#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/19/2231955.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_2231955
loop_
_publ_author_name
'Wei, Bin'
_publ_section_title
;
 Dimethyl(4-methylphenyl)ammonium naphthalene-1,5-disulfonate dihydrate
;
_journal_coeditor_code           JH2329
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2678
_journal_paper_doi               10.1107/S1600536811037068
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '2C9 H14 N +, C10 H6 O6 S2 2-, 2H2 O'
_chemical_formula_moiety         '2(C9 H14 N +), C10 H6 O6 S2 2-, 2(H2 O)'
_chemical_formula_sum            'C28 H38 N2 O8 S2'
_chemical_formula_weight         594.74
_chemical_name_systematic
;
Dimethyl(4-methylphenyl)ammonium 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                109.59(3)
_cell_angle_beta                 115.79(3)
_cell_angle_gamma                98.39(3)
_cell_formula_units_Z            1
_cell_length_a                   9.2660(19)
_cell_length_b                   9.882(2)
_cell_length_c                   10.260(2)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.480
_cell_measurement_theta_min      3.005
_cell_volume                     748.3(5)
_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  '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 SCXmini'
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7762
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             314
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.340
_refine_ls_extinction_coef       0.030(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0587P)²+0.1813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                2951
_reflns_number_total             3421
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jh2329.cif
_cod_data_source_block           I
_cod_original_cell_volume        748.3(3)
_cod_database_code               2231955
_cod_database_fobs_code          2231955
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
C C1 0.5316(3) 0.4244(2) 0.3073(3) 0.0732(7) Uani d . 1 1
H H1A 0.5825 0.4690 0.2607 0.110 Uiso calc R 1 1
H H1B 0.6194 0.4366 0.4096 0.110 Uiso calc R 1 1
H H1C 0.4552 0.4746 0.3232 0.110 Uiso calc R 1 1
N N1 0.14101(18) -0.21478(16) -0.12073(17) 0.0374(3) Uani d . 1 1
O O1 0.29693(16) -0.24956(14) 0.32982(15) 0.0444(3) Uani d . 1 1
S S1 0.13241(5) -0.27559(4) 0.31891(4) 0.03323(14) Uani d . 1 1
C C2 0.4338(2) 0.2567(2) 0.1950(2) 0.0487(4) Uani d . 1 1
O O2 0.10384(18) -0.37468(13) 0.38791(16) 0.0482(3) Uani d . 1 1
C C3 0.3514(3) 0.2034(2) 0.0300(3) 0.0649(6) Uani d . 1 1
H H3 0.3587 0.2722 -0.0123 0.078 Uiso d R 1 1
O O3 -0.00765(16) -0.32258(14) 0.15568(14) 0.0466(3) Uani d . 1 1
C C4 0.2579(3) 0.0502(2) -0.0752(2) 0.0590(6) Uani d . 1 1
H H4 0.2035 0.0167 -0.1865 0.071 Uiso d R 1 1
O O4 0.26401(18) 0.60704(17) 0.02223(18) 0.0468(3) Uani d . 1 1
C C5 0.2464(2) -0.05151(19) -0.0131(2) 0.0369(4) Uani d . 1 1
C C6 0.3283(2) -0.0021(2) 0.1516(2) 0.0442(4) Uani d . 1 1
H H6 0.3209 -0.0714 0.1933 0.053 Uiso d R 1 1
C C7 0.4220(3) 0.1516(2) 0.2548(2) 0.0495(5) Uani d . 1 1
H H7 0.4779 0.1848 0.3661 0.059 Uiso d R 1 1
C C9 0.1372(3) -0.2773(2) -0.2766(2) 0.0580(5) Uani d . 1 1
H H9A 0.0704 -0.2369 -0.3454 0.087 Uiso calc R 1 1
H H9B 0.0872 -0.3868 -0.3291 0.087 Uiso calc R 1 1
H H9C 0.2515 -0.2485 -0.2556 0.087 Uiso calc R 1 1
C C10 -0.0362(3) -0.2446(2) -0.1518(3) 0.0573(5) Uani d . 1 1
H H10A -0.0325 -0.2135 -0.0508 0.086 Uiso calc R 1 1
H H10B -0.1006 -0.3519 -0.2186 0.086 Uiso calc R 1 1
H H10C -0.0897 -0.1877 -0.2060 0.086 Uiso calc R 1 1
C C11 0.2843(2) 0.02932(18) 0.5176(2) 0.0371(4) Uani d . 1 1
H H11 0.3775 0.0157 0.5088 0.045 Uiso d R 1 1
C C15 -0.00608(18) -0.07490(15) 0.45203(17) 0.0275(3) Uani d . 1 1
C C16 0.13837(19) -0.09301(16) 0.43905(17) 0.0294(3) Uani d . 1 1
C C17 -0.1605(2) -0.19878(17) 0.37400(19) 0.0350(3) Uani d . 1 1
H H17 -0.1695 -0.2968 0.3124 0.042 Uiso d R 1 1
C C18 -0.2949(2) -0.17579(18) 0.3883(2) 0.0412(4) Uani d . 1 1
H H18 -0.3954 -0.2581 0.3351 0.049 Uiso d R 1 1
H H10 0.186(3) -0.267(2) -0.068(2) 0.043(5) Uiso d . 1 1
H H4A 0.268(3) 0.640(3) 0.111(4) 0.073(8) Uiso d . 1 1
H H4B 0.187(3) 0.519(3) -0.036(3) 0.075(8) Uiso 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
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
C5 N1 C9 . . 114.42(14)
C5 N1 C10 . . 111.22(14)
C9 N1 C10 . . 110.28(16)
C5 N1 H10 . . 107.1(13)
C9 N1 H10 . . 107.0(13)
C10 N1 H10 . . 106.4(13)
O2 S1 O3 . . 113.10(9)
O2 S1 O1 . . 113.24(8)
O3 S1 O1 . . 112.12(8)
O2 S1 C16 . . 106.42(7)
O3 S1 C16 . . 105.32(8)
O1 S1 C16 . . 105.85(8)
C3 C2 C7 . . 117.88(17)
C3 C2 C1 . . 121.06(19)
C7 C2 C1 . . 121.1(2)
C2 C3 C4 . . 121.90(18)
C2 C3 H3 . . 119.0
C4 C3 H3 . . 119.1
C5 C4 C3 . . 119.14(18)
C5 C4 H4 . . 120.4
C3 C4 H4 . . 120.4
H4A O4 H4B . . 105(2)
C4 C5 C6 . . 120.44(17)
C4 C5 N1 . . 121.04(15)
C6 C5 N1 . . 118.48(15)
C5 C6 C7 . . 119.50(16)
C5 C6 H6 . . 120.3
C7 C6 H6 . . 120.3
C6 C7 C2 . . 121.13(17)
C6 C7 H7 . . 119.4
C2 C7 H7 . . 119.4
N1 C9 H9A . . 109.5
N1 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
N1 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
N1 C10 H10A . . 109.5
N1 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
N1 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
C16 C11 C18 . 2_556 120.47(15)
C16 C11 H11 . . 119.8
C18 C11 H11 2_556 . 119.8
C17 C15 C16 . . 122.94(13)
C17 C15 C15 . 2_556 118.74(17)
C16 C15 C15 . 2_556 118.32(16)
C11 C16 C15 . . 120.69(14)
C11 C16 S1 . . 118.17(12)
C15 C16 S1 . . 121.14(11)
C18 C17 C15 . . 120.86(15)
C18 C17 H17 . . 119.6
C15 C17 H17 . . 119.6
C17 C18 C11 . 2_556 120.91(15)
C17 C18 H18 . . 119.5
C11 C18 H18 2_556 . 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.506(3)
C1 H1A . 0.9600
C1 H1B . 0.9600
C1 H1C . 0.9600
N1 C5 . 1.478(2)
N1 C9 . 1.490(2)
N1 C10 . 1.492(2)
N1 H10 . 0.89(2)
O1 S1 . 1.4562(13)
S1 O2 . 1.4430(13)
S1 O3 . 1.4548(15)
S1 C16 . 1.7883(16)
C2 C3 . 1.374(3)
C2 C7 . 1.386(3)
C3 C4 . 1.384(3)
C3 H3 . 0.9299
C4 C5 . 1.373(2)
C4 H4 . 0.9300
O4 H4A . 0.84(3)
O4 H4B . 0.85(3)
C5 C6 . 1.376(2)
C6 C7 . 1.385(3)
C6 H6 . 0.9300
C7 H7 . 0.9300
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
C10 H10A . 0.9600
C10 H10B . 0.9600
C10 H10C . 0.9600
C11 C16 . 1.364(2)
C11 C18 2_556 1.406(2)
C11 H11 . 0.9300
C15 C17 . 1.422(2)
C15 C16 . 1.432(2)
C15 C15 2_556 1.432(3)
C17 C18 . 1.358(2)
C17 H17 . 0.9300
C18 C11 2_556 1.406(2)
C18 H18 . 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 H4B O3 2 0.85(3) 1.93(3) 2.778(3) 176(3)
O4 H4B S1 2 0.85(3) 2.96(3) 3.753(3) 157(2)
N1 H10 O4 1_545 0.89(2) 1.84(2) 2.723(2) 174.2(19)
O4 H4A O1 1_565 0.84(3) 2.01(3) 2.846(2) 171(2)
O4 H4A S1 1_565 0.84(3) 2.87(3) 3.6569(18) 156(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139082084
