#------------------------------------------------------------------------------
#$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/25/2202554.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_2202554
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1012
_journal_page_last  o1013
_publ_section_title
;
2-[(2-Oxopyrrolidin-1-yl)carbonylmethyl]-2,3-dihydro-1H-isoindole-1,3-dione:
an anti-amnesic agent
;
loop_
_publ_author_name
  'Thamotharan, S.'
  'Parthasarathi, V.'
  'Gupta, P.'
  'Jindal, D. P.'
  'Piplani, P.'
  'Linden, Anthony'
_chemical_formula_moiety  'C14 H12 N2 O4'
_chemical_formula_sum  'C14 H12 N2 O4'
_chemical_formula_iupac  'C14 H12 N2 O4'
_chemical_formula_weight  272.26
_chemical_melting_point  473
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
  '-x+1/2, -y, z+1/2'
  '-x, -y, -z'
  '-x-1/2, y-1/2, z'
  'x, -y-1/2, z-1/2'
  'x-1/2, y, -z-1/2'
_cell_length_a  10.7480(2)
_cell_length_b  8.32800(10)
_cell_length_c  27.9084(4)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2498.06(7)
_cell_formula_units_Z  8
_cell_measurement_temperature  160(2)
_exptl_crystal_density_diffrn  1.448
_diffrn_ambient_temperature  160(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
  O1 -0.04618(14) 0.14043(17) 0.59049(5) 0.0458(4) Uani d . 1 . . O
  O3 0.27434(14) 0.49855(18) 0.58283(5) 0.0459(4) Uani d . 1 . . O
  O11 -0.01451(14) 0.48029(17) 0.66903(5) 0.0446(4) Uani d . 1 . . O
  O13 0.25931(14) 0.20034(18) 0.73247(5) 0.0481(4) Uani d . 1 . . O
  N2 0.11528(14) 0.32121(18) 0.59882(5) 0.0316(4) Uani d . 1 . . N
  N12 0.08877(15) 0.37071(17) 0.73097(5) 0.0308(4) Uani d . 1 . . N
  C1 0.02859(18) 0.2310(2) 0.57284(7) 0.0332(5) Uani d . 1 . . C
  C3 0.18932(19) 0.4147(2) 0.56920(7) 0.0328(5) Uani d . 1 . . C
  C4 0.1863(2) 0.4463(3) 0.47650(7) 0.0423(5) Uani d . 1 . . C
  H4 0.2515 0.5231 0.4752 0.051 Uiso calc R 1 . . H
  C5 0.1286(2) 0.3916(3) 0.43516(7) 0.0488(6) Uani d . 1 . . C
  H5 0.1540 0.4328 0.4050 0.059 Uiso calc R 1 . . H
  C6 0.0350(2) 0.2784(3) 0.43711(8) 0.0486(6) Uani d . 1 . . C
  H6 -0.0022 0.2422 0.4082 0.058 Uiso calc R 1 . . H
  C7 -0.0060(2) 0.2164(3) 0.48057(7) 0.0427(5) Uani d . 1 . . C
  H7 -0.0703 0.1382 0.4819 0.051 Uiso calc R 1 . . H
  C8 0.05035(19) 0.2726(2) 0.52169(6) 0.0329(5) Uani d . 1 . . C
  C9 0.14500(18) 0.3841(2) 0.51966(6) 0.0325(5) Uani d . 1 . . C
  C10 0.14576(19) 0.2922(2) 0.64844(6) 0.0345(5) Uani d . 1 . . C
  H101 0.2345 0.3186 0.6538 0.041 Uiso calc R 1 . . H
  H102 0.1342 0.1767 0.6556 0.041 Uiso calc R 1 . . H
  C11 0.06652(18) 0.3901(2) 0.68244(7) 0.0325(5) Uani d . 1 . . C
  C13 0.18439(19) 0.2856(2) 0.75308(7) 0.0369(5) Uani d . 1 . . C
  C14 0.1779(2) 0.3192(3) 0.80590(7) 0.0461(6) Uani d . 1 . . C
  H141 0.2411 0.3996 0.8154 0.055 Uiso calc R 1 . . H
  H142 0.1912 0.2198 0.8247 0.055 Uiso calc R 1 . . H
  C15 0.0468(2) 0.3842(3) 0.81345(7) 0.0473(6) Uani d . 1 . . C
  H151 -0.0123 0.2963 0.8207 0.057 Uiso calc R 1 . . H
  H152 0.0449 0.4632 0.8399 0.057 Uiso calc R 1 . . H
  C16 0.0154(2) 0.4634(2) 0.76604(7) 0.0384(5) Uani d . 1 . . C
  H161 -0.0747 0.4557 0.7591 0.046 Uiso calc R 1 . . H
  H162 0.0402 0.5779 0.7660 0.046 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
  O1 0.0429(9) 0.0496(9) 0.0450(9) -0.0089(8) -0.0024(7) 0.0101(7)
  O3 0.0514(10) 0.0470(9) 0.0394(9) -0.0128(8) -0.0014(7) -0.0051(7)
  O11 0.0486(9) 0.0499(9) 0.0352(9) 0.0154(8) -0.0018(7) 0.0027(7)
  O13 0.0457(9) 0.0581(9) 0.0405(9) 0.0131(8) -0.0038(7) 0.0012(7)
  N2 0.0375(10) 0.0346(9) 0.0228(9) -0.0010(8) 0.0002(7) 0.0002(7)
  N12 0.0390(9) 0.0301(8) 0.0233(9) 0.0015(8) 0.0002(7) 0.0004(7)
  C1 0.0342(11) 0.0327(11) 0.0327(11) 0.0026(9) -0.0023(9) 0.0009(9)
  C3 0.0385(12) 0.0297(10) 0.0302(11) 0.0024(9) 0.0018(9) -0.0028(9)
  C4 0.0486(13) 0.0461(13) 0.0322(12) 0.0052(11) 0.0062(10) 0.0033(10)
  C5 0.0617(16) 0.0573(14) 0.0275(12) 0.0177(13) 0.0019(11) 0.0030(10)
  C6 0.0585(15) 0.0562(14) 0.0310(12) 0.0165(13) -0.0097(11) -0.0104(11)
  C7 0.0475(13) 0.0435(12) 0.0370(12) 0.0064(10) -0.0102(10) -0.0083(10)
  C8 0.0383(11) 0.0324(11) 0.0280(11) 0.0069(9) -0.0028(9) -0.0029(8)
  C9 0.0397(11) 0.0318(10) 0.0260(11) 0.0053(9) 0.0007(9) -0.0010(8)
  C10 0.0391(11) 0.0389(11) 0.0254(11) 0.0029(9) -0.0025(9) 0.0004(9)
  C11 0.0347(11) 0.0328(10) 0.0302(11) -0.0007(10) -0.0002(9) 0.0020(9)
  C13 0.0392(12) 0.0351(11) 0.0366(12) -0.0025(10) 0.0007(10) -0.0002(10)
  C14 0.0574(14) 0.0510(13) 0.0299(12) -0.0032(12) -0.0063(10) 0.0010(10)
  C15 0.0654(15) 0.0459(13) 0.0305(12) 0.0023(12) 0.0042(11) -0.0025(10)
  C16 0.0461(13) 0.0344(11) 0.0346(12) 0.0002(10) 0.0070(10) -0.0046(9)
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
  O1 C1 . 1.207(2) ?
  O3 C3 . 1.211(2) ?
  O11 C11 . 1.209(2) ?
  O13 C13 . 1.218(2) ?
  N2 C3 . 1.387(2) ?
  N2 C1 . 1.399(2) ?
  N2 C10 . 1.443(2) ?
  N12 C11 . 1.385(2) ?
  N12 C13 . 1.392(3) ?
  N12 C16 . 1.475(2) ?
  C1 C8 . 1.488(3) ?
  C3 C9 . 1.484(3) ?
  C4 C9 . 1.384(3) ?
  C4 C5 . 1.387(3) ?
  C4 H4 . 0.9500 ?
  C5 C6 . 1.380(3) ?
  C5 H5 . 0.9500 ?
  C6 C7 . 1.390(3) ?
  C6 H6 . 0.9500 ?
  C7 C8 . 1.380(3) ?
  C7 H7 . 0.9500 ?
  C8 C9 . 1.379(3) ?
  C10 C11 . 1.514(3) ?
  C10 H101 . 0.9900 ?
  C10 H102 . 0.9900 ?
  C13 C14 . 1.502(3) ?
  C14 C15 . 1.524(3) ?
  C14 H141 . 0.9900 ?
  C14 H142 . 0.9900 ?
  C15 C16 . 1.516(3) ?
  C15 H151 . 0.9900 ?
  C15 H152 . 0.9900 ?
  C16 H161 . 0.9900 ?
  C16 H162 . 0.9900 ?
_cod_database_code 2202554