data_2009012
_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  'C12 H14 N4 O3 S '
_chemical_formula_sum  'C12 H14 N4 O3 S '
_chemical_formula_weight  294.34
_chemical_melting_point  '449.3-449.4'
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  11.7761(16)
_cell_length_b  17.172(2)
_cell_length_c  6.825(4)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  1380.2(8)
_cell_formula_units_Z  4
_cell_measurement_temperature  173.0(10)
_exptl_crystal_density_diffrn  1.416
_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  .54356(5)  .21876(3)  .19490(9)  .03266(13) Uani d . 1 . . S
  O1  .59293(12)  -.03636(8)  .0343(2)  .0320(3) Uani d . 1 . . O
  O2  .77048(12)  -.00637(8)  -.0209(2)  .0320(3) Uani d . 1 . . O
  O3  .30306(13)  .16042(9)  .1417(3)  .0406(4) Uani d . 1 . . O
  N1  .45379(15)  .07639(9)  .1172(3)  .0264(3) Uani d . 1 . . N
  H1  .474(2)  .0288(14)  .084(3)  .030(6) Uiso d . 1 . . H
  N2  .67205(14)  .01448(9)  .0293(3)  .0260(3) Uani d . 1 . . N
  N3  .81849(14)  .14222(10)  .2328(3)  .0284(4) Uani d . 1 . . N
  H3  .804(2)  .1119(15)  .331(4)  .038(7) Uiso d . 1 . . H
  N4  .78145(15)  .18106(10)  -.0837(3)  .0274(4) Uani d . 1 . . N
  H4  .827(2)  .2188(14)  -.076(4)  .035(6) Uiso d . 1 . . H
  C1  .54568(17)  .12483(10)  .1272(3)  .0246(4) Uani d . 1 . . C
  C2  .65305(16)  .09083(11)  .0762(3)  .0240(4) Uani d . 1 . . C
  C3  .75643(16)  .14088(11)  .0736(3)  .0248(4) Uani d . 1 . . C
  C4  .33855(17)  .09430(12)  .1304(3)  .0270(4) Uani d . 1 . . C
  C5  .26146(16)  .02557(11)  .1261(3)  .0251(4) Uani d . 1 . . C
  C6  .29679(17)  -.05146(12)  .1344(3)  .0289(4) Uani d . 1 . . C
  H6  .3754  -.0632  .1455  .035 Uiso calc R 1 . . H
  C7  .21786(19)  -.11140(13)  .1268(4)  .0354(5) Uani d . 1 . . C
  H7  .2425  -.1640  .1332  .042 Uiso calc R 1 . . H
  C8  .1027(2)  -.09449(14)  .1096(4)  .0374(5) Uani d . 1 . . C
  H8  .0488  -.1356  .1026  .045 Uiso calc R 1 . . H
  C9  .06686(18)  -.01809(15)  .1026(3)  .0376(5) Uani d . 1 . . C
  H9  -.0118  -.0066  .0924  .045 Uiso calc R 1 . . H
  C10  .14531(17)  .04178(13)  .1104(3)  .0336(5) Uani d . 1 . . C
  H10  .1202  .0943  .1051  .040 Uiso calc R 1 . . H
  C11  .92073(18)  .18866(13)  .2549(4)  .0382(5) Uani d . 1 . . C
  H111  .9765  .1729  .1560  .057 Uiso calc R 1 . . H
  H112  .9525  .1805  .3860  .057 Uiso calc R 1 . . H
  H113  .9021  .2439  .2376  .057 Uiso calc R 1 . . H
  C12  .7111(2)  .18247(13)  -.2605(3)  .0347(5) Uani d . 1 . . C
  H121  .7008  .1292  -.3091  .052 Uiso calc R 1 . . H
  H122  .7485  .2140  -.3613  .052 Uiso calc R 1 . . H
  H123  .6369  .2051  -.2295  .052 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  .0318(2)  .0199(2)  .0463(3)  .0010(2)  .0037(2)  -.0055(2)
  O1  .0286(7)  .0218(7)  .0457(9)  -.0032(5)  .0039(7)  -.0047(6)
  O2  .0269(7)  .0254(7)  .0439(9)  .0041(6)  .0057(7)  -.0034(6)
  O3  .0331(8)  .0250(7)  .0637(12)  .0060(6)  .0011(8)  -.0001(7)
  N1  .0244(8)  .0216(7)  .0332(8)  .0007(7)  .0050(8)  -.0021(7)
  N2  .0285(8)  .0194(8)  .0302(8)  -.0011(6)  .0006(7)  -.0003(7)
  N3  .0270(8)  .0260(8)  .0322(9)  -.0015(6)  -.0027(7)  .0041(7)
  N4  .0291(8)  .0235(8)  .0296(9)  -.0042(7)  .0017(7)  .0016(7)
  C1  .0264(8)  .0222(8)  .0252(9)  .0002(8)  .0025(8)  .0007(7)
  C2  .0247(9)  .0196(8)  .0277(10)  -.0004(7)  .0018(8)  .0006(7)
  C3  .0235(9)  .0194(8)  .0316(10)  .0033(7)  .0027(8)  -.0008(7)
  C4  .0273(9)  .0264(9)  .0273(10)  .0022(8)  .0016(8)  -.0001(8)
  C5  .0246(9)  .0286(9)  .0220(9)  -.0008(7)  .0030(7)  -.0001(8)
  C6  .0265(9)  .0293(10)  .0307(10)  -.0007(8)  -.0003(8)  -.0008(8)
  C7  .0349(11)  .0305(11)  .0407(12)  -.0052(9)  .0012(10)  -.0002(9)
  C8  .0344(11)  .0413(12)  .0364(12)  -.0128(10)  .0011(10)  .0003(10)
  C9  .0237(10)  .0521(14)  .0370(11)  -.0041(9)  .0030(9)  .0026(11)
  C10  .0263(10)  .0369(12)  .0376(11)  .0049(9)  .0045(9)  -.0005(10)
  C11  .0294(10)  .0309(10)  .0544(15)  -.0021(8)  -.0071(10)  -.0007(10)
  C12  .0444(12)  .0318(10)  .0279(11)  -.0048(9)  .0011(9)  .0024(9)
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 . 1.6781(19) yes
  O1 N2 . 1.277(2) ?
  O2 N2 . 1.261(2) ?
  O3 C4 . 1.212(2) ?
  N1 C1 . 1.367(3) yes
  N1 C4 . 1.394(3) yes
  N1 H1 .  .88(2) ?
  N2 C2 . 1.368(2) yes
  N3 C3 . 1.310(3) yes
  N3 C11 . 1.452(3) ?
  N3 H3 .  .87(3) ?
  N4 C3 . 1.310(3) yes
  N4 C12 . 1.464(3) ?
  N4 H4 .  .84(3) ?
  C1 C2 . 1.435(3) yes
  C2 C3 . 1.490(3) yes
  C4 C5 . 1.489(3) ?
  C5 C6 . 1.388(3) ?
  C5 C10 . 1.400(3) ?
  C6 C7 . 1.388(3) ?
  C6 H6 .  .9500 ?
  C7 C8 . 1.392(3) ?
  C7 H7 .  .9500 ?
  C8 C9 . 1.379(3) ?
  C8 H8 .  .9500 ?
  C9 C10 . 1.383(3) ?
  C9 H9 .  .9500 ?
  C10 H10 .  .9500 ?
  C11 H111 .  .9800 ?
  C11 H112 .  .9800 ?
  C11 H113 .  .9800 ?
  C12 H121 .  .9800 ?
  C12 H122 .  .9800 ?
  C12 H123 .  .9800 ?