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

In the crystal structure of the title compound, C(13)H(15)NO(5)S, the mol-ecules exhibit weak S=O⋯H-C and C=O⋯H-C inter-molecular inter-actions and arrange themselves into centrosymmetric dimers by means of π-π inter-actions (ring centroids are separated by 3.619 Å, while the closest C⋯C contacts are 3.514 Å). 1,2-Benzothia-zines of this kind have a range of biological activities and are used as medicines in the treatment of inflammation and rheumatoid arthritis.

Related literature

For related literature on benzothia­zines, see: Ahmad et al. (2008 ▶); Bihovsky et al. (2004 ▶); Fabiola et al. (1998 ▶); Golič et al. (1987 ▶); Kojić-Prodić & Rużić-Toroš (1982 ▶); Lombardino et al. (1971 ▶); Reck et al. (1988 ▶); Zia-ur-Rehman et al. (2005 ▶, 2006 ▶, 2007 ▶).

Experimental

Crystal data

C13H15NO5S

M = 297.32

Triclinic,

a = 7.9810 (4) Å

b = 8.1215 (4) Å

c = 10.8173 (6) Å

α = 89.4783 (7)°

β = 79.5124 (8)°

γ = 79.3434 (7)°

V = 677.33 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 150 (2) K

0.57 × 0.17 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.867, T max = 0.975

8153 measured reflections

4069 independent reflections

3678 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.096

S = 1.07

4069 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021363/bt2743sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021363/bt2743Isup2.hkl

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

C13H15NO5S	Z = 2
Mr = 297.32	F000 = 312
Triclinic, P1	Dx = 1.458 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.9810 (4) Å	Cell parameters from 4878 reflections
b = 8.1215 (4) Å	θ = 2.6–30.5º
c = 10.8173 (6) Å	µ = 0.26 mm−1
α = 89.4783 (7)º	T = 150 (2) K
β = 79.5124 (8)º	Block, colourless
γ = 79.3434 (7)º	0.57 × 0.17 × 0.10 mm
V = 677.33 (6) Å3

Bruker APEXII CCD diffractometer	4069 independent reflections
Radiation source: fine-focus sealed tube	3678 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.014
T = 150(2) K	θmax = 30.6º
ω rotation with narrow frames scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 2007)	h = −11→11
Tmin = 0.867, Tmax = 0.975	k = −11→11
8153 measured reflections	l = −15→15

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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0555P)2 + 0.1549P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
4069 reflections	Δρmax = 0.47 e Å−3
184 parameters	Δρmin = −0.34 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N1	0.37350 (11)	0.28852 (10)	0.19858 (8)	0.01854 (16)
C11	0.32384 (14)	0.38127 (14)	0.08880 (10)	0.0245 (2)
H11A	0.4141	0.3475	0.0145	0.037*
H11B	0.3107	0.5019	0.1052	0.037*
H11C	0.2137	0.3560	0.0738	0.037*
S1	0.24645 (3)	0.32872 (3)	0.33583 (2)	0.02022 (8)
O1	0.34949 (12)	0.28319 (11)	0.43054 (8)	0.02893 (18)
O2	0.15077 (12)	0.49632 (10)	0.33569 (9)	0.0320 (2)
C1	0.10979 (13)	0.18357 (12)	0.33574 (9)	0.01836 (18)
C2	−0.06595 (13)	0.22200 (14)	0.38733 (10)	0.0230 (2)
H2	−0.1177	0.3311	0.4207	0.028*
C3	−0.16426 (14)	0.09717 (16)	0.38904 (10)	0.0268 (2)
H3	−0.2851	0.1213	0.4223	0.032*
C4	−0.08623 (15)	−0.06293 (15)	0.34218 (10)	0.0259 (2)
H4	−0.1538	−0.1483	0.3463	0.031*
C5	0.08906 (14)	−0.09988 (13)	0.28949 (10)	0.02141 (19)
H5	0.1406	−0.2099	0.2580	0.026*
C6	0.18987 (12)	0.02506 (12)	0.28280 (9)	0.01735 (17)
C7	0.37251 (12)	−0.00786 (12)	0.21908 (9)	0.01697 (17)
O3	0.45163 (10)	−0.17111 (9)	0.19875 (7)	0.02058 (15)
C12	0.49827 (15)	−0.25298 (13)	0.31109 (10)	0.0239 (2)
H12A	0.3954	−0.2867	0.3633	0.029*
H12B	0.5423	−0.1753	0.3617	0.029*
C13	0.63614 (18)	−0.40461 (15)	0.27026 (14)	0.0356 (3)
H13A	0.5911	−0.4810	0.2207	0.053*
H13B	0.6698	−0.4619	0.3446	0.053*
H13C	0.7375	−0.3699	0.2189	0.053*
C8	0.45807 (12)	0.11773 (12)	0.17707 (9)	0.01727 (17)
C9	0.64295 (13)	0.08859 (13)	0.11182 (9)	0.01947 (18)
O4	0.72988 (11)	−0.04393 (11)	0.07302 (9)	0.0333 (2)
O5	0.70186 (10)	0.23360 (10)	0.10291 (8)	0.02397 (16)
C10	0.88320 (14)	0.21929 (15)	0.04958 (11)	0.0264 (2)
H10A	0.9526	0.1425	0.0994	0.040*
H10B	0.9156	0.3299	0.0503	0.040*
H10C	0.9047	0.1758	−0.0372	0.040*

	U11	U22	U33	U12	U13	U23
N1	0.0194 (4)	0.0142 (3)	0.0198 (4)	−0.0011 (3)	0.0003 (3)	0.0009 (3)
C11	0.0246 (5)	0.0219 (5)	0.0254 (5)	−0.0017 (4)	−0.0033 (4)	0.0062 (4)
S1	0.02258 (13)	0.01530 (12)	0.02126 (13)	−0.00367 (9)	0.00029 (9)	−0.00292 (8)
O1	0.0339 (4)	0.0336 (4)	0.0221 (4)	−0.0119 (3)	−0.0065 (3)	−0.0039 (3)
O2	0.0330 (4)	0.0152 (4)	0.0405 (5)	−0.0009 (3)	0.0084 (4)	−0.0039 (3)
C1	0.0194 (4)	0.0180 (4)	0.0173 (4)	−0.0033 (3)	−0.0025 (3)	0.0017 (3)
C2	0.0203 (4)	0.0257 (5)	0.0204 (4)	−0.0009 (4)	−0.0006 (4)	0.0008 (4)
C3	0.0194 (4)	0.0379 (6)	0.0230 (5)	−0.0080 (4)	−0.0015 (4)	0.0020 (4)
C4	0.0243 (5)	0.0325 (5)	0.0246 (5)	−0.0137 (4)	−0.0058 (4)	0.0048 (4)
C5	0.0241 (5)	0.0204 (4)	0.0219 (4)	−0.0074 (4)	−0.0067 (4)	0.0027 (4)
C6	0.0184 (4)	0.0171 (4)	0.0169 (4)	−0.0035 (3)	−0.0039 (3)	0.0019 (3)
C7	0.0189 (4)	0.0143 (4)	0.0175 (4)	−0.0017 (3)	−0.0041 (3)	−0.0008 (3)
O3	0.0266 (4)	0.0134 (3)	0.0204 (3)	−0.0003 (3)	−0.0040 (3)	−0.0010 (2)
C12	0.0284 (5)	0.0179 (4)	0.0251 (5)	0.0011 (4)	−0.0094 (4)	0.0004 (4)
C13	0.0396 (7)	0.0210 (5)	0.0446 (7)	0.0095 (5)	−0.0183 (6)	−0.0072 (5)
C8	0.0171 (4)	0.0153 (4)	0.0185 (4)	−0.0014 (3)	−0.0023 (3)	−0.0010 (3)
C9	0.0186 (4)	0.0202 (4)	0.0190 (4)	−0.0033 (3)	−0.0022 (3)	−0.0012 (3)
O4	0.0237 (4)	0.0231 (4)	0.0472 (5)	−0.0014 (3)	0.0062 (4)	−0.0086 (4)
O5	0.0175 (3)	0.0207 (3)	0.0323 (4)	−0.0045 (3)	0.0003 (3)	−0.0009 (3)
C10	0.0176 (4)	0.0304 (5)	0.0299 (5)	−0.0059 (4)	0.0002 (4)	0.0026 (4)

N1—C8	1.4270 (12)	C5—H5	0.9500
N1—C11	1.4762 (13)	C6—C7	1.4713 (13)
N1—S1	1.6363 (9)	C7—C8	1.3599 (13)
C11—H11A	0.9800	C7—O3	1.3602 (11)
C11—H11B	0.9800	O3—C12	1.4546 (12)
C11—H11C	0.9800	C12—C13	1.5014 (15)
S1—O1	1.4318 (9)	C12—H12A	0.9900
S1—O2	1.4324 (8)	C12—H12B	0.9900
S1—C1	1.7479 (10)	C13—H13A	0.9800
C1—C2	1.3901 (14)	C13—H13B	0.9800
C1—C6	1.4035 (13)	C13—H13C	0.9800
C2—C3	1.3900 (16)	C8—C9	1.4920 (13)
C2—H2	0.9500	C9—O4	1.2008 (13)
C3—C4	1.3904 (17)	C9—O5	1.3429 (12)
C3—H3	0.9500	O5—C10	1.4409 (12)
C4—C5	1.3891 (15)	C10—H10A	0.9800
C4—H4	0.9500	C10—H10B	0.9800
C5—C6	1.4006 (14)	C10—H10C	0.9800
C8—N1—C11	116.99 (8)	C5—C6—C7	120.92 (9)
C8—N1—S1	114.71 (6)	C1—C6—C7	121.18 (9)
C11—N1—S1	118.75 (7)	C8—C7—O3	120.74 (9)
N1—C11—H11A	109.5	C8—C7—C6	122.18 (9)
N1—C11—H11B	109.5	O3—C7—C6	117.02 (8)
H11A—C11—H11B	109.5	C7—O3—C12	113.59 (7)
N1—C11—H11C	109.5	O3—C12—C13	107.98 (9)
H11A—C11—H11C	109.5	O3—C12—H12A	110.1
H11B—C11—H11C	109.5	C13—C12—H12A	110.1
O1—S1—O2	119.30 (6)	O3—C12—H12B	110.1
O1—S1—N1	107.81 (5)	C13—C12—H12B	110.1
O2—S1—N1	108.08 (5)	H12A—C12—H12B	108.4
O1—S1—C1	108.19 (5)	C12—C13—H13A	109.5
O2—S1—C1	110.56 (5)	C12—C13—H13B	109.5
N1—S1—C1	101.38 (5)	H13A—C13—H13B	109.5
C2—C1—C6	122.35 (9)	C12—C13—H13C	109.5
C2—C1—S1	122.00 (8)	H13A—C13—H13C	109.5
C6—C1—S1	115.63 (7)	H13B—C13—H13C	109.5
C3—C2—C1	118.52 (10)	C7—C8—N1	120.24 (9)
C3—C2—H2	120.7	C7—C8—C9	123.51 (9)
C1—C2—H2	120.7	N1—C8—C9	116.22 (8)
C2—C3—C4	120.16 (10)	O4—C9—O5	123.71 (9)
C2—C3—H3	119.9	O4—C9—C8	126.14 (9)
C4—C3—H3	119.9	O5—C9—C8	110.15 (8)
C5—C4—C3	120.97 (10)	C9—O5—C10	115.19 (8)
C5—C4—H4	119.5	O5—C10—H10A	109.5
C3—C4—H4	119.5	O5—C10—H10B	109.5
C4—C5—C6	120.01 (10)	H10A—C10—H10B	109.5
C4—C5—H5	120.0	O5—C10—H10C	109.5
C6—C5—H5	120.0	H10A—C10—H10C	109.5
C5—C6—C1	117.87 (9)	H10B—C10—H10C	109.5
C8—N1—S1—O1	58.91 (8)	S1—C1—C6—C7	−6.73 (12)
C11—N1—S1—O1	−155.79 (8)	C5—C6—C7—C8	159.51 (10)
C8—N1—S1—O2	−170.89 (7)	C1—C6—C7—C8	−18.73 (14)
C11—N1—S1—O2	−25.58 (9)	C5—C6—C7—O3	−17.78 (13)
C8—N1—S1—C1	−54.62 (8)	C1—C6—C7—O3	163.98 (9)
C11—N1—S1—C1	90.69 (8)	C8—C7—O3—C12	106.82 (11)
O1—S1—C1—C2	104.51 (9)	C6—C7—O3—C12	−75.85 (11)
O2—S1—C1—C2	−27.82 (10)	C7—O3—C12—C13	−159.92 (9)
N1—S1—C1—C2	−142.26 (9)	O3—C7—C8—N1	179.78 (8)
O1—S1—C1—C6	−74.15 (9)	C6—C7—C8—N1	2.59 (14)
O2—S1—C1—C6	153.53 (8)	O3—C7—C8—C9	−2.63 (15)
N1—S1—C1—C6	39.09 (8)	C6—C7—C8—C9	−179.82 (9)
C6—C1—C2—C3	1.63 (15)	C11—N1—C8—C7	−107.70 (11)
S1—C1—C2—C3	−176.93 (8)	S1—N1—C8—C7	38.24 (12)
C1—C2—C3—C4	1.25 (16)	C11—N1—C8—C9	74.55 (11)
C2—C3—C4—C5	−2.02 (17)	S1—N1—C8—C9	−139.52 (8)
C3—C4—C5—C6	−0.10 (16)	C7—C8—C9—O4	11.14 (17)
C4—C5—C6—C1	2.85 (15)	N1—C8—C9—O4	−171.18 (10)
C4—C5—C6—C7	−175.45 (9)	C7—C8—C9—O5	−168.23 (9)
C2—C1—C6—C5	−3.67 (15)	N1—C8—C9—O5	9.45 (12)
S1—C1—C6—C5	174.98 (7)	O4—C9—O5—C10	−3.71 (15)
C2—C1—C6—C7	174.62 (9)	C8—C9—O5—C10	175.68 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.95	2.51	3.2726 (13)	137
C13—H13A···O5i	0.98	2.58	3.3715 (15)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.95	2.51	3.2726 (13)	137
C13—H13A⋯O5i	0.98	2.58	3.3715 (15)	138

Symmetry code: (i) .