2-{2,4,6-Tris(bromomethyl)-3,5-bis[(1,3-dioxoisoindolin-2-yl)methyl]benzyl}isoindoline-1,3-dione toluene monosolvate

Koch, Niklas; Seichter, Wilhelm; Mazik, Monika

doi:10.1107/s1600536814004383

Cited by 5 publications

(2 citation statements)

References 11 publications

(10 reference statements)

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“…Regarding the description of crystal structures of tri-to hexasubstituted benzene derivatives, the number of hits could be reduced to three relevant entries. This includes two hexasubstituted benzene derivatives consisting of three isoindoline-1,3-dione groups (phthalimidomethyl groups) and either methoxy (IDOBIO; Rosien et al, 2013) or bromomethyl groups (LOFBIT; Koch et al, 2014) in each of the 2-, 4-and 6-positions of the benzene ring. Furthermore, a 1,3,5-trisubstituted benzene derivative, namely 3,5-bis(phthalimidomethyl)phenyl-tert-butyldimethylsilyl ether (WIKRAK; Domínguez et al, 2007), has been found.…”

Section: Database Surveymentioning

confidence: 99%

Crystal structures of 2-[3,5-bis(bromomethyl)-2,4,6-triethylbenzyl]isoindoline-1,3-dione and 2-{5-(bromomethyl)-3-[(1,3-dioxoisoindolin-2-yl)methyl]-2,4,6-triethylbenzyl}isoindoline-1,3-dione

Stapf¹,

Leibiger²,

Schwarzer³

et al. 2021

Acta Cryst E

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The title compounds, C23H25Br2NO2 (1) and C31H29BrN2O4 (2), crystallize in the space group P21/n with two (1-A and 1-B) and one molecules, respectively, in the asymmetric unit of the cell. The molecular conformation of these compounds is stabilized by intramolecular C—H...O hydrogen bonds and C—H...N or C—H...π interactions. The crystal structure of 1 features a relatively strong Br...O=C halogen bond, which is not observed in the case of 2. Both crystal structures are characterized by the presence of C—H...Br hydrogen bonds and numerous intermolecular C—H...O hydrogen-bonding interactions.

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Section: Database Surveymentioning

confidence: 99%

Crystal structures of 2-[3,5-bis(bromomethyl)-2,4,6-triethylbenzyl]isoindoline-1,3-dione and 2-{5-(bromomethyl)-3-[(1,3-dioxoisoindolin-2-yl)methyl]-2,4,6-triethylbenzyl}isoindoline-1,3-dione

Stapf¹,

Leibiger²,

Schwarzer³

et al. 2021

Acta Cryst E

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“…Moreover, the Br1Á Á ÁCg(B) distance of 3.317 (2) Å and the well-defined bonding geometry [C9-Br1Á Á ÁCg(B) = 173.0 (1) ] indicate the presence of an intermolecular BrÁ Á Á halogen bond (Mazik et al, 2010a,b;Koch et al, 2017;Legon, 1999;Megrangolo & Resnati, 2008). The distance of 3.213 (2) Å between atom Br2 and amide atom O1A of an adjacent molecule [symmetry code: (A) x + 1, y À 1, z], which is considerably less than the sum of the van der Waals radii of the respective atoms (3.37 Å ), suggests the existence of an attractive BrÁ Á ÁO halogen bond (Politzer et al, 2007;Koch et al, 2014Koch et al, , 2015. One of the host molecules participates in offsetstacking [CgÁ Á ÁCg = 3.709 (2) Å ; symmetry code: Àx, Ày, Àz + 1].…”

Section: Figurementioning

confidence: 99%

Crystal structures of the dioxane hemisolvates ofN-(7-bromomethyl-1,8-naphthyridin-2-yl)acetamide and bis[N-(7-dibromomethyl-1,8-naphthyridin-2-yl)acetamide]

2017

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Supporting information: this article has supporting information at journals.iucr.org/eCrystal structures of the dioxane hemisolvates of N-(7-bromomethyl-1,8-naphthyridin-2-yl)acetamide and bis [N-(7-dibromomethyl-1,8-naphthyridin-2-yl) The syntheses and crystal structures of N-(7-bromomethyl-1,8-naphthyridin-2-yl)acetamide dioxane hemisolvate, C 11 H 10 BrN 3 OÁ0.5C 4 H 8 O 2 , (I), and bis[N-(7-dibromomethyl-1,8-naphthyridin-2-yl)acetamide] dioxane hemisolvate, 2C 11 H 9 Br 2 N 3 OÁ0.5C 4 H 8 O 2 , (II), are described. The molecules adopt a conformation with the N-H hydrogen pointing towards the lone electron pair of the adjacent naphthyridine N atom. The crystals of (I) are stabilized by a three-dimensional supramolecular network comprising N-HÁ Á ÁN, C-HÁ Á ÁN and C-HÁ Á ÁO hydrogen bonds, as well as C-BrÁ Á Á halogen bonds. The crystals of compound (II) are stabilized by a three-dimensional supramolecular network comprising N-HÁ Á ÁN, C-HÁ Á ÁN and C-HÁ Á ÁO hydrogen bonds, as well as C-HÁ Á Á contacts and C-BrÁ Á Á halogen bonds. The structure of the substituent attached in the 7-position of the naphthyridine skeleton has a fundamental influence on the pattern of intermolecular noncovalent bonding. While the Br atom of (I) participates in weak C-BrÁ Á ÁO guest and C-BrÁ Á Á contacts, the Br atoms of compound (II) are involved in host-host interactions via C-BrÁ Á ÁO C, C-BrÁ Á ÁN and C-BrÁ Á Á bonding. Chemical contextIn recent decades, 1,8-naphthyridines have attracted increasing interest because of their biological and medicinal activities (Ferrarini et al., 1998;Roma et al., 2010;Badaweh et al., 2001;Litvinov, 2004), as ligands in the synthesis of metal complexes (Tang et al., 2015;Matveeva et al., 2013;Kolotuchin & Zimmerman, 1998) and as building blocks for various supramolecular systems (Kolotuchin & Zimmerman, 1998;Park et al., 2005;Liang et al., 2012). Compound (I) represents a useful precursor for the synthesis of artificial receptor molecules, for example, for carbohydrate receptors bearing naphthyridine units (Mazik & Cavga, 2007;Mazik & Sicking, 2001;Cuntze et al., 1995). Structural commentaryThe molecular structures of the title compounds, (I) and (II), are illustrated in Figs. 1 and 2, respectively. The asymmetric unit of compound (I) consists of one molecule of the naphthyridine derivative and one half of a 1,4-dioxane solvent molecule, with the whole molecule being generated by inversion symmetry. The naphthyridine ring of the host molecule is essentially planar [maximum deviations from the mean plane being 0.034 (3) Å for N1 and À0.034 (3) Å for C6]. The plane defined by the acetamido group is inclined at an angle of 18.9 (2) with respect to the mean plane of the 1,8-naphthyr- idine moiety. The torsion angle along the atomic sequence N2-C1-C9-Br1 is 83.6 (4) . The dioxane molecule is connected to the host molecule via C-HÁ Á ÁO hydrogen bonding (Table 1 and Fig. 1).The asymmetric unit of the inclusion compound (II) contains two crystallographically independent, but conformationally similar ...

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Crystalline Ammonium Complexes of Trimethyl‐ and Triethylbenzene‐Based Tripodal Compounds Bearing Pyrazole and Indazole Groups

et al. 2018

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Crystalline complexes of NH4+PF6– with trimethyl‐ and triethylbenzene‐based tripodal compounds, bearing either pyrazole or indazole groups, were prepared and characterized by X‐ray diffraction studies. The supramolecular motifs observed in the crystal structures and the conformations of the tripodal molecules have been the subject of a detailed analysis and are described in this paper. The pyrazole‐bearing side arms of the hosts with a trimethylbenzene scaffold are arranged in an aaa fashion and form a cavity including the ammonium ion. In the case of the triethylbenzene derivatives, the fully alternating arrangement of the pyrazole/indazole and ethyl groups is observed and by taking the ethyl groups into account, the conformation can be defined as ab′ab′ab′. The conformations observed in the crystals of the free host molecules can be defined as ab′ab′ba′ with the indazole‐bearing arms arranged in an aab fashion. The crystal packings of the complexes are, among other things, characterized by the presence of NH···F and CH···F hydrogen bonds as well as by CBr···N and CBr···π halogen bonds in the case of the bromo‐substituted derivatives.

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2-{2,4,6-Tris(bromomethyl)-3,5-bis[(1,3-dioxoisoindolin-2-yl)methyl]benzyl}isoindoline-1,3-dione toluene monosolvate

Cited by 5 publications

References 11 publications

Crystal structures of 2-[3,5-bis(bromomethyl)-2,4,6-triethylbenzyl]isoindoline-1,3-dione and 2-{5-(bromomethyl)-3-[(1,3-dioxoisoindolin-2-yl)methyl]-2,4,6-triethylbenzyl}isoindoline-1,3-dione

Crystal structures of 2-[3,5-bis(bromomethyl)-2,4,6-triethylbenzyl]isoindoline-1,3-dione and 2-{5-(bromomethyl)-3-[(1,3-dioxoisoindolin-2-yl)methyl]-2,4,6-triethylbenzyl}isoindoline-1,3-dione

Crystal structures of the dioxane hemisolvates ofN-(7-bromomethyl-1,8-naphthyridin-2-yl)acetamide and bis[N-(7-dibromomethyl-1,8-naphthyridin-2-yl)acetamide]

Crystalline Ammonium Complexes of Trimethyl‐ and Triethylbenzene‐Based Tripodal Compounds Bearing Pyrazole and Indazole Groups

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