1-(3-Ethyl­phen­yl)-4,6-dimethyl-2-oxo-1,2-dihydro­pyridine-3-carbonitrile

Mansour S Al-Said; Mostafa M Ghorab; Hazem A Ghabbour; Suhana Arshad; Hoong-Kun Fun

doi:10.1107/S1600536812019927

. 2012 May 12;68(Pt 6):o1679. doi: 10.1107/S1600536812019927

1-(3-Ethylphenyl)-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Mansour S Al-Said ^a, Mostafa M Ghorab ^a, Hazem A Ghabbour ^b, Suhana Arshad ^c, Hoong-Kun Fun ^c,^*,^‡

PMCID: PMC3379275 PMID: 22719473

Abstract

In the title compound, C₁₆H₁₆N₂O, the essentially planar 1,2-dihydropyridine ring [maximum deviation = 0.021 (1) Å] makes a dihedral angle of 85.33 (8)° with the benzene ring. In the crystal, molecules are linked into a chain along the b axis via C—H⋯O interactions.

Related literature

For the biological activities and applications of 2-pyridone derivatives, see: Abadi et al. (2009 ▶); Cheney et al. (2007 ▶); Aqui & Vonderheide (2008 ▶); Ambrosini et al. (1997 ▶); Murata et al. (2001 ▶); Ghorab et al. (2009 ▶, 2010 ▶); Al-Said et al. (2010 ▶). For related structures, see: Lynch & McClenaghan (2002 ▶); Elgemeie & Jones (2004 ▶). graphic file with name e-68-o1679-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₆N₂O
M _r = 252.31
Monoclinic,
a = 8.3834 (3) Å
b = 7.1852 (2) Å
c = 23.5264 (8) Å
β = 93.203 (3)°
V = 1414.93 (8) Å³
Z = 4
Cu Kα radiation
μ = 0.59 mm⁻¹
T = 296 K
0.93 × 0.46 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.609, T _max = 0.960
9742 measured reflections
2638 independent reflections
1938 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.161
S = 1.09
2638 reflections
170 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.18 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 datablock(s) global, I. DOI: 10.1107/S1600536812019927/is5134sup1.cif

e-68-o1679-sup1.cif^{(23.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019927/is5134Isup2.hkl

e-68-o1679-Isup2.hkl^{(129.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812019927/is5134Isup3.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
C4—H4A⋯O1ⁱ	0.93	2.32	3.2105 (18)	161

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful for the sponsorship of the Research Center, College of Pharmacy and the Deanship of Scientific Research, King Saud University, Riyadh, Saudi Arabia. HKF and SA thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). SA thanks the Malaysian Government and USM for the award of Academic Staff Training Scheme (ASTS).

supplementary crystallographic information

Comment

It was reported that compounds containing the 2-pyridone moiety was proven to possess several biological properties, especially anticancer activity (Abadi et al., 2009; Cheney et al., 2007; Aqui & Vonderheide, 2008; Ambrosini et al., 1997; Murata et al., 2001). Compounds containing heteroaromatic rings frequently play an important role as scaffolds of bioactive substances. It is well known that pyridone and its derivatives are among the most popular N-heteroaromatic compounds integrated into the structures of many pharmaceutical compounds and their structural units occur in various molecules exhibiting diverse biological activities (Abadi et al., 2009). Based on the above information and as a continuation of our previous work on anticancer agents (Ghorab et al., 2009; Al-Said et al., 2010; Ghorab et al., 2010), we report the synthesis of a novel 2-pyridone derivative which is expected to exhibit anticancer activity.

In the title compound (Fig. 1), the 1,2-dihydropyridine ring (N1/C1–C5) is essentially planar with a maximum deviation of 0.021 (1) Å at atom N1 and almost perpendicular with the benzene ring (C6–C11) with a dihedral angle of 85.33 (8)°. Bond lengths and angles are within the normal ranges and are comparable to those in the related structures (Lynch & McClenaghan, 2002; Elgemeie & Jones, 2004). The crystal structure is shown in Fig. 2. The molecules are linked into a one-dimensional chain along the b-axis via C4—H4A···O1 interactions (Table 1).

Experimental

A mixture of 2-cyano-N-(3-ethylphenyl)acetamide (1.88 g, 0.01 mol) and acetylacetone (1.00 g, 0.01 mol) in absolute ethanol (50 ml) containing piperidine (0.5 ml) were refluxed for 5 h. The reaction mixture was triturated with ethanol and the solid obtained was recrystallized from ethanol to give the title compound. A single-crystal suitable for an X-ray structural analysis was obtained by slow evaporation from an ethanol solution at room temperature.