4-(4-Bromo­phen­yl)-6-(1H-indol-3-yl)-2,2′-bipyridine-5-carbonitrile

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

doi:10.1107/S1600536809001354

. 2009 Feb 4;65(Pt 3):o450. doi: 10.1107/S1600536809001354

4-(4-Bromophenyl)-6-(1H-indol-3-yl)-2,2′-bipyridine-5-carbonitrile

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

PMCID: PMC2968551 PMID: 21582123

Abstract

In the title compound, C₂₅H₁₅BrN₄, the two pyridine rings lie in a common plane [r.m.s. deviation = 0.023 (2) Å], whereas the bromophenyl and indole rings are twisted away from this plane by 52.82 (12) and 28.02 (10)°, respectively. The crystal structure is stabilized by intermolecular N—H⋯N interactions.

Related literature

Compounds having an indole ring system have been shown to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶);

Experimental

Crystal data

C₂₅H₁₅BrN₄
M _r = 451.32
Orthorhombic,
a = 14.7393 (4) Å
b = 10.7465 (3) Å
c = 25.4251 (7) Å
V = 4027.23 (19) Å³
Z = 8
Mo Kα radiation
μ = 2.06 mm⁻¹
T = 293 (2) K
0.29 × 0.26 × 0.22 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.556, T _max = 0.635
47903 measured reflections
5545 independent reflections
3138 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.120
S = 0.99
5545 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.58 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/S1600536809001354/bt2842sup1.cif

e-65-0o450-sup1.cif^{(22.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001354/bt2842Isup2.hkl

e-65-0o450-Isup2.hkl^{(266.1KB, 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
N14—H14⋯N17ⁱ	0.86	2.22	2.980 (3)	147

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

Compounds having indole ring system are proved to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999). Against this background and to ascertain the detailed conformation, the crystal structure determination of the title compound has been carried out.

The ORTEP diagram of the title compound is shown in Fig. 1. The two pyridine rings lie in the same plane as can be seen from the dihedral angle of 3.61 (13)°. The bromophenyl and indole rings are twisted away from the bipyridine ring by 52.82 (12)° and 28.02 (10)°, respectively. The sum of the bond angles at N14 (360.0°) in the indole ring is in accordance with sp² hybridization. The bond angle of C3—C16—N17 [178.4 (3)°] shows the linearity of the cyano group, a feature observed in carbonitrile compounds.

The crystal packing is controlled by C—H···N intermolecular interactions in addition to van der Waals forces. Atom N14 (x, y, z) donates one proton to N17 at (-x + 1,-y,-z + 1) which connects the molecules to form a R₂² (16) dimer (Bernstein et al., 1995).

Experimental

A mixture of 3-cyanoacetyl indole (1 mmol), 4-bromobenzaldehyde (1 mmol) and 2-acetyl pyridine (1 mmol) in 5 gm of ammonium acetate under neat condition was refluxed 6–8 hrs. 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 80% yield (90:10, petroleum ether: ethyl acetate) and recrystallized in ethanol.