#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/47/2204744.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_2204744
loop_
_publ_author_name
'Gao, Shan'
'Gu, Chang-Sheng'
'Huo, Li-Hua'
'Liu, Ji-Wei'
'Zhao, Jing-Gui'
_publ_section_title
;
 Bis(μ-3-carboxylatophenoxyacetato)bis[(1H-imidazole)copper(II)]
 dihydrate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1933
_journal_page_last               m1935
_journal_paper_doi               10.1107/S1600536804029976
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          '[Cu2 (C9 H6 O5)2 (C3 H4 N2)4], 2H2 O'
_chemical_formula_moiety         'C30 H28 Cu2 N8 O10, 2H2 O'
_chemical_formula_sum            'C30 H32 Cu2 N8 O12'
_chemical_formula_weight         823.74
_chemical_name_systematic
;
Bis(μ-3-carboxylatophenoxyacetato)bis[(1H-imidazole)copper(II)] dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.20(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.997(2)
_cell_length_b                   16.422(3)
_cell_length_c                   10.857(2)
_cell_measurement_reflns_used    15849
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.13
_cell_volume                     1764.2(6)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16077
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         3.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.278
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.282
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3982
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0382
_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/[σ²(Fo²)+(0.0558P)²+0.5757P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                3319
_reflns_number_total             3982
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6310.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204744
_cod_database_fobs_code          2204744
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.14180(3) 0.625677(16) 0.73660(2) 0.04230(11) Uani d . 1 Cu
N1 0.2031(2) 0.51828(12) 0.80959(19) 0.0506(4) Uani d . 1 N
N2 0.2494(2) 0.38832(13) 0.8197(2) 0.0621(6) Uani d . 1 N
N3 0.08196(19) 0.73278(11) 0.66421(18) 0.0468(4) Uani d . 1 N
N4 0.0060(2) 0.82315(13) 0.52347(19) 0.0580(5) Uani d . 1 N
O1 0.29451(16) 0.67706(10) 0.83965(14) 0.0506(4) Uani d . 1 O
O2 0.50898(17) 0.71365(11) 0.87529(17) 0.0615(5) Uani d . 1 O
O3 0.31831(17) 0.62502(10) 0.61070(16) 0.0541(4) Uani d . 1 O
O4 0.01582(15) 0.43002(9) 0.35865(14) 0.0464(3) Uani d . 1 O
O5 0.11393(18) 0.40470(11) 0.19206(16) 0.0574(4) Uani d . 1 O
O1W 0.2490(2) 0.24494(13) 0.6957(3) 0.0853(7) Uani d D 1 O
C1 0.1796(3) 0.44715(15) 0.7545(3) 0.0562(6) Uani d . 1 C
C2 0.2928(3) 0.50325(17) 0.9156(2) 0.0605(6) Uani d . 1 C
C3 0.3218(3) 0.42300(18) 0.9233(3) 0.0660(7) Uani d . 1 C
C4 0.0061(3) 0.74458(16) 0.5558(2) 0.0562(6) Uani d . 1 C
C5 0.1319(3) 0.80922(15) 0.7008(2) 0.0552(6) Uani d . 1 C
C6 0.0843(3) 0.86452(15) 0.6139(3) 0.0582(6) Uani d . 1 C
C7 0.4088(2) 0.68862(13) 0.8054(2) 0.0472(5) Uani d . 1 C
C8 0.4278(2) 0.67252(15) 0.6708(2) 0.0510(5) Uani d . 1 C
C9 0.3300(2) 0.58693(13) 0.49955(19) 0.0417(4) Uani d . 1 C
C10 0.4383(2) 0.59762(15) 0.4350(2) 0.0500(5) Uani d . 1 C
C11 0.4397(2) 0.55467(16) 0.3251(2) 0.0559(6) Uani d . 1 C
C12 0.3365(2) 0.50259(16) 0.2802(2) 0.0498(5) Uani d . 1 C
C13 0.2271(2) 0.49280(12) 0.34492(19) 0.0392(4) Uani d . 1 C
C14 0.2242(2) 0.53554(13) 0.45458(19) 0.0398(4) Uani d . 1 C
C15 0.1119(2) 0.43824(13) 0.2944(2) 0.0419(5) Uani d . 1 C
H1W1 0.217(3) 0.1972(11) 0.703(4) 0.128 Uiso d D 1 H
H1W2 0.326(2) 0.240(2) 0.671(4) 0.128 Uiso d D 1 H
H1 0.1223 0.4391 0.6802 0.067 Uiso calc R 1 H
H2 0.3280 0.5424 0.9731 0.073 Uiso calc R 1 H
H3 0.3790 0.3967 0.9859 0.079 Uiso calc R 1 H
H4 -0.0409 0.7038 0.5083 0.067 Uiso calc R 1 H
H5 0.1892 0.8205 0.7740 0.066 Uiso calc R 1 H
H6 0.1020 0.9201 0.6158 0.070 Uiso calc R 1 H
H8A 0.4319 0.7238 0.6272 0.061 Uiso calc R 1 H
H8B 0.5122 0.6438 0.6685 0.061 Uiso calc R 1 H
H10 0.5085 0.6328 0.4645 0.060 Uiso calc R 1 H
H11 0.5121 0.5613 0.2809 0.067 Uiso calc R 1 H
H12 0.3398 0.4740 0.2068 0.060 Uiso calc R 1 H
H14 0.1511 0.5297 0.4981 0.048 Uiso calc R 1 H
H16 0.2489 0.3376 0.8001 0.075 Uiso calc R 1 H
H17 -0.0369 0.8438 0.4564 0.070 Uiso calc R 1 H
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
_geom_angle_publ_flag
N1 Cu1 O3 . . 90.76(7) yes
N3 Cu1 N1 . . 179.65(8) yes
N3 Cu1 O3 . . 89.02(7) yes
O1 Cu1 N1 . . 89.07(8) yes
O1 Cu1 N3 . . 90.62(8) yes
O1 Cu1 O3 . . 75.39(6) yes
O1 Cu1 O4 . 3_566 176.45(7) yes
O4 Cu1 N1 3_566 . 88.60(8) yes
O4 Cu1 N3 3_566 . 91.72(7) yes
O4 Cu1 O3 3_566 . 107.31(6) yes
O5 Cu1 N1 3_566 . 88.52(7) yes
O5 Cu1 N3 3_566 . 91.83(7) yes
O5 Cu1 O1 3_566 . 125.82(7) yes
O5 Cu1 O3 3_566 . 158.76(6) yes
O5 Cu1 O4 3_566 3_566 51.45(6) yes
N1 C1 N2 . . 110.8(2) no
N1 C1 H1 . . 124.6 no
N1 C2 H2 . . 125.2 no
N2 C1 H1 . . 124.6 no
N2 C3 H3 . . 127.1 no
N3 C4 N4 . . 110.8(2) no
N3 C4 H4 . . 124.6 no
N3 C5 H5 . . 125.3 no
N4 C4 H4 . . 124.6 no
N4 C6 H6 . . 126.9 no
O1 C7 C8 . . 119.82(19) no
O2 C7 O1 . . 123.7(2) no
O2 C7 C8 . . 116.5(2) no
O3 C8 C7 . . 109.98(19) no
O3 C8 H8A . . 109.7 no
O3 C8 H8B . . 109.7 no
O3 C9 C10 . . 123.8(2) no
O3 C9 C14 . . 115.40(18) no
O4 C15 C13 . . 117.57(18) no
O5 C15 O4 . . 123.6(2) no
O5 C15 C13 . . 118.85(19) no
C1 N1 C2 . . 105.8(2) no
C1 N1 Cu1 . . 125.38(17) no
C1 N2 C3 . . 108.0(2) no
C1 N2 H16 . . 126.0 no
C2 N1 Cu1 . . 128.13(18) no
C2 C3 N2 . . 105.7(3) no
C2 C3 H3 . . 127.1 no
C3 N2 H16 . . 126.0 no
C3 C2 N1 . . 109.6(3) no
C3 C2 H2 . . 125.2 no
C4 N3 Cu1 . . 125.85(17) no
C4 N3 C5 . . 105.1(2) no
C4 N4 C6 . . 108.5(2) no
C4 N4 H17 . . 125.8 no
C5 N3 Cu1 . . 127.80(16) no
C5 C6 N4 . . 106.3(2) no
C5 C6 H6 . . 126.9 no
C6 N4 H17 . . 125.8 no
C6 C5 N3 . . 109.4(2) no
C6 C5 H5 . . 125.3 no
C7 O1 Cu1 . . 124.16(15) no
C7 C8 H8A . . 109.7 no
C7 C8 H8B . . 109.7 no
C8 O3 Cu1 . . 108.58(13) no
C9 O3 Cu1 . . 131.81(13) no
C9 O3 C8 . . 119.59(17) no
C9 C10 C11 . . 118.5(2) no
C9 C10 H10 . . 120.8 no
C9 C14 H14 . . 119.9 no
C10 C9 C14 . . 120.8(2) no
C10 C11 H11 . . 119.3 no
C11 C10 H10 . . 120.8 no
C11 C12 C13 . . 119.8(2) no
C11 C12 H12 . . 120.1 no
C12 C11 C10 . . 121.4(2) no
C12 C11 H11 . . 119.3 no
C12 C13 C15 . . 120.13(19) no
C13 C12 H12 . . 120.1 no
C13 C14 C9 . . 120.18(19) no
C13 C14 H14 . . 119.9 no
C14 C13 C12 . . 119.3(2) no
C14 C13 C15 . . 120.53(18) no
C15 O4 Cu1 . 3_566 111.66(13) no
H1W1 O1W H1W2 . . 108.0(16) no
H8A C8 H8B . . 108.2 no
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 . 1.994(2) yes
Cu1 N3 . 1.9837(19) yes
Cu1 O1 . 1.9513(16) yes
Cu1 O3 . 2.3814(18) yes
Cu1 O4 3_566 1.9810(15) yes
Cu1 O5 3_566 2.8191(15) yes
O1 C7 . 1.266(3) yes
O2 C7 . 1.238(3) yes
O4 C15 . 1.273(3) yes
O5 C15 . 1.243(3) yes
N1 C1 . 1.318(3) no
N1 C2 . 1.377(3) no
N2 C1 . 1.334(3) no
N2 C3 . 1.372(4) no
N2 H16 . 0.8600 no
N3 C4 . 1.321(3) no
N3 C5 . 1.388(3) no
N4 C4 . 1.337(3) no
N4 C6 . 1.349(3) no
N4 H17 . 0.8600 no
O3 C8 . 1.424(3) no
O3 C9 . 1.379(3) no
O4 Cu1 3_566 1.9810(15) no
O1W H1W1 . 0.856(10) no
O1W H1W2 . 0.858(10) no
C1 H1 . 0.9300 no
C2 C3 . 1.350(4) no
C2 H2 . 0.9300 no
C3 H3 . 0.9300 no
C4 H4 . 0.9300 no
C5 C6 . 1.347(4) no
C5 H5 . 0.9300 no
C6 H6 . 0.9300 no
C7 C8 . 1.523(3) no
C8 H8A . 0.9700 no
C8 H8B . 0.9700 no
C9 C10 . 1.382(3) no
C9 C14 . 1.386(3) no
C10 C11 . 1.388(3) no
C10 H10 . 0.9300 no
C11 C12 . 1.375(3) no
C11 H11 . 0.9300 no
C12 C13 . 1.391(3) no
C12 H12 . 0.9300 no
C13 C14 . 1.386(3) no
C13 C15 . 1.500(3) no
C14 H14 . 0.9300 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
_geom_hbond_publ_flag
N2 H16 O1W . 0.86 1.90 2.712(3) 158 yes
N4 H17 O5 2 0.86 1.96 2.812(3) 171 yes
O1W H1W1 O5 4_566 0.85(2) 1.96(3) 2.802(3) 168(4) yes
O1W H1W2 O2 2_646 0.85(2) 1.84(3) 2.691(3) 172(4) yes
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
_geom_torsion_publ_flag
Cu1 N1 C1 N2 . 171.33(16) no
Cu1 N1 C2 C3 . -171.30(18) no
Cu1 N3 C4 N4 . -167.86(17) no
Cu1 N3 C5 C6 . 167.67(19) no
Cu1 O1 C7 O2 . -172.42(17) no
Cu1 O1 C7 C8 . 8.4(3) no
Cu1 O3 C8 C7 . 14.1(2) no
Cu1 O3 C9 C10 . 175.81(17) no
Cu1 O3 C9 C14 . -4.3(3) no
Cu1 O4 C15 O5 3_566 -10.1(3) no
Cu1 O4 C15 C13 3_566 168.75(14) no
N1 Cu1 O1 C7 . 91.36(18) no
N1 Cu1 O3 C8 . -97.64(16) no
N1 Cu1 O3 C9 . 80.6(2) no
N1 C2 C3 N2 . 0.4(3) no
N3 Cu1 O1 C7 . -88.49(18) no
N3 Cu1 O3 C8 . 82.10(16) no
N3 Cu1 O3 C9 . -99.7(2) no
N3 C5 C6 N4 . -0.3(3) no
O1 Cu1 N1 C1 . -153.1(2) no
O1 Cu1 N1 C2 . 16.3(2) no
O1 Cu1 N3 C4 . 156.7(2) no
O1 Cu1 N3 C5 . -8.3(2) no
O1 Cu1 O3 C8 . -8.80(15) no
O1 Cu1 O3 C9 . 169.4(2) no
O1 C7 C8 O3 . -15.8(3) no
O2 C7 C8 O3 . 164.9(2) no
O3 Cu1 N1 C1 . -77.7(2) no
O3 Cu1 N1 C2 . 91.7(2) no
O3 Cu1 N3 C4 . 81.3(2) no
O3 Cu1 N3 C5 . -83.7(2) no
O3 Cu1 O1 C7 . 0.33(17) no
O3 C9 C10 C11 . 178.8(2) no
O3 C9 C14 C13 . -178.59(19) no
O4 Cu1 N1 C1 3_566 29.6(2) no
O4 Cu1 N1 C2 3_566 -161.0(2) no
O4 Cu1 N3 C4 3_566 -26.0(2) no
O4 Cu1 N3 C5 3_566 169.0(2) no
O4 Cu1 O3 C8 3_566 173.59(15) no
O4 Cu1 O3 C9 3_566 -8.2(2) no
C1 N1 C2 C3 . -0.3(3) no
C1 N2 C3 C2 . -0.4(3) no
C2 N1 C1 N2 . 0.0(3) no
C3 N2 C1 N1 . 0.3(3) no
C4 N3 C5 C6 . 0.2(3) no
C4 N4 C6 C5 . 0.2(3) no
C5 N3 C4 N4 . -0.1(3) no
C6 N4 C4 N3 . -0.1(3) no
C8 O3 C9 C10 . -6.1(3) no
C8 O3 C9 C14 . 173.7(2) no
C9 O3 C8 C7 . -164.43(19) no
C9 C10 C11 C12 . 0.1(4) no
C10 C9 C14 C13 . 1.3(3) no
C10 C11 C12 C13 . 0.6(4) no
C11 C12 C13 C14 . -0.4(3) no
C11 C12 C13 C15 . 178.0(2) no
C12 C13 C14 C9 . -0.5(3) no
C12 C13 C15 O4 . 178.5(2) no
C12 C13 C15 O5 . -2.7(3) no
C14 C9 C10 C11 . -1.0(4) no
C14 C13 C15 O4 . -3.2(3) no
C14 C13 C15 O5 . 175.7(2) no
C15 C13 C14 C9 . -178.87(19) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139067243
