#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/58/2215803.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_2215803
loop_
_publ_author_name
'Shouwen Jin'
'Daqi Wang'
_publ_section_title
;
 Bis[μ-bis(imidazol-1-yl)methane]bis[aqua(oxalato)copper(II)]
 dihydrate
;
_journal_coeditor_code           BT2533
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2755
_journal_page_last               m2756
_journal_paper_doi               10.1107/S1600536807050465
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu2 (C2 O4)2 (C7 H8 N4)2 (H2 O)2] , 2H2 O'
_chemical_formula_moiety         'C18 H20 Cu2 N8 O10 , 2H2 O'
_chemical_formula_sum            'C18 H24 Cu2 N8 O12'
_chemical_formula_weight         671.53
_chemical_name_systematic
;
bis[μ-bis(imidazol-1-yl)methane]bis[aqua(oxalato)copper(II)] dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                117.964(4)
_cell_angle_beta                 104.582(5)
_cell_angle_gamma                91.773(5)
_cell_formula_units_Z            1
_cell_length_a                   7.970(4)
_cell_length_b                   9.770(4)
_cell_length_c                   9.913(4)
_cell_measurement_reflns_used    2374
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.037
_cell_measurement_theta_min      2.397
_cell_volume                     649.7(5)
_computing_cell_refinement       'SMART (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1996)'
_computing_publication_material  'SHELXTL (Siemens, 1996)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Siemens 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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3367
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    1.713
_exptl_absorpt_correction_T_max  0.4874
_exptl_absorpt_correction_T_min  0.4526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             342
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.49
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.361
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2248
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0273
_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)+(0.0326P)²+0.2553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0717
_reflns_number_gt                1997
_reflns_number_total             2248
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2533.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2215803
_cod_database_fobs_code          2215803
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.86641(4) 0.71911(3) 0.95989(3) 0.02912(12) Uani d . 1
N N1 0.7745(3) 0.3018(2) 0.5408(2) 0.0287(5) Uani d . 1
N N2 0.8596(3) 0.5362(2) 0.7528(2) 0.0285(5) Uani d . 1
N N3 0.5694(3) 0.1755(2) 0.2769(2) 0.0276(5) Uani d . 1
N N4 0.3642(3) 0.2364(2) 0.1309(2) 0.0296(5) Uani d . 1
O O1 1.1180(2) 0.7196(2) 1.0468(2) 0.0360(4) Uani d . 1
O O2 1.3453(2) 0.8662(2) 1.2644(2) 0.0414(5) Uani d . 1
O O3 0.9116(2) 0.9180(2) 1.1597(2) 0.0450(5) Uani d . 1
O O4 1.1263(3) 1.0719(3) 1.3829(3) 0.0731(8) Uani d . 1
O O5 0.7390(3) 0.5676(2) 1.0311(2) 0.0476(5) Uani d . 1
H H11 0.7729 0.4808 1.0134 0.071 Uiso d R 1
H H12 0.7205 0.6120 1.1217 0.071 Uiso d R 1
O O6 0.6384(3) 0.7255(3) 0.3125(3) 0.0540(6) Uani d . 1
H H13 0.5560 0.7690 0.2849 0.081 Uiso d R 1
H H14 0.7054 0.8012 0.3997 0.081 Uiso d R 1
C C1 0.6634(4) 0.1548(3) 0.4106(3) 0.0338(6) Uani d . 1
H H1A 0.7356 0.0746 0.3750 0.041 Uiso calc R 1
H H1B 0.5795 0.1197 0.4486 0.041 Uiso calc R 1
C C2 0.7277(3) 0.4185(3) 0.6587(3) 0.0305(6) Uani d . 1
H H2 0.6164 0.4162 0.6720 0.037 Uiso calc R 1
C C3 0.9981(3) 0.4921(3) 0.6917(3) 0.0363(6) Uani d . 1
H H3 1.1099 0.5524 0.7345 0.044 Uiso calc R 1
C C4 0.9473(3) 0.3485(3) 0.5607(3) 0.0388(7) Uani d . 1
H H4 1.0155 0.2923 0.4966 0.047 Uiso calc R 1
C C5 0.4070(3) 0.2121(3) 0.2547(3) 0.0304(6) Uani d . 1
H H5A 0.3350 0.2192 0.3176 0.036 Uiso calc R 1
C C6 0.5059(3) 0.2145(3) 0.0727(3) 0.0337(6) Uani d . 1
H H6 0.5134 0.2241 -0.0147 0.040 Uiso calc R 1
C C7 0.6329(3) 0.1769(3) 0.1621(3) 0.0329(6) Uani d . 1
H H7 0.7422 0.1561 0.1481 0.040 Uiso calc R 1
C C8 1.1908(3) 0.8376(3) 1.1850(3) 0.0282(5) Uani d . 1
C C9 1.0674(3) 0.9537(3) 1.2509(3) 0.0376(6) Uani 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'
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
O3 Cu1 O1 . . 83.29(7)
O3 Cu1 N2 . . 169.00(9)
O1 Cu1 N2 . . 90.02(8)
O3 Cu1 N4 . 2_666 91.17(8)
O1 Cu1 N4 . 2_666 165.88(8)
N2 Cu1 N4 . 2_666 93.33(8)
O3 Cu1 O5 . . 97.83(9)
O1 Cu1 O5 . . 101.59(8)
N2 Cu1 O5 . . 92.04(9)
N4 Cu1 O5 2_666 . 92.01(9)
C2 N1 C4 . . 107.3(2)
C2 N1 C1 . . 127.3(2)
C4 N1 C1 . . 125.3(2)
C2 N2 C3 . . 105.8(2)
C2 N2 Cu1 . . 125.91(17)
C3 N2 Cu1 . . 127.46(17)
C5 N3 C7 . . 107.7(2)
C5 N3 C1 . . 124.9(2)
C7 N3 C1 . . 127.2(2)
C5 N4 C6 . . 106.1(2)
C5 N4 Cu1 . 2_666 126.32(17)
C6 N4 Cu1 . 2_666 127.45(18)
C8 O1 Cu1 . . 113.30(15)
C9 O3 Cu1 . . 113.63(16)
Cu1 O5 H11 . . 118.7
Cu1 O5 H12 . . 117.8
H11 O5 H12 . . 110.1
H13 O6 H14 . . 103.0
N3 C1 N1 . . 110.6(2)
N3 C1 H1A . . 109.5
N1 C1 H1A . . 109.5
N3 C1 H1B . . 109.5
N1 C1 H1B . . 109.5
H1A C1 H1B . . 108.1
N2 C2 N1 . . 111.1(2)
N2 C2 H2 . . 124.4
N1 C2 H2 . . 124.4
C4 C3 N2 . . 109.8(2)
C4 C3 H3 . . 125.1
N2 C3 H3 . . 125.1
C3 C4 N1 . . 106.0(2)
C3 C4 H4 . . 127.0
N1 C4 H4 . . 127.0
N4 C5 N3 . . 110.4(2)
N4 C5 H5A . . 124.8
N3 C5 H5A . . 124.8
C7 C6 N4 . . 109.4(2)
C7 C6 H6 . . 125.3
N4 C6 H6 . . 125.3
C6 C7 N3 . . 106.4(2)
C6 C7 H7 . . 126.8
N3 C7 H7 . . 126.8
O2 C8 O1 . . 126.3(2)
O2 C8 C9 . . 119.4(2)
O1 C8 C9 . . 114.3(2)
O4 C9 O3 . . 125.5(3)
O4 C9 C8 . . 119.0(2)
O3 C9 C8 . . 115.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 O3 . 1.9537(19)
Cu1 O1 . 1.9717(19)
Cu1 N2 . 1.977(2)
Cu1 N4 2_666 1.991(2)
Cu1 O5 . 2.229(2)
N1 C2 . 1.342(3)
N1 C4 . 1.373(3)
N1 C1 . 1.456(3)
N2 C2 . 1.313(3)
N2 C3 . 1.376(3)
N3 C5 . 1.345(3)
N3 C7 . 1.362(3)
N3 C1 . 1.456(3)
N4 C5 . 1.322(3)
N4 C6 . 1.372(3)
N4 Cu1 2_666 1.991(2)
O1 C8 . 1.273(3)
O2 C8 . 1.224(3)
O3 C9 . 1.262(3)
O4 C9 . 1.227(3)
O5 H11 . 0.8499
O5 H12 . 0.8499
O6 H13 . 0.8500
O6 H14 . 0.8500
C1 H1A . 0.9700
C1 H1B . 0.9700
C2 H2 . 0.9300
C3 C4 . 1.345(4)
C3 H3 . 0.9300
C4 H4 . 0.9300
C5 H5A . 0.9300
C6 C7 . 1.350(4)
C6 H6 . 0.9300
C7 H7 . 0.9300
C8 C9 . 1.542(4)
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
O6 H14 O4 2_777 0.85 1.98 2.804(3) 163.5
O6 H13 O2 1_454 0.85 1.97 2.797(3) 165.1
O5 H12 O6 1_556 0.85 1.98 2.823(3) 169.3
O5 H11 O1 2_767 0.85 2.05 2.895(3) 170.4
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
O3 Cu1 N2 C2 . -164.4(4)
O1 Cu1 N2 C2 . 143.2(2)
N4 Cu1 N2 C2 2_666 -50.5(2)
O5 Cu1 N2 C2 . 41.6(2)
O3 Cu1 N2 C3 . 27.7(5)
O1 Cu1 N2 C3 . -24.6(2)
N4 Cu1 N2 C3 2_666 141.7(2)
O5 Cu1 N2 C3 . -126.2(2)
O3 Cu1 O1 C8 . 1.64(18)
N2 Cu1 O1 C8 . 172.90(18)
N4 Cu1 O1 C8 2_666 69.1(4)
O5 Cu1 O1 C8 . -95.02(19)
O1 Cu1 O3 C9 . -2.0(2)
N2 Cu1 O3 C9 . -54.8(5)
N4 Cu1 O3 C9 2_666 -169.0(2)
O5 Cu1 O3 C9 . 98.9(2)
C5 N3 C1 N1 . -92.8(3)
C7 N3 C1 N1 . 80.5(3)
C2 N1 C1 N3 . 86.0(3)
C4 N1 C1 N3 . -91.2(3)
C3 N2 C2 N1 . -0.1(3)
Cu1 N2 C2 N1 . -170.06(16)
C4 N1 C2 N2 . -0.3(3)
C1 N1 C2 N2 . -177.8(2)
C2 N2 C3 C4 . 0.4(3)
Cu1 N2 C3 C4 . 170.18(19)
N2 C3 C4 N1 . -0.6(3)
C2 N1 C4 C3 . 0.5(3)
C1 N1 C4 C3 . 178.1(2)
C6 N4 C5 N3 . -0.1(3)
Cu1 N4 C5 N3 2_666 176.06(15)
C7 N3 C5 N4 . 0.1(3)
C1 N3 C5 N4 . 174.5(2)
C5 N4 C6 C7 . 0.1(3)
Cu1 N4 C6 C7 2_666 -176.04(17)
N4 C6 C7 N3 . 0.0(3)
C5 N3 C7 C6 . 0.0(3)
C1 N3 C7 C6 . -174.2(2)
Cu1 O1 C8 O2 . -179.4(2)
Cu1 O1 C8 C9 . -1.1(3)
Cu1 O3 C9 O4 . -179.4(3)
Cu1 O3 C9 C8 . 1.9(3)
O2 C8 C9 O4 . -0.9(4)
O1 C8 C9 O4 . -179.3(3)
O2 C8 C9 O3 . 177.9(2)
O1 C8 C9 O3 . -0.6(4)
