# 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_orto _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(mu2-(2-hydroxyethylamino ethanolato)-bis(o-methoxybenzoate)-di copper(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H42 Cu2 N2 O12' _chemical_formula_sum 'C28 H42 Cu2 N2 O12' _chemical_formula_weight 725.72 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 10.9061(2) _cell_length_b 8.5014(3) _cell_length_c 16.9111(5) _cell_angle_alpha 90.0000 _cell_angle_beta 95.5220(12) _cell_angle_gamma 90.0000 _cell_volume 1560.67(8) _cell_formula_units_Z 2 _cell_measurement_temperature 295 _cell_measurement_reflns_used 12691 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 28. _exptl_crystal_description prismatic _exptl_crystal_colour violet _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 1.427 _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 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 12691 _diffrn_reflns_av_R_equivalents 0.0746 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 28.00 _reflns_number_total 3751 _reflns_number_gt 2598 _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^)+(0.0761P)^2^+1.7286P] 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 3751 _refine_ls_number_parameters 203 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1662 _refine_ls_wR_factor_gt 0.1395 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 0.09824(5) 0.48192(5) 0.06547(3) 0.04060(19) Uani 1 1 d . . . O1 O 0.2374(3) 0.5967(3) 0.11448(18) 0.0504(7) Uani 1 1 d . . . O2 O 0.1334(3) 0.7936(5) 0.1632(2) 0.0698(10) Uani 1 1 d . . . O3 O -0.0528(3) 0.3842(3) 0.02552(19) 0.0553(8) Uani 1 1 d . . . O4 O 0.2333(3) 0.3156(4) 0.00271(18) 0.0578(8) Uani 1 1 d D . . O5 O 0.1113(3) 0.2863(5) 0.36612(17) 0.0631(9) Uani 1 1 d . . . O6 O 0.3073(4) 0.8642(5) 0.2974(2) 0.0746(11) Uani 1 1 d . . . N1 N 0.1121(3) 0.2959(4) 0.14415(19) 0.0424(8) Uani 1 1 d . . . C1 C 0.0033(5) 0.1931(6) 0.1228(3) 0.0590(12) Uani 1 1 d . . . H11 H 0.0296 0.0841 0.1252 0.071 Uiso 1 1 calc R . . H12 H -0.0556 0.2076 0.1616 0.071 Uiso 1 1 calc R . . C2 C -0.0579(5) 0.2258(6) 0.0430(3) 0.0639(14) Uani 1 1 d . . . H21 H -0.0180 0.1662 0.0038 0.077 Uiso 1 1 calc R . . H22 H -0.1433 0.1925 0.0404 0.077 Uiso 1 1 calc R . . C3 C 0.2328(5) 0.2194(6) 0.1354(2) 0.0558(12) Uani 1 1 d . . . H31 H 0.2386 0.1235 0.1666 0.067 Uiso 1 1 calc R . . H32 H 0.2984 0.2890 0.1565 0.067 Uiso 1 1 calc R . . C4 C 0.2512(6) 0.1803(6) 0.0504(3) 0.0664(14) Uani 1 1 d . . . H41 H 0.3339 0.1401 0.0474 0.080 Uiso 1 1 calc R . . H42 H 0.1932 0.0993 0.0310 0.080 Uiso 1 1 calc R . . C5 C 0.1119(5) 0.3533(5) 0.2275(2) 0.0487(10) Uani 1 1 d . . . H51 H 0.0311 0.3961 0.2344 0.058 Uiso 1 1 calc R . . H52 H 0.1710 0.4384 0.2358 0.058 Uiso 1 1 calc R . . C6 C 0.1426(5) 0.2290(6) 0.2907(2) 0.0547(11) Uani 1 1 d . . . H61 H 0.0967 0.1336 0.2767 0.066 Uiso 1 1 calc R . . H62 H 0.2298 0.2044 0.2939 0.066 Uiso 1 1 calc R . . C7 C 0.2290(4) 0.7302(5) 0.1475(2) 0.0451(9) Uani 1 1 d . . . C8 C 0.3509(4) 0.8141(5) 0.1660(3) 0.0457(9) Uani 1 1 d . . . C9 C 0.4292(5) 0.8281(6) 0.1062(3) 0.0563(11) Uani 1 1 d . . . H9 H 0.4090 0.7785 0.0576 0.068 Uiso 1 1 calc R . . C10 C 0.5366(5) 0.9147(7) 0.1178(4) 0.0728(15) Uani 1 1 d . . . H10 H 0.5875 0.9252 0.0770 0.087 Uiso 1 1 calc R . . C11 C 0.5678(5) 0.9850(7) 0.1898(4) 0.0724(16) Uani 1 1 d . . . H11A H 0.6394 1.0447 0.1975 0.087 Uiso 1 1 calc R . . C12 C 0.4939(5) 0.9683(6) 0.2510(4) 0.0663(14) Uani 1 1 d . . . H12A H 0.5173 1.0133 0.3003 0.080 Uiso 1 1 calc R . . C13 C 0.3854(5) 0.8848(5) 0.2390(3) 0.0521(11) Uani 1 1 d . . . C14 C 0.3470(8) 0.9135(9) 0.3756(4) 0.099(2) Uani 1 1 d . . . H141 H 0.4146 0.8490 0.3967 0.119 Uiso 1 1 calc R . . H142 H 0.2803 0.9037 0.4084 0.119 Uiso 1 1 calc R . . H143 H 0.3731 1.0213 0.3747 0.119 Uiso 1 1 calc R . . H4 H 0.201(5) 0.307(7) -0.0446(16) 0.067(16) Uiso 1 1 d D . . H5 H 0.0365 0.2933 0.3438 0.103 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 0.0533(3) 0.0343(3) 0.0323(3) 0.00346(18) -0.00560(19) -0.0031(2) O1 0.0615(19) 0.0391(15) 0.0481(16) -0.0019(12) -0.0080(14) -0.0023(13) O2 0.052(2) 0.076(2) 0.081(2) -0.025(2) 0.0025(17) -0.0011(17) O3 0.071(2) 0.0393(15) 0.0511(17) 0.0123(13) -0.0167(15) -0.0127(14) O4 0.080(2) 0.0578(19) 0.0349(16) -0.0018(14) 0.0020(15) 0.0043(16) O5 0.068(2) 0.091(3) 0.0302(15) 0.0081(15) 0.0046(14) 0.0058(18) O6 0.096(3) 0.076(2) 0.053(2) -0.0149(18) 0.0080(19) 0.001(2) N1 0.054(2) 0.0393(17) 0.0324(16) 0.0027(13) -0.0034(14) -0.0001(14) C1 0.080(3) 0.044(2) 0.051(3) 0.0100(19) -0.004(2) -0.014(2) C2 0.081(4) 0.048(3) 0.059(3) 0.014(2) -0.014(2) -0.018(2) C3 0.079(3) 0.049(2) 0.038(2) 0.0032(18) 0.000(2) 0.019(2) C4 0.092(4) 0.060(3) 0.047(3) -0.004(2) 0.006(2) 0.023(3) C5 0.066(3) 0.045(2) 0.035(2) 0.0021(17) 0.0032(18) 0.0031(19) C6 0.071(3) 0.056(3) 0.037(2) 0.0091(19) 0.006(2) 0.004(2) C7 0.052(3) 0.045(2) 0.036(2) 0.0001(16) -0.0030(17) -0.0005(18) C8 0.049(2) 0.038(2) 0.049(2) 0.0004(17) -0.0022(18) 0.0051(17) C9 0.058(3) 0.057(3) 0.054(3) -0.001(2) 0.004(2) -0.001(2) C10 0.058(3) 0.076(4) 0.087(4) 0.008(3) 0.018(3) -0.004(3) C11 0.052(3) 0.063(3) 0.098(5) -0.001(3) -0.013(3) -0.009(2) C12 0.069(3) 0.050(3) 0.074(3) -0.010(2) -0.021(3) -0.006(2) C13 0.061(3) 0.041(2) 0.052(3) -0.0040(18) -0.005(2) 0.0012(19) C14 0.145(7) 0.097(5) 0.053(3) -0.016(3) -0.007(4) 0.005(5) _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 1.910(3) . ? Cu1 O1 1.923(3) . ? Cu1 O3 1.940(3) 3_565 ? Cu1 N1 2.063(3) . ? Cu1 O4 2.365(3) . ? Cu1 Cu1 2.9455(9) 3_565 ? O1 C7 1.272(5) . ? O2 C7 1.225(6) . ? O3 C2 1.381(5) . ? O3 Cu1 1.940(3) 3_565 ? O4 C4 1.408(6) . ? O4 H4 0.846(19) . ? O5 C6 1.437(5) . ? O5 H5 0.87 . ? O6 C13 1.377(6) . ? O6 C14 1.414(6) . ? N1 C3 1.488(6) . ? N1 C1 1.489(6) . ? N1 C5 1.493(5) . ? C1 C2 1.474(6) . ? C1 H11 0.9700 . ? C1 H12 0.9700 . ? C2 H21 0.9700 . ? C2 H22 0.9700 . ? C3 C4 1.507(6) . ? C3 H31 0.9700 . ? C3 H32 0.9700 . ? C4 H41 0.9700 . ? C4 H42 0.9700 . ? C5 C6 1.516(6) . ? C5 H51 0.9700 . ? C5 H52 0.9700 . ? C6 H61 0.9700 . ? C6 H62 0.9700 . ? C7 C8 1.514(6) . ? C8 C9 1.391(7) . ? C8 C13 1.392(6) . ? C9 C10 1.382(7) . ? C9 H9 0.9300 . ? C10 C11 1.370(9) . ? C10 H10 0.9300 . ? C11 C12 1.378(9) . ? C11 H11A 0.9300 . ? C12 C13 1.378(7) . ? C12 H12A 0.9300 . ? C14 H141 0.9600 . ? C14 H142 0.9600 . ? C14 H143 0.9600 . ? 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 O1 172.37(15) . . ? O3 Cu1 O3 80.15(13) . 3_565 ? O1 Cu1 O3 100.06(13) . 3_565 ? O3 Cu1 N1 84.36(13) . . ? O1 Cu1 N1 96.05(13) . . ? O3 Cu1 N1 163.50(13) 3_565 . ? O3 Cu1 O4 97.72(15) . . ? O1 Cu1 O4 89.85(13) . . ? O3 Cu1 O4 96.75(14) 3_565 . ? N1 Cu1 O4 79.70(13) . . ? O3 Cu1 Cu1 40.45(9) . 3_565 ? O1 Cu1 Cu1 139.25(9) . 3_565 ? O3 Cu1 Cu1 39.70(9) 3_565 3_565 ? N1 Cu1 Cu1 124.59(10) . 3_565 ? O4 Cu1 Cu1 99.46(8) . 3_565 ? C7 O1 Cu1 123.7(3) . . ? C2 O3 Cu1 113.6(3) . . ? C2 O3 Cu1 136.8(3) . 3_565 ? Cu1 O3 Cu1 99.85(13) . 3_565 ? C4 O4 Cu1 106.8(3) . . ? C4 O4 H4 120(4) . . ? Cu1 O4 H4 105(4) . . ? C6 O5 H5 86.00 . . ? C13 O6 C14 118.6(5) . . ? C3 N1 C1 114.3(4) . . ? C3 N1 C5 108.6(3) . . ? C1 N1 C5 110.4(4) . . ? C3 N1 Cu1 106.3(3) . . ? C1 N1 Cu1 106.6(2) . . ? C5 N1 Cu1 110.6(2) . . ? C2 C1 N1 113.1(4) . . ? C2 C1 H11 109.0 . . ? N1 C1 H11 109.0 . . ? C2 C1 H12 109.0 . . ? N1 C1 H12 109.0 . . ? H11 C1 H12 107.8 . . ? O3 C2 C1 110.8(4) . . ? O3 C2 H21 109.5 . . ? C1 C2 H21 109.5 . . ? O3 C2 H22 109.5 . . ? C1 C2 H22 109.5 . . ? H21 C2 H22 108.1 . . ? N1 C3 C4 113.1(4) . . ? N1 C3 H31 109.0 . . ? C4 C3 H31 109.0 . . ? N1 C3 H32 109.0 . . ? C4 C3 H32 109.0 . . ? H31 C3 H32 107.8 . . ? O4 C4 C3 110.0(4) . . ? O4 C4 H41 109.7 . . ? C3 C4 H41 109.7 . . ? O4 C4 H42 109.7 . . ? C3 C4 H42 109.7 . . ? H41 C4 H42 108.2 . . ? N1 C5 C6 114.6(4) . . ? N1 C5 H51 108.6 . . ? C6 C5 H51 108.6 . . ? N1 C5 H52 108.6 . . ? C6 C5 H52 108.6 . . ? H51 C5 H52 107.6 . . ? O5 C6 C5 109.5(4) . . ? O5 C6 H61 109.8 . . ? C5 C6 H61 109.8 . . ? O5 C6 H62 109.8 . . ? C5 C6 H62 109.8 . . ? H61 C6 H62 108.2 . . ? O2 C7 O1 125.8(4) . . ? O2 C7 C8 119.8(4) . . ? O1 C7 C8 114.3(4) . . ? C9 C8 C13 118.4(4) . . ? C9 C8 C7 118.6(4) . . ? C13 C8 C7 122.9(4) . . ? C10 C9 C8 120.9(5) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C11 C10 C9 119.5(6) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.6(5) . . ? C10 C11 H11A 119.7 . . ? C12 C11 H11A 119.7 . . ? C11 C12 C13 119.9(5) . . ? C11 C12 H12A 120.1 . . ? C13 C12 H12A 120.1 . . ? O6 C13 C12 122.8(5) . . ? O6 C13 C8 116.6(4) . . ? C12 C13 C8 120.6(5) . . ? O6 C14 H141 109.5 . . ? O6 C14 H142 109.5 . . ? H141 C14 H142 109.5 . . ? O6 C14 H143 109.5 . . ? H141 C14 H143 109.5 . . ? H142 C14 H143 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.045 _refine_diff_density_min -0.797 _refine_diff_density_rms 0.096 _database_code_depnum_ccdc_archive 'CCDC 874506' ####################################################################### # # 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_meta _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(mu2-(2-hydroxyethylamino ethanolato)-bis(m-methoxybenzoate)-di copper(II)dihydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H42 Cu2 N2 O12 , 2(H2 O)' _chemical_formula_sum 'C28 H46 Cu2 N2 O14' _chemical_formula_weight 761.75 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5706(2) _cell_length_b 8.3360(2) _cell_length_c 15.0758(4) _cell_angle_alpha 96.1220(10) _cell_angle_beta 99.6270(10) _cell_angle_gamma 114.9430(10) _cell_volume 833.65(4) _cell_formula_units_Z 1 _cell_measurement_temperature 295 _cell_measurement_reflns_used 1349 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 398 _exptl_absorpt_coefficient_mu 1.344 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.870 _exptl_absorpt_correction_T_max 0.946 _exptl_absorpt_process_details ; SORTAV (R.H. Blessing, Acta Crystallogr. 1995, A51, 33) ; _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 13490 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 30.06 _reflns_number_total 4815 _reflns_number_gt 4087 _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^)+(0.0601P)^2^+0.1673P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4815 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _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 0.06454(3) 0.52849(2) 0.099673(12) 0.03064(8) Uani 1 1 d . . . O1 O 0.2888(2) 0.70438(18) 0.19752(9) 0.0409(3) Uani 1 1 d . . . O2 O 0.1783(2) 0.8906(2) 0.25917(11) 0.0528(4) Uani 1 1 d . . . O3 O -0.15953(18) 0.35955(16) 0.00045(8) 0.0337(2) Uani 1 1 d . . . O4 O 0.2697(3) 0.3600(2) 0.09645(11) 0.0486(3) Uani 1 1 d . . . O5 O -0.1674(2) 0.6306(2) 0.16924(10) 0.0453(3) Uani 1 1 d . . . O6 O 0.7725(3) 1.3116(2) 0.52265(11) 0.0697(5) Uani 1 1 d . . . N1 N -0.0484(2) 0.33812(19) 0.17716(9) 0.0331(3) Uani 1 1 d . . . C1 C 0.1981(3) 0.2232(3) 0.14790(16) 0.0459(4) Uani 1 1 d . . . C2 C 0.1103(3) 0.2888(3) 0.21785(14) 0.0422(4) Uani 1 1 d . . . C3 C -0.2440(3) 0.5013(3) 0.22330(18) 0.0507(5) Uani 1 1 d . . . C4 C -0.1090(3) 0.4141(3) 0.25358(13) 0.0418(4) Uani 1 1 d . . . C5 C -0.2090(3) 0.1818(2) 0.01431(12) 0.0378(4) Uani 1 1 d . . . C6 C -0.2240(3) 0.1802(3) 0.11408(13) 0.0415(4) Uani 1 1 d . . . C7 C 0.3095(3) 0.8400(2) 0.25332(11) 0.0350(3) Uani 1 1 d . . . C8 C 0.5132(3) 0.9429(2) 0.31844(11) 0.0340(3) Uani 1 1 d . . . C9 C 0.6675(3) 0.8989(3) 0.31017(13) 0.0417(4) Uani 1 1 d . . . C10 C 0.8518(3) 0.9919(3) 0.37344(15) 0.0493(5) Uani 1 1 d . . . C11 C 0.8808(3) 1.1276(3) 0.44343(15) 0.0518(5) Uani 1 1 d . . . C12 C 0.7277(3) 1.1729(3) 0.45113(13) 0.0466(5) Uani 1 1 d . . . C13 C 0.5426(3) 1.0818(2) 0.38872(12) 0.0389(4) Uani 1 1 d . . . C14 C 0.6325(7) 1.3801(5) 0.5244(2) 0.0828(10) Uani 1 1 d . . . O1W O -0.4127(3) 0.7272(2) 0.04313(13) 0.0501(4) Uani 1 1 d . . . H1 H 0.304(4) 0.197(3) 0.1831(16) 0.049(6) Uiso 1 1 d . . . H2 H 0.102(4) 0.117(3) 0.1129(16) 0.045(6) Uiso 1 1 d . . . H3 H 0.213(4) 0.392(3) 0.2565(16) 0.044(6) Uiso 1 1 d . . . H4 H 0.306(4) 0.330(4) 0.0618(18) 0.049(7) Uiso 1 1 d . . . H5 H -0.105(4) 0.147(3) -0.0011(16) 0.044(6) Uiso 1 1 d . . . H6 H 0.059(4) 0.201(4) 0.2507(17) 0.050(6) Uiso 1 1 d . . . H7 H 0.643(4) 0.800(3) 0.2582(16) 0.046(6) Uiso 1 1 d . . . H8 H -0.371(4) 0.413(4) 0.1877(17) 0.049(6) Uiso 1 1 d . . . H9 H -0.270(4) 0.555(4) 0.2793(18) 0.056(7) Uiso 1 1 d . . . H10 H 0.956(4) 0.964(3) 0.3656(17) 0.052(6) Uiso 1 1 d . . . H11 H -0.526(5) 0.679(4) 0.038(2) 0.062(9) Uiso 1 1 d . . . H12 H -0.361(5) 0.702(4) 0.083(2) 0.062(9) Uiso 1 1 d . . . H13 H 0.435(4) 1.102(3) 0.3926(15) 0.044(6) Uiso 1 1 d . . . H14 H 0.598(5) 1.416(4) 0.468(2) 0.073(9) Uiso 1 1 d . . . H15 H 0.494(6) 1.276(6) 0.534(3) 0.103(13) Uiso 1 1 d . . . H16 H 0.706(5) 1.499(5) 0.574(2) 0.089(10) Uiso 1 1 d . . . H17 H -0.069(6) 0.715(5) 0.201(2) 0.086(11) Uiso 1 1 d . . . H18 H 0.015(3) 0.507(3) 0.2916(14) 0.033(5) Uiso 1 1 d . . . H19 H -0.178(4) 0.329(4) 0.2825(17) 0.050(6) Uiso 1 1 d . . . H20 H 0.988(5) 1.181(4) 0.482(2) 0.067(8) Uiso 1 1 d . . . H21 H -0.336(3) 0.101(3) -0.0274(15) 0.036(5) Uiso 1 1 d . . . H22 H -0.345(4) 0.189(4) 0.1275(18) 0.060(7) Uiso 1 1 d . . . H23 H -0.235(3) 0.070(3) 0.1347(15) 0.042(6) 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 0.02901(12) 0.02584(11) 0.02768(11) 0.00231(7) 0.00560(8) 0.00466(8) O1 0.0354(7) 0.0370(6) 0.0362(6) -0.0062(5) 0.0027(5) 0.0084(5) O2 0.0393(7) 0.0407(7) 0.0673(10) -0.0072(7) -0.0018(7) 0.0171(6) O3 0.0320(6) 0.0273(5) 0.0310(6) 0.0041(4) 0.0052(4) 0.0046(5) O4 0.0564(9) 0.0494(8) 0.0545(9) 0.0192(7) 0.0284(7) 0.0296(7) O5 0.0388(7) 0.0435(7) 0.0494(8) 0.0068(6) 0.0048(6) 0.0172(6) O6 0.0787(12) 0.0589(10) 0.0463(9) -0.0176(7) -0.0107(8) 0.0233(9) N1 0.0307(7) 0.0328(7) 0.0328(7) 0.0073(5) 0.0085(5) 0.0109(6) C1 0.0473(11) 0.0421(10) 0.0563(12) 0.0163(9) 0.0166(9) 0.0242(9) C2 0.0426(10) 0.0456(10) 0.0415(9) 0.0164(8) 0.0112(8) 0.0203(9) C3 0.0415(11) 0.0509(12) 0.0658(13) 0.0135(10) 0.0243(10) 0.0217(10) C4 0.0442(10) 0.0463(10) 0.0357(9) 0.0117(8) 0.0166(8) 0.0176(9) C5 0.0384(9) 0.0250(7) 0.0379(9) 0.0030(6) 0.0069(7) 0.0045(7) C6 0.0394(10) 0.0310(8) 0.0412(9) 0.0085(7) 0.0098(7) 0.0033(7) C7 0.0357(9) 0.0282(7) 0.0337(8) 0.0042(6) 0.0038(6) 0.0095(7) C8 0.0342(8) 0.0300(8) 0.0300(7) 0.0041(6) 0.0048(6) 0.0085(7) C9 0.0427(10) 0.0418(9) 0.0379(9) 0.0055(7) 0.0077(7) 0.0176(8) C10 0.0394(10) 0.0586(12) 0.0504(11) 0.0154(9) 0.0077(8) 0.0226(10) C11 0.0393(10) 0.0546(12) 0.0415(10) 0.0082(9) -0.0072(8) 0.0090(9) C12 0.0537(12) 0.0378(9) 0.0312(8) 0.0005(7) 0.0012(8) 0.0091(9) C13 0.0396(10) 0.0347(9) 0.0355(8) 0.0019(7) 0.0074(7) 0.0119(7) C14 0.122(3) 0.0675(18) 0.0516(15) -0.0165(13) 0.0000(16) 0.050(2) O1W 0.0461(9) 0.0478(8) 0.0633(10) 0.0168(7) 0.0232(8) 0.0224(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 O3 1.9402(12) 2_565 ? Cu1 O3 1.9456(12) . ? Cu1 O1 1.9519(12) . ? Cu1 N1 2.0492(15) . ? Cu1 Cu1 2.9213(4) 2_565 ? O1 C7 1.271(2) . ? O2 C7 1.244(2) . ? O3 C5 1.415(2) . ? O3 Cu1 1.9402(12) 2_565 ? O4 C1 1.416(3) . ? O4 H4 0.70(3) . ? O5 C3 1.408(3) . ? O5 H17 0.80(4) . ? O6 C12 1.377(2) . ? O6 C14 1.402(4) . ? N1 C4 1.485(2) . ? N1 C2 1.488(2) . ? N1 C6 1.496(2) . ? C1 C2 1.507(3) . ? C1 H1 1.00(2) . ? C1 H2 0.90(3) . ? C2 H3 0.93(2) . ? C2 H6 0.91(3) . ? C3 C4 1.524(3) . ? C3 H8 0.95(3) . ? C3 H9 1.00(3) . ? C4 H18 0.96(2) . ? C4 H19 0.89(3) . ? C5 C6 1.528(3) . ? C5 H5 1.00(2) . ? C5 H21 0.96(2) . ? C6 H22 1.00(3) . ? C6 H23 0.97(2) . ? C7 C8 1.509(2) . ? C8 C9 1.384(3) . ? C8 C13 1.398(2) . ? C9 C10 1.394(3) . ? C9 H7 1.01(2) . ? C10 C11 1.378(3) . ? C10 H10 0.93(3) . ? C11 C12 1.380(3) . ? C11 H20 0.83(3) . ? C12 C13 1.391(3) . ? C13 H13 0.91(2) . ? C14 H14 0.96(3) . ? C14 H15 1.08(4) . ? C14 H16 1.04(4) . ? O1W H11 0.76(3) . ? O1W H12 0.76(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 O3 Cu1 O3 82.51(5) 2_565 . ? O3 Cu1 O1 96.21(6) 2_565 . ? O3 Cu1 O1 178.16(5) . . ? O3 Cu1 N1 161.47(6) 2_565 . ? O3 Cu1 N1 85.18(5) . . ? O1 Cu1 N1 96.38(6) . . ? O3 Cu1 Cu1 41.32(3) 2_565 2_565 ? O3 Cu1 Cu1 41.18(4) . 2_565 ? O1 Cu1 Cu1 137.52(4) . 2_565 ? N1 Cu1 Cu1 125.01(4) . 2_565 ? C7 O1 Cu1 132.36(12) . . ? C5 O3 Cu1 129.58(11) . 2_565 ? C5 O3 Cu1 108.80(10) . . ? Cu1 O3 Cu1 97.49(5) 2_565 . ? C1 O4 H4 109(2) . . ? C3 O5 H17 108(3) . . ? C12 O6 C14 117.28(19) . . ? C4 N1 C2 107.94(14) . . ? C4 N1 C6 111.39(15) . . ? C2 N1 C6 111.93(15) . . ? C4 N1 Cu1 109.69(11) . . ? C2 N1 Cu1 109.25(11) . . ? C6 N1 Cu1 106.62(10) . . ? O4 C1 C2 107.01(16) . . ? O4 C1 H1 114.6(14) . . ? C2 C1 H1 106.4(13) . . ? O4 C1 H2 112.8(15) . . ? C2 C1 H2 108.7(15) . . ? H1 C1 H2 107(2) . . ? N1 C2 C1 113.74(16) . . ? N1 C2 H3 107.1(14) . . ? C1 C2 H3 107.9(15) . . ? N1 C2 H6 109.5(16) . . ? C1 C2 H6 108.7(15) . . ? H3 C2 H6 110(2) . . ? O5 C3 C4 113.96(17) . . ? O5 C3 H8 106.3(15) . . ? C4 C3 H8 110.9(15) . . ? O5 C3 H9 111.2(15) . . ? C4 C3 H9 108.3(14) . . ? H8 C3 H9 106(2) . . ? N1 C4 C3 113.98(16) . . ? N1 C4 H18 104.3(12) . . ? C3 C4 H18 107.7(12) . . ? N1 C4 H19 111.6(16) . . ? C3 C4 H19 105.4(16) . . ? H18 C4 H19 114(2) . . ? O3 C5 C6 107.19(14) . . ? O3 C5 H5 108.9(14) . . ? C6 C5 H5 113.3(13) . . ? O3 C5 H21 108.3(13) . . ? C6 C5 H21 111.0(13) . . ? H5 C5 H21 108.1(18) . . ? N1 C6 C5 110.64(14) . . ? N1 C6 H22 105.4(15) . . ? C5 C6 H22 114.4(15) . . ? N1 C6 H23 108.6(13) . . ? C5 C6 H23 114.6(13) . . ? H22 C6 H23 103(2) . . ? O2 C7 O1 126.07(16) . . ? O2 C7 C8 119.02(15) . . ? O1 C7 C8 114.89(16) . . ? C9 C8 C13 120.37(17) . . ? C9 C8 C7 120.85(15) . . ? C13 C8 C7 118.76(16) . . ? C8 C9 C10 119.53(18) . . ? C8 C9 H7 118.6(14) . . ? C10 C9 H7 121.9(14) . . ? C11 C10 C9 120.3(2) . . ? C11 C10 H10 121.2(16) . . ? C9 C10 H10 118.5(16) . . ? C10 C11 C12 120.22(18) . . ? C10 C11 H20 121(2) . . ? C12 C11 H20 119(2) . . ? O6 C12 C11 115.74(19) . . ? O6 C12 C13 123.8(2) . . ? C11 C12 C13 120.43(18) . . ? C12 C13 C8 119.15(19) . . ? C12 C13 H13 124.0(14) . . ? C8 C13 H13 116.7(15) . . ? O6 C14 H14 113.3(18) . . ? O6 C14 H15 109(2) . . ? H14 C14 H15 106(3) . . ? O6 C14 H16 105.4(19) . . ? H14 C14 H16 105(3) . . ? H15 C14 H16 118(3) . . ? H11 O1W H12 110(3) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.271 _refine_diff_density_min -0.577 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 874507' ####################################################################### # # 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_para #TrackingRef 'CuBinuclear.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(mu2-(2-hydroxyethylamino ethanolato)-bis(p-methoxybenzoate)-di copper(II)dihydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H42 Cu2 N2 O12, 2(H2 O)' _chemical_formula_sum 'C28 H46 Cu2 N2 O14' _chemical_formula_weight 761.75 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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.60940(10) _cell_length_b 8.0937(2) _cell_length_c 14.6853(4) _cell_angle_alpha 102.8580(8) _cell_angle_beta 92.3380(8) _cell_angle_gamma 110.5400(13) _cell_volume 818.68(3) _cell_formula_units_Z 1 _cell_measurement_temperature 295 _cell_measurement_reflns_used 13108 _cell_measurement_theta_min 3. _cell_measurement_theta_max 30. _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 398 _exptl_absorpt_coefficient_mu 1.369 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.814 _exptl_absorpt_correction_T_max 0.875 _exptl_absorpt_process_details ; SORTAV (R.H. Blessing, Acta Crystallogr. 1995, A51, 33) ; _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 13108 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0337 _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 -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 30.01 _reflns_number_total 4747 _reflns_number_gt 4206 _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^)+(0.0506P)^2^+0.1310P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4747 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0907 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.48795(2) 0.44447(2) 0.397731(11) 0.03085(7) Uani 1 1 d . . . O3 O 0.35183(15) 0.35821(15) 0.49779(8) 0.0333(2) Uani 1 1 d . . . O4 O 0.19973(19) 0.49428(19) 0.33133(10) 0.0455(3) Uani 1 1 d . . . O5 O 0.7045(2) 0.27683(19) 0.39629(11) 0.0492(3) Uani 1 1 d . . . O1 O 0.62714(18) 0.53964(18) 0.29975(9) 0.0420(3) Uani 1 1 d . . . O2 O 0.4467(2) 0.6579(2) 0.23219(12) 0.0583(4) Uani 1 1 d . . . O6 O 1.0981(2) 0.7840(3) -0.02556(11) 0.0653(4) Uani 1 1 d . . . O1W O 0.0405(2) 0.6978(2) 0.46274(13) 0.0520(3) Uani 1 1 d . . . N1 N 0.33043(18) 0.18750(17) 0.31554(9) 0.0335(3) Uani 1 1 d . . . C1 C 0.2205(2) 0.0810(2) 0.37898(12) 0.0408(3) Uani 1 1 d . . . C2 C 0.3093(2) 0.1686(2) 0.48187(12) 0.0376(3) Uani 1 1 d . . . C3 C 0.2034(3) 0.2018(3) 0.24056(12) 0.0433(4) Uani 1 1 d . . . C4 C 0.0884(3) 0.3170(3) 0.27624(17) 0.0515(4) Uani 1 1 d . . . C5 C 0.4612(3) 0.1041(2) 0.27006(13) 0.0419(3) Uani 1 1 d . . . C6 C 0.6085(3) 0.0974(3) 0.33942(15) 0.0460(4) Uani 1 1 d . . . C7 C 0.5915(2) 0.6204(2) 0.24097(12) 0.0379(3) Uani 1 1 d . . . C8 C 0.7354(2) 0.6689(2) 0.17471(12) 0.0378(3) Uani 1 1 d . . . C9 C 0.6932(3) 0.7328(4) 0.09961(16) 0.0604(6) Uani 1 1 d . . . C10 C 0.8184(4) 0.7702(4) 0.03445(17) 0.0663(6) Uani 1 1 d . . . C11 C 0.9870(3) 0.7451(3) 0.04366(13) 0.0468(4) Uani 1 1 d . . . C12 C 1.0345(2) 0.6847(2) 0.11942(13) 0.0407(3) Uani 1 1 d . . . C13 C 0.9071(2) 0.6473(2) 0.18412(12) 0.0381(3) Uani 1 1 d . . . C14 C 1.2810(4) 0.7772(4) -0.0156(2) 0.0700(7) Uani 1 1 d . . . H1 H 0.213(3) -0.041(3) 0.3548(16) 0.049(6) Uiso 1 1 d . . . H2 H 0.000(4) 0.264(3) 0.3187(18) 0.056(6) Uiso 1 1 d . . . H3 H 0.389(3) -0.010(4) 0.2318(18) 0.054(6) Uiso 1 1 d . . . H4 H 0.289(3) 0.265(3) 0.2002(16) 0.045(5) Uiso 1 1 d . . . H5 H 0.522(3) 0.176(3) 0.2323(17) 0.049(6) Uiso 1 1 d . . . H6 H 1.150(4) 0.666(4) 0.1306(18) 0.060(7) Uiso 1 1 d . . . H7 H 0.422(3) 0.140(3) 0.4921(16) 0.046(6) Uiso 1 1 d . . . H8 H 0.553(3) 0.019(3) 0.3732(15) 0.037(5) Uiso 1 1 d . . . H9 H 0.941(3) 0.605(3) 0.2373(17) 0.051(6) Uiso 1 1 d . . . H10 H 0.776(5) 0.808(5) -0.018(2) 0.098(11) Uiso 1 1 d . . . H11 H 0.582(5) 0.748(4) 0.096(2) 0.089(10) Uiso 1 1 d . . . H12 H 1.329(5) 0.823(5) -0.069(3) 0.108(12) Uiso 1 1 d . . . H13 H 1.354(5) 0.862(5) 0.044(3) 0.094(10) Uiso 1 1 d . . . H14 H 1.271(4) 0.648(5) -0.016(2) 0.086(10) Uiso 1 1 d . . . H15 H 0.088(3) 0.076(3) 0.3704(16) 0.047(5) Uiso 1 1 d . . . H16 H 0.223(3) 0.119(3) 0.5266(15) 0.039(5) Uiso 1 1 d . . . H17 H 0.114(3) 0.081(3) 0.2093(16) 0.049(6) Uiso 1 1 d . . . H18 H 0.020(4) 0.327(4) 0.2240(19) 0.059(7) Uiso 1 1 d . . . H19 H 0.260(4) 0.543(4) 0.299(2) 0.067(8) Uiso 1 1 d . . . H20 H 0.695(3) 0.052(3) 0.3026(17) 0.057(6) Uiso 1 1 d . . . H21 H 0.775(4) 0.280(3) 0.4291(18) 0.049(7) Uiso 1 1 d . . . H1W H -0.050(5) 0.655(5) 0.467(2) 0.073(10) Uiso 1 1 d . . . H2W H 0.061(4) 0.639(5) 0.417(2) 0.077(10) 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 0.03543(11) 0.02871(11) 0.02338(11) 0.00626(7) 0.00363(7) 0.00604(7) O3 0.0387(5) 0.0291(5) 0.0260(5) 0.0060(4) 0.0040(4) 0.0055(4) O4 0.0478(7) 0.0447(7) 0.0449(7) 0.0105(6) 0.0103(6) 0.0182(5) O5 0.0481(7) 0.0430(7) 0.0512(8) 0.0017(6) -0.0073(6) 0.0179(6) O1 0.0450(6) 0.0494(7) 0.0320(6) 0.0187(5) 0.0094(5) 0.0124(5) O2 0.0601(8) 0.0630(9) 0.0735(10) 0.0379(8) 0.0279(7) 0.0340(7) O6 0.0743(10) 0.0780(11) 0.0497(9) 0.0328(8) 0.0273(7) 0.0231(8) O1W 0.0434(7) 0.0463(8) 0.0601(10) 0.0071(7) 0.0005(6) 0.0136(6) N1 0.0366(6) 0.0311(6) 0.0274(6) 0.0037(5) 0.0012(5) 0.0089(5) C1 0.0431(8) 0.0305(7) 0.0384(8) 0.0067(6) 0.0048(6) 0.0022(6) C2 0.0455(8) 0.0308(7) 0.0329(8) 0.0110(6) 0.0062(6) 0.0080(6) C3 0.0486(9) 0.0399(8) 0.0326(8) 0.0013(7) -0.0078(7) 0.0122(7) C4 0.0410(9) 0.0511(10) 0.0587(12) 0.0110(9) -0.0050(8) 0.0157(8) C5 0.0491(9) 0.0366(8) 0.0349(8) -0.0009(7) 0.0051(7) 0.0159(7) C6 0.0476(9) 0.0386(9) 0.0508(10) 0.0050(8) 0.0049(8) 0.0188(7) C7 0.0476(8) 0.0308(7) 0.0343(8) 0.0094(6) 0.0098(6) 0.0122(6) C8 0.0481(8) 0.0343(7) 0.0330(8) 0.0128(6) 0.0087(6) 0.0146(6) C9 0.0657(12) 0.0874(16) 0.0544(12) 0.0429(12) 0.0198(10) 0.0435(12) C10 0.0783(15) 0.0933(18) 0.0513(12) 0.0474(13) 0.0203(11) 0.0413(13) C11 0.0587(10) 0.0446(9) 0.0354(8) 0.0159(7) 0.0144(7) 0.0127(8) C12 0.0435(8) 0.0354(8) 0.0389(8) 0.0088(6) 0.0057(6) 0.0096(6) C13 0.0465(8) 0.0346(7) 0.0322(8) 0.0124(6) 0.0043(6) 0.0115(6) C14 0.0596(13) 0.0706(16) 0.0578(14) 0.0076(12) 0.0230(11) 0.0013(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 1.9446(11) 2_666 ? Cu1 O3 1.9475(11) . ? Cu1 O1 1.9573(12) . ? Cu1 N1 2.0578(13) . ? Cu1 Cu1 2.9157(3) 2_666 ? O3 C2 1.4142(19) . ? O3 Cu1 1.9446(11) 2_666 ? O4 C4 1.416(2) . ? O4 H19 0.75(3) . ? O5 C6 1.416(2) . ? O5 H21 0.69(3) . ? O1 C7 1.266(2) . ? O2 C7 1.250(2) . ? O6 C11 1.369(2) . ? O6 C14 1.415(3) . ? O1W H1W 0.67(3) . ? O1W H2W 0.79(3) . ? N1 C3 1.486(2) . ? N1 C5 1.489(2) . ? N1 C1 1.492(2) . ? C1 C2 1.532(2) . ? C1 H1 0.95(2) . ? C1 H15 0.99(2) . ? C2 H7 0.98(2) . ? C2 H16 1.00(2) . ? C3 C4 1.517(3) . ? C3 H4 0.98(2) . ? C3 H17 0.97(2) . ? C4 H2 0.99(3) . ? C4 H18 0.95(3) . ? C5 C6 1.507(3) . ? C5 H3 0.92(3) . ? C5 H5 0.91(3) . ? C6 H8 0.89(2) . ? C6 H20 0.99(2) . ? C7 C8 1.502(2) . ? C8 C13 1.383(2) . ? C8 C9 1.388(2) . ? C9 C10 1.384(3) . ? C9 H11 0.90(3) . ? C10 C11 1.373(3) . ? C10 H10 0.98(4) . ? C11 C12 1.393(3) . ? C12 C13 1.390(2) . ? C12 H6 0.95(3) . ? C13 H9 0.98(2) . ? C14 H12 0.97(4) . ? C14 H13 0.98(4) . ? C14 H14 1.02(4) . ? 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 O3 82.97(5) 2_666 . ? O3 Cu1 O1 95.36(5) 2_666 . ? O3 Cu1 O1 178.06(5) . . ? O3 Cu1 N1 161.70(5) 2_666 . ? O3 Cu1 N1 84.50(5) . . ? O1 Cu1 N1 97.35(5) . . ? O3 Cu1 Cu1 41.52(3) 2_666 2_666 ? O3 Cu1 Cu1 41.45(3) . 2_666 ? O1 Cu1 Cu1 136.87(4) . 2_666 ? N1 Cu1 Cu1 124.69(4) . 2_666 ? C2 O3 Cu1 128.91(10) . 2_666 ? C2 O3 Cu1 109.11(9) . . ? Cu1 O3 Cu1 97.03(5) 2_666 . ? C4 O4 H19 107(2) . . ? C6 O5 H21 111(2) . . ? C7 O1 Cu1 132.29(11) . . ? C11 O6 C14 117.80(19) . . ? H1W O1W H2W 106(4) . . ? C3 N1 C5 108.54(13) . . ? C3 N1 C1 111.47(13) . . ? C5 N1 C1 111.65(14) . . ? C3 N1 Cu1 109.28(10) . . ? C5 N1 Cu1 108.76(10) . . ? C1 N1 Cu1 107.09(9) . . ? N1 C1 C2 110.83(12) . . ? N1 C1 H1 105.8(14) . . ? C2 C1 H1 115.4(14) . . ? N1 C1 H15 108.0(13) . . ? C2 C1 H15 110.8(13) . . ? H1 C1 H15 105.7(19) . . ? O3 C2 C1 107.08(13) . . ? O3 C2 H7 112.4(14) . . ? C1 C2 H7 108.7(13) . . ? O3 C2 H16 109.9(12) . . ? C1 C2 H16 112.2(12) . . ? H7 C2 H16 106.6(17) . . ? N1 C3 C4 114.21(15) . . ? N1 C3 H4 105.0(13) . . ? C4 C3 H4 106.8(13) . . ? N1 C3 H17 109.2(13) . . ? C4 C3 H17 106.7(13) . . ? H4 C3 H17 115.1(18) . . ? O4 C4 C3 113.57(15) . . ? O4 C4 H2 103.9(15) . . ? C3 C4 H2 112.1(14) . . ? O4 C4 H18 108.7(16) . . ? C3 C4 H18 108.7(15) . . ? H2 C4 H18 110(2) . . ? N1 C5 C6 113.37(14) . . ? N1 C5 H3 108.2(15) . . ? C6 C5 H3 112.5(15) . . ? N1 C5 H5 106.3(14) . . ? C6 C5 H5 108.2(15) . . ? H3 C5 H5 108(2) . . ? O5 C6 C5 107.62(15) . . ? O5 C6 H8 112.3(13) . . ? C5 C6 H8 109.8(13) . . ? O5 C6 H20 111.2(14) . . ? C5 C6 H20 107.2(14) . . ? H8 C6 H20 108.5(19) . . ? O2 C7 O1 125.86(16) . . ? O2 C7 C8 118.21(15) . . ? O1 C7 C8 115.90(15) . . ? C13 C8 C9 118.53(16) . . ? C13 C8 C7 122.31(15) . . ? C9 C8 C7 119.13(16) . . ? C10 C9 C8 120.7(2) . . ? C10 C9 H11 123(2) . . ? C8 C9 H11 116(2) . . ? C11 C10 C9 120.17(19) . . ? C11 C10 H10 124(2) . . ? C9 C10 H10 116(2) . . ? O6 C11 C10 115.02(18) . . ? O6 C11 C12 124.72(18) . . ? C10 C11 C12 120.27(17) . . ? C13 C12 C11 118.87(17) . . ? C13 C12 H6 116.5(16) . . ? C11 C12 H6 124.6(16) . . ? C8 C13 C12 121.41(15) . . ? C8 C13 H9 119.9(14) . . ? C12 C13 H9 118.7(14) . . ? O6 C14 H12 99(2) . . ? O6 C14 H13 110(2) . . ? H12 C14 H13 111(3) . . ? O6 C14 H14 109.9(18) . . ? H12 C14 H14 117(3) . . ? H13 C14 H14 109(3) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.289 _refine_diff_density_min -0.641 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 874508'