9-(4-Bromo­phen­yl)-3,6-di-tert-butyl-9H-carbazole

Jing-Ya Zhang; Wei-Yi Zhang

doi:10.1107/S1600536811047386

. 2011 Nov 16;67(Pt 12):o3307. doi: 10.1107/S1600536811047386

9-(4-Bromophenyl)-3,6-di-tert-butyl-9H-carbazole

Jing-Ya Zhang ^a,^*, Wei-Yi Zhang ^b

PMCID: PMC3238959 PMID: 22199808

Abstract

The asymmetric unit of the title compound, C₂₆H₂₈BrN, contains two independent molecules in which the carbazole rings are almost planar, with r.m.s. deviations of 0.0212 (1) and 0.0229 (1) Å. The dihedral angles between the carbazole ring system and the pendent benzene ring are 60.5 (1) and 56.3 (1)° in the two molecules. In the crystal, molecules are linked into chains along the b axis by C—H⋯π interactions.

Related literature

For background to the applications of the title compound, see: Wang et al. (2008 ▶). For the synthesis of the title compound, see: Weber et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₆H₂₈BrN
M _r = 434.40
Triclinic,
a = 5.9300 (12) Å
b = 17.634 (4) Å
c = 22.343 (5) Å
α = 100.38 (3)°
β = 95.13 (3)°
γ = 99.32 (3)°
V = 2250.8 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.84 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.710, T _max = 0.838
9130 measured reflections
8267 independent reflections
3724 reflections with I > 2σ(I)
R _int = 0.054
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.076
wR(F ²) = 0.160
S = 1.00
8267 reflections
505 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.54 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 datablock(s) I, global. DOI: 10.1107/S1600536811047386/vm2131sup1.cif

e-67-o3307-sup1.cif^{(34.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047386/vm2131Isup2.hkl

e-67-o3307-Isup2.hkl^{(404.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811047386/vm2131Isup3.cml

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

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

Cg3, Cg11 and Cg8 are the centroids of the C7–C12, C47–C52 and N2/C27/C32–C34 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22A⋯Cg3ⁱ	0.93	2.75	3.544 (8)	144
C25—H25A⋯Cg11ⁱⁱ	0.93	2.92	3.511 (7)	123
C52—H52A⋯Cg8ⁱⁱⁱ	0.93	2.95	3.591 (8)	127

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

Acknowledgments

This work was supported by the Fund of Henan Chinese Medicine (BSJJ2009–29). The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

supplementary crystallographic information

Comment

The title compound, 9-(4-bromophenyl)-3,6-di-tert-butyl-9H-carbazole, is an important intermediate, which can be utilized to synthesize organic semiconductors and conjugated polymers (Wang et al. , 2008). Here we report here its crystal structure (Fig. 1).

The two molecules in the asymmetric unit have the same conformation (r.m.s. deviation 0.2092 Å for all non-H atoms fitted) . The bond lengths and angles are within normal ranges (Allen et al., 1987). The carbazole rings are almost planar. The dihedral angles of the rings A(C1—C6/N1/C7—C12), B(C21—C26), C(C27—C32/N2/C33—C38), D(C47—C52) are: A/B = 60.5 (1)°, C/D = 56.3 (1)°.

In the crystal packing, there are not classic hydrogen bonds found. The molecular chains are linked by C—H···π interactions (Table 1) to give a three-dimensional network, which seems to be very effective in the stabilization of the crystal structure.

Experimental

The title compound, (I) was prepared by a method reported in literature (Weber et al. , 2011). The crystals were obtained by dissolving (I) (0.5 g) in methanol (50 ml) and evaporating the solvent slowly at room temperature for about 10 d.