3-Benzoyl-4-hydr-oxy-2-methyl-2H-1,2-benzothia-zine 1,1-dioxide.

In the title mol-ecule, C(16)H(13)NO(4)S, the heterocyclic thia-zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.410 (3) and 0.299 (3) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The crystal structure is stabilized by inter-molecular hydrogen bonds of the types O-H⋯O and C-H⋯O; the former result in dimers lying about inversion centers and the latter form chains of mol-ecules running along the c axis. In addition, intra-molecular O-H⋯O links are present.

Related literature

For 1,2-benzothia­zine derivatives as anti-inflammatory drugs (NSAIDs), see: Lombardino et al. (1971 ▶); Soler (1985 ▶); Carty et al. (1993 ▶); Turck et al. (1995 ▶). For the synthesis of benzothia­zine derivatives, see: Siddiqui et al. (2007 ▶); Ahmad, Siddiqui, Zia-ur-Rehman et al. (2010 ▶). For related structures, see: Siddiqui et al. (2008 ▶); Ahmad, Siddiqui, Rizvi et al. (2010 ▶).

Experimental

Crystal data

C16H13NO4S

M = 315.33

Triclinic,

a = 6.8342 (3) Å

b = 9.9085 (3) Å

c = 10.7234 (4) Å

α = 83.257 (2)°

β = 79.481 (2)°

γ = 85.113 (2)°

V = 707.50 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 173 K

0.12 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.971, T max = 0.981

7177 measured reflections

4080 independent reflections

3665 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.09

4080 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.34 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/S1600536810011025/jh2140sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011025/jh2140Isup2.hkl

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

C16H13NO4S	Z = 2
Mr = 315.33	F(000) = 328
Triclinic, P1	Dx = 1.480 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8342 (3) Å	Cell parameters from 3532 reflections
b = 9.9085 (3) Å	θ = 1.0–30.0°
c = 10.7234 (4) Å	µ = 0.25 mm−1
α = 83.257 (2)°	T = 173 K
β = 79.481 (2)°	Block, pale-yellow
γ = 85.113 (2)°	0.12 × 0.10 × 0.08 mm
V = 707.50 (5) Å3

Nonius KappaCCD diffractometer	4080 independent reflections
Radiation source: fine-focus sealed tube	3665 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω and φ scans	θmax = 30.1°, θmin = 2.1°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −9→9
Tmin = 0.971, Tmax = 0.981	k = −13→13
7177 measured reflections	l = −15→15

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0468P)2 + 0.3608P] where P = (Fo2 + 2Fc2)/3
4080 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.34 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 > 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	0.20282 (5)	0.24470 (3)	0.28051 (3)	0.02305 (10)
O1	−0.00548 (16)	0.28521 (10)	0.28975 (11)	0.0279 (2)
O2	0.29460 (19)	0.15793 (11)	0.18540 (11)	0.0339 (3)
O3	0.23671 (18)	0.47875 (11)	0.58638 (10)	0.0290 (2)
H3O	0.2333	0.5621	0.5604	0.044*
O4	0.24683 (18)	0.68733 (10)	0.42430 (10)	0.0303 (2)
N1	0.32262 (17)	0.38365 (11)	0.25903 (11)	0.0218 (2)
C1	0.2435 (2)	0.17087 (13)	0.43178 (14)	0.0230 (3)
C2	0.2400 (2)	0.03080 (14)	0.46264 (16)	0.0284 (3)
H2	0.2244	−0.0268	0.4008	0.034*
C3	0.2596 (2)	−0.02341 (15)	0.58521 (17)	0.0321 (3)
H3	0.2570	−0.1189	0.6078	0.039*
C4	0.2832 (2)	0.06112 (16)	0.67508 (16)	0.0325 (3)
H4	0.2965	0.0229	0.7588	0.039*
C5	0.2875 (2)	0.20118 (15)	0.64393 (14)	0.0279 (3)
H5	0.3035	0.2582	0.7062	0.033*
C6	0.2683 (2)	0.25797 (13)	0.52084 (13)	0.0228 (3)
C7	0.2650 (2)	0.40639 (13)	0.48734 (13)	0.0218 (2)
C8	0.2777 (2)	0.46608 (13)	0.36361 (13)	0.0205 (2)
C9	0.2466 (2)	0.61275 (13)	0.33796 (13)	0.0222 (2)
C10	0.5305 (2)	0.38032 (17)	0.19048 (16)	0.0336 (3)
H10A	0.5688	0.4736	0.1624	0.040*
H10B	0.5419	0.3296	0.1161	0.040*
H10C	0.6189	0.3356	0.2474	0.040*
C11	0.2056 (2)	0.67762 (13)	0.21160 (13)	0.0227 (3)
C12	0.0803 (2)	0.61998 (14)	0.14609 (14)	0.0254 (3)
H12	0.0330	0.5325	0.1758	0.030*
C13	0.0252 (2)	0.69159 (15)	0.03694 (14)	0.0283 (3)
H13	−0.0619	0.6535	−0.0071	0.034*
C14	0.0968 (3)	0.81858 (15)	−0.00811 (15)	0.0304 (3)
H14	0.0587	0.8668	−0.0828	0.036*
C15	0.2239 (3)	0.87500 (15)	0.05592 (15)	0.0309 (3)
H15	0.2752	0.9609	0.0240	0.037*
C16	0.2759 (2)	0.80577 (14)	0.16662 (14)	0.0270 (3)
H16	0.3595	0.8456	0.2119	0.032*

	U11	U22	U33	U12	U13	U23
S1	0.02533 (17)	0.02010 (16)	0.02556 (17)	−0.00128 (11)	−0.00723 (12)	−0.00570 (11)
O1	0.0246 (5)	0.0277 (5)	0.0338 (6)	−0.0033 (4)	−0.0113 (4)	−0.0022 (4)
O2	0.0448 (7)	0.0258 (5)	0.0331 (6)	0.0001 (4)	−0.0074 (5)	−0.0127 (4)
O3	0.0404 (6)	0.0251 (5)	0.0231 (5)	0.0006 (4)	−0.0084 (4)	−0.0063 (4)
O4	0.0444 (6)	0.0224 (5)	0.0263 (5)	−0.0038 (4)	−0.0088 (4)	−0.0065 (4)
N1	0.0218 (5)	0.0210 (5)	0.0224 (5)	−0.0014 (4)	−0.0020 (4)	−0.0053 (4)
C1	0.0189 (6)	0.0221 (6)	0.0281 (7)	−0.0007 (4)	−0.0050 (5)	−0.0017 (5)
C2	0.0218 (6)	0.0220 (6)	0.0412 (8)	−0.0019 (5)	−0.0061 (6)	−0.0017 (5)
C3	0.0234 (7)	0.0245 (6)	0.0460 (9)	−0.0031 (5)	−0.0055 (6)	0.0068 (6)
C4	0.0278 (7)	0.0326 (7)	0.0337 (8)	−0.0019 (6)	−0.0045 (6)	0.0093 (6)
C5	0.0261 (7)	0.0311 (7)	0.0256 (7)	−0.0004 (5)	−0.0053 (5)	0.0012 (5)
C6	0.0194 (6)	0.0230 (6)	0.0254 (6)	−0.0004 (4)	−0.0040 (5)	−0.0010 (5)
C7	0.0212 (6)	0.0226 (6)	0.0226 (6)	−0.0010 (4)	−0.0054 (5)	−0.0038 (5)
C8	0.0209 (6)	0.0202 (5)	0.0211 (6)	−0.0011 (4)	−0.0041 (4)	−0.0042 (4)
C9	0.0227 (6)	0.0211 (6)	0.0234 (6)	−0.0033 (4)	−0.0039 (5)	−0.0032 (4)
C10	0.0259 (7)	0.0364 (8)	0.0373 (8)	−0.0034 (6)	0.0036 (6)	−0.0123 (6)
C11	0.0255 (6)	0.0200 (6)	0.0222 (6)	0.0002 (5)	−0.0033 (5)	−0.0033 (4)
C12	0.0278 (7)	0.0232 (6)	0.0258 (6)	−0.0021 (5)	−0.0054 (5)	−0.0036 (5)
C13	0.0319 (7)	0.0287 (7)	0.0261 (7)	−0.0005 (5)	−0.0093 (6)	−0.0046 (5)
C14	0.0391 (8)	0.0266 (7)	0.0249 (7)	0.0036 (6)	−0.0077 (6)	−0.0012 (5)
C15	0.0404 (8)	0.0216 (6)	0.0301 (7)	−0.0031 (5)	−0.0058 (6)	0.0005 (5)
C16	0.0312 (7)	0.0217 (6)	0.0294 (7)	−0.0034 (5)	−0.0070 (6)	−0.0036 (5)

S1—O2	1.4329 (11)	C6—C7	1.4716 (18)
S1—O1	1.4346 (11)	C7—C8	1.3784 (19)
S1—N1	1.6333 (12)	C8—C9	1.4518 (18)
S1—C1	1.7593 (14)	C9—C11	1.4936 (19)
O3—C7	1.3265 (16)	C10—H10A	0.9800
O3—H3O	0.8400	C10—H10B	0.9800
O4—C9	1.2509 (16)	C10—H10C	0.9800
N1—C8	1.4373 (16)	C11—C12	1.3966 (19)
N1—C10	1.4753 (18)	C11—C16	1.3969 (19)
C1—C2	1.3896 (19)	C12—C13	1.391 (2)
C1—C6	1.4011 (19)	C12—H12	0.9500
C2—C3	1.386 (2)	C13—C14	1.390 (2)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.388 (2)	C14—C15	1.389 (2)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.390 (2)	C15—C16	1.388 (2)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.3974 (19)	C16—H16	0.9500
C5—H5	0.9500
O2—S1—O1	118.95 (7)	C7—C8—N1	120.26 (11)
O2—S1—N1	108.49 (7)	C7—C8—C9	120.23 (12)
O1—S1—N1	107.25 (6)	N1—C8—C9	119.51 (12)
O2—S1—C1	109.77 (7)	O4—C9—C8	119.85 (12)
O1—S1—C1	107.98 (6)	O4—C9—C11	118.55 (12)
N1—S1—C1	103.26 (6)	C8—C9—C11	121.55 (12)
C7—O3—H3O	109.5	N1—C10—H10A	109.5
C8—N1—C10	116.02 (11)	N1—C10—H10B	109.5
C8—N1—S1	114.56 (9)	H10A—C10—H10B	109.5
C10—N1—S1	118.88 (9)	N1—C10—H10C	109.5
C2—C1—C6	121.72 (13)	H10A—C10—H10C	109.5
C2—C1—S1	120.23 (11)	H10B—C10—H10C	109.5
C6—C1—S1	117.96 (10)	C12—C11—C16	119.90 (13)
C3—C2—C1	118.87 (14)	C12—C11—C9	121.08 (12)
C3—C2—H2	120.6	C16—C11—C9	118.60 (12)
C1—C2—H2	120.6	C13—C12—C11	119.51 (13)
C2—C3—C4	120.34 (14)	C13—C12—H12	120.2
C2—C3—H3	119.8	C11—C12—H12	120.2
C4—C3—H3	119.8	C14—C13—C12	120.42 (14)
C3—C4—C5	120.73 (15)	C14—C13—H13	119.8
C3—C4—H4	119.6	C12—C13—H13	119.8
C5—C4—H4	119.6	C15—C14—C13	120.07 (14)
C4—C5—C6	119.87 (15)	C15—C14—H14	120.0
C4—C5—H5	120.1	C13—C14—H14	120.0
C6—C5—H5	120.1	C16—C15—C14	119.93 (14)
C5—C6—C1	118.46 (13)	C16—C15—H15	120.0
C5—C6—C7	120.69 (13)	C14—C15—H15	120.0
C1—C6—C7	120.79 (12)	C15—C16—C11	120.14 (14)
O3—C7—C8	122.43 (12)	C15—C16—H16	119.9
O3—C7—C6	114.62 (12)	C11—C16—H16	119.9
C8—C7—C6	122.84 (12)
O2—S1—N1—C8	−166.36 (9)	C1—C6—C7—C8	−13.2 (2)
O1—S1—N1—C8	63.98 (11)	O3—C7—C8—N1	175.55 (12)
C1—S1—N1—C8	−49.92 (11)	C6—C7—C8—N1	−8.6 (2)
O2—S1—N1—C10	−22.94 (13)	O3—C7—C8—C9	−4.2 (2)
O1—S1—N1—C10	−152.60 (11)	C6—C7—C8—C9	171.61 (12)
C1—S1—N1—C10	93.50 (12)	C10—N1—C8—C7	−100.95 (16)
O2—S1—C1—C2	−37.60 (14)	S1—N1—C8—C7	43.55 (16)
O1—S1—C1—C2	93.50 (12)	C10—N1—C8—C9	78.84 (16)
N1—S1—C1—C2	−153.13 (11)	S1—N1—C8—C9	−136.66 (11)
O2—S1—C1—C6	145.77 (11)	C7—C8—C9—O4	13.9 (2)
O1—S1—C1—C6	−83.13 (12)	N1—C8—C9—O4	−165.87 (13)
N1—S1—C1—C6	30.25 (12)	C7—C8—C9—C11	−163.55 (13)
C6—C1—C2—C3	0.6 (2)	N1—C8—C9—C11	16.66 (19)
S1—C1—C2—C3	−175.86 (11)	O4—C9—C11—C12	−137.23 (14)
C1—C2—C3—C4	−0.3 (2)	C8—C9—C11—C12	40.27 (19)
C2—C3—C4—C5	0.0 (2)	O4—C9—C11—C16	35.29 (19)
C3—C4—C5—C6	−0.1 (2)	C8—C9—C11—C16	−147.21 (14)
C4—C5—C6—C1	0.4 (2)	C16—C11—C12—C13	−0.6 (2)
C4—C5—C6—C7	177.71 (13)	C9—C11—C12—C13	171.87 (13)
C2—C1—C6—C5	−0.7 (2)	C11—C12—C13—C14	1.1 (2)
S1—C1—C6—C5	175.85 (10)	C12—C13—C14—C15	−0.1 (2)
C2—C1—C6—C7	−178.00 (13)	C13—C14—C15—C16	−1.4 (2)
S1—C1—C6—C7	−1.42 (18)	C14—C15—C16—C11	2.0 (2)
C5—C6—C7—O3	−14.30 (19)	C12—C11—C16—C15	−1.0 (2)
C1—C6—C7—O3	162.91 (13)	C9—C11—C16—C15	−173.59 (13)
C5—C6—C7—C8	169.55 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4	0.84	1.80	2.5365 (15)	146
O3—H3O···O1i	0.84	2.56	3.0108 (15)	115
C3—H3···O1ii	0.95	2.50	3.2627 (18)	138
C12—H12···N1	0.95	2.59	3.0163 (18)	107

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4	0.84	1.80	2.5365 (15)	146
O3—H3O⋯O1i	0.84	2.56	3.0108 (15)	115
C3—H3⋯O1ii	0.95	2.50	3.2627 (18)	138

Symmetry codes: (i) ; (ii) .