2-[(E)-3-Phenyl­prop-2-en­yl]-1,2-benzisothia­zol-3(2H)-one 1,1-dioxide

Arshad, M.N.; Mubashar-ur-Rehman, H.; Zia-ur-Rehman, M.; Khan, I.U.; Shafique, M.

doi:10.1107/S1600536809012999

2-[(E)-3-Phenylprop-2-enyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

M. N. Arshad, H. Mubashar-ur-Rehman, M. Zia-ur-Rehman, I. U. Khan and M. Shafique

In the crystal structure of the title compound, C₁₆H₁₃NO₃S, the benzisothiazole group is almost planar (r.m.s. deviation for all non-H atoms excluding the two O atoms bonded to S = 0.009 Å). The dihedral angle between the fused ring and the terminal ring is 13.8 (1)°. In the crystal, molecules are linked through intermolecular C—H

O contacts forming a chain of molecules along b.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809012999/bt2924sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809012999/bt2924Isup2.hkl Contains datablock I

CCDC reference: 731251

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R factor = 0.051
wR factor = 0.178
Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   296.000
            Value of melting point given =     0.000
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    --  C11     ..       6.51 su
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

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

   0 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
   1 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

Benzisothiazolone-1,1-dioxide and its various derivatives are well known as biologically active compounds e.g., saccharin has been identified as an important molecular component in various classes of 5-HTla antagonists, analgesics and human mast cell tryptase inhibitors (Liang et al., 2006). Few of its derivatives are considered to be the most potent orally active human leucocyte elastase (HLE) inhibitors for the treatment ofchronic obstructive pulmonary disease (COPD), acute respiratory distress syndrome (ARDS), cystic fibrosis, asthma and other inflammatory diseases (Kapui et al., 2003). Its N-alkyl derivatives have been successfully transformed to non-steroidal anti-inflammatory drugs e.g., piroxicam (Zia-ur-Rehman et al., 2006).

In continuation to our research on the synthesis of 1,2-benzothiazine 1,1-dioxide derivatives (Zia-ur-Rehman et al., 2009; Zia-ur-Rehman et al., 2006), we have in addtion, worked on the synthesis of benzisothiazole derivatives (Siddiqui et al., 2006; Siddiqui et al., 2008). Herein, crystal structure of the title compound (I) is described. The benzisothiazole moiety is exactly planar.The molecular dimensions are in accord with the corresponding dimensions reported in similar structures (Siddiqui et al., 2007a-c). Each molecule is linked to its adjacent one through C—H···O contacts forming a chain of molecules along b.

Related literature top

For the synthesis of benzothiazine and benzisothiazol derivatives, see: Zia-ur-Rehman et al. (2006, 2009); Siddiqui et al. (2008). For the biological activity of benzisothiazols, see: Kapui et al. (2003); Liang et al. (2006). For related structures, see: Siddiqui et al. (2006, 2007a,b,c).

Experimental top

A mixture of 2,3-dihydro-1,2-benzisothiazol-3-one-1,1-dioxide (1.83 g, 10.0 mmoles), dimethyl formamide (5.0 ml) and cinnamyl chloride (1.67 g, 10.0 mmoles) was stirred for a period of three hours at 90°C. Contents were cooled to room temperature; poured over crushed ice to get white coloured precipitates which were filtered, washed and dried. Crystallization of the white precipitates (in methanol) afforded suitable crystals for X-ray studies after recrystalization in methanol.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SMART (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: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Perspective view of the crystal packing showing inter molecular C—H···O interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

2-[(E)-3-Phenylprop-2-enyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide top

Crystal data top

C₁₆H₁₃NO₃S	F(000) = 624
M_r = 299.33	D_x = 1.357 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1453 reflections
a = 6.9375 (5) Å	θ = 2.8–20.7°
b = 7.1579 (4) Å	µ = 0.23 mm⁻¹
c = 29.673 (2) Å	T = 296 K
β = 96.160 (4)°	Needles, white
V = 1464.99 (17) Å³	0.39 × 0.11 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	1722 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 28.3°, θ_min = 1.4°
ϕ and ω scans	h = −9→8
8250 measured reflections	k = −8→9
3606 independent reflections	l = −35→39

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.178	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0875P)²] where P = (F_o² + 2F_c²)/3
3606 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₆H₁₃NO₃S	V = 1464.99 (17) Å³
M_r = 299.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.9375 (5) Å	µ = 0.23 mm⁻¹
b = 7.1579 (4) Å	T = 296 K
c = 29.673 (2) Å	0.39 × 0.11 × 0.10 mm
β = 96.160 (4)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1722 reflections with I > 2σ(I)
8250 measured reflections	R_int = 0.034
3606 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 0.96	Δρ_max = 0.32 e Å⁻³
3606 reflections	Δρ_min = −0.40 e Å⁻³
190 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.

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.

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

	x	y	z	U_iso*/U_eq
S1	0.25184 (11)	−0.21860 (10)	0.08353 (3)	0.0673 (3)
O1	0.2457 (3)	0.2827 (3)	0.05026 (8)	0.0871 (7)
O2	0.4314 (3)	−0.2892 (3)	0.10446 (8)	0.0937 (8)
O3	0.0787 (3)	−0.2970 (3)	0.09666 (7)	0.0909 (7)
N1	0.2464 (3)	0.0118 (3)	0.09024 (7)	0.0634 (6)
C1	0.2500 (4)	−0.1992 (4)	0.02512 (9)	0.0552 (7)
C2	0.2505 (4)	−0.3412 (4)	−0.00625 (12)	0.0800 (9)
H2	0.2512	−0.4661	0.0025	0.096*
C3	0.2499 (5)	−0.2902 (6)	−0.05133 (12)	0.0914 (11)
H3	0.2495	−0.3827	−0.0733	0.110*
C4	0.2498 (4)	−0.1074 (6)	−0.06412 (11)	0.0805 (9)
H4	0.2496	−0.0775	−0.0946	0.097*
C5	0.2501 (4)	0.0333 (5)	−0.03269 (10)	0.0654 (8)
H5	0.2500	0.1578	−0.0416	0.078*
C6	0.2506 (3)	−0.0140 (4)	0.01241 (8)	0.0532 (6)
C7	0.2488 (4)	0.1141 (4)	0.05129 (10)	0.0609 (7)
C8	0.2380 (4)	0.0994 (5)	0.13459 (10)	0.0799 (9)
H8A	0.1591	0.0230	0.1524	0.096*
H8B	0.1762	0.2206	0.1304	0.096*
C9	0.4368 (4)	0.1238 (5)	0.16027 (10)	0.0735 (8)
H9	0.4949	0.0193	0.1746	0.088*
C10	0.5312 (5)	0.2786 (4)	0.16377 (9)	0.0700 (8)
H10	0.4704	0.3826	0.1499	0.084*
C11	0.7266 (4)	0.3074 (4)	0.18770 (9)	0.0603 (7)
C12	0.8373 (5)	0.4574 (4)	0.17645 (9)	0.0768 (9)
H12	0.7871	0.5416	0.1544	0.092*
C13	1.0228 (5)	0.4829 (5)	0.19796 (11)	0.0834 (10)
H13	1.0982	0.5821	0.1897	0.100*
C14	1.0949 (5)	0.3626 (5)	0.23127 (12)	0.0838 (10)
H14	1.2193	0.3801	0.2457	0.101*
C15	0.9854 (5)	0.2174 (5)	0.24335 (11)	0.0799 (9)
H15	1.0337	0.1375	0.2666	0.096*
C16	0.8052 (5)	0.1884 (4)	0.22158 (10)	0.0745 (9)
H16	0.7332	0.0865	0.2296	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0771 (6)	0.0647 (5)	0.0584 (5)	0.0005 (4)	−0.0004 (4)	0.0158 (4)
O1	0.1019 (17)	0.0544 (13)	0.1044 (19)	0.0035 (11)	0.0083 (13)	0.0060 (11)
O2	0.1041 (17)	0.0869 (15)	0.0828 (16)	0.0187 (12)	−0.0234 (13)	0.0209 (12)
O3	0.1006 (17)	0.0970 (17)	0.0785 (16)	−0.0211 (12)	0.0253 (13)	0.0253 (12)
N1	0.0710 (15)	0.0670 (15)	0.0509 (14)	0.0007 (11)	0.0009 (11)	0.0008 (11)
C1	0.0510 (15)	0.0568 (16)	0.0570 (16)	−0.0012 (11)	0.0015 (13)	0.0099 (13)
C2	0.098 (2)	0.0619 (19)	0.080 (2)	−0.0007 (16)	0.0071 (19)	−0.0011 (17)
C3	0.104 (3)	0.107 (3)	0.064 (2)	0.004 (2)	0.013 (2)	−0.014 (2)
C4	0.067 (2)	0.113 (3)	0.062 (2)	0.0019 (18)	0.0115 (16)	0.012 (2)
C5	0.0494 (16)	0.081 (2)	0.0669 (19)	0.0027 (14)	0.0093 (14)	0.0217 (17)
C6	0.0398 (14)	0.0625 (17)	0.0572 (16)	0.0007 (11)	0.0043 (12)	0.0131 (13)
C7	0.0500 (16)	0.0592 (19)	0.073 (2)	0.0009 (12)	0.0023 (14)	0.0112 (15)
C8	0.072 (2)	0.100 (2)	0.068 (2)	−0.0014 (17)	0.0060 (16)	−0.0131 (17)
C9	0.082 (2)	0.079 (2)	0.0603 (19)	0.0036 (17)	0.0112 (16)	0.0005 (15)
C10	0.084 (2)	0.074 (2)	0.0532 (18)	0.0113 (17)	0.0096 (16)	0.0003 (14)
C11	0.0657 (18)	0.0722 (19)	0.0438 (15)	0.0036 (14)	0.0103 (14)	−0.0014 (13)
C12	0.106 (3)	0.076 (2)	0.0497 (17)	−0.0063 (18)	0.0141 (17)	0.0012 (15)
C13	0.100 (3)	0.089 (2)	0.065 (2)	−0.0285 (19)	0.0236 (19)	−0.0086 (18)
C14	0.067 (2)	0.115 (3)	0.069 (2)	−0.0069 (19)	0.0076 (17)	−0.012 (2)
C15	0.073 (2)	0.095 (2)	0.070 (2)	0.0056 (18)	0.0020 (18)	0.0096 (18)
C16	0.073 (2)	0.078 (2)	0.072 (2)	−0.0025 (15)	0.0068 (17)	0.0110 (16)

Geometric parameters (Å, º) top

S1—O3	1.418 (2)	C8—C9	1.512 (4)
S1—O2	1.424 (2)	C8—H8A	0.9700
S1—N1	1.662 (2)	C8—H8B	0.9700
S1—C1	1.738 (3)	C9—C10	1.286 (4)
O1—C7	1.207 (3)	C9—H9	0.9300
N1—C7	1.370 (3)	C10—C11	1.476 (4)
N1—C8	1.464 (3)	C10—H10	0.9300
C1—C6	1.378 (3)	C11—C12	1.382 (4)
C1—C2	1.378 (4)	C11—C16	1.384 (4)
C2—C3	1.387 (4)	C12—C13	1.386 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.362 (5)	C13—C14	1.365 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.372 (4)	C14—C15	1.358 (4)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.380 (3)	C15—C16	1.360 (4)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.475 (4)	C16—H16	0.9300

O3—S1—O2	117.84 (14)	N1—C8—C9	112.4 (2)
O3—S1—N1	109.21 (13)	N1—C8—H8A	109.1
O2—S1—N1	109.29 (12)	C9—C8—H8A	109.1
O3—S1—C1	112.95 (13)	N1—C8—H8B	109.1
O2—S1—C1	112.08 (14)	C9—C8—H8B	109.1
N1—S1—C1	92.43 (12)	H8A—C8—H8B	107.9
C7—N1—C8	122.3 (3)	C10—C9—C8	124.7 (3)
C7—N1—S1	115.28 (19)	C10—C9—H9	117.7
C8—N1—S1	122.4 (2)	C8—C9—H9	117.7
C6—C1—C2	121.6 (3)	C9—C10—C11	126.3 (3)
C6—C1—S1	110.5 (2)	C9—C10—H10	116.8
C2—C1—S1	127.9 (2)	C11—C10—H10	116.8
C1—C2—C3	117.2 (3)	C12—C11—C16	117.9 (3)
C1—C2—H2	121.4	C12—C11—C10	119.8 (3)
C3—C2—H2	121.4	C16—C11—C10	122.3 (3)
C4—C3—C2	121.5 (3)	C11—C12—C13	120.3 (3)
C4—C3—H3	119.3	C11—C12—H12	119.9
C2—C3—H3	119.3	C13—C12—H12	119.9
C3—C4—C5	121.0 (3)	C14—C13—C12	120.0 (3)
C3—C4—H4	119.5	C14—C13—H13	120.0
C5—C4—H4	119.5	C12—C13—H13	120.0
C4—C5—C6	118.6 (3)	C15—C14—C13	120.1 (3)
C4—C5—H5	120.7	C15—C14—H14	119.9
C6—C5—H5	120.7	C13—C14—H14	119.9
C1—C6—C5	120.1 (3)	C14—C15—C16	120.2 (3)
C1—C6—C7	112.6 (2)	C14—C15—H15	119.9
C5—C6—C7	127.3 (3)	C16—C15—H15	119.9
O1—C7—N1	123.6 (3)	C15—C16—C11	121.5 (3)
O1—C7—C6	127.1 (3)	C15—C16—H16	119.3
N1—C7—C6	109.2 (2)	C11—C16—H16	119.3

O3—S1—N1—C7	−117.2 (2)	C8—N1—C7—O1	0.6 (4)
O2—S1—N1—C7	112.6 (2)	S1—N1—C7—O1	−179.9 (2)
C1—S1—N1—C7	−1.9 (2)	C8—N1—C7—C6	−178.0 (2)
O3—S1—N1—C8	62.3 (2)	S1—N1—C7—C6	1.5 (3)
O2—S1—N1—C8	−67.9 (2)	C1—C6—C7—O1	−178.7 (3)
C1—S1—N1—C8	177.7 (2)	C5—C6—C7—O1	0.4 (4)
O3—S1—C1—C6	113.7 (2)	C1—C6—C7—N1	−0.2 (3)
O2—S1—C1—C6	−110.3 (2)	C5—C6—C7—N1	178.9 (2)
N1—S1—C1—C6	1.6 (2)	C7—N1—C8—C9	−94.9 (3)
O3—S1—C1—C2	−67.1 (3)	S1—N1—C8—C9	85.6 (3)
O2—S1—C1—C2	68.9 (3)	N1—C8—C9—C10	101.9 (4)
N1—S1—C1—C2	−179.2 (3)	C8—C9—C10—C11	−178.7 (3)
C6—C1—C2—C3	−0.5 (4)	C9—C10—C11—C12	157.8 (3)
S1—C1—C2—C3	−179.6 (2)	C9—C10—C11—C16	−22.3 (5)
C1—C2—C3—C4	0.3 (5)	C16—C11—C12—C13	1.6 (4)
C2—C3—C4—C5	−0.1 (5)	C10—C11—C12—C13	−178.4 (3)
C3—C4—C5—C6	0.0 (4)	C11—C12—C13—C14	−1.8 (5)
C2—C1—C6—C5	0.5 (4)	C12—C13—C14—C15	0.1 (5)
S1—C1—C6—C5	179.73 (19)	C13—C14—C15—C16	1.6 (5)
C2—C1—C6—C7	179.7 (2)	C14—C15—C16—C11	−1.8 (5)
S1—C1—C6—C7	−1.1 (3)	C12—C11—C16—C15	0.1 (4)
C4—C5—C6—C1	−0.2 (4)	C10—C11—C16—C15	−179.8 (3)
C4—C5—C6—C7	−179.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.29	3.174 (4)	158

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃NO₃S
M_r	299.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	6.9375 (5), 7.1579 (4), 29.673 (2)
β (°)	96.160 (4)
V (Å³)	1464.99 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.39 × 0.11 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8250, 3606, 1722
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.178, 0.96
No. of reflections	3606
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.40

Computer programs: APEX2 (Bruker, 2007), SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008) and local programs.