#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008287.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_2008287
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_publ_section_title
;
Ethyl
1-(2-chlorophenyl)-4,6-dimethyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-
5-carboxylate
;
loop_
_publ_author_name
  'Kandasamy Chinnakali'
  'Hoong-Kun Fun'
  'Annamalai Senthilvelan'
  'Kamaraj Sriraghavan'
  'Vayalakkavoor T. Ramakrishnan'
_chemical_formula_sum  'C15 H17 Cl N2 O2 S'
_chemical_formula_iupac  'C15 H17 Cl N2 O2 S'
_chemical_formula_weight  324.82
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, -y, -z'
  'x-1/2, y, -z-1/2'
  'x, -y-1/2, z-1/2'
  '-x-1/2, y-1/2, z'
_cell_length_a  7.5623(2)
_cell_length_b  19.8757(6)
_cell_length_c  21.2828(6)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  3198.9(2)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.349
_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
  Cl1 0.21133(11) 0.21111(4) 0.61309(5) 0.0626(3) Uani d . 1 . . Cl
  S1 0.20989(10) 0.08295(3) 0.49226(3) 0.0442(2) Uani d . 1 . . S
  O1 0.3158(4) -0.01744(13) 0.79565(10) 0.0711(7) Uani d . 1 . . O
  O2 0.2195(3) -0.10732(11) 0.74309(9) 0.0552(5) Uani d . 1 . . O
  N1 0.3545(3) 0.07022(10) 0.60744(10) 0.0367(5) Uani d . 1 . . N
  N2 0.1363(3) -0.00423(11) 0.58205(10) 0.0449(6) Uani d . 1 . . N
  H2 0.0343 -0.0102 0.5650 0.054 Uiso calc R 1 . . H
  C1 0.3553(3) 0.04629(12) 0.67072(11) 0.0378(5) Uani d . 1 . . C
  C2 0.2746(3) -0.01223(13) 0.68340(11) 0.0378(5) Uani d . 1 . . C
  C3 0.1949(4) -0.05186(14) 0.63015(12) 0.0417(6) Uani d . 1 . . C
  H3 0.0914 -0.0762 0.6460 0.050 Uiso calc R 1 . . H
  C4 0.2330(3) 0.04766(12) 0.56354(11) 0.0349(5) Uani d . 1 . . C
  C5 0.4751(3) 0.12302(12) 0.58987(11) 0.0362(5) Uani d . 1 . . C
  C6 0.4230(4) 0.19026(13) 0.59031(13) 0.0432(6) Uani d . 1 . . C
  C7 0.5400(5) 0.24058(15) 0.57318(14) 0.0552(8) Uani d . 1 . . C
  H7 0.5033 0.2852 0.5723 0.066 Uiso calc R 1 . . H
  C8 0.7110(5) 0.22406(18) 0.55743(14) 0.0594(9) Uani d . 1 . . C
  H8 0.7902 0.2577 0.5459 0.071 Uiso calc R 1 . . H
  C9 0.7653(4) 0.1580(2) 0.55863(15) 0.0605(9) Uani d . 1 . . C
  H9 0.8817 0.1473 0.5487 0.073 Uiso calc R 1 . . H
  C10 0.6476(4) 0.10729(16) 0.57446(14) 0.0489(7) Uani d . 1 . . C
  H10 0.6848 0.0627 0.5747 0.059 Uiso calc R 1 . . H
  C11 0.4496(4) 0.09116(15) 0.71707(13) 0.0522(7) Uani d . 1 . . C
  H11A 0.4335 0.0739 0.7588 0.078 Uiso calc R 1 . . H
  H11B 0.4018 0.1358 0.7146 0.078 Uiso calc R 1 . . H
  H11C 0.5735 0.0923 0.7073 0.078 Uiso calc R 1 . . H
  C12 0.2725(4) -0.04264(14) 0.74662(13) 0.0441(6) Uani d . 1 . . C
  C13 0.2293(5) -0.14650(18) 0.80027(14) 0.0583(8) Uani d . 1 . . C
  H13A 0.1636 -0.1246 0.8336 0.070 Uiso calc R 1 . . H
  H13B 0.3513 -0.1513 0.8136 0.070 Uiso calc R 1 . . H
  C14 0.1509(6) -0.21401(19) 0.78613(17) 0.0737(11) Uani d . 1 . . C
  H14A 0.1695 -0.2435 0.8212 0.111 Uiso calc R 1 . . H
  H14B 0.2065 -0.2325 0.7495 0.111 Uiso calc R 1 . . H
  H14C 0.0263 -0.2092 0.7787 0.111 Uiso calc R 1 . . H
  C15 0.3215(5) -0.10232(15) 0.60134(14) 0.0587(8) Uani d . 1 . . C
  H15A 0.2643 -0.1250 0.5671 0.088 Uiso calc R 1 . . H
  H15B 0.3557 -0.1347 0.6326 0.088 Uiso calc R 1 . . H
  H15C 0.4246 -0.0793 0.5862 0.088 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
  Cl1 0.0503(4) 0.0489(4) 0.0886(6) 0.0125(3) -0.0035(4) -0.0124(4)
  S1 0.0480(4) 0.0428(4) 0.0416(3) -0.0084(3) -0.0121(3) 0.0080(3)
  O1 0.109(2) 0.0660(15) 0.0383(11) -0.0077(14) -0.0114(12) 0.0008(10)
  O2 0.0717(14) 0.0554(11) 0.0386(10) -0.0130(11) -0.0054(10) 0.0133(9)
  N1 0.0371(11) 0.0344(10) 0.0386(10) -0.0040(8) -0.0076(9) 0.0019(8)
  N2 0.0414(12) 0.0480(13) 0.0453(12) -0.0149(10) -0.0166(10) 0.0100(10)
  C1 0.0367(12) 0.0383(13) 0.0383(12) 0.0017(10) -0.0077(10) -0.0019(10)
  C2 0.0367(13) 0.0422(13) 0.0346(12) -0.0014(11) -0.0027(10) 0.0011(10)
  C3 0.0444(14) 0.0437(14) 0.0371(12) -0.0131(11) -0.0069(11) 0.0079(10)
  C4 0.0304(12) 0.0343(12) 0.0399(12) -0.0002(9) -0.0060(10) -0.0001(10)
  C5 0.0333(12) 0.0359(12) 0.0394(12) -0.0038(10) -0.0048(10) -0.0031(10)
  C6 0.0419(14) 0.0398(13) 0.0481(14) -0.0029(11) -0.0059(12) -0.0035(11)
  C7 0.068(2) 0.0422(15) 0.0557(17) -0.0149(14) -0.0140(15) 0.0016(13)
  C8 0.062(2) 0.067(2) 0.0495(16) -0.0318(17) -0.0022(15) -0.0009(15)
  C9 0.0382(15) 0.091(3) 0.0529(17) -0.0165(16) 0.0044(13) -0.0150(17)
  C10 0.0386(14) 0.0534(16) 0.0546(16) -0.0016(13) -0.0038(12) -0.0107(13)
  C11 0.0632(19) 0.0483(15) 0.0452(15) -0.0085(14) -0.0160(14) -0.0040(12)
  C12 0.0434(14) 0.0511(15) 0.0378(12) 0.0013(12) -0.0004(11) 0.0043(12)
  C13 0.067(2) 0.068(2) 0.0403(14) -0.0039(16) 0.0006(14) 0.0170(14)
  C14 0.077(2) 0.075(2) 0.069(2) -0.024(2) -0.0117(19) 0.0320(18)
  C15 0.087(2) 0.0408(15) 0.0478(16) -0.0001(16) -0.0067(16) -0.0023(12)
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
  Cl1 C6 . 1.723(3) ?
  S1 C4 . 1.680(2) yes
  O1 C12 . 1.203(3) yes
  O2 C12 . 1.349(3) yes
  O2 C13 . 1.447(3) yes
  N1 C4 . 1.385(3) yes
  N1 C1 . 1.428(3) yes
  N1 C5 . 1.440(3) yes
  N2 C4 . 1.324(3) yes
  N2 C3 . 1.463(3) yes
  N2 H2 . 0.8600 ?
  C1 C2 . 1.341(4) yes
  C1 C11 . 1.509(3) ?
  C2 C12 . 1.475(4) yes
  C2 C3 . 1.506(4) yes
  C3 C15 . 1.516(4) ?
  C3 H3 . 0.9800 ?
  C5 C10 . 1.380(4) ?
  C5 C6 . 1.393(4) ?
  C6 C7 . 1.384(4) ?
  C7 C8 . 1.375(5) ?
  C7 H7 . 0.9300 ?
  C8 C9 . 1.376(5) ?
  C8 H8 . 0.9300 ?
  C9 C10 . 1.386(4) ?
  C9 H9 . 0.9300 ?
  C10 H10 . 0.9300 ?
  C11 H11A . 0.9600 ?
  C11 H11B . 0.9600 ?
  C11 H11C . 0.9600 ?
  C13 C14 . 1.497(5) ?
  C13 H13A . 0.9700 ?
  C13 H13B . 0.9700 ?
  C14 H14A . 0.9600 ?
  C14 H14B . 0.9600 ?
  C14 H14C . 0.9600 ?
  C15 H15A . 0.9600 ?
  C15 H15B . 0.9600 ?
  C15 H15C . 0.9600 ?