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

Shahwar, D.; Raza, M.A.; Aslam, S.; Mehmood, S.; Tariq, S.; Asiri, A.M.

doi:10.1107/S1600536811027450

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2083

doi:10.1107/S1600536811027450

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

Durre Shahwar,^a Muhammad Asam Raza,^a ^* Saherish Aslam,^a Sumbal Mehmood,^a Sidra Tariq ^a and Abdullah M. Asiri ^b

^aDepartment of Chemistry, Government Collge University, Lahore 54000, Pakistan, and ^bThe Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah, PO Box 80203, Saudi Arabia
^*Correspondence e-mail: asamgcu@yahoo.com

(Received 4 July 2011; accepted 8 July 2011; online 23 July 2011)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.036
wR(F²) = 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811027450/lh5281sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811027450/lh5281Isup3.cml

checkCIF report

Comment top

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)°.

Related literature top

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

Experimental top

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).

Computing details top

Data collection: APEXII (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2009).

Figures top

Fig. 1. The molecular structure of (I) with thermal ellipsoids drawn at the 50% probability level.

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

Crystal data top

C₁₇H₁₃NOS₂	Z = 2
M_r = 311.40	F(000) = 324
Triclinic, P1	D_x = 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 top

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

Refinement top

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(F_o²) + (0.048P)² + 0.1921P] where P = (F_o² + 2F_c²)/3
3583 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₇H₁₃NOS₂	γ = 76.1770 (9)°
M_r = 311.40	V = 740.99 (4) Å³
Triclinic, P1	Z = 2
a = 6.3152 (2) Å	Mo Kα radiation
b = 10.8168 (3) Å	µ = 0.36 mm⁻¹
c = 11.4545 (3) Å	T = 296 K
α = 84.1150 (9)°	0.35 × 0.31 × 0.15 mm
β = 77.6000 (9)°

Data collection top

Bruker KAPPA APEX II CCD diffractometer	3583 independent reflections
Absorption correction: multi-scan (SADABS;Bruker, 2007)	2930 reflections with I > 2σ(I)
T_min = 0.886, T_max = 0.949	R_int = 0.028
13205 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.03	Δρ_max = 0.28 e Å⁻³
3583 reflections	Δρ_min = −0.26 e Å⁻³
190 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃NOS₂
M_r	311.40
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.3152 (2), 10.8168 (3), 11.4545 (3)
α, β, γ (°)	84.1150 (9), 77.6000 (9), 76.1770 (9)
V (Å³)	740.99 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.35 × 0.31 × 0.15

Data collection
Diffractometer	Bruker KAPPA APEX II CCD diffractometer
Absorption correction	Multi-scan (SADABS;Bruker, 2007)
T_min, T_max	0.886, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	13205, 3583, 2930
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.101, 1.03
No. of reflections	3583
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.26

Computer programs: APEXII (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Acknowledgements

DS acknowledges Government College University, Lahore, for providing funds under the GCU-funded Research Projects Programme.

References

Bruker (2007). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Shahwar, D., Tahir, M. N., Raza, M. A., Ahmad, N. & Aslam, S. (2011). Acta Cryst. E67, o133. Web of Science CrossRef IUCr Journals Google Scholar
Shahwar, D., Tahir, M. N., Raza, M. A. & Iqbal, B. (2009). Acta Cryst. E65, o2917. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar