{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,26]],"date-time":"2026-02-26T22:20:00Z","timestamp":1772144400040,"version":"3.50.1"},"reference-count":38,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2004,9,7]],"date-time":"2004-09-07T00:00:00Z","timestamp":1094515200000},"content-version":"vor","delay-in-days":4177,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J Comput Chem"],"published-print":{"date-parts":[[1993,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A procedure is reported for the prediction of dense crystal structures of C\u2010, H\u2010, N\u2010, O\u2010, and F\u2010containing organic compounds in the primitive triclinic, monoclinic, and orthorhombic space groups with Z \u2264 4. The crystal environments of molecules in 242 crystal structures have been analyzed to determine the common coordination sphere pattens. This led to the development of the MOLPAK (MOLecular PAcKing) program, which uses a rigid\u2010body molecular structure probe to build packing arrangements (possible crystal structures) in the various space groups. A MOLPAK search, which involves the investigation of all unique orientations of a central molecule and the construction of the appropriate coordination patterns about the central molecule, provides a 3\u2010D map of minimum unit cell volume as a function of the orientation of the central molecule. MOLPAK uses a repulsion\u2010only potential and a preset threshold to place molecules in contact with each other. The 5\u201310 smallest volume packing arrangements from a search are subjected to a lattice energy minimization refinement with the WMIN program to yield possible crystal structures. The results are described from the analyses of several known compounds starting with the crystal molecular structures as the MOLPAK search probes in the P1, P2<jats:sub>1<\/jats:sub>, P2<jats:sub>1<\/jats:sub>\/c, and P2<jats:sub>1<\/jats:sub>2<jats:sub>1<\/jats:sub>2<jats:sub>1<\/jats:sub> space groups. In addition, several examples are given in which the search probes were created by AM1 geometry optimization of preliminary molecular models. More extensive data are given in supplementary tables. \u00a9 1993 John Wiley &amp; Sons, Inc.<\/jats:p>","DOI":"10.1002\/jcc.540140406","type":"journal-article","created":{"date-parts":[[2005,1,2]],"date-time":"2005-01-02T01:00:06Z","timestamp":1104627606000},"page":"422-437","source":"Crossref","is-referenced-by-count":193,"title":["Prediction of possible crystal structures for C\u2010, H\u2010, N\u2010, O\u2010, and F\u2010containing organic compounds"],"prefix":"10.1002","volume":"14","author":[{"given":"James R.","family":"Holden","sequence":"first","affiliation":[]},{"given":"Zuyue","family":"Du","sequence":"additional","affiliation":[]},{"given":"Herman L.","family":"Ammon","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2004,9,7]]},"reference":[{"key":"e_1_2_1_2_2","unstructured":"J.R.HoldenandC.Dickinson Prediction of Crystal Density through Molecular Packing Analysis Report NSWC MP 79\u2010185 Naval Surface Weapons Center Silver Spring MD 1979."},{"key":"e_1_2_1_3_2","unstructured":"D.T.Cromer H.L.Ammon andJ.R.Holden A Procedure of Estimating the Crystal Densities of Organic Explosives Report LA\u201011142\u2010MS Los Alamos Scientific Laboratory Los Alamos NM 1987."},{"key":"e_1_2_1_4_2","doi-asserted-by":"publisher","DOI":"10.1080\/07370658408012329"},{"key":"e_1_2_1_5_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.1667908"},{"key":"e_1_2_1_6_2","unstructured":"(a)H.H.Cady Estimation of the Densities of Organic Explosives from Their Structural Formulas Report LA\u20107760\u2010MS Los Alamos Scientific Laboratory Los Alamos NM 1979;"},{"key":"e_1_2_1_6_3","doi-asserted-by":"publisher","DOI":"10.1021\/je60081a006"},{"key":"e_1_2_1_6_4","doi-asserted-by":"publisher","DOI":"10.1107\/S0567739477000448"},{"key":"e_1_2_1_6_5","unstructured":"(d)D.A.Cichra J.R.Holden andC.Dickinson Estimation of Normal Densities of Explosive Compounds from Empirical Atomic Volumes Report 79\u2010273 Naval Surface Weapons Center Silver Spring MD 1980;"},{"key":"e_1_2_1_6_6","doi-asserted-by":"crossref","unstructured":"(e)J.R.Stine Prediction of Crystal Densities of Organic Explosives by Group Additivity Report LA\u20108920 Los Alamos National Laboratory Los Alamos NM 1981.","DOI":"10.2172\/6254123"},{"key":"e_1_2_1_7_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0567740872007046"},{"key":"e_1_2_1_8_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0365110X63001651"},{"key":"e_1_2_1_9_2","doi-asserted-by":"crossref","first-page":"525","DOI":"10.1007\/BF00955829","volume":"36","author":"Zhitomirskaya N.G.","year":"1987","journal-title":"Bull. 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