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Co-crystallization of 3,5-dinitrobenzoic acid with two antipsychotic agents: a simple 1:1 salt with trihexyphenidyl and a 1:2 acid salt containing a very short O-H···O hydrogen bond with chlorprothixene

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Co-crystallization of 3,5-dinitrobenzoic acid with two antipsychotic agents : a simple 1:1 salt with trihexyphenidyl and a 1:2 acid salt containing a very short O-H···O hydrogen bond with chlorprothixene. / Shaibah, Mohammed A. E.; Yathirajan, Hemmige S.; Rathore, Ravindranath S.; Furuya, Tetsundo; Haraguchi, Tomoyuki; Akitsu, Takashiro; Glidewell, Christopher.

In: Acta Crystallographica Section E, Vol. 75, No. 2, 01.02.2019, p. 292-298.

Research output: Contribution to journalArticlepeer-review

Harvard

Shaibah, MAE, Yathirajan, HS, Rathore, RS, Furuya, T, Haraguchi, T, Akitsu, T & Glidewell, C 2019, 'Co-crystallization of 3,5-dinitrobenzoic acid with two antipsychotic agents: a simple 1:1 salt with trihexyphenidyl and a 1:2 acid salt containing a very short O-H···O hydrogen bond with chlorprothixene', Acta Crystallographica Section E, vol. 75, no. 2, pp. 292-298. https://doi.org/10.1107/S2056989019001385

APA

Shaibah, M. A. E., Yathirajan, H. S., Rathore, R. S., Furuya, T., Haraguchi, T., Akitsu, T., & Glidewell, C. (2019). Co-crystallization of 3,5-dinitrobenzoic acid with two antipsychotic agents: a simple 1:1 salt with trihexyphenidyl and a 1:2 acid salt containing a very short O-H···O hydrogen bond with chlorprothixene. Acta Crystallographica Section E, 75(2), 292-298. https://doi.org/10.1107/S2056989019001385

Vancouver

Shaibah MAE, Yathirajan HS, Rathore RS, Furuya T, Haraguchi T, Akitsu T et al. Co-crystallization of 3,5-dinitrobenzoic acid with two antipsychotic agents: a simple 1:1 salt with trihexyphenidyl and a 1:2 acid salt containing a very short O-H···O hydrogen bond with chlorprothixene. Acta Crystallographica Section E. 2019 Feb 1;75(2):292-298. https://doi.org/10.1107/S2056989019001385

Author

Shaibah, Mohammed A. E. ; Yathirajan, Hemmige S. ; Rathore, Ravindranath S. ; Furuya, Tetsundo ; Haraguchi, Tomoyuki ; Akitsu, Takashiro ; Glidewell, Christopher. / Co-crystallization of 3,5-dinitrobenzoic acid with two antipsychotic agents : a simple 1:1 salt with trihexyphenidyl and a 1:2 acid salt containing a very short O-H···O hydrogen bond with chlorprothixene. In: Acta Crystallographica Section E. 2019 ; Vol. 75, No. 2. pp. 292-298.

Bibtex - Download

@article{3227cb2a04e7414fb8a2b381ddfebac5,
title = "Co-crystallization of 3,5-dinitrobenzoic acid with two antipsychotic agents: a simple 1:1 salt with trihexyphenidyl and a 1:2 acid salt containing a very short O-H···O hydrogen bond with chlorprothixene",
abstract = "Co-crystallization of racemic 1-cyclo­hexyl-1-phenyl-3-(piperidin-1-yl)propan-1-ol (trihexyphenid­yl) with 3,5-di­nitro­benzoic acid gives a simple 1:1 salt, namely 1-(3-cyclo­hexyl-3-hy­droxy-3-phenyl­prop­yl)piperidin-1-ium 3,5-di­nitro­benzoate, C20H 32NO +·C 7H 3N 2O 6 −, (I), whereas a similar co-crystallization using (Z)-3-(2-chloro-9 H-thioxanthen-9-yl)- N, N-di­methyl­propan-1-amine (chlorprothixene) gives a 1:2 acid salt, namely (Z)-3-(2-chloro-9 H-thioxanthen-9-yl)- N, N-di­methyl­propan-1-aminium hydrogen bis­(3,5-di­nitro­benzoate), C18H 19ClNS +·[H(C 7H 3N 2O 6) 2] −, (II), the anion of which contains a very short O—H⋯O hydrogen bond, with dimensions O—H = 1.04 (3) {\AA}, H⋯O = 1.41 (3) {\AA}, O⋯O = 2.4197 (15) {\AA} and O—H⋯O = 161 (3)°. In the cation of (I), the cyclo­hexyl and piperidyl rings both adopt chair conformations, whereas in the cation of (II), the central heterocyclic ring adopts a boat conformation, so that the dihedral angle between the two aryl rings is 41.56 (4)°. A combination of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds links the ions of (I) into a complex chain of rings, and these chains are linked into sheets by π– π stacking inter­actions between inversion-related pairs of anions. In compound (II), a different combination of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds links the ions into sheets. Comparisons are made with some related structures.",
keywords = "Co-crystallization, Acid salts, Crystal structure, Molecular conformation, Hydrogen bonding, Supramolecular assembly",
author = "Shaibah, {Mohammed A. E.} and Yathirajan, {Hemmige S.} and Rathore, {Ravindranath S.} and Tetsundo Furuya and Tomoyuki Haraguchi and Takashiro Akitsu and Christopher Glidewell",
note = "HSY is grateful to the UGC, New Delhi, for the award of a BSR Faculty Fellowship for three years.",
year = "2019",
month = feb,
day = "1",
doi = "10.1107/S2056989019001385",
language = "English",
volume = "75",
pages = "292--298",
journal = "Acta Crystallographica Section E Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",
number = "2",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Co-crystallization of 3,5-dinitrobenzoic acid with two antipsychotic agents

T2 - a simple 1:1 salt with trihexyphenidyl and a 1:2 acid salt containing a very short O-H···O hydrogen bond with chlorprothixene

AU - Shaibah, Mohammed A. E.

AU - Yathirajan, Hemmige S.

AU - Rathore, Ravindranath S.

AU - Furuya, Tetsundo

AU - Haraguchi, Tomoyuki

AU - Akitsu, Takashiro

AU - Glidewell, Christopher

N1 - HSY is grateful to the UGC, New Delhi, for the award of a BSR Faculty Fellowship for three years.

PY - 2019/2/1

Y1 - 2019/2/1

N2 - Co-crystallization of racemic 1-cyclo­hexyl-1-phenyl-3-(piperidin-1-yl)propan-1-ol (trihexyphenid­yl) with 3,5-di­nitro­benzoic acid gives a simple 1:1 salt, namely 1-(3-cyclo­hexyl-3-hy­droxy-3-phenyl­prop­yl)piperidin-1-ium 3,5-di­nitro­benzoate, C20H 32NO +·C 7H 3N 2O 6 −, (I), whereas a similar co-crystallization using (Z)-3-(2-chloro-9 H-thioxanthen-9-yl)- N, N-di­methyl­propan-1-amine (chlorprothixene) gives a 1:2 acid salt, namely (Z)-3-(2-chloro-9 H-thioxanthen-9-yl)- N, N-di­methyl­propan-1-aminium hydrogen bis­(3,5-di­nitro­benzoate), C18H 19ClNS +·[H(C 7H 3N 2O 6) 2] −, (II), the anion of which contains a very short O—H⋯O hydrogen bond, with dimensions O—H = 1.04 (3) Å, H⋯O = 1.41 (3) Å, O⋯O = 2.4197 (15) Å and O—H⋯O = 161 (3)°. In the cation of (I), the cyclo­hexyl and piperidyl rings both adopt chair conformations, whereas in the cation of (II), the central heterocyclic ring adopts a boat conformation, so that the dihedral angle between the two aryl rings is 41.56 (4)°. A combination of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds links the ions of (I) into a complex chain of rings, and these chains are linked into sheets by π– π stacking inter­actions between inversion-related pairs of anions. In compound (II), a different combination of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds links the ions into sheets. Comparisons are made with some related structures.

AB - Co-crystallization of racemic 1-cyclo­hexyl-1-phenyl-3-(piperidin-1-yl)propan-1-ol (trihexyphenid­yl) with 3,5-di­nitro­benzoic acid gives a simple 1:1 salt, namely 1-(3-cyclo­hexyl-3-hy­droxy-3-phenyl­prop­yl)piperidin-1-ium 3,5-di­nitro­benzoate, C20H 32NO +·C 7H 3N 2O 6 −, (I), whereas a similar co-crystallization using (Z)-3-(2-chloro-9 H-thioxanthen-9-yl)- N, N-di­methyl­propan-1-amine (chlorprothixene) gives a 1:2 acid salt, namely (Z)-3-(2-chloro-9 H-thioxanthen-9-yl)- N, N-di­methyl­propan-1-aminium hydrogen bis­(3,5-di­nitro­benzoate), C18H 19ClNS +·[H(C 7H 3N 2O 6) 2] −, (II), the anion of which contains a very short O—H⋯O hydrogen bond, with dimensions O—H = 1.04 (3) Å, H⋯O = 1.41 (3) Å, O⋯O = 2.4197 (15) Å and O—H⋯O = 161 (3)°. In the cation of (I), the cyclo­hexyl and piperidyl rings both adopt chair conformations, whereas in the cation of (II), the central heterocyclic ring adopts a boat conformation, so that the dihedral angle between the two aryl rings is 41.56 (4)°. A combination of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds links the ions of (I) into a complex chain of rings, and these chains are linked into sheets by π– π stacking inter­actions between inversion-related pairs of anions. In compound (II), a different combination of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds links the ions into sheets. Comparisons are made with some related structures.

KW - Co-crystallization

KW - Acid salts

KW - Crystal structure

KW - Molecular conformation

KW - Hydrogen bonding

KW - Supramolecular assembly

U2 - 10.1107/S2056989019001385

DO - 10.1107/S2056989019001385

M3 - Article

VL - 75

SP - 292

EP - 298

JO - Acta Crystallographica Section E Crystallographic Communications

JF - Acta Crystallographica Section E Crystallographic Communications

SN - 2056-9890

IS - 2

ER -

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