The crystal structures of two chalcones: (2E)-1-(5-chlorothiophen-2-yl)-3-(2-methylphenyl)prop-2-en-1-one and (2E)-1-(anthracen-9-yl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one

Marisiddaiah Girisha; Hemmige S. Yathirajan; Jerry P. Jasinski; Christopher Glidewell

doi:10.1107/S2056989016011592

The crystal structures of two chalcones: (2E)-1-(5-chlorothiophen-2-yl)-3-(2-methylphenyl)prop-2-en-1-one and (2E)-1-(anthracen-9-yl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one

Marisiddaiah Girisha, Hemmige S. Yathirajan, Jerry P. Jasinski, Christopher Glidewell

School of Chemistry

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Abstract

In the crystal of compound (I), C₁₄H₁₁ClOS, molecules are linked by C---H···O hydrogen bonds to form simple it C(5) chains. Compound (II), C₂₆H₂₂O, crystallizes with it Z' = 2 in space group it P-1; one of the molecules is fully ordered but the other is disordered over two sets of atomic sites having occupancies 0.644 (3) and 0.356 (3). The two disordered components differ from one another in the orientation of the isopropyl substituents, and both differ from the ordered molecules in the arrangement of the central propenone spacer unit, so that the crystal of (II) contains three distinct conformers. The ordered and disordered conformers each form a it C(8) chain built from a single type of C---H···O hydrogen bond but those formed by the disordered conformers differ from that formed by the ordered form.

Original language	English
Pages (from-to)	1153-1158
Number of pages	6
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	72
Issue number	8
DOIs	https://doi.org/10.1107/S2056989016011592
Publication status	Published - 1 Aug 2016

Keywords

Crystal structure
Synthesis
Chalcones
Molecular structure
Molecular conformation
Conformational disorder
Hydrogen bonding
Supramolecular assembly

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Glidewell_2016_ACSE_TwoChalcones_CC
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Data underpinning - The crystal structures of two chalcones: (2E)-1-(5-chlorothiophen-2-yl)-3-(2-methylphenyl)prop-2-en-1-one and (2E)-1-(anthracen-9-yl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one
Girisha, M. G. (Creator), Yathirajan, H. S. (Creator), Jasinski, J. P. (Creator) & Glidewell, C. (Creator), Cambridge Crystallographic Data Centre, 2016
https://dx.doi.org/10.5517/ccdc.csd.cc1m4ndt and one more link, https://dx.doi.org/10.5517/ccdc.csd.cc1m4nfv (show fewer)
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Girisha, M., Yathirajan, H. S., Jasinski, J. P., & Glidewell, C. (2016). The crystal structures of two chalcones: (2E)-1-(5-chlorothiophen-2-yl)-3-(2-methylphenyl)prop-2-en-1-one and (2E)-1-(anthracen-9-yl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one. Acta Crystallographica Section E: Crystallographic Communications , 72(8), 1153-1158. https://doi.org/10.1107/S2056989016011592

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title = "The crystal structures of two chalcones: (2E)-1-(5-chlorothiophen-2-yl)-3-(2-methylphenyl)prop-2-en-1-one and (2E)-1-(anthracen-9-yl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one",

abstract = "In the crystal of compound (I), C14H11ClOS, molecules are linked by C---H···O hydrogen bonds to form simple it C(5) chains. Compound (II), C26H22O, crystallizes with it Z' = 2 in space group it P-1; one of the molecules is fully ordered but the other is disordered over two sets of atomic sites having occupancies 0.644 (3) and 0.356 (3). The two disordered components differ from one another in the orientation of the isopropyl substituents, and both differ from the ordered molecules in the arrangement of the central propenone spacer unit, so that the crystal of (II) contains three distinct conformers. The ordered and disordered conformers each form a it C(8) chain built from a single type of C---H···O hydrogen bond but those formed by the disordered conformers differ from that formed by the ordered form.",

keywords = "Crystal structure, Synthesis, Chalcones, Molecular structure, Molecular conformation, Conformational disorder, Hydrogen bonding, Supramolecular assembly",

author = "Marisiddaiah Girisha and Yathirajan, {Hemmige S.} and Jasinski, {Jerry P.} and Christopher Glidewell",

note = "MG thanks the UGC for the award of a Rajeev Gandhi fellowship and HSY thanks the University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (grant No. 1039027) for funds to purchase the X-ray diffractometer.",

year = "2016",

month = aug,

day = "1",

doi = "10.1107/S2056989016011592",

language = "English",

volume = "72",

pages = "1153--1158",

journal = "Acta Crystallographica Section E: Crystallographic Communications ",

issn = "2056-9890",

publisher = "International Union of Crystallography",

number = "8",

}

Girisha, M, Yathirajan, HS, Jasinski, JP & Glidewell, C 2016, 'The crystal structures of two chalcones: (2E)-1-(5-chlorothiophen-2-yl)-3-(2-methylphenyl)prop-2-en-1-one and (2E)-1-(anthracen-9-yl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one', Acta Crystallographica Section E: Crystallographic Communications , vol. 72, no. 8, pp. 1153-1158. https://doi.org/10.1107/S2056989016011592

The crystal structures of two chalcones: (2E)-1-(5-chlorothiophen-2-yl)-3-(2-methylphenyl)prop-2-en-1-one and (2E)-1-(anthracen-9-yl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one. / Girisha, Marisiddaiah; Yathirajan, Hemmige S.; Jasinski, Jerry P. et al.
In: Acta Crystallographica Section E: Crystallographic Communications , Vol. 72, No. 8, 01.08.2016, p. 1153-1158.

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

TY - JOUR

T1 - The crystal structures of two chalcones: (2E)-1-(5-chlorothiophen-2-yl)-3-(2-methylphenyl)prop-2-en-1-one and (2E)-1-(anthracen-9-yl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one

AU - Girisha, Marisiddaiah

AU - Yathirajan, Hemmige S.

AU - Jasinski, Jerry P.

AU - Glidewell, Christopher

N1 - MG thanks the UGC for the award of a Rajeev Gandhi fellowship and HSY thanks the University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (grant No. 1039027) for funds to purchase the X-ray diffractometer.

PY - 2016/8/1

Y1 - 2016/8/1

N2 - In the crystal of compound (I), C14H11ClOS, molecules are linked by C---H···O hydrogen bonds to form simple it C(5) chains. Compound (II), C26H22O, crystallizes with it Z' = 2 in space group it P-1; one of the molecules is fully ordered but the other is disordered over two sets of atomic sites having occupancies 0.644 (3) and 0.356 (3). The two disordered components differ from one another in the orientation of the isopropyl substituents, and both differ from the ordered molecules in the arrangement of the central propenone spacer unit, so that the crystal of (II) contains three distinct conformers. The ordered and disordered conformers each form a it C(8) chain built from a single type of C---H···O hydrogen bond but those formed by the disordered conformers differ from that formed by the ordered form.

AB - In the crystal of compound (I), C14H11ClOS, molecules are linked by C---H···O hydrogen bonds to form simple it C(5) chains. Compound (II), C26H22O, crystallizes with it Z' = 2 in space group it P-1; one of the molecules is fully ordered but the other is disordered over two sets of atomic sites having occupancies 0.644 (3) and 0.356 (3). The two disordered components differ from one another in the orientation of the isopropyl substituents, and both differ from the ordered molecules in the arrangement of the central propenone spacer unit, so that the crystal of (II) contains three distinct conformers. The ordered and disordered conformers each form a it C(8) chain built from a single type of C---H···O hydrogen bond but those formed by the disordered conformers differ from that formed by the ordered form.

KW - Crystal structure

KW - Synthesis

KW - Chalcones

KW - Molecular structure

KW - Molecular conformation

KW - Conformational disorder

KW - Hydrogen bonding

KW - Supramolecular assembly

U2 - 10.1107/S2056989016011592

DO - 10.1107/S2056989016011592

M3 - Article

SN - 2056-9890

VL - 72

SP - 1153

EP - 1158

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

IS - 8

ER -

The crystal structures of two chalcones: (2E)-1-(5-chlorothiophen-2-yl)-3-(2-methylphenyl)prop-2-en-1-one and (2E)-1-(anthracen-9-yl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one

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Data underpinning - The crystal structures of two chalcones: (2E)-1-(5-chlorothiophen-2-yl)-3-(2-methylphenyl)prop-2-en-1-one and (2E)-1-(anthracen-9-yl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one

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