#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2200679.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_2200679
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o976
_journal_page_last  o977
_publ_section_title
;
2-Ethyl 5-methyl 3-hydroxythiophene-2,5-dicarboxylate
;
loop_
_publ_author_name
  'Coles, Simon J.'
  'Guthmann, Holger'
  'Hursthouse, Michael B.'
  'Murphy, Patrick J.'
_chemical_formula_moiety  'C9 H10 O5 S'
_chemical_formula_sum  'C9 H10 O5 S'
_chemical_formula_iupac  'C9 H10 O5 S'
_chemical_formula_weight  230.23
_symmetry_cell_setting  Triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  7.6602(15)
_cell_length_b  11.120(2)
_cell_length_c  12.572(3)
_cell_angle_alpha  94.09(3)
_cell_angle_beta  102.64(3)
_cell_angle_gamma  95.77(3)
_cell_volume  1034.8(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.478
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
  C1  .1020(6)  .8616(4)  .1125(3)  .0173(9) Uani d . 1 . . C
  C2  .0445(6)  .7823(4)  .0168(3)  .0182(9) Uani d . 1 . . C
  C3  -.0531(6)  .6743(4)  .0314(3)  .0179(9) Uani d . 1 . . C
  H3  -.1037  .6112  -.0252  .021 Uiso calc R 1 . . H
  C4  -.0665(6)  .6711(4)  .1389(3)  .0173(9) Uani d . 1 . . C
  C5  .2018(6)  .9802(4)  .1200(4)  .0196(9) Uani d . 1 . . C
  C6  .3425(7) 1.1587(4)  .2326(4)  .0250(10) Uani d . 1 . . C
  H6A  .2659 1.2176  .1966  .03 Uiso calc R 1 . . H
  H6B  .4478 1.1559  .1992  .03 Uiso calc R 1 . . H
  C7  .4038(7) 1.1955(5)  .3553(4)  .0288(11) Uani d . 1 . . C
  H7A  .2982 1.2009  .3866  .043 Uiso calc R 1 . . H
  H7B  .4778 1.2746  .368  .043 Uiso calc R 1 . . H
  H7C  .475 1.1345  .3901  .043 Uiso calc R 1 . . H
  C8  -.1540(6)  .5754(4)  .1913(4)  .0213(9) Uani d . 1 . . C
  C9  -.3363(9)  .3880(5)  .1654(5)  .0362(13) Uani d . 1 . . C
  H9A  -.2455  .3496  .2148  .054 Uiso calc R 1 . . H
  H9B  -.405  .3274  .1069  .054 Uiso calc R 1 . . H
  H9C  -.4182  .4213  .2065  .054 Uiso calc R 1 . . H
  C10  .4102(6) 1.1500(4)  -.2462(3)  .0177(9) Uani d . 1 . . C
  C11  .4792(6) 1.2216(4)  -.1474(4)  .0200(9) Uani d . 1 . . C
  C12  .5760(6) 1.3324(4)  -.1600(4)  .0189(9) Uani d . 1 . . C
  H12  .6314 1.3925  -.1015  .023 Uiso calc R 1 . . H
  C13  .5797(6) 1.3420(4)  -.2679(4)  .0193(9) Uani d . 1 . . C
  C14  .3042(6) 1.0322(4)  -.2554(4)  .0184(9) Uani d . 1 . . C
  C15  .1275(7)  .8674(5)  -.3723(4)  .0281(11) Uani d . 1 . . C
  H15A  .0185  .8762  -.3436  .034 Uiso calc R 1 . . H
  H15B  .1958  .8078  -.3312  .034 Uiso calc R 1 . . H
  C16  .0748(7)  .8243(5)  -.4930(4)  .0268(10) Uani d . 1 . . C
  H16A  .0043  .8827  -.5327  .04 Uiso calc R 1 . . H
  H16B  .0022  .7448  -.5038  .04 Uiso calc R 1 . . H
  H16C  .1836  .8174  -.5209  .04 Uiso calc R 1 . . H
  C17  .6773(6) 1.4418(4)  -.3094(4)  .0205(9) Uani d . 1 . . C
  C18  .7694(7) 1.5099(5)  -.4642(4)  .0287(11) Uani d . 1 . . C
  H18A  .7183 1.587  -.4598  .043 Uiso calc R 1 . . H
  H18B  .7622 1.4826  -.541  .043 Uiso calc R 1 . . H
  H18C  .8958 1.5214  -.424  .043 Uiso calc R 1 . . H
  O1  .2456(5) 1.0210(3)  .0414(3)  .0259(8) Uani d . 1 . . O
  O2  .2403(5) 1.0387(3)  .2207(3)  .0232(7) Uani d . 1 . . O
  O3  .0755(5)  .8058(3)  -.0820(2)  .0217(7) Uani d . 1 . . O
  H3A  .1326  .8753  -.0769  .033 Uiso calc R 1 . . H
  O4  -.1432(5)  .5783(3)  .2892(3)  .0247(7) Uani d . 1 . . O
  O5  -.2478(5)  .4852(3)  .1179(3)  .0247(7) Uani d . 1 . . O
  O6  .2804(5)  .9828(3)  -.1758(3)  .0266(8) Uani d . 1 . . O
  O7  .2387(4)  .9840(3)  -.3593(2)  .0212(7) Uani d . 1 . . O
  O8  .4581(5) 1.1940(3)  -.0480(3)  .0249(7) Uani d . 1 . . O
  H8  .3961 1.126  -.0541  .037 Uiso calc R 1 . . H
  O9  .7556(5) 1.5338(3)  -.2526(3)  .0296(8) Uani d . 1 . . O
  O10  .6700(5) 1.4204(3)  -.4169(3)  .0247(7) Uani d . 1 . . O
  S1  .03654(14)  .79934(10)  .22139(8)  .0179(3) Uani d . 1 . . S
  S2  .46669(15) 1.21826(10)  -.35415(9)  .0192(3) Uani d . 1 . . S
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
  C1  .022(2)  .018(2)  .0128(19)  .0020(16)  .0061(16)  .0016(16)
  C2  .020(2)  .022(2)  .0127(19)  .0031(17)  .0043(16)  .0024(16)
  C3  .016(2)  .022(2)  .015(2)  .0003(16)  .0030(15)  .0030(16)
  C4  .017(2)  .021(2)  .0162(19)  .0035(16)  .0058(15)  .0067(16)
  C5  .022(2)  .024(2)  .015(2)  .0050(17)  .0082(17)  .0019(17)
  C6  .030(2)  .020(2)  .023(2)  -.0005(18)  .0021(19)  .0019(18)
  C7  .031(3)  .035(3)  .023(2)  .009(2)  .011(2)  -.001(2)
  C8  .019(2)  .022(2)  .022(2)  -.0014(17)  .0055(17)  .0014(18)
  C9  .057(4)  .022(3)  .033(3)  -.010(2)  .025(3)  .002(2)
  C10  .021(2)  .020(2)  .0140(19)  .0025(17)  .0061(16)  .0045(16)
  C11  .021(2)  .024(2)  .016(2)  .0057(17)  .0045(16)  .0065(17)
  C12  .018(2)  .019(2)  .020(2)  .0020(16)  .0051(16)  .0013(17)
  C13  .020(2)  .017(2)  .022(2)  .0028(16)  .0062(17)  .0008(17)
  C14  .016(2)  .023(2)  .016(2)  -.0001(16)  .0059(16)  .0004(17)
  C15  .034(3)  .025(2)  .023(2)  -.010(2)  .007(2)  .0014(19)
  C16  .030(3)  .032(3)  .016(2)  .004(2)  -.0002(18)  -.0015(19)
  C17  .018(2)  .023(2)  .022(2)  .0042(17)  .0081(17)  .0046(18)
  C18  .031(3)  .028(3)  .031(3)  .002(2)  .014(2)  .008(2)
  O1  .0350(19)  .0261(18)  .0184(16)  -.0022(14)  .0125(14)  .0022(13)
  O2  .0281(17)  .0228(17)  .0187(16)  .0003(13)  .0065(13)  .0018(13)
  O3  .0272(17)  .0230(17)  .0144(15)  -.0027(13)  .0056(12)  .0026(12)
  O4  .0312(18)  .0253(18)  .0187(16)  -.0008(14)  .0088(13)  .0051(13)
  O5  .0353(19)  .0210(17)  .0183(16)  -.0067(14)  .0127(14)  -.0007(13)
  O6  .0335(19)  .0273(18)  .0181(16)  -.0041(14)  .0079(14)  .0012(14)
  O7  .0227(16)  .0242(17)  .0152(15)  -.0031(13)  .0034(12)  .0026(12)
  O8  .0329(18)  .0270(18)  .0144(15)  -.0048(14)  .0082(13)  .0025(13)
  O9  .035(2)  .0220(18)  .0336(19)  -.0047(14)  .0157(16)  -.0015(15)
  O10  .0290(18)  .0246(17)  .0218(16)  -.0026(13)  .0100(14)  .0062(13)
  S1  .0195(6)  .0206(6)  .0142(5)  .0018(4)  .0055(4)  .0017(4)
  S2  .0202(6)  .0225(6)  .0151(5)  -.0009(4)  .0056(4)  .0032(4)
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
  C1 C2 . 1.399(6) ?
  C1 C5 . 1.442(6) ?
  C1 S1 . 1.724(4) ?
  C2 O3 . 1.353(5) ?
  C2 C3 . 1.395(6) ?
  C3 C4 . 1.380(6) ?
  C3 H3 .  .95 ?
  C4 C8 . 1.471(6) ?
  C4 S1 . 1.714(5) ?
  C5 O1 . 1.213(6) ?
  C5 O2 . 1.339(5) ?
  C6 O2 . 1.459(6) ?
  C6 C7 . 1.523(7) ?
  C6 H6A .  .99 ?
  C6 H6B .  .99 ?
  C7 H7A .  .98 ?
  C7 H7B .  .98 ?
  C7 H7C .  .98 ?
  C8 O4 . 1.214(6) ?
  C8 O5 . 1.344(6) ?
  C9 O5 . 1.451(6) ?
  C9 H9A .  .98 ?
  C9 H9B .  .98 ?
  C9 H9C .  .98 ?
  C10 C11 . 1.394(6) ?
  C10 C14 . 1.453(6) ?
  C10 S2 . 1.716(4) ?
  C11 O8 . 1.348(5) ?
  C11 C12 . 1.410(6) ?
  C12 C13 . 1.375(6) ?
  C12 H12 .  .95 ?
  C13 C17 . 1.466(6) ?
  C13 S2 . 1.719(5) ?
  C14 O6 . 1.214(6) ?
  C14 O7 . 1.343(5) ?
  C15 O7 . 1.456(6) ?
  C15 C16 . 1.512(6) ?
  C15 H15A .  .99 ?
  C15 H15B .  .99 ?
  C16 H16A .  .98 ?
  C16 H16B .  .98 ?
  C16 H16C .  .98 ?
  C17 O9 . 1.225(6) ?
  C17 O10 . 1.343(6) ?
  C18 O10 . 1.433(6) ?
  C18 H18A .  .98 ?
  C18 H18B .  .98 ?
  C18 H18C .  .98 ?
  O3 H3A .  .84 ?
  O8 H8 .  .84 ?