#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008939.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_2008939
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  1598
_journal_page_last  1599
_publ_section_title
;
The absolute configuration of an intermediate cyclic sulfoximine in the
asymmetric synthesis of transition-state analog inhibitors of
\g-glutamylcysteine synthetase
;
loop_
_publ_author_name
  'Tokutake, Nobuya'
  'Hiratake, Jun'
  'Irie, Takayuki'
  'Yamano, Akihito'
  'Oda, Jun-ichi'
_chemical_formula_moiety  'C9 H16 N2 O4 S'
_chemical_formula_sum  'C9 H16 N2 O4 S'
_chemical_formula_weight  248.30
_chemical_melting_point  203
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
loop_
_symmetry_equiv_pos_as_xyz
  x,y,z
  -x,1/2+y,-z
_cell_length_a  10.5450(10)
_cell_length_b  9.7470(10)
_cell_length_c  5.3893(5)
_cell_angle_alpha  90
_cell_angle_beta  92.243(7)
_cell_angle_gamma  90
_cell_volume  553.50(10)
_cell_formula_units_Z  2
_cell_measurement_temperature  298.2
_exptl_crystal_density_diffrn  1.490
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
  S1 0.13861(3) 0.3065 0.13142(7) 0.02580(9) Uani d S 1.00 . . S
  O1 0.5629(2) 0.1212(2) 0.7394(2) 0.0387(4) Uani d . 1.00 . . O
  O2 0.48170(10)
  0.3332(2) 0.7372(2) 0.0331(3) Uani d . 1.00 . . O
  O3 0.1643(2) 0.2976(3) -0.1288(2) 0.0521(5) Uani d . 1.00 . . O
  O4 -0.13840(10)
  0.1538(2) 0.3845(4) 0.0561(5) Uani d . 1.00 . . O
  N1 0.58920(10)
  0.1140(2) 0.2484(2) 0.0234(3) Uani d . 1.00 . . N
  N2 0.0588(2) 0.1836(2) 0.2347(4) 0.0362(4) Uani d . 1.00 . . N
  C1 0.5192(2) 0.2271(2) 0.6355(3) 0.0237(3) Uani d . 1.00 . . C
  C2 0.50670(10)
  0.2233(2) 0.3494(3) 0.0209(3) Uani d . 1.00 . . C
  C3 0.3698(2) 0.1971(2) 0.2573(3) 0.0239(3) Uani d . 1.00 . . C
  C4 0.28440(10)
  0.3193(2) 0.3077(3) 0.0263(3) Uani d . 1.00 . . C
  C5 0.0442(2) 0.4503(2) 0.2065(4) 0.0307(4) Uani d . 1.00 . . C
  C6 -0.0626(2) 0.3874(2) 0.3512(3) 0.0298(4) Uani d . 1.00 . . C
  C7 -0.0529(2) 0.2312(2) 0.3247(4) 0.0317(4) Uani d . 1.00 . . C
  C8 -0.1958(2) 0.4361(3) 0.2710(5) 0.0404(5) Uani d . 1.00 . . C
  C9 -0.2331(2) 0.3969(3) 0.0077(5) 0.0486(6) Uani d . 1.00 . . C
  H1 0.5657 0.0289 0.2878 0.0281 Uiso d . 1.00 . . H
  H2 0.5790 0.1192 0.0940 0.0281 Uiso d . 1.00 . . H
  H3 0.6722 0.1232 0.3048 0.0281 Uiso d . 1.00 . . H
  H4 0.5324 0.3061 0.2827 0.0443 Uiso d . 1.00 . . H
  H5 0.3368 0.1102 0.3239 0.0443 Uiso d . 1.00 . . H
  H6 0.3665 0.1810 0.0839 0.0443 Uiso d . 1.00 . . H
  H7 0.2627 0.3165 0.4935 0.0443 Uiso d . 1.00 . . H
  H8 0.3263 0.4005 0.2590 0.0443 Uiso d . 1.00 . . H
  H9 -0.2518 0.3966 0.3812 0.0443 Uiso d . 1.00 . . H
  H10 -0.1926 0.5334 0.2874 0.0443 Uiso d . 1.00 . . H
  H11 0.0137 0.4864 0.0389 0.0443 Uiso d . 1.00 . . H
  H12 0.0938 0.5153 0.3216 0.0443 Uiso d . 1.00 . . H
  H13 -0.2122 0.3053 -0.0273 0.0583 Uiso d . 1.00 . . H
  H14 -0.3212 0.3964 -0.0571 0.0583 Uiso d . 1.00 . . H
  H15 -0.1942 0.4348 -0.0989 0.0583 Uiso d . 1.00 . . H
  H16 -0.0483 0.4127 0.5296 0.0443 Uiso d . 1.00 . . 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
  S1 0.0205(2) 0.0328(2) 0.0239(2) 0.0019(2) -0.00240(10)
  -0.0030(2)
  O1 0.0608(9) 0.0373(8) 0.0181(5) 0.0181(7) 0.0014(6) 0.0020(5)
  O2 0.0392(7) 0.0332(8) 0.0265(6) 0.0067(6) -0.0026(5) -0.0065(5)
  O3 0.0435(8) 0.0890(10)
  0.0236(6) 0.0120(10)
  -0.0013(5) -0.0076(9)
  O4 0.0301(8) 0.0540(10)
  0.0830(10)
  -0.0119(7) -0.0094(8) 0.0359(10)
  N1 0.0232(6) 0.0303(7) 0.0166(5) 0.0020(5) 0.0010(4) 0.0009(5)
  N2 0.0267(8) 0.0256(8) 0.0560(10)
  0.0002(6) -0.0066(7) -0.0023(7)
  C1 0.0238(7) 0.0310(8) 0.0160(6) -0.0009(6) -0.0014(5) -0.0003(6)
  C2 0.0191(6) 0.0260(7) 0.0175(6) -0.0008(5) 0.0000(5) 0.0019(5)
  C3 0.0200(6) 0.0308(8) 0.0208(6) -0.0025(6) -0.0018(5) -0.0017(6)
  C4 0.0188(6) 0.0328(8) 0.0271(7) -0.0007(7) -0.0021(5) -0.0038(7)
  C5 0.0244(8) 0.0243(8) 0.0432(10) -0.0001(7) -0.0015(7) -0.0008(7)
  C6 0.0268(8) 0.0368(10) 0.0259(8) 0.0006(7) 0.0024(6) -0.0030(7)
  C7 0.0234(8) 0.0326(9) 0.0382(9) -0.0034(7) -0.0081(7) 0.0112(8)
  C8 0.0240(8) 0.0390(10)
  0.0590(10)
  0.0053(8) 0.0074(8) 0.0014(10)
  C9 0.0350(10)
  0.0510(10)
  0.0590(10)
  -0.0087(10) -0.0161(9) 0.0230(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  S1 O3 . . 1.4410(10)
  yes
  S1 N2 . . 1.577(2) yes
  S1 C4 . . 1.780(2) yes
  S1 C5 . . 1.775(2) yes
  O1 C1 . . 1.253(2) no
  O2 C1 . . 1.242(2) no
  O4 C7 . . 1.228(3) no
  N1 C2 . . 1.492(2) no
  N1 H1 . . 0.893 no
  N1 H2 . . 0.837 no
  N1 H3 . . 0.919 no
  N2 C7 . . 1.373(3) no
  C1 C2 . . 1.543(2) no
  C2 C3 . . 1.530(2) no
  C2 H4 . . 0.928 no
  C3 C4 . . 1.524(3) no
  C3 H5 . . 0.988 no
  C3 H6 . . 0.947 no
  C4 H7 . . 1.037 no
  C4 H8 . . 0.948 no
  C5 C6 . . 1.524(3) no
  C5 H11 . . 1.010 no
  C5 H12 . . 1.017 no
  C6 C7 . . 1.533(3) no
  C6 C8 . . 1.528(3) no
  C6 H16 . . 0.998 no
  C8 C9 . . 1.507(4) no
  C8 H9) . . 0.937 no
  C8 H10 . . 0.953 no
  C9 H13 . . 0.940 no
  C9 H14 . . 0.980 no
  C9 H15 . . 0.808 no