3-Butyl-2-phenyl-1,3-thia­zolidine-1,4-dione

Wang, Q.; Xu, Z.; Sun, Y.

doi:10.1107/S1600536810018003

organic compounds

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Volume 66| Part 6| June 2010| Page o1422

https://doi.org/10.1107/S1600536810018003

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3-Butyl-2-phenyl-1,3-thiazolidine-1,4-dione

Qiang Wang,^a ^* Zhouqin Xu ^a and Yanchun Sun ^b

^aDepartment of Physics–Chemistry, Henan Polytechnic University, Jiao Zuo 454000, People's Republic of China, and ^bDepartment of Medicine, Hebi College of Vocation and Technology, He Bi 458030, People's Republic of China
^*Correspondence e-mail: wangqiang@hpu.edu.cn

(Received 1 May 2010; accepted 15 May 2010; online 22 May 2010)

In the title compound, C₁₃H₁₇NO₂S, the thiazolidine-1,4-dione ring adopts an envelope conformation with the S atom lying 0.631 (4) Å out of the plane formed by the other four ring atoms; the phenyl ring is almost perpendicular [88.74 (8)°] with respect to the ring C—C—N—C atoms and the butyl chain is in a fully extended conformation. In the crystal, a supramolecular two-dimensional arrangement arises from weak intermolecular C—H⋯O interactions.

Related literature

For related structures, see: Wang et al. (2009 ); Xu et al. (2009 ). For synthetic procedures, see: Johnson et al. (1983 ); Srivastava et al. (2002 ).

Experimental

Crystal data

C₁₃H₁₇NO₂S
M_r = 251.34
Monoclinic, P 2₁ /c
a = 13.8335 (5) Å
b = 8.7461 (3) Å
c = 12.3853 (4) Å
β = 114.773 (2)°
V = 1360.59 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 297 K
0.28 × 0.26 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.939, T_max = 0.956
15990 measured reflections
3118 independent reflections
2169 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.159
S = 1.14
3118 reflections
155 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O1ⁱ	0.97	2.43	3.246 (3)	142
C3—H3⋯O2ⁱⁱ	0.98	2.34	3.311 (3)	172
C11—H11B⋯O2ⁱⁱ	0.97	2.59	3.548 (4)	169
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2001 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810018003/pv2278sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810018003/pv2278Isup2.hkl

checkCIF report

Comment top

As a part of our programme studying the new applications of cyclic sulfoxide derivatives in medicne (Wang, et al., 2009; Xu, et al., 2009), we report herein the crystal structure of the title compounds.

The molecular structure of the title compound is shown in Fig. 1. The thiazolidin-4-one ring adopts an envelope conformation with S lying 0.631 (4) Å out of the plane formed by the rest of the ring atoms; the phenyl ring is oriented at right angles (88.74 (8)°) with respect to the ring (C2/C3/N1/C1) atoms. The butyl chain is in a fully extended conformation. The crystal packing (Fig. 2) consists of a two-dimensional network in the a-c-plane generated by intermolecular interactions of the weak C—H···O hydrogen bonds.

Related literature top

For related structures, see: Wang et al. (2009); Xu et al. (2009). For synthetic procedures, see: Johnson et al. (1983); Srivastava et al. (2002);

Experimental top

All reagents were of analytical grade. The title compound was prepared according to literature methods (Srivastava et al., 2002; Johnson et al., 1983). It was characterized by recording its infrared spectra and elemental analyses. Single crystals of the title compound were obtained by slow evaporation of its chloroform solution at room temperature.

Structure description top

For related structures, see: Wang et al. (2009); Xu et al. (2009). For synthetic procedures, see: Johnson et al. (1983); Srivastava et al. (2002);

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the unit cell packing of the title compound down the a-axis showing hydrogen bonds as dashed lines.

3-Butyl-2-phenyl-1,3-thiazolidine-1,4-dione top

Crystal data top

C₁₃H₁₇NO₂S	F(000) = 536
M_r = 251.34	D_x = 1.227 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5947 reflections
a = 13.8335 (5) Å	θ = 2.8–25.9°
b = 8.7461 (3) Å	µ = 0.23 mm⁻¹
c = 12.3853 (4) Å	T = 297 K
β = 114.773 (2)°	Block, yellow
V = 1360.59 (8) Å³	0.28 × 0.26 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3118 independent reflections
Radiation source: fine-focus sealed tube	2169 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
φ and ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −17→12
T_min = 0.939, T_max = 0.956	k = −11→11
15990 measured reflections	l = −15→16

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0833P)² + 0.1042P] where P = (F_o² + 2F_c²)/3
3118 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.34 e Å⁻³
6 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₃H₁₇NO₂S	V = 1360.59 (8) Å³
M_r = 251.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.8335 (5) Å	µ = 0.23 mm⁻¹
b = 8.7461 (3) Å	T = 297 K
c = 12.3853 (4) Å	0.28 × 0.26 × 0.20 mm
β = 114.773 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3118 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	2169 reflections with I > 2σ(I)
T_min = 0.939, T_max = 0.956	R_int = 0.030
15990 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	6 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.14	Δρ_max = 0.34 e Å⁻³
3118 reflections	Δρ_min = −0.29 e Å⁻³
155 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 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
N1	0.25227 (13)	0.66161 (18)	0.36775 (14)	0.0437 (4)
O1	0.04410 (14)	0.84045 (17)	0.19284 (19)	0.0788 (6)
O2	0.24851 (16)	0.7278 (2)	0.54296 (16)	0.0820 (6)
S1	0.04960 (4)	0.67497 (6)	0.22013 (5)	0.0522 (2)
C1	0.20313 (18)	0.6887 (2)	0.4393 (2)	0.0514 (5)
C2	0.08545 (18)	0.6614 (2)	0.3755 (2)	0.0553 (6)
H2A	0.0469	0.7371	0.3993	0.066*
H2B	0.0678	0.5608	0.3949	0.066*
C3	0.18626 (14)	0.6127 (2)	0.24789 (16)	0.0410 (5)
H3	0.2085	0.6679	0.1933	0.049*
C4	0.18891 (14)	0.4445 (2)	0.22558 (16)	0.0393 (4)
C5	0.15706 (17)	0.3929 (2)	0.10953 (19)	0.0525 (5)
H5	0.1360	0.4631	0.0474	0.063*
C6	0.1564 (2)	0.2395 (3)	0.0856 (2)	0.0650 (7)
H6	0.1346	0.2067	0.0075	0.078*
C7	0.1875 (2)	0.1350 (3)	0.1756 (3)	0.0692 (7)
H7	0.1875	0.0313	0.1589	0.083*
C8	0.2186 (2)	0.1831 (3)	0.2906 (3)	0.0677 (7)
H8	0.2387	0.1118	0.3518	0.081*
C9	0.22036 (17)	0.3375 (2)	0.3161 (2)	0.0531 (6)
H9	0.2428	0.3694	0.3945	0.064*
C10	0.36729 (17)	0.6710 (3)	0.4092 (2)	0.0577 (6)
H10A	0.3932	0.5761	0.3906	0.069*
H10B	0.3996	0.6830	0.4949	0.069*
C11	0.4012 (2)	0.8007 (3)	0.3546 (3)	0.0734 (7)
H11A	0.3744	0.8954	0.3726	0.088*
H11B	0.3689	0.7882	0.2689	0.088*
C12	0.5200 (2)	0.8135 (4)	0.3968 (3)	0.1025 (11)
H12A	0.5521	0.8311	0.4820	0.123*
H12B	0.5473	0.7173	0.3821	0.123*
C13	0.5527 (3)	0.9381 (6)	0.3380 (4)	0.1532 (17)
H13A	0.5328	0.9122	0.2561	0.184*
H13B	0.6284	0.9516	0.3773	0.184*
H13C	0.5179	1.0314	0.3425	0.184*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0431 (9)	0.0507 (10)	0.0389 (9)	−0.0063 (7)	0.0189 (7)	−0.0076 (7)
O1	0.0751 (12)	0.0415 (10)	0.1114 (15)	0.0132 (7)	0.0307 (11)	0.0173 (9)
O2	0.0877 (14)	0.1101 (16)	0.0556 (11)	−0.0193 (11)	0.0372 (10)	−0.0332 (10)
S1	0.0453 (3)	0.0400 (3)	0.0641 (4)	0.0035 (2)	0.0156 (3)	0.0018 (2)
C1	0.0614 (14)	0.0500 (12)	0.0506 (14)	−0.0080 (10)	0.0312 (11)	−0.0118 (10)
C2	0.0566 (13)	0.0484 (12)	0.0733 (16)	−0.0076 (9)	0.0395 (12)	−0.0104 (10)
C3	0.0437 (10)	0.0447 (10)	0.0367 (11)	−0.0019 (8)	0.0190 (9)	0.0008 (8)
C4	0.0381 (10)	0.0426 (10)	0.0403 (11)	0.0019 (8)	0.0195 (8)	−0.0010 (8)
C5	0.0572 (13)	0.0567 (13)	0.0464 (13)	0.0022 (10)	0.0243 (10)	−0.0042 (10)
C6	0.0661 (16)	0.0669 (16)	0.0636 (16)	−0.0004 (12)	0.0288 (13)	−0.0227 (13)
C7	0.0654 (15)	0.0489 (13)	0.094 (2)	0.0026 (11)	0.0339 (15)	−0.0165 (14)
C8	0.0723 (17)	0.0492 (14)	0.083 (2)	0.0130 (11)	0.0336 (14)	0.0151 (12)
C9	0.0617 (14)	0.0517 (12)	0.0472 (13)	0.0068 (10)	0.0241 (11)	0.0037 (9)
C10	0.0464 (12)	0.0706 (15)	0.0527 (14)	−0.0020 (10)	0.0174 (10)	−0.0063 (11)
C11	0.0514 (15)	0.0891 (18)	0.0734 (18)	−0.0103 (13)	0.0200 (13)	0.0048 (14)
C12	0.0567 (17)	0.137 (3)	0.113 (3)	−0.0209 (17)	0.0347 (18)	−0.005 (2)
C13	0.127 (2)	0.179 (3)	0.168 (3)	−0.041 (2)	0.076 (2)	0.009 (2)

Geometric parameters (Å, º) top

N1—C1	1.345 (2)	C7—C8	1.370 (4)
N1—C3	1.444 (2)	C7—H7	0.9300
N1—C10	1.455 (3)	C8—C9	1.385 (3)
O1—S1	1.4809 (16)	C8—H8	0.9300
O2—C1	1.218 (3)	C9—H9	0.9300
S1—C2	1.779 (2)	C10—C11	1.493 (3)
S1—C3	1.8559 (18)	C10—H10A	0.9700
C1—C2	1.501 (3)	C10—H10B	0.9700
C2—H2A	0.9700	C11—C12	1.507 (4)
C2—H2B	0.9700	C11—H11A	0.9700
C3—C4	1.500 (3)	C11—H11B	0.9700
C3—H3	0.9800	C12—C13	1.482 (5)
C4—C9	1.383 (3)	C12—H12A	0.9700
C4—C5	1.390 (3)	C12—H12B	0.9700
C5—C6	1.374 (3)	C13—H13A	0.9600
C5—H5	0.9300	C13—H13B	0.9600
C6—C7	1.364 (4)	C13—H13C	0.9600
C6—H6	0.9300

C1—N1—C3	116.95 (17)	C8—C7—H7	120.1
C1—N1—C10	122.52 (18)	C7—C8—C9	120.3 (2)
C3—N1—C10	120.42 (15)	C7—C8—H8	119.8
O1—S1—C2	106.05 (11)	C9—C8—H8	119.8
O1—S1—C3	106.27 (10)	C8—C9—C4	120.3 (2)
C2—S1—C3	88.82 (9)	C8—C9—H9	119.8
O2—C1—N1	124.4 (2)	C4—C9—H9	119.8
O2—C1—C2	124.46 (19)	N1—C10—C11	112.81 (18)
N1—C1—C2	111.17 (19)	N1—C10—H10A	109.0
C1—C2—S1	107.95 (14)	C11—C10—H10A	109.0
C1—C2—H2A	110.1	N1—C10—H10B	109.0
S1—C2—H2A	110.1	C11—C10—H10B	109.0
C1—C2—H2B	110.1	H10A—C10—H10B	107.8
S1—C2—H2B	110.1	C10—C11—C12	113.8 (2)
H2A—C2—H2B	108.4	C10—C11—H11A	108.8
N1—C3—C4	115.24 (16)	C12—C11—H11A	108.8
N1—C3—S1	105.05 (12)	C10—C11—H11B	108.8
C4—C3—S1	110.82 (12)	C12—C11—H11B	108.8
N1—C3—H3	108.5	H11A—C11—H11B	107.7
C4—C3—H3	108.5	C13—C12—C11	113.4 (3)
S1—C3—H3	108.5	C13—C12—H12A	108.9
C9—C4—C5	118.34 (19)	C11—C12—H12A	108.9
C9—C4—C3	122.52 (18)	C13—C12—H12B	108.9
C5—C4—C3	119.13 (17)	C11—C12—H12B	108.9
C6—C5—C4	120.7 (2)	H12A—C12—H12B	107.7
C6—C5—H5	119.6	C12—C13—H13A	109.5
C4—C5—H5	119.6	C12—C13—H13B	109.5
C7—C6—C5	120.5 (2)	H13A—C13—H13B	109.5
C7—C6—H6	119.8	C12—C13—H13C	109.5
C5—C6—H6	119.8	H13A—C13—H13C	109.5
C6—C7—C8	119.8 (2)	H13B—C13—H13C	109.5
C6—C7—H7	120.1

C3—N1—C1—O2	178.6 (2)	N1—C3—C4—C9	21.3 (3)
C10—N1—C1—O2	2.4 (3)	S1—C3—C4—C9	−97.9 (2)
C3—N1—C1—C2	−0.3 (2)	N1—C3—C4—C5	−159.80 (16)
C10—N1—C1—C2	−176.47 (18)	S1—C3—C4—C5	81.10 (18)
O2—C1—C2—S1	159.4 (2)	C9—C4—C5—C6	0.3 (3)
N1—C1—C2—S1	−21.8 (2)	C3—C4—C5—C6	−178.67 (18)
O1—S1—C2—C1	−78.65 (16)	C4—C5—C6—C7	−0.2 (3)
C3—S1—C2—C1	27.94 (15)	C5—C6—C7—C8	0.6 (4)
C1—N1—C3—C4	−101.4 (2)	C6—C7—C8—C9	−1.0 (4)
C10—N1—C3—C4	74.9 (2)	C7—C8—C9—C4	1.1 (3)
C1—N1—C3—S1	20.9 (2)	C5—C4—C9—C8	−0.7 (3)
C10—N1—C3—S1	−162.82 (15)	C3—C4—C9—C8	178.21 (18)
O1—S1—C3—N1	78.93 (14)	C1—N1—C10—C11	−112.5 (2)
C2—S1—C3—N1	−27.45 (13)	C3—N1—C10—C11	71.4 (2)
O1—S1—C3—C4	−155.99 (14)	N1—C10—C11—C12	179.6 (2)
C2—S1—C3—C4	97.63 (14)	C10—C11—C12—C13	177.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O1ⁱ	0.97	2.43	3.246 (3)	142
C3—H3···O2ⁱⁱ	0.98	2.34	3.311 (3)	172
C9—H9···N1	0.93	2.59	2.899 (2)	100
C10—H10B···O2	0.97	2.43	2.824 (3)	104
C11—H11B···O2ⁱⁱ	0.97	2.59	3.548 (4)	169

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₇NO₂S
M_r	251.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	297
a, b, c (Å)	13.8335 (5), 8.7461 (3), 12.3853 (4)
β (°)	114.773 (2)
V (Å³)	1360.59 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.28 × 0.26 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.939, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	15990, 3118, 2169
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.159, 1.14
No. of reflections	3118
No. of parameters	155
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.29

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O1ⁱ	0.97	2.43	3.246 (3)	142
C3—H3···O2ⁱⁱ	0.98	2.34	3.311 (3)	172
C11—H11B···O2ⁱⁱ	0.97	2.59	3.548 (4)	169

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

Acknowledgements

This work was supported by the Foundation of Henan Polytechnic University for Doctor Teachers (B2010-65), and the authors thank Dr L. Yang, Dr D. Zhao and Dr Z. Z. Zhang for their support of the data collection and analysis.

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