#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012119.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_2012119
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  996
_journal_page_last  998
_publ_section_title
;
Conformational polymorphs of the N-methylamide of
2-cyano-5-phenylpent-2-en-4-ynoic acid
;
loop_
_publ_author_name
  'Borbulevych, Oleg Ya.'
  'Golding, Igor R.'
  'Shchegolikhin, Alexander N.'
  'Klemenkova, Zinaida S.'
  'Antipin, Mikhail Yu.'
_chemical_formula_moiety  'C13 H10 N2 O'
_chemical_formula_sum  'C13 H10 N2 O'
_chemical_formula_weight  210.23
_chemical_melting_point  381
_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  11.9794(18)
_cell_length_b  8.9951(13)
_cell_length_c  10.0786(16)
_cell_angle_alpha  90
_cell_angle_beta  101.557(3)
_cell_angle_gamma  90
_cell_volume  1064.0(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  110(2)
_exptl_crystal_density_diffrn  1.312
_diffrn_ambient_temperature  110(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
  O1  .45358(7)  .25582(10)  .31185(8)  .0277(2) Uani d . 1 . . O
  N1  .69725(10)  .13868(14)  .72697(11)  .0377(3) Uani d . 1 . . N
  N2  .45292(8)  .29913(10)  .53215(9)  .0203(2) Uani d . 1 . . N
  H2  .4751(13)  .2680(17)  .6192(17)  .035(4) Uiso d . 1 . . H
  C1  .49430(9)  .23537(12)  .43267(11)  .0196(2) Uani d . 1 . . C
  C2  .59765(9)  .13833(11)  .47501(10)  .0196(2) Uani d . 1 . . C
  C3  .63525(9)  .05662(12)  .38099(12)  .0230(2) Uani d . 1 . . C
  H3  .5905(13)  .0602(18)  .2920(17)  .038(4) Uiso d . 1 . . H
  C4  .73229(9)  -.03567(12)  .40165(11)  .0232(2) Uani d . 1 . . C
  C5  .81166(9)  -.11817(12)  .40337(11)  .0222(2) Uani d . 1 . . C
  C6  .65475(10)  .13724(13)  .61427(12)  .0247(2) Uani d . 1 . . C
  C7  .89937(9)  -.22331(12)  .39560(11)  .0207(2) Uani d . 1 . . C
  C8 1.00752(10)  -.21557(13)  .47945(12)  .0239(2) Uani d . 1 . . C
  H8 1.0228(12)  -.1395(16)  .5478(15)  .026(3) Uiso d . 1 . . H
  C9 1.09029(10)  -.31896(14)  .46542(12)  .0274(3) Uani d . 1 . . C
  H9 1.1645(13)  -.3144(16)  .5249(15)  .030(4) Uiso d . 1 . . H
  C10 1.06531(10)  -.43096(14)  .36945(13)  .0286(3) Uani d . 1 . . C
  H10 1.1218(12)  -.5026(17)  .3544(15)  .028(4) Uiso d . 1 . . H
  C11  .95755(11)  -.44116(13)  .28754(12)  .0276(3) Uani d . 1 . . C
  H11  .9390(12)  -.5184(17)  .2246(16)  .033(4) Uiso d . 1 . . H
  C12  .87504(10)  -.33771(13)  .29904(11)  .0240(2) Uani d . 1 . . C
  H12  .7981(13)  -.3457(17)  .2460(15)  .031(4) Uiso d . 1 . . H
  C13  .35410(10)  .39571(14)  .50063(12)  .0242(2) Uani d . 1 . . C
  H13A  .2841(16)  .341(2)  .4605(19)  .052(5) Uiso d . 1 . . H
  H13B  .3414(13)  .4378(18)  .5882(17)  .041(4) Uiso d . 1 . . H
  H13C  .3675(13)  .4750(19)  .4387(17)  .041(4) Uiso d . 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
  O1  .0281(4)  .0365(5)  .0180(4)  .0089(4)  .0033(3)  .0015(3)
  N1  .0360(6)  .0466(7)  .0274(5)  .0149(5)  -.0009(4)  -.0019(5)
  N2  .0211(4)  .0212(4)  .0190(4)  .0020(3)  .0047(3)  .0013(3)
  C1  .0205(5)  .0191(5)  .0195(5)  .0003(4)  .0047(4)  .0014(4)
  C2  .0196(5)  .0180(5)  .0213(5)  -.0001(4)  .0041(4)  .0020(4)
  C3  .0227(5)  .0218(5)  .0247(5)  -.0001(4)  .0053(4)  .0003(4)
  C4  .0252(5)  .0202(5)  .0253(5)  -.0006(4)  .0075(4)  -.0023(4)
  C5  .0234(5)  .0192(5)  .0248(5)  -.0033(4)  .0070(4)  -.0010(4)
  C6  .0235(5)  .0251(5)  .0255(5)  .0064(4)  .0049(4)  .0009(4)
  C7  .0224(5)  .0180(5)  .0229(5)  -.0001(4)  .0078(4)  .0023(4)
  C8  .0249(5)  .0227(5)  .0241(5)  -.0027(4)  .0049(4)  .0013(4)
  C9  .0216(5)  .0308(6)  .0295(6)  .0015(4)  .0043(4)  .0071(5)
  C10  .0282(6)  .0281(6)  .0319(6)  .0080(5)  .0116(5)  .0050(5)
  C11  .0338(6)  .0251(6)  .0256(5)  .0017(5)  .0096(5)  -.0029(5)
  C12  .0239(5)  .0246(5)  .0237(5)  -.0002(4)  .0051(4)  -.0011(4)
  C13  .0236(5)  .0234(5)  .0269(5)  .0046(4)  .0080(4)  .0021(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
  O1 C1 . 1.2315(13) yes
  N1 C6 . 1.1480(16) yes
  N2 C1 . 1.3338(14) yes
  N2 C13 . 1.4513(14) yes
  C1 C2 . 1.5050(15) yes
  C2 C3 . 1.3462(15) yes
  C2 C6 . 1.4329(15) yes
  C3 C4 . 1.4096(15) yes
  C4 C5 . 1.2035(15) yes
  C5 C7 . 1.4274(15) yes
  C7 C8 . 1.3996(16) no
  C7 C12 . 1.4062(16) no
  C8 C9 . 1.3872(17) no
  C9 C10 . 1.3871(18) no
  C10 C11 . 1.3889(18) no
  C11 C12 . 1.3792(16) no
  N2 H2 .  .908(16) no
  C3 H3 .  .949(17) no
  C8 H8 .  .962(15) no
  C9 H9 .  .969(16) no
  C10 H10 .  .968(15) no
  C11 H11 .  .937(16) no
  C12 H12 .  .971(15) no
  C13 H13A .  .984(19) no
  C13 H13B .  .999(16) no
  C13 H13C .  .982(17) no