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1.  (E)-Methyl 3-(4-ethyl­phen­yl)-2-{2-[(E)-(hy­droxy­imino)­meth­yl]phen­oxy­meth­yl}acrylate 
In the title compound, C20H21NO4, the two benzene rings are almost perpendicular to each other, making a dihedral angle of 86.1 (7)°. The hy­droxy­ethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane of the hy­droxy­ethanimine [C=N—OH] group being 0.011 (1) Å for the O atom. An intra­molecular C—H⋯O hydrogen bond occurs. The mol­ecules are linked into cyclic centrosymmetric R 2 2(6) dimers via O—H⋯N hydrogen bonds. Inter­molecular C—H⋯O hydrogen bonds link the mol­ecules, forming a C(8) chain along the a axis. The crystal packing is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S1600536811038359
PMCID: PMC3201344  PMID: 22058811
2.  (E)-2-({2-[(E)-(Hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-o-tolyl­acrylonitrile 
In the title compound, C18H16N2O2, the dihedral angle between the mean planes through the two benzene rings is 56.8 (6)°. The enoate group assumes an extended conformation. The hy­droxy­ethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being 0.047 (1) Å for the hy­droxy­imino O atom. In the crystal, the mol­ecules are linked into cyclic centrosymmetric dimers with R 2 2(6) motifs via O—H⋯N hydrogen bonds.
doi:10.1107/S1600536812001481
PMCID: PMC3275232  PMID: 22347088
3.  (E)-Methyl 2-({2-eth­oxy-6-[(E)-(hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-phenyl­acrylate 
In the title compound, C20H21NO5, the dihedral angle between the mean planes through the two rings is 47.1 (8)°. The enoate group assumes an extended conformation. The hy­droxy­ethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being 0.061 (1) Å for the O atom. In the crystal, mol­ecules are linked into cyclic centrosymmetric dimers with an R 2 2(6) motif via pairs of O—H⋯N hydrogen bonds. Inter­molecular C—H⋯O hydrogen bonds form a C(8) chain along the b axis. The crystal packing is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S1600536812014596
PMCID: PMC3344504  PMID: 22590266
4.  Methyl (E)-2-({2-[(E)-(hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-phenyl­acrylate 
In the title compound, C18H17NO4, the hy­droxy­ethanimine group is essentially coplanar with the ring to which it is attached [C—C—N—O torsion angle = 179.94 (14)°]. The mol­ecules are linked into cyclic centrosymmetric R 2 2(6) dimers via O—H⋯N hydrogen bonds and the crystal packing is further stabilized by C—H⋯O inter­actions.
doi:10.1107/S1600536812002711
PMCID: PMC3295410  PMID: 22412521
5.  (E)-2-({2-[(E)-(Hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-p-tolyl­acrylonitrile 
In the title compound, C18H16N2O2, the hy­droxy­ethanimine group is essentially coplanar with the ring to which it is attached (C—C—N—O torsion angle = −176.9°). Mol­ecules are linked into cyclic centrosymmetric R 2 2(6) dimers via O—H⋯N hydrogen bonds.
doi:10.1107/S160053681200270X
PMCID: PMC3297297  PMID: 22412487
6.  2-[2-(3-Chloro­phen­yl)-2-oxoeth­yl]-4-hy­droxy-3-(3-meth­oxy­benzo­yl)-2H-1λ6,2-benzothia­zine-1,1-dione 
In the title mol­ecule, C24H18ClNO6S, the heterocyclic thia­zine ring adopts a half chair conformation with the S and N atoms displaced by 0.318 (3) and 0.387 (3) Å, respectively, on the opposite sides from the mean plane formed by the remaining ring atoms. The benzene rings of the benzothia­zin unit and meth­oxy­benzoyl group are more or less coplanar, the dihedral angle between the mean planes of these rings being 12.37 (10)° while the chloro­phenyl ring is inclined at 81.87 (4) and 73.30 (5)°, respectively, to these rings. The mol­ecular structure is consolidated by intra­molecular O—H⋯O and C—H⋯N inter­actions and the crystal packing is stabilized by weak inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536812009014
PMCID: PMC3343952  PMID: 22590033
7.  Methyl (E)-2-({2-[(E)-(hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-(4-methyl­phen­yl)acrylate 
In the title compound, C19H19NO4, the dihedral angle between the mean planes through the benzene rings is 82.18 (7)°. The C=N double bond is trans-configured. The mol­ecules are linked into centrosymmetric dimers via pairs of O—H⋯N hydrogen bonds with the motif R 2 2(6). The crystal packing also features C—H⋯O inter­actions. The methyl group attached to one of the aromatic rings is disordered over two almost equally occupied positions [occpancy ratio = 0.51 (4):0.49 (4)].
doi:10.1107/S1600536812019046
PMCID: PMC3379223  PMID: 22719421
8.  1-(4-Chloro­phen­yl)-2-[4-hy­droxy-3-(3-meth­oxy­benzo­yl)-1,1-dioxo-2H-1λ6,2-benzothia­zin-2-yl]ethanone 
In the title mol­ecule, C24H18ClNO6S, the heterocyclic thia­zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.406 (5) and 0.444 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The meth­oxy­benzoyl and the chloro­phenyl rings lie roughly parallel to each other, with a dihedral angle between the mean planes of these rings of 8.86 (10)°. The mol­ecular structure is consolidated by intra­molecular O—H⋯O and C—H⋯O inter­actions and the crystal packing is stabilized by inter­molecular O—H⋯O and C—H⋯Cl hydrogen bonds.
doi:10.1107/S160053681201029X
PMCID: PMC3344017  PMID: 22589926
9.  (2,4-Dihy­droxy-6-meth­oxy­phen­yl)(3,5-dihy­droxy­phen­yl)methanone monohydrate 
The title benzophenone compound, C14H12O6·H2O, was isolated from the bark of Garcinia hombroniana Pierre (Guttiferae). The mol­ecule is twisted, the dihedral angle between the two benzene rings being 59.13 (7)°. The meth­oxy group is approximately coplanar with the attached benzene ring, with a C—O—C—C torsion angle of 1.91 (18)°. The water mol­ecule is disordered over two positions in a 0.555 (19):0.445 (19) ratio. An intra­molecular O—H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure is stabilized by inter­molecular O—H⋯O hydrogen bonds. These inter­actions link the mol­ecules into sheets parallel to the ac plane. The sheets are stacked along the b axis by π–π inter­actions, with centroid–centroid distances of 3.6219 (7) Å. A weak O—H⋯π inter­action was also noted.
doi:10.1107/S1600536811037913
PMCID: PMC3201278  PMID: 22065717
10.  Crystal structure of (2E)-1-(4-hy­droxy-3-meth­oxy­phen­yl)-3-(4-hy­droxy­phen­yl)prop-2-en-1-one 
In the title moleclue, C16H14O4, the dihedral angle between the benzene rings is 16.1 (3)°. The meth­oxy group is essentially coplanar with the benzene ring to which it is attached, with a C—O—C C torsion angle of 5.5 (9)°. In the crystal, mol­ecules are linked by O—H⋯O and bifurcated O—H⋯(O,O) hydrogen bonds, forming a three-dimensional network. The structure was refined as a two-component inversion twin.
doi:10.1107/S1600536814021953
PMCID: PMC4257319  PMID: 25484802
crystal structure; prop-2-en-1-one; chalcones; biological activity; hydrogen bonding
11.  2-(4-{4-[4-(Oxiran-2-ylmeth­oxy)phen­oxy]phen­yl}phen­oxy­meth­yl)oxirane 
In the title ep­oxy monomer, C24H22O5, the dihedral angle in the biphenyl residue is 3.34 (19)°, indicating a nearly coplanar conformation; this residue is not planar with the adjacent benzene ring [dihedral angle = 58.93 (14)°]. Each of the epoxide rings is disordered. Each epoxide ring was resolved over two alternative positions with site-occupancy ratios of 0.638 (10):0.362 (10) and 0.797 (9):0.203 (9).
doi:10.1107/S1600536812005740
PMCID: PMC3295490  PMID: 22412601
12.  Crystal structure of (E)-3-(2,4-di­meth­oxy­phen­yl)-1-(1-hy­droxy­naphthalen-2-yl)prop-2-en-1-one 
In the title compound, C21H18O4, the C=C bond of the central enone group adopts an E conformation. The dihedral angle formed by the benzene ring and the naphthalene ring system is 6.60 (2)°. The meth­oxy groups on the benzene ring are essentially coplanar with the ring; the C—C—O—C torsion angles being 1.6 (2) and −177.1 (1)°. The hy­droxy group attached to the naphthalene ring is involved in an intra­molecular O—H⋯O hydrogen bond. The relative conformation of the two double bonds in the enone group is s-cisoid. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into chains propagating along [010].
doi:10.1107/S1600536814018704
PMCID: PMC4186154  PMID: 25309211
crystal structure; chalcone; enone; benzochalcone; naphthalene
13.  5,7-Dihy­droxy-2-(3-hy­droxy-4,5-dimeth­oxy­phen­yl)-6-meth­oxy-4H-chromen-4-one 
The title compound, C18H16O8, was isolated from the plant Artemisia baldshuanica Krasch et Zarp. The mol­ecule is approximately planar, with the exception of the terminal methyl groups, the C atoms of which devitate from their attached ring planes by 1.243 (5) and 1.168 (5) Å. The dihedral angle between the substituted benzopyran and benzene rings is 5.8 (1)°; this near planarity could be due to conjugation or a packing effect. Intra­molecular O—H⋯O and C—H⋯O hydrogen bonds occur. In the crystal, mol­ecules are connected by O—H⋯O hydrogen bonds involving the hy­droxy and carbonyl groups, forming hydrogen-bonded chains along [001] and [1-10]. The chains are linked by C—H⋯O inter­actions.
doi:10.1107/S1600536813007381
PMCID: PMC3629625  PMID: 23634112
14.  2-(2-Hy­droxy-3-meth­oxy­phen­yl)-6H-perimidin-6-one 
The mol­ecule of the title perimidine derivative, C18H12N2O3, is essentially planar, the dihedral angle between the benzene and perimidine rings being 3.25 (5)°. The hy­droxy and meth­oxy groups lie in the plane of the benzene ring to which they are bound [O—C—C—C = 179.96 (11)° and C—O—C—C = −177.96 (12)°]. An intra­molecular O—H⋯N inter­action generates an S(6) ring motif. In the crystal, mol­ecules are linked by pairs of C—H⋯O inter­actions into dimers, which generate S(16) ring motifs. These dimers are arranged into sheets parallel to the ac plane and further stacked down the b axis by π–π inter­actions, with centroid–centroid distances in the range 3.5066 (8)–3.7241 (7) Å.
doi:10.1107/S1600536811006465
PMCID: PMC3051947  PMID: 21522458
15.  (E)-1-[2-Hy­droxy-4,6-bis­(meth­oxy­meth­oxy)phen­yl]-3-[3-meth­oxy-4-(meth­oxy­meth­oxy)phen­yl]prop-2-en-1-one 
The title compound, C22H26O9, crystallizes with two independent mol­ecules in the asymmetric unit in which the dihedral angles between the two benzene rings are 21.4 (2) and 5.1 (2)°. An intra­molecular O—H⋯O hydrogen bond occurs in each mol­ecule. Inter­molecular C—H⋯O hydrogen bonds stabilize the crystal structure.
doi:10.1107/S1600536811041213
PMCID: PMC3247344  PMID: 22219962
16.  Crystal structure of (E)-2-[(2-hy­droxy-4-meth­oxy­phen­yl)(phen­yl)methyl­idene]-N-phenyl­hydrazine-1-carboxamide 
The title compound, has an E conformation about the azomethine double bond and an intra­molecular O—H⋯N hydrogen bond involving the phenolic hydrogen and the azomethine N atom. In the crystal, mol­ecules are linked by bifurcated N—H⋯O hydrogen bonds involving the same acceptor atom, forming chains propagating along [001].
The title compound, C21H19N3O3, has an E conformation about the azomethine double bond. The central moiety of the hydrazinecarboxamide moiety [–N—N—C(=O)—N–] has an almost coplanar arrangement [maximum deviation for the C atom = 0.010 (2) Å]. This central moiety is flanked by three aromatic rings and its mean plane makes dihedral angles of 24.7 (1), 72.91 (12) and 34.26 (11) Å, respectively, with the phenolic ring, the phenyl ring attached to the same C atom as the phenolic ring, and the phenyl­hydrazine ring. The adjacent phenolic and phenyl rings are twisted away from each other to reduce steric hindrance and make a dihedral angle of 80.59 (12)°. The phenolic and phenyl­hydrazine rings are inclined to one another by 28.89 (11)°. The rigidity of the mol­ecule is increased by an intra­molecular O—H⋯N hydrogen bond involving the phenolic hydrogen and the azomethine N atom. In the crystal, the carbonyl O atom forms bifurcated hydrogen bonds with the two NH atoms of the hydrazinic group, leading to the formation of chains propagating along [001]. Within the chains there are also C—H⋯O hydrogen bonds present. The chains are linked via C=O⋯π [3.4316 (18) Å] and parallel slipped π–π inter­actions, involving inversion-related benzene rings [centroid–centroid distance = 3.8850 (14) Å; inter-planar distance = 3.3895 (10) Å; slippage = 1.899 Å], forming sheets lying parallel to (100).
doi:10.1107/S2056989015005757
PMCID: PMC4438824  PMID: 26029407
crystal structure; hydrazinecarboxamide; supra­molecular; hydrogen bonding; C=O⋯π inter­actions; π–π inter­actions
17.  9α-Hy­droxy-12-{[4-(4-meth­oxy­phen­yl)piperazin-1-yl]meth­yl}-4,8-dimethyl-3,14-dioxatricyclo­[9.3.0.02,4]tetra­dec-7-en-13-one 
The title compound, C26H36N2O5, was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methyl­ene-3,14-dioxatricyclo­[9.3.0.02,4]tetra­dec-7-en-13-one), wich was isolated from the chloro­form extract of the aerial parts of Anvillea radiata. The mol­ecule is built up from fused five- and ten-membered rings with the meth­oxy­phenyl­piperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring a flattened envelope conformation; the C(H)—C—C(H) atoms representing the flap lie out of the mean plane through the remaining four atoms by 0.343 (3) Å. The dihedral angle between the mean planes of the ten-membered ring and the lactone ring is 18.12 (14)°. An intra­molecular O—H⋯N hydrogen bond occurs. The crystal structure features weak C—H⋯O inter­actions.
doi:10.1107/S1600536812003662
PMCID: PMC3297315  PMID: 22412505
18.  1,1,2,2-Tetra­kis[2,4-dichloro-6-(dieth­oxy­meth­yl)phen­oxy­meth­yl]ethene 
In the title compound, C50H60Cl8O12, the mol­ecules are disordered about an inversion center located at the mid-point of the central C=C bond. These atoms show disorder and were modelled with two different orientations with site occupancies of 0.828 (3) and 0.172 (3). The dihedral angle between the two benzene rings in the asymmetric unit is 52.80 (6)°. Intramolecular C—H⋯O and C—H⋯Cl interactions occur and the crystal packing features inversion dimers linked by pairs of C—H⋯O bonds, generating R 2 2(10) loops.
doi:10.1107/S1600536812038299
PMCID: PMC3470353  PMID: 23125766
19.  2-[(2-Chloro­phen­yl)(hy­droxy)meth­yl]phenol 
In the title compound, C13H11ClO2, the dihedral angle between the mean planes of the 2-chloro­phenyl and phenol rings is 87.4 (9)°. The methyl hy­droxy group lies nearly perpendicular to the plane of its attached benzene ring [O—C—C—C torsion angle = 84.3 (3)°]. The two hy­droxy groups lie on the same side of the mol­ecule and are in a slightly twisted gauche conformation [O—C—C—O torsion angle = 77.1 (8)°] to each other. In the crystal, O—H⋯O hydrogen bonds between nearby methyl­hydroxy groups form dimers in alternating pairs aligned diagonally along the b axis. A view along the c axis reveals a hexa­meric aggregate mediated by a ring of six O—H⋯O hydrogen bonds generating an R 6 6(12) motif loop.
doi:10.1107/S1600536813018667
PMCID: PMC3793743  PMID: 24109330
20.  (2E)-1-(2-Hy­droxy-5-methyl­phen­yl)-3-(4-meth­oxy­phen­yl)prop-2-en-1-one 
In the title compound, C17H16O3, the dihedral angle between the aromatic rings is 4.59 (7)° and an intra­molecular O—H⋯O hydrogen bond generates an S(6) ring. In the crystal, adjacent mol­ecules are linked by C—H⋯O hydrogen bonds, leading to the formation of [001] supra­molecular chains. Weak C—H⋯π inter­actions consolidate the packing.
doi:10.1107/S1600536811015054
PMCID: PMC3089145  PMID: 21754540
21.  (E)-3-(4-Hy­droxy-3-meth­oxy­phen­yl)-1-(4-hy­droxy­phen­yl)prop-2-en-1-one 
In the title compound, C16H14O4, there is an intra­molecular O—H⋯O hydrogen bond. The benzene rings are inclined to one another by 13.89 (9)°. The prop-2-en-1-one group is twisted slightly, the O=C—Car—Car (ar = aromatic) and C=C—C=O torsion angles being −10.4 (3) and −7.4 (3)°, respectively. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, forming chains along [100]. These chains are further linked by O—H⋯O hydrogen bonds, forming corrugated sheets lying parallel to (010). There are C—H⋯π inter­actions present within the sheets.
doi:10.1107/S1600536814008757
PMCID: PMC4011235  PMID: 24860391
22.  (E)-3-(3-Chloro­phen­yl)-N-(4-hy­droxy-3-meth­oxy­benz­yl)acryl­amide 
In the title compound, C17H16ClNO3, the 4-hy­droxy-3-meth­oxy­benzyl group is planar [maximum atomic deviation = 0.0138 (16) Å] and is nearly perpendicular to the chloro­benzene ring, making a dihedral angle of 84.67 (4)°. The chloro­benzene and amide groups are located on the opposite sides of the C=C bond, showing an E configuration. The relatively long C=O bond distance of 1.2364 (19) Å and the short C—N bond distance of 1.341 (2) Å suggest electron delocalization in the amide fragment. Inter­molecular O—H⋯O, N—H⋯O and weak C—H⋯O hydrogen bonding is present in the crystal structure.
doi:10.1107/S1600536810022713
PMCID: PMC3006917  PMID: 21587920
23.  9-(4-Hy­droxy-3-meth­oxy­phen­yl)-3,3,6,6-tetra­methyl-3,4,5,6-tetra­hydro-9H-xanthene-1,8(2H,7H)-dione 
In the title compound, C24H28O5, the two cyclo­hexene rings adopt envelope conformations, and the planes through the coplanar atoms makes dihedral angles of 82.86 (6) and 77.90 (6)° with the benzene ring. The two cyclo­hexene rings make a dihedral angle of 5.33 (6)° between their least-squares planes. The pyran ring adopts a flattened boat conformation. In the crystal packing, mol­ecules are linked into two-dimensional networks parallel to the ab plane via O—H⋯O and C—H⋯O inter­actions.
doi:10.1107/S1600536810020258
PMCID: PMC3007007  PMID: 21587786
24.  2-[N-(4-{4-[(2-Hy­droxy-5-meth­oxy­benzyl­idene)amino]­benz­yl}phen­yl)carboximido­yl]-4-meth­oxy­phenol 
In the title Schiff base, C29H26N2O4, the complete molecule is generated by a crystallographic twofold axis and is V-shaped. The planes of the benzene rings of the central diphenyl­methane unit make a dihedral angle of 78.11 (4)° while adjacent benzene and 5-meth­oxy­salicyl­idene rings are twisted with respect to each other by a dihedral angle of 11.84 (8)°. The Schiff base is in the enol–imino form and an intra­molecular O—H⋯N hydrogen bond is observed.
doi:10.1107/S1600536812010550
PMCID: PMC3344086  PMID: 22606089
25.  (S)-Methyl 2-{(S)-2-[bis­(4-meth­oxy­phen­yl)methyl­idene­amino]-3-hy­droxy­propanamido}-3-methyl­butano­ate 
The title compound, C24H30N2O6, a Schiff base, adopts an extended conformation in which the meth­oxy groups are essentially coplanar with the aromatic ring to which they are bonded (mean planes fitted through the non-H atoms of each methoxyphenyl group have r.m.s. deviations of 0.078 and 0.044 Å) and the angle between mean planes fitted through the aromatic rings is 87.57 (10)°. An intra­molecular N—H⋯N hydrogen bond keeps the imine and amide groups essentially coplanar. A mean plane fitted through these groups has an r.m.s. deviation of 0.0545 Å. Additional O—H⋯O hydrogen bonding parallel with the a axis links the mol­ecules into a hydrogen-bonded chain in the crystal. C—H⋯O and C—H⋯π inter­actions are found within the crystal packing. The compound has been assigned the S,S configuration on the basis of the chemical synthesis, which used pure homotopic l-amino acids, and we have no reason to believe that the compound has epimerized.
doi:10.1107/S1600536810049032
PMCID: PMC3050411  PMID: 21522640

Results 1-25 (104655)