(E)-3-(9-Hexyl-9H-carbazol-3-yl)acrylic acid

Wan Sun; Wen-Mo Liu; Sheng-Li Li

doi:10.1107/S1600536814016237

. 2014 Jul 31;70(Pt 8):o884. doi: 10.1107/S1600536814016237

(E)-3-(9-Hexyl-9H-carbazol-3-yl)acrylic acid

Wan Sun ^a,^b, Wen-Mo Liu ^a,^b, Sheng-Li Li ^a,^b,^*

PMCID: PMC4158515 PMID: 25249926

Abstract

In the title compound, C₂₁H₂₃NO₂, the hexyl group adopts an extended conformation, the six C atoms are nearly coplanar [maximum deviation = 0.082 (3) Å] and their mean plane is approximately perpendicular to the carbazole ring system, with a dihedral angle of 78.91 (15)°. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming inversion dimers; π–π stacking between carbazole ring systems of adjacent dimers further links the dimers into supramolecular chains propagating along the b-axis direction [centroid-to-centroid distances = 3.868 (2) and 3.929 (2) Å].

Keywords: crystal structure

Related literature

For structures of related carbazole derivatives, see: Saeed et al. (2010 ▶). For applications of carbazole derivatives, see: Adhikari et al. (2009 ▶); Daicho et al. (2013 ▶); Tao et al. (2010 ▶); Zheng et al. (2012 ▶); Dvornikov et al. (2009 ▶).

Experimental

Crystal data

C₂₁H₂₃NO₂
M _r = 321.40
Monoclinic,
a = 10.594 (5) Å
b = 5.109 (2) Å
c = 33.152 (15) Å
β = 94.922 (6)°
V = 1787.5 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
11882 measured reflections
3115 independent reflections
2291 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.192
S = 1.07
3115 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S1600536814016237/xu5796sup1.cif

e-70-0o884-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016237/xu5796Isup2.hkl

e-70-0o884-Isup2.hkl^{(152.9KB, hkl)}

Click here for additional data file.^{(6.8KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814016237/xu5796Isup3.cml

CCDC reference: 992361

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.85	2.650 (3)	166

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by Anhui Provincial Natural Science Foundation (grant No. 1308085MB24) and the Foundation of Educational Commission of Anhui Province, China (grant No. KJ2012A025).

supplementary crystallographic information

S1. Comment

Recently, carbazole derivatives have attracted attention as their superphotoelectric effect (Tao et al., 2010) and electron transporting capabilities (Zheng et al., 2012). So they have been widely used in biochemistry optical switching (Adhikari et al., 2009), 3-D microfabrication (Daicho et al., 2013) and optical data storage (Dvornikov et al., 2009). In the present paper, the title carbazole derivative (Fig.1) is synthesized.

In the molecule, the carbazole and carboxylic acid are coplanar, while the hexyl group is nearly perpendicular to the plan of carbazole ring [dihedral angle = 78.91 (15)°]. The molecule connect with each other by intermolecular hydrogen-bonding O1—H1···O2.

S2. Experimental

Carbazole single aldehyde (1.6 g, 5 mmol) and malonic acid (1.04 g, 10 mmol) was dissolved in pyridine with addition of 0.1 ml piperidine. The mixture was refluxed for 3 h, traced by TLC then column chromatography (silica, petroleum ether: ethyl acetate (V/V) = 5: 1) and finally 1.2 g white solid were acquired. Yield: 37%. 0.1 g LCOOH was dissolved in 30 ml me thanol, filtered to 50 ml volumetric flask, naturally evaporated for a week, and then colorless single crystals were obtained. ¹H NMR (400 MHz, CD₃COCD₃) 0.84 (t, 3H), 1.33 (m, 6H), 1.89 (m, 2H), 4.46 (t, 2H), 6.59 (d, 1H), 7.26 (t, 1H), 7.50 (t, 1H), 7.62 (t, 2H), 7.82 (d, 1H), 7.87 (d, 1H), 8.23 (t, 1H), 8.51 (s, 1H), 10.53 (s, 1H).