3-Butyl-2-phenyl-1,3-thia-zolidine-1,4-dione.

In the title compound, C(13)H(17)NO(2)S, the thia-zolidine-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 supra-molecular two-dimensional arrangement arises from weak inter-molecular C-H⋯O inter-actions.

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 = 251.34

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.159

S = 1.14

3118 reflections

155 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.29 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018003/pv2278Isup2.hkl

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

C13H17NO2S	F(000) = 536
Mr = 251.34	Dx = 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

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

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(Fo2) + (0.0833P)2 + 0.1042P] where P = (Fo2 + 2Fc2)/3
3118 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.34 e Å−3
6 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .