Abstract
An unusual type of rac-7-chlorine-2,3,4a,6-tetrahydrofuro[2,3-b][1,4]oxathiin-6-one crystallization is reported. This compound crystallizes in the form of lamellar conglomerates where each single crystal is not optically pure but is only enantiomerically enriched by one optical antipode and displays optical rotation.
Similar content being viewed by others
REFERENCES
L. Péez-Garcia and D. B. Amabilino. Chem. Soc. Rev., 2002, 31, 342. https://doi.org/10.1039/B201099M
O. A. Lodochnikova, Y. K. Voronina, L. Z. Latypova, D. B. Krivolapov, A. R. Kurbangalieva, and I. A. Litvinov. Russ. Chem. Bull., 2013, 62, 1218. https://doi.org/10.1007/s11172-013-0167-1
O. A. Lodochnikova, A. R. Zaripova, R. R. Fayzullin, A. I. Samigullina, I. I. Vandyukova, L .N. Potapova, and A. R. Kurbangalieva. CrystEngComm, 2018, 20, 3218. https://doi.org/10.1039/C8CE00369F
D. P. Gerasimova, A. F. Saifina, D. V. Zakharychev, R. R. Fayzullin, A. R. Kurbangalieva, and O. A. Lodochnikova. CrystEngComm, 2021, 23, 3907. https://doi.org/10.1039/D1CE00227A
J. Jacques, A. Collet, and S. H. Wilen. Enantiomers, Racemates and Resolutions. Krieger Publishing Company: Malabar, Florida, 1994.
F. Dufour, C. Gervais, M. N. Petit, G. Perez, and G. Coquerel. J. Chem. Soc., Perkin Trans. 2, 2001, 2022. https://doi.org/10.1039/B100706H
V. Y. Torbeev, K. A. Lyssenko, O. N. Kharybin, M. Y. Antipin, and R. G. Kostyanovsky. J. Phys. Chem. B, 2003, 107, 13523. https://doi.org/10.1021/jp035588l
P. A. Maggard, A. L. Kopf, C. L. Stern, K. R. Poeppelmeier, K. M. Ok, and P. S. Halasyamani. Inorg. Chem., 2002, 41, 4852. https://doi.org/10.1021/ic0255712
R. J. Davey, S. N. Black, L. J. Williams, D. McEwan, and D. E. Sadler. J. Cryst. Growth, 1990, 102, 97. https://doi.org/10.1016/0022-0248(90)90890-W
L. Addadi, S. Weinstein, E. Gati, I. Weissbuch, and M. Lahav. J. Am. Chem. Soc., 1982, 104, 4610. https://doi.org/10.1021/ja00381a018
E. Heller and G. M. J. Schmidt. Isr. J. Chem., 1971, 9, 449. https://doi.org/10.1002/ijch.197100061
J. M. Thomas and J. O. Williams. Chem. Commun., 1967, 432. https://doi.org/10.1039/c19670000432
J. O. Williams and J. M. Thomas. Trans. Faraday Soc., 1967, 63, 1720. https://doi.org/10.1039/TF9676301720
H. D. Flack. Acta Crystallogr., Sect. A: Found. Crystallogr., 1983, 39, 876. https://doi.org/10.1107/S0108767383001762
H. D. Flack and G. Bernardinelli. J. Appl. Crystallogr., 2000, 33, 1143. https://doi.org/10.1107/S0021889800007184
M. V. Zlokazov and K. K. Pivnitsky. Mendeleev Commun., 2020, 30, 1. https://doi.org/10.1016/j.mencom.2020.01.001
R. H. Martin and M. J. Marchant. Tetrahedron, 1974, 30, 343. https://doi.org/10.1016/S0040-4020(01)91468-1
B. S. Green and M. Knossow. Science, 1981, 214, 795. https://doi.org/10.1126/science.214.4522.795
K. Claborn, E. Puklin-Faucher, M. Kurimoto, W. Kaminsky, and B. Kahr. J. Am. Chem. Soc., 2003, 125, 14825. https://doi.org/10.1021/ja035644w
E. V. Mironova, O. A. Lodochnikova, D. B. Krivolapov, I. A. Litvinov, Y. V. Veremeichik, and V. V. Plemenkov.J. Struct. Chem., 2014, 55(3), 539. https://doi.org/10.1134/S0022476614030238
L. Z. Latypova, E. Sh. Saigitbatalova, D. R. Chulakova, O. A. Lodochnikova, A. R. Kurbangalieva, E. A. Berdnikov, and G. A. Chmutova. Russ. J. Org. Chem., 2014, 50, 521. https://doi.org/10.1134/S1070428014040149
N. F. Devyatova, L. S. Kosolapova, A. R. Kurbangalieva, E. A. Berdnikov, O. A. Lodochnikova, I. A. Litvinov, and G. A. Chmutova. Russ. J. Org. Chem., 2008, 44, 1225. https://doi.org/10.1134/S1070428008080204
APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program (Version 7.31A). Bruker AXS: Madison, Wisconsin, USA, 2006.
G. M. Sheldrick. SADABS. Bruker AXS: Madison, WI, USA, 1997.
G. M. Sheldrick. Acta Crystallogr., Sect. A: Found. Adv., 2015, 71, 3. https://doi.org/10.1107/S2053273314026370
G.M. Sheldrick. Acta Crystallogr., Sect. C: Struct. Chem., 2015, 71, 3. https://doi.org/10.1107/S2053229614024218
L. J. Farrugia. J. Appl. Crystallogr., 2012, 45, 849. https://doi.org/10.1107/S0021889812029111
A. L. Spek. Acta Crystallogr., Sect. D: Biol. Crystallogr., 2009, 65, 148. https://doi.org/10.1107/S090744490804362X
C. F. Macrae, I. Sovago, S. J. Cottrell, P. T. A. Galek, P. McCabe, E. Pidcock, M. Platings, G. P. Shield, J. S. Stevens,M. Towler, and P. A. Wood. J. Appl. Crystallogr., 2020, 53, 226. https://doi.org/10.1107/S1600576719014092
S. Parsons, H. D. Flack, and T. Wagner. Acta Crystallogr., Sect. B: Struct. Sci., 2013, 69, 249. https://doi.org/10.1107/S2052519213010014
J. P. M. Lommerse, A. J. Stone, R. Taylor, and F. H. Allen. J. Am. Chem. Soc., 1996, 118, 3108. https://doi.org/10.1021/ja953281x
P. Cimino, M. Pavone, and V. Barone. J. Phys. Chem. A, 2007, 111, 8482. https://doi.org/10.1021/jp073567b
K. E. Riley and P. Hobza. J. Chem. Theory Comput., 2008, 4, 232. https://doi.org/10.1021/ct700216w
O. A. Lodochnikova, L. Z. Latypova, R. M. Khakimov, A. R. Kurbangalieva, D. B. Krivolapov, and I. A. Litvinov.J. Struct. Chem., 2013, 54(1), 213. https://doi.org/10.1134/S0022476613010356
R. R. Fayzullin, S. A. Shteingolts, O. A. Lodochnikova, V. L. Mamedova, D. E. Korshin, and V. A. Mamedov. CrystEngComm, 2019, 21, 1587. https://doi.org/10.1039/C8CE02132E
Funding
The work was funded by the State Assignment for FRC Kazan Scientific Center of RAS.
The synthesis of the main compound was funded by the Ministry of Education and Science of the Russian Federation (grant for the Kazan Federal University within the State Assignment in the field of scientific activity No.0671-2020-0063).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflict of interests.
Additional information
Russian Text © The Author(s), 2021, published in Zhurnal Strukturnoi Khimii, 2021, Vol. 62, No. 9, pp. 1522-1528.https://doi.org/10.26902/JSC_id79938
Rights and permissions
About this article
Cite this article
Gerasimova, D.P., Lodochnikova, O.A., Kurbangalieva, A.R. et al. RACEMIC TWINNING OF 7-CHLORINE-2,3,4a,6- TETRAHYDROFURO[2,3-b][1,4]OXATHIIN-6-ONE CRYSTALS. J Struct Chem 62, 1425–1431 (2021). https://doi.org/10.1134/S0022476621090110
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0022476621090110