#------------------------------------------------------------------------------ #$Date: 2014-03-11 16:41:00 +0000 (Tue, 11 Mar 2014) $ #$Revision: 104950 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/90/2239073.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_2239073 loop_ _publ_author_name 'Chygorin, Eduard N.' 'Smal, Yuri O.' 'Kokozay, Vladimir N.' 'Omelchenko, Irina V.' _publ_section_title ; Tetrakis(\m~3~-2-{[1,1-bis(hydroxymethyl)-2-oxidoethyl]iminomethyl}-6-nitrophenolato)tetracopper(II) ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first m54 _journal_page_last m55 _journal_paper_doi 10.1107/S1600536814000798 _journal_volume 70 _journal_year 2014 _chemical_formula_iupac '[Cu4 (C11 H12 N2 O6)4]' _chemical_formula_moiety 'C44 H48 Cu4 N8 O24' _chemical_formula_sum 'C44 H48 Cu4 N8 O24' _chemical_formula_weight 1327.06 _chemical_name_systematic Tetrakis(\m~3~-2-{[1,1-bis(hydroxymethyl)-2-oxidoethyl]iminomethyl}-6-nitrophenolato)tetracopper(II) _space_group_IT_number 88 _symmetry_cell_setting tetragonal _symmetry_space_group_name_Hall '-I 4ad' _symmetry_space_group_name_H-M 'I 41/a :2' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 20.5587(14) _cell_length_b 20.5587(14) _cell_length_c 18.010(2) _cell_measurement_reflns_used 462 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.0 _cell_measurement_theta_min 3.0 _cell_volume 7612.1(11) _computing_cell_refinement 'CrysAlis RED (Agilent, 2012)' _computing_data_collection 'CrysAlis CCD (Agilent, 2012)' _computing_data_reduction 'CrysAlis RED (Agilent, 2012)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'publCIF (Westrip, 2010)' _computing_structure_refinement 'OLEX2 (Dolomanov et al., 2009)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _diffrn_ambient_temperature 173(2) _diffrn_detector_area_resol_mean 16.1827 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Agilent Xcalibur Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.2287 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3349 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 3.18 _diffrn_standards_decay_% 1 _diffrn_standards_interval_count 50 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 1.166 _exptl_absorpt_correction_T_max 0.7211 _exptl_absorpt_correction_T_min 0.6527 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrysAlis PRO; Agilent, 2012)' _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2704 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _platon_squeeze_details ; ; _refine_diff_density_max 0.941 _refine_diff_density_min -0.573 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.801 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 3349 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.801 _refine_ls_R_factor_all 0.1551 _refine_ls_R_factor_gt 0.0752 _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^)+(0.0600P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1563 _refine_ls_wR_factor_ref 0.1844 _reflns_number_gt 1395 _reflns_number_total 3349 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hb7174sup1.cf _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'I 41/a' _cod_original_cell_volume 7612.0(11) _cod_database_code 2239073 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' loop_ _atom_site_type_symbol _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_symmetry_multiplicity Cu Cu1 0.48941(4) 0.66864(4) 0.06731(4) 0.0396(3) Uani d . 1 1 O O1 0.5536(2) 0.6041(2) 0.0524(3) 0.0451(13) Uani d . 1 1 N N1 0.4460(3) 0.6539(3) -0.0276(3) 0.0406(16) Uani d . 1 1 C C1 0.5204(4) 0.5693(4) -0.0716(4) 0.047(2) Uani d . 1 1 N N2 0.6541(4) 0.5153(3) 0.0538(4) 0.0542(19) Uani d . 1 1 O O2 0.6303(3) 0.5101(3) 0.1159(3) 0.0611(17) Uani d . 1 1 C C2 0.5608(4) 0.5690(4) -0.0063(5) 0.047(2) Uani d . 1 1 O O3 0.7144(3) 0.5100(3) 0.0436(3) 0.0751(19) Uani d . 1 1 C C3 0.6141(4) 0.5230(4) -0.0096(5) 0.050(2) Uani d . 1 1 O O4 0.4358(3) 0.7332(3) -0.1606(3) 0.0761(19) Uani d . 1 1 H H4A 0.4728 0.7401 -0.1646 0.114 Uiso d PR 0.50 1 H H4C 0.4145 0.7014 -0.1769 0.114 Uiso d PR 0.50 1 C C4 0.6276(4) 0.4875(4) -0.0723(5) 0.061(2) Uani d . 1 1 H H4B 0.6644 0.4596 -0.0728 0.073 Uiso calc R 1 1 O O5 0.2776(3) 0.7029(3) -0.0736(4) 0.0732(18) Uani d . 1 1 H H5A 0.2430 0.6816 -0.0784 0.110 Uiso calc R 1 1 C C5 0.5890(4) 0.4913(4) -0.1342(5) 0.061(3) Uani d . 1 1 H H5B 0.5991 0.4672 -0.1777 0.073 Uiso calc R 1 1 O O6 0.4282(2) 0.7408(2) 0.0779(2) 0.0369(12) Uani d . 1 1 C C6 0.5353(4) 0.5310(4) -0.1317(4) 0.052(2) Uani d . 1 1 H H6A 0.5071 0.5320 -0.1735 0.063 Uiso calc R 1 1 C C7 0.4659(4) 0.6122(4) -0.0773(4) 0.048(2) Uani d . 1 1 H H7A 0.4416 0.6101 -0.1220 0.057 Uiso calc R 1 1 C C8 0.3906(4) 0.6972(4) -0.0412(4) 0.047(2) Uani d . 1 1 C C9 0.4121(4) 0.7530(4) -0.0911(4) 0.057(2) Uani d . 1 1 H H9A 0.3747 0.7826 -0.0989 0.069 Uiso calc R 1 1 H H9B 0.4465 0.7780 -0.0653 0.069 Uiso calc R 1 1 C C10 0.3319(4) 0.6594(4) -0.0737(5) 0.058(2) Uani d . 1 1 H H10A 0.3415 0.6448 -0.1249 0.069 Uiso calc R 1 1 H H10B 0.3223 0.6206 -0.0430 0.069 Uiso calc R 1 1 C C11 0.3712(4) 0.7262(4) 0.0359(4) 0.0436(19) Uani d . 1 1 H H11A 0.3454 0.7663 0.0285 0.052 Uiso calc R 1 1 H H11B 0.3440 0.6945 0.0633 0.052 Uiso calc R 1 1 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 0.0337(6) 0.0344(6) 0.0509(5) 0.0009(5) -0.0021(5) -0.0018(4) O1 0.044(3) 0.029(3) 0.062(3) -0.005(3) -0.002(3) -0.015(3) N1 0.039(4) 0.037(4) 0.046(3) -0.005(3) -0.001(3) -0.006(3) C1 0.032(5) 0.046(5) 0.064(5) 0.001(4) 0.007(4) -0.004(5) N2 0.053(5) 0.038(4) 0.071(5) 0.012(4) -0.004(4) -0.017(4) O2 0.059(4) 0.040(4) 0.084(4) 0.008(3) -0.019(4) -0.004(3) C2 0.034(5) 0.022(4) 0.084(6) -0.001(4) 0.003(5) -0.009(4) O3 0.032(4) 0.077(5) 0.116(5) 0.013(3) -0.001(3) -0.026(4) C3 0.039(5) 0.041(5) 0.071(5) -0.023(4) -0.002(5) -0.018(5) O4 0.082(5) 0.088(5) 0.059(3) -0.014(4) 0.006(3) 0.006(3) C4 0.039(5) 0.045(6) 0.098(6) -0.004(5) 0.005(5) -0.024(5) O5 0.038(4) 0.065(4) 0.116(5) 0.001(3) -0.020(4) 0.000(4) C5 0.037(5) 0.051(6) 0.094(6) -0.004(5) 0.020(5) -0.033(5) O6 0.019(3) 0.029(3) 0.063(3) 0.002(2) -0.007(2) 0.004(2) C6 0.040(5) 0.054(6) 0.062(5) -0.012(5) 0.005(4) -0.016(5) C7 0.044(5) 0.048(5) 0.051(5) -0.013(4) -0.001(4) 0.010(4) C8 0.032(5) 0.043(5) 0.067(5) 0.005(4) -0.013(4) 0.004(4) C9 0.048(6) 0.063(6) 0.062(5) -0.010(5) -0.017(4) 0.010(5) C10 0.041(5) 0.061(6) 0.071(5) 0.005(5) 0.000(5) -0.007(5) C11 0.030(5) 0.041(5) 0.059(4) 0.000(4) 0.003(4) -0.002(4) 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' 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 O1 Cu1 O6 . 12_766 93.6(2) O1 Cu1 N1 . . 94.9(2) O6 Cu1 N1 12_766 . 164.4(2) O1 Cu1 O6 . . 174.8(2) O6 Cu1 O6 12_766 . 87.9(2) O1 Cu1 O6 . 6_564 93.45(18) O6 Cu1 O6 12_766 6_564 73.19(17) N1 Cu1 O6 . 6_564 119.2(2) O6 Cu1 O6 . 6_564 82.22(17) N1 Cu1 O6 . . 84.8(2) C2 O1 Cu1 . . 126.0(5) C7 N1 C8 . . 121.9(6) C7 N1 Cu1 . . 124.0(5) C8 N1 Cu1 . . 114.0(5) C6 C1 C7 . . 118.2(8) C6 C1 C2 . . 120.9(8) C7 C1 C2 . . 120.8(7) O2 N2 O3 . . 121.3(7) O2 N2 C3 . . 120.9(7) O3 N2 C3 . . 117.6(7) O1 C2 C1 . . 127.1(7) O1 C2 C3 . . 119.0(7) C1 C2 C3 . . 113.9(7) C4 C3 N2 . . 119.1(8) C4 C3 C2 . . 122.3(8) N2 C3 C2 . . 118.6(7) C9 O4 H4A . . 111.7 C9 O4 H4C . . 110.9 H4A O4 H4C . . 128.4 C5 C4 C3 . . 121.4(8) C5 C4 H4B . . 119.3 C3 C4 H4B . . 119.3 C10 O5 H5A . . 109.5 C4 C5 C6 . . 118.2(8) C4 C5 H5B . . 120.9 C6 C5 H5B . . 120.9 C11 O6 Cu1 . 15_565 118.5(4) C11 O6 Cu1 . . 108.5(4) Cu1 O6 Cu1 15_565 . 108.6(2) C1 C6 C5 . . 123.1(8) C1 C6 H6A . . 118.5 C5 C6 H6A . . 118.5 N1 C7 C1 . . 127.0(7) N1 C7 H7A . . 116.5 C1 C7 H7A . . 116.5 N1 C8 C9 . . 109.3(6) N1 C8 C10 . . 111.3(6) C9 C8 C10 . . 112.3(6) N1 C8 C11 . . 106.4(6) C9 C8 C11 . . 108.1(7) C10 C8 C11 . . 109.2(6) O4 C9 C8 . . 114.1(7) O4 C9 H9A . . 108.7 C8 C9 H9A . . 108.7 O4 C9 H9B . . 108.7 C8 C9 H9B . . 108.7 H9A C9 H9B . . 107.6 O5 C10 C8 . . 107.0(6) O5 C10 H10A . . 110.3 C8 C10 H10A . . 110.3 O5 C10 H10B . . 110.3 C8 C10 H10B . . 110.3 H10A C10 H10B . . 108.6 O6 C11 C8 . . 110.0(6) O6 C11 H11A . . 109.7 C8 C11 H11A . . 109.7 O6 C11 H11B . . 109.7 C8 C11 H11B . . 109.7 H11A C11 H11B . . 108.2 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 O1 . 1.892(5) y Cu1 O6 12_766 1.940(5) y Cu1 N1 . 1.952(6) y Cu1 O6 . 1.954(4) y Cu1 O6 6_564 2.524(5) y O1 C2 . 1.288(8) ? N1 C7 . 1.304(9) ? N1 C8 . 1.467(9) ? C1 C6 . 1.373(10) ? C1 C7 . 1.428(10) ? C1 C2 . 1.440(10) ? N2 O2 . 1.224(8) ? N2 O3 . 1.259(8) ? N2 C3 . 1.417(10) ? C2 C3 . 1.449(10) ? C3 C4 . 1.373(10) ? O4 C9 . 1.403(9) ? O4 H4A . 0.7773 ? O4 H4C . 0.8400 ? C4 C5 . 1.371(11) ? C4 H4B . 0.9500 ? O5 C10 . 1.430(9) ? O5 H5A . 0.8400 ? C5 C6 . 1.374(11) ? C5 H5B . 0.9500 ? O6 C11 . 1.428(8) ? O6 Cu1 15_565 1.940(5) ? C6 H6A . 0.9500 ? C7 H7A . 0.9500 ? C8 C9 . 1.524(10) ? C8 C10 . 1.551(10) ? C8 C11 . 1.562(10) ? C9 H9A . 0.9900 ? C9 H9B . 0.9900 ? C10 H10A . 0.9900 ? C10 H10B . 0.9900 ? C11 H11A . 0.9900 ? C11 H11B . 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 O4 H4A O4 6_564 0.78 1.96 2.729(9) 171 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_site_symmetry_4 _geom_torsion O6 Cu1 O1 C2 12_766 . 170.0(6) N1 Cu1 O1 C2 . . 3.0(6) O6 Cu1 O1 C2 . . -84(2) O6 Cu1 O1 C2 6_564 . -116.7(6) O1 Cu1 N1 C7 . . -2.5(6) O6 Cu1 N1 C7 12_766 . -125.4(8) O6 Cu1 N1 C7 . . 172.3(6) O6 Cu1 N1 C7 6_564 . 94.2(6) O1 Cu1 N1 C8 . . -178.6(5) O6 Cu1 N1 C8 12_766 . 58.5(11) O6 Cu1 N1 C8 . . -3.8(5) O6 Cu1 N1 C8 6_564 . -81.9(5) Cu1 O1 C2 C1 . . -2.8(11) Cu1 O1 C2 C3 . . 178.0(5) C6 C1 C2 O1 . . 177.4(7) C7 C1 C2 O1 . . 1.0(12) C6 C1 C2 C3 . . -3.4(11) C7 C1 C2 C3 . . -179.7(7) O2 N2 C3 C4 . . -135.5(8) O3 N2 C3 C4 . . 40.2(11) O2 N2 C3 C2 . . 45.5(10) O3 N2 C3 C2 . . -138.8(8) O1 C2 C3 C4 . . -175.1(7) C1 C2 C3 C4 . . 5.5(11) O1 C2 C3 N2 . . 3.8(11) C1 C2 C3 N2 . . -175.5(7) N2 C3 C4 C5 . . 177.6(8) C2 C3 C4 C5 . . -3.5(13) C3 C4 C5 C6 . . -1.2(13) O1 Cu1 O6 C11 . . 114(2) O6 Cu1 O6 C11 12_766 . -139.6(4) N1 Cu1 O6 C11 . . 26.7(4) O1 Cu1 O6 Cu1 . 15_565 -116(2) O6 Cu1 O6 Cu1 12_766 15_565 -9.5(2) N1 Cu1 O6 Cu1 . 15_565 156.7(3) C7 C1 C6 C5 . . 175.5(7) C2 C1 C6 C5 . . -0.9(12) C4 C5 C6 C1 . . 3.4(13) C8 N1 C7 C1 . . 177.6(7) Cu1 N1 C7 C1 . . 1.8(11) C6 C1 C7 N1 . . -177.0(7) C2 C1 C7 N1 . . -0.6(12) C7 N1 C8 C9 . . -77.3(8) Cu1 N1 C8 C9 . . 98.9(6) C7 N1 C8 C10 . . 47.3(9) Cu1 N1 C8 C10 . . -136.5(5) C7 N1 C8 C11 . . 166.2(6) Cu1 N1 C8 C11 . . -17.6(7) N1 C8 C9 O4 . . 59.8(8) C10 C8 C9 O4 . . -64.2(9) C11 C8 C9 O4 . . 175.3(6) N1 C8 C10 O5 . . 170.8(6) C9 C8 C10 O5 . . -66.3(8) C11 C8 C10 O5 . . 53.6(8) Cu1 O6 C11 C8 15_565 . -167.6(4) Cu1 O6 C11 C8 . . -43.2(6) N1 C8 C11 O6 . . 39.5(8) C9 C8 C11 O6 . . -77.8(7) C10 C8 C11 O6 . . 159.8(6) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.007 -0.005 -0.006 3131 749 ' ' _cod_database_fobs_code 2239073