Journot, Guillaume

2012-7-15, Journot, Guillaume, Stoeckli-Evans, Helen, Neier, Reinhard

The Rothemund-type condensation of methoxycarbonylpyrrole with acetone produces mainly the α,β'-linked dipyrromethane, a building block for the synthesis of N-confused macrocycles. The influence of the reaction conditions on the regioselectivity of the process is reported. The x-ray structures of the α,α'-, α,β'- and β,β'-linked dipyrromethanes show an interesting discrimination of the structurally different types of hydrogen bonds. [on SciFinder(R)]

2012, Journot, Guillaume, Neier, Reinhard, Stoeckli-Evans, Helen

In the title compds., C11H18N2, (II), and C13H20N2O, (III), the pyrrolidine rings have twist conformations. Compd. (II) crystallizes with two independent mols. (A and B) in the asym. unit. The mean planes of the pyrrole and pyrrolidine rings are inclined to one another by 89.99 (11) and 89.35 (10)° in mols. A and B, resp. In (III), the amide deriv. of (II), the same dihedral angle is much smaller, at only 13.42 (10)°. In the crystal structure of (II), the individual mols. are linked via N-H···N hydrogen bonds to form inversion dimers, each with an R22(12) graph-set motif. In the crystal structure of (III), the mols. are linked via N-H···O hydrogen bonds to form inversion dimers with an R22(16) graph-set motif. [on SciFinder(R)]

2010, Journot, Guillaume, Neier, Reinhard, Stoeckli-Evans, Helen

The achiral 4,4-bis(1H-pyrrol-2-yl)pentanol, C13H18N2O, crystd. in the chiral monoclinic space group P21. The pyrrole rings are inclined to 1 another by 62.30(11)°, and the PrOH chain is in an extended conformation. In the crystal, the 2 pyrrole NH groups are involved in intermol. N-H···O H bonds, giving a helical arrangement propagating along the b axis. An interesting feature of the crystal structure is the absence of any conventional H bonds involving the hydroxy H atom. There is a weak intermol. O-H···? interaction involving 1 of the pyrrole rings. Crystallog. data are given. [on SciFinder(R)]

2012, Journot, Guillaume, Neier, Reinhard, Stoeckli-Evans, Helen

In the title compd., C35H47ClN4O, the two pyrrolidine rings have envelope conformations. The conformation of the macrocycle is stabilized by N-H···N H bonds and a C-H···N interaction. The benzoyl ring is inclined to the adjacent pyrrole ring by 11.66(11)°, with a centroid-centroid distance of 3.7488(13) Å. In the crystal, mols. are linked by N-H···O H bonds into helical chains propagating in [010] and C-H···O and C-H···? interactions are also obsd. [on SciFinder(R)]

2012, Journot, Guillaume, Neier, Reinhard, Stoeckli-Evans, Helen

In the title compd., C11H23NO2, the piperidine ring has a chair conformation. The two hydroxy H atoms are disordered over two positions with fixed occupancy ratios of 0.57:0.43 and 0.63:0.37. In the mol., there are two short N-H···O interactions. In the crystal, four symmetry-related mols. are linked by O-H···O H bonds to form a cage-like arrangement, centered about the point of intersection of three 2-fold axes. These cages stack along the [100] direction. Crystallog. data and at. coordinates are given. [on SciFinder(R)]

2012, Journot, Guillaume, Neier, Reinhard, Stoeckli-Evans, Helen

In the title compd., C36H50N4O2, the two pyrrolidine rings have envelope conformations. The conformation of the macrocycle is stabilized by N-H···N H bonds and a C-H···N interaction. The benzoyl ring is inclined to an adjacent pyrrole ring by 6.76(9)°, with a centroid-to-centroid distance of 3.6285(10) Å. In the crystal, apart from a C-H···O and a C-H···? interaction, mols. are linked via an N-H···O H bond, giving helical chains propagating along [010]. Crystallog. data and at. coordinates are given. [on SciFinder(R)]

2010, Journot, Guillaume, Neier, Reinhard, Stoeckli-Evans, Helen

2,2'-(Propane-2,2-diyl)bis(1H-pyrrole), C11H14N2, crystd. with 2 independent mols. (A and B) in the asym. unit. The 2 mols. differ only slightly, with the pyrrole rings being inclined to 1 another at a dihedral angle of 87.67(8)° in mol. A and 88.09(7)° in mol. B. In the crystal, there are no classical H bonds, but the 2 pyrrole NH groups of 1 mol. are involved in N-H···? interactions with the pyrrole rings of the other mol. In this manner, a compact box-like arrangement of the 2 independent mols. is formed. Crystallog. data are given. [on SciFinder(R)]