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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 B in compound (2), perpendicular inter­actions between atoms O1B and C9B (shown as dashed lines) link the mol­ecules into inversion dimers [symmetry code: (A) −x, −y + 1, −z − 1].
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fig7: For mol­ecule B in compound (2), perpendicular inter­actions between atoms O1B and C9B (shown as dashed lines) link the mol­ecules into inversion dimers [symmetry code: (A) −x, −y + 1, −z − 1].

Mentions: Inter­estingly, in the crystal of (2) one of the two dione moieties for each mol­ecule (O1A and O1B) has a short inter­molecular inter­actions with the central C atom of the carbonato group [O1A⋯C9A = 2.794 (1), O1B⋯C9B = 2.873 (1) Å], which is perpendicular to the carbonato plane indicating that both atoms, C9A and C9B, must have significant positive character. These inter­actions link the mol­ecules into dimers as shown in Figs. 6 ▶ and 7 ▶, respectively. This is also noticed to a lesser extent in (3) (Fig. 8 ▶) for mol­ecule A (but not for mol­ecule B), where a longer inter­molecular inter­action of 3.060 (3) Å is observed between atoms O2A and C13A, resulting in weakly associated dimers similar to that seen in the case of (2).


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 B in compound (2), perpendicular inter­actions between atoms O1B and C9B (shown as dashed lines) link the mol­ecules into inversion dimers [symmetry code: (A) −x, −y + 1, −z − 1].
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig7: For mol­ecule B in compound (2), perpendicular inter­actions between atoms O1B and C9B (shown as dashed lines) link the mol­ecules into inversion dimers [symmetry code: (A) −x, −y + 1, −z − 1].
Mentions: Inter­estingly, in the crystal of (2) one of the two dione moieties for each mol­ecule (O1A and O1B) has a short inter­molecular inter­actions with the central C atom of the carbonato group [O1A⋯C9A = 2.794 (1), O1B⋯C9B = 2.873 (1) Å], which is perpendicular to the carbonato plane indicating that both atoms, C9A and C9B, must have significant positive character. These inter­actions link the mol­ecules into dimers as shown in Figs. 6 ▶ and 7 ▶, respectively. This is also noticed to a lesser extent in (3) (Fig. 8 ▶) for mol­ecule A (but not for mol­ecule B), where a longer inter­molecular inter­action of 3.060 (3) Å is observed between atoms O2A and C13A, resulting in weakly associated dimers similar to that seen in the case of (2).

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