# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_p-144 _audit_creation_method SHELXL-97 _chemical_name_systematic tetra-acetato-coprate(II) _chemical_name_common ? _chemical_formula_moiety 'C8 H12 Cu O8, C12 H20 N4' _chemical_formula_sum 'C20 H32 Cu N4 O8' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour blue _diffrn_ambient_temperature 150(2) _chemical_formula_weight 520.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.289(4) _cell_length_b 9.297(4) _cell_length_c 16.608(8) _cell_angle_alpha 78.487(7) _cell_angle_beta 75.633(7) _cell_angle_gamma 89.994(7) _cell_volume 1213.2(10) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 729 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 16.25 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 546 _exptl_absorpt_coefficient_mu 0.951 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8326 _exptl_absorpt_correction_T_max 0.9109 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11361 _diffrn_reflns_av_R_equivalents 0.1250 _diffrn_reflns_av_sigmaI/netI 0.1812 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4744 _reflns_number_gt 2568 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0718P)^2^+6.0663P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4744 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1758 _refine_ls_R_factor_gt 0.0931 _refine_ls_wR_factor_ref 0.2396 _refine_ls_wR_factor_gt 0.2033 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.54622(13) 0.70140(12) 0.71963(7) 0.0221(3) Uani 1 1 d . . . O5 O 0.3387(7) 0.6984(6) 0.8097(4) 0.0247(14) Uani 1 1 d . . . O7 O 0.7579(7) 0.7262(7) 0.6358(4) 0.0280(15) Uani 1 1 d . . . O1 O 0.6656(7) 0.6647(7) 0.8094(4) 0.0297(15) Uani 1 1 d . . . O3 O 0.4247(7) 0.7364(6) 0.6305(4) 0.0293(15) Uani 1 1 d . . . O4 O 0.4536(8) 0.4947(7) 0.6418(4) 0.0323(16) Uani 1 1 d . . . N1 N -0.0366(8) 0.4027(7) 0.6855(4) 0.0195(16) Uani 1 1 d . . . N3 N 0.1712(8) 0.0748(8) 0.6767(4) 0.0208(16) Uani 1 1 d . . . N2 N 0.1357(8) 0.3577(7) 0.7665(4) 0.0199(16) Uani 1 1 d . . . N4 N -0.0867(8) 0.0489(8) 0.7495(5) 0.0238(17) Uani 1 1 d . . . C9 C 0.0488(10) 0.2981(9) 0.7207(5) 0.0198(19) Uani 1 1 d . . . C17 C -0.0404(10) -0.0831(10) 0.7309(6) 0.026(2) Uani 1 1 d . . . H17 H -0.1092 -0.1711 0.7469 0.031 Uiso 1 1 calc R . . C16 C 0.1173(11) -0.0679(9) 0.6865(6) 0.026(2) Uani 1 1 d . . . H16 H 0.1817 -0.1431 0.6653 0.032 Uiso 1 1 calc R . . C10 C -0.0050(11) 0.5313(9) 0.7088(6) 0.026(2) Uani 1 1 d . . . H10 H -0.0506 0.6231 0.6928 0.031 Uiso 1 1 calc R . . C14 C -0.1473(11) 0.3850(10) 0.6315(6) 0.029(2) Uani 1 1 d . . . H14A H -0.1159 0.3001 0.6053 0.044 Uiso 1 1 calc R . . H14B H -0.1374 0.4737 0.5870 0.044 Uiso 1 1 calc R . . H14C H -0.2628 0.3692 0.6660 0.044 Uiso 1 1 calc R . . C15 C 0.0427(10) 0.1452(9) 0.7160(5) 0.0211(19) Uani 1 1 d . . . C11 C 0.1029(10) 0.5037(9) 0.7586(6) 0.025(2) Uani 1 1 d . . . H11 H 0.1477 0.5727 0.7834 0.030 Uiso 1 1 calc R . . C18 C -0.2527(11) 0.0797(10) 0.8001(7) 0.039(3) Uani 1 1 d . . . H18A H -0.3407 0.0476 0.7757 0.047 Uiso 1 1 calc R . . H18B H -0.2593 0.1867 0.7975 0.047 Uiso 1 1 calc R . . C20 C 0.3357(10) 0.1408(10) 0.6306(6) 0.027(2) Uani 1 1 d . . . H20A H 0.3537 0.1397 0.5702 0.041 Uiso 1 1 calc R . . H20B H 0.4209 0.0846 0.6530 0.041 Uiso 1 1 calc R . . H20C H 0.3435 0.2425 0.6377 0.041 Uiso 1 1 calc R . . C12 C 0.2567(11) 0.2843(10) 0.8118(5) 0.026(2) Uani 1 1 d . . . H12A H 0.3685 0.3342 0.7865 0.032 Uiso 1 1 calc R . . H12B H 0.2642 0.1808 0.8053 0.032 Uiso 1 1 calc R . . C13 C 0.2029(14) 0.2892(13) 0.9050(6) 0.052(3) Uani 1 1 d . . . H13A H 0.1992 0.3917 0.9115 0.078 Uiso 1 1 calc R . . H13B H 0.2827 0.2387 0.9342 0.078 Uiso 1 1 calc R . . H13C H 0.0919 0.2402 0.9299 0.078 Uiso 1 1 calc R . . C19 C -0.2819(16) 0.0003(16) 0.8912(7) 0.069(4) Uani 1 1 d . . . H19A H -0.2877 -0.1060 0.8943 0.104 Uiso 1 1 calc R . . H19B H -0.3871 0.0293 0.9246 0.104 Uiso 1 1 calc R . . H19C H -0.1899 0.0260 0.9140 0.104 Uiso 1 1 calc R . . C3 C 0.4069(11) 0.6125(10) 0.6075(5) 0.024(2) Uani 1 1 d . . . C4 C 0.3243(11) 0.6186(11) 0.5361(6) 0.032(2) Uani 1 1 d . . . H4A H 0.4068 0.6514 0.4817 0.048 Uiso 1 1 calc R . . H4B H 0.2350 0.6878 0.5415 0.048 Uiso 1 1 calc R . . H4C H 0.2772 0.5207 0.5386 0.048 Uiso 1 1 calc R . . C1 C 0.6628(11) 0.5309(11) 0.8476(6) 0.029(2) Uani 1 1 d . . . C2 C 0.7326(14) 0.5090(13) 0.9256(6) 0.049(3) Uani 1 1 d . . . H2A H 0.6907 0.4137 0.9626 0.074 Uiso 1 1 calc R . . H2B H 0.6974 0.5876 0.9566 0.074 Uiso 1 1 calc R . . H2C H 0.8547 0.5117 0.9077 0.074 Uiso 1 1 calc R . . O2 O 0.6133(8) 0.4243(7) 0.8255(4) 0.0416(18) Uani 1 1 d . . . O6 O 0.4106(8) 0.9363(7) 0.7896(4) 0.0336(16) Uani 1 1 d . . . C5 C 0.3184(10) 0.8226(10) 0.8287(5) 0.023(2) Uani 1 1 d . . . C6 C 0.1801(13) 0.8347(12) 0.9030(6) 0.044(3) Uani 1 1 d . . . H6A H 0.1103 0.7432 0.9217 0.065 Uiso 1 1 calc R . . H6B H 0.1125 0.9167 0.8868 0.065 Uiso 1 1 calc R . . H6C H 0.2261 0.8521 0.9493 0.065 Uiso 1 1 calc R . . C8 C 0.7490(12) 0.9731(10) 0.5631(6) 0.036(2) Uani 1 1 d . . . H8A H 0.8464 1.0421 0.5388 0.055 Uiso 1 1 calc R . . H8B H 0.6965 0.9846 0.6211 0.055 Uiso 1 1 calc R . . H8C H 0.6688 0.9936 0.5282 0.055 Uiso 1 1 calc R . . O8 O 0.8968(9) 0.7871(8) 0.4998(5) 0.0477(19) Uani 1 1 d . . . C7 C 0.8032(12) 0.8180(11) 0.5650(7) 0.033(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0167(6) 0.0232(6) 0.0292(7) -0.0073(5) -0.0091(5) 0.0022(4) O5 0.023(3) 0.026(4) 0.026(4) -0.006(3) -0.008(3) -0.004(3) O7 0.016(3) 0.036(4) 0.029(4) -0.002(3) -0.004(3) 0.005(3) O1 0.020(3) 0.036(4) 0.038(4) -0.014(3) -0.011(3) 0.000(3) O3 0.033(4) 0.023(4) 0.036(4) -0.009(3) -0.014(3) 0.011(3) O4 0.039(4) 0.028(4) 0.034(4) -0.009(3) -0.015(3) 0.011(3) N1 0.013(3) 0.025(4) 0.023(4) -0.010(3) -0.005(3) 0.003(3) N3 0.020(4) 0.026(4) 0.023(4) -0.010(3) -0.015(3) 0.010(3) N2 0.015(4) 0.023(4) 0.027(4) -0.009(3) -0.010(3) 0.003(3) N4 0.012(4) 0.028(4) 0.038(5) -0.015(4) -0.011(3) 0.003(3) C9 0.010(4) 0.022(5) 0.029(5) -0.007(4) -0.005(4) 0.005(3) C17 0.017(5) 0.022(5) 0.041(6) -0.008(4) -0.010(4) -0.001(4) C16 0.031(5) 0.021(5) 0.034(6) -0.011(4) -0.018(4) 0.007(4) C10 0.031(5) 0.012(5) 0.035(6) -0.007(4) -0.009(4) 0.005(4) C14 0.032(5) 0.035(6) 0.027(5) -0.010(4) -0.015(4) 0.003(4) C15 0.017(4) 0.026(5) 0.023(5) -0.008(4) -0.008(4) 0.012(4) C11 0.016(4) 0.025(5) 0.037(6) -0.017(4) -0.003(4) -0.005(4) C18 0.022(5) 0.023(5) 0.061(8) -0.012(5) 0.012(5) -0.009(4) C20 0.021(5) 0.036(6) 0.028(5) -0.010(4) -0.008(4) 0.015(4) C12 0.027(5) 0.028(5) 0.028(5) -0.007(4) -0.013(4) -0.004(4) C13 0.057(7) 0.076(9) 0.030(6) -0.021(6) -0.015(5) 0.024(6) C19 0.061(8) 0.108(12) 0.036(7) -0.028(7) 0.003(6) 0.021(8) C3 0.029(5) 0.024(5) 0.020(5) -0.011(4) -0.001(4) 0.005(4) C4 0.022(5) 0.047(6) 0.029(5) -0.012(5) -0.010(4) 0.003(4) C1 0.022(5) 0.031(6) 0.037(6) -0.011(5) -0.008(4) 0.007(4) C2 0.052(7) 0.076(9) 0.024(6) -0.004(6) -0.021(5) 0.003(6) O2 0.035(4) 0.035(4) 0.060(5) -0.008(4) -0.022(4) 0.002(3) O6 0.038(4) 0.031(4) 0.033(4) -0.002(3) -0.016(3) -0.006(3) C5 0.023(5) 0.023(5) 0.028(5) -0.010(4) -0.015(4) 0.003(4) C6 0.054(7) 0.044(7) 0.037(6) -0.017(5) -0.013(5) 0.019(5) C8 0.032(6) 0.026(6) 0.049(7) -0.003(5) -0.011(5) 0.010(4) O8 0.048(5) 0.052(5) 0.040(5) -0.014(4) -0.002(4) 0.014(4) C7 0.030(5) 0.035(6) 0.038(6) -0.005(5) -0.017(5) 0.004(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O7 1.931(6) . ? Cu1 O1 1.961(6) . ? Cu1 O3 1.964(6) . ? Cu1 O5 1.976(6) . ? O5 C5 1.258(10) . ? O7 C7 1.278(11) . ? O1 C1 1.276(11) . ? O3 C3 1.304(10) . ? O4 C3 1.238(10) . ? N1 C9 1.328(10) . ? N1 C10 1.371(10) . ? N1 C14 1.464(10) . ? N3 C15 1.346(10) . ? N3 C16 1.366(10) . ? N3 C20 1.455(11) . ? N2 C9 1.358(10) . ? N2 C11 1.371(10) . ? N2 C12 1.486(10) . ? N4 C15 1.329(11) . ? N4 C17 1.357(10) . ? N4 C18 1.484(11) . ? C9 C15 1.441(11) . ? C17 C16 1.324(12) . ? C17 H17 0.9500 . ? C16 H16 0.9500 . ? C10 C11 1.353(11) . ? C10 H10 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C11 H11 0.9500 . ? C18 C19 1.505(14) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C12 C13 1.511(12) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C3 C4 1.501(11) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C1 O2 1.228(10) . ? C1 C2 1.523(12) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? O6 C5 1.266(10) . ? C5 C6 1.484(13) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C8 C7 1.508(13) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? O8 C7 1.251(11) . ? 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 O7 Cu1 O1 89.2(3) . . ? O7 Cu1 O3 91.3(3) . . ? O1 Cu1 O3 179.3(3) . . ? O7 Cu1 O5 172.8(3) . . ? O1 Cu1 O5 87.7(2) . . ? O3 Cu1 O5 91.9(2) . . ? C5 O5 Cu1 110.6(6) . . ? C7 O7 Cu1 129.2(6) . . ? C1 O1 Cu1 115.7(6) . . ? C3 O3 Cu1 108.3(5) . . ? C9 N1 C10 108.6(7) . . ? C9 N1 C14 126.2(7) . . ? C10 N1 C14 125.2(7) . . ? C15 N3 C16 107.5(7) . . ? C15 N3 C20 125.8(7) . . ? C16 N3 C20 126.6(7) . . ? C9 N2 C11 107.9(7) . . ? C9 N2 C12 127.2(7) . . ? C11 N2 C12 124.7(6) . . ? C15 N4 C17 108.4(7) . . ? C15 N4 C18 125.9(7) . . ? C17 N4 C18 125.7(7) . . ? N1 C9 N2 108.4(7) . . ? N1 C9 C15 126.2(7) . . ? N2 C9 C15 125.2(7) . . ? C16 C17 N4 108.1(8) . . ? C16 C17 H17 126.0 . . ? N4 C17 H17 126.0 . . ? C17 C16 N3 107.9(8) . . ? C17 C16 H16 126.0 . . ? N3 C16 H16 126.0 . . ? C11 C10 N1 107.7(7) . . ? C11 C10 H10 126.2 . . ? N1 C10 H10 126.2 . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N4 C15 N3 108.1(7) . . ? N4 C15 C9 127.0(7) . . ? N3 C15 C9 124.9(7) . . ? C10 C11 N2 107.4(7) . . ? C10 C11 H11 126.3 . . ? N2 C11 H11 126.3 . . ? N4 C18 C19 110.7(9) . . ? N4 C18 H18A 109.5 . . ? C19 C18 H18A 109.5 . . ? N4 C18 H18B 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 108.1 . . ? N3 C20 H20A 109.5 . . ? N3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N2 C12 C13 110.5(8) . . ? N2 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? N2 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O4 C3 O3 123.1(8) . . ? O4 C3 C4 120.7(8) . . ? O3 C3 C4 116.2(8) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C1 O1 125.6(9) . . ? O2 C1 C2 120.1(9) . . ? O1 C1 C2 114.3(9) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O5 C5 O6 124.0(8) . . ? O5 C5 C6 117.5(8) . . ? O6 C5 C6 118.4(8) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O8 C7 O7 123.2(9) . . ? O8 C7 C8 119.4(9) . . ? O7 C7 C8 117.3(9) . . ? 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 O7 Cu1 O5 C5 20(2) . . . . ? O1 Cu1 O5 C5 84.7(5) . . . . ? O3 Cu1 O5 C5 -95.8(5) . . . . ? O1 Cu1 O7 C7 -141.1(8) . . . . ? O3 Cu1 O7 C7 39.3(8) . . . . ? O5 Cu1 O7 C7 -77(2) . . . . ? O7 Cu1 O1 C1 -104.8(6) . . . . ? O3 Cu1 O1 C1 37(25) . . . . ? O5 Cu1 O1 C1 81.8(6) . . . . ? O7 Cu1 O3 C3 84.9(6) . . . . ? O1 Cu1 O3 C3 -57(25) . . . . ? O5 Cu1 O3 C3 -101.6(6) . . . . ? C10 N1 C9 N2 -0.1(9) . . . . ? C14 N1 C9 N2 -179.6(7) . . . . ? C10 N1 C9 C15 176.2(8) . . . . ? C14 N1 C9 C15 -3.3(13) . . . . ? C11 N2 C9 N1 -0.4(9) . . . . ? C12 N2 C9 N1 -175.6(7) . . . . ? C11 N2 C9 C15 -176.7(8) . . . . ? C12 N2 C9 C15 8.1(13) . . . . ? C15 N4 C17 C16 0.3(10) . . . . ? C18 N4 C17 C16 -178.5(8) . . . . ? N4 C17 C16 N3 -0.2(10) . . . . ? C15 N3 C16 C17 0.0(9) . . . . ? C20 N3 C16 C17 -178.7(7) . . . . ? C9 N1 C10 C11 0.5(10) . . . . ? C14 N1 C10 C11 -180.0(8) . . . . ? C17 N4 C15 N3 -0.3(9) . . . . ? C18 N4 C15 N3 178.5(8) . . . . ? C17 N4 C15 C9 -179.8(8) . . . . ? C18 N4 C15 C9 -0.9(14) . . . . ? C16 N3 C15 N4 0.2(9) . . . . ? C20 N3 C15 N4 178.9(7) . . . . ? C16 N3 C15 C9 179.7(7) . . . . ? C20 N3 C15 C9 -1.6(12) . . . . ? N1 C9 C15 N4 -66.0(12) . . . . ? N2 C9 C15 N4 109.7(10) . . . . ? N1 C9 C15 N3 114.6(9) . . . . ? N2 C9 C15 N3 -69.7(12) . . . . ? N1 C10 C11 N2 -0.7(10) . . . . ? C9 N2 C11 C10 0.7(10) . . . . ? C12 N2 C11 C10 176.0(8) . . . . ? C15 N4 C18 C19 -111.6(10) . . . . ? C17 N4 C18 C19 67.1(12) . . . . ? C9 N2 C12 C13 -122.3(10) . . . . ? C11 N2 C12 C13 63.2(11) . . . . ? Cu1 O3 C3 O4 3.5(10) . . . . ? Cu1 O3 C3 C4 -176.9(6) . . . . ? Cu1 O1 C1 O2 10.7(12) . . . . ? Cu1 O1 C1 C2 -170.9(6) . . . . ? Cu1 O5 C5 O6 6.2(10) . . . . ? Cu1 O5 C5 C6 -172.3(6) . . . . ? Cu1 O7 C7 O8 -143.4(7) . . . . ? Cu1 O7 C7 C8 40.8(11) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.811 _refine_diff_density_min -0.735 _refine_diff_density_rms 0.137 _database_code_depnum_ccdc_archive 'CCDC 949829' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic tetra-mu-acetato-bis-1-ethyl-3-methyl-1H-imidazol-2(3H)-one-dicopper(II) _chemical_name_common ? _chemical_formula_moiety 'C20 H32 Cu2 N4 O10' _chemical_formula_sum 'C20 H32 Cu2 N4 O10' _chemical_melting_point ? _exptl_crystal_description blue _exptl_crystal_colour prism _diffrn_ambient_temperature 150(2) _chemical_formula_weight 615.58 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.5500(6) _cell_length_b 8.3061(6) _cell_length_c 17.5899(12) _cell_angle_alpha 90.00 _cell_angle_beta 93.800(2) _cell_angle_gamma 90.00 _cell_volume 1246.44(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3504 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 27.46 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 636 _exptl_absorpt_coefficient_mu 1.767 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6384 _exptl_absorpt_correction_T_max 0.6972 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9202 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2455 _reflns_number_gt 2182 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2455 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0347 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 0.856 _refine_ls_restrained_S_all 0.856 _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 0.49413(3) 0.45662(3) 0.071849(15) 0.01278(14) Uani 1 1 d . . . O4 O 0.7056(2) 0.5529(2) 0.07966(10) 0.0207(4) Uani 1 1 d . . . O1 O 0.3964(2) 0.6699(2) 0.07952(9) 0.0210(4) Uani 1 1 d . . . O2 O 0.2861(2) 0.3678(2) 0.04159(9) 0.0201(4) Uani 1 1 d . . . O3 O 0.5892(2) 0.2530(2) 0.04181(9) 0.0198(4) Uani 1 1 d . . . O5 O 0.4934(2) 0.4133(2) 0.19216(9) 0.0182(4) Uani 1 1 d . . . C1 C 0.3731(3) 0.7694(3) 0.02586(13) 0.0161(5) Uani 1 1 d . . . C3 C 0.7717(3) 0.6183(3) 0.02594(13) 0.0170(5) Uani 1 1 d . . . C2 C 0.2940(3) 0.9268(3) 0.04285(15) 0.0224(6) Uani 1 1 d . . . H2A H 0.2371 0.9151 0.0878 0.034 Uiso 1 1 calc R . . H2B H 0.2228 0.9558 0.0006 0.034 Uiso 1 1 calc R . . H2C H 0.3718 1.0094 0.0510 0.034 Uiso 1 1 calc R . . C4 C 0.9321(3) 0.6888(4) 0.04454(16) 0.0274(6) Uani 1 1 d . . . H4A H 0.9250 0.7734 0.0813 0.041 Uiso 1 1 calc R . . H4B H 0.9723 0.7315 -0.0010 0.041 Uiso 1 1 calc R . . H4C H 1.0012 0.6063 0.0651 0.041 Uiso 1 1 calc R . . N2 N 0.3747(2) 0.5926(3) 0.27328(11) 0.0185(4) Uani 1 1 d . . . N1 N 0.6295(2) 0.5740(3) 0.28431(11) 0.0175(4) Uani 1 1 d . . . C8 C 0.7898(3) 0.5263(3) 0.27189(16) 0.0233(6) Uani 1 1 d . . . H8A H 0.8570 0.6204 0.2759 0.028 Uiso 1 1 calc R . . H8B H 0.7936 0.4832 0.2208 0.028 Uiso 1 1 calc R . . C6 C 0.5844(3) 0.6814(3) 0.33962(14) 0.0220(6) Uani 1 1 d . . . H6 H 0.6510 0.7351 0.3751 0.026 Uiso 1 1 calc R . . C11 C 0.2141(3) 0.5747(4) 0.24256(17) 0.0305(7) Uani 1 1 d . . . H11A H 0.2093 0.5907 0.1884 0.046 Uiso 1 1 calc R . . H11B H 0.1493 0.6532 0.2654 0.046 Uiso 1 1 calc R . . H11C H 0.1774 0.4686 0.2535 0.046 Uiso 1 1 calc R . . C9 C 0.8501(3) 0.4023(4) 0.32834(15) 0.0275(6) Uani 1 1 d . . . H9A H 0.8550 0.4476 0.3787 0.041 Uiso 1 1 calc R . . H9B H 0.9530 0.3688 0.3163 0.041 Uiso 1 1 calc R . . H9C H 0.7810 0.3111 0.3263 0.041 Uiso 1 1 calc R . . C5 C 0.4998(3) 0.5177(3) 0.24360(14) 0.0149(5) Uani 1 1 d . . . C7 C 0.4286(3) 0.6935(3) 0.33266(13) 0.0207(5) Uani 1 1 d . . . H7 H 0.3670 0.7576 0.3621 0.025 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0143(2) 0.0128(2) 0.0113(2) 0.00020(10) 0.00081(13) -0.00111(10) O4 0.0174(9) 0.0289(11) 0.0156(9) 0.0002(7) 0.0002(7) -0.0067(7) O1 0.0289(10) 0.0155(9) 0.0188(8) 0.0006(7) 0.0022(7) 0.0036(7) O2 0.0181(9) 0.0249(10) 0.0175(9) 0.0019(7) 0.0011(7) -0.0067(7) O3 0.0245(10) 0.0167(9) 0.0181(9) 0.0004(7) 0.0018(7) 0.0044(7) O5 0.0259(10) 0.0163(9) 0.0126(8) 0.0006(7) 0.0025(7) -0.0003(7) C1 0.0141(12) 0.0135(12) 0.0204(12) -0.0028(10) -0.0018(9) -0.0030(9) C3 0.0126(12) 0.0172(13) 0.0216(12) -0.0041(10) 0.0035(9) 0.0002(9) C2 0.0231(14) 0.0203(13) 0.0237(14) -0.0022(10) 0.0012(11) 0.0036(11) C4 0.0164(13) 0.0370(16) 0.0287(14) -0.0005(12) 0.0011(11) -0.0068(12) N2 0.0162(11) 0.0199(11) 0.0194(10) -0.0023(9) 0.0021(8) -0.0008(9) N1 0.0168(11) 0.0203(11) 0.0155(10) 0.0008(8) 0.0014(8) -0.0001(8) C8 0.0157(14) 0.0300(16) 0.0241(14) 0.0067(11) 0.0021(10) 0.0017(11) C6 0.0272(14) 0.0239(14) 0.0146(11) -0.0034(10) -0.0009(10) -0.0049(11) C11 0.0159(14) 0.0399(17) 0.0358(16) -0.0048(13) 0.0021(12) -0.0019(12) C9 0.0272(16) 0.0302(15) 0.0248(14) 0.0026(12) -0.0002(11) 0.0085(12) C5 0.0166(13) 0.0155(12) 0.0130(11) 0.0030(9) 0.0036(9) -0.0003(9) C7 0.0264(14) 0.0212(13) 0.0152(11) -0.0021(10) 0.0061(10) 0.0002(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 Cu1 O3 1.9642(17) . ? Cu1 O2 1.9664(17) . ? Cu1 O1 1.9670(18) . ? Cu1 O4 1.9737(18) . ? Cu1 O5 2.1469(16) . ? Cu1 Cu1 2.6366(5) 3_665 ? O4 C3 1.256(3) . ? O1 C1 1.260(3) . ? O2 C3 1.261(3) 3_665 ? O3 C1 1.267(3) 3_665 ? O5 C5 1.251(3) . ? C1 O3 1.267(3) 3_665 ? C1 C2 1.511(3) . ? C3 O2 1.261(3) 3_665 ? C3 C4 1.507(3) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? N2 C5 1.370(3) . ? N2 C7 1.394(3) . ? N2 C11 1.449(3) . ? N1 C5 1.363(3) . ? N1 C6 1.393(3) . ? N1 C8 1.457(3) . ? C8 C9 1.498(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C6 C7 1.334(4) . ? C6 H6 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C7 H7 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 O3 Cu1 O2 89.27(8) . . ? O3 Cu1 O1 168.30(7) . . ? O2 Cu1 O1 88.58(8) . . ? O3 Cu1 O4 88.52(7) . . ? O2 Cu1 O4 168.27(7) . . ? O1 Cu1 O4 91.26(8) . . ? O3 Cu1 O5 98.59(7) . . ? O2 Cu1 O5 98.18(7) . . ? O1 Cu1 O5 93.10(7) . . ? O4 Cu1 O5 93.55(7) . . ? O3 Cu1 Cu1 86.26(5) . 3_665 ? O2 Cu1 Cu1 86.23(5) . 3_665 ? O1 Cu1 Cu1 82.13(5) . 3_665 ? O4 Cu1 Cu1 82.13(5) . 3_665 ? O5 Cu1 Cu1 173.45(5) . 3_665 ? C3 O4 Cu1 125.36(16) . . ? C1 O1 Cu1 125.86(15) . . ? C3 O2 Cu1 120.79(15) 3_665 . ? C1 O3 Cu1 120.95(15) 3_665 . ? C5 O5 Cu1 126.44(16) . . ? O1 C1 O3 124.7(2) . 3_665 ? O1 C1 C2 118.0(2) . . ? O3 C1 C2 117.2(2) 3_665 . ? O4 C3 O2 125.4(2) . 3_665 ? O4 C3 C4 116.9(2) . . ? O2 C3 C4 117.6(2) 3_665 . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C5 N2 C7 109.3(2) . . ? C5 N2 C11 123.8(2) . . ? C7 N2 C11 126.8(2) . . ? C5 N1 C6 109.5(2) . . ? C5 N1 C8 124.7(2) . . ? C6 N1 C8 125.8(2) . . ? N1 C8 C9 111.9(2) . . ? N1 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? N1 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C7 C6 N1 107.8(2) . . ? C7 C6 H6 126.1 . . ? N1 C6 H6 126.1 . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C5 N1 127.8(2) . . ? O5 C5 N2 126.3(2) . . ? N1 C5 N2 105.8(2) . . ? C6 C7 N2 107.6(2) . . ? C6 C7 H7 126.2 . . ? N2 C7 H7 126.2 . . ? 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 O3 Cu1 O4 C3 87.9(2) . . . . ? O2 Cu1 O4 C3 8.7(5) . . . . ? O1 Cu1 O4 C3 -80.4(2) . . . . ? O5 Cu1 O4 C3 -173.6(2) . . . . ? Cu1 Cu1 O4 C3 1.49(19) 3_665 . . . ? O3 Cu1 O1 C1 -7.8(5) . . . . ? O2 Cu1 O1 C1 -87.3(2) . . . . ? O4 Cu1 O1 C1 80.9(2) . . . . ? O5 Cu1 O1 C1 174.5(2) . . . . ? Cu1 Cu1 O1 C1 -0.95(19) 3_665 . . . ? O3 Cu1 O2 C3 -88.31(19) . . . 3_665 ? O1 Cu1 O2 C3 80.19(19) . . . 3_665 ? O4 Cu1 O2 C3 -9.2(5) . . . 3_665 ? O5 Cu1 O2 C3 173.11(18) . . . 3_665 ? Cu1 Cu1 O2 C3 -2.01(18) 3_665 . . 3_665 ? O2 Cu1 O3 C1 88.64(18) . . . 3_665 ? O1 Cu1 O3 C1 9.2(5) . . . 3_665 ? O4 Cu1 O3 C1 -79.84(18) . . . 3_665 ? O5 Cu1 O3 C1 -173.20(17) . . . 3_665 ? Cu1 Cu1 O3 C1 2.37(17) 3_665 . . 3_665 ? O3 Cu1 O5 C5 152.1(2) . . . . ? O2 Cu1 O5 C5 -117.4(2) . . . . ? O1 Cu1 O5 C5 -28.4(2) . . . . ? O4 Cu1 O5 C5 63.1(2) . . . . ? Cu1 Cu1 O5 C5 14.6(6) 3_665 . . . ? Cu1 O1 C1 O3 -0.6(3) . . . 3_665 ? Cu1 O1 C1 C2 179.19(16) . . . . ? Cu1 O4 C3 O2 -0.4(4) . . . 3_665 ? Cu1 O4 C3 C4 178.30(17) . . . . ? C5 N1 C8 C9 -100.0(3) . . . . ? C6 N1 C8 C9 79.1(3) . . . . ? C5 N1 C6 C7 -0.9(3) . . . . ? C8 N1 C6 C7 179.9(2) . . . . ? Cu1 O5 C5 N1 -93.7(3) . . . . ? Cu1 O5 C5 N2 90.1(3) . . . . ? C6 N1 C5 O5 -175.9(2) . . . . ? C8 N1 C5 O5 3.3(4) . . . . ? C6 N1 C5 N2 0.9(3) . . . . ? C8 N1 C5 N2 -179.9(2) . . . . ? C7 N2 C5 O5 176.3(2) . . . . ? C11 N2 C5 O5 -7.6(4) . . . . ? C7 N2 C5 N1 -0.6(3) . . . . ? C11 N2 C5 N1 175.6(2) . . . . ? N1 C6 C7 N2 0.5(3) . . . . ? C5 N2 C7 C6 0.1(3) . . . . ? C11 N2 C7 C6 -175.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.462 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 890316'