Crystal stucture of methyl 2-({[2-(methoxycarbonyl)phenyl]carbamoyl}amino)benzoate

In the title compound, C17H16N2O5, the dihedral angles between the central urea [N—C(=O)—N] fragment and its attached benzene rings are 20.20 (14) and 24.24 (13)°; the dihedral angle between the aromatic rings is 42.1 (1)°. The molecular conformation is consolidated by two intramolecular N—H⋯O hydrogen bonds, which both generate S(6) rings. In the crystal, inversion dimers linked by pairs of C—H⋯O interactions generate R 2 2(14) loops. The dimers are linked by further C—H⋯O interactions into (011) sheets.

Symmetrical disubstituted ureas generally form a polar hydrogen-bond chain, with anti NH donors and carbonyl O-atom acceptors in a bifurcated motif. As part of our studies in this area, the title compound C 17 H 16 N 2 O 5 was synthesized and its crystal structure is reported in the present work.
The molecular structure of the title compound, a symmetrical urea derivative, is displayed in Fig. 1. This molecule is build up from two methyl benzoate linked through N-C(=O)-N fragment but not symmetric. The dihedral angle between the two phenyl rings (C3 to C8) and (C10 to C15) is of 42.1 (1)°.
In the crystal, the molecular conformation is stabilized by two intramolecular N-H···O hydrogen bonds and each molecule is linked to its symmetric by two intermolecular C-H···O hydrogen bonds to form centrosymmetric dimers as shown in Fig.2.

S3. Refinement
All H atoms could be located in a difference Fourier map. However, they were placed in calculated positions with C-H = 0.93-0.96 Å; N-H = 0.86 Å, and refined as riding on their parent atoms with U iso (H) = 1.2 U eq for aromatic, C-H, N-H and U iso (H) = 1.5 U eq for methyl. Two outlier (1 0 0) and (0 2 0) was omitted in the last cycles of refinement.

Figure 1
A view of the molecule of the title compound, showing displacement ellipsoids drawn at the 50% probability level.

Figure 2
Part of the crystal structure of the title compound, showing hydrogen-bonded (dashed lines) dimers.

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.