2-(2-Oxo-2-phenyl-ethyl)-1,2-benziso-thia-zol-3(2H)-one 1,1-dioxide.

In the title compound, C(15)H(11)NO(4)S, the benzothia-zole unit is essentially planar [maximum deviation = 0.0644 (14) Å for the N atom] and forms a dihedral angle 54.43 (6)° with the phenyl ring. In the crystal structure, weak bifurcated C-H⋯O hydrogen bonds involving the carbonyl O atoms as acceptors result in R(2) (2)(7) ring motifs.

Related literature

For the use of 1,2-benzisothia­zoline-3-one 1,1-dioxide (saccharine) as an inter­mediate in the preparation of medicinally important mol­ecules, see: Siddiqui et al. (2006 ▶); Zia-ur-Rehman et al. (2005 ▶, 2009 ▶). For the biological activity of saccharine, see: Singh et al. (2007 ▶); Vaccarino et al. (2007 ▶); Kapui et al. (2003 ▶). For related structures, see: Ahmad et al. (2008 ▶, 2009 ▶). For hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H11NO4S

M = 301.31

Monoclinic,

a = 8.0730 (2) Å

b = 9.1270 (3) Å

c = 18.0143 (6) Å

β = 95.4616 (18)°

V = 1321.31 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 173 K

0.18 × 0.14 × 0.10 mm

Data collection

Nonius diffractometer with Bruker APEXII CCD

Absorption correction: multi-scan (SORTAV;Blessing, 1997 ▶) T min = 0.955, T max = 0.974

15562 measured reflections

3016 independent reflections

2554 reflections with (I) > 2.0 σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.115

S = 1.09

3016 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.43 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: HKL 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/S1600536810005404/lh2990sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005404/lh2990Isup2.hkl

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

C15H11NO4S	F(000) = 624
Mr = 301.31	Dx = 1.515 Mg m−3
Monoclinic, P21/n	Melting point: 458 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.0730 (2) Å	Cell parameters from 3115 reflections
b = 9.1270 (3) Å	θ = 1.0–27.5°
c = 18.0143 (6) Å	µ = 0.26 mm−1
β = 95.4616 (18)°	T = 173 K
V = 1321.31 (7) Å3	Block, white
Z = 4	0.18 × 0.14 × 0.10 mm

Nonius APEX2 CCD diffractometer	3016 independent reflections
Radiation source: fine-focus sealed tube	2554 reflections with (I) > 2.0 σ(I)
graphite	Rint = 0.030
φ & ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SORTAV;Blessing, 1997)	h = −10→10
Tmin = 0.955, Tmax = 0.974	k = −11→11
15562 measured reflections	l = −23→23

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0412P)2 + 1.31P] where P = (Fo2 + 2Fc2)/3
3016 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.21297 (6)	0.21225 (5)	0.09588 (3)	0.02212 (14)
O1	0.0329 (2)	0.51326 (18)	0.20418 (9)	0.0369 (4)
O2	0.20831 (19)	0.06413 (16)	0.12149 (9)	0.0303 (4)
O3	0.35091 (18)	0.25411 (18)	0.05634 (8)	0.0306 (4)
O4	0.4233 (2)	0.5471 (2)	0.17286 (10)	0.0480 (5)
N1	0.1956 (2)	0.3264 (2)	0.16706 (9)	0.0256 (4)
C1	0.0221 (2)	0.2691 (2)	0.05015 (11)	0.0220 (4)
C2	−0.0584 (3)	0.2109 (2)	−0.01446 (11)	0.0258 (4)
H2	−0.0133	0.1309	−0.0396	0.031*
C3	−0.2090 (3)	0.2757 (3)	−0.04073 (12)	0.0301 (5)
H3	−0.2680	0.2395	−0.0851	0.036*
C4	−0.2743 (3)	0.3918 (3)	−0.00347 (12)	0.0306 (5)
H4	−0.3765	0.4347	−0.0231	0.037*
C5	−0.1931 (3)	0.4467 (2)	0.06218 (12)	0.0292 (5)
H5	−0.2394	0.5250	0.0882	0.035*
C6	−0.0424 (2)	0.3840 (2)	0.08864 (11)	0.0239 (4)
C7	0.0608 (3)	0.4209 (2)	0.15913 (11)	0.0251 (4)
C8	0.3232 (3)	0.3329 (2)	0.22988 (11)	0.0264 (4)
H8A	0.3841	0.2387	0.2336	0.032*
H8B	0.2690	0.3462	0.2765	0.032*
C9	0.4470 (3)	0.4575 (2)	0.22252 (11)	0.0274 (4)
C10	0.5913 (2)	0.4682 (2)	0.28032 (11)	0.0242 (4)
C11	0.6695 (3)	0.6038 (2)	0.29126 (13)	0.0294 (5)
H11	0.6312	0.6856	0.2619	0.035*
C12	0.8030 (3)	0.6194 (3)	0.34485 (13)	0.0333 (5)
H12	0.8551	0.7122	0.3526	0.040*
C13	0.8607 (3)	0.5001 (3)	0.38712 (12)	0.0347 (5)
H13	0.9522	0.5114	0.4239	0.042*
C14	0.7858 (3)	0.3650 (3)	0.37606 (13)	0.0354 (5)
H14	0.8271	0.2828	0.4045	0.042*
C15	0.6494 (3)	0.3493 (3)	0.32304 (12)	0.0291 (5)
H15	0.5961	0.2569	0.3162	0.035*

	U11	U22	U33	U12	U13	U23
S1	0.0205 (2)	0.0219 (3)	0.0228 (2)	0.00177 (18)	−0.00385 (18)	−0.00180 (19)
O1	0.0420 (9)	0.0322 (9)	0.0349 (9)	0.0078 (7)	−0.0040 (7)	−0.0128 (7)
O2	0.0332 (8)	0.0218 (8)	0.0347 (8)	0.0030 (6)	−0.0036 (6)	0.0007 (6)
O3	0.0222 (7)	0.0374 (9)	0.0320 (8)	0.0010 (6)	0.0007 (6)	0.0023 (7)
O4	0.0550 (11)	0.0412 (10)	0.0430 (10)	−0.0156 (9)	−0.0195 (8)	0.0180 (8)
N1	0.0260 (9)	0.0255 (9)	0.0235 (8)	0.0023 (7)	−0.0075 (7)	−0.0049 (7)
C1	0.0206 (9)	0.0222 (10)	0.0227 (9)	−0.0007 (8)	−0.0009 (7)	0.0020 (8)
C2	0.0265 (10)	0.0274 (11)	0.0228 (10)	−0.0021 (8)	−0.0019 (8)	−0.0020 (8)
C3	0.0295 (11)	0.0353 (12)	0.0236 (10)	−0.0031 (9)	−0.0075 (8)	0.0018 (9)
C4	0.0248 (10)	0.0322 (12)	0.0333 (11)	0.0029 (9)	−0.0054 (9)	0.0044 (9)
C5	0.0282 (10)	0.0253 (11)	0.0335 (11)	0.0052 (9)	−0.0006 (9)	0.0008 (9)
C6	0.0247 (10)	0.0202 (10)	0.0261 (10)	−0.0009 (8)	−0.0011 (8)	0.0012 (8)
C7	0.0263 (10)	0.0216 (10)	0.0266 (10)	−0.0013 (8)	−0.0020 (8)	−0.0004 (8)
C8	0.0281 (10)	0.0274 (11)	0.0219 (10)	−0.0009 (8)	−0.0071 (8)	0.0000 (8)
C9	0.0295 (10)	0.0271 (11)	0.0242 (10)	−0.0015 (9)	−0.0039 (8)	0.0003 (8)
C10	0.0232 (9)	0.0282 (11)	0.0209 (9)	−0.0019 (8)	0.0002 (7)	−0.0039 (8)
C11	0.0261 (10)	0.0275 (11)	0.0344 (12)	−0.0016 (9)	0.0016 (9)	−0.0025 (9)
C12	0.0274 (11)	0.0335 (12)	0.0390 (13)	−0.0090 (9)	0.0031 (9)	−0.0088 (10)
C13	0.0260 (11)	0.0488 (15)	0.0282 (11)	−0.0086 (10)	−0.0031 (9)	−0.0044 (10)
C14	0.0320 (12)	0.0400 (13)	0.0321 (12)	−0.0056 (10)	−0.0079 (9)	0.0073 (10)
C15	0.0303 (11)	0.0304 (11)	0.0251 (10)	−0.0070 (9)	−0.0050 (8)	0.0013 (9)

S1—O3	1.4298 (15)	C5—H5	0.9500
S1—O2	1.4301 (15)	C6—C7	1.489 (3)
S1—N1	1.6685 (18)	C8—C9	1.528 (3)
S1—C1	1.755 (2)	C8—H8A	0.9900
O1—C7	1.206 (3)	C8—H8B	0.9900
O4—C9	1.213 (3)	C9—C10	1.490 (3)
N1—C7	1.385 (3)	C10—C15	1.386 (3)
N1—C8	1.457 (2)	C10—C11	1.395 (3)
C1—C2	1.384 (3)	C11—C12	1.384 (3)
C1—C6	1.386 (3)	C11—H11	0.9500
C2—C3	1.394 (3)	C12—C13	1.383 (3)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.386 (3)	C13—C14	1.380 (3)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.390 (3)	C14—C15	1.395 (3)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.387 (3)	C15—H15	0.9500
O3—S1—O2	117.32 (10)	N1—C7—C6	108.51 (17)
O3—S1—N1	110.03 (9)	N1—C8—C9	112.50 (17)
O2—S1—N1	109.61 (9)	N1—C8—H8A	109.1
O3—S1—C1	112.19 (9)	C9—C8—H8A	109.1
O2—S1—C1	112.48 (9)	N1—C8—H8B	109.1
N1—S1—C1	92.39 (9)	C9—C8—H8B	109.1
C7—N1—C8	123.03 (17)	H8A—C8—H8B	107.8
C7—N1—S1	115.60 (14)	O4—C9—C10	122.0 (2)
C8—N1—S1	121.16 (14)	O4—C9—C8	120.45 (19)
C2—C1—C6	122.85 (19)	C10—C9—C8	117.53 (17)
C2—C1—S1	127.02 (16)	C15—C10—C11	119.42 (19)
C6—C1—S1	110.12 (14)	C15—C10—C9	122.54 (19)
C1—C2—C3	116.6 (2)	C11—C10—C9	118.04 (19)
C1—C2—H2	121.7	C12—C11—C10	120.1 (2)
C3—C2—H2	121.7	C12—C11—H11	119.9
C4—C3—C2	121.4 (2)	C10—C11—H11	119.9
C4—C3—H3	119.3	C13—C12—C11	120.1 (2)
C2—C3—H3	119.3	C13—C12—H12	119.9
C3—C4—C5	121.1 (2)	C11—C12—H12	119.9
C3—C4—H4	119.4	C14—C13—C12	120.3 (2)
C5—C4—H4	119.4	C14—C13—H13	119.9
C6—C5—C4	118.1 (2)	C12—C13—H13	119.9
C6—C5—H5	120.9	C13—C14—C15	119.8 (2)
C4—C5—H5	120.9	C13—C14—H14	120.1
C1—C6—C5	119.97 (19)	C15—C14—H14	120.1
C1—C6—C7	113.03 (17)	C10—C15—C14	120.2 (2)
C5—C6—C7	126.91 (19)	C10—C15—H15	119.9
O1—C7—N1	124.10 (19)	C14—C15—H15	119.9
O1—C7—C6	127.35 (19)
O3—S1—N1—C7	109.01 (16)	S1—N1—C7—O1	−177.54 (18)
O2—S1—N1—C7	−120.57 (16)	C8—N1—C7—C6	179.40 (18)
C1—S1—N1—C7	−5.67 (17)	S1—N1—C7—C6	4.5 (2)
O3—S1—N1—C8	−65.95 (18)	C1—C6—C7—O1	−178.4 (2)
O2—S1—N1—C8	64.47 (18)	C5—C6—C7—O1	−1.8 (4)
C1—S1—N1—C8	179.38 (17)	C1—C6—C7—N1	−0.5 (2)
O3—S1—C1—C2	72.9 (2)	C5—C6—C7—N1	176.0 (2)
O2—S1—C1—C2	−62.0 (2)	C7—N1—C8—C9	−77.6 (3)
N1—S1—C1—C2	−174.4 (2)	S1—N1—C8—C9	97.0 (2)
O3—S1—C1—C6	−107.75 (16)	N1—C8—C9—O4	7.7 (3)
O2—S1—C1—C6	117.42 (15)	N1—C8—C9—C10	−175.22 (18)
N1—S1—C1—C6	5.03 (16)	O4—C9—C10—C15	−160.3 (2)
C6—C1—C2—C3	1.2 (3)	C8—C9—C10—C15	22.7 (3)
S1—C1—C2—C3	−179.45 (16)	O4—C9—C10—C11	19.8 (3)
C1—C2—C3—C4	−0.4 (3)	C8—C9—C10—C11	−157.27 (19)
C2—C3—C4—C5	−0.9 (3)	C15—C10—C11—C12	−0.6 (3)
C3—C4—C5—C6	1.4 (3)	C9—C10—C11—C12	179.3 (2)
C2—C1—C6—C5	−0.8 (3)	C10—C11—C12—C13	0.8 (3)
S1—C1—C6—C5	179.80 (16)	C11—C12—C13—C14	0.1 (4)
C2—C1—C6—C7	176.07 (19)	C12—C13—C14—C15	−1.3 (4)
S1—C1—C6—C7	−3.4 (2)	C11—C10—C15—C14	−0.5 (3)
C4—C5—C6—C1	−0.6 (3)	C9—C10—C15—C14	179.5 (2)
C4—C5—C6—C7	−176.9 (2)	C13—C14—C15—C10	1.5 (4)
C8—N1—C7—O1	−2.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1i	0.99	2.41	3.318 (3)	153
C15—H15···O1i	0.95	2.47	3.417 (3)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1i	0.99	2.41	3.318 (3)	153
C15—H15⋯O1i	0.95	2.47	3.417 (3)	178

Symmetry code: (i) .