#------------------------------------------------------------------------------ #$Date: 2016-02-19 22:18:51 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176760 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/29/2012998.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_2012998 loop_ _publ_author_name 'Okabe, Nobuo' 'Muranishi, Yasunori' 'Wada, Yoshio' _publ_section_title ; 5-n-Butylpyridine-2-carboxylate--copper(II) and --iron(III) complexes ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first m511 _journal_page_last m513 _journal_paper_doi 10.1107/S0108270102015615 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac '[Cu (C10 H12 N O2)2 (C H4 O)2]' _chemical_formula_moiety 'C22 H32 Cu N2 O6' _chemical_formula_sum 'C22 H32 Cu N2 O6' _chemical_formula_weight 484.05 _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' _cell_angle_alpha 90 _cell_angle_beta 99.88(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.462(4) _cell_length_b 6.612(4) _cell_length_c 21.456(3) _cell_measurement_reflns_used 23 _cell_measurement_temperature 296.2 _cell_measurement_theta_max 15.0 _cell_measurement_theta_min 14.9 _cell_volume 1182.7(9) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation and Rigaku Corporation, 2000) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation and Rigaku Corporation, 2000)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material TEXSAN _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR88 (Burla et al., 1989) and DIRDIF94 (Beurskens et al., 1994)' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Rigaku AFC-5R' _diffrn_measurement_method \w/2\q _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 3139 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.50 _diffrn_standards_decay_% 20.16 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.962 _exptl_absorpt_correction_T_max 0.825 _exptl_absorpt_correction_T_min 0.636 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 510.0 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.34 _refine_diff_density_min -0.77 _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.222 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 145 _refine_ls_number_reflns 2707 _refine_ls_R_factor_gt 0.045 _refine_ls_shift/su_max <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.166 _reflns_number_gt 1998 _reflns_number_total 2707 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob1079.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2012998 _cod_database_fobs_code 2012998 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cu1 1.0000 0.5000 1.0000 0.0504(2) Uani d S 1.00 . . Cu O1 1.2595(3) 0.9717(3) 0.9689(2) 0.0656(7) Uani d . 1.00 . . O O2 1.0586(2) 0.7512(3) 0.96190(10) 0.0557(6) Uani d . 1.00 . . O O3M 0.9219(3) 0.7222(3) 1.0898(2) 0.0718(7) Uani d . 1.00 . . O N1 1.2271(3) 0.5014(3) 1.04190(10) 0.0433(5) Uani d . 1.00 . . N C2 1.3026(3) 0.6691(4) 1.02720(10) 0.0428(6) Uani d . 1.00 . . C C3 1.4620(3) 0.7025(4) 1.0516(2) 0.0508(7) Uani d . 1.00 . . C C4 1.5427(3) 0.5608(5) 1.0924(2) 0.0533(7) Uani d . 1.00 . . C C5 1.4660(3) 0.3876(5) 1.1084(2) 0.0505(7) Uani d . 1.00 . . C C6 1.3051(3) 0.3657(4) 1.0814(2) 0.0493(7) Uani d . 1.00 . . C C7 1.2004(3) 0.8104(4) 0.9825(2) 0.0480(6) Uani d . 1.00 . . C C8 1.5542(4) 0.2338(6) 1.1530(2) 0.0704(10) Uani d . 1.00 . . C C9 1.4605(4) 0.0864(6) 1.1833(2) 0.0639(8) Uani d . 1.00 . . C C10 1.5649(5) -0.0517(7) 1.2296(2) 0.0790(10) Uani d . 1.00 . . C C11 1.4681(7) -0.2034(9) 1.2602(4) 0.128(2) Uani d . 1.00 . . C C12 1.0385(6) 0.8093(7) 1.1356(2) 0.0900(10) Uani d . 1.00 . . C H3 1.5140 0.8178 1.0408 0.0610 Uiso calc . 1.00 . . H H3M 0.8771 0.8108 1.0664 0.1078 Uiso calc . 1.00 . . H H4 1.6501 0.5817 1.1094 0.0640 Uiso calc . 1.00 . . H H6 1.2501 0.2518 1.0914 0.0592 Uiso calc . 1.00 . . H H8A 1.6237 0.1581 1.1300 0.0845 Uiso calc . 1.00 . . H H8B 1.6230 0.3068 1.1864 0.0845 Uiso calc . 1.00 . . H H9A 1.3967 0.0046 1.1508 0.0767 Uiso calc . 1.00 . . H H9B 1.3874 0.1590 1.2055 0.0767 Uiso calc . 1.00 . . H H10A 1.6385 -0.1237 1.2076 0.0945 Uiso calc . 1.00 . . H H10B 1.6281 0.0298 1.2624 0.0945 Uiso calc . 1.00 . . H H11A 1.3902 -0.1334 1.2798 0.1917 Uiso calc . 1.00 . . H H11B 1.5385 -0.2790 1.2916 0.1917 Uiso calc . 1.00 . . H H11C 1.4144 -0.2941 1.2285 0.1917 Uiso calc . 1.00 . . H H12A 1.0898 0.9180 1.1171 0.1355 Uiso calc . 1.00 . . H H12B 1.1170 0.7092 1.1519 0.1355 Uiso calc . 1.00 . . H H12C 0.9891 0.8609 1.1695 0.1355 Uiso calc . 1.00 . . 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 0.0314(3) 0.0423(3) 0.0728(4) -0.0144(2) -0.0046(2) 0.0189(2) O1 0.0450(10) 0.0410(10) 0.110(2) -0.0130(9) 0.0090(10) 0.0210(10) O2 0.0363(9) 0.0450(10) 0.082(2) -0.0116(8) -0.0015(9) 0.0185(10) O3M 0.0600(10) 0.0510(10) 0.102(2) -0.0060(10) 0.0050(10) 0.0080(10) N1 0.0320(10) 0.0400(10) 0.0560(10) -0.0106(8) 0.0022(9) 0.0049(9) C2 0.0340(10) 0.0350(10) 0.060(2) -0.0096(10) 0.0100(10) -0.0030(10) C3 0.0370(10) 0.0450(10) 0.070(2) -0.0170(10) 0.0090(10) -0.0020(10) C4 0.0310(10) 0.057(2) 0.069(2) -0.0140(10) -0.0010(10) -0.0010(10) C5 0.0350(10) 0.054(2) 0.060(2) -0.0060(10) 0.0020(10) 0.0040(10) C6 0.0370(10) 0.0440(10) 0.066(2) -0.0100(10) 0.0040(10) 0.0080(10) C7 0.0370(10) 0.0350(10) 0.072(2) -0.0080(10) 0.0120(10) 0.0040(10) C8 0.0380(10) 0.081(2) 0.087(3) -0.003(2) -0.004(2) 0.023(2) C9 0.051(2) 0.065(2) 0.073(2) 0.005(2) 0.002(2) 0.013(2) C10 0.065(2) 0.078(2) 0.087(3) 0.004(2) -0.005(2) 0.027(2) C11 0.108(4) 0.108(4) 0.158(5) -0.014(3) -0.004(4) 0.065(4) C12 0.094(3) 0.086(3) 0.086(3) -0.002(2) 0.000(2) -0.011(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cu Cu 0.320 1.265 ;International Tables for Crystallography (1992, 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 O2 Cu1 O2 . 3_767 180.0 no O2 Cu1 O3M . . 86.80(9) yes O2 Cu1 O3M . 3_767 93.20(9) no O2 Cu1 N1 . . 83.66(9) yes O2 Cu1 N1 . 3_767 96.34(9) no O2 Cu1 O3M 3_767 . 93.20(9) no O2 Cu1 O3M 3_767 3_767 86.80(9) no O2 Cu1 N1 3_767 . 96.34(9) no O2 Cu1 N1 3_767 3_767 83.66(9) no O3M Cu1 O3M . 3_767 180.0 no O3M Cu1 N1 . . 90.65(9) yes O3M Cu1 N1 . 3_767 89.35(9) no O3M Cu1 N1 3_767 . 89.35(9) no O3M Cu1 N1 3_767 3_767 90.65(9) no N1 Cu1 N1 . 3_767 180.0 no Cu1 O2 C7 . . 114.2(2) yes Cu1 O3M C12 . . 121.2(3) yes Cu1 O3M H3M . . 95.8 no C12 O3M H3M . . 109.5 no Cu1 N1 C2 . . 111.2(2) yes Cu1 N1 C6 . . 128.6(2) yes C2 N1 C6 . . 120.2(2) no N1 C2 C3 . . 121.1(2) no N1 C2 C7 . . 114.7(2) no C3 C2 C7 . . 124.2(2) no C2 C3 C4 . . 118.5(3) no C2 C3 H3 . . 120.7 no C4 C3 H3 . . 120.7 no C3 C4 C5 . . 121.0(3) no C3 C4 H4 . . 119.5 no C5 C4 H4 . . 119.5 no C4 C5 C6 . . 116.7(3) no C4 C5 C8 . . 120.8(3) no C6 C5 C8 . . 122.5(3) no N1 C6 C5 . . 122.5(3) no N1 C6 H6 . . 118.7 no C5 C6 H6 . . 118.7 no O1 C7 O2 . . 125.6(3) no O1 C7 C2 . . 118.5(2) no O2 C7 C2 . . 116.0(2) no C5 C8 C9 . . 118.8(3) no C5 C8 H8A . . 107.6 no C5 C8 H8B . . 107.6 no C9 C8 H8A . . 107.6 no C9 C8 H8B . . 107.6 no H8A C8 H8B . . 107.1 no C8 C9 C10 . . 113.0(3) no C8 C9 H9A . . 109.0 no C8 C9 H9B . . 109.0 no C10 C9 H9A . . 109.0 no C10 C9 H9B . . 109.0 no H9A C9 H9B . . 107.8 no C9 C10 C11 . . 112.7(4) no C9 C10 H10A . . 109.1 no C9 C10 H10B . . 109.1 no C11 C10 H10A . . 109.1 no C11 C10 H10B . . 109.1 no H10A C10 H10B . . 107.8 no C10 C11 H11A . . 109.5 no C10 C11 H11B . . 109.5 no C10 C11 H11C . . 109.5 no H11A C11 H11B . . 109.5 no H11A C11 H11C . . 109.5 no H11B C11 H11C . . 109.5 no O3M C12 H12A . . 109.5 no O3M C12 H12B . . 109.5 no O3M C12 H12C . . 109.5 no H12A C12 H12B . . 109.5 no H12A C12 H12C . . 109.5 no H12B C12 H12C . . 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 O2 . . 1.952(2) yes Cu1 O2 . 3_767 1.952(2) no Cu1 O3M . . 2.596(3) yes Cu1 O3M . 3_767 2.596(3) no Cu1 N1 . . 1.977(2) yes Cu1 N1 . 3_767 1.977(2) no O1 C7 . . 1.234(4) yes O2 C7 . . 1.268(3) yes O3M C12 . . 1.393(5) no O3M H3M . . 0.820 no N1 C2 . . 1.344(3) no N1 C6 . . 1.329(4) no C2 C3 . . 1.378(4) no C2 C7 . . 1.502(4) no C3 C4 . . 1.380(4) no C3 H3 . . 0.930 no C4 C5 . . 1.388(4) no C4 H4 . . 0.930 no C5 C6 . . 1.392(4) no C5 C8 . . 1.504(5) no C6 H6 . . 0.930 no C8 C9 . . 1.477(6) no C8 H8A . . 0.970 no C8 H8B . . 0.970 no C9 C10 . . 1.516(6) no C9 H9A . . 0.970 no C9 H9B . . 0.970 no C10 C11 . . 1.513(8) no C10 H10A . . 0.970 no C10 H10B . . 0.970 no C11 H11A . . 0.960 no C11 H11B . . 0.960 no C11 H11C . . 0.960 no C12 H12A . . 0.960 no C12 H12B . . 0.960 no C12 H12C . . 0.960 no 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 O3M H3M O1 3_777 0.82 1.92 2.716(4) 164.0 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Cu1 O2 C7 O1 . . . -174.4(3) no Cu1 O2 C7 C2 . . . 5.7(4) no Cu1 O2 C7 O1 3_767 3_767 3_767 174.4(3) no Cu1 O2 C7 C2 3_767 3_767 3_767 -5.7(4) no Cu1 N1 C2 C3 . . . 179.6(2) no Cu1 N1 C2 C7 . . . -1.2(3) no Cu1 N1 C6 C5 . . . -179.0(2) no Cu1 N1 C2 C3 3_767 3_767 3_767 -179.6(2) no Cu1 N1 C2 C7 3_767 3_767 3_767 1.2(3) no Cu1 N1 C6 C5 3_767 3_767 3_767 179.0(2) no O1 C7 C2 N1 . . . 177.1(3) no O1 C7 C2 C3 . . . -3.8(5) no O2 Cu1 O3M C12 . . . -74.6(3) no O2 Cu1 O3M C12 . 3_767 3_767 -105.4(3) no O2 Cu1 N1 C2 . . . 3.2(2) no O2 Cu1 N1 C6 . . . -178.6(3) no O2 Cu1 N1 C2 . 3_767 3_767 176.8(2) no O2 Cu1 N1 C6 . 3_767 3_767 -1.4(3) no O2 C7 C2 N1 . . . -3.0(4) no O2 C7 C2 C3 . . . 176.2(3) no O3M Cu1 O2 C7 . . . 85.9(2) no O3M Cu1 O2 C7 . 3_767 3_767 94.1(2) no O3M Cu1 N1 C2 . . . -83.5(2) no O3M Cu1 N1 C6 . . . 94.7(3) no O3M Cu1 N1 C2 . 3_767 3_767 -96.5(2) no O3M Cu1 N1 C6 . 3_767 3_767 85.3(3) no N1 Cu1 O2 C7 . . . -5.1(2) no N1 Cu1 O2 C7 . 3_767 3_767 -174.9(2) no N1 Cu1 O3M C12 . . . 9.0(3) no N1 Cu1 O3M C12 . 3_767 3_767 171.0(3) no N1 C2 C3 C4 . . . -1.0(5) no N1 C6 C5 C4 . . . 0.5(5) no N1 C6 C5 C8 . . . -179.9(3) no C2 N1 C6 C5 . . . -1.0(5) no C2 C3 C4 C5 . . . 0.4(5) no C3 C2 N1 C6 . . . 1.2(4) no C3 C4 C5 C6 . . . -0.2(5) no C3 C4 C5 C8 . . . -179.8(3) no C4 C3 C2 C7 . . . 179.9(3) no C4 C5 C8 C9 . . . 162.1(3) no C5 C8 C9 C10 . . . -177.0(3) no C6 N1 C2 C7 . . . -179.5(3) no C6 C5 C8 C9 . . . -17.5(5) no C8 C9 C10 C11 . . . -179.6(4) no