Abstract
The structures of 1,4-diiodo-2,5-dimethylbenzene (1) and 1,3,4,6-tetraiodo-2,5-dimethylbenzene (2) are determined by single crystal X-ray diffraction. The packing motif in 2 is mainly determined by π-stacking and the system of halogen⋯halogen contacts between the stacks. In the structure of 1, it is determined by the presence of both π-stacking and the interaction between σ-holes of iodine atoms and the π-system of the neighboring molecules. The thermal stability of 1 and 2 is studied and the optical spectra are measured.
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REFERENCES
G. L. Ciamician and M. Dennstedt. Ber. Dtsch. Chem. Ges., 1882, 15, 2579-2585. https://doi.org/10.1002/cber.188201502221
E. Rupp. Ber. Dtsch. Chem. Ges., 1896, 29, 1625-1634. https://doi.org/10.1002/cber.18960290293
M. A. Bondarenko, A. S. Novikov, P. A. Abramov, I. F. Sakhapov, M. N. Sokolov, and S. A. Adonin. J. Mol. Struct., 2021, 1230, 129931. https://doi.org/10.1016/j.molstruc.2021.129931
E. V. Bartashevich and V. G. Tsirelson. Russ. Chem. Rev., 2014, 83, 1181-1203. https://doi.org/10.1070/RCR4440
E. V. Bartashevich, E. A. Grigoreva, I. D. Yushina, L. M. Bulatova, and V. G. Tsirelson. Russ. Chem. Bull., 2017, 66, 1345-1356. https://doi.org/10.1007/s11172-017-1898-1
G. Cavallo, P. Metrangolo, R. Milani, T. Pilati, A. Priimagi, G. Resnati, and G. Terraneo. Chem. Rev., 2016, 116, 2478-2601. https://doi.org/10.1021/acs.chemrev.5b00484
D. M. Ivanov, M. A. Kinzhalov, A. S. Novikov, I. V. Ananyev, A. A. Romanova, V. P. Boyarskiy, M. Haukka, and V. Y. Kukushkin. Cryst. Growth Des., 2017, 17, 1353-1362. https://doi.org/10.1021/acs.cgd.6b01754
A. S. Mikherdov, A. S. Novikov, V. P. Boyarskiy, and V. Y. Kukushkin. Nat. Commun., 2020, 11, 2921. https://doi.org/10.1038/s41467-020-16748-x
A. A. Eliseeva, D. M. Ivanov, A. S. Novikov, A. V. Rozhkov, I. V. Kornyakov, A. Y. Dubovtsev, and V. Y. Kukushkin. Dalton Trans., 2020, 49, 356-367. https://doi.org/10.1039/C9DT04221K
A. S. Novikov, D. M. Ivanov, Z. M. Bikbaeva, N. A. Bokach, and V. Y. Kukushkin. Cryst. Growth Des., 2018, 18, 7641-7654. https://doi.org/10.1021/acs.cgd.8b01457
Y. V. Matveychuk, M. V. Ilkaeva, E. A. Vershinina, V. I. Batalov, R. S. Morozov, and E. V. Bartashevich. J. Mol. Struct., 2016, 1119, 227-234. https://doi.org/10.1016/j.molstruc.2016.04.072
I. Yushina, N. Tarasova, D. Kim, V. Sharutin, and E. Bartashevich. Crystals, 2019, 9, 506. https://doi.org/10.3390/cryst9100506
U. Dabranskaya, D. M. Ivanov, A. S. Novikov, Y. V. Matveychuk, N. A. Bokach, and V. Y. Kukushkin. Cryst. Growth Des., 2019, 19, 1364-1376. https://doi.org/10.1021/acs.cgd.8b01757
M. A. Kinzhalov, M. V. Kashina, A. S. Mikherdov, E. A. Mozheeva, A. S. Novikov, A. S. Smirnov, D. M. Ivanov, M. A. Kryukova, A. Y. Ivanov, S. N. Smirnov, V. Y. Kukushkin, and K. V. Luzyanin. Angew. Chem., Int. Ed., 2018, 57, 12785-12789. https://doi.org/10.1002/anie.201807642
Y. V. Torubaev and I. V. Skabitsky. Z. Kristallogr. – Cryst. Mater., 2020, 235, 599-607. https://doi.org/10.1515/zkri-2020-0064
Y. V. Torubaev, I. V. Skabitsky, and K. A. Lyssenko. Mendeleev Commun., 2020, 30, 580-582. https://doi.org/10.1016/j.mencom.2020.09.009
A. S. Novikov, D. M. Ivanov, M. S. Avdontceva, and V. Y. Kukushkin. CrystEngComm, 2017, 19, 2517-2525. https://doi.org/10.1039/C7CE00346C
E. Albright, J. Cann, A. Decken, and S. Eisler. CrystEngComm, 2017, 19, 1024-1027. https://doi.org/10.1039/C6CE02339H
A. A. Eliseeva, D. M. Ivanov, A. S. Novikov, and V. Y. Kukushkin. CrystEngComm, 2019, 21, 616-628. https://doi.org/10.1039/C8CE01851K
S. V. Baykov, S. I. Filimonov, A. V. Rozhkov, A. S. Novikov, I. V. Ananyev, D. M. Ivanov, and V. Y. Kukushkin. Cryst. Growth Des., 2020, 20, 995-1008. https://doi.org/10.1021/acs.cgd.9b01334
P. A. Demakov, S. A. Sapchenko, D. G. Samsonenko, D. N. Dybtsev, and V. P. Fedin. Russ. Chem. Bull., 2018, 67, 490-496. https://doi.org/10.1007/s11172-018-2098-3
V. A. Bolotov, K. A. Kovalenko, D. G. Samsonenko, X. Han, X. Zhang, G. L. Smith, L. J. MCormick, S. J. Teat, S. Yang, M. J. Lennox, A. Henley, E. Besley, V. P. Fedin, D. N. Dybtsev, and M. Schröder. Inorg. Chem., 2018, 57, 5074-5082. https://doi.org/10.1021/acs.inorgchem.8b00138
A. V. Marakulin, A. A. Lysova, D. G. Samsonenko, P. V. Dorovatovskii, V. A. Lazarenko, D. N. Dybtsev, and V. P. Fedin. Russ. Chem. Bull., 2020, 69, 360-368. https://doi.org/10.1007/s11172-020-2768-9
A. A. Sapianik, E. N. Zorina-Tikhonova, M. A. Kiskin, D. G. Samsonenko, K. A. Kovalenko, A. A. Sidorov, I. L. Eremenko, D. N. Dybtsev, A. J. Blake, S. P. Argent, M. Schröder, and V. P. Fedin. Inorg. Chem., 2017, 56, 1599-1608. https://doi.org/10.1021/acs.inorgchem.6b02713
K. deKrafft, Z. Xie, G. Cao, S. Tran, L. Ma, O. Zhou, and W. Lin. Angew. Chem., Int. Ed., 2009, 48, 9901-9904. https://doi.org/10.1002/anie.200904958
M. A. Rahman, F. Shito, and T. Kitamura. Synthesis, 2010, 27-29. https://doi.org/10.1055/s-0029-1217072
E. R. T. Tiekink. CrystEngComm, 2021, 23, 904-928. https://doi.org/10.1039/D0CE01677B
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The work was supported by the Russian Science Foundation (grant No. 21-73-20019).
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Russian Text © The Author(s), 2022, published in Zhurnal Strukturnoi Khimii, 2022, Vol. 63, No. 4, pp. 504-509.https://doi.org/10.26902/JSC_id90869
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Rajakumar, K., Sharutin, V.V., Adonin, S.A. et al. DI- AND TETRAIODOXYLENES: STRUCTURE AND FEATURES OF NON-COVALENT INTERACTIONS IN A SOLID STATE. J Struct Chem 63, 620–625 (2022). https://doi.org/10.1134/S0022476622040138
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DOI: https://doi.org/10.1134/S0022476622040138