data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Cu N8 Ni O4' _chemical_formula_weight 450.51 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' 'Ni' 'Ni' 0.3393 1.1124 '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 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 12.843(3) _cell_length_b 13.229(3) _cell_length_c 10.517(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.44(3) _cell_angle_gamma 90.00 _cell_volume 1730.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7855 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.729 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 900 _exptl_absorpt_coefficient_mu 2.353 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'SCX-MINI' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 8853 _diffrn_standards_interval_count none _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 8853 _diffrn_reflns_av_R_equivalents 0.0537 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.60 _reflns_number_total 1991 _reflns_number_gt 1630 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0419P)^2^+7.1860P] 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 1991 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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 Ni1 Ni 0.5000 0.64693(4) -0.2500 0.01645(16) Uani 1 2 d S . . Cu1 Cu 0.5000 0.5000 0.0000 0.02136(17) Uani 1 2 d S . . N4 N 0.3783(2) 0.7524(2) -0.2461(3) 0.0231(6) Uani 1 1 d . . . N1 N 0.5440(2) 0.6359(2) -0.0447(3) 0.0238(6) Uani 1 1 d . . . N2 N 0.5373(3) 0.7087(2) 0.0218(3) 0.0328(7) Uani 1 1 d . . . C5 C 0.2279(3) 0.7906(3) -0.1582(4) 0.0283(8) Uani 1 1 d . . . H5A H 0.1803 0.7692 -0.1100 0.034 Uiso 1 1 calc R . . C4 C 0.3075(3) 0.7270(3) -0.1765(4) 0.0276(8) Uani 1 1 d . . . H4A H 0.3127 0.6630 -0.1388 0.033 Uiso 1 1 calc R . . C3 C 0.3652(3) 0.8432(3) -0.3032(4) 0.0342(9) Uani 1 1 d . . . H3A H 0.4110 0.8614 -0.3554 0.041 Uiso 1 1 calc R . . N3 N 0.5308(4) 0.7783(3) 0.0826(4) 0.0633(12) Uani 1 1 d . . . O2 O 0.1046(2) 0.93748(19) -0.0833(2) 0.0325(6) Uani 1 1 d . . . C1 C 0.2189(3) 0.8862(3) -0.2118(3) 0.0237(7) Uani 1 1 d . . . C6 C 0.1367(3) 0.9589(2) -0.1838(3) 0.0215(7) Uani 1 1 d . . . C2 C 0.2879(3) 0.9117(3) -0.2894(4) 0.0356(9) Uani 1 1 d . . . H2A H 0.2821 0.9740 -0.3315 0.043 Uiso 1 1 calc R . . O1 O 0.10885(19) 1.03100(17) -0.2611(2) 0.0240(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0180(3) 0.0134(3) 0.0209(3) 0.000 0.0103(2) 0.000 Cu1 0.0259(3) 0.0180(3) 0.0249(3) 0.0038(2) 0.0154(2) 0.0054(2) N4 0.0239(15) 0.0220(14) 0.0263(15) 0.0009(12) 0.0121(12) 0.0040(12) N1 0.0280(16) 0.0206(14) 0.0264(15) 0.0006(12) 0.0134(13) 0.0000(12) N2 0.0447(19) 0.0284(17) 0.0256(16) 0.0002(14) 0.0092(14) -0.0030(15) C5 0.0302(19) 0.0253(18) 0.035(2) 0.0089(16) 0.0194(16) 0.0079(15) C4 0.033(2) 0.0213(17) 0.0339(19) 0.0072(15) 0.0181(16) 0.0079(15) C3 0.039(2) 0.032(2) 0.042(2) 0.0121(18) 0.0297(19) 0.0086(17) N3 0.105(4) 0.036(2) 0.050(2) -0.016(2) 0.022(2) -0.001(2) O2 0.0445(16) 0.0256(13) 0.0371(14) 0.0121(11) 0.0286(13) 0.0162(12) C1 0.0254(18) 0.0232(17) 0.0253(18) 0.0029(14) 0.0115(14) 0.0065(14) C6 0.0223(17) 0.0193(16) 0.0265(18) 0.0016(14) 0.0132(14) 0.0036(13) C2 0.041(2) 0.0257(19) 0.050(2) 0.0144(18) 0.030(2) 0.0121(17) O1 0.0274(13) 0.0197(12) 0.0294(13) 0.0057(10) 0.0155(11) 0.0061(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 Ni1 N1 2.096(3) . ? Ni1 N1 2.096(3) 2_654 ? Ni1 O1 2.098(2) 4_544 ? Ni1 O1 2.098(2) 3_545 ? Ni1 N4 2.103(3) 2_654 ? Ni1 N4 2.103(3) . ? Cu1 O2 1.960(2) 7_565 ? Cu1 O2 1.960(2) 3_545 ? Cu1 N1 1.976(3) 5_665 ? Cu1 N1 1.976(3) . ? N4 C3 1.335(4) . ? N4 C4 1.344(4) . ? N1 N2 1.206(4) . ? N2 N3 1.136(5) . ? C5 C4 1.375(5) . ? C5 C1 1.378(5) . ? C5 H5A 0.9300 . ? C4 H4A 0.9300 . ? C3 C2 1.377(5) . ? C3 H3A 0.9300 . ? O2 C6 1.258(4) . ? O2 Cu1 1.960(2) 3_455 ? C1 C2 1.388(5) . ? C1 C6 1.511(4) . ? C6 O1 1.247(4) . ? C2 H2A 0.9300 . ? O1 Ni1 2.098(2) 3_455 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 N1 172.00(15) . 2_654 ? N1 Ni1 O1 84.49(10) . 4_544 ? N1 Ni1 O1 89.65(10) 2_654 4_544 ? N1 Ni1 O1 89.65(10) . 3_545 ? N1 Ni1 O1 84.49(10) 2_654 3_545 ? O1 Ni1 O1 86.06(13) 4_544 3_545 ? N1 Ni1 N4 93.17(11) . 2_654 ? N1 Ni1 N4 92.14(11) 2_654 2_654 ? O1 Ni1 N4 174.16(11) 4_544 2_654 ? O1 Ni1 N4 88.59(10) 3_545 2_654 ? N1 Ni1 N4 92.14(11) . . ? N1 Ni1 N4 93.17(11) 2_654 . ? O1 Ni1 N4 88.59(10) 4_544 . ? O1 Ni1 N4 174.16(11) 3_545 . ? N4 Ni1 N4 96.86(16) 2_654 . ? O2 Cu1 O2 180.00(12) 7_565 3_545 ? O2 Cu1 N1 90.51(11) 7_565 5_665 ? O2 Cu1 N1 89.49(11) 3_545 5_665 ? O2 Cu1 N1 89.49(11) 7_565 . ? O2 Cu1 N1 90.51(11) 3_545 . ? N1 Cu1 N1 180.0 5_665 . ? C3 N4 C4 116.3(3) . . ? C3 N4 Ni1 126.8(2) . . ? C4 N4 Ni1 116.8(2) . . ? N2 N1 Cu1 121.5(2) . . ? N2 N1 Ni1 120.1(2) . . ? Cu1 N1 Ni1 106.79(13) . . ? N3 N2 N1 178.8(4) . . ? C4 C5 C1 119.6(3) . . ? C4 C5 H5A 120.2 . . ? C1 C5 H5A 120.2 . . ? N4 C4 C5 123.4(3) . . ? N4 C4 H4A 118.3 . . ? C5 C4 H4A 118.3 . . ? N4 C3 C2 123.9(3) . . ? N4 C3 H3A 118.1 . . ? C2 C3 H3A 118.1 . . ? C6 O2 Cu1 133.2(2) . 3_455 ? C5 C1 C2 117.5(3) . . ? C5 C1 C6 119.7(3) . . ? C2 C1 C6 122.7(3) . . ? O1 C6 O2 128.3(3) . . ? O1 C6 C1 117.4(3) . . ? O2 C6 C1 114.3(3) . . ? C3 C2 C1 119.0(3) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C6 O1 Ni1 127.6(2) . 3_455 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Ni1 N4 C3 126.4(3) . . . . ? N1 Ni1 N4 C3 -59.6(3) 2_654 . . . ? O1 Ni1 N4 C3 -149.1(3) 4_544 . . . ? O1 Ni1 N4 C3 -125.7(9) 3_545 . . . ? N4 Ni1 N4 C3 33.0(3) 2_654 . . . ? N1 Ni1 N4 C4 -52.0(3) . . . . ? N1 Ni1 N4 C4 122.1(3) 2_654 . . . ? O1 Ni1 N4 C4 32.5(3) 4_544 . . . ? O1 Ni1 N4 C4 55.9(11) 3_545 . . . ? N4 Ni1 N4 C4 -145.4(3) 2_654 . . . ? O2 Cu1 N1 N2 28.7(3) 7_565 . . . ? O2 Cu1 N1 N2 -151.3(3) 3_545 . . . ? N1 Cu1 N1 N2 136(100) 5_665 . . . ? O2 Cu1 N1 Ni1 -114.32(13) 7_565 . . . ? O2 Cu1 N1 Ni1 65.68(13) 3_545 . . . ? N1 Cu1 N1 Ni1 -7(100) 5_665 . . . ? N1 Ni1 N1 N2 -165.0(3) 2_654 . . . ? O1 Ni1 N1 N2 -121.9(3) 4_544 . . . ? O1 Ni1 N1 N2 152.1(3) 3_545 . . . ? N4 Ni1 N1 N2 63.5(3) 2_654 . . . ? N4 Ni1 N1 N2 -33.5(3) . . . . ? N1 Ni1 N1 Cu1 -21.35(10) 2_654 . . . ? O1 Ni1 N1 Cu1 21.81(12) 4_544 . . . ? O1 Ni1 N1 Cu1 -64.26(12) 3_545 . . . ? N4 Ni1 N1 Cu1 -152.83(13) 2_654 . . . ? N4 Ni1 N1 Cu1 110.18(13) . . . . ? Cu1 N1 N2 N3 -153(22) . . . . ? Ni1 N1 N2 N3 -15(22) . . . . ? C3 N4 C4 C5 -2.7(5) . . . . ? Ni1 N4 C4 C5 175.8(3) . . . . ? C1 C5 C4 N4 -0.7(6) . . . . ? C4 N4 C3 C2 3.0(6) . . . . ? Ni1 N4 C3 C2 -175.4(3) . . . . ? C4 C5 C1 C2 3.9(6) . . . . ? C4 C5 C1 C6 -175.7(3) . . . . ? Cu1 O2 C6 O1 0.8(6) 3_455 . . . ? Cu1 O2 C6 C1 -179.0(2) 3_455 . . . ? C5 C1 C6 O1 -159.5(3) . . . . ? C2 C1 C6 O1 21.0(5) . . . . ? C5 C1 C6 O2 20.3(5) . . . . ? C2 C1 C6 O2 -159.2(4) . . . . ? N4 C3 C2 C1 0.1(7) . . . . ? C5 C1 C2 C3 -3.6(6) . . . . ? C6 C1 C2 C3 175.9(4) . . . . ? O2 C6 O1 Ni1 1.7(5) . . . 3_455 ? C1 C6 O1 Ni1 -178.6(2) . . . 3_455 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.456 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.090 #====================end data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Co0.30 Cu N8 Ni0.70 O4' _chemical_formula_weight 450.58 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' 'Ni' 'Ni' 0.3393 1.1124 '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' 'Cu' 'Cu' 0.3201 1.2651 '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 12.868(3) _cell_length_b 13.351(3) _cell_length_c 10.526(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.39(3) _cell_angle_gamma 90.00 _cell_volume 1751.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7121 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 899 _exptl_absorpt_coefficient_mu 2.286 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7235 _diffrn_reflns_av_R_equivalents 0.1114 _diffrn_reflns_av_sigmaI/netI 0.0815 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1524 _reflns_number_gt 1187 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0722P)^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 1524 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0875 _refine_ls_R_factor_gt 0.0644 _refine_ls_wR_factor_ref 0.1520 _refine_ls_wR_factor_gt 0.1394 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 0.0000 0.0294(4) Uani 1 2 d S . . Co1 Co 0.0000 0.85321(7) 0.2500 0.0245(4) Uani 0.30 2 d SP . . Ni1 Ni 0.0000 0.85321(7) 0.2500 0.0245(4) Uani 0.70 2 d SP . . O1 O 0.3906(3) 0.4691(3) 0.2606(4) 0.0339(11) Uani 1 1 d . . . O2 O 0.3957(3) 0.5623(3) 0.0835(4) 0.0389(11) Uani 1 1 d . . . N4 N 0.1223(4) 0.7462(4) 0.2458(5) 0.0322(12) Uani 1 1 d . . . N1 N 0.5437(4) 0.6356(3) -0.0439(5) 0.0290(12) Uani 1 1 d . . . N2 N 0.5372(4) 0.7080(4) 0.0221(5) 0.0401(13) Uani 1 1 d . . . N3 N 0.5312(6) 0.7763(5) 0.0844(7) 0.075(2) Uani 1 1 d . . . C2 C 0.2808(5) 0.6138(4) 0.2125(6) 0.0301(14) Uani 1 1 d . . . C6 C 0.2119(5) 0.5888(5) 0.2876(7) 0.0457(19) Uani 1 1 d . . . H6A H 0.2163 0.5263 0.3278 0.055 Uiso 1 1 calc R . . C5 C 0.1354(5) 0.6577(5) 0.3030(7) 0.0419(18) Uani 1 1 d . . . H5A H 0.0908 0.6404 0.3568 0.050 Uiso 1 1 calc R . . C1 C 0.3626(5) 0.5419(4) 0.1837(6) 0.0308(15) Uani 1 1 d . . . C4 C 0.1926(5) 0.7724(4) 0.1766(6) 0.0348(15) Uani 1 1 d . . . H4A H 0.1877 0.8361 0.1397 0.042 Uiso 1 1 calc R . . C3 C 0.2715(5) 0.7089(4) 0.1584(6) 0.0351(15) Uani 1 1 d . . . H3A H 0.3187 0.7297 0.1096 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0251(6) 0.0288(6) 0.0397(7) 0.0033(4) 0.0182(5) 0.0051(4) Co1 0.0180(6) 0.0224(6) 0.0369(7) 0.000 0.0142(5) 0.000 Ni1 0.0180(6) 0.0224(6) 0.0369(7) 0.000 0.0142(5) 0.000 O1 0.024(2) 0.035(2) 0.049(3) 0.011(2) 0.020(2) 0.012(2) O2 0.042(3) 0.038(3) 0.048(3) 0.012(2) 0.031(2) 0.017(2) N4 0.026(3) 0.035(3) 0.039(3) 0.001(2) 0.014(3) 0.004(2) N1 0.028(3) 0.025(3) 0.037(3) 0.004(2) 0.012(3) 0.001(2) N2 0.040(3) 0.041(3) 0.041(3) -0.003(3) 0.014(3) 0.001(3) N3 0.102(6) 0.057(4) 0.067(5) -0.017(4) 0.023(5) 0.002(4) C2 0.025(3) 0.031(3) 0.034(3) 0.000(3) 0.006(3) 0.004(3) C6 0.045(4) 0.040(4) 0.066(5) 0.017(3) 0.041(4) 0.014(3) C5 0.036(4) 0.043(4) 0.057(4) 0.014(3) 0.031(4) 0.007(3) C1 0.019(3) 0.030(4) 0.045(4) 0.000(3) 0.011(3) 0.008(3) C4 0.034(4) 0.029(3) 0.049(4) 0.004(3) 0.023(3) 0.002(3) C3 0.032(4) 0.035(4) 0.045(4) 0.011(3) 0.021(3) 0.010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.962(4) . ? Cu1 O2 1.962(4) 5_665 ? Cu1 N1 1.984(5) 5_665 ? Cu1 N1 1.984(5) . ? Cu1 O1 2.596(4) 2_655 ? Cu1 O1 2.596(4) 6_565 ? Co1 N1 2.106(5) 8_466 ? Co1 N1 2.106(5) 7_565 ? Co1 O1 2.113(4) 4 ? Co1 O1 2.113(4) 3_455 ? Co1 N4 2.134(5) 2 ? Co1 N4 2.134(5) . ? O1 C1 1.258(7) . ? O1 Ni1 2.113(4) 3_545 ? O1 Co1 2.113(4) 3_545 ? O1 Cu1 2.596(4) 2_655 ? O2 C1 1.263(7) . ? N4 C5 1.318(8) . ? N4 C4 1.341(7) . ? N1 N2 1.205(7) . ? N1 Ni1 2.106(5) 7_565 ? N1 Co1 2.106(5) 7_565 ? N2 N3 1.137(7) . ? C2 C6 1.367(8) . ? C2 C3 1.385(8) . ? C2 C1 1.509(8) . ? C6 C5 1.386(9) . ? C4 C3 1.373(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 O2 Cu1 O2 180.0 . 5_665 ? O2 Cu1 N1 91.01(18) . 5_665 ? O2 Cu1 N1 88.99(18) 5_665 5_665 ? O2 Cu1 N1 88.99(18) . . ? O2 Cu1 N1 91.01(18) 5_665 . ? N1 Cu1 N1 180.0 5_665 . ? O2 Cu1 O1 84.19(15) . 2_655 ? O2 Cu1 O1 95.81(15) 5_665 2_655 ? N1 Cu1 O1 75.25(17) 5_665 2_655 ? N1 Cu1 O1 104.75(17) . 2_655 ? O2 Cu1 O1 95.81(15) . 6_565 ? O2 Cu1 O1 84.19(15) 5_665 6_565 ? N1 Cu1 O1 104.75(17) 5_665 6_565 ? N1 Cu1 O1 75.25(17) . 6_565 ? O1 Cu1 O1 180.0 2_655 6_565 ? N1 Co1 N1 171.9(3) 8_466 7_565 ? N1 Co1 O1 89.52(17) 8_466 4 ? N1 Co1 O1 84.53(17) 7_565 4 ? N1 Co1 O1 84.53(17) 8_466 3_455 ? N1 Co1 O1 89.52(17) 7_565 3_455 ? O1 Co1 O1 85.9(2) 4 3_455 ? N1 Co1 N4 92.04(18) 8_466 2 ? N1 Co1 N4 93.40(19) 7_565 2 ? O1 Co1 N4 174.60(18) 4 2 ? O1 Co1 N4 89.15(18) 3_455 2 ? N1 Co1 N4 93.40(19) 8_466 . ? N1 Co1 N4 92.04(18) 7_565 . ? O1 Co1 N4 89.15(18) 4 . ? O1 Co1 N4 174.60(18) 3_455 . ? N4 Co1 N4 95.9(3) 2 . ? C1 O1 Ni1 128.3(4) . 3_545 ? C1 O1 Co1 128.3(4) . 3_545 ? Ni1 O1 Co1 0.00(4) 3_545 3_545 ? C1 O1 Cu1 120.0(4) . 2_655 ? Ni1 O1 Cu1 87.71(14) 3_545 2_655 ? Co1 O1 Cu1 87.71(14) 3_545 2_655 ? C1 O2 Cu1 133.9(4) . . ? C5 N4 C4 117.1(5) . . ? C5 N4 Co1 127.1(4) . . ? C4 N4 Co1 115.9(4) . . ? N2 N1 Cu1 122.2(4) . . ? N2 N1 Ni1 119.9(4) . 7_565 ? Cu1 N1 Ni1 106.6(2) . 7_565 ? N2 N1 Co1 119.9(4) . 7_565 ? Cu1 N1 Co1 106.6(2) . 7_565 ? Ni1 N1 Co1 0.00(5) 7_565 7_565 ? N3 N2 N1 179.9(8) . . ? C6 C2 C3 117.3(5) . . ? C6 C2 C1 123.0(6) . . ? C3 C2 C1 119.6(5) . . ? C2 C6 C5 119.2(6) . . ? N4 C5 C6 123.8(6) . . ? O1 C1 O2 126.9(5) . . ? O1 C1 C2 117.7(5) . . ? O2 C1 C2 115.3(5) . . ? N4 C4 C3 122.4(6) . . ? C4 C3 C2 120.1(6) . . ? 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 O2 Cu1 O2 C1 142(100) 5_665 . . . ? N1 Cu1 O2 C1 36.6(6) 5_665 . . . ? N1 Cu1 O2 C1 -143.4(6) . . . . ? O1 Cu1 O2 C1 -38.4(6) 2_655 . . . ? O1 Cu1 O2 C1 141.6(6) 6_565 . . . ? N1 Co1 N4 C5 58.7(6) 8_466 . . . ? N1 Co1 N4 C5 -127.3(6) 7_565 . . . ? O1 Co1 N4 C5 148.2(6) 4 . . . ? O1 Co1 N4 C5 126.0(17) 3_455 . . . ? N4 Co1 N4 C5 -33.7(5) 2 . . . ? N1 Co1 N4 C4 -121.7(4) 8_466 . . . ? N1 Co1 N4 C4 52.3(4) 7_565 . . . ? O1 Co1 N4 C4 -32.2(4) 4 . . . ? O1 Co1 N4 C4 -54.4(19) 3_455 . . . ? N4 Co1 N4 C4 145.9(5) 2 . . . ? O2 Cu1 N1 N2 28.8(5) . . . . ? O2 Cu1 N1 N2 -151.2(5) 5_665 . . . ? N1 Cu1 N1 N2 124(100) 5_665 . . . ? O1 Cu1 N1 N2 -54.9(5) 2_655 . . . ? O1 Cu1 N1 N2 125.1(5) 6_565 . . . ? O2 Cu1 N1 Ni1 -114.6(2) . . . 7_565 ? O2 Cu1 N1 Ni1 65.4(2) 5_665 . . 7_565 ? N1 Cu1 N1 Ni1 -20(100) 5_665 . . 7_565 ? O1 Cu1 N1 Ni1 161.67(17) 2_655 . . 7_565 ? O1 Cu1 N1 Ni1 -18.33(17) 6_565 . . 7_565 ? O2 Cu1 N1 Co1 -114.6(2) . . . 7_565 ? O2 Cu1 N1 Co1 65.4(2) 5_665 . . 7_565 ? N1 Cu1 N1 Co1 -20(100) 5_665 . . 7_565 ? O1 Cu1 N1 Co1 161.67(17) 2_655 . . 7_565 ? O1 Cu1 N1 Co1 -18.33(17) 6_565 . . 7_565 ? Cu1 N1 N2 N3 116(100) . . . . ? Ni1 N1 N2 N3 -105(100) 7_565 . . . ? Co1 N1 N2 N3 -105(100) 7_565 . . . ? C3 C2 C6 C5 1.6(10) . . . . ? C1 C2 C6 C5 -176.5(6) . . . . ? C4 N4 C5 C6 -4.9(10) . . . . ? Co1 N4 C5 C6 174.8(5) . . . . ? C2 C6 C5 N4 2.2(11) . . . . ? Ni1 O1 C1 O2 -1.2(10) 3_545 . . . ? Co1 O1 C1 O2 -1.2(10) 3_545 . . . ? Cu1 O1 C1 O2 112.3(6) 2_655 . . . ? Ni1 O1 C1 C2 178.9(4) 3_545 . . . ? Co1 O1 C1 C2 178.9(4) 3_545 . . . ? Cu1 O1 C1 C2 -67.6(6) 2_655 . . . ? Cu1 O2 C1 O1 -0.8(10) . . . . ? Cu1 O2 C1 C2 179.0(4) . . . . ? C6 C2 C1 O1 -21.7(9) . . . . ? C3 C2 C1 O1 160.3(6) . . . . ? C6 C2 C1 O2 158.5(6) . . . . ? C3 C2 C1 O2 -19.6(8) . . . . ? C5 N4 C4 C3 3.8(9) . . . . ? Co1 N4 C4 C3 -175.9(5) . . . . ? N4 C4 C3 C2 -0.1(9) . . . . ? C6 C2 C3 C4 -2.6(9) . . . . ? C1 C2 C3 C4 175.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.989 _refine_diff_density_min -1.134 _refine_diff_density_rms 0.136 #====================end data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Co0.50 Cu N8 Ni0.50 O4' _chemical_formula_weight 450.62 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' 'Ni' 'Ni' 0.3393 1.1124 '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 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 12.848(3) _cell_length_b 13.275(3) _cell_length_c 10.443(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.45(3) _cell_angle_gamma 90.00 _cell_volume 1724.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7163 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.7 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.735 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 898 _exptl_absorpt_coefficient_mu 2.296 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7177 _diffrn_reflns_av_R_equivalents 0.1013 _diffrn_reflns_av_sigmaI/netI 0.0735 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1511 _reflns_number_gt 1155 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0422P)^2^+0.7877P] 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 1511 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0922 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.5000 0.35253(7) 0.2500 0.0207(3) Uani 0.50 2 d SP . . Co1 Co 0.5000 0.35253(7) 0.2500 0.0207(3) Uani 0.50 2 d SP . . O2 O 0.3950(3) 0.5618(3) 0.0827(4) 0.0362(11) Uani 1 1 d . . . N1 N 0.4565(4) 0.3641(3) 0.0453(5) 0.0269(11) Uani 1 1 d . . . C1 C 0.3630(4) 0.5402(4) 0.1828(6) 0.0269(14) Uani 1 1 d . . . Cu1 Cu 0.5000 0.5000 0.0000 0.0260(3) Uani 1 2 d S . . O1 O 0.3912(3) 0.4690(3) 0.2609(4) 0.0272(10) Uani 1 1 d . . . N2 N 0.4631(4) 0.2915(4) -0.0231(5) 0.0375(13) Uani 1 1 d . . . C2 C 0.2803(4) 0.6128(4) 0.2120(5) 0.0268(14) Uani 1 1 d . . . N3 N 0.4689(6) 0.2218(4) -0.0842(6) 0.070(2) Uani 1 1 d . . . C3 C 0.2706(5) 0.7082(4) 0.1575(6) 0.0320(15) Uani 1 1 d . . . H3A H 0.3171 0.7294 0.1076 0.038 Uiso 1 1 calc R . . N4 N 0.1226(4) 0.7457(3) 0.2456(4) 0.0281(12) Uani 1 1 d . . . C4 C 0.1929(5) 0.7707(4) 0.1773(6) 0.0309(14) Uani 1 1 d . . . H4A H 0.1886 0.8349 0.1409 0.037 Uiso 1 1 calc R . . C5 C 0.1353(5) 0.6554(4) 0.3031(6) 0.0395(17) Uani 1 1 d . . . H5A H 0.0898 0.6374 0.3560 0.047 Uiso 1 1 calc R . . C6 C 0.2118(5) 0.5877(4) 0.2884(6) 0.0388(17) Uani 1 1 d . . . H6A H 0.2172 0.5252 0.3299 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0232(6) 0.0145(6) 0.0279(6) 0.000 0.0133(5) 0.000 Co1 0.0232(6) 0.0145(6) 0.0279(6) 0.000 0.0133(5) 0.000 O2 0.055(3) 0.020(2) 0.045(3) 0.0113(19) 0.035(2) 0.014(2) N1 0.033(3) 0.019(3) 0.034(3) 0.000(2) 0.017(2) 0.002(2) C1 0.027(4) 0.020(3) 0.036(4) 0.001(3) 0.014(3) 0.003(3) Cu1 0.0329(6) 0.0184(6) 0.0326(6) 0.0035(4) 0.0190(5) 0.0052(5) O1 0.029(2) 0.020(2) 0.036(2) 0.0085(18) 0.015(2) 0.0099(18) N2 0.048(4) 0.033(3) 0.031(3) 0.004(3) 0.008(3) -0.001(3) C2 0.029(3) 0.025(3) 0.028(3) 0.005(3) 0.012(3) 0.006(3) N3 0.111(6) 0.042(4) 0.059(4) -0.020(4) 0.025(4) -0.003(4) C3 0.035(4) 0.030(3) 0.038(4) 0.013(3) 0.022(3) 0.013(3) N4 0.032(3) 0.025(3) 0.032(3) 0.003(2) 0.016(2) 0.006(2) C4 0.037(4) 0.021(3) 0.041(4) 0.008(3) 0.020(3) 0.007(3) C5 0.049(4) 0.032(4) 0.050(4) 0.009(3) 0.036(4) 0.007(3) C6 0.046(4) 0.020(4) 0.062(5) 0.015(3) 0.034(4) 0.012(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 2.076(5) 2_655 ? Ni1 N1 2.076(5) . ? Ni1 O1 2.107(3) 2_655 ? Ni1 O1 2.107(3) . ? Ni1 N4 2.128(4) 4_545 ? Ni1 N4 2.128(4) 3_545 ? O2 C1 1.248(6) . ? O2 Cu1 1.954(4) . ? N1 N2 1.216(6) . ? N1 Cu1 1.981(4) . ? C1 O1 1.241(6) . ? C1 C2 1.521(7) . ? Cu1 O2 1.954(4) 5_665 ? Cu1 N1 1.981(4) 5_665 ? Cu1 O1 2.572(4) 6_565 ? Cu1 O1 2.572(4) 2_655 ? O1 Cu1 2.572(4) 2_655 ? N2 N3 1.137(7) . ? C2 C6 1.367(7) . ? C2 C3 1.382(7) . ? C3 C4 1.352(7) . ? C3 H3A 0.9300 . ? N4 C4 1.325(6) . ? N4 C5 1.333(7) . ? N4 Co1 2.128(4) 3_455 ? N4 Ni1 2.128(4) 3_455 ? C4 H4A 0.9300 . ? C5 C6 1.368(7) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 N1 171.5(3) 2_655 . ? N1 Ni1 O1 89.40(16) 2_655 2_655 ? N1 Ni1 O1 84.37(16) . 2_655 ? N1 Ni1 O1 84.37(16) 2_655 . ? N1 Ni1 O1 89.40(16) . . ? O1 Ni1 O1 85.6(2) 2_655 . ? N1 Ni1 N4 92.15(17) 2_655 4_545 ? N1 Ni1 N4 93.50(18) . 4_545 ? O1 Ni1 N4 174.20(17) 2_655 4_545 ? O1 Ni1 N4 89.04(16) . 4_545 ? N1 Ni1 N4 93.50(18) 2_655 3_545 ? N1 Ni1 N4 92.15(17) . 3_545 ? O1 Ni1 N4 89.04(16) 2_655 3_545 ? O1 Ni1 N4 174.20(17) . 3_545 ? N4 Ni1 N4 96.4(3) 4_545 3_545 ? C1 O2 Cu1 133.0(4) . . ? N2 N1 Cu1 121.1(4) . . ? N2 N1 Ni1 120.4(4) . . ? Cu1 N1 Ni1 107.1(2) . . ? O1 C1 O2 128.4(5) . . ? O1 C1 C2 117.0(5) . . ? O2 C1 C2 114.6(5) . . ? O2 Cu1 O2 180.0 . 5_665 ? O2 Cu1 N1 89.45(16) . 5_665 ? O2 Cu1 N1 90.55(16) 5_665 5_665 ? O2 Cu1 N1 90.55(16) . . ? O2 Cu1 N1 89.45(16) 5_665 . ? N1 Cu1 N1 180.0 5_665 . ? O2 Cu1 O1 95.39(14) . 6_565 ? O2 Cu1 O1 84.61(14) 5_665 6_565 ? N1 Cu1 O1 74.93(16) 5_665 6_565 ? N1 Cu1 O1 105.07(16) . 6_565 ? O2 Cu1 O1 84.61(14) . 2_655 ? O2 Cu1 O1 95.39(14) 5_665 2_655 ? N1 Cu1 O1 105.07(16) 5_665 2_655 ? N1 Cu1 O1 74.93(16) . 2_655 ? O1 Cu1 O1 180.00(15) 6_565 2_655 ? C1 O1 Ni1 127.7(4) . . ? C1 O1 Cu1 120.9(4) . 2_655 ? Ni1 O1 Cu1 87.83(13) . 2_655 ? N3 N2 N1 178.0(6) . . ? C6 C2 C3 117.3(5) . . ? C6 C2 C1 123.1(5) . . ? C3 C2 C1 119.6(5) . . ? C4 C3 C2 119.6(5) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? C4 N4 C5 116.3(5) . . ? C4 N4 Co1 116.9(4) . 3_455 ? C5 N4 Co1 126.7(4) . 3_455 ? C4 N4 Ni1 116.9(4) . 3_455 ? C5 N4 Ni1 126.7(4) . 3_455 ? Co1 N4 Ni1 0.0 3_455 3_455 ? N4 C4 C3 123.9(5) . . ? N4 C4 H4A 118.1 . . ? C3 C4 H4A 118.1 . . ? N4 C5 C6 123.5(5) . . ? N4 C5 H5A 118.3 . . ? C6 C5 H5A 118.3 . . ? C2 C6 C5 119.3(5) . . ? C2 C6 H6A 120.3 . . ? C5 C6 H6A 120.3 . . ? 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 N1 Ni1 N1 N2 165.0(4) 2_655 . . . ? O1 Ni1 N1 N2 122.1(4) 2_655 . . . ? O1 Ni1 N1 N2 -152.3(4) . . . . ? N4 Ni1 N1 N2 -63.3(4) 4_545 . . . ? N4 Ni1 N1 N2 33.2(5) 3_545 . . . ? N1 Ni1 N1 Cu1 21.12(16) 2_655 . . . ? O1 Ni1 N1 Cu1 -21.80(19) 2_655 . . . ? O1 Ni1 N1 Cu1 63.8(2) . . . . ? N4 Ni1 N1 Cu1 152.8(2) 4_545 . . . ? N4 Ni1 N1 Cu1 -110.6(2) 3_545 . . . ? Cu1 O2 C1 O1 -0.3(10) . . . . ? Cu1 O2 C1 C2 178.6(4) . . . . ? C1 O2 Cu1 O2 39(100) . . . 5_665 ? C1 O2 Cu1 N1 -143.3(6) . . . 5_665 ? C1 O2 Cu1 N1 36.7(6) . . . . ? C1 O2 Cu1 O1 141.9(5) . . . 6_565 ? C1 O2 Cu1 O1 -38.1(5) . . . 2_655 ? N2 N1 Cu1 O2 150.4(5) . . . . ? Ni1 N1 Cu1 O2 -66.0(2) . . . . ? N2 N1 Cu1 O2 -29.6(5) . . . 5_665 ? Ni1 N1 Cu1 O2 114.0(2) . . . 5_665 ? N2 N1 Cu1 N1 -24(100) . . . 5_665 ? Ni1 N1 Cu1 N1 119(100) . . . 5_665 ? N2 N1 Cu1 O1 54.7(5) . . . 6_565 ? Ni1 N1 Cu1 O1 -161.73(16) . . . 6_565 ? N2 N1 Cu1 O1 -125.3(5) . . . 2_655 ? Ni1 N1 Cu1 O1 18.27(16) . . . 2_655 ? O2 C1 O1 Ni1 -2.8(9) . . . . ? C2 C1 O1 Ni1 178.3(3) . . . . ? O2 C1 O1 Cu1 111.3(6) . . . 2_655 ? C2 C1 O1 Cu1 -67.6(6) . . . 2_655 ? N1 Ni1 O1 C1 144.3(5) 2_655 . . . ? N1 Ni1 O1 C1 -29.9(5) . . . . ? O1 Ni1 O1 C1 54.5(4) 2_655 . . . ? N4 Ni1 O1 C1 -123.5(5) 4_545 . . . ? N4 Ni1 O1 C1 75.6(17) 3_545 . . . ? N1 Ni1 O1 Cu1 15.87(14) 2_655 . . 2_655 ? N1 Ni1 O1 Cu1 -158.36(15) . . . 2_655 ? O1 Ni1 O1 Cu1 -73.96(12) 2_655 . . 2_655 ? N4 Ni1 O1 Cu1 108.12(14) 4_545 . . 2_655 ? N4 Ni1 O1 Cu1 -52.9(16) 3_545 . . 2_655 ? Cu1 N1 N2 N3 167(20) . . . . ? Ni1 N1 N2 N3 28(21) . . . . ? O1 C1 C2 C6 -22.0(9) . . . . ? O2 C1 C2 C6 159.0(6) . . . . ? O1 C1 C2 C3 159.5(5) . . . . ? O2 C1 C2 C3 -19.5(8) . . . . ? C6 C2 C3 C4 -2.3(9) . . . . ? C1 C2 C3 C4 176.2(5) . . . . ? C5 N4 C4 C3 4.0(9) . . . . ? Co1 N4 C4 C3 -175.2(5) 3_455 . . . ? Ni1 N4 C4 C3 -175.2(5) 3_455 . . . ? C2 C3 C4 N4 -1.0(9) . . . . ? C4 N4 C5 C6 -3.8(9) . . . . ? Co1 N4 C5 C6 175.3(5) 3_455 . . . ? Ni1 N4 C5 C6 175.3(5) 3_455 . . . ? C3 C2 C6 C5 2.5(9) . . . . ? C1 C2 C6 C5 -176.0(6) . . . . ? N4 C5 C6 C2 0.6(10) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.518 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.102 #====================end data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Co0.60 Cu N8 Ni0.40 O4' _chemical_formula_weight 450.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' 'Ni' 'Ni' 0.3393 1.1124 '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 12.890(3) _cell_length_b 13.350(3) _cell_length_c 10.496(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.45(3) _cell_angle_gamma 90.00 _cell_volume 1749.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8004 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour dark _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.711 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 898 _exptl_absorpt_coefficient_mu 2.251 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7429 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1535 _reflns_number_gt 1302 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0237P)^2^+3.9377P] 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 1535 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0687 _refine_ls_wR_factor_gt 0.0657 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _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 Ni1 Ni 0.5000 0.35290(4) 0.2500 0.01470(17) Uani 0.40 2 d SP . . Co1 Co 0.5000 0.35290(4) 0.2500 0.01470(17) Uani 0.60 2 d SP . . O2 O 0.39534(19) 0.56217(17) 0.0829(2) 0.0304(6) Uani 1 1 d . . . N1 N 0.4565(2) 0.36466(19) 0.0441(3) 0.0222(6) Uani 1 1 d . . . C1 C 0.3629(2) 0.5415(2) 0.1840(3) 0.0194(7) Uani 1 1 d . . . Cu1 Cu 0.5000 0.5000 0.0000 0.01984(17) Uani 1 2 d S . . O1 O 0.39086(17) 0.46942(16) 0.2611(2) 0.0224(5) Uani 1 1 d . . . N2 N 0.4626(2) 0.2920(2) -0.0228(3) 0.0318(7) Uani 1 1 d . . . C2 C 0.2808(3) 0.6137(2) 0.2113(3) 0.0209(7) Uani 1 1 d . . . N3 N 0.4690(4) 0.2225(3) -0.0836(4) 0.0645(12) Uani 1 1 d . . . C3 C 0.2721(3) 0.7086(2) 0.1585(3) 0.0261(8) Uani 1 1 d . . . H3A H 0.3197 0.7301 0.1108 0.031 Uiso 1 1 calc R . . N4 N 0.1224(2) 0.7458(2) 0.2463(3) 0.0213(6) Uani 1 1 d . . . C4 C 0.1925(3) 0.7711(2) 0.1768(3) 0.0266(8) Uani 1 1 d . . . H4A H 0.1870 0.8345 0.1389 0.032 Uiso 1 1 calc R . . C5 C 0.1347(3) 0.6556(3) 0.3024(4) 0.0339(9) Uani 1 1 d . . . H5A H 0.0887 0.6371 0.3538 0.041 Uiso 1 1 calc R . . C6 C 0.2122(3) 0.5880(3) 0.2881(4) 0.0347(10) Uani 1 1 d . . . H6A H 0.2181 0.5260 0.3298 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0159(3) 0.0106(3) 0.0206(3) 0.000 0.0102(3) 0.000 Co1 0.0159(3) 0.0106(3) 0.0206(3) 0.000 0.0102(3) 0.000 O2 0.0392(15) 0.0261(13) 0.0355(14) 0.0113(11) 0.0273(13) 0.0175(11) N1 0.0291(17) 0.0164(15) 0.0245(15) -0.0026(13) 0.0132(13) 0.0011(12) C1 0.0176(17) 0.0174(17) 0.0256(19) 0.0015(15) 0.0101(15) 0.0024(14) Cu1 0.0238(3) 0.0158(3) 0.0245(3) 0.0037(2) 0.0147(3) 0.0053(2) O1 0.0245(13) 0.0185(12) 0.0280(13) 0.0063(10) 0.0136(11) 0.0071(10) N2 0.0400(19) 0.0290(18) 0.0251(16) 0.0015(15) 0.0058(14) -0.0020(15) C2 0.0210(18) 0.0226(18) 0.0204(17) 0.0024(15) 0.0078(14) 0.0061(14) N3 0.111(4) 0.035(2) 0.047(2) -0.019(2) 0.019(2) 0.000(2) C3 0.0290(19) 0.0241(18) 0.031(2) 0.0102(16) 0.0194(16) 0.0082(16) N4 0.0213(15) 0.0198(15) 0.0262(15) 0.0011(12) 0.0122(13) 0.0022(12) C4 0.031(2) 0.0172(17) 0.036(2) 0.0070(16) 0.0176(17) 0.0060(15) C5 0.036(2) 0.031(2) 0.045(2) 0.0101(18) 0.0295(19) 0.0067(18) C6 0.038(2) 0.025(2) 0.051(2) 0.0179(18) 0.029(2) 0.0147(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 2.099(3) . ? Ni1 N1 2.099(3) 2_655 ? Ni1 O1 2.120(2) 2_655 ? Ni1 O1 2.120(2) . ? Ni1 N4 2.137(3) 3_545 ? Ni1 N4 2.137(3) 4_545 ? O2 C1 1.265(4) . ? O2 Cu1 1.962(2) . ? N1 N2 1.211(4) . ? N1 Cu1 1.981(3) . ? C1 O1 1.252(4) . ? C1 C2 1.510(4) . ? Cu1 O2 1.962(2) 5_665 ? Cu1 N1 1.981(3) 5_665 ? Cu1 O1 2.583(2) 6_565 ? Cu1 O1 2.583(2) 2_655 ? O1 Cu1 2.583(2) 2_655 ? N2 N3 1.141(4) . ? C2 C3 1.376(4) . ? C2 C6 1.381(4) . ? C3 C4 1.373(4) . ? N4 C5 1.333(4) . ? N4 C4 1.338(4) . ? N4 Co1 2.137(3) 3_455 ? N4 Ni1 2.137(3) 3_455 ? C5 C6 1.381(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 N1 171.42(15) . 2_655 ? N1 Ni1 O1 84.21(10) . 2_655 ? N1 Ni1 O1 89.49(10) 2_655 2_655 ? N1 Ni1 O1 89.49(10) . . ? N1 Ni1 O1 84.21(10) 2_655 . ? O1 Ni1 O1 85.59(12) 2_655 . ? N1 Ni1 N4 92.30(10) . 3_545 ? N1 Ni1 N4 93.44(11) 2_655 3_545 ? O1 Ni1 N4 89.24(9) 2_655 3_545 ? O1 Ni1 N4 174.34(10) . 3_545 ? N1 Ni1 N4 93.44(11) . 4_545 ? N1 Ni1 N4 92.30(10) 2_655 4_545 ? O1 Ni1 N4 174.34(10) 2_655 4_545 ? O1 Ni1 N4 89.24(9) . 4_545 ? N4 Ni1 N4 96.00(14) 3_545 4_545 ? C1 O2 Cu1 133.5(2) . . ? N2 N1 Cu1 122.1(2) . . ? N2 N1 Ni1 119.8(2) . . ? Cu1 N1 Ni1 106.87(12) . . ? O1 C1 O2 127.5(3) . . ? O1 C1 C2 118.0(3) . . ? O2 C1 C2 114.5(3) . . ? O2 Cu1 O2 180.00(9) 5_665 . ? O2 Cu1 N1 89.08(10) 5_665 . ? O2 Cu1 N1 90.92(10) . . ? O2 Cu1 N1 90.92(10) 5_665 5_665 ? O2 Cu1 N1 89.08(10) . 5_665 ? N1 Cu1 N1 180.00(15) . 5_665 ? O2 Cu1 O1 84.53(9) 5_665 6_565 ? O2 Cu1 O1 95.47(9) . 6_565 ? N1 Cu1 O1 104.68(9) . 6_565 ? N1 Cu1 O1 75.32(9) 5_665 6_565 ? O2 Cu1 O1 95.47(9) 5_665 2_655 ? O2 Cu1 O1 84.53(9) . 2_655 ? N1 Cu1 O1 75.32(9) . 2_655 ? N1 Cu1 O1 104.68(9) 5_665 2_655 ? O1 Cu1 O1 180.00(9) 6_565 2_655 ? C1 O1 Ni1 128.1(2) . . ? C1 O1 Cu1 120.4(2) . 2_655 ? Ni1 O1 Cu1 87.78(8) . 2_655 ? N3 N2 N1 178.7(4) . . ? C3 C2 C6 117.7(3) . . ? C3 C2 C1 120.1(3) . . ? C6 C2 C1 122.2(3) . . ? C4 C3 C2 119.5(3) . . ? C5 N4 C4 116.5(3) . . ? C5 N4 Co1 127.2(2) . 3_455 ? C4 N4 Co1 116.3(2) . 3_455 ? C5 N4 Ni1 127.2(2) . 3_455 ? C4 N4 Ni1 116.3(2) . 3_455 ? Co1 N4 Ni1 0.0 3_455 3_455 ? N4 C4 C3 123.5(3) . . ? N4 C5 C6 123.5(3) . . ? C2 C6 C5 119.1(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.498 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.075 #====================end data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Co Cu N8 O4' _chemical_formula_weight 450.73 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' 'Cu' 'Cu' 0.3201 1.2651 '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 12.969(3) _cell_length_b 13.361(3) _cell_length_c 10.446(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.39(3) _cell_angle_gamma 90.00 _cell_volume 1753.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8392 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 2.195 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7357 _diffrn_reflns_av_R_equivalents 0.0673 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1534 _reflns_number_gt 1356 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0363P)^2^+2.6252P] 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 1534 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1029 _refine_ls_wR_factor_gt 0.0980 _refine_ls_goodness_of_fit_ref 1.255 _refine_ls_restrained_S_all 1.255 _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 O1 O 0.8917(2) 1.0306(2) 0.7616(3) 0.0282(8) Uani 1 1 d . . . Co1 Co 0.5000 0.64796(6) 0.7500 0.0201(3) Uani 1 2 d S . . Cu1 Cu 0.5000 0.5000 1.0000 0.0252(3) Uani 1 2 d S . . O2 O 0.8950(3) 0.9386(2) 0.5821(3) 0.0357(9) Uani 1 1 d . . . N4 N 0.6225(3) 0.7564(3) 0.7458(4) 0.0269(9) Uani 1 1 d . . . N1 N 0.5429(3) 0.6359(3) 0.9570(4) 0.0251(9) Uani 1 1 d . . . C1 C 0.7803(4) 0.8877(3) 0.7111(4) 0.0247(11) Uani 1 1 d . . . N2 N 0.5368(3) 0.7085(3) 1.0251(4) 0.0371(10) Uani 1 1 d . . . C3 C 0.6354(4) 0.8471(4) 0.8022(5) 0.0394(14) Uani 1 1 d . . . H3A H 0.5893 0.8661 0.8532 0.047 Uiso 1 1 calc R . . C2 C 0.7128(4) 0.9135(4) 0.7889(5) 0.0415(14) Uani 1 1 d . . . H2A H 0.7195 0.9750 0.8317 0.050 Uiso 1 1 calc R . . C6 C 0.8628(3) 0.9596(3) 0.6831(4) 0.0236(11) Uani 1 1 d . . . C5 C 0.7714(4) 0.7927(3) 0.6583(5) 0.0301(11) Uani 1 1 d . . . H5A H 0.8187 0.7709 0.6103 0.036 Uiso 1 1 calc R . . C4 C 0.6923(4) 0.7306(3) 0.6769(5) 0.0321(12) Uani 1 1 d . . . H4A H 0.6870 0.6671 0.6394 0.039 Uiso 1 1 calc R . . N3 N 0.5305(5) 0.7772(4) 1.0871(5) 0.0692(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0308(19) 0.0241(17) 0.0355(19) -0.0081(15) 0.0192(16) -0.0096(15) Co1 0.0207(5) 0.0176(5) 0.0259(5) 0.000 0.0134(4) 0.000 Cu1 0.0299(5) 0.0221(5) 0.0296(5) 0.0034(4) 0.0185(4) 0.0049(3) O2 0.045(2) 0.0317(19) 0.042(2) -0.0119(17) 0.0317(18) -0.0154(16) N4 0.026(2) 0.027(2) 0.031(2) -0.0011(18) 0.0137(18) -0.0043(18) N1 0.031(2) 0.020(2) 0.028(2) 0.0022(18) 0.0149(18) 0.0024(17) C1 0.028(3) 0.026(2) 0.024(2) -0.004(2) 0.013(2) -0.007(2) N2 0.045(3) 0.036(3) 0.031(2) 0.003(2) 0.011(2) 0.002(2) C3 0.043(3) 0.033(3) 0.055(3) -0.015(3) 0.036(3) -0.010(3) C2 0.049(3) 0.030(3) 0.057(4) -0.016(3) 0.035(3) -0.012(3) C6 0.020(3) 0.025(2) 0.029(3) 0.003(2) 0.010(2) -0.002(2) C5 0.031(3) 0.030(3) 0.036(3) -0.007(2) 0.021(2) -0.006(2) C4 0.037(3) 0.027(3) 0.040(3) -0.006(2) 0.022(2) -0.007(2) N3 0.113(5) 0.040(3) 0.056(3) -0.017(3) 0.024(3) 0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.249(5) . ? O1 Co1 2.129(3) 3 ? Co1 N1 2.101(4) . ? Co1 N1 2.101(4) 2_656 ? Co1 O1 2.129(3) 3_445 ? Co1 O1 2.129(3) 4_646 ? Co1 N4 2.158(4) . ? Co1 N4 2.158(4) 2_656 ? Cu1 O2 1.960(3) 8_466 ? Cu1 O2 1.960(3) 4_646 ? Cu1 N1 1.984(4) . ? Cu1 N1 1.984(4) 5_667 ? O2 C6 1.259(5) . ? O2 Cu1 1.960(3) 4_656 ? N4 C4 1.334(5) . ? N4 C3 1.340(6) . ? N1 N2 1.217(5) . ? C1 C5 1.377(6) . ? C1 C2 1.378(6) . ? C1 C6 1.520(6) . ? N2 N3 1.138(6) . ? C3 C2 1.372(6) . ? C3 H3A 0.9300 . ? C2 H2A 0.9300 . ? C5 C4 1.371(6) . ? C5 H5A 0.9300 . ? C4 H4A 0.9300 . ? 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 C6 O1 Co1 128.0(3) . 3 ? N1 Co1 N1 171.2(2) . 2_656 ? N1 Co1 O1 83.96(13) . 3_445 ? N1 Co1 O1 89.58(13) 2_656 3_445 ? N1 Co1 O1 89.58(13) . 4_646 ? N1 Co1 O1 83.96(13) 2_656 4_646 ? O1 Co1 O1 85.10(17) 3_445 4_646 ? N1 Co1 N4 93.68(15) . . ? N1 Co1 N4 92.20(14) 2_656 . ? O1 Co1 N4 174.25(14) 3_445 . ? O1 Co1 N4 89.65(13) 4_646 . ? N1 Co1 N4 92.20(14) . 2_656 ? N1 Co1 N4 93.68(14) 2_656 2_656 ? O1 Co1 N4 89.65(13) 3_445 2_656 ? O1 Co1 N4 174.25(14) 4_646 2_656 ? N4 Co1 N4 95.7(2) . 2_656 ? O2 Cu1 O2 180.000(1) 8_466 4_646 ? O2 Cu1 N1 88.88(14) 8_466 . ? O2 Cu1 N1 91.12(14) 4_646 . ? O2 Cu1 N1 91.12(14) 8_466 5_667 ? O2 Cu1 N1 88.88(14) 4_646 5_667 ? N1 Cu1 N1 180.000(1) . 5_667 ? C6 O2 Cu1 133.2(3) . 4_656 ? C4 N4 C3 116.3(4) . . ? C4 N4 Co1 116.1(3) . . ? C3 N4 Co1 127.6(3) . . ? N2 N1 Cu1 122.3(3) . . ? N2 N1 Co1 120.1(3) . . ? Cu1 N1 Co1 106.59(17) . . ? C5 C1 C2 117.7(4) . . ? C5 C1 C6 119.9(4) . . ? C2 C1 C6 122.4(4) . . ? N3 N2 N1 178.9(5) . . ? N4 C3 C2 123.8(4) . . ? N4 C3 H3A 118.1 . . ? C2 C3 H3A 118.1 . . ? C3 C2 C1 119.0(4) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? O1 C6 O2 127.7(4) . . ? O1 C6 C1 117.6(4) . . ? O2 C6 C1 114.6(4) . . ? C4 C5 C1 119.5(4) . . ? C4 C5 H5A 120.3 . . ? C1 C5 H5A 120.3 . . ? N4 C4 C5 123.5(4) . . ? N4 C4 H4A 118.2 . . ? C5 C4 H4A 118.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Co1 N4 C4 121.3(4) . . . . ? N1 Co1 N4 C4 -52.2(4) 2_656 . . . ? O1 Co1 N4 C4 55.8(14) 3_445 . . . ? O1 Co1 N4 C4 31.7(4) 4_646 . . . ? N4 Co1 N4 C4 -146.1(4) 2_656 . . . ? N1 Co1 N4 C3 -60.0(4) . . . . ? N1 Co1 N4 C3 126.5(4) 2_656 . . . ? O1 Co1 N4 C3 -125.6(12) 3_445 . . . ? O1 Co1 N4 C3 -149.6(4) 4_646 . . . ? N4 Co1 N4 C3 32.5(4) 2_656 . . . ? O2 Cu1 N1 N2 29.9(4) 8_466 . . . ? O2 Cu1 N1 N2 -150.1(4) 4_646 . . . ? N1 Cu1 N1 N2 101(100) 5_667 . . . ? O2 Cu1 N1 Co1 -113.93(17) 8_466 . . . ? O2 Cu1 N1 Co1 66.07(17) 4_646 . . . ? N1 Cu1 N1 Co1 -43(100) 5_667 . . . ? N1 Co1 N1 N2 -165.5(3) 2_656 . . . ? O1 Co1 N1 N2 -122.8(4) 3_445 . . . ? O1 Co1 N1 N2 152.1(4) 4_646 . . . ? N4 Co1 N1 N2 62.5(4) . . . . ? N4 Co1 N1 N2 -33.4(4) 2_656 . . . ? N1 Co1 N1 Cu1 -20.71(13) 2_656 . . . ? O1 Co1 N1 Cu1 21.99(15) 3_445 . . . ? O1 Co1 N1 Cu1 -63.13(16) 4_646 . . . ? N4 Co1 N1 Cu1 -152.75(17) . . . . ? N4 Co1 N1 Cu1 111.40(17) 2_656 . . . ? Cu1 N1 N2 N3 -142(30) . . . . ? Co1 N1 N2 N3 -3(30) . . . . ? C4 N4 C3 C2 2.1(8) . . . . ? Co1 N4 C3 C2 -176.6(4) . . . . ? N4 C3 C2 C1 1.5(9) . . . . ? C5 C1 C2 C3 -4.7(8) . . . . ? C6 C1 C2 C3 175.5(5) . . . . ? Co1 O1 C6 O2 3.6(7) 3 . . . ? Co1 O1 C6 C1 -177.4(3) 3 . . . ? Cu1 O2 C6 O1 0.4(8) 4_656 . . . ? Cu1 O2 C6 C1 -178.5(3) 4_656 . . . ? C5 C1 C6 O1 -158.3(4) . . . . ? C2 C1 C6 O1 21.6(7) . . . . ? C5 C1 C6 O2 20.8(6) . . . . ? C2 C1 C6 O2 -159.3(5) . . . . ? C2 C1 C5 C4 4.4(7) . . . . ? C6 C1 C5 C4 -175.8(4) . . . . ? C3 N4 C4 C5 -2.4(7) . . . . ? Co1 N4 C4 C5 176.4(4) . . . . ? C1 C5 C4 N4 -0.8(8) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.432 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.083