Browsing by Author "Gerber, T."

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1,5-Dibromo-2,4-dimethoxybenzene
(2012) Vijesh, A.M.; Isloor, A.M.; Gerber, T.; Brecht, B.V.; Betz, R.
In the title compound, C8H8Br2O2, all non-H atoms lie essentially in a common plane (r.m.s deviation of all fitted non-H atoms = 0.0330 ). In the crystal, weak C-H?O hydrogen bonds connect the molecules, forming chains which extend along the b-axis direction.
1,5-Dibromo-2,4-dimethoxybenzene
(2012) Vijesh, A.M.; Isloor, A.M.; Gerber, T.; Brecht, B.V.; Betz, R.
In the title compound, C8H8Br2O2, all non-H atoms lie essentially in a common plane (r.m.s deviation of all fitted non-H atoms = 0.0330 Å). In the crystal, weak C-H?O hydrogen bonds connect the molecules, forming chains which extend along the b-axis direction.
1-(4-Bromophenyl)-2-(2-chlorophenoxy)ethanone
(2012) Shenvi, S.S.; Isloor, A.M.; Gerber, T.; Hosten, E.; Betz, R.
In the title compound, C14H10BrClO2, a twofold halogenated derivative of phenylated phenyloxyethanone, the least-squares planes defined by the C atoms of the aromatic rings subtend an angle of 71.31 (17) . In the crystal, C-H?O contacts connect the molecules into chains along the b-axis direction.
1-(4-Bromophenyl)-2-(2-chlorophenoxy)ethanone
(2012) Shenvi, S.S.; Isloor, A.M.; Gerber, T.; Hosten, E.; Betz, R.
In the title compound, C14H10BrClO2, a twofold halogenated derivative of phenylated phenyloxyethanone, the least-squares planes defined by the C atoms of the aromatic rings subtend an angle of 71.31 (17)°. In the crystal, C-H?O contacts connect the molecules into chains along the b-axis direction.
1-[5-Acetyl-2,6-dimethyl-4-(5-phenyl-1H-pyrazol-3-yl)-1, 4-dihydropyridin-3-yl]ethanone monohydrate
(2012) Isloor, A.M.; Malladi, S.; Sundershan, S.; Gerber, T.; Hosten, E.; Betz, R.
In the title compound, C20H21N3O 2 H2O, the aza-substitued six-membered ring adopts a L4 B conformation. In the crystal, classical N-H?O, N-H?N and O-H?O hydrogen bonds connect the entities into a three-dimensional network. Intramolecular C-H?O contacts are also observed.
1-[5-Acetyl-2,6-dimethyl-4-(5-phenyl-1H-pyrazol-3-yl)-1, 4-dihydropyridin-3-yl]ethanone monohydrate
(2012) Islor, A.M.; Malladi, S.; Sundershan, S.; Gerber, T.; Hosten, E.; Betz, R.
In the title compound, C20H21N3O 2·H2O, the aza-substitued six-membered ring adopts a L4 B conformation. In the crystal, classical N-H?O, N-H?N and O-H?O hydrogen bonds connect the entities into a three-dimensional network. Intramolecular C-H?O contacts are also observed.
2,4-Dichlorobenzyl 2-methoxybenzoate
(2013) Isloor, A.M.; Garudachari, B.; Gerber, T.; Hosten, E.; Betz, R.
In the title compound, C15H12Cl2O 3, the aromatic rings make a dihedral angle of 10.78 (4) . In the molecule, there is a short C-H?O contact. In the crystal, C-H?O contacts connect the molecules into C(7)C(8) chains along the b axis. The shortest intercentroid distance between two benzoic acid aromatic systems is 3.7416 (8) .
2,4-Dichlorobenzyl 2-methoxybenzoate
(2013) Isloor, A.M.; Garudachari, B.; Gerber, T.; Hosten, E.; Betz, R.
In the title compound, C15H12Cl2O 3, the aromatic rings make a dihedral angle of 10.78 (4)°. In the molecule, there is a short C-H?O contact. In the crystal, C-H?O contacts connect the molecules into C(7)C(8) chains along the b axis. The shortest intercentroid distance between two benzoic acid aromatic systems is 3.7416 (8) Å.
2-(4-Bromophenyl)-2-oxoethyl naphthalene-1-carboxylate
(2013) Garudachari, B.; Isloor, A.M.; Gerber, T.; Hosten, E.; Betz, R.
In the title compound, C19H13BrO3, an ester of 1-naphthoic acid with an aromatic alcohol, the least-squares planes defined by the C atoms of the respective aromatic systems enclose an angle of 77.20 (5) . In the crystal, C - H?O contacts connect the molecules into undulating sheets parallel (100).
2-(4-Bromophenyl)-2-oxoethyl naphthalene-1-carboxylate
(2013) Garudachari, B.; Isloor, A.M.; Gerber, T.; Hosten, E.; Betz, R.
In the title compound, C19H13BrO3, an ester of 1-naphthoic acid with an aromatic alcohol, the least-squares planes defined by the C atoms of the respective aromatic systems enclose an angle of 77.20 (5)°. In the crystal, C - H?O contacts connect the molecules into undulating sheets parallel (100).
2-(4-Chlorophenyl)-2-oxoethyl naphthalene-1-carboxylate
(2013) Garudachari, B.; Isloor, A.M.; Gerber, T.; Hosten, E.; Betz, R.
In the title compound, C19H13ClO3, an ester of 1-naphthoic acid with an aromatic alcohol, the least-squares planes defined by the C atoms of the respective aromatic systems enclose an angle of 77.16 (3) . In the crystal, C-H?O contacts connect the molecules into undulating sheets parallel to the bc plane.
2-(4-Chlorophenyl)-2-oxoethyl naphthalene-1-carboxylate
(2013) Garudachari, B.; Isloor, A.M.; Gerber, T.; Hosten, E.; Betz, R.
In the title compound, C19H13ClO3, an ester of 1-naphthoic acid with an aromatic alcohol, the least-squares planes defined by the C atoms of the respective aromatic systems enclose an angle of 77.16 (3)°. In the crystal, C-H?O contacts connect the molecules into undulating sheets parallel to the bc plane.
2-(4-Fluorophenyl)-2-oxoethyl 2-methoxy-benzoate
(2012) Isloor, A.M.; Garudachari, B.; Satyanarayan, M.N.; Gerber, T.; Hosten, E.; Betz, R.
In the title compound, C 16H 13FO 4, the aromatic rings enclose an angle of 73.68 (6) . In the crystal, C - H?O and C - H?F contacts connect the mol-ecules into a three-dimensional network. The shortest inter-centroid distance between two aromatic ?-systems is 3.6679 (7) and is apparent between the fluorinated phenyl groups.
2-(4-Fluorophenyl)-2-oxoethyl 2-methoxy-benzoate
(2012) Isloor, A.M.; Garudachari, B.; Satyanarayan, M.N.; Gerber, T.; Hosten, E.; Betz, R.
In the title compound, C 16H 13FO 4, the aromatic rings enclose an angle of 73.68 (6)°. In the crystal, C - H?O and C - H?F contacts connect the mol-ecules into a three-dimensional network. The shortest inter-centroid distance between two aromatic ?-systems is 3.6679 (7) Å and is apparent between the fluorinated phenyl groups.
(2E)-1-(2,4-Dichlorophenyl)-3-[3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl] prop-2-en-1-one
(2012) Isloor, A.M.; Malladi, S.; Gerber, T.; Brecht, B.V.; Betz, R.
In the title compound, C 24H 15Cl 2N 3O 3, the C=C double bond is E configured. The 1-phenyl-1H-pyrazole moiety is roughly planar (r.m.s. deviation of all fitted non-H atoms = 0.0780 ), but the mean planes of the two components are inclined at an angle of 9.95 (7) . The mean plane defined by the non-H atoms of the 1H-pyrazole ring encloses angles of 9.95 (7), 24.54 (6) and 43.02 (6) with the mean planes of the different benzene rings. In the crystal, C - H?O contacts are present and result in the formation of a double-layer two-dimensional network lying parallel to (110). The shortest inter-centroid distance between two aromatic systems is 3.5455 (7) and is apparent between two pyrazole systems. Further ?-? interactions are manifest between a pair of 4-nitrophenyl rings [centroid-to-centroid distance = 3.6443 (7) ] and a pair of 2,4-dichlorophenyl rings [centroid-to-centroid distance = 3.7797 (7) ].
(2E)-1-(2,4-Dichlorophenyl)-3-[3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl] prop-2-en-1-one
(2012) Isloor, A.M.; Malladi, S.; Gerber, T.; Brecht, B.V.; Betz, R.
In the title compound, C 24H 15Cl 2N 3O 3, the C=C double bond is E configured. The 1-phenyl-1H-pyrazole moiety is roughly planar (r.m.s. deviation of all fitted non-H atoms = 0.0780 Å), but the mean planes of the two components are inclined at an angle of 9.95 (7)°. The mean plane defined by the non-H atoms of the 1H-pyrazole ring encloses angles of 9.95 (7), 24.54 (6) and 43.02 (6)° with the mean planes of the different benzene rings. In the crystal, C - H?O contacts are present and result in the formation of a double-layer two-dimensional network lying parallel to (110). The shortest inter-centroid distance between two aromatic systems is 3.5455 (7) Å and is apparent between two pyrazole systems. Further ?-? interactions are manifest between a pair of 4-nitrophenyl rings [centroid-to-centroid distance = 3.6443 (7) Å] and a pair of 2,4-dichlorophenyl rings [centroid-to-centroid distance = 3.7797 (7) Å].
3-(4-Chlorophenyl)-5-phenyl-4,5-dihydro-1,3-oxazole
(2012) Isloor, A.M.; Yaradoni, R.; Garudachari, B.; Gerber, T.; Hosten, E.; Betz, R.
In the title compound, C15H12ClNO, the isoxazoline ring adopts an envelope conformation with the C atom bearing an unsubstituted phenyl ring as the flap atom. The chlorinated phenyl group is nearly in-plane with the four coplanar atoms of the heterocycle and the corresponding mean planes enclosing an angle of 1.16(7) . The unsubstituted phenyl group attached to the envelope flap atom approaches a nearly perpendicular orientation relative to the isoxazoline ring with a dihedral angle of 74.93(7) . In the crystal, weak C-H?O, C-H?N and C-H?? interactions connect the molecules into layers perpendicular to the a axis.
3-(4-Chlorophenyl)-5-phenyl-4,5-dihydro-1,3-oxazole
(2012) Islor, A.M.; Yaradoni, R.; Garudachari, B.; Gerber, T.; Hosten, E.; Betz, R.
In the title compound, C15H12ClNO, the isoxazoline ring adopts an envelope conformation with the C atom bearing an unsubstituted phenyl ring as the flap atom. The chlorinated phenyl group is nearly in-plane with the four coplanar atoms of the heterocycle and the corresponding mean planes enclosing an angle of 1.16(7)°. The unsubstituted phenyl group attached to the envelope flap atom approaches a nearly perpendicular orientation relative to the isoxazoline ring with a dihedral angle of 74.93(7)°. In the crystal, weak C-H?O, C-H?N and C-H?? interactions connect the molecules into layers perpendicular to the a axis.
Crystal structure of ethyl 6-methyl-4-oxo-1,4-dihydroquinoline-3- carboxylate, C13H13NO3
(2013) Garudachari, B.; Isloor, A.M.; Satyanarayan, M.N.; Gerber, T.; Hosten, E.; Betz, R.
(Equation presentation)(Table presentation) Source of material Diethyl{[(4-methylphenyl)amino]methylidene}propanedioate (1.0 g, 0.003 mol) and Dowtherm (10 mL) were heated to 250 C for 5 h. The reactionmixture was then cooled to 25 C and stirred in n-hexane (10 mL) for 10 min. The solid product obtained was filtered, dried and recrystallized from ethanol. Single crystals suitable for the X-ray diffraction study were grown by slow evaporation of a diluted ethanol solution of the compound at room temperature, yield: 0.79 g (95.1 %) [8]. Discussion Heterocyclic derivatives attract the interest ofmedicinal chemists because of their varied biological activities such as their anti-microbial [1] or analgesic [2] properties. Particularily intriguing are quinoline and its derivatives as these have already found application as anticancer [3], antiviral [4] and antimalarial [5] agents. In view of the biological importance as well as possible pharmacological applications, the title compound was synthesized to study its crystal structure. Although the title compound could be present in an aromatic form spanning the whole core of themolecule (i.e. as ethyl 4-hydroxy-6-methylquinoline-3-carboxylate), a tautomer featuring only an aromatic system on the non-heterocyclic ring is observed in the solid state. The least-squares planes defined by the respective intracyclic atoms of each of the two sixmembered rings enclose an angle of just 1.41(11) . The leastsquares plane defined by all non-hydrogen atoms of the aza-naphthalene core is essentially flat (r.m.s. of all fitted atoms = 0.015 ) with the carbon atom bearing the ester substituent deviatingmost from the plane (by 0.026(2) ). The hydrogen atom of the secondary amine group forms a hydrogen bond to the two doublebonded oxygen atom of the ester group. In terms of graph-set analysis [6, 7], the descriptor for the N-H Otype hydrogen bond necessitates a C1 1(6). In total, the molecules are connected to chains along the b direction. (Table presentation).
Crystal structure of ethyl 6-methyl-4-oxo-1,4-dihydroquinoline-3- carboxylate, C13H13NO3
(2013) Garudachari, B.; Islor, A.M.; Satyanarayan, M.N.; Gerber, T.; Hosten, E.; Betz, R.
(Equation presentation)(Table presentation) Source of material Diethyl{[(4-methylphenyl)amino]methylidene}propanedioate (1.0 g, 0.003 mol) and Dowtherm (10 mL) were heated to 250 °C for 5 h. The reactionmixture was then cooled to 25 °C and stirred in n-hexane (10 mL) for 10 min. The solid product obtained was filtered, dried and recrystallized from ethanol. Single crystals suitable for the X-ray diffraction study were grown by slow evaporation of a diluted ethanol solution of the compound at room temperature, yield: 0.79 g (95.1 %) [8]. Discussion Heterocyclic derivatives attract the interest ofmedicinal chemists because of their varied biological activities such as their anti-microbial [1] or analgesic [2] properties. Particularily intriguing are quinoline and its derivatives as these have already found application as anticancer [3], antiviral [4] and antimalarial [5] agents. In view of the biological importance as well as possible pharmacological applications, the title compound was synthesized to study its crystal structure. Although the title compound could be present in an aromatic form spanning the whole core of themolecule (i.e. as ethyl 4-hydroxy-6-methylquinoline-3-carboxylate), a tautomer featuring only an aromatic system on the non-heterocyclic ring is observed in the solid state. The least-squares planes defined by the respective intracyclic atoms of each of the two sixmembered rings enclose an angle of just 1.41(11)°. The leastsquares plane defined by all non-hydrogen atoms of the aza-naphthalene core is essentially flat (r.m.s. of all fitted atoms = 0.015 Å) with the carbon atom bearing the ester substituent deviatingmost from the plane (by 0.026(2) Å). The hydrogen atom of the secondary amine group forms a hydrogen bond to the two doublebonded oxygen atom of the ester group. In terms of graph-set analysis [6, 7], the descriptor for the N-H Otype hydrogen bond necessitates a C1 1(6). In total, the molecules are connected to chains along the b direction. (Table presentation).