#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2009013.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_2009013
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  1692
_journal_page_last  1698
_publ_section_title
;
`Push-pull' effects in nitroethenamines
;
loop_
_publ_author_name
  'Linden, Anthony'
  'Moya Argilagos, Dally'
  'Heimgartner, Heinz'
  "Garc\'ia Trimi\~no, Mar\'ia I."
  "Mac\'ias Cabrera, Arturo"
_chemical_formula_moiety  'C16 H20 N4 O3 S '
_chemical_formula_sum  'C16 H20 N4 O3 S '
_chemical_formula_weight  348.42
_chemical_melting_point  '447.5-448'
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  ?
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  11.9391(8)
_cell_length_b  14.4523(13)
_cell_length_c  10.7398(9)
_cell_angle_alpha  90
_cell_angle_beta  108.930(5)
_cell_angle_gamma  90
_cell_volume  1752.9(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  173.0(10)
_exptl_crystal_density_diffrn  1.320
_diffrn_ambient_temperature  173.0(10)
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
  S  .91169(5)  .61074(5)  .07821(5)  .03102(15) Uani d . 1 . . S
  O1  .95094(14)  .59980(13)  .51437(14)  .0322(4) Uani d . 1 . . O
  O2 1.13434(13)  .64297(12)  .54911(14)  .0328(4) Uani d . 1 . . O
  O3  .67444(14)  .53242(14)  .07644(15)  .0422(5) Uani d . 1 . . O
  N1  .82205(14)  .56343(13)  .27155(17)  .0228(4) Uani d . 1 . . N
  H1  .840(2)  .560(2)  .355(3)  .043(8) Uiso d . 1 . . H
  N2 1.03352(15)  .62288(13)  .47047(16)  .0229(4) Uani d . 1 . . N
  N3 1.14537(14)  .75012(13)  .31705(16)  .0215(3) Uani d . 1 . . N
  N4 1.19165(14)  .60043(13)  .27263(16)  .0224(4) Uani d . 1 . . N
  C1  .91323(16)  .59872(14)  .23329(19)  .0199(4) Uani d . 1 . . C
  C2 1.01678(16)  .62646(13)  .33722(18)  .0188(4) Uani d . 1 . . C
  C3 1.12158(16)  .66079(14)  .30580(18)  .0188(4) Uani d . 1 . . C
  C4  .71102(17)  .53102(15)  .1957(2)  .0228(4) Uani d . 1 . . C
  C5  .64440(17)  .49040(15)  .2772(2)  .0233(4) Uani d . 1 . . C
  H5  .6759  .4934  .3704  .028 Uiso calc R 1 . . H
  C6  .54028(17)  .44961(15)  .2195(2)  .0229(4) Uani d . 1 . . C
  H6  .5081  .4565  .1267  .028 Uiso calc R 1 . . H
  C7  .46934(17)  .39539(14)  .2822(2)  .0219(4) Uani d . 1 . . C
  C8  .37090(18)  .34795(15)  .2005(2)  .0256(4) Uani d . 1 . . C
  H8  .3502  .3540  .1076  .031 Uiso calc R 1 . . H
  C9  .30287(19)  .29208(16)  .2531(2)  .0308(5) Uani d . 1 . . C
  H9  .2371  .2593  .1963  .037 Uiso calc R 1 . . H
  C10  .3307(2)  .28411(18)  .3877(3)  .0361(6) Uani d . 1 . . C
  H10  .2839  .2462  .4237  .043 Uiso calc R 1 . . H
  C11  .4276(2)  .3316(2)  .4707(2)  .0387(6) Uani d . 1 . . C
  H11  .4463  .3265  .5634  .046 Uiso calc R 1 . . H
  C12  .49703(19)  .38652(17)  .4189(2)  .0304(5) Uani d . 1 . . C
  H12  .5636  .4182  .4763  .037 Uiso calc R 1 . . H
  C13 1.05432(19)  .81778(16)  .3213(2)  .0284(5) Uani d . 1 . . C
  H131  .9766  .7968  .2640  .043 Uiso calc R 1 . . H
  H132 1.0726  .8781  .2908  .043 Uiso calc R 1 . . H
  H133 1.0532  .8234  .4118  .043 Uiso calc R 1 . . H
  C14 1.26580(18)  .78734(16)  .3470(2)  .0294(5) Uani d . 1 . . C
  H141 1.3236  .7385  .3857  .044 Uiso calc R 1 . . H
  H142 1.2770  .8387  .4095  .044 Uiso calc R 1 . . H
  H143 1.2771  .8096  .2657  .044 Uiso calc R 1 . . H
  C15 1.2572(2)  .62330(18)  .1824(2)  .0316(5) Uani d . 1 . . C
  H151 1.2331  .6846  .1441  .047 Uiso calc R 1 . . H
  H152 1.2400  .5771  .1119  .047 Uiso calc R 1 . . H
  H153 1.3423  .6235  .2308  .047 Uiso calc R 1 . . H
  C16 1.1807(2)  .50097(16)  .2917(2)  .0304(5) Uani d . 1 . . C
  H161 1.1393  .4909  .3559  .046 Uiso calc R 1 . . H
  H162 1.2597  .4732  .3244  .046 Uiso calc R 1 . . H
  H163 1.1356  .4723  .2077  .046 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
  S  .0222(2)  .0528(4)  .0181(2)  -.0039(3)  .00649(19)  .0023(2)
  O1  .0310(8)  .0470(10)  .0234(7)  -.0149(7)  .0157(6)  -.0052(7)
  O2  .0261(8)  .0477(10)  .0195(7)  -.0107(7)  .0004(6)  .0009(7)
  O3  .0285(8)  .0674(13)  .0252(8)  -.0202(9)  .0011(7)  .0061(8)
  N1  .0185(8)  .0309(10)  .0197(8)  -.0034(7)  .0072(7)  .0014(7)
  N2  .0211(8)  .0284(10)  .0194(8)  -.0042(7)  .0067(7)  .0000(7)
  N3  .0199(8)  .0221(8)  .0235(8)  -.0018(7)  .0083(7)  .0020(7)
  N4  .0188(8)  .0270(9)  .0231(8)  .0008(7)  .0092(6)  .0027(7)
  C1  .0167(8)  .0221(10)  .0212(9)  .0002(8)  .0063(7)  .0012(8)
  C2  .0171(8)  .0215(10)  .0188(8)  -.0018(7)  .0072(7)  .0003(8)
  C3  .0153(8)  .0240(10)  .0159(8)  -.0013(7)  .0034(7)  .0035(8)
  C4  .0175(9)  .0253(11)  .0244(9)  -.0012(8)  .0054(8)  .0015(8)
  C5  .0199(9)  .0277(11)  .0238(9)  .0006(8)  .0089(8)  .0026(8)
  C6  .0207(9)  .0248(11)  .0230(9)  -.0004(8)  .0067(8)  .0022(8)
  C7  .0178(8)  .0210(10)  .0270(10)  .0012(8)  .0071(7)  .0028(8)
  C8  .0241(10)  .0252(11)  .0276(10)  -.0012(9)  .0085(8)  -.0018(9)
  C9  .0247(10)  .0241(11)  .0407(13)  -.0069(9)  .0068(9)  .0002(10)
  C10  .0270(11)  .0366(14)  .0442(14)  -.0057(10)  .0107(10)  .0162(11)
  C11  .0307(12)  .0530(17)  .0300(11)  -.0044(11)  .0064(10)  .0156(12)
  C12  .0219(10)  .0378(13)  .0283(11)  -.0045(9)  .0035(8)  .0060(10)
  C13  .0320(11)  .0255(11)  .0296(11)  .0034(9)  .0126(9)  .0031(9)
  C14  .0236(10)  .0305(12)  .0334(12)  -.0078(9)  .0082(9)  .0014(10)
  C15  .0283(11)  .0408(14)  .0327(11)  .0010(10)  .0196(9)  .0023(10)
  C16  .0284(11)  .0263(11)  .0392(12)  .0038(9)  .0147(10)  .0021(10)
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
  S C1 . 1.669(2) yes
  O1 N2 . 1.268(2) ?
  O2 N2 . 1.260(2) ?
  O3 C4 . 1.211(2) ?
  N1 C1 . 1.380(2) yes
  N1 C4 . 1.393(3) yes
  N1 H1 .  .85(3) ?
  N2 C2 . 1.380(2) yes
  N3 C3 . 1.319(3) yes
  N3 C14 . 1.470(3) ?
  N3 C13 . 1.474(3) ?
  N4 C3 . 1.335(3) yes
  N4 C16 . 1.464(3) ?
  N4 C15 . 1.468(2) ?
  C1 C2 . 1.428(3) yes
  C2 C3 . 1.483(2) yes
  C4 C5 . 1.482(3) yes
  C5 C6 . 1.333(3) yes
  C5 H5 .  .9500 ?
  C6 C7 . 1.467(3) ?
  C6 H6 .  .9500 ?
  C7 C8 . 1.397(3) ?
  C7 C12 . 1.403(3) ?
  C8 C9 . 1.389(3) ?
  C8 H8 .  .9500 ?
  C9 C10 . 1.379(3) ?
  C9 H9 .  .9500 ?
  C10 C11 . 1.391(3) ?
  C10 H10 .  .9500 ?
  C11 C12 . 1.388(3) ?
  C11 H11 .  .9500 ?
  C12 H12 .  .9500 ?
  C13 H131 .  .9800 ?
  C13 H132 .  .9800 ?
  C13 H133 .  .9800 ?
  C14 H141 .  .9800 ?
  C14 H142 .  .9800 ?
  C14 H143 .  .9800 ?
  C15 H151 .  .9800 ?
  C15 H152 .  .9800 ?
  C15 H153 .  .9800 ?
  C16 H161 .  .9800 ?
  C16 H162 .  .9800 ?
  C16 H163 .  .9800 ?