{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,26]],"date-time":"2026-03-26T18:34:25Z","timestamp":1774550065662,"version":"3.50.1"},"reference-count":63,"publisher":"Walter de Gruyter GmbH","issue":"2","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2019,2,25]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:p>Crystal structures, Hirshfeld surface analysis and a computational study have been carried out on 2-oxo-2<jats:italic>H<\/jats:italic>-chromene-3-carboxylates. Crystal structures are reported for ethyl R-2-oxo-2<jats:italic>H<\/jats:italic>-chromene-3-carboxylate derivatives, <jats:bold>2a<\/jats:bold>: R=6-Me, <jats:bold>2b<\/jats:bold>: 7-Me, <jats:bold>2c<\/jats:bold>: 7-Me, <jats:bold>2d<\/jats:bold>: R=7-MeO. In contrast to 2-oxo-2H-chromene-3-carboxamides, <jats:bold>1<\/jats:bold>, in which classical intramolecular N\u2013H\u00b7\u00b7\u00b7O hydrogen bonds stabilize planar structures and hinder rotation of the amido group out of the coumarin plane in <jats:bold>2<\/jats:bold>, without an equivalent hydrogen bond, there is a greater rotational freedom of the carboxylate group. The interplanar angles between the coumarin core and its attached \u2013C(O)\u2013R substituent in crystalline <jats:bold>2a<\/jats:bold>, <jats:bold>2b<\/jats:bold>, <jats:bold>2c<\/jats:bold> and <jats:bold>2d<\/jats:bold> are 10.41(6), 36.65(6), 10.4(2) and 5.64(6)\u00b0, respectively, with distances between the carbonyl oxygen atoms of 2.8255(16), 2.9278(16), 4.226(2) and 2.8328(14) \u00c5, respectively. A theoretical study of molecular conformations was carried out at the M06-2X density level with the 6-31+G(d) and aug-cc-pVTZ basis sets, in methanol solution modeled by PCM, indicated that the most stable conformations had the carbonyl group of the ester in the plane of the coumarin core: the <jats:italic>s-cis<\/jats:italic> arrangement of the ester carbonyl and the 2-oxo moieties being the slightly more stable than the <jats:italic>s-trans<\/jats:italic> form by less than 0.5 kcal\/mol. The experimental conformations of <jats:bold>2a<\/jats:bold> and <jats:bold>2d<\/jats:bold> match well the low energy <jats:italic>s-cis<\/jats:italic> arrangement, and <jats:bold>2c<\/jats:bold> matches the slightly lesser stable <jats:italic>s-trans<\/jats:italic> arrangement found in the theoretical study. A survey of the molecular conformations of more than 50 2<jats:italic>H<\/jats:italic>-chromene-3-carboxylates derivatives in the CCDC data base indicated two distinct groupings of conformations, <jats:italic>s-cis<\/jats:italic> and <jats:italic>s-trans<\/jats:italic>, each with interplanar angles &lt;30\u00b0.<\/jats:p>","DOI":"10.1515\/zkri-2018-2117","type":"journal-article","created":{"date-parts":[[2019,1,24]],"date-time":"2019-01-24T09:56:01Z","timestamp":1548323761000},"page":"85-99","source":"Crossref","is-referenced-by-count":1,"title":["Crystal structures, Hirsfeld surface analysis and a computational study of four ethyl 2-oxo-2<i>H<\/i>-chromene-3-carboxylate derivatives: a survey of organyl 2-oxo-2<i>H<\/i>-chromene-3-carboxylate structures"],"prefix":"10.1515","volume":"234","author":[{"given":"Ligia R.","family":"Gomes","sequence":"first","affiliation":[{"name":"FP-ENAS-Faculdade de Ci\u00eancias de Sa\u00fade, Escola Superior de Sa\u00fade da UFP, Universidade Fernando Pessoa , Rua Carlos da Maia, 296 , P-4200-150 Porto , Portugal"},{"name":"REQUIMTE, Departamento de Qu\u00edmica e Bioqu\u00edmica , Faculdade de Ci\u00eancias da Universidade do Porto , Rua do Campo Alegre, 687 , P-4169-007, Porto , Portugal"}]},{"given":"John N.","family":"Low","sequence":"additional","affiliation":[{"name":"Department of Chemistry , University of Aberdeen , Meston Walk, Old Aberdeen, AB24 3UE , Scotland , UK"}]},{"given":"Tanja","family":"van Mourik","sequence":"additional","affiliation":[{"name":"School of Chemistry, University of St. Andrews , North Haugh, St. Andrews, Fife KY16 9ST , Scotland , UK"}]},{"given":"Ligia S.","family":"da Silveira Pinto","sequence":"additional","affiliation":[{"name":"Universidade Federal do Rio de Janeiro, Instituto de Qu\u00edmica , Departamento de Qu\u00edmica Org\u00e2nica , CP 68563, 21945-970 , Rio de Janeiro , Brazil"},{"name":"Instituto de Tecnologia em F\u00e1rmacos e Farmanguinhos, Funda\u00e7\u00e3o Oswaldo Cruz , 21041-250 Rio de Janeiro, RJ , Brazil"}]},{"given":"Marcus V.N.","family":"de Souza","sequence":"additional","affiliation":[{"name":"Instituto de Tecnologia em F\u00e1rmacos e Farmanguinhos, Funda\u00e7\u00e3o Oswaldo Cruz , 21041-250 Rio de Janeiro, RJ , Brazil"}]},{"given":"J\u00e1mes L.","family":"Wardell","sequence":"additional","affiliation":[{"name":"Department of Chemistry , University of Aberdeen , Meston Walk, Old Aberdeen, AB24 3UE , Scotland , UK"},{"name":"Instituto de Tecnologia em F\u00e1rmacos e Farmanguinhos, Funda\u00e7\u00e3o Oswaldo Cruz , 21041-250 Rio de Janeiro, RJ , Brazil"}]}],"member":"374","published-online":{"date-parts":[[2019,1,24]]},"reference":[{"key":"2025051309551209052_j_zkri-2018-2117_ref_001_w2aab3b7d169b1b6b1ab2b1b1Aa","doi-asserted-by":"crossref","unstructured":"M. Costa, T. A. Dias, A. Brito, F. Proenca, Eur. J. Med. Chem. 2016, 123, 487.","DOI":"10.1016\/j.ejmech.2016.07.057"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_002_w2aab3b7d169b1b6b1ab2b1b2Aa","doi-asserted-by":"crossref","unstructured":"E. C. Gaudino, S. Tagliapietra, K. Martina, G. Palmisano, G. Cravotto, RSC Adv. 2016, 6, 46394.","DOI":"10.1039\/C6RA07071J"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_003_w2aab3b7d169b1b6b1ab2b1b3Aa","doi-asserted-by":"crossref","unstructured":"H. Wei, J. Ruan, X. Zhanga, RSC Adv.2016, 6, 846.","DOI":"10.1039\/C5RA26294A"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_004_w2aab3b7d169b1b6b1ab2b1b4Aa","doi-asserted-by":"crossref","unstructured":"B. J. Connell, S.-Y. Chang, E. Prakash, R. Yousfi, V. Mohan, W. Posch, D. Wilflingseder, C. Moog, E. N. Kodama, P. Clayette, PLoS One2016, 11, e0165386.","DOI":"10.1371\/journal.pone.0165386"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_005_w2aab3b7d169b1b6b1ab2b1b5Aa","doi-asserted-by":"crossref","unstructured":"D. Yu, M. Suzuki, L. Xie, S. L. Morris-Natschke, K.-H. Lee, Med. Res. Rev. 2003, 23, 322.","DOI":"10.1002\/med.10034"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_006_w2aab3b7d169b1b6b1ab2b1b6Aa","doi-asserted-by":"crossref","unstructured":"S. K. Yusufzai, H. H. Osman, M. S. Khan, S. Mohamad, O. Sulaiman, T. Parumasivam, J. A. Gansau, N. Johansah, Noviany, Med. Chem. Res. 2017, 26, 1139.","DOI":"10.1007\/s00044-017-1820-2"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_007_w2aab3b7d169b1b6b1ab2b1b7Aa","doi-asserted-by":"crossref","unstructured":"G. X. Pang, C. Niu, N. Mamat, H. A. Aisa, Bioorg. Med. Chem. Lett.2017, 27, 2674.","DOI":"10.1016\/j.bmcl.2017.04.039"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_008_w2aab3b7d169b1b6b1ab2b1b8Aa","doi-asserted-by":"crossref","unstructured":"J. Suthiwong, Y. Thongsri, C. Yenjai, Nat. Prod. Res.2017, 31, 453.","DOI":"10.1080\/14786419.2016.1188100"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_009_w2aab3b7d169b1b6b1ab2b1b9Aa","doi-asserted-by":"crossref","unstructured":"G. Kirsch, A. B. Abdelwahab, P. Chaimbault, Molecules2016, 21, 322.","DOI":"10.3390\/molecules21101322"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_010_w2aab3b7d169b1b6b1ab2b1c10Aa","doi-asserted-by":"crossref","unstructured":"V. T. Angelova, V. Valcheva, N. G. Vassilev, R. Buyukliev, G. Momekov, I. Dimitrov, L. Saso, M. Djukic, B. Shivachev, Bioorg. Med. Chem. Lett.2017, 27, 223.","DOI":"10.1016\/j.bmcl.2016.11.071"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_011_w2aab3b7d169b1b6b1ab2b1c11Aa","unstructured":"R. S. Keni, B. S. Sasidhar, B. M. Nagaraja, M. A. Santos, Eur. J. Med. Chem. 2015, 100, 257."},{"key":"2025051309551209052_j_zkri-2018-2117_ref_012_w2aab3b7d169b1b6b1ab2b1c12Aa","doi-asserted-by":"crossref","unstructured":"S. Vazquez-Rodriguez, R. F. Gu\u00ed\u00f1ez, M. J. Matos, C. Olea-Azar, J. D. Maya, E. Uriarte, L. Santana, Med. Chem. 2016, 12, 537.","DOI":"10.2174\/1573406412666160107111809"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_013_w2aab3b7d169b1b6b1ab2b1c13Aa","doi-asserted-by":"crossref","unstructured":"R. Pingaew, A. Saekee, P. Mandi, C. Nantasenamat, S. Prachayasittikul, S. Ruchirawa, V. Prachayasittikul, Eur. J. Med. Chem. 2014, 85, 65.","DOI":"10.1016\/j.ejmech.2014.07.087"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_014_w2aab3b7d169b1b6b1ab2b1c14Aa","doi-asserted-by":"crossref","unstructured":"P. Jithin Raj, D. Bahulayan, Tetrahedron Lett. 2017, 58, 2122.","DOI":"10.1016\/j.tetlet.2017.04.052"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_015_w2aab3b7d169b1b6b1ab2b1c15Aa","doi-asserted-by":"crossref","unstructured":"A. Skoczynska, M. Ma\u0142ecka, M. Cieslak, J. Kazmierczak-Baranska, K. Krolewska-Golinska, A. Leniart, E. Budzisz, Polyhedron2017, 127, 307.","DOI":"10.1016\/j.poly.2017.02.011"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_016_w2aab3b7d169b1b6b1ab2b1c16Aa","doi-asserted-by":"crossref","unstructured":"J. Dandriyal, R. Singla, M. Kumar, V. Jaitak, Eur. J. Med. Chem. 2016, 119, 141.","DOI":"10.1016\/j.ejmech.2016.03.087"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_017_w2aab3b7d169b1b6b1ab2b1c17Aa","doi-asserted-by":"crossref","unstructured":"G. E. Escudero, C. H. Laino, G. A. Echeverr\u00eda, O. E. Piro, N. Martini, A. N. Rodr\u00edguez, J. J. M. Medina, L. L. T\u00e9vez, E. G. Ferrer, P. A. M. Williams, Chem. Bio. Interactions2016, 249, 46.","DOI":"10.1016\/j.cbi.2016.03.010"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_018_w2aab3b7d169b1b6b1ab2b1c18Aa","doi-asserted-by":"crossref","unstructured":"A. Montagut-Romans, M. Boulven, M. Jacolot, S. MoebsSanchez, C. Hasco\u00ebt, A. Hammed, S. Besse, M. Lemaire, E. Benoit, V. Lattard, F. Popowycz, Bioorg. Med. Chem. Lett. 2017, 27, 1598.","DOI":"10.1016\/j.bmcl.2017.02.017"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_019_w2aab3b7d169b1b6b1ab2b1c19Aa","doi-asserted-by":"crossref","unstructured":"G. Wang, J. Wang, D. He, X. Li, J. Li, Z. Peng, Chem. Bio. Drug. Des. 2017, 89, 456.","DOI":"10.1111\/cbdd.12867"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_020_w2aab3b7d169b1b6b1ab2b1c20Aa","doi-asserted-by":"crossref","unstructured":"I. Hueso-Falc\u00f3n, \u00c1. Amesty, L. Anaissi-Afonso, I. Lorenzo Castrillejo, F. Mach\u00edn, A. Est\u00e9vez, Bioorg. Med. Chem. Letts. 2017, 27, 484.","DOI":"10.1016\/j.bmcl.2016.12.040"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_021_w2aab3b7d169b1b6b1ab2b1c21Aa","doi-asserted-by":"crossref","unstructured":"J. Joubert, G. B. Foka, B. P. Repsold, D. W. Oliver, E. Kapp, S. F. Malan, Eur. J. Med. Chem. 2017, 125, 853.","DOI":"10.1016\/j.ejmech.2016.09.041"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_022_w2aab3b7d169b1b6b1ab2b1c22Aa","doi-asserted-by":"crossref","unstructured":"S. Hamulakova, M. Kozurkova, K. Kuca, Curr. Org. Chem. 2017, 21, 502.","DOI":"10.2174\/1385272820666160601155411"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_023_w2aab3b7d169b1b6b1ab2b1c23Aa","doi-asserted-by":"crossref","unstructured":"M. J. Matos, S. Vazquez-Rodriguez, A. Fonseca, E. Uriarte, L. Santana, F. Borges, Curr. Org. Chem. 2017, 21, 311.","DOI":"10.2174\/1385272820666161017170652"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_024_w2aab3b7d169b1b6b1ab2b1c24Aa","doi-asserted-by":"crossref","unstructured":"M. J. Matos, P. Janeiro, R. M. F. Gonzalez, S. Vilar, N. P. Tatonetti, L. Santana, E. Uriarte, F. Borges, J. A. Fontenla, D. Vina, Future Med. Chem. 2014, 6, 371.","DOI":"10.4155\/fmc.14.9"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_025_w2aab3b7d169b1b6b1ab2b1c25Aa","doi-asserted-by":"crossref","unstructured":"S. R. Trenor, A. R. Shultz, B. J. Love, T. E. Long, Chem. Rev. 2004, 104, 3059.","DOI":"10.1021\/cr030037c"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_026_w2aab3b7d169b1b6b1ab2b1c26Aa","doi-asserted-by":"crossref","unstructured":"\u015e. N. K. Elmas, F. Ozen, K. Koran, I. Yilmaz, A. O. Gorgulu, S. Erdemir, J. Fluorescence2017, 27, 463.","DOI":"10.1007\/s10895-016-1972-3"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_027_w2aab3b7d169b1b6b1ab2b1c27Aa","doi-asserted-by":"crossref","unstructured":"H. T. Srinivasa, H. N. Harishkumar, B. S. Palakshamurthy, J. Mol. Struct. 2017, 1131, 97.","DOI":"10.1016\/j.molstruc.2016.11.047"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_028_w2aab3b7d169b1b6b1ab2b1c28Aa","doi-asserted-by":"crossref","unstructured":"W. H. Perkin, J. Chem. Soc. 1868, 21, 181.","DOI":"10.1039\/JS8682100181"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_029_w2aab3b7d169b1b6b1ab2b1c29Aa","doi-asserted-by":"crossref","unstructured":"H. Pechmann, C. Duisberg, Ber. Dtsch. Chem. Ges. 1884, 17, 929.","DOI":"10.1002\/cber.188401701248"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_030_w2aab3b7d169b1b6b1ab2b1c30Aa","doi-asserted-by":"crossref","unstructured":"E. Knoevenagel, Ber. Dtsch. Chem. Ges.1904, 37, 4461.","DOI":"10.1002\/cber.19040370436"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_031_w2aab3b7d169b1b6b1ab2b1c31Aa","doi-asserted-by":"crossref","unstructured":"P.-H. E. Yao, S. Kumar, Y.-L. Liu, C.-P. E. Fang, C.-C. Liu, C.-M. Sun, Comb. Sci.2017, 19, 271.","DOI":"10.1021\/acscombsci.7b00004"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_032_w2aab3b7d169b1b6b1ab2b1c32Aa","doi-asserted-by":"crossref","unstructured":"P. Priyanka, R. K. Sharma, D. Katiyar, Synthesis2016, 48, 2303.","DOI":"10.1055\/s-0035-1560450"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_033_w2aab3b7d169b1b6b1ab2b1c33Aa","doi-asserted-by":"crossref","unstructured":"R. Pratap, V. J. Ram, Tetrahedron2017, 73, 2529.","DOI":"10.1016\/j.tet.2017.02.028"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_034_w2aab3b7d169b1b6b1ab2b1c34Aa","doi-asserted-by":"crossref","unstructured":"L. S. da S. Pinto, M. V. N. de Souza, Synthesis2017, 49, 2677.","DOI":"10.1055\/s-0036-1590201"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_035_w2aab3b7d169b1b6b1ab2b1c35Aa","doi-asserted-by":"crossref","unstructured":"L. R. Gomes, J. N. Low, F. Cagide, A. Gaspar, J Reis, F. Borges, Acta Crystallogr. 2013, B69, 294.","DOI":"10.1107\/S2052519213009676"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_036_w2aab3b7d169b1b6b1ab2b1c36Aa","doi-asserted-by":"crossref","unstructured":"T. C. Baddeley, L. R. Gomes, J. N. Low, J. M. S. Skakle, A. B. Turner, J. L. Wardell, G. J. R. Watson, Z. Kristallogr. 2017, 232, 317.","DOI":"10.1515\/zkri-2016-2020"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_037_w2aab3b7d169b1b6b1ab2b1c37Aa","doi-asserted-by":"crossref","unstructured":"W. T. Vellasco Junior, C. R. B. Gomes, T. R. A. Vasconcelos, J. L. Wardell, A. Otero-de-la-Roza, M. M. Jotani, E. R. T. Tiekink, Z. Kristallogr. 2016, 231, 663.","DOI":"10.1515\/zkri-2016-1990"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_038_w2aab3b7d169b1b6b1ab2b1c38Aa","unstructured":"L. N. F. Cardoso, T. C. M. Noguiera, C. R. Kaiser, J. L. Wardell, S. M. S. V. Wardell, M. V. N. de Souza, Z. Kristallogr. 2016, 231, 167."},{"key":"2025051309551209052_j_zkri-2018-2117_ref_039_w2aab3b7d169b1b6b1ab2b1c39Aa","doi-asserted-by":"crossref","unstructured":"L. R. Gomes, J. N. Low, A. Fonseca, M. J. Matos, F. Borges, Acta Crystallogr. 2016, E72, 926.","DOI":"10.1107\/S2056989016008665"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_040_w2aab3b7d169b1b6b1ab2b1c40Aa","doi-asserted-by":"crossref","unstructured":"L. R. Gomes, J. N. Low, A. Fonseca, M. J. Matos, F. Borges, Acta Crystallogr. 2016, E72, 1121.","DOI":"10.1107\/S2056989016011026"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_041_w2aab3b7d169b1b6b1ab2b1c41Aa","unstructured":"L.-M. Song, J.-H. Gao, Jiegou Huaxue2014, 33, 57."},{"key":"2025051309551209052_j_zkri-2018-2117_ref_042_w2aab3b7d169b1b6b1ab2b1c42Aa","unstructured":"CrysAlis PRO 1.171.39.9g: Rigaku Oxford Diffraction, 2015."},{"key":"2025051309551209052_j_zkri-2018-2117_ref_043_w2aab3b7d169b1b6b1ab2b1c43Aa","doi-asserted-by":"crossref","unstructured":"G. M. Sheldrick, Acta Crystallogr.2015, A71, 3.","DOI":"10.1107\/S2053273314026370"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_044_w2aab3b7d169b1b6b1ab2b1c44Aa","doi-asserted-by":"crossref","unstructured":"C. B. H\u00fcbschle, G. M. Sheldrick, B. Dittrich, J. Appl. Crystallogr. 2011, 44, 1281.","DOI":"10.1107\/S0021889811043202"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_045_w2aab3b7d169b1b6b1ab2b1c45Aa","doi-asserted-by":"crossref","unstructured":"G. M. Sheldrick, Crystal structure refinement with SHELXL7. Acta Crystallogr. 2015, C71, 3.","DOI":"10.1107\/S2053229614024218"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_046_w2aab3b7d169b1b6b1ab2b1c46Aa","unstructured":"Mercury, CCDC 2017."},{"key":"2025051309551209052_j_zkri-2018-2117_ref_047_w2aab3b7d169b1b6b1ab2b1c47Aa","doi-asserted-by":"crossref","unstructured":"A. L. Spek, Acta Crystallogr. 2009, D65, 148.","DOI":"10.1107\/S090744490804362X"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_048_w2aab3b7d169b1b6b1ab2b1c48Aa","doi-asserted-by":"crossref","unstructured":"A. L. Rohl, M. Moret, W. Kaminsky, K. Claborn, J. J. McKinnon, B. Kahr, Cryst. Growth Des.2008, 8, 4517.","DOI":"10.1021\/cg8005212"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_049_w2aab3b7d169b1b6b1ab2b1c49Aa","unstructured":"S. K. Wolff, D. I. Grimwood, J. J. McKinnon, M. J. Turner, D. Jayatilaka, M. A. Spackman, Crystal Explorer, The University of Western Australia, 2012."},{"key":"2025051309551209052_j_zkri-2018-2117_ref_050_w2aab3b7d169b1b6b1ab2b1c50Aa","doi-asserted-by":"crossref","unstructured":"Y. Zhao, D. G. Truhlar, Theor. Chem. Acc. 2008, 120, 215.","DOI":"10.1007\/s00214-007-0310-x"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_051_w2aab3b7d169b1b6b1ab2b1c51Aa","doi-asserted-by":"crossref","unstructured":"S. Miertus, E. Scrocco, J. Tomasi, Chem. Phys. 1981, 55, 117.","DOI":"10.1016\/0301-0104(81)85090-2"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_052_w2aab3b7d169b1b6b1ab2b1c52Aa","doi-asserted-by":"crossref","unstructured":"T. H. Dunning Jr, J. Chem. Phys. 1989, 90, 1007.","DOI":"10.1063\/1.456153"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_053_w2aab3b7d169b1b6b1ab2b1c53Aa","doi-asserted-by":"crossref","unstructured":"R. A. Kendall, T. H. Dunning Jr, R. J. Harrison, J Chem. Phys. 1992, 96, 6796.","DOI":"10.1063\/1.462569"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_054_w2aab3b7d169b1b6b1ab2b1c54Aa","unstructured":"M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, \u00d6. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09. Gaussian, Inc., Wallingford, CT, 2009."},{"key":"2025051309551209052_j_zkri-2018-2117_ref_055_w2aab3b7d169b1b6b1ab2b1c55Aa","doi-asserted-by":"crossref","unstructured":"J. Bernstein, R. E. Davis, L. Shimoni, N. L. Chang, Angew. Chem. Int. Ed. Engl.1995, 14, 1555.","DOI":"10.1002\/anie.199515551"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_056_w2aab3b7d169b1b6b1ab2b1c56Aa","doi-asserted-by":"crossref","unstructured":"C. R. Groom, I. J. Bruno, M. P. Lightfoot, S. C. Ward, Acta Crystallogr.2016, B72, 171.","DOI":"10.1107\/S2052520616003954"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_057_w2aab3b7d169b1b6b1ab2b1c57Aa","doi-asserted-by":"crossref","unstructured":"K. V. Sashidhara, M. Kumar, V. Khedgikar, P. Kushwaha, R. K. Modukuri, A. Kumar, J. Gautam, D. Singh, B. Sridhar, R. Trivedi, J. Med. Chem.2013, 56, 109.","DOI":"10.1021\/jm301281e"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_058_w2aab3b7d169b1b6b1ab2b1c58Aa","doi-asserted-by":"crossref","unstructured":"H. Takahashi, H. Takechi, K. Kubo, T. Matsumoto, Acta Crystallogr.2006, E62, o2553.","DOI":"10.1107\/S1600536806018940"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_059_w2aab3b7d169b1b6b1ab2b1c59Aa","unstructured":"V. B. Nagaveni, S. Naveen, T. O. Shrungesh Kumar, M. N. Kumara, K. M. Mahadevan, N. K. Lokanath, Der Pharma Chemica. 2016, 8, 392."},{"key":"2025051309551209052_j_zkri-2018-2117_ref_060_w2aab3b7d169b1b6b1ab2b1c60Aa","unstructured":"Y.-F. Sun, S.-Y. Ma, D. Zhang, X.-L. Cheng, Yi.-X Kexue, Yu Guang Huaxue2008, 26, 393."},{"key":"2025051309551209052_j_zkri-2018-2117_ref_061_w2aab3b7d169b1b6b1ab2b1c61Aa","doi-asserted-by":"crossref","unstructured":"C.-L. Xu, S.-Y. Liu, C.-X. Wang, M.-Q. Zhao, Acta Crystallogr.2009, E65, o2817.","DOI":"10.1107\/S1600536809041725"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_062_w2aab3b7d169b1b6b1ab2b1c62Aa","doi-asserted-by":"crossref","unstructured":"H. Moon, Q. P. Xuan, D. Kim, Y. Kim, J. W. Park, Cryst. Growth Des. 2014, 14, 6613.","DOI":"10.1021\/cg501567s"},{"key":"2025051309551209052_j_zkri-2018-2117_ref_063_w2aab3b7d169b1b6b1ab2b1c63Aa","doi-asserted-by":"crossref","unstructured":"L.-C. Lo, J.-Y. Chen, C.-T. Yang, D.-S. Gu, Chirality2001, 13, 266.","DOI":"10.1002\/chir.1029"}],"container-title":["Zeitschrift f\u00fcr Kristallographie - Crystalline Materials"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/www.degruyter.com\/view\/j\/zkri.2019.234.issue-2\/zkri-2018-2117\/zkri-2018-2117.xml","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.degruyterbrill.com\/document\/doi\/10.1515\/zkri-2018-2117\/xml","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.degruyterbrill.com\/document\/doi\/10.1515\/zkri-2018-2117\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,5,13]],"date-time":"2025-05-13T09:56:02Z","timestamp":1747130162000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.degruyterbrill.com\/document\/doi\/10.1515\/zkri-2018-2117\/html"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,1,24]]},"references-count":63,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2019,1,24]]},"published-print":{"date-parts":[[2019,2,25]]}},"alternative-id":["10.1515\/zkri-2018-2117"],"URL":"https:\/\/doi.org\/10.1515\/zkri-2018-2117","relation":{},"ISSN":["2196-7105","2194-4946"],"issn-type":[{"value":"2196-7105","type":"electronic"},{"value":"2194-4946","type":"print"}],"subject":[],"published":{"date-parts":[[2019,1,24]]}}}