#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202268.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_2202268 loop_ _publ_author_name 'Reinoso, Santiago' 'Vitoria, Pablo' 'San Felices, Leire' 'Lezama, Luis' 'Guti\'errez-Zorrilla, Juan M.' _publ_section_title ; Bis(di-2-pyridylmethanediol-\k^3^N,O,N')copper(II) diacetate tetrahydrate ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first m548 _journal_page_last m550 _journal_paper_doi 10.1107/S1600536803014399 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac '[Cu (C11 H10 N2 O2)2] (C2 H3 O2)2, 4H2 O' _chemical_formula_moiety 'C22 H20 Cu N4 O4, 2(C2 H3 O2), 4(H2 O)' _chemical_formula_sum 'C26 H34 Cu N4 O12' _chemical_formula_weight 658.11 _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_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 98.000(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.6170(10) _cell_length_b 7.8765(9) _cell_length_c 23.103(3) _cell_measurement_reflns_used 6500 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25 _cell_measurement_theta_min 3.5 _cell_volume 1552.8(3) _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2002)' _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2002)' _computing_data_reduction CrysAlisRED _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'DIRDIF99.2 (Beurskens et al., 1999)' _diffrn_detector_area_resol_mean '1024 \\times 1024 with blocks 2 \\times 2' _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type Xcalibur _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0573 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 12971 _diffrn_reflns_theta_full 30 _diffrn_reflns_theta_max 30 _diffrn_reflns_theta_min 3.52 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.769 _exptl_absorpt_correction_T_max 0.931 _exptl_absorpt_correction_T_min 0.793 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(CrysAlisRED; Oxford Diffraction, 2002)' _exptl_crystal_colour purple _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 686 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.470 _refine_diff_density_min -0.343 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 4480 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 0.954 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0490 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0588P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1035 _refine_ls_wR_factor_ref 0.1150 _reflns_number_gt 2765 _reflns_number_total 4484 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ac6048.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2202268 _cod_database_fobs_code 2202268 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cu1 0.0000 0.0000 0.0000 0.03418(12) Uani d S 1 . . Cu O14 -0.03830(18) 0.26003(18) -0.05417(6) 0.0367(3) Uani d . 1 . . O H14 -0.0435 0.2576 -0.0899 0.055 Uiso calc R 1 . . H O15 -0.2598(2) 0.43429(19) -0.06184(7) 0.0479(4) Uani d . 1 . . O H15 -0.2623 0.4341 -0.0975 0.072 Uiso calc R 1 . . H N1 -0.2177(2) -0.0169(2) -0.04184(7) 0.0342(4) Uani d . 1 . . N N13 -0.0808(2) 0.1706(2) 0.05422(7) 0.0362(4) Uani d . 1 . . N C2 -0.2932(3) -0.1636(3) -0.05549(11) 0.0448(6) Uani d . 1 . . C H2 -0.2429 -0.2654 -0.0445 0.054 Uiso calc R 1 . . H C3 -0.4424(3) -0.1677(3) -0.08517(13) 0.0568(7) Uani d . 1 . . C H3 -0.4919 -0.2708 -0.0949 0.068 Uiso calc R 1 . . H C4 -0.5179(3) -0.0169(3) -0.10027(13) 0.0607(7) Uani d . 1 . . C H4 -0.6198 -0.0171 -0.1198 0.073 Uiso calc R 1 . . H C5 -0.4416(3) 0.1343(3) -0.08622(11) 0.0479(6) Uani d . 1 . . C H5 -0.4909 0.2372 -0.0964 0.058 Uiso calc R 1 . . H C6 -0.2907(2) 0.1307(3) -0.05680(9) 0.0339(5) Uani d . 1 . . C C7 -0.1888(3) 0.2873(2) -0.03881(9) 0.0352(5) Uani d . 1 . . C C8 -0.1650(2) 0.2981(2) 0.02719(10) 0.0356(5) Uani d . 1 . . C C9 -0.2239(3) 0.4264(3) 0.05854(11) 0.0462(6) Uani d . 1 . . C H9 -0.2825 0.5141 0.0394 0.055 Uiso calc R 1 . . H C10 -0.1942(3) 0.4222(3) 0.11879(12) 0.0547(7) Uani d . 1 . . C H10 -0.2319 0.5080 0.1407 0.066 Uiso calc R 1 . . H C11 -0.1092(3) 0.2917(3) 0.14599(11) 0.0563(7) Uani d . 1 . . C H11 -0.0891 0.2868 0.1866 0.068 Uiso calc R 1 . . H C12 -0.0535(3) 0.1673(3) 0.11248(10) 0.0458(6) Uani d . 1 . . C H12 0.0047 0.0784 0.1310 0.055 Uiso calc R 1 . . H C20 -0.1655(3) 0.3480(3) -0.19680(11) 0.0532(7) Uani d . 1 . . C C21 -0.1604(5) 0.3642(5) -0.26154(13) 0.0883(11) Uani d . 1 . . C H21A -0.1804 0.2554 -0.2798 0.132 Uiso calc R 1 . . H H21B -0.0588 0.4037 -0.2679 0.132 Uiso calc R 1 . . H H21C -0.2387 0.4437 -0.2781 0.132 Uiso calc R 1 . . H O1 -0.0614(2) 0.2591(2) -0.16774(8) 0.0582(5) Uani d . 1 . . O O2 -0.2713(2) 0.4210(3) -0.17510(8) 0.0656(5) Uani d . 1 . . O O10 -0.5910(3) 0.3908(3) -0.21450(10) 0.0762(6) Uani d D 1 . . O O11 0.2041(3) 0.1290(3) -0.20391(11) 0.0742(6) Uani d D 1 . . O H10A -0.4931(14) 0.409(5) -0.2079(14) 0.089 Uiso d D 1 . . H H10B -0.619(4) 0.473(3) -0.2368(13) 0.089 Uiso d D 1 . . H H11A 0.124(3) 0.184(4) -0.1972(15) 0.089 Uiso d D 1 . . H H11B 0.263(3) 0.210(3) -0.2101(16) 0.089 Uiso d 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 0.0351(2) 0.03151(19) 0.0341(2) -0.00007(17) -0.00151(13) -0.00008(16) O14 0.0406(8) 0.0370(8) 0.0332(8) -0.0042(6) 0.0071(6) 0.0024(6) O15 0.0667(12) 0.0307(7) 0.0457(10) 0.0103(8) 0.0053(8) 0.0059(7) N1 0.0376(9) 0.0291(9) 0.0349(9) -0.0042(8) 0.0014(7) 0.0009(7) N13 0.0378(10) 0.0400(9) 0.0295(9) -0.0066(8) 0.0006(7) -0.0005(7) C2 0.0480(15) 0.0339(11) 0.0522(15) -0.0091(10) 0.0058(11) 0.0009(10) C3 0.0493(16) 0.0505(15) 0.0685(18) -0.0192(13) 0.0010(13) -0.0020(13) C4 0.0362(13) 0.0736(19) 0.0683(18) -0.0137(13) -0.0067(11) 0.0014(14) C5 0.0363(13) 0.0512(13) 0.0540(15) 0.0065(11) -0.0016(11) 0.0078(12) C6 0.0347(12) 0.0349(11) 0.0317(11) 0.0006(9) 0.0032(9) 0.0019(9) C7 0.0424(12) 0.0280(10) 0.0350(11) 0.0023(9) 0.0044(9) 0.0017(8) C8 0.0372(12) 0.0296(10) 0.0405(12) -0.0068(9) 0.0076(9) -0.0005(9) C9 0.0524(15) 0.0362(11) 0.0523(15) -0.0028(11) 0.0149(11) -0.0056(11) C10 0.0648(18) 0.0510(14) 0.0527(16) -0.0167(13) 0.0234(13) -0.0190(13) C11 0.0663(18) 0.0675(17) 0.0356(13) -0.0176(15) 0.0087(12) -0.0078(12) C12 0.0486(14) 0.0538(14) 0.0339(12) -0.0072(11) 0.0023(10) 0.0008(10) C20 0.0591(18) 0.0570(15) 0.0418(14) -0.0085(13) 0.0009(13) 0.0054(12) C21 0.109(3) 0.111(3) 0.0429(17) 0.022(2) 0.0045(17) 0.0133(17) O1 0.0571(11) 0.0771(12) 0.0400(10) 0.0093(10) 0.0057(8) 0.0055(9) O2 0.0598(12) 0.0834(13) 0.0515(11) 0.0163(11) 0.0007(9) 0.0118(10) O10 0.0565(13) 0.0928(16) 0.0798(16) 0.0000(13) 0.0111(12) 0.0166(12) O11 0.0554(14) 0.0713(14) 0.0963(16) 0.0008(10) 0.0124(12) -0.0062(12) 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 0 '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 0.006 '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' 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 N1 Cu1 N1 3 . 180.00(14) ? N1 Cu1 N13 3 3 87.86(7) y N1 Cu1 N13 . 3 92.14(7) ? N1 Cu1 N13 3 . 92.14(7) y N1 Cu1 N13 . . 87.86(7) y N13 Cu1 N13 3 . 180.00(11) ? N1 Cu1 O14 3 3 75.63(6) y N1 Cu1 O14 . 3 104.37(6) y N13 Cu1 O14 3 3 73.86(6) y N13 Cu1 O14 . 3 106.14(6) y C7 O14 H14 . . 109.5 ? C7 O15 H15 . . 109.5 ? C2 N1 C6 . . 119.38(18) ? C2 N1 Cu1 . . 124.37(15) y C6 N1 Cu1 . . 116.25(13) y C12 N13 C8 . . 119.5(2) ? C12 N13 Cu1 . . 125.69(16) y C8 N13 Cu1 . . 114.77(14) y N1 C2 C3 . . 121.9(2) ? N1 C2 H2 . . 119.1 ? C3 C2 H2 . . 119.1 ? C2 C3 C4 . . 118.9(2) ? C2 C3 H3 . . 120.5 ? C4 C3 H3 . . 120.5 ? C3 C4 C5 . . 119.6(2) ? C3 C4 H4 . . 120.2 ? C5 C4 H4 . . 120.2 ? C4 C5 C6 . . 119.0(2) ? C4 C5 H5 . . 120.5 ? C6 C5 H5 . . 120.5 ? N1 C6 C5 . . 121.25(19) ? N1 C6 C7 . . 113.31(18) ? C5 C6 C7 . . 125.43(19) ? O15 C7 O14 . . 113.88(17) ? O15 C7 C8 . . 109.37(17) ? O14 C7 C8 . . 105.19(17) ? O15 C7 C6 . . 111.29(17) ? O14 C7 C6 . . 108.72(16) ? C8 C7 C6 . . 108.08(16) ? N13 C8 C9 . . 121.2(2) ? N13 C8 C7 . . 114.58(18) ? C9 C8 C7 . . 124.2(2) ? C10 C9 C8 . . 118.8(2) ? C10 C9 H9 . . 120.6 ? C8 C9 H9 . . 120.6 ? C11 C10 C9 . . 119.7(2) ? C11 C10 H10 . . 120.2 ? C9 C10 H10 . . 120.2 ? C10 C11 C12 . . 119.0(2) ? C10 C11 H11 . . 120.5 ? C12 C11 H11 . . 120.5 ? N13 C12 C11 . . 121.8(2) ? N13 C12 H12 . . 119.1 ? C11 C12 H12 . . 119.1 ? O2 C20 O1 . . 123.5(2) ? O2 C20 C21 . . 119.1(3) ? O1 C20 C21 . . 117.4(3) ? C20 C21 H21A . . 109.5 ? C20 C21 H21B . . 109.5 ? H21A C21 H21B . . 109.5 ? C20 C21 H21C . . 109.5 ? H21A C21 H21C . . 109.5 ? H21B C21 H21C . . 109.5 ? H10A O10 H10B . . 100(3) ? H11A O11 H11B . . 100(3) ? 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 N1 3 1.9918(17) y Cu1 N1 . 1.9918(17) ? Cu1 N13 3 2.0257(18) y Cu1 N13 . 2.0257(18) ? Cu1 O14 3 2.3990(14) y O14 C7 . 1.408(3) y O14 H14 . 0.8200 ? O15 C7 . 1.381(2) y O15 H15 . 0.8200 ? N1 C2 . 1.342(3) ? N1 C6 . 1.344(3) ? N13 C12 . 1.334(3) ? N13 C8 . 1.341(3) ? C2 C3 . 1.371(3) ? C2 H2 . 0.9300 ? C3 C4 . 1.375(4) ? C3 H3 . 0.9300 ? C4 C5 . 1.377(3) ? C4 H4 . 0.9300 ? C5 C6 . 1.381(3) ? C5 H5 . 0.9300 ? C6 C7 . 1.537(3) ? C7 C8 . 1.512(3) ? C8 C9 . 1.381(3) ? C9 C10 . 1.380(4) ? C9 H9 . 0.9300 ? C10 C11 . 1.364(4) ? C10 H10 . 0.9300 ? C11 C12 . 1.376(4) ? C11 H11 . 0.9300 ? C12 H12 . 0.9300 ? C20 O2 . 1.240(3) ? C20 O1 . 1.257(3) ? C20 C21 . 1.508(4) ? C21 H21A . 0.9600 ? C21 H21B . 0.9600 ? C21 H21C . 0.9600 ? O10 H10A . 0.848(10) ? O10 H10B . 0.845(10) ? O11 H11A . 0.848(10) ? O11 H11B . 0.842(10) ? 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 O14 H14 O1 . 0.82 1.78 2.603(2) 178 O15 H15 O2 . 0.82 1.79 2.607(3) 177 O10 H10A O2 . 0.848(10) 1.958(13) 2.788(3) 166(3) O10 H10B O11 2_454 0.845(10) 1.906(12) 2.741(3) 169(3) O11 H11A O1 . 0.848(10) 1.915(14) 2.741(3) 164(3) O11 H11B O10 1_655 0.842(10) 1.910(11) 2.748(3) 173(4) 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 N13 Cu1 N1 C2 3 49.06(18) N13 Cu1 N1 C2 . -130.94(18) O14 Cu1 N1 C2 3 -24.82(19) N13 Cu1 N1 C6 3 -130.93(15) N13 Cu1 N1 C6 . 49.07(15) O14 Cu1 N1 C6 3 155.19(14) N1 Cu1 N13 C12 3 -49.05(18) N1 Cu1 N13 C12 . 130.95(18) O14 Cu1 N13 C12 3 26.61(19) N1 Cu1 N13 C8 3 129.10(15) N1 Cu1 N13 C8 . -50.90(15) O14 Cu1 N13 C8 3 -155.24(14) C6 N1 C2 C3 . 1.0(3) Cu1 N1 C2 C3 . -179.0(2) N1 C2 C3 C4 . -1.4(4) C2 C3 C4 C5 . 1.1(4) C3 C4 C5 C6 . -0.4(4) C2 N1 C6 C5 . -0.3(3) Cu1 N1 C6 C5 . 179.67(17) C2 N1 C6 C7 . -179.4(2) Cu1 N1 C6 C7 . 0.6(2) C4 C5 C6 N1 . 0.0(4) C4 C5 C6 C7 . 179.0(2) N1 C6 C7 O15 . 171.84(18) C5 C6 C7 O15 . -7.2(3) N1 C6 C7 O14 . 45.6(2) C5 C6 C7 O14 . -133.4(2) N1 C6 C7 C8 . -68.0(2) C5 C6 C7 C8 . 112.9(2) C12 N13 C8 C9 . 0.1(3) Cu1 N13 C8 C9 . -178.18(16) C12 N13 C8 C7 . -179.62(19) Cu1 N13 C8 C7 . 2.1(2) O15 C7 C8 N13 . -172.77(18) O14 C7 C8 N13 . -50.1(2) C6 C7 C8 N13 . 65.9(2) O15 C7 C8 C9 . 7.5(3) O14 C7 C8 C9 . 130.2(2) C6 C7 C8 C9 . -113.8(2) N13 C8 C9 C10 . 0.3(3) C7 C8 C9 C10 . 180.0(2) C8 C9 C10 C11 . -0.6(4) C9 C10 C11 C12 . 0.6(4) C8 N13 C12 C11 . -0.1(3) Cu1 N13 C12 C11 . 177.93(18) C10 C11 C12 N13 . -0.2(4)