Structure of the photostable form of p-nitrocinnamic acid

Abstract

The molecule is planar to within 0.08 (2)/~. The molecules form a centrosymmetric dimer through O--H...O hydrogen bonds between the carboxylic groups. The dimers are stacked along b with an interplanar distance of 3.374 (2) A. The C--C double bonds of the nearest neighbors are related by a b translation. CommentThe structure of the photostable form of pnitrocinnamic acid has been determined as part of studies into solid-state photoreactions (Iwamoto, Kashino & Haisa, 1989). The lattice parameters and space groups of the photostable and photoreactive forms of the title compound have been reported by Schmidt (1964). The crystals used in the present study were obtained by slow evaporation from an ethanol solution. The crystal structure is similar to t On leave from Kobe Women's University Seto Junior College, Seto, Akaiwa, Okayama 709-08, Japan.o (1 ) C (

3-Nitrocinnamic acid

“…The angle between the mean plane of the benzene ring and the mean plane of the propenoic acid moiety is 3.5 (7) in (I) and 2.6 in 4-dimethylamino-3-nitrocinnamic acid (Huber, 1985). The corresponding angles in 4-chlorocinnamic acid (Glusker et al, 1975), 4-iodocinnamic acid (Goud et al, 1993), p-nitrocinnamic acid (Kageyama et al, 1993), 3,5-dinitrocinnamic acid and the 3,5-dinitrocinnamic acid 2,5dimethoxycinnamic acid complex (Desiraju & Sharma, 1991) are 14.1, 13.8, 4.7, 28.7 and 6.4 , respectively. In the 3,5dinitrocinnamic acid 4-(N,N-dimethylamino)cinnamic acid complex, the propenoic acid group is twisted by 7.6 out of the mean plane of the benzene ring (Sharma et al, 1993).…”

“…In a related structure, viz. p-nitrocinnamic acid (Kageyama et al, 1993), the nitro group is coplanar (2.2 ) with the benzene ring. With respect to the plane of the benzene ring, the 3-nitro group is oriented at an angle of 45.3 in 4-dimethylamino-3-nitrocinnamic acid (Huber, 1985), 3.6 in 3,5-dinitrocinnamic acid and 2.3 in the 3,5-dinitrocinnamic acid 2,5-dimethoxycinnamic acid complex (Desiraju & Sharma, 1991), 3.0 in the 3,5-dinitrocinnamic acid 4-(N,N-dimethylamino)benzoic acid complex and 6.1 in the 3,5-dinitrocinnamic acid 4-(N,N-dimethylamino)cinnamic acid complex (Sharma et al, 1993).…”

4-(Acetylamino)-3-hydroxy-5-nitrobenzoic Acid

“…CO2H, NO2, OH and C2HnNO, are also listed in Table 2. The crystal structure of the title compound is similar to other phenyl-ring-based structures (Bryan, Hartley, Peckler, Fujita, Nagao & Seno, 1980;Bums & Hagaman, 1993;Carpy, Goursolle & Leger, 1980;Gozlan & Riche, 1976;Kageyama, Iwamoto, Haisa & Kashino, 1993;Metzger, Laidlaw, Torres & Panetta, 1989;Metzger, Atwood, Lee, Rao, Lal & Loo, 1993;Nielsen & Larsen, 1993;Okabe, 1993;Okabe, Nakamura & Fukuda, 1993;Soundararajan, Duesler & Hageman, 1993). …”

Synthesis and crystal structures of two isomeric nitro-α-resorcylic acids

“…Additionally, molecular dimers are stacked by dispersive pÁÁÁp interactions between benzene rings of one dimer and nitro and carboxyl groups of the parallel adjacent dimer separated by 3.3-3.4 Å . Together with the NÁÁÁO interactions, this results in the fish-bone pattern of the crystal packing, also observed in the crystal structures of similar compounds: p-nitrobenzoic acid [25,26], p-nitrocinnamic acid [27], and p-nitrobenzene [28].…”