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(E)-4-Allyl-2-[(2-hydroxy-phen-yl)iminiometh-yl]-6-methoxy-phenolate.

ABSTRACT: The title compound, C(17)H(17)NO(3), crystallizes in a zwitterionic form with cationic iminium and anionic enolate groups. The zwitterion exists in a trans configuration about the C=N bond. The dihedral angle between the two benzene rings is 13.42 (7)°. The meth-oxy group is almost coplanar [C-O-C-C = 2.1 (2)°] with the attached ring whereas the allyl unit is oriented at a dihedral angle of 67.9 (1)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the mol-ecules are linked into zigzag chains along [010] by O-H⋯O hydrogen bonds. In addition, weak C-H⋯π inter-actions are observed.

SUBMITTER: Eltayeb NE

PROVIDER: S-EPMC2983958 | biostudies-literature |

REPOSITORIES: biostudies-literature

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(E)-2-[(2-Hydroxy-ethyl)iminiometh-yl]-6-methoxy-phenolate.

Project description:The title Schiff base compound, C(10)H(13)NO(3), obtained by the reaction of 2-hydr-oxy-3-methoxy-benzaldehyde and 2-amino-ethanol in methanol solution, crystallizes in a zwitterionic form, in which the mol-ecule adopts a trans configuration about the central C=N bond. An intra-molecular N-H?O hydrogen bond occurs. In the crystal structure, mol-ecules are linked into chains by inter-molecular O-H?O hydrogen bonding.

| S-EPMC2968608 | biostudies-literature

(E)-4-Bromo-2-[(2-hydroxy-phen-yl)iminiometh-yl]phenolate.

Project description:The title compound, C(13)H(10)BrNO(2), crystallizes in a zwitterionic form. The zwitterion exists in a trans configuration about the C=N bond and is almost planar, the dihedral angle between the two benzene rings being 2.29?(9)°. An intra-molecular N-H?O hydrogen bond formed between the iminium NH(+) and the phenolate O(-) atoms generates an S(6) ring motif. In the crystal, the zwitterions are linked through O-H?O hydrogen bonds into chains along [101] and these chains are further connected through C-H?Br inter-actions into a two-dimensional network perpendicular to (101). C?C [3.572?(3)-3.592?(3)?Å] and C?Br [3.5633?(19)-3.7339?(18)?Å] short contacts are observed. The crystal studied was a twin with twin law 00, 00, 001 with a domain ratio of 0.09919?(2):0.90081?(2).

| S-EPMC2979394 | biostudies-literature

(E)-2-[(2-Ethyl-phen-yl)iminiometh-yl]-6-hydroxy-phenolate.

Project description:The mol-ecule of the title compound, C(15)H(15)NO(2), crystallizes in a zwitterionic form, and displays an E configuration about the C=N bond. The dihedral angle between the two aromatic rings is 5.59?(6)°. An intra-molecular N-H?O hydrogen bond generates an S(6) ring motif. In the crystal structure, pairs of mol-ecules are linked into centrosymmetric R(2) (2)(10) dimers by pairs of O-H?O hydrogen bonds. Aromatic ?-? inter-actions are observed between the benzene rings of adjacent dimers [centroid-centroid distance = 3.4808?(7)?Å].

| S-EPMC2979895 | biostudies-other

2-((E)-{2-[(E)-2,3-Dihydroxy-benzyl-ideneamino]-5-methyl-phen-yl}iminiometh-yl)-6-hydroxy-phenolate.

Project description:The asymmetric unit of the title Schiff base compound, C(21)H(18)N(2)O(4), consists of four independent zwitterions (A, B, C and D) with similar conformations. In each independent mol-ecule, the methyl group is disordered over two positions; the occupancies of the two positions are 0.819 (5) and 0.181 (5) in mol-ecule A, 0.912 (5) and 0.088 (5) in B, 0.734 (5) and 0.266 (5) in C, and 0.940 (6) and 0.060 (6) in D. The dihydroxy-phenyl and the hydroxy-phenolate rings in mol-ecule A form dihedral angles of 17.36 (12) and 13.30 (12)°, respectively, with the central benzene ring, whereas the respective angles for mol-ecules B, C and D are 30.22 (11)/7.46 (11), 35.26 (12)/11.01 (12) and 39.89 (12)/4.29 (12)°. In all independent mol-ecules, intra-molecular N-H⋯O and O-H⋯N hydrogen bonds generate S(6) ring motifs. The four independent mol-ecules are linked into two pairs, viz. A-B and C-D, by inter-molecular O-H⋯O hydrogen bonds. These pairs are linked into a two-dimensional network parallel to the ab plane by C-H⋯O hydrogen bonds. In addition, C-H⋯π and π-π [centroid-centroid distance = 3.5153 (14)-3.7810 (15) Å] inter-actions stabilize the crystal structure.

| S-EPMC2969866 | biostudies-literature

2-((E)-{2-[(1E)-(2,4-Dihydroxy-benzyl-idene)amino]phen-yl}iminiometh-yl)-5-hydroxy-phenolate methanol solvate.

Project description:The asymmetric unit of the title compound, C(20)H(16)N(2)O(4)·CH(3)OH, contains two Schiff base zwitterions and two methanol solvent mol-ecules. The dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base are 2.57 (7) and 52.30 (7)° in one mol-ecule and 5.83 (7) and 49.82 (7)° in the other mol-ecule. Intra-molecular O-H⋯N and N-H⋯O hydrogen bonds generate S(6) ring motifs, whereas intra-molecular N-H⋯N hydrogen bonds generate S(5) ring motifs. In the crystal structure, O-H⋯O, hydrogen bonds and weak C-H⋯O inter-actions link the mol-ecules into one-dimensional chains along the b-axis direction and are further connected by O-H⋯O and weak C-H⋯O inter-actions into a three-dimensional network. C-H⋯π and π-π inter-actions [centroid-centroid distances = 3.6228 (9) and 3.6881 (9) Å] are also observed in the crystal structure.

| S-EPMC2961737 | biostudies-literature

(E)-2-[(2-Hydr-oxy-5-nitro-phen-yl)iminiometh-yl]phenolate.

Project description:In the title mol-ecule, C(13)H(10)N(2)O(4), the dihedral angle between the mean planes of the benzene and phenolate rings is 21.6?(4)°. The nitro O atoms are twisted slightly out of the plane of the ring to which the nitro group is attached [dihedral angle 8.4?(3)°]. The amine group forms an intra-molecular hydrogen bond with both nearby O atoms. An extended ? delocalization throughout the entire mol-ecule exists producing a zwitterionic effect in this region of the mol-ecule. The shortened C-O bond [1.2997?(15)?Å] in concert with the slightly longer C-OH bond [1.3310?(16)?Å] provide evidence for this effect. The crystal packing is influenced by strong inter-molecular O-H?O hydrogen bonding. As a result, mol-ecules are linked into an infinite zigzag chain running along the b axis. A MOPAC PM3 calculation provides support to these observations.

| S-EPMC2968543 | biostudies-literature

(E)-4-Hy-droxy-2-[(2-hy-droxy-phen-yl)iminiometh-yl]phenolate.

Project description:The title compound, C(13)H(11)NO(3), crystallizes in a zwitterionic form and has a trans configuration about the C=N bond. The mol-ecule is almost planar, the dihedral angle between the two benzene rings being 4.32?(8)°. The two hy-droxy substit-uents are coplanar with each of their attached benzene rings [r.m.s. deviations of 0.0053?(2) and 0.0052?(2)?Å]. An intra-molecular N-H?O hydrogen bond formed between the iminium N and the phenolate O atom generates an S(6) ring motif. In the crystal, the mol-ecules are linked through O-H?O hydrogen bonds into chains along [110]. Two neighbouring chains are further connected through O-H?O hydrogen bonds in an anti-parallel manner. ?-? inter-actions are also observed, with centroid-centroid distances of 3.7115?(19) and 3.743?(2)?Å.

| S-EPMC3006709 | biostudies-literature

2-[(E)-(3-Carb-oxy-4-hy-droxy-phen-yl)iminiometh-yl]-4-chloro-phenolate.

Project description:The title Schiff base compound, C(14)H(10)ClNO(4), has been synthesized by the reaction of 5-amino-2-hy-droxy-benzoic acid and 5-chloro-2-hy-droxy-benzaldehyde. The mol-ecule is a zwitterion in the crystal, with the phenolic hy-droxy group deprotonated and the imine N atom protonated. It adopts an E configuration about the central C=N double bond. The dihedral angle between the two benzene rings is 3.83 (7)°. Intra-molecular N-H⋯O and O-H⋯O hydrogen bonding generates S(6) ring motifs. In the crystal, mol-ecules are connected by inter-molecular O-H⋯O and C-H⋯Cl hydrogen bonds, forming a supra-molecular chain.

| S-EPMC3007861 | biostudies-literature

Ethyl 3-(4-hydroxy-phen-oxy)-2-(4-methoxy-phen-yl)acrylate.

Project description:In the title compound, C(18)H(18)O(5), the dihedral angle between the two benzene rings is 55.2 (3)°. The ethyl acrylate linkage is planar and forms dihedral angles of 21.3 (3) and 41.0 (3)°, respectively, with the hydroxy-phenyl and methoxy-phenyl rings. In the crystal structure, mol-ecules are linked into zigzag chains along the b axis by O-H⋯O hydrogen bonds.

| S-EPMC2959932 | biostudies-literature

Low-temperature redetermination of 4-chloro-2-[tris-(hydroxy-meth-yl)methyl-imino-meth-yl]phenol as zwitterionic 4-chloro-2-[tris-(hydroxy-meth-yl)methyl-iminiometh-yl]phenolate.

Project description:The title Schiff base, C(11)H(14)ClNO(4), originally refined as a neutral mol-ecule [Chumakov, Antosyak, Mazus, Tsapkov & Samus (2000), Crystallogr. Rep.45, 945-950], is inter-preted as a zwitterionic compound. There are two independent zwitterions in the asymmetric unit. Five of the six hydr-oxy groups of the -CH(2)OH fragments are disordered. In one zwitterion, two are disordered over three sites [0.53 (1):0.33 (1):0.14 (1) and 0.65 (1):0.18 (1):0.17 (1)] and the third over two sites [0.66 (1):0.34 (1)]. In the second zwitterion, two are disordered over two sites [0.84 (1):0.16 (1) and 0.83 (1):0.17 (1)] and the third hydr-oxy group is ordered.

| S-EPMC2960041 | biostudies-literature

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