2-[(E)-3-Phenyl-prop-2-en-yl]-1,2-benzisothia-zol-3(2H)-one 1,1-dioxide.

In the crystal structure of the title compound, C(16)H(13)NO(3)S, the benzisothia-zole 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, mol-ecules are linked through inter-molecular C-H⋯O contacts forming a chain of mol-ecules along b.

Related literature

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

Crystal data

C16H13NO3S

M = 299.33

Monoclinic,

a = 6.9375 (5) Å

b = 7.1579 (4) Å

c = 29.673 (2) Å

β = 96.160 (4)°

V = 1464.99 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.39 × 0.11 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: none

8250 measured reflections

3606 independent reflections

1722 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.178

S = 0.96

3606 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.40 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809012999/bt2924sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012999/bt2924Isup2.hkl

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

C16H13NO3S	F(000) = 624
Mr = 299.33	Dx = 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

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

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(Fo2) + (0.0875P)2] where P = (Fo2 + 2Fc2)/3
3606 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) .