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

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

doi:10.1107/S1600536811030935

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2310

doi:10.1107/S1600536811030935

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

M. Gnana Ruba Priya,^a T. Srinivasan,^b K. Girija,^c N. Ravi Chandran ^d and D. Velmurugan ^b ^*

^aDepartment of Chemistry, CNK Reddy College of Pharmacy, Sastra University, Thanjavur 613 402, India, ^bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, ^cMother Theresa Postgraduate & Health Science, Puducherry 605 006, India, and ^dSastra University, Thanjavur 613 402, India
^*Correspondence e-mail: dvelmurugan@unom.co.in

(Received 18 July 2011; accepted 1 August 2011; online 11 August 2011)

In the title compound, C₁₄H₉ClN₂O, 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-chlorophenyl ring is 44.63 (5)°. 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 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_r = 256.68
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.133
S = 1.01
2920 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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) -x+1, -y+2, -z+1; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536811030935/lx2195sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811030935/lx2195Isup3.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), anti–HIV (Pandeya et al., 1999). In addition to that, the quinazolinones exibit anti–bacterial and anti–bacterial and anti-fungal activities (Priya et al., 2011).

In title molecule (Fig. 1), the quinazoline unit is essentially planar, with a mean deviation of 0.027 (2) Å from the least–squares plane defined by the ten constituent atoms. The dihedral angle formed by the 4-chlorophenyl ring and the mean plane of the quinazoline fragment is 44.63 (5)°. In the crystal packing (Fig. 2), 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 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 top

To an ice–cold solution of POCl₃ in DMF was added anthranilic acid (0.01458 mole) and stirred for 5–10 min until TLC indicated the disappearance of anthranilic acid. The reaction-mixture was treated with the respective primary aromatic amine (0.01458 mol) 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 (2x50 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. 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. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. A 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 + 2, - z + 1; (ii) - x - 3/2, y + 1/2, - z + 1/2; (iii) - x + 3/2, y - 1/2, - z + 1/2.]

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

Crystal data top

C₁₄H₉ClN₂O	F(000) = 528
M_r = 256.68	D_x = 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

Data collection top

Bruker SMART APEXII area-detector diffractometer	2920 independent reflections
Radiation source: fine-focus sealed tube	1870 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω and ϕ scans	θ_max = 28.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −22→21
T_min = 0.926, T_max = 0.938	k = −5→5
11055 measured 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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F²) = 0.133	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0705P)² + 0.0848P] where P = (F_o² + 2F_c²)/3
2920 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₄H₉ClN₂O	V = 1150.14 (12) Å³
M_r = 256.68	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 16.9531 (8) Å	µ = 0.32 mm⁻¹
b = 3.9290 (3) Å	T = 293 K
c = 17.2740 (8) Å	0.24 × 0.22 × 0.20 mm
β = 91.626 (3)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	2920 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1870 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.938	R_int = 0.042
11055 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.01	Δρ_max = 0.27 e Å⁻³
2920 reflections	Δρ_min = −0.22 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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+1; (ii) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₉ClN₂O
M_r	256.68
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	16.9531 (8), 3.9290 (3), 17.2740 (8)
β (°)	91.626 (3)
V (Å³)	1150.14 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.24 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.926, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	11055, 2920, 1870
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.133, 1.01
No. of reflections	2920
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.22

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
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) −x+1, −y+2, −z+1; (ii) −x+3/2, 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 a DST inspire fellowship for financial support

References

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