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Volume 69 
Part 7 
Page o1147  
July 2013  

Received 20 May 2013
Accepted 19 June 2013
Online 22 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.049
wR = 0.171
Data-to-parameter ratio = 13.9
Details
Open access

1,5-Bis(2-methoxybenzylidene)thiocarbonohydrazide methanol monosolvate

aDepartment of Chemistry, College of Science, China University of Petroleum, Qingdao 266555, People's Republic of China, and bSate Key Laboratory of Heavy Oil Processing, China University of Petroleum, Qingdao 266555, People's Republic of China
Correspondence e-mail: zfyancat@163.com

The title compound, C17H18N4O2S·CH3OH, was synthesized by the condensation reaction of o-methoxybenzaldehyde with thiocarbohydrazide in methanol. The two benzene rings are inclined each to other at 31.7 (1)°. Intermolecular N-H...O and bifurcated O-H...N(S) hydrogen bonds link two thiocarbonohydrazide and two solvent molecules into a centrosymmetric unit. These units, related by translation along the b axis, are further aggregated into columns through N-H...S hydrogen bonds.

Related literature

For biological activities of thiocarbohydrazides, see: Liang (2003[Liang, F.-Z. (2003). J. Shandong Normal Univ. (Nat. Sci.), 18, 50-51.]); Bacchi et al. (2005[Bacchi, A., Carcelli, M., Pelagatti, P., Pelizzi, G., Rodriguez-Arguelles, M. C., Rogolino, D., Solinas, C. & Zani, F. (2005). J. Inorg. Biochem. 99, 397-408.]). For the crystal structures of related compounds, see: Fang et al. (2006[Fang, X.-N., Xu, Y.-P., Guo, X.-F. & Zeng, X.-R. (2006). Acta Cryst. E62, o1052-o1054.]); Feng et al. (2011[Feng, L., Ji, H., Wang, R., Ge, H. & Li, L. (2011). Acta Cryst. E67, o1514.]); Zhao (2011[Zhao, X. (2011). Acta Cryst. E67, o2133.]).

[Scheme 1]

Experimental

Crystal data
  • C17H18N4O2S·CH4O

  • Mr = 374.46

  • Triclinic, [P \overline 1]

  • a = 7.7223 (15) Å

  • b = 10.232 (2) Å

  • c = 12.648 (3) Å

  • [alpha] = 85.938 (3)°

  • [beta] = 80.796 (3)°

  • [gamma] = 79.550 (3)°

  • V = 969.3 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 296 K

  • 0.25 × 0.21 × 0.18 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.954, Tmax = 0.966

  • 4769 measured reflections

  • 3324 independent reflections

  • 2766 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.171

  • S = 1.01

  • 3324 reflections

  • 240 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 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
O3-H3...S1i 0.82 2.80 3.534 (2) 150
O3-H3...N4i 0.82 2.36 3.028 (3) 139
N3-H3A...O3 0.86 2.38 3.126 (3) 145
N1-H1...S1ii 0.86 2.57 3.4184 (19) 169
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+2, -z.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: CV5415 ).


Acknowledgements

The authors gratefully acknowledge the financial support of the Fundamental Research Funds for the Central Universities (grant No. 12CX04091A).

References

Bacchi, A., Carcelli, M., Pelagatti, P., Pelizzi, G., Rodriguez-Arguelles, M. C., Rogolino, D., Solinas, C. & Zani, F. (2005). J. Inorg. Biochem. 99, 397-408.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fang, X.-N., Xu, Y.-P., Guo, X.-F. & Zeng, X.-R. (2006). Acta Cryst. E62, o1052-o1054.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Feng, L., Ji, H., Wang, R., Ge, H. & Li, L. (2011). Acta Cryst. E67, o1514.  [CSD] [CrossRef] [IUCr Journals]
Liang, F.-Z. (2003). J. Shandong Normal Univ. (Nat. Sci.), 18, 50-51.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Zhao, X. (2011). Acta Cryst. E67, o2133.  [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1147  [ doi:10.1107/S1600536813016954 ]

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