Benzyl­tributyl­ammonium 7-hydroxy­naphthalene-1-sulfonate

Sato, Y.; Uta, K.; Mizuguchi, J.

doi:10.1107/S1600536809001056

Volume 65
Part 2
Page o321
February 2009

Received 2 January 2009
Accepted 9 January 2009
Online 17 January 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R = 0.080
wR = 0.291
Data-to-parameter ratio = 15.5
Details

Benzyltributylammonium 7-hydroxynaphthalene-1-sulfonate

Yohei Sato,^a Kazuya Uta ^a and Jin Mizuguchi ^a ^*

^aDepartment of Applied Physics, Graduate School of Engineering, Yokohama National University, 79-5 Tokiwadai, Hodogaya-ku, 240-8501 Yokohama, Japan
Correspondence e-mail: mizu-j@ynu.ac.jp

The title compound, C₁₉H₃₄N⁺·C₁₀H₇O₄S^-, is a charge-control agent used for toners in electrophotography. The anions form one-dimensional chains by O-HO hydrogen bonds in a zigzag fashion along the c axis between the OH group of one anion and the sulfonate O atom of a neighboring anion. One of the n-butyl chains of the cation is disordered over two sites in a 0.77:0.23 ratio.

Related literature

For the function of charge-control agents, see: Nash et al. (2001) and for the structure of benzyltributylammonium 4-hydroxynaphthalene-1-sulfonate, benzyltributylammonium 6-hydroxynaphthalene-2-sulfonate, and benzyltributylammonium 4-hydroxynaphthalene-2-sulfonate see: Mizuguchi et al. (2007), Uta et al. (2009), and Uta & Mizuguchi (2009), respectively.

Experimental

Crystal data

C₁₉H₃₄N⁺·C₁₀H₇O₄S^-
M_r = 499.70
Monoclinic, P 2₁ /c
a = 19.8286 (6) Å
b = 8.8549 (2) Å
c = 16.7501 (4) Å
= 104.7570 (13)°
V = 2843.98 (13) Å³
Z = 4
Cu K radiation
= 1.27 mm^-1
T = 296.1 K
0.39 × 0.36 × 0.04 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.650, T_max = 0.951
24641 measured reflections
5082 independent reflections
2591 reflections with F² > 2(F²)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.080
wR(F²) = 0.291
S = 1.02
5082 reflections
328 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.71 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O4-H4OO1ⁱ	0.82	1.91	2.729 (3)	173
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SIR2004 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2845 ).

Acknowledgements

The authors express their sincere thanks to Mr O. Yamate at Orient Chemical Industries, Ltd for the preparation of the sample.

References

Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Mizuguchi, J., Sato, Y., Uta, K. & Sato, K. (2007). Acta Cryst. E63, o2509-o2510.
Nash, R. J., Grande, M. L. & Muller, R. N. (2001). Proceedings of the 7th International Conference on Advances in Non-Impact Printing Technology, pp. 358-364.
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2006). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Uta, K. & Mizuguchi, J. (2009). Acta Cryst. E65, o320.
Uta, K., Sato, Y. & Mizuguchi, J. (2009). Acta Cryst. E65, o319.

organic compounds