data_2010698
_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  426
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  5.9772(7)
_cell_length_b  14.3906(12)
_cell_length_c  13.4926(16)
_cell_angle_alpha  90
_cell_angle_beta  93.131(7)
_cell_angle_gamma  90
_cell_volume  1158.8(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  294.0(10)
_exptl_crystal_density_diffrn  1.348
_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  .7516(2)  .03436(8)  .56714(10)  .0616(4) Uani d . 1 . . O
  O2  .5252(2)  .10744(8)  .45658(9)  .0572(4) Uani d . 1 . . O
  O3 1.06897(17)  .26222(9)  .36942(8)  .0515(3) Uani d . 1 . . O
  O4  .64987(17)  .23198(9)  .67140(7)  .0499(3) Uani d . 1 . . O
  N1  .77066(19)  .26700(8)  .46910(8)  .0351(3) Uani d . 1 . . N
  C1  .6886(3)  .10627(10)  .51494(10)  .0391(4) Uani d . 1 . . C
  C2  .8424(2)  .18912(10)  .53093(10)  .0353(3) Uani d . 1 . . C
  C3  .8919(2)  .29767(10)  .39366(10)  .0362(3) Uani d . 1 . . C
  C4  .7708(2)  .37805(10)  .34954(10)  .0374(3) Uani d . 1 . . C
  C5  .8271(3)  .43616(12)  .27247(11)  .0480(4) Uani d . 1 . . C
  C6  .6815(3)  .50705(12)  .24593(12)  .0547(5) Uani d . 1 . . C
  C7  .4848(3)  .51948(11)  .29424(13)  .0549(5) Uani d . 1 . . C
  C8  .4288(3)  .46136(11)  .37064(12)  .0486(4) Uani d . 1 . . C
  C9  .5754(2)  .39037(10)  .39802(10)  .0374(3) Uani d . 1 . . C
  C10  .5612(2)  .31874(10)  .47769(11)  .0394(4) Uani d . 1 . . C
  C11  .8693(2)  .21278(10)  .64189(10)  .0379(3) Uani d . 1 . . C
  C12 1.0275(3)  .29277(12)  .66338(13)  .0564(5) Uani d . 1 . . C
  H1  .6621  -.0081  .5566  .092 Uiso calc R 1 . . H
  H4  .6496  .2320  .7322  .075 Uiso calc R 1 . . H
  H2  .9903  .1703  .5101  .042 Uiso calc R 1 . . H
  H5  .9587  .4274  .2400  .058 Uiso calc R 1 . . H
  H6  .7155  .5472  .1949  .066 Uiso calc R 1 . . H
  H7  .3887  .5678  .2749  .066 Uiso calc R 1 . . H
  H8  .2965  .4698  .4027  .058 Uiso calc R 1 . . H
  H10A  .5545  .3473  .5426  .047 Uiso calc R 1 . . H
  H10B  .4316  .2789  .4657  .047 Uiso calc R 1 . . H
  H11  .9267  .1579  .6780  .046 Uiso calc R 1 . . H
  H12A 1.0305  .3074  .7329  .085 Uiso calc R 1 . . H
  H12B  .9774  .3460  .6255  .085 Uiso calc R 1 . . H
  H12C 1.1753  .2758  .6454  .085 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  .0779(9)  .0384(6)  .0656(8)  -.0105(6)  -.0225(7)  .0102(6)
  O2  .0691(8)  .0410(7)  .0587(7)  -.0062(6)  -.0216(6)  .0013(5)
  O3  .0415(6)  .0749(8)  .0393(6)  .0087(6)  .0124(5)  .0118(5)
  O4  .0493(6)  .0704(8)  .0310(6)  .0003(6)  .0095(5)  .0012(5)
  N1  .0368(6)  .0383(7)  .0307(6)  .0014(5)  .0076(5)  .0042(5)
  C1  .0516(9)  .0346(8)  .0308(7)  .0022(7)  .0005(7)  -.0017(6)
  C2  .0383(8)  .0365(8)  .0314(7)  .0019(6)  .0054(6)  .0026(6)
  C3  .0361(8)  .0452(9)  .0273(7)  -.0053(7)  .0023(6)  -.0005(6)
  C4  .0420(8)  .0403(8)  .0298(7)  -.0081(6)  .0002(6)  -.0001(6)
  C5  .0543(9)  .0515(10)  .0383(8)  -.0105(8)  .0034(7)  .0071(8)
  C6  .0787(12)  .0436(9)  .0411(9)  -.0127(9)  -.0020(9)  .0104(7)
  C7  .0794(12)  .0352(9)  .0486(10)  .0067(8)  -.0090(9)  .0002(7)
  C8  .0570(10)  .0417(9)  .0472(9)  .0069(8)  .0022(8)  -.0024(7)
  C9  .0452(8)  .0344(8)  .0325(7)  -.0032(6)  .0007(6)  -.0031(6)
  C10  .0412(8)  .0400(8)  .0377(8)  .0030(6)  .0086(6)  .0021(7)
  C11  .0412(8)  .0392(8)  .0333(7)  -.0031(7)  .0010(6)  .0023(6)
  C12  .0588(11)  .0554(11)  .0540(10)  -.0152(9)  -.0059(8)  -.0031(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 . 1.2961(17) yes
  O2 C1 . 1.2210(18) yes
  O3 C3 . 1.2350(17) yes
  O4 C11 . 1.4187(17) yes
  N1 C2 . 1.4481(18) yes
  N1 C3 . 1.3552(17) yes
  N1 C10 . 1.4669(18) yes
  C1 C2 . 1.514(2) yes
  C2 C11 . 1.535(2) yes
  C3 C4 . 1.473(2) yes
  C4 C5 . 1.390(2) no
  C4 C9 . 1.381(2) no
  C5 C6 . 1.375(2) no
  C6 C7 . 1.387(3) no
  C7 C8 . 1.383(2) no
  C8 C9 . 1.383(2) no
  C9 C10 . 1.495(2) yes
  C11 C12 . 1.508(2) yes