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

In the title compound, C(18)H(24)N(2)O(2)S, the thia-zolidinone ring is almost coplanar [maximum atomic deviation = 0.017 (3) Å], and is coplanar with the phenyl ring [dihedral angle = 0.62 (13)°]. The octyl group displays an extended conformation. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into supra-molecular chains along [210].

Related literature

For pharmaceutical applications of thia­zolidinones, see: Dwivedi et al. (1972 ▶); Chandrakant et al. (2004 ▶). For the synthesis, see: Peng et al. (2004 ▶).

Experimental

Crystal data

C18H24N2O2S

M = 332.45

Triclinic,

a = 5.3342 (3) Å

b = 8.6196 (5) Å

c = 20.0775 (12) Å

α = 97.008 (5)°

β = 92.870 (4)°

γ = 99.477 (4)°

V = 901.41 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 293 K

0.26 × 0.18 × 0.16 mm

Data collection

Oxford Diffraction Nova A diffractometer

8685 measured reflections

3205 independent reflections

2371 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.145

S = 1.03

3205 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047884/xu5080sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047884/xu5080Isup2.hkl

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

C18H24N2O2S	Z = 2
Mr = 332.45	F(000) = 356
Triclinic, P1	Dx = 1.225 Mg m−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3342 (3) Å	Cell parameters from 2856 reflections
b = 8.6196 (5) Å	θ = 4.5–67.0°
c = 20.0775 (12) Å	µ = 0.19 mm−1
α = 97.008 (5)°	T = 293 K
β = 92.870 (4)°	Prism, yellow
γ = 99.477 (4)°	0.26 × 0.18 × 0.16 mm
V = 901.41 (9) Å3

Oxford Diffraction Nova A diffractometer	2371 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
graphite	θmax = 25.1°, θmin = 2.1°
ω scans	h = −6→5
8685 measured reflections	k = −9→10
3205 independent reflections	l = −23→23

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0633P)2 + 0.4272P] where P = (Fo2 + 2Fc2)/3
3205 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
N2	0.2339 (4)	0.3596 (2)	0.30556 (10)	0.0496 (5)
N1	−0.1304 (4)	0.2176 (2)	0.34097 (10)	0.0492 (5)
C9	0.4393 (5)	0.4805 (3)	0.32305 (14)	0.0533 (6)
C8	0.0680 (5)	0.3283 (3)	0.35492 (12)	0.0464 (6)
C10	0.4427 (5)	0.5499 (3)	0.39502 (14)	0.0585 (7)
H10A	0.4422	0.6630	0.3982	0.070*
H10B	0.5952	0.5337	0.4197	0.070*
O1	−0.2580 (4)	0.2654 (2)	0.44909 (9)	0.0680 (6)
O2	0.5957 (4)	0.5200 (2)	0.28388 (11)	0.0733 (6)
S1	0.16338 (13)	0.45285 (8)	0.42998 (3)	0.0534 (2)
C7	−0.2882 (5)	0.1901 (3)	0.39283 (13)	0.0508 (6)
C1	−0.5089 (5)	0.0581 (3)	0.37455 (13)	0.0495 (6)
C11	0.1963 (5)	0.2715 (3)	0.23775 (13)	0.0569 (7)
H11A	0.1125	0.1638	0.2402	0.068*
H11B	0.3613	0.2663	0.2202	0.068*
C2	−0.5494 (5)	−0.0279 (3)	0.31152 (14)	0.0598 (7)
H2	−0.4341	−0.0064	0.2792	0.072*
C6	−0.6820 (5)	0.0229 (3)	0.42264 (15)	0.0606 (7)
H6	−0.6555	0.0795	0.4656	0.073*
C5	−0.8909 (6)	−0.0944 (4)	0.40707 (18)	0.0712 (8)
H5	−1.0049	−0.1172	0.4395	0.085*
C4	−0.9324 (6)	−0.1783 (4)	0.34373 (19)	0.0735 (9)
H4	−1.0759	−0.2565	0.3331	0.088*
C13	−0.0006 (7)	0.2535 (5)	0.12043 (15)	0.0816 (10)
H13A	0.1634	0.2576	0.1013	0.098*
H13B	−0.0658	0.1432	0.1241	0.098*
C12	0.0397 (6)	0.3448 (4)	0.18997 (14)	0.0730 (9)
H12A	0.1241	0.4523	0.1872	0.088*
H12B	−0.1249	0.3508	0.2077	0.088*
C3	−0.7605 (6)	−0.1462 (4)	0.29574 (17)	0.0721 (9)
H3	−0.7867	−0.2041	0.2530	0.086*
C15	−0.2276 (8)	0.2222 (6)	0.00389 (18)	0.1053 (13)
H15A	−0.2838	0.1109	0.0076	0.126*
H15B	−0.0679	0.2307	−0.0176	0.126*
C14	−0.1781 (8)	0.3108 (5)	0.07302 (17)	0.0976 (12)
H14A	−0.3401	0.3090	0.0930	0.117*
H14B	−0.1106	0.4207	0.0691	0.117*
C17	−0.4809 (10)	0.1911 (7)	−0.1089 (2)	0.1358 (19)
H17A	−0.5318	0.0792	−0.1055	0.163*
H17B	−0.3262	0.2022	−0.1326	0.163*
C16	−0.4209 (9)	0.2749 (6)	−0.04136 (19)	0.1114 (14)
H16A	−0.5784	0.2690	−0.0189	0.134*
H16B	−0.3621	0.3859	−0.0452	0.134*
C18	−0.6818 (9)	0.2415 (7)	−0.1504 (2)	0.1289 (18)
H18A	−0.7081	0.1765	−0.1933	0.193*
H18B	−0.6304	0.3505	−0.1567	0.193*
H18C	−0.8375	0.2302	−0.1280	0.193*

	U11	U22	U33	U12	U13	U23
N2	0.0480 (11)	0.0528 (12)	0.0450 (11)	0.0005 (10)	0.0052 (9)	0.0055 (9)
N1	0.0485 (11)	0.0499 (12)	0.0463 (12)	0.0009 (10)	0.0016 (9)	0.0058 (9)
C9	0.0484 (14)	0.0498 (15)	0.0606 (16)	0.0042 (12)	0.0051 (12)	0.0080 (12)
C8	0.0474 (13)	0.0485 (14)	0.0435 (13)	0.0085 (11)	0.0025 (10)	0.0074 (11)
C10	0.0509 (15)	0.0552 (16)	0.0643 (17)	−0.0023 (12)	−0.0024 (13)	0.0066 (13)
O1	0.0687 (12)	0.0731 (13)	0.0520 (11)	−0.0099 (10)	0.0110 (9)	−0.0052 (10)
O2	0.0613 (12)	0.0734 (14)	0.0804 (14)	−0.0074 (10)	0.0208 (11)	0.0104 (11)
S1	0.0525 (4)	0.0583 (4)	0.0445 (4)	0.0010 (3)	0.0008 (3)	−0.0002 (3)
C7	0.0477 (14)	0.0528 (15)	0.0519 (15)	0.0065 (12)	0.0025 (11)	0.0100 (12)
C1	0.0447 (13)	0.0500 (14)	0.0537 (15)	0.0063 (11)	0.0025 (11)	0.0099 (12)
C11	0.0572 (15)	0.0606 (16)	0.0497 (15)	0.0037 (13)	0.0105 (12)	0.0012 (13)
C2	0.0558 (16)	0.0597 (17)	0.0600 (17)	−0.0015 (13)	0.0014 (13)	0.0091 (14)
C6	0.0517 (15)	0.0645 (18)	0.0671 (18)	0.0083 (13)	0.0082 (13)	0.0153 (14)
C5	0.0541 (17)	0.073 (2)	0.089 (2)	0.0048 (15)	0.0147 (16)	0.0263 (18)
C4	0.0518 (16)	0.0626 (19)	0.102 (3)	−0.0080 (14)	−0.0050 (17)	0.0241 (18)
C13	0.088 (2)	0.097 (3)	0.0558 (18)	0.011 (2)	0.0007 (16)	0.0037 (17)
C12	0.077 (2)	0.086 (2)	0.0543 (17)	0.0132 (17)	0.0032 (15)	0.0036 (16)
C3	0.0703 (19)	0.0631 (19)	0.073 (2)	−0.0051 (15)	−0.0111 (16)	0.0013 (15)
C15	0.116 (3)	0.130 (4)	0.063 (2)	0.014 (3)	−0.010 (2)	0.004 (2)
C14	0.105 (3)	0.122 (3)	0.063 (2)	0.018 (2)	−0.0113 (19)	0.009 (2)
C17	0.153 (4)	0.185 (5)	0.068 (3)	0.049 (4)	−0.022 (3)	−0.004 (3)
C16	0.120 (3)	0.137 (4)	0.073 (2)	0.021 (3)	−0.012 (2)	0.006 (2)
C18	0.129 (4)	0.182 (5)	0.076 (3)	0.042 (4)	−0.017 (3)	0.003 (3)

N2—C9	1.380 (3)	C4—C3	1.384 (5)
N2—C8	1.383 (3)	C4—H4	0.9300
N2—C11	1.463 (3)	C13—C14	1.492 (5)
N1—C8	1.297 (3)	C13—C12	1.504 (4)
N1—C7	1.390 (3)	C13—H13A	0.9700
C9—O2	1.212 (3)	C13—H13B	0.9700
C9—C10	1.493 (4)	C12—H12A	0.9700
C8—S1	1.741 (2)	C12—H12B	0.9700
C10—S1	1.802 (3)	C3—H3	0.9300
C10—H10A	0.9700	C15—C14	1.489 (5)
C10—H10B	0.9700	C15—C16	1.502 (5)
O1—C7	1.221 (3)	C15—H15A	0.9700
C7—C1	1.493 (4)	C15—H15B	0.9700
C1—C2	1.374 (4)	C14—H14A	0.9700
C1—C6	1.395 (4)	C14—H14B	0.9700
C11—C12	1.503 (4)	C17—C16	1.451 (5)
C11—H11A	0.9700	C17—C18	1.477 (6)
C11—H11B	0.9700	C17—H17A	0.9700
C2—C3	1.384 (4)	C17—H17B	0.9700
C2—H2	0.9300	C16—H16A	0.9700
C6—C5	1.371 (4)	C16—H16B	0.9700
C6—H6	0.9300	C18—H18A	0.9600
C5—C4	1.373 (5)	C18—H18B	0.9600
C5—H5	0.9300	C18—H18C	0.9600
C9—N2—C8	116.6 (2)	C12—C13—H13A	108.5
C9—N2—C11	120.8 (2)	C14—C13—H13B	108.5
C8—N2—C11	122.6 (2)	C12—C13—H13B	108.5
C8—N1—C7	116.6 (2)	H13A—C13—H13B	107.5
O2—C9—N2	122.6 (3)	C11—C12—C13	113.0 (3)
O2—C9—C10	126.0 (2)	C11—C12—H12A	109.0
N2—C9—C10	111.4 (2)	C13—C12—H12A	109.0
N1—C8—N2	119.3 (2)	C11—C12—H12B	109.0
N1—C8—S1	128.94 (19)	C13—C12—H12B	109.0
N2—C8—S1	111.79 (18)	H12A—C12—H12B	107.8
C9—C10—S1	108.19 (18)	C2—C3—C4	119.8 (3)
C9—C10—H10A	110.1	C2—C3—H3	120.1
S1—C10—H10A	110.1	C4—C3—H3	120.1
C9—C10—H10B	110.1	C14—C15—C16	116.1 (4)
S1—C10—H10B	110.1	C14—C15—H15A	108.3
H10A—C10—H10B	108.4	C16—C15—H15A	108.3
C8—S1—C10	91.98 (12)	C14—C15—H15B	108.3
O1—C7—N1	125.0 (2)	C16—C15—H15B	108.3
O1—C7—C1	120.7 (2)	H15A—C15—H15B	107.4
N1—C7—C1	114.3 (2)	C15—C14—C13	117.1 (4)
C2—C1—C6	119.0 (2)	C15—C14—H14A	108.0
C2—C1—C7	122.1 (2)	C13—C14—H14A	108.0
C6—C1—C7	118.9 (2)	C15—C14—H14B	108.0
N2—C11—C12	113.0 (2)	C13—C14—H14B	108.0
N2—C11—H11A	109.0	H14A—C14—H14B	107.3
C12—C11—H11A	109.0	C16—C17—C18	116.8 (4)
N2—C11—H11B	109.0	C16—C17—H17A	108.1
C12—C11—H11B	109.0	C18—C17—H17A	108.1
H11A—C11—H11B	107.8	C16—C17—H17B	108.1
C1—C2—C3	120.5 (3)	C18—C17—H17B	108.1
C1—C2—H2	119.7	H17A—C17—H17B	107.3
C3—C2—H2	119.7	C17—C16—C15	118.6 (4)
C5—C6—C1	120.5 (3)	C17—C16—H16A	107.7
C5—C6—H6	119.7	C15—C16—H16A	107.7
C1—C6—H6	119.7	C17—C16—H16B	107.7
C6—C5—C4	120.2 (3)	C15—C16—H16B	107.7
C6—C5—H5	119.9	H16A—C16—H16B	107.1
C4—C5—H5	119.9	C17—C18—H18A	109.5
C5—C4—C3	119.9 (3)	C17—C18—H18B	109.5
C5—C4—H4	120.0	H18A—C18—H18B	109.5
C3—C4—H4	120.0	C17—C18—H18C	109.5
C14—C13—C12	115.2 (3)	H18A—C18—H18C	109.5
C14—C13—H13A	108.5	H18B—C18—H18C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2i	0.93	2.45	3.365 (4)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2i	0.93	2.45	3.365 (4)	168

Symmetry code: (i) .