title: Intermolecular interactions of proton transfer compounds: synthesis, crystal structure and Hirshfeld surface analysis.
abstract: Three new proton transfer compounds, [2-ammonio-5-methylcarboxybenzene perchlorate (1), (C8H10NO2(+)·ClO4(-)), 4-(ammoniomethyl)carboxybenzene nitrate (2), (C8H10NO2(+)·NO3(-)), and 4-(ammoniomethyl)carboxybenzene perchlorate (3), (C8H10NO2(+)·ClO4(-))], have been synthesized, their IR modes of vibrations have been assigned and their crystal structures studied by means of single-crystal X-ray diffraction. Their asymmetric units consist of one cation and one anion for both compounds (1) and (2). However, the crystal structure of compound (3) is based on a pair of cations and a pair of anions in its asymmetric unit. The three-dimensional Hirshfeld surface analysis and the two-dimensional fingerprint maps revealed that the three structures are dominated by H...O/O...H and H...H contacts. The strongest hydrogen-bonding interactions are associated with O-H...O and N-H...O constituting the highest fraction of approximately 50%, followed by those of the H...H type contributing 20%. Other close contacts are also present, including weak C...H/H...C contacts (with about 10%).
authors.affiliation: Laboratoire des Structures, Propriétés et Interactions Interatomiques LASPI2A, Département des Sciences de la Matière, Faculté des Sciences et Technologie, Université `Abbes Laghrour', Khenchela 40000, Algeria.
authors.forename: Amani
authors.initials: A
authors.lastname: Direm
authors.affiliation: Istituto di Cristallografia, Via G. Amendola 122/o, Bari 7016, Italy.
authors.forename: Angela
authors.initials: A
authors.lastname: Altomare
authors.affiliation: Istituto di Cristallografia, Via G. Amendola 122/o, Bari 7016, Italy.
authors.forename: Anna
authors.initials: A
authors.lastname: Moliterni
authors.affiliation: Laboratoire des Structures, Propriétés et Interactions Interatomiques LASPI2A, Département des Sciences de la Matière, Faculté des Sciences et Technologie, Université `Abbes Laghrour', Khenchela 40000, Algeria.
authors.forename: Nourredine
authors.initials: N
authors.lastname: Benali-Cherif
keywords: Hirshfeld surface analysis; crystal engineering; graph-set; hydrogen-bonding frameworks; proton-transfer compounds