10-Methoxy­benzo[g]imidazo[1,2-a][1,8]naphthyridine-4-carbonitrile

Andrii V Tarasov; Tatyana A Volovnenko; Noël Lugan; Yulian M Volovenko

doi:10.1107/S1600536809037544

. 2009 Sep 26;65(Pt 10):o2524–o2525. doi: 10.1107/S1600536809037544

10-Methoxybenzo[g]imidazo[1,2-a][1,8]naphthyridine-4-carbonitrile

Andrii V Tarasov ^a,^*, Tatyana A Volovnenko ^a, Noël Lugan ^b, Yulian M Volovenko ^a

PMCID: PMC2970372 PMID: 21577970

Abstract

In the title compound, C₁₆H₁₀N₄O, both the methoxy and nitrile substituents lie in the plane defined by the benzo[g]imidazo[1,2-a]-1,8-naphthyridine ring system, resulting in a nearly planar geometry for the entire molecule (r.m.s. deviation of the non-H atoms from the mean plane is 0.044 Å). In the solid-state, the molecules form a three-dimensional polymer through intermolecular C—H⋯N and C—H⋯O hydrogen bonds. In addition, the packing mode results in stabilizing π–π stacking interactions between the asymmetric units.

Related literature

For the synthesis of the title compound and a series of similar products, see: Volovnenko et al. (2009 ▶). For related compounds and their antibacterial or photophysical properties, see: Kondo et al. (1990 ▶); Gokhale & Seshadri (1987 ▶); Rajagopal & Seshadri (1991 ▶); Vijila et al. (2000 ▶). For the solid-state structures of other imidazonaphthyridine derivatives, see: Fun et al. (1996 ▶); Sivakumar et al. (1996a ▶,b ▶); Muthamizhchelvan et al. (2005a ▶,b ▶). For general metrical features within organic compounds, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₀N₄O
M _r = 274.28
Monoclinic,
a = 7.710 (2) Å
b = 11.970 (2) Å
c = 13.340 (3) Å
β = 93.55 (3)°
V = 1228.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 180 K
0.40 × 0.40 × 0.35 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.95, T _max = 0.97
45253 measured reflections
3532 independent reflections
2507 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.164
S = 1.08
3532 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker (2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809037544/fj2229sup1.cif

e-65-o2524-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037544/fj2229Isup2.hkl

e-65-o2524-Isup2.hkl^{(169.7KB, 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
C8—H8⋯O1ⁱ	0.93	2.50	3.366 (3)	156
C3—H3⋯N1ⁱⁱ	0.93	2.62	3.394 (2)	141

Open in a new tab

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

Table 2. π–π stacking interactions (Å, °).

Cg_i	Cg_j	Centroid distance	Interplanar spacing ⁱ	αⁱⁱ	γⁱⁱⁱ
Cg1	Cg2^iv	3.487 (2)	3.322	2.68	15.42
Cg2	Cg1^iv	3.487 (2)	3.361	2.68	17.68
Cg3	Cg3^iv	3.710 (2)	3.382	0.00	24.27
Cg1	Cg4^v	3.689 (2)	3.336	5.01	25.28
Cg4	Cg1^v	3.689 (2)	3.397	5.01	22.98

Open in a new tab

Notes: (i) perpendicular distance between the centroid of the first ring and the plane of the second ring; (ii) dihedral angle between the plane of the first ring and the plane of the second ring; (iii) angle between the centroid of the first ring and the normal to the plane of the second ring; (iv) symmetry code: Inline graphic ; (v) symmetry code: . Cg1 is the centroid of atoms N1/C1/N2/C13/C14, Cg2 is the centroid of atoms N3/C12/C4–C6/C11, Cg3 is the centroid of atoms N2/C1–C4/C12 and Cg4 is the centroid of atoms C6–C11.

Acknowledgments

This research was performed within the framework of the GDRI ‘Franco–Ukrainian association of Molecular Chemistry’.

supplementary crystallographic information

Comment

New heterocyclic nitrogen-containing systems are always of great interest to synthetic as well as pharmaceutical organic chemists. We have recently reported an efficient and versatile route to benzo[g]imidazo[1,2-a]-1,8-naphthyridines upon thermal reaction of 2-chloroquinoline-3-carbaldehydes with 1-substitued hetarylacetonitriles (Volovnenko et al., 2009). Here we report the crystal structure of the one of synthesized compound, namely, 10-methoxybenzo[g]imidazo[1,2-a]-1,8-naphthyridine-4-carbonitrile. It has been reported that products with similar structures possess not only antibacterial activity (Kondo et al., 1990) but also interesting photophysical properties (Gokhale & Seshadri, 1987; Rajagopal & Seshadri, 1991; Vijila et al., 2000).

Fig. 1 shows a perspective view of the asymetric unit of the title compound, including the labelling scheme. Selected bond distances and angles are given in Table 1. The benzo[g]imidazo[1,2-a]-1,8-naphthyridine core is almost planar (RMS deviation of C1>C14 and N1>N3 from mean plane is 0.035 Å). In addition, both methoxy and carbonitrile substituents attached to C(2) and C(11), respectively, are oriented in such a way that they both lay in heterocyle plane granting a nearly planar geometry to the entire molecule (RMS deviation of the all non-hydrogen atoms from mean plane is 0.044 Å). Bond distances and angles in the title compound are normal (Allen et al., 1987) and compare well with other imidazonaphtyridines derivatives (Fun et al., 1996; Sivakumar et al..1996a,b; Muthamizhchelvan et al., 2005a,b).

The crystal structure is stabilized by C—H···N and C—H···O intermolecular hydrogen bonds (Table 1) forming a three dimensional polymeric structure (Figure 2). In addition, the asymmetric units are seen to be stacked along the (100) axis with relatively short interplanar distances (Table 3) possibly allowing additional stabilization through π–π stacking interactions (Figure 3).

Experimental

The title compound was synthesized by the reaction of 2-chloro-8-methoxyquinoline-3-carbaldehyde (2 mmol) with (1-benzyl-1H-imidazol-2-yl)acetonitrile (2 mmol) in dimethylformamide (3 ml). After refluxing for 1 h, the reaction mixture was left to stand overnight. The resulting crude solid was filtered, washed twice with acetone (10 ml) and dried. Yield: 96%. Crystals suitable for X-ray analysis were obtained by slow crystallization from hot dimethylformamide.