2-[2-(3-Methoxy-phen-yl)-2-oxoeth-yl]-1,2-benzisothia-zol-3(2H)-one 1,1-dioxide.

In the title compound, C(16)H(13)NO(5)S, the benzothia-zole unit is essentially planar [maximum deviation = 0.0501 (10) Å for the S atom] and is oriented at a dihedral angle of 67.85 (5)° with respect to the meth-oxy-substituted benzene ring. The mean plane of the meth-oxy group is oriented at 14.3 (3)° with respect to the benzene ring to which it is attached. In the crystal structure, weak C-H⋯O hydrogen bonds form macrocyclic rings with R(2) (2)(10) and R(2) (2)(12) 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

C16H13NO5S

M = 331.33

Monoclinic,

a = 8.9824 (3) Å

b = 8.5801 (4) Å

c = 19.5645 (7) Å

β = 97.942 (2)°

V = 1493.37 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 173 K

0.14 × 0.12 × 0.10 mm

Data collection

Nonius diffractometer with Bruker APEXII CCD

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.967, T max = 0.976

15084 measured reflections

3399 independent reflections

2897 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.136

S = 1.06

3399 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.37 e Å−3

Data collection: COLLECT (Nonius, 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/S160053681000543X/lh2991sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000543X/lh2991Isup2.hkl

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

C16H13NO5S	F(000) = 688
Mr = 331.33	Dx = 1.474 Mg m−3
Monoclinic, P21/n	Melting point: 446 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.9824 (3) Å	Cell parameters from 3447 reflections
b = 8.5801 (4) Å	θ = 1.0–27.5°
c = 19.5645 (7) Å	µ = 0.24 mm−1
β = 97.942 (2)°	T = 173 K
V = 1493.37 (10) Å3	Prism, white
Z = 4	0.14 × 0.12 × 0.10 mm

Nonius APEX2 CCD diffractometer	3399 independent reflections
Radiation source: fine-focus sealed tube	2897 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −11→11
Tmin = 0.967, Tmax = 0.976	k = −11→11
15084 measured reflections	l = −25→25

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0682P)2 + 1.0411P] where P = (Fo2 + 2Fc2)/3
3399 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.37 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.

	x	y	z	Uiso*/Ueq
S1	0.22107 (5)	0.29868 (6)	0.10828 (2)	0.02685 (16)
O1	0.03462 (17)	−0.00650 (19)	0.20389 (8)	0.0382 (4)
O2	0.21767 (18)	0.45904 (18)	0.12764 (8)	0.0368 (4)
O3	0.35116 (16)	0.2458 (2)	0.08049 (8)	0.0391 (4)
O4	0.36297 (18)	−0.07414 (19)	0.17637 (8)	0.0417 (4)
O5	0.79500 (17)	0.2056 (2)	0.39967 (9)	0.0431 (4)
N1	0.19250 (18)	0.1858 (2)	0.17480 (9)	0.0284 (4)
C1	0.0523 (2)	0.2394 (2)	0.05901 (10)	0.0270 (4)
C2	−0.0056 (3)	0.2914 (3)	−0.00668 (11)	0.0332 (5)
H2	0.0427	0.3702	−0.0297	0.040*
C3	−0.1387 (3)	0.2208 (3)	−0.03674 (12)	0.0389 (5)
H3	−0.1832	0.2531	−0.0814	0.047*
C4	−0.2074 (2)	0.1051 (3)	−0.00311 (12)	0.0398 (5)
H4	−0.2966	0.0577	−0.0256	0.048*
C5	−0.1486 (2)	0.0565 (3)	0.06313 (12)	0.0355 (5)
H5	−0.1971	−0.0217	0.0865	0.043*
C6	−0.0165 (2)	0.1264 (2)	0.09381 (10)	0.0283 (4)
C7	0.0673 (2)	0.0893 (2)	0.16294 (10)	0.0285 (4)
C8	0.3125 (2)	0.1633 (2)	0.23198 (10)	0.0283 (4)
H8A	0.2684	0.1527	0.2754	0.034*
H8B	0.3787	0.2561	0.2363	0.034*
C9	0.4060 (2)	0.0187 (2)	0.22173 (10)	0.0288 (4)
C10	0.5481 (2)	−0.0057 (2)	0.27013 (10)	0.0264 (4)
C11	0.6073 (2)	0.1091 (2)	0.31602 (10)	0.0282 (4)
H11	0.5553	0.2048	0.3187	0.034*
C12	0.7438 (2)	0.0836 (3)	0.35828 (10)	0.0313 (4)
C13	0.8174 (2)	−0.0582 (3)	0.35630 (11)	0.0403 (6)
H13	0.9093	−0.0765	0.3856	0.048*
C14	0.7554 (3)	−0.1730 (3)	0.31103 (12)	0.0422 (6)
H14	0.8052	−0.2705	0.3101	0.051*
C15	0.6230 (3)	−0.1486 (3)	0.26732 (11)	0.0353 (5)
H15	0.5833	−0.2273	0.2359	0.042*
C16	0.9474 (3)	0.2006 (4)	0.43204 (13)	0.0506 (7)
H16A	0.9728	0.2990	0.4563	0.061*
H16B	1.0139	0.1849	0.3969	0.061*
H16C	0.9601	0.1143	0.4652	0.061*

	U11	U22	U33	U12	U13	U23
S1	0.0282 (3)	0.0253 (3)	0.0253 (2)	−0.00364 (18)	−0.00269 (18)	0.00023 (18)
O1	0.0353 (8)	0.0327 (8)	0.0443 (8)	−0.0046 (6)	−0.0030 (7)	0.0125 (7)
O2	0.0499 (9)	0.0246 (8)	0.0336 (7)	−0.0070 (7)	−0.0030 (7)	−0.0014 (6)
O3	0.0301 (7)	0.0489 (10)	0.0378 (8)	−0.0030 (7)	0.0034 (6)	−0.0015 (7)
O4	0.0422 (9)	0.0365 (9)	0.0421 (9)	0.0039 (7)	−0.0096 (7)	−0.0122 (7)
O5	0.0274 (8)	0.0521 (11)	0.0451 (9)	0.0011 (7)	−0.0117 (7)	−0.0092 (8)
N1	0.0269 (8)	0.0274 (9)	0.0282 (8)	−0.0031 (7)	−0.0056 (7)	0.0039 (7)
C1	0.0284 (9)	0.0232 (9)	0.0270 (9)	0.0035 (8)	−0.0046 (7)	−0.0029 (7)
C2	0.0395 (11)	0.0298 (11)	0.0278 (10)	0.0037 (9)	−0.0045 (8)	−0.0011 (8)
C3	0.0428 (12)	0.0342 (12)	0.0340 (11)	0.0091 (10)	−0.0145 (9)	−0.0054 (9)
C4	0.0314 (10)	0.0313 (12)	0.0505 (13)	0.0060 (9)	−0.0164 (9)	−0.0091 (10)
C5	0.0273 (10)	0.0269 (11)	0.0483 (12)	0.0001 (8)	−0.0080 (9)	−0.0007 (9)
C6	0.0266 (9)	0.0214 (10)	0.0343 (10)	0.0016 (7)	−0.0055 (8)	0.0007 (8)
C7	0.0259 (9)	0.0228 (9)	0.0346 (10)	0.0002 (7)	−0.0031 (8)	0.0020 (8)
C8	0.0276 (9)	0.0289 (10)	0.0253 (9)	0.0032 (8)	−0.0068 (7)	−0.0002 (8)
C9	0.0296 (10)	0.0276 (10)	0.0278 (9)	−0.0004 (8)	−0.0009 (8)	−0.0008 (8)
C10	0.0266 (9)	0.0270 (10)	0.0254 (9)	0.0008 (7)	0.0031 (7)	0.0019 (7)
C11	0.0238 (9)	0.0302 (11)	0.0299 (9)	0.0026 (8)	0.0007 (7)	0.0010 (8)
C12	0.0236 (9)	0.0417 (12)	0.0280 (9)	0.0020 (8)	0.0011 (8)	0.0021 (9)
C13	0.0283 (10)	0.0580 (15)	0.0335 (11)	0.0155 (10)	0.0005 (9)	0.0051 (10)
C14	0.0399 (12)	0.0450 (14)	0.0416 (12)	0.0209 (11)	0.0051 (10)	0.0012 (10)
C15	0.0396 (11)	0.0324 (11)	0.0341 (10)	0.0086 (9)	0.0053 (9)	−0.0009 (9)
C16	0.0268 (11)	0.080 (2)	0.0413 (12)	−0.0054 (11)	−0.0093 (9)	0.0013 (13)

S1—O2	1.4286 (16)	C5—H5	0.9500
S1—O3	1.4291 (16)	C6—C7	1.489 (3)
S1—N1	1.6701 (17)	C8—C9	1.527 (3)
S1—C1	1.7555 (19)	C8—H8A	0.9900
O1—C7	1.212 (2)	C8—H8B	0.9900
O4—C9	1.215 (2)	C9—C10	1.496 (3)
O5—C12	1.364 (3)	C10—C11	1.389 (3)
O5—C16	1.427 (3)	C10—C15	1.403 (3)
N1—C7	1.390 (3)	C11—C12	1.398 (3)
N1—C8	1.455 (2)	C11—H11	0.9500
C1—C6	1.379 (3)	C12—C13	1.388 (3)
C1—C2	1.391 (3)	C13—C14	1.388 (4)
C2—C3	1.396 (3)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.382 (3)
C3—C4	1.383 (4)	C14—H14	0.9500
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.394 (3)	C16—H16A	0.9800
C4—H4	0.9500	C16—H16B	0.9800
C5—C6	1.390 (3)	C16—H16C	0.9800
O2—S1—O3	117.07 (10)	N1—C8—H8A	109.3
O2—S1—N1	109.91 (9)	C9—C8—H8A	109.3
O3—S1—N1	109.52 (9)	N1—C8—H8B	109.3
O2—S1—C1	112.10 (9)	C9—C8—H8B	109.3
O3—S1—C1	112.87 (9)	H8A—C8—H8B	107.9
N1—S1—C1	92.63 (9)	O4—C9—C10	121.86 (19)
C12—O5—C16	117.68 (19)	O4—C9—C8	120.25 (17)
C7—N1—C8	123.05 (17)	C10—C9—C8	117.87 (16)
C7—N1—S1	115.04 (13)	C11—C10—C15	120.17 (19)
C8—N1—S1	119.92 (14)	C11—C10—C9	121.80 (18)
C6—C1—C2	123.07 (19)	C15—C10—C9	118.02 (18)
C6—C1—S1	110.15 (14)	C10—C11—C12	119.80 (19)
C2—C1—S1	126.75 (17)	C10—C11—H11	120.1
C1—C2—C3	116.1 (2)	C12—C11—H11	120.1
C1—C2—H2	122.0	O5—C12—C13	124.50 (19)
C3—C2—H2	122.0	O5—C12—C11	115.27 (19)
C4—C3—C2	121.6 (2)	C13—C12—C11	120.2 (2)
C4—C3—H3	119.2	C12—C13—C14	119.2 (2)
C2—C3—H3	119.2	C12—C13—H13	120.4
C3—C4—C5	121.4 (2)	C14—C13—H13	120.4
C3—C4—H4	119.3	C15—C14—C13	121.5 (2)
C5—C4—H4	119.3	C15—C14—H14	119.2
C6—C5—C4	117.6 (2)	C13—C14—H14	119.2
C6—C5—H5	121.2	C14—C15—C10	119.0 (2)
C4—C5—H5	121.2	C14—C15—H15	120.5
C1—C6—C5	120.31 (19)	C10—C15—H15	120.5
C1—C6—C7	113.22 (17)	O5—C16—H16A	109.5
C5—C6—C7	126.45 (19)	O5—C16—H16B	109.5
O1—C7—N1	123.93 (18)	H16A—C16—H16B	109.5
O1—C7—C6	127.41 (18)	O5—C16—H16C	109.5
N1—C7—C6	108.65 (17)	H16A—C16—H16C	109.5
N1—C8—C9	111.66 (16)	H16B—C16—H16C	109.5
O2—S1—N1—C7	120.14 (16)	S1—N1—C7—C6	−5.4 (2)
O3—S1—N1—C7	−109.92 (16)	C1—C6—C7—O1	−178.6 (2)
C1—S1—N1—C7	5.48 (16)	C5—C6—C7—O1	−0.4 (4)
O2—S1—N1—C8	−75.42 (17)	C1—C6—C7—N1	2.3 (2)
O3—S1—N1—C8	54.52 (17)	C5—C6—C7—N1	−179.5 (2)
C1—S1—N1—C8	169.92 (16)	C7—N1—C8—C9	70.4 (2)
O2—S1—C1—C6	−116.57 (15)	S1—N1—C8—C9	−92.72 (19)
O3—S1—C1—C6	108.65 (16)	N1—C8—C9—O4	−11.3 (3)
N1—S1—C1—C6	−3.83 (16)	N1—C8—C9—C10	170.25 (17)
O2—S1—C1—C2	65.5 (2)	O4—C9—C10—C11	171.5 (2)
O3—S1—C1—C2	−69.3 (2)	C8—C9—C10—C11	−10.0 (3)
N1—S1—C1—C2	178.3 (2)	O4—C9—C10—C15	−7.4 (3)
C6—C1—C2—C3	−0.7 (3)	C8—C9—C10—C15	171.06 (19)
S1—C1—C2—C3	176.93 (17)	C15—C10—C11—C12	1.6 (3)
C1—C2—C3—C4	−0.6 (3)	C9—C10—C11—C12	−177.32 (18)
C2—C3—C4—C5	1.6 (4)	C16—O5—C12—C13	13.8 (3)
C3—C4—C5—C6	−1.2 (3)	C16—O5—C12—C11	−166.2 (2)
C2—C1—C6—C5	1.1 (3)	C10—C11—C12—O5	177.70 (18)
S1—C1—C6—C5	−176.85 (17)	C10—C11—C12—C13	−2.3 (3)
C2—C1—C6—C7	179.45 (19)	O5—C12—C13—C14	−178.9 (2)
S1—C1—C6—C7	1.4 (2)	C11—C12—C13—C14	1.2 (3)
C4—C5—C6—C1	−0.2 (3)	C12—C13—C14—C15	0.8 (4)
C4—C5—C6—C7	−178.2 (2)	C13—C14—C15—C10	−1.5 (4)
C8—N1—C7—O1	11.6 (3)	C11—C10—C15—C14	0.3 (3)
S1—N1—C7—O1	175.52 (17)	C9—C10—C15—C14	179.3 (2)
C8—N1—C7—C6	−169.29 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O5i	0.95	2.53	3.404 (3)	153
C8—H8B···O1ii	0.99	2.42	3.318 (3)	150
C8—H8A···O2i	0.99	2.51	3.301 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O5i	0.95	2.53	3.404 (3)	153
C8—H8B⋯O1ii	0.99	2.42	3.318 (3)	150
C8—H8A⋯O2i	0.99	2.51	3.301 (3)	137

Symmetry codes: (i) ; (ii) .