(2S,3R)-tert-Butyl N-[4-(N-benzyl-4-fluorobenzenesulfonamido)-3-hydroxy-1-phenylbutan-2-yl]carbamate

In the title molecule, C28H33FN2O5S, 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 hydroxy group lie to either side of the C2NS plane, whereas the benzylphenyl (connected to the N atom) and carbamate substituents lie to the other side. Supramolecular layers propagating in the ac plane are found in the crystal, linked by hydroxy–sulfonamide O—H⋯O and carbamate–carbamate N—H⋯O hydrogen bonds along with C—H⋯O and C—H⋯π interactions.

In the title molecule, 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 2hybridized 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 hydroxy group lie to either side of the C 2 NS plane, whereas the benzylphenyl (connected to the N atom) and carbamate substituents lie to the other side. Supramolecular layers propagating in the ac plane are found in the crystal, linked by hydroxy-sulfonamide O-HÁ Á ÁO and carbamate-carbamate N-HÁ Á ÁO hydrogen bonds along with C-HÁ Á ÁO and C-HÁ Á Á interactions.

1.
Compound 3, Fig. 2, the tertiary amine is sp 2 hybridized as evidenced by the sum of the angles subtended at the N1 atom of 359.7°. The sulfonamide-benzene and benzyl-phenyl rings connected to the N1 atom are almost orthogonal to each other, with the dihedral angle between them being 73.86 (11)°, and lie to either side of the C 2 NS plane. The hydroxy group is orientated to the same side of the molecule as the sulfonamide-benzene ring, and the carbamate group to the same side as the benzyl-phenyl ring. The dihedral angle between the carbamate group and adjacent phenyl ring is 66.35 (8)°, with the latter approximately parallel with the C 2 NS plane, forming a dihedral angle of 16.66 (6)°.
In the crystal packing, the hydroxy group forms a hydrogen bond with a sulfonamide-O atom, and the carbamate-N-H and O atoms self-associate, Table 1. These interactions are reinforced by C-H···O and C-H···π interactions, Table 1, to form a supramolecular layer in the ac plane, Fig. 3. Layers stack along the b axis with no specific intermolecular interactions between them, Fig. 4.

Refinement
The C-bound H atoms were geometrically placed (C-H = 0.95-1.00 Å) and refined as riding with U iso (H) = 1.2-1.5U eq (C). The O-bound H-atom was located in a difference Fourier map and refined with an O-H restraint of 0.84±0.01 Å, and with U iso (H) = 1.5U eq (O); the N-H H-atom was treated similarly with N-H = 0.88±0.01 Å and with U iso (H) = 1.2U eq (N).

Figure 2
The molecular structure of 3 showing displacement ellipsoids at the 50% probability level.    Special details Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.