Structure and conformation of 2 beta,3 beta-epoxyestr-5(10)-en-1,4, 17-trione, spectroscopic and X-ray crystallographic studies
Само за регистроване кориснике
2000
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Colourless single crystals were isolated as by-product during the synthesis of steroidal A-ring substituted 1,4-quinones (and epoxyquinols), as synthetic products with antibiotic and antitumor properties. Its structure was proposed by comparing IR, UV, H-1 and C-13 NMR spectra to the ones of quinone 2 and independently determined by an X-ray analysis, as 2 beta,3 beta-epoxyestr-5(10)-en-1,4,17-trione. Crystals belong to the monoclinic system with space group P2(1): a = 6.767(3) Angstrom, b = 7.097(5) Angstrom, 15.748(5) Angstrom, beta = 97.070(5)degrees, V = 750.6(8) Angstrom(3), Z = 2, D-x = 1.329 Mg m(-3), mu(Mo K-alpha) = 0.093 mm(-1). The structure was solved by direct methods and refined to a final R = 0.064 for 1729 reflections with I gt 2 sigma(I). The steroidal skeleton with chiral centre at C13 possesses the S configuration defining beta-orientation of O2 atom bridging C2 and C3 atoms and beta-oriented methyl group bonded to C13 atom. The best plane through the ring A and ep...oxy ring plane form an angle of 89.6(2)degrees. Conformational analysis of the steroid rings are performed by calculating the ring puckering parameters and asymmetry factors. The conformation of the A ring is screw-boat S-1(6), ring B half-chair H-4(3), ring C chair C-1(4), and the five-membered D ring is half-chair H-2(1) conformation. The crystal structure is stabilised by the weak C-H ... O hydrogen bonds and van der Waals interaction. (C) 2000 Elsevier Science B.V. All rights reserved.
Кључне речи:
NMR spectroscopy / X-ray crystallography / epoxide / steroidal quinonesИзвор:
Journal of Molecular Structure, 2000, 522, 289-301Издавач:
- Elsevier Science Bv, Amsterdam
DOI: 10.1016/S0022-2860(99)00363-4
ISSN: 0022-2860
WoS: 000086530500028
Scopus: 2-s2.0-0034636034
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Kapor, A AU - Ribar, B AU - Strumpel, M AU - Gasic, MJ AU - Milić, Dragana AU - Šolaja, Bogdan A. PY - 2000 UR - https://cherry.chem.bg.ac.rs/handle/123456789/387 AB - Colourless single crystals were isolated as by-product during the synthesis of steroidal A-ring substituted 1,4-quinones (and epoxyquinols), as synthetic products with antibiotic and antitumor properties. Its structure was proposed by comparing IR, UV, H-1 and C-13 NMR spectra to the ones of quinone 2 and independently determined by an X-ray analysis, as 2 beta,3 beta-epoxyestr-5(10)-en-1,4,17-trione. Crystals belong to the monoclinic system with space group P2(1): a = 6.767(3) Angstrom, b = 7.097(5) Angstrom, 15.748(5) Angstrom, beta = 97.070(5)degrees, V = 750.6(8) Angstrom(3), Z = 2, D-x = 1.329 Mg m(-3), mu(Mo K-alpha) = 0.093 mm(-1). The structure was solved by direct methods and refined to a final R = 0.064 for 1729 reflections with I gt 2 sigma(I). The steroidal skeleton with chiral centre at C13 possesses the S configuration defining beta-orientation of O2 atom bridging C2 and C3 atoms and beta-oriented methyl group bonded to C13 atom. The best plane through the ring A and epoxy ring plane form an angle of 89.6(2)degrees. Conformational analysis of the steroid rings are performed by calculating the ring puckering parameters and asymmetry factors. The conformation of the A ring is screw-boat S-1(6), ring B half-chair H-4(3), ring C chair C-1(4), and the five-membered D ring is half-chair H-2(1) conformation. The crystal structure is stabilised by the weak C-H ... O hydrogen bonds and van der Waals interaction. (C) 2000 Elsevier Science B.V. All rights reserved. PB - Elsevier Science Bv, Amsterdam T2 - Journal of Molecular Structure T1 - Structure and conformation of 2 beta,3 beta-epoxyestr-5(10)-en-1,4, 17-trione, spectroscopic and X-ray crystallographic studies VL - 522 SP - 289 EP - 301 DO - 10.1016/S0022-2860(99)00363-4 ER -
@article{ author = "Kapor, A and Ribar, B and Strumpel, M and Gasic, MJ and Milić, Dragana and Šolaja, Bogdan A.", year = "2000", abstract = "Colourless single crystals were isolated as by-product during the synthesis of steroidal A-ring substituted 1,4-quinones (and epoxyquinols), as synthetic products with antibiotic and antitumor properties. Its structure was proposed by comparing IR, UV, H-1 and C-13 NMR spectra to the ones of quinone 2 and independently determined by an X-ray analysis, as 2 beta,3 beta-epoxyestr-5(10)-en-1,4,17-trione. Crystals belong to the monoclinic system with space group P2(1): a = 6.767(3) Angstrom, b = 7.097(5) Angstrom, 15.748(5) Angstrom, beta = 97.070(5)degrees, V = 750.6(8) Angstrom(3), Z = 2, D-x = 1.329 Mg m(-3), mu(Mo K-alpha) = 0.093 mm(-1). The structure was solved by direct methods and refined to a final R = 0.064 for 1729 reflections with I gt 2 sigma(I). The steroidal skeleton with chiral centre at C13 possesses the S configuration defining beta-orientation of O2 atom bridging C2 and C3 atoms and beta-oriented methyl group bonded to C13 atom. The best plane through the ring A and epoxy ring plane form an angle of 89.6(2)degrees. Conformational analysis of the steroid rings are performed by calculating the ring puckering parameters and asymmetry factors. The conformation of the A ring is screw-boat S-1(6), ring B half-chair H-4(3), ring C chair C-1(4), and the five-membered D ring is half-chair H-2(1) conformation. The crystal structure is stabilised by the weak C-H ... O hydrogen bonds and van der Waals interaction. (C) 2000 Elsevier Science B.V. All rights reserved.", publisher = "Elsevier Science Bv, Amsterdam", journal = "Journal of Molecular Structure", title = "Structure and conformation of 2 beta,3 beta-epoxyestr-5(10)-en-1,4, 17-trione, spectroscopic and X-ray crystallographic studies", volume = "522", pages = "289-301", doi = "10.1016/S0022-2860(99)00363-4" }
Kapor, A., Ribar, B., Strumpel, M., Gasic, M., Milić, D.,& Šolaja, B. A.. (2000). Structure and conformation of 2 beta,3 beta-epoxyestr-5(10)-en-1,4, 17-trione, spectroscopic and X-ray crystallographic studies. in Journal of Molecular Structure Elsevier Science Bv, Amsterdam., 522, 289-301. https://doi.org/10.1016/S0022-2860(99)00363-4
Kapor A, Ribar B, Strumpel M, Gasic M, Milić D, Šolaja BA. Structure and conformation of 2 beta,3 beta-epoxyestr-5(10)-en-1,4, 17-trione, spectroscopic and X-ray crystallographic studies. in Journal of Molecular Structure. 2000;522:289-301. doi:10.1016/S0022-2860(99)00363-4 .
Kapor, A, Ribar, B, Strumpel, M, Gasic, MJ, Milić, Dragana, Šolaja, Bogdan A., "Structure and conformation of 2 beta,3 beta-epoxyestr-5(10)-en-1,4, 17-trione, spectroscopic and X-ray crystallographic studies" in Journal of Molecular Structure, 522 (2000):289-301, https://doi.org/10.1016/S0022-2860(99)00363-4 . .