[2-(Biphenyl-4-yl)-1,3-thia­zol-4-yl]methanol

Manpreet Kaur; Jerry P Jasinski; Amanda C Keeley; H S Yathirajan

doi:10.1107/S1600536812039062

. 2012 Sep 19;68(Pt 10):o2950. doi: 10.1107/S1600536812039062

[2-(Biphenyl-4-yl)-1,3-thiazol-4-yl]methanol

Manpreet Kaur ^a, Jerry P Jasinski ^b,^*, Amanda C Keeley ^b, H S Yathirajan ^a

PMCID: PMC3470322 PMID: 23125735

Abstract

In the title compound, C₁₆H₁₃NOS, the central benzene ring makes dihedral angles of 3.25 (7) and 41.32 (8)°, respectively, with the thiazole and phenyl rings. In the crystal, O—H⋯N hydrogen bonds link the molecules into a chain along the c axis. A weak C—H⋯O interaction further connects the chains into a layer parallel to the ac plane.

Related literature

For pharmacological applications of thiazole derivatives, see: Bishayee et al. (1997 ▶); Bhattacharya et al. (2005 ▶); Sharma et al. (2009 ▶). For the preparation of the title compound, see: Miyaura et al. (1979 ▶); Finholt et al. (1947 ▶). For related structures, see: Ghabbour, Chia et al. (2012 ▶); Ghabbour, Kadi et al. (2012 ▶); Hökelek et al. (2006 ▶); Yathirajan et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₃NOS
M _r = 267.33
Monoclinic,
a = 6.05424 (18) Å
b = 29.3096 (9) Å
c = 7.2064 (2) Å
β = 92.668 (3)°
V = 1277.37 (7) Å³
Z = 4
Cu Kα radiation
μ = 2.16 mm⁻¹
T = 173 K
0.32 × 0.18 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T _min = 0.604, T _max = 0.841
7600 measured reflections
2501 independent reflections
2232 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.114
S = 1.05
2501 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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) global, I. DOI: 10.1107/S1600536812039062/is5193sup1.cif

e-68-o2950-sup1.cif^{(22.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039062/is5193Isup2.hkl

e-68-o2950-Isup2.hkl^{(122.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812039062/is5193Isup3.cml

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⋯N1ⁱ	0.82	2.06	2.8618 (19)	166
C3—H3⋯O1ⁱⁱ	0.93	2.42	3.101 (2)	131

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

Acknowledgments

MK thanks UOM for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

Thiazole containing drugs have widespread use in a variety of medical conditions such as fungal and bacterial infections, gastric ulcers, cancer, etc (Bishayee et al., 1997). Thiazole derivatives are involved frequently as the subject of drug design and synthesis efforts and they are reported to possess several activities like antibacterial, antifungal, anti-inflammatory (Sharma et al., 2009), analgesic, antitubercular, central nervous system (CNS) stimmulant activity as well as anti-HIV activity (Bhattacharya et al., 2005). Crystal structures of some thiazole derivatives, viz., 3-(2-bromo-5-methoxyphenyl)-5-methyl-1-(4-phenyl-1,3-thiazol-2-yl) -1H-1,2,4-triazole (Yathirajan et al., 2006), 2-amino-4-(4-methoxyphenyl)-1,3-thiazole (Hökelek et al., 2006), 5-bromo-4-(3,4-dimethoxyphenyl)thiazol-2-amine (Ghabbour, Chia et al., 2012) and N-[4-(4-bromophenyl)thiazol-2-yl]-4-(piperidin-1-yl)butanamide (Ghabbour, Kadi et al., 2012) have been reported. In view of the importance of thiazoles, this paper reports the crystal structure of the title compound, (I), C₁₆H₁₃NOS.

In the title compound, (I), the dihedral angle between least-squares planes of the planar thiazole-phenyl unit (C2/C3/S1/C4/N1/C5–C10) and the outer phenyl ring (C11–C16) is 39.9 (5)° (Fig. 1). Bond lengths are in normal ranges (Allen et al., 1987). O—H···N hydrogen bonds and weak C—H···O intermolecular interactions are observed which contribute to crystal packing forming a layer parallel to the ac plane (Fig. 2).

Experimental

The title compound was prepared by the following procedure (Miyaura et al., 1979; Finholt et al., 1947). A mixture of 2-bromo-thiazole-4-carboxylic acid ethyl ester (1 g, 4.24 mmol), biphenyl boronic acid (1 g, 5.08 mmol), Xantphos (122.54 mg,0.212 mmol), tripotassium phosphate (2.6 g, 12.71 mmol) and palladium acetate (47.55 mg, 0.212 mmol) in THF as solvent was degassed for 15 mins and sealed. The sealed tube was heated at 383 K for 16 h under N₂ atmosphere. After completion, the reaction mixture was diluted with ethyl acetate and filtered through a celite bed. It was then quenched with water and extracted with ethyl acetate. Organic layers were collected, dried over sodium sulphate and concentrated. Crude mass was purified through silica gel column chromatography (60:120 mesh) using 30% ethyl acetate in petroleum ether to afford 2-biphenyl-4-yl-thiazole-4-carboxylic acid ethyl ester (80% yield). Lithium aluminium hydride (122 mg, 3.23 mmol) was dissolved in minimum amount of THF in a RB flask and cooled to 0 °C under N₂ atmosphere (Fig. 3). To this was added drop-wise a solution of 2-biphenyl-4-yl-thiazole-4-carboxylic acid ethyl ester (1 g, 3.23 mmol) in THF and stirred the reaction mixture for an hour. After completion of reaction, the reaction mixture was quenched with 10% sodium carbonate solution at 273 K and extracted with ethyl acetate. Organic layers were collected, dried over sodium sulphate and concentrated. Crude mass was purified through silica gel column chromatography (60:120 mesh) using 40% ethyl acetate in petroleum ether to afford the title compound (93% yield). X-ray quality crystals were obtained by slow evaporation of ethyl acetate solution (m.p.: 423–426 K).