2-(1H-indol-3-ylcarbon­yl)acetonitrile

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

doi:10.1107/S1600536809001342

. 2009 Feb 4;65(Pt 3):o447. doi: 10.1107/S1600536809001342

2-(1H-indol-3-ylcarbonyl)acetonitrile

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

PMCID: PMC2968615 PMID: 21582120

Abstract

The title compound, C₁₁H₈N₂O, crystallizes with two crystallographically independent molecules in the asymmetric unit which are approximately perpendicular to each other [79.97 (6)°]. The indole ring system is planar [r.m.s. deviation = 0.010 (1) Å]. The crystal structure is stabilized by intermolecular C—H⋯N and N—H⋯O interactions.

Related literature

For the use of indole derivatives as bioactive drugs, see: Stevenson et al. (2000 ▶). For their biological properties, see: Harris & Uhle (1960 ▶); Ho et al. (1986 ▶). For their high aldose reductase inhibitory activity, see: Rajeswaran et al. (1999 ▶). For a related structure, see: Ramesh et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₁H₈N₂O
M _r = 184.19
Triclinic,
a = 7.3439 (2) Å
b = 7.3534 (2) Å
c = 18.2475 (5) Å
α = 83.402 (2)°
β = 78.890 (2)°
γ = 73.501 (1)°
V = 925.23 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.974, T _max = 0.983
18838 measured reflections
3253 independent reflections
2717 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.100
S = 1.06
3253 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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/S1600536809001342/bt2839sup1.cif

e-65-0o447-sup1.cif^{(20.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001342/bt2839Isup2.hkl

e-65-0o447-Isup2.hkl^{(156.3KB, 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—H1⋯O1ⁱ	0.86	1.98	2.8146 (18)	163
C2—H2⋯N13ⁱ	0.93	2.59	3.236 (2)	127
N1′—H1′⋯O1′ⁱⁱ	0.86	2.00	2.8166 (15)	158

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

Acknowledgments

PR thanks Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection.

supplementary crystallographic information

Comment

Indole derivatives are used as bioactive drugs (Stevenson et al., 2000) and they exibit anti-allergic, central nervous system depressant and muscle relaxant properties (Harris & Uhle 1960; Ho et al., 1986). Indoles have been proved to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999). Against this background and to ascertain the molecular conformation, the structure determination of the title compound has been carried out.

There are two crystallographically independent molecules in the asymmetric unit and they are approximately perpendicular to each other [79.97 (6)°]. In both molecules the indole ring systems are planar and the sum of the angles at N1 (359.95°) and N1' (359.94°) are in accordance with sp² hybridization. The bond angles of the cyano group [179.8 (2) and 179.6 (2)°] in both molecules show their linear character. The C≡N bond distances [1.133 (2) and 1.131 (2) Å] are comparable with the literature values (Ramesh et al., 2008).

The crystal packing is covered by C—H···N, C—H···O and C—H···π types intermolecular interactions in addition to van der Waals forces. N1 atom in one of the molecules donates one proton to O1 (-1 + x, y, z) which connects the molecules into a one dimensional C6 chain (Bernstein et al., 1995) running along the a axis, whereas in the other molecule at N1' forms similar network with O1' (x, 1 + y, z) along the b axis. The combination of N1—H1···O1 and C2—H2···N13 hydrogen bonds form a R₂² (9) dimer chain running along the a axis.

Experimental

Indole (5.85 g, 50 mmol) was added to a solution prepared by dissolution of cyanoacetic acid (5.0 g, 50 mmol) in Ac₂O (50 ml) at 50 °C. The solution was heated at 85 °C for 5 min. During that period 3-cyanoacetylindole started to crystallize. After 5 more min, the mixture was allowed to cool and the solid was collected, washed with MeOH, and dried.