#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008450.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_2008450
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  761
_journal_page_last  764
_publ_section_title
;
Two novel 3,4-disubstituted-1,2,4-oxadiazole-5(4H)-thiones
;
loop_
_publ_author_name
  'Billodeaux, Damon R.'
  'Fronczek, Frank R.'
  'D\"ur\"u\,st, Ya\;sar'
_chemical_formula_moiety  'C10H11N3OS'
_chemical_formula_sum  'C10H11N3OS'
_chemical_formula_weight  221.28
_chemical_melting_point  '337-338 K'
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  '-x,-y,-z'
_cell_length_a  7.7280(10)
_cell_length_b  8.826(2)
_cell_length_c  9.3699(9)
_cell_angle_alpha  112.890(10)
_cell_angle_beta  112.029(9)
_cell_angle_gamma  94.840(10)
_cell_volume  525.6(4)
_cell_formula_units_z  2
_cell_measurement_temperature  100
_exptl_crystal_density_diffrn  1.399
_diffrn_ambient_temperature  100
_refine_ls_R_factor_obs  .044
_refine_ls_wR_factor_obs  .058
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_type_symbol
  S  .72448(6) 1.10791(5)  .96876(5)  .02200(10)
  Uij ? ? S
  O1  .3956(2)  .90370(10)
  .70540(10)
  .0189(4) Uij ? ? O
  N2  .2934(2)  .72790(10)
  .6032(2)  .0183(4) Uij ? ? N
  N4  .5816(2)  .76200(10)
  .80690(10)
  .0159(4) Uij ? ? N
  N7  .4790(2)  .39260(10)
  .67870(10)
  .0192(4) Uij ? ? N
  C3  .4093(2)  .6496(2)  .6692(2)  .0154(4) Uij ? ? C
  C5  .5692(2)  .9218(2)  .8291(2)  .0183(5) Uij ? ? C
  C6  .3536(2)  .4622(2)  .5975(2)  .0159(4) Uij ? ? C
  C8  .4279(2)  .2230(2)  .6157(2)  .0230(5) Uij ? ? C
  C9  .2542(2)  .1177(2)  .4734(2)  .0214(5) Uij ? ? C
  C10  .1272(2)  .1911(2)  .3909(2)  .0199(6) Uij ? ? C
  C11  .1764(2)  .3661(2)  .4526(2)  .0186(5) Uij ? ? C
  C12  .7529(2)  .7273(2)  .9147(2)  .0178(5) Uij ? ? C
  C13  .7343(2)  .7146(2) 1.0655(2)  .0204(5) Uij ? ? C
  C14  .8965(2)  .6478(2) 1.1534(2)  .0259(6) Uij ? ? C
  H8  .512(3)  .178(2)  .670(2)  .036(6) Uiso ? ? H
  H9  .224(3)  -.002(2)  .438(2)  .028(5) Uiso ? ? H
  H10  .012(3)  .125(2)  .296(2)  .033(6) Uiso ? ? H
  H11  .101(3)  .423(2)  .400(2)  .036(6) Uiso ? ? H
  H12a  .865(3)  .821(2)  .956(2)  .030(6) Uiso ? ? H
  H12b  .774(2)  .621(2)  .840(2)  .024(5) Uiso ? ? H
  H13b  .613(3)  .639(2) 1.025(2)  .029(5) Uiso ? ? H
  H13a  .739(3)  .826(3) 1.150(2)  .040(6) Uiso ? ? H
  H14b  .908(3)  .656(2) 1.267(2)  .035(6) Uiso ? ? H
  H14c  .885(3)  .542(3) 1.086(2)  .042(7) Uiso ? ? H
  H14a 1.014(3)  .708(2) 1.181(2)  .032(6) Uiso ? ? 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
_atom_site_aniso_type_symbol
  S  .02240(10)
  .01910(10)
  .02480(10)
  .00180(10)
  .00750(10)
  .00880(10)
  S
  O1  .0212(4)  .0139(3)  .0228(4)  .0039(3)  .0063(3)  .0098(3) O
  N2  .0214(5)  .0140(4)  .0204(4)  .0023(4)  .0055(4)  .0070(3) N
  N4  .0161(4)  .0139(4)  .0180(4)  .0035(4)  .0064(3)  .0080(3) N
  N7  .0232(5)  .0145(4)  .0211(4)  .0036(4)  .0074(4)  .0086(3) N
  C3  .0168(5)  .0148(4)  .0147(4)  .0022(4)  .0078(3)  .0066(3) C
  C5  .0194(5)  .0152(5)  .0207(4)  .0042(4)  .0105(4)  .0094(3) C
  C6  .0188(5)  .0143(5)  .0148(4)  .0038(4)  .0092(3)  .0063(3) C
  C8  .0296(6)  .0167(5)  .0246(5)  .0069(5)  .0105(4)  .0111(4) C
  C9  .0330(6)  .0138(5)  .0217(5)  .0013(5)  .0141(4)  .0041(4) C
  C10  .0241(6)  .0194(6)  .0170(5)  -.0003(5)  .0076(4)  .0020(4) C
  C11  .0205(5)  .0196(5)  .0160(4)  .0041(5)  .0069(4)  .0066(4) C
  C12  .0159(5)  .0178(5)  .0199(4)  .0045(4)  .0073(4)  .0096(3) C
  C13  .0224(6)  .0191(5)  .0200(5)  .0054(5)  .0101(4)  .0089(4) C
  C14  .0294(6)  .0271(6)  .0217(5)  .0111(5)  .0109(4)  .0131(4) C
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
  S C5 . . 1.6340(10)
  yes
  O1 N2 . . 1.4210(10)
  yes
  O1 C5 . . 1.350(2) yes
  N2 C3 . . 1.298(2) yes
  N4 C3 . . 1.3840(10)
  yes
  N4 C5 . . 1.360(2) yes
  N4 C12 . . 1.474(2) ?
  N7 C6 . . 1.344(2) ?
  N7 C8 . . 1.335(2) ?
  C3 C6 . . 1.473(2) yes
  C6 C11 . . 1.397(2) ?
  C8 C9 . . 1.388(2) ?
  C8 H8 . .  .89(2) ?
  C9 C10 . . 1.381(3) ?
  C9 H9 . .  .95(2) ?
  C10 C11 . . 1.380(2) ?
  C10 H10 . .  .920(10)
  ?
  C11 H11 . .  .93(2) ?
  C12 C13 . . 1.517(3) ?
  C12 H12a . .  .99(2) ?
  C12 H12b . . 1.00(2) ?
  C13 C14 . . 1.525(2) ?
  C13 H13b . .  .95(2) ?
  C13 H13a . .  .98(2) ?
  C14 H14b . . 1.01(2) ?
  C14 H14c . .  .87(2) ?
  C14 H14a . .  .90(2) ?