3-(Propan-2-yl­oxy)-1,2-benzothia­zole 1,1-dioxide

Khan, M.H.; Khan, I.U.; Mughal, S.Y.; Akkurt, M.

doi:10.1107/S1600536812002413

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o507

doi:10.1107/S1600536812002413

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3-(Propan-2-yloxy)-1,2-benzothiazole 1,1-dioxide

Muneeb Hayat Khan,^a Islam Ullah Khan,^a Shumaila Younas Mughal ^a and Mehmet Akkurt ^b ^*

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 6 January 2012; accepted 19 January 2012; online 25 January 2012)

In the title compound, C₁₀H₁₁NO₃S, the benzisothiazole ring system is almost planar [maximum deviation = 0.030 (1) Å for the S atom]. The isopropoxy group is almost in the plane of the benzisothiazole ring system [N—C—O—C = 4.5 (2)°] with one of its methyl groups in an antiperiplanar orientation relative to the benzisothiazole ring system [C—C—O—C = −162.0 (2)°].

Related literature

For related structures, see: Siddiqui et al. (2007 , 2008 ); Bassin et al. (2011 ); Arshad et al. (2009a ,b ).

Experimental

Crystal data

C₁₀H₁₁NO₃S
M_r = 225.27
Triclinic, $[P \overline 1]$
a = 8.1899 (3) Å
b = 8.8361 (4) Å
c = 8.9045 (4) Å
α = 101.624 (2)°
β = 106.694 (1)°
γ = 114.898 (1)°
V = 519.89 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 296 K
0.13 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
9516 measured reflections
2560 independent reflections
2090 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.102
S = 1.05
2560 reflections
138 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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: WinGX (Farrugia, 1999 ), PARST (Nardelli, 1983 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812002413/ld2045sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002413/ld2045Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812002413/ld2045Isup3.cml

checkCIF report

Comment top

The title compound (I) was prepared while synthesizing benzisothiazoles from sodium saccharin. Slight increase in the reaction temperature from 333 K to 353 K give rise to the unexpected product instead of a benzisothiazole derivative.

In the title molecule (Fig. 1), the S atom has a distorted tetrahedral coordination geometry, with S1—O1 = 1.4278 (15), S1—O2 = 1.4264 (16), S1— N1 = 1.6493 (14), S1—C1 = 1.7642 (19) Å, O1—S1—O2 = 117.54 (9), O1—S1—N1 = 109.42 (8), O1—S1—C1 = 110.06 (9), O2—S1—N1 = 109.04 (8), O2—S1—C1 = 112.19 (9) and N1— S1—C1 = 96.54 (8)°. The values of the geometric parameters are in agreement with those observed in related compounds (Siddiqui et al., 2007; Bassin et al., 2011; Arshad et al., 2009a,b; Siddiqui et al., 2008).

Related literature top

For related structures, see: Siddiqui et al. (2007, 2008); Bassin et al. (2011); Arshad et al. (2009a,b).

Experimental top

Sodium saccharin (0.5 g m, 2.439 mmol) was placed in a 50 ml round-bottom flask, and 20 ml of the dried DMF were added to it. The mixture was stirred for 5 min. Then iso-propyl iodide (0.243 ml, 2.439 mmol) was added and the mixture was placed under reflux for 3 h at 353 K. After that, the reaction mixture was poured in ice. The precipitate was filtered, washed with ice-cold water, dried and recrystallized from methanol.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: WinGX (Farrugia, 1999), PARST (Nardelli, 1983) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of the molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.

3-(Propan-2-yloxy)-1,2-benzothiazole 1,1-dioxide top

Crystal data top

C₁₀H₁₁NO₃S	Z = 2
M_r = 225.27	F(000) = 236
Triclinic, P1	D_x = 1.439 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1899 (3) Å	Cell parameters from 4072 reflections
b = 8.8361 (4) Å	θ = 2.6–28.0°
c = 8.9045 (4) Å	µ = 0.30 mm⁻¹
α = 101.624 (2)°	T = 296 K
β = 106.694 (1)°	Prism, colourless
γ = 114.898 (1)°	0.13 × 0.10 × 0.08 mm
V = 519.89 (4) Å³

Data collection top

Bruker APEXII CCD diffractometer	2090 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 28.4°, θ_min = 2.7°
ϕ and ω scans	h = −10→10
9516 measured reflections	k = −11→11
2560 independent reflections	l = −11→11

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0509P)² + 0.1198P] where P = (F_o² + 2F_c²)/3
2560 reflections	(Δ/σ)_max < 0.001
138 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₀H₁₁NO₃S	γ = 114.898 (1)°
M_r = 225.27	V = 519.89 (4) Å³
Triclinic, P1	Z = 2
a = 8.1899 (3) Å	Mo Kα radiation
b = 8.8361 (4) Å	µ = 0.30 mm⁻¹
c = 8.9045 (4) Å	T = 296 K
α = 101.624 (2)°	0.13 × 0.10 × 0.08 mm
β = 106.694 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2090 reflections with I > 2σ(I)
9516 measured reflections	R_int = 0.020
2560 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.05	Δρ_max = 0.29 e Å⁻³
2560 reflections	Δρ_min = −0.34 e Å⁻³
138 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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.

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

	x	y	z	U_iso*/U_eq
S1	0.51553 (5)	0.65330 (5)	−0.19102 (5)	0.0414 (1)
O1	0.4815 (2)	0.7249 (2)	−0.31926 (16)	0.0625 (5)
O2	0.35943 (17)	0.48322 (17)	−0.21499 (18)	0.0616 (4)
O3	0.85768 (15)	0.97134 (14)	0.24607 (13)	0.0389 (3)
N1	0.58062 (18)	0.80108 (18)	−0.00718 (16)	0.0386 (4)
C1	0.7438 (2)	0.6603 (2)	−0.14202 (18)	0.0347 (4)
C2	0.8040 (2)	0.5704 (2)	−0.2379 (2)	0.0423 (5)
C3	0.9986 (3)	0.6115 (2)	−0.1638 (2)	0.0472 (6)
C4	1.1264 (2)	0.7379 (2)	−0.0035 (2)	0.0470 (6)
C5	1.0640 (2)	0.8267 (2)	0.0923 (2)	0.0402 (5)
C6	0.8694 (2)	0.78493 (19)	0.02064 (18)	0.0325 (4)
C7	0.7613 (2)	0.85598 (19)	0.08991 (18)	0.0333 (4)
C8	0.7475 (2)	1.0339 (2)	0.3210 (2)	0.0418 (5)
C9	0.9032 (3)	1.2032 (3)	0.4722 (2)	0.0561 (6)
C10	0.6175 (3)	0.8887 (3)	0.3664 (3)	0.0610 (7)
H2	0.71820	0.48640	−0.34680	0.0510*
H3	1.04400	0.55220	−0.22400	0.0570*
H4	1.25700	0.76420	0.04130	0.0560*
H5	1.15010	0.91140	0.20090	0.0480*
H8	0.66590	1.06130	0.23960	0.0500*
H9A	0.98120	1.17530	0.55260	0.0840*
H9B	0.84010	1.25380	0.52320	0.0840*
H9C	0.98750	1.28810	0.43690	0.0840*
H10A	0.53260	0.77990	0.26810	0.0910*
H10B	0.53830	0.92470	0.40760	0.0910*
H10C	0.69860	0.86850	0.45240	0.0910*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0302 (2)	0.0471 (2)	0.0359 (2)	0.0212 (2)	0.0067 (2)	0.0023 (2)
O1	0.0688 (9)	0.0846 (10)	0.0389 (7)	0.0538 (8)	0.0105 (6)	0.0162 (7)
O2	0.0311 (6)	0.0500 (7)	0.0705 (9)	0.0097 (5)	0.0136 (6)	−0.0036 (6)
O3	0.0344 (5)	0.0448 (6)	0.0316 (5)	0.0210 (5)	0.0112 (4)	0.0054 (4)
N1	0.0319 (6)	0.0444 (7)	0.0358 (7)	0.0225 (6)	0.0112 (5)	0.0055 (5)
C1	0.0307 (7)	0.0378 (8)	0.0358 (7)	0.0185 (6)	0.0146 (6)	0.0110 (6)
C2	0.0446 (8)	0.0425 (8)	0.0403 (8)	0.0232 (7)	0.0208 (7)	0.0095 (7)
C3	0.0496 (9)	0.0551 (10)	0.0560 (10)	0.0350 (8)	0.0335 (8)	0.0211 (8)
C4	0.0359 (8)	0.0632 (11)	0.0544 (10)	0.0311 (8)	0.0231 (7)	0.0256 (9)
C5	0.0316 (7)	0.0491 (9)	0.0385 (8)	0.0205 (7)	0.0138 (6)	0.0149 (7)
C6	0.0303 (7)	0.0364 (7)	0.0336 (7)	0.0179 (6)	0.0154 (6)	0.0133 (6)
C7	0.0319 (7)	0.0345 (7)	0.0326 (7)	0.0177 (6)	0.0130 (6)	0.0099 (6)
C8	0.0444 (8)	0.0458 (9)	0.0352 (8)	0.0281 (7)	0.0147 (7)	0.0062 (7)
C9	0.0649 (12)	0.0509 (10)	0.0402 (9)	0.0286 (9)	0.0160 (8)	0.0048 (8)
C10	0.0610 (11)	0.0629 (12)	0.0602 (12)	0.0292 (10)	0.0367 (10)	0.0139 (10)

Geometric parameters (Å, º) top

S1—O1	1.4278 (15)	C8—C9	1.508 (3)
S1—O2	1.4264 (16)	C8—C10	1.500 (3)
S1—N1	1.6493 (14)	C2—H2	0.9300
S1—C1	1.7642 (19)	C3—H3	0.9300
O3—C7	1.3101 (18)	C4—H4	0.9300
O3—C8	1.477 (2)	C5—H5	0.9300
N1—C7	1.290 (2)	C8—H8	0.9800
C1—C2	1.379 (2)	C9—H9A	0.9600
C1—C6	1.384 (2)	C9—H9B	0.9600
C2—C3	1.385 (3)	C9—H9C	0.9600
C3—C4	1.377 (2)	C10—H10A	0.9600
C4—C5	1.387 (3)	C10—H10B	0.9600
C5—C6	1.382 (3)	C10—H10C	0.9600
C6—C7	1.478 (3)

O1—S1—O2	117.54 (9)	C1—C2—H2	122.00
O1—S1—N1	109.42 (8)	C3—C2—H2	122.00
O1—S1—C1	110.06 (9)	C2—C3—H3	119.00
O2—S1—N1	109.04 (8)	C4—C3—H3	119.00
O2—S1—C1	112.19 (9)	C3—C4—H4	119.00
N1—S1—C1	96.54 (8)	C5—C4—H4	119.00
C7—O3—C8	117.70 (14)	C4—C5—H5	121.00
S1—N1—C7	109.19 (13)	C6—C5—H5	121.00
S1—C1—C2	130.80 (12)	O3—C8—H8	110.00
S1—C1—C6	106.85 (13)	C9—C8—H8	110.00
C2—C1—C6	122.32 (17)	C10—C8—H8	110.00
C1—C2—C3	116.66 (15)	C8—C9—H9A	109.00
C2—C3—C4	121.7 (2)	C8—C9—H9B	109.00
C3—C4—C5	121.20 (18)	C8—C9—H9C	109.00
C4—C5—C6	117.64 (15)	H9A—C9—H9B	110.00
C1—C6—C5	120.49 (16)	H9A—C9—H9C	109.00
C1—C6—C7	109.38 (15)	H9B—C9—H9C	110.00
C5—C6—C7	130.13 (14)	C8—C10—H10A	109.00
O3—C7—N1	124.94 (16)	C8—C10—H10B	109.00
O3—C7—C6	117.08 (15)	C8—C10—H10C	109.00
N1—C7—C6	117.98 (14)	H10A—C10—H10B	110.00
O3—C8—C9	105.62 (16)	H10A—C10—H10C	109.00
O3—C8—C10	108.91 (16)	H10B—C10—H10C	110.00
C9—C8—C10	113.00 (16)

O1—S1—N1—C7	−114.21 (14)	C2—C1—C6—C7	−179.48 (15)
O2—S1—N1—C7	115.99 (13)	S1—C1—C6—C5	−176.95 (13)
C1—S1—N1—C7	−0.22 (13)	S1—C1—C2—C3	177.44 (14)
O1—S1—C1—C2	−65.92 (19)	C6—C1—C2—C3	−0.4 (3)
O2—S1—C1—C2	66.96 (19)	S1—C1—C6—C7	2.25 (16)
N1—S1—C1—C2	−179.38 (17)	C2—C1—C6—C5	1.3 (3)
O1—S1—C1—C6	112.15 (13)	C1—C2—C3—C4	−1.0 (3)
O2—S1—C1—C6	−114.97 (13)	C2—C3—C4—C5	1.5 (3)
N1—S1—C1—C6	−1.30 (13)	C3—C4—C5—C6	−0.5 (3)
C8—O3—C7—N1	4.5 (2)	C4—C5—C6—C7	−179.86 (16)
C8—O3—C7—C6	−175.82 (13)	C4—C5—C6—C1	−0.8 (2)
C7—O3—C8—C10	76.34 (18)	C5—C6—C7—N1	176.34 (17)
C7—O3—C8—C9	−162.02 (15)	C1—C6—C7—O3	177.57 (14)
S1—N1—C7—C6	1.72 (19)	C1—C6—C7—N1	−2.8 (2)
S1—N1—C7—O3	−178.64 (13)	C5—C6—C7—O3	−3.3 (3)

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁NO₃S
M_r	225.27
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.1899 (3), 8.8361 (4), 8.9045 (4)
α, β, γ (°)	101.624 (2), 106.694 (1), 114.898 (1)
V (Å³)	519.89 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.13 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9516, 2560, 2090
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.102, 1.05
No. of reflections	2560
No. of parameters	138
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.34

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999), PARST (Nardelli, 1983) and PLATON (Spek, 2009).

Acknowledgements

The authors are grateful to the Higher Education Commission (HEC), Pakistan, for providing funds for the single-crystal XRD facilities at GC University, Lahore.

References

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