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author:("dudek, Michal")
1.  2,2′-{[2-(2-Hy­droxy­phen­yl)-4-methyl­imidazolidine-1,3-di­yl]bis­(methyl­ene)}diphenol 
The asymmetric unit in the title compound, C24H26N2O3, comprises two independent mol­ecules (A and B). In molecule A, the central 2-hydroxyphenyl ring is inclined to the mean plane of the major component of the imidazolidine ring by 84.52 (14)°, and by 68.08 (9) and 47.48 (9)° to the outer phenol rings. The later are inclined to one another by 66.76 (9)° and by 78.12 (14) and 80.20 (14)° to the imidazoline ring mean plane. In molecule B, the central 2-hydroxyphenyl ring is inclined to the mean plane of the imidazolidine ring by 73.64 (10)°, and by 75.60 (8) and 38.32 (9)° to the outer phenol rings. The later are inclined to one another by 69.47 (9)° and by 82.60 (10) and 64.26 (10)° to the imidazolidine ring mean plane. In each of the independent mol­ecules, two intra­molecular O—H⋯N hydrogen bond form S(6) ring motifs. In disordered mol­ecule A, the O—H groups of the 2-hy­droxy­benzyl groups are also involved in intra­molecular O—H⋯O hydrogen bonds, with the O atom of the hy­droxy­phenyl group acting as the acceptor. In the crystal, A molecules are linked by pairs of O—H⋯O hydrogen bonds forming inversion dimers. These dimers are linked to the B molecules via O—H⋯O hydrogen bonds forming double-layered slabs lying parallel to the bc plane.
doi:10.1107/S1600536813019417
PMCID: PMC3793786  PMID: 24109373
2.  2,2′-{[2-(2-Chloro­phen­yl)-4-methyl­imidazolidine-1,3-di­yl]bis­(methyl­ene)}diphenol 
In the title compound, C24H25ClN2O2, the 2-hy­droxy­benzyl substituents and the 2-chloro­phenyl group occupy the sterically preferred equatorial positions, whereas the methyl group occupies the axial position. The imidazolidine ring adopts an envelope conformation with one of the N atoms adjacent to the methylene group as the flap. The chloro­phenyl substit­uent approaches a nearly perpendicular orientation relative to the mean plane of the imidazolidine ring, making a dihedral angle of 73.44 (12)° and the Cl atom is almost coplanar with the C atom bearing the chloro­phenyl substituent [Cl—C—C—C torsion angle = 1.1 (3)°]. The hy­droxy­benzyl groups make dihedral angles of 71.23 (15) and 69.13 (19)° with the mean plane of the heterocyclic ring. The dihedral angle between the two hy­droxy­benzyl groups is 69.61 (12)°. The mol­ecular structure features two intra­molecular O—H⋯N hydrogen bonds with graph-set motif S(6) between the phenolic hydroxyl groups and N atoms.
doi:10.1107/S1600536813017923
PMCID: PMC3793727  PMID: 24109314
3.  2,2′-[(4-Methyl-2-phenyl­imidazolidine-1,3-di­yl)bis­(methyl­ene)]diphenol 
The methyl-substituted imidazolidine ring of the title compound, C24H26N2O2, adopts an envelope conformation with the N atom adjacent to the methyl­ene group as the flap. The meth­yl–ethyl­ene fragment in this ring is disordered over two positions with an occupancy ratio of 0.899 (4):0.101 (4). The hy­droxy­benzyl groups are inclined at 71.57 (15) and 69.97 (19)° to the mean plane of major disorder component of the heterocyclic ring with an inter­planar angle between the two hy­droxy­benzyl groups of 66.00 (5)°. The phenyl substit­uent approaches a nearly perpendicular orientation relative to the mean plane of the imidazolidine ring, making a dihedral angle of 75.60 (12)°. This conformation is stabilized by two intra­molecular O—H⋯N bonds, which generate S(6) ring motifs.
doi:10.1107/S1600536813017893
PMCID: PMC3793710  PMID: 24109297
4.  Single-step synthesis of a new series of meso di-Mannich bases from the cyclic aminal (2S,7R,11S,16R)-1,8,10,17-tetraazapentacyclo[8.8.1.1.8,170.2,7011,16]icosane and p-substituted phenols 
Background
The results presented herein show that the cyclic aminal (2S,7R,11S,16R)-1,8,10,17-tetraazapentacyclo[8.8.1.1.8,170.2,7011,16]icosane (6), derived from cis-(meso)-1,2-diaminocyclohexane and formaldehyde, is a suitable substrate for the preption of a series of cis-meso Mannich bases such as 8a-l by reaction with p-substituted phenols 7a-l in basic media. These compounds are valuable synthetic products and may find application in asymmetric catalysis.
Results
The products were characterized principally by NMR and IR spectroscopy. Both the benzylic and aminalic protons of the perhydrobenzimidazolidine moiety were diastereotopic due to the presence of stereogenic nitrogen centers. The occurrence of intramolecular hydrogen bonding interactions was confirmed by the broad OH stretching vibration band in the IR spectra. Vibrational spectra were calculated using B3LYP at 6-31G(d,p) level, and the calculated frequencies for the νOH vibrations were compared to those of the experimental spectra. Hydrogen bonding interactions in the solid state were observed through the X-ray crystallography of 8j. Additionally, Mulliken charges and Fukui indices for 6 were calculated as theoretical descriptors of electrophilicity.
Conclusion
A new series of meso Mannich bases called 4,4′-disubstituted-2,2′-{[(3aR,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3-benzimidazole-1,3-diyl]bis(methylene)} diphenols (8a-l) which are derived from cis-(meso)-1,2-diaminocyclohexane, were obtained from cyclic aminal 6. These results confirmed the behavior of 6 as an electrophilic preformed reagent in Mannich reactions in basic media.
doi:10.1186/1752-153X-7-100
PMCID: PMC3698105  PMID: 23758899
5.  meso-4,4′-Dimeth­oxy-2,2′-{[(3aR,7aS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-benz­imidazole-1,3-di­yl]bis­(methyl­ene)}diphenol 
The title compound, C23H30N2O4, a di-Mannich base derived from 4-meth­oxy­phenol and cis-1,2-di­amine­cyclo­hexane, has a perhydro­benzimidazolidine nucleus, in which the cyclo­hexane ring adopts a chair conformation and the heterocyclic ring has a half-chair conformation with a C—N—C—C torsion angles of −48.14 (15) and −14.57 (16)°. The mean plane of the heterocycle makes dihedral angles of 86.29 (6) and 78.92 (6)° with the pendant benzene rings. The mol­ecular structure of the title compound shows the presence of two inter­actions between the N atoms of the imidazolidine ring and the hydroxyl groups through intra­molecular O—H⋯N hydrogen bonds with graph-set motif S(6). The unobserved lone pairs of the N atoms are presumed to be disposed in a syn conformation, being only the second example of an exception to the typical ‘rabbit-ears’ effect in 1,2-di­amines.
doi:10.1107/S1600536813015092
PMCID: PMC3772488  PMID: 24046631
6.  Acetonyltriphenyl­phospho­nium nitrate 
Crystals of the title salt, C21H20OP+·NO3 −, are composed of acetonyltriphenyl­phospho­nium cations and nitrate anions that mainly inter­act through electrostatic forces. The P atom in the cation has a slightly distorted tetra­hedral environment, with C—P—C angles ranging from 104.79 (7) to 112.59 (6)°. The sum of O—N—O angles of the nitrate anion is 359.99°, reflecting its trigonal–planar character. C—H⋯O hydrogen bonds help to consolidate the crystal packing.
doi:10.1107/S1600536813002110
PMCID: PMC3569822  PMID: 23424568
7.  meso-4,4′-Difluoro-2,2′-{[(3aR,7aS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-di­yl]bis­(methyl­ene)}diphenol 
In the crystal structure of the title compound, C21H24F2N2O2, there are two intra­molecular O—H⋯N hydrogen bonds involving the N atoms of the imidazolidine ring and the hy­droxy groups. The crystal studied was a meso compound obtained by the reaction of the aminal (2S,7R,11S,16R)-1,8,10,17-tetra­aza­penta­cyclo­[8.8.1.18,17.02,7.011,16]cosane with 4-fluoro­phenol. The imidazolidine ring has a twisted conformation with a CH—CH—N—CH2 torsion angle of 44.99 (14)° and, surprisingly, the lone pairs of the N atoms are disposed in a syn isomerism, making the title compound an exception to the typical ‘rabbit-ear effect’ in 1,2-diamines. In the crystal, molecules are linked via C—H⋯F hydrogen bonds, forming chains along the c-axis direction. These chains are linked via another C—H⋯F hydrogen bond, forming a three-dimensional network.
doi:10.1107/S1600536813000305
PMCID: PMC3569752  PMID: 23424498
8.  1,3-Dibenzyl-2-(2-chloro­phen­yl)-4-methyl­imidazolidine 
In the title compound, C24H25ClN2, the methine, methyl­ene and methyl C atoms of the methyl-substituted imidazolidine ring are disordered over two sets of sites with a refined occupancy ratio of 0.834 (4):0.166 (4). Each disordered ring assumes an envelope conformation with an N atom as the flap. The pendant benzyl rings are oriented equatorially with respect to the imidazolidine ring. The chloro­phenyl ring is inclined to the mean plane of the four planar atoms of the major component of the imidazolidine ring by 76.27 (12)°. The dihedral angles between the chloro­phenyl ring and the two benzyl rings are 55.31 (9) and 57.50 (8)°; the dihedral angle between these latter rings is 71.59 (9)°. In the crystal, mol­ecules are linked by C—H⋯Cl inter­actions and a number of weak C—H⋯π inter­actions, involving all three aromatic rings, forming a three-dimensional structure.
doi:10.1107/S1600536812047575
PMCID: PMC3589010  PMID: 23476246
9.  2,2′-[1,2-Phenyl­enebis(aza­nedi­yl)]di­aceto­nitrile 
The title compound, C10H10N4, shows chemical but not crystallographic C 2 symmetry. The two cyano­methyl groups are located in an anti position with respect to the aromatic ring. In the crystal, mol­ecules form parallel ladder-like tapes linked through two N—H⋯N hydrogen bonds. Further weak intra­molecular N—H⋯N hydrogen bonding is responsible for the elongation of one of the Caromatic—N bonds.
doi:10.1107/S1600536812047538
PMCID: PMC3589011  PMID: 23476247
10.  4,4′-Dimethyl-2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol 
The imidazolidine ring in the title compound, C19H24N2O2, adopts a twist conformation and its mean plane (r.m.s. deviation = 0.19 Å) makes dihedral angles of 72.38 (9) and 71.64 (9)° with the two pendant aromatic rings. The dihedral angle between the phenyl rings is 55.94 (8)°. The mol­ecular structure shows the presence of two intra­molecular O—H⋯N hydrogen bonds between the phenolic hydroxyl groups and N atoms with graph-set motif S(6). In the crystal, C—H⋯O hydrogen bonds lead to the formation of chains along the b-axis direction.
doi:10.1107/S1600536812042808
PMCID: PMC3515265  PMID: 23284485
11.  (2S,7S)-10-Ethyl-1,8,10,12-tetra­aza­tetra­cyclo­[8.3.1.18,12.02,7]penta­decan-10-ium iodide 
The title chiral quaternary ammonium salt, C13H25N4 +·I−, was synthesized through the Menschutkin reaction between the cage aminal (2S,7S)-1,8,10,12-tetra­aza­tetra­cyclo­[8.3.1.18,12.02,7]penta­decane and ethyl iodide. The quaternization occurred regioselectively on the nitrogen with major sp3 character. The crystal structure consists of anions and cations separated by normal distances. Ions are not linked through C—H⋯I hydrogen bonds.
doi:10.1107/S1600536812040159
PMCID: PMC3470393  PMID: 23125806
12.  4,4′-Difluoro-2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol 
In the title compound, C17H18F2N2O2, the imidazolidine ring system exists in a twist conformation. The mean plane through this ring system forms dihedral angles of 80.8 (8)° and 66.2 (13)°, with the benzene rings. The dihedral angle between the benzene rings is 52.0 (14)°. Two intra­molecular O—H⋯N hydrogen bonds each generate S(6) ring motifs. In the crystal, weak C—H⋯O hydrogen bonds form dimers, which are connected by further C—H⋯O inter­actions.
doi:10.1107/S1600536812040329
PMCID: PMC3470394  PMID: 23125807
13.  3,3′-(Ethane-1,2-diyl)bis(6-meth­oxy-3,4-dihydro-2H-1,3-benzoxazine) mono­hydrate 
The asymmetric unit of the title compound, C20H24N2O4·H2O, contains one half-organic mol­ecule (an inversion centre generates the other half of the mol­ecule) and a half-mol­ecule of water (the O atom has site symmetry 2). The near planarity of the fused-benzene ring is illustrated by the very small deviations of all the atoms from the plane [largest deviation = 0.0092 (11) Å. The six-membered N,O-containing ring adopts a half-chair conformation. The observed N—CH2 and CH2—O bond lengths can be correlated to the manifestation of an anomeric effect in the N—CH2—O unit. In the crystal, the mol­ecules are connected into zigzag chains parallel to [001] through O—H⋯N hydrogen bonds formed between the oxazinic N atom and the solvent water mol­ecule. The chains are consolidated by C—H⋯O inter­actions.
doi:10.1107/S1600536812035519
PMCID: PMC3435746  PMID: 22969617
14.  [μ-N,N′-Bis(2-amino­eth­yl)ethane-1,2-diamine-κ4 N 1,N 1′:N 2,N 2′]bis­{[N,N′-bis­(2-amino­eth­yl)ethane-1,2-diamine-κ4 N,N′,N′′,N′′′]cadmium} tetra­kis­(perchlorate) 
The centrosymmetric dinuclear cadmium title complex, [Cd2(C6H18N4)3](ClO4)4, was obtained by the reaction of N,N′-bis­(2-amino­eth­yl)ethane-1,2-diamine (trien) with Cd(NO3)2·4H2O and sodium perchlorate in methanol. The CdII cation is coordinated by four N atoms of a non-bridging trien ligand and by two N atoms of a bridging trien ligand in a slightly distorted octa­hedral coordination geometry. The bridging ligand shares another two N atoms with a neighboring symmetry-equivalent CdII cation. The structure displays C—H⋯O and N—H⋯O hydrogen bonding. The perchlorate anion is disordered over two sets of sites in a 0.854 (7): 0.146 (7) ratio.
doi:10.1107/S1600536812033880
PMCID: PMC3435582  PMID: 22969455
15.  4-[(E)-(4-Eth­oxy­phen­yl)imino­meth­yl]phenol 
In the title compound, C15H15NO2, the dihedral angle between the benzene rings is 52.04 (5)° and the mol­ecule has an E conformation about the central C=N bond. In the crystal, mol­ecules are connected by O—H⋯N hydrogen bonds, forming zigzag chains along the b axis. The crystal packing also features weak C—H⋯O inter­actions.
doi:10.1107/S1600536812034253
PMCID: PMC3435674  PMID: 22969545
16.  (E)-4-[(4-Bromo­phen­yl)imino­meth­yl]-2-meth­oxy­phenol 
In the crystal structure of the title compound, C14H12BrNO2, the dihedral angle between the rings is 37.87 (10)° and the mol­ecule has an E conformation about the central C=N bond. In the crystal, mol­ecules are connected by inter­molecular O—H⋯N hydrogen bonds into zigzag chains running parallel to the b axis. The packing also features C—H⋯O inter­actions.
doi:10.1107/S1600536812031704
PMCID: PMC3414922  PMID: 22904909
17.  1,3-Dinitro­soimidazolidine 
The title compound, C3H6N4O2, exhibits partial disorder with the refined occupancy ratios of the two components being 0.582 (5):0.418 (5). In the major component, the nitroso groups have a relative syn spatial arrangement [O=N⋯N=O pseudo-torsion angle = 1.1 (4)°], whereas the other component has an anti disposition [177.6 (1)°]. The N—N=O moieties are almost coplanar with a dihedral angle of 5.3 (3)°, while in the minor occupied set of atoms, this angle is 8 (1)°. In both components, the imidazolidine ring adopts a twisted conformation on the C—C bond and the crystal structure shows the strain of this ring according to the N—CH2—CH2—N torsion angles [25.9 (5) and −23.8 (7)°]. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds.
doi:10.1107/S1600536812030796
PMCID: PMC3414354  PMID: 22904887
18.  2-[(4-Meth­oxy-2-nitro­phen­yl)imino­meth­yl]phenol 
The crystal structure of the title compound, C14H12N2O4, contains four crystallographically independent mol­ecules in the asymmetric unit. All the mol­ecules have similar conformations; the dihedral angles between the aromatic rings are 33.1 (1), 33.76 (9), 31.41 (9) and 32.56 (10)°. Intra­molecular O—H⋯N hydrogen bonds form S(6) ring motifs in each molecule. In the crystal, there are two pairs of pseudo-inversion-related mol­ecules. Along the c axis, mol­ecules are stacked with π–π inter­actions between the 2-hy­droxy­phenyl and 4-meth­oxy-2-nitro­phenyl rings [centroid–centroid distances = 3.5441 (12)–3.7698 (12) Å].
doi:10.1107/S1600536812031212
PMCID: PMC3414359  PMID: 22904892
19.  [N,N′-Bis(2,3,4-trimeth­oxy­benzyl­idene)­ethane-1,2-diamine-κ2 N,N′]dibromido­mercury(II) 
In the title compound, [HgBr2(C22H28N2O6)], the HgII ion is bonded to two Br− ions and two N atoms of the chelating Schiff base ligand in a distorted tetra­hedral geometry. The Schiff base ligand adopts an E,E conformation. The dihedral angle between the planes of the two halves of the central N,N′-dimethyl­ethylenediamine part of the ligand is 2.3 (11)°. The crystal studied was twinned by pseudomerohedry [twin law (0-10/-100/00-1)]; the contribution of the minor twin component refined to 0.208 (3).
doi:10.1107/S1600536812030577
PMCID: PMC3414113  PMID: 22904720
20.  [4-Bromo-N-(pyridin-2-yl­methyl­idene)aniline-κ2 N,N′]iodido(triphenyl­phosphane-κP)copper(I) 
In the title compound, [CuI(C12H9BrN2)(C18H15P)], the CuI ion is bonded to one I atom, one triphenyl­phosphane P atom and two N atoms of the diimine ligand in a distorted tetra­hedral geometry. The Schiff base acts as a chelating ligand and coordinates to the CuI atom via two N atoms. In the diimine ligand, the dihedral angle between the pyridine and bromo­phenyl rings is 19.2 (2)°. In the crystal, mol­ecules are connected by π–π stacking inter­actions between inversion-related pyridine rings [centroid–centroid distance = 3.404 (3) Å].
doi:10.1107/S160053681202884X
PMCID: PMC3393242  PMID: 22807702
21.  2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium chloride 
In the crystal structure of the title compound, C4H8N3O+·Cl−, N—H⋯Cl hydrogen bonds link the components into chains along [010]. In addition, weak C—H⋯Cl hydrogen bonds link the chains into a two-dimensional network perpendicular to (001).
doi:10.1107/S1600536812027080
PMCID: PMC3393986  PMID: 22798851
22.  [N,N′-Bis(2,6-dichloro­benzyl­idene)propane-1,3-diamine-κ2 N,N′]dibromidozinc 
In the title compound, [ZnBr2(C17H14Cl4N2)], the ZnII ion is bonded to two bromide ions and two N atoms of the diimine ligand and displays a moderately distorted tetra­hedral coordination geometry. The Schiff base ligand acts as a chelating ligand and coordinates to the ZnII atom via two N atoms.
doi:10.1107/S1600536812027997
PMCID: PMC3393222  PMID: 22807790
23.  Methyl 2-{4-chloro-2-[5-chloro-2-(2-meth­oxy-2-oxoeth­oxy)benz­yl]phen­oxy}acetate 
In the crystal structure of the title compound, C19H18Cl2O6, mol­ecules are connected via weak C—H⋯π inter­actions into closely packed dimers.
doi:10.1107/S160053681202555X
PMCID: PMC3393330  PMID: 22807887
24.  2,17-Dichloro-8,9,10,11-tetra­hydro-19H-dibenzo[k,n][1,10,4,7]dioxadiaza­cyclo­penta­decine-7,12(6H,13H)-dione 
In the crystal structure of the title compound, C19H18Cl2N2O4, N—H⋯O hydrogen bonds link the mol­ecules into infinite chains along the b axis. The structure also features weak C—H⋯O and C—H⋯Cl hydrogen bonds and C—H⋯π and (lone pair)⋯π inter­actions [Cl⋯centroid = 3.5871 (7) Å]. An intra­molecular N—H⋯O bond occurs.
doi:10.1107/S1600536812020351
PMCID: PMC3379293  PMID: 22719491
25.  5,11,17,23,29,35-Hexa-tert-butyl-37,38,39,40,41,42-hexa­kis­(eth­oxy­carbonyl­meth­oxy)calix[6]arene acetonitrile disolvate 
In the title compound, C90H120O18·2CH3CN, the calix[6]arene has a 1,2,3-alternate conformation and possesses inversion symmetry. It crystallizes as an acetonitrile disolvate, with a half-mol­ecule of calix[6]arene and one mol­ecule of solvent in the asymmetric unit. In the crystal, the two solvent mol­ecules are enclosed in voids between the calix[6]arene mol­ecules. They form weak C—H⋯O hydrogen bonds involving an O atom of the lower rim substituent. The cavity of the calix[6]arene itself is enclosed by two opposite phenol rings, which are turned into the cavity due to the presence of a C—H⋯π inter­action. The calix[6]arene mol­ecule exhibits disorder of one substituent on its lower rim [occupancy ratio 0.897 (3):0.103 (3)].
doi:10.1107/S1600536812015735
PMCID: PMC3344542  PMID: 22590304

Results 1-25 (86)