Crystal structures of the benzene and ethanol solvates of neotame

Zedong Dong; Victor G. Young; Eric J. Munson; Steve A. Schroeder; Indra Prakash; David J.W. Grant

doi:10.1023/A:1026111508373

Crystal structures of the benzene and ethanol solvates of neotame

Zedong Dong, Victor G. Young, Eric J. Munson, Steve A. Schroeder, Indra Prakash, David J.W. Grant

Chemistry (Twin Cities)

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

1 Scopus citations

Abstract

The benzene and ethanol solvates of neotame crystallized from solutions of neotame anhydrate in benzene and ethanol, respectively. The crystal structures of the two solvates were determined by single-crystal X-ray diffraction using synchrotron radiation. The benzene solvate crystallizes in the monoclinic space group, P2₁, Z = 2, with one neotame molecule and one benzene molecule per asymmetric unit. The cell constants are a = 13.060 (6) Å, b = 5.582 (2) Å, c = 17.954 (9) Å, and β = 102.079 (15)°. The ethanol solvate crystallizes in the orthorhombic space group, P2 ₁2₁2₁ with Z = 8 (Z′ = 2). The cell constants are a = 10.047 (4) Å, b = 17.001 (4) Å, and c = 28.948 (7) Å. Intermolecular hydrogen bonding among neotame molecules is evident in the two crystals. The benzene solvate has a nonpolar region containing the benzene molecules, with the benzene rings and alkyl chains of the neotame molecules.

Original language	English (US)
Pages (from-to)	787-793
Number of pages	7
Journal	Journal of Chemical Crystallography
Volume	33
Issue number	10
DOIs	https://doi.org/10.1023/A:1026111508373
State	Published - Oct 2003

Bibliographical note

Funding Information:
We thank The NutraSweet Company for partial financial support and the United States Pharmacopeial Convention for the award of a USP Fellowship in Drug Standards Research to Zedong Dong. We also thank the Supercomputer Institute of the University of Minnesota for supporting our use of the Medicinal Chemistry/Supercomputing Institute Visualization-Workshop Laboratory. In addition, we thank Novartis Corporation for a Graduate Research Fellowship and Pharmacia Corporation for an Enz award, both to Zedong Dong. Use of the ChemMatCARS Sector 15 at the Advanced Photon Source is supported by the National Science Foundation/Department of Energy under grant numbers CHE9522232 and CHE0087817 and by the Illinois Board of Education. Moreover, the Advanced Photon Source is supported by the US Department of Energy, Basic Energy Sciences, Office of Science, under contract no. W-31-109-Eng-38. A special word of thanks goes to David Cookson, Jeff Gebhardt, and Timothy Graber who assisted in these measurements during the commissioning run for the microcrystallography beamline.

Keywords

Benzene solvate
Ethanol solvate
Hydrogen bonding
Hydrophobic region
Neotame
Synchrotron diffraction

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@article{08d76a2ef369401dbc71e982542e9fdd,

title = "Crystal structures of the benzene and ethanol solvates of neotame",

abstract = "The benzene and ethanol solvates of neotame crystallized from solutions of neotame anhydrate in benzene and ethanol, respectively. The crystal structures of the two solvates were determined by single-crystal X-ray diffraction using synchrotron radiation. The benzene solvate crystallizes in the monoclinic space group, P21, Z = 2, with one neotame molecule and one benzene molecule per asymmetric unit. The cell constants are a = 13.060 (6) {\AA}, b = 5.582 (2) {\AA}, c = 17.954 (9) {\AA}, and β = 102.079 (15)°. The ethanol solvate crystallizes in the orthorhombic space group, P2 12121 with Z = 8 (Z′ = 2). The cell constants are a = 10.047 (4) {\AA}, b = 17.001 (4) {\AA}, and c = 28.948 (7) {\AA}. Intermolecular hydrogen bonding among neotame molecules is evident in the two crystals. The benzene solvate has a nonpolar region containing the benzene molecules, with the benzene rings and alkyl chains of the neotame molecules.",

keywords = "Benzene solvate, Ethanol solvate, Hydrogen bonding, Hydrophobic region, Neotame, Synchrotron diffraction",

author = "Zedong Dong and Young, {Victor G.} and Munson, {Eric J.} and Schroeder, {Steve A.} and Indra Prakash and Grant, {David J.W.}",

note = "Funding Information: We thank The NutraSweet Company for partial financial support and the United States Pharmacopeial Convention for the award of a USP Fellowship in Drug Standards Research to Zedong Dong. We also thank the Supercomputer Institute of the University of Minnesota for supporting our use of the Medicinal Chemistry/Supercomputing Institute Visualization-Workshop Laboratory. In addition, we thank Novartis Corporation for a Graduate Research Fellowship and Pharmacia Corporation for an Enz award, both to Zedong Dong. Use of the ChemMatCARS Sector 15 at the Advanced Photon Source is supported by the National Science Foundation/Department of Energy under grant numbers CHE9522232 and CHE0087817 and by the Illinois Board of Education. Moreover, the Advanced Photon Source is supported by the US Department of Energy, Basic Energy Sciences, Office of Science, under contract no. W-31-109-Eng-38. A special word of thanks goes to David Cookson, Jeff Gebhardt, and Timothy Graber who assisted in these measurements during the commissioning run for the microcrystallography beamline.",

year = "2003",

month = oct,

doi = "10.1023/A:1026111508373",

language = "English (US)",

volume = "33",

pages = "787--793",

journal = "Journal of Chemical Crystallography",

issn = "1074-1542",

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TY - JOUR

T1 - Crystal structures of the benzene and ethanol solvates of neotame

AU - Dong, Zedong

AU - Young, Victor G.

AU - Munson, Eric J.

AU - Schroeder, Steve A.

AU - Prakash, Indra

AU - Grant, David J.W.

N1 - Funding Information: We thank The NutraSweet Company for partial financial support and the United States Pharmacopeial Convention for the award of a USP Fellowship in Drug Standards Research to Zedong Dong. We also thank the Supercomputer Institute of the University of Minnesota for supporting our use of the Medicinal Chemistry/Supercomputing Institute Visualization-Workshop Laboratory. In addition, we thank Novartis Corporation for a Graduate Research Fellowship and Pharmacia Corporation for an Enz award, both to Zedong Dong. Use of the ChemMatCARS Sector 15 at the Advanced Photon Source is supported by the National Science Foundation/Department of Energy under grant numbers CHE9522232 and CHE0087817 and by the Illinois Board of Education. Moreover, the Advanced Photon Source is supported by the US Department of Energy, Basic Energy Sciences, Office of Science, under contract no. W-31-109-Eng-38. A special word of thanks goes to David Cookson, Jeff Gebhardt, and Timothy Graber who assisted in these measurements during the commissioning run for the microcrystallography beamline.

PY - 2003/10

Y1 - 2003/10

N2 - The benzene and ethanol solvates of neotame crystallized from solutions of neotame anhydrate in benzene and ethanol, respectively. The crystal structures of the two solvates were determined by single-crystal X-ray diffraction using synchrotron radiation. The benzene solvate crystallizes in the monoclinic space group, P21, Z = 2, with one neotame molecule and one benzene molecule per asymmetric unit. The cell constants are a = 13.060 (6) Å, b = 5.582 (2) Å, c = 17.954 (9) Å, and β = 102.079 (15)°. The ethanol solvate crystallizes in the orthorhombic space group, P2 12121 with Z = 8 (Z′ = 2). The cell constants are a = 10.047 (4) Å, b = 17.001 (4) Å, and c = 28.948 (7) Å. Intermolecular hydrogen bonding among neotame molecules is evident in the two crystals. The benzene solvate has a nonpolar region containing the benzene molecules, with the benzene rings and alkyl chains of the neotame molecules.

AB - The benzene and ethanol solvates of neotame crystallized from solutions of neotame anhydrate in benzene and ethanol, respectively. The crystal structures of the two solvates were determined by single-crystal X-ray diffraction using synchrotron radiation. The benzene solvate crystallizes in the monoclinic space group, P21, Z = 2, with one neotame molecule and one benzene molecule per asymmetric unit. The cell constants are a = 13.060 (6) Å, b = 5.582 (2) Å, c = 17.954 (9) Å, and β = 102.079 (15)°. The ethanol solvate crystallizes in the orthorhombic space group, P2 12121 with Z = 8 (Z′ = 2). The cell constants are a = 10.047 (4) Å, b = 17.001 (4) Å, and c = 28.948 (7) Å. Intermolecular hydrogen bonding among neotame molecules is evident in the two crystals. The benzene solvate has a nonpolar region containing the benzene molecules, with the benzene rings and alkyl chains of the neotame molecules.

KW - Benzene solvate

KW - Ethanol solvate

KW - Hydrogen bonding

KW - Hydrophobic region

KW - Neotame

KW - Synchrotron diffraction

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JO - Journal of Chemical Crystallography

JF - Journal of Chemical Crystallography

SN - 1074-1542

IS - 10

ER -

Crystal structures of the benzene and ethanol solvates of neotame

Abstract

Bibliographical note

Keywords

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