N-[(E)-(9-Ethyl-9H-carbazol-3-yl)methyl­idene]aniline

Nuray Yeksan; Ece Uzkara; Orhan Zeybek; Erol Asker

doi:10.1107/S1600536810018660

. 2010 May 26;66(Pt 6):o1456. doi: 10.1107/S1600536810018660

N-[(E)-(9-Ethyl-9H-carbazol-3-yl)methylidene]aniline

Nuray Yeksan ^a, Ece Uzkara ^a, Orhan Zeybek ^a, Erol Asker ^b,^*

PMCID: PMC2979658 PMID: 21579525

Abstract

The title compound, C₂₁H₁₈N₂, was obtained as the product of the reaction between 9-ethyl-9H-carbazole-3-carbaldehyde and aniline in ethanol. The crystal packing is stabilized mainly by C—H⋯π interactions between the carbazole benzene rings and the methylene H atoms.

Related literature

For background to photoconductive properties see: Segura (1998 ▶); Grigoras & Antonoaia (2005 ▶). For geometrical parameters in related structures, see: Wang et al. (2008 ▶); Huang et al. (2008 ▶).

Experimental

Crystal data

C₂₁H₁₈N₂
M _r = 298.37
Monoclinic,
a = 15.3350 (3) Å
b = 5.9692 (10) Å
c = 17.5447 (3) Å
β = 91.162 (1)°
V = 1605.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 K
0.6 × 0.4 × 0.2 mm

Data collection

Rigaku R-AXIS RAPID S diffractometer
28963 measured reflections
2838 independent reflections
2821 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.148
S = 1.41
2838 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: CrystalStructure (Rigaku & Rigaku/MSC, 2003 ▶); cell refinement: CrystalStructure; data reduction: SORTAV (Blessing, 1995 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810018660/om2337sup1.cif

e-66-o1456-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018660/om2337Isup2.hkl

e-66-o1456-Isup2.hkl^{(136.5KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the C1–C4/C4A/C9A and C4B/C5–C8/C8A rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg1ⁱ	0.93	2.87	3.587 (3)	135
C12—H12⋯Cg2ⁱ	0.93	2.98	3.660 (3)	131
C10—H10A⋯Cg2ⁱⁱ	0.97	3.25	4.050 (4)	142

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

Acknowledgments

The authors thank the Scientific Research Projects Department (BAP) at Balikesir University for financial support (Project No. 08/06).

supplementary crystallographic information

Comment

The structure of the title compound is depicted in (Fig. 1). The bond lengths and internal bond angles of the carbazole skeleton are comparable to those of related molecules (Wang et al., 2008; Huang et al., 2008). The carbazole and phenyl skeletons are essentially planar with r.m.s deviations of 0.021Å (carbazole ring) and 0.008Å (phenyl ring). The phenyl ring is twisted away from the carbazole ring by 67.45 (05)°. The ethyl group protrudes out of the plane of the carbazole skeleton as indicated by the C9A—N9—C10—C11 torsion angle of 86.0 (3)°. The only force that stack the molecules appears to be π-ring C—H···Cg intermolecular interactions among the benzene rings of carbazole and the hydrogen atoms H5, H10A and H12 (Fig. 2).

Experimental

The title compound was synthesized via the imine reaction between aniline and 9-ethyl-9H-carbazol-3-carbaldehyde in ethanol. In a round bottom flask fitted with a magnetic stirrer a solution was prepared from 9-ethyl-9H-carbazol-3-carbaldehyde (1.116 g, 5 mmol) and aniline (0.70 g, 7.5 mmol) in 50 ml ethanol at ambient temperature. After stirring for 2 h, the solution was left for crystallization overnight, after which time the product was precipitated as yellow crystals. The crude product was separated by filtration and washed with ethanol. Yellow, transparent crystals suitable for the X-ray diffraction analysis were grown from tetrahydrofuran by slow evaporation technique at ambient temperature, mp. 407 K. FT—IR (KBr) ν_max (cm^-1): 3048 (Ar—H), 2973 (-CH₃), 2930 (-CH₂-), 1618 (C=N), 1587, 1567 (Ar—N), 1489, 1473, 1461 (Ar C=C); ¹HNMR (300 MHz, CDCl₃, ppm): 1.46 (t, J = 7.3 Hz, 3H, CH₃), 4.38 (q, J = 7.3 Hz, 2H, -CH₂-), 7.21-7.59 (m, 9H, ArH), 8.07 (dd, J = 8.5 and 1.8 Hz, 1H, H2), 8.18 (dt, J = 7.9 and 0.8 Hz, 1H, H5), 8.64 (s, 1H, H12), 8.65 (d, J= 1.8, 1H, H4). UV-Vis, [EtOH, λmax (nm), (ε)] = 238 (25800), 293 (22100), 338 (18500).