#------------------------------------------------------------------------------
#$Date: 2022-02-04 05:35:26 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272553 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/63/1566307.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_1566307
loop_
_publ_author_name
'Moussa Slimane, Nabila'
'Benarous, Nesrine'
'Bougueria, Hassiba'
'Cherouana, Aouatef'
_publ_section_title
;
 2-Hydroxybenzenaminium acetate
;
_journal_coeditor_code           VM4050
_journal_issue                   2
_journal_name_full               IUCrData
_journal_page_first              x220112
_journal_paper_doi               10.1107/S2414314622001122
_journal_volume                  7
_journal_year                    2022
_chemical_formula_iupac          'C6 H8 N O +, C2 H3 O2 -'
_chemical_formula_moiety         'C6 H8 N O +, C2 H3 O2 -'
_chemical_formula_sum            'C8 H11 N O3'
_chemical_formula_weight         169.18
_chemical_name_systematic
;
2-Hydroxybenzenaminium acetate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.558(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9150(2)
_cell_length_b                   7.2523(2)
_cell_length_c                   11.9573(3)
_cell_measurement_reflns_used    52927
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.0
_cell_measurement_theta_min      3.3
_cell_volume                     850.23(4)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS  (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'Oxford Diffraction Xcalibur Sapphire2 CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            52913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.976
_diffrn_reflns_theta_min         3.295
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(ABSORB; DeTitta, 1985)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0542P)²+0.3200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1087
_reflns_number_gt                2736
_reflns_number_total             3105
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm4050sup1.cif
_cod_data_source_block           I
_cod_database_code               1566307
_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.
;
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'
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 . .
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'
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_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_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
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) ?

_cod_database_fobs_code 1566307
