2-Aminopyrimidine–succinic acid (1/1) cocrystal

Etter, Margaret C.; Adsmond, Daniel A.; Britton, Doyle

doi:10.1107/s010827018901365x

Cited by 115 publications

(139 citation statements)

References 4 publications

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“…The bond distances and angles of 2-fiminopyrimidine in all four complexes are similar to those found in other complexes (O'Reilly, Smith & Kennard, 1984;Kennard, Stewart, O'Reilly, Smith & White, 1985;Etter, Adsmond & Britton, 1990;Zanchini & Willett, 1990) and for the free ligand (Scheinbeim & Schempp, 1976;Furberg, Grogaard & Smedsrud, 1979).…”

Section: Commentsupporting

confidence: 60%

Di-μ-sulfato-O:O'-bis[(2-aminopyrimidine-N1)triaquacobalt(II)] Dihydrate (1), catena-Poly[bis(2-aminopyrimidine-N1)diaquanickel(II)-μ-sulfato-O:O' 2-Aminopyrimidine] (2), (2-Aminopyrimidine-N1)pentaaquanickel(II) Sulfate 2-Aminopyrimidine (3) and catena-Poly[bis(2-aminopyrimidine-N1)aquacopper(ii)-μ-sulfato-O:O' Dihydrate] (4)

Lumme¹,

Knuuttila²,

Lindell³

1996

Acta Crystallogr C

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Section: Commentsupporting

confidence: 60%

Di-μ-sulfato-O:O'-bis[(2-aminopyrimidine-N1)triaquacobalt(II)] Dihydrate (1), catena-Poly[bis(2-aminopyrimidine-N1)diaquanickel(II)-μ-sulfato-O:O' 2-Aminopyrimidine] (2), (2-Aminopyrimidine-N1)pentaaquanickel(II) Sulfate 2-Aminopyrimidine (3) and catena-Poly[bis(2-aminopyrimidine-N1)aquacopper(ii)-μ-sulfato-O:O' Dihydrate] (4)

Lumme¹,

Knuuttila²,

Lindell³

1996

Acta Crystallogr C

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“…These include a centrosymmetric ring, closed by N--H...O hydrogen bonds, R~(8) according to graph-set notation (Etter, MacDonald & Bernstein, 1990), and an infinite chain also made by the N--H.…”

Section: Dc(5)r~(5)mentioning

confidence: 99%

“…Our approach is generally based on the method described by Etter and coworkers (Etter, 1990;Etter, MacDonald & Bernstein, 1990;Bernstein, Etter & MacDonald 1990;Bernstein, 1991). We introduced a graph-set analysis to explore its ability to identify a characteristic molecular interaction pattern that might predict interactions with vastly different partners, including enzyme active sites, molecular surfaces and receptor binding sites.…”

Section: Graph-set Analysismentioning

confidence: 99%

Hydrogen-bond patterns in 1,4-dihydro-2,3-quinoxalinediones: ligands for the glycine modulatory site on the NMDA receptor

Kubicki¹,

Kindopp²,

Capparelli³

et al. 1996

Acta Crystallogr Sect B

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The crystal structures of five 1,4-dihydro-2,3-quinoxalinediones, antagonists of the NMDA modulatory glycine binding site on the excitary amino acid (EAA) receptor complex, have been determined: (I) 6,7-dinitro-l,4-dihydro-2,3-quinoxalinedione (DNQX); (II) 5,7-dinitro-1,4-dihydro-2,3-quinoxalinedione (MNQX); (III) 6-nitro-1,4-dihydro-2,3-quinoxalinedione hydrate; (IV) 6,7-dichloro-l,4-dihydro-2,3-quinoxalinedione; (V) 5,7-dichloro-1,4-dihydro-2,3-quinoxalinedione dimethylformamide. The crystal structure of the most active compound (II) contains a unique intramolecular N--H...O(NO2) hydrogen bond, which may be important for activity, as semiempirical calculations show that this bond is stable over a wide range of dihedral angles between the planes of the molecule and of the nitro group. In the other compounds the intermolecular hydrogen bonds connect molecules into three-dimensional networks. In compounds (I), (III) and (IV) headto-tail :r-stacking is found between molecules connected by a center of symmetry. The geometries of the hydrogen-bonded --NH--C--O fragments show evidence of zr-cooperativity or resonance-assisted hydrogen bonding. Graph-set analysis of the hydrogenbond patterns of quinoxalinedione derivatives shows a tendency to form two types of hydrogen-bonding motifs: a centrosymmetric dimeric ring and an infinite chain. Even though this pattern may be modified by the presence of additional hydrogen-bond acceptors and/or donors, as well as by solvent molecules, general similarities have been found. Comparison of all quinoxalinedione structures suggests that the hydrogen-bonding pattern necessary for the biological activity at the glycine binding site contains one donor and two acceptors.

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“…Hydrogen bonds often provide the strongest intermolecular forces between molecules in organic molecular crystals and hence often dictate the preferred packing arrangement. The general principles underlying hydrogenbond formation are reasonably well understood and the structures of hydrogen-bonded crystals can often be rationalized in terms of preferred combinations of hydrogen-bond donors and acceptors (Etter, 1990;Etter, MacDonald & Bemstein, 1990;Etter & Reutzel, 1991). Herein we describe the extensive C--H...I-interactions in two cationic ferrocene derivatives.…”

mentioning

confidence: 99%