# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email buxh@nankai.edu.cn _publ_contact_author_name 'Xian-He Bu' _publ_author_name 'Xian-He Bu' # Attachment '- Crystallographic data-DT-ART-02-2012-030262.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 866059' #TrackingRef '- Crystallographic data-DT-ART-02-2012-030262.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Cl Co2 N5 O5' _chemical_formula_weight 457.56 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' 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 Rhombohedral _symmetry_space_group_name_H-M 'R-3 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 27.518(4) _cell_length_b 27.518(4) _cell_length_c 12.172(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7982(2) _cell_formula_units_Z 18 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22276 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 27.7 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.713 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4104 _exptl_absorpt_coefficient_mu 2.053 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22820 _diffrn_reflns_av_R_equivalents 0.0847 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3123 _reflns_number_gt 2617 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution DirectMethod _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.7.0' _computing_molecular_graphics ? _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^)+(0.0801P)^2^+179.2802P] 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 3123 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0945 _refine_ls_R_factor_gt 0.0767 _refine_ls_wR_factor_ref 0.1929 _refine_ls_wR_factor_gt 0.1840 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _refine_ls_shift/su_max 0.048 _refine_ls_shift/su_mean 0.003 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 0.16463(4) 0.88202(4) 0.90513(7) 0.0171(3) Uani 1 1 d . . . Co2 Co 0.14428(5) 0.89553(4) 0.64462(9) 0.0284(3) Uani 1 1 d . . . O4 O -0.0343(2) 0.7735(2) 1.1205(4) 0.0256(12) Uani 1 1 d . . . O2 O 0.3332(2) 1.0899(2) 0.3080(4) 0.0250(12) Uani 1 1 d . . . O3 O -0.0250(2) 0.7979(2) 1.2974(4) 0.0306(13) Uani 1 1 d . . . O1 O 0.2772(3) 1.0977(2) 0.4300(4) 0.0294(13) Uani 1 1 d . . . N4 N 0.2009(3) 0.9294(3) 0.5061(5) 0.0216(14) Uani 1 1 d . . . N5 N 0.1293(2) 0.8876(2) 1.0558(5) 0.0198(13) Uani 1 1 d . . . C2 C 0.2665(3) 1.0077(3) 0.3990(6) 0.0194(16) Uani 1 1 d . . . C5 C 0.2286(3) 0.9845(3) 0.4851(6) 0.0210(16) Uani 1 1 d . . . H5A H 0.2222 1.0082 0.5297 0.025 Uiso 1 1 calc R . . C11 C 0.0523(3) 0.8481(3) 1.1807(6) 0.0199(15) Uani 1 1 d . . . N1 N 0.1955(2) 0.8731(2) 0.7438(5) 0.0148(12) Uani 1 1 d . . . C4 C 0.2474(4) 0.9164(3) 0.3541(7) 0.0307(19) Uani 1 1 d . . . H4A H 0.2528 0.8918 0.3100 0.037 Uiso 1 1 calc R . . N2 N 0.2463(3) 0.9072(3) 0.7356(6) 0.0343(17) Uani 1 1 d . . . C13 C 0.0760(3) 0.8501(3) 1.0801(6) 0.0210(16) Uani 1 1 d . . . H13A H 0.0541 0.8242 1.0267 0.025 Uiso 1 1 calc R . . C8 C 0.1590(3) 0.9266(3) 1.1310(6) 0.0267(17) Uani 1 1 d . . . H8A H 0.1956 0.9541 1.1141 0.032 Uiso 1 1 calc R . . C1 C 0.2954(3) 1.0709(3) 0.3774(6) 0.0223(16) Uani 1 1 d . . . C10 C 0.0835(3) 0.8877(3) 1.2587(6) 0.0296(19) Uani 1 1 d . . . H10A H 0.0685 0.8877 1.3271 0.035 Uiso 1 1 calc R . . C3 C 0.2765(3) 0.9731(3) 0.3331(6) 0.0257(17) Uani 1 1 d . . . H3A H 0.3022 0.9877 0.2757 0.031 Uiso 1 1 calc R . . C12 C -0.0078(3) 0.8026(3) 1.2007(6) 0.0201(16) Uani 1 1 d . . . C9 C 0.1379(4) 0.9275(4) 1.2319(7) 0.036(2) Uani 1 1 d . . . H9A H 0.1601 0.9549 1.2827 0.043 Uiso 1 1 calc R . . C6 C 0.2103(3) 0.8962(3) 0.4411(6) 0.0241(17) Uani 1 1 d . . . H6A H 0.1912 0.8578 0.4548 0.029 Uiso 1 1 calc R . . N3 N 0.2922(5) 0.9370(4) 0.7312(9) 0.070(3) Uani 1 1 d . . . Cl1 Cl 0.07789(10) 0.86087(10) 0.80350(19) 0.0430(6) Uani 1 1 d . . . O1W O 0.0727(8) 0.9158(5) 0.5570(8) 0.163(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 Co1 0.0160(5) 0.0162(5) 0.0167(5) 0.0014(4) 0.0009(4) 0.0063(4) Co2 0.0382(7) 0.0175(6) 0.0218(6) -0.0011(4) 0.0071(5) 0.0082(5) O4 0.016(3) 0.030(3) 0.022(3) -0.008(2) 0.000(2) 0.005(2) O2 0.029(3) 0.017(3) 0.028(3) 0.009(2) 0.008(2) 0.010(2) O3 0.023(3) 0.038(3) 0.018(3) 0.001(2) 0.002(2) 0.005(3) O1 0.048(4) 0.022(3) 0.024(3) 0.001(2) 0.003(3) 0.022(3) N4 0.024(3) 0.020(3) 0.017(3) 0.005(3) 0.000(3) 0.008(3) N5 0.014(3) 0.019(3) 0.020(3) 0.001(3) 0.000(2) 0.004(3) C2 0.021(4) 0.015(4) 0.018(4) 0.001(3) -0.007(3) 0.006(3) C5 0.022(4) 0.017(4) 0.021(4) -0.004(3) -0.003(3) 0.007(3) C11 0.018(4) 0.023(4) 0.016(4) 0.005(3) 0.002(3) 0.008(3) N1 0.012(3) 0.012(3) 0.017(3) 0.003(2) 0.003(2) 0.003(3) C4 0.041(5) 0.020(4) 0.032(5) 0.001(3) 0.006(4) 0.016(4) N2 0.038(5) 0.036(4) 0.028(4) 0.001(3) 0.007(3) 0.018(4) C13 0.023(4) 0.023(4) 0.016(4) -0.003(3) -0.006(3) 0.010(3) C8 0.019(4) 0.025(4) 0.025(4) 0.003(3) 0.001(3) 0.003(3) C1 0.022(4) 0.023(4) 0.019(4) -0.002(3) -0.006(3) 0.010(3) C10 0.030(4) 0.031(5) 0.021(4) -0.006(3) 0.009(3) 0.010(4) C3 0.027(4) 0.025(4) 0.025(4) 0.002(3) 0.007(3) 0.013(4) C12 0.017(4) 0.020(4) 0.021(4) 0.000(3) 0.000(3) 0.008(3) C9 0.030(5) 0.030(5) 0.033(5) -0.014(4) -0.006(4) 0.004(4) C6 0.029(4) 0.017(4) 0.025(4) 0.002(3) 0.003(3) 0.011(3) N3 0.054(7) 0.064(7) 0.076(7) -0.001(5) 0.007(5) 0.017(6) Cl1 0.0401(13) 0.0498(14) 0.0357(12) 0.0011(10) -0.0009(10) 0.0199(11) O1W 0.36(2) 0.115(9) 0.047(6) -0.007(6) -0.058(9) 0.141(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 Co1 O4 2.055(5) 12_667 ? Co1 O2 2.085(5) 8_665 ? Co1 N5 2.117(6) . ? Co1 N1 2.173(6) 16_566 ? Co1 N1 2.201(6) . ? Co1 Cl1 2.485(3) . ? Co2 O1 2.021(5) 11_456 ? Co2 O3 2.031(5) 12_667 ? Co2 N4 2.165(6) . ? Co2 N1 2.165(6) . ? Co2 Cl1 2.499(3) . ? O4 C12 1.242(9) . ? O4 Co1 2.055(5) 11_457 ? O2 C1 1.235(9) . ? O2 Co1 2.085(5) 6_464 ? O3 C12 1.251(9) . ? O3 Co2 2.031(5) 11_457 ? O1 C1 1.255(9) . ? O1 Co2 2.021(5) 12_666 ? N4 C6 1.329(10) . ? N4 C5 1.337(9) . ? N5 C8 1.334(10) . ? N5 C13 1.338(9) . ? C2 C3 1.374(11) . ? C2 C5 1.388(10) . ? C2 C1 1.529(10) . ? C5 H5A 0.9300 . ? C11 C10 1.374(11) . ? C11 C13 1.376(10) . ? C11 C12 1.513(10) . ? N1 N2 1.239(10) . ? N1 Co1 2.173(6) 16_566 ? C4 C3 1.376(11) . ? C4 C6 1.380(11) . ? C4 H4A 0.9300 . ? N2 N3 1.111(12) . ? C13 H13A 0.9300 . ? C8 C9 1.365(11) . ? C8 H8A 0.9300 . ? C10 C9 1.379(12) . ? C10 H10A 0.9300 . ? C3 H3A 0.9300 . ? C9 H9A 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 O4 Co1 O2 85.1(2) 12_667 8_665 ? O4 Co1 N5 88.6(2) 12_667 . ? O2 Co1 N5 93.0(2) 8_665 . ? O4 Co1 N1 176.5(2) 12_667 16_566 ? O2 Co1 N1 94.6(2) 8_665 16_566 ? N5 Co1 N1 94.9(2) . 16_566 ? O4 Co1 N1 92.4(2) 12_667 . ? O2 Co1 N1 90.9(2) 8_665 . ? N5 Co1 N1 176.0(2) . . ? N1 Co1 N1 84.1(2) 16_566 . ? O4 Co1 Cl1 87.71(16) 12_667 . ? O2 Co1 Cl1 171.44(16) 8_665 . ? N5 Co1 Cl1 91.50(17) . . ? N1 Co1 Cl1 92.26(16) 16_566 . ? N1 Co1 Cl1 84.74(16) . . ? O1 Co2 O3 166.0(2) 11_456 12_667 ? O1 Co2 N4 92.4(2) 11_456 . ? O3 Co2 N4 88.2(2) 12_667 . ? O1 Co2 N1 97.5(2) 11_456 . ? O3 Co2 N1 96.3(2) 12_667 . ? N4 Co2 N1 97.2(2) . . ? O1 Co2 Cl1 89.37(17) 11_456 . ? O3 Co2 Cl1 89.37(17) 12_667 . ? N4 Co2 Cl1 176.79(18) . . ? N1 Co2 Cl1 85.15(16) . . ? C12 O4 Co1 132.9(5) . 11_457 ? C1 O2 Co1 134.7(5) . 6_464 ? C12 O3 Co2 128.7(5) . 11_457 ? C1 O1 Co2 122.6(5) . 12_666 ? C6 N4 C5 118.0(6) . . ? C6 N4 Co2 120.9(5) . . ? C5 N4 Co2 121.1(5) . . ? C8 N5 C13 117.6(6) . . ? C8 N5 Co1 122.2(5) . . ? C13 N5 Co1 120.1(5) . . ? C3 C2 C5 119.2(7) . . ? C3 C2 C1 121.1(7) . . ? C5 C2 C1 119.8(7) . . ? N4 C5 C2 122.5(7) . . ? N4 C5 H5A 118.8 . . ? C2 C5 H5A 118.8 . . ? C10 C11 C13 119.1(7) . . ? C10 C11 C12 122.4(7) . . ? C13 C11 C12 118.4(7) . . ? N2 N1 Co2 112.9(5) . . ? N2 N1 Co1 118.6(5) . 16_566 ? Co2 N1 Co1 118.1(3) . 16_566 ? N2 N1 Co1 109.8(5) . . ? Co2 N1 Co1 97.1(2) . . ? Co1 N1 Co1 95.9(2) 16_566 . ? C3 C4 C6 119.5(7) . . ? C3 C4 H4A 120.3 . . ? C6 C4 H4A 120.3 . . ? N3 N2 N1 177.7(10) . . ? N5 C13 C11 122.8(7) . . ? N5 C13 H13A 118.6 . . ? C11 C13 H13A 118.6 . . ? N5 C8 C9 122.4(7) . . ? N5 C8 H8A 118.8 . . ? C9 C8 H8A 118.8 . . ? O2 C1 O1 126.8(7) . . ? O2 C1 C2 116.6(7) . . ? O1 C1 C2 116.6(7) . . ? C11 C10 C9 117.8(7) . . ? C11 C10 H10A 121.1 . . ? C9 C10 H10A 121.1 . . ? C2 C3 C4 118.2(7) . . ? C2 C3 H3A 120.9 . . ? C4 C3 H3A 120.9 . . ? O4 C12 O3 127.0(7) . . ? O4 C12 C11 117.1(6) . . ? O3 C12 C11 115.9(6) . . ? C8 C9 C10 120.1(7) . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? N4 C6 C4 122.7(7) . . ? N4 C6 H6A 118.7 . . ? C4 C6 H6A 118.7 . . ? Co1 Cl1 Co2 82.10(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Co2 N4 C6 -29.0(6) 11_456 . . . ? O3 Co2 N4 C6 165.0(6) 12_667 . . . ? N1 Co2 N4 C6 68.9(6) . . . . ? Cl1 Co2 N4 C6 -153(3) . . . . ? O1 Co2 N4 C5 152.8(6) 11_456 . . . ? O3 Co2 N4 C5 -13.2(6) 12_667 . . . ? N1 Co2 N4 C5 -109.4(6) . . . . ? Cl1 Co2 N4 C5 29(4) . . . . ? O4 Co1 N5 C8 -52.3(6) 12_667 . . . ? O2 Co1 N5 C8 32.7(6) 8_665 . . . ? N1 Co1 N5 C8 127.6(6) 16_566 . . . ? N1 Co1 N5 C8 -158(3) . . . . ? Cl1 Co1 N5 C8 -140.0(6) . . . . ? O4 Co1 N5 C13 130.2(6) 12_667 . . . ? O2 Co1 N5 C13 -144.7(5) 8_665 . . . ? N1 Co1 N5 C13 -49.8(6) 16_566 . . . ? N1 Co1 N5 C13 25(4) . . . . ? Cl1 Co1 N5 C13 42.6(5) . . . . ? C6 N4 C5 C2 -0.4(11) . . . . ? Co2 N4 C5 C2 177.9(5) . . . . ? C3 C2 C5 N4 -0.4(11) . . . . ? C1 C2 C5 N4 178.1(7) . . . . ? O1 Co2 N1 N2 129.9(5) 11_456 . . . ? O3 Co2 N1 N2 -52.5(5) 12_667 . . . ? N4 Co2 N1 N2 36.5(5) . . . . ? Cl1 Co2 N1 N2 -141.4(5) . . . . ? O1 Co2 N1 Co1 -14.5(3) 11_456 . . 16_566 ? O3 Co2 N1 Co1 163.1(3) 12_667 . . 16_566 ? N4 Co2 N1 Co1 -107.9(3) . . . 16_566 ? Cl1 Co2 N1 Co1 74.3(3) . . . 16_566 ? O1 Co2 N1 Co1 -115.0(2) 11_456 . . . ? O3 Co2 N1 Co1 62.5(2) 12_667 . . . ? N4 Co2 N1 Co1 151.6(2) . . . . ? Cl1 Co2 N1 Co1 -26.30(17) . . . . ? O4 Co1 N1 N2 56.5(5) 12_667 . . . ? O2 Co1 N1 N2 -28.7(5) 8_665 . . . ? N5 Co1 N1 N2 162(3) . . . . ? N1 Co1 N1 N2 -123.2(6) 16_566 . . . ? Cl1 Co1 N1 N2 143.9(5) . . . . ? O4 Co1 N1 Co2 -61.0(2) 12_667 . . . ? O2 Co1 N1 Co2 -146.1(2) 8_665 . . . ? N5 Co1 N1 Co2 44(3) . . . . ? N1 Co1 N1 Co2 119.3(3) 16_566 . . . ? Cl1 Co1 N1 Co2 26.47(17) . . . . ? O4 Co1 N1 Co1 179.7(2) 12_667 . . 16_566 ? O2 Co1 N1 Co1 94.6(2) 8_665 . . 16_566 ? N5 Co1 N1 Co1 -75(3) . . . 16_566 ? N1 Co1 N1 Co1 0.0 16_566 . . 16_566 ? Cl1 Co1 N1 Co1 -92.83(18) . . . 16_566 ? Co2 N1 N2 N3 167(27) . . . . ? Co1 N1 N2 N3 -48(27) 16_566 . . . ? Co1 N1 N2 N3 60(27) . . . . ? C8 N5 C13 C11 -4.1(11) . . . . ? Co1 N5 C13 C11 173.4(6) . . . . ? C10 C11 C13 N5 3.0(12) . . . . ? C12 C11 C13 N5 -178.0(7) . . . . ? C13 N5 C8 C9 3.2(12) . . . . ? Co1 N5 C8 C9 -174.4(7) . . . . ? Co1 O2 C1 O1 -1.6(12) 6_464 . . . ? Co1 O2 C1 C2 176.4(5) 6_464 . . . ? Co2 O1 C1 O2 55.1(10) 12_666 . . . ? Co2 O1 C1 C2 -123.0(6) 12_666 . . . ? C3 C2 C1 O2 -9.4(10) . . . . ? C5 C2 C1 O2 172.1(7) . . . . ? C3 C2 C1 O1 168.8(7) . . . . ? C5 C2 C1 O1 -9.6(10) . . . . ? C13 C11 C10 C9 -0.7(12) . . . . ? C12 C11 C10 C9 -179.7(8) . . . . ? C5 C2 C3 C4 1.2(11) . . . . ? C1 C2 C3 C4 -177.3(7) . . . . ? C6 C4 C3 C2 -1.2(12) . . . . ? Co1 O4 C12 O3 13.8(12) 11_457 . . . ? Co1 O4 C12 C11 -167.6(5) 11_457 . . . ? Co2 O3 C12 O4 -11.3(12) 11_457 . . . ? Co2 O3 C12 C11 170.1(5) 11_457 . . . ? C10 C11 C12 O4 171.1(7) . . . . ? C13 C11 C12 O4 -7.9(10) . . . . ? C10 C11 C12 O3 -10.1(11) . . . . ? C13 C11 C12 O3 170.9(7) . . . . ? N5 C8 C9 C10 -1.1(14) . . . . ? C11 C10 C9 C8 -0.2(13) . . . . ? C5 N4 C6 C4 0.3(11) . . . . ? Co2 N4 C6 C4 -177.9(6) . . . . ? C3 C4 C6 N4 0.5(13) . . . . ? O4 Co1 Cl1 Co2 69.88(16) 12_667 . . . ? O2 Co1 Cl1 Co2 36.8(11) 8_665 . . . ? N5 Co1 Cl1 Co2 158.44(17) . . . . ? N1 Co1 Cl1 Co2 -106.65(16) 16_566 . . . ? N1 Co1 Cl1 Co2 -22.76(16) . . . . ? O1 Co2 Cl1 Co1 120.68(18) 11_456 . . . ? O3 Co2 Cl1 Co1 -73.25(17) 12_667 . . . ? N4 Co2 Cl1 Co1 -115(3) . . . . ? N1 Co2 Cl1 Co1 23.15(16) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.416 _refine_diff_density_min -0.876 _refine_diff_density_rms 0.147 #===end data_2 _database_code_depnum_ccdc_archive 'CCDC 866060' #TrackingRef '- Crystallographic data-DT-ART-02-2012-030262.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 Co N4 O2' _chemical_formula_weight 223.06 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 Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.0825(12) _cell_length_b 10.182(2) _cell_length_c 12.533(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 776.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.909 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864.00 _exptl_absorpt_coefficient_mu 2.177 _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 ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8151 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1777 _reflns_number_gt 1668 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution DirectMethod _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.7.0' _computing_molecular_graphics ? _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^)+(0.0239P)^2^+0.0635P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.029(18) _refine_ls_number_reflns 1777 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0300 _refine_ls_R_factor_gt 0.0264 _refine_ls_wR_factor_ref 0.0522 _refine_ls_wR_factor_gt 0.0513 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 O2 O 0.3169(3) -0.22713(16) 0.34501(12) 0.0318(4) Uani 1 1 d . . . O1 O 0.6085(3) -0.09776(16) 0.37012(12) 0.0291(4) Uani 1 1 d . . . C6 C 0.4585(4) -0.1482(2) 0.31409(17) 0.0219(6) Uani 1 1 d . . . Co1 Co 0.78831(5) 0.18082(3) 0.00829(2) 0.02056(9) Uani 1 1 d . . . N2 N 0.6183(4) 0.3236(2) -0.16888(15) 0.0301(5) Uani 1 1 d . . . C1 C 0.5960(4) -0.0147(2) 0.16086(17) 0.0237(5) Uani 1 1 d . . . H1A H 0.6894 0.0265 0.2091 0.028 Uiso 1 1 calc R . . C5 C 0.4711(4) -0.0391(2) -0.01050(18) 0.0302(5) Uani 1 1 d . . . H5A H 0.4778 -0.0156 -0.0821 0.036 Uiso 1 1 calc R . . N1 N 0.5920(3) 0.3084(2) -0.07294(14) 0.0263(4) Uani 1 1 d . . . C3 C 0.3162(5) -0.1705(3) 0.12594(17) 0.0347(6) Uani 1 1 d . . . H3A H 0.2166 -0.2339 0.1488 0.042 Uiso 1 1 calc R . . N4 N 0.6030(3) 0.02191(19) 0.05787(14) 0.0234(4) Uani 1 1 d . . . C2 C 0.4559(4) -0.1110(2) 0.19787(17) 0.0214(5) Uani 1 1 d . . . N3 N 0.6444(4) 0.3416(3) -0.25730(16) 0.0501(7) Uani 1 1 d . . . C4 C 0.3256(5) -0.1351(3) 0.01952(18) 0.0392(7) Uani 1 1 d . . . H4A H 0.2353 -0.1754 -0.0306 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 O2 0.0415(11) 0.0367(9) 0.0171(7) 0.0063(7) -0.0017(8) -0.0176(9) O1 0.0347(10) 0.0349(10) 0.0177(8) 0.0067(7) -0.0051(8) -0.0071(8) C6 0.0308(14) 0.0188(13) 0.0160(11) 0.0004(9) -0.0023(10) 0.0019(10) Co1 0.02366(15) 0.02546(15) 0.01256(13) 0.00126(13) 0.00043(12) -0.00147(13) N2 0.0254(11) 0.0409(12) 0.0240(10) 0.0041(10) -0.0001(8) 0.0040(12) C1 0.0261(13) 0.0281(13) 0.0170(11) 0.0032(10) -0.0036(9) -0.0030(11) C5 0.0420(14) 0.0353(13) 0.0131(11) 0.0032(11) -0.0032(12) -0.0054(11) N1 0.0248(11) 0.0383(12) 0.0157(9) 0.0045(9) 0.0005(7) 0.0021(10) C3 0.0415(16) 0.0399(14) 0.0228(11) 0.0056(11) -0.0037(11) -0.0182(14) N4 0.0273(11) 0.0285(11) 0.0143(9) 0.0007(8) 0.0016(8) -0.0029(9) C2 0.0255(13) 0.0247(12) 0.0140(10) 0.0029(9) 0.0014(9) 0.0000(10) N3 0.0492(16) 0.0812(19) 0.0201(11) 0.0127(12) 0.0019(10) -0.0043(15) C4 0.0496(18) 0.0496(15) 0.0185(11) 0.0021(10) -0.0090(12) -0.0213(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 O2 C6 1.240(3) . ? O2 Co1 2.1606(16) 3_645 ? O1 C6 1.260(3) . ? O1 Co1 2.0267(15) 2_655 ? C6 C2 1.505(3) . ? Co1 N1 2.020(2) 4 ? Co1 O1 2.0267(15) 2_654 ? Co1 N1 2.037(2) . ? Co1 N4 2.068(2) . ? Co1 O2 2.1606(16) 3_655 ? N2 N3 1.134(3) . ? N2 N1 1.223(2) . ? C1 N4 1.344(3) . ? C1 C2 1.379(3) . ? C1 H1A 0.9300 . ? C5 N4 1.328(3) . ? C5 C4 1.371(3) . ? C5 H5A 0.9300 . ? N1 Co1 2.020(2) 4_455 ? C3 C2 1.379(3) . ? C3 C4 1.383(3) . ? C3 H3A 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 O2 Co1 138.82(15) . 3_645 ? C6 O1 Co1 122.02(15) . 2_655 ? O2 C6 O1 126.3(2) . . ? O2 C6 C2 117.3(2) . . ? O1 C6 C2 116.4(2) . . ? N1 Co1 O1 94.71(8) 4 2_654 ? N1 Co1 N1 134.57(5) 4 . ? O1 Co1 N1 91.19(7) 2_654 . ? N1 Co1 N4 114.87(8) 4 . ? O1 Co1 N4 95.69(7) 2_654 . ? N1 Co1 N4 109.25(9) . . ? N1 Co1 O2 84.60(8) 4 3_655 ? O1 Co1 O2 178.75(7) 2_654 3_655 ? N1 Co1 O2 88.57(7) . 3_655 ? N4 Co1 O2 85.54(7) . 3_655 ? N3 N2 N1 177.9(3) . . ? N4 C1 C2 122.7(2) . . ? N4 C1 H1A 118.7 . . ? C2 C1 H1A 118.7 . . ? N4 C5 C4 123.1(2) . . ? N4 C5 H5A 118.4 . . ? C4 C5 H5A 118.4 . . ? N2 N1 Co1 120.47(16) . 4_455 ? N2 N1 Co1 119.70(17) . . ? Co1 N1 Co1 111.72(8) 4_455 . ? C2 C3 C4 119.3(2) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C5 N4 C1 118.1(2) . . ? C5 N4 Co1 120.09(15) . . ? C1 N4 Co1 121.53(16) . . ? C1 C2 C3 118.2(2) . . ? C1 C2 C6 119.9(2) . . ? C3 C2 C6 121.9(2) . . ? C5 C4 C3 118.5(2) . . ? C5 C4 H4A 120.7 . . ? C3 C4 H4A 120.7 . . ? 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 Co1 O2 C6 O1 4.0(4) 3_645 . . . ? Co1 O2 C6 C2 -177.67(17) 3_645 . . . ? Co1 O1 C6 O2 21.3(3) 2_655 . . . ? Co1 O1 C6 C2 -157.05(15) 2_655 . . . ? N3 N2 N1 Co1 98(8) . . . 4_455 ? N3 N2 N1 Co1 -116(8) . . . . ? N1 Co1 N1 N2 82.60(17) 4 . . . ? O1 Co1 N1 N2 -15.2(2) 2_654 . . . ? N4 Co1 N1 N2 -111.7(2) . . . . ? O2 Co1 N1 N2 163.6(2) 3_655 . . . ? N1 Co1 N1 Co1 -128.57(13) 4 . . 4_455 ? O1 Co1 N1 Co1 133.63(10) 2_654 . . 4_455 ? N4 Co1 N1 Co1 37.18(11) . . . 4_455 ? O2 Co1 N1 Co1 -47.59(10) 3_655 . . 4_455 ? C4 C5 N4 C1 1.5(4) . . . . ? C4 C5 N4 Co1 -172.4(2) . . . . ? C2 C1 N4 C5 -1.0(4) . . . . ? C2 C1 N4 Co1 172.81(19) . . . . ? N1 Co1 N4 C5 -142.84(18) 4 . . . ? O1 Co1 N4 C5 -44.96(19) 2_654 . . . ? N1 Co1 N4 C5 48.3(2) . . . . ? O2 Co1 N4 C5 135.21(19) 3_655 . . . ? N1 Co1 N4 C1 43.5(2) 4 . . . ? O1 Co1 N4 C1 141.36(19) 2_654 . . . ? N1 Co1 N4 C1 -125.38(19) . . . . ? O2 Co1 N4 C1 -38.47(19) 3_655 . . . ? N4 C1 C2 C3 -0.7(4) . . . . ? N4 C1 C2 C6 179.3(2) . . . . ? C4 C3 C2 C1 2.0(4) . . . . ? C4 C3 C2 C6 -178.1(2) . . . . ? O2 C6 C2 C1 174.0(2) . . . . ? O1 C6 C2 C1 -7.5(3) . . . . ? O2 C6 C2 C3 -5.9(4) . . . . ? O1 C6 C2 C3 172.6(2) . . . . ? N4 C5 C4 C3 -0.3(4) . . . . ? C2 C3 C4 C5 -1.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.286 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.056