9-p-Tolyl-9H-carbazole-3-carbonitrile

C Ramathilagam; N Venkatesan; P Rajakumar; P R Umarani; V Manivannan

doi:10.1107/S1600536811039286

. 2011 Sep 30;67(Pt 10):o2796. doi: 10.1107/S1600536811039286

9-p-Tolyl-9H-carbazole-3-carbonitrile

C Ramathilagam ^a, N Venkatesan ^b, P Rajakumar ^b, P R Umarani ^c, V Manivannan ^d,^*

PMCID: PMC3201498 PMID: 22058824

Abstract

In the title compound, C₂₀H₁₄N₂, the carbazole ring system is essentially planar (r.m.s. deviation = 0.187 Å) and is inclined at an angle of 54.33 (4) ° with respect to the benzene ring. The crystal packing is stabilized by weak C—H⋯N and C—H⋯π interactions.

Related literature

For the biological activity of carbazole derivatives, see: Ramsewak et al. (1999 ▶); Tachibana et al. (2001 ▶); Itoigawa et al. (2000 ▶). For related structures, see: Archana et al. (2010 ▶); Velmurugan et al. (2010 ▶); Yuan et al. (2010 ▶).

Experimental

Crystal data

C₂₀H₁₄N₂
M _r = 282.33
Triclinic,
a = 8.6031 (3) Å
b = 8.8247 (3) Å
c = 10.4609 (4) Å
α = 80.514 (2)°
β = 87.499 (2)°
γ = 72.114 (2)°
V = 745.45 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.22 × 0.19 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.984, T _max = 0.987
13631 measured reflections
3724 independent reflections
2695 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.123
S = 1.04
3724 reflections
200 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.21 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/S1600536811039286/pv2449sup1.cif

e-67-o2796-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039286/pv2449Isup2.hkl

e-67-o2796-Isup2.hkl^{(178.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039286/pv2449Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯N2ⁱ	0.93	2.57	3.434 (2)	154
C15—H15⋯Cg2ⁱⁱ	0.93	2.71	3.453 (1)	137

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

Acknowledgments

CR wishes to acknowledge AMET University management, India, for their kind support.

supplementary crystallographic information

Comment

Carbazole derivatives possess antioxidative (Tachibana et al., 2001), antitumor (Itoigawa et al., 2000), anti-inflammatory and antimutagenic (Ramsewak et al., 1999) activities.

The geometric parameters of the title molecule (Fig. 1) agree well with the corresponding geometric parameters reported in similar structures (Archana et al., 2010; Velmurugan et al., 2010; Yuan et al., 2010). The carbazole ring system is essentially planar with maximum deviation of C9 from the least-squae plane defined by the atoms N1/C1–C12 being 0.0306 (10) Å. The mean plane of the carbazole ring system makes a dihedral angle of 54.33 (4) ° with the phenyl ring. The sum of bond angles around N1 [359.87 (10) °]indicates the sp² hybridization state of atom N1 in the molecule. The crystal packing of the compound is stabilized by weak C8—H8···N2 hydrogen bonds and C15—H15···π interactions involving the centroid of C1–C6 ring (Table 1).

Experimental

To a stirred solution of AlCl₃ (2.8 g, 2.1 mmol), in dry THF (100 ml) sodium azide (4.1 g, 6.31 mmol), and 9-p-tolyl-9H-carbazole-3-carbaldehyde (3 g, 1.05 mmol) were added and the resulting mixture was heated to gentle reflux. The progress of the reaction was monitored by TLC. The suspension gradually turned pale yellow after 5–6 h. Then excess THF was removed by distillation and the residue was diluted with 10% HCl (10 ml). The aqueous layer was extracted with CHCl₃ (2x50 ml) and brine (25 ml). The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography by elution with mixture of ethyl acetate and hexane (1:4) to give the title compound as colorless crystalline solid.(m.p 449 K).