Pöppler, Ann Christin, Corletta, Emily K., Pearce, Harriet, Seymour, Mark, Reid, Matthew M., Montgomery, Mark G. and Brown, Steven P. (2017) Single-crystal X-ray diffraction and NMR crystallography of a 1:1 cocrystal of dithianon and pyrimethanil. Acta Crystallographica Section C : Structural Chemistry, C73 (3). pp. 149-156. doi:10.1107/S2053229617000870 ISSN 2053-2296.

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Abstract

A single-crystal X-ray diffraction structure of a 1:1 cocrystal of two fungicides, namely di­thia­non (DI) and pyrimethanil (PM), is reported [systematic name: 5,10-dioxo-5H,10H-naphtho­[2,3-b][1,4]dithiine-2,3-dicarbo­nitrile–4,6-dimethyl-N-phenyl­pyrimidin-2-amine (1/1), C14H4N2O2S2·C12H13N2]. Following an NMR crystallography approach, experimental solid-state magic angle spinning (MAS) NMR spectra are presented together with GIPAW (gauge-including projector augmented wave) calculations of NMR chemical shieldings. Specifically, experimental 1H and 13C chemical shifts are determined from two-dimensional 1H–13C MAS NMR correlation spectra recorded with short and longer contact times so as to probe one-bond C—H connectivities and longer-range C...H proximities, whereas H...H proximities are identified in a 1H double-quantum (DQ) MAS NMR spectrum. The performing of separate GIPAW calculations for the full periodic crystal structure and for isolated mol­ecules allows the determination of the change in chemical shift upon going from an isolated mol­ecule to the full crystal structure. For the 1H NMR chemical shifts, changes of 3.6 and 2.0 ppm correspond to inter­molecular N—H...O and C—H...O hydrogen bonding, while changes of −2.7 and −1.5 ppm are due to ring current effects associated with C—H...π inter­actions. Even though there is a close inter­molecular S...O distance of 3.10 Å, it is of note that the mol­ecule-to-crystal chemical shifts for the involved sulfur or oxygen nuclei are small.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry S Agriculture > S Agriculture (General)
Divisions:	Faculty of Science, Engineering and Medicine > Science > Chemistry Faculty of Science, Engineering and Medicine > Research Centres > Molecular Organisation and Assembly in Cells (MOAC) Faculty of Science, Engineering and Medicine > Science > Physics
Library of Congress Subject Headings (LCSH):	Agricultural chemicals
Journal or Publication Title:	Acta Crystallographica Section C : Structural Chemistry
Publisher:	Wiley
ISSN:	2053-2296
Official Date:	1 March 2017
Dates:	Date Event 17 January 2017 Accepted 1 March 2017 Published
Volume:	C73
Number:	3
Page Range:	pp. 149-156
DOI:	10.1107/S2053229617000870
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Open Access (Creative Commons)
Date of first compliant deposit:	26 January 2017
Date of first compliant Open Access:	30 March 2017
RIOXX Funder/Project Grant:	Project/Grant ID RIOXX Funder Name Funder ID UNSPECIFIED Alexander von Humboldt-Stiftung http://dx.doi.org/10.13039/100005156 UNSPECIFIED Royal Society http://dx.doi.org/10.13039/501100000288 EP/L015307/1 [EPSRC] Engineering and Physical Sciences Research Council http://dx.doi.org/10.13039/501100000266 EP/K000128/1 [EPSRC] Engineering and Physical Sciences Research Council http://dx.doi.org/10.13039/501100000266 639907 Seventh Framework Programme http://dx.doi.org/10.13039/100011102
Related URLs:	Related dataset

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