2-[1,1-Dioxo-2-(2,4,5-trifluoro-benz-yl)-2H-1,2-benzothia-zin-4-yl]acetic acid.

In the title compound, C(17)H(12)F(3)NO(4)S, the heterocyclic thia-zine 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 thia-zine 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 = 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

Δρmax = 0.32 e Å−3

Δρmin = −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 ▶).

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

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

Supplementary material file. DOI: 10.1107/S1600536812015942/pv2523Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H12F3NO4S	F(000) = 784
Mr = 383.34	Dx = 1.524 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9975 reflections
a = 8.3290 (17) Å	θ = 2.5–28.4°
b = 23.141 (5) Å	µ = 0.25 mm−1
c = 8.6692 (17) Å	T = 293 K
β = 90.93 (3)°	Block, colorless
V = 1670.7 (6) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	3646 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 28.4°, θmin = 2.5°
φ and ω scans	h = −11→11
22476 measured reflections	k = −27→30
4158 independent reflections	l = −11→11

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0536P)2 + 0.5773P] where P = (Fo2 + 2Fc2)/3
4158 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.11950 (4)	0.232698 (14)	0.97865 (4)	0.03556 (11)
F1	0.69758 (14)	0.21289 (5)	0.89004 (16)	0.0722 (3)
F2	0.6328 (2)	0.02123 (6)	0.73067 (19)	0.0989 (5)
F3	0.3601 (2)	0.01403 (5)	0.8862 (2)	0.0997 (5)
O1	0.4665 (2)	0.48147 (7)	0.79699 (18)	0.0807 (5)
H1	0.504 (4)	0.5074 (14)	0.855 (3)	0.107 (10)*
O2	0.41807 (19)	0.43626 (6)	1.01497 (15)	0.0686 (4)
O3	0.08188 (15)	0.19719 (5)	1.10801 (14)	0.0526 (3)
O4	0.08941 (14)	0.20919 (5)	0.82864 (12)	0.0463 (3)
N1	0.30918 (15)	0.25127 (5)	0.99625 (14)	0.0389 (3)
C1	0.02950 (17)	0.30051 (6)	0.99039 (15)	0.0348 (3)
C2	−0.11807 (18)	0.30537 (7)	1.06150 (18)	0.0419 (3)
H2	−0.1616	0.2741	1.1136	0.050*
C3	−0.19919 (19)	0.35725 (8)	1.0537 (2)	0.0504 (4)
H3	−0.2977	0.3614	1.1014	0.060*
C4	−0.1331 (2)	0.40320 (7)	0.9744 (2)	0.0525 (4)
H4	−0.1901	0.4376	0.9658	0.063*
C5	0.0162 (2)	0.39876 (7)	0.90794 (19)	0.0453 (3)
H5	0.0589	0.4304	0.8568	0.054*
C6	0.10414 (17)	0.34714 (6)	0.91652 (15)	0.0354 (3)
C7	0.26885 (18)	0.34231 (6)	0.86404 (16)	0.0379 (3)
C8	0.36224 (18)	0.29773 (6)	0.90869 (17)	0.0387 (3)
H8	0.4691	0.2980	0.8792	0.046*
C9	0.3439 (2)	0.39103 (6)	0.77500 (19)	0.0448 (3)
H9A	0.4296	0.3755	0.7128	0.054*
H9B	0.2636	0.4074	0.7054	0.054*
C10	0.41079 (18)	0.43834 (6)	0.87590 (19)	0.0433 (3)
C11	0.4227 (2)	0.21175 (7)	1.07534 (18)	0.0448 (3)
H11A	0.3728	0.1972	1.1679	0.054*
H11B	0.5170	0.2336	1.1071	0.054*
C12	0.47589 (19)	0.16095 (7)	0.97972 (17)	0.0419 (3)
C13	0.6136 (2)	0.16311 (7)	0.8936 (2)	0.0480 (4)
C14	0.6717 (2)	0.11724 (9)	0.8094 (2)	0.0594 (4)
H14	0.7667	0.1200	0.7549	0.071*
C15	0.5833 (3)	0.06758 (8)	0.8099 (2)	0.0636 (5)
C16	0.4443 (3)	0.06386 (8)	0.8907 (3)	0.0635 (5)
C17	0.3901 (2)	0.10940 (7)	0.9768 (2)	0.0532 (4)
H17	0.2964	0.1058	1.0329	0.064*

	U11	U22	U33	U12	U13	U23
S1	0.04325 (19)	0.02765 (17)	0.03590 (18)	−0.00299 (12)	0.00411 (13)	0.00177 (12)
F1	0.0606 (7)	0.0529 (6)	0.1035 (9)	−0.0118 (5)	0.0109 (6)	−0.0096 (6)
F2	0.1302 (13)	0.0558 (8)	0.1110 (11)	0.0240 (8)	0.0069 (9)	−0.0322 (7)
F3	0.1114 (11)	0.0384 (7)	0.1489 (14)	−0.0155 (7)	−0.0099 (10)	−0.0094 (7)
O1	0.1217 (14)	0.0547 (9)	0.0655 (9)	−0.0464 (9)	−0.0027 (9)	0.0112 (7)
O2	0.0991 (11)	0.0490 (8)	0.0580 (8)	−0.0326 (7)	0.0064 (7)	−0.0001 (6)
O3	0.0639 (7)	0.0421 (6)	0.0523 (6)	−0.0011 (5)	0.0144 (5)	0.0156 (5)
O4	0.0566 (6)	0.0365 (6)	0.0457 (6)	−0.0028 (5)	−0.0032 (5)	−0.0089 (4)
N1	0.0412 (6)	0.0332 (6)	0.0424 (6)	−0.0001 (5)	−0.0004 (5)	0.0018 (5)
C1	0.0411 (7)	0.0302 (6)	0.0331 (6)	−0.0014 (5)	0.0012 (5)	−0.0017 (5)
C2	0.0420 (7)	0.0416 (8)	0.0423 (7)	−0.0052 (6)	0.0048 (6)	0.0002 (6)
C3	0.0416 (8)	0.0525 (9)	0.0573 (9)	0.0042 (7)	0.0078 (7)	−0.0013 (7)
C4	0.0495 (9)	0.0419 (9)	0.0662 (10)	0.0100 (7)	0.0044 (7)	0.0025 (7)
C5	0.0517 (8)	0.0329 (7)	0.0514 (8)	0.0015 (6)	0.0044 (7)	0.0037 (6)
C6	0.0423 (7)	0.0295 (7)	0.0344 (6)	−0.0023 (5)	0.0020 (5)	−0.0015 (5)
C7	0.0459 (7)	0.0279 (6)	0.0402 (7)	−0.0049 (5)	0.0085 (6)	−0.0032 (5)
C8	0.0403 (7)	0.0327 (7)	0.0434 (7)	−0.0047 (5)	0.0063 (6)	−0.0041 (5)
C9	0.0538 (8)	0.0320 (7)	0.0491 (8)	−0.0048 (6)	0.0167 (7)	−0.0006 (6)
C10	0.0424 (7)	0.0308 (7)	0.0572 (9)	−0.0036 (6)	0.0103 (6)	0.0024 (6)
C11	0.0513 (8)	0.0433 (8)	0.0394 (7)	0.0062 (7)	−0.0103 (6)	−0.0030 (6)
C12	0.0484 (8)	0.0356 (7)	0.0413 (7)	0.0047 (6)	−0.0097 (6)	0.0019 (6)
C13	0.0512 (8)	0.0382 (8)	0.0543 (9)	0.0021 (6)	−0.0063 (7)	−0.0013 (7)
C14	0.0631 (11)	0.0552 (11)	0.0601 (11)	0.0133 (9)	0.0033 (8)	−0.0029 (8)
C15	0.0838 (13)	0.0409 (9)	0.0659 (11)	0.0163 (9)	−0.0075 (10)	−0.0110 (8)
C16	0.0782 (13)	0.0320 (8)	0.0796 (13)	−0.0022 (8)	−0.0153 (10)	−0.0013 (8)
C17	0.0579 (10)	0.0395 (8)	0.0621 (10)	0.0000 (7)	−0.0032 (8)	0.0049 (7)

S1—O4	1.4281 (11)	C5—C6	1.403 (2)
S1—O3	1.4292 (11)	C5—H5	0.9300
S1—N1	1.6420 (13)	C6—C7	1.457 (2)
S1—C1	1.7427 (14)	C7—C8	1.345 (2)
F1—C13	1.348 (2)	C7—C9	1.5076 (19)
F2—C15	1.342 (2)	C8—H8	0.9300
F3—C16	1.350 (2)	C9—C10	1.503 (2)
O1—C10	1.2998 (19)	C9—H9A	0.9700
O1—H1	0.84 (3)	C9—H9B	0.9700
O2—C10	1.207 (2)	C11—C12	1.509 (2)
N1—C8	1.3923 (18)	C11—H11A	0.9700
N1—C11	1.4765 (19)	C11—H11B	0.9700
C1—C2	1.388 (2)	C12—C13	1.379 (2)
C1—C6	1.4049 (19)	C12—C17	1.391 (2)
C2—C3	1.379 (2)	C13—C14	1.380 (2)
C2—H2	0.9300	C14—C15	1.365 (3)
C3—C4	1.385 (2)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.366 (3)
C4—C5	1.383 (2)	C16—C17	1.372 (3)
C4—H4	0.9300	C17—H17	0.9300
O4—S1—O3	117.26 (8)	C10—C9—C7	113.55 (13)
O4—S1—N1	109.80 (7)	C10—C9—H9A	108.9
O3—S1—N1	107.48 (8)	C7—C9—H9A	108.9
O4—S1—C1	109.08 (7)	C10—C9—H9B	108.9
O3—S1—C1	111.83 (7)	C7—C9—H9B	108.9
N1—S1—C1	99.97 (7)	H9A—C9—H9B	107.7
C10—O1—H1	111 (2)	O2—C10—O1	122.93 (16)
C8—N1—C11	121.67 (13)	O2—C10—C9	124.36 (14)
C8—N1—S1	117.70 (10)	O1—C10—C9	112.65 (15)
C11—N1—S1	119.28 (11)	N1—C11—C12	114.76 (12)
C2—C1—C6	122.78 (13)	N1—C11—H11A	108.6
C2—C1—S1	118.92 (11)	C12—C11—H11A	108.6
C6—C1—S1	118.10 (10)	N1—C11—H11B	108.6
C3—C2—C1	119.04 (14)	C12—C11—H11B	108.6
C3—C2—H2	120.5	H11A—C11—H11B	107.6
C1—C2—H2	120.5	C13—C12—C17	116.91 (15)
C2—C3—C4	119.63 (15)	C13—C12—C11	121.54 (14)
C2—C3—H3	120.2	C17—C12—C11	121.54 (15)
C4—C3—H3	120.2	F1—C13—C12	118.65 (15)
C5—C4—C3	121.14 (15)	F1—C13—C14	117.28 (16)
C5—C4—H4	119.4	C12—C13—C14	124.07 (16)
C3—C4—H4	119.4	C15—C14—C13	116.87 (18)
C4—C5—C6	120.89 (14)	C15—C14—H14	121.6
C4—C5—H5	119.6	C13—C14—H14	121.6
C6—C5—H5	119.6	F2—C15—C14	120.1 (2)
C5—C6—C1	116.36 (13)	F2—C15—C16	118.81 (19)
C5—C6—C7	122.84 (13)	C14—C15—C16	121.11 (17)
C1—C6—C7	120.62 (13)	F3—C16—C15	118.92 (19)
C8—C7—C6	120.81 (13)	F3—C16—C17	119.8 (2)
C8—C7—C9	118.58 (13)	C15—C16—C17	121.31 (17)
C6—C7—C9	120.18 (13)	C16—C17—C12	119.69 (18)
C7—C8—N1	124.19 (13)	C16—C17—H17	120.2
C7—C8—H8	117.9	C12—C17—H17	120.2
N1—C8—H8	117.9

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—H11A···O3	0.97	2.47	2.877 (2)	105
C11—H11B···F1	0.97	2.47	2.818 (2)	101
C11—H11B···O4iii	0.97	2.40	3.162 (2)	135

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

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