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Crystal structure of 4,5-di ­ bromo ­ phenanthrene

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ABSTRACT

The synthesis and crystal structure of the title compound, C14H8Br2, is described. The mol­ecule is positioned on a twofold rotation axis and the asymmetric unit consists of half a mol­ecule with the other half being generated by symmetry. The presence of two large bromine atoms in the bay region significantly distorts the mol­ecule from planarity and the mean planes of the two terminal rings of the phenanthrene system are twisted away from each other by 28.51 (14)°. The torsion angle between the two C—Br bonds is 74.70 (14)° and the distance between the two Br atoms is 3.2777 (13) Å. The mol­ecules pack in layers in the crystal, with the centroids of the central rings of the phenanthrene units in adjacent layers separated by a distance of 4.0287 (10) Å. These centroids are shifted by 2.266 (6) Å relative to each other, indicating slippage in the stacking arrangement. Furthermore, the distance between the centroids of the terminal and central rings of the phenanthrene units in adjacent layers is slightly shorter at 3.7533 (19) Å. While all of the mol­ecules within each layer are oriented in the same direction, those in adjacent layers are oriented in the opposite direction, leading to anti-parallel stacks.

No MeSH data available.


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Crystal packing of 2 when viewed along the b axis. The separation between the centroids of the middle rings (blue spheres) is slightly longer than that between the centroids of the middle and terminal rings (blue and orange spheres) in adjacent layers. Close contacts are also observed between equivalent carbon atoms in the terminal rings (shown in green) that are offset from each other. All lengths are in Å.
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fig4: Crystal packing of 2 when viewed along the b axis. The separation between the centroids of the middle rings (blue spheres) is slightly longer than that between the centroids of the middle and terminal rings (blue and orange spheres) in adjacent layers. Close contacts are also observed between equivalent carbon atoms in the terminal rings (shown in green) that are offset from each other. All lengths are in Å.

Mentions: A view of the crystal packing diagram, along the b axis, shows the centroids of the central B rings of the phenanthrene units in adjacent layers (marked in blue in Fig. 4 ▸, see Fig. 3 ▸ for ring numbering), separated by a distance of 4.0287 (10) Å. These (blue) centroids are shifted by 2.266 (6) Å relative to each other, indicating a slippage in the stacking arrangement. This ring slippage is also evidenced by the centroid of the B ring being at a shorter distance of 3.7533 (19) Å to the A ring centroid (shown in orange in Fig. 4 ▸) of the closest phenanthrene unit in an adjacent layer. In addition, short contacts of 3.328 (5) Å are found between C6 (or C6′; refer to Fig. 2 ▸. for atom numbering) and an equivalent carbon atom in an adjacent layer. These atoms, which are in terminal rings offset from each other, are shown in green in Fig. 4 ▸. A view along the a axis (Fig. 5 ▸) shows the opposing orientation of the mol­ecules in going from one layer to the next, leading to anti-parallel stacks.


Crystal structure of 4,5-di ­ bromo ­ phenanthrene
Crystal packing of 2 when viewed along the b axis. The separation between the centroids of the middle rings (blue spheres) is slightly longer than that between the centroids of the middle and terminal rings (blue and orange spheres) in adjacent layers. Close contacts are also observed between equivalent carbon atoms in the terminal rings (shown in green) that are offset from each other. All lengths are in Å.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5382617&req=5

fig4: Crystal packing of 2 when viewed along the b axis. The separation between the centroids of the middle rings (blue spheres) is slightly longer than that between the centroids of the middle and terminal rings (blue and orange spheres) in adjacent layers. Close contacts are also observed between equivalent carbon atoms in the terminal rings (shown in green) that are offset from each other. All lengths are in Å.
Mentions: A view of the crystal packing diagram, along the b axis, shows the centroids of the central B rings of the phenanthrene units in adjacent layers (marked in blue in Fig. 4 ▸, see Fig. 3 ▸ for ring numbering), separated by a distance of 4.0287 (10) Å. These (blue) centroids are shifted by 2.266 (6) Å relative to each other, indicating a slippage in the stacking arrangement. This ring slippage is also evidenced by the centroid of the B ring being at a shorter distance of 3.7533 (19) Å to the A ring centroid (shown in orange in Fig. 4 ▸) of the closest phenanthrene unit in an adjacent layer. In addition, short contacts of 3.328 (5) Å are found between C6 (or C6′; refer to Fig. 2 ▸. for atom numbering) and an equivalent carbon atom in an adjacent layer. These atoms, which are in terminal rings offset from each other, are shown in green in Fig. 4 ▸. A view along the a axis (Fig. 5 ▸) shows the opposing orientation of the mol­ecules in going from one layer to the next, leading to anti-parallel stacks.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The synthesis and crystal structure of the title compound, C14H8Br2, is described. The mol­ecule is positioned on a twofold rotation axis and the asymmetric unit consists of half a mol­ecule with the other half being generated by symmetry. The presence of two large bromine atoms in the bay region significantly distorts the mol­ecule from planarity and the mean planes of the two terminal rings of the phenanthrene system are twisted away from each other by 28.51 (14)°. The torsion angle between the two C—Br bonds is 74.70 (14)° and the distance between the two Br atoms is 3.2777 (13) Å. The mol­ecules pack in layers in the crystal, with the centroids of the central rings of the phenanthrene units in adjacent layers separated by a distance of 4.0287 (10) Å. These centroids are shifted by 2.266 (6) Å relative to each other, indicating slippage in the stacking arrangement. Furthermore, the distance between the centroids of the terminal and central rings of the phenanthrene units in adjacent layers is slightly shorter at 3.7533 (19) Å. While all of the mol­ecules within each layer are oriented in the same direction, those in adjacent layers are oriented in the opposite direction, leading to anti-parallel stacks.

No MeSH data available.


Related in: MedlinePlus