3-Amino­phenyl naphthalene-1-sulfonate

Jasmine P Vennila; Helen P Kavitha; D John Thiruvadigal; B R Venkatraman; V Manivannan

doi:10.1107/S1600536808041032

. 2008 Dec 10;65(Pt 1):o72. doi: 10.1107/S1600536808041032

3-Aminophenyl naphthalene-1-sulfonate

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

PMCID: PMC2967982 PMID: 21581711

Abstract

In the title compound, C₁₆H₁₃NO₃S, the plane of the naphthalene ring system forms a dihedral angle of 64.66 (10)° with the benzene ring. The molecular structure is stabilized by weak intramolecular C—H⋯O interactions and the crystal packing is stabilized by weak intermolecular N—H⋯O and C—H⋯O interactions and by π–π stacking interactions of the inversion-related naphthalene units [centroid–centroid distance of 3.7373 (14) Å].

Related literature

For the structures of closely related compounds, see: Manivannan et al. (2005a ▶,b ▶); Ramachandran et al.(2007 ▶); Vennila et al. (2008 ▶). For applications, see: Spungin et al. (1984 ▶); Yachi et al. (1989 ▶).

Experimental

Crystal data

C₁₆H₁₃NO₃S
M _r = 299.33
Monoclinic,
a = 8.4558 (2) Å
b = 8.6712 (3) Å
c = 19.5915 (6) Å
β = 100.321 (2)°
V = 1413.24 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 295 (2) K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.932, T _max = 0.954
19808 measured reflections
4981 independent reflections
3126 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.174
S = 1.05
4981 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: 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 I, global. DOI: 10.1107/S1600536808041032/gk2179sup1.cif

e-65-00o72-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041032/gk2179Isup2.hkl

e-65-00o72-Isup2.hkl^{(239KB, 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⋯O2	0.93	2.41	2.829 (3)	107
C9—H9⋯O3	0.93	2.56	3.127 (3)	120
N1—H1B⋯O3ⁱ	0.86	2.43	3.246 (3)	158
C7—H7⋯O2ⁱⁱ	0.93	2.56	3.422 (3)	154

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Symmetry codes: (i) Inline graphic ; (ii) .

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 plane of the benzene ring forms a dihedral angle of 64.66 (10) ° with the naphthalene ring system. The torsion angles O2—S1—C1—C2 and O3—S1—C1—C10 [5.58 (17) ° and 52.09 (16) °, respectively] indicate the syn conformation of sulfonyl moiety. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak intermolecular C—H···O interactions, N—H···O interactions and π-π stacking interactions of the naphthalene fragments related by inversion center

Experimental

1-Napthalene sulfonyl chloride (5 mmol) dissolved in acetone (4 ml) was added dropwise to 3-amino phenol (5 mmol) in aqueous NaOH (4 ml, 5%) with constant shaking. The precipitated compound (3 mmol, yield 60%) was recrystlized from ethanol to get diffraction quality brown colored crystals.