Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-Ray Diffraction, Infrared Spectroscopy, and DFT Calculations (2024)

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Molecules

Volume 29

Issue 10

10.3390/molecules29102201

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Article

by

Julia Polak

Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-Ray Diffraction, Infrared Spectroscopy, and DFT Calculations (5)Julia Polak

1,

Julia Bąkowicz

Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-Ray Diffraction, Infrared Spectroscopy, and DFT Calculations (6)Julia Bąkowicz

2Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-Ray Diffraction, Infrared Spectroscopy, and DFT Calculations (7) and

Barbara Morzyk-Ociepa

Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-Ray Diffraction, Infrared Spectroscopy, and DFT Calculations (8)Barbara Morzyk-Ociepa

1,*Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-Ray Diffraction, Infrared Spectroscopy, and DFT Calculations (9)

1

Institute of Chemistry, Faculty of Science and Technology, Jan Dlugosz University in Czestochowa, Armii Krajowej 13/15, 42-200 Czestochowa, Poland

2

Faculty of Chemistry, Wroclaw University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wroclaw, Poland

*

Author to whom correspondence should be addressed.

Molecules 2024, 29(10), 2201; https://doi.org/10.3390/molecules29102201

Submission received: 20 April 2024/Revised: 3 May 2024/Accepted: 7 May 2024/Published: 8 May 2024

(This article belongs to the Special Issue The Design and Synthesis of Indole Derivatives and Their Metal Complexes)

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Abstract

This study presents a new 5-methoxy-1H-indole-2-carboxylic acid (MI2CA) polymorph investigated by single-crystal X-ray diffraction, infrared spectroscopy, and density functional theory (ωB97X-D) calculations employing two basis sets (6-31++G(d,p) and aug-cc-pVTZ). The compound crystallizes in the monoclinic system, space group P21/c (a = 4.0305(2) Å, b = 13.0346(6) Å, c = 17.2042(9) Å, β = 91.871(5)°, Z = 4). In the crystalline structure, the formation of cyclic dimers via double hydrogen bonds O−H⋯O between MI2CA molecules was observed. Interactions between the NH groups of the indole rings and the adjacent methoxy groups, as well as C–H⋯O contacts, significantly influence the spatial arrangement of molecules. The results from DFT calculations, including dimeric and trimeric structures, agree well with the experimental structural and spectroscopic data. Analysis of the infrared spectra confirms the conclusions drawn from X-ray diffraction studies and reveals differences between the IR spectra of the newly obtained polymorph and that reported earlier in the literature. This comprehensive study sheds some light on the MI2CA polymorphism and is important for a potential pharmacological applications of this compound.

Keywords: 5-methoxyindole-2-carboxylic acid; polymorph; crystal structure; IR spectroscopy; DFT

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MDPI and ACS Style

Polak, J.; Bąkowicz, J.; Morzyk-Ociepa, B.Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-Ray Diffraction, Infrared Spectroscopy, and DFT Calculations. Molecules 2024, 29, 2201.https://doi.org/10.3390/molecules29102201

AMA Style

Polak J, Bąkowicz J, Morzyk-Ociepa B.Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-Ray Diffraction, Infrared Spectroscopy, and DFT Calculations. Molecules. 2024; 29(10):2201.https://doi.org/10.3390/molecules29102201

Chicago/Turabian Style

Polak, Julia, Julia Bąkowicz, and Barbara Morzyk-Ociepa.2024. "Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-Ray Diffraction, Infrared Spectroscopy, and DFT Calculations" Molecules 29, no. 10: 2201.https://doi.org/10.3390/molecules29102201

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MDPI and ACS Style

Polak, J.; Bąkowicz, J.; Morzyk-Ociepa, B.Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-Ray Diffraction, Infrared Spectroscopy, and DFT Calculations. Molecules 2024, 29, 2201.https://doi.org/10.3390/molecules29102201

AMA Style

Polak J, Bąkowicz J, Morzyk-Ociepa B.Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-Ray Diffraction, Infrared Spectroscopy, and DFT Calculations. Molecules. 2024; 29(10):2201.https://doi.org/10.3390/molecules29102201

Chicago/Turabian Style

Polak, Julia, Julia Bąkowicz, and Barbara Morzyk-Ociepa.2024. "Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-Ray Diffraction, Infrared Spectroscopy, and DFT Calculations" Molecules 29, no. 10: 2201.https://doi.org/10.3390/molecules29102201

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Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-Ray Diffraction, Infrared Spectroscopy, and DFT Calculations (10)

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Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-Ray Diffraction, Infrared Spectroscopy, and DFT Calculations (2024)
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