Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate: Dimeric structure formation via [O-H-O]- negative charge-assisted hydrogen bonds (-CAHB) with benzyltrimethylammonium counter-ions

Ravell Bengiat; Maayan Gil; Asne Klein; Benny Bogoslavsky; Shmuel Cohen; Joseph Almog

doi:10.1107/S2056989016002899

Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.0^3,14.0^4,12.0^6,11.0^18,26.0^19,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate: Dimeric structure formation via [O-H-O]^- negative charge-assisted hydrogen bonds (-CAHB) with benzyltrimethylammonium counter-ions

Ravell Bengiat, Maayan Gil, Asne Klein, Benny Bogoslavsky, Shmuel Cohen, Joseph Almog

Institute of Chemistry

The Hebrew University of Jerusalem

Research output: Contribution to journal › Article › peer-review

Abstract

The reaction between bis-ninhydrin resorcinol and benzyltrimethylammonium fluoride in ethanol has produced the title compound, 2C₁₀H₁₆N⁺·2C₂₄H₁₃O₈ ^-·1.5H2O, which contains a unique centrosymmetric supramolecular dimeric entity, where two deprotonated ligands are held together via two strong and short [O⋯O = 2.4395(13)Å] [O-H-O]^- bonds of the type negative charge-assisted hydrogen bonds (-CAHB). The central aromatic rings of the ligands create parallel-displaced π-π stacking at an interplanar distance of 3.381(1)Å, which helps stabilize the dimer. In the crystal, two symmetry-related solvent water molecules with a site occupancy of 0.75 are attached to the carbonyl groups of the dimer by weaker O-H⋯O hydrogen bonds, forming chains along [101].

Original language	English
Pages (from-to)	399-402
Number of pages	4
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	72
DOIs	https://doi.org/10.1107/S2056989016002899
State	Published - 2016

Keywords

crystal structure
negative charge-assisted hydrogen bond [(-)CAHB]
ninhydrin
supramolecular dimer
vasarene

All Science Journal Classification (ASJC) codes

General Chemistry
General Materials Science
Condensed Matter Physics

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10.1107/S2056989016002899

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Bengiat, R., Gil, M., Klein, A., Bogoslavsky, B., Cohen, S., & Almog, J. (2016). Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.0^3,14.0^4,12.0^6,11.0^18,26.0^19,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate: Dimeric structure formation via [O-H-O]^- negative charge-assisted hydrogen bonds (-CAHB) with benzyltrimethylammonium counter-ions. Acta Crystallographica Section E: Crystallographic Communications, 72, 399-402. https://doi.org/10.1107/S2056989016002899

Bengiat, Ravell ; Gil, Maayan ; Klein, Asne et al. / Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.0^3,14.0^4,12.0^6,11.0^18,26.0^19,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate : Dimeric structure formation via [O-H-O]^- negative charge-assisted hydrogen bonds (-CAHB) with benzyltrimethylammonium counter-ions. In: Acta Crystallographica Section E: Crystallographic Communications. 2016 ; Vol. 72. pp. 399-402.

@article{9252e7901afd4d4c84b8b1a7063b1760,

title = "Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate: Dimeric structure formation via [O-H-O]- negative charge-assisted hydrogen bonds (-CAHB) with benzyltrimethylammonium counter-ions",

abstract = "The reaction between bis-ninhydrin resorcinol and benzyltrimethylammonium fluoride in ethanol has produced the title compound, 2C10H16N+·2C24H13O8 -·1.5H2O, which contains a unique centrosymmetric supramolecular dimeric entity, where two deprotonated ligands are held together via two strong and short [O⋯O = 2.4395(13){\AA}] [O-H-O]- bonds of the type negative charge-assisted hydrogen bonds (-CAHB). The central aromatic rings of the ligands create parallel-displaced π-π stacking at an interplanar distance of 3.381(1){\AA}, which helps stabilize the dimer. In the crystal, two symmetry-related solvent water molecules with a site occupancy of 0.75 are attached to the carbonyl groups of the dimer by weaker O-H⋯O hydrogen bonds, forming chains along [101].",

keywords = "crystal structure, negative charge-assisted hydrogen bond [(-)CAHB], ninhydrin, supramolecular dimer, vasarene",

author = "Ravell Bengiat and Maayan Gil and Asne Klein and Benny Bogoslavsky and Shmuel Cohen and Joseph Almog",

note = "Publisher Copyright: {\textcopyright} 2016 Bengiat et al.s.",

year = "2016",

doi = "10.1107/S2056989016002899",

language = "الإنجليزيّة",

volume = "72",

pages = "399--402",

journal = "Acta Crystallographica Section E: Crystallographic Communications",

issn = "2056-9890",

publisher = "International Union of Crystallography",

}

Bengiat, R, Gil, M, Klein, A, Bogoslavsky, B, Cohen, S & Almog, J 2016, 'Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.0^3,14.0^4,12.0^6,11.0^18,26.0^19,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate: Dimeric structure formation via [O-H-O]^- negative charge-assisted hydrogen bonds (-CAHB) with benzyltrimethylammonium counter-ions', Acta Crystallographica Section E: Crystallographic Communications, vol. 72, pp. 399-402. https://doi.org/10.1107/S2056989016002899

Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.0^3,14.0^4,12.0^6,11.0^18,26.0^19,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate: Dimeric structure formation via [O-H-O]^- negative charge-assisted hydrogen bonds (-CAHB) with benzyltrimethylammonium counter-ions. / Bengiat, Ravell; Gil, Maayan; Klein, Asne et al.
In: Acta Crystallographica Section E: Crystallographic Communications, Vol. 72, 2016, p. 399-402.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate

T2 - Dimeric structure formation via [O-H-O]- negative charge-assisted hydrogen bonds (-CAHB) with benzyltrimethylammonium counter-ions

AU - Bengiat, Ravell

AU - Gil, Maayan

AU - Klein, Asne

AU - Bogoslavsky, Benny

AU - Cohen, Shmuel

AU - Almog, Joseph

PY - 2016

Y1 - 2016

N2 - The reaction between bis-ninhydrin resorcinol and benzyltrimethylammonium fluoride in ethanol has produced the title compound, 2C10H16N+·2C24H13O8 -·1.5H2O, which contains a unique centrosymmetric supramolecular dimeric entity, where two deprotonated ligands are held together via two strong and short [O⋯O = 2.4395(13)Å] [O-H-O]- bonds of the type negative charge-assisted hydrogen bonds (-CAHB). The central aromatic rings of the ligands create parallel-displaced π-π stacking at an interplanar distance of 3.381(1)Å, which helps stabilize the dimer. In the crystal, two symmetry-related solvent water molecules with a site occupancy of 0.75 are attached to the carbonyl groups of the dimer by weaker O-H⋯O hydrogen bonds, forming chains along [101].

AB - The reaction between bis-ninhydrin resorcinol and benzyltrimethylammonium fluoride in ethanol has produced the title compound, 2C10H16N+·2C24H13O8 -·1.5H2O, which contains a unique centrosymmetric supramolecular dimeric entity, where two deprotonated ligands are held together via two strong and short [O⋯O = 2.4395(13)Å] [O-H-O]- bonds of the type negative charge-assisted hydrogen bonds (-CAHB). The central aromatic rings of the ligands create parallel-displaced π-π stacking at an interplanar distance of 3.381(1)Å, which helps stabilize the dimer. In the crystal, two symmetry-related solvent water molecules with a site occupancy of 0.75 are attached to the carbonyl groups of the dimer by weaker O-H⋯O hydrogen bonds, forming chains along [101].

KW - crystal structure

KW - negative charge-assisted hydrogen bond [(-)CAHB]

KW - ninhydrin

KW - supramolecular dimer

KW - vasarene

UR - http://www.scopus.com/inward/record.url?scp=84960155660&partnerID=8YFLogxK

U2 - 10.1107/S2056989016002899

DO - 10.1107/S2056989016002899

M3 - مقالة

SN - 2056-9890

VL - 72

SP - 399

EP - 402

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

ER -