# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_mm059 _database_code_depnum_ccdc_archive 'CCDC 863671' #TrackingRef 'mm059_new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H8.92 Co N3 O4.38' _chemical_formula_weight 288.04 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 Hexagonal _symmetry_space_group_name_H-M P6(3)mc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-y, -x, z' '-x+y, y, z' 'x, x-y, z' 'y, x, z+1/2' 'x-y, -y, z+1/2' '-x, -x+y, z+1/2' _cell_length_a 15.9295(5) _cell_length_b 15.9295(5) _cell_length_c 19.7200(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4333.5(2) _cell_formula_units_Z 6 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 7387 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 23.18 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 0.598 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9051 _exptl_absorpt_correction_T_max 0.9156 _exptl_absorpt_process_details 'SADABS, Bruker (2003)' _exptl_special_details ; Data collection is performed with three batch runs at phi = 0.00 deg (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg (650 frames). Frame width = 0.30 deg in omega. Data is merged, corrected for decay (if any), and treated with multi-scan absorption corrections (if required). All symmetry-equivalent reflections are merged for centrosymmetric data. Friedel pairs are not merged for noncentrosymmetric data. ; _diffrn_ambient_temperature 200(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26156 _diffrn_reflns_av_R_equivalents 0.0756 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 21.95 _reflns_number_total 1911 _reflns_number_gt 1538 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, Bruker (2009)' _computing_cell_refinement 'APEX II, Bruker (2009)' _computing_data_reduction 'XPREP, Bruker (2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL, Bruker (2004)' _computing_publication_material 'SHELXTL, Bruker (2004)' _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^)+(0.1220P)^2^+1.9342P] 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 0.00(15) _refine_ls_number_reflns 1911 _refine_ls_number_parameters 110 _refine_ls_number_restraints 83 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1749 _refine_ls_wR_factor_gt 0.1492 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.034 _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 Co1 Co 0.47672(7) 0.73836(3) 0.31710(10) 0.0466(4) Uani 1 2 d S . . N1 N 0.6342(4) 1.1802(4) 0.7406(3) 0.0562(15) Uani 1 1 d . . . N2 N 0.5487(3) 1.0974(7) 0.6519(4) 0.060(2) Uani 1 2 d SD . . O1 O 0.4911(4) 0.8394(4) 0.3911(2) 0.0644(13) Uani 1 1 d . . . O2 O 0.3333 0.6667 0.3384(4) 0.045(2) Uani 1 6 d S . . O3 O 0.6241(5) 0.8121(3) 0.2965(3) 0.084(2) Uani 1 2 d S . . H3C H 0.6639 0.8665 0.3194 0.126 Uiso 0.21 1 d PR . . H3D H 0.6484 0.7893 0.2648 0.126 Uiso 0.21 1 d PR . . C1 C 0.6336(5) 1.1324(6) 0.6866(3) 0.0655(19) Uani 1 1 d . . . H1A H 0.6858 1.1232 0.6732 0.079 Uiso 1 1 calc R . . C2 C 0.5212(4) 1.0425(8) 0.5912(5) 0.070(3) Uani 1 2 d SU . . C3 C 0.5698(14) 0.9926(15) 0.5712(10) 0.076(5) Uani 0.50 1 d PDU A 1 H3A H 0.6225 0.9980 0.5972 0.091 Uiso 0.50 1 calc PR A 1 C4 C 0.5400(12) 0.9364(16) 0.5138(7) 0.079(5) Uani 0.50 1 d PDU A 1 H4A H 0.5713 0.9013 0.5010 0.095 Uiso 0.50 1 calc PR A 1 C3' C 0.5887(15) 1.0404(15) 0.5493(8) 0.070(5) Uani 0.50 1 d PDU A 2 H3B H 0.6556 1.0806 0.5591 0.084 Uiso 0.50 1 calc PR A 2 C4' C 0.5610(11) 0.9812(13) 0.4932(9) 0.077(5) Uani 0.50 1 d PDU A 2 H4B H 0.6084 0.9756 0.4674 0.092 Uiso 0.50 1 calc PR A 2 C5 C 0.4649(5) 0.9299(9) 0.4742(5) 0.075(3) Uani 1 2 d SDU . . C6 C 0.4319(4) 0.8637(8) 0.4129(4) 0.064(3) Uani 1 2 d SU . . O4 O 0.8275(6) 0.6549(12) 0.6049(9) 0.139(5) Uiso 0.67 2 d SP . . H4C H 0.8300 0.6197 0.5661 0.208 Uiso 0.33 1 d PR . . H4D H 0.8805 0.7059 0.6244 0.208 Uiso 0.33 1 d PR . . O5 O 0.952(4) 0.154(4) 0.653(3) 0.139(5) Uiso 0.13 1 d P . . H5A H 0.9439 0.1651 0.6067 0.208 Uiso 0.13 1 d PR . . H5B H 1.0089 0.2135 0.6732 0.208 Uiso 0.13 1 d PR . . O6 O 0.678(4) 0.074(4) 0.345(3) 0.139(5) Uiso 0.06 1 d PR . . H7A H 0.6551 0.0671 0.2992 0.208 Uiso 0.06 1 d PR . . H7B H 0.7477 0.0904 0.3452 0.208 Uiso 0.06 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 0.0542(6) 0.0576(5) 0.0268(5) -0.0005(3) -0.0009(7) 0.0271(3) N1 0.069(3) 0.060(3) 0.040(3) -0.008(3) -0.003(3) 0.032(3) N2 0.066(4) 0.073(6) 0.044(4) -0.027(4) -0.014(2) 0.037(3) O1 0.073(3) 0.068(3) 0.045(3) -0.024(2) -0.012(2) 0.030(3) O2 0.049(3) 0.049(3) 0.037(6) 0.000 0.000 0.0246(16) O3 0.082(5) 0.094(4) 0.073(5) 0.0022(16) 0.004(3) 0.041(2) C1 0.071(5) 0.091(5) 0.042(4) -0.013(4) 0.002(3) 0.045(4) C2 0.078(4) 0.078(6) 0.054(5) -0.026(5) -0.013(2) 0.039(3) C3 0.068(10) 0.106(14) 0.062(10) -0.034(9) -0.020(8) 0.050(10) C4 0.085(10) 0.113(14) 0.046(9) -0.031(8) -0.006(7) 0.054(10) C3' 0.074(9) 0.081(11) 0.045(8) -0.016(7) 0.004(7) 0.030(9) C4' 0.076(8) 0.086(13) 0.057(9) -0.025(8) 0.003(7) 0.031(8) C5 0.088(5) 0.083(8) 0.051(6) -0.027(5) -0.013(2) 0.042(4) C6 0.083(6) 0.072(7) 0.035(4) -0.003(4) -0.002(2) 0.036(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 Co1 O2 2.0220(18) . ? Co1 O3 2.074(7) . ? Co1 O1 2.099(5) . ? Co1 O1 2.099(5) 9_565 ? Co1 N1 2.136(5) 6_654 ? Co1 N1 2.136(5) 11_674 ? N1 C1 1.307(9) . ? N1 N1 1.406(11) 8 ? N1 Co1 2.136(5) 5_565 ? N2 C1 1.362(8) . ? N2 C1 1.362(8) 8 ? N2 C2 1.417(12) . ? O1 C6 1.261(7) . ? O2 Co1 2.0221(18) 2_665 ? O2 Co1 2.0221(18) 3_565 ? C2 C3' 1.368(17) 8 ? C2 C3' 1.368(17) . ? C2 C3 1.414(17) . ? C2 C3 1.414(17) 8 ? C3 C4 1.372(17) . ? C4 C5 1.389(14) . ? C3' C4' 1.375(17) . ? C4' C5 1.378(14) . ? C5 C4' 1.378(14) 8 ? C5 C4 1.389(14) 8 ? C5 C6 1.514(16) . ? C6 O1 1.261(7) 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 Co1 O3 179.3(3) . . ? O2 Co1 O1 87.0(2) . . ? O3 Co1 O1 92.47(19) . . ? O2 Co1 O1 87.0(2) . 9_565 ? O3 Co1 O1 92.47(19) . 9_565 ? O1 Co1 O1 90.9(3) . 9_565 ? O2 Co1 N1 90.2(2) . 6_654 ? O3 Co1 N1 90.3(2) . 6_654 ? O1 Co1 N1 176.7(2) . 6_654 ? O1 Co1 N1 90.68(17) 9_565 6_654 ? O2 Co1 N1 90.2(2) . 11_674 ? O3 Co1 N1 90.3(2) . 11_674 ? O1 Co1 N1 90.68(17) . 11_674 ? O1 Co1 N1 176.7(2) 9_565 11_674 ? N1 Co1 N1 87.6(3) 6_654 11_674 ? C1 N1 N1 106.5(4) . 8 ? C1 N1 Co1 135.0(5) . 5_565 ? N1 N1 Co1 118.23(15) 8 5_565 ? C1 N2 C1 104.2(7) . 8 ? C1 N2 C2 127.9(4) . . ? C1 N2 C2 127.9(4) 8 . ? C6 O1 Co1 131.4(5) . . ? Co1 O2 Co1 115.82(15) . 2_665 ? Co1 O2 Co1 115.82(15) . 3_565 ? Co1 O2 Co1 115.82(15) 2_665 3_565 ? N1 C1 N2 111.3(6) . . ? C3' C2 C3' 105.7(17) 8 . ? C3' C2 C3 118.8(11) 8 . ? C3' C2 C3 33.0(10) . . ? C3' C2 C3 33.0(10) 8 8 ? C3' C2 C3 118.8(11) . 8 ? C3 C2 C3 111.8(16) . 8 ? C3' C2 N2 121.4(9) 8 . ? C3' C2 N2 121.4(9) . . ? C3 C2 N2 119.7(9) . . ? C3 C2 N2 119.7(8) 8 . ? C4 C3 C2 119.3(17) . . ? C3 C4 C5 121.1(17) . . ? C2 C3' C4' 121.0(18) . . ? C5 C4' C3' 120.4(17) . . ? C4' C5 C4' 108.9(18) . 8 ? C4' C5 C4 118.9(11) . 8 ? C4' C5 C4 31.0(10) 8 8 ? C4' C5 C4 31.0(10) . . ? C4' C5 C4 118.9(11) 8 . ? C4 C5 C4 111.0(16) 8 . ? C4' C5 C6 121.8(8) . . ? C4' C5 C6 121.8(8) 8 . ? C4 C5 C6 119.2(9) 8 . ? C4 C5 C6 119.2(9) . . ? O1 C6 O1 128.8(9) 8 . ? O1 C6 C5 115.6(5) 8 . ? O1 C6 C5 115.6(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Co1 O1 C6 -26.5(7) . . . . ? O3 Co1 O1 C6 154.0(7) . . . . ? O1 Co1 O1 C6 -113.5(7) 9_565 . . . ? N1 Co1 O1 C6 5(5) 6_654 . . . ? N1 Co1 O1 C6 63.6(7) 11_674 . . . ? O3 Co1 O2 Co1 109.8(5) . . . 2_665 ? O1 Co1 O2 Co1 64.2(4) . . . 2_665 ? O1 Co1 O2 Co1 155.3(3) 9_565 . . 2_665 ? N1 Co1 O2 Co1 -114.1(3) 6_654 . . 2_665 ? N1 Co1 O2 Co1 -26.4(4) 11_674 . . 2_665 ? O3 Co1 O2 Co1 -109.8(5) . . . 3_565 ? O1 Co1 O2 Co1 -155.3(4) . . . 3_565 ? O1 Co1 O2 Co1 -64.2(4) 9_565 . . 3_565 ? N1 Co1 O2 Co1 26.4(4) 6_654 . . 3_565 ? N1 Co1 O2 Co1 114.1(3) 11_674 . . 3_565 ? N1 N1 C1 N2 -2.3(7) 8 . . . ? Co1 N1 C1 N2 -176.2(6) 5_565 . . . ? C1 N2 C1 N1 3.6(11) 8 . . . ? C2 N2 C1 N1 179.9(10) . . . . ? C1 N2 C2 C3' -156.7(13) . . . 8 ? C1 N2 C2 C3' 18.7(19) 8 . . 8 ? C1 N2 C2 C3' -18.7(19) . . . . ? C1 N2 C2 C3' 156.7(13) 8 . . . ? C1 N2 C2 C3 20(2) . . . . ? C1 N2 C2 C3 -164.7(14) 8 . . . ? C1 N2 C2 C3 164.7(14) . . . 8 ? C1 N2 C2 C3 -20(2) 8 . . 8 ? C3' C2 C3 C4 -6(3) 8 . . . ? C3' C2 C3 C4 -80(3) . . . . ? C3 C2 C3 C4 30(3) 8 . . . ? N2 C2 C3 C4 177.3(17) . . . . ? C2 C3 C4 C5 2(3) . . . . ? C3' C2 C3' C4' -41(3) 8 . . . ? C3 C2 C3' C4' 78(3) . . . . ? C3 C2 C3' C4' -8(3) 8 . . . ? N2 C2 C3' C4' 174.9(16) . . . . ? C2 C3' C4' C5 7(3) . . . . ? C3' C4' C5 C4' 30(3) . . . 8 ? C3' C4' C5 C4 -2(3) . . . 8 ? C3' C4' C5 C4 -85(3) . . . . ? C3' C4' C5 C6 -179.8(16) . . . . ? C3 C4 C5 C4' 78(3) . . . . ? C3 C4 C5 C4' 0(3) . . . 8 ? C3 C4 C5 C4 -33(3) . . . 8 ? C3 C4 C5 C6 -177.5(18) . . . . ? Co1 O1 C6 O1 -7.4(16) . . . 8 ? Co1 O1 C6 C5 171.6(7) . . . . ? C4' C5 C6 O1 -163.6(14) . . . 8 ? C4' C5 C6 O1 -17.2(19) 8 . . 8 ? C4 C5 C6 O1 18.8(17) 8 . . 8 ? C4 C5 C6 O1 160.4(13) . . . 8 ? C4' C5 C6 O1 17.2(18) . . . . ? C4' C5 C6 O1 163.6(14) 8 . . . ? C4 C5 C6 O1 -160.4(13) 8 . . . ? C4 C5 C6 O1 -18.8(17) . . . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 21.95 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.512 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.061 data_mm072 _database_code_depnum_ccdc_archive 'CCDC 863672' #TrackingRef 'web_deposit_cif_file_1_TomokoAharen_1326924894.mm072.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H6 Co N6 O2' _chemical_formula_weight 289.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 14.5002(3) _cell_length_b 7.1357(2) _cell_length_c 11.3090(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.9390(10) _cell_angle_gamma 90.00 _cell_volume 1043.16(5) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9941 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 28.23 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.841 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 1.649 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8267 _exptl_absorpt_correction_T_max 0.8394 _exptl_absorpt_process_details 'SADABS, Bruker (2003)' _exptl_special_details ; Data collection is performed with three batch runs at phi = 0.00 deg (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg (650 frames). Frame width = 0.30 deg in omega. Data is merged, corrected for decay (if any), and treated with multi-scan absorption corrections (if required). All symmetry-equivalent reflections are merged for centrosymmetric data. Friedel pairs are not merged for noncentrosymmetric data. ; _diffrn_ambient_temperature 200(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13736 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0076 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 28.28 _reflns_number_total 1369 _reflns_number_gt 1322 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, Bruker (2009)' _computing_cell_refinement 'APEX II, Bruker (2009)' _computing_data_reduction 'XPREP, Bruker (2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL, Bruker (2004)' _computing_publication_material 'SHELXTL, Bruker (2004)' _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^)+(0.0391P)^2^+0.4138P] 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 1369 _refine_ls_number_parameters 94 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0174 _refine_ls_R_factor_gt 0.0168 _refine_ls_wR_factor_ref 0.0532 _refine_ls_wR_factor_gt 0.0525 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.2500 0.2500 0.5000 0.01339(8) Uani 1 2 d S . . N1 N 0.33369(7) 0.09670(12) 0.41552(8) 0.01900(17) Uani 1 1 d . . . N2 N 0.37042(9) 0.0000 0.25750(11) 0.0171(2) Uani 1 2 d S . . N3 N 0.15996(9) 0.0000 0.47067(11) 0.0175(2) Uani 1 2 d S . . N4 N 0.07055(9) 0.0000 0.39054(12) 0.0202(2) Uani 1 2 d S . . N5 N -0.01528(11) 0.0000 0.31376(17) 0.0350(3) Uani 1 2 d S . . O1 O 0.34550(6) 0.15771(10) -0.31083(6) 0.02098(16) Uani 1 1 d . . . C1 C 0.35568(8) 0.15101(14) 0.32098(10) 0.0214(2) Uani 1 1 d . . . H1A H 0.3607 0.2780 0.2994 0.026 Uiso 1 1 calc R . . C2 C 0.37785(10) 0.0000 0.13488(12) 0.0162(2) Uani 1 2 d S . . C3 C 0.37814(8) 0.16934(14) 0.07449(9) 0.0225(2) Uani 1 1 d . . . H3A H 0.3815 0.2845 0.1184 0.027 Uiso 1 1 calc R . . C4 C 0.37339(8) 0.16789(14) -0.05124(9) 0.0209(2) Uani 1 1 d . . . H4A H 0.3734 0.2831 -0.0933 0.025 Uiso 1 1 calc R . . C5 C 0.36858(10) 0.0000 -0.11597(12) 0.0158(2) Uani 1 2 d S . . C6 C 0.35281(10) 0.0000 -0.25783(12) 0.0161(2) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.02065(12) 0.01070(12) 0.01080(11) -0.00048(5) 0.00885(8) -0.00081(5) N1 0.0300(4) 0.0140(4) 0.0188(4) -0.0012(3) 0.0162(3) -0.0026(3) N2 0.0242(5) 0.0166(5) 0.0148(5) 0.000 0.0126(4) 0.000 N3 0.0208(5) 0.0124(5) 0.0190(5) 0.000 0.0087(4) 0.000 N4 0.0248(6) 0.0121(5) 0.0261(6) 0.000 0.0135(5) 0.000 N5 0.0234(6) 0.0240(7) 0.0472(8) 0.000 0.0071(6) 0.000 O1 0.0306(3) 0.0183(4) 0.0127(3) 0.0011(2) 0.0086(3) -0.0022(3) C1 0.0347(5) 0.0158(5) 0.0216(4) -0.0027(3) 0.0196(4) -0.0037(4) C2 0.0197(6) 0.0191(6) 0.0129(5) 0.000 0.0100(5) 0.000 C3 0.0368(5) 0.0172(5) 0.0181(4) -0.0029(3) 0.0164(4) -0.0030(4) C4 0.0325(5) 0.0170(5) 0.0164(4) 0.0007(3) 0.0138(4) -0.0021(4) C5 0.0177(5) 0.0190(6) 0.0114(5) 0.000 0.0073(4) 0.000 C6 0.0186(6) 0.0191(6) 0.0111(5) 0.000 0.0071(4) 0.000 _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 O1 2.0601(7) 7 ? Co1 O1 2.0601(7) 1_556 ? Co1 N3 2.1458(6) . ? Co1 N3 2.1458(6) 7_556 ? Co1 N1 2.1523(8) 7_556 ? Co1 N1 2.1523(8) . ? N1 C1 1.3053(12) . ? N1 N1 1.3801(17) 6 ? N2 C1 1.3642(12) 6 ? N2 C1 1.3642(12) . ? N2 C2 1.4388(16) . ? N3 N4 1.1990(17) . ? N3 Co1 2.1458(6) 4_546 ? N4 N5 1.1505(19) . ? O1 C6 1.2567(9) . ? O1 Co1 2.0600(7) 1_554 ? C2 C3 1.3889(11) . ? C2 C3 1.3890(11) 6 ? C3 C4 1.3921(12) . ? C4 C5 1.3892(11) . ? C5 C4 1.3892(11) 6 ? C5 C6 1.5144(17) . ? C6 O1 1.2567(9) 6 ? 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 O1 Co1 O1 180.0 7 1_556 ? O1 Co1 N3 91.70(4) 7 . ? O1 Co1 N3 88.30(4) 1_556 . ? O1 Co1 N3 88.30(4) 7 7_556 ? O1 Co1 N3 91.70(4) 1_556 7_556 ? N3 Co1 N3 180.0 . 7_556 ? O1 Co1 N1 92.84(3) 7 7_556 ? O1 Co1 N1 87.16(3) 1_556 7_556 ? N3 Co1 N1 93.74(4) . 7_556 ? N3 Co1 N1 86.26(4) 7_556 7_556 ? O1 Co1 N1 87.16(3) 7 . ? O1 Co1 N1 92.84(3) 1_556 . ? N3 Co1 N1 86.26(4) . . ? N3 Co1 N1 93.74(4) 7_556 . ? N1 Co1 N1 180.0 7_556 . ? C1 N1 N1 107.27(6) . 6 ? C1 N1 Co1 127.50(7) . . ? N1 N1 Co1 120.55(2) 6 . ? C1 N2 C1 104.34(11) 6 . ? C1 N2 C2 127.24(6) 6 . ? C1 N2 C2 127.24(6) . . ? N4 N3 Co1 119.39(4) . . ? N4 N3 Co1 119.39(4) . 4_546 ? Co1 N3 Co1 112.48(5) . 4_546 ? N5 N4 N3 179.93(16) . . ? C6 O1 Co1 130.80(7) . 1_554 ? N1 C1 N2 110.56(9) . . ? C3 C2 C3 120.91(12) . 6 ? C3 C2 N2 119.48(6) . . ? C3 C2 N2 119.48(6) 6 . ? C2 C3 C4 119.08(9) . . ? C5 C4 C3 120.80(9) . . ? C4 C5 C4 119.18(11) 6 . ? C4 C5 C6 120.38(6) 6 . ? C4 C5 C6 120.38(6) . . ? O1 C6 O1 127.13(11) 6 . ? O1 C6 C5 116.42(6) 6 . ? O1 C6 C5 116.42(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 O1 Co1 N1 C1 38.90(9) 7 . . . ? O1 Co1 N1 C1 -141.10(9) 1_556 . . . ? N3 Co1 N1 C1 130.79(9) . . . . ? N3 Co1 N1 C1 -49.21(9) 7_556 . . . ? N1 Co1 N1 C1 -91(20) 7_556 . . . ? O1 Co1 N1 N1 -113.64(2) 7 . . 6 ? O1 Co1 N1 N1 66.36(2) 1_556 . . 6 ? N3 Co1 N1 N1 -21.75(3) . . . 6 ? N3 Co1 N1 N1 158.25(3) 7_556 . . 6 ? N1 Co1 N1 N1 116(20) 7_556 . . 6 ? O1 Co1 N3 N4 -25.31(10) 7 . . . ? O1 Co1 N3 N4 154.69(10) 1_556 . . . ? N3 Co1 N3 N4 161(9) 7_556 . . . ? N1 Co1 N3 N4 67.65(10) 7_556 . . . ? N1 Co1 N3 N4 -112.35(10) . . . . ? O1 Co1 N3 Co1 122.09(5) 7 . . 4_546 ? O1 Co1 N3 Co1 -57.91(5) 1_556 . . 4_546 ? N3 Co1 N3 Co1 -52(9) 7_556 . . 4_546 ? N1 Co1 N3 Co1 -144.95(5) 7_556 . . 4_546 ? N1 Co1 N3 Co1 35.05(5) . . . 4_546 ? Co1 N3 N4 N5 -107(100) . . . . ? Co1 N3 N4 N5 107(100) 4_546 . . . ? N1 N1 C1 N2 0.01(10) 6 . . . ? Co1 N1 C1 N2 -155.41(8) . . . . ? C1 N2 C1 N1 -0.02(15) 6 . . . ? C2 N2 C1 N1 168.23(11) . . . . ? C1 N2 C2 C3 170.83(11) 6 . . . ? C1 N2 C2 C3 5.18(19) . . . . ? C1 N2 C2 C3 -5.18(19) 6 . . 6 ? C1 N2 C2 C3 -170.84(11) . . . 6 ? C3 C2 C3 C4 3.3(2) 6 . . . ? N2 C2 C3 C4 -172.71(11) . . . . ? C2 C3 C4 C5 -0.10(17) . . . . ? C3 C4 C5 C4 -3.0(2) . . . 6 ? C3 C4 C5 C6 173.95(11) . . . . ? Co1 O1 C6 O1 38.0(2) 1_554 . . 6 ? Co1 O1 C6 C5 -139.73(9) 1_554 . . . ? C4 C5 C6 O1 -0.57(18) 6 . . 6 ? C4 C5 C6 O1 -177.45(11) . . . 6 ? C4 C5 C6 O1 177.45(11) 6 . . . ? C4 C5 C6 O1 0.57(18) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.398 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.048