2-Phen­oxy-1,2,4-triazolo[1,5-a]quinazol­in-5(4H)-one

Rashad Al-Salahi; Lolak Nabih; Mohamed Al-Omar; Seik Weng Ng

doi:10.1107/S1600536812021782

. 2012 May 19;68(Pt 6):o1808. doi: 10.1107/S1600536812021782

2-Phenoxy-1,2,4-triazolo[1,5-a]quinazolin-5(4H)-one

Rashad Al-Salahi ^a, Lolak Nabih ^b, Mohamed Al-Omar ^a, Seik Weng Ng ^c,^d,^*

PMCID: PMC3379382 PMID: 22719580

Abstract

The triazoloquinazole ring system in the title compound, C₁₅H₁₀N₄O₂ is approximately planar (r.m.s. deviation = 0.035 Å). The phenyl ring of the phenoxy substitutent is aligned at 59.3 (1)° with respect to this ring system. In the crystal, two molecules are linked about a center of inversion by a pair of N—H⋯O hydrogen bonds, generating a dimer.

Related literature

The synthesis was based on theat of a similar compound; see: Al-Salahi & Geffken (2011 ▶). graphic file with name e-68-o1808-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₀N₄O₂
M _r = 278.27
Triclinic,
a = 5.6985 (2) Å
b = 8.4328 (4) Å
c = 13.4322 (7) Å
α = 74.087 (4)°
β = 86.623 (4)°
γ = 89.284 (4)°
V = 619.66 (5) Å³
Z = 2
Cu Kα radiation
μ = 0.86 mm⁻¹
T = 294 K
0.30 × 0.30 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.783, T _max = 0.919
10219 measured reflections
2570 independent reflections
2408 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.103
S = 1.03
2570 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 datablock(s) global, I. DOI: 10.1107/S1600536812021782/bt5917sup1.cif

e-68-o1808-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021782/bt5917Isup2.hkl

e-68-o1808-Isup2.hkl^{(126.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812021782/bt5917Isup3.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
N1—H1⋯O1ⁱ	0.88 (1)	1.90 (1)	2.775 (1)	174 (1)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Research Center of the College of Pharmacy College and Deanship of Scientific Research of King Saud University, and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

supplementary crystallographic information

Comment

The procedure for the synthesis of 2-(methylsulfanyl)-[1,2,4]triazolo[1,5-a]quinazolin-5-one uses dimethyl N-cyanodithioimidocarbonate as one of the reactants (Al-Salahi & Geffken, 2011). The title phenoxy-substituted analog (Scheme I) is obtained with diphenyl N-cyanodithioimidocarbonate instead. The triazoloquinazole fused-ring system of C₁₅H₁₀N₄O₂ is planar. The phenyl ring of the phenoxy substitutent is aligned at 59.3 (1) ° with respect to this ring system. Two molecules are linked about a center of inversion by N–H···O hydrogen bonds to generate a dimer (Table 1).

Experimental

Under ice-cold conditions, 2-hydrazinobenzoic acid (10 mmol, 1.52 g) was added to a solution of diphenyl N-cyanodithioimidocarbonate (10 mmol, 2.38 g) in ethanol (20 ml). Triethylamine (30 mmol, 3.03 g) was added. The reaction mixture was stirred overnight at room temperature. Concentrated hydrochloric acid was added; the acidified mixture for heated for an hour. The mixture was poured into ice water; the solid that formed was collected and recrystallized from ethanol to give colorless crystals of 2-phenoxy-[1,2,4]triazolo[1,5-a]quinazolin-5-one. The procedure was based on that reported for 2-(methylsulfanyl)-[1,2,4]triazolo[1,5-a]quinazolin-5-one (Al-Salahi & Geffken, 2011).