#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/52/2225218.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_2225218
loop_
_publ_author_name
'Boutobba, Zina'
'Direm, Amani'
'Benali-Cherif, Nourredine'
_publ_section_title
;
 Anilinium hydrogen sulfate
;
_journal_coeditor_code           DN2534
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o595
_journal_page_last               o596
_journal_paper_doi               10.1107/S1600536810004782
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H8 N+, H S O4 -'
_chemical_formula_moiety         'C6 H8 N+, H S O4 -'
_chemical_formula_sum            'C6 H9 N O4 S'
_chemical_formula_weight         191.20
_chemical_name_common            'Bis(anilinium hydrogensulfate)'
_chemical_name_systematic        'Anilinium hydrogen sulfate'
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine-INITIALISE'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.3201(2)
_cell_length_b                   9.0891(3)
_cell_length_c                   12.8771(2)
_cell_measurement_reflns_used    16963
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.65
_cell_volume                     1676.04(7)
_computing_cell_refinement
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1998)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP32 for Windows (Farrugia,
1997) and
Platon (Spek, 2009)
;
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'ω - θ 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  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16963
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.473
_refine_ls_abs_structure_details 'Flack (1983), 2096 Friedel pairs'
_refine_ls_abs_structure_Flack   0.08(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4641
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0405
_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)+(0.0622P)²+0.1354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1172
_reflns_number_gt                3108
_reflns_number_total             4641
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2534.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2225218
_cod_database_fobs_code          2225218
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -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_disorder_assembly
_atom_site_disorder_group
N N1A 0.21732(15) 0.3085(2) 0.3390(2) 0.0432(5) Uani d . 1 . .
H H22 0.2392 0.3525 0.2823 0.065 Uiso calc R 1 . .
H H33 0.2550 0.3273 0.3924 0.065 Uiso calc R 1 . .
H H11 0.1603 0.3422 0.3530 0.065 Uiso calc R 1 . .
C C1A 0.21307(19) 0.1496(3) 0.3217(3) 0.0363(7) Uani d . 1 . .
C C2A 0.1721(3) 0.0988(4) 0.2311(3) 0.0531(8) Uani d . 1 . .
H H2A 0.1482 0.1641 0.1823 0.064 Uiso calc R 1 . .
C C3A 0.1676(3) -0.0512(4) 0.2153(3) 0.0626(10) Uani d . 1 . .
H H3A 0.1398 -0.0875 0.1553 0.075 Uiso calc R 1 . .
C C4A 0.2039(2) -0.1480(4) 0.2873(4) 0.0640(11) Uani d . 1 . .
H H4A 0.2006 -0.2489 0.2760 0.077 Uiso calc R 1 . .
C C5A 0.2449(3) -0.0940(4) 0.3758(3) 0.0555(9) Uani d . 1 . .
H H5A 0.2698 -0.1588 0.4243 0.067 Uiso calc R 1 . .
C C6A 0.2493(3) 0.0551(4) 0.3931(3) 0.0458(7) Uani d . 1 . .
H H6A 0.2770 0.0912 0.4533 0.055 Uiso calc R 1 . .
N N1B 0.52868(13) 0.2975(2) 0.5035(2) 0.0403(5) Uani d . 1 . .
H H1 0.5861 0.3342 0.4989 0.061 Uiso calc R 1 . .
H H2 0.4989 0.3397 0.5564 0.061 Uiso calc R 1 . .
H H3 0.4978 0.3154 0.4448 0.061 Uiso calc R 1 . .
C C1B 0.53385(18) 0.1390(3) 0.5207(2) 0.0330(6) Uani d . 1 . .
C C2B 0.5767(2) 0.0855(4) 0.6081(3) 0.0498(8) Uani d . 1 . .
H H2B 0.6015 0.1493 0.6573 0.060 Uiso calc R 1 . .
C C3B 0.5824(3) -0.0655(4) 0.6217(4) 0.0622(10) Uani d . 1 . .
H H3B 0.6104 -0.1037 0.6810 0.075 Uiso calc R 1 . .
C C4B 0.5467(3) -0.1590(4) 0.5479(4) 0.0622(11) Uani d . 1 . .
H H4B 0.5521 -0.2602 0.5568 0.075 Uiso calc R 1 . .
C C5B 0.5030(3) -0.1046(4) 0.4610(4) 0.0599(11) Uani d . 1 . .
H H5B 0.4775 -0.1685 0.4122 0.072 Uiso calc R 1 . .
C C6B 0.4973(3) 0.0456(4) 0.4468(3) 0.0453(7) Uani d . 1 . .
H H6B 0.4688 0.0836 0.3877 0.054 Uiso calc R 1 . .
S S1A 0.47642(6) 0.50293(6) 0.27815(5) 0.0354(3) Uani d . 1 . .
O O1A 0.53917(14) 0.5609(3) 0.3548(2) 0.0588(5) Uani d . 1 . .
O O2A 0.43955(15) 0.3610(2) 0.30490(17) 0.0501(5) Uani d . 1 . .
O O3A 0.5129(3) 0.5072(3) 0.1721(3) 0.0610(11) Uani d . 1 . .
O O4A 0.39386(13) 0.6139(2) 0.27837(19) 0.0492(5) Uani d . 1 . .
H H4 0.3495 0.5784 0.2468 0.074 Uiso d R 1 . .
S S1B 0.22562(6) 0.50860(7) 0.06533(5) 0.0340(3) Uani d . 1 . .
O O1B 0.29288(13) 0.5696(2) -0.00469(18) 0.0543(5) Uani d . 1 . .
O O2B 0.18378(13) 0.3739(2) 0.02858(18) 0.0477(5) Uani d . 1 . .
O O3B 0.2609(3) 0.4930(2) 0.1701(3) 0.0570(10) Uani d . 1 . .
O O4B 0.14771(13) 0.6268(2) 0.0699(2) 0.0493(5) Uani d . 1 . .
H H44 0.1067 0.6000 0.1100 0.074 Uiso d R 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
_geom_angle_publ_flag
C1A N1A H22 . . 109.5 ?
C1A N1A H33 . . 109.5 ?
H22 N1A H33 . . 109.5 ?
C1A N1A H11 . . 109.5 ?
H22 N1A H11 . . 109.5 ?
H33 N1A H11 . . 109.5 ?
C6A C1A C2A . . 121.4(3) ?
C6A C1A N1A . . 120.3(3) ?
C2A C1A N1A . . 118.4(3) ?
C3A C2A C1A . . 118.2(3) ?
C3A C2A H2A . . 120.9 ?
C1A C2A H2A . . 120.9 ?
C2A C3A C4A . . 120.9(3) ?
C2A C3A H3A . . 119.6 ?
C4A C3A H3A . . 119.6 ?
C5A C4A C3A . . 119.4(3) ?
C5A C4A H4A . . 120.3 ?
C3A C4A H4A . . 120.3 ?
C4A C5A C6A . . 120.5(3) ?
C4A C5A H5A . . 119.8 ?
C6A C5A H5A . . 119.8 ?
C1A C6A C5A . . 119.6(3) ?
C1A C6A H6A . . 120.2 ?
C5A C6A H6A . . 120.2 ?
C1B N1B H1 . . 109.5 ?
C1B N1B H2 . . 109.5 ?
H1 N1B H2 . . 109.5 ?
C1B N1B H3 . . 109.5 ?
H1 N1B H3 . . 109.5 ?
H2 N1B H3 . . 109.5 ?
C2B C1B C6B . . 121.2(3) ?
C2B C1B N1B . . 119.8(3) ?
C6B C1B N1B . . 119.0(3) ?
C1B C2B C3B . . 118.8(3) ?
C1B C2B H2B . . 120.6 ?
C3B C2B H2B . . 120.6 ?
C4B C3B C2B . . 120.2(3) ?
C4B C3B H3B . . 119.9 ?
C2B C3B H3B . . 119.9 ?
C3B C4B C5B . . 120.7(4) ?
C3B C4B H4B . . 119.7 ?
C5B C4B H4B . . 119.7 ?
C4B C5B C6B . . 119.4(3) ?
C4B C5B H5B . . 120.3 ?
C6B C5B H5B . . 120.3 ?
C1B C6B C5B . . 119.7(3) ?
C1B C6B H6B . . 120.2 ?
C5B C6B H6B . . 120.2 ?
O1A S1A O2A . . 113.28(16) ?
O1A S1A O3A . . 114.1(2) ?
O2A S1A O3A . . 112.27(15) ?
O1A S1A O4A . . 103.72(14) ?
O2A S1A O4A . . 107.62(12) ?
O3A S1A O4A . . 104.85(16) ?
S1A O4A H4 . . 109.5 ?
O1B S1B O2B . . 113.68(16) ?
O1B S1B O3B . . 113.0(2) ?
O2B S1B O3B . . 111.55(14) ?
O1B S1B O4B . . 103.86(13) ?
O2B S1B O4B . . 107.56(12) ?
O3B S1B O4B . . 106.47(17) ?
S1B O4B H44 . . 109.5 ?
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
N1A C1A . 1.462(4) ?
N1A H22 . 0.8900 ?
N1A H33 . 0.8900 ?
N1A H11 . 0.8900 ?
C1A C6A . 1.361(5) ?
C1A C2A . 1.385(5) ?
C2A C3A . 1.380(5) ?
C2A H2A . 0.9300 ?
C3A C4A . 1.380(6) ?
C3A H3A . 0.9300 ?
C4A C5A . 1.372(6) ?
C4A H4A . 0.9300 ?
C5A C6A . 1.375(4) ?
C5A H5A . 0.9300 ?
C6A H6A . 0.9300 ?
N1B C1B . 1.460(3) ?
N1B H1 . 0.8900 ?
N1B H2 . 0.8900 ?
N1B H3 . 0.8900 ?
C1B C2B . 1.371(4) ?
C1B C6B . 1.378(4) ?
C2B C3B . 1.386(6) ?
C2B H2B . 0.9300 ?
C3B C4B . 1.373(6) ?
C3B H3B . 0.9300 ?
C4B C5B . 1.374(6) ?
C4B H4B . 0.9300 ?
C5B C6B . 1.380(4) ?
C5B H5B . 0.9300 ?
C6B H6B . 0.9300 ?
S1A O1A . 1.435(2) ?
S1A O2A . 1.436(2) ?
S1A O3A . 1.463(4) ?
S1A O4A . 1.554(2) ?
O4A H4 . 0.8201 ?
S1B O1B . 1.431(2) ?
S1B O2B . 1.4430(19) ?
S1B O3B . 1.448(4) ?
S1B O4B . 1.550(2) ?
O4B H44 . 0.8200 ?
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
N1A H11 O1A 4_465 0.890 1.946 2.821(2) 167.38
N1B H2 O3A 2_665 0.890 2.046 2.867(3) 152.79
N1A H33 O2B 3_555 0.890 2.006 2.884(3) 168.60
N1B H3 O1A . 0.890 2.583 3.069(3) 115.14
N1B H3 O2A . 0.890 2.029 2.916(3) 174.49
N1A H22 O3B . 0.890 1.953 2.817(4) 163.16
O4A H4 O3B . 0.820 1.786 2.603(4) 174.56
O4B H44 O3A 4_465 0.820 1.841 2.635(4) 162.51
N1B H1 O1B 2_665 0.890 1.941 2.828(3) 174.68
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
C6A C1A C2A C3A . . . . 0.9(5) ?
N1A C1A C2A C3A . . . . -179.6(3) ?
C1A C2A C3A C4A . . . . -0.7(5) ?
C2A C3A C4A C5A . . . . 0.0(6) ?
C3A C4A C5A C6A . . . . 0.4(6) ?
C2A C1A C6A C5A . . . . -0.4(5) ?
N1A C1A C6A C5A . . . . -180.0(3) ?
C4A C5A C6A C1A . . . . -0.2(5) ?
C6B C1B C2B C3B . . . . -0.4(4) ?
N1B C1B C2B C3B . . . . -178.8(3) ?
C1B C2B C3B C4B . . . . 0.9(4) ?
C2B C3B C4B C5B . . . . -1.6(5) ?
C3B C4B C5B C6B . . . . 1.7(6) ?
C2B C1B C6B C5B . . . . 0.5(5) ?
N1B C1B C6B C5B . . . . 178.9(3) ?
C4B C5B C6B C1B . . . . -1.1(5) ?
