#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/82/2208282.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_2208282
loop_
_publ_author_name
'Dong, Gui-Ying'
'Cui, Guang-Hua'
'Wang, Sheng-chun'
_publ_section_title
;μ-1,1'-Methylenedi-1H-imidazole-κ²N³:N^3'^-bis[aqua(pyridine-2,6-dicarboxylato)copper(II)]
 tetrahydrate
;
_journal_coeditor_code           CI2004
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m606
_journal_page_last               m607
_journal_paper_doi               10.1107/S1600536806006350
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Cu2 (C7 H3 N O4)2 (C7 H8 N4) (H2 O)2], 4H2 O'
_chemical_formula_moiety         'C21 H18 Cu2 N6 O10, 4H2 O'
_chemical_formula_sum            'C21 H26 Cu2 N6 O14'
_chemical_formula_weight         713.56
_chemical_name_systematic
;
μ-1,1'-Methylenedi-1H-imidazole-κ²N³:N^3'^-bis[aqua(pyridine-2,6-
dicarboxylato)copper(II)] tetrahydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 99.15(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   35.376(7)
_cell_length_b                   5.1136(10)
_cell_length_c                   14.868(3)
_cell_measurement_reflns_used    920
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      4.5
_cell_volume                     2655.4(9)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11796
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.18
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.686
_exptl_absorpt_correction_T_max  0.7742
_exptl_absorpt_correction_T_min  0.7292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2962
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0357P)²+4.4628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                2526
_reflns_number_total             2962
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2004.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2208282
_cod_database_fobs_code          2208282
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Cu Cu1 0.383916(7) 1.00943(5) 0.380558(19) 0.02604(10) Uani d . 1
O O1 0.41248(5) 0.3838(4) 0.53867(15) 0.0478(5) Uani d . 1
O O2 0.41679(5) 0.7214(3) 0.44544(12) 0.0337(4) Uani d . 1
O O3 0.34148(4) 1.2863(3) 0.35591(11) 0.0306(4) Uani d . 1
O O4 0.28438(5) 1.3883(4) 0.39378(13) 0.0393(4) Uani d . 1
N N1 0.35272(5) 0.9107(4) 0.46898(12) 0.0243(4) Uani d . 1
N N2 0.41898(5) 1.1311(4) 0.30081(13) 0.0281(4) Uani d . 1
N N3 0.46658(5) 1.3255(4) 0.25057(13) 0.0282(4) Uani d . 1
C C1 0.32040(6) 1.0405(4) 0.47200(16) 0.0269(5) Uani d . 1
C C2 0.31397(6) 1.2561(5) 0.40212(16) 0.0279(5) Uani d . 1
C C3 0.29737(7) 0.9724(5) 0.53546(19) 0.0381(6) Uani d . 1
H H3 0.2747 1.0614 0.5384 0.046 Uiso calc R 1
C C4 0.30913(8) 0.7689(6) 0.59410(18) 0.0429(6) Uani d . 1
H H4 0.2944 0.7219 0.6380 0.051 Uiso calc R 1
C C5 0.34265(7) 0.6333(5) 0.58853(17) 0.0367(6) Uani d . 1
H H5 0.3504 0.4942 0.6274 0.044 Uiso calc R 1
C C6 0.36411(6) 0.7112(4) 0.52353(15) 0.0269(5) Uani d . 1
C C7 0.40100(7) 0.5910(5) 0.50269(16) 0.0301(5) Uani d . 1
C C8 0.42379(7) 1.0184(5) 0.21932(18) 0.0356(5) Uani d . 1
H H8 0.4091 0.8826 0.1905 0.043 Uiso calc R 1
C C9 0.45317(7) 1.1361(5) 0.18794(17) 0.0359(6) Uani d . 1
H H9 0.4625 1.0970 0.1345 0.043 Uiso calc R 1
C C10 0.5000 1.4890(6) 0.2500 0.0341(8) Uani d S 1
H H10A 0.5037 1.6002 0.3035 0.041 Uiso d R 1
C C11 0.44511(6) 1.3151(5) 0.31729(16) 0.0299(5) Uani d . 1
H H11 0.4483 1.4233 0.3682 0.036 Uiso calc R 1
O O1W 0.35165(5) 0.7496(4) 0.26921(12) 0.0349(4) Uani d D 1
H H1WA 0.3506(8) 0.600(3) 0.293(2) 0.062(11) Uiso d D 1
H H1WB 0.3293(4) 0.807(6) 0.258(2) 0.059(11) Uiso d D 1
O O2W 0.48923(7) 0.2507(7) 0.53592(18) 0.0894(10) Uani d . 1
H H2WA 0.4695 0.3302 0.5243 0.134 Uiso d R 1
H H2WB 0.5042 0.2895 0.5022 0.134 Uiso d R 1
O O3W 0.27331(6) 0.8163(4) 0.27300(18) 0.0552(6) Uani d D 1
H H3WA 0.2748(10) 0.684(5) 0.306(2) 0.077(13) Uiso d D 1
H H3WB 0.2576(9) 0.794(7) 0.2256(15) 0.083(14) Uiso d D 1
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'
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
_geom_angle_publ_flag
N1 Cu1 N2 . 173.90(8) yes
N1 Cu1 O2 . 80.27(7) yes
N2 Cu1 O2 . 98.58(7) yes
N1 Cu1 O3 . 79.60(7) yes
N2 Cu1 O3 . 100.91(7) yes
O2 Cu1 O3 . 159.25(7) yes
N1 Cu1 O1W . 93.92(7) yes
N2 Cu1 O1W . 92.16(7) yes
O2 Cu1 O1W . 96.04(7) yes
O3 Cu1 O1W . 90.28(7) yes
C7 O2 Cu1 . 114.72(14) ?
C2 O3 Cu1 . 114.55(14) ?
C6 N1 C1 . 122.9(2) ?
C6 N1 Cu1 . 118.11(15) ?
C1 N1 Cu1 . 119.00(16) ?
C11 N2 C8 . 106.39(19) ?
C11 N2 Cu1 . 127.72(16) ?
C8 N2 Cu1 . 125.55(17) ?
C11 N3 C9 . 107.33(19) ?
C11 N3 C10 . 125.79(19) ?
C9 N3 C10 . 126.62(17) ?
N1 C1 C3 . 120.0(2) ?
N1 C1 C2 . 112.23(19) ?
C3 C1 C2 . 127.8(2) ?
O4 C2 O3 . 125.6(2) ?
O4 C2 C1 . 120.1(2) ?
O3 C2 C1 . 114.31(19) ?
C4 C3 C1 . 118.0(2) ?
C4 C3 H3 . 121.0 ?
C1 C3 H3 . 121.0 ?
C3 C4 C5 . 121.0(2) ?
C3 C4 H4 . 119.5 ?
C5 C4 H4 . 119.5 ?
C6 C5 C4 . 117.9(2) ?
C6 C5 H5 . 121.0 ?
C4 C5 H5 . 121.0 ?
N1 C6 C5 . 120.2(2) ?
N1 C6 C7 . 111.96(19) ?
C5 C6 C7 . 127.8(2) ?
O1 C7 O2 . 126.3(2) ?
O1 C7 C6 . 119.8(2) ?
O2 C7 C6 . 114.0(2) ?
C9 C8 N2 . 109.1(2) ?
C9 C8 H8 . 125.4 ?
N2 C8 H8 . 125.4 ?
C8 C9 N3 . 106.4(2) ?
C8 C9 H9 . 126.8 ?
N3 C9 H9 . 126.8 ?
N3 C10 N3 2_655 109.5(3) ?
N3 C10 H10A 2_655 109.8 ?
N3 C10 H10A . 109.8 ?
N2 C11 N3 . 110.7(2) ?
N2 C11 H11 . 124.6 ?
N3 C11 H11 . 124.6 ?
Cu1 O1W H1WA . 106(2) ?
Cu1 O1W H1WB . 107(2) ?
H1WA O1W H1WB . 107(2) ?
H2WA O2W H2WB . 112.1 ?
H3WA O3W H3WB . 111(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 N1 . 1.9137(18) yes
Cu1 N2 . 1.9492(18) yes
Cu1 O2 . 2.0240(17) yes
Cu1 O3 . 2.0537(16) yes
Cu1 O1W . 2.2820(19) yes
O1 C7 . 1.227(3) ?
O2 C7 . 1.277(3) ?
O3 C2 . 1.287(3) ?
O4 C2 . 1.236(3) ?
N1 C6 . 1.325(3) ?
N1 C1 . 1.329(3) ?
N2 C11 . 1.314(3) ?
N2 C8 . 1.377(3) ?
N3 C11 . 1.343(3) ?
N3 C9 . 1.375(3) ?
N3 C10 . 1.449(3) ?
C1 C3 . 1.386(3) ?
C1 C2 . 1.507(3) ?
C3 C4 . 1.379(4) ?
C3 H3 . 0.93 ?
C4 C5 . 1.388(4) ?
C4 H4 . 0.93 ?
C5 C6 . 1.379(3) ?
C5 H5 . 0.93 ?
C6 C7 . 1.519(3) ?
C8 C9 . 1.347(3) ?
C8 H8 . 0.93 ?
C9 H9 . 0.93 ?
C10 N3 2_655 1.449(3) ?
C10 H10A . 0.97 ?
C11 H11 . 0.93 ?
O1W H1WA . 0.840(10) ?
O1W H1WB . 0.840(10) ?
O2W H2WA . 0.80 ?
O2W H2WB . 0.81 ?
O3W H3WA . 0.830(10) ?
O3W H3WB . 0.830(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
O1W H1WA O3 1_545 0.840(10) 1.91(2) 2.748(3) 170(3)
O1W H1WB O3W 1_555 0.840(10) 2.03(3) 2.802(3) 154(3)
O2W H2WA O1 1_555 0.80 2.08 2.806(3) 150
O2W H2WB O2W 5_666 0.81 2.44 2.912(5) 118
O3W H3WA O4 1_545 0.830(10) 1.99(3) 2.819(3) 173(3)
O3W H3WB O4 4_545 0.830(10) 2.18(3) 2.973(3) 159(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_4
_geom_torsion
N1 Cu1 O2 C7 . 8.39(17)
N2 Cu1 O2 C7 . -177.68(17)
O3 Cu1 O2 C7 . 22.5(3)
O1W Cu1 O2 C7 . -84.56(17)
N1 Cu1 O3 C2 . -5.05(16)
N2 Cu1 O3 C2 . -178.86(16)
O2 Cu1 O3 C2 . -19.2(3)
O1W Cu1 O3 C2 . 88.88(16)
O2 Cu1 N1 C6 . -3.39(17)
O3 Cu1 N1 C6 . -178.36(18)
O1W Cu1 N1 C6 . 92.08(17)
O2 Cu1 N1 C1 . 177.92(19)
O3 Cu1 N1 C1 . 2.95(17)
O1W Cu1 N1 C1 . -86.61(18)
O2 Cu1 N2 C11 . -90.5(2)
O3 Cu1 N2 C11 . 82.3(2)
O1W Cu1 N2 C11 . 173.0(2)
O2 Cu1 N2 C8 . 81.8(2)
O3 Cu1 N2 C8 . -105.3(2)
O1W Cu1 N2 C8 . -14.6(2)
C6 N1 C1 C3 . 1.4(4)
Cu1 N1 C1 C3 . -179.98(19)
C6 N1 C1 C2 . -179.3(2)
Cu1 N1 C1 C2 . -0.7(3)
Cu1 O3 C2 O4 . -174.8(2)
Cu1 O3 C2 C1 . 6.0(2)
N1 C1 C2 O4 . 177.1(2)
C3 C1 C2 O4 . -3.7(4)
N1 C1 C2 O3 . -3.7(3)
C3 C1 C2 O3 . 175.5(2)
N1 C1 C3 C4 . 0.0(4)
C2 C1 C3 C4 . -179.1(2)
C1 C3 C4 C5 . -1.2(4)
C3 C4 C5 C6 . 1.0(4)
C1 N1 C6 C5 . -1.6(4)
Cu1 N1 C6 C5 . 179.79(19)
C1 N1 C6 C7 . 177.4(2)
Cu1 N1 C6 C7 . -1.3(3)
C4 C5 C6 N1 . 0.3(4)
C4 C5 C6 C7 . -178.4(2)
Cu1 O2 C7 O1 . 167.3(2)
Cu1 O2 C7 C6 . -11.1(3)
N1 C6 C7 O1 . -170.2(2)
C5 C6 C7 O1 . 8.7(4)
N1 C6 C7 O2 . 8.4(3)
C5 C6 C7 O2 . -172.8(2)
C11 N2 C8 C9 . 0.4(3)
Cu1 N2 C8 C9 . -173.31(18)
N2 C8 C9 N3 . -0.4(3)
C11 N3 C9 C8 . 0.2(3)
C10 N3 C9 C8 . 174.6(2)
C11 N3 C10 N3 2_655 116.7(2)
C9 N3 C10 N3 2_655 -56.6(2)
C8 N2 C11 N3 . -0.2(3)
Cu1 N2 C11 N3 . 173.29(16)
C9 N3 C11 N2 . 0.0(3)
C10 N3 C11 N2 . -174.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139069129
