5-(1H-Imidazol-1-ylsulfon­yl)-N,N-dimethyl­naphthalen-1-amine

Lei Teng; Yong Zhang; Shi-lei Zhang; Yuan Qu; Xian-you Xia

doi:10.1107/S160053680804066X

. 2008 Dec 10;65(Pt 1):o55. doi: 10.1107/S160053680804066X

5-(1H-Imidazol-1-ylsulfonyl)-N,N-dimethylnaphthalen-1-amine

Lei Teng ^a, Yong Zhang ^a,^*, Shi-lei Zhang ^a, Yuan Qu ^a, Xian-you Xia ^a

PMCID: PMC2967969 PMID: 21581696

Abstract

In the title molecule, C₁₅H₁₅N₃O₂S, the dihedral angle between the naphthalene ring system and the imidazole ring is 86.1 (2)°. In the crystal structure, weak intermolecular C—H⋯O and C—H⋯N hydrogen bonds, as well as weak C—H⋯π interactions, connect molecules, forming a two-dimensional network.

Related literature

For background information, see: Corradini et al. (1997 ▶); Kavallieratos et al. (2005 ▶); Koike et al. (1996 ▶). For the synthesis, see: Hilderbrand et al. (2004 ▶).

Experimental

Crystal data

C₁₅H₁₅N₃O₂S
M _r = 301.36
Orthorhombic,
a = 16.3707 (16) Å
b = 7.7928 (7) Å
c = 22.088 (2) Å
V = 2817.8 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 150 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.944, T _max = 0.977
9800 measured reflections
2577 independent reflections
2196 reflections with I > 2σ(I)
R _int = 0.058

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.110
S = 1.07
2577 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.31 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, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680804066X/lh2737sup1.cif

e-65-00o55-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680804066X/lh2737Isup2.hkl

e-65-00o55-Isup2.hkl^{(126.7KB, 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⋯O2	0.95	2.42	3.057 (2)	125
C15—H15⋯N3ⁱ	0.95	2.45	3.395 (3)	173
C14—H14⋯O2ⁱⁱ	0.95	2.45	3.358 (3)	161
C13—H13⋯N1ⁱⁱⁱ	0.95	2.57	3.506 (2)	169
C10—H10⋯Cg^iv	0.95	2.82	3.302 (2)	113

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg is the centroid of the C3–C7/C12 ring.

supplementary crystallographic information

Comment

Dansyl chloride is widely used as a fluorescent label in immunofluorescence methods and in yielding fluorescent N-terminal amino acids and peptide derivatives. Some dansyl chloride derivatives are also used as fluorescent probes, which can detect trace metal ions such as Pb²⁺, Cu²⁺, Zn²⁺ (Koike et al., 1996; Corradini et al., 1997; Kavallieratos et al., 2005). We are interested in preparing fluorescent drug or ligand analogs 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 molecular structure (Fig. 1), the dihedral angle between the naphthalene ring and the imidazole ring is 86.1 (2)°. All bond lengths and bond angles are as expected. In the crystal structure (Fig.2), the molecules are linked by C–H···O and C—H···N hydrogen bonds (Table 1) and C—H···π interactions into a two-dimension network.

Experimental

Compound (I) was synthesized according to a literature procedure (Hilderbrand et al., 2004). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution of (I) at room temperature.