3-(9H-Carbazol-9-yl)propan-1-ol

N Haridharan; V Ramkumar; R Dhamodharan

doi:10.1107/S1600536810051809

. 2010 Dec 18;67(Pt 1):o180. doi: 10.1107/S1600536810051809

3-(9H-Carbazol-9-yl)propan-1-ol

N Haridharan ^a, V Ramkumar ^a, R Dhamodharan ^a,^*

PMCID: PMC3050424 PMID: 21522686

Abstract

In the title compound, C₁₅H₁₅NO, the dihedral angle between the benzene rings is 2.25 (2)°. The C—C—C—O atoms of the propanol side chain are in a gauche conformation [torsion angle = −60.5 (2)°]. In the crystal, O—H⋯O hydrogen bonds link the molecules into C(2) chains propagating in [100]. The O-bonded H atom is disordered over two sites of equal occupancy.

Related literature

For applications of the title compound, see: Chakkaravarthi et al. (2008 ▶); Murugavel et al. (2009 ▶). For related structures, see: Chen et al. (2009 ▶); Uludağ et al. (2010 ▶)

Experimental

Crystal data

C₁₅H₁₅NO
M _r = 225.28
Monoclinic,
a = 5.2930 (6) Å
b = 12.5935 (16) Å
c = 17.954 (2) Å
β = 97.778 (6)°
V = 1185.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.32 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.975, T _max = 0.986
8147 measured reflections
2721 independent reflections
1566 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.142
S = 0.97
2721 reflections
162 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051809/hb5760sup1.cif

e-67-0o180-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051809/hb5760Isup2.hkl

e-67-0o180-Isup2.hkl^{(133.6KB, 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
O1—H1O⋯O1ⁱ	0.95 (2)	1.91 (3)	2.834 (3)	163 (6)
O1—H1OA⋯O1ⁱⁱ	0.89 (6)	1.96 (6)	2.850 (4)	172 (6)

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

Acknowledgments

The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.

supplementary crystallographic information

Comment

The title compound, C₁₅H₁₅NO, (I) is a carbazole based alcohol derivative. It has a tricyclic structure, consisting of two six-membered benzene ring fused on either side of a five-membered nitrogen-containing ring (Uludağ et al. 2010; Chen et al. 2009). A propan-1-ol group is linked to the nitrogen atom of the carbazole.

It is an important heterocyclic aromatic compound in which the alcohol group is used as a linker for the preparation of various carbazole derivatives (Murugavel et al. 2009; Chakkaravarthi et al. 2008). The tricyclic structure is essentially planar, making a dihedral angle of 2.25 (2)° with the two outer most aromatic rings. The crystal packing is stabilized by a bifurcated O—H···O interaction linking the molecules into chains along the a axis.

Experimental

Carbazole (5 g, 0.03 moles), sodium hydride (2.88 g, 0.12 moles) and dry THF (400 ml) were placed in a 3-neck round bottomed flask equipped with a magnetic stirrer. The flask was purged with dry N₂ gas, sealed and placed in a salt ice-bath (-15 °C). The reaction mixture was allowed to stir for 1 h. 3-bromo-1-propanol (4 g, 0.03 mole), was then added slowly to the reaction mixture through a syringe. The reaction was allowed to continue for a period of 12 h, at ambient temperature. The product obtained was isolated by quenching the excess sodium hydride and the solvent was evaporated. The final product was dissolved in ethyl acetate, rinsed with water and dried with anhydrous MgSO₄. The product was purified by column chromatography technique using 10% ethyl acetate in hexane as the eluent to obtain pure bright white crystals. Recrystallization of the compound from chloroform gave colourless blocks of (I).