(2-Chloro-phen-yl)(4-hy-droxy-1,1-dioxo-2H-1,2-benzothia-zin-3-yl)methanone.

In the title mol-ecule, C(15)H(10)ClNO(4)S, the heterocyclic thia-zine ring adopts a half-chair conformation, with the S and N atoms displaced by 0.527 (7) and 0.216 (7) 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 inter-action and the crystal packing is stabilized by N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For background information on the synthesis of related compounds, see: Siddiqui et al. (2007 ▶). For the biological activity of 1,2-benzothia­zine derivatives, see: Ikeda et al. (1992 ▶); Lombardino et al. (1973 ▶); Gupta et al. (2002 ▶); Zia-ur-Rehman et al. (2006 ▶); Ahmad et al. (2010 ▶). For bromo analogue of the title compound, see: Sattar et al. (2012 ▶).

Experimental

Crystal data

C15H10ClNO4S

M = 335.75

Monoclinic,

a = 12.1078 (6) Å

b = 8.4057 (5) Å

c = 14.7022 (9) Å

β = 105.541 (3)°

V = 1441.60 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 173 K

0.12 × 0.10 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.951, T max = 0.975

5606 measured reflections

3204 independent reflections

2383 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.138

S = 1.12

3204 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.36 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812014171/zj2065sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014171/zj2065Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014171/zj2065Isup3.cml

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

C15H10ClNO4S	F(000) = 688
Mr = 335.75	Dx = 1.547 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2930 reflections
a = 12.1078 (6) Å	θ = 1.0–27.5°
b = 8.4057 (5) Å	µ = 0.43 mm−1
c = 14.7022 (9) Å	T = 173 K
β = 105.541 (3)°	Prism, pale yellow
V = 1441.60 (14) Å3	0.12 × 0.10 × 0.06 mm
Z = 4

Nonius KappaCCD diffractometer	3204 independent reflections
Radiation source: fine-focus sealed tube	2383 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
ω and φ scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −15→15
Tmin = 0.951, Tmax = 0.975	k = −10→10
5606 measured reflections	l = −19→19

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + 4.364P] where P = (Fo2 + 2Fc2)/3
3204 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.36 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
Cl1	0.71096 (9)	0.38782 (15)	0.83022 (8)	0.0469 (3)
S1	0.18808 (7)	0.39935 (12)	0.60671 (6)	0.0281 (2)
O1	0.1528 (2)	0.2392 (3)	0.58127 (18)	0.0358 (7)
O2	0.1631 (2)	0.5208 (4)	0.53640 (19)	0.0396 (7)
O3	0.3300 (2)	0.2131 (3)	0.88114 (18)	0.0340 (6)
H3O	0.3920	0.1661	0.8837	0.041*
O4	0.5099 (2)	0.1471 (3)	0.83156 (18)	0.0341 (6)
N1	0.3252 (2)	0.3988 (4)	0.6544 (2)	0.0278 (7)
H1N	0.358 (3)	0.487 (5)	0.655 (3)	0.033*
C1	0.1348 (3)	0.4509 (5)	0.7026 (3)	0.0273 (8)
C2	0.0344 (3)	0.5377 (5)	0.6909 (3)	0.0386 (10)
H2	−0.0038	0.5812	0.6312	0.046*
C3	−0.0087 (4)	0.5595 (5)	0.7679 (3)	0.0411 (10)
H3	−0.0778	0.6179	0.7605	0.049*
C4	0.0460 (3)	0.4985 (5)	0.8555 (3)	0.0386 (10)
H4	0.0147	0.5155	0.9074	0.046*
C5	0.1461 (3)	0.4128 (5)	0.8679 (3)	0.0318 (8)
H5	0.1832	0.3699	0.9281	0.038*
C6	0.1931 (3)	0.3892 (4)	0.7913 (2)	0.0249 (7)
C7	0.3004 (3)	0.3016 (4)	0.8035 (2)	0.0253 (7)
C8	0.3659 (3)	0.3096 (4)	0.7403 (2)	0.0250 (7)
C9	0.4744 (3)	0.2291 (5)	0.7586 (3)	0.0284 (8)
C10	0.5468 (3)	0.2430 (4)	0.6910 (3)	0.0265 (8)
C11	0.6580 (3)	0.3042 (5)	0.7190 (3)	0.0300 (8)
C12	0.7263 (4)	0.3083 (5)	0.6570 (3)	0.0406 (10)
H12	0.8011	0.3525	0.6765	0.049*
C13	0.6856 (4)	0.2483 (5)	0.5672 (3)	0.0406 (10)
H13	0.7326	0.2502	0.5248	0.049*
C14	0.5764 (4)	0.1854 (5)	0.5387 (3)	0.0391 (10)
H14	0.5490	0.1417	0.4772	0.047*
C15	0.5063 (3)	0.1858 (5)	0.5996 (3)	0.0349 (9)
H15	0.4301	0.1465	0.5785	0.042*

	U11	U22	U33	U12	U13	U23
Cl1	0.0364 (5)	0.0581 (7)	0.0450 (6)	−0.0087 (5)	0.0087 (4)	−0.0126 (5)
S1	0.0242 (4)	0.0341 (5)	0.0262 (4)	−0.0017 (4)	0.0072 (3)	0.0021 (4)
O1	0.0359 (14)	0.0401 (16)	0.0324 (14)	−0.0094 (13)	0.0109 (11)	−0.0065 (13)
O2	0.0331 (14)	0.0514 (19)	0.0334 (15)	0.0028 (14)	0.0073 (12)	0.0157 (14)
O3	0.0298 (14)	0.0426 (17)	0.0314 (14)	0.0113 (13)	0.0112 (11)	0.0104 (13)
O4	0.0292 (13)	0.0410 (17)	0.0329 (14)	0.0093 (12)	0.0096 (11)	0.0062 (13)
N1	0.0233 (15)	0.0292 (17)	0.0328 (17)	−0.0023 (14)	0.0106 (13)	0.0036 (14)
C1	0.0260 (17)	0.028 (2)	0.0296 (18)	−0.0022 (15)	0.0096 (14)	0.0008 (16)
C2	0.032 (2)	0.042 (2)	0.041 (2)	0.0089 (19)	0.0087 (17)	0.007 (2)
C3	0.034 (2)	0.039 (2)	0.054 (3)	0.0106 (19)	0.0177 (19)	0.000 (2)
C4	0.037 (2)	0.043 (2)	0.044 (2)	0.0059 (19)	0.0248 (19)	0.000 (2)
C5	0.0342 (19)	0.035 (2)	0.0291 (19)	0.0018 (18)	0.0140 (16)	0.0007 (17)
C6	0.0235 (16)	0.0253 (18)	0.0263 (17)	−0.0032 (15)	0.0075 (14)	−0.0001 (15)
C7	0.0248 (17)	0.0252 (19)	0.0257 (17)	0.0006 (15)	0.0067 (14)	0.0005 (15)
C8	0.0217 (16)	0.0281 (19)	0.0254 (17)	−0.0016 (15)	0.0063 (13)	0.0006 (15)
C9	0.0262 (18)	0.031 (2)	0.0279 (18)	−0.0024 (16)	0.0077 (14)	−0.0055 (16)
C10	0.0248 (17)	0.0269 (19)	0.0306 (18)	0.0054 (15)	0.0124 (14)	0.0016 (15)
C11	0.0272 (18)	0.027 (2)	0.037 (2)	0.0015 (16)	0.0111 (16)	0.0030 (16)
C12	0.033 (2)	0.039 (2)	0.055 (3)	0.0013 (19)	0.021 (2)	0.004 (2)
C13	0.047 (2)	0.040 (2)	0.043 (2)	0.008 (2)	0.027 (2)	0.008 (2)
C14	0.041 (2)	0.044 (3)	0.034 (2)	0.007 (2)	0.0143 (18)	0.0022 (19)
C15	0.031 (2)	0.042 (2)	0.033 (2)	0.0027 (18)	0.0104 (16)	0.0012 (18)

Cl1—C11	1.737 (4)	C4—H4	0.9500
S1—O2	1.427 (3)	C5—C6	1.404 (5)
S1—O1	1.431 (3)	C5—H5	0.9500
S1—N1	1.620 (3)	C6—C7	1.462 (5)
S1—C1	1.755 (4)	C7—C8	1.376 (5)
O3—C7	1.329 (4)	C8—C9	1.438 (5)
O3—H3O	0.8400	C9—C10	1.497 (5)
O4—C9	1.250 (4)	C10—C15	1.387 (5)
N1—C8	1.437 (5)	C10—C11	1.395 (5)
N1—H1N	0.84 (4)	C11—C12	1.386 (5)
C1—C2	1.388 (5)	C12—C13	1.375 (6)
C1—C6	1.405 (5)	C12—H12	0.9500
C2—C3	1.380 (6)	C13—C14	1.381 (6)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.379 (6)	C14—C15	1.388 (5)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.379 (5)	C15—H15	0.9500
O2—S1—O1	119.57 (18)	O3—C7—C8	122.4 (3)
O2—S1—N1	108.01 (17)	O3—C7—C6	114.4 (3)
O1—S1—N1	108.05 (18)	C8—C7—C6	123.2 (3)
O2—S1—C1	110.69 (18)	C7—C8—N1	119.7 (3)
O1—S1—C1	107.08 (17)	C7—C8—C9	120.9 (3)
N1—S1—C1	102.01 (17)	N1—C8—C9	119.4 (3)
C7—O3—H3O	109.5	O4—C9—C8	120.5 (3)
C8—N1—S1	116.8 (2)	O4—C9—C10	119.1 (3)
C8—N1—H1N	114 (3)	C8—C9—C10	120.4 (3)
S1—N1—H1N	115 (3)	C15—C10—C11	118.5 (3)
C2—C1—C6	121.0 (3)	C15—C10—C9	119.9 (3)
C2—C1—S1	121.9 (3)	C11—C10—C9	121.5 (3)
C6—C1—S1	116.9 (3)	C12—C11—C10	120.9 (4)
C3—C2—C1	118.6 (4)	C12—C11—Cl1	118.3 (3)
C3—C2—H2	120.7	C10—C11—Cl1	120.7 (3)
C1—C2—H2	120.7	C13—C12—C11	119.9 (4)
C4—C3—C2	121.5 (4)	C13—C12—H12	120.0
C4—C3—H3	119.2	C11—C12—H12	120.0
C2—C3—H3	119.2	C12—C13—C14	120.0 (4)
C5—C4—C3	120.2 (4)	C12—C13—H13	120.0
C5—C4—H4	119.9	C14—C13—H13	120.0
C3—C4—H4	119.9	C13—C14—C15	120.3 (4)
C4—C5—C6	119.9 (4)	C13—C14—H14	119.9
C4—C5—H5	120.0	C15—C14—H14	119.9
C6—C5—H5	120.0	C10—C15—C14	120.4 (4)
C5—C6—C1	118.7 (3)	C10—C15—H15	119.8
C5—C6—C7	120.8 (3)	C14—C15—H15	119.8
C1—C6—C7	120.5 (3)
O2—S1—N1—C8	166.9 (3)	C6—C7—C8—N1	−4.5 (6)
O1—S1—N1—C8	−62.4 (3)	O3—C7—C8—C9	−3.8 (6)
C1—S1—N1—C8	50.2 (3)	C6—C7—C8—C9	175.9 (3)
O2—S1—C1—C2	33.6 (4)	S1—N1—C8—C7	−34.2 (5)
O1—S1—C1—C2	−98.3 (4)	S1—N1—C8—C9	145.4 (3)
N1—S1—C1—C2	148.3 (3)	C7—C8—C9—O4	1.7 (6)
O2—S1—C1—C6	−151.4 (3)	N1—C8—C9—O4	−177.9 (3)
O1—S1—C1—C6	76.7 (3)	C7—C8—C9—C10	−178.0 (3)
N1—S1—C1—C6	−36.7 (3)	N1—C8—C9—C10	2.4 (5)
C6—C1—C2—C3	−1.5 (6)	O4—C9—C10—C15	117.4 (4)
S1—C1—C2—C3	173.3 (3)	C8—C9—C10—C15	−63.0 (5)
C1—C2—C3—C4	0.6 (7)	O4—C9—C10—C11	−58.7 (5)
C2—C3—C4—C5	−0.2 (7)	C8—C9—C10—C11	120.9 (4)
C3—C4—C5—C6	0.7 (6)	C15—C10—C11—C12	0.3 (6)
C4—C5—C6—C1	−1.6 (6)	C9—C10—C11—C12	176.4 (4)
C4—C5—C6—C7	178.7 (4)	C15—C10—C11—Cl1	176.4 (3)
C2—C1—C6—C5	2.0 (6)	C9—C10—C11—Cl1	−7.5 (5)
S1—C1—C6—C5	−173.0 (3)	C10—C11—C12—C13	−1.5 (6)
C2—C1—C6—C7	−178.4 (4)	Cl1—C11—C12—C13	−177.7 (3)
S1—C1—C6—C7	6.6 (5)	C11—C12—C13—C14	0.6 (7)
C5—C6—C7—O3	17.5 (5)	C12—C13—C14—C15	1.5 (7)
C1—C6—C7—O3	−162.2 (3)	C11—C10—C15—C14	1.8 (6)
C5—C6—C7—C8	−162.3 (4)	C9—C10—C15—C14	−174.4 (4)
C1—C6—C7—C8	18.0 (6)	C13—C14—C15—C10	−2.7 (6)
O3—C7—C8—N1	175.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4i	0.84 (4)	2.06 (4)	2.857 (4)	158 (4)
C13—H13···O2ii	0.95	2.59	3.307 (5)	132
C5—H5···O1iii	0.95	2.55	3.369 (5)	145
O3—H3O···O4	0.84	1.80	2.536 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4i	0.84 (4)	2.06 (4)	2.857 (4)	158 (4)
C13—H13⋯O2ii	0.95	2.59	3.307 (5)	132
C5—H5⋯O1iii	0.95	2.55	3.369 (5)	145
O3—H3O⋯O4	0.84	1.80	2.536 (3)	146

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