2-[(Phenylcarbamoyl)amino]butyl N-phenylcarbamate

In the title compound, C18H21N3O3, the terminal phenyl rings make a dihedral angle of 86.3 (5)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into chains along [001], forming parallel C(4) and R 1 2(6) graph-set motifs.

In the title compound, C 18 H 21 N 3 O 3 , the terminal phenyl rings make a dihedral angle of 86.3 (5) . In the crystal, molecules are linked by N-HÁ Á ÁO hydrogen bonds into chains along [001], forming parallel C(4) and R 1 2 (6) graph-set motifs.  Table 1 Hydrogen-bond geometry (Å , ). Carbamides and carbamates are great classes of organic compounds due to their incorporations in many of bioactive structures. Carbamides, such as N-phenyl-N′-(2-chloroethyl)ureas (CEUs) and benzoylureas (BUs) show good anticancer activity, and these compounds have mainly been proved to be tubulin ligands that inhibit the polymerization of tubulin (Li et al., 2009;Gisbert et al., 2004). Carbamates such as aldicarb, carbofuran (Furadan), carbaryl (Sevin), ethienocarb, and fenobucarb are widely used as active pesticides (Metcalf, 2002). Carbamates used also in drug design of anticancer drugs (Ray & Chaturvedi, 2004) and in polymer industry such as polyureathanes. In view of such important applications, we herein report the synthesis and crystal structure of the title compound (I) having both functions of carbamide and carbamate groups.

Experimental
The title compound was obtained as a biproduct from a reaction mixture of 89 mg (1 mmol

Refinement
Carbon-bound H-atoms were placed geometrically (C-H = 0.93 to 0.98 Å) and were refined using a riding model with U iso =1.2 or 1.5U eq (C). The N-bound H atom was located from a difference map and refined freely with the distance restraint N-H = 0.86 ± 0.02 Å. In the absence of significant anomalous scattering, the absolute configuration could not  Farrugia, 1999) and PLATON (Spek, 2009).

Figure 1
View of (I) with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.

Figure 2
The crystal packing and hydrogen bonding of (I) down the a axis. H atoms not involved in hydrogen bonds have been omitted for clarity.  (5) Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs 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.