Crystal structure of (Z)-3-allyl-5-(4-methyl-benzyl-idene)-2-sulfanyl-idene-1,3-thia-zolidin-4-one.

In the title compound, C14H13NOS2, the atoms of the allyl group are disordered over two sets of sites, with an occupancy ratio of 0.559 (10):0.441 (10). The rhodanine ring makes a dihedral angle of 5.51 (12)° with the mean plane through the p-tolyl group. There are no specific inter-molecular inter-actions in the crystal packing.

Related literature

For biological activities of rhodanine-based mol­ecules, see: Tomasić & Masic (2009 ▸); Jiang et al. (2011 ▸); Bulic et al. (2009 ▸); Sing et al. (2001 ▸); Grant et al. (2000 ▸); Orchard et al. (2004 ▸); Cutshall et al. (2005 ▸); Sortino et al. (2007 ▸); Kesel (2003 ▸).

Experimental

Crystal data

C14H13NOS2

M = 275.37

Triclinic,

a = 7.3606 (4) Å

b = 8.8342 (6) Å

c = 11.3134 (7) Å

α = 109.736 (2)°

β = 95.380 (2)°

γ = 96.502 (2)°

V = 681.10 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.38 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

21519 measured reflections

2853 independent reflections

2241 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.133

S = 1.07

2853 reflections

182 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.21 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/S2056989015020460/im2472sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015020460/im2472Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015020460/im2472Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015020460/im2472fig1.tif

Plot of the mol­ecule of the title compound with displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

CCDC reference: 1433844

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

C14H13NOS2	F(000) = 288
Mr = 275.37	Dx = 1.343 Mg m−3
Triclinic, P1	Melting point: 390 K
a = 7.3606 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8342 (6) Å	Cell parameters from 2853 reflections
c = 11.3134 (7) Å	θ = 2.5–26.6°
α = 109.736 (2)°	µ = 0.38 mm−1
β = 95.380 (2)°	T = 296 K
γ = 96.502 (2)°	Block, yellow
V = 681.10 (7) Å3	0.37 × 0.35 × 0.28 mm
Z = 2

Bruker X8 APEX diffractometer	2853 independent reflections
Radiation source: fine-focus sealed tube	2241 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 26.6°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.700, Tmax = 0.746	k = −11→11
21519 measured reflections	l = −14→14

Refinement on F2	2 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.0651P)2 + 0.2196P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2853 reflections	Δρmax = 0.34 e Å−3
182 parameters	Δρmin = −0.21 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	Occ. (<1)
C1	0.5130 (4)	0.6507 (3)	1.2642 (3)	0.0784 (7)
H1A	0.3857	0.6024	1.2376	0.118*
H1B	0.5440	0.6723	1.3533	0.118*
H1C	0.5329	0.7509	1.2481	0.118*
C2	0.6328 (3)	0.5359 (3)	1.1916 (2)	0.0591 (5)
C3	0.8224 (3)	0.5758 (3)	1.2117 (2)	0.0644 (6)
H3	0.8773	0.6754	1.2720	0.077*
C4	0.9323 (3)	0.4717 (3)	1.1444 (2)	0.0608 (6)
H4	1.0599	0.5021	1.1607	0.073*
C5	0.8563 (3)	0.3212 (2)	1.05205 (18)	0.0507 (5)
C6	0.6656 (3)	0.2794 (3)	1.0338 (2)	0.0604 (5)
H6	0.6103	0.1791	0.9747	0.073*
C7	0.5571 (3)	0.3847 (3)	1.1022 (2)	0.0659 (6)
H7	0.4296	0.3536	1.0882	0.079*
C8	0.9804 (3)	0.2217 (3)	0.98157 (19)	0.0530 (5)
H8	1.1048	0.2647	1.0078	0.064*
C9	0.9485 (3)	0.0782 (3)	0.88491 (19)	0.0518 (5)
C10	1.1041 (3)	0.0018 (3)	0.8283 (2)	0.0552 (5)
C11	0.8509 (3)	−0.1882 (3)	0.7007 (2)	0.0594 (5)
C12	1.1670 (4)	−0.2379 (3)	0.6539 (2)	0.0695 (6)
H12A	1.1258	−0.3537	0.6306	0.083*
H12B	1.2900	−0.2102	0.7018	0.083*
C13A	1.1640 (13)	−0.1898 (15)	0.5393 (11)	0.090 (3)	0.441 (10)
H13A	1.0526	−0.2181	0.4852	0.108*	0.441 (10)
C14A	1.3042 (16)	−0.1105 (14)	0.5064 (12)	0.147 (5)	0.441 (10)
H14A	1.4185	−0.0794	0.5573	0.177*	0.441 (10)
H14B	1.2876	−0.0863	0.4326	0.177*	0.441 (10)
C13B	1.2460 (12)	−0.1897 (10)	0.5554 (8)	0.077 (2)	0.559 (10)
H13B	1.3415	−0.2408	0.5196	0.092*	0.559 (10)
C14B	1.1877 (12)	−0.0760 (8)	0.5147 (6)	0.101 (3)	0.559 (10)
H14C	1.0923	−0.0231	0.5491	0.121*	0.559 (10)
H14D	1.2423	−0.0497	0.4519	0.121*	0.559 (10)
N1	1.0378 (3)	−0.1426 (2)	0.72653 (17)	0.0560 (4)
O1	1.2661 (2)	0.0540 (2)	0.86169 (17)	0.0734 (5)
S1	0.73489 (11)	−0.35069 (9)	0.59005 (7)	0.0874 (3)
S2	0.73980 (7)	−0.04619 (7)	0.80585 (5)	0.0607 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0840 (18)	0.0719 (16)	0.0752 (17)	0.0164 (14)	0.0191 (14)	0.0170 (14)
C2	0.0674 (13)	0.0592 (13)	0.0517 (12)	0.0074 (10)	0.0086 (10)	0.0217 (10)
C3	0.0730 (15)	0.0523 (12)	0.0566 (12)	−0.0057 (11)	0.0068 (11)	0.0102 (10)
C4	0.0523 (11)	0.0603 (13)	0.0602 (13)	−0.0082 (10)	0.0000 (10)	0.0165 (11)
C5	0.0541 (11)	0.0526 (11)	0.0445 (10)	−0.0004 (9)	0.0024 (8)	0.0200 (9)
C6	0.0567 (12)	0.0552 (12)	0.0564 (12)	−0.0027 (10)	−0.0022 (10)	0.0093 (10)
C7	0.0497 (12)	0.0697 (14)	0.0679 (14)	0.0011 (10)	0.0030 (10)	0.0149 (12)
C8	0.0503 (11)	0.0537 (11)	0.0523 (11)	−0.0027 (9)	0.0008 (9)	0.0201 (9)
C9	0.0527 (11)	0.0529 (11)	0.0502 (11)	0.0019 (9)	0.0022 (9)	0.0218 (9)
C10	0.0592 (12)	0.0566 (12)	0.0521 (11)	0.0056 (10)	0.0077 (9)	0.0231 (10)
C11	0.0710 (14)	0.0527 (12)	0.0531 (12)	0.0057 (10)	−0.0007 (10)	0.0204 (10)
C12	0.0810 (16)	0.0628 (14)	0.0660 (14)	0.0176 (12)	0.0197 (12)	0.0197 (12)
C13A	0.078 (6)	0.123 (8)	0.077 (5)	0.049 (7)	0.023 (5)	0.030 (5)
C14A	0.171 (11)	0.176 (11)	0.163 (10)	0.100 (10)	0.091 (9)	0.106 (9)
C13B	0.064 (4)	0.102 (4)	0.081 (4)	0.033 (4)	0.036 (4)	0.040 (3)
C14B	0.128 (7)	0.105 (5)	0.092 (4)	0.026 (4)	0.043 (4)	0.054 (4)
N1	0.0635 (11)	0.0541 (10)	0.0526 (10)	0.0100 (8)	0.0082 (8)	0.0211 (8)
O1	0.0546 (9)	0.0745 (11)	0.0810 (11)	0.0037 (8)	0.0101 (8)	0.0164 (9)
S1	0.0934 (5)	0.0627 (4)	0.0795 (5)	0.0007 (3)	−0.0076 (4)	−0.0002 (3)
S2	0.0540 (3)	0.0597 (4)	0.0580 (3)	0.0004 (2)	−0.0020 (2)	0.0126 (3)

C1—C2	1.502 (3)	C10—O1	1.204 (3)
C1—H1A	0.9600	C10—N1	1.397 (3)
C1—H1B	0.9600	C11—N1	1.364 (3)
C1—H1C	0.9600	C11—S1	1.633 (2)
C2—C3	1.378 (3)	C11—S2	1.751 (2)
C2—C7	1.390 (3)	C12—C13B	1.465 (8)
C3—C4	1.374 (3)	C12—N1	1.466 (3)
C3—H3	0.9300	C12—C13A	1.493 (12)
C4—C5	1.399 (3)	C12—H12A	0.9700
C4—H4	0.9300	C12—H12B	0.9700
C5—C6	1.388 (3)	C13A—C14A	1.3337 (10)
C5—C8	1.445 (3)	C13A—H13A	0.9300
C6—C7	1.378 (3)	C14A—H14A	0.9300
C6—H6	0.9300	C14A—H14B	0.9300
C7—H7	0.9300	C13B—C14B	1.3331 (10)
C8—C9	1.344 (3)	C13B—H13B	0.9300
C8—H8	0.9300	C14B—H14C	0.9300
C9—C10	1.482 (3)	C14B—H14D	0.9300
C9—S2	1.750 (2)
C2—C1—H1A	109.5	O1—C10—N1	123.1 (2)
C2—C1—H1B	109.5	O1—C10—C9	126.5 (2)
H1A—C1—H1B	109.5	N1—C10—C9	110.46 (18)
C2—C1—H1C	109.5	N1—C11—S1	127.64 (18)
H1A—C1—H1C	109.5	N1—C11—S2	110.78 (16)
H1B—C1—H1C	109.5	S1—C11—S2	121.58 (15)
C3—C2—C7	117.3 (2)	C13B—C12—N1	119.7 (3)
C3—C2—C1	121.3 (2)	N1—C12—C13A	103.2 (5)
C7—C2—C1	121.4 (2)	N1—C12—H12A	111.1
C4—C3—C2	121.4 (2)	C13A—C12—H12A	111.1
C4—C3—H3	119.3	N1—C12—H12B	111.1
C2—C3—H3	119.3	C13A—C12—H12B	111.1
C3—C4—C5	121.4 (2)	H12A—C12—H12B	109.1
C3—C4—H4	119.3	C14A—C13A—C12	126.8 (11)
C5—C4—H4	119.3	C14A—C13A—H13A	116.6
C6—C5—C4	117.1 (2)	C12—C13A—H13A	116.6
C6—C5—C8	124.73 (19)	C13A—C14A—H14A	120.0
C4—C5—C8	118.14 (19)	C13A—C14A—H14B	120.0
C7—C6—C5	120.8 (2)	H14A—C14A—H14B	120.0
C7—C6—H6	119.6	C14B—C13B—C12	123.2 (7)
C5—C6—H6	119.6	C14B—C13B—H13B	118.4
C6—C7—C2	121.8 (2)	C12—C13B—H13B	118.4
C6—C7—H7	119.1	C13B—C14B—H14C	120.0
C2—C7—H7	119.1	C13B—C14B—H14D	120.0
C9—C8—C5	131.6 (2)	H14C—C14B—H14D	120.0
C9—C8—H8	114.2	C11—N1—C10	116.69 (19)
C5—C8—H8	114.2	C11—N1—C12	123.1 (2)
C8—C9—C10	120.57 (19)	C10—N1—C12	120.2 (2)
C8—C9—S2	130.12 (17)	C9—S2—C11	92.73 (10)
C10—C9—S2	109.31 (15)