N-acetonylsaccharin.

IN THE TITLE COMPOUND [SYSTEMATIC NAME: 2-(2-oxoprop-yl)-1,2-benzothia-zol-3(2H)-one 1,1-dioxide], C(10)H(9)NO(4)S, the benzo-thia-zole unit is essentially planar [maximum deviation = 0.0490 (9) Å for the S atom] and the oxopropyl group is inclined at an angle 75.61 (8)° with respect to its mean plane. In the crystal, mol-ecules are held together by weak inter-molecular C-H⋯O non-classical hydrogen bonds, resulting in centrosymmetric dimeric units, forming 14-membered ring systems which may be described as R(2) (2)(14) ring motifs. Moreover, mol-ecules lying about inversion centers show π-π inter-actions, with centroid-centroid separations between the benzene rings of 3.676 (2) Å.

Related literature

For the crystal structure of a benzothia­zine, see: Ahmad et al. (2008 ▶). For the biological activity of sacharine derivatives, see: Kapui et al. (2003 ▶); Singh et al. (2007 ▶); Vaccarino et al. (2007 ▶). For graph-set notation of ring motifs, see: Bernstein et al. (1994 ▶).

Experimental

Crystal data

C10H9NO4S

M = 239.24

Monoclinic,

a = 7.475 (3) Å

b = 8.975 (4) Å

c = 15.923 (7) Å

β = 101.028 (18)°

V = 1048.5 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 200 K

0.12 × 0.12 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.964, T max = 0.982

3984 measured reflections

2382 independent reflections

2106 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 1.04

2382 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.41 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); 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 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030773/si2191sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030773/si2191Isup2.hkl

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

C10H9NO4S	F(000) = 496
Mr = 239.24	Dx = 1.516 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3984 reflections
a = 7.475 (3) Å	θ = 3.4–27.5°
b = 8.975 (4) Å	µ = 0.31 mm−1
c = 15.923 (7) Å	T = 200 K
β = 101.028 (18)°	Block, colorless
V = 1048.5 (8) Å3	0.12 × 0.12 × 0.06 mm
Z = 4

Nonius KappaCCD diffractometer	2382 independent reflections
Radiation source: fine-focus sealed tube	2106 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −9→9
Tmin = 0.964, Tmax = 0.982	k = −8→11
3984 measured reflections	l = −20→20

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0444P)2 + 0.8524P] where P = (Fo2 + 2Fc2)/3
2382 reflections	(Δ/σ)max = 0.005
146 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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	0.26215 (6)	0.14487 (5)	0.47133 (3)	0.02833 (15)
O1	0.09274 (19)	0.22262 (17)	0.44859 (10)	0.0401 (4)
O2	0.2659 (2)	−0.00422 (16)	0.44012 (10)	0.0406 (4)
O3	0.5536 (2)	0.25086 (18)	0.68078 (9)	0.0397 (4)
O4	0.1159 (2)	0.30470 (18)	0.66321 (11)	0.0504 (4)
N1	0.3345 (2)	0.14693 (19)	0.57704 (10)	0.0319 (4)
C1	0.7056 (3)	0.3839 (2)	0.53131 (12)	0.0306 (4)
H1	0.7806	0.4139	0.5837	0.037*
C2	0.7458 (3)	0.4271 (2)	0.45301 (13)	0.0335 (4)
H2	0.8482	0.4894	0.4520	0.040*
C3	0.6389 (3)	0.3809 (2)	0.37630 (13)	0.0355 (4)
H3	0.6702	0.4113	0.3238	0.043*
C4	0.4873 (3)	0.2911 (2)	0.37500 (12)	0.0317 (4)
H4	0.4148	0.2579	0.3227	0.038*
C5	0.4466 (2)	0.2519 (2)	0.45337 (12)	0.0267 (4)
C6	0.5534 (2)	0.29595 (19)	0.53062 (11)	0.0263 (4)
C7	0.4875 (3)	0.2339 (2)	0.60579 (12)	0.0295 (4)
C8	0.2358 (3)	0.0693 (2)	0.63437 (13)	0.0350 (4)
H8A	0.3243	0.0170	0.6788	0.042*
H8B	0.1557	−0.0068	0.6014	0.042*
C9	0.1209 (3)	0.1729 (2)	0.67757 (13)	0.0346 (4)
C10	0.0182 (3)	0.1008 (3)	0.73859 (14)	0.0500 (6)
H10A	0.0730	0.0039	0.7564	0.060*
H10B	−0.1092	0.0867	0.7104	0.060*
H10C	0.0235	0.1646	0.7890	0.060*

	U11	U22	U33	U12	U13	U23
S1	0.0268 (2)	0.0309 (2)	0.0263 (2)	0.00255 (17)	0.00270 (17)	−0.00209 (17)
O1	0.0271 (7)	0.0465 (8)	0.0446 (9)	0.0070 (6)	0.0015 (6)	0.0000 (7)
O2	0.0477 (9)	0.0311 (7)	0.0415 (8)	−0.0004 (6)	0.0049 (7)	−0.0067 (6)
O3	0.0419 (8)	0.0536 (9)	0.0221 (7)	−0.0003 (7)	0.0024 (6)	0.0009 (6)
O4	0.0612 (11)	0.0388 (8)	0.0582 (11)	0.0046 (8)	0.0288 (9)	0.0006 (7)
N1	0.0303 (8)	0.0411 (9)	0.0252 (8)	−0.0019 (7)	0.0077 (6)	−0.0004 (6)
C1	0.0278 (9)	0.0337 (9)	0.0289 (9)	0.0050 (7)	0.0021 (7)	−0.0009 (7)
C2	0.0286 (9)	0.0344 (10)	0.0393 (11)	0.0029 (8)	0.0105 (8)	0.0018 (8)
C3	0.0367 (10)	0.0430 (11)	0.0291 (10)	0.0065 (8)	0.0124 (8)	0.0051 (8)
C4	0.0334 (9)	0.0382 (10)	0.0230 (9)	0.0071 (8)	0.0043 (7)	−0.0016 (7)
C5	0.0251 (8)	0.0287 (8)	0.0259 (9)	0.0051 (7)	0.0040 (7)	−0.0006 (7)
C6	0.0278 (9)	0.0280 (8)	0.0229 (8)	0.0061 (7)	0.0043 (7)	−0.0008 (7)
C7	0.0290 (9)	0.0345 (9)	0.0249 (9)	0.0052 (7)	0.0045 (7)	0.0005 (7)
C8	0.0389 (10)	0.0345 (10)	0.0330 (10)	−0.0006 (8)	0.0103 (8)	0.0053 (8)
C9	0.0322 (10)	0.0435 (11)	0.0288 (10)	−0.0055 (9)	0.0075 (8)	0.0006 (8)
C10	0.0500 (13)	0.0703 (16)	0.0330 (12)	−0.0204 (12)	0.0159 (10)	−0.0010 (11)

S1—O2	1.4295 (15)	C3—C4	1.388 (3)
S1—O1	1.4305 (15)	C3—H3	0.9500
S1—N1	1.6667 (18)	C4—C5	1.385 (3)
S1—C5	1.7485 (19)	C4—H4	0.9500
O3—C7	1.211 (2)	C5—C6	1.389 (3)
O4—C9	1.204 (3)	C6—C7	1.487 (3)
N1—C7	1.388 (3)	C8—C9	1.517 (3)
N1—C8	1.456 (2)	C8—H8A	0.9900
C1—C6	1.383 (3)	C8—H8B	0.9900
C1—C2	1.392 (3)	C9—C10	1.496 (3)
C1—H1	0.9500	C10—H10A	0.9800
C2—C3	1.389 (3)	C10—H10B	0.9800
C2—H2	0.9500	C10—H10C	0.9800
O2—S1—O1	116.35 (9)	C6—C5—S1	110.42 (14)
O2—S1—N1	109.71 (9)	C1—C6—C5	120.11 (17)
O1—S1—N1	110.53 (9)	C1—C6—C7	127.31 (17)
O2—S1—C5	112.90 (9)	C5—C6—C7	112.55 (16)
O1—S1—C5	112.22 (9)	O3—C7—N1	123.44 (18)
N1—S1—C5	92.60 (8)	O3—C7—C6	127.64 (18)
C7—N1—C8	123.13 (17)	N1—C7—C6	108.91 (16)
C7—N1—S1	115.29 (13)	N1—C8—C9	112.95 (16)
C8—N1—S1	121.49 (14)	N1—C8—H8A	109.0
C6—C1—C2	118.03 (18)	C9—C8—H8A	109.0
C6—C1—H1	121.0	N1—C8—H8B	109.0
C2—C1—H1	121.0	C9—C8—H8B	109.0
C3—C2—C1	121.19 (19)	H8A—C8—H8B	107.8
C3—C2—H2	119.4	O4—C9—C10	123.2 (2)
C1—C2—H2	119.4	O4—C9—C8	121.05 (18)
C4—C3—C2	121.16 (18)	C10—C9—C8	115.78 (19)
C4—C3—H3	119.4	C9—C10—H10A	109.5
C2—C3—H3	119.4	C9—C10—H10B	109.5
C5—C4—C3	116.97 (18)	H10A—C10—H10B	109.5
C5—C4—H4	121.5	C9—C10—H10C	109.5
C3—C4—H4	121.5	H10A—C10—H10C	109.5
C4—C5—C6	122.52 (18)	H10B—C10—H10C	109.5
C4—C5—S1	127.07 (15)
O2—S1—N1—C7	120.12 (15)	C2—C1—C6—C7	178.29 (17)
O1—S1—N1—C7	−110.26 (15)	C4—C5—C6—C1	0.9 (3)
C5—S1—N1—C7	4.66 (15)	S1—C5—C6—C1	−179.02 (13)
O2—S1—N1—C8	−63.36 (17)	C4—C5—C6—C7	−177.06 (16)
O1—S1—N1—C8	66.26 (17)	S1—C5—C6—C7	3.04 (19)
C5—S1—N1—C8	−178.83 (15)	C8—N1—C7—O3	1.2 (3)
C6—C1—C2—C3	−1.4 (3)	S1—N1—C7—O3	177.61 (15)
C1—C2—C3—C4	0.6 (3)	C8—N1—C7—C6	179.96 (16)
C2—C3—C4—C5	0.9 (3)	S1—N1—C7—C6	−3.59 (19)
C3—C4—C5—C6	−1.7 (3)	C1—C6—C7—O3	1.1 (3)
C3—C4—C5—S1	178.21 (14)	C5—C6—C7—O3	178.91 (18)
O2—S1—C5—C4	63.10 (19)	C1—C6—C7—N1	−177.59 (17)
O1—S1—C5—C4	−70.77 (19)	C5—C6—C7—N1	0.2 (2)
N1—S1—C5—C4	175.78 (17)	C7—N1—C8—C9	74.6 (2)
O2—S1—C5—C6	−117.01 (13)	S1—N1—C8—C9	−101.65 (19)
O1—S1—C5—C6	109.12 (14)	N1—C8—C9—O4	0.4 (3)
N1—S1—C5—C6	−4.32 (14)	N1—C8—C9—C10	−178.98 (18)
C2—C1—C6—C5	0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O2i	0.98	2.57	3.324 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O2i	0.98	2.57	3.324 (3)	134

Symmetry code: (i) .