2-(2-Chloro-phen-yl)-2,3-dihydro-quinazolin-4(1H)-one.

The title compound, C(14)H(11)ClN(2)O, was synthesized by the reaction of 2-chloro-benzaldehyde and 2-amino-benzamide in an ionic liquid. The pyrimidine ring adopts a skew-boat conformation and the two benzene rings make a dihedral angle of 87.1 (1)°. In the crystal, N-H⋯O and C-H⋯N hydrogen bonding links the mol-ecules along b.

Related literature

For quinazoline derivatives as anti­tumor agents, see: Feng et al. (2006 ▶); Keenan & Shakespear (2004 ▶); Mikiciuk-Olasik et al. (2004 ▶). For the biological activity of quinazoline derivatives, see: Bedi et al. (2004 ▶); Lin et al. (2006 ▶); Saleh et al. (2004 ▶).

Experimental

Crystal data

C14H11ClN2O

M = 258.70

Triclinic,

a = 6.9900 (1) Å

b = 8.7488 (2) Å

c = 10.4756 (2) Å

α = 100.639 (1)°

β = 92.726 (1)°

γ = 101.786 (1)°

V = 613.91 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.47 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (Jacobson, 1998 ▶) T min = 0.901, T max = 0.950

8018 measured reflections

2204 independent reflections

2029 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.082

S = 1.07

2204 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031328/pb2004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031328/pb2004Isup2.hkl

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

C14H11ClN2O	Z = 2
Mr = 258.70	F(000) = 268
Triclinic, P1	Dx = 1.399 Mg m−3
Hall symbol: -P 1	Melting point = 485–486 K
a = 6.9900 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.7488 (2) Å	Cell parameters from 5614 reflections
c = 10.4756 (2) Å	θ = 2.4–27.3°
α = 100.639 (1)°	µ = 0.30 mm−1
β = 92.726 (1)°	T = 296 K
γ = 101.786 (1)°	Block, colourless
V = 613.91 (2) Å3	0.47 × 0.15 × 0.15 mm

Bruker SMART CCD area-detector diffractometer	2204 independent reflections
Radiation source: fine-focus sealed tube	2029 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 25.2°, θmin = 2.0°
Absorption correction: multi-scan (Jacobson, 1998)	h = −8→8
Tmin = 0.901, Tmax = 0.950	k = −10→10
8018 measured reflections	l = −12→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0395P)2 + 0.1722P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2204 reflections	Δρmax = 0.20 e Å−3
176 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (4)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.16029 (5)	0.69778 (5)	0.05650 (4)	0.05390 (17)
N2	0.50252 (18)	1.00296 (13)	0.18929 (11)	0.0344 (3)
C9	0.53903 (19)	0.72253 (15)	0.14393 (12)	0.0301 (3)
O1	1.08313 (14)	1.09067 (13)	0.17031 (11)	0.0497 (3)
C2	0.9066 (2)	1.04662 (16)	0.18541 (14)	0.0370 (3)
C8	0.61534 (19)	1.08206 (15)	0.30290 (12)	0.0319 (3)
N1	0.78205 (17)	0.94682 (14)	0.09040 (12)	0.0367 (3)
C14	0.3498 (2)	0.62845 (16)	0.12560 (13)	0.0345 (3)
C1	0.57649 (19)	0.88323 (15)	0.10227 (13)	0.0315 (3)
C10	0.6833 (2)	0.66331 (18)	0.20113 (14)	0.0411 (3)
H10A	0.8115	0.7230	0.2153	0.049*
C13	0.3048 (2)	0.48197 (17)	0.16089 (15)	0.0451 (4)
H13A	0.1769	0.4217	0.1469	0.054*
C3	0.8198 (2)	1.10531 (17)	0.30508 (13)	0.0384 (3)
C7	0.5326 (2)	1.14921 (18)	0.41197 (14)	0.0419 (3)
H7A	0.3970	1.1339	0.4120	0.050*
C11	0.6398 (3)	0.5163 (2)	0.23777 (16)	0.0521 (4)
H11A	0.7385	0.4786	0.2765	0.063*
C4	0.9362 (2)	1.1958 (2)	0.41504 (17)	0.0613 (5)
H4A	1.0720	1.2122	0.4163	0.074*
C12	0.4514 (3)	0.42650 (18)	0.21692 (16)	0.0517 (4)
H12A	0.4232	0.3277	0.2409	0.062*
C6	0.6509 (3)	1.2379 (2)	0.51937 (16)	0.0582 (5)
H6A	0.5944	1.2828	0.5916	0.070*
C5	0.8526 (3)	1.2615 (3)	0.52208 (17)	0.0722 (6)
H5A	0.9312	1.3214	0.5957	0.087*
H2A	0.382 (2)	0.9860 (18)	0.1921 (14)	0.037 (4)*
H1A	0.823 (2)	0.9236 (19)	0.0184 (18)	0.045 (4)*
H1B	0.510 (2)	0.8682 (16)	0.0185 (14)	0.027 (3)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0326 (2)	0.0464 (2)	0.0788 (3)	0.00346 (16)	−0.01097 (18)	0.01200 (19)
N2	0.0259 (6)	0.0347 (6)	0.0423 (7)	0.0069 (5)	0.0038 (5)	0.0067 (5)
C9	0.0304 (7)	0.0324 (6)	0.0270 (6)	0.0067 (5)	0.0065 (5)	0.0041 (5)
O1	0.0298 (5)	0.0554 (7)	0.0566 (7)	−0.0007 (5)	0.0140 (5)	0.0007 (5)
C2	0.0310 (7)	0.0380 (7)	0.0418 (8)	0.0051 (6)	0.0087 (6)	0.0084 (6)
C8	0.0330 (7)	0.0308 (6)	0.0347 (7)	0.0076 (5)	0.0059 (5)	0.0119 (5)
N1	0.0338 (6)	0.0396 (6)	0.0339 (6)	0.0012 (5)	0.0126 (5)	0.0050 (5)
C14	0.0329 (7)	0.0334 (7)	0.0350 (7)	0.0055 (6)	0.0015 (5)	0.0034 (5)
C1	0.0292 (7)	0.0347 (7)	0.0298 (7)	0.0041 (5)	0.0032 (5)	0.0073 (5)
C10	0.0342 (8)	0.0447 (8)	0.0456 (8)	0.0101 (6)	0.0034 (6)	0.0105 (6)
C13	0.0473 (9)	0.0339 (7)	0.0481 (9)	−0.0027 (6)	0.0017 (7)	0.0063 (6)
C3	0.0327 (7)	0.0448 (8)	0.0368 (7)	0.0081 (6)	0.0049 (6)	0.0060 (6)
C7	0.0395 (8)	0.0473 (8)	0.0431 (8)	0.0148 (6)	0.0130 (6)	0.0118 (6)
C11	0.0576 (10)	0.0484 (9)	0.0569 (10)	0.0218 (8)	−0.0019 (8)	0.0175 (7)
C4	0.0382 (9)	0.0858 (13)	0.0502 (10)	0.0114 (9)	−0.0030 (7)	−0.0067 (9)
C12	0.0676 (11)	0.0326 (7)	0.0546 (9)	0.0063 (7)	0.0013 (8)	0.0139 (7)
C6	0.0641 (11)	0.0729 (12)	0.0372 (8)	0.0220 (9)	0.0126 (7)	0.0002 (8)
C5	0.0615 (12)	0.0989 (15)	0.0431 (10)	0.0171 (11)	−0.0070 (8)	−0.0161 (9)

Cl1—C14	1.7453 (14)	C10—C11	1.388 (2)
N2—C8	1.3787 (17)	C10—H10A	0.9300
N2—C1	1.4523 (17)	C13—C12	1.372 (2)
N2—H2A	0.831 (16)	C13—H13A	0.9300
C9—C10	1.3839 (19)	C3—C4	1.388 (2)
C9—C14	1.3915 (19)	C7—C6	1.371 (2)
C9—C1	1.5240 (18)	C7—H7A	0.9300
O1—C2	1.2421 (17)	C11—C12	1.373 (2)
C2—N1	1.3405 (18)	C11—H11A	0.9300
C2—C3	1.4716 (19)	C4—C5	1.375 (2)
C8—C7	1.3924 (19)	C4—H4A	0.9300
C8—C3	1.4001 (19)	C12—H12A	0.9300
N1—C1	1.4511 (17)	C6—C5	1.380 (3)
N1—H1A	0.824 (18)	C6—H6A	0.9300
C14—C13	1.378 (2)	C5—H5A	0.9300
C1—H1B	0.948 (14)
C8—N2—C1	118.48 (11)	C11—C10—H10A	119.5
C8—N2—H2A	116.8 (10)	C12—C13—C14	118.97 (14)
C1—N2—H2A	116.0 (10)	C12—C13—H13A	120.5
C10—C9—C14	116.97 (12)	C14—C13—H13A	120.5
C10—C9—C1	123.74 (12)	C4—C3—C8	119.58 (13)
C14—C9—C1	119.28 (11)	C4—C3—C2	121.32 (14)
O1—C2—N1	121.40 (13)	C8—C3—C2	118.80 (12)
O1—C2—C3	122.54 (13)	C6—C7—C8	120.05 (14)
N1—C2—C3	116.00 (12)	C6—C7—H7A	120.0
N2—C8—C7	121.83 (12)	C8—C7—H7A	120.0
N2—C8—C3	118.83 (12)	C12—C11—C10	120.13 (14)
C7—C8—C3	119.18 (13)	C12—C11—H11A	119.9
C2—N1—C1	124.90 (12)	C10—C11—H11A	119.9
C2—N1—H1A	117.9 (12)	C5—C4—C3	120.63 (16)
C1—N1—H1A	117.1 (12)	C5—C4—H4A	119.7
C13—C14—C9	122.57 (13)	C3—C4—H4A	119.7
C13—C14—Cl1	118.17 (11)	C13—C12—C11	120.28 (14)
C9—C14—Cl1	119.26 (10)	C13—C12—H12A	119.9
N1—C1—N2	108.17 (11)	C11—C12—H12A	119.9
N1—C1—C9	113.41 (11)	C7—C6—C5	121.06 (15)
N2—C1—C9	112.80 (10)	C7—C6—H6A	119.5
N1—C1—H1B	106.9 (8)	C5—C6—H6A	119.5
N2—C1—H1B	107.8 (8)	C4—C5—C6	119.49 (16)
C9—C1—H1B	107.5 (8)	C4—C5—H5A	120.3
C9—C10—C11	121.08 (14)	C6—C5—H5A	120.3
C9—C10—H10A	119.5
C1—N2—C8—C7	−154.80 (12)	Cl1—C14—C13—C12	−179.15 (12)
C1—N2—C8—C3	29.94 (17)	N2—C8—C3—C4	174.78 (14)
O1—C2—N1—C1	176.67 (13)	C7—C8—C3—C4	−0.6 (2)
C3—C2—N1—C1	−5.9 (2)	N2—C8—C3—C2	0.93 (19)
C10—C9—C14—C13	−0.6 (2)	C7—C8—C3—C2	−174.45 (13)
C1—C9—C14—C13	−179.95 (12)	O1—C2—C3—C4	−9.3 (2)
C10—C9—C14—Cl1	178.92 (10)	N1—C2—C3—C4	173.25 (15)
C1—C9—C14—Cl1	−0.48 (16)	O1—C2—C3—C8	164.39 (14)
C2—N1—C1—N2	33.01 (17)	N1—C2—C3—C8	−13.0 (2)
C2—N1—C1—C9	−92.90 (15)	N2—C8—C7—C6	−174.73 (14)
C8—N2—C1—N1	−44.49 (15)	C3—C8—C7—C6	0.5 (2)
C8—N2—C1—C9	81.78 (14)	C9—C10—C11—C12	0.3 (2)
C10—C9—C1—N1	17.84 (18)	C8—C3—C4—C5	0.6 (3)
C14—C9—C1—N1	−162.81 (11)	C2—C3—C4—C5	174.27 (18)
C10—C9—C1—N2	−105.57 (14)	C14—C13—C12—C11	0.3 (2)
C14—C9—C1—N2	73.78 (15)	C10—C11—C12—C13	−0.6 (3)
C14—C9—C10—C11	0.2 (2)	C8—C7—C6—C5	−0.4 (3)
C1—C9—C10—C11	179.58 (13)	C3—C4—C5—C6	−0.5 (3)
C9—C14—C13—C12	0.3 (2)	C7—C6—C5—C4	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.831 (16)	2.461 (16)	3.1847 (16)	146.2 (14)
N1—H1A···O1ii	0.824 (18)	2.103 (18)	2.9146 (16)	168.4 (16)
C1—H1B···N2iii	0.948 (14)	2.635 (14)	3.4369 (17)	142.6 (11)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.831 (16)	2.461 (16)	3.1847 (16)	146.2 (14)
N1—H1A⋯O1ii	0.824 (18)	2.103 (18)	2.9146 (16)	168.4 (16)
C1—H1B⋯N2iii	0.948 (14)	2.635 (14)	3.4369 (17)	142.6 (11)

Symmetry codes: (i) ; (ii) ; (iii) .