4-Amino-12-methylsulfonyloxy-[2.2]paracyclophane

The title compound, C17H19NO3S, was synthesized from 4-benzhydrylideneamino-12-hydroxy-[2.2]paracyclophane and methanesulfonyl chloride. In the molecule, the distance between the centroids of two aromatic rings is 2.960 (5) Å. In the crystal, weak N—H⋯O and C—H⋯O hydrogen bonds link the molecules into layers parallel to the ac plane.


Comment
Since the first synthesis of [2.2]paracyclophane (Cram, 1959), its structure atrracted considerable interest (Liebman et al., 1976;Dyson et al., 1998). [2.2]Paracyclophane needs only one substituent to become planar chiral, so, there has been notable progress with regard to the synthesis of new derivatives and their applications in asymmetric catalysis (Hou et al., 2000;Duan et al., 2008).
In the title compound ( Fig. 1), all bond lengths and angles are normal and in agreement with those observed in the related structure (Ma et al., 2012). In the molecule, the distance between the centroids of two aromatic rings is 2.960 (5) Å. The crystal packing exhibits weak intermolecular N-H···O and C-H···O hydrogen bonds (Table 1), which link the molecules into layers parallel to the ac plane.

Experimental
The title compound was prepared by the method reported by Duan et al. (2012). The crystals were obtained by recrystallization from hexane and ethyl acetate.

Refinement
All the H atoms were located in difference maps, but placed in idealized positions (N-H 0.86 Å, C-H 0.93-0.97 Å), and refined as riding, with with U iso (H) = 1.2-1.5 U eq of the parent atom.  The molecular structure of the title compound showing the atom-numbering scheme and 50% probability displacement ellipsoids.

4-Amino-12-methylsulfonyloxy-[2.2]paracyclophane
Crystal data C 17 H 19 NO 3 S M r = 317.39 Orthorhombic, P2 1 2 1 2 1 Hall symbol: P 2ac 2ab a = 8.017 (7)  where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.15 e Å −3 Δρ min = −0.23 e Å −3 Absolute structure: Flack (1983), 1122 Friedel pairs Absolute structure parameter: 0.02 (9) Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.