#------------------------------------------------------------------------------
#$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/06/2010698.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2010698
loop_
_publ_author_name
'Gallagher, John F.'
'Brady, Fiona'
'Murphy, Carol'
_publ_section_title
;
 Intermolecular interactions in the chiral and racemic forms of
 3-hydroxy-2-(1-oxoisoindolin-2-yl)butanoic acid derived from threonine
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              365
_journal_page_last               368
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C12 H13 N O4 '
_chemical_formula_sum            'C12 H13 N O4'
_chemical_formula_weight         235.23
_chemical_melting_point          426
_chemical_name_systematic
;
(2R/2S)-3-hydroxy-2-(1-oxoisoindolin-2-yl)butanoic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 93.131(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9772(7)
_cell_length_b                   14.3906(12)
_cell_length_c                   13.4926(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      18.34
_cell_measurement_theta_min      9.65
_cell_volume                     1158.8(2)
_computing_cell_refinement       'CAD-4-PC Software'
_computing_data_collection       'CAD-4-PC Software (Enraf-Nonius, 1992)'
_computing_data_reduction        'NRCVAX96 (Gabe et al., 1989)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEX (McArdle, 1995) and PLATON
(Spek, 1998)
;
_computing_publication_material
'NRCVAX96, SHELXL97 and PREP8 (Ferguson, 1998)'
_computing_structure_refinement  'NRCVAX96 and SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997b)'
_diffrn_ambient_temperature      294.0(10)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .7107
_diffrn_reflns_av_R_equivalents  .008
_diffrn_reflns_av_sigmaI/netI    .022
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2242
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         2.1
_diffrn_standards_decay_%        'variation <0.5'
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .102
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          .39
_exptl_crystal_size_mid          .35
_exptl_crystal_size_min          .21
_refine_diff_density_max         .16
_refine_diff_density_min         -.12
_refine_ls_extinction_coef       .044(3)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997a)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2155
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          .051
_refine_ls_R_factor_gt           .034
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0378P)^2^+0.2183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_ref         .086
_reflns_number_gt                1623
_reflns_number_total             2155
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bm1380.cif
_[local]_cod_data_source_block   II
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_[local]_cod_chemical_formula_sum_orig 'C12 H13 N O4 '
_cod_database_code               2010698
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'
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
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 -7 0
0 -6 3
1 -4 5
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C3 122.08(12) yes
C2 N1 C10 125.06(11) yes
C3 N1 C10 112.83(12) yes
O1 C1 O2 124.05(14) yes
O1 C1 C2 113.29(12) yes
O2 C1 C2 122.63(13) yes
N1 C2 C1 111.67(11) yes
N1 C2 C11 113.71(12) yes
C1 C2 C11 110.14(11) yes
O3 C3 N1 124.45(14) yes
O3 C3 C4 128.80(13) yes
N1 C3 C4 106.75(12) yes
C3 C4 C5 129.90(14) no
C3 C4 C9 108.60(12) no
C5 C4 C9 121.50(14) no
C4 C5 C6 117.75(15) no
C5 C6 C7 120.92(15) no
C6 C7 C8 121.21(16) no
C7 C8 C9 118.07(16) no
C4 C9 C8 120.55(14) no
C4 C9 C10 109.57(12) yes
C8 C9 C10 129.88(14) yes
N1 C10 C9 102.16(11) yes
O4 C11 C2 105.52(11) yes
O4 C11 C12 112.15(13) yes
C2 C11 C12 112.84(12) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O2 3_656 .82 1.82 2.6355(16) 175 yes
O4 H4 O3 4_566 .82 1.94 2.7423(15) 166 yes
C10 H10B O3 1_455 .97 2.48 3.3140(17) 144 yes
C11 H11 Cg2 4_666 .98 2.70 3.6440(16) 161 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 C2 C1 -112.29(14) yes
C10 N1 C2 C1 65.51(17) no
C3 N1 C2 C11 122.32(14) no
C10 N1 C2 C11 -59.88(18) no
O2 C1 C2 N1 -.2(2) no
O1 C1 C2 N1 178.16(13) yes
O2 C1 C2 C11 127.18(15) no
O1 C1 C2 C11 -54.49(17) no
C2 N1 C3 O3 1.4(2) no
C10 N1 C3 O3 -176.68(14) no
C2 N1 C3 C4 -178.81(12) no
C10 N1 C3 C4 3.14(16) no
O3 C3 C4 C9 177.43(15) no
N1 C3 C4 C9 -2.39(15) no
O3 C3 C4 C5 -2.5(3) no
N1 C3 C4 C5 177.73(14) no
C9 C4 C5 C6 .2(2) no
C3 C4 C5 C6 -179.93(14) no
C4 C5 C6 C7 -.4(2) no
C5 C6 C7 C8 .2(3) no
C6 C7 C8 C9 .3(2) no
C5 C4 C9 C8 .2(2) no
C3 C4 C9 C8 -179.67(13) no
C5 C4 C9 C10 -179.34(13) no
C3 C4 C9 C10 .77(16) no
C7 C8 C9 C4 -.4(2) no
C7 C8 C9 C10 179.01(15) no
C3 N1 C10 C9 -2.61(15) no
C2 N1 C10 C9 179.40(12) no
C4 C9 C10 N1 .99(15) no
C8 C9 C10 N1 -178.52(15) no
N1 C2 C11 O4 66.92(15) yes
C1 C2 C11 O4 -59.28(15) yes
N1 C2 C11 C12 -55.87(17) no
C1 C2 C11 C12 177.94(13) no
_cod_database_fobs_code 2010698
_journal_paper_doi 10.1107/S0108270199015619