#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011321.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_2011321
_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 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/a'
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  'C11 H11 Br N2 O2'
_chemical_formula_sum  'C11 H11 Br N2 O2'
_chemical_formula_weight  283.13
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z'
_cell_length_a  5.934(3)
_cell_length_b  33.653(6)
_cell_length_c  6.1770(10)
_cell_angle_alpha  90.00
_cell_angle_beta  107.12(3)
_cell_angle_gamma  90.00
_cell_volume  1178.9(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.595
_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  .3428(5)  .20386(11)  -.0062(5)  .0629(9) Uani d . 1 . . N
  H2A  .2006  .2102  -.0799  .076 Uiso calc R 1 . . H
  H2B  .4532  .2058  -.0699  .076 Uiso calc R 1 . . H
  C1  .3912(5)  .19116(10)  .2027(6)  .0423(7) Uani d . 1 . . C
  O1  .2511(4)  .18707(9)  .3114(5)  .0628(7) Uani d . 1 . . O
  C2  .6521(5)  .17985(9)  .3159(5)  .0335(6) Uani d . 1 . . C
  O2  .7794(4)  .18555(8)  .1622(4)  .0458(6) Uani d . 1 . . O
  H1  .9209  .1853  .2295  .069 Uiso calc R 1 . . H
  C10  .7393(5)  .20611(11)  .5167(5)  .0430(7) Uani d . 1 . . C
  N2  .8137(6)  .22568(11)  .6711(5)  .0665(9) Uani d . 1 . . N
  C3  .6489(5)  .13651(10)  .3992(5)  .0344(6) Uani d . 1 . . C
  H4  .5452  .1359  .4968  .041 Uiso calc R 1 . . H
  Br  .96866(5)  .122066(11)  .58896(5)  .04902(14) Uani d . 1 . . Br
  C4  .5573(5)  .10630(10)  .2155(5)  .0365(6) Uani d . 1 . . C
  C5  .6653(6)  .09796(11)  .0501(5)  .0476(8) Uani d . 1 . . C
  H11  .8029  .1112  .0504  .057 Uiso calc R 1 . . H
  C6  .5689(6)  .06988(11)  -.1165(5)  .0501(8) Uani d . 1 . . C
  H15  .6417  .0650  -.2281  .060 Uiso calc R 1 . . H
  C7  .3659(6)  .04903(11)  -.1195(6)  .0490(8) Uani d . 1 . . C
  C8  .2618(6)  .05736(11)  .0473(6)  .0528(9) Uani d . 1 . . C
  H12  .1258  .0438  .0488  .063 Uiso calc R 1 . . H
  C9  .3546(6)  .08542(11)  .2123(6)  .0466(8) Uani d . 1 . . C
  H10  .2804  .0904  .3228  .056 Uiso calc R 1 . . H
  C11  .2620(8)  .01864(13)  -.2993(6)  .0695(12) Uani d . 1 . . C
  H17A  .3568  .0169  -.4009  .104 Uiso calc R 1 . . H
  H17B  .1045  .0264  -.3823  .104 Uiso calc R 1 . . H
  H17C  .2582  -.0068  -.2296  .104 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
  N1  .0498(15)  .066(2)  .0641(18)  .0076(15)  .0025(14)  .0218(17)
  C1  .0355(14)  .0292(19)  .0597(18)  .0006(12)  .0101(13)  .0060(15)
  O1  .0347(10)  .071(2)  .0892(18)  .0031(11)  .0282(12)  .0118(15)
  C2  .0303(12)  .0346(18)  .0370(13)  -.0006(11)  .0119(10)  .0040(12)
  O2  .0402(10)  .0551(16)  .0482(11)  -.0055(11)  .0225(9)  .0114(11)
  C10  .0392(14)  .039(2)  .0520(18)  .0018(14)  .0150(13)  .0036(16)
  N2  .0647(18)  .062(3)  .0671(18)  -.0017(17)  .0112(16)  -.0132(18)
  C3  .0355(13)  .0327(17)  .0388(14)  .0069(12)  .0168(11)  .0085(13)
  Br  .04734(18)  .0540(3)  .04557(18)  .01574(15)  .01338(13)  .01061(16)
  C4  .0400(14)  .0302(17)  .0434(15)  .0054(12)  .0184(12)  .0070(13)
  C5  .0512(16)  .045(2)  .0555(18)  -.0054(16)  .0291(15)  -.0004(17)
  C6  .066(2)  .041(2)  .0496(18)  .0000(17)  .0272(16)  -.0012(16)
  C7  .0592(18)  .032(2)  .0503(17)  .0059(15)  .0080(15)  .0051(15)
  C8  .0468(17)  .041(2)  .071(2)  -.0048(15)  .0183(16)  .0024(18)
  C9  .0448(15)  .042(2)  .0577(19)  .0010(14)  .0229(14)  .0027(16)
  C11  .090(3)  .050(3)  .060(2)  -.005(2)  .007(2)  -.0055(19)
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 . 1.308(4) yes
  N1 H2A .  .8600 ?
  N1 H2B .  .8600 ?
  C1 O1 . 1.221(4) yes
  C1 C2 . 1.547(4) yes
  C2 O2 . 1.390(3) yes
  C2 C10 . 1.486(4) yes
  C2 C3 . 1.548(4) yes
  O2 H1 .  .8200 ?
  C10 N2 . 1.136(4) yes
  C3 C4 . 1.501(4) yes
  C3 Br . 1.975(3) yes
  C3 H4 .  .9800 ?
  C4 C5 . 1.386(4) yes
  C4 C9 . 1.388(4) yes
  C5 C6 . 1.390(5) yes
  C5 H11 .  .9300 ?
  C6 C7 . 1.390(5) yes
  C6 H15 .  .9300 ?
  C7 C8 . 1.377(5) yes
  C7 C11 . 1.502(5) yes
  C8 C9 . 1.380(5) yes
  C8 H12 .  .9300 ?
  C9 H10 .  .9300 ?
  C11 H17A .  .9600 ?
  C11 H17B .  .9600 ?
  C11 H17C .  .9600 ?