3-Benzyl-2-phenyl-1,3-thia-zolidin-4-one.

In the title compound, C(16)H(15)NOS, the thia-zolidine ring, which is essentially planar [maximum deviation = 0.071 (2) Å], makes dihedral angles of 88.01 (8) and 87.21 (8)° with the terminal phenyl rings. The dihedral angle between the phenyl rings is 49.45 (5)°. In the crystal, mol-ecules are linked by a weak inter-molecular C-H⋯O hydrogen bond, forming a supra-molecular chain along the b axis. Furthermore, the crystal packing is stabilized by a weak C-H⋯π inter-action.

Related literature

For details and applications of thia­zolidine-4-ones, see: Dutta et al. (1990 ▶); Jadhav & Ingle (1978 ▶); Gursoy & Terzioglu (2005 ▶); Rawal et al. (2007 ▶); Shrivastava et al. (2005 ▶); Look et al. (1996 ▶); Anders et al. (2001 ▶); Barreca et al. (2001 ▶); Diurno et al. (1992 ▶).

Experimental

Crystal data

C16H15NOS

M = 269.35

Monoclinic,

a = 13.5734 (15) Å

b = 10.1402 (11) Å

c = 10.1496 (11) Å

β = 104.305 (2)°

V = 1353.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.41 × 0.19 × 0.06 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.913, T max = 0.985

21164 measured reflections

3990 independent reflections

2813 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.112

S = 1.05

3990 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037706/is2778sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037706/is2778Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037706/is2778Isup3.cml

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

C16H15NOS	F(000) = 568
Mr = 269.35	Dx = 1.322 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4044 reflections
a = 13.5734 (15) Å	θ = 2.9–24.9°
b = 10.1402 (11) Å	µ = 0.23 mm−1
c = 10.1496 (11) Å	T = 296 K
β = 104.305 (2)°	Plate, colourless
V = 1353.6 (3) Å3	0.41 × 0.19 × 0.06 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	3990 independent reflections
Radiation source: fine-focus sealed tube	2813 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 30.2°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
Tmin = 0.913, Tmax = 0.985	k = −14→14
21164 measured reflections	l = −14→14

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0448P)2 + 0.2789P] where P = (Fo2 + 2Fc2)/3
3990 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.25 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	0.04954 (3)	0.22379 (4)	0.22886 (4)	0.04505 (12)
O1	0.16669 (11)	0.46692 (11)	0.51751 (13)	0.0650 (4)
N1	0.21308 (9)	0.28385 (11)	0.41853 (12)	0.0389 (3)
C1	0.34627 (12)	0.44309 (17)	0.30014 (17)	0.0510 (4)
H1A	0.2783	0.4676	0.2838	0.061*
C2	0.40708 (14)	0.49962 (19)	0.22451 (19)	0.0582 (4)
H2A	0.3798	0.5617	0.1580	0.070*
C3	0.50706 (14)	0.4646 (2)	0.2471 (2)	0.0637 (5)
H3A	0.5481	0.5024	0.1963	0.076*
C4	0.54623 (15)	0.3732 (2)	0.3454 (3)	0.0810 (7)
H4A	0.6143	0.3492	0.3613	0.097*
C5	0.48589 (14)	0.3161 (2)	0.4212 (2)	0.0650 (5)
H5A	0.5136	0.2538	0.4873	0.078*
C6	0.38484 (11)	0.35067 (14)	0.39972 (15)	0.0410 (3)
C7	0.32037 (12)	0.29270 (17)	0.48752 (16)	0.0479 (4)
H7A	0.3454	0.2052	0.5166	0.057*
H7B	0.3278	0.3467	0.5683	0.057*
C8	0.14552 (12)	0.37589 (14)	0.43636 (15)	0.0434 (3)
C9	0.04128 (13)	0.35455 (17)	0.34511 (19)	0.0533 (4)
H9A	0.0173	0.4347	0.2953	0.064*
H9B	−0.0061	0.3309	0.3987	0.064*
C10	0.17936 (10)	0.17886 (13)	0.32051 (14)	0.0358 (3)
H10A	0.2225	0.1788	0.2560	0.043*
C11	0.18426 (10)	0.04347 (13)	0.38516 (13)	0.0350 (3)
C12	0.14070 (11)	0.02045 (14)	0.49347 (15)	0.0420 (3)
H12A	0.1104	0.0896	0.5291	0.050*
C13	0.14219 (12)	−0.10439 (16)	0.54857 (17)	0.0499 (4)
H13A	0.1127	−0.1188	0.6209	0.060*
C14	0.18706 (13)	−0.20754 (16)	0.49698 (19)	0.0547 (4)
H14A	0.1879	−0.2915	0.5342	0.066*
C15	0.23077 (14)	−0.18557 (16)	0.38958 (19)	0.0561 (4)
H15A	0.2611	−0.2550	0.3544	0.067*
C16	0.22959 (12)	−0.06032 (15)	0.33392 (16)	0.0455 (4)
H16A	0.2594	−0.0461	0.2619	0.055*

	U11	U22	U33	U12	U13	U23
S1	0.0441 (2)	0.0416 (2)	0.0451 (2)	−0.00081 (16)	0.00278 (16)	0.00479 (16)
O1	0.0919 (10)	0.0400 (6)	0.0633 (7)	−0.0033 (6)	0.0195 (7)	−0.0119 (6)
N1	0.0399 (6)	0.0325 (6)	0.0436 (6)	−0.0060 (5)	0.0088 (5)	−0.0002 (5)
C1	0.0404 (8)	0.0553 (10)	0.0561 (9)	0.0005 (7)	0.0099 (7)	0.0130 (7)
C2	0.0548 (10)	0.0599 (11)	0.0594 (10)	−0.0048 (8)	0.0132 (8)	0.0154 (8)
C3	0.0508 (10)	0.0721 (13)	0.0721 (12)	−0.0090 (9)	0.0225 (9)	0.0089 (10)
C4	0.0441 (10)	0.0872 (16)	0.1158 (18)	0.0105 (10)	0.0273 (11)	0.0296 (14)
C5	0.0480 (10)	0.0596 (11)	0.0852 (13)	0.0083 (8)	0.0119 (9)	0.0229 (10)
C6	0.0383 (7)	0.0363 (7)	0.0452 (8)	−0.0057 (6)	0.0041 (6)	−0.0011 (6)
C7	0.0456 (8)	0.0481 (9)	0.0450 (8)	−0.0090 (7)	0.0020 (7)	0.0074 (7)
C8	0.0561 (9)	0.0309 (7)	0.0462 (8)	−0.0036 (6)	0.0185 (7)	0.0023 (6)
C9	0.0496 (9)	0.0456 (9)	0.0662 (10)	0.0059 (7)	0.0173 (8)	−0.0016 (8)
C10	0.0372 (7)	0.0346 (7)	0.0369 (7)	−0.0029 (5)	0.0117 (5)	−0.0001 (5)
C11	0.0339 (7)	0.0319 (6)	0.0382 (7)	−0.0008 (5)	0.0069 (5)	−0.0012 (5)
C12	0.0450 (8)	0.0365 (7)	0.0472 (8)	−0.0005 (6)	0.0165 (6)	0.0010 (6)
C13	0.0495 (9)	0.0448 (9)	0.0555 (9)	−0.0074 (7)	0.0130 (7)	0.0118 (7)
C14	0.0547 (10)	0.0337 (8)	0.0667 (11)	−0.0038 (7)	−0.0020 (8)	0.0079 (7)
C15	0.0611 (11)	0.0368 (8)	0.0649 (11)	0.0126 (7)	0.0050 (9)	−0.0067 (7)
C16	0.0471 (8)	0.0443 (8)	0.0451 (8)	0.0074 (7)	0.0111 (7)	−0.0034 (6)

S1—C9	1.7967 (17)	C7—H7A	0.9700
S1—C10	1.8352 (14)	C7—H7B	0.9700
O1—C8	1.2231 (18)	C8—C9	1.503 (2)
N1—C8	1.3515 (19)	C9—H9A	0.9700
N1—C10	1.4518 (18)	C9—H9B	0.9700
N1—C7	1.4544 (19)	C10—C11	1.5160 (19)
C1—C2	1.383 (2)	C10—H10A	0.9800
C1—C6	1.383 (2)	C11—C16	1.3838 (19)
C1—H1A	0.9300	C11—C12	1.391 (2)
C2—C3	1.366 (3)	C12—C13	1.382 (2)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.369 (3)	C13—C14	1.377 (2)
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.382 (3)	C14—C15	1.382 (3)
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.380 (2)	C15—C16	1.389 (2)
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.513 (2)	C16—H16A	0.9300
C9—S1—C10	93.34 (7)	C8—C9—S1	107.99 (11)
C8—N1—C10	119.26 (12)	C8—C9—H9A	110.1
C8—N1—C7	121.65 (13)	S1—C9—H9A	110.1
C10—N1—C7	118.93 (12)	C8—C9—H9B	110.1
C2—C1—C6	121.10 (15)	S1—C9—H9B	110.1
C2—C1—H1A	119.4	H9A—C9—H9B	108.4
C6—C1—H1A	119.4	N1—C10—C11	113.25 (11)
C3—C2—C1	120.23 (17)	N1—C10—S1	105.43 (9)
C3—C2—H2A	119.9	C11—C10—S1	112.22 (9)
C1—C2—H2A	119.9	N1—C10—H10A	108.6
C2—C3—C4	119.27 (17)	C11—C10—H10A	108.6
C2—C3—H3A	120.4	S1—C10—H10A	108.6
C4—C3—H3A	120.4	C16—C11—C12	119.00 (13)
C3—C4—C5	120.83 (18)	C16—C11—C10	120.14 (13)
C3—C4—H4A	119.6	C12—C11—C10	120.83 (12)
C5—C4—H4A	119.6	C13—C12—C11	120.47 (14)
C6—C5—C4	120.54 (17)	C13—C12—H12A	119.8
C6—C5—H5A	119.7	C11—C12—H12A	119.8
C4—C5—H5A	119.7	C14—C13—C12	120.36 (16)
C5—C6—C1	118.02 (15)	C14—C13—H13A	119.8
C5—C6—C7	120.33 (14)	C12—C13—H13A	119.8
C1—C6—C7	121.60 (14)	C13—C14—C15	119.60 (15)
N1—C7—C6	113.35 (12)	C13—C14—H14A	120.2
N1—C7—H7A	108.9	C15—C14—H14A	120.2
C6—C7—H7A	108.9	C14—C15—C16	120.29 (15)
N1—C7—H7B	108.9	C14—C15—H15A	119.9
C6—C7—H7B	108.9	C16—C15—H15A	119.9
H7A—C7—H7B	107.7	C11—C16—C15	120.28 (15)
O1—C8—N1	123.85 (15)	C11—C16—H16A	119.9
O1—C8—C9	123.53 (15)	C15—C16—H16A	119.9
N1—C8—C9	112.62 (13)
C6—C1—C2—C3	0.1 (3)	C8—N1—C10—C11	−114.56 (14)
C1—C2—C3—C4	−0.1 (3)	C7—N1—C10—C11	69.99 (16)
C2—C3—C4—C5	0.2 (4)	C8—N1—C10—S1	8.50 (15)
C3—C4—C5—C6	−0.3 (4)	C7—N1—C10—S1	−166.95 (10)
C4—C5—C6—C1	0.3 (3)	C9—S1—C10—N1	−10.43 (10)
C4—C5—C6—C7	−177.10 (19)	C9—S1—C10—C11	113.28 (11)
C2—C1—C6—C5	−0.2 (3)	N1—C10—C11—C16	−131.16 (14)
C2—C1—C6—C7	177.17 (16)	S1—C10—C11—C16	109.62 (13)
C8—N1—C7—C6	−98.30 (17)	N1—C10—C11—C12	50.93 (18)
C10—N1—C7—C6	77.04 (17)	S1—C10—C11—C12	−68.30 (15)
C5—C6—C7—N1	−151.78 (16)	C16—C11—C12—C13	−0.4 (2)
C1—C6—C7—N1	30.9 (2)	C10—C11—C12—C13	177.59 (13)
C10—N1—C8—O1	179.17 (14)	C11—C12—C13—C14	0.1 (2)
C7—N1—C8—O1	−5.5 (2)	C12—C13—C14—C15	0.0 (3)
C10—N1—C8—C9	−1.01 (18)	C13—C14—C15—C16	0.0 (3)
C7—N1—C8—C9	174.31 (13)	C12—C11—C16—C15	0.4 (2)
O1—C8—C9—S1	172.54 (13)	C10—C11—C16—C15	−177.53 (14)
N1—C8—C9—S1	−7.28 (16)	C14—C15—C16—C11	−0.3 (2)
C10—S1—C9—C8	10.22 (12)

Cg1 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1i	0.93	2.47	3.323 (2)	153
C2—H2A···Cg1ii	0.93	2.99	3.705 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O1i	0.93	2.47	3.323 (2)	153
C2—H2A⋯Cg1ii	0.93	2.99	3.705 (3)	134

Symmetry codes: (i) ; (ii) .