data_2013801
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o12
_journal_page_last  o14
_publ_section_title
;
Three-dimensional aggregation in 2-hydroxy-3-iodo-5-nitrobenzaldehyde
involving C-H...O, iodo-nitro and aromatic \p--\p stacking interactions,
and isolated dimers in disordered 2,4-diiodo-6-nitroanisole
;
loop_
_publ_author_name
  'Garden, Simon J.'
  'Cunha, Fernando R. da'
  'Glidewell, Christopher'
  'Low, John N.'
  'Skakle, Janet M. S.'
  'Wardell, James L.'
_chemical_formula_moiety  'C7 H5 I2 N O3'
_chemical_formula_sum  'C7 H5 I2 N O3'
_chemical_formula_weight  404.92
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  32.999(2)
_cell_length_b  4.2305(3)
_cell_length_c  14.8328(11)
_cell_angle_alpha  90
_cell_angle_beta  95.225(2)
_cell_angle_gamma  90
_cell_volume  2062.1(2)
_cell_formula_units_Z  8
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  2.609
_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
  C1 0.1408(2) 0.3638(13) 0.5217(3) 0.0539(15) Uani d D 1 . . C
  I1 0.14846(4) 0.5738(3) 0.64326(6) 0.0692(3) Uani d P 0.50 A -1 I
  N1 0.1473(4) 0.525(4) 0.6090(6) 0.113(2) Uani d PD 0.50 A -2 N
  O11 0.1770(3) 0.691(3) 0.6295(7) 0.113(2) Uani d PD 0.50 A -2 O
  O12 0.1220(3) 0.486(4) 0.6629(8) 0.113(2) Uani d PD 0.50 A -2 O
  C2 0.10114(19) 0.3350(13) 0.4756(4) 0.0488(14) Uani d . 1 A . C
  O21 0.06871(13) 0.4760(11) 0.5092(3) 0.0616(12) Uani d . 1 . . O
  C21 0.0465(2) 0.2755(19) 0.5662(5) 0.077(2) Uani d . 1 A . C
  C3 0.09815(15) 0.1894(15) 0.3909(4) 0.0518(15) Uani d D 1 . . C
  N3 0.0590(2) 0.162(4) 0.3371(6) 0.113(2) Uani d PD 0.50 A -1 N
  O31 0.0584(3) 0.149(4) 0.2548(7) 0.113(2) Uani d PD 0.50 A -1 O
  O32 0.0272(3) 0.140(4) 0.3726(7) 0.113(2) Uani d PD 0.50 A -1 O
  I3 0.04405(3) 0.1563(3) 0.31796(6) 0.0732(3) Uani d P 0.50 A -2 I
  C4 0.1321(2) 0.0604(15) 0.3566(4) 0.0590(17) Uani d . 1 A . C
  C5 0.17055(19) 0.0899(15) 0.4032(4) 0.0540(15) Uani d . 1 . . C
  I5 0.221995(15) -0.09284(11) 0.34922(4) 0.0749(2) Uani d . 1 A . I
  C6 0.1749(2) 0.2420(16) 0.4848(4) 0.0574(16) Uani d . 1 A . C
  H21A 0.0316 0.1199 0.5296 0.115 Uiso calc R 1 . . H
  H21B 0.0279 0.4016 0.5971 0.115 Uiso calc R 1 . . H
  H21C 0.0653 0.1718 0.6098 0.115 Uiso calc R 1 . . H
  H4 0.1292 -0.0474 0.3017 0.071 Uiso calc R 1 . . H
  H6 0.2006 0.2642 0.5157 0.069 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 0.070(4) 0.047(4) 0.045(3) 0.002(3) 0.007(3) 0.010(3)
  I1 0.0891(7) 0.0674(6) 0.0507(5) 0.0001(6) 0.0045(5) -0.0066(4)
  N1 0.085(4) 0.157(6) 0.095(4) -0.006(4) 0.000(4) -0.030(4)
  O11 0.085(4) 0.157(6) 0.095(4) -0.006(4) 0.000(4) -0.030(4)
  O12 0.085(4) 0.157(6) 0.095(4) -0.006(4) 0.000(4) -0.030(4)
  C2 0.056(4) 0.048(3) 0.044(3) 0.006(3) 0.015(3) 0.007(3)
  O21 0.060(3) 0.065(3) 0.063(3) 0.015(2) 0.021(2) 0.004(2)
  C21 0.067(5) 0.093(5) 0.074(5) 0.002(4) 0.033(4) 0.004(4)
  C3 0.048(3) 0.060(4) 0.048(3) -0.002(3) 0.007(3) 0.000(3)
  N3 0.085(4) 0.157(6) 0.095(4) -0.006(4) 0.000(4) -0.030(4)
  O31 0.085(4) 0.157(6) 0.095(4) -0.006(4) 0.000(4) -0.030(4)
  O32 0.085(4) 0.157(6) 0.095(4) -0.006(4) 0.000(4) -0.030(4)
  I3 0.0548(6) 0.1124(9) 0.0518(5) 0.0057(6) 0.0013(4) -0.0050(5)
  C4 0.070(4) 0.057(4) 0.053(4) 0.002(3) 0.025(3) -0.003(3)
  C5 0.053(4) 0.051(4) 0.062(4) 0.000(3) 0.027(3) 0.013(3)
  I5 0.0687(3) 0.0625(3) 0.0993(4) 0.0104(2) 0.0396(3) 0.0057(3)
  C6 0.054(4) 0.061(4) 0.059(4) 0.002(3) 0.013(3) 0.001(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
  C1 C6 . 1.394(9) no
  C1 C2 . 1.427(9) no
  C1 N1 . 1.4603(10) no
  C1 I1 . 2.005(5) no
  N1 O12 . 1.2203(10) no
  N1 O11 . 1.2205(10) no
  C2 O21 . 1.359(7) no
  C2 C3 . 1.394(8) no
  O21 C21 . 1.443(8) no
  C21 H21A . 0.96 no
  C21 H21B . 0.96 no
  C21 H21C . 0.96 no
  C3 C4 . 1.383(8) no
  C3 N3 . 1.4608(10) no
  C3 I3 . 2.007(5) no
  N3 O31 . 1.2202(10) no
  N3 O32 . 1.2204(10) no
  C4 C5 . 1.395(10) no
  C4 H4 . 0.93 no
  C5 C6 . 1.368(9) no
  C5 I5 . 2.090(6) no
  C6 H6 . 0.93 no