A single crystal X-ray study of the products of halogen mercury cyclization of 8-allylthioquinoline

Слепухин, П. А.; Batalov, V. I.; Kim, D. G.; Charushin, Valery N.

doi:10.1134/s0022476612010192

Cited by 7 publications

(4 citation statements)

References 5 publications

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“…Hg–N distances are in the range 2.501–3.498 Å (based on CSD search) found for mercury and pyridine/pyrazine complexes − except for complex 1 where Hg–N 2.174(6) Å is significantly and surprisingly shorter and is attributed to the linear C16–H16C···N1(py) (Figure S2, Table S4, SI) along the a axis. Since the coordination through N1 is also propagating the chains along the a axis, the hydrogen bonding contact acts cooperatively to bring N(py) closer to Hg(II).…”

Section: Discussionmentioning

confidence: 93%

First Report on Crystal Engineering of Hg(II) Halides with Fully Substituted 3,4-Pyridinedicarboxamides: Generation of Two-Dimensional Coordination Polymers and Linear Zig-Zag Chains of Mercury Metal Ions

Rana

Sharma

Hundal

2015

Crystal Growth & Design

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Two new ligands N,N,N′,N′-tetraisopropyl/tetraisobutyl-3,4-pyridinedicarboxamide L1-L2 and six of their Hg(II)X 2 complexes (where X= Cl -, Br -and I -) have been synthesized and characterized. Single crystal X-ray structures of three complexes of L1 (1-3) with HgCl 2 /Br 2 / I 2 and two complexes of L2 (4-5) with HgCl 2 /Br 2 , show that these are 2D coordination polymers, with three different (one new) topologies and five coordinated Hg(II) ions, in square pyramidal coordination. Complex 6, of L2 with HgI 2 , is a dimer with a four coordinated tetrahedral Hg(II) ion. The ligands behave as 2-or 3-connecting linkers for forming CPs but only 1-connector in the dimer. Various types of H-bonding and other noncovalent interactions have been calculated, analyzed and discussed for all the complexes and the ligand L1. Though large size and soft character of iodide coupled with the steric effects of large isobutyl groups, are mainly responsible for a change in the primary structure of 6, but a significant role of the semilocalized LP···π and C-H···O non-covalent interactions into this has also been found. The latter transform this dimer to a stable 2D H-bonded network instead of a coordination polymer. The unique halide bridged 2D structure of 1 forms 1D zig-zag chains of metal ions owing to the mercurophilic interactions. Weaker interactions of the same kind further extend along the basic skeleton of 2D CP and are facilitated by LP···π, strong C-H···Cl and C-H···N(py) interactions.

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Section: Discussionmentioning

confidence: 93%

First Report on Crystal Engineering of Hg(II) Halides with Fully Substituted 3,4-Pyridinedicarboxamides: Generation of Two-Dimensional Coordination Polymers and Linear Zig-Zag Chains of Mercury Metal Ions

Rana

Sharma

Hundal

2015

Crystal Growth & Design

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“…Anumber of syntheses for 8-thioquinoline compounds with fused N-1/C-8 centers [3][4][5] werereported. Represented crystal structure can be aconvenient model for studying cation×××triiodide anion interactions [6][7] as it illustrates I×××Inon-covalent interactions involving terminal triiodide atomsa sd onors of electrons and iodine atom in =C12-I1 group as electron acceptor.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (E)-3-(1-iodoethylidene)-2,3-dihydro-[1,4]thiazino- [2,3,4-ij]quinolin-4-ium triiodide, C13H11I4NS

Batalov

Dikhtiarenko

Yushina

et al. 2014

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of material 8-(But-2-yn-1-ylthio)quinoline was prepared by method described in [3] from sodium 8-quinolinethiolate with 1-bromobut-2-yne as alkylating agent. The title compound was synthesized by the reaction of 8-(but-2-yn-1-ylthio)quinoline with iodine. The solutions of iodine( 0.381g ,1 .5 mmol) and 8-(but-2-yn-1-ylthio)-quinoline (0.107 g, 0.5mmol) in dichloromethane (10 ml) were mixed. Single crystals for the X-ray diffraction study were obtained after keeping the resulting mixture at room temperature in closed flask for 48 hours, yield: 0.447 g(55 %). Experimental detailsPosition of theHatoms were calculated basedongeometric criteria (C-H =0.96 Åand 0.93 Åfor methyl and aromatic atoms, respectively) than have been placed in their calculated position and refined isotropically using ar iding modelw ith U iso (H) =1 .5 U eq (C) for methyl and U iso (H) =1.2 U eq (C) forall others. DiscussionTricyclic quinoline based systems, including sulfur-containing derivatives, are known as effective antibiotics [1-2]. Anumber of syntheses for 8-thioquinoline compounds with fused N-1/C-8 centers [3][4][5] werereported. Represented crystal structure can be aconvenient model for studying cation×××triiodide anion interactions [6][7] as it illustrates I×××Inon-covalent interactions involving terminal triiodide atomsa sd onors of electrons and iodine atom in =C12-I1 group as electron acceptor. This type of interactions can be attributed to halogen bonding [8].The asymmetric unit of title structure consists of one quinolinium derivative cation [C 13 H 11 INS] + and one triiodide anion. The six-membered ring, formeda st he result of cyclization process, deviates from planarity. TheC10 atom of methylene group is significantly out of plane (16.4°). Molecular conformation is stabilized by intramolecular contacts C13-H13c×××N1' (D×××Adistance of 2.957(7) Å; '=x,y,z), C10-H10b×××I1' (D×××Ad istance of 3.362(6) Å; '= x,y,z)a nd C13-H13A×××I1' (D×××Ad istance of 3.036(7) Å; '= x,y,z). The triiodide anion is symmetric and nearly linear with I2-I3 and I3-I4 distances of 2.9130(7) Åa nd 2.9114(7) Å; the I2-I3-I4 angle of 177.97(2)°. Terminal atom of triiodide involved in the short contact with iodine of =C12-I1 group: I4×××I1' (' =-x+2,y,-z+½; distance is 3.6988(6) Å, angle is close to right angle (82.62°)). This I×××Id istance is slightly longer than those values reported for triiodide -t riiodide interactions [9]. The triiodide anion is situated near the organic cation so that central I6 atom is locatedoverthe center of the p-system with centroid×××I3 distances of 3.81 Å. The axis of triiodide anions is inclined on 25.7°in respect to the plane of quinolinium ring. This mutual orientation is aresultofcharge-transfer interactions which favor location of iodide donor orbital toward the nitrogen or adjacent carbon of quinolinium rings. Aparticularly interesting feature of crystal packing is the formation of dimeric structural motifs represented by [C 13 H 11 INS] + organic cations and triiodide anions linked via C10-H10B×××I4' (H×...

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“…Thepresented crystalstructure canbeaninteresting object with I×××In on-covalent interactions involving terminal triiodide atomsasdonors of electrons and iodine in I 2 molecule as electrophilic species. This type of interactions refers to halogen bonding [3][4][5][6][7][8][9][10]. The asymetric unit of the title compound consists of quinolinium derivative cation, triiodide anion and half of molecular iodine.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (E)-3-(iodomethylene)-2,3-dihydro-[1,4]oxazino- [2,3,4-ij]quinolin-4-ium triodide —iodine (2:1), [C12H9INO]I3·0.5I2, C12H9I5NO

Batalov

Kim

Dikhtiarenko

et al. 2014

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of material 8-(propargyloxy)quinoline was obtained by the reaction of 8-quinolinol with propargylbromide in acetone/K 2 CO 3 with reflux. Asolutionof8-(propargyloxy)quinoline (0.145g,1mmol) in 5 mL of dichloromethane wasm ixed with 0.762 go fi odine( 3 mmol) in 15 mL of dichloromethane. Dark purplesingle crystals for the X-ray diffraction study were obtained after keeping the mixture at room temperatureinclosed flask for 48 hours, yield: 0.447 g(55 %). Experimental detailsPosition of theHatoms were calculated based on geometric criteria(C-H=0.97 Å, 0.93 Åand 0.85 Åfor methylene, aromatic and methine atoms,respectively)than have been placed in their calculatedposition andrefined isotropicallyusing arider modelwith U iso (H)=1.2U eq (C). The resulting six-membered ring is partially planar, where the C10 atom of the methylene group is slightly out of plane. The crystal structure confirms the closure of the ring between O1 and N1 atoms, where formed C11-N1 bond is covalent (1.451(5) Å).T he C11-C12 bond, that is associated with sixmember ring, has double bond character with abond distance of 1.324(6) Å. TheC12-I1 bond (2.082(4) Å) significantly deviated from mean plane of quinolinium moiety, the C11-C12-I1 angle is 123.6(3)°. Crystal packing is formedbymultiple interactions of [C 12 H 9 INO] + cations, triiodide and iodine molecules. Theorganic cationspackcould be represented as the dimeric association establishedbyap-p interaction.The fusedrings aresituated in opposite directions and lie nearly parallel to oneanother;the closest centroid-centroidd istance is 3.51(6)Å .T he dimers ares urroundedbytriiodide anions and iodine molecules. The geometry of triiodide is almost linear, I2-I3 and I3-I4 distancesa re Z. Kristallogr. Discussion

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A single crystal X-ray study of the products of halogen mercury cyclization of 8-allylthioquinoline

Abstract: The reaction products of 8-allylthioquinoline with mercury halides are studied by single crystal X-ray diffraction. It is shown that the products are organomercury derivatives of salts of 2,3-dihydro[1,4]-thiazino[2,3,4-ij]quinoliniuim.

Cited by 7 publications

References 5 publications

First Report on Crystal Engineering of Hg(II) Halides with Fully Substituted 3,4-Pyridinedicarboxamides: Generation of Two-Dimensional Coordination Polymers and Linear Zig-Zag Chains of Mercury Metal Ions

First Report on Crystal Engineering of Hg(II) Halides with Fully Substituted 3,4-Pyridinedicarboxamides: Generation of Two-Dimensional Coordination Polymers and Linear Zig-Zag Chains of Mercury Metal Ions

Crystal structure of (E)-3-(1-iodoethylidene)-2,3-dihydro-[1,4]thiazino- [2,3,4-ij]quinolin-4-ium triiodide, C13H11I4NS

Crystal structure of (E)-3-(iodomethylene)-2,3-dihydro-[1,4]oxazino- [2,3,4-ij]quinolin-4-ium triodide —iodine (2:1), [C12H9INO]I3·0.5I2, C12H9I5NO

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