##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'SHELXL-97'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2005-10-31
_journal_date_accepted     2005-11-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue     12
_journal_page_first     o4175
_journal_page_last     o4176
_journal_paper_category     EO
_journal_coeditor_code     AT6050
_publ_contact_author_name     'Prof. Shan Gao'
_publ_contact_author_address
;
Labortatory of Functional Materials
School of Chemistry and Materials Science
Heilongjiang University
Harbin 150080
People's Republic of China
;
_publ_contact_author_email     shangao67@yahoo.com
_publ_contact_author_fax     '(86)451 8660 8040'
_publ_contact_author_phone     '(86)451 8660 9148'
_publ_section_title
;
Dihydroxonium 1,5-naphthalenedisulfonate N,N-dimethylformamide
disolvate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Deng, Zhao-Peng' .
;
Laboratory of Functional Materials
School of Chemistry and Materials Science
Heilongjiang University
Harbin, 150080
People's Republic of China
;
    'Gao, Shan' .
;
Laboratory of Functional Materials
School of Chemistry and Materials Science
Heilongjiang University
Harbin, 150080
People's Republic of China
;
    'Huo, Li-Hua' .
;
Laboratory of Functional Materials
School of Chemistry and Materials Science
Heilongjiang University
Harbin, 150080
People's Republic of China
;
    'Zhao, Hui' .
;
Laboratory of Functional Materials
School of Chemistry and Materials Science
Heilongjiang University
Harbin, 150080
People's Republic of China
;
data_I
_chemical_name_systematic
;
Dihydroxonium 1,5-naphthalenedisulfonate N,N-dimethylformamide disolvate
;
_chemical_formula_moiety     '2H3 O +, C10 H6 O6 S2 -, 2C3 H7 N O'
_chemical_formula_sum     'C16 H26 N2 O10 S2'
_chemical_formula_iupac     '2H3 O +, C10 H6 O6 S2 -, 2C3 H7 N O'
_chemical_formula_weight     470.51
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     9.1614(18)
_cell_length_b     12.101(2)
_cell_length_c     10.053(2)
_cell_angle_alpha     90.00
_cell_angle_beta     100.10(3)
_cell_angle_gamma     90.00
_cell_volume     1097.2(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9318
_cell_measurement_theta_min     3.25
_cell_measurement_theta_max     27.45
_cell_measurement_temperature     295(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.424
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     496
_exptl_absorpt_coefficient_mu     0.297
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_correction_T_min     0.911
_exptl_absorpt_correction_T_max     0.943
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(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 R-AXIS RAPID'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     '10.000'
_diffrn_reflns_number     10588
_diffrn_reflns_av_R_equivalents     0.0147
_diffrn_reflns_av_sigmaI/netI     0.0117
_diffrn_reflns_theta_min     3.25
_diffrn_reflns_theta_max     27.47
_diffrn_reflns_theta_full     27.47
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     2507
_reflns_number_gt     2193
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0432
_refine_ls_R_factor_gt     0.0380
_refine_ls_wR_factor_gt     0.1074
_refine_ls_wR_factor_ref     0.1107
_refine_ls_goodness_of_fit_ref     1.049
_refine_ls_restrained_S_all     1.050
_refine_ls_number_reflns     2507
_refine_ls_number_parameters     147
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0663P)²+0.3282P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.521
_refine_diff_density_min     -0.267
_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     'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement     'RAPID-AUTO'
_computing_data_reduction     'CrystalStructure (Rigaku/MSC, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     SHELXL97
loop_
    _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
    _atom_site_type_symbol
    S1 0.14585(4) 0.37380(3) 0.24652(4) 0.03585(15) Uani d . 1 . . S
    O1W 0.48829(16) 0.24214(14) 0.42229(15) 0.0632(4) Uani d D 1 . . O
    O1 0.25032(16) 0.42020(12) 0.17018(14) 0.0554(4) Uani d . 1 . . O
    O2 0.20371(15) 0.27821(10) 0.32684(14) 0.0499(3) Uani d . 1 . . O
    O3 0.00218(15) 0.34940(13) 0.16396(14) 0.0569(4) Uani d . 1 . . O
    O4 0.66802(15) 0.15210(12) 0.30644(15) 0.0531(3) Uani d . 1 . . O
    N1 0.81967(18) 0.00553(15) 0.31535(18) 0.0524(4) Uani d . 1 . . N
    C1 0.15364(19) 0.66179(14) 0.44739(18) 0.0412(4) Uani d . 1 . . C
    C2 0.17900(17) 0.57714(13) 0.35873(17) 0.0372(3) Uani d . 1 . . C
    C3 0.11041(16) 0.47705(12) 0.36244(15) 0.0303(3) Uani d . 1 . . C
    C4 0.01221(15) 0.45644(11) 0.45502(14) 0.0281(3) Uani d . 1 . . C
    C5 -0.06208(18) 0.35437(13) 0.46205(17) 0.0370(3) Uani d . 1 . . C
    C6 0.8891(3) 0.0471(3) 0.2058(3) 0.0823(8) Uani d . 1 . . C
    C7 0.8689(3) -0.1014(2) 0.3770(4) 0.0849(9) Uani d . 1 . . C
    C8 0.71438(19) 0.05935(16) 0.35600(19) 0.0449(4) Uani d . 1 . . C
    H1W1 0.541(2) 0.1976(19) 0.382(2) 0.095 Uiso d D 1 . . H
    H1W2 0.3976(13) 0.240(2) 0.381(2) 0.095 Uiso d D 1 . . H
    H1W3 0.488(3) 0.217(2) 0.5029(12) 0.095 Uiso d D 1 . . H
    H1 0.2002 0.7298 0.4440 0.049 Uiso calc R 1 . . H
    H2 0.2425 0.5891 0.2974 0.045 Uiso calc R 1 . . H
    H5 -0.0477 0.2975 0.4035 0.044 Uiso calc R 1 . . H
    H6A 0.8338 0.1092 0.1642 0.124 Uiso calc R 1 . . H
    H6B 0.8904 -0.0101 0.1398 0.124 Uiso calc R 1 . . H
    H6C 0.9889 0.0697 0.2410 0.124 Uiso calc R 1 . . H
    H7A 0.8227 -0.1140 0.4542 0.127 Uiso calc R 1 . . H
    H7B 0.9747 -0.1007 0.4046 0.127 Uiso calc R 1 . . H
    H7C 0.8416 -0.1594 0.3122 0.127 Uiso calc R 1 . . H
    H8 0.6705 0.0291 0.4244 0.054 Uiso calc R 1 . . H
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0351(2) 0.0426(2) 0.0311(2) 0.00923(15) 0.00916(15) -0.00635(14)
    O1 0.0612(8) 0.0647(9) 0.0484(8) 0.0068(7) 0.0323(7) -0.0054(6)
    O2 0.0529(7) 0.0447(7) 0.0542(8) 0.0184(6) 0.0152(6) -0.0013(6)
    O3 0.0469(7) 0.0770(10) 0.0439(7) 0.0083(6) -0.0001(6) -0.0233(7)
    O4 0.0497(7) 0.0587(8) 0.0514(8) 0.0014(6) 0.0103(6) 0.0054(6)
    O1W 0.0504(8) 0.0906(12) 0.0490(8) 0.0208(8) 0.0098(7) 0.0155(8)
    N1 0.0415(8) 0.0559(9) 0.0592(10) -0.0036(7) 0.0070(7) -0.0140(7)
    C1 0.0445(9) 0.0331(8) 0.0490(10) -0.0095(6) 0.0163(7) -0.0006(7)
    C2 0.0359(8) 0.0410(8) 0.0378(8) -0.0016(6) 0.0146(6) 0.0028(6)
    C3 0.0307(7) 0.0328(7) 0.0282(7) 0.0051(5) 0.0078(5) -0.0014(5)
    C4 0.0285(7) 0.0289(7) 0.0271(7) 0.0028(5) 0.0058(5) -0.0010(5)
    C5 0.0425(8) 0.0306(7) 0.0396(8) -0.0032(6) 0.0120(7) -0.0056(6)
    C6 0.0629(15) 0.111(2) 0.0812(18) 0.0022(14) 0.0341(13) -0.0110(16)
    C7 0.0726(16) 0.0561(14) 0.124(3) 0.0080(12) 0.0114(16) -0.0077(15)
    C8 0.0390(8) 0.0525(10) 0.0422(9) -0.0097(7) 0.0043(7) -0.0069(7)
_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 . 1.4415(14) yes
    S1 O2 . 1.4564(13) yes
    S1 O3 . 1.4579(14) yes
    S1 C3 . 1.7769(15) yes
    O4 C8 . 1.270(2) yes
    N1 C8 . 1.288(2) yes
    N1 C6 . 1.455(3) yes
    N1 C7 . 1.471(3) yes
    C1 C5 3_566 1.356(2) yes
    C1 C2 . 1.404(2) yes
    C2 C3 . 1.368(2) yes
    C3 C4 . 1.425(2) yes
    C4 C5 . 1.418(2) yes
    C4 C4 3_566 1.432(3) yes
    C5 C1 3_566 1.356(2) yes
    O1W H1W1 . 0.87(2) no
    O1W H1W2 . 0.87(2) no
    O1W H1W3 . 0.87(2) no
    C1 H1 . 0.9300 no
    C2 H2 . 0.9300 no
    C5 H5 . 0.9300 no
    C6 H6A . 0.9600 no
    C6 H6B . 0.9600 no
    C6 H6C . 0.9600 no
    C7 H7A . 0.9600 no
    C7 H7B . 0.9600 no
    C7 H7C . 0.9600 no
    C8 H8 . 0.9300 no
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 C3 . . 106.86(8) yes
    O1 S1 O2 . . 113.17(8) yes
    O1 S1 O3 . . 113.16(9) yes
    O2 S1 C3 . . 106.59(7) yes
    O2 S1 O3 . . 111.05(9) yes
    O3 S1 C3 . . 105.39(7) yes
    O4 C8 N1 . . 122.66(19) yes
    C1 C5 C4 3_566 . 121.19(14) yes
    C2 C3 C4 . . 121.22(13) yes
    C2 C3 S1 . . 117.84(11) yes
    C3 C2 C1 . . 120.06(14) yes
    C3 C4 C4 . 3_566 118.04(16) yes
    C4 C3 S1 . . 120.94(11) yes
    C5 C1 C2 3_566 . 120.79(15) yes
    C5 C4 C3 . . 123.25(13) yes
    C5 C4 C4 . 3_566 118.71(16) yes
    C6 N1 C7 . . 118.7(2) yes
    C8 N1 C6 . . 121.1(2) yes
    C8 N1 C7 . . 120.2(2) yes
    O4 C8 H8 . . 118.7 no
    N1 C6 H6A . . 109.5 no
    N1 C6 H6B . . 109.5 no
    N1 C6 H6C . . 109.5 no
    N1 C7 H7A . . 109.5 no
    N1 C7 H7B . . 109.5 no
    N1 C7 H7C . . 109.5 no
    N1 C8 H8 . . 118.7 no
    C1 C2 H2 . . 120.0 no
    C1 C5 H5 3_566 . 119.4 no
    C2 C1 H1 . . 119.6 no
    C3 C2 H2 . . 120.0 no
    C4 C5 H5 . . 119.4 no
    C5 C1 H1 3_566 . 119.6 no
    H1W1 O1W H1W2 . . 109.1(14) no
    H1W1 O1W H1W3 . . 107.8(14) no
    H1W2 O1W H1W3 . . 106.1(13) no
    H6A C6 H6B . . 109.5 no
    H6A C6 H6C . . 109.5 no
    H6B C6 H6C . . 109.5 no
    H7A C7 H7B . . 109.5 no
    H7A C7 H7C . . 109.5 no
    H7B C7 H7C . . 109.5 no
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
    S1 C3 C4 C4 . . . 3_566 -179.54(13) no
    S1 C3 C4 C5 . . . . 0.4(2) no
    O1 S1 C3 C2 . . . . 1.65(15) no
    O1 S1 C3 C4 . . . . -179.11(12) no
    O2 S1 C3 C2 . . . . 122.94(13) no
    O2 S1 C3 C4 . . . . -57.83(14) no
    O3 S1 C3 C2 . . . . -118.98(14) no
    O3 S1 C3 C4 . . . . 60.25(14) no
    C1 C2 C3 C4 . . . . 0.2(2) no
    C1 C2 C3 S1 . . . . 179.43(13) no
    C2 C3 C4 C4 . . . 3_566 -0.3(2) no
    C2 C3 C4 C5 . . . . 179.60(15) no
    C3 C4 C5 C1 . . . 3_566 179.45(15) no
    C4 C4 C5 C1 3_566 . . 3_566 -0.6(3) no
    C5 C1 C2 C3 3_566 . . . 0.4(3) no
    C6 N1 C8 O4 . . . . -2.0(3) no
    C7 N1 C8 O4 . . . . 179.8(2) no
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
    O1W H1W1 O4 . 0.87(2) 1.600(11) 2.435(2) 161(3) yes
    O1W H1W2 O2 . 0.87(2) 1.824(11) 2.652(2) 161(3) yes
    O1W H1W3 O3 4_666 0.87(2) 1.792(10) 2.653(2) 173(2) yes
