N′-(4-Bromo­benzyl­idene)quinoline-8-sulfonohydrazide

Oliveira, K.N. de; Nunes, R.J.; Foro, S.

doi:10.1107/S1600536809008848

Volume 65
Part 4
Page o779
April 2009

Received 31 October 2008
Accepted 10 March 2009
Online 19 March 2009

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.006 Å
R = 0.052
wR = 0.147
Data-to-parameter ratio = 13.9
Details

N'-(4-Bromobenzylidene)quinoline-8-sulfonohydrazide

Kely Navakoski de Oliveira,^a Ricardo José Nunes ^a and Sabine Foro ^b ^*

^aDepartamento de Química-UFSC, 88040-900 Florianópolis, SC, Brazil, and ^bClemens Schöpf-Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Petersenstrasse 22, D-64287 Darmstadt, Germany
Correspondence e-mail: kely_navakoski@yahoo.com.br

In the title compound, C₁₆H₁₂BrN₃O₂S, the dihedral angle between the planes of the almost planar (r.m.s. deviation = 0.0263 Å) quinoline group and the bromophenyl group is 87.4 (1)°. The torsion angle of the central S-N-N-C bridge is 144.8 (2)°. The amino group has an intramolecular contact to the quinoline N atom. The structure is stabilized by one N-HO and two C-HO intermolecular hydrogen bonds.

Related literature

For general background, see: Dueñas-Romero et al. (2006); da Silva et al. (2007). For related compounds, see: Oliveira & Nunes (2006); Silva et al. (2006).

Experimental

Crystal data

C₁₆H₁₂BrN₃O₂S
M_r = 390.26
Monoclinic, C 2/c
a = 32.149 (3) Å
b = 7.011 (1) Å
c = 16.589 (2) Å
= 117.86 (1)°
V = 3305.7 (7) Å³
Z = 8
Cu K radiation
= 4.68 mm^-1
T = 299 K
0.65 × 0.28 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.147, T_max = 0.626
3889 measured reflections
2942 independent reflections
2677 reflections with I > 2(I)
R_int = 0.035
3 standard reflections frequency: 120 min intensity decay: 1.5%

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.147
S = 1.05
2942 reflections
212 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.75 e Å^-3
_min = -1.00 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.89 (4)	2.18 (4)	2.959 (3)	146 (3)
N1-H1NN3	0.89 (4)	2.36 (3)	2.887 (4)	118 (3)
C10-H10O2ⁱⁱ	0.93	2.57	3.395 (4)	149
C12-H12O2ⁱⁱ	0.93	2.50	3.361 (5)	154
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z.

Data collection: CAD-4-PC (Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2087 ).

Acknowledgements

The authors thank Professor Dr Hartmut Fuess, FG Strukturforschung, Technische Universität Darmstadt, for diffractometer time.

References

Dueñas-Romero, A. M., Loiseau, P. M. & Saint-Pierre-Chazalet, M. (2006). Biochim. Biophys. Acta, 1768, 246-252.
Nonius (1996). CAD-4-PC. Nonius GmbH, Solingen, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Oliveira, K. N. de & Nunes, R. J. (2006). Synth. Commun. 36, 3401-3409.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Silva, L. L., de Oliveira, K. N. & Nunes, R. J. (2006). Arkivoc, xiii, 124-129.
Silva, L. E. da, Joussef, A. C., Pacheco, L. K., Duarte, A. M. C., Steindel, M. & Rebelo, R. A. (2007). Bioorg. Med. Chem. 15, 7553-7560.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.

organic compounds