data_2200326
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o547
_journal_page_last  o549
_publ_section_title
;
4-Amino-5-methyl-1,2,4-triazole-3-thione derivative of
4-[2-(2-hydroxyethyl)methylamino]benzaldehyde
;
loop_
_publ_author_name
  'Ji Wu'
  'Yu-Peng Tian'
  'Fu-Xin Xie'
  'Suchada Chantrapromma'
  'Hoong-Kun Fun'
  'Ibrahim Abdul Razak'
_chemical_formula_moiety  'C13 H17 N5 O S'
_chemical_formula_sum  'C13 H17 N5 O S'
_chemical_formula_iupac  'C13 H17 N5 O S'
_chemical_formula_weight  291.38
_chemical_melting_point  448.6
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  10.7043(2)
_cell_length_b  10.7230(2)
_cell_length_c  13.9487(3)
_cell_angle_alpha  103.3520(10)
_cell_angle_beta  111.8350(10)
_cell_angle_gamma  92.5190(10)
_cell_volume  1431.01(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.352
_diffrn_ambient_temperature  293(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  .69145(7)  .69502(8)  .72016(6)  .0527(2) Uani d . 1 . . S
  O1A  .0703(2)  .66841(19)  -.05338(14)  .0466(5) Uani d . 1 . . O
  N1A  .9506(2)  .8044(2)  .79000(16)  .0448(6) Uani d . 1 . . N
  H1AA  .9771  .7673  .8412  .054 Uiso calc R 1 . . H
  N3A  .8274(2)  .8632(2)  .65341(15)  .0367(5) Uani d . 1 . . N
  N4A  .7339(2)  .8770(2)  .55563(16)  .0416(5) Uani d . 1 . . N
  N5A  .2095(2)  .8870(2)  .13868(17)  .0468(6) Uani d . 1 . . N
  N2A 1.0380(2)  .8868(2)  .77290(17)  .0462(6) Uani d . 1 . . N
  C1A 1.0061(3) 1.0107(3)  .6388(2)  .0548(8) Uani d . 1 . . C
  H1AB 1.0979 1.0505  .6837  .082 Uiso calc R 1 . . H
  H1AC  .9480 1.0764  .6297  .082 Uiso calc R 1 . . H
  H1AD 1.0023  .9631  .5701  .082 Uiso calc R 1 . . H
  C2A  .9604(3)  .9215(3)  .6893(2)  .0396(6) Uani d . 1 . . C
  C3A  .8207(3)  .7870(2)  .72023(19)  .0380(6) Uani d . 1 . . C
  C4A  .6090(3)  .8385(3)  .5280(2)  .0432(7) Uani d . 1 . . C
  H4AA  .5806  .8039  .5730  .052 Uiso calc R 1 . . H
  C5A  .5090(3)  .8482(2)  .4255(2)  .0389(6) Uani d . 1 . . C
  C6A  .3733(3)  .8004(3)  .3942(2)  .0449(7) Uani d . 1 . . C
  H6AA  .3479  .7614  .4385  .054 Uiso calc R 1 . . H
  C7A  .2744(3)  .8092(3)  .2985(2)  .0439(7) Uani d . 1 . . C
  H7AA  .1848  .7734  .2789  .053 Uiso calc R 1 . . H
  C8A  .3072(3)  .8709(2)  .23119(19)  .0379(6) Uani d . 1 . . C
  C9A  .4452(3)  .9178(3)  .2627(2)  .0439(7) Uani d . 1 . . C
  H9AA  .4713  .9577  .2191  .053 Uiso calc R 1 . . H
  C10A  .5424(3)  .9058(3)  .3567(2)  .0444(7) Uani d . 1 . . C
  H10A  .6329  .9371  .3748  .053 Uiso calc R 1 . . H
  C11A  .0683(3)  .8309(3)  .1005(2)  .0491(7) Uani d . 1 . . C
  H11A  .0121  .8797  .0547  .059 Uiso calc R 1 . . H
  H11B  .0431  .8399  .1615  .059 Uiso calc R 1 . . H
  C12A  .0381(3)  .6901(3)  .0393(2)  .0490(7) Uani d . 1 . . C
  H12A  .0900  .6401  .0861  .059 Uiso calc R 1 . . H
  H12B  -.0577  .6597  .0173  .059 Uiso calc R 1 . . H
  C13A  .2454(3)  .9634(3)  .0766(2)  .0532(8) Uani d . 1 . . C
  H13A  .2852 1.0494  .1212  .080 Uiso calc R 1 . . H
  H13B  .1651  .9676  .0170  .080 Uiso calc R 1 . . H
  H13C  .3095  .9238  .0508  .080 Uiso calc R 1 . . H
  S1B 1.28467(8)  .16528(9)  .92159(7)  .0663(3) Uani d . 1 . . S
  O1B  .6498(2)  .1485(2)  .16659(16)  .0638(6) Uani d . 1 . . O
  N1B 1.5501(2)  .2721(2) 1.00488(17)  .0444(6) Uani d . 1 . . N
  H1BA 1.5738  .2353 1.0564  .053 Uiso calc R 1 . . H
  N2B 1.6408(2)  .3501(2)  .98786(17)  .0438(6) Uani d . 1 . . N
  N3B 1.4323(2)  .3373(2)  .87137(15)  .0369(5) Uani d . 1 . . N
  N4B 1.3312(2)  .3451(2)  .77424(16)  .0407(5) Uani d . 1 . . N
  N5B  .7576(2)  .4000(2)  .42453(18)  .0510(6) Uani d . 1 . . N
  C1B 1.6141(3)  .4734(3)  .8523(2)  .0546(8) Uani d . 1 . . C
  H1BB 1.7113  .4944  .8868  .082 Uiso calc R 1 . . H
  H1BC 1.5737  .5515  .8581  .082 Uiso calc R 1 . . H
  H1BD 1.5888  .4296  .7781  .082 Uiso calc R 1 . . H
  C2B 1.5655(3)  .3879(3)  .9047(2)  .0385(6) Uani d . 1 . . C
  C3B 1.4214(3)  .2585(3)  .9339(2)  .0408(6) Uani d . 1 . . C
  C4B 1.2201(2)  .3737(2)  .7832(2)  .0365(6) Uani d . 1 . . C
  H4BA 1.2163  .3938  .8505  .044 Uiso calc R 1 . . H
  C5B 1.1004(2)  .3753(2)  .6900(2)  .0351(6) Uani d . 1 . . C
  C6B  .9942(3)  .4377(3)  .7029(2)  .0404(6) Uani d . 1 . . C
  H6BA  .9995  .4744  .7719  .049 Uiso calc R 1 . . H
  C7B  .8813(3)  .4465(3)  .6165(2)  .0416(6) Uani d . 1 . . C
  H7BA  .8130  .4905  .6279  .050 Uiso calc R 1 . . H
  C8B  .8687(2)  .3899(2)  .5116(2)  .0390(6) Uani d . 1 . . C
  C9B  .9744(3)  .3230(3)  .4989(2)  .0437(7) Uani d . 1 . . C
  H9BA  .9677  .2820  .4304  .052 Uiso calc R 1 . . H
  C10B 1.0866(3)  .3174(2)  .5856(2)  .0403(6) Uani d . 1 . . C
  H10B 1.1554  .2738  .5747  .048 Uiso calc R 1 . . H
  C11B  .7401(3)  .3393(3)  .3140(2)  .0516(8) Uani d . 1 . . C
  H11C  .8284  .3417  .3095  .062 Uiso calc R 1 . . H
  H11D  .6858  .3883  .2674  .062 Uiso calc R 1 . . H
  C12B  .6721(3)  .2012(3)  .2762(2)  .0499(7) Uani d . 1 . . C
  H12C  .7290  .1503  .3195  .060 Uiso calc R 1 . . H
  H12D  .5858  .1976  .2841  .060 Uiso calc R 1 . . H
  C13B  .6554(3)  .4782(3)  .4401(3)  .0634(9) Uani d . 1 . . C
  H13E  .6992  .5624  .4865  .095 Uiso calc R 1 . . H
  H13F  .6056  .4370  .4719  .095 Uiso calc R 1 . . H
  H13G  .5940  .4868  .3721  .095 Uiso calc R 1 . . H
  H1AE  .159(4)  .666(4)  -.039(3)  .100(14) Uiso d . 1 . . H
  H1BE  .695(6)  .083(6)  .155(5)  .21(3) 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
  S1A  .0453(5)  .0619(5)  .0566(5)  .0056(3)  .0192(4)  .0282(4)
  O1A  .0347(12)  .0619(12)  .0345(10)  .0090(9)  .0045(8)  .0120(9)
  N1A  .0418(14)  .0569(14)  .0328(12)  .0039(11)  .0068(10)  .0203(11)
  N3A  .0385(13)  .0426(12)  .0271(11)  .0085(10)  .0081(9)  .0133(9)
  N4A  .0427(15)  .0466(13)  .0302(12)  .0073(10)  .0058(10)  .0146(10)
  N5A  .0462(15)  .0496(14)  .0359(13)  .0017(11)  .0032(10)  .0180(11)
  N2A  .0416(14)  .0529(14)  .0394(13)  .0005(11)  .0099(11)  .0146(11)
  C1A  .0558(19)  .0604(18)  .0485(18)  -.0009(14)  .0182(14)  .0209(15)
  C2A  .0404(16)  .0438(15)  .0313(14)  .0030(12)  .0113(12)  .0090(12)
  C3A  .0407(16)  .0407(14)  .0308(13)  .0106(11)  .0111(12)  .0100(11)
  C4A  .0438(18)  .0484(16)  .0359(15)  .0083(13)  .0118(12)  .0147(12)
  C5A  .0399(16)  .0412(14)  .0315(14)  .0067(12)  .0074(11)  .0134(11)
  C6A  .0452(18)  .0514(16)  .0399(15)  .0066(13)  .0123(13)  .0231(13)
  C7A  .0365(16)  .0507(16)  .0414(15)  .0023(12)  .0089(12)  .0181(13)
  C8A  .0392(16)  .0351(14)  .0320(14)  .0048(11)  .0061(12)  .0083(11)
  C9A  .0475(18)  .0472(16)  .0335(14)  -.0006(13)  .0104(12)  .0148(12)
  C10A  .0384(16)  .0486(16)  .0401(15)  .0006(12)  .0090(12)  .0125(13)
  C11A  .0413(18)  .0633(18)  .0389(15)  .0159(14)  .0095(13)  .0155(14)
  C12A  .0401(17)  .0605(18)  .0406(16)  .0007(13)  .0102(13)  .0134(14)
  C13A  .067(2)  .0492(17)  .0388(16)  .0110(14)  .0109(14)  .0203(14)
  S1B  .0406(5)  .0849(6)  .0817(6)  .0036(4)  .0154(4)  .0534(5)
  O1B  .0783(16)  .0664(15)  .0358(12)  .0288(12)  .0065(10)  .0167(10)
  N1B  .0327(13)  .0625(15)  .0391(13)  .0110(11)  .0078(10)  .0255(11)
  N2B  .0333(13)  .0509(14)  .0420(13)  .0077(10)  .0071(10)  .0154(11)
  N3B  .0282(12)  .0485(13)  .0315(11)  .0074(9)  .0034(9)  .0196(10)
  N4B  .0298(13)  .0522(13)  .0355(12)  .0078(10)  .0031(9)  .0193(10)
  N5B  .0411(14)  .0519(14)  .0417(14)  .0128(11)  -.0040(10)  .0113(11)
  C1B  .0411(18)  .0603(19)  .065(2)  .0050(14)  .0150(15)  .0315(16)
  C2B  .0307(15)  .0435(15)  .0388(15)  .0065(11)  .0098(12)  .0123(12)
  C3B  .0360(16)  .0504(16)  .0361(15)  .0128(12)  .0080(12)  .0209(12)
  C4B  .0323(15)  .0369(14)  .0363(14)  .0052(11)  .0063(11)  .0142(11)
  C5B  .0281(14)  .0355(13)  .0372(14)  .0031(11)  .0046(11)  .0157(11)
  C6B  .0359(16)  .0442(15)  .0373(15)  .0060(12)  .0097(12)  .0114(12)
  C7B  .0307(15)  .0444(15)  .0465(16)  .0110(11)  .0087(12)  .0160(13)
  C8B  .0276(15)  .0370(13)  .0412(15)  .0019(11)  -.0002(11)  .0129(12)
  C9B  .0401(16)  .0483(16)  .0335(14)  .0078(12)  .0047(12)  .0099(12)
  C10B  .0325(15)  .0436(15)  .0409(15)  .0091(11)  .0086(12)  .0130(12)
  C11B  .0415(17)  .0570(18)  .0476(18)  .0020(13)  .0007(13)  .0272(14)
  C12B  .0471(18)  .0550(18)  .0413(16)  .0033(13)  .0094(13)  .0152(14)
  C13B  .0422(19)  .067(2)  .065(2)  .0174(15)  -.0002(15)  .0204(17)
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
  S1A C3A . 1.663(3) yes
  O1A C12A . 1.430(3) ?
  O1A H1AE .  .90(4) ?
  N1A C3A . 1.342(3) ?
  N1A N2A . 1.380(3) ?
  N1A H1AA .  .8600 ?
  N3A C2A . 1.384(3) ?
  N3A C3A . 1.392(3) ?
  N3A N4A . 1.405(3) ?
  N4A C4A . 1.266(3) ?
  N5A C8A . 1.380(3) ?
  N5A C11A . 1.450(3) ?
  N5A C13A . 1.454(3) ?
  N2A C2A . 1.302(3) ?
  C1A C2A . 1.475(4) ?
  C1A H1AB .  .9600 ?
  C1A H1AC .  .9600 ?
  C1A H1AD .  .9600 ?
  C4A C5A . 1.462(4) ?
  C4A H4AA .  .9300 ?
  C5A C6A . 1.386(4) ?
  C5A C10A . 1.393(4) ?
  C6A C7A . 1.388(4) ?
  C6A H6AA .  .9300 ?
  C7A C8A . 1.399(4) ?
  C7A H7AA .  .9300 ?
  C8A C9A . 1.406(4) ?
  C9A C10A . 1.376(4) ?
  C9A H9AA .  .9300 ?
  C10A H10A .  .9300 ?
  C11A C12A . 1.507(4) ?
  C11A H11A .  .9700 ?
  C11A H11B .  .9700 ?
  C12A H12A .  .9700 ?
  C12A H12B .  .9700 ?
  C13A H13A .  .9600 ?
  C13A H13B .  .9600 ?
  C13A H13C .  .9600 ?
  S1B C3B . 1.666(3) yes
  O1B C12B . 1.425(3) ?
  O1B H1BE .  .89(6) ?
  N1B C3B . 1.342(3) ?
  N1B N2B . 1.375(3) ?
  N1B H1BA .  .8600 ?
  N2B C2B . 1.308(3) ?
  N3B C2B . 1.366(3) ?
  N3B C3B . 1.378(3) ?
  N3B N4B . 1.408(3) ?
  N4B C4B . 1.283(3) ?
  N5B C8B . 1.378(3) ?
  N5B C13B . 1.456(4) ?
  N5B C11B . 1.465(3) ?
  C1B C2B . 1.481(4) ?
  C1B H1BB .  .9600 ?
  C1B H1BC .  .9600 ?
  C1B H1BD .  .9600 ?
  C4B C5B . 1.451(3) ?
  C4B H4BA .  .9300 ?
  C5B C6B . 1.392(3) ?
  C5B C10B . 1.393(3) ?
  C6B C7B . 1.379(3) ?
  C6B H6BA .  .9300 ?
  C7B C8B . 1.401(4) ?
  C7B H7BA .  .9300 ?
  C8B C9B . 1.410(4) ?
  C9B C10B . 1.367(3) ?
  C9B H9BA .  .9300 ?
  C10B H10B .  .9300 ?
  C11B C12B . 1.504(4) ?
  C11B H11C .  .9700 ?
  C11B H11D .  .9700 ?
  C12B H12C .  .9700 ?
  C12B H12D .  .9700 ?
  C13B H13E .  .9600 ?
  C13B H13F .  .9600 ?
  C13B H13G .  .9600 ?