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A novel class of naturally occurring halogenated pyrroles, 1,1′-dimethyl-3,3′,4,4′,5,5′-hexabromo-2,2′-bipyrrole, 5,5′-dichloro-1,1′-dimethyl-3,3′,4,4′-tetrabromo-2,2′-bipyrrole, and 1,1′-dimethyl-3,3′,4,4′,5,5′-hexachloro-2,2′-bipyrrole

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Abstract

Crystal structure determinations of the three title hexahalogenated bipyrroles, (I) C10H6Br6N2, (II) C10H6Br4Cl2N2, and (III) C10H6Cl6N2, reveal essentially planar pyrrole rings having dihedral angles of 64.7, 65.1, and 64.2° between the least-squares planes, favoring in each case a closer methyl–halogen conformation. All three complexes crystallize in the orthorhombic space group Pbcn with the following cell dimensions: (I) a = 12.654(3) Å, b = 8.853(2) Å, c = 13.753(3) Å, α = β = γ = 90°, Z = 4; (II) a = 12.438(6) Å, b = 8.753(6) Å, c = 13.696(3) Å, α = β = γ = 90°, Z = 4; (III) a = 12.088(6) Å, b = 8.566(4) Å, c = 13.486(8) Å, α = β = γ = 90°, Z = 4.

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Authors and Affiliations

  1. Department of Chemistry, Dartmouth College, Hanover, New Hampshire, 03755-3564

    David H. Blank, Gordon W. Gribble & John S. Schneekloth Jr.

  2. Department of Chemistry, Keene State College, 229 Main Street Keene, New Hampshire, 03435-2001

    Jerry P. Jasinski

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  1. David H. Blank
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  2. Gordon W. Gribble
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  3. John S. Schneekloth Jr.
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  4. Jerry P. Jasinski
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Correspondence to Jerry P. Jasinski.

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Blank, D.H., Gribble, G.W., Schneekloth, J.S. et al. A novel class of naturally occurring halogenated pyrroles, 1,1′-dimethyl-3,3′,4,4′,5,5′-hexabromo-2,2′-bipyrrole, 5,5′-dichloro-1,1′-dimethyl-3,3′,4,4′-tetrabromo-2,2′-bipyrrole, and 1,1′-dimethyl-3,3′,4,4′,5,5′-hexachloro-2,2′-bipyrrole. Journal of Chemical Crystallography 32, 541–546 (2002). https://doi.org/10.1023/A:1021117431367

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