#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/31/2233137.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_2233137
loop_
_publ_author_name
'Zipp, Caitlin F.'
'Fernandes, Manuel A.'
'Marques, Helder M.'
'Michael, Joseph P.'
_publ_section_title
;
 (2-Aminophenyl)methanol
;
_journal_coeditor_code           FJ2480
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o174
_journal_paper_doi               10.1107/S1600536811053657
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C7 H9 N O'
_chemical_formula_moiety         'C7 H9 N O'
_chemical_formula_sum            'C7 H9 N O'
_chemical_formula_weight         123.15
_chemical_name_systematic
;
(2-Aminophenyl)methanol
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.6222(9)
_cell_length_b                   6.0675(2)
_cell_length_c                   4.7005(2)
_cell_measurement_reflns_used    3105
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      3.48
_cell_volume                     645.19(4)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL99
(Keller, 1999)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0776
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4682
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         715
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0244P)²+0.1192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0754
_reflns_number_gt                681
_reflns_number_total             715
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2480.cif
_cod_data_source_block           I
_cod_database_code               2233137
_cod_database_fobs_code          2233137
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.38086(8) 0.4709(3) 0.5647(4) 0.0316(4) Uani d . 1 1
C C2 0.40551(8) 0.2625(3) 0.6243(5) 0.0306(4) Uani d . 1 1
C C3 0.37720(9) 0.1240(3) 0.8170(5) 0.0378(5) Uani d . 1 1
H H3 0.3938 -0.0161 0.8583 0.045 Uiso calc R 1 1
C C4 0.32549(9) 0.1866(3) 0.9489(6) 0.0443(5) Uani d . 1 1
H H4 0.3067 0.0889 1.0783 0.053 Uiso calc R 1 1
C C5 0.30074(9) 0.3917(4) 0.8937(6) 0.0450(5) Uani d . 1 1
H H5 0.2653 0.4364 0.9855 0.054 Uiso calc R 1 1
C C6 0.32908(9) 0.5302(3) 0.7009(5) 0.0383(5) Uani d . 1 1
H H6 0.3122 0.6704 0.6615 0.046 Uiso calc R 1 1
C C7 0.40968(8) 0.6224(3) 0.3546(5) 0.0348(5) Uani d . 1 1
H H7A 0.4151 0.5445 0.1714 0.042 Uiso calc R 1 1
H H7B 0.3839 0.7515 0.3207 0.042 Uiso calc R 1 1
N N1 0.45972(7) 0.1975(2) 0.5061(4) 0.0343(4) Uani d . 1 1
H H1A 0.4637 0.0557 0.4904 0.041 Uiso d R 1 1
H H1B 0.4735 0.2644 0.3450 0.041 Uiso d R 1 1
O O1 0.46612(5) 0.69530(18) 0.4600(3) 0.0350(4) Uani d . 1 1
H H1 0.4872 0.7176 0.3123 0.053 Uiso d R 1 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C6 C1 C2 118.46(17)
C6 C1 C7 120.94(16)
C2 C1 C7 120.59(17)
C3 C2 N1 119.38(16)
C3 C2 C1 119.25(18)
N1 C2 C1 121.26(16)
C4 C3 C2 121.18(18)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 120.3(2)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 118.5(2)
C4 C5 H5 120.8
C6 C5 H5 120.8
C1 C6 C5 122.29(18)
C1 C6 H6 118.9
C5 C6 H6 118.9
O1 C7 C1 110.35(17)
O1 C7 H7A 109.6
C1 C7 H7A 109.6
O1 C7 H7B 109.6
C1 C7 H7B 109.6
H7A C7 H7B 108.1
C2 N1 H1A 113.8
C2 N1 H1B 120.1
H1A N1 H1B 109.5
C7 O1 H1 105.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.383(3)
C1 C2 1.410(2)
C1 C7 1.498(3)
C2 C3 1.392(3)
C2 N1 1.403(2)
C3 C4 1.377(3)
C3 H3 0.9500
C4 C5 1.389(3)
C4 H4 0.9500
C5 C6 1.393(3)
C5 H5 0.9500
C6 H6 0.9500
C7 O1 1.439(2)
C7 H7A 0.9900
C7 H7B 0.9900
N1 H1A 0.8683
N1 H1B 0.9141
O1 H1 0.8534
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 N1 2_664 0.85 1.94 2.791(2) 172 y
N1 H1B O1 2_664 0.91 2.28 3.135(2) 156 y
N1 H1A O1 1_545 0.87 2.19 3.0585(17) 175 y
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 -0.1(3)
C7 C1 C2 C3 -178.96(19)
C6 C1 C2 N1 -176.24(17)
C7 C1 C2 N1 4.9(3)
N1 C2 C3 C4 176.60(19)
C1 C2 C3 C4 0.4(3)
C2 C3 C4 C5 -0.7(3)
C3 C4 C5 C6 0.6(3)
C2 C1 C6 C5 0.1(3)
C7 C1 C6 C5 179.0(2)
C4 C5 C6 C1 -0.3(3)
C6 C1 C7 O1 114.52(18)
C2 C1 C7 O1 -66.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20149
2 PubChem 21439
