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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.

ABSTRACT: 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 ?-? [centroid-centroid separation = 3.960?(2)?Å] inter-actions, which link the dimers into a three-dimensional network.

SUBMITTER: Raja R

PROVIDER: S-EPMC4555410 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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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.

Raja Rajamani R Kandhasamy Subramani S Perumal Paramasivam T PT SubbiahPandi A A

Acta crystallographica. Section E, Crystallographic communications 20150806 Pt 9

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 0.5 ...[more]

PMID: 26396884

Similar Datasets

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

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

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

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

Project description: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.

| S-EPMC4350753 | biostudies-literature

3-[(4-Oxo-4H-thio-chromen-3-yl)meth-yl]-4H-thio-chromen-4-one.

Project description:The title mol-ecule, C19H12S2O2, lies on a twofold rotation axis. The thio-chromonone unit is essentially planar, with a maximum deviation of 0.0491?(14)?Å. The dihedral angle between the thio-chromenone ring systems is 64.48?(4)°. In the crystal, there are weak ?-? stacking inter-actions, with a centroid-centroid distance of 3.7147?(9)?Å.

| S-EPMC3588462 | biostudies-literature

3'-[Hy-droxy(4-oxo-4H-chromen-3-yl)meth-yl]-2-oxospiro-[indoline-3,2'-pyrrolidine]-3'-carbonitrile.

Project description:In the title compound, C(23)H(19)N(3)O(4), the pyran ring adopts a half-chair conformation, while the pyrrolidine (with a C atom as the flap atom) and the five-membered ring in the indoline (with a C atom as the flap atom) ring system adopt slight envelope conformations. The pyrrolidine ring makes dihedral angles of 83.3?(1) and 60.4?(1)° with the mean plane through all non-H atoms of the indoline and chromene ring systems, respectively. In the crystal, mol-ecules are connected by two unique N-H?O and O-H?O hydrogen-bonding inter-actions, which form centrosymmetric patterns described by graph-set motifs R(2) (2)(18) and R(2) (2)(14). These two motifs combine to form a hydrogen-bonded chain which propagates in the a-axis direction. The crystal structure is also stablized by C-H?O inter-actions and by aromatic ?-? stacking inter-actions between the pyran and benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.755?(1)?Å and slippage = 1.371?(2)?Å].

| S-EPMC3254481 | biostudies-literature

Methyl 3'-(2,5-di-methyl-benz-yl)-1'-methyl-2-oxo-4'-phenyl-spiro-[indoline-3,2'-pyrrolidine]-3'-carboxyl-ate chloro-form monosolvate.

Project description:In the title solvate, C29H30N2O3·CHCl3, the dihedral angle between the indole ring system (r.m.s. deviation = 0.050 Å) and the 4-methyl-pyrrolidine ring is 88.88 (8)°. The latter ring adopts an envelope conformation with the N atom as the flap. Its mean plane makes dihedral angles of 86.94 (11) and 42.08 (9)° with the phenyl and di-methyl-benzene rings, respectively. The mol-ecular conformation is stabilized by intra-molecular C-H⋯O hydrogen bonds, which generate S(6) and S(9) ring motifs. The chloro-form solvent mol-ecule is linked to the organic mol-ecule by a C-H⋯O hydrogen bond involving the carbonyl O atom of the carboxyl-ate group. In the crystal, mol-ecules are linked via bifurcated N-H⋯(N,O) and C-H⋯O hydrogen bonds, forming chains propagating along [001].

| S-EPMC3998463 | biostudies-literature

3-(6-Bromo-4-oxo-4H-chromen-3-yl)-3,4-dihydro-2H-1,2,4-benzothia-diazine-1,1-dione.

Project description:The mol-ecular structure of the title compound, C(16)H(11)BrN(2)O(4)S, is very similar to that of the previously reported fluoro analogue [al-Rashida et al. (2010 ?). Acta Cryst. E66, o2707]. The mean planes of the bicyclic chromone system and the benzene ring of the benzothia-diazine derivative make a dihedral angle of 58.23?(8)°. An intra-molecular N-H?O hydrogen bond occurs. In the crystal, mol-ecules are linked into layers by N-H?O and C-H?O hydrogen bonds, generating an infinite two-dimensional network.

| S-EPMC3011492 | 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

6-Chloro-8-nitro-4-oxo-4H-chromene-3-carbaldehyde.

Project description:In the title compound, C10H4ClNO5, the non-H atoms of the 6-chloro-chromone unit are coplanar (r.m.s. deviation = 0.017?Å) with the largest deviation from the mean plane [0.031?(2)?Å] being found for the C=O C atom. The nitro group (NO2) is inclined to the chromone unit mean plane by 13.3?(2) °. The formyl group is also twisted with respect to the attached ring [C-C-C-O torsion angles = 10.8?(4) and -171.8?(2)°]. In the crystal, mol-ecules are linked via C-H?O hydrogen bonds forming slab-like networks lying parallel to (-301). The slabs are linked by ?-? inter-actions involving the benzene rings of the chromone units [centroid-centroid distance = 3.770?(3)?Å].

| S-EPMC4011269 | biostudies-other

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