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Volume 69 
Part 1 
Page o11  
January 2013  

Received 20 November 2012
Accepted 27 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.063
wR = 0.170
Data-to-parameter ratio = 16.0
Details
Open access

2-[1-(2-Hydroxy-6-methoxyphenyl)ethylidene]-N-methylhydrazinecarbothioamide acetonitrile monosolvate

aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C11H15N3O2S·C2H3N, the dihedral angle between the benzene ring and the mean plane of the hydrazinecarbothioamide group is 75.1 (2)°. In the crystal, the main molecule is linked to the solvent molecule by a weak N-H...N hydrogen bond while O-H...S hydrogen bonds link the molecules into columns along [100].

Related literature

For thiosemicarbazone structures and their biological activity, see: Lobana et al. (2009[Lobana, T. S., Sharma, R., Bawa, G. & Khanna, S. (2009). Coord. Chem. Rev. 253, 977-1055.]). For thiosemicarbazone as ligands for hydrogenations or metal-catalysed reactions, see: Pelagatti et al. (1998[Pelagatti, P., Venturini, A., Carcelli, M., Costa, M., Bacchi, A., Pelizzi, G. & Pelizza, C. (1998). J. Chem. Soc. Dalton Trans. pp. 2715-2721.]); Xie et al. (2010[Xie, G., Chellan, P., Mao, J., Chibale, K. & Smith, G. S. (2010). Adv. Synth. Catal. 352, 1641-1647.]). For a related structure, see: Anderson et al. (2012[Anderson, B. J., Kennedy, C. J. & Jasinski, J. P. (2012). Acta Cryst. E68, o2982.]). For standard bond lengths, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C11H15N3O2S·C2H3N

  • Mr = 294.38

  • Triclinic, [P \overline 1]

  • a = 7.6232 (10) Å

  • b = 9.4004 (9) Å

  • c = 11.8031 (12) Å

  • [alpha] = 80.121 (8)°

  • [beta] = 71.555 (10)°

  • [gamma] = 74.732 (10)°

  • V = 770.44 (16) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 1.93 mm-1

  • T = 173 K

  • 0.44 × 0.28 × 0.12 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini CCD) diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.]) Tmin = 0.575, Tmax = 1.000

  • 4716 measured reflections

  • 2968 independent reflections

  • 2622 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.063

  • wR(F2) = 0.170

  • S = 1.06

  • 2968 reflections

  • 186 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.13 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...S1i 0.84 2.34 3.1823 (17) 177
N1-H1...N1A 0.88 2.25 3.039 (3) 149
Symmetry code: (i) -x, -y+2, -z+2.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2388 ).


Acknowledgements

JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.
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.
Anderson, B. J., Kennedy, C. J. & Jasinski, J. P. (2012). Acta Cryst. E68, o2982.  [CSD] [CrossRef] [details]
Lobana, T. S., Sharma, R., Bawa, G. & Khanna, S. (2009). Coord. Chem. Rev. 253, 977-1055.  [ISI] [CrossRef] [ChemPort]
Pelagatti, P., Venturini, A., Carcelli, M., Costa, M., Bacchi, A., Pelizzi, G. & Pelizza, C. (1998). J. Chem. Soc. Dalton Trans. pp. 2715-2721.  [CSD] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Xie, G., Chellan, P., Mao, J., Chibale, K. & Smith, G. S. (2010). Adv. Synth. Catal. 352, 1641-1647.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o11  [ doi:10.1107/S1600536812048799 ]

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