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2-Oxo-2H-chromen-7-yl 4-tert-butyl-benzoate.

ABSTRACT: In the title compound, C20H18O4, the benzoate ring is oriented at an acute angle of 33.10 (12)° with respect to the planar (r.m.s deviation = 0.016 Å) coumarin ring system. An intra-molecular C-H⋯O hydrogen bond closes an S(6) ring motif. In the crystal, C-H⋯O contacts generate infinite C(6) chains along the b-axis direction. Also present are π-π stacking inter-actions between neighbouring pyrone and benzene rings [centroid-centroid distance = 3.7034 (18) Å] and C=O⋯π inter-actions [O⋯centroid = 3.760 (3) Å]. The data obtained from quantum chemical calculations performed on the title compound are in good agreement with the observed structure, although the calculated C-O-C-C torsion angle between the coumarin ring system and the benzoate ring (129.1°) is somewhat lower than the observed value [141.3 (3)°]. Hirshfeld surface analysis has been used to confirm and qu-antify the supra-molecular inter-actions.

SUBMITTER: Ouedraogo M

PROVIDER: S-EPMC5946982 | biostudies-literature |

REPOSITORIES: biostudies-literature

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2-Oxo-2H-chromen-4-yl 4-tert-butyl-benzoate.

Project description:In the title mol-ecule, C(20)H(18)O(4), the three methyl groups of the tert-butyl substituent show rotational disorder. Each methyl group is split over three positions, with refined site-occupation factors of 0.711?(4), 0.146?(3) and 0.144?(4). The benzene ring of the benzoate group is oriented at a dihedral angle of 60.70?(7)° with respect to the planar chromene ring [maximum deviation = 0.046?(2)?Å]. The crystal structure features centrosymmetric R(2) (2)(8) dimers formed via C-H?O inter-actions, and these dimeric aggregates are connected by C-H?? inter-actions.

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2-Oxo-2H-chromen-4-yl 4-methyl-benzoate.

Project description:The asymmetric unit of the title compound, C17H12O4, consists of two independent mol-ecules. The chromen-2-one ring and the 4-methyl-benzoate side chain are inclined to one another at a dihedral angle of 64.79?(10)° in one mol-ecule and 88.3?(1)° in the other. In the crystal, mol-ecules form R 2 (2)(8) centrosymmetric dimers via C-H?O hydrogen bonds. These dimers are stacked by C-H?O hydrogen bonds, resulting in R 2 (2)(18) and R 3 (2)(16) ring motifs. ?-? stacking inter-actions between two parallel chromen-2-one rings, with centroid-centroid distances of 3.743?(1) and 3.771?(1)?Å, are also present.

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Crystal structure of (tert-butyl-carbamo-yl)(4-chloro-2-oxo-2H-chromen-3-yl)methyl acetate.

Project description:In the title compound, C17H18ClNO5, which was synthesized by reacting 4-chloro-3-formyl-coumarin, acetic acid and tert-butyl isocyanide, the acetamido side chain is convoluted with ring-to-side chain C-C-C-C, C-C-C-N and C-C-N-C torsion angles of -123.30?(14), -135.73?(12) and 176.10?(12)°, respectively. In the crystal, N-H?O and weak C-H?O hydrogen bonds are present, which together with ?-? coumarin-ring inter-actions [ring centroid separations = 3.4582?(8) and 3.6421?(9)?Å], give rise to a layered structure lying parallel to (001).

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2-Oxo-2H-chromen-4-yl 4-meth-oxy-benzoate.

Project description:In the title mol-ecule, C17H12O5, the chromen-2-one ring and the 4-meth-oxy-benzoate side chain are inclined to one another at a dihedral angle of 69.82?(9)°. The crystal structure features parallel sheets of centrosymmetric R2(2)(6) dimers joined by a C(7) chain, resulting in centrosymetric tetra-mers of hydrogen-bonded mol-ecules with graph-set motif R4(4)(40). These centrosymetric tetra-mers are connected by a pair of hydrogen bonds described by an R2(2)(8) ring motif and a C(7) chain via C-H?O inter-actions. In the structure, there are also ?-? stacking inter-actions between chromene benzene and the six-membered heterocyclic rings [centroid-centroid distance = 3.691?(2)?Å] and weak C=O?? inter-actions [O?(ring centroid) distance = 3.357?(3)?Å].

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Crystal structure of 2-oxo-2H-chromen-7-yl 4-fluoro-benzoate.

Project description:In the title compound, C16H9FO4, (I), the benzene ring is oriented at an acute angle of 59.03?(15)° relative to the coumarin plane (r.m.s deviation = 0.009?Å). This conformation of (I) is stabilized by an intra-molecular C-H?O hydrogen bond, which closes a five-membering ring. In the crystal, mol-ecules of (I) form infinite zigzag chains along the b-axis direction, linked by C-H?O hydrogen bonds. Furthermore, the crystal structure is supported by ?-? stacking inter-actions between neighbouring pyrone and benzene or coumarin rings [centroid-centroid distances in the range 3.5758?(18)-3.6115?(16)?Å], as well as C=O?? inter-actions [O?centroid distances in the range 3.266?(3)-3.567?(3)?Å]. The theoretical data for (I) obtained from quantum chemical calculations are in good agreement with the observed structure, although the calculated C-O-C-C torsion angle between the coumarin fragment and the benzene ring (73.7°) is somewhat larger than the experimental value [63.4?(4)°]. Hirshfeld surface analysis has been used to confirm and qu-antify the supra-molecular inter-actions.

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4-Hy-droxy-3-[(4-hy-droxy-6,7-dimethyl-2-oxo-2H-chromen-3-yl)(4-oxo-4H-chromen-3-yl)meth-yl]-6,7-dimethyl-2H-chromen-2-one.

Project description:In the title compound, C(32)H(24)O(8), the mol-ecular structure is disordered over two positions with refined site occupancies of 0.8746?(10) and 0.1254?(10). The mean plane of the three chromeno rings make dihedral angles with each other of 65.12?(4), 62.91?(4) and 59.70?(4)° in the major occupancy component and 59.1?(3), 66.1?(3) and 58.8?(3)° in the minor component. Intra-molecular O-H?O hydrogen bonds stabil-ize the mol-ecular structure and the crystal structure is stabilized by weak C-H?? and ?-? inter-actions [centroid-centroid distances 3.496?(6)-3.672?(7)?Å].

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3-tert-Butyl-2-oxo-1-oxaspiro-[4.5]dec-3-en-4-yl 4-chloro-benzoate.

Project description:The title tetronic acid derivative, C(20)H(23)ClO(4), which is a spiro-diclofen analogue, has two crystallographically independent mol-ecules in the asymmetric unit (Z' = 2). The cyclo-hexane rings in the respective mol-ecules A and B adopt chair conformations [four C atoms are planar with mean deviations of 0.013?(2) and 0.001?(2)?Å, and the flap positions deviate by 0.653?(4) and -0.663?(3)?Å (mol-ecule A) and 0.642?(4) and -0.643?(5)?Å (mol-ecule B) from the plane]. The furan ring makes dihedral angles of 86.9?(1) (mol-ecule A) and 85.4?(1)° (mol-ecule B) with the respective benzene rings.

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Ethyl 2-[N-(tert-butyl-sulfin-yl)carbamo-yl]benzoate.

Project description:The title compound, C(14)H(19)NO(4)S, was obtained in quanti-tative yield by Lewis acid-catalysed alcoholysis of a phtalimide precursor. An intra-molecular C-H⋯O hydrogen bond occurs. In the crystal, centrosymmetric dimers are formed by pairs of N-H⋯O hydrogen bonds between the sulfinyl O atoms and the carbamoyl N-H group of a neighboring mol-ecule. C-H⋯O inter-actions feature in the crystal structure.

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6,8-Di-tert-butyl-3-(4-nitro-phen-yl)-2H-chromen-2-one.

Project description:The title compound, C(23)H(25)NO(4), was synthesized by the reaction of 2-(4-nitro-phen-yl)acetonitrile and 3,5-di-tert-butyl-2-hydroxy-benzaldehyde. The dihedral angle formed by the benzene ring and the mean plane through the benzopyran-one ring system is 35.57?(5)°. The nitro group is almost coplanar with the attached benzene ring [dihedral angle = 5.19?(15)°]. The crystal packing is stabilized by an inter-molecular C-H?O hydrogen-bond inter-action.

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Crystal structure of 3,4-dimethyl 2-(tert-butyl-amino)-5-[2-oxo-4-(thio-morpholin-4-yl)-2H-chromen-3-yl]furan-3,4-di-carboxyl-ate ethyl acetate hemisolvate.

Project description:In the title hemisolvate, C25H28N2O7S·0.5C4H8O2, the thio-morpholine ring adopts a chair conformation, with the exocyclic N-C bond in an equatorial orientation. The dihedral angle between the coumarin ring system (r.m.s. deviation = 0.044 Å) and the furan ring is 64.84 (6)°. An intra-molecular N-H⋯O hydrogen bond closes an S(6) ring. The ethyl acetate solvent mol-ecule is disordered about a crystallographic inversion centre. In the crystal, the components are linked by C-H⋯O and C-H⋯S hydrogen bonds, generating a three-dimensional network.

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