2,4-Dichloro­benzaldehyde 4-methyl­thio­semicarbazone

Li, R.

doi:10.1107/S1600536810049743

Volume 67
Part 1
Page o20
January 2011

Received 28 November 2010
Accepted 29 November 2010
Online 4 December 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.037
wR = 0.092
Data-to-parameter ratio = 17.6
Details

2,4-Dichlorobenzaldehyde 4-methylthiosemicarbazone

Rongchun Li ^a ^*

^aDepartment of Chemistry, Dezhou University, Dezhou 253023, People's Republic of China
Correspondence e-mail: rongchunli01@126.com

The molecule of the title compound, C₉H₉Cl₂N₃S, has an E configuration about the C=N bond. In the crystal, molecules are linked through intermolecular N-HS hydrogen bonds, forming zigzag chains along the a axis.

Related literature

For background to Schiff bases derived from thiosemicarbazone and its derivatives, see: Casas et al. (2001); Beraldo et al. (2001); Jouad et al. (2002); Swearingen et al. (2002). For a similar structure reported recently by the author, see: Li (2010). For bond-length data, see: Allen et al. (1987). For similar structures, see: Selvanayagam et al. (2002); Karakurt et al. (2003); Bernhardt et al. (2003); Sampath et al. (2003).

Experimental

Crystal data

C₉H₉Cl₂N₃S
M_r = 262.15
Monoclinic, C 2/c
a = 13.444 (3) Å
b = 9.3299 (19) Å
c = 18.499 (4) Å
= 92.160 (2)°
V = 2318.7 (8) Å³
Z = 8
Mo K radiation
= 0.71 mm^-1
T = 298 K
0.18 × 0.17 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) T_min = 0.883, T_max = 0.913
7167 measured reflections
2518 independent reflections
1956 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.092
S = 1.05
2518 reflections
143 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.23 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2S1ⁱ	0.90 (1)	2.54 (1)	3.4169 (18)	167 (2)
N3-H3S1ⁱⁱ	0.89 (1)	2.77 (2)	3.491 (2)	139 (2)
Symmetry codes: (i) $[-x, y, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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: HG2763 ).

References

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.
Beraldo, H., Lima, R., Teixeira, L. R., Moura, A. A. & West, D. X. (2001). J. Mol. Struct. 559, 99-106.
Bernhardt, P. V., Caldwell, L. M., Lovejoy, D. B. & Richardson, D. R. (2003). Acta Cryst. C59, o629-o633.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Casas, J. S., Castineiras, A., Lobana, T. S., Sanchez, A., Sordo, J. & Garcia-Tasende, M. S. (2001). J. Chem. Crystallogr. 31, 329-332.
Jouad, E. M., Allain, M., Khan, M. A. & Bouet, G. M. (2002). J. Mol. Struct. 604, 205-209.
Karakurt, T., Dinçer, M., Yilmaz, I. & Çukurovali, A. (2003). Acta Cryst. E59, o1997-o1999.
Li, R. (2010). Acta Cryst. E66, o3324.
Sampath, N., Malathy Sony, S. M., Ponnuswamy, M. N. & Nethaji, M. (2003). Acta Cryst. C59, o346-o348.
Selvanayagam, S., Yogavel, M., Rajakannan, V., Velmurugan, D., Shanmuga Sundara Raj, S. & Fun, H.-K. (2002). Acta Cryst. E58, o1336-o1338.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Swearingen, J. K., Kaminsky, W. & West, D. X. (2002). Transition Met. Chem. 27, 724-731.

organic compounds