@conference{
author = "Trišović, Nemanja and Radovanović, Lidija and Janjić, Goran V. and Jelić, Stefan T. and Rogan, Jelena",
year = "2019",
abstract = "Sintetisana su dva derivata fenitoina (5,5-difenilhidantoina) i određene su
njihove kristalne strukture. Urađena je kvantitativna analiza kristalnog
pakovanja sa aspekta međumolekulskih interakcija i strukturnih motiva.
Kristalno pakovanje 3-izopropil-5,5-difenilhidantoina sadrži
centrosimetrične dimere povezane parom N–H∙∙∙O vodoničnih veza koji se dalje
umrežavaju pomoću C–H∙∙∙O interakcija i paralelnih interakcija između fenilnih
prstenova na velikom rastojanju u lance paralelne s-osi (slika 1). Osnovna
karakteristika kristalne strukture 3-ciklopropil-5,5-difenilhidantoina jesu
lanci koji nastaju preko N–H∙∙∙O vodoničnih veza, C–H∙∙∙O i C–H∙∙∙π interakcija
(slika 2). Predstavljeno istraživanje daje uvid u ulogu međumolekulskih interakcija u
kristalnom pakovanju proučavanih jedinjenja, kao i dalje smernice za dizajniranje
novih derivata fenitoina sa poboljšanim farmaceutskim svojstvima. Strukturni podaci 3-izopropil-5,5-difenilhidantoina: C18H18N2O2,
trikliničan sistem, prostorna grupa P–1, a = 8,5357(9), b = 8,6225(8),
c = 12,3979(9) Å, α = 104,010(7), β = 91,826(7), γ = 115,201(10) °, V = 791,54(14) Å3
,
R1 = 0,0473.
Strukturni podaci3-ciklopropil-5,5-difenilhidantoina: C18H16N2O2,
monokliničan sistem, prostorna grupa P21/c, a = 11,5996(5), b = 10,6459(3),
c = 12,2992(5) Å, β = 101,977(4) °, V = 1485,74(10) Å3
, R1 = 0,0403., Two derivatives of phenytoin (5,5-diphenylhydantoin) were synthesized and their crystal
structures were determined. The quantitative analysis of the crystal packings in terms of the
contributing intermolecular interactions and structural motifs has been done. The crystal packing of 3-isopropyl-5,5-diphenylhydantoin contains centrosymmetric dimers linked by paired
N–H∙∙∙O hydrogen bonds which further self-organize through pairs of C–H∙∙∙O interactions and
a parallel interaction of two phenyl rings at a large offset into chains running along the c-axis
(Figure 1). The principal feature of the crystal structure of 3-cyclopropyl-5,5-
diphenylhydantoin is formation of the chains by N–H∙∙∙O hydrogen bonds, C–H∙∙∙O and C–
H∙∙∙π interactions (Figure 2). The presented investigation provide not only new insight into the
role of intermolecular interactions in the crystal packing, but also guidance for furthering
crystal engineering to design novel hydantoin derivatives with improved pharmaceutical
properties. Crystal data for 3-isopropyl-5,5-diphenylhydantoin: C18H18N2O2, triclinic, P–1,
a = 8.5357(9), b = 8.6225(8), c = 12.3979(9) Å, α = 104.010(7), β = 91.826(7),
γ = 115.201(10) °, V = 791.54(14) Å3
, R1 = 0.0473.
Crystal data for 3-cyclopropyl-5,5-diphenylhydantoin: C18H16N2O2, monoclinic, P21/c,
a = 11.5996(5), b = 10.6459(3), c = 12.2992(5) Å, β = 101.977(4) °, V = 1485.74(10) Å3
,
R1 = 0.0403.",
publisher = "Beograd : Srpsko kristalografsko društvo",
journal = "Izvodi radova / XXVI konferencija Srpskog kristalografskog društva, Srebrno jezero, 27–28. jun 2019",
title = "ULOGA MEĐUMOLEKULSKIH INTERAKCIJA U KRISTALNOM PAKOVANjU 3-IZOPROPIL I 3-CIKLOPROPIL DERIVATA FENITOINA, THE ROLE OF INTERMOLECULAR INTERACTIONS IN THE CRYSTAL PACKING OF 3-ISOPROPYL AND 3-CYCLOPROPYL DERIVATIVES OF PHENYTOIN",
pages = "31-30",
url = "https://hdl.handle.net/21.15107/rcub_technorep_6706"
}