(5Z)-5-(2-Methyl-benzyl-idene)-3-phenyl-2-thioxo-1,3-thia-zolidin-4-one.

In the title compound, C(17)H(13)NOS(2), the heterocyclic ring is oriented at a dihedral angle of 74.43 (5)° with respect to the anilinic benzene ring and at a dihedral angle of 17.31 (9)° with respect to phenyl ring. An intra-molecular C-H⋯S inter-action occurs, resulting in an S(6) ring. In the crystal, the packing is consolidated by C-H⋯π inter-actions and possible very weak aromatic π-π stacking [centroid-centroid separation = 4.025 (1) Å].

Related literature

For related structures, see: Linden et al. (1999 ▶); Shahwar et al. (2009a ▶,b ▶,c ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H13NOS2

M = 311.40

Monoclinic,

a = 9.8317 (4) Å

b = 16.6317 (6) Å

c = 9.3865 (4) Å

β = 93.541 (2)°

V = 1531.93 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 296 K

0.40 × 0.30 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.879, T max = 0.941

17261 measured reflections

3807 independent reflections

2879 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.104

S = 1.01

3807 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (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: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044304/hb5181sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044304/hb5181Isup2.hkl

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

C17H13NOS2	F(000) = 648
Mr = 311.40	Dx = 1.350 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3807 reflections
a = 9.8317 (4) Å	θ = 2.1–28.3°
b = 16.6317 (6) Å	µ = 0.35 mm−1
c = 9.3865 (4) Å	T = 296 K
β = 93.541 (2)°	Prisms, yellow
V = 1531.93 (11) Å3	0.40 × 0.30 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3807 independent reflections
Radiation source: fine-focus sealed tube	2879 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 7.40 pixels mm-1	θmax = 28.3°, θmin = 2.1°
ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→22
Tmin = 0.879, Tmax = 0.941	l = −12→9
17261 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.3691P] where P = (Fo2 + 2Fc2)/3
3807 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.95527 (4)	0.36087 (3)	0.48338 (4)	0.0408 (1)
S2	0.81145 (5)	0.25140 (3)	0.66855 (5)	0.0544 (2)
O1	0.62790 (12)	0.44603 (8)	0.30111 (16)	0.0590 (5)
N1	0.69362 (13)	0.35311 (8)	0.47353 (15)	0.0379 (4)
C1	0.55749 (16)	0.32728 (10)	0.49995 (18)	0.0409 (5)
C2	0.47556 (18)	0.37600 (11)	0.5756 (2)	0.0508 (6)
C3	0.3467 (2)	0.34908 (14)	0.6034 (3)	0.0648 (8)
C4	0.3022 (2)	0.27496 (15)	0.5571 (3)	0.0686 (8)
C5	0.3841 (2)	0.22789 (15)	0.4798 (3)	0.0774 (9)
C6	0.5136 (2)	0.25369 (12)	0.4493 (3)	0.0644 (8)
C7	0.71757 (16)	0.41175 (9)	0.37026 (18)	0.0400 (5)
C8	0.86629 (15)	0.42329 (9)	0.36025 (17)	0.0358 (5)
C9	0.80674 (16)	0.32015 (9)	0.54449 (17)	0.0374 (5)
C10	0.91369 (16)	0.47413 (9)	0.26411 (18)	0.0390 (5)
C11	1.05266 (15)	0.49045 (10)	0.22684 (17)	0.0383 (5)
C12	1.07841 (16)	0.55752 (10)	0.14107 (17)	0.0393 (5)
C13	1.20990 (18)	0.56853 (12)	0.0986 (2)	0.0522 (6)
C14	1.31437 (18)	0.51669 (14)	0.1394 (2)	0.0591 (7)
C15	1.29056 (18)	0.45192 (13)	0.2249 (2)	0.0580 (7)
C16	1.16070 (17)	0.43879 (12)	0.2676 (2)	0.0509 (6)
C17	0.96876 (19)	0.61723 (10)	0.0967 (2)	0.0500 (6)
H2	0.50600	0.42618	0.60750	0.0609*
H3	0.28976	0.38161	0.65410	0.0777*
H4	0.21635	0.25676	0.57835	0.0823*
H5	0.35298	0.17800	0.44709	0.0929*
H6	0.56916	0.22185	0.39589	0.0773*
H10	0.84702	0.50379	0.21293	0.0468*
H13	1.22796	0.61221	0.04085	0.0626*
H14	1.40133	0.52561	0.10891	0.0709*
H15	1.36121	0.41725	0.25365	0.0695*
H16	1.14447	0.39461	0.32487	0.0611*
H17A	1.00596	0.65805	0.03813	0.0751*
H17B	0.93458	0.64157	0.18005	0.0751*
H17C	0.89582	0.59014	0.04357	0.0751*

	U11	U22	U33	U12	U13	U23
S1	0.0330 (2)	0.0478 (2)	0.0411 (2)	0.0007 (2)	−0.0014 (2)	0.0040 (2)
S2	0.0639 (3)	0.0516 (3)	0.0477 (3)	−0.0025 (2)	0.0028 (2)	0.0119 (2)
O1	0.0342 (6)	0.0622 (8)	0.0804 (10)	0.0084 (6)	0.0030 (6)	0.0248 (7)
N1	0.0321 (7)	0.0371 (7)	0.0450 (8)	−0.0012 (5)	0.0062 (5)	0.0000 (6)
C1	0.0342 (8)	0.0439 (9)	0.0451 (9)	−0.0024 (7)	0.0059 (7)	0.0020 (7)
C2	0.0418 (9)	0.0535 (10)	0.0578 (11)	0.0034 (8)	0.0089 (8)	−0.0037 (9)
C3	0.0432 (11)	0.0808 (15)	0.0722 (14)	0.0103 (10)	0.0183 (10)	0.0057 (12)
C4	0.0382 (10)	0.0817 (15)	0.0866 (16)	−0.0095 (10)	0.0095 (10)	0.0170 (13)
C5	0.0572 (13)	0.0668 (14)	0.109 (2)	−0.0241 (11)	0.0110 (13)	−0.0107 (14)
C6	0.0501 (11)	0.0584 (12)	0.0864 (16)	−0.0107 (9)	0.0177 (11)	−0.0182 (11)
C7	0.0341 (8)	0.0369 (8)	0.0495 (9)	0.0031 (6)	0.0066 (7)	0.0013 (7)
C8	0.0321 (8)	0.0346 (8)	0.0408 (8)	0.0034 (6)	0.0023 (6)	−0.0016 (6)
C9	0.0396 (8)	0.0364 (8)	0.0363 (8)	−0.0013 (6)	0.0035 (6)	−0.0048 (6)
C10	0.0330 (8)	0.0390 (8)	0.0451 (9)	0.0053 (6)	0.0026 (7)	0.0011 (7)
C11	0.0330 (8)	0.0445 (8)	0.0374 (8)	0.0006 (7)	0.0025 (6)	−0.0017 (7)
C12	0.0378 (8)	0.0421 (8)	0.0379 (9)	−0.0053 (7)	0.0022 (7)	−0.0042 (7)
C13	0.0482 (10)	0.0555 (11)	0.0535 (11)	−0.0121 (8)	0.0076 (8)	0.0006 (9)
C14	0.0343 (9)	0.0815 (14)	0.0623 (12)	−0.0096 (9)	0.0106 (8)	−0.0051 (11)
C15	0.0336 (9)	0.0813 (14)	0.0589 (12)	0.0108 (9)	0.0014 (8)	0.0055 (10)
C16	0.0383 (9)	0.0640 (12)	0.0508 (10)	0.0069 (8)	0.0060 (8)	0.0122 (9)
C17	0.0530 (10)	0.0416 (9)	0.0556 (11)	−0.0013 (8)	0.0043 (8)	0.0059 (8)

S1—C8	1.7476 (16)	C12—C13	1.388 (2)
S1—C9	1.7389 (16)	C12—C17	1.506 (2)
S2—C9	1.6306 (16)	C13—C14	1.377 (3)
O1—C7	1.205 (2)	C14—C15	1.372 (3)
N1—C1	1.442 (2)	C15—C16	1.379 (2)
N1—C7	1.405 (2)	C2—H2	0.9300
N1—C9	1.375 (2)	C3—H3	0.9300
C1—C2	1.371 (2)	C4—H4	0.9300
C1—C6	1.373 (3)	C5—H5	0.9300
C2—C3	1.384 (3)	C6—H6	0.9300
C3—C4	1.370 (3)	C10—H10	0.9300
C4—C5	1.364 (3)	C13—H13	0.9300
C5—C6	1.390 (3)	C14—H14	0.9300
C7—C8	1.483 (2)	C15—H15	0.9300
C8—C10	1.341 (2)	C16—H16	0.9300
C10—C11	1.457 (2)	C17—H17A	0.9600
C11—C12	1.408 (2)	C17—H17B	0.9600
C11—C16	1.401 (2)	C17—H17C	0.9600
C8—S1—C9	93.05 (7)	C13—C14—C15	120.20 (17)
C1—N1—C7	121.49 (13)	C14—C15—C16	119.26 (18)
C1—N1—C9	121.99 (13)	C11—C16—C15	121.57 (18)
C7—N1—C9	116.49 (13)	C1—C2—H2	121.00
N1—C1—C2	119.62 (15)	C3—C2—H2	121.00
N1—C1—C6	118.77 (15)	C2—C3—H3	120.00
C2—C1—C6	121.60 (16)	C4—C3—H3	120.00
C1—C2—C3	118.72 (18)	C3—C4—H4	120.00
C2—C3—C4	120.6 (2)	C5—C4—H4	120.00
C3—C4—C5	119.9 (2)	C4—C5—H5	120.00
C4—C5—C6	120.7 (2)	C6—C5—H5	120.00
C1—C6—C5	118.4 (2)	C1—C6—H6	121.00
O1—C7—N1	123.48 (15)	C5—C6—H6	121.00
O1—C7—C8	126.56 (15)	C8—C10—H10	115.00
N1—C7—C8	109.96 (13)	C11—C10—H10	115.00
S1—C8—C7	109.66 (11)	C12—C13—H13	119.00
S1—C8—C10	129.72 (12)	C14—C13—H13	119.00
C7—C8—C10	120.60 (14)	C13—C14—H14	120.00
S1—C9—S2	121.42 (10)	C15—C14—H14	120.00
S1—C9—N1	110.83 (11)	C14—C15—H15	120.00
S2—C9—N1	127.74 (12)	C16—C15—H15	120.00
C8—C10—C11	130.48 (15)	C11—C16—H16	119.00
C10—C11—C12	119.31 (14)	C15—C16—H16	119.00
C10—C11—C16	121.79 (15)	C12—C17—H17A	109.00
C12—C11—C16	118.82 (14)	C12—C17—H17B	109.00
C11—C12—C13	118.18 (15)	C12—C17—H17C	109.00
C11—C12—C17	122.00 (14)	H17A—C17—H17B	109.00
C13—C12—C17	119.81 (15)	H17A—C17—H17C	109.00
C12—C13—C14	121.96 (18)	H17B—C17—H17C	109.00
C9—S1—C8—C7	0.70 (12)	C3—C4—C5—C6	1.1 (4)
C9—S1—C8—C10	−177.47 (16)	C4—C5—C6—C1	0.6 (4)
C8—S1—C9—S2	179.23 (11)	O1—C7—C8—S1	179.38 (15)
C8—S1—C9—N1	−0.06 (13)	O1—C7—C8—C10	−2.3 (3)
C7—N1—C1—C2	−75.8 (2)	N1—C7—C8—S1	−1.15 (16)
C7—N1—C1—C6	104.8 (2)	N1—C7—C8—C10	177.21 (14)
C9—N1—C1—C2	106.26 (19)	S1—C8—C10—C11	3.5 (3)
C9—N1—C1—C6	−73.2 (2)	C7—C8—C10—C11	−174.47 (16)
C1—N1—C7—O1	2.6 (2)	C8—C10—C11—C12	−168.06 (17)
C1—N1—C7—C8	−176.90 (14)	C8—C10—C11—C16	15.4 (3)
C9—N1—C7—O1	−179.33 (16)	C10—C11—C12—C13	−175.47 (16)
C9—N1—C7—C8	1.18 (19)	C10—C11—C12—C17	5.4 (2)
C1—N1—C9—S1	177.41 (12)	C16—C11—C12—C13	1.1 (2)
C1—N1—C9—S2	−1.8 (2)	C16—C11—C12—C17	−178.04 (16)
C7—N1—C9—S1	−0.66 (17)	C10—C11—C16—C15	176.08 (17)
C7—N1—C9—S2	−179.90 (13)	C12—C11—C16—C15	−0.5 (3)
N1—C1—C2—C3	−178.13 (18)	C11—C12—C13—C14	−0.8 (3)
C6—C1—C2—C3	1.3 (3)	C17—C12—C13—C14	178.36 (17)
N1—C1—C6—C5	177.6 (2)	C12—C13—C14—C15	−0.2 (3)
C2—C1—C6—C5	−1.8 (3)	C13—C14—C15—C16	0.9 (3)
C1—C2—C3—C4	0.5 (3)	C14—C15—C16—C11	−0.6 (3)
C2—C3—C4—C5	−1.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···S1	0.93	2.52	3.2197 (19)	133
C17—H17C···CgCi	0.96	2.72	3.569 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯S1	0.93	2.52	3.2197 (19)	133
C17—H17C⋯CgCi	0.96	2.72	3.569 (2)	148

Symmetry code: (i) . CgC is the centroid of C11–C16 benzene ring.