Abstract
The review concerns methods for modeling the crystal structure of polynitrogen compounds and their cocrystals. The state of the art in chemical research into (co)crystals of energetic compounds is described. Various structure modeling methods (including original ones) are considered and analyzed, and criteria for cocrystal formation at different co-former ratios are proposed. The results are discussed of studies on the search for crystal packings of various polynitrogen compounds and their cocrystals, on prediction of the possibility of cocrystal formation, and targeted synthesis of new substances. The predictive power of the developed structure modeling methods is confirmed by the results of X-ray diffraction studies of the synthesized cocrystals. Prospects for application of certain cocrystals as a basis for energetic materials are outlined.
References
A. I. Kitaigorodsky, Mixed Crystals [Springer Series in Solid-State Sciences, Vol. 33], Springer-Verlag, Berlin, 1984, 404 pp.
E. A. Losev, B. A. Zakharov, T. N. Drebushchak, E. V. Boldyreva, Acta Crystallogr., Sect. C, 2011, 67, o297; DOI: https://doi.org/10.1107/S0108270111024620.
B. A. Zakharov, B. A. Kolesov, E. V. Boldyreva, Phys. Chem. Chem. Phys., 2011, 13, 13106; DOI: https://doi.org/10.1039/C1CP20599D.
W. Zhu, X. Zhang, W. Hu, Sci. Bull., 2021, 66, 512; DOI: https://doi.org/10.1016/J.SCIB.2020.07.034.
L. Sun, Y. Wang, F. Yang, X. Zhang, W. Hu, Adv. Mater., 2019, 31, 1902328; DOI: https://doi.org/10.1002/adma.201902328.
J. Zhang, W. Xu, P. Sheng, G. Zhao, D. Zhu, Acc. Chem. Res., 2017, 50, 1654; DOI: https://doi.org/10.1021/acs.accounts.7b00124.
A. Karagianni, M. Malamatari, K. Kachrimanis, Pharmaceutics, 2018, 10, 18; DOI: https://doi.org/10.3390/pharmaceutics10010018.
G. Bolla, B. Sarma, A. K. Nangia, Chem. Rev., 2022, 122, 11514; DOI: https://doi.org/10.1021/acs.chemrev.1c00987.
A. O. Surov, A. G. Ramazanova, A. P. Voronin, K. V. Drozd, A. V. Churakov, G. L. Perlovich, Pharma ceutics, 2023, 15, 836; DOI: https://doi.org/10.3390/pharmaceutics15030836.
A. O. Surov, A. P. Voronin, K. V. Drozd, M. S. Gruzdev, G. L. Perlovich, J. Prashanth, S. Balasubramanian, Phys. Chem. Chem. Phys., 2021, 23, 9695; DOI: https://doi.org/10.1039/D1CP00793A.
A. Shaik, P. U. Bhagwat, P. Palanisamy, D. Chhabria, P. Dubey, S. Kirubakaran, V. Tiruvenkatam, CrystEngComm, 2023, 25, 2570; DOI: https://doi.org/10.1039/D3CE00056G.
J. C. Bennion, A. J. Matzger, Acc. Chem. Res., 2021, 54, 1699; DOI: https://doi.org/10.1021/acs.accounts.0c00830.
M. Sultan, J. Wu, I. Ul Haq, M. Imran, L. Yang, J. J. Wu, J. Lu, L. Chen, Molecules, 2022, 27, 4775; DOI: https://doi.org/10.3390/molecules27154775.
N. V. Muravyev, L. L. Fershtat, I. L. Dalinger, K. Yu. Suponitsky, I. V. Ananyev, I. N. Melnikov, Cryst. Growth Des., 2022, 22, 7349; DOI: https://doi.org/10.1021/acs.cgd.2c00964.
G. Liu, S.-H. Wei, C. Zhang, Cryst. Growth Des., 2020, 20, 7065; DOI: https://doi.org/10.1021/acs.cgd.0c01097.
J. D. Dunitz, A. Gavezzotti, Cryst. Growth Des., 2012, 12, 5873; DOI: https://doi.org/10.1021/cg301293r.
A. Mukherjee, G. R. Desiraju, Cryst. Growth Des., 2014, 14, 1375; DOI: https://doi.org/10.1021/cg401851z.
Y. Jiang, Z. Yang, J. Guo, H. Li, Y. Liu, Y. Guo, M. Li, X. Pu, Nat. Commun., 2021, 12, 5950; DOI: https://doi.org/10.1038/s41467-021-26226-7.
J. Maddox, Nature, 1988, 335, 201; DOI: https://doi.org/10.1038/335201a0.
A. Gavezzotti, G. Filippini, Synth. Met., 1991, 40, 257; DOI: https://doi.org/10.1016/0379-6779(91)91781-5.
D. E. Williams, PCK83: A Crystal Molecular Packing Analysis Program, QCPE, Indiana University, Bloomington, Indiana, 1984.
E. O. Pyzer-Knapp, H. P. G. Thompson, G. M. Day, Acta Crystallogr., Sect. B, 2016, 72, 477; DOI: https://doi.org/10.1107/S2052520616007708.
A. N. Razdol’skii, N. E. Artem’eva, T. S. Pivina, V. A. Shlyapochnikov, Bull. Acad. Sci. USSR. Div. Chem. Sci., 1985, 34, 1872; DOI: https://doi.org/10.1007/BF00953926.
T. S. Pivina, V. V. Shcherbukhin, M. S. Molchanova, N. S. Zefirov, Propellants, Explos. Pyrotech., 1995, 20, 144; DOI: https://doi.org/10.1002/prep.19950200309.
M. S. Molchanova, Cand. Sci. (Chem.) Thesis, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 1997, 149 pp. (in Russian).
F. A. Momany, L. M. Carruthers, H. A. Scheraga, J. Phys. Chem., 1974, 78, 1621; DOI: https://doi.org/10.1021/j100609a006.
A. V. Dzyabchenko, Russ. J. Phys. Chem. A, 2008, 82, 1663; DOI: https://doi.org/10.1134/S0036024408100075.
A. V. Dzyabchenko, T. S. Pivina, E. A. Arnautova, J. Mol. Struct., 1996, 378, 67; DOI: https://doi.org/10.1016/0022-2860(95)09165-3.
D. J. Edwards, in Proc. 6th Int. Symp. Deton., Colorado, CA, USA, 1976.
S. A. Gubin, V. V. Odintsov, V. A. Shargatov, V. I. Pepekin, Dokl. Chem., 1981, 261, 592 (in Russian).
A. S. Smirnov, S. P. Smirnov, T. S. Pivina, D. B. Lempert, L. K. Maslova, Russ. Chem. Bull., 2016, 65, 2315; DOI: https://doi.org/10.1007/s11172-016-1584-8.
M. S. Molchanova, T. S. Pivina, E. A. Arnautova, N. S. Zefirov, J. Mol. Struct. (THEOCHEM), 1999, 465, 11; DOI: https://doi.org/10.1016/S0166-1280(98)00200-0.
K. I. Rezchikova, A. M. Churakov, V. A. Shlyapochnikov, V. A. Tartakovsky, Russ. Chem. Bull., 1999, 48, 870; DOI: https://doi.org/10.1007/bf02494628.
H. Shechter, Synthesis of High Energy 1,2,3,4-Tetrazine-1,3-Di-N-Oxides and Pentazine Poly-N-Oxides, Rpt. AFRL-SR-AR-TR-05-0032, Air Force Research Laboratory, Wright-Patterson Air, 2004.
J. L. Mendoza-Cortes, Q. An, W. A. Goddard III, C. Ye, S. Zybin, J. Comput. Chem., 2016, 37, 163; DOI: https://doi.org/10.1002/jcc.23893.
M. S. Klenov, A. A. Guskov, O. V. Anikin, A. M. Churakov, Yu. A. Strelenko, I. V. Fedyanin, K. A. Lyssenko, V. A. Tartakovsky, Angew. Chem., Int. Ed., 2016, 55, 11472; DOI: https://doi.org/10.1002/anie.201605611.
D. V. Khakimov, A. V. Dzyabchenko, T. S. Pivina, Russ. Chem. Bull., 2020, 69, 212; DOI: https://doi.org/10.1007/s11172-020-2748-0.
D. V. Khakimov, A. V. Dzyabchenko, T. S. Pivina, Propellants, Explos. Pyrotech., 2019, 44, 1528; DOI: https://doi.org/10.1002/prep.201900252.
Z. Yang, S. Yang, G. Li, J. Lin, Acta Phys.-Chim. Sin., 2007, 23, 285; DOI: https://doi.org/10.1016/S1872-1508(07)60020-5.
A. V. Dzyabchenko, D. V. Khakimov, T. S. Pivina, Gorenie i vzryv [Combustion and Explosion], 2016, 9, No. 2, 128 (in Russian).
D. V. Khakimov, L. L. Fershtat, T. S. Pivina, N. N. Makhova, J. Phys. Chem. A, 2021, 125, 3920; DOI: https://doi.org/10.1021/acs.jpca.1c02960.
D. V. Khakimov, V. P. Zelenov, T. S. Pivina, J. Comput. Chem., 2022, 43, 778; DOI: https://doi.org/10.1002/jcc.26833.
C. Wei, H. Huang, X. Duan, C. Pei, Propellants, Explos. Pyrotech., 2011, 36, 416; DOI: https://doi.org/10.1002/prep.201000022.
H. Lin, Sh.-G. Zhu, H.-Z. Li, X.-H. Peng, J. Phys. Org. Chem., 2013, 26, 898; DOI: https://doi.org/10.1002/poc.3188.
S. Zhang, H. Zhao, Adv. Mater. Res., 2014, 900, 251; DOI: https://doi.org/10.4028/www.scientific.net/AMR.900.251.
R. A. Wiscons, A. J. Matzger, Cryst. Growth Des., 2017, 17, 901; DOI: https://doi.org/10.1021/acs.cgd.6b01766.
Y.-J. Wei, F.-D. Ren, W.-J. Shi, Q. Zhao, J. Energ. Mater., 2016, 34, 426; DOI: https://doi.org/10.1080/07370652.2015.1115917.
G. Han, R-j. Gou, F-d. Ren, S-h. Zhang, C-l. Wu, S-f. Zhu, Comput. Theor. Chem., 2017, 1109, 27; DOI: https://doi.org/10.1016/j.comptc.2017.03.044.
G.-y. Hang, W.-l. Yu, T. Wang, J.-t. Wang, Z. Li, J. Mol. Model., 2017, 23, 30; DOI: https://doi.org/10.1007/s00894-016-3193-8.
G.-y. Hang, J.-t. Wang, T. Wang, H.-m. Shen, W.-l. Yu, R.-q. Shen, J. Mol. Model., 2022, 28, 58; DOI: https://doi.org/10.1007/s00894-022-05049-3.
G.-Y. Hang, W.-L. Yu, T. Wang, J.-T. Wang, Z. Li, Theor. Chem. Acc., 2018, 137, 114; DOI: https://doi.org/10.1007/s00214-018-2297-x.
Y. Yu, Sh. Miao, K. Jia, H. Wang, W. Qin, S. Jing, Propellants, Explos. Pyrotech., 2023, 48, e202200280; DOI: https://doi.org/10.1002/PREP.202200280.
K. Yu. Suponitsky, I. V. Fedyanin, V. A. Karnoukhova, V. A. Zalomlenkov, A. A. Gidaspov, V. V. Bakharev, A. B. Sheremetev, Molecules, 2021, 26, 7452; DOI: https://doi.org/10.3390/molecules26247452.
N. A. Mir, R. Dubey, G. R. Desiraju, Acc. Chem. Res., 2019, 52, 2210; DOI: https://doi.org/10.1021/acs.accounts.9b00211.
K. Wang, W. Zhu, Comput. Mater. Sci., 2020, 178, DOI: https://doi.org/10.1016/j.commatsci.2020.109643.
R. F. B. Gonçalves, A. Kuznetsov, B. T. Rocco, L. Rocco, J. A. F. F. Rocco, Comput. Theor. Chem., 2022, 1212, 113723; DOI: https://doi.org/10.1016/j.comptc.2022.113723.
F. Wang, G. Du, X. Liu, M. Shao, C. Zhang, L. Chen, Nanotechnol. Rev., 2022, 11, 2141; DOI: https://doi.org/10.1515/ntrev-2022-0124.
M. Pakhnova, I. Kruglov, A. Yanilkin, A. R. Oganov, Phys. Chem. Chem. Phys., 2020, 22, 16822; DOI: https://doi.org/10.1039/d0cp03042b.
A. O. Lyakhov, A. R. Oganov, H. T. Stokes, Q. Zhu, Comput. Phys. Commun., 2013, 184, 1172; DOI: https://doi.org/10.1016/j.cpc.2012.12.009.
Th. P. Senftle, S. Hong, M. M. Islam, S. B. Kylasa, Y. Zheng, Y. K. Shin, Ch. Junkermeier, R. Engel-Herbert, M. J. Janik, H. M. Aktulga, T. Verstraelen, A. Grama, A. C. T. van Duin, Npj Comput. Mater., 2016, 2, 15011; DOI: https://doi.org/10.1038/npjcompumats.2015.11.
J. Hafner, J. Comput. Chem., 2008, 29, 2044; DOI: https://doi.org/10.1002/jcc.21057.
A. V. Dzyabchenko, J. Struct. Chem. (USSR), 1984, 25, 416; DOI: https://doi.org/10.1007/BF00749334.
R. J. Gdanitz, Chem. Phys. Lett., 1992, 190, 391; DOI: https://doi.org/10.1016/0009-2614(92)85357-G.
H. R. Karfunkel, F. J. J. Leusen, R. J. Gdanitz, J. Comput. Aided Mater. Des., 1994, 1, 177; DOI: https://doi.org/10.1007/BF00708708.
J. R. Holden, Z. Du, H. L. Ammon, J. Comput. Chem., 1993, 14, 422; DOI: https://doi.org/10.1002/jcc.540140406.
M. A. Neumann, C. Tedesco, S. Destri, D. R. Ferro, W. Porzio, J. Appl. Crystallogr., 2002, 35, 296; DOI: https://doi.org/10.1107/S0021889802002844.
G. M. Day, W. D. S. Motherwell, W. Jones, Phys. Chem. Chem. Phys., 2007, 9, 1693; DOI: https://doi.org/10.1039/b612190j.
C. Ouvrard, S. L. Price, Cryst. Growth Des., 2004, 4, 1119; DOI: https://doi.org/10.1021/cg049922u.
G. M. Day, J. Chisholm, N. Shan, W. D. S. Motherwell, W. Jones, Cryst. Growth Des., 2004, 4, 1327; DOI: https://doi.org/10.1021/cg0498148.
B. P. van Eijck, Phys. Chem. Chem. Phys., 2002, 4, 4789; DOI: https://doi.org/10.1039/b206088d.
A. J. Pertsin, A. I. Kitaigorodsky, The Atom-Atom Potential Method. Application to Organic Molecular Solids (Springer Series in Chemical Physics, Vol. 43), Ed. M. Cardona, Springer-Verlag, Berlin, Heidelberg, 1987; DOI: https://doi.org/10.1007/978-3-642-82712-9_1.
A. I. Kitaygorodsky, Tetrahedron, 1961, 14, 230; DOI: https://doi.org/10.1016/S0040-4020(01)92172-6.
D. E. Williams, J. Chem. Phys., 1966, 45, 3770; DOI: https://doi.org/10.1063/1.1727399.
D. E. Williams, Acta Crystallogr., Sect. A, 1972, 28, 84; DOI: https://doi.org/10.1107/S0567739472000178.
D. S. Coombes, Philos. Mag. B, 1996, 73, 117; DOI: https://doi.org/10.1080/13642819608239117.
D. S. Coombes, S. L. Price, D. J. Willock, M. Leslie, J. Phys. Chem., 1996, 100, 7352; DOI: https://doi.org/10.1021/jp960333b.
D. E. Williams, D. J. Houpt, Acta Crystallogr., Sect. B, 1986, 42, 286; DOI: https://doi.org/10.1107/S010876818609821X.
A. Abraha, D. E. Williams, Inorg. Chem., 1999, 38, 4224; DOI: https://doi.org/10.1021/ic990573g.
D. E. Williams, J. Comput. Chem., 2001, 22, 1; DOI: https://doi.org/10.1002/1096-987X(20010115)22:1<1::AID-JCC2>3.0.CO;2-6.
D. E. Williams, J. Comput. Chem., 2001, 22, 1154; DOI: https://doi.org/10.1002/jcc.1074.
G. M. Day, S. L. Price, J. Am. Chem. Soc., 2003, 125, 16434; DOI: https://doi.org/10.1021/ja0383625.
A. Jagielska, Ye. A. Arnautova, H. A. Scheraga, J. Phys. Chem. B, 2004, 108, 12181; DOI: https://doi.org/10.1021/jp040115f.
Ye. A. Arnautova, A. Jagielska, J. Pillardy, H. A. Scheraga, J. Phys. Chem. B, 2003, 107, 7143; DOI: https://doi.org/10.1021/jp0301498.
A. K. Al-Matar, H. Binous, J. Radioanal. Nucl. Chem., 2016, 310, 139; DOI: https://doi.org/10.1007/s10967-016-4814-5.
Ch. A. Gatsiou, C. S. Adjiman, C. C. Pantelides, Faraday Discuss., 2018, 211, 297; DOI: https://doi.org/10.1039/c8fd00064f.
R. F. W. Bader, Acc. Chem. Res., 1985, 18, 9; DOI: https://doi.org/10.1021/ar00109a003.
R. S. Mulliken, J. Chem. Phys., 1955, 23, 1841; DOI: https://doi.org/10.1063/1.1740589.
C. M. Breneman, K. B. Wiberg, J. Comput. Chem., 1990, 11, 361; DOI: https://doi.org/10.1002/jcc.540110311.
B. H. Besler, K. M. Merz, Jr., P. A. Kollman, J. Comput. Chem., 1990, 11, 431; DOI: https://doi.org/10.1002/jcc.540110404.
Ch. I. Bayly, P. Cieplak, W. D. Cornell, P. A. Kollman, J. Phys. Chem., 1993, 97, 10269; DOI: https://doi.org/10.1021/j100142a004.
H. Hu, Z. Lu, W. Yang, J. Chem. Theory Comput., 2007, 3, 1004; DOI: https://doi.org/10.1021/ct600295n.
D. E. Williams, R. R. Weller, J. Am. Chem. Soc., 1983, 105, 4143; DOI: https://doi.org/10.1021/ja00351a003.
P. G. Karamertzanis, C. C. Pantelides, Mol. Simul., 2004, 30, 413; DOI: https://doi.org/10.1080/08927020410001680769.
S. L. Mayo, B. D. Olafson, W. A. Goddard III, J. Phys. Chem., 1990, 94, 8897; DOI: https://doi.org/10.1021/j100389a010.
M. A. Neumann, J. Phys. Chem. B, 2008, 112, 9810; DOI: https://doi.org/10.1021/JP710575H/SUPPL_FILE/JP710575H-FILE003.PDF.
T. G. Cooper, K. E. Hejczyk, W. Jones, G. M. Day, J. Chem. Theory Comput., 2008, 4, 1795; DOI: https://doi.org/10.1021/ct800195g.
A. J. Stone, Chem. Phys. Lett., 1981, 83, 233; DOI: https://doi.org/10.1016/0009-2614(81)85452-8.
A. J. Stone, M. Alderton, Mol. Phys., 1985, 56, 1047; DOI: https://doi.org/10.1080/00268978500102891.
S. Brodersen, S. Wilke, F. J. J. Leusen, G. Engel, Phys. Chem. Chem. Phys., 2003, 5, 4923; DOI: https://doi.org/10.1039/b306396h.
A. V. Dzyabchenko, Russ. J. Phys. Chem. A, 2008, 82, 758; DOI: https://doi.org/10.1134/S0036024408050129.
A. D. Buckingham, P. W. Fowler, A. J. Stone, Int. Rev. Phys. Chem., 1986, 5, 107; DOI: https://doi.org/10.1080/01442358609353370.
G. M. Day, S. L. Price, M. Leslie, J. Phys. Chem. B, 2003, 107, 10919; DOI: https://doi.org/10.1021/jp035125f.
G. M. Day, S. L. Price, M. Leslie, Cryst. Growth Des., 2001, 1, 13; DOI: https://doi.org/10.1021/cg0055070.
D. J. Willock, S. L. Price, M. Leslie, C. R. A. Catlow, J. Comput. Chem., 1995, 16, 628; DOI: https://doi.org/10.1002/jcc.540160511.
S. L. Price, M. Leslie, G. W. A. Welch, M. Habgood, L. S. Price, P. G. Karamertzanis, G. M. Day, Phys. Chem. Chem. Phys., 2010, 12, 8478; DOI: https://doi.org/10.1039/c004164e.
P. G. Karamertzanis, S. L. Price, J. Chem. Theory Comput., 2006, 2, 1184; DOI: https://doi.org/10.1021/ct600111s.
M. U. Schmidt, U. Englert, J. Chem. Soc., Dalton Trans., 1996, 2077; DOI: https://doi.org/10.1039/dt9960002077.
M. U. Schmidt, H. Kalkhof, CRYSCA, Program for Crystal Structure Calculations of Flexible Molecules, Clariant GmbH, Frankfurt am Main, 1997.
D. E. Williams, Acta Crystallogr., Sect. A, 1996, 52, 326; DOI: https://doi.org/10.1107/S0108767395016679.
B. P. van Eijck, J. Kroon, J. Comput. Chem., 1999, 20, 799; DOI: https://doi.org/10.1002/(SICI)1096-987X(199906)20:8<799::AID-JCC6>3.0.CO;2-Z.
B. P. van Eijck, J. Kroon, Acta Crystallogr., Sect. B, 2000, 56, 535; DOI: https://doi.org/10.1107/S0108768100000276.
I. M. Sobol’, USSR Comput. Math. Math. Phys., 1967, 7, 86; DOI: https://doi.org/10.1016/0041-5553(67)90144-9.
R. G. Della Valle, E. Venuti, A. Brillante, A. Girlando, J. Chem. Phys., 2003, 118, 807; DOI: https://doi.org/10.1063/1.1527896.
P. G. Karamertzanis, C. C. Pantelides, J. Comput. Chem., 2005, 26, 304; DOI: https://doi.org/10.1002/jcc.20165.
A. Gavezzotti, J. Am. Chem. Soc., 1991, 113, 4622; DOI: https://doi.org/10.1021/ja00012a034.
D. W. M. Hofmann, T. Lengauer, Acta Crystallogr., Sect. A, 1997, 53, 225; DOI: https://doi.org/10.1107/S0108767396014353.
D. W. M. Hofmann, T. Lengauer, J. Mol. Struct., 1999, 474, 13; DOI: https://doi.org/10.1016/S0022-2860(98)00556-0.
A. V. Dzyabchenko, V. Agafonov, V. A. Davydov, J. Phys. Chem. A, 1999, 103, 2812; DOI: https://doi.org/10.1021/jp983951w.
V. K. Belsky, O. N. Zorkaya, P. M. Zorky, Acta Crystallogr., Sect. A, 1995, 51, 473; DOI: https://doi.org/10.1107/S0108767394013140.
T. Steiner, Acta Crystallogr., Sect. B, 2000, 56, 673; DOI: https://doi.org/10.1107/S0108768100002652.
A. J. Cruz Cabeza, E. Pidcock, G. M. Day, W. D. S. Motherwell, W. Jones, CrystEngComm, 2007, 9, 556; DOI: https://doi.org/10.1039/b702073b.
G. M. Day, W. D. S. Motherwell, H. L. Ammon, S. X. M. Boerrigter, R. G. Della Valle, E. Venuti, A. Dzyabchenko, J. D. Dunitz, B. Schweizer, B. P. van Eijck, P. Erk, J. C. Facelli, V. E. Bazterra, M. B. Ferraro, D. W. M. Hofmann, F. J. J. Leusen, C. Liang, C. C. Pantelides, P. G. Karamertzanis, S. L. Price, T. C. Lewis, H. Nowell, A. Torrisi, H. A. Scheraga, Y. A. Arnautova, M. U. Schmidt, P. Verwer, Acta Crystallogr., Sect. B, 2005, 61, 511; DOI: https://doi.org/10.1107/S0108768105016563.
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, A. Dzyabchenko, B. P. van Eijck, D. M. Elking, J. A. van den Ende, J. C. Facelli, M. B. Ferraro, L. Fusti-Molnar, Ch.-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, N. Marom, A. E. Masunov, P. McCabe, D. P. McMahon, H. Meekes, M. P. Metz, A. J. Misquitta, Sh. Mohamed, B. Monserrat, R. J. Needs, M. A. Neumann, J. Nyman, Sh. Obata, H. Oberhofer, A. R. Oganov, A. M. Orendt, G. I. Pagola, C. C. Pantelides, Ch. J. Pickard, R. Podeszwa, L. S. Price, S. L. Price, A. Pulido, M.G. Read, K. Reuter, E. Schneider, Ch. Schober, G. P. Shields, P. Singh, I. J. Sugden, K. Szalewicz, Ch. 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., Sect. B, 2016, 72, 439; DOI: https://doi.org/10.1107/S2052520616007447.
D. A. Bardwell, C. S. Adjiman, Ye. A. Arnautova, E. Bartashevich, S. X. M. Boerrigter, D. E. Braun, A. J. Cruz-Cabeza, G. M. Day, R. G. Della Valle, G. R. Desiraju, B. P. van Eijck, J. C. Facelli, M. B. Ferraro, D. Grillo, M. Habgood, D. W. M. Hofmann, F. Hofmann, K. V. J. Jose, P. G. Karamertzanis, A. V. Kazantsev, J. Kendrick, L. N. Kuleshova, F. J. J. Leusen, A. V. Maleev, A. J. Misquitta, Sh. Mohamed, R. J. Needs, M. A. Neumann, D. Nikylov, A. M. Orendt, R. Pal, C. C. Pantelides, Ch. J. Pickard, L. S. Price, S. L. Price, H. A. Scheraga, J. van den Streek, T. S. Thakur, S. Tiwari, E. Venuti, I. K. Zhitkov, Acta Crystallogr., Sect. B, 2011, 67, 535; DOI: https://doi.org/10.1107/S0108768111042868.
H. R. Karfunkel, F. J. J. Leusen, R. J. Gdanitz, J. Comput. Aided Mater. Des., 1994, 1, 177; DOI: https://doi.org/10.1007/BF00708708.
H. R. Karfunkel, R. J. Gdanitz, J. Comput. Chem., 1992, 13, 1171; DOI: https://doi.org/10.1002/jcc.540131002.
F. J. J. Leusen, Cryst. Growth Des., 2003, 3, 189; DOI: https://doi.org/10.1021/cg020034d.
I. D. H. Oswald, D. R. Allan, G. M. Day, W. D. S. Motherwell, S. Parsons, Cryst. Growth Des., 2005, 5, 1055; DOI: https://doi.org/10.1021/cg049647b.
J. Pillardy, C. Czaplewski, W. J. Wedemeyer, H. A. Scheraga, Helv. Chim. Acta, 2000, 83, 2214; DOI: https://doi.org/10.1002/1522-2675(20000906)83:9<2214::AID-HLCA2214>3.0.CO;2-E.
J. Pillardy, Ye. A. Arnautova, C. Czaplewski, K. D. Gibson, H. A. Scheraga, Proc. Natl. Acad. Sci. U. S. A., 2001, 98, 12351; DOI: https://doi.org/10.1073/pnas.231479298.
V. E. Bazterra, M. B. Ferraro, J. C. Facelli, J. Chem. Phys., 2002, 116, 5984; DOI: https://doi.org/10.1063/1.1458547.
V. E. Bazterra, M. B. Ferraro, J. C. Facelli, J. Chem. Phys., 2002, 116, 5992; DOI: https://doi.org/10.1063/1.1458548.
V. E. Bazterra, M. B. Ferraro, J. C. Facelli, Int. J. Quantum Chem., 2004, 96, 312; DOI: https://doi.org/10.1002/qua.10726.
O. Oña, V. E. Bazterra, M. C. Caputo, M. B. Ferraro, P. Fuentealba, J. C. Facelli, J. Mol. Struct. (THEOCHEM), 2004, 681, 149; DOI: https://doi.org/10.1016/j.theochem.2004.04.060.
V. E. Bazterra, M. Thorley, M. B. Ferraro, J. C. Facelli, J. Chem. Theory Comput., 2007, 3, 201; DOI: https://doi.org/10.1021/ct6002115.
A. R. Oganov, C. W. Glass, J. Chem. Phys., 2006, 124, 244704; DOI: https://doi.org/10.1063/1.2210932.
C. W. Glass, A. R. Oganov, N. Hansen, Comput. Phys. Commun., 2006, 175, 713; DOI: https://doi.org/10.1016/j.cpc.2006.07.020.
W. D. S. Motherwell, Mol. Cryst. Liq. Cryst., 2001, 356, 559; DOI: https://doi.org/10.1080/10587250108023734.
J. R. Holden, Z. Du, H. L. Ammon, J. Comput. Chem., 1993, 14, 422; DOI: https://doi.org/10.1002/jcc.540140406.
R. Martoňák, A. Laio, M. Bernasconi, C. Ceriani, P. Raiteri, F. Zipoli, M. Parrinello, Z. Kristallogr., 2005, 220, 489; DOI: https://doi.org/10.1524/zkri.220.5.489.65078.
H. Song, L. Vogt-Maranto, R. Wiscons, A. J. Matzger, M. E. Tuckerman, J. Phys. Chem. Lett., 2020, 11, 9751; DOI: https://doi.org/10.1021/acs.jpclett.0c02647.
D. H. Bowskill, I. J. Sugden, S. Konstantinopoulos, C. S. Adjiman, C. C. Pantelides, Annu. Rev. Chem. Biomol. Eng., 2021, 12, 593; DOI: https://doi.org/10.1146/annurev-chembioeng-060718-030256.
J. Wang, R. M. Wolf, J. W. Caldwell, P. A. Kollman, D. A. Case, J. Comput. Chem., 2004, 25, 1157; DOI: https://doi.org/10.1002/jcc.20035.
H. Sun, J. Phys. Chem. B, 1998, 102, 7338; DOI: https://doi.org/10.1021/jp980939v.
J. C. Osborn, P. York, J. Mol. Struct., 1999, 474, 43; DOI: https://doi.org/10.1016/S0022-2860(98)00558-4.
A. K. Rappé, C. J. Casewit, K. S. Colwell, W. A. Goddard III, W. M. Skiff, J. Am. Chem. Soc., 1992, 114, 10024; DOI: https://doi.org/10.1021/ja00051a040.
I. Jen Chen, D. Yin, A. D. MacKerell, J. Comput. Chem., 2002, 23, 199; DOI: https://doi.org/10.1002/jcc.1166.
W. L. Jorgensen, D. S. Maxwell, J. Tirado-Rives, J. Am. Chem. Soc., 1996, 118, 11225; DOI: https://doi.org/10.1021/ja9621760.
T. A. Halgren, J. Comput. Chem., 1996, 17, 490; DOI: https://doi.org/10.1002/(SICI)1096-987X(199604)17:5/6<490::AID-JCC1>3.0.CO;2-P.
G. M. Day, W. D. Sam Motherwell, W. Jones, Cryst. Growth Des., 2005, 5, 1023; DOI: https://doi.org/10.1021/cg049651n.
D. C. Sorescu, B. M. Rice, D. L. Thompson, J. Phys. Chem. A, 1998, 102, 8386; DOI: https://doi.org/10.1021/jp9820525.
D. C. Sorescu, B. M. Rice, D. L. Thompson, J. Phys. Chem. A, 1999, 103, 989; DOI: https://doi.org/10.1021/jp983847e.
S. W. Benson, J. H. Buss, J. Chem. Phys., 1958, 29, 546; DOI: https://doi.org/10.1063/1.1744539.
N. Cohen, S. W. Benson, Chem. Rev., 1993, 93, 2419; DOI: https://doi.org/10.1021/cr00023a005.
A. Smirnov, D. Lempert, T. Pivina, in Energetics Science and Technology in Central Europe (Center for [i>Energetic Concepts Development Series), Ed. R. W. Armstrong, Univ. of Maryland, College Park, 2012, p. 97.
P. R. Duchowicz, E. A. Castro, J. Arg. Chem. Soc., 2003, 91, No. 1–3, 29.
M. S. Westwell, M. S. Searle, D. J. Wales, D. H. Williams, J. Am. Chem. Soc., 1995, 117, 5013; DOI: https://doi.org/10.1021/ja00123a001.
D. V. Khakimov, T. S. Pivina, J. Phys. Chem. A, 2022, 126, 5207, DOI: https://doi.org/10.1021/acs.jpca.2c01114.
D. G. Piercey, D. E. Chavez, S. Heimsch, Ch. Kirst, T. M. Klapötke, J. Stierstorfer, Propellants, Explos. Pyrotech., 2015, 40, 491; DOI: https://doi.org/10.1002/prep.201400224.
T. M. Klapötke, D. G. Piercey, J. Stierstorfer, M. Weyrauther, Propellants, Explos. Pyrotech., 2012, 37, 527; DOI: https://doi.org/10.1002/prep.201100151.
P. Politzer, J. S. Murray, M. E. Edward Grice, M. Desalvo, E. Miller, Mol. Phys., 1997, 91, 923; DOI: https://doi.org/10.1080/002689797171030.
A. Hu, B. Larade, S. Dudiy, H. Abou-Rachid, L.-S. Lussier, H. Guo, Propellants, Explos. Pyrotech., 2007, 32, 331; DOI: https://doi.org/10.1002/prep.200700037.
H. J. Singh, M. K. Upadhyay, S. K. Sengupta, J. Mol. Model., 2014, 20, 2205; DOI: https://doi.org/10.1007/s00894-014-2205-9.
M. A. Suntsova, O. V. Dorofeeva, J. Mol. Graph. Model., 2017, 72, 220; DOI: https://doi.org/10.1016/j.jmgm.2017.01.013.
N. M. Baraboshkin, A.-M. Stratulat, T. S. Pivina, Russ. Chem. Bull., 2021, 70, 1893; DOI: https://doi.org/10.1007/s11172-021-3293-1.
N. V. Muravyev, K. A. Monogarov, I. N. Melnikov, A. N. Pivkina, V. G. Kiselev, Phys. Chem. Chem. Phys., 2021, 23, 15522; DOI: https://doi.org/10.1039/d1cp02201f.
A. F. Bedford, P. B. Edmondson, C. T. Mortimer, J. Chem. Soc., 1962, 2927; DOI: https://doi.org/10.1039/jr9620002927.
D. V. Khakimov, T. S. Pivina, Gorenie i vzryv [Com bus tion and Explosion], 2016, 9, No. 1, 118 (in Russian).
Yu. N. Matyushin, V. I. Pepekin, V. P. Lebedev, V. V. Chironov, L. M. Kostikova, Y. O. Inozemtsev, T. S. Pivina, A. B. Sheremetev, Proc. of the 30th Int. Ann. Conf. of the Fraunhofer ICT, Fraunhofer-Institut für Chemische Technologie, Pfinztal, 1999, p. 77.1.
C. Pan, M. P. Sampson, Y. Chai, R. H. Hauge, J. L. Margrave, J. Phys. Chem., 1991, 95, 2944; DOI: https://doi.org/10.1021/j100161a003.
E. Scrocco, J. Tomasi, Adv. Quantum Chem., 1978, 11, 115; DOI: https://doi.org/10.1016/S0065-3276(08)60236-1.
V. P. Zelenov, N. M. Baraboshkin, D. V. Khakimov, N. V. Muravyev, D. B. Meerov, I. A. Troyan, T. S. Pivina, A. V. Dzyabchenko, I. V. Fedyanin, Cryst EngComm, 2020, 22, 4823; DOI: https://doi.org/10.1039/d0ce00639d.
R. A. Sayle, E. J. Milner-White, Trends Biochem. Sci., 1995, 20, 374; DOI: https://doi.org/10.1016/S0968-0004(00)89080-5.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, D. J. Fox, Gaussian 09 Rev. D.01, Gaussian, Inc., Wallingford CT, 2016.
D. E. Williams, Acta Crystallogr., Sect. A, 1971, 27, 452; DOI: https://doi.org/10.1107/S0567739471000998.
F. Bertaut, J. Phys. le Radium, 1952, 13, 499; DOI: https://doi.org/10.1051/jphysrad:019520013011049900.
A. Dzyabchenko, H. A. Scheraga, Acta Crystallogr., Sect. B, 2004, 60, 228; DOI: https://doi.org/10.1107/S010876810400312X.
A. V. Dzyabchenko, Sov. Phys. Crystallogr., 1983, 28.
R. Fletcher, Fortran Subroutines for Minimization by Quasi-Newton Methods, Tech. Rpt. AERE-R7125, Atomic Energy Res. Est., Harwell, 1972.
A. V. Dzyabchenko, Acta Crystallogr., Sect. B, 1994, 50, 414; DOI: https://doi.org/10.1107/S0108768193013552.
M. R. Nyden, G. A. Petersson, J. Chem. Phys., 1981, 75, 1843; DOI: https://doi.org/10.1063/1.442208.
M. A. Suntsova, O. V. Dorofeeva, J. Chem. Eng. Data, 2014, 59, 2813; DOI: https://doi.org/10.1021/je500440y.
M. A. Suntsova, O. V. Dorofeeva, J. Chem. Eng. Data, 2016, 61, 313; DOI: https://doi.org/10.1021/acs.jced.5b00558.
M. J. Kamlet, S. J. Jacobs, J. Chem. Phys., 1968, 48, 23; DOI: https://doi.org/10.1063/1.1667908.
L. M. Foroughi, A. J. Matzger, Cryst. Growth Des., 2021, 21, 5873; DOI: https://doi.org/10.1021/acs.cgd.1c00746.
L. Hu, R. J. Staples, J. M. Shreeve, Chem. Eng. J., 2021, 420, 129839; DOI: https://doi.org/10.1016/J.CEJ.2021.129839.
N. Liu, B. Duan, X. Lu, Q. Zhang, M. Xu, H. Mo, B. Wang, CrystEngComm, 2019, 21, 7271; DOI: https://doi.org/10.1039/c9ce01221d.
K. B. Landenberger, O. Bolton, A. J. Matzger, J. Am. Chem. Soc., 2015, 137, 5074; DOI: https://doi.org/10.1021/jacs.5b00661.
J. Zhang, J. M. Shreeve, CrystEngComm, 2016, 18, 6124; DOI: https://doi.org/10.1039/c6ce01239f.
N. M. Baraboshkin, I. D. Nesterov, T. S. Pivina, Gorenie i vzryv [Combustion and Explosion], 2020, 13, No. 3, 129; DOI: https://doi.org/10.30826/ce20130313 (in Russian).
H. H. Cady, A. C. Larson, D. T. Cromer, Acta Crystallogr., 1966, 20, 336; DOI: https://doi.org/10.1107/s0365110x6600080x.
A. S. Bailey, J. R. Case, Tetrahedron, 1958, 3, 113; DOI: https://doi.org/10.1016/0040-4020(58)80003-4.
A. S. Bailey, R. J. P. Williams, J. D. Wright, J. Chem. Soc., 1965, 2579; DOI: https://doi.org/10.1039/JR9650002579.
H. Zhang, C. Guo, X. Wang, J. Xu, X. He, Y. Liu, X. Liu, H. Huang, J. Sun, Cryst. Growth Des., 2013, 13, 679; DOI: https://doi.org/10.1021/cg301353f.
Z. Yang, H. Li, X. Zhou, C. Zhang, H. Huang, J. Li, F. Nie, Cryst. Growth Des., 2012, 12, 5155; DOI: https://doi.org/10.1021/cg300955q.
L. M. Foroughi, R. A. Wiscons, D. R. Du Bois, A. J. Matzger, Chem. Commun., 2020, 56, 2111; DOI: https://doi.org/10.1039/c9cc09465b.
N. M. Baraboshkin, V. P. Zelenov, M. E. Minyaev, T. S. Pivina, CrystEngComm, 2022, 24, 235; DOI: https://doi.org/10.1039/d1ce00977j.
N. M. Baraboshkin, D. V. Khakimov, V. P. Zelenov, A. S. Smirnov, T. S. Pivina, Gorenie i vzryv [Combustion and Explosion], 2021, 14, No. 4, 104; DOI: https://doi.org/10.30826/ce21140411 (in Russian).
S. Tsuzuki, K. Honda, T. Uchimaru, M. Mikami, J. Chem. Phys., 2006, 125, 124304; DOI: https://doi.org/10.1063/1.2354495.
Z. Yang, Y. Wang, J. Zhou, H. Li, H. Huang, F. Nie, Propellants, Explos. Pyrotech., 2014, 39, 9; DOI: https://doi.org/10.1002/prep.201300086.
X. Wei, Y. Ma, X. Long, C. Zhang, CrystEngComm, 2015, 17, 7150; DOI: https://doi.org/10.1039/c5ce01355k.
N. M. Baraboshkin, V. P. Zelenov, A. V. Dzyabchenko, I. V. Fedyanin, T. S. Pivina, J. Mol. Struct., 2019, 1190, 135; DOI: https://doi.org/10.1016/j.molstruc.2019.04.037.
A. S. Zharkov, P. I. Kalmykov, Yu. N. Burtsev, N. P. Kuznetsova, I. A. Merzhanov, N. V. Chukanov, V. V. Zakharov, G. V. Romanenko, K. A. Sidorov, V. E. Zarko, Russ. Chem. Bull., 2014, 63, 1785; DOI: https://doi.org/10.1007/s11172-014-0668-6.
A. M. Churakov, S. L. loffe, V. A. Tartakovsky, Mendeleev Commun., 1995, 6, 227; DOI: https://doi.org/10.1070/MC1995v005n06ABEH000539.
V. P. Zelenov, A. A. Lobanova, S. V. Sysolyatin, N. V. Sevodina, Russ. J. Org. Chem., 2013, 49, 455; DOI: https://doi.org/10.1134/S107042801303024X.
V. A. Teselkin, Combust. Explos. Shock Waves, 2009, 45, 632; DOI: https://doi.org/10.1007/s10573-009-0076-7.
V. G. Kiselev, N. P. Gritsan, V. E. Zarko, P. I. Kalmykov, V. A. Shandakov, Combust. Explos. Shock Waves, 2007, 43, 562; DOI: https://doi.org/10.1007/s10573-007-0074-6.
N. M. Baraboshkin, D. V. Khakimov, T. S. Pivina, Russ. Chem. Bull., 2022, 71, 38; DOI: https://doi.org/10.1007/s11172-022-3373-x.
V. I. Pepekin, Russ. J. Phys. Chem. B, 2010, 4, 954; DOI: https://doi.org/10.1134/s1990793110060138.
V. I. Pepekin, Yu. N. Matyushin, T. V. Gubina, Russ. J. Phys. Chem. B, 2011, 5, 97; DOI: https://doi.org/10.1134/S1990793111020102.
Y. Ma, A. Zhang, X. Xue, D. Jiang, Y. Zhu, C. Zhang, Cryst. Growth Des., 2014, 14, 6101; DOI: https://doi.org/10.1021/cg501267f.
M. A. Spackman, D. Jayatilaka, CrystEngComm, 2009, 11, 19; DOI: https://doi.org/10.1039/b818330a.
A. Smirnov, D. Lempert, T. Pivina, D. Khakimov, Cent. Eur. J. Energ. Mater., 2011, 8, 233.
Recommendations on Transportation of Dangerous Cargoes. Management and Criteria of Tests (ST/SG/AC.10/11/Rev. 4), United Nations, New York–Geneva, 4th ed., 2003, 120 pp.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Animal Testing and Ethics
No human or animal subjects were used in this research.
Conflict of Interest
The authors declare no competing interests.
Additional information
Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 70th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 73, No. 2, pp. 243–282, February, 2024.
Rights and permissions
About this article
Cite this article
Baraboshkin, N.M., Zelenov, V.P., Khakimov, D.V. et al. Cocrystals of polynitrogen compounds as a basis for promising energetic materials: crystal structure prediction methods, their experimental verification, and evaluation of cocrystal properties. Russ Chem Bull 73, 243–282 (2024). https://doi.org/10.1007/s11172-024-4137-6
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-024-4137-6