3-(3-Chloro-benzo-yl)-4-hydr-oxy-2H-1,2-benzothia-zine 1,1-dioxide.

In the title compound, 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 0.476 (5) and 0.227 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The structure is stabilized by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds. In addition, intra-molecular O-H⋯O and C-H⋯N inter-actions are also present.

Related literature

For the biological activity of 1,2-benzothia­zine derivatives, see: Ahmad et al. (2010 ▶); Lombardino & Wiseman, (1972 ▶); Gupta et al. (1993 ▶, 2002 ▶); Zia-ur-Rehman et al. (2006 ▶); Berryman et al. (1998 ▶). For comparative bond distances, see: Allen et al. (1987 ▶). For related structures, see: Siddiqui et al. (2008 ▶)

Experimental

Crystal data

C15H10ClNO4S

M = 335.75

Triclinic,

a = 4.7151 (3) Å

b = 12.2879 (8) Å

c = 12.5809 (6) Å

α = 81.375 (3)°

β = 84.463 (3)°

γ = 85.608 (3)°

V = 715.88 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.43 mm−1

T = 295 K

0.14 × 0.12 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.942, T max = 0.958

4352 measured reflections

3202 independent reflections

2783 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.121

S = 1.09

3202 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.45 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 datablocks global, I. DOI: 10.1107/S1600536810009761/pk2231sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009761/pk2231Isup2.hkl

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

C15H10ClNO4S	Z = 2
Mr = 335.75	F(000) = 344
Triclinic, P1	Dx = 1.558 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.7151 (3) Å	Cell parameters from 1649 reflections
b = 12.2879 (8) Å	θ = 1.0–27.5°
c = 12.5809 (6) Å	µ = 0.43 mm−1
α = 81.375 (3)°	T = 295 K
β = 84.463 (3)°	Block, yellow
γ = 85.608 (3)°	0.14 × 0.12 × 0.10 mm
V = 715.88 (7) Å3

Nonius KappaCCD diffractometer	3202 independent reflections
Radiation source: fine-focus sealed tube	2783 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω and φ scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −6→6
Tmin = 0.942, Tmax = 0.958	k = −15→15
4352 measured reflections	l = −16→16

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)] = 0.051	Hydrogen site location: difference Fourier map
wR(F2) = 0.121	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.025P)2 + 0.745P] where P = (Fo2 + 2Fc2)/3
3202 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Experimental. IR (KBr) 3157, 1615, 1358, 1156 cm-1, MS m/z: 335.2 [M+]. 1H NMR (DMSO-d6); 7.64 (t, 2H, J = 8.0 Hz, Ar—H), 7.75 (d, 2H, J = 8.0 Hz, Ar—H), 7.96 (d, 1H, J = 10.0 Hz, Ar—H), 7.96 (s, 1H, J = 16.4 Hz, Ar—H), 8.18 (t, 2H, J = 3.2 Hz, Ar—H).

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 > 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	1.12832 (17)	−0.15369 (6)	0.14547 (7)	0.0618 (2)
S1	−0.00971 (13)	0.31098 (5)	0.38523 (5)	0.03988 (17)
O1	0.1096 (5)	0.34309 (18)	0.47468 (16)	0.0601 (6)
O2	−0.2260 (4)	0.23281 (16)	0.40650 (15)	0.0511 (5)
O3	−0.0663 (5)	0.30935 (17)	0.04835 (15)	0.0604 (6)
H3O	0.0372	0.2596	0.0257	0.073*
O4	0.3079 (4)	0.15059 (17)	0.05644 (14)	0.0553 (5)
N1	0.2456 (4)	0.26558 (18)	0.30655 (17)	0.0441 (5)
H1N	0.4144	0.2519	0.3277	0.053*
C1	−0.1507 (5)	0.4240 (2)	0.3008 (2)	0.0415 (5)
C2	−0.2846 (7)	0.5148 (2)	0.3434 (3)	0.0563 (7)
H2	−0.2815	0.5204	0.4162	0.068*
C3	−0.4223 (8)	0.5961 (3)	0.2754 (3)	0.0715 (10)
H3	−0.5125	0.6575	0.3025	0.086*
C4	−0.4271 (9)	0.5873 (3)	0.1678 (3)	0.0748 (10)
H4	−0.5241	0.6421	0.1233	0.090*
C5	−0.2904 (7)	0.4985 (3)	0.1253 (3)	0.0623 (8)
H5	−0.2926	0.4943	0.0522	0.075*
C6	−0.1488 (5)	0.4148 (2)	0.1915 (2)	0.0425 (5)
C7	−0.0006 (5)	0.3206 (2)	0.1462 (2)	0.0415 (5)
C8	0.1900 (5)	0.2482 (2)	0.20148 (19)	0.0386 (5)
C9	0.3263 (5)	0.1547 (2)	0.1542 (2)	0.0407 (5)
C10	0.4876 (5)	0.0619 (2)	0.21729 (19)	0.0394 (5)
C11	0.7101 (5)	0.0062 (2)	0.1617 (2)	0.0413 (5)
H11	0.7634	0.0309	0.0895	0.050*
C12	0.8495 (5)	−0.0854 (2)	0.2149 (2)	0.0435 (6)
C13	0.7712 (7)	−0.1251 (2)	0.3214 (2)	0.0553 (7)
H13	0.8680	−0.1870	0.3562	0.066*
C14	0.5477 (7)	−0.0714 (2)	0.3752 (2)	0.0589 (8)
H14	0.4910	−0.0984	0.4465	0.071*
C15	0.4057 (6)	0.0222 (2)	0.3248 (2)	0.0494 (6)
H15	0.2568	0.0583	0.3623	0.059*

	U11	U22	U33	U12	U13	U23
Cl1	0.0599 (4)	0.0588 (4)	0.0699 (5)	0.0225 (3)	−0.0186 (4)	−0.0246 (4)
S1	0.0367 (3)	0.0471 (3)	0.0379 (3)	0.0050 (2)	−0.0090 (2)	−0.0131 (2)
O1	0.0647 (13)	0.0721 (14)	0.0503 (11)	0.0158 (10)	−0.0234 (10)	−0.0297 (10)
O2	0.0417 (10)	0.0556 (11)	0.0526 (11)	−0.0028 (8)	−0.0053 (8)	0.0035 (9)
O3	0.0839 (15)	0.0576 (13)	0.0399 (10)	0.0222 (11)	−0.0180 (10)	−0.0126 (9)
O4	0.0659 (13)	0.0607 (12)	0.0395 (10)	0.0191 (10)	−0.0104 (9)	−0.0160 (8)
N1	0.0318 (10)	0.0567 (13)	0.0484 (12)	0.0085 (9)	−0.0125 (9)	−0.0226 (10)
C1	0.0394 (13)	0.0387 (12)	0.0480 (14)	0.0002 (10)	−0.0061 (10)	−0.0116 (10)
C2	0.0612 (18)	0.0490 (16)	0.0619 (17)	0.0089 (13)	−0.0079 (14)	−0.0232 (13)
C3	0.084 (2)	0.0411 (16)	0.089 (3)	0.0195 (15)	−0.0117 (19)	−0.0194 (15)
C4	0.095 (3)	0.0494 (18)	0.075 (2)	0.0278 (17)	−0.0176 (19)	−0.0025 (15)
C5	0.078 (2)	0.0501 (17)	0.0551 (17)	0.0170 (15)	−0.0116 (15)	−0.0028 (13)
C6	0.0442 (13)	0.0365 (12)	0.0466 (14)	0.0033 (10)	−0.0058 (11)	−0.0067 (10)
C7	0.0455 (13)	0.0409 (13)	0.0389 (12)	0.0028 (10)	−0.0068 (10)	−0.0092 (10)
C8	0.0358 (12)	0.0424 (13)	0.0390 (12)	0.0015 (10)	−0.0045 (9)	−0.0118 (10)
C9	0.0389 (12)	0.0435 (13)	0.0409 (13)	0.0001 (10)	−0.0036 (10)	−0.0109 (10)
C10	0.0428 (13)	0.0381 (12)	0.0385 (12)	−0.0001 (10)	−0.0051 (10)	−0.0094 (9)
C11	0.0445 (13)	0.0420 (13)	0.0387 (12)	0.0008 (10)	−0.0066 (10)	−0.0099 (10)
C12	0.0437 (13)	0.0426 (13)	0.0476 (14)	0.0028 (10)	−0.0130 (11)	−0.0140 (11)
C13	0.073 (2)	0.0411 (14)	0.0527 (16)	0.0030 (13)	−0.0202 (14)	−0.0049 (12)
C14	0.082 (2)	0.0514 (16)	0.0420 (15)	−0.0081 (15)	−0.0055 (14)	−0.0009 (12)
C15	0.0567 (16)	0.0492 (15)	0.0428 (14)	−0.0057 (12)	0.0035 (12)	−0.0122 (11)

Cl1—C12	1.739 (3)	C4—H4	0.9300
S1—O1	1.4240 (18)	C5—C6	1.394 (4)
S1—O2	1.434 (2)	C5—H5	0.9300
S1—N1	1.604 (2)	C6—C7	1.467 (3)
S1—C1	1.747 (3)	C7—C8	1.377 (3)
O3—C7	1.327 (3)	C8—C9	1.451 (3)
O3—H3O	0.8200	C9—C10	1.491 (3)
O4—C9	1.250 (3)	C10—C15	1.395 (4)
N1—C8	1.422 (3)	C10—C11	1.396 (3)
N1—H1N	0.8600	C11—C12	1.376 (3)
C1—C2	1.391 (4)	C11—H11	0.9300
C1—C6	1.396 (3)	C12—C13	1.380 (4)
C2—C3	1.380 (4)	C13—C14	1.376 (4)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.377 (5)	C14—C15	1.385 (4)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.376 (4)	C15—H15	0.9300
O1—S1—O2	118.25 (13)	O3—C7—C8	122.4 (2)
O1—S1—N1	108.39 (12)	O3—C7—C6	115.1 (2)
O2—S1—N1	109.12 (12)	C8—C7—C6	122.6 (2)
O1—S1—C1	112.18 (12)	C7—C8—N1	118.7 (2)
O2—S1—C1	106.33 (11)	C7—C8—C9	120.5 (2)
N1—S1—C1	101.20 (12)	N1—C8—C9	120.8 (2)
C7—O3—H3O	109.5	O4—C9—C8	119.2 (2)
C8—N1—S1	119.34 (16)	O4—C9—C10	117.9 (2)
C8—N1—H1N	120.3	C8—C9—C10	122.9 (2)
S1—N1—H1N	120.3	C15—C10—C11	119.6 (2)
C2—C1—C6	121.6 (2)	C15—C10—C9	122.6 (2)
C2—C1—S1	120.7 (2)	C11—C10—C9	117.4 (2)
C6—C1—S1	117.43 (18)	C12—C11—C10	119.3 (2)
C3—C2—C1	118.6 (3)	C12—C11—H11	120.4
C3—C2—H2	120.7	C10—C11—H11	120.4
C1—C2—H2	120.7	C11—C12—C13	121.6 (2)
C4—C3—C2	120.6 (3)	C11—C12—Cl1	119.0 (2)
C4—C3—H3	119.7	C13—C12—Cl1	119.3 (2)
C2—C3—H3	119.7	C14—C13—C12	118.9 (3)
C5—C4—C3	120.9 (3)	C14—C13—H13	120.5
C5—C4—H4	119.6	C12—C13—H13	120.5
C3—C4—H4	119.6	C13—C14—C15	121.0 (3)
C4—C5—C6	120.2 (3)	C13—C14—H14	119.5
C4—C5—H5	119.9	C15—C14—H14	119.5
C6—C5—H5	119.9	C14—C15—C10	119.6 (3)
C5—C6—C1	118.2 (2)	C14—C15—H15	120.2
C5—C6—C7	120.3 (2)	C10—C15—H15	120.2
C1—C6—C7	121.5 (2)
O1—S1—N1—C8	−167.9 (2)	O3—C7—C8—N1	−179.3 (2)
O2—S1—N1—C8	62.0 (2)	C6—C7—C8—N1	−0.1 (4)
C1—S1—N1—C8	−49.8 (2)	O3—C7—C8—C9	−0.6 (4)
O1—S1—C1—C2	−35.9 (3)	C6—C7—C8—C9	178.6 (2)
O2—S1—C1—C2	94.9 (2)	S1—N1—C8—C7	36.5 (3)
N1—S1—C1—C2	−151.2 (2)	S1—N1—C8—C9	−142.2 (2)
O1—S1—C1—C6	150.4 (2)	C7—C8—C9—O4	12.1 (4)
O2—S1—C1—C6	−78.9 (2)	N1—C8—C9—O4	−169.2 (2)
N1—S1—C1—C6	35.0 (2)	C7—C8—C9—C10	−167.5 (2)
C6—C1—C2—C3	1.1 (5)	N1—C8—C9—C10	11.2 (4)
S1—C1—C2—C3	−172.4 (3)	O4—C9—C10—C15	−143.7 (3)
C1—C2—C3—C4	0.2 (5)	C8—C9—C10—C15	35.9 (4)
C2—C3—C4—C5	−1.3 (6)	O4—C9—C10—C11	29.3 (3)
C3—C4—C5—C6	1.2 (6)	C8—C9—C10—C11	−151.1 (2)
C4—C5—C6—C1	0.1 (5)	C15—C10—C11—C12	−1.6 (4)
C4—C5—C6—C7	−179.4 (3)	C9—C10—C11—C12	−174.8 (2)
C2—C1—C6—C5	−1.2 (4)	C10—C11—C12—C13	1.3 (4)
S1—C1—C6—C5	172.5 (2)	C10—C11—C12—Cl1	−179.47 (18)
C2—C1—C6—C7	178.3 (3)	C11—C12—C13—C14	0.2 (4)
S1—C1—C6—C7	−8.0 (3)	Cl1—C12—C13—C14	−179.1 (2)
C5—C6—C7—O3	−14.6 (4)	C12—C13—C14—C15	−1.3 (5)
C1—C6—C7—O3	165.9 (2)	C13—C14—C15—C10	0.9 (4)
C5—C6—C7—C8	166.2 (3)	C11—C10—C15—C14	0.5 (4)
C1—C6—C7—C8	−13.3 (4)	C9—C10—C15—C14	173.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86	2.03	2.872 (3)	168
O3—H3O···O4	0.82	1.80	2.525 (3)	146
C2—H2···O1ii	0.93	2.54	3.279 (3)	136
C14—H14···O2iii	0.93	2.58	3.435 (3)	153
C15—H15···N1	0.93	2.54	3.009 (4)	112

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86	2.03	2.872 (3)	168
O3—H3O⋯O4	0.82	1.80	2.525 (3)	146
C2—H2⋯O1ii	0.93	2.54	3.279 (3)	136
C14—H14⋯O2iii	0.93	2.58	3.435 (3)	153
C15—H15⋯N1	0.93	2.54	3.009 (4)	112

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