#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014558.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_2014558
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o781
_journal_page_last  o785
_publ_section_title
;
Polymorphism and solvolysis of
2-cyano-3-[4-(N,N-diethylamino)phenyl]prop-2-enethioamide
;
loop_
_publ_author_name
  'Nesterov, Vladimir N.'
  'Nesterov, Volodymyr V.'
_chemical_formula_moiety  'C14 H17 N3 S, 0.25C2 H3 N'
_chemical_formula_sum  'C14.5 H17.75 3.25 S1'
_chemical_formula_weight  269.64
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
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'
  '-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  39.370(8)
_cell_length_b  8.8800(18)
_cell_length_c  17.056(3)
_cell_angle_alpha  90.00
_cell_angle_beta  101.19(3)
_cell_angle_gamma  90.00
_cell_volume  5850(2)
_cell_formula_units_Z  16
_cell_measurement_temperature  298(2)
_exptl_crystal_density_diffrn  1.225
_diffrn_ambient_temperature  298(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
  S1A 0.30718(2) 0.24174(11) 0.27209(5) 0.0478(3) Uani d . 1 . . S
  N1A 0.32656(7) 0.2712(4) -0.01178(18) 0.0536(8) Uani d . 1 . . N
  N2A 0.35114(7) 0.3122(3) 0.18127(16) 0.0512(8) Uani d . 1 . . N
  H2AA 0.3580 0.3148 0.1363 0.061 Uiso calc R 1 . . H
  H2AB 0.3637 0.3513 0.2232 0.061 Uiso calc R 1 . . H
  N3A 0.18347(7) -0.2138(3) -0.13861(16) 0.0453(7) Uani d . 1 . . N
  C1A 0.25282(7) 0.0149(3) 0.04174(17) 0.0338(7) Uani d . 1 . . C
  C2A 0.22709(8) -0.0820(4) 0.05954(19) 0.0419(8) Uani d . 1 . . C
  H2AC 0.2253 -0.0953 0.1127 0.050 Uiso calc R 1 . . H
  C3A 0.20450(8) -0.1576(4) 0.00131(19) 0.0419(8) Uani d . 1 . . C
  H3AA 0.1878 -0.2201 0.0159 0.050 Uiso calc R 1 . . H
  C4A 0.20615(8) -0.1424(3) -0.0792(2) 0.0394(8) Uani d . 1 . . C
  C5A 0.23241(8) -0.0470(4) -0.09762(18) 0.0425(8) Uani d . 1 . . C
  H5AA 0.2345 -0.0352 -0.1507 0.051 Uiso calc R 1 . . H
  C6A 0.25474(8) 0.0280(4) -0.03933(18) 0.0398(8) Uani d . 1 . . C
  H6AA 0.2717 0.0893 -0.0537 0.048 Uiso calc R 1 . . H
  C7A 0.27457(8) 0.0913(3) 0.10672(17) 0.0351(7) Uani d . 1 . . C
  H7AA 0.2687 0.0735 0.1562 0.042 Uiso calc R 1 . . H
  C8A 0.30202(7) 0.1846(3) 0.10968(17) 0.0318(7) Uani d . 1 . . C
  C9A 0.31473(7) 0.2292(4) 0.04067(19) 0.0366(8) Uani d . 1 . . C
  C10A 0.32134(8) 0.2480(3) 0.18593(17) 0.0351(7) Uani d . 1 . . C
  C11A 0.15694(9) -0.3130(4) -0.1196(2) 0.0538(10) Uani d . 1 . . C
  H11B 0.1664 -0.3695 -0.0717 0.065 Uiso calc R 1 . . H
  H11C 0.1503 -0.3844 -0.1629 0.065 Uiso calc R 1 . . H
  C12A 0.12486(9) -0.2282(5) -0.1065(3) 0.0697(12) Uani d . 1 . . C
  H12A 0.1078 -0.2988 -0.0959 0.105 Uiso calc R 1 . . H
  H12B 0.1155 -0.1710 -0.1535 0.105 Uiso calc R 1 . . H
  H12C 0.1310 -0.1613 -0.0617 0.105 Uiso calc R 1 . . H
  C13A 0.18095(9) -0.1790(4) -0.2231(2) 0.0517(9) Uani d . 1 . . C
  H13A 0.1881 -0.0756 -0.2281 0.062 Uiso calc R 1 . . H
  H13B 0.1569 -0.1871 -0.2498 0.062 Uiso calc R 1 . . H
  C14A 0.20243(10) -0.2797(5) -0.2647(2) 0.0678(12) Uani d . 1 . . C
  H14B 0.1995 -0.2507 -0.3198 0.102 Uiso calc R 1 . . H
  H14C 0.1951 -0.3822 -0.2613 0.102 Uiso calc R 1 . . H
  H14D 0.2264 -0.2705 -0.2396 0.102 Uiso calc R 1 . . H
  S1B 0.41456(2) 0.47668(11) 0.30624(5) 0.0500(3) Uani d . 1 . . S
  N1B 0.40596(8) 0.6653(4) 0.58260(19) 0.0717(11) Uani d . 1 . . N
  N2B 0.37145(7) 0.5157(3) 0.40298(16) 0.0463(7) Uani d . 1 . . N
  H2BA 0.3660 0.5484 0.4464 0.056 Uiso calc R 1 . . H
  H2BB 0.3564 0.4690 0.3683 0.056 Uiso calc R 1 . . H
  N3B 0.57131(7) 0.9542(3) 0.63859(16) 0.0446(7) Uani d . 1 . . N
  C1B 0.48736(8) 0.7335(3) 0.49443(18) 0.0364(7) Uani d . 1 . . C
  C2B 0.52112(8) 0.7223(4) 0.4801(2) 0.0445(8) Uani d . 1 . . C
  H2BC 0.5250 0.6643 0.4372 0.053 Uiso calc R 1 . . H
  C3B 0.54872(8) 0.7935(4) 0.5268(2) 0.0456(9) Uani d . 1 . . C
  H3BA 0.5708 0.7806 0.5159 0.055 Uiso calc R 1 . . H
  C4B 0.54420(8) 0.8859(4) 0.59123(18) 0.0383(8) Uani d . 1 . . C
  C5B 0.50987(8) 0.9042(4) 0.60238(18) 0.0407(8) Uani d . 1 . . C
  H5BA 0.5055 0.9691 0.6421 0.049 Uiso calc R 1 . . H
  C6B 0.48296(8) 0.8299(4) 0.55692(18) 0.0400(8) Uani d . 1 . . C
  H6BA 0.4609 0.8432 0.5675 0.048 Uiso calc R 1 . . H
  C7B 0.46041(8) 0.6522(3) 0.44399(18) 0.0368(8) Uani d . 1 . . C
  H7BA 0.4663 0.6158 0.3973 0.044 Uiso calc R 1 . . H
  C8B 0.42750(8) 0.6185(3) 0.45210(18) 0.0348(7) Uani d . 1 . . C
  C9B 0.41600(8) 0.6480(4) 0.5246(2) 0.0427(8) Uani d . 1 . . C
  C10B 0.40321(8) 0.5375(3) 0.38965(18) 0.0357(7) Uani d . 1 . . C
  C11B 0.60725(8) 0.9184(4) 0.6357(2) 0.0531(10) Uani d . 1 . . C
  H11A 0.6084 0.8152 0.6179 0.064 Uiso calc R 1 . . H
  H11D 0.6210 0.9252 0.6893 0.064 Uiso calc R 1 . . H
  C12B 0.62301(10) 1.0190(5) 0.5817(3) 0.0750(13) Uani d . 1 . . C
  H12D 0.6464 0.9877 0.5821 0.113 Uiso calc R 1 . . H
  H12E 0.6230 1.1211 0.6002 0.113 Uiso calc R 1 . . H
  H12F 0.6098 1.0126 0.5283 0.113 Uiso calc R 1 . . H
  C13B 0.56671(9) 1.0554(4) 0.7037(2) 0.0514(9) Uani d . 1 . . C
  H13C 0.5458 1.1141 0.6868 0.062 Uiso calc R 1 . . H
  H13D 0.5861 1.1249 0.7146 0.062 Uiso calc R 1 . . H
  C14B 0.56427(11) 0.9718(5) 0.7793(2) 0.0748(13) Uani d . 1 . . C
  H14A 0.5613 1.0425 0.8200 0.112 Uiso calc R 1 . . H
  H14E 0.5851 0.9151 0.7969 0.112 Uiso calc R 1 . . H
  H14F 0.5448 0.9045 0.7692 0.112 Uiso calc R 1 . . H
  N1S 0.5000 0.7142(8) 0.2500 0.110(2) Uani d S 1 . . N
  C1S 0.5000 0.5886(9) 0.2500 0.0738(18) Uani d S 1 . . C
  C2S 0.5000 0.4252(8) 0.2500 0.130(3) Uani d S 1 . . C
  H2SA 0.5178 0.3891 0.2925 0.195 Uiso calc PR 0.50 . . H
  H2SB 0.5043 0.3891 0.1998 0.195 Uiso calc PR 0.50 . . H
  H2SC 0.4779 0.3891 0.2577 0.195 Uiso calc PR 0.50 . . 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
  S1A 0.0487(5) 0.0586(6) 0.0382(5) -0.0023(5) 0.0134(4) -0.0077(4)
  N1A 0.0501(18) 0.062(2) 0.0504(18) -0.0092(16) 0.0147(15) -0.0046(16)
  N2A 0.0421(16) 0.072(2) 0.0395(16) -0.0167(16) 0.0074(13) -0.0171(15)
  N3A 0.0458(16) 0.0388(17) 0.0479(17) -0.0098(14) 0.0009(13) -0.0044(14)
  C1A 0.0325(17) 0.0321(18) 0.0349(18) 0.0000(15) 0.0016(13) 0.0021(15)
  C2A 0.045(2) 0.042(2) 0.0380(18) -0.0014(17) 0.0060(15) 0.0076(16)
  C3A 0.0388(19) 0.036(2) 0.049(2) -0.0070(16) 0.0047(16) 0.0044(16)
  C4A 0.0378(18) 0.0293(18) 0.048(2) 0.0005(15) -0.0003(15) -0.0012(15)
  C5A 0.046(2) 0.042(2) 0.0362(18) -0.0026(17) 0.0015(15) 0.0008(16)
  C6A 0.0393(18) 0.0347(19) 0.044(2) -0.0043(16) 0.0044(15) 0.0012(16)
  C7A 0.0363(18) 0.0352(19) 0.0335(17) 0.0080(15) 0.0058(14) 0.0022(15)
  C8A 0.0311(16) 0.0285(17) 0.0357(17) 0.0049(14) 0.0065(13) -0.0031(14)
  C9A 0.0307(17) 0.0345(19) 0.0425(19) 0.0004(15) 0.0020(15) -0.0100(16)
  C10A 0.0354(17) 0.0305(17) 0.0390(18) 0.0044(15) 0.0063(13) -0.0034(15)
  C11A 0.053(2) 0.045(2) 0.059(2) -0.0105(19) 0.0020(18) -0.0079(19)
  C12A 0.053(2) 0.077(3) 0.078(3) -0.005(2) 0.008(2) -0.012(2)
  C13A 0.052(2) 0.045(2) 0.052(2) -0.0050(18) -0.0037(18) -0.0031(18)
  C14A 0.083(3) 0.064(3) 0.054(2) 0.003(2) 0.007(2) -0.004(2)
  S1B 0.0437(5) 0.0612(6) 0.0456(5) -0.0129(5) 0.0098(4) -0.0153(5)
  N1B 0.056(2) 0.107(3) 0.056(2) -0.028(2) 0.0208(17) -0.022(2)
  N2B 0.0386(16) 0.0543(19) 0.0455(16) -0.0096(14) 0.0072(12) -0.0101(14)
  N3B 0.0406(16) 0.0371(16) 0.0520(17) -0.0047(14) -0.0012(13) -0.0032(14)
  C1B 0.0372(17) 0.0312(18) 0.0400(18) -0.0016(15) 0.0054(14) -0.0017(15)
  C2B 0.0408(19) 0.044(2) 0.049(2) -0.0027(17) 0.0105(16) -0.0077(17)
  C3B 0.0345(18) 0.042(2) 0.061(2) -0.0035(16) 0.0118(17) -0.0035(18)
  C4B 0.0382(18) 0.0311(18) 0.0439(19) -0.0045(15) 0.0033(15) 0.0037(16)
  C5B 0.0395(19) 0.039(2) 0.0432(19) -0.0051(16) 0.0071(15) -0.0074(16)
  C6B 0.0353(17) 0.040(2) 0.0444(19) -0.0032(16) 0.0072(15) -0.0022(16)
  C7B 0.0439(19) 0.0305(19) 0.0347(17) 0.0037(15) 0.0045(15) -0.0001(14)
  C8B 0.0345(17) 0.0324(18) 0.0378(18) -0.0013(15) 0.0074(14) -0.0017(15)
  C9B 0.0344(18) 0.048(2) 0.044(2) -0.0106(16) 0.0021(16) -0.0048(17)
  C10B 0.0342(17) 0.0295(18) 0.0422(18) 0.0005(14) 0.0042(14) 0.0086(15)
  C11B 0.041(2) 0.038(2) 0.075(3) -0.0047(17) -0.0037(18) 0.0073(19)
  C12B 0.058(3) 0.061(3) 0.111(4) -0.010(2) 0.029(2) 0.012(3)
  C13B 0.051(2) 0.042(2) 0.057(2) -0.0123(18) 0.0014(17) -0.0069(19)
  C14B 0.087(3) 0.078(3) 0.057(2) -0.015(3) 0.006(2) 0.003(2)
  N1S 0.142(6) 0.074(4) 0.134(6) 0.000 0.079(5) 0.000
  C1S 0.073(4) 0.081(5) 0.080(4) 0.000 0.045(3) 0.000
  C2S 0.149(8) 0.060(5) 0.212(10) 0.000 0.107(7) 0.000
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  S1A C10A . . 1.671(3) yes
  N1A C9A . . 1.148(4) yes
  N2A C10A . . 1.320(4) yes
  N2A H2AA . . 0.8600 no
  N2A H2AB . . 0.8600 no
  N3A C4A . . 1.369(4) yes
  N3A C11A . . 1.451(4) no
  N3A C13A . . 1.458(4) no
  C1A C6A . . 1.404(4) no
  C1A C2A . . 1.406(4) no
  C1A C7A . . 1.433(4) no
  C2A C3A . . 1.373(4) no
  C2A H2AC . . 0.9300 no
  C3A C4A . . 1.394(4) no
  C3A H3AA . . 0.9300 no
  C4A C5A . . 1.418(4) no
  C5A C6A . . 1.366(4) no
  C5A H5AA . . 0.9300 no
  C6A H6AA . . 0.9300 no
  C7A C8A . . 1.355(4) yes
  C7A H7AA . . 0.9300 no
  C8A C9A . . 1.422(4) yes
  C8A C10A . . 1.484(4) yes
  C11A C12A . . 1.524(5) no
  C11A H11B . . 0.9700 no
  C11A H11C . . 0.9700 no
  C12A H12A . . 0.9600 no
  C12A H12B . . 0.9600 no
  C12A H12C . . 0.9600 no
  C13A C14A . . 1.500(5) no
  C13A H13A . . 0.9700 no
  C13A H13B . . 0.9700 no
  C14A H14B . . 0.9600 no
  C14A H14C . . 0.9600 no
  C14A H14D . . 0.9600 no
  S1B C10B . . 1.662(3) yes
  N1B C9B . . 1.144(4) yes
  N2B C10B . . 1.328(4) yes
  N2B H2BA . . 0.8600 no
  N2B H2BB . . 0.8600 no
  N3B C4B . . 1.351(4) yes
  N3B C11B . . 1.460(4) no
  N3B C13B . . 1.467(4) no
  C1B C2B . . 1.401(4) no
  C1B C6B . . 1.404(4) no
  C1B C7B . . 1.426(4) no
  C2B C3B . . 1.371(4) no
  C2B H2BC . . 0.9300 no
  C3B C4B . . 1.410(4) no
  C3B H3BA . . 0.9300 no
  C4B C5B . . 1.410(4) no
  C5B C6B . . 1.356(4) no
  C5B H5BA . . 0.9300 no
  C6B H6BA . . 0.9300 no
  C7B C8B . . 1.363(4) yes
  C7B H7BA . . 0.9300 no
  C8B C9B . . 1.422(4) yes
  C8B C10B . . 1.473(4) yes
  C11B C12B . . 1.500(5) no
  C11B H11A . . 0.9700 no
  C11B H11D . . 0.9700 no
  C12B H12D . . 0.9600 no
  C12B H12E . . 0.9600 no
  C12B H12F . . 0.9600 no
  C13B C14B . . 1.508(5) no
  C13B H13C . . 0.9700 no
  C13B H13D . . 0.9700 no
  C14B H14A . . 0.9600 no
  C14B H14E . . 0.9600 no
  C14B H14F . . 0.9600 no
  N1S C1S . . 1.116(8) no
  C1S C2S . . 1.451(10) no
  C2S H2SA . . 0.9600 no
  C2S H2SB . . 0.9600 no
  C2S H2SC . . 0.9600 no