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

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

doi:10.1107/S1600536811040736

. 2011 Oct 12;67(Pt 11):o2928. doi: 10.1107/S1600536811040736

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

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

PMCID: PMC3247341 PMID: 22219959

Abstract

In the title compound, C₁₄H₉BrN₂O, the quinazoline unit is essentially planar, with a mean deviation of 0.058 (2) Å from the least-squares plane defined by the ten constituent ring atoms. The dihedral angle between the mean plane of the quinazoline ring system and the 4-bromophenyl ring is 47.6 (1)°. In the crystal, molecules are linked by intermolecular C—H⋯N and C—H⋯O hydrogen bonds, forming infinite chains of alternating R ₂ ²(6) dimers and R ₂ ²(14) ring motifs.

Related literature

For the synthesis of the title compound, see: Priya, Zulykama et al. (2011 ▶). For a related structure, see: Priya, Srinivasan et al. (2011 ▶). 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

C₁₄H₉BrN₂O
M _r = 301.14
Monoclinic,
a = 16.961 (3) Å
b = 3.9530 (8) Å
c = 17.698 (3) Å
β = 93.168 (11)°
V = 1184.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 3.46 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
10371 measured reflections
2840 independent reflections
1772 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.094
S = 1.01
2840 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.54 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/S1600536811040736/im2320sup1.cif

e-67-o2928-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040736/im2320Isup2.hkl

e-67-o2928-Isup2.hkl^{(136.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811040736/im2320Isup3.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
C8—H8⋯N1ⁱ	0.93	2.48	3.286 (4)	146
C11—H11⋯O1ⁱⁱ	0.93	2.32	3.224 (4)	165

Open in a new tab

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 TS also thanks the DST for the Inspire fellowship

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) and anti-HIV (Pandeya et al., 1999). In addition to that, quinazolinones exibit anti-bacterial and anti-fungal activities (Priya, Zulykama et al., 2011).

In title molecule (Fig. 1), the quinazoline unit is essentially planar, with a mean deviation of 0.058 (2) Å from the least square plane defined by the ten constituent atoms. The dihedral angle formed by the 4-bromophenyl ring and the mean plane of the quinazoline fragment is 47.6 (1)° . In the crystal packing, 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 2.8 ml POCl₃ in 5 ml DMF was added anthranilic acid (2 g, 0.0146 mole) and stirred for 5-10 min until TLC indicated the disappearance of anthranilic acid. The reaction mixture was then treated with an equimolar amount of p-bromo-aniline (2.511 g) 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 (2 x 50 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 (yield: 4,397 g, 84%). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in methanol at room temperature.