scholarly journals Three 4-(4-fluorophenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in one, two and three dimensions

2020 ◽  
Vol 76 (6) ◽  
pp. 841-847 ◽  
Author(s):  
Chayanna Harish Chinthal ◽  
Hemmige S. Yathirajan ◽  
Sreeramapura D. Archana ◽  
Sabine Foro ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Supramolecular Assembly ◽  
Organic Anions ◽  
Three Dimensions ◽  
Carboxyl Groups ◽  
Rotation Symmetry ◽  
Independent Components ◽  
Multiple Hydrogen Bonds

Three salts containing the 4-(4-fluorophenyl)piperazin-1-ium cation have been prepared and structurally characterized. In 4-(4-fluorophenyl)piperazin-1-ium 2-hydroxy-3,5-dinitrobenzoate, C10H14FN2 +·C7H3N2O7 −, (I), the anion contains an intramolecular O—H...O hydrogen bond, and it has a structure similar to that of the picrate ion. The cations and anions are linked into [001] chains of rings by a combination of two three-centre N—H...(O)2 hydrogen bonds. The anion in 4-(4-fluorophenyl)piperazin-1-ium hydrogen oxalate, C10H14FN2 +·C2HO4 −, (II), is planar, and the cations and anions are linked into (100) sheets by multiple hydrogen bonds including two-centre N—H...O, three-centre N—H...(O)2, O—H...O, C—H...O and C—H...π(arene) types. In 4-(4-fluorophenyl)piperazin-1-ium hydrogen (2R,3R)-tartrate monohydrate, C10H14FN2 +·C4H5O6 −·H2O, (III), the anion exhibits an approximate non-crystallographic twofold rotation symmetry with antiperiplanar carboxyl groups. A combination of eight hydrogen bonds, encompassing two- and three-centre N—H...O systems, O—H...O and C—H...π(arene) types, link the independent components into a three-dimensional framework. Comparisons are made with some related structures.

scholarly journals Fifteen 4-(2-methoxyphenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in zero, one, two and three dimensions

2020 ◽  
Vol 76 (11) ◽  
pp. 1779-1793
Author(s):  
Chayanna Harish Chinthal ◽  
Channappa N. Kavitha ◽  
Hemmige S. Yathirajan ◽  
Sabine Foro ◽  
Ravindranath S. Rathore ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Supramolecular Assembly ◽  
Organic Anions ◽  
Three Dimensions ◽  
Ribbon Structure ◽  
Related Compounds ◽  
Fumarate Salt

Fifteen 4-(2-methoxyphenyl)piperazin-1-ium salts containing organic anions have been prepared and structurally characterized. In the isostructural 4-chlorobenzoate and 4-bromobenzoate salts, C11H17N2O+·C7H4ClO2 − (I) and C11H17N2O+·C7H4BrO2 − (II), and the 4-iodobenzoate salt C11H17N2O+·C7H4IO2 − (III), the ions are linked by N—H...O hydrogen bonds, forming centrosymmetric R 4 4(12) four-ion aggregates; a similar aggregate is formed in the 2-chlorobenzoate salt (V), isomeric with (I). In the 2-fluorobenzoate salt C11H17N2O+·C7H4FO2 − (IV), and the isomorphous pair of salts, the 2-bromobenzoate (VI), isomeric with (II) and 2-iodobenzoate (VII), isomeric with (III), N—H...O and C—H...π(arene) interactions link the components into three-dimensional arrays. Four-ion R 4 4(12) aggregates are also found in the 2-methylbenzoate, 4-aminobenzoate and 4-nitrobenzoate salts, C11H17N2O+·C8H7O2 − (VIII), C11H17N2O+·C7H6NO2 − (IX) and C11H17N2O+·C7H4NO4 − (X), but those in (IX) are linked into complex sheets by an additional N—H...O hydrogen bond. In the 3,5-dinitrobenzoate salt, C11H17N2O+·C7H3N2O6 −·2H2O (XI), N—H...O and O—H...O hydrogen bonds link the components into a complex ribbon structure. In the picrate salt, C11H17N2O+·C6H2N3O7 − (XII), the four-ion aggregates are linked into chains of rings by C—H...O hydrogen bonds. In the hydrogen maleate salt, C11H17N2O+·C4H3O4 − (XIII), two- and three-centre hydrogen bonds link the ions into a ribbon structure while both anions contain very short but asymmetric O—H...O hydrogen bonds, having O...O distances of 2.4447 (16) and 2.4707 (17) Å. O—H...O Hydrogen bonds link the anions in the hydrogen fumarate salt (XIV), isomeric with (XIII), into chains that are linked into sheets via N—H...O hydrogen bonds. In the hydrogen (2R,3R)-tartrate salt, C11H17N2O+·C4H5O6 −·1.698H2O (XV), the anions are linked into sheets by O—H...O hydrogen bonds. Comparisons are made with the structures of some related compounds.

scholarly journals Twelve 4-(4-methoxyphenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in one, two and three dimensions

2019 ◽  
Vol 75 (10) ◽  
pp. 1494-1506 ◽  
Author(s):  
Haruvegowda Kiran Kumar ◽  
Hemmige S. Yathirajan ◽  
Sabine Foro ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Supramolecular Assembly ◽  
Organic Anions ◽  
Three Dimensions ◽  
Space Group ◽  
Dimensional Array ◽  
A Chain ◽  
Related Compounds

Twelve 4-(4-methoxyphenyl)piperazin-1-ium salts containing organic anions have been prepared and structurally characterized. The monohydrated benzoate, 4-fluorobenzoate, 4-chlorobenzoate and 4-bromobenzoate salts, C11H17N2O+·C7H5O2 −·H2O (I), C11H17N2O+·C7H4FO2 −·H2O (II), C11H17N2O+·C7H4ClO2 −·H2O (III), and C11H17N2O+·C7H4BrO2 −·H2O (IV), respectively, are isomorphous and all exhibit disorder in the 4-methoxyphenyl unit: the components are linked by N—H...O and O—H...O hydrogen bond to form chains of rings. The unsolvated 2-hydroxybenzoate, pyridine-3-carboxylate and 2-hydroxy-3,5-dinitrobenzoate salts, C11H17N2O+·C7H5O3 − (V), C11H17N2O+·C6H4NO2 − (VI) and C11H17N2O+·C7H3N2O7 − (VII), respectively, are all fully ordered: the components of (V) are linked by multiple N—H...O hydrogen bonds to form a chain of rings; those of (VI) are linked into a three-dimensional framework by a combination of N—H...O, C—H...O and C—H...N hydrogen bonds and those of (VII), where the anion has a structure reminiscent of the picrate anion, are linked into a three-dimensional array by N—H...O and C—H...O hydrogen bonds. The hydrogensuccinate and hydrogenfumarate salts, C11H17N2O+·C4H5O4 − (VIII) and C11H17N2O+·C4H3O3 − (IX), respectively, are isomorphous, and both exhibit disorder in the anionic component: N—H...O and O—H...O hydrogen bonds link the ions into sheets, which are further linked by C—H...π(arene) interactions. The anion of the hydrogenmaleate salt, C11H17N2O+·C4H3O3 − (X), contains a very short and nearly symmetrical O...H...O hydrogen bond, and N—H...O hydrogen bonds link the anions into chains of rings. The ions in the trichloroacetate salt, C11H17N2O+·C2Cl3O2 − (XI), are linked into simple chains by N—H...O hydrogen bonds. In the hydrated chloranilate salt, 2C11H17N2O+·C6Cl2O4 2−·2H2O (XII), which crystallizes as a non-merohedral twin, the anion lies across a centre of inversion in space group P21/n, and a combination of N—H...O and O—H...O hydrogen bonds generates complex sheets. Comparisons are made with the structures of some related compounds.

scholarly journals Six 1-halobenzoyl-4-(2-methoxyphenyl)piperazines having Z′ values of one, two or four; disorder, pseudosymmetry, twinning and supramolecular assembly in one, two or three dimensions

2021 ◽  
Vol 77 (1) ◽  
pp. 5-13
Author(s):  
Chayanna Harish Chinthal ◽  
Channappa N. Kavitha ◽  
Hemmige S. Yathirajan ◽  
Sabine Foro ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Supramolecular Assembly ◽  
Three Dimensions ◽  
Coupling Reactions ◽  
Two Dimensional ◽  
Space Group ◽  
A Chain ◽  
And Inversion

Six 1-halobenzoyl-4-(2-methoxyphenyl)piperazines have been prepared using carbodiimide-mediated coupling reactions between halobenzoic acids and N-(2-methoxyphenyl)piperazine. The molecules of 1-(4-fluorobenzoyl)-4-(2-methoxyphenyl)piperazine, C18H19FN2O2 (I), are linked into a chain of rings by a combination of C—H...O and C—H...π(arene) hydrogen bonds. 1-(4-Chlorobenzoyl)-4-(2-methoxyphenyl)piperazine, C18H19ClN2O2 (II), crystallizes in the space group Pca21 with Z′ = 4 and it exhibits both pseudosymmetry and inversion twinning: a combination of six C—H...O and two C—H...π(arene) hydrogen bonds generate a three-dimensional assembly. In 1-(4-bromobenzoyl)-4-(2-methoxyphenyl)piperazine, C18H19BrN2O2 (III), which also crystallizes in space group Pca21 but with Z′ = 2, the bromobenzoyl unit in one of the molecules is disordered. Pseudosymmetry and inversion twinning are again present, and a combination of three C—H...O and one C—H...π(arene) hydrogen bonds generate a two-dimensional assembly. A single C—H...O hydrogen bond links the molecules of 1-(4-iodobenzoyl)-4-(2-methoxyphenyl)piperazine, C18H19IN2O2 (IV), into simple chains but in the isomeric 3-iodobenzoyl analogue (V), which crystallizes in space group P212121 with Z′ = 2, a two-dimensional assembly is generated by a combination of four C—H...O and two C—H...π(arene) hydrogen bonds; pseudosymmetry and inversion twinning are again present. A single C—H...O hydrogen bond links the molecules of 1-(2-fluorobenzoyl)-4-(2-methoxyphenyl)piperazine, C18H19FN2O2 (VI), into simple chains. Comparisons are made with the structures of some related compounds.

scholarly journals BenzimidazoliumL-aspartate

IUCrData ◽  
2016 ◽  
Vol 1 (5) ◽  
Author(s):  
M. Amudha ◽  
P. Praveen Kumar ◽  
G. Chakkaravarthi
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Ring System ◽  
Dimensional Structure ◽  
Carboxyl Groups ◽  
Benzimidazole Ring ◽  
Π Interactions ◽  
Graph Set ◽  
Molecular Salt

In the cation of the title molecular salt, C7H7N2+·C4H6NO4−(systematic name: 1H-benzo[d]imidazol-3-ium 2-azaniumylsuccinate), the benzimidazole ring system is almost planar (r.m.s. deviation = 0.012 Å). The cation is protonated at the N atom and the L-aspartate zwitterion is deprotonated at both carboxyl groups. In the anion, an N—H...O hydrogen bond and an N—H...O short contact generateS(6) graph-set motifs. In the crystal, the anions are linkedviathree N—H...O hydrogen bonds involving the NH3+group, forming layers parallel to theabplane. The benzimidazolium cations are linked to these layers by N—H...O hydrogen bonds. The layers are linkedviaC—H...O hydrogen bonds involving the benzimidazolium cation, forming a three-dimensional structure. There are also C—H...π interactions present involving inversion-related benzimidazolium cations.

scholarly journals Three-dimensional hydrogen-bonded framework structures in flunarizinium nicotinate and flunarizinediium bis(4-toluenesulfonate) dihydrate

2014 ◽  
Vol 70 (8) ◽  
pp. 805-811 ◽  
Author(s):  
Channappa N. Kavitha ◽  
Hemmige S. Yathirajan ◽  
Manpreet Kaur ◽  
Eric C. Hosten ◽  
Richard Betz ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Ion Pairs ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Framework Structure ◽  
Independent Components ◽  
Π Stacking ◽  
Π Stacking Interaction ◽  
Ionic Components

The structures of two salts of flunarizine, namely 1-bis[(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine, C26H26F2N2, are reported. In flunarizinium nicotinate {systematic name: 4-bis[(4-fluorophenyl)methyl]-1-[(2E)-3-phenylprop-2-en-1-yl]piperazin-1-ium pyridine-3-carboxylate}, C26H27F2N2+·C6H4NO2−, (I), the two ionic components are linked by a short charge-assisted N—H...O hydrogen bond. The ion pairs are linked into a three-dimensional framework structure by three independent C—H...O hydrogen bonds, augmented by C—H...π(arene) hydrogen bonds and an aromatic π–π stacking interaction. In flunarizinediium bis(4-toluenesulfonate) dihydrate {systematic name: 1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine-1,4-diium bis(4-methylbenzenesulfonate) dihydrate}, C26H28F2N22+·2C7H7O3S−·2H2O, (II), one of the anions is disordered over two sites with occupancies of 0.832 (6) and 0.168 (6). The five independent components are linked into ribbons by two independent N—H...O hydrogen bonds and four independent O—H...O hydrogen bonds, and these ribbons are linked to form a three-dimensional framework by two independent C—H...O hydrogen bonds, but C—H...π(arene) hydrogen bonds and aromatic π–π stacking interactions are absent from the structure of (II). Comparisons are made with some related structures.

Three closely related thienyl-substituted 1,4-epoxynaphtho[1,2-b]azepines: hydrogen-bonded assembly in one, two and three dimensions

2013 ◽  
Vol 69 (3) ◽  
pp. 307-312 ◽  
Author(s):  
Andrés F. Yépes ◽  
Alirio Palma ◽  
Justo Cobo ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Geometrical Isomer ◽  
Three Dimensions ◽  
Racemic Mixtures ◽  
Hydrogen Bonded

(2R,4S)-2-(3-Methylthiophen-2-yl)-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine, C19H17NOS, (I), crystallizes with a single enantiomer in each crystal, whereas its geometrical isomer (2RS,4SR)-2-(5-methylthiophen-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-naphtho[1,2-b]azepine, (II), and (2RS,4SR)-2-(5-bromothiophen-2-yl)-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine, C18H14BrNOS, (III), both crystallize as racemic mixtures. A combination of one C—H...O hydrogen bond and two C—H...π(arene) hydrogen bonds links the molecules of (I) into a three-dimensional framework; the molecules of (II) are linked into aC(4)C(4)[R22(7)] chain of rings by a combination of C—H...N and C—H...O hydrogen bonds; and in (III), whereZ′ = 2, a combination of four C—H...π(arene) hydrogen bonds and two C—H...π(thienyl) hydrogen bonds links the molecules into complex sheets. Comparisons are made with the assembly patterns in some aryl-substituted 1,4-epoxynaphtho[1,2-b]azepines.

scholarly journals Nine N-aryl-2-chloronicotinamides: supramolecular structures in one, two and three dimensions

2006 ◽  
Vol 62 (4) ◽  
pp. 651-665 ◽  
Author(s):  
Silvia Cuffini ◽  
Christopher Glidewell ◽  
John N. Low ◽  
Aline G. de Oliveira ◽  
Marcus V. N. de Souza ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Supramolecular Structures ◽  
Three Dimensions ◽  
Compound Viii ◽  
Stacking Interactions ◽  
Compound I ◽  
Π Stacking ◽  
Compound Ii

Structures are reported here for eight further substituted N-aryl-2-chloronicotinamides, 2-ClC5H3NCONHC6H4 X-4′. When X = H, compound (I) (C12H9ClN2O), the molecules are linked into sheets by N—H...N, C—H...π(pyridyl) and C—H...π(arene) hydrogen bonds. For X = CH3, compound (II) (C13H11ClN2O, triclinic P\bar 1 with Z′ = 2), the molecules are linked into sheets by N—H...O, C—H...O and C—H...π(arene) hydrogen bonds. Compound (III), where X = F, crystallizes as a monohydrate (C12H8ClFN2O·H2O) and sheets are formed by N—H...O, O—H...O and O—H...N hydrogen bonds and aromatic π...π stacking interactions. Crystals of compound (IV), where X = Cl (C12H8Cl2N2O, monoclinic P21 with Z′ = 4) exhibit inversion twinning: the molecules are linked by N—H...O hydrogen bonds into four independent chains, linked in pairs by C—H...π(arene) hydrogen bonds. When X = Br, compound (V) (C12H8BrClN2O), the molecules are linked into sheets by N—H...O and C—H...N hydrogen bonds, while in compound (VI), where X = I (C12H8ClIN2O), the molecules are linked into a three-dimensional framework by N—H...O and C—H...π(arene) hydrogen bonds and an iodo...N(pyridyl) interaction. For X = CH3O, compound (VII) (C13H11ClN2O2), the molecules are linked into chains by a single N—H...O hydrogen bond. Compound (VIII) (C13H8ClN3O, triclinic P\bar 1 with Z′ = 2), where X = CN, forms a complex three-dimensional framework by N—H...N, C—H...N and C—H...O hydrogen bonds and two independent aromatic π...π stacking interactions.

scholarly journals The crystal structures of three clozapinium salts: different molecular configurations, and supramolecular assembly in one, two and three dimensions

2015 ◽  
Vol 71 (4) ◽  
pp. 406-413 ◽  
Author(s):  
Manpreet Kaur ◽  
Jerry P. Jasinski ◽  
Hemmige S. Yathirajan ◽  
Channappa N. Kavitha ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Dimethyl Sulfoxide ◽  
Three Dimensional ◽  
Supramolecular Assembly ◽  
Three Dimensions ◽  
Planar Geometry ◽  
Compound I ◽  
Protonation Site ◽  
Piperazine Ring ◽  
Compound Ii

The structures of three salts derived from clozapine, 8-chloro-11-(4-methylpiperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine, are reported, namely, clozapinium 3,5-dinitrobenzoate dimethyl sulfoxide monosolvate, C18H20ClN4+·C7H3N2O6−·C2H6OS, (I), where the dimethyl sulfoxide component is disordered over two sets of atomic sites having occupancies 0.627 (2) and 0.373 (2); clozapinium hydrogen maleate 0.21-hydrate, C18H20ClN4+·C4H3O4−·0.21H2O, (II), and clozapinium 2-hydroxybenzoate, C18H20ClN4+·C7H5O3−, (III). In all three salts, the protonation site is the methylated N atom of the piperazine ring, and the dimensions and conformations of the fused tricyclic system are very similar. However, differences are apparent in the piperazine component: in both compounds (II) and (III), the unprotonated N atom of this ring has a pyramidal geometry, but in compound (I) this atom has a planar geometry. In compound (III), both N-substituents in this ring occupy equatorial sites, but in compound (II) the fused tricyclic system occupies an axial site of the piperazine ring. The independent components of compound (I) are linked within the selected asymmetric unit by a combination of N—H...O and C—H...O hydrogen bonds, and these hydrogen-bonded aggregates are linked into chains by an aromatic π–π stacking interaction. In compound (II), the components are linked into sheets by a combination of O—H...O, N—H...O and C—H...O hydrogen bonds, and in compound (III), a combination of N—H...O, C—H...O and C—H...N hydrogen bonds links the components into a three-dimensional framework structure. Comparisons are made with some similar compounds.

Iodo-nitroarenesulfonamides: interplay of hard and soft hydrogen bonds, I...O interactions and aromatic π...π stacking interactions

2001 ◽  
Vol 58 (1) ◽  
pp. 94-108 ◽  
Author(s):  
Craig J. Kelly ◽  
Janet M. S. Skakle ◽  
James L. Wardell ◽  
Solange M. S. V. Wardell ◽  
John N. Low ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Asymmetric Unit ◽  
Space Group ◽  
Rotation Axes ◽  
Π Stacking ◽  
Structural Database ◽  
A Chain

Molecules of N-(4′-iodophenylsulfonyl)-4-nitroaniline, 4-O2NC6H4NHSO2C6H4I-4′ (1), are linked by three-centre I...O2N interactions into chains and these chains are linked into a three-dimensional framework by C—H...O hydrogen bonds. In the isomeric N-(4′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4NHSO2C6H4NO2-4′ (2), the chains generated by the I...O2N interactions are again linked into a three-dimensional framework by C—H...O hydrogen bonds. Molecules of N,N-bis(3′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4N(SO2C6H4NO2-3′)2 (3), lie across twofold rotation axes in space group C2/c and they are linked into chains by paired I...O=S interactions: these chains are linked into sheets by a C—H...O hydrogen bond, and the sheets are linked into a three-dimensional framework by aromatic π...π stacking interactions. In N-(4′-iodophenylsulfonyl)-3-nitroaniline, 3-O2NC6H4NHSO2C6H4I-4′ (4), there are R^2_2(8) rings formed by hard N—H...O=S hydrogen bonds and R^2_2(24) rings formed by two-centre I...nitro interactions, which together generate a chain of fused rings: the combination of a C—H...O hydrogen bond and aromatic π...π stacking interactions links the chains into sheets. Molecules of N-(4′-iodophenylsulfonyl)-4-methyl-2-nitroaniline, 4-CH3-2-O2NC6H3NHSO2C6H4I-4′ (5), are linked by N—H...O=S and C—H...O(nitro) hydrogen bonds into a chain containing alternating R^2_2(8) and R^2_2(10) rings, but there are no I...O interactions of either type. There are two molecules in the asymmetric unit of N-(4′-iodophenylsulfonyl)-2-nitroaniline, 2-O2NC6H4NHSO2C6H4I-4′ (6), and the combination of an I...O=S interaction and a hard N—H...O(nitro) hydrogen bond links the two types of molecule to form a cyclic, centrosymmetric four-component aggregate. C—H...O hydrogen bonds link these four-molecule aggregates to form a molecular ladder. Comparisons are made with structures retrieved from the Cambridge Structural Database.

scholarly journals 14,15-Didehydrohellebrigenin

2012 ◽  
Vol 68 (6) ◽  
pp. o1614-o1615
Author(s):  
Tong Yu ◽  
Hai-Yan Tian ◽  
Xiao-Feng Yuan ◽  
Shu-Zhi Hu ◽  
Ren-Wang Jiang
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Lactone Ring ◽  
Three Dimensional ◽  
Membered Ring ◽  
Envelope Conformation ◽  
Compound C ◽  
Dimensional Network ◽  
Hydroxy Groups

The title compound, C24H30O5, is the didehydro product of the steroid hellebrigenin (systematic name: 3β,5,14-trihydroxy-19-oxo-5β-bufa-20,22-dienolide). It consists of three cyclohexane rings (A, B and C), a five-membered ring (D) and a six-membered lactone ring (E). The stereochemistry of the ring junctions are A/B cis, B/C trans and C/D cis. Cyclohexane rings A, B and C have normal chair conformations. The five-membered ring D with the C=C bond adopts an envelope conformation. Lactone ring E is essentially planar with a mean derivation of 0.006 (4) Å and is β-oriented at the C atom of ring D to which it is attached. There is an O—H...O hydrogen bond in the molecule involving the hydroxy groups. In the crystal, O—H...O hydrogen bonds link the molecules into chains propagating along [010]. The chains are linked by C—H...O contacts into a three-dimensional network.

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