#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013210.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_2013210
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o98
_journal_page_last  o101
_publ_section_title
;
A chain of edge-fused rings generated by the combination of an N---H...O
hydrogen bond and an iodo--nitro interaction in
2-iodobenzaldehyde 4-nitrophenylhydrazone versus disordered and effectively
isolated molecules in 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone
;
loop_
_publ_author_name
  'Glidewell, Christopher'
  'Low, John N.'
  'Skakle, Janet M. S.'
  'Wardell, James L.'
_chemical_formula_moiety  'C13 H9 I N4 O4'
_chemical_formula_sum  'C13 H9 I N4 O4'
_chemical_formula_iupac  'C13 H9 I N4 O4'
_chemical_formula_weight  412.14
_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  7.8890(5)
_cell_length_b  8.1405(6)
_cell_length_c  12.1760(10)
_cell_angle_alpha  83.876(4)
_cell_angle_beta  83.679(4)
_cell_angle_gamma  63.151(3)
_cell_volume  691.98(9)
_cell_formula_units_Z  2
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.978
_diffrn_ambient_temperature  120(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
  I22 0.53164(6) 0.06529(5) 0.14789(3) 0.0433(2) Uani d . 1 . . I
  C11 0.292(2) 0.375(2) 0.6377(12) 0.035(4) Uani d P 0.681(5) A -1 C
  C12 0.1102(18) 0.4286(18) 0.6936(10) 0.023(2) Uani d P 0.681(5) A -1 C
  C13 0.0548(19) 0.511(2) 0.7893(12) 0.033(3) Uani d P 0.681(5) A -1 C
  C14 0.178(2) 0.547(2) 0.8405(10) 0.028(3) Uani d P 0.681(5) A -1 C
  N14 0.121(3) 0.636(2) 0.9453(11) 0.038(3) Uani d P 0.681(5) A -1 N
  O41 -0.0497(15) 0.700(2) 0.9755(14) 0.048(4) Uani d P 0.681(5) A -1 O
  O42 0.2389(15) 0.6504(14) 0.9943(8) 0.064(3) Uani d P 0.681(5) A -1 O
  C15 0.3615(18) 0.5001(16) 0.7941(10) 0.033(3) Uani d P 0.681(5) A -1 C
  C16 0.4195(17) 0.4165(16) 0.6933(9) 0.023(2) Uani d P 0.681(5) A -1 C
  N12 -0.0359(11) 0.4134(10) 0.6527(6) 0.0397(18) Uani d P 0.681(5) A -1 N
  O121 -0.0011(10) 0.3349(8) 0.5662(5) 0.0441(16) Uani d P 0.681(5) A -1 O
  O122 -0.1960(11) 0.4781(11) 0.7002(7) 0.064(2) Uani d P 0.681(5) A -1 O
  C21 0.7318(13) 0.1108(11) 0.3385(7) 0.035(2) Uani d P 0.681(5) A -1 C
  C22 0.7557(13) 0.0478(10) 0.2313(7) 0.036(2) Uani d P 0.681(5) A -1 C
  C23 0.9306(14) -0.0210(12) 0.1744(8) 0.040(2) Uani d P 0.681(5) A -1 C
  C24 1.086(3) -0.033(2) 0.2216(14) 0.041(2) Uani d P 0.681(5) A -1 C
  C25 1.0691(18) 0.0367(12) 0.3246(8) 0.041(2) Uani d P 0.681(5) A -1 C
  C26 0.8912(14) 0.1087(12) 0.3821(8) 0.045(2) Uani d P 0.681(5) A -1 C
  C27 0.5497(14) 0.1763(10) 0.4046(8) 0.0410(15) Uani d P 0.681(5) A -1 C
  N2 0.5290(11) 0.2364(9) 0.4988(6) 0.0410(15) Uani d P 0.681(5) A -1 N
  N1 0.3590(8) 0.2881(7) 0.5470(4) 0.0373(12) Uani d . 1 . . N
  C911 0.322(3) 0.364(4) 0.6535(17) 0.017(8) Uiso d PG 0.319(5) A -2 C
  C912 0.456(2) 0.386(3) 0.7081(14) 0.025(7) Uiso d PG 0.319(5) A -2 C
  C913 0.403(2) 0.468(3) 0.8086(14) 0.014(5) Uiso d PG 0.319(5) A -2 C
  C914 0.217(3) 0.529(4) 0.8545(16) 0.015(8) Uiso d PGD 0.319(5) A -2 C
  C915 0.084(2) 0.507(4) 0.7999(19) 0.025(7) Uiso d PG 0.319(5) A -2 C
  C916 0.136(3) 0.424(4) 0.699(2) 0.034(9) Uiso d PG 0.319(5) A -2 C
  N912 0.6091(18) 0.4068(16) 0.6531(10) 0.021(3) Uiso d P 0.319(5) A -2 N
  O921 0.6751(16) 0.3353(15) 0.5614(9) 0.028(3) Uiso d P 0.319(5) A -2 O
  O922 0.6951(18) 0.4628(14) 0.7071(9) 0.024(3) Uiso d P 0.319(5) A -2 O
  N92 0.260(2) 0.2378(18) 0.4910(12) 0.028(3) Uiso d P 0.319(5) A -2 N
  C927 0.338(2) 0.167(2) 0.3986(13) 0.027(4) Uiso d P 0.319(5) A -2 C
  C921 0.235(2) 0.102(2) 0.3353(13) 0.023(3) Uiso d P 0.319(5) A -2 C
  C922 0.307(3) 0.039(2) 0.2290(14) 0.031(4) Uiso d P 0.319(5) A -2 C
  C923 0.214(2) -0.036(2) 0.1712(13) 0.023(3) Uiso d P 0.319(5) A -2 C
  C924 0.049(5) -0.038(5) 0.215(3) 0.026(6) Uiso d P 0.319(5) A -2 C
  C925 -0.022(3) 0.028(2) 0.3234(16) 0.023(4) Uiso d P 0.319(5) A -2 C
  C926 0.064(2) 0.102(2) 0.3799(15) 0.024(3) Uiso d P 0.319(5) A -2 C
  N914 0.168(3) 0.617(6) 0.956(2) 0.033(10) Uiso d PD 0.319(5) A -2 N
  O941 -0.002(5) 0.689(6) 0.990(4) 0.036(4) Uiso d PD 0.319(5) A -2 O
  O942 0.291(3) 0.616(3) 1.0139(16) 0.036(4) Uiso d PD 0.319(5) A -2 O
  H13 -0.0708 0.5449 0.8215 0.040 Uiso calc PR 0.681(5) A -1 H
  H15 0.4472 0.5247 0.8307 0.040 Uiso calc PR 0.681(5) A -1 H
  H16 0.5444 0.3863 0.6610 0.028 Uiso calc PR 0.681(5) A -1 H
  H23 0.9444 -0.0603 0.1019 0.048 Uiso calc PR 0.681(5) A -1 H
  H24 1.2077 -0.0905 0.1836 0.049 Uiso calc PR 0.681(5) A -1 H
  H25 1.1765 0.0349 0.3543 0.049 Uiso calc PR 0.681(5) A -1 H
  H26 0.8767 0.1574 0.4519 0.054 Uiso calc PR 0.681(5) A -1 H
  H27 0.4441 0.1734 0.3756 0.049 Uiso calc PR 0.681(5) A -1 H
  H1 0.2805 0.2614 0.5151 0.045 Uiso calc PR 0.681(5) A -1 H
  H91 0.4691 0.2727 0.5131 0.045 Uiso calc PR 0.319(5) A -2 H
  H913 0.4945 0.4829 0.8459 0.017 Uiso d PG 0.319(5) A -2 H
  H915 -0.0433 0.5482 0.8313 0.030 Uiso d PG 0.319(5) A -2 H
  H916 0.0448 0.4094 0.6621 0.041 Uiso d PG 0.319(5) A -2 H
  H927 0.4601 0.1566 0.3719 0.032 Uiso calc PR 0.319(5) A -2 H
  H923 0.2676 -0.0849 0.1013 0.027 Uiso calc PR 0.319(5) A -2 H
  H924 -0.0172 -0.0829 0.1756 0.032 Uiso calc PR 0.319(5) A -2 H
  H925 -0.1336 0.0213 0.3566 0.027 Uiso calc PR 0.319(5) A -2 H
  H926 0.0087 0.1520 0.4492 0.029 Uiso calc PR 0.319(5) A -2 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
  I22 0.0573(3) 0.0536(3) 0.0348(3) -0.0392(2) 0.0088(2) -0.01212(19)
  C11 0.038(7) 0.030(6) 0.034(6) -0.014(5) -0.015(6) 0.010(5)
  C12 0.017(4) 0.020(4) 0.032(4) -0.008(3) 0.002(3) -0.004(3)
  C13 0.025(4) 0.031(4) 0.044(5) -0.016(3) -0.004(4) 0.009(3)
  C14 0.044(7) 0.022(6) 0.016(5) -0.015(5) 0.008(5) -0.007(4)
  N14 0.044(7) 0.026(6) 0.030(5) -0.007(6) 0.014(6) -0.005(5)
  O41 0.045(8) 0.030(4) 0.052(8) -0.010(6) 0.031(7) -0.003(5)
  O42 0.058(7) 0.072(7) 0.044(5) -0.004(5) -0.029(5) -0.021(4)
  C15 0.025(4) 0.031(4) 0.044(5) -0.016(3) -0.004(4) 0.009(3)
  C16 0.017(4) 0.020(4) 0.032(4) -0.008(3) 0.002(3) -0.004(3)
  N12 0.040(5) 0.036(4) 0.037(4) -0.009(3) -0.011(4) -0.006(3)
  O121 0.060(4) 0.043(3) 0.033(3) -0.025(3) -0.008(3) -0.003(3)
  O122 0.033(4) 0.071(5) 0.077(6) -0.005(4) -0.009(4) -0.042(4)
  C21 0.041(5) 0.027(4) 0.026(4) -0.008(4) 0.004(4) 0.000(3)
  C22 0.060(6) 0.020(4) 0.024(4) -0.015(4) 0.003(4) -0.002(3)
  C23 0.050(6) 0.039(5) 0.032(5) -0.024(4) 0.009(4) 0.001(4)
  C24 0.054(6) 0.031(4) 0.031(4) -0.012(4) 0.007(4) -0.008(3)
  C25 0.054(6) 0.031(4) 0.031(4) -0.012(4) 0.007(4) -0.008(3)
  C26 0.048(6) 0.036(5) 0.035(5) -0.006(4) 0.001(5) 0.002(4)
  C27 0.047(4) 0.018(2) 0.036(3) 0.002(2) 0.015(3) -0.005(2)
  N2 0.047(4) 0.018(2) 0.036(3) 0.002(2) 0.015(3) -0.005(2)
  N1 0.048(3) 0.035(2) 0.026(2) -0.015(2) 0.000(2) -0.007(2)
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
  I22 C922 . 2.019(17) no
  I22 C22 . 2.077(10) no
  C11 N1 . 1.306(14) no
  C11 C12 . 1.414(13) no
  C11 C16 . 1.441(18) no
  C12 C13 . 1.339(13) no
  C12 N12 . 1.364(14) no
  C12 H916 . 0.7519 no
  C13 C14 . 1.358(18) no
  C13 H13 . 0.95 no
  C13 H915 . 0.8288 no
  C14 C15 . 1.389(15) no
  C14 N14 . 1.460(12) no
  N14 O42 . 1.214(17) no
  N14 O41 . 1.23(2) no
  C15 C16 . 1.398(12) no
  C15 H15 . 0.95 no
  C15 H913 . 1.2302 no
  C16 H16 . 0.95 no
  N12 O122 . 1.228(11) no
  N12 O121 . 1.231(9) no
  N12 H916 . 0.6459 no
  C21 C26 . 1.410(14) no
  C21 C22 . 1.416(12) no
  C21 C27 . 1.463(12) no
  C22 C23 . 1.368(13) no
  C23 C24 . 1.37(2) no
  C23 H23 . 0.95 no
  C24 C25 . 1.40(2) no
  C24 H24 . 0.95 no
  C25 C26 . 1.390(15) no
  C25 H25 . 0.95 no
  C26 H26 . 0.95 no
  C27 N2 . 1.261(12) no
  C27 H27 . 0.95 no
  N2 N1 . 1.300(9) no
  N1 N92 . 1.309(15) no
  N1 C911 . 1.440(17) no
  N1 H1 . 0.88 no
  N1 H91 . 0.88 no
  C911 C912 . 1.39 no
  C911 C916 . 1.39 no
  C912 N912 . 1.39(2) no
  C912 C913 . 1.39 no
  C913 C914 . 1.39 no
  C913 H913 . 0.95 no
  C914 C915 . 1.39 no
  C914 N914 . 1.42(5) no
  C915 C916 . 1.39 no
  C915 H915 . 0.95 no
  C916 H916 . 0.95 no
  N912 O922 . 1.242(17) no
  N912 O921 . 1.261(17) no
  N92 C927 . 1.28(2) no
  C927 C921 . 1.46(2) no
  C927 H927 . 0.95 no
  C921 C926 . 1.40(2) no
  C921 C922 . 1.41(2) no
  C922 C923 . 1.42(2) no
  C923 C924 . 1.36(3) no
  C923 H923 . 0.95 no
  C924 C925 . 1.43(4) no
  C924 H924 . 0.95 no
  C925 C926 . 1.36(2) no
  C925 H925 . 0.95 no
  C926 H926 . 0.95 no
  N914 O941 . 1.24(4) no
  N914 O942 . 1.26(4) no