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

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

doi:10.1107/S1600536812036689

. 2012 Aug 31;68(Pt 9):o2800. doi: 10.1107/S1600536812036689

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

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

PMCID: PMC3435827 PMID: 22969673

Abstract

In the title compound, C₂₁H₂₀BrClN₄O₄S₂, the benzene rings bridged by the sulfonamide group are tilted relative to each other by a dihedral angle of 70.2 (1)° and the dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 69.5 (1)°. The molecular conformation is stabilized by a weak intramolecular π–π stacking interaction between the pyrimidine and the 4-chlorobenzene rings [centroid–centroid distance = 3.978 (2) Å]. The morpholine ring adopts a chair conformation. In the crystal, molecules are linked into inversion dimers by pairs of C—H⋯N hydrogen bonds and these dimers are further connected by N—H⋯O hydrogen bonds, forming a tape along the a axis.

Related literature

For related structures of sulfonamides, see: Rodrigues et al. (2011 ▶); Akkurt et al. (2011 ▶); Kant et al. (2012 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring conformations, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C₂₁H₂₀BrClN₄O₄S₂
M _r = 571.89
Monoclinic,
a = 10.0311 (3) Å
b = 17.3096 (6) Å
c = 13.9223 (4) Å
β = 91.829 (3)°
V = 2416.16 (13) Å³
Z = 4
Mo Kα radiation
μ = 2.02 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 = 0.438, T _max = 0.668
26979 measured reflections
4744 independent reflections
3408 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.117
S = 1.03
4744 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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/S1600536812036689/is5183sup1.cif

e-68-o2800-sup1.cif^{(29.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036689/is5183Isup2.hkl

e-68-o2800-Isup2.hkl^{(227.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812036689/is5183Isup3.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
N7—H7⋯O25ⁱ	0.86	2.09	2.849 (4)	148
C20—H20⋯N19ⁱⁱ	0.93	2.52	3.352 (5)	149

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

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) have normal values (Allen et al., 1987) and are comparable with the similar crystal structures (Rodrigues et al., 2011; Akkurt et al., 2011; Kant et al., 2012). The molecule is twisted at atom S1 with a C1—S1—N7—C8 torsion angle of 60.8 (3)°. The morpholine ring is exhibiting a chair conformation [asymmetry parameters are: ΔC2(N22—C23) = 2.53; ΔCs(N22—O25) = 1/5; Duax & Norton, 1975]. The two benzene rings (C1—C6/C8—C13) are tilted relative to each other by 70.2 (1)° and the dihedral angle between the sulfur bridged pyrimidine and benzene rings is 69.5 (1)°. The molecular conformation is stabilized by a weak intramolecular stacking interaction between the pyrimidine and the 4-chloro benzene rings [centroid–centroid distance = 3.978 (2) Å, interplanar spacing = 3.340 Å, and centroid shift = 2.16 Å]. In the crystal, molecules are linked into dimers by pairs of C20—H20···N19 hydrogen bonds and these dimers are further linked by N7—H7···O25 hydrogen bonds (Table 1 and Fig. 2).

Experimental

The reaction of N-[2-(5-bromo-2-chloro-pyrimidin-4-ylsulfanyl)-4-methoxy-phenyl]-4-chloro-benzenesulfonamide (5.22 g, 0.01 mol) with morpholine (0.88 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 80%, m.p. 462–464 K)