# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 186/1308 data_1 _publ_contact_author 'Igor O.Fritsky' _publ_contact_author_email 'kokozay@chem.kiev.ua' loop_ _publ_author_name ; H. Kozlowski, I.O. Fritsky, A. Dobosz, A. Karaczyn, N.M. Dudarenko, T.Yu. Sliva, T. Glowiak, J. Swiatek-Kozlowska ; _journal_name_full 'J.Chem.Soc., Dalton Trans.' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [(aqua)(1,10-phenantroline){2-(hydroxyimino)propanoato (2-)}copper(II)] tetrahydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 Cu N3 O8' _chemical_formula_weight 434.89 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' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1180(10) _cell_length_b 11.377(2) _cell_length_c 12.616(3) _cell_angle_alpha 70.91(3) _cell_angle_beta 82.79(3) _cell_angle_gamma 78.15(3) _cell_volume 943.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'BLOCK' _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 450 _exptl_absorpt_coefficient_mu 1.206 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Kuma KM4 automatic diffractometer' _diffrn_measurement_method 'profile data from omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6936 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 28.76 _reflns_number_total 4305 _reflns_number_gt 3802 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'ORTEP, 1964' _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^)+(0.0617P)^2^+0.5687P] 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 SHELXL _refine_ls_extinction_coef 0.0015(16) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4305 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1056 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.101 _refine_ls_shift/su_mean 0.004 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 Cu Cu 0.46979(4) 0.39306(2) 0.76693(2) 0.03526(11) Uani 1 1 d . . . O1 O 0.6172(3) 0.46771(15) 0.62714(14) 0.0437(4) Uani 1 1 d . . . O2 O 0.8230(3) 0.41184(18) 0.49686(15) 0.0506(4) Uani 1 1 d . . . O3 O 0.5993(2) 0.11920(15) 0.81267(15) 0.0440(4) Uani 1 1 d . . . O4 O 0.1987(3) 0.38233(16) 0.69741(14) 0.0449(4) Uani 1 1 d . . . O5 O 0.1910(3) 0.32289(19) 0.41646(19) 0.0607(5) Uani 1 1 d . . . O6 O 1.0372(4) -0.0620(4) 1.1069(2) 0.0745(8) Uani 1 1 d . . . O7 O 0.7429(3) -0.1155(2) 1.26215(19) 0.0623(5) Uani 1 1 d . . . O8 O 0.6551(5) -0.0746(3) 1.4656(2) 0.0924(9) Uani 1 1 d . . . N1 N 0.6134(3) 0.23480(17) 0.74497(15) 0.0349(4) Uani 1 1 d . . . N2 N 0.3838(3) 0.33368(18) 0.93273(16) 0.0363(4) Uani 1 1 d . . . N3 N 0.3571(3) 0.56259(17) 0.78454(16) 0.0362(4) Uani 1 1 d . . . C1 C 0.7216(3) 0.3852(2) 0.58575(19) 0.0380(4) Uani 1 1 d . . . C2 C 0.7179(3) 0.2498(2) 0.65088(19) 0.0382(4) Uani 1 1 d . . . C3 C 0.8210(4) 0.1431(3) 0.6106(2) 0.0511(6) Uani 1 1 d . . . H3A H 0.9120 0.0896 0.6638 0.077 Uiso 1 1 calc R . . H3B H 0.8874 0.1758 0.5391 0.077 Uiso 1 1 calc R . . H3C H 0.7299 0.0952 0.6029 0.077 Uiso 1 1 calc R . . C4 C 0.3944(4) 0.2176(2) 1.0042(2) 0.0439(5) Uani 1 1 d . . . H4A H 0.4452 0.1494 0.9779 0.053 Uiso 1 1 calc R . . C5 C 0.3318(4) 0.1941(3) 1.1176(2) 0.0497(6) Uani 1 1 d . . . H5A H 0.3412 0.1114 1.1654 0.060 Uiso 1 1 calc R . . C6 C 0.2567(4) 0.2926(3) 1.1581(2) 0.0475(6) Uani 1 1 d . . . H6A H 0.2161 0.2777 1.2336 0.057 Uiso 1 1 calc R . . C7 C 0.2413(3) 0.4171(2) 1.0843(2) 0.0401(5) Uani 1 1 d . . . C8 C 0.3076(3) 0.4325(2) 0.97192(18) 0.0346(4) Uani 1 1 d . . . C9 C 0.3402(4) 0.6751(2) 0.7071(2) 0.0433(5) Uani 1 1 d . . . H9A H 0.3844 0.6802 0.6335 0.052 Uiso 1 1 calc R . . C10 C 0.2583(4) 0.7861(2) 0.7322(3) 0.0541(6) Uani 1 1 d . . . H10A H 0.2463 0.8634 0.6755 0.065 Uiso 1 1 calc R . . C11 C 0.1958(4) 0.7806(2) 0.8405(3) 0.0516(6) Uani 1 1 d . . . H11A H 0.1432 0.8543 0.8581 0.062 Uiso 1 1 calc R . . C12 C 0.2114(3) 0.6633(2) 0.9248(2) 0.0426(5) Uani 1 1 d . . . C13 C 0.2926(3) 0.5561(2) 0.89174(19) 0.0348(4) Uani 1 1 d . . . C15 C 0.1602(3) 0.5279(3) 1.1167(2) 0.0487(6) Uani 1 1 d . . . H15A H 0.1165 0.5190 1.1910 0.058 Uiso 1 1 calc R . . C14 C 0.1462(3) 0.6446(3) 1.0411(2) 0.0496(6) Uani 1 1 d . . . H14A H 0.0934 0.7144 1.0646 0.059 Uiso 1 1 calc R . . H1 H 0.2073 0.3081 0.7004 0.050 Uiso 1 1 d . . . H2 H 0.1830 0.4246 0.6337 0.050 Uiso 1 1 d . . . H3 H 0.0765 0.3513 0.4411 0.050 Uiso 1 1 d . . . H4 H 0.2588 0.3872 0.4116 0.050 Uiso 1 1 d . . . H7 H 0.6308 -0.1068 1.2226 0.050 Uiso 1 1 d . . . H8 H 0.8624 -0.1025 1.1983 0.050 Uiso 1 1 d . . . H9 H 0.6903 -0.1410 1.5230 0.050 Uiso 1 1 d . . . H10 H 0.5456 -0.0366 1.4889 0.050 Uiso 0.50 1 d P . . H10' H 0.6768 -0.0854 1.4050 0.050 Uiso 0.50 1 d P . . H5 H 1.1573 -0.0853 1.1261 0.050 Uiso 1 1 d . . . H6 H 1.0340 -0.0229 1.0351 0.050 Uiso 0.50 1 d P . . H6' H 1.044(12) -0.006(7) 1.097(7) 0.05(3) Uiso 0.50 1 d P . . 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 Cu 0.03782(16) 0.03060(16) 0.03523(16) -0.01033(11) 0.00196(10) -0.00369(10) O1 0.0469(9) 0.0352(8) 0.0440(9) -0.0102(7) 0.0085(7) -0.0067(7) O2 0.0501(10) 0.0505(10) 0.0411(9) -0.0087(8) 0.0108(7) -0.0038(8) O3 0.0464(9) 0.0308(8) 0.0482(9) -0.0065(7) 0.0007(7) -0.0044(6) O4 0.0483(9) 0.0416(9) 0.0430(9) -0.0113(7) -0.0055(7) -0.0054(7) O5 0.0578(11) 0.0480(10) 0.0720(13) -0.0221(10) 0.0187(10) -0.0073(9) O6 0.0553(13) 0.099(3) 0.0515(13) -0.0044(15) -0.0086(9) -0.0020(15) O7 0.0570(12) 0.0671(13) 0.0666(13) -0.0198(11) -0.0038(10) -0.0209(10) O8 0.112(2) 0.0705(16) 0.0695(15) -0.0170(13) 0.0072(15) 0.0253(14) N1 0.0344(8) 0.0300(8) 0.0374(9) -0.0088(7) -0.0019(7) -0.0026(7) N2 0.0368(9) 0.0356(9) 0.0375(9) -0.0138(8) -0.0003(7) -0.0058(7) N3 0.0361(9) 0.0327(9) 0.0397(9) -0.0122(8) -0.0027(7) -0.0044(7) C1 0.0340(10) 0.0416(11) 0.0365(10) -0.0105(9) -0.0003(8) -0.0060(8) C2 0.0334(10) 0.0394(11) 0.0411(11) -0.0145(9) -0.0017(8) -0.0019(8) C3 0.0555(14) 0.0466(13) 0.0504(14) -0.0218(11) 0.0062(11) -0.0015(11) C4 0.0485(13) 0.0400(12) 0.0409(12) -0.0111(10) -0.0003(9) -0.0069(9) C5 0.0566(14) 0.0473(13) 0.0404(12) -0.0051(10) 0.0003(10) -0.0144(11) C6 0.0444(12) 0.0622(15) 0.0361(11) -0.0134(11) 0.0025(9) -0.0155(11) C7 0.0310(10) 0.0539(13) 0.0411(11) -0.0210(10) 0.0017(8) -0.0120(9) C8 0.0274(9) 0.0413(11) 0.0395(11) -0.0175(9) -0.0008(8) -0.0080(8) C9 0.0446(12) 0.0358(11) 0.0462(12) -0.0093(10) -0.0028(10) -0.0053(9) C10 0.0577(15) 0.0337(12) 0.0656(17) -0.0098(11) -0.0070(13) -0.0037(10) C11 0.0461(13) 0.0364(12) 0.0752(18) -0.0254(12) -0.0015(12) -0.0015(10) C12 0.0326(10) 0.0443(12) 0.0592(14) -0.0284(11) 0.0003(9) -0.0064(9) C13 0.0277(9) 0.0358(10) 0.0431(11) -0.0165(9) -0.0012(8) -0.0044(7) C15 0.0378(11) 0.0696(17) 0.0493(13) -0.0352(13) 0.0067(10) -0.0110(11) C14 0.0384(12) 0.0591(15) 0.0639(16) -0.0402(14) 0.0040(11) -0.0064(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 Cu O1 1.9634(18) . ? Cu N1 1.9655(19) . ? Cu N3 2.0032(19) . ? Cu N2 2.032(2) . ? Cu O4 2.2582(18) . ? Cu O7 3.906(2) 2_657 ? Cu O2 3.919(2) 2_666 ? O1 C1 1.282(3) . ? O2 C1 1.239(3) . ? O3 N1 1.329(2) . ? O4 H1 0.8227 . ? O4 H2 0.7984 . ? O5 H3 0.8713 . ? O5 H4 0.9383 . ? O6 H5 0.8809 . ? O6 H6 0.8698 . ? O6 H6' 0.62(7) . ? O7 H7 0.9649 . ? O7 H8 1.0935 . ? O8 H9 0.8762 . ? O8 H10 0.8761 . ? O8 H10' 0.8049 . ? N1 C2 1.300(3) . ? N2 C4 1.327(3) . ? N2 C8 1.360(3) . ? N3 C9 1.325(3) . ? N3 C13 1.356(3) . ? C1 C2 1.494(3) . ? C2 C3 1.488(3) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.399(3) . ? C4 H4A 0.9300 . ? C5 C6 1.365(4) . ? C5 H5A 0.9300 . ? C6 C7 1.408(4) . ? C6 H6A 0.9300 . ? C7 C8 1.403(3) . ? C7 C15 1.437(4) . ? C8 C13 1.431(3) . ? C9 C10 1.396(4) . ? C9 H9A 0.9300 . ? C10 C11 1.368(4) . ? C10 H10A 0.9300 . ? C11 C12 1.402(4) . ? C11 H11A 0.9300 . ? C12 C13 1.405(3) . ? C12 C14 1.442(4) . ? C15 C14 1.350(4) . ? C15 H15A 0.9300 . ? C14 H14A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu N1 82.23(8) . . ? O1 Cu N3 92.39(8) . . ? N1 Cu N3 172.34(7) . . ? O1 Cu N2 161.13(8) . . ? N1 Cu N2 101.34(8) . . ? N3 Cu N2 82.03(8) . . ? O1 Cu O4 100.48(7) . . ? N1 Cu O4 94.40(7) . . ? N3 Cu O4 91.95(7) . . ? N2 Cu O4 97.73(7) . . ? O1 Cu O7 109.52(7) . 2_657 ? N1 Cu O7 52.79(6) . 2_657 ? N3 Cu O7 134.67(6) . 2_657 ? N2 Cu O7 86.74(7) . 2_657 ? O4 Cu O7 46.30(6) . 2_657 ? O1 Cu O2 62.94(6) . 2_666 ? N1 Cu O2 109.45(7) . 2_666 ? N3 Cu O2 72.49(7) . 2_666 ? N2 Cu O2 130.89(6) . 2_666 ? O4 Cu O2 43.92(6) . 2_666 ? O7 Cu O2 82.76(5) 2_657 2_666 ? C1 O1 Cu 113.26(14) . . ? Cu O4 H1 105.9 . . ? Cu O4 H2 115.5 . . ? H1 O4 H2 107.4 . . ? H3 O5 H4 102.2 . . ? H5 O6 H6 110.0 . . ? H5 O6 H6' 89.6 . . ? H6 O6 H6' 70.2 . . ? H7 O7 H8 106.1 . . ? H9 O8 H10 104.9 . . ? H9 O8 H10' 115.4 . . ? H10 O8 H10' 125.0 . . ? C2 N1 O3 120.03(18) . . ? C2 N1 Cu 114.22(15) . . ? O3 N1 Cu 125.54(14) . . ? C4 N2 C8 118.3(2) . . ? C4 N2 Cu 130.06(16) . . ? C8 N2 Cu 111.66(15) . . ? C9 N3 C13 118.3(2) . . ? C9 N3 Cu 128.76(17) . . ? C13 N3 Cu 112.89(15) . . ? O2 C1 O1 123.9(2) . . ? O2 C1 C2 119.5(2) . . ? O1 C1 C2 116.59(19) . . ? N1 C2 C3 123.5(2) . . ? N1 C2 C1 113.35(19) . . ? C3 C2 C1 123.1(2) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 C5 122.4(2) . . ? N2 C4 H4A 118.8 . . ? C5 C4 H4A 118.8 . . ? C6 C5 C4 119.8(2) . . ? C6 C5 H5A 120.1 . . ? C4 C5 H5A 120.1 . . ? C5 C6 C7 119.3(2) . . ? C5 C6 H6A 120.3 . . ? C7 C6 H6A 120.3 . . ? C8 C7 C6 117.2(2) . . ? C8 C7 C15 118.5(2) . . ? C6 C7 C15 124.3(2) . . ? N2 C8 C7 123.0(2) . . ? N2 C8 C13 116.76(19) . . ? C7 C8 C13 120.2(2) . . ? N3 C9 C10 122.4(2) . . ? N3 C9 H9A 118.8 . . ? C10 C9 H9A 118.8 . . ? C11 C10 C9 119.6(2) . . ? C11 C10 H10A 120.2 . . ? C9 C10 H10A 120.2 . . ? C10 C11 C12 119.7(2) . . ? C10 C11 H11A 120.2 . . ? C12 C11 H11A 120.2 . . ? C11 C12 C13 116.9(2) . . ? C11 C12 C14 125.0(2) . . ? C13 C12 C14 118.1(2) . . ? N3 C13 C12 123.1(2) . . ? N3 C13 C8 116.52(19) . . ? C12 C13 C8 120.4(2) . . ? C14 C15 C7 121.3(2) . . ? C14 C15 H15A 119.4 . . ? C7 C15 H15A 119.4 . . ? C15 C14 C12 121.5(2) . . ? C15 C14 H14A 119.3 . . ? C12 C14 H14A 119.3 . . ? 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 Cu O1 C1 3.85(16) . . . . ? N3 Cu O1 C1 178.36(16) . . . . ? N2 Cu O1 C1 106.2(2) . . . . ? O4 Cu O1 C1 -89.21(17) . . . . ? O7 Cu O1 C1 -42.05(17) 2_657 . . . ? O2 Cu O1 C1 -112.71(17) 2_666 . . . ? O1 Cu N1 C2 -5.60(16) . . . . ? N3 Cu N1 C2 -51.3(6) . . . . ? N2 Cu N1 C2 -166.80(16) . . . . ? O4 Cu N1 C2 94.40(17) . . . . ? O7 Cu N1 C2 116.20(18) 2_657 . . . ? O2 Cu N1 C2 52.04(17) 2_666 . . . ? O1 Cu N1 O3 179.69(18) . . . . ? N3 Cu N1 O3 134.0(5) . . . . ? N2 Cu N1 O3 18.49(18) . . . . ? O4 Cu N1 O3 -80.31(18) . . . . ? O7 Cu N1 O3 -58.51(16) 2_657 . . . ? O2 Cu N1 O3 -122.66(16) 2_666 . . . ? O1 Cu N2 C4 -108.4(3) . . . . ? N1 Cu N2 C4 -9.2(2) . . . . ? N3 Cu N2 C4 177.8(2) . . . . ? O4 Cu N2 C4 86.9(2) . . . . ? O7 Cu N2 C4 41.8(2) 2_657 . . . ? O2 Cu N2 C4 119.3(2) 2_666 . . . ? O1 Cu N2 C8 70.5(3) . . . . ? N1 Cu N2 C8 169.72(14) . . . . ? N3 Cu N2 C8 -3.29(14) . . . . ? O4 Cu N2 C8 -94.19(15) . . . . ? O7 Cu N2 C8 -139.27(14) 2_657 . . . ? O2 Cu N2 C8 -61.75(16) 2_666 . . . ? O1 Cu N3 C9 20.8(2) . . . . ? N1 Cu N3 C9 66.0(6) . . . . ? N2 Cu N3 C9 -177.3(2) . . . . ? O4 Cu N3 C9 -79.8(2) . . . . ? O7 Cu N3 C9 -100.0(2) 2_657 . . . ? O2 Cu N3 C9 -39.82(19) 2_666 . . . ? O1 Cu N3 C13 -158.78(15) . . . . ? N1 Cu N3 C13 -113.5(5) . . . . ? N2 Cu N3 C13 3.11(15) . . . . ? O4 Cu N3 C13 100.64(15) . . . . ? O7 Cu N3 C13 80.46(17) 2_657 . . . ? O2 Cu N3 C13 140.60(16) 2_666 . . . ? Cu O1 C1 O2 178.54(19) . . . . ? Cu O1 C1 C2 -1.7(3) . . . . ? O3 N1 C2 C3 2.2(3) . . . . ? Cu N1 C2 C3 -172.84(19) . . . . ? O3 N1 C2 C1 -178.92(18) . . . . ? Cu N1 C2 C1 6.1(2) . . . . ? O2 C1 C2 N1 176.8(2) . . . . ? O1 C1 C2 N1 -2.9(3) . . . . ? O2 C1 C2 C3 -4.3(4) . . . . ? O1 C1 C2 C3 176.0(2) . . . . ? C8 N2 C4 C5 -0.6(4) . . . . ? Cu N2 C4 C5 178.27(19) . . . . ? N2 C4 C5 C6 0.0(4) . . . . ? C4 C5 C6 C7 0.7(4) . . . . ? C5 C6 C7 C8 -0.8(3) . . . . ? C5 C6 C7 C15 178.3(2) . . . . ? C4 N2 C8 C7 0.5(3) . . . . ? Cu N2 C8 C7 -178.58(16) . . . . ? C4 N2 C8 C13 -177.97(19) . . . . ? Cu N2 C8 C13 3.0(2) . . . . ? C6 C7 C8 N2 0.2(3) . . . . ? C15 C7 C8 N2 -178.9(2) . . . . ? C6 C7 C8 C13 178.61(19) . . . . ? C15 C7 C8 C13 -0.6(3) . . . . ? C13 N3 C9 C10 -0.2(3) . . . . ? Cu N3 C9 C10 -179.74(19) . . . . ? N3 C9 C10 C11 1.3(4) . . . . ? C9 C10 C11 C12 -1.2(4) . . . . ? C10 C11 C12 C13 0.1(4) . . . . ? C10 C11 C12 C14 -178.2(3) . . . . ? C9 N3 C13 C12 -1.0(3) . . . . ? Cu N3 C13 C12 178.66(16) . . . . ? C9 N3 C13 C8 177.96(19) . . . . ? Cu N3 C13 C8 -2.4(2) . . . . ? C11 C12 C13 N3 1.0(3) . . . . ? C14 C12 C13 N3 179.5(2) . . . . ? C11 C12 C13 C8 -177.9(2) . . . . ? C14 C12 C13 C8 0.6(3) . . . . ? N2 C8 C13 N3 -0.4(3) . . . . ? C7 C8 C13 N3 -178.91(19) . . . . ? N2 C8 C13 C12 178.53(18) . . . . ? C7 C8 C13 C12 0.0(3) . . . . ? C8 C7 C15 C14 0.4(3) . . . . ? C6 C7 C15 C14 -178.7(2) . . . . ? C7 C15 C14 C12 0.2(4) . . . . ? C11 C12 C14 C15 177.6(2) . . . . ? C13 C12 C14 C15 -0.7(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 O4 H2 O2 0.80 2.04 2.776(3) 153.4 2_666 O4 H1 O7 0.82 2.05 2.858(3) 168.1 2_657 O5 H4 O1 0.94 1.92 2.852(3) 169.1 2_666 O5 H3 O2 0.87 1.93 2.798(3) 179.2 1_455 O6 H5 O3 0.88 1.90 2.771(3) 169.4 2_757 O6 H6 O6 0.87 1.82 2.667(5) 165.6 2_757 O7 H7 O3 0.96 1.79 2.734(3) 163.6 2_657 O7 H8 O6 1.09 1.62 2.704(4) 171.0 . O8 H9 O5 0.88 2.00 2.790(3) 149.8 2_657 O8 H10' O7 0.80 1.93 2.731(4) 176.9 . O8 H10 O8 0.88 1.87 2.730(5) 166.5 2_658 _diffrn_measured_fraction_theta_max 0.876 _diffrn_reflns_theta_full 28.76 _diffrn_measured_fraction_theta_full 0.876 _refine_diff_density_max 0.648 _refine_diff_density_min -0.552 _refine_diff_density_rms 0.067