3,5-Bis(4-meth­oxy­phen­yl)-4H-1,2,4-triazol-4-amine

Hui Yang; Zhan-Dong Huang; Guang Yang; Seik Weng Ng

doi:10.1107/S1600536810030898

. 2010 Aug 11;66(Pt 9):o2236. doi: 10.1107/S1600536810030898

3,5-Bis(4-methoxyphenyl)-4H-1,2,4-triazol-4-amine

Hui Yang ^a, Zhan-Dong Huang ^a, Guang Yang ^a, Seik Weng Ng ^b,^*

PMCID: PMC3008083 PMID: 21588604

Abstract

The title compound, C₁₆H₁₆N₄O₂, crystallizes with two molecules in the asymmetric unit, which are related by a non-crystallographic centre of inversion. The phenylene rings are twisted out of the mean plane of the triazole ring by 19.3 (1) and 21.4 (1)° for one independent molecule and by 16.3 (1) and 18.1 (1)° for the other molecule. In the crystal, adjacent molecules are linked by amine–triazole N—H⋯N hydrogen bonds, forming chains running along the a axis.

Related literature

For the synthesis, see: Bentiss et al. (1999 ▶). For the two polymorphs of 3,5-diphenyl-1,2,4-triazol-4-amine, see: Ikemi et al. (2002 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C₁₆H₁₆N₄O₂
M _r = 296.33
Monoclinic,
a = 11.2232 (9) Å
b = 7.2386 (6) Å
c = 17.9766 (14) Å
β = 107.147 (1)°
V = 1395.51 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.40 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
12717 measured reflections
3459 independent reflections
2709 reflections with I > 2σ(I)
R _int = 0.086

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.147
S = 1.06
3459 reflections
417 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030898/bt5318sup1.cif

e-66-o2236-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030898/bt5318Isup2.hkl

e-66-o2236-Isup2.hkl^{(169.6KB, hkl)}

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
N1—H1⋯N8	0.86 (4)	2.20 (2)	3.027 (5)	162 (4)
N5—H3⋯N4ⁱ	0.86 (3)	2.18 (3)	3.029 (5)	166 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the National Science Foundation of China (No. J0830412) and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The compound was intended for the synthesis of gold complexes as the two nitrogen atoms of the ring can possibly give rise to triangular-shaped trinuclear compounds. The parent compound, 3,5-diphenyl-1,2,4-triazol-4-amine, which exists in two polymorphic forms (Ikemi et al., 2002; Zhang et al., 2009), furnishes a number of metal derivatives. In the methoxy-substituted derivative (Scheme I), the five-membered triazole ring is planar but the phenylene rings are twisted out of the mean plane [19.3 (1), 21.4 (1) °; 16.3 (1), 18.1 (1) °] in the two indepedent molecules (Fig. 1). The twist angles are smaller than those noted in the parent compound. Adjacent molecules are linked by N–H_amino···N_triazole hydrogen bonds to form chain running along the a-axis (Fig. 2).

Experimental

The compound was synthesized by using a literature method (Bentiss et al., 1999), and crystals were obtained upon recrystallzation from aqueous methanol.