3-(4-Chloro­phen­yl)quinazolin-4(3H)-one

M Gnana Ruba Priya; T Srinivasan; K Girija; N Ravi Chandran; D Velmurugan

doi:10.1107/S1600536811030935

. 2011 Aug 11;67(Pt 9):o2310. doi: 10.1107/S1600536811030935

3-(4-Chlorophenyl)quinazolin-4(3H)-one

M Gnana Ruba Priya ^a, T Srinivasan ^b, K Girija ^c, N Ravi Chandran ^d, D Velmurugan ^b,^*

PMCID: PMC3200588 PMID: 22058942

Abstract

In the title compound, C₁₄H₉ClN₂O, the quinazoline unit is essentially planar, with a mean deviation from the least-squares plane defined by the ten constituent ring atoms of 0.027 (2) Å. The dihedral angle between the mean plane of the quinazoline ring system and the 4-chlorophenyl ring is 44.63 (5)°. In the crystal, molecules are linked by intermolecular C—H⋯N and C—H⋯O hydrogen bonds, forming infinite chains of alternating R₂²(6) dimers and R₂²(14) ring motifs.

Related literature

For the synthesis of the title compound, see: Priya et al. (2011 ▶). For related structures, see: Li & Feng (2009 ▶); Li et al. (2010 ▶). For the biological activity of quinazoline derivatives, see: Wolfe et al. (1990 ▶); Tereshima et al. (1995 ▶); Pandeya et al. (1999 ▶). For graph-set notation see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₉ClN₂O
M _r = 256.68
Monoclinic,
a = 16.9531 (8) Å
b = 3.9290 (3) Å
c = 17.2740 (8) Å
β = 91.626 (3)°
V = 1150.14 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 293 K
0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.926, T _max = 0.938
11055 measured reflections
2920 independent reflections
1870 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.133
S = 1.01
2920 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030935/lx2195sup1.cif

e-67-o2310-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030935/lx2195Isup2.hkl

e-67-o2310-Isup2.hkl^{(140.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811030935/lx2195Isup3.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
C7—H7⋯N1ⁱ	0.93	2.47	3.281 (2)	145
C13—H13⋯O1ⁱⁱ	0.93	2.37	3.145 (2)	140

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

Acknowledgments

TS and DV thank the TBI, X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and a DST inspire fellowship for financial support

supplementary crystallographic information

Comment

4(3H)-Quinazolinones are an important class of fused heterocycles with a wide range of biological activities such as anti–cancer (Wolfe et al.,1990), anti-inflammatory (Tereshima et al.,1995), anti–HIV (Pandeya et al., 1999). In addition to that, the quinazolinones exibit anti–bacterial and anti–bacterial and anti-fungal activities (Priya et al., 2011).

In title molecule (Fig. 1), the quinazoline unit is essentially planar, with a mean deviation of 0.027 (2) Å from the least–squares plane defined by the ten constituent atoms. The dihedral angle formed by the 4-chlorophenyl ring and the mean plane of the quinazoline fragment is 44.63 (5)°. In the crystal packing (Fig. 2), molecules are linked by intermolecular C—H···N and C—H···O hydrogen bonds (Table 1). These hydrogen bonds are forming infinite chains of alternating R₂²(6) dimer and R₂²(14) ring motifs (Bernstein et al., 1995) as shown in Fig. 2.

Experimental

To an ice–cold solution of POCl₃ in DMF was added anthranilic acid (0.01458 mole) and stirred for 5–10 min until TLC indicated the disappearance of anthranilic acid. The reaction-mixture was treated with the respective primary aromatic amine (0.01458 mol) and supported on anhydrous sodium sulfate (five times the weight of anthranilic acid) and exposed to microwave (BPL company) irradiation (600 W) for 2–4 min with 30 sec pulse. The reaction-mixture was quenched with water (50 ml) and extracted with ethyl acetate (2x50 ml). The organic layer was dried over anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (60–20 mesh) using hexane/EtOAc (7.5:2.5) as eluent to yield the pure product. Single crystals suitable for X–ray diffraction were prepared by slow evaporation of a solution of the title compound in methanol at room temperature.