Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.003 Å; R factor = 0.045; wR factor = 0.126; data-to-parameter ratio = 17.7.The molecular structure of the title compound, C 11 H 13 N 3 S, is not planar: the maximum deviation from the mean plane of the non-H atoms is 0.521 (2) Å for an aliphatic C atom, which corresponds to an envelope conformation for the nonaromatic ring. The hydrazinecarbothioamide substituent and the benzene ring have maximum deviations from the mean planes through the non-H atoms of 0.0288 (16) and 0.0124 (27) Å , respectively, and the dihedral angle between the two planes is 8.84 (13) . In the crystal, molecules are linked into chains along [110] by pairs of N-HÁ Á ÁS hydrogen bonds between molecules related by centres of symmetry. Related literature

Key indicators: single-crystal X-ray study; T = 200 K; mean (C-C) = 0.002 Å; R factor = 0.036; wR factor = 0.100; data-to-parameter ratio = 15.9.In the title compound, C 9 H 11 N 3 S, there is an intramolecular O-HÁ Á ÁO hydrogen bond involving the OH group and the adjacent methoxy O atom. The molecule is essentially planar, with the maximum deviation from the mean plane of the non-H atoms being 0.1127 (14) Å for the methyl C atom. In the crystal, molecules are connected via centrosymmetric pairs of N-HÁ Á ÁS and O-HÁ Á ÁO hydrogen bonds into a twodimensional network parallel to (103). Related literatureFor the in vitro antimalarial and antitubercular activity of hydroxy-methoxybenzaldehyde thiosemicarbazone derivatives, see: Khanye et al. (2011). For the first report of the synthesis, see: Freund & Schander (1902). For the synthesis and crystal structure of an isomer of the title compound, see: Hao (2010). ExperimentalCrystal data

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In the title compound, C15H15N3O2S, the central C—N—N—C unit has an anti conformation [torsion angle = −170.17 (15)°]. The phenyl substituent is oriented perpendicular to this unit [dihedral angle of 89.2 (1)°], whereas the substituted ring is rotated out of this plane by only 18.86 (17)°. In the crystal, mol­ecules are linked by pairs of N—H⋯S hydrogen bonds into inversion dimers that are further connected via N—H⋯O and O—H⋯S hydrogen bonds into a three-dimensional network.

Key indicators: single-crystal X-ray study; T = 200 K; mean (C-C) = 0.003 Å; disorder in main residue; R factor = 0.041; wR factor = 0.114; data-to-parameter ratio = 15.3.There are two independent molecules in the asymmetric unit of the title compound, C 12 H 15 N 3 S, both of which display disorder of several C atoms in the N-bound ring (occupancy ratios of 0.75:0.25 in the first independent molecule and 0.50:0.50 in the second) with the methyl H atoms also being disordered in the first molecule (occupancy ratio of 0.70:0.30). The planes of the benzene ring and the N-N-C-N fragment make dihedral angles of 12.92 (14) in the first independent molecule and 7.60 (13) in the second. In the crystal, molecules are linked by weak N-HÁ Á ÁS hydrogen bonds into chains along the a-axis direction. The crystal packing ressembles a herringbone arrangement. Related literature