Supramolecular architecture in a co-crystal of the N(7)—H tautomeric form of<i>N</i><sup>6</sup>-benzoyladenine with adipic acid (1/0.5)

Darious, Robert Swinton; Muthiah, Packianathan Thomas; Perdih, Franc

doi:10.1107/s2056989016007581

Cited by 3 publications

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“…Adipic acid (AA) is an industrial chemical used to manufacture nylon and is also used in many drugs and food additives (Rowe et al, 2009). A number of salts and co-crystals involving p-phenylenediamine have been reported (Thakuria et al, 2007;Delori et al, 2016), and adipic acid is also widely known as a coformer in co-crystal formation (Swinton Darious et al, 2016;Lemmerer et al, 2012;Lin et al, 2012;Matulková et al, 2014;Thanigaimani et al, 2012). A 2:1 salt of 4-aminoanilinium (PPDAH) and sebacate, and a 1:1 salt of PPDAH and dihydrogen trimesate have been reported recently (Delori et al, 2016).…”

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confidence: 99%

Crystal structure of a new molecular salt: 4-aminobenzenaminium 5-carboxypentanoate

2018

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The asymmetric unit of the title molecular salt (systematic name: 4-aminoanilinium 5-carboxypentanoate), C 6 H 9 N 2 + ÁC 6 H 9 O 4 À , consists of half a 4-aminobenzenaminium cation (4-ABA) and half a 5-carboxypentanoate anion (5-CP); the other half of each ion is generated by inversion symmetry. Protonation of p-phenylenediamine (PPDA) leads to the formation of a 1:1 salt, but scrutiny of the crystal structure reveals that both of the amine groups of PPDA are partially protonated, with a half-occupied H atom. For the 5-CP anion, an H atom is positioned on an inversion center midway between two O atoms of inversion-related 5-CP ions. In the crystal, the 5-CP anions are linked by the O-HÁ Á ÁO hydrogen bond to form chains propagating along the [110] direction. The chains are linked via N-HÁ Á ÁO and N-HÁ Á ÁN hydrogen bonds involving the 4-ABA cations, forming a three-dimensional supramolecular framework. The title salt was also prepared by mechanochemical synthesis using liquid-assisted grinding (LAG). Its PXRD pattern matches that of the simulated pattern of the crystal structure of the title molecular salt.

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confidence: 99%

Crystal structure of a new molecular salt: 4-aminobenzenaminium 5-carboxypentanoate

2018

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“…Hydrogen-bonding patterns, including base pairing formed by the aminopyrimidines, are important in the structure and functions of nucleic acids (Stanley et al, 2002;Baskar Raj et al, 2003). The hydrogen-bonding patterns present in several aminopyrimidine-carboxylates and cocrystals have been reported by us (Ebenezer et al, 2011;Tamilselvi & Muthiah, 2011;Ebenezer & Muthiah, 2012;Jegan Jennifer & Muthiah, 2014;Karthikeyan et al, 2015;Rajam et al, 2015Rajam et al, , 2017Swinton Darious et al, 2017).…”

Section: Introductionmentioning

confidence: 86%

Design of two series of 1:1 cocrystals involving 4-amino-5-chloro-2,6-dimethylpyrimidine and carboxylic acids

et al. 2018

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Two series of a total of ten cocrystals involving 4-amino-5-chloro-2,6-dimethylpyrimidine with various carboxylic acids have been prepared and characterized by single-crystal X-ray diffraction. The pyrimidine unit used for the cocrystals offers two ring N atoms (positions N1 and N3) as proton-accepting sites. Depending upon the site of protonation, two types of cations are possible [Rajam et al. (2017). Acta Cryst. C73, 862-868]. In a parallel arrangement, two series of cocrystals are possible depending upon the hydrogen bonding of the carboxyl group with position N1 or N3. In one series of cocrystals, i.e. 4-amino-5-chloro-2,6-dimethylpyrimidine-3-bromothiophene-2-carboxylic acid (1/1), 1, 4-amino-5-chloro-2,6-dimethylpyrimidine-5-chlorothiophene-2-carboxylic acid (1/1), 2, 4-amino-5-chloro-2,6-dimethylpyrimidine-2,4-dichlorobenzoic acid (1/1), 3, and 4-amino-5-chloro-2,6-dimethylpyrimidine-2-aminobenzoic acid (1/1), 4, the carboxyl hydroxy group (-OH) is hydrogen bonded to position N1 (O-H...N1) of the corresponding pyrimidine unit (single point supramolecular synthon). The inversion-related stacked pyrimidines are doubly bridged by the carboxyl groups via N-H...O and O-H...N hydrogen bonds to form a large cage-like tetrameric unit with an R(20) graph-set ring motif. These tetrameric units are further connected via base pairing through a pair of N-H...N hydrogen bonds, generating R(8) motifs (supramolecular homosynthon). In the other series of cocrystals, i.e. 4-amino-5-chloro-2,6-dimethylpyrimidine-5-methylthiophene-2-carboxylic acid (1/1), 5, 4-amino-5-chloro-2,6-dimethylpyrimidine-benzoic acid (1/1), 6, 4-amino-5-chloro-2,6-dimethylpyrimidine-2-methylbenzoic acid (1/1), 7, 4-amino-5-chloro-2,6-dimethylpyrimidine-3-methylbenzoic acid (1/1), 8, 4-amino-5-chloro-2,6-dimethylpyrimidine-4-methylbenzoic acid (1/1), 9, and 4-amino-5-chloro-2,6-dimethylpyrimidine-4-aminobenzoic acid (1/1), 10, the carboxyl group interacts with position N3 and the adjacent 4-amino group of the corresponding pyrimidine ring via O-H...N and N-H...O hydrogen bonds to generate the robust R(8) supramolecular heterosynthon. These heterosynthons are further connected by N-H...N hydrogen-bond interactions in a linear fashion to form a chain-like arrangement. In cocrystal 1, a Br...Br halogen bond is present, in cocrystals 2 and 3, Cl...Cl halogen bonds are present, and in cocrystals 5, 6 and 7, Cl...O halogen bonds are present. In all of the ten cocrystals, π-π stacking interactions are observed.

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“…The neutral molecule N 6 -benzoyladenine was first reported by Raghunathan & Pattabhi (1981). Various salts and co-crystals of N 6 -benzoyladenine have also been reported: N 6 -benzoyladenine-3-hydroxypyridinium-2-carboxylate (1:1) and N 6benzoyladenine-dl-tartaric acid (1:1) (Karthikeyan et al, 2015), N 6 -benzoyladeninium nitrate (1:1) (Karthikeyan et al, 2015), N 6 -benzoyladenine-adipic acid (1:0.5) (Swinton Darious et al, 2016). Similarly, various co-crystals of HBA Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Database Surveymentioning

confidence: 98%

“…In the title co-crystal, the N 6 -benzoyladenine also exists in the N(7)-H tautomeric form with non-protonated N1, N3 and N9 atoms. In the crystal structures of N 6 -benzoyladenine (Raghunathan & Pattabhi, 1981), N 6 -benzoyladenine-3-hydroxypyridinium-2-carboxylate (1:1) and N 6 -benzoyl adenine-dl-tartaric acid (1:1) (Karthikeyan et al, 2015), N 6 -benzoyladeninium nitrate (1:1) (Karthikeyan et al, 2016), N 6 -benzoyl adenine-adipic acid (1:0.5) (Swinton Darious et al, 2016) and the title compound (I), the N 6 -substituent is distal to the N1 and syn to the adenine nitrogen atom N7. This may be due to the participation of the N7 atom in N7-H7Á Á ÁO1A intramolecular hydrogen bond (Table 1) with an S(7) ring motif in the Hoogsteen face.…”

Section: Structural Commentarymentioning

confidence: 99%

Supramolecular hydrogen-bonding patterns in a 1:1 co-crystal of the N(7)—H tautomeric form ofN⁶-benzoyladenine with 4-hydroxybenzoic acid

2017

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The asymmetric unit of the title co-crystal contains one molecule of N 6-benzoyladenine (BA) and one molecule of 4-hydroxybenzoic acid (HBA). The N 6-benzoyladenine (BA) has an N(7)—H tautomeric form with non-protonated N-1 and N-3 atoms. This tautomeric form is stabilized by a typical intramolecular N—H⋯O hydrogen bond on the Hoogsteen face of the purine ring. The primary robust (8) ring motif is formed in the Watson–Crick face via N—H⋯O and O—H⋯N hydrogen bonds.

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Supramolecular architecture in a co-crystal of the N(7)—H tautomeric form ofN⁶-benzoyladenine with adipic acid (1/0.5)

Abstract: The supramolecular architecture in a co-crystal of N(7)—H tautomeric form of N 6-benzoyladenine-adipic acid (1/0.5) is reported. The typical C=O⋯π and C—H⋯π interactions are also present in this structure.

Cited by 3 publications

References 26 publications

Crystal structure of a new molecular salt: 4-aminobenzenaminium 5-carboxypentanoate

Crystal structure of a new molecular salt: 4-aminobenzenaminium 5-carboxypentanoate

Design of two series of 1:1 cocrystals involving 4-amino-5-chloro-2,6-dimethylpyrimidine and carboxylic acids

Supramolecular hydrogen-bonding patterns in a 1:1 co-crystal of the N(7)—H tautomeric form ofN⁶-benzoyladenine with 4-hydroxybenzoic acid

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Supramolecular architecture in a co-crystal of the N(7)—H tautomeric form ofN6-benzoyladenine with adipic acid (1/0.5)

Abstract: The supra­molecular architecture in a co-crystal of N(7)—H tautomeric form of N 6-benzoyl­adenine-adipic acid (1/0.5) is reported. The typical C=O⋯π and C—H⋯π inter­actions are also present in this structure.

Cited by 3 publications

References 26 publications

Crystal structure of a new molecular salt: 4-aminobenzenaminium 5-carboxypentanoate

Crystal structure of a new molecular salt: 4-aminobenzenaminium 5-carboxypentanoate

Design of two series of 1:1 cocrystals involving 4-amino-5-chloro-2,6-dimethylpyrimidine and carboxylic acids

Supramolecular hydrogen-bonding patterns in a 1:1 co-crystal of the N(7)—H tautomeric form ofN6-benzoyladenine with 4-hydroxybenzoic acid

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Supramolecular architecture in a co-crystal of the N(7)—H tautomeric form ofN⁶-benzoyladenine with adipic acid (1/0.5)

Abstract: The supramolecular architecture in a co-crystal of N(7)—H tautomeric form of N 6-benzoyladenine-adipic acid (1/0.5) is reported. The typical C=O⋯π and C—H⋯π interactions are also present in this structure.

Supramolecular hydrogen-bonding patterns in a 1:1 co-crystal of the N(7)—H tautomeric form ofN⁶-benzoyladenine with 4-hydroxybenzoic acid