##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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 data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2016-11-03
_journal_date_accepted     2016-11-07
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue     11
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616017788
_journal_coeditor_code     SU4094
_publ_contact_author_name     'Alan Kennedy'
_publ_contact_author_address
;
WestChem, Department of Pure & Applied Chemistry,
University of Strathclyde,
295 Cathedral Street,
Glasgow G1 1XL
Scotland
;
_publ_contact_author_email     'a.r.kennedy@strath.ac.uk'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '0141 548 2016'
_publ_section_title
;
4-Ammonio-5-methoxy-2-methylbenzenesulfonate
;
loop_
    _publ_author_name
    _publ_author_address
    'Kennedy, Alan R.'
;
WestChem, Department of Pure & Applied Chemistry,
University of Strathclyde,
295 Cathedral Street,
Glasgow G1 1XL
Scotland
;
    'Silva de Moraes, Lygia'
;
WestChem, Department of Pure & Applied Chemistry,
University of Strathclyde,
295 Cathedral Street,
Glasgow G1 1XL
Scotland
;
_publ_section_synopsis
;
The title compound crystallizes as a zwitterion, with the negatively charged
benzenesulfonate group and the positively charged NH₃⁺ group in mutually
para positions. All the non-H atoms, except for one O atom of the
sulfonate group, lie on a crystallographic mirror plane (Z' = 1/2). In
the crystal, molecules are linked by N---H...O hydrogen bonds, forming layers
parallel to the bc plane.
;
_chemical_name_systematic     '4-Azaniumyl-5-methoxy-2-methylbenzenesulfonate'
_chemical_name_common     ?
_chemical_formula_moiety     'H4 N +, C8 H7 O4 S -'
_chemical_formula_sum     'C8 H11 N O4 S'
_chemical_formula_iupac     'N H4 +, C8 H7 O4 S -'
_chemical_formula_weight     217.24
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/m'
_space_group_name_Hall     '-P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
    '-x, -y, -z'
    'x, -y-1/2, z'
_cell_length_a     8.0644(3)
_cell_length_b     6.9410(2)
_cell_length_c     8.6192(3)
_cell_angle_alpha     90
_cell_angle_beta     105.039(4)
_cell_angle_gamma     90
_cell_volume     465.94(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3052
_cell_measurement_theta_min     3.82
_cell_measurement_theta_max     28.38
_cell_measurement_temperature     123(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.34
_exptl_crystal_size_mid     0.19
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.548
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     228
_exptl_absorpt_coefficient_mu     0.335
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.95959
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     123(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4897
_diffrn_reflns_av_R_equivalents     0.0170
_diffrn_reflns_theta_min     3.084
_diffrn_reflns_theta_max     28.897
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.901
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     1187
_reflns_number_gt     1101
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0315
_refine_ls_R_factor_gt     0.0289
_refine_ls_wR_factor_gt     0.0792
_refine_ls_wR_factor_ref     0.0813
_refine_ls_goodness_of_fit_ref     1.098
_refine_ls_restrained_S_all     1.098
_refine_ls_number_reflns     1187
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0421P)²+0.2128P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_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     0.338
_refine_diff_density_min     -0.456
_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
;
Crysalis PRO (Agilent, 2014)
;
_computing_cell_refinement
;
Crysalis PRO (Agilent, 2014)
;
_computing_data_reduction
;
Crysalis PRO (Agilent, 2014)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.3390(2) 0.2500 0.5975(2) 0.0141(3) Uani d 1 . .
    C C2 0.2229(2) 0.2500 0.4465(2) 0.0153(4) Uani d 1 . .
    H H2 0.1029 0.2500 0.4370 0.018 Uiso calc 1 . .
    C C3 0.2838(2) 0.2500 0.3100(2) 0.0145(3) Uani d 1 . .
    C C4 0.4604(2) 0.2500 0.3286(2) 0.0136(3) Uani d 1 . .
    C C5 0.5753(2) 0.2500 0.4784(2) 0.0143(3) Uani d 1 . .
    H H5 0.6951 0.2500 0.4868 0.017 Uiso calc 1 . .
    C C6 0.5174(2) 0.2500 0.6183(2) 0.0139(3) Uani d 1 . .
    C C8 0.6490(2) 0.2500 0.7788(2) 0.0179(4) Uani d 1 . .
    N N1 0.5211(2) 0.2500 0.18268(18) 0.0160(3) Uani d 1 . .
    O O1 0.18687(16) 0.2500 0.15613(15) 0.0203(3) Uani d 1 . .
    O O2 0.06437(18) 0.2500 0.70299(17) 0.0283(4) Uani d 1 . .
    O O3 0.31405(13) 0.07835(14) 0.85950(11) 0.0242(3) Uani d 1 . .
    S S1 0.24756(5) 0.2500 0.76544(5) 0.01480(15) Uani d 1 . .
    C C7 0.0052(3) 0.2500 0.1290(3) 0.0410(7) Uani d 1 . .
    H H1N 0.583(2) 0.146(2) 0.1771(19) 0.023(4) Uiso d 1 . .
    H H2N 0.430(4) 0.2500 0.097(3) 0.037(7) Uiso d 1 . .
    H H8B 0.642(2) 0.140(3) 0.844(2) 0.033(5) Uiso d 1 . .
    H H7B -0.033(3) 0.136(3) 0.178(3) 0.053(6) Uiso d 1 . .
    H H7A -0.036(4) 0.2500 0.022(4) 0.056(9) Uiso d 1 . .
    H H8A 0.762(4) 0.2500 0.763(3) 0.043(8) Uiso d 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
    C1 C2 . 1.392(2) ?
    C1 C6 . 1.403(2) ?
    C1 S1 . 1.7869(17) ?
    C2 C3 . 1.388(2) ?
    C2 H2 . 0.9500 ?
    C3 O1 . 1.354(2) ?
    C3 C4 . 1.391(2) ?
    C4 C5 . 1.380(2) ?
    C4 N1 . 1.464(2) ?
    C5 C6 . 1.401(2) ?
    C5 H5 . 0.9500 ?
    C6 C8 . 1.510(2) ?
    C8 H8B . 0.960(18) ?
    C8 H8A . 0.96(3) ?
    N1 H1N . 0.886(18) ?
    N1 H2N . 0.89(3) ?
    O1 C7 . 1.422(3) ?
    O2 S1 . 1.4351(14) ?
    O3 S1 . 1.4625(10) ?
    S1 O3 4_565 1.4624(10) ?
    C7 H7B . 0.99(2) ?
    C7 H7A . 0.90(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
    _geom_angle_publ_flag
    C2 C1 C6 . . 122.56(15) ?
    C2 C1 S1 . . 116.02(13) ?
    C6 C1 S1 . . 121.42(13) ?
    C3 C2 C1 . . 119.50(16) ?
    C3 C2 H2 . . 120.2 ?
    C1 C2 H2 . . 120.2 ?
    O1 C3 C2 . . 126.10(16) ?
    O1 C3 C4 . . 115.26(15) ?
    C2 C3 C4 . . 118.64(16) ?
    C5 C4 C3 . . 121.77(15) ?
    C5 C4 N1 . . 120.73(15) ?
    C3 C4 N1 . . 117.49(15) ?
    C4 C5 C6 . . 120.80(16) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 H5 . . 119.6 ?
    C5 C6 C1 . . 116.72(15) ?
    C5 C6 C8 . . 118.44(15) ?
    C1 C6 C8 . . 124.83(15) ?
    C6 C8 H8B . . 113.8(11) ?
    C6 C8 H8A . . 109.9(17) ?
    H8B C8 H8A . . 106.4(14) ?
    C4 N1 H1N . . 111.3(11) ?
    C4 N1 H2N . . 108.6(18) ?
    H1N N1 H2N . . 108.0(14) ?
    C3 O1 C7 . . 118.00(15) ?
    O2 S1 O3 . 4_565 113.68(5) ?
    O2 S1 O3 . . 113.68(5) ?
    O3 S1 O3 4_565 . 109.11(8) ?
    O2 S1 C1 . . 107.28(8) ?
    O3 S1 C1 4_565 . 106.27(5) ?
    O3 S1 C1 . . 106.27(5) ?
    O1 C7 H7B . . 110.8(13) ?
    O1 C7 H7A . . 105(2) ?
    H7B C7 H7A . . 111.6(17) ?
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
    C6 C1 C2 C3 . . . . 0.0000(10)
                                 ?
    S1 C1 C2 C3 . . . . 180.000000 ?
    C1 C2 C3 O1 . . . . 180.000000 ?
    C1 C2 C3 C4 . . . . 0.000000 ?
    O1 C3 C4 C5 . . . . 180.000000 ?
    C2 C3 C4 C5 . . . . 0.000000 ?
    O1 C3 C4 N1 . . . . 0.000000 ?
    C2 C3 C4 N1 . . . . 180.000000 ?
    C3 C4 C5 C6 . . . . 0.000000 ?
    N1 C4 C5 C6 . . . . 180.000000 ?
    C4 C5 C6 C1 . . . . 0.0000(10)
                                 ?
    C4 C5 C6 C8 . . . . 180.000000 ?
    C2 C1 C6 C5 . . . . 0.0000(10)
                                 ?
    S1 C1 C6 C5 . . . . 180.000000 ?
    C2 C1 C6 C8 . . . . 180.0000(10)
                                   ?
    S1 C1 C6 C8 . . . . 0.0000(10)
                                 ?
    C2 C3 O1 C7 . . . . 0.000000 ?
    C4 C3 O1 C7 . . . . 180.000000 ?
    C2 C1 S1 O2 . . . . 0.000000 ?
    C6 C1 S1 O2 . . . . 180.000000 ?
    C2 C1 S1 O3 . . . 4_565 -121.93(5) ?
    C6 C1 S1 O3 . . . 4_565 58.07(5) ?
    C2 C1 S1 O3 . . . . 121.93(5) ?
    C6 C1 S1 O3 . . . . -58.07(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 H1N O3 3_656 0.89(2) 1.83(2) 2.7100(13) 171.9(16)
    N1 H2N O3 1_554 0.89(3) 2.35(3) 3.0909(18) 140.7(14)
    N1 H2N O3 4_564 0.89(3) 2.35(3) 3.0909(18) 140.7(14)
