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Mol­ecules of the title compound, C18H16O6, are almost planar [maximum deviation = 0.096 (4) Å] and reside on crystallographic centres of inversion. They adopt a conformation in which the Cmeth­yl—O bonds are directed along the mol­ecular short axis [C—C—O—C torsion angles of −175.3 (3) and 178.2 (3)°]. In the crystal, mol­ecules adopt a slipped-parallel arrangement with π–π stacking inter­actions along the a axis with an inter­planar distance of 3.392 (4) Å. Weak C—H...O inter­actions link the mol­ecules into sheets parallel to (10\overline{2}).

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The title compound, C16H12O4, crystallizes with two half-mol­ecules in the asymmetric unit, each of which is completed by a crystallographic inversion center. The two crystallographically independent mol­ecules have almost the same geometry and are almost planar [maximum deviations = 0.018 (3) and 0.049 (3) Å]. They adopt a conformation in which the Cmeth­yl—O bonds are directed along the mol­ecular short axis [C—C—O—C torsion angles of 179.6 (2) and 178.0 (2)°]. In the crystal, the mol­ecular packing is characterized by a combination of a columnar stacking and a herringbone-like arrangement. The mol­ecules form slipped π-stacks along the b axis, in which there are two kinds of columns differing from each other in their slippage. The inter­planar distances between neighboring mol­ecules are 3.493 (3) for one column and 3.451 (2) Å for the other.

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The phenanthrene ring in the title compound, C14H8Br2, is approximately planar [maximum deviation = 0.039 (3) Å]. In contrast, the two bromo atoms are displaced slightly from the phenanthrene plane [maximum deviation = 0.1637 (3) Å]. In the crystal, the mol­ecules adopt a herringbone-like arrangement and form face-to-face slipped π–π stacking inter­actions along the b axis, with an inter­planar distance of 3.544 (3) Å and slippage of 1.81 Å. The crystal studied was a racemic twin with a minor twin fraction of 0.390 (10).

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The mol­ecule of the title compound, C14H8Br2, is almost planar [maximum deviation 0.0355 (7) Å] and possesses crystallographic twofold (C2) symmetry. In the crystal, the mol­ecules form face-to-face slipped anti­parallel π–π stacking inter­actions along the c axis with an inter­planar distance 3.471 (7) Å, centroid–centroid distances of 3.617 (5)–3.803 (6) Å.

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The whole mol­ecule of the title compound, C14H8I2, is generated by crystallographic twofold symmetry. The mol­ecule is planar [maximum deviation = 0.0323 (6) Å] with the I atoms displaced from the mean plane of the phenanthrene ring system by only 0.0254 (5) Å. In the crystal, mol­ecules form face-to-face slipped anti­parallel π–π stacking inter­actions along the c axis with an inter­planar distance of 3.499 (7) Å.
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