Three N-2-benzoyloxybenzamidines: sheet structures built from hard and soft hydrogen bonds and aromatic pi-pi stacking interactions

C E M Carvalho, S M S V Wardell, J L Wardell, J M S Skakle, J N Low, C Glidewell

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Abstract

Molecules of the title compounds N-2-( benzoyloxy) benzamidine, C14H12N2O2, ( I), N-2-( 2- hydroxybenzoyloxy) benzamidine, C14H12N2O3, ( II), and N-2- benzoyloxy- 2- hydroxybenzamidine, C14H12N2O3, ( III), all have extended chain conformations, with the aryl groups remote from one another. In ( I), the molecules are linked into chains by a single N - H ... N hydrogen bond [H ... N = 2.15 Angstrom, N ... N = 3.029 (2) Angstrom and N - H ... N = 153degrees] and these chains are linked into sheets by means of aromatic pi - pi stacking interactions. There is one intramolecular O - H ... O hydrogen bond in ( II), and a combination of one three-centre N - H ...( N, O) hydrogen bond [H ... N = 2.46 Angstrom, H ... O = 2.31 Angstrom, N ... N = 3.190 ( 2) Angstrom, N ... O = 3.146 ( 2) Angstrom, N - H ... N = 138degrees and N - H ... O = 154degrees] and one two- centre C - H ... O hydrogen bond [H ... O = 2.46 Angstrom, C ... O = 3.405 (2) Angstrom and C - H ... O = 173degrees] links the molecules into sheets. In ( III), an intramolecular O H H ... N hydrogen bond and two N - H ... O hydrogen bonds [H ... O = 2.26 and 2.10 Angstrom, N ... O = 2.975 ( 2) and 2.954 ( 2) Angstrom, and N - H ... O = 138 and 163degrees] link the molecules into sheets.

Original languageEnglish
Number of pages5
JournalActa Crystallographica Section C, Crystal Structure Communications
Volume60
DOIs
Publication statusPublished - 2004

Cite this

Three N-2-benzoyloxybenzamidines: sheet structures built from hard and soft hydrogen bonds and aromatic pi-pi stacking interactions. / Carvalho, C E M ; Wardell, S M S V ; Wardell, J L ; Skakle, J M S ; Low, J N ; Glidewell, C .

In: Acta Crystallographica Section C, Crystal Structure Communications, Vol. 60, 2004.

Research output: Contribution to journalArticle

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title = "Three N-2-benzoyloxybenzamidines: sheet structures built from hard and soft hydrogen bonds and aromatic pi-pi stacking interactions",
abstract = "Molecules of the title compounds N-2-( benzoyloxy) benzamidine, C14H12N2O2, ( I), N-2-( 2- hydroxybenzoyloxy) benzamidine, C14H12N2O3, ( II), and N-2- benzoyloxy- 2- hydroxybenzamidine, C14H12N2O3, ( III), all have extended chain conformations, with the aryl groups remote from one another. In ( I), the molecules are linked into chains by a single N - H ... N hydrogen bond [H ... N = 2.15 Angstrom, N ... N = 3.029 (2) Angstrom and N - H ... N = 153degrees] and these chains are linked into sheets by means of aromatic pi - pi stacking interactions. There is one intramolecular O - H ... O hydrogen bond in ( II), and a combination of one three-centre N - H ...( N, O) hydrogen bond [H ... N = 2.46 Angstrom, H ... O = 2.31 Angstrom, N ... N = 3.190 ( 2) Angstrom, N ... O = 3.146 ( 2) Angstrom, N - H ... N = 138degrees and N - H ... O = 154degrees] and one two- centre C - H ... O hydrogen bond [H ... O = 2.46 Angstrom, C ... O = 3.405 (2) Angstrom and C - H ... O = 173degrees] links the molecules into sheets. In ( III), an intramolecular O H H ... N hydrogen bond and two N - H ... O hydrogen bonds [H ... O = 2.26 and 2.10 Angstrom, N ... O = 2.975 ( 2) and 2.954 ( 2) Angstrom, and N - H ... O = 138 and 163degrees] link the molecules into sheets.",
author = "Carvalho, {C E M} and Wardell, {S M S V} and Wardell, {J L} and Skakle, {J M S} and Low, {J N} and C Glidewell",
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T1 - Three N-2-benzoyloxybenzamidines: sheet structures built from hard and soft hydrogen bonds and aromatic pi-pi stacking interactions

AU - Carvalho, C E M

AU - Wardell, S M S V

AU - Wardell, J L

AU - Skakle, J M S

AU - Low, J N

AU - Glidewell, C

PY - 2004

Y1 - 2004

N2 - Molecules of the title compounds N-2-( benzoyloxy) benzamidine, C14H12N2O2, ( I), N-2-( 2- hydroxybenzoyloxy) benzamidine, C14H12N2O3, ( II), and N-2- benzoyloxy- 2- hydroxybenzamidine, C14H12N2O3, ( III), all have extended chain conformations, with the aryl groups remote from one another. In ( I), the molecules are linked into chains by a single N - H ... N hydrogen bond [H ... N = 2.15 Angstrom, N ... N = 3.029 (2) Angstrom and N - H ... N = 153degrees] and these chains are linked into sheets by means of aromatic pi - pi stacking interactions. There is one intramolecular O - H ... O hydrogen bond in ( II), and a combination of one three-centre N - H ...( N, O) hydrogen bond [H ... N = 2.46 Angstrom, H ... O = 2.31 Angstrom, N ... N = 3.190 ( 2) Angstrom, N ... O = 3.146 ( 2) Angstrom, N - H ... N = 138degrees and N - H ... O = 154degrees] and one two- centre C - H ... O hydrogen bond [H ... O = 2.46 Angstrom, C ... O = 3.405 (2) Angstrom and C - H ... O = 173degrees] links the molecules into sheets. In ( III), an intramolecular O H H ... N hydrogen bond and two N - H ... O hydrogen bonds [H ... O = 2.26 and 2.10 Angstrom, N ... O = 2.975 ( 2) and 2.954 ( 2) Angstrom, and N - H ... O = 138 and 163degrees] link the molecules into sheets.

AB - Molecules of the title compounds N-2-( benzoyloxy) benzamidine, C14H12N2O2, ( I), N-2-( 2- hydroxybenzoyloxy) benzamidine, C14H12N2O3, ( II), and N-2- benzoyloxy- 2- hydroxybenzamidine, C14H12N2O3, ( III), all have extended chain conformations, with the aryl groups remote from one another. In ( I), the molecules are linked into chains by a single N - H ... N hydrogen bond [H ... N = 2.15 Angstrom, N ... N = 3.029 (2) Angstrom and N - H ... N = 153degrees] and these chains are linked into sheets by means of aromatic pi - pi stacking interactions. There is one intramolecular O - H ... O hydrogen bond in ( II), and a combination of one three-centre N - H ...( N, O) hydrogen bond [H ... N = 2.46 Angstrom, H ... O = 2.31 Angstrom, N ... N = 3.190 ( 2) Angstrom, N ... O = 3.146 ( 2) Angstrom, N - H ... N = 138degrees and N - H ... O = 154degrees] and one two- centre C - H ... O hydrogen bond [H ... O = 2.46 Angstrom, C ... O = 3.405 (2) Angstrom and C - H ... O = 173degrees] links the molecules into sheets. In ( III), an intramolecular O H H ... N hydrogen bond and two N - H ... O hydrogen bonds [H ... O = 2.26 and 2.10 Angstrom, N ... O = 2.975 ( 2) and 2.954 ( 2) Angstrom, and N - H ... O = 138 and 163degrees] link the molecules into sheets.

U2 - 10.1107/S0108270103025435

DO - 10.1107/S0108270103025435

M3 - Article

VL - 60

JO - Acta Crystallographica Section C, Crystal Structure Communications

JF - Acta Crystallographica Section C, Crystal Structure Communications

SN - 0108-2701

ER -