3-[2-(9-Ethyl-9H-carbazol-3-yl)-6-methyl-3-quinol­yl]propan-1-ol

S Murugavel; S Ranjith; A SubbiahPandi; G Periyasami; R Raghunathan

doi:10.1107/S1600536808042153

. 2008 Dec 17;65(Pt 1):o139–o140. doi: 10.1107/S1600536808042153

3-[2-(9-Ethyl-9H-carbazol-3-yl)-6-methyl-3-quinolyl]propan-1-ol

S Murugavel ^a, S Ranjith ^b, A SubbiahPandi ^b,^*, G Periyasami ^c, R Raghunathan ^c

PMCID: PMC2968056 PMID: 21581598

Abstract

In the title compound, C₂₇H₂₆N₂O, the mean planes through the carbazole and quinoline ring systems form a dihedral angle of 67.23 (5)°. Molecules are linked into cyclic centrosymmetric dimers by O—H⋯N hydrogen bonds, and C—H⋯π interactions with the pyridine ring of the quinoline ring system as an acceptor. The dimers are linked through C—H⋯O hydrogen bonds.

Related literature

For the biological activity and applications of carbazole derivatives, see: Itoigawa et al. (2000 ▶); Tachibana et al. (2001 ▶); Ramsewak et al. (1999 ▶); Friend et al. (1999 ▶); Diaz et al. (2002 ▶); Zhang et al. (2004 ▶). For the biological properties of quinoline derivatives, see: Cunico et al. (2006 ▶); Hartline et al. (2005 ▶). For related structures, see: Murugavel et al. (2008 ▶); Chakkaravarthi et al. (2008 ▶).

Experimental

Crystal data

C₂₇H₂₆N₂O
M _r = 394.50
Monoclinic,
a = 13.6417 (5) Å
b = 9.8599 (3) Å
c = 16.3208 (5) Å
β = 109.658 (2)°
V = 2067.30 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.21 × 0.19 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.984, T _max = 0.987
27360 measured reflections
6459 independent reflections
3912 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.228
S = 1.02
6459 reflections
316 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.39 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 and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042153/ci2733sup1.cif

e-65-0o139-sup1.cif^{(23.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042153/ci2733Isup2.hkl

e-65-0o139-Isup2.hkl^{(309.8KB, 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—H1⋯N2ⁱ	0.82	2.18	2.987 (2)	166
C17—H17⋯O1ⁱⁱ	0.97 (2)	2.38 (2)	3.334 (3)	171 (2)
C10—H10⋯Cg1ⁱ	0.96 (3)	2.76 (2)	3.559 (2)	141 (2)

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the centroid of the N2/C15–C19 ring.

Acknowledgments

SM and ASP thank Dr Babu Varghese, SAIF, IIT, Madras, India, for his help with the data collection.

supplementary crystallographic information

Comment

Carbazole and its derivatives have become quite attractive compounds owing to their applications in pharmacy and molecular electronics. It has been reported that carbazole derivatives possess various biological activities, such as antitumor (Itoigawa et al., 2000), antioxidative (Tachibana et al., 2001), anti-inflammatory and antimutagenic (Ramsewak et al., 1999) activities. Carbazole derivatives also exhibit electroactivity and luminescence properties and are considered to be potential candidates for electronics such as colour displays, organic semiconductor lasers and solar cells (Friend et al., 1999). These compounds are thermally and photochemically stable, which makes them useful materials for technological applications. For instance, the carbazole ring is easily funtionalized and covalently linked to other molecules (Diaz et al., 2002). This enables its use as a convenient building block for the design and synthesis of molecular glasses, which are widely studied as components of electroactive and photoactive materials (Zhang et al., 2004). Quinoline derivatives are known to possess a variety of biological properties such as antimalarial and antiviral activity (Cunico et al., 2006; Hartline et al., 2005). Against this background, and in order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound was carried out.

The carbazole and quinoline ring systems are individually planar, with maximum deviations of 0.077 (1) and 0.034 (2) Å for atoms C9 and C22, respectively. The sum of the bond angles around N1 (351.7°) of the pyrrole ring is in accordance with sp² hybridization. The N1—C1 [1.372 (3) Å] and N1—C12 [1.382 (2) Å] bond lengths are normal and are comparable with the corresponding values observed in a related structure (Chakkaravarthi et al., 2008; Murugavel et al., 2008). The mean planes through the carbazole and quinoline ring systems form a dihedral angle of 67.23 (5)°.

The molecules at (x, y, z) and (1-x, 2-y, 1-z) are linked by O1—H1···N2 hydrogen bonds into a cyclic centrosymmetric R₂²(16) dimer (Fig. 2). Within the dimer, C10–H10···π interactions with the pyridine ring of the quinoline ring system as an acceptor are observed. Atom C17 in the molecule (x, y, z) donate one proton to atom O1 of the molecule at (1 - x, -1/2 + y, 3/2 - z) forming a C(7) chain along the [010].

Experimental

InCl₃ (20 mol%) was added to a mixture of 3,4-dihydro-2H-pyran (1 mmol) and N-[(9-Ethyl-9H-carbazol-6-yl)methylene]-4-methylbenzenamine (1 mmol) in dry acetonitrile (10 ml) and the reaction mixture was refluxed until the completion of the reaction as indicated by TLC. The reaction mixture was then quenched with water, extracted with excess of ethyl acetate. The organic layer was washed with water and dried over anhydrous MgSO₄. The solvent was evaporated in vacuo and the crude product was chromatographed on silica gel (ethylacetate-hexane, 2:8) to afford quinoline propanol. The pure compound was crystallized from ethylacetate-hexane 1:9). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a ethylacetate solution at room temperature.