3-Cyano-1-[4-(1,3-dithian-2-yl)butyl]-1,4,5,6-tetrahydropyridine

Hussain, Zafar I.; Fleming, Fraser F.; Norman, Richard E.; Chang, S. C.

doi:10.1107/s010827019501345x

Cited by 4 publications

(5 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The bond lengths and angles of the phenyl rings of (I)-(III) are consistent with those observed in similar structures (Patel et al, 2002a,b,c;Black et al, 1992;Hussain et al, 1996). The deviations of the nitrile atoms (C12 and N2) from the mean plane of the pyridine ring system (N1/C1/C8-C11) are À0.0422 (1) and À0.0896 (5) Å , respectively, in (I), À0.0081 (5) and À0.0416 (2) Å , respectively, in (II), and À0.0624 (4) and À0.1038 (1) Å , respectively, in (III), indicative of coplanarity.…”

Section: Resultssupporting

confidence: 89%

C—H...O and C—H...N interactions in three hexahydrocycloocta[b]pyridine-3-carbonitriles

Vishnupriya¹,

Suresh²,

Maharani

et al. 2014

Acta Crystallogr C

View full text Add to dashboard Cite

The structures of three new pyridine derivatives, 2-methoxy-4-(4-methoxyphenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carbonitrile, C20H22N2O2, (I), 2-ethoxy-4-(3-nitrophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carbonitrile, C20H21N3O3, (II), and 2-ethoxy-4-(4-methoxyphenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carbonitrile, C21H24N2O2, (III), differ in the nature of the substituents either at the 2-position of the central pyridine ring or on the pendent aryl ring. This simple change in the structure substantially alters the intermolecular interaction patterns. The substituted phenyl group adopts a synclinal geometry with respect to the plane of the pyridine ring in all three compounds. In (I), a C-H···N interaction results in a one-dimensional chain parallel to the b axis. In (II), there are two C-H···N(nitrile) interactions from different symmetry-related molecules, resulting in a two-dimensional network parallel to the bc plane. There is also a weak C-H···O interaction from the ethoxy group to an adjacent nitro O atom. The present work is an example of how the simple replacement of a substituent in the main molecular scaffold may transform the structure type, paving the way for a variety of supramolecular motifs and consequently altering the complexity of the intermolecular interaction patterns.

show abstract

Section: Resultssupporting

confidence: 89%

C—H...O and C—H...N interactions in three hexahydrocycloocta[b]pyridine-3-carbonitriles

Vishnupriya¹,

Suresh²,

Maharani

et al. 2014

Acta Crystallogr C

View full text Add to dashboard Cite

show abstract

“…The ringpuckering parameters of the central THP ring are summarized as follows, with the values of dimethyl and dibenzyl derivatives, respectively, given inside the brackets. The cyano moiety, as observed in other structures, [3][4][5][6] remains linear with respect to the THP plane. The para-substituted phenyl ring stands vertical with the best THP plane (89.86(6)˚), which is also observed in the dibenzyl derivative (89.57(5)˚).…”

supporting

confidence: 77%

Crystal and Molecular Structure of 1,3-Diethyl-2-oxo-4,6-diphenyl-1,2,3,4-tetrahydropyridine-3-carbonitrile

Patel

Jotani²,

Shah

2006

Anal. Sci. X

View full text Add to dashboard Cite

“…Tetrahydropyridine ring of CSD refcode ZUHSIE (magenta) superimposed on Loracarbef (green) using the heavy atoms of the ring. In this instance three of the ring atoms (green spheres) have the same substitution pattern.…”

Section: Resultsmentioning

confidence: 99%

Validating and Understanding Ring Conformations Using Small Molecule Crystallographic Data

Cottrell

Olsson

Taylor

et al. 2012

J. Chem. Inf. Model.

View full text Add to dashboard Cite

Understanding the conformational preferences of ring structures is fundamental to structure-based drug design. Although the Cambridge Structural Database (CSD) provides information on the preferred conformations of small molecules, analyzing this data can be very time-consuming. In order to overcome this hurdle, tools have been developed for quickly extracting geometrical preferences from the CSD. Here we describe how the program Mogul has been extended to analyze and compare ring conformations, using a library derived from over 900 000 ring fragments in the CSD. We illustrate how these can be used to understand the conformational preferences of molecules in a crystal lattice and bound to proteins.

show abstract

3-Cyano-1-[4-(1,3-dithian-2-yl)butyl]-1,4,5,6-tetrahydropyridine

Cited by 4 publications

References 0 publications

C—H...O and C—H...N interactions in three hexahydrocycloocta[b]pyridine-3-carbonitriles

C—H...O and C—H...N interactions in three hexahydrocycloocta[b]pyridine-3-carbonitriles

Crystal and Molecular Structure of 1,3-Diethyl-2-oxo-4,6-diphenyl-1,2,3,4-tetrahydropyridine-3-carbonitrile

Validating and Understanding Ring Conformations Using Small Molecule Crystallographic Data

Contact Info

Product

Resources

About