6-Chloro-N-(pyridin-4-ylmeth­yl)pyridine-3-sulfonamide

Parameshwar Adimoole Suchetan; Revanasiddappa Nadigar Mohan; Vijithkumar; Bandrehalli Siddagangaiah Palakshamurthy; Swamy Sreenivasa

doi:10.1107/S1600536813030523

. 2013 Nov 13;69(Pt 12):o1765. doi: 10.1107/S1600536813030523

6-Chloro-N-(pyridin-4-ylmethyl)pyridine-3-sulfonamide

Parameshwar Adimoole Suchetan ^a, Revanasiddappa Nadigar Mohan ^a, Vijithkumar ^b, Bandrehalli Siddagangaiah Palakshamurthy ^c, Swamy Sreenivasa ^a,^*

PMCID: PMC3885039 PMID: 24454215

Abstract

In the title sulfonamide derivative, C₁₁H₁₀ClN₃O₂S, the dihedral angle between the pyridine rings is 46.85 (12)°. The N atom of the chloropyridine ring is anti to the N—H bond. In the crystal, molecules are linked through N—H⋯N hydrogen bonds into zigzag chains parallel to [001] with a C(7) graph-set motif.

Related literature

For graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995 ▶). For the antimicrobial activity of related compounds, see: Desai et al. (2013 ▶); Mohan et al. (2013 ▶). For the proliferation activity of these compounds, see: Renu et al. (2006 ▶), and for their tuberculostaic acitivity, see: Gobis et al. (2013 ▶). graphic file with name e-69-o1765-scheme1.jpg

Experimental

Crystal data

C₁₁H₁₀ClN₃O₂S
M _r = 283.73
Monoclinic,
a = 5.4140 (6) Å
b = 18.172 (2) Å
c = 12.9392 (15) Å
β = 92.388 (6)°
V = 1271.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 293 K
0.35 × 0.29 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.852, T _max = 0.899
20929 measured reflections
2961 independent reflections
2185 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.137
S = 0.82
2961 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813030523/wm2782sup1.cif

e-69-o1765-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030523/wm2782Isup2.hkl

e-69-o1765-Isup2.hkl^{(142.4KB, hkl)}

Click here for additional data file.^{(4.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813030523/wm2782Isup3.cml

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—HN2⋯N3ⁱ	0.78 (3)	2.10 (3)	2.870 (3)	174.53

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Prof T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for his help and valuable suggestions.

supplementary crystallographic information

1. Comment

Pyridine ring containing sulfonamide moieties show antimicrobial activity (Desai et al., 2013; Mohan et al., 2013), proliferation activity (Renu et al., 2006) and tuberculostaic acitivity (Gobis et al., 2013). Keeping this in mind, the title compound, C₁₁H₁₀ClN₃O₂S, (I), was synthesized and its crystal structure determined.

In the structure of compound (I) the dihedral angle between the two pyridine rings is 46.85(12°. The N-atom of the chloropyridine ring in the compound is anti to the N—H bond (Fig 1). In the crystal structure, the molecules are linked through N2—HN2···N3 hydrogen bonds (Table 1, Fig. 2) into zigzag chains with graph-set notation C(7) (Bernstein et al. 1995) running parallel to [001] .

2. Experimental

Pyridin-4-ylmethanamine (7.4 mmol) was taken in dry dichloromethane (10 ml) and cooled to 273 K. To this solution 6-chloropyridine-3-sulfonyl chloride (7.4 mmol) in dichloromethane and triethylamine (1.48 mmol) was added slowly and the solution was heated to 323 K for 4 h. The reaction was monitored by TLC. The reaction mixture was cooled and washed with 10% sodium bicarbonate solution. The organic layer was separated, dried and concentrated to obtain the crude compound. It was purified by column chromatography using petroleum ether: ethyl acetate (7:3) as eluent.

Yellow prisms of the title compound suitable for diffraction studies were obtained from evapouration of the solution of the compound in a mixture of petroleum ether: ethyl acetate (7:3).