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Crystal structure of (E)-4-{2-[4-(all-yloxy)phen-yl]diazen-yl}benzoic acid.

Rahman ML, Mohd Yusoff M, Ismail J, Kwong HC, Quah CK - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: The two disordered components of the carb-oxy-lic acid group make dihedral angles of 1.5 (14) and 3.8 (12)° with the benzene ring to which they are attached.The dimers are connected via C-H⋯O hydrogen bonds, forming ribbons lying parallel to [120].These ribbons are linked via C-H⋯π inter-actions, forming slabs parallel to (001).

View Article: PubMed Central - HTML - PubMed

Affiliation: University Malaysia Pahang, Faculty of Industrial Sciences and Technology, 26300 Gambang, Kuantan, Pahang, Malaysia.

ABSTRACT
The title compound, C16H14N2O3, has an E conformation about the azo-benzene [-N=N- = 1.2481 (16) Å] linkage. The benzene rings are almost coplanar [dihedral angle = 1.36 (7)°]. The O atoms of the carb-oxy-lic acid group are disordered over two sets of sites and were refined with an occupancy ratio of 0.5:0.5. The two disordered components of the carb-oxy-lic acid group make dihedral angles of 1.5 (14) and 3.8 (12)° with the benzene ring to which they are attached. In the crystal, mol-ecules are linked via pairs of O-H⋯O hydrogen bonds, forming inversion dimers. The dimers are connected via C-H⋯O hydrogen bonds, forming ribbons lying parallel to [120]. These ribbons are linked via C-H⋯π inter-actions, forming slabs parallel to (001).

No MeSH data available.


Related in: MedlinePlus

The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. Only one component of the disordered carb­oxy­lic acid group is shown.
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fig1: The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. Only one component of the disordered carb­oxy­lic acid group is shown.

Mentions: The mol­ecular structure of the title mol­ecule is illustrated in Fig. 1 ▶. The oxygen atoms forming the carb­oxy­lic acid group are each disordered over two positions and were refined with half occupancy. The carb­oxy­lic acid group (C16/O2/O3) is almost coplanar with the attached benzene ring (C10–C15), making dihedral angles of 3.44 (9) and 3.65 (8)° for the two disorder components. The title compound has an E conformation about the azo­benzene (—N=N—) linkage, the length of the N1—N2 bond is 1.2481 (16) Å and the torsion angle for the azo unit (C7—N1=N2—C10) is 179.99 (10)°, which is comparable with the values of ca ±180° observed in 4,4-azinodi­benzoic acid (Yu & Liu, 2009 ▶) and (E)-ethyl-4-{[4-(deca­noxl­oxy)phen­yl]diazenly} benzoate (Lai et al., 2002 ▶). The benzene rings (C4–C9) and (C10–C15) are almost coplanar, making a dihedral angle of 1.38 (7)°, compared with 6.79 (9)° in the previously reported compound 4-{(E)-2-[4-(but-3-en-1-yl­oxy)phen­yl]-diazen-1-yl}benzoic acid, (Rahman et al., 2012 ▶).


Crystal structure of (E)-4-{2-[4-(all-yloxy)phen-yl]diazen-yl}benzoic acid.

Rahman ML, Mohd Yusoff M, Ismail J, Kwong HC, Quah CK - Acta Crystallogr Sect E Struct Rep Online (2014)

The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. Only one component of the disordered carb­oxy­lic acid group is shown.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257410&req=5

fig1: The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. Only one component of the disordered carb­oxy­lic acid group is shown.
Mentions: The mol­ecular structure of the title mol­ecule is illustrated in Fig. 1 ▶. The oxygen atoms forming the carb­oxy­lic acid group are each disordered over two positions and were refined with half occupancy. The carb­oxy­lic acid group (C16/O2/O3) is almost coplanar with the attached benzene ring (C10–C15), making dihedral angles of 3.44 (9) and 3.65 (8)° for the two disorder components. The title compound has an E conformation about the azo­benzene (—N=N—) linkage, the length of the N1—N2 bond is 1.2481 (16) Å and the torsion angle for the azo unit (C7—N1=N2—C10) is 179.99 (10)°, which is comparable with the values of ca ±180° observed in 4,4-azinodi­benzoic acid (Yu & Liu, 2009 ▶) and (E)-ethyl-4-{[4-(deca­noxl­oxy)phen­yl]diazenly} benzoate (Lai et al., 2002 ▶). The benzene rings (C4–C9) and (C10–C15) are almost coplanar, making a dihedral angle of 1.38 (7)°, compared with 6.79 (9)° in the previously reported compound 4-{(E)-2-[4-(but-3-en-1-yl­oxy)phen­yl]-diazen-1-yl}benzoic acid, (Rahman et al., 2012 ▶).

Bottom Line: The two disordered components of the carb-oxy-lic acid group make dihedral angles of 1.5 (14) and 3.8 (12)° with the benzene ring to which they are attached.The dimers are connected via C-H⋯O hydrogen bonds, forming ribbons lying parallel to [120].These ribbons are linked via C-H⋯π inter-actions, forming slabs parallel to (001).

View Article: PubMed Central - HTML - PubMed

Affiliation: University Malaysia Pahang, Faculty of Industrial Sciences and Technology, 26300 Gambang, Kuantan, Pahang, Malaysia.

ABSTRACT
The title compound, C16H14N2O3, has an E conformation about the azo-benzene [-N=N- = 1.2481 (16) Å] linkage. The benzene rings are almost coplanar [dihedral angle = 1.36 (7)°]. The O atoms of the carb-oxy-lic acid group are disordered over two sets of sites and were refined with an occupancy ratio of 0.5:0.5. The two disordered components of the carb-oxy-lic acid group make dihedral angles of 1.5 (14) and 3.8 (12)° with the benzene ring to which they are attached. In the crystal, mol-ecules are linked via pairs of O-H⋯O hydrogen bonds, forming inversion dimers. The dimers are connected via C-H⋯O hydrogen bonds, forming ribbons lying parallel to [120]. These ribbons are linked via C-H⋯π inter-actions, forming slabs parallel to (001).

No MeSH data available.


Related in: MedlinePlus