#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014402.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_2014402
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2006
_journal_volume  62
_journal_page_first  o122
_journal_page_last  o124
_publ_section_title
;
Isolated molecules in
2-ethylsulfanyl-7-methyl-4-(4-methylphenyl)pyrazolo[1,5-<i>a</i>][1,3,5]\
triazine and hydrogen-bonded sheets of <i>R</i>~2~^2^(10),
<i>R</i>~2~^2^(16), <i>R</i>~4~^4^(22) and <i>R</i>~4~^4^(24) rings in
2-ethylsulfanyl-7-methyl-4-(4-nitrophenyl)pyrazolo[1,5-<i>a</i>][1,3,5]\
triazine
;
loop_
_publ_author_name
  'Insuasty, Henry'
  'Estrada, Martin'
  'Cobo, Justo'
  'Low, John N.'
  'Glidewell, Christopher'
_chemical_formula_moiety  'C14 H13 N5 O2 S'
_chemical_formula_sum  'C14 H13 N5 O2 S'
_chemical_formula_iupac  'C14 H13 N5 O2 S'
_chemical_formula_weight  315.35
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  7.9401(2)
_cell_length_b  8.8642(3)
_cell_length_c  11.3717(4)
_cell_angle_alpha  68.7710(17)
_cell_angle_beta  85.792(2)
_cell_angle_gamma  72.214(2)
_cell_volume  709.77(4)
_cell_formula_units_Z  2
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.476
_diffrn_ambient_temperature  120(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
  S S2 0.65933(6) 0.79303(6) 0.75064(4) 0.02523(15) Uani d . 1 . .
  O O441 0.2715(2) 0.91128(19) 0.00481(15) 0.0514(5) Uani d . 1 . .
  O O442 0.37066(17) 0.65981(17) -0.00215(12) 0.0306(3) Uani d . 1 . .
  N N1 0.87188(19) 0.48893(18) 0.75728(13) 0.0209(3) Uani d . 1 . .
  N N3 0.67349(19) 0.66664(18) 0.57816(13) 0.0197(3) Uani d . 1 . .
  N N5 0.85634(18) 0.40828(17) 0.57876(13) 0.0179(3) Uani d . 1 . .
  N N6 0.93182(19) 0.27691(18) 0.53614(13) 0.0209(3) Uani d . 1 . .
  N N44 0.3581(2) 0.7613(2) 0.04943(14) 0.0251(4) Uani d . 1 . .
  C C2 0.7501(2) 0.6287(2) 0.69349(16) 0.0195(4) Uani d . 1 . .
  C C4 0.7250(2) 0.5561(2) 0.52146(16) 0.0179(4) Uani d . 1 . .
  C C7 1.0470(2) 0.1625(2) 0.63002(17) 0.0222(4) Uani d . 1 . .
  C C8 1.0480(2) 0.2153(2) 0.73220(17) 0.0223(4) Uani d . 1 . .
  C C9 0.9272(2) 0.3737(2) 0.69906(16) 0.0193(4) Uani d . 1 . .
  C C21 0.7724(2) 0.7145(2) 0.90290(16) 0.0230(4) Uani d . 1 . .
  C C22 0.9584(2) 0.7286(2) 0.89856(18) 0.0282(4) Uani d . 1 . .
  C C41 0.6352(2) 0.5985(2) 0.39846(15) 0.0175(4) Uani d . 1 . .
  C C42 0.5003(2) 0.7535(2) 0.35603(17) 0.0229(4) Uani d . 1 . .
  C C43 0.4101(2) 0.8065(2) 0.24201(17) 0.0233(4) Uani d . 1 . .
  C C44 0.4540(2) 0.7025(2) 0.17160(16) 0.0202(4) Uani d . 1 . .
  C C45 0.5829(2) 0.5471(2) 0.21184(16) 0.0218(4) Uani d . 1 . .
  C C46 0.6751(2) 0.4955(2) 0.32572(16) 0.0213(4) Uani d . 1 . .
  C C71 1.1603(3) 0.0013(2) 0.61612(19) 0.0298(4) Uani d . 1 . .
  H H8 1.1179 0.1540 0.8086 0.027 Uiso calc R 1 . .
  H H21A 0.7014 0.7780 0.9548 0.028 Uiso calc R 1 . .
  H H21B 0.7782 0.5938 0.9457 0.028 Uiso calc R 1 . .
  H H22A 1.0314 0.6632 0.8498 0.042 Uiso calc R 1 . .
  H H22B 1.0097 0.6837 0.9847 0.042 Uiso calc R 1 . .
  H H22C 0.9545 0.8479 0.8584 0.042 Uiso calc R 1 . .
  H H42 0.4707 0.8227 0.4062 0.027 Uiso calc R 1 . .
  H H43 0.3197 0.9123 0.2126 0.028 Uiso calc R 1 . .
  H H45 0.6081 0.4768 0.1625 0.026 Uiso calc R 1 . .
  H H46 0.7656 0.3897 0.3543 0.026 Uiso calc R 1 . .
  H H71A 1.0848 -0.0626 0.6057 0.045 Uiso calc R 1 . .
  H H71B 1.2383 -0.0669 0.6917 0.045 Uiso calc R 1 . .
  H H71C 1.2320 0.0277 0.5418 0.045 Uiso calc R 1 . .
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
  S2 0.0272(3) 0.0242(3) 0.0232(3) -0.00026(19) -0.00623(18) -0.01183(19)
  O441 0.0752(12) 0.0289(8) 0.0364(9) 0.0093(8) -0.0328(8) -0.0099(7)
  O442 0.0321(7) 0.0384(8) 0.0255(7) -0.0072(6) -0.0053(6) -0.0177(6)
  N1 0.0224(8) 0.0211(8) 0.0185(8) -0.0055(6) -0.0018(6) -0.0069(6)
  N3 0.0211(7) 0.0192(8) 0.0185(7) -0.0052(6) -0.0015(6) -0.0068(6)
  N5 0.0193(7) 0.0159(7) 0.0177(7) -0.0040(6) -0.0019(6) -0.0055(6)
  N6 0.0213(8) 0.0171(7) 0.0229(8) -0.0021(6) -0.0020(6) -0.0082(6)
  N44 0.0267(8) 0.0266(9) 0.0207(8) -0.0055(7) -0.0041(6) -0.0079(7)
  C2 0.0205(9) 0.0211(9) 0.0182(9) -0.0077(7) -0.0003(7) -0.0070(7)
  C4 0.0175(8) 0.0165(8) 0.0189(9) -0.0059(7) 0.0008(7) -0.0045(7)
  C7 0.0203(9) 0.0201(9) 0.0242(9) -0.0060(7) -0.0022(7) -0.0052(7)
  C8 0.0229(9) 0.0199(9) 0.0204(9) -0.0041(7) -0.0055(7) -0.0037(7)
  C9 0.0210(9) 0.0208(9) 0.0165(8) -0.0085(7) -0.0013(7) -0.0047(7)
  C21 0.0273(9) 0.0244(10) 0.0175(9) -0.0051(8) -0.0009(7) -0.0094(7)
  C22 0.0258(10) 0.0284(10) 0.0294(10) -0.0037(8) -0.0048(8) -0.0119(8)
  C41 0.0179(8) 0.0170(8) 0.0173(8) -0.0070(7) -0.0001(7) -0.0042(7)
  C42 0.0257(9) 0.0199(9) 0.0230(9) -0.0040(8) -0.0039(7) -0.0091(7)
  C43 0.0249(9) 0.0174(9) 0.0241(10) -0.0007(7) -0.0066(7) -0.0065(7)
  C44 0.0220(9) 0.0224(9) 0.0158(8) -0.0076(7) -0.0027(7) -0.0048(7)
  C45 0.0231(9) 0.0237(9) 0.0201(9) -0.0059(8) 0.0000(7) -0.0100(7)
  C46 0.0209(9) 0.0201(9) 0.0210(9) -0.0035(7) -0.0021(7) -0.0068(7)
  C71 0.0315(10) 0.0203(10) 0.0328(11) 0.0009(8) -0.0059(8) -0.0097(8)
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 C2 . 1.310(2) no
  N1 C9 . 1.360(2) no
  C2 N3 . 1.370(2) no
  C2 S2 . 1.7432(18) no
  S2 C21 . 1.8063(18) no
  C21 C22 . 1.515(3) no
  C21 H21A . 0.99 no
  C21 H21B . 0.99 no
  C22 H22A . 0.98 no
  C22 H22B . 0.98 no
  C22 H22C . 0.98 no
  N3 C4 . 1.310(2) no
  C4 N5 . 1.370(2) no
  C4 C41 . 1.486(2) no
  C41 C46 . 1.397(2) no
  C41 C42 . 1.402(2) no
  C42 C43 . 1.380(2) no
  C42 H42 . 0.95 no
  C43 C44 . 1.382(2) no
  C43 H43 . 0.95 no
  C44 C45 . 1.380(3) no
  C44 N44 . 1.473(2) no
  N44 O442 . 1.2175(19) no
  N44 O441 . 1.225(2) no
  C45 C46 . 1.388(2) no
  C45 H45 . 0.95 no
  C46 H46 . 0.95 no
  N5 N6 . 1.3747(19) no
  N5 C9 . 1.409(2) no
  N6 C7 . 1.341(2) no
  C7 C8 . 1.403(3) no
  C7 C71 . 1.494(2) no
  C71 H71A . 0.98 no
  C71 H71B . 0.98 no
  C71 H71C . 0.98 no
  C8 C9 . 1.371(2) no
  C8 H8 . 0.95 no