DOI: 10.1002/jcc.540140406. Prediction of possible crystal structures for C‐, H‐, N‐, O‐, and F‐containing organic compounds

Prediction of possible crystal structures for C‐, H‐, N‐, O‐, and F‐containing organic compounds

10.1002/jcc.540140406

Crossref journal-article

Wiley

Journal of Computational Chemistry (311)

Abstract

AbstractA procedure is reported for the prediction of dense crystal structures of C‐, H‐, N‐, O‐, and F‐containing organic compounds in the primitive triclinic, monoclinic, and orthorhombic space groups with Z ≤ 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‐body 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‐D map of minimum unit cell volume as a function of the orientation of the central molecule. MOLPAK uses a repulsion‐only potential and a preset threshold to place molecules in contact with each other. The 5–10 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, P21, P21/c, and P212121 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. © 1993 John Wiley & Sons, Inc.

Bibliography

Holden, J. R., Du, Z., & Ammon, H. L. (1993). Prediction of possible crystal structures for Câ, Hâ, Nâ, Oâ, and Fâcontaining organic compounds. Journal of Computational Chemistry, 14(4), 422â437. Portico.

Authors 3

James R. Holden (first)
Zuyue Du (additional)
Herman L. Ammon (additional)

References 38 Referenced 186

J.R.HoldenandC.Dickinson Prediction of Crystal Density through Molecular Packing Analysis Report NSWC MP 79‐185 Naval Surface Weapons Center Silver Spring MD 1979.
D.T.Cromer H.L.Ammon andJ.R.Holden A Procedure of Estimating the Crystal Densities of Organic Explosives Report LA‐11142‐MS Los Alamos Scientific Laboratory Los Alamos NM 1987.
10.1080/07370658408012329
10.1063/1.1667908
(a)H.H.Cady Estimation of the Densities of Organic Explosives from Their Structural Formulas Report LA‐7760‐MS Los Alamos Scientific Laboratory Los Alamos NM 1979;
10.1021/je60081a006
10.1107/S0567739477000448
(d)D.A.Cichra J.R.Holden andC.Dickinson Estimation of Normal Densities of Explosive Compounds from Empirical Atomic Volumes Report 79‐273 Naval Surface Weapons Center Silver Spring MD 1980;
(e)J.R.Stine Prediction of Crystal Densities of Organic Explosives by Group Additivity Report LA‐8920 Los Alamos National Laboratory Los Alamos NM 1981. (10.2172/6254123)
10.1107/S0567740872007046
10.1107/S0365110X63001651
10.1007/BF00955829 / Bull. Acad. Sci. USSR, Div. Chem. Sci. by Zhitomirskaya N.G. (1987)
10.1021/ja00012a034
W.R.Busing WMIN A Computer Program to Model Molecules and Crystals in Terms of Potential Energy Functions Report ORNL‐5747 Oak Ridge National Laboratory Oak Ridge TN 1981. (10.2172/6572983)
Cambridge Structural Database v. 4.6 Cambridge Crystallographic Data Center Cambridge UK 1992.
{'key': 'e_1_2_1_13_2', 'volume-title': 'Molecular Crystals and Molecules', 'author': 'Kitaigorodsky A.I.', 'year': '1973'} / Molecular Crystals and Molecules by Kitaigorodsky A.I. (1973)
{'key': 'e_1_2_1_14_2', 'first-page': '260', 'volume-title': 'The Nature of the Chemical Bond', 'author': 'Pauling L.', 'year': '1960'} / The Nature of the Chemical Bond by Pauling L. (1960)
10.1107/S0567740872004455 / Acta Cryst. by Baur W.H. (1973)
10.1021/j100785a001
10.1021/ci00049a002
10.1107/S0108768191011977
10.1038/222339a0
10.1021/j100530a018
{'key': 'e_1_2_1_18_2', 'first-page': '169', 'volume-title': 'Computing in Crystallography', 'author': 'Mirsky K.', 'year': '1978'} / Computing in Crystallography by Mirsky K. (1978)
10.1107/S0567739477001910 / Acta Cryst. by Starr T.L. (1977)
10.1107/S0567739481000703
10.1002/jcc.540020312
{'key': 'e_1_2_1_21_2', 'first-page': '95', 'volume-title': 'Tenth Annual Working Group Institute on the Synthesis of High Energy Density Materials', 'author': 'Kober E.', 'year': '1991'} / Tenth Annual Working Group Institute on the Synthesis of High Energy Density Materials by Kober E. (1991)
J.P.Ritchie E.M.Kober andA.S.Copenhaver unpublished.
{'key': 'e_1_2_1_22_2', 'volume-title': 'Macromodel, Columbia Chemisry Molecular Modeling System', 'author': 'Still C.', 'year': '1990'} / Macromodel, Columbia Chemisry Molecular Modeling System by Still C. (1990)
10.1021/ja00299a024
{'key': 'e_1_2_1_23_3', 'volume-title': 'MOPAC, A General Molecular Orbital Package', 'author': 'Stewart J.J.P.', 'year': '1990'} / MOPAC, A General Molecular Orbital Package by Stewart J.J.P. (1990)
{'key': 'e_1_2_1_24_2', 'volume-title': 'A Program to Analyze Lattice Relationships', 'author': 'Karen V.L.', 'year': '1991'} / A Program to Analyze Lattice Relationships by Karen V.L. (1991)
10.1107/S0567740874002603
10.1103/PhysRevB.38.1058 / Phys. Rev. by Kunz A.B. (1988)
10.1002/qua.560382459
{'key': 'e_1_2_1_26_4', 'author': 'Kunz A.B.', 'journal-title': 'Theor Chem. Acta'} / Theor Chem. Acta by Kunz A.B.
{'key': 'e_1_2_1_27_2', 'volume-title': 'Chem3D, the Molecular Modeling System', 'year': '1990'} / Chem3D, the Molecular Modeling System (1990)

Dates

Type	When
Created	20 years, 7 months ago (Jan. 1, 2005, 8 p.m.)
Deposited	1 year, 9 months ago (Oct. 26, 2023, 2:34 a.m.)
Indexed	2 weeks, 3 days ago (Aug. 5, 2025, 8:37 a.m.)
Issued	32 years, 4 months ago (April 1, 1993)
Published	32 years, 4 months ago (April 1, 1993)
Published Online	20 years, 11 months ago (Sept. 7, 2004)
Published Print	32 years, 4 months ago (April 1, 1993)

Funders 0

None

BibTeX

@article{Holden_1993, title={Prediction of possible crystal structures for C‐, H‐, N‐, O‐, and F‐containing organic compounds}, volume={14}, ISSN={1096-987X}, url={http://dx.doi.org/10.1002/jcc.540140406}, DOI={10.1002/jcc.540140406}, number={4}, journal={Journal of Computational Chemistry}, publisher={Wiley}, author={Holden, James R. and Du, Zuyue and Ammon, Herman L.}, year={1993}, month=apr, pages={422–437} }

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