{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,27]],"date-time":"2026-10-27T15:53:16Z","timestamp":1793116396365,"version":"4.5.0"},"reference-count":64,"publisher":"American Chemical Society (ACS)","issue":"36","license":[{"start":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T00:00:00Z","timestamp":1788307200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100005285","name":"Funda??o de Amparo ? Pesquisa do Estado de Goi?s","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100005285","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient?fico e Tecnol?gico","doi-asserted-by":"publisher","award":["420767\/2023-1"],"award-info":[{"award-number":["420767\/2023-1"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004809","name":"Financiadora de Estudos e Projetos","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002322","name":"Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,15]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The increasing prevalence of polymorphism and multicomponent crystal forms in active pharmaceutical ingredients demands rigorous structural characterization tools for quality control. Here, lamivudine and three pharmaceutical salts, hydrochloride, salicylate monohydrate, and hydrogen phthalate, were investigated by combining powder X-ray diffraction, 13C solid-state NMR spectroscopy, and two DFT-based methods for theoretical chemical-shift prediction: gauge including projected augmented wave (GIPAW) and gauge including atomic orbital (GIAO). In statistical comparison of experimental and theoretical chemical shifts, the GIPAW method consistently outperformed GIAO for all four crystalline forms, as evidenced by lower median errors and higher Kendall\u2019s \u03c4 correlation coefficient values, a rank-order metric that proved more discriminating than Pearson\u2019s R alone. The superior performance of GIPAW is attributed to its explicit treatment of periodic boundary conditions, which faithfully reproduces the crystallographic environment of the solid state. In addition, QTAIM topological analysis and natural bond orbital (NBO) second-order perturbation theory were used to characterize all inter- and intramolecular hydrogen bonds in each form. Two strong, nearly symmetric O\u00b7\u00b7\u00b7H\u00b7\u00b7\u00b7O interactions in the hydrogen phthalate salt are reported here for the first time, consistent with the anomalously low pKa2 of ortho-phthalic acid. These results demonstrate that the combined use of periodic GIPAW NMR calculations with QTAIM\/NBO analysis constitutes a powerful, generally applicable strategy for the unequivocal structural characterization of pharmaceutical solid forms, with direct implications for the physicochemical quality control of drug substances.<\/jats:p>","DOI":"10.1021\/acsomega.6c03134","type":"journal-article","created":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T16:19:57Z","timestamp":1788452397000},"page":"53927-53937","source":"Crossref","is-referenced-by-count":1,"title":["Combining X-ray\nDiffraction, Solid-State NMR,\nand Computational Chemistry for Structural Insights and Performance\nEvaluation of GIPAW\/GIAO 13C Chemical-Shift Calculations\nfor Lamivudine and Three Pharmaceutical Salts"],"prefix":"10.1021","volume":"11","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1706-5751","authenticated-orcid":true,"given":"Jefferson R.","family":"Dias-Silva","sequence":"first","affiliation":[{"name":"Universidade Federal de Goia\u0301s , , CP 131 , ,","place":["Goia\u0302nia-GO, Brazil, 74001-970"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vini\u0301cius S.","family":"Ferreira","sequence":"additional","affiliation":[{"name":"Universidade Federal de Goia\u0301s , , CP 131 , ,","place":["Goia\u0302nia-GO, Brazil, 74001-970"]},{"name":"Instituto Federal de Goia\u0301s , R. 75 n. 46 , ,","place":["Goia\u0302nia-GO, Brazil, 74055-110"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9004-0927","authenticated-orcid":true,"given":"Felipe T.","family":"Martins","sequence":"additional","affiliation":[{"name":"Instituto de Qui\u0301mica, Universidade Federal de Alfenas , , ,","place":["Alfenas, MG, Brazil, 37130-001"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Valdemar","family":"Lacerda Ju\u0301nior","sequence":"additional","affiliation":[{"name":"Universidade Federal do Espi\u0301rito Santo , , ,","place":["Vito\u0301ria-ES, Brazil, 29075-910"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pedro L.","family":"de Souza","sequence":"additional","affiliation":[{"name":"Universidade Federal de Goia\u0301s , , CP 131 , ,","place":["Goia\u0302nia-GO, Brazil, 74001-970"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thiago M. F.","family":"Marinho","sequence":"additional","affiliation":[{"name":"Universidade Federal de Goia\u0301s , , CP 131 , ,","place":["Goia\u0302nia-GO, Brazil, 74001-970"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luiz H. K.","family":"Queiroz Ju\u0301nior","sequence":"additional","affiliation":[{"name":"Universidade Federal de Goia\u0301s , , CP 131 , ,","place":["Goia\u0302nia-GO, Brazil, 74001-970"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,2]]},"reference":[{"key":"2026091510090895200_cit1","doi-asserted-by":"publisher","first-page":"235","DOI":"10.1016\/j.addr.2003.10.004","article-title":"Pharmaceutical solid\npolymorphism in drug development and regulation","volume":"56","author":"Raw","year":"2004","journal-title":"Adv. Drug Delivery Rev."},{"key":"2026091510090895200_cit2","doi-asserted-by":"publisher","first-page":"351","DOI":"10.1039\/b516057j","article-title":"NMR studies\nof organic polymorphs & solvates","volume":"131","author":"Harris","year":"2006","journal-title":"Analyst"},{"key":"2026091510090895200_cit3","doi-asserted-by":"publisher","first-page":"608","DOI":"10.1134\/S1063774511030059","article-title":"Structural\npolymorphism and solubility of medicinal drugs (Using Perindopril\nas an Example)","volume":"56","author":"Bogdanov","year":"2011","journal-title":"Crystallogr. Rep."},{"key":"2026091510090895200_cit4","doi-asserted-by":"publisher","first-page":"2143","DOI":"10.1002\/jps.23117","article-title":"Lamivudine salts with\nimproved solubilities","volume":"101","author":"Martins","year":"2012","journal-title":"J. Pharm. Sci."},{"key":"2026091510090895200_cit5","doi-asserted-by":"publisher","first-page":"20486","DOI":"10.1039\/C5RA01398D","article-title":"The enantiopreference in the solid\nstate probed in lamivudine crystal forms with mandelic acid","volume":"5","author":"da Silva","year":"2015","journal-title":"RSC Adv."},{"key":"2026091510090895200_cit6","doi-asserted-by":"publisher","first-page":"4562","DOI":"10.1039\/c2ce25386k","article-title":"Salts of\nthe anti-HIV drug lamivudine with phthalic and salicylic acids","volume":"14","author":"Capeletti da Silva","year":"2012","journal-title":"CrystEngComm"},{"key":"2026091510090895200_cit7","doi-asserted-by":"publisher","first-page":"573","DOI":"10.5935\/0103-5053.20130071","article-title":"Chemical interactions\nstudy of antiretroviral drugs\nefavirenz and lamivudine concerning the development of stable fixed-dose\ncombination formulations for AIDS treatment","volume":"24","author":"Gomes","year":"2013","journal-title":"J. Braz. Chem. Soc."},{"key":"2026091510090895200_cit8","doi-asserted-by":"publisher","first-page":"2373","DOI":"10.1039\/c2ce06303d","article-title":"Toward supramolecular architectures\nof the anti-HIV drug lamivudine: understanding the effect of the inclusion\nof water in a hydrochloride form","volume":"14","author":"Ellena","year":"2012","journal-title":"CrystEngComm"},{"key":"2026091510090895200_cit9","doi-asserted-by":"publisher","first-page":"8069","DOI":"10.1039\/c3cp41095a","article-title":"Powder crystallography of pharmaceutical\nmaterials by combined crystal structure prediction and solid-state\n1H NMR spectroscopy","volume":"15","author":"Baias","year":"2013","journal-title":"Phys. Chem. Chem. Phys."},{"key":"2026091510090895200_cit10","doi-asserted-by":"publisher","first-page":"902","DOI":"10.1021\/jp810138y","article-title":"Characterizing\nslight structural disorder in solids by combined solid-state NMR and\nfirst principles calculations","volume":"113","author":"Cadars","year":"2009","journal-title":"J. Phys. Chem.\nA"},{"key":"2026091510090895200_cit11","volume-title":"NMR crystallography","author":"Harris","year":"2009"},{"key":"2026091510090895200_cit12","doi-asserted-by":"publisher","first-page":"3141","DOI":"10.1039\/C4CE00012A","article-title":"Structure determination of the theophylline-nicotinamide cocrystal:\na combined powder XRD, 1D solid-state NMR, and theoretical calculation\nstudy","volume":"16","author":"Li","year":"2014","journal-title":"CrystEngComm"},{"key":"2026091510090895200_cit13","doi-asserted-by":"publisher","first-page":"275","DOI":"10.1016\/j.addr.2003.10.020","article-title":"High-throughput\ncrystallization: polymorphs, salts, co-crystals and solvates of pharmaceutical\nsolids","volume":"56","author":"Morissette","year":"2004","journal-title":"Adv. Drug Delivery Rev."},{"key":"2026091510090895200_cit14","doi-asserted-by":"publisher","first-page":"551","DOI":"10.1016\/j.molstruc.2014.07.020","article-title":"The origin of the splitting of 13C\nand 15N NMR signals of 3(5)-phenyl-5(3)-methylpyrazolium chloride\nand bromide in the solid state: Quantum Espresso calculations","volume":"1075","author":"Alkorta","year":"2014","journal-title":"J. Mol. Struct."},{"key":"2026091510090895200_cit15","doi-asserted-by":"publisher","first-page":"6711","DOI":"10.1021\/jp302128r","article-title":"Combining multinuclear\nhigh-resolution solid-state MAS NMR and computational\nmethods for resonance assignment of glutathione tripeptide","volume":"116","author":"Sardo","year":"2012","journal-title":"J. Phys. Chem. A"},{"key":"2026091510090895200_cit16","doi-asserted-by":"publisher","first-page":"496","DOI":"10.1002\/mrc.3827","article-title":"Real-time mechanistic\nmonitoring of an acetal hydrolysis using ultrafast 2D NMR","volume":"50","author":"Queiroz","year":"2012","journal-title":"Magn. Reson. Chem."},{"key":"2026091510090895200_cit17","doi-asserted-by":"publisher","first-page":"2315","DOI":"10.1039\/b406861k","article-title":"Solid state NMR studies and density functional theory\n(DFT) calculations of conformers of quercetin","volume":"2","author":"Olejniczak","year":"2004","journal-title":"Org. Biomol. Chem."},{"key":"2026091510090895200_cit18","doi-asserted-by":"publisher","first-page":"140","DOI":"10.1002\/mrc.2722","article-title":"NMR property calculations and experimental study of\nthe 1,6-epoxycarvone and \u03b1-epoxypinene: a comparison\nof models","volume":"49","author":"Queiroz","year":"2011","journal-title":"Magn. Reson. Chem."},{"key":"2026091510090895200_cit19","doi-asserted-by":"publisher","first-page":"42","DOI":"10.1002\/cmr.a.10096","article-title":"Calculations\nof chemical shieldings: Theory and applications","volume":"20A","author":"Facelli","year":"2004","journal-title":"Concepts Magn. Reson., Part A"},{"key":"2026091510090895200_cit20","doi-asserted-by":"publisher","first-page":"357","DOI":"10.1016\/j.molstruc.2018.07.112","article-title":"Unequivocal structural assignments\nof three cardanol\nderivatives: An experimental and theoretical approach","volume":"1175","author":"Barbosa","year":"2019","journal-title":"J. Mol. Struct."},{"key":"2026091510090895200_cit21","doi-asserted-by":"publisher","first-page":"6194","DOI":"10.1021\/acs.jpca.9b03587","article-title":"Single-Crystal NMR Characterization\nof Halogen Bonds","volume":"123","author":"Xu","year":"2019","journal-title":"J. Phys. Chem. A"},{"key":"2026091510090895200_cit22","doi-asserted-by":"publisher","first-page":"789","DOI":"10.1080\/00268977400100711","article-title":"Self-consistent\nperturbation theory of diamagnetism","volume":"27","author":"Ditchfield","year":"1974","journal-title":"Mol. Phys."},{"key":"2026091510090895200_cit23","doi-asserted-by":"publisher","first-page":"8251","DOI":"10.1021\/ja00179a005","article-title":"Efficient\nimplementation of the gauge-independent\natomic orbital method for NMR chemical shift calculations","volume":"112","author":"Wolinski","year":"1990","journal-title":"J. Am. Chem. Soc."},{"key":"2026091510090895200_cit24","doi-asserted-by":"publisher","first-page":"202","DOI":"10.1016\/j.ssnmr.2008.10.002","article-title":"13C, 15N CPMAS NMR and GIAO DFT calculations\nof stereoisomeric oxindole alkaloids from Cat\u2019s Claw (Uncaria\ntomentosa)","volume":"34","author":"Paradowska","year":"2008","journal-title":"Solid State Nucl. Magn. Reson."},{"key":"2026091510090895200_cit25","doi-asserted-by":"publisher","DOI":"10.1007\/s00894-019-4025-4","article-title":"Solid state NMR and\ncomputational studies on cyclopentadienyl lithium","volume":"25","author":"Jiao","year":"2019","journal-title":"J. Mol. Model."},{"key":"2026091510090895200_cit26","doi-asserted-by":"publisher","first-page":"5","DOI":"10.1002\/mrc.1894","article-title":"Structural elucidation\nof nitro-substituted five-membered\naromatic heterocycles utilizing GIAO DFT calculations","volume":"45","author":"Katritzky","year":"2007","journal-title":"Magn. Reson. Chem."},{"key":"2026091510090895200_cit27","doi-asserted-by":"publisher","first-page":"7763","DOI":"10.1016\/j.tet.2005.05.101","article-title":"Calculated NMR as a tool for structural\nelucidation of jungianol and mutisianthol","volume":"61","author":"da Silva","year":"2005","journal-title":"Tetrahedron"},{"key":"2026091510090895200_cit28","doi-asserted-by":"publisher","first-page":"9","DOI":"10.1016\/j.molstruc.2019.07.034","article-title":"Structural,\nspectroscopic and electronic properties of 4-bromo-5-fluoro-2-((3-nitrophenylimino)\nmethyl) phenol Schiff-base molecule: Experimental and theoretical\ninvestigations","volume":"1197","author":"Bozkurt","year":"2019","journal-title":"J. Mol. Struct."},{"key":"2026091510090895200_cit29","doi-asserted-by":"publisher","first-page":"465","DOI":"10.1088\/1361-648X\/aa8f79","article-title":"Advanced capabilities\nfor materials modelling with QUANTUM ESPRESSO","volume":"29","author":"Giannozzi","year":"2017","journal-title":"J. Phys.: Condens. Matter"},{"key":"2026091510090895200_cit30","doi-asserted-by":"publisher","first-page":"1080","DOI":"10.1002\/jcc.22940","article-title":"Vibrational averaging of the chemical shift in crystalline \u03b1-glycine","volume":"33","author":"Drac\u030ci\u0301nsky\u0301","year":"2012","journal-title":"J. Comput. Chem."},{"key":"2026091510090895200_cit31","doi-asserted-by":"publisher","first-page":"285","DOI":"10.1127\/0935-1221\/2011\/0023-2090","article-title":"Theoretical infrared spectrum of\nOH-defects in forsterite","volume":"23","author":"Balan","year":"2011","journal-title":"Eur. J. Mineral."},{"key":"2026091510090895200_cit32","doi-asserted-by":"publisher","first-page":"210","DOI":"10.1038\/nnano.2008.67","article-title":"Monitoring\ndopants\nby Raman scattering in an electrochemically top-gated graphene transistor","volume":"3","author":"Das","year":"2008","journal-title":"Nat. Nanotechnol."},{"key":"2026091510090895200_cit33","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevB.63.245101","article-title":"All-electron magnetic response with pseudopotentials: NMR chemical\nshifts","volume":"63","author":"Pickard","year":"2001","journal-title":"Phys. Rev. B"},{"key":"2026091510090895200_cit34","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/j.ssnmr.2011.04.006","article-title":"The PAW\/GIPAW\napproach for computing NMR parameters: A new dimension added to NMR\nstudy of solids","volume":"40","author":"Charpentier","year":"2011","journal-title":"Solid State Nucl. Magn. Reson."},{"key":"2026091510090895200_cit35","doi-asserted-by":"publisher","first-page":"29952","DOI":"10.1021\/jp510021z","article-title":"First-Principles Calculations\nand Analysis of 29Si Nuclear Magnetic\nResonance Chemical Shifts in Silicon Oxycarbide Ceramics","volume":"118","author":"Nimmo","year":"2014","journal-title":"J. Phys. Chem. C"},{"key":"2026091510090895200_cit36","doi-asserted-by":"publisher","first-page":"23625","DOI":"10.1021\/acs.jpcc.6b08041","article-title":"Direct Evidence\nof Chelated Geometry of Catechol on TiO2 by a Combined Solid-State\nNMR and DFT Study","volume":"120","author":"Finkelstein-Shapiro","year":"2016","journal-title":"J. Phys. Chem. C"},{"key":"2026091510090895200_cit37","doi-asserted-by":"publisher","first-page":"11514","DOI":"10.1021\/acs.chemrev.1c00987","article-title":"Crystal\nEngineering of Pharmaceutical\nCo-crystals in the Discovery and Development of Improved Drugs","volume":"122","author":"Bolla","year":"2022","journal-title":"Chem. Rev."},{"key":"2026091510090895200_cit38","doi-asserted-by":"publisher","first-page":"171","DOI":"10.1107\/S2052520616003954","article-title":"The Cambridge Structural\nDatabase","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Crystallogr., Sect. B: Struct.\nSci."},{"key":"2026091510090895200_cit39","doi-asserted-by":"publisher","first-page":"466","DOI":"10.1107\/S0021889807067908","article-title":"Mercury CSD 2.0\n- new features for the visualization and investigation of crystal\nstructures","volume":"41","author":"Macrae","year":"2008","journal-title":"J. Appl. Crystallogr."},{"key":"2026091510090895200_cit40","doi-asserted-by":"publisher","first-page":"1800","DOI":"10.1063\/1.444076","article-title":"Spinning-sideband-free\nand spinning-sideband-only NMR spectra in spinning samples","volume":"77","author":"Dixon","year":"1982","journal-title":"J. Chem. Phys."},{"key":"2026091510090895200_cit41","doi-asserted-by":"publisher","first-page":"323","DOI":"10.1021\/mp0601345","article-title":"The salt-cocrystal continuum: the\ninfluence of crystal structure on ionization state","volume":"4","author":"Childs","year":"2007","journal-title":"Mol. Pharmaceutics"},{"key":"2026091510090895200_cit42","doi-asserted-by":"publisher","first-page":"2653","DOI":"10.1039\/a704709f","article-title":"\u2018Polymorphism\u2019in a\nnovel anti-viral agent: Lamivudine","volume":"2","author":"Harris","year":"1997","journal-title":"J. Chem.\nSoc., Perkin Trans. 2"},{"key":"2026091510090895200_cit43","doi-asserted-by":"publisher","first-page":"695","DOI":"10.1080\/00268978800101351","article-title":"An analysis of the\nhydrogen bond in BASE-HF complexes\nusing the theory of atoms in molecules","volume":"65","author":"Carroll","year":"1988","journal-title":"Mol.\nPhys."},{"key":"2026091510090895200_cit44","doi-asserted-by":"publisher","first-page":"387","DOI":"10.1080\/00268978800100281","article-title":"Prediction of the structures of hydrogen-bonded\ncomplexes using the Laplacian of the charge density","volume":"63","author":"Carroll","year":"1988","journal-title":"Mol. Phys."},{"key":"2026091510090895200_cit45","doi-asserted-by":"publisher","first-page":"9747","DOI":"10.1021\/j100024a016","article-title":"Characterization of CHO hydrogen\nbonds on the basis\nof the charge density","volume":"99","author":"Koch","year":"1995","journal-title":"J. Phys. Chem. A"},{"key":"2026091510090895200_cit46","doi-asserted-by":"publisher","first-page":"1943","DOI":"10.1063\/1.446956","article-title":"The characterization\nof atomic interactions","volume":"80","author":"Bader","year":"1984","journal-title":"J. Chem. Phys."},{"key":"2026091510090895200_cit47","doi-asserted-by":"crossref","DOI":"10.1093\/oso\/9780198551683.001.0001","volume-title":"Atoms in Molecules:\nA Quantum Theory; International Series of Monographs on Chemistry","author":"Bader","year":"1990"},{"key":"2026091510090895200_cit48","doi-asserted-by":"publisher","first-page":"893","DOI":"10.1021\/cr00005a013","article-title":"A quantum\ntheory of molecular structure and its applications","volume":"91","author":"Bader","year":"1991","journal-title":"Chem. Rev."},{"key":"2026091510090895200_cit49","doi-asserted-by":"publisher","first-page":"11154","DOI":"10.1021\/ja0017864","article-title":"Behavior of ylides containing N,\nO, and C atoms as hydrogen bond acceptors","volume":"122","author":"Rozas","year":"2000","journal-title":"J.\nAm. Chem. Soc."},{"key":"2026091510090895200_cit50","doi-asserted-by":"publisher","first-page":"899","DOI":"10.1021\/cr00088a005","article-title":"Intermolecular interactions from\na natural bond orbital, donor-acceptor viewpoint","volume":"88","author":"Reed","year":"1988","journal-title":"Chem. Rev."},{"key":"2026091510090895200_cit51","doi-asserted-by":"publisher","first-page":"99","DOI":"10.1002\/prot.340090204","article-title":"Hydrogen bonds involving\nsulfur atoms in proteins","volume":"9","author":"Gregoret","year":"1991","journal-title":"Proteins"},{"key":"2026091510090895200_cit52","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2020.128651","article-title":"Novel fused\npyridine derivatives\ncontaining pyrimidine moiety as prospective tyrosyl-tRNA synthetase\ninhibitors: Design, synthesis, pharmacokinetics and molecular docking\nstudies","volume":"1219","author":"Othman","year":"2020","journal-title":"J. Mol. Struct."},{"key":"2026091510090895200_cit53","doi-asserted-by":"publisher","first-page":"2022","DOI":"10.1107\/S0567740875006772","article-title":"A neutron\ndiffraction study of L-cysteine","volume":"31","author":"Kerr","year":"1975","journal-title":"Acta Crystallogr.,\nSect. B"},{"key":"2026091510090895200_cit54","doi-asserted-by":"publisher","first-page":"3613","DOI":"10.1021\/ja00744a012","article-title":"Hydrogen\nbonds involving sulfur. I. Hydrogen sulfide dimer","volume":"93","author":"Sabin","year":"1971","journal-title":"J. Am. Chem. Soc."},{"key":"2026091510090895200_cit55","doi-asserted-by":"publisher","first-page":"151","DOI":"10.1002\/prot.22327","article-title":"Geometric characteristics\nof hydrogen bonds involving sulfur atoms in proteins","volume":"76","author":"Zhou","year":"2009","journal-title":"Proteins"},{"key":"2026091510090895200_cit56","doi-asserted-by":"publisher","first-page":"191","DOI":"10.5487\/TR.2011.27.4.191","article-title":"Toxicological characterization of\nphthalic acid","volume":"27","author":"Bang","year":"2011","journal-title":"Toxicol. Res."},{"key":"2026091510090895200_cit57","doi-asserted-by":"publisher","first-page":"85","DOI":"10.1021\/je900273d","article-title":"Acid- Base\nDissociation Constants of o-Phthalic Acid in Acetonitrile\/Water Mixtures\nover the (15 to 50)\u00b0 C Temperature Range and Related Thermodynamic\nQuantities","volume":"55","author":"Gagliardi","year":"2010","journal-title":"J. Chem. Eng. Data"},{"key":"2026091510090895200_cit58","doi-asserted-by":"publisher","first-page":"35","DOI":"10.1016\/j.cplett.2016.04.075","article-title":"Effects of\nstructural differences on the NMR chemical shifts in cinnamic acid\nderivatives: Comparison of GIAO and GIPAW calculations","volume":"653","author":"Szeleszczuk","year":"2016","journal-title":"Chem. Phys. Lett."},{"key":"2026091510090895200_cit59","doi-asserted-by":"publisher","first-page":"101662","DOI":"10.1016\/j.ssnmr.2020.101662","article-title":"Investigating discrepancies\nbetween experimental solid-state NMR and GIPAW calculation: N = C-N 13C and OH\u00b7\u00b7\u00b7O 1H chemical shifts\nin pyridinium fumarates and their cocrystals","volume":"108","author":"Corlett","year":"2020","journal-title":"Solid State Nucl. Magn. Reson."},{"key":"2026091510090895200_cit60","doi-asserted-by":"publisher","first-page":"176","DOI":"10.2307\/2347986","article-title":"Algorithm\nAS 181: the W test for normality","volume":"31","author":"Royston","year":"1982","journal-title":"Appl. Stat."},{"key":"2026091510090895200_cit61","doi-asserted-by":"publisher","first-page":"547","DOI":"10.2307\/2986146","article-title":"Remark AS\nR94: A remark on algorithm AS 181: The W-test for normality","volume":"44","author":"Royston","year":"1995","journal-title":"Appl. Stat."},{"key":"2026091510090895200_cit62","doi-asserted-by":"publisher","first-page":"23","DOI":"10.1007\/BF02294183","article-title":"Sample size requirements for estimating pearson, kendall\nand spearman correlations","volume":"65","author":"Bonett","year":"2000","journal-title":"Psychometrika"},{"key":"2026091510090895200_cit63","doi-asserted-by":"publisher","first-page":"81","DOI":"10.1093\/biomet\/30.1-2.81","article-title":"A New Measure\nof Rank Correlation","volume":"30","author":"Kendall","year":"1938","journal-title":"Biometrika"},{"key":"2026091510090895200_cit64","doi-asserted-by":"publisher","first-page":"164","DOI":"10.1002\/mrc.4674","article-title":"A theoretical NMR study\nof selected\nbenzazoles: Comparison of GIPAW and GIAO-PCM (DMSO) calculations","volume":"56","author":"Mari\u0301n-Luna","year":"2018","journal-title":"Magn. Reson. Chem."}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.6c03134","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/11\/36\/53927\/68204760\/acsomega.6c03134.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/11\/36\/53927\/68204760\/acsomega.6c03134.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,15]],"date-time":"2026-09-15T14:51:03Z","timestamp":1789483863000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/11\/36\/53927\/5405592\/Combining-X-ray-Diffraction-Solid-State-NMR-and"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,2]]},"references-count":64,"journal-issue":{"issue":"36","published-online":{"date-parts":[[2026,9,2]]},"published-print":{"date-parts":[[2026,9,15]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.6c03134","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,2]]}}}