Crystal structure of 4-(2-azido­phen­yl)-5-benzoyl-2-(1H-indol-3-yl)-1H-pyrrole-3-carbo­nitrile

G Vimala; J Kamal Raja; Y Amina Naaz; P T Preumal; A SubbiahPandi

doi:10.1107/S2056989015006921

. 2015 Apr 22;71(Pt 5):o335–o336. doi: 10.1107/S2056989015006921

Crystal structure of 4-(2-azidophenyl)-5-benzoyl-2-(1H-indol-3-yl)-1H-pyrrole-3-carbonitrile

G Vimala ^a, J Kamal Raja ^b, Y Amina Naaz ^a, P T Preumal ^b, A SubbiahPandi ^a,^*

PMCID: PMC4420135 PMID: 25995935

Abstract

In the title compound, C₂₆H₁₆N₆O, the dihedral angles between the central pyrrole ring and the pendant indole ring system (r.m.s. deviation = 0.027 Å) and the azide-bearing benzene ring are 37.56 (8) and 51.62 (11)°, respectively. The azide group is almost coplanar with its attached benzene ring [C—C—N—N = 3.8 (3)°]. The benzoyl benzene ring is disordered over two orientations twisted with respect to each other by 9.29 (8)° in a 0.514 (2):0.486 (2) ratio. In the crystal, inversion dimers linked by pairs of N_p—H⋯O (p = pyrrole) hydrogen bonds generate R ₂ ²(10) loops. A second inversion dimer arises from a pair of N_i—H⋯N_c (i = indole and c = cyanide) hydrogen bonds, which generates an R ₂ ²(16) loop. Together, the hydrogen bonds lead to [011] chains in the crystal.

Keywords: crystal structure, indole derivatives, pyrrole-3-carbonitrile, hydrogen bonding

Related literature

For background to indole derivatives, see: Srivastava, Anupam & Pandeya (2011 ▸). For related structures, see: Srinivasan et al. (2012 ▸); Inglebert et al. (2013 ▸). graphic file with name e-71-0o335-scheme1.jpg

Experimental

Crystal data

C₂₆H₁₆N₆O
M _r = 428.45
Triclinic,
a = 8.1834 (6) Å
b = 11.3713 (8) Å
c = 12.6853 (8) Å
α = 108.070 (3)°
β = 105.164 (4)°
γ = 90.256 (3)°
V = 1078.42 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.35 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T _min = 0.901, T _max = 0.987
20625 measured reflections
4315 independent reflections
3062 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.143
S = 1.04
4315 reflections
325 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.25 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 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015006921/hb7394sup1.cif

e-71-0o335-sup1.cif^{(25.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006921/hb7394Isup2.hkl

e-71-0o335-Isup2.hkl^{(211.4KB, hkl)}

Click here for additional data file.^{(7.9KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015006921/hb7394Isup3.cml

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

. DOI: 10.1107/S2056989015006921/hb7394fig1.tif

The molecular structure of the title compound, with displacement ellipsoids drawn at 30% probability level.

Click here for additional data file.^{(2MB, tif)}

c . DOI: 10.1107/S2056989015006921/hb7394fig2.tif

The crystal packing of the title compound viewed along c axis. Hydrogen atoms are omitted for clarity.

CCDC reference: 933255

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

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N2H2AO1ⁱ	0.92(1)	1.95(1)	2.8526(17)	166(2)
N1H1AN3ⁱⁱ	0.92(1)	2.10(1)	2.988(2)	163(2)

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

Acknowledgments

GV and ASP thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray data collection.

supplementary crystallographic information

S1. Experimental

To a stirred mixture of 2-azido aldehydes 1 (1.0 mmol), 2- (1H-3-indolylcarbonyl)-3-aryl-2-propenenitriles 2 (1.0 mmol) and phenacylazides 3 (1.0 mmol) in water (3 ml) piperidine (0.25 mmol) was added at 80 ⁰ C. The turbid solution slowly turned into a clear solution followed by the formation of solid with 0.75 min. After completion of the reaction as indicated by thin layer chromatography (TLC), the solid was filtered and washed with pet-ether: EtOAc mixture (1: 1 ratio v/v, 5 ml) to give pure compounds. The compound was recrystallized from methanol to yield yellow crystals. The yield of the isolated product was 91%. Yellow blocks were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.