2-Chloro­quinazolin-4(3H)-one

Abstract

In the title compound, C₈H₅ClN₂O, the quinazoline system is approximately planar with a maximum deviation from the least-squares plane of 0.034 (2) Å. In the crystal, classical N—H⋯O and weak non-classical C—H⋯N hydrogen bonds link the mol­ecules.

Related literature  

For the synthesis, see: Feng et al. (2007 ▶). For applications of related compounds, see: Labuda et al. (2009 ▶).

Experimental  

Crystal data  

• C₈H₅ClN₂O

• M _r = 180.59

• Monoclinic,

• a = 22.4315 (16) Å

• b = 3.7666 (6) Å

• c = 18.0640 (13) Å

• β = 104.682 (7)°

• V = 1476.4 (3) ų

• Z = 8

• Mo Kα radiation

• μ = 0.46 mm⁻¹

• T = 113 K

• 0.20 × 0.18 × 0.14 mm

Data collection  

• Rigaku Saturn CCD diffractometer

• Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.914, T _max = 0.939

• 6933 measured reflections

• 1749 independent reflections

• 1430 reflections with I > 2σ(I)

• R _int = 0.038

Refinement  

• R[F ² > 2σ(F ²)] = 0.036

• wR(F ²) = 0.095

• S = 1.03

• 1749 reflections

• 113 parameters

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.45 e Å⁻³

• Δρ_min = −0.23 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2006 ▶).

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536812022891/rk2353Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O1i	0.92 (2)	1.88 (2)	2.7840 (17)	166.5 (19)
C3—H3⋯N1ii	0.95	2.53	3.449 (2)	163

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

Comment

Quinazolin-4(3H)-ones and related quinazolines are classes of fused heterocycles that are of consider able interest because of the diverse range of their biological properties, for example, anticancer, anti-inflammatory, diuretic, anticonvulsant and antihypertensive activities (Labuda et al., 2009). The title compound (Fig. 1) consists of a quinazoline ring with an Cl atom at C4. The quinazoline heterobicycle is nearly planar, with a maximum deviation from the least-squares plane of 0.034 (2)Å. All bond lengths and angles are normal, atoms O1 and Cl lie in the 2-chloroquinazolin ring (C1-C8/N1/N2) plane. In addition, two intermolecular hydrogen bonding (classical N–H···O and non-classical C–H···N) (Table 1, Fig. 2), are effective in stabilizing the crystal structure.

Experimental

The title compound was prepared by following a reported procedure (Feng et al., 2007). A suspension of 2,4-dichloro-quinazolines (2.0 g, 1 mmol) was stirred in 2% aqueous sodium hydroxide solution (3 ml) for 3 h. Reaction mixture was diluted with water (6 ml) and filtered to remove unreacted 2,4-dichloroquinazoline. Filtrate was neutralized with dilute acetic acid, precipitate thus obtained was filtered and washed with water. The product was recrystallized from acetone / ethyl acetate (5:1) over 5 d at ambient temperature, gave colourless single crystals of 2-chloroquinazolin-4(3H)-one, suitable for X-ray analysis.

Refinement

The H atoms based on C atoms were positioned geometrically at distances C–H = 0.93Å and constrained to ride on their parent atoms with U_iso(H) = 1.2U_eq(C). The amino H atom was found from different Fourier map and refined isotropically.

Figures

Fig. 1.

The molecular structure of title compound with the atom numbering scheme. Displacement ellipsoids are drawn with 50% probability level. H atoms are presented as spheres of arbitrary radius.

Fig. 2.

A packing diagram for title compound. Dashed lines indicate hydrogen bonds.

Crystal data

C8H5ClN2O	F(000) = 736
Mr = 180.59	Dx = 1.625 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2442 reflections
a = 22.4315 (16) Å	θ = 1.9–27.9°
b = 3.7666 (6) Å	µ = 0.46 mm−1
c = 18.0640 (13) Å	T = 113 K
β = 104.682 (7)°	Prism, colourless
V = 1476.4 (3) Å3	0.20 × 0.18 × 0.14 mm
Z = 8

Data collection

Rigaku Saturn CCD diffractometer	1749 independent reflections
Radiation source: rotating anode	1430 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.038
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 1.9°
ω and φ scans	h = −28→27
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −4→4
Tmin = 0.914, Tmax = 0.939	l = −23→23
6933 measured reflections

Refinement

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) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0578P)2] where P = (Fo2 + 2Fc2)/3
1749 reflections	(Δ/σ)max < 0.001
113 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.087385 (18)	0.57099 (12)	0.36030 (2)	0.02301 (15)
O1	0.25626 (5)	0.5555 (3)	0.58943 (6)	0.0200 (3)
N1	0.07663 (6)	0.3042 (4)	0.48893 (7)	0.0178 (3)
N2	0.17290 (6)	0.5527 (4)	0.48745 (7)	0.0165 (3)
C1	0.11297 (7)	0.4595 (4)	0.45572 (9)	0.0164 (3)
C2	0.10115 (7)	0.2222 (4)	0.56609 (8)	0.0155 (3)
C3	0.06280 (7)	0.0601 (4)	0.60639 (9)	0.0183 (3)
H3	0.0211	0.0084	0.5814	0.022*
C4	0.08592 (7)	−0.0240 (4)	0.68250 (9)	0.0186 (3)
H4	0.0597	−0.1318	0.7098	0.022*
C5	0.14730 (7)	0.0467 (4)	0.72020 (9)	0.0179 (3)
H5	0.1626	−0.0140	0.7726	0.021*
C6	0.18533 (7)	0.2042 (4)	0.68100 (9)	0.0172 (3)
H6	0.2272	0.2508	0.7063	0.021*
C7	0.16281 (6)	0.2959 (4)	0.60432 (8)	0.0144 (3)
C8	0.20165 (7)	0.4738 (4)	0.56241 (9)	0.0166 (3)
H1	0.1956 (9)	0.652 (6)	0.4567 (11)	0.042 (6)*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Cl1	0.0253 (2)	0.0286 (3)	0.0141 (2)	−0.00270 (16)	0.00309 (15)	0.00145 (16)
O1	0.0127 (5)	0.0272 (6)	0.0195 (6)	−0.0031 (5)	0.0029 (4)	0.0031 (5)
N1	0.0165 (6)	0.0217 (7)	0.0150 (6)	−0.0028 (5)	0.0036 (5)	−0.0015 (6)
N2	0.0151 (6)	0.0201 (7)	0.0154 (6)	−0.0020 (5)	0.0061 (5)	−0.0002 (5)
C1	0.0171 (7)	0.0178 (8)	0.0136 (7)	0.0007 (6)	0.0028 (6)	−0.0023 (6)
C2	0.0166 (7)	0.0153 (8)	0.0147 (7)	0.0003 (6)	0.0040 (6)	−0.0022 (6)
C3	0.0152 (7)	0.0207 (8)	0.0196 (8)	−0.0032 (6)	0.0054 (6)	−0.0016 (7)
C4	0.0200 (8)	0.0203 (8)	0.0177 (8)	−0.0016 (6)	0.0087 (6)	−0.0003 (6)
C5	0.0220 (8)	0.0177 (8)	0.0141 (7)	0.0021 (6)	0.0047 (6)	0.0004 (6)
C6	0.0148 (7)	0.0178 (8)	0.0182 (7)	−0.0001 (6)	0.0028 (6)	−0.0020 (6)
C7	0.0145 (7)	0.0132 (8)	0.0161 (7)	0.0004 (6)	0.0049 (6)	−0.0021 (6)
C8	0.0174 (7)	0.0157 (8)	0.0176 (7)	0.0014 (6)	0.0060 (6)	−0.0010 (6)

Geometric parameters (Å, º)

Cl1—C1	1.7249 (16)	C3—C4	1.378 (2)
O1—C8	1.2370 (18)	C3—H3	0.9500
N1—C1	1.2706 (19)	C4—C5	1.398 (2)
N1—C2	1.3971 (19)	C4—H4	0.9500
N2—C1	1.3669 (19)	C5—C6	1.374 (2)
N2—C8	1.3766 (19)	C5—H5	0.9500
N2—H1	0.92 (2)	C6—C7	1.392 (2)
C2—C3	1.400 (2)	C6—H6	0.9500
C2—C7	1.408 (2)	C7—C8	1.455 (2)
C1—N1—C2	115.79 (13)	C3—C4—H4	119.4
C1—N2—C8	121.52 (13)	C5—C4—H4	119.4
C1—N2—H1	119.1 (12)	C6—C5—C4	119.64 (14)
C8—N2—H1	119.2 (12)	C6—C5—H5	120.2
N1—C1—N2	126.93 (14)	C4—C5—H5	120.2
N1—C1—Cl1	119.55 (12)	C5—C6—C7	120.25 (14)
N2—C1—Cl1	113.53 (11)	C5—C6—H6	119.9
N1—C2—C3	118.46 (13)	C7—C6—H6	119.9
N1—C2—C7	122.36 (14)	C6—C7—C2	120.18 (14)
C3—C2—C7	119.18 (14)	C6—C7—C8	121.19 (13)
C4—C3—C2	119.58 (14)	C2—C7—C8	118.62 (14)
C4—C3—H3	120.2	O1—C8—N2	120.31 (14)
C2—C3—H3	120.2	O1—C8—C7	124.97 (14)
C3—C4—C5	121.16 (14)	N2—C8—C7	114.72 (13)
C2—N1—C1—N2	0.1 (2)	C5—C6—C7—C8	177.88 (14)
C2—N1—C1—Cl1	179.76 (11)	N1—C2—C7—C6	−179.03 (14)
C8—N2—C1—N1	1.8 (3)	C3—C2—C7—C6	0.8 (2)
C8—N2—C1—Cl1	−177.85 (11)	N1—C2—C7—C8	2.0 (2)
C1—N1—C2—C3	178.19 (13)	C3—C2—C7—C8	−178.21 (13)
C1—N1—C2—C7	−2.0 (2)	C1—N2—C8—O1	178.72 (13)
N1—C2—C3—C4	179.88 (14)	C1—N2—C8—C7	−1.7 (2)
C7—C2—C3—C4	0.1 (2)	C6—C7—C8—O1	0.5 (2)
C2—C3—C4—C5	−0.6 (2)	C2—C7—C8—O1	179.48 (15)
C3—C4—C5—C6	0.3 (2)	C6—C7—C8—N2	−179.07 (14)
C4—C5—C6—C7	0.5 (2)	C2—C7—C8—N2	−0.1 (2)
C5—C6—C7—C2	−1.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1i	0.92 (2)	1.88 (2)	2.7840 (17)	166.5 (19)
C3—H3···N1ii	0.95	2.53	3.449 (2)	163

Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) −x, −y, −z+1.