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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 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 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
5.  (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
6.  4-[(E)-(2,4-Difluoro­phen­yl)(hydroxy­imino)meth­yl]piperidinium picrate 
The title compound, C12H15F2N2O+·C6H2N3O7 −, a picrate salt of 4-[(E)-(2,4-difluoro­phen­yl)(hydroxy­imino)meth­yl]piper­idine, crystallizes with two independent mol­ecules in a cation–anion pair in the asymmetric unit. In the cation, a methyl group is tris­ubstituted by hydroxy­imino, piperidin-4-yl and 2,4-difluoro­phenyl groups, the latter of which contains an F atom disordered over two positions in the ring [occupancy ratio 0.631 (4):0.369 (4)]. The mean plane of the hydr­oxy group is in a synclinical conformation nearly orthogonal [N—C—C—C = 72.44 (19)°] to the mean plane of the piperidine ring, which adopts a slightly distorted chair conformation. The dihedral angle between the mean plane of the 2,4-difluoro­phenyl and piperidin-4-yl groups is 60.2 (3)°. In the picrate anion, the mean planes of the two o-NO2 and single p-NO2 groups adopt twist angles of 5.7 (2), 25.3 (7) and 8.3 (6)°, respectively, with the attached planar benzene ring. The dihedral angle between the mean planes of the benzene ring in the picrate anion and those in the hydroxy­imino, piperidin-4-yl and 2,4-difluoro­phenyl groups in the cation are 84.9 (7), 78.9 (4) and 65.1 (1)°, respectively. Extensive hydrogen-bond inter­actions occur between the cation–anion pair, which help to establish the crystal packing in the unit cell. This includes dual three-center hydrogen bonds with the piperidin-4-yl group, the phenolate and o-NO2 O atoms of the picrate anion at different positions in the unit cell, which form separate N—H⋯(O,O) bifurcated inter­molecular hydrogen-bond inter­actions. Also, the hydr­oxy group forms a separate hydrogen bond with a nearby piperidin-4-yl N atom, thus providing two groups of hydrogen bonds, which form an infinite two-dimensional network along (011).
doi:10.1107/S1600536809035363
PMCID: PMC2970333  PMID: 21577832
7.  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
8.  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
9.  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
10.  (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
11.  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
12.  4-{2-Meth­oxy-6-[(4-methyl­phen­yl)imino­meth­yl]phen­oxy}phthalonitrile 
In the mol­ecule of the title compound, C23H17N3O2, the methoxy­phenyl ring is oriented at dihedral angles of 13.34 (12) and 88.83 (12)° with respect to the methyl­phenyl and phthalonitrile rings, respectively; the dihedral angle between methyl­phenyl and phthalonitrile rings is 89.67 (10)°. In the crystal structure, weak inter­molecular C—H⋯N inter­actions link mol­ecules into chains. A weak C—H⋯π inter­action is also found..
doi:10.1107/S1600536809015402
PMCID: PMC2977837  PMID: 21583974
13.  (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
14.  1-{(E)-[3-(1H-Imidazol-1-yl)-1-(4-meth­oxy­phen­yl)propyl­idene]amino}-3-(2-methyl­phen­yl)urea 
In the title compound, C21H23N5O2, the conformation about the imine bond [1.287 (3) Å] is E. Overall, the mol­ecule has a disk shape, the dihedral angles between the imidazole ring and the meth­oxy­phenyl and methyl­phenyl rings being 49.42 (13) and 42.62 (13)°, respectively; the dihedral angle between the benzene rings is 20.11 (11)°. In the urea moiety, the N—H atoms are anti to each other and one of these forms an intra­molecular N—H⋯N hydrogen bond. In the crystal, centrosymmetric dimers are formed via N—H⋯N(imidazole) hydrogen bonds, which are connected into a three-dimensional architecture by C—H⋯O(carbon­yl) and (methyl­ene)C—H⋯π inter­actions. The crystal studied was a non-merohedral twin with a minor component of 48.3 (1)%.
doi:10.1107/S1600536812021903
PMCID: PMC3379375  PMID: 22719573
15.  5-((Meth­oxy­imino)­{2-[(2-methyl­phen­oxy)meth­yl]phen­yl}meth­yl)-N-phenyl-1,3,4-oxa­diazol-2-amine 
In the title mol­ecule, C24H22N4O3, the plane of the oxa­diazole ring forms a dihedral angle of 32.41 (12)° with that of the phenyl ring and dihedral angles of 74.51 (10) and 56.38 (10)° with the planes of the benzene rings. In the crystal, pairs of N—H⋯N hydrogen bonds link molecules into inversion dimers featuring R 2 2(8) graph-set motifs.
doi:10.1107/S1600536814003821
PMCID: PMC3998470  PMID: 24765044
16.  3-(2-Chloro-3-hy­droxy-4-meth­oxy­phen­yl)-1-(4,5-dimeth­oxy-2-methyl­phen­yl)prop-2-en-1-one 
The title compound, C19H19ClO5, is a chloro derivative of a biologically significant chalcone family. The mean plane of the two substituted benzene rings are twisted by 55.33 (8)° with respect to each other. An intra­molecular C—H⋯Cl hydrogen bond generates an S(5) graph-set motif. In the crystal, a bifurcated O—H⋯(O,O) hydrogen bond leads to an R 1 2(5) graph-set motif and to the formation of zigzag chains propagating along the c-axis direction. A weak π–π inter­action involving the methyl­phenyl rings [centroid–centroid distance = 3.8185 (10) Å] and C—H⋯π inter­actions also occur.
doi:10.1107/S1600536812038275
PMCID: PMC3470302  PMID: 23125715
17.  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
18.  2-{(E)-[(3-Iodo-4-methyl­phen­yl)imino]­meth­yl}-4-(trifluoro­meth­oxy)phenol 
The title compound, C15H11F3INO2, adopts the enol–imine tautomeric form. The mol­ecule displays an E conformation with respect to the imine C=N double bond. The dihedral angle between the two benzene rings is 12.4 (2)°. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond, which generates an S(6) ring motif. The trifluoro­meth­oxy­phenyl group is disordered over two sites with an occupancy ratio of 0.621 (6):0.379 (6). The crystal structure features C—H⋯π inter­actions.
doi:10.1107/S1600536812026876
PMCID: PMC3393956  PMID: 22798821
19.  Crystal structure of (2Z,5Z)-3-(4-meth­oxy­phen­yl)-2-[(4-meth­oxy­phenyl)­imino]-5-[(E)-3-(2-nitro­phen­yl)allyl­idene]-1,3-thia­zolidin-4-one 
The thia­zole ring of the title compound is twisted with respect to the three benzene rings, making dihedral angles of 25.52 (12), 85.77 (12) and 81.85 (13)°.
In the title compound, C26H21N3O5S, the thia­zole ring is nearly planar with a maximum deviation of 0.017 (2) Å, and is twisted with respect to the three benzene rings, making dihedral angles of 25.52 (12), 85.77 (12) and 81.85 (13)°. In the crystal, weak C—H⋯O hydrogen bonds and C—H⋯π inter­actions link the mol­ecules into a three-dimensional supra­molecular architecture. Aromatic π–π stacking is also observed between the parallel nitro­benzene rings of neighbouring mol­ecules, the centroid-to-centroid distance being 3.5872 (15) Å.
doi:10.1107/S2056989016000207
PMCID: PMC4770957  PMID: 26958377
crystal structure; thia­zolidinone; hydrogen bonding; π–π stacking
20.  Crystal structure of (2E)-1-(4-hy­droxy-1-methyl-2-oxo-1,2-di­hydro­quinolin-3-yl)-3-(4-hy­droxy-3-meth­oxy­phen­yl)prop-2-en-1-one 
The crystal packing of the title compound features O—H⋯O hydrogen bonds, which form one-dimensional chains of mol­ecules further linked via π–π inter­actions.
In the title compound, C20H17NO5, the dihedral angle between the mean plane of the di­hydro­quinoline ring system (r.m.s. deviation = 0.003 Å) and the benzene ring is 1.83 (11)°. The almost planar conformation is a consequence of an intra­molecular O—H⋯O hydrogen bond and the E configuration about the central C=C bond. In the crystal structure, O—H⋯O hydrogen bonds generate chains of mol­ecules along the [10-1] direction. These chains are linked via π–π inter­actions [inter-centroid distances are in the range 3.6410 (16)–3.8663 (17) Å].
doi:10.1107/S2056989015005630
PMCID: PMC4438805  PMID: 26029406
crystal structure; 4-hy­droxy-1,2-di­hydro­quinolin-2(1H)-one; α,β-unsaturated ketones; hydrogen bonding; π–π inter­actions
21.  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
22.  2-{(E)-[(4-Methyl­phen­yl)imino]­meth­yl}-4-nitro­phenol–2-{(E)-[(4-methyl­phen­yl)iminio]meth­yl}-4-nitro­phenolate (0.60/0.40) 
The crystal of the title compound, 0.6C14H12N2O3·0.4C14H12N2O3, contains a mixture of its neutral (OH containing) and zwitterionic (NH containing) forms, in a 0.60 (4):0.40 (4) ratio. The former generates an S(6) loop via an intra­molecular O—H⋯N hydrogen bond and the latter generates an S(6) loop via an N—H⋯O hydro­gren bond. The aromatic rings are oriented at a dihedral angle of 42.52 (10)°. In the crystal, C—H⋯π inter­actions occur and aromatic π–π stacking inter­actions [centroid–centroid separations = 3.7106 (12) and 3.9177 (13) Å] consolidate the packing.
doi:10.1107/S1600536811032028
PMCID: PMC3200654  PMID: 22058946
23.  4-[(E)-(3-Chloro-4-methyl­phen­yl)imino­meth­yl]-2-methoxy-3-nitro­phenyl acetate 
The title compound, C17H15ClN2O5, displays a trans-configuration with respect to the C=N double bond. The mol­ecule is twisted, the dihedral angle between the mean planes of the two benzene rings being 18.70 (12)°. The nitro, meth­oxy and acetyl groups are oriented at 80.70 (11), 35.2 (2) and 72.35 (10)°, respectively, to the benzene ring to which they are bonded. The crystal structure is stabilized by weak C—H⋯O hydrogen-bonding contacts.
doi:10.1107/S1600536811055590
PMCID: PMC3274996  PMID: 22346941
24.  (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
25.  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

Results 1-25 (145498)