4-Benzyl-1-p-tolyl-1H-1,2,4-triazol-5(4H)-one

Yu-Jin Zhu; Hong-Quan Duan

doi:10.1107/S1600536809002487

. 2009 Jan 23;65(Pt 2):o384. doi: 10.1107/S1600536809002487

4-Benzyl-1-p-tolyl-1H-1,2,4-triazol-5(4H)-one

Yu-Jin Zhu ^a,^b, Hong-Quan Duan ^a,^*

PMCID: PMC2968189 PMID: 21581980

Abstract

In the title compound, C₁₆H₁₅N₃O, the triazole ring makes dihedral angles of 7.08 (2) and 74.53 (3)° with the two outer aromatic rings. The crystal packing is stabilized by very short intermolecular C—H⋯O hydrogen bonds and weak π–π stacking interactions [centroid-to-centroid distance 3.632 (3) Å], resulting in the formation of zigzag chains parallel to the b axis.

Related literature

For details of the biological activity of trisubstituted triazolinones, see: Chang et al. (1993 ▶, 1994 ▶). For bond-length data, see: Allen et al. (1987 ▶). For details of synthesis, see: Theodoridis (1998 ▶).

Experimental

Crystal data

C₁₆H₁₅N₃O
M _r = 265.31
Monoclinic,
a = 4.6130 (9) Å
b = 25.488 (5) Å
c = 11.460 (2) Å
β = 96.18 (3)°
V = 1339.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 113 (2) K
0.18 × 0.04 × 0.04 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.985, T _max = 0.997
9828 measured reflections
2333 independent reflections
1998 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.150
S = 1.10
2333 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002487/hg2470sup1.cif

e-65-0o384-sup1.cif^{(18KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002487/hg2470Isup2.hkl

e-65-0o384-Isup2.hkl^{(114.7KB, 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
C9—H9⋯O1ⁱ	0.93	2.19	3.114 (2)	174

Open in a new tab

Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

4-Benzyl-1-p-tolyl-1H-1,2,4-triazol-5(4H)-one is a N-substituted triazolinone. It was reported that trisubstituted triazolinones were employed as nonpeptide angiotensin II receptor antagonists (Chang et al., 1993, 1994). In our effort to further study triazolinone derivatives as novel AII antagonists, the title compound was prepared. Here, we report the crystal structure of it.

In title compound, all bond lengths in the molecule are normal (Allen et al., 1987). The triazole ring N1–N3/C8–C9 makes dihedral angles of 7.08 (2) and 74.53 (3)° with the two phenyl rings (C1–C6, C11–C16). The relatively short distance of 3.632 (3) Å between the centroids of triazole ring N1–N3/C8–C9 and benzene ring C1–C6 [at -1 + x, y, z] indicates the presence of weak π–π interactions, The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds, linking the molecules into zigzag chains parallel to the b axis.

Experimental

1-p-Tolyl-1H-1,2,4-triazol-5(4H)one (1.75 g, 0.01 mol) was dissolved in 30 ml of acetic anhydride, 1.38 g (0.01 mol) potassium carbonate and 0.75 ml (0.01 mol) phenylmethanol were added. The solution was heated to reflux and stirred for 2 h and then cooled to room temperature. 100 ml of water was added and the deposited precipitate filtered. The precipitate was recrystallized with aetone and dried to give 4-benzyl-1-p-tolyl-1H-1,2,4-triazol-5(4H)one as a colorless power (2.40 g, yield 90.5%) (Theodoridis, 1998). Crystals suitable for X-ray diffraction were obtained through slow evaporation of the solution of the title compound in dichloromethane and ethyl acetate (v/v 1:1).