6-Chloro-3-phenethyl-2-thioxo-2,3-di­hydro­quinazolin-4(1H)-one

Norhafizah Mohd Hashim; Hasnah Osman; Afidah Abdul Rahim; Chin Sing Yeap; Hoong-Kun Fun

doi:10.1107/S1600536810010330

. 2010 Mar 27;66(Pt 4):o950. doi: 10.1107/S1600536810010330

6-Chloro-3-phenethyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

Norhafizah Mohd Hashim ^a, Hasnah Osman ^a, Afidah Abdul Rahim ^a, Chin Sing Yeap ^b,^‡, Hoong-Kun Fun ^b,^*,^§

PMCID: PMC2984037 PMID: 21580754

Abstract

The asymmetric unit of the title quinazolinone compound, C₁₆H₁₃ClN₂OS, consists of two crystallographically independent molecules, A and B. The dihedral angles between the quinazoline and benzene rings are 16.88 (6) and 32.34 (6)° for molecules A and B, respectively. In the crystal structure, molecules A and B are linked by two bifurcated intermolecular N—H⋯S and C—H⋯S hydrogen bonds. Pairs of molecules are further linked by C—H⋯O and C—H⋯Cl hydrogen bonds into a chain aligned approximately along [110].

Related literature

For the preparation and biological testing of quinazolinone derivatives, see: Glasser et al. (1971 ▶). For the preparation of the title compound, see: Butler & Partridge (1959 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₆H₁₃ClN₂OS
M _r = 316.79
Triclinic,
a = 9.7228 (4) Å
b = 11.8588 (4) Å
c = 14.4983 (5) Å
α = 69.709 (1)°
β = 74.395 (1)°
γ = 67.681 (1)°
V = 1432.19 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 100 K
0.45 × 0.19 × 0.07 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.836, T _max = 0.973
41666 measured reflections
10238 independent reflections
8470 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.155
S = 1.08
10238 reflections
387 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010330/tk2645sup1.cif

e-66-0o950-sup1.cif^{(28.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010330/tk2645Isup2.hkl

e-66-0o950-Isup2.hkl^{(500.6KB, 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
N2A—H2NA⋯S1Bⁱ	0.81 (2)	2.53 (2)	3.3362 (12)	172 (2)
N2B—H2NB⋯S1Aⁱⁱ	0.91 (2)	2.41 (2)	3.3038 (12)	167.8 (19)
C3A—H3AA⋯S1Bⁱ	0.93	2.95	3.7207 (13)	142
C3B—H3BA⋯S1Aⁱⁱ	0.93	2.87	3.6470 (15)	142
C6A—H6AA⋯O1Aⁱⁱⁱ	0.93	2.41	3.2873 (17)	156
C6B—H6BA⋯O1B^iv	0.93	2.44	3.2810 (18)	151
C16A—H16A⋯Cl1Aⁱⁱⁱ	0.93	2.82	3.4630 (15)	127
C16B—H16B⋯Cl1B^iv	0.93	2.85	3.5836 (13)	137

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

Acknowledgments

HO, AAR and NMH thank Universiti Sains Malaysia (USM) and the Malaysian Government for financing this project through an RU Grant (1001/PKIMIA/811016). HKF and CSY thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012). CSY also thanks USM for the award of a USM Fellowship.

supplementary crystallographic information

Comment

Quinazolinones are versatile compounds showing different biological and pharmacological activities. For example, 6-chloro-3-phenyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one has been reported to possess anti-convulsant activity, and a related compound was reported to inhibit maximal electroshock and chemoshock seizures in mice (Glasser et al., 1971).

The asymmetric unit of the title quinazolinone compound, (I), consists of two crystallographically independent molecules, A & B (Fig. 1). The quinazoline rings are essentially planar with maximum derivations of 0.034 (1) Å for atom N1A, and 0.049 (1) Å for atom C8B. The dihedral angles between the quinazoline and benzene rings are 16.88 (6) and 32.34 (6)° for molecules A and B, respectively.

In the crystal structure, molecule A and B are linked together by two bifurcated intermolecular N–H···S and C–H···S hydrogen bonds, Table 1. This pair of molecules is further linked by intermolecular C6A–H6AA···O1A, C16A–H16A···Cl1A, C6B–H6BA···O1B and C16B–H16B···Cl1B hydrogen bonds into a one-dimensional chain (Fig. 2, Table 1).

Experimental

The title compound (I) was synthesized according to a modification of the method of Butler & Partridge (1959). Equimolar amounts of 2-amino-5-chlorobenzoic acid and 2-phenylethyl isothiocyanate in acetic acid (6 ml) were mixed and stirred under reflux at 423 K for 90 min. The solid that formed was the pure thiol (yield 76.7 %) which produced colourless crystals upon recrystallization from 99.5% ethanol.