#------------------------------------------------------------------------------
#$Date: 2022-05-11 10:40:56 +0300 (Wed, 11 May 2022) $
#$Revision: 275320 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105207.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_8105207
loop_
_publ_author_name
'Wei-Wei, Yuan'
_publ_section_title
;
 Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene
 bis(2-carboxy-4-bromobenzoate) -- water (1/4), C14H14BrNO6
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              289
_journal_page_last               291
_journal_paper_doi               10.1515/ncrs-2022-0002
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C8 H4 Br O4, 2(H2 O), C6 H6 N'
_chemical_formula_sum            'C14 H14 Br N O6'
_chemical_formula_weight         372.174
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_cell_angle_alpha                72.774(5)
_cell_angle_beta                 81.547(4)
_cell_angle_gamma                74.370(4)
_cell_formula_units_Z            2
_cell_length_a                   6.9693(3)
_cell_length_b                   8.6514(5)
_cell_length_c                   13.6726(8)
_cell_measurement_reflns_used    4076
_cell_measurement_temperature    290.7(3)
_cell_measurement_theta_max      25.0180
_cell_measurement_theta_min      4.0110
_cell_volume                     756.26(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.7(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9839
_diffrn_measured_fraction_theta_max 0.9839
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     -4.00  46.00   1.00    6.22    --   12.34  38.00  30.00   50
  2  ω     -2.00  80.00   1.00    6.22    --   12.34  57.00  60.00   82
  3  ω     13.00  80.00   1.00    6.22    --   12.34  57.00 -90.00   67
  4  ω     53.00  79.00   1.00    6.22    --   12.34  57.00-150.00   26
  5  ω     -3.00  79.00   1.00    6.22    --   12.34  57.00-180.00   82
  6  ω    -27.00  58.00   1.00    6.22    --  -11.32  38.00 -60.00   85
  7  ω    -20.00  30.00   1.00    6.22    --   12.34 -38.00  60.00   50
  8  ω    -20.00  51.00   1.00    6.22    --   12.34 -99.00  60.00   71
  9  ω     25.00  51.00   1.00    6.22    --   12.34 -99.00 -60.00   26
 10  ω    -20.00  51.00   1.00    6.22    --   12.34 -99.00-150.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0111924000
_diffrn_orient_matrix_UB_12      -0.0699951000
_diffrn_orient_matrix_UB_13      -0.0190924000
_diffrn_orient_matrix_UB_21      -0.0101405000
_diffrn_orient_matrix_UB_22      0.0532846000
_diffrn_orient_matrix_UB_23      -0.0505382000
_diffrn_orient_matrix_UB_31      0.1048850000
_diffrn_orient_matrix_UB_32      -0.0087339000
_diffrn_orient_matrix_UB_33      -0.0068687000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.9839
_diffrn_reflns_Laue_measured_fraction_max 0.9839
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9713
_diffrn_reflns_point_group_measured_fraction_full 0.9839
_diffrn_reflns_point_group_measured_fraction_max 0.9839
_diffrn_reflns_theta_full        24.9997
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.32
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.746
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_description       block
_exptl_crystal_F_000             375.870
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.6234
_refine_diff_density_min         -0.7303
_refine_diff_density_rms         0.0837
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             6.1386
_refine_ls_goodness_of_fit_ref   1.0562
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0562
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          -0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0236P)²+0.3771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0689
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              10
_reflns_limit_k_min              -9
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2234
_reflns_number_total             2621
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            suppl_j_ncrs-2022-0002_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105207
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O4(H4), O5(H5a,H5b), O6(H6a,H6b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), N1(H1), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.718
_oxdiff_exptl_absorpt_empirical_full_min 0.463
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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_refinement_flags_posn
Br1 Br 0.10135(5) 0.62802(4) 0.57890(2) 0.04918(13) Uani 1.000000 .
O1 O 0.4021(3) 0.2897(2) 0.55589(13) 0.0433(5) Uani 1.000000 .
O2 O 0.2047(3) 0.1116(3) 0.61415(15) 0.0521(6) Uani 1.000000 .
O3 O 0.2516(4) -0.0407(3) 1.00931(15) 0.0600(6) Uani 1.000000 .
O4 O 0.1305(4) 0.1745(3) 1.07727(15) 0.0700(7) Uani 1.000000 .
C1 C 0.1357(4) 0.4625(3) 0.70646(19) 0.0318(6) Uani 1.000000 .
C2 C 0.2069(4) 0.2941(3) 0.71165(18) 0.0296(6) Uani 1.000000 .
C3 C 0.2198(4) 0.1816(3) 0.80833(19) 0.0342(6) Uani 1.000000 .
C4 C 0.1690(4) 0.2335(4) 0.8977(2) 0.0380(7) Uani 1.000000 .
C5 C 0.0990(5) 0.4019(4) 0.8886(2) 0.0479(8) Uani 1.000000 .
C6 C 0.0806(4) 0.5160(4) 0.7944(2) 0.0443(7) Uani 1.000000 .
C7 C 0.2745(4) 0.2278(4) 0.61906(19) 0.0349(7) Uani 1.000000 .
C8 C 0.1889(5) 0.1069(4) 0.9995(2) 0.0451(8) Uani 1.000000 .
O5 O 0.1189(4) -0.0103(3) 1.26636(15) 0.0677(7) Uani 1.000000 .
O6 O 0.2807(3) -0.0038(3) 1.43460(15) 0.0555(6) Uani 1.000000 .
N1 N 0.4131(4) 0.4028(3) 0.35232(17) 0.0486(7) Uani 1.000000 .
C9 C 0.4855(5) 0.2857(4) 0.3028(2) 0.0575(9) Uani 1.000000 .
C10 C 0.5011(5) 0.3288(4) 0.1983(2) 0.0545(9) Uani 1.000000 .
C11 C 0.4431(4) 0.4952(4) 0.1430(2) 0.0375(7) Uani 1.000000 .
C12 C 0.3686(4) 0.6128(4) 0.1977(2) 0.0408(7) Uani 1.000000 .
C13 C 0.3559(4) 0.5634(4) 0.3032(2) 0.0447(7) Uani 1.000000 .
C14 C 0.4599(4) 0.5485(4) 0.03037(19) 0.0408(7) Uani 1.000000 .
H3 H 0.2636(4) 0.0682(3) 0.81343(19) 0.0411(8) Uiso 1.000000 R
H5 H 0.0636(5) 0.4387(4) 0.9476(2) 0.0575(9) Uiso 1.000000 R
H6 H 0.0313(4) 0.6289(4) 0.7898(2) 0.0532(9) Uiso 1.000000 R
H13 H 0.3074(4) 0.6423(4) 0.3402(2) 0.0536(9) Uiso 1.000000 R
H9 H 0.5255(5) 0.1746(4) 0.3395(2) 0.0690(11) Uiso 1.000000 R
H10 H 0.5507(5) 0.2468(4) 0.1637(2) 0.0655(10) Uiso 1.000000 R
H12 H 0.3273(4) 0.7249(4) 0.1632(2) 0.0489(9) Uiso 1.000000 R
H14 H 0.4094(4) 0.6608(4) -0.00082(19) 0.0490(8) Uiso 1.000000 R
H4 H 0.1201(4) 0.1047(3) 1.12950(15) 0.1050(11) Uiso 1.000000 R
H5a H 0.1742(4) -0.0071(3) 1.31692(15) 0.1015(10) Uiso 1.000000 R
H5b H 0.0178(4) -0.0490(3) 1.29344(15) 0.1015(10) Uiso 1.000000 R
H6a H 0.2478(3) 0.0208(3) 1.49150(15) 0.0832(9) Uiso 1.000000 R
H6b H 0.3776(3) -0.0893(3) 1.44727(15) 0.0832(9) Uiso 1.000000 R
H1 H 0.4028(4) 0.3736(3) 0.41835(17) 0.0583(8) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_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_source
_atom_type_scat_dispersion_source
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
H4 O4 C8 110.6 . .
C2 C1 Br1 121.8(2) . .
C6 C1 Br1 117.1(2) . .
C6 C1 C2 121.1(2) . .
C3 C2 C1 117.7(2) . .
C7 C2 C1 123.8(2) . .
C7 C2 C3 118.5(2) . .
C4 C3 C2 121.9(2) . .
H3 C3 C2 119.04(15) . .
H3 C3 C4 119.04(16) . .
C5 C4 C3 118.2(3) . .
C8 C4 C3 119.5(3) . .
C8 C4 C5 122.3(3) . .
C6 C5 C4 121.4(3) . .
H5 C5 C4 119.31(17) . .
H5 C5 C6 119.31(17) . .
C5 C6 C1 119.6(3) . .
H6 C6 C1 120.19(16) . .
H6 C6 C5 120.19(17) . .
O2 C7 O1 126.0(3) . .
C2 C7 O1 116.9(3) . .
C2 C7 O2 117.0(2) . .
O4 C8 O3 124.0(3) . .
C4 C8 O3 123.4(3) . .
C4 C8 O4 112.6(3) . .
H5b O5 H5a 104.5 . .
H6b O6 H6a 104.5 . .
C13 N1 C9 122.2(3) . .
H1 N1 C9 118.89(16) . .
H1 N1 C13 118.89(17) . .
C10 C9 N1 119.9(3) . .
H9 C9 N1 120.04(16) . .
H9 C9 C10 120.0(2) . .
C11 C10 C9 120.2(3) . .
H10 C10 C9 119.9(2) . .
H10 C10 C11 119.88(17) . .
C12 C11 C10 117.8(3) . .
C14 C11 C10 122.4(3) . .
C14 C11 C12 119.8(3) . .
C13 C12 C11 119.8(3) . .
H12 C12 C11 120.08(16) . .
H12 C12 C13 120.08(19) . .
C12 C13 N1 119.9(3) . .
H13 C13 N1 120.03(17) . .
H13 C13 C12 120.03(19) . .
C14 C14 C11 125.8(3) 2_665 .
H14 C14 C11 117.09(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.899(2) .
O1 C7 1.257(3) .
O2 C7 1.251(3) .
O3 C8 1.206(4) .
O4 C8 1.324(3) .
O4 H4 0.7956 .
C1 C2 1.391(4) .
C1 C6 1.381(4) .
C2 C3 1.389(3) .
C2 C7 1.504(4) .
C3 C4 1.389(4) .
C3 H3 0.9300 .
C4 C5 1.380(4) .
C4 C8 1.493(4) .
C5 C6 1.370(4) .
C5 H5 0.9300 .
C6 H6 0.9300 .
O5 H5a 0.8500 .
O5 H5b 0.8500 .
O6 H6a 0.8500 .
O6 H6b 0.8500 .
N1 C9 1.331(4) .
N1 C13 1.330(4) .
N1 H1 0.8600 .
C9 C10 1.361(4) .
C9 H9 0.9300 .
C10 C11 1.392(4) .
C10 H10 0.9300 .
C11 C12 1.385(4) .
C11 C14 1.467(4) .
C12 C13 1.374(4) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 C14 1.315(5) 2_665
C14 H14 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O5 0.7956 1.841(3) 2.609(3) 161.98(10) .
O5 H5a O6 0.8500 1.879(3) 2.727(3) 175.99(9) .
O5 H5b O2 0.8500 1.941(3) 2.767(3) 163.86(9) 2_557
O6 H6a O2 0.8500 2.006(3) 2.844(3) 168.52(9) 1_556
O6 H6b O1 0.8500 1.989(3) 2.823(3) 166.76(8) 2_657
N1 H1 O1 0.8600 1.804(3) 2.660(3) 173.22(11) .
