Crystal structure and Hirshfeld surface analysis of 4,5-dibromo-6-methyl-2-phenyl-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1<i>H</i>-isoindol-1-one

Mertsalov, Dmitriy F.; Nadirova, Maryana A.; Chervyakova, Lala V.; Grigoriev, Mikhail S.; Shelukho, Evgeniya R.; Çelikesir, Sevim Türktekin; Akkurt, Mehmet; Mlowe, Sixberth

doi:10.1107/s205698902100116x

Acta Cryst E

2021

DOI: 10.1107/s205698902100116x

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Crystal structure and Hirshfeld surface analysis of 4,5-dibromo-6-methyl-2-phenyl-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1H-isoindol-1-one

Dmitriy F. Mertsalov¹,

Maryana A. Nadirova²,

Lala V. Chervyakova³

et al.

Abstract: In the title compound, C15H15Br2NO2, two bridged tetrahydrofuran rings adopt envelope conformations with the O atom as the flap. The pyrrolidine ring also adopts an envelope conformation with the spiro C atom as the flap. In the crystal, the molecules are linked into dimers by pairs of C—H...O hydrogen bonds, thus generating R 2 2(18) rings. The crystal packing is dominated by H...H, Br...H, H...π and Br...π interactions. One of the Br atoms is disordered over two sites with… Show more

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Cited by 3 publications

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(3aS,4R,5R,6S,7aR)-4,5-Dibromo-2-[4-(trifluoromethyl)phenyl]-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1H-isoindol-1-one: crystal structure and Hirshfeld surface analysis

et al. 2021

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The asymmetric unit of the title compound, C15H12Br2F3NO2, consists of two crystallographically independent molecules. In both molecules, the pyrrolidine and tetrahydrofuran rings adopt an envelope conformation. In the crystal, molecule pairs generate centrosymmetric rings with R 2 2(8) motifs linked by C—H...O hydrogen bonds. These pairs of molecules form a tetrameric supramolecular motif, leading to molecular layers parallel to the (100) plane by C—H...π and C—Br...π interactions. Interlayer van der Waals and interhalogen interactions stabilize molecular packing. The F atoms of the CF3 groups of both molecules are disordered over two sets of sites with refined site occupancies of 0.60 (3)/0.40 (3) and 0.640 (15)/0.360 (15). The most important contributions to the surface contacts of both molecules are from H...H (23.8 and 22.4%), Br...H/H...Br (18.3 and 12.3%), O...H/H...O (14.3 and 9.7%) and F...H/H...F (10.4 and 19.1%) interactions, as concluded from a Hirshfeld surface analysis.

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(3aS,4R,5R,6S,7aR)-4,5-Dibromo-2-[4-(trifluoromethyl)phenyl]-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1H-isoindol-1-one: crystal structure and Hirshfeld surface analysis

et al. 2021

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Structural, Hirshfeld surface and three-dimensional interaction-energy studies of 1,3,5-triethyl 2-amino-3,5-dicyano-4,6-bis(4-fluorophenyl)cyclohex-1-ene-1,3,5-tricarboxylate

Chandana¹,

Ganesha²,

Sreenatha³

et al. 2023

Acta Cryst E

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In the title compound, C29H27F2N3O6, which crystallizes in the monoclinic space group P21/c, the cyclohexenone ring is puckered and adopts an envelope conformation. The crystal structure features various intermolecular interactions, such as N—H...O, C—H...N and C—H...O. These interactions were investigated using Hirshfeld surface analysis and the three-dimensional interaction energies were calculated using the B3LYP/6–31 G(d,p) energy density model.

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Crystal structures and Hirshfeld surface analyses of N,N-dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol tribromide (1/1), N,N-dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol dibromidoiodate (1/1) and N,N-dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol dichloridoiodate (1/1)

Mammadova,

Mertsalov,

Shchevnikov

et al. 2023

Acta Crystallogr E Cryst Commun

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In the title compounds, N,N-dimethylacetamide–1-(dimethyl-λ4-azanylidene)ethan-1-ol tribromide (1/1), C4H9NO·C4H10NO+·Br3 − or [(C4H9NO)·(C4H10NO)](Br3), (I), N,N-dimethylacetamide–1-(dimethyl-λ4-azanylidene)ethan-1-ol dibromidoiodate (1/1), C4H9NO·C4H10NO+·Br2I− or [(C4H9NO)·(C4H10NO)](Br2I), (II), and N,N-dimethylacetamide–1-(dimethyl-λ4-azanylidene)ethan-1-ol dichloridoiodate (1/1), C4H9NO·C4H10NO+·Cl2I− or [(C4H9NO)·(C4H10NO)]·(Cl2I), (III), all the anions are almost linear in geometry and all the cations, except for the methyl H atoms, are essentially planar. In the crystal structure of (I), the cations are linked by pairs of C—H...O hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif. These dimers also exhibit O—H...O hydrogen bonding. Dimerized cation pairs and anions are arranged in columns along the a axis. In the crystal of (II), the cations are linked by pairs of O—H...O and C—H...O hydrogen bonds, forming an R 4 4(14) ring motif. These groups of cations and the anions form individual columns along the a axis and jointly reside in planes roughly parallel to (011). In the crystal of (III), cations and anions also form columns parallel to the a axis, resulting in layers parallel to the (020) plane. Furthermore, the crystal structures of (I), (II) and (III) are consolidated by strong halogen (Br and/or I and/or Cl)...H and weak van der Waals interactions. In addition to the structural evaluation, a Hirshfeld surface analysis was carried out.

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Crystal structure and Hirshfeld surface analysis of 4,5-dibromo-6-methyl-2-phenyl-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1H-isoindol-1-one

Cited by 3 publications

References 42 publications

(3aS,4R,5R,6S,7aR)-4,5-Dibromo-2-[4-(trifluoromethyl)phenyl]-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1H-isoindol-1-one: crystal structure and Hirshfeld surface analysis

(3aS,4R,5R,6S,7aR)-4,5-Dibromo-2-[4-(trifluoromethyl)phenyl]-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1H-isoindol-1-one: crystal structure and Hirshfeld surface analysis

Structural, Hirshfeld surface and three-dimensional interaction-energy studies of 1,3,5-triethyl 2-amino-3,5-dicyano-4,6-bis(4-fluorophenyl)cyclohex-1-ene-1,3,5-tricarboxylate

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