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Crystal structures of 2-meth-oxy-isoindoline-1,3-dione, 1,3-dioxoisoindolin-2-yl methyl carbonate and 1,3-dioxo-2,3-di-hydro-1H-benzo[de]isoquinolin-2-yl methyl carbonate: three anti-convulsant compounds.

Ezemobi F, North H, Scott KR, Wutoh AK, Butcher RJ - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: There are also C-H⋯O hydrogen bonds and π-π inter-actions [inter-centroid distance = 3.407 (3) Å] present, forming slabs lying parallel to (001).In the crystal of (2), the A and B mol-ecules are linked by C-H⋯O hydrogen bonds, forming slabs parallel to (10-1), which are in turn linked via a number of π-π inter-actions [the most significant centroid-centroid distances are 3.4202 (7) and 3.5445 (7) Å], forming a three-dimensional structure.In the crystal of (3), the A and B mol-ecules are linked via C-H⋯O hydrogen bonds, forming a three-dimensional structure, which is consolidated by π-π inter-actions [the most significant inter-centroid distances are 3.575 (3) and 3.578 (3) Å].

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Affiliation: Department of Biology, College of Arts & Sciences, Howard University, 415 College Street NW, Washington, DC 20059, USA.

ABSTRACT
The title compounds, C9H7NO3, (1), C10H7NO5, (2), and C14H9NO5, (3), are three potentially anti-convulsant compounds. Compounds (1) and (2) are isoindoline derivatives and (3) is an iso-quinoline derivative. Compounds (2) and (3) crystallize with two independent mol-ecules (A and B) in their asymmetric units. In all three cases, the isoindoline and benzoiso-quinoline moieties are planar [r.m.s. deviations are 0.021 Å for (1), 0.04 and 0.018 Å for (2), and 0.033 and 0.041 Å for (3)]. The substituents attached to the N atom are almost perpendicular to the mean planes of the heterocycles, with dihedral angles of 89.7 (3)° for the N-O-Cmeth-yl group in (1), 71.01 (4) and 80.00 (4)° for the N-O-C(=O)O-Cmeth-yl groups in (2), and 75.62 (14) and 74.13 (4)° for the same groups in (3). In the crystal of (1), there are unusual inter-molecular C=O⋯C contacts of 2.794 (1) and 2.873 (1) Å present in mol-ecules A and B, respectively. There are also C-H⋯O hydrogen bonds and π-π inter-actions [inter-centroid distance = 3.407 (3) Å] present, forming slabs lying parallel to (001). In the crystal of (2), the A and B mol-ecules are linked by C-H⋯O hydrogen bonds, forming slabs parallel to (10-1), which are in turn linked via a number of π-π inter-actions [the most significant centroid-centroid distances are 3.4202 (7) and 3.5445 (7) Å], forming a three-dimensional structure. In the crystal of (3), the A and B mol-ecules are linked via C-H⋯O hydrogen bonds, forming a three-dimensional structure, which is consolidated by π-π inter-actions [the most significant inter-centroid distances are 3.575 (3) and 3.578 (3) Å].

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For mol­ecule A in compound (2), perpendicular inter­actions between atoms O1A and C9A (shown as dashed lines) link the mol­ecules into inversion dimers [symmetry code: (A) − x + 1, − y + 2, −z].
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fig6: For mol­ecule A in compound (2), perpendicular inter­actions between atoms O1A and C9A (shown as dashed lines) link the mol­ecules into inversion dimers [symmetry code: (A) − x + 1, − y + 2, −z].

Mentions: In the crystal of (3), the A and B mol­ecules are linked by C—H⋯O hydrogen bonds (Fig. 6 ▶ and Table 3 ▶), forming a three-dimensional structure, which is consolidated by π–π inter­actions [Cg1⋯Cg3iii = 3.578 (3), Cg2⋯Cg3iii = 3.575 (3) Å and Cg9⋯Cg10iv; Cg1, Cg2, Cg3, Cg9 and Cg10 are the centroids of rings N1A/C1A–C5A, C2A/C3A/C6A–C9A, C3A/C4A/C9A–C12A, C2B/C3B/C6B–C9B and C3B/C4B/C9B–C12B, respectively; symmetry codes: (iii) x, −y + , z − ; (iv) x, −y + , z + ].


Crystal structures of 2-meth-oxy-isoindoline-1,3-dione, 1,3-dioxoisoindolin-2-yl methyl carbonate and 1,3-dioxo-2,3-di-hydro-1H-benzo[de]isoquinolin-2-yl methyl carbonate: three anti-convulsant compounds.

Ezemobi F, North H, Scott KR, Wutoh AK, Butcher RJ - Acta Crystallogr Sect E Struct Rep Online (2014)

For mol­ecule A in compound (2), perpendicular inter­actions between atoms O1A and C9A (shown as dashed lines) link the mol­ecules into inversion dimers [symmetry code: (A) − x + 1, − y + 2, −z].
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257384&req=5

fig6: For mol­ecule A in compound (2), perpendicular inter­actions between atoms O1A and C9A (shown as dashed lines) link the mol­ecules into inversion dimers [symmetry code: (A) − x + 1, − y + 2, −z].
Mentions: In the crystal of (3), the A and B mol­ecules are linked by C—H⋯O hydrogen bonds (Fig. 6 ▶ and Table 3 ▶), forming a three-dimensional structure, which is consolidated by π–π inter­actions [Cg1⋯Cg3iii = 3.578 (3), Cg2⋯Cg3iii = 3.575 (3) Å and Cg9⋯Cg10iv; Cg1, Cg2, Cg3, Cg9 and Cg10 are the centroids of rings N1A/C1A–C5A, C2A/C3A/C6A–C9A, C3A/C4A/C9A–C12A, C2B/C3B/C6B–C9B and C3B/C4B/C9B–C12B, respectively; symmetry codes: (iii) x, −y + , z − ; (iv) x, −y + , z + ].

Bottom Line: There are also C-H⋯O hydrogen bonds and π-π inter-actions [inter-centroid distance = 3.407 (3) Å] present, forming slabs lying parallel to (001).In the crystal of (2), the A and B mol-ecules are linked by C-H⋯O hydrogen bonds, forming slabs parallel to (10-1), which are in turn linked via a number of π-π inter-actions [the most significant centroid-centroid distances are 3.4202 (7) and 3.5445 (7) Å], forming a three-dimensional structure.In the crystal of (3), the A and B mol-ecules are linked via C-H⋯O hydrogen bonds, forming a three-dimensional structure, which is consolidated by π-π inter-actions [the most significant inter-centroid distances are 3.575 (3) and 3.578 (3) Å].

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Biology, College of Arts & Sciences, Howard University, 415 College Street NW, Washington, DC 20059, USA.

ABSTRACT
The title compounds, C9H7NO3, (1), C10H7NO5, (2), and C14H9NO5, (3), are three potentially anti-convulsant compounds. Compounds (1) and (2) are isoindoline derivatives and (3) is an iso-quinoline derivative. Compounds (2) and (3) crystallize with two independent mol-ecules (A and B) in their asymmetric units. In all three cases, the isoindoline and benzoiso-quinoline moieties are planar [r.m.s. deviations are 0.021 Å for (1), 0.04 and 0.018 Å for (2), and 0.033 and 0.041 Å for (3)]. The substituents attached to the N atom are almost perpendicular to the mean planes of the heterocycles, with dihedral angles of 89.7 (3)° for the N-O-Cmeth-yl group in (1), 71.01 (4) and 80.00 (4)° for the N-O-C(=O)O-Cmeth-yl groups in (2), and 75.62 (14) and 74.13 (4)° for the same groups in (3). In the crystal of (1), there are unusual inter-molecular C=O⋯C contacts of 2.794 (1) and 2.873 (1) Å present in mol-ecules A and B, respectively. There are also C-H⋯O hydrogen bonds and π-π inter-actions [inter-centroid distance = 3.407 (3) Å] present, forming slabs lying parallel to (001). In the crystal of (2), the A and B mol-ecules are linked by C-H⋯O hydrogen bonds, forming slabs parallel to (10-1), which are in turn linked via a number of π-π inter-actions [the most significant centroid-centroid distances are 3.4202 (7) and 3.5445 (7) Å], forming a three-dimensional structure. In the crystal of (3), the A and B mol-ecules are linked via C-H⋯O hydrogen bonds, forming a three-dimensional structure, which is consolidated by π-π inter-actions [the most significant inter-centroid distances are 3.575 (3) and 3.578 (3) Å].

No MeSH data available.


Related in: MedlinePlus