(Z)-N-(3-Nicotinoyl-1,3-thia­zolidin-2-yl­idene)cyanamide

Xie, Y.-M.; Li, Y.-M.

doi:10.1107/S1600536810014406

organic compounds

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Volume 66| Part 5| May 2010| Page o1158

https://doi.org/10.1107/S1600536810014406

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(Z)-N-(3-Nicotinoyl-1,3-thiazolidin-2-ylidene)cyanamide

Yun-Man Xie ^a ^* and Yu-Min Li ^a

^aHenan Chemical Industry Research Institute Co Ltd, Zhengzhou 450052, People's Republic of China
^*Correspondence e-mail: yunman_xie@yahoo.cn

(Received 18 April 2010; accepted 19 April 2010; online 24 April 2010)

In the title compound, C₁₀H₈N₄OS, the dihedral angle between the pyridine and thiazolidine rings is 52.5 (5)°. Intermolecular C—H⋯N interactions help to stabilize the crystal structure.

Related literature

For related structures, see: Wang et al. (2008 ); Liu & Li (2009 ). For the biological activity of thiazolidine-containing compounds, see: Iwata et al. (1988 ); Ogawa (2000 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₀H₈N₄OS
M_r = 232.26
Monoclinic, P 2₁ /c
a = 5.9180 (12) Å
b = 15.182 (3) Å
c = 11.448 (2) Å
β = 94.62 (3)°
V = 1025.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 173 K
0.17 × 0.07 × 0.05 mm

Data collection

Rigaku Mercury CCD/AFC diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ) T_min = 0.951, T_max = 0.985
7491 measured reflections
1799 independent reflections
1699 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.095
S = 1.15
1799 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯N4ⁱ	0.93	2.52	3.383 (3)	154
C8—H8B⋯N1ⁱⁱ	0.97	2.55	3.481 (3)	162
Symmetry codes: (i) $[x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z.

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: https://doi.org/10.1107/S1600536810014406/hg2674sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810014406/hg2674Isup2.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; Ogawa, 2000). In order to search for new thiazolidine compounds with higher bioactivity, we synthesized the title compound and describe its structure here.

In title compound, all bond lengths in the molecular are normal (Allen et al., 1987) and in a good agreement with those reported previously (Wang et al., 2008; Liu & Li, 2009). The dihedral angle between pyridine (C1—C5/N1) and thiazolidine (C7—C9/N2/S1) rings is 52.5 (5)°. The intermolecular C—H···N hydrogen bonds stabilize the structure.

Related literature top

For related structures, see: Wang et al. (2008); Liu & Li (2009). For the biological activity of thiazolidine-containing compounds, see: Iwata et al. (1988); Ogawa (2000). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of N-cyanoiminothiazolidine 10 mmol (1.27 g), nicotinoyl chloride (1.42 g, 10 mmol) and (1.01 g, 10 mmol ) triethylamine is refluxed in absolute acetone (25 ml) for 4 h. On cooling, the product crystallizes and is filtered, and recrystallized from absolute EtOH, yield 2.13 g (92%). Single crystals suitable for X-ray measurements were obtained by recrystallization from dichloromethane at room temperature.

Structure description top

For related structures, see: Wang et al. (2008); Liu & Li (2009). For the biological activity of thiazolidine-containing compounds, see: Iwata et al. (1988); Ogawa (2000). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), with atom labels and 40% probability displacement ellipsoids for non-H atoms.

(Z)-N-(3-Nicotinoyl-1,3-thiazolidin-2-ylidene)cyanamide top

Crystal data top

C₁₀H₈N₄OS	F(000) = 480
M_r = 232.26	D_x = 1.505 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3351 reflections
a = 5.9180 (12) Å	θ = 1.3–27.5°
b = 15.182 (3) Å	µ = 0.30 mm⁻¹
c = 11.448 (2) Å	T = 173 K
β = 94.62 (3)°	Needle, colorless
V = 1025.2 (4) Å³	0.17 × 0.07 × 0.05 mm
Z = 4

Data collection top

Rigaku Mercury CCD/AFC diffractometer	1799 independent reflections
Radiation source: Sealed Tube	1699 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.054
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	h = −6→7
T_min = 0.951, T_max = 0.985	k = −18→18
7491 measured reflections	l = −13→13

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0269P)² + 0.7053P] where P = (F_o² + 2F_c²)/3
1799 reflections	(Δ/σ)_max = 0.001
145 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₀H₈N₄OS	V = 1025.2 (4) Å³
M_r = 232.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.9180 (12) Å	µ = 0.30 mm⁻¹
b = 15.182 (3) Å	T = 173 K
c = 11.448 (2) Å	0.17 × 0.07 × 0.05 mm
β = 94.62 (3)°

Data collection top

Rigaku Mercury CCD/AFC diffractometer	1799 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	1699 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.985	R_int = 0.054
7491 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.15	Δρ_max = 0.28 e Å⁻³
1799 reflections	Δρ_min = −0.19 e Å⁻³
145 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1	0.07382 (9)	0.71271 (4)	0.18314 (5)	0.02782 (18)
O1	0.6823 (2)	0.58746 (10)	−0.01165 (14)	0.0305 (4)
N1	0.0795 (3)	0.54439 (13)	−0.29129 (17)	0.0316 (5)
N2	0.3613 (3)	0.63953 (12)	0.05512 (15)	0.0230 (4)
N3	0.0875 (3)	0.72532 (12)	−0.05117 (15)	0.0253 (4)
N4	−0.2685 (4)	0.81222 (15)	−0.06511 (18)	0.0426 (6)
C1	0.5188 (4)	0.60983 (14)	−0.2489 (2)	0.0264 (5)
H1A	0.6663	0.6306	−0.2347	0.032*
C2	0.4329 (4)	0.58936 (16)	−0.3616 (2)	0.0318 (5)
H2A	0.5202	0.5972	−0.4248	0.038*
C3	0.2154 (4)	0.55716 (16)	−0.3780 (2)	0.0338 (6)
H3B	0.1591	0.5434	−0.4540	0.041*
C4	0.1635 (4)	0.56544 (14)	−0.1829 (2)	0.0262 (5)
H4A	0.0720	0.5573	−0.1214	0.031*
C5	0.3806 (3)	0.59877 (13)	−0.15738 (19)	0.0217 (5)
C6	0.4871 (4)	0.60973 (13)	−0.03604 (19)	0.0228 (5)
C7	0.4663 (4)	0.63253 (15)	0.17646 (18)	0.0254 (5)
H7A	0.5699	0.6811	0.1940	0.030*
H7B	0.5496	0.5777	0.1871	0.030*
C8	0.2732 (4)	0.63538 (15)	0.25500 (19)	0.0268 (5)
H8A	0.3252	0.6557	0.3329	0.032*
H8B	0.2048	0.5777	0.2611	0.032*
C9	0.1716 (3)	0.69261 (14)	0.04735 (19)	0.0222 (5)
C10	−0.1045 (4)	0.77156 (15)	−0.05189 (18)	0.0280 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0233 (3)	0.0389 (4)	0.0215 (3)	0.0052 (2)	0.0034 (2)	−0.0013 (2)
O1	0.0204 (9)	0.0388 (9)	0.0324 (9)	0.0057 (7)	0.0024 (6)	0.0012 (7)
N1	0.0276 (11)	0.0311 (11)	0.0363 (12)	−0.0026 (8)	0.0029 (9)	−0.0036 (9)
N2	0.0185 (9)	0.0278 (10)	0.0228 (10)	0.0038 (7)	0.0023 (7)	0.0007 (8)
N3	0.0237 (10)	0.0293 (10)	0.0232 (10)	0.0055 (8)	0.0044 (7)	0.0029 (8)
N4	0.0399 (13)	0.0566 (14)	0.0306 (12)	0.0207 (12)	−0.0015 (9)	−0.0012 (10)
C1	0.0205 (11)	0.0250 (11)	0.0342 (13)	−0.0001 (9)	0.0058 (9)	−0.0007 (10)
C2	0.0334 (14)	0.0362 (13)	0.0272 (13)	0.0006 (11)	0.0104 (10)	−0.0007 (10)
C3	0.0368 (14)	0.0371 (14)	0.0272 (13)	−0.0029 (11)	0.0006 (10)	−0.0058 (10)
C4	0.0252 (12)	0.0246 (11)	0.0300 (12)	0.0030 (9)	0.0088 (9)	0.0000 (9)
C5	0.0192 (11)	0.0197 (10)	0.0267 (11)	0.0029 (8)	0.0037 (8)	0.0000 (9)
C6	0.0202 (12)	0.0202 (11)	0.0286 (12)	−0.0009 (9)	0.0057 (9)	0.0007 (9)
C7	0.0232 (12)	0.0272 (11)	0.0252 (12)	0.0028 (9)	−0.0014 (9)	−0.0013 (9)
C8	0.0259 (12)	0.0303 (12)	0.0237 (12)	−0.0016 (10)	−0.0014 (9)	0.0030 (9)
C9	0.0176 (11)	0.0222 (10)	0.0270 (12)	−0.0015 (9)	0.0034 (9)	−0.0004 (9)
C10	0.0311 (13)	0.0344 (12)	0.0187 (11)	0.0057 (11)	0.0037 (9)	−0.0003 (9)

Geometric parameters (Å, º) top

S1—C9	1.729 (2)	C1—H1A	0.9300
S1—C8	1.814 (2)	C2—C3	1.376 (3)
O1—C6	1.214 (3)	C2—H2A	0.9300
N1—C4	1.338 (3)	C3—H3B	0.9300
N1—C3	1.342 (3)	C4—C5	1.390 (3)
N2—C9	1.379 (3)	C4—H4A	0.9300
N2—C6	1.405 (3)	C5—C6	1.488 (3)
N2—C7	1.479 (3)	C7—C8	1.510 (3)
N3—C9	1.295 (3)	C7—H7A	0.9700
N3—C10	1.335 (3)	C7—H7B	0.9700
N4—C10	1.150 (3)	C8—H8A	0.9700
C1—C2	1.383 (3)	C8—H8B	0.9700
C1—C5	1.391 (3)

C9—S1—C8	92.34 (10)	C1—C5—C6	117.34 (19)
C4—N1—C3	116.86 (19)	O1—C6—N2	118.05 (19)
C9—N2—C6	128.16 (18)	O1—C6—C5	120.49 (19)
C9—N2—C7	112.40 (17)	N2—C6—C5	121.28 (18)
C6—N2—C7	117.80 (17)	N2—C7—C8	106.01 (17)
C9—N3—C10	118.32 (18)	N2—C7—H7A	110.5
C2—C1—C5	118.8 (2)	C8—C7—H7A	110.5
C2—C1—H1A	120.6	N2—C7—H7B	110.5
C5—C1—H1A	120.6	C8—C7—H7B	110.5
C3—C2—C1	118.5 (2)	H7A—C7—H7B	108.7
C3—C2—H2A	120.8	C7—C8—S1	104.14 (14)
C1—C2—H2A	120.8	C7—C8—H8A	110.9
N1—C3—C2	124.1 (2)	S1—C8—H8A	110.9
N1—C3—H3B	118.0	C7—C8—H8B	110.9
C2—C3—H3B	118.0	S1—C8—H8B	110.9
N1—C4—C5	123.4 (2)	H8A—C8—H8B	108.9
N1—C4—H4A	118.3	N3—C9—N2	122.30 (19)
C5—C4—H4A	118.3	N3—C9—S1	125.63 (17)
C4—C5—C1	118.4 (2)	N2—C9—S1	112.01 (15)
C4—C5—C6	123.50 (19)	N4—C10—N3	172.7 (2)

C5—C1—C2—C3	−1.3 (3)	C1—C5—C6—N2	150.65 (19)
C4—N1—C3—C2	0.6 (4)	C9—N2—C7—C8	34.3 (2)
C1—C2—C3—N1	0.2 (4)	C6—N2—C7—C8	−159.14 (18)
C3—N1—C4—C5	−0.3 (3)	N2—C7—C8—S1	−36.57 (19)
N1—C4—C5—C1	−0.8 (3)	C9—S1—C8—C7	25.54 (16)
N1—C4—C5—C6	−170.6 (2)	C10—N3—C9—N2	175.9 (2)
C2—C1—C5—C4	1.6 (3)	C10—N3—C9—S1	−7.2 (3)
C2—C1—C5—C6	172.0 (2)	C6—N2—C9—N3	−2.5 (3)
C9—N2—C6—O1	157.6 (2)	C7—N2—C9—N3	162.4 (2)
C7—N2—C6—O1	−6.6 (3)	C6—N2—C9—S1	−179.73 (17)
C9—N2—C6—C5	−27.3 (3)	C7—N2—C9—S1	−14.8 (2)
C7—N2—C6—C5	168.55 (18)	C8—S1—C9—N3	175.7 (2)
C4—C5—C6—O1	135.5 (2)	C8—S1—C9—N2	−7.10 (17)
C1—C5—C6—O1	−34.3 (3)	C9—N3—C10—N4	−178 (2)
C4—C5—C6—N2	−39.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N4ⁱ	0.93	2.52	3.383 (3)	154
C8—H8B···N1ⁱⁱ	0.97	2.55	3.481 (3)	162

Symmetry codes: (i) x+1, −y+3/2, z−1/2; (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₄OS
M_r	232.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	5.9180 (12), 15.182 (3), 11.448 (2)
β (°)	94.62 (3)
V (Å³)	1025.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.17 × 0.07 × 0.05

Data collection
Diffractometer	Rigaku Mercury CCD/AFC
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.951, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	7491, 1799, 1699
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.095, 1.15
No. of reflections	1799
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.19

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N4ⁱ	0.93	2.52	3.383 (3)	154.2
C8—H8B···N1ⁱⁱ	0.97	2.55	3.481 (3)	162.1

Symmetry codes: (i) x+1, −y+3/2, z−1/2; (ii) −x, −y+1, −z.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Iwata, C., Watanabe, M., Okamoto, S., Fujimoto, M., Sakae, M., Katsurada, M. & Imanishi, T. (1988). Synthesis, pp. 261–262. Google Scholar
Liu, X.-L. & Li, Y.-M. (2009). Acta Cryst. E65, o1645. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ogawa, T. (2000). Jpn Patent JP 2000226378. Google Scholar
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, J.-G., Huang, L.-H. & Jian, F.-F. (2008). Acta Cryst. E64, o2321. Web of Science CSD CrossRef IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1158

https://doi.org/10.1107/S1600536810014406

Open

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