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

Received: 7 May 2019/Accepted: 21 June 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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*Corresponding author; email: aishah80@ukm.edu.my