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Updated: May 7, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
1-(2,4-Di-nitro-phen-yl)-2-[(E)-2,4,5-tri-meth-oxy-benzyl-idene]hydrazine
Hoong-Kun Fun1, Suchada Chantrapromma, Boonlerd Nilwanna
1X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
Abstract:
The title compound, C16H16N4O7, is close to being planar, with a dihedral angle of 3.15 (11)° between the benzene rings. The meth-oxy groups at the ortho- and para-positions of the 2,4,5-tri-meth-oxy-phenyl group are almost coplanar with the ring [deviations of the C atoms = 0.017 (2) and -0.025 (2) Å, respectively], whereas the meta-meth-oxy group deviates slightly [C-atom displacement = 0.162 (2) Å]. Both the ortho- and para-nitro groups are close to being coplanar with their attached ring [dihedral angles = 7.81 (12) and 8.56 (11)°, respectively]. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds involving the same H atom as the intra-molecular bond generate R 2 (2)(12) loops. The dimers are linked by weak C-H⋯O inter-actions into sheets parallel to the (10-4) plane and the sheets are stacked by π-π inter-actions, with a centroid-centroid distance of 3.5974 (14) Å.
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