3-Benzyl-5-benzyl­idene-2-sulfanylidene-1,3-thia­zolidin-4-one

Abstract

In the title mol­ecule, C₁₇H₁₃NOS₂, the essentially planar thia­zole 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 _r = 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) ų

• 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

• Δρ_max = 0.28 e Å⁻³

• Δρ_min = −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.

Supplementary Material

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

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

supplementary crystallographic information

Comment

The crystal structure determination of the title compound (I) is a countinuation of our work on thiazolidinone derivatives (Shahwar et al., 2009, 2011).

The molecular structure of the title compound is shown in Fig. 1. The essentially planar thiazole ring [r.m.s deviation 0.005 Å] forms dihedral angles of 16.85 (8)° and 75.02 (8)° with the C5-C10 and C12-C17 phenyl rings, respectively. The dihedral angle between the two phenyl rings is 61.95 (9)°.

Experimental

The title compound was prepared following a previously published method (Shahwar et al., 2009). X-ray quality crystals were grown from a solution of the title compound in n-hexane:ethylacetate:methanol (6:3:1).

Refinement

All H atoms were positioned with idealized geometry with C—H = 0.93 - 0.97 Å and were refined using a riding model with U_iso(H) = 1.2 U_eq(C). Four reflections 1 1 0, 0 0 1, 2 2 0 & 0 1 0 were omitted in the final refinemnt as they were obscured by the beamstop.

Figures

Fig. 1.

The molecular structure of (I) with thermal ellipsoids drawn at the 50% probability level.

Crystal data

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

Data collection

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

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

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, °)

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)