#------------------------------------------------------------------------------
#$Date: 2016-11-09 04:25:35 +0200 (Wed, 09 Nov 2016) $
#$Revision: 188338 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/45/1544525.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_1544525
loop_
_publ_author_name
'Kennedy, Alan R.'
'Silva de Moraes, Lygia'
_publ_section_title
;
 4-Ammonio-5-methoxy-2-methylbenzenesulfonate
;
_journal_coeditor_code           SU4094
_journal_issue                   11
_journal_name_full               IUCrData
_journal_page_first              x161778
_journal_paper_doi               10.1107/S2414314616017788
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'N H4 +, C8 H7 O4 S -'
_chemical_formula_moiety         'H4 N +, C8 H7 O4 S -'
_chemical_formula_sum            'C8 H11 N O4 S'
_chemical_formula_weight         217.24
_chemical_name_systematic        4-Azaniumyl-5-methoxy-2-methylbenzenesulfonate
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.039(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0644(3)
_cell_length_b                   6.9410(2)
_cell_length_c                   8.6192(3)
_cell_measurement_reflns_used    3052
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.38
_cell_measurement_theta_min      3.82
_cell_volume                     465.94(3)
_computing_cell_refinement
;
Crysalis PRO (Agilent, 2014)
;
_computing_data_collection
;
Crysalis PRO (Agilent, 2014)
;
_computing_data_reduction
;
Crysalis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.897
_diffrn_reflns_theta_min         3.084
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       plate
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.456
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0421P)²+0.2128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                1101
_reflns_number_total             1187
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su4094sup1.cif
_cod_data_source_block           I
_cod_database_code               1544525
_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.
;
loop_
_space_group_symop_operation_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_occupancy
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
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 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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
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_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)
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_4
_geom_torsion
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)

_cod_database_fobs_code 1544525
