#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202602.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_2202602
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o917
_journal_page_last  o918
_publ_section_title
;
N-Methyl-N'-(3-phthalimidopropyl)-4,4'-bipyridinium diiodide
;
loop_
_publ_author_name
  'Sakai*, Ken'
  'Okamoto, Ken'
  'Takahashi, Satoru'
  'Yokokawa, Kazuo'
_chemical_formula_moiety  'C22 H21 N3 O2 2+, 2I 1-'
_chemical_formula_sum  'C22 H21 I2 N3 O2'
_chemical_formula_iupac  'C22 H21 N3 O2 2+, 2I 1-'
_chemical_formula_weight  613.22
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  6.0535(5)
_cell_length_b  7.4674(6)
_cell_length_c  25.776(2)
_cell_angle_alpha  83.7150(10)
_cell_angle_beta  88.570(2)
_cell_angle_gamma  82.2230(10)
_cell_volume  1147.45(16)
_cell_formula_units_Z  2
_cell_measurement_temperature  296(2)
_exptl_crystal_density_diffrn  1.775
_diffrn_ambient_temperature  296(2)
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
  I1 0.19500(5) 0.72933(4) 0.254201(15) 0.06628(13) Uani d . 1 . . I
  I2 0.84565(5) 0.74396(4) 0.065322(12) 0.05327(11) Uani d . 1 . . I
  O1 0.4876(5) 0.2479(5) 0.44316(13) 0.0672(9) Uani d . 1 . . O
  O2 -0.1257(6) 0.3202(5) 0.34073(14) 0.0749(10) Uani d . 1 . . O
  N1 0.1978(6) 0.2446(5) 0.38681(13) 0.0492(8) Uani d . 1 . . N
  N2 0.5727(5) 0.2105(4) 0.24093(12) 0.0377(7) Uani d . 1 . . N
  N3 1.4807(5) 0.2657(4) 0.06983(12) 0.0398(7) Uani d . 1 . . N
  C1 0.3138(7) 0.3200(6) 0.42332(16) 0.0499(10) Uani d . 1 . . C
  C2 0.1766(7) 0.4947(6) 0.43191(16) 0.0489(10) Uani d . 1 . . C
  C3 0.2117(8) 0.6203(6) 0.46498(18) 0.0586(11) Uani d . 1 . . C
  H3 0.3390 0.6064 0.4853 0.070 Uiso calc R 1 . . H
  C4 0.0484(10) 0.7685(7) 0.4666(2) 0.0697(14) Uani d . 1 . . C
  H4 0.0648 0.8558 0.4889 0.084 Uiso calc R 1 . . H
  C5 -0.1378(10) 0.7887(8) 0.4359(2) 0.0776(16) Uani d . 1 . . C
  H5 -0.2434 0.8909 0.4373 0.093 Uiso calc R 1 . . H
  C6 -0.1721(9) 0.6599(8) 0.4028(2) 0.0715(14) Uani d . 1 . . C
  H6 -0.2990 0.6727 0.3824 0.086 Uiso calc R 1 . . H
  C7 -0.0104(7) 0.5141(6) 0.40176(17) 0.0527(10) Uani d . 1 . . C
  C8 0.0021(7) 0.3550(7) 0.37156(17) 0.0552(11) Uani d . 1 . . C
  C9 0.2768(8) 0.0703(6) 0.36789(16) 0.0530(11) Uani d . 1 . . C
  H9A 0.1530 0.0257 0.3525 0.064 Uiso calc R 1 . . H
  H9B 0.3287 -0.0163 0.3973 0.064 Uiso calc R 1 . . H
  C10 0.4626(7) 0.0793(5) 0.32801(15) 0.0465(9) Uani d . 1 . . C
  H10A 0.5837 0.1301 0.3425 0.056 Uiso calc R 1 . . H
  H10B 0.5191 -0.0427 0.3201 0.056 Uiso calc R 1 . . H
  C11 0.3849(6) 0.1939(5) 0.27838(15) 0.0434(9) Uani d . 1 . . C
  H11A 0.2703 0.1391 0.2626 0.052 Uiso calc R 1 . . H
  H11B 0.3203 0.3139 0.2864 0.052 Uiso calc R 1 . . H
  C12 0.6752(7) 0.3591(5) 0.23621(15) 0.0433(9) Uani d . 1 . . C
  H12 0.6250 0.4538 0.2560 0.052 Uiso calc R 1 . . H
  C13 0.8524(6) 0.3747(5) 0.20284(16) 0.0420(9) Uani d . 1 . . C
  H13 0.9205 0.4798 0.1997 0.050 Uiso calc R 1 . . H
  C14 0.9306(6) 0.2327(5) 0.17358(14) 0.0345(7) Uani d . 1 . . C
  C15 0.8192(6) 0.0811(5) 0.17903(15) 0.0420(9) Uani d . 1 . . C
  H15 0.8659 -0.0154 0.1597 0.050 Uiso calc R 1 . . H
  C16 0.6415(7) 0.0722(5) 0.21254(16) 0.0453(9) Uani d . 1 . . C
  H16 0.5679 -0.0300 0.2157 0.054 Uiso calc R 1 . . H
  C17 1.3702(7) 0.1209(6) 0.07274(17) 0.0503(10) Uani d . 1 . . C
  H17 1.4133 0.0294 0.0514 0.060 Uiso calc R 1 . . H
  C18 1.1957(7) 0.1061(5) 0.10658(17) 0.0478(10) Uani d . 1 . . C
  H18 1.1224 0.0037 0.1086 0.057 Uiso calc R 1 . . H
  C19 1.1264(6) 0.2432(5) 0.13816(14) 0.0361(8) Uani d . 1 . . C
  C20 1.2465(7) 0.3901(5) 0.13447(15) 0.0425(9) Uani d . 1 . . C
  H20 1.2072 0.4838 0.1553 0.051 Uiso calc R 1 . . H
  C21 1.4225(6) 0.3974(5) 0.10025(15) 0.0417(9) Uani d . 1 . . C
  H21 1.5025 0.4958 0.0983 0.050 Uiso calc R 1 . . H
  C22 1.6680(7) 0.2759(6) 0.03166(17) 0.0495(10) Uani d . 1 . . C
  H22A 1.6097 0.3005 -0.0031 0.074 Uiso calc R 1 . . H
  H22B 1.7645 0.1622 0.0347 0.074 Uiso calc R 1 . . H
  H22C 1.7506 0.3714 0.0387 0.074 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
  I1 0.0654(2) 0.03703(17) 0.1002(3) -0.01153(14) -0.01225(18) -0.01576(15)
  I2 0.05358(18) 0.03899(16) 0.0708(2) -0.01621(12) -0.00222(14) -0.00893(13)
  O1 0.062(2) 0.074(2) 0.066(2) 0.0056(17) -0.0165(17) -0.0240(17)
  O2 0.066(2) 0.090(3) 0.075(2) -0.0285(19) -0.0166(18) -0.0111(19)
  N1 0.052(2) 0.056(2) 0.0440(19) -0.0184(17) -0.0002(16) -0.0115(16)
  N2 0.0386(16) 0.0334(16) 0.0407(17) -0.0050(13) 0.0008(13) -0.0016(13)
  N3 0.0373(16) 0.0357(16) 0.0467(18) -0.0064(13) -0.0003(14) -0.0041(13)
  C1 0.054(2) 0.058(3) 0.041(2) -0.014(2) 0.0009(19) -0.0103(18)
  C2 0.053(2) 0.051(2) 0.043(2) -0.0112(19) 0.0062(19) -0.0053(18)
  C3 0.068(3) 0.054(3) 0.055(3) -0.009(2) 0.003(2) -0.010(2)
  C4 0.094(4) 0.051(3) 0.063(3) -0.009(3) 0.011(3) -0.007(2)
  C5 0.081(4) 0.064(3) 0.080(4) 0.006(3) 0.019(3) 0.004(3)
  C6 0.062(3) 0.081(4) 0.065(3) -0.003(3) -0.002(2) 0.011(3)
  C7 0.051(2) 0.057(3) 0.050(2) -0.011(2) 0.0036(19) 0.002(2)
  C8 0.052(3) 0.070(3) 0.047(2) -0.025(2) 0.000(2) -0.001(2)
  C9 0.068(3) 0.052(2) 0.044(2) -0.026(2) 0.001(2) -0.0043(18)
  C10 0.052(2) 0.041(2) 0.049(2) -0.0124(18) -0.0018(19) -0.0051(17)
  C11 0.043(2) 0.040(2) 0.048(2) -0.0071(17) 0.0019(17) -0.0038(16)
  C12 0.049(2) 0.037(2) 0.045(2) -0.0068(17) -0.0011(18) -0.0115(16)
  C13 0.042(2) 0.0325(18) 0.055(2) -0.0131(16) 0.0019(17) -0.0110(16)
  C14 0.0359(18) 0.0293(17) 0.0384(19) -0.0046(14) -0.0029(15) -0.0033(14)
  C15 0.046(2) 0.0301(18) 0.050(2) -0.0065(16) 0.0041(18) -0.0079(16)
  C16 0.054(2) 0.0302(18) 0.053(2) -0.0114(17) 0.0057(19) -0.0052(16)
  C17 0.047(2) 0.045(2) 0.065(3) -0.0169(18) 0.009(2) -0.0222(19)
  C18 0.049(2) 0.039(2) 0.062(3) -0.0173(18) 0.007(2) -0.0207(18)
  C19 0.0368(18) 0.0293(17) 0.042(2) -0.0052(14) -0.0060(15) -0.0023(14)
  C20 0.051(2) 0.0305(18) 0.048(2) -0.0105(16) 0.0002(18) -0.0067(15)
  C21 0.046(2) 0.0293(18) 0.051(2) -0.0118(16) -0.0008(18) -0.0027(16)
  C22 0.045(2) 0.048(2) 0.057(3) -0.0128(18) 0.0096(19) -0.0081(19)
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
  O1 C1 . 1.213(5) ?
  O2 C8 . 1.195(5) ?
  N1 C8 . 1.387(6) ?
  N1 C1 . 1.397(5) ?
  N1 C9 . 1.456(5) ?
  N2 C12 . 1.336(5) ?
  N2 C16 . 1.345(5) ?
  N2 C11 . 1.482(5) ?
  N3 C21 . 1.329(5) ?
  N3 C17 . 1.341(5) ?
  N3 C22 . 1.486(5) ?
  C1 C2 . 1.483(6) ?
  C2 C7 . 1.372(6) ?
  C2 C3 . 1.375(6) ?
  C3 C4 . 1.384(7) ?
  C3 H3 . 0.9300 ?
  C4 C5 . 1.375(8) ?
  C4 H4 . 0.9300 ?
  C5 C6 . 1.393(8) ?
  C5 H5 . 0.9300 ?
  C6 C7 . 1.364(7) ?
  C6 H6 . 0.9300 ?
  C7 C8 . 1.483(6) ?
  C9 C10 . 1.508(5) ?
  C9 H9A . 0.9700 ?
  C9 H9B . 0.9700 ?
  C10 C11 . 1.507(5) ?
  C10 H10A . 0.9700 ?
  C10 H10B . 0.9700 ?
  C11 H11A . 0.9700 ?
  C11 H11B . 0.9700 ?
  C12 C13 . 1.367(5) ?
  C12 H12 . 0.9300 ?
  C13 C14 . 1.392(5) ?
  C13 H13 . 0.9300 ?
  C14 C15 . 1.386(5) ?
  C14 C19 . 1.483(5) ?
  C15 C16 . 1.367(5) ?
  C15 H15 . 0.9300 ?
  C16 H16 . 0.9300 ?
  C17 C18 . 1.362(6) ?
  C17 H17 . 0.9300 ?
  C18 C19 . 1.392(5) ?
  C18 H18 . 0.9300 ?
  C19 C20 . 1.389(5) ?
  C20 C21 . 1.369(5) ?
  C20 H20 . 0.9300 ?
  C21 H21 . 0.9300 ?
  C22 H22A . 0.9600 ?
  C22 H22B . 0.9600 ?
  C22 H22C . 0.9600 ?