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Crystal structures of 2-[3,5-bis-(bromo-meth-yl)-2,4,6-tri-ethyl-benz-yl]isoindoline-1,3-dione and 2-{5-(bromo-meth-yl)-3-[(1,3-dioxoisoindolin-2-yl)meth-yl]-2,4,6-tri-ethyl-benz-yl}isoindoline-1,3-dione.

ABSTRACT: The title compounds, C₂₃H₂₅Br₂NO₂ (1) and C₃₁H₂₉BrN₂O₄ (2), crystallize in the space group P2₁/n with two (1-A and 1-B) and one mol-ecules, respectively, in the asymmetric unit of the cell. The mol-ecular conformation of these compounds is stabilized by intra-molecular C-H⋯O hydrogen bonds and C-H⋯N or C-H⋯π inter-actions. 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 inter-molecular C-H⋯O hydrogen-bonding inter-actions.

SUBMITTER: Stapf M

PROVIDER: S-EPMC8423014 | biostudies-literature |

REPOSITORIES: biostudies-literature

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2-{2,4,6-Tris(bromo-meth-yl)-3,5-bis-[(1,3-dioxoisoindolin-2-yl)meth-yl]benz-yl}iso-indoline-1,3-dione toluene monosolvate.

Project description:In the title compound, C36H24Br3N3O6·C7H8, the toluene solvent mol-ecule is associated with the receptor mol-ecule via C-H?? bonding. The planes of the phthalimido groups are inclined at 77.0?(1), 63.0?(1) and 77.8?(1)° with respect to the benzene ring. The mol-ecular conformation is stabilized by C-H?O and C-H?Br hydrogen bonds. The crystal structure features non-classical hydrogen bonds of the C-H?N, C-H?O and C-H?Br type, leading to a three-dimensional cross-linking of molecules. The pattern of non-covalent inter-molecular bonding is completed by O?Br halogen bonds [3.306?(3)?Å], which link the receptor mol-ecules into infinite strands extending along the a-axis direction.

| S-EPMC3998546 | biostudies-literature

2-(3-Bromo-prop-yl)isoindoline-1,3-dione.

Project description:In the title compound, C(11)H(10)BrNO(2), the dihedral angle between the five- and six-membered rings of the phthalamide system is 1.00?(16)°. There are no significant inter-molecular inter-ations except for van der Waals contacts.

| S-EPMC2971232 | biostudies-literature

2-(2-Bromo-eth-yl)isoindoline-1,3-dione.

Project description:The asymmetric unit of the title compound, C(10)H(8)BrNO(2), contains three crystallographically independent mol-ecules. Two of the N-C-C-Br side chains adopt anti conformations [torsion angles = -179.8?(5) and -179.4?(4)°] and the other is gauche [-66.5?(6)°]. The crystal structure features short Br?O [3.162?(5)?Å] contacts, C-H?O hydrogen bonds and numerous ?-? stacking inter-actions [centroid-centroid separations = 3.517?(4)-3.950?(4)?Å].

| S-EPMC3247571 | biostudies-literature

2-(2-Fluoro-4-hy-droxy-benz-yl)isoindoline-1,3-dione.

Project description:In the title compound, C(15)H(10)FNO(3), the dihedral angle between the isoindoline-1,3-dione and 3-fluoro-4-methyl-phenol groups is 86.88 (8)°. The isoindoline-1,3-dione fragment is almost planar, with an r.m.s. deviation of 0.0154 Å within the group. Inter-molecular C-H⋯O hydrogen bonds generate C(6) chains running parallel to the [010] direction.

| S-EPMC3414933 | biostudies-literature

2-{[(4-Methoxy-phen-yl)dimethyl-silyl]meth-yl}isoindoline-1,3-dione.

Project description:In the course of our studies of silicon-containing anti-cancer compounds, the title compound, C(18)H(19)NO(3)Si, was synthesized. The mol-ecular geometry including bond distances and angles involving the Si atoms are typical. Torsion angles associated with the isoindoline ring and the silyl group [C-N-C(methyl-ene)-Si = 90.5?(2) and -93.1?(2)°] indicate that there is no inter-action between the O and Si atoms despite silicon's high affinity for oxygen.

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2-[4-tert-Butyl-5-(2-chloro-benz-yl)-1,3-thia-zol-2-yl]isoindoline-1,3-dione.

Project description:In the title compound, C(22)H(19)ClN(2)O(2)S, the dihedral angle between the phenyl-ene ring and the phthalimide ring system is 4.4?(1)°. There is no hydrogen bonding or ?-? stacking in the crystal structure.

| S-EPMC3009081 | biostudies-literature

2-[(1-Methyl-1H-pyrrol-2-yl)carbonyl-meth-yl]isoindoline-1,3-dione.

Project description:The asymmetric unit of the title compound, C(15)H(12)N(2)O(3), contains two almost identical mol-ecules forming an nearly C(2-)symmetric dimeric pattern. The dihedral angles between the pyrrole ring and the phthalimide unit are 82.95?(8) and 86.57?(8)° for the two mol-ecules. Within such a dimer, the phthalimide units of the two mol-ecules form a dihedral angle of 1.5?(5)°.

| S-EPMC2970463 | biostudies-literature

2-{(1R,2R)-2-[Bis(4-methyl-benz-yl)amino]-cyclo-hex-yl}isoindoline-1,3-dione.

Project description:In the title mol-ecule, C(30)H(32)N(2)O(2), the two tolyl rings form dihedral angles of 65.8?(1) and 6.6?(1)° with the isoindole-1,3-dione mean plane. The cyclo-hexane ring adopts a chair conformation.

| S-EPMC3120613 | biostudies-literature

2-Benzyl-5-meth-oxy-isoindoline-1,3-dione.

Project description:The title N-benzyl-phthalimide derivative, C16H13NO3, consists of two planar moieties, viz. the phthalimide system (r.m.s. deviation = 0.007?Å) and the phenyl ring, which make a dihedral angle of 84.7?(6)°. The meth-oxy group is almost coplanar with the phathalimide ring, as shown by the C-C-O-C torsion angle of -171.5?(2)°. In the crystal, the mol-ecules are self-assembled via non-classical C-H?O hydrogen bonds, forming a tape motif along [110].

| S-EPMC3790449 | biostudies-literature

2-[2-(Methyl-sulfon-yl)eth-yl]isoindoline-1,3-dione.

Project description:In the mol-ecule of the title compound, C(11)H(11)NO(4)S, the isoindoline ring system is almost planar with a maximum deviation of 0.008?(3)Å. In the crystal structure, inter-molecular C-H?O inter-actions link the mol-ecules into a three-dimensional network. ?-? contacts between the isoindoline rings [centroid-centroid distances = 3.592?(1) and 3.727?(1)?Å] may further stabilize the structure.

| S-EPMC2977474 | biostudies-literature

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