#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011320.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_2011320
_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           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
  'Lah, Nina'
  'Leban, Ivan'
  "Majcen-Le Mar\'echal, Alenka"
  'Le Grel, Philippe'
  'Robert, Albert'
  'Sieler, Joachim'
  'Giester, Gerald'
_chemical_formula_moiety  'C10 H7 Cl N2 O2'
_chemical_formula_sum  'C10 H7 Cl N2 O2'
_chemical_formula_weight  222.63
_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  4.9992(8)
_cell_length_b  12.694(3)
_cell_length_c  16.442(3)
_cell_angle_alpha  90.00
_cell_angle_beta  93.540(10)
_cell_angle_gamma  90.00
_cell_volume  1041.4(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.420
_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
  N1  .7265(3)  .03484(16)  -.41529(10)  .0612(5) Uani d . 1 . . N
  H1  .7222  .0306  -.4676  .068(7) Uiso calc R 1 . . H
  H2  .8713  .0541  -.3884  .083(8) Uiso calc R 1 . . H
  C1  .5113(3)  .01177(14)  -.37641(11)  .0460(4) Uani d . 1 . . C
  O1  .2951(2)  -.01638(12)  -.40846(8)  .0591(4) Uani d . 1 . . O
  C2  .5379(3)  .02381(14)  -.28500(10)  .0458(4) Uani d . 1 . . C
  C10  .3935(4)  -.05536(15)  -.24065(11)  .0534(4) Uani d . 1 . . C
  N2  .2806(5)  -.11797(15)  -.20777(13)  .0795(6) Uani d . 1 . . N
  C3  .5770(4)  .13093(15)  -.24897(12)  .0521(4) Uani d . 1 . . C
  H3  .5857  .1889  -.2882  .065(6) Uiso calc R 1 . . H
  O2  .7912(2)  .05587(13)  -.24926(8)  .0618(4) Uani d . 1 . . O
  C4  .4738(4)  .15929(14)  -.16894(11)  .0508(4) Uani d . 1 . . C
  C5  .2670(4)  .23174(16)  -.16634(13)  .0577(5) Uani d . 1 . . C
  H5  .1976  .2631  -.2142  .054(5) Uiso calc R 1 . . H
  C6  .1631(4)  .25776(17)  -.09257(15)  .0644(5) Uani d . 1 . . C
  H6  .0219  .3052  -.0907  .092(8) Uiso calc R 1 . . H
  C7  .2730(4)  .21197(17)  -.02199(13)  .0607(5) Uani d . 1 . . C
  C8  .4810(5)  .14142(18)  -.02315(12)  .0642(5) Uani d . 1 . . C
  H8  .5532  .1118  .0251  .081(7) Uiso calc R 1 . . H
  C9  .5820(4)  .11482(17)  -.09691(12)  .0601(5) Uani d . 1 . . C
  H9  .7226  .0670  -.0983  .075(7) Uiso calc R 1 . . H
  Cl  .13798(15)  .24047(7)  .07086(4)  .0936(3) Uani d . 1 . . Cl
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
  N1  .0338(7)  .0949(13)  .0556(9)  -.0122(7)  .0080(6)  -.0042(8)
  C1  .0327(7)  .0515(9)  .0544(9)  .0011(6)  .0065(6)  -.0012(7)
  O1  .0327(6)  .0863(10)  .0589(7)  -.0083(6)  .0072(5)  -.0086(7)
  C2  .0344(7)  .0494(9)  .0537(9)  .0004(6)  .0045(6)  .0023(7)
  C10  .0597(10)  .0432(9)  .0586(10)  .0059(8)  .0140(8)  .0004(8)
  N2  .1039(15)  .0507(10)  .0877(13)  -.0041(10)  .0376(11)  .0039(9)
  C3  .0487(9)  .0516(10)  .0560(10)  -.0070(7)  .0028(7)  .0024(8)
  O2  .0366(6)  .0857(10)  .0626(7)  .0000(6)  -.0006(5)  -.0085(7)
  C4  .0502(9)  .0456(9)  .0567(10)  -.0089(7)  .0044(7)  -.0022(7)
  C5  .0561(10)  .0504(10)  .0665(11)  -.0034(8)  .0026(8)  .0027(9)
  C6  .0577(11)  .0549(11)  .0815(14)  .0004(9)  .0117(9)  -.0070(10)
  C7  .0627(11)  .0571(11)  .0635(11)  -.0100(9)  .0119(9)  -.0127(9)
  C8  .0729(13)  .0637(12)  .0555(11)  -.0009(10)  .0009(9)  -.0017(9)
  C9  .0600(10)  .0581(11)  .0618(11)  .0051(9)  .0017(8)  -.0028(9)
  Cl  .0949(5)  .1114(6)  .0768(4)  .0013(4)  .0235(3)  -.0278(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
  N1 C1 . 1.318(2) yes
  N1 H1 .  .8600 ?
  N1 H2 .  .8600 ?
  C1 O1 . 1.226(2) yes
  C1 C2 . 1.508(2) yes
  C2 O2 . 1.422(2) yes
  C2 C10 . 1.459(2) yes
  C2 C3 . 1.491(3) yes
  C10 N2 . 1.132(3) yes
  C3 O2 . 1.434(2) yes
  C3 C4 . 1.487(3) yes
  C3 H3 .  .9800 ?
  C4 C5 . 1.386(3) yes
  C4 C9 . 1.391(3) yes
  C5 C6 . 1.389(3) yes
  C5 H5 .  .9300 ?
  C6 C7 . 1.381(3) yes
  C6 H6 .  .9300 ?
  C7 C8 . 1.373(3) yes
  C7 Cl . 1.745(2) yes
  C8 C9 . 1.384(3) yes
  C8 H8 .  .9300 ?
  C9 H9 .  .9300 ?
_cod_database_code 2011320