Sains Malaysiana 48(9)(2019): 1879–1885

http://dx.doi.org/10.17576/jsm-2019-4809-08

 

Crystal Structure, Hirshfeld Analysis and DFT Study of 6,7-Dimethoxy-3-[(5-Chloro-1,3,3-Trimethylindolin-2-Ylidene)Methyl]Isobenzofuran-1(3h)-One

(Struktur Hablur, Analisis Hirshfeld dan Kajian DFT 6,7- Dimetoksi -3-[(5-Kloro-1,3,3-Trimetillindolin-2- ilidena)] Isobenzofuran-1(3h)-one)

 

SUHAILA SAPARI1, EMMA IZZATI ZAKARIAH1, NORAISYAH ABDUL KADIR JILANI1, SHERYN WONG1, MOHAMMAD FADZLEE NGATIMAN2 & SITI AISHAH HASBULLAH1*

 

1Centre of Advanced Materials and Renewable Resources, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor Darul Ehsan, Malaysia

 

2Center for Research and Instrumentation Management, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor Darul Ehsan, Malaysia

 

Diserahkan: 7 Mei 2019/Diterima: 21 Jun 2019

 

ABSTRACT

The coupling reaction of 5-chloro-1,3,3-methylenindoline with 6-formyl-2,3-dimethoxy benzoic acid under solvent-free microwave irradiation gave of 6,7-dimethoxy-3-[(5-chloro-1,3,3-trimethylindolin-2-ylidene)methyl]isobenzofuran-1(3H)-one, C22H22ClNO4 in high yield. The molecular structure consists of indoline system (C1-C8/N1) and isobenzofuran system (C10-C17/O1) connected by the enamine carbon. The title compound is crystallised in P21/n space group, Z’=4 with two independent molecules in centrosymmetric dimer. By using Hirshfeld surface and two-dimensional fingerprint plots, the presence of short intermolecular interactions and π-π stacking in the crystal structure were analysed. The DFT study is performed by comparing the calculation data with the X-ray data and analysing the HOMO and LUMO value, which gave -0.26952 a.u. and -0.17760 a.u., respectively.

 

Keywords: Crystal; DFT; Hirshfeld analysis; phthalide; synthesis

 

ABSTRAK

Tindak balas pergandingan antara 5-kloro-1,3,3-metilenindolina dengan 6-formil-2,3-dimetoksi benzoik asid dalam keadaan bebas pelarut di bawah sinaran gelombang menghasilkan 6,7-dimetoksi-3-[(5-kloro-1,3,3-trimetilindolin-2-ilidena) metil]isobenzofuran-1(3H)-one, C22H22ClNO4 dalam hasil yang tinggi. Struktur molekul terdiri daripada sistem indolina (C1-C8/N1) dan sistem isobenzofuran (C10-C17/O1) yang disambungkan oleh karbon enamina. Sebatian ini menghablur dalam kumpulan ruang P21/n, Z’=4 dengan dua molekul bebas dalam dimer yang berpusat simetri. Dengan menggunakan permukaan Hirshfeld dan plot pengecaman dua dimensi, kehadiran interaksi intermolekul yang pendek dan susunan π-π dalam struktur hablur dianalisis. Kajian DFT dilakukan dengan membandingkan data perhitungan dengan data sinar X dan menganalisis nilai HOMO dan LUMO, yang masing-masing memberi -0.26952 a.u. dan -0.17760 a.u.

 

Kata kunci: Analisis Hirshfeld; DFT; hablur; phtalida; sintesis  

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*Pengarang untuk surat-menyurat; email: aishah80@ukm.edu.my

 

 

 

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