Crystal structure of 2-benzoyl-3-(4-chlorophenyl)cyclopropane-1,1- dicarbonitrile, C18H11ClN2O

Abstract

Source of materialAmixture of triphenylarsine (0.167 g, 0.15 mmol), phenacyl bromide (0.238 g, 1.2mmol), 2-(4-chlorobenzylidene)malononitrile (1 mmol), and NaHCO 3 (0.240 g, 3mmol) was stirred in CH 3 CN at room temperature. The progress of the reaction was monitored by thin-layer chromatography (TLC). Afterc ompletion, water was added and the product was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to afford the crude product. Colourless crystals of the title compound, suitablefor X-rayanalysis were obtained by recrystallizingfrom amixture of methylene chloride and ethylacetateatroom temperature. Experimental detailsThe hydrogen atoms were located by geometrically calculations, andtheir positionsand thermal parameters were fixed during the structurerefinement. DiscussionThe synthesis and application of multisubstituted cyclopropanes have been subjects of greati nterestb ecause of ther oles of cycloprapanesasbasic structural elements in awide rangeofbiologicallya ctivec ompounds and important intermediates in organic synthesis [1-3]. As part of our work, we report the synthesis and crystal structure of the title compound. Within the crystal structure, theg eometricp arameters of cyclopropane arei nt he usual ranges. The C8-C10, and C9-C10 bond lengths are 1.550(2), 1.544(2) Å, respectively. TheC 8-C9 bond length is 1.492(2), slightly shorter than the other two C-C bonds. The bond angles of C9-C8-C10, C8-C9-C10a nd C8-C10-C9a re 60.96(10)°, 61.40(10)°and 57.64(9)°, showing the angles of ca. 60°the benzoyl and aryl groups are situated in an "E" configuration at the cyclopropane ring.