N-(3-Butyl-4-oxo-1,3-thia-zolidin-2-yl-idene)benzamide.

In the title compound, C(14)H(16)N(2)O(2)S, the thia-zolidine ring is planar [maximum atomic deviation = 0.0080 (14) Å] and twisted slightly with respect to the phenyl ring, making a dihedral angle of 4.46 (14)°. The butyl group displays an extended conformation, with a torsion angle of 169.4 (4)°. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules, forming supra-molecular chains.

Related literature

For the pharmaceutical applications of thia­zolidinones, see: Amin et al. (2008 ▶); Ramla et al. (2007 ▶). For the synthesis, see: Peng et al. (2004 ▶).

Experimental

Crystal data

C14H16N2O2S

M = 276.35

Monoclinic,

a = 5.4690 (1) Å

b = 30.5591 (8) Å

c = 8.6032 (2) Å

β = 99.895 (3)°

V = 1416.44 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 294 K

0.50 × 0.14 × 0.07 mm

Data collection

Oxford Diffraction Nova A diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2008 ▶) T min = 0.895, T max = 0.984

7446 measured reflections

2530 independent reflections

1987 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.129

S = 1.06

2530 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 OLEX2 (Dolomanov et al., 2009 ▶).; software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810020556/sj2789sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020556/sj2789Isup2.hkl

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

C14H16N2O2S	F(000) = 584
Mr = 276.35	Dx = 1.296 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3174 reflections
a = 5.4690 (1) Å	θ = 2.8–25.0°
b = 30.5591 (8) Å	µ = 0.23 mm−1
c = 8.6032 (2) Å	T = 294 K
β = 99.895 (3)°	Platelet, yellow
V = 1416.44 (6) Å3	0.50 × 0.14 × 0.07 mm
Z = 4

Oxford Diffraction Nova A diffractometer	2530 independent reflections
Radiation source: fine-focus sealed tube	1987 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 25.1°, θmin = 1.3°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2008)	h = −6→3
Tmin = 0.895, Tmax = 0.984	k = −36→36
7446 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.0615P)2 + 0.3856P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2530 reflections	Δρmax = 0.20 e Å−3
174 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0113 (18)

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
S1	0.28923 (11)	0.210301 (19)	0.34733 (8)	0.0680 (2)
N1	0.0399 (3)	0.14912 (6)	0.1466 (2)	0.0568 (5)
N2	0.4097 (3)	0.12988 (6)	0.3021 (2)	0.0604 (5)
O1	−0.1307 (3)	0.21815 (6)	0.1475 (2)	0.0846 (6)
O2	0.7761 (3)	0.11970 (7)	0.4680 (2)	0.0903 (6)
C1	−0.3441 (4)	0.12483 (8)	−0.0946 (3)	0.0675 (6)
H1	−0.2120	0.1058	−0.0637	0.081*
C2	−0.5428 (5)	0.11225 (10)	−0.2086 (3)	0.0834 (8)
H2	−0.5435	0.0846	−0.2540	0.100*
C3	−0.7382 (5)	0.14015 (11)	−0.2550 (3)	0.0850 (8)
H3	−0.8711	0.1313	−0.3310	0.102*
C4	−0.7377 (4)	0.18069 (11)	−0.1902 (3)	0.0798 (8)
H4	−0.8697	0.1996	−0.2228	0.096*
C5	−0.5429 (4)	0.19391 (8)	−0.0765 (3)	0.0674 (6)
H5	−0.5441	0.2217	−0.0322	0.081*
C6	−0.3447 (4)	0.16583 (7)	−0.0278 (2)	0.0555 (5)
C7	−0.1369 (4)	0.18080 (7)	0.0965 (3)	0.0588 (5)
C8	0.2273 (4)	0.16005 (7)	0.2522 (2)	0.0543 (5)
C9	0.6056 (4)	0.14333 (9)	0.4145 (3)	0.0669 (6)
C10	0.5774 (4)	0.19006 (9)	0.4582 (3)	0.0740 (7)
H10A	0.7154	0.2071	0.4338	0.089*
H10B	0.5756	0.1925	0.5704	0.089*
C11	0.4005 (4)	0.08576 (8)	0.2365 (3)	0.0693 (6)
H11A	0.5683	0.0746	0.2452	0.083*
H11B	0.3289	0.0870	0.1253	0.083*
C12	0.2517 (5)	0.05489 (9)	0.3177 (4)	0.0900 (8)
H12A	0.0871	0.0669	0.3160	0.108*
H12B	0.3303	0.0516	0.4271	0.108*
C13	0.2296 (8)	0.01017 (11)	0.2380 (6)	0.1436 (17)
H13A	0.1831	0.0146	0.1251	0.172*
H13B	0.3921	−0.0035	0.2564	0.172*
C14	0.0574 (10)	−0.01942 (15)	0.2872 (8)	0.194 (3)
H14A	0.0878	−0.0214	0.4002	0.291*
H14B	0.0767	−0.0478	0.2430	0.291*
H14C	−0.1084	−0.0091	0.2515	0.291*

	U11	U22	U33	U12	U13	U23
S1	0.0674 (4)	0.0599 (4)	0.0716 (4)	−0.0109 (3)	−0.0022 (3)	−0.0083 (3)
N1	0.0544 (10)	0.0541 (10)	0.0564 (10)	−0.0011 (8)	−0.0061 (8)	0.0013 (8)
N2	0.0529 (10)	0.0640 (11)	0.0592 (10)	0.0002 (8)	−0.0045 (8)	0.0004 (9)
O1	0.0866 (12)	0.0620 (10)	0.0931 (13)	0.0110 (8)	−0.0190 (10)	−0.0116 (9)
O2	0.0606 (10)	0.1150 (15)	0.0852 (12)	0.0086 (10)	−0.0155 (9)	0.0012 (11)
C1	0.0633 (13)	0.0679 (14)	0.0656 (14)	−0.0014 (11)	−0.0054 (11)	−0.0005 (11)
C2	0.0786 (17)	0.0852 (18)	0.0781 (17)	−0.0140 (14)	−0.0104 (13)	−0.0076 (14)
C3	0.0620 (15)	0.115 (2)	0.0689 (16)	−0.0187 (15)	−0.0132 (12)	0.0112 (16)
C4	0.0534 (13)	0.102 (2)	0.0792 (17)	0.0026 (13)	−0.0040 (12)	0.0219 (16)
C5	0.0577 (13)	0.0705 (14)	0.0714 (14)	0.0035 (11)	0.0035 (11)	0.0101 (12)
C6	0.0495 (11)	0.0596 (12)	0.0548 (11)	−0.0026 (9)	0.0021 (9)	0.0075 (10)
C7	0.0584 (12)	0.0539 (12)	0.0606 (12)	0.0001 (10)	0.0001 (10)	0.0009 (10)
C8	0.0534 (11)	0.0540 (12)	0.0531 (11)	−0.0059 (9)	0.0027 (9)	0.0013 (9)
C9	0.0506 (12)	0.0865 (17)	0.0590 (13)	−0.0085 (11)	−0.0035 (10)	0.0037 (12)
C10	0.0615 (14)	0.0884 (18)	0.0669 (14)	−0.0221 (12)	−0.0039 (11)	−0.0040 (13)
C11	0.0608 (13)	0.0674 (14)	0.0751 (15)	0.0091 (11)	−0.0013 (11)	−0.0030 (12)
C12	0.0860 (19)	0.0689 (16)	0.114 (2)	0.0021 (14)	0.0156 (17)	−0.0020 (16)
C13	0.144 (3)	0.0650 (19)	0.234 (5)	−0.012 (2)	0.068 (3)	−0.017 (3)
C14	0.179 (5)	0.108 (3)	0.313 (8)	−0.038 (3)	0.093 (5)	−0.040 (4)

S1—C8	1.746 (2)	C5—C6	1.390 (3)
S1—C10	1.805 (2)	C5—H5	0.9300
N1—C8	1.291 (3)	C6—C7	1.492 (3)
N1—C7	1.384 (3)	C9—C10	1.491 (4)
N2—C8	1.372 (3)	C10—H10A	0.9700
N2—C9	1.377 (3)	C10—H10B	0.9700
N2—C11	1.459 (3)	C11—C12	1.495 (4)
O1—C7	1.221 (3)	C11—H11A	0.9700
O2—C9	1.206 (3)	C11—H11B	0.9700
C1—C6	1.379 (3)	C12—C13	1.525 (5)
C1—C2	1.387 (3)	C12—H12A	0.9700
C1—H1	0.9300	C12—H12B	0.9700
C2—C3	1.372 (4)	C13—C14	1.421 (5)
C2—H2	0.9300	C13—H13A	0.9700
C3—C4	1.359 (4)	C13—H13B	0.9700
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.377 (3)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C8—S1—C10	91.59 (11)	N2—C9—C10	111.2 (2)
C8—N1—C7	117.76 (19)	C9—C10—S1	108.30 (15)
C8—N2—C9	117.08 (19)	C9—C10—H10A	110.0
C8—N2—C11	121.66 (17)	S1—C10—H10A	110.0
C9—N2—C11	121.24 (19)	C9—C10—H10B	110.0
C6—C1—C2	119.3 (2)	S1—C10—H10B	110.0
C6—C1—H1	120.4	H10A—C10—H10B	108.4
C2—C1—H1	120.4	N2—C11—C12	112.8 (2)
C3—C2—C1	120.7 (3)	N2—C11—H11A	109.0
C3—C2—H2	119.7	C12—C11—H11A	109.0
C1—C2—H2	119.7	N2—C11—H11B	109.0
C4—C3—C2	120.0 (2)	C12—C11—H11B	109.0
C4—C3—H3	120.0	H11A—C11—H11B	107.8
C2—C3—H3	120.0	C11—C12—C13	111.3 (3)
C3—C4—C5	120.4 (2)	C11—C12—H12A	109.4
C3—C4—H4	119.8	C13—C12—H12A	109.4
C5—C4—H4	119.8	C11—C12—H12B	109.4
C4—C5—C6	120.1 (2)	C13—C12—H12B	109.4
C4—C5—H5	120.0	H12A—C12—H12B	108.0
C6—C5—H5	120.0	C14—C13—C12	116.2 (4)
C1—C6—C5	119.5 (2)	C14—C13—H13A	108.2
C1—C6—C7	121.44 (19)	C12—C13—H13A	108.2
C5—C6—C7	119.0 (2)	C14—C13—H13B	108.2
O1—C7—N1	124.6 (2)	C12—C13—H13B	108.2
O1—C7—C6	121.0 (2)	H13A—C13—H13B	107.4
N1—C7—C6	114.46 (19)	C13—C14—H14A	109.5
N1—C8—N2	119.52 (19)	C13—C14—H14B	109.5
N1—C8—S1	128.62 (17)	H14A—C14—H14B	109.5
N2—C8—S1	111.86 (14)	C13—C14—H14C	109.5
O2—C9—N2	123.1 (2)	H14A—C14—H14C	109.5
O2—C9—C10	125.7 (2)	H14B—C14—H14C	109.5
C6—C1—C2—C3	0.1 (4)	C11—N2—C8—N1	1.3 (3)
C1—C2—C3—C4	0.5 (4)	C9—N2—C8—S1	−0.2 (3)
C2—C3—C4—C5	−0.7 (4)	C11—N2—C8—S1	−178.67 (17)
C3—C4—C5—C6	0.3 (4)	C10—S1—C8—N1	−179.2 (2)
C2—C1—C6—C5	−0.5 (4)	C10—S1—C8—N2	0.77 (18)
C2—C1—C6—C7	179.3 (2)	C8—N2—C9—O2	179.6 (2)
C4—C5—C6—C1	0.3 (4)	C11—N2—C9—O2	−1.9 (4)
C4—C5—C6—C7	−179.5 (2)	C8—N2—C9—C10	−0.7 (3)
C8—N1—C7—O1	−1.5 (4)	C11—N2—C9—C10	177.8 (2)
C8—N1—C7—C6	178.87 (18)	O2—C9—C10—S1	−179.1 (2)
C1—C6—C7—O1	175.0 (2)	N2—C9—C10—S1	1.2 (3)
C5—C6—C7—O1	−5.1 (3)	C8—S1—C10—C9	−1.12 (19)
C1—C6—C7—N1	−5.3 (3)	C8—N2—C11—C12	−85.8 (3)
C5—C6—C7—N1	174.51 (19)	C9—N2—C11—C12	95.8 (3)
C7—N1—C8—N2	−178.42 (19)	N2—C11—C12—C13	175.6 (3)
C7—N1—C8—S1	1.5 (3)	C11—C12—C13—C14	−169.4 (4)
C9—N2—C8—N1	179.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.93	2.39	3.309 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.39	3.309 (3)	172

Symmetry code: (i) .