# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_section_title ; Crowded Bis Ligand Complexes of TtzPh,Me with First Row Transition Metals Rearrange due to Ligand Field Effects: Structural and Electronic Characterization (TtzPh,Me = tris(3-phenyl-5-methyl-1,2,4-triazolyl)borate) ; _publ_contact_author_name 'Elizabeth Papish' _publ_contact_author_address ;Department of Chemistry Drexel University 3141 Chestnut St. Philadelphia, PA 19104 ; _publ_contact_author_email elizabeth.papish@drexel.edu _publ_contact_author_phone '(215) 895-2666' loop_ _publ_author_name S.Oseback S.Shim M.Kumar S.Greer S.Gardner K.Lemar ; P.DeGregory ; E.Papish D.Tierney M.Zeller G.Yap data_08mz435_0m _database_code_depnum_ccdc_archive 'CCDC 747505' #TrackingRef '- combined cifs - new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H50 B2 N18 Zn' _chemical_formula_weight 1038.11 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z+1/2' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'y+2/3, x+1/3, -z+5/6' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'y+1/3, x+2/3, -z+7/6' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z-1/2' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-y+2/3, -x+1/3, z-1/6' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-y+1/3, -x+2/3, z+1/6' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' _cell_length_a 13.9305(3) _cell_length_b 13.9305(3) _cell_length_c 43.3326(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7282.5(4) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6575 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 31.11 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3240 _exptl_absorpt_coefficient_mu 0.567 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.776 _exptl_absorpt_correction_T_max 0.868 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 13581 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0132 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -57 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.27 _reflns_number_total 2017 _reflns_number_gt 1841 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART 5.630 (Bruker, 1997-2002)' _computing_cell_refinement 'SAINT+ 6.45 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0476P)^2^+9.8081P] 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 2017 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0834 _refine_ls_wR_factor_gt 0.0806 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.6667 0.3333 0.01090(5) 0.0154(4) Uani 1 3 d S . . H1 H 0.6667 0.3333 -0.0122 0.018 Uiso 1 3 calc SR . . C1 C 0.67957(11) 0.54025(11) -0.02425(3) 0.0215(3) Uani 1 1 d . . . H1A H 0.6539 0.5896 -0.0320 0.032 Uiso 1 1 calc R . . H1B H 0.6505 0.4743 -0.0374 0.032 Uiso 1 1 calc R . . H1C H 0.7608 0.5792 -0.0245 0.032 Uiso 1 1 calc R . . C2 C 0.63940(10) 0.50633(10) 0.00793(3) 0.0171(2) Uani 1 1 d . . . C3 C 0.58074(10) 0.50174(10) 0.05319(3) 0.0161(2) Uani 1 1 d . . . C4 C 0.53414(10) 0.53209(10) 0.07955(3) 0.0171(2) Uani 1 1 d . . . C5 C 0.53737(11) 0.63406(11) 0.07831(3) 0.0222(3) Uani 1 1 d . . . H5 H 0.5669 0.6799 0.0606 0.027 Uiso 1 1 calc R . . C6 C 0.49770(12) 0.66882(12) 0.10274(3) 0.0271(3) Uani 1 1 d . . . H6 H 0.5007 0.7384 0.1018 0.033 Uiso 1 1 calc R . . C7 C 0.45374(12) 0.60190(12) 0.12856(3) 0.0255(3) Uani 1 1 d . . . H7 H 0.4278 0.6263 0.1454 0.031 Uiso 1 1 calc R . . C8 C 0.44754(11) 0.49926(12) 0.12977(3) 0.0221(3) Uani 1 1 d . . . H8 H 0.4161 0.4529 0.1473 0.027 Uiso 1 1 calc R . . C9 C 0.48735(10) 0.46425(11) 0.10531(3) 0.0190(3) Uani 1 1 d . . . H9 H 0.4826 0.3939 0.1062 0.023 Uiso 1 1 calc R . . N1 N 0.60561(8) 0.41998(8) 0.05278(2) 0.0152(2) Uani 1 1 d . . . N2 N 0.64177(8) 0.42309(9) 0.02291(2) 0.0152(2) Uani 1 1 d . . . N3 N 0.60088(9) 0.55679(9) 0.02598(2) 0.0182(2) Uani 1 1 d . . . Zn1 Zn 0.6667 0.3333 0.0833 0.01391(11) Uani 1 6 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0158(6) 0.0158(6) 0.0145(10) 0.000 0.000 0.0079(3) C1 0.0248(6) 0.0222(6) 0.0188(6) 0.0038(5) 0.0013(5) 0.0129(5) C2 0.0152(5) 0.0164(5) 0.0190(6) 0.0004(4) -0.0027(4) 0.0075(4) C3 0.0137(5) 0.0149(5) 0.0196(6) -0.0011(4) -0.0024(4) 0.0069(4) C4 0.0144(5) 0.0178(6) 0.0204(6) -0.0037(4) -0.0031(4) 0.0090(5) C5 0.0224(6) 0.0199(6) 0.0266(6) -0.0005(5) -0.0003(5) 0.0123(5) C6 0.0268(7) 0.0226(6) 0.0368(8) -0.0056(6) 0.0003(6) 0.0161(6) C7 0.0206(6) 0.0287(7) 0.0293(7) -0.0100(5) 0.0001(5) 0.0139(6) C8 0.0167(6) 0.0268(7) 0.0221(6) -0.0034(5) -0.0004(5) 0.0103(5) C9 0.0166(5) 0.0194(6) 0.0220(6) -0.0023(5) -0.0023(5) 0.0099(5) N1 0.0147(5) 0.0157(5) 0.0148(5) -0.0016(4) 0.0001(4) 0.0073(4) N2 0.0154(5) 0.0158(5) 0.0143(5) 0.0002(4) -0.0003(4) 0.0076(4) N3 0.0174(5) 0.0179(5) 0.0198(5) -0.0001(4) -0.0017(4) 0.0093(4) Zn1 0.01379(13) 0.01379(13) 0.01417(17) 0.000 0.000 0.00689(7) _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 1.5454(13) 2_655 ? B1 N2 1.5454(13) 3_665 ? B1 N2 1.5455(13) . ? B1 H1 1.0000 . ? C1 C2 1.4887(17) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N3 1.3306(16) . ? C2 N2 1.3438(15) . ? C3 N1 1.3462(16) . ? C3 N3 1.3573(16) . ? C3 C4 1.4763(16) . ? C4 C9 1.3955(18) . ? C4 C5 1.3996(18) . ? C5 C6 1.3888(19) . ? C5 H5 0.9500 . ? C6 C7 1.387(2) . ? C6 H6 0.9500 . ? C7 C8 1.390(2) . ? C7 H7 0.9500 . ? C8 C9 1.3925(17) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? N1 N2 1.3817(13) . ? N1 Zn1 2.2270(10) . ? Zn1 N1 2.2268(10) 17_554 ? Zn1 N1 2.2268(10) 18_654 ? Zn1 N1 2.2269(10) 16_544 ? Zn1 N1 2.2271(10) 2_655 ? Zn1 N1 2.2272(10) 3_665 ? 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 N2 109.25(9) 2_655 3_665 ? N2 B1 N2 109.26(9) 2_655 . ? N2 B1 N2 109.26(9) 3_665 . ? N2 B1 H1 109.7 2_655 . ? N2 B1 H1 109.7 3_665 . ? N2 B1 H1 109.7 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N3 C2 N2 111.24(11) . . ? N3 C2 C1 124.73(11) . . ? N2 C2 C1 123.98(11) . . ? N1 C3 N3 113.49(11) . . ? N1 C3 C4 126.05(11) . . ? N3 C3 C4 120.45(11) . . ? C9 C4 C5 119.03(12) . . ? C9 C4 C3 123.25(11) . . ? C5 C4 C3 117.72(11) . . ? C6 C5 C4 120.53(13) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C7 C6 C5 119.97(13) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 120.07(12) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C9 120.07(13) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C4 120.29(12) . . ? C8 C9 H9 119.9 . . ? C4 C9 H9 119.9 . . ? C3 N1 N2 103.29(10) . . ? C3 N1 Zn1 141.30(8) . . ? N2 N1 Zn1 109.98(7) . . ? C2 N2 N1 108.29(10) . . ? C2 N2 B1 130.37(12) . . ? N1 N2 B1 121.07(11) . . ? C2 N3 C3 103.67(10) . . ? N1 Zn1 N1 88.29(4) 17_554 18_654 ? N1 Zn1 N1 88.29(4) 17_554 16_544 ? N1 Zn1 N1 88.29(4) 18_654 16_544 ? N1 Zn1 N1 98.47(5) 17_554 . ? N1 Zn1 N1 85.72(5) 18_654 . ? N1 Zn1 N1 170.82(5) 16_544 . ? N1 Zn1 N1 85.72(5) 17_554 2_655 ? N1 Zn1 N1 170.82(5) 18_654 2_655 ? N1 Zn1 N1 98.47(5) 16_544 2_655 ? N1 Zn1 N1 88.28(4) . 2_655 ? N1 Zn1 N1 170.81(5) 17_554 3_665 ? N1 Zn1 N1 98.47(5) 18_654 3_665 ? N1 Zn1 N1 85.72(5) 16_544 3_665 ? N1 Zn1 N1 88.28(4) . 3_665 ? N1 Zn1 N1 88.27(4) 2_655 3_665 ? 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 C3 C4 C9 -14.57(19) . . . . ? N3 C3 C4 C9 164.33(12) . . . . ? N1 C3 C4 C5 165.59(12) . . . . ? N3 C3 C4 C5 -15.51(17) . . . . ? C9 C4 C5 C6 1.94(19) . . . . ? C3 C4 C5 C6 -178.21(12) . . . . ? C4 C5 C6 C7 -0.4(2) . . . . ? C5 C6 C7 C8 -1.1(2) . . . . ? C6 C7 C8 C9 1.2(2) . . . . ? C7 C8 C9 C4 0.33(19) . . . . ? C5 C4 C9 C8 -1.89(19) . . . . ? C3 C4 C9 C8 178.27(11) . . . . ? N3 C3 N1 N2 -1.25(13) . . . . ? C4 C3 N1 N2 177.72(11) . . . . ? N3 C3 N1 Zn1 147.66(10) . . . . ? C4 C3 N1 Zn1 -33.4(2) . . . . ? N3 C2 N2 N1 -1.65(14) . . . . ? C1 C2 N2 N1 175.83(11) . . . . ? N3 C2 N2 B1 172.21(9) . . . . ? C1 C2 N2 B1 -10.31(19) . . . . ? C3 N1 N2 C2 1.69(12) . . . . ? Zn1 N1 N2 C2 -158.21(8) . . . . ? C3 N1 N2 B1 -172.85(9) . . . . ? Zn1 N1 N2 B1 27.25(11) . . . . ? N2 B1 N2 C2 -132.37(15) 2_655 . . . ? N2 B1 N2 C2 108.15(18) 3_665 . . . ? N2 B1 N2 N1 40.82(15) 2_655 . . . ? N2 B1 N2 N1 -78.66(11) 3_665 . . . ? N2 C2 N3 C3 0.84(13) . . . . ? C1 C2 N3 C3 -176.62(12) . . . . ? N1 C3 N3 C2 0.31(14) . . . . ? C4 C3 N3 C2 -178.73(11) . . . . ? C3 N1 Zn1 N1 68.86(13) . . . 17_554 ? N2 N1 Zn1 N1 -143.47(9) . . . 17_554 ? C3 N1 Zn1 N1 -18.77(11) . . . 18_654 ? N2 N1 Zn1 N1 128.90(9) . . . 18_654 ? C3 N1 Zn1 N1 154.28(14) . . . 2_655 ? N2 N1 Zn1 N1 -58.06(6) . . . 2_655 ? C3 N1 Zn1 N1 -117.40(15) . . . 3_665 ? N2 N1 Zn1 N1 30.27(6) . . . 3_665 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.377 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.052 # Attachment '- combined cifs - new.cif' #TrackingRef '- combined cifs - new.cif' data_lizp026a _database_code_depnum_ccdc_archive 'CCDC 850799' #TrackingRef '- combined cifs - new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C27 H25 B Br N9 Zn), C H4 O' _chemical_formula_sum 'C55 H54 B2 Br2 N18 O Zn2' _chemical_formula_weight 1295.34 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' Zn Zn 0.2839 1.4301 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M P-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' _cell_length_a 10.952(3) _cell_length_b 10.952(3) _cell_length_c 13.883(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1442.1(7) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1017 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 28.10 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 658 _exptl_absorpt_coefficient_mu 2.273 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5373 _exptl_absorpt_correction_T_max 0.7848 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; Data collection is performed with four batch runs at \f = 0.00 \% (600 frames), at \f = 90.00 \% (600 frames), at \f = 180 \% (600 frames) and at \f = 270 \% (600 frames). Frame width = 0.30 \& in \w. Data is merged, corrected for decay, and treated with multi-scan absorption corrections. The H atoms of the methyl group at C9 were disordered as rotationally disordered with H atoms 60 degrees apart. The ccupancy ratio refined to 0.61(2) to 0.39(2). The methanol molecule is disordered across symmetry elements at the origin of the unit cell with the carbon atom localized essentially on the origin. The molecule was refined as disordered over six symmetry equivalent positions and the carbon atom was constrained to have the same ADPs as the oxygen atom. The hydroxyl hydrogen atom position was restrained based on hydrogen bonding position considerations. A slight electron deficiency at the bromine atom, possibly caused by exchange of bromine by chlorine from the methylene chloride solvent, was ignored. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS APEX diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 836.6 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 1 _diffrn_reflns_number 20009 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 28.31 _reflns_number_total 2421 _reflns_number_gt 2169 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2001)' _computing_publication_material 'SHELXTL (Sheldrick, 2001)' _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^)+(0.0390P)^2^+0.6533P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2421 _refine_ls_number_parameters 135 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0316 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0722 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.002 _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 Zn1 Zn 0.6667 0.3333 0.23636(2) 0.01700(9) Uani 1 3 d S . . Br1 Br 0.6667 0.3333 0.399965(19) 0.02789(10) Uani 1 3 d S . . B1 B 0.6667 0.3333 0.0171(2) 0.0180(5) Uani 1 3 d S . . H1 H 0.6667 0.3333 -0.060(2) 0.022 Uiso 1 3 d S . . N1 N 0.50961(13) 0.32761(13) 0.15447(9) 0.0182(3) Uani 1 1 d . . . N2 N 0.53091(13) 0.32724(13) 0.05658(9) 0.0182(3) Uani 1 1 d . . . N3 N 0.32312(14) 0.31037(15) 0.07615(10) 0.0222(3) Uani 1 1 d D . . C1 C 0.17905(18) 0.23335(18) 0.27346(13) 0.0268(3) Uani 1 1 d . . . H1A H 0.1226 0.1633 0.2276 0.032 Uiso 1 1 calc R . . C2 C 0.1192(2) 0.2448(2) 0.35892(14) 0.0329(4) Uani 1 1 d . . . H2A H 0.0222 0.1820 0.3716 0.039 Uiso 1 1 calc R . . C3 C 0.2012(2) 0.3479(2) 0.42565(13) 0.0335(4) Uani 1 1 d . . . H3A H 0.1600 0.3559 0.4838 0.040 Uiso 1 1 calc R . . C4 C 0.3423(2) 0.4389(2) 0.40776(14) 0.0337(4) Uani 1 1 d . . . H4A H 0.3980 0.5096 0.4535 0.040 Uiso 1 1 calc R . . C5 C 0.40356(18) 0.42745(19) 0.32269(13) 0.0278(4) Uani 1 1 d . . . H5A H 0.5010 0.4897 0.3108 0.033 Uiso 1 1 calc R . . C6 C 0.32184(17) 0.32463(17) 0.25509(11) 0.0212(3) Uani 1 1 d . . . C7 C 0.38411(16) 0.31808(16) 0.16250(11) 0.0194(3) Uani 1 1 d . . . C8 C 0.41729(16) 0.31739(16) 0.01213(11) 0.0200(3) Uani 1 1 d . . . C9 C 0.40003(18) 0.31888(17) -0.09385(11) 0.0240(3) Uani 1 1 d . . . H9A H 0.3145 0.3229 -0.1083 0.036 Uiso 0.61(2) 1 calc PR . . H9B H 0.3921 0.2331 -0.1219 0.036 Uiso 0.61(2) 1 calc PR . . H9C H 0.4821 0.4017 -0.1213 0.036 Uiso 0.61(2) 1 calc PR . . H9D H 0.4780 0.3156 -0.1260 0.036 Uiso 0.39(2) 1 calc PR . . H9E H 0.4003 0.4053 -0.1125 0.036 Uiso 0.39(2) 1 calc PR . . H9F H 0.3104 0.2367 -0.1130 0.036 Uiso 0.39(2) 1 calc PR . . O1 O 0.0419(13) 0.0468(12) 0.0853(5) 0.037(2) Uani 0.166666666666 1 d P A -1 H1B H 0.1182 0.1230 0.0790 0.055 Uiso 0.166666666666 1 calc PRD A -1 C10 C -0.014(7) -0.011(12) -0.0089(12) 0.037(2) Uani 0.166666666666 1 d P A -1 H10A H -0.1150 -0.0444 -0.0105 0.055 Uiso 0.166666666666 1 calc PR A -1 H10B H 0.0021 -0.0901 -0.0220 0.055 Uiso 0.166666666666 1 calc PR A -1 H10C H 0.0344 0.0620 -0.0580 0.055 Uiso 0.166666666666 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 Zn1 0.01847(11) 0.01847(11) 0.01406(15) 0.000 0.000 0.00924(6) Br1 0.03413(12) 0.03413(12) 0.01542(14) 0.000 0.000 0.01706(6) B1 0.0178(8) 0.0178(8) 0.0185(14) 0.000 0.000 0.0089(4) N1 0.0200(6) 0.0197(6) 0.0151(6) 0.0000(5) 0.0008(5) 0.0102(5) N2 0.0201(6) 0.0195(6) 0.0152(6) -0.0009(5) -0.0006(5) 0.0101(5) N3 0.0220(6) 0.0238(7) 0.0230(7) -0.0033(5) -0.0033(5) 0.0132(5) C1 0.0255(8) 0.0265(8) 0.0284(9) 0.0019(6) 0.0020(6) 0.0130(7) C2 0.0276(9) 0.0358(10) 0.0344(10) 0.0064(8) 0.0094(7) 0.0152(8) C3 0.0395(10) 0.0439(11) 0.0264(9) 0.0028(8) 0.0088(7) 0.0277(9) C4 0.0367(10) 0.0413(10) 0.0288(9) -0.0090(8) -0.0019(7) 0.0236(9) C5 0.0245(8) 0.0319(9) 0.0287(9) -0.0063(7) -0.0006(7) 0.0152(7) C6 0.0231(7) 0.0228(7) 0.0217(7) 0.0009(6) 0.0010(6) 0.0145(6) C7 0.0198(7) 0.0169(7) 0.0222(7) -0.0011(5) -0.0005(6) 0.0095(6) C8 0.0221(7) 0.0168(7) 0.0219(7) -0.0022(6) -0.0034(6) 0.0104(6) C9 0.0300(8) 0.0226(8) 0.0213(8) -0.0028(6) -0.0067(6) 0.0145(7) O1 0.028(7) 0.035(8) 0.034(4) -0.004(3) -0.001(3) 0.005(3) C10 0.028(7) 0.035(8) 0.034(4) -0.004(3) -0.001(3) 0.005(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 Zn1 N1 2.0364(13) 3_665 ? Zn1 N1 2.0364(13) . ? Zn1 N1 2.0365(13) 2_655 ? Zn1 Br1 2.2713(8) . ? B1 N2 1.5546(16) 3_665 ? B1 N2 1.5546(16) . ? B1 N2 1.5546(16) 2_655 ? B1 H1 1.07(3) . ? N1 C7 1.330(2) . ? N1 N2 1.3793(18) . ? N2 C8 1.344(2) . ? N3 C8 1.334(2) . ? N3 C7 1.354(2) . ? C1 C2 1.391(2) . ? C1 C6 1.395(2) . ? C1 H1A 0.9500 . ? C2 C3 1.388(3) . ? C2 H2A 0.9500 . ? C3 C4 1.380(3) . ? C3 H3A 0.9500 . ? C4 C5 1.394(2) . ? C4 H4A 0.9500 . ? C5 C6 1.394(2) . ? C5 H5A 0.9500 . ? C6 C7 1.474(2) . ? C8 C9 1.485(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C9 H9D 0.9800 . ? C9 H9E 0.9800 . ? C9 H9F 0.9800 . ? O1 C10 1.448(19) . ? O1 H1B 0.8400 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 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 Zn1 N1 91.86(5) 3_665 . ? N1 Zn1 N1 91.87(5) 3_665 2_655 ? N1 Zn1 N1 91.86(5) . 2_655 ? N1 Zn1 Br1 123.94(4) 3_665 . ? N1 Zn1 Br1 123.94(4) . . ? N1 Zn1 Br1 123.93(4) 2_655 . ? N2 B1 N2 108.25(12) 3_665 . ? N2 B1 N2 108.24(12) 3_665 2_655 ? N2 B1 N2 108.25(12) . 2_655 ? N2 B1 H1 110.67(11) 3_665 . ? N2 B1 H1 110.67(11) . . ? N2 B1 H1 110.67(11) 2_655 . ? C7 N1 N2 104.59(12) . . ? C7 N1 Zn1 141.21(11) . . ? N2 N1 Zn1 114.12(9) . . ? C8 N2 N1 107.55(12) . . ? C8 N2 B1 131.95(15) . . ? N1 N2 B1 120.48(15) . . ? C8 N3 C7 104.07(13) . . ? C2 C1 C6 120.07(17) . . ? C2 C1 H1A 120.0 . . ? C6 C1 H1A 120.0 . . ? C3 C2 C1 120.06(17) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C4 C3 C2 120.18(17) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C3 C4 C5 120.20(18) . . ? C3 C4 H4A 119.9 . . ? C5 C4 H4A 119.9 . . ? C6 C5 C4 119.98(17) . . ? C6 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? C5 C6 C1 119.52(15) . . ? C5 C6 C7 120.06(15) . . ? C1 C6 C7 120.32(15) . . ? N1 C7 N3 112.88(14) . . ? N1 C7 C6 123.68(14) . . ? N3 C7 C6 123.33(14) . . ? N3 C8 N2 110.90(14) . . ? N3 C8 C9 124.18(14) . . ? N2 C8 C9 124.89(14) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C9 H9D 109.5 . . ? H9A C9 H9D 141.1 . . ? H9B C9 H9D 56.3 . . ? H9C C9 H9D 56.3 . . ? C8 C9 H9E 109.5 . . ? H9A C9 H9E 56.3 . . ? H9B C9 H9E 141.1 . . ? H9C C9 H9E 56.3 . . ? H9D C9 H9E 109.5 . . ? C8 C9 H9F 109.5 . . ? H9A C9 H9F 56.3 . . ? H9B C9 H9F 56.3 . . ? H9C C9 H9F 141.1 . . ? H9D C9 H9F 109.5 . . ? H9E C9 H9F 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 N1 Zn1 N1 C7 -137.33(19) 3_665 . . . ? N1 Zn1 N1 C7 130.74(19) 2_655 . . . ? Br1 Zn1 N1 C7 -3.30(19) . . . . ? N1 Zn1 N1 N2 46.47(8) 3_665 . . . ? N1 Zn1 N1 N2 -45.46(8) 2_655 . . . ? Br1 Zn1 N1 N2 -179.50(7) . . . . ? C7 N1 N2 C8 -0.07(15) . . . . ? Zn1 N1 N2 C8 177.47(10) . . . . ? C7 N1 N2 B1 -178.49(10) . . . . ? Zn1 N1 N2 B1 -0.95(14) . . . . ? N2 B1 N2 C8 124.1(2) 3_665 . . . ? N2 B1 N2 C8 -118.8(2) 2_655 . . . ? N2 B1 N2 N1 -57.94(16) 3_665 . . . ? N2 B1 N2 N1 59.18(16) 2_655 . . . ? C6 C1 C2 C3 0.6(3) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C4 C5 C6 C1 -0.3(3) . . . . ? C4 C5 C6 C7 176.13(16) . . . . ? C2 C1 C6 C5 -0.3(3) . . . . ? C2 C1 C6 C7 -176.70(16) . . . . ? N2 N1 C7 N3 0.55(17) . . . . ? Zn1 N1 C7 N3 -175.87(12) . . . . ? N2 N1 C7 C6 -175.65(14) . . . . ? Zn1 N1 C7 C6 7.9(3) . . . . ? C8 N3 C7 N1 -0.80(18) . . . . ? C8 N3 C7 C6 175.41(14) . . . . ? C5 C6 C7 N1 45.4(2) . . . . ? C1 C6 C7 N1 -138.23(16) . . . . ? C5 C6 C7 N3 -130.40(17) . . . . ? C1 C6 C7 N3 46.0(2) . . . . ? C7 N3 C8 N2 0.73(17) . . . . ? C7 N3 C8 C9 -177.37(14) . . . . ? N1 N2 C8 N3 -0.43(17) . . . . ? B1 N2 C8 N3 177.74(11) . . . . ? N1 N2 C8 C9 177.66(14) . . . . ? B1 N2 C8 C9 -4.2(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1B N3 0.84 2.15 2.991(8) 173.4 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.496 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.067 data_08mz480_0m _database_code_depnum_ccdc_archive 'CCDC 850800' #TrackingRef '- combined cifs - new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H50 B2 N18 Ni' _chemical_formula_weight 1031.43 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z+1/2' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'y+2/3, x+1/3, -z+5/6' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'y+1/3, x+2/3, -z+7/6' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z-1/2' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-y+2/3, -x+1/3, z-1/6' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-y+1/3, -x+2/3, z+1/6' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' _cell_length_a 13.9385(9) _cell_length_b 13.9385(9) _cell_length_c 43.155(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7261.0(12) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3004 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 30.58 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3228 _exptl_absorpt_coefficient_mu 0.462 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.755 _exptl_absorpt_correction_T_max 0.859 _exptl_absorpt_process_details 'Apex2 v2008.2-4 (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 9297 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -56 _diffrn_reflns_limit_l_max 54 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.27 _reflns_number_total 2004 _reflns_number_gt 1725 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2008.2-4 (Bruker, 2008)' _computing_cell_refinement 'Apex2 v2008.2-4 ' _computing_data_reduction 'Apex2 v2008.2-4 ' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0612P)^2^+10.2712P] 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 2004 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.6667 0.3333 0.01137(7) 0.0167(5) Uani 1 3 d S . . H1 H 0.6667 0.3333 -0.0118 0.020 Uiso 1 3 calc SR . . C1 C 0.67576(13) 0.13822(13) -0.02374(4) 0.0226(3) Uani 1 1 d . . . H1A H 0.7567 0.1832 -0.0245 0.034 Uiso 1 1 calc R . . H1B H 0.6435 0.1719 -0.0370 0.034 Uiso 1 1 calc R . . H1C H 0.6524 0.0632 -0.0311 0.034 Uiso 1 1 calc R . . C2 C 0.63730(12) 0.13279(12) 0.00865(4) 0.0185(3) Uani 1 1 d . . . C3 C 0.58048(12) 0.08090(12) 0.05430(4) 0.0178(3) Uani 1 1 d . . . C4 C 0.53397(12) 0.00432(12) 0.08076(4) 0.0188(3) Uani 1 1 d . . . C5 C 0.53735(13) -0.09440(13) 0.07942(4) 0.0233(3) Uani 1 1 d . . . H5 H 0.5676 -0.1101 0.0617 0.028 Uiso 1 1 calc R . . C6 C 0.49702(14) -0.16923(14) 0.10369(4) 0.0282(4) Uani 1 1 d . . . H6 H 0.5000 -0.2358 0.1026 0.034 Uiso 1 1 calc R . . C7 C 0.45229(14) -0.14720(14) 0.12952(4) 0.0271(4) Uani 1 1 d . . . H7 H 0.4257 -0.1981 0.1463 0.033 Uiso 1 1 calc R . . C8 C 0.44622(13) -0.05083(14) 0.13091(4) 0.0236(3) Uani 1 1 d . . . H8 H 0.4145 -0.0363 0.1485 0.028 Uiso 1 1 calc R . . C9 C 0.48658(12) 0.02443(13) 0.10654(4) 0.0208(3) Uani 1 1 d . . . H9 H 0.4818 0.0900 0.1075 0.025 Uiso 1 1 calc R . . N1 N 0.64168(10) 0.21951(10) 0.02361(3) 0.0167(3) Uani 1 1 d . . . N2 N 0.60702(10) 0.18805(10) 0.05371(3) 0.0166(3) Uani 1 1 d . . . N3 N 0.59884(10) 0.04505(10) 0.02702(3) 0.0192(3) Uani 1 1 d . . . Ni1 Ni 0.6667 0.3333 0.0833 0.01508(15) Uani 1 6 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0161(8) 0.0161(8) 0.0179(13) 0.000 0.000 0.0081(4) C1 0.0247(8) 0.0202(7) 0.0228(8) -0.0031(6) 0.0001(6) 0.0112(6) C2 0.0150(7) 0.0171(7) 0.0236(8) -0.0025(5) -0.0022(5) 0.0082(6) C3 0.0141(6) 0.0157(7) 0.0227(7) -0.0018(5) -0.0030(5) 0.0068(5) C4 0.0152(7) 0.0160(7) 0.0231(8) 0.0002(6) -0.0043(5) 0.0063(6) C5 0.0219(7) 0.0181(7) 0.0294(8) -0.0004(6) -0.0011(6) 0.0097(6) C6 0.0270(8) 0.0181(7) 0.0397(10) 0.0050(7) -0.0004(7) 0.0114(7) C7 0.0205(8) 0.0229(8) 0.0329(9) 0.0101(7) 0.0007(6) 0.0071(6) C8 0.0180(7) 0.0248(8) 0.0242(8) 0.0029(6) 0.0001(6) 0.0077(6) C9 0.0166(7) 0.0170(7) 0.0268(8) 0.0002(6) -0.0030(6) 0.0069(6) N1 0.0153(6) 0.0169(6) 0.0178(6) -0.0005(5) -0.0006(4) 0.0079(5) N2 0.0152(6) 0.0168(6) 0.0176(6) 0.0018(5) 0.0003(4) 0.0078(5) N3 0.0171(6) 0.0172(6) 0.0228(7) -0.0009(5) -0.0020(5) 0.0082(5) Ni1 0.01365(17) 0.01365(17) 0.0179(3) 0.000 0.000 0.00683(9) _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 1.5379(16) . ? B1 N1 1.5379(16) 2_655 ? B1 N1 1.5380(16) 3_665 ? B1 H1 1.0000 . ? C1 C2 1.486(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N3 1.3252(19) . ? C2 N1 1.3444(19) . ? C3 N2 1.3474(19) . ? C3 N3 1.3524(19) . ? C3 C4 1.474(2) . ? C4 C9 1.392(2) . ? C4 C5 1.401(2) . ? C5 C6 1.384(2) . ? C5 H5 0.9500 . ? C6 C7 1.385(3) . ? C6 H6 0.9500 . ? C7 C8 1.389(2) . ? C7 H7 0.9500 . ? C8 C9 1.390(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? N1 N2 1.3788(18) . ? N2 Ni1 2.1777(13) . ? Ni1 N2 2.1777(13) 2_655 ? Ni1 N2 2.1777(13) 3_665 ? Ni1 N2 2.1778(13) 16_544 ? Ni1 N2 2.1778(13) 17_554 ? Ni1 N2 2.1778(13) 18_654 ? 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 N1 108.84(12) . 2_655 ? N1 B1 N1 108.84(12) . 3_665 ? N1 B1 N1 108.84(12) 2_655 3_665 ? N1 B1 H1 110.1 . . ? N1 B1 H1 110.1 2_655 . ? N1 B1 H1 110.1 3_665 . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N3 C2 N1 110.98(13) . . ? N3 C2 C1 125.39(13) . . ? N1 C2 C1 123.58(14) . . ? N2 C3 N3 113.28(13) . . ? N2 C3 C4 126.51(14) . . ? N3 C3 C4 120.19(13) . . ? C9 C4 C5 118.89(14) . . ? C9 C4 C3 123.69(13) . . ? C5 C4 C3 117.42(14) . . ? C6 C5 C4 120.54(16) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 120.05(15) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C6 C7 C8 120.07(15) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C9 119.99(16) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C4 120.42(15) . . ? C8 C9 H9 119.8 . . ? C4 C9 H9 119.8 . . ? C2 N1 N2 108.38(12) . . ? C2 N1 B1 130.36(15) . . ? N2 N1 B1 120.95(14) . . ? C3 N2 N1 103.22(12) . . ? C3 N2 Ni1 141.74(11) . . ? N1 N2 Ni1 110.31(9) . . ? C2 N3 C3 104.11(12) . . ? N2 Ni1 N2 89.04(5) 2_655 3_665 ? N2 Ni1 N2 89.04(5) 2_655 . ? N2 Ni1 N2 89.04(5) 3_665 . ? N2 Ni1 N2 170.46(6) 2_655 16_544 ? N2 Ni1 N2 84.70(6) 3_665 16_544 ? N2 Ni1 N2 98.04(7) . 16_544 ? N2 Ni1 N2 84.70(6) 2_655 17_554 ? N2 Ni1 N2 98.04(7) 3_665 17_554 ? N2 Ni1 N2 170.45(6) . 17_554 ? N2 Ni1 N2 89.04(5) 16_544 17_554 ? N2 Ni1 N2 98.03(7) 2_655 18_654 ? N2 Ni1 N2 170.45(6) 3_665 18_654 ? N2 Ni1 N2 84.70(6) . 18_654 ? N2 Ni1 N2 89.04(5) 16_544 18_654 ? N2 Ni1 N2 89.03(5) 17_554 18_654 ? 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 C3 C4 C9 15.9(2) . . . . ? N3 C3 C4 C9 -162.96(14) . . . . ? N2 C3 C4 C5 -164.72(14) . . . . ? N3 C3 C4 C5 16.4(2) . . . . ? C9 C4 C5 C6 -1.8(2) . . . . ? C3 C4 C5 C6 178.81(14) . . . . ? C4 C5 C6 C7 0.4(2) . . . . ? C5 C6 C7 C8 1.0(3) . . . . ? C6 C7 C8 C9 -0.9(2) . . . . ? C7 C8 C9 C4 -0.5(2) . . . . ? C5 C4 C9 C8 1.8(2) . . . . ? C3 C4 C9 C8 -178.79(14) . . . . ? N3 C2 N1 N2 1.67(16) . . . . ? C1 C2 N1 N2 -175.78(13) . . . . ? N3 C2 N1 B1 -171.82(11) . . . . ? C1 C2 N1 B1 10.7(2) . . . . ? N1 B1 N1 C2 -109.8(2) 2_655 . . . ? N1 B1 N1 C2 131.68(19) 3_665 . . . ? N1 B1 N1 N2 77.38(14) 2_655 . . . ? N1 B1 N1 N2 -41.11(19) 3_665 . . . ? N3 C3 N2 N1 1.52(16) . . . . ? C4 C3 N2 N1 -177.40(13) . . . . ? N3 C3 N2 Ni1 -149.36(13) . . . . ? C4 C3 N2 Ni1 31.7(2) . . . . ? C2 N1 N2 C3 -1.87(15) . . . . ? B1 N1 N2 C3 172.35(11) . . . . ? C2 N1 N2 Ni1 159.39(9) . . . . ? B1 N1 N2 Ni1 -26.39(13) . . . . ? N1 C2 N3 C3 -0.69(16) . . . . ? C1 C2 N3 C3 176.70(14) . . . . ? N2 C3 N3 C2 -0.57(16) . . . . ? C4 C3 N3 C2 178.43(13) . . . . ? C3 N2 Ni1 N2 118.62(18) . . . 2_655 ? N1 N2 Ni1 N2 -31.05(8) . . . 2_655 ? C3 N2 Ni1 N2 -152.33(17) . . . 3_665 ? N1 N2 Ni1 N2 58.01(7) . . . 3_665 ? C3 N2 Ni1 N2 -67.81(15) . . . 16_544 ? N1 N2 Ni1 N2 142.52(10) . . . 16_544 ? C3 N2 Ni1 N2 20.46(13) . . . 18_654 ? N1 N2 Ni1 N2 -129.21(11) . . . 18_654 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.988 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.066 data_09mz030_0m _database_code_depnum_ccdc_archive 'CCDC 850801' #TrackingRef '- combined cifs - new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C54 H50 B2 N18 Ni, C H2 Cl2' _chemical_formula_sum 'C55 H52 B2 Cl2 N18 Ni' _chemical_formula_weight 1116.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 '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 C2/c 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 37.1971(18) _cell_length_b 13.2418(6) _cell_length_c 25.1526(12) _cell_angle_alpha 90.00 _cell_angle_beta 107.4116(7) _cell_angle_gamma 90.00 _cell_volume 11821.4(10) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9381 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 31.35 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4640 _exptl_absorpt_coefficient_mu 0.471 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.713 _exptl_absorpt_correction_T_max 0.797 _exptl_absorpt_process_details 'Apex2 v2008.2-4 (Bruker, 2008)' _exptl_special_details ; Large sections of the structure consist of areas with highly disordered solvate molecules for which no chemically meaningful model could be devised. The data were instead corrected for the electron density in these areas using back-Fourier transform methods (the Squueze method as implemented in Platon, see SQUEEZE report appended to this cif file). ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 45740 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -52 _diffrn_reflns_limit_h_max 53 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 31.47 _reflns_number_total 17863 _reflns_number_gt 13724 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2008.2-4 (Bruker, 2008)' _computing_cell_refinement 'Apex2 v2008.2-4' _computing_data_reduction 'Apex2 v2008.2-4' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^+0.2544P] 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 17863 _refine_ls_number_parameters 710 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1122 _refine_ls_wR_factor_gt 0.1065 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.002 _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 0.30397(4) 0.23807(11) 0.35679(6) 0.0171(3) Uani 1 1 d . . . H1 H 0.2893 0.1778 0.3382 0.020 Uiso 1 1 calc R . . B2 B 0.39366(4) 0.61822(11) 0.47068(6) 0.0151(3) Uani 1 1 d . . . H2 H 0.4072 0.6803 0.4890 0.018 Uiso 1 1 calc R . . C1 C 0.30516(6) 0.03131(12) 0.42055(8) 0.0428(5) Uani 1 1 d . . . H1A H 0.3093 -0.0210 0.4493 0.064 Uiso 1 1 calc R . . H1B H 0.3156 0.0088 0.3911 0.064 Uiso 1 1 calc R . . H1C H 0.2781 0.0435 0.4046 0.064 Uiso 1 1 calc R . . C2 C 0.32416(5) 0.12652(11) 0.44579(6) 0.0261(3) Uani 1 1 d . . . C3 C 0.35488(4) 0.23371(10) 0.50439(6) 0.0208(3) Uani 1 1 d . . . C4 C 0.37676(4) 0.26965(11) 0.56041(6) 0.0217(3) Uani 1 1 d . . . C5 C 0.38429(5) 0.19851(12) 0.60372(7) 0.0342(4) Uani 1 1 d . . . H5 H 0.3744 0.1321 0.5963 0.041 Uiso 1 1 calc R . . C6 C 0.40593(6) 0.22405(13) 0.65709(7) 0.0379(4) Uani 1 1 d . . . H6 H 0.4107 0.1751 0.6860 0.045 Uiso 1 1 calc R . . C7 C 0.42075(5) 0.32089(12) 0.66870(6) 0.0294(3) Uani 1 1 d . . . H7 H 0.4363 0.3377 0.7050 0.035 Uiso 1 1 calc R . . C8 C 0.41251(4) 0.39226(11) 0.62666(6) 0.0234(3) Uani 1 1 d . . . H8 H 0.4220 0.4590 0.6344 0.028 Uiso 1 1 calc R . . C9 C 0.39054(4) 0.36719(10) 0.57310(6) 0.0200(3) Uani 1 1 d . . . H9 H 0.3849 0.4174 0.5448 0.024 Uiso 1 1 calc R . . C10 C 0.30643(4) 0.16856(12) 0.23735(6) 0.0268(3) Uani 1 1 d . . . H10A H 0.2826 0.2043 0.2212 0.040 Uiso 1 1 calc R . . H10B H 0.3021 0.1096 0.2582 0.040 Uiso 1 1 calc R . . H10C H 0.3165 0.1464 0.2075 0.040 Uiso 1 1 calc R . . C11 C 0.33390(4) 0.23752(10) 0.27564(6) 0.0195(3) Uani 1 1 d . . . C12 C 0.37850(4) 0.34125(10) 0.30787(5) 0.0163(2) Uani 1 1 d . . . C13 C 0.41169(4) 0.40230(10) 0.30825(6) 0.0173(3) Uani 1 1 d . . . C14 C 0.42473(4) 0.39521(11) 0.26141(6) 0.0222(3) Uani 1 1 d . . . H14 H 0.4130 0.3494 0.2323 0.027 Uiso 1 1 calc R . . C15 C 0.45445(4) 0.45444(12) 0.25733(6) 0.0255(3) Uani 1 1 d . . . H15 H 0.4632 0.4484 0.2257 0.031 Uiso 1 1 calc R . . C16 C 0.47156(4) 0.52265(12) 0.29924(6) 0.0248(3) Uani 1 1 d . . . H16 H 0.4914 0.5646 0.2958 0.030 Uiso 1 1 calc R . . C17 C 0.45940(4) 0.52899(11) 0.34616(6) 0.0221(3) Uani 1 1 d . . . H17 H 0.4712 0.5749 0.3752 0.027 Uiso 1 1 calc R . . C18 C 0.42997(4) 0.46808(11) 0.35076(6) 0.0195(3) Uani 1 1 d . . . H18 H 0.4223 0.4715 0.3835 0.023 Uiso 1 1 calc R . . C19 C 0.21436(5) 0.23678(14) 0.32773(12) 0.0608(7) Uani 1 1 d . . . H19A H 0.1897 0.2496 0.3331 0.091 Uiso 1 1 calc R . . H19B H 0.2259 0.1775 0.3495 0.091 Uiso 1 1 calc R . . H19C H 0.2111 0.2244 0.2882 0.091 Uiso 1 1 calc R . . C20 C 0.23921(4) 0.32659(12) 0.34666(8) 0.0315(4) Uani 1 1 d . . . C21 C 0.25925(4) 0.47283(10) 0.37307(6) 0.0178(3) Uani 1 1 d . . . C22 C 0.25800(4) 0.57931(10) 0.38945(5) 0.0165(2) Uani 1 1 d . . . C23 C 0.23070(4) 0.60807(11) 0.41472(6) 0.0225(3) Uani 1 1 d . . . H23 H 0.2128 0.5602 0.4192 0.027 Uiso 1 1 calc R . . C24 C 0.22985(4) 0.70607(12) 0.43310(6) 0.0261(3) Uani 1 1 d . . . H24 H 0.2115 0.7251 0.4505 0.031 Uiso 1 1 calc R . . C25 C 0.25550(4) 0.77672(11) 0.42642(6) 0.0262(3) Uani 1 1 d . . . H25 H 0.2552 0.8434 0.4402 0.031 Uiso 1 1 calc R . . C26 C 0.28158(4) 0.74990(11) 0.39948(6) 0.0240(3) Uani 1 1 d . . . H26 H 0.2986 0.7989 0.3936 0.029 Uiso 1 1 calc R . . C27 C 0.28284(4) 0.65151(10) 0.38112(6) 0.0194(3) Uani 1 1 d . . . H27 H 0.3008 0.6334 0.3627 0.023 Uiso 1 1 calc R . . C28 C 0.41299(5) 0.79450(12) 0.39863(7) 0.0301(3) Uani 1 1 d . . . H28A H 0.4170 0.8339 0.3679 0.045 Uiso 1 1 calc R . . H28B H 0.4374 0.7725 0.4235 0.045 Uiso 1 1 calc R . . H28C H 0.4001 0.8364 0.4194 0.045 Uiso 1 1 calc R . . C29 C 0.38939(4) 0.70415(10) 0.37580(6) 0.0191(3) Uani 1 1 d . . . C30 C 0.35634(4) 0.59527(10) 0.32110(5) 0.0155(2) Uani 1 1 d . . . C31 C 0.33645(4) 0.54729(10) 0.26763(5) 0.0152(2) Uani 1 1 d . . . C32 C 0.30288(4) 0.49388(10) 0.25852(6) 0.0186(3) Uani 1 1 d . . . H32 H 0.2916 0.4875 0.2876 0.022 Uiso 1 1 calc R . . C33 C 0.28579(4) 0.44981(11) 0.20679(6) 0.0213(3) Uani 1 1 d . . . H33 H 0.2629 0.4132 0.2007 0.026 Uiso 1 1 calc R . . C34 C 0.30207(4) 0.45924(11) 0.16414(6) 0.0217(3) Uani 1 1 d . . . H34 H 0.2907 0.4281 0.1291 0.026 Uiso 1 1 calc R . . C35 C 0.33504(4) 0.51422(11) 0.17268(6) 0.0206(3) Uani 1 1 d . . . H35 H 0.3460 0.5215 0.1432 0.025 Uiso 1 1 calc R . . C36 C 0.35211(4) 0.55851(10) 0.22373(6) 0.0183(3) Uani 1 1 d . . . H36 H 0.3745 0.5967 0.2291 0.022 Uiso 1 1 calc R . . C37 C 0.28864(4) 0.42340(10) 0.50641(6) 0.0204(3) Uani 1 1 d . . . H37A H 0.2887 0.3749 0.4770 0.031 Uiso 1 1 calc R . . H37B H 0.2633 0.4516 0.4993 0.031 Uiso 1 1 calc R . . H37C H 0.2961 0.3891 0.5426 0.031 Uiso 1 1 calc R . . C38 C 0.31587(4) 0.50675(10) 0.50682(5) 0.0162(2) Uani 1 1 d . . . C39 C 0.34741(4) 0.64068(10) 0.53188(5) 0.0160(2) Uani 1 1 d . . . C40 C 0.36224(4) 0.73448(10) 0.56173(6) 0.0176(3) Uani 1 1 d . . . C41 C 0.36783(4) 0.73841(11) 0.61910(6) 0.0208(3) Uani 1 1 d . . . H41 H 0.3629 0.6805 0.6381 0.025 Uiso 1 1 calc R . . C42 C 0.38062(4) 0.82657(11) 0.64851(6) 0.0255(3) Uani 1 1 d . . . H42 H 0.3848 0.8288 0.6876 0.031 Uiso 1 1 calc R . . C43 C 0.38736(5) 0.91158(11) 0.62051(7) 0.0294(3) Uani 1 1 d . . . H43 H 0.3963 0.9718 0.6407 0.035 Uiso 1 1 calc R . . C44 C 0.38112(5) 0.90914(11) 0.56339(7) 0.0290(3) Uani 1 1 d . . . H44 H 0.3855 0.9678 0.5445 0.035 Uiso 1 1 calc R . . C45 C 0.36851(4) 0.82081(10) 0.53378(6) 0.0220(3) Uani 1 1 d . . . H45 H 0.3642 0.8191 0.4946 0.026 Uiso 1 1 calc R . . C46 C 0.47519(4) 0.61007(12) 0.55290(7) 0.0304(3) Uani 1 1 d . . . H46A H 0.4999 0.5890 0.5772 0.046 Uiso 1 1 calc R . . H46B H 0.4605 0.6399 0.5755 0.046 Uiso 1 1 calc R . . H46C H 0.4786 0.6602 0.5261 0.046 Uiso 1 1 calc R . . C47 C 0.45475(4) 0.52045(11) 0.52227(6) 0.0212(3) Uani 1 1 d . . . C48 C 0.43913(4) 0.37299(10) 0.49166(6) 0.0193(3) Uani 1 1 d . . . C49 C 0.44203(4) 0.26225(11) 0.48773(6) 0.0217(3) Uani 1 1 d . . . C50 C 0.42369(4) 0.20758(12) 0.44038(7) 0.0287(3) Uani 1 1 d . . . H50 H 0.4087 0.2417 0.4081 0.034 Uiso 1 1 calc R . . C51 C 0.42716(5) 0.10288(12) 0.43983(8) 0.0357(4) Uani 1 1 d . . . H51 H 0.4144 0.0660 0.4073 0.043 Uiso 1 1 calc R . . C52 C 0.44898(6) 0.05241(13) 0.48616(8) 0.0419(4) Uani 1 1 d . . . H52 H 0.4514 -0.0189 0.4855 0.050 Uiso 1 1 calc R . . C53 C 0.46731(6) 0.10648(14) 0.53378(8) 0.0443(5) Uani 1 1 d . . . H53 H 0.4822 0.0720 0.5660 0.053 Uiso 1 1 calc R . . C54 C 0.46397(5) 0.21079(12) 0.53458(7) 0.0339(4) Uani 1 1 d . . . H54 H 0.4767 0.2474 0.5673 0.041 Uiso 1 1 calc R . . C55 C 0.35204(6) 0.09830(14) 0.75378(8) 0.0401(4) Uani 1 1 d . . . H55A H 0.3623 0.1675 0.7548 0.048 Uiso 1 1 calc R . . H55B H 0.3369 0.0837 0.7149 0.048 Uiso 1 1 calc R . . Cl1 Cl 0.32262(2) 0.09284(5) 0.79723(3) 0.0854(3) Uani 1 1 d . . . Cl2 Cl 0.389754(18) 0.01157(4) 0.77419(2) 0.05774(15) Uani 1 1 d . . . N1 N 0.34523(3) 0.28343(8) 0.45560(5) 0.0171(2) Uani 1 1 d . . . N2 N 0.32534(3) 0.21218(8) 0.41781(5) 0.0182(2) Uani 1 1 d . . . N3 N 0.34222(4) 0.13684(9) 0.49944(5) 0.0284(3) Uani 1 1 d . . . N4 N 0.35984(3) 0.33970(8) 0.34624(5) 0.0152(2) Uani 1 1 d . . . N5 N 0.33134(3) 0.27053(8) 0.32499(5) 0.0165(2) Uani 1 1 d . . . N6 N 0.36312(3) 0.27921(9) 0.26402(5) 0.0200(2) Uani 1 1 d . . . N7 N 0.29036(3) 0.41965(8) 0.37542(4) 0.0148(2) Uani 1 1 d . . . N8 N 0.27676(3) 0.32528(8) 0.35735(5) 0.0184(2) Uani 1 1 d . . . N9 N 0.22715(4) 0.41765(10) 0.35569(7) 0.0312(3) Uani 1 1 d . . . N10 N 0.35969(3) 0.55908(8) 0.37208(4) 0.0139(2) Uani 1 1 d . . . N11 N 0.38093(3) 0.63136(8) 0.40726(4) 0.0152(2) Uani 1 1 d . . . N12 N 0.37445(3) 0.68474(9) 0.32192(5) 0.0191(2) Uani 1 1 d . . . N13 N 0.33882(3) 0.51037(8) 0.47519(4) 0.0147(2) Uani 1 1 d . . . N14 N 0.35922(3) 0.59769(8) 0.49143(4) 0.0145(2) Uani 1 1 d . . . N15 N 0.32022(3) 0.58542(8) 0.54237(5) 0.0182(2) Uani 1 1 d . . . N16 N 0.40953(3) 0.43019(8) 0.46502(5) 0.0159(2) Uani 1 1 d . . . N17 N 0.42009(3) 0.52623(8) 0.48559(5) 0.0158(2) Uani 1 1 d . . . N18 N 0.46757(3) 0.42632(9) 0.52712(5) 0.0243(3) Uani 1 1 d . . . Ni1 Ni 0.351130(4) 0.423336(12) 0.414443(7) 0.01305(5) 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 B1 0.0203(7) 0.0124(6) 0.0175(7) -0.0014(5) 0.0041(6) -0.0010(5) B2 0.0177(6) 0.0130(6) 0.0134(7) -0.0009(5) 0.0030(5) 0.0001(5) C1 0.0728(13) 0.0174(8) 0.0298(9) -0.0002(7) 0.0025(9) -0.0147(8) C2 0.0390(8) 0.0148(7) 0.0223(7) 0.0012(5) 0.0058(6) -0.0033(6) C3 0.0278(7) 0.0158(6) 0.0165(7) 0.0006(5) 0.0033(6) 0.0012(5) C4 0.0287(7) 0.0199(7) 0.0147(6) 0.0017(5) 0.0039(6) 0.0021(5) C5 0.0559(11) 0.0202(7) 0.0211(8) 0.0041(6) 0.0032(7) 0.0001(7) C6 0.0606(12) 0.0289(9) 0.0180(8) 0.0057(6) 0.0024(8) 0.0035(8) C7 0.0385(9) 0.0303(8) 0.0148(7) -0.0004(6) 0.0008(6) 0.0052(7) C8 0.0264(7) 0.0239(7) 0.0177(7) -0.0020(6) 0.0035(6) 0.0017(6) C9 0.0236(7) 0.0193(7) 0.0159(6) 0.0018(5) 0.0039(5) 0.0037(5) C10 0.0335(8) 0.0244(7) 0.0199(7) -0.0090(6) 0.0043(6) -0.0054(6) C11 0.0242(7) 0.0161(6) 0.0159(6) -0.0029(5) 0.0024(5) 0.0019(5) C12 0.0187(6) 0.0153(6) 0.0141(6) -0.0007(5) 0.0034(5) 0.0046(5) C13 0.0160(6) 0.0187(6) 0.0168(6) 0.0011(5) 0.0040(5) 0.0044(5) C14 0.0216(6) 0.0271(7) 0.0174(7) -0.0022(5) 0.0053(5) 0.0030(5) C15 0.0241(7) 0.0345(8) 0.0201(7) 0.0012(6) 0.0098(6) 0.0017(6) C16 0.0191(6) 0.0294(8) 0.0263(8) 0.0026(6) 0.0072(6) 0.0008(6) C17 0.0183(6) 0.0261(7) 0.0204(7) -0.0028(6) 0.0036(5) 0.0009(5) C18 0.0163(6) 0.0244(7) 0.0178(7) -0.0003(5) 0.0050(5) 0.0031(5) C19 0.0235(8) 0.0279(9) 0.126(2) -0.0230(12) 0.0148(11) -0.0090(7) C20 0.0189(7) 0.0204(7) 0.0522(11) -0.0059(7) 0.0062(7) -0.0031(6) C21 0.0175(6) 0.0182(6) 0.0174(6) 0.0006(5) 0.0048(5) 0.0002(5) C22 0.0159(6) 0.0176(6) 0.0141(6) -0.0005(5) 0.0014(5) 0.0030(5) C23 0.0198(6) 0.0264(7) 0.0216(7) 0.0012(6) 0.0067(6) 0.0033(5) C24 0.0249(7) 0.0313(8) 0.0219(7) -0.0020(6) 0.0066(6) 0.0112(6) C25 0.0308(8) 0.0202(7) 0.0225(7) -0.0028(6) 0.0001(6) 0.0094(6) C26 0.0248(7) 0.0163(6) 0.0282(8) 0.0009(6) 0.0037(6) 0.0012(5) C27 0.0185(6) 0.0181(6) 0.0207(7) -0.0006(5) 0.0048(5) 0.0030(5) C28 0.0431(9) 0.0222(7) 0.0227(8) 0.0000(6) 0.0062(7) -0.0134(7) C29 0.0230(6) 0.0170(6) 0.0165(6) 0.0013(5) 0.0051(5) -0.0021(5) C30 0.0160(6) 0.0161(6) 0.0147(6) -0.0007(5) 0.0049(5) 0.0020(4) C31 0.0181(6) 0.0146(6) 0.0117(6) 0.0011(5) 0.0025(5) 0.0041(5) C32 0.0225(6) 0.0189(6) 0.0142(6) 0.0014(5) 0.0050(5) 0.0007(5) C33 0.0212(6) 0.0210(7) 0.0195(7) 0.0002(5) 0.0029(5) -0.0020(5) C34 0.0267(7) 0.0224(7) 0.0133(6) -0.0017(5) 0.0021(5) 0.0032(6) C35 0.0243(7) 0.0235(7) 0.0145(6) 0.0012(5) 0.0066(5) 0.0050(5) C36 0.0194(6) 0.0191(6) 0.0163(6) 0.0030(5) 0.0054(5) 0.0039(5) C37 0.0233(7) 0.0204(7) 0.0187(7) 0.0003(5) 0.0083(6) -0.0027(5) C38 0.0189(6) 0.0167(6) 0.0125(6) 0.0010(5) 0.0038(5) 0.0019(5) C39 0.0200(6) 0.0151(6) 0.0123(6) 0.0008(5) 0.0039(5) 0.0038(5) C40 0.0205(6) 0.0155(6) 0.0164(6) -0.0012(5) 0.0048(5) 0.0031(5) C41 0.0280(7) 0.0179(6) 0.0163(6) -0.0009(5) 0.0062(6) -0.0009(5) C42 0.0379(8) 0.0220(7) 0.0158(7) -0.0038(5) 0.0069(6) -0.0023(6) C43 0.0479(10) 0.0165(7) 0.0228(8) -0.0042(6) 0.0090(7) -0.0031(6) C44 0.0472(9) 0.0143(7) 0.0258(8) 0.0012(6) 0.0114(7) 0.0000(6) C45 0.0332(7) 0.0166(6) 0.0162(6) 0.0011(5) 0.0074(6) 0.0043(5) C46 0.0211(7) 0.0248(8) 0.0353(9) -0.0078(7) -0.0069(6) 0.0002(6) C47 0.0185(6) 0.0202(7) 0.0214(7) -0.0023(5) 0.0007(5) 0.0011(5) C48 0.0190(6) 0.0191(7) 0.0178(6) 0.0003(5) 0.0026(5) 0.0038(5) C49 0.0199(6) 0.0184(7) 0.0251(7) -0.0004(5) 0.0040(6) 0.0052(5) C50 0.0304(8) 0.0229(7) 0.0270(8) -0.0023(6) -0.0003(6) 0.0086(6) C51 0.0414(9) 0.0220(8) 0.0362(9) -0.0077(7) 0.0002(8) 0.0073(7) C52 0.0478(10) 0.0198(8) 0.0502(12) -0.0011(8) 0.0028(9) 0.0107(7) C53 0.0535(11) 0.0259(9) 0.0400(11) 0.0042(8) -0.0064(9) 0.0132(8) C54 0.0383(9) 0.0237(8) 0.0300(9) 0.0006(7) -0.0044(7) 0.0073(7) C55 0.0519(11) 0.0358(10) 0.0386(10) -0.0099(8) 0.0225(9) -0.0116(8) Cl1 0.1271(6) 0.0659(4) 0.1002(5) -0.0409(4) 0.0905(5) -0.0536(4) Cl2 0.0795(4) 0.0392(3) 0.0417(3) -0.0079(2) -0.0014(3) 0.0021(3) N1 0.0215(5) 0.0141(5) 0.0141(5) -0.0018(4) 0.0031(4) -0.0003(4) N2 0.0241(6) 0.0128(5) 0.0164(5) -0.0015(4) 0.0042(5) -0.0015(4) N3 0.0451(8) 0.0161(6) 0.0204(6) 0.0020(5) 0.0044(6) -0.0049(5) N4 0.0163(5) 0.0128(5) 0.0151(5) -0.0015(4) 0.0025(4) 0.0000(4) N5 0.0197(5) 0.0132(5) 0.0151(5) -0.0019(4) 0.0029(4) -0.0007(4) N6 0.0235(6) 0.0195(6) 0.0162(6) -0.0037(4) 0.0046(5) 0.0021(4) N7 0.0180(5) 0.0121(5) 0.0139(5) -0.0012(4) 0.0043(4) -0.0014(4) N8 0.0190(5) 0.0139(5) 0.0207(6) -0.0016(4) 0.0037(5) -0.0026(4) N9 0.0180(6) 0.0214(6) 0.0519(9) -0.0075(6) 0.0070(6) -0.0028(5) N10 0.0149(5) 0.0141(5) 0.0123(5) -0.0019(4) 0.0032(4) 0.0007(4) N11 0.0187(5) 0.0127(5) 0.0139(5) -0.0021(4) 0.0042(4) -0.0015(4) N12 0.0248(6) 0.0162(5) 0.0161(6) 0.0011(4) 0.0054(5) -0.0021(4) N13 0.0173(5) 0.0122(5) 0.0136(5) -0.0006(4) 0.0033(4) -0.0006(4) N14 0.0180(5) 0.0115(5) 0.0126(5) -0.0010(4) 0.0026(4) 0.0001(4) N15 0.0226(5) 0.0178(5) 0.0146(5) -0.0008(4) 0.0062(5) 0.0012(4) N16 0.0181(5) 0.0137(5) 0.0152(5) -0.0017(4) 0.0036(4) 0.0012(4) N17 0.0171(5) 0.0135(5) 0.0157(5) -0.0018(4) 0.0031(4) 0.0009(4) N18 0.0198(6) 0.0216(6) 0.0264(7) -0.0036(5) -0.0007(5) 0.0035(5) Ni1 0.01529(8) 0.01162(8) 0.01161(8) -0.00095(6) 0.00306(6) 0.00049(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 N5 1.5324(18) . ? B1 N8 1.5384(18) . ? B1 N2 1.5412(19) . ? B1 H1 1.0000 . ? B2 N11 1.5321(18) . ? B2 N17 1.5396(18) . ? B2 N14 1.5451(17) . ? B2 H2 1.0000 . ? C1 C2 1.491(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N3 1.3223(19) . ? C2 N2 1.3425(18) . ? C3 N1 1.3433(17) . ? C3 N3 1.3593(18) . ? C3 C4 1.479(2) . ? C4 C9 1.391(2) . ? C4 C5 1.404(2) . ? C5 C6 1.385(2) . ? C5 H5 0.9500 . ? C6 C7 1.392(2) . ? C6 H6 0.9500 . ? C7 C8 1.382(2) . ? C7 H7 0.9500 . ? C8 C9 1.391(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.489(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N6 1.3273(18) . ? C11 N5 1.3460(17) . ? C12 N4 1.3472(16) . ? C12 N6 1.3569(17) . ? C12 C13 1.4731(18) . ? C13 C18 1.3890(19) . ? C13 C14 1.4049(18) . ? C14 C15 1.384(2) . ? C14 H14 0.9500 . ? C15 C16 1.389(2) . ? C15 H15 0.9500 . ? C16 C17 1.387(2) . ? C16 H16 0.9500 . ? C17 C18 1.3921(19) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.494(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 N9 1.330(2) . ? C20 N8 1.3411(18) . ? C21 N7 1.3410(16) . ? C21 N9 1.3559(18) . ? C21 C22 1.4734(18) . ? C22 C27 1.3887(19) . ? C22 C23 1.4022(18) . ? C23 C24 1.381(2) . ? C23 H23 0.9500 . ? C24 C25 1.382(2) . ? C24 H24 0.9500 . ? C25 C26 1.386(2) . ? C25 H25 0.9500 . ? C26 C27 1.3877(19) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 C29 1.493(2) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 N12 1.3268(18) . ? C29 N11 1.3429(17) . ? C30 N10 1.3392(16) . ? C30 N12 1.3601(17) . ? C30 C31 1.4712(18) . ? C31 C32 1.3928(18) . ? C31 C36 1.4019(17) . ? C32 C33 1.3939(19) . ? C32 H32 0.9500 . ? C33 C34 1.3862(19) . ? C33 H33 0.9500 . ? C34 C35 1.387(2) . ? C34 H34 0.9500 . ? C35 C36 1.3815(19) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 C38 1.4958(18) . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 N13 1.3308(16) . ? C38 N15 1.3507(17) . ? C39 N15 1.3369(17) . ? C39 N14 1.3490(16) . ? C39 C40 1.4706(18) . ? C40 C41 1.3961(18) . ? C40 C45 1.3977(19) . ? C41 C42 1.3877(19) . ? C41 H41 0.9500 . ? C42 C43 1.390(2) . ? C42 H42 0.9500 . ? C43 C44 1.386(2) . ? C43 H43 0.9500 . ? C44 C45 1.391(2) . ? C44 H44 0.9500 . ? C45 H45 0.9500 . ? C46 C47 1.493(2) . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 N18 1.3270(18) . ? C47 N17 1.3446(18) . ? C48 N16 1.3391(17) . ? C48 N18 1.3597(18) . ? C48 C49 1.4759(19) . ? C49 C50 1.386(2) . ? C49 C54 1.394(2) . ? C50 C51 1.393(2) . ? C50 H50 0.9500 . ? C51 C52 1.377(3) . ? C51 H51 0.9500 . ? C52 C53 1.387(3) . ? C52 H52 0.9500 . ? C53 C54 1.388(2) . ? C53 H53 0.9500 . ? C54 H54 0.9500 . ? C55 Cl1 1.7642(18) . ? C55 Cl2 1.766(2) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? N1 N2 1.3856(15) . ? N1 Ni1 2.1652(11) . ? N4 N5 1.3817(15) . ? N4 Ni1 2.1463(11) . ? N7 N8 1.3735(15) . ? N7 Ni1 2.1789(11) . ? N10 N11 1.3802(15) . ? N10 Ni1 2.1612(11) . ? N13 N14 1.3763(14) . ? N13 Ni1 2.0715(10) . ? N16 N17 1.3847(15) . ? N16 Ni1 2.1661(11) . ? 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 N5 B1 N8 109.63(11) . . ? N5 B1 N2 110.91(11) . . ? N8 B1 N2 107.61(11) . . ? N5 B1 H1 109.6 . . ? N8 B1 H1 109.6 . . ? N2 B1 H1 109.6 . . ? N11 B2 N17 108.62(10) . . ? N11 B2 N14 110.04(11) . . ? N17 B2 N14 108.18(10) . . ? N11 B2 H2 110.0 . . ? N17 B2 H2 110.0 . . ? N14 B2 H2 110.0 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N3 C2 N2 111.18(13) . . ? N3 C2 C1 123.59(14) . . ? N2 C2 C1 125.23(14) . . ? N1 C3 N3 112.85(12) . . ? N1 C3 C4 129.28(12) . . ? N3 C3 C4 117.88(12) . . ? C9 C4 C5 118.09(13) . . ? C9 C4 C3 125.26(13) . . ? C5 C4 C3 116.66(13) . . ? C6 C5 C4 120.77(15) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 120.48(15) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 119.09(14) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C7 C8 C9 120.61(14) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C4 120.89(13) . . ? C8 C9 H9 119.6 . . ? C4 C9 H9 119.6 . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C11 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N6 C11 N5 110.88(12) . . ? N6 C11 C10 124.16(12) . . ? N5 C11 C10 124.86(13) . . ? N4 C12 N6 112.99(11) . . ? N4 C12 C13 127.90(12) . . ? N6 C12 C13 119.09(11) . . ? C18 C13 C14 118.36(12) . . ? C18 C13 C12 124.43(12) . . ? C14 C13 C12 117.18(12) . . ? C15 C14 C13 120.55(14) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 120.44(13) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 119.54(13) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 120.02(14) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C13 C18 C17 121.03(12) . . ? C13 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N9 C20 N8 111.23(13) . . ? N9 C20 C19 124.61(14) . . ? N8 C20 C19 124.16(14) . . ? N7 C21 N9 113.35(12) . . ? N7 C21 C22 126.10(12) . . ? N9 C21 C22 120.49(12) . . ? C27 C22 C23 119.10(12) . . ? C27 C22 C21 122.58(12) . . ? C23 C22 C21 118.32(12) . . ? C24 C23 C22 119.94(13) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 120.64(13) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C24 C25 C26 119.73(14) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C25 C26 C27 120.11(14) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C26 C27 C22 120.39(12) . . ? C26 C27 H27 119.8 . . ? C22 C27 H27 119.8 . . ? C29 C28 H28A 109.5 . . ? C29 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C29 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N12 C29 N11 111.24(12) . . ? N12 C29 C28 124.49(12) . . ? N11 C29 C28 124.27(12) . . ? N10 C30 N12 113.17(11) . . ? N10 C30 C31 126.72(12) . . ? N12 C30 C31 120.10(11) . . ? C32 C31 C36 119.17(12) . . ? C32 C31 C30 123.41(11) . . ? C36 C31 C30 117.41(12) . . ? C31 C32 C33 120.14(12) . . ? C31 C32 H32 119.9 . . ? C33 C32 H32 119.9 . . ? C34 C33 C32 120.13(13) . . ? C34 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? C33 C34 C35 119.88(13) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C36 C35 C34 120.41(12) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C35 C36 C31 120.23(13) . . ? C35 C36 H36 119.9 . . ? C31 C36 H36 119.9 . . ? C38 C37 H37A 109.5 . . ? C38 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C38 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? N13 C38 N15 113.37(11) . . ? N13 C38 C37 125.21(12) . . ? N15 C38 C37 121.37(11) . . ? N15 C39 N14 110.74(11) . . ? N15 C39 C40 123.50(11) . . ? N14 C39 C40 125.75(12) . . ? C41 C40 C45 119.59(13) . . ? C41 C40 C39 118.44(12) . . ? C45 C40 C39 121.84(12) . . ? C42 C41 C40 120.24(13) . . ? C42 C41 H41 119.9 . . ? C40 C41 H41 119.9 . . ? C41 C42 C43 119.76(13) . . ? C41 C42 H42 120.1 . . ? C43 C42 H42 120.1 . . ? C44 C43 C42 120.46(14) . . ? C44 C43 H43 119.8 . . ? C42 C43 H43 119.8 . . ? C43 C44 C45 120.00(14) . . ? C43 C44 H44 120.0 . . ? C45 C44 H44 120.0 . . ? C44 C45 C40 119.93(13) . . ? C44 C45 H45 120.0 . . ? C40 C45 H45 120.0 . . ? C47 C46 H46A 109.5 . . ? C47 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C47 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? N18 C47 N17 111.16(12) . . ? N18 C47 C46 125.85(13) . . ? N17 C47 C46 122.99(12) . . ? N16 C48 N18 113.35(12) . . ? N16 C48 C49 126.44(12) . . ? N18 C48 C49 120.12(12) . . ? C50 C49 C54 118.95(14) . . ? C50 C49 C48 123.33(13) . . ? C54 C49 C48 117.71(13) . . ? C49 C50 C51 120.34(15) . . ? C49 C50 H50 119.8 . . ? C51 C50 H50 119.8 . . ? C52 C51 C50 120.49(16) . . ? C52 C51 H51 119.8 . . ? C50 C51 H51 119.8 . . ? C51 C52 C53 119.55(16) . . ? C51 C52 H52 120.2 . . ? C53 C52 H52 120.2 . . ? C52 C53 C54 120.22(17) . . ? C52 C53 H53 119.9 . . ? C54 C53 H53 119.9 . . ? C53 C54 C49 120.44(16) . . ? C53 C54 H54 119.8 . . ? C49 C54 H54 119.8 . . ? Cl1 C55 Cl2 112.29(11) . . ? Cl1 C55 H55A 109.1 . . ? Cl2 C55 H55A 109.1 . . ? Cl1 C55 H55B 109.1 . . ? Cl2 C55 H55B 109.1 . . ? H55A C55 H55B 107.9 . . ? C3 N1 N2 103.58(10) . . ? C3 N1 Ni1 144.93(9) . . ? N2 N1 Ni1 111.37(8) . . ? C2 N2 N1 108.08(11) . . ? C2 N2 B1 128.46(12) . . ? N1 N2 B1 122.83(10) . . ? C2 N3 C3 104.31(12) . . ? C12 N4 N5 103.48(10) . . ? C12 N4 Ni1 142.94(9) . . ? N5 N4 Ni1 111.69(7) . . ? C11 N5 N4 108.32(11) . . ? C11 N5 B1 129.16(11) . . ? N4 N5 B1 122.46(10) . . ? C11 N6 C12 104.29(11) . . ? C21 N7 N8 103.63(10) . . ? C21 N7 Ni1 140.66(9) . . ? N8 N7 Ni1 113.53(8) . . ? C20 N8 N7 108.23(11) . . ? C20 N8 B1 131.03(12) . . ? N7 N8 B1 120.52(10) . . ? C20 N9 C21 103.54(12) . . ? C30 N10 N11 103.71(10) . . ? C30 N10 Ni1 141.67(9) . . ? N11 N10 Ni1 113.65(8) . . ? C29 N11 N10 108.07(10) . . ? C29 N11 B2 129.87(11) . . ? N10 N11 B2 121.88(10) . . ? C29 N12 C30 103.79(11) . . ? C38 N13 N14 104.37(10) . . ? C38 N13 Ni1 138.07(9) . . ? N14 N13 Ni1 117.54(8) . . ? C39 N14 N13 107.65(10) . . ? C39 N14 B2 132.12(11) . . ? N13 N14 B2 119.13(10) . . ? C39 N15 C38 103.86(11) . . ? C48 N16 N17 103.52(10) . . ? C48 N16 Ni1 143.13(9) . . ? N17 N16 Ni1 112.35(8) . . ? C47 N17 N16 108.10(11) . . ? C47 N17 B2 128.58(11) . . ? N16 N17 B2 123.13(10) . . ? C47 N18 C48 103.88(12) . . ? N13 Ni1 N4 174.95(4) . . ? N13 Ni1 N10 89.92(4) . . ? N4 Ni1 N10 87.44(4) . . ? N13 Ni1 N1 92.69(4) . . ? N4 Ni1 N1 90.10(4) . . ? N10 Ni1 N1 176.71(4) . . ? N13 Ni1 N16 87.01(4) . . ? N4 Ni1 N16 97.26(4) . . ? N10 Ni1 N16 89.14(4) . . ? N1 Ni1 N16 89.00(4) . . ? N13 Ni1 N7 85.19(4) . . ? N4 Ni1 N7 90.73(4) . . ? N10 Ni1 N7 94.73(4) . . ? N1 Ni1 N7 87.49(4) . . ? N16 Ni1 N7 171.28(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 C3 C4 C9 2.7(2) . . . . ? N3 C3 C4 C9 -177.52(14) . . . . ? N1 C3 C4 C5 -176.66(15) . . . . ? N3 C3 C4 C5 3.1(2) . . . . ? C9 C4 C5 C6 -2.2(2) . . . . ? C3 C4 C5 C6 177.23(16) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C8 2.2(3) . . . . ? C6 C7 C8 C9 -1.7(2) . . . . ? C7 C8 C9 C4 -0.8(2) . . . . ? C5 C4 C9 C8 2.7(2) . . . . ? C3 C4 C9 C8 -176.65(14) . . . . ? N4 C12 C13 C18 1.8(2) . . . . ? N6 C12 C13 C18 -179.73(13) . . . . ? N4 C12 C13 C14 -176.08(13) . . . . ? N6 C12 C13 C14 2.35(18) . . . . ? C18 C13 C14 C15 -1.6(2) . . . . ? C12 C13 C14 C15 176.40(13) . . . . ? C13 C14 C15 C16 -0.7(2) . . . . ? C14 C15 C16 C17 1.9(2) . . . . ? C15 C16 C17 C18 -0.7(2) . . . . ? C14 C13 C18 C17 2.9(2) . . . . ? C12 C13 C18 C17 -175.02(13) . . . . ? C16 C17 C18 C13 -1.7(2) . . . . ? N7 C21 C22 C27 35.6(2) . . . . ? N9 C21 C22 C27 -147.28(14) . . . . ? N7 C21 C22 C23 -144.04(14) . . . . ? N9 C21 C22 C23 33.1(2) . . . . ? C27 C22 C23 C24 -2.8(2) . . . . ? C21 C22 C23 C24 176.83(13) . . . . ? C22 C23 C24 C25 0.6(2) . . . . ? C23 C24 C25 C26 2.0(2) . . . . ? C24 C25 C26 C27 -2.4(2) . . . . ? C25 C26 C27 C22 0.1(2) . . . . ? C23 C22 C27 C26 2.4(2) . . . . ? C21 C22 C27 C26 -177.17(13) . . . . ? N10 C30 C31 C32 37.4(2) . . . . ? N12 C30 C31 C32 -144.00(13) . . . . ? N10 C30 C31 C36 -143.93(13) . . . . ? N12 C30 C31 C36 34.64(17) . . . . ? C36 C31 C32 C33 1.86(19) . . . . ? C30 C31 C32 C33 -179.53(12) . . . . ? C31 C32 C33 C34 -0.2(2) . . . . ? C32 C33 C34 C35 -1.2(2) . . . . ? C33 C34 C35 C36 0.9(2) . . . . ? C34 C35 C36 C31 0.7(2) . . . . ? C32 C31 C36 C35 -2.11(19) . . . . ? C30 C31 C36 C35 179.19(12) . . . . ? N15 C39 C40 C41 40.35(19) . . . . ? N14 C39 C40 C41 -138.66(14) . . . . ? N15 C39 C40 C45 -135.54(14) . . . . ? N14 C39 C40 C45 45.5(2) . . . . ? C45 C40 C41 C42 -1.9(2) . . . . ? C39 C40 C41 C42 -177.92(13) . . . . ? C40 C41 C42 C43 0.9(2) . . . . ? C41 C42 C43 C44 0.5(3) . . . . ? C42 C43 C44 C45 -0.9(3) . . . . ? C43 C44 C45 C40 -0.2(2) . . . . ? C41 C40 C45 C44 1.6(2) . . . . ? C39 C40 C45 C44 177.40(13) . . . . ? N16 C48 C49 C50 30.3(2) . . . . ? N18 C48 C49 C50 -153.23(15) . . . . ? N16 C48 C49 C54 -148.77(15) . . . . ? N18 C48 C49 C54 27.7(2) . . . . ? C54 C49 C50 C51 0.1(2) . . . . ? C48 C49 C50 C51 -178.92(15) . . . . ? C49 C50 C51 C52 -0.3(3) . . . . ? C50 C51 C52 C53 0.6(3) . . . . ? C51 C52 C53 C54 -0.6(3) . . . . ? C52 C53 C54 C49 0.4(3) . . . . ? C50 C49 C54 C53 -0.1(3) . . . . ? C48 C49 C54 C53 178.97(17) . . . . ? N3 C3 N1 N2 -0.26(15) . . . . ? C4 C3 N1 N2 179.53(14) . . . . ? N3 C3 N1 Ni1 -175.46(12) . . . . ? C4 C3 N1 Ni1 4.3(3) . . . . ? N3 C2 N2 N1 -0.44(17) . . . . ? C1 C2 N2 N1 179.60(16) . . . . ? N3 C2 N2 B1 -171.35(13) . . . . ? C1 C2 N2 B1 8.7(3) . . . . ? C3 N1 N2 C2 0.41(14) . . . . ? Ni1 N1 N2 C2 177.45(9) . . . . ? C3 N1 N2 B1 171.94(12) . . . . ? Ni1 N1 N2 B1 -11.02(14) . . . . ? N5 B1 N2 C2 -125.01(15) . . . . ? N8 B1 N2 C2 115.09(15) . . . . ? N5 B1 N2 N1 65.29(15) . . . . ? N8 B1 N2 N1 -54.62(15) . . . . ? N2 C2 N3 C3 0.27(18) . . . . ? C1 C2 N3 C3 -179.77(16) . . . . ? N1 C3 N3 C2 0.00(17) . . . . ? C4 C3 N3 C2 -179.81(13) . . . . ? N6 C12 N4 N5 1.07(14) . . . . ? C13 C12 N4 N5 179.58(12) . . . . ? N6 C12 N4 Ni1 -160.39(11) . . . . ? C13 C12 N4 Ni1 18.1(2) . . . . ? N6 C11 N5 N4 1.68(15) . . . . ? C10 C11 N5 N4 -174.79(13) . . . . ? N6 C11 N5 B1 -175.53(12) . . . . ? C10 C11 N5 B1 8.0(2) . . . . ? C12 N4 N5 C11 -1.61(13) . . . . ? Ni1 N4 N5 C11 166.49(8) . . . . ? C12 N4 N5 B1 175.82(11) . . . . ? Ni1 N4 N5 B1 -16.08(14) . . . . ? N8 B1 N5 C11 -111.55(15) . . . . ? N2 B1 N5 C11 129.76(14) . . . . ? N8 B1 N5 N4 71.60(15) . . . . ? N2 B1 N5 N4 -47.09(15) . . . . ? N5 C11 N6 C12 -0.97(15) . . . . ? C10 C11 N6 C12 175.53(13) . . . . ? N4 C12 N6 C11 -0.11(15) . . . . ? C13 C12 N6 C11 -178.76(12) . . . . ? N9 C21 N7 N8 1.10(15) . . . . ? C22 C21 N7 N8 178.43(12) . . . . ? N9 C21 N7 Ni1 -159.63(11) . . . . ? C22 C21 N7 Ni1 17.7(2) . . . . ? N9 C20 N8 N7 1.22(19) . . . . ? C19 C20 N8 N7 -178.08(19) . . . . ? N9 C20 N8 B1 175.74(14) . . . . ? C19 C20 N8 B1 -3.6(3) . . . . ? C21 N7 N8 C20 -1.36(15) . . . . ? Ni1 N7 N8 C20 165.45(11) . . . . ? C21 N7 N8 B1 -176.56(12) . . . . ? Ni1 N7 N8 B1 -9.75(14) . . . . ? N5 B1 N8 C20 133.15(16) . . . . ? N2 B1 N8 C20 -106.14(17) . . . . ? N5 B1 N8 N7 -52.89(16) . . . . ? N2 B1 N8 N7 67.82(14) . . . . ? N8 C20 N9 C21 -0.5(2) . . . . ? C19 C20 N9 C21 178.8(2) . . . . ? N7 C21 N9 C20 -0.39(18) . . . . ? C22 C21 N9 C20 -177.90(14) . . . . ? N12 C30 N10 N11 0.79(14) . . . . ? C31 C30 N10 N11 179.44(11) . . . . ? N12 C30 N10 Ni1 -166.22(10) . . . . ? C31 C30 N10 Ni1 12.4(2) . . . . ? N12 C29 N11 N10 0.97(15) . . . . ? C28 C29 N11 N10 -178.30(13) . . . . ? N12 C29 N11 B2 176.08(12) . . . . ? C28 C29 N11 B2 -3.2(2) . . . . ? C30 N10 N11 C29 -1.03(13) . . . . ? Ni1 N10 N11 C29 170.21(8) . . . . ? C30 N10 N11 B2 -176.61(11) . . . . ? Ni1 N10 N11 B2 -5.37(13) . . . . ? N17 B2 N11 C29 -111.08(15) . . . . ? N14 B2 N11 C29 130.67(13) . . . . ? N17 B2 N11 N10 63.45(14) . . . . ? N14 B2 N11 N10 -54.80(15) . . . . ? N11 C29 N12 C30 -0.46(15) . . . . ? C28 C29 N12 C30 178.80(14) . . . . ? N10 C30 N12 C29 -0.23(15) . . . . ? C31 C30 N12 C29 -178.99(11) . . . . ? N15 C38 N13 N14 -0.25(14) . . . . ? C37 C38 N13 N14 -177.73(12) . . . . ? N15 C38 N13 Ni1 178.08(9) . . . . ? C37 C38 N13 Ni1 0.6(2) . . . . ? N15 C39 N14 N13 -0.26(14) . . . . ? C40 C39 N14 N13 178.85(12) . . . . ? N15 C39 N14 B2 -167.76(12) . . . . ? C40 C39 N14 B2 11.3(2) . . . . ? C38 N13 N14 C39 0.30(13) . . . . ? Ni1 N13 N14 C39 -178.44(8) . . . . ? C38 N13 N14 B2 169.71(11) . . . . ? Ni1 N13 N14 B2 -9.03(14) . . . . ? N11 B2 N14 C39 -129.02(14) . . . . ? N17 B2 N14 C39 112.46(14) . . . . ? N11 B2 N14 N13 64.63(14) . . . . ? N17 B2 N14 N13 -53.89(14) . . . . ? N14 C39 N15 C38 0.11(14) . . . . ? C40 C39 N15 C38 -179.03(12) . . . . ? N13 C38 N15 C39 0.09(15) . . . . ? C37 C38 N15 C39 177.69(12) . . . . ? N18 C48 N16 N17 -0.46(15) . . . . ? C49 C48 N16 N17 176.23(13) . . . . ? N18 C48 N16 Ni1 -167.00(11) . . . . ? C49 C48 N16 Ni1 9.7(2) . . . . ? N18 C47 N17 N16 -0.14(16) . . . . ? C46 C47 N17 N16 -179.94(13) . . . . ? N18 C47 N17 B2 174.86(12) . . . . ? C46 C47 N17 B2 -4.9(2) . . . . ? C48 N16 N17 C47 0.35(14) . . . . ? Ni1 N16 N17 C47 171.67(9) . . . . ? C48 N16 N17 B2 -174.98(11) . . . . ? Ni1 N16 N17 B2 -3.66(14) . . . . ? N11 B2 N17 C47 127.98(14) . . . . ? N14 B2 N17 C47 -112.60(14) . . . . ? N11 B2 N17 N16 -57.70(15) . . . . ? N14 B2 N17 N16 61.72(15) . . . . ? N17 C47 N18 C48 -0.14(16) . . . . ? C46 C47 N18 C48 179.65(14) . . . . ? N16 C48 N18 C47 0.39(16) . . . . ? C49 C48 N18 C47 -176.54(13) . . . . ? C38 N13 Ni1 N10 144.10(13) . . . . ? N14 N13 Ni1 N10 -37.74(9) . . . . ? C38 N13 Ni1 N1 -37.91(14) . . . . ? N14 N13 Ni1 N1 140.26(9) . . . . ? C38 N13 Ni1 N16 -126.76(14) . . . . ? N14 N13 Ni1 N16 51.40(9) . . . . ? C38 N13 Ni1 N7 49.34(13) . . . . ? N14 N13 Ni1 N7 -132.49(9) . . . . ? C12 N4 Ni1 N10 31.40(15) . . . . ? N5 N4 Ni1 N10 -129.17(8) . . . . ? C12 N4 Ni1 N1 -146.40(15) . . . . ? N5 N4 Ni1 N1 53.03(8) . . . . ? C12 N4 Ni1 N16 -57.40(15) . . . . ? N5 N4 Ni1 N16 142.03(8) . . . . ? C12 N4 Ni1 N7 126.11(15) . . . . ? N5 N4 Ni1 N7 -34.46(8) . . . . ? C30 N10 Ni1 N13 -148.78(14) . . . . ? N11 N10 Ni1 N13 45.01(8) . . . . ? C30 N10 Ni1 N4 26.90(14) . . . . ? N11 N10 Ni1 N4 -139.30(8) . . . . ? C30 N10 Ni1 N16 124.21(14) . . . . ? N11 N10 Ni1 N16 -41.99(8) . . . . ? C30 N10 Ni1 N7 -63.61(14) . . . . ? N11 N10 Ni1 N7 130.18(8) . . . . ? C3 N1 Ni1 N13 -48.29(16) . . . . ? N2 N1 Ni1 N13 136.72(8) . . . . ? C3 N1 Ni1 N4 135.92(16) . . . . ? N2 N1 Ni1 N4 -39.07(8) . . . . ? C3 N1 Ni1 N16 38.66(16) . . . . ? N2 N1 Ni1 N16 -136.33(8) . . . . ? C3 N1 Ni1 N7 -133.36(16) . . . . ? N2 N1 Ni1 N7 51.65(8) . . . . ? C48 N16 Ni1 N13 121.99(15) . . . . ? N17 N16 Ni1 N13 -43.84(8) . . . . ? C48 N16 Ni1 N4 -60.73(15) . . . . ? N17 N16 Ni1 N4 133.43(8) . . . . ? C48 N16 Ni1 N10 -148.04(15) . . . . ? N17 N16 Ni1 N10 46.12(8) . . . . ? C48 N16 Ni1 N1 29.24(15) . . . . ? N17 N16 Ni1 N1 -136.59(8) . . . . ? C21 N7 Ni1 N13 24.80(14) . . . . ? N8 N7 Ni1 N13 -134.72(9) . . . . ? C21 N7 Ni1 N4 -152.21(14) . . . . ? N8 N7 Ni1 N4 48.26(8) . . . . ? C21 N7 Ni1 N10 -64.72(14) . . . . ? N8 N7 Ni1 N10 135.76(8) . . . . ? C21 N7 Ni1 N1 117.72(14) . . . . ? N8 N7 Ni1 N1 -41.81(8) . . . . ? _diffrn_measured_fraction_theta_max 0.867 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.540 _refine_diff_density_min -0.583 _refine_diff_density_rms 0.063 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.046 0.250 375 73 ' ' 2 0.500 -0.046 0.750 375 73 ' ' 3 0.287 0.202 0.547 14 1 ' ' 4 0.713 0.202 0.953 14 1 ' ' 5 0.000 0.454 0.750 375 73 ' ' 6 0.000 0.546 0.250 375 73 ' ' 7 0.213 0.298 0.453 14 1 ' ' 8 0.787 0.298 0.047 15 1 ' ' 9 0.213 0.702 0.953 14 1 ' ' 10 0.787 0.702 0.547 14 1 ' ' 11 0.287 0.798 0.047 15 1 ' ' 12 0.713 0.798 0.453 14 1 ' ' _platon_squeeze_details ; ; data_08mz481_0m _database_code_depnum_ccdc_archive 'CCDC 850802' #TrackingRef '- combined cifs - new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H27 B Cl N9 Ni O' _chemical_formula_weight 598.55 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' Ni Ni 0.3393 1.1124 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 12.1457(10) _cell_length_b 16.6085(13) _cell_length_c 13.3465(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.630(2) _cell_angle_gamma 90.00 _cell_volume 2692.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3130 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 29.47 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.860 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.827 _exptl_absorpt_correction_T_max 0.934 _exptl_absorpt_process_details 'Apex2 v2008.2-4 (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 17561 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 28.28 _reflns_number_total 6615 _reflns_number_gt 4812 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2008.2-4 (Bruker, 2008)' _computing_cell_refinement 'Apex2 v2008.2-4 ' _computing_data_reduction 'Apex2 v2008.2-4 ' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0639P)^2^+1.7657P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6615 _refine_ls_number_parameters 370 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0811 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1258 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.4785(3) 0.3629(2) 0.7319(3) 0.0219(7) Uani 1 1 d . . . H1 H 0.4133 0.3265 0.7244 0.026 Uiso 1 1 calc R . . C1 C 0.5194(3) 0.17866(19) 0.6815(3) 0.0292(7) Uani 1 1 d . . . H1A H 0.5515 0.1273 0.6606 0.044 Uiso 1 1 calc R . . H1B H 0.4567 0.1919 0.6376 0.044 Uiso 1 1 calc R . . H1C H 0.4943 0.1743 0.7508 0.044 Uiso 1 1 calc R . . C2 C 0.6039(3) 0.24327(18) 0.6746(2) 0.0226(6) Uani 1 1 d . . . C3 C 0.7484(2) 0.31029(18) 0.6470(2) 0.0211(6) Uani 1 1 d . . . C4 C 0.8546(2) 0.32978(18) 0.5999(2) 0.0233(6) Uani 1 1 d . . . C5 C 0.9490(3) 0.2860(2) 0.6211(3) 0.0318(8) Uani 1 1 d . . . H5 H 0.9500 0.2478 0.6742 0.038 Uiso 1 1 calc R . . C6 C 1.0429(3) 0.2986(2) 0.5635(3) 0.0395(9) Uani 1 1 d . . . H6 H 1.1080 0.2685 0.5770 0.047 Uiso 1 1 calc R . . C7 C 1.0414(3) 0.3547(2) 0.4868(3) 0.0401(9) Uani 1 1 d . . . H7 H 1.1050 0.3620 0.4471 0.048 Uiso 1 1 calc R . . C8 C 0.9485(3) 0.4000(2) 0.4675(3) 0.0340(8) Uani 1 1 d . . . H8 H 0.9487 0.4394 0.4159 0.041 Uiso 1 1 calc R . . C9 C 0.8554(3) 0.3876(2) 0.5237(3) 0.0284(7) Uani 1 1 d . . . H9 H 0.7912 0.4187 0.5105 0.034 Uiso 1 1 calc R . . C10 C 0.3292(3) 0.3270(2) 0.9195(3) 0.0264(7) Uani 1 1 d . . . H10A H 0.3395 0.2706 0.9001 0.040 Uiso 1 1 calc R . . H10B H 0.2818 0.3539 0.8699 0.040 Uiso 1 1 calc R . . H10C H 0.2947 0.3294 0.9854 0.040 Uiso 1 1 calc R . . C11 C 0.4383(2) 0.36826(17) 0.9240(2) 0.0215(6) Uani 1 1 d . . . C12 C 0.5884(2) 0.42229(17) 0.9728(2) 0.0198(6) Uani 1 1 d . . . C13 C 0.6779(3) 0.44593(18) 1.0416(2) 0.0225(6) Uani 1 1 d . . . C14 C 0.6712(3) 0.4241(2) 1.1421(2) 0.0292(7) Uani 1 1 d . . . H14 H 0.6072 0.3977 1.1657 0.035 Uiso 1 1 calc R . . C15 C 0.7578(3) 0.4407(2) 1.2079(3) 0.0348(8) Uani 1 1 d . . . H15 H 0.7531 0.4246 1.2761 0.042 Uiso 1 1 calc R . . C16 C 0.8507(3) 0.4804(2) 1.1749(3) 0.0340(8) Uani 1 1 d . . . H16 H 0.9089 0.4930 1.2205 0.041 Uiso 1 1 calc R . . C17 C 0.8582(3) 0.5016(2) 1.0761(3) 0.0290(7) Uani 1 1 d . . . H17 H 0.9222 0.5286 1.0533 0.035 Uiso 1 1 calc R . . C18 C 0.7738(3) 0.48422(19) 1.0084(3) 0.0265(7) Uani 1 1 d . . . H18 H 0.7809 0.4983 0.9398 0.032 Uiso 1 1 calc R . . C19 C 0.2762(3) 0.4155(2) 0.5938(3) 0.0348(8) Uani 1 1 d . . . H19A H 0.2315 0.4131 0.6544 0.052 Uiso 1 1 calc R . . H19B H 0.2976 0.3608 0.5742 0.052 Uiso 1 1 calc R . . H19C H 0.2333 0.4403 0.5394 0.052 Uiso 1 1 calc R . . C20 C 0.3770(3) 0.46435(19) 0.6141(2) 0.0257(7) Uani 1 1 d . . . C21 C 0.4896(3) 0.56116(19) 0.6230(2) 0.0235(6) Uani 1 1 d . . . C22 C 0.5339(3) 0.6430(2) 0.6117(2) 0.0289(7) Uani 1 1 d . . . C23 C 0.4582(3) 0.7039(2) 0.5879(3) 0.0401(9) Uani 1 1 d . . . H23 H 0.3831 0.6907 0.5758 0.048 Uiso 1 1 calc R . . C24 C 0.4920(4) 0.7825(2) 0.5818(3) 0.0497(11) Uani 1 1 d . . . H24 H 0.4400 0.8239 0.5678 0.060 Uiso 1 1 calc R . . C25 C 0.6029(4) 0.8017(2) 0.5962(3) 0.0506(11) Uani 1 1 d . . . H25 H 0.6257 0.8563 0.5921 0.061 Uiso 1 1 calc R . . C26 C 0.6796(3) 0.7430(2) 0.6162(3) 0.0366(8) Uani 1 1 d . . . H26 H 0.7552 0.7565 0.6241 0.044 Uiso 1 1 calc R . . C27 C 0.6447(3) 0.6622(2) 0.6249(2) 0.0301(7) Uani 1 1 d . . . H27 H 0.6967 0.6210 0.6397 0.036 Uiso 1 1 calc R . . Cl1 Cl 0.85377(7) 0.50531(6) 0.73296(8) 0.0411(2) Uani 1 1 d . . . N1 N 0.5837(2) 0.32037(14) 0.69701(19) 0.0203(5) Uani 1 1 d . . . N2 N 0.67809(19) 0.36410(15) 0.68135(19) 0.0206(5) Uani 1 1 d . . . N3 N 0.7067(2) 0.23385(15) 0.6443(2) 0.0232(6) Uani 1 1 d . . . N4 N 0.49673(19) 0.38597(14) 0.84273(19) 0.0200(5) Uani 1 1 d . . . N5 N 0.5936(2) 0.42188(14) 0.87303(19) 0.0207(5) Uani 1 1 d . . . N6 N 0.4920(2) 0.39080(15) 1.00674(19) 0.0219(5) Uani 1 1 d . . . N7 N 0.4620(2) 0.43977(15) 0.67046(19) 0.0222(5) Uani 1 1 d . . . N8 N 0.5364(2) 0.50237(15) 0.67742(19) 0.0214(5) Uani 1 1 d . . . N9 N 0.3923(2) 0.53960(17) 0.5822(2) 0.0276(6) Uani 1 1 d . . . Ni1 Ni 0.67609(3) 0.47785(2) 0.75618(3) 0.01927(12) Uani 1 1 d . . . O1 O 0.65570(18) 0.58654(13) 0.83300(17) 0.0239(5) Uani 1 1 d D . . H1D H 0.704(2) 0.6227(18) 0.844(3) 0.036 Uiso 1 1 d D . . H1E H 0.606(2) 0.594(2) 0.878(2) 0.036 Uiso 1 1 d 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 0.0204(16) 0.0170(17) 0.0286(19) -0.0024(14) 0.0070(14) 0.0000(12) C1 0.0286(16) 0.0148(16) 0.044(2) -0.0028(14) 0.0099(14) -0.0050(12) C2 0.0246(15) 0.0185(15) 0.0250(17) 0.0019(12) 0.0045(12) 0.0003(11) C3 0.0233(15) 0.0178(15) 0.0223(16) -0.0005(12) 0.0038(12) 0.0013(11) C4 0.0225(15) 0.0182(15) 0.0294(17) -0.0070(12) 0.0085(12) -0.0029(11) C5 0.0270(17) 0.0227(17) 0.046(2) -0.0016(15) 0.0063(15) -0.0024(13) C6 0.0229(17) 0.030(2) 0.066(3) -0.0094(18) 0.0068(17) -0.0011(14) C7 0.0299(18) 0.044(2) 0.047(2) -0.0075(18) 0.0130(16) -0.0134(16) C8 0.0383(19) 0.0296(19) 0.0343(19) -0.0034(15) 0.0093(16) -0.0073(15) C9 0.0282(16) 0.0232(17) 0.0339(18) -0.0052(14) 0.0069(14) -0.0017(13) C10 0.0260(16) 0.0224(17) 0.0310(18) 0.0009(13) 0.0110(13) -0.0025(12) C11 0.0242(15) 0.0130(14) 0.0273(17) -0.0006(12) 0.0093(12) 0.0025(11) C12 0.0228(14) 0.0126(14) 0.0240(16) 0.0016(11) 0.0080(12) 0.0024(11) C13 0.0283(16) 0.0120(14) 0.0271(17) -0.0021(12) 0.0040(13) 0.0054(11) C14 0.0291(17) 0.0293(19) 0.0294(18) -0.0017(14) 0.0067(14) 0.0046(13) C15 0.039(2) 0.040(2) 0.0251(18) -0.0045(15) 0.0009(14) 0.0098(16) C16 0.0298(17) 0.034(2) 0.038(2) -0.0119(16) -0.0035(15) 0.0066(14) C17 0.0278(16) 0.0196(16) 0.040(2) -0.0062(14) 0.0021(14) 0.0020(12) C18 0.0287(16) 0.0187(16) 0.0321(18) -0.0027(13) 0.0039(13) 0.0022(12) C19 0.0299(17) 0.030(2) 0.045(2) -0.0053(16) -0.0044(15) -0.0024(14) C20 0.0262(15) 0.0239(17) 0.0269(17) -0.0050(13) 0.0019(13) 0.0003(12) C21 0.0273(16) 0.0187(16) 0.0247(16) 0.0021(12) 0.0068(12) 0.0019(12) C22 0.0374(18) 0.0197(17) 0.0296(18) 0.0049(13) 0.0041(14) 0.0009(13) C23 0.042(2) 0.029(2) 0.050(2) 0.0113(17) -0.0027(17) 0.0014(16) C24 0.056(3) 0.022(2) 0.071(3) 0.0121(19) -0.007(2) 0.0027(18) C25 0.071(3) 0.025(2) 0.056(3) 0.0138(18) 0.002(2) -0.0127(19) C26 0.046(2) 0.030(2) 0.033(2) 0.0031(15) 0.0027(16) -0.0072(16) C27 0.0349(18) 0.0278(19) 0.0276(18) 0.0033(14) 0.0065(14) -0.0042(14) Cl1 0.0266(4) 0.0360(5) 0.0610(6) -0.0200(4) 0.0138(4) -0.0093(3) N1 0.0232(12) 0.0129(12) 0.0250(14) -0.0013(10) 0.0062(10) -0.0018(9) N2 0.0191(12) 0.0150(13) 0.0278(14) -0.0017(10) 0.0070(10) -0.0017(9) N3 0.0266(13) 0.0144(13) 0.0286(15) -0.0001(10) 0.0068(11) -0.0014(10) N4 0.0190(12) 0.0135(12) 0.0275(14) -0.0006(10) 0.0066(10) -0.0013(9) N5 0.0214(12) 0.0142(12) 0.0267(14) -0.0003(10) 0.0058(10) -0.0018(9) N6 0.0241(13) 0.0156(13) 0.0261(14) -0.0008(10) 0.0076(11) 0.0003(10) N7 0.0226(13) 0.0175(13) 0.0265(14) -0.0023(10) 0.0053(10) -0.0007(10) N8 0.0233(13) 0.0166(13) 0.0245(14) -0.0009(10) 0.0071(10) -0.0032(10) N9 0.0293(14) 0.0244(15) 0.0292(15) -0.0005(11) 0.0014(11) 0.0037(11) Ni1 0.01991(19) 0.0136(2) 0.0245(2) -0.00060(15) 0.00724(14) -0.00128(14) O1 0.0263(11) 0.0160(11) 0.0297(12) -0.0040(9) 0.0129(9) -0.0033(8) _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 N7 1.530(4) . ? B1 N1 1.537(4) . ? B1 N4 1.542(4) . ? B1 H1 1.0000 . ? C1 C2 1.489(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N3 1.326(4) . ? C2 N1 1.338(4) . ? C3 N2 1.321(4) . ? C3 N3 1.367(4) . ? C3 C4 1.477(4) . ? C4 C5 1.385(4) . ? C4 C9 1.399(5) . ? C5 C6 1.398(5) . ? C5 H5 0.9500 . ? C6 C7 1.384(6) . ? C6 H6 0.9500 . ? C7 C8 1.378(5) . ? C7 H7 0.9500 . ? C8 C9 1.379(5) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.493(4) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N6 1.330(4) . ? C11 N4 1.335(4) . ? C12 N5 1.334(4) . ? C12 N6 1.364(4) . ? C12 C13 1.468(4) . ? C13 C14 1.393(5) . ? C13 C18 1.403(4) . ? C14 C15 1.391(5) . ? C14 H14 0.9500 . ? C15 C16 1.384(5) . ? C15 H15 0.9500 . ? C16 C17 1.369(5) . ? C16 H16 0.9500 . ? C17 C18 1.389(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.491(4) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 N9 1.334(4) . ? C20 N7 1.335(4) . ? C21 N8 1.340(4) . ? C21 N9 1.344(4) . ? C21 C22 1.470(5) . ? C22 C27 1.392(5) . ? C22 C23 1.402(5) . ? C23 C24 1.371(5) . ? C23 H23 0.9500 . ? C24 C25 1.395(6) . ? C24 H24 0.9500 . ? C25 C26 1.373(6) . ? C25 H25 0.9500 . ? C26 C27 1.413(5) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? Cl1 Ni1 2.2307(9) . ? N1 N2 1.375(3) . ? N2 Ni1 2.137(2) . ? N4 N5 1.376(3) . ? N5 Ni1 2.082(2) . ? N7 N8 1.379(3) . ? N8 Ni1 2.028(3) . ? Ni1 O1 2.092(2) . ? O1 H1D 0.853(18) . ? O1 H1E 0.857(18) . ? 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 N7 B1 N1 108.9(3) . . ? N7 B1 N4 108.8(2) . . ? N1 B1 N4 107.1(2) . . ? N7 B1 H1 110.6 . . ? N1 B1 H1 110.6 . . ? N4 B1 H1 110.6 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N3 C2 N1 110.9(3) . . ? N3 C2 C1 125.9(3) . . ? N1 C2 C1 123.2(3) . . ? N2 C3 N3 113.4(3) . . ? N2 C3 C4 124.8(3) . . ? N3 C3 C4 121.1(3) . . ? C5 C4 C9 119.8(3) . . ? C5 C4 C3 121.5(3) . . ? C9 C4 C3 118.2(3) . . ? C4 C5 C6 119.2(3) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C7 C6 C5 120.2(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C6 120.7(3) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 119.4(3) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C8 C9 C4 120.7(3) . . ? C8 C9 H9 119.7 . . ? C4 C9 H9 119.7 . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C11 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N6 C11 N4 110.6(3) . . ? N6 C11 C10 126.2(3) . . ? N4 C11 C10 123.2(3) . . ? N5 C12 N6 112.3(3) . . ? N5 C12 C13 125.6(3) . . ? N6 C12 C13 121.8(3) . . ? C14 C13 C18 118.7(3) . . ? C14 C13 C12 118.8(3) . . ? C18 C13 C12 122.4(3) . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 120.5(3) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 119.5(3) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 121.2(3) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C17 C18 C13 119.9(3) . . ? C17 C18 H18 120.1 . . ? C13 C18 H18 120.1 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N9 C20 N7 110.9(3) . . ? N9 C20 C19 124.7(3) . . ? N7 C20 C19 124.3(3) . . ? N8 C21 N9 113.0(3) . . ? N8 C21 C22 125.2(3) . . ? N9 C21 C22 121.8(3) . . ? C27 C22 C23 119.6(3) . . ? C27 C22 C21 123.6(3) . . ? C23 C22 C21 116.8(3) . . ? C24 C23 C22 120.3(4) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 119.9(4) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C26 C25 C24 121.1(4) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C25 C26 C27 119.1(4) . . ? C25 C26 H26 120.4 . . ? C27 C26 H26 120.4 . . ? C22 C27 C26 119.9(3) . . ? C22 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C2 N1 N2 108.4(2) . . ? C2 N1 B1 131.5(3) . . ? N2 N1 B1 120.1(2) . . ? C3 N2 N1 103.8(2) . . ? C3 N2 Ni1 140.4(2) . . ? N1 N2 Ni1 112.46(17) . . ? C2 N3 C3 103.4(2) . . ? C11 N4 N5 108.5(2) . . ? C11 N4 B1 130.7(3) . . ? N5 N4 B1 120.2(2) . . ? C12 N5 N4 104.2(2) . . ? C12 N5 Ni1 140.7(2) . . ? N4 N5 Ni1 112.97(18) . . ? C11 N6 C12 104.3(3) . . ? C20 N7 N8 108.0(3) . . ? C20 N7 B1 130.8(3) . . ? N8 N7 B1 120.8(3) . . ? C21 N8 N7 103.9(3) . . ? C21 N8 Ni1 140.8(2) . . ? N7 N8 Ni1 115.27(19) . . ? C20 N9 C21 104.2(3) . . ? N8 Ni1 N5 94.09(10) . . ? N8 Ni1 O1 88.73(10) . . ? N5 Ni1 O1 87.57(9) . . ? N8 Ni1 N2 87.08(10) . . ? N5 Ni1 N2 87.90(10) . . ? O1 Ni1 N2 173.60(9) . . ? N8 Ni1 Cl1 133.82(8) . . ? N5 Ni1 Cl1 132.02(8) . . ? O1 Ni1 Cl1 90.67(7) . . ? N2 Ni1 Cl1 95.73(7) . . ? Ni1 O1 H1D 127(3) . . ? Ni1 O1 H1E 123(3) . . ? H1D O1 H1E 106(3) . . ? 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 C3 C4 C5 138.3(3) . . . . ? N3 C3 C4 C5 -52.2(4) . . . . ? N2 C3 C4 C9 -49.3(4) . . . . ? N3 C3 C4 C9 120.2(3) . . . . ? C9 C4 C5 C6 -2.1(5) . . . . ? C3 C4 C5 C6 170.2(3) . . . . ? C4 C5 C6 C7 0.5(5) . . . . ? C5 C6 C7 C8 1.4(6) . . . . ? C6 C7 C8 C9 -1.7(6) . . . . ? C7 C8 C9 C4 0.1(5) . . . . ? C5 C4 C9 C8 1.8(5) . . . . ? C3 C4 C9 C8 -170.8(3) . . . . ? N5 C12 C13 C14 -163.6(3) . . . . ? N6 C12 C13 C14 10.3(4) . . . . ? N5 C12 C13 C18 11.3(5) . . . . ? N6 C12 C13 C18 -174.8(3) . . . . ? C18 C13 C14 C15 0.5(5) . . . . ? C12 C13 C14 C15 175.7(3) . . . . ? C13 C14 C15 C16 1.2(5) . . . . ? C14 C15 C16 C17 -1.7(5) . . . . ? C15 C16 C17 C18 0.4(5) . . . . ? C16 C17 C18 C13 1.4(5) . . . . ? C14 C13 C18 C17 -1.8(5) . . . . ? C12 C13 C18 C17 -176.7(3) . . . . ? N8 C21 C22 C27 23.8(5) . . . . ? N9 C21 C22 C27 -160.0(3) . . . . ? N8 C21 C22 C23 -155.3(3) . . . . ? N9 C21 C22 C23 21.0(5) . . . . ? C27 C22 C23 C24 -2.8(6) . . . . ? C21 C22 C23 C24 176.2(4) . . . . ? C22 C23 C24 C25 2.1(7) . . . . ? C23 C24 C25 C26 0.2(7) . . . . ? C24 C25 C26 C27 -1.7(6) . . . . ? C23 C22 C27 C26 1.3(5) . . . . ? C21 C22 C27 C26 -177.7(3) . . . . ? C25 C26 C27 C22 0.9(5) . . . . ? N3 C2 N1 N2 -0.4(4) . . . . ? C1 C2 N1 N2 -179.1(3) . . . . ? N3 C2 N1 B1 177.9(3) . . . . ? C1 C2 N1 B1 -0.8(5) . . . . ? N7 B1 N1 C2 -133.4(3) . . . . ? N4 B1 N1 C2 109.0(4) . . . . ? N7 B1 N1 N2 44.8(4) . . . . ? N4 B1 N1 N2 -72.8(3) . . . . ? N3 C3 N2 N1 -3.0(3) . . . . ? C4 C3 N2 N1 167.1(3) . . . . ? N3 C3 N2 Ni1 153.1(2) . . . . ? C4 C3 N2 Ni1 -36.8(5) . . . . ? C2 N1 N2 C3 2.0(3) . . . . ? B1 N1 N2 C3 -176.5(3) . . . . ? C2 N1 N2 Ni1 -161.7(2) . . . . ? B1 N1 N2 Ni1 19.7(3) . . . . ? N1 C2 N3 C3 -1.3(3) . . . . ? C1 C2 N3 C3 177.3(3) . . . . ? N2 C3 N3 C2 2.8(4) . . . . ? C4 C3 N3 C2 -167.7(3) . . . . ? N6 C11 N4 N5 0.0(3) . . . . ? C10 C11 N4 N5 -178.6(3) . . . . ? N6 C11 N4 B1 171.1(3) . . . . ? C10 C11 N4 B1 -7.6(5) . . . . ? N7 B1 N4 C11 118.4(3) . . . . ? N1 B1 N4 C11 -123.9(3) . . . . ? N7 B1 N4 N5 -71.4(3) . . . . ? N1 B1 N4 N5 46.2(3) . . . . ? N6 C12 N5 N4 -1.9(3) . . . . ? C13 C12 N5 N4 172.5(3) . . . . ? N6 C12 N5 Ni1 159.2(2) . . . . ? C13 C12 N5 Ni1 -26.4(5) . . . . ? C11 N4 N5 C12 1.1(3) . . . . ? B1 N4 N5 C12 -171.1(2) . . . . ? C11 N4 N5 Ni1 -166.03(18) . . . . ? B1 N4 N5 Ni1 21.8(3) . . . . ? N4 C11 N6 C12 -1.1(3) . . . . ? C10 C11 N6 C12 177.5(3) . . . . ? N5 C12 N6 C11 1.9(3) . . . . ? C13 C12 N6 C11 -172.7(3) . . . . ? N9 C20 N7 N8 0.9(3) . . . . ? C19 C20 N7 N8 -176.3(3) . . . . ? N9 C20 N7 B1 173.2(3) . . . . ? C19 C20 N7 B1 -4.0(5) . . . . ? N1 B1 N7 C20 123.8(3) . . . . ? N4 B1 N7 C20 -119.8(3) . . . . ? N1 B1 N7 N8 -64.8(3) . . . . ? N4 B1 N7 N8 51.6(3) . . . . ? N9 C21 N8 N7 -0.4(3) . . . . ? C22 C21 N8 N7 176.2(3) . . . . ? N9 C21 N8 Ni1 176.2(2) . . . . ? C22 C21 N8 Ni1 -7.2(5) . . . . ? C20 N7 N8 C21 -0.3(3) . . . . ? B1 N7 N8 C21 -173.5(3) . . . . ? C20 N7 N8 Ni1 -178.0(2) . . . . ? B1 N7 N8 Ni1 8.9(3) . . . . ? N7 C20 N9 C21 -1.1(3) . . . . ? C19 C20 N9 C21 176.1(3) . . . . ? N8 C21 N9 C20 0.9(4) . . . . ? C22 C21 N9 C20 -175.8(3) . . . . ? C21 N8 Ni1 N5 138.5(3) . . . . ? N7 N8 Ni1 N5 -45.1(2) . . . . ? C21 N8 Ni1 O1 51.0(3) . . . . ? N7 N8 Ni1 O1 -132.6(2) . . . . ? C21 N8 Ni1 N2 -133.8(3) . . . . ? N7 N8 Ni1 N2 42.6(2) . . . . ? C21 N8 Ni1 Cl1 -38.7(4) . . . . ? N7 N8 Ni1 Cl1 137.70(16) . . . . ? C12 N5 Ni1 N8 -130.8(3) . . . . ? N4 N5 Ni1 N8 29.24(19) . . . . ? C12 N5 Ni1 O1 -42.3(3) . . . . ? N4 N5 Ni1 O1 117.80(19) . . . . ? C12 N5 Ni1 N2 142.3(3) . . . . ? N4 N5 Ni1 N2 -57.68(19) . . . . ? C12 N5 Ni1 Cl1 46.4(4) . . . . ? N4 N5 Ni1 Cl1 -153.50(14) . . . . ? C3 N2 Ni1 N8 147.3(3) . . . . ? N1 N2 Ni1 N8 -57.9(2) . . . . ? C3 N2 Ni1 N5 -118.5(3) . . . . ? N1 N2 Ni1 N5 36.3(2) . . . . ? C3 N2 Ni1 Cl1 13.5(3) . . . . ? N1 N2 Ni1 Cl1 168.31(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1E N6 0.857(18) 1.980(19) 2.832(3) 173(4) 3_667 O1 H1D N3 0.853(18) 2.14(2) 2.976(3) 165(4) 2_656 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.167 _refine_diff_density_min -0.672 _refine_diff_density_rms 0.092 data_09mz175_0m _database_code_depnum_ccdc_archive 'CCDC 850803' #TrackingRef '- combined cifs - new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H50 B2 Cu N18' _chemical_formula_weight 1036.28 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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 24.899(3) _cell_length_b 13.9223(18) _cell_length_c 16.092(2) _cell_angle_alpha 90.00 _cell_angle_beta 120.3208(19) _cell_angle_gamma 90.00 _cell_volume 4815.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5227 _cell_measurement_theta_min 2.5675 _cell_measurement_theta_max 30.7405 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2156 _exptl_absorpt_coefficient_mu 0.515 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.676328 _exptl_absorpt_correction_T_max 0.862280 _exptl_absorpt_process_details 'TWINABS (Sheldrick, 2007)' _exptl_special_details ; The crystal under investigation was found to be non-merohedrally twinned. The orientation matrices for the two components were identified using the program Cell_Now, and the two components were integrated using Saint, resulting in a total of 16696 reflections. 15278 reflections (6880 unique ones) involved component 1 only (mean I/sigma = 6.1), 15227 reflections (7017 unique ones) involved component 2 only (mean I/sigma = 4.6), and 5996 reflections (4310 unique ones) involved both components (mean I/sigma = 11.4). The exact twin matrix identified by the integration program was found to be 0.46618 -1.57107 -0.03448, -0.48749 -0.47768 0.01134, -0.48896 0.52406 -0.98850. The data were corrected for absorption using twinabs, and the structure was solved using direct methods with only the non-overlapping reflections of component 1. The structure was refined using the hklf 5 routine with all reflections of component 1 (including the overlapping ones) below a d-spacing threshold of 0.75, resulting in a BASF value of 0.351(1). The Rint value given is for all reflections before the cutoff at d = 0.75 and is based on agreement between observed single and composite intensities and those calculated from refined unique intensities and twin fractions (TWINABS (Sheldrick, 2007)). ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 36501 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 28.28 _reflns_number_total 6518 _reflns_number_gt 5645 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2008.2-4 (Bruker, 2008)' _computing_cell_refinement 'Apex2 v2008.2-4' _computing_data_reduction 'Apex2 v2008.2-4' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0341P)^2^+7.2057P] 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 6518 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.92437(13) 0.24662(15) 0.02538(14) 0.0145(4) Uani 1 1 d . . . H1 H 0.9039 0.2452 -0.0464 0.017 Uiso 1 1 calc R . . C1 C 0.98843(11) 0.34581(16) -0.07939(15) 0.0213(4) Uani 1 1 d . . . H1A H 1.0091 0.3935 -0.0985 0.032 Uiso 1 1 calc R . . H1B H 0.9432 0.3522 -0.1205 0.032 Uiso 1 1 calc R . . H1C H 1.0012 0.2811 -0.0865 0.032 Uiso 1 1 calc R . . C2 C 1.00635(10) 0.36200(14) 0.02310(14) 0.0157(4) Uani 1 1 d . . . C3 C 1.05244(10) 0.40875(14) 0.16793(14) 0.0155(4) Uani 1 1 d . . . C4 C 1.09443(10) 0.47010(14) 0.25083(14) 0.0165(4) Uani 1 1 d . . . C5 C 1.14515(11) 0.51119(15) 0.25001(16) 0.0211(4) Uani 1 1 d . . . H5 H 1.1523 0.4973 0.1986 0.025 Uiso 1 1 calc R . . C6 C 1.18535(11) 0.57211(16) 0.32335(17) 0.0244(5) Uani 1 1 d . . . H6 H 1.2200 0.5994 0.3223 0.029 Uiso 1 1 calc R . . C7 C 1.17489(11) 0.59306(15) 0.39835(17) 0.0244(5) Uani 1 1 d . . . H7 H 1.2025 0.6343 0.4490 0.029 Uiso 1 1 calc R . . C8 C 1.12418(11) 0.55377(15) 0.39909(16) 0.0215(4) Uani 1 1 d . . . H8 H 1.1168 0.5688 0.4501 0.026 Uiso 1 1 calc R . . C9 C 1.08376(10) 0.49233(14) 0.32584(15) 0.0179(4) Uani 1 1 d . . . H9 H 1.0490 0.4656 0.3269 0.021 Uiso 1 1 calc R . . C10 C 0.88601(11) 0.04213(15) -0.07798(14) 0.0199(4) Uani 1 1 d . . . H10A H 0.8954 -0.0150 -0.1038 0.030 Uiso 1 1 calc R . . H10B H 0.8814 0.0978 -0.1184 0.030 Uiso 1 1 calc R . . H10C H 0.8472 0.0319 -0.0775 0.030 Uiso 1 1 calc R . . C11 C 0.93764(10) 0.05997(14) 0.02200(14) 0.0157(4) Uani 1 1 d . . . C12 C 1.01330(10) 0.04019(14) 0.16341(14) 0.0151(4) Uani 1 1 d . . . C13 C 1.06430(10) -0.01212(14) 0.24541(14) 0.0155(4) Uani 1 1 d . . . C14 C 1.06148(11) -0.11249(15) 0.24328(16) 0.0209(4) Uani 1 1 d . . . H14 H 1.0279 -0.1442 0.1903 0.025 Uiso 1 1 calc R . . C15 C 1.10720(11) -0.16560(15) 0.31759(17) 0.0244(5) Uani 1 1 d . . . H15 H 1.1046 -0.2337 0.3160 0.029 Uiso 1 1 calc R . . C16 C 1.15698(11) -0.12013(16) 0.39464(16) 0.0233(5) Uani 1 1 d . . . H16 H 1.1883 -0.1569 0.4459 0.028 Uiso 1 1 calc R . . C17 C 1.16087(11) -0.02035(16) 0.39656(16) 0.0203(4) Uani 1 1 d . . . H17 H 1.1951 0.0109 0.4490 0.024 Uiso 1 1 calc R . . C18 C 1.11500(10) 0.03335(15) 0.32246(14) 0.0176(4) Uani 1 1 d . . . H18 H 1.1180 0.1014 0.3239 0.021 Uiso 1 1 calc R . . C19 C 0.80304(11) 0.37837(16) -0.08953(15) 0.0226(5) Uani 1 1 d . . . H19A H 0.7583 0.3916 -0.1210 0.034 Uiso 1 1 calc R . . H19B H 0.8112 0.3352 -0.1301 0.034 Uiso 1 1 calc R . . H19C H 0.8257 0.4387 -0.0800 0.034 Uiso 1 1 calc R . . C20 C 0.82424(10) 0.33200(14) 0.00563(14) 0.0158(4) Uani 1 1 d . . . C21 C 0.83453(10) 0.29325(14) 0.13938(14) 0.0158(4) Uani 1 1 d . . . C22 C 0.82072(10) 0.28308(14) 0.21789(15) 0.0179(4) Uani 1 1 d . . . C23 C 0.76793(11) 0.32854(16) 0.20840(17) 0.0233(5) Uani 1 1 d . . . H23 H 0.7412 0.3632 0.1513 0.028 Uiso 1 1 calc R . . C24 C 0.75415(12) 0.32346(17) 0.28199(18) 0.0283(5) Uani 1 1 d . . . H24 H 0.7182 0.3546 0.2754 0.034 Uiso 1 1 calc R . . C25 C 0.79305(12) 0.27282(16) 0.36476(18) 0.0266(5) Uani 1 1 d . . . H25 H 0.7839 0.2698 0.4153 0.032 Uiso 1 1 calc R . . C26 C 0.84502(12) 0.22654(16) 0.37503(16) 0.0235(5) Uani 1 1 d . . . H26 H 0.8712 0.1914 0.4321 0.028 Uiso 1 1 calc R . . C27 C 0.85915(10) 0.23147(14) 0.30121(15) 0.0182(4) Uani 1 1 d . . . H27 H 0.8949 0.1996 0.3080 0.022 Uiso 1 1 calc R . . Cu1 Cu 1.0000 0.24228(2) 0.2500 0.01365(8) Uani 1 2 d S . . N1 N 1.01171(8) 0.34235(12) 0.16293(11) 0.0139(3) Uani 1 1 d . . . N2 N 0.98122(8) 0.31429(12) 0.06746(12) 0.0144(3) Uani 1 1 d . . . N3 N 1.05054(8) 0.42181(12) 0.08266(12) 0.0167(3) Uani 1 1 d . . . N4 N 0.99825(8) 0.13376(12) 0.15989(11) 0.0145(3) Uani 1 1 d . . . N5 N 0.94892(8) 0.14553(12) 0.06667(12) 0.0142(3) Uani 1 1 d . . . N6 N 0.97668(8) -0.00661(12) 0.07992(12) 0.0163(3) Uani 1 1 d . . . N7 N 0.88541(8) 0.25770(12) 0.14311(12) 0.0153(3) Uani 1 1 d . . . N8 N 0.87768(8) 0.28163(12) 0.05482(12) 0.0146(3) Uani 1 1 d . . . N9 N 0.79547(8) 0.34029(12) 0.05581(12) 0.0184(4) 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 B1 0.0165(10) 0.0138(10) 0.0115(8) 0.0007(8) 0.0059(9) -0.0004(9) C1 0.0254(11) 0.0217(10) 0.0185(10) 0.0015(8) 0.0123(9) -0.0017(9) C2 0.0185(10) 0.0133(8) 0.0163(9) 0.0037(7) 0.0094(8) 0.0030(8) C3 0.0144(9) 0.0140(8) 0.0171(10) 0.0022(7) 0.0073(8) 0.0039(8) C4 0.0169(10) 0.0118(8) 0.0159(9) 0.0022(7) 0.0045(8) 0.0002(8) C5 0.0207(11) 0.0198(10) 0.0212(10) 0.0030(8) 0.0095(9) 0.0003(9) C6 0.0177(10) 0.0201(10) 0.0308(12) 0.0015(9) 0.0088(10) -0.0054(9) C7 0.0202(11) 0.0164(9) 0.0247(11) -0.0026(8) 0.0025(9) -0.0007(9) C8 0.0223(11) 0.0163(9) 0.0201(10) -0.0008(8) 0.0065(9) 0.0027(9) C9 0.0163(10) 0.0145(9) 0.0199(10) 0.0019(8) 0.0070(8) 0.0020(8) C10 0.0215(11) 0.0190(9) 0.0167(10) -0.0034(8) 0.0078(9) -0.0009(9) C11 0.0175(10) 0.0163(9) 0.0170(10) -0.0024(8) 0.0115(8) -0.0033(8) C12 0.0167(10) 0.0150(9) 0.0171(10) -0.0012(7) 0.0111(8) -0.0011(8) C13 0.0181(10) 0.0168(9) 0.0152(9) 0.0030(7) 0.0111(8) 0.0030(8) C14 0.0229(11) 0.0181(9) 0.0227(11) -0.0012(8) 0.0122(9) -0.0005(9) C15 0.0261(12) 0.0151(9) 0.0336(13) 0.0052(9) 0.0162(10) 0.0044(9) C16 0.0205(11) 0.0250(11) 0.0241(11) 0.0097(9) 0.0110(9) 0.0085(9) C17 0.0174(10) 0.0250(10) 0.0206(10) 0.0028(9) 0.0113(9) 0.0024(9) C18 0.0216(10) 0.0165(9) 0.0186(10) -0.0004(8) 0.0129(9) -0.0002(8) C19 0.0226(11) 0.0209(10) 0.0181(10) 0.0019(8) 0.0057(9) 0.0030(9) C20 0.0132(9) 0.0142(9) 0.0165(9) -0.0012(7) 0.0050(8) -0.0021(8) C21 0.0164(10) 0.0127(8) 0.0183(10) -0.0024(7) 0.0089(8) -0.0019(8) C22 0.0198(10) 0.0148(9) 0.0222(10) -0.0033(8) 0.0129(9) -0.0036(8) C23 0.0225(11) 0.0223(10) 0.0303(12) 0.0018(9) 0.0171(10) 0.0032(9) C24 0.0288(12) 0.0273(11) 0.0374(14) -0.0019(10) 0.0230(11) 0.0019(10) C25 0.0356(13) 0.0241(11) 0.0309(12) -0.0042(9) 0.0248(11) -0.0045(11) C26 0.0289(12) 0.0199(10) 0.0240(11) -0.0003(9) 0.0152(10) -0.0040(10) C27 0.0187(10) 0.0173(9) 0.0206(10) -0.0028(8) 0.0113(9) -0.0034(9) Cu1 0.01688(17) 0.01182(16) 0.01276(15) 0.000 0.00786(15) 0.000 N1 0.0133(8) 0.0138(7) 0.0120(8) -0.0015(6) 0.0044(7) -0.0013(7) N2 0.0156(8) 0.0144(7) 0.0122(8) 0.0007(6) 0.0063(7) 0.0009(7) N3 0.0173(9) 0.0154(8) 0.0169(8) 0.0022(7) 0.0083(7) -0.0001(7) N4 0.0143(8) 0.0156(8) 0.0126(8) 0.0020(6) 0.0059(7) 0.0017(7) N5 0.0143(8) 0.0153(7) 0.0124(8) -0.0004(6) 0.0064(7) -0.0013(7) N6 0.0179(8) 0.0159(8) 0.0175(8) -0.0018(7) 0.0107(7) 0.0000(7) N7 0.0168(8) 0.0153(7) 0.0141(8) -0.0010(6) 0.0080(7) -0.0010(7) N8 0.0159(8) 0.0145(7) 0.0117(8) 0.0000(6) 0.0057(7) -0.0005(7) N9 0.0167(9) 0.0154(8) 0.0205(9) -0.0015(7) 0.0075(7) -0.0013(7) _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 N8 1.540(3) . ? B1 N2 1.543(3) . ? B1 N5 1.545(3) . ? B1 H1 1.0000 . ? C1 C2 1.492(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N3 1.326(3) . ? C2 N2 1.339(3) . ? C3 N1 1.344(3) . ? C3 N3 1.361(3) . ? C3 C4 1.481(3) . ? C4 C5 1.393(3) . ? C4 C9 1.395(3) . ? C5 C6 1.386(3) . ? C5 H5 0.9500 . ? C6 C7 1.388(3) . ? C6 H6 0.9500 . ? C7 C8 1.382(3) . ? C7 H7 0.9500 . ? C8 C9 1.391(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.488(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N6 1.326(3) . ? C11 N5 1.346(2) . ? C12 N4 1.349(3) . ? C12 N6 1.351(3) . ? C12 C13 1.481(3) . ? C13 C18 1.397(3) . ? C13 C14 1.399(3) . ? C14 C15 1.378(3) . ? C14 H14 0.9500 . ? C15 C16 1.387(3) . ? C15 H15 0.9500 . ? C16 C17 1.392(3) . ? C16 H16 0.9500 . ? C17 C18 1.382(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.491(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 N9 1.328(3) . ? C20 N8 1.351(3) . ? C21 N7 1.333(3) . ? C21 N9 1.365(3) . ? C21 C22 1.474(3) . ? C22 C27 1.391(3) . ? C22 C23 1.396(3) . ? C23 C24 1.391(3) . ? C23 H23 0.9500 . ? C24 C25 1.381(4) . ? C24 H24 0.9500 . ? C25 C26 1.379(3) . ? C25 H25 0.9500 . ? C26 C27 1.400(3) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? Cu1 N4 2.0792(17) 2_755 ? Cu1 N4 2.0793(17) . ? Cu1 N1 2.0980(16) . ? Cu1 N1 2.0980(16) 2_755 ? N1 N2 1.382(2) . ? N4 N5 1.388(2) . ? N7 N8 1.375(2) . ? 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 N8 B1 N2 109.85(15) . . ? N8 B1 N5 110.63(16) . . ? N2 B1 N5 106.94(18) . . ? N8 B1 H1 109.8 . . ? N2 B1 H1 109.8 . . ? N5 B1 H1 109.8 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N3 C2 N2 111.51(17) . . ? N3 C2 C1 124.74(19) . . ? N2 C2 C1 123.70(19) . . ? N1 C3 N3 112.97(18) . . ? N1 C3 C4 128.22(18) . . ? N3 C3 C4 118.72(18) . . ? C5 C4 C9 119.13(19) . . ? C5 C4 C3 117.36(19) . . ? C9 C4 C3 123.43(19) . . ? C6 C5 C4 120.8(2) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 119.8(2) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 119.8(2) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.6(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C4 119.8(2) . . ? C8 C9 H9 120.1 . . ? C4 C9 H9 120.1 . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C11 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N6 C11 N5 111.23(17) . . ? N6 C11 C10 124.75(18) . . ? N5 C11 C10 123.97(18) . . ? N4 C12 N6 112.98(18) . . ? N4 C12 C13 127.42(18) . . ? N6 C12 C13 119.59(18) . . ? C18 C13 C14 119.1(2) . . ? C18 C13 C12 123.53(18) . . ? C14 C13 C12 117.37(19) . . ? C15 C14 C13 120.4(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.3(2) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C17 119.8(2) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C18 C17 C16 120.2(2) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C13 120.23(19) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N9 C20 N8 111.28(18) . . ? N9 C20 C19 124.53(19) . . ? N8 C20 C19 124.03(19) . . ? N7 C21 N9 114.25(18) . . ? N7 C21 C22 123.60(18) . . ? N9 C21 C22 122.14(19) . . ? C27 C22 C23 119.4(2) . . ? C27 C22 C21 122.08(19) . . ? C23 C22 C21 118.48(19) . . ? C24 C23 C22 120.5(2) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 119.5(2) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C26 C25 C24 120.9(2) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C25 C26 C27 119.9(2) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C22 C27 C26 119.9(2) . . ? C22 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? N4 Cu1 N4 86.79(9) 2_755 . ? N4 Cu1 N1 170.82(6) 2_755 . ? N4 Cu1 N1 88.73(7) . . ? N4 Cu1 N1 88.73(7) 2_755 2_755 ? N4 Cu1 N1 170.82(6) . 2_755 ? N1 Cu1 N1 96.78(9) . 2_755 ? C3 N1 N2 103.61(15) . . ? C3 N1 Cu1 140.50(14) . . ? N2 N1 Cu1 111.78(12) . . ? C2 N2 N1 108.06(16) . . ? C2 N2 B1 129.84(16) . . ? N1 N2 B1 121.84(15) . . ? C2 N3 C3 103.82(17) . . ? C12 N4 N5 103.59(16) . . ? C12 N4 Cu1 139.90(14) . . ? N5 N4 Cu1 111.32(12) . . ? C11 N5 N4 107.76(16) . . ? C11 N5 B1 130.26(16) . . ? N4 N5 B1 120.98(15) . . ? C11 N6 C12 104.43(16) . . ? C21 N7 N8 103.26(16) . . ? C20 N8 N7 108.30(17) . . ? C20 N8 B1 131.11(17) . . ? N7 N8 B1 120.51(16) . . ? C20 N9 C21 102.87(17) . . ? 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 C3 C4 C5 160.6(2) . . . . ? N3 C3 C4 C5 -23.4(3) . . . . ? N1 C3 C4 C9 -23.0(3) . . . . ? N3 C3 C4 C9 153.1(2) . . . . ? C9 C4 C5 C6 1.1(3) . . . . ? C3 C4 C5 C6 177.78(19) . . . . ? C4 C5 C6 C7 -0.4(3) . . . . ? C5 C6 C7 C8 -0.6(3) . . . . ? C6 C7 C8 C9 0.8(3) . . . . ? C7 C8 C9 C4 0.0(3) . . . . ? C5 C4 C9 C8 -0.9(3) . . . . ? C3 C4 C9 C8 -177.36(19) . . . . ? N4 C12 C13 C18 -18.3(3) . . . . ? N6 C12 C13 C18 160.33(19) . . . . ? N4 C12 C13 C14 163.2(2) . . . . ? N6 C12 C13 C14 -18.2(3) . . . . ? C18 C13 C14 C15 1.9(3) . . . . ? C12 C13 C14 C15 -179.6(2) . . . . ? C13 C14 C15 C16 -0.9(4) . . . . ? C14 C15 C16 C17 -0.3(4) . . . . ? C15 C16 C17 C18 0.6(3) . . . . ? C16 C17 C18 C13 0.3(3) . . . . ? C14 C13 C18 C17 -1.5(3) . . . . ? C12 C13 C18 C17 179.96(19) . . . . ? N7 C21 C22 C27 -2.7(3) . . . . ? N9 C21 C22 C27 177.07(19) . . . . ? N7 C21 C22 C23 176.0(2) . . . . ? N9 C21 C22 C23 -4.2(3) . . . . ? C27 C22 C23 C24 0.8(3) . . . . ? C21 C22 C23 C24 -177.9(2) . . . . ? C22 C23 C24 C25 -0.1(4) . . . . ? C23 C24 C25 C26 -0.6(4) . . . . ? C24 C25 C26 C27 0.6(4) . . . . ? C23 C22 C27 C26 -0.8(3) . . . . ? C21 C22 C27 C26 177.95(19) . . . . ? C25 C26 C27 C22 0.0(3) . . . . ? N3 C3 N1 N2 -1.8(2) . . . . ? C4 C3 N1 N2 174.47(19) . . . . ? N3 C3 N1 Cu1 151.58(17) . . . . ? C4 C3 N1 Cu1 -32.2(3) . . . . ? N4 Cu1 N1 C3 -119.0(2) . . . . ? N1 Cu1 N1 C3 68.4(2) 2_755 . . . ? N4 Cu1 N1 N2 33.03(14) . . . . ? N1 Cu1 N1 N2 -139.62(15) 2_755 . . . ? N3 C2 N2 N1 -1.6(2) . . . . ? C1 C2 N2 N1 175.75(19) . . . . ? N3 C2 N2 B1 172.51(19) . . . . ? C1 C2 N2 B1 -10.1(3) . . . . ? C3 N1 N2 C2 2.0(2) . . . . ? Cu1 N1 N2 C2 -160.12(13) . . . . ? C3 N1 N2 B1 -172.70(17) . . . . ? Cu1 N1 N2 B1 25.2(2) . . . . ? N8 B1 N2 C2 -125.4(2) . . . . ? N5 B1 N2 C2 114.5(2) . . . . ? N8 B1 N2 N1 48.1(2) . . . . ? N5 B1 N2 N1 -72.1(2) . . . . ? N2 C2 N3 C3 0.5(2) . . . . ? C1 C2 N3 C3 -176.8(2) . . . . ? N1 C3 N3 C2 0.8(2) . . . . ? C4 C3 N3 C2 -175.79(18) . . . . ? N6 C12 N4 N5 -0.6(2) . . . . ? C13 C12 N4 N5 178.13(19) . . . . ? N6 C12 N4 Cu1 149.62(17) . . . . ? C13 C12 N4 Cu1 -31.7(4) . . . . ? N4 Cu1 N4 C12 -22.10(19) 2_755 . . . ? N1 Cu1 N4 C12 149.9(2) . . . . ? N4 Cu1 N4 N5 126.67(15) 2_755 . . . ? N1 Cu1 N4 N5 -61.35(13) . . . . ? N6 C11 N5 N4 -0.4(2) . . . . ? C10 C11 N5 N4 176.94(19) . . . . ? N6 C11 N5 B1 168.0(2) . . . . ? C10 C11 N5 B1 -14.7(3) . . . . ? C12 N4 N5 C11 0.6(2) . . . . ? Cu1 N4 N5 C11 -159.35(13) . . . . ? C12 N4 N5 B1 -169.11(18) . . . . ? Cu1 N4 N5 B1 31.0(2) . . . . ? N8 B1 N5 C11 108.9(2) . . . . ? N2 B1 N5 C11 -131.5(2) . . . . ? N8 B1 N5 N4 -84.1(2) . . . . ? N2 B1 N5 N4 35.5(2) . . . . ? N5 C11 N6 C12 0.0(2) . . . . ? C10 C11 N6 C12 -177.3(2) . . . . ? N4 C12 N6 C11 0.4(2) . . . . ? C13 C12 N6 C11 -178.45(18) . . . . ? N9 C21 N7 N8 -1.5(2) . . . . ? C22 C21 N7 N8 178.30(18) . . . . ? N9 C20 N8 N7 -1.7(2) . . . . ? C19 C20 N8 N7 174.02(18) . . . . ? N9 C20 N8 B1 174.87(19) . . . . ? C19 C20 N8 B1 -9.4(3) . . . . ? C21 N7 N8 C20 1.9(2) . . . . ? C21 N7 N8 B1 -175.14(17) . . . . ? N2 B1 N8 C20 100.6(2) . . . . ? N5 B1 N8 C20 -141.5(2) . . . . ? N2 B1 N8 N7 -83.1(2) . . . . ? N5 B1 N8 N7 34.7(2) . . . . ? N8 C20 N9 C21 0.7(2) . . . . ? C19 C20 N9 C21 -174.95(19) . . . . ? N7 C21 N9 C20 0.5(2) . . . . ? C22 C21 N9 C20 -179.28(18) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.436 _refine_diff_density_min -0.590 _refine_diff_density_rms 0.065 data_09mz169_0m _database_code_depnum_ccdc_archive 'CCDC 850804' #TrackingRef '- combined cifs - new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H50 B2 Cu N18 ' _chemical_formula_weight 1036.29 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.177(2) _cell_length_b 10.959(2) _cell_length_c 11.986(2) _cell_angle_alpha 67.639(6) _cell_angle_beta 86.395(5) _cell_angle_gamma 77.426(5) _cell_volume 1206.3(4) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 722 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 31.33 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 539 _exptl_absorpt_coefficient_mu 0.514 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.827 _exptl_absorpt_correction_T_max 0.950 _exptl_absorpt_process_details 'Apex2 v2008.2-4 (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 12510 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 28.28 _reflns_number_total 5928 _reflns_number_gt 4419 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2008.2-4 (Bruker, 2008)' _computing_cell_refinement 'Apex2 v2008.2-4' _computing_data_reduction 'Apex2 v2008.2-4' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^+0.4717P] 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 5928 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1166 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.6079(3) 0.1888(3) 0.1422(2) 0.0223(5) Uani 1 1 d . . . H1 H 0.6448 0.0925 0.1945 0.027 Uiso 1 1 calc R . . C1 C 0.4354(2) 0.0201(2) 0.3467(2) 0.0304(5) Uani 1 1 d . . . H1A H 0.3697 -0.0068 0.4100 0.046 Uiso 1 1 calc R . . H1B H 0.5260 -0.0088 0.3831 0.046 Uiso 1 1 calc R . . H1C H 0.4312 -0.0223 0.2887 0.046 Uiso 1 1 calc R . . C2 C 0.4036(2) 0.1695(2) 0.2835(2) 0.0251(5) Uani 1 1 d . . . C3 C 0.3049(2) 0.3749(2) 0.2272(2) 0.0232(5) Uani 1 1 d . . . C4 C 0.1981(2) 0.4902(2) 0.2260(2) 0.0248(5) Uani 1 1 d . . . C5 C 0.0833(2) 0.4610(3) 0.2928(2) 0.0316(5) Uani 1 1 d . . . H5 H 0.0755 0.3698 0.3338 0.038 Uiso 1 1 calc R . . C6 C -0.0189(3) 0.5641(3) 0.2996(2) 0.0364(6) Uani 1 1 d . . . H6 H -0.0955 0.5430 0.3466 0.044 Uiso 1 1 calc R . . C7 C -0.0109(2) 0.6971(3) 0.2390(2) 0.0319(6) Uani 1 1 d . . . H7 H -0.0809 0.7676 0.2445 0.038 Uiso 1 1 calc R . . C8 C 0.1008(3) 0.7265(3) 0.1700(2) 0.0350(6) Uani 1 1 d . . . H8 H 0.1065 0.8178 0.1260 0.042 Uiso 1 1 calc R . . C9 C 0.2047(2) 0.6226(2) 0.1651(2) 0.0310(5) Uani 1 1 d . . . H9 H 0.2815 0.6439 0.1186 0.037 Uiso 1 1 calc R . . C10 C 0.7081(2) -0.0283(2) 0.0219(2) 0.0294(5) Uani 1 1 d . . . H10A H 0.7148 -0.0796 -0.0303 0.044 Uiso 1 1 calc R . . H10B H 0.6705 -0.0770 0.0994 0.044 Uiso 1 1 calc R . . H10C H 0.7979 -0.0170 0.0356 0.044 Uiso 1 1 calc R . . C11 C 0.6185(2) 0.1069(2) -0.0372(2) 0.0239(5) Uani 1 1 d . . . C12 C 0.4997(2) 0.2799(2) -0.1641(2) 0.0239(5) Uani 1 1 d . . . C13 C 0.4270(2) 0.3700(2) -0.2788(2) 0.0257(5) Uani 1 1 d . . . C14 C 0.3835(2) 0.3133(3) -0.3522(2) 0.0317(5) Uani 1 1 d . . . H14 H 0.3960 0.2180 -0.3259 0.038 Uiso 1 1 calc R . . C15 C 0.3225(3) 0.3945(3) -0.4627(2) 0.0364(6) Uani 1 1 d . . . H15 H 0.2937 0.3549 -0.5123 0.044 Uiso 1 1 calc R . . C16 C 0.3031(2) 0.5332(3) -0.5018(2) 0.0324(6) Uani 1 1 d . . . H16 H 0.2616 0.5889 -0.5783 0.039 Uiso 1 1 calc R . . C17 C 0.3445(2) 0.5905(3) -0.4286(2) 0.0323(6) Uani 1 1 d . . . H17 H 0.3307 0.6858 -0.4549 0.039 Uiso 1 1 calc R . . C18 C 0.4056(2) 0.5097(2) -0.3176(2) 0.0290(5) Uani 1 1 d . . . H18 H 0.4331 0.5497 -0.2677 0.035 Uiso 1 1 calc R . . C19 C 0.8161(2) 0.5923(2) 0.0268(2) 0.0276(5) Uani 1 1 d . . . H19A H 0.8560 0.6150 0.0868 0.041 Uiso 1 1 calc R . . H19B H 0.7296 0.6548 -0.0023 0.041 Uiso 1 1 calc R . . H19C H 0.8769 0.5997 -0.0411 0.041 Uiso 1 1 calc R . . C20 C 0.7943(2) 0.4515(2) 0.0832(2) 0.0231(5) Uani 1 1 d . . . C21 C 0.8349(2) 0.2421(2) 0.1868(2) 0.0240(5) Uani 1 1 d . . . C22 C 0.9012(2) 0.1074(2) 0.2693(2) 0.0261(5) Uani 1 1 d . . . C23 C 1.0352(2) 0.0564(3) 0.2523(2) 0.0315(5) Uani 1 1 d . . . H23 H 1.0825 0.1074 0.1863 0.038 Uiso 1 1 calc R . . C24 C 1.1002(2) -0.0701(3) 0.3327(2) 0.0340(6) Uani 1 1 d . . . H24 H 1.1915 -0.1056 0.3209 0.041 Uiso 1 1 calc R . . C25 C 1.0323(3) -0.1431(3) 0.4286(2) 0.0361(6) Uani 1 1 d . . . H25 H 1.0766 -0.2297 0.4822 0.043 Uiso 1 1 calc R . . C26 C 0.9006(3) -0.0920(2) 0.4482(2) 0.0324(6) Uani 1 1 d . . . H26 H 0.8551 -0.1421 0.5162 0.039 Uiso 1 1 calc R . . C27 C 0.8349(2) 0.0321(2) 0.3685(2) 0.0292(5) Uani 1 1 d . . . H27 H 0.7436 0.0666 0.3814 0.035 Uiso 1 1 calc R . . Cu1 Cu 0.5000 0.5000 0.0000 0.02162(12) Uani 1 2 d S . . N1 N 0.41304(18) 0.37519(18) 0.15704(16) 0.0222(4) Uani 1 1 d . . . N2 N 0.47655(18) 0.24059(18) 0.19518(16) 0.0219(4) Uani 1 1 d . . . N3 N 0.29675(19) 0.24983(19) 0.30560(17) 0.0262(4) Uani 1 1 d . . . N4 N 0.50413(18) 0.31278(18) -0.06892(16) 0.0225(4) Uani 1 1 d . . . N5 N 0.58093(18) 0.19821(17) 0.01393(16) 0.0204(4) Uani 1 1 d . . . N6 N 0.56898(19) 0.1540(2) -0.14837(17) 0.0271(4) Uani 1 1 d . . . N7 N 0.70900(18) 0.27515(18) 0.14139(16) 0.0215(4) Uani 1 1 d . . . N8 N 0.68194(18) 0.41195(18) 0.07448(16) 0.0218(4) Uani 1 1 d . . . N9 N 0.89078(19) 0.34949(19) 0.15105(17) 0.0259(4) 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 B1 0.0224(12) 0.0212(12) 0.0227(13) -0.0088(10) -0.0003(10) -0.0023(10) C1 0.0331(13) 0.0273(12) 0.0305(13) -0.0098(10) 0.0049(10) -0.0086(10) C2 0.0273(12) 0.0254(12) 0.0238(12) -0.0103(10) 0.0026(9) -0.0069(10) C3 0.0233(11) 0.0270(12) 0.0212(11) -0.0123(10) -0.0018(9) -0.0026(9) C4 0.0264(12) 0.0280(12) 0.0230(12) -0.0138(10) -0.0033(9) -0.0029(10) C5 0.0282(12) 0.0322(13) 0.0320(13) -0.0102(11) 0.0007(10) -0.0049(10) C6 0.0267(12) 0.0409(15) 0.0378(15) -0.0136(12) 0.0057(11) -0.0032(11) C7 0.0288(12) 0.0320(13) 0.0345(14) -0.0159(11) -0.0012(11) 0.0012(10) C8 0.0392(14) 0.0273(13) 0.0362(14) -0.0122(11) 0.0033(12) -0.0023(11) C9 0.0317(13) 0.0314(13) 0.0314(13) -0.0140(11) 0.0076(10) -0.0078(10) C10 0.0336(13) 0.0224(12) 0.0289(13) -0.0098(10) -0.0003(10) 0.0014(10) C11 0.0246(11) 0.0218(11) 0.0258(12) -0.0109(10) 0.0027(9) -0.0030(9) C12 0.0235(11) 0.0264(12) 0.0228(12) -0.0114(10) 0.0018(9) -0.0040(9) C13 0.0226(11) 0.0322(13) 0.0200(11) -0.0105(10) 0.0008(9) -0.0003(10) C14 0.0323(13) 0.0334(13) 0.0298(13) -0.0172(11) 0.0000(10) 0.0023(11) C15 0.0331(13) 0.0512(17) 0.0301(14) -0.0253(13) -0.0038(11) 0.0004(12) C16 0.0281(13) 0.0396(15) 0.0228(12) -0.0104(11) -0.0017(10) 0.0051(11) C17 0.0297(13) 0.0299(13) 0.0294(13) -0.0067(11) -0.0035(10) 0.0026(10) C18 0.0288(12) 0.0304(13) 0.0266(12) -0.0111(10) -0.0031(10) -0.0020(10) C19 0.0280(12) 0.0254(12) 0.0293(13) -0.0096(10) -0.0030(10) -0.0055(10) C20 0.0211(11) 0.0265(12) 0.0214(11) -0.0103(9) 0.0002(9) -0.0023(9) C21 0.0233(11) 0.0244(11) 0.0237(12) -0.0098(9) -0.0004(9) -0.0022(9) C22 0.0261(12) 0.0249(12) 0.0265(12) -0.0099(10) -0.0048(9) -0.0018(9) C23 0.0271(12) 0.0328(13) 0.0353(14) -0.0141(11) 0.0031(10) -0.0062(10) C24 0.0241(12) 0.0322(13) 0.0473(16) -0.0204(12) -0.0047(11) 0.0022(10) C25 0.0366(14) 0.0255(13) 0.0407(15) -0.0094(12) -0.0125(12) 0.0028(11) C26 0.0394(14) 0.0264(12) 0.0283(13) -0.0064(10) -0.0039(11) -0.0063(11) C27 0.0270(12) 0.0302(13) 0.0264(12) -0.0095(10) -0.0006(10) 0.0001(10) Cu1 0.0198(2) 0.0209(2) 0.0215(2) -0.00644(16) -0.00066(15) -0.00162(15) N1 0.0247(9) 0.0205(9) 0.0212(9) -0.0097(8) -0.0021(8) 0.0000(8) N2 0.0253(9) 0.0199(9) 0.0204(9) -0.0079(8) 0.0003(8) -0.0037(8) N3 0.0295(10) 0.0251(10) 0.0237(10) -0.0100(8) 0.0024(8) -0.0045(8) N4 0.0220(9) 0.0214(9) 0.0209(9) -0.0066(8) 0.0000(7) -0.0005(7) N5 0.0214(9) 0.0177(9) 0.0197(9) -0.0056(7) -0.0006(7) -0.0014(7) N6 0.0291(10) 0.0274(10) 0.0240(10) -0.0119(8) -0.0005(8) 0.0002(8) N7 0.0210(9) 0.0180(9) 0.0229(10) -0.0062(8) -0.0017(7) -0.0012(7) N8 0.0226(9) 0.0194(9) 0.0226(9) -0.0077(8) 0.0002(8) -0.0030(7) N9 0.0229(10) 0.0252(10) 0.0279(10) -0.0089(8) -0.0007(8) -0.0033(8) _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 1.533(3) . ? B1 N7 1.539(3) . ? B1 N5 1.540(3) . ? B1 H1 1.0000 . ? C1 C2 1.489(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N3 1.324(3) . ? C2 N2 1.343(3) . ? C3 N1 1.342(3) . ? C3 N3 1.352(3) . ? C3 C4 1.473(3) . ? C4 C9 1.368(3) . ? C4 C5 1.400(3) . ? C5 C6 1.383(3) . ? C5 H5 0.9500 . ? C6 C7 1.377(4) . ? C6 H6 0.9500 . ? C7 C8 1.385(4) . ? C7 H7 0.9500 . ? C8 C9 1.392(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.491(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N6 1.321(3) . ? C11 N5 1.339(3) . ? C12 N4 1.326(3) . ? C12 N6 1.354(3) . ? C12 C13 1.480(3) . ? C13 C18 1.390(3) . ? C13 C14 1.394(3) . ? C14 C15 1.378(3) . ? C14 H14 0.9500 . ? C15 C16 1.381(4) . ? C15 H15 0.9500 . ? C16 C17 1.387(4) . ? C16 H16 0.9500 . ? C17 C18 1.382(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.491(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 N8 1.331(3) . ? C20 N9 1.343(3) . ? C21 N9 1.330(3) . ? C21 N7 1.343(3) . ? C21 C22 1.467(3) . ? C22 C23 1.390(3) . ? C22 C27 1.395(3) . ? C23 C24 1.397(3) . ? C23 H23 0.9500 . ? C24 C25 1.371(4) . ? C24 H24 0.9500 . ? C25 C26 1.378(4) . ? C25 H25 0.9500 . ? C26 C27 1.380(3) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? Cu1 N8 1.9826(18) . ? Cu1 N8 1.9826(18) 2_665 ? Cu1 N1 2.1345(19) . ? Cu1 N1 2.1345(19) 2_665 ? Cu1 N4 2.4783(19) . ? Cu1 N4 2.4783(19) 2_665 ? N1 N2 1.383(2) . ? N4 N5 1.377(2) . ? N7 N8 1.378(2) . ? 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 N7 107.86(18) . . ? N2 B1 N5 109.88(18) . . ? N7 B1 N5 111.17(18) . . ? N2 B1 H1 109.3 . . ? N7 B1 H1 109.3 . . ? N5 B1 H1 109.3 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N3 C2 N2 110.9(2) . . ? N3 C2 C1 123.9(2) . . ? N2 C2 C1 125.1(2) . . ? N1 C3 N3 112.9(2) . . ? N1 C3 C4 128.3(2) . . ? N3 C3 C4 118.8(2) . . ? C9 C4 C5 118.5(2) . . ? C9 C4 C3 124.4(2) . . ? C5 C4 C3 117.2(2) . . ? C6 C5 C4 120.4(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 120.8(2) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 119.0(2) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? C7 C8 C9 120.2(2) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C4 C9 C8 121.2(2) . . ? C4 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C11 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N6 C11 N5 111.03(19) . . ? N6 C11 C10 124.4(2) . . ? N5 C11 C10 124.6(2) . . ? N4 C12 N6 114.0(2) . . ? N4 C12 C13 124.5(2) . . ? N6 C12 C13 121.5(2) . . ? C18 C13 C14 119.1(2) . . ? C18 C13 C12 121.8(2) . . ? C14 C13 C12 119.1(2) . . ? C15 C14 C13 120.4(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.4(2) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C17 119.5(2) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C18 C17 C16 120.4(2) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C13 120.2(2) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N8 C20 N9 112.8(2) . . ? N8 C20 C19 125.7(2) . . ? N9 C20 C19 121.5(2) . . ? N9 C21 N7 111.00(19) . . ? N9 C21 C22 123.8(2) . . ? N7 C21 C22 125.1(2) . . ? C23 C22 C27 119.1(2) . . ? C23 C22 C21 119.5(2) . . ? C27 C22 C21 121.3(2) . . ? C22 C23 C24 119.8(2) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C25 C24 C23 120.1(2) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 120.6(2) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 C27 119.8(2) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C26 C27 C22 120.6(2) . . ? C26 C27 H27 119.7 . . ? C22 C27 H27 119.7 . . ? N8 Cu1 N8 180.0 . 2_665 ? N8 Cu1 N1 89.86(7) . . ? N8 Cu1 N1 90.14(7) 2_665 . ? N8 Cu1 N1 90.14(7) . 2_665 ? N8 Cu1 N1 89.86(7) 2_665 2_665 ? N1 Cu1 N1 180.0 . 2_665 ? N8 Cu1 N4 90.03(7) . . ? N8 Cu1 N4 89.97(7) 2_665 . ? N1 Cu1 N4 83.39(7) . . ? N1 Cu1 N4 96.61(7) 2_665 . ? N8 Cu1 N4 89.97(7) . 2_665 ? N8 Cu1 N4 90.03(7) 2_665 2_665 ? N1 Cu1 N4 96.61(7) . 2_665 ? N1 Cu1 N4 83.39(7) 2_665 2_665 ? N4 Cu1 N4 180.0 . 2_665 ? C3 N1 N2 103.68(17) . . ? C3 N1 Cu1 142.50(15) . . ? N2 N1 Cu1 113.03(13) . . ? C2 N2 N1 108.01(17) . . ? C2 N2 B1 128.39(19) . . ? N1 N2 B1 123.60(18) . . ? C2 N3 C3 104.47(19) . . ? C12 N4 N5 103.12(17) . . ? C12 N4 Cu1 145.20(15) . . ? N5 N4 Cu1 107.22(12) . . ? C11 N5 N4 108.35(17) . . ? C11 N5 B1 130.42(19) . . ? N4 N5 B1 121.21(18) . . ? C11 N6 C12 103.44(19) . . ? C21 N7 N8 107.13(17) . . ? C21 N7 B1 132.01(19) . . ? N8 N7 B1 120.50(18) . . ? C20 N8 N7 104.70(17) . . ? C20 N8 Cu1 136.45(16) . . ? N7 N8 Cu1 118.78(13) . . ? C21 N9 C20 104.36(19) . . ? 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 C3 C4 C9 -12.0(4) . . . . ? N3 C3 C4 C9 169.5(2) . . . . ? N1 C3 C4 C5 168.6(2) . . . . ? N3 C3 C4 C5 -9.9(3) . . . . ? C9 C4 C5 C6 -1.9(4) . . . . ? C3 C4 C5 C6 177.5(2) . . . . ? C4 C5 C6 C7 1.3(4) . . . . ? C5 C6 C7 C8 0.6(4) . . . . ? C6 C7 C8 C9 -1.8(4) . . . . ? C5 C4 C9 C8 0.7(4) . . . . ? C3 C4 C9 C8 -178.7(2) . . . . ? C7 C8 C9 C4 1.1(4) . . . . ? N4 C12 C13 C18 27.8(3) . . . . ? N6 C12 C13 C18 -152.1(2) . . . . ? N4 C12 C13 C14 -154.8(2) . . . . ? N6 C12 C13 C14 25.4(3) . . . . ? C18 C13 C14 C15 1.3(4) . . . . ? C12 C13 C14 C15 -176.2(2) . . . . ? C13 C14 C15 C16 -0.4(4) . . . . ? C14 C15 C16 C17 -0.5(4) . . . . ? C15 C16 C17 C18 0.5(4) . . . . ? C16 C17 C18 C13 0.5(4) . . . . ? C14 C13 C18 C17 -1.3(3) . . . . ? C12 C13 C18 C17 176.1(2) . . . . ? N9 C21 C22 C23 -44.9(3) . . . . ? N7 C21 C22 C23 138.1(2) . . . . ? N9 C21 C22 C27 131.6(3) . . . . ? N7 C21 C22 C27 -45.4(3) . . . . ? C27 C22 C23 C24 1.6(4) . . . . ? C21 C22 C23 C24 178.1(2) . . . . ? C22 C23 C24 C25 -0.6(4) . . . . ? C23 C24 C25 C26 -1.1(4) . . . . ? C24 C25 C26 C27 1.9(4) . . . . ? C25 C26 C27 C22 -1.0(4) . . . . ? C23 C22 C27 C26 -0.8(4) . . . . ? C21 C22 C27 C26 -177.2(2) . . . . ? N3 C3 N1 N2 -0.2(2) . . . . ? C4 C3 N1 N2 -178.8(2) . . . . ? N3 C3 N1 Cu1 167.96(18) . . . . ? C4 C3 N1 Cu1 -10.6(4) . . . . ? N8 Cu1 N1 C3 145.4(2) . . . . ? N8 Cu1 N1 C3 -34.6(2) 2_665 . . . ? N4 Cu1 N1 C3 -124.6(2) . . . . ? N4 Cu1 N1 C3 55.4(2) 2_665 . . . ? N8 Cu1 N1 N2 -47.14(14) . . . . ? N8 Cu1 N1 N2 132.86(14) 2_665 . . . ? N4 Cu1 N1 N2 42.91(14) . . . . ? N4 Cu1 N1 N2 -137.09(14) 2_665 . . . ? N3 C2 N2 N1 -0.3(3) . . . . ? C1 C2 N2 N1 178.2(2) . . . . ? N3 C2 N2 B1 179.3(2) . . . . ? C1 C2 N2 B1 -2.2(4) . . . . ? C3 N1 N2 C2 0.3(2) . . . . ? Cu1 N1 N2 C2 -171.90(14) . . . . ? C3 N1 N2 B1 -179.31(19) . . . . ? Cu1 N1 N2 B1 8.5(2) . . . . ? N7 B1 N2 C2 -130.0(2) . . . . ? N5 B1 N2 C2 108.6(2) . . . . ? N7 B1 N2 N1 49.5(3) . . . . ? N5 B1 N2 N1 -71.8(2) . . . . ? N2 C2 N3 C3 0.2(3) . . . . ? C1 C2 N3 C3 -178.4(2) . . . . ? N1 C3 N3 C2 0.0(3) . . . . ? C4 C3 N3 C2 178.8(2) . . . . ? N6 C12 N4 N5 -0.7(2) . . . . ? C13 C12 N4 N5 179.4(2) . . . . ? N6 C12 N4 Cu1 149.6(2) . . . . ? C13 C12 N4 Cu1 -30.3(4) . . . . ? N8 Cu1 N4 C12 -119.0(3) . . . . ? N8 Cu1 N4 C12 61.0(3) 2_665 . . . ? N1 Cu1 N4 C12 151.2(3) . . . . ? N1 Cu1 N4 C12 -28.8(3) 2_665 . . . ? N8 Cu1 N4 N5 30.61(13) . . . . ? N8 Cu1 N4 N5 -149.39(13) 2_665 . . . ? N1 Cu1 N4 N5 -59.25(13) . . . . ? N1 Cu1 N4 N5 120.75(13) 2_665 . . . ? N6 C11 N5 N4 -1.1(2) . . . . ? C10 C11 N5 N4 177.1(2) . . . . ? N6 C11 N5 B1 177.2(2) . . . . ? C10 C11 N5 B1 -4.7(4) . . . . ? C12 N4 N5 C11 1.0(2) . . . . ? Cu1 N4 N5 C11 -161.74(14) . . . . ? C12 N4 N5 B1 -177.46(19) . . . . ? Cu1 N4 N5 B1 19.8(2) . . . . ? N2 B1 N5 C11 -132.1(2) . . . . ? N7 B1 N5 C11 108.6(3) . . . . ? N2 B1 N5 N4 46.0(3) . . . . ? N7 B1 N5 N4 -73.3(2) . . . . ? N5 C11 N6 C12 0.6(2) . . . . ? C10 C11 N6 C12 -177.5(2) . . . . ? N4 C12 N6 C11 0.1(3) . . . . ? C13 C12 N6 C11 180.0(2) . . . . ? N9 C21 N7 N8 -1.1(2) . . . . ? C22 C21 N7 N8 176.3(2) . . . . ? N9 C21 N7 B1 171.9(2) . . . . ? C22 C21 N7 B1 -10.7(4) . . . . ? N2 B1 N7 C21 125.8(2) . . . . ? N5 B1 N7 C21 -113.7(3) . . . . ? N2 B1 N7 N8 -62.0(2) . . . . ? N5 B1 N7 N8 58.6(3) . . . . ? N9 C20 N8 N7 -0.1(2) . . . . ? C19 C20 N8 N7 -179.5(2) . . . . ? N9 C20 N8 Cu1 176.63(16) . . . . ? C19 C20 N8 Cu1 -2.8(4) . . . . ? C21 N7 N8 C20 0.7(2) . . . . ? B1 N7 N8 C20 -173.30(19) . . . . ? C21 N7 N8 Cu1 -176.75(14) . . . . ? B1 N7 N8 Cu1 9.3(2) . . . . ? N1 Cu1 N8 C20 -137.9(2) . . . . ? N1 Cu1 N8 C20 42.1(2) 2_665 . . . ? N4 Cu1 N8 C20 138.8(2) . . . . ? N4 Cu1 N8 C20 -41.2(2) 2_665 . . . ? N1 Cu1 N8 N7 38.53(15) . . . . ? N1 Cu1 N8 N7 -141.47(15) 2_665 . . . ? N4 Cu1 N8 N7 -44.86(15) . . . . ? N4 Cu1 N8 N7 135.14(15) 2_665 . . . ? N7 C21 N9 C20 1.0(3) . . . . ? C22 C21 N9 C20 -176.5(2) . . . . ? N8 C20 N9 C21 -0.5(3) . . . . ? C19 C20 N9 C21 178.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.472 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.066 data_09mz087_0m _database_code_depnum_ccdc_archive 'CCDC 850805' #TrackingRef '- combined cifs - new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H50 B2 Co N18' _chemical_formula_weight 1031.67 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z+1/2' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'y+2/3, x+1/3, -z+5/6' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'y+1/3, x+2/3, -z+7/6' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z-1/2' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-y+2/3, -x+1/3, z-1/6' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-y+1/3, -x+2/3, z+1/6' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' _cell_length_a 13.8978(15) _cell_length_b 13.8978 _cell_length_c 43.178(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7222.5(12) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1416 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 29.20 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3222 _exptl_absorpt_coefficient_mu 0.418 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.790 _exptl_absorpt_correction_T_max 0.871 _exptl_absorpt_process_details 'Apex2 v2008.2-4 (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 6495 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -57 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 28.27 _reflns_number_total 1997 _reflns_number_gt 1613 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2008.2-4 (Bruker, 2008)' _computing_cell_refinement 'Apex2 v2008.2-4' _computing_data_reduction 'Apex2 v2008.2-4' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0506P)^2^+7.4199P] 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 1997 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1049 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.6667 0.3333 0.01080(8) 0.0191(6) Uani 1 3 d S . . H1 H 0.6667 0.3333 -0.0124 0.023 Uiso 1 3 calc SR . . C1 C 0.67843(16) 0.13866(15) -0.02433(4) 0.0274(4) Uani 1 1 d . . . H1A H 0.7598 0.1804 -0.0246 0.041 Uiso 1 1 calc R . . H1B H 0.6497 0.1761 -0.0375 0.041 Uiso 1 1 calc R . . H1C H 0.6520 0.0633 -0.0321 0.041 Uiso 1 1 calc R . . C2 C 0.63861(14) 0.13280(14) 0.00793(4) 0.0220(4) Uani 1 1 d . . . C3 C 0.58076(13) 0.07955(14) 0.05343(4) 0.0205(4) Uani 1 1 d . . . C4 C 0.53419(14) 0.00302(14) 0.07996(4) 0.0221(4) Uani 1 1 d . . . C5 C 0.53737(15) -0.09626(15) 0.07866(4) 0.0276(4) Uani 1 1 d . . . H5 H 0.5672 -0.1124 0.0609 0.033 Uiso 1 1 calc R . . C6 C 0.49743(16) -0.17042(15) 0.10297(5) 0.0331(5) Uani 1 1 d . . . H6 H 0.5001 -0.2373 0.1020 0.040 Uiso 1 1 calc R . . C7 C 0.45340(16) -0.14760(16) 0.12886(5) 0.0317(4) Uani 1 1 d . . . H7 H 0.4273 -0.1981 0.1458 0.038 Uiso 1 1 calc R . . C8 C 0.44750(15) -0.05127(15) 0.13011(4) 0.0272(4) Uani 1 1 d . . . H8 H 0.4162 -0.0362 0.1477 0.033 Uiso 1 1 calc R . . C9 C 0.48717(14) 0.02335(14) 0.10571(4) 0.0236(4) Uani 1 1 d . . . H9 H 0.4822 0.0890 0.1066 0.028 Uiso 1 1 calc R . . N1 N 0.64183(11) 0.21894(11) 0.02298(3) 0.0195(3) Uani 1 1 d . . . N2 N 0.60658(11) 0.18664(11) 0.05296(3) 0.0186(3) Uani 1 1 d . . . N3 N 0.60027(12) 0.04430(12) 0.02624(3) 0.0239(3) Uani 1 1 d . . . Co1 Co 0.6667 0.3333 0.0833 0.01701(16) Uani 1 6 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0195(9) 0.0195(9) 0.0184(15) 0.000 0.000 0.0097(5) C1 0.0304(10) 0.0243(9) 0.0271(10) -0.0025(7) 0.0019(8) 0.0133(8) C2 0.0193(8) 0.0202(8) 0.0258(9) -0.0026(7) -0.0022(7) 0.0093(7) C3 0.0182(8) 0.0179(8) 0.0248(9) -0.0021(7) -0.0023(7) 0.0086(7) C4 0.0184(8) 0.0180(8) 0.0271(9) 0.0001(7) -0.0052(7) 0.0069(7) C5 0.0280(9) 0.0213(9) 0.0332(10) -0.0006(8) -0.0004(8) 0.0122(8) C6 0.0317(10) 0.0198(9) 0.0473(12) 0.0061(8) -0.0009(9) 0.0125(8) C7 0.0252(9) 0.0271(10) 0.0365(11) 0.0125(8) -0.0007(8) 0.0084(8) C8 0.0214(9) 0.0275(9) 0.0274(9) 0.0029(8) 0.0000(7) 0.0084(7) C9 0.0207(8) 0.0197(8) 0.0281(9) -0.0011(7) -0.0038(7) 0.0083(7) N1 0.0180(7) 0.0196(7) 0.0197(7) -0.0010(6) -0.0005(5) 0.0084(6) N2 0.0167(7) 0.0183(7) 0.0201(7) 0.0014(5) -0.0005(5) 0.0083(6) N3 0.0232(7) 0.0208(7) 0.0265(8) -0.0019(6) -0.0009(6) 0.0100(6) Co1 0.01543(19) 0.01543(19) 0.0202(3) 0.000 0.000 0.00772(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 B1 N1 1.5409(18) . ? B1 N1 1.5410(18) 2_655 ? B1 N1 1.5410(18) 3_665 ? B1 H1 1.0000 . ? C1 C2 1.486(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N3 1.329(2) . ? C2 N1 1.343(2) . ? C3 N2 1.346(2) . ? C3 N3 1.351(2) . ? C3 C4 1.474(2) . ? C4 C9 1.388(3) . ? C4 C5 1.404(2) . ? C5 C6 1.378(3) . ? C5 H5 0.9500 . ? C6 C7 1.385(3) . ? C6 H6 0.9500 . ? C7 C8 1.383(3) . ? C7 H7 0.9500 . ? C8 C9 1.385(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? N1 N2 1.3776(19) . ? N2 Co1 2.2070(14) . ? Co1 N2 2.2069(14) 2_655 ? Co1 N2 2.2069(14) 3_665 ? Co1 N2 2.2069(14) 16_544 ? Co1 N2 2.2069(14) 17_554 ? Co1 N2 2.2070(14) 18_654 ? 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 N1 108.98(13) . 2_655 ? N1 B1 N1 108.98(13) . 3_665 ? N1 B1 N1 108.98(13) 2_655 3_665 ? N1 B1 H1 110.0 . . ? N1 B1 H1 110.0 2_655 . ? N1 B1 H1 110.0 3_665 . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N3 C2 N1 110.87(15) . . ? N3 C2 C1 125.06(16) . . ? N1 C2 C1 124.00(16) . . ? N2 C3 N3 113.41(15) . . ? N2 C3 C4 125.99(15) . . ? N3 C3 C4 120.60(15) . . ? C9 C4 C5 118.76(17) . . ? C9 C4 C3 123.85(15) . . ? C5 C4 C3 117.39(16) . . ? C6 C5 C4 120.40(18) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 120.14(18) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 120.02(18) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.06(18) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C4 120.58(17) . . ? C8 C9 H9 119.7 . . ? C4 C9 H9 119.7 . . ? C2 N1 N2 108.44(14) . . ? C2 N1 B1 130.16(17) . . ? N2 N1 B1 121.10(16) . . ? C3 N2 N1 103.25(13) . . ? C3 N2 Co1 141.39(11) . . ? N1 N2 Co1 110.41(9) . . ? C2 N3 C3 103.99(14) . . ? N2 Co1 N2 88.31(5) 2_655 3_665 ? N2 Co1 N2 170.42(7) 2_655 16_544 ? N2 Co1 N2 85.46(7) 3_665 16_544 ? N2 Co1 N2 85.46(7) 2_655 17_554 ? N2 Co1 N2 98.76(7) 3_665 17_554 ? N2 Co1 N2 88.31(5) 16_544 17_554 ? N2 Co1 N2 98.76(7) 2_655 18_654 ? N2 Co1 N2 170.42(7) 3_665 18_654 ? N2 Co1 N2 88.30(5) 16_544 18_654 ? N2 Co1 N2 88.30(5) 17_554 18_654 ? N2 Co1 N2 88.31(5) 2_655 . ? N2 Co1 N2 88.31(5) 3_665 . ? N2 Co1 N2 98.76(7) 16_544 . ? N2 Co1 N2 170.42(7) 17_554 . ? N2 Co1 N2 85.46(7) 18_654 . ? 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 C3 C4 C9 15.3(3) . . . . ? N3 C3 C4 C9 -163.81(16) . . . . ? N2 C3 C4 C5 -165.17(16) . . . . ? N3 C3 C4 C5 15.7(2) . . . . ? C9 C4 C5 C6 -1.9(3) . . . . ? C3 C4 C5 C6 178.60(16) . . . . ? C4 C5 C6 C7 0.2(3) . . . . ? C5 C6 C7 C8 1.2(3) . . . . ? C6 C7 C8 C9 -1.0(3) . . . . ? C7 C8 C9 C4 -0.7(3) . . . . ? C5 C4 C9 C8 2.1(3) . . . . ? C3 C4 C9 C8 -178.41(16) . . . . ? N3 C2 N1 N2 1.61(19) . . . . ? C1 C2 N1 N2 -175.42(15) . . . . ? N3 C2 N1 B1 -172.13(12) . . . . ? C1 C2 N1 B1 10.9(3) . . . . ? N1 B1 N1 C2 -109.1(2) 2_655 . . . ? N1 B1 N1 C2 132.1(2) 3_665 . . . ? N1 B1 N1 N2 77.85(16) 2_655 . . . ? N1 B1 N1 N2 -41.0(2) 3_665 . . . ? N3 C3 N2 N1 1.68(18) . . . . ? C4 C3 N2 N1 -177.53(15) . . . . ? N3 C3 N2 Co1 -148.67(14) . . . . ? C4 C3 N2 Co1 32.1(3) . . . . ? C2 N1 N2 C3 -1.93(17) . . . . ? B1 N1 N2 C3 172.48(12) . . . . ? C2 N1 N2 Co1 158.84(11) . . . . ? B1 N1 N2 Co1 -26.75(15) . . . . ? N1 C2 N3 C3 -0.54(18) . . . . ? C1 C2 N3 C3 176.44(17) . . . . ? N2 C3 N3 C2 -0.76(19) . . . . ? C4 C3 N3 C2 178.49(15) . . . . ? C3 N2 Co1 N2 118.5(2) . . . 2_655 ? N1 N2 Co1 N2 -30.54(9) . . . 2_655 ? C3 N2 Co1 N2 -153.11(19) . . . 3_665 ? N1 N2 Co1 N2 57.82(8) . . . 3_665 ? C3 N2 Co1 N2 -67.97(17) . . . 16_544 ? N1 N2 Co1 N2 142.96(11) . . . 16_544 ? C3 N2 Co1 N2 19.61(15) . . . 18_654 ? N1 N2 Co1 N2 -129.46(12) . . . 18_654 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.303 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.058 data_11mz052_0m _database_code_depnum_ccdc_archive 'CCDC 850806' #TrackingRef '- combined cifs - new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H42 B2 Cl4 Co N18' _chemical_formula_weight 829.13 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5094(16) _cell_length_b 10.5276(17) _cell_length_c 19.314(4) _cell_angle_alpha 101.173(3) _cell_angle_beta 96.336(3) _cell_angle_gamma 114.198(2) _cell_volume 1868.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6797 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 30.82 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 858 _exptl_absorpt_coefficient_mu 0.793 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6832 _exptl_absorpt_correction_T_max 0.7463 _exptl_absorpt_process_details 'Apex2 v2009.7-0 (Bruker, 2009)' _exptl_special_details ; Both solvate methylene chloride molecules are disordered. One over two positions with an occupancy ratio of 0.873(4) to 0.127(4), the other over three positions with occupancies of 0.773(2), 0.117(3) and 0.109(3). C-Cl bonds and intramolecular Cl...Cl distances in the disordered molecules were restrained to be similar. Overlapping atoms were constrained to be identical. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 42736 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.10 _diffrn_reflns_theta_max 31.51 _reflns_number_total 11342 _reflns_number_gt 9398 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2009.7-0 (Bruker, 2009)' _computing_cell_refinement 'Apex2 v2009.7-0' _computing_data_reduction 'Apex2 v2009.7-0' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0895P)^2^+2.5320P] 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 11342 _refine_ls_number_parameters 521 _refine_ls_number_restraints 32 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1777 _refine_ls_wR_factor_gt 0.1648 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.069 _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 0.0317(3) 0.6120(3) 0.17884(14) 0.0207(4) Uani 1 1 d . . . H1 H -0.0303 0.6514 0.1572 0.025 Uiso 1 1 calc R . . B2 B 0.4303(2) 0.3546(3) 0.31788(13) 0.0178(4) Uani 1 1 d . . . H2 H 0.4913 0.3142 0.3395 0.021 Uiso 1 1 calc R . . C1 C 0.5598(2) 0.8106(3) 0.25053(15) 0.0268(5) Uani 1 1 d . . . H1A H 0.5495 0.7293 0.2707 0.040 Uiso 1 1 calc R . . H1B H 0.6166 0.9015 0.2878 0.040 Uiso 1 1 calc R . . H1C H 0.6077 0.8081 0.2099 0.040 Uiso 1 1 calc R . . C2 C 0.4163(2) 0.8001(2) 0.22489(12) 0.0213(4) Uani 1 1 d . . . C3 C 0.2544(3) 0.8502(3) 0.18144(13) 0.0245(4) Uani 1 1 d . . . C4 C 0.1780(3) 0.9254(3) 0.15117(15) 0.0334(6) Uani 1 1 d . . . H4A H 0.2459 1.0253 0.1554 0.050 Uiso 1 1 calc R . . H4B H 0.1040 0.9250 0.1780 0.050 Uiso 1 1 calc R . . H4C H 0.1337 0.8754 0.1002 0.050 Uiso 1 1 calc R . . C5 C 0.0840(3) 0.1640(3) 0.09019(14) 0.0287(5) Uani 1 1 d . . . H5A H 0.1723 0.2018 0.1267 0.043 Uiso 1 1 calc R . . H5B H 0.1027 0.1382 0.0421 0.043 Uiso 1 1 calc R . . H5C H 0.0116 0.0781 0.0996 0.043 Uiso 1 1 calc R . . C6 C 0.0317(2) 0.2759(3) 0.09344(13) 0.0224(4) Uani 1 1 d . . . C7 C -0.0888(3) 0.3840(3) 0.06662(12) 0.0243(4) Uani 1 1 d . . . C8 C -0.1937(3) 0.4227(3) 0.02939(15) 0.0345(6) Uani 1 1 d . . . H8A H -0.2421 0.3527 -0.0177 0.052 Uiso 1 1 calc R . . H8B H -0.1439 0.5195 0.0225 0.052 Uiso 1 1 calc R . . H8C H -0.2642 0.4215 0.0588 0.052 Uiso 1 1 calc R . . C9 C 0.0675(3) 0.4735(3) 0.40996(13) 0.0265(5) Uani 1 1 d . . . H9A H 0.1340 0.4351 0.3956 0.040 Uiso 1 1 calc R . . H9B H -0.0156 0.3971 0.4195 0.040 Uiso 1 1 calc R . . H9C H 0.1153 0.5535 0.4538 0.040 Uiso 1 1 calc R . . C10 C 0.0202(2) 0.5264(2) 0.35084(12) 0.0208(4) Uani 1 1 d . . . C11 C -0.0872(2) 0.6165(3) 0.29168(13) 0.0223(4) Uani 1 1 d . . . C12 C -0.1788(3) 0.6847(3) 0.27047(16) 0.0296(5) Uani 1 1 d . . . H12A H -0.2490 0.6730 0.3011 0.044 Uiso 1 1 calc R . . H12B H -0.2285 0.6384 0.2198 0.044 Uiso 1 1 calc R . . H12C H -0.1193 0.7877 0.2764 0.044 Uiso 1 1 calc R . . C13 C 0.2781(3) 0.0628(3) 0.36695(15) 0.0286(5) Uani 1 1 d . . . H13A H 0.2077 -0.0293 0.3719 0.043 Uiso 1 1 calc R . . H13B H 0.3314 0.1268 0.4149 0.043 Uiso 1 1 calc R . . H13C H 0.3443 0.0456 0.3388 0.043 Uiso 1 1 calc R . . C14 C 0.2037(3) 0.1315(2) 0.32925(12) 0.0214(4) Uani 1 1 d . . . C15 C 0.0446(2) 0.1748(2) 0.27651(12) 0.0206(4) Uani 1 1 d . . . C16 C -0.0982(2) 0.1600(3) 0.24488(14) 0.0264(5) Uani 1 1 d . . . H16A H -0.0861 0.2386 0.2221 0.040 Uiso 1 1 calc R . . H16B H -0.1514 0.1647 0.2831 0.040 Uiso 1 1 calc R . . H16C H -0.1510 0.0671 0.2085 0.040 Uiso 1 1 calc R . . C17 C 0.6704(2) 0.5517(3) 0.46188(13) 0.0246(4) Uani 1 1 d . . . H17A H 0.7371 0.5494 0.4306 0.037 Uiso 1 1 calc R . . H17B H 0.6218 0.4566 0.4709 0.037 Uiso 1 1 calc R . . H17C H 0.7230 0.6242 0.5079 0.037 Uiso 1 1 calc R . . C18 C 0.5630(2) 0.5894(2) 0.42598(11) 0.0185(4) Uani 1 1 d . . . C19 C 0.4394(2) 0.6971(2) 0.40143(12) 0.0196(4) Uani 1 1 d . . . C20 C 0.3840(3) 0.8073(3) 0.40656(14) 0.0260(5) Uani 1 1 d . . . H20A H 0.2982 0.7713 0.3686 0.039 Uiso 1 1 calc R . . H20B H 0.4570 0.8967 0.4005 0.039 Uiso 1 1 calc R . . H20C H 0.3603 0.8263 0.4540 0.039 Uiso 1 1 calc R . . C21 C 0.6291(3) 0.2670(3) 0.22273(15) 0.0271(5) Uani 1 1 d . . . H21A H 0.6906 0.2663 0.1882 0.041 Uiso 1 1 calc R . . H21B H 0.5672 0.1676 0.2228 0.041 Uiso 1 1 calc R . . H21C H 0.6884 0.3206 0.2712 0.041 Uiso 1 1 calc R . . C22 C 0.5399(2) 0.3377(2) 0.20167(13) 0.0213(4) Uani 1 1 d . . . C23 C 0.4420(2) 0.4390(2) 0.14529(12) 0.0205(4) Uani 1 1 d . . . C24 C 0.4023(3) 0.5014(3) 0.08834(13) 0.0264(5) Uani 1 1 d . . . H24A H 0.3395 0.5440 0.1038 0.040 Uiso 1 1 calc R . . H24B H 0.3526 0.4251 0.0433 0.040 Uiso 1 1 calc R . . H24C H 0.4888 0.5763 0.0805 0.040 Uiso 1 1 calc R . . C25 C 0.8250(4) 0.0471(4) 0.4343(2) 0.0498(11) Uani 0.873(4) 1 d PD A 1 H25A H 0.7631 -0.0445 0.4446 0.060 Uiso 0.873(4) 1 calc PR A 1 H25B H 0.8728 0.0249 0.3955 0.060 Uiso 0.873(4) 1 calc PR A 1 C26 C 0.6623(5) 0.8962(5) 0.0260(2) 0.0453(10) Uani 0.773(2) 1 d PD B 1 H26A H 0.7304 0.9857 0.0164 0.054 Uiso 0.773(2) 1 calc PR B 1 H26B H 0.6033 0.8277 -0.0208 0.054 Uiso 0.773(2) 1 calc PR B 1 Cl1 Cl 0.71772(15) 0.13585(15) 0.40596(7) 0.0507(4) Uani 0.873(4) 1 d PD A 1 Cl2 Cl 0.95151(16) 0.16402(13) 0.51160(6) 0.0521(4) Uani 0.873(4) 1 d PD A 1 Cl3 Cl 0.55233(13) 0.93559(13) 0.07960(6) 0.0490(3) Uani 0.773(2) 1 d PD B 1 Cl4 Cl 0.75807(16) 0.81908(16) 0.07081(8) 0.0499(3) Uani 0.773(2) 1 d PD B 1 Co1 Co 0.23233(3) 0.48462(3) 0.248156(15) 0.01587(9) Uani 1 1 d . . . N1 N 0.2958(2) 0.6850(2) 0.21996(10) 0.0192(3) Uani 1 1 d . . . N2 N 0.1907(2) 0.7181(2) 0.19097(10) 0.0194(3) Uani 1 1 d . . . N3 N 0.3957(2) 0.9052(2) 0.20227(12) 0.0282(4) Uani 1 1 d . . . N4 N 0.0832(2) 0.3952(2) 0.14692(10) 0.0197(3) Uani 1 1 d . . . N5 N 0.0047(2) 0.4661(2) 0.12917(10) 0.0198(3) Uani 1 1 d . . . N6 N -0.0751(2) 0.2635(2) 0.04261(11) 0.0276(4) Uani 1 1 d . . . N7 N 0.0714(2) 0.5304(2) 0.29114(10) 0.0195(3) Uani 1 1 d . . . N8 N 0.0007(2) 0.5888(2) 0.25277(10) 0.0194(3) Uani 1 1 d . . . N9 N -0.0790(2) 0.5777(2) 0.35329(11) 0.0251(4) Uani 1 1 d . . . N10 N 0.1668(2) 0.2825(2) 0.27521(10) 0.0188(3) Uani 1 1 d . . . N11 N 0.2704(2) 0.25390(19) 0.30939(10) 0.0178(3) Uani 1 1 d . . . N12 N 0.0616(2) 0.0787(2) 0.30946(11) 0.0234(4) Uani 1 1 d . . . N13 N 0.3829(2) 0.5746(2) 0.34948(10) 0.0180(3) Uani 1 1 d . . . N14 N 0.46361(19) 0.50447(19) 0.36575(10) 0.0171(3) Uani 1 1 d . . . N15 N 0.5513(2) 0.7115(2) 0.44949(10) 0.0211(4) Uani 1 1 d . . . N16 N 0.3931(2) 0.4377(2) 0.20547(10) 0.0185(3) Uani 1 1 d . . . N17 N 0.4571(2) 0.3719(2) 0.24222(10) 0.0181(3) Uani 1 1 d . . . N18 N 0.5326(2) 0.3774(2) 0.14025(11) 0.0234(4) Uani 1 1 d . . . C26B C 0.598(2) 0.8443(19) 0.0482(13) 0.0453(10) Uani 0.117(3) 1 d PD C 2 H26C H 0.5328 0.8498 0.0806 0.054 Uiso 0.117(3) 1 calc PR C 2 H26D H 0.5404 0.7704 0.0026 0.054 Uiso 0.117(3) 1 calc PR C 2 Cl3B Cl 0.6869(8) 1.0120(8) 0.0303(4) 0.052(2) Uani 0.117(3) 1 d PD C 2 Cl4B Cl 0.7206(11) 0.7946(10) 0.0887(5) 0.0499(3) Uani 0.117(3) 1 d PD C 2 C26C C 0.665(2) 0.936(3) 0.0740(10) 0.0453(10) Uani 0.109(3) 1 d PD D 3 H26E H 0.6086 0.9429 0.1113 0.054 Uiso 0.109(3) 1 calc PR D 3 H26F H 0.7278 1.0358 0.0725 0.054 Uiso 0.109(3) 1 calc PR D 3 Cl3C Cl 0.5504(14) 0.8410(13) -0.0095(6) 0.080(4) Uani 0.109(3) 1 d PD D 3 Cl4C Cl 0.7683(11) 0.8509(12) 0.0964(6) 0.0499(3) Uani 0.109(3) 1 d PD D 3 C25B C 0.913(2) 0.067(3) 0.4226(9) 0.0498(11) Uani 0.127(4) 1 d PD A 2 H25C H 0.9769 0.1174 0.3927 0.060 Uiso 0.127(4) 1 calc PR A 2 H25D H 0.8824 -0.0385 0.4052 0.060 Uiso 0.127(4) 1 calc PR A 2 Cl1B Cl 0.7582(11) 0.1078(12) 0.4218(6) 0.061(2) Uani 0.127(4) 1 d PD A 2 Cl2B Cl 1.0005(11) 0.1359(10) 0.5197(4) 0.0521(4) Uani 0.127(4) 1 d PD A 2 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 0.0215(11) 0.0254(11) 0.0216(11) 0.0095(9) 0.0041(9) 0.0153(10) B2 0.0163(10) 0.0189(10) 0.0211(10) 0.0078(8) 0.0011(8) 0.0103(8) C1 0.0174(10) 0.0268(11) 0.0353(13) 0.0119(9) 0.0060(9) 0.0071(9) C2 0.0221(10) 0.0206(10) 0.0230(10) 0.0088(8) 0.0059(8) 0.0096(8) C3 0.0307(12) 0.0209(10) 0.0243(10) 0.0089(8) 0.0017(9) 0.0134(9) C4 0.0422(15) 0.0232(11) 0.0361(13) 0.0125(10) -0.0032(11) 0.0166(11) C5 0.0315(12) 0.0225(11) 0.0313(12) 0.0038(9) 0.0003(10) 0.0144(10) C6 0.0209(10) 0.0228(10) 0.0231(10) 0.0060(8) 0.0018(8) 0.0100(8) C7 0.0231(10) 0.0340(12) 0.0189(10) 0.0079(9) 0.0018(8) 0.0160(10) C8 0.0315(13) 0.0512(17) 0.0256(12) 0.0088(11) -0.0039(10) 0.0260(13) C9 0.0302(12) 0.0309(12) 0.0231(11) 0.0129(9) 0.0088(9) 0.0146(10) C10 0.0202(9) 0.0218(10) 0.0212(10) 0.0068(8) 0.0046(8) 0.0096(8) C11 0.0181(9) 0.0234(10) 0.0280(11) 0.0064(8) 0.0055(8) 0.0115(8) C12 0.0237(11) 0.0326(12) 0.0416(14) 0.0119(11) 0.0093(10) 0.0197(10) C13 0.0306(12) 0.0227(11) 0.0344(13) 0.0150(9) -0.0011(10) 0.0123(10) C14 0.0245(10) 0.0167(9) 0.0235(10) 0.0084(8) 0.0015(8) 0.0092(8) C15 0.0198(9) 0.0196(9) 0.0226(10) 0.0076(8) 0.0023(8) 0.0087(8) C16 0.0181(10) 0.0294(12) 0.0310(12) 0.0113(9) 0.0029(9) 0.0090(9) C17 0.0167(9) 0.0349(12) 0.0232(10) 0.0101(9) 0.0012(8) 0.0122(9) C18 0.0151(8) 0.0237(10) 0.0169(9) 0.0084(7) 0.0036(7) 0.0075(8) C19 0.0203(9) 0.0176(9) 0.0219(10) 0.0076(7) 0.0053(8) 0.0082(8) C20 0.0295(11) 0.0214(10) 0.0306(12) 0.0063(9) 0.0079(9) 0.0146(9) C21 0.0245(11) 0.0264(11) 0.0394(13) 0.0112(10) 0.0089(10) 0.0182(10) C22 0.0185(9) 0.0193(9) 0.0273(11) 0.0053(8) 0.0045(8) 0.0098(8) C23 0.0205(9) 0.0219(10) 0.0211(10) 0.0062(8) 0.0038(8) 0.0111(8) C24 0.0321(12) 0.0343(12) 0.0201(10) 0.0122(9) 0.0068(9) 0.0192(11) C25 0.042(2) 0.0357(18) 0.0391(18) -0.0047(14) 0.0122(16) -0.0080(16) C26 0.047(2) 0.039(2) 0.0316(18) -0.0017(15) 0.0201(17) 0.0041(18) Cl1 0.0423(6) 0.0510(6) 0.0407(6) 0.0071(4) 0.0123(5) 0.0047(5) Cl2 0.0505(7) 0.0424(5) 0.0416(5) 0.0054(4) 0.0059(5) 0.0031(5) Cl3 0.0506(6) 0.0514(6) 0.0362(5) 0.0042(4) 0.0173(4) 0.0156(5) Cl4 0.0478(6) 0.0390(6) 0.0431(7) -0.0021(5) 0.0168(6) 0.0043(5) Co1 0.01562(14) 0.01759(15) 0.01857(15) 0.00792(10) 0.00231(10) 0.01025(11) N1 0.0188(8) 0.0217(8) 0.0238(9) 0.0109(7) 0.0056(7) 0.0129(7) N2 0.0218(9) 0.0206(8) 0.0217(8) 0.0104(7) 0.0040(7) 0.0132(7) N3 0.0306(11) 0.0195(9) 0.0315(11) 0.0107(8) 0.0013(8) 0.0078(8) N4 0.0205(8) 0.0207(8) 0.0215(8) 0.0079(7) 0.0021(7) 0.0121(7) N5 0.0185(8) 0.0256(9) 0.0203(8) 0.0091(7) 0.0019(7) 0.0135(7) N6 0.0269(10) 0.0327(11) 0.0230(9) 0.0042(8) 0.0002(8) 0.0156(9) N7 0.0190(8) 0.0233(9) 0.0223(8) 0.0109(7) 0.0043(7) 0.0132(7) N8 0.0193(8) 0.0236(9) 0.0232(9) 0.0102(7) 0.0055(7) 0.0150(7) N9 0.0242(9) 0.0280(10) 0.0271(10) 0.0077(8) 0.0094(8) 0.0142(8) N10 0.0164(8) 0.0199(8) 0.0233(9) 0.0088(7) 0.0015(7) 0.0104(7) N11 0.0180(8) 0.0170(8) 0.0218(8) 0.0081(6) 0.0012(6) 0.0103(7) N12 0.0233(9) 0.0196(9) 0.0266(9) 0.0096(7) 0.0029(7) 0.0077(7) N13 0.0187(8) 0.0184(8) 0.0202(8) 0.0078(6) 0.0028(7) 0.0104(7) N14 0.0155(7) 0.0185(8) 0.0196(8) 0.0074(6) 0.0017(6) 0.0091(7) N15 0.0190(8) 0.0221(9) 0.0205(8) 0.0056(7) 0.0030(7) 0.0077(7) N16 0.0186(8) 0.0213(8) 0.0194(8) 0.0073(7) 0.0020(6) 0.0122(7) N17 0.0181(8) 0.0184(8) 0.0212(8) 0.0064(6) 0.0019(7) 0.0112(7) N18 0.0239(9) 0.0258(9) 0.0264(9) 0.0085(7) 0.0073(8) 0.0154(8) C26B 0.047(2) 0.039(2) 0.0316(18) -0.0017(15) 0.0201(17) 0.0041(18) Cl3B 0.036(3) 0.050(4) 0.055(4) 0.011(3) 0.006(3) 0.006(3) Cl4B 0.0478(6) 0.0390(6) 0.0431(7) -0.0021(5) 0.0168(6) 0.0043(5) C26C 0.047(2) 0.039(2) 0.0316(18) -0.0017(15) 0.0201(17) 0.0041(18) Cl3C 0.095(9) 0.069(7) 0.072(7) 0.015(6) 0.026(7) 0.030(7) Cl4C 0.0478(6) 0.0390(6) 0.0431(7) -0.0021(5) 0.0168(6) 0.0043(5) C25B 0.042(2) 0.0357(18) 0.0391(18) -0.0047(14) 0.0122(16) -0.0080(16) Cl1B 0.055(5) 0.078(6) 0.065(6) 0.031(5) 0.017(4) 0.039(5) Cl2B 0.0505(7) 0.0424(5) 0.0416(5) 0.0054(4) 0.0059(5) 0.0031(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 N5 1.539(3) . ? B1 N8 1.542(3) . ? B1 N2 1.542(3) . ? B1 H1 1.0000 . ? B2 N14 1.542(3) . ? B2 N11 1.544(3) . ? B2 N17 1.549(3) . ? B2 H2 1.0000 . ? C1 C2 1.486(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N1 1.324(3) . ? C2 N3 1.351(3) . ? C3 N3 1.332(3) . ? C3 N2 1.334(3) . ? C3 C4 1.487(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.485(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 N4 1.324(3) . ? C6 N6 1.352(3) . ? C7 N6 1.336(3) . ? C7 N5 1.345(3) . ? C7 C8 1.484(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.486(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 N7 1.326(3) . ? C10 N9 1.357(3) . ? C11 N9 1.336(3) . ? C11 N8 1.338(3) . ? C11 C12 1.485(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.486(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N12 1.340(3) . ? C14 N11 1.345(3) . ? C15 N10 1.327(3) . ? C15 N12 1.354(3) . ? C15 C16 1.489(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.487(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 N15 1.338(3) . ? C18 N14 1.344(3) . ? C19 N13 1.328(3) . ? C19 N15 1.352(3) . ? C19 C20 1.488(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.484(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 N18 1.337(3) . ? C22 N17 1.341(3) . ? C23 N16 1.322(3) . ? C23 N18 1.356(3) . ? C23 C24 1.490(3) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 Cl2 1.738(4) . ? C25 Cl1 1.836(5) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 Cl3 1.752(4) . ? C26 Cl4 1.780(5) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? Co1 N1 2.1362(18) . ? Co1 N4 2.1372(19) . ? Co1 N10 2.1407(19) . ? Co1 N13 2.1446(19) . ? Co1 N7 2.1459(19) . ? Co1 N16 2.1476(19) . ? N1 N2 1.381(2) . ? N4 N5 1.377(2) . ? N7 N8 1.382(2) . ? N10 N11 1.378(2) . ? N13 N14 1.382(2) . ? N16 N17 1.380(2) . ? C26B Cl4B 1.740(15) . ? C26B Cl3B 1.751(14) . ? C26B H26C 0.9900 . ? C26B H26D 0.9900 . ? C26C Cl3C 1.736(14) . ? C26C Cl4C 1.741(15) . ? C26C H26E 0.9900 . ? C26C H26F 0.9900 . ? C25B Cl1B 1.847(15) . ? C25B Cl2B 1.853(14) . ? C25B H25C 0.9900 . ? C25B H25D 0.9900 . ? 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 N5 B1 N8 108.35(18) . . ? N5 B1 N2 108.96(18) . . ? N8 B1 N2 107.61(18) . . ? N5 B1 H1 110.6 . . ? N8 B1 H1 110.6 . . ? N2 B1 H1 110.6 . . ? N14 B2 N11 108.52(17) . . ? N14 B2 N17 107.82(17) . . ? N11 B2 N17 108.01(17) . . ? N14 B2 H2 110.8 . . ? N11 B2 H2 110.8 . . ? N17 B2 H2 110.8 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N3 113.2(2) . . ? N1 C2 C1 123.3(2) . . ? N3 C2 C1 123.4(2) . . ? N3 C3 N2 110.9(2) . . ? N3 C3 C4 124.6(2) . . ? N2 C3 C4 124.5(2) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C6 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N4 C6 N6 113.9(2) . . ? N4 C6 C5 123.2(2) . . ? N6 C6 C5 122.8(2) . . ? N6 C7 N5 111.2(2) . . ? N6 C7 C8 124.6(2) . . ? N5 C7 C8 124.2(2) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N7 C10 N9 113.2(2) . . ? N7 C10 C9 123.8(2) . . ? N9 C10 C9 123.0(2) . . ? N9 C11 N8 110.9(2) . . ? N9 C11 C12 124.3(2) . . ? N8 C11 C12 124.8(2) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N12 C14 N11 111.11(19) . . ? N12 C14 C13 124.6(2) . . ? N11 C14 C13 124.3(2) . . ? N10 C15 N12 113.5(2) . . ? N10 C15 C16 123.6(2) . . ? N12 C15 C16 122.9(2) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C18 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N15 C18 N14 110.79(19) . . ? N15 C18 C17 124.7(2) . . ? N14 C18 C17 124.5(2) . . ? N13 C19 N15 113.44(19) . . ? N13 C19 C20 123.2(2) . . ? N15 C19 C20 123.3(2) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N18 C22 N17 110.90(19) . . ? N18 C22 C21 124.6(2) . . ? N17 C22 C21 124.5(2) . . ? N16 C23 N18 113.3(2) . . ? N16 C23 C24 123.8(2) . . ? N18 C23 C24 122.9(2) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? Cl2 C25 Cl1 107.9(2) . . ? Cl2 C25 H25A 110.1 . . ? Cl1 C25 H25A 110.1 . . ? Cl2 C25 H25B 110.1 . . ? Cl1 C25 H25B 110.1 . . ? H25A C25 H25B 108.4 . . ? Cl3 C26 Cl4 110.1(2) . . ? Cl3 C26 H26A 109.6 . . ? Cl4 C26 H26A 109.6 . . ? Cl3 C26 H26B 109.6 . . ? Cl4 C26 H26B 109.6 . . ? H26A C26 H26B 108.2 . . ? N1 Co1 N4 85.02(7) . . ? N1 Co1 N10 179.30(7) . . ? N4 Co1 N10 94.28(7) . . ? N1 Co1 N13 94.86(7) . . ? N4 Co1 N13 179.72(8) . . ? N10 Co1 N13 85.84(7) . . ? N1 Co1 N7 86.05(7) . . ? N4 Co1 N7 85.69(7) . . ? N10 Co1 N7 93.88(7) . . ? N13 Co1 N7 94.55(7) . . ? N1 Co1 N16 94.31(7) . . ? N4 Co1 N16 94.41(7) . . ? N10 Co1 N16 85.76(7) . . ? N13 Co1 N16 85.34(7) . . ? N7 Co1 N16 179.63(7) . . ? C2 N1 N2 104.14(17) . . ? C2 N1 Co1 137.39(15) . . ? N2 N1 Co1 118.40(14) . . ? C3 N2 N1 107.84(19) . . ? C3 N2 B1 131.52(19) . . ? N1 N2 B1 120.55(17) . . ? C3 N3 C2 103.9(2) . . ? C6 N4 N5 104.14(18) . . ? C6 N4 Co1 137.11(15) . . ? N5 N4 Co1 118.51(14) . . ? C7 N5 N4 107.53(19) . . ? C7 N5 B1 131.94(19) . . ? N4 N5 B1 120.52(17) . . ? C7 N6 C6 103.2(2) . . ? C10 N7 N8 104.24(17) . . ? C10 N7 Co1 137.21(15) . . ? N8 N7 Co1 118.41(14) . . ? C11 N8 N7 107.89(18) . . ? C11 N8 B1 131.87(19) . . ? N7 N8 B1 120.24(17) . . ? C11 N9 C10 103.79(19) . . ? C15 N10 N11 104.43(17) . . ? C15 N10 Co1 136.81(15) . . ? N11 N10 Co1 118.13(13) . . ? C14 N11 N10 107.52(18) . . ? C14 N11 B2 131.86(18) . . ? N10 N11 B2 120.62(17) . . ? C14 N12 C15 103.39(18) . . ? C19 N13 N14 104.26(17) . . ? C19 N13 Co1 136.97(15) . . ? N14 N13 Co1 118.01(13) . . ? C18 N14 N13 107.69(17) . . ? C18 N14 B2 131.76(18) . . ? N13 N14 B2 120.55(17) . . ? C18 N15 C19 103.81(18) . . ? C23 N16 N17 104.53(17) . . ? C23 N16 Co1 136.81(15) . . ? N17 N16 Co1 118.10(14) . . ? C22 N17 N16 107.62(18) . . ? C22 N17 B2 132.02(18) . . ? N16 N17 B2 120.32(17) . . ? C22 N18 C23 103.68(19) . . ? Cl4B C26B Cl3B 110.3(11) . . ? Cl4B C26B H26C 109.6 . . ? Cl3B C26B H26C 109.6 . . ? Cl4B C26B H26D 109.6 . . ? Cl3B C26B H26D 109.6 . . ? H26C C26B H26D 108.1 . . ? Cl3C C26C Cl4C 110.2(11) . . ? Cl3C C26C H26E 109.6 . . ? Cl4C C26C H26E 109.6 . . ? Cl3C C26C H26F 109.6 . . ? Cl4C C26C H26F 109.6 . . ? H26E C26C H26F 108.1 . . ? Cl1B C25B Cl2B 101.8(9) . . ? Cl1B C25B H25C 111.4 . . ? Cl2B C25B H25C 111.4 . . ? Cl1B C25B H25D 111.4 . . ? Cl2B C25B H25D 111.4 . . ? H25C C25B H25D 109.3 . . ? 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 C2 N1 N2 1.0(3) . . . . ? C1 C2 N1 N2 -177.1(2) . . . . ? N3 C2 N1 Co1 -175.67(17) . . . . ? C1 C2 N1 Co1 6.2(4) . . . . ? N4 Co1 N1 C2 -139.9(2) . . . . ? N13 Co1 N1 C2 39.9(2) . . . . ? N7 Co1 N1 C2 134.1(2) . . . . ? N16 Co1 N1 C2 -45.8(2) . . . . ? N4 Co1 N1 N2 43.75(16) . . . . ? N13 Co1 N1 N2 -136.50(15) . . . . ? N7 Co1 N1 N2 -42.26(16) . . . . ? N16 Co1 N1 N2 137.82(15) . . . . ? N3 C3 N2 N1 0.4(3) . . . . ? C4 C3 N2 N1 179.9(2) . . . . ? N3 C3 N2 B1 177.0(2) . . . . ? C4 C3 N2 B1 -3.4(4) . . . . ? C2 N1 N2 C3 -0.8(2) . . . . ? Co1 N1 N2 C3 176.65(15) . . . . ? C2 N1 N2 B1 -177.9(2) . . . . ? Co1 N1 N2 B1 -0.5(3) . . . . ? N5 B1 N2 C3 126.0(2) . . . . ? N8 B1 N2 C3 -116.7(3) . . . . ? N5 B1 N2 N1 -57.7(2) . . . . ? N8 B1 N2 N1 59.6(2) . . . . ? N2 C3 N3 C2 0.3(3) . . . . ? C4 C3 N3 C2 -179.3(2) . . . . ? N1 C2 N3 C3 -0.8(3) . . . . ? C1 C2 N3 C3 177.3(2) . . . . ? N6 C6 N4 N5 -0.5(3) . . . . ? C5 C6 N4 N5 -179.2(2) . . . . ? N6 C6 N4 Co1 173.55(17) . . . . ? C5 C6 N4 Co1 -5.1(4) . . . . ? N1 Co1 N4 C6 140.7(2) . . . . ? N10 Co1 N4 C6 -39.3(2) . . . . ? N7 Co1 N4 C6 -132.9(2) . . . . ? N16 Co1 N4 C6 46.7(2) . . . . ? N1 Co1 N4 N5 -45.85(16) . . . . ? N10 Co1 N4 N5 134.13(16) . . . . ? N7 Co1 N4 N5 40.55(16) . . . . ? N16 Co1 N4 N5 -139.81(16) . . . . ? N6 C7 N5 N4 -0.2(3) . . . . ? C8 C7 N5 N4 179.7(2) . . . . ? N6 C7 N5 B1 -179.3(2) . . . . ? C8 C7 N5 B1 0.6(4) . . . . ? C6 N4 N5 C7 0.4(2) . . . . ? Co1 N4 N5 C7 -175.02(15) . . . . ? C6 N4 N5 B1 179.6(2) . . . . ? Co1 N4 N5 B1 4.2(3) . . . . ? N8 B1 N5 C7 117.6(3) . . . . ? N2 B1 N5 C7 -125.6(2) . . . . ? N8 B1 N5 N4 -61.4(3) . . . . ? N2 B1 N5 N4 55.4(3) . . . . ? N5 C7 N6 C6 -0.2(3) . . . . ? C8 C7 N6 C6 180.0(2) . . . . ? N4 C6 N6 C7 0.4(3) . . . . ? C5 C6 N6 C7 179.1(2) . . . . ? N9 C10 N7 N8 0.3(3) . . . . ? C9 C10 N7 N8 -178.8(2) . . . . ? N9 C10 N7 Co1 175.57(17) . . . . ? C9 C10 N7 Co1 -3.5(4) . . . . ? N1 Co1 N7 C10 -134.0(2) . . . . ? N4 Co1 N7 C10 140.7(2) . . . . ? N10 Co1 N7 C10 46.7(2) . . . . ? N13 Co1 N7 C10 -39.5(2) . . . . ? N1 Co1 N7 N8 40.79(16) . . . . ? N4 Co1 N7 N8 -44.50(16) . . . . ? N10 Co1 N7 N8 -138.51(16) . . . . ? N13 Co1 N7 N8 135.36(16) . . . . ? N9 C11 N8 N7 -0.7(3) . . . . ? C12 C11 N8 N7 177.8(2) . . . . ? N9 C11 N8 B1 179.9(2) . . . . ? C12 C11 N8 B1 -1.7(4) . . . . ? C10 N7 N8 C11 0.2(2) . . . . ? Co1 N7 N8 C11 -176.13(15) . . . . ? C10 N7 N8 B1 179.8(2) . . . . ? Co1 N7 N8 B1 3.4(3) . . . . ? N5 B1 N8 C11 -124.1(2) . . . . ? N2 B1 N8 C11 118.2(3) . . . . ? N5 B1 N8 N7 56.5(3) . . . . ? N2 B1 N8 N7 -61.2(3) . . . . ? N8 C11 N9 C10 0.8(3) . . . . ? C12 C11 N9 C10 -177.7(2) . . . . ? N7 C10 N9 C11 -0.7(3) . . . . ? C9 C10 N9 C11 178.4(2) . . . . ? N12 C15 N10 N11 0.3(3) . . . . ? C16 C15 N10 N11 -179.6(2) . . . . ? N12 C15 N10 Co1 -169.90(17) . . . . ? C16 C15 N10 Co1 10.2(4) . . . . ? N4 Co1 N10 C15 -49.2(2) . . . . ? N13 Co1 N10 C15 131.0(2) . . . . ? N7 Co1 N10 C15 36.7(2) . . . . ? N16 Co1 N10 C15 -143.3(2) . . . . ? N4 Co1 N10 N11 141.55(15) . . . . ? N13 Co1 N10 N11 -38.20(15) . . . . ? N7 Co1 N10 N11 -132.49(15) . . . . ? N16 Co1 N10 N11 47.43(15) . . . . ? N12 C14 N11 N10 0.2(3) . . . . ? C13 C14 N11 N10 179.1(2) . . . . ? N12 C14 N11 B2 -178.9(2) . . . . ? C13 C14 N11 B2 0.0(4) . . . . ? C15 N10 N11 C14 -0.3(2) . . . . ? Co1 N10 N11 C14 172.09(15) . . . . ? C15 N10 N11 B2 178.92(19) . . . . ? Co1 N10 N11 B2 -8.7(2) . . . . ? N14 B2 N11 C14 -117.5(2) . . . . ? N17 B2 N11 C14 125.9(2) . . . . ? N14 B2 N11 N10 63.5(2) . . . . ? N17 B2 N11 N10 -53.1(2) . . . . ? N11 C14 N12 C15 -0.1(3) . . . . ? C13 C14 N12 C15 -179.0(2) . . . . ? N10 C15 N12 C14 -0.2(3) . . . . ? C16 C15 N12 C14 179.8(2) . . . . ? N15 C19 N13 N14 0.6(2) . . . . ? C20 C19 N13 N14 -178.9(2) . . . . ? N15 C19 N13 Co1 -168.60(16) . . . . ? C20 C19 N13 Co1 11.9(4) . . . . ? N1 Co1 N13 C19 35.6(2) . . . . ? N10 Co1 N13 C19 -144.4(2) . . . . ? N7 Co1 N13 C19 -50.8(2) . . . . ? N16 Co1 N13 C19 129.5(2) . . . . ? N1 Co1 N13 N14 -132.56(15) . . . . ? N10 Co1 N13 N14 47.45(15) . . . . ? N7 Co1 N13 N14 141.03(15) . . . . ? N16 Co1 N13 N14 -38.62(15) . . . . ? N15 C18 N14 N13 -0.3(2) . . . . ? C17 C18 N14 N13 179.2(2) . . . . ? N15 C18 N14 B2 -179.7(2) . . . . ? C17 C18 N14 B2 -0.2(4) . . . . ? C19 N13 N14 C18 -0.2(2) . . . . ? Co1 N13 N14 C18 171.49(14) . . . . ? C19 N13 N14 B2 179.29(19) . . . . ? Co1 N13 N14 B2 -9.0(2) . . . . ? N11 B2 N14 C18 127.0(2) . . . . ? N17 B2 N14 C18 -116.3(2) . . . . ? N11 B2 N14 N13 -52.4(2) . . . . ? N17 B2 N14 N13 64.4(2) . . . . ? N14 C18 N15 C19 0.6(2) . . . . ? C17 C18 N15 C19 -178.8(2) . . . . ? N13 C19 N15 C18 -0.8(3) . . . . ? C20 C19 N15 C18 178.7(2) . . . . ? N18 C23 N16 N17 0.5(3) . . . . ? C24 C23 N16 N17 -179.5(2) . . . . ? N18 C23 N16 Co1 -170.24(17) . . . . ? C24 C23 N16 Co1 9.7(4) . . . . ? N1 Co1 N16 C23 -47.5(2) . . . . ? N4 Co1 N16 C23 37.8(2) . . . . ? N10 Co1 N16 C23 131.8(2) . . . . ? N13 Co1 N16 C23 -142.0(2) . . . . ? N1 Co1 N16 N17 142.71(15) . . . . ? N4 Co1 N16 N17 -131.97(15) . . . . ? N10 Co1 N16 N17 -37.99(15) . . . . ? N13 Co1 N16 N17 48.17(15) . . . . ? N18 C22 N17 N16 -0.2(3) . . . . ? C21 C22 N17 N16 179.0(2) . . . . ? N18 C22 N17 B2 -177.9(2) . . . . ? C21 C22 N17 B2 1.2(4) . . . . ? C23 N16 N17 C22 -0.2(2) . . . . ? Co1 N16 N17 C22 172.66(14) . . . . ? C23 N16 N17 B2 177.89(19) . . . . ? Co1 N16 N17 B2 -9.3(2) . . . . ? N14 B2 N17 C22 124.6(2) . . . . ? N11 B2 N17 C22 -118.3(2) . . . . ? N14 B2 N17 N16 -52.9(2) . . . . ? N11 B2 N17 N16 64.2(2) . . . . ? N17 C22 N18 C23 0.5(3) . . . . ? C21 C22 N18 C23 -178.7(2) . . . . ? N16 C23 N18 C22 -0.6(3) . . . . ? C24 C23 N18 C22 179.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.360 _refine_diff_density_min -1.252 _refine_diff_density_rms 0.107 data_09mz076_0m _database_code_depnum_ccdc_archive 'CCDC 850807' #TrackingRef '- combined cifs - new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H50 B2 Fe N18' _chemical_formula_weight 1028.59 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z+1/2' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'y+2/3, x+1/3, -z+5/6' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'y+1/3, x+2/3, -z+7/6' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z-1/2' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-y+2/3, -x+1/3, z-1/6' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-y+1/3, -x+2/3, z+1/6' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' _cell_length_a 13.9034(4) _cell_length_b 13.9034(4) _cell_length_c 43.507(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7283.4(5) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2715 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 31.31 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.43 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3216 _exptl_absorpt_coefficient_mu 0.371 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.755 _exptl_absorpt_correction_T_max 0.853 _exptl_absorpt_process_details 'Apex2 v2008.2-4 (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 6475 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 57 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.27 _reflns_number_total 2010 _reflns_number_gt 1734 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2008.2-4 (Bruker, 2008)' _computing_cell_refinement 'Apex2 v2008.2-4' _computing_data_reduction 'Apex2 v2008.2-4' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0452P)^2^+10.3700P] 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 2010 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0910 _refine_ls_wR_factor_gt 0.0858 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.6667 0.3333 0.01135(6) 0.0162(5) Uani 1 3 d S . . H1 H 0.6667 0.3333 -0.0116 0.019 Uiso 1 3 calc SR . . C1 C 0.46018(12) 0.13937(12) -0.02389(3) 0.0228(3) Uani 1 1 d . . . H1A H 0.4114 0.0643 -0.0318 0.034 Uiso 1 1 calc R . . H1B H 0.5264 0.1772 -0.0369 0.034 Uiso 1 1 calc R . . H1C H 0.4206 0.1811 -0.0241 0.034 Uiso 1 1 calc R . . C2 C 0.49388(11) 0.13256(11) 0.00819(3) 0.0181(3) Uani 1 1 d . . . C3 C 0.49749(11) 0.07762(11) 0.05313(3) 0.0174(3) Uani 1 1 d . . . C4 C 0.46693(11) 0.00067(11) 0.07947(3) 0.0184(3) Uani 1 1 d . . . C5 C 0.36457(12) -0.09804(12) 0.07820(3) 0.0237(3) Uani 1 1 d . . . H5 H 0.3188 -0.1144 0.0605 0.028 Uiso 1 1 calc R . . C6 C 0.32960(13) -0.17211(12) 0.10257(4) 0.0288(3) Uani 1 1 d . . . H6 H 0.2599 -0.2388 0.1016 0.035 Uiso 1 1 calc R . . C7 C 0.39618(13) -0.14909(12) 0.12835(4) 0.0273(3) Uani 1 1 d . . . H7 H 0.3714 -0.1993 0.1452 0.033 Uiso 1 1 calc R . . C8 C 0.49901(13) -0.05278(12) 0.12957(3) 0.0235(3) Uani 1 1 d . . . H8 H 0.5452 -0.0378 0.1471 0.028 Uiso 1 1 calc R . . C9 C 0.53458(12) 0.02188(11) 0.10512(3) 0.0201(3) Uani 1 1 d . . . H9 H 0.6052 0.0875 0.1059 0.024 Uiso 1 1 calc R . . Fe1 Fe 0.6667 0.3333 0.0833 0.01394(13) Uani 1 6 d S . . N1 N 0.57946(9) 0.18451(9) 0.05297(2) 0.0159(2) Uani 1 1 d . . . N2 N 0.57696(9) 0.21806(9) 0.02321(2) 0.0162(2) Uani 1 1 d . . . N3 N 0.44297(9) 0.04326(9) 0.02605(3) 0.0193(2) 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 B1 0.0161(7) 0.0161(7) 0.0163(10) 0.000 0.000 0.0080(3) C1 0.0238(7) 0.0215(7) 0.0208(6) -0.0031(5) -0.0040(5) 0.0096(6) C2 0.0171(6) 0.0172(6) 0.0208(6) -0.0028(5) -0.0003(5) 0.0092(5) C3 0.0153(6) 0.0152(6) 0.0217(6) -0.0019(5) 0.0012(5) 0.0077(5) C4 0.0193(6) 0.0148(6) 0.0219(6) 0.0001(5) 0.0042(5) 0.0091(5) C5 0.0213(7) 0.0181(7) 0.0291(7) -0.0001(5) 0.0004(6) 0.0079(6) C6 0.0232(7) 0.0178(7) 0.0399(8) 0.0057(6) 0.0060(6) 0.0061(6) C7 0.0308(8) 0.0234(7) 0.0312(7) 0.0106(6) 0.0106(6) 0.0162(6) C8 0.0288(7) 0.0241(7) 0.0233(6) 0.0020(5) 0.0028(6) 0.0175(6) C9 0.0209(6) 0.0163(6) 0.0238(6) 0.0002(5) 0.0024(5) 0.0097(5) Fe1 0.01299(16) 0.01299(16) 0.0158(2) 0.000 0.000 0.00650(8) N1 0.0165(5) 0.0152(5) 0.0164(5) 0.0012(4) 0.0015(4) 0.0083(4) N2 0.0168(5) 0.0171(5) 0.0153(5) -0.0004(4) 0.0001(4) 0.0090(4) N3 0.0190(6) 0.0174(5) 0.0214(5) -0.0023(4) -0.0003(4) 0.0089(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 N2 1.5464(13) 2_655 ? B1 N2 1.5464(13) . ? B1 N2 1.5464(13) 3_665 ? B1 H1 1.0000 . ? C1 C2 1.4902(18) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N3 1.3296(17) . ? C2 N2 1.3421(17) . ? C3 N1 1.3467(17) . ? C3 N3 1.3522(17) . ? C3 C4 1.4777(18) . ? C4 C9 1.3929(19) . ? C4 C5 1.3995(19) . ? C5 C6 1.386(2) . ? C5 H5 0.9500 . ? C6 C7 1.386(2) . ? C6 H6 0.9500 . ? C7 C8 1.388(2) . ? C7 H7 0.9500 . ? C8 C9 1.3929(19) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? Fe1 N1 2.2334(11) 17_554 ? Fe1 N1 2.2334(11) 16_544 ? Fe1 N1 2.2335(11) . ? Fe1 N1 2.2335(11) 18_654 ? Fe1 N1 2.2336(11) 2_655 ? Fe1 N1 2.2337(11) 3_665 ? N1 N2 1.3825(14) . ? 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 N2 109.46(9) 2_655 . ? N2 B1 N2 109.46(9) 2_655 3_665 ? N2 B1 N2 109.46(9) . 3_665 ? N2 B1 H1 109.5 2_655 . ? N2 B1 H1 109.5 . . ? N2 B1 H1 109.5 3_665 . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N3 C2 N2 111.28(12) . . ? N3 C2 C1 124.71(12) . . ? N2 C2 C1 123.95(12) . . ? N1 C3 N3 113.63(12) . . ? N1 C3 C4 125.56(12) . . ? N3 C3 C4 120.81(12) . . ? C9 C4 C5 119.15(13) . . ? C9 C4 C3 123.28(12) . . ? C5 C4 C3 117.57(12) . . ? C6 C5 C4 120.36(14) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 120.13(14) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C8 120.05(14) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C9 120.03(14) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C4 120.24(13) . . ? C8 C9 H9 119.9 . . ? C4 C9 H9 119.9 . . ? N1 Fe1 N1 88.58(4) 17_554 16_544 ? N1 Fe1 N1 170.86(6) 17_554 . ? N1 Fe1 N1 85.44(5) 16_544 . ? N1 Fe1 N1 88.58(4) 17_554 18_654 ? N1 Fe1 N1 88.58(4) 16_544 18_654 ? N1 Fe1 N1 98.16(5) . 18_654 ? N1 Fe1 N1 98.16(6) 17_554 2_655 ? N1 Fe1 N1 170.86(6) 16_544 2_655 ? N1 Fe1 N1 88.57(4) . 2_655 ? N1 Fe1 N1 85.44(5) 18_654 2_655 ? N1 Fe1 N1 85.45(5) 17_554 3_665 ? N1 Fe1 N1 98.16(5) 16_544 3_665 ? N1 Fe1 N1 88.57(4) . 3_665 ? N1 Fe1 N1 170.86(6) 18_654 3_665 ? N1 Fe1 N1 88.57(4) 2_655 3_665 ? C3 N1 N2 103.14(10) . . ? C3 N1 Fe1 141.91(9) . . ? N2 N1 Fe1 109.57(8) . . ? C2 N2 N1 108.22(10) . . ? C2 N2 B1 130.28(12) . . ? N1 N2 B1 121.25(12) . . ? C2 N3 C3 103.70(11) . . ? 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 C3 C4 C9 -14.7(2) . . . . ? N3 C3 C4 C9 164.46(13) . . . . ? N1 C3 C4 C5 165.21(13) . . . . ? N3 C3 C4 C5 -15.58(19) . . . . ? C9 C4 C5 C6 1.9(2) . . . . ? C3 C4 C5 C6 -178.05(13) . . . . ? C4 C5 C6 C7 -0.3(2) . . . . ? C5 C6 C7 C8 -1.2(2) . . . . ? C6 C7 C8 C9 1.2(2) . . . . ? C7 C8 C9 C4 0.4(2) . . . . ? C5 C4 C9 C8 -2.0(2) . . . . ? C3 C4 C9 C8 177.98(12) . . . . ? N3 C3 N1 N2 -1.41(14) . . . . ? C4 C3 N1 N2 177.85(12) . . . . ? N3 C3 N1 Fe1 147.37(11) . . . . ? C4 C3 N1 Fe1 -33.4(2) . . . . ? N1 Fe1 N1 C3 -18.61(12) 16_544 . . . ? N1 Fe1 N1 C3 69.29(14) 18_654 . . . ? N1 Fe1 N1 C3 154.48(15) 2_655 . . . ? N1 Fe1 N1 C3 -116.92(16) 3_665 . . . ? N1 Fe1 N1 N2 129.00(9) 16_544 . . . ? N1 Fe1 N1 N2 -143.10(9) 18_654 . . . ? N1 Fe1 N1 N2 -57.91(6) 2_655 . . . ? N1 Fe1 N1 N2 30.69(7) 3_665 . . . ? N3 C2 N2 N1 -1.64(15) . . . . ? C1 C2 N2 N1 175.58(12) . . . . ? N3 C2 N2 B1 172.65(10) . . . . ? C1 C2 N2 B1 -10.1(2) . . . . ? C3 N1 N2 C2 1.78(13) . . . . ? Fe1 N1 N2 C2 -158.38(8) . . . . ? C3 N1 N2 B1 -173.12(9) . . . . ? Fe1 N1 N2 B1 26.72(12) . . . . ? N2 B1 N2 C2 -132.36(16) 2_655 . . . ? N2 B1 N2 C2 107.68(19) 3_665 . . . ? N2 B1 N2 N1 41.29(16) 2_655 . . . ? N2 B1 N2 N1 -78.67(12) 3_665 . . . ? N2 C2 N3 C3 0.74(14) . . . . ? C1 C2 N3 C3 -176.46(13) . . . . ? N1 C3 N3 C2 0.47(14) . . . . ? C4 C3 N3 C2 -178.82(12) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.449 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.052 data_08mz356_0m _database_code_depnum_ccdc_archive 'CCDC 850808' #TrackingRef '- combined cifs - new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H50 B2 Mn N18' _chemical_formula_weight 1027.68 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z+1/2' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'y+2/3, x+1/3, -z+5/6' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'y+1/3, x+2/3, -z+7/6' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z-1/2' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-y+2/3, -x+1/3, z-1/6' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-y+1/3, -x+2/3, z+1/6' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' _cell_length_a 13.8711(8) _cell_length_b 13.8711(8) _cell_length_c 43.853(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7307.2(11) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3504 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 31.40 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3210 _exptl_absorpt_coefficient_mu 0.332 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.620 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details 'Apex2 v2008.2-4 (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 14357 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -58 _diffrn_reflns_limit_l_max 58 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2031 _reflns_number_gt 1674 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2008.2-4 (Bruker, 2008)' _computing_cell_refinement 'Apex2 v2008.2-4 ' _computing_data_reduction 'Apex2 v2008.2-4 ' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0476P)^2^+10.5378P] 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 2031 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.6667 0.3333 0.01083(6) 0.0197(5) Uani 1 3 d S . . H1 H 0.6667 0.3333 -0.0120 0.024 Uiso 1 3 calc SR . . C1 C 0.85981(14) 0.31753(14) -0.02393(4) 0.0268(4) Uani 1 1 d . . . H1A H 0.9348 0.3443 -0.0320 0.040 Uiso 1 1 calc R . . H1B H 0.8205 0.3445 -0.0368 0.040 Uiso 1 1 calc R . . H1C H 0.8189 0.2359 -0.0238 0.040 Uiso 1 1 calc R . . C2 C 0.86764(13) 0.35962(12) 0.00761(4) 0.0218(3) Uani 1 1 d . . . C3 C 0.92432(12) 0.42023(12) 0.05203(3) 0.0209(3) Uani 1 1 d . . . C4 C 1.00106(12) 0.46634(12) 0.07823(4) 0.0222(3) Uani 1 1 d . . . C5 C 1.10018(14) 0.46278(14) 0.07704(4) 0.0284(4) Uani 1 1 d . . . H5 H 1.1171 0.4340 0.0595 0.034 Uiso 1 1 calc R . . C6 C 1.17359(14) 0.50092(15) 0.10136(4) 0.0331(4) Uani 1 1 d . . . H6 H 1.2404 0.4979 0.1004 0.040 Uiso 1 1 calc R . . C7 C 1.15009(14) 0.54353(14) 0.12706(4) 0.0316(4) Uani 1 1 d . . . H7 H 1.2000 0.5682 0.1439 0.038 Uiso 1 1 calc R . . C8 C 1.05348(14) 0.55008(13) 0.12823(4) 0.0272(4) Uani 1 1 d . . . H8 H 1.0379 0.5807 0.1457 0.033 Uiso 1 1 calc R . . C9 C 0.97934(13) 0.51162(13) 0.10376(4) 0.0242(3) Uani 1 1 d . . . H9 H 0.9134 0.5164 0.1046 0.029 Uiso 1 1 calc R . . Mn1 Mn 0.6667 0.3333 0.0833 0.01777(15) Uani 1 6 d S . . N1 N 0.78262(10) 0.35925(10) 0.02257(3) 0.0196(3) Uani 1 1 d . . . N2 N 0.81777(10) 0.39691(10) 0.05186(3) 0.0199(3) Uani 1 1 d . . . N3 N 0.95746(11) 0.39802(11) 0.02521(3) 0.0231(3) 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 B1 0.0194(8) 0.0194(8) 0.0205(13) 0.000 0.000 0.0097(4) C1 0.0243(8) 0.0289(8) 0.0271(8) -0.0004(6) 0.0035(6) 0.0133(7) C2 0.0202(7) 0.0179(7) 0.0268(8) 0.0037(6) 0.0035(6) 0.0092(6) C3 0.0178(7) 0.0165(7) 0.0278(8) 0.0030(6) 0.0020(6) 0.0082(6) C4 0.0174(7) 0.0178(7) 0.0290(8) 0.0040(6) -0.0003(6) 0.0071(6) C5 0.0207(8) 0.0263(8) 0.0375(9) 0.0000(7) -0.0006(7) 0.0112(7) C6 0.0205(8) 0.0329(9) 0.0459(10) 0.0005(8) -0.0055(7) 0.0134(7) C7 0.0250(8) 0.0240(8) 0.0388(9) 0.0012(7) -0.0110(7) 0.0070(7) C8 0.0259(8) 0.0202(8) 0.0297(8) 0.0012(6) -0.0028(6) 0.0070(6) C9 0.0185(7) 0.0212(7) 0.0295(8) 0.0043(6) 0.0000(6) 0.0076(6) Mn1 0.01613(19) 0.01613(19) 0.0211(3) 0.000 0.000 0.00806(9) N1 0.0192(6) 0.0175(6) 0.0216(6) 0.0009(5) 0.0013(5) 0.0088(5) N2 0.0179(6) 0.0189(6) 0.0226(6) 0.0003(5) -0.0008(5) 0.0090(5) N3 0.0195(6) 0.0213(6) 0.0279(7) 0.0021(5) 0.0017(5) 0.0097(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 N1 1.5500(16) 2_655 ? B1 N1 1.5501(16) 3_665 ? B1 N1 1.5502(16) . ? B1 H1 1.0000 . ? C1 C2 1.484(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N3 1.329(2) . ? C2 N1 1.3471(19) . ? C3 N2 1.3457(19) . ? C3 N3 1.353(2) . ? C3 C4 1.477(2) . ? C4 C9 1.388(2) . ? C4 C5 1.401(2) . ? C5 C6 1.384(2) . ? C5 H5 0.9500 . ? C6 C7 1.385(3) . ? C6 H6 0.9500 . ? C7 C8 1.389(3) . ? C7 H7 0.9500 . ? C8 C9 1.395(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? Mn1 N2 2.2863(12) 16_544 ? Mn1 N2 2.2863(12) 18_654 ? Mn1 N2 2.2864(12) . ? Mn1 N2 2.2864(12) 2_655 ? Mn1 N2 2.2864(12) 17_554 ? Mn1 N2 2.2865(12) 3_665 ? N1 N2 1.3806(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 B1 N1 109.56(11) 2_655 3_665 ? N1 B1 N1 109.55(11) 2_655 . ? N1 B1 N1 109.55(11) 3_665 . ? N1 B1 H1 109.4 2_655 . ? N1 B1 H1 109.4 3_665 . ? N1 B1 H1 109.4 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N3 C2 N1 111.24(14) . . ? N3 C2 C1 124.61(14) . . ? N1 C2 C1 124.09(14) . . ? N2 C3 N3 113.43(13) . . ? N2 C3 C4 125.14(13) . . ? N3 C3 C4 121.43(13) . . ? C9 C4 C5 118.99(15) . . ? C9 C4 C3 123.41(14) . . ? C5 C4 C3 117.59(14) . . ? C6 C5 C4 120.35(17) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 120.33(16) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C8 119.91(16) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C9 119.85(16) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C4 C9 C8 120.53(15) . . ? C4 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? N2 Mn1 N2 87.33(4) 16_544 18_654 ? N2 Mn1 N2 98.73(6) 16_544 . ? N2 Mn1 N2 171.66(6) 18_654 . ? N2 Mn1 N2 87.25(6) 16_544 2_655 ? N2 Mn1 N2 98.74(6) 18_654 2_655 ? N2 Mn1 N2 87.32(4) . 2_655 ? N2 Mn1 N2 87.33(4) 16_544 17_554 ? N2 Mn1 N2 87.33(4) 18_654 17_554 ? N2 Mn1 N2 87.24(6) . 17_554 ? N2 Mn1 N2 171.66(6) 2_655 17_554 ? N2 Mn1 N2 171.67(6) 16_544 3_665 ? N2 Mn1 N2 87.25(6) 18_654 3_665 ? N2 Mn1 N2 87.32(4) . 3_665 ? N2 Mn1 N2 87.32(4) 2_655 3_665 ? N2 Mn1 N2 98.73(6) 17_554 3_665 ? C2 N1 N2 107.97(12) . . ? C2 N1 B1 130.10(15) . . ? N2 N1 B1 121.72(14) . . ? C3 N2 N1 103.52(12) . . ? C3 N2 Mn1 140.73(10) . . ? N1 N2 Mn1 109.49(9) . . ? C2 N3 C3 103.81(13) . . ? 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 C3 C4 C9 -13.3(2) . . . . ? N3 C3 C4 C9 166.26(14) . . . . ? N2 C3 C4 C5 166.18(15) . . . . ? N3 C3 C4 C5 -14.3(2) . . . . ? C9 C4 C5 C6 1.9(2) . . . . ? C3 C4 C5 C6 -177.63(15) . . . . ? C4 C5 C6 C7 -0.3(3) . . . . ? C5 C6 C7 C8 -1.3(3) . . . . ? C6 C7 C8 C9 1.3(3) . . . . ? C5 C4 C9 C8 -1.8(2) . . . . ? C3 C4 C9 C8 177.63(14) . . . . ? C7 C8 C9 C4 0.3(2) . . . . ? N3 C2 N1 N2 -1.56(17) . . . . ? C1 C2 N1 N2 175.78(14) . . . . ? N3 C2 N1 B1 173.28(11) . . . . ? C1 C2 N1 B1 -9.4(2) . . . . ? N1 B1 N1 C2 -133.72(18) 2_655 . . . ? N1 B1 N1 C2 106.1(2) 3_665 . . . ? N1 B1 N1 N2 40.51(19) 2_655 . . . ? N1 B1 N1 N2 -79.70(14) 3_665 . . . ? N3 C3 N2 N1 -1.11(16) . . . . ? C4 C3 N2 N1 178.45(13) . . . . ? N3 C3 N2 Mn1 145.62(13) . . . . ? C4 C3 N2 Mn1 -34.8(2) . . . . ? C2 N1 N2 C3 1.56(15) . . . . ? B1 N1 N2 C3 -173.80(11) . . . . ? C2 N1 N2 Mn1 -156.82(9) . . . . ? B1 N1 N2 Mn1 27.82(14) . . . . ? N2 Mn1 N2 C3 69.88(15) 16_544 . . . ? N2 Mn1 N2 C3 156.69(17) 2_655 . . . ? N2 Mn1 N2 C3 -16.99(14) 17_554 . . . ? N2 Mn1 N2 C3 -115.87(18) 3_665 . . . ? N2 Mn1 N2 N1 -144.57(10) 16_544 . . . ? N2 Mn1 N2 N1 -57.77(7) 2_655 . . . ? N2 Mn1 N2 N1 128.56(11) 17_554 . . . ? N2 Mn1 N2 N1 29.68(8) 3_665 . . . ? N1 C2 N3 C3 0.84(16) . . . . ? C1 C2 N3 C3 -176.49(15) . . . . ? N2 C3 N3 C2 0.21(17) . . . . ? C4 C3 N3 C2 -179.37(13) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.685 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.055