#------------------------------------------------------------------------------
#$Date: 2022-05-17 12:24:48 +0300 (Tue, 17 May 2022) $
#$Revision: 275488 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105285.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_8105285
loop_
_publ_author_name
'Chai, Chun-Xia'
'Peng, Peng'
'Cai, Bin'
_publ_section_title
;
 The crystal structure of 4,4′-bipyridinium
 bis(3-carboxy-2-nitrobenzoate) tetrahydrate, C13H13N2O8
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              779
_journal_page_last               781
_journal_paper_doi               10.1515/ncrs-2020-0004
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C8 H4 N O6, 0.5(C10 H10 N2), 2(H2 O)'
_chemical_formula_sum            'C13 H13 N2 O8'
_chemical_formula_weight         325.26
_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
_cell_angle_alpha                66.950(3)
_cell_angle_beta                 71.558(3)
_cell_angle_gamma                77.203(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8590(6)
_cell_length_b                   9.3108(8)
_cell_length_c                   11.0816(8)
_cell_measurement_reflns_used    5413
_cell_measurement_temperature    149(2)
_cell_measurement_theta_max      26.337
_cell_measurement_theta_min      2.393
_cell_volume                     703.38(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015) [1]'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015) [1]'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009) [3]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) [3]'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015) [4]'
_computing_structure_solution    'ShelXT (Sheldrick, 2015) [2]'
_diffrn_ambient_temperature      149.44
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9976
_diffrn_measurement_device       'Bruker APEX-II diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14035
_diffrn_reflns_theta_full        25.1855
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0677 before and 0.0518 after correction.
The Ratio of minimum to maximum transmission is 0.9317.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.5356
_exptl_crystal_description       needle
_exptl_crystal_F_000             338.2484
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.2750
_refine_diff_density_min         -0.3218
_refine_diff_density_rms         0.0606
_refine_ls_d_res_high            0.8351
_refine_ls_d_res_low             9.8574
_refine_ls_goodness_of_fit_ref   1.0544
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0544
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0555P)²+0.2935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1075
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -8
_reflns_limit_k_max              11
_reflns_limit_k_min              -10
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2059
_reflns_number_total             2535
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            suppl_ncrs-2020-0004_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105285
_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 Free rotating group:
 O2W(H2Wa,H2Wb,O1W,H1Wa,H1Wb)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), N2(H2)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
C1 C 0.2590(2) 0.7332(2) 0.13143(17) 0.0239(4) Uani 1.000000 .
C2 C 0.1192(2) 0.6259(2) 0.22712(16) 0.0205(4) Uani 1.000000 .
C3 C -0.0630(2) 0.6799(2) 0.24016(17) 0.0233(4) Uani 1.000000 .
H3 H -0.0978(2) 0.7835(2) 0.18540(17) 0.0280(5) Uiso 1.000000 R
C4 C -0.1942(2) 0.5853(2) 0.33159(18) 0.0253(4) Uani 1.000000 .
H4 H -0.3182(2) 0.6236(2) 0.33907(18) 0.0304(5) Uiso 1.000000 R
C5 C -0.1443(2) 0.4343(2) 0.41248(17) 0.0219(4) Uani 1.000000 .
H5 H -0.2351(2) 0.3703(2) 0.47605(17) 0.0263(5) Uiso 1.000000 R
C6 C 0.0367(2) 0.37510(19) 0.40201(16) 0.0186(4) Uani 1.000000 .
C7 C 0.1659(2) 0.47334(19) 0.30822(16) 0.0185(4) Uani 1.000000 .
C8 C 0.0840(2) 0.2093(2) 0.49207(17) 0.0215(4) Uani 1.000000 .
C9 C -0.0006(2) 0.58106(19) 0.94973(16) 0.0187(4) Uani 1.000000 .
C10 C -0.1603(2) 0.6787(2) 0.93760(18) 0.0251(4) Uani 1.000000 .
H10 H -0.2723(2) 0.6437(2) 0.99619(18) 0.0301(5) Uiso 1.000000 R
C11 C -0.1554(3) 0.8259(2) 0.84055(19) 0.0285(4) Uani 1.000000 .
H11 H -0.2654(3) 0.8917(2) 0.83241(19) 0.0342(5) Uiso 1.000000 R
C12 C 0.1539(3) 0.7897(2) 0.7685(2) 0.0352(5) Uani 1.000000 .
H12 H 0.2638(3) 0.8295(2) 0.7102(2) 0.0423(6) Uiso 1.000000 R
C13 C 0.1584(3) 0.6403(2) 0.8630(2) 0.0346(5) Uani 1.000000 .
H13 H 0.2708(3) 0.5776(2) 0.8688(2) 0.0416(6) Uiso 1.000000 R
N1 N 0.35924(19) 0.41137(17) 0.29123(15) 0.0232(3) Uani 1.000000 .
N2 N -0.0012(2) 0.87890(17) 0.75764(15) 0.0266(4) Uani 1.000000 .
H2 H -0.0020(2) 0.97335(17) 0.69541(15) 0.0319(4) Uiso 1.000000 R
O1 O 0.18947(19) 0.86345(16) 0.05184(14) 0.0363(4) Uani 1.000000 .
H1 H 0.2726(3) 0.9172(13) -0.0038(16) 0.0545(5) Uiso 1.000000 GR
O2 O 0.41792(18) 0.70310(16) 0.12970(13) 0.0336(3) Uani 1.000000 .
O3 O -0.04938(18) 0.14733(15) 0.58489(13) 0.0344(3) Uani 1.000000 .
O4 O 0.24093(17) 0.14612(15) 0.47314(14) 0.0325(3) Uani 1.000000 .
O5 O 0.43726(17) 0.41781(16) 0.36757(13) 0.0311(3) Uani 1.000000 .
O6 O 0.42763(17) 0.35738(17) 0.20058(14) 0.0353(3) Uani 1.000000 .
O2W O 0.41799(18) 0.05078(16) 0.87492(10) 0.0342(3) Uani 1.000000 .
H2Wa H 0.4567(19) 0.1279(11) 0.8807(2) 0.0513(5) Uiso 1.000000 G
H2Wb H 0.44643(16) 0.06749(13) 0.78837(10) 0.0513(5) Uiso 1.000000 G
O1W O 0.5133(2) 0.09097(19) 0.61236(11) 0.0507(5) Uani 1.000000 G
H1Wa H 0.4306(3) 0.1042(18) 0.5710(4) 0.0761(7) Uiso 1.000000 G
H1Wb H 0.5976(14) 0.0250(11) 0.5836(3) 0.0761(7) Uiso 1.000000 G
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
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'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 0.215599998832
'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 0.250800013542
'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 -11.5290002823
'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
O1 C1 C2 112.39(15) . .
O2 C1 C2 123.49(16) . .
O2 C1 O1 124.11(16) . .
C3 C2 C1 119.92(15) . .
C7 C2 C1 121.87(15) . .
C7 C2 C3 118.17(15) . .
H3 C3 C2 119.52(10) . .
C4 C3 C2 120.95(16) . .
C4 C3 H3 119.52(10) . .
H4 C4 C3 120.09(10) . .
C5 C4 C3 119.83(16) . .
C5 C4 H4 120.09(10) . .
H5 C5 C4 119.45(10) . .
C6 C5 C4 121.09(16) . .
C6 C5 H5 119.45(9) . .
C7 C6 C5 117.67(15) . .
C8 C6 C5 119.02(15) . .
C8 C6 C7 123.31(15) . .
C6 C7 C2 122.29(15) . .
N1 C7 C2 118.86(14) . .
N1 C7 C6 118.82(14) . .
O3 C8 C6 113.99(15) . .
O4 C8 C6 120.52(15) . .
O4 C8 O3 125.49(16) . .
C13 C9 C10 117.33(16) . .
H10 C10 C9 120.20(10) . .
C11 C10 C9 119.59(17) . .
C11 C10 H10 120.20(11) . .
H11 C11 C10 119.10(11) . .
N2 C11 C10 121.80(17) . .
N2 C11 H11 119.10(10) . .
C13 C12 H12 119.46(12) . .
N2 C12 H12 119.46(11) . .
N2 C12 C13 121.08(18) . .
C12 C13 C9 120.14(18) . .
H13 C13 C9 119.93(10) . .
H13 C13 C12 119.93(12) . .
O5 N1 C7 118.30(14) . .
O6 N1 C7 116.58(14) . .
O6 N1 O5 125.12(15) . .
C12 N2 C11 120.04(16) . .
H2 N2 C11 119.98(10) . .
H2 N2 C12 119.98(11) . .
H1 O1 C1 109.5 . .
H2Wb O2W H2Wa 104.5 . .
H1Wb O1W H1Wa 104.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.500(2) .
C1 O1 1.312(2) .
C1 O2 1.214(2) .
C2 C3 1.389(2) .
C2 C7 1.392(2) .
C3 H3 0.9500 .
C3 C4 1.381(2) .
C4 H4 0.9500 .
C4 C5 1.388(2) .
C5 H5 0.9500 .
C5 C6 1.392(2) .
C6 C7 1.395(2) .
C6 C8 1.514(2) .
C7 N1 1.481(2) .
C8 O3 1.269(2) .
C8 O4 1.234(2) .
C9 C9 1.484(3) 2_567
C9 C10 1.387(2) .
C9 C13 1.385(3) .
C10 H10 0.9500 .
C10 C11 1.371(3) .
C11 H11 0.9500 .
C11 N2 1.327(2) .
C12 H12 0.9500 .
C12 C13 1.376(3) .
C12 N2 1.326(3) .
C13 H13 0.9500 .
N1 O5 1.2164(18) .
N1 O6 1.2185(19) .
N2 H2 0.8800 .
O1 H1 0.8400 .
O2W H2Wa 0.8699 .
O2W H2Wb 0.8700 .
O1W H1Wa 0.8700 .
O1W H1Wb 0.8700 .
