1,4-Dibut­oxy-2,5-bis­{(Z)-2-[4-(9H-carbazol-9-yl)phen­yl]ethen­yl}benzene

Wen-Wen Fei; Rui Li; Zhen-Yu Wang; Jie-Ying Wu

doi:10.1107/S1600536812000414

. 2012 Jan 11;68(Pt 2):o321. doi: 10.1107/S1600536812000414

1,4-Dibutoxy-2,5-bis{(Z)-2-[4-(9H-carbazol-9-yl)phenyl]ethenyl}benzene

Wen-Wen Fei ^a, Rui Li ^a, Zhen-Yu Wang ^a, Jie-Ying Wu ^a,^*

PMCID: PMC3275010 PMID: 22346955

Abstract

The title compound, C₅₄H₄₈N₂O₂, lies about an inversion centre. The carbazole ring system makes dihedral angles of 58.43 (7) and 88.96 (7)°, respectively, with the adjacent and central benzene rings. The dihedral angle between the two benzene rings is 52.01 (8)°. In the crystal, molecules are linked by pairs of C—H⋯O interactions, forming a tape along the a axis. The methyl group is disordered over two sets of sites with occupancies of 0.63 (3) and 0.37 (3).

Related literature

For the crystal structures of related carbazole derivatives, see: Liu et al. (2007 ▶); Piotr (2011 ▶); Paital et al. (2007 ▶); Zhang et al. (2010 ▶). For applications of carbazole derivatives, see: Ravindranath (2007 ▶); Sun et al. (2011 ▶); Zhao et al. (2008 ▶).

Experimental

Crystal data

C₅₄H₄₈N₂O₂
M _r = 756.94
Monoclinic,
a = 8.437 (5) Å
b = 13.229 (5) Å
c = 19.165 (5) Å
β = 98.683 (5)°
V = 2114.5 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.979, T _max = 0.986
8735 measured reflections
3713 independent reflections
2969 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.153
S = 1.03
3713 reflections
274 parameters
32 restraints
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536812000414/is5035sup1.cif

e-68-0o321-sup1.cif^{(23.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000414/is5035Isup2.hkl

e-68-0o321-Isup2.hkl^{(178.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812000414/is5035Isup3.cml

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
C24—H24B⋯O1ⁱ	0.97	2.52	3.309 (4)	138

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant No. 21071001), the Education Committee of Anhui Province (grant No. KJ2010A030) and the Graduate Students Academic Innovation Research Project of Anhui University (grant No. yqh090020).

supplementary crystallographic information

Comment

Recently, carbazole-based materials have been investigated for their high electrical and nonlinear optical properties (Ravindranath et al., 2007; Sun et al., 2011; Zhao et al., 2008). The introduction about the structure of carbazole derivatives has been reported (Paital et al., 2007; Piotr et al., 2011). In the title molecule (Fig. 1), which is centrosymmetric, there are two 9-phenyl-9H-carbazole rings and a central benzene ring. In the crystal structure, the neighboring molecules are connected through weak intermolecular C—H···O interactions.

Experimental

4-(9H-Carbazol-9-yl)benzaldehyde (0.30 g, 1.1 mmol), 2,5-dibutoxy-1,4-bis(triphenylphosphonium)benzene dichloride (0.42 g, 0. 5 mmol) and tert-BuOK (0.34 g, 3 mmol) were added to a mortar with grinding fully. The reaction residue was extracted with 200 ml of dichloromethane, washed four times with distilled water, and dried with anhydrous MgSO₄. Then it was filtered and concentrated, purified by flash column-chromatography on silica. Elution with petroleum/ethyl acetate (50:1) gave the yellow powders (yield 69%).