#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/84/2018401.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_2018401
loop_
_publ_author_name
'Bekö, Sándor L.'
'Bats, Jan W.'
'Schmidt, Martin U.'
_publ_section_title
;
 2-Ammonio-5-chloro-4-methylbenzenesulfonate, its 1-methyl-2-pyrrolidone
 and dimethyl sulfoxide monosolvates and a corrected structure of
 2,2'-(1,4-phenylene)di(4,5-dihydroimidazolium)
 bis(4-aminobenzenesulfonate) dihydrate
;
_journal_coeditor_code           SK3426
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o45
_journal_page_last               o50
_journal_paper_doi               10.1107/S0108270111054205
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C7 H8 Cl N O3 S , C5 H9 N O'
_chemical_formula_moiety         'C7 H8 Cl N O3 S, C5 H9 N O'
_chemical_formula_sum            'C12 H17 Cl N2 O4 S'
_chemical_formula_weight         320.79
_chemical_name_systematic
;
2-ammonio-5-chloro-4-methylbenzenesulfonate 1-methyl-2-pyrrolidone
monosolvate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.538(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1917(17)
_cell_length_b                   6.9457(11)
_cell_length_c                   11.8265(13)
_cell_measurement_reflns_used    196
_cell_measurement_temperature    165(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3
_cell_volume                     727.4(2)
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      165(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Siemens SMART 1K CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12236
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         31.90
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1600
_diffrn_standards_number         239
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.570
_refine_ls_extinction_coef       0.011(3)
_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   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.05P)²+0.4P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1005
_reflns_number_gt                2131
_reflns_number_total             2552
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3426.cif
_cod_data_source_block           Ib
_cod_original_cell_volume        727.44(19)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2018401
_cod_database_fobs_code          2018401
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
Cl Cl1 -0.24641(5) 0.2500 0.43223(4) 0.02590(13) Uani d S 1 2
S S1 0.30567(5) 0.2500 0.34505(4) 0.01966(12) Uani d S 1 2
O O1 0.20108(17) 0.2500 0.22981(12) 0.0361(4) Uani d S 1 2
O O2 0.39672(12) 0.07667(17) 0.37237(10) 0.0331(3) Uani d . 1 1
O O3 0.46344(18) 0.2500 0.85413(13) 0.0363(4) Uani d S 1 2
N N1 0.42404(18) 0.2500 0.61528(14) 0.0209(3) Uani d S 1 2
N N2 0.5996(2) 0.2500 1.04493(15) 0.0389(5) Uani d S 1 2
C C1 0.19356(19) 0.2500 0.44728(15) 0.0184(3) Uani d S 1 2
C C2 0.25958(19) 0.2500 0.56809(15) 0.0181(3) Uani d S 1 2
C C3 0.1721(2) 0.2500 0.64635(16) 0.0203(3) Uani d S 1 2
H H3A 0.2199 0.2500 0.7282 0.024 Uiso calc SR 1 2
C C4 0.0141(2) 0.2500 0.60749(16) 0.0210(3) Uani d S 1 2
C C5 -0.0503(2) 0.2500 0.48688(17) 0.0209(3) Uani d S 1 2
C C6 0.03673(19) 0.2500 0.40712(16) 0.0205(3) Uani d S 1 2
H H6A -0.0109 0.2500 0.3252 0.025 Uiso calc SR 1 2
C C7 -0.0774(2) 0.2500 0.69568(19) 0.0275(4) Uani d S 1 2
C C8 0.5852(2) 0.2500 0.92992(17) 0.0311(5) Uani d S 1 2
C C9 0.7378(3) 0.2171(5) 0.9076(2) 0.0326(7) Uiso d P 0.50 1
H H9A 0.7743 0.3358 0.8779 0.039 Uiso calc PR 0.50 1
H H9B 0.7323 0.1128 0.8495 0.039 Uiso calc PR 0.50 1
C C10 0.8414(4) 0.1605(9) 1.0266(4) 0.0681(15) Uani d P 0.50 1
H H10A 0.8632 0.0207 1.0293 0.082 Uiso calc PR 0.50 1
H H10B 0.9380 0.2319 1.0425 0.082 Uiso calc PR 0.50 1
C C11 0.7555(3) 0.2134(5) 1.1153(3) 0.0381(8) Uiso d P 0.50 1
H H11A 0.7584 0.1064 1.1712 0.046 Uiso calc PR 0.50 1
H H11B 0.7992 0.3298 1.1599 0.046 Uiso calc PR 0.50 1
C C12 0.4766(4) 0.2500 1.0993(2) 0.0428(6) Uani d S 1 2
H H1A 0.470(2) 0.152(3) 0.5967(17) 0.040(5) Uiso d . 1 1
H H1B 0.449(3) 0.2500 0.691(3) 0.034(7) Uiso d S 1 2
H H7A -0.013(4) 0.2500 0.770(3) 0.055(9) Uiso d S 1 2
H H7B -0.143(3) 0.143(4) 0.686(2) 0.072(8) Uiso d . 1 1
H H12A 0.386(4) 0.2500 1.045(4) 0.066(11) Uiso d S 1 2
H H12B 0.485(3) 0.135(4) 1.148(2) 0.061(7) 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'
Cl Cl 0.1484 0.1585 '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
O1 S1 O2 . 4_565 114.13(6)
O1 S1 O2 . . 114.13(6)
O2 S1 O2 4_565 . 111.98(10)
O1 S1 C1 . . 106.27(8)
O2 S1 C1 4_565 . 104.60(5)
O2 S1 C1 . . 104.60(5)
C2 N1 H1A . . 115.3(13)
C2 N1 H1B . . 110.6(18)
H1A N1 H1B . . 104.9(16)
C8 N2 C12 . . 125.5(2)
C8 N2 C11 . . 113.1(2)
C12 N2 C11 . . 120.6(2)
C6 C1 C2 . . 118.44(16)
C6 C1 S1 . . 120.11(13)
C2 C1 S1 . . 121.45(13)
C3 C2 C1 . . 121.03(16)
C3 C2 N1 . . 118.18(16)
C1 C2 N1 . . 120.79(15)
C2 C3 C4 . . 121.29(16)
C2 C3 H3A . . 119.4
C4 C3 H3A . . 119.4
C5 C4 C3 . . 117.14(16)
C5 C4 C7 . . 123.17(17)
C3 C4 C7 . . 119.69(17)
C4 C5 C6 . . 122.10(16)
C4 C5 Cl1 . . 119.63(14)
C6 C5 Cl1 . . 118.28(14)
C5 C6 C1 . . 120.00(16)
C5 C6 H6A . . 120.0
C1 C6 H6A . . 120.0
C4 C7 H7A . . 109(2)
C4 C7 H7B . . 112.0(16)
H7A C7 H7B . . 109.8(19)
O3 C8 N2 . . 124.4(2)
O3 C8 C9 . . 125.2(2)
N2 C8 C9 . . 109.64(19)
C8 C9 C10 . . 104.9(2)
C8 C9 H9A . . 110.8
C10 C9 H9A . . 110.8
C8 C9 H9B . . 110.8
C10 C9 H9B . . 110.8
H9A C9 H9B . . 108.8
C11 C10 C9 . . 105.3(3)
C11 C10 H10A . . 110.7
C9 C10 H10A . . 110.7
C11 C10 H10B . . 110.7
C9 C10 H10B . . 110.7
H10A C10 H10B . . 108.8
N2 C11 C10 . . 105.0(2)
N2 C11 H11A . . 110.7
C10 C11 H11A . . 110.7
N2 C11 H11B . . 110.7
C10 C11 H11B . . 110.7
H11A C11 H11B . . 108.8
N2 C12 H12A . . 111(2)
N2 C12 H12B . . 108.0(14)
H12A C12 H12B . . 109.7(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C5 . 1.7443(18)
S1 O1 . 1.4421(15)
S1 O2 4_565 1.4523(11)
S1 O2 . 1.4524(11)
S1 C1 . 1.7863(18)
O3 C8 . 1.233(3)
N1 C2 . 1.464(2)
N1 H1A . 0.86(2)
N1 H1B . 0.86(3)
N2 C8 . 1.331(3)
N2 C12 . 1.442(3)
N2 C11 . 1.474(3)
C1 C6 . 1.392(2)
C1 C2 . 1.395(2)
C2 C3 . 1.379(2)
C3 C4 . 1.400(3)
C3 H3A . 0.9500
C4 C5 . 1.390(3)
C4 C7 . 1.505(3)
C5 C6 . 1.391(3)
C6 H6A . 0.9500
C7 H7A . 0.92(4)
C7 H7B . 0.94(3)
C8 C9 . 1.512(3)
C9 C10 . 1.525(5)
C9 H9A . 0.9900
C9 H9B . 0.9900
C10 C11 . 1.518(5)
C10 H10A . 0.9900
C10 H10B . 0.9900
C11 H11A . 0.9900
C11 H11B . 0.9900
C12 H12A . 0.90(4)
C12 H12B . 0.97(3)
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
N1 H1A O2 3_656 0.86(2) 1.98(2) 2.785(2) 156(2) yes
N1 H1B O3 1_555 0.86(3) 1.90(3) 2.750(2) 169(3) yes
C3 H3A O3 1_555 0.95 2.33 3.112(3) 139 yes
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
O1 S1 C1 C6 . 0.0
O2 S1 C1 C6 4_565 121.07(5)
O2 S1 C1 C6 . -121.07(5)
O1 S1 C1 C2 . 180.0
O2 S1 C1 C2 4_565 -58.93(5)
O2 S1 C1 C2 . 58.93(5)
C6 C1 C2 C3 . 0.0
S1 C1 C2 C3 . 180.0
C6 C1 C2 N1 . 180.0
S1 C1 C2 N1 . 0.0
C1 C2 C3 C4 . 0.0
N1 C2 C3 C4 . 180.0
C2 C3 C4 C5 . 0.0
C2 C3 C4 C7 . 180.0
C3 C4 C5 C6 . 0.0
C7 C4 C5 C6 . 180.0
C3 C4 C5 Cl1 . 180.0
C7 C4 C5 Cl1 . 0.0
C4 C5 C6 C1 . 0.0
Cl1 C5 C6 C1 . 180.0
C2 C1 C6 C5 . 0.0
S1 C1 C6 C5 . 180.0
C12 N2 C8 O3 . 0.0000(10)
C11 N2 C8 O3 . 169.19(15)
C12 N2 C8 C9 . -170.75(14)
C11 N2 C8 C9 . -1.6(2)
O3 C8 C9 C10 . -160.5(3)
N2 C8 C9 C10 . 10.1(3)
C8 C9 C10 C11 . -14.2(4)
C8 N2 C11 C10 . -7.7(3)
C12 N2 C11 C10 . 162.1(3)
C9 C10 C11 N2 . 13.4(4)
