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Crystal structure and Hirshfeld surface analysis of 2-(2-oxo-3-phenyl-1,2,3,8a-tetra-hydro-quinoxalin-1-yl)ethyl acetate.

ABSTRACT: In the title mol-ecule, C₁₈H₁₆N₂O₃, the di-hydro-quinoxaline moiety, with the exception of the N atom is essentially planar with the inner part of the methyl-propano-ate group (CH₂-CH₂-O) nearly perpendicular to it. In the crystal, inversion dimers formed by C-H⋯O hydrogen bonds are connected into oblique stacks by π-stacking and C-H⋯π(ring) inter-actions.

SUBMITTER: Abad N

PROVIDER: S-EPMC8183448 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chloro-benz-yl)-6-oxo-3-phenyl-1,6-di-hydro-pyridazin-1-yl]acetate.

Project description:The title pyridazinone derivative, C21H19ClN2O3, is not planar. The unsubstituted phenyl ring and the pyridazine ring are inclined to each other, making a dihedral angle of 17.41?(13)° whereas the Cl-substituted phenyl ring is nearly orthogonal to the pyridazine ring [88.19?(13)°]. In the crystal, C-H?O hydrogen bonds generate dimers with R 2 2(10) and R 2 2(24) ring motifs which are linked by C-H?O inter-actions, forming chains extending parallel to the c-axis direction. The inter-molecular inter-actions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most significant contributions to the crystal packing are from H?H (44.5%), C?H/H?C (18.5%), H?O/H?O (15.6%), Cl?H/H?Cl (10.6%) and C?C (2.8%) contacts.

| S-EPMC6658951 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of ethyl 2-{4-[(3-methyl-2-oxo-1,2-di-hydro-quinoxalin-1-yl)meth-yl]-1H-1,2,3-triazol-1-yl}acetate.

Project description:The mol-ecule of the title compound, C16H17N5O3, is build up from two fused six-membered rings linked to a 1,2,3-triazole ring, which is attached to an ethyl azido-acetate group. The di-hydro-qinoxalinone portion is planar to within 0.0512?(12)?Å and is oriented at a dihedral angle of 87.83?(5)° with respect to the pendant triazole ring. In the crystal, a combination of inter-molecular C-H?O and C-H?N hydrogen bonds together with slipped ?-stacking [centroid-centroid distance = 3.7772?(12)?Å] and C-H?? (ring) inter-actions lead to the formation of chains extending along the c-axis direction. Additional C-H?O hydrogen bonds link these chains into layers parallel to the bc plane and the layers are tied together by complementary ?-stacking [centroid-centroid distance = 3.5444?(12)?Å] inter-actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H?H (44.5%), H?O/O?H (18.8%), H?N/N?H (17.0%) and H?C/C?H (10.4%) inter-actions.

| S-EPMC6218907 | biostudies-other

Crystal structure, Hirshfeld surface analysis and DFT study of 1-ethyl-3-phenyl-1,2-di-hydro-quinoxalin-2-one.

Project description:In the title mol-ecule, C16H14N2O, the di-hydro-quinoxaline moiety is not planar as there is a dihedral angle of 4.51 (5)° between the constituent rings. In the crystal, C-H⋯O hydrogen bonds form helical chains about the crystallographic 21 screw axis in the b-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (51.7%), H⋯C/C⋯H (26%) and H⋯O/O⋯H (8.5%) inter-actions. The optimized structure calculated using density functional theory (DFT) at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO-LUMO energy gap is 3.8918 eV.

| S-EPMC7784057 | biostudies-literature

rac-(2R,3S)-2-Phenyl-3-(3-phenyl-1,2,3,4-tetra-hydro-quinoxalin-2-yl)quinoxaline.

Project description:The title compound, C(28)H(22)N(4), is the unexpected by-product of the reaction of 2-hydroxy-acetophenone and 1,2-diamino-benzene under iodine catalysis, during which a carbon-carbon ?-bond between two quinoxaline units was formed. Although a fully oxidized title compound should sterically be possible, only one quinoxaline ring is fully oxidized while the second ring remains in the reduced form. As expected, the tetra-hydro-quinoxaline unit is not planar; it adopts a sofa conformation, whereby the atom joining the two heterocyclic systems lies out of the plane of the other atoms. The quinoxaline ring system makes a dihedral angle of 53.61?(4)° with its phenyl ring substituent. The crystal packing is determined by pairs of N-H?N, N-H?? and weak C-H?N hydrogen bonds, forming a chain parallel to the a axis.

| S-EPMC2961777 | biostudies-literature

Ethyl 2-[6-(4-methyl-benzo-yl)-7-phenyl-2,3-di-hydro-1H-pyrrolizin-5-yl]-2-oxo-acetate.

Project description:In the title compound, C25H23NO4, the pyrrolizine ring is approximately planar with an r.m.s deviation from planarity of 0.0053?Å, while the fused di-hydro-pyrrolizine ring adopts an envelope conformation with the C atom connected to two CH2 as the flap. The dihedral angles between the fused ring system and the phenyl and methyl-benzoyl rings are 41.65?(11) and 66.30?(8)°, respectively. In the crystal, weak C-H?O hydrogen bonds and C-H?? inter-actions occur. One mol-ecule is linked to five adjacent ones through eight hydrogen bonds, forming a three-dimensional network.

| S-EPMC3885017 | biostudies-literature

Synthesis and structure of ethyl 2-[(4-oxo-3-phenyl-3,4-di-hydro-quinazolin-2-yl)sulfan-yl]acetate.

Project description:The title compound, C18H16N2O3S, was synthesized by reaction of 2-mercapto-3-phenyl-quinazolin-4(3H)-one with ethyl chloro-acetate. The quinazoline ring forms a dihedral angle of 86.83?(5)° with the phenyl ring. The terminal methyl group is disordered by a rotation of about 60° in a 0.531?(13): 0.469?(13) ratio. In the crystal, C-H?O hydrogen-bonding inter-actions result in the formation of columns running in the [010] direction. Two parallel columns further inter-act by C-H?O hydrogen bonds. The most important contributions to the surface contacts are from H?H (48.4%), C?H/H?C (21.5%) and O?H/H?O (18.7%) inter-actions, as concluded from a Hirshfeld analysis.

| S-EPMC7199254 | biostudies-literature

Crystal structures and Hirshfeld surface analyses of 4-benzyl-6-phenyl-4,5-di-hydro-pyridazin-3(2H)-one and methyl 2-[5-(2,6-di-chloro-benz-yl)-6-oxo-3-phenyl-1,4,5,6-tetra-hydropyridazin-1-yl]acetate.

Project description:The asymmetric units of the title compounds both contain one nonplanar mol-ecule. In 4-benzyl-6-phenyl-4,5-di-hydro-pyridazin-3(2H)-one, C17H14N2O, (I), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 46.69 (9)°; the phenyl ring of the benzyl group is nearly perpendicular to the plane of the pyridazine ring, the dihedral angle being 78.31 (10)°. In methyl 2-[5-(2,6-di-chloro-benz-yl)-6-oxo-3-phenyl-1,4,5,6-tetra-hydropyridazin-1-yl]acetate, C20H16Cl2N2O3, (II), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 21.76 (18)°, whereas the phenyl ring of the di-chloro-benzyl group is inclined to the pyridazine ring by 79.61 (19)°. In the crystal structure of (I), pairs of N-H⋯O hydrogen bonds link the mol-ecules into inversion dimers with an R 2 2(8) ring motif. In the crystal structure of (II), C-H⋯O hydrogen bonds generate dimers with R 1 2(7), R 2 2(16) and R 2 2(18) ring motifs. The Hirshfeld surface analyses of compound (I) suggests that the most significant contributions to the crystal packing are by H⋯H (48.2%), C⋯H/H⋯C (29.9%) and O⋯H/H⋯O (8.9%) contacts. For compound (II), H⋯H (34.4%), C⋯H/H⋯C (21.3%) and O⋯H/H⋯O (16.5%) inter-actions are the most important contributions.

| S-EPMC6829710 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and DFT studies of ethyl 2-{4-[(2-eth-oxy-2-oxoeth-yl)(phen-yl)carbamo-yl]-2-oxo-1,2-di-hydro-quinolin-1-yl}acetate.

Project description:The title com-pound, C24H24N2O6, consists of ethyl 2-(1,2,3,4-tetra-hydro-2-oxo-quinolin-1-yl)acetate and 4-[(2-eth-oxy-2-oxoeth-yl)(phen-yl)carbomoyl] units, where the oxo-quinoline unit is almost planar and the acetate substituent is nearly perpendicular to its mean plane. In the crystal, C-HOxqn?OEthx and C-HPh-yl?OCarbx (Oxqn = oxoquinolin, Ethx = eth-oxy, Phyl = phenyl and Carbx = carboxyl-ate) weak hydrogen bonds link the mol-ecules into a three-dimensional network sturucture. A ?-? inter-action between the constituent rings of the oxo-quinoline unit, with a centroid-centroid distance of 3.675?(1)?Å may further stabilize the structure. Both terminal ethyl groups are disordered over two sets of sites. The ratios of the refined occupanies are 0.821?(8):0.179?(8) and 0.651?(18):0.349?(18). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H?H (53.9%), H?O/O?H (28.5%) and H?C/C?H (11.8%) inter-actions. Weak inter-molecular hydrogen-bond inter-actions and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Density functional theory (DFT) geometric optimized structures at the B3LYP/6-311G(d,p) level are com-pared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO mol-ecular orbital behaviour was elucidated to determine the energy gap.

| S-EPMC6829727 | biostudies-literature

Ethyl 2-(4-benzyl-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl)acetate: crystal structure and Hirshfeld surface analysis.

Project description:The title compound, C16H18N2O3, is constructed about a central oxopyridazinyl ring (r.m.s. deviation = 0.0047?Å), which is connected to an ethyl-acetate group at the N atom closest to the carbonyl group, and benzyl and methyl groups second furthest and furthest from the carbonyl group, respectively. An approximately orthogonal relationship exists between the oxopyridazinyl ring and the best plane through the ethyl-acetate group [dihedral angle = 77.48?(3)°]; the latter lies to one side of the central plane [the Nr-Nr-Cm-Cc (r = ring, m = methyl-ene, c = carbon-yl) torsion angle being 104.34?(9)°]. In the crystal, both H atoms of the N-bound methyl-ene group form methyl-ene-C-H?O(ring carbon-yl) or N(pyridazin-yl) inter-actions, resulting in the formation of a supra-molecular tape along the a-axis direction. The tapes are assembled into a three-dimensional architecture by methyl- and phenyl-C-H?O(ring carbon-yl) and phenyl-C-H?O(ester carbon-yl) inter-actions. The analysis of the calculated Hirshfeld surface indicates the dominance of H?H contacts to the overall surface (i.e. 52.2%). Reflecting other identified points of contact between mol-ecules noted above, O?H/H?O (23.3%), C?H/H?C (14.7%) and N?H/H?N (6.6%) contacts also make significant contributions to the surface.

| S-EPMC6399698 | biostudies-literature

Ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

Project description:The title compound, C(14)H(16)N(2)O(3), belongs to a group of esters of 2-oxo- and 1,2,3,4-tetra-hydro-pyrimidine-5-carboxylic acids, which exhibit a wide spectrum of biological activities. The dihydro-pyrimidine ring adopts a screw-boat conformation. The crystal packing is stabilized by strong N-H?O and weak C-H?O inter-molecular hydrogen bonds. An intra-molecular C-H?O hydrogen bond is also present.

| S-EPMC2960668 | biostudies-literature

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