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Molecular structure studies of (1S,2S)-2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol.

Zhang T, Paluch K, Scalabrino G, Frankish N, Healy AM, Sheridan H - J Mol Struct (2015)

Bottom Line: The single enantiomer (1S,2S)-2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol (2), has recently been synthesized and isolated from its corresponding diastereoisomer (1).The molecular and crystal structures of this novel compound have been fully analyzed.The relative and absolute configurations have been determined by using a combination of analytical tools including X-ray crystallography, X-ray Powder Diffraction (XRPD) analysis and Nuclear Magnetic Resonance (NMR) spectroscopy.

View Article: PubMed Central - PubMed

Affiliation: Trino Therapeutics Ltd, The Tower, Trinity Technology and Enterprise Campus, Dublin 2, Ireland ; Novel Drug Discovery Group, School of Pharmacy and Pharmaceutical Sciences & Trinity Biomedical Sciences Institute, Trinity College, Dublin 2, Ireland.

ABSTRACT

The single enantiomer (1S,2S)-2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol (2), has recently been synthesized and isolated from its corresponding diastereoisomer (1). The molecular and crystal structures of this novel compound have been fully analyzed. The relative and absolute configurations have been determined by using a combination of analytical tools including X-ray crystallography, X-ray Powder Diffraction (XRPD) analysis and Nuclear Magnetic Resonance (NMR) spectroscopy.

No MeSH data available.


Fingerprint plots and corresponding Hirshfeld surface coverage of compound (4).
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f0015: Fingerprint plots and corresponding Hirshfeld surface coverage of compound (4).

Mentions: All short-range contacts in Table 1 were depicted in Hirshfeld surface (HS) analysis [18] as a red hotspots (Fig. 2) corresponding to dnorm reciprocal interactions [19–21]. Red1 hot spots indicate interactions stronger than Van der Waals interactions such as hydrogen bonds and/or weaker short-range contacts. HS analysis allows to calculate a percentage of involvement of inter- and intra-molecular atoms reciprocal interactions into overall coverage of HS which is generated on boundary of intermolecular interactions. HS may be converted to two-dimensional presentation of interactions called fingerprint plot (Fig. 3) [22]. C15–Br01 and C14–Br01 short-range contact corresponds only to 4.4% of overall HS and covers shorter de/di distance interactions from 1.6–1.8 Å up to 2.2–2.2 Å [23]. Even weaker than short-range interactions were depicted between hydrogens and bromine or oxygen atoms of carbonyl group, though they covered larger HS area. Respectively H–Br and H–O interactions covered 7.7% and 6.0% of HS. The largest input in HS coverage have inter- and intra-molecular interactions between hydrogens itself and hydrogens and carbons of compound (4). Respectively H–C and H–H interactions cover 31.4% and 49.7% of HS in Fig. 3. Apart they cover the largest HS area, taking into account that the shorter is distance between interacting atoms the stronger is its reciprocal interaction, H–C and H–H interactions form the strongest short range contacts respectively between C4–H9b and H6a–H9b both related to indene moiety of compound (4) structure.


Molecular structure studies of (1S,2S)-2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol.

Zhang T, Paluch K, Scalabrino G, Frankish N, Healy AM, Sheridan H - J Mol Struct (2015)

Fingerprint plots and corresponding Hirshfeld surface coverage of compound (4).
© Copyright Policy - CC BY
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4308634&req=5

f0015: Fingerprint plots and corresponding Hirshfeld surface coverage of compound (4).
Mentions: All short-range contacts in Table 1 were depicted in Hirshfeld surface (HS) analysis [18] as a red hotspots (Fig. 2) corresponding to dnorm reciprocal interactions [19–21]. Red1 hot spots indicate interactions stronger than Van der Waals interactions such as hydrogen bonds and/or weaker short-range contacts. HS analysis allows to calculate a percentage of involvement of inter- and intra-molecular atoms reciprocal interactions into overall coverage of HS which is generated on boundary of intermolecular interactions. HS may be converted to two-dimensional presentation of interactions called fingerprint plot (Fig. 3) [22]. C15–Br01 and C14–Br01 short-range contact corresponds only to 4.4% of overall HS and covers shorter de/di distance interactions from 1.6–1.8 Å up to 2.2–2.2 Å [23]. Even weaker than short-range interactions were depicted between hydrogens and bromine or oxygen atoms of carbonyl group, though they covered larger HS area. Respectively H–Br and H–O interactions covered 7.7% and 6.0% of HS. The largest input in HS coverage have inter- and intra-molecular interactions between hydrogens itself and hydrogens and carbons of compound (4). Respectively H–C and H–H interactions cover 31.4% and 49.7% of HS in Fig. 3. Apart they cover the largest HS area, taking into account that the shorter is distance between interacting atoms the stronger is its reciprocal interaction, H–C and H–H interactions form the strongest short range contacts respectively between C4–H9b and H6a–H9b both related to indene moiety of compound (4) structure.

Bottom Line: The single enantiomer (1S,2S)-2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol (2), has recently been synthesized and isolated from its corresponding diastereoisomer (1).The molecular and crystal structures of this novel compound have been fully analyzed.The relative and absolute configurations have been determined by using a combination of analytical tools including X-ray crystallography, X-ray Powder Diffraction (XRPD) analysis and Nuclear Magnetic Resonance (NMR) spectroscopy.

View Article: PubMed Central - PubMed

Affiliation: Trino Therapeutics Ltd, The Tower, Trinity Technology and Enterprise Campus, Dublin 2, Ireland ; Novel Drug Discovery Group, School of Pharmacy and Pharmaceutical Sciences & Trinity Biomedical Sciences Institute, Trinity College, Dublin 2, Ireland.

ABSTRACT

The single enantiomer (1S,2S)-2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol (2), has recently been synthesized and isolated from its corresponding diastereoisomer (1). The molecular and crystal structures of this novel compound have been fully analyzed. The relative and absolute configurations have been determined by using a combination of analytical tools including X-ray crystallography, X-ray Powder Diffraction (XRPD) analysis and Nuclear Magnetic Resonance (NMR) spectroscopy.

No MeSH data available.