Crystal structure of 2-(4-chloro­phen­yl)-4-(1H-indol-3-yl)-6-phenyl­pyridine-3-carbo­nitrile

R Vishnupriya; J Suresh; Pethaiah Gunasekaran; Subbu Perumal; P L Nilantha Lakshman

doi:10.1107/S1600536814017693

. 2014 Aug 6;70(Pt 9):o978. doi: 10.1107/S1600536814017693

Crystal structure of 2-(4-chlorophenyl)-4-(1H-indol-3-yl)-6-phenylpyridine-3-carbonitrile

R Vishnupriya ^a, J Suresh ^a, Pethaiah Gunasekaran ^b, Subbu Perumal ^b, P L Nilantha Lakshman ^c,^*

PMCID: PMC4186124 PMID: 25309290

Abstract

In the title compound, C₂₆H₁₆ClN₃, the dihedral angles between the central pyridine ring and the pendant phenyl, chlorobenzene and indole rings are 18.52 (12), 48.97 (11) and 21.20 (10)°, respectively. An intramolecular C—H⋯N_c (c = cyanide) hydrogen bond occurs. In the crystal, inversion dimers linked by pairs of N—H⋯N_c hydrogen bonds generate R ₂ ²(16) loops.

Keywords: crystal structure, pyridine-3-carbonitrile, hydrogen bonding

Related literature

For the biological activity of substituted pyridine derivatives, see: Yao et al. (1994 ▶). For a related structure, see: Vishnupriya et al. (2014 ▶).

Experimental

Crystal data

C₂₆H₁₆ClN₃
M _r = 405.87
Monoclinic,
a = 7.6533 (4) Å
b = 11.4822 (7) Å
c = 23.2906 (14) Å
β = 94.351 (1)°
V = 2040.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.50 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.958, T _max = 0.986
15210 measured reflections
4194 independent reflections
3000 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.146
S = 1.04
4194 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.40 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814017693/hb7263sup1.cif

e-70-0o978-sup1.cif^{(21.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017693/hb7263Isup2.hkl

e-70-0o978-Isup2.hkl^{(201.4KB, hkl)}

Click here for additional data file.^{(7.3KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814017693/hb7263Isup3.cml

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S1600536814017693/hb7263fig1.tif

The molecular structure of compound showing 30% probability displacement ellipsoids.

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S1600536814017693/hb7263fig2.tif

Partial packing view of the compound showing molecules linked by a pair of N—H⋯N interactions (dotted lines).

CCDC reference: 1017501

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C58—H58⋯N2	0.93	2.58	3.285 (4)	133
N3—H3⋯N2ⁱ	0.86	2.20	3.037 (3)	164

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Symmetry code: (i) Inline graphic .

Acknowledgments

JS and RV thank the management of the Madura College for their encouragement and support. SP thanks the Department of Science and Technology, New Delhi, for a major research project (SR/S1/OC/-50/2011) and the University Grants Commission, New Delhi, for the award of a BSR Faculty Fellowship

supplementary crystallographic information

S1. Comment

Thienopyridines have been used as antithrombotic agents (Yao et al., 1994) against platelet aggregation. As part of our ongoing studies in this area (Vishnupriya et al., 2014) the title compound was investigated.

The deviation of the nitrile atoms (C41,N2) from the mean plane of the pyridine ring system is 0.0579 (5) and 0.0826 (2) Å. The shortening of the C—N distances [1.340 (3) and 1.348 (3) Å] and the opening of the N1–C4–C5 angle [120.83 (2)°] may be attributed to the size of the substituent at C1, correlating well with the values observed in the ortho-substituted derivative. The carbonitrile group lies almost in the plane of the attached planar pyridine ring system.

The crystal structure features a N3—H3···N2⁽ⁱ⁾ [symmetry code: (i) 2 - x, 2 - y, -z] hydrogen bonded R₂² (16) motif (Fig. 2). No significant π—π stacking interaction between neighboring aromatic rings or C—H···π interaction towards them are observed.

S2. Experimental

A mixture of 3-(1H-indol-3-yl)-3-oxopropanenitrile 1 (1 mmol), 4,4,4-trifluoro-1-phenylbutane-1,3-dione 2 (1 mmol) and 4-chloro benzaldehyde 3 (1 mmol) in the presence of ammonium acetate (400 mmol) under solvent-free condition was heated at 110 °C for 6 h. After completion of the reaction (TLC), the reaction mixture was poured into water and extracted with dichloromethane. After removal of the solvent, the residue was chromatographed over silica gel (230–400 mesh) using petroleum ether-ethyl acetate mixture (7:3 v/v), which afforded the pure compound. Melting point:273 °C, Yield: 70%.