2-Chloro­quinazolin-4(3H)-one

Cao, D.-L.; Yan, F.-Y.; Wang, M.; Li, C.-Y.; Chen, L.

doi:10.1107/S1600536812022891

organic compounds

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Volume 68| Part 6| June 2012| Page o1958

doi:10.1107/S1600536812022891

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2-Chloroquinazolin-4(3H)-one

Dong-Lei Cao,^a Fan-Yong Yan,^b ^* Meng Wang,^a Chu-Ying Li ^b and Li Chen ^a

^aSchool of Materials Science and Engineering, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China, and ^bSchool of Environment & Chemical Engineering, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China
^*Correspondence e-mail: yfytju@yahoo.com

(Received 8 April 2012; accepted 19 May 2012; online 31 May 2012)

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, C 2/c
a = 22.4315 (16) Å
b = 3.7666 (6) Å
c = 18.0640 (13) Å
β = 104.682 (7)°
V = 1476.4 (3) Å³
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[F² > 2σ(F²)] = 0.036
wR(F²) = 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

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

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812022891/rk2353sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022891/rk2353Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022891/rk2353Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Computing details top

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

Figures top

	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.

2-Chloroquinazolin-4(3H)-one top

Crystal data top

C₈H₅ClN₂O	F(000) = 736
M_r = 180.59	D_x = 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 top

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

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)] = 0.036	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(F_o²) + (0.0578P)²] where P = (F_o² + 2F_c²)/3
1749 reflections	(Δ/σ)_max < 0.001
113 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₈H₅ClN₂O	V = 1476.4 (3) Å³
M_r = 180.59	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.4315 (16) Å	µ = 0.46 mm⁻¹
b = 3.7666 (6) Å	T = 113 K
c = 18.0640 (13) Å	0.20 × 0.18 × 0.14 mm
β = 104.682 (7)°

Data collection top

Rigaku Saturn CCD diffractometer	1749 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	1430 reflections with I > 2σ(I)
T_min = 0.914, T_max = 0.939	R_int = 0.038
6933 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.45 e Å⁻³
1749 reflections	Δρ_min = −0.23 e Å⁻³
113 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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) top

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) top

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.

Experimental details

Crystal data
Chemical formula	C₈H₅ClN₂O
M_r	180.59
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	113
a, b, c (Å)	22.4315 (16), 3.7666 (6), 18.0640 (13)
β (°)	104.682 (7)
V (Å³)	1476.4 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.20 × 0.18 × 0.14

Data collection
Diffractometer	Rigaku Saturn CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.914, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	6933, 1749, 1430
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.095, 1.03
No. of reflections	1749
No. of parameters	113
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.23

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2006).

Hydrogen-bond geometry (Å, º) top

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)	163.3

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

References

Feng, J., Zhang, Z. Y., Wallace, M. B., Stafford, J. A., Kaldor, S. W., Kassel, D. B., Navre, M., Shi, L. H., Skene, R. J., Asakawa, T., Takeuchi, K., Xu, R. D., Webb, D. R. & Gwaltney, S. L. (2007). J. Med. Chem. 50, 2297–2300. Web of Science CrossRef PubMed CAS Google Scholar
Labuda, J., Ovadekova, R. & Galandova, J. (2009). Mikrochim. Acta, 164, 371–377. Web of Science CrossRef CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC INc., The Woodlands, Texas, USA. Google Scholar
Rigaku/MSC (2006). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1958

doi:10.1107/S1600536812022891

Open

access