#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012976.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_2012976
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o632
_journal_page_last  o634
_publ_section_title
;
A zwitterionic viologen disulfonate-hydroquinone charge-transfer crystal:
4,4'-bipyridinium-1,1'-bis(2-ethylsulfonate)-bis(hydroquinone)
;
loop_
_publ_author_name
  'Robinson, Paul D.'
  'Smith, Kevin R.'
  'Vermeulen, Lori A.'
_chemical_formula_moiety  'C14 H16 N2 O6 S2 , 2C6 H6 O2'
_chemical_formula_sum  'C26 H28 N2 O10 S2'
_chemical_formula_weight  592.62
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  20.006(5)
_cell_length_b  11.072(3)
_cell_length_c  11.882(3)
_cell_angle_alpha  90
_cell_angle_beta  98.94(2)
_cell_angle_gamma  90
_cell_volume  2600.2(12)
_cell_formula_units_Z  4
_cell_measurement_temperature  296
_exptl_crystal_density_diffrn  1.514
_diffrn_ambient_temperature  296
loop_
_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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  S1 0.25200(3) 0.02858(6) 0.42643(5) 0.03072(18) Uani d . 1 . . S
  O1 0.21681(9) 0.11056(17) 0.49050(16) 0.0501(5) Uani d . 1 . . O
  O2 0.32480(8) 0.03458(19) 0.45762(14) 0.0481(5) Uani d . 1 . . O
  O3 0.22605(9) -0.09374(16) 0.42906(15) 0.0461(5) Uani d . 1 . . O
  O4 0.36208(9) 0.1026(2) 0.68028(17) 0.0602(6) Uani d . 1 . . O
  O5 0.12228(9) -0.11767(19) 0.55739(15) 0.0496(5) Uani d . 1 . . O
  N1 0.32662(9) 0.21765(17) 0.25711(15) 0.0287(4) Uani d . 1 . . N
  C1 0.36850(12) 0.2564(2) 0.3489(2) 0.0345(6) Uani d . 1 . . C
  C2 0.43663(12) 0.2626(2) 0.3474(2) 0.0344(6) Uani d . 1 . . C
  C3 0.46307(11) 0.2291(2) 0.25100(19) 0.0281(5) Uani d . 1 . . C
  C4 0.41782(11) 0.1931(2) 0.15581(19) 0.0318(5) Uani d . 1 . . C
  C5 0.35010(12) 0.1877(2) 0.16095(19) 0.0334(6) Uani d . 1 . . C
  C6 0.25297(11) 0.2045(2) 0.2613(2) 0.0383(6) Uani d . 1 . . C
  C7 0.23396(12) 0.0744(2) 0.28158(19) 0.0357(6) Uani d . 1 . . C
  C8 0.43086(12) 0.1018(2) 0.7124(2) 0.0388(6) Uani d . 1 . . C
  C9 0.45540(13) 0.1002(3) 0.8273(2) 0.0498(7) Uani d . 1 . . C
  H9 0.4255 0.0990 0.8799 0.060 Uiso calc R 1 . . H
  C10 0.47568(14) 0.1004(3) 0.6352(2) 0.0483(7) Uani d . 1 . . C
  C11 0.01358(12) -0.0703(2) 0.5965(2) 0.0393(6) Uani d . 1 . . C
  C12 0.06279(12) -0.0573(2) 0.52679(19) 0.0361(6) Uani d . 1 . . C
  C13 0.04836(12) 0.0135(2) 0.4303(2) 0.0391(6) Uani d . 1 . . C
  H1 0.3512 0.2792 0.4140 0.041 Uiso calc R 1 . . H
  H2 0.4654 0.2894 0.4116 0.041 Uiso calc R 1 . . H
  H4 0.3530 0.0894 0.6117 0.090 Uiso calc R 1 . . H
  H5 0.1487 -0.0997 0.5137 0.074 Uiso calc R 1 . . H
  H4A 0.4337 0.1728 0.0888 0.038 Uiso calc R 1 . . H
  H5A 0.3201 0.1631 0.0974 0.040 Uiso calc R 1 . . H
  H6A 0.2274 0.2323 0.1899 0.046 Uiso calc R 1 . . H
  H6B 0.2409 0.2548 0.3219 0.046 Uiso calc R 1 . . H
  H7A 0.2582 0.0219 0.2364 0.043 Uiso calc R 1 . . H
  H7B 0.1860 0.0640 0.2551 0.043 Uiso calc R 1 . . H
  H10 0.4594 0.0995 0.5575 0.058 Uiso calc R 1 . . H
  H11 0.0224 -0.1176 0.6618 0.047 Uiso calc R 1 . . H
  H13 0.0808 0.0231 0.3828 0.047 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  S1 0.0286(3) 0.0349(3) 0.0290(3) -0.0044(3) 0.0053(2) -0.0020(3)
  O1 0.0548(12) 0.0504(12) 0.0493(11) 0.0010(9) 0.0210(9) -0.0120(9)
  O2 0.0289(9) 0.0732(14) 0.0404(10) -0.0026(9) 0.0002(7) 0.0090(9)
  O3 0.0600(12) 0.0339(10) 0.0460(11) -0.0116(9) 0.0136(9) -0.0013(8)
  O4 0.0353(10) 0.0908(17) 0.0508(12) 0.0040(11) -0.0042(8) -0.0136(12)
  O5 0.0353(10) 0.0697(14) 0.0440(11) -0.0023(10) 0.0073(8) 0.0058(10)
  N1 0.0254(10) 0.0261(10) 0.0353(11) 0.0005(8) 0.0067(8) 0.0017(8)
  C1 0.0359(13) 0.0346(14) 0.0355(13) -0.0053(11) 0.0131(11) -0.0089(11)
  C2 0.0311(12) 0.0393(14) 0.0332(13) -0.0063(11) 0.0060(10) -0.0099(11)
  C3 0.0292(12) 0.0247(12) 0.0309(12) -0.0006(10) 0.0068(9) 0.0008(10)
  C4 0.0308(13) 0.0370(14) 0.0289(12) 0.0027(10) 0.0091(10) -0.0002(10)
  C5 0.0359(14) 0.0341(14) 0.0292(12) -0.0018(11) 0.0023(10) -0.0004(11)
  C6 0.0227(11) 0.0456(17) 0.0471(15) 0.0024(11) 0.0069(10) 0.0093(12)
  C7 0.0289(12) 0.0465(15) 0.0305(12) -0.0085(11) 0.0012(9) 0.0030(11)
  C8 0.0303(13) 0.0401(15) 0.0437(14) 0.0012(11) -0.0014(11) -0.0043(12)
  C9 0.0389(15) 0.068(2) 0.0430(15) 0.0046(14) 0.0074(12) -0.0158(14)
  C10 0.0418(15) 0.0623(19) 0.0379(14) -0.0046(14) -0.0034(11) 0.0123(13)
  C11 0.0417(15) 0.0487(16) 0.0274(12) -0.0116(12) 0.0053(10) 0.0004(11)
  C12 0.0318(13) 0.0462(16) 0.0298(12) -0.0087(11) 0.0038(10) -0.0062(11)
  C13 0.0348(14) 0.0537(16) 0.0308(13) -0.0123(12) 0.0115(10) -0.0045(12)
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
  S1 O1 . 1.4373(18) no
  S1 O2 . 1.4476(17) no
  S1 O3 . 1.4525(18) no
  S1 C7 . 1.777(2) no
  C6 C7 . 1.518(3) no
  N1 C6 . 1.489(3) no
  N1 C1 . 1.338(3) no
  C1 C2 . 1.367(3) no
  C2 C3 . 1.385(3) no
  C3 C4 . 1.393(3) no
  C4 C5 . 1.367(3) no
  N1 C5 . 1.343(3) no
  C3 C3 2_655 1.481(4) no
  O4 C8 . 1.370(3) no
  C8 C9 . 1.377(4) no
  C8 C10 . 1.379(4) no
  C9 C10 2_656 1.382(4) no
  O5 C12 . 1.364(3) no
  C11 C12 . 1.389(3) no
  C12 C13 . 1.381(3) no
  C11 C13 5_556 1.382(4) no
  O5 H5 . 0.8200 no
  O4 H4 . 0.8200 no
  C1 H1 . 0.9300 no
  C2 H2 . 0.9300 no
  C4 H4A . 0.9300 no
  C5 H5A . 0.9300 no
  C6 H6A . 0.9700 no
  C6 H6B . 0.9700 no
  C7 H7A . 0.9700 no
  C7 H7B . 0.9700 no
  C9 H9 . 0.9300 no
  C10 H10 . 0.9300 no
  C11 H11 . 0.9300 no
  C13 H13 . 0.9300 no