4-(2,4-Dichlorophenyl)-2-(1H-indol-3-yl)-6-methoxypyridine-3,5-dicarbonitrile

P Ramesh; A Subbiahpandi; P Thirumurugan; P T Perumal; M N Ponnuswamy

doi:10.1107/S1600536808027670

. 2008 Sep 6;64(Pt 10):o1892. doi: 10.1107/S1600536808027670

4-(2,4-Dichlorophenyl)-2-(1H-indol-3-yl)-6-methoxypyridine-3,5-dicarbonitrile

P Ramesh ^a, A Subbiahpandi ^a, P Thirumurugan ^b, P T Perumal ^b, M N Ponnuswamy ^c,^*

PMCID: PMC2959379 PMID: 21201104

Abstract

In the title compound, C₂₂H₁₂Cl₂N₄O, the indole ring system and the benzene ring form dihedral angles of 21.18 (7)° and 68.43 (8)°, respectively, with the pyridine ring. The methoxy group is coplanar with the pyridine ring. In the crystal structure N—H⋯N intermolecular hydrogen bonds link the molecules into C(10) chains running along [011]. Intramolecular C—H⋯N hydrogen bonds are also observed.

Related literature

For related literature, see: James et al. (1991 ▶); Kobayashi et al. (1991 ▶); Rajeswaran et al. (1999 ▶). For graph-set analysis of hydrogen-bonding patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₂H₁₂Cl₂N₄O
M _r = 419.26
Triclinic,
a = 9.5394 (2) Å
b = 10.0358 (2) Å
c = 11.1739 (3) Å
α = 111.994 (1)°
β = 97.303 (1)°
γ = 93.715 (1)°
V = 976.46 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 298 (2) K
0.58 × 0.40 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.821, T _max = 0.907
10781 measured reflections
3401 independent reflections
3019 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.096
S = 1.05
3401 reflections
267 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); 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: SHELXL97 and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027670/ci2655sup1.cif

e-64-o1892-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027670/ci2655Isup2.hkl

e-64-o1892-Isup2.hkl^{(163.4KB, 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
C9—H9⋯N1	0.93	2.56	3.045 (2)	113
C15—H15⋯N17	0.93	2.56	3.282 (2)	135
N14—H14⋯N25ⁱ	0.83 (2)	2.22 (2)	2.996 (2)	156 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

PR thanks V. Ramkumar, Department of Chemistry, IIT-Madras, Chennai, India, for his help with the data collection.

supplementary crystallographic information

Comment

Spiro compounds are the naturally occurring substances which exibit many biological properties (Kobayashi et al., 1991; James et al., 1991). Indoles have been proved to display high aldose reductase inhibitory activity (Rajeswaran et al.., 1999). In view of this an X-ray diffraction study of the title compound was carrid out.

The indole ring system is essentially planar. The indole ring system and the benzene ring form dihedral angles of 21.18 (7)° and 68.43 (8)°, respectively, with the pyridine ring. The methoxy group is coplanar with the pyridine ring, with the C26—O1—C6—N1 torsion angle being 4.9 (2)°. C—H···N type intramolecular hydrogen bonds are observed in the molecular structure.

In the crystal structure N—H···N intermolecular hydrogen bonds link the molecules into C(10) chains (Bernstein et al., 1995) running along the [0 1 1].

Experimental

A mixture of 3-cyanoacetyl indole (1 mmol), 2,4 dichlorobenzaldehyde (1 mmol) and sodium hydroxide (1.2 mmol) in methanol was refluxed. After 15 min malanonitrile (1 mmol) was added and the reflux was continued for 4 h. After the completion of the reaction (as monitored by TLC), it was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuo. The crude product was chromatographed and isolated in 78% yield (90:10, petroleum ether: ethyl acetate). The crude product was recrystallized in ethanol.