# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Russell, Christopher' _publ_contact_author_name 'Russell, Christopher' _publ_contact_author_email Chris.Russell@bristol.ac.uk _publ_section_title ; Boron-Nitrogen Analogues of the Fluorenyl Anion ; data_1 _database_code_depnum_ccdc_archive 'CCDC 767737' #TrackingRef '- merged.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 B Cl N2' _chemical_formula_sum 'C10 H8 B Cl N2' _chemical_formula_weight 202.44 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 3.84030(10) _cell_length_b 14.0971(4) _cell_length_c 16.9200(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.269(2) _cell_angle_gamma 90.00 _cell_volume 915.99(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5558 _cell_measurement_theta_min 2.808 _cell_measurement_theta_max 28.3015 _exptl_crystal_description Needle _exptl_crystal_colour Orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.368 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6264 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS-2008/1 - Bruker AXS' _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 'Bruker Kappa-APEX-II area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_reflns_number 14435 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2072 _reflns_number_gt 1799 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX-II (Bruker, 2004)' _computing_cell_refinement 'APEX-II and SAINT (Bruker, 2001)' _computing_data_reduction 'SAINT v7.51A (BRUKER)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0307P)^2^+0.4906P] 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 2072 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0761 _refine_ls_wR_factor_gt 0.0722 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 0.1425(4) 0.52675(10) 0.32070(9) 0.0170(3) Uani 1 1 d . . . Cl1 Cl 0.00776(10) 0.42221(2) 0.36915(2) 0.02273(11) Uani 1 1 d . . . N1 N 0.1059(3) 0.54781(8) 0.23905(7) 0.0154(2) Uani 1 1 d . . . N2 N 0.3130(3) 0.60617(8) 0.35510(7) 0.0153(2) Uani 1 1 d . . . C1 C -0.0499(4) 0.49787(10) 0.17730(8) 0.0183(3) Uani 1 1 d . . . H1 H -0.1507 0.4375 0.1872 0.022 Uiso 1 1 calc R . . C2 C -0.0594(4) 0.53421(10) 0.10363(8) 0.0201(3) Uani 1 1 d . . . H2 H -0.1677 0.4994 0.0622 0.024 Uiso 1 1 calc R . . C3 C 0.0929(4) 0.62516(10) 0.08709(8) 0.0196(3) Uani 1 1 d . . . H3 H 0.0875 0.6499 0.0349 0.024 Uiso 1 1 calc R . . C4 C 0.2446(4) 0.67563(9) 0.14632(8) 0.0174(3) Uani 1 1 d . . . H4 H 0.3450 0.7358 0.1355 0.021 Uiso 1 1 calc R . . C5 C 0.2538(3) 0.63894(9) 0.22422(8) 0.0151(3) Uani 1 1 d . . . C6 C 0.3801(3) 0.67417(9) 0.29473(8) 0.0146(3) Uani 1 1 d . . . C7 C 0.5485(4) 0.76026(9) 0.31544(8) 0.0169(3) Uani 1 1 d . . . H7 H 0.5993 0.8058 0.2758 0.020 Uiso 1 1 calc R . . C8 C 0.6375(4) 0.77766(10) 0.39189(9) 0.0200(3) Uani 1 1 d . . . H8 H 0.7461 0.8359 0.4058 0.024 Uiso 1 1 calc R . . C9 C 0.5672(4) 0.70793(10) 0.45169(8) 0.0193(3) Uani 1 1 d . . . H9 H 0.6316 0.7202 0.5050 0.023 Uiso 1 1 calc R . . C10 C 0.4111(4) 0.62541(10) 0.43282(8) 0.0179(3) Uani 1 1 d . . . H10 H 0.3673 0.5798 0.4729 0.021 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 0.0169(8) 0.0136(7) 0.0206(7) 0.0011(6) 0.0028(6) 0.0007(6) Cl1 0.0270(2) 0.01461(17) 0.02665(19) 0.00482(13) 0.00347(14) -0.00410(13) N1 0.0152(6) 0.0110(5) 0.0200(6) -0.0005(4) 0.0019(4) 0.0002(4) N2 0.0161(6) 0.0126(5) 0.0172(5) 0.0015(4) 0.0019(4) 0.0011(4) C1 0.0165(7) 0.0139(6) 0.0246(7) -0.0046(5) 0.0012(5) 0.0009(5) C2 0.0175(7) 0.0210(7) 0.0217(7) -0.0054(5) -0.0024(5) 0.0041(5) C3 0.0207(7) 0.0203(7) 0.0179(6) 0.0006(5) 0.0000(5) 0.0069(5) C4 0.0175(7) 0.0143(6) 0.0205(7) 0.0023(5) 0.0017(5) 0.0045(5) C5 0.0144(7) 0.0102(6) 0.0206(6) 0.0004(5) 0.0025(5) 0.0015(5) C6 0.0141(7) 0.0125(6) 0.0173(6) 0.0023(5) 0.0025(5) 0.0019(5) C7 0.0159(7) 0.0127(6) 0.0222(7) 0.0010(5) 0.0019(5) 0.0009(5) C8 0.0187(7) 0.0155(6) 0.0258(7) -0.0025(5) 0.0010(6) -0.0015(5) C9 0.0188(7) 0.0215(7) 0.0176(6) -0.0025(5) 0.0001(5) 0.0017(5) C10 0.0192(7) 0.0181(7) 0.0163(6) 0.0015(5) 0.0018(5) 0.0026(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 N1 1.4193(19) . ? B1 N2 1.4202(19) . ? B1 Cl1 1.7650(15) . ? N1 C1 1.3927(18) . ? N1 C5 1.4273(16) . ? N2 C10 1.3930(18) . ? N2 C6 1.4252(16) . ? C1 C2 1.348(2) . ? C1 H1 0.9500 . ? C2 C3 1.437(2) . ? C2 H2 0.9500 . ? C3 C4 1.358(2) . ? C3 H3 0.9500 . ? C4 C5 1.4161(18) . ? C4 H4 0.9500 . ? C5 C6 1.3785(19) . ? C6 C7 1.4183(19) . ? C7 C8 1.359(2) . ? C7 H7 0.9500 . ? C8 C9 1.4372(19) . ? C8 H8 0.9500 . ? C9 C10 1.346(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? 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 B1 N2 106.10(11) . . ? N1 B1 Cl1 126.78(11) . . ? N2 B1 Cl1 127.11(11) . . ? C1 N1 B1 131.66(12) . . ? C1 N1 C5 119.54(11) . . ? B1 N1 C5 108.77(11) . . ? C10 N2 B1 131.49(12) . . ? C10 N2 C6 119.77(11) . . ? B1 N2 C6 108.74(11) . . ? C2 C1 N1 120.74(13) . . ? C2 C1 H1 119.6 . . ? N1 C1 H1 119.6 . . ? C1 C2 C3 120.66(14) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 119.81(13) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.28(13) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 132.93(12) . . ? C6 C5 N1 108.10(11) . . ? C4 C5 N1 118.96(12) . . ? C5 C6 C7 132.86(12) . . ? C5 C6 N2 108.29(11) . . ? C7 C6 N2 118.84(12) . . ? C8 C7 C6 120.13(12) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 119.97(13) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.59(13) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 N2 120.69(12) . . ? C9 C10 H10 119.7 . . ? N2 C10 H10 119.7 . . ? 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 N2 B1 N1 C1 -177.65(13) . . . . ? Cl1 B1 N1 C1 3.1(2) . . . . ? N2 B1 N1 C5 0.18(15) . . . . ? Cl1 B1 N1 C5 -179.12(11) . . . . ? N1 B1 N2 C10 178.92(13) . . . . ? Cl1 B1 N2 C10 -1.8(2) . . . . ? N1 B1 N2 C6 -0.31(15) . . . . ? Cl1 B1 N2 C6 178.98(11) . . . . ? B1 N1 C1 C2 178.33(14) . . . . ? C5 N1 C1 C2 0.70(19) . . . . ? N1 C1 C2 C3 0.3(2) . . . . ? C1 C2 C3 C4 -0.7(2) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C3 C4 C5 C6 -178.39(14) . . . . ? C3 C4 C5 N1 0.90(19) . . . . ? C1 N1 C5 C6 178.16(11) . . . . ? B1 N1 C5 C6 0.02(15) . . . . ? C1 N1 C5 C4 -1.30(18) . . . . ? B1 N1 C5 C4 -179.43(12) . . . . ? C4 C5 C6 C7 -0.1(3) . . . . ? N1 C5 C6 C7 -179.49(14) . . . . ? C4 C5 C6 N2 179.13(14) . . . . ? N1 C5 C6 N2 -0.22(14) . . . . ? C10 N2 C6 C5 -179.00(11) . . . . ? B1 N2 C6 C5 0.33(15) . . . . ? C10 N2 C6 C7 0.38(18) . . . . ? B1 N2 C6 C7 179.72(12) . . . . ? C5 C6 C7 C8 178.01(14) . . . . ? N2 C6 C7 C8 -1.19(19) . . . . ? C6 C7 C8 C9 1.3(2) . . . . ? C7 C8 C9 C10 -0.5(2) . . . . ? C8 C9 C10 N2 -0.3(2) . . . . ? B1 N2 C10 C9 -178.81(14) . . . . ? C6 N2 C10 C9 0.36(19) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.302 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.048 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 767738' #TrackingRef '- merged.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H13 B N2' _chemical_formula_sum 'C16 H13 B N2' _chemical_formula_weight 244.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 20.144(2) _cell_length_b 17.3230(19) _cell_length_c 7.1036(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.577(2) _cell_angle_gamma 90.00 _cell_volume 2474.0(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5732 _cell_measurement_theta_min 2.345 _cell_measurement_theta_max 28.329 _exptl_crystal_description Plate _exptl_crystal_colour Red _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9453 _exptl_absorpt_correction_T_max 0.9985 _exptl_absorpt_process_details 'SADABS-2008/1 - Bruker AXS' _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 'Bruker Kappa-APEX-II area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24928 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.01 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5645 _reflns_number_gt 4049 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX-II (Bruker, 2004)' _computing_cell_refinement 'APEX-II and SAINT (Bruker, 2001)' _computing_data_reduction 'SAINT v7.51A (BRUKER)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0504P)^2^+0.5398P] 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 5645 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0708 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1055 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 0.48751(8) 0.66471(10) 0.6955(2) 0.0194(3) Uani 1 1 d . . . N1 N 0.44700(5) 0.73294(7) 0.70945(15) 0.0189(3) Uani 1 1 d . . . N2 N 0.44163(5) 0.60258(7) 0.72428(15) 0.0184(3) Uani 1 1 d . . . C1 C 0.46194(7) 0.81137(8) 0.69316(19) 0.0219(3) Uani 1 1 d . . . H1 H 0.5059 0.8265 0.6688 0.026 Uiso 1 1 calc R . . C2 C 0.41519(7) 0.86587(9) 0.7114(2) 0.0259(3) Uani 1 1 d . . . H2 H 0.4266 0.9187 0.6985 0.031 Uiso 1 1 calc R . . C3 C 0.34851(8) 0.84555(9) 0.7499(2) 0.0275(4) Uani 1 1 d . . . H3 H 0.3159 0.8845 0.7628 0.033 Uiso 1 1 calc R . . C4 C 0.33249(7) 0.76995(9) 0.76793(19) 0.0239(3) Uani 1 1 d . . . H4 H 0.2884 0.7559 0.7943 0.029 Uiso 1 1 calc R . . C5 C 0.38100(7) 0.71191(8) 0.74759(18) 0.0192(3) Uani 1 1 d . . . C6 C 0.37781(7) 0.63244(8) 0.75712(18) 0.0195(3) Uani 1 1 d . . . C7 C 0.32520(7) 0.58136(9) 0.79161(19) 0.0242(3) Uani 1 1 d . . . H7 H 0.2830 0.6014 0.8190 0.029 Uiso 1 1 calc R . . C8 C 0.33479(7) 0.50382(9) 0.7858(2) 0.0276(3) Uani 1 1 d . . . H8 H 0.2996 0.4695 0.8105 0.033 Uiso 1 1 calc R . . C9 C 0.39863(8) 0.47427(9) 0.7417(2) 0.0272(3) Uani 1 1 d . . . H9 H 0.4052 0.4201 0.7331 0.033 Uiso 1 1 calc R . . C10 C 0.44927(7) 0.52281(8) 0.71257(19) 0.0222(3) Uani 1 1 d . . . H10 H 0.4911 0.5022 0.6834 0.027 Uiso 1 1 calc R . . C11 C 0.56297(7) 0.65827(8) 0.66346(19) 0.0192(3) Uani 1 1 d . . . C12 C 0.60371(7) 0.60253(8) 0.75732(19) 0.0209(3) Uani 1 1 d . . . H12 H 0.5846 0.5683 0.8435 0.025 Uiso 1 1 calc R . . C13 C 0.67092(7) 0.59610(9) 0.7276(2) 0.0243(3) Uani 1 1 d . . . H13 H 0.6970 0.5574 0.7917 0.029 Uiso 1 1 calc R . . C14 C 0.70028(7) 0.64630(9) 0.6039(2) 0.0251(3) Uani 1 1 d . . . H14 H 0.7463 0.6420 0.5832 0.030 Uiso 1 1 calc R . . C15 C 0.66167(7) 0.70266(9) 0.5113(2) 0.0237(3) Uani 1 1 d . . . H15 H 0.6813 0.7374 0.4275 0.028 Uiso 1 1 calc R . . C16 C 0.59444(7) 0.70824(8) 0.54090(19) 0.0212(3) Uani 1 1 d . . . H16 H 0.5688 0.7471 0.4762 0.025 Uiso 1 1 calc R . . B2 B 0.01919(8) 0.67260(10) 0.3053(2) 0.0190(3) Uani 1 1 d . . . N3 N 0.05454(5) 0.74428(7) 0.33869(15) 0.0180(3) Uani 1 1 d . . . N4 N 0.06843(5) 0.61471(7) 0.35415(15) 0.0186(3) Uani 1 1 d . . . C17 C 0.03554(7) 0.82073(8) 0.30594(19) 0.0201(3) Uani 1 1 d . . . H17 H -0.0078 0.8316 0.2524 0.024 Uiso 1 1 calc R . . C18 C 0.07752(7) 0.87942(9) 0.3488(2) 0.0229(3) Uani 1 1 d . . . H18 H 0.0635 0.9310 0.3240 0.028 Uiso 1 1 calc R . . C19 C 0.14316(7) 0.86535(9) 0.4315(2) 0.0238(3) Uani 1 1 d . . . H19 H 0.1717 0.9072 0.4669 0.029 Uiso 1 1 calc R . . C20 C 0.16402(7) 0.79157(9) 0.45834(19) 0.0216(3) Uani 1 1 d . . . H20 H 0.2077 0.7816 0.5107 0.026 Uiso 1 1 calc R . . C21 C 0.12079(7) 0.72905(8) 0.40855(18) 0.0190(3) Uani 1 1 d . . . C22 C 0.12938(7) 0.65012(9) 0.41662(18) 0.0200(3) Uani 1 1 d . . . C23 C 0.18509(7) 0.60350(9) 0.47103(19) 0.0236(3) Uani 1 1 d . . . H23 H 0.2265 0.6270 0.5081 0.028 Uiso 1 1 calc R . . C24 C 0.17949(8) 0.52538(9) 0.4703(2) 0.0275(3) Uani 1 1 d . . . H24 H 0.2169 0.4941 0.5063 0.033 Uiso 1 1 calc R . . C25 C 0.11679(8) 0.49045(9) 0.4149(2) 0.0273(3) Uani 1 1 d . . . H25 H 0.1124 0.4359 0.4177 0.033 Uiso 1 1 calc R . . C26 C 0.06401(7) 0.53442(8) 0.3589(2) 0.0229(3) Uani 1 1 d . . . H26 H 0.0229 0.5102 0.3219 0.027 Uiso 1 1 calc R . . C27 C -0.05562(7) 0.66195(8) 0.24053(18) 0.0186(3) Uani 1 1 d . . . C28 C -0.10422(7) 0.71030(8) 0.31288(19) 0.0207(3) Uani 1 1 d . . . H28 H -0.0909 0.7487 0.4031 0.025 Uiso 1 1 calc R . . C29 C -0.17110(7) 0.70305(9) 0.2552(2) 0.0232(3) Uani 1 1 d . . . H29 H -0.2028 0.7365 0.3058 0.028 Uiso 1 1 calc R . . C30 C -0.19183(7) 0.64740(9) 0.1243(2) 0.0240(3) Uani 1 1 d . . . H30 H -0.2375 0.6428 0.0842 0.029 Uiso 1 1 calc R . . C31 C -0.14494(7) 0.59814(9) 0.0521(2) 0.0234(3) Uani 1 1 d . . . H31 H -0.1588 0.5594 -0.0366 0.028 Uiso 1 1 calc R . . C32 C -0.07824(7) 0.60556(8) 0.10934(19) 0.0209(3) Uani 1 1 d . . . H32 H -0.0469 0.5716 0.0586 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 0.0222(8) 0.0211(9) 0.0148(7) -0.0002(6) 0.0000(6) -0.0006(7) N1 0.0199(6) 0.0206(7) 0.0159(6) -0.0001(5) -0.0009(4) -0.0010(5) N2 0.0199(6) 0.0201(7) 0.0152(6) -0.0012(5) 0.0003(4) -0.0001(5) C1 0.0245(8) 0.0199(8) 0.0207(7) 0.0005(6) -0.0037(6) -0.0025(6) C2 0.0315(9) 0.0215(8) 0.0239(8) -0.0001(6) -0.0056(6) 0.0016(6) C3 0.0312(9) 0.0288(9) 0.0222(8) 0.0013(6) -0.0001(6) 0.0096(7) C4 0.0217(8) 0.0322(9) 0.0177(7) 0.0021(6) 0.0009(5) 0.0042(6) C5 0.0195(7) 0.0245(8) 0.0134(6) 0.0007(5) -0.0011(5) -0.0005(6) C6 0.0201(7) 0.0247(8) 0.0135(6) 0.0005(5) -0.0007(5) -0.0001(6) C7 0.0205(7) 0.0329(9) 0.0189(7) 0.0033(6) -0.0008(6) -0.0030(6) C8 0.0271(8) 0.0309(9) 0.0244(8) 0.0048(6) -0.0015(6) -0.0095(7) C9 0.0342(9) 0.0223(8) 0.0244(8) 0.0008(6) -0.0032(6) -0.0050(7) C10 0.0258(8) 0.0207(8) 0.0199(7) -0.0017(6) -0.0002(6) 0.0005(6) C11 0.0212(7) 0.0193(8) 0.0167(7) -0.0030(5) -0.0012(5) -0.0013(6) C12 0.0253(8) 0.0189(8) 0.0184(7) -0.0006(6) 0.0003(5) -0.0026(6) C13 0.0255(8) 0.0217(8) 0.0252(8) -0.0022(6) -0.0031(6) 0.0029(6) C14 0.0197(7) 0.0282(9) 0.0276(8) -0.0068(6) 0.0024(6) -0.0019(6) C15 0.0256(8) 0.0240(8) 0.0219(7) -0.0013(6) 0.0041(6) -0.0061(6) C16 0.0241(8) 0.0200(8) 0.0192(7) 0.0006(6) -0.0009(5) -0.0010(6) B2 0.0221(8) 0.0225(9) 0.0127(7) -0.0004(6) 0.0025(6) 0.0009(7) N3 0.0183(6) 0.0219(7) 0.0138(5) 0.0011(5) 0.0022(4) 0.0009(5) N4 0.0194(6) 0.0223(7) 0.0143(5) -0.0002(5) 0.0021(4) 0.0008(5) C17 0.0208(7) 0.0225(8) 0.0174(7) 0.0016(6) 0.0039(5) 0.0037(6) C18 0.0255(8) 0.0224(8) 0.0214(7) 0.0014(6) 0.0050(6) 0.0011(6) C19 0.0245(8) 0.0257(8) 0.0216(7) -0.0017(6) 0.0046(6) -0.0055(6) C20 0.0183(7) 0.0306(9) 0.0159(7) -0.0011(6) 0.0017(5) -0.0005(6) C21 0.0185(7) 0.0259(8) 0.0126(6) 0.0016(5) 0.0024(5) 0.0010(6) C22 0.0203(7) 0.0269(8) 0.0131(6) 0.0006(6) 0.0035(5) 0.0001(6) C23 0.0211(7) 0.0320(9) 0.0178(7) 0.0019(6) 0.0022(5) 0.0038(6) C24 0.0275(8) 0.0302(9) 0.0248(8) 0.0020(6) 0.0016(6) 0.0101(7) C25 0.0349(9) 0.0225(8) 0.0249(8) 0.0015(6) 0.0041(6) 0.0045(7) C26 0.0272(8) 0.0217(8) 0.0200(7) -0.0004(6) 0.0026(6) -0.0004(6) C27 0.0206(7) 0.0195(8) 0.0158(6) 0.0040(5) 0.0024(5) 0.0002(6) C28 0.0232(8) 0.0212(8) 0.0178(7) 0.0003(6) 0.0015(5) -0.0012(6) C29 0.0223(8) 0.0237(8) 0.0240(7) 0.0030(6) 0.0046(6) 0.0019(6) C30 0.0184(7) 0.0268(8) 0.0265(8) 0.0048(6) -0.0007(6) -0.0041(6) C31 0.0277(8) 0.0206(8) 0.0217(7) 0.0007(6) -0.0002(6) -0.0061(6) C32 0.0251(8) 0.0183(8) 0.0197(7) 0.0021(6) 0.0033(5) 0.0008(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 B1 N2 1.442(2) . ? B1 N1 1.443(2) . ? B1 C11 1.555(2) . ? N1 C1 1.3979(18) . ? N1 C5 1.4208(17) . ? N2 C10 1.3933(18) . ? N2 C6 1.4185(17) . ? C1 C2 1.345(2) . ? C1 H1 0.9500 . ? C2 C3 1.431(2) . ? C2 H2 0.9500 . ? C3 C4 1.357(2) . ? C3 H3 0.9500 . ? C4 C5 1.416(2) . ? C4 H4 0.9500 . ? C5 C6 1.380(2) . ? C6 C7 1.414(2) . ? C7 C8 1.358(2) . ? C7 H7 0.9500 . ? C8 C9 1.437(2) . ? C8 H8 0.9500 . ? C9 C10 1.348(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.406(2) . ? C11 C12 1.4078(19) . ? C12 C13 1.388(2) . ? C12 H12 0.9500 . ? C13 C14 1.394(2) . ? C13 H13 0.9500 . ? C14 C15 1.388(2) . ? C14 H14 0.9500 . ? C15 C16 1.387(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? B2 N4 1.438(2) . ? B2 N3 1.444(2) . ? B2 C27 1.559(2) . ? N3 C17 1.3941(18) . ? N3 C21 1.4192(17) . ? N4 C26 1.3944(19) . ? N4 C22 1.4185(17) . ? C17 C18 1.345(2) . ? C17 H17 0.9500 . ? C18 C19 1.434(2) . ? C18 H18 0.9500 . ? C19 C20 1.355(2) . ? C19 H19 0.9500 . ? C20 C21 1.421(2) . ? C20 H20 0.9500 . ? C21 C22 1.379(2) . ? C22 C23 1.417(2) . ? C23 C24 1.358(2) . ? C23 H23 0.9500 . ? C24 C25 1.433(2) . ? C24 H24 0.9500 . ? C25 C26 1.348(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C32 1.4062(19) . ? C27 C28 1.4095(19) . ? C28 C29 1.389(2) . ? C28 H28 0.9500 . ? C29 C30 1.385(2) . ? C29 H29 0.9500 . ? C30 C31 1.394(2) . ? C30 H30 0.9500 . ? C31 C32 1.3854(19) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? 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 N2 B1 N1 103.38(12) . . ? N2 B1 C11 127.47(13) . . ? N1 B1 C11 129.12(13) . . ? C1 N1 C5 118.28(12) . . ? C1 N1 B1 131.66(12) . . ? C5 N1 B1 110.06(12) . . ? C10 N2 C6 118.43(12) . . ? C10 N2 B1 131.13(12) . . ? C6 N2 B1 110.28(12) . . ? C2 C1 N1 121.23(14) . . ? C2 C1 H1 119.4 . . ? N1 C1 H1 119.4 . . ? C1 C2 C3 121.11(15) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 119.14(14) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 120.40(14) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 131.98(14) . . ? C6 C5 N1 108.19(12) . . ? C4 C5 N1 119.83(13) . . ? C5 C6 C7 132.11(14) . . ? C5 C6 N2 108.08(12) . . ? C7 C6 N2 119.81(13) . . ? C8 C7 C6 120.28(14) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 119.35(14) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C10 C9 C8 120.50(15) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 N2 121.47(14) . . ? C9 C10 H10 119.3 . . ? N2 C10 H10 119.3 . . ? C16 C11 C12 116.32(13) . . ? C16 C11 B1 121.92(12) . . ? C12 C11 B1 121.76(13) . . ? C13 C12 C11 121.91(14) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C12 C13 C14 120.14(14) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 119.37(14) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C16 C15 C14 120.04(14) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 122.22(13) . . ? C15 C16 H16 118.9 . . ? C11 C16 H16 118.9 . . ? N4 B2 N3 103.55(12) . . ? N4 B2 C27 128.94(13) . . ? N3 B2 C27 127.45(13) . . ? C17 N3 C21 118.51(12) . . ? C17 N3 B2 131.46(12) . . ? C21 N3 B2 109.95(12) . . ? C26 N4 C22 118.63(11) . . ? C26 N4 B2 131.10(12) . . ? C22 N4 B2 110.16(12) . . ? C18 C17 N3 121.20(13) . . ? C18 C17 H17 119.4 . . ? N3 C17 H17 119.4 . . ? C17 C18 C19 121.00(14) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C20 C19 C18 119.21(14) . . ? C20 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? C19 C20 C21 120.27(13) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C22 C21 N3 108.15(12) . . ? C22 C21 C20 132.25(13) . . ? N3 C21 C20 119.59(13) . . ? C21 C22 C23 132.19(14) . . ? C21 C22 N4 108.18(12) . . ? C23 C22 N4 119.63(13) . . ? C24 C23 C22 120.18(14) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 119.57(14) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C26 C25 C24 120.52(15) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 N4 121.37(14) . . ? C25 C26 H26 119.3 . . ? N4 C26 H26 119.3 . . ? C32 C27 C28 116.79(12) . . ? C32 C27 B2 123.03(13) . . ? C28 C27 B2 120.18(12) . . ? C29 C28 C27 121.45(13) . . ? C29 C28 H28 119.3 . . ? C27 C28 H28 119.3 . . ? C30 C29 C28 120.45(14) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C29 C30 C31 119.35(13) . . ? C29 C30 H30 120.3 . . ? C31 C30 H30 120.3 . . ? C32 C31 C30 120.13(14) . . ? C32 C31 H31 119.9 . . ? C30 C31 H31 119.9 . . ? C31 C32 C27 121.83(14) . . ? C31 C32 H32 119.1 . . ? C27 C32 H32 119.1 . . ? 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 N2 B1 N1 C1 -179.44(13) . . . . ? C11 B1 N1 C1 2.3(2) . . . . ? N2 B1 N1 C5 0.90(14) . . . . ? C11 B1 N1 C5 -177.36(13) . . . . ? N1 B1 N2 C10 174.22(12) . . . . ? C11 B1 N2 C10 -7.5(2) . . . . ? N1 B1 N2 C6 -1.06(14) . . . . ? C11 B1 N2 C6 177.24(13) . . . . ? C5 N1 C1 C2 -0.53(19) . . . . ? B1 N1 C1 C2 179.83(13) . . . . ? N1 C1 C2 C3 0.6(2) . . . . ? C1 C2 C3 C4 -0.1(2) . . . . ? C2 C3 C4 C5 -0.4(2) . . . . ? C3 C4 C5 C6 -179.35(14) . . . . ? C3 C4 C5 N1 0.4(2) . . . . ? C1 N1 C5 C6 179.86(11) . . . . ? B1 N1 C5 C6 -0.43(15) . . . . ? C1 N1 C5 C4 0.02(18) . . . . ? B1 N1 C5 C4 179.73(12) . . . . ? C4 C5 C6 C7 -0.5(3) . . . . ? N1 C5 C6 C7 179.73(13) . . . . ? C4 C5 C6 N2 179.56(13) . . . . ? N1 C5 C6 N2 -0.26(14) . . . . ? C10 N2 C6 C5 -175.11(11) . . . . ? B1 N2 C6 C5 0.85(15) . . . . ? C10 N2 C6 C7 4.90(18) . . . . ? B1 N2 C6 C7 -179.14(12) . . . . ? C5 C6 C7 C8 177.31(14) . . . . ? N2 C6 C7 C8 -2.7(2) . . . . ? C6 C7 C8 C9 -0.8(2) . . . . ? C7 C8 C9 C10 2.2(2) . . . . ? C8 C9 C10 N2 0.1(2) . . . . ? C6 N2 C10 C9 -3.61(19) . . . . ? B1 N2 C10 C9 -178.58(14) . . . . ? N2 B1 C11 C16 143.79(14) . . . . ? N1 B1 C11 C16 -38.3(2) . . . . ? N2 B1 C11 C12 -36.9(2) . . . . ? N1 B1 C11 C12 140.96(15) . . . . ? C16 C11 C12 C13 -1.3(2) . . . . ? B1 C11 C12 C13 179.32(13) . . . . ? C11 C12 C13 C14 0.9(2) . . . . ? C12 C13 C14 C15 0.1(2) . . . . ? C13 C14 C15 C16 -0.5(2) . . . . ? C14 C15 C16 C11 0.1(2) . . . . ? C12 C11 C16 C15 0.9(2) . . . . ? B1 C11 C16 C15 -179.80(13) . . . . ? N4 B2 N3 C17 175.08(12) . . . . ? C27 B2 N3 C17 -7.4(2) . . . . ? N4 B2 N3 C21 -1.49(14) . . . . ? C27 B2 N3 C21 175.98(13) . . . . ? N3 B2 N4 C26 177.06(13) . . . . ? C27 B2 N4 C26 -0.4(2) . . . . ? N3 B2 N4 C22 1.06(14) . . . . ? C27 B2 N4 C22 -176.36(13) . . . . ? C21 N3 C17 C18 -3.61(19) . . . . ? B2 N3 C17 C18 -179.95(14) . . . . ? N3 C17 C18 C19 -0.6(2) . . . . ? C17 C18 C19 C20 3.1(2) . . . . ? C18 C19 C20 C21 -1.2(2) . . . . ? C17 N3 C21 C22 -175.67(11) . . . . ? B2 N3 C21 C22 1.41(15) . . . . ? C17 N3 C21 C20 5.36(18) . . . . ? B2 N3 C21 C20 -177.56(12) . . . . ? C19 C20 C21 C22 178.37(14) . . . . ? C19 C20 C21 N3 -2.9(2) . . . . ? N3 C21 C22 C23 178.55(14) . . . . ? C20 C21 C22 C23 -2.7(3) . . . . ? N3 C21 C22 N4 -0.70(14) . . . . ? C20 C21 C22 N4 178.09(14) . . . . ? C26 N4 C22 C21 -176.82(12) . . . . ? B2 N4 C22 C21 -0.25(15) . . . . ? C26 N4 C22 C23 3.82(18) . . . . ? B2 N4 C22 C23 -179.62(12) . . . . ? C21 C22 C23 C24 178.29(14) . . . . ? N4 C22 C23 C24 -2.5(2) . . . . ? C22 C23 C24 C25 -0.3(2) . . . . ? C23 C24 C25 C26 1.8(2) . . . . ? C24 C25 C26 N4 -0.4(2) . . . . ? C22 N4 C26 C25 -2.4(2) . . . . ? B2 N4 C26 C25 -178.09(14) . . . . ? N4 B2 C27 C32 -43.0(2) . . . . ? N3 B2 C27 C32 140.16(15) . . . . ? N4 B2 C27 C28 137.39(15) . . . . ? N3 B2 C27 C28 -39.4(2) . . . . ? C32 C27 C28 C29 -0.8(2) . . . . ? B2 C27 C28 C29 178.84(13) . . . . ? C27 C28 C29 C30 0.2(2) . . . . ? C28 C29 C30 C31 0.6(2) . . . . ? C29 C30 C31 C32 -0.7(2) . . . . ? C30 C31 C32 C27 0.1(2) . . . . ? C28 C27 C32 C31 0.6(2) . . . . ? B2 C27 C32 C31 -178.99(13) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.298 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.044