(Z)-9-(1,2-Dichloro­vin­yl)-9H-carbazole

Miho Ukai; Hideyuki Tabata; Tsunehisa Okuno

doi:10.1107/S1600536813007137

. 2013 Mar 20;69(Pt 4):o555. doi: 10.1107/S1600536813007137

(Z)-9-(1,2-Dichlorovinyl)-9H-carbazole

Miho Ukai ^a, Hideyuki Tabata ^a, Tsunehisa Okuno ^a,^*

PMCID: PMC3629607 PMID: 23634094

Abstract

There are two independent molecules in the asymmetric unit of the title compound, C₁₄H₉Cl₂N, in which the dihedral angles between the dichlorovinyl unit (r.m.s. deviations = 0.0003 and 0.0009 Å), and the carbazole ring are 87.77 (3) and 72.90 (3)°.

Related literature

For the preparation of the title compound, see: Okamoto & Kundu (1970 ▶); Cuniberti et al. (1996 ▶). For the structure of 9-vinylcarbazole, see: Tsutsui et al. (1976 ▶); Tian et al. (2006 ▶). For the optoelectric properties of vinylcarbazoles, see: Ye et al. (2010 ▶).

Experimental

Crystal data

C₁₄H₉Cl₂N
M _r = 262.14
Monoclinic,
a = 6.6552 (7) Å
b = 24.872 (3) Å
c = 14.8636 (15) Å
β = 93.7529 (16)°
V = 2455.1 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 93 K
0.14 × 0.11 × 0.07 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: numerical (NUMABS; Rigaku, 1999 ▶) T _min = 0.939, T _max = 0.965
19841 measured reflections
5595 independent reflections
5154 reflections with F ² > 2σ(F ²)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.092
S = 1.04
5594 reflections
323 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 forWindows (Farrugia, 2012 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(32.5KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007137/qm2093sup1.cif

e-69-0o555-sup1.cif^{(32.5KB, cif)}

Click here for additional data file.^{(273.9KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007137/qm2093Isup2.hkl

e-69-0o555-Isup2.hkl^{(273.9KB, hkl)}

Click here for additional data file.^{(4.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813007137/qm2093Isup3.cml

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

Acknowledgments

This work was supported by the Adaptable and Seamless Technology Transfer Program through Target-driven R&D from the Japan Science and Technology Agency (JST).

supplementary crystallographic information

Comment

Vinylcarbazoles are interesting as monomers of poly(N-vinylcarbazoles) which have been attracted interest from the viewpoint of their optoelectric properties (Ye et al., 2010). The title compound, C₁₄H₉N₁Cl₂, is a halogen analogue of vinylcarbazole. In the literature (Okamoto & Kundu, 1970), the compoud is a mixture of E and Z forms. The crystals, however, were found to have only a Z form.

There are two independent molecules (A and B) in the asymmetric unit (Fig. 1). The carbazole rings are planar (N1/C1—C12 plane: r.m.s. deviation = 0.0194 Å, N2/C15—C26 plane: r.m.s. deviation = 0.0377 Å). The dichlorovinyl parts are also planar (Cl1/Cl2/C13/C14 plane: r.m.s. deviation = 0.0009 Å, Cl3/Cl4/C27/C28 plane: r.m.s. deviation = 0.0003 Å). The dihedral angles between the dichlorovinyl part and the carbazole ring are 87.77 (3)° for A and 72.90 (3)° for B, which are larger than those in vinylcarbazole (Tsutsui et al., 1976 and Tian et al., 2006), suggesting steric repulsion of the Cl1 or Cl3 with the hydrogen atoms of the carbazole rings. The inter-molecular contacts are dominated by C-H···π interactions which involve both six-membered rings of both molecules A and B (Fig. 2).

Experimental

The title compound was prepared according to a published procedure (Cuniberti et al., 1996). The single crystals with sufficient quality for X-ray analysis were grown slowly from the oilish mixture.