Abstract
The crystal packings of mono- (1) and dinitro derivatives (3) of methylcytizine are analyzed in terms of combined geometric and energy approaches and based on the evaluation of the degree of molecular deformation (a decrease in the molecular volume) in going from the free molecule to the crystal. An increase in the crystal density in going from the mono- to dinitro derivative (1.440 g cm−3 for 1 and 1.528 g cm−3 for 3 at 120 K) is associated with an increase in the density of the isolated molecule rather than with an increase in the packing density, which is almost equal in the crystals of compounds 1 and 3. The second-order nonlinear optical susceptibility of crystals was estimated in terms of a charge model, the prediction error of which is within 10%, being comparable with experimental accuracy. The similarity of the packing densities of compounds 1 and 3 enabled a detailed comparative analysis of the eff ect of the crystal fi eld on the nonlinear optical properties. Both compounds are characterized by relatively high nonlinear optical susceptibility, which is higher than that of urea, a commonly accepted standard, by a factor of 10 and 6.5 for compounds 1 and 3, respectively.
Similar content being viewed by others
References
L. R. Dalton, P. A. Sullivan, D. H. Bale, Chem. Rev., 2010, 110, 25.
K. Yu. Suponitsky, T. V. Timofeeva, M. Yu. Antipin, Russ. Chem. Rev., 2006, 75, 457.
F. Kajzar, J. Zyss, Nonlinear Opt., Quantum Opt., 2012, 43, 31.
L. E. Johnson, L. R. Dalton, B. H. Robinson, Acc. Chem. Res., 2014, 47, 3258.
T. W. Panunto, Z. Urbanczyk-Lipkowska, R. Johnson, M. C. Etter, J. Am. Chem. Soc., 1987, 109, 7786.
C. B. Aakeroy, N. R. Champness, C. Janiak, CrystEngComm, 2010, 12, 22.
I. V. Ananyev, M. G. Medvedev, S. M. Aldoshin, I. L. Eremenko, K. A. Lyssenko, Russ. Chem. Bull., 2016, 65, 1473.
K. Yu. Suponitsky, N. I. Burakov, A. L. Kanibolotsky, V. A. Mikhailov, J. Phys. Chem. A., 2016, 120, 4179.
G. M. Frankenbach, M. C. Etter, Chem. Mater., 1992, 4, 272.
K. Yu. Suponitsky, V. G. Tsirelson, D. Feil, Acta Crystallogr., 1999, A55, 821.
T. Steiner, Angew. Chem., Int. Ed., 2002, 41, 48.
A. B. Sheremetev, N. V. Palysaeva, M. I. Struchkova, K. Yu. Suponitsky, M. Yu. Antipin, Eur. J. Org. Chem., 2012, 2266.
A. E. Frumkin, N. V. Yudin, K. Yu. Suponitsky, A. B. Sheremetev, Mendeleev Commun., 2018, 28, 135.
A. Gavezzotti, Acc. Chem. Res., 1994, 27, 309.
J. D. Dunitz, Chem. Commun., 2003, 545.
W. D. S. Motherwell, H. L. Ammon, J. D. Dunitz, A. Dzyabchenko, P. Erk, A. Gavezzotti, D. W. M. Hofmann, F. J. J. Leusen, J. P. M. Lommerse, W. T. M. Mooij, S. L. Price, H. Scheraga, B. Schweizer, M. U. Schmidt, B. P. van Eijck, P. Verwer, D. E. Williams, Acta Crystallogr., 2002, B58, 647.
A. M. Reilly, R. I. Cooper, C. S. Adjiman, S. Bhattacharya, A. D. Boese, J. G. Brandenburg, P. J. Bygrave, R. Bylsma, J. E. Campbell, R. Car, D. H. Case, R. Chadha, J. C. Cole, K. Cosburn, H. M. Cuppen, F. Curtis, G. M. Day, R. A. DiStasio Jr, A. Dzyabchenko, B. P. van Eijck, D. M. Elking, J. A. van den Ende, J. C. Facelli, M. B. Ferraro, L. Fusti-Molnar, C.-A. Gatsiou, T. S. Gee, R. de Gelder, L. M. Ghiringhelli, H. Goto, S. Grimme, R. Guo, D. W. M. Hofmann, J. Hoja, R. K. Hylton, L. Iuzzolino, W. Jankiewicz, D. T. de Jong, J. Kendrick, N. J. J. de Klerk, H.-Y. Ko, L. N. Kuleshova, X. Li, S. Lohani, F. J. J. Leusen, A. M. Lund, J. Lv, Y. Ma, N. Marom, A. E. Masunov, P. McCabe, D. P. McMahon, H. Meekes, M. P. Metz, A. J. Misquitta, S. Mohamed, B. Monserrat, R. J. Needs, M. A. Neumann, J. Nyman, S. Obata, H. Oberhofer, A. R. Oganov, A. M. Orendt, G. I. Pagola, C. C. Pantelides, C. J. Pickard, R. Podeszwa, L. S. Price, S. L. Price, A. Pulido, M. G. Read, K. Reuter, E. Schneider, C. Schober, G. P. Shields, P. Singh, I. J. Sugden, K. Szalewicz, C. R. Taylor, A. Tkatchenko, M. E. Tuckerman, F. Vacarro, M. Vasileiadis, A. Vazquez-Mayagoitia, L. Vogt, Y. Wang, R. E. Watson, G. A. de Wijs, J. Yang, Q. Zhu, C. R. Groom, Acta Crystallogr., 2016, B72, 439.
M. C. Etter, K. S. Huang, Chem. Mater., 1992, 4, 824.
C. P. Brock, J. D. Dunitz, Chem. Mater., 1994, 6, 1118.
D. S. Chemla, J. Zyss, Nonlinear Optical Properties of Organic Molecules and Crystals, Acad. Press, Orlando, 1987.
J. L. Oudar, R. Hierle, J. Appl. Phys., 1977, 48, 2699.
T. V. Timofeeva, V. N. Nesterov, F. M. Dolgushin, Y. V. Zubavichus, J. T. Goldshtein, D. M. Sammeth, R. D. Clark, B. Penn, M. Yu. Antipin, Cryst. Eng., 2001, 3, 263.
M. V. Makarov, V. P. Dyadchenko, K. Yu. Suponitsky, D. A. Lemenovskii, M. Yu. Antipin, Russ. Chem. Bull., 2004, 53, 1942.
A. F. Smol’yakov, V. A. Karnoukhova, S. V. Osintseva, P. R. Petrova, A. V. Koval’skaya, I. P. Tsypysheva, Pharm. Chem., 2017, 50, 826.
I. P. Tsypysheva, A. V. Koval’skaya, A. N. Lobov, E. A. Nikolaeva, M. S. Yunusov, Chem. Nat. Compd., 2013, 49, 902.
E. G. Perez, C. Mendez-Galvez, B. K. Cassels, Nat. Prod. Rep., 2012, 29, 55.
O. B. Kazakova, D. V. Kazakov, E. Yu. Yamansarov, N. I. Medvedeva, G. A. Tolstikov, K. Yu. Suponitsky, D. E. Arkhipov, Tetrahedron Lett., 2011, 52, 976.
I. P. Tsypysheva, A. N. Lobov, A. V. Kovalskaya, V. I. Vinogradova, K. Yu. Suponitsky, S. L. Khursan, M. S. Yunusov, Tet. Assym., 2013, 24, 1318.
V. V. Shelkovnikov, I. Yu. Kargapolova, N. A. Orlova, S. V. Korotaev, A. E. Simanchuk, S. L. Mikerin, Russ. Chem. Bull., 2019, 58, 92.
I. P. Tsypysheva, A. V. Koval’skaya, A. N. Lobov, V. V. Zarubaev, L. A. Karpinskaya, I. A. Petrenko, E. A. Nikolaeva, A. A. Shtro, M. S. Yunusov, Chem. Nat. Compd., 2012, 48, 1042.
APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA, 2009.
G. M. Sheldrick, Acta Crystallogr., 2015, C71, 3.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, K. N. Kudin, Jr., J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision E.01, Gaussian, Inc., Wallingford, 2004.
J. Sponer, K. E. Riley, P. Hobza, PCCP, 2008, 10, 2595.
K. Yu. Suponitsky, K. A. Lyssenko, M. Yu. Antipin, N. S. Aleksandrova, A. B. Sheremetev, T. S. Novikova, Russ. Chem. Bull., 2009, 58, 2129.
Y. Zhao, N. E. Schultz, D. G. Truhlar, J. Chem. Theory Comput., 2006, 2, 364.
A. O. Dmitrienko, V. A. Karnoukhova, A. A. Potemkin, M. I. Struchkova, I. A. Kryazhevskikh, K. Yu. Suponitsky, Chem. Heterocyc. Compd., 2017, 53, 532.
R. F. W. Bader, Atoms in Molecules. A Quantum Theory, Clarendon Press, Oxford, 1990].
T. A. Keith, 2014, AIMAll, Version 14.11.23. TK Gristmill Software, Overland Park KS, USA (http://aim.tkgristmill.com).
Yu. V. Zefirov, P. M. Zorkii, Russ. Chem. Rev., 1995, 64, 415.
P. M. Zorkii, V. K. Bel’skii, S. G. Lazareva, M. A. Porai-Koshits, J. Struct. Chem., 1967, 8, 267.
J. D. Dunitz, A. Gavezzotti, Cryst. Growth. Des., 2005, 5, 2180.
O. V. Shishkin, V. V. Dyakonenko, A. V. Maleev, CrystEngComm., 2012, 14, 1795.
A. Romanova, K. Lyssenko, I. Ananyev, J. Computat. Chem., 2018, 39, 1607.
A. B. Sheremetev, B. V. Lyalin, A. M. Kozeev, N. V. Palysaeva, M. I. Struchkova, K. Yu. Suponitsky, RSC Adv., 2015, 5, 37617.
A. A. Gidaspov, V. V. Bakharev, K. Yu. Suponitsky, V. G. Nikitin, A. B. Sheremetev, RSC Adv., 2016, 6, 104325.
I. L. Dalinger, A. K. Shakhnes, K. A. Monogarov, K. Y. Suponitsky, A. B. Sheremetev, Mendeleev Commun., 2015, 25, 429.
I. V. Glukhov, K. A. Lyssenko, A. A. Korlyukov, M. Yu. Antipin, Russ. Chem. Bull., 2005, 54, 547.
D. G. Golovanov, K. A. Lyssenko, M. Yu. Antipin, Y. S. Vygodskii, E. I. Lozinskaya, A. S. Shaplov, CrystEngComm, 2005, 7, 53.
R. S. Rowland, R. Taylor, J. Phys. Chem., 1996, 100, 7384.
I. L. Dalinger, A. V. Kormanov, K. Yu. Suponitsky, N. V. Muravyev, A. B. Sheremetev, Chem. Asian J., 2018, 13, 1165.
I. L. Dalinger, O. V. Serushkina, N. V. Muravyev, D. B. Meerov, E. A. Miroshnichenko, T. S. Kon’kova, K. Yu. Suponitsky, M. V. Vener, A. B. Sheremetev, J. Mater. Chem. A, 2018, 6, 18669.
A. A. Larin, N. V. Muravyev, A. N. Pivkina, K. Yu. Suponitsky, I. V. Ananyev, D. V. Khakimov, L. L. Fershtat, N. N. Makhova, Chem. Eur. J., 2019, 25, 4225.
N. V. Palysaeva, A. G. Gladyshkin, I. A. Vatsadze, K. Yu. Suponitsky, D. E. Dmitriev, A. B. Sheremetev, Org. Chem. Front., 2019, 6, 249.
K. Yu. Suponitsky, S. Tafur, A. E. Masunov, J. Chem. Phys., 2008, 129, 044109.
K. Yu. Suponitsky, Y. Liao, A. E. Masunov, J. Phys. Chem. A, 2009, 113, 10994.
K. Yu. Suponitsky, A. E. Masunov, M. Yu. Antipin, Mendeleev. Commun., 2009, 19, 311.
M. H. Cardenuto, B. Champagne, PCCP, 2015, 17, 23634.
N. I. Shalin, O. D. Fominykh, M. Yu. Balakina, Chem. Phys. Lett., 2019, 717, 21.
K. Yu. Suponitsky, A. E. Masunov, M. Yu. Antipin, Mendeleev. Commun., 2008, 18, 265.
A. V. Vologzhanina, A. A. Golovanov, D. M. Gusev, I. S. Odin, R. A. Apreyan, K. Yu. Suponitsky, Cryst. Growth Des., 2014, 14, 4402.
J. L. Oudar, J. Zyss, Phys. Rev. A, 1982, 26, 2016.
J. Zyss, J. L. Oudar, Phys. Rev. A, 1982, 26, 2028.
A. V. Arzumanyan, I. K. Goncharova, R. A. Novikov, S. A. Milenin, K. L. Boldyrev, P. N. Solyev, Y. V. Tkachev, A. D. Volodin, A. F. Smol’yakov, A. A. Korlyukov, A. M. Muzafarov, Green Chem., 2018, 20, 1467.
A. I. Kitaigorodskii, Organic Chemical Crystallography, Consultants Bureau, New York, 1961.
A. B. Sheremetev, N. S. Aleksandrova, N. V. Palysaeva, M. I. Struchkova, V. A. Tartakovsky, K. Y. Suponitsky, Chem. Eur. J., 2013, 19, 12446.
A. B. Sheremetev, I. L. Yudin, N. V. Palysaeva, K. Yu. Suponitsky, J. Heterocycl. Chem., 2012, 49, 394.
I. L. Dalinger, K. Yu. Suponitsky, T. K. Shkineva, D. B. Lempert, A. B. Sheremetev, J. Mater. Chem. A, 2018, 6, 14780.
A. O. Dmitrienko, I. V. Ananyev, Russ. Chem. Bull., 2019, 68, 1.
Yu. V. Nelyubina, I. V. Glukhov, M. Yu. Antipin, K. A. Lyssenko, Chem. Commun., 2010, 46, 3469.
A. A. Gidaspov, V. A. Zalomlenkov, V. V. Bakharev, V. E. Parfenov, E. V. Yurtaev, M. I. Struchkova, N. V. Palysaeva, K. Yu. Suponitsky, D. B. Lempert, A. B. Sheremetev, RSC Adv., 2016, 6, 34921.
M. Gobel, T. M. Klapotke, Adv. Funct. Mater., 2009, 19, 347.
K. Yu. Suponitsky, K. A. Lyssenko, I. V. Ananyev, A. M. Kozeev, A. B. Sheremetev, Cryst. Growth Des., 2014, 14, 4439.
Y. Tang, C. He, G. H. Imler, D. A. Parrish, J. M. Shreeve, J. Mater. Chem. A, 2018, 6, 5136.
A. B. Sheremetev, V. L. Korolev, A. A. Potemkin, N. S. Aleksandrova, N. V. Palysaeva, T. H. Hoang, V. P. Sinditskii, K. Yu. Suponitsky, Asian J. Org. Chem., 2016, 5, 1388.
I. L. Dalinger, O. V. Serushkina, D. L. Lipilin, A. A. Anisimov, K. Yu. Suponitsky, A. B. Sheremetev, ChemPlusChem, 2019, 84, 802.
K. Yu. Suponitsky, A. E. Masunov, J. Chem. Phys., 2013, 139, 094310.
T. Seidler, K. Stadnicka, B. Champagne, Adv. Opt. Mater., 2014, 2, 1000.
L. G. Koreneva, V. F. Zolin, B. L. Davydov, Nelineinaya optika molekulyarnykh kristallov [Nonlinear Optics of Molecular Crystals], Nauka, Moscow, 1985 (in Russian).
A. Willetts, J. E. Rice, D. M. Burland, D. P. Shelton, J. Chem. Phys., 1992, 97, 7590.
Handbook of Advanced Electronic and Photonic Materials and Devices. Nonlinear Optical Materials, Ed. H. S. Nalwa, Academic Press, San Diego, 2000, Vol. 9.
I. L. Dalinger, I. A. Vatsadze, T. K. Shkineva, A. V. Kormanov, M. I. Struchkova, K. Yu. Suponitsky, A. A. Bragin, K. A. Monogarov, V. P. Sinditskii, A. B. Sheremetev, Chem. Asian J., 2015, 10, 1987.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0148–0157, January, 2020.
Rights and permissions
About this article
Cite this article
Smol’yakov, A.F., Osintseva, S.V., Mamin, E.A. et al. Crystal structure features of nitro derivatives of methylcytizine and their relationship with second-order nonlinear optical susceptibility. Russ Chem Bull 69, 148–157 (2020). https://doi.org/10.1007/s11172-020-2736-4
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-020-2736-4