ? B2 B7 1.7886(12) 6 ? B3 B7 1.7822(13) . ? B3 B3 1.7940(19) 6 ? B3 B4 1.7961(14) . ? B3 B8 1.7987(13) . ? B4 B3 1.7962(14) 6 ? B4 B8 1.7963(12) . ? B4 B8 1.7963(12) 6 ? B4 B5 1.7972(18) . ? B5 B6 1.7771(14) . ? B5 B6 1.7771(14) 6 ? B5 B8 1.7941(12) . ? B5 B8 1.7941(12) 6 ? B6 B8 1.7711(13) . ? B6 B6 1.7790(19) 6 ? B6 B7 1.7869(13) . ? B7 B8 1.7805(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C1 112.6(3) . . ? C9 N1 C2 110.7(2) . . ? C1 N1 C2 109.92(12) . . ? C9 N1 B1 106.87(14) . . ? C1 N1 B1 110.2(3) . . ? C2 N1 B1 106.3(2) . . ? C3 B1 N1 105.59(16) . . ? C8 C3 C4 119.85(19) . . ? C8 C3 B1 108.62(17) . . ? C4 C3 B1 131.53(19) . . ? C5 C4 C3 118.7(3) . . ? C4 C5 C6 120.4(2) . . ? C7 C6 C5 121.7(2) . . ? C8 C7 C6 117.1(2) . . ? C7 C8 C3 122.11(17) . . ? C7 C8 C9 124.85(18) . . ? C3 C8 C9 113.03(17) . . ? N1 C9 C8 105.52(15) . . ? B2 C10 B6 114.78(7) . 6 ? B2 C10 B6 114.78(7) . . ? B6 C10 B6 62.46(7) 6 . ? B2 C10 B7 62.93(5) . 6 ? B6 C10 B7 62.73(5) 6 6 ? B6 C10 B7 114.66(7) . 6 ? B2 C10 B7 62.93(5) . . ? B6 C10 B7 114.66(7) 6 . ? B6 C10 B7 62.74(5) . . ? B7 C10 B7 115.16(9) 6 . ? C10 B2 Cl1 121.13(9) . . ? C10 B2 B3 104.69(7) . 6 ? Cl1 B2 B3 125.15(7) . 6 ? C10 B2 B3 104.69(7) . . ? Cl1 B2 B3 125.15(7) . . ? B3 B2 B3 60.49(8) 6 . ? C10 B2 B7 58.76(5) . . ? Cl1 B2 B7 120.07(5) . . ? B3 B2 B7 108.37(8) 6 . ? B3 B2 B7 59.91(5) . . ? C10 B2 B7 58.76(5) . 6 ? Cl1 B2 B7 120.07(5) . 6 ? B3 B2 B7 59.91(5) 6 6 ? B3 B2 B7 108.37(8) . 6 ? B7 B2 B7 108.30(9) . 6 ? Cl2 B3 B2 121.40(6) . . ? Cl2 B3 B7 121.87(6) . . ? B2 B3 B7 60.26(5) . . ? Cl2 B3 B3 121.27(3) . 6 ? B2 B3 B3 59.76(4) . 6 ? B7 B3 B3 108.07(4) . 6 ? Cl2 B3 B4 122.05(7) . . ? B2 B3 B4 107.70(6) . . ? B7 B3 B4 107.76(7) . . ? B3 B3 B4 60.04(4) 6 . ? Cl2 B3 B8 122.48(6) . . ? B2 B3 B8 107.71(7) . . ? B7 B3 B8 59.63(5) . . ? B3 B3 B8 107.93(4) 6 . ? B4 B3 B8 59.96(5) . . ? Cl3 B4 B3 121.67(7) . . ? Cl3 B4 B3 121.67(7) . 6 ? B3 B4 B3 59.92(7) . 6 ? Cl3 B4 B8 121.85(5) . . ? B3 B4 B8 60.09(5) . . ? B3 B4 B8 107.93(8) 6 . ? Cl3 B4 B8 121.85(5) . 6 ? B3 B4 B8 107.93(8) . 6 ? B3 B4 B8 60.09(5) 6 6 ? B8 B4 B8 107.70(9) . 6 ? Cl3 B4 B5 121.67(8) . . ? B3 B4 B5 108.11(7) . . ? B3 B4 B5 108.11(7) 6 . ? B8 B4 B5 59.90(5) . . ? B8 B4 B5 59.90(5) 6 . ? Cl4 B5 B6 121.44(7) . . ? Cl4 B5 B6 121.44(7) . 6 ? B6 B5 B6 60.07(7) . 6 ? Cl4 B5 B8 122.14(5) . . ? B6 B5 B8 59.46(5) . . ? B6 B5 B8 107.53(7) 6 . ? Cl4 B5 B8 122.14(5) . 6 ? B6 B5 B8 107.53(7) . 6 ? B6 B5 B8 59.46(5) 6 6 ? B8 B5 B8 107.89(9) . 6 ? Cl4 B5 B4 122.76(8) . . ? B6 B5 B4 107.38(7) . . ? B6 B5 B4 107.38(7) 6 . ? B8 B5 B4 60.02(5) . . ? B8 B5 B4 60.02(5) 6 . ? C10 B6 Cl5 121.09(6) . . ? C10 B6 B8 104.81(7) . . ? Cl5 B6 B8 125.64(6) . . ? C10 B6 B5 105.00(6) . . ? Cl5 B6 B5 124.18(6) . . ? B8 B6 B5 60.75(5) . . ? C10 B6 B6 58.77(4) . 6 ? Cl5 B6 B6 119.17(3) . 6 ? B8 B6 B6 108.47(4) . 6 ? B5 B6 B6 59.97(4) . 6 ? C10 B6 B7 58.68(5) . . ? Cl5 B6 B7 120.92(6) . . ? B8 B6 B7 60.05(5) . . ? B5 B6 B7 108.82(7) . . ? B6 B6 B7 108.27(4) 6 . ? C10 B7 Cl6 121.61(6) . . ? C10 B7 B8 104.33(7) . . ? Cl6 B7 B8 124.70(6) . . ? C10 B7 B3 104.29(7) . . ? Cl6 B7 B3 125.47(6) . . ? B8 B7 B3 60.64(5) . . ? C10 B7 B6 58.58(6) . . ? Cl6 B7 B6 120.00(6) . . ? B8 B7 B6 59.53(5) . . ? B3 B7 B6 107.93(6) . . ? C10 B7 B2 58.32(6) . . ? Cl6 B7 B2 121.02(6) . . ? B8 B7 B2 108.18(7) . . ? B3 B7 B2 59.83(6) . . ? B6 B7 B2 107.58(7) . . ? B6 B8 Cl7 120.81(6) . . ? B6 B8 B7 60.41(5) . . ? Cl7 B8 B7 120.82(6) . . ? B6 B8 B5 59.79(6) . . ? Cl7 B8 B5 121.69(6) . . ? B7 B8 B5 108.35(7) . . ? B6 B8 B4 107.68(7) . . ? Cl7 B8 B4 122.99(6) . . ? B7 B8 B4 107.83(7) . . ? B5 B8 B4 60.07(6) . . ? B6 B8 B3 107.90(6) . . ? Cl7 B8 B3 122.34(6) . . ? B7 B8 B3 59.73(5) . . ? B5 B8 B3 108.13(7) . . ? B4 B8 B3 59.95(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 36.38 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.816 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.095 #===END data_jj129a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H30 B N' _chemical_formula_sum 'C18 H30 B N' _chemical_formula_weight 271.24 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 6.0015(2) _cell_length_b 10.1798(2) _cell_length_c 13.9479(3) _cell_angle_alpha 80.0930(6) _cell_angle_beta 88.3963(6) _cell_angle_gamma 85.7197(6) _cell_volume 836.98(5) _cell_formula_units_Z 2 _cell_measurement_temperature 85(2) _cell_measurement_reflns_used 9958 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 31.71 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.076 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.060 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9845 _exptl_absorpt_correction_T_max 0.9928 _exptl_absorpt_process_details ; Blessing, R. Acta Cryst. (1995) A51 33-38. Sheldrick, G. SADABS (Version 2008/1) Bruker AXS area detector absorption and other corrections, University of Gottingen, Germany 2008. ; _exptl_special_details ; 3615 frames x 15 sec @ 5.070 cm; 0.5 deg omega scans, 0.45 deg phi scans ; _diffrn_ambient_temperature 85(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26822 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 31.72 _reflns_number_total 5648 _reflns_number_gt 4635 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX-I' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0731P)^2^+0.1634P] 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 5648 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1339 _refine_ls_wR_factor_gt 0.1235 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 B1 B 0.58332(15) 0.43207(9) 0.22295(7) 0.01522(17) Uani 1 1 d . . . H1 H 0.7010(19) 0.5184(12) 0.1966(9) 0.018 Uiso 1 1 d . . . N1 N 0.32025(11) 0.49624(7) 0.21823(5) 0.01402(14) Uani 1 1 d . . . C1 C 0.24173(14) 0.49350(8) 0.11707(6) 0.01633(16) Uani 1 1 d . . . H1A H 0.2760 0.5761 0.0721 0.020 Uiso 1 1 calc R . . H1B H 0.0788 0.4837 0.1170 0.020 Uiso 1 1 calc R . . C2 C 0.37120(14) 0.37280(8) 0.08857(6) 0.01608(16) Uani 1 1 d . . . C3 C 0.31073(15) 0.30239(9) 0.01755(6) 0.01910(17) Uani 1 1 d . . . H3A H 0.1760 0.3273 -0.0172 0.023 Uiso 1 1 calc R . . C4 C 0.45165(16) 0.19433(9) -0.00169(7) 0.02147(18) Uani 1 1 d . . . H4A H 0.4129 0.1449 -0.0499 0.026 Uiso 1 1 calc R . . C5 C 0.64896(16) 0.15876(9) 0.04959(7) 0.02115(18) Uani 1 1 d . . . H5A H 0.7459 0.0863 0.0352 0.025 Uiso 1 1 calc R . . C6 C 0.70508(15) 0.22908(9) 0.12205(6) 0.01883(17) Uani 1 1 d . . . H6A H 0.8394 0.2036 0.1570 0.023 Uiso 1 1 calc R . . C7 C 0.56544(14) 0.33659(8) 0.14351(6) 0.01571(16) Uani 1 1 d . . . C8 C 0.60018(14) 0.36584(9) 0.33737(6) 0.01772(17) Uani 1 1 d . . . H8A H 0.6993 0.2826 0.3455 0.021 Uiso 1 1 calc R . . H8B H 0.6620 0.4287 0.3747 0.021 Uiso 1 1 calc R . . C9 C 0.35930(14) 0.33487(8) 0.37435(6) 0.01614(16) Uani 1 1 d . . . C10 C 0.20252(13) 0.39496(8) 0.28937(6) 0.01584(16) Uani 1 1 d . . . H10A H 0.1579 0.3229 0.2560 0.019 Uiso 1 1 calc R . . H10B H 0.0657 0.4383 0.3150 0.019 Uiso 1 1 calc R . . C11 C 0.33466(17) 0.18415(9) 0.39793(7) 0.02376(19) Uani 1 1 d . . . H11A H 0.4253 0.1452 0.4545 0.036 Uiso 1 1 calc R . . H11B H 0.3854 0.1429 0.3419 0.036 Uiso 1 1 calc R . . H11C H 0.1775 0.1677 0.4125 0.036 Uiso 1 1 calc R . . C12 C 0.29219(16) 0.39605(9) 0.46500(7) 0.02065(18) Uani 1 1 d . . . H12A H 0.1383 0.3764 0.4843 0.031 Uiso 1 1 calc R . . H12B H 0.3025 0.4931 0.4503 0.031 Uiso 1 1 calc R . . H12C H 0.3929 0.3577 0.5183 0.031 Uiso 1 1 calc R . . C13 C 0.30469(13) 0.63325(8) 0.24438(6) 0.01580(16) Uani 1 1 d . . . H13A H 0.3927 0.6917 0.1958 0.019 Uiso 1 1 calc R . . H13B H 0.3755 0.6278 0.3083 0.019 Uiso 1 1 calc R . . C14 C 0.06936(14) 0.69971(9) 0.24981(7) 0.01875(17) Uani 1 1 d . . . H14A H -0.0197 0.6416 0.2981 0.022 Uiso 1 1 calc R . . H14B H -0.0016 0.7067 0.1857 0.022 Uiso 1 1 calc R . . C15 C 0.06052(14) 0.84033(8) 0.27788(6) 0.01697(16) Uani 1 1 d . . . C16 C -0.18654(15) 0.88691(10) 0.28853(8) 0.02366(19) Uani 1 1 d . . . H16A H -0.1982 0.9768 0.3053 0.035 Uiso 1 1 calc R . . H16B H -0.2570 0.8250 0.3401 0.035 Uiso 1 1 calc R . . H16C H -0.2623 0.8886 0.2269 0.035 Uiso 1 1 calc R . . C17 C 0.17541(15) 0.83606(9) 0.37545(7) 0.02036(18) Uani 1 1 d . . . H17A H 0.3371 0.8189 0.3671 0.031 Uiso 1 1 calc R . . H17B H 0.1179 0.7646 0.4239 0.031 Uiso 1 1 calc R . . H17C H 0.1446 0.9220 0.3976 0.031 Uiso 1 1 calc R . . C18 C 0.17014(16) 0.94014(9) 0.19910(7) 0.02198(18) Uani 1 1 d . . . H18A H 0.0954 0.9437 0.1370 0.033 Uiso 1 1 calc R . . H18B H 0.3285 0.9116 0.1922 0.033 Uiso 1 1 calc R . . H18C H 0.1567 1.0290 0.2177 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0121(4) 0.0166(4) 0.0168(4) -0.0027(3) -0.0003(3) 0.0000(3) N1 0.0133(3) 0.0140(3) 0.0150(3) -0.0027(2) -0.0005(2) -0.0013(2) C1 0.0161(4) 0.0176(4) 0.0150(4) -0.0023(3) -0.0023(3) 0.0002(3) C2 0.0174(4) 0.0165(4) 0.0141(4) -0.0019(3) 0.0003(3) -0.0013(3) C3 0.0215(4) 0.0200(4) 0.0158(4) -0.0022(3) -0.0015(3) -0.0030(3) C4 0.0297(5) 0.0187(4) 0.0169(4) -0.0047(3) 0.0016(3) -0.0049(3) C5 0.0271(4) 0.0161(4) 0.0200(4) -0.0036(3) 0.0036(3) 0.0002(3) C6 0.0203(4) 0.0172(4) 0.0181(4) -0.0019(3) 0.0008(3) 0.0012(3) C7 0.0162(4) 0.0157(4) 0.0147(4) -0.0013(3) 0.0010(3) -0.0012(3) C8 0.0146(4) 0.0215(4) 0.0169(4) -0.0030(3) -0.0020(3) -0.0001(3) C9 0.0167(4) 0.0167(4) 0.0151(4) -0.0025(3) -0.0005(3) -0.0024(3) C10 0.0138(3) 0.0169(4) 0.0165(4) -0.0012(3) 0.0004(3) -0.0029(3) C11 0.0279(5) 0.0168(4) 0.0260(5) -0.0009(3) -0.0031(3) -0.0028(3) C12 0.0227(4) 0.0236(4) 0.0164(4) -0.0046(3) 0.0022(3) -0.0047(3) C13 0.0142(4) 0.0144(3) 0.0191(4) -0.0037(3) -0.0001(3) -0.0007(3) C14 0.0138(4) 0.0188(4) 0.0248(4) -0.0070(3) -0.0014(3) -0.0002(3) C15 0.0139(4) 0.0168(4) 0.0200(4) -0.0034(3) 0.0013(3) 0.0003(3) C16 0.0157(4) 0.0234(4) 0.0314(5) -0.0054(4) 0.0024(3) 0.0026(3) C17 0.0216(4) 0.0193(4) 0.0208(4) -0.0052(3) -0.0001(3) -0.0015(3) C18 0.0211(4) 0.0201(4) 0.0228(4) -0.0002(3) 0.0034(3) 0.0014(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 B1 C7 1.6052(13) . ? B1 C8 1.6249(13) . ? B1 N1 1.6616(11) . ? N1 C13 1.4970(10) . ? N1 C10 1.5048(11) . ? N1 C1 1.5054(11) . ? C1 C2 1.5099(12) . ? C2 C3 1.3892(12) . ? C2 C7 1.4038(12) . ? C3 C4 1.3954(13) . ? C4 C5 1.3926(14) . ? C5 C6 1.3969(13) . ? C6 C7 1.3969(12) . ? C8 C9 1.5575(12) . ? C9 C11 1.5303(12) . ? C9 C12 1.5342(12) . ? C9 C10 1.5464(12) . ? C13 C14 1.5255(12) . ? C14 C15 1.5446(12) . ? C15 C18 1.5322(13) . ? C15 C16 1.5338(12) . ? C15 C17 1.5352(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 B1 C8 119.19(7) . . ? C7 B1 N1 97.49(6) . . ? C8 B1 N1 100.77(6) . . ? C13 N1 C10 113.91(6) . . ? C13 N1 C1 113.53(6) . . ? C10 N1 C1 109.08(6) . . ? C13 N1 B1 110.59(6) . . ? C10 N1 B1 102.57(6) . . ? C1 N1 B1 106.35(6) . . ? N1 C1 C2 103.88(6) . . ? C3 C2 C7 122.30(8) . . ? C3 C2 C1 125.74(8) . . ? C7 C2 C1 111.96(7) . . ? C2 C3 C4 118.73(8) . . ? C5 C4 C3 120.19(8) . . ? C4 C5 C6 120.32(8) . . ? C5 C6 C7 120.58(8) . . ? C6 C7 C2 117.83(8) . . ? C6 C7 B1 131.54(8) . . ? C2 C7 B1 110.63(7) . . ? C9 C8 B1 107.25(7) . . ? C11 C9 C12 108.59(7) . . ? C11 C9 C10 108.33(7) . . ? C12 C9 C10 110.09(7) . . ? C11 C9 C8 111.32(7) . . ? C12 C9 C8 112.39(7) . . ? C10 C9 C8 106.03(7) . . ? N1 C10 C9 109.84(6) . . ? N1 C13 C14 115.90(7) . . ? C13 C14 C15 114.26(7) . . ? C18 C15 C16 108.90(7) . . ? C18 C15 C17 109.52(7) . . ? C16 C15 C17 108.71(7) . . ? C18 C15 C14 111.37(7) . . ? C16 C15 C14 107.37(7) . . ? C17 C15 C14 110.89(7) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 31.72 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.491 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.054 #===END data_jj119 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H20 B N' _chemical_formula_sum 'C14 H20 B N' _chemical_formula_weight 213.12 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 20.341(3) _cell_length_b 6.1762(9) _cell_length_c 19.118(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.547(18) _cell_angle_gamma 90.00 _cell_volume 2400.9(7) _cell_formula_units_Z 8 _cell_measurement_temperature 85(2) _cell_measurement_reflns_used 8505 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 29.57 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9868 _exptl_absorpt_correction_T_max 0.9947 _exptl_absorpt_process_details ; Blessing, R. Acta Cryst. (1995) A51 33-38. Sheldrick, G. SADABS (Version 2008/1) Bruker AXS area detector absorption and other corrections, University of Gottingen, Germany 2008. ; _exptl_special_details ; 2487 frames x 30 sec @ 5.070 cm; 0.5 deg omega scans, 0.45 deg phi scans ; _diffrn_ambient_temperature 85(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 'Bruker SMART APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25403 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 29.60 _reflns_number_total 3374 _reflns_number_gt 2755 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0797P)^2^+1.8204P] 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 3374 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1455 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 B1 B 0.18414(6) 1.0210(2) 0.13711(7) 0.0144(2) Uani 1 1 d . . . H1 H 0.1709(7) 1.108(3) 0.1867(8) 0.016(4) Uiso 1 1 d . . . N1 N 0.17445(5) 0.75910(17) 0.15047(5) 0.0152(2) Uani 1 1 d . . . C1 C 0.23654(6) 0.6840(2) 0.18708(6) 0.0184(3) Uani 1 1 d . . . H1A H 0.2454 0.5299 0.1766 0.022 Uiso 1 1 calc R . . H1B H 0.2338 0.7021 0.2384 0.022 Uiso 1 1 calc R . . C2 C 0.28921(6) 0.8278(2) 0.15816(6) 0.0158(2) Uani 1 1 d . . . C3 C 0.35645(6) 0.7847(2) 0.16059(6) 0.0181(3) Uani 1 1 d . . . H3A H 0.3730 0.6549 0.1811 0.022 Uiso 1 1 calc R . . C4 C 0.39894(6) 0.9362(2) 0.13232(7) 0.0199(3) Uani 1 1 d . . . H4A H 0.4450 0.9106 0.1339 0.024 Uiso 1 1 calc R . . C5 C 0.37420(6) 1.1249(2) 0.10177(7) 0.0207(3) Uani 1 1 d . . . H5A H 0.4035 1.2273 0.0825 0.025 Uiso 1 1 calc R . . C6 C 0.30652(6) 1.1646(2) 0.09935(6) 0.0182(3) Uani 1 1 d . . . H6A H 0.2902 1.2934 0.0780 0.022 Uiso 1 1 calc R . . C7 C 0.26257(6) 1.01689(19) 0.12792(6) 0.0146(2) Uani 1 1 d . . . C8 C 0.13565(6) 1.0587(2) 0.06992(6) 0.0174(2) Uani 1 1 d . . . H8A H 0.1538 1.1781 0.0408 0.021 Uiso 1 1 calc R . . C9 C 0.06459(6) 1.1156(2) 0.08820(7) 0.0215(3) Uani 1 1 d . . . H9A H 0.0620 1.2740 0.0955 0.026 Uiso 1 1 calc R . . H9B H 0.0356 1.0799 0.0474 0.026 Uiso 1 1 calc R . . C10 C 0.03726(6) 1.0029(2) 0.15270(7) 0.0237(3) Uani 1 1 d . . . H10A H 0.0565 1.0737 0.1950 0.028 Uiso 1 1 calc R . . H10B H -0.0108 1.0274 0.1528 0.028 Uiso 1 1 calc R . . C11 C 0.04978(6) 0.7602(2) 0.15855(7) 0.0222(3) Uani 1 1 d . . . H11A H 0.0461 0.6966 0.1111 0.027 Uiso 1 1 calc R . . H11B H 0.0146 0.6955 0.1866 0.027 Uiso 1 1 calc R . . C12 C 0.11615(6) 0.6948(2) 0.19128(7) 0.0205(3) Uani 1 1 d . . . H12A H 0.1203 0.7604 0.2384 0.025 Uiso 1 1 calc R . . H12B H 0.1167 0.5355 0.1972 0.025 Uiso 1 1 calc R . . C13 C 0.17041(6) 0.6675(2) 0.07699(7) 0.0193(3) Uani 1 1 d . . . H13A H 0.1427 0.5358 0.0758 0.023 Uiso 1 1 calc R . . H13B H 0.2149 0.6283 0.0613 0.023 Uiso 1 1 calc R . . C14 C 0.13997(6) 0.8431(2) 0.02845(7) 0.0211(3) Uani 1 1 d . . . H14A H 0.0955 0.7979 0.0120 0.025 Uiso 1 1 calc R . . H14B H 0.1676 0.8633 -0.0129 0.025 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0146(5) 0.0131(6) 0.0156(6) -0.0009(4) -0.0002(4) -0.0004(4) N1 0.0143(4) 0.0160(5) 0.0154(5) 0.0009(4) 0.0000(4) -0.0007(4) C1 0.0165(5) 0.0186(6) 0.0200(6) 0.0050(4) -0.0019(4) 0.0004(4) C2 0.0165(5) 0.0170(6) 0.0139(5) -0.0001(4) -0.0004(4) -0.0009(4) C3 0.0170(5) 0.0199(6) 0.0174(5) 0.0001(4) -0.0014(4) 0.0023(4) C4 0.0151(5) 0.0244(6) 0.0202(6) -0.0025(5) 0.0002(4) 0.0008(4) C5 0.0177(6) 0.0219(6) 0.0227(6) 0.0001(5) 0.0042(4) -0.0030(5) C6 0.0186(6) 0.0165(6) 0.0197(6) 0.0012(4) 0.0017(4) 0.0000(4) C7 0.0157(5) 0.0151(5) 0.0131(5) -0.0014(4) 0.0004(4) -0.0002(4) C8 0.0173(5) 0.0162(6) 0.0187(5) 0.0001(4) -0.0018(4) 0.0000(4) C9 0.0159(5) 0.0207(6) 0.0278(6) -0.0014(5) -0.0031(5) 0.0012(4) C10 0.0161(5) 0.0249(7) 0.0302(7) -0.0040(5) 0.0021(5) 0.0000(5) C11 0.0160(5) 0.0258(7) 0.0251(6) 0.0012(5) 0.0030(5) -0.0046(5) C12 0.0185(6) 0.0220(6) 0.0210(6) 0.0039(5) 0.0032(4) -0.0047(5) C13 0.0196(6) 0.0177(6) 0.0206(6) -0.0060(4) 0.0005(4) -0.0008(4) C14 0.0223(6) 0.0243(6) 0.0167(5) -0.0049(5) -0.0005(4) -0.0012(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 B1 C7 1.6099(17) . ? B1 C8 1.6152(17) . ? B1 N1 1.6502(17) . ? B1 H1 1.130(15) . ? N1 C12 1.4909(15) . ? N1 C1 1.5006(15) . ? N1 C13 1.5146(16) . ? C1 C2 1.5079(17) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.3927(16) . ? C2 C7 1.4055(16) . ? C3 C4 1.3928(18) . ? C3 H3A 0.9500 . ? C4 C5 1.3918(19) . ? C4 H4A 0.9500 . ? C5 C6 1.3978(17) . ? C5 H5A 0.9500 . ? C6 C7 1.3987(17) . ? C6 H6A 0.9500 . ? C8 C9 1.5368(17) . ? C8 C14 1.5533(18) . ? C8 H8A 1.0000 . ? C9 C10 1.5333(19) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.524(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5270(18) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.5458(19) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 B1 C8 120.08(10) . . ? C7 B1 N1 97.14(9) . . ? C8 B1 N1 101.04(9) . . ? C7 B1 H1 111.0(8) . . ? C8 B1 H1 116.4(8) . . ? N1 B1 H1 107.8(8) . . ? C12 N1 C1 110.18(9) . . ? C12 N1 C13 111.21(10) . . ? C1 N1 C13 109.94(9) . . ? C12 N1 B1 116.25(9) . . ? C1 N1 B1 105.82(9) . . ? C13 N1 B1 103.07(9) . . ? N1 C1 C2 104.15(9) . . ? N1 C1 H1A 110.9 . . ? C2 C1 H1A 110.9 . . ? N1 C1 H1B 110.9 . . ? C2 C1 H1B 110.9 . . ? H1A C1 H1B 108.9 . . ? C3 C2 C7 122.67(11) . . ? C3 C2 C1 125.60(11) . . ? C7 C2 C1 111.73(10) . . ? C2 C3 C4 118.56(11) . . ? C2 C3 H3A 120.7 . . ? C4 C3 H3A 120.7 . . ? C5 C4 C3 120.28(11) . . ? C5 C4 H4A 119.9 . . ? C3 C4 H4A 119.9 . . ? C4 C5 C6 120.35(12) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C5 C6 C7 120.81(11) . . ? C5 C6 H6A 119.6 . . ? C7 C6 H6A 119.6 . . ? C6 C7 C2 117.33(11) . . ? C6 C7 B1 132.70(11) . . ? C2 C7 B1 109.91(10) . . ? C9 C8 C14 112.24(10) . . ? C9 C8 B1 114.21(10) . . ? C14 C8 B1 103.91(10) . . ? C9 C8 H8A 108.8 . . ? C14 C8 H8A 108.8 . . ? B1 C8 H8A 108.8 . . ? C10 C9 C8 116.29(11) . . ? 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 116.22(11) . . ? C11 C10 H10A 108.2 . . ? C9 C10 H10A 108.2 . . ? C11 C10 H10B 108.2 . . ? C9 C10 H10B 108.2 . . ? H10A C10 H10B 107.4 . . ? C10 C11 C12 115.75(11) . . ? C10 C11 H11A 108.3 . . ? C12 C11 H11A 108.3 . . ? C10 C11 H11B 108.3 . . ? C12 C11 H11B 108.3 . . ? H11A C11 H11B 107.4 . . ? N1 C12 C11 114.97(10) . . ? N1 C12 H12A 108.5 . . ? C11 C12 H12A 108.5 . . ? N1 C12 H12B 108.5 . . ? C11 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? N1 C13 C14 107.80(10) . . ? N1 C13 H13A 110.1 . . ? C14 C13 H13A 110.1 . . ? N1 C13 H13B 110.1 . . ? C14 C13 H13B 110.1 . . ? H13A C13 H13B 108.5 . . ? C13 C14 C8 108.81(10) . . ? C13 C14 H14A 109.9 . . ? C8 C14 H14A 109.9 . . ? C13 C14 H14B 109.9 . . ? C8 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 B1 N1 C12 154.39(9) . . . . ? C8 B1 N1 C12 -82.98(11) . . . . ? C7 B1 N1 C1 31.74(10) . . . . ? C8 B1 N1 C1 154.37(9) . . . . ? C7 B1 N1 C13 -83.70(10) . . . . ? C8 B1 N1 C13 38.92(11) . . . . ? C12 N1 C1 C2 -158.62(10) . . . . ? C13 N1 C1 C2 78.46(11) . . . . ? B1 N1 C1 C2 -32.20(11) . . . . ? N1 C1 C2 C3 -161.01(11) . . . . ? N1 C1 C2 C7 19.45(13) . . . . ? C7 C2 C3 C4 0.46(18) . . . . ? C1 C2 C3 C4 -179.03(11) . . . . ? C2 C3 C4 C5 -0.66(18) . . . . ? C3 C4 C5 C6 0.21(19) . . . . ? C4 C5 C6 C7 0.48(19) . . . . ? C5 C6 C7 C2 -0.67(18) . . . . ? C5 C6 C7 B1 176.17(12) . . . . ? C3 C2 C7 C6 0.20(17) . . . . ? C1 C2 C7 C6 179.76(10) . . . . ? C3 C2 C7 B1 -177.33(11) . . . . ? C1 C2 C7 B1 2.23(13) . . . . ? C8 B1 C7 C6 55.36(18) . . . . ? N1 B1 C7 C6 162.56(12) . . . . ? C8 B1 C7 C2 -127.62(11) . . . . ? N1 B1 C7 C2 -20.42(11) . . . . ? C7 B1 C8 C9 -165.40(11) . . . . ? N1 B1 C8 C9 89.57(11) . . . . ? C7 B1 C8 C14 71.99(13) . . . . ? N1 B1 C8 C14 -33.04(11) . . . . ? C14 C8 C9 C10 81.73(14) . . . . ? B1 C8 C9 C10 -36.22(15) . . . . ? C8 C9 C10 C11 -45.88(16) . . . . ? C9 C10 C11 C12 84.45(15) . . . . ? C1 N1 C12 C11 -179.26(11) . . . . ? C13 N1 C12 C11 -57.09(14) . . . . ? B1 N1 C12 C11 60.41(14) . . . . ? C10 C11 C12 N1 -64.61(15) . . . . ? C12 N1 C13 C14 95.11(12) . . . . ? C1 N1 C13 C14 -142.58(10) . . . . ? B1 N1 C13 C14 -30.13(12) . . . . ? N1 C13 C14 C8 9.27(13) . . . . ? C9 C8 C14 C13 -107.66(12) . . . . ? B1 C8 C14 C13 16.24(13) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.60 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.565 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.058