2-(2-Hy­droxy­phen­yl)-1,3-benzothia­zole-6-carbaldehyde

Kew-Yu Chen; Tzu-Chien Fang; Ming-Jen Chang; Hsing-Yang Tsai; Ming-Hui Luo

doi:10.1107/S1600536811040712

. 2011 Oct 8;67(Pt 11):o2862. doi: 10.1107/S1600536811040712

2-(2-Hydroxyphenyl)-1,3-benzothiazole-6-carbaldehyde

Kew-Yu Chen ^a,^*, Tzu-Chien Fang ^a, Ming-Jen Chang ^a, Hsing-Yang Tsai ^a, Ming-Hui Luo ^a

PMCID: PMC3247597 PMID: 22219902

Abstract

The molecule of the title compound, C₁₄H₉NO₂S, is nearly planar, the maximum atomic deviation being 0.081 (2) Å. An intramolecular O—H⋯N bond generates an S(6) ring motif. In the crystal, inversion-related molecules linked by a pair of weak C—H⋯O hydrogen bonds form a supramolecular dimer. π–π stacking is observed between the thiazole and benzene rings of adjacent molecules, 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 _r = 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
Δρ_max = 0.22 e Å⁻³
Δρ_min = −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 ▶).

Supplementary Material

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

e-67-o2862-sup1.cif^{(15.2KB, cif)}

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

e-67-o2862-Isup2.hkl^{(93.7KB, hkl)}

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

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the National Science Council and Feng Chia University in Taiwan.

supplementary crystallographic information

Comment

The excited-state intramolecular proton transfer (ESIPT) reaction of 2-(2-hydroxyphenyl)benzoxazole and 2-(2-hydroxyphenyl)benzothiazole derivatives has been investigated for past years (Hsieh et al., 2008; Kim et al., 2010a,b; Lijima et al., 2010; López-Ruiz et al., 2011), which incorporates transfer of a hydroxy proton to the imine nitrogen through a intramolecular six-membered-ring hydrogen-bonding system (Chen et al., 2009, 2010). The unusual photophysical property of the resulting proton-transfer tautomer has found many important applications (Hrobáriková et al., 2010; Lim et al., 2011; Tanaka et al., 2001).

The molecular structure of the title compound (HBT) is shown in Figure 1. The molecule is nearly planar, which is consistent with previous studies (Tong, 2005; Hahn et al., 1998). HBT possesses an intramolecular O—H···N hydrogen bond (Table 1), which generates an S(6) ring motif (Bernstein et al., 1995). In the crystal (Figure 2), inversion-related molecules are linked by a pair of weak C—H···O hydrogen bonds, forming a cyclic dimers with R₂²(18) graph-set motif. π-π stacing is observed between thiazole and C1ⁱ-benzene rings of adjacent molecules [symmetry code: (i): 2-x,2-y,1-z], the centroid-to-centroid distance being 3.7679 (9) Å.

Experimental

The title compound was synthesized according to the literature (Hsieh et al., 2008). Yellow needle-shaped crystals suitable for the crystallographic studies reported here were isolated over a period of five weeks by slow evaporation from the chloroform solution.