Ethyl (Z)-2-cyano-3-(9-ethyl-9H-carbazol-3-yl)prop-2-enoate

Abdullah Mohamed Asiri; Mehmet Akkurt; Salman A Khan; Islam Ullah Khan; Muhammad N Arshad

doi:10.1107/S1600536809015505

. 2009 Apr 30;65(Pt 5):o1169. doi: 10.1107/S1600536809015505

Ethyl (Z)-2-cyano-3-(9-ethyl-9H-carbazol-3-yl)prop-2-enoate

Abdullah Mohamed Asiri ^a, Mehmet Akkurt ^b,^*, Salman A Khan ^a, Islam Ullah Khan ^c, Muhammad N Arshad ^c

PMCID: PMC2977834 PMID: 21583971

Abstract

In the title compound, C₂₀H₁₈N₂O₂, weak intermolecular C—H⋯O and C—H⋯N interactions generate a chain that runs parallel to the b axis and incorporates C(7) and R ₂ ²(15) graph-set motifs. The supramolecular aggregation is completed by the presence of weak C—H⋯π interactions.

Related literature

For background to the applications of carbazole derivatives, see: Park et al. (1998 ▶); Kimoto et al. (2004 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₀H₁₈N₂O₂
M _r = 318.36
Monoclinic,
a = 10.8030 (7) Å
b = 13.4443 (10) Å
c = 11.6160 (7) Å
β = 93.387 (5)°
V = 1684.15 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.35 × 0.10 × 0.05 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
19261 measured reflections
4195 independent reflections
1121 reflections with I > 2σ(I)
R _int = 0.146

Refinement

R[F ² > 2σ(F ²)] = 0.084
wR(F ²) = 0.228
S = 0.91
4195 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015505/hb2957sup1.cif

e-65-o1169-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015505/hb2957Isup2.hkl

e-65-o1169-Isup2.hkl^{(205.6KB, 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
C9—H9⋯O1ⁱ	0.93	2.58	3.255 (5)	130
C12—H12⋯N2ⁱⁱ	0.93	2.58	3.491 (6)	165
C17—H17B⋯Cg2ⁱⁱⁱ	0.97	2.82	3.692 (5)	150

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg2 is the centroid of the C7–C12 ring.

Acknowledgments

AMA acknowledges the Deanship of Scientific Research at KAU for grant No. 3–50/429.

supplementary crystallographic information

Comment

Nonlinear optical (NLO) andelectro-optic (EO) properties of organic dyes have been the hot subject nowadays because of the potential applications in optical switching, optical telecommunication devices, optical disks, new type of dye lasers (Kimoto et al., 2004). Carbazole derivatives have important roles of optical material due to their special photorefractive, electrical, and chemical properties. Carbazoles are well known as a conjugated, good hole transporting, electron-donor, planar compound and easy to introduce solubilizing groups to rigid ring structure (Park et al., 1998).

The molecular structure of title compound (I) is shown in Fig. 1. The bond lengths and angles in (I) display normal values (Allen et al., 1987). The nine-membered ring N1/C1—C8 is essentially planar, with maximum deviations of 0.014 (5)Åfor C5 and -0.025 (4) Å for C7 from its mean plane, respectively. In the molecule of (I), the rest atoms of the molecule lie close to the nine-membered ring plane, with the maximum deviations of 1.110 (7), -0.467 (3) and -0.341 (5) Å, for C20, O1 and C18, respectively.

The crystal structure of (I) is stabilized by weak C—H···O and C—H···N interactions (Table 1, Fig. 2), that generates a chain which runs parallel to the baxis and has the graph-set motifs of C(7) and R₂²(15). The supramolecular aggregation is completed by the presence of C—H···π interactions (Table 1).

Experimental

Equivalent molar quantities of N-ethyl carbazol-9-carboxaldehyde (1.0 g, 4.48 mmol) and ethylcyanoacetate (0.51 g, 4.48 mmol) were dissolved in 25 ml e thanol then heated at reflux. Pipyridine (one drop) was added to the solution and reflux was continued for 6 h. The solution was cooled to room temperature and the solid products were filtered and washed with ethanol (25 ml). Recrystalization from ethanol gave yellow prisms of (I). Yield: (0.4 g, 29%); m.p. 385 K; IR (KBr) ν_maxcm^-1. 3028 (C—H aromatic), 2978 (–C—H aliphatic), 2216 (CN), 1721(C=O), 1573 (C=C), 1225 (C—O), 1127 (C—N).). ¹H NMR(CDCl₃): δ 8.15 (H-1), 8.19 (H-2), 8.41(H-3), 7.45 (H-4), 7.33 (H-5), 7.54 (H-6), 7.45 (H-7), 8.74 (H-8), 4.39 (CH₃—CH₂—N), 1.41 (CH₃—CH₂—N), 4.39 (CH₃—CH₂—O), 1.41 (CH₃—CH₂—O).