# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1804 data_global # 1. SUBMISSION DETAILS COMPOUND lc179 _publ_contact_author ; Toupet Loic G.M.C.M.-UMR6626 Universite de Rennes Campus de Beaulieu 35042 RENNES cedex , FRANCE ; _publ_contact_author_email 'loic.toupet@univ-rennes1.fr' _publ_contact_author_fax '(33) 2 99 28 67 17' _publ_contact_author_phone '(33) 2 99 28 60 65' _publ_requested_journal ' ' _publ_requested_coeditor_name ? _publ_contact_letter ; ; data_lc179 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H12 B Cl N2' _chemical_formula_weight 242.51 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 ? _symmetry_space_group_name_H-M ? 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 8.539(2) _cell_length_b 11.828(3) _cell_length_c 12.989(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.07(2) _cell_angle_gamma 90.00 _cell_volume 1306.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.270 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _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 2452 _diffrn_reflns_av_R_equivalents 0.0815 _diffrn_reflns_av_sigmaI/netI 0.0649 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2291 _reflns_number_gt 1187 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1493P)^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 SHELXL _refine_ls_extinction_coef 0.004(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2291 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1543 _refine_ls_R_factor_gt 0.0665 _refine_ls_wR_factor_ref 0.2206 _refine_ls_wR_factor_gt 0.1758 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.19112(13) 0.45907(11) -0.01395(10) 0.0918(6) Uani 1 1 d . . . N1 N 0.5983(3) 0.2544(2) 0.1174(2) 0.0522(8) Uani 1 1 d . . . N2 N 0.6937(5) -0.0378(3) 0.1340(3) 0.0943(13) Uani 1 1 d . . . C1 C 0.5650(4) 0.3527(3) 0.1604(3) 0.0631(10) Uani 1 1 d . . . H1 H 0.6269 0.3772 0.2186 0.076 Uiso 1 1 calc R . . C2 C 0.4418(4) 0.4189(3) 0.1212(3) 0.0683(11) Uani 1 1 d . . . H2 H 0.4211 0.4880 0.1514 0.082 Uiso 1 1 calc R . . C3 C 0.3506(4) 0.3807(3) 0.0369(3) 0.0595(10) Uani 1 1 d . . . C4 C 0.3825(5) 0.2801(3) -0.0071(3) 0.0712(11) Uani 1 1 d . . . H4 H 0.3206 0.2531 -0.0644 0.085 Uiso 1 1 calc R . . C5 C 0.5089(5) 0.2197(3) 0.0358(3) 0.0689(11) Uani 1 1 d . . . H5 H 0.5326 0.1511 0.0059 0.083 Uiso 1 1 calc R . . C6 C 0.7160(4) 0.0555(3) 0.1471(3) 0.0635(10) Uani 1 1 d . . . C7 C 0.9022(4) 0.2302(4) 0.1134(4) 0.0815(13) Uani 1 1 d . . . H7A H 0.8921 0.2094 0.0409 0.098 Uiso 1 1 calc R . . H7B H 0.9055 0.3121 0.1172 0.098 Uiso 1 1 calc R . . C8 C 1.0536(4) 0.1844(4) 0.1625(3) 0.0648(11) Uani 1 1 d . . . C9 C 1.1271(5) 0.0929(5) 0.1235(4) 0.0843(13) Uani 1 1 d . . . H9 H 1.0806 0.0573 0.0647 0.101 Uiso 1 1 calc R . . C10 C 1.2678(6) 0.0521(5) 0.1689(5) 0.1037(18) Uani 1 1 d . . . H10 H 1.3146 -0.0098 0.1398 0.124 Uiso 1 1 calc R . . C11 C 1.3376(5) 0.0997(6) 0.2536(5) 0.0990(18) Uani 1 1 d . . . H11 H 1.4327 0.0721 0.2839 0.119 Uiso 1 1 calc R . . C12 C 1.2668(6) 0.1891(6) 0.2945(4) 0.1005(17) Uani 1 1 d . . . H12 H 1.3137 0.2230 0.3540 0.121 Uiso 1 1 calc R . . C13 C 1.1256(6) 0.2311(4) 0.2495(4) 0.0850(13) Uani 1 1 d . . . H13 H 1.0793 0.2926 0.2795 0.102 Uiso 1 1 calc R . . B1 B 0.7482(5) 0.1861(4) 0.1660(4) 0.0603(11) Uani 1 1 d . . . H1A H 0.7622 0.2005 0.2405 0.072 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 Cl1 0.0629(7) 0.0938(9) 0.1169(11) 0.0120(7) -0.0026(6) 0.0320(6) N1 0.0501(16) 0.0450(16) 0.0613(18) -0.0011(14) 0.0047(14) 0.0015(13) N2 0.098(3) 0.053(2) 0.127(4) 0.001(2) -0.017(2) 0.013(2) C1 0.055(2) 0.056(2) 0.076(3) -0.0152(19) -0.0061(18) 0.0017(17) C2 0.061(2) 0.056(2) 0.088(3) -0.011(2) 0.005(2) 0.0133(19) C3 0.0463(19) 0.060(2) 0.073(3) 0.010(2) 0.0100(18) 0.0071(17) C4 0.069(2) 0.066(3) 0.074(3) -0.003(2) -0.014(2) 0.009(2) C5 0.081(3) 0.051(2) 0.071(3) -0.0134(19) -0.011(2) 0.017(2) C6 0.059(2) 0.054(3) 0.075(3) 0.005(2) -0.0076(19) 0.0107(18) C7 0.058(2) 0.082(3) 0.104(3) 0.028(2) 0.006(2) 0.001(2) C8 0.050(2) 0.066(2) 0.079(3) 0.017(2) 0.0102(19) -0.0034(19) C9 0.066(3) 0.101(3) 0.086(3) -0.005(3) 0.003(2) 0.008(3) C10 0.069(3) 0.115(5) 0.130(5) 0.007(4) 0.021(3) 0.028(3) C11 0.050(3) 0.139(5) 0.108(4) 0.047(4) 0.006(3) -0.001(3) C12 0.074(3) 0.128(5) 0.098(4) 0.000(3) -0.002(3) -0.033(3) C13 0.072(3) 0.080(3) 0.103(4) -0.010(3) 0.007(3) -0.012(2) B1 0.056(2) 0.058(3) 0.066(3) 0.006(2) -0.003(2) 0.003(2) _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 Cl1 C3 1.730(4) . ? N1 C5 1.315(5) . ? N1 C1 1.332(4) . ? N1 B1 1.595(5) . ? N2 C6 1.130(5) . ? C1 C2 1.372(5) . ? C1 H1 0.9300 . ? C2 C3 1.363(5) . ? C2 H2 0.9300 . ? C3 C4 1.358(5) . ? C4 C5 1.371(5) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 B1 1.584(6) . ? C7 C8 1.492(5) . ? C7 B1 1.621(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C13 1.356(6) . ? C8 C9 1.370(6) . ? C9 C10 1.378(6) . ? C9 H9 0.9300 . ? C10 C11 1.329(8) . ? C10 H10 0.9300 . ? C11 C12 1.350(8) . ? C11 H11 0.9300 . ? C12 C13 1.385(7) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? B1 H1A 0.9800 . ? 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 C5 N1 C1 118.6(3) . . ? C5 N1 B1 123.3(3) . . ? C1 N1 B1 118.0(3) . . ? N1 C1 C2 121.9(4) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C3 C2 C1 118.2(4) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C4 C3 C2 120.5(3) . . ? C4 C3 Cl1 119.3(3) . . ? C2 C3 Cl1 120.3(3) . . ? C3 C4 C5 117.7(4) . . ? C3 C4 H4 121.2 . . ? C5 C4 H4 121.2 . . ? N1 C5 C4 123.0(3) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? N2 C6 B1 179.7(5) . . ? C8 C7 B1 114.1(3) . . ? C8 C7 H7A 108.7 . . ? B1 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? B1 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C13 C8 C9 116.2(4) . . ? C13 C8 C7 121.3(4) . . ? C9 C8 C7 122.5(4) . . ? C8 C9 C10 121.9(5) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C11 C10 C9 121.1(5) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 118.3(5) . . ? C10 C11 H11 120.9 . . ? C12 C11 H11 120.9 . . ? C11 C12 C13 121.2(5) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C8 C13 C12 121.3(5) . . ? C8 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C6 B1 N1 108.1(3) . . ? C6 B1 C7 112.6(3) . . ? N1 B1 C7 108.8(3) . . ? C6 B1 H1A 109.1 . . ? N1 B1 H1A 109.1 . . ? C7 B1 H1A 109.1 . . ? 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 C5 N1 C1 C2 -0.8(6) . . . . ? B1 N1 C1 C2 177.6(3) . . . . ? N1 C1 C2 C3 1.1(6) . . . . ? C1 C2 C3 C4 -0.5(6) . . . . ? C1 C2 C3 Cl1 178.5(3) . . . . ? C2 C3 C4 C5 -0.4(6) . . . . ? Cl1 C3 C4 C5 -179.4(3) . . . . ? C1 N1 C5 C4 -0.1(6) . . . . ? B1 N1 C5 C4 -178.4(4) . . . . ? C3 C4 C5 N1 0.7(6) . . . . ? B1 C7 C8 C13 -82.2(5) . . . . ? B1 C7 C8 C9 97.2(5) . . . . ? C13 C8 C9 C10 -1.3(7) . . . . ? C7 C8 C9 C10 179.3(4) . . . . ? C8 C9 C10 C11 0.6(8) . . . . ? C9 C10 C11 C12 0.2(8) . . . . ? C10 C11 C12 C13 -0.4(8) . . . . ? C9 C8 C13 C12 1.1(6) . . . . ? C7 C8 C13 C12 -179.5(4) . . . . ? C11 C12 C13 C8 -0.3(7) . . . . ? N2 C6 B1 N1 -164(100) . . . . ? N2 C6 B1 C7 75(100) . . . . ? C5 N1 B1 C6 -31.2(5) . . . . ? C1 N1 B1 C6 150.5(3) . . . . ? C5 N1 B1 C7 91.4(4) . . . . ? C1 N1 B1 C7 -86.9(4) . . . . ? C8 C7 B1 C6 -68.2(5) . . . . ? C8 C7 B1 N1 172.0(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.315 _refine_diff_density_min -0.494 _refine_diff_density_rms 0.066 data_lc104 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H17 B N2' _chemical_formula_weight 188.08 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+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.645(3) _cell_length_b 16.506(2) _cell_length_c 6.074(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1167.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.070 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _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 1202 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0801 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1202 _reflns_number_gt 645 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0749P)^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 SHELXL _refine_ls_extinction_coef 0.018(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(7) _refine_ls_number_reflns 1202 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1332 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1220 _refine_ls_wR_factor_gt 0.0950 _refine_ls_goodness_of_fit_ref 0.874 _refine_ls_restrained_S_all 0.874 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.6550(2) 0.21445(17) 0.0413(5) 0.0479(8) Uani 1 1 d . . . N2 N 0.8453(3) 0.2896(2) 0.4520(6) 0.0815(11) Uani 1 1 d . . . C1 C 0.9567(3) 0.0217(2) 0.1048(6) 0.0531(10) Uani 1 1 d . . . H1 H 0.9218 0.0139 -0.0312 0.064 Uiso 1 1 calc R . . C2 C 1.0657(3) -0.0077(2) 0.1400(8) 0.0648(11) Uani 1 1 d . . . H2 H 1.1032 -0.0360 0.0288 0.078 Uiso 1 1 calc R . . C3 C 1.1188(3) 0.0043(3) 0.3368(9) 0.0785(14) Uani 1 1 d . . . H3 H 1.1927 -0.0152 0.3606 0.094 Uiso 1 1 calc R . . C4 C 1.0621(4) 0.0455(3) 0.4991(9) 0.0798(14) Uani 1 1 d . . . H4 H 1.0980 0.0540 0.6339 0.096 Uiso 1 1 calc R . . C5 C 0.9530(3) 0.0744(2) 0.4657(7) 0.0607(11) Uani 1 1 d . . . H5 H 0.9160 0.1021 0.5784 0.073 Uiso 1 1 calc R . . C6 C 0.8978(3) 0.0630(2) 0.2692(6) 0.0458(9) Uani 1 1 d . . . C7 C 0.7781(3) 0.0939(2) 0.2278(7) 0.0548(10) Uani 1 1 d . . . H7A H 0.7352 0.0930 0.3646 0.066 Uiso 1 1 calc R . . H7B H 0.7397 0.0582 0.1246 0.066 Uiso 1 1 calc R . . C8 C 0.8164(3) 0.2468(2) 0.3159(7) 0.0550(11) Uani 1 1 d . . . C9 C 0.6620(3) 0.2991(2) -0.0404(7) 0.0708(12) Uani 1 1 d . . . H9A H 0.6853 0.3342 0.0776 0.085 Uiso 1 1 calc R . . H9B H 0.5882 0.3158 -0.0940 0.085 Uiso 1 1 calc R . . H9C H 0.7172 0.3022 -0.1576 0.085 Uiso 1 1 calc R . . C10 C 0.5660(3) 0.2104(3) 0.2150(7) 0.0763(13) Uani 1 1 d . . . H10A H 0.5887 0.2435 0.3374 0.092 Uiso 1 1 calc R . . H10B H 0.5572 0.1554 0.2630 0.092 Uiso 1 1 calc R . . H10C H 0.4943 0.2298 0.1573 0.092 Uiso 1 1 calc R . . C11 C 0.6188(3) 0.1626(3) -0.1448(7) 0.0824(14) Uani 1 1 d . . . H11A H 0.6755 0.1650 -0.2593 0.099 Uiso 1 1 calc R . . H11B H 0.5465 0.1815 -0.2008 0.099 Uiso 1 1 calc R . . H11C H 0.6109 0.1077 -0.0951 0.099 Uiso 1 1 calc R . . B1 B 0.7783(3) 0.1851(2) 0.1299(7) 0.0461(11) Uani 1 1 d . . . H1A H 0.8337 0.1880 0.0086 0.055 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 N1 0.0450(17) 0.0521(18) 0.0464(18) 0.0034(16) -0.0030(16) 0.0067(15) N2 0.088(3) 0.072(2) 0.084(3) -0.001(2) -0.018(3) -0.019(2) C1 0.056(2) 0.047(2) 0.057(2) 0.001(2) 0.000(2) -0.0090(18) C2 0.058(3) 0.055(2) 0.081(3) -0.001(3) 0.016(2) 0.004(2) C3 0.050(2) 0.070(3) 0.116(4) 0.010(3) -0.010(3) 0.019(2) C4 0.073(3) 0.085(3) 0.081(3) 0.007(3) -0.029(3) 0.014(3) C5 0.073(3) 0.060(2) 0.049(2) 0.005(2) -0.007(2) 0.011(2) C6 0.048(2) 0.0360(19) 0.054(2) 0.010(2) 0.001(2) 0.0010(17) C7 0.044(2) 0.050(2) 0.070(3) 0.009(2) -0.002(2) 0.0019(17) C8 0.050(2) 0.049(2) 0.065(3) 0.006(2) -0.006(2) -0.0082(18) C9 0.075(3) 0.059(3) 0.078(3) 0.015(2) -0.007(3) 0.015(2) C10 0.047(2) 0.103(3) 0.079(3) 0.023(3) 0.013(2) 0.016(2) C11 0.082(3) 0.089(3) 0.076(3) -0.016(3) -0.041(3) 0.015(2) B1 0.036(2) 0.052(2) 0.050(3) 0.005(2) 0.009(2) 0.0041(18) _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 C11 1.479(4) . ? N1 C10 1.480(4) . ? N1 C9 1.486(4) . ? N1 B1 1.608(4) . ? N2 C8 1.138(4) . ? C1 C2 1.376(5) . ? C1 C6 1.390(5) . ? C1 H1 0.9300 . ? C2 C3 1.360(5) . ? C2 H2 0.9300 . ? C3 C4 1.367(6) . ? C3 H3 0.9300 . ? C4 C5 1.372(5) . ? C4 H4 0.9300 . ? C5 C6 1.368(5) . ? C5 H5 0.9300 . ? C6 C7 1.505(5) . ? C7 B1 1.619(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 B1 1.584(6) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? B1 H1A 0.9800 . ? 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 C11 N1 C10 108.6(3) . . ? C11 N1 C9 107.7(3) . . ? C10 N1 C9 108.6(3) . . ? C11 N1 B1 109.6(3) . . ? C10 N1 B1 111.9(3) . . ? C9 N1 B1 110.2(3) . . ? C2 C1 C6 121.1(4) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? C3 C2 C1 120.3(4) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.1(4) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 C5 120.9(4) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 121.1(4) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 117.5(3) . . ? C5 C6 C7 122.3(4) . . ? C1 C6 C7 120.2(3) . . ? C6 C7 B1 112.0(3) . . ? C6 C7 H7A 109.2 . . ? B1 C7 H7A 109.2 . . ? C6 C7 H7B 109.2 . . ? B1 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? N2 C8 B1 178.3(4) . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 B1 N1 107.2(3) . . ? C8 B1 C7 109.6(3) . . ? N1 B1 C7 113.7(3) . . ? C8 B1 H1A 108.7 . . ? N1 B1 H1A 108.7 . . ? C7 B1 H1A 108.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.1(6) . . . . ? C1 C2 C3 C4 0.4(6) . . . . ? C2 C3 C4 C5 0.1(7) . . . . ? C3 C4 C5 C6 -0.1(6) . . . . ? C4 C5 C6 C1 -0.5(5) . . . . ? C4 C5 C6 C7 179.9(3) . . . . ? C2 C1 C6 C5 1.1(5) . . . . ? C2 C1 C6 C7 -179.3(3) . . . . ? C5 C6 C7 B1 89.4(4) . . . . ? C1 C6 C7 B1 -90.2(4) . . . . ? N2 C8 B1 N1 151(14) . . . . ? N2 C8 B1 C7 27(14) . . . . ? C11 N1 B1 C8 175.8(3) . . . . ? C10 N1 B1 C8 -63.6(4) . . . . ? C9 N1 B1 C8 57.3(4) . . . . ? C11 N1 B1 C7 -62.9(4) . . . . ? C10 N1 B1 C7 57.7(4) . . . . ? C9 N1 B1 C7 178.6(3) . . . . ? C6 C7 B1 C8 -70.8(4) . . . . ? C6 C7 B1 N1 169.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.133 _refine_diff_density_min -0.123 _refine_diff_density_rms 0.031