Crystal Structure of 3-Chloromethyl-(3-phenyl-oxiranyl)phenyl Methanone: New Monoclinic Polymorph

Muhammad Nadeem Arshad; Abdullah M. Asiri; Khalid A. Alamry; Salih S. Al-Juaid; Sher Bahadar Khan; Tanveer Hussain Bokhari; Muhammad Shafiq

doi:10.14233/ajchem.2014.16095

Issue

Vol. 26 No. 9 (2014): Vol 26 Issue 9

Issue Published : April 28, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Crystal Structure of 3-Chloromethyl-(3-phenyl-oxiranyl)phenyl Methanone: New Monoclinic Polymorph

https://doi.org/10.14233/ajchem.2014.16095

Muhammad Nadeem Arshad

Chemistry Department, King Abdulaziz University, Jeddah 21589, Saudi Arabia; Center of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, Jeddah 21589 Saudi Arabia

Abdullah M. Asiri

Chemistry Department, King Abdulaziz University, Jeddah 21589, Saudi Arabia; Center of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, Jeddah 21589 Saudi Arabia

Khalid A. Alamry

Chemistry Department, King Abdulaziz University, Jeddah 21589, Saudi Arabia

Salih S. Al-Juaid

Chemistry Department, King Abdulaziz University, Jeddah 21589, Saudi Arabia

Sher Bahadar Khan

Chemistry Department, King Abdulaziz University, Jeddah 21589, Saudi Arabia; Center of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, Jeddah 21589 Saudi Arabia

Tanveer Hussain Bokhari

Department of Chemistry, Government College University Faisalabad, Faisalabad, Pakistan

Muhammad Shafiq

Department of Chemistry, Government College University Faisalabad, Faisalabad, Pakistan

Corresponding Author(s) : Muhammad Nadeem Arshad

mnachemist@hotmail.com

Asian Journal of Chemistry, Vol. 26 No. 9 (2014): Vol 26 Issue 9
Article Published : April 29, 2014

Abstract

The compound, 3-chloromethyl-(3-phenyl-oxiranyl)phenyl methanone [m.f. C₁₆H₁₃O₂Cl] was a self-condensation product of phenacyl chloride where the reaction carried out in ethanol medium using inorganic base. This was crystalized in monoclinic with space group P2₁/c (no. 14), a = 10.1312 (2) Å, b = 11.7728 Å, c = 11.8566 Å, V = 1344.07 Å³, Z = 4 and r_calc. = 1.348 mg/mm³. The dihedral angle between two aromatic rings is 73.46 (5). The epoxide ring is oriented at dihedral angles of 62.12 (9°) and 60.87 (7°) with respect to the phenyl and benzoyl rings. The non-classical intermolecular hydrogen bonding of C-H···O type has been observed in the crystal structure of molecule.

Keywords

3-Chloromethyl-3-phenyl-oxiranyl)phenyl methanone Crystal structure New polymorph

Nadeem Arshad, M., M. Asiri, A., A. Alamry, K., S. Al-Juaid, S., Bahadar Khan, S., Hussain Bokhari, T., & Shafiq, M. (2014). Crystal Structure of 3-Chloromethyl-(3-phenyl-oxiranyl)phenyl Methanone: New Monoclinic Polymorph. Asian Journal of Chemistry, 26(9), 2715–2717. https://doi.org/10.14233/ajchem.2014.16095

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References

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References

R.O.C. Norman and C.M. Coxon, Principles of Organic Synthesis, CRC Press, New York (2009).

R. Noyori, Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons, New York (1994).

F.W. Bachelor and R.K. Bansal, J. Org. Chem., 34, 3600 (1969); doi:10.1021/jo01263a082.

R.K. Boeckman Jr., T.J. Clark and B.C. Shook, Helv. Chim. Acta, 85, 4532 (2002); doi:10.1002/hlca.200290026.

A. Jonczyk and K. Michalski, Synlett, 1703 (2002); doi:10.1055/s-2002-34223.

L.W. Xu, J.W. Li, S.L. Zhou and C.G. Xia, New J. Chem., 28, 183 (2004); doi:10.1039/b312047c.

Z.-T. Wang, L.-W. Xu, C.-G. Xia and H.-Q. Wang, Helv. Chim. Acta, 87, 1958 (2004); doi:10.1002/hlca.200490177.

O. Miyata, T. Shinada, I. Ninomiya and T. Naito, Tetrahedron, 53, 2421 (1997); doi:10.1016/S0040-4020(96)01191-X.

B.M. Adger, J.V. Barkley, S. Bergeron, M.W. Cappi, B.E. Flowerdew, M.P. Jackson, R. McCague, T.C. Nugent and S.M. Roberts, J. Chem. Soc., Perkin Trans. I, 3501 (1997); doi:10.1039/a704413e.

C. Lauret, Tetrahedron Asymm., 12, 2359 (2001); doi:10.1016/S0957-4166(01)00412-8.

J.R. Flisak, K.J. Gombatz, M.M. Holmes, A.A. Jarmas, I. Lantos, W.L. Mendelson, V.J. Novack, J.J. Remich and L. Snyder, J. Org. Chem., 58, 6247 (1993); doi:10.1021/jo00075a019.

P.C. Ray and S.M. Roberts, J. Chem. Soc., Perkin Trans. 1, 149 (2001); doi:10.1039/b007100p.

T. Nemoto, T. Ohshima and M. Shibasaki, Tetrahedron Lett., 41, 9569 (2000); doi:10.1016/S0040-4039(00)01702-0.

Agilent, CrysAlis PRO, Agilent Technologies, Yarnton, England (2012).

L.J. Barbour, J. Supramol. Chem., 1, 189 (2001); doi:10.1016/S1472-7862(02)00030-8.

G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008); doi:10.1107/S0108767307043930.

A.L. Spek, Acta Crystallogr. D Biol. Crystallogr., 65, 148 (2009); doi:10.1107/S090744490804362X.

L.J. Farrugia, J. Appl. Cryst., 45, 849 (2012); doi:10.1107/S0021889812029111.

I.J. Bruno, J.C. Cole, P.R. Edgington, M. Kessler, C.F. Macrae, P. McCabe, J. Pearson and R. Taylor, Acta Crystallogr., B58, 389 (2002).

P. Bako, E. Czinege, T. Bako, M. Czugler and L. Toke, Tetrahedron Asymmetry, 10, 4539 (1999); doi:10.1016/S0957-4166(99)00485-1.

Issue

Vol. 26 No. 9 (2014): Vol 26 Issue 9

Crystal Structure of 3-Chloromethyl-(3-phenyl-oxiranyl)phenyl Methanone: New Monoclinic Polymorph

Corresponding Author(s) : Muhammad Nadeem Arshad

Abstract

Keywords

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