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

In the crystal structure of the title compound, C(9)H(9)NO(3)S, there is distorted tetra-hedral geometry around the S atom. The sulfonyl group is almost normal to the benzene ring, while the carbonyl O atom and methyl C atom are on opposite sides of this ring. The heterocyclic ring adopts a half-boat conformation with the S atom out of the plane. The mol-ecules are dimerized by hydrogen bonding involving the benzene ring and the sulfonyl group. These dimers are linked to each other in the same way. There is an intra-molecular hydrogen bond between a methyl C-H group and a sulfonyl O atom, and a π-π inter-action between the aromatic rings of two dimers at a centroid-to-centroid distance of 3.6373 (13) Å.

Related literature

For related literature, see: Cremer & Pople (1975 ▶); Harmata et al. (2004 ▶); Lombardino (1972 ▶); Misu & Togo (2003 ▶); Shafiq et al. (2008 ▶); Siddiqui et al. (2007 ▶).

Experimental

Crystal data

C9H9NO3S

M = 211.23

Triclinic,

a = 7.4553 (4) Å

b = 8.5437 (4) Å

c = 8.7097 (4) Å

α = 67.691 (2)°

β = 70.467 (2)°

γ = 66.327 (2)°

V = 459.09 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 296 (2) K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.952, T max = 0.971

7205 measured reflections

1787 independent reflections

1678 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.095

S = 1.09

1678 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.42 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/S1600536808003498/bq2063sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003498/bq2063Isup2.hkl

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

C9H9NO3S	Z = 2
Mr = 211.23	F000 = 220
Triclinic, P1	Dx = 1.528 Mg m−3
Hall symbol: -P 1	Mo Kα radiation radiation λ = 0.71073 Å
a = 7.4553 (4) Å	Cell parameters from 1678 reflections
b = 8.5437 (4) Å	θ = 2.6–25.9º
c = 8.7097 (4) Å	µ = 0.33 mm−1
α = 67.691 (2)º	T = 296 (2) K
β = 70.467 (2)º	Prismatic, colourless
γ = 66.327 (2)º	0.20 × 0.15 × 0.10 mm
V = 459.09 (4) Å3

Bruker Kappa-APEXII CCD diffractometer	1787 independent reflections
Radiation source: fine-focus sealed tube	1678 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
Detector resolution: 7.50 pixels mm-1	θmax = 25.9º
T = 296(2) K	θmin = 2.6º
ω scans	h = −9→9
Absorption correction: multi-scan(SADABS; Bruker, 2007)	k = −10→10
Tmin = 0.952, Tmax = 0.971	l = −10→10
7205 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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0531P)2 + 0.1411P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
1678 reflections	Δρmax = 0.22 e Å−3
127 parameters	Δρmin = −0.42 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	0.18773 (6)	0.94371 (5)	0.15987 (5)	0.03811 (16)
O1	−0.02000 (18)	0.95817 (16)	0.20416 (15)	0.0472 (3)
O2	0.2454 (2)	1.09673 (18)	0.05037 (17)	0.0618 (4)
O3	0.3153 (2)	0.46358 (19)	0.16958 (19)	0.0641 (4)
N1	0.2759 (2)	0.87608 (18)	0.33158 (17)	0.0410 (3)
C1	0.2522 (2)	0.71412 (19)	0.45108 (18)	0.0327 (3)
C2	0.2208 (3)	0.6907 (2)	0.6241 (2)	0.0447 (4)
H2	0.2151	0.7814	0.6616	0.054*
C3	0.1982 (3)	0.5318 (3)	0.7405 (2)	0.0540 (5)
H3	0.1782	0.5166	0.8559	0.065*
C4	0.2048 (3)	0.3964 (3)	0.6881 (2)	0.0548 (5)
H4	0.1883	0.2908	0.7672	0.066*
C5	0.2359 (2)	0.4185 (2)	0.5186 (2)	0.0462 (4)
H5	0.2398	0.3270	0.4833	0.055*
C6	0.2618 (2)	0.57543 (19)	0.39688 (19)	0.0341 (3)
C7	0.2997 (2)	0.5863 (2)	0.2155 (2)	0.0399 (4)
C8	0.3241 (3)	0.7571 (2)	0.0823 (2)	0.0434 (4)
H8A	0.2785	0.7728	−0.0162	0.052*
H8B	0.4650	0.7481	0.0465	0.052*
C9	0.3194 (3)	1.0018 (3)	0.3773 (3)	0.0555 (5)
H9A	0.3301	1.1026	0.2801	0.083*
H9B	0.4436	0.9450	0.4149	0.083*
H9C	0.2133	1.0409	0.4671	0.083*

	U11	U22	U33	U12	U13	U23
S1	0.0511 (3)	0.0305 (2)	0.0313 (2)	−0.01201 (17)	−0.01384 (17)	−0.00395 (16)
O1	0.0486 (7)	0.0447 (7)	0.0460 (7)	−0.0040 (5)	−0.0179 (5)	−0.0152 (5)
O2	0.0921 (11)	0.0419 (7)	0.0480 (7)	−0.0301 (7)	−0.0247 (7)	0.0087 (6)
O3	0.0813 (10)	0.0563 (8)	0.0664 (9)	−0.0287 (7)	0.0007 (7)	−0.0364 (7)
N1	0.0614 (9)	0.0327 (7)	0.0371 (7)	−0.0211 (6)	−0.0205 (6)	−0.0033 (6)
C1	0.0317 (7)	0.0311 (7)	0.0322 (7)	−0.0082 (6)	−0.0092 (6)	−0.0055 (6)
C2	0.0462 (9)	0.0493 (10)	0.0356 (8)	−0.0100 (7)	−0.0121 (7)	−0.0113 (7)
C3	0.0454 (10)	0.0683 (13)	0.0313 (8)	−0.0154 (9)	−0.0091 (7)	0.0017 (8)
C4	0.0474 (10)	0.0477 (10)	0.0511 (11)	−0.0196 (8)	−0.0126 (8)	0.0116 (8)
C5	0.0414 (9)	0.0330 (8)	0.0580 (11)	−0.0132 (7)	−0.0129 (8)	−0.0029 (7)
C6	0.0304 (7)	0.0293 (7)	0.0386 (8)	−0.0084 (6)	−0.0068 (6)	−0.0072 (6)
C7	0.0364 (8)	0.0391 (8)	0.0458 (9)	−0.0101 (6)	−0.0046 (6)	−0.0193 (7)
C8	0.0500 (9)	0.0451 (9)	0.0317 (8)	−0.0113 (7)	−0.0055 (7)	−0.0141 (7)
C9	0.0770 (13)	0.0443 (10)	0.0624 (11)	−0.0274 (9)	−0.0267 (10)	−0.0143 (8)

S1—O2	1.4262 (13)	C3—H3	0.9300
S1—O1	1.4302 (13)	C4—C5	1.365 (3)
S1—N1	1.6429 (13)	C4—H4	0.9300
S1—C8	1.7574 (17)	C5—C6	1.397 (2)
O3—C7	1.209 (2)	C5—H5	0.9300
N1—C1	1.4175 (18)	C6—C7	1.482 (2)
N1—C9	1.452 (2)	C7—C8	1.515 (2)
C1—C2	1.393 (2)	C8—H8A	0.9700
C1—C6	1.402 (2)	C8—H8B	0.9700
C2—C3	1.387 (2)	C9—H9A	0.9600
C2—H2	0.9300	C9—H9B	0.9600
C3—C4	1.375 (3)	C9—H9C	0.9600
O2—S1—O1	118.32 (8)	C4—C5—C6	121.56 (17)
O2—S1—N1	107.31 (8)	C4—C5—H5	119.2
O1—S1—N1	110.55 (7)	C6—C5—H5	119.2
O2—S1—C8	111.61 (9)	C5—C6—C1	118.92 (15)
O1—S1—C8	107.95 (8)	C5—C6—C7	117.93 (14)
N1—S1—C8	99.47 (8)	C1—C6—C7	123.14 (14)
C1—N1—C9	121.70 (14)	O3—C7—C6	122.71 (16)
C1—N1—S1	116.58 (10)	O3—C7—C8	118.80 (15)
C9—N1—S1	119.32 (12)	C6—C7—C8	118.48 (13)
C2—C1—C6	119.27 (14)	C7—C8—S1	111.72 (11)
C2—C1—N1	120.09 (14)	C7—C8—H8A	109.3
C6—C1—N1	120.63 (13)	S1—C8—H8A	109.3
C3—C2—C1	119.87 (17)	C7—C8—H8B	109.3
C3—C2—H2	120.1	S1—C8—H8B	109.3
C1—C2—H2	120.1	H8A—C8—H8B	107.9
C4—C3—C2	121.05 (17)	N1—C9—H9A	109.5
C4—C3—H3	119.5	N1—C9—H9B	109.5
C2—C3—H3	119.5	H9A—C9—H9B	109.5
C5—C4—C3	119.31 (16)	N1—C9—H9C	109.5
C5—C4—H4	120.3	H9A—C9—H9C	109.5
C3—C4—H4	120.3	H9B—C9—H9C	109.5
O2—S1—N1—C1	−174.04 (12)	C4—C5—C6—C1	−1.1 (2)
O1—S1—N1—C1	55.60 (13)	C4—C5—C6—C7	178.55 (15)
C8—S1—N1—C1	−57.74 (13)	C2—C1—C6—C5	1.2 (2)
O2—S1—N1—C9	23.23 (18)	N1—C1—C6—C5	−179.41 (14)
O1—S1—N1—C9	−107.13 (15)	C2—C1—C6—C7	−178.43 (14)
C8—S1—N1—C9	139.53 (15)	N1—C1—C6—C7	0.9 (2)
C9—N1—C1—C2	15.9 (2)	C5—C6—C7—O3	−2.5 (2)
S1—N1—C1—C2	−146.39 (13)	C1—C6—C7—O3	177.15 (16)
C9—N1—C1—C6	−163.48 (16)	C5—C6—C7—C8	178.83 (14)
S1—N1—C1—C6	34.24 (18)	C1—C6—C7—C8	−1.5 (2)
C6—C1—C2—C3	−0.5 (2)	O3—C7—C8—S1	151.98 (15)
N1—C1—C2—C3	−179.84 (14)	C6—C7—C8—S1	−29.30 (18)
C1—C2—C3—C4	−0.4 (3)	O2—S1—C8—C7	166.75 (12)
C2—C3—C4—C5	0.6 (3)	O1—S1—C8—C7	−61.58 (13)
C3—C4—C5—C6	0.2 (3)	N1—S1—C8—C7	53.77 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.58	3.432 (2)	152
C4—H4···O2ii	0.93	2.46	3.238 (3)	142
C9—H9A···O2	0.96	2.31	2.830 (3)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.58	3.432 (2)	152
C4—H4⋯O2ii	0.93	2.46	3.238 (3)	142
C9—H9A⋯O2	0.96	2.31	2.830 (3)	113

Symmetry codes: (i) ; (ii) .