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

Anderson, B.J.; Keeler, A.M.; O'Rourke, K.A.; Krauss, S.T.; Jasinski, J.P.

doi:10.1107/S1600536812048799

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 (C-C) = 0.003 Å
R = 0.063
wR = 0.170
Data-to-parameter ratio = 16.0
Details

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

Brian J. Anderson,^a Alexander M. Keeler,^a Kelly A. O'Rourke,^a Shannon T. Krauss ^a and Jerry P. Jasinski ^a ^*

^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-HN hydrogen bond while O-HS hydrogen bonds link the molecules into columns along [100].

Related literature

For thiosemicarbazone structures and their biological activity, see: Lobana et al. (2009). For thiosemicarbazone as ligands for hydrogenations or metal-catalysed reactions, see: Pelagatti et al. (1998); Xie et al. (2010). For a related structure, see: Anderson et al. (2012). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₁₁H₁₅N₃O₂S·C₂H₃N
M_r = 294.38
Triclinic, $[P \overline 1]$
a = 7.6232 (10) Å
b = 9.4004 (9) Å
c = 11.8031 (12) Å
= 80.121 (8)°
= 71.555 (10)°
= 74.732 (10)°
V = 770.44 (16) Å³
Z = 2
Cu K radiation
= 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) T_min = 0.575, T_max = 1.000
4716 measured reflections
2968 independent reflections
2622 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.063
wR(F²) = 0.170
S = 1.06
2968 reflections
186 parameters
H-atom parameters constrained
_max = 1.13 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2S1ⁱ	0.84	2.34	3.1823 (17)	177
N1-H1N1A	0.88	2.25	3.039 (3)	149
Symmetry code: (i) -x, -y+2, -z+2.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Lobana, T. S., Sharma, R., Bawa, G. & Khanna, S. (2009). Coord. Chem. Rev. 253, 977-1055.
Pelagatti, P., Venturini, A., Carcelli, M., Costa, M., Bacchi, A., Pelizzi, G. & Pelizza, C. (1998). J. Chem. Soc. Dalton Trans. pp. 2715-2721.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Xie, G., Chellan, P., Mao, J., Chibale, K. & Smith, G. S. (2010). Adv. Synth. Catal. 352, 1641-1647.

organic compounds