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Volume 69 
Part 8 
Page o1315  
August 2013  

Received 16 July 2013
Accepted 17 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.076
wR = 0.231
Data-to-parameter ratio = 26.0
Details
Open access

2-[1-(2-Hydroxy-4-methoxyphenyl)ethylidene]-N-methylhydrazinecarbothioamide

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, the dihedral angle between the mean planes of the benzene ring and hydrazinecarbothioamide group is 9.2 (1)°. An intramolecular O-H...N hydrogen bond is observed, serving to maintain an approximately planar conformation for the molecule. In the crystal, inversion dimers linked by C-H...O interactions occur. Further C-H...O contacts link dimers into (010) chains.

Related literature

For the synthesis and structure of thiosemicarbazones as ligands, see: Lobana et al. (2009[Lobana, T. S., Sharma, R., Bawa, G. & Khanna, S. (2009). Coord. Chem. Rev. 253, 977-1055.], 2012[Lobana, T. S., Kumari, P., Bawa, G., Hundal, G., Butcher, R. J., Fernandez, F. J., Jasinski, J. P. & Golen, J. A. (2012). Z. Anorg. Allg. Chem. 638, 804-810.]). For palladium complexes with thiosemicarbazone ligands, see: Chellan et al. (2010[Chellan, P., Shunmoogam-Gounden, N., Hendricks, D. T., Gut, J., Rosenthal, P. J., Lategan, C., Smith, P. J., Chibale, K. & Smith, G. S. (2010). Eur. J. Inorg. Chem. pp. 3520-3528.]). For related structures, see: Anderson et al. (2012[Anderson, B. J., Kennedy, C. J. & Jasinski, J. P. (2012). Acta Cryst. E68, o2982.], 2013[Anderson, B. J., Keeler, A. M., O'Rourke, K. A., Krauss, S. T. & Jasinski, J. P. (2013). Acta Cryst. E69, o11.]). For 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

  • Mr = 253.32

  • Monoclinic, P 21 /n

  • a = 10.9881 (8) Å

  • b = 9.1468 (6) Å

  • c = 12.5575 (9) Å

  • [beta] = 109.400 (8)°

  • V = 1190.45 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 173 K

  • 0.42 × 0.38 × 0.14 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.728, Tmax = 1.000

  • 13894 measured reflections

  • 4104 independent reflections

  • 3320 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.076

  • wR(F2) = 0.231

  • S = 1.16

  • 4104 reflections

  • 158 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.21 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.82 1.85 2.566 (3) 145
C10-H10A...O2i 0.96 2.59 3.301 (4) 132
C10-H10C...O1ii 0.96 2.57 3.481 (4) 158
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5331 ).


Acknowledgements

JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, 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., Keeler, A. M., O'Rourke, K. A., Krauss, S. T. & Jasinski, J. P. (2013). Acta Cryst. E69, o11.  [CrossRef] [IUCr Journals]
Anderson, B. J., Kennedy, C. J. & Jasinski, J. P. (2012). Acta Cryst. E68, o2982.  [CSD] [CrossRef] [IUCr Journals]
Chellan, P., Shunmoogam-Gounden, N., Hendricks, D. T., Gut, J., Rosenthal, P. J., Lategan, C., Smith, P. J., Chibale, K. & Smith, G. S. (2010). Eur. J. Inorg. Chem. pp. 3520-3528.  [Web of Science] [CSD] [CrossRef]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Lobana, T. S., Kumari, P., Bawa, G., Hundal, G., Butcher, R. J., Fernandez, F. J., Jasinski, J. P. & Golen, J. A. (2012). Z. Anorg. Allg. Chem. 638, 804-810.  [CSD] [CrossRef] [ChemPort]
Lobana, T. S., Sharma, R., Bawa, G. & Khanna, S. (2009). Coord. Chem. Rev. 253, 977-1055.  [Web of Science] [CrossRef] [ChemPort]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1315  [ doi:10.1107/S1600536813019831 ]

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