#------------------------------------------------------------------------------
#$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: svn://www.crystallography.net/cod/cif/2/2010197.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_2010197
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1994
_journal_volume 50
_journal_page_first  1825
_journal_page_last  1828
_publ_section_title
;
3-Chloro- and 3-Bromo-2-oxopropyl p-Toluenesulfonates
;
loop_
_publ_author_name
  'Howard, Judith A.K.'
  'Batsanov, Andrei S.'
  "O'Hagan, David"
  'White, Jeffrey'
_chemical_name_common  '3-Bromo-2-oxopropyltosylate'
_chemical_formula_sum  'C10 H11 Br1 O4 S1'
_chemical_formula_analytical  'C39.3%, H3.6%'
_chemical_formula_weight  307.16
_chemical_melting_point  67.0
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
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  11.002(2)
_cell_length_b  5.160(2)
_cell_length_c  22.490(3)
_cell_angle_alpha  90.00
_cell_angle_beta  110.48(3)
_cell_angle_gamma  90.00
_cell_volume  1196.3(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.706
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  0.0401
_refine_ls_wR_factor_obs  0.0877
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  Br 0.16417(5) 0.19840(11) 0.01966(2) 0.0619(2) Uani d . 1 . Br
  S 0.21392(9) 0.9838(2) 0.23277(5) 0.0327(2) Uani d . 1 . S
  O1 0.1776(2) 0.8066(5) 0.17120(11) 0.0351(6) Uani d . 1 . O
  O2 0.2994(3) 1.1711(5) 0.22244(13) 0.0425(7) Uani d . 1 . O
  O3 0.0971(3) 1.0660(6) 0.24121(13) 0.0418(7) Uani d . 1 . O
  O4 -0.0184(3) 0.2805(6) 0.09153(15) 0.0559(9) Uani d . 1 . O
  C1 0.2986(3) 0.7725(7) 0.2942(2) 0.0306(9) Uani d . 1 . C
  C2 0.4257(4) 0.7088(8) 0.3032(2) 0.0364(9) Uani d . 1 . C
  H2 0.4675(4) 0.7827(8) 0.2779(2) 0.044 Uiso calc R 1 . H
  C3 0.4901(4) 0.5343(9) 0.3502(2) 0.0420(10) Uani d . 1 . C
  H3 0.5754(4) 0.4893(9) 0.3561(2) 0.050 Uiso calc R 1 . H
  C4 0.4289(4) 0.4246(9) 0.3889(2) 0.0418(10) Uani d . 1 . C
  C5 0.3028(4) 0.4939(10) 0.3798(2) 0.0512(12) Uani d . 1 . C
  H5 0.2618(4) 0.4235(10) 0.4058(2) 0.061 Uiso calc R 1 . H
  C6 0.2356(4) 0.6669(9) 0.3323(2) 0.0450(11) Uani d . 1 . C
  H6 0.1502(4) 0.7111(9) 0.3262(2) 0.054 Uiso calc R 1 . H
  C7 0.4994(5) 0.2299(10) 0.4393(2) 0.0639(14) Uani d . 1 . C
  H7A 0.5883(10) 0.282(4)  0.4590(11) 0.102(12) Uiso calc R 1 . H
  H7B 0.496(3)  0.0624(16) 0.4202(4) 0.102(12) Uiso calc R 1 . H
  H7C 0.459(2)  0.222(5)  0.4708(9) 0.102(12) Uiso calc R 1 . H
  C8 0.0665(4) 0.6369(8) 0.1575(2) 0.0404(10) Uani d . 1 . C
  H8A -0.0126(4) 0.7385(8) 0.1427(2) 0.067(11) Uiso calc R 1 . H
  H8B 0.0695(4) 0.5470(8) 0.1959(2) 0.067(11) Uiso calc R 1 . H
  C9 0.0660(4) 0.4416(8) 0.1073(2) 0.0370(10) Uani d . 1 . C
  C10 0.1735(4) 0.4637(8) 0.0809(2) 0.0435(11) Uani d . 1 . C
  H10A 0.2563(4) 0.4518(8) 0.1154(2) 0.049(9) Uiso calc R 1 . H
  H10B 0.1690(4) 0.6322(8) 0.0611(2) 0.049(9) 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
  Br 0.0868(4) 0.0567(3) 0.0447(3) 0.0080(3) 0.0263(3) -0.0059(3)
  S 0.0355(5) 0.0305(5) 0.0339(5) 0.0014(5) 0.0144(4) -0.0001(4)
  O1 0.0387(15) 0.038(2) 0.0302(13) -0.0065(13) 0.0141(12) -0.0050(13)
  O2 0.049(2) 0.033(2) 0.048(2) -0.0068(14) 0.0205(14) 0.0020(14)
  O3 0.042(2) 0.042(2) 0.043(2) 0.0100(14) 0.0170(13) 0.0009(14)
  O4 0.059(2) 0.055(2) 0.054(2) -0.018(2) 0.021(2) -0.012(2)
  C1 0.032(2) 0.033(2) 0.027(2) -0.001(2) 0.011(2) -0.003(2)
  C2 0.034(2) 0.041(2) 0.037(2) 0.001(2) 0.016(2) 0.002(2)
  C3 0.032(2) 0.049(3) 0.043(2) 0.007(2) 0.011(2) 0.001(2)
  C4 0.051(3) 0.039(2) 0.032(2) 0.004(2) 0.010(2) 0.002(2)
  C5 0.054(3) 0.065(3) 0.040(2) -0.001(3) 0.022(2) 0.011(2)
  C6 0.037(2) 0.061(3) 0.042(2) 0.004(2) 0.019(2) 0.006(2)
  C7 0.073(3) 0.063(4) 0.051(3) 0.016(3) 0.017(3) 0.017(3)
  C8 0.037(2) 0.040(3) 0.043(2) -0.002(2) 0.013(2) -0.008(2)
  C9 0.041(2) 0.036(2) 0.031(2) 0.000(2) 0.009(2) 0.003(2)
  C10 0.056(3) 0.036(3) 0.040(2) -0.002(2) 0.018(2) -0.004(2)
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
  Br C10 . 1.920(4) yes
  S O2 . 1.424(3) yes
  S O3 . 1.428(3) yes
  S O1 . 1.590(3) yes
  S C1 . 1.750(4) yes
  O1 C8 . 1.447(5) yes
  O4 C9 . 1.204(5) yes
  C1 C2 . 1.381(5) ?
  C1 C6 . 1.389(5) ?
  C2 C3 . 1.381(6) ?
  C3 C4 . 1.394(6) ?
  C4 C5 . 1.377(6) ?
  C4 C7 . 1.510(6) ?
  C5 C6 . 1.389(6) ?
  C8 C9 . 1.512(5) yes
  C9 C10 . 1.501(5) yes