4-({4-[Bis(2-cyano­eth­yl)amino]­phen­yl}diazen­yl)benzene­sulfonamide

Gervasio, G.; Marabello, D.; Bertolotti, F.

doi:10.1107/S1600536810053158

Volume 67
Part 1
Page o231
January 2011

Received 9 December 2010
Accepted 17 December 2010
Online 24 December 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R = 0.050
wR = 0.055
Data-to-parameter ratio = 16.8
Details

4-({4-[Bis(2-cyanoethyl)amino]phenyl}diazenyl)benzenesulfonamide

Giuliana Gervasio,^a ^* Domenica Marabello ^a and Federica Bertolotti ^a

^aDipartimento di Chimica I,F.M. e Centro CrisDi, University of Turin, Via P. Giuria 7, 10125 Torino, Italy
Correspondence e-mail: giuliana.gervasio@unito.it

In the title compound, C₁₈H₁₆N₆O₂S, which belongs to the family of azo dyes, the dihedral angle between the benzene rings is 26.16 (7)°. In the crystal, molecules are joined by N-HN and C-HN hydrogen bonds into double chains parallel to the a axis.

Related literature

For the synthesis and properties of azo dyes, see: Wenker (1935); Ledoux et al. (2000); Viscardi et al. (2002). For a related structure, see: Sasaki et al. (2004).

Experimental

Crystal data

C₁₈H₁₈N₆O₂S
M_r = 382.45
Triclinic, $[P \overline 1]$
a = 7.8093 (16) Å
b = 11.035 (2) Å
c = 11.776 (3) Å
= 94.268 (4)°
= 106.544 (4)°
= 104.568 (5)°
V = 929.8 (3) Å³
Z = 2
Mo K radiation
= 0.20 mm^-1
T = 295 K
0.30 × 0.23 × 0.03 mm

Data collection

Siemens-Bruker APEX diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995) T_min = 0.93, T_max = 1.00
9271 measured reflections
4100 independent reflections
1577 reflections with I > 2(I)
R_int = 0.040
15 standard reflections every 60 min intensity decay: none

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.055
S = 0.86
4100 reflections
244 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.40 e Å^-3
_min = -0.48 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C15-H15AN23ⁱ	0.93	2.52	3.427 (4)	166
N10-H10BN27ⁱⁱ	0.91 (2)	2.19 (2)	3.084 (2)	165
N10-H10AN12ⁱⁱⁱ	0.94 (2)	2.19 (2)	3.124 (2)	176
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x, -y, -z+1; (iii) x-1, y, z.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2541 ).

Acknowledgements

We thank Dr C. Barolo for supplying crystals of the title compound.

References

Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Bruker (2007). SMART and SAINT. Bruker AXS Inc, Madison,Wisconsin, USA.
Ledoux, I., Zyss, J., Barni, E., Barolo, C., Diulgheroff, N. & Quagliotto, P. (2000). Synth. Met. 115, 213-217.
Sasaki, C., Kitoh, S., Hayashi, H. & Kunimoto, K.-K. (2004). Anal. Sci. X-ray Struct. Anal Online, 20, x117-x118.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Viscardi, G., Quagliotto, P., Barolo, C., Diulgheroff, N., Caputo, G. & Barni, E. (2002). Dyes Pigments, 54, 131-140.
Wenker, H. (1935). Ind. Eng. Chem. Anal. 27, 40-41.

organic compounds