Crystal structure of (E)-3-allyl-2-sulfanyl-idene-5-[(thio-phen-2-yl)methyl-idene]thia-zolidin-4-one.

Mol-ecules of the title compound, C11H9NOS3, are built up by one thio-phene and one 2-thioxa-thia-zolidin-4-one ring which are connected by a methyl-ene bridge. In addition, there is an allyl substituent attached to nitro-gen. The two rings are almost coplanar, making a dihedral angle between them of 0.76 (11)°. The allyl group is oriented perpendicular to the mean plane through both ring systems. The crystal structure exhibits inversion dimers in which mol-ecules are linked by pairs of C-H⋯O hydrogen bonds. Additional π-π inter-actions between neighboring thio-phene and 2-thioxa-thia-zolidin-4-one rings [inter-centroid distance = 3.694 (2) Å] lead to the formation of a three-dimensional network.

Related literature

For pharmacological activities such as anti­microbial and anti-inflammatory of aryl­idene derivatives of rhodanine (2-thioxo-1,3-thia­zolidin-4-one), see: Soltero-Higgin et al. (2004 ▸); Hu et al. (2004 ▸); Nasr & Said (2003 ▸); Johnson et al. (2001 ▸); Sortino et al. (2007 ▸); Insuasty et al. (2010 ▸); Tomasic & Masic (2009 ▸).

Experimental

Crystal data

C11H9NOS3

M = 267.37

Triclinic,

a = 6.7342 (2) Å

b = 7.3762 (2) Å

c = 13.2917 (5) Å

α = 79.386 (2)°

β = 80.104 (2)°

γ = 68.908 (1)°

V = 601.44 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.59 mm−1

T = 296 K

0.37 × 0.35 × 0.28 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.700, T max = 0.746

25223 measured reflections

3514 independent reflections

2557 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.07

3514 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▸) and ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015010166/im2466sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015010166/im2466Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015010166/im2466Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015010166/im2466fig1.tif

Mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles of arbitrary radius.

Click here for additional data file.

. DOI: 10.1107/S2056989015010166/im2466fig2.tif

Partial crystal packing of the title compound showing hydrogen bonds and π–π inter­actions between mol­ecules.

CCDC reference: 1403058

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H9NOS3	Z = 2
Mr = 267.37	F(000) = 276
Triclinic, P1	Dx = 1.476 Mg m−3
a = 6.7342 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.3762 (2) Å	Cell parameters from 3514 reflections
c = 13.2917 (5) Å	θ = 3.0–30.0°
α = 79.386 (2)°	µ = 0.59 mm−1
β = 80.104 (2)°	T = 296 K
γ = 68.908 (1)°	Block, yellow
V = 601.44 (3) Å3	0.37 × 0.35 × 0.28 mm

Bruker X8 APEX diffractometer	3514 independent reflections
Radiation source: fine-focus sealed tube	2557 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 30.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.700, Tmax = 0.746	k = −10→10
25223 measured reflections	l = −18→18

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0384P)2 + 0.3716P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3514 reflections	Δρmax = 0.35 e Å−3
145 parameters	Δρmin = −0.26 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.

	x	y	z	Uiso*/Ueq
C1	0.1345 (4)	0.1860 (4)	0.70306 (19)	0.0518 (6)
H1	−0.0046	0.2033	0.7342	0.062*
C2	0.3105 (4)	0.0861 (4)	0.75114 (18)	0.0523 (6)
H2	0.3058	0.0267	0.8192	0.063*
C3	0.5018 (4)	0.0808 (3)	0.68783 (17)	0.0428 (5)
H3	0.6372	0.0182	0.7094	0.051*
C4	0.4669 (3)	0.1785 (3)	0.59025 (16)	0.0350 (4)
C5	0.6327 (3)	0.1940 (3)	0.50925 (16)	0.0358 (4)
H5	0.7718	0.1321	0.5264	0.043*
C6	0.6167 (3)	0.2849 (3)	0.41203 (16)	0.0341 (4)
C7	0.8086 (3)	0.2828 (3)	0.33909 (16)	0.0366 (4)
C8	0.5339 (3)	0.4692 (3)	0.23605 (17)	0.0399 (5)
C9	0.9117 (4)	0.4146 (4)	0.15934 (19)	0.0491 (6)
H9A	0.8550	0.5408	0.1181	0.059*
H9B	1.0355	0.4141	0.1876	0.059*
C10	0.9801 (6)	0.2599 (5)	0.0927 (2)	0.0743 (9)
H10	0.8740	0.2392	0.0646	0.089*
C11	1.1737 (7)	0.1513 (6)	0.0701 (3)	0.1111 (16)
H11A	1.2845	0.1674	0.0967	0.133*
H11B	1.2038	0.0562	0.0272	0.133*
N1	0.7483 (3)	0.3913 (3)	0.24437 (13)	0.0382 (4)
O1	0.9933 (2)	0.2023 (3)	0.35541 (13)	0.0515 (4)
S1	0.19548 (9)	0.27676 (9)	0.57905 (5)	0.04606 (16)
S2	0.38596 (8)	0.41472 (8)	0.35129 (4)	0.03895 (14)
S3	0.41977 (12)	0.59688 (12)	0.13403 (5)	0.0646 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0437 (13)	0.0519 (14)	0.0552 (15)	−0.0171 (11)	0.0135 (11)	−0.0117 (11)
C2	0.0583 (15)	0.0566 (14)	0.0374 (12)	−0.0213 (12)	0.0061 (11)	−0.0020 (10)
C3	0.0425 (12)	0.0437 (12)	0.0389 (11)	−0.0123 (10)	−0.0042 (9)	−0.0028 (9)
C4	0.0343 (10)	0.0315 (10)	0.0392 (11)	−0.0108 (8)	−0.0029 (8)	−0.0065 (8)
C5	0.0316 (10)	0.0343 (10)	0.0406 (11)	−0.0101 (8)	−0.0032 (8)	−0.0054 (8)
C6	0.0304 (9)	0.0340 (10)	0.0377 (10)	−0.0111 (8)	−0.0022 (8)	−0.0060 (8)
C7	0.0337 (10)	0.0393 (11)	0.0389 (11)	−0.0156 (9)	−0.0002 (8)	−0.0077 (9)
C8	0.0402 (11)	0.0412 (11)	0.0394 (11)	−0.0151 (9)	−0.0030 (9)	−0.0063 (9)
C9	0.0447 (13)	0.0555 (14)	0.0469 (13)	−0.0242 (11)	0.0066 (10)	−0.0024 (10)
C10	0.084 (2)	0.086 (2)	0.0568 (17)	−0.0438 (19)	0.0266 (15)	−0.0216 (15)
C11	0.133 (4)	0.086 (3)	0.067 (2)	0.002 (2)	0.025 (2)	−0.0083 (19)
N1	0.0360 (9)	0.0424 (9)	0.0370 (9)	−0.0165 (8)	0.0006 (7)	−0.0051 (7)
O1	0.0298 (8)	0.0662 (11)	0.0532 (10)	−0.0130 (7)	−0.0035 (7)	−0.0032 (8)
S1	0.0340 (3)	0.0453 (3)	0.0515 (3)	−0.0083 (2)	−0.0008 (2)	−0.0031 (2)
S2	0.0291 (2)	0.0432 (3)	0.0410 (3)	−0.0101 (2)	−0.0029 (2)	−0.0024 (2)
S3	0.0557 (4)	0.0842 (5)	0.0448 (4)	−0.0184 (4)	−0.0133 (3)	0.0101 (3)

C1—C2	1.347 (4)	C7—O1	1.208 (2)
C1—S1	1.701 (3)	C7—N1	1.400 (3)
C1—H1	0.9300	C8—N1	1.364 (3)
C2—C3	1.405 (3)	C8—S3	1.638 (2)
C2—H2	0.9300	C8—S2	1.743 (2)
C3—C4	1.377 (3)	C9—C10	1.468 (4)
C3—H3	0.9300	C9—N1	1.468 (3)
C4—C5	1.433 (3)	C9—H9A	0.9700
C4—S1	1.729 (2)	C9—H9B	0.9700
C5—C6	1.344 (3)	C10—C11	1.278 (5)
C5—H5	0.9300	C10—H10	0.9300
C6—C7	1.473 (3)	C11—H11A	0.9300
C6—S2	1.749 (2)	C11—H11B	0.9300
C2—C1—S1	112.36 (18)	N1—C8—S3	126.87 (17)
C2—C1—H1	123.8	N1—C8—S2	110.96 (16)
S1—C1—H1	123.8	S3—C8—S2	122.17 (13)
C1—C2—C3	113.0 (2)	C10—C9—N1	113.0 (2)
C1—C2—H2	123.5	C10—C9—H9A	109.0
C3—C2—H2	123.5	N1—C9—H9A	109.0
C4—C3—C2	112.6 (2)	C10—C9—H9B	109.0
C4—C3—H3	123.7	N1—C9—H9B	109.0
C2—C3—H3	123.7	H9A—C9—H9B	107.8
C3—C4—C5	124.61 (19)	C11—C10—C9	125.3 (4)
C3—C4—S1	110.43 (16)	C11—C10—H10	117.4
C5—C4—S1	124.96 (16)	C9—C10—H10	117.4
C6—C5—C4	129.47 (19)	C10—C11—H11A	120.0
C6—C5—H5	115.3	C10—C11—H11B	120.0
C4—C5—H5	115.3	H11A—C11—H11B	120.0
C5—C6—C7	121.35 (19)	C8—N1—C7	116.63 (17)
C5—C6—S2	128.78 (16)	C8—N1—C9	122.99 (19)
C7—C6—S2	109.86 (15)	C7—N1—C9	120.37 (18)
O1—C7—N1	123.06 (19)	C1—S1—C4	91.64 (11)
O1—C7—C6	126.9 (2)	C8—S2—C6	92.49 (10)
N1—C7—C6	110.02 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.93	2.54	3.304 (3)	140

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C3H3O1i	0.93	2.54	3.304(3)	140

Symmetry code: (i) .