# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_publication_text _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_section_title 'New Polycyclic Borazine Species' _publ_contact_author_name 'Chris Russell' _publ_contact_author_address ;School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS ; _publ_contact_author_email Chris.Russell@bris.ac.uk _publ_contact_author_phone '+44 (0)117 928 7599' _publ_contact_author_fax '+44 (0)117 925 1295 ' loop_ _publ_author_name _publ_author_address C.Russell ;School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS ; X.Xie ;School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS ; S.M.Mansell ;School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS ; M.Haddow ;School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS ; N.C.Norman ;School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS ; data_3 _database_code_depnum_ccdc_archive 'CCDC 807912' #TrackingRef '- Combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H32 B6 N8, C7 H8' _chemical_formula_sum 'C27 H40 B6 N8' _chemical_formula_weight 541.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 _symmetry_space_group_name_Hall '-C 2yc' 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 27.515(5) _cell_length_b 12.652(2) _cell_length_c 8.8516(14) _cell_angle_alpha 90.00 _cell_angle_beta 102.852(9) _cell_angle_gamma 90.00 _cell_volume 3004.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2013 _cell_measurement_theta_min 3.30 _cell_measurement_theta_max 58.64 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.01 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_max 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.544 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4858 _exptl_absorpt_correction_T_max 0.7515 _exptl_absorpt_process_details 'SADABS V2008/1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Microstar CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7746 _diffrn_reflns_av_R_equivalents 0.0672 _diffrn_reflns_av_sigmaI/netI 0.0665 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 58.97 _reflns_number_total 2129 _reflns_number_gt 1616 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker PROTEUM' _computing_cell_refinement 'Bruker PROTEUM' _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^)+(0.0632P)^2^+2.8389P] 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 2129 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0731 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1351 _refine_ls_wR_factor_gt 0.1223 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.22166(11) 0.2694(2) 0.9687(3) 0.0216(6) Uani 1 1 d . . . B2 B 0.20921(11) 0.1419(2) 0.7605(3) 0.0223(7) Uani 1 1 d . . . B3 B 0.22570(11) 0.3564(2) 1.2168(3) 0.0224(7) Uani 1 1 d . . . N1 N 0.18881(7) 0.23616(15) 0.8284(2) 0.0205(5) Uani 1 1 d . . . N2 N 0.19696(7) 0.33944(14) 1.0543(2) 0.0200(5) Uani 1 1 d . . . N3 N 0.17904(8) 0.05565(15) 0.7004(2) 0.0249(5) Uani 1 1 d . . . N4 N 0.20170(8) 0.35519(15) 1.3409(2) 0.0242(5) Uani 1 1 d . . . C1 C 0.14921(9) 0.35466(18) 0.9607(2) 0.0207(6) Uani 1 1 d . . . C2 C 0.14403(9) 0.29227(18) 0.8228(3) 0.0211(6) Uani 1 1 d . . . C3 C 0.10155(9) 0.30165(19) 0.7065(3) 0.0249(6) Uani 1 1 d . . . H3 H 0.0979 0.2612 0.6142 0.030 Uiso 1 1 calc R . . C4 C 0.06438(10) 0.3707(2) 0.7260(3) 0.0287(6) Uani 1 1 d . . . H4 H 0.0349 0.3769 0.6467 0.034 Uiso 1 1 calc R . . C5 C 0.06945(10) 0.43102(19) 0.8597(3) 0.0273(6) Uani 1 1 d . . . H5 H 0.0435 0.4779 0.8703 0.033 Uiso 1 1 calc R . . C6 C 0.11179(9) 0.42386(19) 0.9776(3) 0.0248(6) Uani 1 1 d . . . H6 H 0.1151 0.4657 1.0685 0.030 Uiso 1 1 calc R . . C7 C 0.19878(11) -0.0401(2) 0.6422(3) 0.0304(7) Uani 1 1 d . . . H7A H 0.2350 -0.0337 0.6562 0.046 Uiso 1 1 calc R . . H7B H 0.1835 -0.0488 0.5318 0.046 Uiso 1 1 calc R . . H7C H 0.1910 -0.1017 0.6996 0.046 Uiso 1 1 calc R . . C8 C 0.12629(10) 0.0444(2) 0.6986(3) 0.0327(7) Uani 1 1 d . . . H8A H 0.1160 0.1011 0.7601 0.049 Uiso 1 1 calc R . . H8B H 0.1205 -0.0242 0.7429 0.049 Uiso 1 1 calc R . . H8C H 0.1069 0.0487 0.5916 0.049 Uiso 1 1 calc R . . C9 C 0.15031(10) 0.3233(2) 1.3295(3) 0.0300(6) Uani 1 1 d . . . H9A H 0.1358 0.3001 1.2234 0.045 Uiso 1 1 calc R . . H9B H 0.1312 0.3832 1.3558 0.045 Uiso 1 1 calc R . . H9C H 0.1493 0.2650 1.4016 0.045 Uiso 1 1 calc R . . C10 C 0.22730(10) 0.3754(2) 1.5010(3) 0.0289(6) Uani 1 1 d . . . H10A H 0.2632 0.3807 1.5077 0.043 Uiso 1 1 calc R . . H10B H 0.2207 0.3173 1.5669 0.043 Uiso 1 1 calc R . . H10C H 0.2152 0.4418 1.5361 0.043 Uiso 1 1 calc R . . C17 C 0.9617(2) 0.1689(5) 0.4992(7) 0.0430(15) Uani 0.50 1 d P A -1 H17A H 0.9872 0.1848 0.5928 0.065 Uiso 0.50 1 calc PR A -1 H17B H 0.9505 0.0957 0.5038 0.065 Uiso 0.50 1 calc PR A -1 H17C H 0.9334 0.2169 0.4925 0.065 Uiso 0.50 1 calc PR A -1 C11 C 0.9835(4) 0.1829(6) 0.3581(9) 0.034(2) Uani 0.50 1 d PG A -1 C12 C 0.9941(8) 0.2840(4) 0.3130(17) 0.039(4) Uani 0.50 1 d PG A -1 H12 H 0.9872 0.3437 0.3699 0.046 Uiso 0.50 1 calc PR A -1 C13 C 1.0147(8) 0.2978(3) 0.1845(18) 0.036(3) Uani 0.50 1 d PG A -1 H13 H 1.0219 0.3669 0.1537 0.043 Uiso 0.50 1 calc PR A -1 C14 C 1.0247(4) 0.2105(6) 0.1011(10) 0.037(2) Uani 0.50 1 d PG A -1 H14 H 1.0388 0.2199 0.0133 0.045 Uiso 0.50 1 calc PR A -1 C15 C 1.0142(2) 0.1094(4) 0.1463(6) 0.041(2) Uani 0.50 1 d PG A -1 H15 H 1.0210 0.0497 0.0893 0.049 Uiso 0.50 1 calc PR A -1 C16 C 0.9936(2) 0.0956(4) 0.2747(7) 0.036(3) Uani 0.50 1 d PG A -1 H16 H 0.9863 0.0265 0.3055 0.043 Uiso 0.50 1 calc PR A -1 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 0.0385(17) 0.0124(14) 0.0174(13) 0.0010(11) 0.0137(12) -0.0036(13) B2 0.0438(18) 0.0154(15) 0.0087(12) 0.0015(11) 0.0080(12) -0.0003(13) B3 0.0451(18) 0.0062(14) 0.0178(13) -0.0005(11) 0.0112(13) 0.0008(13) N1 0.0309(12) 0.0159(11) 0.0166(9) -0.0001(8) 0.0092(8) 0.0006(9) N2 0.0323(12) 0.0125(11) 0.0172(10) -0.0008(8) 0.0102(9) -0.0005(9) N3 0.0391(13) 0.0169(12) 0.0199(10) -0.0044(8) 0.0093(9) -0.0022(10) N4 0.0391(13) 0.0183(11) 0.0184(10) 0.0002(8) 0.0133(9) 0.0022(10) C1 0.0295(14) 0.0155(13) 0.0196(12) 0.0035(10) 0.0109(10) -0.0008(11) C2 0.0288(14) 0.0157(13) 0.0214(12) 0.0038(10) 0.0111(11) -0.0001(11) C3 0.0324(15) 0.0218(14) 0.0220(12) 0.0012(10) 0.0092(11) -0.0015(12) C4 0.0322(15) 0.0279(15) 0.0266(13) 0.0045(11) 0.0078(11) -0.0008(12) C5 0.0300(15) 0.0207(14) 0.0333(14) 0.0031(11) 0.0118(12) 0.0021(12) C6 0.0343(15) 0.0163(13) 0.0265(13) 0.0007(10) 0.0126(12) 0.0002(12) C7 0.0508(17) 0.0193(15) 0.0218(13) -0.0050(11) 0.0096(12) 0.0011(13) C8 0.0407(17) 0.0257(16) 0.0321(14) -0.0044(11) 0.0092(12) -0.0056(13) C9 0.0400(16) 0.0266(15) 0.0266(13) 0.0015(11) 0.0144(12) 0.0021(12) C10 0.0501(17) 0.0213(14) 0.0183(12) 0.0005(10) 0.0141(12) 0.0052(13) C17 0.064(4) 0.028(3) 0.040(3) -0.005(3) 0.017(3) -0.003(3) C11 0.036(5) 0.039(6) 0.027(5) -0.010(4) 0.006(3) -0.001(4) C12 0.052(8) 0.022(5) 0.041(6) -0.012(4) 0.009(6) 0.001(4) C13 0.044(6) 0.037(6) 0.027(5) -0.008(4) 0.010(4) -0.005(5) C14 0.043(5) 0.044(6) 0.031(5) -0.007(4) 0.019(4) -0.001(4) C15 0.049(4) 0.027(4) 0.051(5) -0.006(4) 0.019(4) -0.002(4) C16 0.044(5) 0.028(3) 0.040(7) -0.008(4) 0.019(5) 0.002(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 N1 1.427(3) . ? B1 N2 1.431(3) . ? B1 B1 1.611(6) 7_557 ? B2 N3 1.402(3) . ? B2 N1 1.500(3) . ? B2 B3 1.757(4) 7_557 ? B3 N4 1.402(3) . ? B3 N2 1.495(3) . ? B3 B2 1.757(4) 7_557 ? N1 C2 1.413(3) . ? N2 C1 1.402(3) . ? N3 C8 1.455(3) . ? N3 C7 1.467(3) . ? N4 C9 1.452(3) . ? N4 C10 1.458(3) . ? C1 C6 1.385(3) . ? C1 C2 1.434(3) . ? C2 C3 1.380(3) . ? C3 C4 1.384(4) . ? C3 H3 0.9500 . ? C4 C5 1.389(4) . ? C4 H4 0.9500 . ? C5 C6 1.383(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C17 C11 1.511(9) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C12 H12 0.9500 . ? C13 C14 1.3900 . ? C13 H13 0.9500 . ? C14 C15 1.3900 . ? C14 H14 0.9500 . ? C15 C16 1.3900 . ? C15 H15 0.9500 . ? C16 H16 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 111.1(2) . . ? N1 B1 B1 125.9(3) . 7_557 ? N2 B1 B1 123.0(3) . 7_557 ? N3 B2 N1 121.9(2) . . ? N3 B2 B3 123.7(2) . 7_557 ? N1 B2 B3 114.0(2) . 7_557 ? N4 B3 N2 120.8(2) . . ? N4 B3 B2 123.8(2) . 7_557 ? N2 B3 B2 114.78(19) . 7_557 ? C2 N1 B1 105.14(18) . . ? C2 N1 B2 141.8(2) . . ? B1 N1 B2 111.2(2) . . ? C1 N2 B1 105.40(18) . . ? C1 N2 B3 140.7(2) . . ? B1 N2 B3 112.7(2) . . ? B2 N3 C8 125.8(2) . . ? B2 N3 C7 122.8(2) . . ? C8 N3 C7 111.2(2) . . ? B3 N4 C9 124.8(2) . . ? B3 N4 C10 123.3(2) . . ? C9 N4 C10 111.61(18) . . ? C6 C1 N2 130.2(2) . . ? C6 C1 C2 120.3(2) . . ? N2 C1 C2 109.3(2) . . ? C3 C2 N1 131.1(2) . . ? C3 C2 C1 119.7(2) . . ? N1 C2 C1 109.0(2) . . ? C2 C3 C4 119.2(2) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 121.1(2) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 121.0(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 118.8(2) . . ? C5 C6 H6 120.6 . . ? C1 C6 H6 120.6 . . ? N3 C7 H7A 109.5 . . ? N3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N4 C9 H9A 109.5 . . ? N4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N4 C10 H10A 109.5 . . ? N4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 120.0 . . ? C12 C11 C17 119.5(6) . . ? C16 C11 C17 120.5(6) . . ? C13 C12 C11 120.0 . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.0 . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 120.0 . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C16 C15 C14 120.0 . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 120.0 . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? 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 C2 3.8(2) . . . . ? B1 B1 N1 C2 -179.2(3) 7_557 . . . ? N2 B1 N1 B2 -164.47(19) . . . . ? B1 B1 N1 B2 12.5(4) 7_557 . . . ? N3 B2 N1 C2 -24.9(4) . . . . ? B3 B2 N1 C2 161.8(2) 7_557 . . . ? N3 B2 N1 B1 136.6(2) . . . . ? B3 B2 N1 B1 -36.7(2) 7_557 . . . ? N1 B1 N2 C1 -3.6(2) . . . . ? B1 B1 N2 C1 179.3(3) 7_557 . . . ? N1 B1 N2 B3 166.77(19) . . . . ? B1 B1 N2 B3 -10.3(4) 7_557 . . . ? N4 B3 N2 C1 29.1(4) . . . . ? B2 B3 N2 C1 -159.7(3) 7_557 . . . ? N4 B3 N2 B1 -136.2(2) . . . . ? B2 B3 N2 B1 35.0(3) 7_557 . . . ? N1 B2 N3 C8 -1.5(3) . . . . ? B3 B2 N3 C8 171.1(2) 7_557 . . . ? N1 B2 N3 C7 -176.2(2) . . . . ? B3 B2 N3 C7 -3.5(3) 7_557 . . . ? N2 B3 N4 C9 9.3(3) . . . . ? B2 B3 N4 C9 -161.1(2) 7_557 . . . ? N2 B3 N4 C10 -177.5(2) . . . . ? B2 B3 N4 C10 12.1(3) 7_557 . . . ? B1 N2 C1 C6 -171.7(2) . . . . ? B3 N2 C1 C6 22.4(4) . . . . ? B1 N2 C1 C2 2.0(2) . . . . ? B3 N2 C1 C2 -164.0(3) . . . . ? B1 N1 C2 C3 171.3(2) . . . . ? B2 N1 C2 C3 -26.6(4) . . . . ? B1 N1 C2 C1 -2.5(2) . . . . ? B2 N1 C2 C1 159.7(3) . . . . ? C6 C1 C2 C3 0.1(3) . . . . ? N2 C1 C2 C3 -174.3(2) . . . . ? C6 C1 C2 N1 174.7(2) . . . . ? N2 C1 C2 N1 0.3(2) . . . . ? N1 C2 C3 C4 -173.8(2) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C2 C3 C4 C5 0.6(4) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C4 C5 C6 C1 -0.4(4) . . . . ? N2 C1 C6 C5 173.4(2) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? C16 C11 C12 C13 0.0 . . . . ? C17 C11 C12 C13 179.2(6) . . . . ? C11 C12 C13 C14 0.0 . . . . ? C12 C13 C14 C15 0.0 . . . . ? C13 C14 C15 C16 0.0 . . . . ? C14 C15 C16 C11 0.0 . . . . ? C12 C11 C16 C15 0.0 . . . . ? C17 C11 C16 C15 -179.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 58.97 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.200 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.050 data_5 _database_code_depnum_ccdc_archive 'CCDC 807913' #TrackingRef '- Combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H36 B6 N8, 2(C7 H8)' _chemical_formula_sum 'C42 H52 B6 N8' _chemical_formula_weight 733.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.4491(4) _cell_length_b 9.6202(3) _cell_length_c 31.1212(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4026.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 18947 _cell_measurement_theta_min 2.839 _cell_measurement_theta_max 64.7095 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 0.541 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6641 _exptl_absorpt_correction_T_max 0.7526 _exptl_absorpt_process_details 'SADABS-2008/1 - Bruker AXS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source Microstar_rotating_anode _diffrn_radiation_monochromator optics _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 31266 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 65.10 _reflns_number_total 3402 _reflns_number_gt 3170 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Proteum_2, BRUKER' _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELX _computing_publication_material SHELX _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+2.9795P] 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 3402 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1161 _refine_ls_wR_factor_gt 0.1142 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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 1.01096(13) 0.98074(19) 0.47331(6) 0.0231(4) Uani 1 1 d . . . B2 B 1.10611(14) 1.1984(2) 0.46936(6) 0.0277(4) Uani 1 1 d . . . B3 B 0.86916(15) 0.81868(19) 0.47699(6) 0.0269(4) Uani 1 1 d . . . N1 N 0.95675(10) 0.87160(14) 0.45211(4) 0.0239(3) Uani 1 1 d . . . N2 N 1.08062(10) 1.06140(14) 0.44883(4) 0.0242(3) Uani 1 1 d . . . N3 N 1.09656(11) 1.32378(15) 0.44738(5) 0.0301(3) Uani 1 1 d . . . N4 N 0.77464(10) 0.80500(15) 0.45848(5) 0.0296(3) Uani 1 1 d . . . C1 C 0.98572(12) 0.82590(17) 0.41098(5) 0.0232(4) Uani 1 1 d . . . C2 C 1.06590(11) 0.89613(17) 0.38976(5) 0.0228(4) Uani 1 1 d . . . C3 C 1.11250(12) 1.01579(17) 0.40821(5) 0.0236(4) Uani 1 1 d . . . C4 C 1.19086(12) 1.07862(18) 0.38678(5) 0.0270(4) Uani 1 1 d . . . H4 H 1.2221 1.1579 0.3990 0.032 Uiso 1 1 calc R . . C5 C 1.22443(12) 1.02652(19) 0.34735(5) 0.0293(4) Uani 1 1 d . . . H5 H 1.2785 1.0708 0.3332 0.035 Uiso 1 1 calc R . . C6 C 1.18071(12) 0.91293(18) 0.32879(5) 0.0272(4) Uani 1 1 d . . . H6 H 1.2049 0.8790 0.3021 0.033 Uiso 1 1 calc R . . C7 C 1.09958(12) 0.84563(17) 0.34915(5) 0.0242(4) Uani 1 1 d . . . C8 C 1.05148(12) 0.73009(17) 0.33020(5) 0.0256(4) Uani 1 1 d . . . H8 H 1.0720 0.6980 0.3027 0.031 Uiso 1 1 calc R . . C9 C 0.97578(12) 0.66455(17) 0.35122(5) 0.0268(4) Uani 1 1 d . . . H9 H 0.9445 0.5864 0.3383 0.032 Uiso 1 1 calc R . . C10 C 0.94347(12) 0.71090(17) 0.39164(5) 0.0257(4) Uani 1 1 d . . . H10 H 0.8916 0.6624 0.4059 0.031 Uiso 1 1 calc R . . C11 C 1.12152(15) 1.45671(19) 0.46723(6) 0.0369(4) Uani 1 1 d . . . H11A H 1.1383 1.4419 0.4975 0.055 Uiso 1 1 calc R . . H11B H 1.0644 1.5197 0.4652 0.055 Uiso 1 1 calc R . . H11C H 1.1786 1.4978 0.4523 0.055 Uiso 1 1 calc R . . C12 C 1.05624(15) 1.3402(2) 0.40411(6) 0.0355(4) Uani 1 1 d . . . H12A H 1.1101 1.3636 0.3842 0.053 Uiso 1 1 calc R . . H12B H 1.0067 1.4148 0.4041 0.053 Uiso 1 1 calc R . . H12C H 1.0248 1.2530 0.3950 0.053 Uiso 1 1 calc R . . C13 C 0.69214(13) 0.7374(2) 0.48080(6) 0.0359(4) Uani 1 1 d . . . H13A H 0.7104 0.7215 0.5109 0.054 Uiso 1 1 calc R . . H13B H 0.6775 0.6482 0.4670 0.054 Uiso 1 1 calc R . . H13C H 0.6332 0.7972 0.4795 0.054 Uiso 1 1 calc R . . C14 C 0.74524(14) 0.8575(2) 0.41655(6) 0.0364(4) Uani 1 1 d . . . H14A H 0.7995 0.9128 0.4044 0.055 Uiso 1 1 calc R . . H14B H 0.6859 0.9158 0.4196 0.055 Uiso 1 1 calc R . . H14C H 0.7304 0.7792 0.3974 0.055 Uiso 1 1 calc R . . C15 C 0.03642(14) 0.77647(19) 0.20829(6) 0.0334(4) Uani 1 1 d . . . C16 C 0.02861(14) 0.64560(19) 0.19025(6) 0.0340(4) Uani 1 1 d . . . H16 H -0.0354 0.6052 0.1868 0.041 Uiso 1 1 calc R . . C17 C 0.11110(14) 0.5721(2) 0.17709(6) 0.0377(4) Uani 1 1 d . . . H17 H 0.1035 0.4822 0.1649 0.045 Uiso 1 1 calc R . . C18 C 0.20439(15) 0.6288(2) 0.18160(7) 0.0428(5) Uani 1 1 d . . . H18 H 0.2614 0.5784 0.1725 0.051 Uiso 1 1 calc R . . C19 C 0.21440(15) 0.7589(2) 0.19934(7) 0.0477(6) Uani 1 1 d . . . H19 H 0.2787 0.7986 0.2025 0.057 Uiso 1 1 calc R . . C20 C 0.13118(17) 0.8327(2) 0.21272(6) 0.0421(5) Uani 1 1 d . . . H20 H 0.1391 0.9224 0.2250 0.051 Uiso 1 1 calc R . . C21 C -0.05433(18) 0.8540(2) 0.22263(7) 0.0500(6) Uani 1 1 d . . . H21A H -0.0821 0.9057 0.1983 0.075 Uiso 1 1 calc R . . H21B H -0.0363 0.9191 0.2456 0.075 Uiso 1 1 calc R . . H21C H -0.1039 0.7880 0.2334 0.075 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 0.0206(9) 0.0217(9) 0.0272(10) 0.0028(7) -0.0015(7) 0.0010(7) B2 0.0223(9) 0.0291(10) 0.0316(10) -0.0001(8) 0.0049(8) -0.0038(8) B3 0.0288(10) 0.0204(9) 0.0317(10) -0.0020(8) 0.0025(8) -0.0030(8) N1 0.0254(7) 0.0227(7) 0.0235(7) 0.0011(5) 0.0011(5) -0.0023(6) N2 0.0229(7) 0.0266(7) 0.0230(7) 0.0007(6) 0.0005(5) -0.0032(6) N3 0.0331(8) 0.0271(8) 0.0301(8) 0.0005(6) 0.0036(6) -0.0035(6) N4 0.0265(8) 0.0316(8) 0.0308(7) -0.0025(6) 0.0023(6) -0.0038(6) C1 0.0217(8) 0.0230(8) 0.0249(8) 0.0022(6) -0.0017(6) 0.0010(6) C2 0.0202(8) 0.0231(8) 0.0251(8) 0.0034(6) -0.0014(6) 0.0019(6) C3 0.0215(8) 0.0255(8) 0.0238(8) 0.0024(7) -0.0014(6) 0.0007(6) C4 0.0238(8) 0.0289(9) 0.0282(8) 0.0009(7) -0.0006(7) -0.0036(7) C5 0.0222(8) 0.0358(10) 0.0299(9) 0.0044(8) 0.0030(7) -0.0018(7) C6 0.0234(8) 0.0330(9) 0.0253(8) 0.0009(7) 0.0023(7) 0.0037(7) C7 0.0215(8) 0.0250(8) 0.0262(8) 0.0025(7) -0.0024(6) 0.0045(7) C8 0.0241(8) 0.0272(9) 0.0255(8) -0.0009(7) -0.0009(7) 0.0057(7) C9 0.0260(9) 0.0241(8) 0.0302(9) -0.0023(7) -0.0040(7) 0.0017(7) C10 0.0247(8) 0.0233(8) 0.0291(9) 0.0012(7) 0.0004(7) -0.0007(7) C11 0.0447(11) 0.0276(9) 0.0383(10) 0.0001(8) 0.0078(8) -0.0071(8) C12 0.0399(10) 0.0314(10) 0.0351(10) 0.0055(8) 0.0020(8) 0.0017(8) C13 0.0279(9) 0.0374(10) 0.0425(10) -0.0062(8) 0.0049(8) -0.0085(8) C14 0.0295(9) 0.0429(11) 0.0367(10) -0.0023(8) -0.0027(8) 0.0012(8) C15 0.0397(10) 0.0346(10) 0.0258(9) 0.0065(8) -0.0014(8) 0.0004(8) C16 0.0302(9) 0.0351(10) 0.0368(10) 0.0043(8) -0.0034(8) -0.0037(8) C17 0.0364(10) 0.0358(10) 0.0410(10) 0.0018(8) -0.0014(8) 0.0026(8) C18 0.0336(10) 0.0465(12) 0.0483(12) 0.0117(10) 0.0008(9) 0.0022(9) C19 0.0322(10) 0.0586(14) 0.0524(13) 0.0190(11) -0.0117(9) -0.0142(10) C20 0.0588(13) 0.0341(10) 0.0334(10) 0.0052(8) -0.0132(9) -0.0115(10) C21 0.0588(14) 0.0486(13) 0.0428(12) 0.0031(10) 0.0095(10) 0.0138(11) _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 1.435(2) . ? B1 N1 1.439(2) . ? B1 B1 1.728(4) 5_776 ? B2 N3 1.393(2) . ? B2 N2 1.504(2) . ? B2 B3 1.710(3) 5_776 ? B3 N4 1.402(2) . ? B3 N1 1.499(2) . ? B3 B2 1.710(3) 5_776 ? N1 C1 1.408(2) . ? N2 C3 1.405(2) . ? N3 C11 1.459(2) . ? N3 C12 1.460(2) . ? N4 C14 1.454(2) . ? N4 C13 1.462(2) . ? C1 C10 1.382(2) . ? C1 C2 1.434(2) . ? C2 C7 1.428(2) . ? C2 C3 1.431(2) . ? C3 C4 1.386(2) . ? C4 C5 1.400(2) . ? C4 H4 0.9500 . ? C5 C6 1.369(2) . ? C5 H5 0.9500 . ? C6 C7 1.418(2) . ? C6 H6 0.9500 . ? C7 C8 1.415(2) . ? C8 C9 1.365(2) . ? C8 H8 0.9500 . ? C9 C10 1.403(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.383(3) . ? C15 C20 1.391(3) . ? C15 C21 1.498(3) . ? C16 C17 1.378(3) . ? C16 H16 0.9500 . ? C17 C18 1.375(3) . ? C17 H17 0.9500 . ? C18 C19 1.374(3) . ? C18 H18 0.9500 . ? C19 C20 1.389(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 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 N2 B1 N1 118.82(15) . . ? N2 B1 B1 120.38(18) . 5_776 ? N1 B1 B1 120.74(18) . 5_776 ? N3 B2 N2 121.95(16) . . ? N3 B2 B3 125.49(16) . 5_776 ? N2 B2 B3 112.02(14) . 5_776 ? N4 B3 N1 122.16(16) . . ? N4 B3 B2 124.65(16) . 5_776 ? N1 B3 B2 112.59(14) . 5_776 ? C1 N1 B1 120.30(14) . . ? C1 N1 B3 125.52(14) . . ? B1 N1 B3 114.16(13) . . ? C3 N2 B1 120.52(14) . . ? C3 N2 B2 125.89(14) . . ? B1 N2 B2 113.39(13) . . ? B2 N3 C11 121.99(15) . . ? B2 N3 C12 125.50(15) . . ? C11 N3 C12 112.42(14) . . ? B3 N4 C14 125.65(15) . . ? B3 N4 C13 122.33(15) . . ? C14 N4 C13 112.00(14) . . ? C10 C1 N1 122.15(14) . . ? C10 C1 C2 119.07(15) . . ? N1 C1 C2 118.66(14) . . ? C7 C2 C3 119.34(14) . . ? C7 C2 C1 119.08(15) . . ? C3 C2 C1 121.58(15) . . ? C4 C3 N2 121.92(15) . . ? C4 C3 C2 119.40(15) . . ? N2 C3 C2 118.59(14) . . ? C3 C4 C5 120.71(16) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 121.14(16) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 120.42(15) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 121.61(15) . . ? C8 C7 C2 119.42(15) . . ? C6 C7 C2 118.96(15) . . ? C9 C8 C7 120.28(15) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 120.93(16) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C1 C10 C9 121.17(15) . . ? C1 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? N3 C11 H11A 109.5 . . ? N3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N4 C13 H13A 109.5 . . ? N4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N4 C14 H14A 109.5 . . ? N4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 117.63(18) . . ? C16 C15 C21 120.83(18) . . ? C20 C15 C21 121.55(19) . . ? C17 C16 C15 121.79(18) . . ? C17 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? C18 C17 C16 120.07(19) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C19 C18 C17 119.4(2) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C20 120.44(19) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C19 C20 C15 120.65(19) . . ? C19 C20 H20 119.7 . . ? C15 C20 H20 119.7 . . ? C15 C21 H21A 109.5 . . ? C15 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C15 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? 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 12.9(2) . . . . ? B1 B1 N1 C1 -169.78(17) 5_776 . . . ? N2 B1 N1 B3 -165.39(15) . . . . ? B1 B1 N1 B3 11.9(3) 5_776 . . . ? N4 B3 N1 C1 -48.0(2) . . . . ? B2 B3 N1 C1 140.55(15) 5_776 . . . ? N4 B3 N1 B1 130.22(17) . . . . ? B2 B3 N1 B1 -41.23(19) 5_776 . . . ? N1 B1 N2 C3 -14.5(2) . . . . ? B1 B1 N2 C3 168.19(17) 5_776 . . . ? N1 B1 N2 B2 160.59(15) . . . . ? B1 B1 N2 B2 -16.7(2) 5_776 . . . ? N3 B2 N2 C3 48.7(2) . . . . ? B3 B2 N2 C3 -139.28(15) 5_776 . . . ? N3 B2 N2 B1 -126.08(17) . . . . ? B3 B2 N2 B1 45.93(19) 5_776 . . . ? N2 B2 N3 C11 -179.84(16) . . . . ? B3 B2 N3 C11 9.3(3) 5_776 . . . ? N2 B2 N3 C12 4.0(3) . . . . ? B3 B2 N3 C12 -166.93(16) 5_776 . . . ? N1 B3 N4 C14 -9.7(3) . . . . ? B2 B3 N4 C14 160.71(17) 5_776 . . . ? N1 B3 N4 C13 172.12(15) . . . . ? B2 B3 N4 C13 -17.5(3) 5_776 . . . ? B1 N1 C1 C10 172.18(15) . . . . ? B3 N1 C1 C10 -9.7(2) . . . . ? B1 N1 C1 C2 -3.9(2) . . . . ? B3 N1 C1 C2 174.21(15) . . . . ? C10 C1 C2 C7 0.2(2) . . . . ? N1 C1 C2 C7 176.46(14) . . . . ? C10 C1 C2 C3 179.94(15) . . . . ? N1 C1 C2 C3 -3.9(2) . . . . ? B1 N2 C3 C4 -169.52(15) . . . . ? B2 N2 C3 C4 16.0(2) . . . . ? B1 N2 C3 C2 6.9(2) . . . . ? B2 N2 C3 C2 -167.52(15) . . . . ? C7 C2 C3 C4 -1.4(2) . . . . ? C1 C2 C3 C4 178.90(15) . . . . ? C7 C2 C3 N2 -177.96(14) . . . . ? C1 C2 C3 N2 2.4(2) . . . . ? N2 C3 C4 C5 176.65(15) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C4 C5 C6 C7 0.3(3) . . . . ? C5 C6 C7 C8 178.47(15) . . . . ? C5 C6 C7 C2 -1.5(2) . . . . ? C3 C2 C7 C8 -177.95(14) . . . . ? C1 C2 C7 C8 1.7(2) . . . . ? C3 C2 C7 C6 2.0(2) . . . . ? C1 C2 C7 C6 -178.26(14) . . . . ? C6 C7 C8 C9 177.78(15) . . . . ? C2 C7 C8 C9 -2.2(2) . . . . ? C7 C8 C9 C10 0.7(2) . . . . ? N1 C1 C10 C9 -177.89(15) . . . . ? C2 C1 C10 C9 -1.8(2) . . . . ? C8 C9 C10 C1 1.4(2) . . . . ? C20 C15 C16 C17 0.2(3) . . . . ? C21 C15 C16 C17 -179.60(18) . . . . ? C15 C16 C17 C18 -0.2(3) . . . . ? C16 C17 C18 C19 0.1(3) . . . . ? C17 C18 C19 C20 0.1(3) . . . . ? C18 C19 C20 C15 -0.2(3) . . . . ? C16 C15 C20 C19 0.0(3) . . . . ? C21 C15 C20 C19 179.79(18) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 65.10 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.358 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.041 data_4 _database_code_depnum_ccdc_archive 'CCDC 807914' #TrackingRef '- Combined.cif' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C20 H16 B2 N4, 2(C3 H7 N O)' _chemical_formula_sum 'C26 H30 B2 N6 O2' _chemical_formula_weight 480.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 12.8216(7) _cell_length_b 13.9708(8) _cell_length_c 14.5010(8) _cell_angle_alpha 90.00 _cell_angle_beta 104.001(3) _cell_angle_gamma 90.00 _cell_volume 2520.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5398 _cell_measurement_theta_min 3.242 _cell_measurement_theta_max 29.363 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.777 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.366 _diffrn_detector_type 'Bruker-AXS SMART APEX' _diffrn_measurement_details 'frames, 0.3\% width' _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Bruker-AXS Kappa' _diffrn_measurement_method '\w & \f scans' _diffrn_measurement_specimen_support ; glass fibre ; _diffrn_radiation_collimation '0.5 mm double pinhole' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe X-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71074 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 40 _diffrn_source_power 2 _diffrn_source_size '0.4 x 8 mm fine focus' _diffrn_source_target Mo _diffrn_source_type 'Bruker-AXS KFF Mo 2K 90\% Ceramic' _diffrn_source_voltage 50 _diffrn_reflns_number 33967 _diffrn_reflns_av_R_equivalents 0.0741 _diffrn_reflns_av_sigmaI/netI 0.0613 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 29.57 _reflns_number_total 7023 _reflns_number_gt 4239 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex II (Bruker-AXS, 2007)' _computing_cell_refinement 'Apex II (Bruker-AXS, 2007)' _computing_data_reduction ; SAINT v7.34A (Bruker-AXS, 2007) & XPREP v2005/4 (Bruker-AXS, 2005) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1356P)^2^+0.0414P] 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 7023 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1112 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.2216 _refine_ls_wR_factor_gt 0.1655 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.46965(19) 0.04615(16) 0.52077(18) 0.0270(5) Uani 1 1 d . . . N1 N 0.39366(14) 0.10652(12) 0.46024(12) 0.0279(4) Uani 1 1 d . . . H1 H 0.3760 0.0934 0.3991 0.033 Uiso 1 1 calc R . . N2 N 0.49186(13) 0.06916(11) 0.61908(12) 0.0265(4) Uani 1 1 d . . . H2A H 0.5378 0.0329 0.6591 0.032 Uiso 1 1 calc R . . C1 C 0.34526(16) 0.18550(14) 0.49183(15) 0.0270(4) Uani 1 1 d . . . C2 C 0.27429(18) 0.24466(15) 0.43024(16) 0.0327(5) Uani 1 1 d . . . H2 H 0.2557 0.2312 0.3641 0.039 Uiso 1 1 calc R . . C3 C 0.22962(19) 0.32459(16) 0.46545(17) 0.0377(5) Uani 1 1 d . . . H3 H 0.1820 0.3654 0.4224 0.045 Uiso 1 1 calc R . . C4 C 0.25335(18) 0.34463(16) 0.56028(17) 0.0352(5) Uani 1 1 d . . . H4 H 0.2229 0.3995 0.5824 0.042 Uiso 1 1 calc R . . C5 C 0.32312(17) 0.28433(14) 0.62621(15) 0.0288(4) Uani 1 1 d . . . C6 C 0.34785(17) 0.30075(15) 0.72571(16) 0.0318(5) Uani 1 1 d . . . H6 H 0.3149 0.3525 0.7504 0.038 Uiso 1 1 calc R . . C7 C 0.41891(18) 0.24251(15) 0.78666(16) 0.0322(5) Uani 1 1 d . . . H7 H 0.4346 0.2545 0.8531 0.039 Uiso 1 1 calc R . . C8 C 0.46888(17) 0.16536(15) 0.75229(15) 0.0290(5) Uani 1 1 d . . . H8 H 0.5190 0.1266 0.7953 0.035 Uiso 1 1 calc R . . C9 C 0.44526(15) 0.14573(13) 0.65593(15) 0.0245(4) Uani 1 1 d . . . C10 C 0.37137(15) 0.20476(13) 0.59126(15) 0.0249(4) Uani 1 1 d . . . B2 B 0.47412(18) 0.04542(14) 0.02668(16) 0.0218(4) Uani 1 1 d . . . N3 N 0.38307(13) 0.09918(10) -0.02200(11) 0.0229(4) Uani 1 1 d . . . H3A H 0.3529 0.0839 -0.0813 0.027 Uiso 1 1 calc R . . N4 N 0.51768(13) 0.07297(11) 0.12232(11) 0.0226(4) Uani 1 1 d . . . H4A H 0.5720 0.0396 0.1558 0.027 Uiso 1 1 calc R . . C11 C 0.33908(15) 0.17428(12) 0.01852(13) 0.0217(4) Uani 1 1 d . . . C12 C 0.24908(16) 0.22343(14) -0.03021(14) 0.0265(4) Uani 1 1 d . . . H12 H 0.2165 0.2070 -0.0943 0.032 Uiso 1 1 calc R . . C13 C 0.20535(17) 0.29746(14) 0.01422(15) 0.0288(5) Uani 1 1 d . . . H13 H 0.1425 0.3295 -0.0200 0.035 Uiso 1 1 calc R . . C14 C 0.25154(16) 0.32438(14) 0.10579(14) 0.0264(4) Uani 1 1 d . . . H14 H 0.2209 0.3748 0.1345 0.032 Uiso 1 1 calc R . . C15 C 0.34504(15) 0.27695(13) 0.15770(14) 0.0222(4) Uani 1 1 d . . . C16 C 0.39633(16) 0.30256(13) 0.25208(14) 0.0262(4) Uani 1 1 d . . . H16 H 0.3692 0.3543 0.2819 0.031 Uiso 1 1 calc R . . C17 C 0.48478(17) 0.25332(14) 0.30073(14) 0.0273(4) Uani 1 1 d . . . H17 H 0.5181 0.2712 0.3642 0.033 Uiso 1 1 calc R . . C18 C 0.52720(16) 0.17699(14) 0.25883(14) 0.0255(4) Uani 1 1 d . . . H18 H 0.5889 0.1440 0.2940 0.031 Uiso 1 1 calc R . . C19 C 0.47987(15) 0.14949(13) 0.16672(13) 0.0213(4) Uani 1 1 d . . . C20 C 0.38824(14) 0.20021(12) 0.11390(13) 0.0198(4) Uani 1 1 d . . . O1 O 0.27150(12) 0.03039(10) 0.78311(10) 0.0305(4) Uani 1 1 d . . . C21 C 0.20445(17) 0.08081(14) 0.72904(15) 0.0273(4) Uani 1 1 d . . . H21 H 0.1778 0.1348 0.7560 0.033 Uiso 1 1 calc R . . N5 N 0.16628(14) 0.06637(12) 0.63667(12) 0.0270(4) Uani 1 1 d . . . C22 C 0.20626(18) -0.01149(15) 0.58808(16) 0.0324(5) Uani 1 1 d . . . H22A H 0.2723 -0.0373 0.6294 0.049 Uiso 1 1 calc R . . H22B H 0.2215 0.0126 0.5292 0.049 Uiso 1 1 calc R . . H22C H 0.1519 -0.0621 0.5729 0.049 Uiso 1 1 calc R . . C23 C 0.0867(2) 0.13006(17) 0.57952(17) 0.0400(6) Uani 1 1 d . . . H23A H 0.0668 0.1792 0.6204 0.060 Uiso 1 1 calc R . . H23B H 0.0228 0.0932 0.5486 0.060 Uiso 1 1 calc R . . H23C H 0.1169 0.1608 0.5310 0.060 Uiso 1 1 calc R . . O2 O 0.18915(13) 0.51930(11) 0.23667(12) 0.0377(4) Uani 1 1 d . . . C24 C 0.25843(19) 0.53870(15) 0.30757(17) 0.0352(5) Uani 1 1 d . . . H24 H 0.2391 0.5382 0.3668 0.042 Uiso 1 1 calc R . . N6 N 0.36043(17) 0.56080(14) 0.30772(18) 0.0505(6) Uani 1 1 d . . . C25 C 0.4354(3) 0.5896(3) 0.3940(3) 0.1098(18) Uani 1 1 d . . . H25A H 0.4513 0.6580 0.3907 0.165 Uiso 1 1 calc R . . H25B H 0.5020 0.5527 0.4019 0.165 Uiso 1 1 calc R . . H25C H 0.4041 0.5778 0.4483 0.165 Uiso 1 1 calc R . . C26 C 0.3968(2) 0.5591(2) 0.2205(3) 0.0668(9) Uani 1 1 d . . . H26A H 0.3391 0.5349 0.1685 0.100 Uiso 1 1 calc R . . H26B H 0.4597 0.5172 0.2286 0.100 Uiso 1 1 calc R . . H26C H 0.4163 0.6240 0.2053 0.100 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 0.0245(11) 0.0204(10) 0.0366(13) 0.0023(9) 0.0086(10) -0.0003(8) N1 0.0315(9) 0.0227(8) 0.0295(9) -0.0005(7) 0.0074(7) 0.0053(7) N2 0.0260(9) 0.0183(8) 0.0339(10) 0.0043(7) 0.0045(7) 0.0041(6) C1 0.0270(10) 0.0212(9) 0.0329(11) 0.0028(8) 0.0074(9) 0.0041(8) C2 0.0359(12) 0.0291(11) 0.0316(12) 0.0023(9) 0.0052(10) 0.0074(9) C3 0.0385(13) 0.0296(11) 0.0426(14) 0.0055(10) 0.0052(10) 0.0120(9) C4 0.0352(12) 0.0254(10) 0.0440(14) -0.0003(9) 0.0077(10) 0.0099(9) C5 0.0296(11) 0.0228(10) 0.0344(12) -0.0006(8) 0.0085(9) 0.0021(8) C6 0.0357(12) 0.0232(10) 0.0384(12) -0.0067(9) 0.0125(10) -0.0018(8) C7 0.0384(12) 0.0260(10) 0.0323(12) -0.0032(8) 0.0086(10) -0.0051(9) C8 0.0298(11) 0.0233(10) 0.0323(12) 0.0011(8) 0.0043(9) -0.0034(8) C9 0.0230(10) 0.0183(9) 0.0317(11) 0.0014(8) 0.0055(8) -0.0007(7) C10 0.0241(10) 0.0186(9) 0.0319(11) 0.0005(8) 0.0065(8) 0.0007(7) B2 0.0238(11) 0.0141(9) 0.0264(11) 0.0012(8) 0.0041(9) -0.0007(7) N3 0.0277(9) 0.0155(7) 0.0226(8) -0.0031(6) 0.0004(7) 0.0021(6) N4 0.0244(8) 0.0156(7) 0.0254(8) 0.0010(6) 0.0012(7) 0.0043(6) C11 0.0251(10) 0.0140(8) 0.0246(10) -0.0011(7) 0.0033(8) -0.0005(7) C12 0.0287(10) 0.0229(9) 0.0245(10) -0.0021(8) -0.0005(8) 0.0038(8) C13 0.0294(11) 0.0240(10) 0.0296(11) -0.0003(8) 0.0007(8) 0.0080(8) C14 0.0278(10) 0.0189(9) 0.0309(11) -0.0028(8) 0.0039(9) 0.0049(7) C15 0.0262(10) 0.0150(8) 0.0249(10) -0.0005(7) 0.0052(8) 0.0000(7) C16 0.0313(11) 0.0179(9) 0.0281(10) -0.0041(8) 0.0046(8) 0.0002(8) C17 0.0329(11) 0.0235(10) 0.0222(10) -0.0040(7) 0.0004(8) -0.0010(8) C18 0.0266(10) 0.0213(9) 0.0256(10) -0.0017(8) 0.0001(8) 0.0020(7) C19 0.0236(9) 0.0150(8) 0.0245(10) -0.0006(7) 0.0045(8) -0.0006(7) C20 0.0221(9) 0.0122(8) 0.0236(9) 0.0008(7) 0.0027(7) -0.0015(6) O1 0.0345(8) 0.0232(7) 0.0284(8) 0.0020(6) -0.0032(6) -0.0019(6) C21 0.0306(11) 0.0201(9) 0.0292(11) -0.0024(8) 0.0032(9) -0.0033(8) N5 0.0266(9) 0.0235(8) 0.0275(9) -0.0004(7) 0.0001(7) 0.0036(7) C22 0.0374(12) 0.0249(10) 0.0321(11) -0.0033(9) 0.0027(9) 0.0053(9) C23 0.0412(13) 0.0342(12) 0.0372(13) 0.0014(10) -0.0048(10) 0.0135(10) O2 0.0337(9) 0.0369(9) 0.0402(9) -0.0081(7) 0.0042(7) -0.0071(7) C24 0.0394(13) 0.0216(10) 0.0417(13) -0.0079(9) 0.0039(11) 0.0075(9) N6 0.0348(11) 0.0298(10) 0.0758(17) -0.0149(11) -0.0080(11) 0.0026(9) C25 0.051(2) 0.108(3) 0.142(4) -0.064(3) -0.032(2) 0.007(2) C26 0.0472(17) 0.0454(16) 0.114(3) 0.0197(17) 0.0316(18) -0.0015(13) _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 1.420(3) . ? B1 N2 1.421(3) . ? B1 B1 1.690(5) 3_656 ? N1 C1 1.396(2) . ? N1 H1 0.8800 . ? N2 C9 1.393(2) . ? N2 H2A 0.8800 . ? C1 C2 1.384(3) . ? C1 C10 1.425(3) . ? C2 C3 1.406(3) . ? C2 H2 0.9500 . ? C3 C4 1.364(3) . ? C3 H3 0.9500 . ? C4 C5 1.418(3) . ? C4 H4 0.9500 . ? C5 C6 1.419(3) . ? C5 C10 1.424(3) . ? C6 C7 1.372(3) . ? C6 H6 0.9500 . ? C7 C8 1.405(3) . ? C7 H7 0.9500 . ? C8 C9 1.384(3) . ? C8 H8 0.9500 . ? C9 C10 1.424(3) . ? B2 N4 1.417(3) . ? B2 N3 1.423(3) . ? B2 B2 1.702(4) 3_655 ? N3 C11 1.387(2) . ? N3 H3A 0.8800 . ? N4 C19 1.394(2) . ? N4 H4A 0.8800 . ? C11 C12 1.381(3) . ? C11 C20 1.421(3) . ? C12 C13 1.405(3) . ? C12 H12 0.9500 . ? C13 C14 1.369(3) . ? C13 H13 0.9500 . ? C14 C15 1.416(3) . ? C14 H14 0.9500 . ? C15 C16 1.414(3) . ? C15 C20 1.425(2) . ? C16 C17 1.368(3) . ? C16 H16 0.9500 . ? C17 C18 1.401(3) . ? C17 H17 0.9500 . ? C18 C19 1.381(3) . ? C18 H18 0.9500 . ? C19 C20 1.426(2) . ? O1 C21 1.234(2) . ? C21 N5 1.326(3) . ? C21 H21 0.9500 . ? N5 C23 1.453(3) . ? N5 C22 1.455(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? O2 C24 1.216(3) . ? C24 N6 1.343(3) . ? C24 H24 0.9500 . ? N6 C25 1.439(4) . ? N6 C26 1.451(4) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 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 N1 B1 N2 115.24(18) . . ? N1 B1 B1 122.6(3) . 3_656 ? N2 B1 B1 122.1(2) . 3_656 ? C1 N1 B1 124.02(18) . . ? C1 N1 H1 118.0 . . ? B1 N1 H1 118.0 . . ? C9 N2 B1 123.90(17) . . ? C9 N2 H2A 118.0 . . ? B1 N2 H2A 118.0 . . ? C2 C1 N1 122.35(19) . . ? C2 C1 C10 119.81(18) . . ? N1 C1 C10 117.84(17) . . ? C1 C2 C3 120.1(2) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 121.2(2) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 120.6(2) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 122.61(19) . . ? C4 C5 C10 118.78(19) . . ? C6 C5 C10 118.60(19) . . ? C7 C6 C5 120.6(2) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 121.0(2) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C9 C8 C7 120.2(2) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 N2 122.00(18) . . ? C8 C9 C10 119.91(18) . . ? N2 C9 C10 118.09(18) . . ? C9 C10 C5 119.66(19) . . ? C9 C10 C1 120.88(18) . . ? C5 C10 C1 119.46(18) . . ? N4 B2 N3 115.07(17) . . ? N4 B2 B2 122.9(2) . 3_655 ? N3 B2 B2 122.1(2) . 3_655 ? C11 N3 B2 123.90(16) . . ? C11 N3 H3A 118.1 . . ? B2 N3 H3A 118.1 . . ? C19 N4 B2 124.16(16) . . ? C19 N4 H4A 117.9 . . ? B2 N4 H4A 117.9 . . ? C12 C11 N3 122.29(17) . . ? C12 C11 C20 119.35(17) . . ? N3 C11 C20 118.35(16) . . ? C11 C12 C13 120.53(18) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 121.33(18) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C15 119.92(18) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 122.13(17) . . ? C16 C15 C20 118.82(17) . . ? C14 C15 C20 119.05(17) . . ? C17 C16 C15 120.37(18) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 121.32(18) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C19 C18 C17 120.35(18) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 N4 122.64(17) . . ? C18 C19 C20 119.56(17) . . ? N4 C19 C20 117.80(16) . . ? C11 C20 C15 119.79(16) . . ? C11 C20 C19 120.65(16) . . ? C15 C20 C19 119.55(17) . . ? O1 C21 N5 125.80(19) . . ? O1 C21 H21 117.1 . . ? N5 C21 H21 117.1 . . ? C21 N5 C23 121.31(18) . . ? C21 N5 C22 121.06(17) . . ? C23 N5 C22 117.57(17) . . ? N5 C22 H22A 109.5 . . ? N5 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N5 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N5 C23 H23A 109.5 . . ? N5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O2 C24 N6 124.4(2) . . ? O2 C24 H24 117.8 . . ? N6 C24 H24 117.8 . . ? C24 N6 C25 120.7(3) . . ? C24 N6 C26 120.9(2) . . ? C25 N6 C26 118.3(3) . . ? N6 C25 H25A 109.5 . . ? N6 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N6 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N6 C26 H26A 109.5 . . ? N6 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N6 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? 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 2.2(3) . . . . ? B1 B1 N1 C1 -177.4(2) 3_656 . . . ? N1 B1 N2 C9 -0.9(3) . . . . ? B1 B1 N2 C9 178.6(2) 3_656 . . . ? B1 N1 C1 C2 177.7(2) . . . . ? B1 N1 C1 C10 -2.0(3) . . . . ? N1 C1 C2 C3 -178.5(2) . . . . ? C10 C1 C2 C3 1.2(3) . . . . ? C1 C2 C3 C4 -1.2(4) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C3 C4 C5 C6 -178.2(2) . . . . ? C3 C4 C5 C10 2.5(3) . . . . ? C4 C5 C6 C7 -177.6(2) . . . . ? C10 C5 C6 C7 1.6(3) . . . . ? C5 C6 C7 C8 0.0(3) . . . . ? C6 C7 C8 C9 -1.3(3) . . . . ? C7 C8 C9 N2 -179.09(18) . . . . ? C7 C8 C9 C10 1.0(3) . . . . ? B1 N2 C9 C8 179.74(19) . . . . ? B1 N2 C9 C10 -0.3(3) . . . . ? C8 C9 C10 C5 0.7(3) . . . . ? N2 C9 C10 C5 -179.27(17) . . . . ? C8 C9 C10 C1 -179.55(18) . . . . ? N2 C9 C10 C1 0.5(3) . . . . ? C4 C5 C10 C9 177.31(19) . . . . ? C6 C5 C10 C9 -2.0(3) . . . . ? C4 C5 C10 C1 -2.5(3) . . . . ? C6 C5 C10 C1 178.27(18) . . . . ? C2 C1 C10 C9 -179.15(19) . . . . ? N1 C1 C10 C9 0.6(3) . . . . ? C2 C1 C10 C5 0.6(3) . . . . ? N1 C1 C10 C5 -179.63(18) . . . . ? N4 B2 N3 C11 0.9(3) . . . . ? B2 B2 N3 C11 -179.3(2) 3_655 . . . ? N3 B2 N4 C19 -3.0(3) . . . . ? B2 B2 N4 C19 177.2(2) 3_655 . . . ? B2 N3 C11 C12 -178.46(19) . . . . ? B2 N3 C11 C20 0.8(3) . . . . ? N3 C11 C12 C13 178.33(18) . . . . ? C20 C11 C12 C13 -0.9(3) . . . . ? C11 C12 C13 C14 1.4(3) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? C13 C14 C15 C16 179.43(19) . . . . ? C13 C14 C15 C20 -1.3(3) . . . . ? C14 C15 C16 C17 178.21(19) . . . . ? C20 C15 C16 C17 -1.1(3) . . . . ? C15 C16 C17 C18 0.3(3) . . . . ? C16 C17 C18 C19 -0.2(3) . . . . ? C17 C18 C19 N4 -178.80(18) . . . . ? C17 C18 C19 C20 0.9(3) . . . . ? B2 N4 C19 C18 -177.10(18) . . . . ? B2 N4 C19 C20 3.2(3) . . . . ? C12 C11 C20 C15 -0.7(3) . . . . ? N3 C11 C20 C15 -179.94(16) . . . . ? C12 C11 C20 C19 178.66(17) . . . . ? N3 C11 C20 C19 -0.6(3) . . . . ? C16 C15 C20 C11 -178.94(17) . . . . ? C14 C15 C20 C11 1.8(3) . . . . ? C16 C15 C20 C19 1.7(3) . . . . ? C14 C15 C20 C19 -177.57(17) . . . . ? C18 C19 C20 C11 179.02(17) . . . . ? N4 C19 C20 C11 -1.3(3) . . . . ? C18 C19 C20 C15 -1.6(3) . . . . ? N4 C19 C20 C15 178.04(16) . . . . ? O1 C21 N5 C23 179.6(2) . . . . ? O1 C21 N5 C22 -3.2(3) . . . . ? O2 C24 N6 C25 175.5(3) . . . . ? O2 C24 N6 C26 -2.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.651 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.129 data_6 _database_code_depnum_ccdc_archive 'CCDC 807915' #TrackingRef '- Combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H44 B6 N8' _chemical_formula_sum 'C32 H44 B6 N8' _chemical_formula_weight 605.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.9997(8) _cell_length_b 12.1731(9) _cell_length_c 14.0679(13) _cell_angle_alpha 94.107(6) _cell_angle_beta 104.802(5) _cell_angle_gamma 119.494(3) _cell_volume 1681.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4524 _cell_measurement_theta_min 4.62 _cell_measurement_theta_max 64.83 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 0.540 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4159 _exptl_absorpt_correction_T_max 0.8642 _exptl_absorpt_process_details 'SADABS V2008/1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Microstar CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5585 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 65.83 _reflns_number_total 5585 _reflns_number_gt 4832 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker PROTEUM' _computing_cell_refinement 'Bruker PROTEUM' _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. The crystal was a partial merohedral twin with two domains. Each domain was indexed independently using the Apex II software and integrated simultaneously using SAINT. The structure was solved using 'detwinned' HKLF 4 data and refined against all reflections using HKLF 5. This resulted in a domain ratio of 0.66:0.34 for the two domains. ; _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^)+(0.0843P)^2^+2.4969P] 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 5585 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0676 _refine_ls_wR_factor_ref 0.1850 _refine_ls_wR_factor_gt 0.1655 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.0516(3) 0.2768(4) 0.1988(3) 0.0190(8) Uani 1 1 d . . . B2 B -0.0107(4) 0.3041(4) 0.0284(3) 0.0173(8) Uani 1 1 d . . . B3 B 0.1377(4) 0.3040(4) 0.0632(3) 0.0196(8) Uani 1 1 d . . . B4 B 0.0534(3) 0.2770(4) 0.3215(3) 0.0194(8) Uani 1 1 d . . . B5 B -0.0060(4) 0.1922(4) 0.4635(3) 0.0193(8) Uani 1 1 d . . . B6 B 0.1449(4) 0.3394(4) 0.5008(3) 0.0188(8) Uani 1 1 d . . . N1 N -0.0374(3) 0.3031(3) 0.1251(2) 0.0191(6) Uani 1 1 d . . . N2 N 0.1393(3) 0.2563(3) 0.1567(2) 0.0200(6) Uani 1 1 d . . . N3 N -0.0873(3) 0.3136(3) -0.0610(2) 0.0211(6) Uani 1 1 d . . . N4 N 0.2547(3) 0.3682(3) 0.0356(2) 0.0211(6) Uani 1 1 d . . . N5 N -0.0362(3) 0.1639(3) 0.3531(2) 0.0179(6) Uani 1 1 d . . . N6 N 0.1482(3) 0.3873(3) 0.4068(2) 0.0177(6) Uani 1 1 d . . . N7 N -0.0830(3) 0.1090(3) 0.5169(2) 0.0219(6) Uani 1 1 d . . . N8 N 0.2612(3) 0.3914(3) 0.5869(2) 0.0217(6) Uani 1 1 d . . . C1 C -0.1485(3) 0.2990(3) 0.1471(2) 0.0187(7) Uani 1 1 d . . . C2 C -0.2823(3) 0.2026(4) 0.0901(3) 0.0245(8) Uani 1 1 d . . . H2 H -0.2995 0.1413 0.0340 0.029 Uiso 1 1 calc R . . C3 C -0.3897(4) 0.1957(4) 0.1142(3) 0.0259(8) Uani 1 1 d . . . H3 H -0.4801 0.1288 0.0753 0.031 Uiso 1 1 calc R . . C4 C -0.3669(4) 0.2853(4) 0.1948(3) 0.0286(9) Uani 1 1 d . . . H4 H -0.4411 0.2814 0.2104 0.034 Uiso 1 1 calc R . . C5 C -0.2343(4) 0.3809(4) 0.2525(3) 0.0261(8) Uani 1 1 d . . . H5 H -0.2177 0.4416 0.3087 0.031 Uiso 1 1 calc R . . C6 C -0.1261(3) 0.3884(3) 0.2288(2) 0.0214(7) Uani 1 1 d . . . H6 H -0.0359 0.4550 0.2683 0.026 Uiso 1 1 calc R . . C7 C 0.2104(3) 0.1961(3) 0.1975(3) 0.0202(7) Uani 1 1 d . . . C8 C 0.2096(3) 0.1034(3) 0.1323(3) 0.0242(8) Uani 1 1 d . . . H8 H 0.1611 0.0815 0.0621 0.029 Uiso 1 1 calc R . . C9 C 0.2780(4) 0.0427(4) 0.1682(3) 0.0305(9) Uani 1 1 d . . . H9 H 0.2766 -0.0198 0.1226 0.037 Uiso 1 1 calc R . . C10 C 0.3492(4) 0.0733(4) 0.2711(3) 0.0313(9) Uani 1 1 d . . . H10 H 0.3976 0.0330 0.2961 0.038 Uiso 1 1 calc R . . C11 C 0.3483(3) 0.1630(4) 0.3364(3) 0.0280(8) Uani 1 1 d . . . H11 H 0.3954 0.1832 0.4068 0.034 Uiso 1 1 calc R . . C12 C 0.2797(3) 0.2240(4) 0.3006(3) 0.0222(7) Uani 1 1 d . . . H12 H 0.2800 0.2852 0.3467 0.027 Uiso 1 1 calc R . . C13 C -0.1813(3) 0.3579(4) -0.0699(3) 0.0260(8) Uani 1 1 d . . . H13A H -0.2749 0.2831 -0.0974 0.039 Uiso 1 1 calc R . . H13B H -0.1664 0.4174 -0.1153 0.039 Uiso 1 1 calc R . . H13C H -0.1660 0.4032 -0.0030 0.039 Uiso 1 1 calc R . . C14 C -0.0799(4) 0.2790(4) -0.1604(3) 0.0272(8) Uani 1 1 d . . . H14A H -0.0407 0.3569 -0.1869 0.041 Uiso 1 1 calc R . . H14B H -0.1714 0.2150 -0.2071 0.041 Uiso 1 1 calc R . . H14C H -0.0226 0.2420 -0.1537 0.041 Uiso 1 1 calc R . . C15 C 0.2606(4) 0.4299(4) -0.0501(3) 0.0267(8) Uani 1 1 d . . . H15A H 0.1720 0.4186 -0.0834 0.040 Uiso 1 1 calc R . . H15B H 0.2836 0.3896 -0.0985 0.040 Uiso 1 1 calc R . . H15C H 0.3301 0.5227 -0.0259 0.040 Uiso 1 1 calc R . . C16 C 0.3897(3) 0.3982(4) 0.0942(3) 0.0255(8) Uani 1 1 d . . . H16A H 0.3886 0.3747 0.1593 0.038 Uiso 1 1 calc R . . H16B H 0.4554 0.4914 0.1059 0.038 Uiso 1 1 calc R . . H16C H 0.4157 0.3489 0.0568 0.038 Uiso 1 1 calc R . . C17 C -0.1539(3) 0.0559(3) 0.2787(2) 0.0211(7) Uani 1 1 d . . . C18 C -0.1401(4) -0.0197(4) 0.2086(3) 0.0262(8) Uani 1 1 d . . . H18 H -0.0524 -0.0006 0.2110 0.031 Uiso 1 1 calc R . . C19 C -0.2556(4) -0.1232(4) 0.1355(3) 0.0313(9) Uani 1 1 d . . . H19 H -0.2458 -0.1736 0.0873 0.038 Uiso 1 1 calc R . . C20 C -0.3834(4) -0.1541(4) 0.1315(3) 0.0332(10) Uani 1 1 d . . . H20 H -0.4616 -0.2268 0.0826 0.040 Uiso 1 1 calc R . . C21 C -0.3965(4) -0.0768(4) 0.2003(3) 0.0304(9) Uani 1 1 d . . . H21 H -0.4843 -0.0958 0.1976 0.036 Uiso 1 1 calc R . . C22 C -0.2822(3) 0.0277(4) 0.2726(3) 0.0248(8) Uani 1 1 d . . . H22 H -0.2923 0.0805 0.3185 0.030 Uiso 1 1 calc R . . C23 C 0.2278(3) 0.5187(3) 0.4001(2) 0.0203(7) Uani 1 1 d . . . C24 C 0.3007(3) 0.5525(3) 0.3339(3) 0.0224(7) Uani 1 1 d . . . H24 H 0.2966 0.4872 0.2893 0.027 Uiso 1 1 calc R . . C25 C 0.3805(4) 0.6835(4) 0.3331(3) 0.0293(9) Uani 1 1 d . . . H25 H 0.4295 0.7063 0.2869 0.035 Uiso 1 1 calc R . . C26 C 0.3891(4) 0.7794(4) 0.3979(3) 0.0330(9) Uani 1 1 d . . . H26 H 0.4463 0.8681 0.3986 0.040 Uiso 1 1 calc R . . C27 C 0.3136(4) 0.7454(4) 0.4622(3) 0.0322(9) Uani 1 1 d . . . H27 H 0.3168 0.8109 0.5059 0.039 Uiso 1 1 calc R . . C28 C 0.2332(3) 0.6159(3) 0.4631(3) 0.0265(8) Uani 1 1 d . . . H28 H 0.1813 0.5934 0.5073 0.032 Uiso 1 1 calc R . . C29 C -0.1793(4) -0.0305(3) 0.4812(3) 0.0263(8) Uani 1 1 d . . . H29A H -0.2720 -0.0489 0.4670 0.039 Uiso 1 1 calc R . . H29B H -0.1605 -0.0742 0.5333 0.039 Uiso 1 1 calc R . . H29C H -0.1704 -0.0622 0.4193 0.039 Uiso 1 1 calc R . . C30 C -0.0745(4) 0.1554(4) 0.6183(3) 0.0276(8) Uani 1 1 d . . . H30A H -0.0162 0.2503 0.6380 0.041 Uiso 1 1 calc R . . H30B H -0.0359 0.1181 0.6660 0.041 Uiso 1 1 calc R . . H30C H -0.1656 0.1289 0.6193 0.041 Uiso 1 1 calc R . . C31 C 0.2643(4) 0.3353(4) 0.6747(3) 0.0268(8) Uani 1 1 d . . . H31A H 0.1767 0.2548 0.6615 0.040 Uiso 1 1 calc R . . H31B H 0.2818 0.3970 0.7336 0.040 Uiso 1 1 calc R . . H31C H 0.3367 0.3165 0.6883 0.040 Uiso 1 1 calc R . . C32 C 0.3968(3) 0.4992(4) 0.5983(3) 0.0281(8) Uani 1 1 d . . . H32A H 0.3981 0.5223 0.5331 0.042 Uiso 1 1 calc R . . H32B H 0.4629 0.4735 0.6212 0.042 Uiso 1 1 calc R . . H32C H 0.4203 0.5743 0.6482 0.042 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 0.0156(16) 0.0210(19) 0.0111(18) 0.0035(15) 0.0031(14) 0.0039(15) B2 0.0211(17) 0.0168(18) 0.0091(18) 0.0040(14) 0.0044(14) 0.0067(15) B3 0.0266(19) 0.025(2) 0.0090(18) 0.0018(15) 0.0053(14) 0.0152(16) B4 0.0155(16) 0.026(2) 0.0140(19) 0.0054(16) 0.0024(14) 0.0102(15) B5 0.0237(18) 0.029(2) 0.0085(18) 0.0045(16) 0.0057(14) 0.0161(17) B6 0.0248(18) 0.0215(19) 0.0112(19) 0.0017(15) 0.0055(15) 0.0135(16) N1 0.0188(13) 0.0259(15) 0.0097(14) 0.0049(12) 0.0054(11) 0.0093(12) N2 0.0190(13) 0.0269(15) 0.0106(14) 0.0045(12) 0.0042(11) 0.0101(12) N3 0.0253(14) 0.0256(15) 0.0086(14) 0.0043(11) 0.0033(11) 0.0120(12) N4 0.0239(14) 0.0272(16) 0.0133(14) 0.0085(12) 0.0093(11) 0.0124(13) N5 0.0185(13) 0.0215(15) 0.0076(14) 0.0035(11) 0.0032(10) 0.0068(12) N6 0.0212(13) 0.0183(14) 0.0094(13) 0.0046(11) 0.0042(11) 0.0076(11) N7 0.0259(14) 0.0280(16) 0.0113(14) 0.0059(12) 0.0073(11) 0.0132(13) N8 0.0233(13) 0.0266(16) 0.0115(15) 0.0053(12) 0.0024(11) 0.0120(13) C1 0.0212(16) 0.0229(18) 0.0122(16) 0.0109(14) 0.0073(13) 0.0102(14) C2 0.0234(17) 0.0295(19) 0.0140(17) 0.0080(15) 0.0046(14) 0.0098(15) C3 0.0201(16) 0.0270(19) 0.026(2) 0.0101(16) 0.0062(14) 0.0098(15) C4 0.0283(18) 0.041(2) 0.032(2) 0.0197(18) 0.0176(16) 0.0246(18) C5 0.0348(19) 0.032(2) 0.0165(18) 0.0091(15) 0.0125(15) 0.0193(17) C6 0.0251(17) 0.0262(18) 0.0132(16) 0.0091(14) 0.0067(13) 0.0129(15) C7 0.0138(14) 0.0266(18) 0.0169(17) 0.0086(14) 0.0054(13) 0.0078(14) C8 0.0270(17) 0.0287(19) 0.0179(18) 0.0084(15) 0.0103(14) 0.0137(15) C9 0.0320(19) 0.031(2) 0.033(2) 0.0073(17) 0.0164(16) 0.0167(17) C10 0.0289(19) 0.032(2) 0.043(2) 0.0216(18) 0.0166(17) 0.0188(17) C11 0.0239(17) 0.036(2) 0.026(2) 0.0188(17) 0.0096(15) 0.0152(16) C12 0.0187(15) 0.0304(19) 0.0172(18) 0.0112(15) 0.0078(13) 0.0113(14) C13 0.0230(16) 0.030(2) 0.0196(19) 0.0064(15) 0.0024(14) 0.0118(15) C14 0.0323(18) 0.032(2) 0.0104(17) 0.0047(15) 0.0066(14) 0.0125(16) C15 0.0333(18) 0.031(2) 0.0211(19) 0.0153(16) 0.0160(15) 0.0165(17) C16 0.0242(17) 0.0297(19) 0.0217(19) 0.0094(16) 0.0106(14) 0.0117(15) C17 0.0233(16) 0.0234(18) 0.0087(16) 0.0051(14) 0.0032(13) 0.0077(15) C18 0.0278(18) 0.033(2) 0.0142(17) 0.0098(15) 0.0076(14) 0.0131(16) C19 0.042(2) 0.0224(19) 0.0185(19) 0.0024(15) 0.0095(16) 0.0102(17) C20 0.033(2) 0.024(2) 0.019(2) 0.0027(16) -0.0014(15) 0.0036(16) C21 0.0245(18) 0.032(2) 0.024(2) 0.0112(17) 0.0036(15) 0.0093(16) C22 0.0236(17) 0.0252(18) 0.0207(19) 0.0076(15) 0.0063(14) 0.0097(15) C23 0.0173(15) 0.0231(17) 0.0122(16) 0.0035(14) -0.0031(12) 0.0086(14) C24 0.0189(15) 0.0261(18) 0.0176(18) 0.0078(14) 0.0038(13) 0.0095(14) C25 0.0215(17) 0.036(2) 0.022(2) 0.0164(17) 0.0027(14) 0.0106(16) C26 0.0318(19) 0.027(2) 0.030(2) 0.0110(17) -0.0023(16) 0.0135(17) C27 0.0356(19) 0.0252(19) 0.029(2) 0.0022(16) -0.0005(16) 0.0168(16) C28 0.0280(17) 0.0266(19) 0.0198(19) 0.0051(15) 0.0050(14) 0.0123(15) C29 0.0306(18) 0.0232(18) 0.0227(19) 0.0105(15) 0.0119(15) 0.0104(15) C30 0.0364(19) 0.042(2) 0.0144(18) 0.0118(16) 0.0157(15) 0.0236(18) C31 0.0314(18) 0.028(2) 0.0119(17) 0.0015(15) 0.0003(14) 0.0134(16) C32 0.0222(16) 0.037(2) 0.0178(19) 0.0061(16) 0.0016(14) 0.0130(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 N2 1.440(5) . ? B1 N1 1.462(5) . ? B1 B4 1.722(5) . ? B2 N3 1.405(5) . ? B2 N1 1.474(5) . ? B2 B3 1.723(5) . ? B3 N4 1.405(5) . ? B3 N2 1.475(5) . ? B4 N6 1.451(4) . ? B4 N5 1.457(5) . ? B5 N7 1.409(5) . ? B5 N5 1.474(4) . ? B5 B6 1.718(5) . ? B6 N8 1.404(4) . ? B6 N6 1.485(5) . ? N1 C1 1.421(4) . ? N2 C7 1.421(5) . ? N3 C13 1.456(5) . ? N3 C14 1.469(4) . ? N4 C16 1.458(4) . ? N4 C15 1.464(4) . ? N5 C17 1.428(4) . ? N6 C23 1.430(4) . ? N7 C30 1.455(4) . ? N7 C29 1.456(4) . ? N8 C31 1.454(5) . ? N8 C32 1.459(4) . ? C1 C2 1.396(5) . ? C1 C6 1.398(5) . ? C2 C3 1.381(5) . ? C2 H2 0.9500 . ? C3 C4 1.386(5) . ? C3 H3 0.9500 . ? C4 C5 1.387(5) . ? C4 H4 0.9500 . ? C5 C6 1.384(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.396(5) . ? C7 C8 1.397(5) . ? C8 C9 1.383(5) . ? C8 H8 0.9500 . ? C9 C10 1.394(6) . ? C9 H9 0.9500 . ? C10 C11 1.380(6) . ? C10 H10 0.9500 . ? C11 C12 1.388(5) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C22 1.380(5) . ? C17 C18 1.396(5) . ? C18 C19 1.390(5) . ? C18 H18 0.9500 . ? C19 C20 1.372(6) . ? C19 H19 0.9500 . ? C20 C21 1.393(6) . ? C20 H20 0.9500 . ? C21 C22 1.385(5) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.385(5) . ? C23 C28 1.391(5) . ? C24 C25 1.402(5) . ? C24 H24 0.9500 . ? C25 C26 1.373(6) . ? C25 H25 0.9500 . ? C26 C27 1.383(6) . ? C26 H26 0.9500 . ? C27 C28 1.389(5) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 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 N2 B1 N1 111.6(3) . . ? N2 B1 B4 125.2(3) . . ? N1 B1 B4 123.1(3) . . ? N3 B2 N1 125.4(3) . . ? N3 B2 B3 133.6(3) . . ? N1 B2 B3 100.8(3) . . ? N4 B3 N2 122.2(3) . . ? N4 B3 B2 131.3(3) . . ? N2 B3 B2 103.8(3) . . ? N6 B4 N5 111.6(3) . . ? N6 B4 B1 124.4(3) . . ? N5 B4 B1 123.9(3) . . ? N7 B5 N5 125.7(3) . . ? N7 B5 B6 133.2(3) . . ? N5 B5 B6 101.0(3) . . ? N8 B6 N6 122.6(3) . . ? N8 B6 B5 130.8(3) . . ? N6 B6 B5 104.1(3) . . ? C1 N1 B1 118.5(3) . . ? C1 N1 B2 129.3(3) . . ? B1 N1 B2 111.0(3) . . ? C7 N2 B1 125.2(3) . . ? C7 N2 B3 126.6(3) . . ? B1 N2 B3 108.2(3) . . ? B2 N3 C13 126.7(3) . . ? B2 N3 C14 122.5(3) . . ? C13 N3 C14 110.8(3) . . ? B3 N4 C16 125.6(3) . . ? B3 N4 C15 123.5(3) . . ? C16 N4 C15 110.4(3) . . ? C17 N5 B4 119.3(3) . . ? C17 N5 B5 127.7(3) . . ? B4 N5 B5 111.4(3) . . ? C23 N6 B4 125.3(3) . . ? C23 N6 B6 126.7(3) . . ? B4 N6 B6 107.9(3) . . ? B5 N7 C30 122.5(3) . . ? B5 N7 C29 126.5(3) . . ? C30 N7 C29 111.0(3) . . ? B6 N8 C31 123.4(3) . . ? B6 N8 C32 126.0(3) . . ? C31 N8 C32 110.4(3) . . ? C2 C1 C6 118.4(3) . . ? C2 C1 N1 120.9(3) . . ? C6 C1 N1 120.7(3) . . ? C3 C2 C1 120.7(3) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 120.6(3) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 119.2(3) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 120.5(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 120.6(3) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? C12 C7 C8 118.1(3) . . ? C12 C7 N2 122.8(3) . . ? C8 C7 N2 119.1(3) . . ? C9 C8 C7 121.3(3) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C9 C10 120.0(3) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 119.1(4) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C10 C11 C12 121.0(3) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C11 C12 C7 120.5(3) . . ? C11 C12 H12 119.8 . . ? C7 C12 H12 119.8 . . ? N3 C13 H13A 109.5 . . ? N3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 H14A 109.5 . . ? N3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N4 C15 H15A 109.5 . . ? N4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N4 C16 H16A 109.5 . . ? N4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 119.1(3) . . ? C22 C17 N5 120.6(3) . . ? C18 C17 N5 120.2(3) . . ? C19 C18 C17 119.5(3) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C20 C19 C18 121.4(4) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C19 C20 C21 118.8(3) . . ? C19 C20 H20 120.6 . . ? C21 C20 H20 120.6 . . ? C22 C21 C20 120.3(4) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C17 C22 C21 120.8(3) . . ? C17 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C24 C23 C28 119.0(3) . . ? C24 C23 N6 122.3(3) . . ? C28 C23 N6 118.7(3) . . ? C23 C24 C25 119.7(3) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C26 C25 C24 121.0(4) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C25 C26 C27 119.3(4) . . ? C25 C26 H26 120.3 . . ? C27 C26 H26 120.3 . . ? C26 C27 C28 120.2(4) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C27 C28 C23 120.7(4) . . ? C27 C28 H28 119.6 . . ? C23 C28 H28 119.6 . . ? N7 C29 H29A 109.5 . . ? N7 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N7 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N7 C30 H30A 109.5 . . ? N7 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N7 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N8 C31 H31A 109.5 . . ? N8 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N8 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N8 C32 H32A 109.5 . . ? N8 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N8 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? 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 N3 B2 B3 N4 33.4(6) . . . . ? N1 B2 B3 N4 -141.6(4) . . . . ? N3 B2 B3 N2 -165.5(4) . . . . ? N1 B2 B3 N2 19.6(3) . . . . ? N2 B1 B4 N6 81.7(4) . . . . ? N1 B1 B4 N6 -95.7(4) . . . . ? N2 B1 B4 N5 -95.1(4) . . . . ? N1 B1 B4 N5 87.4(4) . . . . ? N7 B5 B6 N8 32.7(6) . . . . ? N5 B5 B6 N8 -143.1(4) . . . . ? N7 B5 B6 N6 -165.7(4) . . . . ? N5 B5 B6 N6 18.5(3) . . . . ? N2 B1 N1 C1 167.2(3) . . . . ? B4 B1 N1 C1 -15.1(5) . . . . ? N2 B1 N1 B2 -1.2(4) . . . . ? B4 B1 N1 B2 176.6(3) . . . . ? N3 B2 N1 C1 6.6(6) . . . . ? B3 B2 N1 C1 -178.0(3) . . . . ? N3 B2 N1 B1 173.3(3) . . . . ? B3 B2 N1 B1 -11.2(3) . . . . ? N1 B1 N2 C7 -162.4(3) . . . . ? B4 B1 N2 C7 19.9(5) . . . . ? N1 B1 N2 B3 15.5(4) . . . . ? B4 B1 N2 B3 -162.2(3) . . . . ? N4 B3 N2 C7 -39.9(5) . . . . ? B2 B3 N2 C7 156.7(3) . . . . ? N4 B3 N2 B1 142.2(3) . . . . ? B2 B3 N2 B1 -21.2(3) . . . . ? N1 B2 N3 C13 17.5(6) . . . . ? B3 B2 N3 C13 -156.3(4) . . . . ? N1 B2 N3 C14 -163.0(3) . . . . ? B3 B2 N3 C14 23.2(6) . . . . ? N2 B3 N4 C16 -1.4(5) . . . . ? B2 B3 N4 C16 156.9(3) . . . . ? N2 B3 N4 C15 -172.6(3) . . . . ? B2 B3 N4 C15 -14.3(5) . . . . ? N6 B4 N5 C17 166.7(3) . . . . ? B1 B4 N5 C17 -16.1(5) . . . . ? N6 B4 N5 B5 -0.1(4) . . . . ? B1 B4 N5 B5 177.1(3) . . . . ? N7 B5 N5 C17 7.2(6) . . . . ? B6 B5 N5 C17 -176.6(3) . . . . ? N7 B5 N5 B4 172.6(3) . . . . ? B6 B5 N5 B4 -11.2(3) . . . . ? N5 B4 N6 C23 -165.3(3) . . . . ? B1 B4 N6 C23 17.6(5) . . . . ? N5 B4 N6 B6 13.6(4) . . . . ? B1 B4 N6 B6 -163.6(3) . . . . ? N8 B6 N6 C23 -37.0(5) . . . . ? B5 B6 N6 C23 159.5(3) . . . . ? N8 B6 N6 B4 144.2(3) . . . . ? B5 B6 N6 B4 -19.3(3) . . . . ? N5 B5 N7 C30 -160.5(3) . . . . ? B6 B5 N7 C30 24.6(6) . . . . ? N5 B5 N7 C29 19.5(6) . . . . ? B6 B5 N7 C29 -155.4(4) . . . . ? N6 B6 N8 C31 -171.7(3) . . . . ? B5 B6 N8 C31 -13.0(6) . . . . ? N6 B6 N8 C32 2.3(5) . . . . ? B5 B6 N8 C32 161.0(3) . . . . ? B1 N1 C1 C2 -112.8(4) . . . . ? B2 N1 C1 C2 53.2(5) . . . . ? B1 N1 C1 C6 64.9(4) . . . . ? B2 N1 C1 C6 -129.2(4) . . . . ? C6 C1 C2 C3 -0.4(5) . . . . ? N1 C1 C2 C3 177.3(3) . . . . ? C1 C2 C3 C4 0.9(6) . . . . ? C2 C3 C4 C5 -1.3(6) . . . . ? C3 C4 C5 C6 1.3(6) . . . . ? C4 C5 C6 C1 -0.8(6) . . . . ? C2 C1 C6 C5 0.3(5) . . . . ? N1 C1 C6 C5 -177.4(3) . . . . ? B1 N2 C7 C12 -44.0(5) . . . . ? B3 N2 C7 C12 138.4(3) . . . . ? B1 N2 C7 C8 134.9(3) . . . . ? B3 N2 C7 C8 -42.6(5) . . . . ? C12 C7 C8 C9 -1.5(5) . . . . ? N2 C7 C8 C9 179.5(3) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C8 C9 C10 C11 1.0(6) . . . . ? C9 C10 C11 C12 -1.0(6) . . . . ? C10 C11 C12 C7 -0.2(5) . . . . ? C8 C7 C12 C11 1.5(5) . . . . ? N2 C7 C12 C11 -179.6(3) . . . . ? B4 N5 C17 C22 -110.1(4) . . . . ? B5 N5 C17 C22 54.4(5) . . . . ? B4 N5 C17 C18 67.7(5) . . . . ? B5 N5 C17 C18 -127.9(4) . . . . ? C22 C17 C18 C19 -1.2(6) . . . . ? N5 C17 C18 C19 -178.9(3) . . . . ? C17 C18 C19 C20 -1.0(6) . . . . ? C18 C19 C20 C21 2.2(6) . . . . ? C19 C20 C21 C22 -1.2(6) . . . . ? C18 C17 C22 C21 2.1(6) . . . . ? N5 C17 C22 C21 179.9(3) . . . . ? C20 C21 C22 C17 -0.9(6) . . . . ? B4 N6 C23 C24 -47.1(5) . . . . ? B6 N6 C23 C24 134.3(3) . . . . ? B4 N6 C23 C28 133.6(3) . . . . ? B6 N6 C23 C28 -45.0(5) . . . . ? C28 C23 C24 C25 1.4(5) . . . . ? N6 C23 C24 C25 -177.9(3) . . . . ? C23 C24 C25 C26 0.8(5) . . . . ? C24 C25 C26 C27 -2.5(5) . . . . ? C25 C26 C27 C28 1.9(6) . . . . ? C26 C27 C28 C23 0.3(5) . . . . ? C24 C23 C28 C27 -1.9(5) . . . . ? N6 C23 C28 C27 177.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 65.83 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.442 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.076