(Z)-N-{3-[(6-Chloro­pyridin-3-yl)meth­yl]-1,3-thia­zolidin-2-yl­idene}cyanamide

Gao, J.-S.; Qiao, J.; Yu, Y.-H.; Hou, G.-F.

doi:10.1107/S1600536811013316

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1140

doi:10.1107/S1600536811013316

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(Z)-N-{3-[(6-Chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene}cyanamide

Jin-Sheng Gao,^a,^b ^* Jun Qiao,^a Ying-Hui Yu ^a and Guang-Feng Hou ^b

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and ^bEngineering Research Center of Pesticide of Heilongjiang Province, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: hgf1000@163.com

(Received 2 April 2011; accepted 8 April 2011; online 16 April 2011)

The asymmetric unit of the title compound, C₁₀H₉ClN₄S, common name thiacloprid, comprises two molecules. In both molecules, the thiazolidine rings are almost planar (with r.m.s. deviations of 0.016 and 0.065 Å) and form dihedral angles of 73.36 (6) and 70.25 (8)° with the 2-chloropyridine rings. In the crystal, intermolecular C—H⋯N hydrogen bonds links the molecules into chains propagating in [ $[\overline1]$ 01].

Related literature

For background to the title compound, a member of the neonicotinoide class of insecticides, see Maienfisch et al. (2003 ). For the synthesis, see Ishimitsu et al., (1991 )

Experimental

Crystal data

C₁₀H₉ClN₄S
M_r = 252.73
Monoclinic, P 2₁ /c
a = 7.1294 (14) Å
b = 35.469 (7) Å
c = 9.0211 (18) Å
β = 97.80 (3)°
V = 2260.1 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 293 K
0.31 × 0.29 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.863, T_max = 0.909
21869 measured reflections
5151 independent reflections
3505 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.137
S = 1.08
5151 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N5ⁱ	0.93	2.55	3.459 (4)	167
C13—H13⋯N1ⁱⁱ	0.93	2.49	3.408 (4)	169
Symmetry codes: (i) x-1, y, z; (ii) x, y, z+1.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013316/kp2319sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013316/kp2319Isup2.hkl

checkCIF report

Comment top

Thiacloprid is the common name of the title compound, which is neonicotinoide class of insecticide. High efficacy and flexible application methods make it well suited for modern integrated pest management programs in many cropping systems (Ishimitsu et al., 1991; Maienfisch et al., 2003). We report here the synthesis and crystal structure of thiacloprid.

The asymmetric unit comprises two molecules; the thiazolidine rings are almost planar, and form the dihedral angles with 2-chloropyridine rings of 73.36 (6) and 70.25 (8)°, respectively (Fig. 1).

In the crystal, the intermolecular C—H···N hydrogen bonds link the molecules to form a chain (Fig. 2, Table 1).

Related literature top

For background of the title compound, a member of the neonicotinoide class of insecticides, see Maienfisch et al. (2003). For the synthesis, see Ishimitsu et al., (1991)

Experimental top

The title compound was synthesised according the reference (Ishimitsu et al., 1991). A mixture of 2-cyanoiminothiazolidine (12.7 g, 0.1 mol), 2-chloro-5-pyridylmethyl-chloride (17.4 g, 0.1 mol), and K₂CO₃ (41.4 g, 0.3 mol) in 150 mL of DMF was heated to 323 K and kept stirring for 7 h. After filtered under reduced pressure, the DMF solution was distilled off. A total of 20.2 g (80.2%) title compound was obtained after the recrystallisation from ethyl acetate (15 mL). The suitable colourless block crystal was picked out for the single crystal X-ray diffaction measurement.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at the 50% probability level for non-H atoms.
	Fig. 2. A partial packing view, showing the hydrogen bonding chain. Dashed lines indicate the hydrogen bonds, no involving H atoms have been omitted for clarity.

(Z)-N-{3-[(6-Chloropyridin-3-yl)methyl]- 1,3-thiazolidin-2-ylidene}cyanamide top

Crystal data top

C₁₀H₉ClN₄S	F(000) = 1040
M_r = 252.73	D_x = 1.486 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12991 reflections
a = 7.1294 (14) Å	θ = 3.1–27.5°
b = 35.469 (7) Å	µ = 0.50 mm⁻¹
c = 9.0211 (18) Å	T = 293 K
β = 97.80 (3)°	Block, colourless
V = 2260.1 (8) Å³	0.31 × 0.29 × 0.20 mm
Z = 8

Data collection top

Rigaku R-AXIS RAPID diffractometer	5151 independent reflections
Radiation source: fine-focus sealed tube	3505 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→9
T_min = 0.863, T_max = 0.909	k = −45→45
21869 measured reflections	l = −11→11

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0595P)² + 0.4995P] where P = (F_o² + 2F_c²)/3
5151 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₀H₉ClN₄S	V = 2260.1 (8) Å³
M_r = 252.73	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.1294 (14) Å	µ = 0.50 mm⁻¹
b = 35.469 (7) Å	T = 293 K
c = 9.0211 (18) Å	0.31 × 0.29 × 0.20 mm
β = 97.80 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5151 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3505 reflections with I > 2σ(I)
T_min = 0.863, T_max = 0.909	R_int = 0.046
21869 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.08	Δρ_max = 0.21 e Å⁻³
5151 reflections	Δρ_min = −0.29 e Å⁻³
289 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
C1	0.8652 (3)	0.04805 (6)	0.2994 (3)	0.0528 (6)
C2	0.7778 (4)	0.05431 (7)	0.4241 (3)	0.0564 (6)
H2	0.8315	0.0461	0.5183	0.068*
C3	0.6087 (4)	0.07309 (7)	0.4038 (3)	0.0541 (6)
H3	0.5443	0.0777	0.4850	0.065*
C4	0.5334 (3)	0.08520 (5)	0.2624 (3)	0.0417 (5)
C5	0.6313 (4)	0.07628 (6)	0.1459 (3)	0.0525 (6)
H5	0.5795	0.0835	0.0500	0.063*
C6	0.3545 (3)	0.10860 (6)	0.2362 (3)	0.0486 (5)
H6A	0.2856	0.1025	0.1390	0.058*
H6B	0.2744	0.1024	0.3115	0.058*
C7	0.4452 (4)	0.16785 (7)	0.3852 (3)	0.0586 (6)
H7A	0.5677	0.1592	0.4331	0.070*
H7B	0.3516	0.1622	0.4507	0.070*
C8	0.4506 (6)	0.20899 (8)	0.3572 (4)	0.0831 (10)
H8A	0.5573	0.2202	0.4200	0.100*
H8B	0.3354	0.2207	0.3811	0.100*
C9	0.4189 (3)	0.16902 (6)	0.1222 (3)	0.0422 (5)
C10	0.4177 (3)	0.17589 (7)	−0.1287 (3)	0.0545 (6)
C11	1.3337 (3)	0.05498 (7)	0.7709 (3)	0.0558 (6)
C12	1.2138 (4)	0.04665 (8)	0.8736 (3)	0.0618 (6)
H12	1.2387	0.0268	0.9406	0.074*
C13	1.0549 (4)	0.06898 (8)	0.8737 (3)	0.0609 (7)
H13	0.9712	0.0646	0.9423	0.073*
C14	1.0214 (3)	0.09783 (7)	0.7712 (3)	0.0523 (6)
C15	1.1509 (4)	0.10300 (8)	0.6735 (3)	0.0665 (7)
H15	1.1280	0.1222	0.6033	0.080*
C16	0.8483 (3)	0.12283 (9)	0.7672 (4)	0.0678 (8)
H16A	0.7818	0.1234	0.6660	0.081*
H16B	0.7636	0.1121	0.8315	0.081*
C17	0.8939 (5)	0.19245 (10)	0.7102 (4)	0.0840 (10)
H17A	0.7664	0.1963	0.6595	0.101*
H17B	0.9753	0.1866	0.6353	0.101*
C18	0.9605 (6)	0.22673 (9)	0.7904 (4)	0.0853 (10)
H18A	0.8799	0.2478	0.7556	0.102*
H18B	1.0887	0.2325	0.7728	0.102*
C19	0.9155 (3)	0.17075 (7)	0.9595 (3)	0.0464 (5)
C20	0.9267 (3)	0.15741 (8)	1.2059 (3)	0.0593 (6)
Cl1	1.08715 (10)	0.02601 (2)	0.31970 (11)	0.0811 (3)
Cl2	1.53924 (11)	0.02813 (2)	0.76846 (10)	0.0809 (2)
N1	0.7967 (3)	0.05776 (6)	0.1620 (3)	0.0592 (5)
N2	0.3963 (2)	0.14899 (5)	0.2425 (2)	0.0432 (4)
N3	0.4000 (3)	0.15412 (5)	−0.0121 (2)	0.0504 (5)
N4	0.4288 (4)	0.19221 (7)	−0.2375 (3)	0.0777 (7)
N5	1.3080 (3)	0.08234 (7)	0.6720 (3)	0.0658 (6)
N6	0.8957 (3)	0.16118 (6)	0.8155 (2)	0.0540 (5)
N7	0.9051 (3)	0.14604 (6)	1.0652 (2)	0.0551 (5)
N8	0.9439 (4)	0.16423 (9)	1.3319 (3)	0.0864 (8)
S1	0.47264 (10)	0.216369 (16)	0.16494 (8)	0.05802 (19)
S2	0.95422 (12)	0.21907 (2)	0.98475 (9)	0.0698 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0496 (12)	0.0361 (10)	0.0750 (18)	0.0031 (10)	0.0159 (12)	0.0066 (11)
C2	0.0653 (14)	0.0536 (13)	0.0499 (15)	0.0087 (12)	0.0069 (12)	0.0066 (11)
C3	0.0656 (14)	0.0505 (12)	0.0483 (14)	0.0063 (11)	0.0159 (11)	0.0021 (11)
C4	0.0476 (11)	0.0336 (9)	0.0458 (13)	−0.0015 (9)	0.0138 (9)	0.0020 (8)
C5	0.0664 (14)	0.0486 (12)	0.0450 (14)	0.0081 (11)	0.0160 (11)	0.0053 (10)
C6	0.0465 (11)	0.0424 (11)	0.0580 (15)	−0.0045 (9)	0.0113 (10)	0.0002 (10)
C7	0.0753 (16)	0.0539 (13)	0.0462 (14)	−0.0019 (12)	0.0061 (12)	−0.0049 (11)
C8	0.133 (3)	0.0574 (16)	0.060 (2)	0.0008 (18)	0.0185 (19)	−0.0117 (14)
C9	0.0367 (10)	0.0416 (10)	0.0476 (13)	0.0033 (8)	0.0029 (9)	0.0007 (9)
C10	0.0555 (13)	0.0566 (13)	0.0501 (15)	0.0046 (11)	0.0032 (11)	0.0001 (12)
C11	0.0568 (13)	0.0556 (13)	0.0579 (16)	−0.0027 (11)	0.0177 (12)	−0.0152 (12)
C12	0.0708 (16)	0.0605 (15)	0.0575 (17)	−0.0074 (13)	0.0214 (13)	−0.0025 (12)
C13	0.0601 (14)	0.0736 (16)	0.0541 (16)	−0.0178 (13)	0.0257 (12)	−0.0177 (13)
C14	0.0495 (12)	0.0619 (14)	0.0465 (14)	−0.0090 (11)	0.0106 (10)	−0.0205 (11)
C15	0.0728 (17)	0.0727 (17)	0.0591 (18)	0.0088 (14)	0.0279 (14)	0.0006 (13)
C16	0.0482 (13)	0.0861 (19)	0.0685 (19)	−0.0033 (13)	0.0062 (12)	−0.0297 (15)
C17	0.096 (2)	0.112 (3)	0.0459 (17)	0.009 (2)	0.0141 (15)	0.0145 (17)
C18	0.106 (2)	0.0733 (19)	0.080 (2)	0.0222 (18)	0.0239 (19)	0.0220 (17)
C19	0.0389 (10)	0.0567 (13)	0.0438 (13)	0.0051 (10)	0.0068 (9)	−0.0056 (10)
C20	0.0484 (12)	0.0786 (17)	0.0525 (16)	0.0114 (12)	0.0125 (11)	0.0098 (13)
Cl1	0.0568 (4)	0.0582 (4)	0.1311 (8)	0.0141 (3)	0.0232 (4)	0.0113 (4)
Cl2	0.0785 (5)	0.0756 (5)	0.0938 (6)	0.0180 (4)	0.0307 (4)	−0.0044 (4)
N1	0.0684 (13)	0.0531 (11)	0.0623 (15)	0.0100 (10)	0.0310 (11)	0.0084 (10)
N2	0.0454 (9)	0.0407 (9)	0.0437 (11)	0.0020 (8)	0.0068 (8)	−0.0008 (8)
N3	0.0559 (11)	0.0496 (10)	0.0450 (12)	0.0029 (9)	0.0045 (9)	−0.0002 (9)
N4	0.0968 (18)	0.0831 (17)	0.0537 (15)	0.0063 (14)	0.0119 (13)	0.0126 (13)
N5	0.0701 (14)	0.0680 (13)	0.0662 (15)	0.0064 (11)	0.0349 (12)	−0.0018 (11)
N6	0.0504 (10)	0.0702 (13)	0.0413 (11)	0.0095 (10)	0.0058 (8)	−0.0082 (9)
N7	0.0581 (11)	0.0601 (12)	0.0485 (13)	0.0040 (10)	0.0129 (9)	0.0025 (9)
N8	0.0813 (17)	0.133 (2)	0.0470 (15)	0.0174 (16)	0.0147 (12)	0.0044 (15)
S1	0.0681 (4)	0.0420 (3)	0.0615 (4)	−0.0052 (3)	−0.0003 (3)	0.0019 (3)
S2	0.0892 (5)	0.0566 (4)	0.0649 (5)	0.0004 (3)	0.0145 (4)	−0.0053 (3)

Geometric parameters (Å, º) top

C1—N1	1.314 (3)	C11—N5	1.314 (4)
C1—C2	1.376 (4)	C11—C12	1.375 (4)
C1—Cl1	1.752 (2)	C11—Cl2	1.750 (3)
C2—C3	1.368 (3)	C12—C13	1.383 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.383 (3)	C13—C14	1.378 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.375 (3)	C14—C15	1.373 (4)
C4—C6	1.513 (3)	C14—C16	1.516 (4)
C5—N1	1.340 (3)	C15—N5	1.340 (4)
C5—H5	0.9300	C15—H15	0.9300
C6—N2	1.463 (3)	C16—N6	1.454 (3)
C6—H6A	0.9700	C16—H16A	0.9700
C6—H6B	0.9700	C16—H16B	0.9700
C7—N2	1.451 (3)	C17—N6	1.459 (4)
C7—C8	1.482 (4)	C17—C18	1.461 (5)
C7—H7A	0.9700	C17—H17A	0.9700
C7—H7B	0.9700	C17—H17B	0.9700
C8—S1	1.782 (3)	C18—S2	1.781 (4)
C8—H8A	0.9700	C18—H18A	0.9700
C8—H8B	0.9700	C18—H18B	0.9700
C9—N3	1.312 (3)	C19—N7	1.305 (3)
C9—N2	1.325 (3)	C19—N6	1.331 (3)
C9—S1	1.754 (2)	C19—S2	1.746 (2)
C10—N4	1.152 (3)	C20—N8	1.152 (4)
C10—N3	1.324 (3)	C20—N7	1.321 (3)

N1—C1—C2	125.2 (2)	C14—C13—C12	119.5 (2)
N1—C1—Cl1	115.5 (2)	C14—C13—H13	120.2
C2—C1—Cl1	119.3 (2)	C12—C13—H13	120.2
C3—C2—C1	117.2 (2)	C15—C14—C13	117.3 (2)
C3—C2—H2	121.4	C15—C14—C16	121.5 (3)
C1—C2—H2	121.4	C13—C14—C16	121.1 (3)
C2—C3—C4	120.0 (2)	N5—C15—C14	124.7 (3)
C2—C3—H3	120.0	N5—C15—H15	117.6
C4—C3—H3	120.0	C14—C15—H15	117.6
C5—C4—C3	117.4 (2)	N6—C16—C14	112.62 (19)
C5—C4—C6	120.7 (2)	N6—C16—H16A	109.1
C3—C4—C6	121.9 (2)	C14—C16—H16A	109.1
N1—C5—C4	124.1 (2)	N6—C16—H16B	109.1
N1—C5—H5	118.0	C14—C16—H16B	109.1
C4—C5—H5	118.0	H16A—C16—H16B	107.8
N2—C6—C4	111.60 (17)	N6—C17—C18	109.7 (3)
N2—C6—H6A	109.3	N6—C17—H17A	109.7
C4—C6—H6A	109.3	C18—C17—H17A	109.7
N2—C6—H6B	109.3	N6—C17—H17B	109.7
C4—C6—H6B	109.3	C18—C17—H17B	109.7
H6A—C6—H6B	108.0	H17A—C17—H17B	108.2
N2—C7—C8	108.2 (2)	C17—C18—S2	108.1 (2)
N2—C7—H7A	110.1	C17—C18—H18A	110.1
C8—C7—H7A	110.1	S2—C18—H18A	110.1
N2—C7—H7B	110.1	C17—C18—H18B	110.1
C8—C7—H7B	110.1	S2—C18—H18B	110.1
H7A—C7—H7B	108.4	H18A—C18—H18B	108.4
C7—C8—S1	108.5 (2)	N7—C19—N6	122.2 (2)
C7—C8—H8A	110.0	N7—C19—S2	125.99 (19)
S1—C8—H8A	110.0	N6—C19—S2	111.81 (18)
C7—C8—H8B	110.0	N8—C20—N7	174.3 (3)
S1—C8—H8B	110.0	C1—N1—C5	116.1 (2)
H8A—C8—H8B	108.4	C9—N2—C7	116.01 (19)
N3—C9—N2	122.1 (2)	C9—N2—C6	122.68 (19)
N3—C9—S1	125.52 (18)	C7—N2—C6	120.61 (19)
N2—C9—S1	112.34 (17)	C9—N3—C10	119.3 (2)
N4—C10—N3	174.2 (3)	C11—N5—C15	115.9 (2)
N5—C11—C12	125.0 (2)	C19—N6—C16	121.3 (2)
N5—C11—Cl2	115.7 (2)	C19—N6—C17	115.6 (2)
C12—C11—Cl2	119.3 (2)	C16—N6—C17	122.3 (2)
C11—C12—C13	117.5 (3)	C19—N7—C20	119.1 (2)
C11—C12—H12	121.3	C9—S1—C8	91.61 (12)
C13—C12—H12	121.3	C19—S2—C18	92.62 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N5ⁱ	0.93	2.55	3.459 (4)	167
C13—H13···N1ⁱⁱ	0.93	2.49	3.408 (4)	169

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

Experimental details

Crystal data
Chemical formula	C₁₀H₉ClN₄S
M_r	252.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.1294 (14), 35.469 (7), 9.0211 (18)
β (°)	97.80 (3)
V (Å³)	2260.1 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.50
Crystal size (mm)	0.31 × 0.29 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.863, 0.909
No. of measured, independent and observed [I > 2σ(I)] reflections	21869, 5151, 3505
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.137, 1.08
No. of reflections	5151
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.29

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), 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
C3—H3···N5ⁱ	0.93	2.55	3.459 (4)	167
C13—H13···N1ⁱⁱ	0.93	2.49	3.408 (4)	169

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

Acknowledgements

The authors thank the Special Funds for the Research of Scientific and Technological Innovative Talents of Harbin Municipal Science and Technology Bureau (2009RFXXG027), the Science and Technology Planning Project of Heilongjiang Province (GZ08A401) and Heilongjiang University for supporting this study.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Ishimitsu, K., Suzuki, J., Ohishi, H., Yamada, T., Hatano, R., Takakusa, N. & Mitsui, J. (1991). WO Patent 91/04965. Google Scholar
Maienfisch, P., Haettenschwiler, J., Rindlisbacher, A., Decock, A., Wellmann, H. & Kayser, H. (2003). Chimia, 57, 710–714. CrossRef CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 5| May 2011| Page o1140

doi:10.1107/S1600536811013316

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(Z)-N-{3-[(6-Chloro­pyridin-3-yl)meth­yl]-1,3-thia­zolidin-2-yl­­idene}cyanamide

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