2-[1,1-Dioxo-2-(2,4,5-trifluoro­benz­yl)-2H-1,2-benzothia­zin-4-yl]acetic acid

Yanchun Yang; Youzhu Yu; Changjin Zhu

doi:10.1107/S1600536812015942

. 2012 Apr 13;68(Pt 5):o1364. doi: 10.1107/S1600536812015942

2-[1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-2H-1,2-benzothiazin-4-yl]acetic acid

Yanchun Yang ^a, Youzhu Yu ^b, Changjin Zhu ^a,^*

PMCID: PMC3344496 PMID: 22590258

Abstract

In the title compound, C₁₇H₁₂F₃NO₄S, the heterocyclic thiazine ring adopts a half-chair conformation with the S and the N atoms displaced by −0.608 (3) and 0.105 (3) Å, respectively, from the mean plane formed by the remaining ring atoms. The dihedral angle between the two benzene rings is 36.63 (8)° and the acetic acid group is inclined at right angles [89.78 (8) °] to the mean plane formed by the C atoms of the thiazine ring. The crystal structure features O—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For pharmaceuticals properties of benzothiazines, see: Zia-ur-Rehman et al. (2006 ▶). For synthetic details of the title compound, see: Chen et al. (2011 ▶). For related structures, see: Ahmad et al. (2008 ▶); Zia-ur-Rehman et al. (2008 ▶).

Experimental

Crystal data

C₁₇H₁₂F₃NO₄S
M _r = 383.34
Monoclinic,
a = 8.3290 (17) Å
b = 23.141 (5) Å
c = 8.6692 (17) Å
β = 90.93 (3)°
V = 1670.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
22476 measured reflections
4158 independent reflections
3646 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.108
S = 1.03
4158 reflections
239 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015942/pv2523sup1.cif

e-68-o1364-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015942/pv2523Isup2.hkl

e-68-o1364-Isup2.hkl^{(203.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812015942/pv2523Isup3.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
O1—H1⋯O2ⁱ	0.84 (3)	1.83 (3)	2.675 (2)	179 (3)
C8—H8⋯O3ⁱⁱ	0.93	2.55	3.211 (2)	129
C9—H9A⋯O3ⁱⁱ	0.97	2.30	3.207 (2)	155
C11—H11B⋯O4ⁱⁱⁱ	0.97	2.40	3.162 (2)	135

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

Acknowledgments

This work was supported by the Beijing Natural Science Foundation (No. 7102091) and the Research Fund for the Doctoral Program of Higher Education of China (No. 20111101110042).

supplementary crystallographic information

Comment

Benzothiazine moiety is present as the skeletal structure in several pharmaceuticals such as antibacterial, diuretic, hypoglycemic, antithyroid, and antitumor drugs (Zia-ur-Rehman et al., 2006). In this article, we report the crystal structure of the title compound which has been used as aldose reductase inhibitor (Chen et al., 2011).

In the title compound (Fig. 1), the heterocyclic thiazine ring adopts a half chair conformation with the S1 and the N1 atoms displaced by -0.608 (3) and 0.105 (3) Å, respectively, from the mean plane formed by the remaining ring atoms (C1/C6/C7/C8). The dihedral angle between the two benze rings (C1–C6) and (C12–C17) is 36.63 (8)° and the acetate group (O1/O2/C9/C10) is inclined at right angles (89.78 (8) °) to the mean plane formed by the C-atoms of the thiazine ring. The crystal structure is stabilized by intermolecular O—H···O and C—H···O hydrogen bonds forming a three-dimensional network (Fig. 2).

Experimental

A mixture of methyl 2-(1,1-dioxido-2-(2,4,5-trifluorobenzyl)-2H-benzo[e][1,2] thiazin-4-yl)acetate (0.5 mmol), 1,4-dioxane (5 ml) and saturated aqueous sodium hydroxide (8 ml) was stirred at room temperature for 12 h. The alkaline suspension was adjusted to be acidic with 0.1 M HCl and extracted with ethyl acetate (3 x 30 ml). The combined organic layers were dried over MgSO₄ and filtered. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol (yield = 69%).