#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/53/2235318.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_2235318
loop_
_publ_author_name
'Wang, Yu-feng'
_publ_section_title
;
 Bis(2-methyl-1H-imidazol-3-ium) naphthalene-1,5-disulfonate
 dihydrate
;
_journal_coeditor_code           YK2053
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1619
_journal_paper_doi               10.1107/S1600536812019149
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '2C4 H7 N2 +, C10 H6 O6 S2 2-, 2H2 O'
_chemical_formula_moiety         '2(C4 H7 N2 +), C10 H6 O6 S2 2-, 2(H2 O)'
_chemical_formula_sum            'C18 H24 N4 O8 S2'
_chemical_formula_weight         488.53
_chemical_name_systematic
;
Bis(2-methyl-1H-imidazol-3-ium) naphthalene-1,5-disulfonate 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                75.58(3)
_cell_angle_beta                 75.10(3)
_cell_angle_gamma                80.34(3)
_cell_formula_units_Z            1
_cell_length_a                   7.1301(14)
_cell_length_b                   8.1773(16)
_cell_length_c                   9.970(2)
_cell_measurement_reflns_used    3638
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     540.7(2)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       '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  0.0592
_diffrn_reflns_av_sigmaI/netI    0.1005
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5695
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.330
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0396P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1074
_reflns_number_gt                1490
_reflns_number_total             2475
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            yk2053.cif
_cod_data_source_block           I
_cod_database_code               2235318
_cod_database_fobs_code          2235318
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_symmetry_multiplicity
O O4 0.7815(4) 0.0540(4) 0.1408(3) 0.0873(9) Uani d D 1 1
C C9 0.7423(4) 0.6967(3) -0.0199(3) 0.0419(7) Uani d . 1 1
H H9A 0.8089 0.7809 -0.0115 0.050 Uiso calc R 1 1
S S1 0.13194(10) 0.66733(9) 0.23893(7) 0.0342(2) Uani d . 1 1
O O3 0.2455(3) 0.6595(2) 0.33926(19) 0.0438(5) Uani d . 1 1
O O2 0.1153(3) 0.8363(2) 0.1501(2) 0.0481(5) Uani d . 1 1
C C7 0.4534(3) 0.5560(3) 0.0451(2) 0.0255(5) Uani d . 1 1
C C6 0.2599(3) 0.5340(3) 0.1233(2) 0.0271(6) Uani d . 1 1
O O1 -0.0547(2) 0.6045(2) 0.3027(2) 0.0501(5) Uani d . 1 1
N N2 0.4574(3) 0.1263(3) 0.3230(2) 0.0410(6) Uani d . 1 1
H H2B 0.5580 0.0903 0.2647 0.049 Uiso calc R 1 1
N N1 0.2739(3) 0.2647(3) 0.4672(2) 0.0438(6) Uani d . 1 1
H H1D 0.2318 0.3366 0.5212 0.053 Uiso calc R 1 1
C C2 0.4508(4) 0.2493(3) 0.3875(3) 0.0342(6) Uani d . 1 1
C C8 0.5575(4) 0.6821(3) 0.0549(3) 0.0349(6) Uani d . 1 1
H H8A 0.4977 0.7567 0.1140 0.042 Uiso calc R 1 1
C C5 0.1658(4) 0.4121(3) 0.1091(3) 0.0375(7) Uani d . 1 1
H H5C 0.0378 0.4008 0.1597 0.045 Uiso calc R 1 1
C C3 0.2826(4) 0.0645(4) 0.3619(3) 0.0571(9) Uani d . 1 1
H H3A 0.2496 -0.0228 0.3308 0.069 Uiso calc R 1 1
C C1 0.6089(4) 0.3484(4) 0.3718(3) 0.0500(8) Uani d . 1 1
H H1A 0.6461 0.3283 0.4610 0.075 Uiso calc R 1 1
H H1B 0.5664 0.4669 0.3429 0.075 Uiso calc R 1 1
H H1C 0.7188 0.3156 0.3012 0.075 Uiso calc R 1 1
C C4 0.1682(5) 0.1513(4) 0.4521(3) 0.0565(9) Uani d . 1 1
H H4A 0.0386 0.1372 0.4970 0.068 Uiso calc R 1 1
H H4B 0.876(4) -0.014(4) 0.158(3) 0.083(13) Uiso d D 1 1
H H4C 0.796(4) 0.096(4) 0.056(2) 0.069(11) Uiso d D 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'
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
H4B O4 H4C . . 112(2)
C8 C9 C5 . 2_665 120.6(2)
C8 C9 H9A . . 119.7
C5 C9 H9A 2_665 . 119.7
O3 S1 O1 . . 113.33(12)
O3 S1 O2 . . 111.00(12)
O1 S1 O2 . . 112.51(12)
O3 S1 C6 . . 107.66(11)
O1 S1 C6 . . 106.15(12)
O2 S1 C6 . . 105.65(11)
C8 C7 C7 . 2_665 118.6(3)
C8 C7 C6 . . 123.1(2)
C7 C7 C6 2_665 . 118.3(3)
C5 C6 C7 . . 120.8(2)
C5 C6 S1 . . 117.62(19)
C7 C6 S1 . . 121.57(18)
C2 N2 C3 . . 109.9(2)
C2 N2 H2B . . 125.1
C3 N2 H2B . . 125.1
C2 N1 C4 . . 109.9(2)
C2 N1 H1D . . 125.1
C4 N1 H1D . . 125.1
N2 C2 N1 . . 106.4(2)
N2 C2 C1 . . 126.3(2)
N1 C2 C1 . . 127.3(2)
C9 C8 C7 . . 121.1(2)
C9 C8 H8A . . 119.5
C7 C8 H8A . . 119.5
C6 C5 C9 . 2_665 120.6(2)
C6 C5 H5C . . 119.7
C9 C5 H5C 2_665 . 119.7
C4 C3 N2 . . 106.8(3)
C4 C3 H3A . . 126.6
N2 C3 H3A . . 126.6
C2 C1 H1A . . 109.5
C2 C1 H1B . . 109.5
H1A C1 H1B . . 109.5
C2 C1 H1C . . 109.5
H1A C1 H1C . . 109.5
H1B C1 H1C . . 109.5
C3 C4 N1 . . 107.1(3)
C3 C4 H4A . . 126.5
N1 C4 H4A . . 126.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O4 H4B . 0.824(17)
O4 H4C . 0.816(16)
C9 C8 . 1.346(3)
C9 C5 2_665 1.382(3)
C9 H9A . 0.9300
S1 O3 . 1.4237(18)
S1 O1 . 1.4392(19)
S1 O2 . 1.4483(19)
S1 C6 . 1.761(2)
C7 C8 . 1.402(3)
C7 C7 2_665 1.410(4)
C7 C6 . 1.415(3)
C6 C5 . 1.345(3)
N2 C2 . 1.310(3)
N2 C3 . 1.351(3)
N2 H2B . 0.8600
N1 C2 . 1.311(3)
N1 C4 . 1.347(3)
N1 H1D . 0.8600
C2 C1 . 1.451(3)
C8 H8A . 0.9300
C5 C9 2_665 1.382(3)
C5 H5C . 0.9300
C3 C4 . 1.313(4)
C3 H3A . 0.9300
C1 H1A . 0.9600
C1 H1B . 0.9600
C1 H1C . 0.9600
C4 H4A . 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
O4 H4C O2 2_665 0.816(16) 1.952(19) 2.754(3) 167(3)
O4 H4B O2 1_645 0.824(17) 1.92(2) 2.730(3) 166(3)
N1 H1D O1 2_566 0.86 2.00 2.768(3) 148.8
N2 H2B O4 . 0.86 1.78 2.628(3) 169.1
