2-Chloro­methyl-1,2-benzisothia­zole-1,1,3(2H)-trione

Siddiqui, W.A.; Ahmad, S.; Khan, I.U.; Siddiqui, H.L.; Parvez, M.

doi:10.1107/S1600536807044923

2-Chloromethyl-1,2-benzisothiazole-1,1,3(2H)-trione

W. A. Siddiqui, S. Ahmad, I. U. Khan, H. L. Siddiqui and M. Parvez

The molecule of the title compound, C₈H₆ClNO₃S, contains a planar benzisothiazole ring system. The crystal structure is stabilized by C—H

O intermolecular interactions, with C

O distances of 3.222 (3) and 3.288 (3) Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044923/gg2045sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044923/gg2045Isup2.hkl Contains datablock I

CCDC reference: 663807

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R factor = 0.039
wR factor = 0.102
Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  O2     ..  C7      ..       2.85 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Saccharin derivatives have been reported as important biological agents in the treatment of a wide range of diseases for many years (Subramanyam et al., 1994; Groutas et al., 1996; Güzel & Salman, 2006). Chloromethylsaccharin being one of the saccharin derivatives available has already been tested for its activity as human leucocyte elastase (HLE) inhibitor (Groutas et al., 1993). In our recent work we have reported the title compound (I) as an important intermediate in the synthesis of 1,2-benzothiazine 1,1-dioxide derivatives belonging to the oxicam class of non-steroidal anti-inflammatory drugs (NSAIDs) (Siddiqui et al., 2007). Herein, we report the structure of the title compound (I).

In the structure (Fig. 1) the benzisothiazole ring system is essentially planar; the maximum deviation of any atom from the mean plane through S1/O1/N1/C1–C7 being 0.029 (1) Å for S1 and C7 atoms. The molecules are linked via weak C—H···O type hydrogen bonds, thus stabilizing the crystal structure (Fig. 2).

Related literature top

For related literature, see: Groutas et al. (1993, 1996); Güzel & Salman (2006); Siddiqui et al. (2007); Subramanyam et al. (1994).

Experimental top

Crystals of the title compound (I) were grown by slow evaporation from a solution of CHCl₃ at 313 K.

Structure description top

For related literature, see: Groutas et al. (1993, 1996); Güzel & Salman (2006); Siddiqui et al. (2007); Subramanyam et al. (1994).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL 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, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Unit cell packing of the title compound (I), showing the C—H···O interactions as dashed lines.

2-Chloromethyl-1,2-benzisothiazole-1,1,3(2H)-trione top

Crystal data top

C₈H₆ClNO₃S	F(000) = 472
M_r = 231.65	D_x = 1.627 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4086 reflections
a = 9.208 (5) Å	θ = 3.3–27.5°
b = 8.643 (4) Å	µ = 0.60 mm⁻¹
c = 12.458 (6) Å	T = 173 K
β = 107.46 (2)°	Prism, colourless
V = 945.8 (8) Å³	0.16 × 0.10 × 0.06 mm
Z = 4

Data collection top

Nonius KappaCCD area-detector diffractometer	2161 independent reflections
Radiation source: fine-focus sealed tube	1671 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω and φ scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −11→11
T_min = 0.910, T_max = 0.965	k = −11→11
4086 measured reflections	l = −16→16

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0437P)² + 0.6083P] where P = (F_o² + 2F_c²)/3
2161 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₈H₆ClNO₃S	V = 945.8 (8) Å³
M_r = 231.65	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.208 (5) Å	µ = 0.60 mm⁻¹
b = 8.643 (4) Å	T = 173 K
c = 12.458 (6) Å	0.16 × 0.10 × 0.06 mm
β = 107.46 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	2161 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	1671 reflections with I > 2σ(I)
T_min = 0.910, T_max = 0.965	R_int = 0.033
4086 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	Δρ_max = 0.34 e Å⁻³
2161 reflections	Δρ_min = −0.40 e Å⁻³
127 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.13760 (9)	0.96958 (7)	−0.09257 (6)	0.0450 (2)
S1	0.21025 (6)	0.61766 (6)	0.09596 (4)	0.02421 (16)
O1	0.17085 (19)	0.58867 (19)	−0.21198 (12)	0.0307 (4)
O2	0.07883 (19)	0.5821 (2)	0.13012 (13)	0.0349 (4)
O3	0.31276 (19)	0.73035 (19)	0.16087 (12)	0.0311 (4)
N1	0.1551 (2)	0.6681 (2)	−0.03988 (14)	0.0243 (4)
C1	0.3062 (3)	0.4538 (2)	0.07062 (17)	0.0236 (5)
C2	0.3863 (3)	0.3462 (3)	0.14818 (19)	0.0320 (6)
H2	0.3917	0.3532	0.2254	0.038*
C3	0.4585 (3)	0.2278 (3)	0.1091 (2)	0.0359 (6)
H3	0.5138	0.1517	0.1602	0.043*
C4	0.4512 (3)	0.2185 (3)	−0.0042 (2)	0.0345 (6)
H4	0.5030	0.1372	−0.0286	0.041*
C5	0.3699 (3)	0.3257 (3)	−0.08149 (19)	0.0280 (5)
H5	0.3646	0.3186	−0.1587	0.034*
C6	0.2963 (3)	0.4440 (2)	−0.04326 (17)	0.0226 (5)
C7	0.2032 (3)	0.5687 (3)	−0.11165 (17)	0.0234 (5)
C8	0.0460 (3)	0.7888 (3)	−0.08138 (19)	0.0296 (5)
H8A	−0.0169	0.8017	−0.0300	0.036*
H8B	−0.0224	0.7593	−0.1563	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0490 (5)	0.0296 (3)	0.0581 (4)	0.0029 (3)	0.0184 (3)	0.0067 (3)
S1	0.0253 (3)	0.0299 (3)	0.0174 (3)	−0.0027 (2)	0.0063 (2)	−0.0028 (2)
O1	0.0385 (10)	0.0359 (9)	0.0182 (7)	0.0017 (8)	0.0092 (7)	0.0021 (7)
O2	0.0295 (10)	0.0503 (10)	0.0292 (8)	−0.0062 (8)	0.0153 (7)	−0.0047 (8)
O3	0.0318 (10)	0.0349 (9)	0.0238 (8)	−0.0067 (8)	0.0042 (7)	−0.0086 (7)
N1	0.0269 (11)	0.0276 (9)	0.0174 (8)	0.0026 (8)	0.0053 (7)	−0.0009 (7)
C1	0.0247 (12)	0.0234 (11)	0.0228 (10)	−0.0038 (9)	0.0073 (9)	0.0001 (9)
C2	0.0333 (14)	0.0353 (13)	0.0257 (11)	−0.0050 (11)	0.0059 (10)	0.0079 (10)
C3	0.0353 (15)	0.0259 (11)	0.0430 (14)	−0.0004 (11)	0.0064 (11)	0.0102 (11)
C4	0.0319 (14)	0.0232 (11)	0.0514 (15)	−0.0001 (11)	0.0171 (12)	0.0008 (11)
C5	0.0291 (13)	0.0273 (11)	0.0299 (11)	−0.0041 (10)	0.0122 (10)	−0.0033 (9)
C6	0.0208 (12)	0.0234 (10)	0.0236 (10)	−0.0048 (9)	0.0066 (9)	0.0001 (9)
C7	0.0250 (12)	0.0256 (10)	0.0203 (10)	−0.0030 (9)	0.0081 (9)	−0.0004 (8)
C8	0.0272 (13)	0.0307 (12)	0.0281 (11)	0.0039 (10)	0.0038 (10)	−0.0004 (10)

Geometric parameters (Å, º) top

Cl1—C8	1.801 (3)	C2—H2	0.9500
S1—O3	1.427 (2)	C3—C4	1.394 (4)
S1—O2	1.431 (2)	C3—H3	0.9500
S1—N1	1.672 (2)	C4—C5	1.384 (3)
S1—C1	1.748 (2)	C4—H4	0.9500
O1—C7	1.207 (3)	C5—C6	1.387 (3)
N1—C7	1.404 (3)	C5—H5	0.9500
N1—C8	1.433 (3)	C6—C7	1.478 (3)
C1—C2	1.384 (3)	C8—H8A	0.9900
C1—C6	1.397 (3)	C8—H8B	0.9900
C2—C3	1.386 (4)

O3—S1—O2	116.90 (10)	C5—C4—C3	121.2 (2)
O3—S1—N1	110.12 (10)	C5—C4—H4	119.4
O2—S1—N1	109.25 (10)	C3—C4—H4	119.4
O3—S1—C1	111.79 (11)	C4—C5—C6	118.2 (2)
O2—S1—C1	113.48 (11)	C4—C5—H5	120.9
N1—S1—C1	92.56 (10)	C6—C5—H5	120.9
C7—N1—C8	122.46 (18)	C5—C6—C1	120.2 (2)
C7—N1—S1	115.29 (15)	C5—C6—C7	126.72 (19)
C8—N1—S1	121.46 (15)	C1—C6—C7	113.05 (19)
C2—C1—C6	121.8 (2)	O1—C7—N1	123.0 (2)
C2—C1—S1	127.66 (18)	O1—C7—C6	128.4 (2)
C6—C1—S1	110.49 (16)	N1—C7—C6	108.55 (17)
C3—C2—C1	117.5 (2)	N1—C8—Cl1	111.45 (17)
C3—C2—H2	121.2	N1—C8—H8A	109.3
C1—C2—H2	121.2	Cl1—C8—H8A	109.3
C2—C3—C4	121.0 (2)	N1—C8—H8B	109.3
C2—C3—H3	119.5	Cl1—C8—H8B	109.3
C4—C3—H3	119.5	H8A—C8—H8B	108.0

O3—S1—N1—C7	114.39 (17)	C4—C5—C6—C1	0.6 (3)
O2—S1—N1—C7	−115.93 (17)	C4—C5—C6—C7	−179.5 (2)
C1—S1—N1—C7	0.05 (18)	C2—C1—C6—C5	−1.1 (3)
O3—S1—N1—C8	−75.6 (2)	S1—C1—C6—C5	177.41 (18)
O2—S1—N1—C8	54.1 (2)	C2—C1—C6—C7	178.9 (2)
C1—S1—N1—C8	170.05 (18)	S1—C1—C6—C7	−2.5 (2)
O3—S1—C1—C2	67.0 (2)	C8—N1—C7—O1	9.2 (3)
O2—S1—C1—C2	−67.8 (2)	S1—N1—C7—O1	179.07 (18)
N1—S1—C1—C2	179.9 (2)	C8—N1—C7—C6	−171.3 (2)
O3—S1—C1—C6	−111.42 (17)	S1—N1—C7—C6	−1.4 (2)
O2—S1—C1—C6	113.75 (17)	C5—C6—C7—O1	2.1 (4)
N1—S1—C1—C6	1.45 (18)	C1—C6—C7—O1	−178.0 (2)
C6—C1—C2—C3	0.6 (3)	C5—C6—C7—N1	−177.4 (2)
S1—C1—C2—C3	−177.65 (19)	C1—C6—C7—N1	2.5 (3)
C1—C2—C3—C4	0.4 (4)	C7—N1—C8—Cl1	−93.0 (2)
C2—C3—C4—C5	−1.0 (4)	S1—N1—C8—Cl1	97.72 (18)
C3—C4—C5—C6	0.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.95	2.52	3.222 (3)	131
C8—H8B···O3ⁱⁱ	0.99	2.33	3.288 (3)	163

Symmetry codes: (i) −x+1/2, y−1/2, −z−1/2; (ii) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₈H₆ClNO₃S
M_r	231.65
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.208 (5), 8.643 (4), 12.458 (6)
β (°)	107.46 (2)
V (Å³)	945.8 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.16 × 0.10 × 0.06

Data collection
Diffractometer	Nonius KappaCCD area-detector
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.910, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	4086, 2161, 1671
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.102, 1.03
No. of reflections	2161
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.40

Computer programs: COLLECT (Nonius, 1998), HKL DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).