European Journal of Chemistry

X-ray crystal structure analysis of 5-bromospiro[indoline-3,7'-pyrano[3,2-C:5,6-C']dichromene]-2,6',8'-trione

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Varun Sharma
Bubun Banerjee
Gurpreet Kaur
Vivek Kumar Gupta

Abstract

An analog of spirooxindole[pyrano-bis-2H-l-benzopyran] derivatives namely 5-bromospiro [indoline-3,7'-pyrano[3,2-c:5,6-c']dichromene]-2,6',8'-trione was synthesized via one-pot pseudo three-component reaction of one equivalent of 5-bromoisatin and two equivalents of 4-hydroxycoumarin using mandelic acid as a naturally occurring organo catalyst in aqueous ethanol under reflux conditions. The synthesized compound was characterized by FT-IR, 1H NMR, 13C NMR, and HRMS data. Crystal structure was determined by using single X-ray crystallography technique. It was found that the crystals are triclinic with space group P-1, C108H60Br4N4O29S2: a = 11.8333(6) Å, b = 12.8151(6) Å, c = 17.1798(8) Å, α = 77.317(4)°, β = 74.147(4)°, γ = 66.493(5)°, = 2280.0(2) Å3, Z = 1, T = 149.99(10) K, μ(MoKα) = 1.902 mm-1, Dcalc = 1.647 g/cm3, 11545 reflections measured (3.836° ≤ 2Θ ≤ 50.998°), 8310 unique (Rint = 0.0488, Rsigma = 0.0875) which were used in all calculations. The final R1 was 0.0622 (I > 2σ(I)) and wR2 was 0.1994 (all data). The crystal structure was solved by direct methods and refined by full-matrix least-squares procedure to a final R-value of 0.0622 for 6264 observed reflections. The crystal structure was stabilized by an elaborate system of N-H···O, O-H···O, C-H···π, and π···π interactions involving solvent molecules to form supramolecular structure.


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Sharma, V.; Banerjee, B.; Kaur, G.; Gupta, V. K. X-Ray Crystal Structure Analysis of 5-bromospiro[indoline-3,7’-pyrano[3,2-C:5,6-C’]dichromene]-2,6’,8’-Trione. Eur. J. Chem. 2021, 12, 187-191.

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References

[1]. Banerjee, B. Chem. Select 2017, 2 (23), 6744-6757.
https://doi.org/10.1002/slct.201701441

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

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

[4]. Banerjee, B.; Kaur, G. Curr. Microw. Chem. 2020, 7 (1), 5-22.
https://doi.org/10.2174/2213335607666200226102010

[5]. Kaur, G.; Bala, K.; Devi, S.; Banerjee, B. Curr. Green Chem. 2018, 5 (3), 150-167.
https://doi.org/10.2174/2213346105666181001113413

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

[7]. Almansour, A. I.; Kumar, R. S.; Arumugam, N.; Vishnupriya, R.; Suresh, J. Acta Crystallogr. Sect. E Struct. Rep. Online 2012, 68 (4), o1194-o1194.
https://doi.org/10.1107/S1600536812000827

[8]. Almansour, A. I.; Kumar, R. S.; Arumugam, N.; Devi Shree, P.; Suresh, J. Acta Crystallogr. Sect. E Struct. Rep. Online 2012, 68 (3), o744-o744.
https://doi.org/10.1107/S1600536812006332

[9]. 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

[10]. 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

[11]. 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

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

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

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

[15]. Spek, A. L. Acta Crystallogr. D Biol. Crystallogr. 2009, 65, 148-155.
https://doi.org/10.1107/S090744490804362X

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

[17]. 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

Supporting Agencies

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