#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/84/2228481.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228481
loop_
_publ_author_name
'Liu, Zhengming'
'Liu, Qiang'
'Yuan, Limin'
'Liu, Wenlong'
_publ_section_title
;
 1,1'-(p-Phenylenedimethylidene)diimidazol-3-ium
 bis{2-[(2-carboxyphenyl)disulfanyl]benzoate} dihydrate
;
_journal_coeditor_code           NG5063
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3230
_journal_paper_doi               10.1107/S1600536810047021
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H16 N4 2+, 2C14 H9 O4 S2 -, 2H2 O'
_chemical_formula_moiety         'C14 H16 N4 2+, 2(C14 H9 O4 S2 -), 2(H2 O)'
_chemical_formula_sum            'C42 H38 N4 O10 S4'
_chemical_formula_weight         887.00
_chemical_name_systematic
;
1,1'-(p-Phenylenedimethylidene)diimidazol-3-ium
bis{2-[(2-carboxyphenyl)disulfanyl]benzoate} 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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.985(3)
_cell_angle_beta                 90.686(3)
_cell_angle_gamma                100.634(3)
_cell_formula_units_Z            1
_cell_length_a                   4.6776(11)
_cell_length_b                   12.201(3)
_cell_length_c                   18.850(4)
_cell_measurement_reflns_used    1975
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.544
_cell_measurement_theta_min      2.278
_cell_volume                     1002.9(4)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7640
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.8936
_exptl_absorpt_correction_T_min  0.8757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.236
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0676P)²+0.1163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                2720
_reflns_number_total             3708
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng5063.cif
_cod_data_source_block           I
_cod_database_code               2228481
_cod_database_fobs_code          2228481
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.9224(5) 0.7640(2) 0.21093(14) 0.0356(6) Uani d . 1 . .
C C2 0.9027(5) 0.6438(2) 0.19945(14) 0.0352(6) Uani d . 1 . .
C C3 1.0412(6) 0.5796(2) 0.14067(15) 0.0443(7) Uani d . 1 . .
H H3 1.0227 0.4990 0.1313 0.053 Uiso calc R 1 . .
C C4 1.2053(6) 0.6331(2) 0.09606(16) 0.0500(7) Uani d . 1 . .
H H4 1.2968 0.5885 0.0571 0.060 Uiso calc R 1 . .
C C5 1.2351(6) 0.7522(3) 0.10862(17) 0.0483(7) Uani d . 1 . .
H H5 1.3507 0.7889 0.0794 0.058 Uiso calc R 1 . .
C C6 1.0910(6) 0.8157(2) 0.16511(16) 0.0437(7) Uani d . 1 . .
H H6 1.1066 0.8958 0.1729 0.052 Uiso calc R 1 . .
C C7 0.7699(6) 0.8391(2) 0.27118(16) 0.0405(6) Uani d . 1 . .
C C8 0.5723(5) 0.1938(2) 0.13953(14) 0.0375(6) Uani d . 1 . .
C C9 0.5950(5) 0.3156(2) 0.15799(14) 0.0357(6) Uani d . 1 . .
C C10 0.4493(6) 0.3591(2) 0.11132(15) 0.0433(7) Uani d . 1 . .
H H10 0.4668 0.4399 0.1224 0.052 Uiso calc R 1 . .
C C11 0.2789(6) 0.2841(3) 0.04877(17) 0.0496(7) Uani d . 1 . .
H H11 0.1817 0.3148 0.0184 0.060 Uiso calc R 1 . .
C C12 0.2513(6) 0.1640(3) 0.03089(17) 0.0530(8) Uani d . 1 . .
H H12 0.1350 0.1135 -0.0110 0.064 Uiso calc R 1 . .
C C13 0.3991(6) 0.1202(2) 0.07623(16) 0.0461(7) Uani d . 1 . .
H H13 0.3825 0.0393 0.0642 0.055 Uiso calc R 1 . .
C C14 0.7222(6) 0.1414(2) 0.18676(16) 0.0445(7) Uani d . 1 . .
S S1 0.69255(16) 0.57314(5) 0.25775(4) 0.0440(2) Uani d . 1 . .
S S2 0.81448(17) 0.41403(6) 0.23901(4) 0.0461(2) Uani d . 1 . .
O O1 0.7530(4) 0.94073(15) 0.26811(11) 0.0504(5) Uani d . 1 . .
O O2 0.6751(5) 0.80190(17) 0.32150(12) 0.0636(6) Uani d . 1 . .
O O3 0.8747(5) 0.19838(17) 0.24241(13) 0.0676(7) Uani d . 1 . .
O O4 0.6690(6) 0.02564(17) 0.16259(13) 0.0670(7) Uani d D 1 . .
H H4A 0.737(8) 0.003(3) 0.1976(19) 0.100 Uiso d D 1 . .
C C15 0.3094(6) 0.1496(3) 0.35488(17) 0.0514(7) Uani d . 1 . .
H H15 0.3404 0.1817 0.3162 0.062 Uiso calc R 1 . .
C C16 0.3162(9) 0.0374(3) 0.4231(2) 0.0735(10) Uani d . 1 . .
H H16 0.3513 -0.0234 0.4398 0.088 Uiso calc R 1 . .
C C17 0.1658(8) 0.1195(3) 0.4573(2) 0.0731(11) Uani d . 1 . .
H H17 0.0816 0.1277 0.5026 0.088 Uiso calc R 1 . .
C C18 0.0401(6) 0.2974(2) 0.43199(18) 0.0513(7) Uani d . 1 . .
H H18A -0.1118 0.2936 0.4662 0.062 Uiso calc R 1 . .
H H18B -0.0463 0.3040 0.3868 0.062 Uiso calc R 1 . .
C C19 0.2748(5) 0.4039(2) 0.46723(14) 0.0406(6) Uani d D 1 . .
C C20 0.4029(7) 0.4741(3) 0.42709(17) 0.0623(9) Uani d D 1 . .
H H20 0.3376 0.4576 0.3774 0.075 Uiso calc R 1 . .
C C21 0.3731(7) 0.4311(3) 0.54080(16) 0.0656(9) Uani d D 1 . .
H H21 0.2879 0.3853 0.5692 0.079 Uiso calc R 1 . .
N N1 0.4076(5) 0.0579(2) 0.36030(15) 0.0512(6) Uani d D 1 . .
H H1 0.519(5) 0.016(2) 0.3270(14) 0.056(9) Uiso d D 1 . .
N N2 0.1594(5) 0.18873(19) 0.41342(13) 0.0466(6) Uani d . 1 . .
O O1W 0.2006(6) 0.7532(2) 0.40459(14) 0.0758(7) Uani d D 1 . .
H H1WA 0.351(5) 0.761(4) 0.378(2) 0.114 Uiso d D 1 . .
H H1WB 0.049(5) 0.747(4) 0.374(2) 0.114 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'
S S 0.1246 0.1234 '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
C6 C1 C2 . . 118.7(2) ?
C6 C1 C7 . . 118.9(2) ?
C2 C1 C7 . . 122.4(2) ?
C3 C2 C1 . . 118.8(2) ?
C3 C2 S1 . . 120.61(19) ?
C1 C2 S1 . . 120.52(19) ?
C4 C3 C2 . . 121.1(2) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 120.5(3) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 118.8(3) ?
C6 C5 H5 . . 120.6 ?
C4 C5 H5 . . 120.6 ?
C5 C6 C1 . . 122.0(2) ?
C5 C6 H6 . . 119.0 ?
C1 C6 H6 . . 119.0 ?
O2 C7 O1 . . 123.3(2) ?
O2 C7 C1 . . 119.2(2) ?
O1 C7 C1 . . 117.5(2) ?
C13 C8 C9 . . 119.1(2) ?
C13 C8 C14 . . 119.2(2) ?
C9 C8 C14 . . 121.7(2) ?
C10 C9 C8 . . 118.8(2) ?
C10 C9 S2 . . 120.34(19) ?
C8 C9 S2 . . 120.83(19) ?
C11 C10 C9 . . 120.9(3) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C12 C11 C10 . . 120.7(3) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C13 C12 C11 . . 118.8(3) ?
C13 C12 H12 . . 120.6 ?
C11 C12 H12 . . 120.6 ?
C12 C13 C8 . . 121.7(3) ?
C12 C13 H13 . . 119.2 ?
C8 C13 H13 . . 119.2 ?
O3 C14 O4 . . 122.8(3) ?
O3 C14 C8 . . 123.6(2) ?
O4 C14 C8 . . 113.6(3) ?
C2 S1 S2 . . 106.04(8) ?
C9 S2 S1 . . 105.87(8) ?
C14 O4 H4A . . 107(3) ?
N1 C15 N2 . . 109.0(3) ?
N1 C15 H15 . . 125.5 ?
N2 C15 H15 . . 125.5 ?
C17 C16 N1 . . 108.1(3) ?
C17 C16 H16 . . 125.9 ?
N1 C16 H16 . . 125.9 ?
C16 C17 N2 . . 107.0(3) ?
C16 C17 H17 . . 126.5 ?
N2 C17 H17 . . 126.5 ?
N2 C18 C19 . . 111.0(2) ?
N2 C18 H18A . . 109.4 ?
C19 C18 H18A . . 109.4 ?
N2 C18 H18B . . 109.4 ?
C19 C18 H18B . . 109.4 ?
H18A C18 H18B . . 108.0 ?
C20 C19 C21 . . 118.3(2) ?
C20 C19 C18 . . 121.7(2) ?
C21 C19 C18 . . 120.0(2) ?
C19 C20 C21 . 2_666 121.2(3) ?
C19 C20 H20 . . 119.4 ?
C21 C20 H20 2_666 . 119.4 ?
C19 C21 C20 . 2_666 120.5(3) ?
C19 C21 H21 . . 119.7 ?
C20 C21 H21 2_666 . 119.7 ?
C15 N1 C16 . . 108.1(3) ?
C15 N1 H1 . . 125.3(19) ?
C16 N1 H1 . . 126.6(19) ?
C15 N2 C17 . . 107.8(3) ?
C15 N2 C18 . . 125.6(3) ?
C17 N2 C18 . . 126.2(3) ?
H1WA O1W H1WB . . 104(3) ?
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 C6 . 1.391(3) ?
C1 C2 . 1.400(3) ?
C1 C7 . 1.502(4) ?
C2 C3 . 1.389(3) ?
C2 S1 . 1.793(3) ?
C3 C4 . 1.376(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.378(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.375(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O2 . 1.226(3) ?
C7 O1 . 1.276(3) ?
C8 C13 . 1.391(4) ?
C8 C9 . 1.400(3) ?
C8 C14 . 1.482(4) ?
C9 C10 . 1.389(4) ?
C9 S2 . 1.790(3) ?
C10 C11 . 1.380(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.379(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.378(4) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 O3 . 1.200(3) ?
C14 O4 . 1.317(3) ?
S1 S2 . 2.0515(10) ?
O4 H4A . 0.87(2) ?
C15 N1 . 1.316(4) ?
C15 N2 . 1.325(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.337(5) ?
C16 N1 . 1.342(4) ?
C16 H16 . 0.9300 ?
C17 N2 . 1.356(4) ?
C17 H17 . 0.9300 ?
C18 N2 . 1.478(3) ?
C18 C19 . 1.503(4) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 C20 . 1.374(3) ?
C19 C21 . 1.374(3) ?
C20 C21 2_666 1.381(3) ?
C20 H20 . 0.9300 ?
C21 C20 2_666 1.381(3) ?
C21 H21 . 0.9300 ?
N1 H1 . 0.911(17) ?
O1W H1WA . 0.876(18) ?
O1W H1WB . 0.883(18) ?
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 H1WB S1 1_455 0.883(18) 2.80(3) 3.507(3) 138(4)
O1W H1WB O2 1_455 0.883(18) 2.30(2) 3.141(4) 159(4)
N1 H1 O1 1_545 0.911(17) 1.748(18) 2.657(3) 176(3)
O4 H4A O1 1_545 0.87(2) 1.73(3) 2.567(3) 161(4)
O1W H1WA O2 . 0.876(18) 1.94(2) 2.811(3) 171(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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -2.9(4) ?
C7 C1 C2 C3 . . . . 177.6(2) ?
C6 C1 C2 S1 . . . . 179.13(19) ?
C7 C1 C2 S1 . . . . -0.4(3) ?
C1 C2 C3 C4 . . . . 2.6(4) ?
S1 C2 C3 C4 . . . . -179.4(2) ?
C2 C3 C4 C5 . . . . -0.2(4) ?
C3 C4 C5 C6 . . . . -1.9(4) ?
C4 C5 C6 C1 . . . . 1.6(4) ?
C2 C1 C6 C5 . . . . 0.8(4) ?
C7 C1 C6 C5 . . . . -179.6(3) ?
C6 C1 C7 O2 . . . . -164.2(3) ?
C2 C1 C7 O2 . . . . 15.3(4) ?
C6 C1 C7 O1 . . . . 13.9(4) ?
C2 C1 C7 O1 . . . . -166.5(2) ?
C13 C8 C9 C10 . . . . -1.6(4) ?
C14 C8 C9 C10 . . . . 179.9(2) ?
C13 C8 C9 S2 . . . . 179.85(19) ?
C14 C8 C9 S2 . . . . 1.4(3) ?
C8 C9 C10 C11 . . . . 1.6(4) ?
S2 C9 C10 C11 . . . . -179.8(2) ?
C9 C10 C11 C12 . . . . -0.5(4) ?
C10 C11 C12 C13 . . . . -0.6(4) ?
C11 C12 C13 C8 . . . . 0.6(4) ?
C9 C8 C13 C12 . . . . 0.5(4) ?
C14 C8 C13 C12 . . . . 179.1(3) ?
C13 C8 C14 O3 . . . . -179.7(3) ?
C9 C8 C14 O3 . . . . -1.2(4) ?
C13 C8 C14 O4 . . . . -0.7(4) ?
C9 C8 C14 O4 . . . . 177.8(2) ?
C3 C2 S1 S2 . . . . 16.6(2) ?
C1 C2 S1 S2 . . . . -165.39(19) ?
C10 C9 S2 S1 . . . . 16.4(2) ?
C8 C9 S2 S1 . . . . -165.10(18) ?
C2 S1 S2 C9 . . . . -84.96(12) ?
N1 C16 C17 N2 . . . . 1.7(4) ?
N2 C18 C19 C20 . . . . 100.9(3) ?
N2 C18 C19 C21 . . . . -77.0(3) ?
C21 C19 C20 C21 . . . 2_666 0.8(5) ?
C18 C19 C20 C21 . . . 2_666 -177.2(3) ?
C20 C19 C21 C20 . . . 2_666 -0.8(5) ?
C18 C19 C21 C20 . . . 2_666 177.2(3) ?
N2 C15 N1 C16 . . . . 0.6(4) ?
C17 C16 N1 C15 . . . . -1.5(4) ?
N1 C15 N2 C17 . . . . 0.5(4) ?
N1 C15 N2 C18 . . . . 173.2(2) ?
C16 C17 N2 C15 . . . . -1.4(4) ?
C16 C17 N2 C18 . . . . -174.1(3) ?
C19 C18 N2 C15 . . . . -78.1(3) ?
C19 C18 N2 C17 . . . . 93.3(4) ?
