#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/41/2214165.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_2214165
loop_
_publ_author_name
'Nourredine Benali-Cherif'
'Alima Kateb'
'Houda Boussekine'
'Zina Boutobba'
'Amel Messai'
_publ_section_title
;
 3-Hydroxyanilinium hydrogensulfate
;
_journal_coeditor_code           DN2197
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3251
_journal_page_last               o3251
_journal_paper_doi               10.1107/S1600536807028978
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C6 H8 N O + , H S1 O4 -'
_chemical_formula_moiety         'C6 H8 N O + , H O4 S -'
_chemical_formula_sum            'C6 H9 N O5 S'
_chemical_formula_weight         207.21
_chemical_name_common            'p-Hydroxyanilinium bisulfate'
_chemical_name_systematic
;
3-Hydroxyanilinium hydrogensulfate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.829(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3142(3)
_cell_length_b                   5.8612(2)
_cell_length_c                   9.8969(2)
_cell_measurement_reflns_used    5862
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.95
_cell_measurement_theta_min      2.08
_cell_volume                     419.25(2)
_computing_cell_refinement
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1998)'
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       ω/θ
_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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5851
_diffrn_reflns_theta_full        29.95
_diffrn_reflns_theta_max         29.95
_diffrn_reflns_theta_min         2.08
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.376
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.446
_refine_ls_abs_structure_details 'Flack (1983), with 1095 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2241
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0303
_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)+(0.0598P)²+0.051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                2150
_reflns_number_total             2241
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2197.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2214165
_cod_database_fobs_code          2214165
loop_
_symmetry_equiv_pos_as_xyz
'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
C C1 0.2336(2) 0.1606(4) 0.28583(15) 0.0237(3) Uani d . 1
C C2 0.3143(3) 0.3498(4) 0.35270(18) 0.0280(4) Uani d . 1
H H2 0.3587 0.4675 0.3037 0.034 Uiso calc R 1
C C3 0.3287(3) 0.3631(3) 0.49435(19) 0.0281(4) Uani d . 1
H H3 0.3824 0.4902 0.5408 0.034 Uiso calc R 1
C C4 0.2629(2) 0.1865(4) 0.56539(15) 0.0249(3) Uani d . 1
C C5 0.1808(3) -0.0052(4) 0.4976(2) 0.0310(4) Uani d . 1
H H5 0.1367 -0.1234 0.5463 0.037 Uiso calc R 1
C C6 0.1661(3) -0.0165(4) 0.35594(19) 0.0297(4) Uani d . 1
H H6 0.1112 -0.1424 0.3088 0.036 Uiso calc R 1
N N1 0.2226(2) 0.1419(3) 0.13659(15) 0.0271(3) Uani d . 1
H H1A 0.2343 0.2798 0.1012 0.041 Uiso calc R 1
H H1B 0.1137 0.0826 0.1011 0.041 Uiso calc R 1
H H1C 0.3130 0.0520 0.1171 0.041 Uiso calc R 1
O O41 0.2772(3) 0.1876(3) 0.70515(13) 0.0385(3) Uani d . 1
H H41 0.2966 0.3181 0.7336 0.058 Uiso calc R 1
O O2 0.8476(2) 0.0097(3) 0.04947(17) 0.0373(4) Uani d . 1
O O1 0.8468(2) 0.3880(3) 0.13117(15) 0.0333(3) Uani d . 1
H H1 0.8085 0.4545 0.1941 0.050 Uiso calc R 1
O O3 0.5869(2) 0.2501(3) -0.03018(17) 0.0474(5) Uani d . 1
O O4 0.6326(2) 0.1115(3) 0.20212(15) 0.0334(3) Uani d . 1
S S1 0.71804(5) 0.17750(8) 0.08525(3) 0.02299(12) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0227(6) 0.0291(9) 0.0187(6) 0.0027(8) 0.0019(5) -0.0021(7)
C2 0.0348(10) 0.0259(9) 0.0246(8) -0.0047(8) 0.0085(7) 0.0005(7)
C3 0.0340(9) 0.0245(9) 0.0260(8) -0.0040(7) 0.0056(7) -0.0035(7)
C4 0.0294(7) 0.0255(8) 0.0202(6) 0.0047(9) 0.0046(5) -0.0006(8)
C5 0.0390(10) 0.0290(10) 0.0253(8) -0.0072(8) 0.0061(7) 0.0017(7)
C6 0.0341(10) 0.0280(10) 0.0261(8) -0.0056(8) 0.0015(7) -0.0035(7)
N1 0.0283(6) 0.0325(10) 0.0202(6) 0.0031(7) 0.0029(5) -0.0008(6)
O41 0.0659(9) 0.0314(7) 0.0192(5) -0.0074(9) 0.0092(5) -0.0022(6)
O2 0.0310(7) 0.0397(9) 0.0432(8) 0.0016(7) 0.0120(6) -0.0167(7)
O1 0.0339(7) 0.0315(8) 0.0366(7) -0.0064(6) 0.0115(6) -0.0055(6)
O3 0.0462(9) 0.0469(9) 0.0423(8) -0.0053(8) -0.0144(7) 0.0167(7)
O4 0.0407(7) 0.0331(8) 0.0303(6) -0.0025(6) 0.0176(6) 0.0004(5)
S1 0.02315(18) 0.0258(2) 0.02035(18) 0.00081(18) 0.00441(12) 0.00186(16)
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
C2 C1 C6 121.59(15)
C2 C1 N1 119.74(18)
C6 C1 N1 118.66(18)
C1 C2 C3 119.31(17)
C1 C2 H2 120.3
C3 C2 H2 120.3
C4 C3 C2 119.56(17)
C4 C3 H3 120.2
C2 C3 H3 120.2
O41 C4 C3 122.2(2)
O41 C4 C5 116.7(2)
C3 C4 C5 121.13(16)
C6 C5 C4 118.94(19)
C6 C5 H5 120.5
C4 C5 H5 120.5
C1 C6 C5 119.47(18)
C1 C6 H6 120.3
C5 C6 H6 120.3
C1 N1 H1A 109.5
C1 N1 H1B 109.5
H1A N1 H1B 109.5
C1 N1 H1C 109.5
H1A N1 H1C 109.5
H1B N1 H1C 109.5
C4 O41 H41 109.5
S1 O1 H1 109.5
O3 S1 O2 112.88(11)
O3 S1 O4 113.33(10)
O2 S1 O4 113.12(10)
O3 S1 O1 107.06(10)
O2 S1 O1 102.60(9)
O4 S1 O1 106.89(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.377(3)
C1 C6 1.382(3)
C1 N1 1.4709(19)
C2 C3 1.392(3)
C2 H2 0.9300
C3 C4 1.379(3)
C3 H3 0.9300
C4 O41 1.3710(18)
C4 C5 1.396(3)
C5 C6 1.391(3)
C5 H5 0.9300
C6 H6 0.9300
N1 H1A 0.8900
N1 H1B 0.8900
N1 H1C 0.8900
O41 H41 0.8200
O2 S1 1.4467(16)
O1 S1 1.5759(15)
O1 H1 0.8200
O3 S1 1.4389(15)
O4 S1 1.4491(14)
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 H1A O2 2_655 0.89 2.03 2.830(2) 148.9
N1 H1B O2 1_455 0.89 1.98 2.853(2) 165.9
N1 H1C O3 2_645 0.89 2.14 2.962(2) 152.4
N1 H1C O4 . 0.89 2.39 2.975(2) 123.9
O41 H41 O4 2_656 0.82 1.88 2.695(2) 174.0
O1 H1 O41 2_656 0.82 1.86 2.642(2) 160.2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 40390
