{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T02:51:50Z","timestamp":1760151110796,"version":"build-2065373602"},"reference-count":32,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2022,2,22]],"date-time":"2022-02-22T00:00:00Z","timestamp":1645488000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Symmetry"],"abstract":"<jats:p>Herein we present two new organic co-crystals obtained through a simple solution growth process based on an acetamidophenol molecule, either paracetamol or metacetamol, and on 7,7,8,8-tetracyanoquinodimethane (TCNQ). These co-crystals are part of a family of potential organic charge transfer complexes, where the acetamidophenol molecule behaves as an electron donor and TCNQ behaves as an electron acceptor. Due to the sub-micron size of the crystalline domains, 3D electron diffraction was employed for the structure characterization of both systems. Paracetamol-TCNQ structure was solved by standard direct methods, while the analysis of metacetamol-TCNQ was complicated by the low resolution of the available diffraction data and by the low symmetry of the system. The structure determination of metacetamol-TCNQ was eventually achieved after merging two data sets and combining direct methods with simulated annealing. Our study reveals that both paracetamol-TCNQ and metacetamol-TCNQ systems crystallize in a 1:1 stoichiometry, assembling in a mixed-stack configuration and adopting a non-centrosymmetric P1 symmetry. It appears that paracetamol and metacetamol do not form a strong structural scaffold based on hydrogen bonding, as previously observed for orthocetamol-TCNQ and orthocetamol-TCNB (1,2,4,5-tetracyanobenzene) co-crystals.<\/jats:p>","DOI":"10.3390\/sym14030431","type":"journal-article","created":{"date-parts":[[2022,2,22]],"date-time":"2022-02-22T22:35:00Z","timestamp":1645569300000},"page":"431","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Two New Organic Co-Crystals Based on Acetamidophenol Molecules"],"prefix":"10.3390","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9554-2969","authenticated-orcid":false,"given":"Iryna","family":"Andrusenko","sequence":"first","affiliation":[{"name":"Center for Materials Interfaces, Electron Crystallography, Istituto Italiano di Tecnologia, Viale Rinaldo Piaggio 34, 56025 Pontedera, Italy"}]},{"given":"Joseph","family":"Hitchen","sequence":"additional","affiliation":[{"name":"Complex Functional Materials Group, School of Chemistry, University of Bristol, Cantock\u2019s Close, Bristol BS8 1TS, UK"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9543-9064","authenticated-orcid":false,"given":"Enrico","family":"Mugnaioli","sequence":"additional","affiliation":[{"name":"Center for Materials Interfaces, Electron Crystallography, Istituto Italiano di Tecnologia, Viale Rinaldo Piaggio 34, 56025 Pontedera, Italy"}]},{"given":"Jason","family":"Potticary","sequence":"additional","affiliation":[{"name":"Complex Functional Materials Group, School of Chemistry, University of Bristol, Cantock\u2019s Close, Bristol BS8 1TS, UK"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2816-0191","authenticated-orcid":false,"given":"Simon R.","family":"Hall","sequence":"additional","affiliation":[{"name":"Complex Functional Materials Group, School of Chemistry, University of Bristol, Cantock\u2019s Close, Bristol BS8 1TS, UK"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9542-3783","authenticated-orcid":false,"given":"Mauro","family":"Gemmi","sequence":"additional","affiliation":[{"name":"Center for Materials Interfaces, Electron Crystallography, Istituto Italiano di Tecnologia, Viale Rinaldo Piaggio 34, 56025 Pontedera, Italy"}]}],"member":"1968","published-online":{"date-parts":[[2022,2,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"507","DOI":"10.1016\/j.ultramic.2006.10.007","article-title":"Towards automated diffraction tomography: Part I\u2014Data acquisition","volume":"107","author":"Kolb","year":"2007","journal-title":"Ultramicroscopy"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"e01345","DOI":"10.7554\/eLife.01345","article-title":"Threedimensional electron crystallography of protein microcrystals","volume":"2","author":"Shi","year":"2013","journal-title":"eLife"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1315","DOI":"10.1021\/acscentsci.9b00394","article-title":"3D electron diffraction: The nanocrystallography revolution","volume":"5","author":"Gemmi","year":"2019","journal-title":"ACS Cent. 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