Crystal structure of ethyl 2-(3-(2-fluorobenzyloxy)ureido)acetate, C12H15FN2O4

Abstract

Source of materialSynthesis of the title compound was accomplished by reaction of glycine ethyl ester hydrochloride (9 mmol) with N-(2-fluorobenzyloxy)-4-nitrophenylester (9 mmol) in dry methylene chloride (60 ml) in the presence of anhydrous triethylamine (18 mmol). The reaction mixture was stirred for 12 hand washed with 1MN aOH, 1MH Cl and water [1]. The organic fraction was dried with MgSO 4 ,filtered, and distilled at the reduced pressure at 25°Ctogive the desired compound as ayellow solid. The substance was recrystallized from purified ethyl ether, filtered, washed with ethyl ether to obtain acolorless solid and dried. Colorless column-shaped single crystals of the title compound suitable for X-ray diffraction analysis were obtained by slow evaporation of the mixed solvent ethanol/water (9:1, v/v)atroom temperature for six days (m.p. 51 -52°C). Experimental details DiscussionThe bond lengths of the carbonyl bonds (C=O) in the title crystal structure are in the normal range of 1.19 -1.23 Å,while the values in the similar hydroxyurea derivatives exceed 1.25 Å [2,3]. There are three significant atomic planes in the structure: (a) benzene ring; (b) the urea plane; (c) O1, O2, C1 and C2 composed plane. The dihedral angle between the ester plane and the benzyl group is obviously smaller (only 3.3(2)°)compared to other hydroxyurea derivatives [4,5]. This may be related to the steric problems between the ester plane and the urea plane, which lead to the urea plane approaches to the benzene ring. The urea plane forms adihedral angle of 81.8(2)°with the ester plane. The complex displays the intermolecular hydrogen bonds along [001] between the N2 and O3 with d(N2-O3) =2.805 Å.

Crystal structure of 1-(4-chlorobenzyloxy)-3-phenylurea, C14H13ClN2O2

“…In the title crystal structure, the bond length of the carbonyl bond (C=O) is 1.225 Å which is in the normal range of 1.19 -1.23 Å, similar to that observed in our previous papers [2][3][4]. There are three significant atomic planes in the structure, two benzene rings and the urea plane (O1, N1, N2, C1).…”

Synthesis, Crystal Structure and in vitro Antitumor Activity of Benzyloxyurea and Benzyloxyhydantoin Derivatives

“…In the hydantoin ring, the length of the carbonyl bond [d(C=O) = 1.194(5) Å and 1.214(5) Å] is in the normal range of 1.19-1.23 Å as well as other hydroxyurea derivatives 6,[13][14][15] . The C-N bond lengths [1.330(5)-1.467(5) Å, mean 1.389(5) Å] are longer than a typical C=N double bond (mean 1.269 Å), (6) but shorter than a C-N single bond [mean 1.443(4) Å], indicating electron delocalization in the hydantoin ring 16 4 and 5.…”