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

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

doi:10.1107/S1600536812033375

. 2012 Jul 28;68(Pt 8):o2590–o2591. doi: 10.1107/S1600536812033375

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

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

PMCID: PMC3415028 PMID: 22905015

Abstract

In the title compound, C₂₂H₂₃BrN₄O₄S₂, the benzene rings bridged by the sulfonamide group are tilted relative to each other by 68.9 (1)° and the dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 69.7 (1)°. The molecular conformation is stabilized by a weak intramolecular π–π stacking interaction between the pyrimidine and the 4-methylbenzene rings [centroid–centroid distance = 3.934 (2) Å]. The morpholine ring adopts a chair conformation and is disordered over two positions with an occupancy ratio of 0.853 (6):0.147 (6). In the crystal, molecules are linked by N—H⋯O hydrogen bonds into chains extending along the a axis and further, through C—H⋯N and C—H⋯O interactions, into a three-dimensional supramolecular structure.

Related literature

For the crystal structures of sulfonamides, see: Rodrigues et al. (2011 ▶); Akkurt et al. (2011 ▶). For their biological activity, see: Gao & Pederson (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring asymmetry parameters and conformations, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C₂₂H₂₃BrN₄O₄S₂
M _r = 551.47
Monoclinic,
a = 10.0321 (3) Å
b = 17.4842 (6) Å
c = 13.9095 (4) Å
β = 91.699 (3)°
V = 2438.70 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.89 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.557, T _max = 1.000
21500 measured reflections
4783 independent reflections
3361 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.086
S = 1.01
4783 reflections
321 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.46 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/S1600536812033375/gk2516sup1.cif

e-68-o2590-sup1.cif^{(35.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033375/gk2516Isup2.hkl

e-68-o2590-Isup2.hkl^{(229.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812033375/gk2516Isup3.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⋯O26A ⁱ	0.85 (2)	2.02 (2)	2.846 (8)	163 (2)
N8—H8⋯O26B ⁱ	0.85 (2)	2.06 (6)	2.895 (5)	165 (3)
C21—H21⋯N20ⁱⁱ	0.93	2.53	3.394 (4)	155
C25A—H251⋯O2ⁱⁱⁱ	0.97	2.59	3.377 (6)	138
C27A—H272⋯O2ⁱⁱⁱ	0.97	2.52	3.341 (6)	143

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

Acknowledgments

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

The amide and sulfonamide moieties are the constituents of many biologically significant compounds. Sulfonamide compounds are well known as antimicrobial agents (Gao & Pederson, 2005). In the present work, the crystal structure of N-[2-(5-bromo-2-morpholin-4-yl-pyrimidin-4-ylsulfanyl)-4-methoxy-phenyl]-4- methyl-benzenesulfonamide has been determined.

Bond lengths and angles in the title compound (Fig. 1) have normal values (Allen et al., 1987) and are comparable with the similar crystal structures (Rodrigues et al., 2011; Akkurt et al., 2011). The morpholine ring is disordered over two positions with the occupancy ratio of 0.853 (6):0.147 (6) and adopts chair conformation (asymmetry parameters:ΔC_s(C24A—C27A) = 1.30; ΔC₂(C24A—C25A) = 1.59; ΔC_s(C25B—C28B) = 2.37; ΔC₂(C25B—O26B) = 3.65 (Duax & Norton, 1975). The two benzene rings are tilted relative to each other by 68.9 (1)°. The dihedral angle formed by the pyrimidine ring with two benzene rings (C9—C14/C1—C6) are 69.7 (1) and 2.2 (1)°, respectively. In the crystal, molecules are connected via N—H···O, C—H···N and C—H···O hydrogen bonds.

Experimental

The reaction of N-[2-(5-bromo-2-chloro-pyrimidin-4-ylsulfanyl)-4-methoxy-phenyl]- 4-methyl-benzenesulfonamide (5.01 g, 0.01 mol) with morpholine (0.88g, 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 the residue was extracted with ethyl acetate. The compound was purified by successive recrystallization from methanol (yield 84%, m.p. 485-487 K).