Methyl 3-oxo-2,3-dihydro-1,2-benzothia-zole-2-acetate 1,1-dioxide.

The title mol-ecule, C(10)H(9)NO(5)S, is composed of two essentially planar units with a dihedral angle of 89.16 (6)° between them. In the crystal structure, there are weak inter-molecular C-H⋯O inter-actions resulting in dimeric pairs of mol-ecules about inversion centres and chains of mol-ecules extended along the a and c axes, thus stabilizing the structure. In addition, benzothia-zole rings lying parallel to each other with centroid-centroid distances of 3.679 (2) and 3.999 (2) Å indicate the existence of π-π stacking inter-actions.

Related literature

For related literature, see: Kapui et al. (2003 ▶); Masashi et al. (1999 ▶); Manjarrez et al. (1996 ▶); Siddiqui, Ahmad, Khan, Siddiqui & Parvez (2007 ▶); Siddiqui, Ahmad, Khan, Siddiqui & Weaver (2007 ▶); Siddiqui, Ahmad, Siddiqui et al. (2007 ▶); Siddiqui et al. (2008 ▶); Xu et al. (2005 ▶, 2006 ▶).

Experimental

Crystal data

C10H9NO5S

M = 255.24

Triclinic,

a = 7.765 (3) Å

b = 8.496 (3) Å

c = 8.776 (4) Å

α = 104.39 (2)°

β = 100.58 (2)°

γ = 94.30 (2)°

V = 546.8 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 173 (2) K

0.16 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.953, T max = 0.976

4654 measured reflections

2468 independent reflections

2040 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.111

S = 1.03

2468 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.43 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: SAPI91 (Fan, 1991 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009951/lh2607sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009951/lh2607Isup2.hkl

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

C10H9NO5S	Z = 2
Mr = 255.24	F000 = 264
Triclinic, P1	Dx = 1.550 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.765 (3) Å	Cell parameters from 4654 reflections
b = 8.496 (3) Å	θ = 3.9–27.4º
c = 8.776 (4) Å	µ = 0.31 mm−1
α = 104.39 (2)º	T = 173 (2) K
β = 100.58 (2)º	Block, colourless
γ = 94.30 (2)º	0.16 × 0.10 × 0.08 mm
V = 546.8 (4) Å3

Nonius KappaCCD diffractometer	2468 independent reflections
Radiation source: fine-focus sealed tube	2040 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
T = 173(2) K	θmax = 27.4º
ω and φ scans	θmin = 3.9º
Absorption correction: multi-scan(SORTAV; Blessing, 1997)	h = −10→9
Tmin = 0.953, Tmax = 0.976	k = −11→10
4654 measured reflections	l = −11→11

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.056P)2 + 0.29P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2468 reflections	Δρmax = 0.46 e Å−3
155 parameters	Δρmin = −0.43 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	0.25284 (6)	0.37128 (6)	1.06522 (6)	0.02602 (16)
O1	−0.07412 (18)	0.18372 (19)	0.67891 (17)	0.0354 (3)
O2	0.40672 (17)	0.29152 (17)	1.08988 (17)	0.0320 (3)
O3	0.2727 (2)	0.54422 (17)	1.13620 (18)	0.0372 (4)
O4	0.3882 (2)	0.14876 (17)	0.70088 (18)	0.0369 (4)
O5	0.41016 (18)	0.33528 (17)	0.56027 (16)	0.0312 (3)
N1	0.1635 (2)	0.3311 (2)	0.87005 (18)	0.0275 (4)
C1	0.0687 (2)	0.2676 (2)	1.1032 (2)	0.0243 (4)
C2	0.0451 (3)	0.2516 (2)	1.2517 (2)	0.0303 (4)
H2	0.1321	0.2987	1.3471	0.036*
C3	−0.1118 (3)	0.1633 (3)	1.2543 (3)	0.0325 (4)
H3	−0.1321	0.1482	1.3535	0.039*
C4	−0.2397 (3)	0.0968 (2)	1.1148 (3)	0.0329 (5)
H4	−0.3467	0.0384	1.1202	0.040*
C5	−0.2128 (3)	0.1147 (2)	0.9669 (2)	0.0297 (4)
H5	−0.3005	0.0698	0.8716	0.036*
C6	−0.0558 (2)	0.1990 (2)	0.9619 (2)	0.0245 (4)
C7	−0.0003 (2)	0.2326 (2)	0.8179 (2)	0.0263 (4)
C8	0.2499 (3)	0.3960 (2)	0.7616 (2)	0.0292 (4)
H8A	0.3291	0.4972	0.8238	0.035*
H8B	0.1593	0.4256	0.6819	0.035*
C9	0.3566 (2)	0.2757 (2)	0.6733 (2)	0.0268 (4)
C10	0.5248 (3)	0.2391 (3)	0.4726 (3)	0.0435 (6)
H10A	0.5553	0.2910	0.3914	0.052*
H10B	0.4638	0.1284	0.4195	0.052*
H10C	0.6329	0.2329	0.5475	0.052*

	U11	U22	U33	U12	U13	U23
S1	0.0241 (3)	0.0292 (3)	0.0245 (3)	0.00447 (18)	0.00385 (18)	0.00737 (18)
O1	0.0311 (7)	0.0495 (9)	0.0236 (7)	0.0080 (6)	0.0024 (6)	0.0076 (6)
O2	0.0225 (7)	0.0398 (8)	0.0339 (8)	0.0068 (6)	0.0027 (6)	0.0117 (6)
O3	0.0426 (9)	0.0266 (7)	0.0379 (8)	0.0026 (6)	0.0035 (7)	0.0045 (6)
O4	0.0472 (9)	0.0316 (8)	0.0378 (8)	0.0101 (7)	0.0158 (7)	0.0136 (6)
O5	0.0308 (7)	0.0441 (8)	0.0252 (7)	0.0126 (6)	0.0102 (6)	0.0158 (6)
N1	0.0242 (8)	0.0376 (9)	0.0217 (8)	0.0022 (7)	0.0048 (6)	0.0102 (7)
C1	0.0226 (9)	0.0270 (9)	0.0251 (9)	0.0069 (7)	0.0061 (7)	0.0083 (7)
C2	0.0307 (10)	0.0375 (11)	0.0241 (10)	0.0094 (8)	0.0053 (8)	0.0095 (8)
C3	0.0377 (11)	0.0375 (11)	0.0309 (11)	0.0155 (9)	0.0161 (9)	0.0151 (8)
C4	0.0269 (10)	0.0328 (10)	0.0452 (12)	0.0065 (8)	0.0137 (9)	0.0164 (9)
C5	0.0245 (9)	0.0314 (10)	0.0328 (10)	0.0046 (8)	0.0035 (8)	0.0095 (8)
C6	0.0252 (9)	0.0248 (9)	0.0240 (9)	0.0086 (7)	0.0042 (7)	0.0066 (7)
C7	0.0261 (9)	0.0288 (9)	0.0237 (10)	0.0051 (7)	0.0073 (7)	0.0042 (7)
C8	0.0305 (10)	0.0329 (10)	0.0297 (10)	0.0075 (8)	0.0115 (8)	0.0135 (8)
C9	0.0230 (9)	0.0325 (10)	0.0243 (9)	0.0000 (7)	0.0032 (7)	0.0090 (8)
C10	0.0436 (13)	0.0656 (15)	0.0302 (11)	0.0250 (11)	0.0173 (10)	0.0169 (10)

S1—O2	1.4258 (15)	C3—C4	1.389 (3)
S1—O3	1.4306 (15)	C3—H3	0.9500
S1—N1	1.6640 (18)	C4—C5	1.395 (3)
S1—C1	1.7504 (19)	C4—H4	0.9500
O1—C7	1.202 (2)	C5—C6	1.380 (3)
O4—C9	1.196 (2)	C5—H5	0.9500
O5—C9	1.335 (2)	C6—C7	1.492 (3)
O5—C10	1.449 (2)	C8—C9	1.517 (3)
N1—C7	1.402 (3)	C8—H8A	0.9900
N1—C8	1.449 (2)	C8—H8B	0.9900
C1—C2	1.387 (3)	C10—H10A	0.9800
C1—C6	1.388 (3)	C10—H10B	0.9800
C2—C3	1.389 (3)	C10—H10C	0.9800
C2—H2	0.9500
O2—S1—O3	116.71 (9)	C6—C5—H5	120.7
O2—S1—N1	110.73 (9)	C4—C5—H5	120.7
O3—S1—N1	109.35 (9)	C5—C6—C1	119.81 (18)
O2—S1—C1	112.26 (9)	C5—C6—C7	127.38 (17)
O3—S1—C1	112.83 (9)	C1—C6—C7	112.78 (17)
N1—S1—C1	92.26 (9)	O1—C7—N1	123.33 (18)
C9—O5—C10	115.33 (16)	O1—C7—C6	128.71 (18)
C7—N1—C8	122.31 (16)	N1—C7—C6	107.93 (16)
C7—N1—S1	116.00 (13)	N1—C8—C9	112.82 (16)
C8—N1—S1	121.68 (13)	N1—C8—H8A	109.0
C2—C1—C6	122.73 (18)	C9—C8—H8A	109.0
C2—C1—S1	126.37 (15)	N1—C8—H8B	109.0
C6—C1—S1	110.90 (14)	C9—C8—H8B	109.0
C1—C2—C3	116.80 (19)	H8A—C8—H8B	107.8
C1—C2—H2	121.6	O4—C9—O5	125.61 (18)
C3—C2—H2	121.6	O4—C9—C8	125.59 (18)
C2—C3—C4	121.34 (19)	O5—C9—C8	108.80 (16)
C2—C3—H3	119.3	O5—C10—H10A	109.5
C4—C3—H3	119.3	O5—C10—H10B	109.5
C3—C4—C5	120.73 (19)	H10A—C10—H10B	109.5
C3—C4—H4	119.6	O5—C10—H10C	109.5
C5—C4—H4	119.6	H10A—C10—H10C	109.5
C6—C5—C4	118.57 (18)	H10B—C10—H10C	109.5
O2—S1—N1—C7	111.37 (15)	C2—C1—C6—C5	1.8 (3)
O3—S1—N1—C7	−118.66 (15)	S1—C1—C6—C5	−178.65 (14)
C1—S1—N1—C7	−3.48 (15)	C2—C1—C6—C7	−179.84 (17)
O2—S1—N1—C8	−69.24 (17)	S1—C1—C6—C7	−0.3 (2)
O3—S1—N1—C8	60.73 (17)	C8—N1—C7—O1	6.2 (3)
C1—S1—N1—C8	175.91 (15)	S1—N1—C7—O1	−174.37 (15)
O2—S1—C1—C2	68.07 (19)	C8—N1—C7—C6	−175.64 (16)
O3—S1—C1—C2	−66.31 (19)	S1—N1—C7—C6	3.7 (2)
N1—S1—C1—C2	−178.43 (18)	C5—C6—C7—O1	−5.9 (3)
O2—S1—C1—C6	−111.44 (14)	C1—C6—C7—O1	175.94 (19)
O3—S1—C1—C6	114.19 (14)	C5—C6—C7—N1	176.14 (18)
N1—S1—C1—C6	2.07 (14)	C1—C6—C7—N1	−2.0 (2)
C6—C1—C2—C3	−0.4 (3)	C7—N1—C8—C9	−84.4 (2)
S1—C1—C2—C3	−179.86 (15)	S1—N1—C8—C9	96.29 (18)
C1—C2—C3—C4	−1.0 (3)	C10—O5—C9—O4	−3.8 (3)
C2—C3—C4—C5	1.0 (3)	C10—O5—C9—C8	175.82 (16)
C3—C4—C5—C6	0.4 (3)	N1—C8—C9—O4	−9.1 (3)
C4—C5—C6—C1	−1.8 (3)	N1—C8—C9—O5	171.21 (15)
C4—C5—C6—C7	−179.84 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5i	0.95	2.53	3.435 (3)	160
C4—H4···O4ii	0.95	2.54	3.209 (3)	128
C8—H8A···O2iii	0.99	2.49	3.435 (3)	159
C10—H10C···O1iv	0.98	2.47	3.431 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O5i	0.95	2.53	3.435 (3)	160
C4—H4⋯O4ii	0.95	2.54	3.209 (3)	128
C8—H8A⋯O2iii	0.99	2.49	3.435 (3)	159
C10—H10C⋯O1iv	0.98	2.47	3.431 (3)	167

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