2-(2-Chloro­phen­yl)-2,3-dihydro­quinazolin-4(1H)-one

Ming-Jian Li; Chang-Jun Feng

doi:10.1107/S1600536809031328

. 2009 Aug 15;65(Pt 9):o2145. doi: 10.1107/S1600536809031328

2-(2-Chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one

Ming-Jian Li ^a, Chang-Jun Feng ^a,^*

PMCID: PMC2970036 PMID: 21577554

Abstract

The title compound, C₁₄H₁₁ClN₂O, was synthesized by the reaction of 2-chlorobenzaldehyde and 2-aminobenzamide 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 molecules 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 _r = 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
Δρ_max = 0.20 e Å⁻³
Δρ_min = −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.

Supplementary Material

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

e-65-o2145-sup1.cif^{(17.4KB, cif)}

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

e-65-o2145-Isup2.hkl^{(108.3KB, hkl)}

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—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)

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

Acknowledgments

We are grateful to the National Natural Science Foundation of China (20776149) and the Natural Science Foundation (XKY2008313) of Xuzhou Institute of Technology for financial support.

supplementary crystallographic information

Comment

Quinazoline derivatives are well known compounds as antitumor agents (Feng et al., 2006; Keenan et al., 2004; Mikiciuk-Olasik et al., 2004). In addition, it was reported that some quinazoline derivatives possessed biological activities, such as antimalarial activity (Lin et al., 2006) antibacterial activity (Bedi et al., 2004) and antifungal activity (Saleh et al., 2004). We report here the crystal structure of 2-(2-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one, (I).

The X-ray crystal structure determination indicates that the pyrimidine ring in the quinazoline moiety is slightly distorted, adopting a skew-boat conformation. The atoms of C2, C3, C8 and N2 are coplanar, with the atoms N1 and C1 deviating from the defined plane by 0.256 (2) and 0.623 (2) Å, respectively. The basal plane is nearly parallel to the benzene ring (C3—C8), forming a dihedral angle of 5.4 (1) °. And is nearly perpendicular to the benzene ring (C9—C14), forming a dihedral angle of 87.7 (1) °. Two benzene rings make a dihedral angle of 87.1 (1) °.

The hydrogen bonds of N—H···O and C—H···N are presented in the crystal structure of (I) (Table 2). The intermolecular hydrogen bond (N1—H1A···O1) and hydrogen bond (C1—H1B···N2) link the adjacent molecules, forming dimmers, respectively. The hydrogen bond of N2—H2A···O1 and above hydrogen bonds link the molecules forming polymers along b (Figure 2).

Experimental

The title compound, (I), was prepared by the reaction of 2-chlorobenzaldehyde (2 mmol, 0.280 g), 2-aminobenzamide (2 mmol, 0.272 g) and ionic liquid of [Bmim]Br (2 ml) at 353 K. The isolated compound melts at 485–486 K. The single crystals suitable for X-ray diffraction were obtained by slow evaporation ethanol solution.