N-Saccharinylmethyl ether.

In the title mol-ecule [systematic name: 1,1,1',1'-tetra-oxo-2,2'-(oxydimethyl-ene)bi(1,2-benzothia-zol-3-one)], C(16)H(12)N(2)O(7)S(2), the benzisothia-zole ring systems are individually planar [maximum deviations of 0.0497 (13) and 0.0195 (19) Å] and their mean planes are inclined at a dihedral angle of 62.76 (4)°. The crystal structure is stabilized by weak inter-molecular C-H⋯O inter-actions. Two O atoms bonded to two S atoms and four aryl H atoms belonging to two symmetry-related mol-ecules lying about an inversion center form a hydrogen-bonded 10-membered ring with graph-set notation R(4) (2)(10).

Related literature

For the biological activity of saccharin derivatives, see: Plath et al. (1998 ▶); Salzburg et al. (1987 ▶); Kapui et al. (2003 ▶). For the synthesis of saccharin derivatives, see: Ahmad et al. (2010 ▶); Siddiqui et al. (2010 ▶). For related structures, see: Ahmad et al. (2009 ▶); Gul et al. (2010 ▶); Khalid et al. (2010 ▶); Siddiqui et al. (2007 ▶, 2008 ▶). For the graph-set notation of hydrogen-bonding patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H12N2O7S2

M = 408.40

Monoclinic,

a = 8.9317 (4) Å

b = 18.3681 (6) Å

c = 10.1942 (5) Å

β = 93.517 (2)°

V = 1669.29 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 200 K

0.08 × 0.06 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.971, T max = 0.986

6489 measured reflections

3756 independent reflections

3052 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.112

S = 1.09

3756 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.42 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/S1600536810010317/lh5013sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010317/lh5013Isup2.hkl

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

C16H12N2O7S2	F(000) = 840
Mr = 408.40	Dx = 1.625 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3299 reflections
a = 8.9317 (4) Å	θ = 1.0–27.4°
b = 18.3681 (6) Å	µ = 0.37 mm−1
c = 10.1942 (5) Å	T = 200 K
β = 93.517 (2)°	Block, colorless
V = 1669.29 (12) Å3	0.08 × 0.06 × 0.04 mm
Z = 4

Nonius KappaCCD diffractometer	3756 independent reflections
Radiation source: fine-focus sealed tube	3052 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω and φ scans	θmax = 27.4°, θmin = 2.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −11→11
Tmin = 0.971, Tmax = 0.986	k = −23→18
6489 measured reflections	l = −13→13

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0212P)2 + 2.3993P] where P = (Fo2 + 2Fc2)/3
3756 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.42 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	0.16733 (7)	0.13166 (4)	0.14038 (7)	0.03295 (17)
S2	0.38728 (7)	0.12529 (3)	0.66150 (6)	0.02728 (15)
O1	0.2772 (2)	0.12845 (12)	0.0444 (2)	0.0478 (5)
O2	0.1836 (2)	0.18787 (11)	0.2374 (2)	0.0429 (5)
O3	−0.0103 (2)	−0.04351 (11)	0.2382 (2)	0.0442 (5)
O4	0.4221 (2)	0.07537 (10)	0.76644 (19)	0.0359 (4)
O5	0.5094 (2)	0.14955 (11)	0.5886 (2)	0.0398 (5)
O6	0.0076 (2)	0.11239 (11)	0.48394 (19)	0.0383 (5)
O7	0.3567 (2)	0.03938 (11)	0.37697 (18)	0.0383 (5)
N1	0.1573 (2)	0.04988 (12)	0.2123 (2)	0.0310 (5)
N2	0.2511 (2)	0.09045 (12)	0.5604 (2)	0.0290 (5)
C1	−0.2366 (3)	0.05097 (15)	0.0789 (3)	0.0346 (6)
H1	−0.2855	0.0083	0.1071	0.042*
C2	−0.3127 (3)	0.10214 (17)	0.0004 (3)	0.0411 (7)
H2	−0.4159	0.0948	−0.0245	0.049*
C3	−0.2408 (4)	0.16386 (17)	−0.0425 (3)	0.0438 (7)
H3	−0.2948	0.1972	−0.0988	0.053*
C4	−0.0923 (3)	0.17795 (15)	−0.0053 (3)	0.0383 (6)
H4	−0.0437	0.2208	−0.0328	0.046*
C5	−0.0177 (3)	0.12689 (14)	0.0738 (3)	0.0291 (5)
C6	−0.0865 (3)	0.06398 (13)	0.1153 (3)	0.0278 (5)
C7	0.0161 (3)	0.01604 (14)	0.1959 (3)	0.0302 (5)
C8	0.2930 (3)	0.01150 (16)	0.2583 (3)	0.0381 (7)
H8A	0.2690	−0.0406	0.2702	0.046*
H8B	0.3673	0.0149	0.1904	0.046*
C9	0.0236 (3)	0.24265 (15)	0.6728 (3)	0.0340 (6)
H9	−0.0741	0.2401	0.6307	0.041*
C10	0.0619 (3)	0.29787 (15)	0.7627 (3)	0.0381 (6)
H10	−0.0114	0.3329	0.7828	0.046*
C11	0.2047 (3)	0.30251 (15)	0.8233 (3)	0.0358 (6)
H11	0.2281	0.3411	0.8831	0.043*
C12	0.3143 (3)	0.25158 (14)	0.7980 (3)	0.0342 (6)
H12	0.4124	0.2543	0.8393	0.041*
C13	0.2738 (3)	0.19682 (14)	0.7098 (3)	0.0281 (5)
C14	0.1321 (3)	0.19172 (14)	0.6466 (2)	0.0282 (5)
C15	0.1155 (3)	0.12903 (14)	0.5542 (2)	0.0284 (5)
C16	0.2762 (3)	0.02374 (14)	0.4899 (3)	0.0331 (6)
H16A	0.3342	−0.0108	0.5477	0.040*
H16B	0.1788	0.0009	0.4628	0.040*

	U11	U22	U33	U12	U13	U23
S1	0.0283 (3)	0.0322 (3)	0.0387 (4)	−0.0050 (3)	0.0046 (3)	−0.0050 (3)
S2	0.0211 (3)	0.0322 (3)	0.0282 (3)	0.0023 (2)	−0.0006 (2)	−0.0019 (3)
O1	0.0381 (11)	0.0540 (13)	0.0533 (14)	−0.0084 (10)	0.0177 (10)	−0.0029 (11)
O2	0.0383 (11)	0.0362 (10)	0.0539 (13)	−0.0069 (9)	0.0005 (10)	−0.0149 (10)
O3	0.0501 (12)	0.0346 (10)	0.0474 (13)	−0.0041 (9)	−0.0018 (10)	0.0132 (9)
O4	0.0347 (10)	0.0398 (10)	0.0324 (10)	0.0094 (8)	−0.0047 (8)	0.0011 (8)
O5	0.0256 (9)	0.0499 (12)	0.0447 (12)	−0.0026 (8)	0.0081 (8)	−0.0036 (10)
O6	0.0296 (9)	0.0494 (11)	0.0347 (11)	0.0017 (8)	−0.0086 (8)	0.0000 (9)
O7	0.0296 (10)	0.0552 (12)	0.0295 (10)	0.0028 (9)	−0.0031 (8)	−0.0124 (9)
N1	0.0264 (11)	0.0316 (11)	0.0342 (12)	0.0032 (9)	−0.0036 (9)	−0.0028 (10)
N2	0.0243 (10)	0.0346 (11)	0.0274 (11)	0.0034 (9)	−0.0029 (8)	−0.0040 (9)
C1	0.0313 (13)	0.0371 (14)	0.0348 (15)	−0.0031 (11)	−0.0024 (11)	−0.0061 (12)
C2	0.0336 (14)	0.0521 (17)	0.0358 (15)	0.0082 (13)	−0.0112 (12)	−0.0132 (13)
C3	0.0567 (19)	0.0400 (16)	0.0335 (16)	0.0168 (14)	−0.0064 (14)	−0.0013 (13)
C4	0.0509 (17)	0.0316 (13)	0.0327 (15)	0.0032 (12)	0.0043 (13)	0.0036 (12)
C5	0.0295 (13)	0.0292 (12)	0.0287 (13)	0.0000 (10)	0.0025 (10)	−0.0010 (10)
C6	0.0274 (12)	0.0270 (12)	0.0285 (13)	0.0005 (10)	−0.0008 (10)	−0.0029 (10)
C7	0.0335 (13)	0.0297 (12)	0.0270 (13)	0.0009 (11)	−0.0023 (11)	−0.0024 (11)
C8	0.0315 (14)	0.0471 (16)	0.0345 (15)	0.0121 (12)	−0.0083 (12)	−0.0124 (13)
C9	0.0281 (13)	0.0375 (14)	0.0366 (15)	0.0058 (11)	0.0047 (11)	0.0064 (12)
C10	0.0405 (15)	0.0341 (14)	0.0406 (16)	0.0108 (12)	0.0090 (13)	0.0031 (12)
C11	0.0431 (15)	0.0312 (13)	0.0339 (14)	0.0012 (11)	0.0081 (12)	−0.0028 (11)
C12	0.0340 (14)	0.0346 (13)	0.0341 (15)	−0.0026 (11)	0.0041 (12)	−0.0026 (12)
C13	0.0229 (11)	0.0323 (12)	0.0296 (13)	0.0021 (10)	0.0046 (10)	0.0020 (11)
C14	0.0272 (12)	0.0311 (12)	0.0266 (13)	0.0007 (10)	0.0036 (10)	0.0073 (10)
C15	0.0255 (12)	0.0341 (13)	0.0256 (12)	0.0022 (10)	0.0019 (10)	0.0060 (11)
C16	0.0328 (13)	0.0329 (13)	0.0332 (14)	−0.0004 (11)	−0.0017 (11)	−0.0032 (11)

S1—O1	1.429 (2)	C3—C4	1.382 (4)
S1—O2	1.431 (2)	C3—H3	0.9500
S1—N1	1.676 (2)	C4—C5	1.381 (4)
S1—C5	1.750 (3)	C4—H4	0.9500
S2—O5	1.4280 (19)	C5—C6	1.387 (3)
S2—O4	1.4287 (19)	C6—C7	1.482 (3)
S2—N2	1.673 (2)	C8—H8A	0.9900
S2—C13	1.748 (2)	C8—H8B	0.9900
O3—C7	1.205 (3)	C9—C14	1.384 (3)
O6—C15	1.205 (3)	C9—C10	1.396 (4)
O7—C8	1.402 (3)	C9—H9	0.9500
O7—C16	1.424 (3)	C10—C11	1.385 (4)
N1—C7	1.407 (3)	C10—H10	0.9500
N1—C8	1.454 (3)	C11—C12	1.390 (4)
N2—C15	1.401 (3)	C11—H11	0.9500
N2—C16	1.445 (3)	C12—C13	1.382 (4)
C1—C2	1.386 (4)	C12—H12	0.9500
C1—C6	1.390 (3)	C13—C14	1.388 (3)
C1—H1	0.9500	C14—C15	1.489 (4)
C2—C3	1.387 (5)	C16—H16A	0.9900
C2—H2	0.9500	C16—H16B	0.9900
O1—S1—O2	117.27 (13)	O3—C7—N1	123.5 (2)
O1—S1—N1	108.66 (12)	O3—C7—C6	127.6 (2)
O2—S1—N1	110.47 (12)	N1—C7—C6	108.8 (2)
O1—S1—C5	113.86 (13)	O7—C8—N1	112.8 (2)
O2—S1—C5	110.97 (12)	O7—C8—H8A	109.0
N1—S1—C5	92.88 (11)	N1—C8—H8A	109.0
O5—S2—O4	116.83 (12)	O7—C8—H8B	109.0
O5—S2—N2	110.41 (12)	N1—C8—H8B	109.0
O4—S2—N2	109.43 (12)	H8A—C8—H8B	107.8
O5—S2—C13	112.74 (12)	C14—C9—C10	118.1 (3)
O4—S2—C13	112.00 (12)	C14—C9—H9	120.9
N2—S2—C13	92.81 (11)	C10—C9—H9	120.9
C8—O7—C16	115.2 (2)	C11—C10—C9	121.3 (3)
C7—N1—C8	123.2 (2)	C11—C10—H10	119.4
C7—N1—S1	114.55 (17)	C9—C10—H10	119.4
C8—N1—S1	120.62 (19)	C10—C11—C12	121.0 (3)
C15—N2—C16	124.5 (2)	C10—C11—H11	119.5
C15—N2—S2	115.34 (17)	C12—C11—H11	119.5
C16—N2—S2	120.12 (17)	C13—C12—C11	116.8 (3)
C2—C1—C6	117.9 (3)	C13—C12—H12	121.6
C2—C1—H1	121.0	C11—C12—H12	121.6
C6—C1—H1	121.0	C12—C13—C14	123.1 (2)
C1—C2—C3	121.1 (3)	C12—C13—S2	126.7 (2)
C1—C2—H2	119.5	C14—C13—S2	110.25 (19)
C3—C2—H2	119.5	C9—C14—C13	119.6 (2)
C4—C3—C2	121.5 (3)	C9—C14—C15	126.9 (2)
C4—C3—H3	119.3	C13—C14—C15	113.5 (2)
C2—C3—H3	119.3	O6—C15—N2	123.8 (2)
C5—C4—C3	117.0 (3)	O6—C15—C14	128.1 (2)
C5—C4—H4	121.5	N2—C15—C14	108.1 (2)
C3—C4—H4	121.5	O7—C16—N2	109.4 (2)
C4—C5—C6	122.5 (2)	O7—C16—H16A	109.8
C4—C5—S1	127.1 (2)	N2—C16—H16A	109.8
C6—C5—S1	110.41 (19)	O7—C16—H16B	109.8
C5—C6—C1	120.0 (2)	N2—C16—H16B	109.8
C5—C6—C7	113.2 (2)	H16A—C16—H16B	108.2
C1—C6—C7	126.8 (2)
O1—S1—N1—C7	−118.8 (2)	C1—C6—C7—O3	3.8 (5)
O2—S1—N1—C7	111.19 (19)	C5—C6—C7—N1	2.2 (3)
C5—S1—N1—C7	−2.5 (2)	C1—C6—C7—N1	−178.7 (2)
O1—S1—N1—C8	47.0 (2)	C16—O7—C8—N1	71.9 (3)
O2—S1—N1—C8	−83.0 (2)	C7—N1—C8—O7	−118.3 (3)
C5—S1—N1—C8	163.4 (2)	S1—N1—C8—O7	77.1 (3)
O5—S2—N2—C15	−114.79 (19)	C14—C9—C10—C11	0.8 (4)
O4—S2—N2—C15	115.27 (19)	C9—C10—C11—C12	−1.0 (4)
C13—S2—N2—C15	0.8 (2)	C10—C11—C12—C13	0.2 (4)
O5—S2—N2—C16	67.1 (2)	C11—C12—C13—C14	0.8 (4)
O4—S2—N2—C16	−62.9 (2)	C11—C12—C13—S2	−179.1 (2)
C13—S2—N2—C16	−177.4 (2)	O5—S2—C13—C12	−66.3 (3)
C6—C1—C2—C3	1.1 (4)	O4—S2—C13—C12	67.9 (3)
C1—C2—C3—C4	−2.2 (4)	N2—S2—C13—C12	−179.8 (2)
C2—C3—C4—C5	1.6 (4)	O5—S2—C13—C14	113.83 (19)
C3—C4—C5—C6	−0.1 (4)	O4—S2—C13—C14	−111.97 (19)
C3—C4—C5—S1	−177.6 (2)	N2—S2—C13—C14	0.3 (2)
O1—S1—C5—C4	−66.8 (3)	C10—C9—C14—C13	0.1 (4)
O2—S1—C5—C4	68.1 (3)	C10—C9—C14—C15	−179.7 (2)
N1—S1—C5—C4	−178.6 (3)	C12—C13—C14—C9	−0.9 (4)
O1—S1—C5—C6	115.5 (2)	S2—C13—C14—C9	179.0 (2)
O2—S1—C5—C6	−109.6 (2)	C12—C13—C14—C15	178.9 (2)
N1—S1—C5—C6	3.7 (2)	S2—C13—C14—C15	−1.2 (3)
C4—C5—C6—C1	−0.9 (4)	C16—N2—C15—O6	−3.9 (4)
S1—C5—C6—C1	176.9 (2)	S2—N2—C15—O6	178.1 (2)
C4—C5—C6—C7	178.2 (2)	C16—N2—C15—C14	176.5 (2)
S1—C5—C6—C7	−3.9 (3)	S2—N2—C15—C14	−1.5 (3)
C2—C1—C6—C5	0.4 (4)	C9—C14—C15—O6	2.0 (4)
C2—C1—C6—C7	−178.6 (3)	C13—C14—C15—O6	−177.8 (3)
C8—N1—C7—O3	12.8 (4)	C9—C14—C15—N2	−178.5 (2)
S1—N1—C7—O3	178.2 (2)	C13—C14—C15—N2	1.7 (3)
C8—N1—C7—C6	−164.8 (2)	C8—O7—C16—N2	−128.4 (2)
S1—N1—C7—C6	0.6 (3)	C15—N2—C16—O7	101.2 (3)
C5—C6—C7—O3	−175.2 (3)	S2—N2—C16—O7	−80.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O4i	0.95	2.39	3.307 (4)	162
C2—H2···O4ii	0.95	2.53	3.293 (3)	138
C8—H8B···O4iii	0.99	2.52	3.027 (3)	111
C8—H8A···O3	0.99	2.50	2.887 (4)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O4i	0.95	2.39	3.307 (4)	162
C2—H2⋯O4ii	0.95	2.53	3.293 (3)	138
C8—H8B⋯O4iii	0.99	2.52	3.027 (3)	111

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