N-(2-{[5-Bromo-2-(piperidin-1-yl)pyrimidin-4-yl]sulfan-yl}-4-meth-oxy-phen-yl)benzene-sulfonamide

Abstract

The title compound, C(22)H(23)BrN(4)O(3)S(2), crystallizes with two mol-ecules, A and B, in the asymmetric unit. In one of these, the meth-oxy group is disordered over two sets of sites in a 0.565 (9):0.435 (9) ratio. The benzene rings bridged by the sulfonamide group are tilted relative to each other by 37.4 (1) and 56.1 (1)° in mol-ecules A and B, respectively, while the dihedral angles between the sulfur-bridged pyrimidine and benzene rings are 72.4 (1) and 70.2 (1)° for A and B, respectively. The piperidine ring adopts a chair conformation in both mol-ecules. In the crystal, inversion dimers linked by pairs of N-H⋯N hydrogen bonds occur for both A and B; the dimers are linked into [010] chains by C-H⋯O hydrogen bonds. The crystal structure also features inversion-generated aromatic π-π stacking inter-actions between the pyrimidine rings for both mol-ecules [centroid-centroid distances = 3.412 (2) (mol-ecule A) and 3.396 (2) Å (mol-ecule B)].

Fig. 1.

The molecular structure with displacnent ellipsoids drawn at the 40% probability level.

Fig. 2.

Dimer formation between the molecules.

Fig. 3.

A molecular packing view of the title compound down the a axis, showing intermolecular interactions. For clarity, hydrogen atoms which are not involved in hydrogen bonding have been omitted.