#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/59/2225940.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_2225940
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
'Young, David J.'
_publ_section_title
;
 Bis[2-(2,4-dinitrobenzyl)pyridinium] biphenyl-4,4'-disulfonate
 trihydrate
;
_journal_coeditor_code           NG2763
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1184
_journal_page_last               o1185
_journal_paper_doi               10.1107/S1600536810014819
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '2C12 H10 N3 O4 +, C12 H8 O6 S2 2-, 3H2 O'
_chemical_formula_moiety
'2(C12 H10 N3 O4 +), C12 H8 O6 S2 2-, 3(H2 O)'
_chemical_formula_sum            'C36 H34 N6 O17 S2'
_chemical_formula_weight         886.83
_chemical_melting_point          413
_chemical_name_systematic
;
Bis[2-(2,4-dinitrobenzyl)pyridinium] biphenyl-4,4'-disulfonate trihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                97.879(3)
_cell_angle_beta                 96.926(3)
_cell_angle_gamma                112.066(4)
_cell_formula_units_Z            1
_cell_length_a                   8.3897(3)
_cell_length_b                   10.6455(4)
_cell_length_c                   11.7405(5)
_cell_measurement_reflns_used    5908
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.29
_cell_measurement_theta_min      3.01
_cell_volume                     945.53(7)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection
'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)'
_computing_structure_solution
'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.08
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S CCD-detector diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8964
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         3.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.299
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         3844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0505P)²+0.4454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                3441
_reflns_number_total             3844
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2763.cif
_cod_data_source_block           I
_cod_database_code               2225940
_cod_database_fobs_code          2225940
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O21 0.5436(2) 0.07535(18) 0.71892(15) 0.0487(6) Uani . . 1.000
O O22 0.51554(19) 0.13704(18) 0.55354(14) 0.0460(5) Uani . . 1.000
O O41 0.9552(2) 0.10842(19) 0.32892(14) 0.0548(6) Uani . . 1.000
O O42 1.2220(2) 0.1865(2) 0.41565(15) 0.0627(7) Uani . . 1.000
N N1 0.7507(2) 0.15288(18) 1.02586(14) 0.0291(5) Uani . . 1.000
N N21 0.6039(2) 0.12314(17) 0.63793(15) 0.0319(5) Uani . . 1.000
N N41 1.0680(2) 0.15615(18) 0.41645(15) 0.0350(5) Uani . . 1.000
C C2 0.8078(2) 0.1261(2) 0.92656(16) 0.0276(5) Uani . . 1.000
C C3 0.8089(3) -0.0026(2) 0.89375(18) 0.0348(6) Uani . . 1.000
C C4 0.7505(3) -0.1008(2) 0.9630(2) 0.0403(7) Uani . . 1.000
C C5 0.6935(3) -0.0690(2) 1.06403(19) 0.0400(7) Uani . . 1.000
C C6 0.6954(3) 0.0601(2) 1.09439(18) 0.0364(7) Uani . . 1.000
C C11 0.9122(2) 0.21211(18) 0.74513(16) 0.0256(5) Uani . . 1.000
C C21 0.7921(2) 0.16202(18) 0.63956(16) 0.0260(5) Uani . . 1.000
C C31 0.8394(2) 0.14506(19) 0.53166(17) 0.0278(5) Uani . . 1.000
C C41 1.0145(2) 0.17560(19) 0.53089(16) 0.0275(5) Uani . . 1.000
C C51 1.1393(2) 0.2235(2) 0.63196(17) 0.0303(6) Uani . . 1.000
C C61 1.0871(2) 0.2431(2) 0.73779(17) 0.0291(6) Uani . . 1.000
C C71 0.8663(3) 0.2446(2) 0.86313(17) 0.0318(6) Uani . . 1.000
S S4A 0.60027(6) 0.49714(5) 0.81725(4) 0.0279(2) Uani . . 1.000
O O41A 0.71609(19) 0.57569(16) 0.92704(12) 0.0391(5) Uani . . 1.000
O O42A 0.51335(19) 0.35151(15) 0.81872(14) 0.0412(5) Uani . . 1.000
O O43A 0.4786(2) 0.55635(18) 0.77623(13) 0.0436(5) Uani . . 1.000
C C1A 0.9443(2) 0.50258(19) 0.54441(16) 0.0272(6) Uani . . 1.000
C C2A 0.7662(3) 0.4645(3) 0.51220(19) 0.0576(9) Uani . . 1.000
C C3A 0.6617(3) 0.4658(3) 0.59494(19) 0.0531(9) Uani . . 1.000
C C4A 0.7357(2) 0.50677(19) 0.71157(16) 0.0263(6) Uani . . 1.000
C C5A 0.9122(3) 0.5469(2) 0.74546(18) 0.0399(6) Uani . . 1.000
C C6A 1.0155(3) 0.5444(2) 0.66214(19) 0.0409(7) Uani . . 1.000
O O1W 0.7300(2) 0.39624(19) 1.07848(14) 0.0422(6) Uani . . 1.000
O O2W 0.4510(4) 0.7847(3) 0.7040(3) 0.0475(11) Uani . . 0.500
H H1 0.746(4) 0.240(3) 1.049(2) 0.059(8) Uiso . . 1.000
H H3 0.84830 -0.02380 0.82590 0.0420 Uiso calc R 1.000
H H4 0.75000 -0.18830 0.94090 0.0480 Uiso calc R 1.000
H H5 0.65440 -0.13420 1.11060 0.0480 Uiso calc R 1.000
H H6 0.65840 0.08380 1.16260 0.0440 Uiso calc R 1.000
H H31 0.75700 0.11440 0.46260 0.0330 Uiso calc R 1.000
H H51 1.25620 0.24210 0.62900 0.0360 Uiso calc R 1.000
H H61 1.17110 0.27820 0.80620 0.0350 Uiso calc R 1.000
H H71 0.96790 0.31920 0.91260 0.0380 Uiso calc R 1.000
H H72 0.77380 0.27800 0.85240 0.0380 Uiso calc R 1.000
H H2A 0.71510 0.43730 0.43320 0.0690 Uiso calc R 1.000
H H3A 0.54180 0.43900 0.57140 0.0640 Uiso calc R 1.000
H H5A 0.96300 0.57590 0.82450 0.0480 Uiso calc R 1.000
H H6A 1.13540 0.57160 0.68620 0.0490 Uiso calc R 1.000
H H11W 0.662(4) 0.407(3) 1.127(3) 0.069(9) Uiso . . 1.000
H H12W 0.719(4) 0.441(3) 1.031(3) 0.062(9) Uiso . . 1.000
H H21W 0.460(5) 0.730(4) 0.745(4) 0.060(10) Uiso . . 0.500
H H22W 0.515(5) 0.860(3) 0.755(3) 0.065(10) Uiso . . 0.500
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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O43A S4A C4A . . . 105.78(9) no
O41A S4A C4A . . . 106.12(9) no
O41A S4A O42A . . . 112.56(9) no
O41A S4A O43A . . . 113.37(10) no
O42A S4A O43A . . . 112.51(10) no
O42A S4A C4A . . . 105.74(9) no
H11W O1W H12W . . . 104(3) no
H21W O2W H22W . . . 97(4) no
C2 N1 C6 . . . 123.13(19) no
O21 N21 O22 . . . 123.47(19) no
O22 N21 C21 . . . 118.33(17) no
O21 N21 C21 . . . 118.17(17) no
O42 N41 C41 . . . 118.02(17) no
O41 N41 O42 . . . 123.59(19) no
O41 N41 C41 . . . 118.38(18) no
C6 N1 H1 . . . 117.1(16) no
C2 N1 H1 . . . 119.8(16) no
N1 C2 C3 . . . 118.39(18) no
N1 C2 C71 . . . 114.88(18) no
C3 C2 C71 . . . 126.73(18) no
C2 C3 C4 . . . 119.4(2) no
C3 C4 C5 . . . 120.3(2) no
C4 C5 C6 . . . 118.71(19) no
N1 C6 C5 . . . 120.0(2) no
C61 C11 C71 . . . 118.98(18) no
C21 C11 C71 . . . 124.29(18) no
C21 C11 C61 . . . 116.55(17) no
C11 C21 C31 . . . 123.34(17) no
N21 C21 C11 . . . 120.82(16) no
N21 C21 C31 . . . 115.84(16) no
C21 C31 C41 . . . 117.06(17) no
N41 C41 C51 . . . 119.43(17) no
C31 C41 C51 . . . 122.50(17) no
N41 C41 C31 . . . 118.07(17) no
C41 C51 C61 . . . 118.54(17) no
C11 C61 C51 . . . 121.97(18) no
C2 C71 C11 . . . 115.69(17) no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C6 C5 H5 . . . 121.00 no
C4 C5 H5 . . . 121.00 no
N1 C6 H6 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
C41 C31 H31 . . . 121.00 no
C21 C31 H31 . . . 121.00 no
C61 C51 H51 . . . 121.00 no
C41 C51 H51 . . . 121.00 no
C11 C61 H61 . . . 119.00 no
C51 C61 H61 . . . 119.00 no
H71 C71 H72 . . . 107.00 no
C2 C71 H72 . . . 108.00 no
C11 C71 H71 . . . 108.00 no
C11 C71 H72 . . . 108.00 no
C2 C71 H71 . . . 108.00 no
C1A C1A C2A 2_766 . . 121.47(17) no
C1A C1A C6A 2_766 . . 121.02(18) no
C2A C1A C6A . . . 117.51(19) no
C1A C2A C3A . . . 121.5(2) no
C2A C3A C4A . . . 119.8(2) no
S4A C4A C5A . . . 120.50(15) no
C3A C4A C5A . . . 119.8(2) no
S4A C4A C3A . . . 119.64(17) no
C4A C5A C6A . . . 120.1(2) no
C1A C6A C5A . . . 121.4(2) no
C1A C2A H2A . . . 119.00 no
C3A C2A H2A . . . 119.00 no
C4A C3A H3A . . . 120.00 no
C2A C3A H3A . . . 120.00 no
C4A C5A H5A . . . 120.00 no
C6A C5A H5A . . . 120.00 no
C1A C6A H6A . . . 119.00 no
C5A C6A H6A . . . 119.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S4A O42A . . 1.4479(16) no
S4A O43A . . 1.4558(19) no
S4A C4A . . 1.7687(19) no
S4A O41A . . 1.4481(15) no
O21 N21 . . 1.214(2) no
O22 N21 . . 1.224(2) no
O41 N41 . . 1.213(2) no
O42 N41 . . 1.210(3) no
O1W H11W . . 0.88(4) no
O1W H12W . . 0.80(3) no
O2W H21W . . 0.82(4) no
O2W H22W . . 0.87(3) no
N1 C6 . . 1.342(3) no
N1 C2 . . 1.348(2) no
N21 C21 . . 1.471(3) no
N41 C41 . . 1.479(3) no
N1 H1 . . 0.95(3) no
C2 C3 . . 1.375(3) no
C2 C71 . . 1.506(3) no
C3 C4 . . 1.392(3) no
C4 C5 . . 1.378(3) no
C5 C6 . . 1.365(3) no
C11 C61 . . 1.394(3) no
C11 C71 . . 1.512(3) no
C11 C21 . . 1.396(3) no
C21 C31 . . 1.381(3) no
C31 C41 . . 1.382(3) no
C41 C51 . . 1.378(3) no
C51 C61 . . 1.381(3) no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C31 H31 . . 0.9300 no
C51 H51 . . 0.9300 no
C61 H61 . . 0.9300 no
C71 H71 . . 0.9700 no
C71 H72 . . 0.9700 no
C1A C2A . . 1.381(3) no
C1A C6A . . 1.378(3) no
C1A C1A . 2_766 1.491(3) no
C2A C3A . . 1.387(4) no
C3A C4A . . 1.371(3) no
C4A C5A . . 1.367(3) no
C5A C6A . . 1.387(3) no
C2A H2A . . 0.9300 no
C3A H3A . . 0.9300 no
C5A H5A . . 0.9300 no
C6A H6A . . 0.9300 no
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
N1 H1 O1W . 0.95(3) 1.71(3) 2.655(3) 175(3) yes
O1W H11W O43A 2_667 0.88(4) 1.84(4) 2.716(2) 175(3) yes
O1W H12W O41A . 0.80(3) 2.01(3) 2.806(2) 172(3) yes
O2W H21W O43A . 0.82(4) 1.99(4) 2.761(4) 155(4) yes
O2W H22W O21 1_565 0.87(3) 2.32(3) 2.867(2) 124(3) yes
C2A H2A O2W 2_666 0.93 2.46 3.195(4) 136 no
C4 H4 O41A 1_545 0.93 2.40 3.309(3) 165 no
C5 H5 O42A 2_657 0.93 2.53 3.427(3) 163 no
C5A H5A O41A . 0.93 2.52 2.897(3) 105 no
C5A H5A O1W 2_767 0.93 2.58 3.232(3) 128 no
C6 H6 O2W 2_667 0.93 2.44 3.316(4) 156 no
C6 H6 O21 2_657 0.93 2.60 3.265(3) 129 no
C71 H72 O21 . 0.97 2.46 2.799(3) 100 no
C71 H72 O42A . 0.97 2.59 3.558(3) 176 no
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
O43A S4A C4A C5A . . . . 137.52(17) no
O42A S4A C4A C3A . . . . 73.2(2) no
O41A S4A C4A C3A . . . . -167.09(19) no
O41A S4A C4A C5A . . . . 16.81(19) no
O42A S4A C4A C5A . . . . -102.95(18) no
O43A S4A C4A C3A . . . . -46.4(2) no
C6 N1 C2 C71 . . . . -179.2(2) no
C6 N1 C2 C3 . . . . 0.2(3) no
C2 N1 C6 C5 . . . . -0.7(3) no
O21 N21 C21 C11 . . . . -32.8(3) no
O21 N21 C21 C31 . . . . 146.90(19) no
O22 N21 C21 C31 . . . . -31.1(3) no
O22 N21 C21 C11 . . . . 149.17(19) no
O42 N41 C41 C31 . . . . 178.02(19) no
O42 N41 C41 C51 . . . . -1.7(3) no
O41 N41 C41 C51 . . . . 176.96(19) no
O41 N41 C41 C31 . . . . -3.3(3) no
N1 C2 C71 C11 . . . . -173.63(18) no
N1 C2 C3 C4 . . . . 0.4(3) no
C71 C2 C3 C4 . . . . 179.8(2) no
C3 C2 C71 C11 . . . . 7.0(3) no
C2 C3 C4 C5 . . . . -0.6(4) no
C3 C4 C5 C6 . . . . 0.1(4) no
C4 C5 C6 N1 . . . . 0.5(4) no
C21 C11 C71 C2 . . . . 88.6(2) no
C61 C11 C71 C2 . . . . -96.6(2) no
C61 C11 C21 N21 . . . . 178.55(17) no
C61 C11 C21 C31 . . . . -1.2(3) no
C71 C11 C21 N21 . . . . -6.5(3) no
C71 C11 C21 C31 . . . . 173.82(18) no
C21 C11 C61 C51 . . . . -1.0(3) no
C71 C11 C61 C51 . . . . -176.22(18) no
N21 C21 C31 C41 . . . . -177.51(17) no
C11 C21 C31 C41 . . . . 2.2(3) no
C21 C31 C41 N41 . . . . 179.06(17) no
C21 C31 C41 C51 . . . . -1.2(3) no
C31 C41 C51 C61 . . . . -0.8(3) no
N41 C41 C51 C61 . . . . 178.96(18) no
C41 C51 C61 C11 . . . . 1.9(3) no
C6A C1A C2A C3A . . . . -1.1(4) no
C1A C1A C2A C3A 2_766 . . . 178.3(2) no
C2A C1A C6A C5A . . . . 0.7(3) no
C1A C1A C6A C5A 2_766 . . . -178.72(19) no
C2A C1A C1A C2A . . 2_766 2_766 -180.0(2) no
C2A C1A C1A C6A . . 2_766 2_766 0.7(3) no
C6A C1A C1A C2A . . 2_766 2_766 -0.7(3) no
C6A C1A C1A C6A . . 2_766 2_766 180.0(2) no
C1A C2A C3A C4A . . . . 0.6(4) no
C2A C3A C4A S4A . . . . -175.7(2) no
C2A C3A C4A C5A . . . . 0.4(4) no
S4A C4A C5A C6A . . . . 175.26(16) no
C3A C4A C5A C6A . . . . -0.8(3) no
C4A C5A C6A C1A . . . . 0.3(3) no
