##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Bis(3-methylanilinium) naphthalene-1,5-disulfonate
;
_chemical_name_common     ?
_chemical_formula_moiety     '2(C7 H10 N +), C10 H6 O6 S2 2-'
_chemical_formula_sum     'C24 H26 N2 O6 S2'
_chemical_formula_iupac     '2C7 H10 N +, C10 H6 O6 S2 2-'
_chemical_formula_weight     502.59
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     8.3426(17)
_cell_length_b     19.896(4)
_cell_length_c     7.0670(14)
_cell_angle_alpha     90.00
_cell_angle_beta     90.14(3)
_cell_angle_gamma     90.00
_cell_volume     1173.0(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2066
_cell_measurement_theta_min     3.36
_cell_measurement_theta_max     24.99
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.32
_exptl_crystal_size_min     0.28
_exptl_crystal_density_diffrn     1.423
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     528
_exptl_absorpt_coefficient_mu     0.271
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrystalClear; Rigaku, 2005)'
_exptl_absorpt_correction_T_min     0.901
_exptl_absorpt_correction_T_max     0.923
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku Mercury2'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     13.6612
_diffrn_reflns_number     10755
_diffrn_reflns_av_R_equivalents     0.0364
_diffrn_reflns_av_sigmaI/netI     0.0270
_diffrn_reflns_theta_min     3.06
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -24
_diffrn_reflns_limit_k_max     24
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     8
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2311
_reflns_number_gt     2131
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0865
_refine_ls_R_factor_gt     0.0822
_refine_ls_wR_factor_gt     0.1881
_refine_ls_wR_factor_ref     0.1896
_refine_ls_goodness_of_fit_ref     1.215
_refine_ls_restrained_S_all     1.215
_refine_ls_number_reflns     2311
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0077P)²+6.1071P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.034
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.501
_refine_diff_density_min     -0.326
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement     'CrystalClear (Rigaku, 2005)'
_computing_data_reduction     'CrystalClear (Rigaku, 2005)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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
    S S1 0.19559(14) 0.57953(6) 0.74214(17) 0.0295(3) Uani d . 1 1 . .
    O O2 0.2105(5) 0.6206(2) 0.9102(5) 0.0493(11) Uani d . 1 1 . .
    O O3 0.1516(5) 0.6197(2) 0.5795(6) 0.0518(11) Uani d . 1 1 . .
    O O1 0.0920(5) 0.5221(2) 0.7674(7) 0.0554(12) Uani d . 1 1 . .
    N N1 1.0108(5) 0.6117(2) 0.2234(6) 0.0388(10) Uani d . 1 1 . .
    H H1A 1.0688 0.6144 0.3290 0.058 Uiso calc R 1 1 . .
    H H1B 1.0748 0.6160 0.1236 0.058 Uiso calc R 1 1 . .
    H H1C 0.9618 0.5720 0.2189 0.058 Uiso calc R 1 1 . .
    C C11 0.3285(6) 0.4582(3) 0.2293(7) 0.0360(12) Uani d . 1 1 . .
    H H11 0.2464 0.4479 0.1447 0.043 Uiso calc R 1 1 . .
    C C8 0.3919(5) 0.5474(2) 0.6913(7) 0.0288(10) Uani d . 1 1 . .
    C C9 0.4199(5) 0.5100(2) 0.5201(6) 0.0265(10) Uani d . 1 1 . .
    C C7 0.7308(6) 0.6503(3) 0.2401(7) 0.0334(11) Uani d . 1 1 . .
    H H7 0.6988 0.6057 0.2505 0.040 Uiso calc R 1 1 . .
    C C10 0.2950(6) 0.4918(2) 0.3920(7) 0.0317(11) Uani d . 1 1 . .
    H H10 0.1895 0.5031 0.4200 0.038 Uiso calc R 1 1 . .
    C C6 0.8907(6) 0.6655(3) 0.2215(7) 0.0331(11) Uani d . 1 1 . .
    C C2 0.6166(6) 0.7012(3) 0.2436(7) 0.0374(12) Uani d . 1 1 . .
    C C12 0.4886(6) 0.4387(3) 0.1880(7) 0.0360(11) Uani d . 1 1 . .
    H H12 0.5106 0.4160 0.0759 0.043 Uiso calc R 1 1 . .
    C C5 0.9429(7) 0.7315(3) 0.2022(8) 0.0441(13) Uani d . 1 1 . .
    H H5 1.0511 0.7413 0.1871 0.053 Uiso calc R 1 1 . .
    C C3 0.6696(7) 0.7671(3) 0.2287(8) 0.0434(13) Uani d . 1 1 . .
    H H3 0.5954 0.8019 0.2342 0.052 Uiso calc R 1 1 . .
    C C4 0.8297(8) 0.7822(3) 0.2060(8) 0.0461(14) Uani d . 1 1 . .
    H H4 0.8617 0.8267 0.1933 0.055 Uiso calc R 1 1 . .
    C C1 0.4405(7) 0.6864(4) 0.2685(11) 0.0618(18) Uani d . 1 1 . .
    H H1D 0.4111 0.6935 0.3982 0.093 Uiso calc R 1 1 . .
    H H1E 0.4196 0.6404 0.2346 0.093 Uiso calc R 1 1 . .
    H H1F 0.3787 0.7156 0.1886 0.093 Uiso calc R 1 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 . 1.444(4) ?
    S1 O2 . 1.446(4) ?
    S1 O3 . 1.446(4) ?
    S1 C8 . 1.795(5) ?
    N1 C6 . 1.467(6) ?
    N1 H1A . 0.8900 ?
    N1 H1B . 0.8900 ?
    N1 H1C . 0.8900 ?
    C11 C10 . 1.360(7) ?
    C11 C12 . 1.422(7) ?
    C11 H11 . 0.9300 ?
    C8 C12 3_666 1.339(7) ?
    C8 C9 . 1.440(6) ?
    C9 C10 . 1.425(6) ?
    C9 C9 3_666 1.424(9) ?
    C7 C6 . 1.374(7) ?
    C7 C2 . 1.392(7) ?
    C7 H7 . 0.9300 ?
    C10 H10 . 0.9300 ?
    C6 C5 . 1.391(7) ?
    C2 C3 . 1.387(8) ?
    C2 C1 . 1.509(8) ?
    C12 C8 3_666 1.339(7) ?
    C12 H12 . 0.9300 ?
    C5 C4 . 1.381(8) ?
    C5 H5 . 0.9300 ?
    C3 C4 . 1.379(8) ?
    C3 H3 . 0.9300 ?
    C4 H4 . 0.9300 ?
    C1 H1D . 0.9600 ?
    C1 H1E . 0.9600 ?
    C1 H1F . 0.9600 ?
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
    O1 S1 O2 . . 113.3(3) ?
    O1 S1 O3 . . 112.6(3) ?
    O2 S1 O3 . . 111.3(2) ?
    O1 S1 C8 . . 106.8(2) ?
    O2 S1 C8 . . 106.8(2) ?
    O3 S1 C8 . . 105.5(2) ?
    C6 N1 H1A . . 109.5 ?
    C6 N1 H1B . . 109.5 ?
    H1A N1 H1B . . 109.5 ?
    C6 N1 H1C . . 109.5 ?
    H1A N1 H1C . . 109.5 ?
    H1B N1 H1C . . 109.5 ?
    C10 C11 C12 . . 120.2(5) ?
    C10 C11 H11 . . 119.9 ?
    C12 C11 H11 . . 119.9 ?
    C12 C8 C9 3_666 . 121.3(4) ?
    C12 C8 S1 3_666 . 118.5(4) ?
    C9 C8 S1 . . 120.1(3) ?
    C10 C9 C9 . 3_666 119.2(5) ?
    C10 C9 C8 . . 123.0(4) ?
    C9 C9 C8 3_666 . 117.8(5) ?
    C6 C7 C2 . . 120.5(5) ?
    C6 C7 H7 . . 119.8 ?
    C2 C7 H7 . . 119.8 ?
    C11 C10 C9 . . 120.7(4) ?
    C11 C10 H10 . . 119.7 ?
    C9 C10 H10 . . 119.7 ?
    C7 C6 C5 . . 121.4(5) ?
    C7 C6 N1 . . 120.2(5) ?
    C5 C6 N1 . . 118.5(5) ?
    C3 C2 C7 . . 117.9(5) ?
    C3 C2 C1 . . 120.3(5) ?
    C7 C2 C1 . . 121.7(5) ?
    C8 C12 C11 3_666 . 120.7(5) ?
    C8 C12 H12 3_666 . 119.6 ?
    C11 C12 H12 . . 119.6 ?
    C4 C5 C6 . . 118.3(5) ?
    C4 C5 H5 . . 120.9 ?
    C6 C5 H5 . . 120.9 ?
    C4 C3 C2 . . 121.6(5) ?
    C4 C3 H3 . . 119.2 ?
    C2 C3 H3 . . 119.2 ?
    C3 C4 C5 . . 120.4(5) ?
    C3 C4 H4 . . 119.8 ?
    C5 C4 H4 . . 119.8 ?
    C2 C1 H1D . . 109.5 ?
    C2 C1 H1E . . 109.5 ?
    H1D C1 H1E . . 109.5 ?
    C2 C1 H1F . . 109.5 ?
    H1D C1 H1F . . 109.5 ?
    H1E C1 H1F . . 109.5 ?
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
    N1 H1A O3 1_655 0.89 1.90 2.779(6) 168.3
    N1 H1B O2 1_654 0.89 1.89 2.779(6) 177.2
    N1 H1C O1 3_666 0.89 1.93 2.797(6) 165.3
data_global
_journal_date_recd_electronic     2012-05-06
_journal_date_accepted     2012-05-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      6
_journal_page_first     o1745
_journal_page_last     o1745
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812021290
_journal_coeditor_code     XU5533
_publ_contact_author_name     'Ming-Liang Liu'
_publ_contact_author_address
;
Ordered Matter Science Research Center, Southeast University,
Nanjing 211189, People's Republic of China
;
_publ_contact_author_email     'jgsdxlml@163.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Bis(3-methylanilinium) naphthalene-1,5-disulfonate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Liu, Ming-Liang' .
;
Ordered Matter Science Research Center, Southeast University,
Nanjing 211189, People's Republic of China
;
    'Chen, Zi-Qi' .
;
Ordered Matter Science Research Center, Southeast University,
Nanjing 211189, People's Republic of China
;
