Propan-2-yl 2-(1,1,3-trioxo-2,3-dihydro-1λ(6),2-benzothia-zol-2-yl)acetate.

In the title mol-ecule, C(12)H(13)NO(5)S, the benzisothia-zole ring system is essentially planar (r.m.s. deviation = 0.0169 Å) as is the -C-C(=O)-O-C- sequence of atoms in the vicinity of the acetate group (r.m.s. deviation = 0.0044 Å). The mean plane of these atoms forms a dihedral angle of 88.41 (7)° with the benzisothia-zole ring system. In the crystal, weak C-H⋯O hydrogen bonds involving methyl-ene and methyne H atoms form R(4) (3)(20) graph-set motifs.

Related literature

For uses of 1,2-benzothia­zol-3(2H)-one 1,1-dioxide, see: Kap-Sun & Nicholas (1998 ▶). For the synthesis of non-steroidal anti-inflammatory drugs (NSAIDs) and their biological evaluation, see: Ahmad et al. (2011 ▶); Zia-ur-Rehman et al. (2009 ▶). For related structures, see: Sattar et al. (2012 ▶); Maliha et al. (2007 ▶); Siddiqui et al. (2007 ▶). For graph-set motifs, see: (Bernstein et al., 1995 ▶).

Experimental

Crystal data

C12H13NO5S

M = 283.29

Monoclinic,

a = 8.0922 (3) Å

b = 9.2314 (4) Å

c = 17.7414 (8) Å

β = 100.075 (2)°

V = 1304.89 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 173 K

0.14 × 0.12 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.964, T max = 0.984

5518 measured reflections

2953 independent reflections

2339 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.119

S = 1.11

2953 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.41 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: 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 datablock(s) global, I. DOI: 10.1107/S1600536812036148/lh5516sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036148/lh5516Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036148/lh5516Isup3.cml

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

C12H13NO5S	F(000) = 592
Mr = 283.29	Dx = 1.442 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2817 reflections
a = 8.0922 (3) Å	θ = 1.0–27.5°
b = 9.2314 (4) Å	µ = 0.26 mm−1
c = 17.7414 (8) Å	T = 173 K
β = 100.075 (2)°	Prism, colorless
V = 1304.89 (9) Å3	0.14 × 0.12 × 0.06 mm
Z = 4

Nonius KappaCCD diffractometer	2953 independent reflections
Radiation source: fine-focus sealed tube	2339 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω and φ scans	θmax = 27.4°, θmin = 3.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −10→10
Tmin = 0.964, Tmax = 0.984	k = −11→11
5518 measured reflections	l = −22→22

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0186P)2 + 1.8823P] where P = (Fo2 + 2Fc2)/3
2953 reflections	(Δ/σ)max = 0.001
174 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.43 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	0.71458 (8)	0.28520 (7)	0.59318 (4)	0.02941 (18)
O1	0.6975 (3)	0.4281 (2)	0.62206 (12)	0.0414 (5)
O2	0.8538 (2)	0.2573 (2)	0.55647 (11)	0.0423 (5)
O3	0.5438 (2)	−0.0124 (2)	0.70065 (10)	0.0335 (4)
O4	0.9985 (3)	−0.0077 (2)	0.68519 (12)	0.0488 (6)
O5	1.0959 (2)	0.1079 (2)	0.79588 (10)	0.0311 (4)
N1	0.7092 (3)	0.1656 (2)	0.66356 (12)	0.0277 (5)
C1	0.5243 (3)	0.2216 (3)	0.54085 (13)	0.0250 (5)
C2	0.4415 (3)	0.2730 (3)	0.47085 (14)	0.0321 (6)
H2	0.4873	0.3475	0.4438	0.039*
C3	0.2872 (3)	0.2088 (3)	0.44250 (15)	0.0362 (7)
H3	0.2259	0.2407	0.3948	0.043*
C4	0.2206 (3)	0.1002 (3)	0.48162 (15)	0.0350 (6)
H4	0.1149	0.0594	0.4605	0.042*
C5	0.3061 (3)	0.0497 (3)	0.55150 (15)	0.0293 (6)
H5	0.2605	−0.0248	0.5786	0.035*
C6	0.4602 (3)	0.1119 (3)	0.58023 (13)	0.0234 (5)
C7	0.5697 (3)	0.0762 (3)	0.65414 (14)	0.0257 (5)
C8	0.8296 (3)	0.1713 (3)	0.73484 (14)	0.0314 (6)
H8A	0.7737	0.1390	0.7773	0.038*
H8B	0.8656	0.2730	0.7451	0.038*
C9	0.9831 (3)	0.0785 (3)	0.73385 (14)	0.0301 (6)
C10	1.2566 (3)	0.0297 (3)	0.80553 (16)	0.0350 (6)
H10	1.2916	0.0173	0.7546	0.042*
C11	1.3818 (4)	0.1243 (4)	0.8560 (2)	0.0526 (9)
H11A	1.4929	0.0790	0.8629	0.063*
H11B	1.3475	0.1359	0.9060	0.063*
H11C	1.3864	0.2195	0.8320	0.063*
C12	1.2351 (4)	−0.1147 (4)	0.8396 (2)	0.0501 (8)
H12A	1.3404	−0.1691	0.8444	0.060*
H12B	1.1458	−0.1680	0.8065	0.060*
H12C	1.2048	−0.1022	0.8903	0.060*

	U11	U22	U33	U12	U13	U23
S1	0.0286 (3)	0.0264 (3)	0.0310 (3)	−0.0029 (3)	−0.0007 (2)	0.0048 (3)
O1	0.0497 (12)	0.0242 (10)	0.0452 (12)	−0.0044 (9)	−0.0059 (9)	0.0021 (9)
O2	0.0295 (10)	0.0523 (13)	0.0462 (12)	−0.0056 (10)	0.0100 (9)	0.0067 (10)
O3	0.0376 (10)	0.0338 (10)	0.0291 (9)	0.0005 (9)	0.0057 (8)	0.0080 (8)
O4	0.0480 (13)	0.0531 (14)	0.0386 (11)	0.0179 (11)	−0.0107 (9)	−0.0165 (10)
O5	0.0254 (9)	0.0375 (11)	0.0275 (9)	0.0022 (8)	−0.0034 (7)	−0.0044 (8)
N1	0.0281 (11)	0.0263 (11)	0.0257 (11)	−0.0001 (9)	−0.0035 (9)	0.0036 (9)
C1	0.0239 (12)	0.0249 (12)	0.0253 (12)	0.0039 (10)	0.0019 (9)	−0.0003 (10)
C2	0.0324 (14)	0.0362 (15)	0.0280 (13)	0.0062 (12)	0.0057 (11)	0.0066 (12)
C3	0.0323 (14)	0.0452 (17)	0.0281 (13)	0.0119 (13)	−0.0035 (11)	0.0039 (13)
C4	0.0257 (13)	0.0436 (16)	0.0329 (14)	0.0012 (12)	−0.0027 (11)	−0.0058 (13)
C5	0.0258 (13)	0.0315 (14)	0.0309 (13)	0.0000 (11)	0.0063 (10)	−0.0037 (11)
C6	0.0241 (12)	0.0225 (12)	0.0235 (12)	0.0030 (10)	0.0039 (9)	0.0009 (10)
C7	0.0258 (12)	0.0255 (13)	0.0254 (12)	0.0030 (10)	0.0036 (10)	0.0005 (10)
C8	0.0332 (14)	0.0313 (14)	0.0259 (12)	0.0005 (11)	−0.0057 (11)	−0.0020 (11)
C9	0.0323 (14)	0.0310 (14)	0.0239 (12)	0.0017 (11)	−0.0033 (10)	−0.0005 (11)
C10	0.0240 (13)	0.0438 (16)	0.0369 (14)	0.0018 (12)	0.0047 (11)	−0.0011 (13)
C11	0.0359 (17)	0.055 (2)	0.061 (2)	−0.0069 (15)	−0.0066 (15)	0.0023 (17)
C12	0.0375 (17)	0.0480 (19)	0.062 (2)	0.0002 (15)	0.0017 (15)	0.0066 (17)

S1—O2	1.420 (2)	C4—H4	0.9500
S1—O1	1.431 (2)	C5—C6	1.387 (3)
S1—N1	1.673 (2)	C5—H5	0.9500
S1—C1	1.754 (2)	C6—C7	1.485 (3)
O3—C7	1.206 (3)	C8—C9	1.511 (4)
O4—C9	1.197 (3)	C8—H8A	0.9900
O5—C9	1.329 (3)	C8—H8B	0.9900
O5—C10	1.471 (3)	C10—C12	1.486 (4)
N1—C7	1.385 (3)	C10—C11	1.508 (4)
N1—C8	1.456 (3)	C10—H10	1.0000
C1—C6	1.381 (3)	C11—H11A	0.9800
C1—C2	1.388 (3)	C11—H11B	0.9800
C2—C3	1.395 (4)	C11—H11C	0.9800
C2—H2	0.9500	C12—H12A	0.9800
C3—C4	1.381 (4)	C12—H12B	0.9800
C3—H3	0.9500	C12—H12C	0.9800
C4—C5	1.390 (4)
O2—S1—O1	117.72 (13)	O3—C7—C6	127.4 (2)
O2—S1—N1	110.45 (12)	N1—C7—C6	108.8 (2)
O1—S1—N1	108.93 (12)	N1—C8—C9	113.3 (2)
O2—S1—C1	112.96 (12)	N1—C8—H8A	108.9
O1—S1—C1	111.56 (12)	C9—C8—H8A	108.9
N1—S1—C1	92.23 (11)	N1—C8—H8B	108.9
C9—O5—C10	117.5 (2)	C9—C8—H8B	108.9
C7—N1—C8	122.3 (2)	H8A—C8—H8B	107.7
C7—N1—S1	115.50 (16)	O4—C9—O5	126.2 (2)
C8—N1—S1	121.56 (18)	O4—C9—C8	125.1 (2)
C6—C1—C2	122.6 (2)	O5—C9—C8	108.7 (2)
C6—C1—S1	110.48 (17)	O5—C10—C12	108.9 (2)
C2—C1—S1	126.9 (2)	O5—C10—C11	105.9 (2)
C1—C2—C3	116.0 (3)	C12—C10—C11	113.1 (3)
C1—C2—H2	122.0	O5—C10—H10	109.6
C3—C2—H2	122.0	C12—C10—H10	109.6
C4—C3—C2	122.1 (2)	C11—C10—H10	109.6
C4—C3—H3	119.0	C10—C11—H11A	109.5
C2—C3—H3	119.0	C10—C11—H11B	109.5
C3—C4—C5	121.0 (2)	H11A—C11—H11B	109.5
C3—C4—H4	119.5	C10—C11—H11C	109.5
C5—C4—H4	119.5	H11A—C11—H11C	109.5
C6—C5—C4	117.7 (3)	H11B—C11—H11C	109.5
C6—C5—H5	121.2	C10—C12—H12A	109.5
C4—C5—H5	121.2	C10—C12—H12B	109.5
C1—C6—C5	120.7 (2)	H12A—C12—H12B	109.5
C1—C6—C7	113.0 (2)	C10—C12—H12C	109.5
C5—C6—C7	126.3 (2)	H12A—C12—H12C	109.5
O3—C7—N1	123.9 (2)	H12B—C12—H12C	109.5
O2—S1—N1—C7	−116.8 (2)	S1—C1—C6—C7	−1.2 (3)
O1—S1—N1—C7	112.4 (2)	C4—C5—C6—C1	0.9 (4)
C1—S1—N1—C7	−1.3 (2)	C4—C5—C6—C7	178.7 (2)
O2—S1—N1—C8	72.3 (2)	C8—N1—C7—O3	−6.7 (4)
O1—S1—N1—C8	−58.4 (2)	S1—N1—C7—O3	−177.5 (2)
C1—S1—N1—C8	−172.1 (2)	C8—N1—C7—C6	171.6 (2)
O2—S1—C1—C6	114.72 (19)	S1—N1—C7—C6	0.8 (3)
O1—S1—C1—C6	−110.00 (19)	C1—C6—C7—O3	178.5 (3)
N1—S1—C1—C6	1.38 (19)	C5—C6—C7—O3	0.6 (4)
O2—S1—C1—C2	−67.2 (3)	C1—C6—C7—N1	0.3 (3)
O1—S1—C1—C2	68.1 (3)	C5—C6—C7—N1	−177.6 (2)
N1—S1—C1—C2	179.5 (2)	C7—N1—C8—C9	97.6 (3)
C6—C1—C2—C3	0.9 (4)	S1—N1—C8—C9	−92.1 (3)
S1—C1—C2—C3	−177.0 (2)	C10—O5—C9—O4	1.2 (4)
C1—C2—C3—C4	−0.1 (4)	C10—O5—C9—C8	−179.3 (2)
C2—C3—C4—C5	−0.2 (4)	N1—C8—C9—O4	−10.1 (4)
C3—C4—C5—C6	−0.2 (4)	N1—C8—C9—O5	170.5 (2)
C2—C1—C6—C5	−1.3 (4)	C9—O5—C10—C12	−82.6 (3)
S1—C1—C6—C5	176.86 (19)	C9—O5—C10—C11	155.5 (2)
C2—C1—C6—C7	−179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O3i	0.99	2.27	3.236 (3)	166
C10—H10···O3ii	1.00	2.42	3.245 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O3i	0.99	2.27	3.236 (3)	166
C10—H10⋯O3ii	1.00	2.42	3.245 (3)	140

Symmetry codes: (i) ; (ii) .