[2-(Biphenyl-4-yl)-1,3-thia-zol-4-yl]methanol.

In the title compound, C(16)H(13)NOS, the central benzene ring makes dihedral angles of 3.25 (7) and 41.32 (8)°, respectively, with the thia-zole and phenyl rings. In the crystal, O-H⋯N hydrogen bonds link the mol-ecules into a chain along the c axis. A weak C-H⋯O inter-action 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 = 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

Δρmax = 0.30 e Å−3

Δρmin = −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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039062/is5193sup1.cif

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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)

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

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

Symmetry codes: (i) ; (ii) .