1,2,3,4-Tetra­hydro­isoquinoline-2-sulfonamide

Radia Bouasla; Malika Berredjem; Nour-Eddine Aouf; Carole Barbey

doi:10.1107/S1600536807068158

. 2008 Jan 11;64(Pt 2):o432. doi: 10.1107/S1600536807068158

1,2,3,4-Tetrahydroisoquinoline-2-sulfonamide

Radia Bouasla ^a, Malika Berredjem ^a, Nour-Eddine Aouf ^a, Carole Barbey ^b,^*

PMCID: PMC2960235 PMID: 21201459

Abstract

The title compound, C₉H₁₂N₂O₂S, is a useful precursor of a variety of modified sulfonamide molecules. Due to the importance of these molecules in biological systems (antibacterials, antidepressants and many other applications), there is a growing interest in the discovery of new biologically active compounds. In the title compound, the molecules are linked by N—H⋯O intermolecular hydrogen bonds involving the sulfonamide function to form an infinite two-dimensional network parallel to the (001) plane.

Related literature

For related literature, see: Berredjem et al. (2000 ▶); Lee & Lee (2002 ▶); Martinez et al. (2000 ▶); Xiao & Timberlake (2000 ▶); Esteve & Bidal (2002 ▶); Soledade et al. (2006 ▶).

Experimental

Crystal data

C₉H₁₂N₂O₂S
M _r = 212.27
Monoclinic,
a = 5.275 (1) Å
b = 9.541 (1) Å
c = 10.229 (1) Å
β = 101.80 (5)°
V = 503.93 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 293 (2) K
0.10 × 0.10 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
8285 measured reflections
2210 independent reflections
2106 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.087
S = 1.13
2210 reflections
127 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ▶), 979 Friedel pairs
Flack parameter: −0.01 (6)

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97 and CrystalBuilder (DECOMET Laboratory, 2007 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068158/dn2304sup1.cif

e-64-0o432-sup1.cif^{(15KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068158/dn2304Isup2.hkl

e-64-0o432-Isup2.hkl^{(108.7KB, 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
N2—H21⋯O1ⁱ	0.91	2.03	2.928 (2)	173
N2—H22⋯O2ⁱⁱ	0.92	2.10	2.971 (2)	159

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

Acknowledgments

The authors thank Dr Pascal Retailleau from the Service de Cristallochimie of the Institut de Chimie des Substances Naturelles, CNRS, for help with data collection and processing. The authors acknowledge Professor Marc Lecouvey for his advice. This study was supported by the University Paris-Nord and the University of Annaba.

supplementary crystallographic information

Comment

The sulfamide unit is an ubiquitous structural entity in many naturally occurring compounds and medicinal agents (i.e. anticonvulsant, antihypertensive, hypoglycemic agents, histamine H2-receptor antagonist, herbicide, human cytomegalovirus inibitors···) (Soledade et al., 2006; Esteve & Bidal, 2002; Xiao & Timberlake, 2000; Martinez et al., 2000; Berredjem et al., 2000; Lee et al., 2002) We report herein the synthesis and the crystal structure determination of the title compound (Fig. 1).

The crystal structure consists of layers of hydrophobic regions that enclose the bicyclic moiety and polar regions where the sulfamide atoms are involved in hydrogen bond network. Namely, the sulfamide group is involved in four hydrogen bonds (2 with sulfamide O atoms, 2 with nitrogen atom) with four different symmetry-related molecules, building a two dimensional network parallel to the (0 0 1) plane (Table 1, Fig. 2).

Experimental

A solution of dimethyl malate (2,27 g, 14.1 mmol) in anhydrous CH₂Cl₂ (10 ml) was added to a stirring solution of chlorosulfonyl isocyanate (1.23 ml, 14.1 mmol) in CH₂Cl₂ (10 ml) at 0°C dropwise over period of 10 min. The resulting solution was transferred to a mixture of 1, 2, 3, 4 tetrahydroquinoleine (1,87 g, 14,1 mmol) in CH₂Cl₂ (20 ml) in the presence of triethylamine (1.1 equiv.). The solution was stirred at 0°C for less than 1.5 h. The reaction mixture was washed with HCl 0.1 N and water, and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Two compounds were obtained after purification by silica gel chromatography (Fig. 3). Slow evaporation at room temperature of a concentrated dichloromethane / methanol (9/1) solution of the most polar product (sulfamide I) afforded yellow crystals suitable for diffraction.