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

In the title compound, C(14)H(9)ClN(2)O, 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-chloro-phenyl ring is 44.63 (5)°. 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 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 = 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

Δρmax = 0.27 e Å−3

Δρmin = −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 ▶).

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

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

Supplementary material file. DOI: 10.1107/S1600536811030935/lx2195Isup3.cml

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

C14H9ClN2O	F(000) = 528
Mr = 256.68	Dx = 1.482 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1025 reflections
a = 16.9531 (8) Å	θ = 1.7–28.5°
b = 3.9290 (3) Å	µ = 0.32 mm−1
c = 17.2740 (8) Å	T = 293 K
β = 91.626 (3)°	Block, colourless
V = 1150.14 (12) Å3	0.24 × 0.22 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	2920 independent reflections
Radiation source: fine-focus sealed tube	1870 reflections with I > 2σ(I)
graphite	Rint = 0.042
ω and φ scans	θmax = 28.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −22→21
Tmin = 0.926, Tmax = 0.938	k = −5→5
11055 measured 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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F2) = 0.133	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0705P)2 + 0.0848P] where P = (Fo2 + 2Fc2)/3
2920 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.22 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
Cl1	0.91232 (3)	0.26102 (17)	0.49055 (3)	0.0650 (2)
O1	0.61097 (8)	0.3729 (5)	0.25686 (8)	0.0644 (5)
C1	0.46221 (11)	0.6243 (6)	0.19774 (10)	0.0517 (5)
H1	0.4933	0.5149	0.1619	0.062*
C2	0.38879 (13)	0.7399 (6)	0.17572 (11)	0.0578 (5)
H2	0.3704	0.7118	0.1249	0.069*
C3	0.34179 (12)	0.8996 (6)	0.22962 (12)	0.0575 (5)
H3	0.2916	0.9752	0.2148	0.069*
C4	0.36884 (11)	0.9464 (6)	0.30462 (11)	0.0525 (5)
H4	0.3370	1.0538	0.3402	0.063*
C5	0.44358 (10)	0.8339 (5)	0.32744 (9)	0.0419 (4)
C6	0.49087 (10)	0.6695 (5)	0.27370 (9)	0.0426 (4)
C7	0.54095 (11)	0.7942 (5)	0.42122 (9)	0.0445 (4)
H7	0.5590	0.8353	0.4717	0.053*
C8	0.56863 (10)	0.5452 (5)	0.29697 (9)	0.0448 (4)
C9	0.67020 (10)	0.5459 (5)	0.40206 (8)	0.0405 (4)
C10	0.68006 (10)	0.3971 (5)	0.47428 (9)	0.0455 (4)
H10	0.6363	0.3521	0.5039	0.055*
C11	0.75439 (11)	0.3154 (5)	0.50233 (10)	0.0486 (5)
H11	0.7613	0.2197	0.5513	0.058*
C12	0.81859 (10)	0.3767 (5)	0.45721 (10)	0.0452 (4)
C13	0.80960 (10)	0.5292 (6)	0.38568 (9)	0.0480 (5)
H13	0.8535	0.5725	0.3562	0.058*
C14	0.73563 (10)	0.6173 (5)	0.35806 (9)	0.0452 (4)
H14	0.7293	0.7240	0.3102	0.054*
N1	0.47068 (8)	0.8923 (5)	0.40344 (8)	0.0477 (4)
N2	0.59244 (8)	0.6340 (4)	0.37290 (7)	0.0407 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0495 (3)	0.0838 (5)	0.0615 (3)	0.0035 (3)	−0.0001 (2)	0.0062 (3)
O1	0.0570 (8)	0.0892 (13)	0.0473 (7)	0.0129 (8)	0.0066 (6)	−0.0291 (7)
C1	0.0586 (11)	0.0583 (14)	0.0383 (9)	−0.0053 (10)	0.0062 (8)	−0.0070 (8)
C2	0.0656 (12)	0.0634 (15)	0.0440 (10)	−0.0081 (10)	−0.0057 (9)	0.0006 (9)
C3	0.0517 (11)	0.0605 (15)	0.0602 (11)	−0.0006 (10)	−0.0027 (9)	0.0063 (10)
C4	0.0504 (10)	0.0526 (14)	0.0550 (10)	−0.0007 (9)	0.0110 (8)	−0.0012 (9)
C5	0.0440 (9)	0.0444 (12)	0.0377 (8)	−0.0070 (7)	0.0090 (7)	−0.0022 (7)
C6	0.0484 (9)	0.0436 (12)	0.0362 (8)	−0.0077 (8)	0.0083 (7)	−0.0036 (7)
C7	0.0466 (9)	0.0546 (13)	0.0329 (8)	−0.0053 (8)	0.0117 (7)	−0.0093 (7)
C8	0.0485 (10)	0.0515 (13)	0.0349 (8)	−0.0036 (8)	0.0095 (7)	−0.0097 (8)
C9	0.0447 (9)	0.0437 (12)	0.0334 (8)	−0.0052 (8)	0.0085 (6)	−0.0051 (7)
C10	0.0477 (10)	0.0545 (13)	0.0349 (8)	−0.0097 (8)	0.0131 (7)	0.0009 (8)
C11	0.0542 (11)	0.0560 (14)	0.0359 (8)	−0.0071 (9)	0.0062 (7)	0.0047 (8)
C12	0.0441 (9)	0.0493 (12)	0.0424 (9)	−0.0026 (8)	0.0050 (7)	−0.0003 (8)
C13	0.0453 (10)	0.0566 (14)	0.0428 (9)	−0.0072 (9)	0.0138 (7)	0.0022 (8)
C14	0.0513 (10)	0.0506 (12)	0.0343 (8)	−0.0054 (8)	0.0109 (7)	0.0021 (8)
N1	0.0475 (8)	0.0582 (11)	0.0378 (7)	0.0000 (7)	0.0116 (6)	−0.0109 (7)
N2	0.0419 (7)	0.0492 (10)	0.0315 (6)	−0.0021 (6)	0.0088 (5)	−0.0074 (6)

Cl1—C12	1.7353 (18)	C7—N2	1.377 (2)
O1—C8	1.217 (2)	C7—H7	0.9300
C1—C2	1.369 (3)	C8—N2	1.405 (2)
C1—C6	1.397 (2)	C9—C10	1.384 (2)
C1—H1	0.9300	C9—C14	1.391 (2)
C2—C3	1.392 (3)	C9—N2	1.440 (2)
C2—H2	0.9300	C10—C11	1.375 (3)
C3—C4	1.374 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.378 (2)
C4—C5	1.389 (3)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.378 (3)
C5—N1	1.398 (2)	C13—C14	1.373 (3)
C5—C6	1.401 (2)	C13—H13	0.9300
C6—C8	1.452 (3)	C14—H14	0.9300
C7—N1	1.281 (2)
C2—C1—C6	120.52 (18)	N2—C8—C6	114.17 (14)
C2—C1—H1	119.7	C10—C9—C14	120.00 (16)
C6—C1—H1	119.7	C10—C9—N2	120.19 (14)
C1—C2—C3	119.81 (18)	C14—C9—N2	119.79 (15)
C1—C2—H2	120.1	C11—C10—C9	120.16 (15)
C3—C2—H2	120.1	C11—C10—H10	119.9
C4—C3—C2	120.59 (19)	C9—C10—H10	119.9
C4—C3—H3	119.7	C10—C11—C12	119.38 (16)
C2—C3—H3	119.7	C10—C11—H11	120.3
C3—C4—C5	120.15 (18)	C12—C11—H11	120.3
C3—C4—H4	119.9	C13—C12—C11	120.94 (16)
C5—C4—H4	119.9	C13—C12—Cl1	119.24 (13)
C4—C5—N1	119.17 (16)	C11—C12—Cl1	119.81 (14)
C4—C5—C6	119.56 (16)	C14—C13—C12	119.86 (16)
N1—C5—C6	121.26 (16)	C14—C13—H13	120.1
C1—C6—C5	119.36 (17)	C12—C13—H13	120.1
C1—C6—C8	120.40 (16)	C13—C14—C9	119.60 (16)
C5—C6—C8	120.24 (15)	C13—C14—H14	120.2
N1—C7—N2	126.39 (15)	C9—C14—H14	120.2
N1—C7—H7	116.8	C7—N1—C5	117.04 (14)
N2—C7—H7	116.8	C7—N2—C8	120.60 (14)
O1—C8—N2	120.72 (16)	C7—N2—C9	119.18 (13)
O1—C8—C6	125.10 (15)	C8—N2—C9	120.18 (13)
C6—C1—C2—C3	−0.9 (3)	C10—C11—C12—Cl1	−177.74 (16)
C1—C2—C3—C4	0.9 (3)	C11—C12—C13—C14	−1.0 (3)
C2—C3—C4—C5	−0.1 (3)	Cl1—C12—C13—C14	178.99 (16)
C3—C4—C5—N1	178.32 (19)	C12—C13—C14—C9	−1.1 (3)
C3—C4—C5—C6	−0.6 (3)	C10—C9—C14—C13	2.1 (3)
C2—C1—C6—C5	0.2 (3)	N2—C9—C14—C13	−179.22 (18)
C2—C1—C6—C8	179.71 (19)	N2—C7—N1—C5	−0.6 (3)
C4—C5—C6—C1	0.6 (3)	C4—C5—N1—C7	−177.73 (19)
N1—C5—C6—C1	−178.32 (18)	C6—C5—N1—C7	1.2 (3)
C4—C5—C6—C8	−178.96 (18)	N1—C7—N2—C8	−3.5 (3)
N1—C5—C6—C8	2.1 (3)	N1—C7—N2—C9	178.92 (19)
C1—C6—C8—O1	−6.6 (3)	O1—C8—N2—C7	−172.35 (19)
C5—C6—C8—O1	172.9 (2)	C6—C8—N2—C7	6.3 (3)
C1—C6—C8—N2	174.76 (17)	O1—C8—N2—C9	5.2 (3)
C5—C6—C8—N2	−5.7 (3)	C6—C8—N2—C9	−176.13 (16)
C14—C9—C10—C11	−0.8 (3)	C10—C9—N2—C7	44.8 (3)
N2—C9—C10—C11	−179.52 (18)	C14—C9—N2—C7	−133.95 (19)
C9—C10—C11—C12	−1.4 (3)	C10—C9—N2—C8	−132.82 (19)
C10—C11—C12—C13	2.3 (3)	C14—C9—N2—C8	48.5 (3)

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

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

Symmetry codes: (i) ; (ii) .