#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008449.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_2008449
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  761
_journal_page_last  764
_publ_section_title
;
Two novel 3,4-disubstituted-1,2,4-oxadiazole-5(4H)-thiones
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
  'Billodeaux, Damon R.'
  'Fronczek, Frank R.'
  'D\"ur\"u\,st, Ya\;sar'
_chemical_formula_moiety  'C14 H11 N3 O S'
_chemical_formula_sum  'C14 H11 N3 O S'
_chemical_formula_weight  269.32
_chemical_melting_point  '432-433 K'
_symmetry_cell_setting  Monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  16.234(3)
_cell_length_b  11.017(2)
_cell_length_c  7.1954(14)
_cell_angle_alpha  90
_cell_angle_beta  93.15(3)
_cell_angle_gamma  90
_cell_volume  1285.0(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  293
_exptl_crystal_density_diffrn  1.392
_diffrn_ambient_temperature  293
_refine_ls_R_factor_obs  .070
_refine_ls_wR_factor_obs  .169
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  S1  .67762(6)  .65482(11)  .19302(11)  .0849(4) Uani d . 1 . S
  O5  .82686(13)  .6875(3)  .3410(3)  .0721(6) Uani d . 1 . O
  N2  .76008(12)  .5486(2)  .4905(3)  .0542(6) Uani d . 1 . N
  N4  .88068(15)  .6417(3)  .4918(4)  .0727(8) Uani d . 1 . N
  N9  .8504(2)  .4435(3) 1.0591(4)  .0863(10) Uani d . 1 . N
  C3  .83771(15)  .5615(3)  .5723(4)  .0584(7) Uani d . 1 . C
  C6  .7530(2)  .6282(3)  .3431(4)  .0651(8) Uani d . 1 . C
  C7  .86800(15)  .4928(3)  .7397(4)  .0590(7) Uani d . 1 . C
  C8  .8262(2)  .4995(4)  .9018(4)  .0709(9) Uani d . 1 . C
  H8  .7783(2)  .5459(4)  .9007(4)  .085 Uiso calc R 1 . H
  C10  .9198(3)  .3787(4) 1.0539(7)  .0955(13) Uani d . 1 . C
  H10  .9385(3)  .3391(4) 1.1623(7)  .115 Uiso calc R 1 . H
  C11  .9655(2)  .3662(4)  .8999(7)  .0951(13) Uani d . 1 . C
  H11 1.0129(2)  .3187(4)  .9041(7)  .114 Uiso calc R 1 . H
  C12  .9394(2)  .4260(4)  .7393(5)  .0766(10) Uani d . 1 . C
  H12  .9694(2)  .4213(4)  .6331(5)  .092 Uiso calc R 1 . H
  C13  .70142(14)  .4562(3)  .5296(3)  .0518(7) Uani d . 1 . C
  C14  .62603(14)  .4876(3)  .5962(3)  .0579(7) Uani d . 1 . C
  H14  .61318(14)  .5682(3)  .6200(3)  .069 Uiso calc R 1 . H
  C15  .57021(15)  .3956(3)  .6266(3)  .0603(8) Uani d . 1 . C
  H15  .51887(15)  .4159(3)  .6689(3)  .072 Uiso calc R 1 . H
  C16  .58818(15)  .2744(3)  .5961(3)  .0570(8) Uani d . 1 . C
  C17  .6655(2)  .2454(3)  .5336(3)  .0610(7) Uani d . 1 . C
  H17  .6794(2)  .1646(3)  .5147(3)  .073 Uiso calc R 1 . H
  C18  .7215(2)  .3357(3)  .4997(4)  .0582(8) Uani d . 1 . C
  H18  .7728(2)  .3158(3)  .4567(4)  .070 Uiso calc R 1 . H
  C19  .5268(2)  .1749(4)  .6258(4)  .0740(10) Uani d . 1 . C
  H19A  .5546(3)  .1068(9)  .684(3)  .111 Uiso calc R 1 . H
  H19B  .5016(12)  .1504(17)  .5080(5)  .111 Uiso calc R 1 . H
  H19C  .4851(9)  .2041(8)  .704(3)  .111 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  .0871(7)  .1010(10)  .0670(5)  .0175(5)  .0085(4)  .0179(4)
  O5  .0750(13)  .069(2)  .0740(12)  -.0098(12)  .0215(10)  .0078(11)
  N2  .0477(10)  .062(2)  .0536(10)  .0020(11)  .0086(8)  .0035(10)
  N4  .0602(13)  .082(2)  .077(2)  -.0118(14)  .0170(12)  -.0009(14)
  N9  .088(2)  .090(3)  .079(2)  -.010(2)  -.0148(14)  .016(2)
  C3  .0453(12)  .066(2)  .0653(14)  -.0011(13)  .0118(10)  -.0060(13)
  C6  .067(2)  .070(2)  .0593(14)  .005(2)  .0181(12)  .0034(14)
  C7  .0454(12)  .060(2)  .0713(15)  -.0043(13)  -.0023(10)  -.0044(14)
  C8  .0558(14)  .087(3)  .070(2)  -.002(2)  -.0012(12)  .004(2)
  C10  .104(3)  .072(3)  .106(3)  -.012(3)  -.042(2)  .008(2)
  C11  .075(2)  .071(3)  .135(3)  .014(2)  -.039(2)  -.010(3)
  C12  .0527(15)  .074(2)  .102(2)  .002(2)  -.0039(14)  -.017(2)
  C13  .0430(12)  .065(2)  .0472(11)  -.0007(13)  .0013(9)  .0017(12)
  C14  .0489(13)  .067(2)  .0580(13)  .0074(14)  .0065(10)  .0030(13)
  C15  .0422(12)  .083(2)  .0567(13)  .0027(14)  .0069(10)  .0051(15)
  C16  .0506(13)  .076(2)  .0438(10)  -.0083(14)  -.0030(9)  .0035(12)
  C17  .0577(15)  .067(2)  .0575(13)  -.0034(15)  -.0017(11)  -.0030(14)
  C18  .0448(12)  .070(2)  .0597(13)  .0041(14)  .0058(10)  -.0037(13)
  C19  .066(2)  .095(3)  .0607(15)  -.021(2)  -.0014(12)  .008(2)
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 C6 . 1.614(3) yes
  O5 C6 . 1.366(4) yes
  O5 N4 . 1.446(3) yes
  N2 C3 . 1.369(3) yes
  N2 C6 . 1.376(4) yes
  N2 C13 . 1.433(3) yes
  N4 C3 . 1.283(4) yes
  N9 C8 . 1.329(4) no
  N9 C10 . 1.336(5) no
  C3 C7 . 1.483(4) yes
  C7 C12 . 1.373(4) no
  C7 C8 . 1.384(4) no
  C10 C11 . 1.374(6) no
  C11 C12 . 1.377(6) no
  C13 C14 . 1.383(3) no
  C13 C18 . 1.386(4) no
  C14 C15 . 1.384(4) no
  C15 C16 . 1.388(5) no
  C16 C17 . 1.393(4) no
  C16 C19 . 1.504(4) no
  C17 C18 . 1.378(4) no
_cod_database_code 2008449