#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/72/2017290.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_2017290
loop_
_publ_author_name
'Wei, Linheng'
'Wang, Ziliang'
'Meng, Xianggao'
_publ_section_title
;
 Three-dimensional networks in bis(imidazolium) 2,2'-dithiodibenzoate
 and 4-methylimidazolium 2-[(2-carboxyphenyl)disulfanyl]benzoate
;
_journal_coeditor_code           FG3123
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o453
_journal_page_last               o456
_journal_paper_doi               10.1107/S0108270109030686
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '2C3 H5 N2 + , C14 H8 O4 S2 2-'
_chemical_formula_moiety         '2C3 H5 N2 + , C14 H8 O4 S2 2-'
_chemical_formula_sum            'C20 H18 N4 O4 S2'
_chemical_formula_weight         442.50
_chemical_name_systematic
;
bis(imidazolium) 2,2'-dithiodibenzoate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.2280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.0142(13)
_cell_length_b                   5.9064(4)
_cell_length_c                   19.9254(15)
_cell_measurement_reflns_used    2506
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.44
_cell_measurement_theta_min      2.40
_cell_volume                     1996.9(3)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.3° wide ω exposures'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed Siemens Mo tube'
_diffrn_radiation_type           'Mo k\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10805
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_correction_T_min  0.9045
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0461
_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)+(0.0702P)²+0.7582P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                1721
_reflns_number_total             2283
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg3123.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2017290
_cod_database_fobs_code          2017290
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.48149(3) 0.04094(10) 0.69993(3) 0.0397(2) Uani d . 1 . .
O O1 0.30395(8) 0.0444(3) 0.53687(7) 0.0412(4) Uani d . 1 . .
O O2 0.43265(8) 0.0302(3) 0.56336(7) 0.0417(4) Uani d . 1 . .
C C1 0.35552(11) 0.2582(3) 0.63087(9) 0.0325(5) Uani d . 1 . .
C C2 0.40456(11) 0.2497(3) 0.69097(10) 0.0338(5) Uani d . 1 . .
C C3 0.39232(14) 0.4048(4) 0.74170(10) 0.0457(6) Uani d . 1 . .
H H3 0.4237 0.3988 0.7819 0.055 Uiso calc R 1 . .
C C4 0.33418(15) 0.5676(4) 0.73326(12) 0.0542(7) Uani d . 1 . .
H H4 0.3266 0.6693 0.7678 0.065 Uiso calc R 1 . .
C C5 0.28745(15) 0.5803(4) 0.67411(13) 0.0527(6) Uani d . 1 . .
H H5 0.2490 0.6920 0.6681 0.063 Uiso calc R 1 . .
C C6 0.29824(13) 0.4252(4) 0.62376(11) 0.0412(5) Uani d . 1 . .
H H6 0.2662 0.4330 0.5840 0.049 Uiso calc R 1 . .
C C7 0.36484(11) 0.0979(3) 0.57310(9) 0.0308(4) Uani d . 1 . .
N N1 0.15372(10) 0.0371(3) 0.56232(9) 0.0392(4) Uani d . 1 . .
H H1 0.2020 0.0694 0.5562 0.047 Uiso calc R 1 . .
C C2' 0.11896(12) -0.1578(4) 0.54832(10) 0.0386(5) Uani d . 1 . .
H H2' 0.1423 -0.2833 0.5298 0.046 Uiso calc R 1 . .
N N3 0.04561(10) -0.1459(3) 0.56494(8) 0.0395(4) Uani d . 1 . .
H H3' 0.0114 -0.2531 0.5609 0.047 Uiso calc R 1 . .
C C4' 0.03301(13) 0.0661(4) 0.58975(11) 0.0412(5) Uani d . 1 . .
H H4' -0.0138 0.1207 0.6048 0.049 Uiso calc R 1 . .
C C5' 0.10054(13) 0.1795(4) 0.58818(11) 0.0423(5) Uani d . 1 . .
H H5' 0.1097 0.3280 0.6021 0.051 Uiso calc R 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
C2 S1 S1 . 2_656 105.44(7) ?
C6 C1 C2 . . 118.69(18) ?
C6 C1 C7 . . 118.77(17) ?
C2 C1 C7 . . 122.51(18) ?
C3 C2 C1 . . 118.88(19) ?
C3 C2 S1 . . 121.77(16) ?
C1 C2 S1 . . 119.34(15) ?
C4 C3 C2 . . 121.0(2) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C5 C4 C3 . . 120.4(2) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 C6 . . 119.2(2) ?
C4 C5 H5 . . 120.4 ?
C6 C5 H5 . . 120.4 ?
C5 C6 C1 . . 121.8(2) ?
C5 C6 H6 . . 119.1 ?
C1 C6 H6 . . 119.1 ?
O2 C7 O1 . . 124.11(18) ?
O2 C7 C1 . . 118.02(16) ?
O1 C7 C1 . . 117.85(17) ?
C2' N1 C5' . . 108.63(18) ?
C2' N1 H1 . . 125.7 ?
C5' N1 H1 . . 125.7 ?
N1 C2' N3 . . 108.64(19) ?
N1 C2' H2' . . 125.7 ?
N3 C2' H2' . . 125.7 ?
C2' N3 C4' . . 108.45(19) ?
C2' N3 H3' . . 125.8 ?
C4' N3 H3' . . 125.8 ?
C5' C4' N3 . . 107.03(18) ?
C5' C4' H4' . . 126.5 ?
N3 C4' H4' . . 126.5 ?
C4' C5' N1 . . 107.2(2) ?
C4' C5' H5' . . 126.4 ?
N1 C5' H5' . . 126.4 ?
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
S1 C2 . 1.798(2) ?
S1 S1 2_656 2.0476(10) ?
O1 C7 . 1.259(2) ?
O2 C7 . 1.250(2) ?
C1 C6 . 1.387(3) ?
C1 C2 . 1.409(3) ?
C1 C7 . 1.508(3) ?
C2 C3 . 1.391(3) ?
C3 C4 . 1.381(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.374(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
N1 C2' . 1.315(3) ?
N1 C5' . 1.364(3) ?
N1 H1 . 0.8600 ?
C2' N3 . 1.316(3) ?
C2' H2' . 0.9300 ?
N3 C4' . 1.369(3) ?
N3 H3' . 0.8600 ?
C4' C5' . 1.332(3) ?
C4' H4' . 0.9300 ?
C5' H5' . 0.9300 ?
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
_geom_hbond_publ_flag
N1 H1 O1 . 0.86 1.81 2.643(2) 162 yes
N3 H3' O2 3_445 0.86 1.86 2.710(2) 172 yes
C2' H2' O1 7_546 0.93 2.27 3.185(3) 167 yes
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 . . . . 1.8(3) ?
C7 C1 C2 C3 . . . . 179.61(19) ?
C6 C1 C2 S1 . . . . -177.77(15) ?
C7 C1 C2 S1 . . . . 0.0(3) ?
S1 S1 C2 C3 2_656 . . . 13.6(2) ?
S1 S1 C2 C1 2_656 . . . -166.81(15) ?
C1 C2 C3 C4 . . . . -1.2(3) ?
S1 C2 C3 C4 . . . . 178.38(19) ?
C2 C3 C4 C5 . . . . -0.4(4) ?
C3 C4 C5 C6 . . . . 1.4(4) ?
C4 C5 C6 C1 . . . . -0.7(4) ?
C2 C1 C6 C5 . . . . -0.9(3) ?
C7 C1 C6 C5 . . . . -178.8(2) ?
C6 C1 C7 O2 . . . . 145.2(2) ?
C2 C1 C7 O2 . . . . -32.6(3) ?
C6 C1 C7 O1 . . . . -33.3(3) ?
C2 C1 C7 O1 . . . . 148.9(2) ?
C5' N1 C2' N3 . . . . -0.6(2) ?
N1 C2' N3 C4' . . . . 0.7(2) ?
C2' N3 C4' C5' . . . . -0.6(2) ?
N3 C4' C5' N1 . . . . 0.2(2) ?
C2' N1 C5' C4' . . . . 0.3(2) ?
