2-(6-Benzoyl-2-oxo-1,3-benzothia­zol-3-yl)acetic acid

Abdullah Aydın; Mehmet Akkurt; Tijen Önkol; Orhan Büyükgüngör; M Fethi Şahin

doi:10.1107/S160053680905329X

. 2009 Dec 16;66(Pt 1):o168. doi: 10.1107/S160053680905329X

2-(6-Benzoyl-2-oxo-1,3-benzothiazol-3-yl)acetic acid

Abdullah Aydın ^a,^*, Mehmet Akkurt ^b,^‡, Tijen Önkol ^c, Orhan Büyükgüngör ^d, M Fethi Şahin ^c

PMCID: PMC2980097 PMID: 21580054

Abstract

In the title compound, C₁₆H₁₁NO₄S, the nine-membered fused ring is nearly planar, with maximum deviations from the mean plane of −0.022 (1) Å for the N atom and 0.011 (1) Å for the S atom, and makes a dihedral angle of 53.56 (7)° with the phenyl ring. The crystal structure is stabilized by O—H⋯O and C—H⋯O hydrogen-bonding interactions.

Related literature

For the pharmacological effects of 2-benzoxazolinone/benzothiazolinone derivatives, see: Ünlü et al. (2003 ▶); Petrov et al. (1994 ▶). For the quantum-chemical calculations, see: Pople & Beveridge (1970 ▶).

Experimental

Crystal data

C₁₆H₁₁NO₄S
M _r = 313.33
Orthorhombic,
a = 11.4248 (3) Å
b = 8.9155 (2) Å
c = 27.6280 (8) Å
V = 2814.13 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.59 × 0.38 × 0.17 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.868, T _max = 0.959
31503 measured reflections
3006 independent reflections
2363 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.084
S = 1.04
3006 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); 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 datablocks global, I. DOI: 10.1107/S160053680905329X/hg2616sup1.cif

e-66-0o168-sup1.cif^{(21.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905329X/hg2616Isup2.hkl

e-66-0o168-Isup2.hkl^{(144.6KB, hkl)}

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
O4—H4A⋯O1ⁱ	0.82	1.86	2.6315 (18)	157
C9—H9⋯O2ⁱⁱ	0.93	2.43	3.1233 (19)	131
C15—H15B⋯O3ⁱⁱⁱ	0.97	2.54	3.416 (2)	150

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

supplementary crystallographic information

Comment

2-Benzoxazolinone / benzothiazolinone derivatives exhibit a variety of pharmacological effects, including anlgesic and anti-inflammatory activity (Ünlü et al., 2003). It was studied analgesic and anti-inflammatory activity of the title compound which was synthesized by (Petrov et al., 1994) previously. Based on this study, the title compound, (I), showed close anlgesic activity that of aspirin at 100 mg/kg dose, but in terms of anti-inflammatory activity, inactive (Ünlü et al., 2003). In this study, the structure of the title compound (I) has been determined by single-crystal X-ray diffraction.

In (I) (Fig. 1), the nine-membered ring S1/N1/C8–C14 is nearly planar with maximum deviations of -0.022 (1) Å for N1 and 0.011 (1) Å for S1 from the mean plane. The dihedral angle between the nine-membered ring and the phenyl ring C1–C6 is 53.56 (7)° [the calculated value is 74.47°, using the CNDO (Pople et al., 1970) aproximation]. The N1—C15—C16—O3 and N1—C15—C16—O4 torsion angles related with the carboxyl group are 0.7 (3) and -177.21 (15)° [the calculated values are 114.5° and -65.95°].

In the crystal structure of (I), there exist intermolecular O—H···O and C—H···O hydrogen bonding interactions (Table 1, Fig. 2).

The quantum-chemical calculation of (I) was carried out by using the CNDO aproximation. The HOMO and LUMO energy levels of (I) are -10.4385 and 2.0553 eV, respectively. Its calculated molecule dipole moment is 8.206 Debye (1 D = 3.33564 × 10 ^-30 C.m.). Due to the intermolecular interactions in the crystal structure of (I), the spatial configurations obtained by the theoretical CNDO and experimental X-rays for (I) are almost different (see Figs. 1 & 3). But the geometric parameters in (I) are almost comparable within the experimental error interval in the results of both methods.

Experimental

Methyl (6-benzoyl-2-oxo-1,3-benzothiazol-3-yl)acetate (2 mmol) and sodium hydroxide (2 mmol) in 30 ml e thanol/water (25:5) was refluxed for 4 h. After cooling to room temperature, the mixture was acidified with 1 N HCl (30 ml) to give a solid precipitate.The product was collected by suction filtration, washed with water, dried, and crystallized from ethanol/water to yield % 73 [m.p.: 524 K].