N-[4-(Dimethyl­amino)­benzyl­idene]-4H-1,2,4-triazol-4-amine

Hui-Liang Zhou; Xiao-Min Zhang

doi:10.1107/S1600536812014511

. 2012 Apr 13;68(Pt 5):o1343. doi: 10.1107/S1600536812014511

N-[4-(Dimethylamino)benzylidene]-4H-1,2,4-triazol-4-amine

Hui-Liang Zhou ^a,^*, Xiao-Min Zhang ^a

PMCID: PMC3344478 PMID: 22590240

Abstract

The title compound, C₁₁H₁₃N₅, is a Schiff base synthesized by the reaction of 4-amino-4H-1,2,4-triazole and 4-(dimethylamino)benzaldehyde. The dihedral angle between the benzene and triazole rings is 43.09 (11)°. The crystal structure displays weak C—H⋯N interactions.

Related literature

For the biological activity of triazole derivatives, see: Modzelewska & Kalabun (1999 ▶); Rollas et al. (1993 ▶); Todoulou et al. (1994 ▶); Demirbas et al. (2002 ▶); Kahveci et al. (2003 ▶). For 4-amino-1,2,4-triazole Schiff bases, see: Desenko & Khim (1995 ▶); Kargin et al. (1988 ▶).

Experimental

Crystal data

C₁₁H₁₃N₅
M _r = 215.26
Monoclinic,
a = 10.3665 (16) Å
b = 11.1585 (19) Å
c = 9.5248 (12) Å
β = 90.257 (1)°
V = 1101.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.52 × 0.15 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.957, T _max = 0.991
5465 measured reflections
1940 independent reflections
1184 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.119
S = 1.00
1940 reflections
148 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014511/ff2062sup1.cif

e-68-o1343-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014511/ff2062Isup2.hkl

e-68-o1343-Isup2.hkl^{(95.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812014511/ff2062Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N4ⁱ	0.93	2.57	3.448 (3)	157
C2—H2⋯N2ⁱⁱ	0.93	2.43	3.284 (3)	152
C11—H11B⋯N1ⁱⁱⁱ	0.96	2.60	3.543 (3)	166

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

We thank the Instrumental Analysis Center of LiaoCheng University for the data collection on the Bruker SMART CCD facility.

supplementary crystallographic information

Comment

1,2,4-Triazole and their derivatives have been used as starting materials for synthesis of many heterocycles. The aroyl Schiff bases of 4-amino-1,2,4-triazole have received considerable attention over the past few decades (Desenko et al., 1995; Kargin et al., 1988; Modzelewska & Kalabun, 1999). In recent years, various 1,2,4-triazoles and their derivatives have been found to be associated with diverse pharmacological activities such as anticonvulsant, antifungal, anticancer, anti-inflammatory and antibacterial (Rollas et al., 1993; Todoulou et al., 1994). The present X-ray crystal structure analysis was undertaken in order to study the stereochemistry and crystal packing of the title compound (I).

The molecular structure and the atom-numbering scheme of the title compound are shown in Fig. 1. In the molecule, all bond lengths and angles are normal. As shown in Fig 1, the title compound is composed of two planar segments. One segment is a triazole ring, which is contains N3, C1, N2, C2, N1, and another segment is a benzene ring. The dihedral angle between the two planar segments is 43.09 (11)°. In the triazole ring, the N1=C2 and N2=C1 bonds display double-bond character, with bond distances of 1.303 (3) and 1.295 (2) Å, respectively.

Experimental

A mixture of 4-amino-4H-1,2,4-triazole 1 (0.51 g, 6 mmol) and 4-Dimethylaminobenzaldehyde (0.85 g, 6 mmol) was reacted in 40 ml ethanol at 353 K for 0.3 h. Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of the ethanol solution.