N′-[(E)-Benzyl­idene]-1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbohydrazide

Farah Deeba; Misbahul Ain Khan; Muhammad Zia-ur-Rehman; Ertan Şahin; Nagihan Çaylak

doi:10.1107/S1600536809048739

. 2009 Nov 21;65(Pt 12):o3152–o3153. doi: 10.1107/S1600536809048739

N′-[(E)-Benzylidene]-1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbohydrazide

Farah Deeba ^a, Misbahul Ain Khan ^b, Muhammad Zia-ur-Rehman ^a,^*, Ertan Şahin ^c, Nagihan Çaylak ^d

PMCID: PMC2972033 PMID: 21578871

Abstract

In the title compound, C₁₉H₁₈N₄O₂, the 1,8-naphthyridine ring system is essentially planar [r.m.s. deviation = 0.011 (3) Å]. The dihedral angle between the naphthyridine ring system and the phenyl ring is 28.95 (7)°. The carbohydrazide H atom is involved in an intramolecular N—H⋯O hydrogen bond, forming a six-membered hydrogen-bonded ring. In the crystal, the molecules arrange themselves into centrosymmetric dimers by means of intermolecular C—H⋯O hydrogen bonds.

Related literature

For the synthesis of heterocyclic compounds, see: Chen et al. (2001 ▶); Zia-ur-Rehman et al. (2006 ▶, 2009 ▶). For their biological activity, see: Ferrarini et al. (2000 ▶); Hoock et al. (1999 ▶); Nakatani et al. (2001 ▶); Roma et al. (2000 ▶). For related structures, see: Catalano et al. (2000 ▶); Deeba et al. (2009 ▶). graphic file with name e-65-o3152-scheme1.jpg

Experimental

Crystal data

C₁₉H₁₈N₄O₂
M _r = 334.37
Triclinic,
a = 7.1642 (1) Å
b = 8.8383 (1) Å
c = 14.4560 (2) Å
α = 82.624 (6)°
β = 85.454 (7)°
γ = 68.594 (5)°
V = 844.63 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: multi-scan (Blessing, 1995 ▶) T _min = 0.983, T _max = 0.991
18153 measured reflections
3446 independent reflections
2105 reflections with I > 2σ(I)
R _int = 0.066

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.175
S = 1.03
3446 reflections
236 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809048739/is2485sup1.cif

e-65-o3152-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048739/is2485Isup2.hkl

e-65-o3152-Isup2.hkl^{(165.5KB, 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
N1—H1N⋯O1	0.89 (3)	1.93 (2)	2.674 (3)	140 (2)
C7—H7B⋯O2ⁱ	0.97	2.45	3.204 (3)	134
C9—H9⋯O2ⁱ	0.93	2.51	3.340 (3)	149

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are indebted to the Department of Chemistry and Atatürk University, Turkey, for the use of the X-ray diffractometer purchased under grant No. 2003/219 from the University Research Fund.

supplementary crystallographic information

Comment

1,8-Naphthyridines have been cited in the literature for their medical uses such as antibacterial (Chen et al., 2001), anti-inflammatory (Roma et al., 2000), anti-hypertensive and anti-platelet activities (Ferrarini et al., 2000) agents. Besides few among these have been reported to be excellent fluorescent markers of nucleic acids (Hoock et al., 1999) and probe molecules (Nakatani et al., 2001). In continuation of our work on the synthesis, biological activity and crystal structures of various heterocyclic compounds (Zia-ur-Rehman et al., 2006, 2009), we herein report the synthesis and crystal structure of the title compound (I) (Fig. 1).

The structure of the adjoined pyridine rings comprising of the naphthyridine ring is planar while carbonyl oxygen O1 on C11 is involved in intramolecular hydrogen bonding with N1H, giving rise to a six-membered hydrogen bond ring (Table 1). All bond distances are essentially identical to those found in the literature (Catalano et al., 2000; Deeba et al., 2009). Each molecule forms centrosymmetric dimer through intermolecular C—H···O hydrogen bonds, giving rise the formation of two six-membered hydrogen bond rings per dimer (Fig. 2).

Experimental

A mixture of 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbohydrazide (10.0 mmol, 2.46 g), benzaldehyde (11.0 mmol, 1.17 g), ortho phosphoric acid (2 drops) and ethyl alcohol (20.0 ml) was refluxed for a period of two hours. After completion of the reaction as indicated by TLC, three fourth of the solvent was evaporated and the contents were cooled to room temperature. Crystals obtained were washed with cold ethanol and dried; Yield: 89%.