2,3-Dihydro-1λ(6),2-benzothia-zine-1,1,4-trione.

In the title compound, C(8)H(7)NO(3)S, the benzene ring is oriented at a dihedral angle of 69.25 (7)° to the S and O atoms of the sulfonyl group. The heterocyclic ring approximates to an envelope, with the N atom in the flap position. In the crystal, mol-ecules are linked by N-H⋯O(c) (c = carbon-yl) hydrogen bonds, forming C(5) chains along [001]. Two R(2) (2)(10) loops arise from pairs of C-H⋯O hydrogen bonds and a weak aromatic π-π stacking inter-action [centroid-centorid separation = 3.8404 (11) Å] also occurs.

Related literature

For chemical background and related structures, see: Siddiqui et al. (2007 ▶, 2008 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C8H7NO3S

M = 197.21

Monoclinic,

a = 8.4950 (4) Å

b = 13.7560 (5) Å

c = 7.6677 (3) Å

β = 113.214 (1)°

V = 823.48 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 296 K

0.35 × 0.15 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.915, T max = 0.938

7644 measured reflections

2017 independent reflections

1692 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.04

2017 reflections

121 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013827/hb6713sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013827/hb6713Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013827/hb6713Isup3.cml

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

C8H7NO3S	F(000) = 408
Mr = 197.21	Dx = 1.591 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1692 reflections
a = 8.4950 (4) Å	θ = 2.6–28.3°
b = 13.7560 (5) Å	µ = 0.36 mm−1
c = 7.6677 (3) Å	T = 296 K
β = 113.214 (1)°	Needle, light yellow
V = 823.48 (6) Å3	0.35 × 0.15 × 0.12 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2017 independent reflections
Radiation source: fine-focus sealed tube	1692 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 7.50 pixels mm-1	θmax = 28.3°, θmin = 2.6°
ω scans	h = −11→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→18
Tmin = 0.915, Tmax = 0.938	l = −10→10
7644 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0455P)2 + 0.3408P] where P = (Fo2 + 2Fc2)/3
2017 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.28018 (5)	0.04479 (3)	0.18815 (6)	0.0352 (2)
O1	0.21934 (19)	−0.00868 (10)	0.3084 (2)	0.0539 (5)
O2	0.25497 (18)	0.00747 (10)	0.00536 (19)	0.0499 (5)
O3	0.55335 (18)	0.29145 (11)	0.1183 (2)	0.0532 (5)
N1	0.4843 (2)	0.06118 (11)	0.3034 (2)	0.0405 (5)
C1	0.1985 (2)	0.16427 (11)	0.1625 (2)	0.0297 (4)
C2	0.0353 (2)	0.18011 (14)	0.1537 (3)	0.0392 (5)
C3	−0.0234 (2)	0.27484 (15)	0.1446 (3)	0.0447 (6)
C4	0.0788 (2)	0.35176 (14)	0.1427 (3)	0.0430 (6)
C5	0.2406 (2)	0.33587 (13)	0.1476 (3)	0.0363 (5)
C6	0.30357 (19)	0.24184 (11)	0.1576 (2)	0.0285 (4)
C7	0.4782 (2)	0.22672 (12)	0.1609 (2)	0.0331 (5)
C8	0.5621 (2)	0.12808 (13)	0.2121 (3)	0.0429 (6)
H1	0.502 (3)	0.0766 (17)	0.410 (3)	0.0486*
H2	−0.03448	0.12804	0.15398	0.0471*
H3	−0.13293	0.28633	0.13970	0.0537*
H4	0.03854	0.41499	0.13799	0.0516*
H5	0.30824	0.38842	0.14422	0.0436*
H8A	0.56037	0.09765	0.09725	0.0514*
H8B	0.68115	0.13745	0.29619	0.0514*

	U11	U22	U33	U12	U13	U23
S1	0.0387 (3)	0.0236 (2)	0.0436 (3)	−0.0023 (2)	0.0165 (2)	−0.0012 (2)
O1	0.0633 (10)	0.0355 (7)	0.0697 (10)	−0.0056 (6)	0.0335 (8)	0.0110 (6)
O2	0.0576 (9)	0.0383 (7)	0.0513 (8)	−0.0023 (6)	0.0188 (7)	−0.0148 (6)
O3	0.0408 (8)	0.0479 (8)	0.0783 (10)	−0.0039 (6)	0.0314 (7)	0.0131 (7)
N1	0.0384 (8)	0.0292 (8)	0.0486 (8)	0.0044 (6)	0.0116 (7)	0.0025 (6)
C1	0.0308 (8)	0.0278 (8)	0.0307 (7)	0.0003 (6)	0.0123 (6)	−0.0008 (6)
C2	0.0305 (9)	0.0446 (10)	0.0442 (9)	−0.0037 (7)	0.0164 (7)	0.0001 (8)
C3	0.0320 (9)	0.0579 (12)	0.0475 (10)	0.0120 (8)	0.0192 (8)	0.0034 (9)
C4	0.0462 (11)	0.0384 (10)	0.0452 (10)	0.0154 (8)	0.0189 (8)	0.0017 (8)
C5	0.0425 (10)	0.0273 (8)	0.0409 (9)	0.0022 (7)	0.0184 (7)	0.0013 (7)
C6	0.0295 (8)	0.0273 (8)	0.0299 (7)	0.0012 (6)	0.0129 (6)	0.0006 (6)
C7	0.0309 (8)	0.0327 (9)	0.0372 (8)	−0.0018 (7)	0.0152 (7)	−0.0016 (7)
C8	0.0321 (9)	0.0371 (10)	0.0625 (12)	0.0031 (7)	0.0219 (8)	−0.0036 (8)

S1—O1	1.4262 (16)	C4—C5	1.378 (3)
S1—O2	1.4273 (14)	C5—C6	1.390 (2)
S1—N1	1.6219 (18)	C6—C7	1.488 (2)
S1—C1	1.7646 (16)	C7—C8	1.511 (2)
O3—C7	1.213 (2)	C2—H2	0.9300
N1—C8	1.462 (3)	C3—H3	0.9300
N1—H1	0.80 (2)	C4—H4	0.9300
C1—C2	1.379 (3)	C5—H5	0.9300
C1—C6	1.401 (2)	C8—H8A	0.9700
C2—C3	1.387 (3)	C8—H8B	0.9700
C3—C4	1.372 (3)
O1—S1—O2	119.80 (9)	C1—C6—C7	122.30 (14)
O1—S1—N1	107.55 (9)	O3—C7—C6	121.31 (16)
O1—S1—C1	109.00 (9)	O3—C7—C8	119.00 (17)
O2—S1—N1	107.42 (9)	C6—C7—C8	119.66 (15)
O2—S1—C1	108.99 (8)	N1—C8—C7	115.70 (16)
N1—S1—C1	102.72 (8)	C1—C2—H2	121.00
S1—N1—C8	114.49 (12)	C3—C2—H2	120.00
C8—N1—H1	112.6 (18)	C2—C3—H3	120.00
S1—N1—H1	108.9 (19)	C4—C3—H3	120.00
C2—C1—C6	121.15 (15)	C3—C4—H4	120.00
S1—C1—C6	119.06 (13)	C5—C4—H4	120.00
S1—C1—C2	119.76 (13)	C4—C5—H5	120.00
C1—C2—C3	119.05 (17)	C6—C5—H5	120.00
C2—C3—C4	120.56 (18)	N1—C8—H8A	108.00
C3—C4—C5	120.39 (18)	N1—C8—H8B	108.00
C4—C5—C6	120.48 (17)	C7—C8—H8A	108.00
C5—C6—C7	119.36 (15)	C7—C8—H8B	108.00
C1—C6—C5	118.34 (16)	H8A—C8—H8B	107.00
O1—S1—N1—C8	−170.75 (13)	C2—C1—C6—C7	−178.08 (15)
O2—S1—N1—C8	59.04 (14)	S1—C1—C6—C5	−176.60 (13)
C1—S1—N1—C8	−55.82 (14)	C1—C2—C3—C4	0.6 (3)
O1—S1—C1—C2	−36.22 (16)	C2—C3—C4—C5	0.8 (3)
O2—S1—C1—C2	96.19 (16)	C3—C4—C5—C6	−1.0 (3)
N1—S1—C1—C2	−150.09 (14)	C4—C5—C6—C1	0.0 (3)
O1—S1—C1—C6	141.74 (12)	C4—C5—C6—C7	179.44 (17)
O2—S1—C1—C6	−85.85 (14)	C1—C6—C7—C8	−13.2 (2)
N1—S1—C1—C6	27.87 (14)	C5—C6—C7—O3	−14.6 (2)
S1—N1—C8—C7	53.31 (19)	C1—C6—C7—O3	164.83 (15)
S1—C1—C2—C3	176.30 (15)	C5—C6—C7—C8	167.41 (16)
C6—C1—C2—C3	−1.6 (3)	O3—C7—C8—N1	166.31 (15)
S1—C1—C6—C7	3.99 (19)	C6—C7—C8—N1	−15.6 (2)
C2—C1—C6—C5	1.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.80 (2)	2.34 (2)	3.028 (2)	144 (2)
C2—H2···O2ii	0.93	2.58	3.443 (2)	154
C8—H8A···O2iii	0.97	2.48	3.273 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.80 (2)	2.34 (2)	3.028 (2)	144 (2)
C2—H2⋯O2ii	0.93	2.58	3.443 (2)	154
C8—H8A⋯O2iii	0.97	2.48	3.273 (2)	139

Symmetry codes: (i) ; (ii) ; (iii) .