#------------------------------------------------------------------------------
#$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013209.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_2013209
_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 H10 I N3 O2'
_chemical_formula_sum  'C13 H10 I N3 O2'
_chemical_formula_iupac  'C13 H10 I N3 O2'
_chemical_formula_weight  367.14
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, z+1/2'
  'x+1/2, -y, z'
  '-x+1/2, y, z+1/2'
_cell_length_a  24.0858(11)
_cell_length_b  5.0699(2)
_cell_length_c  10.5080(4)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1283.16(9)
_cell_formula_units_Z  4
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.900
_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 0.876111(14) 0.80511(6) 0.99980(7) 0.02451(12) Uani d . 1 . . I
  O41 0.75761(18) -0.9173(10) 0.3440(4) 0.0298(10) Uani d . 1 . . O
  O42 0.8286(2) -0.7960(8) 0.2309(4) 0.0342(11) Uani d . 1 . . O
  N1 0.8383(2) 0.0228(9) 0.6790(5) 0.0238(12) Uani d . 1 . . N
  N2 0.88431(19) 0.1797(8) 0.6758(5) 0.0181(11) Uani d . 1 . . N
  N4 0.7976(2) -0.7716(10) 0.3259(5) 0.0252(12) Uani d . 1 . . N
  C11 0.8295(2) -0.1731(11) 0.5902(5) 0.0169(13) Uani d . 1 . . C
  C12 0.7819(3) -0.3277(11) 0.6028(6) 0.0203(14) Uani d . 1 . . C
  C13 0.7719(2) -0.5242(10) 0.5156(7) 0.0217(14) Uani d . 1 . . C
  C14 0.8089(2) -0.5666(12) 0.4170(5) 0.0190(12) Uani d . 1 . . C
  C15 0.8567(2) -0.4147(13) 0.4038(5) 0.0211(13) Uani d . 1 . . C
  C16 0.8674(2) -0.2158(9) 0.4942(19) 0.0216(14) Uani d . 1 . . C
  C21 0.9338(2) 0.5366(11) 0.7712(5) 0.0209(13) Uani d . 1 . . C
  C22 0.9396(2) 0.7336(11) 0.8643(6) 0.0206(13) Uani d . 1 . . C
  C23 0.9849(2) 0.8953(13) 0.8680(6) 0.0217(9) Uani d . 1 . . C
  C24 1.0273(2) 0.8620(11) 0.7729(6) 0.0217(9) Uani d . 1 . . C
  C25 1.0228(3) 0.6848(11) 0.6870(6) 0.0259(10) Uani d . 1 . . C
  C26 0.9777(2) 0.5148(11) 0.6803(6) 0.0259(10) Uani d . 1 . . C
  C27 0.8866(2) 0.3589(12) 0.7629(6) 0.0224(15) Uani d . 1 . . C
  H1 0.8136 0.0473 0.7395 0.029 Uiso calc R 1 . . H
  H2 0.8570 0.3748 0.8224 0.027 Uiso calc R 1 . . H
  H12 0.7567 -0.2975 0.6708 0.024 Uiso calc R 1 . . H
  H13 0.7396 -0.6307 0.5229 0.026 Uiso calc R 1 . . H
  H15 0.8816 -0.4445 0.3352 0.025 Uiso calc R 1 . . H
  H16 0.9003 -0.1126 0.4890 0.026 Uiso calc R 1 . . H
  H23 0.9883 1.0269 0.9318 0.026 Uiso calc R 1 . . H
  H24 1.0590 0.9732 0.7740 0.026 Uiso calc R 1 . . H
  H25 1.0514 0.6689 0.6253 0.031 Uiso calc R 1 . . H
  H26 0.9761 0.3843 0.6155 0.031 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
  I22 0.02463(18) 0.02820(19) 0.02070(17) 0.00047(14) 0.0017(3) -0.0016(4)
  O41 0.030(3) 0.027(2) 0.032(3) -0.010(2) -0.006(2) -0.003(2)
  O42 0.036(3) 0.045(3) 0.021(2) -0.004(2) 0.002(2) -0.012(2)
  N1 0.026(3) 0.029(3) 0.016(2) 0.000(2) 0.005(2) -0.003(2)
  N2 0.021(3) 0.014(3) 0.020(3) 0.000(2) -0.001(2) 0.003(2)
  N4 0.023(3) 0.027(3) 0.025(3) 0.007(2) -0.010(2) -0.001(2)
  C11 0.016(3) 0.017(3) 0.017(3) 0.000(2) -0.006(2) 0.006(3)
  C12 0.019(3) 0.022(4) 0.019(3) 0.002(3) 0.005(3) -0.003(3)
  C13 0.017(3) 0.023(3) 0.026(4) 0.0011(19) -0.006(3) 0.004(4)
  C14 0.022(3) 0.016(3) 0.018(3) 0.001(3) -0.005(3) 0.003(3)
  C15 0.022(3) 0.028(3) 0.013(3) 0.005(3) 0.001(3) 0.003(3)
  C16 0.016(3) 0.025(2) 0.023(4) -0.002(2) 0.008(5) 0.006(6)
  C21 0.022(3) 0.018(3) 0.023(3) 0.003(2) -0.005(3) 0.003(3)
  C22 0.019(3) 0.018(3) 0.024(3) 0.007(2) 0.000(3) -0.002(3)
  C23 0.013(2) 0.019(2) 0.034(2) -0.0023(17) -0.0059(18) 0.008(2)
  C24 0.013(2) 0.019(2) 0.034(2) -0.0023(17) -0.0059(18) 0.008(2)
  C25 0.021(2) 0.030(3) 0.027(2) 0.0056(17) 0.002(2) 0.012(2)
  C26 0.021(2) 0.030(3) 0.027(2) 0.0056(17) 0.002(2) 0.012(2)
  C27 0.021(3) 0.023(3) 0.023(3) 0.003(2) -0.003(3) 0.002(3)
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
  C11 C16 . 1.377(16) no
  C11 N1 . 1.380(7) no
  C11 C12 . 1.396(8) no
  C12 C13 . 1.375(8) no
  C12 H12 . 0.95 no
  C13 C14 . 1.384(8) no
  C13 H13 . 0.95 no
  C14 C15 . 1.391(8) no
  C14 N4 . 1.440(8) no
  N4 O41 . 1.229(7) no
  N4 O42 . 1.252(7) no
  C15 C16 . 1.409(16) no
  C15 H15 . 0.95 no
  C16 H16 . 0.95 no
  N1 N2 . 1.364(6) no
  N1 H1 . 0.88 no
  N2 C27 . 1.291(8) no
  C27 C21 . 1.454(8) no
  C27 H2 . 0.95 no
  C21 C22 . 1.405(8) no
  C21 C26 . 1.430(8) no
  C22 C23 . 1.364(8) no
  C22 I22 . 2.121(6) no
  C23 C24 . 1.439(8) no
  C23 H23 . 0.95 no
  C24 C25 . 1.278(8) no
  C24 H24 . 0.95 no
  C25 C26 . 1.387(8) no
  C25 H25 . 0.95 no
  C26 H26 . 0.95 no
_cod_database_code 2013209