2-(2-Hy-droxy-phen-yl)-1,3-benzothia-zole-6-carbaldehyde.

The mol-ecule of the title compound, C(14)H(9)NO(2)S, is nearly planar, the maximum atomic deviation being 0.081 (2) Å. An intra-molecular O-H⋯N bond generates an S(6) ring motif. In the crystal, inversion-related mol-ecules linked by a pair of weak C-H⋯O hydrogen bonds form a supra-molecular dimer. π-π stacking is observed between the thia-zole and benzene rings of adjacent mol-ecules, the centroid-centroid distance being 3.7679 (9) Å.

Related literature

For the spectroscopy and preparation of the title compound, see: Hsieh et al. (2008 ▶). For the spectroscopy and applications of benzoxazole and benzothia­zole derivatives, see: Chen & Pang (2009 ▶, 2010 ▶); Hrobáriková et al. (2010 ▶); Kim et al. (2010a ▶,b ▶); Lijima et al. (2010 ▶); Lim et al. (2011 ▶); López-Ruiz et al. (2011 ▶); Tanaka et al. (2001 ▶). For related structures, see: Tong (2005 ▶); Hahn et al. (1998 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H9NO2S

M = 255.28

Monoclinic,

a = 8.2645 (3) Å

b = 5.6449 (2) Å

c = 23.8341 (9) Å

β = 98.147 (2)°

V = 1100.69 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 150 K

0.38 × 0.14 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.882, T max = 0.992

8427 measured reflections

1943 independent reflections

1333 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.058

S = 0.90

1943 reflections

168 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040712/xu5345sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040712/xu5345Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040712/xu5345Isup3.cml

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

C14H9NO2S	F(000) = 528
Mr = 255.28	Dx = 1.541 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 2297 reflections
a = 8.2645 (3) Å	θ = 2.5–25.7°
b = 5.6449 (2) Å	µ = 0.29 mm−1
c = 23.8341 (9) Å	T = 150 K
β = 98.147 (2)°	Plate, yellow
V = 1100.69 (7) Å3	0.38 × 0.14 × 0.04 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1943 independent reflections
Radiation source: fine-focus sealed tube	1333 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.882, Tmax = 0.992	k = −6→3
8427 measured reflections	l = −28→28

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.058	w = 1/[σ2(Fo2) + (0.0251P)2] where P = (Fo2 + 2Fc2)/3
S = 0.90	(Δ/σ)max < 0.001
1943 reflections	Δρmax = 0.22 e Å−3
168 parameters	Δρmin = −0.27 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (2)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
S	0.74344 (6)	0.79801 (8)	0.392532 (18)	0.02213 (16)
O1	0.51794 (15)	0.6205 (2)	0.59718 (5)	0.0317 (4)
O2	1.05490 (15)	1.4470 (2)	0.35839 (5)	0.0272 (3)
N1	0.88683 (16)	1.1973 (2)	0.42282 (6)	0.0183 (3)
C1	0.81872 (19)	1.1165 (3)	0.46928 (7)	0.0167 (4)
C2	0.7362 (2)	0.8986 (3)	0.46067 (7)	0.0169 (4)
C3	0.66326 (19)	0.7940 (3)	0.50315 (7)	0.0189 (4)
H3	0.6076	0.6510	0.4970	0.023*
C4	0.67509 (19)	0.9071 (3)	0.55528 (7)	0.0183 (4)
C5	0.7578 (2)	1.1247 (3)	0.56406 (7)	0.0211 (4)
H5	0.7644	1.1987	0.5992	0.025*
C6	0.82896 (19)	1.2299 (3)	0.52162 (7)	0.0204 (4)
H6	0.8830	1.3741	0.5277	0.024*
C7	0.5997 (2)	0.7988 (3)	0.60128 (7)	0.0252 (4)
H7	0.6162	0.8736	0.6364	0.030*
C11	0.91907 (19)	1.0821 (3)	0.32631 (7)	0.0168 (4)
C12	1.0157 (2)	1.2802 (3)	0.31764 (7)	0.0190 (4)
C13	1.07588 (19)	1.3083 (3)	0.26659 (7)	0.0219 (4)
H13	1.1400	1.4394	0.2611	0.026*
C14	1.04146 (19)	1.1439 (3)	0.22413 (7)	0.0229 (5)
H14	1.0826	1.1644	0.1901	0.027*
C15	0.9459 (2)	0.9477 (3)	0.23149 (7)	0.0239 (5)
H15	0.9225	0.8371	0.2026	0.029*
C16	0.8862 (2)	0.9183 (3)	0.28209 (7)	0.0222 (4)
H16	0.8223	0.7863	0.2870	0.027*
C17	0.85778 (19)	1.0478 (3)	0.38021 (7)	0.0180 (4)
H2	1.005 (2)	1.407 (4)	0.3877 (7)	0.071 (8)*

	U11	U22	U33	U12	U13	U23
S	0.0278 (3)	0.0195 (3)	0.0199 (3)	−0.0044 (2)	0.0062 (2)	−0.0013 (2)
O1	0.0349 (8)	0.0318 (8)	0.0295 (8)	−0.0074 (7)	0.0085 (7)	0.0053 (6)
O2	0.0346 (8)	0.0245 (8)	0.0233 (8)	−0.0092 (6)	0.0070 (7)	−0.0026 (6)
N1	0.0198 (9)	0.0164 (8)	0.0186 (8)	0.0005 (7)	0.0025 (7)	0.0009 (7)
C1	0.0154 (10)	0.0160 (10)	0.0181 (10)	0.0040 (8)	0.0003 (8)	0.0037 (8)
C2	0.0172 (10)	0.0169 (10)	0.0165 (10)	0.0029 (8)	0.0016 (8)	0.0006 (8)
C3	0.0162 (10)	0.0168 (10)	0.0233 (11)	0.0011 (8)	0.0016 (8)	0.0021 (9)
C4	0.0170 (10)	0.0194 (10)	0.0187 (10)	0.0043 (8)	0.0034 (8)	0.0037 (8)
C5	0.0226 (11)	0.0225 (11)	0.0179 (11)	0.0051 (9)	0.0019 (9)	−0.0020 (8)
C6	0.0209 (11)	0.0178 (10)	0.0220 (11)	−0.0004 (8)	0.0011 (8)	−0.0001 (8)
C7	0.0241 (12)	0.0299 (11)	0.0215 (11)	0.0069 (10)	0.0030 (9)	0.0008 (9)
C11	0.0162 (10)	0.0173 (10)	0.0171 (10)	0.0008 (8)	0.0028 (8)	0.0023 (8)
C12	0.0183 (10)	0.0184 (10)	0.0194 (10)	0.0019 (9)	−0.0003 (8)	−0.0006 (9)
C13	0.0207 (11)	0.0220 (10)	0.0233 (11)	−0.0037 (8)	0.0048 (9)	0.0048 (9)
C14	0.0202 (11)	0.0292 (12)	0.0201 (11)	0.0032 (9)	0.0060 (9)	0.0051 (9)
C15	0.0279 (12)	0.0240 (11)	0.0198 (11)	0.0016 (9)	0.0040 (9)	−0.0030 (8)
C16	0.0238 (11)	0.0184 (10)	0.0244 (11)	−0.0023 (9)	0.0038 (9)	0.0011 (9)
C17	0.0146 (10)	0.0163 (10)	0.0228 (11)	0.0030 (8)	0.0016 (8)	0.0022 (8)

S—C2	1.7296 (16)	C5—H5	0.9300
S—C17	1.7454 (17)	C6—H6	0.9300
O1—C7	1.2087 (19)	C7—H7	0.9300
O2—C12	1.3588 (19)	C11—C16	1.400 (2)
O2—H2	0.890 (14)	C11—C12	1.406 (2)
N1—C17	1.3160 (18)	C11—C17	1.459 (2)
N1—C1	1.3882 (19)	C12—C13	1.387 (2)
C1—C6	1.394 (2)	C13—C14	1.373 (2)
C1—C2	1.407 (2)	C13—H13	0.9300
C2—C3	1.382 (2)	C14—C15	1.386 (2)
C3—C4	1.388 (2)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.376 (2)
C4—C5	1.407 (2)	C15—H15	0.9300
C4—C7	1.469 (2)	C16—H16	0.9300
C5—C6	1.375 (2)
C2—S—C17	89.10 (8)	C4—C7—H7	117.4
C12—O2—H2	107.2 (14)	C16—C11—C12	117.93 (15)
C17—N1—C1	110.79 (14)	C16—C11—C17	121.39 (15)
N1—C1—C6	125.67 (16)	C12—C11—C17	120.67 (15)
N1—C1—C2	114.43 (15)	O2—C12—C13	117.94 (15)
C6—C1—C2	119.88 (16)	O2—C12—C11	121.94 (15)
C3—C2—C1	121.30 (16)	C13—C12—C11	120.11 (16)
C3—C2—S	128.62 (14)	C14—C13—C12	120.42 (16)
C1—C2—S	110.07 (12)	C14—C13—H13	119.8
C2—C3—C4	118.44 (16)	C12—C13—H13	119.8
C2—C3—H3	120.8	C13—C14—C15	120.61 (16)
C4—C3—H3	120.8	C13—C14—H14	119.7
C3—C4—C5	120.40 (16)	C15—C14—H14	119.7
C3—C4—C7	119.55 (16)	C16—C15—C14	119.28 (16)
C5—C4—C7	120.05 (16)	C16—C15—H15	120.4
C6—C5—C4	121.13 (16)	C14—C15—H15	120.4
C6—C5—H5	119.4	C15—C16—C11	121.64 (16)
C4—C5—H5	119.4	C15—C16—H16	119.2
C5—C6—C1	118.84 (16)	C11—C16—H16	119.2
C5—C6—H6	120.6	N1—C17—C11	123.12 (15)
C1—C6—H6	120.6	N1—C17—S	115.59 (12)
O1—C7—C4	125.29 (17)	C11—C17—S	121.27 (12)
O1—C7—H7	117.4

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.89 (2)	1.81 (2)	2.6228 (18)	150 (2)
C5—H5···O2i	0.93	2.61	3.293 (2)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.89 (2)	1.81 (2)	2.6228 (18)	150 (2)
C5—H5⋯O2i	0.93	2.61	3.293 (2)	130

Symmetry code: (i) .