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Crystal structure of ethyl (4R)-2-amino-7-hy-droxy-4-phenyl-4H-chromene-3-carboxyl-ate.

ABSTRACT: In the title compound, C18H17NO4, the dihedral angle between the phenyl ring and the fused six-membered ring is 77.65 (4)°. The conformation of the mol-ecule is determined in part by an intra-molecular N-H⋯O hydrogen bond between the amino H atom and the carbonyl O atom, forming an S(6) motif. In the crystal, mol-ecules are linked into N-H⋯O hydrogen-bonded inversion dimers which are then connected into chains along [001], forming a two-dimensional network parallel to (100) via O-H⋯O hydrogen bonds. C-H⋯O interactions further contribute to the crystal stability. The ethyl group is disordered over two sets of sites in a 0.801 (5):0.199 (5) ratio.

SUBMITTER: Mague JT

PROVIDER: S-EPMC4518989 | biostudies-literature |

REPOSITORIES: biostudies-literature

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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

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.

| S-EPMC3201281 | biostudies-literature

Ethyl 1-(2-hy-droxy-eth-yl)-2-phenyl-1H-benzimidazole-5-carboxyl-ate.

Project description:There are two mol-ecules in the asymmetric unit of the title compound, C(18)H(18)N(2)O(3). In each one, the benzimidazole ring system is essentially planar, with maximum deviations of 0.027?(1) and 0.032?(1)Å, and makes dihedral angles of 38.64?(6) and 41.48?(6)°, respectively, with the attached benzene rings. An intra-molecular C-H?O hydrogen bond is observed in each mol-ecule. The two independent mol-ecules are connected into a dimer by two inter-molecular O-H?N hydrogen bonds. In the crystal, mol-ecules form a two-dimensional layers parallel to (012) via weak inter-molecular C-H?O hydrogen bonds. In addition, weak ?-? stacking inter-actions are observed with centroid-centroid distances of 3.5244?(12) and 3.6189?(12)?Å.

| S-EPMC3006730 | biostudies-literature

Ethyl 3-amino-1-phenyl-1H-benzo[f]chromene-2-carboxyl-ate.

Project description:The pyranyl ring of the title compound, C(22)H(19)NO(3), adopts a flattened-boat conformation. The dihedral angle between naphthalene and phenyl rings is 78.3 (1)°The mol-ecule also features an intra-molecular N-H⋯O(carbon-yl) hydrogen bond. Adjacent mol-ecules are linked by an inter-molecular N-H⋯O(carbon-yl) hydrogen bond, forming a zigzag chain that runs along the c axis.

| S-EPMC2969098 | biostudies-literature

Methyl 5-hy-droxy-3-phenyl-1,2-oxazolidine-5-carboxyl-ate.

Project description:In the title compound, C(11)H(13)NO(4), the isoxazolidine ring has an envelope conformation with the O atom as the flap. In the crystal, mol-ecules are liked via N-H?O and bifurcated O-H?(O,N) hydrogen bonds forming chains propagating along [010]. There are also C-H?O inter-actions present.

| S-EPMC3344639 | biostudies-literature

Crystal structure of 2-amino-7-hy-droxy-4-(4-hy-droxy-phen-yl)-4H-chromene-3-carbo-nitrile.

Project description:In the title compound, C16H12N2O3, the chromene ring system is nearly planar [maximum deviation from the mean plane = 0.057?(1)?Å], and is almost perpendicular to the benzene ring, with a dihedral angle of 85.29?(5)°. In the crystal, mol-ecules are linked by classical N-H?O, O-H?O and O-H?N hydrogen bonds, and weak C-H?O hydrogen bonds, forming a three-dimensional supra-molecular network. Furthermore, a weak ?-? stacking inter-action is observed; the centroid-to-centroid distance is 3.7260?(7)?Å.

| S-EPMC4571389 | biostudies-literature

Ethyl 4-benzamido-5-phenyl-4H-1,2,4-triazole-3-carboxyl-ate monohydrate.

Project description:In the title compound, C(18)H(16)N(4)O(3)·H(2)O, the dihedral angles between the triazole ring and the phenyl rings are 84.8?(4) and and 39.8?(4)°. The phenyl rings make a dihedral angle of 84.5?(9)°. In the crystal, the molecules are linked by N-H?O and O-H?N hydrogen bonds. An intra-molecular O?N inter-action also occurs [2.827?(3)?Å].

| S-EPMC3100036 | biostudies-literature

rac-Ethyl 2-hy-droxy-2,7,7-trimethyl-4-(4-nitro-phen-yl)-5-oxo-3,4,5,6,7,8-hexa-hydro-2H-chromene-3-carboxyl-ate.

Project description:The title mol-ecule, C21H25NO7, has four stereogenic centres and crystallized as a racemate. It consists of enanti-omeric pairs with the relative configuration rac-(1R*,2S*,3R*). The cyclo-hexenone ring adopts an envelope conformation; the dimethyl-substituted C atom lies 0.640?(1)?Å out of the mean plane formed by the rest of the ring atoms (r.m.s. deviation = 0.016?Å). The oxacyclo-hexene ring adopts a half-chair conformation, the hy-droxy- and carboxyl-substituted C atoms lying -0.336?(1) and 0.419?(1)?Å, respectively, out of the mean plane formed by the rest of the ring atoms (r.m.s. deviation = 0.002?Å). In the crystal, O-H?O hydrogen bonds link the mol-ecules into a chain along the c-axis direction.

| S-EPMC3588292 | biostudies-literature

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

Project description: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.

| S-EPMC2983649 | biostudies-literature

Crystal structure of 4-bromo-phenyl-2-oxo-2H-chromene-3-carboxyl-ate.

Project description:In the title compound, C16H9BrO4, the coumarin ring system is approximately planar, with an r.m.s deviation of the ten fitted non-H atoms of 0.031 Å, and forms a dihedral angle of 25.85 (10)° with the bromo-benzene ring. The carbonyl atoms are syn. In the crystal, mol-ecules are connected along [001] via C-H⋯O inter-actions, forming C(6) chains. Neighbouring C(6) chains are connected via several π-π inter-actions [range of centroid-centroid distances = 3.7254 (15)-3.7716 (16) Å], leading to sheets propagating in the bc plane.

| S-EPMC4420041 | biostudies-literature

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