N-[(Z)-3-(4-Chloro­benzo­yl)-1,3-thia­zolidin-2-yl­idene]cyanamide

Wang, J.-G.; Huang, L.-H.; Jian, F.-F.

doi:10.1107/S1600536808036568

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2321

doi:10.1107/S1600536808036568

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N-[(Z)-3-(4-Chlorobenzoyl)-1,3-thiazolidin-2-ylidene]cyanamide

Jian-Gang Wang,^a Li-Hua Huang ^b and Fang-Fang Jian ^c ^*

^aMicroscale Science Institute, Biology Department, Weifang University, Weifang 261061, People's Republic of China, ^bNew Materials and Functional Coordination Chemistry Laboratory, Qingdao University of Science and Technology, Qingdao 266042 People's Republic of China, and ^cMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 8 October 2008; accepted 7 November 2008; online 13 November 2008)

The title compound, C₁₁H₈ClN₃OS, was prepared by the reaction of N-cyanoiminothiazolidine, 2-aminoethanethiol and triethylamine at 350 K. The dihedral angle between the two rings is 62.5 (8)°.

Related literature

For the biological activities of thiazolidine compounds, see: Iwata et al. (1988 ); Huang & Shi (1990 ). For related structures, see Jian et al. (2006 ); Schroth et al. (1997 ).

Experimental

Crystal data

C₁₁H₈ClN₃OS
M_r = 265.72
Monoclinic, P 2₁ /c
a = 16.442 (3) Å
b = 5.6798 (11) Å
c = 13.313 (3) Å
β = 112.76 (3)°
V = 1146.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 293 (2) K
0.34 × 0.21 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
8343 measured reflections
2016 independent reflections
1915 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.066
S = 1.13
2016 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 2001 ); 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 global, I. DOI: 10.1107/S1600536808036568/pk2128sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808036568/pk2128Isup2.hkl

checkCIF report

Comment top

Thiazolidine is an important group in organic chemistry. Many compounds containing thiazolidine groups possess a broad spectrum of biological activities (Iwata et al., 1988; Huang & Shi, 1990).

In the crystal structure (Fig. 1), the torsion angle formed by atoms N1, C8, C9 and S1 was 34.5 (9)°. The dihedral angle formed by the the ring (N1, C8, C9, C10 and S1) and the phenyl ring (C1-C6) was 62.5 (8)°. The C=N bond length (1.299 (2) Å) is in agreement with that observed before (Jian et al., 2006). The C—S bond length (1.734 (7) and 1.808 (2) Å) are in agreement with those observed before (Schroth et al., 1997). Intermolecular C–H···N interactions help to stabilize the crystal structure.

Related literature top

For the biological activities of thiazolidine compounds, see: Iwata et al. (1988); Huang & Shi (1990). For related structures, see Jian et al. (2006); Schroth et al. (1997).

Experimental top

A mixture of N-cyanoiminothiazolidine 10 mmol (1.27 g), 2-amino-ethanethiol (1.75 g, 10 mmol) and (1.01 g, 10 mmol) triethylamine was refluxed in absolute acetone (25 ml) for 4 h. On cooling, the product crystallized, was filtered, and recrystallized from absolute EtOH (yield 2.42 g (91%)). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); 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 compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 40% probability level.

N-[(Z)-3-(4-Chlorobenzoyl)-1,3-thiazolidin-2-ylidene]cyanamide top

Crystal data top

C₁₁H₈ClN₃OS	F(000) = 544
M_r = 265.72	D_x = 1.539 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1021 reflections
a = 16.442 (3) Å	θ = 2.9–26.4°
b = 5.6798 (11) Å	µ = 0.50 mm⁻¹
c = 13.313 (3) Å	T = 293 K
β = 112.76 (3)°	Block, colorless
V = 1146.5 (5) Å³	0.34 × 0.21 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	1915 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 25.0°, θ_min = 3.1°
ϕ and ω scans	h = −19→19
8343 measured reflections	k = −6→6
2016 independent reflections	l = −15→15

Refinement top

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)] = 0.026	H-atom parameters constrained
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.017P)² + 0.7287P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.001
2016 reflections	Δρ_max = 0.21 e Å⁻³
155 parameters	Δρ_min = −0.22 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: 0.031 (2)

Crystal data top

C₁₁H₈ClN₃OS	V = 1146.5 (5) Å³
M_r = 265.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.442 (3) Å	µ = 0.50 mm⁻¹
b = 5.6798 (11) Å	T = 293 K
c = 13.313 (3) Å	0.34 × 0.21 × 0.15 mm
β = 112.76 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1915 reflections with I > 2σ(I)
8343 measured reflections	R_int = 0.030
2016 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.066	H-atom parameters constrained
S = 1.13	Δρ_max = 0.21 e Å⁻³
2016 reflections	Δρ_min = −0.22 e Å⁻³
155 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
S1	0.07965 (3)	0.52934 (7)	0.33331 (3)	0.02469 (14)
Cl1	0.46689 (3)	0.71315 (8)	0.06338 (3)	0.03512 (15)
O1	0.27367 (8)	1.17756 (19)	0.37317 (10)	0.0302 (3)
N2	0.16368 (9)	0.5912 (2)	0.19639 (11)	0.0244 (3)
C3	0.40564 (10)	0.7898 (3)	0.13961 (12)	0.0229 (3)
N1	0.20390 (8)	0.8283 (2)	0.35254 (10)	0.0216 (3)
C10	0.15500 (10)	0.6503 (3)	0.28595 (12)	0.0201 (3)
C4	0.40148 (10)	0.6326 (3)	0.21690 (12)	0.0232 (3)
H4A	0.4315	0.4901	0.2281	0.028*
N3	0.08333 (10)	0.2509 (3)	0.08619 (14)	0.0426 (4)
C7	0.26182 (10)	0.9843 (3)	0.33103 (12)	0.0220 (3)
C6	0.30963 (9)	0.9060 (3)	0.26219 (12)	0.0197 (3)
C8	0.16984 (11)	0.9017 (3)	0.43566 (13)	0.0263 (4)
H8A	0.1270	1.0272	0.4077	0.032*
H8B	0.2176	0.9574	0.5007	0.032*
C1	0.31667 (10)	1.0641 (3)	0.18625 (13)	0.0227 (3)
H1A	0.2896	1.2106	0.1779	0.027*
C9	0.12728 (11)	0.6865 (3)	0.46101 (13)	0.0268 (4)
H9A	0.0820	0.7312	0.4872	0.032*
H9B	0.1708	0.5901	0.5158	0.032*
C11	0.11795 (11)	0.4075 (3)	0.14112 (14)	0.0275 (4)
C5	0.35225 (10)	0.6895 (3)	0.27740 (12)	0.0222 (3)
H5A	0.3477	0.5833	0.3281	0.027*
C2	0.36370 (10)	1.0057 (3)	0.12284 (13)	0.0244 (3)
H2B	0.3669	1.1093	0.0704	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0224 (2)	0.0236 (2)	0.0314 (2)	−0.00304 (16)	0.01415 (17)	0.00002 (16)
Cl1	0.0368 (3)	0.0412 (3)	0.0340 (2)	0.00200 (19)	0.02096 (19)	−0.00607 (19)
O1	0.0369 (7)	0.0210 (6)	0.0374 (7)	−0.0065 (5)	0.0194 (5)	−0.0072 (5)
N2	0.0252 (7)	0.0244 (7)	0.0252 (7)	−0.0060 (6)	0.0115 (6)	−0.0039 (6)
C3	0.0187 (7)	0.0266 (8)	0.0226 (8)	−0.0038 (6)	0.0071 (6)	−0.0060 (6)
N1	0.0246 (7)	0.0207 (7)	0.0217 (6)	−0.0036 (5)	0.0114 (5)	−0.0012 (5)
C10	0.0185 (7)	0.0167 (7)	0.0243 (8)	0.0018 (6)	0.0075 (6)	0.0039 (6)
C4	0.0194 (8)	0.0190 (7)	0.0273 (8)	0.0006 (6)	0.0047 (6)	−0.0016 (6)
N3	0.0337 (8)	0.0427 (10)	0.0586 (11)	−0.0120 (8)	0.0257 (8)	−0.0256 (9)
C7	0.0218 (8)	0.0201 (8)	0.0229 (8)	−0.0012 (6)	0.0072 (6)	0.0024 (6)
C6	0.0171 (7)	0.0187 (7)	0.0219 (7)	−0.0047 (6)	0.0062 (6)	−0.0019 (6)
C8	0.0293 (8)	0.0284 (8)	0.0244 (8)	−0.0013 (7)	0.0140 (7)	−0.0026 (7)
C1	0.0209 (8)	0.0171 (7)	0.0289 (8)	−0.0013 (6)	0.0082 (6)	0.0017 (6)
C9	0.0248 (8)	0.0326 (9)	0.0236 (8)	−0.0002 (7)	0.0101 (7)	0.0028 (7)
C11	0.0230 (8)	0.0303 (9)	0.0348 (9)	−0.0025 (7)	0.0172 (7)	−0.0056 (8)
C5	0.0226 (8)	0.0192 (8)	0.0227 (8)	−0.0029 (6)	0.0064 (6)	0.0022 (6)
C2	0.0242 (8)	0.0248 (8)	0.0245 (8)	−0.0030 (7)	0.0099 (6)	0.0040 (7)

Geometric parameters (Å, º) top

S1—C10	1.7347 (15)	N3—C11	1.152 (2)
S1—C9	1.8082 (17)	C7—C6	1.488 (2)
Cl1—C3	1.7390 (16)	C6—C1	1.390 (2)
O1—C7	1.2136 (19)	C6—C5	1.391 (2)
N2—C10	1.299 (2)	C8—C9	1.510 (2)
N2—C11	1.329 (2)	C8—H8A	0.9700
C3—C2	1.382 (2)	C8—H8B	0.9700
C3—C4	1.384 (2)	C1—C2	1.388 (2)
N1—C10	1.379 (2)	C1—H1A	0.9300
N1—C7	1.409 (2)	C9—H9A	0.9700
N1—C8	1.4804 (19)	C9—H9B	0.9700
C4—C5	1.383 (2)	C5—H5A	0.9300
C4—H4A	0.9300	C2—H2B	0.9300

C10—S1—C9	92.05 (8)	N1—C8—H8A	110.5
C10—N2—C11	118.14 (14)	C9—C8—H8A	110.5
C2—C3—C4	121.83 (14)	N1—C8—H8B	110.5
C2—C3—Cl1	119.55 (12)	C9—C8—H8B	110.5
C4—C3—Cl1	118.61 (12)	H8A—C8—H8B	108.7
C10—N1—C7	127.01 (13)	C2—C1—C6	120.72 (14)
C10—N1—C8	113.06 (12)	C2—C1—H1A	119.6
C7—N1—C8	117.11 (13)	C6—C1—H1A	119.6
N2—C10—N1	122.40 (14)	C8—C9—S1	105.01 (11)
N2—C10—S1	125.37 (12)	C8—C9—H9A	110.7
N1—C10—S1	112.17 (11)	S1—C9—H9A	110.7
C5—C4—C3	119.40 (14)	C8—C9—H9B	110.7
C5—C4—H4A	120.3	S1—C9—H9B	110.7
C3—C4—H4A	120.3	H9A—C9—H9B	108.8
O1—C7—N1	118.36 (14)	N3—C11—N2	172.67 (18)
O1—C7—C6	121.78 (14)	C4—C5—C6	119.80 (14)
N1—C7—C6	119.80 (13)	C4—C5—H5A	120.1
C1—C6—C5	119.87 (14)	C6—C5—H5A	120.1
C1—C6—C7	117.87 (14)	C3—C2—C1	118.32 (14)
C5—C6—C7	122.08 (14)	C3—C2—H2B	120.8
N1—C8—C9	106.32 (13)	C1—C2—H2B	120.8

C11—N2—C10—N1	175.68 (14)	N1—C7—C6—C1	138.53 (15)
C11—N2—C10—S1	−7.2 (2)	O1—C7—C6—C5	130.83 (17)
C7—N1—C10—N2	6.7 (2)	N1—C7—C6—C5	−46.3 (2)
C8—N1—C10—N2	167.01 (14)	C10—N1—C8—C9	29.96 (17)
C7—N1—C10—S1	−170.72 (12)	C7—N1—C8—C9	−167.65 (13)
C8—N1—C10—S1	−10.44 (16)	C5—C6—C1—C2	1.9 (2)
C9—S1—C10—N2	172.92 (14)	C7—C6—C1—C2	177.18 (14)
C9—S1—C10—N1	−9.73 (12)	N1—C8—C9—S1	−34.60 (15)
C2—C3—C4—C5	1.7 (2)	C10—S1—C9—C8	25.81 (12)
Cl1—C3—C4—C5	−179.26 (11)	C3—C4—C5—C6	−1.8 (2)
C10—N1—C7—O1	152.51 (15)	C1—C6—C5—C4	0.0 (2)
C8—N1—C7—O1	−7.1 (2)	C7—C6—C5—C4	−175.00 (14)
C10—N1—C7—C6	−30.2 (2)	C4—C3—C2—C1	0.2 (2)
C8—N1—C7—C6	170.18 (13)	Cl1—C3—C2—C1	−178.80 (12)
O1—C7—C6—C1	−44.3 (2)	C6—C1—C2—C3	−2.1 (2)

Experimental details

Crystal data
Chemical formula	C₁₁H₈ClN₃OS
M_r	265.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	16.442 (3), 5.6798 (11), 13.313 (3)
β (°)	112.76 (3)
V (Å³)	1146.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.50
Crystal size (mm)	0.34 × 0.21 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8343, 2016, 1915
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.066, 1.13
No. of reflections	2016
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

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

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin. Google Scholar
Huang, Z. T. & Shi, X. (1990). Synthesis, 2, 162–167. CrossRef Google Scholar
Iwata, C., Watanabe, M., Okamoto, S., Fujimoto, M., Sakae, M., Katstrada, M. & Imanishi, T. (1988). Synthesis, 3, 261–262. Google Scholar
Jian, F.-F., Zhuang, R.-R., Wang, K.-F., Zhao, P.-S. & Xiao, H.-L. (2006). Acta Cryst. E62, o3198–o3199. Web of Science CSD CrossRef IUCr Journals Google Scholar
Schroth, W., Hintzsche, E., Jordan, H., Jende, T., Spitzner, R. & Thondorf, I. (1997). Tetrahedron, 53, 7509–7528. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar