2-(5-Bromo-2-hydroxy­phen­yl)-1,2-dihydro­quinazolin-4(3H)-one

Davar M Boghaei; Mohammad Mahdi Najafpour; Vickie McKee

doi:10.1107/S1600536808035678

. 2008 Dec 24;65(Pt 1):o193. doi: 10.1107/S1600536808035678

2-(5-Bromo-2-hydroxyphenyl)-1,2-dihydroquinazolin-4(3H)-one

Davar M Boghaei ^a,^*, Mohammad Mahdi Najafpour ^a, Vickie McKee ^b

PMCID: PMC2968101 PMID: 21581648

Abstract

The asymmetric unit of the title compound, C₁₄H₁₁BrN₂O₂, contains two independent molecules connected into a dimer by intermolecular N—H⋯O hydrogen bonds involving the amine and carbonyl groups. The dimers are further connected by O—H⋯O hydrogen bonds, forming chains running parallel to the a axis, which are stabilized through π–π stacking interactions, with a centroid–centroid distance of 3.679 (8) Å. The dihedral angle between the two aromatic rings is 89.2 (4)°.

Related literature

For general background to the chemistry of quinazolinone derivatives, see: Liu (2008 ▶); Goto et al. (1993 ▶); Mohri (2001 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₁BrN₂O₂
M _r = 319.16
Triclinic,
a = 8.8392 (5) Å
b = 11.2252 (7) Å
c = 13.8817 (8) Å
α = 73.0392 (9)°
β = 75.9620 (9)°
γ = 85.0936 (9)°
V = 1277.95 (13) Å³
Z = 4
Mo Kα radiation
μ = 3.21 mm⁻¹
T = 150 (2) K
0.21 × 0.12 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.552, T _max = 0.806
13015 measured reflections
6129 independent reflections
4580 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.099
S = 1.02
6129 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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, New_Global_Publ_Block. DOI: 10.1107/S1600536808035678/rz2254sup1.cif

e-65-0o193-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035678/rz2254Isup2.hkl

e-65-0o193-Isup2.hkl^{(300KB, 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
N2A—H2NA⋯O1B	0.95	1.97	2.897 (3)	165
N2B—H2NB⋯O1A	0.91	2.05	2.914 (3)	157
O2A—H2OA⋯O1Aⁱ	0.85	1.90	2.701 (3)	157
O2B—H2OB⋯O1Bⁱⁱ	0.85	1.86	2.691 (3)	165

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

Acknowledgments

We are grateful to the Research Council of Sharif University of Technology and Loughborough University for their financial support.

supplementary crystallographic information

Comment

Quinazolinone derivatives are of interest because of their biological activity, and have been widely used as key compounds in medicinal drugs (Goto et al., 1993; Mohri, 2001). We herein report the crystal structure of 1,2-dihydro-2-(5-bromo-2-hydroxybenzene)-4(3H)-quinazolinone.

The asymmentric unit of the title compound (Fig. 1) contains two crystallographically independent molecules, which are linked into a dimer by a pair of intermolecular N—H···O hydrogen bonds (Table 1), generating a ring of graph set R²₂(8) (Bernstein et al., 1995). Bond lengths and angles are within normal ranges. The dimers are further connected by O—H···O hydrogen bonding interactions to form chains running parallel to the a axis (Figures 2). The chains are stabilized by π–π stacking interactions involving adjacent 5-bromo-2-hydroxybenzene rings, with a centroid-centroid separation of 3.679 (8) Å, a perpendicular interplanar distance of 3.561 (8) Å and a centroid···centroid offset of 0.924 (6) Å.

Experimental

The title compound was synthesized by adding 5-bromo-2-hydroxybenzaldehyde (2 mmol, 402 mg) to a solution of 2-aminobenzamide (2 mmol, 272 mg) and manganese acetate (0.02 mmol, 4.90 mg) in ethanol (20 ml). The mixture was refluxed with stirring for 5 h. The resultant yellow solution was filtered. Yellow single crystals of the title compound suitable for X-ray structure determination were recrystallized from a mixture of water/ethanol (2:1 v/v) by slow evaporation of the solvents at room temperature over several days.