1-[9-Ethyl-6-(2-methyl­benzo­yl)-9H-carbazol-3-yl]ethanone

Ye-Chao Hang; Jin-Xiu Ji; Min-Dong Chen

doi:10.1107/S1600536809016080

. 2009 May 7;65(Pt 6):o1198. doi: 10.1107/S1600536809016080

1-[9-Ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone

Ye-Chao Hang ^a,^*, Jin-Xiu Ji ^b, Min-Dong Chen ^a

PMCID: PMC2969787 PMID: 21583069

Abstract

In the title compound, C₂₄H₂₁NO₂, the pendant benzene ring is inclined at a dihedral angle of 86.66 (18)° with respect to the adjacent aromatic ring of the carbozole unit. In the crystal structure, symmetry-related molecules are linked via C—H⋯O and C—H⋯π interactions.

Related literature

For carbazole-containing compounds used as organic opto-electronic materials, see: Bai et al. (2007 ▶); Liu et al. (2009 ▶); Promarak et al. (2007 ▶). For the synthesis, see: Feng et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₄H₂₁NO₂
M _r = 355.42
Orthorhombic,
a = 13.066 (3) Å
b = 13.416 (3) Å
c = 21.987 (4) Å
V = 3854.2 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.977, T _max = 0.992
3492 measured reflections
3492 independent reflections
1733 reflections with I > 2σ(I)
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.178
S = 1.06
3492 reflections
244 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016080/su2106sup1.cif

e-65-o1198-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016080/su2106Isup2.hkl

e-65-o1198-Isup2.hkl^{(171.3KB, 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
C11—H11A⋯O1ⁱ	0.93	2.57	3.447 (5)	157
C16—H16A⋯O1ⁱ	0.97	2.54	3.476 (5)	163
C3—H3A⋯CgBⁱⁱ	0.93	2.78	3.671 (5)	161

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Symmetry codes: (i) Inline graphic ; (ii) . CgB is the centroid of the C9–C14 ring.

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

The title compound is an important intermediate in the synthesis of carbazole-containing compounds used as organic optoelectronic materials, which have large π—π conjugated networks (Bai et al. 2007; Promarak et al. 2007; Liu et al. 2009). Our interest in this field of research lead us to synthesize, and to report here on the crystal structure of the title compound.

The molecular structure of the title compound is illustrated in Fig. 1. The geometrical parameters are within normal ranges (Allen et al., 1987). The carbozole moiety is slighty bowed with ring B (C9—C14) being inclined to ring D (C17—C22) by 3.04 (19)°. The central ring C (N1,C12,C13,C17,C22) is inclined to rings B and D by 2.76 (18) and 0.30 (18)°, respectively. Ring A (C2—C7) is inclined to ring B by 86.66 (18)°.

In the crystal structure symmetry related molecules are linked via C—H···O and C—H···π interactions (Table 1 and Fig. 2).

Experimental

The title compound was prepared by a slight modification of a method reported in the literature (Feng et al., 2007). That is, the title compound was recrystalized from a mixture of methanol and dichloromethane (V/V = 2:1). On solw evaporation of the solvent colourless block-like crystals appeared after ca 4 days.