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

doi:10.1107/S0108270104026137

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

School of Chemistry

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

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 language	English
Number of pages	4
Journal	Acta Crystallographica Section C-Crystal Structure Communications
Volume	60
DOIs	https://doi.org/10.1107/S0108270104026137
Publication status	Published - Dec 2004

Keywords

ABSOLUTE-STRUCTURE
CRYSTALS

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@article{2ff3e1a855824479a5b1c064039ca373,

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",

month = dec,

doi = "10.1107/S0108270104026137",

language = "English",

volume = "60",

journal = "Acta Crystallographica Section C-Crystal Structure Communications",

issn = "1600-5759",

publisher = "International Union of Crystallography",

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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 - 2004/12

Y1 - 2004/12

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

SN - 1600-5759

VL - 60

JO - Acta Crystallographica Section C-Crystal Structure Communications

JF - Acta Crystallographica Section C-Crystal Structure Communications

ER -

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

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