#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/20/2222016.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_2222016
loop_
_publ_author_name
'Thomas, Lynne H.'
'Boyle, Bryan'
'Clive, Lesley A.'
'Collins, Anna'
'Currie, Lynsey D.'
'Gogol, Malgorzata'
'Hastings, Claire'
'Jones, Andrew O. F.'
'Kennedy, Jennifer L.'
'Kerr, Graham B.'
'Kidd, Alastair'
'Lawton, Lorreta M.'
'Macintyre, Susan J.'
'MacLean, Niall M.'
'Martin, Alan R. G.'
'McGonagle, Kate'
'Melrose, Samantha'
'Rew, Gaius A.'
'Robinson, Colin W.'
'Schmidtmann, Marc'
'Turnbull, Felicity B.'
'Williams, Lewis G.'
'Wiseman, Alan Y.'
'Wocial, Malgorzata H.'
'Wilson, Chick C.'
_publ_section_title
;
 2-Acetylpyridinium bromanilate
;
_journal_coeditor_code           HB2948
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1218
_journal_paper_doi               10.1107/S1600536809016456
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C7 H8 N O +, C6 H Br2 O4 -'
_chemical_formula_moiety         'C7 H8 N O +, C6 H Br2 O4 -'
_chemical_formula_sum            'C13 H9 Br2 N O5'
_chemical_formula_weight         419.03
_chemical_name_systematic
;
2-Acetylpyridinium bromanilate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 112.396(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1323(5)
_cell_length_b                   13.3821(7)
_cell_length_c                   12.2287(7)
_cell_measurement_reflns_used    13698
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      55.21
_cell_measurement_theta_min      6.09
_cell_volume                     1381.74(13)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2008)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2008)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al.,  2006)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_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
;
Rigaku R-AXIS RAPID IP
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17193
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    5.887
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.561
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.014
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.307
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0216
_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)+(0.0229P)²+0.7894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0499
_reflns_number_gt                2793
_reflns_number_total             3156
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2948.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222016
_cod_database_fobs_code          2222016
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_disorder_assembly
_atom_site_disorder_group
H H6 0.611(3) 0.307(2) 0.195(3) 0.041(8) Uiso d . 1 . .
O O5 0.50649(17) 0.44777(11) 0.25644(13) 0.0201(3) Uani d . 1 . .
N N1 0.5396(2) 0.29814(12) 0.11977(16) 0.0152(3) Uani d . 1 . .
C C12 0.4282(2) 0.45501(15) 0.15172(18) 0.0160(4) Uani d . 1 . .
C C11 0.5549(2) 0.22016(16) 0.05849(19) 0.0200(4) Uani d . 1 . .
H H5 0.637(3) 0.1735(18) 0.102(2) 0.024 Uiso d . 1 . .
C C8 0.3294(2) 0.36207(16) -0.04572(18) 0.0173(4) Uani d . 1 . .
H H2 0.263(3) 0.4122(18) -0.076(2) 0.021 Uiso d . 1 . .
C C10 0.4555(3) 0.20854(17) -0.0595(2) 0.0223(5) Uani d . 1 . .
H H4 0.468(3) 0.156(2) -0.099(2) 0.027 Uiso d . 1 . .
C C7 0.4298(2) 0.37017(14) 0.07151(17) 0.0145(4) Uani d . 1 . .
C C9 0.3417(3) 0.28035(17) -0.11190(19) 0.0217(4) Uani d . 1 . .
H H3 0.274(3) 0.2759(19) -0.195(2) 0.026 Uiso d . 1 . .
C C13 0.3272(3) 0.54328(17) 0.0970(2) 0.0232(5) Uani d . 1 . .
H H9 0.351(3) 0.595(2) 0.152(2) 0.028 Uiso d . 1 . .
H H7 0.340(3) 0.5618(19) 0.027(2) 0.028 Uiso d . 1 . .
H H8 0.222(3) 0.5245(19) 0.076(2) 0.028 Uiso d . 1 . .
H H1 0.663(4) 0.511(2) 0.426(3) 0.050(10) Uiso d . 1 . .
Br Br1 0.92699(2) 0.416206(15) 0.738904(17) 0.01764(6) Uani d . 1 . .
Br Br2 0.98903(2) 0.811177(15) 0.427719(17) 0.01869(6) Uani d . 1 . .
O O1 1.19471(16) 0.56928(11) 0.79086(12) 0.0180(3) Uani d . 1 . .
O O2 1.22536(16) 0.73058(10) 0.67034(12) 0.0186(3) Uani d . 1 . .
O O3 0.73311(16) 0.64428(11) 0.37219(12) 0.0198(3) Uani d . 1 . .
C C5 0.9790(2) 0.69726(14) 0.51628(17) 0.0150(4) Uani d . 1 . .
O O4 0.70848(17) 0.48853(11) 0.48976(14) 0.0197(3) Uani d . 1 . .
C C1 0.8359(2) 0.54445(15) 0.54043(18) 0.0152(4) Uani d . 1 . .
C C6 0.8462(2) 0.63450(15) 0.46801(17) 0.0149(4) Uani d . 1 . .
C C4 1.1029(2) 0.67882(14) 0.62391(18) 0.0139(4) Uani d . 1 . .
C C3 1.0879(2) 0.58650(14) 0.69581(17) 0.0143(4) Uani d . 1 . .
C C2 0.9474(2) 0.52459(14) 0.64757(17) 0.0145(4) Uani d . 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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C11 N1 C7 . . 122.38(18) ?
C11 N1 H6 . . 119.2(18) ?
C7 N1 H6 . . 118.2(18) ?
O5 C12 C13 . . 123.61(19) ?
O5 C12 C7 . . 118.77(18) ?
C13 C12 C7 . . 117.62(18) ?
N1 C11 C10 . . 120.53(19) ?
N1 C11 H5 . . 115.3(15) ?
C10 C11 H5 . . 124.2(15) ?
C7 C8 C9 . . 119.83(19) ?
C7 C8 H2 . . 117.2(16) ?
C9 C8 H2 . . 122.9(16) ?
C9 C10 C11 . . 118.8(2) ?
C9 C10 H4 . . 122.0(16) ?
C11 C10 H4 . . 119.1(16) ?
N1 C7 C8 . . 119.03(18) ?
N1 C7 C12 . . 116.30(17) ?
C8 C7 C12 . . 124.67(18) ?
C10 C9 C8 . . 119.39(19) ?
C10 C9 H3 . . 120.6(15) ?
C8 C9 H3 . . 119.9(15) ?
C12 C13 H9 . . 109.4(16) ?
C12 C13 H7 . . 110.4(16) ?
H9 C13 H7 . . 112(2) ?
C12 C13 H8 . . 107.8(16) ?
H9 C13 H8 . . 110(2) ?
H7 C13 H8 . . 107(2) ?
C4 C5 C6 . . 123.42(18) ?
C4 C5 Br2 . . 119.00(14) ?
C6 C5 Br2 . . 117.57(14) ?
C1 O4 H1 . . 107(2) ?
O4 C1 C2 . . 123.31(19) ?
O4 C1 C6 . . 114.51(17) ?
C2 C1 C6 . . 122.18(17) ?
O3 C6 C5 . . 127.49(19) ?
O3 C6 C1 . . 114.86(17) ?
C5 C6 C1 . . 117.65(17) ?
O2 C4 C5 . . 126.44(18) ?
O2 C4 C3 . . 116.07(17) ?
C5 C4 C3 . . 117.48(17) ?
O1 C3 C2 . . 122.78(18) ?
O1 C3 C4 . . 118.58(17) ?
C2 C3 C4 . . 118.64(17) ?
C1 C2 C3 . . 120.51(18) ?
C1 C2 Br1 . . 121.41(15) ?
C3 C2 Br1 . . 118.08(14) ?
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
O5 C12 . 1.209(2) ?
N1 C11 . 1.323(3) ?
N1 C7 . 1.353(2) ?
N1 H6 . 0.91(3) ?
C12 C13 . 1.491(3) ?
C12 C7 . 1.504(3) ?
C11 C10 . 1.390(3) ?
C11 H5 . 0.96(3) ?
C8 C7 . 1.381(3) ?
C8 C9 . 1.390(3) ?
C8 H2 . 0.89(2) ?
C10 C9 . 1.381(3) ?
C10 H4 . 0.88(3) ?
C9 H3 . 0.97(3) ?
C13 H9 . 0.93(3) ?
C13 H7 . 0.94(3) ?
C13 H8 . 0.93(3) ?
Br1 C2 . 1.8826(19) ?
Br2 C5 . 1.8922(19) ?
O1 C3 . 1.221(2) ?
O2 C4 . 1.253(2) ?
O3 C6 . 1.239(2) ?
C5 C4 . 1.392(3) ?
C5 C6 . 1.407(3) ?
O4 C1 . 1.322(2) ?
O4 H1 . 0.79(3) ?
C1 C2 . 1.344(3) ?
C1 C6 . 1.520(3) ?
C4 C3 . 1.552(3) ?
C3 C2 . 1.451(3) ?
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
O4 H1 O5 . 0.78(3) 2.20(3) 2.798(2) 134(3)
N1 H6 O2 3_766 0.91(3) 1.83(3) 2.673(2) 154(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655785
2 PubChem 139076640
