N-Benzyl-5-(dimethyl­amino)­naphthalene-1-sulfonamide

Pralav Bhatt; Thavendran Govender; Hendrik G Kruger; Glenn E M Maguire

doi:10.1107/S1600536811033083

. 2011 Aug 27;67(Pt 9):o2458–o2459. doi: 10.1107/S1600536811033083

N-Benzyl-5-(dimethylamino)naphthalene-1-sulfonamide

Pralav Bhatt ^a, Thavendran Govender ^b, Hendrik G Kruger ^a, Glenn E M Maguire ^a,^*

PMCID: PMC3200799 PMID: 22065719

Abstract

The structure of the title compound, C₁₉H₂₀N₂O₂S, displays intermolecular N—H⋯O hydrogen bonding, which generates inversion dimers. There is no π–π stacking in the crystal structure. The dihedral angle between the phenyl ring and naphthalene ring system is 59.16 (11)°.

Related literature

For the use of dansyl fluorescent analogs as insecticides and synergists, see: Himel et al. (1971 ▶). Dansyl probes have also been covalently incorporated into a variety of polymeric networks, see: Shea et al. (1989 ▶). Dansyl chromophoric compounds have been investigated for intramolecular energy transfer in aromatic ring systems, see: Schael et al. (1998 ▶) and for host–guest interations shown by fluoresence studies of dansyl-labelled calix[6]arene, see: Schonefeld et al. (2006 ▶). For related structures, see: Illos et al. (2005 ▶); Hongmei et al. (2009 ▶); Hong-Wei et al. (2009 ▶); Chui et al. (2010 ▶).

Experimental

Crystal data

C₁₉H₂₀N₂O₂S
M _r = 340.43
Monoclinic,
a = 16.6635 (5) Å
b = 9.5722 (2) Å
c = 22.8942 (7) Å
β = 108.779 (1)°
V = 3457.38 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.30 × 0.24 × 0.22 mm

Data collection

Nonius KappaCCD diffractometer
4275 measured reflections
4275 independent reflections
3747 reflections with I > 2σ(I)

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.096
S = 1.03
4275 reflections
223 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033083/hg5080sup1.cif

e-67-o2458-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033083/hg5080Isup2.hkl

e-67-o2458-Isup2.hkl^{(209.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811033083/hg5080Isup3.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⋯O2ⁱ	0.86 (2)	2.12 (2)	2.9351 (14)	158 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors wish to thank Dr Hong Su from the University of the Cape Town for her assistance with the data collection and refinement.

supplementary crystallographic information

Comment

Dansyl fluorescent analogs have been reported as insecticides and synergists (Himel et al.,1971). Dansyl probes have also been covalently incorporated into a variety of polymeric networks (Shea et al.,1989). Dansyl chromophoric compounds were investigated for intramolecular energy transfer in aromatic ring systems (Schael et al.,1998). Dansyl labelled calix[6]arene are reported to show host–guest interations using fluoresence studies (Schonefeld et al., 2006).

The title compound is a novel benzylated dansyl derivative (Fig. 1.).

There are a number of examples in literature where amino-sulfonamides dansyl structures have shown intermolecular hydrogen bonding. These arrangments can be described in two broad categories. First, where hydrogen bonds occur between the sulfonyl oxygen and the nitrogen of two adjacent molecules in a alternating chain arrangement (Hongmei et al., 2009, Chui et al.,2010). Second, where they interact with an adjacent molecule in a head to tail manner, (Illos et al., 2005, Hong-Wei et al., 2009). Our system falls into the latter category. Our structure thus displays N1—H1···O2, 2.9351 (14) Å intermolecular hydrogen bonding, generating inversion dimers (Fig. 2). There is no π–π stacking in the crystal.

Experimental

To a dry THF 5 ml benzyl amine (107 mg, 1 mM) was added triethyl amine (303 mg, 3 mM). Dansyl chloride (269 mg, 1 mM) was then added and the resulting solution was stirred until the reaction was completed (TLC R_f = 0.27 in 60% ethyl acetate/hexane). The reaction contents were filtered. The filtrate was evaporated under reduced pressure yielding a yellow oil. To this residue was added 20 ml of dichloromethane and then the organic layer was washed with water and then separated. After drying over anhydrous magnesium sulfate the solvent was evaporated once again under reduced pressure to yield a yellow crystalline solid (240 mg, 71%). M.p. = 408 K.

Crystals suitable for X-ray analysis were grown in ethyl acetate/hexane at room temperature.