#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/58/2215842.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_2215842
loop_
_publ_author_name
'Liang Wang'
'Xiu-Ying Li'
'Yang Liu'
'Jian Wang'
_publ_section_title
;catena-Poly[[[bis(2-methyl-1H-imidazole-κN³)copper(II)]-μ-biphenyl-2,2'-dicarboxylato-κ²O:O']
 dihydrate]
;
_journal_coeditor_code           CI2473
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2636
_journal_page_last               m2636
_journal_paper_doi               10.1107/S160053680704723X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu (C14 H8 O4) (C4 H6 N2)2], 2H2 O'
_chemical_formula_moiety         'C22 H20 Cu N4 O4, 2H2 O'
_chemical_formula_sum            'C22 H24 Cu N4 O6'
_chemical_formula_weight         503.99
_chemical_name_systematic
;
catena-Poly[[[bis(2-methyl-1H-imidazole-\kN³)copper(II)]-
μ-biphenyl-2,2'-dicarboxylato-κ²O:O'] dihydrate]
;
_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_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                 104.65(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7554(18)
_cell_length_b                   17.940(4)
_cell_length_c                   16.116(3)
_cell_measurement_reflns_used    17307
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.01
_cell_volume                     2449.1(9)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1990)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23229
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.935
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.316
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5578
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0432
_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)+(0.0409P)²+1.0153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                4004
_reflns_number_total             5578
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2473.cif
_cod_data_source_block           I
_cod_original_cell_volume        2449.0(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2215842
_cod_database_fobs_code          2215842
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_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
C C1 -0.0628(3) 0.14907(16) 0.89714(17) 0.0417(6) Uani d . 1
C C2 0.0462(4) 0.09492(19) 0.9508(2) 0.0650(9) Uani d . 1
H H2A -0.0049 0.0716 0.9902 0.097 Uiso calc R 1
H H2B 0.1394 0.1203 0.9822 0.097 Uiso calc R 1
H H2C 0.0748 0.0576 0.9147 0.097 Uiso calc R 1
C C3 -0.2843(4) 0.2071(2) 0.8369(2) 0.0628(9) Uani d . 1
H H3 -0.3902 0.2207 0.8210 0.075 Uiso calc R 1
C C4 -0.1646(3) 0.23935(19) 0.81210(19) 0.0527(8) Uani d . 1
H H4 -0.1740 0.2799 0.7752 0.063 Uiso calc R 1
C C5 0.1416(4) 0.29497(18) 1.00860(19) 0.0521(7) Uani d . 1
H H5 0.0352 0.3051 0.9852 0.063 Uiso calc R 1
C C6 0.2215(4) 0.3096(2) 1.0897(2) 0.0588(8) Uani d . 1
H H6 0.1819 0.3315 1.1322 0.071 Uiso calc R 1
C C7 0.3821(3) 0.25763(16) 1.02174(17) 0.0444(6) Uani d . 1
C C8 0.5277(4) 0.2251(2) 1.0070(2) 0.0699(10) Uani d . 1
H H8A 0.5976 0.2116 1.0610 0.105 Uiso calc R 1
H H8B 0.5784 0.2609 0.9788 0.105 Uiso calc R 1
H H8C 0.5017 0.1815 0.9717 0.105 Uiso calc R 1
C C9 0.3097(3) 0.34777(15) 0.78098(17) 0.0381(6) Uani d . 1
C C10 0.4314(3) 0.40035(15) 0.76376(17) 0.0397(6) Uani d . 1
C C11 0.5341(4) 0.37354(18) 0.7172(2) 0.0581(8) Uani d . 1
H H11 0.5226 0.3250 0.6964 0.070 Uiso calc R 1
C C12 0.6531(4) 0.4179(2) 0.7015(2) 0.0695(11) Uani d . 1
H H12 0.7201 0.3994 0.6699 0.083 Uiso calc R 1
C C13 0.6715(4) 0.4893(2) 0.7328(2) 0.0679(10) Uani d . 1
H H13 0.7528 0.5189 0.7236 0.081 Uiso calc R 1
C C14 0.5691(4) 0.51740(18) 0.7781(2) 0.0558(8) Uani d . 1
H H14 0.5817 0.5662 0.7981 0.067 Uiso calc R 1
C C15 0.4473(3) 0.47388(15) 0.79433(17) 0.0398(6) Uani d . 1
C C16 0.3490(3) 0.50494(15) 0.84949(17) 0.0409(6) Uani d . 1
C C17 0.3339(4) 0.46496(17) 0.92179(19) 0.0540(8) Uani d . 1
H H17 0.3793 0.4179 0.9322 0.065 Uiso calc R 1
C C18 0.2531(5) 0.4938(2) 0.9781(2) 0.0700(10) Uani d . 1
H H18 0.2425 0.4659 1.0249 0.084 Uiso calc R 1
C C19 0.1889(5) 0.5637(2) 0.9645(2) 0.0805(12) Uani d . 1
H H19 0.1351 0.5834 1.0024 0.097 Uiso calc R 1
C C20 0.2040(5) 0.60497(19) 0.8946(2) 0.0682(10) Uani d . 1
H H20 0.1615 0.6527 0.8863 0.082 Uiso calc R 1
C C21 0.2815(3) 0.57618(15) 0.83676(17) 0.0429(6) Uani d . 1
C C22 0.2822(3) 0.62358(15) 0.75948(18) 0.0414(6) Uani d . 1
N N1 0.2424(3) 0.26251(13) 0.96545(14) 0.0411(5) Uani d . 1
N N2 0.3718(3) 0.28605(15) 1.09724(15) 0.0528(6) Uani d . 1
H H2 0.4479 0.2889 1.1429 0.063 Uiso calc R 1
N N3 -0.0259(2) 0.20308(13) 0.84973(13) 0.0394(5) Uani d . 1
N N4 -0.2186(3) 0.15028(15) 0.89015(16) 0.0530(6) Uani d . 1
H H4A -0.2689 0.1201 0.9152 0.064 Uiso calc R 1
O O1 0.1663(2) 0.36111(11) 0.75780(13) 0.0527(5) Uani d U 1
O O2 0.3644(2) 0.28816(10) 0.82080(11) 0.0399(4) Uani d . 1
O O1W -0.3240(3) 0.03831(16) 0.9770(2) 0.0705(7) Uani d D 1
O O3 0.2146(3) 0.60283(11) 0.68615(13) 0.0564(5) Uani d . 1
O O2W 0.0770(3) 0.46838(15) 0.63200(15) 0.0693(7) Uani d D 1
O O4 0.3503(2) 0.68677(10) 0.77385(11) 0.0412(4) Uani d . 1
Cu Cu1 0.18444(3) 0.234302(17) 0.841723(19) 0.03370(10) Uani d . 1
H HW11 -0.343(4) 0.040(2) 1.0252(14) 0.092(15) Uiso d D 1
H HW12 -0.387(3) 0.0107(17) 0.9426(16) 0.067(12) Uiso d D 1
H HW21 0.098(4) 0.4360(15) 0.6711(19) 0.085(13) Uiso d D 1
H HW22 0.117(5) 0.5101(13) 0.653(2) 0.104(16) 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'
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_3
_geom_angle
_geom_angle_publ_flag
N3 C1 N4 . 109.4(2) ?
N3 C1 C2 . 127.1(3) ?
N4 C1 C2 . 123.6(3) ?
C1 C2 H2A . 109.5 ?
C1 C2 H2B . 109.5 ?
H2A C2 H2B . 109.5 ?
C1 C2 H2C . 109.5 ?
H2A C2 H2C . 109.5 ?
H2B C2 H2C . 109.5 ?
C4 C3 N4 . 105.8(3) ?
C4 C3 H3 . 127.1 ?
N4 C3 H3 . 127.1 ?
C3 C4 N3 . 109.5(3) ?
C3 C4 H4 . 125.3 ?
N3 C4 H4 . 125.3 ?
C6 C5 N1 . 109.3(3) ?
C6 C5 H5 . 125.4 ?
N1 C5 H5 . 125.4 ?
C5 C6 N2 . 106.3(3) ?
C5 C6 H6 . 126.8 ?
N2 C6 H6 . 126.8 ?
N1 C7 N2 . 109.4(3) ?
N1 C7 C8 . 126.9(3) ?
N2 C7 C8 . 123.7(3) ?
C7 C8 H8A . 109.5 ?
C7 C8 H8B . 109.5 ?
H8A C8 H8B . 109.5 ?
C7 C8 H8C . 109.5 ?
H8A C8 H8C . 109.5 ?
H8B C8 H8C . 109.5 ?
O1 C9 O2 . 122.4(2) ?
O1 C9 C10 . 122.4(2) ?
O2 C9 C10 . 115.3(2) ?
C11 C10 C15 . 119.5(3) ?
C11 C10 C9 . 117.9(3) ?
C15 C10 C9 . 122.6(2) ?
C12 C11 C10 . 121.2(3) ?
C12 C11 H11 . 119.4 ?
C10 C11 H11 . 119.4 ?
C13 C12 C11 . 119.6(3) ?
C13 C12 H12 . 120.2 ?
C11 C12 H12 . 120.2 ?
C12 C13 C14 . 120.1(3) ?
C12 C13 H13 . 119.9 ?
C14 C13 H13 . 119.9 ?
C13 C14 C15 . 121.4(3) ?
C13 C14 H14 . 119.3 ?
C15 C14 H14 . 119.3 ?
C14 C15 C10 . 118.2(3) ?
C14 C15 C16 . 119.0(3) ?
C10 C15 C16 . 122.6(2) ?
C21 C16 C17 . 117.6(2) ?
C21 C16 C15 . 122.6(2) ?
C17 C16 C15 . 119.6(3) ?
C18 C17 C16 . 121.6(3) ?
C18 C17 H17 . 119.2 ?
C16 C17 H17 . 119.2 ?
C19 C18 C17 . 119.7(3) ?
C19 C18 H18 . 120.1 ?
C17 C18 H18 . 120.1 ?
C18 C19 C20 . 120.0(3) ?
C18 C19 H19 . 120.0 ?
C20 C19 H19 . 120.0 ?
C19 C20 C21 . 120.9(3) ?
C19 C20 H20 . 119.5 ?
C21 C20 H20 . 119.5 ?
C20 C21 C16 . 120.2(3) ?
C20 C21 C22 . 116.8(3) ?
C16 C21 C22 . 123.0(2) ?
O3 C22 O4 . 122.0(2) ?
O3 C22 C21 . 121.2(3) ?
O4 C22 C21 . 116.8(2) ?
C7 N1 C5 . 106.2(2) ?
C7 N1 Cu1 . 128.57(19) ?
C5 N1 Cu1 . 125.17(19) ?
C7 N2 C6 . 108.8(3) ?
C7 N2 H2 . 125.6 ?
C6 N2 H2 . 125.6 ?
C1 N3 C4 . 106.5(2) ?
C1 N3 Cu1 . 128.17(19) ?
C4 N3 Cu1 . 125.1(2) ?
C1 N4 C3 . 108.9(2) ?
C1 N4 H4A . 125.6 ?
C3 N4 H4A . 125.6 ?
C9 O2 Cu1 . 106.61(16) ?
HW11 O1W HW12 . 112(3) ?
HW21 O2W HW22 . 109(3) ?
C22 O4 Cu1 2_556 104.84(16) ?
O2 Cu1 N3 . 165.28(8) y
O2 Cu1 N1 . 91.99(9) y
N3 Cu1 N1 . 90.72(9) y
O2 Cu1 O4 2_546 89.39(8) y
N3 Cu1 O4 2_546 90.88(9) y
N1 Cu1 O4 2_546 168.31(8) y
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
C1 N3 . 1.324(3) ?
C1 N4 . 1.340(3) ?
C1 C2 . 1.478(4) ?
C2 H2A . 0.96 ?
C2 H2B . 0.96 ?
C2 H2C . 0.96 ?
C3 C4 . 1.344(4) ?
C3 N4 . 1.363(4) ?
C3 H3 . 0.93 ?
C4 N3 . 1.376(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.343(4) ?
C5 N1 . 1.383(4) ?
C5 H5 . 0.93 ?
C6 N2 . 1.357(4) ?
C6 H6 . 0.93 ?
C7 N1 . 1.328(4) ?
C7 N2 . 1.343(3) ?
C7 C8 . 1.475(4) ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 O1 . 1.240(3) ?
C9 O2 . 1.276(3) ?
C9 C10 . 1.500(4) ?
C10 C11 . 1.395(4) ?
C10 C15 . 1.403(4) ?
C11 C12 . 1.384(5) ?
C11 H11 . 0.93 ?
C12 C13 . 1.371(5) ?
C12 H12 . 0.93 ?
C13 C14 . 1.386(5) ?
C13 H13 . 0.93 ?
C14 C15 . 1.399(4) ?
C14 H14 . 0.93 ?
C15 C16 . 1.493(4) ?
C16 C21 . 1.401(4) ?
C16 C17 . 1.403(4) ?
C17 C18 . 1.384(4) ?
C17 H17 . 0.93 ?
C18 C19 . 1.369(5) ?
C18 H18 . 0.93 ?
C19 C20 . 1.383(4) ?
C19 H19 . 0.93 ?
C20 C21 . 1.384(4) ?
C20 H20 . 0.93 ?
C21 C22 . 1.509(4) ?
C22 O3 . 1.238(3) ?
C22 O4 . 1.274(3) ?
Cu1 N1 . 1.994(2) y
N2 H2 . 0.86 ?
Cu1 N3 . 1.960(2) y
N4 H4A . 0.86 ?
Cu1 O2 . 1.9488(17) y
O1W HW11 . 0.837(17) ?
O1W HW12 . 0.840(17) ?
O2W HW21 . 0.842(17) ?
O2W HW22 . 0.859(18) ?
O4 Cu1 2_556 2.0005(18) ?
Cu1 O4 2_546 2.0005(18) y
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 HW12 O2W 2_446 0.840(17) 1.94(2) 2.757(4) 163(3)
O1W HW11 O2W 4_566 0.837(17) 2.02(2) 2.846(4) 169(3)
O2W HW21 O1 . 0.842(17) 1.922(18) 2.761(3) 174(4)
O2W HW22 O3 . 0.859(18) 1.884(18) 2.738(3) 173(4)
N2 H2 O4 3_667 0.86 1.98 2.814(3) 164
N4 H4A O1W . 0.86 1.90 2.738(4) 163
