2-[(Z)-1,1-Dioxo-2-(2,4,5-tri-fluoro-benz-yl)-3,4-di-hydro-2H-1,2-benzo-thia-zin-4-yl-idene]acetic acid.

In the title compound, C17H12F3NO4S, the heterocyclic thia-zine 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 benzo-thia-zine moiety. In the crystal, inversion dimers linked by pairs of carb-oxy-lic acid O-H⋯O hydrogen bonds generate R 2 (2)(8) loops. Each of the F atoms accepts a Ca-H⋯F (a = aromatic) hydrogen bond from an adjacent mol-ecule, resulting in (001) sheets.

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 = 383.34

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.130

S = 1.00

4123 reflections

239 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.46 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814008903/zs2294sup1.cif

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

Click here for additional data file.

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

Click here for additional data file.

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

CCDC reference: 998389

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H12F3NO4S	F(000) = 784
Mr = 383.34	Dx = 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

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

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(Fo2) + (0.0691P)2 + 0.960P] where P = (Fo2 + 2Fc2)/3
4123 reflections	(Δ/σ)max = 0.001
239 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···F2iv	0.95	2.49	3.269 (2)	140

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⋯F2iv	0.95	2.49	3.269 (2)	140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .