Isomers and polymorphs of (E,E)-1,4-bis(nitro-phenyl)-2,3-diaza-1,3-butadienes

C. Glidewell, Janet Mabel Scott Skakle, J. L. Wardell

Research output: Contribution to journalArticle

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Abstract

The structures of five of the possible six isomers of (E, E)1,4-bis(nitrophenyl)-2,3-diaza-1,3-butadiene are reported, including two polymorphs of one of the isomers. (E, E)-1,4Bis(2-nitrophenyl)-2,3-diaza-1,3-butadiene, C14H10N4O4 ( I), crystallizes in two polymorphic forms (Ia) and (Ib) in which the molecules lie across centres of inversion in space groups P2(1)/n and P2(1)/c, respectively: the molecules in (Ia) and (Ib) are linked into chains by aromatic pi (...) pi stacking interactions and C-H (...) pi(arene) hydrogen bonds, respectively. Molecules of (E,E)-1-(2-nitrophenyl)-4-(3-nitrophenyl)-2,3-diaza-1,3-butadiene (II) are linked into sheets by two independent C-H (...) O hydrogen bonds. The molecules of (E, E)-1,4-bis(3-nitrophenyl)- 2,3-diaza-1,3- butadiene (III) lie across inversion centres in the space group P2(1)/n, and a combination of a C-H (...) O hydrogen bond and a pi (...) pi stacking interaction links the molecules into sheets. A total of four independent C H (...) O hydrogen bonds link the molecules of (E, E)-1-(3-nitrophenyl)- 4-(4-nitrophenyl)-2,3-diaza-1,3-butadiene (IV) into sheets. In (E,E)-1,4-bis(4-nitrophenyl)-2,3-diaza-1,3-butadiene (V) the molecules, which lie across centres of inversion in the space group P2(1)/n, are linked by just two independent C-H (...) O hydrogen bonds into a three-dimensional framework.

Original languageEnglish
Pages (from-to)666-675
Number of pages9
JournalActa Crystallographica Section B, Structural Science
Volume62
DOIs
Publication statusPublished - 2006

Keywords

  • PI STACKING INTERACTIONS
  • O HYDROGEN-BONDS
  • CENTER-DOT-NITRO
  • ABSOLUTE-STRUCTURE
  • INTERPLAY
  • PATTERNS

Cite this

Isomers and polymorphs of (E,E)-1,4-bis(nitro-phenyl)-2,3-diaza-1,3-butadienes. / Glidewell, C.; Skakle, Janet Mabel Scott; Wardell, J. L.

In: Acta Crystallographica Section B, Structural Science, Vol. 62, 2006, p. 666-675.

Research output: Contribution to journalArticle

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title = "Isomers and polymorphs of (E,E)-1,4-bis(nitro-phenyl)-2,3-diaza-1,3-butadienes",
abstract = "The structures of five of the possible six isomers of (E, E)1,4-bis(nitrophenyl)-2,3-diaza-1,3-butadiene are reported, including two polymorphs of one of the isomers. (E, E)-1,4Bis(2-nitrophenyl)-2,3-diaza-1,3-butadiene, C14H10N4O4 ( I), crystallizes in two polymorphic forms (Ia) and (Ib) in which the molecules lie across centres of inversion in space groups P2(1)/n and P2(1)/c, respectively: the molecules in (Ia) and (Ib) are linked into chains by aromatic pi (...) pi stacking interactions and C-H (...) pi(arene) hydrogen bonds, respectively. Molecules of (E,E)-1-(2-nitrophenyl)-4-(3-nitrophenyl)-2,3-diaza-1,3-butadiene (II) are linked into sheets by two independent C-H (...) O hydrogen bonds. The molecules of (E, E)-1,4-bis(3-nitrophenyl)- 2,3-diaza-1,3- butadiene (III) lie across inversion centres in the space group P2(1)/n, and a combination of a C-H (...) O hydrogen bond and a pi (...) pi stacking interaction links the molecules into sheets. A total of four independent C H (...) O hydrogen bonds link the molecules of (E, E)-1-(3-nitrophenyl)- 4-(4-nitrophenyl)-2,3-diaza-1,3-butadiene (IV) into sheets. In (E,E)-1,4-bis(4-nitrophenyl)-2,3-diaza-1,3-butadiene (V) the molecules, which lie across centres of inversion in the space group P2(1)/n, are linked by just two independent C-H (...) O hydrogen bonds into a three-dimensional framework.",
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T1 - Isomers and polymorphs of (E,E)-1,4-bis(nitro-phenyl)-2,3-diaza-1,3-butadienes

AU - Glidewell, C.

AU - Skakle, Janet Mabel Scott

AU - Wardell, J. L.

PY - 2006

Y1 - 2006

N2 - The structures of five of the possible six isomers of (E, E)1,4-bis(nitrophenyl)-2,3-diaza-1,3-butadiene are reported, including two polymorphs of one of the isomers. (E, E)-1,4Bis(2-nitrophenyl)-2,3-diaza-1,3-butadiene, C14H10N4O4 ( I), crystallizes in two polymorphic forms (Ia) and (Ib) in which the molecules lie across centres of inversion in space groups P2(1)/n and P2(1)/c, respectively: the molecules in (Ia) and (Ib) are linked into chains by aromatic pi (...) pi stacking interactions and C-H (...) pi(arene) hydrogen bonds, respectively. Molecules of (E,E)-1-(2-nitrophenyl)-4-(3-nitrophenyl)-2,3-diaza-1,3-butadiene (II) are linked into sheets by two independent C-H (...) O hydrogen bonds. The molecules of (E, E)-1,4-bis(3-nitrophenyl)- 2,3-diaza-1,3- butadiene (III) lie across inversion centres in the space group P2(1)/n, and a combination of a C-H (...) O hydrogen bond and a pi (...) pi stacking interaction links the molecules into sheets. A total of four independent C H (...) O hydrogen bonds link the molecules of (E, E)-1-(3-nitrophenyl)- 4-(4-nitrophenyl)-2,3-diaza-1,3-butadiene (IV) into sheets. In (E,E)-1,4-bis(4-nitrophenyl)-2,3-diaza-1,3-butadiene (V) the molecules, which lie across centres of inversion in the space group P2(1)/n, are linked by just two independent C-H (...) O hydrogen bonds into a three-dimensional framework.

AB - The structures of five of the possible six isomers of (E, E)1,4-bis(nitrophenyl)-2,3-diaza-1,3-butadiene are reported, including two polymorphs of one of the isomers. (E, E)-1,4Bis(2-nitrophenyl)-2,3-diaza-1,3-butadiene, C14H10N4O4 ( I), crystallizes in two polymorphic forms (Ia) and (Ib) in which the molecules lie across centres of inversion in space groups P2(1)/n and P2(1)/c, respectively: the molecules in (Ia) and (Ib) are linked into chains by aromatic pi (...) pi stacking interactions and C-H (...) pi(arene) hydrogen bonds, respectively. Molecules of (E,E)-1-(2-nitrophenyl)-4-(3-nitrophenyl)-2,3-diaza-1,3-butadiene (II) are linked into sheets by two independent C-H (...) O hydrogen bonds. The molecules of (E, E)-1,4-bis(3-nitrophenyl)- 2,3-diaza-1,3- butadiene (III) lie across inversion centres in the space group P2(1)/n, and a combination of a C-H (...) O hydrogen bond and a pi (...) pi stacking interaction links the molecules into sheets. A total of four independent C H (...) O hydrogen bonds link the molecules of (E, E)-1-(3-nitrophenyl)- 4-(4-nitrophenyl)-2,3-diaza-1,3-butadiene (IV) into sheets. In (E,E)-1,4-bis(4-nitrophenyl)-2,3-diaza-1,3-butadiene (V) the molecules, which lie across centres of inversion in the space group P2(1)/n, are linked by just two independent C-H (...) O hydrogen bonds into a three-dimensional framework.

KW - PI STACKING INTERACTIONS

KW - O HYDROGEN-BONDS

KW - CENTER-DOT-NITRO

KW - ABSOLUTE-STRUCTURE

KW - INTERPLAY

KW - PATTERNS

U2 - 10.1107/S010876810601439X

DO - 10.1107/S010876810601439X

M3 - Article

VL - 62

SP - 666

EP - 675

JO - Acta Crystallographica Section B, Structural Science

JF - Acta Crystallographica Section B, Structural Science

SN - 0108-7681

ER -