{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,15]],"date-time":"2026-10-15T10:05:11Z","timestamp":1792058711612,"version":"4.4.0"},"reference-count":89,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2026,3,21]],"date-time":"2026-03-21T00:00:00Z","timestamp":1774051200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100012190","name":"Ministry of Science and Higher Education of the Russian Federation","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100012190","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Two novel cocrystals of zwitterionic trimethylglycine (TMG) with 2,6-dichlorophenol [TMG\u20222,6-dichlorophenol] (1:1) and 2,6-dibromophenol [TMG\u20222,6-dibromophenol] (1:2) are synthesized and structurally characterized using single crystal X-ray diffraction. To estimate the energy of various intermolecular interactions, periodic DFT calculations were performed followed by Bader analysis of the crystalline electron density. TMG molecules form dimers in [TMG\u20222,6-dichlorophenol] (1:1). Its supramolecular structure is governed by the primary charge-assisted H-bonds (~60 kJ\/mol) and supported by C\u2013H\u2219\u2219\u2219O contacts (~12 kJ\/mol). Cl\/Br substitution introduces a more potent halogen-bonding donor. The Br\u2219\u2219\u2219O\u2212 interaction (~10 kJ\/mol) is strong enough to reorganize the packing into a catemeric motif. As a result, TMG molecules form infinite chains in [TMG\u20222,6-dibromophenol] (1:2). This illustrates that \u201cfine tuning\u201d is not merely about changing distances, but about shifting the entire energy hierarchy of the crystal. Two-dimensional fingerprint diagrams (2D diagrams) obtained from the Hirshfeld surface and Bader\u2019s analysis of the crystalline electron density give significantly different values of the contributions of the H\u2219\u2219\u2219H contacts, 28% vs. 5% respectively. The main reason for this discrepancy is the large number of relatively short intermolecular H\u2219\u2219\u2219H contacts without a critical bond point in trimethylglycine cocrystals.<\/jats:p>","DOI":"10.3390\/molecules31061047","type":"journal-article","created":{"date-parts":[[2026,3,23]],"date-time":"2026-03-23T08:47:42Z","timestamp":1774255662000},"page":"1047","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Tuning Supramolecular Structure in Trimethylglycine Cocrystals: Competition Between Hydrogen and Halogen Bonding upon Cl\/Br Substitution"],"prefix":"10.3390","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3336-4022","authenticated-orcid":false,"given":"Andrei V.","family":"Churakov","sequence":"first","affiliation":[{"name":"N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii Prosp. 31, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6762-004X","authenticated-orcid":false,"given":"Alexander G.","family":"Medvedev","sequence":"additional","affiliation":[{"name":"N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii Prosp. 31, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7020-0134","authenticated-orcid":false,"given":"Anastasia V.","family":"Shishkina","sequence":"additional","affiliation":[{"name":"Scientific Department, Northern (Arctic) Federal University, Severnaya Dvina Emb. 17, 163001 Arkhangelsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0006-7374-626X","authenticated-orcid":false,"given":"Nikita E.","family":"Frolov","sequence":"additional","affiliation":[{"name":"V. M. Gorbatov Federal Research Center for Food Systems, Talalikhina St. 26, 109316 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0511-9903","authenticated-orcid":false,"given":"Mikhail V.","family":"Vener","sequence":"additional","affiliation":[{"name":"N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii Prosp. 31, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2026,3,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1007\/BF02942500","article-title":"Agro-Industrial Uses of Glycinebetaine","volume":"6","year":"2004","journal-title":"Sugar Tech"},{"key":"ref_2","first-page":"e05658","article-title":"Safety of Betaine as a Novel Food Pursuant to Regulation (EU) 2015\/2283","volume":"17","author":"Turck","year":"2019","journal-title":"EFSA J."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"50","DOI":"10.1034\/j.1600-0846.2003.00367.x","article-title":"The Ability of Betaine to Reduce the Irritating Effects of Detergents Assessed Visually, Histologically and by Bioengineering Methods","volume":"9","author":"Nicander","year":"2003","journal-title":"Ski. Res. 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