##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_journal_date_recd_electronic     2023-09-12
_journal_date_accepted     2023-09-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2023
_journal_volume     79
_journal_issue     11
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989023008460
_journal_coeditor_code     WM5697
_publ_contact_author_name     'Valerii Y. Sirenko'
_publ_contact_author_address
;
Department of Chemistry,
Taras Shevchenko National University of Kyiv
Volodymyrska St. 64
Kyiv 01601
Ukraine
;
_publ_contact_author_email     valerii_sirenko@knu.ua
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Crystal structure of bis(3-carboxy-1-methylpyridinium) octabromide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Sirenko, Valerii Y.' .
;
Department of Chemistry,
Taras Shevchenko National University of Kyiv, Volodymyrska St. 64/13,
Kyiv 01601,
Ukraine
;
    'Naumova, Dina D.' .
;
Department of Chemistry,
Taras Shevchenko National University of Kyiv, Volodymyrska St. 64/13,
Kyiv 01601,
Ukraine
;
    'Golenya, Irina A.' .
;
Department of Chemistry,
Taras Shevchenko National University of Kyiv, Volodymyrska St. 64/13,
Kyiv 01601,
Ukraine
;
    'Shova, Sergiu' .
;
Department of Inorganic Polymers,
"Petru Poni" Institute of Macromolecular Chemistry,
Romanian Academy of Science,
Aleea Grigore Ghica Voda 41A,
Iasi 700487,
Romania
;
    'Gural'skiy, Il'ya A.' .
;
Department of Chemistry,
Taras Shevchenko National University of Kyiv, Volodymyrska St. 64/13,
Kyiv 01601,
Ukraine
;
_publ_section_synopsis
;
The structure of the title compound is composed of rare Z-shaped
octabromide anions embedded within N-methylnicotinic acid cations.
;
_chemical_name_systematic
;
Bis(3-carboxy-1-methylpyridinium) octabromide
;
_chemical_formula_moiety     '2(C7 H8 N O2 +), Br8 2-'
_chemical_formula_sum     'C14 H16 Br8 N2 O4'
_chemical_formula_iupac     '2C7 H8 N O2 +, Br8 2-'
_chemical_formula_weight     915.522
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_id
    _space_group_symop_operation_xyz
    1 x,y,z
    2 -x,-y,-z
_cell_length_a     6.8537(5)
_cell_length_b     7.0873(6)
_cell_length_c     14.5145(6)
_cell_angle_alpha     95.746(5)
_cell_angle_beta     91.156(4)
_cell_angle_gamma     115.002(7)
_cell_volume     634.23(8)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     2335
_cell_measurement_theta_min     3.1900
_cell_measurement_theta_max     23.7360
_cell_measurement_temperature     293
_exptl_crystal_description     block
_exptl_crystal_colour     'light red'
_exptl_crystal_size_max     0.17
_exptl_crystal_size_mid     0.11
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     2.397
_exptl_crystal_F_000     424.594
_exptl_absorpt_coefficient_mu     12.666
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_absorpt_correction_T_min     0.45777
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     293.00
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Xcalibur, Eos'
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     16.1593
_diffrn_reflns_number     9457
_diffrn_reflns_av_R_equivalents     0.0483
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_theta_min     2.83
_diffrn_reflns_theta_max     29.31
_diffrn_reflns_theta_full     25.2417
_diffrn_measured_fraction_theta_max     0.8636
_diffrn_measured_fraction_theta_full     0.9996
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_reflns_number_total     3008
_reflns_number_gt     1848
_reflns_threshold_expression     I>=2u(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0975
_refine_ls_R_factor_gt     0.0473
_refine_ls_wR_factor_gt     0.0620
_refine_ls_wR_factor_ref     0.0748
_refine_ls_goodness_of_fit_ref     1.0231
_refine_ls_restrained_S_all     1.0229
_refine_ls_number_reflns     3008
_refine_ls_number_parameters     132
_refine_ls_number_restraints     1
_refine_ls_number_constraints     13
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0186P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     -0.0014
_refine_ls_shift/su_mean     0.0001
_refine_diff_density_max     1.3755
_refine_diff_density_min     -1.3169
_refine_ls_extinction_method     'SHELXL'
_refine_ls_extinction_coef     0.0112(5)
_refine_ls_extinction_expression
                                    Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
loop_
    _atom_type_symbol
    _atom_type_scat_Cromer_Mann_a1
    _atom_type_scat_Cromer_Mann_a2
    _atom_type_scat_Cromer_Mann_a3
    _atom_type_scat_Cromer_Mann_a4
    _atom_type_scat_Cromer_Mann_b1
    _atom_type_scat_Cromer_Mann_b2
    _atom_type_scat_Cromer_Mann_b3
    _atom_type_scat_Cromer_Mann_b4
    _atom_type_scat_Cromer_Mann_c
    _atom_type_scat_dispersion_source
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    Br 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090 41.43280
                                                                         2.95570
  'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850' -0.38188 2.46625
                     'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
    C 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870 51.65120 0.21560
 'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850' 0.00313 0.00162
                     'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
    H 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236 57.79970 0.00304
 'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850' 0.00000 0.00000
                     'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
    N 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750 0.58260
                                                                       -11.52900
  'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850' 0.00612 0.00332
                     'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
    O 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390 32.90890 0.25080
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850' 0.01085 0.00610
                     'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015)
;
_computing_structure_refinement
;
olex2.refine (Bourhis et al.,  2015)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 (Dolomanov et al.,  2009)
;
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_occupancy
    Br Br2 0.06745(8) 0.45917(8) 0.30515(3) 0.05120(19) Uani 1.000000
    Br Br3 -0.18168(9) 0.43980(10) 0.15210(3) 0.0628(2) Uani 1.000000
    Br Br1 0.29688(10) 0.47662(9) 0.43679(4) 0.0673(2) Uani 1.000000
    Br Br4 -0.04755(10) 0.12253(10) 0.04613(3) 0.0781(3) Uani 1.000000
    O O1 0.9137(6) 0.8874(6) 0.3821(2) 0.0564(10) Uani 1.000000
    O O2 0.7895(5) 1.0613(5) 0.4839(2) 0.0540(10) Uani 1.000000
    N N1 0.4595(6) 0.8218(6) 0.1811(2) 0.0420(10) Uani 1.000000
    C C2 0.6297(7) 0.9597(7) 0.3314(3) 0.0348(12) Uani 1.000000
    C C6 0.7873(8) 0.9736(8) 0.4062(3) 0.0430(13) Uani 1.000000
    C C1 0.6035(7) 0.8341(7) 0.2488(3) 0.0423(13) Uani 1.000000
    H H1a 0.6851(7) 0.7580(7) 0.2398(3) 0.0507(15) Uiso 1.000000
    C C4 0.3646(8) 1.0582(8) 0.2730(3) 0.0477(13) Uani 1.000000
    H H4 0.2828(8) 1.1345(8) 0.2802(3) 0.0572(16) Uiso 1.000000
    C C5 0.3421(8) 0.9306(8) 0.1928(3) 0.0497(14) Uani 1.000000
    H H5 0.2430(8) 0.9193(8) 0.1454(3) 0.0597(17) Uiso 1.000000
    C C3 0.5093(8) 1.0726(8) 0.3430(3) 0.0444(13) Uani 1.000000
    H H3 0.5259(8) 1.1585(8) 0.3981(3) 0.0533(16) Uiso 1.000000
    C C7 0.4279(8) 0.6816(8) 0.0942(3) 0.0660(17) Uani 1.000000
    H H7a 0.508(4) 0.600(4) 0.1002(9) 0.099(3) Uiso 1.000000
    H H7b 0.2774(10) 0.589(4) 0.0823(13) 0.099(3) Uiso 1.000000
    H H7c 0.477(5) 0.7640(9) 0.0437(5) 0.099(3) Uiso 1.000000
    H H1 0.992(7) 0.879(9) 0.426(3) 0.099(3) Uiso 1.000000
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
    Br2 Br3 . 2.7307(7) ?
    Br2 Br1 . 2.4095(7) ?
    Br3 Br4 . 3.0625(10) ?
    Br1 Br1 2_666 3.1813(12) ?
    Br4 Br4 2 2.4002(15) ?
    O1 C6 . 1.290(6) ?
    O1 H1 . 0.845(19) ?
    O2 C6 . 1.228(5) ?
    N1 C1 . 1.348(5) ?
    N1 C5 . 1.332(6) ?
    N1 C7 . 1.476(5) ?
    C2 C6 . 1.483(6) ?
    C2 C1 . 1.380(6) ?
    C2 C3 . 1.373(6) ?
    C1 H1a . 0.9300 ?
    C4 H4 . 0.9300 ?
    C4 C5 . 1.365(6) ?
    C4 C3 . 1.370(6) ?
    C5 H5 . 0.9300 ?
    C3 H3 . 0.9300 ?
    C7 H7a . 0.9600 ?
    C7 H7b . 0.9600 ?
    C7 H7c . 0.9600 ?
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
    Br1 Br2 Br3 . . 178.04(3) ?
    Br4 Br3 Br2 . . 90.37(2) ?
    Br1 Br1 Br2 2_666 . 162.42(4) ?
    Br4 Br4 Br3 2 . 176.22(3) ?
    H1 O1 C6 . . 116(4) ?
    C5 N1 C1 . . 120.7(4) ?
    C7 N1 C1 . . 119.4(4) ?
    C7 N1 C5 . . 119.8(4) ?
    C1 C2 C6 . . 120.3(5) ?
    C3 C2 C6 . . 120.6(4) ?
    C3 C2 C1 . . 119.2(4) ?
    O2 C6 O1 . . 125.2(4) ?
    C2 C6 O1 . . 114.6(4) ?
    C2 C6 O2 . . 120.1(5) ?
    C2 C1 N1 . . 120.0(5) ?
    H1a C1 N1 . . 120.0(3) ?
    H1a C1 C2 . . 120.0(3) ?
    C5 C4 H4 . . 120.4(3) ?
    C3 C4 H4 . . 120.4(3) ?
    C3 C4 C5 . . 119.2(5) ?
    C4 C5 N1 . . 121.2(4) ?
    H5 C5 N1 . . 119.4(3) ?
    H5 C5 C4 . . 119.4(3) ?
    C4 C3 C2 . . 119.8(4) ?
    H3 C3 C2 . . 120.1(3) ?
    H3 C3 C4 . . 120.1(3) ?
    H7a C7 N1 . . 109.5 ?
    H7b C7 N1 . . 109.5 ?
    H7b C7 H7a . . 109.5 ?
    H7c C7 N1 . . 109.5 ?
    H7c C7 H7a . . 109.5 ?
    H7c C7 H7b . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C6 C2 C1 . . . . 9.9(5) ?
    O1 C6 C2 C3 . . . . -169.6(4) ?
    O2 C6 C2 C1 . . . . -169.9(4) ?
    O2 C6 C2 C3 . . . . 10.6(5) ?
    N1 C1 C2 C6 . . . . 179.8(4) ?
    N1 C1 C2 C3 . . . . -0.6(5) ?
    N1 C5 C4 C3 . . . . -0.7(6) ?
    C2 C3 C4 C5 . . . . 0.3(5) ?
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 O2 2_776 0.80(7) 1.89(7) 2.668(5) 164(7) yes
    C1 H1A Br3 1_655 0.93 2.96 3.838(5) 158.1 yes
    C5 H5 Br4 2_565 0.93 2.99 3.881(5) 160.0 yes
    C7 H7A Br3 1_655 0.96 2.92 3.857(6) 166.0 yes
