2-Hydroxy-5-{[( E )-4-methoxybenzylidene]azaniumyl}benzoate

Shad²

2010

Self Cite

The zwitterionic title compound, C16H12N2O3, was obtained as a result of the condensation of 5-aminosalicylic acid and 1H-indole-3-carbaldehyde. The whole molecule is roughly planar: the 4-hydroxyanilinic group and the 1H-indole-3-carbaldehyde moieties are only slightly twisted, making a dihedral angle of 7.77 (11)°, whereas, the carboxylate group makes a dihedral angle of 3.34 (45)° with the parent 4-hydroxyanilinic group. S(6) ring motifs are formed due to intramolecular O—H⋯O hydrogen bonding. In the crystal, intermolecular N—H⋯O and C—H⋯O hydrogen bonds build up pseudo-rings with R 1 2(4), R 2 1(7) and R 2 2(14) ring motifs. These pseudo-dimers are further linked by N—H⋯O hydrogen bonds into a chain extending along [101]. C—H⋯π interactions also occur, along with offset π–π interactions between the anilinic phenyl and the heterocyclic five-membered rings with a centroid–centroid distance of 3.5716 (19) Å.

Section: S1 Commentmentioning

confidence: 88%

“…The title compound (I) is Zwitterion similar to 2-hydroxy-5-{[(E)-4-methoxybenzylidene]azaniumyl}benzoate (Tahir et al, 2010b). In (I), the group A (C2-C7/N1/O3) of 5-aminosalicylic acid moiety and the 1H-indole-3-carbaldehyde moiety B (C8-C15/N2) are almost planar with r. m. s. deviations of 0.0258 and 0.0175 Å, respectively (Fig.…”

Section: S1 Commentmentioning

confidence: 99%

2-Hydroxy-5-[(E)-(1H-indol-3-ylmethylidene)azaniumyl]benzoate

Shad²

2010

Self Cite

“…5-[(E)-(2,6-dichlorobenzylidene)amino]-2-hydroxybenzoic acid (Tahir et al, 2010a) and (V) i.e. 2-hydroxy-5-{[(E)-4-methoxybenzylidene]azaniumyl}benzoate (Tahir et al, 2010c). The title compound (I), (Fig.…”

Section: Methodsmentioning

confidence: 99%

5-[(E)-(2-Fluorobenzylidene)amino]-2-hydroxybenzoic acid

Tariq

2011

Self Cite

“…Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON. this context, we have recently reported the synthesis and crystal structure of 2-hydroxy-5-{[(E)-4-methoxybenzylidene]azaniumyl} benzoate (Tahir et al, 2010).…”

mentioning

confidence: 99%

5-[(E)-(2,6-Dichlorobenzylidene)amino]-2-hydroxybenzoic acid

Shad²,

Khan

et al. 2010

Self Cite

There are two geometrically different molecules in the asymmetric unit of the title compound, C14H9Cl2NO3. The 5-amino-2-hydroxybenzoic acid units [r.m.s. deviations of 0.0323 and 0.0414 Å] and 2,6-dichlorobenzaldehyde groups [r.m.s. deviations of 0.0285 and 0.0226 Å] are roughly planar and oriented at dihedral angles of 11.69 (13) and 83.12 (6)° in the two molecules. An intramolecular O—H⋯O hydrogen bond completes an S(6) ring motif in each molecule. The two molecules form dimers with each other through intermolecular O—H⋯N and C—H⋯O hydrogen bonds, completing an R 2 2(8) ring motif. The dimers are interlinked via intermolecular O—H⋯N and C—H⋯O hydrogen bonds, forming polymeric sheets.