3-[(2-Chloro-6-methyl­quinolin-3-yl)meth­yl]quinazolin-4(3H)-one

S Mohana Roopan; F Nawaz Khan; Sriramakrishnaswamy Kone; Venkatesha R Hathwar; Mehmet Akkurt

doi:10.1107/S1600536810020830

. 2010 Jun 5;66(Pt 7):o1545. doi: 10.1107/S1600536810020830

3-[(2-Chloro-6-methylquinolin-3-yl)methyl]quinazolin-4(3H)-one

S Mohana Roopan ^a, F Nawaz Khan ^a, Sriramakrishnaswamy Kone ^a, Venkatesha R Hathwar ^b, Mehmet Akkurt ^c,^*

PMCID: PMC3006817 PMID: 21587791

Abstract

In the title molecule, C₁₉H₁₄ClN₃O, the quinoline and quinazoline ring systems form a dihedral angle of 80.75 (4)°. In the crystal, the molecules are linked by pairs of C—H⋯N hydrogen bonds into centrosymmetric dimers, generating R ₂ ²(6) ring motifs. The structure is further stabilized by C—H⋯π interactions and π–π stacking interactions [centroid–centroid distances = 3.7869 (8) and 3.8490 (8) Å].

Related literature

For quinoline analogues, see: Roopan et al. (2009 ▶); Khan et al. (2009 ▶, 2010a ▶,b ▶). For quinazolinone analogues, see: Roopan et al. (2008a ▶,b ▶). For the properties and applications of related compounds, see: Abdel-Hamide et al. (1996 ▶); Bekhit & Khalil (1998 ▶); Chapman et al. (1963 ▶); Honda et al. (1979 ▶).

Experimental

Crystal data

C₁₉H₁₄ClN₃O
M _r = 335.78
Monoclinic,
a = 7.86728 (14) Å
b = 14.7098 (3) Å
c = 13.7055 (3) Å
β = 102.1500 (17)°
V = 1550.56 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 295 K
0.25 × 0.21 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur E CCD diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.938, T _max = 0.960
15755 measured reflections
3048 independent reflections
2417 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.096
S = 1.14
3048 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020830/gk2276sup1.cif

e-66-o1545-sup1.cif^{(23.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020830/gk2276Isup2.hkl

e-66-o1545-Isup2.hkl^{(149.6KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the N1/C1–C4/C9 and N2/N3/C12/C13/C18/C19 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯N3ⁱ	0.93	2.51	3.271 (2)	139
C8—H8⋯Cg2ⁱⁱ	0.93	2.89	3.6598 (16)	142
C10—H10A⋯Cg1ⁱⁱⁱ	0.96	2.68	3.5189 (17)	146

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

Acknowledgments

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the FIST–DST program at SSCU, IISc. We also thank Professor T. N. Guru Row, IISc, Bangalore, for his help with the data collection. FNK thanks the DST for Fast Track Proposal funding.

supplementary crystallographic information

Comment

Heterocyclic chemistry comprises at least half of all organic chemistry research worldwide (Roopan et al., 2008a,b). In particular, heterocyclic structures form the basis of many pharmaceutical, agrochemical and veterinary products. 4(3H)-quinazolinones and quinolines (Roopan et al., 2009) are classes of fused heterocycles that are of considerable interest because of their biological properties. Some are endowed with antimicrobial, aniconvulsant, antihistamine and anti-inflammatory properties (Abdel-Hamide et al., 1996, Chapman et al., 1963, Bekhit et al., 1998). On the other hand, some quinoline derivatives also have various biological properties like antioxidant, hemolytic and cytotoxicity. These observations prompted us to synthesized heterocyclic compounds containing a quinolinyl-quinazolinone moiety.

As shown in Fig. 1, the quinoline (N1/C1–C9) and quinazoline (N2/N3/C12–C19) ring systems of the title molecule (I) are almost planar with maximum deviations of -0.016 (1) Å for C2 and 0.065 (1) Å for N2, respectively, and there is a dihedral angle of 80.75 (4)° between them.

Two neighbouring molecules are linked by a pair of C—H···N hydrogen bonds into a pseudo-centrosymmetric dimer, generating an R²₂(6) ring motif (Table 1, Fig. 2). In addition, the structure is stabilized by C—H···π interactions (Table 1) and π-π stacking interactions [Cg1···Cg3(2 - x,-y, 2 - z) = 3.7869 (8) Å and Cg3···Cg3(1 - x, -y, 2 - z) = 3.8490 (8) Å; where Cg1 and Cg3 are centroids of the N1/C1–C4/C9 and C4–C9 rings, respectively].

Experimental

To a solution of 4(3H)-quinazolinone (146 mg, 1 mmol) in 2 ml of DMF were added KOtBu (112 mg, 1 mmol) in 10 ml of THF and 2-chloro-3-(chloromethyl)-6-methylquinoline (225 mg, 1 mmol) and the resulting mixture was refluxed at 343 K for 1 h. After the completion, the reaction was cooled and the excess of solvent removed under reduced pressure. Crushed ice was mixed with the residue. White solid was formed which was purified by column chromatography using hexane and ethylacetate as the eluant. Crystals of suitable quality were grown by solvent evaporation from a solution of the compound in diethyl ether.