# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_comp1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; aqua-bis(4-methylpyridine)-bis(3-nitrobenzoate) copper(ii) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H22 Cu N4 O8' _chemical_formula_sum 'C26 H22 Cu N4 O8' _chemical_formula_weight 582.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.8506(1) _cell_length_b 21.8740(4) _cell_length_c 8.1508(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.0120(6) _cell_angle_gamma 90.00 _cell_volume 1363.75(5) _cell_formula_units_Z 2 _cell_measurement_temperature 295 _cell_measurement_reflns_used 16268 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 598 _exptl_absorpt_coefficient_mu 0.855 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.708 _exptl_absorpt_correction_T_max 0.752 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _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 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16268 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 30.04 _reflns_number_total 3883 _reflns_number_gt 3325 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Kappa CCD server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al.,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997); WINGX (Farrugia, 1999) ; _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^)+(0.0647P)^2^+0.2615P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.156(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3883 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1148 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 0.0000 0.0000 0.0000 0.03762(13) Uani 1 2 d S . . N1 N -0.16572(17) -0.03408(6) 0.13129(16) 0.0423(3) Uani 1 1 d . . . O1 O -0.08036(14) -0.06319(5) -0.17554(14) 0.0433(2) Uani 1 1 d . . . O2 O 0.13813(15) -0.10425(5) 0.01185(16) 0.0501(3) Uani 1 1 d . . . N2 N 0.2899(3) -0.18756(12) -0.1978(3) 0.0882(7) Uani 1 1 d . . . O3 O 0.4029(3) -0.22138(15) -0.1225(6) 0.1748(17) Uani 1 1 d . . . O4 O 0.3166(3) -0.13774(14) -0.2510(3) 0.1142(8) Uani 1 1 d . . . C1 C -0.3262(2) -0.05327(8) 0.0539(2) 0.0474(3) Uani 1 1 d . . . C2 C -0.4445(2) -0.07557(9) 0.1407(3) 0.0567(4) Uani 1 1 d . . . C3 C -0.4000(3) -0.07909(10) 0.3138(3) 0.0628(5) Uani 1 1 d . . . C4 C -0.2320(3) -0.06112(12) 0.3928(3) 0.0709(6) Uani 1 1 d . . . C5 C -0.1208(3) -0.03874(10) 0.2990(2) 0.0606(5) Uani 1 1 d . . . C6 C -0.5278(4) -0.10311(17) 0.4121(4) 0.1040(10) Uani 1 1 d . . . H61 H -0.5423 -0.0734 0.4945 0.125 Uiso 1 1 calc R . . H62 H -0.4836 -0.1405 0.4676 0.125 Uiso 1 1 calc R . . H63 H -0.6385 -0.1107 0.3365 0.125 Uiso 1 1 calc R . . C7 C 0.01980(18) -0.10769(6) -0.11674(19) 0.0396(3) Uani 1 1 d . . . C8 C -0.02085(19) -0.16855(7) -0.2018(2) 0.0419(3) Uani 1 1 d . . . C9 C 0.1080(2) -0.20881(9) -0.2248(3) 0.0537(4) Uani 1 1 d . . . C10 C 0.0727(3) -0.26864(10) -0.2760(3) 0.0724(6) Uani 1 1 d . . . C11 C -0.0965(4) -0.28889(10) -0.3069(4) 0.0752(6) Uani 1 1 d . . . C12 C -0.2277(3) -0.25035(10) -0.2887(3) 0.0743(6) Uani 1 1 d . . . C13 C -0.1904(2) -0.19029(9) -0.2368(3) 0.0592(5) Uani 1 1 d . . . H1 H -0.355(3) -0.0511(10) -0.064(3) 0.050(5) Uiso 1 1 d . . . H2 H -0.557(3) -0.0877(11) 0.080(3) 0.068(7) Uiso 1 1 d . . . H3 H -0.355(4) -0.2686(13) -0.313(4) 0.083(8) Uiso 1 1 d . . . H4 H -0.282(3) -0.1639(12) -0.221(3) 0.075(7) Uiso 1 1 d . . . H5 H 0.005(4) -0.0238(14) 0.361(3) 0.079(7) Uiso 1 1 d . . . H6 H -0.193(3) -0.0680(12) 0.504(4) 0.079(7) Uiso 1 1 d . . . H7 H 0.163(4) -0.2967(15) -0.291(4) 0.093(9) Uiso 1 1 d . . . H8 H -0.125(3) -0.3289(13) -0.338(3) 0.084(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 Cu1 0.04464(18) 0.02987(16) 0.03737(17) -0.00257(8) 0.00715(10) -0.00559(8) N1 0.0481(6) 0.0374(6) 0.0410(6) -0.0012(5) 0.0094(5) -0.0070(5) O1 0.0508(6) 0.0349(5) 0.0426(5) -0.0044(4) 0.0071(4) -0.0030(4) O2 0.0456(6) 0.0463(6) 0.0538(7) -0.0043(5) 0.0017(5) -0.0069(4) N2 0.0541(10) 0.1010(17) 0.1163(18) -0.0411(14) 0.0336(11) 0.0001(10) O3 0.0613(12) 0.140(2) 0.300(5) -0.054(3) -0.0069(18) 0.0344(14) O4 0.0987(14) 0.150(2) 0.1115(16) -0.0272(15) 0.0611(13) -0.0567(14) C1 0.0425(7) 0.0512(8) 0.0458(8) 0.0020(6) 0.0044(6) 0.0008(6) C2 0.0416(8) 0.0651(10) 0.0614(10) 0.0043(8) 0.0075(7) -0.0042(7) C3 0.0661(11) 0.0643(11) 0.0620(11) 0.0044(9) 0.0230(9) -0.0156(8) C4 0.0836(14) 0.0846(15) 0.0439(9) 0.0021(9) 0.0129(9) -0.0336(11) C5 0.0662(11) 0.0687(11) 0.0438(8) -0.0022(8) 0.0059(7) -0.0289(9) C6 0.0935(19) 0.138(3) 0.091(2) 0.0127(19) 0.0426(16) -0.0392(18) C7 0.0412(6) 0.0353(6) 0.0438(7) -0.0044(5) 0.0129(5) -0.0075(5) C8 0.0448(7) 0.0354(6) 0.0463(7) -0.0053(5) 0.0118(6) -0.0039(5) C9 0.0519(9) 0.0509(9) 0.0606(10) -0.0118(8) 0.0175(7) 0.0025(7) C10 0.0854(14) 0.0517(10) 0.0820(15) -0.0181(10) 0.0230(11) 0.0139(10) C11 0.1000(17) 0.0390(9) 0.0885(16) -0.0210(10) 0.0254(13) -0.0120(10) C12 0.0698(12) 0.0572(11) 0.0964(17) -0.0268(11) 0.0200(11) -0.0249(9) C13 0.0467(8) 0.0498(9) 0.0802(13) -0.0199(9) 0.0126(8) -0.0088(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.9873(10) . ? Cu1 O1 1.9873(10) 3 ? Cu1 N1 2.0051(13) . ? Cu1 N1 2.0051(12) 3 ? N1 C5 1.337(2) . ? N1 C1 1.3427(19) . ? O1 C7 1.2750(18) . ? O2 C7 1.2364(19) . ? N2 O4 1.209(4) . ? N2 O3 1.211(4) . ? N2 C9 1.470(3) . ? C1 C2 1.377(2) . ? C1 H1 0.93(2) . ? C2 C3 1.377(3) . ? C2 H2 0.95(2) . ? C3 C4 1.388(3) . ? C3 C6 1.512(3) . ? C4 C5 1.374(3) . ? C4 H6 0.90(3) . ? C5 H5 1.05(3) . ? C6 H61 0.9600 . ? C6 H62 0.9600 . ? C6 H63 0.9600 . ? C7 C8 1.5018(19) . ? C8 C13 1.381(2) . ? C8 C9 1.386(2) . ? C9 C10 1.383(3) . ? C10 C11 1.369(4) . ? C10 H7 0.97(3) . ? C11 C12 1.365(4) . ? C11 H8 0.92(3) . ? C12 C13 1.391(3) . ? C12 H3 1.05(3) . ? C13 H4 0.96(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 O1 Cu1 O1 180.00 . 3 ? O1 Cu1 N1 89.24(5) . . ? O1 Cu1 N1 90.76(5) 3 . ? O1 Cu1 N1 90.76(5) . 3 ? O1 Cu1 N1 89.24(5) 3 3 ? N1 Cu1 N1 180.00 . 3 ? C5 N1 C1 117.38(14) . . ? C5 N1 Cu1 121.39(11) . . ? C1 N1 Cu1 121.23(11) . . ? C7 O1 Cu1 101.04(9) . . ? O4 N2 O3 124.5(3) . . ? O4 N2 C9 118.2(2) . . ? O3 N2 C9 117.3(3) . . ? N1 C1 C2 122.66(16) . . ? N1 C1 H1 116.6(12) . . ? C2 C1 H1 120.7(12) . . ? C3 C2 C1 120.06(16) . . ? C3 C2 H2 120.7(15) . . ? C1 C2 H2 119.2(15) . . ? C2 C3 C4 117.07(17) . . ? C2 C3 C6 121.1(2) . . ? C4 C3 C6 121.8(2) . . ? C5 C4 C3 119.95(19) . . ? C5 C4 H6 120.2(17) . . ? C3 C4 H6 119.6(17) . . ? N1 C5 C4 122.82(17) . . ? N1 C5 H5 117.8(15) . . ? C4 C5 H5 119.4(15) . . ? C3 C6 H61 109.5 . . ? C3 C6 H62 109.5 . . ? H61 C6 H62 109.5 . . ? C3 C6 H63 109.5 . . ? H61 C6 H63 109.5 . . ? H62 C6 H63 109.5 . . ? O2 C7 O1 123.65(13) . . ? O2 C7 C8 119.11(14) . . ? O1 C7 C8 117.01(13) . . ? C13 C8 C9 116.90(15) . . ? C13 C8 C7 119.67(14) . . ? C9 C8 C7 122.69(14) . . ? C10 C9 C8 122.63(18) . . ? C10 C9 N2 117.83(18) . . ? C8 C9 N2 119.52(17) . . ? C11 C10 C9 118.84(19) . . ? C11 C10 H7 118.7(19) . . ? C9 C10 H7 122.4(19) . . ? C12 C11 C10 120.33(19) . . ? C12 C11 H8 118.4(17) . . ? C10 C11 H8 121.3(17) . . ? C11 C12 C13 120.3(2) . . ? C11 C12 H3 116.8(16) . . ? C13 C12 H3 122.9(16) . . ? C8 C13 C12 121.00(18) . . ? C8 C13 H4 119.0(15) . . ? C12 C13 H4 120.0(15) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 30.04 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.313 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 915710' ####################################################################### # # 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_comp2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H26 Cu N4 O10' _chemical_formula_sum 'C26 H26 Cu N4 O10' _chemical_formula_weight 618.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 8.0020(2) _cell_length_b 12.2397(3) _cell_length_c 14.5180(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.1790(11) _cell_angle_gamma 90.00 _cell_volume 1372.32(6) _cell_formula_units_Z 2 _cell_measurement_temperature 295 _cell_measurement_reflns_used 16455 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 638 _exptl_absorpt_coefficient_mu 0.860 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.801 _exptl_absorpt_correction_T_max 0.886 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _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 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16455 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 5.20 _diffrn_reflns_theta_max 28.00 _reflns_number_total 3294 _reflns_number_gt 2519 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Kappa CCD server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al.,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997); WINGX (Farrugia, 1999) ; _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^)+(0.0789P)^2^+0.3938P] 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 0.029(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3294 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1358 _refine_ls_wR_factor_gt 0.1217 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.0000 0.0000 0.0617(2) Uani 1 2 d S . . N1 N 0.5581(3) 0.09744(16) 0.11427(14) 0.0555(5) Uani 1 1 d . . . O1W O 0.7801(3) 0.07475(19) -0.05667(16) 0.0721(5) Uani 1 1 d . . . O1 O 0.3768(2) 0.11996(14) -0.08026(11) 0.0604(4) Uani 1 1 d . . . O2 O 0.1436(2) 0.12672(14) -0.02370(13) 0.0626(5) Uani 1 1 d . . . C1 C 0.5357(3) 0.0624(2) 0.19770(17) 0.0563(6) Uani 1 1 d . . . H1 H 0.4947 -0.0083 0.2004 0.068 Uiso 1 1 calc R . . C2 C 0.5696(3) 0.1243(2) 0.27978(18) 0.0651(7) Uani 1 1 d . . . C3 C 0.6306(4) 0.2279(3) 0.2745(2) 0.0791(9) Uani 1 1 d . . . H3 H 0.6544 0.2729 0.3279 0.095 Uiso 1 1 calc R . . C4 C 0.6565(4) 0.2654(2) 0.1902(3) 0.0848(9) Uani 1 1 d . . . H4 H 0.6998 0.3353 0.1866 0.102 Uiso 1 1 calc R . . C5 C 0.6177(4) 0.1980(2) 0.1101(2) 0.0705(7) Uani 1 1 d . . . H5 H 0.6337 0.2238 0.0528 0.085 Uiso 1 1 calc R . . C6 C 0.5409(5) 0.0804(3) 0.3695(2) 0.0928(11) Uani 1 1 d . . . H61 H 0.5281 0.1399 0.4102 0.111 Uiso 1 1 calc R . . H62 H 0.6383 0.0364 0.4013 0.111 Uiso 1 1 calc R . . H63 H 0.4379 0.0366 0.3551 0.111 Uiso 1 1 calc R . . C7 C 0.2344(3) 0.15910(15) -0.07567(13) 0.0416(4) Uani 1 1 d . . . C8 C 0.1675(2) 0.25284(15) -0.14213(13) 0.0386(4) Uani 1 1 d . . . C9 C 0.0894(3) 0.34349(16) -0.11420(14) 0.0427(4) Uani 1 1 d . . . C10 C 0.0186(3) 0.42732(19) -0.17489(17) 0.0551(5) Uani 1 1 d . . . H10 H -0.0339 0.4864 -0.1535 0.066 Uiso 1 1 calc R . . C11 C 0.0277(3) 0.4213(2) -0.26891(17) 0.0607(6) Uani 1 1 d . . . H11 H -0.0169 0.4776 -0.3113 0.073 Uiso 1 1 calc R . . C12 C 0.1027(3) 0.3321(2) -0.29926(15) 0.0583(6) Uani 1 1 d . . . H12 H 0.1067 0.3278 -0.3626 0.070 Uiso 1 1 calc R . . C13 C 0.1723(3) 0.24858(18) -0.23698(14) 0.0474(5) Uani 1 1 d . . . H13 H 0.2230 0.1889 -0.2588 0.057 Uiso 1 1 calc R . . N2 N 0.0870(3) 0.35491(15) -0.01358(14) 0.0564(5) Uani 1 1 d . . . O3 O 0.2234(3) 0.34947(19) 0.04647(13) 0.0819(6) Uani 1 1 d . . . O4 O -0.0508(4) 0.3709(2) 0.00407(16) 0.0999(9) Uani 1 1 d . . . H1W H 0.878(5) 0.112(3) -0.050(3) 0.093(11) Uiso 1 1 d . . . H2W H 0.812(6) 0.003(3) -0.040(3) 0.099(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0771(3) 0.0584(3) 0.0410(2) -0.00575(16) 0.00019(19) 0.0331(2) N1 0.0543(10) 0.0539(10) 0.0518(10) -0.0064(8) 0.0019(8) 0.0150(8) O1W 0.0605(11) 0.0617(11) 0.0900(14) 0.0134(10) 0.0122(10) 0.0102(9) O1 0.0704(10) 0.0623(10) 0.0466(8) 0.0035(7) 0.0122(7) 0.0292(8) O2 0.0687(11) 0.0533(9) 0.0651(10) 0.0191(8) 0.0166(8) -0.0052(8) C1 0.0513(12) 0.0617(14) 0.0513(12) -0.0109(10) 0.0050(9) 0.0115(10) C2 0.0540(13) 0.0769(17) 0.0558(13) -0.0200(12) -0.0007(10) 0.0192(12) C3 0.0733(17) 0.0770(19) 0.0734(18) -0.0301(15) -0.0048(14) 0.0157(14) C4 0.082(2) 0.0521(14) 0.109(3) -0.0150(16) 0.0055(17) 0.0025(13) C5 0.0728(16) 0.0577(15) 0.0745(17) -0.0001(13) 0.0078(13) 0.0106(12) C6 0.091(2) 0.119(3) 0.0640(17) -0.0179(18) 0.0133(15) 0.029(2) C7 0.0514(11) 0.0344(9) 0.0351(9) -0.0032(7) 0.0042(8) 0.0020(7) C8 0.0396(9) 0.0388(9) 0.0364(8) 0.0001(7) 0.0080(7) 0.0005(7) C9 0.0499(11) 0.0397(9) 0.0392(9) 0.0015(8) 0.0127(8) 0.0030(8) C10 0.0642(13) 0.0449(11) 0.0572(12) 0.0085(10) 0.0175(10) 0.0143(10) C11 0.0698(15) 0.0586(13) 0.0510(12) 0.0205(10) 0.0107(11) 0.0110(11) C12 0.0672(14) 0.0702(15) 0.0367(10) 0.0088(10) 0.0124(9) 0.0029(11) C13 0.0536(11) 0.0519(11) 0.0372(9) -0.0025(8) 0.0131(8) 0.0039(9) N2 0.0874(14) 0.0400(9) 0.0461(10) -0.0010(7) 0.0254(10) 0.0060(9) O3 0.1074(16) 0.0894(14) 0.0421(9) -0.0082(9) 0.0076(10) -0.0226(12) O4 0.1212(19) 0.120(2) 0.0783(14) 0.0110(13) 0.0611(14) 0.0464(16) _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 O1 1.9707(15) . ? Cu1 O1 1.9707(15) 3_655 ? Cu1 N1 1.9968(19) . ? Cu1 N1 1.9968(19) 3_655 ? N1 C5 1.327(4) . ? N1 C1 1.340(3) . ? O1W H1W 0.89(4) . ? O1W H2W 0.93(4) . ? O1 C7 1.254(3) . ? O2 C7 1.242(3) . ? C1 C2 1.378(3) . ? C1 H1 0.9300 . ? C2 C3 1.368(5) . ? C2 C6 1.480(5) . ? C3 C4 1.372(5) . ? C3 H3 0.9300 . ? C4 C5 1.393(4) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 H61 0.9600 . ? C6 H62 0.9600 . ? C6 H63 0.9600 . ? C7 C8 1.504(3) . ? C8 C9 1.385(3) . ? C8 C13 1.389(3) . ? C9 C10 1.374(3) . ? C9 N2 1.473(3) . ? C10 C11 1.388(3) . ? C10 H10 0.9300 . ? C11 C12 1.373(4) . ? C11 H11 0.9300 . ? C12 C13 1.382(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? N2 O4 1.211(3) . ? N2 O3 1.208(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 O1 Cu1 O1 180.00 . 3_655 ? O1 Cu1 N1 91.02(7) . . ? O1 Cu1 N1 88.98(7) 3_655 . ? O1 Cu1 N1 88.98(7) . 3_655 ? O1 Cu1 N1 91.02(7) 3_655 3_655 ? N1 Cu1 N1 180.00 . 3_655 ? C5 N1 C1 118.2(2) . . ? C5 N1 Cu1 121.62(19) . . ? C1 N1 Cu1 120.16(17) . . ? H1W O1W H2W 106(4) . . ? C7 O1 Cu1 125.03(15) . . ? N1 C1 C2 124.3(3) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C3 C2 C1 116.9(3) . . ? C3 C2 C6 121.7(3) . . ? C1 C2 C6 121.4(3) . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 119.6(3) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 121.0(3) . . ? N1 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C2 C6 H61 109.5 . . ? C2 C6 H62 109.5 . . ? H61 C6 H62 109.5 . . ? C2 C6 H63 109.5 . . ? H61 C6 H63 109.5 . . ? H62 C6 H63 109.5 . . ? O2 C7 O1 126.51(19) . . ? O2 C7 C8 117.81(18) . . ? O1 C7 C8 115.66(18) . . ? C9 C8 C13 116.89(18) . . ? C9 C8 C7 122.35(17) . . ? C13 C8 C7 120.64(17) . . ? C10 C9 C8 123.51(19) . . ? C10 C9 N2 117.06(19) . . ? C8 C9 N2 119.38(17) . . ? C9 C10 C11 118.2(2) . . ? C9 C10 H10 120.9 . . ? C11 C10 H10 120.9 . . ? C12 C11 C10 119.9(2) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 120.9(2) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C12 C13 C8 120.7(2) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? O4 N2 O3 123.9(2) . . ? O4 N2 C9 118.3(2) . . ? O3 N2 C9 117.8(2) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.322 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 915711' ####################################################################### # # 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_comp3 #TrackingRef 'nitrobenzoate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(mu2-(2-hydroxyethylamino ethanolato)-bis(2-nitrobenzoate)-di copper(II)dihydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H36 Cu2 N4 O14, 2(H2 O)' _chemical_formula_sum 'C26 H40 Cu2 N4 O16' _chemical_formula_weight 791.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.6633(2) _cell_length_b 27.2585(7) _cell_length_c 8.5840(2) _cell_angle_alpha 90.00 _cell_angle_beta 117.5840(11) _cell_angle_gamma 90.00 _cell_volume 1589.29(7) _cell_formula_units_Z 2 _cell_measurement_temperature 295 _cell_measurement_reflns_used 6658 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.0 _exptl_crystal_description plate _exptl_crystal_colour 'light blue' _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 1.420 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.629 _exptl_absorpt_correction_T_max 0.852 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _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 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6658 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0554 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3325 _reflns_number_gt 2884 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Kappa CCD server software (Nonius, 1997)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al.,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997); WINGX (Farrugia, 1999) ; _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^)+(0.1036P)^2^+0.6274P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3325 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1415 _refine_ls_wR_factor_gt 0.1304 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.52639(5) 0.053118(11) 0.01477(4) 0.02482(16) Uani 1 1 d . . . O1 O 0.4769(3) -0.00065(6) 0.1383(3) 0.0281(4) Uani 1 1 d . . . N1 N 0.5898(3) 0.09274(8) 0.2365(3) 0.0277(5) Uani 1 1 d . . . N2 N 0.2408(4) 0.21718(9) -0.4875(4) 0.0348(6) Uani 1 1 d . . . O2 O 0.1886(3) 0.09093(8) -0.0601(3) 0.0370(5) Uani 1 1 d . . . O3 O 0.8908(4) 0.05106(9) 0.1788(4) 0.0430(6) Uani 1 1 d . . . O4 O 0.5655(3) 0.10499(8) -0.1252(3) 0.0359(5) Uani 1 1 d . . . O5 O 0.2838(4) 0.14623(11) -0.2605(4) 0.0584(8) Uani 1 1 d . . . O6 O 0.1277(4) 0.19238(12) -0.6104(4) 0.0601(7) Uani 1 1 d . . . O7 O 0.1918(4) 0.25005(11) -0.4208(4) 0.0625(8) Uani 1 1 d . . . C1 C 0.5815(5) 0.05794(11) 0.3677(4) 0.0347(6) Uani 1 1 d . . . H1A H 0.4571 0.0618 0.3704 0.042 Uiso 1 1 calc R . . H1B H 0.6866 0.0655 0.4837 0.042 Uiso 1 1 calc R . . C2 C 0.6023(5) 0.00518(10) 0.3213(4) 0.0329(6) Uani 1 1 d . . . H2A H 0.7377 -0.0016 0.3486 0.040 Uiso 1 1 calc R . . H2B H 0.5641 -0.0173 0.3878 0.040 Uiso 1 1 calc R . . C3 C 0.4467(4) 0.13334(11) 0.1969(4) 0.0340(6) Uani 1 1 d . . . H3A H 0.4724 0.1580 0.1287 0.041 Uiso 1 1 calc R . . H3B H 0.4678 0.1484 0.3066 0.041 Uiso 1 1 calc R . . C4 C 0.2311(5) 0.11755(14) 0.0958(4) 0.0412(7) Uani 1 1 d . . . H4A H 0.1987 0.0973 0.1718 0.049 Uiso 1 1 calc R . . H4B H 0.1482 0.1465 0.0653 0.049 Uiso 1 1 calc R . . C5 C 0.7904(4) 0.11497(12) 0.3035(4) 0.0374(7) Uani 1 1 d . . . H5A H 0.8226 0.1324 0.4119 0.045 Uiso 1 1 calc R . . H5B H 0.7888 0.1386 0.2183 0.045 Uiso 1 1 calc R . . C6 C 0.9471(4) 0.07745(13) 0.3368(4) 0.0398(7) Uani 1 1 d . . . H6A H 1.0729 0.0934 0.3720 0.048 Uiso 1 1 calc R . . H6B H 0.9598 0.0554 0.4301 0.048 Uiso 1 1 calc R . . C7 C 0.4567(4) 0.13794(10) -0.2253(4) 0.0279(5) Uani 1 1 d . . . C8 C 0.5525(4) 0.17088(9) -0.3052(3) 0.0245(5) Uani 1 1 d . . . C9 C 0.4540(4) 0.20899(10) -0.4208(4) 0.0265(5) Uani 1 1 d . . . C10 C 0.5458(5) 0.24085(12) -0.4834(4) 0.0348(7) Uani 1 1 d . . . C11 C 0.7454(5) 0.23492(12) -0.4313(5) 0.0383(7) Uani 1 1 d . . . C12 C 0.8466(5) 0.19733(12) -0.3184(5) 0.0378(7) Uani 1 1 d . . . C13 C 0.7523(4) 0.16602(11) -0.2559(4) 0.0320(6) Uani 1 1 d . . . O1W O -0.1366(4) 0.02384(12) -0.2073(3) 0.0476(6) Uani 1 1 d . . . H2 H 0.199(6) 0.1109(15) -0.131(5) 0.047(11) Uiso 1 1 d . . . H3 H 0.961(8) 0.0336(18) 0.184(7) 0.065(15) Uiso 1 1 d . . . H4 H 0.955(8) 0.1882(18) -0.292(7) 0.072(15) Uiso 1 1 d . . . H5 H 0.811(5) 0.1411(14) -0.184(5) 0.038(9) Uiso 1 1 d . . . H6 H 0.798(7) 0.2540(17) -0.490(6) 0.062(12) Uiso 1 1 d . . . H7 H 0.482(5) 0.2620(15) -0.561(5) 0.036(9) Uiso 1 1 d . . . H1W H -0.193(8) 0.021(2) -0.146(7) 0.077(16) Uiso 1 1 d . . . H2W H -0.059(9) 0.0476(19) -0.170(7) 0.073(18) 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 Cu1 0.0348(2) 0.0200(2) 0.0259(2) 0.00279(11) 0.01939(17) 0.00049(11) O1 0.0409(10) 0.0232(11) 0.0253(10) 0.0024(7) 0.0196(9) -0.0018(7) N1 0.0313(11) 0.0248(11) 0.0302(12) -0.0006(9) 0.0170(9) -0.0009(9) N2 0.0325(12) 0.0327(13) 0.0400(14) 0.0103(11) 0.0174(11) 0.0019(10) O2 0.0393(11) 0.0378(12) 0.0381(12) 0.0036(9) 0.0214(10) -0.0047(9) O3 0.0357(12) 0.0441(15) 0.0475(15) -0.0075(10) 0.0178(11) 0.0063(10) O4 0.0414(11) 0.0309(11) 0.0452(12) 0.0155(9) 0.0283(10) 0.0063(9) O5 0.0413(12) 0.0718(18) 0.0735(19) 0.0441(15) 0.0362(13) 0.0168(12) O6 0.0412(13) 0.0700(19) 0.0556(17) -0.0030(14) 0.0109(12) -0.0175(12) O7 0.0468(14) 0.0599(18) 0.085(2) -0.0047(15) 0.0341(15) 0.0149(12) C1 0.0480(17) 0.0334(15) 0.0276(14) -0.0003(11) 0.0216(13) -0.0038(12) C2 0.0463(16) 0.0285(14) 0.0263(14) 0.0039(10) 0.0187(13) -0.0006(11) C3 0.0412(15) 0.0280(14) 0.0397(16) -0.0057(12) 0.0246(13) 0.0018(11) C4 0.0369(15) 0.049(2) 0.0467(18) 0.0003(15) 0.0274(14) 0.0053(13) C5 0.0363(14) 0.0358(16) 0.0422(17) -0.0086(13) 0.0199(13) -0.0081(12) C6 0.0302(13) 0.0447(19) 0.0415(17) -0.0062(14) 0.0141(13) -0.0027(12) C7 0.0365(13) 0.0246(13) 0.0279(13) 0.0031(10) 0.0194(11) 0.0004(10) C8 0.0312(12) 0.0199(12) 0.0272(12) -0.0005(9) 0.0176(11) -0.0012(9) C9 0.0311(13) 0.0232(13) 0.0294(13) 0.0009(10) 0.0175(11) -0.0003(10) C10 0.0429(16) 0.0291(16) 0.0376(16) 0.0075(12) 0.0230(14) -0.0005(12) C11 0.0436(16) 0.0330(16) 0.0502(18) 0.0057(13) 0.0317(15) -0.0052(12) C12 0.0340(14) 0.0370(16) 0.0490(18) -0.0001(14) 0.0250(14) -0.0010(12) C13 0.0335(14) 0.0294(14) 0.0374(15) 0.0060(12) 0.0202(12) 0.0053(11) O1W 0.0423(13) 0.0599(18) 0.0432(14) -0.0037(12) 0.0219(11) 0.0083(12) _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 O1 1.934(2) 3_655 ? Cu1 O1 1.9463(19) . ? Cu1 O4 1.9659(19) . ? Cu1 N1 2.042(2) . ? Cu1 Cu1 2.9187(6) 3_655 ? O1 C2 1.421(4) . ? O1 Cu1 1.934(2) 3_655 ? N1 C3 1.483(4) . ? N1 C1 1.496(4) . ? N1 C5 1.498(4) . ? N2 O7 1.213(4) . ? N2 O6 1.214(4) . ? N2 C9 1.477(3) . ? O2 C4 1.422(4) . ? O2 H2 0.85(4) . ? O3 C6 1.414(4) . ? O3 H3 0.71(5) . ? O4 C7 1.256(3) . ? O5 C7 1.236(4) . ? C1 C2 1.520(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.529(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.501(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.511(4) . ? C8 C9 1.393(4) . ? C8 C13 1.393(4) . ? C9 C10 1.374(4) . ? C10 C11 1.390(4) . ? C10 H7 0.84(4) . ? C11 C12 1.376(5) . ? C11 H6 0.93(5) . ? C12 C13 1.378(4) . ? C12 H4 0.79(5) . ? C13 H5 0.88(4) . ? O1W H1W 0.82(6) . ? O1W H2W 0.83(6) . ? 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 Cu1 O1 82.46(10) 3_655 . ? O1 Cu1 O4 94.27(9) 3_655 . ? O1 Cu1 O4 176.05(9) . . ? O1 Cu1 N1 161.24(10) 3_655 . ? O1 Cu1 N1 85.00(9) . . ? O4 Cu1 N1 98.70(9) . . ? O1 Cu1 Cu1 41.38(6) 3_655 3_655 ? O1 Cu1 Cu1 41.07(6) . 3_655 ? O4 Cu1 Cu1 135.61(7) . 3_655 ? N1 Cu1 Cu1 124.71(7) . 3_655 ? C2 O1 Cu1 128.53(17) . 3_655 ? C2 O1 Cu1 108.38(16) . . ? Cu1 O1 Cu1 97.54(10) 3_655 . ? C3 N1 C1 111.2(2) . . ? C3 N1 C5 107.8(2) . . ? C1 N1 C5 111.2(2) . . ? C3 N1 Cu1 110.47(18) . . ? C1 N1 Cu1 106.95(17) . . ? C5 N1 Cu1 109.33(17) . . ? O7 N2 O6 124.7(3) . . ? O7 N2 C9 117.2(3) . . ? O6 N2 C9 118.0(3) . . ? C4 O2 H2 107(3) . . ? C6 O3 H3 114(4) . . ? C7 O4 Cu1 133.78(19) . . ? N1 C1 C2 110.9(2) . . ? N1 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? O1 C2 C1 107.2(2) . . ? O1 C2 H2A 110.3 . . ? C1 C2 H2A 110.3 . . ? O1 C2 H2B 110.3 . . ? C1 C2 H2B 110.3 . . ? H2A C2 H2B 108.5 . . ? N1 C3 C4 114.2(2) . . ? N1 C3 H3A 108.7 . . ? C4 C3 H3A 108.7 . . ? N1 C3 H3B 108.7 . . ? C4 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? O2 C4 C3 113.2(2) . . ? O2 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? O2 C4 H4B 108.9 . . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? N1 C5 C6 112.7(3) . . ? N1 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? N1 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? O3 C6 C5 107.6(3) . . ? O3 C6 H6A 110.2 . . ? C5 C6 H6A 110.2 . . ? O3 C6 H6B 110.2 . . ? C5 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? O5 C7 O4 126.5(3) . . ? O5 C7 C8 118.1(2) . . ? O4 C7 C8 115.3(2) . . ? C9 C8 C13 116.4(2) . . ? C9 C8 C7 123.3(2) . . ? C13 C8 C7 120.1(2) . . ? C10 C9 C8 122.9(3) . . ? C10 C9 N2 115.3(2) . . ? C8 C9 N2 121.8(2) . . ? C9 C10 C11 119.1(3) . . ? C9 C10 H7 122(2) . . ? C11 C10 H7 119(2) . . ? C12 C11 C10 119.4(3) . . ? C12 C11 H6 124(3) . . ? C10 C11 H6 116(3) . . ? C11 C12 C13 120.6(3) . . ? C11 C12 H4 127(4) . . ? C13 C12 H4 111(4) . . ? C12 C13 C8 121.6(3) . . ? C12 C13 H5 124(2) . . ? C8 C13 H5 115(2) . . ? H1W O1W H2W 108(5) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.542 _refine_diff_density_min -1.031 _refine_diff_density_rms 0.177 _database_code_depnum_ccdc_archive 'CCDC 915712'