Abstract
The structure of trans-1,4-dibromo-1,4-dicarboxymethylcyclohexane (I) has been determined by single crystal x-ray diffraction. The molecules, located on symmetry centers, are in the rigid chair conformation with the Br and COOCH3 axial and equatorial, respectively. The molecular geometry observed in the crystal is similar to that calculated for the isolated molecule using ab initio calculations performed at the HF/6-31(d) level. A peculiar arrangement of the carboxymethyl substituents, along with short contacts involving the Br atoms, seem to play a role in the stabilization of the crystalline structure.
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Bürgi, H.; Dunitz, J. D. Structure Correlation, VCH: Weinheim, 1994.
Lommerse, J. P. M.; Stone, A. J.; Taylor, R. Y.; Allen, F. H. J. Am. Chem. Soc. 1996, 118, 3108–3116.
Desiraju, G. R. J. Chem. Soc. Chem. Comm. 1997, 1475–1482.
Echeverría, G.; Punte, G.; Rivero, B. E.; Barón, M. Acta Cryst. 1995a, C51, 1023–1026.
Echeverría, G.; Punte, G.; Rivero, B. E.; Barón, M. Acta Cryst. 1995a, C51, 1023–1026.
Barón, M.; de Zenobi, E. L.; Davidson, M. J. Mol. Struct. 1975, 124, 432–438.
Enraf-Nonius. CAD-4-PC. Version 1.2; Enraf-Nonius: Delft, The Netherlands, 1993.
Fair, C. K. MolEN Version 1.0. Enraf-Nonius Structure. Determination System; Enraf-Nonius: Delft, The Netherlands, 1990.
Sheldrick, G. M. SHELXS86. Program for the solution of crystal structures; University of Göttingen, Germany, 1985.
Sheldrick, G. M. SHELXL93. Program for the Refinement of Crystal Structures; University of Göttingen, Germany, 1993.
Spek, A. L. Acta Cryst. 1990, C34, A46.
Nardelli, M. Computer Chemistry PARST, 1983, 7, 95–98.
Johnson, C. K. ORTEPII, Report ORNL-5138, Oak Ridge National Laboratory, Tennesse, 1976.
Allen, F. H.; Davies, J. E.; Galloy, J. J.; Johnson, O.; Kennard, O.; Macrae, C. F.; Mitchell, E. M.; Mitchell, G. F.; Smith, J. M.; Watson, D. G. J. Chem. Inf. Comput. Sci. 1991, 31, 187–204.
Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision B.3; Gaussian, Inc.: Pittsburgh PA, 1995.
Bucourt, R.; Hainaut, D. Soc. Chim. 1965, 5, 1366–1378.
Dunitz, J. D.; Strickler, P. Helv. Chim. Acta 1966, 8, 290–291.
Von Luger, P.; Plieth, K.; Ruban, G. Acta Cryst. 1972, B28, 706–710.
Cremer, D.; Pople, I. J. Am. Chem. Soc. 1975, 97, 1354–1358.
Dommen, J.; Brupbacher, Th.; Grassi, G.; Bauder, A. J. Am. Chem. Soc. 1990, 12, 953.
Swenson, D. C.; Davis, C. R.; Burton, D. J. Acta Cryst. 1996, C52, 2844–2847.
Goodhand, N.; Hamor, T. A. Acta Cryst. 1978, B34, 513–516.
Hassel, G.; Handler Vihovde, E. Acta Chem. Scand. 1953, H7, 1164–1169.
Cremer, D.; Szabo, K. J. In Conformational Behaviour of Six Membered Rings; Juaristi, E., Ed.; VCH: Weinheim, New York, 1995.
Ciolowski, J.; Edgington, L.; Stefanov, B. B. J. Am. Chem. Soc. 1995, 117, 10381–10384.
Bondi, A. J. Phys. Chem. 1964, 68, 441–451.
Leiserowitz, L., Acta Cryst. 1976, B32, 775–802.
Cambridge Structural Database. Version 5.13 Cambridge Crystallographic Data Centre; Cambridge, 1997.
Desiraju, G. R. Crystal Engineering; Elsevier Science Publishers B. V.: Amsterdam, 1989.
Sakurai, T.; Sundaramlingam, J. T.; Jeffrey, G. A. Acta Cryst. 1963, 16, 354.
Patil, A. A.; Curtin, D. Y.; Paul, I. C. Isr. J. Chem. 1985, 25, 320–326.
Pedireddi, V. R.; Reddy, D. S.; Goud, B. S.; Craig, D. C.; Rae, A. D. J. Chem. Soc. Perkin Trans 1994, 2, 2353–2360.
Price, S. L.; Stone, A. J.; Lucas, J.; Rowland, R. S.; Thornley, A. E. J. Am. Chem. Soc. 1994, 116, 4910–4918.
Allen, F. H.; Baalham, C. A.; Lommerse, J. P.; Raithby, P. R. Acta Cryst. 1998, B54, 320–329.
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Echeverría, G.A., Barón, M. & Punte, G. Ab Initio and in-Crystal Geometry of trans-1,4-Dibromo1,4-dicarboxymethylcyclohexane. Structural Chemistry 11, 35–40 (2000). https://doi.org/10.1023/A:1009216305908
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DOI: https://doi.org/10.1023/A:1009216305908