data_2012160
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  942
_journal_page_last  945
_publ_section_title
;
Triclinic and orthorhombic polymorphs of 2-iodo-4-nitroaniline: interplay
of hydrogen bonds, nitro...I interactions and aromatic \p...\p
stacking interactions
;
loop_
_publ_author_name
  'McWilliam, Susan A.'
  'Skakle, Janet M.S.'
  'Low, John N.'
  'Wardell, James L.'
  'Garden, Simon J.'
  'Pinto, Angelo C.'
  'Torres, Jose C.'
  'Glidewell, Christopher'
_chemical_formula_moiety  'C6 H5 I N2 O2'
_chemical_formula_sum  'C6 H5 I N2 O2'
_chemical_formula_weight  264.02
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, -y, -z'
  'x-1/2, y, -z-1/2'
  'x, -y-1/2, z-1/2'
  '-x-1/2, y-1/2, z'
_cell_length_a  7.4215(5)
_cell_length_b  12.6755(9)
_cell_length_c  16.4638(11)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1548.77(18)
_cell_formula_units_Z  8
_cell_measurement_temperature  296(2)
_exptl_crystal_density_diffrn  2.265
_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
  C1  .5827(11)  .4747(7)  .3056(5)  .0464(19) Uani d . 1 . . C
  N1  .5512(11)  .4240(6)  .3743(5)  .062(2) Uani d . 1 . . N
  C2  .6364(10)  .5828(7)  .3030(4)  .0427(19) Uani d . 1 . . C
  I2  .66772(8)  .66835(5)  .41043(3)  .0531(3) Uani d . 1 . . I
  C3  .6636(11)  .6331(6)  .2307(5)  .0426(17) Uani d . 1 . . C
  C4  .6401(11)  .5789(7)  .1593(5)  .0438(19) Uani d . 1 . . C
  N4  .6642(10)  .6332(7)  .0834(4)  .0529(18) Uani d . 1 . . N
  O1  .6825(10)  .7298(6)  .0850(4)  .0669(19) Uani d . 1 . . O
  O2  .6703(9)  .5836(6)  .0201(4)  .075(2) Uani d . 1 . . O
  C5  .5885(12)  .4739(8)  .1586(6)  .056(2) Uani d . 1 . . C
  C6  .5595(11)  .4233(7)  .2307(6)  .050(2) Uani d . 1 . . C
  H11  .5164  .3593  .3734  .075 Uiso calc R 1 . . H
  H12  .5655  .4557  .4201  .075 Uiso calc R 1 . . H
  H3  .6979  .7036  .2299  .051 Uiso calc R 1 . . H
  H5  .5737  .4383  .1096  .067 Uiso calc R 1 . . H
  H6  .5234  .3530  .2302  .060 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
  C1  .039(5)  .049(5)  .052(4)  .002(4)  -.003(4)  .005(4)
  N1  .057(5)  .067(5)  .062(4)  -.007(4)  -.010(4)  .025(4)
  C2  .027(4)  .062(5)  .039(4)  .009(3)  -.003(3)  -.003(4)
  I2  .0436(3)  .0690(5)  .0468(3)  .0027(3)  .0007(3)  -.0096(3)
  C3  .031(4)  .046(4)  .051(4)  .000(4)  .001(4)  .001(3)
  C4  .031(4)  .057(5)  .043(4)  .008(4)  -.001(3)  -.003(4)
  N4  .036(4)  .079(6)  .044(4)  .000(4)  .005(3)  .005(4)
  O1  .076(5)  .069(5)  .056(4)  .002(4)  .008(3)  .014(3)
  O2  .076(5)  .107(6)  .043(3)  -.001(4)  .011(3)  -.012(4)
  C5  .047(5)  .063(6)  .058(5)  -.002(4)  -.004(4)  -.014(4)
  C6  .041(5)  .043(5)  .067(5)  -.003(4)  -.006(4)  .003(4)
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
  C1 N1 . 1.323(10) no
  C1 C6 . 1.404(11) no
  C1 C2 . 1.428(12) no
  N1 H11 .  .8600 no
  N1 H12 .  .8600 no
  C2 C3 . 1.365(11) no
  C2 I2 . 2.087(8) no
  C3 C4 . 1.373(11) no
  C3 H3 .  .9300 no
  C4 C5 . 1.384(12) no
  C4 N4 . 1.439(10) no
  N4 O2 . 1.218(9) no
  N4 O1 . 1.231(12) no
  C5 C6 . 1.368(12) no
  C5 H5 .  .9300 no
  C6 H6 .  .9300 no