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

Shahwar, D.; Tahir, M.N.; Raza, M.A.; Ahmad, N.; Aslam, S.

doi:10.1107/S1600536810051548

organic compounds

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Volume 67| Part 1| January 2011| Page o133

https://doi.org/10.1107/S1600536810051548

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

Durre Shahwar,^a M. Nawaz Tahir,^b ^* Muhammad Asam Raza,^a Naeem Ahmad ^a and Saherish Aslam ^a

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 5 December 2010; accepted 9 December 2010; online 15 December 2010)

In the title compound, C₁₀H₉NOS₂, the five-membered heterocyclic ring and the benzyl moiety are oriented at a dihedral angle of 77.25 (4)°. In the crystal, infinite polymeric C(6) chains extending along [001] are formed due to C—H⋯O hydrogen bonds. C—H⋯π interactions link the chains, building up a three-dimensional network.

Related literature

For background to our interest in the sythesis of thiazolidin derivatives and related structures, see: Shahwar et al. (2009a ,b , 2010 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₀H₉NOS₂
M_r = 223.30
Monoclinic, P 2₁ /c
a = 13.3271 (4) Å
b = 5.9025 (2) Å
c = 13.0396 (4) Å
β = 92.812 (1)°
V = 1024.50 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 296 K
0.25 × 0.20 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.939, T_max = 0.950
7899 measured reflections
1818 independent reflections
1594 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.079
S = 1.07
1818 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.93	2.47	3.338 (2)	156
C3—H3⋯Cgⁱⁱ	0.93	2.95	3.674 (2)	136
C9—H9a⋯Cgⁱⁱⁱ	0.97	2.66	3.588 (2)	160
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810051548/dn2634sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051548/dn2634Isup2.hkl

checkCIF report

Comment top

The work presented is part of our interest in synthesizing various thiazolidin derivatives and confirming their structures by x-ray analysis (Shahwar et al., 2010, 2009a,b). These compounds will be utilized for the study of comparative bioactivity.

In (I), the benzyl moiety A (C1—C7) and the five membered ring B (N1/C8/S2/C9/C10) of 2-thioxo-1,3-thiazolidin-4-one are planar with r. m. s. deviations of 0.0157 and 0.0302 Å, respectively. The dihedral angle between A/B is 77.25 (4)° (Fig. 1). In the 2-thioxo-1,3-thiazolidin-4-one, the attached O and S-atom are at a distance of -0.1070 (25) and 0.0763 (24) Å, respectively from the mean square plane of B.

Polymeric chains [C(6), Bernstein et al. (1995)] are formed due to C—H···O hydrogen bonds (Table 1, Fig. 2) and extend along the crystallographic c axis. C—H···π interactions (Table 1) link the chains to build up a three dimensional network.

Related literature top

For background to our interest in the sythesis of thiazolidin derivatives and related structures, see: Shahwar et al. (2009a,b, 2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

The title compound has been prepared according to the method described (Shahwar et al. 2009a,b)

Structure description top

For background to our interest in the sythesis of thiazolidin derivatives and related structures, see: Shahwar et al. (2009a,b, 2010). For graph-set notation, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. Thermal ellipsoids are drawn at the 30% probability level. H-atoms are represented as small circles of arbitrary radii.
	Fig. 2. Partial packing showing the formation of the chains through C-H···O hydrogen bonds represented as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity. [Symmetry codes: (i) x, -y+3/2, z+1/2]

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

Crystal data top

C₁₀H₉NOS₂	F(000) = 464
M_r = 223.30	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1594 reflections
a = 13.3271 (4) Å	θ = 3.1–25.3°
b = 5.9025 (2) Å	µ = 0.48 mm⁻¹
c = 13.0396 (4) Å	T = 296 K
β = 92.812 (1)°	Plate, light yellow
V = 1024.50 (6) Å³	0.25 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	1818 independent reflections
Radiation source: fine-focus sealed tube	1594 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.3°, θ_min = 3.1°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→7
T_min = 0.939, T_max = 0.950	l = −15→15
7899 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.031P)² + 0.4046P] where P = (F_o² + 2F_c²)/3
1818 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₀H₉NOS₂	V = 1024.50 (6) Å³
M_r = 223.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.3271 (4) Å	µ = 0.48 mm⁻¹
b = 5.9025 (2) Å	T = 296 K
c = 13.0396 (4) Å	0.25 × 0.20 × 0.10 mm
β = 92.812 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1818 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1594 reflections with I > 2σ(I)
T_min = 0.939, T_max = 0.950	R_int = 0.023
7899 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.07	Δρ_max = 0.22 e Å⁻³
1818 reflections	Δρ_min = −0.14 e Å⁻³
127 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.06040 (4)	0.13455 (10)	0.18585 (4)	0.0638 (2)
S2	0.09221 (4)	0.28252 (9)	−0.02729 (3)	0.0557 (2)
O1	0.28194 (12)	0.7373 (2)	0.06176 (11)	0.0697 (5)
N1	0.18237 (9)	0.4684 (2)	0.12987 (9)	0.0396 (4)
C1	0.30044 (11)	0.3660 (3)	0.27679 (11)	0.0376 (5)
C2	0.33354 (12)	0.1781 (3)	0.22537 (13)	0.0443 (5)
C3	0.40774 (14)	0.0402 (3)	0.26955 (15)	0.0565 (6)
C4	0.44939 (15)	0.0897 (4)	0.36558 (16)	0.0632 (7)
C5	0.41747 (15)	0.2765 (4)	0.41688 (15)	0.0625 (7)
C6	0.34380 (14)	0.4147 (3)	0.37321 (13)	0.0509 (6)
C7	0.21689 (12)	0.5173 (3)	0.23542 (12)	0.0424 (5)
C8	0.11439 (12)	0.3010 (3)	0.10525 (13)	0.0437 (5)
C9	0.16998 (14)	0.5229 (3)	−0.05169 (13)	0.0531 (6)
C10	0.21917 (13)	0.5926 (3)	0.04939 (13)	0.0458 (5)
H2	0.30574	0.14374	0.16042	0.0531*
H3	0.42949	−0.08609	0.23425	0.0678*
H4	0.49897	−0.00340	0.39547	0.0758*
H5	0.44570	0.31047	0.48170	0.0749*
H6	0.32296	0.54169	0.40864	0.0611*
H7A	0.16040	0.50313	0.27915	0.0509*
H7B	0.23972	0.67325	0.23923	0.0509*
H9A	0.22040	0.48311	−0.09975	0.0637*
H9B	0.12960	0.64606	−0.08070	0.0637*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0582 (3)	0.0707 (4)	0.0624 (3)	−0.0218 (3)	0.0027 (2)	0.0073 (3)
S2	0.0562 (3)	0.0648 (3)	0.0451 (3)	−0.0033 (2)	−0.0074 (2)	−0.0115 (2)
O1	0.0892 (10)	0.0615 (9)	0.0584 (8)	−0.0281 (8)	0.0049 (7)	0.0054 (7)
N1	0.0425 (7)	0.0405 (7)	0.0354 (7)	−0.0013 (6)	−0.0010 (5)	−0.0012 (5)
C1	0.0404 (8)	0.0379 (8)	0.0347 (8)	−0.0064 (7)	0.0044 (6)	−0.0013 (6)
C2	0.0463 (9)	0.0459 (9)	0.0407 (9)	0.0003 (7)	0.0033 (7)	−0.0057 (7)
C3	0.0555 (10)	0.0499 (11)	0.0648 (12)	0.0086 (9)	0.0100 (9)	−0.0004 (9)
C4	0.0541 (11)	0.0672 (13)	0.0675 (13)	0.0063 (10)	−0.0052 (9)	0.0162 (11)
C5	0.0660 (12)	0.0712 (13)	0.0483 (11)	−0.0066 (10)	−0.0159 (9)	0.0056 (10)
C6	0.0612 (11)	0.0503 (10)	0.0407 (9)	−0.0039 (8)	−0.0029 (8)	−0.0065 (8)
C7	0.0502 (9)	0.0407 (9)	0.0363 (8)	0.0017 (7)	0.0020 (7)	−0.0064 (7)
C8	0.0395 (8)	0.0464 (9)	0.0448 (9)	0.0005 (7)	−0.0018 (7)	−0.0047 (7)
C9	0.0587 (10)	0.0617 (12)	0.0387 (9)	0.0052 (9)	0.0020 (8)	0.0030 (8)
C10	0.0516 (9)	0.0426 (9)	0.0433 (9)	0.0018 (8)	0.0035 (7)	0.0014 (7)

Geometric parameters (Å, º) top

S1—C8	1.6315 (18)	C4—C5	1.368 (3)
S2—C8	1.7424 (17)	C5—C6	1.378 (3)
S2—C9	1.7947 (19)	C9—C10	1.501 (2)
O1—C10	1.201 (2)	C2—H2	0.9300
N1—C7	1.459 (2)	C3—H3	0.9300
N1—C8	1.368 (2)	C4—H4	0.9300
N1—C10	1.389 (2)	C5—H5	0.9300
C1—C2	1.380 (2)	C6—H6	0.9300
C1—C6	1.388 (2)	C7—H7A	0.9700
C1—C7	1.507 (2)	C7—H7B	0.9700
C2—C3	1.384 (2)	C9—H9A	0.9700
C3—C4	1.376 (3)	C9—H9B	0.9700

C8—S2—C9	93.15 (8)	C1—C2—H2	120.00
C7—N1—C8	122.61 (13)	C3—C2—H2	120.00
C7—N1—C10	120.12 (13)	C2—C3—H3	120.00
C8—N1—C10	117.27 (13)	C4—C3—H3	120.00
C2—C1—C6	118.55 (15)	C3—C4—H4	120.00
C2—C1—C7	123.43 (14)	C5—C4—H4	120.00
C6—C1—C7	117.98 (15)	C4—C5—H5	120.00
C1—C2—C3	120.62 (16)	C6—C5—H5	120.00
C2—C3—C4	120.13 (18)	C1—C6—H6	120.00
C3—C4—C5	119.66 (19)	C5—C6—H6	120.00
C4—C5—C6	120.49 (18)	N1—C7—H7A	109.00
C1—C6—C5	120.55 (17)	N1—C7—H7B	109.00
N1—C7—C1	114.46 (13)	C1—C7—H7A	109.00
S1—C8—S2	122.86 (10)	C1—C7—H7B	109.00
S1—C8—N1	126.28 (13)	H7A—C7—H7B	108.00
S2—C8—N1	110.86 (12)	S2—C9—H9A	110.00
S2—C9—C10	106.99 (12)	S2—C9—H9B	110.00
O1—C10—N1	122.91 (16)	C10—C9—H9A	110.00
O1—C10—C9	125.76 (16)	C10—C9—H9B	110.00
N1—C10—C9	111.33 (14)	H9A—C9—H9B	109.00

C9—S2—C8—S1	176.53 (12)	C6—C1—C2—C3	0.6 (2)
C9—S2—C8—N1	−4.19 (13)	C7—C1—C2—C3	−177.17 (16)
C8—S2—C9—C10	5.77 (13)	C2—C1—C6—C5	−0.7 (3)
C8—N1—C7—C1	82.66 (18)	C7—C1—C6—C5	177.15 (17)
C10—N1—C7—C1	−96.82 (17)	C2—C1—C7—N1	−8.0 (2)
C7—N1—C8—S1	0.9 (2)	C6—C1—C7—N1	174.18 (14)
C7—N1—C8—S2	−178.35 (11)	C1—C2—C3—C4	−0.1 (3)
C10—N1—C8—S1	−179.60 (13)	C2—C3—C4—C5	−0.4 (3)
C10—N1—C8—S2	1.15 (18)	C3—C4—C5—C6	0.2 (3)
C7—N1—C10—O1	2.5 (2)	C4—C5—C6—C1	0.4 (3)
C7—N1—C10—C9	−177.06 (14)	S2—C9—C10—O1	174.34 (16)
C8—N1—C10—O1	−177.01 (16)	S2—C9—C10—N1	−6.12 (17)
C8—N1—C10—C9	3.4 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.47	3.338 (2)	156
C3—H3···Cgⁱⁱ	0.93	2.95	3.674 (2)	136
C9—H9a···Cgⁱⁱⁱ	0.97	2.66	3.588 (2)	160

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₉NOS₂
M_r	223.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.3271 (4), 5.9025 (2), 13.0396 (4)
β (°)	92.812 (1)
V (Å³)	1024.50 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.25 × 0.20 × 0.10

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.939, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	7899, 1818, 1594
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.079, 1.07
No. of reflections	1818
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.14

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.47	3.338 (2)	156
C3—H3···Cgⁱⁱ	0.93	2.95	3.674 (2)	136
C9—H9a···Cgⁱⁱⁱ	0.97	2.66	3.588 (2)	160

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2.

Acknowledgements

DS is grateful to the Higher Education Commission (Pakistan) for funding of this project and to Professor Dr Islam Ullah Khan for providing research facilities at Government College University, Lahore, Pakistan.

References

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Volume 67| Part 1| January 2011| Page o133

https://doi.org/10.1107/S1600536810051548

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