Intermolecular interactions in two (ferrocenylmethyl)benzimidazoles incorporating the 4-MeOC6H4and 3,4-(MeO)2C6H3groups: analysis of MeO—C—C distortions from ideal 120° geometry

Gallagher, John F.; Hanlon, Keith; Howarth, Joshua

doi:10.1107/s0108270101015591

Cited by 11 publications

(5 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The C-N distances, N-C-N and C-N-C angles of the title compounds are similar and comparable to the data reported for the related compounds [12][13][14][15][16][17]. Distortions from the ideal 120 o angle about the MeO-C-C groups in (2) are evident, with the average angles of 115.1(1) and 125.1 (1) o , which are consistent with the other benzimidazoles with the MeO group [18]. Packing diagrams of (1) and (2) are shown in figures 3 and 4, respectively.…”

Section: Methodssupporting

confidence: 87%

Synthesis, crystal and molecular structures of 1-n-butyl-2-(3′-chlorophenyl)-1H-benzimidazole-5-carbonitrile hemihydrate and 1-n-butyl-2-(3′,4′-dimethoxyphenyl)-1H-benzimidazole-5-carbonitrile

Kazak

Yılmaz

Göker

et al. 2006

Cryst. Res. Technol.

View full text Add to dashboard Cite

Section: Methodssupporting

confidence: 87%

Synthesis, crystal and molecular structures of 1-n-butyl-2-(3′-chlorophenyl)-1H-benzimidazole-5-carbonitrile hemihydrate and 1-n-butyl-2-(3′,4′-dimethoxyphenyl)-1H-benzimidazole-5-carbonitrile

Kazak

Yılmaz

Göker

et al. 2006

Cryst. Res. Technol.

View full text Add to dashboard Cite

“…The syn-torsion data is close to the average isophthaloyl (O C)C 6 H 4 (C=O) torsion angle noted previously (Evans & Gale, 2004;Mocilac & Gallagher, 2013, 2014Gallagher & Mocilac, 2021). In the four dimethoxypyrimidine rings, the methoxy groups all adopt similar conformations, as noted previously (Gallagher et al, 2001). The proximally related pyridine rings are almost orthogonal to one another at 87.00 (10), 87.09 (10) � and with the opposite (distal-related) pyridine rings almost parallel at 9.25 (11), 0.97 (11) � .…”

Section: Structural Commentarysupporting

confidence: 73%

The unusual (syn-/anti-)₂ conformation of a dimethoxypyrimidyl-based tennimide

Mocilac,

Pohl,

Gallagher

2023

Acta Cryst E

Self Cite

View full text Add to dashboard Cite

The tennimide macrocycle, (I) (C52H40N16O16.0.167H2O), was synthesized from 2-amino-4,6-dimethoxypyrimidine and pyridine-2,6-dicarbonyl dichloride. Compound (I) represents the first tennimide incorporating pyridine rings in the macrocycle scaffold. In the macrocycle ring, the carbonyl groups at each successive dicarbonyl(pyridine) moiety adopt the (syn/anti)2 conformation. This contrasts with all previously reported tetraimide macrocycles, which exhibit the (syn)4 conformation. The effect is to close any potential cavity or niche by having two of the central pyridine C5N rings aligned close to each other [with closest pyridine Cg...Cg ring centroid separations of 3.5775 (19) Å; closest C...C = 3.467 (5) Å]. A partial occupancy water molecule (with s.o.f. = 0.167), resides with its oxygen atom on a twofold axis at hydrogen-bonding distances to the carbonyl O atom, in a molecular niche between two pyridine rings. Macrocyles of (I) have all six C=O groups and all eight methoxy O atoms present on the macrocycle surface. However, all twelve N atoms are effectively shielded on steric grounds from any potential intermolecular interactions. The remaining two C=O O atoms interact with the partial occupancy water molecule via two O—H...O=C hydrogen bonds. Macrocycles of (I) stack as one-dimensional chains along the b-axis direction with primary intermolecular interactions involving weak C—H...O=C/OCH3/H2O contacts. Chains interlock weakly via methoxy–methoxy C—H...O interactions into two-dimensional sheets.

show abstract

“…The MeO group at atom C14 displays an OÐCÐC distortion, with O3Ð C14ÐC13/C15 angles of 115.60 (13) and 123.34 (13) (transoid to atom C13 and the C 5 chain). These distortions, especially that of the C Me ÐOÐCÐC torsion-angle orientation with respect to the OÐCÐC angle, have been commented on previously (Bruno et al, 2001;Gallagher et al, 2001;Wiedenfeld et al, 2003).…”

mentioning

confidence: 99%

tert-Butyl 5-methoxy-3-pentylindole-1-carboxylate

2004

Self Cite

View full text Add to dashboard Cite

The molecule of the title compound, C 19 H 27 NO 3 , is essentially planar, with all non-H atoms within 0.2 A Ê of the ninemembered indole plane, except for the three tert-butyl C atoms. The C 5 pentyl chain is in an extended conformation, with three torsion angles of 179.95 (13), 179.65 (13) and À178.95 (15) (the latter two angles include the C atoms of the C 5 chain only). Three intramolecular CÐHÁ Á ÁO C contacts are present (CÁ Á ÁO < 3.05 A Ê and CÐHÁ Á ÁO > 115 ), and an intermolecular CÐHÁ Á ÁO C contact and %±% stacking complete the intermolecular interactions. CommentThe key biochemical roles played by the indole ring in nature ensure that this heterocyclic system continues to attract scrutiny from medicinal and synthetic chemists. It is a common motif for drug targets and, as such, the development of new diversity-tolerant routes to this privileged biological scaffold continues to be of signi®cant bene®t (Gribble, 1996) and forms the basis of a wide variety of drugs, including the antiin¯ammatory agent Indomethacin, Reserpine (exploited as a hypotensive agent) and Sumatriptan (used for the treatment of migraine). Historically, interest in indoles arose from the isolation and characterization of indole alkaloids, which, along with their semi-synthetic derivatives, have potent central nervous system activity. Many recent advances in indole synthesis have focused on metal-mediated procedures, with copper, palladium, tin, titanium and zirconium being the most prevalent (Sundberg, 1996;Gribble, 2000).Recently, we reported a new approach to the synthesis of the indole scaffold, exploiting a controlled organolithium addition to functionalized styrenes, with the CÐC bond formation reaction as the key synthetic step. A signi®cant bene®t of this strategy is that it can provide a direct route for the introduction of further structural diversity onto the ring system (Coleman & O'Shea, 2003), which may be of bene®t for combinatorial library generations. Despite the prevalence of indole structures in the Cambridge Structural Database (CSD; Allen, 2002), there are no structures that contain the indole skeleton and atoms substituted at the 1-(C), 3-(C) and 5-positions (O) for direct comparison with the title compound, (I). However, many derivatives that contain the tryptophan residue are present in the CSD.Pertinent bond lengths and angles for (I) are listed in Table 1 and the molecular structure is depicted in Fig. 1. The bond lengths and angles are as expected for indole systems (Fig. 1). Localization in the aromatic rings is discernible in (I), with a C1AÐC2A bond length of 1.3481 (19) A Ê [the other NC 4 -ring CÐC lengths are 1.4496 (19) and 1.4090 (18) A Ê ], and CÐN distances of 1.4022 (16) and 1.4076 (18) A Ê ; in the C 6 ring, the C13ÐC14 and C15ÐC16 bond lengths are 1.379 (2) and 1.386 (2) A Ê , respectively. In the C 5 pentyl chain, the CÐC bond lengths for atoms C1±C5 are in the narrow range 1.509 (2)±1.5195 (19) A Ê ; the C2AÐC1ÐC2 angle opens to 114.98 (12) , and the remaining CÐCÐC angles along the c...

show abstract

Intermolecular interactions in two (ferrocenylmethyl)benzimidazoles incorporating the 4-MeOC₆H₄and 3,4-(MeO)₂C₆H₃groups: analysis of MeO—C—C distortions from ideal 120° geometry

Cited by 11 publications

References 24 publications

Synthesis, crystal and molecular structures of 1-n-butyl-2-(3′-chlorophenyl)-1H-benzimidazole-5-carbonitrile hemihydrate and 1-n-butyl-2-(3′,4′-dimethoxyphenyl)-1H-benzimidazole-5-carbonitrile

Synthesis, crystal and molecular structures of 1-n-butyl-2-(3′-chlorophenyl)-1H-benzimidazole-5-carbonitrile hemihydrate and 1-n-butyl-2-(3′,4′-dimethoxyphenyl)-1H-benzimidazole-5-carbonitrile

The unusual (syn-/anti-)₂ conformation of a dimethoxypyrimidyl-based tennimide

tert-Butyl 5-methoxy-3-pentylindole-1-carboxylate

Contact Info

Product

Resources

About

Intermolecular interactions in two (ferrocenylmethyl)benzimidazoles incorporating the 4-MeOC6H4and 3,4-(MeO)2C6H3groups: analysis of MeO—C—C distortions from ideal 120° geometry

Cited by 11 publications

References 24 publications

Synthesis, crystal and molecular structures of 1-n-butyl-2-(3′-chlorophenyl)-1H-benzimidazole-5-carbonitrile hemihydrate and 1-n-butyl-2-(3′,4′-dimethoxyphenyl)-1H-benzimidazole-5-carbonitrile

Synthesis, crystal and molecular structures of 1-n-butyl-2-(3′-chlorophenyl)-1H-benzimidazole-5-carbonitrile hemihydrate and 1-n-butyl-2-(3′,4′-dimethoxyphenyl)-1H-benzimidazole-5-carbonitrile

The unusual (syn-/anti-)2 conformation of a dimethoxypyrimidyl-based tennimide

tert-Butyl 5-methoxy-3-pentylindole-1-carboxylate

Contact Info

Product

Resources

About

Intermolecular interactions in two (ferrocenylmethyl)benzimidazoles incorporating the 4-MeOC₆H₄and 3,4-(MeO)₂C₆H₃groups: analysis of MeO—C—C distortions from ideal 120° geometry

The unusual (syn-/anti-)₂ conformation of a dimethoxypyrimidyl-based tennimide