data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Metzler-Nolte, Nils' _publ_contact_author_email metzler-nolte@rub.de _publ_section_title ; Microwave-assisted Synthesis of the Tp Sandwich Compound TpRu(p-Br-C6H4Tp) and Application of its Benzoic Acid Derivative TpRu(p-(CO2H)-C6H4Tp) in the Covalent Labelling of Biomolecules ; loop_ _publ_author_name N.Metzler-Nolte J.Zagermann data_jz33sad _database_code_depnum_ccdc_archive 'CCDC 781625' #TrackingRef 'jz33sad.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _space_group_name_Hall '-P 2ybc' _chemical_formula_moiety 'C24 H23 B2 Br N12 Ru' _chemical_formula_sum 'C24 H23 B2 Br N12 Ru' _chemical_formula_weight 682.14 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' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 9.1476(2) _cell_length_b 17.3437(3) _cell_length_c 17.1771(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.939(2) _cell_angle_gamma 90.00 _cell_volume 2684.30(9) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 500 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 25.00 _exptl_crystal_description cubic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.688 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 2.113 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6773 _exptl_absorpt_correction_T_max 0.8165 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Sapphire2-CCD, Oxford Diffraction' _diffrn_measurement_method '560 images at 1.0 deg. in \w and 25 sec.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9542 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4723 _reflns_number_gt 3912 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD 1.171.13, Oxford Diffraction' _computing_cell_refinement 'CrysAlis RED 1.171.13, Oxford Diffraction' _computing_data_reduction 'CrysAlis RED 1.171.13, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.0370P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4723 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0292 _refine_ls_R_factor_gt 0.0232 _refine_ls_wR_factor_ref 0.0565 _refine_ls_wR_factor_gt 0.0556 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _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 Ru1 Ru 0.907199(19) 0.168825(10) 0.379666(10) 0.01309(6) Uani 1 1 d . . . Br1 Br 0.39954(3) 0.506099(14) 0.674099(14) 0.02388(8) Uani 1 1 d . . . N9 N 0.8369(2) 0.15977(10) 0.48590(11) 0.0154(4) Uani 1 1 d . . . N8 N 0.8714(2) 0.32800(10) 0.44066(11) 0.0142(4) Uani 1 1 d . . . N11 N 0.6979(2) 0.21043(10) 0.33630(11) 0.0155(4) Uani 1 1 d . . . N4 N 1.1198(2) 0.12868(11) 0.41962(11) 0.0172(4) Uani 1 1 d . . . N2 N 0.9730(2) 0.18099(10) 0.27116(11) 0.0158(4) Uani 1 1 d . . . N6 N 0.8493(2) 0.05712(10) 0.34797(11) 0.0160(4) Uani 1 1 d . . . N12 N 0.6341(2) 0.26757(10) 0.37488(11) 0.0150(4) Uani 1 1 d . . . N1 N 1.0501(2) 0.12346(11) 0.24251(11) 0.0166(4) Uani 1 1 d . . . N7 N 0.9662(2) 0.28050(10) 0.40931(11) 0.0154(4) Uani 1 1 d . . . N3 N 1.1813(2) 0.07830(10) 0.37302(11) 0.0171(4) Uani 1 1 d . . . N5 N 0.9424(2) 0.01474(10) 0.31019(11) 0.0166(4) Uani 1 1 d . . . C21 C 0.6480(3) 0.44339(12) 0.61636(13) 0.0167(5) Uani 1 1 d . . . H21A H 0.7058 0.4737 0.6563 0.020 Uiso 1 1 calc R . . C7 C 0.8839(3) -0.05640(13) 0.29429(13) 0.0186(5) Uani 1 1 d . . . H7A H 0.9271 -0.0967 0.2685 0.022 Uiso 1 1 calc R . . N10 N 0.75473(19) 0.21910(10) 0.50845(10) 0.0133(4) Uani 1 1 d . . . C14 C 0.7605(3) 0.12698(13) 0.59828(14) 0.0196(5) Uani 1 1 d . . . H14A H 0.7453 0.0984 0.6434 0.023 Uiso 1 1 calc R . . C22 C 0.4951(3) 0.44447(12) 0.60639(13) 0.0168(5) Uani 1 1 d . . . C10 C 1.0781(3) 0.32403(13) 0.39493(13) 0.0186(5) Uani 1 1 d . . . H10A H 1.1611 0.3055 0.3740 0.022 Uiso 1 1 calc R . . C12 C 0.9246(3) 0.40087(13) 0.44277(13) 0.0180(5) Uani 1 1 d . . . H12A H 0.8783 0.4450 0.4606 0.022 Uiso 1 1 calc R . . C15 C 0.7083(2) 0.19917(13) 0.57616(13) 0.0173(5) Uani 1 1 d . . . H15A H 0.6490 0.2302 0.6040 0.021 Uiso 1 1 calc R . . C20 C 0.7156(3) 0.39744(12) 0.56720(13) 0.0165(5) Uani 1 1 d . . . H20A H 0.8210 0.3965 0.5746 0.020 Uiso 1 1 calc R . . C8 C 0.7518(3) -0.06060(13) 0.32168(14) 0.0218(5) Uani 1 1 d . . . H8A H 0.6860 -0.1033 0.3187 0.026 Uiso 1 1 calc R . . C23 C 0.4105(3) 0.39947(14) 0.54944(14) 0.0220(5) Uani 1 1 d . . . H23A H 0.3053 0.3999 0.5434 0.026 Uiso 1 1 calc R . . C13 C 0.8410(3) 0.10457(13) 0.54016(13) 0.0182(5) Uani 1 1 d . . . H13A H 0.8915 0.0568 0.5393 0.022 Uiso 1 1 calc R . . C2 C 1.0360(3) 0.21959(14) 0.15681(14) 0.0226(6) Uani 1 1 d . . . H2A H 1.0463 0.2503 0.1122 0.027 Uiso 1 1 calc R . . C9 C 0.7354(3) 0.01147(13) 0.35475(14) 0.0192(5) Uani 1 1 d . . . H9A H 0.6537 0.0261 0.3789 0.023 Uiso 1 1 calc R . . C3 C 0.9636(3) 0.23888(13) 0.21920(13) 0.0193(5) Uani 1 1 d . . . H3A H 0.9145 0.2865 0.2241 0.023 Uiso 1 1 calc R . . C18 C 0.5070(2) 0.28973(13) 0.32885(14) 0.0189(5) Uani 1 1 d . . . H18A H 0.4432 0.3294 0.3412 0.023 Uiso 1 1 calc R . . C19 C 0.6354(2) 0.35213(12) 0.50682(13) 0.0154(5) Uani 1 1 d . . . C17 C 0.4841(3) 0.24588(13) 0.26106(14) 0.0227(6) Uani 1 1 d . . . H17A H 0.4028 0.2485 0.2184 0.027 Uiso 1 1 calc R . . C11 C 1.0567(3) 0.40056(13) 0.41483(14) 0.0207(5) Uani 1 1 d . . . H11A H 1.1196 0.4433 0.4101 0.025 Uiso 1 1 calc R . . B2 B 0.7206(3) 0.29364(15) 0.45738(15) 0.0159(5) Uani 1 1 d . . . C5 C 1.3594(3) 0.11013(14) 0.47181(16) 0.0273(6) Uani 1 1 d . . . H5A H 1.4523 0.1133 0.5063 0.033 Uiso 1 1 calc R . . C24 C 0.4809(3) 0.35354(14) 0.50101(14) 0.0207(5) Uani 1 1 d . . . H24A H 0.4222 0.3220 0.4626 0.025 Uiso 1 1 calc R . . C1 C 1.0895(3) 0.14625(14) 0.17414(13) 0.0204(5) Uani 1 1 d . . . H1A H 1.1450 0.1166 0.1430 0.025 Uiso 1 1 calc R . . C4 C 1.3254(3) 0.06784(14) 0.40357(15) 0.0223(5) Uani 1 1 d . . . H4A H 1.3927 0.0363 0.3815 0.027 Uiso 1 1 calc R . . C6 C 1.2278(3) 0.14731(14) 0.47931(14) 0.0230(6) Uani 1 1 d . . . H6A H 1.2164 0.1813 0.5212 0.028 Uiso 1 1 calc R . . B1 B 1.0882(3) 0.05087(15) 0.29410(16) 0.0185(6) Uani 1 1 d . . . H1 H 1.1454 0.0131 0.2672 0.022 Uiso 1 1 calc R . . C16 C 0.6063(3) 0.19687(13) 0.26875(14) 0.0205(5) Uani 1 1 d . . . H16A H 0.6219 0.1590 0.2310 0.025 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ru1 0.01214(10) 0.01355(10) 0.01289(10) 0.00027(7) 0.00022(7) 0.00031(7) Br1 0.02311(15) 0.02662(15) 0.02332(14) -0.00307(10) 0.00797(10) 0.00444(10) N9 0.0140(10) 0.0151(10) 0.0162(10) -0.0011(8) 0.0001(8) -0.0002(8) N8 0.0141(10) 0.0131(10) 0.0147(9) 0.0000(8) 0.0008(8) 0.0009(8) N11 0.0152(10) 0.0138(10) 0.0167(10) -0.0017(8) 0.0010(8) 0.0000(8) N4 0.0165(10) 0.0181(10) 0.0165(10) 0.0029(8) 0.0017(8) 0.0015(8) N2 0.0152(10) 0.0157(10) 0.0151(10) 0.0009(8) -0.0010(8) 0.0011(8) N6 0.0132(10) 0.0184(10) 0.0160(10) -0.0006(8) 0.0015(8) 0.0015(8) N12 0.0146(10) 0.0135(10) 0.0160(10) -0.0012(8) -0.0001(8) 0.0008(8) N1 0.0151(10) 0.0189(10) 0.0159(10) 0.0010(8) 0.0026(8) 0.0040(8) N7 0.0123(10) 0.0182(10) 0.0151(10) 0.0005(8) 0.0008(8) -0.0005(8) N3 0.0158(10) 0.0170(10) 0.0187(10) 0.0030(8) 0.0036(8) 0.0030(8) N5 0.0172(10) 0.0167(10) 0.0161(10) 0.0008(8) 0.0034(8) 0.0061(8) C21 0.0207(13) 0.0142(12) 0.0146(11) 0.0021(9) 0.0017(9) -0.0030(10) C7 0.0236(13) 0.0137(12) 0.0165(12) -0.0021(10) -0.0023(10) 0.0020(10) N10 0.0121(10) 0.0140(10) 0.0130(9) -0.0027(8) -0.0001(7) -0.0013(8) C14 0.0234(13) 0.0197(13) 0.0145(11) 0.0011(10) 0.0000(10) -0.0050(10) C22 0.0215(13) 0.0152(12) 0.0145(12) 0.0033(9) 0.0047(10) 0.0044(10) C10 0.0128(12) 0.0237(13) 0.0185(12) 0.0016(10) 0.0004(9) -0.0028(10) C12 0.0229(13) 0.0135(12) 0.0159(12) -0.0008(10) -0.0015(10) -0.0012(10) C15 0.0160(12) 0.0209(12) 0.0146(12) -0.0034(10) 0.0017(9) -0.0058(10) C20 0.0141(12) 0.0155(12) 0.0193(12) 0.0030(10) 0.0010(9) 0.0000(9) C8 0.0212(14) 0.0171(12) 0.0252(13) -0.0008(10) -0.0014(10) -0.0031(10) C23 0.0127(12) 0.0338(14) 0.0194(13) 0.0009(11) 0.0024(10) 0.0001(10) C13 0.0192(13) 0.0145(12) 0.0193(12) 0.0018(10) -0.0009(10) -0.0008(10) C2 0.0215(13) 0.0267(14) 0.0188(13) 0.0076(11) 0.0009(10) -0.0032(11) C9 0.0139(12) 0.0215(13) 0.0220(13) -0.0003(10) 0.0028(10) -0.0012(10) C3 0.0181(13) 0.0189(12) 0.0183(12) 0.0031(10) -0.0041(10) -0.0015(10) C18 0.0158(12) 0.0187(12) 0.0210(12) 0.0009(10) 0.0000(10) 0.0039(10) C19 0.0177(12) 0.0135(11) 0.0145(11) 0.0029(9) 0.0013(9) -0.0007(9) C17 0.0201(13) 0.0252(13) 0.0191(13) -0.0026(11) -0.0073(10) 0.0029(11) C11 0.0198(13) 0.0202(13) 0.0211(13) 0.0012(10) 0.0006(10) -0.0084(10) B2 0.0148(14) 0.0163(13) 0.0155(13) -0.0005(11) -0.0005(10) -0.0015(11) C5 0.0155(13) 0.0289(14) 0.0340(15) 0.0024(12) -0.0061(11) -0.0005(11) C24 0.0186(13) 0.0265(14) 0.0159(12) -0.0038(10) -0.0002(10) -0.0054(10) C1 0.0152(12) 0.0301(14) 0.0161(12) 0.0014(10) 0.0031(10) 0.0009(10) C4 0.0121(12) 0.0213(13) 0.0329(14) 0.0035(11) 0.0023(10) 0.0030(10) C6 0.0205(13) 0.0242(13) 0.0218(13) -0.0014(11) -0.0034(10) -0.0037(10) B1 0.0193(14) 0.0182(14) 0.0183(14) -0.0004(11) 0.0041(11) 0.0032(11) C16 0.0231(14) 0.0190(12) 0.0177(12) -0.0047(10) -0.0010(10) 0.0007(10) _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 Ru1 N9 2.0430(18) . ? Ru1 N7 2.0510(18) . ? Ru1 N6 2.0569(18) . ? Ru1 N11 2.0611(18) . ? Ru1 N2 2.0658(19) . ? Ru1 N4 2.0684(19) . ? Br1 C22 1.900(2) . ? N9 C13 1.332(3) . ? N9 N10 1.369(2) . ? N8 C12 1.352(3) . ? N8 N7 1.372(2) . ? N8 B2 1.574(3) . ? N11 C16 1.330(3) . ? N11 N12 1.377(3) . ? N4 C6 1.335(3) . ? N4 N3 1.369(3) . ? N2 C3 1.336(3) . ? N2 N1 1.362(3) . ? N6 C9 1.330(3) . ? N6 N5 1.371(2) . ? N12 C18 1.344(3) . ? N12 B2 1.566(3) . ? N1 C1 1.346(3) . ? N1 B1 1.545(3) . ? N7 C10 1.329(3) . ? N3 C4 1.344(3) . ? N3 B1 1.546(3) . ? N5 C7 1.354(3) . ? N5 B1 1.541(3) . ? C21 C22 1.380(3) . ? C21 C20 1.383(3) . ? C21 H21A 0.9500 . ? C7 C8 1.373(3) . ? C7 H7A 0.9500 . ? N10 C15 1.350(3) . ? N10 B2 1.563(3) . ? C14 C15 1.370(3) . ? C14 C13 1.394(3) . ? C14 H14A 0.9500 . ? C22 C23 1.380(3) . ? C10 C11 1.393(3) . ? C10 H10A 0.9500 . ? C12 C11 1.375(3) . ? C12 H12A 0.9500 . ? C15 H15A 0.9500 . ? C20 C19 1.403(3) . ? C20 H20A 0.9500 . ? C8 C9 1.392(3) . ? C8 H8A 0.9500 . ? C23 C24 1.388(3) . ? C23 H23A 0.9500 . ? C13 H13A 0.9500 . ? C2 C1 1.377(3) . ? C2 C3 1.395(3) . ? C2 H2A 0.9500 . ? C9 H9A 0.9500 . ? C3 H3A 0.9500 . ? C18 C17 1.376(3) . ? C18 H18A 0.9500 . ? C19 C24 1.399(3) . ? C19 B2 1.608(3) . ? C17 C16 1.392(3) . ? C17 H17A 0.9500 . ? C11 H11A 0.9500 . ? C5 C4 1.372(4) . ? C5 C6 1.391(3) . ? C5 H5A 0.9500 . ? C24 H24A 0.9500 . ? C1 H1A 0.9500 . ? C4 H4A 0.9500 . ? C6 H6A 0.9500 . ? B1 H1 1.0000 . ? C16 H16A 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 N9 Ru1 N7 87.75(7) . . ? N9 Ru1 N6 93.30(7) . . ? N7 Ru1 N6 178.95(7) . . ? N9 Ru1 N11 86.20(7) . . ? N7 Ru1 N11 86.97(7) . . ? N6 Ru1 N11 93.06(7) . . ? N9 Ru1 N2 178.01(7) . . ? N7 Ru1 N2 91.29(7) . . ? N6 Ru1 N2 87.66(7) . . ? N11 Ru1 N2 92.02(7) . . ? N9 Ru1 N4 95.79(7) . . ? N7 Ru1 N4 92.50(7) . . ? N6 Ru1 N4 87.43(7) . . ? N11 Ru1 N4 177.93(7) . . ? N2 Ru1 N4 85.99(7) . . ? C13 N9 N10 107.04(18) . . ? C13 N9 Ru1 134.82(15) . . ? N10 N9 Ru1 117.89(13) . . ? C12 N8 N7 108.85(18) . . ? C12 N8 B2 132.18(19) . . ? N7 N8 B2 118.52(17) . . ? C16 N11 N12 106.94(18) . . ? C16 N11 Ru1 131.29(16) . . ? N12 N11 Ru1 121.50(13) . . ? C6 N4 N3 106.23(19) . . ? C6 N4 Ru1 134.61(17) . . ? N3 N4 Ru1 118.56(14) . . ? C3 N2 N1 106.67(18) . . ? C3 N2 Ru1 133.16(16) . . ? N1 N2 Ru1 120.05(13) . . ? C9 N6 N5 106.43(18) . . ? C9 N6 Ru1 135.04(16) . . ? N5 N6 Ru1 118.53(14) . . ? C18 N12 N11 108.56(18) . . ? C18 N12 B2 134.46(19) . . ? N11 N12 B2 116.97(17) . . ? C1 N1 N2 109.48(18) . . ? C1 N1 B1 132.2(2) . . ? N2 N1 B1 118.01(18) . . ? C10 N7 N8 106.93(18) . . ? C10 N7 Ru1 131.93(16) . . ? N8 N7 Ru1 120.51(13) . . ? C4 N3 N4 109.37(19) . . ? C4 N3 B1 130.9(2) . . ? N4 N3 B1 119.30(18) . . ? C7 N5 N6 109.13(18) . . ? C7 N5 B1 131.20(19) . . ? N6 N5 B1 119.66(18) . . ? C22 C21 C20 118.9(2) . . ? C22 C21 H21A 120.6 . . ? C20 C21 H21A 120.6 . . ? N5 C7 C8 108.7(2) . . ? N5 C7 H7A 125.7 . . ? C8 C7 H7A 125.7 . . ? C15 N10 N9 108.71(18) . . ? C15 N10 B2 129.28(19) . . ? N9 N10 B2 121.94(18) . . ? C15 C14 C13 105.0(2) . . ? C15 C14 H14A 127.5 . . ? C13 C14 H14A 127.5 . . ? C23 C22 C21 120.9(2) . . ? C23 C22 Br1 119.43(17) . . ? C21 C22 Br1 119.68(17) . . ? N7 C10 C11 110.5(2) . . ? N7 C10 H10A 124.8 . . ? C11 C10 H10A 124.8 . . ? N8 C12 C11 108.7(2) . . ? N8 C12 H12A 125.6 . . ? C11 C12 H12A 125.6 . . ? N10 C15 C14 109.1(2) . . ? N10 C15 H15A 125.5 . . ? C14 C15 H15A 125.5 . . ? C21 C20 C19 122.8(2) . . ? C21 C20 H20A 118.6 . . ? C19 C20 H20A 118.6 . . ? C7 C8 C9 104.8(2) . . ? C7 C8 H8A 127.6 . . ? C9 C8 H8A 127.6 . . ? C22 C23 C24 119.2(2) . . ? C22 C23 H23A 120.4 . . ? C24 C23 H23A 120.4 . . ? N9 C13 C14 110.2(2) . . ? N9 C13 H13A 124.9 . . ? C14 C13 H13A 124.9 . . ? C1 C2 C3 104.7(2) . . ? C1 C2 H2A 127.7 . . ? C3 C2 H2A 127.7 . . ? N6 C9 C8 111.0(2) . . ? N6 C9 H9A 124.5 . . ? C8 C9 H9A 124.5 . . ? N2 C3 C2 110.4(2) . . ? N2 C3 H3A 124.8 . . ? C2 C3 H3A 124.8 . . ? N12 C18 C17 109.3(2) . . ? N12 C18 H18A 125.4 . . ? C17 C18 H18A 125.4 . . ? C24 C19 C20 115.8(2) . . ? C24 C19 B2 123.3(2) . . ? C20 C19 B2 120.3(2) . . ? C18 C17 C16 104.7(2) . . ? C18 C17 H17A 127.6 . . ? C16 C17 H17A 127.6 . . ? C12 C11 C10 105.0(2) . . ? C12 C11 H11A 127.5 . . ? C10 C11 H11A 127.5 . . ? N10 B2 N12 106.85(18) . . ? N10 B2 N8 108.61(17) . . ? N12 B2 N8 105.44(18) . . ? N10 B2 C19 107.06(18) . . ? N12 B2 C19 116.41(19) . . ? N8 B2 C19 112.17(18) . . ? C4 C5 C6 104.8(2) . . ? C4 C5 H5A 127.6 . . ? C6 C5 H5A 127.6 . . ? C23 C24 C19 122.3(2) . . ? C23 C24 H24A 118.8 . . ? C19 C24 H24A 118.8 . . ? N1 C1 C2 108.8(2) . . ? N1 C1 H1A 125.6 . . ? C2 C1 H1A 125.6 . . ? N3 C4 C5 108.9(2) . . ? N3 C4 H4A 125.6 . . ? C5 C4 H4A 125.6 . . ? N4 C6 C5 110.7(2) . . ? N4 C6 H6A 124.6 . . ? C5 C6 H6A 124.6 . . ? N5 B1 N1 108.52(18) . . ? N5 B1 N3 109.30(19) . . ? N1 B1 N3 106.73(18) . . ? N5 B1 H1 110.7 . . ? N1 B1 H1 110.7 . . ? N3 B1 H1 110.7 . . ? N11 C16 C17 110.5(2) . . ? N11 C16 H16A 124.8 . . ? C17 C16 H16A 124.8 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.462 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.088