# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'A. Cowley' 'Michael Findlater' 'Adam Powell' 'Ignacio Vargas-Baca' _publ_contact_author_name 'Dr Alan Cowley' _publ_contact_author_email COWLEY@MAIL.UTEXAS.EDU _publ_section_title ; Boron di- and trications ; # Attachment 'Dibromoborane_6.cif' data_pnma _database_code_depnum_ccdc_archive 'CCDC 692492' _audit_creation_method 'SHELXTL Ver. 6.10' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 H10 B Br2 N' _chemical_formula_sum 'C3 H10 B Br2 N' _chemical_formula_weight 230.75 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma _symmetry_space_group_name_Hall -p2ac2n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 11.627(5) _cell_length_b 10.811(5) _cell_length_c 6.171(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 775.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.976 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 10.348 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min .301 _exptl_absorpt_correction_T_max .394 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2753 _diffrn_reflns_av_R_equivalents 0.0575 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 27.44 _reflns_number_total 918 _reflns_number_gt 497 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+0.2507P] 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 918 _refine_ls_number_parameters 37 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0913 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1085 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _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 Br1 Br 0.86569(4) 0.90213(4) 0.49373(8) 0.0441(3) Uani 1 1 d . . . N1 N 0.6557(5) 0.7500 0.5559(8) 0.0313(13) Uani 1 2 d S . . C1 C 0.6697(6) 0.7500 0.7960(9) 0.0388(17) Uani 1 2 d S . . H1A H 0.7114 0.8225 0.8395 0.047 Uiso 1 1 d R . . H1C H 0.5953 0.7500 0.8634 0.047 Uiso 1 2 d SR . . C2 C 0.5865(5) 0.6366(5) 0.4959(7) 0.0486(14) Uani 1 1 d . . . H2A H 0.5153 0.6367 0.5747 0.073 Uiso 1 1 d R . . H2B H 0.6293 0.5633 0.5313 0.073 Uiso 1 1 d R . . H2C H 0.5707 0.6377 0.3432 0.073 Uiso 1 1 d R . . B1 B 0.7714(7) 0.7500 0.4159(13) 0.035(2) Uani 1 2 d S . . H1 H 0.7533 0.7500 0.2609 0.042 Uiso 1 2 d SR . . 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 Br1 0.0384(4) 0.0304(3) 0.0635(4) 0.0065(2) 0.0017(3) -0.0072(2) N1 0.028(3) 0.026(3) 0.040(3) 0.000 -0.001(2) 0.000 C1 0.041(4) 0.040(4) 0.035(4) 0.000 -0.001(3) 0.000 C2 0.038(3) 0.046(3) 0.062(4) -0.003(3) -0.001(3) -0.013(3) B1 0.034(5) 0.030(5) 0.040(4) 0.000 0.002(4) 0.000 _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 Br1 B1 2.034(5) . ? N1 C1 1.490(7) . ? N1 C2 1.513(6) . ? N1 C2 1.513(6) 8_575 ? N1 B1 1.599(10) . ? C1 H1A 0.9597 . ? C1 H1C 0.9598 . ? C2 H2A 0.9603 . ? C2 H2B 0.9602 . ? C2 H2C 0.9600 . ? B1 Br1 2.034(5) 8_575 ? B1 H1 0.9794 . ? 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 C2 107.6(3) . . ? C1 N1 C2 107.6(3) . 8_575 ? C2 N1 C2 108.3(6) . 8_575 ? C1 N1 B1 116.4(6) . . ? C2 N1 B1 108.4(3) . . ? C2 N1 B1 108.4(3) 8_575 . ? N1 C1 H1A 109.5 . . ? N1 C1 H1C 109.4 . . ? H1A C1 H1C 109.5 . . ? N1 C2 H2A 109.4 . . ? N1 C2 H2B 109.7 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.4 . . ? H2A C2 H2C 109.4 . . ? H2B C2 H2C 109.5 . . ? N1 B1 Br1 109.0(3) . . ? N1 B1 Br1 109.0(3) . 8_575 ? Br1 B1 Br1 107.9(4) . 8_575 ? N1 B1 H1 110.3 . . ? Br1 B1 H1 110.3 . . ? Br1 B1 H1 110.3 8_575 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.784 _refine_diff_density_min -0.603 _refine_diff_density_rms 0.121 # Attachment 'Dication_7.cif' data_texas087 _database_code_depnum_ccdc_archive 'CCDC 692493' _audit_creation_method 'SHELXTL Ver. 6.10' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H16 B N3, 2(H2 O), 2(Br)' _chemical_formula_sum 'C15 H20 B Br2 N3 O2' _chemical_formula_weight 444.97 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' Br Br -0.2901 2.4595 '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 9.3043(4) _cell_length_b 10.0118(4) _cell_length_c 12.0149(8) _cell_angle_alpha 93.085(3) _cell_angle_beta 112.533(3) _cell_angle_gamma 117.583(2) _cell_volume 878.96(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.681 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 4.623 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.246 _exptl_absorpt_correction_T_max 0.379 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19540 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4019 _reflns_number_gt 3833 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0105P)^2^+1.6077P] 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 0.0000 _refine_ls_number_reflns 4019 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0302 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0603 _refine_ls_wR_factor_gt 0.0590 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.6744(5) 0.8305(4) 0.7958(4) 0.0191(7) Uani 1 1 d . . . N1 N 0.6912(4) 0.8249(4) 0.6697(3) 0.0228(7) Uani 1 1 d . . . C1 C 0.6989(5) 0.7114(5) 0.6110(4) 0.0284(9) Uani 1 1 d . . . H1 H 0.6827 0.6228 0.6421 0.053(15) Uiso 1 1 calc R . . C2 C 0.7292(6) 0.7199(6) 0.5091(4) 0.0370(10) Uani 1 1 d . . . H2 H 0.7330 0.6381 0.4690 0.067(17) Uiso 1 1 calc R . . C3 C 0.7535(5) 0.8448(6) 0.4656(4) 0.0396(11) Uani 1 1 d . . . H3 H 0.7762 0.8516 0.3948 0.052(14) Uiso 1 1 calc R . . C4 C 0.7461(6) 0.9665(6) 0.5229(5) 0.0448(15) Uani 1 1 d . . . H4 H 0.7612 1.0546 0.4915 0.040(13) Uiso 1 1 calc R . . C5 C 0.7156(5) 0.9516(5) 0.6285(4) 0.0299(9) Uani 1 1 d . . . H5 H 0.7122 1.0320 0.6711 0.034(12) Uiso 1 1 calc R . . N2 N 0.4752(4) 0.7820(3) 0.7670(3) 0.0222(6) Uani 1 1 d . . . C6 C 0.3346(5) 0.7272(4) 0.6518(3) 0.0237(8) Uani 1 1 d . . . H6 H 0.3488 0.7034 0.5805 0.041(12) Uiso 1 1 calc R . . C7 C 0.1677(5) 0.7048(4) 0.6357(4) 0.0225(8) Uani 1 1 d . . . H7 H 0.0687 0.6672 0.5538 0.022(10) Uiso 1 1 calc R . . C8 C 0.1479(5) 0.7380(4) 0.7407(4) 0.0231(7) Uani 1 1 d . . . H8 H 0.0357 0.7247 0.7318 0.022(9) Uiso 1 1 calc R . . C9 C 0.2937(5) 0.7908(4) 0.8582(4) 0.0220(8) Uani 1 1 d . . . H9 H 0.2821 0.8117 0.9314 0.041(13) Uiso 1 1 calc R . . C10 C 0.4518(5) 0.8122(4) 0.8681(3) 0.0228(7) Uani 1 1 d . . . H10 H 0.5519 0.8503 0.9495 0.035(12) Uiso 1 1 calc R . . N3 N 0.7221(4) 0.7143(4) 0.8617(3) 0.0219(7) Uani 1 1 d . . . C11 C 0.5984(5) 0.5741(4) 0.8644(3) 0.0217(7) Uani 1 1 d . . . H11 H 0.4717 0.5339 0.8151 0.027(10) Uiso 1 1 calc R . . C12 C 0.6526(5) 0.4890(4) 0.9372(3) 0.0217(8) Uani 1 1 d . . . H12 H 0.5646 0.3905 0.9379 0.037(12) Uiso 1 1 calc R . . C13 C 0.8375(6) 0.5487(5) 1.0094(3) 0.0251(9) Uani 1 1 d . . . H13 H 0.8779 0.4926 1.0616 0.040(12) Uiso 1 1 calc R . . C14 C 0.9617(5) 0.6899(4) 1.0045(3) 0.0231(7) Uani 1 1 d . . . H14 H 1.0890 0.7310 1.0522 0.028(10) Uiso 1 1 calc R . . C15 C 0.9025(5) 0.7712(4) 0.9312(4) 0.0228(8) Uani 1 1 d . . . H15 H 0.9893 0.8693 0.9289 0.039(13) Uiso 1 1 calc R . . Br1 Br 0.18796(5) 0.10274(4) 0.82495(3) 0.01723(8) Uani 1 1 d . . . Br2 Br 0.76474(4) 0.37514(4) 0.67406(3) 0.02060(8) Uani 1 1 d . . . O1 O 0.1439(4) 0.3782(3) 0.6959(3) 0.0262(6) Uani 1 1 d . . . H1AO H 0.1447 0.3094 0.7343 0.026(11) Uiso 1 1 d R . . H1BO H 0.0494 0.3809 0.6846 0.024(10) Uiso 1 1 d R . . O2 O 0.4338(3) 0.8720(3) 0.1835(3) 0.0258(6) Uani 1 1 d . . . H2BO H 0.5297 0.8738 0.1918 0.050(15) Uiso 1 1 d R . . H2AO H 0.3906 0.8019 0.2180 0.039(13) Uiso 1 1 d R . . H1B H 0.768(5) 0.951(4) 0.858(3) 0.020(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0191(18) 0.0181(18) 0.0218(18) 0.0067(15) 0.0103(15) 0.0102(15) N1 0.0221(15) 0.0354(17) 0.0268(16) 0.0205(14) 0.0168(13) 0.0209(14) C1 0.0183(18) 0.031(2) 0.032(2) 0.0052(17) 0.0059(16) 0.0153(16) C2 0.028(2) 0.060(3) 0.026(2) 0.008(2) 0.0085(17) 0.028(2) C3 0.0203(19) 0.066(3) 0.026(2) 0.010(2) 0.0133(17) 0.016(2) C4 0.020(2) 0.043(3) 0.043(3) 0.035(2) 0.0026(19) 0.0030(19) C5 0.031(2) 0.0284(19) 0.0261(19) 0.0088(16) 0.0054(16) 0.0184(17) N2 0.0243(14) 0.0309(16) 0.0252(15) 0.0165(13) 0.0150(13) 0.0206(13) C6 0.033(2) 0.0288(19) 0.0239(18) 0.0140(15) 0.0174(16) 0.0227(16) C7 0.0207(18) 0.0154(17) 0.0183(17) 0.0041(14) 0.0000(14) 0.0071(14) C8 0.0204(18) 0.0185(15) 0.041(2) 0.0157(14) 0.0197(17) 0.0127(14) C9 0.0279(19) 0.0180(16) 0.0256(19) 0.0102(14) 0.0161(16) 0.0125(15) C10 0.0208(17) 0.0289(18) 0.0191(16) 0.0152(14) 0.0099(14) 0.0120(15) N3 0.0204(15) 0.0320(17) 0.0223(15) 0.0157(13) 0.0137(12) 0.0165(13) C11 0.0168(16) 0.0278(18) 0.0152(15) 0.0039(13) 0.0083(13) 0.0074(14) C12 0.0272(19) 0.0185(16) 0.0241(18) 0.0067(14) 0.0173(16) 0.0109(14) C13 0.046(2) 0.0318(19) 0.0186(17) 0.0144(16) 0.0205(17) 0.0302(18) C14 0.0161(16) 0.0289(18) 0.0201(17) -0.0034(14) 0.0039(13) 0.0132(14) C15 0.0214(18) 0.0172(16) 0.033(2) 0.0071(15) 0.0195(16) 0.0071(14) Br1 0.01830(16) 0.01834(14) 0.01795(15) 0.00768(11) 0.00961(13) 0.01044(13) Br2 0.01748(17) 0.02243(15) 0.01964(16) 0.00792(12) 0.00899(14) 0.00830(14) O1 0.0289(14) 0.0277(13) 0.0363(16) 0.0191(12) 0.0201(12) 0.0201(12) O2 0.0232(14) 0.0268(13) 0.0345(15) 0.0182(12) 0.0166(12) 0.0146(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 1.565(4) . ? B1 N3 1.577(5) . ? B1 N1 1.583(5) . ? B1 H1B 1.10(4) . ? N1 C5 1.339(5) . ? N1 C1 1.350(5) . ? C1 C2 1.357(6) . ? C1 H1 0.9500 . ? C2 C3 1.336(7) . ? C2 H2 0.9500 . ? C3 C4 1.410(8) . ? C3 H3 0.9500 . ? C4 C5 1.404(7) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? N2 C6 1.339(5) . ? N2 C10 1.355(5) . ? C6 C7 1.393(6) . ? C6 H6 0.9500 . ? C7 C8 1.389(6) . ? C7 H7 0.9500 . ? C8 C9 1.378(6) . ? C8 H8 0.9500 . ? C9 C10 1.340(6) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? N3 C15 1.352(5) . ? N3 C11 1.354(5) . ? C11 C12 1.373(5) . ? C11 H11 0.9500 . ? C12 C13 1.384(6) . ? C12 H12 0.9500 . ? C13 C14 1.373(5) . ? C13 H13 0.9500 . ? C14 C15 1.366(5) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? O1 H1AO 0.8500 . ? O1 H1BO 0.8500 . ? O2 H2BO 0.8501 . ? O2 H2AO 0.8500 . ? 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 N3 109.1(3) . . ? N2 B1 N1 110.0(3) . . ? N3 B1 N1 109.9(3) . . ? N2 B1 H1B 108(2) . . ? N3 B1 H1B 110(2) . . ? N1 B1 H1B 109.1(19) . . ? C5 N1 C1 120.1(3) . . ? C5 N1 B1 114.9(3) . . ? C1 N1 B1 124.7(3) . . ? N1 C1 C2 122.0(4) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C3 C2 C1 119.3(5) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 121.2(4) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 116.9(4) . . ? C5 C4 H4 121.5 . . ? C3 C4 H4 121.5 . . ? N1 C5 C4 120.5(4) . . ? N1 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C6 N2 C10 119.1(3) . . ? C6 N2 B1 125.0(3) . . ? C10 N2 B1 115.7(3) . . ? N2 C6 C7 120.6(3) . . ? N2 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 119.2(3) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C9 C8 C7 118.9(3) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C10 C9 C8 119.4(3) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 N2 122.9(3) . . ? C9 C10 H10 118.6 . . ? N2 C10 H10 118.6 . . ? C15 N3 C11 119.4(3) . . ? C15 N3 B1 115.2(3) . . ? C11 N3 B1 124.9(3) . . ? N3 C11 C12 121.3(3) . . ? N3 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C11 C12 C13 119.1(3) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C14 C13 C12 119.2(3) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C15 C14 C13 120.0(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? N3 C15 C14 121.0(3) . . ? N3 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? H1AO O1 H1BO 107.5 . . ? H2BO O2 H2AO 102.8 . . ? 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 C5 81.5(4) . . . . ? N3 B1 N1 C5 -158.3(3) . . . . ? N2 B1 N1 C1 -104.7(4) . . . . ? N3 B1 N1 C1 15.5(5) . . . . ? C5 N1 C1 C2 -0.7(6) . . . . ? B1 N1 C1 C2 -174.2(3) . . . . ? N1 C1 C2 C3 0.5(6) . . . . ? C1 C2 C3 C4 -0.8(6) . . . . ? C2 C3 C4 C5 1.1(6) . . . . ? C1 N1 C5 C4 1.1(6) . . . . ? B1 N1 C5 C4 175.2(3) . . . . ? C3 C4 C5 N1 -1.3(6) . . . . ? N3 B1 N2 C6 -114.0(4) . . . . ? N1 B1 N2 C6 6.7(4) . . . . ? N3 B1 N2 C10 72.1(4) . . . . ? N1 B1 N2 C10 -167.2(3) . . . . ? C10 N2 C6 C7 1.4(5) . . . . ? B1 N2 C6 C7 -172.3(3) . . . . ? N2 C6 C7 C8 -0.8(5) . . . . ? C6 C7 C8 C9 -0.7(6) . . . . ? C7 C8 C9 C10 1.6(6) . . . . ? C8 C9 C10 N2 -1.1(6) . . . . ? C6 N2 C10 C9 -0.5(5) . . . . ? B1 N2 C10 C9 173.8(3) . . . . ? N2 B1 N3 C15 -157.2(3) . . . . ? N1 B1 N3 C15 82.1(4) . . . . ? N2 B1 N3 C11 15.2(5) . . . . ? N1 B1 N3 C11 -105.6(4) . . . . ? C15 N3 C11 C12 0.5(5) . . . . ? B1 N3 C11 C12 -171.5(3) . . . . ? N3 C11 C12 C13 0.3(6) . . . . ? C11 C12 C13 C14 -1.3(6) . . . . ? C12 C13 C14 C15 1.4(6) . . . . ? C11 N3 C15 C14 -0.3(6) . . . . ? B1 N3 C15 C14 172.4(3) . . . . ? C13 C14 C15 N3 -0.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.783 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.083 # Attachment 'Tribromoborane_2.cif' data_ccdkvap075x _database_code_depnum_ccdc_archive 'CCDC 692494' _audit_creation_method 'SHELXTL Ver. 6.10' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 H9 B Br3 N' _chemical_formula_sum 'C3 H9 B Br3 N' _chemical_formula_weight 309.65 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p21/m _symmetry_space_group_name_Hall -p2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 6.626(5) _cell_length_b 10.493(5) _cell_length_c 6.810(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 115.211(5) _cell_angle_gamma 90.000(5) _cell_volume 428.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 14.037 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min .060 _exptl_absorpt_correction_T_max .122 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1631 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 27.38 _reflns_number_total 1023 _reflns_number_gt 871 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.9736P] 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 1023 _refine_ls_number_parameters 43 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0925 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.920 _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 C1 C 0.4648(8) 0.3659(5) 1.2603(7) 0.0290(10) Uani 1 1 d . . . H1A H 0.5973 0.3686 1.2311 0.043 Uiso 1 1 calc R . . H1B H 0.5108 0.3614 1.4173 0.043 Uiso 1 1 calc R . . H1C H 0.3755 0.4429 1.2023 0.043 Uiso 1 1 calc R . . C2 C 0.1270(10) 0.2500 1.2014(10) 0.0251(13) Uani 1 2 d S . . H2A H 0.0341 0.1755 1.1336 0.038 Uiso 0.50 1 calc PR . . H2B H 0.0404 0.3279 1.1436 0.038 Uiso 0.50 1 calc PR . . H2C H 0.1754 0.2465 1.3588 0.038 Uiso 1 0.5 calc SR . . B1 B 0.2611(11) 0.2500 0.8987(10) 0.0184(13) Uani 1 2 d S . . N1 N 0.3272(8) 0.2500 1.1528(8) 0.0188(10) Uani 1 2 d S . . Br1 Br 0.53518(11) 0.2500 0.84432(10) 0.0303(2) Uani 1 2 d S . . Br2 Br 0.07542(8) 0.40523(4) 0.75749(7) 0.02899(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.029(2) 0.028(2) 0.025(2) -0.0081(19) 0.0073(19) -0.014(2) C2 0.020(3) 0.031(3) 0.028(3) 0.000 0.013(3) 0.000 B1 0.019(3) 0.018(3) 0.019(3) 0.000 0.008(3) 0.000 N1 0.017(2) 0.018(2) 0.020(2) 0.000 0.0059(19) 0.000 Br1 0.0216(4) 0.0455(4) 0.0257(3) 0.000 0.0120(3) 0.000 Br2 0.0312(3) 0.0225(3) 0.0278(3) 0.00757(17) 0.0073(2) 0.00685(17) _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 C1 N1 1.509(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N1 1.498(7) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? B1 N1 1.594(8) . ? B1 Br1 2.002(7) . ? B1 Br2 2.021(4) 4_565 ? B1 Br2 2.021(4) . ? N1 C1 1.509(5) 4_565 ? 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 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 B1 Br1 110.4(4) . . ? N1 B1 Br2 110.3(2) . 4_565 ? Br1 B1 Br2 109.2(2) . 4_565 ? N1 B1 Br2 110.3(2) . . ? Br1 B1 Br2 109.2(2) . . ? Br2 B1 Br2 107.4(3) 4_565 . ? C2 N1 C1 107.5(3) . . ? C2 N1 C1 107.5(3) . 4_565 ? C1 N1 C1 107.4(5) . 4_565 ? C2 N1 B1 112.3(5) . . ? C1 N1 B1 110.9(3) . . ? C1 N1 B1 110.9(3) 4_565 . ? 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 Br1 B1 N1 C2 180.000(3) . . . . ? Br2 B1 N1 C2 -59.2(3) 4_565 . . . ? Br2 B1 N1 C2 59.2(3) . . . . ? Br1 B1 N1 C1 59.6(3) . . . . ? Br2 B1 N1 C1 -179.6(3) 4_565 . . . ? Br2 B1 N1 C1 -61.1(5) . . . . ? Br1 B1 N1 C1 -59.6(3) . . . 4_565 ? Br2 B1 N1 C1 61.1(5) 4_565 . . 4_565 ? Br2 B1 N1 C1 179.6(3) . . . 4_565 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.38 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.680 _refine_diff_density_min -1.300 _refine_diff_density_rms 0.213 # Attachment 'Trication_5.cif' data_vrecollectsqueeze _database_code_depnum_ccdc_archive 'CCDC 692495' _audit_creation_method 'SHELXTL Ver. 6.10' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 B Br3 N4' _chemical_formula_sum 'C24 H28 B Br3 N4' _chemical_formula_weight 623.04 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p21/c _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.704(4) _cell_length_b 17.664(4) _cell_length_c 18.891(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.60(3) _cell_angle_gamma 90.00 _cell_volume 5825(2) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2480 _exptl_absorpt_coefficient_mu 4.172 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.477 _exptl_absorpt_correction_T_max 0.606 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23787 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0593 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 27.50 _reflns_number_total 13255 _reflns_number_gt 8909 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+8.0435P] 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 13255 _refine_ls_number_parameters 585 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0962 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1690 _refine_ls_wR_factor_gt 0.1552 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 C1 C 1.0874(3) 0.5537(3) 0.1587(3) 0.0281(11) Uani 1 1 d . . . H1 H 1.1125 0.5972 0.1778 0.034 Uiso 1 1 calc R . . C2 C 1.1118(3) 0.5190(3) 0.1013(3) 0.0311(11) Uani 1 1 d . . . H2 H 1.1531 0.5388 0.0828 0.037 Uiso 1 1 calc R . . C3 C 1.0751(3) 0.4544(3) 0.0710(3) 0.0347(12) Uani 1 1 d . . . C4 C 1.0133(3) 0.4298(3) 0.0997(3) 0.0471(15) Uani 1 1 d . . . H4 H 0.9861 0.3877 0.0798 0.057 Uiso 1 1 calc R . . C5 C 0.9904(3) 0.4657(3) 0.1571(3) 0.0414(14) Uani 1 1 d . . . H5 H 0.9480 0.4476 0.1750 0.050 Uiso 1 1 calc R . . C6 C 1.0998(3) 0.4145(4) 0.0090(3) 0.0451(15) Uani 1 1 d . . . H6A H 1.1259 0.3685 0.0255 0.068 Uiso 1 1 calc R . . H6B H 1.1337 0.4465 -0.0122 0.068 Uiso 1 1 calc R . . H6C H 1.0557 0.4026 -0.0261 0.068 Uiso 1 1 calc R . . C7 C 1.1287(3) 0.5896(3) 0.3148(3) 0.0308(11) Uani 1 1 d . . . H7 H 1.1393 0.5423 0.2972 0.037 Uiso 1 1 calc R . . C8 C 1.1841(3) 0.6266(3) 0.3610(3) 0.0345(12) Uani 1 1 d . . . H8 H 1.2321 0.6043 0.3736 0.041 Uiso 1 1 calc R . . C9 C 1.1704(3) 0.6970(3) 0.3898(3) 0.0287(11) Uani 1 1 d . . . C10 C 1.0965(3) 0.7255(3) 0.3707(3) 0.0301(11) Uani 1 1 d . . . H10 H 1.0837 0.7711 0.3901 0.036 Uiso 1 1 calc R . . C11 C 1.0420(3) 0.6871(3) 0.3235(3) 0.0287(11) Uani 1 1 d . . . H11 H 0.9930 0.7073 0.3115 0.034 Uiso 1 1 calc R . . C12 C 1.2300(3) 0.7380(3) 0.4399(3) 0.0366(12) Uani 1 1 d . . . H12A H 1.2377 0.7872 0.4208 0.055 Uiso 1 1 calc R . . H12B H 1.2771 0.7100 0.4457 0.055 Uiso 1 1 calc R . . H12C H 1.2137 0.7433 0.4856 0.055 Uiso 1 1 calc R . . C13 C 0.9869(3) 0.4510(3) 0.3175(3) 0.0433(14) Uani 1 1 d . . . H13 H 1.0225 0.4298 0.2922 0.052 Uiso 1 1 calc R . . C14 C 0.9626(4) 0.4099(3) 0.3712(4) 0.0527(18) Uani 1 1 d . . . H14 H 0.9815 0.3613 0.3815 0.063 Uiso 1 1 calc R . . C15 C 0.9100(4) 0.4404(3) 0.4104(3) 0.0447(15) Uani 1 1 d . . . C16 C 0.8817(3) 0.5116(3) 0.3916(3) 0.0368(13) Uani 1 1 d . . . H16 H 0.8449 0.5331 0.4151 0.044 Uiso 1 1 calc R . . C17 C 0.9085(3) 0.5507(3) 0.3378(3) 0.0304(11) Uani 1 1 d . . . H17 H 0.8899 0.5992 0.3266 0.037 Uiso 1 1 calc R . . C18 C 0.8834(4) 0.3964(4) 0.4688(4) 0.073(3) Uani 1 1 d . . . H18A H 0.9242 0.3928 0.5091 0.109 Uiso 1 1 calc R . . H18B H 0.8685 0.3465 0.4517 0.109 Uiso 1 1 calc R . . H18C H 0.8403 0.4215 0.4832 0.109 Uiso 1 1 calc R . . C19 C 0.8581(3) 0.5961(3) 0.1850(3) 0.0339(12) Uani 1 1 d . . . H19 H 0.8454 0.5504 0.2044 0.041 Uiso 1 1 calc R . . C20 C 0.8030(3) 0.6346(3) 0.1390(3) 0.0353(12) Uani 1 1 d . . . H20 H 0.7538 0.6148 0.1281 0.042 Uiso 1 1 calc R . . C21 C 0.8203(3) 0.7034(3) 0.1086(2) 0.0274(10) Uani 1 1 d . . . C22 C 0.8954(3) 0.7280(3) 0.1262(3) 0.0287(11) Uani 1 1 d . . . H22 H 0.9100 0.7727 0.1063 0.034 Uiso 1 1 calc R . . C23 C 0.9485(3) 0.6882(3) 0.1722(3) 0.0255(10) Uani 1 1 d . . . H23 H 0.9984 0.7064 0.1828 0.031 Uiso 1 1 calc R . . C24 C 0.7617(3) 0.7452(3) 0.0582(3) 0.0374(12) Uani 1 1 d . . . H24A H 0.7548 0.7946 0.0771 0.056 Uiso 1 1 calc R . . H24B H 0.7141 0.7181 0.0523 0.056 Uiso 1 1 calc R . . H24C H 0.7783 0.7498 0.0125 0.056 Uiso 1 1 calc R . . C25 C 0.5930(3) 0.7255(3) 0.2104(2) 0.0247(10) Uani 1 1 d . . . H25 H 0.6263 0.7060 0.2495 0.030 Uiso 1 1 calc R . . C26 C 0.6180(3) 0.7832(3) 0.1715(3) 0.0271(10) Uani 1 1 d . . . H26 H 0.6674 0.8021 0.1841 0.033 Uiso 1 1 calc R . . C27 C 0.5686(3) 0.8136(3) 0.1125(3) 0.0269(11) Uani 1 1 d . . . C28 C 0.4948(3) 0.7846(3) 0.0975(3) 0.0272(11) Uani 1 1 d . . . H28 H 0.4601 0.8043 0.0596 0.033 Uiso 1 1 calc R . . C29 C 0.4729(3) 0.7270(3) 0.1386(2) 0.0244(10) Uani 1 1 d . . . H29 H 0.4230 0.7086 0.1282 0.029 Uiso 1 1 calc R . . C30 C 0.5946(3) 0.8751(3) 0.0672(3) 0.0433(14) Uani 1 1 d . . . H30A H 0.6043 0.8540 0.0227 0.065 Uiso 1 1 calc R . . H30B H 0.6408 0.8975 0.0923 0.065 Uiso 1 1 calc R . . H30C H 0.5555 0.9131 0.0575 0.065 Uiso 1 1 calc R . . C31 C 0.5133(3) 0.7211(3) 0.3597(2) 0.0251(10) Uani 1 1 d . . . H31 H 0.5623 0.7007 0.3699 0.030 Uiso 1 1 calc R . . C32 C 0.4936(3) 0.7783(3) 0.4018(3) 0.0308(11) Uani 1 1 d . . . H32 H 0.5293 0.7958 0.4401 0.037 Uiso 1 1 calc R . . C33 C 0.4213(3) 0.8107(3) 0.3884(3) 0.0286(11) Uani 1 1 d . . . C34 C 0.3708(3) 0.7819(3) 0.3295(2) 0.0258(10) Uani 1 1 d . . . H34 H 0.3218 0.8020 0.3180 0.031 Uiso 1 1 calc R . . C35 C 0.3925(3) 0.7247(3) 0.2890(2) 0.0263(10) Uani 1 1 d . . . H35 H 0.3578 0.7067 0.2503 0.032 Uiso 1 1 calc R . . C36 C 0.3982(3) 0.8730(3) 0.4341(3) 0.0432(14) Uani 1 1 d . . . H36A H 0.3571 0.9015 0.4070 0.065 Uiso 1 1 calc R . . H36B H 0.4411 0.9057 0.4490 0.065 Uiso 1 1 calc R . . H36C H 0.3815 0.8516 0.4756 0.065 Uiso 1 1 calc R . . C37 C 0.6056(3) 0.5534(3) 0.2436(2) 0.0262(10) Uani 1 1 d . . . H37 H 0.6106 0.5755 0.1999 0.031 Uiso 1 1 calc R . . C38 C 0.6493(3) 0.4918(3) 0.2669(3) 0.0307(11) Uani 1 1 d . . . H38 H 0.6838 0.4728 0.2393 0.037 Uiso 1 1 calc R . . C39 C 0.6425(3) 0.4571(3) 0.3318(3) 0.0340(12) Uani 1 1 d . . . C40 C 0.5900(3) 0.4880(3) 0.3709(3) 0.0327(12) Uani 1 1 d . . . H40 H 0.5839 0.4663 0.4144 0.039 Uiso 1 1 calc R . . C41 C 0.5473(3) 0.5500(3) 0.3460(3) 0.0288(11) Uani 1 1 d . . . H41 H 0.5124 0.5697 0.3729 0.035 Uiso 1 1 calc R . . C42 C 0.6895(4) 0.3888(3) 0.3578(3) 0.0450(15) Uani 1 1 d . . . H42A H 0.6995 0.3885 0.4093 0.068 Uiso 1 1 calc R . . H42B H 0.7371 0.3903 0.3398 0.068 Uiso 1 1 calc R . . H42C H 0.6619 0.3438 0.3407 0.068 Uiso 1 1 calc R . . C43 C 0.4347(3) 0.5571(3) 0.1430(2) 0.0268(10) Uani 1 1 d . . . H43 H 0.4698 0.5786 0.1173 0.032 Uiso 1 1 calc R . . C44 C 0.3917(3) 0.4970(3) 0.1140(3) 0.0323(12) Uani 1 1 d . . . H44 H 0.3971 0.4789 0.0689 0.039 Uiso 1 1 calc R . . C45 C 0.3397(3) 0.4628(3) 0.1519(3) 0.0318(11) Uani 1 1 d . . . C46 C 0.3330(3) 0.4929(3) 0.2187(3) 0.0307(11) Uani 1 1 d . . . H46 H 0.2988 0.4716 0.2454 0.037 Uiso 1 1 calc R . . C47 C 0.3765(3) 0.5537(3) 0.2451(2) 0.0237(10) Uani 1 1 d . . . H47 H 0.3708 0.5734 0.2896 0.028 Uiso 1 1 calc R . . C48 C 0.2939(4) 0.3951(3) 0.1224(3) 0.0463(15) Uani 1 1 d . . . H48A H 0.2832 0.3983 0.0710 0.069 Uiso 1 1 calc R . . H48B H 0.2467 0.3938 0.1410 0.069 Uiso 1 1 calc R . . H48C H 0.3227 0.3499 0.1364 0.069 Uiso 1 1 calc R . . B1 B 0.9950(3) 0.5729(3) 0.2467(3) 0.0232(11) Uani 1 1 d . . . B2 B 0.4915(3) 0.6395(3) 0.2471(3) 0.0235(11) Uani 1 1 d . . . N1 N 1.0287(2) 0.5272(2) 0.1882(2) 0.0226(8) Uani 1 1 d . . . N2 N 1.0587(2) 0.6206(2) 0.2944(2) 0.0230(8) Uani 1 1 d . . . N3 N 0.9603(2) 0.5217(2) 0.3007(2) 0.0250(9) Uani 1 1 d . . . N4 N 0.9304(2) 0.6228(2) 0.2028(2) 0.0222(8) Uani 1 1 d . . . N5 N 0.5220(2) 0.6962(2) 0.19389(19) 0.0215(8) Uani 1 1 d . . . N6 N 0.4631(2) 0.6933(2) 0.30333(19) 0.0211(8) Uani 1 1 d . . . N7 N 0.4279(2) 0.5864(2) 0.20818(19) 0.0222(8) Uani 1 1 d . . . N8 N 0.5548(2) 0.5832(2) 0.2828(2) 0.0227(8) Uani 1 1 d . . . Br1 Br 0.39076(3) 0.58995(3) 0.44233(2) 0.02755(13) Uani 1 1 d . . . Br2 Br 0.59878(3) 0.60053(3) 0.05658(2) 0.02760(13) Uani 1 1 d . . . Br3 Br 1.18667(3) 0.89614(3) 0.29972(3) 0.03689(15) Uani 1 1 d . . . Br4 Br 0.25896(3) 0.67728(3) 0.12184(3) 0.04079(16) Uani 1 1 d . . . Br5 Br 1.17130(3) 0.38783(3) 0.27856(3) 0.04463(18) Uani 1 1 d . . . Br6 Br 1.28032(4) 0.16692(3) 0.12344(3) 0.04646(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.037(3) 0.021(2) 0.029(3) -0.004(2) 0.013(2) -0.001(2) C2 0.037(3) 0.035(3) 0.024(3) 0.002(2) 0.012(2) -0.004(2) C3 0.035(3) 0.037(3) 0.033(3) -0.009(2) 0.010(2) 0.004(2) C4 0.049(4) 0.048(3) 0.048(4) -0.027(3) 0.018(3) -0.020(3) C5 0.041(3) 0.038(3) 0.051(4) -0.017(3) 0.022(3) -0.015(3) C6 0.042(3) 0.057(4) 0.038(3) -0.019(3) 0.013(3) 0.001(3) C7 0.032(3) 0.028(2) 0.032(3) -0.005(2) 0.002(2) 0.008(2) C8 0.032(3) 0.038(3) 0.033(3) 0.001(2) 0.003(2) 0.009(2) C9 0.036(3) 0.028(2) 0.023(3) 0.004(2) 0.007(2) -0.001(2) C10 0.042(3) 0.022(2) 0.030(3) -0.004(2) 0.015(2) 0.000(2) C11 0.030(3) 0.026(2) 0.030(3) -0.005(2) 0.006(2) 0.007(2) C12 0.038(3) 0.039(3) 0.032(3) 0.002(2) 0.003(2) -0.002(2) C13 0.045(3) 0.042(3) 0.048(3) 0.018(3) 0.024(3) 0.015(3) C14 0.058(4) 0.038(3) 0.072(5) 0.029(3) 0.039(3) 0.019(3) C15 0.052(4) 0.041(3) 0.048(4) 0.016(3) 0.030(3) 0.012(3) C16 0.046(3) 0.036(3) 0.033(3) 0.007(2) 0.020(2) 0.012(2) C17 0.038(3) 0.025(2) 0.033(3) 0.001(2) 0.018(2) 0.001(2) C18 0.072(5) 0.077(5) 0.084(5) 0.052(4) 0.055(4) 0.036(4) C19 0.031(3) 0.031(3) 0.040(3) 0.011(2) 0.006(2) -0.002(2) C20 0.029(3) 0.035(3) 0.042(3) 0.005(2) 0.006(2) -0.008(2) C21 0.035(3) 0.027(2) 0.020(2) 0.0005(19) 0.006(2) 0.005(2) C22 0.035(3) 0.022(2) 0.031(3) 0.004(2) 0.009(2) -0.002(2) C23 0.026(3) 0.022(2) 0.029(3) -0.002(2) 0.009(2) -0.002(2) C24 0.039(3) 0.037(3) 0.036(3) 0.008(2) 0.003(2) -0.001(2) C25 0.029(3) 0.023(2) 0.022(2) 0.0024(19) 0.0041(19) 0.000(2) C26 0.026(3) 0.027(2) 0.029(3) 0.000(2) 0.006(2) -0.001(2) C27 0.037(3) 0.020(2) 0.027(3) 0.0038(19) 0.015(2) 0.000(2) C28 0.031(3) 0.024(2) 0.027(3) 0.006(2) 0.006(2) 0.004(2) C29 0.026(3) 0.024(2) 0.024(2) -0.0022(19) 0.0072(19) -0.002(2) C30 0.042(3) 0.037(3) 0.052(4) 0.020(3) 0.010(3) -0.004(3) C31 0.027(3) 0.024(2) 0.024(2) -0.0004(19) 0.004(2) 0.002(2) C32 0.033(3) 0.033(3) 0.025(3) -0.006(2) 0.004(2) 0.002(2) C33 0.037(3) 0.025(2) 0.024(3) -0.006(2) 0.008(2) 0.002(2) C34 0.026(3) 0.025(2) 0.027(3) 0.0013(19) 0.005(2) 0.004(2) C35 0.027(3) 0.031(3) 0.021(2) 0.0007(19) 0.0030(19) 0.000(2) C36 0.045(4) 0.039(3) 0.044(3) -0.017(3) 0.005(3) 0.007(3) C37 0.035(3) 0.027(2) 0.021(2) -0.0009(19) 0.015(2) 0.000(2) C38 0.031(3) 0.028(3) 0.037(3) 0.000(2) 0.018(2) 0.002(2) C39 0.039(3) 0.026(3) 0.041(3) 0.005(2) 0.017(2) 0.005(2) C40 0.041(3) 0.032(3) 0.029(3) 0.013(2) 0.019(2) 0.007(2) C41 0.037(3) 0.027(2) 0.026(3) 0.003(2) 0.017(2) 0.004(2) C42 0.054(4) 0.031(3) 0.057(4) 0.017(3) 0.027(3) 0.019(3) C43 0.038(3) 0.025(2) 0.020(2) -0.0011(19) 0.013(2) -0.003(2) C44 0.037(3) 0.033(3) 0.030(3) -0.009(2) 0.016(2) -0.005(2) C45 0.033(3) 0.027(3) 0.037(3) -0.002(2) 0.012(2) -0.004(2) C46 0.036(3) 0.028(3) 0.031(3) 0.000(2) 0.017(2) -0.006(2) C47 0.031(3) 0.024(2) 0.018(2) -0.0001(18) 0.0099(19) 0.001(2) C48 0.053(4) 0.040(3) 0.050(4) -0.016(3) 0.020(3) -0.019(3) B1 0.026(3) 0.019(3) 0.027(3) 0.003(2) 0.011(2) 0.001(2) B2 0.032(3) 0.021(3) 0.020(3) -0.001(2) 0.012(2) 0.000(2) N1 0.024(2) 0.0186(18) 0.026(2) -0.0014(15) 0.0057(16) -0.0036(16) N2 0.027(2) 0.0208(19) 0.021(2) 0.0009(15) 0.0058(16) 0.0015(16) N3 0.030(2) 0.0196(19) 0.028(2) 0.0052(16) 0.0116(17) 0.0015(16) N4 0.024(2) 0.0204(19) 0.024(2) 0.0021(15) 0.0098(16) -0.0002(16) N5 0.026(2) 0.0205(19) 0.0185(19) 0.0003(15) 0.0060(16) 0.0010(16) N6 0.024(2) 0.0212(19) 0.0187(19) 0.0015(15) 0.0061(15) 0.0012(16) N7 0.029(2) 0.0205(19) 0.019(2) -0.0002(15) 0.0088(16) -0.0014(16) N8 0.030(2) 0.0211(19) 0.019(2) 0.0021(15) 0.0113(16) 0.0028(16) Br1 0.0321(3) 0.0305(3) 0.0210(2) 0.00099(18) 0.00717(19) 0.0027(2) Br2 0.0311(3) 0.0329(3) 0.0201(2) -0.00226(19) 0.00796(19) -0.0045(2) Br3 0.0325(3) 0.0286(3) 0.0536(3) 0.0095(2) 0.0189(2) 0.0076(2) Br4 0.0418(3) 0.0383(3) 0.0395(3) 0.0017(2) -0.0012(2) -0.0076(2) Br5 0.0448(3) 0.0318(3) 0.0650(4) 0.0128(3) 0.0316(3) 0.0092(2) Br6 0.0541(4) 0.0392(3) 0.0418(4) 0.0012(2) -0.0043(3) -0.0046(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 C1 N1 1.343(6) . ? C1 C2 1.376(7) . ? C1 H1 0.9300 . ? C2 C3 1.388(7) . ? C2 H2 0.9300 . ? C3 C4 1.370(8) . ? C3 C6 1.494(7) . ? C4 C5 1.375(7) . ? C4 H4 0.9300 . ? C5 N1 1.361(6) . ? C5 H5 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N2 1.349(6) . ? C7 C8 1.367(7) . ? C7 H7 0.9300 . ? C8 C9 1.395(7) . ? C8 H8 0.9300 . ? C9 C10 1.392(7) . ? C9 C12 1.482(7) . ? C10 C11 1.378(7) . ? C10 H10 0.9300 . ? C11 N2 1.351(6) . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N3 1.354(6) . ? C13 C14 1.374(7) . ? C13 H13 0.9300 . ? C14 C15 1.390(8) . ? C14 H14 0.9300 . ? C15 C16 1.379(7) . ? C15 C18 1.489(7) . ? C16 C17 1.376(7) . ? C16 H16 0.9300 . ? C17 N3 1.346(6) . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N4 1.352(6) . ? C19 C20 1.372(7) . ? C19 H19 0.9300 . ? C20 C21 1.399(7) . ? C20 H20 0.9300 . ? C21 C22 1.386(7) . ? C21 C24 1.482(7) . ? C22 C23 1.364(7) . ? C22 H22 0.9300 . ? C23 N4 1.354(6) . ? C23 H23 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 N5 1.348(6) . ? C25 C26 1.372(6) . ? C25 H25 0.9300 . ? C26 C27 1.404(7) . ? C26 H26 0.9300 . ? C27 C28 1.387(7) . ? C27 C30 1.503(6) . ? C28 C29 1.374(6) . ? C28 H28 0.9300 . ? C29 N5 1.356(6) . ? C29 H29 0.9300 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 N6 1.359(6) . ? C31 C32 1.366(6) . ? C31 H31 0.9300 . ? C32 C33 1.386(7) . ? C32 H32 0.9300 . ? C33 C34 1.401(7) . ? C33 C36 1.497(7) . ? C34 C35 1.360(6) . ? C34 H34 0.9300 . ? C35 N6 1.353(6) . ? C35 H35 0.9300 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 N8 1.363(5) . ? C37 C38 1.364(7) . ? C37 H37 0.9300 . ? C38 C39 1.394(7) . ? C38 H38 0.9300 . ? C39 C40 1.390(7) . ? C39 C42 1.501(7) . ? C40 C41 1.369(7) . ? C40 H40 0.9300 . ? C41 N8 1.356(6) . ? C41 H41 0.9300 . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C43 N7 1.360(6) . ? C43 C44 1.367(7) . ? C43 H43 0.9300 . ? C44 C45 1.395(7) . ? C44 H44 0.9300 . ? C45 C46 1.393(7) . ? C45 C48 1.497(7) . ? C46 C47 1.366(7) . ? C46 H46 0.9300 . ? C47 N7 1.364(5) . ? C47 H47 0.9300 . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 0.9600 . ? B1 N1 1.564(6) . ? B1 N3 1.562(6) . ? B1 N4 1.569(6) . ? B1 N2 1.567(7) . ? B2 N7 1.554(7) . ? B2 N8 1.564(7) . ? B2 N6 1.569(6) . ? B2 N5 1.578(6) . ? 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 C1 C2 122.6(4) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 120.3(5) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 116.5(5) . . ? C4 C3 C6 121.2(5) . . ? C2 C3 C6 122.2(5) . . ? C3 C4 C5 121.7(5) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? N1 C5 C4 121.2(5) . . ? N1 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 C8 121.0(4) . . ? N2 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C7 C8 C9 121.5(5) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C10 C9 C8 116.0(5) . . ? C10 C9 C12 121.8(4) . . ? C8 C9 C12 122.2(5) . . ? C11 C10 C9 121.1(4) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? N2 C11 C10 120.9(4) . . ? N2 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 C14 121.4(5) . . ? N3 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C13 C14 C15 120.6(5) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 117.6(5) . . ? C16 C15 C18 121.4(5) . . ? C14 C15 C18 121.0(5) . . ? C15 C16 C17 119.5(5) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? N3 C17 C16 122.9(5) . . ? N3 C17 H17 118.5 . . ? C16 C17 H17 118.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N4 C19 C20 121.9(4) . . ? N4 C19 H19 119.1 . . ? C20 C19 H19 119.1 . . ? C19 C20 C21 120.6(5) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C22 C21 C20 116.1(4) . . ? C22 C21 C24 122.6(4) . . ? C20 C21 C24 121.3(5) . . ? C23 C22 C21 121.6(4) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? N4 C23 C22 121.6(4) . . ? N4 C23 H23 119.2 . . ? C22 C23 H23 119.2 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N5 C25 C26 122.1(4) . . ? N5 C25 H25 118.9 . . ? C26 C25 H25 118.9 . . ? C25 C26 C27 119.7(4) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C28 C27 C26 117.5(4) . . ? C28 C27 C30 121.3(5) . . ? C26 C27 C30 121.3(5) . . ? C29 C28 C27 120.2(5) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? N5 C29 C28 121.7(4) . . ? N5 C29 H29 119.1 . . ? C28 C29 H29 119.1 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N6 C31 C32 121.8(4) . . ? N6 C31 H31 119.1 . . ? C32 C31 H31 119.1 . . ? C31 C32 C33 121.1(5) . . ? C31 C32 H32 119.5 . . ? C33 C32 H32 119.5 . . ? C32 C33 C34 116.2(4) . . ? C32 C33 C36 122.0(5) . . ? C34 C33 C36 121.7(5) . . ? C35 C34 C33 120.9(4) . . ? C35 C34 H34 119.5 . . ? C33 C34 H34 119.5 . . ? N6 C35 C34 122.0(4) . . ? N6 C35 H35 119.0 . . ? C34 C35 H35 119.0 . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N8 C37 C38 121.5(4) . . ? N8 C37 H37 119.3 . . ? C38 C37 H37 119.3 . . ? C37 C38 C39 120.5(4) . . ? C37 C38 H38 119.7 . . ? C39 C38 H38 119.7 . . ? C40 C39 C38 117.2(5) . . ? C40 C39 C42 121.7(5) . . ? C38 C39 C42 121.1(5) . . ? C41 C40 C39 120.8(4) . . ? C41 C40 H40 119.6 . . ? C39 C40 H40 119.6 . . ? N8 C41 C40 121.3(4) . . ? N8 C41 H41 119.4 . . ? C40 C41 H41 119.4 . . ? C39 C42 H42A 109.5 . . ? C39 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C39 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? N7 C43 C44 122.0(4) . . ? N7 C43 H43 119.0 . . ? C44 C43 H43 119.0 . . ? C43 C44 C45 120.2(4) . . ? C43 C44 H44 119.9 . . ? C45 C44 H44 119.9 . . ? C44 C45 C46 117.5(5) . . ? C44 C45 C48 121.2(5) . . ? C46 C45 C48 121.3(4) . . ? C47 C46 C45 120.3(4) . . ? C47 C46 H46 119.9 . . ? C45 C46 H46 119.9 . . ? N7 C47 C46 121.9(4) . . ? N7 C47 H47 119.0 . . ? C46 C47 H47 119.0 . . ? C45 C48 H48A 109.5 . . ? C45 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C45 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? N1 B1 N3 113.6(4) . . ? N1 B1 N4 104.3(4) . . ? N3 B1 N4 109.8(4) . . ? N1 B1 N2 111.1(4) . . ? N3 B1 N2 105.1(4) . . ? N4 B1 N2 113.2(4) . . ? N7 B2 N8 103.4(4) . . ? N7 B2 N6 113.4(4) . . ? N8 B2 N6 112.4(4) . . ? N7 B2 N5 112.3(4) . . ? N8 B2 N5 112.5(4) . . ? N6 B2 N5 103.2(4) . . ? C1 N1 C5 117.6(4) . . ? C1 N1 B1 121.7(4) . . ? C5 N1 B1 119.7(4) . . ? C7 N2 C11 119.3(4) . . ? C7 N2 B1 119.0(4) . . ? C11 N2 B1 121.0(4) . . ? C17 N3 C13 118.0(4) . . ? C17 N3 B1 119.8(4) . . ? C13 N3 B1 121.8(4) . . ? C19 N4 C23 118.3(4) . . ? C19 N4 B1 120.8(4) . . ? C23 N4 B1 120.1(4) . . ? C25 N5 C29 118.6(4) . . ? C25 N5 B2 120.1(4) . . ? C29 N5 B2 120.1(4) . . ? C35 N6 C31 118.0(4) . . ? C35 N6 B2 120.2(4) . . ? C31 N6 B2 120.5(4) . . ? C43 N7 C47 118.0(4) . . ? C43 N7 B2 119.4(4) . . ? C47 N7 B2 120.4(4) . . ? C41 N8 C37 118.8(4) . . ? C41 N8 B2 119.1(4) . . ? C37 N8 B2 120.1(4) . . ? 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 N1 C1 C2 C3 0.8(8) . . . . ? C1 C2 C3 C4 1.9(8) . . . . ? C1 C2 C3 C6 -179.6(5) . . . . ? C2 C3 C4 C5 -2.1(9) . . . . ? C6 C3 C4 C5 179.4(6) . . . . ? C3 C4 C5 N1 -0.4(10) . . . . ? N2 C7 C8 C9 1.1(8) . . . . ? C7 C8 C9 C10 2.3(7) . . . . ? C7 C8 C9 C12 -179.9(5) . . . . ? C8 C9 C10 C11 -2.9(7) . . . . ? C12 C9 C10 C11 179.4(5) . . . . ? C9 C10 C11 N2 0.1(7) . . . . ? N3 C13 C14 C15 -0.5(11) . . . . ? C13 C14 C15 C16 2.1(11) . . . . ? C13 C14 C15 C18 -179.9(7) . . . . ? C14 C15 C16 C17 -2.6(9) . . . . ? C18 C15 C16 C17 179.3(7) . . . . ? C15 C16 C17 N3 1.7(9) . . . . ? N4 C19 C20 C21 0.3(8) . . . . ? C19 C20 C21 C22 1.6(7) . . . . ? C19 C20 C21 C24 179.2(5) . . . . ? C20 C21 C22 C23 -1.7(7) . . . . ? C24 C21 C22 C23 -179.4(5) . . . . ? C21 C22 C23 N4 0.0(7) . . . . ? N5 C25 C26 C27 0.3(7) . . . . ? C25 C26 C27 C28 1.9(7) . . . . ? C25 C26 C27 C30 -178.1(5) . . . . ? C26 C27 C28 C29 -1.7(7) . . . . ? C30 C27 C28 C29 178.3(5) . . . . ? C27 C28 C29 N5 -0.7(7) . . . . ? N6 C31 C32 C33 -0.3(7) . . . . ? C31 C32 C33 C34 -0.4(7) . . . . ? C31 C32 C33 C36 179.4(5) . . . . ? C32 C33 C34 C35 0.6(7) . . . . ? C36 C33 C34 C35 -179.3(5) . . . . ? C33 C34 C35 N6 0.0(7) . . . . ? N8 C37 C38 C39 0.6(8) . . . . ? C37 C38 C39 C40 -0.1(8) . . . . ? C37 C38 C39 C42 179.3(5) . . . . ? C38 C39 C40 C41 -0.1(8) . . . . ? C42 C39 C40 C41 -179.5(5) . . . . ? C39 C40 C41 N8 -0.1(8) . . . . ? N7 C43 C44 C45 -1.2(8) . . . . ? C43 C44 C45 C46 1.0(8) . . . . ? C43 C44 C45 C48 -177.8(5) . . . . ? C44 C45 C46 C47 -0.1(8) . . . . ? C48 C45 C46 C47 178.7(5) . . . . ? C45 C46 C47 N7 -0.7(8) . . . . ? C2 C1 N1 C5 -3.3(7) . . . . ? C2 C1 N1 B1 -172.0(5) . . . . ? C4 C5 N1 C1 3.1(8) . . . . ? C4 C5 N1 B1 172.1(5) . . . . ? N3 B1 N1 C1 -150.4(4) . . . . ? N4 B1 N1 C1 90.1(5) . . . . ? N2 B1 N1 C1 -32.2(6) . . . . ? N3 B1 N1 C5 41.1(6) . . . . ? N4 B1 N1 C5 -78.4(5) . . . . ? N2 B1 N1 C5 159.3(4) . . . . ? C8 C7 N2 C11 -4.0(7) . . . . ? C8 C7 N2 B1 -174.7(4) . . . . ? C10 C11 N2 C7 3.5(7) . . . . ? C10 C11 N2 B1 174.0(4) . . . . ? N1 B1 N2 C7 -40.4(5) . . . . ? N3 B1 N2 C7 82.8(5) . . . . ? N4 B1 N2 C7 -157.4(4) . . . . ? N1 B1 N2 C11 149.1(4) . . . . ? N3 B1 N2 C11 -87.7(5) . . . . ? N4 B1 N2 C11 32.1(5) . . . . ? C16 C17 N3 C13 -0.1(8) . . . . ? C16 C17 N3 B1 -172.8(5) . . . . ? C14 C13 N3 C17 -0.6(9) . . . . ? C14 C13 N3 B1 172.0(6) . . . . ? N1 B1 N3 C17 -158.3(4) . . . . ? N4 B1 N3 C17 -42.0(6) . . . . ? N2 B1 N3 C17 80.0(5) . . . . ? N1 B1 N3 C13 29.2(7) . . . . ? N4 B1 N3 C13 145.5(5) . . . . ? N2 B1 N3 C13 -92.4(5) . . . . ? C20 C19 N4 C23 -2.1(7) . . . . ? C20 C19 N4 B1 -171.6(5) . . . . ? C22 C23 N4 C19 1.9(7) . . . . ? C22 C23 N4 B1 171.5(4) . . . . ? N1 B1 N4 C19 88.3(5) . . . . ? N3 B1 N4 C19 -33.8(6) . . . . ? N2 B1 N4 C19 -150.8(4) . . . . ? N1 B1 N4 C23 -81.1(5) . . . . ? N3 B1 N4 C23 156.9(4) . . . . ? N2 B1 N4 C23 39.8(5) . . . . ? C26 C25 N5 C29 -2.6(6) . . . . ? C26 C25 N5 B2 -170.2(4) . . . . ? C28 C29 N5 C25 2.8(6) . . . . ? C28 C29 N5 B2 170.4(4) . . . . ? N7 B2 N5 C25 -155.2(4) . . . . ? N8 B2 N5 C25 -39.0(5) . . . . ? N6 B2 N5 C25 82.3(5) . . . . ? N7 B2 N5 C29 37.5(5) . . . . ? N8 B2 N5 C29 153.6(4) . . . . ? N6 B2 N5 C29 -85.0(5) . . . . ? C34 C35 N6 C31 -0.7(6) . . . . ? C34 C35 N6 B2 -167.8(4) . . . . ? C32 C31 N6 C35 0.9(6) . . . . ? C32 C31 N6 B2 167.9(4) . . . . ? N7 B2 N6 C35 -38.6(6) . . . . ? N8 B2 N6 C35 -155.4(4) . . . . ? N5 B2 N6 C35 83.2(5) . . . . ? N7 B2 N6 C31 154.7(4) . . . . ? N8 B2 N6 C31 37.9(6) . . . . ? N5 B2 N6 C31 -83.5(5) . . . . ? C44 C43 N7 C47 0.4(7) . . . . ? C44 C43 N7 B2 164.0(5) . . . . ? C46 C47 N7 C43 0.5(7) . . . . ? C46 C47 N7 B2 -162.9(5) . . . . ? N8 B2 N7 C43 -81.1(5) . . . . ? N6 B2 N7 C43 156.9(4) . . . . ? N5 B2 N7 C43 40.4(6) . . . . ? N8 B2 N7 C47 82.1(5) . . . . ? N6 B2 N7 C47 -39.9(6) . . . . ? N5 B2 N7 C47 -156.5(4) . . . . ? C40 C41 N8 C37 0.5(7) . . . . ? C40 C41 N8 B2 164.4(5) . . . . ? C38 C37 N8 C41 -0.8(7) . . . . ? C38 C37 N8 B2 -164.4(5) . . . . ? N7 B2 N8 C41 -81.4(5) . . . . ? N6 B2 N8 C41 41.2(6) . . . . ? N5 B2 N8 C41 157.2(4) . . . . ? N7 B2 N8 C37 82.2(5) . . . . ? N6 B2 N8 C37 -155.2(4) . . . . ? N5 B2 N8 C37 -39.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 4.523 _refine_diff_density_min -2.517 _refine_diff_density_rms 0.132