#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/07/2230790.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_2230790
loop_
_publ_author_name
'Dong, Gui-Ying'
'Liu, Tong-Fei'
'He, Cui-Hong'
'Deng, Xiao-Chen'
'Shi, Xiao-Ge'
_publ_section_title
;
 1,1'-[1,4-Phenylenebis(methylene)]bis(2-methyl-1H-imidazol-3-ium)
 2,4-dicarboxybenzene-1,5-dicarboxylate monohydrate
;
_journal_coeditor_code           LH5268
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1696
_journal_paper_doi               10.1107/S160053681102263X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H20 N4 2+, C10 H4 O8 2-, H2 O'
_chemical_formula_moiety         'C16 H20 N4 2+, C10 H4 O8 2-, H2 O'
_chemical_formula_sum            'C26 H26 N4 O9'
_chemical_formula_weight         538.51
_chemical_name_systematic
;
1,1'-[1,4-Phenylenebis(methylene)]bis(2-methyl-1H-imidazol-3-ium)
2,4-dicarboxybenzene-1,5-dicarboxylate monohydrate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.39(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7139(19)
_cell_length_b                   19.428(4)
_cell_length_c                   13.856(3)
_cell_measurement_reflns_used    2963
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.54
_cell_measurement_theta_min      4.58
_cell_volume                     2593.2(9)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0781
_diffrn_reflns_av_sigmaI/netI    0.0609
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20668
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0725
_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)+(0.0452P)²+1.9004P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1435
_reflns_number_gt                3075
_reflns_number_total             4571
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5268.cif
_cod_data_source_block           I
_cod_original_cell_volume        2593.3(9)
_cod_original_sg_symbol_H-M      ' P 21/c'
_cod_database_code               2230790
_cod_database_fobs_code          2230790
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.3527(2) 0.26814(12) 0.7753(2) 0.0460(7) Uani d . 1 1 . .
H H1 1.4361 0.2598 0.7806 0.069 Uiso calc R 1 1 . .
C C1 1.1278(3) 0.21981(14) 0.7695(2) 0.0211(7) Uani d . 1 1 . .
O O6 0.6182(2) 0.25426(12) 0.78948(16) 0.0389(6) Uani d . 1 1 . .
N N2 0.0283(3) 0.27283(15) 1.00182(19) 0.0370(7) Uani d . 1 1 . .
C C6 1.0713(3) 0.28578(15) 0.7517(2) 0.0241(7) Uani d . 1 1 . .
H H6 1.1309 0.3232 0.7512 0.029 Uiso calc R 1 1 . .
C C5 0.9277(3) 0.29696(14) 0.7346(2) 0.0215(7) Uani d . 1 1 . .
C C2 1.0382(3) 0.16286(15) 0.7718(2) 0.0228(7) Uani d . 1 1 . .
O O3 1.0942(3) 0.04591(11) 0.73740(17) 0.0466(7) Uani d . 1 1 . .
C C10 0.8718(3) 0.36897(15) 0.7201(2) 0.0280(7) Uani d . 1 1 . .
O O7 0.7529(2) 0.38125(12) 0.6872(2) 0.0552(8) Uani d . 1 1 . .
C C4 0.8365(3) 0.23966(15) 0.7314(2) 0.0211(7) Uani d . 1 1 . .
C C9 0.6773(3) 0.24479(15) 0.7138(2) 0.0280(7) Uani d . 1 1 . .
C C3 0.8944(3) 0.17407(15) 0.7510(2) 0.0251(7) Uani d . 1 1 . .
H H3 0.8351 0.1364 0.7501 0.030 Uiso calc R 1 1 . .
N N3 0.4318(3) 0.51795(13) 0.63373(19) 0.0311(7) Uani d . 1 1 . .
O O5 0.6155(2) 0.23446(14) 0.62994(17) 0.0487(7) Uani d . 1 1 . .
N N1 0.2118(3) 0.33609(14) 1.03805(19) 0.0341(7) Uani d . 1 1 . .
C C7 1.2841(3) 0.21099(16) 0.7850(2) 0.0269(7) Uani d . 1 1 . .
O O4 1.1014(3) 0.07904(12) 0.89343(18) 0.0526(7) Uani d . 1 1 . .
C C18 0.0723(4) 0.33800(18) 1.0185(2) 0.0359(8) Uani d . 1 1 . .
O O2 1.3390(2) 0.15570(12) 0.8038(2) 0.0622(9) Uani d . 1 1 . .
C C8 1.0850(3) 0.08958(16) 0.8028(3) 0.0291(8) Uani d . 1 1 . .
C C14 0.4739(3) 0.47375(16) 0.8037(2) 0.0303(8) Uani d . 1 1 . .
O O8 0.9640(3) 0.41682(12) 0.7470(3) 0.0736(10) Uani d . 1 1 . .
H H8 0.9268 0.4547 0.7415 0.110 Uiso calc R 1 1 . .
C C23 0.3679(4) 0.47019(17) 0.5734(2) 0.0355(8) Uani d . 1 1 . .
C C25 0.3698(4) 0.58156(17) 0.6113(3) 0.0398(9) Uani d . 1 1 . .
H H25 0.3942 0.6232 0.6419 0.048 Uiso calc R 1 1 . .
C C17 0.3073(4) 0.39578(18) 1.0599(3) 0.0445(9) Uani d . 1 1 . .
H H17A 0.3840 0.3821 1.1079 0.053 Uiso calc R 1 1 . .
H H17B 0.2579 0.4327 1.0877 0.053 Uiso calc R 1 1 . .
C C11 0.3644(4) 0.42225(17) 0.9695(2) 0.0369(9) Uani d . 1 1 . .
N N4 0.2683(3) 0.50177(15) 0.5137(2) 0.0436(8) Uani d . 1 1 . .
C C22 0.5378(3) 0.50329(17) 0.7177(2) 0.0357(8) Uani d . 1 1 . .
H H22A 0.5868 0.5454 0.7377 0.043 Uiso calc R 1 1 . .
H H22B 0.6047 0.4708 0.6981 0.043 Uiso calc R 1 1 . .
C C19 0.1416(4) 0.22940(18) 1.0100(3) 0.0411(9) Uani d . 1 1 . .
H H19 0.1395 0.1819 1.0015 0.049 Uiso calc R 1 1 . .
C C20 0.2568(4) 0.26881(18) 1.0327(2) 0.0388(9) Uani d . 1 1 . .
H H20 0.3482 0.2535 1.0427 0.047 Uiso calc R 1 1 . .
C C13 0.5502(4) 0.4301(2) 0.8693(3) 0.0532(11) Uani d . 1 1 . .
H H13 0.6392 0.4174 0.8586 0.064 Uiso calc R 1 1 . .
C C24 0.2675(4) 0.57139(19) 0.5368(3) 0.0476(10) Uani d . 1 1 . .
H H24 0.2079 0.6047 0.5068 0.057 Uiso calc R 1 1 . .
C C16 0.2873(5) 0.4638(2) 0.9035(3) 0.0718(14) Uani d . 1 1 . .
H H16 0.1973 0.4755 0.9134 0.086 Uiso calc R 1 1 . .
C C12 0.4964(4) 0.4048(2) 0.9512(3) 0.0556(11) Uani d . 1 1 . .
H H12 0.5504 0.3758 0.9940 0.067 Uiso calc R 1 1 . .
C C15 0.3412(4) 0.4890(2) 0.8213(3) 0.0677(14) Uani d . 1 1 . .
H H15 0.2857 0.5167 0.7775 0.081 Uiso calc R 1 1 . .
O O1W 0.7588(2) 0.24523(16) 0.97416(18) 0.0651(9) Uani d . 1 1 . .
C C26 0.4009(4) 0.39518(18) 0.5750(3) 0.0522(11) Uani d . 1 1 . .
H H26A 0.3520 0.3725 0.6219 0.078 Uiso calc R 1 1 . .
H H26B 0.4990 0.3889 0.5923 0.078 Uiso calc R 1 1 . .
H H26C 0.3731 0.3759 0.5117 0.078 Uiso calc R 1 1 . .
C C21 -0.0224(4) 0.3989(2) 1.0153(3) 0.0587(11) Uani d . 1 1 . .
H H21A -0.0020 0.4250 1.0742 0.088 Uiso calc R 1 1 . .
H H21B -0.1170 0.3835 1.0089 0.088 Uiso calc R 1 1 . .
H H21C -0.0089 0.4274 0.9606 0.088 Uiso calc R 1 1 . .
H H1C 0.2174 0.4787 0.4575 0.088 Uiso d R 1 1 . .
H H2 -0.0820 0.2658 0.9924 0.088 Uiso d R 1 1 . .
H H1A 0.7048 0.2485 0.9205 0.088 Uiso d R 1 1 . .
H H1B 0.6895 0.2529 1.0044 0.088 Uiso d R 1 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'
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
C7 O1 H1 . . 109.5 ?
C6 C1 C2 . . 119.5(3) ?
C6 C1 C7 . . 119.4(3) ?
C2 C1 C7 . . 121.2(3) ?
C18 N2 C19 . . 109.2(3) ?
C18 N2 H2 . . 115.5 ?
C19 N2 H2 . . 134.9 ?
C5 C6 C1 . . 122.0(3) ?
C5 C6 H6 . . 119.0 ?
C1 C6 H6 . . 119.0 ?
C6 C5 C4 . . 119.2(3) ?
C6 C5 C10 . . 120.1(3) ?
C4 C5 C10 . . 120.8(2) ?
C3 C2 C1 . . 118.2(3) ?
C3 C2 C8 . . 116.8(2) ?
C1 C2 C8 . . 124.8(3) ?
O7 C10 O8 . . 123.5(3) ?
O7 C10 C5 . . 123.0(3) ?
O8 C10 C5 . . 113.5(3) ?
C3 C4 C5 . . 118.2(3) ?
C3 C4 C9 . . 117.3(3) ?
C5 C4 C9 . . 124.4(2) ?
O5 C9 O6 . . 125.1(3) ?
O5 C9 C4 . . 119.2(3) ?
O6 C9 C4 . . 115.4(3) ?
C4 C3 C2 . . 122.9(3) ?
C4 C3 H3 . . 118.6 ?
C2 C3 H3 . . 118.6 ?
C23 N3 C25 . . 108.8(3) ?
C23 N3 C22 . . 125.1(3) ?
C25 N3 C22 . . 125.7(3) ?
C18 N1 C20 . . 109.4(3) ?
C18 N1 C17 . . 127.0(3) ?
C20 N1 C17 . . 123.6(3) ?
O2 C7 O1 . . 123.9(3) ?
O2 C7 C1 . . 122.4(3) ?
O1 C7 C1 . . 113.8(3) ?
N2 C18 N1 . . 107.3(3) ?
N2 C18 C21 . . 124.0(3) ?
N1 C18 C21 . . 128.8(3) ?
O3 C8 O4 . . 126.8(3) ?
O3 C8 C2 . . 118.0(3) ?
O4 C8 C2 . . 115.0(3) ?
C15 C14 C13 . . 116.7(3) ?
C15 C14 C22 . . 122.9(3) ?
C13 C14 C22 . . 120.4(3) ?
C10 O8 H8 . . 109.5 ?
N4 C23 N3 . . 107.9(3) ?
N4 C23 C26 . . 126.4(3) ?
N3 C23 C26 . . 125.7(3) ?
C24 C25 N3 . . 107.1(3) ?
C24 C25 H25 . . 126.4 ?
N3 C25 H25 . . 126.4 ?
N1 C17 C11 . . 112.2(3) ?
N1 C17 H17A . . 109.2 ?
C11 C17 H17A . . 109.2 ?
N1 C17 H17B . . 109.2 ?
C11 C17 H17B . . 109.2 ?
H17A C17 H17B . . 107.9 ?
C16 C11 C12 . . 117.6(3) ?
C16 C11 C17 . . 121.5(3) ?
C12 C11 C17 . . 120.9(3) ?
C23 N4 C24 . . 109.2(3) ?
C23 N4 H1C . . 122.3 ?
C24 N4 H1C . . 127.8 ?
N3 C22 C14 . . 112.0(3) ?
N3 C22 H22A . . 109.2 ?
C14 C22 H22A . . 109.2 ?
N3 C22 H22B . . 109.2 ?
C14 C22 H22B . . 109.2 ?
H22A C22 H22B . . 107.9 ?
C20 C19 N2 . . 107.4(3) ?
C20 C19 H19 . . 126.3 ?
N2 C19 H19 . . 126.3 ?
C19 C20 N1 . . 106.8(3) ?
C19 C20 H20 . . 126.6 ?
N1 C20 H20 . . 126.6 ?
C14 C13 C12 . . 121.6(3) ?
C14 C13 H13 . . 119.2 ?
C12 C13 H13 . . 119.2 ?
C25 C24 N4 . . 107.0(3) ?
C25 C24 H24 . . 126.5 ?
N4 C24 H24 . . 126.5 ?
C11 C16 C15 . . 121.3(4) ?
C11 C16 H16 . . 119.4 ?
C15 C16 H16 . . 119.4 ?
C11 C12 C13 . . 121.0(4) ?
C11 C12 H12 . . 119.5 ?
C13 C12 H12 . . 119.5 ?
C14 C15 C16 . . 121.7(4) ?
C14 C15 H15 . . 119.1 ?
C16 C15 H15 . . 119.1 ?
H1A O1W H1B . . 88.8 ?
C23 C26 H26A . . 109.5 ?
C23 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C23 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C18 C21 H21A . . 109.5 ?
C18 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C18 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
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
O1 C7 . 1.311(4) ?
O1 H1 . 0.8200 ?
C1 C6 . 1.404(4) ?
C1 C2 . 1.411(4) ?
C1 C7 . 1.516(4) ?
O6 C9 . 1.272(4) ?
N2 C18 . 1.347(4) ?
N2 C19 . 1.380(4) ?
N2 H2 . 1.0718 ?
C6 C5 . 1.402(4) ?
C6 H6 . 0.9300 ?
C5 C4 . 1.420(4) ?
C5 C10 . 1.505(4) ?
C2 C3 . 1.406(4) ?
C2 C8 . 1.539(4) ?
O3 C8 . 1.253(4) ?
C10 O7 . 1.210(4) ?
C10 O8 . 1.312(4) ?
C4 C3 . 1.405(4) ?
C4 C9 . 1.538(4) ?
C9 O5 . 1.253(4) ?
C3 H3 . 0.9300 ?
N3 C23 . 1.346(4) ?
N3 C25 . 1.392(4) ?
N3 C22 . 1.479(4) ?
N1 C18 . 1.349(4) ?
N1 C20 . 1.383(4) ?
N1 C17 . 1.492(4) ?
C7 O2 . 1.212(4) ?
O4 C8 . 1.262(4) ?
C18 C21 . 1.496(5) ?
C14 C15 . 1.374(5) ?
C14 C13 . 1.386(5) ?
C14 C22 . 1.524(5) ?
O8 H8 . 0.8200 ?
C23 N4 . 1.338(4) ?
C23 C26 . 1.492(5) ?
C25 C24 . 1.352(5) ?
C25 H25 . 0.9300 ?
C17 C11 . 1.523(5) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C11 C16 . 1.369(5) ?
C11 C12 . 1.381(5) ?
N4 C24 . 1.390(4) ?
N4 H1C . 0.9761 ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
C19 C20 . 1.359(5) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C13 C12 . 1.398(5) ?
C13 H13 . 0.9300 ?
C24 H24 . 0.9300 ?
C16 C15 . 1.402(5) ?
C16 H16 . 0.9300 ?
C12 H12 . 0.9300 ?
C15 H15 . 0.9300 ?
O1W H1A . 0.8558 ?
O1W H1B . 0.8509 ?
C26 H26A . 0.9600 ?
C26 H26B . 0.9600 ?
C26 H26C . 0.9600 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
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
O1 H1 O6 1_655 0.82 1.76 2.575(3) 172
O1W H1A O6 1_555 0.86 1.90 2.747(3) 168
O1W H1B O5 4_566 0.85 1.98 2.743(3) 149
N4 H1C O4 4_465 0.98 1.75 2.679(4) 158
N2 H2 O1W 1_455 1.07 1.59 2.651(4) 172
O8 H8 O3 2_756 0.82 1.81 2.586(3) 157
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656786
