A series of 2-pyridones and their methyl derivatives has been studied in term of noncovalent interactions and molecular packing properties. These structural characteristics were then correlated with the quantitative analysis of the intermolecular interactions governing those compounds in three dimensional net. The electronic effect over the 2-pyridone ring on the packing property was analysed by locking the tautomers. The SC-XRD revealed that 4,6-dimethyl-3-cyano-2-pyridone and its O-methyl derivative owned the layered arrangement, while N-methyl derivative possessed the corrugated arrangement with persistent of stacking between two pyridone rings. However, 4-phenyl-6-methyl-3-cyano-2-pyridone and its N-methyl derivative showed the reverse face-to-face stacking due to modest torsion of bi-aryl rings. Similarly, 6-phenyl-4-methyl-3-cyano-2-pyridone has also shown reverse face-to-face stacking while its N-methyl derivative stacking between pyridone ring and nitrile group was observed. Further, quantitative analysis of intermolecular interactions was done through Hirshfeld surface analysis and density functional theory.

Here, we first time report the flexible tripodal molecules, contained propylene as a linker, thiocyanuric acid as central core and, p-nitro phenol 1 and pyridazinone 2 as terminal for conformational studies. The conformational studies of these tripodal molecules have been carried by X-ray crystallography, 2D-NOESY spectra and computational studies. Both the molecules have shown folded conformations in solid and solution state however solid state conformation is not stable in gaseous state.

A simple and efficient synthesis of new spiro heterocyclic skeleton, 3′-vinyl-2′,3′-dihydrospiro[chroman-3,4′-oxepino[3,2-c]chromene]-2,4,6′(5′H)-triones by an unusual one pot tandem RCM–Claisen rearrangement of O-allyl biscoumarins is described. A new example of a coumarin derivative containing seven membered cyclic ether.

Weak noncovalent interactions are the basic forces in crystal engineering. Polymorphism in flexible molecules is very common, leading to the development of the crystals of same organic compounds with different medicinal and material properties. Crystallization of 2,2′-{[1,2-phenylenebis(methylene)]bis(sulfanediyl)}bis(4,6-dimethylnicotinonitrile) by evaporation at room temperature from ethyl acetate and hexane and from methanol and ethyl acetate gave stable polymorphs 4a and 4b, respectively, while in acetic acid, it gave metastable polymorph 4c. The polymorphic behavior of the compound has been visualized through single-crystal X-ray and Hirshfeld analysis. These polymorphs are tested for anti-inflammatory activity via the complete Freund's adjuvant-induced rat paw model, and compounds have exhibited moderate activities. Studies of docking in the catalytic site of cyclooxygenase-2 were used to identify potential anti-inflammatory lead compounds. These results suggest that the supramolecular aggregate structure, which is formed in solution, influences the solid state structure and the biological activity obtained upon crystallization.

In the title ferrocene derivative, [Fe(C5H5)(C9H8NO)], the dihedral angle between the ene-nitrile group and the substituted cyclo-penta-dienyl ring is 71.2 (1)°. The cyclopentadienyl rings of the ferrocene moiety are arranged in an eclipsed conformation. The hy-droxy group, and the corresponding methine H atom, are disordered over two sets of sites with site-occupancy factors of 0.744 (4) and 0.256 (4). An intra-molecular C-H⋯O close contact is observed. In the crystal, O-H⋯N hydrogen bonds form a C(6) chain along [100].

Two tosylate salts of an anticancer drug lapatinib, viz . a monotosylate [systematic name: ({5-[4-({3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}amino)quinazolin-6-yl]furan-2-yl}methyl)[2-(methylsulfonyl)ethyl]azanium 4-methylbenzenesulfonate], C 29 H 27 ClFN 4 O 4 S + ·C 7 H 7 O 3 S − , (I), and a ditosylate [systematic name: 4-({3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}amino)-6-]5-({[2-(methylsulfonyl)ethyl]azaniumyl}methyl)furan-2-yl[quinazolin-1-ium bis(4-methylbenzenesulfonate)], C 29 H 28 ClFN 4 O 4 S 2+ ·2C 7 H 7 O 3 S − , (II), were obtained during crystallization attempts for polymorphism. In both structures, the lapatinib cation is in a distorted U-like conformation and the tosylate anion is clamped between the aniline N atom and methylamine N atom through N—H...O hydrogen bonds, forming an R 2 2 (15) ring motif. The 4-anilinoquinazoline ring system is essentially planar in (I), while it is twisted in (II), controlled by an intramolecular C—H...N interaction. In (I), alternating cations and anions are linked by N—H...O hydrogen bonds into C 2 2 (6) chains. These chains are linked by cations in a helical manner. The presence of the additional tosylate anion in (II) results in the formation of one-dimensional tapes of fused hydrogen-bonded rings through N—H...O and C—H...O interactions. These studies augment our understanding of the role of nonbonded interactions in the solid state, which is useful for correlation to the physicochemical properties of drug products.

Ninhydrin guanidinium chloride (3a,8b-dihydroxy-4-oxo-1H,2H,3H,3aH,4H,8bH-indeno [1,2-d]imidazolidin-2-iminium chloride) a semiorganic crystal was synthesized. The structure was determined using X-ray single crystal technique. Comparisons between the FT-IR spectrum of ninhydrin guanidinium chloride with ninhydrin were made. Melting point was found using thermal measurements. The molecular geometry, vibrational frequencies and Mulliken charges of the compound in the ground state have been calculated by the density functional theory (DFT) method with 3-21G(d,p) basis set and theoretical frequencies were compared with the experimental FT-IR spectrum. Besides, molecular electrostatic potential (MEP), frontier molecular orbitals (FMO) analysis, natural bond orbitals (NBO) and thermodynamic properties at various temperatures of the compound were investigated by theoretical calculations.

4-Chloro-2-aryl-2H-3-chromenecarbaldehydes 3a-g on reaction with malononitrile in ethanol in the presence of piperidine gave 5-aryl-2-piperidino-5H-chromeno[3,4-c]pyridine-1-carbonitriles 4a-g in good yields.

A new coordination polymer namely [[Ca6(H–gly)12(H2O)18]Cl12·6H2O]n (1) (H–gly = glycine) has been isolated from the calcium chloride–glycine–water system and structurally characterized. Each Ca(II) in 1 is eight-coordinated and is bonded to eight oxygen atoms three of which are from terminal water molecules and five oxygen atoms from four symmetry related zwitterionic glycine ligands. The H–gly ligands exhibit two different binding modes viz. a monodentate carboxylate ligation and a μ3-tetradentate bridging carboxylate binding mode, which results in the formation of a one-dimensional coordination polymer. In the infinite chain the Ca(II) atoms are organized in a zigzag fashion. A comparative study reveals a rich and diverse structural chemistry of calcium halide–glycine compounds.

In the title compound, C9H13N2O +.Cl-, the cation, apart from the methyl groups, is almost planar, with a maximum deviation of 0.040 (1) A(degrees); the methyl C atoms deviate by 0.389 (2) and-1.247 (1) A(degrees), from the mean plane. In the crystal, cations and anions associate through C-H...Cl hydrogen bonds, forming a helical arrangement. In addition, intermolecular O-H...Cl, N-H...Cl and C-H...N interactions are observed.

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

The title complex, bis [2-(4-methylphenyl)-1-phenethyl-4(1H)-quinazolinone] dichlorocopper (II) was synthesized and characterized by single-crystal and powder X-ray diffraction, IR–UV spectra, elemental analyses, 1H and 13C NMR and thermogravimetric analyses. Crystal structure determination reveals that the complex consists of mononuclear units with copper (II) ion coordinating in a bis-bidentate fashion. The copper (II) ion is located on the inversion center and has an octahedral coordination environment. The conformation of the dihydropyrimidine (DHPM) ring is almost planar unlike a sofa, as in the case of pure ligand. No classical hydrogen bonds were observed in the structure. The optimized geometrical parameters were calculated using the methods based on the density functional theory (DFT). A comparison of the molecular conformation and geometrical parameters obtained from the X-ray structure analysis and the theoretical study clearly indicates that the DFT calculations agree closely the X-ray structure. The investigated complex along with the ligand has been screened simultaneously for in vitro antibacterial and antifungal activities and compared with the drugs in use.

The title compound [In(C22H30N4O4)]Cl (I) bis[(N-salicylidene-N′-(2-hydroxyethyl)ethyleneediamine) indium(III) chloride is prepared, and its crystal structure is determined by single crystal X-ray diffraction at room temperature. The complex crystallizes in the monoclinic space group P21/n, a = 9.9704(6) Å, b = 24.9554(15) Å, c = 10.5707(6) Å, β = 116.46(2)°, V = 2354.6(2), Z = 4. The X-ray analysis reveals that the InIII ion is surrounded by four nitrogen and two oxygen atoms from two ligands leading to a distorted octahedral geometry. The molecule has the form of tongs at a junction point with the metal. Five membered rings adopt envelope conformation. In the crystal structure, the molecules are linked via N-H...Cl, O-H...O, O-H...Cl, and C-H...Cl intermolecular interactions. The structure is further stabilized by C-H...π (arene) interactions.

In the title compound, C32H28N2O2, the pyrrolidine ring adopts an envelope conformation, whereas the cyclohexanone ring in the tetrahydronaphthalene fused-ring system adopts a half-chair conformation. The oxindole ring system is oriented at an angle of 48.2 (1)° with respect to the naphthyl ring system. An intramolecular C—H...O close contact is observed. In the crystal, molecules associate via two C—H...O hydrogen bonds, forming R22(14) and R22(10) dimers.

The crystal structures of three salts and two solvated multicomponent crystals of lamotrigine with 4-fluorobenzoic acid, nicotinic acid, 2-thiobarbituric acid, 3-picoline and butyl alcohol are reported. Compound 1a crystallizes in monoclinc system, space group P2 1 with a = 13.3860(5) Å, b = 8.3420(3) Å, c = 15.5200(6) Å, β = 93.524(1)°, V = 1729.78(11) Å 3 , and Z = 2. Compound 1b crystallizes in monoclinic system, space group P2 1 /c with a = 10.6625(7) Å, b = 16.2575(11) Å, c = 13.6346(9) Å, β = 100.904(1)°, V = 2320.8(3) Å 3 , and Z = 4. Compound 1c crystallizes in triclinic system, space group P 1 , with a = 10.1309(7) Å, b = 12.0260(8) Å, c = 14.0826(10) Å, α = 71.783(1)°, β = 86.451(1)°, γ = 80.902(1)°, V = 1609.10(19) Å 3 , and Z = 1. Compound 1d crystallizes in monoclinic system, space group P2 1 /c with a = 14.9570(10) Å, b = 8.0230(6) Å, c = 13.8162(10) Å, β = 102.884(1)°, V = 1616.2(2) Å 3 , and Z = 4. Compound 1e crystallizes in triclinic system, space group P 1 , with a = 7.5710(6) Å, b = 8.5721(7) Å, c = 13.5532(11) Å, α = 85.364(1)°, β = 79.632(1) (1)°, γ = 86.188(1)°, V = 861.19(12) Å 3 , and Z = 2. Characteristic R 2 2 (8) dimer is observed in all five structures. A complete hydrogen bonded motif analysis is described. Lamotrigine-lamotrigine base pair is observed in all the structures, except in ( 1b ). In ( 1c ), the R 2 2 (7) dimer is noticed while, in all other structures R 2 2 (8) dimer exist between the lamotrigine-lamotrigine base pair. In all the six structures, chlorine atoms of the lamotrigine molecules are not involved in any interactions. Graphical Abstract In the present study we have described the crystal structure and conformation of lamotrigine with three salts viz., fluorobenzoic acid, nicotinic acid and 2-thiobarbituric acid and also with two solvates viz., 3-picoline and butyl alcohol.

ChemInformVolume 42, Issue 50 Natural Products ChemInform Abstract: Cytotoxic Diterpenoid Quinonemethides from the Roots of Pygmacopremna herbacea. K. Satish, K. Satish Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorM. V. P. S. Vishnuvardhan, M. V. P. S. Vishnuvardhan Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorV. Lakshma Nayak, V. Lakshma Nayak Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorG. Srihari, G. Srihari Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorM. Subrahamanyam, M. Subrahamanyam Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorT. Prabhakar Rao, T. Prabhakar Rao Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorS. Ramakrishna, S. Ramakrishna Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorK. Ravikumar, K. Ravikumar Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorB. Sridhar, B. Sridhar Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorM. Marthanda Murthy, M. Marthanda Murthy Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this author K. Satish, K. Satish Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorM. V. P. S. Vishnuvardhan, M. V. P. S. Vishnuvardhan Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorV. Lakshma Nayak, V. Lakshma Nayak Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorG. Srihari, G. Srihari Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorM. Subrahamanyam, M. Subrahamanyam Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorT. Prabhakar Rao, T. Prabhakar Rao Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorS. Ramakrishna, S. Ramakrishna Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorK. Ravikumar, K. Ravikumar Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorB. Sridhar, B. Sridhar Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this authorM. Marthanda Murthy, M. Marthanda Murthy Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 607, IndiaSearch for more papers by this author First published: 17 November 2011 https://doi.org/10.1002/chin.201150174Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume42, Issue50December 13, 2011 RelatedInformation

In the title compound, C32H25NO3, the pyrrolidine ring adopts an envelope conformation, whereas the cyclohexanone ring in the tetrahydronaphthalene fused-ring system adopts a half-chair conformation. The indanedione unit is oriented at an angle of 58.9 (1)° with respect to the naphthyl ring system. Three intramolecular C—H⋯O close contacts and an intramolecular C—H⋯π interaction are observed. In the crystal, molecules associate via C—H⋯O hydrogen bonds, forming a helical chain with a C(10) motif along the b axis.

Weak interactions usually show a versatile property to stabilize the molecular conformation and crystal packing in solid state. Crystal packing and conformational property of the synthesized compound 1(3-cyano-4,6-dimethyl nicotinonitril-1-yl)-3-(phalimido-1-yl)-1-thioxyethane (2) is stabilized by CH center dot center dot center dot O, CH center dot center dot center dot N, and CH center dot center dot center dot pi interactions.

In the title compound, C32H28N2O2, the pyrrolidine ring adopts an envelope conformation, whereas the cyclohexanone ring in the tetrahydronaphthalene fused-ring system adopts a half-chair conformation. The oxindole ring system is oriented at an angle of 48.2 (1)° with respect to the naphthyl ring system. An intramolecular C—H⋯O close contact is observed. In the crystal, molecules associate via two C—H⋯O hydrogen bonds, forming R 2 2(14) and R 2 2(10) dimers.

In solution state, the stable gauche conformation of 1,3-bis(4,6-dimethyl-1H-nicotinonitril-1-yl)1,3-dithioxypropane is predicted by CD spectra. Weak interaction present in the molecule makes it flexible, and due to this reason helicity is observed in it. In solid state, the molecular conformation and packing geometry is stabilized via both intra/inter molecular CH···N, CH···S and π···π interactions.