5-(3-Nitrobenzyl)-1,3,4-thiadiazol-2-amine

In the title molecule, C9H8N4O2S, the dihedral angle between the thiadiazole and benzene rings is 73.92 (8)° and the thiadiazole group S atom is orientated towards the benzene ring, the central S—C—C—C torsion angle being 45.44 (18)°. In the crystal, supramolecular tapes mediated by N—H⋯N hydrogen bonds and comprising alternating eight-membered {⋯HNCN}2 and 10-membered {⋯HNH⋯NN}2 synthons are formed along [010]. The tapes are consolidated into a three-dimensional network by a combination of C—H⋯O, C—H⋯S and C—H⋯π interactions

In the title molecule, C 9 H 8 N 4 O 2 S, the dihedral angle between the thiadiazole and benzene rings is 73.92 (8) and the thiadiazole group S atom is orientated towards the benzene ring, the central S-C-C-C torsion angle being 45.44 (18) . In the crystal, supramolecular tapes mediated by N-HÁ Á ÁN hydrogen bonds and comprising alternating eight-membered {Á Á ÁHNCN} 2 and 10-membered {Á Á ÁHNHÁ Á ÁNN} 2 synthons are formed along [010]. The tapes are consolidated into a threedimensional network by a combination of C-HÁ Á ÁO, C-HÁ Á ÁS and C-HÁ Á Á interactions
The use of the EPSRC X-ray crystallographic service at the University of Southampton, England and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil).

Refinement
The C-bound H atoms were geometrically placed with C-H = 0.95-0.99 Å, and refined as riding with U iso (H) = 1.2U eq (C).
The N-bound H atoms were located from a difference map and included in the model with N-H = 0.880±0.001 Å, and with U iso (H) = 1.2U eq (N).
supplementary materials sup-2 Figures   Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.  Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.