#------------------------------------------------------------------------------
#$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013802.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_2013802
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o24
_journal_page_last  o27
_publ_section_title
;
A three-dimensional hydrogen-bonded framework in N-(3-nitrophenyl)phthalimide
and hydrogen bonded chains of rings in N-(3,5-dinitrophenyl)phthalimide,
linked into sheets by dipolar interactions
;
_space_group_IT_number           7
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_[local]_cod_cif_authors_sg_H-M  'P n'
loop_
_publ_author_name
  'Glidewell, Christopher'
  'Low, John N.'
  'Skakle, Janet M. S.'
  'Wardell, James L.'
_chemical_formula_moiety  'C14 H8 N2 O4'
_chemical_formula_sum  'C14 H8 N2 O4'
_chemical_formula_iupac  'C14 H8 N2 O4'
_chemical_formula_weight  268.22
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x+1/2, -y, z+1/2'
_cell_length_a  6.6650(5)
_cell_length_b  3.6962(3)
_cell_length_c  23.639(2)
_cell_angle_alpha  90
_cell_angle_beta  95.208(3)
_cell_angle_gamma  90
_cell_volume  579.95(8)
_cell_formula_units_Z  2
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.536
_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 0.7445(5) 0.8585(9) 0.20877(15) 0.0279(8) Uani d . 1 . . N
  C1 0.5599(6) 1.0114(11) 0.22174(19) 0.0266(10) Uani d . 1 . . C
  O1 0.4373(4) 1.1439(8) 0.18681(12) 0.0306(7) Uani d . 1 . . O
  C2 0.8600(6) 0.7387(11) 0.25848(19) 0.0290(10) Uani d . 1 . . C
  O2 1.0213(4) 0.5878(8) 0.25924(13) 0.0359(7) Uani d . 1 . . O
  C3 0.5602(6) 0.9848(11) 0.28435(19) 0.0283(10) Uani d . 1 . . C
  C4 0.4130(6) 1.0903(11) 0.3188(2) 0.0297(10) Uani d . 1 . . C
  C5 0.4544(7) 1.0324(11) 0.3768(2) 0.0358(11) Uani d . 1 . . C
  C6 0.6376(7) 0.8856(12) 0.3991(2) 0.0365(11) Uani d . 1 . . C
  C7 0.7843(6) 0.7810(11) 0.36369(19) 0.0327(10) Uani d . 1 . . C
  C8 0.7405(6) 0.8316(10) 0.30614(18) 0.0270(9) Uani d . 1 . . C
  C11 0.8064(6) 0.8257(11) 0.15264(17) 0.0288(10) Uani d . 1 . . C
  C12 0.6746(6) 0.6874(10) 0.10976(18) 0.0255(9) Uani d . 1 . . C
  C13 0.7409(6) 0.6553(10) 0.05634(19) 0.0281(10) Uani d . 1 . . C
  C14 0.9339(6) 0.7516(12) 0.0448(2) 0.0303(10) Uani d . 1 . . C
  C15 1.0634(6) 0.8910(12) 0.08854(18) 0.0312(10) Uani d . 1 . . C
  C16 1.0007(6) 0.9310(11) 0.14216(19) 0.0287(10) Uani d . 1 . . C
  N13 0.6026(5) 0.5020(10) 0.01052(16) 0.0325(9) Uani d . 1 . . N
  O131 0.4289(4) 0.4367(11) 0.02037(13) 0.0487(9) Uani d . 1 . . O
  O132 0.6673(5) 0.4450(11) -0.03559(14) 0.0500(9) Uani d . 1 . . O
  H4 0.2901 1.1969 0.3035 0.036 Uiso calc R 1 . . H
  H5 0.3559 1.0941 0.4018 0.043 Uiso calc R 1 . . H
  H6 0.6631 0.8562 0.4390 0.044 Uiso calc R 1 . . H
  H7 0.9088 0.6794 0.3787 0.039 Uiso calc R 1 . . H
  H12 0.5421 0.6163 0.1168 0.031 Uiso calc R 1 . . H
  H14 0.9764 0.7226 0.0078 0.036 Uiso calc R 1 . . H
  H15 1.1963 0.9595 0.0815 0.037 Uiso calc R 1 . . H
  H16 1.0894 1.0300 0.1719 0.034 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 0.0226(18) 0.0291(19) 0.031(2) 0.0000(15) -0.0009(15) -0.0009(16)
  C1 0.022(2) 0.0186(19) 0.039(3) -0.0068(18) 0.0041(19) 0.0017(17)
  O1 0.0208(14) 0.0365(17) 0.0340(17) 0.0013(13) -0.0009(13) 0.0025(14)
  C2 0.026(2) 0.023(2) 0.038(3) -0.0040(19) 0.0001(18) -0.0035(19)
  O2 0.0290(17) 0.0361(16) 0.0418(19) 0.0078(14) -0.0015(13) -0.0009(15)
  C3 0.026(2) 0.023(2) 0.036(2) -0.0039(18) 0.0007(18) 0.0017(17)
  C4 0.027(2) 0.023(2) 0.038(3) 0.0013(18) -0.0022(19) 0.0004(19)
  C5 0.035(3) 0.035(2) 0.037(3) -0.002(2) 0.005(2) -0.001(2)
  C6 0.041(2) 0.036(2) 0.032(3) 0.001(2) -0.001(2) 0.002(2)
  C7 0.033(2) 0.027(2) 0.037(3) 0.003(2) -0.002(2) 0.0003(19)
  C8 0.025(2) 0.0208(19) 0.034(2) -0.0052(18) -0.0005(18) 0.0005(18)
  C11 0.027(2) 0.029(2) 0.029(3) 0.0054(19) -0.0028(18) 0.0016(18)
  C12 0.0183(18) 0.0214(19) 0.037(3) 0.0011(17) 0.0016(17) 0.0048(17)
  C13 0.029(2) 0.024(2) 0.030(2) -0.0037(18) -0.0030(19) -0.0008(18)
  C14 0.026(2) 0.033(2) 0.033(3) 0.0007(19) 0.0044(18) 0.0035(19)
  C15 0.0204(19) 0.033(2) 0.041(3) -0.0007(18) 0.0064(19) 0.0023(19)
  C16 0.023(2) 0.025(2) 0.038(3) 0.0017(18) -0.0011(19) -0.0022(18)
  N13 0.032(2) 0.035(2) 0.030(2) -0.0021(17) 0.0000(16) 0.0010(16)
  O131 0.0306(18) 0.076(3) 0.039(2) -0.0156(17) 0.0007(15) -0.0113(16)
  O132 0.0463(19) 0.073(2) 0.031(2) -0.0117(18) 0.0042(16) -0.0090(17)
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 . 1.413(5) no
  N1 C2 . 1.416(5) no
  N1 C11 . 1.430(5) no
  C1 O1 . 1.211(5) no
  C1 C3 . 1.483(6) no
  C2 O2 . 1.210(5) no
  C2 C8 . 1.478(6) no
  C3 C8 . 1.385(6) no
  C3 C4 . 1.386(6) no
  C4 C5 . 1.391(7) no
  C4 H4 . 0.95 no
  C5 C6 . 1.395(6) no
  C5 H5 . 0.95 no
  C6 C7 . 1.398(6) no
  C6 H6 . 0.95 no
  C7 C8 . 1.378(6) no
  C7 H7 . 0.95 no
  C11 C12 . 1.378(5) no
  C11 C16 . 1.396(6) no
  C12 C13 . 1.380(6) no
  C12 H12 . 0.95 no
  C13 C14 . 1.385(6) no
  C13 N13 . 1.471(5) no
  C14 C15 . 1.385(6) no
  C14 H14 . 0.95 no
  C15 C16 . 1.378(6) no
  C15 H15 . 0.95 no
  C16 H16 . 0.95 no
  N13 O131 . 1.226(4) no
  N13 O132 . 1.226(5) no
_cod_database_code 2013802