#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011395.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_2011395
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  1254
_journal_page_last  1257
_publ_section_title
;
Three leflunomide metabolite analogs
;
loop_
_publ_author_name
  'Ghosh, Sutapa'
  'Jennissen, Jason D.'
  'Zheng, Yaguo'
  'Uckun, Fatih M.'
_chemical_formula_moiety  'C12 H12 N2 O4 S'
_chemical_formula_sum  'C12 H12 N2 O4 S'
_chemical_formula_weight  280.30
_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  8.8002(10)
_cell_length_b  5.5336(6)
_cell_length_c  25.852(3)
_cell_angle_alpha  90.00
_cell_angle_beta  97.6440(10)
_cell_angle_gamma  90.00
_cell_volume  1247.7(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  295(2)
_exptl_crystal_density_diffrn  1.492
_diffrn_ambient_temperature  295(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
  S1  .92302(6)  .96106(9)  .186661(18)  .03941(17) Uani d . 1 . . S
  O1  .7903(2)  .8542(3)  .20405(7)  .0594(4) Uani d . 1 . . O
  O2 1.04355(19)  .8031(3)  .17545(6)  .0555(4) Uani d . 1 . . O
  O7  .82385(16) 1.4044(3)  -.06543(5)  .0446(4) Uani d . 1 . . O
  O9  .75956(19) 1.5746(3)  -.15671(6)  .0540(4) Uani d D 1 . . O
  H9  .799(3) 1.485(5)  -.1335(9)  .076(9) Uiso d D 1 . . H
  N1  .71869(19) 1.5741(3)  .00206(6)  .0389(4) Uani d D 1 . . N
  H1  .657(2) 1.682(3)  .0096(9)  .043(6) Uiso d D 1 . . H
  N11  .5095(2) 2.0899(4)  -.05154(8)  .0566(5) Uani d . 1 . . N
  C1  .7722(2) 1.4183(3)  .04377(7)  .0347(4) Uani d . 1 . . C
  C2  .8655(2) 1.2177(4)  .03973(8)  .0404(4) Uani d . 1 . . C
  H2  .8960 1.1769  .0078  .048 Uiso calc R 1 . . H
  C3  .9123(2) 1.0798(3)  .08344(8)  .0388(4) Uani d . 1 . . C
  H3  .9761  .9475  .0810  .047 Uiso calc R 1 . . H
  C4  .8650(2) 1.1370(3)  .13082(7)  .0337(4) Uani d . 1 . . C
  C5  .7714(2) 1.3354(4)  .13495(8)  .0413(5) Uani d . 1 . . C
  H5  .7389 1.3734  .1668  .050 Uiso calc R 1 . . H
  C6  .7270(2) 1.4751(4)  .09191(8)  .0422(5) Uani d . 1 . . C
  H6  .6658 1.6100  .0949  .051 Uiso calc R 1 . . H
  C7  .7434(2) 1.5618(3)  -.04842(8)  .0355(4) Uani d . 1 . . C
  C8  .6686(2) 1.7474(3)  -.08386(8)  .0366(4) Uani d . 1 . . C
  C9  .6804(2) 1.7415(4)  -.13599(8)  .0405(4) Uani d . 1 . . C
  C10  .6065(3) 1.9207(4)  -.17414(9)  .0530(6) Uani d . 1 . . C
  H10A  .5829 1.8454  -.2077  .079 Uiso calc R 1 . . H
  H10B  .6752 2.0537  -.1767  .079 Uiso calc R 1 . . H
  H10C  .5138 1.9788  -.1627  .079 Uiso calc R 1 . . H
  C11  .5806(2) 1.9372(4)  -.06545(8)  .0407(4) Uani d . 1 . . C
  C12  .9998(3) 1.1723(4)  .23398(8)  .0517(5) Uani d . 1 . . C
  H12A 1.0518 1.0884  .2637  .078 Uiso calc R 1 . . H
  H12B  .9184 1.2682  .2446  .078 Uiso calc R 1 . . H
  H12C 1.0710 1.2754  .2195  .078 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
  S1  .0506(3)  .0333(3)  .0355(3)  .0060(2)  .0100(2)  .00012(18)
  O1  .0708(10)  .0500(9)  .0616(10)  -.0100(8)  .0247(8)  .0067(8)
  O2  .0685(10)  .0520(9)  .0462(8)  .0283(8)  .0079(7)  .0012(7)
  O7  .0515(8)  .0398(8)  .0448(8)  .0173(6)  .0143(6)  .0045(6)
  O9  .0674(10)  .0517(9)  .0441(9)  .0244(8)  .0125(8)  .0043(7)
  N1  .0438(9)  .0332(8)  .0403(9)  .0129(7)  .0079(7)  -.0003(7)
  N11  .0625(12)  .0487(11)  .0594(12)  .0251(10)  .0112(10)  .0002(9)
  C1  .0353(9)  .0301(9)  .0388(10)  .0029(7)  .0055(7)  -.0017(7)
  C2  .0456(10)  .0404(10)  .0365(10)  .0123(9)  .0105(8)  -.0025(8)
  C3  .0431(10)  .0346(10)  .0397(10)  .0115(8)  .0088(8)  -.0017(8)
  C4  .0344(9)  .0309(9)  .0363(9)  .0017(7)  .0068(7)  -.0014(7)
  C5  .0488(11)  .0390(10)  .0378(10)  .0097(9)  .0122(9)  -.0038(8)
  C6  .0472(11)  .0352(10)  .0451(11)  .0141(9)  .0095(9)  -.0032(8)
  C7  .0339(9)  .0305(9)  .0425(10)  .0028(7)  .0063(8)  -.0001(8)
  C8  .0349(9)  .0312(9)  .0439(11)  .0053(8)  .0065(8)  .0009(8)
  C9  .0399(10)  .0371(10)  .0449(11)  .0073(8)  .0069(8)  .0021(8)
  C10  .0597(13)  .0518(13)  .0473(12)  .0182(11)  .0070(10)  .0093(10)
  C11  .0403(10)  .0379(10)  .0436(11)  .0072(8)  .0039(8)  .0036(8)
  C12  .0640(13)  .0536(13)  .0370(11)  .0040(11)  .0045(10)  -.0069(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
  S1 O2 . 1.4336(15) yes
  S1 O1 . 1.4339(16) yes
  S1 C4 . 1.7596(19) yes
  S1 C12 . 1.760(2) yes
  O7 C7 . 1.239(2) yes
  O9 C9 . 1.313(2) yes
  O9 H9 .  .819(10) yes
  N1 C7 . 1.353(3) yes
  N1 C1 . 1.412(2) yes
  N1 H1 .  .851(10) no
  N11 C11 . 1.138(2) yes
  C1 C6 . 1.392(3) no
  C1 C2 . 1.393(2) no
  C2 C3 . 1.380(3) no
  C2 H2 .  .9300 no
  C3 C4 . 1.382(3) no
  C3 H3 .  .9300 no
  C4 C5 . 1.385(3) no
  C5 C6 . 1.368(3) no
  C5 H5 .  .9300 no
  C6 H6 .  .9300 no
  C7 C8 . 1.472(3) yes
  C8 C9 . 1.366(3) yes
  C8 C11 . 1.424(3) yes
  C9 C10 . 1.486(3) yes
  C10 H10A .  .9600 no
  C10 H10B .  .9600 no
  C10 H10C .  .9600 no
  C12 H12A .  .9600 no
  C12 H12B .  .9600 no
  C12 H12C .  .9600 no