#------------------------------------------------------------------------------ #$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $ #$Revision: 14 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/1100160.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1100160 _journal_name_full 'Polyhedron' _journal_volume 23 _journal_page_first 1505 _journal_page_last 1518 _journal_year 2004 _publ_section_title ; 'Solid state coordination chemistry of mononuclear mixed-ligand complexes of Ni(II), Cu(II) and Zn(II) with \a-hydroxycarboxylic acids and imidazole' ; loop_ _publ_author_name 'Carballo, Rosa' 'Vazquez-Lopez, Ezequiel M.' 'Covelo, Berta' 'Garcia-Martinez, Emilia' 'Castineiras, Alfonso' 'Niclos, Juan' _chemical_formula_sum 'C11 H18 Cu N2 O6' _chemical_formula_weight 337.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 P2(1)/n 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 9.6623(15) _cell_length_b 17.630(3) _cell_length_c 9.7978(16) _cell_angle_alpha 90.00 _cell_angle_beta 118.748(3) _cell_angle_gamma 90.00 _cell_volume 1463.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 1.518 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8787 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8121 _diffrn_reflns_av_R_equivalents 0.0736 _diffrn_reflns_av_sigmaI/netI 0.2177 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 28.00 _reflns_number_total 3293 _reflns_number_gt 1411 _reflns_threshold_expression >2sigma(I) _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary patterson _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom&difmap' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3293 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1503 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.0634 _refine_ls_wR_factor_gt 0.0511 _refine_ls_goodness_of_fit_ref 0.694 _refine_ls_restrained_S_all 0.694 _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 Cu Cu 0.47359(6) 0.79480(3) 0.05160(7) 0.03203(15) Uani 1 1 d . . . O11 O 0.3755(3) 0.70760(16) -0.0789(3) 0.0331(7) Uani 1 1 d . . . O12 O 0.3248(3) 0.58449(14) -0.1005(3) 0.0369(8) Uani 1 1 d . . . O13 O 0.5382(3) 0.69875(16) 0.2237(3) 0.0343(8) Uani 1 1 d . . . C11 C 0.3992(5) 0.6407(3) -0.0238(5) 0.0280(11) Uani 1 1 d . . . C12 C 0.5260(5) 0.6277(2) 0.1448(5) 0.0314(11) Uani 1 1 d . . . C13 C 0.4812(5) 0.5637(2) 0.2207(5) 0.0516(14) Uani 1 1 d . . . H13A H 0.5615 0.5584 0.3273 0.077 Uiso 1 1 calc R . . H13B H 0.4717 0.5172 0.1660 0.077 Uiso 1 1 calc R . . H13C H 0.3823 0.5753 0.2167 0.077 Uiso 1 1 calc R . . C14 C 0.6823(4) 0.6107(2) 0.1476(5) 0.0491(13) Uani 1 1 d . . . H14A H 0.7111 0.6529 0.1045 0.074 Uiso 1 1 calc R . . H14B H 0.6711 0.5661 0.0869 0.074 Uiso 1 1 calc R . . H14C H 0.7630 0.6024 0.2530 0.074 Uiso 1 1 calc R . . O21 O 0.2704(3) 0.82048(14) 0.0381(3) 0.0348(8) Uani 1 1 d . . . O22 O 0.1519(3) 0.89599(16) 0.1314(4) 0.0554(10) Uani 1 1 d . . . O23 O 0.5391(3) 0.88380(15) 0.1866(3) 0.0395(8) Uani 1 1 d . . . C21 C 0.2703(5) 0.8749(2) 0.1259(5) 0.0349(11) Uani 1 1 d . . . C22 C 0.4257(5) 0.9136(2) 0.2306(5) 0.0343(11) Uani 1 1 d . . . C23 C 0.4134(5) 0.9976(2) 0.2041(6) 0.0772(19) Uani 1 1 d . . . H23A H 0.5125 1.0210 0.2732 0.116 Uiso 1 1 calc R . . H23B H 0.3323 1.0176 0.2238 0.116 Uiso 1 1 calc R . . H23C H 0.3876 1.0079 0.0983 0.116 Uiso 1 1 calc R . . C24 C 0.4784(5) 0.8937(3) 0.3982(5) 0.0720(17) Uani 1 1 d . . . H24A H 0.4970 0.8401 0.4130 0.108 Uiso 1 1 calc R . . H24B H 0.3976 0.9079 0.4238 0.108 Uiso 1 1 calc R . . H24C H 0.5739 0.9206 0.4645 0.108 Uiso 1 1 calc R . . N1 N 0.6366(4) 0.80589(19) -0.0134(4) 0.0332(9) Uani 1 1 d . . . N2 N 0.8517(5) 0.8356(2) -0.0221(5) 0.0439(11) Uani 1 1 d . . . C1 C 0.7731(5) 0.8405(2) 0.0594(5) 0.0373(12) Uani 1 1 d . . . H1 H 0.8106 0.8652 0.1546 0.045 Uiso 1 1 calc R . . C2 C 0.6273(5) 0.7781(3) -0.1473(6) 0.0533(15) Uani 1 1 d . . . H2 H 0.5427 0.7509 -0.2229 0.064 Uiso 1 1 calc R . . C3 C 0.7609(5) 0.7965(3) -0.1529(6) 0.0526(13) Uani 1 1 d . . . H3 H 0.7848 0.7845 -0.2316 0.063 Uiso 1 1 calc R . . H23 H 0.648(4) 0.889(2) 0.258(5) 0.055(14) Uiso 1 1 d . . . H13 H 0.623(4) 0.699(2) 0.325(4) 0.049(13) Uiso 1 1 d . . . H20 H 0.956(5) 0.856(2) 0.016(6) 0.088(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 Cu 0.0277(3) 0.0372(3) 0.0309(3) -0.0053(3) 0.0138(2) -0.0044(3) O11 0.0350(16) 0.0299(16) 0.0313(19) 0.0031(16) 0.0133(14) -0.0044(15) O12 0.0324(17) 0.0298(18) 0.033(2) -0.0067(15) 0.0034(15) -0.0022(14) O13 0.0314(17) 0.0348(18) 0.0263(19) -0.0072(18) 0.0056(15) 0.0027(16) C11 0.024(2) 0.040(3) 0.027(3) -0.005(2) 0.018(2) -0.003(2) C12 0.032(3) 0.026(3) 0.040(3) -0.003(2) 0.020(3) 0.000(2) C13 0.066(3) 0.041(3) 0.040(3) -0.001(3) 0.020(3) -0.006(2) C14 0.034(3) 0.053(3) 0.052(4) -0.005(3) 0.014(3) 0.010(2) O21 0.0254(16) 0.043(2) 0.032(2) -0.0066(15) 0.0112(15) -0.0041(13) O22 0.0316(19) 0.082(2) 0.056(2) -0.0179(19) 0.0236(18) 0.0007(17) O23 0.0197(17) 0.0484(19) 0.045(2) -0.0160(17) 0.0107(17) -0.0021(15) C21 0.031(3) 0.042(3) 0.031(3) 0.004(2) 0.014(2) 0.004(2) C22 0.027(3) 0.042(3) 0.037(3) -0.011(2) 0.018(2) -0.004(2) C23 0.060(4) 0.040(3) 0.140(6) -0.019(4) 0.055(4) -0.006(3) C24 0.051(3) 0.122(5) 0.041(4) -0.026(3) 0.020(3) -0.016(3) N1 0.029(2) 0.043(2) 0.032(3) -0.007(2) 0.0183(19) -0.0063(18) N2 0.033(3) 0.056(3) 0.045(3) 0.007(2) 0.021(2) 0.002(2) C1 0.033(3) 0.047(3) 0.030(3) 0.000(2) 0.014(3) 0.000(2) C2 0.054(3) 0.065(4) 0.051(4) -0.028(3) 0.034(3) -0.027(3) C3 0.062(3) 0.059(3) 0.057(4) -0.015(3) 0.044(3) -0.009(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O11 1.932(3) . ? Cu O23 1.951(3) . ? Cu O21 1.956(3) . ? Cu N1 1.973(3) . ? Cu O13 2.256(3) . ? O11 C11 1.271(4) . ? O12 C11 1.242(4) . ? O13 C12 1.447(4) . ? C11 C12 1.529(5) . ? C12 C13 1.523(5) . ? C12 C14 1.527(5) . ? O21 C21 1.289(4) . ? O22 C21 1.228(4) . ? O23 C22 1.454(4) . ? C21 C22 1.514(5) . ? C22 C23 1.498(5) . ? C22 C24 1.509(6) . ? N1 C1 1.310(4) . ? N1 C2 1.362(5) . ? N2 C3 1.344(5) . ? N2 C1 1.344(5) . ? C2 C3 1.358(5) . ? 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 O11 Cu O23 169.96(11) . . ? O11 Cu O21 88.99(11) . . ? O23 Cu O21 81.22(11) . . ? O11 Cu N1 94.54(12) . . ? O23 Cu N1 95.18(13) . . ? O21 Cu N1 152.45(12) . . ? O11 Cu O13 76.64(10) . . ? O23 Cu O13 102.35(11) . . ? O21 Cu O13 97.60(10) . . ? N1 Cu O13 109.81(12) . . ? C11 O11 Cu 121.8(3) . . ? C12 O13 Cu 109.2(2) . . ? O12 C11 O11 123.3(4) . . ? O12 C11 C12 117.6(4) . . ? O11 C11 C12 119.1(4) . . ? O13 C12 C13 110.5(3) . . ? O13 C12 C14 109.5(3) . . ? C13 C12 C14 110.9(3) . . ? O13 C12 C11 105.3(3) . . ? C13 C12 C11 111.7(3) . . ? C14 C12 C11 108.7(3) . . ? C21 O21 Cu 116.8(3) . . ? C22 O23 Cu 116.5(2) . . ? O22 C21 O21 123.7(4) . . ? O22 C21 C22 118.4(4) . . ? O21 C21 C22 117.9(4) . . ? O23 C22 C23 108.3(3) . . ? O23 C22 C24 109.3(3) . . ? C23 C22 C24 112.0(4) . . ? O23 C22 C21 106.2(3) . . ? C23 C22 C21 111.0(3) . . ? C24 C22 C21 109.8(4) . . ? C1 N1 C2 106.0(3) . . ? C1 N1 Cu 128.4(3) . . ? C2 N1 Cu 125.6(3) . . ? C3 N2 C1 107.7(4) . . ? N1 C1 N2 110.8(4) . . ? C3 C2 N1 109.2(4) . . ? N2 C3 C2 106.4(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O23 H23 O12 0.94(4) 1.67(4) 2.597(4) 166(3) 4_676 O13 H13 O21 0.93(4) 1.91(4) 2.827(4) 167(3) 4_676 N2 H20 O22 0.96(4) 1.82(4) 2.759(5) 166(4) 1_655 C1 H1 O12 0.93 2.50 3.391(5) 160.7 4_676 _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 0.495 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.068