4-(5-Oxo-5H-1,2,4-dithia-zol-3-yl)phenyl 4-methyl-benzene-sulfonate.

In the mol-ecular structure of the title compound, C(15)H(11)NO(4)S(3), the 1,2,4-dithia-zolone and central benzene rings are approximately coplanar, making a dihedral angle of 3.08 (7)°. The central benzene ring and the 4-methyl-benzene ring subtend a dihedral angle of 57.47 (8)°. In the crystal, π-π stacking occurs between the central benzene ring and the 1,2,4-dithia-zolone ring of adjacent mol-ecules, which are aligned almost parallel, the centroid-centroid distance being 3.555 (7) Å.

Related literature

For the synthesis of related compounds, see: Cho et al. (2003 ▶); Chen et al. (1996 ▶). For their biological activity, see: Iwakawa et al. (1994 ▶).

Experimental

Crystal data

C15H11NO4S3

M = 365.43

Orthorhombic,

a = 30.2449 (9) Å

b = 7.0841 (3) Å

c = 14.6755 (5) Å

V = 3144.36 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.49 mm−1

T = 145 K

0.25 × 0.20 × 0.20 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.952, T max = 1.000

6725 measured reflections

2775 independent reflections

2355 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.078

S = 1.04

2775 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055607/im2348sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055607/im2348Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055607/im2348Isup3.cml

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

C15H11NO4S3	Dx = 1.544 Mg m−3
Mr = 365.43	Mo Kα radiation, λ = 0.7107 Å
Orthorhombic, Pbcn	Cell parameters from 3356 reflections
a = 30.2449 (9) Å	θ = 2.9–28.8°
b = 7.0841 (3) Å	µ = 0.49 mm−1
c = 14.6755 (5) Å	T = 145 K
V = 3144.36 (18) Å3	Block, colorless
Z = 8	0.25 × 0.20 × 0.20 mm
F(000) = 1504

Agilent Xcalibur Eos diffractometer	2775 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2355 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 16.0874 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −33→35
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −6→8
Tmin = 0.952, Tmax = 1.000	l = −10→17
6725 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0338P)2 + 1.4416P] where P = (Fo2 + 2Fc2)/3
2775 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	−0.163728 (17)	0.52253 (8)	0.56985 (4)	0.03114 (16)
S2	0.060198 (17)	0.13631 (7)	0.67063 (4)	0.02683 (15)
S3	0.094456 (17)	−0.09859 (7)	0.70721 (4)	0.02913 (15)
O1	−0.20211 (5)	0.5638 (2)	0.51776 (12)	0.0445 (4)
O2	−0.13702 (5)	0.6722 (2)	0.60383 (12)	0.0418 (4)
O3	0.05762 (5)	−0.4287 (2)	0.68332 (12)	0.0405 (4)
O4	−0.13468 (5)	0.3962 (2)	0.50138 (10)	0.0308 (4)
N2	0.01393 (5)	−0.1767 (2)	0.63961 (12)	0.0252 (4)
C1	−0.17634 (6)	0.3654 (3)	0.65777 (15)	0.0255 (5)
C2	−0.15800 (7)	0.3921 (3)	0.74340 (16)	0.0312 (5)
H2	−0.1378	0.4924	0.7540	0.037*
C3	−0.16952 (7)	0.2713 (4)	0.81257 (16)	0.0379 (6)
H3	−0.1574	0.2903	0.8716	0.045*
C4	−0.19842 (7)	0.1220 (4)	0.79851 (17)	0.0388 (6)
C5	−0.21578 (7)	0.0968 (3)	0.71170 (18)	0.0402 (6)
H5	−0.2353	−0.0057	0.7007	0.048*
C6	−0.20530 (7)	0.2173 (3)	0.64109 (16)	0.0324 (5)
H6	−0.2177	0.1993	0.5822	0.039*
C7	−0.21083 (9)	−0.0087 (5)	0.8753 (2)	0.0632 (9)
H7A	−0.2430	−0.0261	0.8761	0.095*
H7B	−0.2012	0.0460	0.9333	0.095*
H7C	−0.1964	−0.1311	0.8664	0.095*
C8	−0.09673 (6)	0.3042 (3)	0.53602 (14)	0.0249 (5)
C9	−0.05942 (6)	0.4055 (3)	0.55942 (15)	0.0287 (5)
H9	−0.0588	0.5390	0.5535	0.034*
C10	−0.02302 (7)	0.3088 (3)	0.59164 (15)	0.0275 (5)
H10	0.0028	0.3762	0.6091	0.033*
C11	−0.02389 (6)	0.1121 (3)	0.59875 (13)	0.0218 (4)
C12	−0.06182 (6)	0.0141 (3)	0.57370 (14)	0.0245 (4)
H12	−0.0625	−0.1197	0.5780	0.029*
C13	−0.09845 (7)	0.1102 (3)	0.54266 (14)	0.0264 (5)
H13	−0.1245	0.0437	0.5261	0.032*
C14	0.01431 (6)	0.0060 (3)	0.63420 (13)	0.0224 (4)
C15	0.05148 (7)	−0.2615 (3)	0.67444 (15)	0.0282 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0248 (3)	0.0286 (3)	0.0401 (3)	0.0061 (2)	0.0028 (2)	0.0039 (3)
S2	0.0256 (3)	0.0214 (3)	0.0335 (3)	0.0013 (2)	−0.0051 (2)	−0.0017 (2)
S3	0.0264 (3)	0.0249 (3)	0.0361 (3)	0.0036 (2)	−0.0070 (2)	−0.0011 (2)
O1	0.0302 (8)	0.0534 (11)	0.0498 (11)	0.0164 (8)	−0.0020 (8)	0.0137 (9)
O2	0.0383 (9)	0.0240 (8)	0.0631 (11)	−0.0013 (7)	0.0100 (9)	−0.0006 (8)
O3	0.0388 (9)	0.0220 (8)	0.0607 (11)	0.0036 (7)	−0.0145 (9)	0.0032 (8)
O4	0.0254 (7)	0.0375 (9)	0.0297 (8)	0.0089 (6)	−0.0002 (7)	0.0033 (7)
N2	0.0254 (9)	0.0224 (9)	0.0279 (10)	0.0009 (7)	−0.0009 (8)	0.0009 (8)
C1	0.0181 (10)	0.0261 (11)	0.0322 (11)	0.0028 (8)	0.0013 (9)	−0.0050 (9)
C2	0.0237 (11)	0.0336 (12)	0.0362 (13)	−0.0027 (9)	−0.0021 (10)	−0.0091 (10)
C3	0.0297 (12)	0.0543 (16)	0.0296 (12)	0.0033 (11)	−0.0023 (11)	−0.0029 (11)
C4	0.0259 (12)	0.0476 (15)	0.0428 (14)	0.0008 (10)	0.0059 (11)	0.0102 (12)
C5	0.0270 (12)	0.0368 (13)	0.0566 (16)	−0.0108 (10)	0.0000 (11)	0.0002 (12)
C6	0.0255 (11)	0.0347 (12)	0.0369 (13)	−0.0022 (10)	−0.0040 (10)	−0.0060 (11)
C7	0.0435 (15)	0.081 (2)	0.065 (2)	−0.0094 (15)	0.0105 (15)	0.0295 (17)
C8	0.0214 (10)	0.0319 (12)	0.0215 (10)	0.0066 (9)	0.0007 (9)	0.0013 (9)
C9	0.0280 (11)	0.0229 (11)	0.0350 (12)	0.0024 (9)	0.0036 (10)	0.0027 (10)
C10	0.0221 (10)	0.0275 (11)	0.0329 (12)	−0.0001 (9)	−0.0001 (9)	−0.0009 (10)
C11	0.0230 (10)	0.0237 (11)	0.0186 (10)	0.0030 (8)	0.0034 (8)	−0.0004 (8)
C12	0.0259 (10)	0.0230 (11)	0.0247 (10)	−0.0002 (8)	0.0027 (9)	−0.0016 (9)
C13	0.0238 (10)	0.0289 (12)	0.0266 (11)	−0.0004 (9)	0.0013 (9)	−0.0017 (9)
C14	0.0223 (10)	0.0263 (11)	0.0185 (10)	0.0002 (8)	0.0030 (8)	−0.0025 (9)
C15	0.0293 (11)	0.0252 (12)	0.0300 (11)	0.0001 (9)	−0.0028 (10)	−0.0007 (9)

S1—O1	1.4204 (16)	C4—C7	1.506 (3)
S1—O2	1.4229 (16)	C5—H5	0.9500
S1—O4	1.6069 (15)	C5—C6	1.380 (3)
S1—C1	1.746 (2)	C6—H6	0.9500
S2—S3	2.0325 (7)	C7—H7A	0.9800
S2—C14	1.7506 (19)	C7—H7B	0.9800
S3—C15	1.803 (2)	C7—H7C	0.9800
O3—C15	1.206 (2)	C8—C9	1.381 (3)
O4—C8	1.414 (2)	C8—C13	1.379 (3)
N2—C14	1.297 (2)	C9—H9	0.9500
N2—C15	1.383 (3)	C9—C10	1.380 (3)
C1—C2	1.387 (3)	C10—H10	0.9500
C1—C6	1.388 (3)	C10—C11	1.398 (3)
C2—H2	0.9500	C11—C12	1.390 (3)
C2—C3	1.373 (3)	C11—C14	1.473 (3)
C3—H3	0.9500	C12—H12	0.9500
C3—C4	1.387 (3)	C12—C13	1.378 (3)
C4—C5	1.390 (3)	C13—H13	0.9500
O1—S1—O2	119.95 (10)	C4—C7—H7B	109.5
O1—S1—O4	103.00 (9)	C4—C7—H7C	109.5
O1—S1—C1	110.51 (10)	H7A—C7—H7B	109.5
O2—S1—O4	108.89 (9)	H7A—C7—H7C	109.5
O2—S1—C1	109.88 (10)	H7B—C7—H7C	109.5
O4—S1—C1	103.08 (9)	C9—C8—O4	120.89 (18)
C14—S2—S3	93.04 (7)	C13—C8—O4	116.98 (18)
C15—S3—S2	94.93 (7)	C13—C8—C9	122.11 (19)
C8—O4—S1	118.39 (13)	C8—C9—H9	120.7
C14—N2—C15	116.67 (17)	C10—C9—C8	118.61 (19)
C2—C1—S1	119.67 (16)	C10—C9—H9	120.7
C2—C1—C6	121.0 (2)	C9—C10—H10	119.8
C6—C1—S1	119.29 (17)	C9—C10—C11	120.38 (19)
C1—C2—H2	120.6	C11—C10—H10	119.8
C3—C2—C1	118.9 (2)	C10—C11—C14	121.35 (18)
C3—C2—H2	120.6	C12—C11—C10	119.56 (18)
C2—C3—H3	119.2	C12—C11—C14	119.07 (17)
C2—C3—C4	121.7 (2)	C11—C12—H12	119.9
C4—C3—H3	119.2	C13—C12—C11	120.30 (19)
C3—C4—C5	118.2 (2)	C13—C12—H12	119.9
C3—C4—C7	121.0 (2)	C8—C13—H13	120.5
C5—C4—C7	120.9 (2)	C12—C13—C8	119.03 (19)
C4—C5—H5	119.3	C12—C13—H13	120.5
C6—C5—C4	121.5 (2)	N2—C14—S2	120.98 (15)
C6—C5—H5	119.3	N2—C14—C11	121.59 (17)
C1—C6—H6	120.7	C11—C14—S2	117.42 (14)
C5—C6—C1	118.7 (2)	O3—C15—S3	119.25 (16)
C5—C6—H6	120.7	O3—C15—N2	126.36 (19)
C4—C7—H7A	109.5	N2—C15—S3	114.38 (15)