#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/76/2237608.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_2237608
loop_
_publ_author_name
'Ravikumar, B.'
'Pandiarajan, S.'
'Athimoolam, S.'
_publ_section_title
;
 Bis(4-sulfamoylanilinium) sulfate
;
_journal_coeditor_code           FB2278
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o596
_journal_paper_doi               10.1107/S1600536813007216
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '2C6 H9 N2 O2 S+, S O4 2-'
_chemical_formula_moiety         '2(C6 H9 N2 O2 S +), O4 S 2-'
_chemical_formula_sum            'C12 H18 N4 O8 S3'
_chemical_formula_weight         442.48
_chemical_name_systematic
;
Bis(4-sulfamoylanilinium) sulfate
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL/PC
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6543(6)
_cell_length_b                   9.7591(11)
_cell_length_c                   18.579(3)
_cell_measurement_reflns_used    2417
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.87
_cell_measurement_theta_min      2.39
_cell_volume                     1750.5(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
;
PLATON (Spek, 2009) and
JANA2006 (Petricek et al., 2006)
;
_computing_publication_material  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_refinement
;
SHELXTL/PC (Sheldrick, 2008) and
JANA2006 (Petricek et al., 2006)
;
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scans'
_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  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0130
_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       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18054
_diffrn_reflns_theta_full        27.75
_diffrn_reflns_theta_max         27.75
_diffrn_reflns_theta_min         2.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.476
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.511
_refine_ls_extinction_coef       0.048(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL/PC (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2054
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0478P)²+1.7836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1038
_reflns_number_gt                1950
_reflns_number_total             2054
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fb2278.cif
_cod_data_source_block           I
_cod_database_code               2237608
_cod_database_fobs_code          2237608
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, 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
C C1 0.11530(19) 0.63165(19) 0.54983(9) 0.0275(4) Uani d . 1 8
C C2 0.0350(2) 0.6931(2) 0.49691(11) 0.0346(4) Uani d . 1 8
H H2 -0.0419 0.7451 0.5098 0.041 Uiso calc R 1 8
C C3 0.0693(2) 0.6772(2) 0.42437(10) 0.0349(4) Uani d . 1 8
H H3 0.0161 0.7185 0.3887 0.042 Uiso calc R 1 8
C C4 0.18330(18) 0.59911(18) 0.40639(9) 0.0278(4) Uani d . 1 8
C C5 0.2642(2) 0.5368(2) 0.45866(10) 0.0363(4) Uani d . 1 8
H H5 0.3407 0.4846 0.4455 0.044 Uiso calc R 1 8
C C6 0.2300(2) 0.5530(2) 0.53135(10) 0.0368(4) Uani d . 1 8
H H6 0.2833 0.5115 0.5669 0.044 Uiso calc R 1 8
N N1 0.1578(2) 0.7855(2) 0.66870(10) 0.0418(4) Uani d D 1 8
H H1N 0.234(2) 0.771(3) 0.6883(13) 0.050 Uiso d D 1 8
H H2N 0.118(3) 0.863(2) 0.6780(15) 0.050 Uiso d D 1 8
N N2 0.21752(18) 0.57958(18) 0.32972(8) 0.0343(4) Uani d . 1 8
H H2A 0.1882 0.6516 0.3046 0.052 Uiso calc R 1 8
H H2B 0.1762 0.5041 0.3135 0.052 Uiso calc R 1 8
H H2C 0.3088 0.5712 0.3248 0.052 Uiso calc R 1 8
S S1 0.07157(5) 0.65527(5) 0.64256(2) 0.02962(17) Uani d . 1 8
O O1 0.11508(19) 0.53240(16) 0.68009(8) 0.0447(4) Uani d . 1 8
O O2 -0.07144(14) 0.69235(18) 0.64486(8) 0.0401(4) Uani d . 1 8
S S2 0.5000 0.61321(7) 0.7500 0.0330(2) Uani d S 1 4
O O21 0.5039(2) 0.52764(18) 0.68459(10) 0.0586(5) Uani d . 1 8
O O22 0.6198(3) 0.7004(3) 0.75120(13) 0.1099(12) Uani d . 1 8
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 . . 120.56(17)
C2 C1 S1 . . 119.64(14)
C6 C1 S1 . . 119.80(14)
C1 C2 C3 . . 120.16(17)
C1 C2 H2 . . 119.9
C3 C2 H2 . . 119.9
C4 C3 C2 . . 119.00(17)
C4 C3 H3 . . 120.5
C2 C3 H3 . . 120.5
C3 C4 C5 . . 121.45(17)
C3 C4 N2 . . 118.95(16)
C5 C4 N2 . . 119.59(17)
C4 C5 C6 . . 119.60(18)
C4 C5 H5 . . 120.2
C6 C5 H5 . . 120.2
C1 C6 C5 . . 119.24(17)
C1 C6 H6 . . 120.4
C5 C6 H6 . . 120.4
S1 N1 H1N . . 117.4(19)
S1 N1 H2N . . 121.8(19)
H1N N1 H2N . . 117(3)
C4 N2 H2A . . 109.5
C4 N2 H2B . . 109.5
H2A N2 H2B . . 109.5
C4 N2 H2C . . 109.5
H2A N2 H2C . . 109.5
H2B N2 H2C . . 109.5
O2 S1 O1 . . 118.39(10)
O2 S1 N1 . . 107.08(10)
O1 S1 N1 . . 111.18(11)
O2 S1 C1 . . 106.84(9)
O1 S1 C1 . . 106.76(9)
N1 S1 C1 . . 105.83(10)
O22 S2 O22 3_656 . 107.4(3)
O22 S2 O21 3_656 3_656 109.11(16)
O22 S2 O21 . 3_656 110.07(12)
O22 S2 O21 3_656 . 110.07(12)
O22 S2 O21 . . 109.11(16)
O21 S2 O21 3_656 . 111.04(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.389(3)
C1 C6 . 1.390(3)
C1 S1 . 1.7887(18)
C2 C3 . 1.397(3)
C2 H2 . 0.9300
C3 C4 . 1.379(3)
C3 H3 . 0.9300
C4 C5 . 1.386(3)
C4 N2 . 1.475(2)
C5 C6 . 1.399(3)
C5 H5 . 0.9300
C6 H6 . 0.9300
N1 S1 . 1.5950(19)
N1 H1N . 0.834(17)
N1 H2N . 0.866(17)
N2 H2A . 0.8900
N2 H2B . 0.8900
N2 H2C . 0.8900
S1 O2 . 1.4279(15)
S1 O1 . 1.4494(15)
S2 O22 3_656 1.4362(19)
S2 O22 . 1.436(2)
S2 O21 3_656 1.4750(18)
S2 O21 . 1.4751(18)
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 O22 3_656 0.84(2) 1.93(2) 2.743(3) 164(3)
N1 H2N O21 8_665 0.86(2) 1.99(2) 2.849(3) 168(3)
N2 H2B O2 5_566 0.89 2.30 3.043(3) 141
N2 H2B O1 7_565 0.89 2.57 3.146(2) 123
N2 H2A O22 4_466 0.89 1.90 2.787(3) 177
N2 H2C O21 5_666 0.89 2.06 2.900(3) 158
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
C6 C1 C2 C3 -0.4(3)
S1 C1 C2 C3 179.02(16)
C1 C2 C3 C4 0.3(3)
C2 C3 C4 C5 -0.2(3)
C2 C3 C4 N2 178.55(18)
C3 C4 C5 C6 0.1(3)
N2 C4 C5 C6 -178.65(18)
C2 C1 C6 C5 0.3(3)
S1 C1 C6 C5 -179.13(16)
C4 C5 C6 C1 -0.1(3)
C2 C1 S1 O2 21.96(19)
C6 C1 S1 O2 -158.59(17)
C2 C1 S1 O1 149.55(17)
C6 C1 S1 O1 -31.01(19)
C2 C1 S1 N1 -91.92(18)
C6 C1 S1 N1 87.52(18)
