European Journal of Chemistry

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

Crossmark


Main Article Content

Tahir Mehmood
Bhumiben Chandubhai Patel
Jayarama Prakasha Reddy

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.


icon graph This Abstract was viewed 424 times | icon graph Article PDF downloaded 146 times icon graph Article CIF FILE downloaded 0 times

How to Cite
(1)
Mehmood, T.; Patel, B. C.; Reddy, J. P. Phenazine and 10H-Phenothiazine Cocrystal Stabilized by N-H···N and C-H···S Hydrogen Bonds. Eur. J. Chem. 2022, 13, 230-233.

Article Details

Share
Crossref - Scopus - Google - European PMC
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

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/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 (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).