N-(2-Amino­ethyl)-5-(dimethyl­amino)naphthalene-1-sulfonamide

Shi-lei Zhang; Bi-lin Zhao; Zhen-hong Su; Xian-you Xia; Yong Zhang

doi:10.1107/S160053680901962X

. 2009 May 29;65(Pt 6):o1452. doi: 10.1107/S160053680901962X

N-(2-Aminoethyl)-5-(dimethylamino)naphthalene-1-sulfonamide

Shi-lei Zhang ^a,^*, Bi-lin Zhao ^a, Zhen-hong Su ^b, Xian-you Xia ^a, Yong Zhang ^a

PMCID: PMC2969652 PMID: 21583290

Abstract

In the title compound, C₁₄H₁₉N₃O₂S, the N atom of the dimethylamino group and the S atom are displaced by 0.078 (2) and 0.084 (2) Å, respectively, from the naphthalene ring plane. The 2-aminoethyl group has a coiled conformation with an N—C—C—NH₂ torsion angle of 53.6 (4)°. In the crystal structure, intermolecular N—H⋯N and weak C—H⋯O hydrogen bonds link molecules into chains along [001].

Related literature

For applications of ligands containing the 5-(dimethylamino)naphthalene-1-sulfonyl (dansyl) group, see: Corradini et al. (1996 ▶, 1997 ▶); Christoforou et al. (2006 ▶).

Experimental

Crystal data

C₁₄H₁₉N₃O₂S
M _r = 293.38
Orthorhombic,
a = 15.5221 (15) Å
b = 11.5423 (11) Å
c = 8.1360 (8) Å
V = 1457.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T _min = 0.956, T _max = 0.956
7478 measured reflections
3140 independent reflections
3012 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.107
S = 1.11
3140 reflections
192 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ▶), 1332 Friedel pairs
Flack parameter: −0.03 (8)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901962X/lh2821sup1.cif

e-65-o1452-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901962X/lh2821Isup2.hkl

e-65-o1452-Isup2.hkl^{(154.1KB, 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
C6—H6⋯O1	0.93	2.48	3.093 (3)	123
N3—H3A⋯N2	0.88 (5)	2.52 (6)	2.972 (4)	113 (4)
C11—H11⋯O1ⁱ	0.93	2.49	3.146 (3)	128
N2—H2D⋯N3ⁱⁱ	0.87 (3)	2.02 (4)	2.869 (4)	163 (3)

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

supplementary crystallographic information

Comment

The dansyl (5-(dimethylamino)naphthalene-1-sulfonyl) group has been widely used as a fluorophore in the design of fluorescent probes. Recently many fluorescent ligands bearing dansyl group have been reported (Corradini et al., 1996,1997; Christoforou et al., 2006). We are interested in preparing fluorescent ligands that are expected to bind to hydrophobic sites in proteins or membranes. With this mind, the title compound, (I), was prepared and we report the crystal stucture herein.

In the molecule (Fig. 1), atoms N1 and S1 are located approximately in the naphthalene ring plane with their deviations being 0.078 and 0.084 Å, respectively. The N2—C14—C15—N3 torsion angle of -53.6 (4)° indicates a coiled conformation for the aminoethyl group. In the crystal structure (Fig.2), intermolecular N—H···N and weak C-H···O hydrogen bonds link molecules into one-dimensional chains along [001].

Experimental

Compound (I) was synthesized according to a literature procedure (Corradini et al., 1996). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a dichloromethane solution of (I) at room temperature.