In situ crystallization and crystal structure determination of chlorobenzene

Naba K. Nath, Panče Naumov

Abstract


The crystal structure of chlorobenzene, which is liquid at ambient conditions of pressure and temperature, was determined after in situ crystallization by using Optical Heating and Crystallization Device (OHCD) coupled to a single crystal X-ray diffractometer. Chlorobenzene crystallizes in the orthorhombic space group Pbcn with one symmetry-independent molecule in the asymmetric unit. In the crystal structure, type II ClCl interactions form zigzag chains that are assisted by C—Hπ interactions. Hirshfeld surface analysis revealed five types of intermolecular contacts.


Keywords


Optical Heating and Crystallization Device; chlorobenzene; X-ray diffraction

Full Text:

PDF

References


R. Boese, Special issue on In Situ Crystallization, Z. Kristallogr., 229, 595−601 (2014).

D. Brodalla, D. Mootz, R. Boese, W. Osswald, J. Appl. Cryst., 18, 316−319 (1985).

D. Šišak, L. B. McCusker, G. Zandomeneghi, B. H. Meier, D. Bläser, R. Boese, W. B. Schweizer, R. Gilmour, J. D. Dunitz, The Crystal Structure of D-Ribose—At Last!, Angew. Chem. Int. Ed., 49, 4503–4505 (2010).

R. Boese, D. Bläser, G. Jansen, Synthesis and Theoretical Characterization of an Acetylene-Ammonia Cocrystal, J. Am. Chem. Soc., 131, 2104–2106 (2009).

R. Boese, D. Bläser, K. Gomann, U. H. Brinker, Spiropentane as a Tensile Spring, J. Am. Chem. Soc., 111, 1501–1503 (1989).

R. Neidlein, D. Christen, V. Poignée, R. Boese, D. Bläser, A. Gieren, C. Ruiz-Pérez, T. Hübner, The Structures of 1H-Cyclopropabenzene and Its 1,l-Bis(triisopropylsily1) Derivative, Angew. Chem. Int. Ed. Engl., 27, 294–295 (1988).

K. K. Baldridge, B. Biggs, D. Bläser, R. Boese, R. D. Gilbertson, M. M. Haley, A. H. Maulitz, J. S. Siegel, X-Ray crystal and ab initio structure of 3-ethynylcyclopropene: a curiously short carbon–carbon double bond, Chem. Commun., 1137–1138 (1998).

R. Boese, T. Clark, A. Gavezzotti, Cocrystallization with Acetylene. The 1:1 Complex with Benzene: Crystal Growth, X-Ray Diffraction and Molecular Simulations, Helv. Chim. Acta, 86, 1085–1100 (2003).

M.T. Kirchner, R. Boese, W.E. Billups, L. R. Norman, Gas Hydrate Single-Crystal Structure Analyses, J. Am. Chem. Soc., 126, 9407–9412 (2004).

S. Crawford, M. T. Kirchner, D. Bläser, R. Boese, W. I. F. David, A. Dawson, A. Gehrke, R. M. Ibberson, W. G. Marshall, S. Parsons, O. Yamamuro, Isotopic Polymorphism in Pyridine, Angew. Chem. Int. Ed., 48, 755–757 (2009).

S. G. Biswas, Crystal Structure of Chlorobenzene and Bromobenzene at −180 °C, Acta Cryst., 11, 882–884 (1958).

P. D. Andre, R. Fourme, M. Renaud, Structure Cristalline du Monochlorobenzène à 393 K et 14,2 kbars: Un Affinement par Groupe Rigide, Acta Cryst. B, 27, 2371–2380 (1971).

R. Boese, M. T. Kirchner, J. D. Dunitz, G. Filippini, A. Gavezzotti, Solid-State Behaviour of the Dichlorobenzenes: Actual, Semi-Virtual and Virtual Crystallography, Helv. Chim. Acta, 84, 1561–1577 (2001).

M. Bujak, K. Dziubek, A. Katrusiak, Halogenhalogen interactions in pressure-frozen ortho- and meta-dichlorobenzene isomers, Acta Cryst. B, 63, 124–131 (2007).

U. Croatto, S. Bezzi, E. Bua, The Crystal Structure of p-Dichlorobenzene, Acta Cryst., 5, 825–829 (1952).

E. Estop, A. Alvarez-Larena, A. Belaaraj, X. Solans, M. Labrador, α-Phase p-Dichlorobenzene at 293 K, Acta Cryst. C, 53, 1932–1935 (1997).

P. J. Housty, J. Clastre, Structure Cristalline de la Forme Triclinique du Para-dichlorobenzène, Acta Cryst., 10, 695–698 (1957).

G. L. Wheeler, S. D. Colson, γ-Phase p-Dichlorobenzene at 100 K, Acta Cryst. B, 31, 911–913 (1975).

G. L. Wheeler, S. D. Colson, Intermolecular interactions in polymorphic p-dichlorobenzene crystals: The α, β, and γ phases at 100 K, J. Chem. Phys., 65, 1227–1235 (1976).

K. Merz, Substitution Effect on Crystal Packings of Iodobenzonitriles and Iodophenols, Cryst. Growth Des., 6, 1615–1619 (2006).

M. A. Spackman, D. Jayatilaka, Hirshfeld surface analysis, CrystEngComm, 11, 19–32 (2009).

J. J. McKinnon, D. Jayatilaka, M. A. Spackman, Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces, Chem. Commun., 3814–3816 (2007).

J. J. McKinnon, M. A. Spackman, A. S. Mitchell, Novel tools for visualizing and exploring intermolecular interactions in molecular crystals, Acta Cryst. B, 60, 627–668 (2004).

APEX DUO, version 2.1-4, and SAINT, version 7.34A; Bruker AXS Inc.: Madison, WI, 2012.

G. M. Sheldrick, SADABS, University of Göttingen, Göttingen, Germany, 1996.

G. M. Sheldrick, Acta Cryst. A, 64, 112–122 (2008).

G. M. Sheldrick, SHELXL2014, University of Göttingen, Göttingen, Germany, 1996.

CrystalExplorer (Version 3.1), S. K. Wolff, D. J. Grimwood, J. J. McKinnon, M. J. Turner, D. Jayatilaka, M. A. Spackman, University of Western Australia, 2012.




DOI: http://dx.doi.org/10.20450/mjcce.2015.682

Refbacks

  • There are currently no refbacks.




Copyright (c) 2016 Naba K. Nath, Panče Naumov

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.