Crystal structure of 2-benzoyl-3-(4-methylphenyl)cyclopropane-1,1- dicarbonitrile, C19H14N2O

Abstract

C 19 H 14 N 2 O, triclinic, P1 (no.2), a =8.138(2) Å, b =10.434(2)Å,c=11.109(2)Å,a=99.678(5)°, b =111.028(4)°, g =112.769(5)°, V =758.5 Å 3 , Z =2, Source of materialAmixture of triphenylarsine (0.167 g, 0.15 mmol), phenacyl bromide (0.238 g, 1.2m mol), 2-(4-methylbenzylidene)malononitrile (1 mmol),and NaHCO 3 (0.240 g, 3mmol) wasstirred in CH 3 CN at room temperature. The progress of reaction was monitored by thin-layer chromatography (TLC). Afterc ompletion, water was added and the product was extracted with ethyl acetate. Theo rganic layerw as separated, driedo vera nhydrous sodium sulfate, andthe solventwas evaporated underreduced pressure to afford thec rude product. Colourless crystalso ft he titlec ompound, suitable for X-ray analysis, were obtained by recrystallizing from amixture of methylene chloride and ethylacetate at room 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 cycloprapanes as basic structural elements in awide rangeofbiologicallya ctivec ompounds andi mportant 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, thegeometricparameters of cyclopropane arein theu sual ranges.T he C8-C9a nd C9-C10 bond lengthsa re 1.542(2),1 .544(2) Å, respectively. TheC8-C10 bond length is 1.489(2), slightly shorter than the two other C-C bonds. The bond angleso fC 9-C8-C10, C8-C9-C10 and C8-C10-C9a re 61.22(10)°, 57.68(10)°and 61.1(9)°,only slightly deviating from the ideal 60°angle. By analogy with th E-, Z-nomenclature the compound has an E configuration at the C8-C10 unit.