# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '- CoCu-allstructures-rev.cif' _audit_update_record ; 2010-03-10 # Formatted by publCIF ; _publ_contact_author_name 'Leroy Cronin' _publ_contact_author_address ; WestCHEM, Department of Chemistry, University of Glasgow, G12 8QQ, UK. ; _publ_contact_author_email l.cronin@chem.gla.ac.uk loop_ _publ_author_name _publ_author_address J.Fielden ; WestCHEM, Department of Chemistry, University of Glasgow, G12 8QQ, UK. ; D.-L.Long ; WestCHEM, Department of Chemistry, University of Glasgow, G12 8QQ, UK. ; M.Speldrich ; Institut fuer Anorganische Chemie, RWTH Aachen University, D-52074, Aachen, Germany. ; P.Koegerler ; Institut fuer Anorganische Chemie, RWTH Aachen University, D-52074, Aachen, Germany. ; L.Cronin ; WestCHEM, Department of Chemistry, University of Glasgow, G12 8QQ, UK. ; data_compound1 _database_code_depnum_ccdc_archive 'CCDC 828952' #TrackingRef '- CoCu-allstructures-rev.cif' _publ_section_exptl_refinement ; The structure was solved by direct methods. All non-H atoms were refined anisotropically. H atoms were included in calculated positions, except those bonded to O1 and O2, which were found by difference Fourier techniques and refined isotropically, with restraints on the bond lengths. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 Co N5 O4, NO3' _chemical_formula_sum 'C18 H22 Co N6 O8' _chemical_formula_weight 509.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)/c 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 9.93450(10) _cell_length_b 7.23980(10) _cell_length_c 30.0756(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.1390(10) _cell_angle_gamma 90.00 _cell_volume 2055.65(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 27899 _cell_measurement_theta_min 1.52 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1052 _exptl_absorpt_coefficient_mu 0.897 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.715 _exptl_absorpt_correction_T_max 0.816 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ? _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15414 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4593 _reflns_number_gt 4178 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material 'SHELXTL (Bruker, 2001)' _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^)+(0.0341P)^2^+2.9431P] 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 4593 _refine_ls_number_parameters 308 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0951 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 Co Co 0.89812(3) 0.22032(4) 0.874875(8) 0.01629(9) Uani 1 1 d . . . N1 N 0.98330(17) 0.1160(2) 0.82445(6) 0.0187(3) Uani 1 1 d . . . N2 N 1.08938(17) 0.1625(2) 0.92821(6) 0.0180(3) Uani 1 1 d . . . N3 N 0.72148(18) 0.2390(2) 0.81216(6) 0.0190(3) Uani 1 1 d . . . N4 N 0.84824(18) 0.3019(2) 0.93624(5) 0.0174(3) Uani 1 1 d . . . N5 N 0.5473(2) 0.8130(3) 0.92730(7) 0.0298(4) Uani 1 1 d . . . O1 O 1.37409(18) 0.4372(2) 0.86207(6) 0.0312(4) Uani 1 1 d . . . O3 O 0.92362(16) 0.5127(2) 0.86722(5) 0.0237(3) Uani 1 1 d . . . O4 O 0.9660(2) 0.5287(3) 0.80053(6) 0.0417(5) Uani 1 1 d . . . O5 O 0.8264(2) 0.7261(2) 0.81661(6) 0.0341(4) Uani 1 1 d . . . C1 C 1.1251(2) 0.0335(3) 0.83283(7) 0.0218(4) Uani 1 1 d . . . H1A H 1.1186 -0.0623 0.8083 0.026 Uiso 1 1 calc R . . C2 C 1.1730(2) -0.0610(3) 0.88083(7) 0.0225(4) Uani 1 1 d . . . H2A H 1.2539 -0.1432 0.8823 0.027 Uiso 1 1 calc R . . H2B H 1.0947 -0.1393 0.8839 0.027 Uiso 1 1 calc R . . C3 C 1.2174(2) 0.0728(3) 0.92248(7) 0.0204(4) Uani 1 1 d . . . H3 H 1.2649 0.0003 0.9514 0.024 Uiso 1 1 calc R . . C4 C 1.3218(2) 0.2187(3) 0.91601(7) 0.0219(4) Uani 1 1 d . . . H4A H 1.3396 0.3103 0.9416 0.026 Uiso 1 1 calc R . . H4B H 1.4130 0.1581 0.9182 0.026 Uiso 1 1 calc R . . C5 C 1.2673(2) 0.3184(3) 0.86928(7) 0.0226(4) Uani 1 1 d . . . H5 H 1.1814 0.3924 0.8682 0.027 Uiso 1 1 calc R . . C6 C 1.2314(2) 0.1808(3) 0.82908(8) 0.0245(4) Uani 1 1 d . . . H6A H 1.3196 0.1193 0.8283 0.029 Uiso 1 1 calc R . . H6B H 1.1919 0.2486 0.7993 0.029 Uiso 1 1 calc R . . C11 C 0.9010(2) 0.1224(3) 0.78268(7) 0.0231(4) Uani 1 1 d . . . H11 H 0.9323 0.0809 0.7576 0.028 Uiso 1 1 calc R . . C12 C 0.7573(2) 0.1948(3) 0.77359(7) 0.0212(4) Uani 1 1 d . . . C13 C 0.6632(2) 0.2071(3) 0.72874(7) 0.0269(5) Uani 1 1 d . . . H13 H 0.6930 0.1800 0.7023 0.032 Uiso 1 1 calc R . . C14 C 0.5244(3) 0.2599(3) 0.72307(8) 0.0292(5) Uani 1 1 d . . . H14 H 0.4575 0.2699 0.6927 0.035 Uiso 1 1 calc R . . C15 C 0.4857(2) 0.2974(3) 0.76231(8) 0.0276(5) Uani 1 1 d . . . H15 H 0.3905 0.3285 0.7595 0.033 Uiso 1 1 calc R . . C16 C 0.5876(2) 0.2893(3) 0.80610(7) 0.0241(4) Uani 1 1 d . . . H16 H 0.5609 0.3209 0.8328 0.029 Uiso 1 1 calc R . . C21 C 1.0818(2) 0.1807(3) 0.96946(7) 0.0195(4) Uani 1 1 d . . . H21 H 1.1581 0.1426 0.9957 0.023 Uiso 1 1 calc R . . C22 C 0.9535(2) 0.2614(3) 0.97598(7) 0.0173(4) Uani 1 1 d . . . C23 C 0.9427(2) 0.2912(3) 1.02030(7) 0.0212(4) Uani 1 1 d . . . H23 H 1.0188 0.2611 1.0475 0.025 Uiso 1 1 calc R . . C24 C 0.8177(2) 0.3663(3) 1.02390(7) 0.0235(4) Uani 1 1 d . . . H24 H 0.8068 0.3883 1.0537 0.028 Uiso 1 1 calc R . . C25 C 0.7098(2) 0.4083(3) 0.98362(7) 0.0251(4) Uani 1 1 d . . . H25 H 0.6233 0.4590 0.9853 0.030 Uiso 1 1 calc R . . C26 C 0.7298(2) 0.3754(3) 0.94046(7) 0.0229(4) Uani 1 1 d . . . H26 H 0.6557 0.4067 0.9128 0.028 Uiso 1 1 calc R . . N6 N 0.90533(19) 0.5893(2) 0.82720(6) 0.0207(3) Uani 1 1 d . . . O7 O 0.6395(3) 0.9225(4) 0.94792(11) 0.0836(10) Uani 1 1 d . . . O6 O 0.4722(3) 0.7205(4) 0.94358(11) 0.0766(9) Uani 1 1 d . . . O8 O 0.5296(3) 0.7974(5) 0.88564(9) 0.0843(9) Uani 1 1 d . . . O2 O 0.81984(17) -0.0423(2) 0.88794(5) 0.0241(3) Uani 1 1 d D . . H2W H 0.808(3) -0.124(4) 0.8688(9) 0.036 Uiso 1 1 d D . . H1W H 0.753(3) -0.059(4) 0.8968(10) 0.036 Uiso 1 1 d D . . H19 H 1.392(3) 0.522(5) 0.8814(10) 0.039(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co 0.01454(14) 0.02028(15) 0.01544(13) 0.00048(9) 0.00668(10) 0.00204(10) N1 0.0171(8) 0.0197(8) 0.0221(8) -0.0021(6) 0.0101(6) 0.0000(6) N2 0.0145(8) 0.0189(8) 0.0215(8) 0.0020(6) 0.0068(6) 0.0011(6) N3 0.0174(8) 0.0237(9) 0.0167(7) -0.0009(6) 0.0062(6) 0.0008(7) N4 0.0177(8) 0.0191(8) 0.0164(7) 0.0006(6) 0.0068(6) 0.0004(6) N5 0.0200(9) 0.0295(10) 0.0385(11) 0.0033(8) 0.0070(8) 0.0045(8) O1 0.0289(9) 0.0302(9) 0.0405(9) -0.0009(8) 0.0198(7) -0.0088(7) O3 0.0318(8) 0.0220(7) 0.0187(7) 0.0018(6) 0.0098(6) -0.0013(6) O4 0.0573(12) 0.0435(11) 0.0391(9) 0.0097(8) 0.0366(9) 0.0145(9) O5 0.0423(10) 0.0289(9) 0.0276(8) 0.0022(7) 0.0057(7) 0.0133(7) C1 0.0185(10) 0.0243(10) 0.0258(10) -0.0041(8) 0.0114(8) 0.0016(8) C2 0.0189(10) 0.0193(10) 0.0311(10) -0.0001(8) 0.0101(8) 0.0023(8) C3 0.0160(9) 0.0206(10) 0.0254(9) 0.0020(8) 0.0075(8) 0.0037(7) C4 0.0166(9) 0.0229(10) 0.0280(10) -0.0011(8) 0.0094(8) 0.0013(8) C5 0.0185(10) 0.0229(10) 0.0305(10) 0.0011(8) 0.0136(8) -0.0007(8) C6 0.0204(10) 0.0302(11) 0.0276(10) -0.0003(9) 0.0141(8) -0.0011(9) C11 0.0236(10) 0.0291(11) 0.0210(9) -0.0036(8) 0.0132(8) -0.0008(8) C12 0.0208(10) 0.0249(10) 0.0193(9) -0.0014(8) 0.0084(8) -0.0019(8) C13 0.0281(11) 0.0342(12) 0.0189(9) -0.0013(8) 0.0080(8) -0.0030(9) C14 0.0275(12) 0.0328(12) 0.0223(10) 0.0007(9) 0.0003(9) -0.0017(9) C15 0.0205(10) 0.0292(11) 0.0296(11) 0.0003(9) 0.0025(9) 0.0025(9) C16 0.0193(10) 0.0296(11) 0.0239(10) -0.0018(8) 0.0073(8) 0.0024(8) C21 0.0174(9) 0.0202(9) 0.0198(9) 0.0024(7) 0.0040(7) 0.0003(8) C22 0.0178(9) 0.0167(9) 0.0178(9) 0.0015(7) 0.0062(7) -0.0012(7) C23 0.0249(10) 0.0219(10) 0.0168(9) 0.0022(7) 0.0065(8) 0.0006(8) C24 0.0310(11) 0.0226(10) 0.0213(9) 0.0005(8) 0.0144(8) 0.0013(9) C25 0.0250(11) 0.0287(11) 0.0261(10) -0.0008(8) 0.0144(8) 0.0052(9) C26 0.0203(10) 0.0278(11) 0.0214(9) 0.0000(8) 0.0075(8) 0.0044(8) N6 0.0226(9) 0.0189(8) 0.0215(8) -0.0001(7) 0.0080(7) -0.0034(7) O7 0.0446(14) 0.0571(15) 0.109(2) -0.0257(15) -0.0351(14) 0.0038(11) O6 0.0507(14) 0.0841(18) 0.116(2) 0.0701(17) 0.0571(15) 0.0350(13) O8 0.0772(19) 0.134(3) 0.0482(14) -0.0188(16) 0.0287(13) 0.0061(18) O2 0.0233(8) 0.0245(8) 0.0278(7) -0.0019(6) 0.0128(6) -0.0032(6) _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 Co N1 2.0941(16) . ? Co N2 2.1121(17) . ? Co O2 2.1361(16) . ? Co N4 2.1376(16) . ? Co N3 2.1436(17) . ? Co O3 2.1525(15) . ? N1 C11 1.269(3) . ? N1 C1 1.478(3) . ? N2 C21 1.273(3) . ? N2 C3 1.485(2) . ? N3 C16 1.335(3) . ? N3 C12 1.353(3) . ? N4 C26 1.333(3) . ? N4 C22 1.353(2) . ? N5 O6 1.213(3) . ? N5 O8 1.215(3) . ? N5 O7 1.224(3) . ? O1 C5 1.433(3) . ? O1 H19 0.82(3) . ? O3 N6 1.286(2) . ? O4 N6 1.225(2) . ? O5 N6 1.242(2) . ? C1 C6 1.530(3) . ? C1 C2 1.533(3) . ? C1 H1A 1.0000 . ? C2 C3 1.535(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.534(3) . ? C3 H3 1.0000 . ? C4 C5 1.522(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.521(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C11 C12 1.465(3) . ? C11 H11 0.9500 . ? C12 C13 1.384(3) . ? C13 C14 1.389(3) . ? C13 H13 0.9500 . ? C14 C15 1.377(3) . ? C14 H14 0.9500 . ? C15 C16 1.390(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.470(3) . ? C21 H21 0.9500 . ? C22 C23 1.387(3) . ? C23 C24 1.390(3) . ? C23 H23 0.9500 . ? C24 C25 1.378(3) . ? C24 H24 0.9500 . ? C25 C26 1.393(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? O2 H2W 0.81(2) . ? O2 H1W 0.80(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Co N2 90.44(7) . . ? N1 Co O2 93.69(6) . . ? N2 Co O2 88.67(6) . . ? N1 Co N4 168.34(7) . . ? N2 Co N4 78.14(6) . . ? O2 Co N4 83.77(6) . . ? N1 Co N3 77.89(7) . . ? N2 Co N3 167.77(7) . . ? O2 Co N3 88.44(7) . . ? N4 Co N3 113.33(6) . . ? N1 Co O3 100.94(6) . . ? N2 Co O3 99.68(6) . . ? O2 Co O3 163.02(6) . . ? N4 Co O3 83.53(6) . . ? N3 Co O3 86.28(6) . . ? C11 N1 C1 118.02(17) . . ? C11 N1 Co 115.02(14) . . ? C1 N1 Co 126.95(13) . . ? C21 N2 C3 118.12(17) . . ? C21 N2 Co 114.04(14) . . ? C3 N2 Co 126.79(12) . . ? C16 N3 C12 117.64(18) . . ? C16 N3 Co 130.16(14) . . ? C12 N3 Co 112.19(13) . . ? C26 N4 C22 117.68(17) . . ? C26 N4 Co 129.89(13) . . ? C22 N4 Co 112.34(13) . . ? O6 N5 O8 117.1(3) . . ? O6 N5 O7 127.6(3) . . ? O8 N5 O7 115.3(3) . . ? C5 O1 H19 110(2) . . ? N6 O3 Co 122.49(12) . . ? N1 C1 C6 110.42(18) . . ? N1 C1 C2 109.93(16) . . ? C6 C1 C2 111.17(17) . . ? N1 C1 H1A 108.4 . . ? C6 C1 H1A 108.4 . . ? C2 C1 H1A 108.4 . . ? C1 C2 C3 114.41(17) . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2B 108.7 . . ? C3 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? N2 C3 C4 110.53(16) . . ? N2 C3 C2 109.38(16) . . ? C4 C3 C2 111.38(17) . . ? N2 C3 H3 108.5 . . ? C4 C3 H3 108.5 . . ? C2 C3 H3 108.5 . . ? C5 C4 C3 112.57(17) . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? O1 C5 C6 105.92(16) . . ? O1 C5 C4 110.95(18) . . ? C6 C5 C4 110.58(18) . . ? O1 C5 H5 109.8 . . ? C6 C5 H5 109.8 . . ? C4 C5 H5 109.8 . . ? C5 C6 C1 113.26(17) . . ? C5 C6 H6A 108.9 . . ? C1 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C1 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? N1 C11 C12 119.21(18) . . ? N1 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? N3 C12 C13 122.8(2) . . ? N3 C12 C11 115.21(18) . . ? C13 C12 C11 121.87(19) . . ? C12 C13 C14 118.7(2) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C15 C14 C13 118.7(2) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? C14 C15 C16 119.2(2) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? N3 C16 C15 122.8(2) . . ? N3 C16 H16 118.6 . . ? C15 C16 H16 118.6 . . ? N2 C21 C22 119.23(18) . . ? N2 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? N4 C22 C23 123.10(19) . . ? N4 C22 C21 115.59(17) . . ? C23 C22 C21 121.30(18) . . ? C22 C23 C24 118.26(19) . . ? C22 C23 H23 120.9 . . ? C24 C23 H23 120.9 . . ? C25 C24 C23 119.14(18) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C24 C25 C26 118.9(2) . . ? C24 C25 H25 120.5 . . ? C26 C25 H25 120.5 . . ? N4 C26 C25 122.88(19) . . ? N4 C26 H26 118.6 . . ? C25 C26 H26 118.6 . . ? O4 N6 O5 121.20(18) . . ? O4 N6 O3 120.25(18) . . ? O5 N6 O3 118.55(17) . . ? Co O2 H2W 120(2) . . ? Co O2 H1W 126(2) . . ? H2W O2 H1W 100(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Co N1 C11 -179.49(16) . . . . ? O2 Co N1 C11 91.81(16) . . . . ? N4 Co N1 C11 168.8(3) . . . . ? N3 Co N1 C11 4.20(16) . . . . ? O3 Co N1 C11 -79.54(16) . . . . ? N2 Co N1 C1 2.12(17) . . . . ? O2 Co N1 C1 -86.58(16) . . . . ? N4 Co N1 C1 -9.6(4) . . . . ? N3 Co N1 C1 -174.19(17) . . . . ? O3 Co N1 C1 102.07(16) . . . . ? N1 Co N2 C21 -170.19(15) . . . . ? O2 Co N2 C21 -76.50(15) . . . . ? N4 Co N2 C21 7.41(15) . . . . ? N3 Co N2 C21 -152.9(3) . . . . ? O3 Co N2 C21 88.64(15) . . . . ? N1 Co N2 C3 -2.26(16) . . . . ? O2 Co N2 C3 91.43(16) . . . . ? N4 Co N2 C3 175.34(17) . . . . ? N3 Co N2 C3 15.0(4) . . . . ? O3 Co N2 C3 -103.43(16) . . . . ? N1 Co N3 C16 175.2(2) . . . . ? N2 Co N3 C16 157.5(3) . . . . ? O2 Co N3 C16 81.05(19) . . . . ? N4 Co N3 C16 -1.5(2) . . . . ? O3 Co N3 C16 -82.80(19) . . . . ? N1 Co N3 C12 -6.17(14) . . . . ? N2 Co N3 C12 -23.9(4) . . . . ? O2 Co N3 C12 -100.28(15) . . . . ? N4 Co N3 C12 177.18(14) . . . . ? O3 Co N3 C12 95.86(15) . . . . ? N1 Co N4 C26 -169.8(3) . . . . ? N2 Co N4 C26 178.2(2) . . . . ? O2 Co N4 C26 -91.85(19) . . . . ? N3 Co N4 C26 -6.3(2) . . . . ? O3 Co N4 C26 76.85(19) . . . . ? N1 Co N4 C22 6.5(4) . . . . ? N2 Co N4 C22 -5.49(13) . . . . ? O2 Co N4 C22 84.46(14) . . . . ? N3 Co N4 C22 170.06(13) . . . . ? O3 Co N4 C22 -106.83(14) . . . . ? N1 Co O3 N6 37.95(16) . . . . ? N2 Co O3 N6 130.29(15) . . . . ? O2 Co O3 N6 -111.1(2) . . . . ? N4 Co O3 N6 -152.95(15) . . . . ? N3 Co O3 N6 -38.95(15) . . . . ? C11 N1 C1 C6 88.9(2) . . . . ? Co N1 C1 C6 -92.75(19) . . . . ? C11 N1 C1 C2 -148.09(19) . . . . ? Co N1 C1 C2 30.3(2) . . . . ? N1 C1 C2 C3 -73.7(2) . . . . ? C6 C1 C2 C3 48.9(2) . . . . ? C21 N2 C3 C4 -99.4(2) . . . . ? Co N2 C3 C4 93.13(19) . . . . ? C21 N2 C3 C2 137.65(19) . . . . ? Co N2 C3 C2 -29.8(2) . . . . ? C1 C2 C3 N2 73.2(2) . . . . ? C1 C2 C3 C4 -49.3(2) . . . . ? N2 C3 C4 C5 -69.3(2) . . . . ? C2 C3 C4 C5 52.5(2) . . . . ? C3 C4 C5 O1 -173.04(17) . . . . ? C3 C4 C5 C6 -55.8(2) . . . . ? O1 C5 C6 C1 176.14(18) . . . . ? C4 C5 C6 C1 55.9(2) . . . . ? N1 C1 C6 C5 70.2(2) . . . . ? C2 C1 C6 C5 -52.1(2) . . . . ? C1 N1 C11 C12 176.90(18) . . . . ? Co N1 C11 C12 -1.6(3) . . . . ? C16 N3 C12 C13 2.8(3) . . . . ? Co N3 C12 C13 -176.10(18) . . . . ? C16 N3 C12 C11 -173.92(19) . . . . ? Co N3 C12 C11 7.2(2) . . . . ? N1 C11 C12 N3 -4.0(3) . . . . ? N1 C11 C12 C13 179.3(2) . . . . ? N3 C12 C13 C14 -2.7(3) . . . . ? C11 C12 C13 C14 173.7(2) . . . . ? C12 C13 C14 C15 -0.2(3) . . . . ? C13 C14 C15 C16 2.8(4) . . . . ? C12 N3 C16 C15 0.1(3) . . . . ? Co N3 C16 C15 178.66(17) . . . . ? C14 C15 C16 N3 -2.8(4) . . . . ? C3 N2 C21 C22 -177.26(17) . . . . ? Co N2 C21 C22 -8.2(2) . . . . ? C26 N4 C22 C23 0.6(3) . . . . ? Co N4 C22 C23 -176.18(16) . . . . ? C26 N4 C22 C21 -179.98(18) . . . . ? Co N4 C22 C21 3.2(2) . . . . ? N2 C21 C22 N4 3.4(3) . . . . ? N2 C21 C22 C23 -177.2(2) . . . . ? N4 C22 C23 C24 0.0(3) . . . . ? C21 C22 C23 C24 -179.37(19) . . . . ? C22 C23 C24 C25 -0.1(3) . . . . ? C23 C24 C25 C26 -0.4(3) . . . . ? C22 N4 C26 C25 -1.2(3) . . . . ? Co N4 C26 C25 174.97(17) . . . . ? C24 C25 C26 N4 1.1(4) . . . . ? Co O3 N6 O4 -51.4(2) . . . . ? Co O3 N6 O5 129.27(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H19 O8 0.82(3) 2.40(3) 3.001(4) 130(3) 1_655 O1 H19 O6 0.82(3) 2.30(3) 3.111(4) 169(3) 1_655 O2 H1W O8 0.80(2) 2.37(2) 3.089(4) 149(3) 1_545 O2 H1W O7 0.80(2) 2.17(2) 2.923(4) 156(3) 1_545 O2 H2W O5 0.81(2) 1.96(2) 2.740(2) 161(3) 1_545 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.924 _refine_diff_density_min -0.993 _refine_diff_density_rms 0.065 # === END data_compound2 _database_code_depnum_ccdc_archive 'CCDC 828953' #TrackingRef '- CoCu-allstructures-rev.cif' _publ_section_exptl_refinement ; The structure was solved by direct methods. All non-H atoms were refined anisotropically. H atoms were included in calculated positions, except those bonded to O1 and O2, which were found by difference Fourier techniques and refined isotropically, with restraints on the bond lengths. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 Cu N5 O5, N O3 ' _chemical_formula_sum 'C18 H22 Cu N6 O8' _chemical_formula_weight 513.97 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.0362(3) _cell_length_b 7.3893(2) _cell_length_c 29.2108(6) _cell_angle_alpha 90.00 _cell_angle_beta 109.246(2) _cell_angle_gamma 90.00 _cell_volume 2045.22(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4625 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1060 _exptl_absorpt_coefficient_mu 1.130 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19463 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.46 _reflns_number_total 4622 _reflns_number_gt 3785 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material 'SHELXTL (Bruker, 2001)' _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^)+(0.0398P)^2^+0.8384P] 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 4622 _refine_ls_number_parameters 310 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0813 _refine_ls_wR_factor_gt 0.0766 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.89738(2) 0.20578(3) 0.875138(8) 0.01991(8) Uani 1 1 d . . . O1 O 1.36123(16) 0.4311(2) 0.86106(6) 0.0313(3) Uani 1 1 d D . . O2 O 0.80946(16) -0.0745(2) 0.89187(6) 0.0280(3) Uani 1 1 d D . . O3 O 0.93200(16) 0.5385(2) 0.86489(5) 0.0289(3) Uani 1 1 d . . . O4 O 0.95859(18) 0.5346(2) 0.79410(6) 0.0381(4) Uani 1 1 d . . . O5 O 0.83195(18) 0.7429(2) 0.81126(6) 0.0362(4) Uani 1 1 d . . . N1 N 0.97117(16) 0.1212(2) 0.82325(5) 0.0192(3) Uani 1 1 d . . . N2 N 1.08222(16) 0.1518(2) 0.92733(5) 0.0190(3) Uani 1 1 d . . . N3 N 0.71752(17) 0.2404(2) 0.81598(5) 0.0198(3) Uani 1 1 d . . . N4 N 0.84872(16) 0.3014(2) 0.93380(5) 0.0192(3) Uani 1 1 d . . . N6 N 0.90771(17) 0.6049(2) 0.82305(6) 0.0221(3) Uani 1 1 d . . . C1 C 1.11057(19) 0.0389(3) 0.82957(7) 0.0208(4) Uani 1 1 d . . . H1 H 1.0987 -0.0511 0.8029 0.025 Uiso 1 1 calc R . . C2 C 1.1635(2) -0.0618(3) 0.87780(7) 0.0217(4) Uani 1 1 d . . . H2A H 1.2444 -0.1392 0.8782 0.026 Uiso 1 1 calc R . . H2B H 1.0876 -0.1418 0.8807 0.026 Uiso 1 1 calc R . . C3 C 1.20955(19) 0.0661(3) 0.92145(7) 0.0206(4) Uani 1 1 d . . . H3 H 1.2578 -0.0066 0.9512 0.025 Uiso 1 1 calc R . . C4 C 1.3126(2) 0.2110(3) 0.91579(7) 0.0230(4) Uani 1 1 d . . . H4A H 1.3321 0.2977 0.9430 0.028 Uiso 1 1 calc R . . H4B H 1.4029 0.1523 0.9176 0.028 Uiso 1 1 calc R . . C5 C 1.2560(2) 0.3141(3) 0.86814(7) 0.0227(4) Uani 1 1 d . . . H5 H 1.1716 0.3867 0.8678 0.027 Uiso 1 1 calc R . . C6 C 1.2154(2) 0.1826(3) 0.82550(7) 0.0238(4) Uani 1 1 d . . . H6A H 1.3016 0.1222 0.8238 0.029 Uiso 1 1 calc R . . H6B H 1.1734 0.2514 0.7951 0.029 Uiso 1 1 calc R . . C7 C 0.8862(2) 0.1433(3) 0.78058(7) 0.0231(4) Uani 1 1 d . . . H7 H 0.9139 0.1158 0.7533 0.028 Uiso 1 1 calc R . . C8 C 0.7447(2) 0.2119(3) 0.77425(7) 0.0205(4) Uani 1 1 d . . . C9 C 0.6449(2) 0.2343(3) 0.72899(7) 0.0274(5) Uani 1 1 d . . . H9 H 0.6689 0.2171 0.7004 0.033 Uiso 1 1 calc R . . C10 C 0.5083(2) 0.2826(3) 0.72618(7) 0.0284(5) Uani 1 1 d . . . H10 H 0.4373 0.3001 0.6956 0.034 Uiso 1 1 calc R . . C11 C 0.4781(2) 0.3044(3) 0.76835(7) 0.0262(4) Uani 1 1 d . . . H11 H 0.3850 0.3337 0.7674 0.031 Uiso 1 1 calc R . . C12 C 0.5850(2) 0.2831(3) 0.81247(7) 0.0253(4) Uani 1 1 d . . . H12 H 0.5632 0.2997 0.8415 0.030 Uiso 1 1 calc R . . C13 C 1.0779(2) 0.1760(3) 0.96996(7) 0.0203(4) Uani 1 1 d . . . H13 H 1.1549 0.1408 0.9975 0.024 Uiso 1 1 calc R . . C14 C 0.9520(2) 0.2591(3) 0.97584(6) 0.0188(4) Uani 1 1 d . . . C15 C 0.9412(2) 0.2941(3) 1.02091(7) 0.0218(4) Uani 1 1 d . . . H15 H 1.0159 0.2634 1.0496 0.026 Uiso 1 1 calc R . . C16 C 0.8191(2) 0.3749(3) 1.02342(7) 0.0250(4) Uani 1 1 d . . . H16 H 0.8079 0.3979 1.0539 0.030 Uiso 1 1 calc R . . C17 C 0.7142(2) 0.4213(3) 0.98104(7) 0.0270(4) Uani 1 1 d . . . H17 H 0.6301 0.4780 0.9819 0.032 Uiso 1 1 calc R . . C18 C 0.7336(2) 0.3838(3) 0.93711(7) 0.0261(4) Uani 1 1 d . . . H18 H 0.6618 0.4184 0.9080 0.031 Uiso 1 1 calc R . . O6 O 0.44631(17) 0.6917(2) 0.93837(6) 0.0393(4) Uani 1 1 d . . . O7 O 0.61139(19) 0.8946(3) 0.95962(7) 0.0544(5) Uani 1 1 d . . . O8 O 0.5255(2) 0.8121(3) 0.88563(6) 0.0544(5) Uani 1 1 d . . . N5 N 0.52927(18) 0.7997(3) 0.92815(6) 0.0274(4) Uani 1 1 d . . . H1W H 0.7349(19) -0.082(4) 0.8971(9) 0.045(8) Uiso 1 1 d D . . H19 H 1.381(3) 0.510(3) 0.8816(8) 0.041(8) Uiso 1 1 d D . . H2W H 0.808(3) -0.140(3) 0.8700(8) 0.043(8) Uiso 1 1 d 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 Cu1 0.01658(12) 0.02945(14) 0.01337(13) 0.00007(9) 0.00446(9) 0.00474(10) O1 0.0330(8) 0.0306(9) 0.0365(9) -0.0043(7) 0.0196(7) -0.0077(7) O2 0.0259(8) 0.0282(8) 0.0306(9) -0.0009(6) 0.0102(7) 0.0002(6) O3 0.0397(8) 0.0282(8) 0.0196(7) 0.0034(6) 0.0107(6) 0.0001(7) O4 0.0535(10) 0.0372(10) 0.0341(9) 0.0049(7) 0.0287(8) 0.0080(8) O5 0.0411(10) 0.0321(9) 0.0291(8) 0.0030(6) 0.0031(7) 0.0133(7) N1 0.0183(8) 0.0209(8) 0.0189(8) 0.0012(6) 0.0068(6) 0.0018(7) N2 0.0172(8) 0.0218(8) 0.0174(8) 0.0014(6) 0.0047(6) 0.0004(6) N3 0.0183(8) 0.0251(9) 0.0155(8) -0.0005(6) 0.0046(6) 0.0014(6) N4 0.0185(8) 0.0225(9) 0.0158(8) 0.0010(6) 0.0048(6) 0.0018(7) N6 0.0214(8) 0.0227(9) 0.0221(9) -0.0007(6) 0.0068(7) -0.0040(7) C1 0.0189(9) 0.0232(10) 0.0209(10) -0.0028(7) 0.0074(7) 0.0035(8) C2 0.0201(9) 0.0208(10) 0.0236(10) 0.0001(7) 0.0064(8) 0.0022(8) C3 0.0177(9) 0.0233(10) 0.0207(10) 0.0016(7) 0.0061(7) 0.0032(7) C4 0.0184(9) 0.0259(10) 0.0247(10) -0.0025(8) 0.0072(8) 0.0012(8) C5 0.0199(9) 0.0227(10) 0.0275(10) -0.0001(8) 0.0106(8) -0.0020(8) C6 0.0200(9) 0.0299(11) 0.0235(10) 0.0005(8) 0.0101(8) 0.0016(8) C7 0.0260(10) 0.0280(11) 0.0172(10) 0.0009(7) 0.0098(8) 0.0020(8) C8 0.0211(9) 0.0245(10) 0.0159(9) 0.0005(7) 0.0060(7) 0.0009(8) C9 0.0267(11) 0.0387(13) 0.0163(10) 0.0015(8) 0.0063(8) 0.0020(9) C10 0.0233(10) 0.0376(13) 0.0201(10) 0.0025(8) 0.0013(8) 0.0013(9) C11 0.0187(9) 0.0331(12) 0.0246(10) 0.0004(8) 0.0041(8) 0.0033(9) C12 0.0204(10) 0.0362(12) 0.0200(10) -0.0018(8) 0.0075(8) 0.0013(9) C13 0.0180(9) 0.0240(11) 0.0165(9) 0.0023(7) 0.0024(7) 0.0003(7) C14 0.0201(9) 0.0192(10) 0.0171(9) 0.0025(7) 0.0060(7) -0.0005(7) C15 0.0233(10) 0.0239(10) 0.0170(9) 0.0033(7) 0.0050(7) 0.0003(8) C16 0.0319(11) 0.0268(11) 0.0191(10) 0.0007(8) 0.0123(8) 0.0013(9) C17 0.0256(10) 0.0326(12) 0.0243(10) -0.0017(8) 0.0102(8) 0.0056(9) C18 0.0229(10) 0.0339(12) 0.0201(10) 0.0007(8) 0.0054(8) 0.0079(9) O6 0.0320(9) 0.0451(11) 0.0445(10) 0.0141(8) 0.0175(7) 0.0063(8) O7 0.0363(10) 0.0600(13) 0.0504(11) -0.0176(9) -0.0080(8) -0.0013(9) O8 0.0497(11) 0.0896(17) 0.0267(9) -0.0056(9) 0.0166(8) -0.0160(11) N5 0.0189(8) 0.0336(10) 0.0266(10) 0.0006(7) 0.0032(7) 0.0042(8) _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 N1 1.9940(15) . ? Cu1 N2 2.0151(15) . ? Cu1 N4 2.0555(15) . ? Cu1 N3 2.0623(16) . ? Cu1 O2 2.3644(16) . ? Cu1 O3 2.5150(15) . ? O1 C5 1.432(2) . ? O1 H19 0.811(17) . ? O2 H1W 0.814(14) . ? O2 H2W 0.797(14) . ? O3 N6 1.264(2) . ? O4 N6 1.237(2) . ? O5 N6 1.250(2) . ? N1 C7 1.268(2) . ? N1 C1 1.480(2) . ? N2 C13 1.273(2) . ? N2 C3 1.486(2) . ? N3 C12 1.337(2) . ? N3 C8 1.351(2) . ? N4 C18 1.337(2) . ? N4 C14 1.357(2) . ? C1 C2 1.526(3) . ? C1 C6 1.527(3) . ? C1 H1 1.0000 . ? C2 C3 1.531(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.535(3) . ? C3 H3 1.0000 . ? C4 C5 1.523(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.525(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.461(3) . ? C7 H7 0.9500 . ? C8 C9 1.380(3) . ? C9 C10 1.393(3) . ? C9 H9 0.9500 . ? C10 C11 1.372(3) . ? C10 H10 0.9500 . ? C11 C12 1.388(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.465(3) . ? C13 H13 0.9500 . ? C14 C15 1.380(3) . ? C15 C16 1.387(3) . ? C15 H15 0.9500 . ? C16 C17 1.378(3) . ? C16 H16 0.9500 . ? C17 C18 1.388(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? O6 N5 1.258(2) . ? O7 N5 1.231(2) . ? O8 N5 1.233(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 91.89(6) . . ? N1 Cu1 N4 172.36(6) . . ? N2 Cu1 N4 81.36(6) . . ? N1 Cu1 N3 81.01(6) . . ? N2 Cu1 N3 172.61(6) . . ? N4 Cu1 N3 105.85(6) . . ? N1 Cu1 O2 98.05(6) . . ? N2 Cu1 O2 89.05(6) . . ? N4 Cu1 O2 85.48(6) . . ? N3 Cu1 O2 89.92(6) . . ? N1 Cu1 O3 96.63(6) . . ? N2 Cu1 O3 98.91(6) . . ? N4 Cu1 O3 80.99(6) . . ? N3 Cu1 O3 84.04(6) . . ? O2 Cu1 O3 163.05(5) . . ? C5 O1 H19 109.5(19) . . ? Cu1 O2 H1W 122(2) . . ? Cu1 O2 H2W 106(2) . . ? H1W O2 H2W 110(3) . . ? N6 O3 Cu1 120.28(12) . . ? C7 N1 C1 118.53(15) . . ? C7 N1 Cu1 114.13(13) . . ? C1 N1 Cu1 127.35(12) . . ? C13 N2 C3 118.76(16) . . ? C13 N2 Cu1 113.10(13) . . ? C3 N2 Cu1 127.54(12) . . ? C12 N3 C8 117.32(16) . . ? C12 N3 Cu1 131.84(13) . . ? C8 N3 Cu1 110.84(12) . . ? C18 N4 C14 117.35(16) . . ? C18 N4 Cu1 131.69(13) . . ? C14 N4 Cu1 110.80(12) . . ? O4 N6 O5 120.29(16) . . ? O4 N6 O3 120.45(17) . . ? O5 N6 O3 119.26(16) . . ? N1 C1 C2 110.04(15) . . ? N1 C1 C6 110.57(16) . . ? C2 C1 C6 111.84(16) . . ? N1 C1 H1 108.1 . . ? C2 C1 H1 108.1 . . ? C6 C1 H1 108.1 . . ? C1 C2 C3 112.67(17) . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? N2 C3 C2 108.93(15) . . ? N2 C3 C4 110.57(16) . . ? C2 C3 C4 111.71(15) . . ? N2 C3 H3 108.5 . . ? C2 C3 H3 108.5 . . ? C4 C3 H3 108.5 . . ? C5 C4 C3 112.68(16) . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? O1 C5 C4 111.30(16) . . ? O1 C5 C6 106.13(15) . . ? C4 C5 C6 110.28(17) . . ? O1 C5 H5 109.7 . . ? C4 C5 H5 109.7 . . ? C6 C5 H5 109.7 . . ? C5 C6 C1 112.63(15) . . ? C5 C6 H6A 109.1 . . ? C1 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C1 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? N1 C7 C8 118.70(17) . . ? N1 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? N3 C8 C9 123.21(18) . . ? N3 C8 C7 114.62(16) . . ? C9 C8 C7 122.05(17) . . ? C8 C9 C10 118.44(19) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? C11 C10 C9 118.80(18) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C10 C11 C12 119.25(19) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? N3 C12 C11 122.89(18) . . ? N3 C12 H12 118.6 . . ? C11 C12 H12 118.6 . . ? N2 C13 C14 118.86(17) . . ? N2 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? N4 C14 C15 122.95(17) . . ? N4 C14 C13 114.92(16) . . ? C15 C14 C13 122.12(17) . . ? C14 C15 C16 118.63(17) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C17 C16 C15 119.11(18) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 118.85(19) . . ? C16 C17 H17 120.6 . . ? C18 C17 H17 120.6 . . ? N4 C18 C17 123.06(18) . . ? N4 C18 H18 118.5 . . ? C17 C18 H18 118.5 . . ? O7 N5 O8 120.0(2) . . ? O7 N5 O6 121.10(19) . . ? O8 N5 O6 118.87(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 O3 N6 38.63(14) . . . . ? N2 Cu1 O3 N6 131.60(13) . . . . ? N4 Cu1 O3 N6 -148.70(14) . . . . ? N3 Cu1 O3 N6 -41.57(14) . . . . ? O2 Cu1 O3 N6 -111.25(19) . . . . ? N2 Cu1 N1 C7 -175.43(15) . . . . ? N4 Cu1 N1 C7 -147.6(5) . . . . ? N3 Cu1 N1 C7 6.63(15) . . . . ? O2 Cu1 N1 C7 95.26(15) . . . . ? O3 Cu1 N1 C7 -76.24(15) . . . . ? N2 Cu1 N1 C1 4.33(16) . . . . ? N4 Cu1 N1 C1 32.2(6) . . . . ? N3 Cu1 N1 C1 -173.61(16) . . . . ? O2 Cu1 N1 C1 -84.98(15) . . . . ? O3 Cu1 N1 C1 103.52(15) . . . . ? N1 Cu1 N2 C13 -174.96(14) . . . . ? N4 Cu1 N2 C13 8.64(14) . . . . ? N3 Cu1 N2 C13 -158.9(5) . . . . ? O2 Cu1 N2 C13 -76.94(14) . . . . ? O3 Cu1 N2 C13 88.03(14) . . . . ? N1 Cu1 N2 C3 -4.05(16) . . . . ? N4 Cu1 N2 C3 179.55(16) . . . . ? N3 Cu1 N2 C3 12.0(6) . . . . ? O2 Cu1 N2 C3 93.97(16) . . . . ? O3 Cu1 N2 C3 -101.07(15) . . . . ? N1 Cu1 N3 C12 172.1(2) . . . . ? N2 Cu1 N3 C12 155.9(4) . . . . ? N4 Cu1 N3 C12 -11.3(2) . . . . ? O2 Cu1 N3 C12 74.0(2) . . . . ? O3 Cu1 N3 C12 -90.1(2) . . . . ? N1 Cu1 N3 C8 -7.42(13) . . . . ? N2 Cu1 N3 C8 -23.7(6) . . . . ? N4 Cu1 N3 C8 169.13(13) . . . . ? O2 Cu1 N3 C8 -105.59(14) . . . . ? O3 Cu1 N3 C8 90.28(13) . . . . ? N1 Cu1 N4 C18 148.5(4) . . . . ? N2 Cu1 N4 C18 176.7(2) . . . . ? N3 Cu1 N4 C18 -4.9(2) . . . . ? O2 Cu1 N4 C18 -93.58(19) . . . . ? O3 Cu1 N4 C18 76.18(19) . . . . ? N1 Cu1 N4 C14 -36.2(6) . . . . ? N2 Cu1 N4 C14 -8.04(13) . . . . ? N3 Cu1 N4 C14 170.30(13) . . . . ? O2 Cu1 N4 C14 81.68(13) . . . . ? O3 Cu1 N4 C14 -108.57(13) . . . . ? Cu1 O3 N6 O4 -49.8(2) . . . . ? Cu1 O3 N6 O5 130.39(16) . . . . ? C7 N1 C1 C2 -151.29(18) . . . . ? Cu1 N1 C1 C2 29.0(2) . . . . ? C7 N1 C1 C6 84.7(2) . . . . ? Cu1 N1 C1 C6 -95.08(17) . . . . ? N1 C1 C2 C3 -71.9(2) . . . . ? C6 C1 C2 C3 51.4(2) . . . . ? C13 N2 C3 C2 141.30(18) . . . . ? Cu1 N2 C3 C2 -29.2(2) . . . . ? C13 N2 C3 C4 -95.6(2) . . . . ? Cu1 N2 C3 C4 93.96(18) . . . . ? C1 C2 C3 N2 71.5(2) . . . . ? C1 C2 C3 C4 -50.9(2) . . . . ? N2 C3 C4 C5 -68.3(2) . . . . ? C2 C3 C4 C5 53.2(2) . . . . ? C3 C4 C5 O1 -172.41(15) . . . . ? C3 C4 C5 C6 -54.9(2) . . . . ? O1 C5 C6 C1 175.92(16) . . . . ? C4 C5 C6 C1 55.3(2) . . . . ? N1 C1 C6 C5 69.1(2) . . . . ? C2 C1 C6 C5 -53.9(2) . . . . ? C1 N1 C7 C8 175.50(17) . . . . ? Cu1 N1 C7 C8 -4.7(2) . . . . ? C12 N3 C8 C9 3.5(3) . . . . ? Cu1 N3 C8 C9 -176.86(17) . . . . ? C12 N3 C8 C7 -172.51(19) . . . . ? Cu1 N3 C8 C7 7.1(2) . . . . ? N1 C7 C8 N3 -1.9(3) . . . . ? N1 C7 C8 C9 -178.0(2) . . . . ? N3 C8 C9 C10 -2.2(3) . . . . ? C7 C8 C9 C10 173.5(2) . . . . ? C8 C9 C10 C11 -0.6(3) . . . . ? C9 C10 C11 C12 1.9(3) . . . . ? C8 N3 C12 C11 -2.1(3) . . . . ? Cu1 N3 C12 C11 178.40(16) . . . . ? C10 C11 C12 N3 -0.6(4) . . . . ? C3 N2 C13 C14 -179.53(17) . . . . ? Cu1 N2 C13 C14 -7.8(2) . . . . ? C18 N4 C14 C15 1.4(3) . . . . ? Cu1 N4 C14 C15 -174.59(15) . . . . ? C18 N4 C14 C13 -177.54(18) . . . . ? Cu1 N4 C14 C13 6.5(2) . . . . ? N2 C13 C14 N4 0.7(3) . . . . ? N2 C13 C14 C15 -178.24(18) . . . . ? N4 C14 C15 C16 0.4(3) . . . . ? C13 C14 C15 C16 179.31(19) . . . . ? C14 C15 C16 C17 -1.5(3) . . . . ? C15 C16 C17 C18 0.7(3) . . . . ? C14 N4 C18 C17 -2.3(3) . . . . ? Cu1 N4 C18 C17 172.72(16) . . . . ? C16 C17 C18 N4 1.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H19 O8 0.811(17) 2.65(2) 3.221(3) 129(2) 1_655 O1 H19 O6 0.811(17) 2.067(17) 2.875(2) 174(3) 1_655 O2 H2W O5 0.797(14) 2.005(15) 2.787(2) 167(3) 1_545 O2 H1W O7 0.814(14) 2.528(18) 3.242(3) 147(2) 1_545 O2 H1W O8 0.814(14) 2.162(18) 2.918(2) 155(3) 1_545 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.401 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.060 # === END data_compound3 _database_code_depnum_ccdc_archive 'CCDC 828954' #TrackingRef '- CoCu-allstructures-rev.cif' _publ_section_exptl_refinement ; The structure was solved by direct methods. All non-H atoms were refined anisotropically. H atoms were included in calculated positions, except those bonded to O1 and O2, which were found by difference Fourier techniques and refined isotropically, with restraints on the bond lengths. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 N5 O5 Zn, N O3' _chemical_formula_sum 'C18 H22 N6 O8 Zn' _chemical_formula_weight 515.81 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 9.9335(3) _cell_length_b 7.3304(2) _cell_length_c 29.8838(9) _cell_angle_alpha 90.00 _cell_angle_beta 108.133(2) _cell_angle_gamma 90.00 _cell_volume 2067.96(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 36199 _cell_measurement_theta_min 1.62 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.657 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 1.249 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.823 _exptl_absorpt_correction_T_max 0.882 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ? _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 15290 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4654 _reflns_number_gt 3837 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0320P)^2^+3.3960P] 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 4654 _refine_ls_number_parameters 310 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 Zn Zn 0.89053(3) 0.20975(4) 0.874683(9) 0.02102(9) Uani 1 1 d . . . O1 O 1.3691(2) 0.4316(3) 0.86167(8) 0.0339(5) Uani 1 1 d . . . O2 O 0.8131(2) -0.0550(3) 0.88832(7) 0.0276(4) Uani 1 1 d D . . O3 O 0.9224(2) 0.5144(3) 0.86647(6) 0.0276(4) Uani 1 1 d . . . O4 O 0.9621(3) 0.5222(3) 0.79903(8) 0.0448(6) Uani 1 1 d . . . O5 O 0.8323(2) 0.7288(3) 0.81589(7) 0.0371(5) Uani 1 1 d . . . N1 N 0.9793(2) 0.1125(3) 0.82361(7) 0.0220(4) Uani 1 1 d . . . N2 N 1.0875(2) 0.1549(3) 0.92757(7) 0.0214(4) Uani 1 1 d . . . N3 N 0.7153(2) 0.2367(3) 0.81180(7) 0.0216(5) Uani 1 1 d . . . N4 N 0.8459(2) 0.2969(3) 0.93645(7) 0.0190(4) Uani 1 1 d . . . N5 N 0.9061(2) 0.5888(3) 0.82660(7) 0.0237(5) Uani 1 1 d . . . C1 C 1.1213(3) 0.0322(4) 0.83144(9) 0.0245(5) Uani 1 1 d . . . H1 H 1.1143 -0.0608 0.8063 0.029 Uiso 1 1 calc R . . C2 C 1.1705(3) -0.0645(4) 0.87929(9) 0.0247(5) Uani 1 1 d . . . H2A H 1.2517 -0.1445 0.8802 0.030 Uiso 1 1 calc R . . H2B H 1.0928 -0.1432 0.8822 0.030 Uiso 1 1 calc R . . C3 C 1.2151(3) 0.0657(4) 0.92163(9) 0.0229(5) Uani 1 1 d . . . H3 H 1.2625 -0.0068 0.9506 0.027 Uiso 1 1 calc R . . C4 C 1.3188(3) 0.2104(4) 0.91536(9) 0.0246(5) Uani 1 1 d . . . H4A H 1.3378 0.2991 0.9416 0.030 Uiso 1 1 calc R . . H4B H 1.4097 0.1509 0.9169 0.030 Uiso 1 1 calc R . . C5 C 1.2629(3) 0.3120(4) 0.86886(9) 0.0252(6) Uani 1 1 d . . . H5 H 1.1769 0.3838 0.8683 0.030 Uiso 1 1 calc R . . C6 C 1.2266(3) 0.1780(4) 0.82767(10) 0.0276(6) Uani 1 1 d . . . H6A H 1.1863 0.2464 0.7979 0.033 Uiso 1 1 calc R . . H6B H 1.3146 0.1181 0.8264 0.033 Uiso 1 1 calc R . . C7 C 0.8964(3) 0.1235(4) 0.78184(9) 0.0261(6) Uani 1 1 d . . . H7 H 0.9275 0.0861 0.7562 0.031 Uiso 1 1 calc R . . C8 C 0.7523(3) 0.1940(4) 0.77303(9) 0.0229(5) Uani 1 1 d . . . C9 C 0.6583(3) 0.2064(4) 0.72789(9) 0.0292(6) Uani 1 1 d . . . H9 H 0.6883 0.1801 0.7013 0.035 Uiso 1 1 calc R . . C10 C 0.5192(3) 0.2579(4) 0.72206(10) 0.0313(6) Uani 1 1 d . . . H10 H 0.4525 0.2675 0.6915 0.038 Uiso 1 1 calc R . . C11 C 0.4799(3) 0.2946(4) 0.76138(9) 0.0285(6) Uani 1 1 d . . . H11 H 0.3846 0.3256 0.7584 0.034 Uiso 1 1 calc R . . C12 C 0.5813(3) 0.2857(4) 0.80552(9) 0.0265(5) Uani 1 1 d . . . H12 H 0.5541 0.3158 0.8324 0.032 Uiso 1 1 calc R . . C13 C 1.0808(3) 0.1772(3) 0.96897(9) 0.0218(5) Uani 1 1 d . . . H13 H 1.1580 0.1412 0.9954 0.026 Uiso 1 1 calc R . . C14 C 0.9537(3) 0.2586(3) 0.97609(8) 0.0197(5) Uani 1 1 d . . . C15 C 0.9455(3) 0.2934(4) 1.02075(8) 0.0226(5) Uani 1 1 d . . . H15 H 1.0227 0.2654 1.0480 0.027 Uiso 1 1 calc R . . C16 C 0.8223(3) 0.3697(4) 1.02486(9) 0.0262(6) Uani 1 1 d . . . H16 H 0.8139 0.3952 1.0550 0.031 Uiso 1 1 calc R . . C17 C 0.7120(3) 0.4085(4) 0.98476(9) 0.0283(6) Uani 1 1 d . . . H17 H 0.6264 0.4600 0.9869 0.034 Uiso 1 1 calc R . . C18 C 0.7285(3) 0.3709(4) 0.94121(9) 0.0250(5) Uani 1 1 d . . . H18 H 0.6528 0.3991 0.9136 0.030 Uiso 1 1 calc R . . O6 O 0.4573(3) 0.6923(4) 0.93916(10) 0.0551(7) Uani 1 1 d . . . O7 O 0.6199(3) 0.9004(4) 0.95712(12) 0.0900(12) Uani 1 1 d . . . O8 O 0.5373(3) 0.8076(5) 0.88747(10) 0.0749(9) Uani 1 1 d . . . N6 N 0.5401(2) 0.8001(4) 0.92879(8) 0.0315(5) Uani 1 1 d . . . H2W H 0.813(4) -0.132(4) 0.8692(11) 0.045(11) Uiso 1 1 d D . . H1W H 0.738(3) -0.064(5) 0.8944(13) 0.054(11) Uiso 1 1 d D . . H19 H 1.387(4) 0.520(6) 0.8819(15) 0.070(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn 0.01898(15) 0.03007(17) 0.01504(14) -0.00004(12) 0.00679(10) 0.00423(13) O1 0.0341(11) 0.0327(12) 0.0422(12) -0.0002(10) 0.0222(9) -0.0076(9) O2 0.0265(10) 0.0290(11) 0.0291(10) -0.0009(9) 0.0114(8) -0.0005(9) O3 0.0374(10) 0.0269(10) 0.0199(9) 0.0028(7) 0.0109(8) -0.0010(8) O4 0.0640(15) 0.0458(14) 0.0393(12) 0.0084(10) 0.0374(11) 0.0139(12) O5 0.0470(12) 0.0317(12) 0.0286(10) 0.0025(9) 0.0062(9) 0.0144(10) N1 0.0214(10) 0.0228(12) 0.0237(11) -0.0002(9) 0.0100(8) 0.0013(9) N2 0.0175(10) 0.0256(12) 0.0217(10) 0.0020(8) 0.0071(8) 0.0013(9) N3 0.0213(10) 0.0280(12) 0.0165(9) -0.0013(8) 0.0074(8) 0.0024(9) N4 0.0200(10) 0.0222(11) 0.0156(9) 0.0014(8) 0.0068(7) 0.0011(9) N5 0.0262(11) 0.0250(12) 0.0210(10) 0.0008(9) 0.0090(9) -0.0026(9) C1 0.0235(12) 0.0277(14) 0.0254(13) -0.0046(11) 0.0122(10) 0.0025(11) C2 0.0227(12) 0.0220(14) 0.0304(13) 0.0013(11) 0.0097(10) 0.0047(11) C3 0.0195(12) 0.0250(14) 0.0248(12) 0.0024(10) 0.0078(10) 0.0026(10) C4 0.0194(12) 0.0266(14) 0.0287(13) -0.0016(11) 0.0087(10) 0.0005(11) C5 0.0225(12) 0.0260(15) 0.0317(13) 0.0023(11) 0.0151(10) -0.0007(11) C6 0.0244(13) 0.0350(17) 0.0277(13) 0.0011(11) 0.0141(11) 0.0009(11) C7 0.0277(13) 0.0341(16) 0.0202(12) -0.0027(11) 0.0131(10) 0.0002(12) C8 0.0247(12) 0.0265(14) 0.0184(11) -0.0006(10) 0.0080(9) -0.0008(11) C9 0.0313(14) 0.0396(16) 0.0174(12) 0.0011(12) 0.0086(10) -0.0012(13) C10 0.0318(14) 0.0352(17) 0.0222(13) 0.0033(11) 0.0015(11) -0.0006(12) C11 0.0223(13) 0.0332(15) 0.0269(13) 0.0011(12) 0.0031(10) 0.0037(12) C12 0.0239(12) 0.0315(15) 0.0250(13) -0.0024(12) 0.0088(10) 0.0009(12) C13 0.0204(12) 0.0238(14) 0.0199(12) 0.0030(10) 0.0045(9) 0.0012(10) C14 0.0217(12) 0.0200(13) 0.0178(11) 0.0020(9) 0.0067(9) -0.0011(10) C15 0.0290(13) 0.0224(13) 0.0158(11) 0.0014(10) 0.0060(9) -0.0010(11) C16 0.0343(14) 0.0277(14) 0.0201(12) -0.0006(11) 0.0134(11) 0.0010(12) C17 0.0272(13) 0.0363(16) 0.0251(13) 0.0005(11) 0.0136(11) 0.0057(12) C18 0.0222(12) 0.0337(15) 0.0200(12) 0.0011(11) 0.0079(10) 0.0050(11) O6 0.0447(13) 0.0624(17) 0.0689(17) 0.0306(14) 0.0329(12) 0.0144(12) O7 0.0514(17) 0.067(2) 0.108(3) -0.0355(19) -0.0383(17) 0.0067(15) O8 0.0715(19) 0.122(3) 0.0410(15) -0.0041(16) 0.0315(14) -0.0059(19) N6 0.0236(11) 0.0370(14) 0.0322(13) 0.0025(11) 0.0060(9) 0.0046(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 Zn N1 2.110(2) . ? Zn N4 2.1262(19) . ? Zn N2 2.136(2) . ? Zn N3 2.137(2) . ? Zn O2 2.173(2) . ? Zn O3 2.280(2) . ? O1 C5 1.438(3) . ? O1 H19 0.87(4) . ? O2 H2W 0.80(3) . ? O2 H1W 0.83(3) . ? O3 N5 1.274(3) . ? O4 N5 1.230(3) . ? O5 N5 1.243(3) . ? N1 C7 1.266(3) . ? N1 C1 1.479(3) . ? N2 C13 1.270(3) . ? N2 C3 1.485(3) . ? N3 C12 1.334(3) . ? N3 C8 1.357(3) . ? N4 C18 1.333(3) . ? N4 C14 1.356(3) . ? C1 C6 1.524(4) . ? C1 C2 1.533(4) . ? C1 H1 1.0000 . ? C2 C3 1.536(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.531(4) . ? C3 H3 1.0000 . ? C4 C5 1.521(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.527(4) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.467(4) . ? C7 H7 0.9500 . ? C8 C9 1.384(3) . ? C9 C10 1.390(4) . ? C9 H9 0.9500 . ? C10 C11 1.375(4) . ? C10 H10 0.9500 . ? C11 C12 1.390(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.471(3) . ? C13 H13 0.9500 . ? C14 C15 1.386(3) . ? C15 C16 1.386(4) . ? C15 H15 0.9500 . ? C16 C17 1.378(4) . ? C16 H16 0.9500 . ? C17 C18 1.389(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? O6 N6 1.247(3) . ? O7 N6 1.212(3) . ? O8 N6 1.228(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn N4 167.52(8) . . ? N1 Zn N2 88.79(8) . . ? N4 Zn N2 78.74(8) . . ? N1 Zn N3 78.72(8) . . ? N4 Zn N3 113.75(8) . . ? N2 Zn N3 167.46(8) . . ? N1 Zn O2 94.93(8) . . ? N4 Zn O2 85.64(8) . . ? N2 Zn O2 89.39(8) . . ? N3 Zn O2 90.49(8) . . ? N1 Zn O3 98.62(8) . . ? N4 Zn O3 82.67(7) . . ? N2 Zn O3 97.94(8) . . ? N3 Zn O3 85.24(8) . . ? O2 Zn O3 164.70(7) . . ? C5 O1 H19 111(3) . . ? Zn O2 H2W 115(3) . . ? Zn O2 H1W 121(3) . . ? H2W O2 H1W 107(4) . . ? N5 O3 Zn 122.58(15) . . ? C7 N1 C1 118.5(2) . . ? C7 N1 Zn 113.72(17) . . ? C1 N1 Zn 127.80(16) . . ? C13 N2 C3 118.6(2) . . ? C13 N2 Zn 112.53(17) . . ? C3 N2 Zn 127.87(16) . . ? C12 N3 C8 117.8(2) . . ? C12 N3 Zn 130.74(17) . . ? C8 N3 Zn 111.50(16) . . ? C18 N4 C14 118.0(2) . . ? C18 N4 Zn 129.83(16) . . ? C14 N4 Zn 112.00(15) . . ? O4 N5 O5 120.6(2) . . ? O4 N5 O3 120.3(2) . . ? O5 N5 O3 119.2(2) . . ? N1 C1 C6 110.6(2) . . ? N1 C1 C2 110.1(2) . . ? C6 C1 C2 111.5(2) . . ? N1 C1 H1 108.2 . . ? C6 C1 H1 108.2 . . ? C2 C1 H1 108.2 . . ? C1 C2 C3 114.1(2) . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2B 108.7 . . ? C3 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? N2 C3 C4 110.0(2) . . ? N2 C3 C2 109.5(2) . . ? C4 C3 C2 111.2(2) . . ? N2 C3 H3 108.7 . . ? C4 C3 H3 108.7 . . ? C2 C3 H3 108.7 . . ? C5 C4 C3 112.5(2) . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? O1 C5 C4 111.0(2) . . ? O1 C5 C6 105.8(2) . . ? C4 C5 C6 110.4(2) . . ? O1 C5 H5 109.9 . . ? C4 C5 H5 109.9 . . ? C6 C5 H5 109.9 . . ? C1 C6 C5 112.8(2) . . ? C1 C6 H6A 109.0 . . ? C5 C6 H6A 109.0 . . ? C1 C6 H6B 109.0 . . ? C5 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? N1 C7 C8 119.9(2) . . ? N1 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? N3 C8 C9 122.5(2) . . ? N3 C8 C7 115.9(2) . . ? C9 C8 C7 121.5(2) . . ? C8 C9 C10 118.9(2) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 118.8(2) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C10 C11 C12 119.1(2) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? N3 C12 C11 122.9(2) . . ? N3 C12 H12 118.6 . . ? C11 C12 H12 118.6 . . ? N2 C13 C14 120.0(2) . . ? N2 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? N4 C14 C15 122.4(2) . . ? N4 C14 C13 116.0(2) . . ? C15 C14 C13 121.6(2) . . ? C16 C15 C14 118.5(2) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C17 C16 C15 119.4(2) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 118.7(2) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? N4 C18 C17 122.9(2) . . ? N4 C18 H18 118.6 . . ? C17 C18 H18 118.6 . . ? O7 N6 O8 118.7(3) . . ? O7 N6 O6 123.4(3) . . ? O8 N6 O6 117.9(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Zn O3 N5 38.45(19) . . . . ? N4 Zn O3 N5 -154.09(18) . . . . ? N2 Zn O3 N5 128.43(18) . . . . ? N3 Zn O3 N5 -39.37(18) . . . . ? O2 Zn O3 N5 -113.6(3) . . . . ? N4 Zn N1 C7 -174.9(3) . . . . ? N2 Zn N1 C7 -177.7(2) . . . . ? N3 Zn N1 C7 3.5(2) . . . . ? O2 Zn N1 C7 93.0(2) . . . . ? O3 Zn N1 C7 -79.9(2) . . . . ? N4 Zn N1 C1 6.6(5) . . . . ? N2 Zn N1 C1 3.8(2) . . . . ? N3 Zn N1 C1 -175.0(2) . . . . ? O2 Zn N1 C1 -85.5(2) . . . . ? O3 Zn N1 C1 101.7(2) . . . . ? N1 Zn N2 C13 -172.90(19) . . . . ? N4 Zn N2 C13 7.71(19) . . . . ? N3 Zn N2 C13 -167.5(3) . . . . ? O2 Zn N2 C13 -77.96(19) . . . . ? O3 Zn N2 C13 88.56(19) . . . . ? N1 Zn N2 C3 -4.9(2) . . . . ? N4 Zn N2 C3 175.7(2) . . . . ? N3 Zn N2 C3 0.5(5) . . . . ? O2 Zn N2 C3 90.0(2) . . . . ? O3 Zn N2 C3 -103.4(2) . . . . ? N1 Zn N3 C12 174.7(3) . . . . ? N4 Zn N3 C12 -5.7(3) . . . . ? N2 Zn N3 C12 169.1(3) . . . . ? O2 Zn N3 C12 79.8(3) . . . . ? O3 Zn N3 C12 -85.5(3) . . . . ? N1 Zn N3 C8 -4.77(18) . . . . ? N4 Zn N3 C8 174.85(17) . . . . ? N2 Zn N3 C8 -10.3(5) . . . . ? O2 Zn N3 C8 -99.70(18) . . . . ? O3 Zn N3 C8 95.02(18) . . . . ? N1 Zn N4 C18 175.5(3) . . . . ? N2 Zn N4 C18 178.3(3) . . . . ? N3 Zn N4 C18 -2.9(3) . . . . ? O2 Zn N4 C18 -91.5(2) . . . . ? O3 Zn N4 C18 78.6(2) . . . . ? N1 Zn N4 C14 -8.7(5) . . . . ? N2 Zn N4 C14 -5.89(17) . . . . ? N3 Zn N4 C14 172.97(16) . . . . ? O2 Zn N4 C14 84.35(17) . . . . ? O3 Zn N4 C14 -105.55(17) . . . . ? Zn O3 N5 O4 -48.6(3) . . . . ? Zn O3 N5 O5 131.1(2) . . . . ? C7 N1 C1 C6 87.6(3) . . . . ? Zn N1 C1 C6 -94.0(2) . . . . ? C7 N1 C1 C2 -148.8(3) . . . . ? Zn N1 C1 C2 29.6(3) . . . . ? N1 C1 C2 C3 -73.7(3) . . . . ? C6 C1 C2 C3 49.4(3) . . . . ? C13 N2 C3 C4 -97.5(3) . . . . ? Zn N2 C3 C4 95.1(2) . . . . ? C13 N2 C3 C2 140.0(2) . . . . ? Zn N2 C3 C2 -27.4(3) . . . . ? C1 C2 C3 N2 72.1(3) . . . . ? C1 C2 C3 C4 -49.7(3) . . . . ? N2 C3 C4 C5 -68.4(3) . . . . ? C2 C3 C4 C5 53.1(3) . . . . ? C3 C4 C5 O1 -173.3(2) . . . . ? C3 C4 C5 C6 -56.4(3) . . . . ? N1 C1 C6 C5 70.3(3) . . . . ? C2 C1 C6 C5 -52.5(3) . . . . ? O1 C5 C6 C1 176.3(2) . . . . ? C4 C5 C6 C1 56.1(3) . . . . ? C1 N1 C7 C8 177.0(2) . . . . ? Zn N1 C7 C8 -1.7(3) . . . . ? C12 N3 C8 C9 2.5(4) . . . . ? Zn N3 C8 C9 -177.9(2) . . . . ? C12 N3 C8 C7 -174.1(2) . . . . ? Zn N3 C8 C7 5.4(3) . . . . ? N1 C7 C8 N3 -2.7(4) . . . . ? N1 C7 C8 C9 -179.4(3) . . . . ? N3 C8 C9 C10 -2.5(4) . . . . ? C7 C8 C9 C10 174.0(3) . . . . ? C8 C9 C10 C11 -0.1(4) . . . . ? C9 C10 C11 C12 2.4(4) . . . . ? C8 N3 C12 C11 -0.1(4) . . . . ? Zn N3 C12 C11 -179.5(2) . . . . ? C10 C11 C12 N3 -2.4(5) . . . . ? C3 N2 C13 C14 -177.6(2) . . . . ? Zn N2 C13 C14 -8.4(3) . . . . ? C18 N4 C14 C15 0.1(4) . . . . ? Zn N4 C14 C15 -176.3(2) . . . . ? C18 N4 C14 C13 -180.0(2) . . . . ? Zn N4 C14 C13 3.7(3) . . . . ? N2 C13 C14 N4 3.3(4) . . . . ? N2 C13 C14 C15 -176.7(2) . . . . ? N4 C14 C15 C16 0.1(4) . . . . ? C13 C14 C15 C16 -179.8(2) . . . . ? C14 C15 C16 C17 0.1(4) . . . . ? C15 C16 C17 C18 -0.5(4) . . . . ? C14 N4 C18 C17 -0.5(4) . . . . ? Zn N4 C18 C17 175.1(2) . . . . ? C16 C17 C18 N4 0.8(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H19 O8 0.87(4) 2.56(4) 3.191(4) 131(4) 1_655 O1 H19 O6 0.87(4) 2.07(4) 2.919(4) 168(4) 1_655 O2 H1W O7 0.83(3) 2.51(3) 3.236(5) 147(3) 1_545 O2 H1W O8 0.83(3) 2.15(3) 2.912(4) 153(4) 1_545 O2 H2W O5 0.80(3) 1.95(3) 2.737(3) 166(4) 1_545 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.897 _refine_diff_density_min -0.667 _refine_diff_density_rms 0.070 # === END data_compound4 _database_code_depnum_ccdc_archive 'CCDC 828955' #TrackingRef '- CoCu-allstructures-rev.cif' _publ_section_exptl_refinement ; The structure was solved by direct methods. All non-H atoms were refined anisotropically. H atoms were included in calculated positions, except those bonded to O1 and O2, which were found by difference Fourier techniques and refined isotropically, with restraints on the bond lengths. The copper and cobalt atoms were restrained to occupy the same site with the same Uij values. Their occupancies were fixed at 0.6 and 0.4, respectively, as established from ICP-OES elemental analysis data and magnetic measurements. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 Co0.40 Cu0.60 N5 O5, N O3' _chemical_formula_sum 'C18 H22 Co0.40 Cu0.60 N6 O8' _chemical_formula_weight 512.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.0170(2) _cell_length_b 7.35720(10) _cell_length_c 29.4159(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.0450(10) _cell_angle_gamma 90.00 _cell_volume 2049.20(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 22596 _cell_measurement_theta_min 1.51 _cell_measurement_theta_max 26.022 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1057 _exptl_absorpt_coefficient_mu 1.037 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8195 _exptl_absorpt_correction_T_max 0.9034 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ? _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16129 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.03 _reflns_number_total 4032 _reflns_number_gt 3551 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material 'SHELXTL (Bruker, 2001)' _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^)+(0.0284P)^2^+2.2889P] 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 4032 _refine_ls_number_parameters 310 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0812 _refine_ls_wR_factor_gt 0.0782 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.89721(3) 0.20875(4) 0.874894(9) 0.02305(10) Uani 0.60 1 d P . . Co1 Co 0.89721(3) 0.20875(4) 0.874894(9) 0.02305(10) Uani 0.40 1 d P . . O1 O 1.36343(19) 0.4330(3) 0.86113(7) 0.0364(4) Uani 1 1 d D . . O2 O 0.81145(19) -0.0667(3) 0.89069(7) 0.0386(4) Uani 1 1 d D . . O3 O 0.92939(18) 0.5325(2) 0.86515(6) 0.0345(4) Uani 1 1 d . . . O4 O 0.9587(2) 0.5324(3) 0.79533(7) 0.0448(5) Uani 1 1 d . . . O5 O 0.8311(2) 0.7394(3) 0.81267(7) 0.0425(5) Uani 1 1 d . . . N1 N 0.97369(18) 0.1199(3) 0.82320(6) 0.0220(4) Uani 1 1 d . . . N2 N 1.08369(19) 0.1543(3) 0.92740(6) 0.0231(4) Uani 1 1 d . . . N3 N 0.71769(19) 0.2397(3) 0.81486(7) 0.0247(4) Uani 1 1 d . . . N4 N 0.84834(19) 0.3007(3) 0.93437(6) 0.0230(4) Uani 1 1 d . . . N6 N 0.9066(2) 0.6006(3) 0.82404(7) 0.0276(4) Uani 1 1 d . . . C1 C 1.1134(2) 0.0376(3) 0.83013(8) 0.0243(5) Uani 1 1 d . . . H1 H 1.1029 -0.0538 0.8040 0.029 Uiso 1 1 calc R . . C2 C 1.1654(2) -0.0612(3) 0.87825(8) 0.0253(5) Uani 1 1 d . . . H2A H 1.2464 -0.1394 0.8789 0.030 Uiso 1 1 calc R . . H2B H 1.0891 -0.1411 0.8812 0.030 Uiso 1 1 calc R . . C3 C 1.2110(2) 0.0675(3) 0.92157(8) 0.0249(5) Uani 1 1 d . . . H3 H 1.2593 -0.0052 0.9511 0.030 Uiso 1 1 calc R . . C4 C 1.3139(2) 0.2130(3) 0.91560(8) 0.0264(5) Uani 1 1 d . . . H4A H 1.3328 0.3011 0.9424 0.032 Uiso 1 1 calc R . . H4B H 1.4046 0.1543 0.9176 0.032 Uiso 1 1 calc R . . C5 C 1.2580(2) 0.3145(3) 0.86828(8) 0.0270(5) Uani 1 1 d . . . H5 H 1.1732 0.3872 0.8678 0.032 Uiso 1 1 calc R . . C6 C 1.2184(2) 0.1826(3) 0.82608(8) 0.0278(5) Uani 1 1 d . . . H6A H 1.3050 0.1222 0.8244 0.033 Uiso 1 1 calc R . . H6B H 1.1766 0.2515 0.7959 0.033 Uiso 1 1 calc R . . C7 C 0.8886(2) 0.1387(3) 0.78081(8) 0.0269(5) Uani 1 1 d . . . H7 H 0.9169 0.1082 0.7539 0.032 Uiso 1 1 calc R . . C8 C 0.7465(2) 0.2076(3) 0.77378(8) 0.0245(5) Uani 1 1 d . . . C9 C 0.6477(3) 0.2278(4) 0.72880(9) 0.0334(6) Uani 1 1 d . . . H9 H 0.6726 0.2083 0.7007 0.040 Uiso 1 1 calc R . . C10 C 0.5111(3) 0.2770(4) 0.72532(9) 0.0353(6) Uani 1 1 d . . . H10 H 0.4409 0.2924 0.6948 0.042 Uiso 1 1 calc R . . C11 C 0.4791(3) 0.3029(3) 0.76671(9) 0.0327(6) Uani 1 1 d . . . H11 H 0.3857 0.3333 0.7653 0.039 Uiso 1 1 calc R . . C12 C 0.5851(2) 0.2842(4) 0.81085(9) 0.0326(6) Uani 1 1 d . . . H12 H 0.5622 0.3039 0.8394 0.039 Uiso 1 1 calc R . . C13 C 1.0789(2) 0.1774(3) 0.96973(8) 0.0235(5) Uani 1 1 d . . . H13 H 1.1561 0.1422 0.9970 0.028 Uiso 1 1 calc R . . C14 C 0.9523(2) 0.2593(3) 0.97580(8) 0.0213(5) Uani 1 1 d . . . C15 C 0.9420(2) 0.2933(3) 1.02072(8) 0.0258(5) Uani 1 1 d . . . H15 H 1.0173 0.2631 1.0490 0.031 Uiso 1 1 calc R . . C16 C 0.8192(2) 0.3725(3) 1.02359(8) 0.0283(5) Uani 1 1 d . . . H16 H 0.8083 0.3957 1.0540 0.034 Uiso 1 1 calc R . . C17 C 0.7134(3) 0.4168(3) 0.98171(9) 0.0315(5) Uani 1 1 d . . . H17 H 0.6285 0.4712 0.9828 0.038 Uiso 1 1 calc R . . C18 C 0.7325(2) 0.3809(3) 0.93798(8) 0.0296(5) Uani 1 1 d . . . H18 H 0.6600 0.4148 0.9093 0.036 Uiso 1 1 calc R . . O6 O 0.4509(2) 0.6959(3) 0.93884(8) 0.0544(6) Uani 1 1 d . . . O7 O 0.6159(2) 0.8993(4) 0.95769(10) 0.0821(9) Uani 1 1 d . . . O8 O 0.5270(3) 0.8103(4) 0.88566(8) 0.0700(7) Uani 1 1 d . . . N5 N 0.5333(2) 0.8027(3) 0.92794(8) 0.0355(5) Uani 1 1 d . . . H1W H 0.726(2) -0.077(5) 0.8964(12) 0.065(10) Uiso 1 1 d D . . H2W H 0.811(4) -0.151(4) 0.8675(10) 0.074(12) Uiso 1 1 d D . . H19 H 1.386(4) 0.527(4) 0.8832(10) 0.069(11) Uiso 1 1 d 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 Cu1 0.01749(14) 0.03567(18) 0.01665(14) -0.00107(12) 0.00649(11) 0.00275(12) Co1 0.01749(14) 0.03567(18) 0.01665(14) -0.00107(12) 0.00649(11) 0.00275(12) O1 0.0342(9) 0.0360(10) 0.0464(11) -0.0037(9) 0.0235(8) -0.0089(8) O2 0.0281(9) 0.0476(11) 0.0387(10) -0.0081(9) 0.0090(8) 0.0027(8) O3 0.0404(10) 0.0379(10) 0.0254(9) 0.0011(8) 0.0112(7) 0.0032(8) O4 0.0583(12) 0.0456(11) 0.0425(11) 0.0043(9) 0.0327(10) 0.0081(10) O5 0.0452(11) 0.0383(11) 0.0377(10) 0.0001(8) 0.0050(9) 0.0130(9) N1 0.0202(9) 0.0239(10) 0.0236(9) -0.0005(8) 0.0096(8) 0.0016(8) N2 0.0189(9) 0.0266(10) 0.0237(9) 0.0025(8) 0.0069(7) 0.0016(8) N3 0.0217(9) 0.0298(11) 0.0237(9) -0.0028(8) 0.0089(8) 0.0011(8) N4 0.0217(9) 0.0245(10) 0.0222(9) 0.0009(8) 0.0066(7) 0.0004(8) N6 0.0241(10) 0.0289(11) 0.0297(11) -0.0019(9) 0.0086(8) -0.0022(9) C1 0.0226(11) 0.0271(12) 0.0253(11) -0.0045(9) 0.0107(9) 0.0029(9) C2 0.0212(11) 0.0244(11) 0.0306(12) 0.0002(9) 0.0091(9) 0.0040(9) C3 0.0191(10) 0.0290(12) 0.0263(11) 0.0023(9) 0.0071(9) 0.0043(9) C4 0.0181(10) 0.0313(12) 0.0293(12) -0.0037(10) 0.0073(9) 0.0009(10) C5 0.0224(11) 0.0281(12) 0.0352(13) 0.0001(10) 0.0159(10) -0.0017(10) C6 0.0235(11) 0.0336(13) 0.0302(12) 0.0001(10) 0.0142(9) 0.0021(10) C7 0.0273(12) 0.0339(13) 0.0236(11) 0.0018(10) 0.0138(10) 0.0025(10) C8 0.0238(11) 0.0275(12) 0.0234(11) 0.0023(10) 0.0095(9) 0.0010(10) C9 0.0311(13) 0.0467(15) 0.0229(12) 0.0055(11) 0.0096(10) 0.0008(12) C10 0.0268(12) 0.0428(15) 0.0320(13) 0.0082(11) 0.0035(10) 0.0013(11) C11 0.0210(11) 0.0362(14) 0.0396(14) -0.0012(12) 0.0081(10) 0.0031(11) C12 0.0229(11) 0.0438(15) 0.0324(13) -0.0075(12) 0.0109(10) 0.0009(11) C13 0.0204(10) 0.0274(12) 0.0209(11) 0.0036(9) 0.0043(9) 0.0012(9) C14 0.0203(10) 0.0217(11) 0.0219(11) 0.0029(9) 0.0068(9) -0.0006(9) C15 0.0289(12) 0.0269(12) 0.0217(11) 0.0040(9) 0.0085(9) 0.0026(10) C16 0.0338(13) 0.0289(12) 0.0261(12) 0.0009(10) 0.0149(10) 0.0022(11) C17 0.0279(12) 0.0348(14) 0.0340(13) -0.0018(11) 0.0133(10) 0.0070(11) C18 0.0241(11) 0.0354(14) 0.0279(12) -0.0004(10) 0.0065(10) 0.0075(10) O6 0.0422(11) 0.0651(14) 0.0628(14) 0.0220(12) 0.0266(10) 0.0140(11) O7 0.0491(13) 0.0726(17) 0.0886(18) -0.0346(15) -0.0267(13) 0.0072(12) O8 0.0633(15) 0.112(2) 0.0403(12) -0.0059(13) 0.0241(11) -0.0126(15) N5 0.0261(11) 0.0385(12) 0.0374(12) 0.0000(10) 0.0042(9) 0.0075(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 Cu1 N1 2.0216(18) . ? Cu1 N2 2.0379(18) . ? Cu1 N4 2.0779(18) . ? Cu1 N3 2.0813(19) . ? Cu1 O2 2.306(2) . ? Cu1 O3 2.4332(18) . ? O1 C5 1.437(3) . ? O1 H19 0.922(19) . ? O2 H1W 0.930(15) . ? O2 H2W 0.921(15) . ? O3 N6 1.259(2) . ? O4 N6 1.235(3) . ? O5 N6 1.250(3) . ? N1 C7 1.267(3) . ? N1 C1 1.477(3) . ? N2 C13 1.273(3) . ? N2 C3 1.485(3) . ? N3 C12 1.335(3) . ? N3 C8 1.352(3) . ? N4 C18 1.337(3) . ? N4 C14 1.354(3) . ? C1 C2 1.524(3) . ? C1 C6 1.530(3) . ? C1 H1 1.0000 . ? C2 C3 1.533(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.535(3) . ? C3 H3 1.0000 . ? C4 C5 1.516(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.523(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.461(3) . ? C7 H7 0.9500 . ? C8 C9 1.378(3) . ? C9 C10 1.386(4) . ? C9 H9 0.9500 . ? C10 C11 1.369(3) . ? C10 H10 0.9500 . ? C11 C12 1.390(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.466(3) . ? C13 H13 0.9500 . ? C14 C15 1.382(3) . ? C15 C16 1.388(3) . ? C15 H15 0.9500 . ? C16 C17 1.377(3) . ? C16 H16 0.9500 . ? C17 C18 1.386(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? O6 N5 1.254(3) . ? O7 N5 1.218(3) . ? O8 N5 1.226(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 91.60(7) . . ? N1 Cu1 N4 171.85(7) . . ? N2 Cu1 N4 80.52(7) . . ? N1 Cu1 N3 80.31(7) . . ? N2 Cu1 N3 171.56(7) . . ? N4 Cu1 N3 107.64(7) . . ? N1 Cu1 O2 97.18(7) . . ? N2 Cu1 O2 89.09(7) . . ? N4 Cu1 O2 84.89(7) . . ? N3 Cu1 O2 89.52(7) . . ? N1 Cu1 O3 97.50(7) . . ? N2 Cu1 O3 99.09(7) . . ? N4 Cu1 O3 81.79(7) . . ? N3 Cu1 O3 84.48(7) . . ? O2 Cu1 O3 162.96(6) . . ? C5 O1 H19 112(2) . . ? Cu1 O2 H1W 122(2) . . ? Cu1 O2 H2W 111(2) . . ? H1W O2 H2W 107(3) . . ? N6 O3 Cu1 120.88(14) . . ? C7 N1 C1 118.89(18) . . ? C7 N1 Cu1 113.99(15) . . ? C1 N1 Cu1 127.11(14) . . ? C13 N2 C3 118.56(18) . . ? C13 N2 Cu1 113.42(15) . . ? C3 N2 Cu1 127.32(14) . . ? C12 N3 C8 117.4(2) . . ? C12 N3 Cu1 131.37(16) . . ? C8 N3 Cu1 111.22(14) . . ? C18 N4 C14 117.43(19) . . ? C18 N4 Cu1 131.29(15) . . ? C14 N4 Cu1 111.15(14) . . ? O4 N6 O5 120.2(2) . . ? O4 N6 O3 120.7(2) . . ? O5 N6 O3 119.1(2) . . ? N1 C1 C2 110.19(17) . . ? N1 C1 C6 110.34(18) . . ? C2 C1 C6 111.68(19) . . ? N1 C1 H1 108.2 . . ? C2 C1 H1 108.2 . . ? C6 C1 H1 108.2 . . ? C1 C2 C3 113.37(19) . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? N2 C3 C2 109.11(18) . . ? N2 C3 C4 110.34(19) . . ? C2 C3 C4 111.38(19) . . ? N2 C3 H3 108.7 . . ? C2 C3 H3 108.7 . . ? C4 C3 H3 108.7 . . ? C5 C4 C3 112.79(18) . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4B 109.0 . . ? C3 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? O1 C5 C4 111.35(19) . . ? O1 C5 C6 106.01(18) . . ? C4 C5 C6 110.8(2) . . ? O1 C5 H5 109.5 . . ? C4 C5 H5 109.5 . . ? C6 C5 H5 109.5 . . ? C5 C6 C1 112.57(18) . . ? C5 C6 H6A 109.1 . . ? C1 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C1 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? N1 C7 C8 119.2(2) . . ? N1 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? N3 C8 C9 122.9(2) . . ? N3 C8 C7 114.62(19) . . ? C9 C8 C7 122.3(2) . . ? C8 C9 C10 118.8(2) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 118.8(2) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C10 C11 C12 119.2(2) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? N3 C12 C11 122.7(2) . . ? N3 C12 H12 118.6 . . ? C11 C12 H12 118.6 . . ? N2 C13 C14 118.93(19) . . ? N2 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? N4 C14 C15 122.9(2) . . ? N4 C14 C13 115.14(19) . . ? C15 C14 C13 121.9(2) . . ? C14 C15 C16 118.6(2) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C17 C16 C15 118.9(2) . . ? C17 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? C16 C17 C18 119.1(2) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? N4 C18 C17 123.0(2) . . ? N4 C18 H18 118.5 . . ? C17 C18 H18 118.5 . . ? O7 N5 O8 120.0(3) . . ? O7 N5 O6 122.1(3) . . ? O8 N5 O6 117.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 O3 N6 38.44(17) . . . . ? N2 Cu1 O3 N6 131.28(16) . . . . ? N4 Cu1 O3 N6 -149.76(17) . . . . ? N3 Cu1 O3 N6 -41.00(16) . . . . ? O2 Cu1 O3 N6 -110.9(2) . . . . ? N2 Cu1 N1 C7 -176.43(18) . . . . ? N4 Cu1 N1 C7 -161.5(5) . . . . ? N3 Cu1 N1 C7 6.00(17) . . . . ? O2 Cu1 N1 C7 94.28(17) . . . . ? O3 Cu1 N1 C7 -77.05(18) . . . . ? N2 Cu1 N1 C1 4.01(18) . . . . ? N4 Cu1 N1 C1 19.0(6) . . . . ? N3 Cu1 N1 C1 -173.55(19) . . . . ? O2 Cu1 N1 C1 -85.27(18) . . . . ? O3 Cu1 N1 C1 103.39(18) . . . . ? N1 Cu1 N2 C13 -174.01(17) . . . . ? N4 Cu1 N2 C13 8.12(16) . . . . ? N3 Cu1 N2 C13 -157.4(5) . . . . ? O2 Cu1 N2 C13 -76.85(17) . . . . ? O3 Cu1 N2 C13 88.13(17) . . . . ? N1 Cu1 N2 C3 -3.86(19) . . . . ? N4 Cu1 N2 C3 178.27(19) . . . . ? N3 Cu1 N2 C3 12.7(6) . . . . ? O2 Cu1 N2 C3 93.30(18) . . . . ? O3 Cu1 N2 C3 -101.72(18) . . . . ? N1 Cu1 N3 C12 173.0(2) . . . . ? N2 Cu1 N3 C12 156.1(5) . . . . ? N4 Cu1 N3 C12 -8.9(2) . . . . ? O2 Cu1 N3 C12 75.6(2) . . . . ? O3 Cu1 N3 C12 -88.4(2) . . . . ? N1 Cu1 N3 C8 -7.03(16) . . . . ? N2 Cu1 N3 C8 -23.9(6) . . . . ? N4 Cu1 N3 C8 171.12(15) . . . . ? O2 Cu1 N3 C8 -104.40(16) . . . . ? O3 Cu1 N3 C8 91.57(16) . . . . ? N1 Cu1 N4 C18 161.8(5) . . . . ? N2 Cu1 N4 C18 177.0(2) . . . . ? N3 Cu1 N4 C18 -5.2(2) . . . . ? O2 Cu1 N4 C18 -93.1(2) . . . . ? O3 Cu1 N4 C18 76.3(2) . . . . ? N1 Cu1 N4 C14 -22.5(6) . . . . ? N2 Cu1 N4 C14 -7.30(15) . . . . ? N3 Cu1 N4 C14 170.50(14) . . . . ? O2 Cu1 N4 C14 82.63(15) . . . . ? O3 Cu1 N4 C14 -108.01(15) . . . . ? Cu1 O3 N6 O4 -49.7(3) . . . . ? Cu1 O3 N6 O5 130.78(18) . . . . ? C7 N1 C1 C2 -150.5(2) . . . . ? Cu1 N1 C1 C2 29.0(3) . . . . ? C7 N1 C1 C6 85.7(2) . . . . ? Cu1 N1 C1 C6 -94.8(2) . . . . ? N1 C1 C2 C3 -72.2(2) . . . . ? C6 C1 C2 C3 50.8(2) . . . . ? C13 N2 C3 C2 140.8(2) . . . . ? Cu1 N2 C3 C2 -28.9(3) . . . . ? C13 N2 C3 C4 -96.5(2) . . . . ? Cu1 N2 C3 C4 93.8(2) . . . . ? C1 C2 C3 N2 71.6(2) . . . . ? C1 C2 C3 C4 -50.4(2) . . . . ? N2 C3 C4 C5 -68.7(2) . . . . ? C2 C3 C4 C5 52.6(3) . . . . ? C3 C4 C5 O1 -172.71(18) . . . . ? C3 C4 C5 C6 -55.0(2) . . . . ? O1 C5 C6 C1 176.08(18) . . . . ? C4 C5 C6 C1 55.1(2) . . . . ? N1 C1 C6 C5 69.8(2) . . . . ? C2 C1 C6 C5 -53.1(3) . . . . ? C1 N1 C7 C8 175.6(2) . . . . ? Cu1 N1 C7 C8 -4.0(3) . . . . ? C12 N3 C8 C9 3.3(4) . . . . ? Cu1 N3 C8 C9 -176.7(2) . . . . ? C12 N3 C8 C7 -173.0(2) . . . . ? Cu1 N3 C8 C7 7.0(3) . . . . ? N1 C7 C8 N3 -2.2(3) . . . . ? N1 C7 C8 C9 -178.6(2) . . . . ? N3 C8 C9 C10 -2.3(4) . . . . ? C7 C8 C9 C10 173.7(2) . . . . ? C8 C9 C10 C11 -0.3(4) . . . . ? C9 C10 C11 C12 1.8(4) . . . . ? C8 N3 C12 C11 -1.8(4) . . . . ? Cu1 N3 C12 C11 178.24(19) . . . . ? C10 C11 C12 N3 -0.8(4) . . . . ? C3 N2 C13 C14 -178.67(19) . . . . ? Cu1 N2 C13 C14 -7.6(3) . . . . ? C18 N4 C14 C15 1.2(3) . . . . ? Cu1 N4 C14 C15 -175.20(18) . . . . ? C18 N4 C14 C13 -177.9(2) . . . . ? Cu1 N4 C14 C13 5.7(2) . . . . ? N2 C13 C14 N4 1.2(3) . . . . ? N2 C13 C14 C15 -178.0(2) . . . . ? N4 C14 C15 C16 0.4(4) . . . . ? C13 C14 C15 C16 179.5(2) . . . . ? C14 C15 C16 C17 -1.0(4) . . . . ? C15 C16 C17 C18 0.1(4) . . . . ? C14 N4 C18 C17 -2.2(4) . . . . ? Cu1 N4 C18 C17 173.30(19) . . . . ? C16 C17 C18 N4 1.6(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H1W O8 0.930(15) 2.08(2) 2.947(3) 154(3) 1_545 O2 H1W O7 0.930(15) 2.41(2) 3.210(4) 145(3) 1_545 O2 H2W O5 0.921(15) 1.872(18) 2.763(3) 162(3) 1_545 O2 H2W O3 0.921(15) 2.62(3) 3.352(3) 136(3) 1_545 O1 H19 O6 0.922(19) 1.989(19) 2.903(3) 170(3) 1_655 O1 H19 O8 0.922(19) 2.51(3) 3.184(3) 130(3) 1_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.735 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.056