organic compounds
[2-(Biphenyl-4-yl)-1,3-thiazol-4-yl]methanol
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
*Correspondence e-mail: jjasinski@keene.edu
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
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell 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.
Supporting information
https://doi.org/10.1107/S1600536812039062/is5193sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039062/is5193Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812039062/is5193Isup3.cml
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
(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 (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).All of the H atoms were placed in their calculated positions and then refined using the riding model with O—H = 0.82 Å and C—H = 0.93 Å (CH) or 0.97 Å (CH2). The Uiso(H) values were set to 1.5Ueq(O) and 1.2Ueq(C).
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
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).
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).
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
CrysAlis PRO (Oxford Diffraction, 2010); 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 (Sheldrick, 2008).C16H13NOS | F(000) = 560 |
Mr = 267.33 | Dx = 1.390 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2ybc | Cell parameters from 3467 reflections |
a = 6.05424 (18) Å | θ = 3.0–72.5° |
b = 29.3096 (9) Å | µ = 2.16 mm−1 |
c = 7.2064 (2) Å | T = 173 K |
β = 92.668 (3)° | Chunk, colorless |
V = 1277.37 (7) Å3 | 0.32 × 0.18 × 0.08 mm |
Z = 4 |
Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer | 2501 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 2232 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 72.6°, θmin = 3.0° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | k = −21→36 |
Tmin = 0.604, Tmax = 0.841 | l = −8→8 |
7600 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0662P)2 + 0.2333P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
2501 reflections | Δρmax = 0.30 e Å−3 |
174 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0044 (7) |
C16H13NOS | V = 1277.37 (7) Å3 |
Mr = 267.33 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 6.05424 (18) Å | µ = 2.16 mm−1 |
b = 29.3096 (9) Å | T = 173 K |
c = 7.2064 (2) Å | 0.32 × 0.18 × 0.08 mm |
β = 92.668 (3)° |
Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer | 2501 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | 2232 reflections with I > 2σ(I) |
Tmin = 0.604, Tmax = 0.841 | Rint = 0.050 |
7600 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.30 e Å−3 |
2501 reflections | Δρmin = −0.27 e Å−3 |
174 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.63121 (7) | 0.695240 (15) | 0.03840 (6) | 0.03231 (18) | |
O1 | −0.0110 (2) | 0.78873 (4) | −0.02845 (18) | 0.0324 (3) | |
H1 | 0.0382 | 0.7907 | −0.1323 | 0.049* | |
N1 | 0.2361 (2) | 0.70633 (4) | 0.14310 (19) | 0.0244 (3) | |
C1 | 0.1660 (3) | 0.78956 (6) | 0.1071 (3) | 0.0318 (4) | |
H1A | 0.1065 | 0.7906 | 0.2297 | 0.038* | |
H1B | 0.2524 | 0.8170 | 0.0911 | 0.038* | |
C2 | 0.3140 (3) | 0.74885 (5) | 0.0952 (2) | 0.0263 (4) | |
C3 | 0.5237 (3) | 0.74927 (6) | 0.0367 (2) | 0.0303 (4) | |
H3 | 0.5986 | 0.7753 | 0.0008 | 0.036* | |
C4 | 0.3844 (3) | 0.67462 (6) | 0.1183 (2) | 0.0243 (3) | |
C5 | 0.3507 (3) | 0.62588 (5) | 0.1571 (2) | 0.0240 (3) | |
C6 | 0.1540 (3) | 0.61063 (5) | 0.2309 (2) | 0.0267 (4) | |
H6 | 0.0440 | 0.6315 | 0.2567 | 0.032* | |
C7 | 0.1218 (3) | 0.56472 (6) | 0.2657 (2) | 0.0276 (4) | |
H7 | −0.0098 | 0.5552 | 0.3149 | 0.033* | |
C8 | 0.2835 (3) | 0.53247 (5) | 0.2284 (2) | 0.0244 (3) | |
C9 | 0.4796 (3) | 0.54796 (6) | 0.1556 (2) | 0.0269 (4) | |
H9 | 0.5901 | 0.5271 | 0.1312 | 0.032* | |
C10 | 0.5133 (3) | 0.59363 (6) | 0.1191 (2) | 0.0268 (4) | |
H10 | 0.6446 | 0.6030 | 0.0691 | 0.032* | |
C11 | 0.2501 (3) | 0.48303 (5) | 0.2655 (2) | 0.0249 (3) | |
C12 | 0.0471 (3) | 0.46207 (6) | 0.2234 (2) | 0.0298 (4) | |
H12 | −0.0698 | 0.4792 | 0.1725 | 0.036* | |
C13 | 0.0174 (3) | 0.41583 (6) | 0.2567 (3) | 0.0353 (4) | |
H13 | −0.1182 | 0.4022 | 0.2263 | 0.042* | |
C14 | 0.1890 (3) | 0.39001 (6) | 0.3349 (3) | 0.0351 (4) | |
H14 | 0.1686 | 0.3591 | 0.3588 | 0.042* | |
C15 | 0.3913 (3) | 0.41044 (6) | 0.3774 (2) | 0.0328 (4) | |
H15 | 0.5069 | 0.3932 | 0.4303 | 0.039* | |
C16 | 0.4223 (3) | 0.45643 (6) | 0.3414 (2) | 0.0281 (4) | |
H16 | 0.5598 | 0.4697 | 0.3682 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0217 (3) | 0.0331 (3) | 0.0429 (3) | 0.00099 (15) | 0.00883 (18) | 0.00499 (17) |
O1 | 0.0255 (6) | 0.0324 (7) | 0.0403 (7) | 0.0036 (5) | 0.0110 (5) | 0.0055 (5) |
N1 | 0.0228 (7) | 0.0239 (7) | 0.0267 (7) | −0.0004 (5) | 0.0034 (5) | 0.0000 (5) |
C1 | 0.0367 (10) | 0.0228 (8) | 0.0363 (9) | 0.0001 (7) | 0.0074 (7) | 0.0000 (7) |
C2 | 0.0275 (8) | 0.0255 (8) | 0.0259 (8) | −0.0023 (6) | 0.0019 (6) | 0.0002 (6) |
C3 | 0.0286 (9) | 0.0294 (9) | 0.0330 (8) | −0.0040 (7) | 0.0038 (7) | 0.0040 (6) |
C4 | 0.0212 (8) | 0.0277 (8) | 0.0243 (8) | −0.0007 (6) | 0.0024 (6) | −0.0005 (6) |
C5 | 0.0238 (8) | 0.0249 (8) | 0.0231 (7) | 0.0011 (6) | 0.0003 (6) | −0.0004 (6) |
C6 | 0.0216 (8) | 0.0264 (8) | 0.0322 (8) | 0.0045 (6) | 0.0037 (6) | −0.0015 (6) |
C7 | 0.0221 (8) | 0.0295 (8) | 0.0316 (8) | −0.0005 (6) | 0.0042 (6) | −0.0011 (6) |
C8 | 0.0253 (8) | 0.0253 (8) | 0.0223 (7) | 0.0007 (6) | −0.0006 (6) | −0.0011 (6) |
C9 | 0.0249 (8) | 0.0280 (8) | 0.0280 (8) | 0.0059 (6) | 0.0038 (6) | −0.0013 (6) |
C10 | 0.0217 (8) | 0.0300 (8) | 0.0290 (8) | 0.0013 (6) | 0.0051 (6) | 0.0007 (6) |
C11 | 0.0272 (8) | 0.0253 (8) | 0.0223 (7) | 0.0006 (6) | 0.0035 (6) | −0.0023 (6) |
C12 | 0.0280 (9) | 0.0296 (8) | 0.0320 (8) | 0.0000 (7) | 0.0025 (7) | −0.0005 (7) |
C13 | 0.0330 (9) | 0.0346 (9) | 0.0390 (10) | −0.0080 (7) | 0.0081 (8) | −0.0035 (7) |
C14 | 0.0460 (11) | 0.0249 (8) | 0.0353 (9) | −0.0038 (7) | 0.0125 (8) | 0.0012 (7) |
C15 | 0.0383 (10) | 0.0286 (9) | 0.0316 (9) | 0.0045 (7) | 0.0038 (7) | 0.0022 (7) |
C16 | 0.0278 (8) | 0.0270 (8) | 0.0295 (8) | 0.0017 (6) | 0.0009 (7) | −0.0021 (6) |
S1—C3 | 1.7120 (18) | C7—H7 | 0.9300 |
S1—C4 | 1.7350 (16) | C8—C9 | 1.396 (2) |
O1—C1 | 1.416 (2) | C8—C11 | 1.489 (2) |
O1—H1 | 0.8200 | C9—C10 | 1.381 (2) |
N1—C4 | 1.310 (2) | C9—H9 | 0.9300 |
N1—C2 | 1.382 (2) | C10—H10 | 0.9300 |
C1—C2 | 1.497 (2) | C11—C16 | 1.393 (2) |
C1—H1A | 0.9700 | C11—C12 | 1.395 (2) |
C1—H1B | 0.9700 | C12—C13 | 1.390 (3) |
C2—C3 | 1.356 (2) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—C14 | 1.384 (3) |
C4—C5 | 1.472 (2) | C13—H13 | 0.9300 |
C5—C6 | 1.400 (2) | C14—C15 | 1.385 (3) |
C5—C10 | 1.400 (2) | C14—H14 | 0.9300 |
C6—C7 | 1.384 (2) | C15—C16 | 1.387 (2) |
C6—H6 | 0.9300 | C15—H15 | 0.9300 |
C7—C8 | 1.396 (2) | C16—H16 | 0.9300 |
C3—S1—C4 | 89.51 (8) | C9—C8—C7 | 117.93 (15) |
C1—O1—H1 | 109.5 | C9—C8—C11 | 120.60 (15) |
C4—N1—C2 | 111.18 (14) | C7—C8—C11 | 121.47 (15) |
O1—C1—C2 | 112.47 (14) | C10—C9—C8 | 121.50 (15) |
O1—C1—H1A | 109.1 | C10—C9—H9 | 119.3 |
C2—C1—H1A | 109.1 | C8—C9—H9 | 119.3 |
O1—C1—H1B | 109.1 | C9—C10—C5 | 120.37 (16) |
C2—C1—H1B | 109.1 | C9—C10—H10 | 119.8 |
H1A—C1—H1B | 107.8 | C5—C10—H10 | 119.8 |
C3—C2—N1 | 114.92 (15) | C16—C11—C12 | 118.34 (15) |
C3—C2—C1 | 125.59 (15) | C16—C11—C8 | 120.65 (15) |
N1—C2—C1 | 119.48 (15) | C12—C11—C8 | 121.01 (15) |
C2—C3—S1 | 110.52 (13) | C13—C12—C11 | 120.78 (16) |
C2—C3—H3 | 124.7 | C13—C12—H12 | 119.6 |
S1—C3—H3 | 124.7 | C11—C12—H12 | 119.6 |
N1—C4—C5 | 124.12 (15) | C14—C13—C12 | 120.21 (17) |
N1—C4—S1 | 113.86 (12) | C14—C13—H13 | 119.9 |
C5—C4—S1 | 122.01 (12) | C12—C13—H13 | 119.9 |
C6—C5—C10 | 118.46 (15) | C13—C14—C15 | 119.53 (16) |
C6—C5—C4 | 120.64 (14) | C13—C14—H14 | 120.2 |
C10—C5—C4 | 120.89 (15) | C15—C14—H14 | 120.2 |
C7—C6—C5 | 120.57 (15) | C14—C15—C16 | 120.35 (17) |
C7—C6—H6 | 119.7 | C14—C15—H15 | 119.8 |
C5—C6—H6 | 119.7 | C16—C15—H15 | 119.8 |
C6—C7—C8 | 121.15 (16) | C15—C16—C11 | 120.78 (16) |
C6—C7—H7 | 119.4 | C15—C16—H16 | 119.6 |
C8—C7—H7 | 119.4 | C11—C16—H16 | 119.6 |
C4—N1—C2—C3 | −1.0 (2) | C6—C7—C8—C11 | 179.99 (15) |
C4—N1—C2—C1 | 177.81 (14) | C7—C8—C9—C10 | −0.8 (2) |
O1—C1—C2—C3 | 109.65 (19) | C11—C8—C9—C10 | 179.58 (14) |
O1—C1—C2—N1 | −69.1 (2) | C8—C9—C10—C5 | 0.9 (2) |
N1—C2—C3—S1 | 0.46 (19) | C6—C5—C10—C9 | −0.6 (2) |
C1—C2—C3—S1 | −178.31 (14) | C4—C5—C10—C9 | −179.82 (14) |
C4—S1—C3—C2 | 0.15 (13) | C9—C8—C11—C16 | 40.4 (2) |
C2—N1—C4—C5 | 179.93 (14) | C7—C8—C11—C16 | −139.27 (17) |
C2—N1—C4—S1 | 1.14 (17) | C9—C8—C11—C12 | −138.87 (17) |
C3—S1—C4—N1 | −0.76 (13) | C7—C8—C11—C12 | 41.5 (2) |
C3—S1—C4—C5 | −179.58 (14) | C16—C11—C12—C13 | 0.1 (2) |
N1—C4—C5—C6 | −2.2 (2) | C8—C11—C12—C13 | 179.39 (15) |
S1—C4—C5—C6 | 176.53 (12) | C11—C12—C13—C14 | 0.9 (3) |
N1—C4—C5—C10 | 177.08 (15) | C12—C13—C14—C15 | −0.9 (3) |
S1—C4—C5—C10 | −4.2 (2) | C13—C14—C15—C16 | −0.2 (3) |
C10—C5—C6—C7 | 0.1 (2) | C14—C15—C16—C11 | 1.3 (3) |
C4—C5—C6—C7 | 179.41 (15) | C12—C11—C16—C15 | −1.2 (2) |
C5—C6—C7—C8 | 0.0 (3) | C8—C11—C16—C15 | 179.52 (15) |
C6—C7—C8—C9 | 0.3 (2) |
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 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H13NOS |
Mr | 267.33 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 6.05424 (18), 29.3096 (9), 7.2064 (2) |
β (°) | 92.668 (3) |
V (Å3) | 1277.37 (7) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 2.16 |
Crystal size (mm) | 0.32 × 0.18 × 0.08 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur (Eos, Gemini) |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.604, 0.841 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7600, 2501, 2232 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.619 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.114, 1.05 |
No. of reflections | 2501 |
No. of parameters | 174 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.27 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x+1, y, z. |
Acknowledgements
MK thanks UOM for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.
References
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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).