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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.

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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).

| S-EPMC4719945 | biostudies-literature

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. π-π 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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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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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].

| S-EPMC3589019 | biostudies-literature

3-tert-Butyl-4-oxo-3,4-dihydro-phthalazin-1-yl 3,5-dimethyl-benzoate.

Project description:The title compound, C(21)H(22)N(2)O(3), was synthesized by the reaction of tert-butyl-hydrazine with phthalic anhydride and further O-benzoyl-ation of the resulting inter-mediate by 3,5-dimethyl-benzoyl chloride. Inter-molecular C-H?O=C inter-actions link the mol-ecules into layers.

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Di-n-butyl-ammonium 2-[(3,5-di-tert-butyl-4-hy-droxy-benz-yl)sulfan-yl]benzoate.

Project description:The title salt, C(8)H(20)N(+)·C(22)H(27)O(3)S(-), is a proton-transfer compound derived from the recently reported parent carb-oxy-lic acid [Alhadi et al. (2010). Acta Cryst. E66, o1787] by the addition of a second equivalent of di-n-butyl-amine, yielding the di-n-butyl-ammonium carboxyl-ate salt. The structure of the carboxyl-ate anion resembles that of the parent carb-oxy-lic acid. The main difference lies in the position of the H atom in the 4-hy-droxy group. In the anion the O-H bond is perpendicular, rather than parallel, to the benzyl ring. This position appears to facilitate hydrogen bonding to an O atom of the carboxyl-ate group of a symmetry-related anion. In addition, there are three N-H⋯O hydrogen bonds. In contrast, the neutral species hydrogen bonds via a carboxylic acid dimer. The dihedral angle between the benzene rings in the anion is 79.19 (7)°.

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Ethyl 4-[(3,5-di-tert-butyl-2-hy-droxy-benz-yl)amino]-benzoate.

Project description:The title amine, C(24)H(33)NO(3), has two substituted aromatic rings at either end of the -CH(2)NH- linkage [C(ar-yl)-CH(2)-NH-C(ar-yl) torsion angle = 77.4 (3)°]. The amino and hy-droxy groups are hydrogen-bond donors to the carbonyl O atom of an adjacent mol-ecule. These hydrogen bonds give rise to a chain that runs along the b axis. One of the tert-butyl groups is disordered over two positions with a site-occupation factor of 0.834 (6) for the major occupied site.

| S-EPMC3009098 | biostudies-literature

Crystal structure of 2-oxo-2<i>H</i>-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 π-π 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⋯π 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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