1,5-Bis[(E)-cyclo­pentyl­idene]thio­carbono­hydrazide

Qingliang Guo; Junshan Sun; Jikun Li; Rentao Wu; Wenzeng Duan

doi:10.1107/S1600536809009325

. 2009 Mar 25;65(Pt 4):o818. doi: 10.1107/S1600536809009325

1,5-Bis[(E)-cyclopentylidene]thiocarbonohydrazide

Qingliang Guo ^a,^*, Junshan Sun ^b, Jikun Li ^b, Rentao Wu ^a, Wenzeng Duan ^a

PMCID: PMC2969008 PMID: 21582539

Abstract

In the title molecule, C₁₁H₁₈N₄S, an intramolecular N—H⋯N hydrogen bond [N⋯N = 2.558 (3)Å] is observed. The two cyclopentyl rings are disordered between two conformations in 1:1 and 2:1 ratios. In the crystal structure, weak intermolecular N—H⋯S hydrogen bonds [N⋯S = 3.547 (3) Å] link pairs of molecules into centrosymmetric dimers.

Related literature

For related Schiff base derivatives of thiocarbohydrazide, see: Bacchi et al. (1996 ▶); Chantrapromma et al. (2001 ▶).

Experimental

Crystal data

C₁₁H₁₈N₄S
M _r = 238.35
Triclinic,
a = 6.0344 (19) Å
b = 10.114 (3) Å
c = 11.137 (3) Å
α = 106.579 (5)°
β = 96.897 (5)°
γ = 100.574 (5)°
V = 629.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 273 K
0.12 × 0.08 × 0.06 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.972, T _max = 0.986
3340 measured reflections
2212 independent reflections
1673 reflections with I > 2σ(I)
R _int = 0.013

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.112
S = 1.03
2212 reflections
172 parameters
53 restraints
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶) ; cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT (Siemens, 1996 ▶); 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 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009325/cv2503sup1.cif

e-65-0o818-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009325/cv2503Isup2.hkl

e-65-0o818-Isup2.hkl^{(108.7KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N2	0.86	2.17	2.558 (3)	108
N1—H1⋯S1ⁱ	0.86	2.70	3.547 (3)	170

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Postgraduate Foundation of Taishan University for financial support (grant No. Y06-2-10).

supplementary crystallographic information

Comment

Thiocarbohydrazide and its Schiff base derivatives have attracted considerable interest in the chemistry of metal complexes containing nitrogen and donors (Bacchi et al., 1996; Chantrapromma et al., 2001]. The interest in this field may be attributed to the striking structural features in the resultant metal complexes and their biological activities. Herein we present the synthesis and crystal structure of the title compound.

The title compound is shown in Fig. 1. Two cyclopentanone rings are disordered between two conformations in the ratios 1:1 and 2:1, respectively. The four N atoms and the C═S are almost coplanar with the mean deviation of 0.024 (2) Å. In this molecule, there exist intramolecular N—H···N hydrogen bond (Table 1). Weak intermolecular N—H···S hydrogen bonds (Table 1) link two molecules into centrosymmetric dimers.

Experimental

A solution of cyclopentanone and thiocarbohydrazide in ethanol in the ratio of 2:1 were refluxed for 8 h with stirring and cooled to the room temperature. The yellow precipitated powder of title compound was filtered and washed with water and ethanol, and then air dried thoroughly. A crystal suitable for X-ray diffraction was obtained by evaporation from a DMF and ethanol mixture. The yield is 78% and elemental analysis: calc. for C₁₁H₁₈N₄S: C 55.43, H 7.61, N 23.51; found: C 55.26, H 7.49, N 23.88%. The elemental analyses were performed with PERKIN ELMER MODEL 2400 SERIES II. The CCDC number: 695533.