data_2010697
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  365
_journal_page_last  368
_publ_section_title
;
Intermolecular interactions in the chiral and racemic forms of
3-hydroxy-2-(1-oxoisoindolin-2-yl)butanoic acid derived
from threonine
;
loop_
_publ_author_name
  'Gallagher, John F.'
  'Brady, Fiona'
  'Murphy, Carol'
_chemical_formula_moiety  'C12 H13 N O4 '
_chemical_formula_sum  'C12 H13 N O4 '
_chemical_formula_weight  235.23
_chemical_melting_point  459
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
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'
_cell_length_a  6.2209(6)
_cell_length_b  11.9726(13)
_cell_length_c  15.0705(12)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  1122.5(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  294.0(10)
_exptl_crystal_density_diffrn  1.392
_diffrn_ambient_temperature  294.0(10)
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  .5667(4)  .22403(18)  .98584(13)  .0491(6) Uani d . 1 . . O
  O2  .5280(4)  .37524(18)  .90086(15)  .0652(7) Uani d . 1 . . O
  O3  .2206(3)  .18768(18)  .71575(12)  .0457(5) Uani d . 1 . . O
  O4  .9620(3)  .1801(2)  .86098(13)  .0462(5) Uani d . 1 . . O
  N1  .5624(3)  .24890(18)  .74759(14)  .0349(5) Uani d . 1 . . N
  C1  .5560(5)  .2772(3)  .90909(18)  .0399(7) Uani d . 1 . . C
  C2  .5774(4)  .1939(2)  .83343(15)  .0339(6) Uani d . 1 . . C
  C3  .3828(4)  .2419(2)  .69714(16)  .0325(6) Uani d . 1 . . C
  C4  .4196(4)  .3118(2)  .61848(16)  .0320(6) Uani d . 1 . . C
  C5  .2828(5)  .3318(2)  .54723(17)  .0394(7) Uani d . 1 . . C
  C6  .3540(6)  .4043(3)  .48278(19)  .0499(9) Uani d . 1 . . C
  C7  .5552(6)  .4542(2)  .48836(18)  .0478(8) Uani d . 1 . . C
  C8  .6884(5)  .4343(2)  .55979(19)  .0425(8) Uani d . 1 . . C
  C9  .6180(4)  .3623(2)  .62557(17)  .0339(6) Uani d . 1 . . C
  C10  .7226(4)  .3259(2)  .71118(18)  .0383(7) Uani d . 1 . . C
  C11  .7722(4)  .1165(2)  .84408(16)  .0355(7) Uani d . 1 . . C
  C12  .7996(6)  .0391(2)  .76572(18)  .0471(8) Uani d . 1 . . C
  H1  .542(7)  .266(3) 1.027(3)  .091(14) Uiso d . 1 . . H
  H4 1.047(6)  .181(3)  .820(2)  .083(14) Uiso d . 1 . . H
  H2  .4508  .1455  .8375  .041 Uiso calc R 1 . . H
  H5  .1490  .2975  .5433  .047 Uiso calc R 1 . . H
  H6  .2658  .4203  .4346  .060 Uiso calc R 1 . . H
  H7  .6007  .5016  .4433  .057 Uiso calc R 1 . . H
  H8  .8224  .4684  .5637  .051 Uiso calc R 1 . . H
  H10A  .8583  .2884  .7003  .046 Uiso calc R 1 . . H
  H10B  .7465  .3888  .7505  .046 Uiso calc R 1 . . H
  H11  .7460  .0699  .8964  .043 Uiso calc R 1 . . H
  H12A  .9228  -.0077  .7751  .071 Uiso calc R 1 . . H
  H12B  .8198  .0824  .7127  .071 Uiso calc R 1 . . H
  H12C  .6737  -.0066  .7595  .071 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  .0561(14)  .0606(14)  .0306(11)  .0086(11)  .0091(11)  -.0019(10)
  O2  .091(2)  .0475(13)  .0569(14)  .0125(13)  .0100(13)  .0000(11)
  O3  .0331(11)  .0667(13)  .0372(10)  -.0122(12)  -.0003(9)  .0037(10)
  O4  .0330(11)  .0746(14)  .0309(11)  -.0032(12)  -.0020(10)  -.0073(10)
  N1  .0261(12)  .0471(13)  .0313(11)  -.0073(12)  -.0022(10)  .0094(10)
  C1  .0313(17)  .0486(18)  .0400(16)  .0024(15)  .0047(14)  .0020(13)
  C2  .0321(16)  .0435(15)  .0261(13)  -.0043(14)  .0031(11)  .0069(12)
  C3  .0276(15)  .0430(16)  .0269(13)  -.0026(14)  .0042(11)  -.0039(12)
  C4  .0337(17)  .0359(14)  .0265(13)  .0040(15)  .0012(11)  -.0025(11)
  C5  .0367(16)  .0482(18)  .0333(14)  .0002(15)  .0005(14)  -.0069(13)
  C6  .066(2)  .054(2)  .0292(15)  .0130(17)  -.0045(15)  .0001(14)
  C7  .068(2)  .0421(17)  .0333(15)  .0057(18)  .0108(17)  .0065(13)
  C8  .0454(19)  .0383(17)  .0437(17)  -.0049(14)  .0106(15)  .0052(13)
  C9  .0352(16)  .0333(14)  .0333(14)  .0031(13)  .0031(13)  -.0007(12)
  C10  .0295(15)  .0445(16)  .0409(14)  -.0063(15)  .0015(14)  .0074(13)
  C11  .0361(17)  .0412(16)  .0292(14)  -.0022(14)  .0030(12)  .0058(12)
  C12  .051(2)  .0486(18)  .0422(17)  .0009(16)  .0075(15)  -.0005(14)
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 . 1.322(3) yes
  O2 C1 . 1.193(3) yes
  O3 C3 . 1.232(3) yes
  O4 C11 . 1.427(3) yes
  N1 C2 . 1.454(3) yes
  N1 C3 . 1.354(3) yes
  N1 C10 . 1.465(3) yes
  C1 C2 . 1.520(4) yes
  C2 C11 . 1.534(4) yes
  C3 C4 . 1.469(4) yes
  C4 C5 . 1.391(4) no
  C4 C9 . 1.379(4) no
  C5 C6 . 1.376(4) no
  C6 C7 . 1.389(4) no
  C7 C8 . 1.379(4) no
  C8 C9 . 1.384(4) no
  C9 C10 . 1.509(4) yes
  C11 C12 . 1.511(3) yes