#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012859.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_2012859
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o496
_journal_page_last  o498
_publ_section_title
;
2-(4-Benzenesulfonylmethyl-2-methyl-5-nitroimidazol-1-yl)ethanol
and 4-benzenesulfonylmethyl-2-methyl-5-nitrothiazole
;
_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
  'Crozet, M. D.'
  'Vanelle, P.'
  'Giorgi, M.'
  'Gellis, A.'
_chemical_formula_moiety  'C13 H15 N3 O5 S1'
_chemical_formula_sum  'C13 H15 N3 O5 S1'
_chemical_formula_structural  'C13 H15 N3 O5 S'
_chemical_formula_iupac  'C13 H15 N3 O5 S1'
_chemical_formula_weight  325.343
_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  12.5976(3)
_cell_length_b  7.7874(3)
_cell_length_c  14.8929(5)
_cell_angle_alpha  90.
_cell_angle_beta  94.427(2)
_cell_angle_gamma  90.
_cell_volume  1456.67(8)
_cell_formula_units_Z  4
_cell_measurement_temperature  293
_exptl_crystal_density_diffrn  1.484
_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
  S1 0.21423(4) 0.02005(6) 0.10308(3) 0.05482(19) Uani d . 1 . . S
  O1 0.14467(15) -0.10385(19) 0.05876(12) 0.0865(6) Uani d . 1 . . O
  O2 0.32604(12) -0.0151(2) 0.11349(11) 0.0763(5) Uani d . 1 . . O
  O3 0.15023(17) 0.6036(2) 0.28117(17) 0.1074(7) Uani d . 1 . . O
  O4 0.06922(12) 0.3935(2) 0.21328(12) 0.0743(5) Uani d . 1 . . O
  O5 0.45589(12) 0.80584(17) 0.33634(13) 0.0762(5) Uani d . 1 . . O
  H5B 0.4093 0.8795 0.3350 0.114 Uiso calc R 1 . . H
  N1 0.32903(10) 0.10909(16) 0.31418(9) 0.0388(3) Uani d . 1 . . N
  N2 0.31723(11) 0.38808(16) 0.34262(8) 0.0392(3) Uani d . 1 . . N
  N3 0.14515(13) 0.4535(2) 0.25888(11) 0.0540(4) Uani d . 1 . . N
  C1 0.19509(13) 0.2181(2) 0.04813(11) 0.0461(4) Uani d . 1 . . C
  C2 0.10579(15) 0.2396(3) -0.01101(12) 0.0520(4) Uani d . 1 . . C
  H2 0.0578 0.1499 -0.0221 0.062 Uiso calc R 1 . . H
  C3 0.08906(17) 0.3957(3) -0.05324(13) 0.0602(5) Uani d . 1 . . C
  H3 0.0304 0.4108 -0.0943 0.072 Uiso calc R 1 . . H
  C4 0.15864(19) 0.5290(3) -0.03497(15) 0.0656(6) Uani d . 1 . . C
  H4 0.1457 0.6349 -0.0626 0.079 Uiso calc R 1 . . H
  C5 0.24722(18) 0.5075(3) 0.02373(15) 0.0634(5) Uani d . 1 . . C
  H5 0.2936 0.5990 0.0357 0.076 Uiso calc R 1 . . H
  C6 0.26790(14) 0.3511(3) 0.06516(12) 0.0527(4) Uani d . 1 . . C
  H6 0.3289 0.3349 0.1035 0.063 Uiso calc R 1 . . H
  C7 0.16892(14) 0.0505(2) 0.21300(13) 0.0491(4) Uani d . 1 . . C
  H7A 0.0972 0.0966 0.2071 0.059 Uiso calc R 1 . . H
  H7B 0.1663 -0.0600 0.2429 0.059 Uiso calc R 1 . . H
  C8 0.23837(12) 0.1683(2) 0.26970(10) 0.0374(3) Uani d . 1 . . C
  C9 0.37456(12) 0.2425(2) 0.35730(10) 0.0377(3) Uani d . 1 . . C
  C10 0.22990(12) 0.3413(2) 0.28604(10) 0.0386(3) Uani d . 1 . . C
  C11 0.47418(15) 0.2306(2) 0.41651(12) 0.0519(4) Uani d . 1 . . C
  H11A 0.5009 0.1152 0.4158 0.078 Uiso calc R 1 . . H
  H11B 0.4601 0.2613 0.4769 0.078 Uiso calc R 1 . . H
  H11C 0.5262 0.3077 0.3952 0.078 Uiso calc R 1 . . H
  C12 0.35328(16) 0.5592(2) 0.37392(12) 0.0510(4) Uani d . 1 . . C
  H12A 0.3999 0.5475 0.4285 0.061 Uiso calc R 1 . . H
  H12B 0.2922 0.6273 0.3879 0.061 Uiso calc R 1 . . H
  C13 0.41195(17) 0.6501(2) 0.30297(14) 0.0555(5) Uani d . 1 . . C
  H13A 0.4684 0.5766 0.2843 0.067 Uiso calc R 1 . . H
  H13B 0.3632 0.6729 0.2507 0.067 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 0.0532(3) 0.0423(3) 0.0657(3) 0.01013(18) -0.0171(2) -0.01797(19)
  O1 0.1042(13) 0.0465(8) 0.1007(12) -0.0015(8) -0.0432(10) -0.0254(8)
  O2 0.0625(9) 0.0831(11) 0.0809(10) 0.0370(8) -0.0100(7) -0.0232(8)
  O3 0.1008(14) 0.0509(10) 0.164(2) 0.0333(9) -0.0323(13) -0.0187(11)
  O4 0.0509(8) 0.0752(10) 0.0934(11) 0.0187(7) -0.0154(7) 0.0023(8)
  O5 0.0624(9) 0.0306(6) 0.1301(14) -0.0031(6) -0.0278(9) 0.0022(7)
  N1 0.0364(7) 0.0323(6) 0.0470(7) -0.0025(5) -0.0023(5) 0.0057(5)
  N2 0.0457(7) 0.0336(7) 0.0384(6) -0.0020(5) 0.0035(5) -0.0010(5)
  N3 0.0510(9) 0.0498(9) 0.0612(9) 0.0154(7) 0.0040(7) 0.0040(7)
  C1 0.0408(9) 0.0523(10) 0.0450(8) 0.0059(7) 0.0017(7) -0.0127(7)
  C2 0.0446(9) 0.0609(11) 0.0495(9) 0.0043(8) -0.0036(7) -0.0098(8)
  C3 0.0574(11) 0.0756(14) 0.0474(10) 0.0159(10) 0.0036(8) 0.0003(9)
  C4 0.0770(15) 0.0629(13) 0.0592(11) 0.0081(11) 0.0192(10) 0.0068(9)
  C5 0.0643(13) 0.0629(12) 0.0648(12) -0.0115(10) 0.0172(10) -0.0032(10)
  C6 0.0430(9) 0.0652(12) 0.0504(9) -0.0016(8) 0.0061(7) -0.0118(8)
  C7 0.0393(9) 0.0403(9) 0.0656(11) -0.0074(7) -0.0087(7) 0.0054(8)
  C8 0.0340(7) 0.0356(8) 0.0424(8) -0.0026(6) 0.0016(6) 0.0061(6)
  C9 0.0383(8) 0.0350(7) 0.0395(7) -0.0043(6) 0.0015(6) 0.0049(6)
  C10 0.0386(8) 0.0376(8) 0.0398(7) 0.0042(6) 0.0042(6) 0.0033(6)
  C11 0.0452(9) 0.0515(10) 0.0567(10) -0.0084(8) -0.0106(8) 0.0038(8)
  C12 0.0676(12) 0.0363(8) 0.0486(9) -0.0016(8) 0.0010(8) -0.0105(7)
  C13 0.0646(12) 0.0317(8) 0.0695(12) -0.0049(8) 0.0005(9) 0.0020(8)
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 O1 . 1.4300(15) y
  S1 O2 . 1.4314(15) y
  S1 C1 . 1.7537(19) y
  S1 C7 . 1.791(2) y
  O3 N3 . 1.215(2) ?
  O4 N3 . 1.222(2) ?
  O5 C13 . 1.408(2) y
  O5 H5B . 0.8200 ?
  N1 C9 . 1.328(2) y
  N1 C8 . 1.3562(19) y
  N2 C9 . 1.353(2) y
  N2 C10 . 1.382(2) y
  N2 C12 . 1.472(2) y
  N3 C10 . 1.415(2) ?
  C1 C2 . 1.384(2) ?
  C1 C6 . 1.394(3) ?
  C2 C3 . 1.377(3) ?
  C2 H2 . 0.9300 ?
  C3 C4 . 1.373(3) ?
  C3 H3 . 0.9300 ?
  C4 C5 . 1.374(3) ?
  C4 H4 . 0.9300 ?
  C5 C6 . 1.381(3) ?
  C5 H5 . 0.9300 ?
  C6 H6 . 0.9300 ?
  C7 C8 . 1.486(2) ?
  C7 H7A . 0.9700 ?
  C7 H7B . 0.9700 ?
  C8 C10 . 1.374(2) y
  C9 C11 . 1.480(2) ?
  C11 H11A . 0.9600 ?
  C11 H11B . 0.9600 ?
  C11 H11C . 0.9600 ?
  C12 C13 . 1.511(3) y
  C12 H12A . 0.9700 ?
  C12 H12B . 0.9700 ?
  C13 H13A . 0.9700 ?
  C13 H13B . 0.9700 ?