Isomeric nitrophthalimides: sheets built from N-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds

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

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Abstract

Molecules of 3- nitrophthalimide, C8H4N2O4, are linked into sheets by a combination of one N - H ... O hydrogen bond [ H ... O = 1.99 Angstrom, N ... O = 2.8043 ( 14) Angstrom and N - H ... O = 176degrees ] and two independent C - H ... O hydrogen bonds [ H ... O = 2.36 and 2.56 Angstrom, C ... O = 3.1639 ( 16) and 3.4386 ( 16) Angstrom, and C - H ... O = 142 and 153degrees], and these sheets are linked into pairs by a single pi - pi stacking interaction. Molecules of isomeric 4- nitrophthalimide are linked into sheets by a combination of one three- centre N - H ... ( O) (2) hydrogen bond [ H ... O = 2.14 and 2.55 Angstrom, N ... O = 2.974 ( 3) and 3.231 ( 3) Angstrom, N - H ... O = 151 and 131degrees, and O ... H ... O = 76degrees] and two independent two- centre C - H ... O hydrogen bonds [ H ... O = 2.38 and 2.54 Angstrom, C ... O = 3.257 ( 4) and 3.452 ( 4) Angstrom, and C - H ... O = 156 and 168degrees].

Original languageEnglish
Pages (from-to)o872-o875
Number of pages4
JournalActa Crystallographica Section C, Crystal Structure Communications
VolumeC60
DOIs
Publication statusPublished - 2004

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Hydrogen
Hydrogen bonds
Molecules

Keywords

  • absolute-structure
  • crystals

Cite this

@article{8fe1a9c923fc42259bc21fb2a35f4fe8,
title = "Isomeric nitrophthalimides: sheets built from N-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds",
abstract = "Molecules of 3- nitrophthalimide, C8H4N2O4, are linked into sheets by a combination of one N - H ... O hydrogen bond [ H ... O = 1.99 Angstrom, N ... O = 2.8043 ( 14) Angstrom and N - H ... O = 176degrees ] and two independent C - H ... O hydrogen bonds [ H ... O = 2.36 and 2.56 Angstrom, C ... O = 3.1639 ( 16) and 3.4386 ( 16) Angstrom, and C - H ... O = 142 and 153degrees], and these sheets are linked into pairs by a single pi - pi stacking interaction. Molecules of isomeric 4- nitrophthalimide are linked into sheets by a combination of one three- centre N - H ... ( O) (2) hydrogen bond [ H ... O = 2.14 and 2.55 Angstrom, N ... O = 2.974 ( 3) and 3.231 ( 3) Angstrom, N - H ... O = 151 and 131degrees, and O ... H ... O = 76degrees] and two independent two- centre C - H ... O hydrogen bonds [ H ... O = 2.38 and 2.54 Angstrom, C ... O = 3.257 ( 4) and 3.452 ( 4) Angstrom, and C - H ... O = 156 and 168degrees].",
keywords = "absolute-structure, crystals",
author = "C Glidewell and Low, {J N} and Skakle, {J M S} and Wardell, {J L}",
year = "2004",
doi = "10.1107/S0108270104026137",
language = "English",
volume = "C60",
pages = "o872--o875",
journal = "Acta Crystallographica Section C, Crystal Structure Communications",
issn = "0108-2701",
publisher = "Wiley-Blackwell",

}

TY - JOUR

T1 - Isomeric nitrophthalimides: sheets built from N-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds

AU - Glidewell, C

AU - Low, J N

AU - Skakle, J M S

AU - Wardell, J L

PY - 2004

Y1 - 2004

N2 - Molecules of 3- nitrophthalimide, C8H4N2O4, are linked into sheets by a combination of one N - H ... O hydrogen bond [ H ... O = 1.99 Angstrom, N ... O = 2.8043 ( 14) Angstrom and N - H ... O = 176degrees ] and two independent C - H ... O hydrogen bonds [ H ... O = 2.36 and 2.56 Angstrom, C ... O = 3.1639 ( 16) and 3.4386 ( 16) Angstrom, and C - H ... O = 142 and 153degrees], and these sheets are linked into pairs by a single pi - pi stacking interaction. Molecules of isomeric 4- nitrophthalimide are linked into sheets by a combination of one three- centre N - H ... ( O) (2) hydrogen bond [ H ... O = 2.14 and 2.55 Angstrom, N ... O = 2.974 ( 3) and 3.231 ( 3) Angstrom, N - H ... O = 151 and 131degrees, and O ... H ... O = 76degrees] and two independent two- centre C - H ... O hydrogen bonds [ H ... O = 2.38 and 2.54 Angstrom, C ... O = 3.257 ( 4) and 3.452 ( 4) Angstrom, and C - H ... O = 156 and 168degrees].

AB - Molecules of 3- nitrophthalimide, C8H4N2O4, are linked into sheets by a combination of one N - H ... O hydrogen bond [ H ... O = 1.99 Angstrom, N ... O = 2.8043 ( 14) Angstrom and N - H ... O = 176degrees ] and two independent C - H ... O hydrogen bonds [ H ... O = 2.36 and 2.56 Angstrom, C ... O = 3.1639 ( 16) and 3.4386 ( 16) Angstrom, and C - H ... O = 142 and 153degrees], and these sheets are linked into pairs by a single pi - pi stacking interaction. Molecules of isomeric 4- nitrophthalimide are linked into sheets by a combination of one three- centre N - H ... ( O) (2) hydrogen bond [ H ... O = 2.14 and 2.55 Angstrom, N ... O = 2.974 ( 3) and 3.231 ( 3) Angstrom, N - H ... O = 151 and 131degrees, and O ... H ... O = 76degrees] and two independent two- centre C - H ... O hydrogen bonds [ H ... O = 2.38 and 2.54 Angstrom, C ... O = 3.257 ( 4) and 3.452 ( 4) Angstrom, and C - H ... O = 156 and 168degrees].

KW - absolute-structure

KW - crystals

U2 - 10.1107/S0108270104026137

DO - 10.1107/S0108270104026137

M3 - Article

VL - C60

SP - o872-o875

JO - Acta Crystallographica Section C, Crystal Structure Communications

JF - Acta Crystallographica Section C, Crystal Structure Communications

SN - 0108-2701

ER -