A chain of edge-fused rings generated by the combination of an N-H center dot center dot center dot O hydrogen bond and an iodo-nitro interaction in 2-iodobenzaldehyde 4-nitrophenylhydrazone versus disordered and effectively isolated molecules in 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone

C  Glidewell; J N  Low; J M S  Skakle; J L  Wardell

doi:10.1107/S0108270103001379

A chain of edge-fused rings generated by the combination of an N-H center dot center dot center dot O hydrogen bond and an iodo-nitro interaction in 2-iodobenzaldehyde 4-nitrophenylhydrazone versus disordered and effectively isolated molecules in 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone

C Glidewell, J N Low, J M S Skakle, J L Wardell

Physics

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

Molecules of 2-iodobenzaldehyde 4-nitrophenylhydrazone, C13H10IN3O2, are effectively planar and are linked by an N-H...O hydrogen bond [H...O=2.04 Angstrom, N...O=2.905 (6) Angstrom and NDH...O=166degrees] and a two-centre iodo-nitro interaction [I...O=3.361 (4) Angstrom] into a chain of edge-fused R-3(3) (18) rings. There are no direction-specific interactions between adjacent chains. Molecules of 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone, C13H9IN4O4, are disordered over two orientations with occupancies of 0.681 (5) and 0.319 (5). In the major orientation, there are no direction-specific intermolecular interactions, while for the minor form, a single C-H...O hydrogen bond generates centrosymmetric dimers.

Original language	English
Pages (from-to)	o98-o101
Number of pages	4
Journal	Acta Crystallographica Section C, Crystal Structure Communications
Volume	C59
DOIs	https://doi.org/10.1107/S0108270103001379
Publication status	Published - 2003

Keywords

pi-stacking interactions
interlay

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Glidewell, C., Low, J. N., Skakle, J. M. S., & Wardell, J. L. (2003). A chain of edge-fused rings generated by the combination of an N-H center dot center dot center dot O hydrogen bond and an iodo-nitro interaction in 2-iodobenzaldehyde 4-nitrophenylhydrazone versus disordered and effectively isolated molecules in 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone. Acta Crystallographica Section C, Crystal Structure Communications, C59, o98-o101. https://doi.org/10.1107/S0108270103001379

A chain of edge-fused rings generated by the combination of an N-H center dot center dot center dot O hydrogen bond and an iodo-nitro interaction in 2-iodobenzaldehyde 4-nitrophenylhydrazone versus disordered and effectively isolated molecules in 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone. / Glidewell, C ; Low, J N ; Skakle, J M S et al.

In: Acta Crystallographica Section C, Crystal Structure Communications, Vol. C59, 2003, p. o98-o101.

Research output: Contribution to journal › Article › peer-review

Glidewell, C, Low, JN, Skakle, JMS & Wardell, JL 2003, 'A chain of edge-fused rings generated by the combination of an N-H center dot center dot center dot O hydrogen bond and an iodo-nitro interaction in 2-iodobenzaldehyde 4-nitrophenylhydrazone versus disordered and effectively isolated molecules in 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone', Acta Crystallographica Section C, Crystal Structure Communications, vol. C59, pp. o98-o101. https://doi.org/10.1107/S0108270103001379

Glidewell C, Low JN, Skakle JMS, Wardell JL. A chain of edge-fused rings generated by the combination of an N-H center dot center dot center dot O hydrogen bond and an iodo-nitro interaction in 2-iodobenzaldehyde 4-nitrophenylhydrazone versus disordered and effectively isolated molecules in 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone. Acta Crystallographica Section C, Crystal Structure Communications. 2003;C59:o98-o101. doi: 10.1107/S0108270103001379

Glidewell, C ; Low, J N ; Skakle, J M S et al. / A chain of edge-fused rings generated by the combination of an N-H center dot center dot center dot O hydrogen bond and an iodo-nitro interaction in 2-iodobenzaldehyde 4-nitrophenylhydrazone versus disordered and effectively isolated molecules in 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone. In: Acta Crystallographica Section C, Crystal Structure Communications. 2003 ; Vol. C59. pp. o98-o101.

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abstract = "Molecules of 2-iodobenzaldehyde 4-nitrophenylhydrazone, C13H10IN3O2, are effectively planar and are linked by an N-H...O hydrogen bond [H...O=2.04 Angstrom, N...O=2.905 (6) Angstrom and NDH...O=166degrees] and a two-centre iodo-nitro interaction [I...O=3.361 (4) Angstrom] into a chain of edge-fused R-3(3) (18) rings. There are no direction-specific interactions between adjacent chains. Molecules of 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone, C13H9IN4O4, are disordered over two orientations with occupancies of 0.681 (5) and 0.319 (5). In the major orientation, there are no direction-specific intermolecular interactions, while for the minor form, a single C-H...O hydrogen bond generates centrosymmetric dimers.",

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T1 - A chain of edge-fused rings generated by the combination of an N-H center dot center dot center dot O hydrogen bond and an iodo-nitro interaction in 2-iodobenzaldehyde 4-nitrophenylhydrazone versus disordered and effectively isolated molecules in 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone

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AU - Wardell, J L

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N2 - Molecules of 2-iodobenzaldehyde 4-nitrophenylhydrazone, C13H10IN3O2, are effectively planar and are linked by an N-H...O hydrogen bond [H...O=2.04 Angstrom, N...O=2.905 (6) Angstrom and NDH...O=166degrees] and a two-centre iodo-nitro interaction [I...O=3.361 (4) Angstrom] into a chain of edge-fused R-3(3) (18) rings. There are no direction-specific interactions between adjacent chains. Molecules of 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone, C13H9IN4O4, are disordered over two orientations with occupancies of 0.681 (5) and 0.319 (5). In the major orientation, there are no direction-specific intermolecular interactions, while for the minor form, a single C-H...O hydrogen bond generates centrosymmetric dimers.

AB - Molecules of 2-iodobenzaldehyde 4-nitrophenylhydrazone, C13H10IN3O2, are effectively planar and are linked by an N-H...O hydrogen bond [H...O=2.04 Angstrom, N...O=2.905 (6) Angstrom and NDH...O=166degrees] and a two-centre iodo-nitro interaction [I...O=3.361 (4) Angstrom] into a chain of edge-fused R-3(3) (18) rings. There are no direction-specific interactions between adjacent chains. Molecules of 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone, C13H9IN4O4, are disordered over two orientations with occupancies of 0.681 (5) and 0.319 (5). In the major orientation, there are no direction-specific intermolecular interactions, while for the minor form, a single C-H...O hydrogen bond generates centrosymmetric dimers.

KW - pi-stacking interactions

KW - interlay

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DO - 10.1107/S0108270103001379

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VL - C59

SP - o98-o101

JO - Acta Crystallographica Section C, Crystal Structure Communications

JF - Acta Crystallographica Section C, Crystal Structure Communications

SN - 0108-2701

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