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4,8-Dimethyl-pyrano[2,3-a]carbazol-2(11H)-one.

ABSTRACT: The mol-ecule of the title compound, C(17)H(13)NO(2), is nearly planar, the r.m.s. deviation for all non-H atoms excluding the two methyl C atoms being 0.089 Å. Inter-molecular N-H⋯O and C-H⋯O hydrogen bonds are found in the crystal structure. C-H⋯π inter-actions are also found. The H atoms of the methyl group attached to the benzene ring are disordered equally over two positions.

SUBMITTER: Sridharan M

PROVIDER: S-EPMC2968986 | biostudies-literature |

REPOSITORIES: biostudies-literature

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2,2-Dimethyl-2,3-dihydro-pyrano[2,3-a]carbazol-4(11H)-one.

Project description:The title compound, C(17)H(15)NO(2), was prepared from 1-hydroxy-carbazole and 3,3-dimethyl-acrylic acid with a mixture of AlCl(3) and POCl(3) as the cyclization catalyst. Owing to the presence of the -CMe(2)- group, the mol-ecule is not quite planar. In the crystal structre, strong N-H⋯O hydrogen bonds and weaker C-H⋯π inter-actions occur, and a slipped π-π stacking inter-action [centroid-centroid separation = 3.8425 (8) Å] is also observed.

| S-EPMC2959512 | biostudies-literature

2,2,10-Trimethyl-2,3-dihydro-pyrano[2,3-a]carbazol-4(11H)-one.

Project description:The title compound, C(18)H(17)NO(2), was prepared from 1-hydr-oxy-8-methyl-carbazole and 3,3-dimethyl-acrylic acid with trifluoro-acetic acid as the cyclization catalyst. Due to the -CMe(2)- group, the mol-ecule is not quite planar. The packing is dominated by the strong N-H⋯O hydrogen bonds and some weaker C-H⋯O and C-H⋯π inter-actions. π-π Stacking inter-actions [centroid-centroid separation = 3.806 (2) Å] join neighboring mol-ecules into loosely connected inversion dimers.

| S-EPMC2959518 | biostudies-literature

2,2,9-Trimethyl-2,3-dihydro-pyrano[2,3-a]carbazol-4-(11H)-one.

Project description:The title compound, C(18)H(17)NO(2), was prepared from 1-hydr-oxy-7-methyl-carbazole and 3,3-dimethyl-acrylic acid with trifluoro-acetic acid as the cyclization catalyst. The mol-ecules contain an essentially planar 6-methyl-indole unit. The second aromatic ring is significantly bent away from the plane of this unit, with maximum deviations of 0.171 (1) and 0.185 (1) Å for two of the C atoms. In the crystal structure, there are neither N-H⋯O hydrogen bonds nor π-π stacking between the aromatic sections of neighboring mol-ecules. There is only one weak C-H⋯O hydrogen bond and a number of weak C-H⋯π inter-actions.

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3,4-Dimethyl-pyrano[2,3-c]pyrazol-6(2H)-one.

Project description:The asymmetric unit of the title compound, C(8)H(8)N(2)O(2), comprises two independent mol-ecules in both of which, all non-H atoms lie in a common plane (r.m.s. deviation = 0.014 and 0.017?Å). In the crystal, N-H?O hydrogen bonds connect the mol-ecules into zigzag chains running along [10-1]. Weak C-H?O inter-actions connect the chains into an infinite network.

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3,4-Dimethyl-1-phenyl-pyrano[2,3-c]pyrazol-6(1H)-one.

Project description:In the title compound, C(14)H(12)N(2)O(2), the dihedral angle between the phenyl ring and the 3,4-dimethyl-pyrano[2,3-c]pyrazol-6(1H)-one system is 7.28?(6)°. An intra-molecular C-H?O inter-action generates an S(6) ring. In the crystal, the mol-ecules are linked by C-H?O hydrogen bonds, forming C(8) chains. C-H?? and ?-? inter-actions [centroid-centroid separation = 3.6374?(12)?Å] further consolidate the packing.

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Project description:The title compound, C(14)H(12)N(2)O(2), is almost planar with an r.m.s. deviation for all non-H atoms of 0.038?Å. The observed planarity is rationalized in terms of a close intra-molecular C-H?O inter-action. Supra-molecular layers, two mol-ecules thick and with a step topology, are formed in the crystal packing via C-H?O contacts involving the carbonyl O atom, which accepts two such bonds, and ?-? inter-actions between the components of the fused ring system and the phenyl ring of inversion-related mol-ecules [centroid-centroid distances = 3.6819?(13) and 3.6759?(12)?Å].

| S-EPMC3344066 | biostudies-literature

5-Chloro-3,6-dimethyl-1-phenyl-1H,4H-pyrano[2,3-c]pyrazol-4-one.

Project description:In the title compound, C(14)H(11)ClN(2)O(2), two independent mol-ecules (A and B) comprise the asymmetric unit with the main difference between them being the relative orientation of the pendent phenyl ring with respect to the fused-ring system [dihedral angles = 8.32?(8)° (A) and 28.32?(8)° (B)]. In the crystal, the A mol-ecules are connected into a linear supra-molecular chain along the a axis via C-H?O inter-actions and linked to this via C-H?Cl inter-actions are the B mol-ecules. The chains are connected into layers in the ab plane by ?-? inter-actions between pyrazole (A) and pyran (B) rings, and between pyrazole (B) and pyran (A) rings [centroid-centroid distances = 3.5442?(11) and 3.4022?(10)?Å, respectively].

| S-EPMC3394042 | biostudies-literature

4,4-Dimethyl-2-tosyl-1,2,3,3a,4,11b-hexa-hydro-11H-pyrrolo[3,4-c]pyrano[5,6-c]chromen-11-one 0.125-hydrate.

Project description:In the title compound, C(23)H(23)NO(5)S·0.125H(2)O, the pyrrolidine ring has a twist conformation and the dihydro-pyran ring adopts a half-chair conformation; the two rings are cis-fused. The mol-ecule adopts a folded conformation. The sulfonyl-bound phenyl ring and the pyran ring of the coumarin ring system are stacked over one another, with a centroid-centroid distance of 3.7470?(7)?Å; the dihedral angle between the two rings is 18.93?(2)°. An intra-molecular C-H?O hydrogen bond is observed. The solvent water mol-ecule, lying on a twofold rotation axis, is only partially occupied with an occupancy of 0.125 (relative occupancy with respect to the main molecule) and is involved in O-H?O and C-H?O hydrogen bonding.

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9-Ethyl-2,3-dihydro-9H-carbazol-4(1H)-one.

Project description:In the title compound, C(28)H(30)N(2)O(2), the cyclo-hexene ring system adopts a sofa conformation. The crystal structure is stabilized by C-H⋯O inter-actions between methyl H atoms of the ethyl substituents and the O atoms of carbonyl groups of adjacent mol-ecules, and by an inter-molecular carbon-yl-carbonyl inter-actions [3.207 (2) Å].

| S-EPMC2960498 | biostudies-literature

1-[2,6-Dichloro-4-(trifluoro-meth-yl)phen-yl]-3,4-dimethyl-pyrano[2,3-c]pyrazol-6(1H)-one.

Project description:In the title compound, C(15)H(9)Cl(2)F(3)N(2)O(2), the 1,6-dihydro-pyrano[2,3-c]pyrazole ring system is almost planar, with a maximum deviation of 0.0226?(14)?Å, and forms a dihedral angle of 69.90?(6)° with the benzene ring. In the crystal, mol-ecules are linked into a helical chain along the c axis by C-H?O hydrogen bonds.

| S-EPMC3414285 | biostudies-literature

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