Structures of cefradine dihydrate and cefaclor dihydrate from DFT-D calculations

Research output: Contribution to journalJournal articleResearchpeer-review

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Structures of cefradine dihydrate and cefaclor dihydrate from DFT-D calculations. / van de Streek, Jacco; Rantanen, Jukka; Bond, Andrew D.

In: Acta Crystallographica. Section C: Crystal Structure Communications, Vol. 69, No. Pt 11, 11.2013, p. 1229-33.

Research output: Contribution to journalJournal articleResearchpeer-review

Harvard

van de Streek, J, Rantanen, J & Bond, AD 2013, 'Structures of cefradine dihydrate and cefaclor dihydrate from DFT-D calculations', Acta Crystallographica. Section C: Crystal Structure Communications, vol. 69, no. Pt 11, pp. 1229-33. https://doi.org/10.1107/S0108270113026863

APA

van de Streek, J., Rantanen, J., & Bond, A. D. (2013). Structures of cefradine dihydrate and cefaclor dihydrate from DFT-D calculations. Acta Crystallographica. Section C: Crystal Structure Communications, 69(Pt 11), 1229-33. https://doi.org/10.1107/S0108270113026863

Vancouver

van de Streek J, Rantanen J, Bond AD. Structures of cefradine dihydrate and cefaclor dihydrate from DFT-D calculations. Acta Crystallographica. Section C: Crystal Structure Communications. 2013 Nov;69(Pt 11):1229-33. https://doi.org/10.1107/S0108270113026863

Author

van de Streek, Jacco ; Rantanen, Jukka ; Bond, Andrew D. / Structures of cefradine dihydrate and cefaclor dihydrate from DFT-D calculations. In: Acta Crystallographica. Section C: Crystal Structure Communications. 2013 ; Vol. 69, No. Pt 11. pp. 1229-33.

Bibtex

@article{57747e786a954bcab1563266cbfeea9b,
title = "Structures of cefradine dihydrate and cefaclor dihydrate from DFT-D calculations",
abstract = "The crystal structure of cefradine dihydrate, C16H19N3O4S·2H2O, is considered in the pharmaceutical sciences to be the epitome of an isolated-site hydrate. The structure from single-crystal X-ray data was described in 1976, but atomic coordinates were not published. The atomic coordinates are determined here by combining the information available from the published single-crystal data with a dispersion-corrected density functional theory (DFT-D) method that has been validated to reproduce molecular crystal structures very accurately. Additional proof for the correctness of the structure comes from comparison with cefaclor dihydrate, C15H14ClN3O4S·2H2O, which is isomorphous and for which more complete single-crystal data are available. H-atom positions have not previously been published for either compound. The DFT-D calculations confirm that both cefradine and cefaclor are present in the zwitterionic form in the two dihydrate structures. A potential ambiguity concerning the orientation of the cyclohexadienyl ring in cefradine dihydrate is also clarified, and on the basis of the calculated energies it is shown that disorder should not be expected at room temperature. The DFT-D methods can be applied to recover full structural data in cases where only partial information is available, and where it may not be possible or desirable to obtain new experimental data.",
keywords = "Cefaclor, Cephradine, Crystallography, X-Ray, Cyclohexenes, Hydrogen Bonding, Quantum Theory",
author = "{van de Streek}, Jacco and Jukka Rantanen and Bond, {Andrew D}",
year = "2013",
month = "11",
doi = "10.1107/S0108270113026863",
language = "English",
volume = "69",
pages = "1229--33",
journal = "Acta crystallographica. Section C, Structural chemistry",
issn = "2053-2296",
publisher = "Wiley",
number = "Pt 11",

}

RIS

TY - JOUR

T1 - Structures of cefradine dihydrate and cefaclor dihydrate from DFT-D calculations

AU - van de Streek, Jacco

AU - Rantanen, Jukka

AU - Bond, Andrew D

PY - 2013/11

Y1 - 2013/11

N2 - The crystal structure of cefradine dihydrate, C16H19N3O4S·2H2O, is considered in the pharmaceutical sciences to be the epitome of an isolated-site hydrate. The structure from single-crystal X-ray data was described in 1976, but atomic coordinates were not published. The atomic coordinates are determined here by combining the information available from the published single-crystal data with a dispersion-corrected density functional theory (DFT-D) method that has been validated to reproduce molecular crystal structures very accurately. Additional proof for the correctness of the structure comes from comparison with cefaclor dihydrate, C15H14ClN3O4S·2H2O, which is isomorphous and for which more complete single-crystal data are available. H-atom positions have not previously been published for either compound. The DFT-D calculations confirm that both cefradine and cefaclor are present in the zwitterionic form in the two dihydrate structures. A potential ambiguity concerning the orientation of the cyclohexadienyl ring in cefradine dihydrate is also clarified, and on the basis of the calculated energies it is shown that disorder should not be expected at room temperature. The DFT-D methods can be applied to recover full structural data in cases where only partial information is available, and where it may not be possible or desirable to obtain new experimental data.

AB - The crystal structure of cefradine dihydrate, C16H19N3O4S·2H2O, is considered in the pharmaceutical sciences to be the epitome of an isolated-site hydrate. The structure from single-crystal X-ray data was described in 1976, but atomic coordinates were not published. The atomic coordinates are determined here by combining the information available from the published single-crystal data with a dispersion-corrected density functional theory (DFT-D) method that has been validated to reproduce molecular crystal structures very accurately. Additional proof for the correctness of the structure comes from comparison with cefaclor dihydrate, C15H14ClN3O4S·2H2O, which is isomorphous and for which more complete single-crystal data are available. H-atom positions have not previously been published for either compound. The DFT-D calculations confirm that both cefradine and cefaclor are present in the zwitterionic form in the two dihydrate structures. A potential ambiguity concerning the orientation of the cyclohexadienyl ring in cefradine dihydrate is also clarified, and on the basis of the calculated energies it is shown that disorder should not be expected at room temperature. The DFT-D methods can be applied to recover full structural data in cases where only partial information is available, and where it may not be possible or desirable to obtain new experimental data.

KW - Cefaclor

KW - Cephradine

KW - Crystallography, X-Ray

KW - Cyclohexenes

KW - Hydrogen Bonding

KW - Quantum Theory

U2 - 10.1107/S0108270113026863

DO - 10.1107/S0108270113026863

M3 - Journal article

VL - 69

SP - 1229

EP - 1233

JO - Acta crystallographica. Section C, Structural chemistry

JF - Acta crystallographica. Section C, Structural chemistry

SN - 2053-2296

IS - Pt 11

ER -

ID: 120401919