#------------------------------------------------------------------------------
#$Date: 2023-12-07 13:50:03 +0200 (Thu, 07 Dec 2023) $
#$Revision: 288138 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022868.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_2022868
loop_
_publ_author_name
'Sirenko, Valerii Y.'
'Naumova, Dina D.'
'Golenya, Irina A.'
'Shova, Sergiu'
'Gural'skiy, Il'ya A.'
_publ_section_title
;
 Crystal structure of bis-(3-carb-oxy-1-methyl-pyrid-inium) octa-bromide.
;
_journal_coeditor_code           WM5697
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              977
_journal_page_last               981
_journal_paper_doi               10.1107/S2056989023008460
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          '2C7 H8 N O2 +, Br8 2-'
_chemical_formula_moiety         '2(C7 H8 N O2 +), Br8 2-'
_chemical_formula_sum            'C14 H16 Br8 N2 O4'
_chemical_formula_weight         915.522
_chemical_name_systematic
;
Bis(3-carboxy-1-methylpyridinium) octabromide
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_cell_angle_alpha                95.746(5)
_cell_angle_beta                 91.156(4)
_cell_angle_gamma                115.002(7)
_cell_formula_units_Z            1
_cell_length_a                   6.8537(5)
_cell_length_b                   7.0873(6)
_cell_length_c                   14.5145(6)
_cell_measurement_reflns_used    2335
_cell_measurement_temperature    293
_cell_measurement_theta_max      23.7360
_cell_measurement_theta_min      3.1900
_cell_volume                     634.23(8)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
olex2.refine (Bourhis et al.,  2015)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015)
;
_diffrn_ambient_temperature      293.00
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.8636
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9457
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.31
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    12.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            'light red'
_exptl_crystal_density_diffrn    2.397
_exptl_crystal_description       block
_exptl_crystal_F_000             424.594
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.3755
_refine_diff_density_min         -1.3169
_refine_ls_extinction_coef       0.0112(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.0231
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    13
_refine_ls_number_parameters     132
_refine_ls_number_reflns         3008
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0229
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          -0.0014
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0186P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0748
_reflns_number_gt                1848
_reflns_number_total             3008
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            wm5697sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022868.cif.'
_cod_database_code               2022868
_cod_database_fobs_code          2022868
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
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_
_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)'
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_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_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
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) ?
