[2-(2,5-Dichloro-benz-yl)-4-hy-droxy-1,1-dioxo-2H-1,2-benzothia-zin-3-yl](phen-yl)methanone.

In the title mol-ecule, C(22)H(15)Cl(2)NO(4)S, the heterocyclic thia-zine ring adopts a half-chair conformation, with the S and N atoms displaced by 0.343 (5) and 0.402 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The mol-ecular structure is consolidated by an intra-molecular O-H⋯O hydrogen bond, which generates an S(?) ring. In the crystal, the molecules are linked by C-H⋯O interactions into [010] chains.

Related literature

For background information on the activity of anti-inflammatory and analgesic oxicams, see: Lombardino et al. (1971 ▶); Soler (1985 ▶); Carty et al. (1993 ▶); Turck et al. (1995 ▶); Blackham & Owen (1975 ▶). For the biological activity of benzothia­zine derivatives, see: Zia-ur-Rehman et al. (2005 ▶); Ahmad et al. (2010 ▶). For the syntheses and crystal stuctures of related benzothia­zine derivatives, see: Ahmad et al. (2011 ▶); Aslam et al. (2012 ▶).

Experimental

Crystal data

C22H15Cl2NO4S

M = 460.32

Monoclinic,

a = 12.8172 (5) Å

b = 9.9215 (4) Å

c = 16.7155 (5) Å

β = 110.511 (2)°

V = 1990.89 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 173 K

0.20 × 0.18 × 0.16 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.913, T max = 0.930

16108 measured reflections

4592 independent reflections

3598 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.118

S = 1.11

4592 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.44 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201481X/rk2344sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201481X/rk2344Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201481X/rk2344Isup3.cml

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

C22H15Cl2NO4S	F(000) = 944
Mr = 460.32	Dx = 1.536 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8696 reflections
a = 12.8172 (5) Å	θ = 1.0–27.5°
b = 9.9215 (4) Å	µ = 0.46 mm−1
c = 16.7155 (5) Å	T = 173 K
β = 110.511 (2)°	Prism, yellow
V = 1990.89 (13) Å3	0.20 × 0.18 × 0.16 mm
Z = 4

Nonius KappaCCD diffractometer	4592 independent reflections
Radiation source: fine-focus sealed tube	3598 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
ω and φ scans	θmax = 27.6°, θmin = 2.7°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −16→16
Tmin = 0.913, Tmax = 0.930	k = −12→12
16108 measured reflections	l = −21→20

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0232P)2 + 2.3517P] where P = (Fo2 + 2Fc2)/3
4592 reflections	(Δ/σ)max = 0.001
272 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Cl1	0.52481 (7)	−0.04749 (10)	0.39033 (6)	0.0658 (3)
Cl2	0.50174 (9)	0.57915 (12)	0.37257 (7)	0.0804 (3)
S1	0.87675 (5)	0.25684 (7)	0.53887 (4)	0.03478 (16)
O1	0.98780 (15)	0.2067 (2)	0.56375 (12)	0.0457 (5)
O2	0.84712 (17)	0.3467 (2)	0.59407 (11)	0.0465 (5)
O3	0.79566 (17)	0.0186 (2)	0.31269 (11)	0.0418 (5)
H3O	0.7866	−0.0624	0.3235	0.050*
O4	0.77251 (15)	−0.18006 (19)	0.40080 (11)	0.0408 (5)
N1	0.79342 (17)	0.1262 (2)	0.52149 (12)	0.0331 (5)
C1	0.8421 (2)	0.3280 (3)	0.43643 (16)	0.0339 (6)
C2	0.8521 (2)	0.4653 (3)	0.42629 (18)	0.0406 (6)
H2	0.8739	0.5236	0.4744	0.049*
C3	0.8297 (2)	0.5165 (3)	0.34482 (19)	0.0465 (7)
H3	0.8365	0.6104	0.3369	0.056*
C4	0.7977 (3)	0.4316 (3)	0.27565 (18)	0.0483 (7)
H4	0.7830	0.4676	0.2201	0.058*
C5	0.7866 (2)	0.2949 (3)	0.28534 (17)	0.0421 (7)
H5	0.7638	0.2378	0.2366	0.050*
C6	0.8089 (2)	0.2404 (3)	0.36662 (15)	0.0318 (5)
C7	0.7989 (2)	0.0952 (3)	0.37903 (15)	0.0326 (6)
C8	0.7978 (2)	0.0396 (3)	0.45361 (14)	0.0307 (5)
C9	0.7971 (2)	−0.1051 (3)	0.46462 (16)	0.0334 (6)
C10	0.8276 (2)	−0.1656 (3)	0.55114 (16)	0.0357 (6)
C11	0.9160 (2)	−0.1140 (3)	0.61913 (17)	0.0403 (6)
H11	0.9531	−0.0345	0.6119	0.048*
C12	0.9498 (2)	−0.1792 (3)	0.69745 (18)	0.0463 (7)
H12	1.0107	−0.1448	0.7438	0.056*
C13	0.8954 (3)	−0.2934 (3)	0.70810 (19)	0.0498 (8)
H13	0.9190	−0.3376	0.7619	0.060*
C14	0.8066 (3)	−0.3445 (3)	0.6410 (2)	0.0505 (8)
H14	0.7685	−0.4226	0.6491	0.061*
C15	0.7735 (3)	−0.2815 (3)	0.56220 (19)	0.0448 (7)
H15	0.7137	−0.3175	0.5157	0.054*
C16	0.6823 (2)	0.1408 (3)	0.53043 (16)	0.0376 (6)
H16A	0.6906	0.1968	0.5813	0.045*
H16B	0.6560	0.0507	0.5403	0.045*
C17	0.5954 (2)	0.2036 (3)	0.45391 (16)	0.0396 (6)
C18	0.5232 (2)	0.1274 (4)	0.38632 (19)	0.0502 (8)
C19	0.4486 (3)	0.1900 (5)	0.3150 (2)	0.0661 (11)
H19	0.4009	0.1372	0.2695	0.079*
C20	0.4435 (3)	0.3273 (5)	0.3101 (2)	0.0685 (11)
H20	0.3933	0.3699	0.2606	0.082*
C21	0.5114 (3)	0.4044 (4)	0.37701 (19)	0.0564 (9)
C22	0.5870 (2)	0.3432 (3)	0.44836 (17)	0.0437 (7)
H22	0.6336	0.3972	0.4938	0.052*

	U11	U22	U33	U12	U13	U23
Cl1	0.0454 (4)	0.0807 (7)	0.0762 (6)	−0.0194 (4)	0.0274 (4)	−0.0311 (5)
Cl2	0.0780 (7)	0.0882 (8)	0.0780 (6)	0.0331 (6)	0.0310 (5)	0.0324 (6)
S1	0.0355 (3)	0.0382 (4)	0.0259 (3)	−0.0025 (3)	0.0048 (2)	−0.0050 (3)
O1	0.0316 (10)	0.0547 (13)	0.0402 (10)	−0.0033 (9)	−0.0006 (8)	−0.0019 (9)
O2	0.0582 (13)	0.0452 (12)	0.0332 (10)	−0.0025 (10)	0.0124 (9)	−0.0114 (9)
O3	0.0569 (12)	0.0388 (11)	0.0303 (9)	−0.0066 (10)	0.0160 (9)	−0.0086 (8)
O4	0.0440 (11)	0.0395 (11)	0.0358 (10)	−0.0041 (9)	0.0102 (8)	−0.0087 (8)
N1	0.0342 (11)	0.0379 (12)	0.0265 (10)	−0.0022 (10)	0.0100 (9)	−0.0041 (9)
C1	0.0311 (13)	0.0375 (15)	0.0310 (13)	−0.0010 (11)	0.0082 (10)	−0.0024 (11)
C2	0.0414 (15)	0.0378 (15)	0.0399 (15)	−0.0015 (12)	0.0108 (12)	−0.0062 (12)
C3	0.0529 (18)	0.0349 (16)	0.0515 (17)	0.0000 (13)	0.0178 (14)	0.0047 (13)
C4	0.0578 (19)	0.0464 (18)	0.0389 (15)	−0.0002 (15)	0.0146 (14)	0.0081 (13)
C5	0.0469 (16)	0.0474 (17)	0.0304 (13)	−0.0005 (13)	0.0117 (12)	−0.0024 (12)
C6	0.0305 (12)	0.0366 (14)	0.0276 (11)	−0.0021 (11)	0.0092 (10)	−0.0020 (11)
C7	0.0281 (12)	0.0398 (15)	0.0290 (12)	−0.0016 (11)	0.0088 (10)	−0.0074 (11)
C8	0.0276 (12)	0.0380 (14)	0.0246 (11)	−0.0008 (11)	0.0066 (9)	−0.0035 (10)
C9	0.0274 (12)	0.0388 (15)	0.0337 (13)	−0.0021 (11)	0.0103 (10)	−0.0028 (11)
C10	0.0379 (14)	0.0354 (14)	0.0349 (13)	0.0042 (12)	0.0140 (11)	0.0028 (11)
C11	0.0391 (15)	0.0417 (16)	0.0387 (14)	0.0041 (12)	0.0119 (12)	0.0034 (12)
C12	0.0454 (16)	0.0536 (19)	0.0365 (15)	0.0096 (14)	0.0102 (13)	0.0026 (13)
C13	0.062 (2)	0.0496 (19)	0.0413 (16)	0.0147 (16)	0.0226 (15)	0.0116 (14)
C14	0.067 (2)	0.0375 (17)	0.0579 (19)	0.0017 (15)	0.0351 (17)	0.0071 (14)
C15	0.0504 (17)	0.0423 (17)	0.0449 (16)	−0.0002 (13)	0.0206 (14)	−0.0016 (13)
C16	0.0365 (14)	0.0490 (17)	0.0306 (13)	−0.0006 (12)	0.0156 (11)	−0.0037 (12)
C17	0.0292 (13)	0.0628 (19)	0.0296 (13)	0.0001 (13)	0.0138 (11)	−0.0029 (12)
C18	0.0313 (14)	0.079 (2)	0.0444 (16)	−0.0037 (15)	0.0190 (13)	−0.0138 (16)
C19	0.0351 (17)	0.119 (4)	0.0399 (18)	−0.002 (2)	0.0073 (14)	−0.013 (2)
C20	0.0389 (18)	0.124 (4)	0.0366 (17)	0.018 (2)	0.0057 (14)	0.015 (2)
C21	0.0395 (16)	0.088 (3)	0.0434 (17)	0.0170 (17)	0.0171 (14)	0.0127 (17)
C22	0.0343 (14)	0.065 (2)	0.0340 (14)	0.0068 (14)	0.0142 (12)	0.0029 (13)

Cl1—C18	1.736 (4)	C9—C10	1.486 (3)
Cl2—C21	1.738 (4)	C10—C15	1.389 (4)
S1—O1	1.425 (2)	C10—C11	1.391 (4)
S1—O2	1.4268 (19)	C11—C12	1.386 (4)
S1—N1	1.640 (2)	C11—H11	0.9500
S1—C1	1.759 (3)	C12—C13	1.375 (4)
O3—C7	1.333 (3)	C12—H12	0.9500
O3—H3O	0.8400	C13—C14	1.384 (4)
O4—C9	1.247 (3)	C13—H13	0.9500
N1—C8	1.440 (3)	C14—C15	1.384 (4)
N1—C16	1.491 (3)	C14—H14	0.9500
C1—C2	1.384 (4)	C15—H15	0.9500
C1—C6	1.397 (3)	C16—C17	1.506 (4)
C2—C3	1.386 (4)	C16—H16A	0.9900
C2—H2	0.9500	C16—H16B	0.9900
C3—C4	1.372 (4)	C17—C22	1.389 (4)
C3—H3	0.9500	C17—C18	1.404 (4)
C4—C5	1.379 (4)	C18—C19	1.387 (5)
C4—H4	0.9500	C19—C20	1.365 (6)
C5—C6	1.396 (4)	C19—H19	0.9500
C5—H5	0.9500	C20—C21	1.383 (5)
C6—C7	1.467 (4)	C20—H20	0.9500
C7—C8	1.368 (3)	C21—C22	1.386 (4)
C8—C9	1.448 (4)	C22—H22	0.9500
O1—S1—O2	119.62 (12)	C12—C11—C10	119.7 (3)
O1—S1—N1	107.33 (12)	C12—C11—H11	120.1
O2—S1—N1	107.70 (12)	C10—C11—H11	120.1
O1—S1—C1	108.03 (12)	C13—C12—C11	120.1 (3)
O2—S1—C1	110.19 (12)	C13—C12—H12	119.9
N1—S1—C1	102.62 (11)	C11—C12—H12	119.9
C7—O3—H3O	109.5	C12—C13—C14	120.5 (3)
C8—N1—C16	116.06 (19)	C12—C13—H13	119.7
C8—N1—S1	114.13 (16)	C14—C13—H13	119.7
C16—N1—S1	119.42 (18)	C13—C14—C15	119.8 (3)
C2—C1—C6	121.6 (2)	C13—C14—H14	120.1
C2—C1—S1	120.8 (2)	C15—C14—H14	120.1
C6—C1—S1	117.5 (2)	C14—C15—C10	120.0 (3)
C1—C2—C3	119.0 (3)	C14—C15—H15	120.0
C1—C2—H2	120.5	C10—C15—H15	120.0
C3—C2—H2	120.5	N1—C16—C17	113.8 (2)
C4—C3—C2	120.1 (3)	N1—C16—H16A	108.8
C4—C3—H3	120.0	C17—C16—H16A	108.8
C2—C3—H3	120.0	N1—C16—H16B	108.8
C3—C4—C5	121.2 (3)	C17—C16—H16B	108.8
C3—C4—H4	119.4	H16A—C16—H16B	107.7
C5—C4—H4	119.4	C22—C17—C18	118.0 (3)
C4—C5—C6	120.1 (3)	C22—C17—C16	119.1 (3)
C4—C5—H5	120.0	C18—C17—C16	122.9 (3)
C6—C5—H5	120.0	C19—C18—C17	120.7 (3)
C5—C6—C1	118.1 (2)	C19—C18—Cl1	118.4 (3)
C5—C6—C7	121.3 (2)	C17—C18—Cl1	120.8 (3)
C1—C6—C7	120.6 (2)	C20—C19—C18	120.3 (3)
O3—C7—C8	121.4 (2)	C20—C19—H19	119.9
O3—C7—C6	114.9 (2)	C18—C19—H19	119.9
C8—C7—C6	123.7 (2)	C19—C20—C21	119.9 (3)
C7—C8—N1	119.5 (2)	C19—C20—H20	120.0
C7—C8—C9	121.2 (2)	C21—C20—H20	120.0
N1—C8—C9	119.2 (2)	C20—C21—C22	120.4 (4)
O4—C9—C8	119.6 (2)	C20—C21—Cl2	120.1 (3)
O4—C9—C10	119.6 (2)	C22—C21—Cl2	119.4 (3)
C8—C9—C10	120.8 (2)	C21—C22—C17	120.5 (3)
C15—C10—C11	119.9 (3)	C21—C22—H22	119.7
C15—C10—C9	119.4 (2)	C17—C22—H22	119.7
C11—C10—C9	120.5 (2)
O1—S1—N1—C8	−61.89 (19)	S1—N1—C8—C9	138.3 (2)
O2—S1—N1—C8	168.09 (17)	C7—C8—C9—O4	−16.1 (4)
C1—S1—N1—C8	51.8 (2)	N1—C8—C9—O4	161.9 (2)
O1—S1—N1—C16	154.46 (18)	C7—C8—C9—C10	162.6 (2)
O2—S1—N1—C16	24.5 (2)	N1—C8—C9—C10	−19.5 (3)
C1—S1—N1—C16	−91.83 (19)	O4—C9—C10—C15	−36.4 (4)
O1—S1—C1—C2	−96.7 (2)	C8—C9—C10—C15	144.9 (3)
O2—S1—C1—C2	35.6 (3)	O4—C9—C10—C11	138.0 (3)
N1—S1—C1—C2	150.1 (2)	C8—C9—C10—C11	−40.7 (4)
O1—S1—C1—C6	80.8 (2)	C15—C10—C11—C12	0.3 (4)
O2—S1—C1—C6	−146.9 (2)	C9—C10—C11—C12	−174.1 (3)
N1—S1—C1—C6	−32.4 (2)	C10—C11—C12—C13	−0.7 (4)
C6—C1—C2—C3	−0.8 (4)	C11—C12—C13—C14	0.0 (4)
S1—C1—C2—C3	176.6 (2)	C12—C13—C14—C15	1.1 (5)
C1—C2—C3—C4	0.3 (4)	C13—C14—C15—C10	−1.5 (4)
C2—C3—C4—C5	0.3 (5)	C11—C10—C15—C14	0.8 (4)
C3—C4—C5—C6	−0.5 (5)	C9—C10—C15—C14	175.3 (3)
C4—C5—C6—C1	0.0 (4)	C8—N1—C16—C17	−62.6 (3)
C4—C5—C6—C7	−179.3 (3)	S1—N1—C16—C17	80.4 (3)
C2—C1—C6—C5	0.7 (4)	N1—C16—C17—C22	−86.3 (3)
S1—C1—C6—C5	−176.8 (2)	N1—C16—C17—C18	92.3 (3)
C2—C1—C6—C7	−180.0 (2)	C22—C17—C18—C19	2.1 (4)
S1—C1—C6—C7	2.5 (3)	C16—C17—C18—C19	−176.5 (3)
C5—C6—C7—O3	16.2 (4)	C22—C17—C18—Cl1	−177.5 (2)
C1—C6—C7—O3	−163.1 (2)	C16—C17—C18—Cl1	3.9 (4)
C5—C6—C7—C8	−166.5 (2)	C17—C18—C19—C20	−0.7 (5)
C1—C6—C7—C8	14.2 (4)	Cl1—C18—C19—C20	178.9 (3)
O3—C7—C8—N1	−175.6 (2)	C18—C19—C20—C21	−1.2 (5)
C6—C7—C8—N1	7.3 (4)	C19—C20—C21—C22	1.8 (5)
O3—C7—C8—C9	2.3 (4)	C19—C20—C21—Cl2	−177.8 (3)
C6—C7—C8—C9	−174.8 (2)	C20—C21—C22—C17	−0.4 (4)
C16—N1—C8—C7	101.2 (3)	Cl2—C21—C22—C17	179.2 (2)
S1—N1—C8—C7	−43.8 (3)	C18—C17—C22—C21	−1.5 (4)
C16—N1—C8—C9	−76.8 (3)	C16—C17—C22—C21	177.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4i	0.95	2.60	3.310 (4)	132
O3—H3O···O4	0.84	1.80	2.539 (3)	146
C11—H11···N1	0.95	2.62	3.003 (3)	105
C16—H16A···O2	0.99	2.45	2.862 (3)	105
C16—H16B···Cl1	0.99	2.67	3.120 (3)	108

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O4i	0.95	2.60	3.310 (4)	132
O3—H3O⋯O4	0.84	1.80	2.539 (3)	146

Symmetry code: (i) .