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#$Date: 2022-05-16 12:12:19 +0300 (Mon, 16 May 2022) $
#$Revision: 275449 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105271.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105271
loop_
_publ_author_name
'Li, Shu-Jing'
'Li, Ke'
'Li, Yi-Wen'
_publ_section_title
;
 The crystal structure of 3-bromoisonicotinic acid, C6H4BrNO2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              731
_journal_page_last               732
_journal_paper_doi               10.1515/ncrs-2019-0933
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C6 H4 Br N O2'
_chemical_formula_sum            'C6 H4 Br N O2'
_chemical_formula_weight         202.00
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                65.065(4)
_cell_angle_beta                 68.858(4)
_cell_angle_gamma                64.919(4)
_cell_formula_units_Z            2
_cell_length_a                   7.2512(6)
_cell_length_b                   7.3916(6)
_cell_length_c                   7.4920(7)
_cell_measurement_reflns_used    3527
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      3.18
_cell_volume                     321.60(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015) [1]'
_computing_data_collection       'Bruker APEX-II'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015) [1]'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009) [4]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) [4]'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015) [3]'
_computing_structure_solution    'ShelXT (Sheldrick, 2015) [2]'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker APEX-II diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7419
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         3.075
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.316
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1011 before and 0.0737 after correction.
The Ratio of minimum to maximum transmission is 0.6138.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.086
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.153
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0369
_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)+(0.0675P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1017
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1119
_reflns_number_total             1263
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0933_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105271
_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_max   0.571
_shelx_estimated_absorpt_t_min   0.301
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.31443(7) 0.07999(6) 0.77220(6) 0.0268(2) Uani 1 1 d . . . . .
C1 C 0.2434(6) 0.4894(6) 0.9021(6) 0.0156(8) Uani 1 1 d . . . . .
C2 C 0.2406(6) 0.5263(6) 0.6891(6) 0.0148(8) Uani 1 1 d . . . . .
C3 C 0.2684(6) 0.3667(6) 0.6160(6) 0.0141(8) Uani 1 1 d . . . . .
C4 C 0.2666(6) 0.4153(6) 0.4193(6) 0.0179(8) Uani 1 1 d . . . . .
H4 H 0.286606 0.305172 0.373367 0.021 Uiso 1 1 calc R . . . .
C5 C 0.2105(6) 0.7657(6) 0.3534(6) 0.0193(8) Uani 1 1 d . . . . .
H5 H 0.189642 0.905180 0.261850 0.023 Uiso 1 1 calc R . . . .
C6 C 0.2116(6) 0.7284(6) 0.5505(6) 0.0172(8) Uani 1 1 d . . . . .
H6 H 0.192299 0.841823 0.591350 0.021 Uiso 1 1 calc R . . . .
H1 H 0.274(10) 0.633(10) 1.046(10) 0.056(18) Uiso 1 1 d . . . . .
N1 N 0.2381(6) 0.6109(5) 0.2878(5) 0.0188(7) Uani 1 1 d . . . . .
O1 O 0.2623(5) 0.6511(5) 0.9162(5) 0.0257(7) Uani 1 1 d . . . . .
O2 O 0.2278(5) 0.3314(4) 1.0405(5) 0.0235(7) Uani 1 1 d . . . . .
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'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 C2 111.1(3) . .
O2 C1 C2 123.8(3) . .
O2 C1 O1 125.1(4) . .
C3 C2 C1 124.3(3) . .
C6 C2 C1 119.6(3) . .
C6 C2 C3 116.1(3) . .
C2 C3 Br1 124.4(3) . .
C4 C3 Br1 115.7(3) . .
C4 C3 C2 119.9(3) . .
C3 C4 H4 118.4 . .
N1 C4 C3 123.2(3) . .
N1 C4 H4 118.4 . .
C6 C5 H5 119.0 . .
N1 C5 H5 119.0 . .
N1 C5 C6 122.0(4) . .
C2 C6 H6 119.7 . .
C5 C6 C2 120.6(3) . .
C5 C6 H6 119.7 . .
C4 N1 C5 118.1(4) . .
C1 O1 H1 115(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C3 1.887(4) .
C1 C2 1.508(5) .
C1 O1 1.309(5) .
C1 O2 1.208(5) .
C2 C3 1.413(5) .
C2 C6 1.392(6) .
C3 C4 1.365(6) .
C4 H4 0.9500 .
C4 N1 1.340(5) .
C5 H5 0.9500 .
C5 C6 1.385(6) .
C5 N1 1.342(5) .
C6 H6 0.9500 .
O1 H1 0.96(7) .
