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Crystal structure of 4,4 ′ -di ­ nitro-[1,1 ′ -biphen ­ yl]-2-amine

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ABSTRACT

In the title biphenyl derivative, C12H9N3O4, the dihedral angle between the benzene rings is 52.84 (10)°. The nitro group attached to the benzene ring is inclined to the ring by 4.03 (2)°, while the nitro group attached to the amino-substituted benzene ring is inclined to the ring by 8.84 (2)°. In the crystal, mol­ecules are linked by two pairs of N—H⋯O hydrogen bonds, forming chains propagating along [101]. Within the chains, these N—H⋯O hydrogen bonds result in the formation of R22(20) and R22(14) ring motifs. The latter ring motif is reinforced by a pair of C—H⋯O hydrogen bonds, enclosing R21(6) ring motifs. The chains are linked by a second C—H⋯O hydrogen bond, forming a three-dimensional supra­molecular structure.

No MeSH data available.


The mol­ecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 40% probability level.
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fig1: The mol­ecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 40% probability level.

Mentions: The mol­ecular structure of the title compound (I), is illus­trated in Fig. 1 ▸. The dihedral angle between the two rings of the biphenyl unit is 52.84 (10)°. The nitro group (N3/O3/O4) is inclined to the benzene ring (C7–C12) to which it is attached by 4.03 (2)°. The nitro group (N1/O1/O2) is inclined to the amino-substituted benzene ring (C1–C6), to which it is attached, by 8.84 (2)°. The amino N atom, N2, lies in the plane of the C1–C6 benzene ring, and the N2—C5 bond length of 1.375 (3) Å clearly indicates a single bond. The C1—N1 distance of 1.466 (3) Å is slightly less than the C10—N3 bond distance of 1.477 (3) Å, which indicates that the 2-amino group containing a benzene ring (C1–C6) is more conjugated with the nitro group (N1/O1/O2) than is the other nitro group (N3/O3/O4) with respect to the C7–C12 benzene ring. The bond length of the C4—C7 bridge is 1.482 (3) Å, which indicates a single bond, and is similar to the same bond length of 1.494 (2) Å reported for dimethyl 2,2′-di­nitro­biphenyl-4,4′-di­carboxyl­ate (Lehane et al., 2014 ▸), and ca 1.493 Å observed in 2,2′-di­nitro­biphenyl (Sekine et al., 1994 ▸).


Crystal structure of 4,4 ′ -di ­ nitro-[1,1 ′ -biphen ­ yl]-2-amine
The mol­ecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 40% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5382619&req=5

fig1: The mol­ecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 40% probability level.
Mentions: The mol­ecular structure of the title compound (I), is illus­trated in Fig. 1 ▸. The dihedral angle between the two rings of the biphenyl unit is 52.84 (10)°. The nitro group (N3/O3/O4) is inclined to the benzene ring (C7–C12) to which it is attached by 4.03 (2)°. The nitro group (N1/O1/O2) is inclined to the amino-substituted benzene ring (C1–C6), to which it is attached, by 8.84 (2)°. The amino N atom, N2, lies in the plane of the C1–C6 benzene ring, and the N2—C5 bond length of 1.375 (3) Å clearly indicates a single bond. The C1—N1 distance of 1.466 (3) Å is slightly less than the C10—N3 bond distance of 1.477 (3) Å, which indicates that the 2-amino group containing a benzene ring (C1–C6) is more conjugated with the nitro group (N1/O1/O2) than is the other nitro group (N3/O3/O4) with respect to the C7–C12 benzene ring. The bond length of the C4—C7 bridge is 1.482 (3) Å, which indicates a single bond, and is similar to the same bond length of 1.494 (2) Å reported for dimethyl 2,2′-di­nitro­biphenyl-4,4′-di­carboxyl­ate (Lehane et al., 2014 ▸), and ca 1.493 Å observed in 2,2′-di­nitro­biphenyl (Sekine et al., 1994 ▸).

View Article: PubMed Central - HTML - PubMed

ABSTRACT

In the title biphenyl derivative, C12H9N3O4, the dihedral angle between the benzene rings is 52.84 (10)°. The nitro group attached to the benzene ring is inclined to the ring by 4.03 (2)°, while the nitro group attached to the amino-substituted benzene ring is inclined to the ring by 8.84 (2)°. In the crystal, mol­ecules are linked by two pairs of N—H⋯O hydrogen bonds, forming chains propagating along [101]. Within the chains, these N—H⋯O hydrogen bonds result in the formation of R22(20) and R22(14) ring motifs. The latter ring motif is reinforced by a pair of C—H⋯O hydrogen bonds, enclosing R21(6) ring motifs. The chains are linked by a second C—H⋯O hydrogen bond, forming a three-dimensional supra­molecular structure.

No MeSH data available.