In situ crystallization of the linear alkynes Cn H2n–2 (n=7, 8, 9, 10)
-
Andrew D. Bond
and
John E. Davies
Abstract
A manual in situ crystallization technique is described, for application on a κ-geometry area-detector instrument. The technique has been applied to grow crystals of some linear alkynes: 1-heptyne, 1-octyne, 1-nonyne and 1-decyne, Cn H2n–2 (n=7, 8, 9, 10). The structures with odd n (1-heptyne and 1-nonyne) crystallize in space group Pca21. The structures with even n (1-octyne and 1-decyne) crystallize in space group P21/c, with two molecules in the asymmetric unit (Z′=2) and an approximately orthorhombic metric. All of the structures contain layers of molecules with a square unit mesh of dimensions 5.7×7.2 Å, identical to the layers present in the previously published structures of 1,7-octadiyne and 1,9-decadiyne. The structures differ where the methyl groups meet, giving systematically greater packing efficiency for 1-heptyne and 1-nonyne, compared to 1-octyne and 1-decyne. This systematic alternation in crystal density is correlated with an alternation in melting points.
References
[1] R. Rudman, Low-Temperature X-Ray Diffraction, Plenum Press, New York, 1976.10.1007/978-1-4615-8771-2Search in Google Scholar
[2] R. Boese, M. Nussbaumer, “In situ crystallization techniques”, in Organic Crystal Chemistry, (Ed. D. W. Jones) Oxford University Press, Oxford, pp. 20–37, 1994.Search in Google Scholar
[3] A. D. Bond, J. E. Davies, Acta Cryst.2001, E57, o1191.Search in Google Scholar
[4] A. D. Bond, J. E. Davies, Aust. J. Chem.2001, 54, 683.Search in Google Scholar
[5] A. D. Bond, J. E. Davies, Acta Cryst.2001, E57, o947.Search in Google Scholar
[6] A. D. Bond, J. E. Davies, Acta Cryst.2002, E58, o196.Search in Google Scholar
[7] R. Boese, H.-Ch. Weiss, D. Bläser, Angew. Chem. Int Ed., 1999, 38, 988.10.1002/(SICI)1521-3773(19990401)38:7<988::AID-ANIE988>3.0.CO;2-0Search in Google Scholar
[8] V. R. Thalladi, R. Boese, H.-Ch. Weiss, Angew. Chem. Int. Ed., 2000, 39, 918.10.1002/(SICI)1521-3773(20000303)39:5<918::AID-ANIE918>3.0.CO;2-ESearch in Google Scholar
[9] V. R. Thalladi, R. Boese, H.-Ch. Weiss, J. Am. Chem. Soc.2000, 122, 1186.Search in Google Scholar
[10] V. R. Thalladi, M. Nüsse, R. Boese, J. Am. Chem. Soc.2000, 122, 9227.Search in Google Scholar
[11] A. D. Bond, New J. Chem.2004, 28, 104.Search in Google Scholar
[12] A. D. Bond, Chem. Comm.2002, 1664.10.1039/B204261DSearch in Google Scholar
[13] I. T. Sugawara, E. Kanda, Sci. Rep. Res. Inst. Tohoku Univ. Series A,1952, 607.Search in Google Scholar
[14] G. J. H. van Nes, F. van Bolhuis, Acta Cryst.1979, B35, 2580.Search in Google Scholar
[15] R. K. McMullan, Å. Kvick, P. Popelier, Acta Cryst.1992, B48, 726.Search in Google Scholar
[16] F. H. Allen, Acta Cryst.2002, B58, 380.Search in Google Scholar
[17] G. J. H. Van Nes, F. Van Bolhuis, J. Appl. Cryst.1978, 11, 206.Search in Google Scholar
[18] J. D. Dunitz, A. Gavezzotti, Acc. Chem. Res.1999, 32, 677.Search in Google Scholar
[19] J. Wei, Ind. Eng. Chem. Res.1999, 38, 5019.Search in Google Scholar
©2014 by De Gruyter
Articles in the same Issue
- Frontmatter
- Graphical Synopsis
- Preface
- Special issue on In Situ Crystallization
- Original Papers
- Crystal architecture of the low melting nitrogen heterocycles tetrafluoropyrimidine and trifluorotriazine
- Fluorine prefers hydrogen bonds over halogen bonds! Insights from crystal structures of some halofluorobenzenes
- In situ co-crystallization of cresols with aniline and fluoroanilines: subtle interplay of strong and weak hydrogen bonds
- In situ Crystallization of N(SiMe3)3 and As(SiMe3)3: Trigonal planar or pyramidal coordination of the central atoms?
- Low-melting molecular complexes. Part 5. Co-crystals of tetrahydrofuran and diethyl ether with methyl halides
- Comparison of intermolecular interactions in two phases of MeNSOF2
- In situ crystallization of the linear alkynes Cn H2n–2 (n=7, 8, 9, 10)
- A high-pressure polymorph of propionamide from in situ high-pressure crystallisation from solution
Articles in the same Issue
- Frontmatter
- Graphical Synopsis
- Preface
- Special issue on In Situ Crystallization
- Original Papers
- Crystal architecture of the low melting nitrogen heterocycles tetrafluoropyrimidine and trifluorotriazine
- Fluorine prefers hydrogen bonds over halogen bonds! Insights from crystal structures of some halofluorobenzenes
- In situ co-crystallization of cresols with aniline and fluoroanilines: subtle interplay of strong and weak hydrogen bonds
- In situ Crystallization of N(SiMe3)3 and As(SiMe3)3: Trigonal planar or pyramidal coordination of the central atoms?
- Low-melting molecular complexes. Part 5. Co-crystals of tetrahydrofuran and diethyl ether with methyl halides
- Comparison of intermolecular interactions in two phases of MeNSOF2
- In situ crystallization of the linear alkynes Cn H2n–2 (n=7, 8, 9, 10)
- A high-pressure polymorph of propionamide from in situ high-pressure crystallisation from solution
