European Journal of Chemistry 2022, 13(2), 230-233 | doi: https://doi.org/10.5155/eurjchem.13.2.230-233.2256 | Get rights and content

Issue cover




Crossmark

  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Phenazine and 10H-phenothiazine cocrystal stabilized by N-H···N and C-H···S hydrogen bonds


Tahir Mehmood (1) orcid , Bhumiben Chandubhai Patel (2) orcid , Jayarama Prakasha Reddy (3,*) orcid

(1) Department of Chemistry, School of Sciences, Indrashil University, Rajpur, Gujarat 382740, India
(2) Department of Chemistry, School of Sciences, Indrashil University, Rajpur, Gujarat 382740, India
(3) Department of Chemistry, School of Sciences, Indrashil University, Rajpur, Gujarat 382740, India
(*) Corresponding Author

Received: 09 Mar 2022 | Revised: 23 Apr 2022 | Accepted: 27 Apr 2022 | Published: 30 Jun 2022 | Issue Date: June 2022

Abstract


A 1:1 co-crystal of phenazine and phenothiazine was prepared. The crystal structure was determined by using a single crystal X-ray crystallography technique. Analysis of the crystal revealed that the molecular complex crystallizes in monoclinic P21/n space group, C12H8N2·C12H9NS, a = 9.068(2) Å, b = 8.872(2) Å, c = 23.935(4) Å, β = 92.16(4)°, = 1924.1(6) Å3, Z = 4, T = 293(2) K, μ(MoKα) = 0.182 mm-1, Dcalc = 1.310 g/cm3, 8057 reflections measured (3.4° ≤ 2Θ ≤ 46.54°), 2751 unique (Rint = 0.0559, Rsigma = 0.0618) which were used in all calculations. The final R1 was 0.0548 (>2sigma(I)) and wR2 was 0.1029 (all data). The molecules recognize each other through N-H···N and C-H···N hydrogen bonds, thus producing a tetramer unit. These units further interact with one another via C-H···S hydrogen bonds.


Keywords


Co-crystal; Phenazine; Phenothiazine; Hydrogen bonding; X-ray crystallography; Supramolecular assembly

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.13.2.230-233.2256

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 107 times | icon graph PDF Article downloaded 30 times

Funding information


Scheme of Developing High Quality Research (SHODH), Government of Gujarat, India.

References


[1]. Gellman, S. H. Foldamers: A manifesto. Acc. Chem. Res. 1998, 31, 173-180.
https://doi.org/10.1021/ar960298r

[2]. Selvanathan, S.; Peters, M. V.; Schwarz, J.; Hecht, S.; Grill, L. Formation and manipulation of discrete supramolecular azobenzene assemblies. Appl. Phys. A Mater. Sci. Process. 2008, 93, 247-252.
https://doi.org/10.1007/s00339-008-4827-1

[3]. Prabhakaran, P.; Puranik, V. G.; Chandran, J. N.; Rajamohanan, P. R.; Hofmann, H.-J.; Sanjayan, G. J. Novel foldamer structural architecture from cofacial aromatic building blocks. Chem. Commun. (Camb.) 2009, 3446-3448.
https://doi.org/10.1039/b822113h

[4]. Cuccia, L. A.; Lehn, J. M.; Homo, J. C.; Schmutz, M. Encoded helical self-organization and self-assembly into helical fibers of an oligoheterocyclic pyridine - pyridazine molecular strand. Angew. Chem. Int. Ed Engl. 2000, 39, 233-237.
https://doi.org/10.1002/(SICI)1521-3773(20000103)39:1<233::AID-ANIE233>3.0.CO;2-R

[5]. Ramesh, V. V. E.; Roy, A.; Vijayadas, K. N.; Kendhale, A. M.; Prabhakaran, P.; Gonnade, R.; Puranik, V. G.; Sanjayan, G. J. Conformationally rigid aromatic amino acids as potential building blocks for abiotic foldamers. Org. Biomol. Chem. 2011, 9, 367-369.
https://doi.org/10.1039/C0OB00593B

[6]. Ziach, K.; Chollet, C.; Parissi, V.; Prabhakaran, P.; Marchivie, M.; Corvaglia, V.; Bose, P. P.; Laxmi-Reddy, K.; Godde, F.; Schmitter, J.-M.; Chaignepain, S.; Pourquier, P.; Huc, I. Single helically folded aromatic oligoamides that mimic the charge surface of double-stranded B-DNA. Nat. Chem. 2018, 10, 511-518.
https://doi.org/10.1038/s41557-018-0018-7

[7]. Corvaglia, V.; Carbajo, D.; Prabhakaran, P.; Ziach, K.; Mandal, P. K.; Santos, V. D.; Legeay, C.; Vogel, R.; Parissi, V.; Pourquier, P.; Huc, I. Carboxylate-functionalized foldamer inhibitors of HIV-1 integrase and Topoisomerase 1: artificial analogues of DNA mimic proteins. Nucleic Acids Res. 2019, 47, 5511-5521.
https://doi.org/10.1093/nar/gkz352

[8]. Paul, M.; Desiraju, G. R. From a binary to a Quaternary cocrystal: An unusual supramolecular synthon. Angew. Chem. Weinheim Bergstr. Ger. 2019, 131, 12155-12159.
https://doi.org/10.1002/ange.201904339

[9]. Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A. "Total synthesis" supramolecular style: Design and hydrogen-bond-directed assembly of ternary supermolecules. Angew. Chem. Int. Ed Engl. 2001, 40, 3240-3242.
https://doi.org/10.1002/1521-3773(20010903)40:17<3240::AID-ANIE3240>3.0.CO;2-X

[10]. PrakashaReddy, J.; Pedireddi, V. R. Synthesis and analysis of some adducts of 3,5-dinitrobenzamide. Tetrahedron 2004, 60, 8817-8827.
https://doi.org/10.1016/j.tet.2004.07.039

[11]. Nangia, A.; Desiraju, G. R. Supramolecular Structures - Reason and Imagination. Acta Crystallogr. A 1998, 54, 934-944.
https://doi.org/10.1107/S0108767398008551

[12]. Stezowski, J. J.; Stigler, R.-D.; Karl, N.; Schuller, K. Charakterisierung eines 1:1 Komplexes von ungewöhnlicher Struktur im binären Phasendiagramm PhenothiazinPhenazin. Z. Kristallogr. 1983, 162 I-314, 213-215. https://doi.org/10.1524/zkri.1983.162.14.i
https://doi.org/10.1524/zkri.1983.162.14.i

[13]. Kennard, O. From data to knowledge-Use of the Cambridge Structural Database for studying molecular interactions. Supramol. Chem. 1993, 1, 277-295.
https://doi.org/10.1080/10610279308035171

[14]. Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

[15]. Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

[16]. Sheldrick, G. M. (1990). SHELXTL. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

[17]. Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thalladi, V. R.; Desiraju, G. R.; Wilson, C. C.; McIntyre, G. J. Crystal engineering and correspondence between molecular and crystal structures. Are 2- and 3-aminophenols anomalous? J. Am. Chem. Soc. 1997, 119, 3477-3480.
https://doi.org/10.1021/ja964254p

[18]. Vijayadas, K. N.; Nair, R. V.; Gawade, R. L.; Kotmale, A. S.; Prabhakaran, P.; Gonnade, R. G.; Puranik, V. G.; Rajamohanan, P. R.; Sanjayan, G. J. Ester vs. amide on folding: a case study with a 2-residue synthetic peptide. Org. Biomol. Chem. 2013, 11, 8348-8356.
https://doi.org/10.1039/c3ob41967c

[19]. Vangala, V. R.; Desiraju, G. R.; Jetti, R. K. R.; Bläser, D.; Boese, R. A 1:1 molecular complex of bis(4-aminophenyl) disulfide and 4-aminothiophenol. Acta Crystallogr. C 2002, 58, o635-6.
https://doi.org/10.1107/S0108270102012994


Supporting information


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

How to cite


Mehmood, T.; Patel, B.; Reddy, J. Eur. J. Chem. 2022, 13(2), 230-233. doi:10.5155/eurjchem.13.2.230-233.2256
Mehmood, T.; Patel, B.; Reddy, J. Phenazine and 10H-phenothiazine cocrystal stabilized by N-H···N and C-H···S hydrogen bonds. Eur. J. Chem. 2022, 13(2), 230-233. doi:10.5155/eurjchem.13.2.230-233.2256
Mehmood, T., Patel, B., & Reddy, J. (2022). Phenazine and 10H-phenothiazine cocrystal stabilized by N-H···N and C-H···S hydrogen bonds. European Journal of Chemistry, 13(2), 230-233. doi:10.5155/eurjchem.13.2.230-233.2256
Mehmood, Tahir, Bhumiben Chandubhai Patel, & Jayarama Prakasha Reddy. "Phenazine and 10H-phenothiazine cocrystal stabilized by N-H···N and C-H···S hydrogen bonds." European Journal of Chemistry [Online], 13.2 (2022): 230-233. Web. 19 Aug. 2022
Mehmood, Tahir, Patel, Bhumiben, AND Reddy, Jayarama. "Phenazine and 10H-phenothiazine cocrystal stabilized by N-H···N and C-H···S hydrogen bonds" European Journal of Chemistry [Online], Volume 13 Number 2 (30 June 2022)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.13.2.230-233.2256

CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | scibey | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2022, 13(2), 230-233 | doi: https://doi.org/10.5155/eurjchem.13.2.230-233.2256 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c) 2022 Authors

Creative Commons License
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).



© Copyright 2010 - 2022  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2022 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.