# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Yu-Bin Dong' _publ_contact_author_email YUBINDONG@SDNU.EDU.CN _publ_section_title ; Birdlike Spiro-Metallacyclic Complexes Based on Bent Oxadiazole Bridging Ligand ; loop_ _publ_author_name 'Yu-Bin Dong' 'Ru-Qi Huang' 'Jian-Ping Ma' 'Dazhong Shen' 'Xia-Xia Zhao' data_1 _database_code_depnum_ccdc_archive 'CCDC 703038' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H32 Cu N18 O2 S2' _chemical_formula_weight 948.52 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 8.414(3) _cell_length_b 11.946(4) _cell_length_c 11.997(4) _cell_angle_alpha 111.512(5) _cell_angle_beta 103.439(5) _cell_angle_gamma 94.999(5) _cell_volume 1071.1(6) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 661 _cell_measurement_theta_min 2.535 _cell_measurement_theta_max 17.972 _exptl_crystal_description plan _exptl_crystal_colour blue _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 487 _exptl_absorpt_coefficient_mu 0.669 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8195 _exptl_absorpt_correction_T_max 0.9867 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5618 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.1130 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3746 _reflns_number_gt 2016 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0902P)^2^+0.0641P] 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 3746 _refine_ls_number_parameters 295 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1487 _refine_ls_R_factor_gt 0.0785 _refine_ls_wR_factor_ref 0.2094 _refine_ls_wR_factor_gt 0.1746 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 Cu1 Cu 0.5000 0.5000 1.0000 0.0576(4) Uani 1 2 d S . . N1 N 0.2183(8) -0.1876(5) 0.3357(5) 0.0659(16) Uani 1 1 d . . . N2 N 0.1000(8) -0.1302(5) 0.2847(5) 0.0669(17) Uani 1 1 d . . . N3 N 0.5882(7) 0.1456(4) 0.9180(4) 0.0475(13) Uani 1 1 d . . . N4 N 0.4435(7) 0.1278(5) 0.9457(5) 0.0610(15) Uani 1 1 d . . . N5 N 0.4996(7) 0.3182(5) 0.9554(4) 0.0517(14) Uani 1 1 d . . . N6 N 0.1436(7) 0.4239(4) 0.6685(4) 0.0511(13) Uani 1 1 d . . . N7 N 0.2726(7) 0.4668(5) 0.6366(5) 0.0566(14) Uani 1 1 d . . . N8 N 0.3567(7) 0.4663(4) 0.8282(4) 0.0511(14) Uani 1 1 d . . . N9 N 0.2501(8) 0.4807(6) 1.0678(5) 0.0727(17) Uani 1 1 d . . . C1 C 0.2924(9) -0.1091(6) 0.4499(6) 0.0555(17) Uani 1 1 d . . . C2 C 0.4185(8) -0.1259(5) 0.5436(6) 0.0515(16) Uani 1 1 d . . . C3 C 0.4752(9) -0.2364(6) 0.5142(7) 0.0630(19) Uani 1 1 d . . . H3 H 0.4359 -0.2972 0.4338 0.076 Uiso 1 1 calc R . . C4 C 0.5903(10) -0.2549(6) 0.6056(8) 0.076(2) Uani 1 1 d . . . H4 H 0.6266 -0.3293 0.5867 0.091 Uiso 1 1 calc R . . C5 C 0.6517(9) -0.1643(6) 0.7246(7) 0.0636(19) Uani 1 1 d . . . H5 H 0.7284 -0.1782 0.7854 0.076 Uiso 1 1 calc R . . C6 C 0.6000(8) -0.0527(6) 0.7541(6) 0.0527(17) Uani 1 1 d . . . C7 C 0.4824(8) -0.0337(6) 0.6634(6) 0.0500(16) Uani 1 1 d . . . H7 H 0.4462 0.0406 0.6827 0.060 Uiso 1 1 calc R . . C8 C 0.6782(8) 0.0473(6) 0.8841(6) 0.0592(18) Uani 1 1 d . . . H8A H 0.6875 0.0105 0.9447 0.071 Uiso 1 1 calc R . . H8B H 0.7900 0.0813 0.8893 0.071 Uiso 1 1 calc R . . C9 C 0.6185(8) 0.2593(6) 0.9241(5) 0.0536(17) Uani 1 1 d . . . H9 H 0.7108 0.2927 0.9086 0.064 Uiso 1 1 calc R . . C10 C 0.3981(8) 0.2324(6) 0.9674(6) 0.0615(19) Uani 1 1 d . . . H10 H 0.3011 0.2476 0.9898 0.074 Uiso 1 1 calc R . . C11 C 0.3961(9) 0.4902(6) 0.7365(6) 0.0587(18) Uani 1 1 d . . . H11 H 0.5046 0.5216 0.7431 0.070 Uiso 1 1 calc R . . C12 C 0.1962(8) 0.4244(5) 0.7820(6) 0.0535(17) Uani 1 1 d . . . H12 H 0.1287 0.3986 0.8227 0.064 Uiso 1 1 calc R . . C13 C -0.0245(8) 0.3847(6) 0.5823(6) 0.0568(17) Uani 1 1 d . . . H13A H -0.0541 0.4507 0.5578 0.068 Uiso 1 1 calc R . . H13B H -0.1027 0.3678 0.6248 0.068 Uiso 1 1 calc R . . C14 C -0.0389(8) 0.2729(6) 0.4681(6) 0.0526(17) Uani 1 1 d . . . C15 C -0.1455(8) 0.2603(6) 0.3542(6) 0.0623(19) Uani 1 1 d . . . H15 H -0.2012 0.3229 0.3488 0.075 Uiso 1 1 calc R . . C16 C -0.1672(9) 0.1533(8) 0.2495(7) 0.076(2) Uani 1 1 d . . . H16 H -0.2407 0.1439 0.1742 0.091 Uiso 1 1 calc R . . C17 C -0.0841(9) 0.0615(7) 0.2537(6) 0.066(2) Uani 1 1 d . . . H17 H -0.1000 -0.0089 0.1818 0.079 Uiso 1 1 calc R . . C18 C 0.0254(8) 0.0735(6) 0.3664(6) 0.0541(17) Uani 1 1 d . . . C19 C 0.0466(8) 0.1810(6) 0.4729(5) 0.0524(17) Uani 1 1 d . . . H19 H 0.1199 0.1903 0.5483 0.063 Uiso 1 1 calc R . . C20 C 0.1118(8) -0.0226(6) 0.3712(5) 0.0533(17) Uani 1 1 d . . . C21 C 0.1596(8) 0.4227(6) 1.1010(6) 0.0504(16) Uani 1 1 d . . . O1 O 0.2329(5) -0.0033(3) 0.4790(3) 0.0497(11) Uani 1 1 d . . . S2 S 0.0557(3) 0.3448(2) 1.1421(2) 0.1015(8) 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 Cu1 0.0904(10) 0.0289(6) 0.0342(7) 0.0039(5) 0.0022(6) -0.0042(6) N1 0.100(5) 0.039(3) 0.047(4) 0.002(3) 0.028(3) 0.000(3) N2 0.100(5) 0.047(4) 0.037(3) 0.002(3) 0.021(3) -0.014(3) N3 0.069(4) 0.038(3) 0.035(3) 0.011(2) 0.020(3) 0.011(3) N4 0.078(4) 0.045(3) 0.066(4) 0.017(3) 0.039(3) 0.009(3) N5 0.066(4) 0.042(3) 0.040(3) 0.010(2) 0.014(3) 0.002(3) N6 0.069(4) 0.037(3) 0.039(3) 0.010(2) 0.011(3) 0.002(3) N7 0.064(4) 0.055(4) 0.047(3) 0.021(3) 0.013(3) 0.000(3) N8 0.066(4) 0.039(3) 0.042(3) 0.013(2) 0.012(3) -0.002(3) N9 0.084(5) 0.064(4) 0.055(4) 0.011(3) 0.013(3) 0.018(3) C1 0.070(5) 0.039(4) 0.052(4) 0.006(3) 0.032(4) -0.004(3) C2 0.059(4) 0.039(4) 0.053(4) 0.007(3) 0.032(4) 0.003(3) C3 0.071(5) 0.043(4) 0.065(5) 0.004(4) 0.032(4) 0.005(4) C4 0.094(6) 0.041(4) 0.101(7) 0.022(5) 0.049(5) 0.022(4) C5 0.066(5) 0.057(5) 0.081(5) 0.031(4) 0.035(4) 0.019(4) C6 0.069(5) 0.039(4) 0.054(4) 0.016(3) 0.030(4) 0.009(3) C7 0.062(4) 0.040(4) 0.051(4) 0.015(3) 0.027(3) 0.008(3) C8 0.072(5) 0.054(4) 0.052(4) 0.021(3) 0.019(4) 0.014(4) C9 0.066(5) 0.047(4) 0.041(4) 0.013(3) 0.015(3) -0.005(3) C10 0.066(5) 0.037(4) 0.082(5) 0.014(4) 0.039(4) 0.003(3) C11 0.067(5) 0.050(4) 0.049(4) 0.015(3) 0.010(4) -0.002(3) C12 0.064(5) 0.042(4) 0.050(4) 0.017(3) 0.014(3) -0.003(3) C13 0.055(4) 0.049(4) 0.058(4) 0.022(3) 0.003(3) 0.002(3) C14 0.057(4) 0.049(4) 0.044(4) 0.017(3) 0.008(3) -0.007(3) C15 0.070(5) 0.060(5) 0.048(4) 0.024(4) 0.002(4) -0.006(4) C16 0.071(5) 0.097(7) 0.045(4) 0.032(5) -0.006(4) -0.008(5) C17 0.071(5) 0.068(5) 0.039(4) 0.010(4) 0.008(4) -0.011(4) C18 0.065(5) 0.046(4) 0.041(4) 0.013(3) 0.009(3) -0.003(3) C19 0.060(4) 0.050(4) 0.035(3) 0.011(3) 0.007(3) -0.006(3) C20 0.067(5) 0.047(4) 0.026(3) -0.001(3) 0.014(3) -0.014(3) C21 0.054(4) 0.041(4) 0.044(4) 0.003(3) 0.011(3) 0.022(3) O1 0.061(3) 0.037(2) 0.036(2) -0.0009(19) 0.016(2) -0.001(2) S2 0.115(2) 0.0934(19) 0.126(2) 0.0586(17) 0.0597(17) 0.0371(15) _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 Cu1 N8 2.004(5) . ? Cu1 N8 2.004(5) 2_667 ? Cu1 N5 2.037(5) 2_667 ? Cu1 N5 2.037(5) . ? Cu1 N9 2.446(7) . ? Cu1 N9 2.446(7) 2_667 ? N1 C1 1.305(8) . ? N1 N2 1.406(7) . ? N2 C20 1.300(8) . ? N3 C9 1.331(7) . ? N3 N4 1.354(7) . ? N3 C8 1.437(7) . ? N4 C10 1.291(8) . ? N5 C9 1.318(8) . ? N5 C10 1.346(7) . ? N6 C12 1.328(7) . ? N6 N7 1.351(7) . ? N6 C13 1.462(7) . ? N7 C11 1.311(7) . ? N8 C12 1.308(7) . ? N8 C11 1.336(7) . ? N9 C21 1.213(8) . ? C1 O1 1.356(7) . ? C1 C2 1.442(9) . ? C2 C3 1.393(8) . ? C2 C7 1.394(8) . ? C3 C4 1.383(9) . ? C3 H3 0.9300 . ? C4 C5 1.380(10) . ? C4 H4 0.9300 . ? C5 C6 1.385(8) . ? C5 H5 0.9300 . ? C6 C7 1.391(8) . ? C6 C8 1.520(8) . ? C7 H7 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.493(9) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C19 1.376(9) . ? C14 C15 1.396(8) . ? C15 C16 1.387(10) . ? C15 H15 0.9300 . ? C16 C17 1.361(10) . ? C16 H16 0.9300 . ? C17 C18 1.398(8) . ? C17 H17 0.9300 . ? C18 C19 1.402(8) . ? C18 C20 1.422(9) . ? C19 H19 0.9300 . ? C20 O1 1.375(7) . ? C21 S2 1.506(8) . ? 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 Cu1 N8 180.000(2) . 2_667 ? N8 Cu1 N5 88.33(19) . 2_667 ? N8 Cu1 N5 91.67(19) 2_667 2_667 ? N8 Cu1 N5 91.67(19) . . ? N8 Cu1 N5 88.33(19) 2_667 . ? N5 Cu1 N5 180.00 2_667 . ? N8 Cu1 N9 89.8(2) . . ? N8 Cu1 N9 90.2(2) 2_667 . ? N5 Cu1 N9 90.2(2) 2_667 . ? N5 Cu1 N9 89.8(2) . . ? N8 Cu1 N9 90.2(2) . 2_667 ? N8 Cu1 N9 89.8(2) 2_667 2_667 ? N5 Cu1 N9 89.8(2) 2_667 2_667 ? N5 Cu1 N9 90.2(2) . 2_667 ? N9 Cu1 N9 180.00 . 2_667 ? C1 N1 N2 105.8(6) . . ? C20 N2 N1 107.0(5) . . ? C9 N3 N4 108.9(5) . . ? C9 N3 C8 130.8(6) . . ? N4 N3 C8 120.2(5) . . ? C10 N4 N3 102.6(5) . . ? C9 N5 C10 101.8(6) . . ? C9 N5 Cu1 126.6(4) . . ? C10 N5 Cu1 130.9(5) . . ? C12 N6 N7 110.1(5) . . ? C12 N6 C13 129.2(5) . . ? N7 N6 C13 120.7(5) . . ? C11 N7 N6 101.2(5) . . ? C12 N8 C11 102.5(5) . . ? C12 N8 Cu1 127.9(4) . . ? C11 N8 Cu1 129.4(4) . . ? C21 N9 Cu1 148.2(5) . . ? N1 C1 O1 112.5(6) . . ? N1 C1 C2 127.8(7) . . ? O1 C1 C2 119.7(6) . . ? C3 C2 C7 119.8(7) . . ? C3 C2 C1 119.4(6) . . ? C7 C2 C1 120.8(6) . . ? C4 C3 C2 119.5(7) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 120.6(7) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.4(7) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C7 119.4(6) . . ? C5 C6 C8 118.7(6) . . ? C7 C6 C8 121.9(6) . . ? C6 C7 C2 120.2(6) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? N3 C8 C6 114.7(5) . . ? N3 C8 H8A 108.6 . . ? C6 C8 H8A 108.6 . . ? N3 C8 H8B 108.6 . . ? C6 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? N5 C9 N3 110.7(6) . . ? N5 C9 H9 124.7 . . ? N3 C9 H9 124.7 . . ? N4 C10 N5 116.0(6) . . ? N4 C10 H10 122.0 . . ? N5 C10 H10 122.0 . . ? N7 C11 N8 116.0(6) . . ? N7 C11 H11 122.0 . . ? N8 C11 H11 122.0 . . ? N8 C12 N6 110.2(6) . . ? N8 C12 H12 124.9 . . ? N6 C12 H12 124.9 . . ? N6 C13 C14 112.1(5) . . ? N6 C13 H13A 109.2 . . ? C14 C13 H13A 109.2 . . ? N6 C13 H13B 109.2 . . ? C14 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C19 C14 C15 119.4(6) . . ? C19 C14 C13 121.7(5) . . ? C15 C14 C13 118.9(6) . . ? C16 C15 C14 119.1(7) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C17 C16 C15 121.9(6) . . ? C17 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? C16 C17 C18 119.8(7) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C19 118.6(7) . . ? C17 C18 C20 120.0(6) . . ? C19 C18 C20 121.5(6) . . ? C14 C19 C18 121.3(6) . . ? C14 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? N2 C20 O1 111.3(6) . . ? N2 C20 C18 129.7(6) . . ? O1 C20 C18 118.9(5) . . ? N9 C21 S2 176.0(6) . . ? C1 O1 C20 103.3(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 C1 N1 N2 C20 0.0(7) . . . . ? C9 N3 N4 C10 -0.4(7) . . . . ? C8 N3 N4 C10 -178.3(5) . . . . ? N8 Cu1 N5 C9 99.7(5) . . . . ? N8 Cu1 N5 C9 -80.3(5) 2_667 . . . ? N5 Cu1 N5 C9 -15(100) 2_667 . . . ? N9 Cu1 N5 C9 -170.6(5) . . . . ? N9 Cu1 N5 C9 9.4(5) 2_667 . . . ? N8 Cu1 N5 C10 -91.7(6) . . . . ? N8 Cu1 N5 C10 88.3(6) 2_667 . . . ? N5 Cu1 N5 C10 154(100) 2_667 . . . ? N9 Cu1 N5 C10 -2.0(6) . . . . ? N9 Cu1 N5 C10 178.0(6) 2_667 . . . ? C12 N6 N7 C11 0.1(6) . . . . ? C13 N6 N7 C11 -179.7(5) . . . . ? N8 Cu1 N8 C12 93(99) 2_667 . . . ? N5 Cu1 N8 C12 -103.0(5) 2_667 . . . ? N5 Cu1 N8 C12 77.0(5) . . . . ? N9 Cu1 N8 C12 -12.8(5) . . . . ? N9 Cu1 N8 C12 167.2(5) 2_667 . . . ? N8 Cu1 N8 C11 -94(99) 2_667 . . . ? N5 Cu1 N8 C11 70.6(5) 2_667 . . . ? N5 Cu1 N8 C11 -109.4(5) . . . . ? N9 Cu1 N8 C11 160.8(5) . . . . ? N9 Cu1 N8 C11 -19.2(5) 2_667 . . . ? N8 Cu1 N9 C21 110.6(10) . . . . ? N8 Cu1 N9 C21 -69.4(10) 2_667 . . . ? N5 Cu1 N9 C21 -161.0(10) 2_667 . . . ? N5 Cu1 N9 C21 19.0(10) . . . . ? N9 Cu1 N9 C21 -13(76) 2_667 . . . ? N2 N1 C1 O1 -0.2(7) . . . . ? N2 N1 C1 C2 176.9(6) . . . . ? N1 C1 C2 C3 1.0(10) . . . . ? O1 C1 C2 C3 177.9(5) . . . . ? N1 C1 C2 C7 -178.1(6) . . . . ? O1 C1 C2 C7 -1.1(9) . . . . ? C7 C2 C3 C4 2.1(9) . . . . ? C1 C2 C3 C4 -176.9(6) . . . . ? C2 C3 C4 C5 -1.3(10) . . . . ? C3 C4 C5 C6 -0.5(10) . . . . ? C4 C5 C6 C7 1.5(9) . . . . ? C4 C5 C6 C8 -176.5(6) . . . . ? C5 C6 C7 C2 -0.6(9) . . . . ? C8 C6 C7 C2 177.3(5) . . . . ? C3 C2 C7 C6 -1.2(9) . . . . ? C1 C2 C7 C6 177.9(5) . . . . ? C9 N3 C8 C6 -104.0(7) . . . . ? N4 N3 C8 C6 73.4(7) . . . . ? C5 C6 C8 N3 -164.0(5) . . . . ? C7 C6 C8 N3 18.1(8) . . . . ? C10 N5 C9 N3 0.1(7) . . . . ? Cu1 N5 C9 N3 171.3(3) . . . . ? N4 N3 C9 N5 0.2(7) . . . . ? C8 N3 C9 N5 177.7(5) . . . . ? N3 N4 C10 N5 0.5(8) . . . . ? C9 N5 C10 N4 -0.4(8) . . . . ? Cu1 N5 C10 N4 -171.1(4) . . . . ? N6 N7 C11 N8 -0.2(7) . . . . ? C12 N8 C11 N7 0.2(7) . . . . ? Cu1 N8 C11 N7 -174.6(4) . . . . ? C11 N8 C12 N6 -0.1(7) . . . . ? Cu1 N8 C12 N6 174.8(4) . . . . ? N7 N6 C12 N8 0.0(7) . . . . ? C13 N6 C12 N8 179.8(5) . . . . ? C12 N6 C13 C14 -113.0(7) . . . . ? N7 N6 C13 C14 66.8(7) . . . . ? N6 C13 C14 C19 36.0(8) . . . . ? N6 C13 C14 C15 -145.8(5) . . . . ? C19 C14 C15 C16 2.3(9) . . . . ? C13 C14 C15 C16 -176.0(6) . . . . ? C14 C15 C16 C17 -1.8(10) . . . . ? C15 C16 C17 C18 0.7(11) . . . . ? C16 C17 C18 C19 -0.1(10) . . . . ? C16 C17 C18 C20 179.6(6) . . . . ? C15 C14 C19 C18 -1.7(9) . . . . ? C13 C14 C19 C18 176.5(6) . . . . ? C17 C18 C19 C14 0.6(9) . . . . ? C20 C18 C19 C14 -179.1(6) . . . . ? N1 N2 C20 O1 0.2(7) . . . . ? N1 N2 C20 C18 177.2(6) . . . . ? C17 C18 C20 N2 -4.3(10) . . . . ? C19 C18 C20 N2 175.4(6) . . . . ? C17 C18 C20 O1 172.5(5) . . . . ? C19 C18 C20 O1 -7.8(9) . . . . ? Cu1 N9 C21 S2 5(10) . . . . ? N1 C1 O1 C20 0.3(6) . . . . ? C2 C1 O1 C20 -177.1(5) . . . . ? N2 C20 O1 C1 -0.3(6) . . . . ? C18 C20 O1 C1 -177.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.628 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.071 data_60915am _database_code_depnum_ccdc_archive 'CCDC 703039' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H40 Cu N18 O12' _chemical_formula_weight 1028.44 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' O O 0.0106 0.0060 '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 8.335(2) _cell_length_b 12.075(3) _cell_length_c 12.621(3) _cell_angle_alpha 69.886(3) _cell_angle_beta 78.080(4) _cell_angle_gamma 70.235(3) _cell_volume 1116.7(5) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1626 _cell_measurement_theta_min 2.611 _cell_measurement_theta_max 24.292 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 531 _exptl_absorpt_coefficient_mu 0.574 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7988 _exptl_absorpt_correction_T_max 0.9396 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5136 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.15 _reflns_number_total 3826 _reflns_number_gt 3293 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+1.0530P] 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 3826 _refine_ls_number_parameters 322 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1218 _refine_ls_wR_factor_gt 0.1156 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 O5 O 0.1431(5) 0.5719(3) 1.0081(4) 0.1131(14) Uani 1 1 d D . . H5A H 0.1867 0.5050 0.9899 0.170 Uiso 1 1 d RD . . H5B H 0.0346 0.5903 1.0251 0.170 Uiso 1 1 d RD . . O2 O 0.4699(4) 0.3851(3) 0.8708(3) 0.0727(9) Uani 1 1 d . . . Cu1 Cu 0.0000 0.0000 1.0000 0.03207(18) Uani 1 2 d S . . O3 O 0.4121(4) 0.2355(3) 0.8493(3) 0.0799(10) Uani 1 1 d . . . N1 N 0.3408(4) -0.0643(3) 0.3378(2) 0.0415(7) Uani 1 1 d . . . N2 N 0.2023(4) 0.0406(3) 0.3047(2) 0.0415(7) Uani 1 1 d . . . N3 N -0.1685(3) 0.2741(2) 0.7112(2) 0.0306(6) Uani 1 1 d . . . N4 N -0.0281(3) 0.3081(2) 0.7091(2) 0.0402(6) Uani 1 1 d . . . N5 N -0.0451(3) 0.1439(2) 0.8586(2) 0.0322(6) Uani 1 1 d . . . N6 N 0.2270(3) -0.0813(2) 0.9281(2) 0.0343(6) Uani 1 1 d . . . N7 N 0.4292(3) -0.2201(2) 0.8675(2) 0.0365(6) Uani 1 1 d . . . N8 N 0.5003(4) -0.1308(3) 0.8551(3) 0.0503(8) Uani 1 1 d . . . N9 N 0.3750(4) 0.3211(3) 0.8901(3) 0.0462(7) Uani 1 1 d . . . C1 C 0.2685(4) -0.1907(3) 0.9113(3) 0.0355(7) Uani 1 1 d . . . H1 H 0.1952 -0.2391 0.9279 0.043 Uiso 1 1 calc R . . C2 C 0.3754(4) -0.0499(3) 0.8929(3) 0.0460(8) Uani 1 1 d . . . H2 H 0.3868 0.0231 0.8956 0.055 Uiso 1 1 calc R . . C3 C 0.5268(5) -0.3276(3) 0.8296(3) 0.0463(8) Uani 1 1 d . . . H3A H 0.4638 -0.3881 0.8565 0.056 Uiso 1 1 calc R . . H3B H 0.6351 -0.3645 0.8624 0.056 Uiso 1 1 calc R . . C4 C 0.5610(4) -0.2950(3) 0.7023(3) 0.0371(7) Uani 1 1 d . . . C5 C 0.7042(4) -0.3677(3) 0.6543(3) 0.0425(8) Uani 1 1 d . . . H5 H 0.7803 -0.4330 0.7008 0.051 Uiso 1 1 calc R . . C6 C 0.7347(4) -0.3440(3) 0.5381(3) 0.0451(9) Uani 1 1 d . . . H6 H 0.8315 -0.3933 0.5069 0.054 Uiso 1 1 calc R . . C7 C 0.6237(4) -0.2485(3) 0.4680(3) 0.0420(8) Uani 1 1 d . . . H7 H 0.6444 -0.2337 0.3898 0.050 Uiso 1 1 calc R . . C8 C 0.4800(4) -0.1736(3) 0.5146(3) 0.0341(7) Uani 1 1 d . . . C9 C 0.4503(4) -0.1973(3) 0.6320(3) 0.0361(7) Uani 1 1 d . . . H9 H 0.3551 -0.1470 0.6633 0.043 Uiso 1 1 calc R . . C10 C 0.3583(4) -0.0759(3) 0.4404(3) 0.0339(7) Uani 1 1 d . . . C11 C 0.1478(4) 0.0847(3) 0.3894(2) 0.0338(7) Uani 1 1 d . . . C12 C 0.0092(4) 0.1951(3) 0.3971(3) 0.0335(7) Uani 1 1 d . . . C13 C -0.0488(5) 0.2841(3) 0.2982(3) 0.0476(9) Uani 1 1 d . . . H13 H -0.0015 0.2726 0.2279 0.057 Uiso 1 1 calc R . . C14 C -0.1770(5) 0.3894(3) 0.3051(3) 0.0563(10) Uani 1 1 d . . . H14 H -0.2160 0.4497 0.2391 0.068 Uiso 1 1 calc R . . C15 C -0.2484(5) 0.4067(3) 0.4089(3) 0.0469(9) Uani 1 1 d . . . H15 H -0.3351 0.4785 0.4121 0.056 Uiso 1 1 calc R . . C16 C -0.1924(4) 0.3180(3) 0.5088(3) 0.0346(7) Uani 1 1 d . . . C17 C -0.0621(4) 0.2128(3) 0.5018(2) 0.0323(7) Uani 1 1 d . . . H17 H -0.0217 0.1532 0.5678 0.039 Uiso 1 1 calc R . . C18 C -0.2814(4) 0.3374(3) 0.6206(3) 0.0349(7) Uani 1 1 d . . . H18A H -0.3208 0.4249 0.6126 0.042 Uiso 1 1 calc R . . H18B H -0.3810 0.3072 0.6411 0.042 Uiso 1 1 calc R . . C19 C -0.1778(4) 0.1779(3) 0.8002(2) 0.0314(7) Uani 1 1 d . . . H19 H -0.2642 0.1398 0.8189 0.038 Uiso 1 1 calc R . . C20 C 0.0408(4) 0.2280(3) 0.7991(3) 0.0403(8) Uani 1 1 d . . . H20 H 0.1407 0.2281 0.8210 0.048 Uiso 1 1 calc R . . O1 O 0.2407(3) 0.01486(19) 0.47972(17) 0.0348(5) Uani 1 1 d . . . O4 O 0.2372(4) 0.3408(3) 0.9529(3) 0.0681(8) Uani 1 1 d . . . O6 O 0.1404(3) 0.1117(2) 1.06714(19) 0.0482(6) Uani 1 1 d D . . H6A H 0.1835 0.1682 1.0264 0.072 Uiso 1 1 d RD . . H6B H 0.1581 0.0866 1.1364 0.072 Uiso 1 1 d RD . . 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 O5 0.083(2) 0.075(2) 0.183(4) -0.050(3) 0.000(3) -0.021(2) O2 0.0652(19) 0.0565(17) 0.103(2) -0.0180(16) -0.0101(17) -0.0304(15) Cu1 0.0292(3) 0.0385(3) 0.0221(3) -0.0075(2) -0.0007(2) -0.0046(2) O3 0.0557(18) 0.078(2) 0.129(3) -0.065(2) -0.0042(18) -0.0174(16) N1 0.0502(17) 0.0450(16) 0.0313(15) -0.0142(12) -0.0009(12) -0.0152(14) N2 0.0498(17) 0.0475(16) 0.0284(15) -0.0117(12) -0.0021(12) -0.0163(14) N3 0.0282(13) 0.0311(13) 0.0300(14) -0.0092(11) -0.0050(10) -0.0041(11) N4 0.0399(15) 0.0443(16) 0.0381(15) -0.0065(12) -0.0069(12) -0.0185(13) N5 0.0292(13) 0.0408(15) 0.0260(13) -0.0105(11) -0.0010(11) -0.0098(12) N6 0.0332(14) 0.0406(15) 0.0280(14) -0.0127(11) 0.0014(11) -0.0092(12) N7 0.0349(14) 0.0376(15) 0.0335(15) -0.0116(12) -0.0032(11) -0.0054(12) N8 0.0337(16) 0.0507(18) 0.067(2) -0.0238(16) 0.0042(14) -0.0119(14) N9 0.0374(16) 0.0419(17) 0.0550(19) -0.0098(14) -0.0137(14) -0.0055(14) C1 0.0346(17) 0.0392(18) 0.0322(17) -0.0101(14) -0.0020(13) -0.0115(14) C2 0.0356(18) 0.048(2) 0.058(2) -0.0231(17) 0.0024(16) -0.0138(16) C3 0.048(2) 0.0381(19) 0.042(2) -0.0136(15) -0.0072(16) 0.0042(16) C4 0.0342(17) 0.0342(17) 0.0418(19) -0.0162(14) -0.0020(14) -0.0048(14) C5 0.0338(17) 0.0380(18) 0.058(2) -0.0227(16) -0.0065(16) -0.0034(15) C6 0.0318(17) 0.046(2) 0.062(2) -0.0338(18) 0.0089(16) -0.0064(15) C7 0.0404(19) 0.048(2) 0.042(2) -0.0231(16) 0.0087(15) -0.0170(16) C8 0.0342(16) 0.0355(17) 0.0371(18) -0.0166(14) 0.0019(13) -0.0131(14) C9 0.0301(16) 0.0361(17) 0.0405(19) -0.0187(14) 0.0027(13) -0.0041(14) C10 0.0365(17) 0.0388(17) 0.0318(17) -0.0157(14) 0.0056(13) -0.0178(14) C11 0.0405(17) 0.0375(17) 0.0264(16) -0.0051(13) -0.0060(13) -0.0181(14) C12 0.0383(17) 0.0351(17) 0.0317(17) -0.0083(13) -0.0094(13) -0.0148(14) C13 0.062(2) 0.050(2) 0.0290(18) -0.0067(15) -0.0113(16) -0.0143(18) C14 0.071(3) 0.050(2) 0.034(2) 0.0045(16) -0.0221(18) -0.008(2) C15 0.054(2) 0.0342(18) 0.044(2) -0.0028(15) -0.0211(17) -0.0017(16) C16 0.0371(17) 0.0313(16) 0.0370(17) -0.0062(13) -0.0112(14) -0.0114(14) C17 0.0357(17) 0.0303(16) 0.0297(17) -0.0021(12) -0.0112(13) -0.0104(13) C18 0.0340(16) 0.0278(16) 0.0373(18) -0.0065(13) -0.0110(13) -0.0011(13) C19 0.0286(15) 0.0349(16) 0.0289(16) -0.0104(13) -0.0006(12) -0.0073(13) C20 0.0362(17) 0.054(2) 0.0354(18) -0.0117(15) -0.0066(14) -0.0181(16) O1 0.0388(12) 0.0381(12) 0.0292(11) -0.0137(9) -0.0028(9) -0.0100(10) O4 0.0519(17) 0.0690(19) 0.0715(19) -0.0225(15) 0.0042(14) -0.0073(14) O6 0.0627(16) 0.0607(15) 0.0312(12) -0.0097(11) -0.0089(11) -0.0321(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O5 H5A 0.8558 . ? O5 H5B 0.8543 . ? O2 N9 1.219(4) . ? Cu1 N6 2.004(2) . ? Cu1 N6 2.004(2) 2_557 ? Cu1 N5 2.012(2) . ? Cu1 N5 2.012(2) 2_557 ? Cu1 O6 2.484(2) . ? O3 N9 1.229(4) . ? N1 C10 1.287(4) . ? N1 N2 1.400(4) . ? N2 C11 1.289(4) . ? N3 C19 1.321(4) . ? N3 N4 1.358(3) . ? N3 C18 1.460(4) . ? N4 C20 1.302(4) . ? N5 C19 1.326(4) . ? N5 C20 1.361(4) . ? N6 C1 1.327(4) . ? N6 C2 1.359(4) . ? N7 C1 1.316(4) . ? N7 N8 1.347(4) . ? N7 C3 1.459(4) . ? N8 C2 1.302(4) . ? N9 O4 1.254(4) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.506(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C9 1.382(4) . ? C4 C5 1.386(4) . ? C5 C6 1.380(5) . ? C5 H5 0.9300 . ? C6 C7 1.372(5) . ? C6 H6 0.9300 . ? C7 C8 1.393(4) . ? C7 H7 0.9300 . ? C8 C9 1.393(4) . ? C8 C10 1.456(4) . ? C9 H9 0.9300 . ? C10 O1 1.362(4) . ? C11 O1 1.368(4) . ? C11 C12 1.457(4) . ? C12 C13 1.386(4) . ? C12 C17 1.389(4) . ? C13 C14 1.374(5) . ? C13 H13 0.9300 . ? C14 C15 1.376(5) . ? C14 H14 0.9300 . ? C15 C16 1.389(4) . ? C15 H15 0.9300 . ? C16 C17 1.380(4) . ? C16 C18 1.509(5) . ? C17 H17 0.9300 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? O6 H6A 0.8412 . ? O6 H6B 0.8475 . ? 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 H5A O5 H5B 114.3 . . ? N6 Cu1 N6 180.00 . 2_557 ? N6 Cu1 N5 91.83(10) . . ? N6 Cu1 N5 88.17(10) 2_557 . ? N6 Cu1 N5 88.17(10) . 2_557 ? N6 Cu1 N5 91.83(10) 2_557 2_557 ? N5 Cu1 N5 180.00 . 2_557 ? N6 Cu1 O6 90.00(9) . . ? N6 Cu1 O6 90.00(9) 2_557 . ? N5 Cu1 O6 88.98(9) . . ? N5 Cu1 O6 91.02(9) 2_557 . ? C10 N1 N2 106.3(3) . . ? C11 N2 N1 106.9(3) . . ? C19 N3 N4 110.5(2) . . ? C19 N3 C18 128.4(3) . . ? N4 N3 C18 121.1(2) . . ? C20 N4 N3 102.5(2) . . ? C19 N5 C20 102.9(3) . . ? C19 N5 Cu1 124.6(2) . . ? C20 N5 Cu1 132.5(2) . . ? C1 N6 C2 102.8(3) . . ? C1 N6 Cu1 124.9(2) . . ? C2 N6 Cu1 132.2(2) . . ? C1 N7 N8 110.4(3) . . ? C1 N7 C3 129.1(3) . . ? N8 N7 C3 120.5(3) . . ? C2 N8 N7 103.0(3) . . ? O2 N9 O3 121.1(3) . . ? O2 N9 O4 120.5(3) . . ? O3 N9 O4 118.4(3) . . ? N7 C1 N6 109.7(3) . . ? N7 C1 H1 125.2 . . ? N6 C1 H1 125.2 . . ? N8 C2 N6 114.1(3) . . ? N8 C2 H2 122.9 . . ? N6 C2 H2 122.9 . . ? N7 C3 C4 112.1(3) . . ? N7 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N7 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C9 C4 C5 119.1(3) . . ? C9 C4 C3 121.9(3) . . ? C5 C4 C3 119.0(3) . . ? C6 C5 C4 120.4(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 120.7(3) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 119.6(3) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C7 C8 C9 119.5(3) . . ? C7 C8 C10 119.5(3) . . ? C9 C8 C10 120.9(3) . . ? C4 C9 C8 120.6(3) . . ? C4 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? N1 C10 O1 112.2(3) . . ? N1 C10 C8 127.8(3) . . ? O1 C10 C8 119.9(3) . . ? N2 C11 O1 111.6(3) . . ? N2 C11 C12 128.5(3) . . ? O1 C11 C12 119.9(3) . . ? C13 C12 C17 120.1(3) . . ? C13 C12 C11 119.2(3) . . ? C17 C12 C11 120.7(3) . . ? C14 C13 C12 119.2(3) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 120.6(3) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C16 120.8(3) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 118.6(3) . . ? C17 C16 C18 122.4(3) . . ? C15 C16 C18 118.9(3) . . ? C16 C17 C12 120.6(3) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? N3 C18 C16 111.9(2) . . ? N3 C18 H18A 109.2 . . ? C16 C18 H18A 109.2 . . ? N3 C18 H18B 109.2 . . ? C16 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? N3 C19 N5 109.6(3) . . ? N3 C19 H19 125.2 . . ? N5 C19 H19 125.2 . . ? N4 C20 N5 114.5(3) . . ? N4 C20 H20 122.7 . . ? N5 C20 H20 122.7 . . ? C10 O1 C11 103.0(2) . . ? N9 O4 H5A 110.7 . . ? N9 O4 H6A 106.1 . . ? H5A O4 H6A 139.0 . . ? Cu1 O6 H6A 126.4 . . ? Cu1 O6 H6B 118.5 . . ? H6A O6 H6B 114.7 . . ? 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 C10 N1 N2 C11 0.5(3) . . . . ? C19 N3 N4 C20 0.2(3) . . . . ? C18 N3 N4 C20 -177.2(3) . . . . ? N6 Cu1 N5 C19 120.5(2) . . . . ? N6 Cu1 N5 C19 -59.5(2) 2_557 . . . ? N5 Cu1 N5 C19 -13(100) 2_557 . . . ? O6 Cu1 N5 C19 -149.6(2) . . . . ? N6 Cu1 N5 C20 -59.6(3) . . . . ? N6 Cu1 N5 C20 120.4(3) 2_557 . . . ? N5 Cu1 N5 C20 167(100) 2_557 . . . ? O6 Cu1 N5 C20 30.4(3) . . . . ? N6 Cu1 N6 C1 110(100) 2_557 . . . ? N5 Cu1 N6 C1 -118.8(3) . . . . ? N5 Cu1 N6 C1 61.2(3) 2_557 . . . ? O6 Cu1 N6 C1 152.3(3) . . . . ? N6 Cu1 N6 C2 -64(100) 2_557 . . . ? N5 Cu1 N6 C2 66.6(3) . . . . ? N5 Cu1 N6 C2 -113.4(3) 2_557 . . . ? O6 Cu1 N6 C2 -22.4(3) . . . . ? C1 N7 N8 C2 0.0(4) . . . . ? C3 N7 N8 C2 177.3(3) . . . . ? N8 N7 C1 N6 0.7(4) . . . . ? C3 N7 C1 N6 -176.3(3) . . . . ? C2 N6 C1 N7 -1.0(3) . . . . ? Cu1 N6 C1 N7 -176.94(19) . . . . ? N7 N8 C2 N6 -0.6(4) . . . . ? C1 N6 C2 N8 1.0(4) . . . . ? Cu1 N6 C2 N8 176.5(2) . . . . ? C1 N7 C3 C4 108.3(4) . . . . ? N8 N7 C3 C4 -68.5(4) . . . . ? N7 C3 C4 C9 -29.3(5) . . . . ? N7 C3 C4 C5 153.1(3) . . . . ? C9 C4 C5 C6 -0.8(5) . . . . ? C3 C4 C5 C6 176.8(3) . . . . ? C4 C5 C6 C7 -0.2(5) . . . . ? C5 C6 C7 C8 0.9(5) . . . . ? C6 C7 C8 C9 -0.4(5) . . . . ? C6 C7 C8 C10 -177.2(3) . . . . ? C5 C4 C9 C8 1.3(5) . . . . ? C3 C4 C9 C8 -176.3(3) . . . . ? C7 C8 C9 C4 -0.7(5) . . . . ? C10 C8 C9 C4 176.0(3) . . . . ? N2 N1 C10 O1 -0.2(3) . . . . ? N2 N1 C10 C8 177.3(3) . . . . ? C7 C8 C10 N1 17.9(5) . . . . ? C9 C8 C10 N1 -158.9(3) . . . . ? C7 C8 C10 O1 -164.8(3) . . . . ? C9 C8 C10 O1 18.4(4) . . . . ? N1 N2 C11 O1 -0.6(3) . . . . ? N1 N2 C11 C12 178.2(3) . . . . ? N2 C11 C12 C13 -18.1(5) . . . . ? O1 C11 C12 C13 160.5(3) . . . . ? N2 C11 C12 C17 163.3(3) . . . . ? O1 C11 C12 C17 -18.1(4) . . . . ? C17 C12 C13 C14 0.0(5) . . . . ? C11 C12 C13 C14 -178.6(3) . . . . ? C12 C13 C14 C15 -0.4(6) . . . . ? C13 C14 C15 C16 0.0(6) . . . . ? C14 C15 C16 C17 0.8(5) . . . . ? C14 C15 C16 C18 -176.4(3) . . . . ? C15 C16 C17 C12 -1.2(4) . . . . ? C18 C16 C17 C12 176.0(3) . . . . ? C13 C12 C17 C16 0.8(4) . . . . ? C11 C12 C17 C16 179.4(3) . . . . ? C19 N3 C18 C16 -111.3(3) . . . . ? N4 N3 C18 C16 65.6(3) . . . . ? C17 C16 C18 N3 29.4(4) . . . . ? C15 C16 C18 N3 -153.4(3) . . . . ? N4 N3 C19 N5 -0.9(3) . . . . ? C18 N3 C19 N5 176.3(3) . . . . ? C20 N5 C19 N3 1.1(3) . . . . ? Cu1 N5 C19 N3 -178.94(18) . . . . ? N3 N4 C20 N5 0.5(4) . . . . ? C19 N5 C20 N4 -1.0(4) . . . . ? Cu1 N5 C20 N4 179.0(2) . . . . ? N1 C10 O1 C11 -0.1(3) . . . . ? C8 C10 O1 C11 -177.8(3) . . . . ? N2 C11 O1 C10 0.4(3) . . . . ? C12 C11 O1 C10 -178.4(3) . . . . ? O2 N9 O4 H5A 9.3 . . . . ? O3 N9 O4 H5A -171.2 . . . . ? O2 N9 O4 H6A -152.3 . . . . ? O3 N9 O4 H6A 27.2 . . . . ? 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 O6 H6B N2 0.85 2.08 2.926(4) 174.9 1_556 O6 H6A O4 0.84 2.13 2.944(4) 163.2 . O5 H5A O4 0.86 2.08 2.919(5) 167.4 . O5 H5B O4 0.85 2.13 2.976(5) 171.7 2_567 _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 25.15 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.529 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.061 data_3 _database_code_depnum_ccdc_archive 'CCDC 703040' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H36 Cl2 Cu N16 O4' _chemical_formula_weight 939.29 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' 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' 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 8.816(4) _cell_length_b 11.435(5) _cell_length_c 11.563(5) _cell_angle_alpha 106.243(7) _cell_angle_beta 101.104(7) _cell_angle_gamma 106.755(7) _cell_volume 1023.2(8) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 620 _cell_measurement_theta_min 2.463 _cell_measurement_theta_max 19.568 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 483 _exptl_absorpt_coefficient_mu 0.729 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8330 _exptl_absorpt_correction_T_max 0.9241 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5407 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3734 _reflns_number_gt 2679 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3734 _refine_ls_number_parameters 286 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0760 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1261 _refine_ls_wR_factor_gt 0.1164 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _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 Cu1 Cu 0.5000 1.0000 0.5000 0.0439(2) Uani 1 2 d S . . N1 N 0.1302(4) 0.3363(3) -0.1961(3) 0.0391(7) Uani 1 1 d . . . N2 N 0.2563(4) 0.4111(3) -0.2324(3) 0.0413(8) Uani 1 1 d . . . N3 N 0.2178(4) 0.6078(2) 0.3925(2) 0.0317(7) Uani 1 1 d . . . N4 N 0.3963(4) 0.8024(3) 0.4428(3) 0.0352(7) Uani 1 1 d . . . N5 N 0.5776(4) 0.9893(3) 0.3473(3) 0.0356(7) Uani 1 1 d . . . N6 N 0.7076(4) 0.9679(2) 0.2064(2) 0.0319(7) Uani 1 1 d . . . N7 N 0.5921(4) 1.0166(3) 0.1658(3) 0.0417(8) Uani 1 1 d . . . N8 N 0.3666(4) 0.5965(3) 0.4222(3) 0.0488(8) Uani 1 1 d . . . C1 C 0.5198(5) 1.0277(3) 0.2546(3) 0.0409(9) Uani 1 1 d . . . H1 H 0.4343 1.0599 0.2533 0.049 Uiso 1 1 calc R . . C2 C 0.6974(5) 0.9533(3) 0.3144(3) 0.0385(9) Uani 1 1 d . . . H2 H 0.7646 0.9223 0.3604 0.046 Uiso 1 1 calc R . . C3 C 0.8125(4) 0.9340(3) 0.1297(3) 0.0380(9) Uani 1 1 d . . . H3A H 0.8896 0.9042 0.1742 0.046 Uiso 1 1 calc R . . H3B H 0.8765 1.0112 0.1166 0.046 Uiso 1 1 calc R . . C4 C 0.7114(4) 0.8288(3) 0.0041(3) 0.0305(8) Uani 1 1 d . . . C5 C 0.7558(4) 0.8340(3) -0.1038(3) 0.0383(9) Uani 1 1 d . . . H5 H 0.8443 0.9054 -0.0983 0.046 Uiso 1 1 calc R . . C6 C 0.6707(5) 0.7351(3) -0.2185(3) 0.0410(9) Uani 1 1 d . . . H6 H 0.7049 0.7392 -0.2890 0.049 Uiso 1 1 calc R . . C7 C 0.5359(5) 0.6304(3) -0.2307(3) 0.0397(9) Uani 1 1 d . . . H7 H 0.4777 0.5645 -0.3088 0.048 Uiso 1 1 calc R . . C8 C 0.4881(4) 0.6247(3) -0.1234(3) 0.0304(8) Uani 1 1 d . . . C9 C 0.5756(4) 0.7234(3) -0.0075(3) 0.0302(8) Uani 1 1 d . . . H9 H 0.5428 0.7189 0.0634 0.036 Uiso 1 1 calc R . . C10 C 0.3446(4) 0.5139(3) -0.1352(3) 0.0317(8) Uani 1 1 d . . . C11 C 0.1535(4) 0.4007(3) -0.0787(3) 0.0306(8) Uani 1 1 d . . . C12 C 0.0580(4) 0.3673(3) 0.0041(3) 0.0281(7) Uani 1 1 d . . . C13 C -0.0844(4) 0.2549(3) -0.0451(3) 0.0364(8) Uani 1 1 d . . . H13 H -0.1191 0.2033 -0.1302 0.044 Uiso 1 1 calc R . . C14 C -0.1736(4) 0.2212(3) 0.0344(3) 0.0388(9) Uani 1 1 d . . . H14 H -0.2682 0.1458 0.0027 0.047 Uiso 1 1 calc R . . C15 C -0.1233(4) 0.2985(3) 0.1602(3) 0.0350(8) Uani 1 1 d . . . H15 H -0.1846 0.2749 0.2126 0.042 Uiso 1 1 calc R . . C16 C 0.0185(4) 0.4119(3) 0.2099(3) 0.0302(8) Uani 1 1 d . . . C17 C 0.1075(4) 0.4453(3) 0.1306(3) 0.0292(8) Uani 1 1 d . . . H17 H 0.2019 0.5209 0.1624 0.035 Uiso 1 1 calc R . . C18 C 0.0659(4) 0.4929(3) 0.3482(3) 0.0368(9) Uani 1 1 d . . . H18A H -0.0244 0.5211 0.3639 0.044 Uiso 1 1 calc R . . H18B H 0.0794 0.4382 0.3972 0.044 Uiso 1 1 calc R . . C19 C 0.4695(5) 0.7161(4) 0.4520(4) 0.0491(10) Uani 1 1 d . . . H19 H 0.5842 0.7393 0.4774 0.059 Uiso 1 1 calc R . . C20 C 0.2359(5) 0.7305(3) 0.4038(3) 0.0357(8) Uani 1 1 d . . . H20 H 0.1500 0.7609 0.3870 0.043 Uiso 1 1 calc R . . Cl1 Cl 0.80774(12) 0.98817(8) 0.62335(8) 0.0438(3) Uani 1 1 d . . . O1 O 0.2880(3) 0.51454(19) -0.03366(19) 0.0299(5) Uani 1 1 d . . . O2 O 0.0908(5) 0.2668(3) 0.4796(3) 0.0889(11) Uani 1 1 d D . . H2A H 0.0656 0.1851 0.4401 0.050 Uiso 1 1 d RD . . H2B H 0.1619 0.3005 0.5511 0.050 Uiso 1 1 d RD . . 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 Cu1 0.0592(5) 0.0267(3) 0.0322(4) -0.0001(3) 0.0207(3) 0.0019(3) N1 0.0386(19) 0.0329(16) 0.0338(17) 0.0049(13) 0.0051(14) 0.0066(14) N2 0.045(2) 0.0367(17) 0.0321(17) 0.0058(14) 0.0094(15) 0.0085(15) N3 0.0358(18) 0.0261(15) 0.0271(15) 0.0051(12) 0.0071(13) 0.0084(13) N4 0.0364(19) 0.0282(15) 0.0321(16) 0.0034(13) 0.0097(14) 0.0066(14) N5 0.0404(19) 0.0316(16) 0.0320(17) 0.0064(13) 0.0131(14) 0.0122(14) N6 0.0335(17) 0.0284(15) 0.0292(16) 0.0069(12) 0.0096(13) 0.0078(13) N7 0.044(2) 0.0480(19) 0.0433(19) 0.0217(15) 0.0143(16) 0.0245(16) N8 0.040(2) 0.0356(18) 0.055(2) 0.0040(15) -0.0015(16) 0.0135(16) C1 0.040(2) 0.044(2) 0.040(2) 0.0110(18) 0.0112(18) 0.0216(18) C2 0.046(2) 0.037(2) 0.033(2) 0.0135(16) 0.0112(18) 0.0170(18) C3 0.033(2) 0.038(2) 0.046(2) 0.0159(17) 0.0175(18) 0.0121(17) C4 0.029(2) 0.0305(18) 0.037(2) 0.0140(15) 0.0123(16) 0.0136(15) C5 0.034(2) 0.041(2) 0.049(2) 0.0217(18) 0.0208(18) 0.0154(17) C6 0.050(3) 0.051(2) 0.037(2) 0.0227(19) 0.0260(19) 0.025(2) C7 0.045(2) 0.045(2) 0.034(2) 0.0117(17) 0.0135(18) 0.0240(19) C8 0.031(2) 0.0302(18) 0.0352(19) 0.0128(15) 0.0118(16) 0.0161(15) C9 0.030(2) 0.0341(18) 0.0312(19) 0.0146(15) 0.0130(15) 0.0134(16) C10 0.034(2) 0.0317(18) 0.0302(19) 0.0092(15) 0.0101(16) 0.0149(16) C11 0.030(2) 0.0219(17) 0.035(2) 0.0085(15) 0.0015(15) 0.0085(15) C12 0.030(2) 0.0230(16) 0.0333(19) 0.0128(14) 0.0072(15) 0.0119(15) C13 0.034(2) 0.0277(18) 0.038(2) 0.0061(16) -0.0003(17) 0.0103(16) C14 0.034(2) 0.0245(18) 0.047(2) 0.0085(16) 0.0073(18) 0.0030(16) C15 0.033(2) 0.0265(17) 0.045(2) 0.0150(16) 0.0126(17) 0.0062(16) C16 0.0285(19) 0.0246(17) 0.037(2) 0.0127(15) 0.0067(16) 0.0089(15) C17 0.030(2) 0.0212(16) 0.0327(19) 0.0089(14) 0.0057(15) 0.0073(14) C18 0.035(2) 0.0344(19) 0.035(2) 0.0122(16) 0.0101(17) 0.0046(16) C19 0.032(2) 0.041(2) 0.051(3) -0.0010(19) -0.0007(19) 0.0066(19) C20 0.038(2) 0.0293(19) 0.036(2) 0.0079(16) 0.0103(17) 0.0112(17) Cl1 0.0431(6) 0.0393(5) 0.0377(5) 0.0068(4) 0.0034(4) 0.0111(4) O1 0.0295(13) 0.0259(11) 0.0279(12) 0.0060(10) 0.0065(10) 0.0056(10) O2 0.122(3) 0.093(2) 0.069(2) 0.0262(19) 0.026(2) 0.068(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N5 1.998(3) . ? Cu1 N5 1.998(3) 2_676 ? Cu1 N4 2.030(3) . ? Cu1 N4 2.030(3) 2_676 ? Cu1 Cl1 2.8710(15) . ? N1 C11 1.294(4) . ? N1 N2 1.405(4) . ? N2 C10 1.284(4) . ? N3 C20 1.331(4) . ? N3 N8 1.344(4) . ? N3 C18 1.458(4) . ? N4 C20 1.325(4) . ? N4 C19 1.342(4) . ? N5 C2 1.322(4) . ? N5 C1 1.336(4) . ? N6 C2 1.321(4) . ? N6 N7 1.362(4) . ? N6 C3 1.457(4) . ? N7 C1 1.304(4) . ? N8 C19 1.308(5) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.502(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C9 1.385(4) . ? C4 C5 1.389(4) . ? C5 C6 1.375(5) . ? C5 H5 0.9300 . ? C6 C7 1.374(5) . ? C6 H6 0.9300 . ? C7 C8 1.397(4) . ? C7 H7 0.9300 . ? C8 C9 1.385(4) . ? C8 C10 1.461(5) . ? C9 H9 0.9300 . ? C10 O1 1.360(4) . ? C11 O1 1.366(4) . ? C11 C12 1.449(5) . ? C12 C17 1.388(4) . ? C12 C13 1.392(4) . ? C13 C14 1.384(5) . ? C13 H13 0.9300 . ? C14 C15 1.379(5) . ? C14 H14 0.9300 . ? C15 C16 1.395(4) . ? C15 H15 0.9300 . ? C16 C17 1.379(4) . ? C16 C18 1.511(4) . ? C17 H17 0.9300 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? O2 H2A 0.8562 . ? O2 H2B 0.8415 . ? 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 Cu1 N5 180.00 . 2_676 ? N5 Cu1 N4 91.83(11) . . ? N5 Cu1 N4 88.17(11) 2_676 . ? N5 Cu1 N4 88.17(11) . 2_676 ? N5 Cu1 N4 91.83(11) 2_676 2_676 ? N4 Cu1 N4 180.00 . 2_676 ? N5 Cu1 Cl1 88.06(10) . . ? N5 Cu1 Cl1 91.94(10) 2_676 . ? N4 Cu1 Cl1 89.13(9) . . ? N4 Cu1 Cl1 90.87(9) 2_676 . ? C11 N1 N2 106.3(3) . . ? C10 N2 N1 106.8(3) . . ? C20 N3 N8 110.5(3) . . ? C20 N3 C18 129.1(3) . . ? N8 N3 C18 120.3(3) . . ? C20 N4 C19 103.5(3) . . ? C20 N4 Cu1 126.8(2) . . ? C19 N4 Cu1 129.1(3) . . ? C2 N5 C1 103.1(3) . . ? C2 N5 Cu1 131.7(3) . . ? C1 N5 Cu1 125.1(2) . . ? C2 N6 N7 109.6(3) . . ? C2 N6 C3 129.9(3) . . ? N7 N6 C3 120.5(3) . . ? C1 N7 N6 102.2(3) . . ? C19 N8 N3 102.6(3) . . ? N7 C1 N5 115.1(3) . . ? N7 C1 H1 122.4 . . ? N5 C1 H1 122.4 . . ? N6 C2 N5 109.9(3) . . ? N6 C2 H2 125.0 . . ? N5 C2 H2 125.0 . . ? N6 C3 C4 111.5(3) . . ? N6 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? N6 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C9 C4 C5 118.2(3) . . ? C9 C4 C3 121.7(3) . . ? C5 C4 C3 120.0(3) . . ? C6 C5 C4 121.0(3) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C7 C6 C5 121.0(3) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 118.7(3) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? C9 C8 C7 120.1(3) . . ? C9 C8 C10 120.6(3) . . ? C7 C8 C10 119.2(3) . . ? C8 C9 C4 120.9(3) . . ? C8 C9 H9 119.6 . . ? C4 C9 H9 119.6 . . ? N2 C10 O1 111.9(3) . . ? N2 C10 C8 128.9(3) . . ? O1 C10 C8 119.2(3) . . ? N1 C11 O1 111.5(3) . . ? N1 C11 C12 128.9(3) . . ? O1 C11 C12 119.6(3) . . ? C17 C12 C13 120.2(3) . . ? C17 C12 C11 120.8(3) . . ? C13 C12 C11 118.9(3) . . ? C14 C13 C12 119.0(3) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C15 C14 C13 120.5(3) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 120.7(3) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 118.7(3) . . ? C17 C16 C18 123.2(3) . . ? C15 C16 C18 118.1(3) . . ? C16 C17 C12 120.8(3) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? N3 C18 C16 114.3(3) . . ? N3 C18 H18A 108.7 . . ? C16 C18 H18A 108.7 . . ? N3 C18 H18B 108.7 . . ? C16 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? N8 C19 N4 114.6(4) . . ? N8 C19 H19 122.7 . . ? N4 C19 H19 122.7 . . ? N4 C20 N3 108.9(3) . . ? N4 C20 H20 125.6 . . ? N3 C20 H20 125.6 . . ? C10 O1 C11 103.5(2) . . ? H2A O2 H2B 117.1 . . ? 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 C11 N1 N2 C10 -0.2(4) . . . . ? N5 Cu1 N4 C20 -110.7(3) . . . . ? N5 Cu1 N4 C20 69.3(3) 2_676 . . . ? N4 Cu1 N4 C20 46(100) 2_676 . . . ? Cl1 Cu1 N4 C20 161.2(3) . . . . ? N5 Cu1 N4 C19 79.8(3) . . . . ? N5 Cu1 N4 C19 -100.2(3) 2_676 . . . ? N4 Cu1 N4 C19 -123(100) 2_676 . . . ? Cl1 Cu1 N4 C19 -8.3(3) . . . . ? N5 Cu1 N5 C2 -164(100) 2_676 . . . ? N4 Cu1 N5 C2 -72.5(3) . . . . ? N4 Cu1 N5 C2 107.5(3) 2_676 . . . ? Cl1 Cu1 N5 C2 16.6(3) . . . . ? N5 Cu1 N5 C1 21(100) 2_676 . . . ? N4 Cu1 N5 C1 112.1(3) . . . . ? N4 Cu1 N5 C1 -67.9(3) 2_676 . . . ? Cl1 Cu1 N5 C1 -158.8(3) . . . . ? C2 N6 N7 C1 0.0(4) . . . . ? C3 N6 N7 C1 176.8(3) . . . . ? C20 N3 N8 C19 0.7(4) . . . . ? C18 N3 N8 C19 177.5(3) . . . . ? N6 N7 C1 N5 -0.6(4) . . . . ? C2 N5 C1 N7 1.0(4) . . . . ? Cu1 N5 C1 N7 177.5(2) . . . . ? N7 N6 C2 N5 0.6(4) . . . . ? C3 N6 C2 N5 -175.8(3) . . . . ? C1 N5 C2 N6 -0.9(4) . . . . ? Cu1 N5 C2 N6 -177.1(2) . . . . ? C2 N6 C3 C4 115.0(4) . . . . ? N7 N6 C3 C4 -61.1(4) . . . . ? N6 C3 C4 C9 -40.5(4) . . . . ? N6 C3 C4 C5 141.2(3) . . . . ? C9 C4 C5 C6 -2.1(5) . . . . ? C3 C4 C5 C6 176.3(3) . . . . ? C4 C5 C6 C7 2.1(5) . . . . ? C5 C6 C7 C8 -1.1(5) . . . . ? C6 C7 C8 C9 0.1(5) . . . . ? C6 C7 C8 C10 179.8(3) . . . . ? C7 C8 C9 C4 -0.1(5) . . . . ? C10 C8 C9 C4 -179.8(3) . . . . ? C5 C4 C9 C8 1.1(5) . . . . ? C3 C4 C9 C8 -177.3(3) . . . . ? N1 N2 C10 O1 0.3(4) . . . . ? N1 N2 C10 C8 -178.2(3) . . . . ? C9 C8 C10 N2 -175.4(3) . . . . ? C7 C8 C10 N2 4.9(5) . . . . ? C9 C8 C10 O1 6.2(5) . . . . ? C7 C8 C10 O1 -173.6(3) . . . . ? N2 N1 C11 O1 -0.1(4) . . . . ? N2 N1 C11 C12 179.7(3) . . . . ? N1 C11 C12 C17 176.1(3) . . . . ? O1 C11 C12 C17 -4.2(5) . . . . ? N1 C11 C12 C13 -3.5(5) . . . . ? O1 C11 C12 C13 176.2(3) . . . . ? C17 C12 C13 C14 -1.1(5) . . . . ? C11 C12 C13 C14 178.5(3) . . . . ? C12 C13 C14 C15 0.7(5) . . . . ? C13 C14 C15 C16 -0.2(5) . . . . ? C14 C15 C16 C17 0.1(5) . . . . ? C14 C15 C16 C18 179.4(3) . . . . ? C15 C16 C17 C12 -0.5(5) . . . . ? C18 C16 C17 C12 -179.8(3) . . . . ? C13 C12 C17 C16 1.0(5) . . . . ? C11 C12 C17 C16 -178.6(3) . . . . ? C20 N3 C18 C16 94.9(4) . . . . ? N8 N3 C18 C16 -81.3(4) . . . . ? C17 C16 C18 N3 -2.0(5) . . . . ? C15 C16 C18 N3 178.6(3) . . . . ? N3 N8 C19 N4 -0.2(4) . . . . ? C20 N4 C19 N8 -0.4(4) . . . . ? Cu1 N4 C19 N8 171.0(2) . . . . ? C19 N4 C20 N3 0.8(4) . . . . ? Cu1 N4 C20 N3 -170.9(2) . . . . ? N8 N3 C20 N4 -0.9(4) . . . . ? C18 N3 C20 N4 -177.4(3) . . . . ? N2 C10 O1 C11 -0.4(4) . . . . ? C8 C10 O1 C11 178.3(3) . . . . ? N1 C11 O1 C10 0.3(4) . . . . ? C12 C11 O1 C10 -179.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.349 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.066 data_4 _database_code_depnum_ccdc_archive 'CCDC 703041' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H32 Cd N18 O2 S2' _chemical_formula_weight 997.38 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 '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 8.184(3) _cell_length_b 12.132(5) _cell_length_c 12.476(5) _cell_angle_alpha 111.198(6) _cell_angle_beta 93.700(7) _cell_angle_gamma 102.697(7) _cell_volume 1112.5(8) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 936 _cell_measurement_theta_min 2.583 _cell_measurement_theta_max 19.421 _exptl_crystal_description plan _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 506 _exptl_absorpt_coefficient_mu 0.644 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7604 _exptl_absorpt_correction_T_max 0.9624 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5377 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0830 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.09 _reflns_number_total 3864 _reflns_number_gt 2996 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3864 _refine_ls_number_parameters 295 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1222 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 Cd1 Cd 0.0000 0.5000 0.0000 0.0441(2) Uani 1 2 d S . . N1 N -0.0032(5) 0.5467(3) 0.2002(3) 0.0471(10) Uani 1 1 d . . . N2 N -0.0844(5) 0.5849(3) 0.3676(3) 0.0412(10) Uani 1 1 d . . . N3 N 0.0621(6) 0.5529(4) 0.3798(3) 0.0566(12) Uani 1 1 d . . . N4 N 0.2773(6) 1.1575(4) 0.6790(3) 0.0557(12) Uani 1 1 d . . . N5 N 0.3951(6) 1.2107(4) 0.6225(4) 0.0559(12) Uani 1 1 d . . . N6 N 0.3741(5) 0.8544(3) 0.0833(3) 0.0425(10) Uani 1 1 d . . . N7 N 0.2452(5) 0.8858(4) 0.0390(3) 0.0510(11) Uani 1 1 d . . . N8 N 0.1596(6) 0.6962(4) 0.0369(3) 0.0507(11) Uani 1 1 d . . . N9 N 0.2451(6) 0.4382(5) 0.0154(4) 0.0680(13) Uani 1 1 d . . . C1 C 0.1209(7) 0.7874(5) 0.0128(4) 0.0534(14) Uani 1 1 d . . . H1 H 0.0124 0.7810 -0.0204 0.064 Uiso 1 1 calc R . . C2 C 0.3220(7) 0.7420(4) 0.0815(4) 0.0501(13) Uani 1 1 d . . . H2 H 0.3897 0.7017 0.1077 0.060 Uiso 1 1 calc R . . C3 C 0.5430(6) 0.9378(4) 0.1260(4) 0.0498(13) Uani 1 1 d . . . H3A H 0.5812 0.9650 0.0655 0.060 Uiso 1 1 calc R . . H3B H 0.6210 0.8945 0.1432 0.060 Uiso 1 1 calc R . . C4 C 0.5469(6) 1.0481(4) 0.2341(4) 0.0413(11) Uani 1 1 d . . . C5 C 0.4616(6) 1.0368(4) 0.3235(4) 0.0399(11) Uani 1 1 d . . . H5 H 0.3935 0.9609 0.3147 0.048 Uiso 1 1 calc R . . C6 C 0.4763(6) 1.1373(4) 0.4261(4) 0.0432(12) Uani 1 1 d . . . C7 C 0.5801(6) 1.2503(4) 0.4401(5) 0.0531(14) Uani 1 1 d . . . H7 H 0.5929 1.3178 0.5093 0.064 Uiso 1 1 calc R . . C8 C 0.6637(7) 1.2617(5) 0.3510(5) 0.0616(16) Uani 1 1 d . . . H8 H 0.7318 1.3376 0.3597 0.074 Uiso 1 1 calc R . . C9 C 0.6476(6) 1.1621(5) 0.2490(5) 0.0538(14) Uani 1 1 d . . . H9 H 0.7048 1.1714 0.1895 0.065 Uiso 1 1 calc R . . C10 C 0.3852(6) 1.1269(4) 0.5197(4) 0.0441(12) Uani 1 1 d . . . C11 C 0.2076(6) 1.0465(4) 0.6063(4) 0.0446(12) Uani 1 1 d . . . C12 C 0.0806(6) 0.9529(4) 0.6244(4) 0.0424(12) Uani 1 1 d . . . C13 C 0.0221(7) 0.9808(5) 0.7308(4) 0.0549(14) Uani 1 1 d . . . H13 H 0.0589 1.0598 0.7876 0.066 Uiso 1 1 calc R . . C14 C -0.0894(7) 0.8919(5) 0.7517(4) 0.0596(15) Uani 1 1 d . . . H14 H -0.1255 0.9101 0.8239 0.071 Uiso 1 1 calc R . . C15 C -0.1490(7) 0.7759(5) 0.6671(4) 0.0516(13) Uani 1 1 d . . . H15 H -0.2252 0.7164 0.6825 0.062 Uiso 1 1 calc R . . C16 C -0.0963(6) 0.7463(4) 0.5578(4) 0.0430(12) Uani 1 1 d . . . C17 C 0.0201(6) 0.8362(4) 0.5378(4) 0.0428(12) Uani 1 1 d . . . H17 H 0.0578 0.8183 0.4661 0.051 Uiso 1 1 calc R . . C18 C -0.1749(7) 0.6211(4) 0.4667(4) 0.0502(13) Uani 1 1 d . . . H18A H -0.1821 0.5619 0.5028 0.060 Uiso 1 1 calc R . . H18B H -0.2897 0.6174 0.4379 0.060 Uiso 1 1 calc R . . C19 C -0.1207(7) 0.5808(4) 0.2619(4) 0.0482(13) Uani 1 1 d . . . H19 H -0.2156 0.5993 0.2347 0.058 Uiso 1 1 calc R . . C20 C 0.1047(7) 0.5309(5) 0.2765(4) 0.0573(14) Uani 1 1 d . . . H20 H 0.2023 0.5061 0.2569 0.069 Uiso 1 1 calc R . . C21 C 0.3238(7) 0.3985(5) 0.0662(5) 0.0571(15) Uani 1 1 d . . . O1 O 0.2691(4) 1.0199(3) 0.5032(2) 0.0415(8) Uani 1 1 d . . . S1 S 0.4300(3) 0.3438(2) 0.14040(18) 0.1006(7) 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 Cd1 0.0566(4) 0.0390(3) 0.0306(3) 0.0117(2) 0.0039(2) 0.0042(2) N1 0.052(3) 0.057(3) 0.035(2) 0.018(2) 0.007(2) 0.020(2) N2 0.050(3) 0.041(2) 0.037(2) 0.0164(18) 0.0110(19) 0.0172(19) N3 0.068(3) 0.072(3) 0.039(2) 0.020(2) 0.009(2) 0.038(2) N4 0.076(3) 0.047(3) 0.041(2) 0.009(2) 0.006(2) 0.024(2) N5 0.072(3) 0.044(3) 0.045(2) 0.008(2) 0.001(2) 0.018(2) N6 0.047(3) 0.043(2) 0.033(2) 0.0123(18) 0.0036(19) 0.0081(19) N7 0.054(3) 0.051(3) 0.049(3) 0.025(2) -0.002(2) 0.008(2) N8 0.055(3) 0.044(3) 0.045(2) 0.014(2) 0.006(2) 0.003(2) N9 0.062(3) 0.081(4) 0.070(3) 0.034(3) 0.017(3) 0.026(3) C1 0.051(3) 0.055(3) 0.046(3) 0.016(3) -0.004(3) 0.008(3) C2 0.059(4) 0.042(3) 0.053(3) 0.022(3) 0.012(3) 0.014(3) C3 0.044(3) 0.057(3) 0.050(3) 0.027(3) 0.007(2) 0.005(2) C4 0.037(3) 0.042(3) 0.046(3) 0.020(2) -0.005(2) 0.009(2) C5 0.036(3) 0.041(3) 0.044(3) 0.022(2) -0.006(2) 0.005(2) C6 0.044(3) 0.038(3) 0.042(3) 0.011(2) -0.003(2) 0.011(2) C7 0.048(3) 0.042(3) 0.059(3) 0.011(3) -0.008(3) 0.009(2) C8 0.053(4) 0.046(3) 0.085(4) 0.030(3) 0.006(3) 0.006(3) C9 0.053(4) 0.048(3) 0.063(3) 0.029(3) 0.005(3) 0.007(3) C10 0.048(3) 0.035(3) 0.044(3) 0.010(2) -0.004(2) 0.014(2) C11 0.053(3) 0.050(3) 0.032(3) 0.012(2) 0.000(2) 0.026(3) C12 0.042(3) 0.055(3) 0.035(3) 0.015(2) 0.008(2) 0.026(2) C13 0.056(4) 0.066(4) 0.039(3) 0.009(3) 0.008(3) 0.027(3) C14 0.066(4) 0.086(4) 0.032(3) 0.017(3) 0.022(3) 0.035(3) C15 0.050(3) 0.072(4) 0.047(3) 0.031(3) 0.018(3) 0.026(3) C16 0.048(3) 0.054(3) 0.039(3) 0.022(2) 0.014(2) 0.027(2) C17 0.053(3) 0.056(3) 0.031(2) 0.021(2) 0.015(2) 0.029(2) C18 0.061(4) 0.052(3) 0.053(3) 0.029(3) 0.031(3) 0.024(3) C19 0.051(3) 0.054(3) 0.045(3) 0.023(3) 0.005(3) 0.020(3) C20 0.061(4) 0.077(4) 0.041(3) 0.020(3) 0.016(3) 0.034(3) C21 0.054(4) 0.061(4) 0.064(4) 0.024(3) 0.031(3) 0.022(3) O1 0.049(2) 0.0373(18) 0.0364(18) 0.0104(14) 0.0026(15) 0.0151(15) S1 0.1075(16) 0.1515(19) 0.1091(15) 0.0887(14) 0.0596(13) 0.0863(14) _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 Cd1 N9 2.310(5) 2_565 ? Cd1 N9 2.310(6) . ? Cd1 N8 2.312(4) . ? Cd1 N8 2.312(4) 2_565 ? Cd1 N1 2.356(4) . ? Cd1 N1 2.356(4) 2_565 ? N1 C19 1.315(6) . ? N1 C20 1.349(6) . ? N2 C19 1.314(6) . ? N2 N3 1.355(5) . ? N2 C18 1.462(5) . ? N3 C20 1.306(6) . ? N4 C11 1.294(6) . ? N4 N5 1.410(6) . ? N5 C10 1.300(6) . ? N6 C2 1.327(6) . ? N6 N7 1.348(5) . ? N6 C3 1.456(6) . ? N7 C1 1.307(6) . ? N8 C2 1.320(6) . ? N8 C1 1.340(6) . ? N9 C21 1.164(7) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.510(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.386(6) . ? C4 C9 1.386(6) . ? C5 C6 1.387(6) . ? C5 H5 0.9300 . ? C6 C7 1.388(6) . ? C6 C10 1.454(6) . ? C7 C8 1.376(7) . ? C7 H7 0.9300 . ? C8 C9 1.376(7) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 O1 1.367(5) . ? C11 O1 1.366(5) . ? C11 C12 1.455(7) . ? C12 C13 1.391(6) . ? C12 C17 1.391(6) . ? C13 C14 1.366(7) . ? C13 H13 0.9300 . ? C14 C15 1.376(7) . ? C14 H14 0.9300 . ? C15 C16 1.401(6) . ? C15 H15 0.9300 . ? C16 C17 1.390(6) . ? C16 C18 1.497(6) . ? C17 H17 0.9300 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 S1 1.627(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N9 Cd1 N9 180.00 2_565 . ? N9 Cd1 N8 89.74(17) 2_565 . ? N9 Cd1 N8 90.26(17) . . ? N9 Cd1 N8 90.26(17) 2_565 2_565 ? N9 Cd1 N8 89.74(17) . 2_565 ? N8 Cd1 N8 180.00 . 2_565 ? N9 Cd1 N1 90.65(16) 2_565 . ? N9 Cd1 N1 89.35(16) . . ? N8 Cd1 N1 91.45(13) . . ? N8 Cd1 N1 88.55(13) 2_565 . ? N9 Cd1 N1 89.35(16) 2_565 2_565 ? N9 Cd1 N1 90.65(16) . 2_565 ? N8 Cd1 N1 88.55(13) . 2_565 ? N8 Cd1 N1 91.45(13) 2_565 2_565 ? N1 Cd1 N1 180.00 . 2_565 ? C19 N1 C20 102.8(4) . . ? C19 N1 Cd1 128.5(3) . . ? C20 N1 Cd1 128.3(3) . . ? C19 N2 N3 110.6(4) . . ? C19 N2 C18 129.4(5) . . ? N3 N2 C18 119.9(4) . . ? C20 N3 N2 101.6(4) . . ? C11 N4 N5 106.3(4) . . ? C10 N5 N4 106.3(4) . . ? C2 N6 N7 110.4(4) . . ? C2 N6 C3 127.8(5) . . ? N7 N6 C3 121.8(4) . . ? C1 N7 N6 101.6(4) . . ? C2 N8 C1 102.5(4) . . ? C2 N8 Cd1 126.2(4) . . ? C1 N8 Cd1 131.1(4) . . ? C21 N9 Cd1 145.2(4) . . ? N7 C1 N8 115.7(5) . . ? N7 C1 H1 122.1 . . ? N8 C1 H1 122.1 . . ? N8 C2 N6 109.7(5) . . ? N8 C2 H2 125.1 . . ? N6 C2 H2 125.1 . . ? N6 C3 C4 112.2(4) . . ? N6 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N6 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C9 118.6(4) . . ? C5 C4 C3 121.4(4) . . ? C9 C4 C3 119.8(4) . . ? C4 C5 C6 121.0(4) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C7 119.6(5) . . ? C5 C6 C10 121.4(4) . . ? C7 C6 C10 119.0(4) . . ? C8 C7 C6 119.5(5) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 120.8(5) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C8 C9 C4 120.6(5) . . ? C8 C9 H9 119.7 . . ? C4 C9 H9 119.7 . . ? N5 C10 O1 112.1(4) . . ? N5 C10 C6 127.9(5) . . ? O1 C10 C6 120.0(4) . . ? N4 C11 O1 112.4(4) . . ? N4 C11 C12 127.7(4) . . ? O1 C11 C12 119.9(4) . . ? C13 C12 C17 120.1(5) . . ? C13 C12 C11 119.1(4) . . ? C17 C12 C11 120.8(4) . . ? C14 C13 C12 119.8(5) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.6(4) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C16 120.7(5) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 118.5(4) . . ? C17 C16 C18 123.3(4) . . ? C15 C16 C18 118.1(4) . . ? C16 C17 C12 120.2(4) . . ? C16 C17 H17 119.9 . . ? C12 C17 H17 119.9 . . ? N2 C18 C16 115.0(4) . . ? N2 C18 H18A 108.5 . . ? C16 C18 H18A 108.5 . . ? N2 C18 H18B 108.5 . . ? C16 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? N2 C19 N1 109.9(5) . . ? N2 C19 H19 125.0 . . ? N1 C19 H19 125.0 . . ? N3 C20 N1 115.0(5) . . ? N3 C20 H20 122.5 . . ? N1 C20 H20 122.5 . . ? N9 C21 S1 178.2(5) . . ? C11 O1 C10 102.9(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 N9 Cd1 N1 C19 6.4(4) 2_565 . . . ? N9 Cd1 N1 C19 -173.6(4) . . . . ? N8 Cd1 N1 C19 96.1(4) . . . . ? N8 Cd1 N1 C19 -83.9(4) 2_565 . . . ? N1 Cd1 N1 C19 -145(100) 2_565 . . . ? N9 Cd1 N1 C20 177.5(4) 2_565 . . . ? N9 Cd1 N1 C20 -2.5(4) . . . . ? N8 Cd1 N1 C20 -92.7(4) . . . . ? N8 Cd1 N1 C20 87.3(4) 2_565 . . . ? N1 Cd1 N1 C20 26(100) 2_565 . . . ? C19 N2 N3 C20 -0.1(5) . . . . ? C18 N2 N3 C20 -178.3(4) . . . . ? C11 N4 N5 C10 0.4(5) . . . . ? C2 N6 N7 C1 0.0(5) . . . . ? C3 N6 N7 C1 -179.7(4) . . . . ? N9 Cd1 N8 C2 163.8(4) 2_565 . . . ? N9 Cd1 N8 C2 -16.2(4) . . . . ? N8 Cd1 N8 C2 -15(66) 2_565 . . . ? N1 Cd1 N8 C2 73.2(4) . . . . ? N1 Cd1 N8 C2 -106.8(4) 2_565 . . . ? N9 Cd1 N8 C1 -21.6(4) 2_565 . . . ? N9 Cd1 N8 C1 158.4(4) . . . . ? N8 Cd1 N8 C1 160(66) 2_565 . . . ? N1 Cd1 N8 C1 -112.3(4) . . . . ? N1 Cd1 N8 C1 67.7(4) 2_565 . . . ? N9 Cd1 N9 C21 -165(100) 2_565 . . . ? N8 Cd1 N9 C21 118.9(8) . . . . ? N8 Cd1 N9 C21 -61.1(8) 2_565 . . . ? N1 Cd1 N9 C21 27.4(8) . . . . ? N1 Cd1 N9 C21 -152.6(8) 2_565 . . . ? N6 N7 C1 N8 0.1(6) . . . . ? C2 N8 C1 N7 -0.1(6) . . . . ? Cd1 N8 C1 N7 -175.6(3) . . . . ? C1 N8 C2 N6 0.1(5) . . . . ? Cd1 N8 C2 N6 175.9(3) . . . . ? N7 N6 C2 N8 -0.1(5) . . . . ? C3 N6 C2 N8 179.6(4) . . . . ? C2 N6 C3 C4 -112.3(5) . . . . ? N7 N6 C3 C4 67.3(5) . . . . ? N6 C3 C4 C5 42.9(6) . . . . ? N6 C3 C4 C9 -142.0(5) . . . . ? C9 C4 C5 C6 0.0(7) . . . . ? C3 C4 C5 C6 175.1(4) . . . . ? C4 C5 C6 C7 -1.0(7) . . . . ? C4 C5 C6 C10 179.0(4) . . . . ? C5 C6 C7 C8 1.5(8) . . . . ? C10 C6 C7 C8 -178.5(5) . . . . ? C6 C7 C8 C9 -1.0(8) . . . . ? C7 C8 C9 C4 -0.1(8) . . . . ? C5 C4 C9 C8 0.6(8) . . . . ? C3 C4 C9 C8 -174.6(5) . . . . ? N4 N5 C10 O1 -0.4(5) . . . . ? N4 N5 C10 C6 177.6(5) . . . . ? C5 C6 C10 N5 175.4(5) . . . . ? C7 C6 C10 N5 -4.6(8) . . . . ? C5 C6 C10 O1 -6.8(7) . . . . ? C7 C6 C10 O1 173.2(4) . . . . ? N5 N4 C11 O1 -0.2(5) . . . . ? N5 N4 C11 C12 178.3(5) . . . . ? N4 C11 C12 C13 0.1(8) . . . . ? O1 C11 C12 C13 178.6(4) . . . . ? N4 C11 C12 C17 -178.7(5) . . . . ? O1 C11 C12 C17 -0.2(7) . . . . ? C17 C12 C13 C14 2.7(8) . . . . ? C11 C12 C13 C14 -176.1(5) . . . . ? C12 C13 C14 C15 -2.2(8) . . . . ? C13 C14 C15 C16 0.2(8) . . . . ? C14 C15 C16 C17 1.2(7) . . . . ? C14 C15 C16 C18 -175.8(5) . . . . ? C15 C16 C17 C12 -0.7(7) . . . . ? C18 C16 C17 C12 176.2(5) . . . . ? C13 C12 C17 C16 -1.3(7) . . . . ? C11 C12 C17 C16 177.5(4) . . . . ? C19 N2 C18 C16 -103.1(6) . . . . ? N3 N2 C18 C16 74.7(5) . . . . ? C17 C16 C18 N2 18.8(7) . . . . ? C15 C16 C18 N2 -164.4(4) . . . . ? N3 N2 C19 N1 0.0(5) . . . . ? C18 N2 C19 N1 178.0(4) . . . . ? C20 N1 C19 N2 0.1(5) . . . . ? Cd1 N1 C19 N2 172.9(3) . . . . ? N2 N3 C20 N1 0.1(6) . . . . ? C19 N1 C20 N3 -0.1(6) . . . . ? Cd1 N1 C20 N3 -173.0(3) . . . . ? Cd1 N9 C21 S1 -12(19) . . . . ? N4 C11 O1 C10 0.0(5) . . . . ? C12 C11 O1 C10 -178.7(4) . . . . ? N5 C10 O1 C11 0.3(5) . . . . ? C6 C10 O1 C11 -177.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.09 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.629 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.079 data_5 _database_code_depnum_ccdc_archive 'CCDC 703042' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 Cd N10 O S2' _chemical_formula_weight 612.97 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 '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 9.915(2) _cell_length_b 11.385(3) _cell_length_c 11.494(3) _cell_angle_alpha 82.080(3) _cell_angle_beta 81.354(3) _cell_angle_gamma 72.722(3) _cell_volume 1218.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2992 _cell_measurement_theta_min 2.474 _cell_measurement_theta_max 27.406 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.670 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 1.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5666 _exptl_absorpt_correction_T_max 0.7696 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5801 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.10 _reflns_number_total 4230 _reflns_number_gt 3809 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+0.0805P] 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 4230 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0767 _refine_ls_wR_factor_gt 0.0745 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 Cd1 Cd 0.74253(2) 0.97227(2) 0.598627(18) 0.03751(9) Uani 1 1 d . . . N1 N 0.7541(3) 0.2908(2) 1.0799(2) 0.0488(7) Uani 1 1 d . . . N2 N 0.8354(3) 0.3324(3) 1.1463(2) 0.0497(7) Uani 1 1 d . . . N3 N 0.8371(2) 0.8950(2) 0.9720(2) 0.0376(6) Uani 1 1 d . . . N4 N 0.7544(3) 0.9344(2) 0.8021(2) 0.0407(6) Uani 1 1 d . . . N5 N 0.5611(3) 0.6554(2) 0.6140(2) 0.0396(6) Uani 1 1 d . . . N6 N 0.6837(3) 0.7861(2) 0.6006(2) 0.0453(6) Uani 1 1 d . . . N7 N 0.4977(3) 1.0575(3) 0.6435(2) 0.0499(7) Uani 1 1 d . . . N8 N 0.9813(3) 0.8587(3) 0.5812(3) 0.0527(7) Uani 1 1 d . . . N9 N 0.6928(3) 0.9294(2) 0.9978(2) 0.0446(6) Uani 1 1 d . . . N10 N 0.6776(3) 0.6099(3) 0.5382(2) 0.0506(7) Uani 1 1 d . . . C1 C 0.7084(3) 0.3799(3) 1.0014(3) 0.0392(7) Uani 1 1 d . . . C2 C 0.6200(3) 0.3817(3) 0.9108(3) 0.0376(7) Uani 1 1 d . . . C3 C 0.5703(3) 0.2797(3) 0.9091(3) 0.0480(8) Uani 1 1 d . . . H3 H 0.5935 0.2123 0.9656 0.058 Uiso 1 1 calc R . . C4 C 0.4870(4) 0.2785(3) 0.8240(3) 0.0521(9) Uani 1 1 d . . . H4 H 0.4534 0.2105 0.8236 0.063 Uiso 1 1 calc R . . C5 C 0.4530(3) 0.3770(3) 0.7397(3) 0.0453(8) Uani 1 1 d . . . H5 H 0.3984 0.3745 0.6815 0.054 Uiso 1 1 calc R . . C6 C 0.4996(3) 0.4806(3) 0.7406(3) 0.0386(7) Uani 1 1 d . . . C7 C 0.5839(3) 0.4817(3) 0.8266(3) 0.0387(7) Uani 1 1 d . . . H7 H 0.6164 0.5502 0.8276 0.046 Uiso 1 1 calc R . . C8 C 0.4532(3) 0.5894(3) 0.6509(3) 0.0479(8) Uani 1 1 d . . . H8A H 0.4318 0.5608 0.5820 0.057 Uiso 1 1 calc R . . H8B H 0.3666 0.6462 0.6843 0.057 Uiso 1 1 calc R . . C9 C 0.5672(3) 0.7580(3) 0.6499(3) 0.0454(8) Uani 1 1 d . . . H9 H 0.4986 0.8045 0.7029 0.055 Uiso 1 1 calc R . . C10 C 0.7461(4) 0.6934(3) 0.5324(3) 0.0498(8) Uani 1 1 d . . . H10 H 0.8316 0.6887 0.4846 0.060 Uiso 1 1 calc R . . C11 C 0.8304(3) 0.4442(3) 1.1026(3) 0.0400(7) Uani 1 1 d . . . C12 C 0.8958(3) 0.5286(3) 1.1407(3) 0.0392(7) Uani 1 1 d . . . C13 C 0.8799(3) 0.6476(3) 1.0846(3) 0.0391(7) Uani 1 1 d . . . H13 H 0.8281 0.6735 1.0201 0.047 Uiso 1 1 calc R . . C14 C 0.9405(3) 0.7277(3) 1.1237(3) 0.0389(7) Uani 1 1 d . . . C15 C 0.9286(3) 0.8567(3) 1.0659(3) 0.0454(8) Uani 1 1 d . . . H15A H 0.8925 0.9140 1.1260 0.054 Uiso 1 1 calc R . . H15B H 1.0229 0.8623 1.0338 0.054 Uiso 1 1 calc R . . C16 C 1.0173(3) 0.6871(3) 1.2203(3) 0.0500(8) Uani 1 1 d . . . H16 H 1.0575 0.7404 1.2481 0.060 Uiso 1 1 calc R . . C17 C 1.0347(4) 0.5699(4) 1.2752(3) 0.0554(9) Uani 1 1 d . . . H17 H 1.0880 0.5442 1.3389 0.066 Uiso 1 1 calc R . . C18 C 0.9746(3) 0.4897(3) 1.2375(3) 0.0503(8) Uani 1 1 d . . . H18 H 0.9859 0.4104 1.2758 0.060 Uiso 1 1 calc R . . C19 C 0.6495(3) 0.9516(3) 0.8924(3) 0.0430(7) Uani 1 1 d . . . H19 H 0.5538 0.9772 0.8811 0.052 Uiso 1 1 calc R . . C20 C 0.8707(3) 0.8982(3) 0.8558(3) 0.0414(7) Uani 1 1 d . . . H20 H 0.9630 0.8778 0.8176 0.050 Uiso 1 1 calc R . . C21 C 0.3874(3) 1.0425(3) 0.6433(3) 0.0402(7) Uani 1 1 d . . . C22 C 1.0812(3) 0.8356(3) 0.5142(3) 0.0405(7) Uani 1 1 d . . . O1 O 0.7520(2) 0.48088(18) 1.00941(17) 0.0378(5) Uani 1 1 d . . . S1 S 1.22476(9) 0.80146(8) 0.41845(8) 0.0510(2) Uani 1 1 d . . . S2 S 0.23298(9) 1.01661(9) 0.64297(7) 0.0506(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 Cd1 0.03450(14) 0.04705(15) 0.03307(14) 0.00048(10) -0.00490(9) -0.01619(10) N1 0.0499(17) 0.0428(16) 0.0514(17) 0.0041(13) -0.0106(13) -0.0111(13) N2 0.0506(17) 0.0471(17) 0.0470(17) 0.0066(13) -0.0117(13) -0.0090(13) N3 0.0374(14) 0.0405(14) 0.0334(14) -0.0042(11) -0.0044(11) -0.0080(11) N4 0.0357(14) 0.0492(16) 0.0327(14) -0.0012(12) -0.0034(11) -0.0068(12) N5 0.0443(15) 0.0417(15) 0.0340(14) 0.0028(11) -0.0062(11) -0.0162(12) N6 0.0462(16) 0.0500(16) 0.0412(15) -0.0033(13) 0.0012(12) -0.0195(13) N7 0.0391(16) 0.0621(19) 0.0539(18) -0.0156(14) -0.0067(13) -0.0171(14) N8 0.0359(15) 0.0641(19) 0.0530(18) 0.0032(15) 0.0001(13) -0.0132(14) N9 0.0424(15) 0.0499(16) 0.0349(15) -0.0038(12) 0.0008(12) -0.0056(12) N10 0.0564(18) 0.0516(17) 0.0436(16) -0.0093(13) 0.0056(13) -0.0184(14) C1 0.0378(17) 0.0346(16) 0.0413(17) -0.0005(14) -0.0016(13) -0.0072(13) C2 0.0373(16) 0.0370(16) 0.0373(17) -0.0040(13) -0.0007(13) -0.0103(13) C3 0.053(2) 0.0358(17) 0.052(2) 0.0012(15) -0.0020(16) -0.0118(15) C4 0.058(2) 0.0426(19) 0.063(2) -0.0091(17) -0.0029(18) -0.0247(17) C5 0.0441(18) 0.053(2) 0.0438(19) -0.0125(16) -0.0005(14) -0.0203(16) C6 0.0350(16) 0.0435(18) 0.0377(17) -0.0035(14) 0.0025(13) -0.0153(14) C7 0.0407(17) 0.0356(16) 0.0427(18) -0.0041(14) -0.0025(13) -0.0163(13) C8 0.0451(19) 0.058(2) 0.0459(19) 0.0052(16) -0.0102(15) -0.0242(16) C9 0.050(2) 0.0418(18) 0.0401(18) -0.0017(14) 0.0025(15) -0.0114(15) C10 0.0443(19) 0.054(2) 0.048(2) -0.0032(17) 0.0044(15) -0.0143(16) C11 0.0332(16) 0.0461(19) 0.0344(17) 0.0009(14) -0.0021(13) -0.0045(14) C12 0.0316(16) 0.0486(18) 0.0322(16) -0.0017(14) -0.0025(12) -0.0050(14) C13 0.0335(16) 0.0524(19) 0.0287(15) -0.0030(14) -0.0065(12) -0.0073(14) C14 0.0325(16) 0.0507(19) 0.0304(16) -0.0070(14) -0.0028(12) -0.0061(14) C15 0.0490(19) 0.052(2) 0.0395(18) -0.0091(15) -0.0126(14) -0.0143(15) C16 0.0457(19) 0.064(2) 0.0414(19) -0.0039(17) -0.0158(15) -0.0126(17) C17 0.049(2) 0.075(3) 0.0395(19) 0.0015(18) -0.0224(15) -0.0087(18) C18 0.0456(19) 0.060(2) 0.0395(18) 0.0069(16) -0.0117(15) -0.0077(16) C19 0.0358(17) 0.0438(18) 0.0430(19) 0.0016(15) -0.0044(14) -0.0041(14) C20 0.0379(17) 0.0472(19) 0.0357(17) -0.0039(14) 0.0004(13) -0.0091(14) C21 0.0436(19) 0.0453(18) 0.0294(16) -0.0057(13) -0.0056(13) -0.0075(15) C22 0.0389(18) 0.0462(18) 0.0398(18) 0.0011(14) -0.0114(14) -0.0161(14) O1 0.0390(12) 0.0354(11) 0.0373(11) 0.0034(9) -0.0082(9) -0.0088(9) S1 0.0476(5) 0.0511(5) 0.0547(5) -0.0137(4) 0.0077(4) -0.0175(4) S2 0.0440(5) 0.0804(6) 0.0347(4) -0.0061(4) -0.0019(3) -0.0300(4) _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 Cd1 N8 2.329(3) . ? Cd1 N4 2.334(2) . ? Cd1 N7 2.337(3) . ? Cd1 N6 2.356(3) . ? Cd1 S1 2.6678(10) 2_776 ? Cd1 S2 2.7395(10) 2_676 ? N1 C1 1.282(4) . ? N1 N2 1.403(4) . ? N2 C11 1.292(4) . ? N3 C20 1.325(4) . ? N3 N9 1.364(3) . ? N3 C15 1.452(4) . ? N4 C20 1.320(4) . ? N4 C19 1.345(4) . ? N5 C9 1.312(4) . ? N5 N10 1.352(3) . ? N5 C8 1.464(4) . ? N6 C9 1.316(4) . ? N6 C10 1.343(4) . ? N7 C21 1.157(4) . ? N8 C22 1.147(4) . ? N9 C19 1.313(4) . ? N10 C10 1.313(4) . ? C1 O1 1.361(3) . ? C1 C2 1.454(4) . ? C2 C7 1.385(4) . ? C2 C3 1.393(4) . ? C3 C4 1.376(5) . ? C3 H3 0.9300 . ? C4 C5 1.373(5) . ? C4 H4 0.9300 . ? C5 C6 1.390(4) . ? C5 H5 0.9300 . ? C6 C7 1.390(4) . ? C6 C8 1.505(4) . ? C7 H7 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 O1 1.363(4) . ? C11 C12 1.452(4) . ? C12 C13 1.392(4) . ? C12 C18 1.401(4) . ? C13 C14 1.383(4) . ? C13 H13 0.9300 . ? C14 C16 1.390(4) . ? C14 C15 1.505(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.368(5) . ? C16 H16 0.9300 . ? C17 C18 1.375(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 S2 1.643(3) . ? C22 S1 1.646(3) . ? S1 Cd1 2.6678(10) 2_776 ? S2 Cd1 2.7395(10) 2_676 ? 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 Cd1 N4 85.32(9) . . ? N8 Cd1 N7 169.43(10) . . ? N4 Cd1 N7 86.99(9) . . ? N8 Cd1 N6 88.24(10) . . ? N4 Cd1 N6 89.91(9) . . ? N7 Cd1 N6 84.50(10) . . ? N8 Cd1 S1 98.81(7) . 2_776 ? N4 Cd1 S1 94.88(7) . 2_776 ? N7 Cd1 S1 89.06(7) . 2_776 ? N6 Cd1 S1 171.76(7) . 2_776 ? N8 Cd1 S2 85.88(7) . 2_676 ? N4 Cd1 S2 170.55(6) . 2_676 ? N7 Cd1 S2 101.27(7) . 2_676 ? N6 Cd1 S2 86.37(7) . 2_676 ? S1 Cd1 S2 89.87(3) 2_776 2_676 ? C1 N1 N2 106.4(3) . . ? C11 N2 N1 106.4(3) . . ? C20 N3 N9 109.6(2) . . ? C20 N3 C15 129.8(3) . . ? N9 N3 C15 120.6(2) . . ? C20 N4 C19 103.2(3) . . ? C20 N4 Cd1 126.7(2) . . ? C19 N4 Cd1 130.0(2) . . ? C9 N5 N10 110.1(2) . . ? C9 N5 C8 128.2(3) . . ? N10 N5 C8 121.5(3) . . ? C9 N6 C10 102.3(3) . . ? C9 N6 Cd1 128.4(2) . . ? C10 N6 Cd1 128.0(2) . . ? C21 N7 Cd1 144.4(3) . . ? C22 N8 Cd1 142.3(3) . . ? C19 N9 N3 102.3(2) . . ? C10 N10 N5 101.7(3) . . ? N1 C1 O1 112.5(3) . . ? N1 C1 C2 127.4(3) . . ? O1 C1 C2 120.1(3) . . ? C7 C2 C3 119.4(3) . . ? C7 C2 C1 121.9(3) . . ? C3 C2 C1 118.7(3) . . ? C4 C3 C2 120.0(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.5(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.5(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C7 119.0(3) . . ? C5 C6 C8 118.8(3) . . ? C7 C6 C8 122.2(3) . . ? C2 C7 C6 120.6(3) . . ? C2 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? N5 C8 C6 112.7(3) . . ? N5 C8 H8A 109.0 . . ? C6 C8 H8A 109.0 . . ? N5 C8 H8B 109.0 . . ? C6 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? N5 C9 N6 110.6(3) . . ? N5 C9 H9 124.7 . . ? N6 C9 H9 124.7 . . ? N10 C10 N6 115.1(3) . . ? N10 C10 H10 122.4 . . ? N6 C10 H10 122.4 . . ? N2 C11 O1 112.0(3) . . ? N2 C11 C12 128.2(3) . . ? O1 C11 C12 119.9(3) . . ? C13 C12 C18 119.5(3) . . ? C13 C12 C11 121.5(3) . . ? C18 C12 C11 119.0(3) . . ? C14 C13 C12 120.7(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C16 118.7(3) . . ? C13 C14 C15 123.2(3) . . ? C16 C14 C15 118.1(3) . . ? N3 C15 C14 114.5(3) . . ? N3 C15 H15A 108.6 . . ? C14 C15 H15A 108.6 . . ? N3 C15 H15B 108.6 . . ? C14 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? C17 C16 C14 121.0(3) . . ? C17 C16 H16 119.5 . . ? C14 C16 H16 119.5 . . ? C16 C17 C18 120.8(3) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C17 C18 C12 119.2(3) . . ? C17 C18 H18 120.4 . . ? C12 C18 H18 120.4 . . ? N9 C19 N4 114.7(3) . . ? N9 C19 H19 122.6 . . ? N4 C19 H19 122.6 . . ? N4 C20 N3 110.2(3) . . ? N4 C20 H20 124.9 . . ? N3 C20 H20 124.9 . . ? N7 C21 S2 178.3(3) . . ? N8 C22 S1 179.7(4) . . ? C1 O1 C11 102.8(2) . . ? C22 S1 Cd1 93.32(11) . 2_776 ? C21 S2 Cd1 93.48(10) . 2_676 ? 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 C1 N1 N2 C11 0.7(3) . . . . ? N8 Cd1 N4 C20 17.4(3) . . . . ? N7 Cd1 N4 C20 -169.8(3) . . . . ? N6 Cd1 N4 C20 105.7(3) . . . . ? S1 Cd1 N4 C20 -81.0(3) 2_776 . . . ? S2 Cd1 N4 C20 39.0(6) 2_676 . . . ? N8 Cd1 N4 C19 -167.9(3) . . . . ? N7 Cd1 N4 C19 4.8(3) . . . . ? N6 Cd1 N4 C19 -79.7(3) . . . . ? S1 Cd1 N4 C19 93.6(3) 2_776 . . . ? S2 Cd1 N4 C19 -146.4(3) 2_676 . . . ? N8 Cd1 N6 C9 152.6(3) . . . . ? N4 Cd1 N6 C9 67.3(3) . . . . ? N7 Cd1 N6 C9 -19.7(3) . . . . ? S1 Cd1 N6 C9 -58.4(6) 2_776 . . . ? S2 Cd1 N6 C9 -121.4(3) 2_676 . . . ? N8 Cd1 N6 C10 -42.5(3) . . . . ? N4 Cd1 N6 C10 -127.8(3) . . . . ? N7 Cd1 N6 C10 145.2(3) . . . . ? S1 Cd1 N6 C10 106.5(5) 2_776 . . . ? S2 Cd1 N6 C10 43.5(3) 2_676 . . . ? N8 Cd1 N7 C21 -64.6(7) . . . . ? N4 Cd1 N7 C21 -107.9(4) . . . . ? N6 Cd1 N7 C21 -17.7(4) . . . . ? S1 Cd1 N7 C21 157.1(4) 2_776 . . . ? S2 Cd1 N7 C21 67.4(4) 2_676 . . . ? N4 Cd1 N8 C22 -166.5(4) . . . . ? N7 Cd1 N8 C22 150.0(5) . . . . ? N6 Cd1 N8 C22 103.4(4) . . . . ? S1 Cd1 N8 C22 -72.3(4) 2_776 . . . ? S2 Cd1 N8 C22 16.9(4) 2_676 . . . ? C20 N3 N9 C19 -0.2(3) . . . . ? C15 N3 N9 C19 -177.4(3) . . . . ? C9 N5 N10 C10 -1.3(3) . . . . ? C8 N5 N10 C10 -178.0(3) . . . . ? N2 N1 C1 O1 -0.4(3) . . . . ? N2 N1 C1 C2 179.6(3) . . . . ? N1 C1 C2 C7 -176.4(3) . . . . ? O1 C1 C2 C7 3.6(4) . . . . ? N1 C1 C2 C3 3.7(5) . . . . ? O1 C1 C2 C3 -176.4(3) . . . . ? C7 C2 C3 C4 0.4(5) . . . . ? C1 C2 C3 C4 -179.7(3) . . . . ? C2 C3 C4 C5 0.5(5) . . . . ? C3 C4 C5 C6 -1.5(5) . . . . ? C4 C5 C6 C7 1.5(5) . . . . ? C4 C5 C6 C8 -176.6(3) . . . . ? C3 C2 C7 C6 -0.3(4) . . . . ? C1 C2 C7 C6 179.7(3) . . . . ? C5 C6 C7 C2 -0.6(4) . . . . ? C8 C6 C7 C2 177.4(3) . . . . ? C9 N5 C8 C6 -100.1(4) . . . . ? N10 N5 C8 C6 76.1(4) . . . . ? C5 C6 C8 N5 -147.0(3) . . . . ? C7 C6 C8 N5 35.0(4) . . . . ? N10 N5 C9 N6 0.6(4) . . . . ? C8 N5 C9 N6 177.1(3) . . . . ? C10 N6 C9 N5 0.3(4) . . . . ? Cd1 N6 C9 N5 168.2(2) . . . . ? N5 N10 C10 N6 1.5(4) . . . . ? C9 N6 C10 N10 -1.2(4) . . . . ? Cd1 N6 C10 N10 -169.1(2) . . . . ? N1 N2 C11 O1 -0.8(3) . . . . ? N1 N2 C11 C12 179.2(3) . . . . ? N2 C11 C12 C13 -179.6(3) . . . . ? O1 C11 C12 C13 0.4(4) . . . . ? N2 C11 C12 C18 -0.7(5) . . . . ? O1 C11 C12 C18 179.3(3) . . . . ? C18 C12 C13 C14 -0.3(4) . . . . ? C11 C12 C13 C14 178.6(3) . . . . ? C12 C13 C14 C16 -0.1(4) . . . . ? C12 C13 C14 C15 179.2(3) . . . . ? C20 N3 C15 C14 -99.6(4) . . . . ? N9 N3 C15 C14 77.0(3) . . . . ? C13 C14 C15 N3 5.4(4) . . . . ? C16 C14 C15 N3 -175.3(3) . . . . ? C13 C14 C16 C17 0.8(5) . . . . ? C15 C14 C16 C17 -178.6(3) . . . . ? C14 C16 C17 C18 -1.1(5) . . . . ? C16 C17 C18 C12 0.7(5) . . . . ? C13 C12 C18 C17 0.0(5) . . . . ? C11 C12 C18 C17 -178.9(3) . . . . ? N3 N9 C19 N4 -0.2(4) . . . . ? C20 N4 C19 N9 0.5(4) . . . . ? Cd1 N4 C19 N9 -175.1(2) . . . . ? C19 N4 C20 N3 -0.6(3) . . . . ? Cd1 N4 C20 N3 175.22(19) . . . . ? N9 N3 C20 N4 0.5(3) . . . . ? C15 N3 C20 N4 177.4(3) . . . . ? Cd1 N7 C21 S2 23(10) . . . . ? Cd1 N8 C22 S1 -147(100) . . . . ? N1 C1 O1 C11 -0.1(3) . . . . ? C2 C1 O1 C11 179.9(3) . . . . ? N2 C11 O1 C1 0.6(3) . . . . ? C12 C11 O1 C1 -179.4(3) . . . . ? N8 C22 S1 Cd1 -142(68) . . . 2_776 ? N7 C21 S2 Cd1 -89(10) . . . 2_676 ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.496 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.066 data_60928cm _database_code_depnum_ccdc_archive 'CCDC 703043' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H36 Co N18 O10' _chemical_formula_weight 987.80 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' O O 0.0106 0.0060 '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 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 23.327(5) _cell_length_b 9.0863(19) _cell_length_c 21.994(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.821(3) _cell_angle_gamma 90.00 _cell_volume 4264.7(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1359 _cell_measurement_theta_min 2.436 _cell_measurement_theta_max 20.415 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2036 _exptl_absorpt_coefficient_mu 0.485 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7662 _exptl_absorpt_correction_T_max 0.9396 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10388 _diffrn_reflns_av_R_equivalents 0.0658 _diffrn_reflns_av_sigmaI/netI 0.0850 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3785 _reflns_number_gt 2583 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0597P)^2^+1.1151P] 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 3785 _refine_ls_number_parameters 340 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1062 _refine_ls_R_factor_gt 0.0691 _refine_ls_wR_factor_ref 0.1451 _refine_ls_wR_factor_gt 0.1305 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.86951(18) 0.4434(6) 0.73971(19) 0.0413(12) Uani 1 1 d . . . H1 H 0.8857 0.5383 0.7487 0.050 Uiso 1 1 calc R . . H2B H 0.9411 0.1368 0.6573 0.062 Uiso 1 1 d RD . . C2 C 0.86481(19) 0.2154(5) 0.72386(18) 0.0351(11) Uani 1 1 d . . . H2 H 0.8744 0.1179 0.7190 0.042 Uiso 1 1 calc R . . C3 C 0.7513(2) 0.1809(6) 0.7014(2) 0.0457(13) Uani 1 1 d . . . H3A H 0.7305 0.2131 0.7294 0.055 Uiso 1 1 calc R . . H3B H 0.7611 0.0772 0.7102 0.055 Uiso 1 1 calc R . . C4 C 0.70715(18) 0.1998(5) 0.62954(19) 0.0330(11) Uani 1 1 d . . . C5 C 0.65161(19) 0.1224(6) 0.6074(2) 0.0420(12) Uani 1 1 d . . . H5 H 0.6429 0.0616 0.6366 0.050 Uiso 1 1 calc R . . C6 C 0.6089(2) 0.1345(6) 0.5424(2) 0.0476(14) Uani 1 1 d . . . H6 H 0.5717 0.0812 0.5279 0.057 Uiso 1 1 calc R . . C7 C 0.62088(19) 0.2239(5) 0.4994(2) 0.0416(12) Uani 1 1 d . . . H7 H 0.5919 0.2314 0.4555 0.050 Uiso 1 1 calc R . . C8 C 0.67614(18) 0.3041(5) 0.52044(18) 0.0299(10) Uani 1 1 d . . . C9 C 0.71948(17) 0.2901(5) 0.58637(18) 0.0288(10) Uani 1 1 d . . . H9 H 0.7569 0.3424 0.6010 0.035 Uiso 1 1 calc R . . C10 C 0.68733(17) 0.4019(5) 0.47537(19) 0.0296(10) Uani 1 1 d . . . C11 C 0.73305(19) 0.5646(5) 0.44033(19) 0.0323(11) Uani 1 1 d . . . C12 C 0.78142(19) 0.6676(5) 0.44354(19) 0.0330(10) Uani 1 1 d . . . C13 C 0.7753(2) 0.7488(5) 0.3879(2) 0.0406(12) Uani 1 1 d . . . H13 H 0.7396 0.7388 0.3488 0.049 Uiso 1 1 calc R . . C14 C 0.8221(2) 0.8443(5) 0.3906(2) 0.0448(13) Uani 1 1 d . . . H14 H 0.8179 0.8979 0.3530 0.054 Uiso 1 1 calc R . . C15 C 0.8754(2) 0.8613(5) 0.4488(2) 0.0433(12) Uani 1 1 d . . . H15 H 0.9071 0.9249 0.4499 0.052 Uiso 1 1 calc R . . C16 C 0.8817(2) 0.7839(5) 0.5054(2) 0.0351(11) Uani 1 1 d . . . C17 C 0.83489(19) 0.6877(5) 0.5026(2) 0.0365(11) Uani 1 1 d . . . H17 H 0.8389 0.6355 0.5404 0.044 Uiso 1 1 calc R . . C18 C 0.9379(2) 0.8081(5) 0.5703(2) 0.0439(12) Uani 1 1 d . . . H18A H 0.9708 0.8564 0.5614 0.053 Uiso 1 1 calc R . . H18B H 0.9261 0.8727 0.5984 0.053 Uiso 1 1 calc R . . C19 C 0.95984(18) 0.6199(5) 0.66075(19) 0.0329(11) Uani 1 1 d . . . H19 H 0.9430 0.6709 0.6863 0.040 Uiso 1 1 calc R . . C20 C 1.00196(17) 0.4635(5) 0.6234(2) 0.0341(11) Uani 1 1 d . . . H20 H 1.0214 0.3769 0.6193 0.041 Uiso 1 1 calc R . . Co1 Co 1.0000 0.32751(9) 0.7500 0.0300(3) Uani 1 2 d S . . N1 N 0.98486(14) 0.4874(4) 0.67484(15) 0.0306(9) Uani 1 1 d . . . N2 N 0.98936(15) 0.5696(4) 0.58049(16) 0.0349(9) Uani 1 1 d . . . N3 N 0.96198(15) 0.6704(4) 0.60542(16) 0.0334(9) Uani 1 1 d . . . N4 N 0.68132(16) 0.5334(4) 0.39008(16) 0.0389(10) Uani 1 1 d . . . N5 N 0.65128(15) 0.4269(4) 0.41258(15) 0.0358(9) Uani 1 1 d . . . N6 N 0.80930(16) 0.2628(5) 0.71914(15) 0.0377(9) Uani 1 1 d . . . N7 N 0.81112(16) 0.4120(5) 0.72924(16) 0.0431(10) Uani 1 1 d . . . N8 N 0.90431(15) 0.3257(4) 0.73630(15) 0.0344(9) Uani 1 1 d . . . N9 N 0.59336(19) 0.3769(5) 0.7096(2) 0.0448(11) Uani 0.370(14) 1 d PD A 1 N9' N 0.59336(19) 0.3769(5) 0.7096(2) 0.0448(11) Uani 0.630(14) 1 d PD A 2 O1 O 0.73986(12) 0.4855(3) 0.49546(12) 0.0296(7) Uani 1 1 d . . . O2 O 0.97937(12) 0.1596(3) 0.67637(13) 0.0439(8) Uani 1 1 d D . . H2A H 1.0050 0.0928 0.6906 0.066 Uiso 1 1 d RD . . O3 O 0.6520(4) 0.3688(18) 0.7243(5) 0.057(5) Uani 0.370(14) 1 d PD A 1 O4 O 0.5654(7) 0.299(2) 0.7290(6) 0.090(8) Uani 0.370(14) 1 d PD A 1 O5 O 0.5673(5) 0.4729(17) 0.6668(6) 0.052(4) Uani 0.370(14) 1 d PD A 1 O3' O 0.6241(4) 0.2667(9) 0.7376(3) 0.075(3) Uani 0.630(14) 1 d PD A 2 O4' O 0.5487(3) 0.4080(10) 0.7278(3) 0.051(2) Uani 0.630(14) 1 d PD A 2 O5' O 0.5997(8) 0.4602(13) 0.6704(7) 0.137(6) Uani 0.630(14) 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 C1 0.022(2) 0.061(4) 0.028(2) -0.015(2) -0.0036(19) -0.002(2) C2 0.026(2) 0.048(3) 0.018(2) 0.004(2) -0.0050(18) 0.004(2) C3 0.033(3) 0.072(4) 0.028(2) 0.000(2) 0.008(2) -0.015(2) C4 0.022(2) 0.054(3) 0.022(2) -0.005(2) 0.0069(18) -0.005(2) C5 0.033(3) 0.071(4) 0.026(2) -0.004(2) 0.016(2) -0.017(2) C6 0.027(3) 0.081(4) 0.029(2) -0.008(2) 0.006(2) -0.022(2) C7 0.027(2) 0.063(4) 0.023(2) -0.009(2) -0.0016(19) -0.008(2) C8 0.022(2) 0.040(3) 0.022(2) -0.0047(19) 0.0028(18) 0.0001(19) C9 0.013(2) 0.043(3) 0.023(2) -0.0084(19) 0.0003(17) -0.0015(18) C10 0.019(2) 0.035(3) 0.024(2) -0.0058(19) -0.0017(18) -0.0022(19) C11 0.034(3) 0.032(3) 0.023(2) 0.0007(19) 0.003(2) 0.001(2) C12 0.035(2) 0.034(3) 0.021(2) 0.003(2) 0.0013(18) 0.002(2) C13 0.043(3) 0.042(3) 0.028(2) -0.002(2) 0.005(2) -0.003(2) C14 0.059(3) 0.044(3) 0.027(2) 0.006(2) 0.014(2) 0.004(3) C15 0.051(3) 0.035(3) 0.039(3) 0.006(2) 0.013(2) -0.008(2) C16 0.036(3) 0.032(3) 0.032(2) 0.002(2) 0.007(2) -0.002(2) C17 0.039(3) 0.032(3) 0.029(2) 0.005(2) 0.004(2) 0.003(2) C18 0.038(3) 0.030(3) 0.049(3) 0.006(2) 0.001(2) -0.004(2) C19 0.025(2) 0.041(3) 0.024(2) -0.007(2) 0.0009(18) 0.001(2) C20 0.017(2) 0.044(3) 0.030(2) -0.005(2) -0.0023(19) 0.004(2) Co1 0.0154(4) 0.0398(6) 0.0215(4) 0.000 -0.0062(3) 0.000 N1 0.0208(18) 0.039(2) 0.0216(17) -0.0043(16) -0.0023(15) 0.0022(16) N2 0.0238(19) 0.047(3) 0.0289(19) -0.0053(19) 0.0057(16) 0.0004(17) N3 0.029(2) 0.037(2) 0.0272(19) -0.0033(18) 0.0043(16) -0.0038(17) N4 0.035(2) 0.042(2) 0.0219(18) 0.0009(17) -0.0075(16) -0.0015(18) N5 0.030(2) 0.042(2) 0.0225(18) 0.0008(17) -0.0033(16) -0.0022(17) N6 0.024(2) 0.065(3) 0.0177(18) 0.0008(19) 0.0022(15) -0.0036(19) N7 0.026(2) 0.067(3) 0.027(2) -0.012(2) 0.0024(17) 0.002(2) N8 0.0203(18) 0.046(3) 0.0242(18) -0.0029(17) -0.0042(15) -0.0012(18) N9 0.036(3) 0.036(3) 0.053(3) -0.012(2) 0.008(2) 0.002(2) N9' 0.036(3) 0.036(3) 0.053(3) -0.012(2) 0.008(2) 0.002(2) O1 0.0237(15) 0.0356(18) 0.0182(14) 0.0000(13) -0.0033(12) 0.0013(13) O2 0.0253(16) 0.043(2) 0.0447(18) -0.0068(15) -0.0049(14) 0.0024(14) O3 0.023(6) 0.089(12) 0.052(6) -0.002(6) 0.008(5) 0.017(6) O4 0.074(11) 0.094(16) 0.077(8) 0.037(9) 0.004(7) -0.062(12) O5 0.039(7) 0.074(9) 0.032(6) 0.013(6) 0.003(5) -0.014(6) O3' 0.052(6) 0.059(6) 0.092(5) -0.015(4) 0.007(4) 0.028(5) O4' 0.039(4) 0.044(5) 0.069(4) 0.006(4) 0.020(3) -0.001(3) O5' 0.241(17) 0.071(7) 0.191(12) 0.005(7) 0.183(14) -0.034(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 C1 N7 1.318(5) . ? C1 N8 1.363(5) . ? C1 H1 0.9300 . ? C2 N8 1.313(5) . ? C2 N6 1.328(5) . ? C2 H2 0.9300 . ? C3 N6 1.453(5) . ? C3 C4 1.508(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C9 1.370(5) . ? C4 C5 1.379(6) . ? C5 C6 1.378(6) . ? C5 H5 0.9300 . ? C6 C7 1.359(6) . ? C6 H6 0.9300 . ? C7 C8 1.387(6) . ? C7 H7 0.9300 . ? C8 C9 1.399(5) . ? C8 C10 1.431(6) . ? C9 H9 0.9300 . ? C10 N5 1.315(5) . ? C10 O1 1.355(4) . ? C11 N4 1.297(5) . ? C11 O1 1.362(4) . ? C11 C12 1.446(6) . ? C12 C13 1.386(6) . ? C12 C17 1.402(5) . ? C13 C14 1.377(6) . ? C13 H13 0.9300 . ? C14 C15 1.388(6) . ? C14 H14 0.9300 . ? C15 C16 1.384(6) . ? C15 H15 0.9300 . ? C16 C17 1.380(6) . ? C16 C18 1.515(6) . ? C17 H17 0.9300 . ? C18 N3 1.458(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 N1 1.319(5) . ? C19 N3 1.320(5) . ? C19 H19 0.9300 . ? C20 N2 1.297(5) . ? C20 N1 1.360(5) . ? C20 H20 0.9300 . ? Co1 N1 2.121(3) 2_756 ? Co1 N1 2.121(3) . ? Co1 N8 2.129(3) . ? Co1 N8 2.129(3) 2_756 ? Co1 O2 2.133(3) . ? Co1 O2 2.133(3) 2_756 ? N2 N3 1.353(5) . ? N4 N5 1.397(5) . ? N6 N7 1.371(5) . ? N9 O4 1.154(10) . ? N9 O5 1.247(12) . ? N9 O3 1.275(9) . ? O2 H2B 0.8436 . ? O2 H2A 0.8200 . ? 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 C1 N8 114.6(4) . . ? N7 C1 H1 122.7 . . ? N8 C1 H1 122.7 . . ? N8 C2 N6 110.4(4) . . ? N8 C2 H2 124.8 . . ? N6 C2 H2 124.8 . . ? N6 C3 C4 113.0(4) . . ? N6 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? N6 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C9 C4 C5 119.4(4) . . ? C9 C4 C3 123.3(4) . . ? C5 C4 C3 117.3(4) . . ? C6 C5 C4 120.5(4) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C7 C6 C5 120.3(4) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.4(4) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C7 C8 C9 118.9(4) . . ? C7 C8 C10 119.9(3) . . ? C9 C8 C10 121.1(4) . . ? C4 C9 C8 120.4(4) . . ? C4 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? N5 C10 O1 110.9(4) . . ? N5 C10 C8 128.1(4) . . ? O1 C10 C8 121.1(3) . . ? N4 C11 O1 112.2(4) . . ? N4 C11 C12 128.5(4) . . ? O1 C11 C12 119.3(3) . . ? C13 C12 C17 118.9(4) . . ? C13 C12 C11 120.1(4) . . ? C17 C12 C11 121.0(4) . . ? C14 C13 C12 120.1(4) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.6(4) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 120.2(4) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C15 119.2(4) . . ? C17 C16 C18 120.1(4) . . ? C15 C16 C18 120.7(4) . . ? C16 C17 C12 121.0(4) . . ? C16 C17 H17 119.5 . . ? C12 C17 H17 119.5 . . ? N3 C18 C16 112.1(3) . . ? N3 C18 H18A 109.2 . . ? C16 C18 H18A 109.2 . . ? N3 C18 H18B 109.2 . . ? C16 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? N1 C19 N3 110.9(4) . . ? N1 C19 H19 124.6 . . ? N3 C19 H19 124.6 . . ? N2 C20 N1 115.5(4) . . ? N2 C20 H20 122.3 . . ? N1 C20 H20 122.3 . . ? N1 Co1 N1 93.50(18) 2_756 . ? N1 Co1 N8 87.18(13) 2_756 . ? N1 Co1 N8 93.44(13) . . ? N1 Co1 N8 93.44(13) 2_756 2_756 ? N1 Co1 N8 87.18(13) . 2_756 ? N8 Co1 N8 179.1(2) . 2_756 ? N1 Co1 O2 175.65(12) 2_756 . ? N1 Co1 O2 89.01(12) . . ? N8 Co1 O2 89.13(12) . . ? N8 Co1 O2 90.23(12) 2_756 . ? N1 Co1 O2 89.01(12) 2_756 2_756 ? N1 Co1 O2 175.65(12) . 2_756 ? N8 Co1 O2 90.23(12) . 2_756 ? N8 Co1 O2 89.13(12) 2_756 2_756 ? O2 Co1 O2 88.72(16) . 2_756 ? C19 N1 C20 101.6(4) . . ? C19 N1 Co1 136.6(3) . . ? C20 N1 Co1 121.8(3) . . ? C20 N2 N3 102.3(3) . . ? C19 N3 N2 109.7(4) . . ? C19 N3 C18 129.5(4) . . ? N2 N3 C18 120.7(4) . . ? C11 N4 N5 106.1(3) . . ? C10 N5 N4 107.0(3) . . ? C2 N6 N7 110.0(4) . . ? C2 N6 C3 128.9(4) . . ? N7 N6 C3 121.0(4) . . ? C1 N7 N6 101.8(4) . . ? C2 N8 C1 103.1(4) . . ? C2 N8 Co1 130.0(3) . . ? C1 N8 Co1 126.8(3) . . ? O4 N9 O5 122.2(11) . . ? O4 N9 O3 125.4(11) . . ? O5 N9 O3 112.1(9) . . ? C10 O1 C11 103.9(3) . . ? Co1 O2 H2B 114.9 . . ? Co1 O2 H2A 109.5 . . ? H2B O2 H2A 117.9 . . ? 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 N6 C3 C4 C9 -2.7(7) . . . . ? N6 C3 C4 C5 177.9(4) . . . . ? C9 C4 C5 C6 0.5(7) . . . . ? C3 C4 C5 C6 179.9(4) . . . . ? C4 C5 C6 C7 -0.5(8) . . . . ? C5 C6 C7 C8 -0.1(8) . . . . ? C6 C7 C8 C9 0.7(7) . . . . ? C6 C7 C8 C10 -177.8(4) . . . . ? C5 C4 C9 C8 0.1(7) . . . . ? C3 C4 C9 C8 -179.2(4) . . . . ? C7 C8 C9 C4 -0.7(6) . . . . ? C10 C8 C9 C4 177.8(4) . . . . ? C7 C8 C10 N5 -1.4(7) . . . . ? C9 C8 C10 N5 -179.8(4) . . . . ? C7 C8 C10 O1 177.5(4) . . . . ? C9 C8 C10 O1 -1.0(6) . . . . ? N4 C11 C12 C13 0.4(7) . . . . ? O1 C11 C12 C13 179.9(4) . . . . ? N4 C11 C12 C17 -179.9(4) . . . . ? O1 C11 C12 C17 -0.4(6) . . . . ? C17 C12 C13 C14 1.8(7) . . . . ? C11 C12 C13 C14 -178.5(4) . . . . ? C12 C13 C14 C15 -0.5(7) . . . . ? C13 C14 C15 C16 -1.1(7) . . . . ? C14 C15 C16 C17 1.3(7) . . . . ? C14 C15 C16 C18 -176.4(4) . . . . ? C15 C16 C17 C12 0.0(7) . . . . ? C18 C16 C17 C12 177.7(4) . . . . ? C13 C12 C17 C16 -1.6(7) . . . . ? C11 C12 C17 C16 178.7(4) . . . . ? C17 C16 C18 N3 43.6(6) . . . . ? C15 C16 C18 N3 -138.7(4) . . . . ? N3 C19 N1 C20 0.0(4) . . . . ? N3 C19 N1 Co1 -179.0(3) . . . . ? N2 C20 N1 C19 0.0(4) . . . . ? N2 C20 N1 Co1 179.2(3) . . . . ? N1 Co1 N1 C19 -34.0(3) 2_756 . . . ? N8 Co1 N1 C19 53.4(4) . . . . ? N8 Co1 N1 C19 -127.3(4) 2_756 . . . ? O2 Co1 N1 C19 142.4(4) . . . . ? O2 Co1 N1 C19 -159.1(14) 2_756 . . . ? N1 Co1 N1 C20 147.2(3) 2_756 . . . ? N8 Co1 N1 C20 -125.5(3) . . . . ? N8 Co1 N1 C20 53.9(3) 2_756 . . . ? O2 Co1 N1 C20 -36.4(3) . . . . ? O2 Co1 N1 C20 22.1(17) 2_756 . . . ? N1 C20 N2 N3 0.0(4) . . . . ? N1 C19 N3 N2 0.0(4) . . . . ? N1 C19 N3 C18 177.5(4) . . . . ? C20 N2 N3 C19 0.0(4) . . . . ? C20 N2 N3 C18 -177.7(3) . . . . ? C16 C18 N3 C19 -109.5(5) . . . . ? C16 C18 N3 N2 67.8(5) . . . . ? O1 C11 N4 N5 0.1(5) . . . . ? C12 C11 N4 N5 179.6(4) . . . . ? O1 C10 N5 N4 -0.4(5) . . . . ? C8 C10 N5 N4 178.5(4) . . . . ? C11 N4 N5 C10 0.2(5) . . . . ? N8 C2 N6 N7 -0.4(4) . . . . ? N8 C2 N6 C3 175.2(3) . . . . ? C4 C3 N6 C2 -98.4(5) . . . . ? C4 C3 N6 N7 76.8(5) . . . . ? N8 C1 N7 N6 0.6(5) . . . . ? C2 N6 N7 C1 -0.1(4) . . . . ? C3 N6 N7 C1 -176.2(3) . . . . ? N6 C2 N8 C1 0.7(4) . . . . ? N6 C2 N8 Co1 179.8(2) . . . . ? N7 C1 N8 C2 -0.9(5) . . . . ? N7 C1 N8 Co1 -180.0(2) . . . . ? N1 Co1 N8 C2 -141.5(3) 2_756 . . . ? N1 Co1 N8 C2 125.1(3) . . . . ? N8 Co1 N8 C2 -8.2(3) 2_756 . . . ? O2 Co1 N8 C2 36.2(3) . . . . ? O2 Co1 N8 C2 -52.5(3) 2_756 . . . ? N1 Co1 N8 C1 37.3(3) 2_756 . . . ? N1 Co1 N8 C1 -56.0(3) . . . . ? N8 Co1 N8 C1 170.7(3) 2_756 . . . ? O2 Co1 N8 C1 -145.0(3) . . . . ? O2 Co1 N8 C1 126.3(3) 2_756 . . . ? N5 C10 O1 C11 0.4(4) . . . . ? C8 C10 O1 C11 -178.6(4) . . . . ? N4 C11 O1 C10 -0.3(5) . . . . ? C12 C11 O1 C10 -179.9(4) . . . . ? 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 O2 H2B N5 0.84 2.16 2.986(4) 165.9 7_656 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.370 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.068 data_60926cm _database_code_depnum_ccdc_archive 'CCDC 703044' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H40 Cl2 Co N16 O3' _chemical_formula_weight 970.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.215(2) _cell_length_b 10.272(2) _cell_length_c 12.167(3) _cell_angle_alpha 91.563(3) _cell_angle_beta 104.441(3) _cell_angle_gamma 90.913(3) _cell_volume 1114.6(4) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1380 _cell_measurement_theta_min 2.501 _cell_measurement_theta_max 25.445 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 501 _exptl_absorpt_coefficient_mu 0.566 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7929 _exptl_absorpt_correction_T_max 0.9352 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5693 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0643 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3907 _reflns_number_gt 3128 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. the C-C bonds of the half disorder THF were refined in 1.48-1.52\%A distance restraint, and C-O bonds ware refined in 1.36-1.42\%A distance restraint.In total four geometric restraints (DFIX) were used in modeling the disorder. ; _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^)+(0.0514P)^2^+0.4409P] 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 3907 _refine_ls_number_parameters 322 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1186 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.030 _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 Co1 Co 1.0000 1.0000 0.5000 0.01896(18) Uani 1 2 d S . . N1 N 0.5263(3) 1.0283(2) 0.3392(2) 0.0221(6) Uani 1 1 d . . . N2 N 0.5151(3) 0.9115(2) 0.3874(2) 0.0267(6) Uani 1 1 d . . . N3 N 0.7574(3) 0.9834(2) 0.4262(2) 0.0218(6) Uani 1 1 d . . . N4 N 0.4135(3) 0.7275(2) -0.1484(2) 0.0276(6) Uani 1 1 d . . . N5 N 0.5213(3) 0.6295(3) -0.1434(2) 0.0299(7) Uani 1 1 d . . . N6 N 1.0218(3) 0.6232(2) 0.3412(2) 0.0269(6) Uani 1 1 d . . . N7 N 1.1253(3) 0.6845(3) 0.2970(3) 0.0451(9) Uani 1 1 d . . . N8 N 1.0364(3) 0.8235(2) 0.4101(2) 0.0251(6) Uani 1 1 d . . . C1 C 0.6571(4) 0.8901(3) 0.4390(3) 0.0251(7) Uani 1 1 d . . . H1 H 0.6859 0.8163 0.4810 0.030 Uiso 1 1 calc R . . C2 C 0.6697(3) 1.0687(3) 0.3626(3) 0.0217(7) Uani 1 1 d . . . H2 H 0.7033 1.1458 0.3379 0.026 Uiso 1 1 calc R . . C3 C 0.3920(3) 1.0887(3) 0.2711(3) 0.0236(7) Uani 1 1 d . . . H3A H 0.4125 1.1812 0.2675 0.028 Uiso 1 1 calc R . . H3B H 0.3116 1.0789 0.3089 0.028 Uiso 1 1 calc R . . C4 C 0.3392(3) 1.0316(3) 0.1504(3) 0.0213(7) Uani 1 1 d . . . C5 C 0.2174(4) 1.0873(3) 0.0761(3) 0.0291(8) Uani 1 1 d . . . H5 H 0.1688 1.1559 0.1022 0.035 Uiso 1 1 calc R . . C6 C 0.1673(4) 1.0423(3) -0.0361(3) 0.0320(8) Uani 1 1 d . . . H6 H 0.0867 1.0814 -0.0845 0.038 Uiso 1 1 calc R . . C7 C 0.2372(3) 0.9396(3) -0.0757(3) 0.0273(8) Uani 1 1 d . . . H7 H 0.2039 0.9089 -0.1506 0.033 Uiso 1 1 calc R . . C8 C 0.3583(3) 0.8827(3) -0.0022(3) 0.0209(7) Uani 1 1 d . . . C9 C 0.4091(3) 0.9282(3) 0.1104(3) 0.0220(7) Uani 1 1 d . . . H9 H 0.4899 0.8891 0.1587 0.026 Uiso 1 1 calc R . . C10 C 0.4348(3) 0.7752(3) -0.0452(3) 0.0223(7) Uani 1 1 d . . . C11 C 0.5968(4) 0.6270(3) -0.0388(3) 0.0241(7) Uani 1 1 d . . . C12 C 0.7197(4) 0.5417(3) 0.0137(3) 0.0241(7) Uani 1 1 d . . . C13 C 0.7678(4) 0.4457(3) -0.0526(3) 0.0289(8) Uani 1 1 d . . . H13 H 0.7236 0.4366 -0.1300 0.035 Uiso 1 1 calc R . . C14 C 0.8821(4) 0.3644(3) -0.0010(3) 0.0287(8) Uani 1 1 d . . . H14 H 0.9150 0.3006 -0.0443 0.034 Uiso 1 1 calc R . . C15 C 0.9473(4) 0.3776(3) 0.1138(3) 0.0289(8) Uani 1 1 d . . . H15 H 1.0229 0.3216 0.1471 0.035 Uiso 1 1 calc R . . C16 C 0.9022(4) 0.4731(3) 0.1810(3) 0.0249(7) Uani 1 1 d . . . C17 C 0.7880(4) 0.5552(3) 0.1297(3) 0.0268(8) Uani 1 1 d . . . H17 H 0.7568 0.6198 0.1731 0.032 Uiso 1 1 calc R . . C18 C 0.9748(4) 0.4875(3) 0.3071(3) 0.0317(8) Uani 1 1 d . . . H18A H 0.9043 0.4585 0.3492 0.038 Uiso 1 1 calc R . . H18B H 1.0615 0.4324 0.3259 0.038 Uiso 1 1 calc R . . C19 C 0.9719(4) 0.7068(3) 0.4080(3) 0.0261(7) Uani 1 1 d . . . H19 H 0.9013 0.6861 0.4480 0.031 Uiso 1 1 calc R . . C20 C 1.1295(4) 0.8039(3) 0.3419(3) 0.0401(10) Uani 1 1 d . . . H20 H 1.1922 0.8696 0.3274 0.048 Uiso 1 1 calc R . . O2 O 0.6899(7) 0.5557(6) 0.4971(5) 0.0561(16) Uani 0.50 1 d PD . . O1 O 0.5490(2) 0.71567(19) 0.02971(18) 0.0242(5) Uani 1 1 d . . . Cl1 Cl 1.03539(8) 1.13717(7) 0.34592(6) 0.0253(2) Uani 1 1 d . . . C22 C 0.5994(13) 0.4939(17) 0.4049(12) 0.116(6) Uani 0.50 1 d PD . . H22A H 0.6523 0.4353 0.3669 0.139 Uiso 0.50 1 d PR . . H22B H 0.5555 0.5599 0.3534 0.139 Uiso 0.50 1 d PR . . C23 C 0.478(2) 0.4277(17) 0.4412(15) 0.144(10) Uani 0.50 1 d PD . . H23A H 0.4965 0.3360 0.4424 0.173 Uiso 0.50 1 d PR . . H23B H 0.3806 0.4409 0.3915 0.173 Uiso 0.50 1 d PR . . C25 C 0.6124(15) 0.5623(18) 0.5818(11) 0.091(6) Uani 0.50 1 d PD . . H25A H 0.5840 0.6511 0.5887 0.109 Uiso 0.50 1 d PR . . H25B H 0.6798 0.5399 0.6521 0.109 Uiso 0.50 1 d PR . . C24 C 0.476(3) 0.479(3) 0.5587(19) 0.237(16) Uani 0.50 1 d PD . . H24A H 0.4867 0.4096 0.6117 0.284 Uiso 0.50 1 d PR . . H24B H 0.3872 0.5260 0.5603 0.284 Uiso 0.50 1 d PR . . 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 Co1 0.0184(3) 0.0193(3) 0.0187(3) -0.0004(3) 0.0037(3) 0.0021(2) N1 0.0204(14) 0.0227(14) 0.0234(15) 0.0002(12) 0.0061(12) 0.0011(11) N2 0.0261(16) 0.0260(15) 0.0286(16) 0.0054(13) 0.0076(13) -0.0005(12) N3 0.0225(14) 0.0231(14) 0.0200(14) 0.0012(12) 0.0057(12) 0.0024(11) N4 0.0321(16) 0.0240(15) 0.0264(16) 0.0011(13) 0.0065(13) 0.0008(12) N5 0.0346(17) 0.0252(15) 0.0315(17) 0.0000(13) 0.0111(14) 0.0030(12) N6 0.0282(16) 0.0221(14) 0.0301(16) -0.0040(13) 0.0073(13) 0.0029(12) N7 0.044(2) 0.0371(18) 0.063(2) -0.0182(17) 0.0326(18) -0.0095(15) N8 0.0265(15) 0.0224(15) 0.0261(15) -0.0041(12) 0.0065(13) 0.0009(12) C1 0.0300(19) 0.0233(17) 0.0227(17) 0.0045(14) 0.0071(15) 0.0013(14) C2 0.0204(17) 0.0223(17) 0.0222(17) -0.0012(14) 0.0052(14) -0.0003(13) C3 0.0187(17) 0.0238(17) 0.0305(18) 0.0019(15) 0.0097(14) 0.0062(13) C4 0.0170(16) 0.0227(17) 0.0249(17) 0.0021(14) 0.0062(14) 0.0014(13) C5 0.0225(18) 0.0262(18) 0.037(2) 0.0006(16) 0.0040(16) 0.0097(14) C6 0.0244(19) 0.0328(19) 0.035(2) 0.0049(17) -0.0009(16) 0.0090(15) C7 0.0212(18) 0.0315(19) 0.0261(18) 0.0032(15) -0.0002(15) -0.0038(14) C8 0.0183(16) 0.0189(16) 0.0263(17) 0.0043(14) 0.0065(14) 0.0001(12) C9 0.0177(16) 0.0207(16) 0.0268(18) 0.0064(14) 0.0033(14) 0.0027(12) C10 0.0185(16) 0.0220(17) 0.0258(18) 0.0046(14) 0.0041(14) 0.0002(13) C11 0.0266(18) 0.0177(16) 0.0309(19) -0.0035(15) 0.0134(16) -0.0010(13) C12 0.0248(18) 0.0168(16) 0.0338(19) 0.0015(15) 0.0129(15) -0.0012(13) C13 0.0322(19) 0.0267(18) 0.0306(19) -0.0015(16) 0.0138(16) -0.0042(15) C14 0.031(2) 0.0163(16) 0.044(2) -0.0044(16) 0.0201(17) 0.0024(14) C15 0.0269(19) 0.0182(16) 0.045(2) 0.0005(16) 0.0148(17) 0.0033(14) C16 0.0268(18) 0.0139(15) 0.036(2) 0.0039(15) 0.0113(15) 0.0014(13) C17 0.0275(18) 0.0189(16) 0.038(2) -0.0032(15) 0.0165(16) 0.0038(14) C18 0.034(2) 0.0199(17) 0.039(2) -0.0005(16) 0.0052(17) 0.0070(14) C19 0.0319(19) 0.0243(17) 0.0235(18) 0.0032(15) 0.0089(15) 0.0054(14) C20 0.042(2) 0.033(2) 0.052(2) -0.0119(19) 0.025(2) -0.0128(17) O2 0.057(4) 0.070(4) 0.038(3) -0.003(3) 0.007(3) -0.027(3) O1 0.0244(12) 0.0218(11) 0.0275(12) 0.0002(10) 0.0081(10) 0.0048(9) Cl1 0.0243(4) 0.0293(4) 0.0222(4) 0.0059(3) 0.0050(3) 0.0030(3) C22 0.063(8) 0.203(16) 0.077(9) -0.077(10) 0.020(7) -0.016(9) C23 0.24(3) 0.117(15) 0.122(16) -0.076(13) 0.144(18) -0.083(17) C25 0.100(11) 0.121(12) 0.064(8) 0.027(8) 0.039(8) 0.068(11) C24 0.26(3) 0.23(3) 0.27(4) -0.16(3) 0.18(3) -0.14(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N8 2.166(2) 2_776 ? Co1 N8 2.166(2) . ? Co1 N3 2.193(3) 2_776 ? Co1 N3 2.193(3) . ? Co1 Cl1 2.4578(9) 2_776 ? Co1 Cl1 2.4578(9) . ? N1 C2 1.337(4) . ? N1 N2 1.363(3) . ? N1 C3 1.464(4) . ? N2 C1 1.327(4) . ? N3 C2 1.330(4) . ? N3 C1 1.360(4) . ? N4 C10 1.302(4) . ? N4 N5 1.417(4) . ? N5 C11 1.290(4) . ? N6 C19 1.331(4) . ? N6 N7 1.360(4) . ? N6 C18 1.471(4) . ? N7 C20 1.325(4) . ? N8 C19 1.327(4) . ? N8 C20 1.347(4) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.525(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C9 1.389(4) . ? C4 C5 1.395(4) . ? C5 C6 1.391(5) . ? C5 H5 0.9300 . ? C6 C7 1.382(4) . ? C6 H6 0.9300 . ? C7 C8 1.393(4) . ? C7 H7 0.9300 . ? C8 C9 1.397(4) . ? C8 C10 1.473(4) . ? C9 H9 0.9300 . ? C10 O1 1.373(4) . ? C11 O1 1.368(3) . ? C11 C12 1.470(4) . ? C12 C17 1.397(5) . ? C12 C13 1.402(4) . ? C13 C14 1.388(5) . ? C13 H13 0.9300 . ? C14 C15 1.378(5) . ? C14 H14 0.9300 . ? C15 C16 1.394(4) . ? C15 H15 0.9300 . ? C16 C17 1.392(4) . ? C16 C18 1.515(5) . ? C17 H17 0.9300 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? O2 C22 1.355(13) . ? O2 C25 1.393(9) . ? C22 C23 1.469(10) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C23 C24 1.513(9) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C25 C24 1.478(10) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? 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 Co1 N8 180.0 2_776 . ? N8 Co1 N3 91.28(9) 2_776 2_776 ? N8 Co1 N3 88.72(9) . 2_776 ? N8 Co1 N3 88.72(9) 2_776 . ? N8 Co1 N3 91.28(9) . . ? N3 Co1 N3 180.00 2_776 . ? N8 Co1 Cl1 92.11(7) 2_776 2_776 ? N8 Co1 Cl1 87.89(7) . 2_776 ? N3 Co1 Cl1 91.94(7) 2_776 2_776 ? N3 Co1 Cl1 88.06(7) . 2_776 ? N8 Co1 Cl1 87.89(7) 2_776 . ? N8 Co1 Cl1 92.11(7) . . ? N3 Co1 Cl1 88.06(7) 2_776 . ? N3 Co1 Cl1 91.94(7) . . ? Cl1 Co1 Cl1 180.00 2_776 . ? C2 N1 N2 110.0(2) . . ? C2 N1 C3 129.7(3) . . ? N2 N1 C3 120.2(2) . . ? C1 N2 N1 101.8(2) . . ? C2 N3 C1 102.2(3) . . ? C2 N3 Co1 127.8(2) . . ? C1 N3 Co1 129.9(2) . . ? C10 N4 N5 105.9(3) . . ? C11 N5 N4 106.4(3) . . ? C19 N6 N7 109.4(3) . . ? C19 N6 C18 130.1(3) . . ? N7 N6 C18 120.5(3) . . ? C20 N7 N6 102.2(3) . . ? C19 N8 C20 102.2(3) . . ? C19 N8 Co1 128.6(2) . . ? C20 N8 Co1 129.2(2) . . ? N2 C1 N3 115.4(3) . . ? N2 C1 H1 122.3 . . ? N3 C1 H1 122.3 . . ? N3 C2 N1 110.5(3) . . ? N3 C2 H2 124.7 . . ? N1 C2 H2 124.7 . . ? N1 C3 C4 114.0(2) . . ? N1 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? N1 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C9 C4 C5 118.6(3) . . ? C9 C4 C3 122.8(3) . . ? C5 C4 C3 118.6(3) . . ? C6 C5 C4 121.2(3) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C7 C6 C5 120.1(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 119.1(3) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C7 C8 C9 120.8(3) . . ? C7 C8 C10 119.1(3) . . ? C9 C8 C10 120.1(3) . . ? C4 C9 C8 120.2(3) . . ? C4 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? N4 C10 O1 112.4(3) . . ? N4 C10 C8 129.2(3) . . ? O1 C10 C8 118.4(3) . . ? N5 C11 O1 112.8(3) . . ? N5 C11 C12 129.0(3) . . ? O1 C11 C12 118.1(3) . . ? C17 C12 C13 119.9(3) . . ? C17 C12 C11 120.1(3) . . ? C13 C12 C11 120.0(3) . . ? C14 C13 C12 119.2(3) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C15 C14 C13 120.5(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 121.3(3) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C17 C16 C15 118.4(3) . . ? C17 C16 C18 120.5(3) . . ? C15 C16 C18 121.1(3) . . ? C16 C17 C12 120.7(3) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? N6 C18 C16 111.6(3) . . ? N6 C18 H18A 109.3 . . ? C16 C18 H18A 109.3 . . ? N6 C18 H18B 109.3 . . ? C16 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? N8 C19 N6 111.0(3) . . ? N8 C19 H19 124.5 . . ? N6 C19 H19 124.5 . . ? N7 C20 N8 115.3(3) . . ? N7 C20 H20 122.4 . . ? N8 C20 H20 122.4 . . ? C22 O2 C25 107.8(9) . . ? C22 O2 C24 37.7(7) . 2_666 ? C25 O2 C24 72.5(9) . 2_666 ? C22 O2 C23 88.5(7) . 2_666 ? C25 O2 C23 23.2(10) . 2_666 ? C24 O2 C23 51.3(5) 2_666 2_666 ? C11 O1 C10 102.5(2) . . ? C24 C22 O2 81.6(15) 2_666 . ? C24 C22 C23 45.4(18) 2_666 . ? O2 C22 C23 108.0(12) . . ? C24 C22 H22A 157.6 2_666 . ? O2 C22 H22A 112.9 . . ? C23 C22 H22A 112.2 . . ? C24 C22 H22B 81.3 2_666 . ? O2 C22 H22B 107.0 . . ? C23 C22 H22B 107.6 . . ? H22A C22 H22B 108.8 . . ? C25 C23 C24 104(3) 2_666 2_666 ? C25 C23 C22 128(3) 2_666 . ? C24 C23 C22 40.2(12) 2_666 . ? C25 C23 C24 91(2) 2_666 . ? C24 C23 C24 79(2) 2_666 . ? C22 C23 C24 109.2(14) . . ? C25 C23 O2 42.2(11) 2_666 2_666 ? C24 C23 O2 107.0(16) 2_666 2_666 ? C22 C23 O2 147.2(13) . 2_666 ? C24 C23 O2 52.4(9) . 2_666 ? C25 C23 C23 98(2) 2_666 2_666 ? C24 C23 C23 48.0(13) 2_666 2_666 ? C22 C23 C23 81.2(10) . 2_666 ? C24 C23 C23 31.0(11) . 2_666 ? O2 C23 C23 72.1(8) 2_666 2_666 ? C25 C23 H23A 108.6 2_666 . ? C24 C23 H23A 145.5 2_666 . ? C22 C23 H23A 107.8 . . ? C24 C23 H23A 110.3 . . ? O2 C23 H23A 104.4 2_666 . ? C23 C23 H23A 134.0 2_666 . ? C25 C23 H23B 18.4 2_666 . ? C24 C23 H23B 99.2 2_666 . ? C22 C23 H23B 113.1 . . ? C24 C23 H23B 108.1 . . ? O2 C23 H23B 60.6 2_666 . ? C23 C23 H23B 108.6 2_666 . ? H23A C23 H23B 108.5 . . ? C23 C25 O2 114.6(18) 2_666 . ? C23 C25 C24 44(2) 2_666 . ? O2 C25 C24 114.2(12) . . ? C23 C25 C24 60.6(18) 2_666 2_666 ? O2 C25 C24 57.6(6) . 2_666 ? C24 C25 C24 62.0(16) . 2_666 ? C23 C25 H25A 67.1 2_666 . ? O2 C25 H25A 107.5 . . ? C24 C25 H25A 108.4 . . ? C24 C25 H25A 102.3 2_666 . ? C23 C25 H25B 136.4 2_666 . ? O2 C25 H25B 108.1 . . ? C24 C25 H25B 110.2 . . ? C24 C25 H25B 149.2 2_666 . ? H25A C25 H25B 108.3 . . ? C22 C24 C23 94(3) 2_666 2_666 ? C22 C24 C25 115.4(16) 2_666 . ? C23 C24 C25 32.3(16) 2_666 . ? C22 C24 C23 136(3) 2_666 . ? C23 C24 C23 101(2) 2_666 . ? C25 C24 C23 98.5(13) . . ? C22 C24 O2 60.7(15) 2_666 2_666 ? C23 C24 O2 123(3) 2_666 2_666 ? C25 C24 O2 154(3) . 2_666 ? C23 C24 O2 76.3(11) . 2_666 ? C22 C24 C24 134(5) 2_666 2_666 ? C23 C24 C24 63(2) 2_666 2_666 ? C25 C24 C24 66.6(13) . 2_666 ? C23 C24 C24 38.1(9) . 2_666 ? O2 C24 C24 97(2) 2_666 2_666 ? C22 C24 C25 108(2) 2_666 2_666 ? C23 C24 C25 106(3) 2_666 2_666 ? C25 C24 C25 118.0(16) . 2_666 ? C23 C24 C25 28.0(9) . 2_666 ? O2 C24 C25 49.9(8) 2_666 2_666 ? C24 C24 C25 51.4(10) 2_666 2_666 ? C22 C24 H24A 83.2 2_666 . ? C23 C24 H24A 135.7 2_666 . ? C25 C24 H24A 110.9 . . ? C23 C24 H24A 111.5 . . ? O2 C24 H24A 94.2 2_666 . ? C24 C24 H24A 141.4 2_666 . ? C25 C24 H24A 116.7 2_666 . ? C22 C24 H24B 28.1 2_666 . ? C23 C24 H24B 82.9 2_666 . ? C25 C24 H24B 112.9 . . ? C23 C24 H24B 113.4 . . ? O2 C24 H24B 50.3 2_666 . ? C24 C24 H24B 106.3 2_666 . ? C25 C24 H24B 86.5 2_666 . ? H24A C24 H24B 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 C2 N1 N2 C1 0.7(3) . . . . ? C3 N1 N2 C1 179.2(3) . . . . ? N8 Co1 N3 C2 59.0(3) 2_776 . . . ? N8 Co1 N3 C2 -121.0(3) . . . . ? N3 Co1 N3 C2 -74(100) 2_776 . . . ? Cl1 Co1 N3 C2 151.2(2) 2_776 . . . ? Cl1 Co1 N3 C2 -28.8(2) . . . . ? N8 Co1 N3 C1 -116.0(3) 2_776 . . . ? N8 Co1 N3 C1 64.0(3) . . . . ? N3 Co1 N3 C1 111(100) 2_776 . . . ? Cl1 Co1 N3 C1 -23.9(3) 2_776 . . . ? Cl1 Co1 N3 C1 156.1(3) . . . . ? C10 N4 N5 C11 0.0(3) . . . . ? C19 N6 N7 C20 -0.2(4) . . . . ? C18 N6 N7 C20 176.2(3) . . . . ? N8 Co1 N8 C19 -107(100) 2_776 . . . ? N3 Co1 N8 C19 127.2(3) 2_776 . . . ? N3 Co1 N8 C19 -52.8(3) . . . . ? Cl1 Co1 N8 C19 35.3(3) 2_776 . . . ? Cl1 Co1 N8 C19 -144.7(3) . . . . ? N8 Co1 N8 C20 73(100) 2_776 . . . ? N3 Co1 N8 C20 -52.9(3) 2_776 . . . ? N3 Co1 N8 C20 127.1(3) . . . . ? Cl1 Co1 N8 C20 -144.9(3) 2_776 . . . ? Cl1 Co1 N8 C20 35.1(3) . . . . ? N1 N2 C1 N3 -0.7(3) . . . . ? C2 N3 C1 N2 0.5(3) . . . . ? Co1 N3 C1 N2 176.5(2) . . . . ? C1 N3 C2 N1 0.0(3) . . . . ? Co1 N3 C2 N1 -176.16(19) . . . . ? N2 N1 C2 N3 -0.4(3) . . . . ? C3 N1 C2 N3 -178.8(3) . . . . ? C2 N1 C3 C4 98.9(4) . . . . ? N2 N1 C3 C4 -79.4(3) . . . . ? N1 C3 C4 C9 2.3(4) . . . . ? N1 C3 C4 C5 -176.3(3) . . . . ? C9 C4 C5 C6 -0.9(5) . . . . ? C3 C4 C5 C6 177.8(3) . . . . ? C4 C5 C6 C7 0.7(5) . . . . ? C5 C6 C7 C8 -0.3(5) . . . . ? C6 C7 C8 C9 0.0(5) . . . . ? C6 C7 C8 C10 -178.6(3) . . . . ? C5 C4 C9 C8 0.6(4) . . . . ? C3 C4 C9 C8 -178.0(3) . . . . ? C7 C8 C9 C4 -0.2(5) . . . . ? C10 C8 C9 C4 178.5(3) . . . . ? N5 N4 C10 O1 -0.4(3) . . . . ? N5 N4 C10 C8 177.5(3) . . . . ? C7 C8 C10 N4 5.5(5) . . . . ? C9 C8 C10 N4 -173.2(3) . . . . ? C7 C8 C10 O1 -176.7(3) . . . . ? C9 C8 C10 O1 4.6(4) . . . . ? N4 N5 C11 O1 0.4(4) . . . . ? N4 N5 C11 C12 178.5(3) . . . . ? N5 C11 C12 C17 179.7(3) . . . . ? O1 C11 C12 C17 -2.2(4) . . . . ? N5 C11 C12 C13 -0.8(5) . . . . ? O1 C11 C12 C13 177.3(3) . . . . ? C17 C12 C13 C14 0.7(5) . . . . ? C11 C12 C13 C14 -178.8(3) . . . . ? C12 C13 C14 C15 0.2(5) . . . . ? C13 C14 C15 C16 -0.8(5) . . . . ? C14 C15 C16 C17 0.6(5) . . . . ? C14 C15 C16 C18 -179.7(3) . . . . ? C15 C16 C17 C12 0.3(5) . . . . ? C18 C16 C17 C12 -179.4(3) . . . . ? C13 C12 C17 C16 -1.0(5) . . . . ? C11 C12 C17 C16 178.5(3) . . . . ? C19 N6 C18 C16 113.9(4) . . . . ? N7 N6 C18 C16 -61.5(4) . . . . ? C17 C16 C18 N6 -50.1(4) . . . . ? C15 C16 C18 N6 130.2(3) . . . . ? C20 N8 C19 N6 -1.0(4) . . . . ? Co1 N8 C19 N6 178.9(2) . . . . ? N7 N6 C19 N8 0.8(4) . . . . ? C18 N6 C19 N8 -175.1(3) . . . . ? N6 N7 C20 N8 -0.5(5) . . . . ? C19 N8 C20 N7 0.9(4) . . . . ? Co1 N8 C20 N7 -179.0(3) . . . . ? N5 C11 O1 C10 -0.6(3) . . . . ? C12 C11 O1 C10 -179.0(3) . . . . ? N4 C10 O1 C11 0.6(3) . . . . ? C8 C10 O1 C11 -177.5(3) . . . . ? C25 O2 C22 C24 22(3) . . . 2_666 ? C23 O2 C22 C24 9(2) 2_666 . . 2_666 ? C25 O2 C22 C23 -15.8(16) . . . . ? C24 O2 C22 C23 -37(2) 2_666 . . . ? C23 O2 C22 C23 -28.9(18) 2_666 . . . ? C24 C22 C23 C25 64(3) 2_666 . . 2_666 ? O2 C22 C23 C25 121(3) . . . 2_666 ? O2 C22 C23 C24 58(3) . . . 2_666 ? C24 C22 C23 C24 -44(4) 2_666 . . . ? O2 C22 C23 C24 14(2) . . . . ? C24 C22 C23 O2 5(3) 2_666 . . 2_666 ? O2 C22 C23 O2 63(3) . . . 2_666 ? C24 C22 C23 C23 -30(3) 2_666 . . 2_666 ? O2 C22 C23 C23 27.4(18) . . . 2_666 ? C22 O2 C25 C23 -35(3) . . . 2_666 ? C24 O2 C25 C23 -21(3) 2_666 . . 2_666 ? C22 O2 C25 C24 13(2) . . . . ? C24 O2 C25 C24 27(3) 2_666 . . . ? C23 O2 C25 C24 48(3) 2_666 . . . ? C22 O2 C25 C24 -13.7(18) . . . 2_666 ? C23 O2 C25 C24 21(3) 2_666 . . 2_666 ? C23 C25 C24 C22 -54(3) 2_666 . . 2_666 ? O2 C25 C24 C22 -155(3) . . . 2_666 ? C24 C25 C24 C22 -129(5) 2_666 . . 2_666 ? O2 C25 C24 C23 -101(2) . . . 2_666 ? C24 C25 C24 C23 -76(3) 2_666 . . 2_666 ? C23 C25 C24 C23 97(3) 2_666 . . . ? O2 C25 C24 C23 -4(3) . . . . ? C24 C25 C24 C23 21.3(11) 2_666 . . . ? C23 C25 C24 O2 21(3) 2_666 . . 2_666 ? O2 C25 C24 O2 -80(3) . . . 2_666 ? C24 C25 C24 O2 -55(3) 2_666 . . 2_666 ? C23 C25 C24 C24 76(3) 2_666 . . 2_666 ? O2 C25 C24 C24 -25(2) . . . 2_666 ? C23 C25 C24 C25 76(3) 2_666 . . 2_666 ? O2 C25 C24 C25 -25(2) . . . 2_666 ? C24 C25 C24 C25 0.000(2) 2_666 . . 2_666 ? C25 C23 C24 C22 4(4) 2_666 . . 2_666 ? C24 C23 C24 C22 108(6) 2_666 . . 2_666 ? C22 C23 C24 C22 135(4) . . . 2_666 ? O2 C23 C24 C22 -14(3) 2_666 . . 2_666 ? C23 C23 C24 C22 108(6) 2_666 . . 2_666 ? C25 C23 C24 C23 -104(3) 2_666 . . 2_666 ? C24 C23 C24 C23 0.000(2) 2_666 . . 2_666 ? C22 C23 C24 C23 27(3) . . . 2_666 ? O2 C23 C24 C23 -122(3) 2_666 . . 2_666 ? C25 C23 C24 C25 -137(2) 2_666 . . . ? C24 C23 C24 C25 -32.7(16) 2_666 . . . ? C22 C23 C24 C25 -6(3) . . . . ? O2 C23 C24 C25 -154(3) 2_666 . . . ? C23 C23 C24 C25 -32.7(16) 2_666 . . . ? C25 C23 C24 O2 18(2) 2_666 . . 2_666 ? C24 C23 C24 O2 122(3) 2_666 . . 2_666 ? C22 C23 C24 O2 148.8(19) . . . 2_666 ? C23 C23 C24 O2 122(3) 2_666 . . 2_666 ? C25 C23 C24 C24 -104(3) 2_666 . . 2_666 ? C22 C23 C24 C24 27(3) . . . 2_666 ? O2 C23 C24 C24 -122(3) 2_666 . . 2_666 ? C23 C23 C24 C24 0.000(11) 2_666 . . 2_666 ? C24 C23 C24 C25 104(3) 2_666 . . 2_666 ? C22 C23 C24 C25 131(3) . . . 2_666 ? O2 C23 C24 C25 -18(2) 2_666 . . 2_666 ? C23 C23 C24 C25 104(3) 2_666 . . 2_666 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.503 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.070 data_60926bm _database_code_depnum_ccdc_archive 'CCDC 703045' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H40 Cl2 Mn N16 O3' _chemical_formula_weight 966.76 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' O O 0.0106 0.0060 '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' 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 9.215(2) _cell_length_b 10.272(2) _cell_length_c 12.167(3) _cell_angle_alpha 91.563(3) _cell_angle_beta 104.441(3) _cell_angle_gamma 90.913(3) _cell_volume 1114.6(4) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1577 _cell_measurement_theta_min 2.283 _cell_measurement_theta_max 26.407 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 499 _exptl_absorpt_coefficient_mu 0.477 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7827 _exptl_absorpt_correction_T_max 0.9106 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5429 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3888 _reflns_number_gt 3175 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. the C-C bonds of the half disorder THF were refined in 1.48-1.52\%A distance restraint, and C-O bonds ware refined in 1.36-1.42\%A distance restraint.In total four geometric restraints (DFIX) were used in modeling the disorder. ; _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^)+(0.0510P)^2^+0.4312P] 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 3888 _refine_ls_number_parameters 322 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1138 _refine_ls_wR_factor_gt 0.1057 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.039 _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 Mn1 Mn 1.0000 1.0000 0.5000 0.01997(17) Uani 1 2 d S . . N1 N 0.5182(2) 1.0262(2) 0.33666(19) 0.0225(5) Uani 1 1 d . . . N2 N 0.5077(3) 0.9104(2) 0.3863(2) 0.0263(6) Uani 1 1 d . . . N3 N 0.7471(2) 0.9824(2) 0.42322(19) 0.0238(5) Uani 1 1 d . . . N4 N 0.4159(3) 0.7294(2) -0.1481(2) 0.0281(6) Uani 1 1 d . . . N5 N 0.5226(3) 0.6318(2) -0.1432(2) 0.0297(6) Uani 1 1 d . . . N6 N 1.0197(3) 0.6148(2) 0.3395(2) 0.0276(6) Uani 1 1 d . . . N7 N 1.1273(3) 0.6718(3) 0.2978(3) 0.0486(8) Uani 1 1 d . . . N8 N 1.0396(3) 0.8139(2) 0.4079(2) 0.0278(6) Uani 1 1 d . . . C1 C 0.6483(3) 0.8891(3) 0.4375(2) 0.0256(6) Uani 1 1 d . . . H1 H 0.6776 0.8159 0.4800 0.031 Uiso 1 1 calc R . . C2 C 0.6607(3) 1.0671(3) 0.3594(2) 0.0248(6) Uani 1 1 d . . . H2 H 0.6943 1.1439 0.3342 0.030 Uiso 1 1 calc R . . C3 C 0.3854(3) 1.0858(3) 0.2677(2) 0.0260(7) Uani 1 1 d . . . H3A H 0.4053 1.1784 0.2647 0.031 Uiso 1 1 calc R . . H3B H 0.3038 1.0751 0.3042 0.031 Uiso 1 1 calc R . . C4 C 0.3362(3) 1.0296(3) 0.1481(2) 0.0236(6) Uani 1 1 d . . . C5 C 0.2150(3) 1.0848(3) 0.0736(3) 0.0306(7) Uani 1 1 d . . . H5 H 0.1655 1.1531 0.0992 0.037 Uiso 1 1 calc R . . C6 C 0.1670(3) 1.0398(3) -0.0381(3) 0.0328(7) Uani 1 1 d . . . H6 H 0.0862 1.0784 -0.0868 0.039 Uiso 1 1 calc R . . C7 C 0.2380(3) 0.9383(3) -0.0774(3) 0.0272(7) Uani 1 1 d . . . H7 H 0.2057 0.9080 -0.1524 0.033 Uiso 1 1 calc R . . C8 C 0.3584(3) 0.8815(3) -0.0035(2) 0.0223(6) Uani 1 1 d . . . C9 C 0.4068(3) 0.9265(3) 0.1088(2) 0.0228(6) Uani 1 1 d . . . H9 H 0.4869 0.8872 0.1577 0.027 Uiso 1 1 calc R . . C10 C 0.4355(3) 0.7759(3) -0.0453(2) 0.0223(6) Uani 1 1 d . . . C11 C 0.5969(3) 0.6273(3) -0.0388(2) 0.0248(6) Uani 1 1 d . . . C12 C 0.7179(3) 0.5420(3) 0.0131(2) 0.0241(6) Uani 1 1 d . . . C13 C 0.7664(3) 0.4479(3) -0.0538(3) 0.0271(7) Uani 1 1 d . . . H13 H 0.7231 0.4404 -0.1315 0.032 Uiso 1 1 calc R . . C14 C 0.8791(3) 0.3664(3) -0.0036(3) 0.0299(7) Uani 1 1 d . . . H14 H 0.9122 0.3038 -0.0477 0.036 Uiso 1 1 calc R . . C15 C 0.9432(3) 0.3765(3) 0.1111(3) 0.0279(7) Uani 1 1 d . . . H15 H 1.0183 0.3197 0.1437 0.033 Uiso 1 1 calc R . . C16 C 0.8977(3) 0.4703(3) 0.1794(3) 0.0254(6) Uani 1 1 d . . . C17 C 0.7842(3) 0.5529(3) 0.1288(3) 0.0252(6) Uani 1 1 d . . . H17 H 0.7522 0.6163 0.1729 0.030 Uiso 1 1 calc R . . C18 C 0.9680(4) 0.4812(3) 0.3048(3) 0.0324(7) Uani 1 1 d . . . H18A H 0.8954 0.4545 0.3458 0.039 Uiso 1 1 calc R . . H18B H 1.0522 0.4234 0.3238 0.039 Uiso 1 1 calc R . . C19 C 0.9702(3) 0.6998(3) 0.4041(2) 0.0273(7) Uani 1 1 d . . . H19 H 0.8963 0.6818 0.4418 0.033 Uiso 1 1 calc R . . C20 C 1.1338(4) 0.7911(3) 0.3416(3) 0.0434(9) Uani 1 1 d . . . H20 H 1.1990 0.8550 0.3276 0.052 Uiso 1 1 calc R . . O2 O 0.6852(6) 0.5585(5) 0.4955(4) 0.0578(14) Uani 0.50 1 d PD . . O1 O 0.5482(2) 0.71559(17) 0.02942(16) 0.0241(4) Uani 1 1 d . . . Cl1 Cl 1.03709(7) 1.13985(7) 0.34253(6) 0.02581(19) Uani 1 1 d . . . C22 C 0.5917(13) 0.5034(15) 0.4007(10) 0.107(5) Uani 0.50 1 d PD . . H22A H 0.6447 0.4448 0.3626 0.129 Uiso 0.50 1 d PR . . H22B H 0.5478 0.5694 0.3492 0.129 Uiso 0.50 1 d PR . . C23 C 0.478(2) 0.4334(19) 0.4428(12) 0.139(9) Uani 0.50 1 d PD . . H23A H 0.4970 0.3417 0.4439 0.166 Uiso 0.50 1 d PR . . H23B H 0.3811 0.4466 0.3931 0.166 Uiso 0.50 1 d PR . . C25 C 0.6105(11) 0.5710(11) 0.5811(8) 0.062(3) Uani 0.50 1 d PD . . H25A H 0.5821 0.6598 0.5880 0.075 Uiso 0.50 1 d PR . . H25B H 0.6779 0.5485 0.6514 0.075 Uiso 0.50 1 d PR . . C24 C 0.478(2) 0.483(2) 0.5601(15) 0.200(12) Uani 0.50 1 d PD . . H24A H 0.4892 0.4139 0.6131 0.240 Uiso 0.50 1 d PR . . H24B H 0.3897 0.5304 0.5617 0.240 Uiso 0.50 1 d PR . . 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 Mn1 0.0195(3) 0.0197(3) 0.0195(3) -0.0020(2) 0.0030(2) 0.0011(2) N1 0.0216(12) 0.0249(13) 0.0213(13) -0.0010(10) 0.0060(10) 0.0001(10) N2 0.0239(13) 0.0280(13) 0.0266(14) 0.0026(11) 0.0053(11) -0.0023(10) N3 0.0221(13) 0.0264(13) 0.0221(13) 0.0011(10) 0.0040(10) 0.0013(10) N4 0.0308(14) 0.0257(13) 0.0267(15) 0.0005(11) 0.0050(11) 0.0011(11) N5 0.0343(15) 0.0266(13) 0.0284(15) -0.0036(11) 0.0090(12) 0.0034(11) N6 0.0290(14) 0.0230(13) 0.0287(14) -0.0040(11) 0.0038(11) 0.0018(11) N7 0.0441(18) 0.0432(17) 0.065(2) -0.0240(16) 0.0292(16) -0.0125(14) N8 0.0280(14) 0.0243(13) 0.0309(15) -0.0030(11) 0.0078(11) -0.0011(11) C1 0.0275(16) 0.0244(15) 0.0242(16) 0.0031(12) 0.0047(13) 0.0000(12) C2 0.0233(15) 0.0240(15) 0.0278(16) -0.0007(13) 0.0076(13) -0.0001(12) C3 0.0205(15) 0.0281(16) 0.0306(17) -0.0010(13) 0.0083(13) 0.0058(12) C4 0.0189(14) 0.0229(15) 0.0291(17) 0.0005(12) 0.0063(12) -0.0009(11) C5 0.0248(16) 0.0302(17) 0.0352(18) -0.0032(14) 0.0045(14) 0.0087(13) C6 0.0227(16) 0.0370(18) 0.0337(19) 0.0058(14) -0.0034(14) 0.0091(13) C7 0.0243(16) 0.0308(16) 0.0235(16) -0.0005(13) 0.0011(13) -0.0028(13) C8 0.0191(14) 0.0209(14) 0.0266(16) 0.0002(12) 0.0054(12) -0.0030(11) C9 0.0177(14) 0.0245(15) 0.0249(16) 0.0040(12) 0.0023(12) 0.0016(11) C10 0.0207(14) 0.0226(15) 0.0226(16) 0.0037(12) 0.0035(12) -0.0012(11) C11 0.0280(16) 0.0224(15) 0.0251(17) -0.0052(12) 0.0094(13) -0.0035(12) C12 0.0236(15) 0.0197(14) 0.0305(17) -0.0022(12) 0.0105(13) -0.0034(11) C13 0.0295(16) 0.0243(15) 0.0283(17) -0.0043(13) 0.0098(13) -0.0045(12) C14 0.0337(17) 0.0217(15) 0.0379(19) -0.0076(13) 0.0168(15) 0.0015(13) C15 0.0255(16) 0.0148(14) 0.045(2) -0.0010(13) 0.0115(14) 0.0011(12) C16 0.0255(15) 0.0179(14) 0.0328(17) -0.0013(12) 0.0075(13) -0.0019(12) C17 0.0272(16) 0.0179(14) 0.0322(17) -0.0045(12) 0.0114(13) -0.0001(12) C18 0.0411(19) 0.0193(15) 0.0347(18) 0.0001(13) 0.0053(15) 0.0050(13) C19 0.0305(16) 0.0255(16) 0.0272(17) -0.0025(13) 0.0095(13) 0.0043(13) C20 0.042(2) 0.0366(19) 0.056(2) -0.0213(17) 0.0227(18) -0.0142(16) O2 0.060(3) 0.071(4) 0.039(3) -0.001(3) 0.009(3) -0.026(3) O1 0.0234(10) 0.0234(10) 0.0244(11) -0.0011(8) 0.0038(9) 0.0036(8) Cl1 0.0250(4) 0.0297(4) 0.0221(4) 0.0059(3) 0.0040(3) 0.0029(3) C22 0.084(8) 0.174(13) 0.063(7) -0.050(8) 0.025(6) -0.058(9) C23 0.148(15) 0.182(16) 0.111(12) -0.085(11) 0.097(12) -0.129(14) C25 0.079(8) 0.057(6) 0.058(6) -0.002(5) 0.029(6) 0.003(6) C24 0.178(19) 0.27(3) 0.18(2) -0.113(19) 0.120(15) -0.162(19) _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 Mn1 N8 2.270(2) . ? Mn1 N8 2.270(2) 2_776 ? Mn1 N3 2.286(2) 2_776 ? Mn1 N3 2.286(2) . ? Mn1 Cl1 2.5125(8) . ? Mn1 Cl1 2.5125(8) 2_776 ? N1 C2 1.331(3) . ? N1 N2 1.362(3) . ? N1 C3 1.455(3) . ? N2 C1 1.315(4) . ? N3 C2 1.321(3) . ? N3 C1 1.356(3) . ? N4 C10 1.295(4) . ? N4 N5 1.408(3) . ? N5 C11 1.287(4) . ? N6 C19 1.320(3) . ? N6 N7 1.354(3) . ? N6 C18 1.461(3) . ? N7 C20 1.317(4) . ? N8 C19 1.321(4) . ? N8 C20 1.344(4) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.508(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C9 1.387(4) . ? C4 C5 1.392(4) . ? C5 C6 1.383(4) . ? C5 H5 0.9300 . ? C6 C7 1.377(4) . ? C6 H6 0.9300 . ? C7 C8 1.390(4) . ? C7 H7 0.9300 . ? C8 C9 1.391(4) . ? C8 C10 1.454(4) . ? C9 H9 0.9300 . ? C10 O1 1.368(3) . ? C11 O1 1.368(3) . ? C11 C12 1.455(4) . ? C12 C17 1.388(4) . ? C12 C13 1.397(4) . ? C13 C14 1.375(4) . ? C13 H13 0.9300 . ? C14 C15 1.373(4) . ? C14 H14 0.9300 . ? C15 C16 1.392(4) . ? C15 H15 0.9300 . ? C16 C17 1.389(4) . ? C16 C18 1.502(4) . ? C17 H17 0.9300 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? O2 C22 1.359(11) . ? O2 C25 1.389(8) . ? C22 C23 1.463(9) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C23 C24 1.502(9) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C25 C24 1.473(9) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? 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 Mn1 N8 180.00 . 2_776 ? N8 Mn1 N3 88.36(8) . 2_776 ? N8 Mn1 N3 91.64(8) 2_776 2_776 ? N8 Mn1 N3 91.64(8) . . ? N8 Mn1 N3 88.36(8) 2_776 . ? N3 Mn1 N3 180.0 2_776 . ? N8 Mn1 Cl1 92.58(7) . . ? N8 Mn1 Cl1 87.42(7) 2_776 . ? N3 Mn1 Cl1 87.82(6) 2_776 . ? N3 Mn1 Cl1 92.18(6) . . ? N8 Mn1 Cl1 87.42(7) . 2_776 ? N8 Mn1 Cl1 92.58(7) 2_776 2_776 ? N3 Mn1 Cl1 92.18(6) 2_776 2_776 ? N3 Mn1 Cl1 87.82(6) . 2_776 ? Cl1 Mn1 Cl1 180.00 . 2_776 ? C2 N1 N2 110.1(2) . . ? C2 N1 C3 129.2(2) . . ? N2 N1 C3 120.7(2) . . ? C1 N2 N1 102.2(2) . . ? C2 N3 C1 103.2(2) . . ? C2 N3 Mn1 127.45(19) . . ? C1 N3 Mn1 129.22(19) . . ? C10 N4 N5 106.2(2) . . ? C11 N5 N4 106.7(2) . . ? C19 N6 N7 109.7(2) . . ? C19 N6 C18 129.7(3) . . ? N7 N6 C18 120.5(2) . . ? C20 N7 N6 102.1(2) . . ? C19 N8 C20 102.2(2) . . ? C19 N8 Mn1 127.7(2) . . ? C20 N8 Mn1 130.1(2) . . ? N2 C1 N3 114.6(3) . . ? N2 C1 H1 122.7 . . ? N3 C1 H1 122.7 . . ? N3 C2 N1 109.8(2) . . ? N3 C2 H2 125.1 . . ? N1 C2 H2 125.1 . . ? N1 C3 C4 113.8(2) . . ? N1 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? N1 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C9 C4 C5 118.6(3) . . ? C9 C4 C3 123.2(3) . . ? C5 C4 C3 118.2(2) . . ? C6 C5 C4 121.0(3) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C7 C6 C5 120.4(3) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 119.2(3) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C7 C8 C9 120.5(3) . . ? C7 C8 C10 119.3(3) . . ? C9 C8 C10 120.2(2) . . ? C4 C9 C8 120.3(3) . . ? C4 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? N4 C10 O1 112.1(2) . . ? N4 C10 C8 129.0(3) . . ? O1 C10 C8 118.9(2) . . ? N5 C11 O1 112.2(2) . . ? N5 C11 C12 129.3(3) . . ? O1 C11 C12 118.5(2) . . ? C17 C12 C13 119.9(3) . . ? C17 C12 C11 120.4(2) . . ? C13 C12 C11 119.7(3) . . ? C14 C13 C12 119.2(3) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C15 C14 C13 120.7(3) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 121.1(3) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 118.3(3) . . ? C17 C16 C18 120.7(3) . . ? C15 C16 C18 121.0(3) . . ? C12 C17 C16 120.8(3) . . ? C12 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? N6 C18 C16 110.9(2) . . ? N6 C18 H18A 109.5 . . ? C16 C18 H18A 109.5 . . ? N6 C18 H18B 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 108.0 . . ? N6 C19 N8 110.9(3) . . ? N6 C19 H19 124.6 . . ? N8 C19 H19 124.6 . . ? N7 C20 N8 115.2(3) . . ? N7 C20 H20 122.4 . . ? N8 C20 H20 122.4 . . ? C22 O2 C25 109.8(7) . . ? C22 O2 C24 35.7(6) . 2_666 ? C25 O2 C24 74.6(7) . 2_666 ? C22 O2 C23 87.4(6) . 2_666 ? C25 O2 C23 23.5(6) . 2_666 ? C24 O2 C23 51.8(5) 2_666 2_666 ? C10 O1 C11 102.8(2) . . ? C24 C22 O2 82.9(13) 2_666 . ? C24 C22 C23 39.0(18) 2_666 . ? O2 C22 C23 104.3(10) . . ? C24 C22 H22A 150.0 2_666 . ? O2 C22 H22A 110.9 . . ? C23 C22 H22A 111.0 . . ? C24 C22 H22B 89.6 2_666 . ? O2 C22 H22B 110.4 . . ? C23 C22 H22B 111.4 . . ? H22A C22 H22B 108.8 . . ? C22 C23 C24 110.5(12) . . ? C22 C23 H23A 110.1 . . ? C24 C23 H23A 109.7 . . ? C22 C23 H23B 109.2 . . ? C24 C23 H23B 108.8 . . ? H23A C23 H23B 108.5 . . ? O2 C25 C24 111.5(9) . . ? O2 C25 H25A 109.8 . . ? C24 C25 H25A 110.6 . . ? O2 C25 H25B 108.3 . . ? C24 C25 H25B 108.3 . . ? H25A C25 H25B 108.3 . . ? C25 C24 C23 98.9(11) . . ? C25 C24 H24A 113.0 . . ? C23 C24 H24A 112.0 . . ? C25 C24 H24B 110.8 . . ? C23 C24 H24B 112.6 . . ? H24A C24 H24B 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 C2 N1 N2 C1 0.3(3) . . . . ? C3 N1 N2 C1 178.7(2) . . . . ? N8 Mn1 N3 C2 -121.0(2) . . . . ? N8 Mn1 N3 C2 59.0(2) 2_776 . . . ? N3 Mn1 N3 C2 70(100) 2_776 . . . ? Cl1 Mn1 N3 C2 -28.4(2) . . . . ? Cl1 Mn1 N3 C2 151.6(2) 2_776 . . . ? N8 Mn1 N3 C1 63.9(2) . . . . ? N8 Mn1 N3 C1 -116.1(2) 2_776 . . . ? N3 Mn1 N3 C1 -106(100) 2_776 . . . ? Cl1 Mn1 N3 C1 156.5(2) . . . . ? Cl1 Mn1 N3 C1 -23.5(2) 2_776 . . . ? C10 N4 N5 C11 0.2(3) . . . . ? C19 N6 N7 C20 -0.3(3) . . . . ? C18 N6 N7 C20 175.6(3) . . . . ? N8 Mn1 N8 C19 -55(100) 2_776 . . . ? N3 Mn1 N8 C19 130.4(2) 2_776 . . . ? N3 Mn1 N8 C19 -49.6(2) . . . . ? Cl1 Mn1 N8 C19 -141.9(2) . . . . ? Cl1 Mn1 N8 C19 38.1(2) 2_776 . . . ? N8 Mn1 N8 C20 123(100) 2_776 . . . ? N3 Mn1 N8 C20 -51.8(3) 2_776 . . . ? N3 Mn1 N8 C20 128.2(3) . . . . ? Cl1 Mn1 N8 C20 36.0(3) . . . . ? Cl1 Mn1 N8 C20 -144.0(3) 2_776 . . . ? N1 N2 C1 N3 -0.4(3) . . . . ? C2 N3 C1 N2 0.4(3) . . . . ? Mn1 N3 C1 N2 176.38(18) . . . . ? C1 N3 C2 N1 -0.2(3) . . . . ? Mn1 N3 C2 N1 -176.27(16) . . . . ? N2 N1 C2 N3 -0.1(3) . . . . ? C3 N1 C2 N3 -178.3(2) . . . . ? C2 N1 C3 C4 97.4(3) . . . . ? N2 N1 C3 C4 -80.7(3) . . . . ? N1 C3 C4 C9 2.9(4) . . . . ? N1 C3 C4 C5 -176.5(2) . . . . ? C9 C4 C5 C6 -1.1(4) . . . . ? C3 C4 C5 C6 178.3(3) . . . . ? C4 C5 C6 C7 0.5(5) . . . . ? C5 C6 C7 C8 0.0(4) . . . . ? C6 C7 C8 C9 0.0(4) . . . . ? C6 C7 C8 C10 -178.8(3) . . . . ? C5 C4 C9 C8 1.1(4) . . . . ? C3 C4 C9 C8 -178.3(3) . . . . ? C7 C8 C9 C4 -0.6(4) . . . . ? C10 C8 C9 C4 178.2(2) . . . . ? N5 N4 C10 O1 -0.4(3) . . . . ? N5 N4 C10 C8 177.7(3) . . . . ? C7 C8 C10 N4 5.7(4) . . . . ? C9 C8 C10 N4 -173.1(3) . . . . ? C7 C8 C10 O1 -176.3(2) . . . . ? C9 C8 C10 O1 4.9(4) . . . . ? N4 N5 C11 O1 0.1(3) . . . . ? N4 N5 C11 C12 178.7(3) . . . . ? N5 C11 C12 C17 179.9(3) . . . . ? O1 C11 C12 C17 -1.6(4) . . . . ? N5 C11 C12 C13 -0.7(5) . . . . ? O1 C11 C12 C13 177.8(2) . . . . ? C17 C12 C13 C14 0.5(4) . . . . ? C11 C12 C13 C14 -178.9(3) . . . . ? C12 C13 C14 C15 0.2(4) . . . . ? C13 C14 C15 C16 -0.9(4) . . . . ? C14 C15 C16 C17 0.7(4) . . . . ? C14 C15 C16 C18 -180.0(3) . . . . ? C13 C12 C17 C16 -0.7(4) . . . . ? C11 C12 C17 C16 178.7(2) . . . . ? C15 C16 C17 C12 0.1(4) . . . . ? C18 C16 C17 C12 -179.3(3) . . . . ? C19 N6 C18 C16 112.6(3) . . . . ? N7 N6 C18 C16 -62.3(4) . . . . ? C17 C16 C18 N6 -52.6(4) . . . . ? C15 C16 C18 N6 128.1(3) . . . . ? N7 N6 C19 N8 0.3(3) . . . . ? C18 N6 C19 N8 -175.1(3) . . . . ? C20 N8 C19 N6 -0.1(3) . . . . ? Mn1 N8 C19 N6 178.17(18) . . . . ? N6 N7 C20 N8 0.2(4) . . . . ? C19 N8 C20 N7 -0.1(4) . . . . ? Mn1 N8 C20 N7 -178.3(2) . . . . ? N4 C10 O1 C11 0.4(3) . . . . ? C8 C10 O1 C11 -177.9(2) . . . . ? N5 C11 O1 C10 -0.3(3) . . . . ? C12 C11 O1 C10 -179.1(2) . . . . ? C25 O2 C22 C23 -22.9(14) . . . . ? O2 C22 C23 C24 18(2) . . . . ? C22 O2 C25 C24 20.1(16) . . . . ? O2 C25 C24 C23 -7(2) . . . . ? C22 C23 C24 C25 -7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.439 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.065