01763nas a2200241 4500008004100000022001400041245014500055210006900200260007300269300001200342490000800354520083600362653002101198653001601219653002201235653002001257100002401277700002101301700002401322700002201346700002501368856012801393 2008 eng d a0022-286000aMolecular association via halogen bonding and other weak interactions in the crystal structures of 11-bromo-12-oxo-5 beta-cholan derivatives0 aMolecular association via halogen bonding and other weak interac aPO BOX 211, 1000 AE AMSTERDAM, NETHERLANDSbELSEVIER SCIENCE BVcDEC a246-2530 v8923 a

Methyl 3 alpha,7 alpha-diacetoxy-12-oxo-5 beta-cholan-24-oate 2, methyl 11 alpha-bromo-3 alpha,7 alpha-diacetoxy-12-oxo-5 beta-cholan-24-oate 3, methyl 11 beta-bromo-3 alpha,7 alpha-diacetoxy-12-oxo-5 beta-cholan-24-oate 4 and methyl 11,11-dibromo-3 alpha,7 alpha-diacetoxy-12-oxo-5 beta-cholan-24-oate 5 were synthesized. The crystal structures of these molecules were resolved to study the effect of bulky bromine atom in the steroid skeleton of cholic acid with different stereo-chemical orientations at C-11 on the two-dimensional arrangement of molecules and solid-state properties. All the molecules associate only via weak intermolecular interactions in their crystal structures, notable one being the Halogen Bonded assembly (C-Br center dot center dot center dot O) in 5. (C) 2008 Elsevier B.V. All rights reserved.

10a11-Bromosteroids10aCholic acid10acrystal structure10aHalogen bonding1 aSalunke, Deepak, B.1 aHazra, Braja, G.1 aGonnade, Rajesh, G.1 aPore, Vandana, S.1 aBhadbhade, Mohan, M. uhttp://library.ncl.res.in/content/molecular-association-halogen-bonding-and-other-weak-interactions-crystal-structures-11-001687nas a2200265 4500008004100000022001400041245010200055210006900157260005700226300001200283490000700295520075000302653001701052653002201069653002501091653001301116653003001129653001701159653003001176100002401206700002401230700002501254700002301279856011901302 2010 eng d a0022-476600aConformational polymorphism in racemic 2,4-Di-o-Benzoyl-6-o-Tosyl myo-Inositol 1,3,5-Orthoacetate0 aConformational polymorphism in racemic 24DioBenzoyl6oTosyl myoIn a233 SPRING ST, NEW YORK, NY 10013 USAbSPRINGERcAUG a725-7300 v513 a

The title compound, C(29)H(26)O(10)S, yields two conformational polymorphs concomitantly from dichloromethane-methanol mixture; the major polymorph grows as plates (Form I, monoclinic, P2(1)/n) and the minor polymorph grows as needles (Form II, triclinic, P-1). The two forms differ mainly in orientation of the tosyl group. In Form I, sulfonyl oxygen of the tosyl group makes intermolecular C -HaEuro broken vertical bar O interactions, whereas the same group in Form II is involved in an intramolecular short dipolar S=OaEuro broken vertical bar C=O (sulfonyl-carbonyl) contact. The molecular organization and the influence of various weak non-covalent interactions that stabilize these conformers in the crystal lattices are discussed.

10aConformation10acrystal structure10adipolar interactions10aInositol10anon-covalent interactions10apolymorphism10asulfonyl-carbonyl contact1 aManoj, Kochunnoonny1 aGonnade, Rajesh, G.1 aBhadbhade, Mohan, M.1 aShashidhar, M., S. uhttp://library.ncl.res.in/content/conformational-polymorphism-racemic-24-di-o-benzoyl-6-o-tosyl-myo-inositol-135-002436nas a2200277 4500008004100000022001400041245017600055210006900231260006700300300001000367490000700377520139300384653001801777653001401795653002201809653003201831653002101863653002101884653001701905653002601922100002301948700001701971700002401988700002702012856011902039 2014 eng d a0108-270100aCorrelation of the solid-state reactivities of racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate and its 4,4 `-bipyridine cocrystal with their crystal structures0 aCorrelation of the solidstate reactivities of racemic 246diObenz a111 RIVER ST, HOBOKEN 07030-5774, NJ USAbWILEY-BLACKWELLcNOV a1040+0 v703 a

Racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate, C21H18O8, (1), shows a very efficient intermolecular benzoyl-group migration reaction in its crystals. However, the presence of 4,4 `-bipyridine molecules in its cocrystal, C21H18O8 center dot C10H8N2, (1)center dot BP, inhibits the intermolecular benzoyl-group transfer reaction. In (1), molecules are assembled around the crystallographic twofold screw axis (b axis) to form a helical self-assembly through conventional O-H center dot center dot center dot O hydrogen-bonding interactions. This helical association places the reactive C6-O-benzoyl group (electrophile, El) and the C4-hydroxy group (nucleophile, Nu) in proximity, with a preorganized El center dot center dot center dot Nu geometry favourable for the acyl transfer reaction. In the cocrystal (1)center dot BP, the dibenzoate and bipyridine molecules are arranged alternately through OH center dot center dot center dot N interactions. The presence of the bipyridine molecules perturbs the regular helical assembly of the dibenzoate molecules and thus restricts the solid-state reactivity. Hence, unlike the parent dibenzoate crystals, the cocrystals do not exhibit benzoyl-transfer reactions. This approach is useful for increasing the stability of small molecules in the crystalline state and could find application in the design of functional solids.

10aacyl transfer10acocrystal10acrystal structure10adesign of functional solids10ahelical assembly10ahydrogen bonding10amyo-inositol10asolid-state reactions1 aTamboli, Majid, I.1 aBahadur, Vir1 aGonnade, Rajesh, G.1 aShashidhar, Mysore, S. uhttp://library.ncl.res.in/content/correlation-solid-state-reactivities-racemic-246-di-o-benzoyl-myo-inositol-135-004389nas a2200265 4500008004100000022001400041245017900055210006900234260007400303300001400377490000700391520332100398653003003719653004303749653001403792653002203806653002103828653002603849653002303875653002803898100002503926700002403951700002403975856012403999 2015 eng d a2053-229600aCrystal structures of the pyrazinamide-p-aminobenzoic acid (1/1) cocrystal and the transamidation reaction product 4-(pyrazine-2-carboxamido)-benzoic acid in the molten state0 aCrystal structures of the pyrazinamidepaminobenzoic acid 11 cocr a2 ABBEY SQ, CHESTER, CH1 2HU, ENGLANDbINT UNION CRYSTALLOGRAPHYcNOV a1010-U2760 v713 a

The synthesis of pharmaceutical cocrystals is a strategy to enhance the performance of active pharmaceutical ingredients (APIs) without affecting their therapeutic efficiency. The 1: 1 pharmaceutical cocrystal of the antituberculosis drug pyrazinamide (PZA) and the cocrystal former p-aminobenzoic acid (p-ABA), C7H7NO2- C5H5N3O, (1), was synthesized successfully and characterized by relevant solid-state characterization methods. The cocrystal crystallizes in the monoclinic space group P21/n containing one molecule of each component. Both molecules associate via intermolecular O-H center dot center dot center dot O and NH center dot center dot center dot O hydrogen bonds [O center dot center dot center dot O = 2.6102 (15)angstrom and O-H center dot center dot center dot O = 168.3 (19)degrees; N center dot center dot center dot O = 2.9259 (18) angstrom and N-H center dot center dot center dot O = 167.7 (16)degrees] to generate a dimeric acidamide synthon. Neighbouring dimers are linked centrosymmetrically through N-H center dot center dot center dot O interactions [N center dot center dot center dot O = 3.1201 (18) angstrom and N-H center dot center dot center dot O = 136.9 (14)degrees] to form a tetrameric assembly supplemented by C-H center dot center dot center dot N interactions [C center dot center dot center dot N = 3.5277 (19) angstrom and C-H center dot center dot center dot N = 147 degrees]. Linking of these tetrameric assemblies through N-H center dot center dot center dot O [N center dot center dot center dot O = 3.3026 (19) angstrom and N-H center dot center dot center dot O = 143.1 (17)degrees], NH center dot center dot center dot N [N center dot center dot center dot N = 3.221 (2) angstrom and N-H center dot center dot center dot N = 177.9 (17)degrees] and C-H center dot center dot center dot O [C center dot center dot center dot O = 3.5354 (18) angstrom and C-H center dot center dot center dot O = 152 degrees] interactions creates the twodimensional packing. Recrystallization of the cocrystals from the molten state revealed the formation of 4-(pyrazine-2-carboxamido) benzoic acid, C12H9N3O3, (2), through a transamidation reaction between PZA and p-ABA. Carboxamide (2) crystallizes in the triclinic space group P1 with one molecule in the asymmetric unit. Molecules of (2) form a centrosymmetric dimeric homosynthon through an acid-acid O-H center dot center dot center dot O hydrogen bond [O center dot center dot center dot O = 2.666 (3) angstrom and O-H center dot center dot center dot O = 178 (4) degrees]. Neighbouring assemblies are connected centrosymmetrically via a C-H center dot center dot center dot N interaction [C center dot center dot center dot N = 3.365 (3) angstrom and C-H center dot center dot center dot N = 142 degrees] engaging the pyrazine groups to generate a linear chain. Adjacent chains are connected loosely via C-H center dot center dot center dot O interactions [C center dot center dot center dot O = 3.212 (3) angstrom and CH center dot center dot center dot O = 149 degrees] to generate a two-dimensional sheet structure. Closely associated two-dimensional sheets in both compounds are stacked via aromatic pi-stacking interactions engaging the pyrazine and benzene rings to create a threedimensional multi-stack structure.

10aacid-amide hetero-synthon10aactive pharmaceutical ingredient (API)10acocrystal10acrystal structure10ahydrogen bonding10amolten-state reaction10apowder diffraction10atransamidation reaction1 aThorat, Shridhar, H.1 aSahu, Sanjay, Kumar1 aGonnade, Rajesh, G. uhttp://library.ncl.res.in/content/crystal-structures-pyrazinamide-p-aminobenzoic-acid-11-cocrystal-and-transamidation-102734nas a2200313 4500008004100000022001400041245014500055210006900200260006700269300001400336490000800350520162500358653002401983653001502007653002402022653002202046653002102068653001202089653002102101653001502122653001402137653002102151100002502172700002402197700002802221700002502249700002402274856012202298 2015 eng d a0022-354900aDrug-drug molecular salt hydrate of an anticancer drug gefitinib and a loop diuretic drug furosemide: an alternative for multidrug treatment0 aDrugdrug molecular salt hydrate of an anticancer drug gefitinib  a111 RIVER ST, HOBOKEN 07030-5774, NJ USAbWILEY-BLACKWELLcDEC a4207-42160 v1043 a

A 1:1 monohydrate salt containing gefitinib, an orally administrated chemotherapy treatment for lung and breast cancers and furosemide, a loop diuretic drug, commonly used in the treatment of hypertension and edema, has been prepared. The molecular salt crystallized in triclinic P-1 space group. The CO bond lengths (similar to 1.26 angstrom) in the COOH group show that proton transfer has occurred from furosemide to morpholine moiety of the gefitinib suggesting cocrystal to be ionic. The morpholine moiety of the gefitinib showed significant conformational change because of its involvement in conformation dictating the strong N-H center dot center dot center dot O hydrogen bonding interaction. The strong hydrogen bonding interaction between gefitinib and furosemide places their benzene rings in stacking mode to facilitate the generation of pi-stack dimers. The neighboring dimers are bridged to each other via water molecule through N-H center dot center dot center dot O, C-H center dot center dot center dot O, O-H center dot center dot center dot N, and O-H center dot center dot center dot O interactions. The remarkable stability of the salt hydrate could be attributed to the strong hydrogen bonding interactions in the crystal structure. Interestingly, release of water from the lattice at 140 degrees C produced new anhydrous salt that has better solubility and dissolution rate than salt hydrate. The drug-drug molecular salt may have some bearing on the treatment of patient suffering from anticancer and hypertension. (C) 2015 Wiley Periodicals, Inc. and the American Pharmacists Association

10acancer chemotherapy10acocrystals10acrystal engineering10acrystal structure10adissolution rate10ahydrate10aphase transition10asolubility10astability10athermal analysis1 aThorat, Shridhar, H.1 aSahu, Sanjay, Kumar1 aPatwadkar, Manjusha, V.1 aBadiger, Manohar, V.1 aGonnade, Rajesh, G. uhttp://library.ncl.res.in/content/drug-drug-molecular-salt-hydrate-anticancer-drug-gefitinib-and-loop-diuretic-drug-001480nas a2200253 4500008004100000022001400041245010900055210006900164260000800233300000900241490000700250520061800257653002200875653002200897653002900919653002000948653001200968100002200980700002401002700002601026700002401052700002401076856012601100 2020 eng d a2053-229600aInfluence of fluorine substitution on the molecular conformation of 3 `-deoxy-3 `-fluoro-5-methyluriaine0 aInfluence of fluorine substitution on the molecular conformation cAPR a346+0 v763 a

{Fluorine substitutions on the furanose ring of nucleosides are known to strongly influence the conformational properties of oligonucleotides. In order to assess the effect of fluorine on the conformation of 3'-deoxy-3'-fluoro-5-methyluridine (T-R(F)), C-10 H13FN2O5, we studied its stereochemistry in the crystalline state using X-ray crystallography. The compound crystallizes in the chiral orthorhombic space group P2(1)2(1)2(1) and contains two symmetry-independent molecules (A and B) in the asymmetric unit. The furanose ring in molecules A and B adopts conformations between envelope (E-2, 2'-endo

10acrystal structure10afluoro nucleoside10apseudorotation parameter10asugar puckering10auridine1 aAher, Manisha, N.1 aErande, Namrata, D.1 aKumar, Vaijayanti, A.1 aFernandes, Moneesha1 aGonnade, Rajesh, G. uhttp://library.ncl.res.in/content/influence-fluorine-substitution-molecular-conformation-3-deoxy-3-fluoro-5-methyluriaine