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#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/08/2240871.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_2240871
loop_
_publ_author_name
'Dickinson, Sean R.'
'Müller, Peter'
'Tanski, Joseph M.'
_publ_section_title
;
 Crystal structure of 3-bromo-2-hydroxybenzonitrile
;
_journal_coeditor_code           LD2134
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o523
_journal_page_last               o524
_journal_paper_doi               10.1107/S2056989015011974
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C7 H4 Br N O'
_chemical_formula_moiety         'C7 H4 Br N O'
_chemical_formula_sum            'C7 H4 Br N O'
_chemical_formula_weight         198.02
_chemical_name_common            3-bromo-2-hydroxybenzonitrile
_chemical_name_systematic
;
3-Bromo-2-hydroxybenzonitrile
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 96.0620(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0171(7)
_cell_length_b                   3.8488(2)
_cell_length_c                   13.5989(7)
_cell_measurement_reflns_used    6401
_cell_measurement_temperature    125.(2)
_cell_measurement_theta_max      30.4951
_cell_measurement_theta_min      3.0127
_cell_volume                     677.50(6)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
SHELXTL2014 (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL2014 (Sheldrick, 2008), OLEX2 (Dolomanov et al.,
2009) and Mercury
(Macrae et al.,  2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      125.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0253
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9903
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    5.984
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.941
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.447
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1977
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0203
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0241P)²+0.2328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0474
_refine_ls_wR_factor_ref         0.0491
_reflns_number_gt                1776
_reflns_number_total             1977
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ld2134sup1.cif
_cod_data_source_block           I
_cod_database_code               2240871
_cod_database_fobs_code          2240871
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 0.70927(9) 0.4093(4) 0.76425(9) 0.0264(3) Uani d 1.0 . .
H H1 0.6483(13) 0.420(6) 0.7450(18) 0.04 Uiso d 1.0 . .
C C1 0.66122(12) 0.6091(4) 0.92251(12) 0.0195(3) Uani d 1.0 . .
C C7 0.5648(2) 0.7338(8) 0.8786(2) 0.0225(6) Uani d 0.9272(13) A 1
N N1 0.4862(2) 0.8421(7) 0.84343(18) 0.0281(5) Uani d 0.9272(13) A 1
Br Br1A 0.5216(4) 0.7707(10) 0.8684(3) 0.0332(13) Uani d 0.0728(13) A 2
C C2 0.73013(11) 0.4575(4) 0.86256(11) 0.0185(3) Uani d 1.0 . .
C C3 0.82692(11) 0.3564(4) 0.90818(11) 0.0186(3) Uani d 1.0 . .
Br Br1 0.92397(2) 0.15982(5) 0.82834(2) 0.02008(6) Uani d 0.9272(13) A 1
C C7A 0.8979(14) 0.192(6) 0.8577(15) 0.02008(6) Uani d 0.0728(13) A 2
N N1A 0.9658(13) 0.131(5) 0.8138(13) 0.02008(6) Uani d 0.0728(13) A 2
C C4 0.85334(13) 0.3982(4) 1.00854(12) 0.0234(3) Uani d 1.0 . .
H H4 0.9194 0.3259 1.0376 0.028 Uiso calc 1.0 . .
C C5 0.78350(14) 0.5460(5) 1.06728(12) 0.0267(3) Uani d 1.0 . .
H H5 0.8017 0.5739 1.1363 0.032 Uiso calc 1.0 . .
C C6 0.68739(13) 0.6519(4) 1.02446(12) 0.0237(3) Uani d 1.0 . .
H H6 0.6394 0.7532 1.064 0.028 Uiso calc 1.0 . .
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'
Br Br -0.2901 2.4595 '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 O1 H1 113.7(18)
C2 C1 C6 121.38(14)
C2 C1 C7 119.29(17)
C6 C1 C7 119.28(17)
C2 C1 Br1A 122.09(17)
C6 C1 Br1A 116.52(16)
N1 C7 C1 178.7(4)
O1 C2 C3 118.60(14)
O1 C2 C1 124.04(14)
C3 C2 C1 117.35(14)
C7A C3 C4 116.1(9)
C7A C3 C2 122.2(9)
C4 C3 C2 121.62(15)
C4 C3 Br1 119.86(12)
C2 C3 Br1 118.52(11)
N1A C7A C3 164.(3)
C3 C4 C5 120.30(15)
C3 C4 H4 119.9
C5 C4 H4 119.9
C6 C5 C4 119.63(15)
C6 C5 H5 120.2
C4 C5 H5 120.2
C5 C6 C1 119.71(16)
C5 C6 H6 120.1
C1 C6 H6 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3487(19)
O1 H1 0.810(16)
C1 C2 1.401(2)
C1 C6 1.402(2)
C1 C7 1.416(3)
C1 Br1A 1.988(5)
C7 N1 1.161(4)
C2 C3 1.400(2)
C3 C7A 1.363(14)
C3 C4 1.381(2)
C3 Br1 1.9071(16)
C7A N1A 1.143(16)
C4 C5 1.393(2)
C4 H4 0.95
C5 C6 1.384(2)
C5 H5 0.95
C6 H6 0.95
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_646 0.810(16) 2.038(18) 2.810(3) 159.(2) y
O1 H1 Br1A . 0.810(16) 2.82(2) 3.262(5) 116.(2) y
O1 H1 Br1A 2_646 0.810(16) 2.621(19) 3.379(5) 156.(2) 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 O1 179.94(15)
C7 C1 C2 O1 -2.6(3)
Br1A C1 C2 O1 0.4(3)
C6 C1 C2 C3 -1.2(2)
C7 C1 C2 C3 176.33(18)
Br1A C1 C2 C3 179.33(18)
O1 C2 C3 C7A -4.1(13)
C1 C2 C3 C7A 176.9(13)
O1 C2 C3 C4 -179.97(15)
C1 C2 C3 C4 1.1(2)
O1 C2 C3 Br1 0.5(2)
C1 C2 C3 Br1 -178.46(11)
C4 C3 C7A N1A -88.(8)
C2 C3 C7A N1A 96.(8)
C7A C3 C4 C5 -176.5(12)
C2 C3 C4 C5 -0.4(2)
Br1 C3 C4 C5 179.11(13)
C3 C4 C5 C6 -0.2(3)
C4 C5 C6 C1 0.1(3)
C2 C1 C6 C5 0.6(2)
C7 C1 C6 C5 -176.89(19)
Br1A C1 C6 C5 -179.86(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 12468680
