Novel, predicted patterns of supramolecular self-assembly, afforded by tetrameric R44(12) rings of C2 symmetry in the crystal structures of 2-hydroxy-1-cyclopentanecarboxylic acid, 2-hydroxy-1-cyclohexanecarboxylic acid and 2-hydroxy-1-cycloheptanecarboxylic acid

A. Kálmán, László Fábián, G. Argay, G. Bernáth, Zsuzsanna Gyarmati

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Abstract

Determination of the crystal structures of the homologous (1R*,2R*)-trans-2-hydroxy-1-cyclopentanecarboxylic acid (5T), (1R*,2S*)-cis-2-hydroxy-1-cyclohexanecarboxylic acid (6C) and (1R*,2S*)-cis-2-hydroxy-1-cycloheptanecarboxylic acid (7C) proved a predicted pattern of supramolecular close packing. The prediction was based on the common features observed in the crystal structures of six related 2-hydroxy-1-cyclopentanecarboxylic acids and analogous carboxamides [Kálmán et al. (2001). Acta Cryst. B57, 539-550]. This pattern is characterized by tetrameric R44(12) rings of C2 symmetry formed from dimeric R22(12) rings. The C2 symmetry of such tetramers is not common in the literature, usually they have Ci symmetry. Both types of tetramers are formed from dimers with similar or opposite orientation. The R22(12) dimers differ in their hydrogen bonds. In 5T the monomers are joined by a pair of O1-H⋯-O2=C bonds, whereas in 7C they are joined by a pair of O3-H⋯O1-H bonds. In 6C 60% of the disordered R22(12) dimers are similar to those in 7C, while 40% resemble those in 5T. Apart from these hydrogen-bonding differences and the ring-size differences, the three crystals exhibit isostructurality.

Original languageEnglish
Pages (from-to)494-501
Number of pages8
JournalActa Crystallographica Section B
Volume58
Issue number3 PART 2
DOIs
Publication statusPublished - Jun 2002

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Hydroxy Acids
Crystal symmetry
Dimers
Self assembly
self assembly
Crystal structure
acids
crystal structure
Acids
rings
dimers
Hydrogen bonds
symmetry
Hydrogen Bonding
Hydrogen
Monomers
Crystals
monomers
hydrogen bonds
cyclohexanecarboxylic acid

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Structural Biology

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title = "Novel, predicted patterns of supramolecular self-assembly, afforded by tetrameric R44(12) rings of C2 symmetry in the crystal structures of 2-hydroxy-1-cyclopentanecarboxylic acid, 2-hydroxy-1-cyclohexanecarboxylic acid and 2-hydroxy-1-cycloheptanecarboxylic acid",
abstract = "Determination of the crystal structures of the homologous (1R*,2R*)-trans-2-hydroxy-1-cyclopentanecarboxylic acid (5T), (1R*,2S*)-cis-2-hydroxy-1-cyclohexanecarboxylic acid (6C) and (1R*,2S*)-cis-2-hydroxy-1-cycloheptanecarboxylic acid (7C) proved a predicted pattern of supramolecular close packing. The prediction was based on the common features observed in the crystal structures of six related 2-hydroxy-1-cyclopentanecarboxylic acids and analogous carboxamides [K{\'a}lm{\'a}n et al. (2001). Acta Cryst. B57, 539-550]. This pattern is characterized by tetrameric R44(12) rings of C2 symmetry formed from dimeric R22(12) rings. The C2 symmetry of such tetramers is not common in the literature, usually they have Ci symmetry. Both types of tetramers are formed from dimers with similar or opposite orientation. The R22(12) dimers differ in their hydrogen bonds. In 5T the monomers are joined by a pair of O1-H⋯-O2=C bonds, whereas in 7C they are joined by a pair of O3-H⋯O1-H bonds. In 6C 60{\%} of the disordered R22(12) dimers are similar to those in 7C, while 40{\%} resemble those in 5T. Apart from these hydrogen-bonding differences and the ring-size differences, the three crystals exhibit isostructurality.",
author = "A. K{\'a}lm{\'a}n and L{\'a}szl{\'o} F{\'a}bi{\'a}n and G. Argay and G. Bern{\'a}th and Zsuzsanna Gyarmati",
year = "2002",
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language = "English",
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T1 - Novel, predicted patterns of supramolecular self-assembly, afforded by tetrameric R44(12) rings of C2 symmetry in the crystal structures of 2-hydroxy-1-cyclopentanecarboxylic acid, 2-hydroxy-1-cyclohexanecarboxylic acid and 2-hydroxy-1-cycloheptanecarboxylic acid

AU - Kálmán, A.

AU - Fábián, László

AU - Argay, G.

AU - Bernáth, G.

AU - Gyarmati, Zsuzsanna

PY - 2002/6

Y1 - 2002/6

N2 - Determination of the crystal structures of the homologous (1R*,2R*)-trans-2-hydroxy-1-cyclopentanecarboxylic acid (5T), (1R*,2S*)-cis-2-hydroxy-1-cyclohexanecarboxylic acid (6C) and (1R*,2S*)-cis-2-hydroxy-1-cycloheptanecarboxylic acid (7C) proved a predicted pattern of supramolecular close packing. The prediction was based on the common features observed in the crystal structures of six related 2-hydroxy-1-cyclopentanecarboxylic acids and analogous carboxamides [Kálmán et al. (2001). Acta Cryst. B57, 539-550]. This pattern is characterized by tetrameric R44(12) rings of C2 symmetry formed from dimeric R22(12) rings. The C2 symmetry of such tetramers is not common in the literature, usually they have Ci symmetry. Both types of tetramers are formed from dimers with similar or opposite orientation. The R22(12) dimers differ in their hydrogen bonds. In 5T the monomers are joined by a pair of O1-H⋯-O2=C bonds, whereas in 7C they are joined by a pair of O3-H⋯O1-H bonds. In 6C 60% of the disordered R22(12) dimers are similar to those in 7C, while 40% resemble those in 5T. Apart from these hydrogen-bonding differences and the ring-size differences, the three crystals exhibit isostructurality.

AB - Determination of the crystal structures of the homologous (1R*,2R*)-trans-2-hydroxy-1-cyclopentanecarboxylic acid (5T), (1R*,2S*)-cis-2-hydroxy-1-cyclohexanecarboxylic acid (6C) and (1R*,2S*)-cis-2-hydroxy-1-cycloheptanecarboxylic acid (7C) proved a predicted pattern of supramolecular close packing. The prediction was based on the common features observed in the crystal structures of six related 2-hydroxy-1-cyclopentanecarboxylic acids and analogous carboxamides [Kálmán et al. (2001). Acta Cryst. B57, 539-550]. This pattern is characterized by tetrameric R44(12) rings of C2 symmetry formed from dimeric R22(12) rings. The C2 symmetry of such tetramers is not common in the literature, usually they have Ci symmetry. Both types of tetramers are formed from dimers with similar or opposite orientation. The R22(12) dimers differ in their hydrogen bonds. In 5T the monomers are joined by a pair of O1-H⋯-O2=C bonds, whereas in 7C they are joined by a pair of O3-H⋯O1-H bonds. In 6C 60% of the disordered R22(12) dimers are similar to those in 7C, while 40% resemble those in 5T. Apart from these hydrogen-bonding differences and the ring-size differences, the three crystals exhibit isostructurality.

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JO - Acta Crystallographica Section B: Structural Science

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