Methyl c-1-cyano-t-2-methylsulfonyl-3-phenylcyclopropanecarboxylate

The title compound, C13H13NO4S, is a racemic mixture of enantiomers. Short intramolecular contacts between sulfonyl O and ester carbonyl C atoms are observed [C⋯O = 2.881 (1), 2.882 (1) and 2.686 (1) Å], indicating the possibility of donor—acceptor interactions between these groups. The dihedral angle between the phenyl and cyclopropyl rings is 79.3 (1)°.

In compound (2) three short intramolecular contacts C···O, which appreciable less sum of the van der Vaals radii given atoms = 3.000Å (Zefirov et al., 1989), are found out. The first of them takes place between atoms O2 of sulfonyl and C5 of methoxycarbonyl groups (2.881 Å). The second contact length 2.882Å is observed between atoms O4 of methoxycarbonyl and C10 of cyclopropane fragment. The third is shorted (2.686 Å). It arises between atoms O1 of methoxycarbonyl group and C2 of cyano group. Given contacts are evidence of possible donor-acceptor interaction between cys-located sulfonyl and methoxycarbonyl groups, and also between methoxycarbonyl on the one hand,cyano group and cyclopropene fragment -with another.
We shall note, that strong interaction between drawing together sulfonyl and methoxycarbonyl groups in structure of cyclobutane fragment, hardly fixed in space by trimethylene bridge, where free rotation of given groups was revealed earlier; interatomic distance C···O in this case is 2. 489Å (Vasin et al., 2010). At the same time, in analogue of compound (2) -dimethyl 3-phenyl-2-(t)-phenylsulfonyl-1,1-cyclopropanecarboxylate, as it has been established by X-ray analysis, mutual, close to parallel, an arrangement of sulfonyl and ethoxycarbonyl groups the dipole-dipole interaction between them does not promote (Yamamoto et al., 1985).
The structure of compound (2) consists of separate molecules between which only van der Vaals interaction is carried out.

Experimental
Compound (2) was obtained by the reaction between the previously reported compound (1) (Vasin et al., 2008) and monosodium salt of methyl cyanoacetate (see Fig. 2). Sodium hydride (0.23 g 60% suspension in mineral oil) was freed of mineral oil by washing with hexane and was added dry THF (5 ml). Methyl cyanoacetate (4.2 g) in THF (10 ml

Refinement
The initial fragment of structure was solved by a direct method; other non-hydrogen atoms were received from the analysis by successive synthesis of electron density. Floating origin restraint had been used. Hydrogen atoms were placed in geometrically calculated positions and refined in riding model with U (H) = 1.5 U (C) for hydrogen atoms in methyl groups and U (H) = 1.2 U (C) for all other hydrogen atoms, where U (C) -the equivalent temperature factor of carbon atom with which the corresponding hydrogen atom is bonded. Figures   Fig. 1. A view of the compound (2). The non-H atoms are shown with displacement ellipsoids drawn at the 50% probability level.
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 Refinement. The one restraint corresponded to floating origin restraints. 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.