European Journal of Chemistry 2021, 12(4), 382-388 | doi: https://doi.org/10.5155/eurjchem.12.4.382-388.2141 | Get rights and content

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Synthesis, X-ray crystal structure, Hirshfeld surface analysis, and molecular docking studies of DMSO/H2O solvate of 5-chlorospiro[indoline-3,7'-pyrano[3,2-c:5,6-c']dichromene]-2,6',8'-trione


Varun Sharma (1) orcid , Bubun Banerjee (2) orcid , Aditi Sharma (3) orcid , Vivek Kumar Gupta (4,*) orcid

(1) Department of Physics, University of Jammu, Jammu Tawi-180006, India
(2) Department of Chemistry, Akal University, Talwandi Sabo, Bathinda, Punjab-151302, India
(3) Department of Chemistry, Akal University, Talwandi Sabo, Bathinda, Punjab-151302, India
(4) Department of Physics, University of Jammu, Jammu Tawi-180006, India
(*) Corresponding Author

Received: 08 Jul 2021 | Revised: 11 Aug 2021 | Accepted: 28 Aug 2021 | Published: 31 Dec 2021 | Issue Date: December 2021

Abstract


The title compound, 5-chlorospiro[indoline-3,7'-pyrano[3,2-c:5,6-c']dichromene]-2,6',8'-trione was synthesized via one-pot pseudo three-component reaction between one equivalent of 5-chloroisatin and two equivalents of 4-hydroxycoumarin using mandelic acid as catalyst in aqueous ethanol at 110 °C. The synthesized compound was characterized by FT-IR, 1H NMR, and HRMS techniques. Single crystals were grown for crystal structure determination by using single X-ray crystallography technique. It was found that the crystals are triclinic with space group P-1 and Z = 1. The crystal structure was solved by direct method and refined by full-matrix least-squares procedures to a final R-value of 0.0688 for 6738 observed reflections. The crystal structure was stabilized by elaborate system of O-H···O, N-H···O, and C-H···O interactions with the formation of supramolecular structures. 3D Hirshfeld surfaces and allied 2D fingerprint plots were analyzed for molecular interactions. Molecular docking studies have been performed to get insights into the inhibition property of this molecule for Human topoisomerase IIα.


Keywords


Indoline; Mandelic acid; Direct methods; Hydrogen bonding; X-ray crystallography; Hirshfeld surface analysis

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DOI: 10.5155/eurjchem.12.4.382-388.2141

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Funding information


University of Jammu, Jammu, India, Rashtriya Uchchatar Shiksha Abhiyan (RUSA) 2.0 Project. (Ref. No: RUSA/JU/2/ 2019-20/111/3588-3636).

References


[1]. Banerjee, B.; Kaur, G.; Kaur, N. Curr. Org. Chem. 2021, 25 (1), 209-222.
https://doi.org/10.2174/1385272824999201019162655

[2]. Kaur, G.; Moudgil, R.; Shamim, M.; Gupta, V. K.; Banerjee, B. Synth. Commun. 2021, 51 (7), 1100-1120.
https://doi.org/10.1080/00397911.2020.1870043

[3]. Brahmachari, G.; Banerjee, B. ACS Sustain. Chem. Eng. 2014, 2 (3), 411-422.
https://doi.org/10.1021/sc400312n

[4]. Kaur, G.; Singh, D.; Singh, A.; Banerjee, B. Synth. Commun. 2021, 51 (7), 1045-1057.

[5]. Sharma, V.; Kaur, G.; Singh, A.; Banerjee, B.; Gupta, V. K. Crystallogr. Rep. 2020, 65 (7), 1195-1201.
https://doi.org/10.1134/S1063774520070172

[6]. Parthasarathy, K.; Praveen, C.; Saranraj, K.; Balachandran, C.; Kumar, P. S. Med. Chem. Res. 2016, 25 (10), 2155-2170.
https://doi.org/10.1007/s00044-016-1645-4

[7]. Sharma, V.; Banerjee, B.; Kaur, G.; Gupta, V. K. Eur. J. Chem. 2021, 12 (2), 187-191.
https://doi.org/10.5155/eurjchem.12.2.187-191.2086

[8]. Kaur, G.; Singh, A.; Kaur, N.; Banerjee, B. Synth. Commun. 2021, 51 (7), 1121-1131.
https://doi.org/10.1080/00397911.2021.1873383

[9]. Banik, B. K.; Banerjee, B.; Kaur, G.; Saroch, S.; Kumar, R. Molecules 2020, 25 (24), 5918.
https://doi.org/10.3390/molecules25245918

[10]. Banerjee, B. Curr. Org. Chem. 2018, 22 (3), 208-233.
https://doi.org/10.2174/1385272821666170703123129

[11]. Banerjee, B.; Bhardwaj, V.; Kaur, A.; Kaur, G.; Singh, A. Curr. Org. Chem. 2020, 23 (28), 3191-3205.
https://doi.org/10.2174/1385272823666191121144758

[12]. Banerjee, B.; Brahmachari, G. J. Chem. Res. 2014, 38 (12), 745-750.
https://doi.org/10.3184/174751914X14177132210020

[13]. Brahmachari, G.; Banerjee, B. ACS Sustain. Chem. Eng. 2014, 2 (12), 2802-2812.
https://doi.org/10.1021/sc500575h

[14]. Brahmachari, G.; Banerjee, B. Asian J. Org. Chem. 2016, 5 (2), 271-286.
https://doi.org/10.1002/ajoc.201500465

[15]. Kaur, G.; Singh, A.; Bala, K.; Devi, M.; Kumari, A.; Devi, S.; Devi, R.; Gupta, V. K.; Banerjee, B. Curr. Org. Chem. 2019, 23 (16), 1778-1788.
https://doi.org/10.2174/1385272822666190924182538

[16]. Singh, A.; Kaur, G.; Kaur, A.; Gupta, V. K.; Banerjee, B. Curr. Green Chem. 2020, 7 (1), 128-140.
https://doi.org/10.2174/2213346107666200228125715

[17]. Kaur, G.; Shamim, M.; Bhardwaj, V.; Gupta, V. K.; Banerjee, B. Synth. Commun. 2020, 50 (10), 1545-1560.
https://doi.org/10.1080/00397911.2020.1745844

[18]. Kaur, G.; Kumar, R.; Saroch, S.; Gupta, V. K.; Banerjee, B. Curr. Organocatalysis 2021, 8 (1), 147-159.
https://doi.org/10.2174/2213337207999200713145440

[19]. Sheldrick, G. M. Acta Crystallogr. A Found. Adv. 2015, 71 (Pt 1), 3-8.
https://doi.org/10.1107/S2053273314026370

[20]. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30 (5), 565-565.
https://doi.org/10.1107/S0021889897003117

[21]. Nardelli, M. J. Appl. Crystallogr. 1995, 28 (5), 659-659.
https://doi.org/10.1107/S0021889895007138

[22]. Spek, A. L. Acta Crystallogr. D Biol. Crystallogr. 2009, 65 (Pt 2), 148-155.
https://doi.org/10.1107/S090744490804362X

[23]. Spackman, P. R.; Turner, M. J.; McKinnon, J. J.; Wolff, S. K.; Grimwood, D. J.; Jayatilaka, D.; Spackman, M. A. J. Appl. Crystallogr. 2021, 54 (Pt 3), 1006-1011.
https://doi.org/10.1107/S1600576721002910

[24]. Wei, H.; Ruthenburg, A. J.; Bechis, S. K.; Verdine, G. L. J. Biol. Chem. 2005, 280 (44), 37041-37047.
https://doi.org/10.1074/jbc.M506520200

[25]. Discovery Studio: Dassault Systems BIOVIA, Discovery Studio Modelling Environment, Release 4.5, Dassault Systems: San Diego, 2015. From

[26]. Farrugia, L. J. J. Appl. Crystallogr. 2012, 45 (4), 849-854.
https://doi.org/10.1107/S0021889812029111

[27]. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, 12, S1-S19.
https://doi.org/10.1039/p298700000s1

[28]. Almansour, A. I.; Kumar, R. S.; Arumugam, N.; Kanagalaksmi, S.; Suresh, J. Acta Crystallogr. Sect. E Struct. Rep. Online 2012, 68 (Pt 4), o1172.
https://doi.org/10.1107/S1600536812000827

[29]. Spackman, M. A.; Jayatilaka, D. CrystEngComm 2009, 11 (1), 19-32.
https://doi.org/10.1039/B818330A

[30]. Miller, G. J. Angew. Chem. Weinheim Bergstr. Ger. 1989, 101 (11), 1570-1571.
https://doi.org/10.1002/ange.19891011137

[31]. Hoffmann, R. Solids and Surfaces: A Chemist's View of Bonding in Extended Structures; VCH, 1988.
https://doi.org/10.21236/ADA196638

[32]. McKinnon, J. J.; Mitchell, A. S.; Spackman, M. A. Chemistry 1998, 4 (11), 2136-2141.
https://doi.org/10.1002/(SICI)1521-3765(19981102)4:11<2136::AID-CHEM2136>3.0.CO;2-G


Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Sharma, V.; Banerjee, B.; Sharma, A.; Gupta, V. Eur. J. Chem. 2021, 12(4), 382-388. doi:10.5155/eurjchem.12.4.382-388.2141
Sharma, V.; Banerjee, B.; Sharma, A.; Gupta, V. Synthesis, X-ray crystal structure, Hirshfeld surface analysis, and molecular docking studies of DMSO/H2O solvate of 5-chlorospiro[indoline-3,7'-pyrano[3,2-c:5,6-c']dichromene]-2,6',8'-trione. Eur. J. Chem. 2021, 12(4), 382-388. doi:10.5155/eurjchem.12.4.382-388.2141
Sharma, V., Banerjee, B., Sharma, A., & Gupta, V. (2021). Synthesis, X-ray crystal structure, Hirshfeld surface analysis, and molecular docking studies of DMSO/H2O solvate of 5-chlorospiro[indoline-3,7'-pyrano[3,2-c:5,6-c']dichromene]-2,6',8'-trione. European Journal of Chemistry, 12(4), 382-388. doi:10.5155/eurjchem.12.4.382-388.2141
Sharma, Varun, Bubun Banerjee, Aditi Sharma, & Vivek Kumar Gupta. "Synthesis, X-ray crystal structure, Hirshfeld surface analysis, and molecular docking studies of DMSO/H2O solvate of 5-chlorospiro[indoline-3,7'-pyrano[3,2-c:5,6-c']dichromene]-2,6',8'-trione." European Journal of Chemistry [Online], 12.4 (2021): 382-388. Web. 22 May. 2022
Sharma, Varun, Banerjee, Bubun, Sharma, Aditi, AND Gupta, Vivek. "Synthesis, X-ray crystal structure, Hirshfeld surface analysis, and molecular docking studies of DMSO/H2O solvate of 5-chlorospiro[indoline-3,7'-pyrano[3,2-c:5,6-c']dichromene]-2,6',8'-trione" European Journal of Chemistry [Online], Volume 12 Number 4 (31 December 2021)

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