# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr Chi-ming Che' _publ_contact_author_address ; Department of Chemistry The University of Hong Kong Pokfulam Road HONG KONG ; _publ_contact_author_email CMCHE@HKU.HK _publ_section_title ; Borazine Materials for Organic Optoelectronic Applications ; loop_ _publ_author_name 'Chi-ming Che.' 'Chi-Chung Kwok.' 'Iona H. T. Sham' 'Nianyong Zhu.' data_mar1085a _database_code_depnum_ccdc_archive 'CCDC 232653' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H33 B3 N6' _chemical_formula_sum 'C36 H33 B3 N6' _chemical_formula_weight 582.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 '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' 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' _symmetry_cell_setting rhombohedral _symmetry_space_group_name_H-M 'R -3 c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'y, x, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'y+2/3, x+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' 'y+1/3, x+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-y, -x, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-y+2/3, -x+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' '-y+1/3, -x+2/3, z+1/6' _cell_length_a 14.818(2) _cell_length_b 14.818(2) _cell_length_c 24.856(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4726.5(13) _cell_formula_units_Z 6 _cell_measurement_temperature 253(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1836 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 253(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 'marresearch IPDS mar300' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5591 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.29 _reflns_number_total 917 _reflns_number_gt 738 _reflns_threshold_expression >2sigma(I) _computing_data_collection Marcontrol _computing_cell_refinement Scalepack _computing_data_reduction Denzo _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0685P)^2^+0.4003P] 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 0.0035(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 917 _refine_ls_number_parameters 73 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1037 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 N1 N 0.0000 -0.09491(10) 0.2500 0.0330(4) Uani 1 2 d S . . N2 N 0.19532(8) 0.0000 0.2500 0.0331(4) Uani 1 2 d S . . B1 B 0.09792(12) 0.0000 0.2500 0.0304(5) Uani 1 2 d S . . C1 C 0.29341(9) 0.09344(8) 0.25758(5) 0.0319(4) Uani 1 1 d . . . C2 C 0.31118(10) 0.15553(10) 0.30284(5) 0.0387(4) Uani 1 1 d . . . H2 H 0.2599 0.1350 0.3291 0.046 Uiso 1 1 calc R . . C3 C 0.40452(10) 0.24737(10) 0.30893(6) 0.0457(4) Uani 1 1 d . . . H3 H 0.4151 0.2889 0.3390 0.055 Uiso 1 1 calc R . . C4 C 0.48235(11) 0.27813(10) 0.27078(6) 0.0479(4) Uani 1 1 d . . . H4 H 0.5451 0.3402 0.2749 0.058 Uiso 1 1 calc R . . C5 C 0.46571(10) 0.21547(10) 0.22643(5) 0.0461(4) Uani 1 1 d . . . H5 H 0.5181 0.2350 0.2009 0.055 Uiso 1 1 calc R . . C6 C 0.37227(9) 0.12437(10) 0.21965(5) 0.0382(4) Uani 1 1 d . . . H6 H 0.3619 0.0833 0.1894 0.046 Uiso 1 1 calc R . . H1 H 0.0000 -0.1521(14) 0.2500 0.045(5) Uiso 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0280(8) 0.0244(6) 0.0478(9) -0.0005(3) -0.0009(6) 0.0140(4) N2 0.0257(6) 0.0260(8) 0.0476(9) -0.0063(6) -0.0031(3) 0.0130(4) B1 0.0294(8) 0.0308(10) 0.0314(10) -0.0011(7) -0.0006(3) 0.0154(5) C1 0.0278(7) 0.0280(7) 0.0428(7) -0.0025(5) -0.0048(5) 0.0160(5) C2 0.0302(7) 0.0385(7) 0.0477(8) -0.0076(5) -0.0017(5) 0.0174(6) C3 0.0386(8) 0.0386(8) 0.0588(9) -0.0153(6) -0.0084(6) 0.0186(6) C4 0.0324(8) 0.0317(7) 0.0706(10) -0.0031(6) -0.0052(6) 0.0092(6) C5 0.0335(7) 0.0419(8) 0.0561(9) 0.0053(6) 0.0072(6) 0.0137(6) C6 0.0350(7) 0.0383(7) 0.0413(7) -0.0025(5) -0.0007(5) 0.0183(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 N1 B1 1.4292(12) . ? N1 B1 1.4292(12) 3 ? N2 C1 1.4327(13) . ? N2 C1 1.4327(13) 4 ? N2 B1 1.443(2) . ? B1 N1 1.4292(12) 2 ? C1 C6 1.3888(17) . ? C1 C2 1.3925(17) . ? C2 C3 1.3805(18) . ? C3 C4 1.382(2) . ? C4 C5 1.382(2) . ? C5 C6 1.3779(17) . ? 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 B1 N1 B1 123.09(16) . 3 ? C1 N2 C1 115.82(12) . 4 ? C1 N2 B1 122.09(6) . . ? C1 N2 B1 122.09(6) 4 . ? N1 B1 N1 116.91(16) . 2 ? N1 B1 N2 121.55(8) . . ? N1 B1 N2 121.55(8) 2 . ? C6 C1 C2 118.71(11) . . ? C6 C1 N2 120.62(10) . . ? C2 C1 N2 120.67(10) . . ? C3 C2 C1 120.34(12) . . ? C2 C3 C4 120.62(12) . . ? C5 C4 C3 119.11(12) . . ? C6 C5 C4 120.67(12) . . ? C5 C6 C1 120.52(11) . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 25.29 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.211 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.066 data_new _database_code_depnum_ccdc_archive 'CCDC 232654' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H18 B3 N3' _chemical_formula_sum 'C18 H18 B3 N3' _chemical_formula_weight 308.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 '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' 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 7.904(2) _cell_length_b 19.879(4) _cell_length_c 10.989(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1726.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 253(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 253(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 'marresearch IPDS mar300' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4355 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0691 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 24.45 _reflns_number_total 1707 _reflns_number_gt 1224 _reflns_threshold_expression >2sigma(I) _computing_data_collection Marcontrol _computing_cell_refinement Scalepack _computing_data_reduction Denzo _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0539P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(3) _refine_ls_number_reflns 1707 _refine_ls_number_parameters 217 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.940 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.7144(3) 0.11089(14) 0.4589(3) 0.0448(9) Uani 1 1 d . . . N2 N 0.7464(3) 0.23418(14) 0.4576(3) 0.0463(9) Uani 1 1 d . . . N3 N 0.7830(3) 0.17199(13) 0.6487(3) 0.0442(8) Uani 1 1 d . . . B1 B 0.7156(5) 0.17313(19) 0.3927(5) 0.0452(12) Uani 1 1 d . . . H1 H 0.6966 0.1737 0.3092 0.054 Uiso 1 1 calc R . . B2 B 0.7817(6) 0.2342(2) 0.5845(5) 0.0491(13) Uani 1 1 d . . . H2 H 0.8037 0.2743 0.6250 0.059 Uiso 1 1 calc R . . B3 B 0.7513(5) 0.1100(2) 0.5861(5) 0.0482(12) Uani 1 1 d . . . H3 H 0.7548 0.0694 0.6282 0.058 Uiso 1 1 calc R . . C1 C 0.6772(5) 0.04926(17) 0.3976(4) 0.0477(10) Uani 1 1 d . . . C2 C 0.5700(4) 0.00205(18) 0.4514(4) 0.0581(11) Uani 1 1 d . . . H2A H 0.5233 0.0102 0.5277 0.070 Uiso 1 1 calc R . . C3 C 0.5337(6) -0.05759(19) 0.3896(5) 0.0713(13) Uani 1 1 d . . . H3A H 0.4622 -0.0892 0.4249 0.086 Uiso 1 1 calc R . . C4 C 0.6015(6) -0.0699(2) 0.2787(6) 0.0750(15) Uani 1 1 d . . . H4 H 0.5758 -0.1098 0.2386 0.090 Uiso 1 1 calc R . . C5 C 0.7070(6) -0.0244(2) 0.2249(5) 0.0671(13) Uani 1 1 d . . . H5 H 0.7533 -0.0334 0.1489 0.081 Uiso 1 1 calc R . . C6 C 0.7448(5) 0.0348(2) 0.2836(4) 0.0589(12) Uani 1 1 d . . . H6 H 0.8166 0.0657 0.2465 0.071 Uiso 1 1 calc R . . C7 C 0.7447(4) 0.29736(17) 0.3918(4) 0.0468(11) Uani 1 1 d . . . C8 C 0.8243(5) 0.30288(19) 0.2816(5) 0.0617(12) Uani 1 1 d . . . H8 H 0.8811 0.2659 0.2496 0.074 Uiso 1 1 calc R . . C9 C 0.8212(6) 0.3631(3) 0.2166(5) 0.0769(14) Uani 1 1 d . . . H9 H 0.8731 0.3662 0.1409 0.092 Uiso 1 1 calc R . . C10 C 0.7405(6) 0.4176(2) 0.2659(6) 0.0818(17) Uani 1 1 d . . . H10 H 0.7393 0.4581 0.2237 0.098 Uiso 1 1 calc R . . C11 C 0.6622(6) 0.4132(2) 0.3755(5) 0.0721(14) Uani 1 1 d . . . H11 H 0.6076 0.4507 0.4077 0.087 Uiso 1 1 calc R . . C12 C 0.6633(5) 0.35290(18) 0.4400(4) 0.0598(12) Uani 1 1 d . . . H12 H 0.6095 0.3500 0.5151 0.072 Uiso 1 1 calc R . . C13 C 0.8223(4) 0.17045(17) 0.7768(4) 0.0428(9) Uani 1 1 d . . . C14 C 0.7423(5) 0.21238(17) 0.8579(4) 0.0549(12) Uani 1 1 d . . . H14 H 0.6598 0.2421 0.8302 0.066 Uiso 1 1 calc R . . C15 C 0.7829(6) 0.21088(19) 0.9797(4) 0.0647(13) Uani 1 1 d . . . H15 H 0.7288 0.2398 1.0336 0.078 Uiso 1 1 calc R . . C16 C 0.9047(6) 0.1663(2) 1.0225(4) 0.0643(12) Uani 1 1 d . . . H16 H 0.9322 0.1653 1.1047 0.077 Uiso 1 1 calc R . . C17 C 0.9832(5) 0.12398(19) 0.9429(4) 0.0642(12) Uani 1 1 d . . . H17 H 1.0633 0.0935 0.9712 0.077 Uiso 1 1 calc R . . C18 C 0.9443(5) 0.12613(19) 0.8195(4) 0.0554(12) Uani 1 1 d . . . H18 H 1.0002 0.0978 0.7655 0.066 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 0.058(2) 0.036(2) 0.041(3) 0.0002(16) -0.0017(17) -0.0025(14) N2 0.0571(19) 0.036(2) 0.046(3) 0.0071(16) -0.0012(18) 0.0025(14) N3 0.0618(19) 0.0337(18) 0.037(2) -0.0002(16) 0.0016(17) -0.0024(14) B1 0.050(3) 0.043(3) 0.042(3) -0.004(2) -0.001(2) -0.0020(19) B2 0.066(3) 0.036(3) 0.045(4) -0.002(2) 0.000(2) -0.005(2) B3 0.055(3) 0.042(3) 0.047(4) 0.005(2) 0.002(2) 0.002(2) C1 0.057(2) 0.040(2) 0.047(3) -0.006(2) -0.004(2) 0.002(2) C2 0.067(3) 0.046(2) 0.061(3) -0.005(2) -0.001(2) -0.007(2) C3 0.076(3) 0.046(3) 0.092(4) -0.005(3) -0.018(3) -0.007(2) C4 0.087(3) 0.054(3) 0.085(4) -0.032(3) -0.040(4) 0.018(3) C5 0.074(3) 0.066(3) 0.062(4) -0.023(3) -0.015(3) 0.015(2) C6 0.058(3) 0.059(3) 0.059(4) -0.002(3) -0.006(2) 0.005(2) C7 0.052(2) 0.044(2) 0.045(3) 0.008(2) -0.007(2) -0.007(2) C8 0.069(3) 0.057(3) 0.059(3) 0.007(3) -0.008(3) -0.010(2) C9 0.096(3) 0.076(3) 0.059(3) 0.027(3) -0.011(3) -0.025(3) C10 0.100(4) 0.048(3) 0.098(5) 0.031(3) -0.034(4) -0.015(3) C11 0.076(3) 0.046(3) 0.095(5) 0.011(3) -0.015(3) 0.001(2) C12 0.066(3) 0.043(2) 0.070(4) 0.005(2) 0.000(2) -0.003(2) C13 0.055(2) 0.037(2) 0.037(3) 0.006(2) 0.003(2) -0.003(2) C14 0.071(3) 0.045(3) 0.049(4) -0.002(2) -0.003(2) 0.009(2) C15 0.081(3) 0.066(3) 0.047(4) -0.010(2) 0.004(3) -0.001(2) C16 0.085(3) 0.072(3) 0.036(3) 0.005(2) -0.008(3) 0.002(3) C17 0.072(3) 0.056(3) 0.065(4) 0.007(3) -0.011(3) 0.009(2) C18 0.068(3) 0.057(3) 0.041(3) -0.002(2) 0.004(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 N1 C1 1.428(5) . ? N1 B3 1.429(6) . ? N1 B1 1.435(5) . ? N2 B2 1.421(5) . ? N2 B1 1.429(5) . ? N2 C7 1.449(5) . ? N3 B2 1.424(5) . ? N3 B3 1.433(5) . ? N3 C13 1.442(5) . ? C1 C6 1.393(6) . ? C1 C2 1.395(5) . ? C2 C3 1.396(5) . ? C3 C4 1.353(7) . ? C4 C5 1.365(6) . ? C5 C6 1.374(6) . ? C7 C8 1.369(6) . ? C7 C12 1.383(5) . ? C8 C9 1.394(6) . ? C9 C10 1.369(7) . ? C10 C11 1.357(7) . ? C11 C12 1.393(6) . ? C13 C14 1.374(5) . ? C13 C18 1.388(5) . ? C14 C15 1.377(5) . ? C15 C16 1.390(6) . ? C16 C17 1.363(5) . ? C17 C18 1.391(5) . ? 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 C1 N1 B3 119.5(3) . . ? C1 N1 B1 120.1(4) . . ? B3 N1 B1 120.4(3) . . ? B2 N2 B1 121.6(3) . . ? B2 N2 C7 119.4(3) . . ? B1 N2 C7 119.0(3) . . ? B2 N3 B3 120.5(4) . . ? B2 N3 C13 120.3(3) . . ? B3 N3 C13 119.2(3) . . ? N2 B1 N1 118.7(4) . . ? N2 B2 N3 119.2(4) . . ? N1 B3 N3 119.7(4) . . ? C6 C1 C2 118.4(4) . . ? C6 C1 N1 121.5(3) . . ? C2 C1 N1 120.2(4) . . ? C1 C2 C3 119.3(5) . . ? C4 C3 C2 120.7(4) . . ? C3 C4 C5 120.8(4) . . ? C4 C5 C6 119.8(5) . . ? C5 C6 C1 121.0(4) . . ? C8 C7 C12 119.2(4) . . ? C8 C7 N2 120.4(3) . . ? C12 C7 N2 120.3(4) . . ? C7 C8 C9 120.9(4) . . ? C10 C9 C8 119.0(5) . . ? C11 C10 C9 120.9(5) . . ? C10 C11 C12 120.2(4) . . ? C7 C12 C11 119.7(4) . . ? C14 C13 C18 119.1(4) . . ? C14 C13 N3 121.4(3) . . ? C18 C13 N3 119.6(4) . . ? C13 C14 C15 120.6(4) . . ? C14 C15 C16 120.3(4) . . ? C17 C16 C15 119.5(4) . . ? C16 C17 C18 120.4(4) . . ? C13 C18 C17 120.2(4) . . ? _diffrn_measured_fraction_theta_max 0.724 _diffrn_reflns_theta_full 24.45 _diffrn_measured_fraction_theta_full 0.724 _refine_diff_density_max 0.161 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.042