Jirapa Horkaew

(E)-N′-(2,3-Dihy­droxy­benzyl­idene)-4-meth­oxy­benzohydrazide

The molecule of the title benzohydrazide derivative, C15H14N2O4, is twisted and exists in a trans conformation with respect to the C=N double bond. The dihedral angle between the benzene rings is 56.86 (9)° and the C atom of the methoxy group deviates slightly [C—O—C—C = −10.4 (3)°] from its attached benzene ring. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring. In the crystal, molecules are linked by N—H⋯O and bifurcated N—H⋯(O,O) hydrogen bonds, as well as weak C—H⋯O interactions, into two-dimensional networks lying parallel to the bc plane. A weak C—H⋯π interaction also occurs.

(E)-4-Bromo-N'-(4-hy-droxy-3-meth-oxy-benzyl-idene)benzohydrazide monohydrate.

In the title compound, C15H13BrN2O3·H2O, the dihedral angle between the two benzene rings is 13.92 (6)°. The methoxy group of the 4-hydroxy-3-methoxyphenyl is almost coplanar with its bound benzene ring, as seen by the Cmethyl—O—C—C torsion angle of −0.35 (16)°. In the crystal, molecules are linked into a three-dimensional network by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds and also weak C—H⋯O interactions. A short C⋯O contact of 3.0191 (15) Å is also present.

(E)-3-(4-Eth-oxy-phen-yl)-1-(2-hy-droxy-phen-yl)prop-2-en-1-one.

In the title compound, C17H16O3, the carbonyl group is in an s-cis configuration with respect to the olefinic double bond. The dihedral angle between the two benzene rings is 2.85 (3)°. The prop-2-en-1-one bridge makes dihedral angles of 4.77 (4) and 4.15 (4)°, respectively, with the 2-hydroxyphenyl and 4-ethoxyphenyl rings. The ethoxy group is coplanar with the attached phenyl ring [Car—O—C—C = 179.72 (5)°]. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, molecules are stacked in an antiparallel manner to form columns along the b axis. The columnar structure is stabilized by C—H⋯π interactions involving the 2-hydroxyphenyl ring.

(Z)-3-(9-Anthr­yl)-1-(4-methoxy­phen­yl)prop-2-en-1-one

The title chalcone derivative, C24H18O2, which consists of the substituted 4-methoxyphenyl and anthracene rings bridged by the prop-2-en-1-one unit, exists in a cis configuration. The molecule is twisted, the interplanar angle between the benzene and anthracene rings being 69.50 (10)°. The methoxy group is coplanar with the attached benzene ring [C—O—C—C angle = 2.9 (3)°]. In the crystal structure, molecules are linked into chains along the a axis by a weak C—H⋯O(enone) interaction. The chains are stacked along the c axis. A C—H⋯π interaction involving the benzene ring is observed.

(E)-N′-(3-Hy­droxy-4-meth­oxy­benzyl­idene)-4-meth­oxy­benzohydrazide

The title molecule, a benzohydrazide derivative, C16H16N2O4, is twisted with a dihedral angle of 69.97 (5)° between the two benzene rings. An intramolecular O—H⋯O hydrogen bond generates an S(5) ring motif. In the crystal, molecules are linked by N—H⋯O and weak C—H⋯O hydrogen bonds into a chain along the c axis. C—H⋯π interactions are also present.

(E)-4-Hy­droxy-N′-(3,4,5-trimeth­oxy­benzyl­idene)benzohydrazide

In the asymmetric unit of the title compound, C18H20N2O5, there are two crystallographic independent molecules. Both molecules are twisted; the dihedral angle between the two benzene rings is 7.2 (5)° in one molecule, whereas it is 85.9 (4)° in the other. Of the three methoxy groups in the 3,4,5-trimethoxyphenyl unit, two methoxy groups at meta positions are approximately coplanar with the benzene plane [C—O—C—C torsion angles of −2.3 (13)–4.8 (11)°], but the other methoxy, at the para position, is out of the plane [C—O—C—C of 72.8 (9)° in one molecule and −77.5 (9)° in the other]. In the crystal, molecules are linked by N—H⋯O hydrogen bonds and weak C—H⋯O interactions into tapes along the b axis. C—H⋯π interactions are also present.

(E)-3-(Anthracen-9-yl)-1-(furan-2-yl)prop-2-en-1-one.

In the molecule of the title heteroaryl chalcone derivative, C21H14O2, the almost planar prop-2-en-1-one unit [r.m.s. deviation = 0.0087 (1) Å] forms dihedral angles of 5.81 (7) and 49.85 (6)°, respectively, with the furan ring and anthracene ring system. In the crystal structure, the molecules are linked into a two-dimensional network parallel to (100) by C—H⋯O hydrogen bonds and π⋯π interactions involving the furan rings [centroid–centroid distance = 3.7205 (6) Å].

Synthesis and antibacterial properties of 4-bromobenzohydrazide derivatives and crystal structure of (E)-N′-((1H-indol-3-yl)methylene)-4-bromobenzohydrazide

Six 4-bromobenzohydrazide derivatives (1–6) were synthesized by the condensation reaction of 4-bromobenzohydrazide and benzaldehydes, and evaluated for antibacterial activity. Their structures were determined by spectroscopic methods. In addition, the crystal structure of compound 6 was characterized by single crystal X-ray structure determination. In crystal packing, the molecules are linked by N–H···O and N–H···N hydrogen bonds into two-dimensional network parallel to the (001) plane. The crystal is further stabilized by weak C–H···O and C–H···π interactions.

(E)-4-Meth­oxy-N′-(2,4,5-tri­meth­oxy­benzyl­idene)benzohydrazide hemihydrate

The title compound crystallizes as a hemihydrate, C18H20N2O5·0.5H2O. The molecule exists in an E conformation with respect to the C=N imine bond. The 4-methoxyphenyl unit is disordered over two sets of sites with a refined occupancy ratio of 0.54 (2):0.46 (2). The dihedral angles between the benzene rings are 29.20 (9) and 26.59 (9)°, respectively, for the major and minor components of the 4-methoxy-substituted ring. All methoxy substituents lie close to the plane of the attached benzene rings [the Cmethyl—O—C—C torsion angles range from −4.0 (12) to 3.9 (2)°]. In the crystal, the components are linked into chains propagating along [001] via N—H⋯O and O—H⋯O hydrogen bonds and weak C—H⋯O interactions.

(E)-N'-(4-Eth-oxy-benzyl-idene)-4-hy-droxy-benzohydrazide dihydrate.

The benzohydrazide molecule of the title compound, C16H16N2O3·2H2O, exists in a trans conformation with respect to the C=N double bond. The central O=C—NH—N=C plane [r.m.s. deviation of 0.0165 (1) Å for the five non-H atoms] makes dihedral angles of 6.04 (8) and 2.38 (8)°, respectively, with the hydroxy- and ethoxy-substituted benzene rings. The dihedral angle between these benzene rings is 3.82 (7)°. The ethoxy group is almost coplanar with the attached benzene ring with a C—O—C—C torsion angle of −176.58 (11)°. In the crystal, the benzohydrazide and water molecules are linked by N—H⋯O, O—H⋯O , O—H⋯N and C—H⋯O hydrogen bonds into a three-dimensional network.