Benzaldehyde thio­semicarbazone

Kong, L.; Qiao, Y.; Zhang, J.-D.; Ju, X.-P.

doi:10.1107/S1600536808038270

Volume 64
Part 12
Page o2412
December 2008

Received 5 October 2008
Accepted 17 November 2008
Online 22 November 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.007 Å
R = 0.058
wR = 0.162
Data-to-parameter ratio = 14.4
Details

Benzaldehyde thiosemicarbazone

Lingqian Kong,^a ^* Yan Qiao,^a Ji-Dong Zhang ^a and Xiu-Ping Ju ^a

^aDongchang College, Liaocheng University, Liaocheng 250059, People's Republic of China
Correspondence e-mail: konglingqian08@163.com

The title compound, C₈H₉N₃S, contains two molecules in the asymmetric unit. One molecule is close to being planar (r.m.s. deviation from the mean plane = 0.06 Å for the non-H atoms), while the other exhibits a dihedral angle of 21.7 (1)° between the benzene ring and the mean plane of the thiosemicarbazone unit. Intermolecular N-HS hydrogen bonds link the molecules into layers parallel to the (010) plane.

Related literature

For background literature concerning arylhydrazone compounds, see: Beraldo & Gambino (2004); Bondock et al. (2007). For the related 2,4-dichlorobenzylidene compound, see: Jing et al. (2006).

Experimental

Crystal data

C₈H₉N₃S
M_r = 179.24
Triclinic, $[P \overline 1]$
a = 5.8692 (13) Å
b = 12.513 (2) Å
c = 13.519 (2) Å
= 112.735 (3)°
= 95.384 (2)°
= 96.153 (2)°
V = 900.4 (3) Å³
Z = 4
Mo K radiation
= 0.31 mm^-1
T = 298 (2) K
0.24 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.930, T_max = 0.970
4740 measured reflections
3124 independent reflections
1846 reflections with I > 2(I)
R_int = 0.039

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.162
S = 0.95
3124 reflections
217 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2S1ⁱ	0.86	2.64	3.443 (3)	155
N3-H3AS1ⁱⁱ	0.86	2.98	3.488 (3)	120
N5-H5S1ⁱⁱ	0.86	2.61	3.441 (3)	162
N6-H6BS2ⁱⁱⁱ	0.86	2.51	3.368 (3)	173
Symmetry codes: (i) -x+3, -y+2, -z+2; (ii) x-1, y, z; (iii) -x+2, -y+2, -z+1.

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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: BI2310 ).

Acknowledgements

This project was supported by the Foundation of Dongchang College, Liaocheng University (grant No. DCLG2008002).

References

Beraldo, H. & Gambino, D. (2004). Mini Rev. Med. Chem. 4, 31-39.
Bondock, S., Khalifa, W. & Fadda, A. A. (2007). Eur. J. Med. Chem. 42, 948-954.
Jing, Z.-L., Zhang, Q.-Z., Yu, M. & Chen, X. (2006). Acta Cryst. E62, o4489-o4490.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

organic compounds