N-(2-{[5-Bromo-2-(piperidin-1-yl)pyrimidin-4-yl]sulfan­yl}-4-meth­oxy­phen­yl)-2,4,6-trimethyl­benzene­sulfonamide

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

doi:10.1107/S1600536812036185

. 2012 Aug 25;68(Pt 9):o2767. doi: 10.1107/S1600536812036185

N-(2-{[5-Bromo-2-(piperidin-1-yl)pyrimidin-4-yl]sulfanyl}-4-methoxyphenyl)-2,4,6-trimethylbenzenesulfonamide

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

PMCID: PMC3435802 PMID: 22969648

Abstract

In the title compound, C₂₅H₂₉BrN₄O₃S₂, the benzene rings bridged by the sulfonamide group are tilted relative to each other by 63.9 (1)° and the dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 64.9 (1)°. The molecular conformation is stabilized by a weak intramolecular π–π stacking interaction between the pyrimidine and the 2,4,6-trimethylbenzene rings [centroid–centroid distance = 3.766 (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 and these dimers are further linked by C—H⋯O hydrogen bonds into chains propagating along [010].

Related literature

For the crystal structures of related sulfonamides, see: Rodrigues et al. (2011 ▶); Akkurt et al. (2011 ▶); Kant et al. (2012 ▶).

Experimental

Crystal data

C₂₅H₂₉BrN₄O₃S₂
M _r = 577.55
Monoclinic,
a = 9.3334 (5) Å
b = 10.3635 (4) Å
c = 27.8258 (11) Å
β = 92.924 (4)°
V = 2688.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.72 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.649, T _max = 1.000
21429 measured reflections
5266 independent reflections
3580 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.123
S = 1.06
5266 reflections
320 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.43 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/S1600536812036185/hb6940sup1.cif

e-68-o2767-sup1.cif^{(32.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036185/hb6940Isup2.hkl

e-68-o2767-Isup2.hkl^{(252.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812036185/hb6940Isup3.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
N1—H1⋯O2ⁱ	0.86	2.03	2.880 (5)	172
C8—H8A⋯O2ⁱⁱ	0.96	2.48	3.242 (5)	136
C11—H11⋯O1ⁱⁱⁱ	0.93	2.50	3.387 (6)	159

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

Acknowledgments

MK acknowledges the help of Bahubali College of Engineering for his research work. 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

Bond lengths and angles in the title compound (Fig. 1) are comparable with those in similar crystal structures (Rodrigues et al., 2011; Akkurt et al., 2011; Kant et al., 2012). The piperidine ring is exhibiting a chair conformation. The two benzene rings (C1—C6/C9—C14) are tilted relative to each other by 63.9 (1)° and the dihedral angle between the sulfur bridged pyrimidine and benzene rings is 64.9 (1)°. The molecular conformation is stabilized by a weak intramolecular stacking interaction between the pyrimidine and the 2,4,6 -trimethyl benzene rings [centroid–centroid distance = 3.766 (2) Å, interplanar spacing = 3.507 Å, and centroid shift = 1.37 Å]. In the crystal, molecules are linked into dimers by pairs of N1—H1···O2 hydrogen bonds and these dimers are further linked by C—H···O hydrogen bonds into chains along [010](Fig.2).

Experimental

The reaction of N-[2-(5-bromo-2-chloro-pyrimidin-4-ylsulfanyl)-4-methoxy-phenyl]-2,4,6-trimethyl -benzenesulfonamide(5.29 g, 0.01 mol) with piperidine (0.86 g, 0.01) 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 82%, m.p. 460–462 K).