Hirshfeld surface analysis has been widely used in recent years as a means to quantify and visualize various types of intermolecular interactions in molecular crystals. This review article introduces intermolecular interactions discussed with Hirshfeld surface analysis and 2D fingerprint plots. In addition, using CIF files obtained from our previous results, Hirshfeld surface analysis was newly performed, and the resulting 3DHirshfeld surfaces, 2D print plots, molecular structural features, and crystal structure relationships were described. Classification of their intermolecular interactions, statistical discussion focused on crystalline water and perspective on ligand-protein docking are also mentioned.
KeywordsChemical CrystallographyCambridge Structure DatabaseCIFHirshfeld Surface AnalysisSchiff Base
Zeng, W., Wang, X., Zhou, T. and Zhang, Y. (2023) Crystal Structure, Photophysical Study, Hirshfeld Surface Analysis, and Nonlinear Optical Properties of a New Hydroxyphenylamino Meldrum’s Acid Derivative. Molecules, 28, Article No. 2181. https://doi.org/10.3390/molecules28052181
Kumar, M., Jaiswar, G., Afzal, M., Muddassir, M., Alarifi, A., Fatima, A., Siddiqui, N., Ayub, R., Abduh, N.A.Y., Saeed, W.S. and Javed, S. (2023) Quantum Computational, Spectroscopic (FT-IR, FT-Raman, NMR, and UV-Vis) Hirshfeld Surface and Molecular Docking-Dynamics Studies on 5-Hydroxymethyluracil (Monomer and Trimer). Molecules, 28, Article No. 2116. https://doi.org/10.3390/molecules28052116
Semenova, L.I., Ling, I. and Sobolev, A.N. (2023) Chirality as a Feature of the Crystal Structure of Lanthanide Ion Complexes—Some Simple Examples. Crystals, 13, Article No. 337. https://doi.org/10.3390/cryst13020337
Bojarska, J., Breza, M., Remko, M., Czyz, M., Gajos-Michniewicz, A., Zimecki, M., Kaczmarek, K., Madura, I.D., Wojciechowski, J.M. and Wolf, W.M. (2022) Structural and Biofunctional Insights into the Cyclo(Pro-Pro-Phe-Phe-) Scaffold from Experimental and in Silico Studies: Melanoma and Beyond. International Journal of Molecular Sciences, 23, Article No. 7173. https://doi.org/10.3390/ijms23137173
Craciun, N., Chisca, D., Melnic, E. and Fonari, M.S. (2023) Unprecedented Coordination Compounds with 4,4’-Diaminodiphenylethane as a Supramolecular Agent and Ditopic Ligand: Synthesis, Crystal Structures and Hirshfeld Surface Analysis. Crystals, 13, Article No. 289. https://doi.org/10.3390/cryst13020289
Deeloed, W., Wannapaiboon, S., Pansiri, P., Kumpeerakij, P., Phomphrai, K., Laobuthee, A., Hanlumyuang, Y., Suramitr, S., Pinyou, P. and Wattanathana, W. (2020) Crystal Structure and Hirshfeld Surface Analysis of Bis(Triethanolamine)Nickel(II) Dinitrate Complex and a Revelation of Its Characteristics via Spectroscopic, Electrochemical and DFT Studies towards a Promising Precursor for Metal Oxides Synthesis. Crystals, 10, Article No. 474. https://doi.org/10.3390/cryst10060474
Gacki, M., Kafarska, K., Pietrzak, A., Korona-Głowniak, I. and Wolf, W.M. (2020) Quasi-Isostructural Co(II) and Ni(II) Complexes with Mefenamato Ligand: Synthesis, Characterization, and Biological Activity. Molecules, 25, Article No. 3099. https://doi.org/10.3390/molecules25133099
Krupka, K.M., Banach, S., Pocheć, M., Panek, J.J. and Jezierska, A. (2023) Making and Breaking—Insight into the Symmetry of Salen Analogues. Symmetry, 15, Article No. 424. https://doi.org/10.3390/sym15020424
Mahmoudi, G., Kumar Seth, S., Bauza Riera, A., Ivanovich Zubkov, F. and Frontera, A. (2020) Novel Pb(II) Complexes: X-Ray Structures, Hirshfeld Surface Analysis and DFT Calculations. Crystals, 10, Article No. 568. https://doi.org/10.3390/cryst10070568
Noor, A. (2022) Crystallographic Evidence of η1-Coordination of Bulky Aminopyridine in Halide-Containing Iron(II) Complexes. Crystals, 12, Article No. 697. https://doi.org/10.3390/cryst12050697
Masternak, J., Zienkiewicz-Machnik, M., Łakomska, I., Hodorowicz, M., Kazimierczuk, K., Nosek, M., Majkowska-Młynarczyk, A., Wietrzyk, J. and Barszcz, B. (2021) Synthesis and Structure of Novel Copper(II) Complexes with N,O-or N,N-Donors as Radical Scavengers and a Functional Model of the Active Sites in Metalloenzymes. International Journal of Molecular Sciences, 22, Article No. 7286. https://doi.org/10.3390/ijms22147286
Altowyan, M.S., Haukka, M., Soliman, S.M., Barakat, A., Alaswad, S.O., Boraei, A.T.A., Gad, E.M. and Youssef, M.F. (2023) Synthesis, Characterization and Single Crystal X-Ray Diffraction Analysis of Fused Triazolo/Thiadiazole Clubbed with Indole Scaffold. Crystals, 13, Article No. 423. https://doi.org/10.3390/cryst13030423
Ghazzy, A., Taher, D., Korb, M., Al Khalyfeh, K., Helal, W., Amarne, H., Rüffer, T., Ishtaiwi, Z. and Lang, H. (2022) Rearrangement of Diferrocenyl 3,4-Thiophene Dicarboxylate. Inorganics, 10, Article No. 96. https://doi.org/10.3390/inorganics10070096
Altowyan, M.S., Khalil, S.M.S.M., Al-Wahaib, D., Barakat, A., Soliman, S.M., Ali, A.E. and Elbadawy, H.A. (2022) Synthesis of a Novel Unexpected Cu(II)-Thiazolidine Complex—X-Ray Structure, Hirshfeld Surface Analysis, and Biological Studies. Molecules, 27, Article No. 4583. https://doi.org/10.3390/molecules27144583
Seth, S.K. (2018) The Importance of CH···X (X=O, π) Interaction of a New Mixed Ligand Cu(II) Coordination Polymer: Structure, Hirshfeld Surface and Theoretical Studies. Crystals, 8, Article No. 455. https://doi.org/10.3390/cryst8120455
Baykov, S.V., Mikherdov, A.S., Novikov, A.S., Geyl, K.K., Tarasenko, M.V., Gureev, M.A. and Boyarskiy, V.P. (2021) π-π Noncovalent Interaction Involving 1,2,4-and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study. Molecules, 26, Article No. 5672. https://doi.org/10.3390/molecules26185672
Jmai, M., Gatfaoui, S., Issaoui, N., Roisnel, T., Kazachenko, A.S., Al-Dossary, O., Marouani, H. and Kazachenko, A.S. (2023) Synthesis, Empirical and Theoretical Investigations on New Histaminium Bis(Trioxonitrate) Compound. Molecules, 28, Article No. 1931. https://doi.org/10.3390/molecules28041931
Zamisa, S.J. and Omondi, B. (2022) Microwave Assisted Synthesis, Crystal Structure and Hirshfeld Surface Analysis of Some 2-Formimidate-3-Carbonitrile Derivatives Bearing 4H-Pyran and Dihydropyridine Moieties. Molbank, 2022, M1364. https://doi.org/10.3390/M1364
Sukhikh, A., Klyamer, D., Bonegardt, D. and Basova, T. (2023) Octafluoro-Substituted Phthalocyanines of Zinc, Cobalt, and Vanadyl: Single Crystal Structure, Spectral Study and Oriented Thin Films. International Journal of Molecular Sciences, 24, Article No. 2034. https://doi.org/10.3390/ijms24032034
Novoa-Ramírez, C.S., Silva-Becerril, A., Olivera-Venturo, F.L., García-Ramos, J.C., Flores-Alamo, M. and Ruiz-Azuara, L. (2020) N/N Bridge Type and Substituent Effects on Chemical and Crystallographic Properties of Schiff-Base (Salen/Salphen) Niii Complexes. Crystals, 10, Article No. 616. https://doi.org/10.3390/cryst10070616
Asad, M., Arshad, M.N., T.N., M.M. and Asiri, A.M. (2022) Chitosan Catalyzed Novel Piperidinium Dicoumarol: Green Synthesis, X-Ray Diffraction, Hirshfeld Surface and DFT Studies. Polymers, 14, Article No. 1854. https://doi.org/10.3390/polym14091854
Minaeva, V., Karaush-Karmazin, N., Panchenko, O., Minaev, B. and Ågren, H. (2023) Hirshfeld and AIM Analysis of the Methylone Hydrochloride Crystal Structure and Its Impact on the IR Spectrum Combined with DFT Study. Crystals, 13, Article No. 383. https://doi.org/10.3390/cryst13030383
Ruelas-álvarez, G.Y., Cárde-nas-Valenzuela, A.J., Galaviz-Moreno, L.L., Cruz-Enríquez, A., Campos-Gaxiola, J.J., Höpfl, H., Baldenebro-López, J., Vargas-Olvera, E.C., Miranda-Soto, V., García Grajeda, B.A. and Glossman-Mitnik, D. (2022) Four-Coordinate Monoboron Complexes with 8-Hydroxyquinolin-5-Sulfonate: Synthesis, Crystal Structures, Theoretical Studies, and Luminescence Properties. Crystals, 12, Article No. 783. https://doi.org/10.3390/cryst12060783
Zięba, S., Piotrowska, A., Mizera, A., Ławniczak, P., Markiewicz, K.H., Gzella, A., Dubis, A.T. and Łapiński, A. (2021) Spectroscopic and Structural Study of a New Conducting Pyrazolium Salt. Molecules, 26, Article No. 4657. https://doi.org/10.3390/molecules26154657
Zhuang, T.-H., Lin, Y.-M., Lin, H.-W., Guo, Y.-L., Li, Z.-W., Du, K.-Z., Wang, Z.-P. and Huang, X.-Y. (2023) Luminescence Enhancement and Temperature Sensing Properties of Hybrid Bismuth Halides Achieved via Tuning Organic Cations. Molecules, 28, Article No. 2380. https://doi.org/10.3390/molecules28052380
Smarun, A.V., Jevtovic, V. and Ganguly, R. (2020) Synthesis, Structure and Hirshfeld Surface Analysis of Phosphine-Imidazolium Salt. Molbank, 2020, M1141. https://doi.org/10.3390/M1141
Daśko, M., Dołęga, A., Siedzielnik, M., Biernacki, K., Ciupak, O., Rachon, J. and Demkowicz, S. (2021) Novel 1,2,3-Triazole Derivatives as Mimics of Steroidal System—Synthesis, Crystal Structures Determination, Hirshfeld Surfaces Analysis and Molecular Docking. Molecules, 26, Article No. 4059. https://doi.org/10.3390/molecules26134059
Vassilyeva, O.Y., Buvaylo, E.A., Nesterova, O.V., Sobolev, A.N. and Nesterov, D.S. (2023) New Low-Dimensional Organic-Inorganic Lead Halide Hybrid Systems Directed by Imidazo[1,5-a]pyridinium-Based Cation or Imines: Synthesis, Structures, Non-Covalent Interactions and Optical Properties. Crystals, 13, Article No. 307. https://doi.org/10.3390/cryst13020307
Boraei, A.T.A., Soliman, S.M., Haukka, M., El Tamany, E.S.H., Al-Majid, A.M. and Barakat, A. (2021) X-Ray Single Crystal Structure, Tautomerism Aspect, DFT, NBO, and Hirshfeld Surface Analysis of a New Schiff Bases Based on 4-Amino-5-Indol-2-yl-1,2,4-Triazole-3-Thione Hybrid. Crystals, 11, Article No. 1041. https://doi.org/10.3390/cryst11091041
Collart, A., Zeller, M. and Hillesheim, P.C. (2022) Surface and Void Space Analysis of the Crystal Structures of Two Lithium Bis(pentafluoroethanesulfonyl)imide Salts. Crystals, 12, Article No. 701. https://doi.org/10.3390/cryst12050701
Hamlaoui, M., Hamlaoui, I., Damous, M., Belhocine, Y., Sbei, N., Ali, F.A.M., Alghamdi, M.A., Talab, S., Rahali, S. and Merazig, H. (2022) Synthesis of Two Novel Copper(II) Complexes as Potential Inhibitors of HIV-1 Protease Enzyme: Experimental and Theoretical Investigations. Crystals, 12, Article No. 1066. https://doi.org/10.3390/cryst12081066
Shivanna, C., Patil, S.M., Mallikarjunaswamy, C., Ramu, R., Akhileshwari, P., Nagaraju, L.R., Sridhar, M.A., Khanum, S.A., Ranganatha, V.L., Silina, E., Stupin, V. and Achar, R.R. (2022) Synthesis, Characterization, Hirshfeld Surface Analysis, Crystal Structure and Molecular Model-ing Studies of 1-(4-(Methoxy(phenyl)methyl)-2-methylphenoxy)butan-2-one Derivative as a Novel α-Glucosidase Inhibitor. Crystals, 12, Article No. 960. https://doi.org/10.3390/cryst12070960
Osman, D.A., Macías, M.A., Al-Wahaibi, L.H., Al-Shaalan, N.H., Zondagh, L.S., Joubert, J., Garcia-Granda, S. and El-Emam, A.A. (2021) Structural Insights and Docking Analysis of Adamantane-Linked 1,2,4-Triazole Derivatives as Potential 11β-HSD1 Inhibitors. Molecules, 26, Article No. 5335. https://doi.org/10.3390/molecules26175335
Abou-Taleb, H.A., Shoman, M.E., Makram, T.S., Abdel-Aleem, J.A. and Abdelkader, H. (2023) Exploration of the Safety and Solubilization, Dissolution, Analgesic Effects of Common Basic Excipients on the NSAID Drug Ketoprofen. Pharmaceutics, 15, Article No. 713. https://doi.org/10.3390/pharmaceutics15020713
Moyano, S., Diosdado, B., San Felices, L., Elduque, A. and Giménez, R. (2021) Structural Diversity of Hydrogen-Bonded 4-Aryl-3,5-Dimethylpyrazoles for Supramolecular Materials. Materials, 14, Article No. 4550. https://doi.org/10.3390/ma14164550
Wattanathana, W., Suetrong, N., Kongsamai, P., Chansaenpak, K., Chuanopparat, N., Hanlumyuang, Y., Kanjanaboos, P. and Wannapaiboon, S. (2021) Crystallographic and Spectroscopic Investigations on Oxidative Coordination in the Heteroleptic Mononuclear Complex of Cerium and Benzoxazine Dimer. Molecules, 26, Article No. 5410. https://doi.org/10.3390/molecules26175410
Zhou, M.-M. and Xiang, D. (2022) Theoretical Prediction of Structures and Properties of 2,4,6-Trinitro-1,3,5-Triazine (TNTA) Green Energetic Materials from DFT and ReaxFF Molecular Modeling. Materials, 15, Article No. 3873. https://doi.org/10.3390/ma15113873
Standish, K., Zeller, M., Barbosa, A.J. and Hillesheim, P.C. (2022) Examining the Non-Covalent Interactions for Two Polymorphs of a 2,1,3-benzoxadiazole Derivative. Crystals, 12, Article No. 1143. https://doi.org/10.3390/cryst12081143
Rayes, A., Zárate-Roldán, S., Ara, I., Moncer, M., Dege, N., Gimeno, M.C., Ayed, B. and Herrera, R.P. (2021) Single-Crystal-to-Single-Crystal Transformation and Catalytic Properties of New Hybrid Perhalidometallates. Catalysts, 11, Article No. 758. https://doi.org/10.3390/catal11070758
Psycharis, V., Dermitzaki, D. and Raptopoulou, C.P. (2021) The Use of Hirshfeld Surface Analysis Tools to Study the Intermolecular Interactions in Single Molecule Magnets. Crystals, 11, Article No. 1246. https://doi.org/10.3390/cryst11101246
Spackman, M.A. and Jayatilaka, D. (2009) Hirshfeld Surface Analysis. CrystEngComm, 11, 19-32. https://doi.org/10.1039/B818330A
Carey, J.R., Ma, S.K., Pfister, T.D., Garner, D.K., Kim, H.K., Abramite, J.A., Wang, Z., Guo, Z. and Lu, Y. (2004) A Site-Selective Dual Anchoring Strategy for Artificial Metalloprotein Design. Journal of the American Chemical Society, 126, 10812-10813. https://doi.org/10.1021/ja046908x
Matsuo, T., Imai, C., Yoshida, T., Saito, T., Hayashi, T. and Hirota, S. (2012) Creation of an Artificial Metalloprotein with a Hoveyda-Grubbs Catalyst Moiety through the Intrinsic Inhibition Mechanism of α-Chymotrypsin. Chemical Communications, 48, 1662-1664. https://doi.org/10.1039/c2cc16898g
Maglio, O., Nastri, F. and Lombardi, A. (2012) Structural and Functional Aspects of Metal Binding Sites in Natural and Designed Metalloproteins. Ionic Interactions in Natural and Synthetic Macromolecules, 11, 361-450. https://doi.org/10.1002/9781118165850.ch11
Jelsch, C., Ejsmont, K. and Huder, L. (2014) The Enrichment Ratio of Atomic Contacts in Crystals, an Indicator Derived from the Hirshfeld Surface Analysis. IUCrJ, 1, 119-128. https://doi.org/10.1107/S2052252514003327
Ward, S.C. and Sadiq, G. (2020) Introduction to the Cambridge Structural Database—A Wealth of Knowledge Gained from a Million Structures. CrystEngComm, 22, 7143-7144. https://doi.org/10.1039/D0CE90154G
Turner, M.J., Mckinnon, J.J., Wolff, S.K., Grimwood, D.J., Spackman, P.R., Jayatilaka, D. and Spackman, M.A. (2017) CrystalExplorer17. University of Western Australia, Perth.
Suda, S., Akitsu, T., Onami, Y. and Haraguchi, T. (2021) Orthorhombic Polymorphism of 4-(2-Phenyldiazenyl)-2-[(phenylimino)methyl]phenol. X-Ray Structure Analysis Online, 37, 17-18. https://doi.org/10.2116/xraystruct.37.17
Noor, S., Suda, S., Haraguchi, T., Khatoon, F. and Akitsu, T. (2021) Chiral Crystallization of a Zinc(II) Complex. Acta Crystallographica Section E, 77, 542-546. https://doi.org/10.1107/S2056989021003650
Akitsu, T., Suda, S. and Katsuumi, N. (2021) Beyond the Scope of Each Computational Chemistry. Edelweiss Chemical Science Journal, 4, 25-26. https://doi.org/10.33805/2641-7383.128
Onami, Y., Siddaraju, B.P., Anilkumar, H.G., Yathirajan, H.S., Haraguchi, T. and Akitsu, T. (2019) (Z)-1-Benzoyl-5-benzylidene-2-hydroxy-4-oxo-4,5-dihydro-1H-pyrrole-3-carbonitrile. IUCrData, 4, x190220. https://doi.org/10.1107/S2414314619002207
Numata, T., Ikenomoto, S. and Akitsu, T. (2016) 4,4’-(1,2-Diazaniumylethane-1,2-diyl) dibenzoate trihydrate. IUCrData, 1, x160252. https://doi.org/10.1107/S2414314616002522
Aritake, Y., Watanabe, Y. and Akitsu, T. (2010) 4-Phenyldiazenyl-2-[(R)-(1-phenylethyl) iminomethyl]phenol. Acta Crystallographica Section E, 66, o749. https://doi.org/10.1107/S1600536810007762
Moriwaki, R., Yagi, S., Haraguchi, T. and Akitsu, T. (2017) 6-[(R)-(2-Hydroxy-1-phenylethyl)aminomethylidene]-4-(2-phenyldiazen-1-yl)cyclohexa-2,4-dien-1-one. IU-CrData, 2, x170979. https://doi.org/10.1107/S2414314617009798
Akitsu, T. and Einaga, Y. (2006) A Chiral Photochromic Schiff Base: (R)-4-bromo-2-[(1-phenylethyl)iminomethyl]phenol. Acta Crystallographica Section E, 62, o4315-o4317. https://doi.org/10.1107/S1600536806034891
Miura, Y., Aritake, Y. and Akitsu, T. (2009) A Chiral Photochromic Schiff Base: (R)-4-methoxy-2-[(1-phenylethyl)iminomethyl]phenol. Acta Crystallographica Section E, 65, o2381. https://doi.org/10.1107/S1600536809035557
Akitsu, T. and Einaga, Y. (2003) A Redetermination of bis(N-methylethylenediamine-κ2N,N’)bis(perchlorato-κO)copper(II). Acta Crystallographica Section E, 59, m991-m993. https://doi.org/10.1107/S160053680302213X
Akitsu, T. and Einaga, Y. (2004) Bis(5-chloro-N-isopropylsalicyldenaminato-κ2N,O) copper(II). Acta Crystallographica Section E, 60, m436-m438. https://doi.org/10.1107/S1600536804005938
Akitsu, T. and Einaga, Y. (2004) Bis(N-ethyl-ethylenediamine-κ2N,N’)copper(II)-hexa-cyano-cobaltate(III)-water (3/2/4): A Two-Dimensional Ladder Structure of a Bimetallic Assembly. Acta Crystallographica Section E, 62, m750-m752. https://doi.org/10.1107/S1600536806008105
Yagi, S., Haraguchi, T. and Akitsu, T. (2004) Crystal Structure of (E)-3-[(2,6-dimethylphenyl) diazenyl]-7-methyl-1H-indazole. Acta Crystallographica Section E, 74, m1421-m1423. https://doi.org/10.1107/S2056989018012483
Moriwaki, R. and Akitsu, T. (2015) Crystal Structure of 2-{(R)-[1-(4-bromophenyl) ethyl]iminomethyl}-4-(phenyldiazenyl)phenol, a Chiral Photochromic Schiff Base. Acta Crystallographica Section E, 71, o886-o887. https://doi.org/10.1107/S2056989015019866
Yamazaki, S., Nishiyama, K., Yagi, S., Haraguchi, T. and Akitsu, T. (2018) Crystal Structure of 3,6-Dihydroxy-4,5-dimethylbenzene-1,2-dicarbaldehyde. Acta Crystallographica Section E, 74, 1424-1426. https://doi.org/10.1107/S2056989018012495
Moon, D., Takase, M., Akitsu, T. and Choi, J.-H. (2017) Crystal Structure of Bis[cis-(1,4,8,11-tetraazacyclotetradecane-κ4N)bis(thiocyanato-κN)chromium(III)] Dichromate Monohydrate from Synchrotron X-Ray Diffraction Data. Acta Crystallographica Section E, 73, 72-75. https://doi.org/10.1107/S2056989016020120
Moon, D., Tanaka, S., Akitsu, T. and Choi, J.-H. (2015) Crystal Structure of Hexakis(urea-κO)chromium(III) Dichromate Bromide Monohydrate from Synchrotron X-Ray Data. Acta Crystallographica Section E, 71, 1336-1339. https://doi.org/10.1107/S2056989015019258
Akitsu, T., Takeuchi, Y. and Einaga, Y. (2004) Racemic 3,5-Dichloro-2-{[(1-phenylethyl) imino]methyl}phenol. Acta Crystallographica Section C, 60, o801-o802. https://doi.org/10.1107/S0108270104017354
Mahesha, N., Yathirajan, H.S., Furuya, T., Akitsu, T. and Glidewell, C. (2019) The Crystal Structure of 1-(2-Iodobenzoyl)-4-(pyrimidin-2-yl)piperazine: A Three-Dimensional Hydrogen-Bonded Framework, Augmented by π-π Stacking Interactions and I···N Halogen Bonds. Acta Crystallographica Section E, 75, 129-133. https://doi.org/10.1107/S205698901801811X
Akitsu, T. and Einaga, Y. (2005) trans-Bis(2,2-diphenylethylamine-κN)bis(5,5-diphenylhydantoina-to-κN3)copper(II) and Its Chloroform Disolvate. Acta Crystallographica Section C, 61, m183-m186. https://doi.org/10.1107/S010827010500209X
Akitsu, T. and Einaga, Y. (2004) trans-Bis(5,5-diphenylhydantoinato)bis(2-phenylethyla-mine)copper(II). Acta Crystallographica Section E, 50, m524-m526. https://doi.org/10.1107/S1600536804007378
Baldi, P. and Hornik, K. (1989) Neural Networks and Principal Component Analysis: Learning from Examples without Local Minima. Neural Networks, 2, 53-58. https://doi.org/10.1016/0893-6080(89)90014-2
Katsuumi, N., Onami, Y., Pradhan, S., Haraguchi, T. and Akitsu, T. (2020) Crystal Structure and Hirshfeld Sur-face Analysis of (aqua-κO)(methanol-κO)[N-(2-oxido-benzylidene)-threoninato-κ3O,N,O’]copper(II). Acta Crystallographica Section E, 76, 1539-1542. https://doi.org/10.1107/S2056989020011706
Furuya, T., Nakane, D., Kitanishi, K., Katsuumi, N., Tsaturyan, A., Shcherbakov, I. N., Unno, M. and Akitsu, T. (2023) A Novel Hybrid Protein Composed of Superoxide-Dismutase-Active Cu(II) Complex and Lysozyme. Scientific Reports, 13, Article No. 6892. https://doi.org/10.1038/s41598-023-33926-1
Akitsu, T., Kuroda, Y., Suda, S., Furuya, T., Haraguchi, T. and Unno, M. (2021) Weakly Non-Covalent Docking of Amino-Acid Schiff Base Zn(II) Complex to Lysozyme. Key Engineering Materials, 888, 105-110. https://doi.org/10.4028/www.scientific.net/KEM.888.105