#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/48/2234861.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_2234861
loop_
_publ_author_name
'Gao, Shan'
'Ng, Seik Weng'
_publ_section_title
;
 Benzene-1,2-di(aminium) naphthalene-1,5-disulfonate methanol monosolvate
 trihydrate
;
_journal_coeditor_code           XU5520
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1574
_journal_paper_doi               10.1107/S1600536812018284
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac
'C6 H10 N2 2+, C10 H6 O6 S2 2-, C H4 O, 3H2 O'
_chemical_formula_moiety
'C6 H10 N2 2+, C10 H6 O6 S2 2-, C H4 O, 3(H2 O)'
_chemical_formula_sum            'C17 H26 N2 O10 S2'
_chemical_formula_weight         482.52
_chemical_name_systematic
;
Benzene-1,2-di(aminium) naphthalene-1,5-disulfonate methanol monosolvate
trihydrate
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.390(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1727(15)
_cell_length_b                   13.681(2)
_cell_length_c                   9.5173(15)
_cell_measurement_reflns_used    6427
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.07
_cell_volume                     1052.7(3)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       'ω scan'
_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  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10378
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_T_max  0.9432
_exptl_absorpt_correction_T_min  0.9262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.852
_refine_diff_density_min         -0.409
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0909P)²+0.6772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1573
_refine_ls_wR_factor_ref         0.1762
_reflns_number_gt                1935
_reflns_number_total             2503
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5520.cif
_cod_data_source_block           I
_cod_original_cell_volume        1052.8(3)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2234861
_cod_database_fobs_code          2234861
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.71163(7) 0.51770(5) 0.72850(6) 0.0322(2) Uani d . 1 1 . .
O O1 0.6469(2) 0.61258(14) 0.6776(2) 0.0425(5) Uani d . 1 1 . .
O O2 0.6097(2) 0.43755(15) 0.6701(2) 0.0443(5) Uani d . 1 1 . .
O O3 0.7450(3) 0.51585(15) 0.8836(2) 0.0433(5) Uani d . 1 1 . .
O O1w 0.5509(5) 0.7500 1.2108(4) 0.0707(10) Uani d S 1 2 . .
H H1w 0.4934 0.6998 1.1902 0.106 Uiso d R 1 1 . .
N N1 0.4198(5) 0.7500 0.7729(4) 0.0509(9) Uani d S 1 2 . .
H H11 0.3788 0.7500 0.8535 0.076 Uiso calc SR 1 2 . .
H H12 0.4809 0.8025 0.7685 0.076 Uiso calc R 1 1 . .
N N2 0.4862(4) 0.7500 0.4847(3) 0.0368(7) Uani d S 1 2 . .
H H21 0.4867 0.7500 0.3923 0.055 Uiso calc SR 1 2 . .
H H22 0.5374 0.6975 0.5221 0.055 Uiso calc R 1 1 . .
C C1 0.9077(3) 0.50513(18) 0.6689(3) 0.0300(5) Uani d . 1 1 . .
C C2 0.9198(3) 0.50489(17) 0.5204(3) 0.0292(5) Uani d . 1 1 . .
C C3 0.7803(3) 0.51357(19) 0.4131(3) 0.0338(6) Uani d . 1 1 . .
H H3 0.6752 0.5191 0.4388 0.041 Uiso calc R 1 1 . .
C C4 0.7984(3) 0.5140(2) 0.2731(3) 0.0387(6) Uani d . 1 1 . .
H H4A 0.7057 0.5207 0.2045 0.046 Uiso calc R 1 1 . .
C C5 0.9552(3) 0.5044(2) 0.2309(3) 0.0373(6) Uani d . 1 1 . .
H H5 0.9659 0.5044 0.1349 0.045 Uiso calc R 1 1 . .
C C6 0.2850(5) 0.7500 0.6545(4) 0.0354(8) Uani d S 1 2 . .
C C7 0.1240(5) 0.7500 0.6818(5) 0.0453(10) Uani d S 1 2 . .
H H7 0.1025 0.7500 0.7751 0.054 Uiso calc SR 1 2 . .
C C8 -0.0050(5) 0.7500 0.5712(6) 0.0527(11) Uani d S 1 2 . .
H H8 -0.1133 0.7500 0.5904 0.063 Uiso calc SR 1 2 . .
C C9 0.0245(6) 0.7500 0.4325(5) 0.0499(10) Uani d S 1 2 . .
H H9 -0.0631 0.7500 0.3582 0.060 Uiso calc SR 1 2 . .
C C10 0.1866(5) 0.7500 0.4045(4) 0.0431(9) Uani d S 1 2 . .
H H10 0.2077 0.7500 0.3111 0.052 Uiso calc SR 1 2 . .
C C11 0.3153(4) 0.7500 0.5139(4) 0.0315(7) Uani d S 1 2 . .
O O4 0.7361(8) 0.6961(4) 1.0177(6) 0.0782(17) Uani d P 0.50 1 A -1
H H4 0.7426 0.6406 0.9812 0.117 Uiso calc PR 0.50 1 A -1
C C12 0.8778(11) 0.751(2) 1.0006(8) 0.090(3) Uani d S 0.5 1 A -1
H H12A 0.8778 0.8110 1.0533 0.135 Uiso calc PR 0.50 1 A -1
H H12B 0.8767 0.7658 0.9018 0.135 Uiso calc PR 0.50 1 A -1
H H12C 0.9753 0.7143 1.0351 0.135 Uiso calc PR 0.50 1 A -1
O O2w 0.4770(6) 0.6054(4) 0.9855(5) 0.0635(13) Uani d P 0.50 1 B -1
H H2w1 0.3897 0.6342 0.9987 0.095 Uiso d PR 0.50 1 B -1
H H2w2 0.4637 0.5451 0.9955 0.095 Uiso d PR 0.50 1 B -1
O O2w' 0.2979(7) 0.6729(4) 1.0117(5) 0.0657(13) Uani d P 0.50 1 C -2
H H2w3 0.3789 0.6375 1.0001 0.099 Uiso d PR 0.50 1 C -2
H H2w4 0.2196 0.6366 1.0271 0.099 Uiso d PR 0.50 1 C -2
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
O2 S1 O1 . . 112.86(13)
O2 S1 O3 . . 112.92(12)
O1 S1 O3 . . 110.88(12)
O2 S1 C1 . . 107.45(12)
O1 S1 C1 . . 106.22(12)
O3 S1 C1 . . 105.98(12)
C6 N1 H11 . . 109.5
C6 N1 H12 . . 109.5
H11 N1 H12 . . 109.5
C11 N2 H21 . . 109.5
C11 N2 H22 . . 109.5
H21 N2 H22 . . 109.5
C5 C1 C2 3_766 . 121.4(2)
C5 C1 S1 3_766 . 118.00(19)
C2 C1 S1 . . 120.56(19)
C3 C2 C2 . 3_766 119.0(3)
C3 C2 C1 . . 123.1(2)
C2 C2 C1 3_766 . 117.9(3)
C4 C3 C2 . . 120.9(2)
C4 C3 H3 . . 119.6
C2 C3 H3 . . 119.6
C3 C4 C5 . . 120.9(2)
C3 C4 H4A . . 119.5
C5 C4 H4A . . 119.5
C1 C5 C4 3_766 . 119.9(2)
C1 C5 H5 3_766 . 120.1
C4 C5 H5 . . 120.1
C7 C6 C11 . . 119.2(4)
C7 C6 N1 . . 119.3(3)
C11 C6 N1 . . 121.5(3)
C8 C7 C6 . . 120.1(4)
C8 C7 H7 . . 119.9
C6 C7 H7 . . 119.9
C9 C8 C7 . . 120.8(4)
C9 C8 H8 . . 119.6
C7 C8 H8 . . 119.6
C8 C9 C10 . . 119.3(4)
C8 C9 H9 . . 120.3
C10 C9 H9 . . 120.3
C11 C10 C9 . . 120.2(4)
C11 C10 H10 . . 119.9
C9 C10 H10 . . 119.9
C10 C11 C6 . . 120.4(3)
C10 C11 N2 . . 120.3(3)
C6 C11 N2 . . 119.3(3)
H2w1 O2w H2w2 . . 108.5
H2w2 O2w H2w3 . . 108.3
H2w1 O2w' H2w4 . . 109.5
H2w3 O2w' H2w4 . . 108.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 O2 . 1.439(2)
S1 O1 . 1.4578(19)
S1 O3 . 1.461(2)
S1 C1 . 1.785(2)
O1w H1w . 0.8391
N1 C6 . 1.456(5)
N1 H11 . 0.8800
N1 H12 . 0.8800
N2 C11 . 1.463(4)
N2 H21 . 0.8800
N2 H22 . 0.8800
C1 C5 3_766 1.367(4)
C1 C2 . 1.430(3)
C2 C3 . 1.420(4)
C2 C2 3_766 1.428(5)
C3 C4 . 1.362(4)
C3 H3 . 0.9300
C4 C5 . 1.404(4)
C4 H4A . 0.9300
C5 C1 3_766 1.367(4)
C5 H5 . 0.9300
C6 C7 . 1.377(5)
C6 C11 . 1.396(5)
C7 C8 . 1.377(7)
C7 H7 . 0.9300
C8 C9 . 1.376(7)
C8 H8 . 0.9300
C9 C10 . 1.389(6)
C9 H9 . 0.9300
C10 C11 . 1.368(5)
C10 H10 . 0.9300
O4 C12 . 1.41(2)
O4 H4 . 0.8400
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
O2w H2w1 . 0.8401
O2w H2w2 . 0.8400
O2w H2w3 . 0.9423
O2w' H2w1 . 0.9412
O2w' H2w3 . 0.8400
O2w' H2w4 . 0.8400
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 H4 O3 . 0.84 1.94 2.783(6) 175
O1w H1w O2w . 0.84 2.32 2.915(6) 128
O1w H1w O2w' . 0.84 2.19 2.799(7) 130
O2w H2w2 O3 3_667 0.84 2.35 2.873(5) 121
O2w' H2w4 O3 3_667 0.84 2.25 2.808(6) 124
N1 H12 O1 4_575 0.88 2.07 2.880(3) 153
N1 H11 O2w' . 0.88 2.03 2.816(5) 149
N2 H22 O1 . 0.88 1.99 2.815(3) 156
N2 H21 O1w 1_554 0.88 1.88 2.735(4) 164
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_4
_geom_torsion
O2 S1 C1 C5 . 3_766 -120.4(2)
O1 S1 C1 C5 . 3_766 118.6(2)
O3 S1 C1 C5 . 3_766 0.6(3)
O2 S1 C1 C2 . . 59.5(2)
O1 S1 C1 C2 . . -61.5(2)
O3 S1 C1 C2 . . -179.51(19)
C5 C1 C2 C3 3_766 . 179.3(3)
S1 C1 C2 C3 . . -0.5(3)
C5 C1 C2 C2 3_766 3_766 -0.5(4)
S1 C1 C2 C2 . 3_766 179.7(2)
C2 C2 C3 C4 3_766 . -0.9(4)
C1 C2 C3 C4 . . 179.3(2)
C2 C3 C4 C5 . . 0.9(4)
C3 C4 C5 C1 . 3_766 -0.3(4)
C11 C6 C7 C8 . . 0.000(2)
N1 C6 C7 C8 . . 180.0000(10)
C6 C7 C8 C9 . . 0.000(2)
C7 C8 C9 C10 . . 0.000(2)
C8 C9 C10 C11 . . 0.0000(10)
C9 C10 C11 C6 . . 0.0
C9 C10 C11 N2 . . 180.0
C7 C6 C11 C10 . . 0.0000(10)
N1 C6 C11 C10 . . 180.0000(10)
C7 C6 C11 N2 . . 180.0000(10)
N1 C6 C11 N2 . . 0.0000(10)
