1-(4-Hydr-oxy-2-methyl-1,1-dioxo-2H-1,2-benzothia-zin-3-yl)ethanone.

In the title compound, C(11)H(11)NO(4)S, the thia-zine ring adopts a distorted half-chair conformation. The enolic H atom is involved in an intra-molecular O-H⋯O hydrogen bond, forming a six-membered ring. Mol-ecules are linked through weak inter-molecular C-H⋯O hydrogen bonds, resulting in chains lying along the b axis.

Related literature

For related literature, see: Bihovsky et al. (2004 ▶); Fabiola et al. (1998 ▶); Golič & Leban (1987 ▶); Zia-ur-Rehman et al. (2005 ▶, 2006 ▶, 2007 ▶); Turck et al. (1996 ▶).

Experimental

Crystal data

C11H11NO4S

M = 253.27

Triclinic,

a = 6.8523 (1) Å

b = 8.3222 (2) Å

c = 10.4880 (2) Å

α = 72.1321 (11)°

β = 77.9619 (12)°

γ = 80.0360 (12)°

V = 552.89 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 120 (2) K

0.40 × 0.20 × 0.14 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.891, T max = 0.960

12691 measured reflections

2529 independent reflections

2248 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.11

2529 reflections

157 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.53 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CAMERON (Pearce & Watkin, 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808007721/pv2072sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007721/pv2072Isup2.hkl

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

C11H11NO4S	Z = 2
Mr = 253.27	F000 = 264
Triclinic, P1	Dx = 1.521 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.8523 (1) Å	Cell parameters from 15360 reflections
b = 8.3222 (2) Å	θ = 2.9–27.5º
c = 10.4880 (2) Å	µ = 0.30 mm−1
α = 72.1321 (11)º	T = 120 (2) K
β = 77.9619 (12)º	Shard, colourless
γ = 80.0360 (12)º	0.40 × 0.20 × 0.14 mm
V = 552.892 (19) Å3

Bruker–Nonius CCD camera on κ-goniostat diffractometer	2529 independent reflections
Radiation source: Bruker Nonius FR591 Rotating Anode	2248 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
Detector resolution: 9.091 pixels mm-1	θmax = 27.5º
T = 120(2) K	θmin = 3.1º
φ & ω scans to fill the asymmetric unit	h = −8→8
Absorption correction: multi-scan(SADABS; Sheldrick, 2007)	k = −10→10
Tmin = 0.891, Tmax = 0.960	l = −13→13
12691 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.041P)2 + 0.3066P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.030
2529 reflections	Δρmax = 0.31 e Å−3
157 parameters	Δρmin = −0.53 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.6696 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command

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
C1	0.3007 (2)	0.32223 (18)	0.37041 (14)	0.0135 (3)
C2	0.2992 (2)	0.31686 (19)	0.50412 (15)	0.0164 (3)
H2	0.3246	0.2117	0.5702	0.020*
C3	0.2595 (2)	0.4692 (2)	0.53933 (16)	0.0191 (3)
H3	0.2575	0.4684	0.6304	0.023*
C4	0.2228 (2)	0.6220 (2)	0.44168 (16)	0.0199 (3)
H4	0.1973	0.7252	0.4665	0.024*
C5	0.2229 (2)	0.62640 (19)	0.30802 (15)	0.0184 (3)
H5	0.1983	0.7320	0.2422	0.022*
C6	0.2593 (2)	0.47505 (18)	0.27093 (14)	0.0148 (3)
C7	0.2558 (2)	0.47385 (19)	0.13150 (14)	0.0153 (3)
C8	0.2396 (2)	0.32881 (19)	0.09905 (14)	0.0157 (3)
C9	0.2507 (2)	0.3316 (2)	−0.04098 (16)	0.0204 (3)
C10	0.2518 (3)	0.1701 (2)	−0.07671 (18)	0.0332 (4)
H10A	0.1136	0.1532	−0.0764	0.050*
H10B	0.3113	0.0740	−0.0098	0.050*
H10C	0.3310	0.1775	−0.1672	0.050*
C11	0.0024 (2)	0.1379 (2)	0.25625 (16)	0.0210 (3)
H11A	−0.0710	0.2301	0.2933	0.031*
H11B	−0.0022	0.0298	0.3279	0.031*
H11C	−0.0598	0.1321	0.1819	0.031*
N1	0.21494 (18)	0.17080 (16)	0.20411 (12)	0.0152 (3)
O1	0.56456 (16)	0.12980 (14)	0.24794 (11)	0.0202 (2)
O2	0.30103 (17)	−0.00587 (13)	0.42939 (11)	0.0212 (3)
O3	0.27313 (18)	0.62312 (14)	0.03808 (11)	0.0220 (3)
H3A	0.2785	0.6110	−0.0392	0.033*
O4	0.26152 (18)	0.46897 (16)	−0.13289 (11)	0.0264 (3)
S1	0.36145 (5)	0.13574 (4)	0.31790 (3)	0.01424 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0111 (6)	0.0140 (7)	0.0157 (7)	−0.0025 (5)	−0.0013 (5)	−0.0046 (5)
C2	0.0141 (7)	0.0192 (7)	0.0154 (7)	−0.0029 (6)	−0.0034 (5)	−0.0033 (6)
C3	0.0167 (7)	0.0257 (8)	0.0181 (7)	−0.0037 (6)	−0.0031 (6)	−0.0101 (6)
C4	0.0189 (7)	0.0187 (8)	0.0251 (8)	−0.0044 (6)	−0.0014 (6)	−0.0107 (6)
C5	0.0181 (7)	0.0145 (7)	0.0205 (7)	−0.0024 (5)	−0.0011 (6)	−0.0032 (6)
C6	0.0128 (7)	0.0160 (7)	0.0148 (7)	−0.0026 (5)	−0.0010 (5)	−0.0034 (5)
C7	0.0120 (7)	0.0171 (7)	0.0132 (7)	0.0003 (5)	−0.0008 (5)	−0.0009 (5)
C8	0.0135 (7)	0.0193 (7)	0.0129 (7)	0.0005 (5)	−0.0023 (5)	−0.0037 (5)
C9	0.0164 (7)	0.0277 (8)	0.0176 (7)	0.0039 (6)	−0.0049 (6)	−0.0092 (6)
C10	0.0463 (11)	0.0342 (10)	0.0245 (9)	0.0043 (8)	−0.0133 (8)	−0.0164 (7)
C11	0.0152 (7)	0.0230 (8)	0.0249 (8)	−0.0049 (6)	−0.0035 (6)	−0.0056 (6)
N1	0.0144 (6)	0.0165 (6)	0.0157 (6)	−0.0018 (5)	−0.0045 (5)	−0.0050 (5)
O1	0.0138 (5)	0.0234 (6)	0.0246 (6)	0.0025 (4)	−0.0036 (4)	−0.0108 (5)
O2	0.0292 (6)	0.0133 (5)	0.0202 (5)	−0.0044 (4)	−0.0086 (5)	0.0005 (4)
O3	0.0287 (6)	0.0182 (6)	0.0143 (5)	−0.0019 (5)	−0.0022 (5)	0.0009 (4)
O4	0.0300 (6)	0.0322 (7)	0.0140 (5)	0.0020 (5)	−0.0058 (5)	−0.0038 (5)
S1	0.01453 (19)	0.01270 (19)	0.01608 (19)	0.00015 (13)	−0.00467 (13)	−0.00442 (13)

C1—C2	1.387 (2)	C8—C9	1.448 (2)
C1—C6	1.404 (2)	C9—O4	1.251 (2)
C1—S1	1.7580 (14)	C9—C10	1.501 (2)
C2—C3	1.394 (2)	C10—H10A	0.9800
C2—H2	0.9500	C10—H10B	0.9800
C3—C4	1.388 (2)	C10—H10C	0.9800
C3—H3	0.9500	C11—N1	1.4864 (19)
C4—C5	1.391 (2)	C11—H11A	0.9800
C4—H4	0.9500	C11—H11B	0.9800
C5—C6	1.397 (2)	C11—H11C	0.9800
C5—H5	0.9500	N1—S1	1.6438 (12)
C6—C7	1.471 (2)	O1—S1	1.4319 (11)
C7—O3	1.3316 (17)	O2—S1	1.4314 (11)
C7—C8	1.378 (2)	O3—H3A	0.8400
C8—N1	1.4430 (18)
C2—C1—C6	122.15 (13)	O4—C9—C10	119.76 (14)
C2—C1—S1	120.70 (11)	C8—C9—C10	120.31 (15)
C6—C1—S1	117.13 (11)	C9—C10—H10A	109.5
C1—C2—C3	118.54 (14)	C9—C10—H10B	109.5
C1—C2—H2	120.7	H10A—C10—H10B	109.5
C3—C2—H2	120.7	C9—C10—H10C	109.5
C4—C3—C2	120.14 (14)	H10A—C10—H10C	109.5
C4—C3—H3	119.9	H10B—C10—H10C	109.5
C2—C3—H3	119.9	N1—C11—H11A	109.5
C3—C4—C5	121.04 (14)	N1—C11—H11B	109.5
C3—C4—H4	119.5	H11A—C11—H11B	109.5
C5—C4—H4	119.5	N1—C11—H11C	109.5
C4—C5—C6	119.79 (14)	H11A—C11—H11C	109.5
C4—C5—H5	120.1	H11B—C11—H11C	109.5
C6—C5—H5	120.1	C8—N1—C11	114.26 (11)
C5—C6—C1	118.30 (13)	C8—N1—S1	112.75 (10)
C5—C6—C7	121.47 (13)	C11—N1—S1	116.79 (10)
C1—C6—C7	120.23 (13)	C7—O3—H3A	109.5
O3—C7—C8	122.30 (13)	O2—S1—O1	119.39 (7)
O3—C7—C6	114.96 (13)	O2—S1—N1	108.47 (7)
C8—C7—C6	122.73 (13)	O1—S1—N1	107.24 (6)
C7—C8—N1	120.44 (12)	O2—S1—C1	109.27 (7)
C7—C8—C9	120.64 (14)	O1—S1—C1	108.93 (7)
N1—C8—C9	118.91 (13)	N1—S1—C1	102.15 (6)
O4—C9—C8	119.92 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4	0.84	1.78	2.525 (2)	146
C4—H4···O2i	0.95	2.36	3.193 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O4	0.84	1.78	2.525 (2)	146
C4—H4⋯O2i	0.95	2.36	3.193 (2)	146

Symmetry code: (i) .