Publications (32)39.62 Total impact
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Article: 3,7,11-Tris{4-[(1R,3S,4S)-neomenth-yl-oxy]phen-yl}tri[1,2,4]triazolo[4,3-a:4',3'-c:4'',3''-e][1,3,5]triazine-chloro-form-ethanol (1/1/1).
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ABSTRACT: The title compound, CHNO·CHCl·CHOH, was prepared by a threefold nucleophilic substitution of -neomenthyloxyphenyl-tetra-zole on cyanuric chloride followed by threefold cyclo-elimination of nitro-gen and ring closure. The central tris-triazolotriazine is roughly planar with a maximum deviation of 0.089 (7) Å but the adjacent benzene rings are twisted out of this plane. N-C-C-C torsion angles of -80.2 (9), 159.3 (7) and 50.6 (10)° destroy the formal 3 symmetry. Cavities are found between the phen-oxy residues: one is occupied by a chloro-form mol-ecule, another by ethanol forming a hydrogen bond to a triazole ring while two isopropyl groups point into the third void. One methyl group and the chloro-frm mol-ecule are disorderd and were refined using a split model.Acta Crystallographica Section E Structure Reports Online 03/2013; 69(Pt 3):o365-6. · 0.35 Impact Factor -
Article: 5,11-Dimethyl-6,12-dimeth-oxy-indolo[3,2-b]carbazole.
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ABSTRACT: The title compound, C(22)H(20)N(2)O(2), was prepared in a twofold Cadogan cyclization followed by double N-methyl-ation. The crystal structure is characterized by a zigzag arrangement of centrosymmetric mol-ecules. The indolocarbazole framework is essentially planar [maximum deviation = 0.028 (2) Å] and the meth-oxy groups are orthogonal to this plane [C-C-O-C torsion angle = -88.2 (2)°]. The lengths of the C-N bonds are nearly identical and all C-C bonds of the pyrrole subunit are significantly longer than the C-C bonds in the benzene rings.Acta Crystallographica Section E Structure Reports Online 02/2013; 69(Pt 2):o255. · 0.35 Impact Factor -
Article: 6,12-Bis(hex-yloxy)-5H,11H-indolo[3,2-b]carbazole.
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ABSTRACT: The title compound, CHNO, was prepared in a twofold Cadogan cyclization. The mol-ecule is located about a center of inversion. The indolocarbazole skeleton is essentially planar [maximum deviation = 0.028 (2) Å], the C-N bond lengths are nearly identical and the C-C bond lengths of the pyrrole unit are significantly longer than those of the benzene subunits.Acta Crystallographica Section E Structure Reports Online 01/2013; 69(Pt 1):o116-7. · 0.35 Impact Factor -
Article: The Iodocyclization of o-Alkynylbenzamides Revisited: Formation of Isobenzofuran-1(3H)-imines and 1H-Isochromen-1-imines instead of Lactams.
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ABSTRACT: The iodocyclization of o-alkynylbenzamides with various electrophiles has been reported to yield five- or six-membered lactams by nucleophilic attack of the amide nitrogen onto the triple bond. While the formation of an isobenzofuran-1(3H)-imine with two bulky substituents under Larock-conditions was initially attributed to steric hindrance, we found out that cyclization via the amide oxygen is the rule rather than the exception. Thus, the structures of the products reported in literature need to be revised.The Journal of Organic Chemistry 10/2012; · 4.45 Impact Factor -
Article: (2E,4R,5R,6S)-2-(4,5,6-Trihy-droxy-cyclo-hex-2-en-1-yl-idene)acetonitrile.
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ABSTRACT: The crystal structure of the title compound, C(8)H(9)NO(3), is characterized by a complex three-dimensional hydrogen-bond network in which every mol-ecule is connected to six symmetry-related neighbours.Acta Crystallographica Section E Structure Reports Online 09/2012; 68(Pt 9):o2737. · 0.35 Impact Factor -
Article: Decachloro-hexa-1,5-diene.
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ABSTRACT: The title compound, C(6)Cl(10), cystallizes in a nearly C2-symmetrical gauche conformation. Both trichloro-vinyl groups are nearly planar [Cl-C-C-Cl torsion angles = -178.47 (12) and -179.93 (11)°] and the lengths of their C-Cl bonds increase from the terminal trans and cis C-Cl bonds to the inter-nal bonds. The Cl-C-Cl bond angles of the terminal dichloro-methyl-ene units are compressed to 111.75 (11) and 111.40 (11)°.Acta Crystallographica Section E Structure Reports Online 06/2012; 68(Pt 6):o1685. · 0.35 Impact Factor -
Article: 2,7-Bis(2-nitro-phen-yl)-9-octyl-9H-carbazole.
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ABSTRACT: The title compound, C(32)H(31)N(3)O(4), was obtained in a Suzuki coupling of carbazole diboronic acid and bromo-nitro-benzene. In the crystal, the mol-ecule adopts a non-symmetric conformation. The carbazole ring system is approximately planar [maximum deviation from the least-squares plane = 0.039 (2) Å]. The planes of the carbazole unit and the benzene rings subtend dihedral angles of 48.42 (7) and 41.81 (6)°. The dihedral angles between the planes of the nitro-phenyl rings and the nitro groups are 44.34 (19) and 61.64 (15)°. The crystal is built from two strands of parallel mol-ecules with inter-digitated octyl chains. These strands are symmetry related by a twofold screw axis.Acta Crystallographica Section E Structure Reports Online 04/2012; 68(Pt 4):o1249. · 0.35 Impact Factor -
Article: 4-[2-(Benzyl-amino)-phen-yl]-2,6-dimethyl-quinoline N-oxide.
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ABSTRACT: The title compound, C(24)H(22)N(2)O, was obtained in a two-step procedure from the corresponding 4-(2-iodo-phen-yl)quinoline. The quinoline system is approximately planar [maximum deviation from the least-squares plane = 0.021 (2) Å]. The planes of the quinoline system and the phenyl ring subtend a dihedral angle of 78.08 (8)°. In the crystal, pairs of mol-ecules are connected via a center of symmetry and linked by a pair of angular N-H⋯O hydrogen bond. These dimers form columns oriented along the c axis.Acta Crystallographica Section E Structure Reports Online 04/2012; 68(Pt 4):o1106. · 0.35 Impact Factor -
Article: 1,4-Dihex-yloxy-2,5-bis-(2-nitro-phen-yl)benzene.
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ABSTRACT: The title compound, C(30)H(36)N(2)O(6), was prepared via twofold Suzuki coupling of a diboronic acid with bromo-nitro-benzene. The mol-ecule is located on a crystallographic inversion centre. The lateral benzene ring and the central ring make a dihedral angle of 48.75 (14)° and the nitro group is twisted by 41.47 (13)° out of the plane of the benzene ring. The nitro and hex-yloxy groups are in close proximity and the hex-yloxy chain adopts an all-anti conformation.Acta Crystallographica Section E Structure Reports Online 04/2012; 68(Pt 4):o1022. · 0.35 Impact Factor -
Article: rac-4-{(E)-[1-Cyano-1-cyclo-hexyl-2-(1H-indol-3-yl)eth-yl]imino-meth-yl}benzonitrile.
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ABSTRACT: A phosphine-catalysed addition of gramine to an alkyl-idene-amino-nitrile gives the title compound, C(25)H(24)N(4), in good yield. In the crystal, pairs of mol-ecules are connected via N-H⋯N hydrogen bonds into inversion dimers. The mol-ecules are characterized by a planar indole moiety [maximum deviation = 0.012 (1) Å], a chair conformation of the cyclo-hexane ring and an anti-periplanar conformation of the H atom on the cyclo-hexane and the adjacent cyano group.Acta Crystallographica Section E Structure Reports Online 12/2011; 67(Pt 12):o3435. · 0.35 Impact Factor -
Article: 4-Diethyl-amino-3,5-diisopropyl-benzalde-hyde.
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ABSTRACT: The title benzaldehyde, C(17)H(27)NO, was prepared via lithia-tion of bromoaniline and reaction with DMF. In the crystal, the molecule adopts a C2-symmetrical conformation; nevertheless, two modes of disorder are present: the orientation of the aldehyde group (occupancy ratio 0.5:0.5) and of symmetry-equivalent ethyl groups [occupancy ratio 0.595 (7):0.405 (7)]. The phenyl-ene ring and the carbonyl group are essentially coplanar [C-C-C-O torsion angle = -179.0 (4)°] but the dihedral angle between the mean planes of the phenyl-ene ring and the amino group = 67.5 (2)°. This and the long [1.414 (3) Å] aniline C-N bond indicate electronic decoupling between the carbonyl and amino groups. The angle sum of 359.9 (2)° around the N atom results from steric compression-induced rehybridization.Acta Crystallographica Section E Structure Reports Online 12/2011; 67(Pt 12):o3336. · 0.35 Impact Factor -
Article: 6-Chloro-3-(3-methyl-phen-yl)-1,2,4-triazolo[4,3-b]pyridazine.
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ABSTRACT: The title compound, C(12)H(9)ClN(4), was prepared from dichloro-pyridazine and tolyl-tetra-zole in a nucleophilic biaryl coupling followed by thermal ring transformation. The mol-ecule is essentially planar (r.m.s. deviation for all non-H atoms = 0.036 Å) and an intra-molecular C-H⋯N hydrogen bond occurs. In the crystal, the mol-ecules form dimers connected via π-π inter-actions [centroid-centroid distance = 3.699 (2) Å], which are further connected to neighbouring mol-ecules via C-H-N bonds. The bond lengths in the pyridazine ring system indicate a strong localization of the double bonds and there is a weak C-Cl bond [1.732 (3) Å].Acta Crystallographica Section E Structure Reports Online 10/2011; 67(Pt 10):o2551. · 0.35 Impact Factor -
Article: 3-(9H-Carbazol-9-yl)-2H-chromen-2-one.
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ABSTRACT: The title compound, C(21)H(13)NO(2), was prepared as an example of a new synthesis of carbazoles from a cyclic dibenzo-iodo-lium salt via a twofold Pd-catalysed aryl-ation of a primary amine. The two essentially planar π-subsystems [maximum deviations from the mean square plane of 0.038 (2) Å in the carbazole and 0.059 (2) Å in the coumarine unit] open a dihedral angle of 63.05 (4)°. Two mol-ecules form a centrosymmetrical pair connected via π-π inter-actions between the pyrrole and pyrone rings [centroid-centroid distance = 3.882 (1) Å] and one benzene of the carbazole and the pyrone unit [centroid-centroid distance 3.824 (1) Å]. The lattice is stabilized by C-H⋯O bridging to both coumarin O atoms.Acta Crystallographica Section E Structure Reports Online 09/2011; 67(Pt 9):o2494. · 0.35 Impact Factor -
Article: 5-Benzyl-5H-pyrido[3,2-b]indole.
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ABSTRACT: The title compound, C(18)H(14)N(2), was prepared by twofold Pd-catalyzed aryl-amination of a cyclic pyrido-benzo-iodo-lium salt. In the crystal, two mol-ecules of 9-benzyl-δ-carboline form centrosymmetrical dimers with distances of 3.651 (2) Å between the centroids of the pyridine rings and 3.961 (2) Å between the centroids of the pyrrole and pyridine rings. The phenyl rings point to the other mol-ecule in the dimer and the carboline core is essentially planar [maximum deviation of 0.027 (2) Å].Acta Crystallographica Section E Structure Reports Online 09/2011; 67(Pt 9):o2341. · 0.35 Impact Factor -
Article: (E,E,E,E)-2,3,5,6-Tetra-kis{2-[4-(dimethyl-amino)-phen-yl]ethen-yl}pyrazine.
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ABSTRACT: In the title compound, C(44)H(48)N(6), the essentially planar mol-ecule [maximum deviation from the mean plane of the π system of 0.271 (3) Å] is located on a crystallographic centre of inversion. The almost planar (angle sums at N atoms = 357.6 and 357.1°) dimethyl-amino groups and short C-N bonds of the aniline groups [both 1.379 (4) Å] indicate strong electronic coupling between these groups and the central pyrazine ring.Acta Crystallographica Section E Structure Reports Online 06/2011; 67(Pt 6):o1553. · 0.35 Impact Factor -
Article: Methyl 1-(7-acetamido-5,8-dimeth-oxy-quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl-ate.
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ABSTRACT: The title compound, C(27)H(24)N(4)O(5), is an inter-mediate in the synthesis of lavendamycin via a ruthenium-catalysed [2 + 2 + 2] cyclo-addition. An intra-molecular hydrogen-bond bridge from the carboline to the quinoline stabilizes a highly planar geometry [maximum deviation = 0.065 (6) Å] for the two rigid units. This hydrogen-bond-stabilized coplanarity has a very close analogy in the structure of the anti-tumor anti-biotic streptonigrin in the solid state and in solution. Inter-molecular hydrogen-bond bridges of amides groups along the a axis and π-π stacking inter-actions [centroid-centroid distance = 3.665 (9) Å] connect mol-ecules arranged in a parallel manner.Acta Crystallographica Section E Structure Reports Online 06/2011; 67(Pt 6):o1497-8. · 0.35 Impact Factor -
Article: 2,5-Bis[4-(dimethyl-amino)-phen-yl]-3,6-dimethyl-pyrazine.
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ABSTRACT: The title compound, C(22)H(26)N(4), was prepared from p-dimethyl-amino-propiophenone in six steps. The mol-ecule has no crystallographic symmetry. The dihedral angles between the pyrazine ring and the phenyl rings are 35.81 (6) and 37.11 (8)°. The dimethyl-amino groups are essentially planar (sum of the bond angles at N = 359.3 and 359.9°) and nearly coplanar with the adjacent aromatic ring [dihedral angles = 5.54 (11) and 7.40 (3)°]. This effect and the short aniline C-N bonds can be rationalised in terms of charge transfer from the amino groups to the central pyrazine ring.Acta Crystallographica Section E Structure Reports Online 06/2011; 67(Pt 6):o1425. · 0.35 Impact Factor -
Article: N,N-Dihexyl-4-[2-(4-nitro-phen-yl)vin-yl]aniline.
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ABSTRACT: The title compound, C(26)H(36)N(2)O(2), was prepared by Horner olefination of p-dihexyl-amino-benzaldehyde and diethyl p-nitro-benzyl-phospho-nate. It crystallizes with two independent mol-ecules in the asymmetric unit. Both have similar geometries of the π-systems but the conformations of all hexyl chains are different. Whereas one hexyl chain of the first mol-ecule shows the typical all-anti conformation, the second is arranged in a gauche-anti-gauche-anti conformation with N-C-C-C, C-C-C-C, C-C-C-C and C-C-C-C torsion angles of -65.1 (4), 167.3 (3), 63.3 (4), and 179.4 (3)°. One of the hexyl chains in the other mol-ecule has an anti-anti-gauche-anti conformation [N-C-C-C, C-C-C-C, C-C-C-C and C-C-C-C torsion angles = 179.6 (3), -179.8 (3), -68.7 (5) and -178.8 (4)°], the other starts with an anti-gauche-gauche sequence. Molecules A and B are composed of five planar subunits. The angle sums around the N atoms are in the range 356 (2)-360.0 (2)°. Torsion angles between these segments do not exceed 4.9 (4)°, except for one of the alkyl chains each [molecule A = 26.2 (4)°; molecule B = -6.0 (4)°]. The high planarity of the molecules and the short aniline C-N bonds [1.385 (3) Å in molecule A and 1.378 (3) Å in molecule B] indicate a strong electronic coupling through the stilbene unit. One methylene group is disordered over two positions with an occupancy ratio of 0.72:0.28.Acta Crystallographica Section E Structure Reports Online 06/2011; 67(Pt 6):o1384-5. · 0.35 Impact Factor -
Article: 5-Methyl-3-(3-methyl-phen-yl)-7-phenyl-1,2,4-triazolo[4,3-c]pyrimidine.
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ABSTRACT: The title compound, C(19)H(16)N(4), is one of the few known 3,7-diaryl-1,2,4-triazolo[4,3-c]pyrimidines. The triazolopyrimidine unit is essentially planar (r.m.s. deviation = 0.048 Å). The phenyl ring and the heterocyclic core subtend a dihedral angle of only 15.09 (6)°, whereas the m-tolyl ring is twisted by 71.80 (6)° out of the plane of the triazole ring. Two C-H⋯N hydrogen bonds and π-π stacking inter-actions [centroid-centroid distance = 3.7045 (8) Å] stabilize the crystal packing.Acta Crystallographica Section E Structure Reports Online 04/2011; 67(Pt 4):o987. · 0.35 Impact Factor -
Article: 2,5-Bis{2,2-bis-[4-(dimethyl-amino)-phen-yl]ethen-yl}-N,N'-diphenyl-N,N'-dipropyl-benzene-1,4-diamine.
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ABSTRACT: The title compound, C(60)H(68)N(6), was prepared by Horner olefination of a terephthaldialdehyde and a diaryl-methyl phospho-nate. There is one half-mol-ecule, located on an inversion centre, in the asymmetric unit. The dihedral angle between the plane of the vinyl-ene unit and the central ring is 36.79 (15)°, while those between the vinyl-ene unit and the lateral phenyl rings are 53.04 (10) and 53.74 (9)°.Acta Crystallographica Section E Structure Reports Online 04/2011; 67(Pt 4):o876. · 0.35 Impact Factor
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Institutions
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1999–2013
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Johannes Gutenberg-Universität Mainz
- • Institute of Organic Chemistry
- • Institute of Inorganic and Analytical Chemistry
Mainz, Rhineland-Palatinate, Germany
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