#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011323.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_2011323
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  1164
_journal_page_last  1167
_publ_section_title
;
From \a-carbamoyl-\a-cyanooxiranes to 3-halogenopyruvamides;
3-(4-chlorophenyl)-2-cyano-2,3-epoxypropanamide,
3-bromo-2-cyano-2-hydroxy-3-(m-tolyl)propanamide,
3-bromo-2-oxo-3-(m-tolyl)propanamide and
3-chloro-2,2-dihydroxy-3-phenylpropanamide
;
_space_group_IT_number           9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_[local]_cod_cif_authors_sg_H-M  'C c'
loop_
_publ_author_name
  'Lah, Nina'
  'Leban, Ivan'
  "Majcen-Le Mar\'echal, Alenka"
  'Le Grel, Philippe'
  'Robert, Albert'
  'Sieler, Joachim'
  'Giester, Gerald'
_chemical_formula_moiety  'C9 H10 Cl N O3'
_chemical_formula_sum  'C9 H10 Cl N O3'
_chemical_formula_weight  215.63
_symmetry_cell_setting  monoclinic
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  5.5260(10)
_cell_length_b  29.989(6)
_cell_length_c  5.9970(10)
_cell_angle_alpha  90.00
_cell_angle_beta  107.96(3)
_cell_angle_gamma  90.00
_cell_volume  945.4(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.515
_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
  Cl  .16258(8)  .124077(19)  .21761(8)  .05386(18) Uani d . 1 . . Cl
  O2  -.3113(2)  .06060(5)  .03079(18)  .0496(4) Uani d . 1 . . O
  H21  -.2398  .0616  .1725  .073(9) Uiso calc R 1 . . H
  O1  -.1405(2)  .05041(5)  -.48339(19)  .0561(4) Uani d R 1 . . O
  C4  -.2056(4)  .14729(6)  -.1812(3)  .0384(4) Uani d . 1 . . C
  O3  .0723(3)  .03416(5)  .0011(3)  .0550(4) Uani d . 1 . . O
  H31  .0174  .0087  -.0038  .106(13) Uiso calc R 1 . . H
  N1  -.5146(4)  .04729(7)  -.4077(4)  .0606(5) Uani d . 1 . . N
  H1  -.5987  .0412  -.5508  .091(10) Uiso calc R 1 . . H
  H2  -.5925  .0496  -.3042  .069(8) Uiso calc R 1 . . H
  C3  -.0171(4)  .11083(6)  -.0800(3)  .0386(5) Uani d . 1 . . C
  H3  .1032  .1099  -.1714  .052(6) Uiso calc R 1 . . H
  C2  -.1314(4)  .06384(7)  -.0872(3)  .0391(4) Uani d . 1 . . C
  C9  -.2038(4)  .16836(7)  -.3868(4)  .0468(5) Uani d . 1 . . C
  H9  -.0877  .1595  -.4622  .047(6) Uiso calc R 1 . . H
  C5  -.3815(4)  .16089(7)  -.0730(4)  .0465(5) Uani d . 1 . . C
  H5  -.3859  .1470  .0643  .057(6) Uiso calc R 1 . . H
  C1  -.2683(4)  .05304(6)  -.3474(4)  .0429(5) Uani d . 1 . . C
  C8  -.3733(5)  .20236(8)  -.4799(4)  .0610(6) Uani d . 1 . . C
  H8  -.3711  .2163  -.6177  .071(8) Uiso calc R 1 . . H
  C7  -.5452(5)  .21557(8)  -.3691(5)  .0621(6) Uani d . 1 . . C
  H7  -.6585  .2386  -.4316  .096(9) Uiso calc R 1 . . H
  C6  -.5500(4)  .19488(7)  -.1670(4)  .0564(6) Uani d . 1 . . C
  H6  -.6671  .2038  -.0930  .075(8) 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
  Cl  .0438(2)  .0725(4)  .0405(2)  -.0043(3)  .00592(19)  -.0035(3)
  O2  .0480(8)  .0600(10)  .0461(9)  -.0068(7)  .0224(7)  .0063(7)
  O1  .0775(11)  .0505(9)  .0483(8)  -.0010(7)  .0315(8)  -.0006(7)
  C4  .0415(10)  .0366(11)  .0351(9)  -.0055(8)  .0087(9)  -.0034(8)
  O3  .0460(9)  .0489(10)  .0672(10)  .0082(7)  .0131(8)  .0163(8)
  N1  .0483(11)  .0662(14)  .0605(13)  -.0020(9)  .0067(11)  -.0141(10)
  C3  .0355(10)  .0451(12)  .0367(10)  -.0031(8)  .0134(9)  .0004(8)
  C2  .0330(9)  .0437(12)  .0409(11)  .0019(8)  .0117(8)  .0064(8)
  C9  .0536(12)  .0475(13)  .0410(11)  -.0073(11)  .0171(10)  -.0031(9)
  C5  .0434(11)  .0500(12)  .0483(12)  .0009(10)  .0176(10)  .0010(10)
  C1  .0513(12)  .0324(11)  .0461(11)  .0011(8)  .0167(10)  .0004(8)
  C8  .0828(16)  .0474(13)  .0422(11)  -.0028(12)  .0037(12)  .0060(10)
  C7  .0594(13)  .0495(14)  .0636(14)  .0059(11)  -.0015(11)  -.0016(12)
  C6  .0492(12)  .0553(15)  .0630(15)  .0058(10)  .0147(12)  -.0044(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
  Cl C3 . 1.7987(19) yes
  O2 C2 . 1.390(2) yes
  O2 H21 .  .8200 ?
  O1 C1 . 1.235(2) yes
  C4 C5 . 1.386(3) yes
  C4 C9 . 1.388(3) yes
  C4 C3 . 1.503(3) yes
  O3 C2 . 1.404(2) yes
  O3 H31 .  .8200 ?
  N1 C1 . 1.308(3) yes
  N1 H1 .  .8600 ?
  N1 H2 .  .8600 ?
  C3 C2 . 1.539(3) yes
  C3 H3 .  .9800 ?
  C2 C1 . 1.544(3) yes
  C9 C8 . 1.381(3) yes
  C9 H9 .  .9300 ?
  C5 C6 . 1.378(3) yes
  C5 H5 .  .9300 ?
  C8 C7 . 1.375(3) yes
  C8 H8 .  .9300 ?
  C7 C6 . 1.369(4) yes
  C7 H7 .  .9300 .
  C6 H6 .  .9300 .
_cod_database_code 2011323