2-Cyclo­hexyl­idene-N-methyl­hydrazine­carbothio­amide

Tayamon, S.; Mazlan, N.A.; Ravoof, T.B.S.A.; Mohamed Tahir, M.I.; Crouse, K.A.

doi:10.1107/S1600536812042018

Volume 68
Part 11
Pages o3104-o3105
November 2012

Received 30 July 2012
Accepted 8 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.090
Data-to-parameter ratio = 17.2
Details

2-Cyclohexylidene-N-methylhydrazinecarbothioamide

Shahedeh Tayamon,^a Nurul Ain Mazlan,^a Thahira Begum S. A. Ravoof,^a ^* Mohamed Ibrahim Mohamed Tahir ^a and Karen A Crouse ^a

^aDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia.
Correspondence e-mail: thahira.begum@science.upm.edu.my

The title compound C₈H₁₅N₃S has two molecules in the asymmetric unit in which cis-trans isomerism is exhibited around the N(NH)C=S bonds. The cyclohexyl rings in both molecules adopt a chair conformation. In the crystal, N-HS hydrogen bonding produces dimers, which are interconnected through further N-HS hydrogen bonds, forming chains along the b-axis direction.

Related literature

For background to the coordination chemistry of dithiocarbazate derivatives, see: Zhang et al. (2011); Khoo et al. (2005); Ravoof et al. (2010). For the synthesis and methodology, see: Tian et al. (1997); Tarafder et al. (2000); Tan et al. (2012). For related structures, see: Paulus et al. (2011); Tayamon et al. (2012). For packing arrangements in other cyclohexyl compounds, see: Rohr et al. (2009). For riding constrints, see: Cooper et al. (2010). For charge delocalization, see: Sanderson (1967). For the synthesis, see: Tian et al. (1997).

Experimental

Crystal data

C₈H₁₅N₃S
M_r = 185.29
Monoclinic, P 2₁ /c
a = 10.0538 (3) Å
b = 11.0108 (3) Å
c = 17.9484 (5) Å
= 102.132 (3)°
V = 1942.52 (10) Å³
Z = 8
Cu K radiation
= 2.56 mm^-1
T = 100 K
0.27 × 0.22 × 0.10 mm

Data collection

Agilent Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) T_min = 0.58, T_max = 0.77
13859 measured reflections
3754 independent reflections
3414 reflections with I > 2.0(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.090
S = 0.98
3740 reflections
217 parameters
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N205-H2051S101ⁱ	0.89	2.57	3.4559 (13)	175
N105-H1051S201ⁱⁱ	0.87	2.59	3.4484 (13)	169
N203-H2031S201ⁱⁱ	0.87	2.76	3.4691 (13)	139
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2476 ).

Acknowledgements

Support for this project came from Universiti Putra Malaysia (UPM) under their Research University Grant Scheme (RUGS No. 05-01-11-1243RU) and the Malaysian Fundamental Research Grant Scheme (FRGS No. 01-13-11-986FR). We also thank Siti Khadijah Densabali for collecting the X-ray data. ST and NAM wish to acknowledge the Malaysian Government for sponsorship under the FRGS/RUGS Scheme.

References

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organic compounds