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

Srinivasan, T.; Suhitha, S.; Priya, M.G.R.; Girija, K.; Chandran, N.R.; Velmurugan, D.

doi:10.1107/S1600536811040736

organic compounds

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Volume 67| Part 11| November 2011| Page o2928

doi:10.1107/S1600536811040736

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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 and D. Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, ^bDepartment of Chemistry, Sastra University, Thanjavur 613 402, India, ^cMother Theresa Postgraduate & Health Science, Puducherry 605 006, India, and ^dDepartment of Carism, Sastra University, Thanjavur 613 402, India
^*Correspondence e-mail: shirai2011@gmail.com

(Received 15 September 2011; accepted 3 October 2011; online 12 October 2011)

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 R₂²(6) dimers and R₂²(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, P 2₁ /n
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[F² > 2σ(F²)] = 0.036
wR(F²) = 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

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
Symmetry codes: (i) -x+1, -y-1, -z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811040736/im2320sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811040736/im2320Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. View of the C–H···N and C–H···O hydrogen bonds (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 1, - y -1, - z; (ii) - x +1/2, y - 1/2, - z + 1/2.]

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

Crystal data top

C₁₄H₉BrN₂O	F(000) = 600
M_r = 301.14	D_x = 1.688 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2840 reflections
a = 16.961 (3) Å	θ = 1.6–28.3°
b = 3.9530 (8) Å	µ = 3.46 mm⁻¹
c = 17.698 (3) Å	T = 293 K
β = 93.168 (11)°	Block, colourless
V = 1184.8 (4) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	1772 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.050
Graphite monochromator	θ_max = 28.3°, θ_min = 1.6°
ω and ϕ scans	h = −22→14
10371 measured reflections	k = −4→5
2840 independent reflections	l = −23→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0381P)² + 0.2934P] where P = (F_o² + 2F_c²)/3
2840 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₁₄H₉BrN₂O	V = 1184.8 (4) Å³
M_r = 301.14	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 16.961 (3) Å	µ = 3.46 mm⁻¹
b = 3.9530 (8) Å	T = 293 K
c = 17.698 (3) Å	0.20 × 0.20 × 0.20 mm
β = 93.168 (11)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.01	Δρ_max = 0.34 e Å⁻³
2840 reflections	Δρ_min = −0.54 e Å⁻³
163 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.30495 (19)	−0.4078 (7)	−0.13542 (16)	0.0457 (8)
H1	0.3413	−0.5172	−0.1644	0.055*
C2	0.22902 (19)	−0.3495 (8)	−0.16454 (17)	0.0494 (8)
H2	0.2143	−0.4201	−0.2134	0.059*
C3	0.17450 (19)	−0.1869 (8)	−0.12177 (18)	0.0500 (8)
H3	0.1233	−0.1520	−0.1418	0.060*
C4	0.19570 (17)	−0.0771 (8)	−0.04997 (17)	0.0445 (7)
H4	0.1591	0.0340	−0.0216	0.053*
C5	0.27242 (16)	−0.1327 (7)	−0.01962 (15)	0.0354 (7)
C6	0.32663 (17)	−0.3015 (7)	−0.06239 (15)	0.0360 (6)
N2	0.37065 (13)	−0.1237 (5)	0.08283 (12)	0.0338 (5)
C9	0.39734 (16)	−0.0577 (7)	0.15992 (14)	0.0340 (6)
C10	0.35023 (17)	−0.1470 (7)	0.21832 (16)	0.0424 (7)
H10	0.3018	−0.2522	0.2077	0.051*
C11	0.37520 (18)	−0.0797 (7)	0.29172 (16)	0.0430 (7)
H11	0.3434	−0.1357	0.3310	0.052*
C12	0.44731 (17)	0.0707 (7)	0.30707 (15)	0.0383 (7)
C13	0.49575 (17)	0.1529 (7)	0.24960 (16)	0.0440 (7)
H13	0.5449	0.2506	0.2607	0.053*
C14	0.47056 (16)	0.0889 (7)	0.17584 (16)	0.0397 (7)
H14	0.5026	0.1440	0.1367	0.048*
C7	0.29483 (16)	−0.0184 (8)	0.05649 (15)	0.0392 (7)
C8	0.41999 (17)	−0.2860 (7)	0.03558 (16)	0.0380 (7)
H8	0.4704	−0.3381	0.0556	0.046*
O1	0.25479 (13)	0.1572 (6)	0.09574 (12)	0.0599 (6)
N1	0.40348 (14)	−0.3727 (6)	−0.03334 (13)	0.0411 (6)
Br1	0.47919 (2)	0.17499 (9)	0.408526 (17)	0.05840 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.056 (2)	0.0462 (19)	0.0358 (15)	0.0011 (15)	0.0107 (14)	−0.0001 (13)
C2	0.057 (2)	0.053 (2)	0.0376 (15)	−0.0083 (17)	−0.0049 (15)	0.0042 (14)
C3	0.0436 (18)	0.056 (2)	0.0494 (18)	−0.0026 (16)	−0.0041 (15)	0.0095 (16)
C4	0.0351 (17)	0.0494 (19)	0.0493 (17)	0.0077 (14)	0.0058 (14)	0.0051 (14)
C5	0.0356 (16)	0.0347 (17)	0.0368 (14)	0.0037 (13)	0.0094 (12)	0.0068 (12)
C6	0.0361 (16)	0.0359 (15)	0.0367 (14)	0.0006 (13)	0.0081 (12)	0.0063 (12)
N2	0.0301 (12)	0.0408 (14)	0.0314 (11)	0.0064 (11)	0.0090 (9)	0.0002 (10)
C9	0.0335 (16)	0.0367 (16)	0.0325 (13)	0.0026 (13)	0.0077 (12)	0.0035 (12)
C10	0.0390 (17)	0.0477 (19)	0.0416 (15)	−0.0047 (14)	0.0122 (13)	0.0043 (14)
C11	0.0467 (18)	0.0506 (19)	0.0331 (14)	−0.0002 (15)	0.0153 (13)	0.0068 (13)
C12	0.0453 (18)	0.0410 (16)	0.0291 (13)	0.0023 (14)	0.0050 (12)	0.0026 (12)
C13	0.0379 (16)	0.0505 (19)	0.0434 (16)	−0.0070 (15)	0.0018 (13)	0.0042 (14)
C14	0.0341 (16)	0.0474 (19)	0.0389 (15)	−0.0011 (14)	0.0131 (12)	0.0086 (13)
C7	0.0316 (16)	0.0478 (18)	0.0390 (15)	0.0039 (15)	0.0083 (12)	0.0052 (14)
C8	0.0304 (15)	0.0447 (17)	0.0397 (15)	0.0077 (13)	0.0096 (12)	0.0039 (13)
O1	0.0482 (13)	0.0870 (17)	0.0452 (12)	0.0302 (12)	0.0080 (10)	−0.0133 (12)
N1	0.0372 (14)	0.0494 (16)	0.0377 (13)	0.0062 (12)	0.0117 (11)	−0.0007 (11)
Br1	0.0734 (3)	0.0652 (3)	0.03636 (18)	−0.00188 (19)	0.00039 (15)	−0.00357 (15)

Geometric parameters (Å, º) top

C1—C2	1.380 (4)	C9—C14	1.385 (4)
C1—C6	1.389 (4)	C9—C10	1.387 (4)
C1—H1	0.9300	C10—C11	1.370 (4)
C2—C3	1.385 (4)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.373 (4)
C3—C4	1.372 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.381 (4)
C4—C5	1.398 (4)	C12—Br1	1.892 (3)
C4—H4	0.9300	C13—C14	1.374 (4)
C5—C6	1.393 (4)	C13—H13	0.9300
C5—C7	1.451 (4)	C14—H14	0.9300
C6—N1	1.403 (4)	C7—O1	1.216 (3)
N2—C8	1.374 (3)	C8—N1	1.283 (4)
N2—C7	1.406 (3)	C8—H8	0.9300
N2—C9	1.437 (3)

C2—C1—C6	119.4 (3)	C10—C9—N2	119.8 (2)
C2—C1—H1	120.3	C11—C10—C9	119.8 (3)
C6—C1—H1	120.3	C11—C10—H10	120.1
C1—C2—C3	120.7 (3)	C9—C10—H10	120.1
C1—C2—H2	119.6	C10—C11—C12	119.8 (3)
C3—C2—H2	119.6	C10—C11—H11	120.1
C4—C3—C2	120.3 (3)	C12—C11—H11	120.1
C4—C3—H3	119.9	C11—C12—C13	121.0 (3)
C2—C3—H3	119.9	C11—C12—Br1	119.1 (2)
C3—C4—C5	119.8 (3)	C13—C12—Br1	119.8 (2)
C3—C4—H4	120.1	C14—C13—C12	119.3 (3)
C5—C4—H4	120.1	C14—C13—H13	120.3
C6—C5—C4	119.7 (3)	C12—C13—H13	120.3
C6—C5—C7	120.4 (2)	C13—C14—C9	119.9 (2)
C4—C5—C7	119.9 (2)	C13—C14—H14	120.1
C1—C6—C5	120.1 (3)	C9—C14—H14	120.1
C1—C6—N1	118.2 (3)	O1—C7—N2	120.6 (3)
C5—C6—N1	121.6 (2)	O1—C7—C5	125.6 (3)
C8—N2—C7	120.9 (2)	N2—C7—C5	113.8 (2)
C8—N2—C9	119.5 (2)	N1—C8—N2	126.5 (3)
C7—N2—C9	119.7 (2)	N1—C8—H8	116.7
C14—C9—C10	120.1 (3)	N2—C8—H8	116.7
C14—C9—N2	120.1 (2)	C8—N1—C6	116.4 (2)

C6—C1—C2—C3	0.0 (4)	C10—C11—C12—Br1	177.9 (2)
C1—C2—C3—C4	0.9 (5)	C11—C12—C13—C14	1.3 (5)
C2—C3—C4—C5	−0.6 (5)	Br1—C12—C13—C14	−177.3 (2)
C3—C4—C5—C6	−0.5 (4)	C12—C13—C14—C9	−0.2 (4)
C3—C4—C5—C7	−179.7 (3)	C10—C9—C14—C13	−1.5 (4)
C2—C1—C6—C5	−1.1 (4)	N2—C9—C14—C13	179.7 (3)
C2—C1—C6—N1	178.2 (2)	C8—N2—C7—O1	−171.8 (3)
C4—C5—C6—C1	1.3 (4)	C9—N2—C7—O1	7.5 (4)
C7—C5—C6—C1	−179.5 (3)	C8—N2—C7—C5	6.9 (4)
C4—C5—C6—N1	−177.9 (2)	C9—N2—C7—C5	−173.8 (2)
C7—C5—C6—N1	1.3 (4)	C6—C5—C7—O1	172.8 (3)
C8—N2—C9—C14	48.8 (4)	C4—C5—C7—O1	−8.0 (4)
C7—N2—C9—C14	−130.5 (3)	C6—C5—C7—N2	−5.9 (4)
C8—N2—C9—C10	−130.0 (3)	C4—C5—C7—N2	173.3 (2)
C7—N2—C9—C10	50.7 (4)	C7—N2—C8—N1	−3.4 (4)
C14—C9—C10—C11	2.1 (4)	C9—N2—C8—N1	177.3 (3)
N2—C9—C10—C11	−179.1 (3)	N2—C8—N1—C6	−1.7 (4)
C9—C10—C11—C12	−1.1 (5)	C1—C6—N1—C8	−176.6 (3)
C10—C11—C12—C13	−0.6 (5)	C5—C6—N1—C8	2.7 (4)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1, −y−1, −z; (ii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₉BrN₂O
M_r	301.14
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	16.961 (3), 3.9530 (8), 17.698 (3)
β (°)	93.168 (11)
V (Å³)	1184.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.46
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10371, 2840, 1772
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.094, 1.01
No. of reflections	2840
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.54

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N1ⁱ	0.93	2.48	3.286 (4)	145.7
C11—H11···O1ⁱⁱ	0.93	2.32	3.224 (4)	165.3

Symmetry codes: (i) −x+1, −y−1, −z; (ii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

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

References

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