3-(4-Methyl­phen­yl)-2-thioxo-1,3-thia­zolidin-4-one

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

doi:10.1107/S1600536810029569

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2159

https://doi.org/10.1107/S1600536810029569

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3-(4-Methylphenyl)-2-thioxo-1,3-thiazolidin-4-one

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

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

(Received 19 July 2010; accepted 25 July 2010; online 31 July 2010)

In the title compound, C₁₀H₉NOS₂, the toluene group and the 2-thioxo-1,3-thiazolidin-4-one unit are planar with r.m.s. deviations of 0.0082 and 0.0136 Å, respectively. The dihedral angle between them is 71.20 (9)°. In the crystal, the molecules are stabilized through intermolecular C—H⋯O contacts, forming polymeric sheets extending parallel to the (0 $[\overline{1}]$ 1) plane. C—H⋯π contacts also occur.

Related literature

For related structures and the preparation, see: Shahwar et al. (2009a ,b ).

Experimental

Crystal data

C₁₀H₉NOS₂
M_r = 223.30
Monoclinic, P 2₁ /c
a = 14.5885 (18) Å
b = 5.5766 (6) Å
c = 12.9910 (15) Å
β = 100.603 (6)°
V = 1038.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.939, T_max = 0.950
7426 measured reflections
1871 independent reflections
1371 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.191
S = 1.07
1871 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.93	2.45	3.360 (5)	167
C5—H5⋯O1ⁱⁱ	0.93	2.51	3.432 (5)	169
C9—H9B⋯Cg2ⁱⁱⁱ	0.97	2.71	3.565 (4)	147
Symmetry codes: (i) x, y-1, z; (ii) $[x, -y+{\script{5\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536810029569/si2279sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810029569/si2279Isup2.hkl

checkCIF report

Comment top

In continuation to synthesize various derivatives of 2-thioxo-1,3-thiazolidin-4-one, the title compound (I, Fig. 1) is being reported.

The crystal structure of (II) 3-(2-methylphenyl)-2-thioxo-1,3-thiazolidin-4-one (Shahwar et al., 2009a) and (III) 3-(3-methylphenyl)-2-thioxo-1,3-thiazolidin-4-one (Shahwar et al., 2009b) have been published which differ from (I) due to the position of methyl group.

In (I), the toluene group A (C1—C7) and group B (N1/C8—C10/S1/S2/O1) of 2-thioxo-1,3-thiazolidin-4-one moiety are planar with maximum r. m. s. deviations of 0.0082 and 0.0136 Å, respectively. The dihedral angle between A/B is 71.20 (9)°. This value is different from 84.44 (9)° and 83.30 (3)° as observed in (II) and (III), respectively. The molecules are stabilized in the form polymeric sheets due to C—H···O type of intermolecular H-bondings and C—H···π contacts (Table 1). The polymeric sheets extend parallel to the (0 1 1) plane (Fig. 2).

Related literature top

For related structures and the preparation, see: Shahwar et al. (2009a,b).

Experimental top

The title compound has been prepared by the method described in (Shahwar et al., 2009a) and (Shahwar et al., 2009b).

Structure description top

In continuation to synthesize various derivatives of 2-thioxo-1,3-thiazolidin-4-one, the title compound (I, Fig. 1) is being reported.

For related structures and the preparation, see: Shahwar et al. (2009a,b).

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. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form polymeric sheets extending parallel to (0 1 1).

3-(4-Methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one top

Crystal data top

C₁₀H₉NOS₂	F(000) = 464
M_r = 223.30	D_x = 1.428 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1371 reflections
a = 14.5885 (18) Å	θ = 3.3–25.2°
b = 5.5766 (6) Å	µ = 0.48 mm⁻¹
c = 12.9910 (15) Å	T = 296 K
β = 100.603 (6)°	Prism, light yellow
V = 1038.8 (2) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	1871 independent reflections
Radiation source: fine-focus sealed tube	1371 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.2°, θ_min = 3.2°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→6
T_min = 0.939, T_max = 0.950	l = −14→15
7426 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.191	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1099P)² + 0.6595P] where P = (F_o² + 2F_c²)/3
1871 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₀H₉NOS₂	V = 1038.8 (2) Å³
M_r = 223.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.5885 (18) Å	µ = 0.48 mm⁻¹
b = 5.5766 (6) Å	T = 296 K
c = 12.9910 (15) Å	0.30 × 0.20 × 0.20 mm
β = 100.603 (6)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1871 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1371 reflections with I > 2σ(I)
T_min = 0.939, T_max = 0.950	R_int = 0.051
7426 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.191	H-atom parameters constrained
S = 1.07	Δρ_max = 0.45 e Å⁻³
1871 reflections	Δρ_min = −0.31 e Å⁻³
128 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	0.07809 (7)	0.7565 (2)	0.48054 (8)	0.0640 (4)
S2	0.08797 (7)	0.4645 (2)	0.29429 (9)	0.0645 (4)
O1	0.29145 (18)	1.1330 (5)	0.45318 (19)	0.0576 (9)
N1	0.20548 (18)	0.8215 (5)	0.3708 (2)	0.0419 (8)
C1	0.2640 (2)	0.7927 (6)	0.2936 (2)	0.0422 (10)
C2	0.3229 (2)	0.5995 (7)	0.2997 (3)	0.0486 (11)
C3	0.3830 (3)	0.5829 (7)	0.2290 (3)	0.0559 (12)
C4	0.3849 (3)	0.7554 (7)	0.1539 (3)	0.0522 (11)
C5	0.3251 (3)	0.9453 (8)	0.1489 (3)	0.0638 (14)
C6	0.2640 (3)	0.9667 (7)	0.2192 (3)	0.0561 (14)
C7	0.4528 (3)	0.7357 (9)	0.0792 (3)	0.0774 (18)
C8	0.2270 (2)	0.9984 (6)	0.4471 (3)	0.0455 (11)
C9	0.1587 (3)	0.9972 (8)	0.5211 (3)	0.0559 (12)
C10	0.1289 (2)	0.6787 (6)	0.3748 (3)	0.0470 (11)
H2	0.32242	0.48179	0.35029	0.0584*
H3	0.42296	0.45210	0.23248	0.0672*
H5	0.32517	1.06212	0.09782	0.0767*
H6	0.22378	1.09710	0.21555	0.0676*
H7A	0.48304	0.88736	0.07508	0.1162*
H7B	0.41973	0.69135	0.01101	0.1162*
H7C	0.49876	0.61574	0.10415	0.1162*
H9A	0.12591	1.14909	0.51789	0.0672*
H9B	0.19110	0.97175	0.59244	0.0672*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0506 (6)	0.0820 (8)	0.0656 (7)	−0.0038 (5)	0.0268 (5)	−0.0086 (5)
S2	0.0524 (6)	0.0690 (8)	0.0715 (8)	−0.0092 (5)	0.0097 (5)	−0.0155 (5)
O1	0.0639 (16)	0.0610 (17)	0.0485 (15)	−0.0104 (14)	0.0122 (12)	−0.0037 (12)
N1	0.0403 (14)	0.0497 (16)	0.0369 (14)	0.0036 (12)	0.0106 (11)	−0.0002 (12)
C1	0.0431 (18)	0.050 (2)	0.0345 (16)	0.0003 (14)	0.0098 (13)	−0.0013 (14)
C2	0.051 (2)	0.052 (2)	0.0429 (19)	0.0044 (16)	0.0093 (15)	0.0068 (16)
C3	0.051 (2)	0.066 (2)	0.052 (2)	0.0110 (18)	0.0132 (16)	−0.0024 (19)
C4	0.049 (2)	0.070 (2)	0.0395 (18)	−0.0142 (18)	0.0133 (15)	−0.0076 (17)
C5	0.089 (3)	0.063 (2)	0.044 (2)	−0.003 (2)	0.024 (2)	0.0133 (18)
C6	0.075 (3)	0.049 (2)	0.047 (2)	0.0102 (18)	0.0185 (18)	0.0057 (17)
C7	0.060 (3)	0.123 (4)	0.055 (2)	−0.022 (2)	0.026 (2)	−0.019 (2)
C8	0.052 (2)	0.0459 (19)	0.0391 (18)	0.0040 (16)	0.0099 (15)	0.0013 (14)
C9	0.056 (2)	0.069 (2)	0.045 (2)	0.0045 (18)	0.0150 (16)	−0.0037 (17)
C10	0.0400 (18)	0.053 (2)	0.048 (2)	0.0015 (15)	0.0080 (14)	0.0010 (15)

Geometric parameters (Å, º) top

S1—C9	1.798 (5)	C4—C7	1.513 (6)
S1—C10	1.732 (4)	C5—C6	1.394 (6)
S2—C10	1.627 (4)	C8—C9	1.507 (5)
O1—C8	1.194 (4)	C2—H2	0.9300
N1—C1	1.441 (4)	C3—H3	0.9300
N1—C8	1.393 (4)	C5—H5	0.9300
N1—C10	1.381 (4)	C6—H6	0.9300
C1—C2	1.371 (5)	C7—H7A	0.9600
C1—C6	1.370 (5)	C7—H7B	0.9600
C2—C3	1.385 (5)	C7—H7C	0.9600
C3—C4	1.374 (5)	C9—H9A	0.9700
C4—C5	1.366 (6)	C9—H9B	0.9700

S1···N1	2.568 (3)	C6···H9B^vii	3.0300
S1···S1ⁱ	3.7490 (16)	C7···H3^viii	3.0200
S1···S1ⁱⁱ	3.6396 (16)	C8···H6	3.0500
S2···C2	3.497 (3)	C8···H7B^v	2.9800
S2···C8ⁱⁱⁱ	3.651 (4)	C10···H2	3.1000
S1···H9Aⁱⁱ	3.0300	H2···O1ⁱⁱⁱ	2.4500
S2···H6ⁱⁱⁱ	3.1500	H2···C10	3.1000
O1···C2^iv	3.360 (5)	H3···H7C	2.3500
O1···C6	3.132 (5)	H3···C7^ix	3.0200
O1···C7^v	3.321 (5)	H5···H7A	2.5700
O1···H2^iv	2.4500	H5···O1^x	2.5100
O1···H5^vi	2.5100	H6···S2^iv	3.1500
O1···H7B^v	2.6100	H6···C8	3.0500
N1···S1	2.568 (3)	H7A···H5	2.5700
C2···S2	3.497 (3)	H7A···H7A^xi	2.4500
C2···O1ⁱⁱⁱ	3.360 (5)	H7B···O1^vii	2.6100
C4···C8^vii	3.500 (5)	H7B···C2^vii	3.0800
C6···O1	3.132 (5)	H7B···C8^vii	2.9800
C7···O1^vii	3.321 (5)	H7C···H3	2.3500
C8···S2^iv	3.651 (4)	H9A···S1ⁱⁱ	3.0300
C8···C4^v	3.500 (5)	H9B···C1^v	3.0200
C1···H9B^vii	3.0200	H9B···C2^v	3.0300
C2···H9B^vii	3.0300	H9B···C3^v	3.0400
C2···H7B^v	3.0800	H9B···C4^v	3.0700
C3···H9B^vii	3.0400	H9B···C5^v	3.0400
C4···H9B^vii	3.0700	H9B···C6^v	3.0300
C5···H9B^vii	3.0400

C9—S1—C10	93.85 (18)	S2—C10—N1	127.1 (3)
C1—N1—C8	119.3 (3)	C1—C2—H2	121.00
C1—N1—C10	123.3 (3)	C3—C2—H2	121.00
C8—N1—C10	117.4 (3)	C2—C3—H3	119.00
N1—C1—C2	119.5 (3)	C4—C3—H3	119.00
N1—C1—C6	119.3 (3)	C4—C5—H5	120.00
C2—C1—C6	121.1 (3)	C6—C5—H5	119.00
C1—C2—C3	118.7 (3)	C1—C6—H6	121.00
C2—C3—C4	121.5 (4)	C5—C6—H6	120.00
C3—C4—C5	118.7 (4)	C4—C7—H7A	109.00
C3—C4—C7	120.4 (4)	C4—C7—H7B	109.00
C5—C4—C7	120.9 (4)	C4—C7—H7C	109.00
C4—C5—C6	121.0 (4)	H7A—C7—H7B	109.00
C1—C6—C5	119.0 (4)	H7A—C7—H7C	109.00
O1—C8—N1	124.3 (3)	H7B—C7—H7C	109.00
O1—C8—C9	124.5 (3)	S1—C9—H9A	110.00
N1—C8—C9	111.2 (3)	S1—C9—H9B	110.00
S1—C9—C8	106.9 (3)	C8—C9—H9A	110.00
S1—C10—S2	122.26 (19)	C8—C9—H9B	110.00
S1—C10—N1	110.7 (2)	H9A—C9—H9B	109.00

C9—S1—C10—N1	1.8 (3)	C10—N1—C8—C9	−0.3 (4)
C10—S1—C9—C8	−1.9 (3)	N1—C1—C6—C5	176.0 (3)
C9—S1—C10—S2	−178.1 (3)	C6—C1—C2—C3	0.1 (5)
C10—N1—C1—C2	−72.1 (4)	N1—C1—C2—C3	−175.8 (3)
C8—N1—C10—S2	178.7 (3)	C2—C1—C6—C5	0.0 (5)
C8—N1—C1—C6	−69.3 (4)	C1—C2—C3—C4	0.3 (6)
C10—N1—C1—C6	111.9 (4)	C2—C3—C4—C7	178.6 (4)
C8—N1—C1—C2	106.7 (4)	C2—C3—C4—C5	−0.7 (6)
C1—N1—C10—S1	177.6 (2)	C3—C4—C5—C6	0.9 (6)
C8—N1—C10—S1	−1.2 (4)	C7—C4—C5—C6	−178.5 (4)
C1—N1—C10—S2	−2.5 (5)	C4—C5—C6—C1	−0.5 (6)
C1—N1—C8—O1	0.7 (5)	O1—C8—C9—S1	−178.3 (3)
C10—N1—C8—O1	179.5 (3)	N1—C8—C9—S1	1.5 (4)
C1—N1—C8—C9	−179.1 (3)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) x, y−1, z; (iv) x, y+1, z; (v) x, −y+3/2, z+1/2; (vi) x, −y+5/2, z+1/2; (vii) x, −y+3/2, z−1/2; (viii) −x+1, y+1/2, −z+1/2; (ix) −x+1, y−1/2, −z+1/2; (x) x, −y+5/2, z−1/2; (xi) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱⁱⁱ	0.93	2.45	3.360 (5)	167
C5—H5···O1^x	0.93	2.51	3.432 (5)	169
C9—H9B···Cg2^v	0.97	2.71	3.565 (4)	147

Symmetry codes: (iii) x, y−1, z; (v) x, −y+3/2, z+1/2; (x) x, −y+5/2, 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)	14.5885 (18), 5.5766 (6), 12.9910 (15)
β (°)	100.603 (6)
V (Å³)	1038.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.30 × 0.20 × 0.20

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	7426, 1871, 1371
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.191, 1.07
No. of reflections	1871
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.31

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

Cg2 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.45	3.360 (5)	167
C5—H5···O1ⁱⁱ	0.93	2.51	3.432 (5)	169
C9—H9B···Cg2ⁱⁱⁱ	0.97	2.71	3.565 (4)	147

Symmetry codes: (i) x, y−1, z; (ii) x, −y+5/2, z−1/2; (iii) x, −y+3/2, z+1/2.

Acknowledgements

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

References

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2159

https://doi.org/10.1107/S1600536810029569

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