1-(4-Meth­oxy­benzyl­idene)-4-methyl­thiosemicarbazide

Li, Y.-F.

doi:10.1107/S1600536810038882

Volume 66
Part 11
Page o2728
November 2010

Received 27 September 2010
Accepted 29 September 2010
Online 9 October 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.040
wR = 0.146
Data-to-parameter ratio = 19.3
Details

1-(4-Methoxybenzylidene)-4-methylthiosemicarbazide

Yu-Feng Li ^a ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
Correspondence e-mail: liyufeng8111@163.com

The title compound, C₁₀H₁₃N₃OS, was prepared by the reaction of 4-methoxybenzaldehyde and 4-methylthiosemicarbazide. The dihedral angle between the benzene ring and the thiourea unit is 8.64 (7)° and an intramolecular N-HN hydrogen bond generates an S(5) ring. In the crystal, inversion dimers linked by pairs of N-HS hydrogen bonds generate R₂²(8) loops. The dimers are linked into (001) sheets by further N-HS links.

Related literature

For background to Schiff bases, see: Casas et al. (2000). For a related structure, see: Li & Jian (2010).

Experimental

Crystal data

C₁₀H₁₃N₃OS
M_r = 223.29
Orthorhombic, P b c a
a = 13.397 (3) Å
b = 9.1271 (18) Å
c = 18.799 (4) Å
V = 2298.6 (8) Å³
Z = 8
Mo K radiation
= 0.26 mm^-1
T = 293 K
0.25 × 0.22 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
20742 measured reflections
2627 independent reflections
1746 reflections with I > 2(I)
R_int = 0.061

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.146
S = 0.94
2627 reflections
136 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AN3	0.86	2.28	2.661 (2)	107
N1-H1AS1ⁱ	0.86	2.86	3.4718 (18)	130
N2-H2AS1ⁱⁱ	0.86	2.59	3.4359 (17)	169
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) -x+2, -y+2, -z+1.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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: HB5659 ).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Casas, J. S., Garcia-T, M. S. & Sordo, J. (2000). Coord. Chem. Rev. 209, 197-261.
Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o1399.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds