3,5-Bis(4-methoxy­phen­yl)-1H-1,2,4-triazole monohydrate

Hai-Ying Wang; Jian-Ping Ma; Ru-Qi Huang; Yu-Bin Dong

doi:10.1107/S160053680901695X

. 2009 May 14;65(Pt 6):o1260. doi: 10.1107/S160053680901695X

3,5-Bis(4-methoxyphenyl)-1H-1,2,4-triazole monohydrate

Hai-Ying Wang ^a, Jian-Ping Ma ^a, Ru-Qi Huang ^a, Yu-Bin Dong ^a,^*

PMCID: PMC2969559 PMID: 21583125

Abstract

In the title compound, C₁₆H₁₅N₃O₂·H₂O, the two benzene rings and the triazole ring lie almost in the same plane, the triazole ring forming dihedral angles of 5.07 (9) and 5.80 (8)° with the benzene rings. In the crystal, there are three relatively strong intermolecular O—H⋯N and N—H⋯O hydrogen bonds, which lead to the formation of a one-dimensional double chain running parallel to the a axis. Weak π—π interactions between the benzene rings of neighboring chains with a centroid–centroid distance of 3.893 (4) Å result in the formation of layers parallel to the ac plane.

Related literature

For the biological activity and pharmaceutical applications of compounds containing triazole subunits, see: Chai et al. (2009 ▶); Nadkarni et al. (2001 ▶); Zhan & Lou (2007 ▶). For triazole ring bond-length data, see; Claramunt et al. (2001 ▶); Zhou et al. (2001 ▶); John (1998 ▶).

Experimental

Crystal data

C₁₆H₁₅N₃O₂·H₂O
M _r = 299.33
Triclinic,
a = 6.9948 (18) Å
b = 11.125 (3) Å
c = 11.184 (3) Å
α = 110.603 (4)°
β = 107.932 (3)°
γ = 95.690 (4)°
V = 753.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.40 × 0.20 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
3854 measured reflections
2651 independent reflections
1993 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.134
S = 1.05
2651 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 datablocks I, global. DOI: 10.1107/S160053680901695X/zl2201sup1.cif

e-65-o1260-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901695X/zl2201Isup2.hkl

e-65-o1260-Isup2.hkl^{(130.2KB, 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
O3—H3A⋯N1	0.97	1.96	2.902 (2)	164
N2—H2⋯O3ⁱ	0.86	1.90	2.753 (2)	170
O3—H3B⋯N3ⁱⁱ	0.96	1.97	2.885 (2)	159

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

Acknowledgments

The authors thank the National Natural Science Foundation of China (grant Nos. 20871076 and 20671060), the PhD Programs Foundation of the Ministry of Education of China (grant No. 200804450001) and the Shandong Natural Science Foundation (grant No. JQ200803) for support.

supplementary crystallographic information

Comment

During the past decades, compounds containing triazole subunits have been intensively studied due to their diverse biological activities, such as antibacterial, antitumor, etc. and have become a central focus in the study of agricultural and medicinal chemicals (Chai et al., 2009; Nadkarni et al., 2001; Zhan et al., 2007). In a search for more effective antibacterial compounds, we have synthesized the title compound and determined its structure.

The molecular structure of the title compound is shown in Fig. 1. The two benzene rings and the triazole ring almost lie in the same plane. The corresponding dihedral angles of each benzene ring with the triazole ring are 5.07 (9) (between C2–C7 and N1–N3/C8/C9) and 5.80 (8)° (between N1–N3/C8/C9 and C10–C15), respectively. The bond lengths of the triazole ring are very similar to other 1H-1,2,4-triazole derivatives (Claramunt et al., 2001; Zhou et al., 2001). C8—N3 (1.365 (2) Å) and N1—N2 (1.359 (2) Å) are typical for carbon-nitrogen single bonds and nitrogen-nitrogen single bonds, and C8—N1 (1.323 (2) Å) and C9—N3 (1.330 (2) Å) correspond to typical carbon-nitrogen double bonds (John, 1998). C9—N2 (1.333 (2) Å) is a carbon-nitrogen single bond, but the bond length is markedly shorter than usual carbon-nitrogen single bonds and close to a double bond due to its conjugation with the C9—N3 double bond.

The packing of the molecules in the crystal structure is stabilized through N—H···O, O—H···O and π—π interactions. Water molecules act both as hydrogen-acceptor and as hydrogen-donor which leads to the formation of a one dimensional double chain running parallel to the a axis (Fig. 2, Table 1). The ring made up of C10 to C15 (with the centroid Cg1) is parallel to its symmetry related counterpart with a Cg1··· Cg1ⁱⁱⁱ distance of 3.893 (4) Å [symmetry code: (iii)-x, -y, -z]. Adjacent chains are linked via these intermolecular π—π interactions between the Cg1 rings to form a two-dimentional layer parallel to the ac plane (Fig. 3).

Experimental

A mixture of 4-methoxyphenylmethylenemalononitrile (20 mmol), hydrazine dihydrochloride (20 mmol) and hydrazine hydrate (60 mmol) in ethylene glycol (10 ml) was heated to 403 K with stirring for 3–4 h. After cooling to room temperature, the reaction mixture was diluted with water (20 ml). The precipitate was filtered, washed with water, dried and purified by column chromatography on silica gel using CH₂Cl₂ as the eluent to afford a white solid after evaporation of the solvent. The white solid was dissolved in ethanol and colourless crystals of the title compound were obtained on slow evaporation of the solvent at room temperature.