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Crystal structure of 2-methyl-amino-3-nitro-4-p-tolyl-pyrano[3,2-c]chromen-5(4H)-one.

ABSTRACT: In the racemic title compound, C20H16N2O5, the pyran ring adopts a shallow envelope conformation, with the stereogenic C atom displaced from the other atoms by 0.273?(2)?Å. The dihedral angle between the fused-ring system and the pendant p-tolyl group is 87.62?(7)°. The mol-ecular conformation is consolidated by an intra-molecular N-H?O hydrogen bond, which generates an S(6) ring. In the crystal, mol-ecules are linked by C-H?O inter-actions, resulting in [010] chains.

SUBMITTER: Govindaraj J

PROVIDER: S-EPMC4350753 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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Crystal structure of 2-methyl-amino-4-(6-methyl-4-oxo-4H-chromen-3-yl)-3-nitro-pyrano[3,2-c]chromen-5(4H)-one with an unknown solvate.

Project description:In the title compound, C23H16N2O7, the mean planes of the two chromene units (r.m.s. deviations = 0.031 and 0.064 Å) are almost normal to one another with a dihedral angle of 85.59 (6)°. The central six-membered pyran ring has a distorted envelope conformation, with the methine C atom at the flap. There is an intra-molecular N-H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(12) ring motif. The dimers are linked by pairs of C-H⋯O hydrogen bonds, enclosing R 2 (2)(6) ring motifs, forming zigzag chains along [001]. The chains are linked by a second pair of C-H⋯O hydrogen bonds, forming slabs parallel to (110). Within the slabs there are C-H⋯π inter-actions present. A region of disordered electron density was treated with the SQUEEZE procedure in PLATON [Spek (2015 ▸). Acta Cryst. C71, 9-18] following unsuccessful attempts to model it as plausible solvent mol-ecule(s). The given chemical formula and other crystal data do not take into account the unknown solvent mol-ecule(s).

| S-EPMC4555399 | biostudies-literature

Crystal structure of 4-(6-bromo-4-oxo-4H-chromen-3-yl)-2-methyl-amino-3-nitro-pyrano[3,2-c]chromen-5(4H)-one chloro-form monosolvate.

Project description:In the title compound, C22H13BrN2O7·CHCl3, the pyran ring adopts a shallow sofa conformation with the C atom bearing the bromo-chromene system as the flap [deviation = 0.291 (3) Å]. The dihedral angle between the pyran fused-ring system (all atoms; r.m.s. deviation = 0.032 Å) and the bromo-chromene ring system (r.m.s. deviation = 0.027 Å) is 87.56 (9)°. An intra-molecular N-H⋯O hydrogen bond closes an S(6) ring. The Cl atoms of the solvent mol-ecule are disordered over two sets of sites in a 0.515 (6):0.485 (6) ratio. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R 2 (2)(12) loops. The packing also features C-H⋯O and very weak π-π [centroid-centroid separation = 3.960 (2) Å] inter-actions, which link the dimers into a three-dimensional network.

| S-EPMC4555410 | biostudies-literature

Crystal structure of 4-(6-chloro-4-oxo-4H-chromen-3-yl)-2-methyl-amino-3-nitro-4H,5H-pyrano[3,2-c]chromen-5-one chloro-form monosolvate.

Project description:In the title compound, C23H14Cl4N2O7, the pyran ring has an envelope conformation with the methine C atom as the flap. The chromene rings are almost planar (r.m.s. deviations of 0.027 and 0.018 Å) and their mean planes are inclined to one another by 85.61 (10)°. The mean planes of the pyran ring and the chromene ring fused to it are inclined to one another by 7.41 (13)°. The mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen bond, generating an S(6) ring motif. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R (2) 2(12) ring motif. The dimers are linked by pairs of C-H⋯O hydrogen bonds, enclosing R (2) 2(18) ring motifs, forming chains along [010]. Within the chains there are C-H⋯π inter-actions. The chains are linked via slipped parallel π-π inter-actions, forming a three-dimensional structure [the shortest inter-centroid distance is 3.7229 (19) Å].

| S-EPMC4518942 | biostudies-literature

(4S*)-2-Methyl-amino-3-nitro-4-(4-nitro-phen-yl)-5,6,7,8-tetra-hydro-4H-chromen-5-one.

Project description:The title compound, C16H15N3O6, is asymmetric with a chiral centre located in the pyran ring and crystallizes as a racemate. The six-membered carbocyclic ring adopts an envelope conformation with the central CH2 C atom as the flap. The amine N atom deviates from the mean plane of the pyran ring by 0.1365?(15)?Å. The nitro-phenyl ring is almost orthogonal to the pyran ring and the mean plane of the six-membered carbocyclic ring, the dihedral angle between their mean planes being 88.30?(7) and 87.61?(8)°, respectively. The mol-ecular structure is stabilized by an intra-molecular N-H?O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol-ecules are linked via C-H?O hydrogen bonds, forming infinite bands lying parallel to (-110) and composed of alternate R 2 (2)(24) and R 2 (4)(12) graph-set ring motifs. The crystal structure is further stabilized by C-H?? inter-actions, forming a three-dimensional structure.

| S-EPMC3884480 | biostudies-literature

4-(2-Bromo-phen-yl)-2-phenyl-pyrano[3,2-c]chromen-5(4H)-one.

Project description:In the title compound, C24H15BrO3, the pyran-ochromenone ring is essentially planar, while the 2-bromo-phenyl group is almost perpendicular to it [85.58?(6)°]. In the crystal, inversion dimers linked by pairs of weak C-H?? bonds occur; there is also a short inter-atomic contact found between the Br and carbonyl O atoms [3.016?(1)?Å].

| S-EPMC3588827 | biostudies-other

7,7-Dimethyl-2-methyl-amino-4-(4-methyl-phenyl)-3-nitro-7,8-di-hydro-4H-chromen-5(6H)-one.

Project description:In the title compound, C19H22N2O4, the six-membered cyclo-hexenone ring of the chromene unit adopts an envelope conformation, with the dimethyl-substituted C atom as the flap, while the pyran ring has a boat conformation. These two mean planes are inclined to one another by 6.65?(13)°·The benzene ring is normal to the 4H-chromene moiety mean plane, making a dihedral angle of 89.18?(5)°. The methyl-amine and nitro groups are slightly twisted from the chromene moiety mean plane, with torsion angles C-N-C-O = 1.70?(18) and O-N-C-C = 0.15?(18)°. The mol-ecular structure is characterized by an intra-molecular N-H?O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol-ecules are linked via pairs of weak C-H?O hydrogen bonds, forming inversion dimers. These dimers are connected by further C-H?O hydrogen bonds, forming sheets lying parallel to (10-1).

| S-EPMC4051056 | biostudies-literature

4-(4-Bromo-phen-yl)-2-methyl-amino-3-nitro-5,6,7,8-tetra-hydro-4H-chromen-5-one.

Project description:In the title compound, C16H15BrN2O4, the six-membered carbocyclic ring of the chromene moiety adopts an envelope conformation with the disordered methyl-ene C atom as the flap. The pyran ring is almost orthogonal to the chloro-phenyl ring, making a dihedral angle of 87.11 (12)°. The amine-group N atom deviates significantly from the pyran ring [0.238 (3) Å]. The mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, which generate C(8) chains running parallel to the b axis. The chains are linked by C-H⋯π inter-actions. The methyl-ene-group C atom of the chromene system that is disordered, along with its attached H atoms and the H atoms on the two adjacent C atoms, has an occupancy ratio of 0.791 (7):0.209 (7).

| S-EPMC3685080 | biostudies-literature

rac-4-(4-Chloro-phen-yl)-2-methyl-amino-3-nitro-5,6,7,8-tetra-hydro-4H-chromen-5-one.

Project description:The title compound, C16H15ClN2O4, contains a chiral centre and crystallizes as a racemate. The methyl-ene group β-positioned to the carbonyl group is partially (21%) disordered. It flips to the opposite sides of the corresponding six-membered carbocycle by -0.304 (3) and 0.197 (11) Å, producing alternative envelope conformations. The planes of the pyran and chloro-phenyl rings form a dihedral angle of 86.25 (9)°. The mol-ecular structure is characterized by an intra-molecular N-H⋯O inter-action, which generates an S(6) ring motif. The corresponding amino N atom deviates from the plane of the pyran ring by 0.1634 (19) Å. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming C(8) chains running parallel to the b-axis direction. The crystal structure also features C-H⋯π inter-actions.

| S-EPMC3772485 | biostudies-literature

Crystal structure of 4-(4-meth-oxy-phen-yl)-7,7-dimethyl-2-methyl-amino-3-nitro-7,8-di-hydro-4H-chromen-5(6H)-one.

Project description:In the title compound, C19H22N2O5, the six-membered carbocyclic ring of the chromene moiety adopts an envelope conformation with the dimethyl-substituted C atom as the flap. The pyran ring has a flat-boat conformation. The meth-oxy-phenyl ring is orthogonal to the mean plane of the chromene moiety, with a dihedral angle of 89.97 (8)°. The amine N atom deviates from the chromene mean plane by 0.1897 (16) Å. The methyl-amine and the nitro group are involved in an intra-molecular N-H⋯O hydrogen bond which generates an S(6) ring motif. They are slightly twisted out of the plane of the chromene moiety with torsion angles of C-N-C-O(pyran) = 2.2 (3)° and O(nitro)-N-C-C = -5.6 (2)°. In the crystal, there are only C-H⋯π inter-actions present, forming inversion-related dimers.

| S-EPMC4186140 | biostudies-literature

3-Methyl-4H-chromen-4-one.

Project description:In the title chromenone derivative, C(10)H(8)O(2), the two fused six-membered rings are coplanar, with a mean deviation of 0.0261 (1) Å from the plane through the non-H atoms of the rings. The carbonyl and methyl substituents of the pyran ring also lie close to that plane, with the O and C atoms deviating by 0.0557 (1) and 0.1405 (1) Å, respectively. In the crystal, weak C-H⋯O contacts form chains along the a axis.

| S-EPMC3007079 | biostudies-literature

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