#------------------------------------------------------------------------------
#$Date: 2008-01-13 23:15:36 +0100 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2100141.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_2100141
_journal_name_full  'Acta Crystallographica, Section B'
_journal_year  2005
_journal_volume  61
_journal_page_first  227
_journal_page_last  237
_publ_section_title
;
Isomeric N-(iodophenyl)-nitrophthalimides: interplay of C-H...O
hydrogen bonds, iodo...nitro and iodo...carbonyl interactions,
and aromatic \p...\p stacking interactions
;
loop_
_publ_author_name
  'Glidewell, Christopher'
  'Low, John N.'
  'Skakle, Janet M.S.'
  'Wardell, Solange M. S. V.'
  'Wardell, James L.'
_chemical_formula_moiety  'C14 H7 I N2 O4'
_chemical_formula_sum  'C14 H7 I N2 O4'
_chemical_formula_weight  394.12
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x, -y+1/2, z+1/2'
  '-x, -y, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  7.9592(9)
_cell_length_b  6.5708(7)
_cell_length_c  25.648(3)
_cell_angle_alpha  90.00
_cell_angle_beta  97.960(3)
_cell_angle_gamma  90.00
_cell_volume  1328.4(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  291(2)
_exptl_crystal_density_diffrn  1.971
_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
  N1 0.2572(4) 0.3057(5) 0.23850(13) 0.0359(8) Uani d . 1 . . N
  C1 0.3679(6) 0.3800(7) 0.28155(19) 0.0469(12) Uani d . 1 . . C
  O1 0.4498(4) 0.5353(6) 0.28135(13) 0.0664(10) Uani d . 1 . . O
  C2 0.1811(5) 0.1229(7) 0.25127(18) 0.0392(11) Uani d . 1 . . C
  O2 0.0761(4) 0.0303(5) 0.22220(12) 0.0498(8) Uani d . 1 . . O
  C3 0.2518(5) 0.0768(7) 0.30601(17) 0.0418(11) Uani d . 1 . . C
  C4 0.2227(6) -0.0859(7) 0.3380(2) 0.0492(12) Uani d . 1 . . C
  C5 0.3031(6) -0.0746(8) 0.3891(2) 0.0519(13) Uani d . 1 . . C
  N5 0.2700(6) -0.2417(8) 0.4253(2) 0.0704(14) Uani d . 1 . . N
  O51 0.3144(5) -0.2137(7) 0.47317(17) 0.1032(15) Uani d . 1 . . O
  O52 0.2001(6) -0.3948(7) 0.40603(19) 0.0953(15) Uani d . 1 . . O
  C6 0.4063(6) 0.0804(9) 0.4095(2) 0.0590(14) Uani d . 1 . . C
  C7 0.4379(6) 0.2369(8) 0.3764(2) 0.0552(13) Uani d . 1 . . C
  C8 0.3598(6) 0.2327(7) 0.32509(18) 0.0428(12) Uani d . 1 . . C
  C11 0.2265(5) 0.3960(7) 0.18761(18) 0.0387(11) Uani d . 1 . . C
  C12 0.2393(5) 0.2767(7) 0.14373(17) 0.0411(11) Uani d . 1 . . C
  C13 0.1986(5) 0.3555(7) 0.09433(17) 0.0457(11) Uani d . 1 . . C
  C14 0.1423(6) 0.5562(8) 0.0878(2) 0.0530(13) Uani d . 1 . . C
  C15 0.1326(5) 0.6747(8) 0.1317(2) 0.0500(12) Uani d . 1 . . C
  C16 0.1756(5) 0.5957(7) 0.1812(2) 0.0471(12) Uani d . 1 . . C
  I13 0.21726(5) 0.16750(6) 0.029415(13) 0.06463(15) Uani d . 1 . . I
  H4 0.1537 -0.1950 0.3259 0.059 Uiso calc R 1 . . H
  H6 0.4538 0.0803 0.4447 0.071 Uiso calc R 1 . . H
  H7 0.5104 0.3429 0.3885 0.066 Uiso calc R 1 . . H
  H12 0.2758 0.1425 0.1480 0.049 Uiso calc R 1 . . H
  H14 0.1117 0.6094 0.0543 0.064 Uiso calc R 1 . . H
  H15 0.0966 0.8092 0.1276 0.060 Uiso calc R 1 . . H
  H16 0.1704 0.6773 0.2106 0.057 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
  N1 0.039(2) 0.033(2) 0.0355(19) -0.0005(18) 0.0049(16) -0.0012(17)
  C1 0.047(3) 0.044(3) 0.051(3) 0.000(3) 0.011(2) -0.004(2)
  O1 0.071(2) 0.064(3) 0.061(2) -0.029(2) -0.0007(18) 0.0007(19)
  C2 0.036(3) 0.036(3) 0.047(3) 0.002(2) 0.012(2) -0.009(2)
  O2 0.061(2) 0.0348(19) 0.053(2) -0.0075(17) 0.0065(17) -0.0059(16)
  C3 0.034(3) 0.048(3) 0.045(3) 0.009(2) 0.009(2) 0.005(2)
  C4 0.043(3) 0.045(3) 0.062(3) 0.007(2) 0.014(3) 0.002(2)
  C5 0.047(3) 0.061(4) 0.051(3) 0.019(3) 0.018(3) 0.016(3)
  N5 0.067(3) 0.072(4) 0.074(4) 0.016(3) 0.018(3) 0.031(3)
  O51 0.125(4) 0.126(4) 0.057(3) 0.001(3) 0.011(3) 0.040(3)
  O52 0.119(4) 0.069(3) 0.101(4) -0.009(3) 0.024(3) 0.024(3)
  C6 0.056(3) 0.076(4) 0.045(3) 0.010(3) 0.008(3) -0.002(3)
  C7 0.050(3) 0.060(3) 0.055(3) 0.000(2) 0.007(3) 0.003(3)
  C8 0.041(3) 0.050(3) 0.040(3) -0.002(2) 0.015(2) -0.001(2)
  C11 0.035(3) 0.034(3) 0.048(3) -0.003(2) 0.007(2) 0.001(2)
  C12 0.047(3) 0.032(3) 0.044(3) 0.003(2) 0.003(2) -0.002(2)
  C13 0.043(3) 0.048(3) 0.046(3) -0.009(3) 0.006(2) 0.003(2)
  C14 0.050(3) 0.056(4) 0.052(3) -0.009(3) 0.001(2) 0.018(3)
  C15 0.050(3) 0.033(3) 0.067(3) 0.002(3) 0.009(2) 0.006(3)
  C16 0.050(3) 0.035(3) 0.058(3) -0.005(2) 0.013(2) -0.003(2)
  I13 0.0827(3) 0.0657(3) 0.04511(19) -0.0086(2) 0.00785(16) -0.0063(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
  N1 C1 . 1.402(6) ?
  N1 C2 . 1.404(5) ?
  N1 C11 . 1.424(5) ?
  C1 O1 . 1.212(5) ?
  C1 C8 . 1.486(6) ?
  C2 O2 . 1.205(5) ?
  C2 C3 . 1.470(6) ?
  C3 C8 . 1.382(6) ?
  C3 C4 . 1.387(6) ?
  C4 C5 . 1.377(7) ?
  C4 H4 . 0.9300 ?
  C5 C6 . 1.366(7) ?
  C5 N5 . 1.486(6) ?
  N5 O52 . 1.221(6) ?
  N5 O51 . 1.243(6) ?
  C6 C7 . 1.378(6) ?
  C6 H6 . 0.9300 ?
  C7 C8 . 1.376(6) ?
  C7 H7 . 0.9300 ?
  C11 C16 . 1.376(6) ?
  C11 C12 . 1.387(6) ?
  C12 C13 . 1.366(6) ?
  C12 H12 . 0.9300 ?
  C13 C14 . 1.395(6) ?
  C13 I13 . 2.095(5) ?
  C14 C15 . 1.378(6) ?
  C14 H14 . 0.9300 ?
  C15 C16 . 1.373(6) ?
  C15 H15 . 0.9300 ?
  C16 H16 . 0.9300 ?