1-Diazonaphthalen-2(1H)-one

The molecule of the title compound, C10H6N2O, is nearly planar [maximum deviation = 0.030 (1) Å]. The CN2 moiety is almost linear, with a C—N—N angle of 175.50 (14)°. A single intermolecular C—H⋯O hydrogen bond is observed in the crystal structure. A π–π interaction is also observed with the shortest distance being 3.6832 (12) Å between the the centroids of the six-membered rings.

The molecule of the title compound, C 10 H 6 N 2 O, is nearly planar [maximum deviation = 0.030 (1) Å ]. The CN 2 moiety is almost linear, with a C-N-N angle of 175.50 (14) . A single intermolecular C-HÁ Á ÁO hydrogen bond is observed in the crystal structure. Ainteraction is also observed with the shortest distance being 3.6832 (12) Å between the the centroids of the six-membered rings.

Structure Reports Online
In the structure of the title compound ( Fig. 1) the CN 2 moiety is almost linear, with C1-N1-N2 = 175.50 (14) is close to a double bond. These data suggest that the structure of the title compound is not diazonium naphtholate form in the solid state.
A single intermolecular hydrogen bond is observed C6-H3···O1 i is observed in the crystal structure (Fig. 2). In addition, a π -π interaction is obserbed with the shotest distance 3.6832 (12) Å between the the centroids of the six memberd rings.
2-Naphthol (130 mg, 0.90 mmol) and triethylamine (0.25 ml, 1.8 mmol) in THF (4 ml) were added to the mixture, which was stirred for 20 min. The reaction was quenched with water, and organic materials were extracted three times with CH 2 Cl 2 .
The combined extracts were washed with water and brine, and then, dried over anhydrous sodium sulfate. The solvent was removed in vacuo to afford crude compound. The crude material was purified by flash column chromatography (silica gel: hexane/ethyl acetate = 4/1) to give the title compound in 86% yield. Single-crystals suitable for X-ray crystallographic analysis were obtained by recrystallization from a mixture of hexane and ethyl acetate (5:1).