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In the paper by Manikandan et al. [IUCrData (2017). 2, x170376], a proton on the indole N was missed in the structure solution. The proton is now added and the changes are reported here. The title, scheme, Figs. 1 and 2, the hydrogen-bonding table, the crystallographic data table and description of the supramolecular architectures are corrected.

Abstract  The title compound, C9H10O2S, (I), crystallizes in the triclinic space group, P − 1, with unit cell parameters a = 6.2249(3), b = 7.3733(5), c = 19.5708(12), Å, α = 86.746(5)°, β = 88.682(5)°, γ = 86.988(5)°, Z = 4. The molecule consists of a methyl sulfanyl group bonded to benzyl acetic acid at the 4 position crystallizing with two molecules in the asymmetric unit. The carboxylic acid group from the acetic acid moiety in these two molecules forms a classic O–H···O hydrogen bonded dimer with O···O distances of 2.673(2) and 2.646(2) Å, in a R22 (8) graph-set motif which link the molecules into pairs around inversion centers in the unit cell. The dihedral angles between the mean planes of the R22 (8) graph-set motif with the mean planes of the two nearby benzyl groups within the same dimer in the unit cell are 64.1(6)° and 71.3(4)°, respectively. Within the same dimer the dihedral angle between the two benzyl groups is 45.2(1)°. The structure is supported by a weak intermolecular C–H···Cg π-ring interaction and gives support to molecular packing stability in the unit cell. Comparison to a MOPAC AM1 computational calculation provides support to these observations. Graphical Abstract  The crystal structure of [4-(methylsulfanyl)phenyl]acetic acid is investigated. The molecule, C9H10O2S, crystallizes in the triclinic space group, P − 1, with two molecules in the asymmetric unit. The carboxylic acid group from the acetic acid moiety in these two molecules forms a classic O–H···O hydrogen bonded dimer in a R22 (8) graph-set motif which link the molecules into pairs around inversion centers in the unit cell. Its geometric and packing parameters are described and compared to a MOPAC AM1 computational calculation. [ABSTRACT FROM AUTHOR]

Abstract  The title compound, a salt of C13H20O2 2 2Cl− 0.5 H2O, (I), crystallizes in the monoclinic space group C 2/c with unit cell parameters a = 34.091(4) Å, b = 7.2312(4) Å, c = 12.5827(5) Å, β = 96.870(6)°, Z = 8. The dihedral angle between the mean plane of the benzyl ring and the piperazin-1-yl group is 80.4(2)°, while the angle between the mean planes of the carbonyl group with that of the benzyl and piperazin-1-yl rings measure 6.6(3)° and 76.8(3)°, respectively. A short C=O and slightly extended C–O carboxyl bond in concert with weak intermolecular C–O···Cg π-ring interactions influences this twist angle with the benzyl ring and provides a slight interaction with the π conjugation of the benzene ring. Hydrogen bonding has no effect on the carboxylic group. Two separate two-center (acceptor bifurcated) Cl−···H–(N,O) hydrogen bonds are observed between one chloride anion and a water molecule and the piperazin-1-yl ring and a second chloride anion with a carboxyl oxygen atom and the piperazin-1-yl ring. These direct intermolecular couplings link the molecule into chains along the [010] plane of the unit cell which influence the twist angles of the benzyl and piperazin-1-yl rings and help stabilize crystal packing in the unit cell. Graphical Abstract  Crystal Structure of 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride hemihydrate is reported and its geometric and packing parameters described and compared to a MOPAC computational calculation. [ABSTRACT FROM AUTHOR]

Abstract  Gabapentin hydrochloride hemihydrate, a derivative of Gabapentin [or 1-(aminomethyl) cyclohexaneacetic acid; Gpn, C6H17NO2], is a salt of C9H18NO2 + Cl− 0.5 H2O, which crystallizes in the monoclinic space group I 2/a with unit cell parameters a = 13.2467(3), b = 6.5552(2), c = 26.0094(8) Å, β = 96.561(3)°, Z = 8. The crystal structure and bonding network is compared to its isostructural and previously reported polymorphic derivative, Gpn hydrochloride hemihydrate [C9H17NO2 HCl ½ H2O]. Both of these derivatives exhibit extensive inter and intra molecular hydrogen bonding networks between the NH3 + group and neighboring Cl−, water and carboxyl oxygen atoms as well as similar interactions between the chloride anion and nearby water and carboxyl oxygen atoms. A unique and relatively rare three-center hydrogen bond configuration (with a bifurcated chlorine Cl−···H–(N,O) and Cl−···H–O acceptor hydrogen bonds) as well as N–H···O donor hydrogen bonds can be seen linking the molecules into chains along the [1 0 1] plane of the unit cell. Graphical Abstract  Crystal structure of a second polymorph of gabapentin hydrochloride hemihydrate is reported and its geometric and packing parameters described and compared to the first polymorph and to a MOPAC computational calculation. [ABSTRACT FROM AUTHOR]

Abstract  The title compound, C18H18BrN3O3S, a derivative of 1,3,4-oxadiazole, crystallizes in the triclinic space group P-1 with unit cell parameters a = 6.8731(3), b = 8.9994(4), c = 15.7099(6) Å, α = 92.779(3)°, β = 130.575(3)°, γ = 107.868(4)°, Z = 2. The dihedral angle between the mean planes of the planar naphthyl and morpholine (chair) rings with the planar oxadiazol ring is 50.1(8) and 76.8(6)°, respectively. The planar naphthyl ring is twisted 52.2(5)° with the mean plane of the morpholine ring. A group of four intermolecular close contacts are observed between a bromine atom and hydrogen atoms from the closely packed naphthyl, morpholine and oxy–methyl groups in the unit cell. These molecular interactions in concert with an additional series of π–π stacking interactions that occur between the center of gravity of the two 6-membered rings of the naphthalene group influence the twist angles of each of these three groups. A MOPAC AM1 calculation of the conformation energy of the crystal structure [226.0128(9) kcal] compared to that of the minimum energy structure after geometry optimization [29.9744(1) kcal] reveals a significantly reduced value. The twist angles of the three groups above also change after the AM1 calculation giving support to the influence of both intermolecular C–H···Br short-range interactions and Cg π–π stacking interactions on these angles which therefore play a role in stabilizing crystal packing. Graphical Abstract  Crystal structure of 5-{[(6-bromonaphthalen-2-yl)oxy]methyl}-3-(morpholin-4-ylmethyl)-1,3,4-oxadiazole-2(3H)-thione, C18H18BrN3O3S, is reported and its geometric and packing parameters described and compared to a MOPAC computational calculation. [ABSTRACT FROM AUTHOR]

Abstract  The title compound, C9H8O4, (I), crystallizes in the monoclinic space group P 21/c with unit cell parameters a = 7.3380(5) Å, b = 9.3790(7) Å, c = 12.3172(9) Å, β = 90.687(7)°, Z = 4. The molecule consists of a benzene ring fused to a 1,4 dioxane ring in a half-chair conformation with a carboxylic acid group bonded at the dioxane 2-position. The carboxylic acid group forms a classic O–H···O hydrogen bonded dimer with an O···O distance of 2.6292(12) Å in a R22 (8) graph-set motif which links the molecules into pairs around inversion centers in a supramolecular assembly in the unit cell. The dihedral angle between the mean planes of the R22 (8) graph-set motif’s of two adjacent dimers in the unit cell is 75.7(5)°. The mean plane of an R22 (8) graph-set motif makes an angle of 88.4(5)° with the mean plane of the benzene ring in the same dimer and 13.1(2)° or 13.4(7)° with the mean plane of a benzene ring from an adjacent dimer. Additional weak Cg π-ring intermolecular interactions significantly influence the bond distances, bond angles and torsion angles of the dioxane ring and attached carboxyl group. Comparison to a MOPAC AM1computational calculation provides support to these observations. Graphical Abstract  The association of carboxylic acid dimers in the supramolecular assembly of (R)-1,4-benzodioxane 2-carboxylic acid is investigated by examination of its crystal structure. Its geometric and packing parameters are described and compared to a MOPAC AM1 computational calculation. [ABSTRACT FROM AUTHOR]

Abstract  The title compound, C23H38N2O2, is the saturated form of a modified steroid derivative Finasteride, containing a δ-lactamide ring, fused to successive cyclohexane and cyclopentane rings which contain a tert-butylamide residue. It crystallizes in the monoclinic space group C2 with unit cell parameters a = 9.99450(10), b = 7.67870(10), c = 28.4954(3), Å, β = 93.8706(10)°, Z = 4. Crystal packing effects are influenced by intermolecular hydrogen bond interactions dominated by an acceptor O···H–(C, N) four-center hydrogen bond interaction around the keto oxygen atom from the δ-lactamide ring in the asymmetric unit. Intramolecular three-center C–H···O hydrogen bonds around the tert-butylamide oxygen atom appear to have little effect on crystal packing. A comparison of the geometric parameters of the asymmetric unit (a 5α isomer) is made and with a solvated analog compound (a 5β isomer) and some solvated Finasteride compounds which differ only in the unsaturation of the C1=C2 bond in the δ-lactamide ring. The dihedral angle between the mean planes of the fused δ-lactamide and cyclohexane rings is 2.5(8)° which differs significantly from the 74.8(8) and 76.1(9)° values observed in the solvated analog compound and with its geometry optimized (MOPAC) computed structure, respectively. Index Abstract  Crystal structure of 3-oxo-4-aza-5-alpha-androstone-17 β-tert-butyl carboxamide with an O···H–(C, N) acceptor four-center hydrogen bond around the keto oxygen atom from the δ-lactamide ring in the asymmetric unit is reported and its geometric and packing parameters described and compared to related solvent and analog compounds and to a MOPAC computational calculation of the geometry optimized molecule. [ABSTRACT FROM AUTHOR]

Abstract  The title compound, C13H16O6N3F, features a central furan ring containing four carbon atom chiral centers with a 4-amino-5-fluoro-2-oxopyrimidine group, two acetyl groups and a methyl group bonded at the 2,3,4,5 positions, each in an absolute R configuration (2R,3R,4R,5R). It crystallizes in the monoclinic space group C2 with unit cell parameters a = 14.5341(3), b = 7.26230(10), c = 16.2197(3) Å, β = 116.607(2)°, Z = 4. An extensive array of intra and intermolecular hydrogen bond interactions dominate crystal packing in the unit cell highlighted by a relatively rare three-center proton-bifurcated donor N–H···(O,F) hydrogen bond interaction in cooperation with a second, (C,N)–H···O bifurcated acceptor three-center hydrogen bond in a supportive fashion. Additional weak Cg π-ring intermolecular interactions between a fluorine atom and the 4-amino-5-fluoro-2-oxopyrimidine ring in concert with multiple donor and acceptor hydrogen bonds significantly influence the bond distances, bond angles and torsion angles of the deoxy-5-fluorocytidine group. Comparison to a MOPAC computational calculation provides support to these observations. Index Abstract  Crystal structure of (2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate with dual N–H···(O,F) proton donor bifurcated and (C,N)–H···O bifurcated acceptor three-center hydrogen bond configurations is reported and its geometric and packing parameters described and compared to a MOPAC computational calculation. [ABSTRACT FROM AUTHOR]

Abstract  The structure of an Fe(III) complex of reduced Schiff base is reported. The title compound, C21H30ClFeN4O6 (I), crystallizes in the monoclinic space group P21/n with cell constants: a = 9.988(2) Å, b = 20.430(5) Å, c = 11.415(3) Å, β = 105.480(4)°. It contains a six-coordinate FeN4O2 cation where the ligand is a reduced Schiff base resulting from the NaBH4 reduction of the condensation product between salicylaldehyde and 1,4,8,11-tetraazaundecane. Due to the increased flexibility of the saturated backbone of the ligand compared to the Schiff base from which it was synthesized, the complex adopts a trans-FeN4O2 conformation. There is extensive hydrogen bonding between the amine H atoms and the anion O atoms. Index Abstract  The structure of an Fe(III) complex of reduced Schiff base is reported which adopts a trans-FeN4O2 conformation where the ligand is a reduced hexadentate Schiff base resulting from the NaBH4 reduction of the condensation product between salicylaldehyde and 1,4,8,11-tetraazaundecane. [ABSTRACT FROM AUTHOR]

Abstract  In the molecular structures of three new structurally related chalcone derivatives, namely (2E)-1-(2-hydroxyphenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one, C20H16O3, I, (2E)-1-(2-chloropyridin-4-yl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one, C19H14ClNO2, II, and (2E)-3-(6-methoxy-2-naphthyl)-1-pyridin-4-ylprop-2-en-1-one, III, C19H15NO2, the configuration of the keto group is syn with respect to the olefinic double bond. In all three structures the molecules pack with weak intermolecular C–H···O interactions utilizing both the methoxy and keto oxygen’s in I, the methoxy oxygen in II and the keto oxygen in III. These interactions link the molecules into chains diagonally along the (011) plane of the unit cell in I and III and along the (010) plane in II. The dihedral angle between the phenyl and 2-napthyl rings in I is 31.7(3)°. In II and III the dihedral angle between the pyridyl and 2-naphthyl rings is 14.4(9)° and 1.8(9)°, respectively. C–H···O hydrogen bonding interactions influence these twist angles of these rings in I–III while weak π–π stacking interactions between naphthyl rings in I and III and also between pyridyl and naphthyl rings in II help stabilize crystal packing. [I: P2 1 /c, a = 7.6635(4) Å, b = 11.8047(6) Å, c = 16.7584(7) Å, β = 99.271(5)°, V = 1496.25(13) Å3; II: Pbca, a = 14.1424(4) Å, b = 6.0957(2) Å, c = 33.1458(11) Å, V = 2857.43(16) Å3; III: P2 1 /c, a = 11.5155(4) Å, b = 6.0020(2) Å, c = 22.4645(8) Å, β = 103.002(4)°, V = 1512.85(9) Å3]. Index Abstract  Crystal structures from three Chalcones derived from 6-methoxy-2-naphthaldehyde are reported and their geometric and packing parameters described. [ABSTRACT FROM AUTHOR]

Abstract  Three new coordination complexes of Zn(II) and Mn(II) have been synthesised using two different tridentate N,N,O donor hydrazone ligands, Hpbh and Hacpbh respectively. The complexes [Zn(pbh)2] (1) and [Zn(acpbh)2] (2) have been synthesized by the treatment of ZnSO4 · 7H2O with Hpbh and Hacpbh hydrazone ligands, respectively. The Mn(II) complex [Mn(acpbh)2] (3) was obtained on reacting Mn(NO3)2 · 4H2O with the ligand Hacpbh. The ligands Hpbh and Hacpbh were prepared by condensing pyridine-2-carboxaldehyde and 2-acetylpyridine with benzhydrazide respectively. Inspite of varying the carbonyl functionality attached to the pyridine moiety present in the hydrazone ligands in both the Schiff bases, we obtained three mononuclear complexes 1, 2, and 3 which were clearly characterized from single crystal X-ray diffraction studies. Spectroscopic investigations like IR and UV/Vis have been carried out for 1, 2, and 3. Fluorescence studies have been performed for 1 and 2. For 3 cyclic voltammetry, room temperature magnetic study and EPR measurements have been recorded. [ABSTRACT FROM AUTHOR]

Abstract  Reactions of equimolar quantities of potassium 2-{[(2Z)-3-hydroxy-1-methyl-2-butenylidene]amino}acetate, with R n SnX4−n (R: benzyl– and n=2 or 3) in methanol yielded products of compositions LHSn(PhCH2)3 and LSn(PhCH2)2, respectively. The complexes were characterized by microanalysis, IR, NMR (1H, 13C, 119Sn) and 119mSn Mssbauer spectroscopy. A full characterization of the structure of the complex, tribenzyl{2-{[(2Z)-3-hydroxy-1-methyl-2-butenylidene]amino}acetato}tin(IV), was carried out by single crystal X-ray crystallography. The compound exists as centrosymmetric dimers in which two ligand molecules bridge the two tin centres. Each of the tin atoms in the dimeric unit is five coordinate in an approximately trigonal bipyramidal configuration, with carbon atoms in the equatorial positions and oxygen atoms arranged axially. [ABSTRACT FROM AUTHOR]

Abstract  The crystal structure of (1-naphthyl)(4-methyl- phenyl)tellurium(IV) dibromide, the first unsymmetrical naphthyl containing diorganotellurium(IV) dibromide, shows the formation of one-dimensional supramolecular arrays where TeBr secondary bonds link two parallel rows of molecules in a gear-teethed fashion. The weaker C–HBr and C–Hπ hydrogen bonds play important role in the formation of three-dimensional crystal lattice by cross linking these supramolecular motifs. [ABSTRACT FROM AUTHOR]

Abstract  The crystal structures of four organoselenium compounds, viz. bis(2-formylphenyl)diselenide (5), bis(2-methylnaphthyl)diselenide (6), organoselenenyl sulfide (7), and spiroselenurane (8) are described. Crystal data for 5: space group Pca21, crystal system orthorhombic, a=7.9969(4) , b=20.8794(12) , c=15.8307(13) , Z=8, R=0.0292. Owing to the presence of a strong SeO interaction in compound 5 the geometry around the selenium atom may be considered as T-shaped. Crystal data for 6: space group Pna21, crystal system orthorhombic, a=18.2253(12) , b=13.0714(8) , c=7.7355(5) , Z=4, R=0.0570. The molecule has a cisoid conformation. Crystal data for 7: space group Pbcn, crystal system orthorhombic, a=22.2144(13) , b=8.0255(4) , c=15.4496(9) , Z=8, R=0.0292. Due to intramolecular SeN interaction in 7 the geometry around selenium is T- shaped. Crystal data for 8: space group P21/c, crystal system monoclinic, a=7.4585(5) , b=19.5634(13) , c=8.0428(5) , β=97.1320(10), Z=4, R=0.0254. The O−Se−O angle is 172.86(6). [ABSTRACT FROM AUTHOR]

New complexes of general formula, [M(NNS)Cl] (M = PdII, PtII; NNS = anionic forms of the 6-methyl-2-formylpyridine Schiff bases of S-methyl- and S-benzyldithiocarbazates) have been prepared and characterized by a variety of physico-chemical techniques. Based on conductance and spectral evidence, a square-planar structure is assigned to these complexes. The crystal and molecular structure of the [Pd(mpasme)Cl] complex (mpasme=anionic form of the 6-methyl-2-formylpyridine Schiff base of S-methyldithiocarbazate) has been determined by X-ray diffraction. The complex has a distorted square-planar geometry with the ligand coordinated to the palladium(II) ion via the pyridine nitrogen atom, the azomethine nitrogen atom and the thiolate sulfur atom; the fourth coordination position around the palladium(II) ion is occupied by the chloride ligand. The distortion from a regular square-planar geometry is ascribed to the restricted bite angle of the ligand. Both the Schiff bases exhibit strong cytotoxicity against the human ovarian cancer (Caov-3) cell lines, the S-methyl derivative being two times more active than the S-benzyl derivative. The [Pt(mpasme)Cl] complex is moderately active but the palladium(II) complex is weakly active against this cancer. None of the complexes of Hmpsbz are active against Caov-3. The Schiff base, Hmpasme exhibits moderate activity against the bacteria, MRSA, P. aeruginosa and S. typhimurium but is inactive against B. subtilis. Coordination of the ligand with palladium(II) substantially reduces its activity. The Schiff base, Hmpasbz and its palladium(II) and platinum(II) complexes are inactive against these bacteria. The Schiff bases and their palladium(II) and platinum (II) complexes are inactive against the pathogenic fungi, C. albican, Aspergillus ochraceous and Saccharomyces cerevisiae. [ABSTRACT FROM AUTHOR]