Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.003 Å; R factor = 0.030; wR factor = 0.099; data-to-parameter ratio = 18.5.In the title compound, C 6 H 8 NO + ÁHSO 4 À , there is an intricate cation-cation, cation-anion and anion-anion three-dimensional hydrogen-bond network. Refinement R[F 2 > 2(F 2 )] = 0.030 wR(F 2 ) = 0.099 S = 1.14 2241 reflections 121 parameters 1 restraint H-atom parameters constrained Á max = 0.32 e Å À3 Á min = À0.45 e Å À3 Absolute structure: Flack (1983), with 1095 Friedel pairs Flack parameter: À0.02 (8) organic compounds
The asymmetric unit of the title compound, C7H10N+·NO3 −, consists of a 4-methylanilinium cation protonated at the amino group and a nitrate anion. In the crystal, anions and cations are linked through N—H⋯O and N—H⋯(O,O) hydrogen bonds, buiding a corrugated layer structure parallel to (001).
The aim of the study of optical resolution processes is to achieve a more efficient and less time consuming way of enantiomer separation. Supercritical fluid extraction as an alternative green technology for optical isomer separation was applied for the resolution of ibuprofen. Ibuprofen is widely used as non-steroidal anti-inflammatory drug. The resolution of ibuprofen (1) with the mixture of (+)-(R)-phenylethylamine (2) and benzylamine (3) was compared to the results obtained without the achiral additive [1]. Single crystal X-ray studies were performed on the salts of (+)-(R)-phenylethylamine crystallized with (-)-(R)-ibuprofen (4) and (+)-(S)-ibuprofen (5) as well as on the co-crystal resulted from the crystallisation of the racemic ibuprofen with the achiral benzylamine (6) in order to study the influence of the structurally similar achiral additive. (+)-(R)-phenylethylamine crystallises with (-)-(R)ibuprofen and (+)-(S)-ibuprofen, respectively with 1:1 stoichiometry. Unexpectedly, the crystal of the benzylamineibuprofen salt contains an additional neutral ibuprofen molecule thus having 1:2 stoichiometry obtaining both from solution crystallisation and by mass balance calculation of the supercritical fluid CO 2 extraction. The lack of the methyl moiety in the benzylamine in structure (6) compared to the (+)-(R)-phenylethylamine molecule in structures (4) and (5) results a sterically favourable closer packing, higher crystal density. There is enough space in crystal (6) close to the ladder like hydrogen bond column to bond a neutral ibuprofen molecule as end group in the low acidity medium.
Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.004 Å; R factor = 0.050; wR factor = 0.135; data-to-parameter ratio = 18.7.The crystal structure of the title compound, C 7 H 10 N + ÁNO 3 À , consists of anion-cation layers parallel to the (100) plane, generated by N-HÁ Á ÁO hydrogen bonds. 16 of the 22 atoms (the exceptions being two O and four H atoms) lie on a mirror plane. Related literatureFor related structures see: Benali-Cherif, Direm et al. (2007); Benali-Cherif, Allouche et al. (2007); Bendeif et al. (2007).Experimental Crystal data C 7 H 10 N + ÁNO 3 À M r = 170.17 Orthorhombic, Pnma a = 16.5632 (2) Å b = 6.7242 (2) Å c = 7.6849 (3) Å V = 855.90 (4) Å 3 Z = 4 Mo K radiation = 0.10 mm À1 T = 293 (2) K 0.15 Â 0.1 Â 0.05 mm Data collection Nonius KappaCCD diffractometer Absorption correction: none 9040 measured reflections 1331 independent reflections 895 reflections with I > 2(I) R int = 0.075
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.