2017. 58, 2 UDC 541.6:547.12 STRONG HYDROGEN BONDED SUPRAMOLECULAR ARCHITECTURE IN A CRYSTAL OF THE {3-[2-(1,3-BENZODIOXOL-5-YL)-7-METHOXY1-BENZOFURAN-5-YL] PROPYL} DIETHYLAMINE CATION WITH THE HYDROGEN BONDED CHLORIDE HYDRATE ANION (HALIDES) ASSEMBLY: X-RAY STRUCTURE, DFT CALCULATIONS, HIRSHFELD SURFACE ANALYSIS G. Yakalı1, S.E. Цztьrk2, M. Aygьn3 1Department of Opticianry, Vocational School of Higher Education, Akdeniz University, Antalya, Turkey E-mail: gulyakali@akdeniz.edu.tr 2Department of Chemistry, Faculty of Sciences, Ege University, zmir, Turkey 3Department of Physics, Faculty of Sciences, Dokuz Eylьl University, zmir Turkey Received November, 8, 2015 A hydrogen bonded chloride hydrate assembly {[(H2O)Cl]}– is ion-countered by organic molecular [C23H28NO4]+ cations and the crystal structure of {3-[2-(1,3-benzodioxol-5-yl)7-methoxy-1-benzofuran-5-yl] propyl} diethylamine [C23H28NO4]+[H2OCl]– is synthesized. <...> Its structure is studied using X-ray crystallography. <...> The molecular geometrical parameters, frontier molecular orbital energies (HOMO, LUMO), their energy gap (9E), molecular electrostatic potential analysis of the compound are calculated by DFT/B3LYP at the 6-311G(d,p) level. <...> Benzofuran and benzodioxo ring systems of the title compound, except the diethylamine group, are essentially planar and a dihedral angle between the ring systems is 7.38(14). <...> The hydrogen bonded chloride hydrate is self-assembled to form a supramolecular array of strong N—H…Cl and O—H…Cl bifurcated hydrogen bonds making tetramers which consist of a fused four-membered ring with a graph-set descriptor and a pseudo cyclic centrosymmetric 2 R2 (8) ring motif. <...> The supramolecular crystal packing is consolidated by these bifurcated hydrogen bonds and the stacking of the sheet through strong … interactions. <...> Moreover, the chain hydrogen bonds form intermolecular and intramolecular C—H…O hydrogen bonds and the 1D supramolecular array is organized by C—H… interactions. <...> The intercontacts in the crystal structure are analyzed using the Hirshfeld surfaces computational method. <...> The calculated geometrical parameters are in good agreement with the observed single crystal XRD data. <...> DOI: 10.15372/JSC20170212 Keywords: crystal structure, benzofuran, bifurcated hydrogen bond, chloride hydrate, supramolecular architecture <...>