Structural study of mefloquinium salts with three isomeric n-nitrobenzoates (n=2, 3, and 4)

Jan Skakle, Solange M. S. V. Wardell, James Lewis Wardell, Edward R. T. Tiekink

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The crystal and molecular structures of three racemic erythro-(R*, S*)-(+/-)-alpha-2-piperidiny1-2,8-bis(trifluoromethyl)-4-quinolinemethanol n-nitrobenzoates, n = 2, 3, and 4, are described. The cations uniformly adopt an L-shaped geometry with protonation leading to a piperidin-1-ium ring in each case. A non-planar arrangement is found for the anion in (1; n = 2), owing to steric congestion, but almost planar arrangements are found in each of the anions in (2; n = 3) and (3; n = 4). Supramolecular chains are found in each of the crystal structures but these are sustained by different hydrogen bonding synthons. More efficient crystal packing in (3; n = 4) is correlated with a single synthon as opposed to two distinct synthons in each of (1; n = 2) and (2; n = 3). Crystal data for (1; n = 2): monoclinic, P2(1)/n, a = 13.2144(6), b = 8.1028(2), c = 22.9724(9) angstrom, beta = 105.919(1)degrees, V = 2365.41(15) angstrom(3), Z = 4, R = 0.053. Crystal data for (2; n = 3): monoclinic, P2(1)/n, a = 6.8389(2), b = 12.8432(4), c = 26.7910(9) angstrom, beta = 90.868(2)degrees, V = 2352.87(13) angstrom(3), Z = 4, R = 0.044. Crystal data for (3; n = 4): monoclinic, P2(1)/n, a = 16.9854(8), b = 6.5069(2), c = 20.2083(9) angstrom, beta = 92.116(2)degrees, V = 2231.94(16) angstrom(3), = 4, R = 0.065.

Original languageEnglish
Pages (from-to)68-77
Number of pages10
JournalZeitschrift für Kristallographie
Volume226
Issue number1
DOIs
Publication statusPublished - Jan 2011

Keywords

  • mefloquine
  • organic salt
  • conformation
  • hydrogen bonding
  • x-ray diffraction
  • single crystal structure analysis
  • crystal-structure
  • hydrochloride
  • fluorine
  • malaria
  • drug

Cite this

Structural study of mefloquinium salts with three isomeric n-nitrobenzoates (n=2, 3, and 4). / Skakle, Jan; Wardell, Solange M. S. V.; Wardell, James Lewis; Tiekink, Edward R. T.

In: Zeitschrift für Kristallographie, Vol. 226, No. 1, 01.2011, p. 68-77.

Research output: Contribution to journalArticle

Skakle, Jan ; Wardell, Solange M. S. V. ; Wardell, James Lewis ; Tiekink, Edward R. T. / Structural study of mefloquinium salts with three isomeric n-nitrobenzoates (n=2, 3, and 4). In: Zeitschrift für Kristallographie. 2011 ; Vol. 226, No. 1. pp. 68-77.
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title = "Structural study of mefloquinium salts with three isomeric n-nitrobenzoates (n=2, 3, and 4)",
abstract = "The crystal and molecular structures of three racemic erythro-(R*, S*)-(+/-)-alpha-2-piperidiny1-2,8-bis(trifluoromethyl)-4-quinolinemethanol n-nitrobenzoates, n = 2, 3, and 4, are described. The cations uniformly adopt an L-shaped geometry with protonation leading to a piperidin-1-ium ring in each case. A non-planar arrangement is found for the anion in (1; n = 2), owing to steric congestion, but almost planar arrangements are found in each of the anions in (2; n = 3) and (3; n = 4). Supramolecular chains are found in each of the crystal structures but these are sustained by different hydrogen bonding synthons. More efficient crystal packing in (3; n = 4) is correlated with a single synthon as opposed to two distinct synthons in each of (1; n = 2) and (2; n = 3). Crystal data for (1; n = 2): monoclinic, P2(1)/n, a = 13.2144(6), b = 8.1028(2), c = 22.9724(9) angstrom, beta = 105.919(1)degrees, V = 2365.41(15) angstrom(3), Z = 4, R = 0.053. Crystal data for (2; n = 3): monoclinic, P2(1)/n, a = 6.8389(2), b = 12.8432(4), c = 26.7910(9) angstrom, beta = 90.868(2)degrees, V = 2352.87(13) angstrom(3), Z = 4, R = 0.044. Crystal data for (3; n = 4): monoclinic, P2(1)/n, a = 16.9854(8), b = 6.5069(2), c = 20.2083(9) angstrom, beta = 92.116(2)degrees, V = 2231.94(16) angstrom(3), = 4, R = 0.065.",
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T1 - Structural study of mefloquinium salts with three isomeric n-nitrobenzoates (n=2, 3, and 4)

AU - Skakle, Jan

AU - Wardell, Solange M. S. V.

AU - Wardell, James Lewis

AU - Tiekink, Edward R. T.

PY - 2011/1

Y1 - 2011/1

N2 - The crystal and molecular structures of three racemic erythro-(R*, S*)-(+/-)-alpha-2-piperidiny1-2,8-bis(trifluoromethyl)-4-quinolinemethanol n-nitrobenzoates, n = 2, 3, and 4, are described. The cations uniformly adopt an L-shaped geometry with protonation leading to a piperidin-1-ium ring in each case. A non-planar arrangement is found for the anion in (1; n = 2), owing to steric congestion, but almost planar arrangements are found in each of the anions in (2; n = 3) and (3; n = 4). Supramolecular chains are found in each of the crystal structures but these are sustained by different hydrogen bonding synthons. More efficient crystal packing in (3; n = 4) is correlated with a single synthon as opposed to two distinct synthons in each of (1; n = 2) and (2; n = 3). Crystal data for (1; n = 2): monoclinic, P2(1)/n, a = 13.2144(6), b = 8.1028(2), c = 22.9724(9) angstrom, beta = 105.919(1)degrees, V = 2365.41(15) angstrom(3), Z = 4, R = 0.053. Crystal data for (2; n = 3): monoclinic, P2(1)/n, a = 6.8389(2), b = 12.8432(4), c = 26.7910(9) angstrom, beta = 90.868(2)degrees, V = 2352.87(13) angstrom(3), Z = 4, R = 0.044. Crystal data for (3; n = 4): monoclinic, P2(1)/n, a = 16.9854(8), b = 6.5069(2), c = 20.2083(9) angstrom, beta = 92.116(2)degrees, V = 2231.94(16) angstrom(3), = 4, R = 0.065.

AB - The crystal and molecular structures of three racemic erythro-(R*, S*)-(+/-)-alpha-2-piperidiny1-2,8-bis(trifluoromethyl)-4-quinolinemethanol n-nitrobenzoates, n = 2, 3, and 4, are described. The cations uniformly adopt an L-shaped geometry with protonation leading to a piperidin-1-ium ring in each case. A non-planar arrangement is found for the anion in (1; n = 2), owing to steric congestion, but almost planar arrangements are found in each of the anions in (2; n = 3) and (3; n = 4). Supramolecular chains are found in each of the crystal structures but these are sustained by different hydrogen bonding synthons. More efficient crystal packing in (3; n = 4) is correlated with a single synthon as opposed to two distinct synthons in each of (1; n = 2) and (2; n = 3). Crystal data for (1; n = 2): monoclinic, P2(1)/n, a = 13.2144(6), b = 8.1028(2), c = 22.9724(9) angstrom, beta = 105.919(1)degrees, V = 2365.41(15) angstrom(3), Z = 4, R = 0.053. Crystal data for (2; n = 3): monoclinic, P2(1)/n, a = 6.8389(2), b = 12.8432(4), c = 26.7910(9) angstrom, beta = 90.868(2)degrees, V = 2352.87(13) angstrom(3), Z = 4, R = 0.044. Crystal data for (3; n = 4): monoclinic, P2(1)/n, a = 16.9854(8), b = 6.5069(2), c = 20.2083(9) angstrom, beta = 92.116(2)degrees, V = 2231.94(16) angstrom(3), = 4, R = 0.065.

KW - mefloquine

KW - organic salt

KW - conformation

KW - hydrogen bonding

KW - x-ray diffraction

KW - single crystal structure analysis

KW - crystal-structure

KW - hydrochloride

KW - fluorine

KW - malaria

KW - drug

U2 - 10.1524/zkri.2011.1280

DO - 10.1524/zkri.2011.1280

M3 - Article

VL - 226

SP - 68

EP - 77

JO - Zeitschrift für Kristallographie

JF - Zeitschrift für Kristallographie

SN - 0044-2968

IS - 1

ER -