3-Benzyl-5-benzyl-idene-2-sulfanylidene-1,3-thia-zolidin-4-one.

In the title mol-ecule, C(17)H(13)NOS(2), the essentially planar thia-zole ring (r.m.s deviation 0.005 Å) forms dihedral angles of 16.85 (8)° and 75.02 (8)° with the phenyl rings. The dihedral angle between the two phenyl rings is 61.95 (9)°.

Related literature

For the synthesis and related structures, see: Shahwar et al. (2009 ▶, 2011 ▶).

Experimental

Crystal data

C17H13NOS2

M = 311.40

Triclinic,

a = 6.3152 (2) Å

b = 10.8168 (3) Å

c = 11.4545 (3) Å

α = 84.1150 (9)°

β = 77.6000 (9)°

γ = 76.1770 (9)°

V = 740.99 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 296 K

0.35 × 0.31 × 0.15 mm

Data collection

Bruker Kappa APEX II CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.886, T max = 0.949

13205 measured reflections

3583 independent reflections

2930 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 1.03

3583 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.26 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811027450/lh5281sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027450/lh5281Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027450/lh5281Isup3.cml

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

C17H13NOS2	Z = 2
Mr = 311.40	F(000) = 324
Triclinic, P1	Dx = 1.396 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3152 (2) Å	Cell parameters from 6403 reflections
b = 10.8168 (3) Å	θ = 2.6–28.3°
c = 11.4545 (3) Å	µ = 0.36 mm−1
α = 84.1150 (9)°	T = 296 K
β = 77.6000 (9)°	Needle, pale yellow
γ = 76.1770 (9)°	0.35 × 0.31 × 0.15 mm
V = 740.99 (4) Å3

Bruker KAPPA APEX II CCD diffractometer	3583 independent reflections
Radiation source: fine-focus sealed tube	2930 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 28.4°, θmin = 3.4°
Absorption correction: multi-scan (SADABS;Bruker, 2007)	h = −8→8
Tmin = 0.886, Tmax = 0.949	k = −14→14
13205 measured reflections	l = −15→15

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) = 0.101	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.048P)2 + 0.1921P] where P = (Fo2 + 2Fc2)/3
3583 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.36101 (6)	0.34929 (4)	0.98088 (4)	0.04416 (12)
S2	0.24747 (8)	0.57799 (4)	0.82368 (4)	0.05631 (14)
O1	−0.0562 (2)	0.18668 (12)	0.89696 (10)	0.0518 (3)
N1	0.06938 (19)	0.37139 (12)	0.85045 (10)	0.0382 (3)
C3	0.2282 (2)	0.22259 (14)	0.99118 (13)	0.0374 (3)
C4	0.2515 (2)	0.11550 (14)	1.06168 (13)	0.0401 (3)
H4	0.1636	0.0602	1.0540	0.048*
C12	0.0019 (3)	0.36707 (14)	0.64596 (13)	0.0414 (3)
C5	0.3954 (2)	0.07342 (14)	1.14880 (13)	0.0401 (3)
C1	0.2109 (2)	0.43656 (15)	0.87728 (13)	0.0395 (3)
C2	0.0659 (2)	0.25206 (14)	0.91071 (12)	0.0384 (3)
C11	−0.0820 (2)	0.42216 (15)	0.76689 (13)	0.0430 (3)
H11A	−0.1013	0.5141	0.7575	0.052*
H11B	−0.2263	0.4036	0.8007	0.052*
C6	0.5720 (3)	0.12723 (16)	1.15454 (15)	0.0481 (4)
H6	0.6061	0.1920	1.0989	0.058*
C10	0.3525 (3)	−0.02573 (16)	1.23169 (16)	0.0529 (4)
H10	0.2383	−0.0650	1.2282	0.063*
C7	0.6974 (3)	0.08547 (18)	1.24193 (17)	0.0554 (4)
H7	0.8146	0.1226	1.2448	0.066*
C13	−0.1276 (3)	0.30505 (19)	0.60087 (17)	0.0594 (5)
H13	−0.2644	0.2959	0.6464	0.071*
C17	0.2039 (3)	0.38009 (18)	0.57709 (15)	0.0541 (4)
H17	0.2924	0.4226	0.6058	0.065*
C8	0.6501 (3)	−0.01051 (19)	1.32454 (18)	0.0611 (5)
H8	0.7336	−0.0378	1.3838	0.073*
C9	0.4783 (3)	−0.06585 (19)	1.31873 (19)	0.0651 (5)
H9	0.4466	−0.1312	1.3742	0.078*
C16	0.2752 (4)	0.3298 (2)	0.46494 (17)	0.0692 (6)
H16	0.4123	0.3378	0.4190	0.083*
C14	−0.0563 (5)	0.2564 (2)	0.4888 (2)	0.0784 (6)
H14	−0.1455	0.2152	0.4591	0.094*
C15	0.1443 (4)	0.2685 (2)	0.42184 (18)	0.0751 (7)
H15	0.1925	0.2351	0.3466	0.090*

	U11	U22	U33	U12	U13	U23
S1	0.0472 (2)	0.0448 (2)	0.0463 (2)	−0.01693 (16)	−0.01683 (16)	0.00314 (16)
S2	0.0700 (3)	0.0434 (2)	0.0624 (3)	−0.0228 (2)	−0.0220 (2)	0.00817 (19)
O1	0.0605 (7)	0.0539 (7)	0.0511 (7)	−0.0274 (5)	−0.0180 (5)	0.0010 (5)
N1	0.0415 (6)	0.0407 (7)	0.0344 (6)	−0.0112 (5)	−0.0093 (5)	−0.0016 (5)
C3	0.0404 (7)	0.0390 (7)	0.0334 (7)	−0.0110 (6)	−0.0054 (5)	−0.0041 (6)
C4	0.0456 (7)	0.0387 (7)	0.0369 (7)	−0.0114 (6)	−0.0061 (6)	−0.0053 (6)
C12	0.0501 (8)	0.0369 (7)	0.0364 (7)	−0.0052 (6)	−0.0152 (6)	0.0044 (6)
C5	0.0463 (7)	0.0344 (7)	0.0368 (7)	−0.0052 (6)	−0.0057 (6)	−0.0042 (6)
C1	0.0400 (7)	0.0418 (8)	0.0370 (7)	−0.0104 (6)	−0.0062 (6)	−0.0030 (6)
C2	0.0422 (7)	0.0427 (8)	0.0315 (7)	−0.0130 (6)	−0.0048 (5)	−0.0041 (6)
C11	0.0418 (7)	0.0464 (8)	0.0405 (8)	−0.0062 (6)	−0.0122 (6)	−0.0012 (6)
C6	0.0473 (8)	0.0483 (9)	0.0473 (9)	−0.0127 (7)	−0.0089 (7)	0.0082 (7)
C10	0.0631 (10)	0.0402 (8)	0.0598 (11)	−0.0171 (7)	−0.0197 (8)	0.0070 (7)
C7	0.0489 (9)	0.0575 (10)	0.0623 (11)	−0.0131 (7)	−0.0194 (8)	0.0050 (8)
C13	0.0733 (12)	0.0610 (11)	0.0518 (10)	−0.0236 (9)	−0.0208 (9)	−0.0012 (8)
C17	0.0549 (9)	0.0590 (11)	0.0459 (9)	−0.0099 (8)	−0.0092 (7)	0.0005 (8)
C8	0.0641 (11)	0.0582 (11)	0.0634 (11)	−0.0091 (8)	−0.0294 (9)	0.0113 (9)
C9	0.0786 (13)	0.0512 (10)	0.0684 (12)	−0.0191 (9)	−0.0279 (10)	0.0232 (9)
C16	0.0730 (12)	0.0707 (13)	0.0467 (10)	0.0048 (10)	−0.0005 (9)	0.0020 (9)
C14	0.1163 (19)	0.0720 (14)	0.0588 (13)	−0.0261 (13)	−0.0332 (13)	−0.0124 (10)
C15	0.1135 (19)	0.0592 (12)	0.0438 (10)	0.0038 (12)	−0.0195 (11)	−0.0085 (9)

S1—C1	1.7390 (15)	C6—C7	1.382 (2)
S1—C3	1.7517 (15)	C6—H6	0.9300
S2—C1	1.6389 (16)	C10—C9	1.379 (2)
O1—C2	1.2066 (18)	C10—H10	0.9300
N1—C1	1.3614 (19)	C7—C8	1.374 (3)
N1—C2	1.4026 (19)	C7—H7	0.9300
N1—C11	1.4715 (18)	C13—C14	1.380 (3)
C3—C4	1.339 (2)	C13—H13	0.9300
C3—C2	1.480 (2)	C17—C16	1.388 (3)
C4—C5	1.459 (2)	C17—H17	0.9300
C4—H4	0.9300	C8—C9	1.374 (3)
C12—C13	1.378 (2)	C8—H8	0.9300
C12—C17	1.379 (2)	C9—H9	0.9300
C12—C11	1.503 (2)	C16—C15	1.368 (3)
C5—C6	1.392 (2)	C16—H16	0.9300
C5—C10	1.395 (2)	C14—C15	1.361 (3)
C11—H11A	0.9700	C14—H14	0.9300
C11—H11B	0.9700	C15—H15	0.9300
C1—S1—C3	92.81 (7)	C7—C6—H6	119.6
C1—N1—C2	116.64 (12)	C5—C6—H6	119.6
C1—N1—C11	123.42 (13)	C9—C10—C5	120.40 (16)
C2—N1—C11	119.89 (12)	C9—C10—H10	119.8
C4—C3—C2	121.65 (13)	C5—C10—H10	119.8
C4—C3—S1	128.94 (12)	C8—C7—C6	120.44 (17)
C2—C3—S1	109.35 (10)	C8—C7—H7	119.8
C3—C4—C5	129.10 (14)	C6—C7—H7	119.8
C3—C4—H4	115.5	C12—C13—C14	120.65 (19)
C5—C4—H4	115.5	C12—C13—H13	119.7
C13—C12—C17	118.90 (16)	C14—C13—H13	119.7
C13—C12—C11	119.66 (15)	C12—C17—C16	120.04 (18)
C17—C12—C11	121.41 (15)	C12—C17—H17	120.0
C6—C5—C10	118.12 (14)	C16—C17—H17	120.0
C6—C5—C4	123.75 (14)	C7—C8—C9	119.40 (16)
C10—C5—C4	118.12 (14)	C7—C8—H8	120.3
N1—C1—S2	127.66 (12)	C9—C8—H8	120.3
N1—C1—S1	111.06 (11)	C8—C9—C10	120.86 (17)
S2—C1—S1	121.28 (9)	C8—C9—H9	119.6
O1—C2—N1	122.92 (13)	C10—C9—H9	119.6
O1—C2—C3	126.97 (14)	C15—C16—C17	120.2 (2)
N1—C2—C3	110.11 (12)	C15—C16—H16	119.9
N1—C11—C12	112.72 (12)	C17—C16—H16	119.9
N1—C11—H11A	109.0	C15—C14—C13	120.1 (2)
C12—C11—H11A	109.0	C15—C14—H14	119.9
N1—C11—H11B	109.0	C13—C14—H14	119.9
C12—C11—H11B	109.0	C14—C15—C16	120.13 (19)
H11A—C11—H11B	107.8	C14—C15—H15	119.9
C7—C6—C5	120.75 (15)	C16—C15—H15	119.9
C1—S1—C3—C4	−176.86 (14)	C1—N1—C11—C12	101.92 (16)
C1—S1—C3—C2	0.27 (11)	C2—N1—C11—C12	−80.68 (17)
C2—C3—C4—C5	−177.53 (14)	C13—C12—C11—N1	122.62 (16)
S1—C3—C4—C5	−0.7 (2)	C17—C12—C11—N1	−59.2 (2)
C3—C4—C5—C6	−14.8 (2)	C10—C5—C6—C7	−1.6 (2)
C3—C4—C5—C10	164.69 (16)	C4—C5—C6—C7	177.88 (15)
C2—N1—C1—S2	−178.75 (11)	C6—C5—C10—C9	1.9 (3)
C11—N1—C1—S2	−1.3 (2)	C4—C5—C10—C9	−177.57 (16)
C2—N1—C1—S1	1.48 (16)	C5—C6—C7—C8	0.3 (3)
C11—N1—C1—S1	178.95 (10)	C17—C12—C13—C14	0.2 (3)
C3—S1—C1—N1	−0.97 (11)	C11—C12—C13—C14	178.45 (17)
C3—S1—C1—S2	179.24 (10)	C13—C12—C17—C16	−0.8 (3)
C1—N1—C2—O1	178.07 (14)	C11—C12—C17—C16	−179.01 (15)
C11—N1—C2—O1	0.5 (2)	C6—C7—C8—C9	0.8 (3)
C1—N1—C2—C3	−1.27 (17)	C7—C8—C9—C10	−0.4 (3)
C11—N1—C2—C3	−178.83 (12)	C5—C10—C9—C8	−1.0 (3)
C4—C3—C2—O1	−1.5 (2)	C12—C17—C16—C15	0.8 (3)
S1—C3—C2—O1	−178.84 (13)	C12—C13—C14—C15	0.4 (3)
C4—C3—C2—N1	177.84 (13)	C13—C14—C15—C16	−0.5 (3)
S1—C3—C2—N1	0.46 (14)	C17—C16—C15—C14	−0.1 (3)