2-[(Z)-1,1-Dioxo-2-(2,4,5-tri­fluoro­benz­yl)-3,4-di­hydro-2H-1,2-benzo­thia­zin-4-yl­idene]acetic acid

Parveen, S.; Hussain, S.; Zhu, S.; Hao, X.; Zhu, C.

doi:10.1107/S1600536814008903

organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o627

doi:10.1107/S1600536814008903

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2-[(Z)-1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid

Shagufta Parveen,^a Saghir Hussain,^a Shaojuan Zhu,^a Xin Hao ^a and Changjin Zhu ^a ^*

^aSchool of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China
^*Correspondence e-mail: zcj@bit.edu.cn

(Received 1 April 2014; accepted 18 April 2014; online 3 May 2014)

In the title compound, C₁₇H₁₂F₃NO₄S, the heterocyclic thiazine ring adopts a half-chair conformation and the dihedral angle between the benzene rings is 43.28 (9)°. The α,β-unsaturated C=C group is inclined at an angle of 21.0 (3)° to the benzene ring of the benzothiazine moiety. In the crystal, inversion dimers linked by pairs of carboxylic acid O—H⋯O hydrogen bonds generate R₂²(8) loops. Each of the F atoms accepts a C_a—H⋯F (a = aromatic) hydrogen bond from an adjacent molecule, resulting in (001) sheets.

CCDC reference: 998389

Related literature

For pharmaceuticals properties of 1,2-benzothiazines, see: Lombardino et al. (1971 ); Turck et al. (1996 ); Zia-ur-Rehman et al. (2005 ). For the biological properties and synthetic details of the title compound, see: Parveen et al. (2014 ). For related structures, see: Ahmad et al. (2008 ); Zia-ur-Rehman et al. (2008 ); Yang et al. (2012 ). For graph-set analysis, see: Etter et al. (1990 ).

Experimental

Crystal data

C₁₇H₁₂F₃NO₄S
M_r = 383.34
Monoclinic, P 2₁ /n
a = 6.6085 (12) Å
b = 12.649 (3) Å
c = 18.757 (4) Å
β = 99.601 (2)°
V = 1545.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 153 K
0.31 × 0.21 × 0.07 mm

Data collection

Rigaku AFC10/Saturn724+ CCD-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ) T_min = 0.910, T_max = 0.970
13553 measured reflections
4123 independent reflections
3594 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.130
S = 1.00
4123 reflections
239 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4ⁱ	0.95 (3)	1.71 (3)	2.6454 (19)	170 (3)
C12—H12⋯F3ⁱⁱ	0.95	2.50	3.448 (2)	178
C15—H15⋯F1ⁱⁱⁱ	0.95	2.48	3.430 (2)	179
C5—H5⋯F2^iv	0.95	2.49	3.269 (2)	140
Symmetry codes: (i) -x, -y, -z; (ii) x+1, y, z; (iii) x-1, y, z; (iv) x, y-1, z.

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: CrystalStructure (Rigaku, 2008).

Supporting information

CCDC reference: 998389

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814008903/zs2294sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814008903/zs2294Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814008903/zs2294Isup3.mol

Supporting information file. DOI: 10.1107/S1600536814008903/zs2294Isup4.cml

checkCIF report

Comment top

Benzothiazine derivatives have been found to posses versatile biological activities such as anti-inflammatory, antioxidant and anti-bacterial (Lombardino et al., 1971; Zia-ur-Rehman et al., 2005). Derivatives of 1,2-benzothiazine-1,1-dioxide also reported as aldose reductase inhibitors (Parveen et al., 2014). We report here the structure of the title compound, C₁₇H₁₂F₃NO₄S, as an extension of this study. In this compound, (Fig. 1) the heterocyclic thiazine ring adopts a half chair conformation and the dihedral angle between the two benzene rings is 43.28 (9)°. The α,β-unsaturated C═C is inclined at an angle of 21.0 (3)° (torsion angle C5—C6—C7—C16) to the mean plane of the benzene ring (C1–C6). In the crystal, the molecules form centrosymmetric cyclic dimers through duplex intermolecular carboxylic acid O—H···O hydrogen bonds [graph set R²₂(8) (Etter et al., 1990)] (Table 1) while all of the fluorine atoms on the benzyl ring are involved in intermolecular aromatic C—H···F hydrogen-bonding interactions, giving a two-dimensional network structure lying parallel to (001) (Fig. 3).

Related literature top

For pharmaceuticals properties of 1,2-benzothiazines, see: Lombardino et al. (1971); Turck et al. (1996); Zia-ur-Rehman et al. (2005). For the biological properties and synthetic details of the title compound, see: Parveen et al. (2014). For related structures, see: Ahmad et al. (2008); Zia-ur-Rehman et al. (2008); Yang et al. (2012). For graph-set analysis, see: Etter et al. (1990).

Experimental top

A mixture of Z-2-[2-(2,4,5-trifluorobenzyl)-1,1-dioxido-2H-1,2-benzothiazin- 4(3H)-ylidene]acetic acid methyl ester (0.5 mmol), 1,4-dioxane (5 mL) and 10M hydrochloric acid (8 mL) was refluxed at 80°C for 12 h. The precipitate formed was then filtered and washed with cold water. The crude product was purified by flash chromatography. Crystals suitable for X-ray crystallography were obtained by slow evaporation of a solution of the title compound in ethanol (yield = 70%).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1998); software used to prepare material for publication: CrystalStructure (Rigaku, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the O—H···O and C—H···F hydrogen-bonding interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding are omitted for clarity.

2-[(Z)-1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid top

Crystal data top

C₁₇H₁₂F₃NO₄S	F(000) = 784
M_r = 383.34	D_x = 1.647 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.6085 (12) Å	Cell parameters from 5016 reflections
b = 12.649 (3) Å	θ = 2.2–29.1°
c = 18.757 (4) Å	µ = 0.27 mm⁻¹
β = 99.601 (2)°	T = 153 K
V = 1545.9 (5) Å³	Prism, colorless
Z = 4	0.31 × 0.21 × 0.07 mm

Data collection top

Rigaku AFC10/Saturn724+ CCD-detector diffractometer	4123 independent reflections
Radiation source: Rotating Anode	3594 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 28.5714 pixels mm^-1	θ_max = 29.1°, θ_min = 3.1°
ϕ and ω scans	h = −7→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −17→17
T_min = 0.910, T_max = 0.970	l = −24→25
13553 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0691P)² + 0.960P] where P = (F_o² + 2F_c²)/3
4123 reflections	(Δ/σ)_max = 0.001
239 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₇H₁₂F₃NO₄S	V = 1545.9 (5) Å³
M_r = 383.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.6085 (12) Å	µ = 0.27 mm⁻¹
b = 12.649 (3) Å	T = 153 K
c = 18.757 (4) Å	0.31 × 0.21 × 0.07 mm
β = 99.601 (2)°

Data collection top

Rigaku AFC10/Saturn724+ CCD-detector diffractometer	4123 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	3594 reflections with I > 2σ(I)
T_min = 0.910, T_max = 0.970	R_int = 0.033
13553 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.30 e Å⁻³
4123 reflections	Δρ_min = −0.46 e Å⁻³
239 parameters

Special details top

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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.77960 (7)	0.24006 (4)	0.22711 (2)	0.01907 (13)
F1	1.19907 (18)	0.38684 (10)	0.09496 (7)	0.0309 (3)
F2	0.9333 (2)	0.73151 (9)	0.06966 (8)	0.0356 (3)
F3	0.5560 (2)	0.65732 (11)	0.07640 (9)	0.0451 (4)
O1	0.6212 (2)	0.21803 (12)	0.26843 (8)	0.0274 (3)
O2	0.9255 (2)	0.32226 (11)	0.24924 (8)	0.0278 (3)
O3	0.2021 (2)	−0.09741 (11)	0.02713 (8)	0.0225 (3)
O4	0.1809 (2)	0.07828 (11)	0.04036 (8)	0.0236 (3)
N1	0.6674 (2)	0.26344 (12)	0.14388 (8)	0.0179 (3)
C1	0.9094 (3)	0.12210 (15)	0.21459 (9)	0.0184 (4)
C2	1.1103 (3)	0.10765 (16)	0.24959 (10)	0.0231 (4)
H2	1.1782	0.1613	0.2800	0.028*
C3	1.2102 (3)	0.01352 (17)	0.23936 (11)	0.0237 (4)
H3	1.3476	0.0024	0.2626	0.028*
C4	1.1085 (3)	−0.06389 (15)	0.19517 (11)	0.0221 (4)
H4	1.1748	−0.1295	0.1901	0.027*
C5	0.9114 (3)	−0.04731 (15)	0.15816 (10)	0.0195 (4)
H5	0.8469	−0.1005	0.1265	0.023*
C6	0.8059 (3)	0.04668 (14)	0.16672 (9)	0.0156 (3)
C7	0.5982 (3)	0.06696 (14)	0.12487 (9)	0.0161 (3)
C8	0.5169 (3)	0.18039 (14)	0.11740 (11)	0.0193 (4)
H8A	0.4635	0.1941	0.0657	0.023*
H8B	0.4000	0.1863	0.1440	0.023*
C9	0.8116 (3)	0.29315 (15)	0.09448 (11)	0.0208 (4)
H9A	0.7563	0.2682	0.0450	0.025*
H9B	0.9449	0.2576	0.1103	0.025*
C10	0.8449 (3)	0.41109 (14)	0.09298 (10)	0.0182 (4)
C11	1.0366 (3)	0.45337 (15)	0.09093 (10)	0.0195 (4)
C12	1.0725 (3)	0.56021 (16)	0.08396 (10)	0.0230 (4)
H12	1.2068	0.5864	0.0829	0.028*
C13	0.9075 (3)	0.62708 (15)	0.07861 (10)	0.0236 (4)
C14	0.7142 (3)	0.58847 (16)	0.08163 (12)	0.0262 (4)
C15	0.6818 (3)	0.48208 (16)	0.08880 (12)	0.0252 (4)
H15	0.5477	0.4567	0.0909	0.030*
C16	0.4816 (3)	−0.01466 (14)	0.09595 (10)	0.0186 (4)
H16	0.5364	−0.0838	0.1045	0.022*
C17	0.2763 (3)	−0.00501 (15)	0.05225 (10)	0.0184 (4)
H3O	0.064 (4)	−0.083 (2)	0.0060 (15)	0.043 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0204 (2)	0.0161 (2)	0.0201 (2)	−0.00048 (17)	0.00145 (17)	−0.00322 (16)
F1	0.0183 (6)	0.0291 (7)	0.0454 (8)	0.0025 (5)	0.0058 (5)	0.0017 (6)
F2	0.0519 (9)	0.0149 (6)	0.0427 (8)	−0.0093 (6)	0.0157 (6)	0.0012 (5)
F3	0.0326 (7)	0.0217 (7)	0.0823 (12)	0.0090 (6)	0.0130 (7)	0.0066 (7)
O1	0.0321 (8)	0.0254 (7)	0.0268 (7)	0.0035 (6)	0.0113 (6)	0.0000 (6)
O2	0.0283 (8)	0.0197 (7)	0.0324 (8)	−0.0045 (6)	−0.0040 (6)	−0.0075 (6)
O3	0.0186 (7)	0.0180 (6)	0.0294 (7)	−0.0040 (5)	−0.0005 (5)	−0.0066 (5)
O4	0.0183 (6)	0.0183 (6)	0.0315 (7)	−0.0028 (5)	−0.0034 (5)	0.0009 (5)
N1	0.0173 (7)	0.0143 (7)	0.0214 (7)	−0.0022 (6)	0.0010 (6)	−0.0003 (6)
C1	0.0204 (9)	0.0176 (8)	0.0167 (8)	−0.0008 (7)	0.0020 (7)	−0.0003 (6)
C2	0.0211 (9)	0.0265 (10)	0.0193 (9)	−0.0010 (8)	−0.0037 (7)	−0.0014 (7)
C3	0.0166 (9)	0.0307 (10)	0.0227 (9)	0.0035 (8)	−0.0002 (7)	0.0041 (8)
C4	0.0218 (9)	0.0185 (9)	0.0264 (9)	0.0049 (7)	0.0053 (7)	0.0044 (7)
C5	0.0194 (9)	0.0162 (8)	0.0231 (9)	−0.0016 (7)	0.0039 (7)	0.0005 (7)
C6	0.0157 (8)	0.0141 (8)	0.0173 (8)	−0.0017 (6)	0.0033 (6)	0.0014 (6)
C7	0.0158 (8)	0.0162 (8)	0.0165 (8)	−0.0013 (6)	0.0034 (6)	0.0012 (6)
C8	0.0141 (8)	0.0139 (8)	0.0283 (9)	−0.0026 (7)	−0.0016 (7)	−0.0003 (7)
C9	0.0232 (9)	0.0146 (8)	0.0257 (9)	−0.0012 (7)	0.0074 (7)	−0.0007 (7)
C10	0.0193 (9)	0.0158 (8)	0.0191 (8)	−0.0016 (7)	0.0020 (7)	0.0007 (6)
C11	0.0175 (9)	0.0219 (9)	0.0188 (8)	0.0007 (7)	0.0019 (7)	−0.0014 (7)
C12	0.0231 (9)	0.0262 (10)	0.0195 (9)	−0.0088 (8)	0.0035 (7)	−0.0021 (7)
C13	0.0352 (11)	0.0140 (8)	0.0218 (9)	−0.0066 (8)	0.0056 (8)	−0.0008 (7)
C14	0.0244 (10)	0.0178 (9)	0.0365 (11)	0.0035 (8)	0.0056 (8)	0.0022 (8)
C15	0.0179 (9)	0.0194 (9)	0.0387 (11)	−0.0026 (7)	0.0059 (8)	0.0009 (8)
C16	0.0185 (9)	0.0151 (8)	0.0220 (9)	−0.0002 (7)	0.0030 (7)	−0.0009 (7)
C17	0.0172 (8)	0.0185 (8)	0.0194 (8)	−0.0038 (7)	0.0028 (7)	−0.0011 (7)

Geometric parameters (Å, º) top

S1—O1	1.4302 (15)	C5—C6	1.401 (2)
S1—O2	1.4316 (14)	C5—H5	0.9500
S1—N1	1.6395 (16)	C6—C7	1.485 (2)
S1—C1	1.7562 (19)	C7—C16	1.347 (2)
F1—C11	1.356 (2)	C7—C8	1.530 (2)
F2—C13	1.346 (2)	C8—H8A	0.9900
F3—C14	1.352 (2)	C8—H8B	0.9900
O3—C17	1.323 (2)	C9—C10	1.509 (2)
O3—H3O	0.95 (3)	C9—H9A	0.9900
O4—C17	1.229 (2)	C9—H9B	0.9900
N1—C8	1.475 (2)	C10—C11	1.381 (3)
N1—C9	1.484 (2)	C10—C15	1.395 (3)
C1—C2	1.392 (3)	C11—C12	1.382 (3)
C1—C6	1.407 (2)	C12—C13	1.371 (3)
C2—C3	1.390 (3)	C12—H12	0.9500
C2—H2	0.9500	C13—C14	1.377 (3)
C3—C4	1.383 (3)	C14—C15	1.373 (3)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.386 (3)	C16—C17	1.468 (3)
C4—H4	0.9500	C16—H16	0.9500

O1—S1—O2	120.19 (9)	N1—C8—H8B	108.4
O1—S1—N1	107.19 (9)	C7—C8—H8B	108.4
O2—S1—N1	108.70 (9)	H8A—C8—H8B	107.5
O1—S1—C1	108.97 (9)	N1—C9—C10	111.90 (15)
O2—S1—C1	109.60 (9)	N1—C9—H9A	109.2
N1—S1—C1	100.32 (8)	C10—C9—H9A	109.2
C17—O3—H3O	104.8 (17)	N1—C9—H9B	109.2
C8—N1—C9	115.93 (15)	C10—C9—H9B	109.2
C8—N1—S1	111.38 (12)	H9A—C9—H9B	107.9
C9—N1—S1	113.89 (12)	C11—C10—C15	116.92 (17)
C2—C1—C6	122.42 (17)	C11—C10—C9	121.38 (17)
C2—C1—S1	119.82 (14)	C15—C10—C9	121.57 (17)
C6—C1—S1	117.72 (14)	F1—C11—C10	118.64 (17)
C3—C2—C1	119.01 (18)	F1—C11—C12	117.72 (17)
C3—C2—H2	120.5	C10—C11—C12	123.64 (18)
C1—C2—H2	120.5	C13—C12—C11	117.60 (18)
C4—C3—C2	119.67 (17)	C13—C12—H12	121.2
C4—C3—H3	120.2	C11—C12—H12	121.2
C2—C3—H3	120.2	F2—C13—C12	119.94 (19)
C3—C4—C5	121.01 (18)	F2—C13—C14	119.38 (19)
C3—C4—H4	119.5	C12—C13—C14	120.68 (18)
C5—C4—H4	119.5	F3—C14—C15	120.48 (19)
C4—C5—C6	121.01 (17)	F3—C14—C13	118.68 (18)
C4—C5—H5	119.5	C15—C14—C13	120.83 (19)
C6—C5—H5	119.5	C14—C15—C10	120.32 (18)
C5—C6—C1	116.76 (16)	C14—C15—H15	119.8
C5—C6—C7	121.31 (16)	C10—C15—H15	119.8
C1—C6—C7	121.89 (16)	C7—C16—C17	125.05 (17)
C16—C7—C6	119.77 (16)	C7—C16—H16	117.5
C16—C7—C8	120.87 (16)	C17—C16—H16	117.5
C6—C7—C8	119.33 (15)	O4—C17—O3	122.95 (17)
N1—C8—C7	115.47 (15)	O4—C17—C16	124.81 (16)
N1—C8—H8A	108.4	O3—C17—C16	112.24 (16)
C7—C8—H8A	108.4

O1—S1—N1—C8	−49.50 (15)	S1—N1—C8—C7	−52.72 (19)
O2—S1—N1—C8	179.16 (13)	C16—C7—C8—N1	−173.12 (17)
C1—S1—N1—C8	64.22 (14)	C6—C7—C8—N1	9.0 (2)
O1—S1—N1—C9	177.10 (12)	C8—N1—C9—C10	138.74 (16)
O2—S1—N1—C9	45.76 (15)	S1—N1—C9—C10	−90.06 (17)
C1—S1—N1—C9	−69.18 (14)	N1—C9—C10—C11	140.18 (18)
O1—S1—C1—C2	−110.27 (17)	N1—C9—C10—C15	−44.1 (2)
O2—S1—C1—C2	23.12 (19)	C15—C10—C11—F1	179.92 (17)
N1—S1—C1—C2	137.38 (16)	C9—C10—C11—F1	−4.2 (3)
O1—S1—C1—C6	71.95 (16)	C15—C10—C11—C12	−1.0 (3)
O2—S1—C1—C6	−154.67 (14)	C9—C10—C11—C12	174.89 (18)
N1—S1—C1—C6	−40.41 (16)	F1—C11—C12—C13	178.87 (16)
C6—C1—C2—C3	−2.7 (3)	C10—C11—C12—C13	−0.2 (3)
S1—C1—C2—C3	179.63 (15)	C11—C12—C13—F2	−178.12 (17)
C1—C2—C3—C4	−0.3 (3)	C11—C12—C13—C14	1.3 (3)
C2—C3—C4—C5	3.0 (3)	F2—C13—C14—F3	−0.8 (3)
C3—C4—C5—C6	−2.7 (3)	C12—C13—C14—F3	179.76 (19)
C4—C5—C6—C1	−0.3 (3)	F2—C13—C14—C15	178.26 (19)
C4—C5—C6—C7	177.32 (17)	C12—C13—C14—C15	−1.1 (3)
C2—C1—C6—C5	3.0 (3)	F3—C14—C15—C10	178.94 (19)
S1—C1—C6—C5	−179.31 (13)	C13—C14—C15—C10	−0.1 (3)
C2—C1—C6—C7	−174.62 (17)	C11—C10—C15—C14	1.2 (3)
S1—C1—C6—C7	3.1 (2)	C9—C10—C15—C14	−174.72 (19)
C5—C6—C7—C16	21.0 (3)	C6—C7—C16—C17	−178.59 (16)
C1—C6—C7—C16	−161.52 (18)	C8—C7—C16—C17	3.5 (3)
C5—C6—C7—C8	−161.05 (17)	C7—C16—C17—O4	−4.6 (3)
C1—C6—C7—C8	16.4 (3)	C7—C16—C17—O3	176.17 (17)
C9—N1—C8—C7	79.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4ⁱ	0.95 (3)	1.71 (3)	2.6454 (19)	170 (3)
C12—H12···F3ⁱⁱ	0.95	2.50	3.448 (2)	178
C15—H15···F1ⁱⁱⁱ	0.95	2.48	3.430 (2)	179
C5—H5···F2^iv	0.95	2.49	3.269 (2)	140

Symmetry codes: (i) −x, −y, −z; (ii) x+1, y, z; (iii) x−1, y, z; (iv) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4ⁱ	0.95 (3)	1.71 (3)	2.6454 (19)	170 (3)
C12—H12···F3ⁱⁱ	0.95	2.50	3.448 (2)	178.3
C15—H15···F1ⁱⁱⁱ	0.95	2.48	3.430 (2)	178.7
C5—H5···F2^iv	0.95	2.49	3.269 (2)	139.6

Symmetry codes: (i) −x, −y, −z; (ii) x+1, y, z; (iii) x−1, y, z; (iv) x, y−1, z.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 21272025), the Research Fund for the Doctoral Program of Higher Education of China (grant No. 20111101110042) and the Science and Technology Commission of Beijing (China) (grant No. Z131100004013003).

References

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-[(Z)-1,1-Dioxo-2-(2,4,5-tri­fluoro­benz­yl)-3,4-di­hydro-2H-1,2-benzo­thia­zin-4-yl­­idene]acetic acid

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Experimental

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organic compounds

2-[(Z)-1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid