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Crystal structure, Hirshfeld surface analysis and inter-action energy calculation of 4-(furan-2-yl)-2-(6-methyl-2,4-dioxo-pyran-3-yl-idene)-2,3,4,5-tetra-hydro-1H-1,5-benzodiazepine.

ABSTRACT: The title compound {systematic name: (S,E)-3-[4-(furan-2-yl)-2,3,4,5-tetra-hydro-1H-benzo[b][1,4]diazepin-2-yl-idene]-6-methyl-2H-pyran-2,4(3H)-dione}, C₁₉H₁₆N₂O₄, is constructed from a benzodiazepine ring system linked to furan and pendant di-hydro-pyran rings, where the benzene and furan rings are oriented at a dihedral angle of 48.7 (2)°. The pyran ring is modestly non-planar [largest deviation of 0.029 (4) Å from the least-squares plane] while the tetra-hydro-diazepine ring adopts a boat conformation. The rotational orientation of the pendant di-hydro-pyran ring is partially determined by an intra-molecular N-H_Diazp⋯O_Dhydp (Diazp = diazepine and Dhydp = di-hydro-pyran) hydrogen bond. In the crystal, layers of mol-ecules parallel to the bc plane are formed by N-H_Diazp⋯O_Dhydp hydrogen bonds and slipped π-π stacking inter-actions. The layers are connected by additional slipped π-π stacking inter-actions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (46.8%), H⋯O/O⋯H (23.5%) and H⋯C/C⋯H (15.8%) inter-actions, indicating that van der Waals inter-actions are the dominant forces in the crystal packing. Computational chemistry indicates that in the crystal the N-H⋯O hydrogen-bond energy is 57.5 kJ mol^-1.

SUBMITTER: El Hafi M

PROVIDER: S-EPMC8340973 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Ethyl {4-[(1,5-dimethyl-2,4-dioxo-2,3,4,5-tetra-hydro-1H-1,5-benzo-diazepin-3-yl)meth-yl]-1,2,3-triazol-1-yl}acetate.

Project description:In the title compound, C(18)H(21)N(5)O(4), the diazepine ring adopts a boat conformation with the triazolylmethyl-bearing C atom as the prow and the C atoms at the ring junction as the stern.

| S-EPMC3009227 | biostudies-literature

4-[(1,5-Dibenzyl-2,4-dioxo-2,3,4,5-tetra-hydro-1H-1,5-benzodiazepin-3-yl)meth-yl]-1-n-octyl-1H-1,2,3-triazole.

Project description:The reaction of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione with 1-azido-n-octane in the presence of catalysts leads to the formation of the title compound, C(34)H(39)N(5)O(2), which features a phenyl-ene ring fused with a seven-membered diazepinyl ring. The latter ring adopts a boat conformation with the octyltriazolylmethyl-bearing C atom as the prow and the fused-ring C atoms as the stern. The octyltriazolylmethyl substituent occupies an axial position.

| S-EPMC2980118 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 3,4-dihydro-2-(2,4-dioxo-6-methylpyran-3-ylidene)-4-(4-pyridin-4-yl)-1,5-benzodiazepine.

Project description:The title compound, C20H17N3O3 [systematic name: 2-(6-methyl-2,4-dioxo-pyran-3-yl-idene)-4-(pyridin-4-yl)-2,3,4,5-tetra-hydro-1H-1,5-benzodiazepine], is built up from a benzodiazepine ring system linked to pyridyl and pendant di-hydro-pyran rings, where the benzene and pyridyl rings are oriented at a dihedral angle of 43.36 (6)°. The pendant di-hydro-pyran ring is rotationally disordered in a 90.899 (3):0.101 (3) ratio with the orientation of each component largely determined by intra-molecular N-HDiazp⋯ODhydp (Diazp = diazepine and Dhydp = di-hydro-pyran) hydrogen bonds. In the crystal, mol-ecules are linked via pairs of weak inter-molecular N-HDiazp⋯ODhydp hydrogen bonds, forming inversion-related dimers with R 2 2(26) ring motifs. The dimers are further connected along the b-axis direction by π-π stacking inter-actions between the pendant di-hydro-pyran and pyridyl rings with centroid-centroid distances of 3.833 (3) Å and a dihedral angle of 14.51 (2)°. Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (50.1%), H⋯C/C⋯H (17.7%), H⋯O/O⋯H (16.8%), C⋯C (7.7%) and H⋯N/N⋯H (5.3%) inter-actions. Hydrogen-bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing.

| S-EPMC6323877 | biostudies-literature

Ethyl 2-{4-[(1,5-dibenzyl-2,4-dioxo-2,3,4,5-tetra-hydro-1H-1,5-benzo-diazepin-3-yl)meth-yl]-1H-1,2,3-triazol-1-yl}acetate.

Project description:The reaction of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione with ethyl azido-acetate in the presence of copper sulfate pentahydrate and sodium ascorbate leads to the formation of the title regioisomer, C(30)H(29)N(5)O(4), which features a phenyl-ene ring fused with a seven-membered diazepinyl ring. The latter ring adopts a boat conformation (with the methyl-triazolylacetate-bearing C atom as the prow and the fused-ring C atoms as the stern). The benzyl groups connected to the diazepinyl ring jprotrude from the sides; the methyl-triazolylacetate substituent occupies an axial position.

| S-EPMC2980270 | biostudies-literature

1-(12-Azido-n-dodec-yl)-4-[(1,5-dibenzyl-2,4-dioxo-2,3,4,5-tetra-hydro-1H-1,5-benzodiazepin-3-yl)meth-yl]-1H-1,2,3-triazole.

Project description:The reaction of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione with 1,12-diazido-n-dodecane in the presence of catalysts leads to the formation of the title compound, C(38)H(46)N(8)O(2). The seven-membered diazepinyl ring adopts a boat conformation with the azido-dodecyl-triazolylmethyl-bearing C atom as the prow and the fused-ring C atoms as the stern. The octyltriazolylmethyl substituent occupies an axial position.

| S-EPMC2980277 | biostudies-other

[(2R,3S,5R)-3-Acet-oxy-5-(5-formyl-2,4-dioxo-1,2,3,4-tetra-hydro-pyrimidin-1-yl)-2,3,4,5-tetra-hydro-furan-2-yl]methyl acetate.

Project description:In the two independent but very similar mol-ecules (A and B) of the title compound, C(14)H(16)N(2)O(8), both six-membered pyrimidine rings are nearly planar [maximum deviations = 0.010?(3)?Å in A and 0.028?(3)?Å in B]. The five-membered furan-ose ring in mol-ecule A adopts an envelope conformation, while the same ring in mol-ecule B has a twisted conformation. In the crystal, the A mol-ecules are linked via a pair of inter-molecular N-H?O hydrogen bonds, forming dimers. Each A mol-ecule is further linked to a B mol-ecule via a second N-H?O hydrogen bond. There are also a number of C-H?·O inter-actions present, leading to the formation of a three-dimensional network.

| S-EPMC3247360 | biostudies-literature

3-(12-Bromo-dodec-yl)-1,5-dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione.

Project description:The seven-membered ring in the title compound, C(23)H(35)BrN(2)O(2), adopts a boat-shaped conformation (with the C atoms of the fused-ring as the stern and the methine C atom as the prow). The bromo-dodecyl substituent occupies an equatorial position, with the dodecyl chain exhibiting an extended conformation. Weak inter-molecular C-H?O hydrogen bonding is present in the crystal structure.

| S-EPMC3009360 | biostudies-literature

2,4-Bis(4-fluoro-phen-yl)-2,3-dihydro-1H-1,5-benzodiazepine.

Project description:In the title compound, C(21)H(16)F(2)N(2), the seven-membered 1,4-diazepine ring of the benzodiazepine ring system adopts a distorted-boat conformation. The benzene ring of this system makes dihedral angles of 18.6?(2) and 78.8?(2)° with those of two fluoro-phenyl substituents. In the crystal, inversion dimers linked by two weak C-H?F hydrogen bonds generate R(2) (2)(20) ring motifs. There are also weak N-H?? and C-H?? inter-actions.

| S-EPMC3089231 | biostudies-literature

3-Allyl-1,5-dibenzyl-1,5-benzodiazepine-2,4-dione.

Project description:The title compound, C(26)H(24)N(2)O(2), features a benzene ring fused with a seven-membered diazepine ring; the latter ring adopts a boat conformation (with the allyl-dimethyl-amino-methyl-bearing C atom as the prow and the fused-ring C atoms as the stern).

| S-EPMC2972173 | biostudies-literature

3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-1,5-dimethyl-1,5-benzodiazepine-2,4-dione.

Project description:The title compound, C(21)H(21)N(5)O(2), is a 1,4-dimethyl-1,2,3-triazole having dimethyl-benzodiazepindione and phenyl substituents on each methyl group; the substituents are positioned on opposite sides of the five-membered ring. The seven-membered fused-ring of the larger substituent adopts a boat-shaped conformation (with the methine C atom as the prow).

| S-EPMC2983517 | biostudies-literature

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