N-(3-Octyl-4-oxo-1,3-thia­zolidin-2-yl­idene)benzamide

Zhao, H.-R.; Wang, H.-Y.; Meng, X.-W.

doi:10.1107/S1600536810047884

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3285

https://doi.org/10.1107/S1600536810047884

Open

access

N-(3-Octyl-4-oxo-1,3-thiazolidin-2-ylidene)benzamide

Hua-Rong Zhao,^a ^* Hai-Yan Wang ^a and Xiang-Wu Meng ^a

^aDepartment of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China
^*Correspondence e-mail: zhr0103@zju.edu.cn

(Received 1 November 2010; accepted 17 November 2010; online 24 November 2010)

In the title compound, C₁₈H₂₄N₂O₂S, the thiazolidinone 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 intermolecular C—H⋯O hydrogen bonds link the molecules into supramolecular 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_r = 332.45
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.145
S = 1.03
3205 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) x-2, y-1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810047884/xu5080Isup2.hkl

checkCIF report

Comment top

Thiazolidinones have broad applications as anticonvulsant (Dwivedi et al., 1972) and anti-microbial drugs (Chandrakant et al., 2004). We report here the structure of a new thiazolidinone derivative, I, Fig. 2.

The thiazolidinyl ring and phenyl ring are almost co-planar with the dihedral angle of 0.67 (0.18)°. In the crystal structure, weak intermolecular C—H···O hydrogen bonds, Table 1, link the molecules to form one-dimensional supra-molecular chains, Fig. 1.

Related literature top

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

Experimental top

The title compound was prepared followed to the procedure reported by Peng et al. (2004). NH₄SCN (0.152 g, 2 mmol) and [bmim][PF₄] (2 ml) was mixed in a 50 ml flask equipped with a dropping funnel and then was cooled in an ice-water bath. Next benzoyl chloride(0.284 g, 2 mmol) was added drop by drop and stirred for a further 20 min (disappearance of the raw material was monitored by TLC). n-Octylamine (2 mmol) was then added to the same reaction vessel at room temperature and the mixture was stirred for 20 min more. N-benzoyl-N'-octylthiourea was formed. After that, ethyl chloroacetate (2.4 mmol) and anhydrous sodium acetate (0.196 g, 2.4 mmol) was added to the flask, and the mixture was heated at 80°C for 2 h. The salts were firstly leached with water (10 ml×2), and the crude product was collected by filtration. Recrystallization from ethanol gave pure product as a yellow crystalline solid.

Structure description top

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

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); 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).

Figures top

	Fig. 1. The molecular structure of the title compound with 40% probability displacement ellipsoids.
	Fig. 2. Crystal packing for I viewed down the a axis.

N-(3-Octyl-4-oxo-1,3-thiazolidin-2-ylidene)benzamide top

Crystal data top

C₁₈H₂₄N₂O₂S	Z = 2
M_r = 332.45	F(000) = 356
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0633P)² + 0.4272P] where P = (F_o² + 2F_c²)/3
3205 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₈H₂₄N₂O₂S	γ = 99.477 (4)°
M_r = 332.45	V = 901.41 (9) Å³
Triclinic, P1	Z = 2
a = 5.3342 (3) Å	Mo Kα radiation
b = 8.6196 (5) Å	µ = 0.19 mm⁻¹
c = 20.0775 (12) Å	T = 293 K
α = 97.008 (5)°	0.26 × 0.18 × 0.16 mm
β = 92.870 (4)°

Data collection top

Oxford Diffraction Nova A diffractometer	2371 reflections with I > 2σ(I)
8685 measured reflections	R_int = 0.039
3205 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.03	Δρ_max = 0.18 e Å⁻³
3205 reflections	Δρ_min = −0.17 e Å⁻³
208 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x−2, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₄N₂O₂S
M_r	332.45
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.3342 (3), 8.6196 (5), 20.0775 (12)
α, β, γ (°)	97.008 (5), 92.870 (4), 99.477 (4)
V (Å³)	901.41 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.26 × 0.18 × 0.16

Data collection
Diffractometer	Oxford Diffraction Nova A
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8685, 3205, 2371
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.145, 1.03
No. of reflections	3205
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.17

Computer programs: CrysAlis PRO (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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) x−2, y−1, z.

Acknowledgements

The authors thank the Natural Science Foundation of Zhejiang Province, China, for financial support (grant No. Y4080234).

References

Chandrakant, G. & Gaikwad, N. G. (2004). Bioorg. Med. Chem. 12, 2151–2161. Web of Science PubMed Google Scholar
Dwivedi, C., Gupta, T. K. & Parmar, S. S. (1972). J. Med. Chem. 15, 553–554. CrossRef CAS PubMed Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2008). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Peng, Y.-Q., Song, G.-H. & Huang, F.-F. (2004). J. Chem. Res. 10, 676–678. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar