(2-Chloro­benzo[h]quinolin-3-yl)methanol

F Nawaz Khan; S Mohana Roopan; Venkatesha R Hathwar; R Rajesh; M Khawar Rauf

doi:10.1107/S1600536810010767

. 2010 Mar 27;66(Pt 4):o953. doi: 10.1107/S1600536810010767

(2-Chlorobenzo[h]quinolin-3-yl)methanol

F Nawaz Khan ^a, S Mohana Roopan ^a, Venkatesha R Hathwar ^b, R Rajesh ^c, M Khawar Rauf ^d,^*

PMCID: PMC2983997 PMID: 21580757

Abstract

In the title molecule, C₁₄H₁₀ClNO, all non-H atoms are coplanar (r.m.s deviation = 0.0266 Å). In the crystal, symmetry-related molecules are hydrogen bonded via intermolecular O—H⋯O interactions, forming chains along the b axis.

Related literature

The title compound was obtained by the reduction of an aldehyde using Montmorillonite K-10 as catalyst. For background to the use of Montmorillonite clays as catalysts, see: Roopan et al. (2009b ▶). For related structures, see: Khan et al. (2010a ▶,b ▶); Roopan et al. (2009a ▶).

Experimental

Crystal data

C₁₄H₁₀ClNO
M _r = 243.68
Monoclinic,
a = 16.6953 (4) Å
b = 4.61459 (11) Å
c = 14.5588 (3) Å
β = 95.123 (2)°
V = 1117.16 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 295 K
0.35 × 0.30 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.896, T _max = 0.915
11643 measured reflections
2200 independent reflections
1717 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.093
S = 1.08
2200 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810010767/pv2269sup1.cif

e-66-0o953-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010767/pv2269Isup2.hkl

e-66-0o953-Isup2.hkl^{(106KB, 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⋯O1ⁱ	0.82	1.90	2.7154 (12)	175

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the FIST–DST program at SSCU, IISc. We thank Professor T. N. Guru Row, IISc, Bangalore, for his help with the data collection. FNK thanks the DST for Fast Track Proposal funding.

supplementary crystallographic information

Comment

Montmorillonite clays have been found to effectively catalyze a broad range of chemical reactions (Roopan et al., 2009b). In continuation of our green chemical approach on the structural chemistry of disubstituted quinolines (Khan et al., 2010a,b; Roopan et al., 2009a), we have demonstarted the reduction of an aldehyde using Montmorillonite K-10 as a catalyst, to obtain the title alcohol. In this article, the crystal structure of the title molecule is presented.

In the title molecule (Fig. 1) all non-hydrogen atoms are coplanar (r.m.s deviation = 0.0266 Å); the C—C—C—O torsion angles are -0.9 (2) and -179.73 (13)°. The crystal structure is composed of discrete molecules with bond lengths and angles quite typical for compounds of this class and agree well with the corresponding bond lengths and angles reported for some related compounds (Khan et al., 2010a & 2010b; Roopan et al., 2009). In the crystal, symmetry related molecules are hydrogen bonded via intermolecular O—H···O type interactions forming one dimensional chains along the b-axis. In addition, an intramolecular interaction, C3—H3···O1 further consolidated the crystal structure.

Experimental

2-Chlorbenzo[h]quinoline-3-carbaldehyde (241 mg, 1 mmol), sodium borohydride (38 mg, 1 mmol) and a catalytic amount of montmorillonite K-10 (100 mg) were placed in a beaker. The contents were irradiated at 500 W for 5 min. The product was dissolved in ethyl acetate and the residue removed by filtration. The filtrate was subjected to column chromatography on silica, and ethyl acetate/petroleum ether was used as the eluant. The solvent was evaporated and the residue recrystallized from chloroform to give colorless crystals.