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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.  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
7.  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
8.  Crystal structures of methyl (E)-3-(2-chloro­phen­yl)-2-({2-[(E)-2-nitro­vin­yl]phen­oxy}meth­yl)acrylate and methyl (E)-2-({4-chloro-2-[(E)-2-nitro­vin­yl]phen­oxy}meth­yl)-3-(2-chloro­phen­yl)acrylate 
In the title compounds, (I) and (II), both of which crystallize in the monoclinic space group P21/n, the methyl acrylate and nitro­vinyl units are relatively planar with an E conformation about the C=C bonds. The two aromatic rings are inclined to one another by 74.87 (9) and 75.65 (2)° for compounds (I) and (II), respectively. In the crystal of (I), chains along the b axis are formed via C—H⋯O hydrogen bonds. In the crystal of (II), mol­ecules are linked by C—H⋯O hydrogen bonds, forming sheets parallel to the ac plane.
The title compounds, C19H16ClNO5, (I), and C19H15Cl2NO5, (II), both crystallize in the monoclinic space group P21/n. They differ essentially in the orientation of the methyl acetate group, with the C=O bond directed towards the NO2 group in (I) but away from it in (II). In compound (I), the mean plane of the methyl acrylate unit is planar, with a maximum deviation of 0.0044 (2) Å for the methyl C atom, while in (II) this deviation is 0.0147 Å. The inter­planar angles between the two aromatic rings are 74.87 (9) and 75.65 (2)° for compounds (I) and (II), respectively. In both compounds, the methyl acrylate and nitro­vinyl groups each adopt an E conformation about the C=C bond. In the crystal of (I), mol­ecules are linked by C—H⋯O hydrogen bonds forming chains along the b axis. The chains are linked via C—H⋯Cl hydrogen bonds, forming sheets parallel to the ab plane. The sheets are linked via C—H⋯π inter­actions, forming a three-dimensional structure. In the crystal of (II), mol­ecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(30) ring motif. The dimers are linked via C—H⋯O hydrogen bonds, forming sheets parallel to the ac plane and enclosing R 4 4(28) ring motifs. The sheets are linked via parallel slipped π–π inter­actions (inter­centroid distances are both ca 3.86 Å), forming a three-dimensional structure.
doi:10.1107/S2056989016001493
PMCID: PMC4770962  PMID: 26958402
crystal structure; 2-cyano­acrylates; phenyl acrylates; cinnamic acid derivatives; C—H⋯O hydrogen bonding
9.  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
10.  2-[1-({2-[1-(2-Hy­droxy-5-{[meth­yl(phen­yl)amino]­meth­yl}phen­yl)ethyl­idene­amino]­eth­yl}imino)­eth­yl]-4-{[meth­yl(phen­yl)amino]­meth­yl}phenol 
Mol­ecules of the title compound, C34H38N4O2, lie across crystallographic inversion centres. The crystal packing can be described by alternating zigzag chains along the c axis in which the molecules are linked by van der Waals interactions. There is an intra­molecular O—H⋯N hydrogen bond and the two benzene rings in the asymmetric unit make a dihedral angle of 79.81 (6)°.
doi:10.1107/S1600536812017904
PMCID: PMC3344659  PMID: 22590421
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.  2,4-Di­bromo-6-{[(5-chloro-2-methyl­phen­yl)imino]­meth­yl}phenol 
In the mol­ecular structure of the title Schiff base, C14H10Br2ClNO, the chloro­phenyl ring and di­bromo­phenol ring are almost coplanar; the dihedral angle between the planes of the two rings is 10.50 (18)°. There is an intra­molecular O—H⋯N hydrogen bond, with an O⋯N distance of 2.576 (4)Å. The crystal structure is stabilized by π–π stacking of neighbouring aromatic rings along the b-axis direction [centroid–centroid distance = 3.6896 (5) Å].
doi:10.1107/S1600536813017558
PMCID: PMC3770443  PMID: 24046728
13.  (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
14.  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
15.  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
16.  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
17.  2-((E)-{[4-(Hy­droxy­meth­yl)phen­yl]imino}­meth­yl)phenol 
The title compound, C14H13NO2, adopts the enol–imine tautomeric form, with an intra­molecular O—H⋯N hydrogen bond which generates an S(6) ring motif. The dihedral angle between the aromatic rings is 7.85 (7)°. The crystal structure is stabilized by O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds, forming a two-dimensional array that stacks along the a axis. In addition, a C—H⋯π inter­action contributes to the stabilization of the crystal packing.
doi:10.1107/S1600536812019368
PMCID: PMC3379224  PMID: 22719422
18.  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
19.  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
20.  (E)-2-({2-[(E)-(Hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-phenyl­acrylonitrile 
In the title compound, C17H14N2O2, the hy­droxy­ethanimine group adopts an anti­periplanar conformation. In the crystal, mol­ecules are linked by O—H⋯N hydrogen bonds, forming zigzag chains running along the c axis.
doi:10.1107/S1600536812003923
PMCID: PMC3297320  PMID: 22412510
21.  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
22.  2-{(1E)-1-[(3-{(E)-[1-(2-Hy­droxy-4-meth­oxy­phen­yl)ethyl­idene]amino}-2,2-di­methyl­prop­yl)imino]­eth­yl}-5-meth­oxy­phenol 
Mol­ecules of the title compound, C23H30N2O4, are located on a crystallographic mirror plane. The mol­ecule has a curved shape with the dihedral angle formed between the two benzene rings being 55.26 (5)°. Intra­molecular O—H⋯N hydrogen bonds are noted. In the crystal, supra­molecular layers are formed in the ac plane owing to the presence of C—H⋯π inter­actions.
doi:10.1107/S1600536811038815
PMCID: PMC3201500  PMID: 22058812
23.  1-[(4-Chloro­phen­yl)(phenyl­imino)­meth­yl]-7-meth­oxy-2-naphthol–1,4-diaza­bicyclo­[2.2.2]octane (2/1) 
In the crystal structure of the title cocrystal, 2C24H18ClNO2·C6H12N2, the 1,4-diaza­bicyclo­[2.2.2]octane mol­ecule is located on a twofold rotation axis and linked to the two triaryl­imine mol­ecules by O—H⋯N hydrogen bonds, forming a 2:1 aggregate. C—H⋯Cl inter­actions are also observed. In the triaryl­imine mol­ecule, the naphthalene ring system makes dihedral angles of 80.39 (6) and 82.35 (6)°, respectively, with the phenyl and benzene rings. The dihedral angle between these two latter rings is 87.09 (7)°.
doi:10.1107/S1600536810034690
PMCID: PMC2983128  PMID: 21587495
24.  (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
25.  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

Results 1-25 (114929)