A Study X-ray Crystal Structure of Compound 2-[Methylthio(morpholino)methylene]malononitrile, C9H11N3OS

Wedad Melad Al-Adiwish; Mabrouka Mouloud Hamza; Khairi Mohamed Hamza

doi:doi:10.11648/j.ajqcms.20190301.13

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A Study X-ray Crystal Structure of Compound 2-[Methylthio(morpholino)methylene]malononitrile, C₉H₁₁N₃OS

Wedad Melad Al-Adiwish, Mabrouka Mouloud Hamza, Khairi Mohamed Hamza

Published in American Journal of Quantum Chemistry and Molecular Spectroscopy (Volume 3, Issue 1)

Received: 28 July 2019 Accepted: 19 August 2019 Published: 2 September 2019

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Abstract

In this paper we reported the crystal structure of 2-[methylthio(morpholino)methylene]malononitrile (C₉H₁₁N₃OS). The compound was obtained by crystallization reaction between 2-(bis(methylthio)methylene)malononitrile and morpholine. The structure of compound C₉H₁₁N₃OS was identified by performing X-ray diffraction analysis. Suitable crystals were grown by slow crystallisation from ethanol for 24h. The compound C₉H₁₁N₃OS crystallized in an orthorhombic crystal system with a space group of Pna21. In the title compound, C₉H₁₁N₃OS, the two cyano groups and the morpholinyl ring adopt a cis-trans configuration of the C=C bond, showing an Z, E configuration. The morpholine ring is adopting chair conformation. In the compound C₉H₁₁N₃OS, the central fragment S1/N3/C2/C9, the morpholine ring O6/N3/O4/C5/C7/C8 and the 1,1-dicyanomethylen fragment N11/N13/C9/C10/C12 are almost planar. The central fragment makes dihedral angle of 23.11 (15)° with the 1,1-dicyano methylen fragment. The morpholine ring is twisted out of the plane of the central fragment as seen in the value of the C8—N3—C2—S1 torsional angle of 33.1 (3)°. The dihedral angle between the central fragment and the morpholine ring is 35.26 (12)°. In the crystal structure a weak intramolecular hydrogen bond C8—H(8 2)…S1 has been observed and intermolecular classical C(4)—H(41)...S(1), C(5—H(52)...S(1) and weak C(8)—(H81)...O(6) hydrogen bonds link the molecules into chains along the a axis.

Published in	American Journal of Quantum Chemistry and Molecular Spectroscopy (Volume 3, Issue 1)
DOI	10.11648/j.ajqcms.20190301.13
Page(s)	12-16
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2019. Published by Science Publishing Group

Keywords

Synthesis, Single-crystal X-ray Study, R Factor = 0.0374, wR Factor = 0.0872, Data-to-parameter Ratio = 15.0

References

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Wedad Melad Al-Adiwish, Mabrouka Mouloud Hamza, Khairi Mohamed Hamza. (2019). A Study X-ray Crystal Structure of Compound 2-[Methylthio(morpholino)methylene]malononitrile, C9H11N3OS. American Journal of Quantum Chemistry and Molecular Spectroscopy, 3(1), 12-16. https://doi.org/10.11648/j.ajqcms.20190301.13

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ACS Style

Wedad Melad Al-Adiwish; Mabrouka Mouloud Hamza; Khairi Mohamed Hamza. A Study X-ray Crystal Structure of Compound 2-[Methylthio(morpholino)methylene]malononitrile, C9H11N3OS. Am. J. Quantum Chem. Mol. Spectrosc. 2019, 3(1), 12-16. doi: 10.11648/j.ajqcms.20190301.13

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AMA Style

Wedad Melad Al-Adiwish, Mabrouka Mouloud Hamza, Khairi Mohamed Hamza. A Study X-ray Crystal Structure of Compound 2-[Methylthio(morpholino)methylene]malononitrile, C9H11N3OS. Am J Quantum Chem Mol Spectrosc. 2019;3(1):12-16. doi: 10.11648/j.ajqcms.20190301.13

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@article{10.11648/j.ajqcms.20190301.13,
  author = {Wedad Melad Al-Adiwish and Mabrouka Mouloud Hamza and Khairi Mohamed Hamza},
  title = {A Study X-ray Crystal Structure of Compound 2-[Methylthio(morpholino)methylene]malononitrile, C9H11N3OS},
  journal = {American Journal of Quantum Chemistry and Molecular Spectroscopy},
  volume = {3},
  number = {1},
  pages = {12-16},
  doi = {10.11648/j.ajqcms.20190301.13},
  url = {https://doi.org/10.11648/j.ajqcms.20190301.13},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajqcms.20190301.13},
  abstract = {In this paper we reported the crystal structure of 2-[methylthio(morpholino)methylene]malononitrile (C9H11N3OS). The compound was obtained by crystallization reaction between 2-(bis(methylthio)methylene)malononitrile and morpholine. The structure of compound C9H11N3OS was identified by performing X-ray diffraction analysis. Suitable crystals were grown by slow crystallisation from ethanol for 24h. The compound C9H11N3OS crystallized in an orthorhombic crystal system with a space group of Pna21. In the title compound, C9H11N3OS, the two cyano groups and the morpholinyl ring adopt a cis-trans configuration of the C=C bond, showing an Z, E configuration. The morpholine ring is adopting chair conformation. In the compound C9H11N3OS, the central fragment S1/N3/C2/C9, the morpholine ring O6/N3/O4/C5/C7/C8 and the 1,1-dicyanomethylen fragment N11/N13/C9/C10/C12 are almost planar. The central fragment makes dihedral angle of 23.11 (15)° with the 1,1-dicyano methylen fragment. The morpholine ring is twisted out of the plane of the central fragment as seen in the value of the C8—N3—C2—S1 torsional angle of 33.1 (3)°. The dihedral angle between the central fragment and the morpholine ring is 35.26 (12)°. In the crystal structure a weak intramolecular hydrogen bond C8—H(8 2)…S1 has been observed and intermolecular classical C(4)—H(41)...S(1), C(5—H(52)...S(1) and weak C(8)—(H81)...O(6) hydrogen bonds link the molecules into chains along the a axis.},
 year = {2019}
}

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TY  - JOUR
T1  - A Study X-ray Crystal Structure of Compound 2-[Methylthio(morpholino)methylene]malononitrile, C9H11N3OS
AU  - Wedad Melad Al-Adiwish
AU  - Mabrouka Mouloud Hamza
AU  - Khairi Mohamed Hamza
Y1  - 2019/09/02
PY  - 2019
N1  - https://doi.org/10.11648/j.ajqcms.20190301.13
DO  - 10.11648/j.ajqcms.20190301.13
T2  - American Journal of Quantum Chemistry and Molecular Spectroscopy
JF  - American Journal of Quantum Chemistry and Molecular Spectroscopy
JO  - American Journal of Quantum Chemistry and Molecular Spectroscopy
SP  - 12
EP  - 16
PB  - Science Publishing Group
SN  - 2994-7308
UR  - https://doi.org/10.11648/j.ajqcms.20190301.13
AB  - In this paper we reported the crystal structure of 2-[methylthio(morpholino)methylene]malononitrile (C9H11N3OS). The compound was obtained by crystallization reaction between 2-(bis(methylthio)methylene)malononitrile and morpholine. The structure of compound C9H11N3OS was identified by performing X-ray diffraction analysis. Suitable crystals were grown by slow crystallisation from ethanol for 24h. The compound C9H11N3OS crystallized in an orthorhombic crystal system with a space group of Pna21. In the title compound, C9H11N3OS, the two cyano groups and the morpholinyl ring adopt a cis-trans configuration of the C=C bond, showing an Z, E configuration. The morpholine ring is adopting chair conformation. In the compound C9H11N3OS, the central fragment S1/N3/C2/C9, the morpholine ring O6/N3/O4/C5/C7/C8 and the 1,1-dicyanomethylen fragment N11/N13/C9/C10/C12 are almost planar. The central fragment makes dihedral angle of 23.11 (15)° with the 1,1-dicyano methylen fragment. The morpholine ring is twisted out of the plane of the central fragment as seen in the value of the C8—N3—C2—S1 torsional angle of 33.1 (3)°. The dihedral angle between the central fragment and the morpholine ring is 35.26 (12)°. In the crystal structure a weak intramolecular hydrogen bond C8—H(8 2)…S1 has been observed and intermolecular classical C(4)—H(41)...S(1), C(5—H(52)...S(1) and weak C(8)—(H81)...O(6) hydrogen bonds link the molecules into chains along the a axis.
VL  - 3
IS  - 1
ER  -

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Author Information

Wedad Melad Al-Adiwish

Department Chemistry, Faculty of Science, Zawia University, Zawia, Libya
Mabrouka Mouloud Hamza

Department Chemistry, Faculty of Education, Zawia University, Zawia, Libya
Khairi Mohamed Hamza

Department Chemistry, Faculty of Education, Zawia University, Zawia, Libya

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Wedad Melad Al-Adiwish, Mabrouka Mouloud Hamza, Khairi Mohamed Hamza. (2019). A Study X-ray Crystal Structure of Compound 2-[Methylthio(morpholino)methylene]malononitrile, C9H11N3OS. American Journal of Quantum Chemistry and Molecular Spectroscopy, 3(1), 12-16. https://doi.org/10.11648/j.ajqcms.20190301.13

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ACS Style

Wedad Melad Al-Adiwish; Mabrouka Mouloud Hamza; Khairi Mohamed Hamza. A Study X-ray Crystal Structure of Compound 2-[Methylthio(morpholino)methylene]malononitrile, C9H11N3OS. Am. J. Quantum Chem. Mol. Spectrosc. 2019, 3(1), 12-16. doi: 10.11648/j.ajqcms.20190301.13

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AMA Style

Wedad Melad Al-Adiwish, Mabrouka Mouloud Hamza, Khairi Mohamed Hamza. A Study X-ray Crystal Structure of Compound 2-[Methylthio(morpholino)methylene]malononitrile, C9H11N3OS. Am J Quantum Chem Mol Spectrosc. 2019;3(1):12-16. doi: 10.11648/j.ajqcms.20190301.13

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@article{10.11648/j.ajqcms.20190301.13,
  author = {Wedad Melad Al-Adiwish and Mabrouka Mouloud Hamza and Khairi Mohamed Hamza},
  title = {A Study X-ray Crystal Structure of Compound 2-[Methylthio(morpholino)methylene]malononitrile, C9H11N3OS},
  journal = {American Journal of Quantum Chemistry and Molecular Spectroscopy},
  volume = {3},
  number = {1},
  pages = {12-16},
  doi = {10.11648/j.ajqcms.20190301.13},
  url = {https://doi.org/10.11648/j.ajqcms.20190301.13},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajqcms.20190301.13},
  abstract = {In this paper we reported the crystal structure of 2-[methylthio(morpholino)methylene]malononitrile (C9H11N3OS). The compound was obtained by crystallization reaction between 2-(bis(methylthio)methylene)malononitrile and morpholine. The structure of compound C9H11N3OS was identified by performing X-ray diffraction analysis. Suitable crystals were grown by slow crystallisation from ethanol for 24h. The compound C9H11N3OS crystallized in an orthorhombic crystal system with a space group of Pna21. In the title compound, C9H11N3OS, the two cyano groups and the morpholinyl ring adopt a cis-trans configuration of the C=C bond, showing an Z, E configuration. The morpholine ring is adopting chair conformation. In the compound C9H11N3OS, the central fragment S1/N3/C2/C9, the morpholine ring O6/N3/O4/C5/C7/C8 and the 1,1-dicyanomethylen fragment N11/N13/C9/C10/C12 are almost planar. The central fragment makes dihedral angle of 23.11 (15)° with the 1,1-dicyano methylen fragment. The morpholine ring is twisted out of the plane of the central fragment as seen in the value of the C8—N3—C2—S1 torsional angle of 33.1 (3)°. The dihedral angle between the central fragment and the morpholine ring is 35.26 (12)°. In the crystal structure a weak intramolecular hydrogen bond C8—H(8 2)…S1 has been observed and intermolecular classical C(4)—H(41)...S(1), C(5—H(52)...S(1) and weak C(8)—(H81)...O(6) hydrogen bonds link the molecules into chains along the a axis.},
 year = {2019}
}

Copy | Download

TY  - JOUR
T1  - A Study X-ray Crystal Structure of Compound 2-[Methylthio(morpholino)methylene]malononitrile, C9H11N3OS
AU  - Wedad Melad Al-Adiwish
AU  - Mabrouka Mouloud Hamza
AU  - Khairi Mohamed Hamza
Y1  - 2019/09/02
PY  - 2019
N1  - https://doi.org/10.11648/j.ajqcms.20190301.13
DO  - 10.11648/j.ajqcms.20190301.13
T2  - American Journal of Quantum Chemistry and Molecular Spectroscopy
JF  - American Journal of Quantum Chemistry and Molecular Spectroscopy
JO  - American Journal of Quantum Chemistry and Molecular Spectroscopy
SP  - 12
EP  - 16
PB  - Science Publishing Group
SN  - 2994-7308
UR  - https://doi.org/10.11648/j.ajqcms.20190301.13
AB  - In this paper we reported the crystal structure of 2-[methylthio(morpholino)methylene]malononitrile (C9H11N3OS). The compound was obtained by crystallization reaction between 2-(bis(methylthio)methylene)malononitrile and morpholine. The structure of compound C9H11N3OS was identified by performing X-ray diffraction analysis. Suitable crystals were grown by slow crystallisation from ethanol for 24h. The compound C9H11N3OS crystallized in an orthorhombic crystal system with a space group of Pna21. In the title compound, C9H11N3OS, the two cyano groups and the morpholinyl ring adopt a cis-trans configuration of the C=C bond, showing an Z, E configuration. The morpholine ring is adopting chair conformation. In the compound C9H11N3OS, the central fragment S1/N3/C2/C9, the morpholine ring O6/N3/O4/C5/C7/C8 and the 1,1-dicyanomethylen fragment N11/N13/C9/C10/C12 are almost planar. The central fragment makes dihedral angle of 23.11 (15)° with the 1,1-dicyano methylen fragment. The morpholine ring is twisted out of the plane of the central fragment as seen in the value of the C8—N3—C2—S1 torsional angle of 33.1 (3)°. The dihedral angle between the central fragment and the morpholine ring is 35.26 (12)°. In the crystal structure a weak intramolecular hydrogen bond C8—H(8 2)…S1 has been observed and intermolecular classical C(4)—H(41)...S(1), C(5—H(52)...S(1) and weak C(8)—(H81)...O(6) hydrogen bonds link the molecules into chains along the a axis.
VL  - 3
IS  - 1
ER  -

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