Triclinic and orthorhombic polymorphs of 2-iodo-4-nitroaniline: interplay of hydrogen bonds, nitro center dot center dot center dot I interactions and aromatic pi-pi-stacking interactions

S A McWilliam, J M S Skakle, J N Low, J L Wardell, S J Garden, A C Pinto, J C Torres, C Glidewell

Research output: Contribution to journalArticle

Abstract

In the triclinic polymorph of 2-iodo-4-nitroaniline, C6H5IN2O2, space group P (1) over bar, the molecules are linked by paired N-H . . .O hydrogen bonds into C(8)[R-2(2)(6)] chains of rings. These chains are linked into sheets by nitro . . . I interactions, and the sheets are pairwise linked by aromatic pi-pi -stacking interactions. In the orthorhombic polymorph, space group Pbca, the molecules are linked by single N-H . . .O hydrogen bonds into spiral C(8) chains; the chains are linked by nitro . . . O interactions into sheets, each of which is linked to its two immediate neighbours by aromatic pi-pi -stacking interactions, so producing a continuous three-dimensional structure.

Original languageEnglish
Pages (from-to)942-945
Number of pages4
JournalActa Crystallographica Section C, Crystal Structure Communications
Volume57
Publication statusPublished - 2001

Keywords

  • SUPRAMOLECULAR SYNTHONS
  • CRYSTAL-STRUCTURES

Cite this

Triclinic and orthorhombic polymorphs of 2-iodo-4-nitroaniline: interplay of hydrogen bonds, nitro center dot center dot center dot I interactions and aromatic pi-pi-stacking interactions. / McWilliam, S A ; Skakle, J M S ; Low, J N ; Wardell, J L ; Garden, S J ; Pinto, A C ; Torres, J C ; Glidewell, C .

In: Acta Crystallographica Section C, Crystal Structure Communications, Vol. 57, 2001, p. 942-945.

Research output: Contribution to journalArticle

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abstract = "In the triclinic polymorph of 2-iodo-4-nitroaniline, C6H5IN2O2, space group P (1) over bar, the molecules are linked by paired N-H . . .O hydrogen bonds into C(8)[R-2(2)(6)] chains of rings. These chains are linked into sheets by nitro . . . I interactions, and the sheets are pairwise linked by aromatic pi-pi -stacking interactions. In the orthorhombic polymorph, space group Pbca, the molecules are linked by single N-H . . .O hydrogen bonds into spiral C(8) chains; the chains are linked by nitro . . . O interactions into sheets, each of which is linked to its two immediate neighbours by aromatic pi-pi -stacking interactions, so producing a continuous three-dimensional structure.",
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T1 - Triclinic and orthorhombic polymorphs of 2-iodo-4-nitroaniline: interplay of hydrogen bonds, nitro center dot center dot center dot I interactions and aromatic pi-pi-stacking interactions

AU - McWilliam, S A

AU - Skakle, J M S

AU - Low, J N

AU - Wardell, J L

AU - Garden, S J

AU - Pinto, A C

AU - Torres, J C

AU - Glidewell, C

PY - 2001

Y1 - 2001

N2 - In the triclinic polymorph of 2-iodo-4-nitroaniline, C6H5IN2O2, space group P (1) over bar, the molecules are linked by paired N-H . . .O hydrogen bonds into C(8)[R-2(2)(6)] chains of rings. These chains are linked into sheets by nitro . . . I interactions, and the sheets are pairwise linked by aromatic pi-pi -stacking interactions. In the orthorhombic polymorph, space group Pbca, the molecules are linked by single N-H . . .O hydrogen bonds into spiral C(8) chains; the chains are linked by nitro . . . O interactions into sheets, each of which is linked to its two immediate neighbours by aromatic pi-pi -stacking interactions, so producing a continuous three-dimensional structure.

AB - In the triclinic polymorph of 2-iodo-4-nitroaniline, C6H5IN2O2, space group P (1) over bar, the molecules are linked by paired N-H . . .O hydrogen bonds into C(8)[R-2(2)(6)] chains of rings. These chains are linked into sheets by nitro . . . I interactions, and the sheets are pairwise linked by aromatic pi-pi -stacking interactions. In the orthorhombic polymorph, space group Pbca, the molecules are linked by single N-H . . .O hydrogen bonds into spiral C(8) chains; the chains are linked by nitro . . . O interactions into sheets, each of which is linked to its two immediate neighbours by aromatic pi-pi -stacking interactions, so producing a continuous three-dimensional structure.

KW - SUPRAMOLECULAR SYNTHONS

KW - CRYSTAL-STRUCTURES

M3 - Article

VL - 57

SP - 942

EP - 945

JO - Acta Crystallographica Section C, Crystal Structure Communications

JF - Acta Crystallographica Section C, Crystal Structure Communications

SN - 0108-2701

ER -