2,3-Dichloro-1,4-hydroquinone 2,3-dichloro-1,4-benzoquinone monohydrate: a quinhydrone-type 1:1 donor-acceptor [D-A] charge-transfer complex

Guegano, Xavier; Hauser, Jürg; Liu, Shi-Xia; Decurtins, Silvio (2011). 2,3-Dichloro-1,4-hydroquinone 2,3-dichloro-1,4-benzoquinone monohydrate: a quinhydrone-type 1:1 donor-acceptor [D-A] charge-transfer complex. Acta crystallographica. Section E - Structure reports online, 67(11), O2967-O2968. Copenhagen: Munksgaard 10.1107/S1600536811041377

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In the crystal structure of the title compound (systematic name: 2,3-dichlorobenzene-1,4-diol 2,3-dichlorocyclohexa-2,5-diene-1,4-dione monohydrate), C(6)H(4)Cl(2)O(2)center dot C(6)H(2)Cl(2)O(2)center dot H(2)O, the 2,3-dichloro-1,4-hydroquinone donor (D) and the 2,3-dichloro-1,4-benzoquinone acceptor (A) molecules form alternating stacks along [100]. Their molecular planes [maximum deviations for non-H atoms: 0.0133 (14) (D) and 0.0763 (14) angstrom (A)] are inclined to one another by 1.45 (3)degrees and are thus almost parallel. There are pi-pi interactions involving the D and A molecules, with centroid-centroid distances of 3.5043 (9) and 3.9548 (9) angstrom. Intermolecular O-H center dot center dot center dot O hydrogen bonds involving the water molecule and the hydroxy and ketone groups lead to the formation of two-dimensional networks lying parallel to (001). These networks are linked by C-H center dot center dot center dot O interactions, forming a three-dimensional structure.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Hauser, Jürg; Liu, Shi-Xia and Decurtins, Silvio

ISSN:

1600-5368

Publisher:

Munksgaard

Language:

English

Submitter:

Factscience Import

Date Deposited:

04 Oct 2013 14:26

Last Modified:

06 Dec 2013 13:31

Publisher DOI:

10.1107/S1600536811041377

Web of Science ID:

000297859000061

URI:

https://boris.unibe.ch/id/eprint/9397 (FactScience: 215128)

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