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Methyl 7-chloro-2-ethyl-sulfanyl-6-fluoro-4-oxo-4H-thio-chromene-3-carboxyl-ate.

ABSTRACT: In the title compound, C(13)H(10)ClFO(3)S(2), the two-ring system is essentially planar, the mean plane of the benzene ring being inclined at 6.0?(2)° to the plane of the remaining four atoms. The ethyl-sulfanyl group is almost coplanar with the two rings [dihedral angle = 6.4?(2)°], while the carboxyl-ate group is almost perpendicular to it [dihedral angle = 72.4?(2)°]. In the crystal structure, inter-molecular C-H?O and C-H?F hydrogen bonds link the mol-ecules in a stacked arrangement along the a axis.

SUBMITTER: Li Y

PROVIDER: S-EPMC2983649 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

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Methyl 7-chloro-2-ethyl-sulfanyl-6-fluoro-4-oxo-4H-thio-chromene-3-carboxyl-ate.

Li Yang Y Xiao Tao T Liu Dong-Liang DL Yu Guang-Yan GY

Acta crystallographica. Section E, Structure reports online 20100227 Pt 3

In the title compound, C(13)H(10)ClFO(3)S(2), the two-ring system is essentially planar, the mean plane of the benzene ring being inclined at 6.0 (2)° to the plane of the remaining four atoms. The ethyl-sulfanyl group is almost coplanar with the two rings [dihedral angle = 6.4 (2)°], while the carboxyl-ate group is almost perpendicular to it [dihedral angle = 72.4 (2)°]. In the crystal structure, inter-molecular C-H⋯O and C-H⋯F hydrogen bonds link the mol-ecules in a stacked arrangement along th ...[more]

PMID: 21580435

Similar Datasets

Crystal structures of ethyl 6-(4-methyl-phen-yl)-4-oxo-4H-chromene-2-carboxyl-ate and ethyl 6-(4-fluoro-phen-yl)-4-oxo-4H-chromene-2-carboxyl-ate.

Project description:The crystal structures of two chromone derivatives, viz. ethyl 6-(4-methyl-phen-yl)-4-oxo-4H-chromene-2-carboxyl-ate, C19H16O4, (1), and ethyl 6-(4-fluoro-phen-yl)-4-oxo-4H-chromene-2-carboxyl-ate C18H13FO4, (2), have been determined: (1) crystallizes with two mol-ecules in the asymmetric unit. A comparison of the dihedral angles beween the mean planes of the central chromone core with those of the substituents, an ethyl ester moiety at the 2-position and a para-substituted phenyl ring at the 6-position shows that each mol-ecule differs significantly from the others, even the two independent mol-ecules (a and b) of (1). In all three mol-ecules, the carbonyl groups of the chromone and the carboxyl-ate are trans-related. The supra-molecular structure of (1) involves only weak C-H?? inter-actions between H atoms of the substituent phenyl group and the phenyl group, which link mol-ecules into a chain of alternating mol-ecules a and b, and weak ?-? stacking inter-actions between the chromone units. The packing in (2) involves C-H?O inter-actions, which form a network of two inter-secting ladders involving the carbonyl atom of the carboxyl-ate group as the acceptor for H atoms at the 7-position of the chromone ring and from an ortho-H atom of the exocyclic benzene ring. The carbonyl atom of the chromone acts as an acceptor from a meta-H atom of the exocyclic benzene ring. ?-? inter-actions stack the mol-ecules by unit translation along the a axis.

| S-EPMC4704759 | biostudies-literature

6-Chloro-7-fluoro-4-oxo-4H-chromene-3-carbaldehyde.

Project description:In the title compound, C10H4ClFO3, a chlorinated and fluorinated 3-formyl-chromone derivative, all atoms are essentially coplanar (r.m.s. = 0.0336?Å for the non-H atoms), with the largest deviation from the least-squares plane [0.062?(2)?Å] being for a benzene-ring C atom. In the crystal, mol-ecules are linked through stacking inter-actions [centroid-centroid distance between the benzene and pyran rings = 3.958?(3)?Å and inter-planar distance = 3.259?(3)?Å], C-H?O hydrogen bonds, and short C?O contacts [2.879?(3)?Å]. Unsymmetrical halogen-halogen inter-actions between the Cl and F atoms [Cl?F = 3.049?(3)?Å, C-Cl?F = 148.10?(9)° and C-F?Cl = 162.06?(13)°] are also formed, giving a meandering two-dimensional network along the a axis.

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Ethyl 2-amino-4-(3-chloro-phen-yl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carboxyl-ate.

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Ethyl 5-hy-droxy-6-oxo-4-phenyl-5,6-dihydro-4H-cyclo-penta-[b]thio-phene-5-carboxyl-ate.

Project description:In the title mol-ecule, C(16)H(14)O(4)S, the dihydro-cyclo-penta-thio-phenone ring system is almost planar, with an r.m.s. deviation of 0.060?Å from the best fit plane through all nine non-H atoms. The cyclo-penta-none ring adopts a severely flattened envelope conformation with the C atom carrying the OH and ethylcarboxylate substituents at the flap. This atom lies only 0.185?(3)?Å from the plane through the other four C atoms. The phenyl substituent is inclined at 43.37?(5)° to the dihydro-cyclo-penta-thio-phenone mean plane. In the crystal, mol-ecules are linked by pairs of O-H?O hydrogen bonds, forming inversion dimers with R(2) (2)(10) ring motifs. Weak C-H?O hydrogen bonds also link mol-ecules into chains along c, while an approximately orthogonal set of C-H?O contacts form chains along b, resulting in layers lying parallel to (100). Inversion dimers also form through weaker R(2) (2)(12) C-H?S contacts, which combine with C-H?O contacts to form stacks along b.

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Ethyl 7-chloro-1-cyclo-propyl-6-fluoro-8-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxyl-ate.

Project description:In the title compound, C(15)H(12)ClFN(2)O(5), mol-ecules are packed in the crystal lattice in a parallel fashion sustained by various C-H⋯O [C⋯O = 3.065 (5)-3.537 (5) Å] and C-H⋯Cl [3.431 (5)-3.735 (4) Å] inter-actions.

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Ethyl 2-amino-4-(4-methyl-1,3-thia-zol-5-yl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxyl-ate.

Project description:There are two independent mol-ecules in the asymmetric unit of the title compound, C19H16N2O5S, in which the thia-zole rings make dihedral angles of 80.89?(11) and 84.81?(11)° with the pyrano[3,2-c]chromene ring systems. An intra-molecular N-H?O hydrogen bond involving the amino group occurs in each independent mol-ecule. In the crystal, the amino groups are involved in N-H?O and N-H?N hydrogen bonds.

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

Project description:In the title compound, C10H5ClO3, a chlorinated 3-formyl-chromone derivative, all atoms are essentially coplanar (r.m.s. deviation = 0.032?Å for the non-H atoms), with the largest deviation from the least-squares plane [0.0598?(14)?Å] being for a pyran-ring C atom. In the crystal, mol-ecules are linked through stacking inter-actions along the b axis [shortest centroid-centroid distance between the pyran and benzene rings = 3.566?(2)?Å].

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7-Chloro-4-oxo-4H-chromene-3-carbaldehyde.

Project description:In the title compound, C10H5ClO3, a chlorinated 3-formyl-chromone derivative, all atoms are essentially coplanar (r.m.s. deviation = 0.0592?Å for all non-H atoms), with the largest deviation from the least-squares plane [0.1792?(19)?Å] being for the chromone-ring carbonyl O atom. In the crystal, mol-ecules are linked through C-H?O hydrogen bonds to form tetrads, which are assembled by stacking inter-actions [centroid-centroid distance between the pyran rings = 3.823?(3)?Å] and van der Waals contacts between the Cl atoms [Cl?Cl = 3.4483?(16)?Å and C-Cl?Cl = 171.73?(7)°] into a three-dimensional architecture.

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