#------------------------------------------------------------------------------
#$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2200287.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_2200287
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o436
_journal_page_last  o438
_publ_section_title
;
3-Cyano-4-[2-(4-methylthiophenyl)ethenyl]-2H-1-benzopyran-2-one
;
loop_
_publ_author_name
  'Vijayalakshmi, L.'
  'Parthasarathi, V.'
  'Varu, Bharat'
  'Shah, Anamik'
_chemical_name_common
  '2-(3-cyano-coumarin-4-yl)-1-(4-methylthiophenyl)ethene'
_chemical_formula_moiety  'C19 H13 N O2 S'
_chemical_formula_sum  'C19 H13 N O2 S'
_chemical_formula_iupac  'C19 H13 N O2 S'
_chemical_formula_weight  319.36
_symmetry_cell_setting  'orthorhombic'
_symmetry_space_group_name_H-M  ' P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
  '-x+1/2, -y, z+1/2'
_cell_length_a  7.783(3)
_cell_length_b  7.8653(10)
_cell_length_c  25.610(3)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1567.7(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.353
_diffrn_ambient_temperature  293(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 1.0648(2)  -.2199(2)  -.13279(6)  .0528(4) Uani d . 1 . . O
  O2 1.2001(3)  -.3808(2)  -.07566(9)  .0698(6) Uani d . 1 . . O
  C2 1.1358(3)  -.2453(3)  -.08479(10)  .0490(6) Uani d . 1 . . C
  C3 1.1296(3)  -.1021(3)  -.04888(9)  .0414(5) Uani d . 1 . . C
  C4 1.0554(3)  .0500(3)  -.06072(8)  .0371(5) Uani d . 1 . . C
  C5  .9153(3)  .2224(3)  -.13167(10)  .0515(6) Uani d . 1 . . C
  H5  .9055  .3155  -.1095  .062 Uiso calc R 1 . . H
  C6  .8575(4)  .2338(4)  -.18233(11)  .0652(8) Uani d . 1 . . C
  H6  .8104  .3351  -.1944  .078 Uiso calc R 1 . . H
  C7  .8691(4)  .0966(4)  -.21505(10)  .0664(8) Uani d . 1 . . C
  H7  .8290  .1055  -.2491  .080 Uiso calc R 1 . . H
  C8  .9390(4)  -.0537(4)  -.19829(10)  .0585(7) Uani d . 1 . . C
  H8  .9467  -.1464  -.2207  .070 Uiso calc R 1 . . H
  C9  .9978(3)  -.0649(3)  -.14741(9)  .0458(5) Uani d . 1 . . C
  C10  .9890(3)  .0708(3)  -.11328(8)  .0398(5) Uani d . 1 . . C
  C11 1.0441(3)  .1887(3)  -.02313(8)  .0411(5) Uani d . 1 . . C
  H11 1.0725  .2981  -.0339  .049 Uiso calc R 1 . . H
  C12  .9943(3)  .1640(3)  .02616(8)  .0403(5) Uani d . 1 . . C
  H12  .9619  .0540  .0351  .048 Uiso calc R 1 . . H
  C13  .9033(3)  .2512(3)  .11423(8)  .0431(5) Uani d . 1 . . C
  H13  .8525  .1450  .1181  .052 Uiso calc R 1 . . H
  C14  .8963(3)  .3662(3)  .15478(9)  .0457(5) Uani d . 1 . . C
  H14  .8408  .3368  .1857  .055 Uiso calc R 1 . . H
  C15  .9714(3)  .5258(3)  .14991(8)  .0427(5) Uani d . 1 . . C
  C16 1.0529(3)  .5671(3)  .10343(9)  .0453(5) Uani d . 1 . . C
  H16 1.1035  .6735  .0996  .054 Uiso calc R 1 . . H
  C17 1.0595(3)  .4525(3)  .06319(9)  .0425(5) Uani d . 1 . . C
  H17 1.1147  .4827  .0323  .051 Uiso calc R 1 . . H
  C18  .9853(3)  .2915(3)  .06744(8)  .0385(5) Uani d . 1 . . C
  S19  .95810(10)  .66348(9)  .20370(2)  .0607(2) Uani d . 1 . . S
  C20 1.0518(7)  .8544(4)  .17999(13)  .0950(13) Uani d . 1 . . C
  H20A 1.1670  .8321  .1685  .142 Uiso calc R 1 . . H
  H20B 1.0537  .9377  .2074  .142 Uiso calc R 1 . . H
  H20C  .9852  .8967  .1512  .142 Uiso calc R 1 . . H
  C21 1.2179(3)  -.1305(3)  -.00056(10)  .0486(6) Uani d . 1 . . C
  N21 1.2917(3)  -.1535(4)  .03747(10)  .0690(7) Uani d . 1 . . N
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  .0611(10)  .0435(8)  .0539(9)  .0054(8)  .0076(8)  -.0097(7)
  O2  .0762(13)  .0436(10)  .0896(14)  .0212(10)  .0069(12)  -.0011(10)
  C2  .0455(12)  .0389(12)  .0626(14)  .0052(12)  .0094(12)  -.0007(11)
  C3  .0385(10)  .0374(11)  .0482(11)  .0002(10)  .0059(10)  .0038(9)
  C4  .0329(10)  .0348(10)  .0437(11)  .0002(10)  .0057(9)  .0006(9)
  C5  .0515(13)  .0486(13)  .0543(13)  .0106(12)  .0014(11)  .0042(11)
  C6  .0647(16)  .0729(18)  .0581(15)  .0163(16)  -.0057(14)  .0133(14)
  C7  .0621(16)  .090(2)  .0469(13)  .0039(17)  -.0062(13)  .0055(15)
  C8  .0568(14)  .0689(16)  .0498(13)  -.0037(15)  .0009(12)  -.0102(12)
  C9  .0394(12)  .0490(12)  .0491(12)  .0015(11)  .0073(10)  -.0033(10)
  C10  .0365(10)  .0417(11)  .0413(10)  .0019(10)  .0059(9)  .0022(9)
  C11  .0448(11)  .0346(10)  .0440(11)  .0017(10)  .0004(9)  -.0003(9)
  C12  .0386(10)  .0358(10)  .0465(11)  .0000(10)  -.0010(9)  -.0003(9)
  C13  .0454(12)  .0384(11)  .0455(11)  -.0009(10)  -.0009(10)  .0060(10)
  C14  .0499(13)  .0481(12)  .0391(11)  .0021(11)  .0029(10)  .0047(10)
  C15  .0461(12)  .0422(11)  .0397(10)  .0082(11)  -.0062(10)  -.0020(9)
  C16  .0502(12)  .0373(11)  .0484(11)  -.0022(11)  -.0010(11)  -.0015(9)
  C17  .0450(11)  .0416(11)  .0410(11)  -.0014(11)  .0029(10)  -.0003(9)
  C18  .0365(10)  .0380(10)  .0410(10)  .0028(9)  -.0023(9)  .0009(9)
  S19  .0782(5)  .0575(4)  .0464(3)  .0079(4)  -.0010(3)  -.0127(3)
  C20  .162(4)  .0479(15)  .0749(19)  -.008(3)  -.003(2)  -.0207(15)
  C21  .0421(11)  .0463(13)  .0575(14)  .0048(11)  .0056(11)  .0124(11)
  N21  .0589(13)  .0794(17)  .0685(14)  .0095(15)  -.0045(12)  .0250(14)
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 C2 . 1.363(3) ?
  O1 C9 . 1.378(3) ?
  O2 C2 . 1.200(3) ?
  C2 C3 . 1.455(3) ?
  C3 C4 . 1.362(3) ?
  C3 C21 . 1.433(3) ?
  C4 C10 . 1.451(3) ?
  C4 C11 . 1.458(3) ?
  C5 C6 . 1.376(4) ?
  C5 C10 . 1.405(3) ?
  C5 H5 .  .9300 ?
  C6 C7 . 1.369(4) ?
  C6 H6 .  .9300 ?
  C7 C8 . 1.370(4) ?
  C7 H7 .  .9300 ?
  C8 C9 . 1.384(3) ?
  C8 H8 .  .9300 ?
  C9 C10 . 1.381(3) ?
  C11 C12 . 1.335(3) ?
  C11 H11 .  .9300 ?
  C12 C18 . 1.459(3) ?
  C12 H12 .  .9300 ?
  C13 C14 . 1.378(3) ?
  C13 C18 . 1.394(3) ?
  C13 H13 .  .9300 ?
  C14 C15 . 1.390(3) ?
  C14 H14 .  .9300 ?
  C15 C16 . 1.388(3) ?
  C15 S19 . 1.755(2) ?
  C16 C17 . 1.370(3) ?
  C16 H16 .  .9300 ?
  C17 C18 . 1.396(3) ?
  C17 H17 .  .9300 ?
  S19 C20 . 1.777(4) ?
  C20 H20A .  .9600 ?
  C20 H20B .  .9600 ?
  C20 H20C .  .9600 ?
  C21 N21 . 1.145(3) ?
_cod_database_code 2200287