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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 [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.090
Data-to-parameter ratio = 17.2
Details
Open access

2-Cyclohexylidene-N-methylhydrazinecarbothioamide

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-H...S hydrogen bonding produces dimers, which are interconnected through further N-H...S 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[Zhang, H. J., Qian, Y., Zhu, D. D., Yang, X. G. & Zhu, H. L. (2011). Eur. J. Med. Chem. 46, 4702-4708.]); Khoo et al. (2005[Khoo, T.-J., Cowley, A. R., Watkin, D. J., Crouse, K. A. & Tarafder, M. T. H. (2005). Acta Cryst. E61, o2441-o2443.]); Ravoof et al. (2010[Ravoof, T. B. S. A., Crouse, K. A., Tahir, M. I. M., How, F. N. F., Rosli, R. & Watkins, D. J. (2010). Transition Met. Chem. 35, 871-876.]). For the synthesis and methodology, see: Tian et al. (1997); Tarafder et al. (2000[Tarafder, M. T. A., Ali, M. A., Wee, D. J., Azahari, K., Silong, S. & Crouse, K. A. (2000). Transition Met. Chem, 25, 456-460.]); Tan et al. (2012[Tan, M.-Y., Ravoof, T. B. S. A., Tahir, M. I. M., Crouse, K. A. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o1461-o1462.]). For related structures, see: Paulus et al. (2011[Paulus, G., Crouse, K. A., Mohamed Tahir, M. I. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o1370-o1371.]); Tayamon et al. (2012[Tayamon, S., Ravoof, T. B. S. A., Tahir, M. I. M., Crouse, K. A. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o1640-o1641.]). For packing arrangements in other cyclohexyl compounds, see: Rohr et al. (2009[Rohr, K., Herre, R. & Mahrwald, R. (2009). J. Org. Chem. 74, 3744-3749.]). For riding constrints, see: Cooper et al. (2010[Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 43, 1100-1107.]). For charge delocalization, see: Sanderson (1967[Sanderson, R. T. (1967). Inorganic Chemistry, 1st edition. New York: Reinhold.]). For the synthesis, see: Tian et al. (1997[Tian, Y.-P., Duan, C.-Y., Zhao, C.-Y., You, X.-Z., Mak, T. C. W. & Zhang, Z.-Y. (1997). Inorg. Chem. 36, 1247-1252.]).

[Scheme 1]

Experimental

Crystal data
  • C8H15N3S

  • Mr = 185.29

  • Monoclinic, P 21 /c

  • a = 10.0538 (3) Å

  • b = 11.0108 (3) Å

  • c = 17.9484 (5) Å

  • [beta] = 102.132 (3)°

  • V = 1942.52 (10) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 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[Agilent, (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.58, Tmax = 0.77

  • 13859 measured reflections

  • 3754 independent reflections

  • 3414 reflections with I > 2.0[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.090

  • S = 0.98

  • 3740 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N205-H2051...S101i 0.89 2.57 3.4559 (13) 175
N105-H1051...S201ii 0.87 2.59 3.4484 (13) 169
N203-H2031...S201ii 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[Agilent, (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, UK.]); 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

Agilent, (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  [CrossRef] [details]
Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 43, 1100-1107.  [ISI] [CrossRef] [ChemPort] [details]
Khoo, T.-J., Cowley, A. R., Watkin, D. J., Crouse, K. A. & Tarafder, M. T. H. (2005). Acta Cryst. E61, o2441-o2443.  [CSD] [CrossRef] [details]
Paulus, G., Crouse, K. A., Mohamed Tahir, M. I. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o1370-o1371.  [CSD] [CrossRef] [details]
Ravoof, T. B. S. A., Crouse, K. A., Tahir, M. I. M., How, F. N. F., Rosli, R. & Watkins, D. J. (2010). Transition Met. Chem. 35, 871-876.  [ISI] [CSD] [CrossRef] [ChemPort]
Rohr, K., Herre, R. & Mahrwald, R. (2009). J. Org. Chem. 74, 3744-3749.  [CSD] [CrossRef] [PubMed] [ChemPort]
Sanderson, R. T. (1967). Inorganic Chemistry, 1st edition. New York: Reinhold.
Tan, M.-Y., Ravoof, T. B. S. A., Tahir, M. I. M., Crouse, K. A. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o1461-o1462.  [CSD] [CrossRef] [details]
Tarafder, M. T. A., Ali, M. A., Wee, D. J., Azahari, K., Silong, S. & Crouse, K. A. (2000). Transition Met. Chem, 25, 456-460.  [ISI] [CrossRef] [ChemPort]
Tayamon, S., Ravoof, T. B. S. A., Tahir, M. I. M., Crouse, K. A. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o1640-o1641.  [CSD] [CrossRef] [details]
Tian, Y.-P., Duan, C.-Y., Zhao, C.-Y., You, X.-Z., Mak, T. C. W. & Zhang, Z.-Y. (1997). Inorg. Chem. 36, 1247-1252.  [CrossRef] [PubMed] [ChemPort] [ISI]
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, UK.
Zhang, H. J., Qian, Y., Zhu, D. D., Yang, X. G. & Zhu, H. L. (2011). Eur. J. Med. Chem. 46, 4702-4708.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o3104-o3105   [ doi:10.1107/S1600536812042018 ]

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