title: (1S)-1-Phenylethanaminium 4-{[(1S,2S)-1-hydroxy-2,3-dihydro-1H,1'H-[2,2'-biinden]-2-yl]methyl}benzoate.
abstract: The title molecular salt, C(8)H(12)N(+)·C(26)H(21)O(3)(-), contains a dimeric indane pharmacophore that demonstrates potent anti-inflammatory activity. The indane group of the anion exhibits some disorder about the α-C atom, which appears common to many structures containing this group. A model to account for the slight disorder was attempted, but this was deemed unsuccessful because applying bond-length constraints to all the bonds about the α-C atom led to instability in the refinement. The absolute configuration was determined crystallographically as S,S,S by anomalous dispersion methods with reference to both the Flack parameter and Bayesian statistics on Bijvoet differences. The configuration was also determined by an a priori knowledge of the absolute configuration of the (1S)-1-phenylethanaminium counter-ion. The molecules pack in the crystal structure to form an infinite two-dimensional hydrogen-bond network in the (100) plane of the unit cell.
authors.affiliation: Pharmorphix Solid State Services, A Sigma-Aldrich Company, Cambridge, England, UK. chris.frampton@sial.com
authors.forename: Christopher S
authors.initials: CS
authors.lastname: Frampton
authors.forename: Tao
authors.initials: T
authors.lastname: Zhang
authors.forename: Gaia A
authors.initials: GA
authors.lastname: Scalabrino
authors.forename: Neil
authors.initials: N
authors.lastname: Frankish
authors.forename: Helen
authors.initials: H
authors.lastname: Sheridan
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000494:pharmacology*; D001565:Benzoates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007189:Indans / Q000737:chemistry* / Q000494:pharmacology*; D007192:Indenes / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: C576286:(1S)-1-phenylethanaminium 4-(((1S,2S)-1-hydroxy-2,3-dihydro-1H,1'H-(2,2'-biinden)-2-yl)methyl)benzoate; D000893:Anti-Inflammatory Agents; D001565:Benzoates; D007189:Indans; D007192:Indenes; C093582:indan