N—H...O and O—H...O hydrogen bonds in crystal engineering: trimethoprim hydrogen glutarate

Robert, Jebamony Justin; Raj, S. Baskar; Muthiah, Packianathan Thomas

doi:10.1107/s1600536801018001

Cited by 29 publications

(48 citation statements)

References 10 publications

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“…6). This type of motif has been reported in the crystal structures of trimethoprim hydrogen glutarate (Robert et al, 2001), trimethoprim formate (Umadevi et al, 2002) and pyrimethamine 3,5-dinitrobenzoate (Subashini et al, 2007). The 2-amino group at N2 forms a bifurcated hydrogen bond (Table 3) with carboxyl atom O1 ii and atom N6 ii of a 3-hydroxypicolinate anion [graph-set R 2 1 (5)].…”

Section: Figuresupporting

confidence: 54%

Charge-assisted hydrogen-bonded supramolecular networks in acetoguanaminium hydrogen phthalate, acetoguanaminium hydrogen maleate and acetoguanaminium 3-hydroxypicolinate monohydrate

et al. 2010

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In 2,4-diamino-6-methyl-1,3,5-triazin-1-ium (acetoguanaminium) hydrogen phthalate, C(4)H(8)N(5)(+) x C(8)H(5)O(4)(-), (I), acetoguanaminium hydrogen maleate, C(4)H(8)N(5)(+) x C(4)H(3)O(4)(-), (II), and acetoguanaminium 3-hydroxypicolinate monohydrate, C(4)H(8)N(5)(+) x C(6)H(4)NO(3)(-) x H(2)O, (III), the acetoguanaminium cations interact with the carboxylate groups of the corresponding anions via a pair of nearly parallel N-H...O hydrogen bonds, forming R(2)(2)(8) ring motifs. In (II) and (III), N-H...N base-pairing is observed, while there is none in (I). In (II), a series of fused R(3)(2)(8), R(2)(2)(8) and R(3)(2)(8) hydrogen-bonded rings plus fused R(2)(2)(8), R(6)(2)(12) and R(2)(2)(8) ring motifs occur alternately, aggregating into a supramolecular ladder-like arrangement. In (III), R(2)(2)(8) motifs occur on either side of a further ring formed by pairs of N-H...O hydrogen bonds, forming an array of three fused hydrogen-bonded rings. In (I) and (II), the anions form a typical intramolecular O-H...O hydrogen bond with graph set S(7), whereas in (III) an intramolecular hydrogen bond with graph set S(6) is formed.

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Section: Figuresupporting

confidence: 54%

Charge-assisted hydrogen-bonded supramolecular networks in acetoguanaminium hydrogen phthalate, acetoguanaminium hydrogen maleate and acetoguanaminium 3-hydroxypicolinate monohydrate

et al. 2010

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“…R 2 2 (8), R 2 4 (8) and R 2 2 (8). This type of DDAA array has also been observed in some TMP salts (Robert et al, 2001;Umadevi et al, 2002;Raj et al, 2003;Subashini et al, 2007;Thanigaimani et al, 2007). The DDAA array involves two TMP cations and two DTPC anions, generating a four-molecule aggregate.…”

Section: Compoundmentioning

confidence: 56%

Supramolecular hydrogen-bonding patterns in salts of the antifolate drugs trimethoprim and pyrimethamine

Darious

Muthiah

Perdih

2018

Acta Crystallogr C Struct Chem

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Nine salts of the antifolate drugs trimethoprim and pyrimethamine, namely, trimethoprimium [or 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium] 2,5-dichlorothiophene-3-carboxylate monohydrate (TMPDCTPC, 1:1), CHNO·CHClOS, (I), trimethoprimium 3-bromothiophene-2-carboxylate monohydrate, (TMPBTPC, 1:1:1), CHNO·CHBrOS·HO, (II), trimethoprimium 3-chlorothiophene-2-carboxylate monohydrate (TMPCTPC, 1:1:1), CHNO·CHClOS·HO, (III), trimethoprimium 5-methylthiophene-2-carboxylate monohydrate (TMPMTPC, 1:1:1), CHNO·CHOS·HO, (IV), trimethoprimium anthracene-9-carboxylate sesquihydrate (TMPAC, 2:2:3), CHNO·CHO·1.5HO, (V), pyrimethaminium [or 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium] 2,5-dichlorothiophene-3-carboxylate (PMNDCTPC, 1:1), CHClN·CHClOS, (VI), pyrimethaminium 5-bromothiophene-2-carboxylate (PMNBTPC, 1:1), CHClN·CHBrOS, (VII), pyrimethaminium anthracene-9-carboxylate ethanol monosolvate monohydrate (PMNAC, 1:1:1:1), CHClN·CHO·CHOH·HO, (VIII), and bis(pyrimethaminium) naphthalene-1,5-disulfonate (PMNNSA, 2:1), 2CHClN·CHOS, (IX), have been prepared and characterized by single-crystal X-ray diffraction. In all the crystal structures, the pyrimidine N1 atom is protonated. In salts (I)-(III) and (VI)-(IX), the 2-aminopyrimidinium cation interacts with the corresponding anion via a pair of N-H...O hydrogen bonds, generating the robust R(8) supramolecular heterosynthon. In salt (IV), instead of forming the R(8) heterosynthon, the carboxylate group bridges two pyrimidinium cations via N-H...O hydrogen bonds. In salt (V), one of the carboxylate O atoms bridges the N1-H group and a 2-amino H atom of the pyrimidinium cation to form a smaller R(6) ring instead of the R(8) ring. In salt (IX), the sulfonate O atoms mimic the role of carboxylate O atoms in forming an R(8) ring motif. In salts (II)-(IX), the pyrimidinium cation forms base pairs via a pair of N-H...N hydrogen bonds, generating a ring motif [R(8) homosynthon]. Compounds (II) and (III) are isomorphous. The quadruple DDAA (D = hydrogen-bond donor and A = hydrogen-bond acceptor) array is observed in (I). In salts (II)-(IV) and (VI)-(IX), quadruple DADA arrays are present. In salts (VI) and (VII), both DADA and DDAA arrays co-exist. The crystal structures are further stabilized by π-π stacking interactions [in (I), (V) and (VII)-(IX)], C-H...π interactions [in (IV)-(V) and (VII)-(IX)], C-Br...π interactions [in (II)] and C-Cl...π interactions [in (I), (III) and (VI)]. Cl...O and Cl...Cl halogen-bond interactions are present in (I) and (VI), with distances and angles of 3.0020 (18) and 3.5159 (16) Å, and 165.56 (10) and 154.81 (11)°, respectively.

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“…4. Similar types of carboxylcarboxylate interactions have also been observed in the crystal structures, trimethoprim-hydrogen glutarate [21] and trimethoprim-terephthalate terephthalic acid [22]. In both the compounds, p-p stacking is observed between the 2-amino-4,6-dimethylpyrimidine (molecule A and molecule B) with perpendicular separation of 3.357 Å (1), 3.264Å (2), a centroid-to-centroid distance of 3.441(3) Å (1), 3.638(2) Å (2) and slip angle ( the angle between the centroid vector normal to the plane) of 15.37°(1) and 22.03° (2).…”

mentioning

confidence: 52%

The interplay of hydrogen-bonding and metal-coordination motifs in the formation of supramolecular patterns: Copper/zinc malonates–aminopyrimidine complexes

Hemamalini¹,

Muthiah²,

Butcher³

et al. 2006

Inorganic Chemistry Communications

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N—H...O and O—H...O hydrogen bonds in crystal engineering: trimethoprim hydrogen glutarate

Cited by 29 publications

References 10 publications

Charge-assisted hydrogen-bonded supramolecular networks in acetoguanaminium hydrogen phthalate, acetoguanaminium hydrogen maleate and acetoguanaminium 3-hydroxypicolinate monohydrate

Charge-assisted hydrogen-bonded supramolecular networks in acetoguanaminium hydrogen phthalate, acetoguanaminium hydrogen maleate and acetoguanaminium 3-hydroxypicolinate monohydrate

Supramolecular hydrogen-bonding patterns in salts of the antifolate drugs trimethoprim and pyrimethamine

The interplay of hydrogen-bonding and metal-coordination motifs in the formation of supramolecular patterns: Copper/zinc malonates–aminopyrimidine complexes

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