SUPRAMOLEKULSKA ORGANIZACIJA 3-(4-HLORBENZOIL)-1,3-DIAZASPIRO[4.5]DEKAN-2,4-DIONA

Abstract

Sintetisan je derivat cikloheksan-5-spirohidantoina i određena je njegova kristalna struktura. Hijerarhijski razvoj kristalnog pakovanja diskutovan je sa aspekta kooperativnosti dimernih motiva koji nastaju preko različitih intermolekulskih interakcija, i to: jakih N–H···O vodoničnih veza i slabih C–H···O, C–H···Cl i C–H···π interakcija. Kristalno pakovanje zadržava motiv, koji se obično sreće kod derivata hidantoina, u kome su dva inverzano orijentisana molekula povezana parom N–H···O vodoničnih veza (slika 1). Specifična strukturna karakteristika jesu paralelni slojevi duž ac-ravni (slika 2). Pošto ovaj motiv povezuje svaki drugi sloj, rastojanje između slojeva se naizmenično menja. Naknadna analiza Hiršfeldove površine omogućila je razradu kvalitativnih i kvantitativnih doprinosa intermolekulskih interakcija proučavanom kristalnom pakovanju. Kristalografski podaci 3-(4-hlorbenzoil)-1,3-diazaspiro[4.5]dekan-2,4-diona: C15H15ClN2O3, Mr = 306.7, trikliničan sistem, prostorna grupa P–1, a = 6,2836(13), b = 10,928(2), c = 12,159(2) Å,  = 108,19(3),  = 99,76(3),  = 104,73(3) °, V = 738,4(3) Å3 , Z = 2, F(000) = 320, ρx = 1,380 g cm–3 , μ(Mo Kα) = 0,270 mm–1 . Utačnjavanje sa F 2 (190 parametara) dalo je R1 = 0,0821, wR2 = 0,1157, S = 1,031 za sve podatke i R1 = 0,0548 za 2707 uočenih refleksija sa I ≥ 2σ(I).

A derivative of cyclohexane-5-spirohydantoin was synthesized and its crystal structure was determined. The hierarchical development of the crystal packing was discussed through cooperativity of various dimeric motifs associated with the presence of different intermolecular interactions, namely strong N–H···O, and weaker C–H···O, C–H···Cl and C–H···π interactions. The crystal packing retained the motif commonly found in hydantoin derivatives where two molecules related by inversion are linked by a pair of N–H∙∙∙O hydrogen bonds (Figure 1). A hallmark structural feature was a parallel layer arrangement to the ac-plane (Figure 2) with alternating perpendicular separation, whereby this motif connect every second layer. An analysis of the Hirshfeld surface further elaborated the qualitative and quantitative contributions of intermolecular interactions to the crystal packing. Crystal data for 3-(4-chlorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione: C15H15ClN2O3, Mr = 306.7, triclinic system, space group P–1, a = 6.2836(13), b = 10.928(2), c = 12.159(2) Å,  = 108.19(3),  = 99.76(3),  = 104.73(3) °, V = 738.4(3) Å3 , Z = 2, F(000) = 320, ρx = 1.380 g cm–3 , μ(Mo Kα) = 0.270 mm–1 . The refinement on F 2 (190 parameters) yielded R1 = 0.0821, wR2 = 0.1157, S = 1.031 for all data, and R1 = 0.0548 for 2707 observed reflections with I ≥ 2σ(I).