(6S,7S,8S,8aS)-6-Ethyl-7,8-dihy­droxy-1,5,6,7,8,8a-hexa­hydro­indolizin-3(2H)-one monohydrate

The absolute configuration of the title compound, C10H17NO3·H2O, was assigned from the synthesis. In the mol­ecular structure, the central six-membered ring of the indolizine moiety adopts a chair conformation, with two atoms displaced by −0.578 (2) and 0.651 (1) Å from the plane of the other four atoms [maximum deviation 0.019 (2) Å] The conformation of the fused oxopyrrolidine ring is close to that of a flat envelope, with the flap atom displaced by 0.294 (1) Å from the plane through the remaining four atoms. In the crystal, one of the hy­droxy groups is hydrogen-bonded to two water mol­ecules, while the other hy­droxy group exhibits an inter­molecular hydrogen bond to the carbonyl O atom, resulting in a chain parallel to the b axis

4-Chloro-N-(3,5-dimethyl­phen­yl)benzamide

In the mol­ecular structure of the title compound, C15H14ClNO, the amide group forms dihedral angles of 15.8 (2) and 27.2 (2)°, respectively, with the benzoyl and aniline rings, while the angle between the benzoyl and aniline rings is 11.5 (1)°. The crystal structure is stabilized by N—H⋯O hydrogen bonds, which give rise to infinite chains running along the c axis

(7R,8S,8aS)-8-Hydr­oxy-7-phenyl­perhydro­indolizin-3-one

In the title compound, C14H17NO2, the six-membered ring of the indolizine system adopts a chair conformation. In the crystal, mol­ecules form chains parallel to the b axis via inter­molecular O—H⋯O hydrogen bonds. The absolute mol­ecular configuration was assigned from the synthesis

(8aRS)-8,8a-Dihydro­furo[3,2-f]indolizine-6,9(4H,7H)-dione

The title compound, C10H9NO3, is a chiral mol­ecule with one stereogenic carbon atom, but which crystallizes as a racemate in the centrosymmetric space group P21/n. The central six-membered ring of the indolizine moiety adopts a definite envelope conformation, while the conformation of the oxopyrrolidine ring is close to that of a flat-envelope with a maximum deviation of 0.352 (1) Å for the flap atom

2-Chloro-N-(2,6-dimethyl­phen­yl)benzamide

In the title compound, C15H14ClNO, the dihedral angle between the benzoyl and the aniline rings is 3.30 (18)°. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into chains running along the a axis

2-Chloro-N-(2-methyl­phen­yl)benzamide

In the title compound, C14H12ClNO, the two aromatic rings are almost coplanar, making a dihedral angle of 4.08 (18)°. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into infinite chains running along the a axis

(3aR,8aS,9S,9aR)-9-Hydroxy­perhydro­furo[3,2-f]indolizin-6-one

In the title compound, C10H15NO3, the central six-membered ring of the indolizine system adopts a chair conformation, while the oxopyrrolidine and hydro­furan rings attached to the indolizine ring system have envelope conformations. In the crystal, the mol­ecules form chains parallel to the b axis via inter­molecular O—H⋯O hydrogen bonds. The absolute configuration was assigned from the synthesis

N-(4-Chloro-2-methyl­phen­yl)maleamic acid

In the mol­ecular structure of the title compound, C11H10ClNO3, the conformation of the N—H bond in the amide segment is syn to the ortho-methyl group in the phenyl ring. The C=O and O—H bonds of the acid group are in the relatively rare anti position with respect to each other. This is an obvious consequence of the hydrogen bond donated to the amide carbonyl group. The central oxobutenoic acid core C(=O)—C=C—C—OH is twisted by 31.65 (6)° out of the plane of the 4-chloro-2-methyl­phenyl ring. An intra­molecular O—H⋯O hydrogen bond occurs. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into infinite chains running along the a axis

(7R,8R,8aS)-8-Hydr­oxy-7-phenyl­per­hydro­indolizin-3-one

The absolute configuration of the title compound, C14H17NO2, was assigned from the synthesis. There are two mol­ecules in the asymmetric unit. Their geometries are very similar and corresponding bond lengths are almost identical [mean deviation for all non-H atoms = 0.015 (2) Å]. The six-membered ring of the indolizine system adopts a chair conformation. In the crystal structure, mol­ecules form chains parallel to the a axis via inter­molecular O—H⋯O hydrogen bonds, which help to stabilize the crystal structure