##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_journal_date_recd_electronic     2022-01-12
_journal_date_accepted     2022-01-31
_journal_name_full     'IUCrData'
_journal_year     2022
_journal_volume     7
_journal_issue      2
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314622001122
_journal_coeditor_code     VM4050
_publ_contact_author_name     'BENAROUS, N.'
_publ_contact_author_address
;
Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale \
 (CHEMS), Département de Chimie, Université des Frères Mentouri,
Constantine-1,
25017 Constantine,
Algeria
;
_publ_contact_author_email     nesrine.benarous@umc.edu.dz
_publ_contact_author_phone     '+213661906720'
_publ_section_title
;
2-Hydroxybenzenaminium acetate
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Moussa Slimane, Nabila' .
;
Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale \
 (CHEMS), Département de Chimie, Université des Frères Mentouri,
Constantine-1,
25017 Constantine,
Algeria
;
    'Benarous, Nesrine' .
;
Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale \
 (CHEMS), Département de Chimie, Université des Frères Mentouri,
Constantine-1,
25017 Constantine,
Algeria
;
    'Bougueria, Hassiba' .
;
Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale \
 (CHEMS), Département de Chimie, Université des Frères Mentouri,
Constantine-1,
25017 Constantine,
Algeria
Centre Universitaire Abd El Hafid Boussouf
Mila, 43000 Mila,
Algeria
;
    'Cherouana, Aouatef' .
;
Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale \
 (CHEMS), Département de Chimie, Université des Frères Mentouri,
Constantine-1,
25017 Constantine,
Algeria
;
_publ_section_synopsis
;
In the crystal, the molecules are linked by strong O---H...O and N---H...O
hydrogen bonds into supramolecular chains propagating along the b-axis
direction.
;
_chemical_name_systematic
;
2-Hydroxybenzenaminium acetate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H8 N O +, C2 H3 O2 -'
_chemical_formula_sum     'C8 H11 N O3'
_chemical_formula_iupac     'C6 H8 N O +, C2 H3 O2 -'
_chemical_formula_weight     169.18
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/c 1'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     9.9150(2)
_cell_length_b     7.2523(2)
_cell_length_c     11.9573(3)
_cell_angle_alpha     90
_cell_angle_beta     98.558(2)
_cell_angle_gamma     90
_cell_volume     850.23(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     52927
_cell_measurement_theta_min     3.3
_cell_measurement_theta_max     33.0
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.1
_exptl_crystal_size_mid     0.1
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.322
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     360
_exptl_absorpt_coefficient_mu     0.102
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details
;
(ABSORB; DeTitta, 1985)
;
_exptl_absorpt_correction_T_min     0.966
_exptl_absorpt_correction_T_max     0.991
_diffrn_ambient_temperature     100(2)
_diffrn_source     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     ?
_diffrn_measurement_device     'Oxford Diffraction Xcalibur Sapphire2 CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     52913
_diffrn_reflns_av_R_equivalents     0.0381
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_theta_min     3.295
_diffrn_reflns_theta_max     32.976
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.971
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     18
_refine_special_details
;
 The hydrogen atoms of the NH₃ and hydroxyl groups were localized in
the difference-Fourier map and refined with Uiso(H) set to
1.5Ueq(O) or 1.2Ueq(N). All the other hydrogen atoms were
placed in calculated positions with C---H = 0.95 Å for aromatic CH and C---H
= 0.96 Å for CH₃ and refined using a riding model with fixed isotropic
displacement parameters [Uiso(H) = 1.2Ueq(C-aromatic) and
Uiso(H) = 1.5Ueq(C-methyl)].
;
_reflns_number_total     3105
_reflns_number_gt     2736
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0431
_refine_ls_R_factor_gt     0.0375
_refine_ls_wR_factor_gt     0.1029
_refine_ls_wR_factor_ref     0.1087
_refine_ls_goodness_of_fit_ref     1.046
_refine_ls_restrained_S_all     1.046
_refine_ls_number_reflns     3105
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0542P)²+0.3200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.485
_refine_diff_density_min     -0.269
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_structure_solution
;
SHELXS  (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.12872(6) 0.83288(9) 0.65994(5) 0.01629(13) Uani d 1 . .
    H H1 0.1381(14) 0.928(2) 0.6142(12) 0.024 Uiso d 1 . .
    O O2 0.09592(7) 0.29888(8) 0.65411(5) 0.01686(13) Uani d 1 . .
    O O3 0.15033(7) 0.10731(8) 0.52349(5) 0.01664(13) Uani d 1 . .
    N N1 0.12133(7) 0.56570(9) 0.81635(5) 0.01242(13) Uani d 1 . .
    H H1A 0.1133(12) 0.4870(19) 0.7543(10) 0.015 Uiso d 1 . .
    H H1B 0.0461(12) 0.6407(18) 0.8160(10) 0.015 Uiso d 1 . .
    H H1C 0.1280(12) 0.4909(18) 0.8806(10) 0.015 Uiso d 1 . .
    C C3 0.35594(9) 0.93249(12) 0.74235(7) 0.01774(16) Uani d 1 . .
    H H3 0.358215 1.025256 0.686567 0.021 Uiso calc 1 . .
    C C5 0.46510(9) 0.77468(13) 0.90970(8) 0.01994(17) Uani d 1 . .
    H H5 0.540747 0.760726 0.967953 0.024 Uiso calc 1 . .
    C C4 0.46648(9) 0.91021(13) 0.82754(8) 0.02042(17) Uani d 1 . .
    H H4 0.543738 0.988327 0.829677 0.025 Uiso calc 1 . .
    C C2 0.24139(8) 0.81883(11) 0.73847(6) 0.01328(14) Uani d 1 . .
    C C6 0.35205(8) 0.65957(12) 0.90596(7) 0.01606(15) Uani d 1 . .
    H H6 0.350402 0.566114 0.961414 0.019 Uiso calc 1 . .
    C C1 0.24197(8) 0.68208(10) 0.82091(6) 0.01217(14) Uani d 1 . .
    C C8 0.13683(8) 0.26870(11) 0.56096(6) 0.01288(14) Uani d 1 . .
    C C7 0.16938(9) 0.42886(12) 0.48900(8) 0.01940(16) Uani d 1 . .
    H H7A 0.096016 0.443787 0.425025 0.029 Uiso calc 1 . .
    H H7B 0.255531 0.405118 0.460661 0.029 Uiso calc 1 . .
    H H7C 0.177717 0.541719 0.534587 0.029 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    O1 H1 . 0.892(14) ?
    O1 C2 . 1.3520(9) ?
    O2 C8 . 1.2600(9) ?
    O3 C8 . 1.2675(9) ?
    N1 H1A . 0.930(13) ?
    N1 H1B . 0.922(13) ?
    N1 H1C . 0.935(12) ?
    N1 C1 . 1.4583(10) ?
    C3 H3 . 0.9500 ?
    C3 C4 . 1.3903(12) ?
    C3 C2 . 1.3985(11) ?
    C5 H5 . 0.9500 ?
    C5 C4 . 1.3912(13) ?
    C5 C6 . 1.3930(12) ?
    C4 H4 . 0.9500 ?
    C2 C1 . 1.3978(11) ?
    C6 H6 . 0.9500 ?
    C6 C1 . 1.3863(11) ?
    C8 C7 . 1.5087(11) ?
    C7 H7A . 0.9800 ?
    C7 H7B . 0.9800 ?
    C7 H7C . 0.9800 ?
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
    C2 O1 H1 . . 109.4(9) ?
    H1A N1 H1B . . 112.7(11) ?
    H1A N1 H1C . . 106.7(11) ?
    H1B N1 H1C . . 107.7(10) ?
    C1 N1 H1A . . 110.9(8) ?
    C1 N1 H1B . . 108.5(8) ?
    C1 N1 H1C . . 110.3(7) ?
    C4 C3 H3 . . 119.9 ?
    C4 C3 C2 . . 120.24(8) ?
    C2 C3 H3 . . 119.9 ?
    C4 C5 H5 . . 120.2 ?
    C4 C5 C6 . . 119.55(8) ?
    C6 C5 H5 . . 120.2 ?
    C3 C4 C5 . . 120.66(8) ?
    C3 C4 H4 . . 119.7 ?
    C5 C4 H4 . . 119.7 ?
    O1 C2 C3 . . 124.17(7) ?
    O1 C2 C1 . . 117.36(7) ?
    C1 C2 C3 . . 118.48(7) ?
    C5 C6 H6 . . 120.2 ?
    C1 C6 C5 . . 119.66(8) ?
    C1 C6 H6 . . 120.2 ?
    C2 C1 N1 . . 117.84(7) ?
    C6 C1 N1 . . 120.74(7) ?
    C6 C1 C2 . . 121.40(7) ?
    O2 C8 O3 . . 122.53(7) ?
    O2 C8 C7 . . 119.65(7) ?
    O3 C8 C7 . . 117.81(7) ?
    C8 C7 H7A . . 109.5 ?
    C8 C7 H7B . . 109.5 ?
    C8 C7 H7C . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
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
    O1 C2 C1 N1 . . . . -0.22(10) ?
    O1 C2 C1 C6 . . . . -178.85(7) ?
    C3 C2 C1 N1 . . . . 179.48(7) ?
    C3 C2 C1 C6 . . . . 0.85(12) ?
    C5 C6 C1 N1 . . . . -178.83(7) ?
    C5 C6 C1 C2 . . . . -0.24(12) ?
    C4 C3 C2 O1 . . . . 178.84(8) ?
    C4 C3 C2 C1 . . . . -0.83(12) ?
    C4 C5 C6 C1 . . . . -0.39(13) ?
    C2 C3 C4 C5 . . . . 0.22(13) ?
    C6 C5 C4 C3 . . . . 0.40(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
    _geom_hbond_publ_flag
    O1 H1 O3 1_565 0.894(14) 1.709(14) 2.6025(9) 177.8(16) yes
    N1 H1A O2 . 0.930(13) 1.807(13) 2.7251(9) 168.7(12) yes
    N1 H1B O2 2_556 0.923(12) 1.891(12) 2.8019(9) 168.8(11) yes
    N1 H1C O3 4_566 0.935(12) 1.834(12) 2.7531(8) 167.2(12) yes
    C6 H6 O3 4_566 0.95 2.55 3.2493(11) 131 yes
_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.
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
