3-(4-Bromo-phen-yl)quinazolin-4(3H)-one.

In the title compound, C(14)H(9)BrN(2)O, 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-bromo-phenyl ring is 47.6 (1)°. In the crystal, mol-ecules are linked by inter-molecular 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 = 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

Δρmax = 0.34 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811040736/im2320sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811040736/im2320Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H9BrN2O	F(000) = 600
Mr = 301.14	Dx = 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

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

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(Fo2) + (0.0381P)2 + 0.2934P] where P = (Fo2 + 2Fc2)/3
2840 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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.

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) ; (ii) .