(2S,3R)-tert-Butyl N-[4-(N-benzyl-4-fluoro-benzene-sulfonamido)-3-hy-droxy-1-phenyl-butan-2-yl]carbamate

Abstract

In the title mol-ecule, C(28)H(33)FN(2)O(5)S, the mean plane about the tertiary amine group (sum of the angles subtended at the sp(2)-hybridized N atom = 359.7°) forms a dihedral angle of 16.66 (6)° with the phenyl ring adjacent to the carbamate group. The sulfonamide benzene ring and the hy-droxy group lie to either side of the C(2)NS plane, whereas the benzyl-phenyl (connected to the N atom) and carbamate substituents lie to the other side. Supra-molecular layers propagating in the ac plane are found in the crystal, linked by hy-droxy-sulfonamide O-H⋯O and carbamate-carbamate N-H⋯O hydrogen bonds along with C-H⋯O and C-H⋯π inter-actions.

Fig. 1.

Reaction scheme for the synthesis of the title compound, 3.

Fig. 2.

The molecular structure of 3 showing displacement ellipsoids at the 50% probability level.

Fig. 3.

A view of the supramolecular layer in in the ac plane (I) in 3. The O—H···O, N—H···O, C—H···O and C—H···π interactions are shown as orange, blue, brown and purple dashed lines, respectively.

Fig. 4.

A view in projection down the c axis of the stacking of supramolecular layers in 3 along the b axis. The O—H···O, N—H···O, C—H···O and C—H···π interactions are shown as orange, blue, brown and purple dashed lines, respectively.