Methyl 2-acetonyl-4-hydr-oxy-2H-1,2-benzothia-zine-3-carboxyl-ate 1,1-dioxide.

In the mol-ecule of the title compound, C(13)H(13)NO(6)S, the thia-zine ring adopts a distorted sofa conformation. The enolic H atom is involved in intra-molecular O-H⋯O hydrogen bonding besides the weaker C-H⋯O=S and C-H⋯O=C inter-actions.

Related literature

For related literature, see: Ahmad et al. (2008 ▶); Zia-ur-Rehman et al. (2005 ▶, 2006 ▶, 2007 ▶); Bihovsky et al. (2004 ▶); Braun (1923 ▶); Fabiola et al. (1998 ▶); Kojić-Prodić & Rużić-Toroš (1982 ▶); Lombardino et al. (1971 ▶); Turck et al. (1996 ▶); Weast et al. (1984 ▶).

Experimental

Crystal data

C13H13NO6S

M = 311.30

Orthorhombic,

a = 11.7982 (3) Å

b = 8.7206 (2) Å

c = 13.2474 (4) Å

V = 1362.99 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 120 (2) K

0.50 × 0.30 × 0.15 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.879, T max = 0.961

12553 measured reflections

3095 independent reflections

2849 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.100

S = 1.13

3095 reflections

194 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.64 e Å−3

Absolute structure: Flack (1983 ▶), 1466 Friedel pairs

Flack parameter: 0.00 (8)

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; 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 (Watkin et al., 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019156/bt2729sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019156/bt2729Isup2.hkl

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

C13H13NO6S	F000 = 648
Mr = 311.30	Dx = 1.517 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 6916 reflections
a = 11.7982 (3) Å	θ = 2.9–27.5º
b = 8.7206 (2) Å	µ = 0.27 mm−1
c = 13.2474 (4) Å	T = 120 (2) K
V = 1362.99 (6) Å3	Block, colourless
Z = 4	0.50 × 0.30 × 0.15 mm

Bruker–Nonius KappaCCD diffractometer	3095 independent reflections
Radiation source: Bruker Nonius FR591 Rotating Anode	2849 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
Detector resolution: 9.091 pixels mm-1	θmax = 27.5º
T = 120(2) K	θmin = 3.1º
φ and ω scans	h = −15→15
Absorption correction: multi-scan(SADABS; Sheldrick, 2007)	k = −11→11
Tmin = 0.879, Tmax = 0.961	l = −17→17
12553 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.0621P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.100	(Δ/σ)max < 0.001
S = 1.13	Δρmax = 0.57 e Å−3
3095 reflections	Δρmin = −0.64 e Å−3
194 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.067 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1466 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.00 (8)

Experimental. SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.6723 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
S1	0.12520 (4)	0.72682 (5)	0.71113 (5)	0.01779 (15)
O1	0.14000 (12)	0.85887 (19)	0.64793 (13)	0.0249 (4)
O2	0.21431 (12)	0.61542 (17)	0.71678 (14)	0.0255 (4)
O3	−0.19773 (12)	0.91805 (17)	0.77253 (12)	0.0204 (3)
H3	−0.2440	0.8985	0.7261	0.031*
O4	−0.27020 (12)	0.78295 (17)	0.61171 (13)	0.0229 (4)
O5	−0.15104 (13)	0.62248 (18)	0.53092 (12)	0.0234 (4)
O6	−0.03227 (14)	0.48788 (19)	0.85565 (13)	0.0287 (4)
N1	0.00988 (15)	0.63873 (19)	0.67500 (15)	0.0172 (4)
C1	0.08889 (18)	0.7943 (2)	0.83187 (17)	0.0173 (4)
C2	0.16859 (19)	0.8042 (3)	0.90839 (18)	0.0231 (5)
H2	0.2436	0.7675	0.8984	0.028*
C3	0.1371 (2)	0.8685 (3)	0.9994 (2)	0.0258 (5)
H3A	0.1909	0.8765	1.0525	0.031*
C4	0.0269 (2)	0.9218 (3)	1.01423 (18)	0.0244 (5)
H4	0.0061	0.9659	1.0771	0.029*
C5	−0.05253 (19)	0.9105 (2)	0.93717 (17)	0.0195 (4)
H5	−0.1274	0.9473	0.9476	0.023*
C6	−0.02314 (17)	0.8457 (2)	0.84476 (17)	0.0169 (4)
C7	−0.10643 (17)	0.8267 (2)	0.76334 (17)	0.0156 (4)
C8	−0.09225 (18)	0.7266 (2)	0.68505 (15)	0.0155 (4)
C9	−0.17931 (18)	0.7142 (2)	0.60656 (16)	0.0172 (4)
C10	−0.2356 (2)	0.6047 (3)	0.4522 (2)	0.0327 (6)
H10A	−0.3074	0.5716	0.4822	0.049*
H10B	−0.2098	0.5275	0.4035	0.049*
H10C	−0.2465	0.7029	0.4176	0.049*
C11	0.00404 (19)	0.4701 (2)	0.67907 (18)	0.0202 (4)
H11A	0.0763	0.4277	0.6532	0.024*
H11B	−0.0572	0.4350	0.6335	0.024*
C12	−0.01724 (18)	0.4058 (2)	0.78301 (19)	0.0216 (5)
C13	−0.0175 (2)	0.2338 (3)	0.7899 (2)	0.0329 (6)
H13A	−0.0154	0.2028	0.8609	0.049*
H13B	0.0492	0.1928	0.7549	0.049*
H13C	−0.0864	0.1935	0.7582	0.049*

	U11	U22	U33	U12	U13	U23
S1	0.0125 (2)	0.0212 (2)	0.0196 (2)	0.00081 (16)	0.0010 (2)	0.0031 (3)
O1	0.0198 (8)	0.0285 (8)	0.0263 (10)	−0.0038 (6)	0.0031 (6)	0.0092 (7)
O2	0.0170 (7)	0.0302 (8)	0.0293 (9)	0.0066 (5)	−0.0005 (7)	−0.0005 (8)
O3	0.0159 (7)	0.0222 (7)	0.0232 (8)	0.0050 (5)	−0.0035 (6)	−0.0042 (7)
O4	0.0176 (8)	0.0256 (7)	0.0256 (8)	0.0052 (6)	−0.0034 (6)	−0.0057 (7)
O5	0.0237 (9)	0.0267 (9)	0.0198 (8)	0.0058 (6)	−0.0048 (6)	−0.0056 (7)
O6	0.0361 (10)	0.0257 (8)	0.0243 (9)	0.0012 (7)	0.0043 (7)	0.0048 (7)
N1	0.0148 (9)	0.0162 (7)	0.0205 (9)	0.0014 (6)	0.0018 (7)	0.0003 (7)
C1	0.0173 (10)	0.0157 (8)	0.0190 (10)	−0.0019 (7)	0.0016 (9)	0.0019 (9)
C2	0.0164 (11)	0.0253 (10)	0.0276 (12)	−0.0014 (8)	−0.0053 (9)	0.0016 (10)
C3	0.0267 (13)	0.0267 (12)	0.0241 (12)	−0.0015 (9)	−0.0110 (9)	0.0007 (10)
C4	0.0310 (13)	0.0232 (10)	0.0191 (11)	0.0003 (9)	−0.0031 (9)	−0.0014 (9)
C5	0.0205 (11)	0.0158 (9)	0.0222 (10)	−0.0019 (7)	0.0009 (9)	0.0011 (9)
C6	0.0181 (11)	0.0119 (8)	0.0208 (11)	−0.0029 (7)	−0.0013 (8)	0.0036 (8)
C7	0.0129 (9)	0.0150 (9)	0.0188 (10)	−0.0008 (7)	0.0016 (8)	0.0030 (8)
C8	0.0137 (9)	0.0141 (9)	0.0188 (11)	−0.0009 (7)	0.0004 (8)	0.0021 (8)
C9	0.0161 (10)	0.0187 (9)	0.0168 (10)	−0.0009 (8)	0.0005 (8)	0.0004 (8)
C10	0.0323 (14)	0.0408 (12)	0.0250 (12)	0.0121 (11)	−0.0117 (10)	−0.0120 (12)
C11	0.0205 (10)	0.0168 (9)	0.0234 (11)	0.0035 (8)	−0.0005 (8)	−0.0019 (9)
C12	0.0144 (11)	0.0200 (10)	0.0303 (13)	0.0005 (7)	−0.0008 (9)	0.0035 (10)
C13	0.0332 (15)	0.0194 (11)	0.0460 (17)	0.0012 (9)	0.0037 (12)	0.0042 (11)

S1—O2	1.4335 (14)	C4—C5	1.389 (3)
S1—O1	1.4345 (17)	C4—H4	0.9500
S1—N1	1.6341 (19)	C5—C6	1.392 (3)
S1—C1	1.757 (2)	C5—H5	0.9500
O3—C7	1.345 (2)	C6—C7	1.469 (3)
O3—H3	0.8400	C7—C8	1.366 (3)
O4—C9	1.231 (3)	C8—C9	1.465 (3)
O5—C9	1.325 (3)	C10—H10A	0.9800
O5—C10	1.452 (3)	C10—H10B	0.9800
O6—C12	1.212 (3)	C10—H10C	0.9800
N1—C8	1.434 (3)	C11—C12	1.508 (3)
N1—C11	1.473 (3)	C11—H11A	0.9900
C1—C2	1.385 (3)	C11—H11B	0.9900
C1—C6	1.406 (3)	C12—C13	1.503 (3)
C2—C3	1.381 (4)	C13—H13A	0.9800
C2—H2	0.9500	C13—H13B	0.9800
C3—C4	1.394 (4)	C13—H13C	0.9800
C3—H3A	0.9500
O2—S1—O1	119.03 (10)	O3—C7—C6	113.72 (18)
O2—S1—N1	107.90 (9)	C8—C7—C6	123.24 (18)
O1—S1—N1	107.93 (10)	C7—C8—N1	120.98 (18)
O2—S1—C1	110.99 (11)	C7—C8—C9	119.99 (18)
O1—S1—C1	106.99 (10)	N1—C8—C9	118.93 (18)
N1—S1—C1	102.77 (10)	O4—C9—O5	123.7 (2)
C7—O3—H3	109.5	O4—C9—C8	122.39 (19)
C9—O5—C10	115.80 (17)	O5—C9—C8	113.86 (18)
C8—N1—C11	119.38 (17)	O5—C10—H10A	109.5
C8—N1—S1	114.92 (13)	O5—C10—H10B	109.5
C11—N1—S1	119.83 (15)	H10A—C10—H10B	109.5
C2—C1—C6	121.9 (2)	O5—C10—H10C	109.5
C2—C1—S1	121.44 (17)	H10A—C10—H10C	109.5
C6—C1—S1	116.52 (16)	H10B—C10—H10C	109.5
C3—C2—C1	118.8 (2)	N1—C11—C12	114.36 (18)
C3—C2—H2	120.6	N1—C11—H11A	108.7
C1—C2—H2	120.6	C12—C11—H11A	108.7
C2—C3—C4	120.6 (2)	N1—C11—H11B	108.7
C2—C3—H3A	119.7	C12—C11—H11B	108.7
C4—C3—H3A	119.7	H11A—C11—H11B	107.6
C5—C4—C3	120.1 (2)	O6—C12—C13	122.8 (2)
C5—C4—H4	119.9	O6—C12—C11	121.97 (18)
C3—C4—H4	119.9	C13—C12—C11	115.3 (2)
C6—C5—C4	120.4 (2)	C12—C13—H13A	109.5
C6—C5—H5	119.8	C12—C13—H13B	109.5
C4—C5—H5	119.8	H13A—C13—H13B	109.5
C5—C6—C1	118.06 (19)	C12—C13—H13C	109.5
C5—C6—C7	121.68 (19)	H13A—C13—H13C	109.5
C1—C6—C7	120.2 (2)	H13B—C13—H13C	109.5
O3—C7—C8	123.04 (19)
O2—S1—N1—C8	167.94 (15)	C5—C6—C7—O3	20.3 (3)
O1—S1—N1—C8	−62.23 (17)	C1—C6—C7—O3	−161.46 (18)
C1—S1—N1—C8	50.61 (17)	C5—C6—C7—C8	−160.21 (19)
O2—S1—N1—C11	15.1 (2)	C1—C6—C7—C8	18.0 (3)
O1—S1—N1—C11	144.91 (16)	O3—C7—C8—N1	175.91 (18)
C1—S1—N1—C11	−102.25 (17)	C6—C7—C8—N1	−3.5 (3)
O2—S1—C1—C2	31.3 (2)	O3—C7—C8—C9	−0.6 (3)
O1—S1—C1—C2	−100.01 (18)	C6—C7—C8—C9	−179.97 (18)
N1—S1—C1—C2	146.46 (18)	C11—N1—C8—C7	118.1 (2)
O2—S1—C1—C6	−152.25 (15)	S1—N1—C8—C7	−34.9 (2)
O1—S1—C1—C6	76.41 (16)	C11—N1—C8—C9	−65.4 (3)
N1—S1—C1—C6	−37.13 (17)	S1—N1—C8—C9	141.61 (16)
C6—C1—C2—C3	−0.9 (3)	C10—O5—C9—O4	−0.7 (3)
S1—C1—C2—C3	175.34 (17)	C10—O5—C9—C8	179.00 (18)
C1—C2—C3—C4	0.3 (3)	C7—C8—C9—O4	−5.5 (3)
C2—C3—C4—C5	0.1 (3)	N1—C8—C9—O4	177.96 (18)
C3—C4—C5—C6	0.2 (3)	C7—C8—C9—O5	174.79 (18)
C4—C5—C6—C1	−0.7 (3)	N1—C8—C9—O5	−1.8 (3)
C4—C5—C6—C7	177.53 (19)	C8—N1—C11—C12	−73.3 (3)
C2—C1—C6—C5	1.1 (3)	S1—N1—C11—C12	78.4 (2)
S1—C1—C6—C5	−175.30 (15)	N1—C11—C12—O6	2.6 (3)
C2—C1—C6—C7	−177.19 (19)	N1—C11—C12—C13	−176.96 (19)
S1—C1—C6—C7	6.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.84	1.85	2.580 (2)	145
C3—H3A···O1i	0.95	2.37	3.286 (3)	163
C4—H4···O1ii	0.95	2.49	3.267 (3)	139
C11—H11A···O2	0.99	2.46	2.830 (3)	102
C11—H11B···O5	0.99	2.40	2.994 (3)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4	0.84	1.85	2.580 (2)	145
C3—H3A⋯O1i	0.95	2.37	3.286 (3)	163
C4—H4⋯O1ii	0.95	2.49	3.267 (3)	139
C11—H11A⋯O2	0.99	2.46	2.830 (3)	102
C11—H11B⋯O5	0.99	2.40	2.994 (3)	118

Symmetry codes: (i) ; (ii) .