Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044923/gg2045sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044923/gg2045Isup2.hkl |
CCDC reference: 663807
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
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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
For related literature, see: Groutas et al. (1993, 1996); Güzel & Salman (2006); Siddiqui et al. (2007); Subramanyam et al. (1994).
Crystals of the title compound (I) were grown by slow evaporation from a solution of CHCl3 at 313 K.
Carbon-bound H atoms were included in the refinement at geometrically idealized positions, with C—H = 0.95 and 0.99 Å and Uiso(H) = 1.2Ueq(carrier atom). The final difference map was free of any chemically significant features.
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).
For related literature, see: Groutas et al. (1993, 1996); Güzel & Salman (2006); Siddiqui et al. (2007); Subramanyam et al. (1994).
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).
C8H6ClNO3S | F(000) = 472 |
Mr = 231.65 | Dx = 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 |
Nonius KappaCCD area-detector diffractometer | 2161 independent reflections |
Radiation source: fine-focus sealed tube | 1671 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω and φ scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −11→11 |
Tmin = 0.910, Tmax = 0.965 | k = −11→11 |
4086 measured reflections | l = −16→16 |
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(Fo2) + (0.0437P)2 + 0.6083P] where P = (Fo2 + 2Fc2)/3 |
2161 reflections | (Δ/σ)max < 0.001 |
127 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
C8H6ClNO3S | V = 945.8 (8) Å3 |
Mr = 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)° |
Nonius KappaCCD area-detector diffractometer | 2161 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 1671 reflections with I > 2σ(I) |
Tmin = 0.910, Tmax = 0.965 | Rint = 0.033 |
4086 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.34 e Å−3 |
2161 reflections | Δρmin = −0.40 e Å−3 |
127 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.910, 0.965 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4086, 2161, 1671 |
Rint | 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 |
Δρmax, Δρmin (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).
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. |
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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).