# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_1 _database_code_depnum_ccdc_archive 'CCDC 901632' #TrackingRef '13991_web_deposit_cif_file_0_Yan-ZhenZheng_1347809673.1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Co N4 O4' _chemical_formula_weight 363.24 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' Co Co 0.3494 0.9721 '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' _symmetry_cell_setting TRICLINIC _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9274(12) _cell_length_b 9.6236(14) _cell_length_c 11.0373(16) _cell_angle_alpha 86.800(2) _cell_angle_beta 74.598(2) _cell_angle_gamma 78.731(2) _cell_volume 796.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour PURPLE _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 374 _exptl_absorpt_coefficient_mu 1.103 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7056 _exptl_absorpt_correction_T_max 0.8015 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 6173 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3074 _reflns_number_gt 2739 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0552P)^2^+0.1212P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3074 _refine_ls_number_parameters 235 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0963 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 0.80250(4) 0.19262(3) -0.11738(3) 0.02874(13) Uani 1 1 d . . . O1 O 0.8325(2) 0.14984(18) 0.05370(16) 0.0401(4) Uani 1 1 d . B . O2 O 0.9943(2) -0.06578(16) 0.22560(16) 0.0355(4) Uani 1 1 d . . . O6 O 0.6357(3) 0.3482(2) 0.08034(19) 0.0531(5) Uani 1 1 d . B . O7 O 1.1250(2) 0.12153(17) 0.19911(19) 0.0462(5) Uani 1 1 d . B . N1 N 0.5606(2) 0.1822(2) -0.13404(18) 0.0320(4) Uani 1 1 d . . . N2 N 0.3152(4) 0.1145(3) -0.1328(3) 0.0592(8) Uani 1 1 d . . . N3 N 0.8666(3) 0.37444(19) -0.20122(19) 0.0343(5) Uani 1 1 d . . . N4 N 0.9009(3) 0.5940(2) -0.2334(2) 0.0473(6) Uani 1 1 d . . . C1 C 0.7010(3) 0.2332(2) 0.2628(2) 0.0364(6) Uani 1 1 d . B . C2 C 0.8199(3) 0.1496(2) 0.3127(2) 0.0332(5) Uani 1 1 d . B . C3 C 0.7950(4) 0.1299(4) 0.4519(3) 0.0603(9) Uani 1 1 d . . . H3A H 0.9061 0.1332 0.4720 0.072 Uiso 1 1 calc R A 1 H3B H 0.7664 0.0370 0.4757 0.072 Uiso 1 1 calc R A 1 C4 C 0.6472(10) 0.2428(12) 0.5288(5) 0.065(2) Uani 0.625(15) 1 d PD B 1 H4A H 0.6169 0.2145 0.6165 0.078 Uiso 0.625(15) 1 calc PR B 1 H4B H 0.6875 0.3324 0.5231 0.078 Uiso 0.625(15) 1 calc PR B 1 C5 C 0.4868(15) 0.2584(16) 0.4771(13) 0.080(3) Uani 0.625(15) 1 d PD B 1 H5A H 0.3873 0.3217 0.5299 0.097 Uiso 0.625(15) 1 calc PR B 1 H5B H 0.4530 0.1669 0.4764 0.097 Uiso 0.625(15) 1 calc PR B 1 C4' C 0.587(2) 0.1682(16) 0.5240(10) 0.074(4) Uani 0.375(15) 1 d PD B 2 H4'A H 0.5233 0.1004 0.5037 0.088 Uiso 0.375(15) 1 calc PR B 2 H4'B H 0.5716 0.1675 0.6143 0.088 Uiso 0.375(15) 1 calc PR B 2 C5' C 0.520(3) 0.3148(14) 0.479(2) 0.072(5) Uani 0.375(15) 1 d PD B 2 H5'A H 0.3977 0.3466 0.5260 0.087 Uiso 0.375(15) 1 calc PR B 2 H5'B H 0.5906 0.3798 0.4964 0.087 Uiso 0.375(15) 1 calc PR B 2 C6 C 0.5311(4) 0.3181(4) 0.3433(3) 0.0587(8) Uani 1 1 d . . . H6A H 0.4337 0.3163 0.3059 0.070 Uiso 1 1 calc R B 1 H6B H 0.5443 0.4158 0.3461 0.070 Uiso 1 1 calc R B 1 C7 C 0.7243(3) 0.2478(3) 0.1247(2) 0.0358(5) Uani 1 1 d . . . C8 C 0.9932(3) 0.0658(2) 0.2374(2) 0.0310(5) Uani 1 1 d . . . C9 C 0.8223(3) 0.5038(3) -0.1545(3) 0.0431(6) Uani 1 1 d . . . H9A H 0.7455 0.5282 -0.0759 0.052 Uiso 1 1 calc R . . C10 C 1.0008(5) 0.5215(3) -0.3370(3) 0.0623(9) Uani 1 1 d . . . H10A H 1.0709 0.5579 -0.4084 0.075 Uiso 1 1 calc R . . C11 C 0.9793(4) 0.3860(3) -0.3169(3) 0.0564(8) Uani 1 1 d . . . H11A H 1.0329 0.3120 -0.3731 0.068 Uiso 1 1 calc R . . C12 C 0.4851(3) 0.0726(3) -0.1371(3) 0.0403(6) Uani 1 1 d . . . H12A H 0.5437 -0.0214 -0.1417 0.048 Uiso 1 1 calc R . . C13 C 0.2773(4) 0.2573(4) -0.1276(3) 0.0622(9) Uani 1 1 d . . . H13A H 0.1674 0.3150 -0.1242 0.075 Uiso 1 1 calc R . . C14 C 0.4283(3) 0.2998(3) -0.1284(3) 0.0431(6) Uani 1 1 d . . . H14A H 0.4418 0.3933 -0.1257 0.052 Uiso 1 1 calc R . . H4 H 0.894(4) 0.669(4) -0.226(3) 0.062(11) Uiso 1 1 d . . . H2 H 0.262(4) 0.070(4) -0.132(3) 0.049(10) Uiso 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 0.02808(19) 0.02273(19) 0.0355(2) -0.00106(12) -0.00873(13) -0.00406(12) O1 0.0489(10) 0.0340(9) 0.0352(9) -0.0046(7) -0.0116(8) -0.0007(8) O2 0.0354(9) 0.0205(8) 0.0473(10) -0.0054(7) -0.0044(7) -0.0043(7) O6 0.0623(13) 0.0404(11) 0.0533(12) 0.0050(9) -0.0212(10) 0.0049(9) O7 0.0363(10) 0.0265(9) 0.0725(13) -0.0049(8) -0.0073(9) -0.0066(7) N1 0.0304(10) 0.0292(10) 0.0362(11) -0.0007(8) -0.0081(8) -0.0057(8) N2 0.0391(15) 0.0535(17) 0.093(2) -0.0195(15) -0.0196(14) -0.0178(13) N3 0.0364(11) 0.0226(10) 0.0436(12) -0.0012(8) -0.0102(9) -0.0048(8) N4 0.0549(15) 0.0217(12) 0.0654(16) -0.0004(11) -0.0133(12) -0.0108(10) C1 0.0343(13) 0.0300(13) 0.0410(14) -0.0051(10) -0.0059(11) -0.0006(10) C2 0.0396(13) 0.0251(12) 0.0331(12) -0.0051(9) -0.0067(10) -0.0042(10) C3 0.065(2) 0.066(2) 0.0370(15) -0.0001(14) -0.0086(14) 0.0107(16) C4 0.069(4) 0.077(5) 0.031(3) -0.006(3) 0.004(3) 0.006(4) C5 0.060(5) 0.079(8) 0.066(5) 0.001(7) 0.027(4) 0.012(5) C4' 0.084(9) 0.076(8) 0.038(5) -0.001(5) 0.013(5) -0.002(7) C5' 0.067(11) 0.063(10) 0.057(7) -0.003(9) 0.011(7) 0.024(8) C6 0.0460(17) 0.060(2) 0.0537(18) -0.0101(15) -0.0045(14) 0.0189(14) C7 0.0375(13) 0.0284(12) 0.0429(14) -0.0005(10) -0.0123(11) -0.0072(10) C8 0.0350(13) 0.0246(12) 0.0333(12) -0.0009(9) -0.0113(10) -0.0018(9) C9 0.0431(15) 0.0270(13) 0.0535(16) -0.0044(11) -0.0028(12) -0.0057(11) C10 0.086(2) 0.0409(17) 0.0530(18) 0.0061(14) 0.0034(17) -0.0261(16) C11 0.078(2) 0.0367(15) 0.0470(17) -0.0066(12) 0.0013(15) -0.0151(14) C12 0.0373(14) 0.0352(14) 0.0503(15) -0.0011(11) -0.0109(12) -0.0116(11) C13 0.0352(15) 0.0567(19) 0.097(3) -0.0201(17) -0.0256(16) 0.0044(13) C14 0.0410(15) 0.0326(14) 0.0562(17) -0.0067(12) -0.0165(13) -0.0012(11) _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 1.9707(16) 2_755 ? Co1 O1 1.9761(17) . ? Co1 N1 1.9967(19) . ? Co1 N3 2.0231(19) . ? O1 C7 1.284(3) . ? O2 C8 1.278(3) . ? O2 Co1 1.9707(16) 2_755 ? O6 C7 1.238(3) . ? O7 C8 1.231(3) . ? N1 C12 1.316(3) . ? N1 C14 1.375(3) . ? N2 C12 1.318(4) . ? N2 C13 1.349(4) . ? N2 H2 0.65(3) . ? N3 C9 1.321(3) . ? N3 C11 1.363(3) . ? N4 C9 1.318(3) . ? N4 C10 1.347(4) . ? N4 H4 0.72(3) . ? C1 C2 1.330(3) . ? C1 C7 1.488(3) . ? C1 C6 1.512(3) . ? C2 C3 1.502(4) . ? C2 C8 1.505(3) . ? C3 C4 1.533(7) . ? C3 C4' 1.606(14) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.506(8) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.531(15) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C4' C5' 1.511(9) . ? C4' H4'A 0.9700 . ? C4' H4'B 0.9700 . ? C5' C6 1.48(2) . ? C5' H5'A 0.9700 . ? C5' H5'B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C9 H9A 0.9300 . ? C10 C11 1.346(4) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.336(4) . ? C13 H13A 0.9300 . ? C14 H14A 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 O2 Co1 O1 103.74(7) 2_755 . ? O2 Co1 N1 116.78(7) 2_755 . ? O1 Co1 N1 113.80(8) . . ? O2 Co1 N3 95.66(7) 2_755 . ? O1 Co1 N3 118.45(8) . . ? N1 Co1 N3 107.44(8) . . ? C7 O1 Co1 106.04(15) . . ? C8 O2 Co1 122.40(15) . 2_755 ? C12 N1 C14 105.7(2) . . ? C12 N1 Co1 130.96(17) . . ? C14 N1 Co1 122.88(16) . . ? C12 N2 C13 108.3(3) . . ? C12 N2 H2 123(3) . . ? C13 N2 H2 129(3) . . ? C9 N3 C11 105.1(2) . . ? C9 N3 Co1 128.64(18) . . ? C11 N3 Co1 126.10(17) . . ? C9 N4 C10 107.7(2) . . ? C9 N4 H4 129(3) . . ? C10 N4 H4 123(3) . . ? C2 C1 C7 122.5(2) . . ? C2 C1 C6 121.9(2) . . ? C7 C1 C6 115.5(2) . . ? C1 C2 C3 123.1(2) . . ? C1 C2 C8 124.3(2) . . ? C3 C2 C8 112.7(2) . . ? C2 C3 C4 112.8(3) . . ? C2 C3 C4' 110.2(5) . . ? C4 C3 C4' 35.0(4) . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? C4' C3 H3A 135.6 . . ? C2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? C4' C3 H3B 77.9 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 108.4(9) . . ? C5 C4 H4A 110.0 . . ? C3 C4 H4A 110.0 . . ? C5 C4 H4B 110.0 . . ? C3 C4 H4B 110.0 . . ? H4A C4 H4B 108.4 . . ? C4 C5 C6 109.4(8) . . ? C4 C5 H5A 109.8 . . ? C6 C5 H5A 109.8 . . ? C4 C5 H5B 109.8 . . ? C6 C5 H5B 109.8 . . ? H5A C5 H5B 108.2 . . ? C5' C4' C3 105.9(15) . . ? C5' C4' H4'A 110.6 . . ? C3 C4' H4'A 110.6 . . ? C5' C4' H4'B 110.6 . . ? C3 C4' H4'B 110.6 . . ? H4'A C4' H4'B 108.7 . . ? C6 C5' C4' 112.1(15) . . ? C6 C5' H5'A 109.2 . . ? C4' C5' H5'A 109.2 . . ? C6 C5' H5'B 109.2 . . ? C4' C5' H5'B 109.2 . . ? H5'A C5' H5'B 107.9 . . ? C5' C6 C1 114.5(8) . . ? C5' C6 C5 25.0(7) . . ? C1 C6 C5 111.2(6) . . ? C5' C6 H6A 126.2 . . ? C1 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? C5' C6 H6B 85.5 . . ? C1 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? O6 C7 O1 121.1(2) . . ? O6 C7 C1 120.8(2) . . ? O1 C7 C1 118.0(2) . . ? O7 C8 O2 124.1(2) . . ? O7 C8 C2 120.6(2) . . ? O2 C8 C2 115.1(2) . . ? N4 C9 N3 111.4(2) . . ? N4 C9 H9A 124.3 . . ? N3 C9 H9A 124.3 . . ? C11 C10 N4 106.5(3) . . ? C11 C10 H10A 126.8 . . ? N4 C10 H10A 126.8 . . ? C10 C11 N3 109.4(3) . . ? C10 C11 H11A 125.3 . . ? N3 C11 H11A 125.3 . . ? N1 C12 N2 110.6(2) . . ? N1 C12 H12A 124.7 . . ? N2 C12 H12A 124.7 . . ? C14 C13 N2 106.7(3) . . ? C14 C13 H13A 126.6 . . ? N2 C13 H13A 126.6 . . ? C13 C14 N1 108.7(2) . . ? C13 C14 H14A 125.6 . . ? N1 C14 H14A 125.6 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4 O7 0.72(3) 2.03(3) 2.745(3) 178(4) 2_765 N2 H2 O1 0.65(3) 2.42(3) 2.996(4) 148(4) 2_655 N2 H2 O2 0.65(3) 2.52(3) 3.021(3) 135(4) 2_655 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.499 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.068 data_2 _database_code_depnum_ccdc_archive 'CCDC 901633' #TrackingRef '13992_web_deposit_cif_file_1_Yan-ZhenZheng_1347809673.2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 Cl2 Co2 N8 O4' _chemical_formula_weight 629.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 13.1008(12) _cell_length_b 9.8330(9) _cell_length_c 19.4152(17) _cell_angle_alpha 90.00 _cell_angle_beta 94.2360(10) _cell_angle_gamma 90.00 _cell_volume 2494.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour dark-purple _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 1.589 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6387 _exptl_absorpt_correction_T_max 0.8446 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7258 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2421 _reflns_number_gt 2246 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0573P)^2^+3.4530P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2421 _refine_ls_number_parameters 171 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0940 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 0.98059(2) 0.07379(3) 0.413438(16) 0.02739(14) Uani 1 1 d . . . Cl1 Cl 0.89362(5) 0.09007(6) 0.51760(3) 0.03488(17) Uani 1 1 d . . . O1 O 1.04756(12) -0.02316(17) 0.32488(8) 0.0292(4) Uani 1 1 d . . . O2 O 0.90908(14) -0.10458(18) 0.36551(10) 0.0371(4) Uani 1 1 d . . . N1 N 0.86857(16) 0.1897(2) 0.35704(11) 0.0344(5) Uani 1 1 d . . . N2 N 0.74100(18) 0.3287(3) 0.33070(13) 0.0463(6) Uani 1 1 d D . . N3 N 1.08326(16) 0.2298(2) 0.42993(11) 0.0340(5) Uani 1 1 d . . . N4 N 1.2213(2) 0.3522(3) 0.42668(16) 0.0561(8) Uani 1 1 d . . . C1 C 0.97997(18) -0.1143(2) 0.32553(11) 0.0271(5) Uani 1 1 d . . . C2 C 0.9873(2) -0.2403(2) 0.28307(13) 0.0350(6) Uani 1 1 d . . . C3 C 0.9778(4) -0.3684(3) 0.32350(18) 0.0660(10) Uani 1 1 d . . . H3A H 0.9065 -0.3823 0.3321 0.079 Uiso 1 1 calc R . . H3B H 1.0164 -0.3589 0.3678 0.079 Uiso 1 1 calc R . . C4 C 1.0165(5) -0.4921(3) 0.28643(19) 0.0909(16) Uani 1 1 d . . . H4A H 1.0907 -0.4936 0.2917 0.109 Uiso 1 1 calc R . . H4B H 0.9917 -0.5738 0.3076 0.109 Uiso 1 1 calc R . . C5 C 0.8534(2) 0.2006(3) 0.28652(15) 0.0504(8) Uani 1 1 d . . . H5A H 0.8917 0.1561 0.2550 0.061 Uiso 1 1 calc R . . C6 C 0.7749(3) 0.2851(4) 0.26997(16) 0.0581(9) Uani 1 1 d . . . H6A H 0.7489 0.3091 0.2258 0.070 Uiso 1 1 calc R . . C7 C 0.7972(2) 0.2678(3) 0.38121(14) 0.0400(6) Uani 1 1 d . . . H7A H 0.7877 0.2787 0.4279 0.048 Uiso 1 1 calc R . . C8 C 1.0713(3) 0.3490(3) 0.46483(19) 0.0559(8) Uani 1 1 d . . . H8A H 1.0135 0.3736 0.4870 0.067 Uiso 1 1 calc R . . C9 C 1.1563(3) 0.4246(3) 0.4620(2) 0.0673(10) Uani 1 1 d . . . H9A H 1.1676 0.5106 0.4810 0.081 Uiso 1 1 calc R . . C10 C 1.1753(2) 0.2366(3) 0.40882(15) 0.0455(7) Uani 1 1 d . . . H10A H 1.2050 0.1680 0.3841 0.055 Uiso 1 1 calc R . . H2 H 0.6888(16) 0.377(3) 0.3320(17) 0.051(9) Uiso 1 1 d D . . H4 H 1.269(3) 0.372(4) 0.415(2) 0.065(13) Uiso 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 0.0244(2) 0.0305(2) 0.0276(2) -0.00302(12) 0.00448(13) -0.00210(12) Cl1 0.0318(3) 0.0451(4) 0.0285(3) 0.0024(2) 0.0073(2) 0.0073(3) O1 0.0287(9) 0.0311(8) 0.0279(8) -0.0013(7) 0.0033(7) -0.0014(7) O2 0.0328(10) 0.0405(10) 0.0395(10) -0.0040(8) 0.0122(8) -0.0033(8) N1 0.0297(11) 0.0388(11) 0.0351(11) -0.0022(9) 0.0055(9) 0.0042(9) N2 0.0322(13) 0.0510(14) 0.0562(15) 0.0023(12) 0.0057(11) 0.0156(11) N3 0.0277(11) 0.0346(11) 0.0400(12) -0.0014(9) 0.0038(9) -0.0034(9) N4 0.0359(15) 0.0633(18) 0.0698(18) 0.0089(14) 0.0085(13) -0.0199(14) C1 0.0294(12) 0.0286(11) 0.0230(11) 0.0018(9) -0.0004(9) 0.0033(9) C2 0.0471(15) 0.0274(12) 0.0305(12) 0.0017(10) 0.0035(11) 0.0003(11) C3 0.118(3) 0.0348(15) 0.0479(18) 0.0030(14) 0.0244(19) -0.0055(18) C4 0.181(5) 0.0306(16) 0.063(2) 0.0070(16) 0.018(3) 0.008(2) C5 0.0463(17) 0.069(2) 0.0368(15) 0.0000(14) 0.0075(12) 0.0203(15) C6 0.0530(19) 0.078(2) 0.0425(16) 0.0102(16) 0.0015(14) 0.0254(17) C7 0.0365(15) 0.0439(15) 0.0400(14) -0.0042(12) 0.0054(11) 0.0072(12) C8 0.0433(18) 0.0468(17) 0.079(2) -0.0203(16) 0.0146(15) -0.0066(14) C9 0.056(2) 0.0493(19) 0.097(3) -0.0162(18) 0.007(2) -0.0204(16) C10 0.0346(15) 0.0516(17) 0.0514(16) -0.0001(13) 0.0111(12) -0.0030(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 N3 2.050(2) . ? Co1 N1 2.101(2) . ? Co1 O2 2.1659(18) . ? Co1 O1 2.2041(16) . ? Co1 Cl1 2.3988(7) . ? Co1 C1 2.516(2) . ? Co1 Cl1 2.6035(7) 5_756 ? Cl1 Co1 2.6035(7) 5_756 ? O1 C1 1.261(3) . ? O2 C1 1.257(3) . ? N1 C7 1.322(3) . ? N1 C5 1.373(4) . ? N2 C7 1.325(4) . ? N2 C6 1.360(4) . ? N2 H2 0.836(10) . ? N3 C10 1.303(3) . ? N3 C8 1.368(4) . ? N4 C10 1.322(4) . ? N4 C9 1.338(5) . ? N4 H4 0.71(4) . ? C1 C2 1.495(3) . ? C2 C2 1.350(5) 2_755 ? C2 C3 1.494(4) . ? C3 C4 1.519(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C4 1.448(8) 2_755 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.343(4) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C9 1.343(5) . ? C8 H8A 0.9300 . ? C9 H9A 0.9300 . ? C10 H10A 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 N3 Co1 N1 95.76(9) . . ? N3 Co1 O2 158.62(8) . . ? N1 Co1 O2 87.25(8) . . ? N3 Co1 O1 98.69(7) . . ? N1 Co1 O1 97.53(7) . . ? O2 Co1 O1 59.94(6) . . ? N3 Co1 Cl1 99.52(6) . . ? N1 Co1 Cl1 92.65(6) . . ? O2 Co1 Cl1 101.48(5) . . ? O1 Co1 Cl1 158.09(5) . . ? N3 Co1 C1 128.70(8) . . ? N1 Co1 C1 94.48(8) . . ? O2 Co1 C1 29.97(7) . . ? O1 Co1 C1 30.06(7) . . ? Cl1 Co1 C1 130.01(6) . . ? N3 Co1 Cl1 89.99(6) . 5_756 ? N1 Co1 Cl1 174.24(6) . 5_756 ? O2 Co1 Cl1 87.54(5) . 5_756 ? O1 Co1 Cl1 81.96(5) . 5_756 ? Cl1 Co1 Cl1 85.97(2) . 5_756 ? C1 Co1 Cl1 82.19(5) . 5_756 ? Co1 Cl1 Co1 94.03(2) . 5_756 ? C1 O1 Co1 88.81(13) . . ? C1 O2 Co1 90.63(14) . . ? C7 N1 C5 104.7(2) . . ? C7 N1 Co1 127.95(18) . . ? C5 N1 Co1 127.31(18) . . ? C7 N2 C6 107.5(2) . . ? C7 N2 H2 130(2) . . ? C6 N2 H2 122(2) . . ? C10 N3 C8 104.7(2) . . ? C10 N3 Co1 126.9(2) . . ? C8 N3 Co1 128.34(19) . . ? C10 N4 C9 107.2(3) . . ? C10 N4 H4 124(3) . . ? C9 N4 H4 129(3) . . ? O2 C1 O1 120.2(2) . . ? O2 C1 C2 118.9(2) . . ? O1 C1 C2 120.6(2) . . ? O2 C1 Co1 59.39(12) . . ? O1 C1 Co1 61.13(12) . . ? C2 C1 Co1 170.38(16) . . ? C2 C2 C3 122.39(16) 2_755 . ? C2 C2 C1 123.71(13) 2_755 . ? C3 C2 C1 113.4(2) . . ? C2 C3 C4 112.5(3) . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C4 C4 C3 112.1(4) 2_755 . ? C4 C4 H4A 109.2 2_755 . ? C3 C4 H4A 109.2 . . ? C4 C4 H4B 109.2 2_755 . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C6 C5 N1 109.8(3) . . ? C6 C5 H5A 125.1 . . ? N1 C5 H5A 125.1 . . ? C5 C6 N2 106.3(3) . . ? C5 C6 H6A 126.8 . . ? N2 C6 H6A 126.8 . . ? N1 C7 N2 111.6(2) . . ? N1 C7 H7A 124.2 . . ? N2 C7 H7A 124.2 . . ? C9 C8 N3 109.2(3) . . ? C9 C8 H8A 125.4 . . ? N3 C8 H8A 125.4 . . ? N4 C9 C8 106.7(3) . . ? N4 C9 H9A 126.6 . . ? C8 C9 H9A 126.6 . . ? N3 C10 N4 112.1(3) . . ? N3 C10 H10A 123.9 . . ? N4 C10 H10A 123.9 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.836(10) 2.089(12) 2.918(3) 171(3) 3_455 N4 H4 O2 0.71(4) 2.15(4) 2.841(3) 167(4) 3 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.358 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.060 data_3 _database_code_depnum_ccdc_archive 'CCDC 901634' #TrackingRef '13993_web_deposit_cif_file_2_Yan-ZhenZheng_1347809673.3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 Co N2 O4' _chemical_formula_weight 295.16 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2601(5) _cell_length_b 7.9312(5) _cell_length_c 9.9686(7) _cell_angle_alpha 84.7960(10) _cell_angle_beta 84.6270(10) _cell_angle_gamma 85.9490(10) _cell_volume 568.01(7) _cell_formula_units_Z 2 _cell_measurement_temperature 288(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour PURPLE _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 302 _exptl_absorpt_coefficient_mu 1.519 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6034 _exptl_absorpt_correction_T_max 0.7120 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 288(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5858 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2206 _reflns_number_gt 2123 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0461P)^2^+0.1433P] 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 REFALL _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2206 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0242 _refine_ls_R_factor_gt 0.0232 _refine_ls_wR_factor_ref 0.0662 _refine_ls_wR_factor_gt 0.0655 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 Co1 Co 0.30052(3) 0.42481(2) 0.45385(2) 0.02161(10) Uani 1 1 d . . . O1 O 0.49702(16) 0.59700(16) 0.38262(12) 0.0278(3) Uani 1 1 d . . . O2 O 0.53072(19) 0.37293(16) 0.26533(14) 0.0353(3) Uani 1 1 d . . . O3 O 0.86722(15) 0.44959(14) 0.40517(11) 0.0236(2) Uani 1 1 d . . . O4 O 1.14273(16) 0.50626(16) 0.30068(12) 0.0286(3) Uani 1 1 d . . . N1 N 0.2639(2) 0.17335(17) 0.48577(15) 0.0266(3) Uani 1 1 d . . . N2 N 0.2739(2) -0.0954(2) 0.55788(19) 0.0368(4) Uani 1 1 d . . . C1 C 0.7002(2) 0.6154(2) 0.18219(16) 0.0230(3) Uani 1 1 d . . . C2 C 0.8816(2) 0.6164(2) 0.19207(16) 0.0226(3) Uani 1 1 d . . . C3 C 0.6005(3) 0.7196(3) 0.0730(2) 0.0338(4) Uani 1 1 d . . . C4 C 0.7192(3) 0.8565(3) 0.0005(2) 0.0369(4) Uani 1 1 d . . . C5 C 0.9139(3) 0.7832(3) -0.0354(2) 0.0359(4) Uani 1 1 d . . . C6 C 1.0084(3) 0.7149(3) 0.0900(2) 0.0315(4) Uani 1 1 d . . . C7 C 0.5723(2) 0.5175(2) 0.28261(17) 0.0242(3) Uani 1 1 d . . . C8 C 0.9690(2) 0.51773(19) 0.30773(16) 0.0213(3) Uani 1 1 d . . . C9 C 0.2038(3) 0.0810(2) 0.3897(2) 0.0335(4) Uani 1 1 d . . . C10 C 0.2095(3) -0.0848(3) 0.4333(2) 0.0388(5) Uani 1 1 d . . . C11 C 0.3055(3) 0.0610(2) 0.58534(19) 0.0314(4) Uani 1 1 d . . . H3A H 0.570(3) 0.646(3) 0.009(2) 0.048(7) Uiso 1 1 d . . . H3B H 0.484(4) 0.774(3) 0.115(2) 0.047(6) Uiso 1 1 d . . . H4A H 0.666(3) 0.905(3) -0.081(2) 0.046(6) Uiso 1 1 d . . . H4B H 0.722(4) 0.952(3) 0.061(3) 0.056(7) Uiso 1 1 d . . . H5A H 0.907(4) 0.692(3) -0.095(3) 0.051(7) Uiso 1 1 d . . . H5B H 0.992(3) 0.867(3) -0.087(2) 0.037(6) Uiso 1 1 d . . . H6A H 1.047(4) 0.801(4) 0.135(3) 0.059(8) Uiso 1 1 d . . . H6B H 1.115(3) 0.645(3) 0.061(2) 0.038(6) Uiso 1 1 d . . . H9 H 0.170(3) 0.128(3) 0.314(3) 0.047(7) Uiso 1 1 d . . . H10 H 0.185(4) -0.176(4) 0.397(3) 0.065(8) Uiso 1 1 d . . . H11 H 0.357(3) 0.083(3) 0.662(2) 0.033(5) Uiso 1 1 d . . . H2N H 0.296(3) -0.181(3) 0.608(2) 0.040(6) Uiso 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 0.01925(14) 0.02119(14) 0.02410(14) 0.00271(9) -0.00333(9) -0.00321(9) O1 0.0203(6) 0.0366(7) 0.0262(6) 0.0020(5) -0.0025(5) -0.0038(5) O2 0.0326(7) 0.0279(6) 0.0466(8) 0.0036(6) -0.0099(6) -0.0099(5) O3 0.0217(6) 0.0243(6) 0.0238(6) 0.0035(4) -0.0026(5) -0.0019(4) O4 0.0182(6) 0.0406(7) 0.0260(6) 0.0037(5) -0.0042(5) -0.0004(5) N1 0.0265(7) 0.0235(7) 0.0293(7) 0.0023(6) -0.0030(6) -0.0034(6) N2 0.0363(9) 0.0224(8) 0.0488(10) 0.0083(7) -0.0009(7) 0.0002(6) C1 0.0249(8) 0.0222(8) 0.0216(8) 0.0021(6) -0.0034(6) -0.0015(6) C2 0.0232(8) 0.0219(7) 0.0222(8) 0.0020(6) -0.0013(6) -0.0026(6) C3 0.0271(10) 0.0400(10) 0.0328(10) 0.0108(8) -0.0086(8) -0.0020(8) C4 0.0382(11) 0.0350(10) 0.0343(10) 0.0132(8) -0.0052(8) 0.0015(8) C5 0.0377(10) 0.0392(10) 0.0280(9) 0.0108(8) 0.0000(8) -0.0047(8) C6 0.0264(9) 0.0359(10) 0.0306(9) 0.0078(8) -0.0018(7) -0.0060(8) C7 0.0166(8) 0.0294(8) 0.0265(8) 0.0064(7) -0.0096(6) -0.0022(6) C8 0.0217(8) 0.0196(7) 0.0231(8) -0.0022(6) -0.0034(6) -0.0011(6) C9 0.0356(10) 0.0316(9) 0.0344(10) -0.0017(8) -0.0096(8) -0.0022(8) C10 0.0380(11) 0.0269(9) 0.0528(12) -0.0080(9) -0.0050(9) -0.0035(8) C11 0.0322(10) 0.0289(9) 0.0322(10) 0.0028(7) -0.0046(8) 0.0000(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N1 2.0231(14) . ? Co1 O4 2.0261(12) 1_455 ? Co1 O3 2.0525(12) 2_666 ? Co1 O1 2.0770(12) . ? Co1 O1 2.2825(12) 2_666 ? O1 C7 1.286(2) . ? O1 Co1 2.2825(12) 2_666 ? O2 C7 1.237(2) . ? O3 C8 1.268(2) . ? O3 Co1 2.0525(12) 2_666 ? O4 C8 1.254(2) . ? O4 Co1 2.0261(12) 1_655 ? N1 C11 1.315(2) . ? N1 C9 1.376(2) . ? N2 C11 1.334(3) . ? N2 C10 1.361(3) . ? C1 C2 1.330(2) . ? C1 C7 1.502(2) . ? C1 C3 1.514(2) . ? C2 C8 1.499(2) . ? C2 C6 1.509(2) . ? C3 C4 1.523(3) . ? C4 C5 1.514(3) . ? C5 C6 1.520(3) . ? C9 C10 1.346(3) . ? 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 Co1 O4 104.43(6) . 1_455 ? N1 Co1 O3 109.11(5) . 2_666 ? O4 Co1 O3 93.80(5) 1_455 2_666 ? N1 Co1 O1 142.36(5) . . ? O4 Co1 O1 90.98(5) 1_455 . ? O3 Co1 O1 103.75(5) 2_666 . ? N1 Co1 O1 90.34(5) . 2_666 ? O4 Co1 O1 165.11(5) 1_455 2_666 ? O3 Co1 O1 82.89(4) 2_666 2_666 ? O1 Co1 O1 75.83(5) . 2_666 ? C7 O1 Co1 97.82(10) . . ? C7 O1 Co1 108.21(10) . 2_666 ? Co1 O1 Co1 104.17(5) . 2_666 ? C8 O3 Co1 126.05(10) . 2_666 ? C8 O4 Co1 126.07(11) . 1_655 ? C11 N1 C9 105.19(15) . . ? C11 N1 Co1 131.61(13) . . ? C9 N1 Co1 122.83(12) . . ? C11 N2 C10 107.92(16) . . ? C2 C1 C7 123.26(14) . . ? C2 C1 C3 123.52(15) . . ? C7 C1 C3 113.16(14) . . ? C1 C2 C8 120.52(14) . . ? C1 C2 C6 122.59(15) . . ? C8 C2 C6 116.89(15) . . ? C1 C3 C4 111.78(16) . . ? C5 C4 C3 110.20(16) . . ? C4 C5 C6 111.67(16) . . ? C2 C6 C5 112.54(16) . . ? O2 C7 O1 121.53(16) . . ? O2 C7 C1 122.01(16) . . ? O1 C7 C1 116.26(14) . . ? O4 C8 O3 123.59(15) . . ? O4 C8 C2 116.70(14) . . ? O3 C8 C2 119.71(14) . . ? C10 C9 N1 109.90(18) . . ? C9 C10 N2 105.79(18) . . ? N1 C11 N2 111.19(18) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N O2 0.82(2) 2.28(2) 3.047(2) 157(2) 2_656 N2 H2N O3 0.82(2) 2.53(2) 3.037(2) 121(2) 2_656 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.309 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.053