Diethyl 2,2′-[(5-dimethyl­amino-1-naphth­yl)sulfonyl­imino]diacetate

Yong Zhang; Yuan Qu; Ting Liu

doi:10.1107/S1600536809041476

. 2009 Oct 17;65(Pt 11):o2752. doi: 10.1107/S1600536809041476

Diethyl 2,2′-[(5-dimethylamino-1-naphthyl)sulfonylimino]diacetate

Yong Zhang ^a,^*, Yuan Qu ^a, Ting Liu ^a

PMCID: PMC2971309 PMID: 21578346

Abstract

In the title compound, C₂₀H₂₆N₂O₆S, the N atom of the dimethylamino group is displaced by 0.113 (2) Å from the plane of the naphthalene ring system. The two ethoxy groups adopt zigzag conformations. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link the molecules, forming a three-dimensional network. Both ethyl groups are disordered over two sites with the ratios of refined occupancies being 0.857 (16):0.143 (16) and 0.517 (14):0.483 (14).

Related literature

For applications of ligands containing the 5-(dimethylamino) naphthalene-1-sulfonyl (dansyl) group, see: Corradini et al. (1997 ▶); Christoforou et al. (2006 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C₂₀H₂₆N₂O₆S
M _r = 422.49
Monoclinic,
a = 13.1266 (9) Å
b = 8.4592 (5) Å
c = 19.3206 (12) Å
β = 93.530 (1)°
V = 2141.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.970, T _max = 0.981
16359 measured reflections
4201 independent reflections
3705 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.145
S = 1.05
4201 reflections
306 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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/S1600536809041476/lh2912sup1.cif

e-65-o2752-sup1.cif^{(24.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041476/lh2912Isup2.hkl

e-65-o2752-Isup2.hkl^{(205.9KB, 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
C4—H4⋯O1	0.93	2.36	3.006 (3)	126
C13—H13A⋯O2ⁱ	0.97	2.36	3.272 (3)	157

Open in a new tab

Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Dansyl (5-(dimethylamino)naphthalene-1-sulfonyl) derivatives are of considerable interest because of their good fluorescent properties. Many fluorescent ligands bearing dansyl group have been reported in recent years (e.g. Corradini et al., 1997; Christoforou et al., 2006; Zhang et al., 2009). We are interested in preparing fluorescent ligands that are expected to bind to hydrophobic sites in proteins or membranes. With this in mind, the title compound, (I), was prepared and we report herein the crystal stucture.

In the molecular structure (Fig. 1), the N atom of the dimethylamino group is displaced by 0.113 (2) Å from the plane of the naphthalene ring system. The two ethoxycarbonyl groups adopt coiled conformations with C14—O4—C15—C16 and C18—O6—C119—C20 torsion angles of 90.1 (10)° and 159.6 (9)°, respectively. All bond lengths and bond angles are as expected. In the crystal structure (Fig.2) weak intermolecular C—H···O hydrogen bonds lead to the formation of a three-dimension network.

Experimental

Diethyl iminodiacetate(0.38 g, 2 mmol) was added to a stirred solution of dansyl chloride(0.27 g, 1 mmol) in dry acetonitrile(40 ml). The reaction mixture was allowed to stir for 12 hr at 353 K. The progress of the reaction was monitored by TLC, untill the completion of reaction. The solvent was evaporated and the residue was purified by column chromatography (hexane-ethyl acetate,1:5 v/v) to afford the title compound as a yellow solid. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.