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2-Chloro-8-methyl-3-[(pyrimidin-4-yl-oxy)meth-yl]quinoline.

ABSTRACT: In the title compound, C(15)H(12)ClN(3)O, the quinoline ring system is essentially planar, with a maximum deviation of 0.017?(1)?Å. The crystal packing is stabilized by ?-? stacking inter-actions between the quinoline rings of adjacent mol-ecule, with a centroid-centroid distance of 3.5913?(8)?Å. A weak C-H?? contact is also observed between mol-ecules.

SUBMITTER: Khan FN

PROVIDER: S-EPMC2979073 | biostudies-literature | 2010 Apr

REPOSITORIES: biostudies-literature

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2-Chloro-8-methyl-3-[(pyrimidin-4-yl-oxy)meth-yl]quinoline.

Khan F Nawaz FN Roopan S Mohana SM Hathwar Venkatesha R VR Akkurt Mehmet M

Acta crystallographica. Section E, Structure reports online 20100402 Pt 5

In the title compound, C(15)H(12)ClN(3)O, the quinoline ring system is essentially planar, with a maximum deviation of 0.017 (1) Å. The crystal packing is stabilized by π-π stacking inter-actions between the quinoline rings of adjacent mol-ecule, with a centroid-centroid distance of 3.5913 (8) Å. A weak C-H⋯π contact is also observed between mol-ecules. ...[more]

PMID: 21579074

Similar Datasets

Crystal structure of 2-chloro-3-(di-meth-oxy-meth-yl)-6-meth-oxy-quinoline.

Project description:The title compound, C13H14ClNO3, crystallizes with Z' = 2 in the space group Pca21, but a search for possible additional crystallographic symmetry found none. However, the crystal structure exhibits pseudosymmetry as the two independent mol-ecules are related by an approximate but non-crystallographic inversion located close to (0.38, 0.26, 1/2) in the selected asymmetric unit, and the structure exhibits partial inversion twinning. The approximate inversion relationship between the two mol-ecules in the selected asymmetric unit is clearly shown by comparison of the relevant torsion angle in the two mol-ecules; the corresponding torsion angles have similar, although not identical magnitudes but with opposite signs. The mean planes of the quinoline rings in the two independent mol-ecules are almost parallel, with a dihedral angle of only 0.16?(3)° between them, and the mutual orientation of these rings permits significant ?-? stacking inter-actions between them [centroid-centroid distances = 3.7579?(15) and 3.7923?(15)?Å]. In addition, the bimolecular aggregates which are related by translation along [010] are linked by a further ?-? stacking inter-action [centroid-centroid distance = 3.7898?(15)?Å], so forming a ?-stacked chain running parallel to [010]. However, there are no C-H?N hydrogen bonds in the structure nor, despite the number of independent aromatic rings, are there any C-H?? hydrogen bonds; hence there are no direction-specific inter-actions between adjacent ?-stacked chains.

| S-EPMC4420130 | biostudies-literature

2-Chloro-3-[(E)-(hydrazin-1-yl-idene)meth-yl]-6-meth-oxy-quinoline.

Project description:In the title compound, C(11)H(10)ClN(3)O, the quinoline ring system is essentially planar, the r.m.s. deviation for the non-H atoms being 0.014?(2)?Å with a maximum deviation from the mean plane of 0.0206?(14)?Å for the C atom bonded to the -CH-N=NH(2) group. In the crystal, molecules are linked via N-H?O and N-H?N hydrogen bonds, forming zigzag layers parallel to (010).

| S-EPMC3344647 | biostudies-literature

6-Chloro-2-(4-meth-oxy-phen-yl)-4-phenyl-quinoline.

Project description:In the title compound, C22H16ClNO, the quinoline ring system makes dihedral angles of 56.30?(6) and 7.93?(6)°, respectively, with the adjacent phenyl and benzene rings. The dihedral angle between these phenyl and benzene rings is 56.97?(8)°. In the crystal, weak C-H?? and ?-? [centroid-centroid distances of 3.7699?(9) and 3.8390?(9)?Å] inter-actions link the mol-ecules into a layer parallel to the ab plane.

| S-EPMC3884500 | biostudies-literature

N-[(2-Chloro-8-methyl-quinolin-3-yl)meth-yl]-4-meth-oxy-aniline.

Project description:In the title compound, C(18)H(17)ClN(2)O, the quinoline ring system is essentially planar; the r.m.s. deviation for the non-H atoms is 0.04?Å with a maximum deviation from the mean plane of 0.026?(4)?Å for the C atom bonded to the -CH(2)- group. The meth-oxy-substituted benzene ring forms a dihedral angle of 70.22?(4)° with this ring system. The crystal structure can be described as zigzag layers in which the quinoline ring systems are parallel to (011) and molecules are connected via inter-molecular N-H?N hydrogen bonds, forming chains along [100]. The crystal studied was an inversion twin with a 0.86?(5):0.14?(5) domain ratio.

| S-EPMC3009236 | biostudies-literature

Methyl 2-[2-(6-chloro-pyrimidin-4-yl-oxy)phen-yl]-3,3-dimethoxy-propanoate.

Project description:In the title compound, C(16)H(17)ClN(2)O(5), the dihedral angle between the aromatic rings is 77.36?(4)°. An intra-molecular C-H?O inter-action results in the formation of a planar [r.m.s. deviation = 0.103 (2) Å] five-membered ring, which is oriented at a dihedral angle of 4.84?(4)° with respect to the adjacent benzene ring. In the crystal structure, weak intermolecular C-H?? inter-actions are found.

| S-EPMC2970010 | biostudies-literature

4-Chloro-6-meth-oxy-pyrimidin-2-amine.

Project description:The title compound, C5H6ClN3O, is essentially planar with a maximum deviation of 0.0256 (11) Å for all non-H atoms. In the crystal, adjacent mol-ecules are linked by a pair of N-H⋯N hydrogen bonds, forming an inversion dimer with an R2(2)(8) ring motif. The dimers are further linked via N-H⋯O hydrogen bonds into an undulating sheet structure parallel to the bc plane.

| S-EPMC3588926 | biostudies-literature

6-Chloro-3-[5-(3-meth-oxy-8-methyl-4-quinol-yl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-2-methyl-4-phenyl-quinoline.

Project description:In the title compound, C(36)H(29)ClN(4)O, the dihydro-pyrazole ring adopts an envelope conformation. The two quinoline ring systems (r.m.s. deviations = 0.029 and 0.018?Å) are oriented at a dihedral angle of 71.43?(4)°. One of the quinoline rings makes a dihedral angle of 65.40?(7)° with the phenyl substituent. In the crystal, mol-ecules are linked into chains along the b axis by inter-molecular C-H?N hydrogen bonds. In addition, C-H?? and ?-? [centroid-centroid distance = 3.7325?(8)?Å] inter-actions are observed.

| S-EPMC2971305 | biostudies-literature

N-(4-Meth-oxy-phen-yl)-6-methyl-2-phenyl-5-{[4-(tri-fluoro-meth-yl)anilino]meth-yl}pyrimidin-4-amine.

Project description:The title compound, C26H23F3N4O, crystallizes with two symmetry-independent mol-ecules in the asymmetric unit, denoted A and B, which differ mainly in the rotation of the meth-oxy-phenyl ring. The -CF3 group of mol-ecule B is disordered by rotation, with the F atoms split over two sets of sites; the occupancy factor for the major component is 0.853?(4). The dihedral angles between the pyrimidine ring and the attached phenyl, meth-oxy-phenyl and tri-fluoro-methyl-phenyl rings are 8.1?(2), 37.5?(2) and 70.7?(2)°, respectively, in mol-ecule A, and 9.3?(2), 5.3?(2) and 79.7?(2)° in mol-ecule B. An intra-molecular N-H?N hydrogen bond occurs in each mol-ecule. In the crystal, two crystallographically independent mol-ecules associate into a dimer via a pair of N-H?N hydrogen bonds, with a resulting R 2 (2)(12) ring motif and ?-? stacking inter-actions [centroid-centroid distance = 3.517?(4)?Å] between the pyrimidine rings. For the A mol-ecules, there are inter-molecular C-H?O hydrogen bonds between an aryl C atom of meth-oxy-phenyl ring and a meth-oxy O atom of an adjacent mol-ecule. A similar inter-action is lacking in the B mol-ecules.

| S-EPMC3885078 | biostudies-literature

N-(3-Meth-oxy-phen-yl)-4-{4-methyl-2-[(meth-yl)(4-methyl-phen-yl)amino]-1,3-thia-zol-5-yl}pyrimidin-2-amine.

Project description:The asymmetric unit of the title compound, C(23)H(23)N(5)OS, contains two independent mol-ecules. In one mol-ecule, the thia-zole and pyrimidine rings are almost co-planar, making a dihedral angle of 2.48?(8)°. In the other mol-ecule, the corresponding dihedral angle is 12.82?(8)°. The crystal structure is stabilized by weak inter-molecular N-H?N and C-H?O inter-actions that extend along the b axis.

| S-EPMC3051738 | biostudies-literature

2-(4-Bromo-anilino)-6-(4-chloro-phen-yl)-5-meth-oxy-carbonyl-4-methyl-3,6-dihydro-pyrimidin-1-ium chloride.

Project description:In the title molecular salt, C19H18BrClN3O2 (+)·Cl(-), the dihedral angles between the pyrimidine ring and the chlorobenzene and bromobenzene rings are 72.4?(2) and 45.5?(2)°, respectively. The dihedral angle between the chlorobenzene and bromobenzene rings is 27.5?(2)°. The conformation of the mol-ecule is stabilized by an intra-molecular C-H?O inter-action. In the crystal, the anion and cation are linked by an N-H?Cl hydrogen bond. Pairs of weak C-H?O and C-H?Cl hydrogen bonds form inversion dimers. Further N-H?Cl hydrogen bonds form R 2 (1)(6) motifs and link the dimers into chains along [101]. Br?Cl short contacts [3.482?(2)?Å] inter-link the hydrogen-bonded chains along the b-axis direction.

| S-EPMC3629576 | biostudies-literature

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