Solid state structure and hydrogen bonding of some cyclic NH carboximides

R Alan Aitken; Alexander J B Nelson; Alexandra M .Z. Slawin; Dheirya K. Sonecha

doi:10.3390/cryst13010150

Solid state structure and hydrogen bonding of some cyclic NH carboximides

R Alan Aitken^*, Alexander J B Nelson, Alexandra M .Z. Slawin, Dheirya K. Sonecha

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

Thirteen new crystal structures of cyclic NH carboximides have been determined and are compared with respect to the mode of intermolecular hydrogen bonding observed in the crystal. The structures include a new cyclobutane-fused succinimide, seven new simple bi- and tricyclic succinimides derived from Diels-Alder reactions of maleimide, three methylated glutarimides, a morpholinedione and adipimide, the first seven-membered ring NH carboximide to be structurally characterised. Overall seven of the compounds adopt a ribbon structure, five show centro-symmetric dimers, and one has bonding between NH and a remote bridging ether oxygen. Halogen bonding was also detected in one case.

Original language	English
Article number	150
Number of pages	10
Journal	Crystals
Volume	13
Issue number	1
DOIs	https://doi.org/10.3390/cryst13010150
Publication status	Published - 15 Jan 2023

Keywords

Hydrogen bonding
Dimer
Ribbon
Succinimide
Glutarimide
Halogen bonding

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10.3390/cryst13010150Licence: CC BY

Aitken_2023_Crystals_Hydrogenbonding_CC
Copyright: © 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0).
Final published version, 859 KBLicence: CC BY

CCDC 2225704-2225716: Experimental Crystal Structure Determination
Aitken, R. A. (Creator), Nelson, A. J. B. (Creator), Slawin, A. M. Z. (Creator) & Sonecha, D. K. (Creator), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc2dq0x2, https://dx.doi.org/10.5517/ccdc.csd.cc2dq0y3 and 11 more links, https://dx.doi.org/10.5517/ccdc.csd.cc2dq0z4, https://dx.doi.org/10.5517/ccdc.csd.cc2dq106, https://dx.doi.org/10.5517/ccdc.csd.cc2dq117, https://dx.doi.org/10.5517/ccdc.csd.cc2dq128, https://dx.doi.org/10.5517/ccdc.csd.cc2dq139, https://dx.doi.org/10.5517/ccdc.csd.cc2dq14b, https://dx.doi.org/10.5517/ccdc.csd.cc2dq15c, https://dx.doi.org/10.5517/ccdc.csd.cc2dq16d, https://dx.doi.org/10.5517/ccdc.csd.cc2dq17f, https://dx.doi.org/10.5517/ccdc.csd.cc2dq18g, https://dx.doi.org/10.5517/ccdc.csd.cc2dq19h (show fewer)
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title = "Solid state structure and hydrogen bonding of some cyclic NH carboximides",

abstract = "Thirteen new crystal structures of cyclic NH carboximides have been determined and are compared with respect to the mode of intermolecular hydrogen bonding observed in the crystal. The structures include a new cyclobutane-fused succinimide, seven new simple bi- and tricyclic succinimides derived from Diels-Alder reactions of maleimide, three methylated glutarimides, a morpholinedione and adipimide, the first seven-membered ring NH carboximide to be structurally characterised. Overall seven of the compounds adopt a ribbon structure, five show centro-symmetric dimers, and one has bonding between NH and a remote bridging ether oxygen. Halogen bonding was also detected in one case.",

keywords = "Hydrogen bonding, Dimer, Ribbon, Succinimide, Glutarimide, Halogen bonding",

author = "Aitken, {R Alan} and Nelson, {Alexander J B} and Slawin, {Alexandra M .Z.} and Sonecha, {Dheirya K.}",

year = "2023",

month = jan,

day = "15",

doi = "10.3390/cryst13010150",

language = "English",

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journal = "Crystals",

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T1 - Solid state structure and hydrogen bonding of some cyclic NH carboximides

AU - Aitken, R Alan

AU - Nelson, Alexander J B

AU - Slawin, Alexandra M .Z.

AU - Sonecha, Dheirya K.

PY - 2023/1/15

Y1 - 2023/1/15

N2 - Thirteen new crystal structures of cyclic NH carboximides have been determined and are compared with respect to the mode of intermolecular hydrogen bonding observed in the crystal. The structures include a new cyclobutane-fused succinimide, seven new simple bi- and tricyclic succinimides derived from Diels-Alder reactions of maleimide, three methylated glutarimides, a morpholinedione and adipimide, the first seven-membered ring NH carboximide to be structurally characterised. Overall seven of the compounds adopt a ribbon structure, five show centro-symmetric dimers, and one has bonding between NH and a remote bridging ether oxygen. Halogen bonding was also detected in one case.

AB - Thirteen new crystal structures of cyclic NH carboximides have been determined and are compared with respect to the mode of intermolecular hydrogen bonding observed in the crystal. The structures include a new cyclobutane-fused succinimide, seven new simple bi- and tricyclic succinimides derived from Diels-Alder reactions of maleimide, three methylated glutarimides, a morpholinedione and adipimide, the first seven-membered ring NH carboximide to be structurally characterised. Overall seven of the compounds adopt a ribbon structure, five show centro-symmetric dimers, and one has bonding between NH and a remote bridging ether oxygen. Halogen bonding was also detected in one case.

KW - Hydrogen bonding

KW - Dimer

KW - Ribbon

KW - Succinimide

KW - Glutarimide

KW - Halogen bonding

U2 - 10.3390/cryst13010150

DO - 10.3390/cryst13010150

M3 - Article

SN - 2073-4352

VL - 13

JO - Crystals

JF - Crystals

IS - 1

M1 - 150

ER -

Solid state structure and hydrogen bonding of some cyclic NH carboximides

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CCDC 2225704-2225716: Experimental Crystal Structure Determination

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