N-Benzyl­pyridine-2-sulfonamide

Xiao-Ping Chen; Shou-Fa Han

doi:10.1107/S1600536809018054

. 2009 May 29;65(Pt 6):o1414. doi: 10.1107/S1600536809018054

N-Benzylpyridine-2-sulfonamide

Xiao-Ping Chen ^a, Shou-Fa Han ^a,^*

PMCID: PMC2969775 PMID: 21583257

Abstract

The title compound, C₁₂H₁₂N₂O₂S, was obtained by the reaction of 2-mercaptopyridine and benzylamine. The dihedral angle between the benzene and pyridine rings is 75.75 (9)°. In the crystal, molecules are linked into chains along the c axis by N—H⋯O and N—H⋯N hydrogen bonds; the chains are cross-linked into a two-dimensional network parallel to the bc plane via C—H⋯O hydrogen bonds.

Related literature

For the synthesis, see: Wright et al. (2006 ▶). For applications of sulfonamides, see: Connor (1998 ▶). For the structure of N-benzylquinoline-8-sulfonamide, see: Andrighetti-Fröhner et al. (2006 ▶).

Experimental

Crystal data

C₁₂H₁₂N₂O₂S
M _r = 248.30
Monoclinic,
a = 11.099 (2) Å
b = 10.709 (2) Å
c = 9.513 (2) Å
β = 91.893 (4)°
V = 1130.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 173 K
0.50 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.823, T _max = 1.00 (expected range = 0.783–0.951)
5922 measured reflections
2195 independent reflections
2078 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.101
S = 1.00
2195 reflections
157 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018054/ci2800sup1.cif

e-65-o1414-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018054/ci2800Isup2.hkl

e-65-o1414-Isup2.hkl^{(108KB, 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
N1—H1⋯N2ⁱ	0.82 (2)	2.49 (2)	3.264 (2)	157 (2)
N1—H1⋯O1ⁱ	0.82 (2)	2.50 (2)	3.111 (2)	132 (2)
C4—H4⋯O1ⁱⁱ	0.95	2.52	3.406 (2)	154
C5—H5⋯O2ⁱⁱⁱ	0.95	2.51	3.121 (2)	122

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

Acknowledgments

The authors thank the National Science Foundation of China (grant No. 20802060) for supporting this work.

supplementary crystallographic information

Comment

Sulfonamides are an important category of pharmaceutical compounds with a broad spectrum of biological activities, as good antibacterials, diuretics, anticonvulsants, and HIV protease inhibitors (Connor, 1998).

The molecular structure of the title compound is shown in Fig. 1. Bond lengths and angles are comparable to those observed for N-benzylquinoline-8-sulfonamide (Andrighetti-Fröhner et al., 2006). The C1—S1—N1—C6 torsion angle is -71.85 (15)°. The dihedral angle between the benzene and pyridine rings is 75.75 (9)°.

Hydrogen bonding plays a significant role in stabilizing the crystal structure; see Table 1 for geometric parameters and symmetry operations. The molecules are linked into a chain along the c axis by N—H···O and N—H···N hydrogen bonds. The chains are cross-linked via C—H···O hydrogen bonds to form a two-dimensional network parallel to the bc plane.

Experimental

The title compound was synthesized using a similar synthetic method for the preparation of heteroaryl sulfonamides (Wright et al., 2006). 2-Mercaptopyridine (0.56 g, 5 mmol) was stirred in a mixture of 25 mL of dichloromethane and 25 mL of 1 M HCl in a 125 ml flask for 8 min at 263 to 268 K. Cold sodium hypochlorite (6% solution, 0.68 M, 26 ml, 18 mmol, 3.3 equiv) was then added dropwise with very rapid stirring, maintaining the internal temperature at 263 to 268 K. The mixture was stirred for 30 min at 263 to 268 K after the addition was completed, the mixture was transferred to a separatory funnel (pre-cooled with ice water) and the dichloromethane layer was rapidly separated and collected in a clean 125 ml flask cooled in a ice-salt bath. Benzylamine (1.1 ml, 10 mmol) was added with stirring, when the dichloromethane layer became a white suspension, the flask was removed to an ice-water bath and the suspension was stirred for 30 min at 273 K. The suspension was then washed with 1 M HCl, then with water and brine. Drying (MgSO₄) and concentration afforded the title compound as a white solid with 81% yield. Single crystals of the title compound were grown in a petroleum ether-ethyl acetate solution (3:1 v/v) by slow evaporation.