(E)-N′-(9-Anthryl­methyl­idene)-p-toluene­sulfono­hydrazide

Asiri, A.M.; Zayed, M.E.M.; Ng, S.W.

doi:10.1107/S160053681003271X

Volume 66
Part 9
Page o2361
September 2010

Received 12 August 2010
Accepted 14 August 2010
Online 21 August 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.040
wR = 0.104
Data-to-parameter ratio = 16.9
Details

(E)-N'-(9-Anthrylmethylidene)-p-toluenesulfonohydrazide

Abdullah M. Asiri,^a Mohie E. M. Zayed ^a and Seik Weng Ng ^b ^*

^aChemistry Department, Faculty of Science, King Abdul Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The S-N(H)-N=C linkage in the title molecule, C₂₂H₁₈N₂O₂S, is non-planar [torsion angle = 30.6 (1)°] as the amino N atom is pyramidally coordinated. In the crystal, the amino group acts as a hydrogen-bond donor to an O atom of an adjacent molecule, generating chains running parallel to the b axis.

Related literature

For the structure of the (E)-N'-benzylidene-p-toluenesulfonohydrazide analog, see: Mehrabi et al. (2008).

Experimental

Crystal data

C₂₂H₁₈N₂O₂S
M_r = 374.44
Orthorhombic, P b c a
a = 17.3634 (15) Å
b = 9.2438 (8) Å
c = 22.882 (2) Å
V = 3672.6 (6) Å³
Z = 8
Mo K radiation
= 0.20 mm^-1
T = 100 K
0.40 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.926, T_max = 0.990
22220 measured reflections
4209 independent reflections
3158 reflections with I > 2(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.104
S = 1.02
4209 reflections
249 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.34 e Å^-3
_min = -0.46 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.86 (1)	2.07 (1)	2.911 (2)	169 (2)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2262 ).

Acknowledgements

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Mehrabi, H., Kia, R., Hassanzadeh, A., Ghobadi, S. & Khavasi, H. R. (2008). Acta Cryst. E64, o1845.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds