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Isonicotinamide-2-naphthoic acid (1/1).

ABSTRACT: In the title 1:1 adduct, C(6)H(6)N(2)O·C(11)H(8)O(2), the amide group is slightly twisted out of the plane of the aromatic ring, with a C-C-C-N torsion angle of 25.11?(19)°, whereas the carb-oxy-lic acid group is approximately coplanar with the bicylic ring system, with a C-C-C-O torsion angle of 10.9?(2)°. The amide groups from two isonicotinamide mol-ecules form a dimer via N-H?O hydrogen bonds. In addition, the 2-naphthanoic acid mol-ecule is hydrogen bonded to the pyridine unit of an isonicotinamide mol-ecule via an O-H?N hydrogen bond. This gives rise to a centrosymmetric four-mol-ecule chain, which is cross-linked by further N-H?O hydrogen bonds from the amide group.

SUBMITTER: Madeley LG

PROVIDER: S-EPMC3239073 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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Isonicotinamide-2-naphthoic acid (1/1).

Madeley Lee G LG Levendis Demetrius C DC Lemmerer Andreas A

Acta crystallographica. Section E, Structure reports online 20111125 Pt 12

In the title 1:1 adduct, C(6)H(6)N(2)O·C(11)H(8)O(2), the amide group is slightly twisted out of the plane of the aromatic ring, with a C-C-C-N torsion angle of 25.11 (19)°, whereas the carb-oxy-lic acid group is approximately coplanar with the bicylic ring system, with a C-C-C-O torsion angle of 10.9 (2)°. The amide groups from two isonicotinamide mol-ecules form a dimer via N-H⋯O hydrogen bonds. In addition, the 2-naphthanoic acid mol-ecule is hydrogen bonded to the pyridine unit of an isonico ...[more]

PMID: 22199921

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Project description:The co-crystallization of (benzylthio)acetic acid (HBTA) with L-proline (L-PRO), D-proline (D-PRO), DL-proline (DL-PRO), isonicotinamide (INA) and tryptamine (TPA) led to the formation of five novel crystalline compounds: L-PRO±·HBTA (1), D-PRO±·HBTA (2), DL-PRO±·HBTA (3), INA·HBTA (4) and TPA+·BTA- (5). The prepared supramolecular assemblies were characterized by single crystal X-ray diffraction, an elemental analysis, FT-IR spectroscopy and a thermal analysis based on thermogravimetry (TG) combined with differential scanning calorimetry (DSC). Additionally, their melting points through TG/DSC measurements were established. All fabricated adducts demonstrated the same stoichiometry, displayed as 1:1. The integration of HBTA with selected N-containing co-formers yielded different forms of multi-component crystalline phases: zwitterionic co-crystals (1-3), true co-crystal (4) or true salt (5). In the asymmetric units of 1-4, the acidic ingredient is protonated, whereas the corresponding N-containing entities take either the zwitterionic form (1-3) or remain in the original neutral figure (4). The molecular structure of complex 5 is occupied by the real ionic forms of both components, namely the (benzylthio)acetate anion (BTA-) and the tryptaminium cation (TPA+). In crystals 1-5, the respective molecular residues are permanently bound to each other via strong H-bonds provided by the following pairs of donor···acceptor: Ocarboxylic···Ocarboxylate and Npyrrolidinium···Ocarboxylate in 1-3, Ocarboxylic···Npyridine and Namine···Ocarboxylic in 4 as well as Nindole···Ocarboxylate and Naminium···Ocarboxylate in 5. The crystal structures of conglomerates 1-5 are also stabilized by numerous weaker intermolecular contacts, including C-H···O (1-3, 5), C-H···S (1, 2, 5), C-H···N (5), C-H···C (5), C-H···π (1-5) as well as π···π (4) interactions. The different courses of registered FT-IR spectral traces and thermal profiles for materials 1-5 in relation to their counterparts, gained for the pure molecular ingredients, also clearly confirm the formation of new crystalline phases.

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Isonicotinamide-2-naphthoic acid (1/1).

Publications

Isonicotinamide-2-naphthoic acid (1/1).

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