N-(1-Naphth­yl)benzene­sulfonamide

Sifang Zhang; Yuewen Zhang; Chuntao Wang; Ruitao Zhu

doi:10.1107/S1600536811039201

. 2011 Oct 5;67(Pt 11):o2831. doi: 10.1107/S1600536811039201

N-(1-Naphthyl)benzenesulfonamide

Sifang Zhang ^a, Yuewen Zhang ^a, Chuntao Wang ^a, Ruitao Zhu ^a,^*

PMCID: PMC3247570 PMID: 22219875

Abstract

In the title compound, C₁₆H₁₃NO₂S, the C—SO₂—NH—C torsion angle is −70.1 (2)°. The dihedral angle between the planes of the naphthyl ring system and the phenyl ring is 34.67 (4)°. In the crystal, molecules are linked by intermolecular N—H⋯O hydrogen bonds into chains along [100]. There are also π–π interactions between adjacent naphthyl groups [interplanar spacing = 3.541 (3) Å] for molecules stacked along [100].

Related literature

For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001 ▶). For related structures, see: Shakuntala et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₃NO₂S
M _r = 283.33
Orthorhombic,
a = 4.9232 (5) Å
b = 15.4162 (15) Å
c = 18.2102 (17) Å
V = 1382.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 K
0.43 × 0.33 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.906, T _max = 0.929
6917 measured reflections
2438 independent reflections
2178 reflections with I > σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.084
S = 1.09
2438 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ▶), 983 Friedel pairs
Flack parameter: 0.06 (9)

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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039201/pk2348sup1.cif

e-67-o2831-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039201/pk2348Isup2.hkl

e-67-o2831-Isup2.hkl^{(119.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039201/pk2348Isup3.cml

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
N1—H1⋯O1ⁱ	0.90	2.05	2.911 (3)	159

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Symmetry code: (i) Inline graphic .

Acknowledgments

We would like to thank the Natural Science Foundation of Shanxi Province for financial support (2011011007–2).

supplementary crystallographic information

Comment

Sulfonamide moieties are constituents of many biologically important compounds. The hydrogen bonding preferences of sulfonamides has been investigated (Adsmond & Grant, 2001). In this paper, we present the crystal structure of the title compound.

The molecular structure of is shown in Fig. 1. The bond lengths (Allen et al., 1987) and angles are normal. The molecule is twisted at the S atom with C—SO₂—NH—C torsion angle of -70.14 (2) °. The dihedral between the planes of the naphthyl and benzene groups is 34.67 (4) °. In the crystal, molecules are linked by intermolecular N—H···O hydrogen bonds into chains along [100]. There are also π-π interactions between adjacent naphthyl groups (interplanar spacing 3.541 (3) Å) for molecules stacked along [100].

Experimental

To a 100 ml round flask fitted with a condenser was added 1-naphthylamine (1.43 g, 10 mmol), dichloromethane (15 ml) and triethylamine(0.5 ml) with magnetic stirring. Benzenesulfonyl chloride (1.76 g, 10 mmol) was added gradually. The reaction mixture was stirred at room temperature for 1 h and then refluxed for 2 h. The product precipitated as a white powder, which was washed three times with water and dichloromethane. Recrystallization from ethyl alcohol produced the crystals of the title compound.