1-Ethyl-1H-2,1-benzothia-zin-4(3H)-one 2,2-dioxide.

In the title compound, C(10)H(11)NO(3)S, there is distorted tetra-hedral geometry around the S atom. The heterocyclic thia-zine ring adopts a half-chair conformation. The ethyl and sulfonyl groups form dihedral angles of 82.53 (13) and 88.91 (9)°, respectively, with the plane formed by the benzothia-zine ring, excluding the S atom; the S atom and the ethyl group lie on opposite sides of the ring. The mol-ecules are linked into dimers by inter-molecular C-H⋯O hydrogen bonds involving benzene C-H and carbonyl O atoms, thus forming eight-membered rings. The dimers are linked into chains via inter-actions of a similar type. There is an intra-molecular C-H⋯O hydrogen bond.

Related literature

For related literature, see: Hanson et al. (1999 ▶); Misu & Togo (2003 ▶); Shafiq et al. (2008 ▶); Siddique et al. (2006 ▶); Siddiqui et al. (2007 ▶); Tahir et al. (2008 ▶); Cremer & Pople (1975 ▶).

Experimental

Crystal data

C10H11NO3S

M = 225.26

Triclinic,

a = 7.0272 (3) Å

b = 8.0448 (4) Å

c = 9.5880 (4) Å

α = 99.124 (3)°

β = 95.075 (3)°

γ = 104.092 (3)°

V = 514.48 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 296 (2) K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.965, T max = 0.988

11339 measured reflections

2608 independent reflections

1760 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.107

S = 1.02

2608 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); 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 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003504/pv2067sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003504/pv2067Isup2.hkl

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

C10H11NO3S	Z = 2
Mr = 225.26	F000 = 236
Triclinic, P1	Dx = 1.454 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.0272 (3) Å	Cell parameters from 1760 reflections
b = 8.0448 (4) Å	θ = 2.2–28.7º
c = 9.5880 (4) Å	µ = 0.30 mm−1
α = 99.124 (3)º	T = 296 (2) K
β = 95.075 (3)º	Prismatic, colourless
γ = 104.092 (3)º	0.15 × 0.12 × 0.10 mm
V = 514.48 (4) Å3

Bruker Kappa APEXII CCD diffractometer	2608 independent reflections
Radiation source: fine-focus sealed tube	1760 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.036
Detector resolution: 7.40 pixels mm-1	θmax = 28.7º
T = 296(2) K	θmin = 2.2º
ω scans	h = −9→9
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −10→10
Tmin = 0.965, Tmax = 0.988	l = −12→12
11339 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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0488P)2 + 0.0854P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2608 reflections	Δρmax = 0.29 e Å−3
136 parameters	Δρmin = −0.26 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
S1	0.32887 (8)	0.16467 (6)	0.90938 (5)	0.04169 (17)
O1	0.5349 (2)	0.18066 (19)	0.90570 (14)	0.0531 (4)
O2	0.2664 (3)	0.2196 (2)	1.04236 (14)	0.0670 (5)
O3	0.2248 (2)	−0.25167 (19)	0.63616 (17)	0.0632 (4)
N1	0.2390 (2)	0.2638 (2)	0.79263 (15)	0.0415 (4)
C1	0.2558 (3)	0.2075 (2)	0.64688 (17)	0.0328 (4)
C2	0.2726 (3)	0.3249 (3)	0.5533 (2)	0.0429 (5)
H2	0.2746	0.4406	0.5861	0.051*
C3	0.2864 (3)	0.2688 (3)	0.4118 (2)	0.0489 (5)
H3	0.2959	0.3475	0.3498	0.059*
C4	0.2862 (3)	0.1000 (3)	0.3604 (2)	0.0485 (5)
H4	0.2982	0.0651	0.2651	0.058*
C5	0.2684 (3)	−0.0161 (3)	0.45077 (19)	0.0420 (5)
H5	0.2679	−0.1310	0.4160	0.050*
C6	0.2509 (2)	0.0337 (2)	0.59449 (17)	0.0329 (4)
C7	0.2276 (3)	−0.1022 (2)	0.6829 (2)	0.0389 (4)
C8	0.2024 (3)	−0.0522 (3)	0.8374 (2)	0.0445 (5)
H8A	0.2512	−0.1285	0.8919	0.053*
H8B	0.0627	−0.0687	0.8454	0.053*
C9	0.2066 (3)	0.4367 (3)	0.8431 (2)	0.0461 (5)
H9A	0.2951	0.5239	0.8032	0.055*
H9B	0.2378	0.4664	0.9461	0.055*
C10	−0.0036 (3)	0.4394 (3)	0.8011 (3)	0.0575 (6)
H10A	−0.0197	0.5532	0.8354	0.086*
H10B	−0.0914	0.3545	0.8420	0.086*
H10C	−0.0341	0.4120	0.6992	0.086*

	U11	U22	U33	U12	U13	U23
S1	0.0517 (3)	0.0444 (3)	0.0303 (2)	0.0137 (2)	0.00127 (19)	0.01149 (19)
O1	0.0444 (9)	0.0558 (9)	0.0541 (8)	0.0071 (7)	−0.0081 (6)	0.0135 (7)
O2	0.0971 (13)	0.0800 (12)	0.0318 (7)	0.0339 (10)	0.0142 (8)	0.0136 (7)
O3	0.0782 (12)	0.0343 (9)	0.0810 (11)	0.0192 (8)	0.0145 (9)	0.0127 (7)
N1	0.0633 (11)	0.0387 (9)	0.0299 (7)	0.0260 (8)	0.0075 (7)	0.0082 (6)
C1	0.0347 (10)	0.0366 (10)	0.0302 (8)	0.0141 (8)	0.0044 (7)	0.0083 (7)
C2	0.0504 (12)	0.0408 (11)	0.0434 (10)	0.0167 (9)	0.0083 (9)	0.0163 (8)
C3	0.0492 (13)	0.0673 (15)	0.0394 (10)	0.0197 (11)	0.0106 (9)	0.0273 (10)
C4	0.0436 (12)	0.0748 (16)	0.0305 (9)	0.0224 (10)	0.0055 (8)	0.0083 (9)
C5	0.0374 (11)	0.0459 (12)	0.0407 (10)	0.0152 (9)	0.0000 (8)	−0.0022 (8)
C6	0.0297 (9)	0.0366 (11)	0.0337 (9)	0.0118 (8)	0.0026 (7)	0.0066 (7)
C7	0.0332 (10)	0.0337 (11)	0.0498 (11)	0.0092 (8)	0.0013 (8)	0.0095 (8)
C8	0.0446 (12)	0.0431 (12)	0.0485 (11)	0.0080 (9)	0.0024 (9)	0.0237 (9)
C9	0.0618 (14)	0.0334 (11)	0.0423 (10)	0.0152 (10)	0.0087 (9)	−0.0004 (8)
C10	0.0615 (15)	0.0474 (14)	0.0693 (14)	0.0239 (11)	0.0180 (11)	0.0075 (11)

S1—O2	1.4244 (14)	C4—H4	0.9300
S1—O1	1.4260 (14)	C5—C6	1.398 (2)
S1—N1	1.6405 (15)	C5—H5	0.9300
S1—C8	1.750 (2)	C6—C7	1.473 (2)
O3—C7	1.210 (2)	C7—C8	1.510 (3)
N1—C1	1.424 (2)	C8—H8A	0.9700
N1—C9	1.477 (2)	C8—H8B	0.9700
C1—C2	1.395 (2)	C9—C10	1.503 (3)
C1—C6	1.400 (2)	C9—H9A	0.9700
C2—C3	1.380 (3)	C9—H9B	0.9700
C2—H2	0.9300	C10—H10A	0.9600
C3—C4	1.368 (3)	C10—H10B	0.9600
C3—H3	0.9300	C10—H10C	0.9600
C4—C5	1.363 (3)
O2—S1—O1	118.03 (10)	C5—C6—C1	119.07 (16)
O2—S1—N1	107.40 (9)	C5—C6—C7	117.38 (17)
O1—S1—N1	111.71 (9)	C1—C6—C7	123.54 (16)
O2—S1—C8	110.60 (10)	O3—C7—C6	122.76 (18)
O1—S1—C8	107.58 (9)	O3—C7—C8	119.04 (17)
N1—S1—C8	100.05 (8)	C6—C7—C8	118.20 (16)
C1—N1—C9	121.18 (14)	C7—C8—S1	112.13 (13)
C1—N1—S1	117.15 (12)	C7—C8—H8A	109.2
C9—N1—S1	118.59 (12)	S1—C8—H8A	109.2
C2—C1—C6	119.03 (16)	C7—C8—H8B	109.2
C2—C1—N1	120.08 (16)	S1—C8—H8B	109.2
C6—C1—N1	120.87 (15)	H8A—C8—H8B	107.9
C3—C2—C1	119.70 (18)	N1—C9—C10	111.54 (17)
C3—C2—H2	120.2	N1—C9—H9A	109.3
C1—C2—H2	120.2	C10—C9—H9A	109.3
C4—C3—C2	121.64 (18)	N1—C9—H9B	109.3
C4—C3—H3	119.2	C10—C9—H9B	109.3
C2—C3—H3	119.2	H9A—C9—H9B	108.0
C5—C4—C3	119.13 (18)	C9—C10—H10A	109.5
C5—C4—H4	120.4	C9—C10—H10B	109.5
C3—C4—H4	120.4	H10A—C10—H10B	109.5
C4—C5—C6	121.41 (18)	C9—C10—H10C	109.5
C4—C5—H5	119.3	H10A—C10—H10C	109.5
C6—C5—H5	119.3	H10B—C10—H10C	109.5
O2—S1—N1—C1	−170.18 (14)	C4—C5—C6—C7	178.61 (17)
O1—S1—N1—C1	58.92 (16)	C2—C1—C6—C5	1.7 (3)
C8—S1—N1—C1	−54.70 (16)	N1—C1—C6—C5	−179.84 (16)
O2—S1—N1—C9	29.41 (18)	C2—C1—C6—C7	−178.16 (17)
O1—S1—N1—C9	−101.49 (15)	N1—C1—C6—C7	0.3 (3)
C8—S1—N1—C9	144.89 (15)	C5—C6—C7—O3	0.5 (3)
C9—N1—C1—C2	9.9 (3)	C1—C6—C7—O3	−179.56 (17)
S1—N1—C1—C2	−149.95 (15)	C5—C6—C7—C8	−178.23 (15)
C9—N1—C1—C6	−168.48 (17)	C1—C6—C7—C8	1.7 (3)
S1—N1—C1—C6	31.6 (2)	O3—C7—C8—S1	149.47 (16)
C6—C1—C2—C3	−0.7 (3)	C6—C7—C8—S1	−31.7 (2)
N1—C1—C2—C3	−179.18 (17)	O2—S1—C8—C7	166.56 (13)
C1—C2—C3—C4	−0.8 (3)	O1—S1—C8—C7	−63.23 (15)
C2—C3—C4—C5	1.2 (3)	N1—S1—C8—C7	53.53 (15)
C3—C4—C5—C6	−0.2 (3)	C1—N1—C9—C10	75.8 (2)
C4—C5—C6—C1	−1.3 (3)	S1—N1—C9—C10	−124.64 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3i	0.93	2.56	3.478 (3)	169
C8—H8A···O1ii	0.97	2.50	3.388 (3)	152
C9—H9B···O2	0.97	2.36	2.855 (3)	111

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	0.93	2.56	3.478 (3)	169
C8—H8A⋯O1ii	0.97	2.50	3.388 (3)	152
C9—H9B⋯O2	0.97	2.36	2.855 (3)	111

Symmetry codes: (i) ; (ii) .