# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Wei-Yin Sun' 'Zhengshuai Bai' 'Man-Sheng Chen' 'Shui-Sheng Chen' 'Taka-aki Okamura' 'Zhi Su' 'Norikazu Ueyama' _publ_contact_author_name 'Wei-Yin Sun' _publ_contact_author_email SUNWY@NJU.EDU.CN _publ_section_title ; Metal-organic frameworks with pyridyl- and carboxylate-containing ligand: syntheses, structures and properties ; # Attachment 'sunwy-cec.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 751967' _audit_creation_date 2008-05-18 _audit_creation_method SHELXL-97 _publ_section_references ; Rigaku Americas and Rigaku Corporation. (2007). CrystalStructure (Version 3.8). Single Crystal Structure Analysis Software. Rigaku Americas, 9009 TX, USA 77381-5209. Rigaku, Tokyo 196-8666, Japan. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M., Polidori, G., and Camalli, M. (1994) J. Appl. Cryst., 27, 435. SIR92 Sheldrick, G.M. (1997). SHELXL97. University of Gottingen, Germany. ; _chemical_name_systematic ; Mn(M4)(dmf)]-1/2(DMF) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18.50 H18.50 Mn N3.50 O6.50' _chemical_formula_sum 'C18.50 H18.50 Mn N3.50 O6.50' _chemical_formula_weight 448.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Mn Mn 0.3368 0.7283 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_Int_Tables_number 60 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x, -y, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y, -z-1/2' 'x-1/2, y-1/2, -z-1/2' _cell_length_a 18.733(2) _cell_length_b 10.2319(14) _cell_length_c 20.283(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3887.6(9) _cell_formula_units_Z 8 _cell_measurement_temperature 200 _cell_measurement_reflns_used 14389 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description column _exptl_crystal_colour light-brown _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1848 _exptl_absorpt_coefficient_mu 0.725 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9310 _exptl_absorpt_correction_T_max 0.9310 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 33949 _diffrn_reflns_av_R_equivalents 0.0950 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4456 _reflns_number_gt 3237 _reflns_threshold_expression I>2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0447P)^2^+2.8623P] 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 4456 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0731 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1091 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.550307(19) 0.33685(3) 0.448934(18) 0.02172(12) Uani 1 1 d . . . O1 O 0.22573(12) 0.4531(3) 0.27872(12) 0.0759(9) Uani 1 1 d . . . O2 O 0.63085(12) 0.2847(2) 0.52593(11) 0.0457(5) Uani 1 1 d . . . O4 O 0.5000 0.0127(5) 0.2500 0.1049(16) Uani 1 2 d S . . O31 O 0.11814(9) 0.70638(16) 0.11916(9) 0.0273(4) Uani 1 1 d . . . O32 O 0.03333(9) 0.61860(16) 0.05867(9) 0.0281(4) Uani 1 1 d . . . O51 O 0.10354(10) 0.01202(17) 0.07422(10) 0.0350(5) Uani 1 1 d . . . O52 O 0.02433(10) 0.13957(18) 0.02535(9) 0.0359(5) Uani 1 1 d . . . N1 N 0.26829(11) 0.3232(2) 0.19679(11) 0.0286(5) Uani 1 1 d . . . H1 H 0.3036 0.2734 0.1832 0.034 Uiso 1 1 calc R . . N2 N 0.67409(14) 0.0814(3) 0.54813(13) 0.0448(6) Uani 1 1 d . . . N4 N 0.5000 -0.2027(6) 0.2500 0.107(2) Uani 1 2 d S . . N11 N 0.46347(11) 0.3611(2) 0.37204(11) 0.0291(5) Uani 1 1 d . . . C1 C 0.20586(12) 0.3361(2) 0.15706(12) 0.0255(5) Uani 1 1 d . . . C2 C 0.17671(13) 0.4592(2) 0.14632(12) 0.0251(5) Uani 1 1 d . . . H2 H 0.1981 0.5339 0.1659 0.030 Uiso 1 1 calc R . . C3 C 0.11670(12) 0.4735(2) 0.10719(12) 0.0224(5) Uani 1 1 d . . . C4 C 0.08592(13) 0.3642(2) 0.07823(12) 0.0223(5) Uani 1 1 d . . . H3 H 0.0453 0.3740 0.0507 0.027 Uiso 1 1 calc R . . C5 C 0.11409(13) 0.2413(2) 0.08928(12) 0.0228(5) Uani 1 1 d . . . C6 C 0.17437(13) 0.2268(2) 0.12871(12) 0.0248(5) Uani 1 1 d . . . H4 H 0.1939 0.1424 0.1362 0.030 Uiso 1 1 calc R . . C11 C 0.27385(15) 0.3872(3) 0.25546(14) 0.0401(7) Uani 1 1 d . . . C12 C 0.45070(15) 0.2722(3) 0.32542(14) 0.0393(7) Uani 1 1 d . . . H5 H 0.4841 0.2032 0.3198 0.047 Uiso 1 1 calc R . . C13 C 0.39140(15) 0.2754(3) 0.28482(14) 0.0404(7) Uani 1 1 d . . . H6 H 0.3842 0.2095 0.2525 0.048 Uiso 1 1 calc R . . C14 C 0.34309(14) 0.3753(3) 0.29210(13) 0.0332(6) Uani 1 1 d . . . C15 C 0.35694(16) 0.4695(3) 0.33923(16) 0.0468(8) Uani 1 1 d . . . H7 H 0.3252 0.5409 0.3451 0.056 Uiso 1 1 calc R . . C16 C 0.41732(16) 0.4586(3) 0.37757(15) 0.0411(7) Uani 1 1 d . . . H8 H 0.4263 0.5243 0.4096 0.049 Uiso 1 1 calc R . . C21 C 0.6235(2) 0.1705(4) 0.55008(18) 0.0380(11) Uani 0.792(7) 1 d P . . H9 H 0.5794 0.1487 0.5704 0.046 Uiso 0.792(7) 1 calc PR . . C21B C 0.6818(10) 0.2179(18) 0.5158(8) 0.056(5) Uani 0.208(7) 1 d P . . H9B H 0.7222 0.2449 0.4910 0.067 Uiso 0.208(7) 1 calc PR . . C22 C 0.7410(2) 0.1044(6) 0.5184(3) 0.0629(15) Uani 0.792(7) 1 d P . . H10 H 0.7362 0.1728 0.4849 0.076 Uiso 0.792(7) 1 calc PR . . H11 H 0.7581 0.0238 0.4977 0.076 Uiso 0.792(7) 1 calc PR . . H12 H 0.7753 0.1325 0.5521 0.076 Uiso 0.792(7) 1 calc PR . . C22B C 0.6249(14) 0.038(2) 0.5805(10) 0.082(8) Uani 0.208(7) 1 d P . . H10B H 0.5855 0.1005 0.5811 0.098 Uiso 0.208(7) 1 calc PR . . H11B H 0.6411 0.0213 0.6258 0.098 Uiso 0.208(7) 1 calc PR . . H12B H 0.6086 -0.0447 0.5609 0.098 Uiso 0.208(7) 1 calc PR . . C23 C 0.6595(3) -0.0493(5) 0.5782(2) 0.0572(14) Uani 0.792(7) 1 d P . . H13 H 0.6092 -0.0541 0.5915 0.069 Uiso 0.792(7) 1 calc PR . . H14 H 0.6900 -0.0614 0.6170 0.069 Uiso 0.792(7) 1 calc PR . . H15 H 0.6696 -0.1180 0.5459 0.069 Uiso 0.792(7) 1 calc PR . . C23B C 0.7377(14) -0.008(3) 0.5252(14) 0.105(10) Uani 0.208(7) 1 d P . . H13B H 0.7334 -0.0940 0.5460 0.126 Uiso 0.208(7) 1 calc PR . . H14B H 0.7830 0.0324 0.5382 0.126 Uiso 0.208(7) 1 calc PR . . H15B H 0.7362 -0.0176 0.4771 0.126 Uiso 0.208(7) 1 calc PR . . C31 C 0.08722(13) 0.6075(2) 0.09490(12) 0.0233(5) Uani 1 1 d . . . C41 C 0.4637(4) -0.0808(7) 0.2689(5) 0.069(2) Uani 0.50 1 d P . . H16 H 0.4196 -0.0749 0.2919 0.082 Uiso 0.50 1 calc PR . . C42 C 0.5586(6) -0.2076(12) 0.2196(5) 0.085(3) Uani 0.50 1 d P . . H17 H 0.5792 -0.1197 0.2168 0.102 Uiso 0.50 1 calc PR . . H18 H 0.5507 -0.2417 0.1750 0.102 Uiso 0.50 1 calc PR . . H19 H 0.5916 -0.2653 0.2433 0.102 Uiso 0.50 1 calc PR . . C43 C 0.4607(9) -0.3161(15) 0.2645(11) 0.215(13) Uani 0.50 1 d P . . H20 H 0.4756 -0.3505 0.3074 0.258 Uiso 0.50 1 calc PR . . H21 H 0.4693 -0.3819 0.2303 0.258 Uiso 0.50 1 calc PR . . H22 H 0.4097 -0.2948 0.2658 0.258 Uiso 0.50 1 calc PR . . C51 C 0.07842(13) 0.1228(2) 0.06030(12) 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 Mn1 0.0231(2) 0.01786(19) 0.0242(2) -0.00006(15) -0.00055(16) 0.00050(14) O1 0.0425(13) 0.136(2) 0.0496(14) -0.0464(16) -0.0186(11) 0.0444(15) O2 0.0538(14) 0.0415(12) 0.0417(12) -0.0041(10) -0.0177(11) 0.0134(11) O4 0.138(5) 0.078(3) 0.098(4) 0.000 0.009(3) 0.000 O31 0.0296(9) 0.0190(8) 0.0332(10) -0.0039(7) -0.0051(8) 0.0004(7) O32 0.0291(9) 0.0205(8) 0.0348(10) -0.0010(8) -0.0078(8) 0.0030(7) O51 0.0343(10) 0.0178(9) 0.0529(12) -0.0032(8) -0.0061(9) 0.0008(8) O52 0.0392(11) 0.0304(10) 0.0380(11) -0.0004(8) -0.0174(9) -0.0081(8) N1 0.0208(10) 0.0342(12) 0.0309(12) -0.0067(10) -0.0069(9) 0.0075(9) N2 0.0455(15) 0.0438(15) 0.0452(16) 0.0017(13) -0.0131(13) 0.0089(13) N4 0.172(8) 0.071(4) 0.079(5) 0.000 -0.038(5) 0.000 N11 0.0293(12) 0.0306(12) 0.0275(11) -0.0021(9) -0.0055(9) 0.0032(9) C1 0.0191(11) 0.0299(13) 0.0276(13) -0.0012(11) -0.0045(10) 0.0022(10) C2 0.0237(13) 0.0231(12) 0.0284(13) -0.0068(10) -0.0024(10) -0.0033(10) C3 0.0234(12) 0.0189(11) 0.0249(13) -0.0003(10) 0.0011(10) -0.0003(10) C4 0.0213(12) 0.0221(12) 0.0235(12) 0.0003(10) -0.0025(10) -0.0010(10) C5 0.0234(12) 0.0190(11) 0.0260(13) -0.0012(10) -0.0008(10) -0.0012(10) C6 0.0260(13) 0.0202(12) 0.0281(13) -0.0014(10) -0.0018(10) 0.0040(10) C11 0.0291(14) 0.0589(19) 0.0325(15) -0.0127(14) -0.0068(12) 0.0121(14) C12 0.0376(16) 0.0440(17) 0.0364(16) -0.0118(14) -0.0097(13) 0.0141(14) C13 0.0376(16) 0.0478(18) 0.0358(16) -0.0165(14) -0.0116(13) 0.0114(14) C14 0.0271(13) 0.0451(16) 0.0274(14) -0.0060(12) -0.0046(11) 0.0065(12) C15 0.0424(17) 0.0463(18) 0.0518(19) -0.0165(16) -0.0176(15) 0.0157(14) C16 0.0432(17) 0.0369(16) 0.0431(17) -0.0149(13) -0.0190(14) 0.0115(14) C21 0.0340(19) 0.048(2) 0.032(2) 0.0005(18) -0.0018(16) 0.0037(17) C21B 0.064(12) 0.066(12) 0.038(9) -0.011(8) -0.002(8) -0.011(10) C22 0.039(3) 0.083(4) 0.067(3) 0.014(3) 0.000(2) 0.009(3) C22B 0.12(2) 0.074(17) 0.051(12) 0.013(11) -0.004(13) -0.050(15) C23 0.075(3) 0.036(3) 0.060(3) 0.010(2) -0.025(3) -0.007(2) C23B 0.084(17) 0.12(2) 0.11(2) 0.002(19) -0.015(15) 0.051(18) C31 0.0244(12) 0.0202(12) 0.0253(13) 0.0008(10) 0.0028(10) 0.0003(10) C41 0.050(4) 0.044(4) 0.113(7) 0.020(4) -0.003(4) -0.009(3) C42 0.091(8) 0.102(8) 0.063(6) -0.012(6) 0.012(5) 0.000(6) C43 0.22(2) 0.128(12) 0.30(3) 0.123(17) -0.15(2) -0.055(12) C51 0.0264(12) 0.0216(12) 0.0242(13) -0.0010(10) 0.0011(10) -0.0030(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 Mn1 O52 2.1014(18) 4 ? Mn1 O51 2.1041(18) 8_666 ? Mn1 O2 2.236(2) . ? Mn1 O32 2.2609(18) 8_656 ? Mn1 N11 2.267(2) . ? Mn1 O31 2.3032(17) 8_656 ? Mn1 C31 2.603(2) 8_656 ? O1 C11 1.221(3) . ? O2 C21B 1.19(2) . ? O2 C21 1.275(4) . ? O4 C41 1.234(7) . ? O31 C31 1.265(3) . ? O31 Mn1 2.3032(17) 8_566 ? O32 C31 1.254(3) . ? O32 Mn1 2.2609(18) 8_566 ? O51 C51 1.259(3) . ? O51 Mn1 2.1042(18) 8_556 ? O52 C51 1.248(3) . ? O52 Mn1 2.1014(18) 4_554 ? N1 C11 1.362(3) . ? N1 C1 1.426(3) . ? N1 H1 0.8800 . ? N2 C22B 1.22(2) . ? N2 C21 1.316(4) . ? N2 C22 1.411(5) . ? N2 C23 1.495(5) . ? N2 C21B 1.549(19) . ? N2 C23B 1.57(2) . ? N4 C42 1.261(11) . ? N4 C43 1.405(13) . ? N4 C41 1.472(9) . ? N11 C16 1.325(3) . ? N11 C12 1.333(3) . ? C1 C6 1.389(3) . ? C1 C2 1.390(3) . ? C2 C3 1.384(3) . ? C2 H2 0.9500 . ? C3 C4 1.388(3) . ? C3 C31 1.500(3) . ? C4 C5 1.382(3) . ? C4 H3 0.9500 . ? C5 C6 1.392(3) . ? C5 C51 1.504(3) . ? C6 H4 0.9500 . ? C11 C14 1.500(4) . ? C12 C13 1.383(4) . ? C12 H5 0.9500 . ? C13 C14 1.373(4) . ? C13 H6 0.9500 . ? C14 C15 1.382(4) . ? C15 C16 1.377(4) . ? C15 H7 0.9500 . ? C16 H8 0.9500 . ? C21 H9 0.9500 . ? C21B H9B 0.9500 . ? C22 H10 0.9800 . ? C22 H11 0.9800 . ? C22 H12 0.9800 . ? C22B H10B 0.9800 . ? C22B H11B 0.9800 . ? C22B H12B 0.9800 . ? C23 H13 0.9800 . ? C23 H14 0.9800 . ? C23 H15 0.9800 . ? C23B H13B 0.9800 . ? C23B H14B 0.9800 . ? C23B H15B 0.9800 . ? C31 Mn1 2.603(2) 8_566 ? C41 H16 0.9500 . ? C42 H17 0.9800 . ? C42 H18 0.9800 . ? C42 H19 0.9800 . ? C43 H20 0.9800 . ? C43 H21 0.9800 . ? C43 H22 0.9800 . ? 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 O52 Mn1 O51 112.47(7) 4 8_666 ? O52 Mn1 O2 87.78(9) 4 . ? O51 Mn1 O2 92.25(8) 8_666 . ? O52 Mn1 O32 94.02(7) 4 8_656 ? O51 Mn1 O32 153.22(7) 8_666 8_656 ? O2 Mn1 O32 84.66(7) . 8_656 ? O52 Mn1 N11 91.00(8) 4 . ? O51 Mn1 N11 95.35(8) 8_666 . ? O2 Mn1 N11 172.18(8) . . ? O32 Mn1 N11 87.72(7) 8_656 . ? O52 Mn1 O31 151.16(7) 4 8_656 ? O51 Mn1 O31 95.65(7) 8_666 8_656 ? O2 Mn1 O31 84.74(7) . 8_656 ? O32 Mn1 O31 57.60(6) 8_656 8_656 ? N11 Mn1 O31 92.68(7) . 8_656 ? O52 Mn1 C31 122.16(7) 4 8_656 ? O51 Mn1 C31 124.45(8) 8_666 8_656 ? O2 Mn1 C31 81.04(8) . 8_656 ? O32 Mn1 C31 28.79(7) 8_656 8_656 ? N11 Mn1 C31 93.11(8) . 8_656 ? O31 Mn1 C31 29.08(7) 8_656 8_656 ? C21B O2 C21 68.1(9) . . ? C21B O2 Mn1 123.9(8) . . ? C21 O2 Mn1 114.4(2) . . ? C31 O31 Mn1 88.71(14) . 8_566 ? C31 O32 Mn1 90.91(14) . 8_566 ? C51 O51 Mn1 122.64(16) . 8_556 ? C51 O52 Mn1 167.07(19) . 4_554 ? C11 N1 C1 120.8(2) . . ? C11 N1 H1 119.6 . . ? C1 N1 H1 119.6 . . ? C22B N2 C21 72.2(14) . . ? C22B N2 C22 164.7(14) . . ? C21 N2 C22 122.5(4) . . ? C22B N2 C23 46.5(13) . . ? C21 N2 C23 118.4(4) . . ? C22 N2 C23 119.1(4) . . ? C22B N2 C21B 129.2(15) . . ? C21 N2 C21B 57.0(8) . . ? C22 N2 C21B 65.5(8) . . ? C23 N2 C21B 174.8(8) . . ? C22B N2 C23B 121.3(17) . . ? C21 N2 C23B 163.3(11) . . ? C22 N2 C23B 45.3(12) . . ? C23 N2 C23B 74.9(12) . . ? C21B N2 C23B 109.1(14) . . ? C42 N4 C43 121.7(13) . . ? C42 N4 C41 124.3(8) . . ? C43 N4 C41 113.8(9) . . ? C16 N11 C12 117.2(2) . . ? C16 N11 Mn1 119.50(17) . . ? C12 N11 Mn1 122.82(18) . . ? C6 C1 C2 119.9(2) . . ? C6 C1 N1 120.5(2) . . ? C2 C1 N1 119.6(2) . . ? C3 C2 C1 120.3(2) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.7(2) . . ? C2 C3 C31 119.4(2) . . ? C4 C3 C31 120.9(2) . . ? C5 C4 C3 120.4(2) . . ? C5 C4 H3 119.8 . . ? C3 C4 H3 119.8 . . ? C4 C5 C6 120.0(2) . . ? C4 C5 C51 120.0(2) . . ? C6 C5 C51 119.9(2) . . ? C1 C6 C5 119.8(2) . . ? C1 C6 H4 120.1 . . ? C5 C6 H4 120.1 . . ? O1 C11 N1 123.1(2) . . ? O1 C11 C14 119.5(3) . . ? N1 C11 C14 117.4(2) . . ? N11 C12 C13 123.4(3) . . ? N11 C12 H5 118.3 . . ? C13 C12 H5 118.3 . . ? C14 C13 C12 118.8(3) . . ? C14 C13 H6 120.6 . . ? C12 C13 H6 120.6 . . ? C13 C14 C15 118.0(2) . . ? C13 C14 C11 125.3(3) . . ? C15 C14 C11 116.6(2) . . ? C16 C15 C14 119.2(3) . . ? C16 C15 H7 120.4 . . ? C14 C15 H7 120.4 . . ? N11 C16 C15 123.3(3) . . ? N11 C16 H8 118.4 . . ? C15 C16 H8 118.4 . . ? O2 C21 N2 123.0(3) . . ? O2 C21 H9 118.5 . . ? N2 C21 H9 118.5 . . ? O2 C21B N2 111.7(13) . . ? O2 C21B H9B 124.1 . . ? N2 C21B H9B 124.1 . . ? N2 C22 H10 109.5 . . ? N2 C22 H11 109.5 . . ? H10 C22 H11 109.5 . . ? N2 C22 H12 109.5 . . ? H10 C22 H12 109.5 . . ? H11 C22 H12 109.5 . . ? N2 C22B H10B 109.5 . . ? N2 C22B H11B 109.5 . . ? H10B C22B H11B 109.5 . . ? N2 C22B H12B 109.5 . . ? H10B C22B H12B 109.5 . . ? H11B C22B H12B 109.5 . . ? N2 C23 H13 109.5 . . ? N2 C23 H14 109.5 . . ? H13 C23 H14 109.5 . . ? N2 C23 H15 109.5 . . ? H13 C23 H15 109.5 . . ? H14 C23 H15 109.5 . . ? N2 C23B H13B 109.5 . . ? N2 C23B H14B 109.5 . . ? H13B C23B H14B 109.5 . . ? N2 C23B H15B 109.5 . . ? H13B C23B H15B 109.5 . . ? H14B C23B H15B 109.5 . . ? O32 C31 O31 121.6(2) . . ? O32 C31 C3 118.5(2) . . ? O31 C31 C3 119.9(2) . . ? O32 C31 Mn1 60.29(12) . 8_566 ? O31 C31 Mn1 62.22(12) . 8_566 ? C3 C31 Mn1 168.31(17) . 8_566 ? O4 C41 N4 108.7(6) . . ? O4 C41 H16 125.6 . . ? N4 C41 H16 125.6 . . ? N4 C42 H17 109.5 . . ? N4 C42 H18 109.5 . . ? H17 C42 H18 109.5 . . ? N4 C42 H19 109.5 . . ? H17 C42 H19 109.5 . . ? H18 C42 H19 109.5 . . ? N4 C43 H20 109.5 . . ? N4 C43 H21 109.5 . . ? H20 C43 H21 109.5 . . ? N4 C43 H22 109.5 . . ? H20 C43 H22 109.5 . . ? H21 C43 H22 109.5 . . ? O52 C51 O51 123.7(2) . . ? O52 C51 C5 118.1(2) . . ? O51 C51 C5 118.2(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 O52 Mn1 O2 C21B 154.2(11) 4 . . . ? O51 Mn1 O2 C21B -93.4(11) 8_666 . . . ? O32 Mn1 O2 C21B 59.9(11) 8_656 . . . ? O31 Mn1 O2 C21B 2.1(11) 8_656 . . . ? C31 Mn1 O2 C21B 31.1(11) 8_656 . . . ? O52 Mn1 O2 C21 75.1(2) 4 . . . ? O51 Mn1 O2 C21 -172.5(2) 8_666 . . . ? O32 Mn1 O2 C21 -19.2(2) 8_656 . . . ? O31 Mn1 O2 C21 -77.1(2) 8_656 . . . ? C31 Mn1 O2 C21 -48.0(2) 8_656 . . . ? O52 Mn1 N11 C16 47.2(2) 4 . . . ? O51 Mn1 N11 C16 -65.5(2) 8_666 . . . ? O32 Mn1 N11 C16 141.1(2) 8_656 . . . ? O31 Mn1 N11 C16 -161.5(2) 8_656 . . . ? C31 Mn1 N11 C16 169.4(2) 8_656 . . . ? O52 Mn1 N11 C12 -124.2(2) 4 . . . ? O51 Mn1 N11 C12 123.1(2) 8_666 . . . ? O32 Mn1 N11 C12 -30.2(2) 8_656 . . . ? O31 Mn1 N11 C12 27.2(2) 8_656 . . . ? C31 Mn1 N11 C12 -1.9(2) 8_656 . . . ? C11 N1 C1 C6 -134.8(3) . . . . ? C11 N1 C1 C2 45.7(4) . . . . ? C6 C1 C2 C3 -0.4(4) . . . . ? N1 C1 C2 C3 179.2(2) . . . . ? C1 C2 C3 C4 -0.5(4) . . . . ? C1 C2 C3 C31 -178.5(2) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? C31 C3 C4 C5 179.2(2) . . . . ? C3 C4 C5 C6 -1.1(4) . . . . ? C3 C4 C5 C51 177.2(2) . . . . ? C2 C1 C6 C5 0.5(4) . . . . ? N1 C1 C6 C5 -179.0(2) . . . . ? C4 C5 C6 C1 0.3(4) . . . . ? C51 C5 C6 C1 -178.0(2) . . . . ? C1 N1 C11 O1 3.4(5) . . . . ? C1 N1 C11 C14 -176.2(2) . . . . ? C16 N11 C12 C13 -2.0(4) . . . . ? Mn1 N11 C12 C13 169.6(2) . . . . ? N11 C12 C13 C14 0.5(5) . . . . ? C12 C13 C14 C15 1.1(5) . . . . ? C12 C13 C14 C11 -175.4(3) . . . . ? O1 C11 C14 C13 157.2(3) . . . . ? N1 C11 C14 C13 -23.2(5) . . . . ? O1 C11 C14 C15 -19.3(5) . . . . ? N1 C11 C14 C15 160.3(3) . . . . ? C13 C14 C15 C16 -1.2(5) . . . . ? C11 C14 C15 C16 175.6(3) . . . . ? C12 N11 C16 C15 1.9(5) . . . . ? Mn1 N11 C16 C15 -169.9(3) . . . . ? C14 C15 C16 N11 -0.4(5) . . . . ? C21B O2 C21 N2 3.6(9) . . . . ? Mn1 O2 C21 N2 122.0(3) . . . . ? C22B N2 C21 O2 174.7(11) . . . . ? C22 N2 C21 O2 -0.6(6) . . . . ? C23 N2 C21 O2 179.9(3) . . . . ? C21B N2 C21 O2 -3.0(7) . . . . ? C23B N2 C21 O2 -40(4) . . . . ? C21 O2 C21B N2 -2.7(7) . . . . ? Mn1 O2 C21B N2 -108.2(10) . . . . ? C22B N2 C21B O2 0(2) . . . . ? C21 N2 C21B O2 2.9(7) . . . . ? C22 N2 C21B O2 -174.8(13) . . . . ? C23B N2 C21B O2 172.4(13) . . . . ? Mn1 O32 C31 O31 11.0(2) 8_566 . . . ? Mn1 O32 C31 C3 -166.69(19) 8_566 . . . ? Mn1 O31 C31 O32 -10.8(2) 8_566 . . . ? Mn1 O31 C31 C3 166.9(2) 8_566 . . . ? C2 C3 C31 O32 179.2(2) . . . . ? C4 C3 C31 O32 1.1(4) . . . . ? C2 C3 C31 O31 1.5(4) . . . . ? C4 C3 C31 O31 -176.6(2) . . . . ? C2 C3 C31 Mn1 98.5(9) . . . 8_566 ? C4 C3 C31 Mn1 -79.5(9) . . . 8_566 ? O4 O4 C41 N4 0(100) 7_656 . . . ? N4 N4 C41 O4 0.00(15) 7_656 . . . ? C42 N4 C41 O4 0.1(10) . . . . ? C43 N4 C41 O4 -175.3(9) . . . . ? Mn1 O52 C51 O51 -82.9(8) 4_554 . . . ? Mn1 O52 C51 C5 99.3(7) 4_554 . . . ? Mn1 O51 C51 O52 -8.3(4) 8_556 . . . ? Mn1 O51 C51 C5 169.49(16) 8_556 . . . ? C4 C5 C51 O52 1.5(4) . . . . ? C6 C5 C51 O52 179.8(2) . . . . ? C4 C5 C51 O51 -176.4(2) . . . . ? C6 C5 C51 O51 1.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.326 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.065 data_2 _database_code_depnum_ccdc_archive 'CCDC 751968' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 Mn N2 O11' _chemical_formula_weight 447.26 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5082(8) _cell_length_b 10.0409(10) _cell_length_c 13.2633(13) _cell_angle_alpha 71.085(2) _cell_angle_beta 77.8090(10) _cell_angle_gamma 73.521(2) _cell_volume 899.19(16) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3396 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 28.18 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.652 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 462 _exptl_absorpt_coefficient_mu 0.799 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.858 _exptl_absorpt_correction_T_max 0.909 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 4489 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3106 _reflns_number_gt 2888 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0610P)^2^+0.4424P] 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 3106 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1045 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 Mn1 Mn 0.72346(5) 0.70949(3) 0.08864(2) 0.02189(14) Uani 1 1 d . . . C14 C 0.7253(3) 1.4291(2) 0.17761(19) 0.0244(5) Uani 1 1 d . . . C4 C 0.7339(3) 1.0742(2) 0.39417(17) 0.0218(5) Uani 1 1 d . . . C5 C 0.7300(3) 1.2188(2) 0.34296(18) 0.0229(5) Uani 1 1 d . . . H5 H 0.7282 1.2803 0.3828 0.028 Uiso 1 1 calc R . . C2 C 0.7280(3) 1.0366(2) 0.22482(17) 0.0214(5) Uani 1 1 d . . . C1 C 0.7213(3) 0.9368(2) 0.16307(18) 0.0233(5) Uani 1 1 d . . . C8 C 0.8076(3) 0.8872(3) 0.56293(18) 0.0269(5) Uani 1 1 d . . . C7 C 0.7283(3) 1.1806(2) 0.17314(17) 0.0221(5) Uani 1 1 d . . . H7 H 0.7283 1.2159 0.0991 0.027 Uiso 1 1 calc R . . C3 C 0.7320(3) 0.9829(2) 0.33490(17) 0.0231(5) Uani 1 1 d . . . H3 H 0.7336 0.8859 0.3692 0.028 Uiso 1 1 calc R . . C6 C 0.7286(3) 1.2727(2) 0.23249(18) 0.0217(5) Uani 1 1 d . . . C9 C 0.7828(3) 0.8574(2) 0.68272(18) 0.0249(5) Uani 1 1 d . . . C10 C 0.7414(4) 0.7266(3) 0.74457(19) 0.0295(5) Uani 1 1 d . . . H10 H 0.7280 0.6613 0.7120 0.035 Uiso 1 1 calc R . . C13 C 0.8059(3) 0.9487(3) 0.73436(19) 0.0274(5) Uani 1 1 d . . . H13 H 0.8311 1.0382 0.6952 0.033 Uiso 1 1 calc R . . C12 C 0.7913(3) 0.9056(3) 0.84526(19) 0.0290(5) Uani 1 1 d . . . H12 H 0.8127 0.9662 0.8793 0.035 Uiso 1 1 calc R . . C11 C 0.7206(4) 0.6948(3) 0.85447(19) 0.0302(5) Uani 1 1 d . . . H11 H 0.6858 0.6092 0.8952 0.036 Uiso 1 1 calc R . . N2 N 0.7478(3) 0.7806(2) 0.90619(15) 0.0258(4) Uani 1 1 d . . . N1 N 0.7358(3) 1.0240(2) 0.50689(14) 0.0257(4) Uani 1 1 d . . . H1 H 0.6870 1.0863 0.5427 0.031 Uiso 1 1 calc R . . O3 O 0.7499(3) 1.47345(17) 0.07719(13) 0.0320(4) Uani 1 1 d . . . O4 O 0.6968(3) 1.51432(17) 0.23392(14) 0.0342(4) Uani 1 1 d . . . O2 O 0.7103(3) 0.98194(19) 0.06509(13) 0.0355(4) Uani 1 1 d . . . O1 O 0.7287(3) 0.80513(17) 0.21417(13) 0.0328(4) Uani 1 1 d . . . O1W O 0.4250(2) 0.7694(2) 0.08344(15) 0.0379(4) Uani 1 1 d . . . H1WB H 0.3872 0.8576 0.0493 0.045 Uiso 1 1 d R . . H1WA H 0.3629 0.7512 0.1458 0.045 Uiso 1 1 d R . . O2W O 1.0263(3) 0.6626(2) 0.06830(15) 0.0411(5) Uani 1 1 d . . . H2WB H 1.0770 0.5978 0.0360 0.049 Uiso 1 1 d R . . H2WA H 1.0699 0.6404 0.1273 0.049 Uiso 1 1 d R . . O5 O 0.8883(3) 0.7898(2) 0.52109(14) 0.0492(6) Uani 1 1 d . . . O4W O 0.4609(3) 0.7383(2) 0.40485(17) 0.0500(5) Uani 1 1 d . . . H4WA H 0.4235 0.6652 0.4065 0.060 Uiso 1 1 d R . . H4WB H 0.5391 0.7567 0.3486 0.060 Uiso 1 1 d R . . O3W O 0.9017(4) 0.4977(3) 0.3986(2) 0.0671(7) Uani 1 1 d . . . H3WA H 0.8273 0.5007 0.4563 0.080 Uiso 1 1 d R . . H3WB H 0.8388 0.5026 0.3507 0.080 Uiso 1 1 d R . . O5W O 0.1415(3) 0.6935(3) 0.24796(18) 0.0683(7) Uani 1 1 d . . . H5WA H 0.2251 0.7186 0.1964 0.082 Uiso 1 1 d R . . H5WB H 0.1957 0.6320 0.3000 0.082 Uiso 1 1 d R . . O6W O 0.3343(4) 0.4912(3) 0.4135(2) 0.0805(8) Uani 1 1 d . . . H6WA H 0.2630 0.4934 0.4723 0.097 Uiso 1 1 d R . . H6WB H 0.2776 0.5523 0.3623 0.097 Uiso 1 1 d 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 Mn1 0.0320(2) 0.0179(2) 0.0157(2) -0.00381(14) -0.00414(14) -0.00602(15) C14 0.0294(12) 0.0188(11) 0.0240(12) -0.0041(9) -0.0049(9) -0.0053(9) C4 0.0294(12) 0.0208(11) 0.0149(10) -0.0029(9) -0.0038(9) -0.0072(9) C5 0.0303(12) 0.0220(12) 0.0193(11) -0.0092(9) -0.0023(9) -0.0074(9) C2 0.0264(12) 0.0191(11) 0.0191(11) -0.0059(9) -0.0028(9) -0.0055(9) C1 0.0283(12) 0.0211(12) 0.0220(12) -0.0080(9) -0.0037(9) -0.0056(9) C8 0.0372(13) 0.0249(12) 0.0186(11) -0.0041(10) -0.0065(10) -0.0072(10) C7 0.0305(12) 0.0208(11) 0.0145(10) -0.0035(9) -0.0038(9) -0.0063(9) C3 0.0339(13) 0.0183(11) 0.0171(11) -0.0025(9) -0.0044(9) -0.0082(9) C6 0.0272(12) 0.0172(11) 0.0191(11) -0.0029(9) -0.0034(9) -0.0052(9) C9 0.0293(12) 0.0235(12) 0.0187(11) -0.0033(9) -0.0044(9) -0.0032(9) C10 0.0425(14) 0.0265(13) 0.0222(12) -0.0069(10) -0.0076(10) -0.0097(11) C13 0.0380(13) 0.0217(12) 0.0206(11) -0.0016(9) -0.0050(10) -0.0085(10) C12 0.0389(14) 0.0274(13) 0.0219(12) -0.0084(10) -0.0045(10) -0.0074(11) C11 0.0421(14) 0.0236(12) 0.0218(12) -0.0005(10) -0.0054(10) -0.0089(11) N2 0.0348(11) 0.0232(10) 0.0175(9) -0.0037(8) -0.0044(8) -0.0055(8) N1 0.0430(12) 0.0206(10) 0.0141(9) -0.0051(8) -0.0042(8) -0.0078(9) O3 0.0527(11) 0.0214(9) 0.0177(8) -0.0004(7) -0.0034(7) -0.0091(8) O4 0.0607(12) 0.0173(8) 0.0261(9) -0.0063(7) -0.0080(8) -0.0097(8) O2 0.0587(12) 0.0294(9) 0.0204(9) -0.0082(7) -0.0113(8) -0.0077(8) O1 0.0571(11) 0.0184(8) 0.0263(9) -0.0076(7) -0.0065(8) -0.0118(8) O1W 0.0342(10) 0.0358(10) 0.0322(10) 0.0024(8) -0.0046(8) -0.0043(8) O2W 0.0347(10) 0.0549(12) 0.0374(11) -0.0236(9) -0.0050(8) -0.0037(9) O5 0.0840(15) 0.0307(10) 0.0237(10) -0.0110(8) -0.0143(10) 0.0099(10) O4W 0.0633(14) 0.0427(12) 0.0459(12) -0.0201(10) 0.0109(10) -0.0200(10) O3W 0.0836(18) 0.0645(16) 0.0591(15) -0.0183(12) -0.0310(13) -0.0098(13) O5W 0.0618(15) 0.099(2) 0.0383(12) -0.0017(13) 0.0001(11) -0.0347(14) O6W 0.0757(18) 0.083(2) 0.086(2) -0.0182(16) -0.0220(15) -0.0218(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1W 2.1592(18) . ? Mn1 O2W 2.1631(19) . ? Mn1 O1 2.1867(17) . ? Mn1 N2 2.2729(19) 1_554 ? Mn1 O4 2.2814(17) 1_545 ? Mn1 O3 2.3734(17) 1_545 ? C14 O3 1.251(3) . ? C14 O4 1.257(3) . ? C14 C6 1.497(3) . ? C4 C5 1.384(3) . ? C4 C3 1.392(3) . ? C4 N1 1.416(3) . ? C5 C6 1.389(3) . ? C5 H5 0.9300 . ? C2 C7 1.386(3) . ? C2 C3 1.387(3) . ? C2 C1 1.502(3) . ? C1 O2 1.242(3) . ? C1 O1 1.266(3) . ? C8 O5 1.227(3) . ? C8 N1 1.348(3) . ? C8 C9 1.499(3) . ? C7 C6 1.395(3) . ? C7 H7 0.9300 . ? C3 H3 0.9300 . ? C9 C13 1.373(3) . ? C9 C10 1.386(3) . ? C10 C11 1.372(3) . ? C10 H10 0.9300 . ? C13 C12 1.382(3) . ? C13 H13 0.9300 . ? C12 N2 1.341(3) . ? C12 H12 0.9300 . ? C11 N2 1.340(3) . ? C11 H11 0.9300 . ? N2 Mn1 2.2729(19) 1_556 ? N1 H1 0.8600 . ? O3 Mn1 2.3734(17) 1_565 ? O4 Mn1 2.2814(17) 1_565 ? O1W H1WB 0.8500 . ? O1W H1WA 0.8500 . ? O2W H2WB 0.8501 . ? O2W H2WA 0.8500 . ? O4W H4WA 0.8499 . ? O4W H4WB 0.8499 . ? O3W H3WA 0.8500 . ? O3W H3WB 0.8501 . ? O5W H5WA 0.8500 . ? O5W H5WB 0.8500 . ? O6W H6WA 0.8500 . ? O6W H6WB 0.8500 . ? 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 O1W Mn1 O2W 171.53(7) . . ? O1W Mn1 O1 98.70(7) . . ? O2W Mn1 O1 86.84(7) . . ? O1W Mn1 N2 85.10(7) . 1_554 ? O2W Mn1 N2 86.48(7) . 1_554 ? O1 Mn1 N2 136.45(7) . 1_554 ? O1W Mn1 O4 91.63(7) . 1_545 ? O2W Mn1 O4 95.53(7) . 1_545 ? O1 Mn1 O4 81.59(6) . 1_545 ? N2 Mn1 O4 141.91(7) 1_554 1_545 ? O1W Mn1 O3 92.53(7) . 1_545 ? O2W Mn1 O3 87.78(7) . 1_545 ? O1 Mn1 O3 136.29(6) . 1_545 ? N2 Mn1 O3 86.33(6) 1_554 1_545 ? O4 Mn1 O3 55.85(6) 1_545 1_545 ? O3 C14 O4 120.9(2) . . ? O3 C14 C6 120.1(2) . . ? O4 C14 C6 119.0(2) . . ? C5 C4 C3 119.7(2) . . ? C5 C4 N1 118.44(19) . . ? C3 C4 N1 121.80(19) . . ? C4 C5 C6 120.5(2) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C2 C3 120.2(2) . . ? C7 C2 C1 120.7(2) . . ? C3 C2 C1 119.04(19) . . ? O2 C1 O1 121.3(2) . . ? O2 C1 C2 121.0(2) . . ? O1 C1 C2 117.69(19) . . ? O5 C8 N1 123.6(2) . . ? O5 C8 C9 120.2(2) . . ? N1 C8 C9 116.2(2) . . ? C2 C7 C6 119.9(2) . . ? C2 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C2 C3 C4 120.0(2) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C6 C7 119.66(19) . . ? C5 C6 C14 120.1(2) . . ? C7 C6 C14 120.2(2) . . ? C13 C9 C10 118.4(2) . . ? C13 C9 C8 124.1(2) . . ? C10 C9 C8 117.4(2) . . ? C11 C10 C9 119.0(2) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C9 C13 C12 119.0(2) . . ? C9 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? N2 C12 C13 123.2(2) . . ? N2 C12 H12 118.4 . . ? C13 C12 H12 118.4 . . ? N2 C11 C10 123.4(2) . . ? N2 C11 H11 118.3 . . ? C10 C11 H11 118.3 . . ? C11 N2 C12 116.9(2) . . ? C11 N2 Mn1 119.85(15) . 1_556 ? C12 N2 Mn1 123.28(16) . 1_556 ? C8 N1 C4 125.68(19) . . ? C8 N1 H1 117.2 . . ? C4 N1 H1 117.2 . . ? C14 O3 Mn1 89.56(13) . 1_565 ? C14 O4 Mn1 93.67(14) . 1_565 ? C1 O1 Mn1 102.84(14) . . ? Mn1 O1W H1WB 112.4 . . ? Mn1 O1W H1WA 112.3 . . ? H1WB O1W H1WA 110.0 . . ? Mn1 O2W H2WB 112.8 . . ? Mn1 O2W H2WA 112.7 . . ? H2WB O2W H2WA 110.3 . . ? H4WA O4W H4WB 108.4 . . ? H3WA O3W H3WB 108.4 . . ? H5WA O5W H5WB 108.3 . . ? H6WA O6W H6WB 108.4 . . ? 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 C3 C4 C5 C6 -1.5(3) . . . . ? N1 C4 C5 C6 179.8(2) . . . . ? C7 C2 C1 O2 -2.1(3) . . . . ? C3 C2 C1 O2 177.2(2) . . . . ? C7 C2 C1 O1 177.3(2) . . . . ? C3 C2 C1 O1 -3.3(3) . . . . ? C3 C2 C7 C6 -1.4(3) . . . . ? C1 C2 C7 C6 178.0(2) . . . . ? C7 C2 C3 C4 0.9(3) . . . . ? C1 C2 C3 C4 -178.5(2) . . . . ? C5 C4 C3 C2 0.6(3) . . . . ? N1 C4 C3 C2 179.3(2) . . . . ? C4 C5 C6 C7 1.0(3) . . . . ? C4 C5 C6 C14 -179.7(2) . . . . ? C2 C7 C6 C5 0.5(3) . . . . ? C2 C7 C6 C14 -178.8(2) . . . . ? O3 C14 C6 C5 170.2(2) . . . . ? O4 C14 C6 C5 -10.1(3) . . . . ? O3 C14 C6 C7 -10.5(3) . . . . ? O4 C14 C6 C7 169.2(2) . . . . ? O5 C8 C9 C13 138.3(3) . . . . ? N1 C8 C9 C13 -42.1(3) . . . . ? O5 C8 C9 C10 -38.9(4) . . . . ? N1 C8 C9 C10 140.6(2) . . . . ? C13 C9 C10 C11 1.6(4) . . . . ? C8 C9 C10 C11 179.0(2) . . . . ? C10 C9 C13 C12 1.4(4) . . . . ? C8 C9 C13 C12 -175.8(2) . . . . ? C9 C13 C12 N2 -2.8(4) . . . . ? C9 C10 C11 N2 -3.6(4) . . . . ? C10 C11 N2 C12 2.3(4) . . . . ? C10 C11 N2 Mn1 -176.79(19) . . . 1_556 ? C13 C12 N2 C11 1.0(4) . . . . ? C13 C12 N2 Mn1 -179.97(18) . . . 1_556 ? O5 C8 N1 C4 3.3(4) . . . . ? C9 C8 N1 C4 -176.2(2) . . . . ? C5 C4 N1 C8 -153.6(2) . . . . ? C3 C4 N1 C8 27.7(4) . . . . ? O4 C14 O3 Mn1 1.5(2) . . . 1_565 ? C6 C14 O3 Mn1 -178.77(19) . . . 1_565 ? O3 C14 O4 Mn1 -1.6(2) . . . 1_565 ? C6 C14 O4 Mn1 178.70(18) . . . 1_565 ? O2 C1 O1 Mn1 1.2(3) . . . . ? C2 C1 O1 Mn1 -178.23(16) . . . . ? O1W Mn1 O1 C1 -81.97(16) . . . . ? O2W Mn1 O1 C1 91.59(16) . . . . ? N2 Mn1 O1 C1 10.1(2) 1_554 . . . ? O4 Mn1 O1 C1 -172.34(16) 1_545 . . . ? O3 Mn1 O1 C1 175.05(13) 1_545 . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.548 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.110 data_3 _database_code_depnum_ccdc_archive 'CCDC 751969' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Co N2 O8' _chemical_formula_weight 397.20 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 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0877(11) _cell_length_b 9.9836(14) _cell_length_c 10.5561(14) _cell_angle_alpha 64.586(2) _cell_angle_beta 84.2240(10) _cell_angle_gamma 82.821(2) _cell_volume 762.78(18) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4024 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.29 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.729 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 406 _exptl_absorpt_coefficient_mu 1.174 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.844 _exptl_absorpt_correction_T_max 0.899 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 3907 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0552 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2714 _reflns_number_gt 2381 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 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^+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 2714 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1075 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.63814(5) 0.76407(4) 0.63330(4) 0.02097(17) Uani 1 1 d . . . C1 C 0.5276(4) 0.5119(3) 0.7326(3) 0.0223(7) Uani 1 1 d . . . C2 C 0.4726(4) 0.3608(3) 0.7720(3) 0.0203(7) Uani 1 1 d . . . C3 C 0.3738(4) 0.2904(3) 0.8931(3) 0.0227(7) Uani 1 1 d . . . H3 H 0.3366 0.3389 0.9501 0.027 Uiso 1 1 calc R . . C4 C 0.3306(4) 0.1477(3) 0.9294(3) 0.0199(7) Uani 1 1 d . . . C5 C 0.3912(4) 0.0739(3) 0.8454(3) 0.0208(7) Uani 1 1 d . . . H5 H 0.3688 -0.0239 0.8719 0.025 Uiso 1 1 calc R . . C6 C 0.4847(4) 0.1474(3) 0.7224(3) 0.0185(6) Uani 1 1 d . . . C7 C 0.5241(4) 0.2901(3) 0.6848(3) 0.0212(7) Uani 1 1 d . . . H7 H 0.5851 0.3391 0.6011 0.025 Uiso 1 1 calc R . . C8 C 0.1612(4) -0.0490(3) 1.1020(3) 0.0231(7) Uani 1 1 d . . . C9 C 0.0512(4) -0.0881(4) 1.2345(3) 0.0235(7) Uani 1 1 d . . . C10 C -0.0290(5) 0.0156(4) 1.2784(3) 0.0328(8) Uani 1 1 d . . . H10 H -0.0093 0.1154 1.2302 0.039 Uiso 1 1 calc R . . C11 C -0.1396(5) -0.0302(4) 1.3952(3) 0.0325(8) Uani 1 1 d . . . H11 H -0.1921 0.0411 1.4242 0.039 Uiso 1 1 calc R . . C12 C -0.0947(4) -0.2708(4) 1.4241(4) 0.0321(8) Uani 1 1 d . . . H12 H -0.1161 -0.3700 1.4741 0.039 Uiso 1 1 calc R . . C13 C 0.0164(4) -0.2350(4) 1.3094(3) 0.0316(8) Uani 1 1 d . . . H13 H 0.0675 -0.3083 1.2826 0.038 Uiso 1 1 calc R . . C14 C 0.5504(4) 0.0679(4) 0.6328(3) 0.0227(7) Uani 1 1 d . . . N1 N 0.2295(3) 0.0815(3) 1.0538(3) 0.0232(6) Uani 1 1 d . . . H1 H 0.2093 0.1303 1.1047 0.028 Uiso 1 1 calc R . . N2 N -0.1742(3) -0.1707(3) 1.4678(3) 0.0248(6) Uani 1 1 d . . . O1 O 0.4607(3) 0.5948(2) 0.7902(2) 0.0318(6) Uani 1 1 d . . . O2 O 0.6406(3) 0.5561(2) 0.6372(2) 0.0286(5) Uani 1 1 d . . . O3 O 0.5612(3) 0.1425(2) 0.5012(2) 0.0251(5) Uani 1 1 d . . . O4 O 0.5933(3) -0.0699(2) 0.6958(2) 0.0276(5) Uani 1 1 d . . . O5 O 0.1799(3) -0.1324(3) 1.0439(2) 0.0364(6) Uani 1 1 d . . . O1W O 0.8210(3) 0.6725(3) 0.7892(2) 0.0333(6) Uani 1 1 d . . . H1WB H 0.8093 0.7216 0.8388 0.040 Uiso 1 1 d R . . H1WA H 0.9173 0.6842 0.7478 0.040 Uiso 1 1 d R . . O2W O 0.7781(4) 0.3959(3) 0.9980(3) 0.0549(8) Uani 1 1 d . . . H2WA H 0.7060 0.4018 1.0602 0.066 Uiso 1 1 d R . . H2WB H 0.7889 0.4832 0.9345 0.066 Uiso 1 1 d R . . O3W O 0.1416(4) 0.6569(4) 0.6694(3) 0.0757(10) Uani 1 1 d . . . H3WA H 0.0531 0.6577 0.7199 0.091 Uiso 1 1 d R . . H3WB H 0.2253 0.6369 0.7193 0.091 Uiso 1 1 d 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 Co1 0.0271(3) 0.0168(3) 0.0205(3) -0.00971(19) 0.00784(18) -0.00786(17) C1 0.0259(18) 0.0190(16) 0.0222(17) -0.0092(14) 0.0027(13) -0.0040(13) C2 0.0234(17) 0.0149(15) 0.0216(16) -0.0072(13) 0.0047(13) -0.0041(12) C3 0.0273(18) 0.0222(17) 0.0231(16) -0.0143(14) 0.0063(13) -0.0066(13) C4 0.0214(17) 0.0212(16) 0.0163(15) -0.0078(13) 0.0047(12) -0.0046(12) C5 0.0252(17) 0.0155(15) 0.0221(16) -0.0078(13) 0.0014(13) -0.0059(12) C6 0.0205(16) 0.0179(16) 0.0178(15) -0.0088(13) 0.0012(12) -0.0013(12) C7 0.0222(17) 0.0211(17) 0.0187(16) -0.0074(14) 0.0060(13) -0.0056(13) C8 0.0235(18) 0.0228(17) 0.0226(17) -0.0091(14) 0.0025(13) -0.0057(13) C9 0.0215(17) 0.0279(18) 0.0214(16) -0.0105(15) 0.0034(13) -0.0066(14) C10 0.039(2) 0.0250(18) 0.035(2) -0.0138(16) 0.0165(16) -0.0168(15) C11 0.041(2) 0.0282(19) 0.0320(19) -0.0175(16) 0.0138(16) -0.0101(16) C12 0.038(2) 0.0200(18) 0.0333(19) -0.0079(15) 0.0128(16) -0.0074(15) C13 0.037(2) 0.0236(18) 0.0309(19) -0.0110(16) 0.0142(16) -0.0062(15) C14 0.0206(17) 0.0259(18) 0.0278(18) -0.0165(15) 0.0027(13) -0.0077(13) N1 0.0267(15) 0.0247(14) 0.0221(14) -0.0137(12) 0.0098(11) -0.0106(11) N2 0.0255(15) 0.0256(15) 0.0250(14) -0.0118(12) 0.0055(11) -0.0092(12) O1 0.0419(15) 0.0240(13) 0.0342(13) -0.0176(11) 0.0128(11) -0.0113(11) O2 0.0364(14) 0.0208(12) 0.0302(13) -0.0129(10) 0.0149(10) -0.0137(10) O3 0.0301(13) 0.0273(12) 0.0184(11) -0.0112(10) 0.0060(9) -0.0042(10) O4 0.0454(15) 0.0172(12) 0.0241(12) -0.0133(10) -0.0012(10) -0.0002(10) O5 0.0493(17) 0.0292(13) 0.0357(14) -0.0190(12) 0.0203(12) -0.0192(11) O1W 0.0361(15) 0.0321(14) 0.0341(13) -0.0162(11) 0.0007(11) -0.0057(11) O2W 0.078(2) 0.0338(16) 0.0447(16) -0.0122(14) 0.0189(15) -0.0105(14) O3W 0.0368(19) 0.093(3) 0.090(3) -0.034(2) -0.0080(17) 0.0058(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 Co1 O4 2.014(2) 1_565 ? Co1 O2 2.056(2) . ? Co1 O3 2.106(2) 2_666 ? Co1 N2 2.125(3) 1_664 ? Co1 O1W 2.143(2) . ? Co1 O1 2.320(2) . ? Co1 C1 2.519(3) . ? C1 O2 1.256(4) . ? C1 O1 1.266(4) . ? C1 C2 1.496(4) . ? C2 C7 1.388(4) . ? C2 C3 1.390(4) . ? C3 C4 1.388(4) . ? C3 H3 0.9300 . ? C4 C5 1.397(4) . ? C4 N1 1.416(4) . ? C5 C6 1.386(4) . ? C5 H5 0.9300 . ? C6 C7 1.375(4) . ? C6 C14 1.498(4) . ? C7 H7 0.9300 . ? C8 O5 1.216(4) . ? C8 N1 1.348(4) . ? C8 C9 1.507(4) . ? C9 C10 1.374(4) . ? C9 C13 1.385(4) . ? C10 C11 1.388(4) . ? C10 H10 0.9300 . ? C11 N2 1.329(4) . ? C11 H11 0.9300 . ? C12 N2 1.342(4) . ? C12 C13 1.375(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O3 1.263(4) . ? C14 O4 1.264(4) . ? N1 H1 0.8600 . ? N2 Co1 2.125(3) 1_446 ? O3 Co1 2.106(2) 2_666 ? O4 Co1 2.014(2) 1_545 ? O1W H1WB 0.8500 . ? O1W H1WA 0.8500 . ? O2W H2WA 0.8500 . ? O2W H2WB 0.8499 . ? O3W H3WA 0.8500 . ? O3W H3WB 0.8501 . ? 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 159.62(9) 1_565 . ? O4 Co1 O3 89.79(9) 1_565 2_666 ? O2 Co1 O3 94.42(9) . 2_666 ? O4 Co1 N2 106.73(9) 1_565 1_664 ? O2 Co1 N2 92.83(9) . 1_664 ? O3 Co1 N2 94.39(9) 2_666 1_664 ? O4 Co1 O1W 85.57(9) 1_565 . ? O2 Co1 O1W 88.24(9) . . ? O3 Co1 O1W 173.13(8) 2_666 . ? N2 Co1 O1W 91.80(10) 1_664 . ? O4 Co1 O1 100.67(8) 1_565 . ? O2 Co1 O1 59.68(8) . . ? O3 Co1 O1 87.80(9) 2_666 . ? N2 Co1 O1 152.51(9) 1_664 . ? O1W Co1 O1 88.08(9) . . ? O4 Co1 C1 130.49(9) 1_565 . ? O2 Co1 C1 29.73(9) . . ? O3 Co1 C1 90.87(9) 2_666 . ? N2 Co1 C1 122.55(10) 1_664 . ? O1W Co1 C1 88.31(9) . . ? O1 Co1 C1 29.96(8) . . ? O2 C1 O1 120.5(3) . . ? O2 C1 C2 117.7(3) . . ? O1 C1 C2 121.7(3) . . ? O2 C1 Co1 54.27(15) . . ? O1 C1 Co1 66.28(16) . . ? C2 C1 Co1 171.5(2) . . ? C7 C2 C3 119.9(3) . . ? C7 C2 C1 118.4(3) . . ? C3 C2 C1 121.7(3) . . ? C4 C3 C2 120.2(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 119.5(3) . . ? C3 C4 N1 117.8(3) . . ? C5 C4 N1 122.7(3) . . ? C6 C5 C4 119.6(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C7 C6 C5 120.7(3) . . ? C7 C6 C14 119.6(3) . . ? C5 C6 C14 119.6(3) . . ? C6 C7 C2 119.9(3) . . ? C6 C7 H7 120.1 . . ? C2 C7 H7 120.1 . . ? O5 C8 N1 124.4(3) . . ? O5 C8 C9 119.5(3) . . ? N1 C8 C9 116.0(3) . . ? C10 C9 C13 118.0(3) . . ? C10 C9 C8 123.7(3) . . ? C13 C9 C8 118.1(3) . . ? C9 C10 C11 119.3(3) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? N2 C11 C10 123.3(3) . . ? N2 C11 H11 118.4 . . ? C10 C11 H11 118.4 . . ? N2 C12 C13 123.7(3) . . ? N2 C12 H12 118.1 . . ? C13 C12 H12 118.1 . . ? C12 C13 C9 118.9(3) . . ? C12 C13 H13 120.5 . . ? C9 C13 H13 120.5 . . ? O3 C14 O4 124.8(3) . . ? O3 C14 C6 118.3(3) . . ? O4 C14 C6 116.9(3) . . ? C8 N1 C4 127.7(3) . . ? C8 N1 H1 116.2 . . ? C4 N1 H1 116.2 . . ? C11 N2 C12 116.7(3) . . ? C11 N2 Co1 122.9(2) . 1_446 ? C12 N2 Co1 120.1(2) . 1_446 ? C1 O1 Co1 83.76(18) . . ? C1 O2 Co1 96.00(18) . . ? C14 O3 Co1 126.7(2) . 2_666 ? C14 O4 Co1 133.4(2) . 1_545 ? Co1 O1W H1WB 108.5 . . ? Co1 O1W H1WA 108.5 . . ? H1WB O1W H1WA 107.7 . . ? H2WA O2W H2WB 108.5 . . ? H3WA O3W H3WB 108.8 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.500 _refine_diff_density_min -0.642 _refine_diff_density_rms 0.082 data_4 _database_code_depnum_ccdc_archive 'CCDC 751970' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H12 Co N3 O5' _chemical_formula_weight 421.25 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 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6371(10) _cell_length_b 9.6990(12) _cell_length_c 11.8615(14) _cell_angle_alpha 104.913(2) _cell_angle_beta 104.4380(10) _cell_angle_gamma 92.998(2) _cell_volume 815.81(18) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 28.14 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.715 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 1.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.821 _exptl_absorpt_correction_T_max 0.877 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 4173 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2900 _reflns_number_gt 2588 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 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^)+(0.0551P)^2^+0.0264P] 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 2900 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0950 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.42692(5) 0.17548(3) 0.09536(3) 0.02351(14) Uani 1 1 d . . . C1 C 0.3345(3) 0.4230(3) 0.2525(2) 0.0256(6) Uani 1 1 d . . . C2 C 0.4092(3) 0.5780(3) 0.2798(2) 0.0218(5) Uani 1 1 d . . . C3 C 0.5122(3) 0.6477(3) 0.3969(2) 0.0246(6) Uani 1 1 d . . . H3 H 0.5259 0.5997 0.4565 0.030 Uiso 1 1 calc R . . C4 C 0.5952(3) 0.7879(3) 0.4267(2) 0.0238(6) Uani 1 1 d . . . C5 C 0.5657(4) 0.8610(3) 0.3385(2) 0.0267(6) Uani 1 1 d . . . H5 H 0.6146 0.9567 0.3582 0.032 Uiso 1 1 calc R . . C6 C 0.4634(3) 0.7914(3) 0.2210(2) 0.0231(6) Uani 1 1 d . . . C7 C 0.3900(3) 0.6489(3) 0.1902(2) 0.0241(6) Uani 1 1 d . . . H7 H 0.3282 0.6010 0.1103 0.029 Uiso 1 1 calc R . . C8 C 0.8048(4) 0.9789(3) 0.5918(2) 0.0290(6) Uani 1 1 d . . . C9 C 0.9305(3) 1.0134(3) 0.7173(2) 0.0258(6) Uani 1 1 d . . . C10 C 0.9817(4) 0.9161(3) 0.7816(2) 0.0295(6) Uani 1 1 d . . . H10 H 0.9289 0.8207 0.7510 0.035 Uiso 1 1 calc R . . C11 C 1.1117(4) 0.9606(3) 0.8917(2) 0.0293(6) Uani 1 1 d . . . H11 H 1.1455 0.8925 0.9331 0.035 Uiso 1 1 calc R . . C12 C 1.1337(4) 1.1909(3) 0.8822(3) 0.0420(8) Uani 1 1 d . . . H12 H 1.1815 1.2870 0.9174 0.050 Uiso 1 1 calc R . . C13 C 1.0076(4) 1.1542(3) 0.7711(3) 0.0395(8) Uani 1 1 d . . . H13 H 0.9739 1.2245 0.7322 0.047 Uiso 1 1 calc R . . C14 C 0.4421(3) 0.8714(3) 0.1269(2) 0.0247(6) Uani 1 1 d . . . C15 C 0.6920(4) 0.2592(3) 0.3507(2) 0.0323(6) Uani 1 1 d . . . H15 H 0.6208 0.1831 0.3583 0.039 Uiso 1 1 calc R . . C16 C 0.8224(4) 0.3405(3) 0.4522(2) 0.0313(6) Uani 1 1 d . . . H16 H 0.8372 0.3183 0.5255 0.038 Uiso 1 1 calc R . . C17 C 0.9305(3) 0.4539(3) 0.4458(2) 0.0245(6) Uani 1 1 d . . . C18 C 0.9001(4) 0.4787(3) 0.3326(2) 0.0359(7) Uani 1 1 d . . . H18 H 0.9697 0.5540 0.3225 0.043 Uiso 1 1 calc R . . C19 C 0.7680(4) 0.3925(3) 0.2358(2) 0.0345(7) Uani 1 1 d . . . H19 H 0.7515 0.4113 0.1611 0.041 Uiso 1 1 calc R . . N1 N 0.7069(3) 0.8474(2) 0.54563(18) 0.0285(5) Uani 1 1 d . . . H1 H 0.7136 0.7942 0.5941 0.034 Uiso 1 1 calc R . . N2 N 1.1916(3) 1.0952(2) 0.94240(18) 0.0269(5) Uani 1 1 d . . . N3 N 0.6618(3) 0.2833(2) 0.24249(19) 0.0264(5) Uani 1 1 d . . . O1 O 0.3028(3) 0.34654(19) 0.14269(15) 0.0327(5) Uani 1 1 d . . . O2 O 0.3105(3) 0.37767(19) 0.33659(16) 0.0352(5) Uani 1 1 d . . . O3 O 0.4301(3) 0.80012(19) 0.01991(14) 0.0309(4) Uani 1 1 d . . . O4 O 0.4403(3) 1.00472(19) 0.16097(15) 0.0315(4) Uani 1 1 d . . . O5 O 0.7962(3) 1.0701(2) 0.53701(18) 0.0526(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 0.0330(2) 0.0168(2) 0.0156(2) 0.00463(14) -0.00120(14) -0.00484(14) C1 0.0290(14) 0.0189(14) 0.0219(13) 0.0070(11) -0.0059(11) -0.0020(11) C2 0.0282(14) 0.0167(13) 0.0171(12) 0.0040(10) 0.0013(10) -0.0008(10) C3 0.0340(15) 0.0198(14) 0.0167(12) 0.0077(10) -0.0004(11) -0.0024(11) C4 0.0308(14) 0.0195(14) 0.0161(12) 0.0040(10) -0.0003(10) -0.0038(11) C5 0.0366(15) 0.0184(13) 0.0197(13) 0.0064(11) -0.0013(11) -0.0058(11) C6 0.0284(14) 0.0215(14) 0.0166(12) 0.0069(10) 0.0007(10) -0.0025(11) C7 0.0318(14) 0.0200(14) 0.0145(12) 0.0034(10) -0.0017(10) -0.0027(11) C8 0.0369(16) 0.0242(15) 0.0190(13) 0.0060(11) -0.0030(11) -0.0055(12) C9 0.0284(14) 0.0232(14) 0.0208(13) 0.0059(11) -0.0007(11) -0.0036(11) C10 0.0366(15) 0.0171(14) 0.0264(14) 0.0060(11) -0.0045(12) -0.0069(11) C11 0.0351(15) 0.0241(15) 0.0237(14) 0.0084(11) -0.0020(11) -0.0009(12) C12 0.059(2) 0.0200(15) 0.0305(16) 0.0051(12) -0.0128(14) -0.0120(14) C13 0.0537(19) 0.0205(15) 0.0317(15) 0.0116(12) -0.0134(13) -0.0059(13) C14 0.0272(14) 0.0230(14) 0.0191(13) 0.0092(11) -0.0031(10) -0.0085(11) C15 0.0398(16) 0.0252(15) 0.0248(14) 0.0078(12) -0.0016(12) -0.0118(12) C16 0.0415(16) 0.0270(15) 0.0185(13) 0.0086(11) -0.0034(11) -0.0113(12) C17 0.0288(14) 0.0204(14) 0.0197(13) 0.0046(11) 0.0005(11) -0.0015(11) C18 0.0449(17) 0.0333(17) 0.0233(14) 0.0123(12) -0.0022(12) -0.0162(13) C19 0.0438(17) 0.0349(17) 0.0196(13) 0.0108(12) -0.0012(12) -0.0105(13) N1 0.0407(13) 0.0203(12) 0.0164(11) 0.0084(9) -0.0075(9) -0.0090(10) N2 0.0326(12) 0.0213(12) 0.0190(11) 0.0041(9) -0.0035(9) -0.0049(9) N3 0.0323(12) 0.0212(12) 0.0199(11) 0.0053(9) -0.0013(9) -0.0044(9) O1 0.0470(12) 0.0179(10) 0.0202(9) -0.0008(8) -0.0073(8) 0.0021(8) O2 0.0511(12) 0.0233(11) 0.0260(10) 0.0124(8) -0.0011(9) -0.0111(9) O3 0.0430(11) 0.0300(11) 0.0136(9) 0.0066(8) -0.0006(8) -0.0110(9) O4 0.0449(12) 0.0213(10) 0.0236(10) 0.0110(8) -0.0020(8) -0.0064(8) O5 0.0794(17) 0.0295(12) 0.0304(11) 0.0178(10) -0.0220(11) -0.0232(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 O1 1.9791(18) . ? Co1 O4 2.0001(18) 1_545 ? Co1 O3 2.0004(18) 2_665 ? Co1 N2 2.151(2) 1_444 ? Co1 N3 2.159(2) . ? C1 O2 1.236(3) . ? C1 O1 1.278(3) . ? C1 C2 1.503(3) . ? C2 C3 1.387(3) . ? C2 C7 1.390(3) . ? C3 C4 1.388(3) . ? C3 H3 0.9300 . ? C4 C5 1.389(3) . ? C4 N1 1.407(3) . ? C5 C6 1.388(3) . ? C5 H5 0.9300 . ? C6 C7 1.383(3) . ? C6 C14 1.498(3) . ? C7 H7 0.9300 . ? C8 O5 1.221(3) . ? C8 N1 1.350(3) . ? C8 C9 1.499(3) . ? C9 C10 1.374(3) . ? C9 C13 1.378(4) . ? C10 C11 1.377(3) . ? C10 H10 0.9300 . ? C11 N2 1.330(3) . ? C11 H11 0.9300 . ? C12 N2 1.339(3) . ? C12 C13 1.371(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O4 1.253(3) . ? C14 O3 1.257(3) . ? C15 N3 1.329(3) . ? C15 C16 1.376(4) . ? C15 H15 0.9300 . ? C16 C17 1.370(4) . ? C16 H16 0.9300 . ? C17 C18 1.389(3) . ? C17 C17 1.486(5) 2_766 ? C18 C19 1.370(4) . ? C18 H18 0.9300 . ? C19 N3 1.330(3) . ? C19 H19 0.9300 . ? N1 H1 0.8600 . ? N2 Co1 2.151(2) 1_666 ? O3 Co1 2.0004(18) 2_665 ? O4 Co1 2.0001(18) 1_565 ? 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 O4 127.73(8) . 1_545 ? O1 Co1 O3 111.01(8) . 2_665 ? O4 Co1 O3 120.95(8) 1_545 2_665 ? O1 Co1 N2 87.03(8) . 1_444 ? O4 Co1 N2 99.10(8) 1_545 1_444 ? O3 Co1 N2 88.41(8) 2_665 1_444 ? O1 Co1 N3 87.64(8) . . ? O4 Co1 N3 88.66(8) 1_545 . ? O3 Co1 N3 88.19(8) 2_665 . ? N2 Co1 N3 172.21(8) 1_444 . ? O2 C1 O1 124.7(2) . . ? O2 C1 C2 118.7(2) . . ? O1 C1 C2 116.7(2) . . ? C3 C2 C7 119.6(2) . . ? C3 C2 C1 118.0(2) . . ? C7 C2 C1 122.3(2) . . ? C2 C3 C4 121.1(2) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 118.9(2) . . ? C3 C4 N1 117.4(2) . . ? C5 C4 N1 123.7(2) . . ? C6 C5 C4 120.1(2) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C7 C6 C5 120.6(2) . . ? C7 C6 C14 120.7(2) . . ? C5 C6 C14 118.6(2) . . ? C6 C7 C2 119.5(2) . . ? C6 C7 H7 120.3 . . ? C2 C7 H7 120.3 . . ? O5 C8 N1 123.6(2) . . ? O5 C8 C9 118.7(2) . . ? N1 C8 C9 117.6(2) . . ? C10 C9 C13 116.9(2) . . ? C10 C9 C8 125.7(2) . . ? C13 C9 C8 117.3(2) . . ? C9 C10 C11 119.6(2) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? N2 C11 C10 123.9(2) . . ? N2 C11 H11 118.1 . . ? C10 C11 H11 118.1 . . ? N2 C12 C13 123.3(3) . . ? N2 C12 H12 118.3 . . ? C13 C12 H12 118.3 . . ? C12 C13 C9 120.1(3) . . ? C12 C13 H13 120.0 . . ? C9 C13 H13 120.0 . . ? O4 C14 O3 124.9(2) . . ? O4 C14 C6 117.6(2) . . ? O3 C14 C6 117.5(2) . . ? N3 C15 C16 123.8(2) . . ? N3 C15 H15 118.1 . . ? C16 C15 H15 118.1 . . ? C17 C16 C15 120.3(2) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 116.0(2) . . ? C16 C17 C17 121.7(3) . 2_766 ? C18 C17 C17 122.3(3) . 2_766 ? C19 C18 C17 120.1(3) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? N3 C19 C18 123.8(2) . . ? N3 C19 H19 118.1 . . ? C18 C19 H19 118.1 . . ? C8 N1 C4 127.0(2) . . ? C8 N1 H1 116.5 . . ? C4 N1 H1 116.5 . . ? C11 N2 C12 116.1(2) . . ? C11 N2 Co1 128.50(17) . 1_666 ? C12 N2 Co1 114.80(17) . 1_666 ? C19 N3 C15 115.9(2) . . ? C19 N3 Co1 121.69(17) . . ? C15 N3 Co1 121.59(18) . . ? C1 O1 Co1 122.50(15) . . ? C14 O3 Co1 131.30(17) . 2_665 ? C14 O4 Co1 140.36(17) . 1_565 ? 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 C1 C2 C3 24.7(4) . . . . ? O1 C1 C2 C3 -154.2(2) . . . . ? O2 C1 C2 C7 -160.2(3) . . . . ? O1 C1 C2 C7 20.9(4) . . . . ? C7 C2 C3 C4 0.6(4) . . . . ? C1 C2 C3 C4 175.8(2) . . . . ? C2 C3 C4 C5 3.4(4) . . . . ? C2 C3 C4 N1 -175.9(2) . . . . ? C3 C4 C5 C6 -3.7(4) . . . . ? N1 C4 C5 C6 175.6(2) . . . . ? C4 C5 C6 C7 -0.1(4) . . . . ? C4 C5 C6 C14 -177.1(2) . . . . ? C5 C6 C7 C2 4.1(4) . . . . ? C14 C6 C7 C2 -179.0(2) . . . . ? C3 C2 C7 C6 -4.4(4) . . . . ? C1 C2 C7 C6 -179.4(2) . . . . ? O5 C8 C9 C10 -167.1(3) . . . . ? N1 C8 C9 C10 12.9(4) . . . . ? O5 C8 C9 C13 10.2(4) . . . . ? N1 C8 C9 C13 -169.9(3) . . . . ? C13 C9 C10 C11 -3.3(4) . . . . ? C8 C9 C10 C11 173.9(3) . . . . ? C9 C10 C11 N2 1.0(4) . . . . ? N2 C12 C13 C9 1.5(5) . . . . ? C10 C9 C13 C12 2.2(5) . . . . ? C8 C9 C13 C12 -175.3(3) . . . . ? C7 C6 C14 O4 151.3(2) . . . . ? C5 C6 C14 O4 -31.8(4) . . . . ? C7 C6 C14 O3 -29.7(4) . . . . ? C5 C6 C14 O3 147.2(2) . . . . ? N3 C15 C16 C17 0.1(5) . . . . ? C15 C16 C17 C18 -0.5(4) . . . . ? C15 C16 C17 C17 178.5(3) . . . 2_766 ? C16 C17 C18 C19 0.3(4) . . . . ? C17 C17 C18 C19 -178.7(3) 2_766 . . . ? C17 C18 C19 N3 0.5(5) . . . . ? O5 C8 N1 C4 6.5(5) . . . . ? C9 C8 N1 C4 -173.4(2) . . . . ? C3 C4 N1 C8 177.4(3) . . . . ? C5 C4 N1 C8 -1.9(4) . . . . ? C10 C11 N2 C12 2.6(4) . . . . ? C10 C11 N2 Co1 -168.1(2) . . . 1_666 ? C13 C12 N2 C11 -3.8(5) . . . . ? C13 C12 N2 Co1 168.2(3) . . . 1_666 ? C18 C19 N3 C15 -0.9(4) . . . . ? C18 C19 N3 Co1 169.2(2) . . . . ? C16 C15 N3 C19 0.6(4) . . . . ? C16 C15 N3 Co1 -169.5(2) . . . . ? O1 Co1 N3 C19 -74.0(2) . . . . ? O4 Co1 N3 C19 158.2(2) 1_545 . . . ? O3 Co1 N3 C19 37.1(2) 2_665 . . . ? N2 Co1 N3 C19 -27.1(7) 1_444 . . . ? O1 Co1 N3 C15 95.6(2) . . . . ? O4 Co1 N3 C15 -32.3(2) 1_545 . . . ? O3 Co1 N3 C15 -153.3(2) 2_665 . . . ? N2 Co1 N3 C15 142.5(6) 1_444 . . . ? O2 C1 O1 Co1 -59.9(3) . . . . ? C2 C1 O1 Co1 118.9(2) . . . . ? O4 Co1 O1 C1 54.3(2) 1_545 . . . ? O3 Co1 O1 C1 -119.3(2) 2_665 . . . ? N2 Co1 O1 C1 153.5(2) 1_444 . . . ? N3 Co1 O1 C1 -32.2(2) . . . . ? O4 C14 O3 Co1 53.2(4) . . . 2_665 ? C6 C14 O3 Co1 -125.7(2) . . . 2_665 ? O3 C14 O4 Co1 -1.6(5) . . . 1_565 ? C6 C14 O4 Co1 177.27(18) . . . 1_565 ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.334 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.067 data_5 _database_code_depnum_ccdc_archive 'CCDC 751971' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 Co N4 O7' _chemical_formula_weight 447.27 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 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.698(5) _cell_length_b 17.961(12) _cell_length_c 12.777(9) _cell_angle_alpha 90.00 _cell_angle_beta 102.005(9) _cell_angle_gamma 90.00 _cell_volume 1728(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.719 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 916 _exptl_absorpt_coefficient_mu 1.047 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.860 _exptl_absorpt_correction_T_max 0.901 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _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 8535 _diffrn_reflns_av_R_equivalents 0.0887 _diffrn_reflns_av_sigmaI/netI 0.0807 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3033 _reflns_number_gt 2529 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0894P)^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 3033 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1362 _refine_ls_wR_factor_gt 0.1317 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.003 _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 N4 N 0.0160(5) 0.3378(2) 0.7770(3) 0.0599(10) Uani 1 1 d . . . H4 H -0.0073 0.3349 0.8399 0.072 Uiso 1 1 calc R . . C16 C -0.1014(4) 0.3343(2) 0.6818(3) 0.0339(9) Uani 1 1 d . . . H16 H -0.2232 0.3270 0.6725 0.041 Uiso 1 1 calc R . . N2 N 1.2018(4) 0.38643(16) 1.4107(2) 0.0246(6) Uani 1 1 d . . . C12 C 1.1101(6) 0.4482(2) 1.3892(3) 0.0434(10) Uani 1 1 d . . . H12 H 1.1160 0.4830 1.4437 0.052 Uiso 1 1 calc R . . C11 C 1.1902(5) 0.3371(2) 1.3317(3) 0.0373(9) Uani 1 1 d . . . H11 H 1.2539 0.2930 1.3451 0.045 Uiso 1 1 calc R . . C10 C 1.0877(5) 0.3487(2) 1.2305(3) 0.0361(9) Uani 1 1 d . . . H10 H 1.0827 0.3126 1.1778 0.043 Uiso 1 1 calc R . . O1W O 0.5901(3) 0.38173(13) 0.49068(18) 0.0310(6) Uani 1 1 d . . . H1WB H 0.5762 0.4198 0.4502 0.037 Uiso 1 1 d R . . H1WA H 0.6101 0.3439 0.4551 0.037 Uiso 1 1 d R . . C15 C 0.1792(5) 0.3468(2) 0.7520(3) 0.0295(8) Uani 1 1 d . . . H15 H 0.2866 0.3497 0.8012 0.035 Uiso 1 1 calc R . . O4 O 0.6123(3) 0.75169(13) 0.95961(18) 0.0327(6) Uani 1 1 d . . . C14 C 0.5219(4) 0.71228(19) 0.8863(2) 0.0254(7) Uani 1 1 d . . . Co1 Co 0.36891(5) 0.36413(2) 0.56203(3) 0.02099(19) Uani 1 1 d . . . O1 O 0.5347(3) 0.39534(13) 0.70925(17) 0.0303(6) Uani 1 1 d . . . O2 O 0.3896(3) 0.48734(13) 0.61928(17) 0.0310(6) Uani 1 1 d . . . N1 N 0.8320(4) 0.49586(16) 1.0717(2) 0.0280(7) Uani 1 1 d . . . H1 H 0.8669 0.5282 1.1212 0.034 Uiso 1 1 calc R . . N3 N 0.1592(4) 0.35098(16) 0.6426(2) 0.0285(7) Uani 1 1 d . . . O5 O 0.8613(4) 0.37382(15) 1.0324(2) 0.0425(7) Uani 1 1 d . . . C6 C 0.5670(4) 0.63008(17) 0.8871(2) 0.0213(7) Uani 1 1 d . . . O3 O 0.4012(4) 0.73604(14) 0.8155(2) 0.0484(8) Uani 1 1 d . . . C3 C 0.6610(4) 0.47989(18) 0.8870(2) 0.0243(7) Uani 1 1 d . . . H3 H 0.6923 0.4299 0.8865 0.029 Uiso 1 1 calc R . . C5 C 0.6790(4) 0.59894(18) 0.9745(2) 0.0227(7) Uani 1 1 d . . . H5 H 0.7257 0.6288 1.0332 0.027 Uiso 1 1 calc R . . C7 C 0.5001(4) 0.58535(17) 0.7986(2) 0.0223(7) Uani 1 1 d . . . H7 H 0.4212 0.6051 0.7401 0.027 Uiso 1 1 calc R . . C4 C 0.7236(4) 0.52377(18) 0.9767(2) 0.0224(7) Uani 1 1 d . . . C2 C 0.5511(4) 0.51169(18) 0.7980(2) 0.0212(7) Uani 1 1 d . . . O2W O 0.2819(5) 0.76268(18) 0.0998(2) 0.0658(10) Uani 1 1 d . . . H2WA H 0.3155 0.7565 0.1669 0.079 Uiso 1 1 d R . . H2WB H 0.2449 0.7213 0.0714 0.079 Uiso 1 1 d R . . C8 C 0.8884(4) 0.42530(18) 1.0957(3) 0.0254(7) Uani 1 1 d . . . C1 C 0.4888(4) 0.46217(19) 0.7026(2) 0.0243(7) Uani 1 1 d . . . C9 C 0.9934(4) 0.41372(18) 1.2080(2) 0.0239(7) Uani 1 1 d . . . C13 C 1.0052(6) 0.4646(2) 1.2902(3) 0.0474(11) Uani 1 1 d . . . H13 H 0.9433 0.5093 1.2791 0.057 Uiso 1 1 calc R . . C17 C -0.0120(5) 0.3432(3) 0.6041(3) 0.0425(10) Uani 1 1 d . . . H17 H -0.0641 0.3438 0.5316 0.051 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 N4 0.064(3) 0.072(3) 0.046(2) 0.003(2) 0.0160(19) -0.005(2) C16 0.0121(16) 0.064(3) 0.0240(18) -0.0032(17) 0.0001(13) -0.0081(16) N2 0.0272(15) 0.0248(15) 0.0190(14) 0.0030(11) -0.0013(11) 0.0025(12) C12 0.064(3) 0.038(2) 0.0206(18) -0.0081(15) -0.0089(17) 0.020(2) C11 0.051(2) 0.027(2) 0.0261(19) -0.0005(15) -0.0094(16) 0.0106(17) C10 0.051(2) 0.027(2) 0.0232(18) -0.0036(14) -0.0088(16) 0.0031(16) O1W 0.0343(14) 0.0299(13) 0.0283(13) 0.0034(10) 0.0055(10) 0.0026(11) C15 0.0273(19) 0.035(2) 0.0256(18) 0.0013(14) 0.0030(14) -0.0043(15) O4 0.0479(15) 0.0168(12) 0.0283(12) -0.0040(10) -0.0039(11) -0.0024(10) C14 0.0330(19) 0.0214(17) 0.0202(16) -0.0003(13) 0.0019(14) 0.0016(14) Co1 0.0260(3) 0.0199(3) 0.0145(3) 0.00043(15) -0.00188(18) -0.00025(16) O1 0.0328(13) 0.0235(14) 0.0304(13) -0.0096(10) -0.0029(10) 0.0003(10) O2 0.0421(14) 0.0269(13) 0.0183(12) -0.0009(9) -0.0069(10) -0.0039(11) N1 0.0380(17) 0.0254(16) 0.0152(13) -0.0006(11) -0.0067(11) 0.0043(12) N3 0.0296(16) 0.0316(17) 0.0230(15) -0.0008(12) 0.0026(12) -0.0026(12) O5 0.0619(19) 0.0290(15) 0.0265(13) -0.0035(11) -0.0139(12) 0.0101(12) C6 0.0244(17) 0.0206(17) 0.0185(16) 0.0002(12) 0.0039(13) 0.0007(12) O3 0.0610(19) 0.0273(15) 0.0443(16) -0.0004(12) -0.0175(14) 0.0122(13) C3 0.0314(18) 0.0192(17) 0.0203(16) -0.0006(13) 0.0010(13) 0.0009(14) C5 0.0280(17) 0.0222(18) 0.0164(15) -0.0016(13) 0.0011(12) -0.0019(13) C7 0.0245(17) 0.0199(17) 0.0196(16) 0.0020(13) -0.0019(12) -0.0003(13) C4 0.0246(17) 0.0251(18) 0.0163(15) 0.0022(12) 0.0014(12) 0.0016(13) C2 0.0215(17) 0.0229(17) 0.0172(15) -0.0040(12) -0.0004(12) -0.0035(13) O2W 0.096(3) 0.059(2) 0.0404(17) 0.0036(14) 0.0097(17) -0.0297(18) C8 0.0255(18) 0.0248(19) 0.0234(16) 0.0013(14) -0.0007(13) 0.0021(13) C1 0.0253(17) 0.0253(19) 0.0215(17) -0.0022(14) 0.0033(13) -0.0041(14) C9 0.0261(17) 0.0258(18) 0.0176(16) 0.0035(13) -0.0005(12) -0.0004(14) C13 0.067(3) 0.038(2) 0.029(2) -0.0029(17) -0.0091(18) 0.029(2) C17 0.032(2) 0.063(3) 0.028(2) -0.0011(18) -0.0042(16) -0.0049(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N4 C16 1.357(5) . ? N4 C15 1.368(5) . ? N4 H4 0.8600 . ? C16 C17 1.330(5) . ? C16 H16 0.9300 . ? N2 C12 1.314(5) . ? N2 C11 1.331(4) . ? N2 Co1 2.126(3) 1_656 ? C12 C13 1.383(5) . ? C12 H12 0.9300 . ? C11 C10 1.383(5) . ? C11 H11 0.9300 . ? C10 C9 1.373(5) . ? C10 H10 0.9300 . ? O1W Co1 2.116(3) . ? O1W H1WB 0.8501 . ? O1W H1WA 0.8500 . ? C15 N3 1.376(4) . ? C15 H15 0.9300 . ? O4 C14 1.261(4) . ? O4 Co1 2.047(3) 2_656 ? C14 O3 1.230(4) . ? C14 C6 1.516(5) . ? Co1 O4 2.047(3) 2_646 ? Co1 N3 2.101(3) . ? Co1 O1 2.117(2) . ? Co1 N2 2.126(3) 1_454 ? Co1 O2 2.326(3) . ? O1 C1 1.249(4) . ? O2 C1 1.258(4) . ? N1 C8 1.354(4) . ? N1 C4 1.414(4) . ? N1 H1 0.8600 . ? N3 C17 1.314(5) . ? O5 C8 1.217(4) . ? C6 C5 1.380(5) . ? C6 C7 1.395(4) . ? C3 C2 1.391(4) . ? C3 C4 1.392(4) . ? C3 H3 0.9300 . ? C5 C4 1.392(5) . ? C5 H5 0.9300 . ? C7 C2 1.380(4) . ? C7 H7 0.9300 . ? C2 C1 1.505(4) . ? O2W H2WA 0.8501 . ? O2W H2WB 0.8500 . ? C8 C9 1.508(4) . ? C9 C13 1.380(5) . ? C13 H13 0.9300 . ? C17 H17 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 C16 N4 C15 105.6(3) . . ? C16 N4 H4 127.2 . . ? C15 N4 H4 127.2 . . ? C17 C16 N4 108.2(3) . . ? C17 C16 H16 125.9 . . ? N4 C16 H16 125.9 . . ? C12 N2 C11 117.0(3) . . ? C12 N2 Co1 123.1(2) . 1_656 ? C11 N2 Co1 119.8(2) . 1_656 ? N2 C12 C13 123.8(3) . . ? N2 C12 H12 118.1 . . ? C13 C12 H12 118.1 . . ? N2 C11 C10 123.0(3) . . ? N2 C11 H11 118.5 . . ? C10 C11 H11 118.5 . . ? C9 C10 C11 119.8(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? Co1 O1W H1WB 111.8 . . ? Co1 O1W H1WA 111.2 . . ? H1WB O1W H1WA 109.4 . . ? N3 C15 N4 109.2(3) . . ? N3 C15 H15 125.4 . . ? N4 C15 H15 125.4 . . ? C14 O4 Co1 119.8(2) . 2_656 ? O3 C14 O4 124.5(3) . . ? O3 C14 C6 118.6(3) . . ? O4 C14 C6 116.8(3) . . ? O4 Co1 N3 92.20(11) 2_646 . ? O4 Co1 O1W 90.20(10) 2_646 . ? N3 Co1 O1W 175.82(10) . . ? O4 Co1 O1 109.56(9) 2_646 . ? N3 Co1 O1 88.67(11) . . ? O1W Co1 O1 87.30(10) . . ? O4 Co1 N2 96.27(10) 2_646 1_454 ? N3 Co1 N2 94.93(12) . 1_454 ? O1W Co1 N2 88.21(11) . 1_454 ? O1 Co1 N2 153.78(11) . 1_454 ? O4 Co1 O2 168.18(8) 2_646 . ? N3 Co1 O2 87.83(10) . . ? O1W Co1 O2 89.12(9) . . ? O1 Co1 O2 58.63(8) . . ? N2 Co1 O2 95.49(10) 1_454 . ? C1 O1 Co1 94.85(19) . . ? C1 O2 Co1 85.07(19) . . ? C8 N1 C4 129.1(3) . . ? C8 N1 H1 115.5 . . ? C4 N1 H1 115.5 . . ? C17 N3 C15 105.5(3) . . ? C17 N3 Co1 129.8(3) . . ? C15 N3 Co1 124.7(2) . . ? C5 C6 C7 119.1(3) . . ? C5 C6 C14 120.2(3) . . ? C7 C6 C14 120.7(3) . . ? C2 C3 C4 119.2(3) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C6 C5 C4 121.3(3) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C2 C7 C6 120.0(3) . . ? C2 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C5 C4 C3 119.4(3) . . ? C5 C4 N1 117.4(3) . . ? C3 C4 N1 123.2(3) . . ? C7 C2 C3 120.9(3) . . ? C7 C2 C1 121.9(3) . . ? C3 C2 C1 117.2(3) . . ? H2WA O2W H2WB 108.7 . . ? O5 C8 N1 123.9(3) . . ? O5 C8 C9 120.7(3) . . ? N1 C8 C9 115.3(3) . . ? O1 C1 O2 121.1(3) . . ? O1 C1 C2 118.4(3) . . ? O2 C1 C2 120.5(3) . . ? C10 C9 C13 117.1(3) . . ? C10 C9 C8 118.2(3) . . ? C13 C9 C8 124.8(3) . . ? C12 C13 C9 119.3(3) . . ? C12 C13 H13 120.4 . . ? C9 C13 H13 120.4 . . ? N3 C17 C16 111.5(3) . . ? N3 C17 H17 124.2 . . ? C16 C17 H17 124.2 . . ? 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 C15 N4 C16 C17 -1.8(5) . . . . ? C11 N2 C12 C13 -0.6(6) . . . . ? Co1 N2 C12 C13 177.9(3) 1_656 . . . ? C12 N2 C11 C10 0.1(6) . . . . ? Co1 N2 C11 C10 -178.4(3) 1_656 . . . ? N2 C11 C10 C9 0.5(6) . . . . ? C16 N4 C15 N3 1.8(4) . . . . ? Co1 O4 C14 O3 -22.8(5) 2_656 . . . ? Co1 O4 C14 C6 157.3(2) 2_656 . . . ? O4 Co1 O1 C1 -176.56(19) 2_646 . . . ? N3 Co1 O1 C1 -84.7(2) . . . . ? O1W Co1 O1 C1 94.2(2) . . . . ? N2 Co1 O1 C1 13.8(3) 1_454 . . . ? O2 Co1 O1 C1 3.57(18) . . . . ? O4 Co1 O2 C1 -4.1(6) 2_646 . . . ? N3 Co1 O2 C1 86.2(2) . . . . ? O1W Co1 O2 C1 -90.9(2) . . . . ? O1 Co1 O2 C1 -3.54(18) . . . . ? N2 Co1 O2 C1 -179.03(19) 1_454 . . . ? N4 C15 N3 C17 -1.1(4) . . . . ? N4 C15 N3 Co1 -179.6(3) . . . . ? O4 Co1 N3 C17 -83.5(3) 2_646 . . . ? O1W Co1 N3 C17 151.5(13) . . . . ? O1 Co1 N3 C17 167.0(4) . . . . ? N2 Co1 N3 C17 13.0(4) 1_454 . . . ? O2 Co1 N3 C17 108.3(3) . . . . ? O4 Co1 N3 C15 94.6(3) 2_646 . . . ? O1W Co1 N3 C15 -30.4(15) . . . . ? O1 Co1 N3 C15 -14.9(3) . . . . ? N2 Co1 N3 C15 -168.9(3) 1_454 . . . ? O2 Co1 N3 C15 -73.6(3) . . . . ? O3 C14 C6 C5 -168.7(3) . . . . ? O4 C14 C6 C5 11.1(5) . . . . ? O3 C14 C6 C7 13.1(5) . . . . ? O4 C14 C6 C7 -167.1(3) . . . . ? C7 C6 C5 C4 -1.2(5) . . . . ? C14 C6 C5 C4 -179.4(3) . . . . ? C5 C6 C7 C2 -2.2(5) . . . . ? C14 C6 C7 C2 176.0(3) . . . . ? C6 C5 C4 C3 3.2(5) . . . . ? C6 C5 C4 N1 -176.8(3) . . . . ? C2 C3 C4 C5 -1.8(5) . . . . ? C2 C3 C4 N1 178.2(3) . . . . ? C8 N1 C4 C5 177.4(3) . . . . ? C8 N1 C4 C3 -2.6(5) . . . . ? C6 C7 C2 C3 3.6(5) . . . . ? C6 C7 C2 C1 -177.3(3) . . . . ? C4 C3 C2 C7 -1.6(5) . . . . ? C4 C3 C2 C1 179.3(3) . . . . ? C4 N1 C8 O5 5.2(6) . . . . ? C4 N1 C8 C9 -176.1(3) . . . . ? Co1 O1 C1 O2 -6.6(3) . . . . ? Co1 O1 C1 C2 171.8(2) . . . . ? Co1 O2 C1 O1 6.0(3) . . . . ? Co1 O2 C1 C2 -172.4(3) . . . . ? C7 C2 C1 O1 -177.3(3) . . . . ? C3 C2 C1 O1 1.9(5) . . . . ? C7 C2 C1 O2 1.1(5) . . . . ? C3 C2 C1 O2 -179.7(3) . . . . ? C11 C10 C9 C13 -0.7(6) . . . . ? C11 C10 C9 C8 177.9(3) . . . . ? O5 C8 C9 C10 13.2(5) . . . . ? N1 C8 C9 C10 -165.6(3) . . . . ? O5 C8 C9 C13 -168.3(4) . . . . ? N1 C8 C9 C13 12.9(5) . . . . ? N2 C12 C13 C9 0.3(7) . . . . ? C10 C9 C13 C12 0.3(6) . . . . ? C8 C9 C13 C12 -178.2(4) . . . . ? C15 N3 C17 C16 -0.1(5) . . . . ? Co1 N3 C17 C16 178.3(3) . . . . ? N4 C16 C17 N3 1.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.458 _refine_diff_density_min -0.935 _refine_diff_density_rms 0.166 data_6 _database_code_depnum_ccdc_archive 'CCDC 751972' _audit_creation_date 2008-08-14 _audit_creation_method SHELXL-97 _publ_section_references ; Rigaku Americas and Rigaku Corporation. (2007). CrystalStructure (Version 3.8). Single Crystal Structure Analysis Software. Rigaku Americas, 9009 TX, USA 77381-5209. Rigaku, Tokyo 196-8666, Japan. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M., Polidori, G., and Camalli, M. (1994) J. Appl. Cryst., 27, 435. SIR92 Sheldrick, G.M. (1997). SHELXL97. University of Gottingen, Germany. ; _chemical_name_systematic ; [Cu(M4)(Im)(H2O)]-H2O ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H16 Cu N4 O7' _chemical_formula_sum 'C17 H16 Cu N4 O7' _chemical_formula_weight 451.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.435(3) _cell_length_b 18.746(5) _cell_length_c 12.541(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.762(14) _cell_angle_gamma 90.00 _cell_volume 1711.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 200 _cell_measurement_reflns_used 11374 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description column _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.754 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 924 _exptl_absorpt_coefficient_mu 1.330 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.686 _exptl_absorpt_correction_T_max 0.819 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _diffrn_ambient_temperature 200 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 15973 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3917 _reflns_number_gt 3499 _reflns_threshold_expression I>2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0274P)^2^+2.2419P] 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 3917 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0765 _refine_ls_wR_factor_gt 0.0739 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 Cu1 Cu 0.69719(3) 0.362189(12) 0.431217(18) 0.01618(8) Uani 1 1 d . . . O1 O 0.2027(2) 0.37997(8) -0.02346(12) 0.0289(4) Uani 1 1 d . . . O2 O 0.4817(2) 0.36709(9) 0.49795(12) 0.0212(3) Uani 1 1 d . . . H2 H 0.455(4) 0.3314(15) 0.524(2) 0.025 Uiso 1 1 d . . . H3 H 0.464(4) 0.4011(15) 0.533(2) 0.025 Uiso 1 1 d . . . O3 O 0.3457(3) 0.25529(10) 0.58594(15) 0.0360(4) Uani 1 1 d . . . H4 H 0.342(4) 0.2131(18) 0.553(2) 0.043 Uiso 1 1 d . . . H5 H 0.408(4) 0.2472(16) 0.645(3) 0.043 Uiso 1 1 d . . . O31 O 0.5585(2) 0.41947(7) 0.30693(11) 0.0213(3) Uani 1 1 d . . . O32 O 0.6259(2) 0.51880(8) 0.40383(11) 0.0251(3) Uani 1 1 d . . . O52 O 0.4983(2) 0.75436(8) 0.20030(12) 0.0301(4) Uani 1 1 d . . . O51 O 0.2970(2) 0.75128(7) 0.04358(12) 0.0223(3) Uani 1 1 d . . . N1 N 0.1882(3) 0.49860(9) -0.06037(14) 0.0214(4) Uani 1 1 d . . . N11 N -0.1303(2) 0.38597(9) -0.41402(13) 0.0191(3) Uani 1 1 d . . . H1 H 0.149(4) 0.5266(14) -0.104(2) 0.023 Uiso 1 1 d . . . N21 N 0.9001(2) 0.35537(9) 0.35328(14) 0.0197(3) Uani 1 1 d . . . N22 N 1.1699(3) 0.34874(12) 0.31032(16) 0.0325(5) Uani 1 1 d . . . H14 H 1.2901 0.3486 0.3174 0.039 Uiso 1 1 calc R . . C1 C 0.2845(3) 0.53011(10) 0.03734(15) 0.0165(4) Uani 1 1 d . . . C2 C 0.3711(3) 0.49168(10) 0.12815(15) 0.0168(4) Uani 1 1 d . . . H6 H 0.3665 0.4410 0.1280 0.020 Uiso 1 1 calc R . . C3 C 0.4648(3) 0.52839(10) 0.21942(15) 0.0147(4) Uani 1 1 d . . . C4 C 0.4763(3) 0.60254(10) 0.21911(15) 0.0161(4) Uani 1 1 d . . . H7 H 0.5439 0.6269 0.2808 0.019 Uiso 1 1 calc R . . C5 C 0.3886(3) 0.64088(10) 0.12837(15) 0.0159(4) Uani 1 1 d . . . C11 C 0.1564(3) 0.42933(10) -0.08685(15) 0.0178(4) Uani 1 1 d . . . C12 C -0.0659(5) 0.33492(13) -0.3439(2) 0.0533(9) Uani 1 1 d . . . H9 H -0.0842 0.2868 -0.3674 0.064 Uiso 1 1 calc R . . C13 C 0.0264(5) 0.34762(13) -0.2386(2) 0.0516(9) Uani 1 1 d . . . H10 H 0.0694 0.3088 -0.1915 0.062 Uiso 1 1 calc R . . C14 C 0.0559(3) 0.41612(10) -0.20241(15) 0.0169(4) Uani 1 1 d . . . C15 C -0.0106(4) 0.46910(13) -0.2747(2) 0.0446(8) Uani 1 1 d . . . H11 H 0.0060 0.5177 -0.2534 0.054 Uiso 1 1 calc R . . C16 C -0.1023(4) 0.45178(12) -0.37925(19) 0.0396(7) Uani 1 1 d . . . H12 H -0.1470 0.4895 -0.4281 0.048 Uiso 1 1 calc R . . C21 C 1.0783(3) 0.35684(13) 0.39097(18) 0.0298(5) Uani 1 1 d . . . H13 H 1.1346 0.3629 0.4655 0.036 Uiso 1 1 calc R . . C22 C 1.0442(3) 0.34077(12) 0.21525(18) 0.0254(4) Uani 1 1 d . . . H15 H 1.0687 0.3338 0.1446 0.030 Uiso 1 1 calc R . . C23 C 0.8772(3) 0.34482(11) 0.24241(16) 0.0218(4) Uani 1 1 d . . . H16 H 0.7625 0.3410 0.1929 0.026 Uiso 1 1 calc R . . C31 C 0.5567(3) 0.48674(10) 0.31844(15) 0.0162(4) Uani 1 1 d . . . C51 C 0.3965(3) 0.72154(10) 0.12501(15) 0.0180(4) Uani 1 1 d . . . C6 C 0.2919(3) 0.60434(10) 0.03885(15) 0.0172(4) Uani 1 1 d . . . H8 H 0.2295 0.6304 -0.0227 0.021 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 0.01886(13) 0.01624(13) 0.01179(12) 0.00236(8) -0.00079(9) 0.00159(9) O1 0.0460(10) 0.0177(7) 0.0167(7) 0.0018(6) -0.0085(7) -0.0010(7) O2 0.0256(8) 0.0185(7) 0.0195(7) -0.0012(6) 0.0046(6) -0.0007(6) O3 0.0522(12) 0.0311(9) 0.0221(8) 0.0014(7) 0.0014(8) -0.0130(8) O31 0.0303(8) 0.0148(7) 0.0157(7) 0.0028(5) -0.0024(6) 0.0057(6) O32 0.0366(9) 0.0201(7) 0.0135(7) -0.0004(5) -0.0068(6) 0.0060(6) O52 0.0457(10) 0.0163(7) 0.0217(8) -0.0009(6) -0.0087(7) -0.0053(7) O51 0.0333(8) 0.0122(7) 0.0183(7) 0.0026(5) -0.0024(6) 0.0009(6) N1 0.0330(10) 0.0143(8) 0.0116(8) 0.0010(6) -0.0076(7) 0.0004(7) N11 0.0239(9) 0.0182(8) 0.0129(8) -0.0015(6) -0.0020(7) -0.0011(7) N21 0.0214(9) 0.0215(9) 0.0149(8) 0.0028(6) 0.0005(7) 0.0009(7) N22 0.0191(9) 0.0530(13) 0.0243(10) 0.0006(9) 0.0017(8) 0.0065(9) C1 0.0206(10) 0.0167(9) 0.0108(8) -0.0015(7) -0.0004(7) -0.0012(7) C2 0.0219(10) 0.0130(9) 0.0142(9) 0.0011(7) 0.0004(7) 0.0008(7) C3 0.0170(9) 0.0155(9) 0.0109(8) 0.0019(7) 0.0012(7) 0.0024(7) C4 0.0199(9) 0.0160(9) 0.0112(8) -0.0009(7) 0.0003(7) 0.0006(7) C5 0.0212(10) 0.0119(8) 0.0140(9) 0.0010(7) 0.0024(7) -0.0005(7) C11 0.0217(10) 0.0172(9) 0.0133(9) -0.0016(7) 0.0012(7) -0.0010(7) C12 0.103(3) 0.0138(11) 0.0252(13) -0.0045(9) -0.0297(15) 0.0042(13) C13 0.098(3) 0.0163(11) 0.0234(12) 0.0003(9) -0.0281(14) 0.0019(13) C14 0.0188(9) 0.0179(9) 0.0128(9) -0.0016(7) 0.0007(7) -0.0004(7) C15 0.081(2) 0.0153(11) 0.0235(12) -0.0004(9) -0.0215(13) -0.0088(12) C16 0.0699(19) 0.0169(11) 0.0201(11) 0.0029(8) -0.0188(12) -0.0061(11) C21 0.0243(11) 0.0449(14) 0.0182(10) 0.0015(9) -0.0003(9) 0.0039(10) C22 0.0291(12) 0.0281(11) 0.0186(10) -0.0009(8) 0.0041(9) 0.0025(9) C23 0.0239(10) 0.0237(10) 0.0158(9) 0.0001(8) -0.0005(8) -0.0018(8) C31 0.0172(9) 0.0175(9) 0.0130(9) 0.0028(7) 0.0012(7) 0.0037(7) C51 0.0257(10) 0.0138(9) 0.0139(9) 0.0002(7) 0.0028(8) 0.0006(8) C6 0.0221(10) 0.0163(9) 0.0113(8) 0.0029(7) -0.0014(7) 0.0027(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 Cu1 O2 1.9550(17) . ? Cu1 N21 1.9617(19) . ? Cu1 O31 1.9975(14) . ? Cu1 O51 2.1022(15) 2_645 ? Cu1 N11 2.1438(17) 1_656 ? O1 C11 1.223(2) . ? O2 H2 0.79(3) . ? O2 H3 0.80(3) . ? O3 H4 0.89(3) . ? O3 H5 0.80(3) . ? O31 C31 1.270(2) . ? O32 C31 1.244(2) . ? O52 C51 1.246(2) . ? O51 C51 1.262(2) . ? O51 Cu1 2.1022(15) 2_655 ? N1 C11 1.349(3) . ? N1 C1 1.416(2) . ? N1 H1 0.77(3) . ? N11 C16 1.311(3) . ? N11 C12 1.321(3) . ? N11 Cu1 2.1438(17) 1_454 ? N21 C21 1.313(3) . ? N21 C23 1.380(3) . ? N22 C21 1.338(3) . ? N22 C22 1.365(3) . ? N22 H14 0.8800 . ? C1 C2 1.390(3) . ? C1 C6 1.393(3) . ? C2 C3 1.394(3) . ? C2 H6 0.9500 . ? C3 C4 1.393(3) . ? C3 C31 1.507(2) . ? C4 C5 1.391(3) . ? C4 H7 0.9500 . ? C5 C6 1.385(3) . ? C5 C51 1.514(3) . ? C11 C14 1.509(3) . ? C12 C13 1.379(3) . ? C12 H9 0.9500 . ? C13 C14 1.365(3) . ? C13 H10 0.9500 . ? C14 C15 1.367(3) . ? C15 C16 1.388(3) . ? C15 H11 0.9500 . ? C16 H12 0.9500 . ? C21 H13 0.9500 . ? C22 C23 1.355(3) . ? C22 H15 0.9500 . ? C23 H16 0.9500 . ? C6 H8 0.9500 . ? 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 N21 175.43(7) . . ? O2 Cu1 O31 88.35(7) . . ? N21 Cu1 O31 88.47(7) . . ? O2 Cu1 O51 88.60(6) . 2_645 ? N21 Cu1 O51 90.92(7) . 2_645 ? O31 Cu1 O51 129.83(6) . 2_645 ? O2 Cu1 N11 89.66(7) . 1_656 ? N21 Cu1 N11 94.91(7) . 1_656 ? O31 Cu1 N11 135.48(6) . 1_656 ? O51 Cu1 N11 94.55(6) 2_645 1_656 ? Cu1 O2 H2 115.8(19) . . ? Cu1 O2 H3 120.7(19) . . ? H2 O2 H3 112(3) . . ? H4 O3 H5 103(3) . . ? C31 O31 Cu1 117.46(12) . . ? C51 O51 Cu1 108.93(12) . 2_655 ? C11 N1 C1 130.30(17) . . ? C11 N1 H1 117.4(19) . . ? C1 N1 H1 112.3(19) . . ? C16 N11 C12 116.67(19) . . ? C16 N11 Cu1 121.46(14) . 1_454 ? C12 N11 Cu1 121.36(15) . 1_454 ? C21 N21 C23 105.87(18) . . ? C21 N21 Cu1 129.88(15) . . ? C23 N21 Cu1 124.20(15) . . ? C21 N22 C22 108.0(2) . . ? C21 N22 H14 126.0 . . ? C22 N22 H14 126.0 . . ? C2 C1 C6 119.76(17) . . ? C2 C1 N1 124.11(18) . . ? C6 C1 N1 116.12(17) . . ? C1 C2 C3 119.16(18) . . ? C1 C2 H6 120.4 . . ? C3 C2 H6 120.4 . . ? C4 C3 C2 120.73(17) . . ? C4 C3 C31 120.11(17) . . ? C2 C3 C31 119.16(17) . . ? C5 C4 C3 119.96(17) . . ? C5 C4 H7 120.0 . . ? C3 C4 H7 120.0 . . ? C6 C5 C4 119.15(17) . . ? C6 C5 C51 119.21(17) . . ? C4 C5 C51 121.64(17) . . ? O1 C11 N1 123.80(18) . . ? O1 C11 C14 121.24(18) . . ? N1 C11 C14 114.96(17) . . ? N11 C12 C13 123.6(2) . . ? N11 C12 H9 118.2 . . ? C13 C12 H9 118.2 . . ? C14 C13 C12 119.7(2) . . ? C14 C13 H10 120.1 . . ? C12 C13 H10 120.1 . . ? C13 C14 C15 116.80(19) . . ? C13 C14 C11 119.24(18) . . ? C15 C14 C11 123.96(18) . . ? C14 C15 C16 119.9(2) . . ? C14 C15 H11 120.1 . . ? C16 C15 H11 120.1 . . ? N11 C16 C15 123.3(2) . . ? N11 C16 H12 118.4 . . ? C15 C16 H12 118.4 . . ? N21 C21 N22 110.9(2) . . ? N21 C21 H13 124.5 . . ? N22 C21 H13 124.5 . . ? C23 C22 N22 105.88(19) . . ? C23 C22 H15 127.1 . . ? N22 C22 H15 127.1 . . ? C22 C23 N21 109.30(19) . . ? C22 C23 H16 125.4 . . ? N21 C23 H16 125.4 . . ? O32 C31 O31 124.43(17) . . ? O32 C31 C3 119.81(17) . . ? O31 C31 C3 115.75(16) . . ? O52 C51 O51 124.10(18) . . ? O52 C51 C5 119.55(17) . . ? O51 C51 C5 116.35(17) . . ? C5 C6 C1 121.19(17) . . ? C5 C6 H8 119.4 . . ? C1 C6 H8 119.4 . . ? 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 Cu1 O31 C31 82.81(15) . . . . ? N21 Cu1 O31 C31 -100.46(15) . . . . ? O51 Cu1 O31 C31 169.61(13) 2_645 . . . ? N11 Cu1 O31 C31 -5.02(19) 1_656 . . . ? O31 Cu1 N21 C21 142.6(2) . . . . ? O51 Cu1 N21 C21 -87.6(2) 2_645 . . . ? N11 Cu1 N21 C21 7.0(2) 1_656 . . . ? O31 Cu1 N21 C23 -40.15(16) . . . . ? O51 Cu1 N21 C23 89.67(16) 2_645 . . . ? N11 Cu1 N21 C23 -175.68(16) 1_656 . . . ? C11 N1 C1 C2 1.3(4) . . . . ? C11 N1 C1 C6 -179.7(2) . . . . ? C6 C1 C2 C3 -0.2(3) . . . . ? N1 C1 C2 C3 178.85(19) . . . . ? C1 C2 C3 C4 -1.7(3) . . . . ? C1 C2 C3 C31 179.20(18) . . . . ? C2 C3 C4 C5 2.1(3) . . . . ? C31 C3 C4 C5 -178.86(18) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C3 C4 C5 C51 179.55(18) . . . . ? C1 N1 C11 O1 3.7(4) . . . . ? C1 N1 C11 C14 -176.8(2) . . . . ? C16 N11 C12 C13 0.2(5) . . . . ? Cu1 N11 C12 C13 -171.8(3) 1_454 . . . ? N11 C12 C13 C14 -0.3(6) . . . . ? C12 C13 C14 C15 0.3(5) . . . . ? C12 C13 C14 C11 179.7(3) . . . . ? O1 C11 C14 C13 -4.1(3) . . . . ? N1 C11 C14 C13 176.4(3) . . . . ? O1 C11 C14 C15 175.3(3) . . . . ? N1 C11 C14 C15 -4.2(3) . . . . ? C13 C14 C15 C16 -0.2(5) . . . . ? C11 C14 C15 C16 -179.6(3) . . . . ? C12 N11 C16 C15 -0.1(5) . . . . ? Cu1 N11 C16 C15 171.8(2) 1_454 . . . ? C14 C15 C16 N11 0.1(5) . . . . ? C23 N21 C21 N22 0.8(3) . . . . ? Cu1 N21 C21 N22 178.45(16) . . . . ? C22 N22 C21 N21 -0.7(3) . . . . ? C21 N22 C22 C23 0.3(3) . . . . ? N22 C22 C23 N21 0.1(3) . . . . ? C21 N21 C23 C22 -0.6(2) . . . . ? Cu1 N21 C23 C22 -178.40(14) . . . . ? Cu1 O31 C31 O32 -4.4(3) . . . . ? Cu1 O31 C31 C3 174.85(12) . . . . ? C4 C3 C31 O32 7.7(3) . . . . ? C2 C3 C31 O32 -173.29(19) . . . . ? C4 C3 C31 O31 -171.67(18) . . . . ? C2 C3 C31 O31 7.4(3) . . . . ? Cu1 O51 C51 O52 -8.3(3) 2_655 . . . ? Cu1 O51 C51 C5 171.94(14) 2_655 . . . ? C6 C5 C51 O52 -172.7(2) . . . . ? C4 C5 C51 O52 7.3(3) . . . . ? C6 C5 C51 O51 7.1(3) . . . . ? C4 C5 C51 O51 -172.95(19) . . . . ? C4 C5 C6 C1 -1.4(3) . . . . ? C51 C5 C6 C1 178.51(19) . . . . ? C2 C1 C6 C5 1.8(3) . . . . ? N1 C1 C6 C5 -177.32(19) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.465 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.071