Ethyl N-(2-acetyl-3-oxo-1-phenylbutyl)carbamate

In the title compound, C15H19NO4, all three carbonyl groups are syn-oriented with respect to the methine group attached to the phenyl ring. The mean planes of the phenyl ring and ethyl carbamate moiety form a dihedral angle of 65.2 (1)°. In the crystal, molecules related by translation in [100] are linked into chains via N—H⋯O hydrogen bonds.

In the title compound, C 15 H 19 NO 4 , all three carbonyl groups are syn-oriented with respect to the methine group attached to the phenyl ring. The mean planes of the phenyl ring and ethyl carbamate moiety form a dihedral angle of 65.2 (1) . In the crystal, molecules related by translation in [100] are linked into chains via N-HÁ Á ÁO hydrogen bonds.

Related literature
For details of the synthesis, see: Kuzmina et al. (2013). For the crystal structures of related compounds, see: Hatano et al.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2414).

Comment
Recently, we have developed a simple general five-step approach for the synthesis of macrocycles containing semicarbazide moieties via heterocyclization of semicarbazides with oxo group in 3 position (Kuzmina et al., 2013). The title compound, I, has been obtained as an intermediate product. Herewith we present its molecular and crystal structure.
In the crystal, the molecules related by translation in [1 0 0] are linked into chains via intermolecular classical N-H···O hydrogen bonds (Table 1, Fig. 2).

Refinement
Atom H1 was located on a difference map and isotropically refined. C-bound H atoms were positioned geometrically (C-H = 0.93Å-0.98Å) and refined as riding, with U iso (H) = 1.2-1.5U eq (C).

and
Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).   Portion of the crystal packing in I. Dotted blue lines denote hydrogen bonds. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.30 e Å −3 Δρ min = −0.19 e Å −3 Extinction correction: SHELXL97 (Sheldrick, 2008), Fc * =kFc[1+0.001xFc 2 λ 3 /sin(2θ)] -1/4 Extinction coefficient: 0.009 (2) 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 e.s.d.'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 > 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.