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1.  (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
2.  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
3.  (E)-Methyl 3-(4-chloro­phen­yl)-2-{2-[(E)-(hy­droxy­imino)­meth­yl]phen­oxy­meth­yl}acrylate 
In the title compound, C18H16ClNO4, the dihedral angle between the mean planes through the aromatic rings is 83.8 (8)°. The hy­droxy­ethanimine group is essentially coplanar with the ring to which it is attached [O—N—C—C torsion angle = −177.96 (13)°]. The mol­ecules are linked into centrosymmetric R 2 2(6) dimers via O—H⋯N hydrogen bonds. The crystal packing is further stabilized by C—H⋯O inter­actions.
doi:10.1107/S1600536811038372
PMCID: PMC3201559  PMID: 22064839
4.  (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
5.  (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
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.  (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
8.  4-Bromo-2-({4-[(hy­droxy­imino)­meth­yl]phen­yl}imino­meth­yl)phenol 
In the title compound, C14H11BrN2O2, the mean planes of the two benzene rings are almost parallel to each other, making a dihedral angle of 4.09 (1)°. An intra­molecular O—H⋯N hydrogen bond occurs. In the crystal, inter­molecular O—H⋯N and C—H⋯O hydrogen bonds link the mol­ecules into a chain-like supra­molecular structure.
doi:10.1107/S160053681002698X
PMCID: PMC3007216  PMID: 21588325
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.  4-Chloro-2-((E)-{3-[1-(hydroxy­imino)eth­yl]phen­yl}imino­meth­yl)phenol 
The title compound, C15H13ClN2O2, adopts an E conformation with respect to the azomethine C=N bond. The aniline and phenol rings are almost coplanar, making a dihedral angle of 3.33 (2)°. In the crystal, the mol­ecules lie about inversion centers, forming dimers that are connected by inter­molecular O—H⋯N hydrogen bonds, resulting in six-membered rings with graph-set motif R 2 2(6). In addition, there is a strong inter­molecular O—H⋯N hydrogen-bonding inter­action, resulting in an S(6) ring motif. Weak π–π inter­actions between the benzene rings [centroid–centroid distance = 3.809 (1) Å] further stabilize the crystal structure.
doi:10.1107/S1600536809045942
PMCID: PMC2972112  PMID: 21578758
11.  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
12.  (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
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.  14-Hy­droxy-11-[(E)-4-meth­oxy­benzyl­idene]-8-(4-meth­oxy­phen­yl)-5-thia-3,13-diaza­hepta­cyclo­[13.7.1.19,13.02,9.02,14.03,7.019,23]tetra­cosa-1(22),15(23),16,18,20-pentaen-10-one 
In the title compound, C36H32N2O4S, the piperidine ring adopts a chair conformation, while the five-membered pyrrolidine (with a C atom as the flap atom) and thia­zolidine (with the S atom as the flap atom) rings adopt envelope conformations. The naphthalene ring system makes dihedral angles of 18.82 (5) and 40.92 (5)° with the two meth­oxy-substituted benzene rings. In the crystal, centrosymmetrically-related mol­ecules are linked into dimers via pairs of C—H⋯O and C—H⋯N hydrogen bonds. An intra­molecular O—H⋯N hydrogen bond is also observed. The crystal structure is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S160053681104061X
PMCID: PMC3247613  PMID: 22219918
15.  Methyl 11-hy­droxy-9-[1-(4-meth­oxy­phen­yl)-4-oxo-3-phen­oxy­azetidin-2-yl]-18-oxo-10-oxa-2-aza­penta­cyclo­[9.7.0.01,8.02,6.012,17]octa­deca-12(17),13,15-triene-8-carboxyl­ate 
In the title compound, C34H32N2O8, one of the pyrrolidine rings in the pyrrolizidine ring system adopts a twist conformation, whereas the other ring adopts an envelope conformation (C atom as flap). The five-membered ring in the indene ring system and the fused furan ring also adopt envelope conformations (C and O atoms as flaps, respectively). The β-lactam ring makes dihedral angles of 23.41 (2) and 25.98 (2)°, respectively, with the attached meth­oxy­phenyl and phen­oxy rings. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond, generating an S(5) motif. In the crystal, mol­ecules are linked into C(12) chains running along the a axis by C—H⋯O hydrogen bonds. The structure is further consolidated by weak inter­molecular C—H⋯π and π–π inter­actions [centroid–centroid distance = 3.7987 (14) Å].
doi:10.1107/S1600536812027341
PMCID: PMC3393998  PMID: 22798863
16.  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
17.  (E)-4-Meth­oxy-2-(o-tolyl­imino­meth­yl)phenol 
In the mol­ecule of the title compound, C15H15NO2, the aromatic rings are oriented at a dihedral angle of 15.46 (6)°. An intra­molecular O—H⋯N hydrogen bond results in the formation of a nearly planar six-membered ring [maximum deviation of 0.035 (5) Å for the N atom] which is almost coplanar with the adjacent ring, making a dihedral angle of 0.8 (3)°. The title organic mol­ecule is a phenol–imine tautomer, as evidenced by the C—O, C—N and C—C bond lengths. Mol­ecules are linked by inter­molecular C—H⋯O hydrogen bonds that generate a C(5) chain. C—H⋯π and π–π inter­actions exist in the structure. The π–π inter­action occurs between the phenol ring and its symmetry equivalent at (1 − x, 1 − y, −z), with a centroid–centroid distance of 3.727 (7) Å and a plane-to-plane separation of 3.383 (5) Å, resulting in an offset angle of 24.82 (1)°.
doi:10.1107/S1600536809009192
PMCID: PMC2968945  PMID: 21582515
18.  2-[(E)-Meth­oxy­imino]-2-{2-[(2-methyl­phen­oxy)meth­yl]phen­yl}ethanoic acid 
In the title compound, C17H17NO4, the dihedral angle between the two aromatic rings is 59.64 (5)°. The (meth­oxy­imino)­ethanoic acid fragment is nearly perpendicular to the attached benzene ring [dihedral angle = 81.07 (4)°]. In the crystal, pairs of O—H⋯O hydrogen bonds between carb­oxy groups link mol­ecules into inversion dimers. In addition, π–π stacking inter­actions between inversion-related benzene rings are observed [centroid–centroid distance = 3.702 (1) Å].
doi:10.1107/S1600536812030711
PMCID: PMC3414343  PMID: 22904876
19.  (E)-1-{4-[Bis(4-meth­oxy­phen­yl)meth­yl]piperazin-1-yl}-3-(4-eth­oxy-3-meth­oxy­phen­yl)prop-2-en-1-one 
In the mol­ecule of the title compound, C31H36N2O5, the piperazine ring displays a chair conformation. The dihedral angle between the benzene rings of the bis­(4-meth­oxy­phen­yl)methyl group is 83.42 (15)°. In the crystal, centrosymmetric­ally related mol­ecules are linked through pairs of C—H⋯O hydrogen bonds into dimers, generating an R 2 2(10) ring motif. The dimers are further connected into chains parallel to [2-10] by C—H⋯O hydrogen bonds involving the meth­oxy groups.
doi:10.1107/S1600536812012767
PMCID: PMC3344185  PMID: 22606188
20.  Di-tert-butyl (2R,3R)-2-{[(2E)-3-(4-acet­yloxy-3-meth­oxy­phen­yl)prop-2-eno­yl]­oxy}-3-hy­droxy­butane­dioate 
In the title mol­ecule, C24H32O10, one tert-butyl ester group is folded towards the central benzene ring while the other is directed away. The acetyl group is almost perpendicular to the benzene ring to which it is connected [C—C—O—C torsion angle = 90.4 (12)°]. The conformation about the ethene bond [1.313 (7) Å] is E. The atoms of the benzene ring and its attached ester group and part of the hy­droxy tert-butyl ester side chain are disordered over two sets of sites in a 50:50 ratio. Linear supra­molecular chains along the a axis mediated by hy­droxy–carbonyl O—H⋯O hydrogen bonds feature in the crystal packing. The same H atom also partakes in an intra­molecular O—H⋯O inter­action.
doi:10.1107/S1600536812002784
PMCID: PMC3297296  PMID: 22412486
21.  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
22.  (2-Hy­droxy-7-meth­oxy­naphthalen-1-yl)(phen­yl)methanone 
In the mol­ecule of the title compound, C18H14O3, there is an intra­molecular O—H⋯O=C hydrogen bond between the carbonyl and hy­droxy groups on the naphthalene ring system. The angles between the C=O bond vector and the least-squares planes of the naphthalene ring system and the phenyl ring are 30.58 (6) and 42.82 (7)°, respectively, while the dihedral angle between the naphthalene ring system and the phenyl ring is 58.65 (5)°. In the crystal, mol­ecules are connected by pairs of inter­molecular O—H⋯O=C hydrogen bonds, forming centrosymmetric dimers.
doi:10.1107/S1600536810038547
PMCID: PMC2983170  PMID: 21587645
23.  (E)-3-(8-Benz­yloxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1-[2-hy­droxy-4,6-bis­(meth­oxy­meth­oxy)phen­yl]prop-2-en-1-one 
In the title mol­ecule, C28H28O9, the phenol and the benzene rings adjacent to the α,β-unsaturated ketone unit are inclined at 9.15 (13)° to each other. The terminal phenyl ring is oriented with respect to the phenol ring at a dihedral angle of 85.88 (13)°. In the crystal, the methyl­ene C atoms of the dihydro­dioxine ring are disordered over two sites with an occupancy ratio of 0.463 (18):0.537 (18), and both disordered components of the dihydro­dioxine ring adopt twisted-chair conformations. An intra­molecular O—H⋯O hydrogen bond and weak inter­molecular C—H⋯O hydrogen bonds are present in the crystal structure.
doi:10.1107/S160053681100924X
PMCID: PMC3100013  PMID: 21754185
24.  (2-Hy­droxy-7-meth­oxy­naphthalen-1-yl)(4-methyl­phen­yl)methanone 
In the title compound, C19H16O3, an intra­molecular O—H⋯O=C hydrogen bond is formed between the hy­droxy and carbonyl groups on the naphthalene ring system, resulting in an S(6) ring. The angles between the C=O bond vector and the least-squares planes of the naphthalene ring system and the benzene ring are 27.63 (6) and 47.99 (7)°, respectively. The dihedral angle between the latter planes is 61.39 (5)°. In the crystal, two mol­ecules are connected by pairs of inter­molecular O—H⋯O=C hydrogen bonds, forming centrosymmetric dimers with an R 2 2(4) graph-set motif. The mol­ecular packing features C—H⋯π interactions.
doi:10.1107/S1600536810040614
PMCID: PMC3009359  PMID: 21589009
25.  Bis{2,6-bis­[(2-hy­droxy-5-methyl­phen­yl)imino­meth­yl]pyridine} monohydrate 
The title compound, 2C21H19N3O2·H2O, was synthesized by a Schiff base condensation of 2,6-diformyl­pyridine with 2-amino-4-methyl­phenol in ethanol. In the crystal, two mol­ecules of 2,6-bis­[(2-hy­droxy-5-methyl­phen­yl)imino­meth­yl]pyridine dimer­ize via hydrogen bonding to a water mol­ecule, which lies on a twofold axis. There are also intra­molecular phenol–imine hydrogen bonds. The dimers are further linked via π–π (phen­yl–pyridine) [centroid–centroid distance = 3.707 (2) Å] and π–π edge-to-edge [3.392 (2) Å] inter­actions. The dihedral angles between the central ring and the two pendant rings are 11.46 (8) and 2.06 (8)° while the pendant rings make a dihedral angle of 10.14 (8)°.
doi:10.1107/S1600536811045399
PMCID: PMC3238860  PMID: 22199713

Results 1-25 (92048)