The role of halogen bonding in the interaction landscape directing the crystal packing in a homologous series of halogenated coumarin derivatives

[1]  Ahmed M. Shawky,et al.  Type I–IV Halogen⋯Halogen Interactions: A Comparative Theoretical Study in Halobenzene⋯Halobenzene Homodimers , 2022, International journal of molecular sciences.

[2]  U. Rashid,et al.  N-Arylation of Protected and Unprotected 5-Bromo-2-aminobenzimidazole as Organic Material: Non-Linear Optical (NLO) Properties and Structural Feature Determination through Computational Approach , 2021, Molecules.

[3]  Y. Yoshida,et al.  Chiral Hypervalent Bromine(III) (Bromonium Salt): Hydrogen- and Halogen-Bonding Bifunctional Asymmetric Catalysis by Diaryl-λ3-bromanes , 2021, ACS Catalysis.

[4]  P. Beer,et al.  Hydrosulfide (HS−) Recognition and Sensing in Water by Halogen Bonding Hosts , 2021, Angewandte Chemie.

[5]  U. Englert,et al.  Hydrogen-Bonded and Halogen-Bonded: Orthogonal Interactions for the Chloride Anion of a Pyrazolium Salt , 2021, Molecules.

[6]  M. J. Turner,et al.  CrystalExplorer: a program for Hirshfeld surface analysis, visualization and quantitative analysis of molecular crystals , 2021, Journal of applied crystallography.

[7]  Waya S. Phutdhawong,et al.  Synthesis and Biological Activity Evaluation of Coumarin-3-Carboxamide Derivatives , 2021, Molecules.

[8]  T. Al-Warhi,et al.  Recent advancements of coumarin-based anticancer agents: An up-to-date review. , 2020, Bioorganic chemistry.

[9]  R. Capasso,et al.  Coumarins and Coumarin-Related Compounds in Pharmacotherapy of Cancer , 2020, Cancers.

[10]  S. Dallavalle,et al.  An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities , 2020, International journal of molecular sciences.

[11]  F. Meyer,et al.  Halogen bonding for molecular recognition: new developments in materials and biological sciences. , 2020, Chemical communications.

[12]  Enrico Margiotta,et al.  Halogen Bonds in Ligand–Protein Systems: Molecular Orbital Theory for Drug Design , 2020, J. Chem. Inf. Model..

[13]  H. Gotoh,et al.  Evaluation method of steric shielding effect around nitroxide radical reaction center based on molecular volume within a virtual ball , 2019, Structural Chemistry.

[14]  Xinrui Miao,et al.  Cooperation and competition of hydrogen and halogen bonds in 2D self-assembled nanostructures based on bromine substituted coumarins , 2019, New Journal of Chemistry.

[15]  S. Tsuzuki,et al.  Studies of Halogen Bonding Induced by Pentafluorosulfanyl Aryl Iodides: A Potential Group of Halogen Bond Donors in a Rational Drug Design , 2019, Molecules.

[16]  Diogo Vila-Viçosa,et al.  Halogen bonding in halocarbon-protein complexes and computational tools for rational drug design , 2019, Expert opinion on drug discovery.

[17]  Nicolas K. Shinada,et al.  Halogens in Protein-Ligand Binding Mechanism: A Structural Perspective. , 2019, Journal of medicinal chemistry.

[18]  D. Quiñonero,et al.  Hydrogen Bond versus Halogen Bond in HXOn (X = F, Cl, Br, and I) Complexes with Lewis Bases , 2019, Inorganics.

[19]  Bani Kanta Sarma,et al.  Relative orientation of the carbonyl groups determines the nature of orbital interactions in carbonyl–carbonyl short contacts , 2018, Chemical science.

[20]  A. Masunov,et al.  Toward First-Principles Design of Organic Nonlinear Optical Materials: Crystal Structure Prediction and Halogen Bonding Impact on Hyperpolarizabilities of 2-Iodo-3-hydroxypyridine , 2018, Crystal Growth & Design.

[21]  Sanna P. Niinivehmas,et al.  Blocking oestradiol synthesis pathways with potent and selective coumarin derivatives , 2018, Journal of enzyme inhibition and medicinal chemistry.

[22]  J. Murray,et al.  The σ-hole revisited. , 2017, Physical chemistry chemical physics : PCCP.

[23]  P. S. Ho,et al.  Relationships between hydrogen bonds and halogen bonds in biological systems. , 2017, Acta crystallographica Section B, Structural science, crystal engineering and materials.

[24]  C. Draghici,et al.  Reaction of 4-hydroxycoumarin or its O-substituted derivatives with diatomic interhalogens: ICl and IBr , 2017 .

[25]  I. Bruno,et al.  Cambridge Structural Database , 2002 .

[26]  J. Halpert,et al.  Coumarin Derivatives as Substrate Probes of Mammalian Cytochromes P450 2B4 and 2B6: Assessing the Importance of 7-Alkoxy Chain Length, Halogen Substitution, and Non-Active Site Mutations. , 2016, Biochemistry.

[27]  Pavel Hobza,et al.  Computer Modeling of Halogen Bonds and Other σ-Hole Interactions. , 2016, Chemical reviews.

[28]  Pierangelo Metrangolo,et al.  The Halogen Bond , 2016, Chemical reviews.

[29]  P. Kamath,et al.  Some new indole-coumarin hybrids; Synthesis, anticancer and Bcl-2 docking studies. , 2015, Bioorganic chemistry.

[30]  Jalal Soubhye,et al.  Halogen bonding in polymer science: from crystal engineering to functional supramolecular polymers and materials , 2015 .

[31]  G. Sheldrick.  Crystal structure refinement with SHELXL , 2015, Acta crystallographica. Section C, Structural chemistry.

[32]  Xiang Li,et al.  The antioxidant methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate. , 2014, Acta crystallographica. Section C, Structural chemistry.

[33]  Enzo Cadoni,et al.  Halogen and Hydrogen Bonding Benzothiophene Diol Derivatives: A Study Using ab initio Calculations and X-Ray Crystal Structure Measurements , 2014, ChemistryOpen.

[34]  William L. Jorgensen,et al.  The many faces of halogen bonding: a review of theoretical models and methods , 2014 .

[35]  G. Desiraju,et al.  Halogen bonds in crystal engineering: like hydrogen bonds yet different. , 2014, Accounts of chemical research.

[36]  Christophe M. L. Vande Velde,et al.  Interplay between Halogen Bonding and Lone Pair-π Interactions: A Computational and Crystal Packing Study. , 2014, ChemPlusChem.

[37]  C. Jelsch,et al.  The enrichment ratio of atomic contacts in crystals, an indicator derived from the Hirshfeld surface analysis , 2014, IUCrJ.

[38]  P. Metrangolo,et al.  Type II halogen···halogen contacts are halogen bonds , 2013, IUCrJ.

[39]  Suman Sirimulla,et al.  Halogen Interactions in Protein-Ligand Complexes: Implications of Halogen Bonding for Rational Drug Design , 2013, J. Chem. Inf. Model..

[40]  G. Desiraju,et al.  Halogen bonds in some dihalogenated phenols: applications to crystal engineering , 2013, IUCrJ.

[41]  A. V. D. Lee.  Charge flipping for routine structure solution , 2013 .

[42]  Tjelvar S. G. Olsson,et al.  Evaluation of molecular crystal structures using Full Interaction Maps , 2013 .

[43]  Pierangelo Metrangolo,et al.  Definition of the halogen bond (IUPAC Recommendations 2013) , 2013 .

[44]  M. Chudziński,et al.  Halogen bonding in solution: thermodynamics and applications. , 2013, Chemical Society reviews.

[45]  L. P. Wolters,et al.  Halogen Bonding versus Hydrogen Bonding: A Molecular Orbital Perspective , 2012, ChemistryOpen.

[46]  G. Cavallo,et al.  Self-Complementary Nonlinear Optical-Phores Targeted to Halogen Bond-Driven Self-Assembly of Electro-Optic Materials , 2011 .

[47]  Richard I. Cooper,et al.  CRYSTALS enhancements: dealing with hydrogen atoms in refinement , 2010 .

[48]  Weiliang Zhu,et al.  Nonbonding interactions of organic halogens in biological systems: implications for drug discovery and biomolecular design. , 2010, Physical chemistry chemical physics : PCCP.

[49]  S. Grimme,et al.  A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. , 2010, The Journal of chemical physics.

[50]  Richard J. Gildea,et al.  OLEX2: a complete structure solution, refinement and analysis program , 2009 .

[51]  Dylan Jayatilaka,et al.  Hirshfeld surface analysis , 2009 .

[52]  P. Beer,et al.  Halogen Bonding in Supramolecular Chemistry. , 2008, Chemical reviews.

[53]  J. Reedijk,et al.  Lone pair–π interactions: a new supramolecular bond? , 2008 .

[54]  C. Aakeröy,et al.  Structural competition between hydrogen bonds and halogen bonds. , 2007, Journal of the American Chemical Society.

[55]  F. Weigend,et al.  Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy. , 2005, Physical chemistry chemical physics : PCCP.

[56]  D. Power,et al.  High Resolution Crystal Structures of Piscine Transthyretin Reveal Different Binding Modes for Triiodothyronine and Thyroxine* , 2004, Journal of Biological Chemistry.

[57]  P. Metrangolo,et al.  Hybrid iodoperfluoroalkane-ferrocene supramolecular arrays: the shortest contacts iodine forms with nitrogen atoms and unsaturated moieties , 2004 .

[58]  Richard I. Cooper,et al.  CRYSTALS version 12: software for guided crystal structure analysis , 2003 .

[59]  G. Schussler,et al.  Thyroxine-binding proteins. , 2000, Thyroid : official journal of the American Thyroid Association.

[60]  Robin Taylor,et al.  IsoStar: A library of information about nonbonded interactions , 1997, J. Comput. Aided Mol. Des..

[61]  V. Bertolasi,et al.  Resonance‐Assisted O‐H ⃛ O Hydrogen Bonding: Its Role in the Crystalline Self‐Recognition of β‐Diketone Enols and its Structural and IR Characterization , 1996 .

[62]  A. Becke.  Density-functional thermochemistry. III. The role of exact exchange , 1993 .

[63]  Dennis R. Salahub,et al.  Optimization of Gaussian-type basis sets for local spin density functional calculations. Part I. Boron through neon, optimization technique and validation , 1992 .

[64]  Parr,et al.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. , 1988, Physical review. B, Condensed matter.

[65]  Cheng Chang,et al.  Properties of atoms in molecules: atomic volumes , 1987 .

[66]  C. A. Tolman,et al.  Steric effects of phosphorus ligands in organometallic chemistry and homogeneous catalysis , 1977 .

[67]  J. Gaultier,et al.  Structure de l'hydroxy‐4‐coumarine. Eau d'hydratation et cohésion cristalline , 1966 .

[68]  J. Gaultier,et al.  Structure cristalline et moléculaire de la bromo‐3‐hydroxy‐4‐coumarine monohydraté , 1965 .

[69]  J. Bernal,et al.  Thyroid hormone transporters—functions and clinical implications , 2015, Nature Reviews Endocrinology.

[70]  M. Kolář,et al.  The strength and directionality of a halogen bond are co-determined by the magnitude and size of the σ-hole. , 2014, Physical chemistry chemical physics : PCCP.

[71]  A. Rajbanshi,et al.  Supramolecular synthesis based on a combination of hydrogen- and halogen bonds. , 2009, Crystal growth & design.

[72]  T. G. Denisova,et al.  Reactivity of nitroxyl radicals in reactions with phenols, amines and thiophenols , 1997 .

[73]  T. Komatsuzaki,et al.  A new method for evaluating the steric hindrance by substituent , 1989 .

[74]  Peter Murray-Rust,et al.  Angular preferences of intermolecular forces around halogen centers: preferred directions of approach of electrophiles and nucleophiles around carbon-halogen bond , 1986 .

[75]  K. P. Link,et al.  Studies on 4-Hydroxycoumarin. VII. Reactions of 4-Hydroxycoumarin with Cationoid Reagents1 , 1945 .

[76]  Stromeyer.  Ein sehr empsindliches Reagens fr Jodine, aufgefunden in der Strke (Amidon) , 1815 .