#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/46/2204682.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2204682 loop_ _publ_author_name 'Huiyan Liu' 'Haiying Wang' 'Dezhong Niu' 'Zaisheng Lu' _publ_section_title Bis[4-chloro-2-(2-hydroxyethyliminomethyl)phenolato-\k^2^N,O]copper(II) _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first m1941 _journal_page_last m1942 _journal_paper_doi 10.1107/S1600536804029733 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac '[Cu (C9 H9 Cl1 N1 O2)2]' _chemical_formula_moiety 'C18 H18 Cl2 Cu N2 O4' _chemical_formula_sum 'C18 H18 Cl2 Cu N2 O4' _chemical_formula_weight 460.78 _chemical_melting_point 208.2 _chemical_name_systematic ; Bis[4-chloro-2-(2-hydroxyethyliminomethyl)phenolato-\k^2^N,O]copper(II) ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 94.530(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 4.9589(12) _cell_length_b 16.872(4) _cell_length_c 10.711(2) _cell_measurement_reflns_used 3969 _cell_measurement_temperature 193(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.1 _cell_volume 893.4(3) _computing_cell_refinement CrystalClear _computing_data_collection 'CrystalClear (Pflugrath, 1999)' _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2000-2003)' _computing_molecular_graphics SHELXLTL _computing_publication_material SHELXLTL _computing_structure_refinement 'SHELXLTL (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 193(2) _diffrn_detector_area_resol_mean 7.31 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71070 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 9835 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 3.08 _exptl_absorpt_coefficient_mu 1.550 _exptl_absorpt_correction_T_max 0.8604 _exptl_absorpt_correction_T_min 0.6535 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_crystal_colour brown--yellow _exptl_crystal_density_diffrn 1.713 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 470 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.498 _refine_diff_density_min -0.377 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 2041 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.122 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0293 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0277P)^2^+0.5395P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0688 _refine_ls_wR_factor_ref 0.0710 _reflns_number_gt 1891 _reflns_number_total 2041 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fl6134.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2204682 _cod_database_fobs_code 2204682 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol Cu1 0.5000 0.5000 0.0000 0.01903(11) Uani d S 1 Cu Cl1 0.24967(11) 0.69286(3) 0.56722(4) 0.03247(14) Uani d . 1 Cl O1 0.7241(2) 0.53368(8) 0.14878(12) 0.0232(3) Uani d . 1 O O2 -0.1802(3) 0.54951(8) -0.15418(14) 0.0273(3) Uani d . 1 O N1 0.3215(3) 0.60612(9) -0.00483(14) 0.0178(3) Uani d . 1 N C1 0.6173(3) 0.57044(10) 0.24126(17) 0.0198(4) Uani d . 1 C C2 0.7210(4) 0.55794(12) 0.36644(18) 0.0259(4) Uani d . 1 C H2A 0.8705 0.5232 0.3829 0.031 Uiso calc R 1 H C3 0.6101(4) 0.59499(12) 0.46552(18) 0.0264(4) Uani d . 1 C H3 0.6805 0.5849 0.5491 0.032 Uiso calc R 1 H C4 0.3955(4) 0.64707(11) 0.44208(17) 0.0240(4) Uani d . 1 C C5 0.2930(4) 0.66310(11) 0.32139(17) 0.0220(4) Uani d . 1 C H5 0.1495 0.7001 0.3068 0.026 Uiso calc R 1 H C6 0.4002(4) 0.62484(10) 0.22008(17) 0.0198(4) Uani d . 1 C C7 0.2891(4) 0.64558(10) 0.09505(17) 0.0203(4) Uani d . 1 C H7 0.1832 0.6925 0.0865 0.024 Uiso calc R 1 H C8 0.2081(4) 0.64087(11) -0.12381(17) 0.0204(4) Uani d . 1 C H8A 0.2972 0.6163 -0.1937 0.024 Uiso calc R 1 H H8B 0.2495 0.6983 -0.1238 0.024 Uiso calc R 1 H C9 -0.0963(4) 0.62969(11) -0.14635(18) 0.0224(4) Uani d . 1 C H9A -0.1849 0.6556 -0.0775 0.027 Uiso calc R 1 H H9B -0.1593 0.6569 -0.2252 0.027 Uiso calc R 1 H H2 -0.054(6) 0.5202(16) -0.161(3) 0.043(8) Uiso d . 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu1 0.01829(17) 0.01942(17) 0.01909(17) 0.00285(11) -0.00031(12) -0.00253(11) Cl1 0.0415(3) 0.0363(3) 0.0207(2) -0.0041(2) 0.0099(2) -0.00546(19) O1 0.0193(6) 0.0266(7) 0.0232(7) 0.0031(5) -0.0010(5) -0.0061(5) O2 0.0179(6) 0.0221(7) 0.0420(8) 0.0000(6) 0.0039(6) -0.0034(6) N1 0.0160(7) 0.0205(7) 0.0171(7) -0.0011(6) 0.0018(6) 0.0013(6) C1 0.0184(8) 0.0189(8) 0.0220(9) -0.0035(7) 0.0008(7) -0.0023(7) C2 0.0248(9) 0.0264(10) 0.0255(10) 0.0002(8) -0.0040(8) 0.0003(8) C3 0.0305(10) 0.0280(10) 0.0199(9) -0.0065(8) -0.0025(8) 0.0011(7) C4 0.0293(10) 0.0233(9) 0.0200(9) -0.0072(8) 0.0062(8) -0.0028(7) C5 0.0235(9) 0.0187(9) 0.0240(9) -0.0012(7) 0.0040(7) -0.0012(7) C6 0.0218(9) 0.0185(9) 0.0193(9) -0.0022(7) 0.0018(7) -0.0008(7) C7 0.0195(8) 0.0176(8) 0.0240(9) 0.0015(7) 0.0041(7) 0.0001(7) C8 0.0217(9) 0.0216(9) 0.0179(9) -0.0004(7) 0.0017(7) 0.0033(7) C9 0.0203(9) 0.0224(9) 0.0242(9) 0.0009(7) 0.0007(7) 0.0012(7) 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' Cl Cl 0.1484 0.1585 '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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 Cu1 O1 3_665 . 180.00(7) yes O1 Cu1 N1 3_665 3_665 89.01(6) yes O1 Cu1 N1 . 3_665 90.99(6) yes O1 Cu1 N1 3_665 . 90.99(6) yes O1 Cu1 N1 . . 89.01(6) yes N1 Cu1 N1 3_665 . 180.0 yes C1 O1 Cu1 . . 120.96(11) ? C9 O2 H2 . . 111.4(19) ? C7 N1 C8 . . 116.81(15) ? C7 N1 Cu1 . . 121.95(12) ? C8 N1 Cu1 . . 121.17(11) ? O1 C1 C2 . . 120.41(16) ? O1 C1 C6 . . 122.02(16) ? C2 C1 C6 . . 117.56(17) ? C3 C2 C1 . . 121.59(18) ? C3 C2 H2A . . 119.2 ? C1 C2 H2A . . 119.2 ? C2 C3 C4 . . 119.54(18) ? C2 C3 H3 . . 120.2 ? C4 C3 H3 . . 120.2 ? C5 C4 C3 . . 120.99(18) ? C5 C4 Cl1 . . 119.16(15) ? C3 C4 Cl1 . . 119.85(15) ? C4 C5 C6 . . 120.06(18) ? C4 C5 H5 . . 120.0 ? C6 C5 H5 . . 120.0 ? C5 C6 C1 . . 120.20(17) ? C5 C6 C7 . . 117.62(16) ? C1 C6 C7 . . 122.13(16) ? N1 C7 C6 . . 125.61(16) ? N1 C7 H7 . . 117.2 ? C6 C7 H7 . . 117.2 ? N1 C8 C9 . . 113.21(14) ? N1 C8 H8A . . 108.9 ? C9 C8 H8A . . 108.9 ? N1 C8 H8B . . 108.9 ? C9 C8 H8B . . 108.9 ? H8A C8 H8B . . 107.7 ? O2 C9 C8 . . 114.28(15) ? O2 C9 H9A . . 108.7 ? C8 C9 H9A . . 108.7 ? O2 C9 H9B . . 108.7 ? C8 C9 H9B . . 108.7 ? H9A C9 H9B . . 107.6 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 O2 1_655 2.5207(15) ? Cu1 O1 3_665 1.9540(13) yes Cu1 O1 . 1.9540(13) yes Cu1 N1 3_665 1.9961(15) yes Cu1 N1 . 1.9961(15) yes Cl1 C4 . 1.752(2) ? O1 C1 . 1.315(2) ? O2 C9 . 1.416(2) ? O2 H2 . 0.81(3) ? N1 C7 . 1.281(2) ? N1 C8 . 1.474(2) ? C1 C2 . 1.413(3) ? C1 C6 . 1.419(3) ? C2 C3 . 1.383(3) ? C2 H2A . 0.9500 ? C3 C4 . 1.388(3) ? C3 H3 . 0.9500 ? C4 C5 . 1.378(3) ? C5 C6 . 1.403(3) ? C5 H5 . 0.9500 ? C6 C7 . 1.450(2) ? C7 H7 . 0.9500 ? C8 C9 . 1.521(2) ? C8 H8A . 0.9900 ? C8 H8B . 0.9900 ? C9 H9A . 0.9900 ? C9 H9B . 0.9900 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C7 H7 Cl1 4_575 0.95 2.89 3.8144(19) 165 C8 H8A Cl1 1_554 0.99 2.86 3.446(2) 119 O2 H2 O1 3_665 0.81(3) 1.87(3) 2.658(2) 167(3) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion N1 Cu1 O1 C1 3_665 -134.30(14) N1 Cu1 O1 C1 . 45.70(14) O1 Cu1 N1 C7 3_665 148.38(14) O1 Cu1 N1 C7 . -31.62(14) O1 Cu1 N1 C8 3_665 -28.44(13) O1 Cu1 N1 C8 . 151.56(13) Cu1 O1 C1 C2 . 145.69(14) Cu1 O1 C1 C6 . -35.7(2) O1 C1 C2 C3 . -179.11(17) C6 C1 C2 C3 . 2.2(3) C1 C2 C3 C4 . -1.4(3) C2 C3 C4 C5 . -0.7(3) C2 C3 C4 Cl1 . 178.81(14) C3 C4 C5 C6 . 1.9(3) Cl1 C4 C5 C6 . -177.65(14) C4 C5 C6 C1 . -1.0(3) C4 C5 C6 C7 . -178.44(16) O1 C1 C6 C5 . -179.68(16) C2 C1 C6 C5 . -1.0(3) O1 C1 C6 C7 . -2.3(3) C2 C1 C6 C7 . 176.32(16) C8 N1 C7 C6 . -175.52(16) Cu1 N1 C7 C6 . 7.5(2) C5 C6 C7 N1 . -164.89(17) C1 C6 C7 N1 . 17.7(3) C7 N1 C8 C9 . -78.1(2) Cu1 N1 C8 C9 . 98.87(16) N1 C8 C9 O2 . -61.4(2)