#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/92/2019233.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_2019233
loop_
_publ_author_name
'Thomas, Lynne H.'
'Adam, Martin S.'
'O'Neill, Andrew'
'Wilson, Chick C.'
_publ_section_title
;
 Utilizing proton transfer to produce molecular salts in bromanilic acid
 substituted-pyridine molecular complexes -- predictable synthons?
;
_journal_coeditor_code           FM3015
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1279
_journal_page_last               1288
_journal_paper_doi               10.1107/S0108270113029533
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C6 H6 Br N , C6 H2 Br2 O4'
_chemical_formula_moiety         'C6 H6 Br N, C6 H2 Br2 O4'
_chemical_formula_sum            'C12 H8 Br3 N O4'
_chemical_formula_weight         469.91
_chemical_name_systematic
;
2-Bromo-3-methylpyridine--bromanilic acid (1/1)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.556(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2866(3)
_cell_length_b                   13.3814(8)
_cell_length_c                   20.3576(13)
_cell_measurement_temperature    100(2)
_cell_volume                     1439.61(15)
_computing_cell_refinement       'APEX2 (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'APEX2 (Bruker, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14350
_diffrn_reflns_theta_full        27.24
_diffrn_reflns_theta_max         27.24
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    8.42
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.465046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Blessing, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.168
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.672
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0324P)²+0.0000P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0861
_reflns_number_gt                2267
_reflns_number_total             3202
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fm3015.cif
_cod_data_source_block           ba_2br3mepyr
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2019233
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.6951(8) 0.5218(3) 0.4532(2) 0.0142(10) Uani d . 1 1
C C3 0.6017(8) 0.5990(3) 0.4964(2) 0.0153(10) Uani d . 1 1
C C2 0.6005(8) 0.4285(3) 0.4553(2) 0.0134(10) Uani d . 1 1
O O1 0.6758(6) 0.3552(2) 0.41693(17) 0.0226(8) Uani d D 1 1
O O2 0.6701(6) 0.6863(2) 0.49613(16) 0.0244(8) Uani d . 1 1
Br Br1 0.95526(9) 0.55598(3) 0.39596(2) 0.01783(14) Uani d . 1 1
C C4 0.6894(8) 0.0737(3) 0.5152(2) 0.0149(10) Uani d . 1 1
C C6 0.5333(8) 0.0834(3) 0.4566(2) 0.0148(10) Uani d . 1 1
C C5 0.3339(8) 0.0032(3) 0.4423(2) 0.0141(10) Uani d . 1 1
O O3 0.1920(6) 0.0119(2) 0.38894(16) 0.0188(8) Uani d . 1 1
O O4 0.5461(6) 0.1528(2) 0.41714(16) 0.0190(7) Uani d . 1 1
Br Br2 0.93951(9) 0.17269(3) 0.52850(2) 0.01781(14) Uani d . 1 1
C C7 0.3385(8) 0.1755(3) 0.2548(2) 0.0169(11) Uani d . 1 1
C C8 0.3281(9) 0.2589(4) 0.2135(2) 0.0205(11) Uani d . 1 1
C C9 0.1496(9) 0.3294(4) 0.2290(2) 0.0244(12) Uani d . 1 1
H H9 0.1296 0.3858 0.2027 0.029 Uiso calc R 1 1
C C10 0.0000(9) 0.3180(3) 0.2830(2) 0.0239(12) Uani d . 1 1
H H10 -0.1194 0.3661 0.2933 0.029 Uiso calc R 1 1
C C11 0.0310(9) 0.2333(4) 0.3214(2) 0.0233(12) Uani d . 1 1
H H11 -0.0658 0.2259 0.3586 0.028 Uiso calc R 1 1
N N1 0.1966(7) 0.1620(3) 0.30642(18) 0.0161(9) Uani d . 1 1
C C12 0.4994(9) 0.2719(4) 0.1563(2) 0.0308(13) Uani d . 1 1
H H12A 0.4070 0.2577 0.1162 0.046 Uiso calc R 1 1
H H12B 0.6400 0.2268 0.1609 0.046 Uiso calc R 1 1
H H12C 0.5604 0.3394 0.1554 0.046 Uiso calc R 1 1
Br Br3 0.56870(10) 0.06825(4) 0.23905(3) 0.02778(16) Uani d . 1 1
H H1 0.601(8) 0.301(2) 0.427(2) 0.033 Uiso d D 1 1
H H2 0.227(10) 0.064(4) 0.361(3) 0.042(17) Uiso d . 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 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.011 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.29 2.46 '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
C2 C1 C3 . . 120.5(4)
C2 C1 Br1 . . 121.6(3)
C3 C1 Br1 . . 117.9(3)
O2 C3 C1 . . 124.9(4)
O2 C3 C2 . 3_666 116.6(4)
C1 C3 C2 . 3_666 118.5(4)
O1 C2 C1 . . 123.4(4)
O1 C2 C3 . 3_666 115.6(4)
C1 C2 C3 . 3_666 121.0(4)
C2 O1 H1 . . 110(4)
C5 C4 C6 3_656 . 122.7(4)
C5 C4 Br2 3_656 . 121.2(3)
C6 C4 Br2 . . 116.1(3)
O4 C6 C4 . . 124.7(4)
O4 C6 C5 . . 117.1(4)
C4 C6 C5 . . 118.2(4)
O3 C5 C4 . 3_656 122.6(4)
O3 C5 C6 . . 118.3(4)
C4 C5 C6 3_656 . 119.1(4)
C5 O3 H2 . . 117(3)
N1 C7 C8 . . 125.1(4)
N1 C7 Br3 . . 114.1(3)
C8 C7 Br3 . . 120.9(4)
C9 C8 C7 . . 115.2(4)
C9 C8 C12 . . 121.9(4)
C7 C8 C12 . . 122.9(4)
C8 C9 C10 . . 121.2(5)
C8 C9 H9 . . 119.4
C10 C9 H9 . . 119.4
C9 C10 C11 . . 118.7(5)
C9 C10 H10 . . 120.7
C11 C10 H10 . . 120.7
N1 C11 C10 . . 121.6(5)
N1 C11 H11 . . 119.2
C10 C11 H11 . . 119.2
C7 N1 C11 . . 118.3(4)
C8 C12 H12A . . 109.5
C8 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
C8 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.346(6)
C1 C3 . 1.453(6)
C1 Br1 . 1.882(4)
C3 O2 . 1.223(5)
C3 C2 3_666 1.517(6)
C2 O1 . 1.322(5)
C2 C3 3_666 1.517(6)
O1 H1 . 0.857(19)
C4 C5 3_656 1.353(6)
C4 C6 . 1.437(6)
C4 Br2 . 1.886(4)
C6 O4 . 1.230(5)
C6 C5 . 1.527(6)
C5 O3 . 1.308(5)
C5 C4 3_656 1.353(6)
O3 H2 . 0.92(5)
C7 N1 . 1.321(6)
C7 C8 . 1.397(6)
C7 Br3 . 1.914(4)
C8 C9 . 1.378(7)
C8 C12 . 1.504(7)
C9 C10 . 1.379(7)
C9 H9 . 0.9300
C10 C11 . 1.384(6)
C10 H10 . 0.9300
C11 N1 . 1.336(6)
C11 H11 . 0.9300
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
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
O1 H1 O4 . 0.857(19) 2.01(3) 2.794(4) 151(5)
O1 H1 O2 3_666 0.857(19) 2.15(5) 2.638(5) 115(4)
O3 H2 N1 . 0.92(5) 1.73(5) 2.619(5) 163(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139061682
