N-(2-{[5-Bromo-2-(piperidin-1-yl)pyrimidin-4-yl]sulfan­yl}-4-meth­oxy­phen­yl)-4-methyl­benzene­sulfonamide

Mohan Kumar; L Mallesha; M A Sridhar; Kamini Kapoor; Vivek K Gupta; Rajni Kant

doi:10.1107/S1600536812037257

. 2012 Sep 1;68(Pt 10):o2831. doi: 10.1107/S1600536812037257

N-(2-{[5-Bromo-2-(piperidin-1-yl)pyrimidin-4-yl]sulfanyl}-4-methoxyphenyl)-4-methylbenzenesulfonamide

Mohan Kumar ^a, L Mallesha ^b, M A Sridhar ^a,^*, Kamini Kapoor ^c, Vivek K Gupta ^c, Rajni Kant ^c

PMCID: PMC3470193 PMID: 23125637

Abstract

In the title compound, C₂₃H₂₅BrN₄O₃S₂, the benzene rings bridged by the sulfonamide group are tilted relative to each other by 69.7 (1)° and the dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 70.4 (1)°. The molecular conformation is stabilized by a weak intramolecular π–π stacking interaction between the pyrimidine and the 4-methyl benzene rings [centroid–centroid distance = 3.633 (2) Å]. The piperidine ring adopts a chair conformation. In the crystal, molecules are linked into inversion dimers by pairs of N—H⋯O hydrogen bonds.

Related literature

For a related structure and background to sulfonamides, see: Kant et al. (2012 ▶).

Experimental

Crystal data

C₂₃H₂₅BrN₄O₃S₂
M _r = 549.50
Triclinic,
a = 9.8318 (3) Å
b = 10.3822 (3) Å
c = 13.4393 (4) Å
α = 96.654 (3)°
β = 103.085 (3)°
γ = 107.714 (3)°
V = 1247.36 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.85 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur CCD, Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.764, T _max = 1.000
41580 measured reflections
4385 independent reflections
3645 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.093
S = 1.03
4385 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037257/hb6947sup1.cif

e-68-o2831-sup1.cif^{(30.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037257/hb6947Isup2.hkl

e-68-o2831-Isup2.hkl^{(210.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812037257/hb6947Isup3.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
N8—H8⋯O2ⁱ	0.86	2.22	2.955 (4)	143

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Symmetry code: (i) Inline graphic .

Acknowledgments

MK acknowledges the help of Bahubali College of Engineering, Shravanabelagola for his research work and RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

supplementary crystallographic information

Comment

As part of our ongoing studies of sulfonamides (Kant et al., 2012), we now report the structure of the title compound, (I), (Fig. 1).

The piperidine ring is exhibiting a chair conformation. The two benzene rings (C1—C6/C9—C14) are tilted relative to each other by 69.7 (1)° and the dihedral angle between the sulfur bridged pyrimidine and benzene rings is 70.4 (1)°. The molecular conformation is stabilized by a weak intramolecular stacking interaction between the pyrimidine and the 4 -methyl benzene rings [centroid–centroid distance = 3.633 (2) Å, interplanar spacing = 3.494 Å, and centroid shift = 1.00 Å]. In the crystal, molecules are linked into inversion dimers by pairs of N8—H8···O2 hydrogen bonds (Fig.2).

Experimental

The reaction of N-[2-(5-bromo-2-piperidin-1-yl-pyrimidin-4-ylsulfanyl)-4-methoxy -phenyl]-4-methyl-benzenesulfonamide (5.01 g, 0.01 mol) and piperidine (0.86 g, 0.01 mol) were carried out in the presence of triethylamine and the reaction mixture was allowed to stir at room temperature for 6–7 h in dry dichloromethane. The progress of the reaction was monitored by TLC. Upon completion, the solvent was removed under reduced pressure and residue was extracted with ethyl acetate. The compound was purified by successive recrystallization from methanol (yield 83%, m. p. 483–485 K) to yield light brown blocks of (I).