Phenyl naphthalene-2-sulfonate

Jasmine P Vennila; Helen P Kavitha; D John Thiruvadigal; V Manivannan

doi:10.1107/S1600536808035824

. 2008 Nov 8;64(Pt 12):o2304. doi: 10.1107/S1600536808035824

Phenyl naphthalene-2-sulfonate

Jasmine P Vennila ^a, Helen P Kavitha ^b, D John Thiruvadigal ^c, V Manivannan ^d,^*

PMCID: PMC2959821 PMID: 21581281

Abstract

In the crystal structure of the title compound, C₁₆H₁₂O₃S, the dihedral angle between the naphthalene ring system and the phenyl ring is 65.21 (3)°. The molecules are linked by intermolecular C—H⋯O hydrogen bonds, forming a chain along the a axis. The chains are connected through weak C—H⋯π interactions.

Related literature

For general background, see: Spungin et al. (1984 ▶); Yachi et al. (1989 ▶). For related structures, see: Manivannan et al. (2005 ▶); Ramachandran et al. (2007 ▶).

Experimental

Crystal data

C₁₆H₁₂O₃S
M _r = 284.32
Orthorhombic,
a = 6.1525 (2) Å
b = 12.7466 (7) Å
c = 17.3414 (10) Å
V = 1359.97 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 295 (2) K
0.25 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.942, T _max = 0.962
11868 measured reflections
5093 independent reflections
3412 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.106
S = 1.01
5093 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.31 e Å⁻³
Absolute structure: Flack (1983 ▶), 1993 Friedel pairs
Flack parameter: −0.03 (7)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035824/is2352sup1.cif

e-64-o2304-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035824/is2352Isup2.hkl

e-64-o2304-Isup2.hkl^{(244.4KB, 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
C2—H2⋯O2ⁱ	0.93	2.51	3.424 (2)	169
C5—H5⋯Cg2ⁱⁱ	0.93	2.96	3.486 (2)	117
C6—H6⋯Cg3ⁱⁱ	0.93	2.94	3.535 (2)	123
C12—H12⋯Cg1ⁱⁱⁱ	0.93	2.94	3.788 (3)	152

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 ring, Cg2 is the centroid of the C7–C9/C14–C16 ring and Cg3 is the centroid of the C9–C14 ring.

Acknowledgments

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Madras, for the data collection.

supplementary crystallographic information

Comment

Several compounds containing the para -toluene sulfonate moiety are used in the fields of biology and industry. The merging of lipids can be monitored using a derivative of para-toluene sulfonate (Yachi et al., 1989). This method has been used in studying the membrane fusion during the acrosome reaction (Spungin et al., 1984).

The geometric parameters in the title compound (I) agree well with the reported values of similar structures (Manivannan et al., 2005; Ramachandran et al., 2007). The phenyl ring makes a dihedral angle of 65.21 (3)° with the naphthalene ring system. The torsion angles of O2—S1—C7—C8 and O3—S1—C7—C16 [2.04 (15)° and 46.94 (15)°, respectively] indicate the syn conformation of the sulfonyl moiety. The crystal structure is stabilized through weak intermolecular C—H···O and C—H···π interactions (Fig. 2 and Table 1). Cg1, Cg2 and Cg3 are the centroids of the C1–C6 ring, the C7–C9/C14–C16 ring and the C9–C14 ring, respectively.

Experimental

2-Naphthalene sulfonyl chloride (2.5 mmol) dissolved in acetone (4 ml) was added dropwise to phenol (2.5 mmol) in aqueous NaOH solution (4 ml, 5%) with constant shaking. The precipitated compound (2 mmol, yield 77%) recrystallized from ethanol yielded colourless crystals.