N′-[3-(Hy­droxy­imino)­butan-2-yl­idene]-4-methyl­benzene-1-sulfono­hydrazide

Bulhosa, M.C.S.; Gervini, V.C.; Bresolin, L.; Locatelli, A.; Oliveira, A.B. de

doi:10.1107/S1600536812003339

Volume 68
Part 3
Page o592
March 2012

Received 17 January 2012
Accepted 26 January 2012
Online 4 February 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.112
Data-to-parameter ratio = 18.5
Details

N'-[3-(Hydroxyimino)butan-2-ylidene]-4-methylbenzene-1-sulfonohydrazide

Maria C. S. Bulhosa,^a Vanessa Carratu Gervini,^a ^* Leandro Bresolin,^a Aline Locatelli ^b and Adriano Bof de Oliveira ^c

^aEscola de Química e Alimentos, Universidade Federal do Rio Grande, Av. Itália km 08, Campus Carreiros, 96201-900, Rio Grande, RS, Brazil,^bDepartamento de Química, Universidade Federal de Santa Maria, Av. Roraima, Campus, 97105-900, Santa Maria, RS, Brazil, and ^cDepartamento de Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, Campus, 49100-000, São Cristóvão, SE, Brazil
Correspondence e-mail: adriano@daad-alumni.de

In the title compound, C₁₁H₁₅N₃O₃S, the C-S-N(H)-N linkage is nonplanar, the torsion angle being 75.70 (12)°. The compound has two almost planar fragments linked to the S atom: the hydrazone-derivative fragment [(HONC₄H₆)N-N(H)-] and the tolyl fragment (C₇H₇-) have maximum deviations from the mean plane through the non-H atoms of 0.0260 (10) and 0.0148 (14) Å, respectively. The two planar fragments make an interplanar angle of 79.47 (5)°. In the crystal, molecules are connected through inversion centers via pairs of N-HO and O-HN hydrogen bonds.

Related literature

For the synthesis and application of hydroxyimino-tosylhydrazones as complexing agents, see: Beger et al. (1991). For a similar structure with a tosylhydrazone derivative, see: Fonseca et al. (2011).

Experimental

Crystal data

C₁₁H₁₅N₃O₃S
M_r = 269.32
Triclinic, $[P \overline 1]$
a = 5.5740 (1) Å
b = 10.4354 (2) Å
c = 11.3997 (2) Å
= 83.586 (1)°
= 77.453 (1)°
= 87.688 (1)°
V = 643.11 (2) Å³
Z = 2
Mo K radiation
= 0.26 mm^-1
T = 293 K
0.55 × 0.24 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.872, T_max = 0.946
11000 measured reflections
3211 independent reflections
2862 reflections with I > 2(I)
R_int = 0.015

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.112
S = 1.05
3211 reflections
174 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.27 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H8O3ⁱ	0.82 (2)	2.19 (2)	2.9830 (18)	165.0 (19)
O1-H1N1ⁱⁱ	0.84 (3)	1.99 (3)	2.792 (2)	160 (2)
Symmetry codes: (i) -x+2, -y, -z; (ii) -x, -y+1, -z.

Data collection: COSMO (Bruker, 2005); cell refinement: SAINT; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); 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: FY2042 ).

Acknowledgements

The authors gratefully acknowledge Professor Dr Manfredo Hörner (Department of Chemistry, Federal University of Santa Maria, Brazil) for his help and support with the X-ray measurements, and CNPq/FAPERGS for financial support.

References

Beger, J., Siedler, F., Mühl, P. & Gloe, K. (1991). German Patent DD287027A5.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2005). COSMO, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fonseca, A. de S., Storino, T. G., Carratu, V. S., Locatelli, A. & Oliveira, A. B. de (2011). Acta Cryst. E67, o3256.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds