Benzyl­tributyl­ammonium 7-hydroxy­naphthalene-1-sulfonate

Yohei Sato; Kazuya Uta; Jin Mizuguchi

doi:10.1107/S1600536809001056

. 2009 Jan 17;65(Pt 2):o321. doi: 10.1107/S1600536809001056

Benzyltributylammonium 7-hydroxynaphthalene-1-sulfonate

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

PMCID: PMC2968364 PMID: 21581926

Abstract

The title compound, C₁₉H₃₄N⁺·C₁₀H₇O₄S⁻, is a charge-control agent used for toners in electrophotography. The anions form one-dimensional chains by O—H⋯O 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,
a = 19.8286 (6) Å
b = 8.8549 (2) Å
c = 16.7501 (4) Å
β = 104.7570 (13)°
V = 2843.98 (13) Å³
Z = 4
Cu Kα radiation
μ = 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 F ² > 2σ(F ²)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.080
wR(F ²) = 0.291
S = 1.02
5082 reflections
328 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.71 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001056/bt2845sup1.cif

e-65-0o321-sup1.cif^{(27.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001056/bt2845Isup2.hkl

e-65-0o321-Isup2.hkl^{(248.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O1ⁱ	0.82	1.91	2.729 (3)	173

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

The title compound is a charge-control-agent used for toners in electrophotography. The background of the present study has been set out in our previous paper (Uta et al., 2009). We have previously investigated the crystal structure of three isomers of compound (I) in connection with the mechanism of their high melting points [benzyltributylammonium 4-hydroxynaphthalene-1-sulfonate (Mizuguchi et al., 2007); benzyltributylammonium 6-hydroxynaphthalene-2-sulfonate (Uta et al., 2009); benzyltributylammonium 4-hydroxynaphthalene-4-sulfonate (Uta & Mizuguchi, 2009)]. The anions in the two former isomers are found to form chains of O—H···O intermolecular hydrogen bonds between the OH group of one anion and the sulfonate O atom of the neighboring one. The present hydrogen-bond network ensures a high thermal stability of these compounds as characterized by the melting points of 462 and 433K, respectively. On the other hand, the last isomer was characterized by a hydrogen-bonded dimer of the anions through O–H···O hydrogen bonding (melting point: 451 K). The present paper describes again one-dimensional chains of O—H···O intermoleclar hydrogen bonds.

Fig. 1 shows the ORTEPIII plot of the title compound. The ions have no crystallographically imposed symmetry. Fig. 2 shows a hydrogen-bonded chain along the c axis between the OH group of one anion and the sulfonic O atom of the neighboring one. The present linear chain is typically characterized by a zigzag form which is simlar to the one in benzyltributylammonium 4-hydroxynaphthalene-1-sulfonate (Mizuguchi et al., 2007) rather than the one in benzyltributylammonium 6-hydroxynaphthalene-2-sulfonate, Uta et al., 2009).

Experimental

The title compound was obtained from Orient Chemical Industries, Ltd, and was recrystallized from an acetone solution. After 48 h, a number of colorless crystals were obtained in the form of platelets. The title compound has a melting point of 439 K.