#------------------------------------------------------------------------------
#$Date: 2008-11-20 21:58:43 +0200 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2008332.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_2008332
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  561
_journal_page_last  563
_publ_section_title
;
3-Cyano-5-(4-methoxybenzyl)-6-(4-methoxyphenyl)-4-methylthio-2H-pyran-2-one
;
loop_
_publ_author_name
  'Kumar, Rajesh'
  'Parmar, Virinder S.'
  'Errington, William'
_chemical_formula_sum  'C22 H19 N O4 S'
_chemical_formula_weight  393.44
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P n a 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, z+1/2'
  'x+1/2, -y+1/2, z'
  '-x+1/2, y+1/2, z+1/2'
_cell_length_a  20.5254(13)
_cell_length_b  15.1311(10)
_cell_length_c  6.1276(4)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1903.1(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  180(2)
_exptl_crystal_density_diffrn  1.373
_diffrn_ambient_temperature  180(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 0.49287(3) 0.27288(4) 0.35627(13) 0.04047(18) Uani d . 1 . . S
  O1 0.66599(8) 0.40816(10) 0.6612(3) 0.0306(4) Uani d . 1 . . O
  O2 0.66144(10) 0.52299(11) 0.4415(3) 0.0425(5) Uani d . 1 . . O
  O3 0.60636(10) -0.13998(12) 0.4887(4) 0.0486(6) Uani d . 1 . . O
  O4 0.80014(11) 0.21949(12) 1.4355(3) 0.0473(5) Uani d . 1 . . O
  N1 0.55646(12) 0.48731(18) 0.0201(5) 0.0533(7) Uani d . 1 . . N
  C2 0.63757(13) 0.45286(16) 0.4886(4) 0.0309(6) Uani d . 1 . . C
  C3 0.58436(12) 0.40918(15) 0.3825(4) 0.0277(5) Uani d . 1 . . C
  C4 0.55858(12) 0.33161(15) 0.4627(4) 0.0271(5) Uani d . 1 . . C
  C5 0.58862(12) 0.29058(15) 0.6510(4) 0.0264(5) Uani d . 1 . . C
  C6 0.64247(12) 0.32909(15) 0.7372(4) 0.0271(5) Uani d . 1 . . C
  C7 0.56595(13) 0.45201(17) 0.1829(5) 0.0352(6) Uani d . 1 . . C
  C8 0.45121(13) 0.34002(17) 0.1606(5) 0.0385(7) Uani d . 1 . . C
  H8A 0.4434 0.3988 0.2227 0.058 Uiso calc R 1 . . H
  H8B 0.4095 0.3125 0.1231 0.058 Uiso calc R 1 . . H
  H8C 0.4780 0.3456 0.0289 0.058 Uiso calc R 1 . . H
  C9 0.55740(13) 0.21210(15) 0.7615(4) 0.0304(6) Uani d . 1 . . C
  H9A 0.5096 0.2196 0.7525 0.036 Uiso calc R 1 . . H
  H9B 0.5693 0.2142 0.9180 0.036 Uiso calc R 1 . . H
  C1' 0.57376(12) 0.12014(15) 0.6769(4) 0.0283(6) Uani d . 1 . . C
  C2' 0.60455(13) 0.10416(17) 0.4799(4) 0.0342(6) Uani d . 1 . . C
  H2' 0.6171 0.1525 0.3904 0.041 Uiso calc R 1 . . H
  C3' 0.61744(13) 0.01748(16) 0.4107(4) 0.0366(6) Uani d . 1 . . C
  H3' 0.6386 0.0071 0.2752 0.044 Uiso calc R 1 . . H
  C4' 0.59917(13) -0.05228(17) 0.5411(5) 0.0347(7) Uani d . 1 . . C
  C5' 0.56961(14) -0.03668(17) 0.7406(5) 0.0384(7) Uani d . 1 . . C
  H5' 0.5581 -0.0849 0.8322 0.046 Uiso calc R 1 . . H
  C6' 0.55706(13) 0.04777(16) 0.8057(4) 0.0338(6) Uani d . 1 . . C
  H6' 0.5364 0.0575 0.9423 0.041 Uiso calc R 1 . . H
  C1'' 0.68338(12) 0.29831(15) 0.9191(4) 0.0282(6) Uani d . 1 . . C
  C2'' 0.69774(13) 0.20879(16) 0.9466(4) 0.0323(6) Uani d . 1 . . C
  H2'' 0.6801 0.1668 0.8477 0.039 Uiso calc R 1 . . H
  C3'' 0.73697(13) 0.18032(17) 1.1144(4) 0.0347(6) Uani d . 1 . . C
  H3'' 0.7469 0.1193 1.1292 0.042 Uiso calc R 1 . . H
  C4'' 0.76191(13) 0.24062(18) 1.2614(4) 0.0343(6) Uani d . 1 . . C
  C5'' 0.74952(13) 0.33074(17) 1.2339(4) 0.0339(6) Uani d . 1 . . C
  H5'' 0.7676 0.3725 1.3325 0.041 Uiso calc R 1 . . H
  C6'' 0.71106(13) 0.35880(17) 1.0639(4) 0.0316(6) Uani d . 1 . . C
  H6'' 0.7032 0.4202 1.0446 0.038 Uiso calc R 1 . . H
  C7' 0.63684(18) -0.1613(2) 0.2865(5) 0.0534(8) Uani d . 1 . . C
  H7'1 0.6102 -0.1391 0.1658 0.080 Uiso calc R 1 . . H
  H7'2 0.6413 -0.2256 0.2740 0.080 Uiso calc R 1 . . H
  H7'3 0.6801 -0.1339 0.2807 0.080 Uiso calc R 1 . . H
  C7'' 0.80577(17) 0.12743(19) 1.4900(6) 0.0521(8) Uani d . 1 . . C
  H7''1 0.8339 0.1208 1.6183 0.078 Uiso calc R 1 . . H
  H7''2 0.8248 0.0953 1.3666 0.078 Uiso calc R 1 . . H
  H7''3 0.7625 0.1034 1.5223 0.078 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 0.0424(4) 0.0341(3) 0.0449(4) -0.0087(3) -0.0124(4) 0.0067(3)
  O1 0.0383(10) 0.0277(9) 0.0258(9) -0.0027(8) -0.0025(9) 0.0029(8)
  O2 0.0595(13) 0.0307(10) 0.0374(11) -0.0131(9) -0.0059(10) 0.0067(9)
  O3 0.0598(14) 0.0328(10) 0.0532(13) 0.0032(9) 0.0003(12) -0.0046(10)
  O4 0.0595(13) 0.0447(11) 0.0377(11) 0.0128(10) -0.0150(10) 0.0033(9)
  N1 0.0478(16) 0.0613(17) 0.0507(16) -0.0049(13) -0.0061(14) 0.0245(14)
  C2 0.0400(15) 0.0284(13) 0.0245(13) 0.0019(12) 0.0044(13) -0.0015(11)
  C3 0.0311(13) 0.0252(12) 0.0268(13) 0.0029(10) 0.0015(12) 0.0011(11)
  C4 0.0279(13) 0.0270(12) 0.0264(13) 0.0035(10) 0.0009(11) -0.0043(11)
  C5 0.0306(14) 0.0227(12) 0.0259(12) 0.0041(10) 0.0052(12) -0.0001(10)
  C6 0.0328(14) 0.0233(12) 0.0252(12) 0.0032(10) 0.0050(11) 0.0001(10)
  C7 0.0331(15) 0.0344(14) 0.0381(17) -0.0017(11) 0.0013(13) 0.0053(13)
  C8 0.0403(16) 0.0361(14) 0.0390(16) 0.0028(12) -0.0099(14) -0.0055(14)
  C9 0.0348(15) 0.0286(13) 0.0278(13) -0.0009(11) 0.0039(12) 0.0041(11)
  C1' 0.0273(13) 0.0273(13) 0.0302(14) -0.0036(10) -0.0004(12) 0.0034(11)
  C2' 0.0380(15) 0.0332(14) 0.0313(14) -0.0013(11) 0.0027(13) 0.0073(12)
  C3' 0.0398(16) 0.0385(15) 0.0315(15) -0.0011(12) 0.0032(12) -0.0044(12)
  C4' 0.0333(15) 0.0253(14) 0.0454(18) 0.0023(11) -0.0103(13) -0.0023(12)
  C5' 0.0455(17) 0.0318(14) 0.0379(16) -0.0015(13) -0.0010(14) 0.0075(13)
  C6' 0.0355(15) 0.0364(14) 0.0296(15) -0.0060(11) 0.0023(12) 0.0061(11)
  C1'' 0.0289(13) 0.0308(13) 0.0248(13) 0.0005(10) 0.0057(11) -0.0011(10)
  C2'' 0.0362(14) 0.0303(13) 0.0305(14) 0.0002(11) 0.0019(13) -0.0028(11)
  C3'' 0.0404(16) 0.0316(14) 0.0322(15) 0.0067(12) 0.0005(13) 0.0011(12)
  C4'' 0.0332(15) 0.0448(16) 0.0248(12) 0.0085(12) 0.0027(12) 0.0022(13)
  C5'' 0.0377(16) 0.0356(15) 0.0284(14) 0.0013(12) -0.0010(12) -0.0062(12)
  C6'' 0.0349(15) 0.0279(14) 0.0319(14) 0.0035(11) 0.0038(12) 0.0017(11)
  C7' 0.067(2) 0.0463(17) 0.0465(19) 0.0059(16) -0.0003(17) -0.0120(15)
  C7'' 0.062(2) 0.0511(18) 0.0437(17) 0.0143(16) -0.0066(17) 0.0152(15)
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 C4 . 1.742(2) y
  S1 C8 . 1.789(3) y
  O1 C6 . 1.372(3) ?
  O1 C2 . 1.384(3) ?
  O2 C2 . 1.204(3) ?
  O3 C4' . 1.373(3) ?
  O3 C7' . 1.425(4) ?
  O4 C4'' . 1.363(3) ?
  O4 C7'' . 1.437(3) ?
  N1 C7 . 1.149(3) ?
  C2 C3 . 1.433(3) ?
  C3 C4 . 1.378(3) ?
  C3 C7 . 1.435(4) ?
  C4 C5 . 1.448(3) ?
  C5 C6 . 1.356(3) ?
  C5 C9 . 1.510(3) ?
  C6 C1'' . 1.471(3) ?
  C9 C1' . 1.522(3) ?
  C1' C2' . 1.384(4) ?
  C1' C6' . 1.393(3) ?
  C2' C3' . 1.404(3) ?
  C3' C4' . 1.376(4) ?
  C4' C5' . 1.385(4) ?
  C5' C6' . 1.363(4) ?
  C1'' C6'' . 1.395(3) ?
  C1'' C2'' . 1.396(3) ?
  C2'' C3'' . 1.375(4) ?
  C3'' C4'' . 1.380(4) ?
  C4'' C5'' . 1.397(4) ?
  C5'' C6'' . 1.374(4) ?