Methyl 4-acet-oxy-2-methyl-2H-1,2-benzothia-zine-3-carboxyl-ate 1,1-dioxide.

In the title compound, C(13)H(13)NO(6)S, the thia-zine ring adopts a distorted half-chair conformation. Each mol-ecule is linked to its neighbour through inter-molecular C-H⋯O hydrogen bonds.

Related literature

For related literature, see: Fabiola et al. (1998 ▶); Golič & Leban (1987 ▶); Kojić-Prodić & Rużić-Toroš (1982 ▶); Rajagopal & Seshadri (1990 ▶); Reck et al. (1988 ▶); Rehman et al. (2005 ▶, 2006 ▶); Turck et al. (1996 ▶).

Experimental

Crystal data

C13H13NO6S

M = 311.30

Monoclinic,

a = 6.8917 (5) Å

b = 24.1814 (17) Å

c = 8.2861 (5) Å

β = 97.876 (4)°

V = 1367.86 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 120 (2) K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.902, T max = 0.949

12265 measured reflections

3032 independent reflections

2183 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.145

S = 1.03

3032 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.55 e Å−3

Data collection: COLLECT (Nonius, 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 (Pearce & Watkin, 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004029/kp2156sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004029/kp2156Isup2.hkl

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

C13H13NO6S	F(000) = 648
Mr = 311.30	Dx = 1.512 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15145 reflections
a = 6.8917 (5) Å	θ = 2.9–27.5°
b = 24.1814 (17) Å	µ = 0.26 mm−1
c = 8.2861 (5) Å	T = 120 K
β = 97.876 (4)°	Block, colourless
V = 1367.86 (16) Å3	0.40 × 0.20 × 0.20 mm
Z = 4

Bruker Nonius CCD camera on κ-goniostat diffractometer	3032 independent reflections
Radiation source: Bruker Nonius FR591 Rotating Anode	2183 reflections with I > 2σ(I)
graphite	Rint = 0.057
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans to fill the asymmetric unit	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −31→30
Tmin = 0.902, Tmax = 0.949	l = −10→9
12265 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0764P)2 + 0.6225P] where P = (Fo2 + 2Fc2)/3
3032 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.55 e Å−3

Experimental. SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.6195 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	0.5172 (4)	0.43090 (10)	0.7387 (3)	0.0183 (5)
C2	0.7043 (4)	0.45347 (10)	0.7686 (3)	0.0213 (6)
H2	0.7629	0.4616	0.8766	0.026*
C3	0.8032 (4)	0.46376 (10)	0.6369 (3)	0.0213 (5)
H3	0.9315	0.4790	0.6544	0.026*
C4	0.7153 (4)	0.45192 (10)	0.4788 (3)	0.0219 (6)
H4	0.7836	0.4597	0.3893	0.026*
C5	0.5299 (4)	0.42895 (9)	0.4508 (3)	0.0183 (5)
H5	0.4719	0.4211	0.3425	0.022*
C6	0.4276 (4)	0.41729 (9)	0.5809 (3)	0.0167 (5)
C7	0.2364 (3)	0.39001 (9)	0.5570 (3)	0.0162 (5)
C8	0.1613 (4)	0.36162 (10)	0.6749 (3)	0.0181 (5)
C9	−0.0253 (4)	0.32911 (10)	0.6577 (3)	0.0202 (6)
C10	−0.2808 (4)	0.28845 (11)	0.4788 (3)	0.0301 (6)
H10A	−0.2544	0.2510	0.5215	0.045*
H10B	−0.3298	0.2865	0.3622	0.045*
H10C	−0.3793	0.3061	0.5364	0.045*
C11	0.3594 (4)	0.30948 (11)	0.8954 (3)	0.0294 (7)
H11A	0.2711	0.2784	0.8643	0.044*
H11B	0.3914	0.3107	1.0143	0.044*
H11C	0.4800	0.3048	0.8464	0.044*
C12	0.1291 (4)	0.35858 (10)	0.2862 (3)	0.0207 (6)
C13	−0.0222 (4)	0.37189 (12)	0.1456 (3)	0.0307 (7)
H13A	−0.0128	0.3455	0.0572	0.046*
H13B	−0.0008	0.4094	0.1073	0.046*
H13C	−0.1526	0.3695	0.1796	0.046*
N1	0.2622 (3)	0.36187 (8)	0.8366 (2)	0.0185 (5)
O1	0.4912 (3)	0.41115 (8)	1.04687 (19)	0.0263 (4)
O2	0.2249 (3)	0.46261 (7)	0.8823 (2)	0.0234 (4)
O3	0.1272 (2)	0.39845 (6)	0.40526 (18)	0.0184 (4)
O4	−0.0967 (3)	0.31203 (8)	0.7727 (2)	0.0353 (5)
O5	−0.1014 (3)	0.32064 (7)	0.5028 (2)	0.0266 (4)
O6	0.2420 (3)	0.32061 (7)	0.3014 (2)	0.0282 (5)
S1	0.37225 (9)	0.42031 (2)	0.89441 (7)	0.0197 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0191 (13)	0.0190 (12)	0.0169 (12)	0.0010 (10)	0.0030 (10)	0.0017 (9)
C2	0.0201 (14)	0.0197 (12)	0.0222 (13)	−0.0006 (10)	−0.0035 (10)	−0.0003 (10)
C3	0.0138 (13)	0.0196 (12)	0.0302 (14)	−0.0010 (10)	0.0021 (10)	0.0026 (11)
C4	0.0205 (14)	0.0207 (12)	0.0260 (13)	0.0023 (10)	0.0082 (10)	0.0032 (10)
C5	0.0193 (14)	0.0183 (12)	0.0175 (12)	0.0029 (10)	0.0034 (10)	0.0009 (9)
C6	0.0162 (13)	0.0149 (11)	0.0182 (12)	0.0021 (9)	−0.0003 (10)	0.0017 (9)
C7	0.0146 (12)	0.0198 (12)	0.0135 (11)	0.0019 (10)	−0.0006 (9)	−0.0019 (9)
C8	0.0204 (14)	0.0183 (12)	0.0151 (11)	0.0004 (10)	0.0009 (9)	−0.0017 (9)
C9	0.0214 (14)	0.0197 (12)	0.0201 (13)	0.0000 (10)	0.0047 (10)	−0.0040 (10)
C10	0.0250 (16)	0.0325 (15)	0.0320 (15)	−0.0132 (12)	0.0013 (12)	−0.0068 (12)
C11	0.0372 (17)	0.0243 (14)	0.0257 (14)	0.0046 (12)	0.0006 (12)	0.0038 (11)
C12	0.0186 (14)	0.0267 (13)	0.0175 (12)	−0.0040 (11)	0.0046 (10)	−0.0015 (10)
C13	0.0280 (16)	0.0437 (17)	0.0190 (13)	−0.0027 (13)	−0.0015 (11)	−0.0039 (12)
N1	0.0192 (12)	0.0202 (10)	0.0157 (10)	−0.0012 (8)	0.0013 (8)	0.0007 (8)
O1	0.0243 (11)	0.0390 (11)	0.0141 (9)	−0.0034 (8)	−0.0023 (7)	0.0010 (8)
O2	0.0248 (10)	0.0230 (9)	0.0223 (9)	0.0011 (7)	0.0031 (7)	−0.0041 (7)
O3	0.0176 (9)	0.0218 (9)	0.0152 (8)	0.0003 (7)	−0.0003 (7)	−0.0008 (7)
O4	0.0386 (13)	0.0458 (12)	0.0225 (10)	−0.0196 (10)	0.0080 (9)	0.0008 (9)
O5	0.0222 (10)	0.0351 (10)	0.0223 (9)	−0.0119 (8)	0.0020 (7)	−0.0044 (8)
O6	0.0308 (11)	0.0284 (10)	0.0259 (10)	0.0028 (8)	0.0054 (8)	−0.0049 (8)
S1	0.0207 (4)	0.0234 (3)	0.0147 (3)	−0.0017 (2)	0.0014 (2)	−0.0012 (2)

C1—C2	1.391 (3)	C10—O5	1.451 (3)
C1—C6	1.407 (3)	C10—H10A	0.9800
C1—S1	1.755 (3)	C10—H10B	0.9800
C2—C3	1.386 (4)	C10—H10C	0.9800
C2—H2	0.9500	C11—N1	1.484 (3)
C3—C4	1.396 (3)	C11—H11A	0.9800
C3—H3	0.9500	C11—H11B	0.9800
C4—C5	1.384 (3)	C11—H11C	0.9800
C4—H4	0.9500	C12—O6	1.199 (3)
C5—C6	1.396 (3)	C12—O3	1.380 (3)
C5—H5	0.9500	C12—C13	1.488 (3)
C6—C7	1.463 (3)	C13—H13A	0.9800
C7—C8	1.353 (3)	C13—H13B	0.9800
C7—O3	1.389 (3)	C13—H13C	0.9800
C8—N1	1.422 (3)	N1—S1	1.644 (2)
C8—C9	1.498 (3)	O1—S1	1.4258 (17)
C9—O4	1.203 (3)	O2—S1	1.4354 (18)
C9—O5	1.334 (3)
C2—C1—C6	122.4 (2)	O5—C10—H10C	109.5
C2—C1—S1	122.25 (18)	H10A—C10—H10C	109.5
C6—C1—S1	115.33 (18)	H10B—C10—H10C	109.5
C3—C2—C1	118.3 (2)	N1—C11—H11A	109.5
C3—C2—H2	120.8	N1—C11—H11B	109.5
C1—C2—H2	120.8	H11A—C11—H11B	109.5
C2—C3—C4	120.4 (2)	N1—C11—H11C	109.5
C2—C3—H3	119.8	H11A—C11—H11C	109.5
C4—C3—H3	119.8	H11B—C11—H11C	109.5
C5—C4—C3	120.8 (2)	O6—C12—O3	121.9 (2)
C5—C4—H4	119.6	O6—C12—C13	128.5 (2)
C3—C4—H4	119.6	O3—C12—C13	109.5 (2)
C4—C5—C6	120.3 (2)	C12—C13—H13A	109.5
C4—C5—H5	119.9	C12—C13—H13B	109.5
C6—C5—H5	119.9	H13A—C13—H13B	109.5
C5—C6—C1	117.9 (2)	C12—C13—H13C	109.5
C5—C6—C7	121.9 (2)	H13A—C13—H13C	109.5
C1—C6—C7	120.2 (2)	H13B—C13—H13C	109.5
C8—C7—O3	121.0 (2)	C8—N1—C11	116.50 (18)
C8—C7—C6	123.9 (2)	C8—N1—S1	115.14 (15)
O3—C7—C6	114.97 (19)	C11—N1—S1	117.95 (17)
C7—C8—N1	119.5 (2)	C12—O3—C7	119.17 (18)
C7—C8—C9	127.3 (2)	C9—O5—C10	115.4 (2)
N1—C8—C9	113.2 (2)	O1—S1—O2	119.20 (10)
O4—C9—O5	124.0 (2)	O1—S1—N1	108.13 (11)
O4—C9—C8	123.0 (2)	O2—S1—N1	107.37 (10)
O5—C9—C8	113.0 (2)	O1—S1—C1	110.97 (12)
O5—C10—H10A	109.5	O2—S1—C1	108.25 (11)
O5—C10—H10B	109.5	N1—S1—C1	101.39 (11)
H10A—C10—H10B	109.5
C6—C1—C2—C3	1.3 (4)	C7—C8—N1—C11	−108.8 (3)
S1—C1—C2—C3	−175.79 (18)	C9—C8—N1—C11	72.3 (3)
C1—C2—C3—C4	0.4 (4)	C7—C8—N1—S1	35.6 (3)
C2—C3—C4—C5	−1.1 (4)	C9—C8—N1—S1	−143.34 (17)
C3—C4—C5—C6	0.1 (4)	O6—C12—O3—C7	−10.5 (3)
C4—C5—C6—C1	1.6 (3)	C13—C12—O3—C7	170.6 (2)
C4—C5—C6—C7	−176.3 (2)	C8—C7—O3—C12	−86.4 (3)
C2—C1—C6—C5	−2.3 (3)	C6—C7—O3—C12	98.0 (2)
S1—C1—C6—C5	175.01 (17)	O4—C9—O5—C10	−0.2 (4)
C2—C1—C6—C7	175.6 (2)	C8—C9—O5—C10	178.9 (2)
S1—C1—C6—C7	−7.1 (3)	C8—N1—S1—O1	−170.76 (17)
C5—C6—C7—C8	157.1 (2)	C11—N1—S1—O1	−27.0 (2)
C1—C6—C7—C8	−20.7 (4)	C8—N1—S1—O2	59.42 (19)
C5—C6—C7—O3	−27.4 (3)	C11—N1—S1—O2	−156.78 (18)
C1—C6—C7—O3	154.8 (2)	C8—N1—S1—C1	−54.01 (19)
O3—C7—C8—N1	−169.13 (19)	C11—N1—S1—C1	89.79 (19)
C6—C7—C8—N1	6.2 (4)	C2—C1—S1—O1	−28.5 (2)
O3—C7—C8—C9	9.6 (4)	C6—C1—S1—O1	154.23 (17)
C6—C7—C8—C9	−175.1 (2)	C2—C1—S1—O2	104.1 (2)
C7—C8—C9—O4	−168.4 (3)	C6—C1—S1—O2	−73.2 (2)
N1—C8—C9—O4	10.4 (3)	C2—C1—S1—N1	−143.1 (2)
C7—C8—C9—O5	12.4 (4)	C6—C1—S1—N1	39.6 (2)
N1—C8—C9—O5	−168.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O4i	0.98	2.49	3.387 (3)	153
C5—H5···O1i	0.95	2.48	3.349 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O4i	0.98	2.48	3.387 (3)	153
C5—H5⋯O1i	0.95	2.48	3.349 (3)	151

Symmetry code: (i) .