Browsing by Author "Chantrapromma, S."

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2-[(4-tert-Butyl-anilino)(phen-yl)meth-yl]cyclo-hexa-none
(2009) Fun, H.-K.; Chantrapromma, S.; Rai, S.; Shetty, P.; Isloor, A.M.
In the mol-ecule of the title compound, C23H29NO, the cyclo-hexa-none ring has been distorted from the standard chair conformation by the ketone group such that part of the ring is almost flat. The remaining [(4-tert-butyl-anilino)(phen-yl)meth-yl] portion of the mol-ecule is in an equatorial position on the cyclo-hexa-none ring. The dihedral angle between the two benzene rings is 81.52 (8) . In the crystal packing, mol-ecules are linked by N - H?O hydrogen bonds into infinite one-dimensional chains along the a axis and these chains are stacked down the c axis. The crystal structure is further stabilized by weak C - H?O and C - H?? inter-actions.
2-[(4-tert-Butyl-anilino)(phen-yl)meth-yl]cyclo-hexa-none
(2009) Fun, H.-K.; Chantrapromma, S.; Rai, S.; Shetty, P.; Isloor, A.M.
In the mol-ecule of the title compound, C23H29NO, the cyclo-hexa-none ring has been distorted from the standard chair conformation by the ketone group such that part of the ring is almost flat. The remaining [(4-tert-butyl-anilino)(phen-yl)meth-yl] portion of the mol-ecule is in an equatorial position on the cyclo-hexa-none ring. The dihedral angle between the two benzene rings is 81.52 (8)°. In the crystal packing, mol-ecules are linked by N - H?O hydrogen bonds into infinite one-dimensional chains along the a axis and these chains are stacked down the c axis. The crystal structure is further stabilized by weak C - H?O and C - H?? inter-actions.
2-Methyl-5-[(3-methyl-4-nitrobenzyl)-sulfanyl]-1,3,4-thiadiazole
(2011) Fun, H.-K.; Chantrapromma, S.; Chandrakantha, B.; Isloor, A.M.; Shetty, P.
The molecule of the title thiadiazole derivative, C11H 11N3O2S2, has a butterfly-like structure and the whole molecule is disordered with a site-occupancy ratio of 0.629 (4):0.371 (4). The molecule is disordered in such a way that the 3-methyl-4-nitrophenyl units of the major and minor components are approximately related by 180 rotation around the C - N bond axis. The dihedral angle between the 1,3,4-thiadiazole and benzene rings is 70.8 (4) in the major component and 74.9 (6) in the minor component. In the crystal, molecules are arranged into screw chains along the c axis. These chains are stacked along the b axis. Weak intermolecular C - H?O and C - H?? interactions and a short C?O contact [3.005 (7) ] are present.
2-Methyl-5-[(3-methyl-4-nitrobenzyl)-sulfanyl]-1,3,4-thiadiazole
(2011) Fun, H.-K.; Chantrapromma, S.; Chandrakantha, B.; Isloor, A.M.; Shetty, P.
The molecule of the title thiadiazole derivative, C11H 11N3O2S2, has a butterfly-like structure and the whole molecule is disordered with a site-occupancy ratio of 0.629 (4):0.371 (4). The molecule is disordered in such a way that the 3-methyl-4-nitrophenyl units of the major and minor components are approximately related by 180° rotation around the C - N bond axis. The dihedral angle between the 1,3,4-thiadiazole and benzene rings is 70.8 (4) ° in the major component and 74.9 (6) ° in the minor component. In the crystal, molecules are arranged into screw chains along the c axis. These chains are stacked along the b axis. Weak intermolecular C - H?O and C - H?? interactions and a short C?O contact [3.005 (7) Å] are present.
(4-Chloro-2-fluoro-phen-yl)[1-(2,6-difluoro-phen-yl)but-3-en-yl]amine
(2009) Fun, H.-K.; Rai, S.; Shetty, P.; Isloor, A.M.; Chantrapromma, S.
In the mol-ecule of the title homoallylic amine, C16H 13ClF3N, the dihedral angle between the two benzene rings is 84.63 (4) . Weak intra-molecular N - H?F hydrogen bonds generate S(6) and S(5) ring motifs. In the crystal structure, weak inter-molecuar N - H?F hydrogen bonds link mol-ecules into centrosymmetric dimers which are arranged in mol-ecular sheets parallel to the ac plane.
(4-Chloro-2-fluoro-phen-yl)[1-(2,6-difluoro-phen-yl)but-3-en-yl]amine
(2009) Fun, H.-K.; Rai, S.; Shetty, P.; Isloor, A.M.; Chantrapromma, S.
In the mol-ecule of the title homoallylic amine, C16H 13ClF3N, the dihedral angle between the two benzene rings is 84.63 (4)°. Weak intra-molecular N - H?F hydrogen bonds generate S(6) and S(5) ring motifs. In the crystal structure, weak inter-molecuar N - H?F hydrogen bonds link mol-ecules into centrosymmetric dimers which are arranged in mol-ecular sheets parallel to the ac plane.
5-[(4-methoxybenzyl)sulfanyl]-2-methyl-1,3,4-thiadiazole
(2011) Fun, H.-K.; Chantrapromma, S.; Chandrakantha, B.; Isloor, A.M.; Shetty, P.
The title molecule, C11H12N2OS 2, is twisted with a dihedral angle of 83.63 (12) between the 1,3,4-thiadiazole and benzene rings. The methoxy group deviates slightly from the attached benzene ring, with a C - C - O - C torsion angle of 4.2 (4) . In the crystal, molecules are linked by weak C - H?N interactions and stacked along the c axis.
5-[(4-methoxybenzyl)sulfanyl]-2-methyl-1,3,4-thiadiazole
(2011) Fun, H.-K.; Chantrapromma, S.; Chandrakantha, B.; Isloor, A.M.; Shetty, P.
The title molecule, C11H12N2OS 2, is twisted with a dihedral angle of 83.63 (12)° between the 1,3,4-thiadiazole and benzene rings. The methoxy group deviates slightly from the attached benzene ring, with a C - C - O - C torsion angle of 4.2 (4)°. In the crystal, molecules are linked by weak C - H?N interactions and stacked along the c axis.
6-(4-Aminophenyl)-2-ethoxy-4-(2-thienyl)nicotinonitrile
(2010) Fun, H.-K.; Chantrapromma, S.; Kobkeatthawin, T.; Padaki, M.; Isloor, A.M.
In the title nicotinonitrile derivative, C18H15N 3OS, the central pyridyl ring makes dihedral angles of 25.22 (10) and 24.80 (16) with the 4-aminophenyl and thiophene rings, respectively. The thiophene ring is disordered over two orientations by rotation around the C(thiophene)-C(pyridine) bond; the occupancies are 0.858 (2) and 0.142 (2). The ethoxy group is slightly twisted from the attached pyridyl ring [C-O-C-C torsion angle = 171.13 (16) ]. In the crystal structure, molecules are linked by N-H?N hydrogen bonds into chains along [010]. These chains are stacked along the a axis. C-H?? weak inter-actions involving the thiophene ring are observed.
6-(4-Aminophenyl)-2-ethoxy-4-(2-thienyl)nicotinonitrile
(2010) Fun, H.-K.; Chantrapromma, S.; Kobkeatthawin, T.; Padaki, M.; Isloor, A.M.
In the title nicotinonitrile derivative, C18H15N 3OS, the central pyridyl ring makes dihedral angles of 25.22 (10) and 24.80 (16)° with the 4-aminophenyl and thiophene rings, respectively. The thiophene ring is disordered over two orientations by rotation around the C(thiophene)-C(pyridine) bond; the occupancies are 0.858 (2) and 0.142 (2). The ethoxy group is slightly twisted from the attached pyridyl ring [C-O-C-C torsion angle = 171.13 (16)°]. In the crystal structure, molecules are linked by N-H?N hydrogen bonds into chains along [010]. These chains are stacked along the a axis. C-H?? weak inter-actions involving the thiophene ring are observed.
6-(4-Bromo-phen-yl)-2-eth-oxy-4-(2,4,6-trimethoxy-phen-yl)nicotinonitrile
(2009) Chantrapromma, S.; Fun, H.-K.; Suwunwong, T.; Padaki, M.; Isloor, A.M.
In the asymmetric unit of the title nicotinonitrile derivative, C 23H21BrN2O4, there are two non-planar independent mol-ecules. The central pyridine ring makes dihedral angles of 9.05 (7) and 77.06 (7) , respectively, with the 4-bromo-phenyl and 2,4,6-trimethoxy-phenyl rings in one mol-ecule, whereas the corresponding values are 5.96 (7) and 82.37 (7) in the other. All the three meth-oxy groups are essentially in the plane of the attached benzene ring [C- O- C- C angles = 2.99 (19), 4.8 (2) and-6.2 (2) in one mol-ecule, and 2.69 (18), 176.73 (15) and 1.3 (2) in the other]. The eth-oxy group is slightly twisted in one mol-ecule [C- C- O- C = 173.84 (12) ], whereas it is coplanar with the pyridine ring in the other [C- C- O- C =-177.23 (13) ]. Weak intra-molecular C- H?N inter-actions generate S(5) ring motifs. In the crystal structure, the mol-ecules are linked by weak inter-molecular C- H?N and C- H?O inter-actions into a supra-molecular three-dimensional network in such a way that the nicotinonitrile units of neighboring mol-ecules are stacked in an anti-parallel manner along the c axis. The crystal is further stabilized by C- H?? inter-actions.
6-(4-Bromo-phen-yl)-2-eth-oxy-4-(2,4,6-trimethoxy-phen-yl)nicotinonitrile
(2009) Chantrapromma, S.; Fun, H.-K.; Suwunwong, T.; Padaki, M.; Isloor, A.M.
In the asymmetric unit of the title nicotinonitrile derivative, C 23H21BrN2O4, there are two non-planar independent mol-ecules. The central pyridine ring makes dihedral angles of 9.05 (7) and 77.06 (7)°, respectively, with the 4-bromo-phenyl and 2,4,6-trimethoxy-phenyl rings in one mol-ecule, whereas the corresponding values are 5.96 (7) and 82.37 (7)° in the other. All the three meth-oxy groups are essentially in the plane of the attached benzene ring [C- O- C- C angles = 2.99 (19), 4.8 (2) and-6.2 (2)° in one mol-ecule, and 2.69 (18), 176.73 (15) and 1.3 (2)° in the other]. The eth-oxy group is slightly twisted in one mol-ecule [C- C- O- C = 173.84 (12)°], whereas it is coplanar with the pyridine ring in the other [C- C- O- C =-177.23 (13)°]. Weak intra-molecular C- H?N inter-actions generate S(5) ring motifs. In the crystal structure, the mol-ecules are linked by weak inter-molecular C- H?N and C- H?O inter-actions into a supra-molecular three-dimensional network in such a way that the nicotinonitrile units of neighboring mol-ecules are stacked in an anti-parallel manner along the c axis. The crystal is further stabilized by C- H?? inter-actions.
6-(4-Bromo-phenyl)-2-ethoxy-4-(4-ethoxyphenyl)nicotinonitrile
(2010) Chantrapromma, S.; Fun, H.-K.; Suwunwong, T.; Padaki, M.; Isloor, A.M.
The mol-ecule of the title nicotinonitrile derivative, C22H 19BrN2O2, is non-planar, the central pyridine ring making dihedral angles of 7.34 (14) and 43.56 (15) with the 4-bromophenyl and 4-ethoxyphenyl rings, respectively. The ethoxy group of the 4-ethoxyphenyl is slightly twisted from the attached benzene ring [C-O-C-C = 174.2 (3) ], whereas the ethoxy group attached to the pyridine ring is in a (+)syn-clinal conformation [C-O-C-C = 83.0 (3) ]. A weak intra-molecular C-H?N inter-action generates an S(5) ring motif. In the crystal structure, the mol-ecules are linked by weak inter-molecular C-H?N inter-actions into screw chains along the b axis. These chains stacked along the a axis. ?-? inter-actions with centroid-centroid distances of 3.8724 (16) and 3.8727 (16) are also observed.
6-(4-Bromo-phenyl)-2-ethoxy-4-(4-ethoxyphenyl)nicotinonitrile
(2010) Chantrapromma, S.; Fun, H.-K.; Suwunwong, T.; Padaki, M.; Isloor, A.M.
The mol-ecule of the title nicotinonitrile derivative, C22H 19BrN2O2, is non-planar, the central pyridine ring making dihedral angles of 7.34 (14) and 43.56 (15)° with the 4-bromophenyl and 4-ethoxyphenyl rings, respectively. The ethoxy group of the 4-ethoxyphenyl is slightly twisted from the attached benzene ring [C-O-C-C = 174.2 (3)°], whereas the ethoxy group attached to the pyridine ring is in a (+)syn-clinal conformation [C-O-C-C = 83.0 (3)°]. A weak intra-molecular C-H?N inter-action generates an S(5) ring motif. In the crystal structure, the mol-ecules are linked by weak inter-molecular C-H?N inter-actions into screw chains along the b axis. These chains stacked along the a axis. ?-? inter-actions with centroid-centroid distances of 3.8724 (16) and 3.8727 (16) Å are also observed.
6-(4-Bromophenyl)-2-eth-oxy-4-(2,4,5-trimethoxyphenyl)nicotinonitrile
(2010) Chantrapromma, S.; Fun, H.-K.; Padaki, M.; Suwunwong, T.; Isloor, A.M.
There are two mol-ecules in the asymmetric unit of the title compound, C23H21BrN2O4, which differ in the conformation of their ethoxy residues, i.e. almost co-planar with the pyridine ring in one mol-ecule [C - O - C - C = -174.0 (2) ] but almost perpendicular in the other [C - O - C - C = 92.8 (3) ]. The dihedral angles between the central pyridine ring and the 4-bromo-phenyl and 2,4,5-trimethoxy-phenyl rings are 11.05 (12) and 63.78 (12) , respectively, in one mol-ecule; the corres-ponding angles in the other mol-ecule are 30.38 (13) and 65.38 (13) , respectively. In the crystal structure, pairs of mol-ecules are arranged in a face-to-face sandwich structure which further stacks along the b axis. The crystal packing features C - H?? inter-actions and Br?O [3.5417 (17) ], Br?C [3.748 (3) ], C?N [3.376 (4) ] and C?O [3.351 (3)-3.409 (3) ] contacts. Finally, ??? inter-actions [centroid?centroid distances = 3.6346 (19) and 3.6882 (19) ] are observed.
6-(4-Bromophenyl)-2-eth-oxy-4-(2,4,5-trimethoxyphenyl)nicotinonitrile
(2010) Chantrapromma, S.; Fun, H.-K.; Padaki, M.; Suwunwong, T.; Isloor, A.M.
There are two mol-ecules in the asymmetric unit of the title compound, C23H21BrN2O4, which differ in the conformation of their ethoxy residues, i.e. almost co-planar with the pyridine ring in one mol-ecule [C - O - C - C = -174.0 (2)°] but almost perpendicular in the other [C - O - C - C = 92.8 (3)°]. The dihedral angles between the central pyridine ring and the 4-bromo-phenyl and 2,4,5-trimethoxy-phenyl rings are 11.05 (12) and 63.78 (12)°, respectively, in one mol-ecule; the corres-ponding angles in the other mol-ecule are 30.38 (13) and 65.38 (13)°, respectively. In the crystal structure, pairs of mol-ecules are arranged in a face-to-face sandwich structure which further stacks along the b axis. The crystal packing features C - H?? inter-actions and Br?O [3.5417 (17) Å], Br?C [3.748 (3) Å], C?N [3.376 (4) Å] and C?O [3.351 (3)-3.409 (3) Å] contacts. Finally, ??? inter-actions [centroid?centroid distances = 3.6346 (19) and 3.6882 (19) Å] are observed.
Ethyl 2-[(3-chloro-phen-yl)hydrazono]-3-oxobutanoate
(2009) Fun, H.-K.; Padaki, M.; Sowmya; Isloor, A.M.; Chantrapromma, S.
The mol-ecule of the title oxobutanoate derivative, C12H 13ClN2O3, adopts a keto-hydrazo tautomeric form and is roughly planar, the angle between the benzene ring and the mean plane through the hydrazone and aliphatic chain being 1.49 (6) . This planarity is further aided by the formation of an intra-molecular N - H?O hydrogen bond which generates an S(6) ring motif. The aromatic ring and aliphatic chain have a trans configuration with respect to the N - N bond. In the crystal packing, centrosymmetric R 2 2(16) dimers are formed through pairs of weak C - H?O(3-oxo) inter-actions. These dimers are linked together through weak C - H?O(carboxyl-ate C=O) inter-actions into ribbons along the b-axis direction. These ribbons are stacked along the a-axis direction. The crystal also exhibits Cl?Cl [3.4988 (6) ] and C?O [3.167 (2)-3.335 (2) ] short contacts.
Ethyl 2-[(3-chloro-phen-yl)hydrazono]-3-oxobutanoate
(2009) Fun, H.-K.; Padaki, M.; Holla, S.R.; Isloor, A.M.; Chantrapromma, S.
The mol-ecule of the title oxobutanoate derivative, C12H 13ClN2O3, adopts a keto-hydrazo tautomeric form and is roughly planar, the angle between the benzene ring and the mean plane through the hydrazone and aliphatic chain being 1.49 (6)°. This planarity is further aided by the formation of an intra-molecular N - H?O hydrogen bond which generates an S(6) ring motif. The aromatic ring and aliphatic chain have a trans configuration with respect to the N - N bond. In the crystal packing, centrosymmetric R 2 2(16) dimers are formed through pairs of weak C - H?O(3-oxo) inter-actions. These dimers are linked together through weak C - H?O(carboxyl-ate C=O) inter-actions into ribbons along the b-axis direction. These ribbons are stacked along the a-axis direction. The crystal also exhibits Cl?Cl [3.4988 (6) Å] and C?O [3.167 (2)-3.335 (2) Å] short contacts.
Ethyl 2-[(4-chloro-phen-yl)hydrazono]-3-oxobutanoate
(2009) Fun, H.-K.; Chantrapromma, S.; Padaki, M.; Radhika; Isloor, A.M.
The mol-ecule of the title oxobutanoate derivative, C12H 13ClN2O3, is nearly planar; the inter-planar angle between the benzene ring and the mean plane through the hydrazono-3-oxobutanoate unit is 2.69 (3) . An intra-molecular N - H?O hydrogen bond generates an S(6) ring motif. In the crystal packing, C - H?O(3-oxo) inter-actions link mol-ecules into dimers. The dimers thus formed are linked through C - H?O(carboxyl-ate C=O) inter-actions, leading to the formation of ribbons along the [01 ] direction, which are stabilized via Cl?Cl [3.2916 (3) ] contacts. The ribbons are stacked via C?O contacts [3.2367 (12)-3.3948 (12) ].
Ethyl 2-[(4-chloro-phen-yl)hydrazono]-3-oxobutanoate
(2009) Fun, H.-K.; Chantrapromma, S.; Padaki, M.; Radhika; Isloor, A.M.
The mol-ecule of the title oxobutanoate derivative, C12H 13ClN2O3, is nearly planar; the inter-planar angle between the benzene ring and the mean plane through the hydrazono-3-oxobutanoate unit is 2.69 (3)°. An intra-molecular N - H?O hydrogen bond generates an S(6) ring motif. In the crystal packing, C - H?O(3-oxo) inter-actions link mol-ecules into dimers. The dimers thus formed are linked through C - H?O(carboxyl-ate C=O) inter-actions, leading to the formation of ribbons along the [01 ] direction, which are stabilized via Cl?Cl [3.2916 (3) Å] contacts. The ribbons are stacked via C?O contacts [3.2367 (12)-3.3948 (12) Å].