skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Structure elucidation of 3-[1-(6-methoxy-2-naphtyl)ethyl]-6-(2,4-dichlorophenyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine, C 23H 18Cl 2N 4OS from synchrotron X-ray powder diffraction

Abstract

The 3-[1-(6-methoxy-2-naphtyl)ethyl]-6-(2,4-dichlorophenyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine, C 23H 18Cl 2N 4OS compound was synthesized, as a member of the family of novel potential anticancer agents. The structure of the title compound was characterized by IR, 1H-NMR, mass spectroscopy, and elemental analysis, previously. In this study, the crystal structure of this compound has been determined from synchrotron X-ray powder diffraction data. The crystal structure was solved by simulated annealing and the final structure was achieved by Rietveld refinement method using soft restrains on all interatomic bond lengths and angles. This compound crystallizes in space groupP21,Z= 2, with the unit-cell parametersa= 15.55645(11) Å,b= 8.61693(6) Å,c= 8.56702(6) Å,β= 104.3270(4)°, andV= 1112.68(1) Å 3. In the crystal structure, strong C-H∙∙∙πand weak intermolecular hydrogen-bonding interactions link the molecules into a three-dimensional network. The molecules are in a head-to-head arrangement in the unit cell.

Authors:
; ; ; ;
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Sponsoring Org.:
FOREIGN
OSTI Identifier:
1417392
Resource Type:
Journal Article
Journal Name:
Powder Diffraction
Additional Journal Information:
Journal Volume: 32; Journal Issue: 04; Journal ID: ISSN 0885-7156
Publisher:
Cambridge University Press
Country of Publication:
United States
Language:
ENGLISH
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Gündoğdu, Gülsüm, Aytaç, Sevim Peri, Müller, Melanie, Tozkoparan, Birsen, and Kaynak, Filiz Betül. Structure elucidation of 3-[1-(6-methoxy-2-naphtyl)ethyl]-6-(2,4-dichlorophenyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine, C23H18Cl2N4OS from synchrotron X-ray powder diffraction. United States: N. p., 2017. Web. doi:10.1017/S0885715617001099.
Gündoğdu, Gülsüm, Aytaç, Sevim Peri, Müller, Melanie, Tozkoparan, Birsen, & Kaynak, Filiz Betül. Structure elucidation of 3-[1-(6-methoxy-2-naphtyl)ethyl]-6-(2,4-dichlorophenyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine, C23H18Cl2N4OS from synchrotron X-ray powder diffraction. United States. doi:10.1017/S0885715617001099.
Gündoğdu, Gülsüm, Aytaç, Sevim Peri, Müller, Melanie, Tozkoparan, Birsen, and Kaynak, Filiz Betül. Fri . "Structure elucidation of 3-[1-(6-methoxy-2-naphtyl)ethyl]-6-(2,4-dichlorophenyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine, C23H18Cl2N4OS from synchrotron X-ray powder diffraction". United States. doi:10.1017/S0885715617001099.
@article{osti_1417392,
title = {Structure elucidation of 3-[1-(6-methoxy-2-naphtyl)ethyl]-6-(2,4-dichlorophenyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine, C23H18Cl2N4OS from synchrotron X-ray powder diffraction},
author = {Gündoğdu, Gülsüm and Aytaç, Sevim Peri and Müller, Melanie and Tozkoparan, Birsen and Kaynak, Filiz Betül},
abstractNote = {The 3-[1-(6-methoxy-2-naphtyl)ethyl]-6-(2,4-dichlorophenyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine, C23H18Cl2N4OS compound was synthesized, as a member of the family of novel potential anticancer agents. The structure of the title compound was characterized by IR,1H-NMR, mass spectroscopy, and elemental analysis, previously. In this study, the crystal structure of this compound has been determined from synchrotron X-ray powder diffraction data. The crystal structure was solved by simulated annealing and the final structure was achieved by Rietveld refinement method using soft restrains on all interatomic bond lengths and angles. This compound crystallizes in space groupP21,Z= 2, with the unit-cell parametersa= 15.55645(11) Å,b= 8.61693(6) Å,c= 8.56702(6) Å,β= 104.3270(4)°, andV= 1112.68(1) Å3. In the crystal structure, strong C-H∙∙∙πand weak intermolecular hydrogen-bonding interactions link the molecules into a three-dimensional network. The molecules are in a head-to-head arrangement in the unit cell.},
doi = {10.1017/S0885715617001099},
journal = {Powder Diffraction},
issn = {0885-7156},
number = 04,
volume = 32,
place = {United States},
year = {2017},
month = {12}
}

Works referenced in this record:

Aspirin and non-steroidal anti-inflammatory drugs for cancer prevention: an international consensus statement
journal, May 2009


Cancer drug discovery by repurposing: teaching new tricks to old dogs
journal, September 2013

  • Gupta, Subash C.; Sung, Bokyung; Prasad, Sahdeo
  • Trends in Pharmacological Sciences, Vol. 34, Issue 9
  • DOI: 10.1016/j.tips.2013.06.005

DASH : a program for crystal structure determination from powder diffraction data
journal, November 2006

  • David, William I. F.; Shankland, Kenneth; van de Streek, Jacco
  • Journal of Applied Crystallography, Vol. 39, Issue 6
  • DOI: 10.1107/S0021889806042117

Discovery and optimization of potent and selective triazolopyridazine series of c-Met inhibitors
journal, November 2009

  • Boezio, Alessandro A.; Berry, Loren; Albrecht, Brian K.
  • Bioorganic & Medicinal Chemistry Letters, Vol. 19, Issue 22
  • DOI: 10.1016/j.bmcl.2009.09.096

WinGX and ORTEP for Windows : an update
journal, July 2012


A fully automatic program for finding the unit cell from powder data
journal, August 1969


2-(6-Phenyl-7 H -1,2,4-triazolo[3,4- b ][1,3,4]thiadiazin-3-yl)-1,3-benzothiazole
journal, September 2011

  • Abdel-Aziz, Hatem A.; Ng, Seik Weng; Tiekink, Edward R. T.
  • Acta Crystallographica Section E Structure Reports Online, Vol. 67, Issue 10
  • DOI: 10.1107/S1600536811036452

Recent advances in magnetic structure determination by neutron powder diffraction
journal, October 1993


New 5-substituted thiazolo[3,2-b][1,2,4]triazol-6-ones: Synthesis and anticancer evaluation
journal, May 2007

  • Lesyk, Roman; Vladzimirska, Olena; Holota, Serhiy
  • European Journal of Medicinal Chemistry, Vol. 42, Issue 5
  • DOI: 10.1016/j.ejmech.2006.12.006

Single-crystal structure validation with the program PLATON
journal, January 2003


Discovery and Optimization of Triazolopyridazines as Potent and Selective Inhibitors of the c-Met Kinase
journal, May 2008

  • Albrecht, Brian K.; Harmange, Jean-Christophe; Bauer, David
  • Journal of Medicinal Chemistry, Vol. 51, Issue 10
  • DOI: 10.1021/jm800043g

OLEX2 : a complete structure solution, refinement and analysis program
journal, January 2009

  • Dolomanov, Oleg V.; Bourhis, Luc J.; Gildea, Richard J.
  • Journal of Applied Crystallography, Vol. 42, Issue 2
  • DOI: 10.1107/S0021889808042726

Rietveld refinement of Debye–Scherrer synchrotron X-ray data from Al 2 O 3
journal, April 1987

  • Thompson, P.; Cox, D. E.; Hastings, J. B.
  • Journal of Applied Crystallography, Vol. 20, Issue 2
  • DOI: 10.1107/S0021889887087090

Indexing of powder diffraction patterns for low-symmetry lattices by the successive dichotomy method
journal, December 1991


EXPO2013 : a kit of tools for phasing crystal structures from powder data
journal, July 2013

  • Altomare, Angela; Cuocci, Corrado; Giacovazzo, Carmelo
  • Journal of Applied Crystallography, Vol. 46, Issue 4
  • DOI: 10.1107/S0021889813013113

Synthesis and antitumor activity studies of some new fused 1,2,4-triazole derivatives carrying 2,4-dichloro-5-fluorophenyl moiety
journal, December 2009

  • Bhat, K. Subrahmanya; Poojary, Boja; Prasad, D. Jagadeesh
  • European Journal of Medicinal Chemistry, Vol. 44, Issue 12
  • DOI: 10.1016/j.ejmech.2009.09.010

A correction for powder diffraction peak asymmetry due to axial divergence
journal, December 1994

  • Finger, L. W.; Cox, D. E.; Jephcoat, A. P.
  • Journal of Applied Crystallography, Vol. 27, Issue 6
  • DOI: 10.1107/S0021889894004218

New techniques for indexing: N-TREOR in EXPO
journal, August 2000

  • Altomare, Angela; Giacovazzo, Carmelo; Guagliardi, Antonietta
  • Journal of Applied Crystallography, Vol. 33, Issue 4
  • DOI: 10.1107/S0021889800006427

A joint theoretical and experimental structural study of two novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives
journal, April 2010

  • Kaynak, Filiz Betül; Aytaç, Sevim Peri; Tozkoparan, Birsen
  • Structural Chemistry, Vol. 21, Issue 4
  • DOI: 10.1007/s11224-010-9613-y

Avogadro: an advanced semantic chemical editor, visualization, and analysis platform
journal, August 2012

  • Hanwell, Marcus D.; Curtis, Donald E.; Lonie, David C.
  • Journal of Cheminformatics, Vol. 4, Issue 1
  • DOI: 10.1186/1758-2946-4-17

Mercury : visualization and analysis of crystal structures
journal, May 2006

  • Macrae, Clare F.; Edgington, Paul R.; McCabe, Patrick
  • Journal of Applied Crystallography, Vol. 39, Issue 3
  • DOI: 10.1107/S002188980600731X

Monte Carlo indexing with McMaille
journal, September 2004


CRYSTALS enhancements: dealing with hydrogen atoms in refinement
journal, August 2010

  • Cooper, Richard I.; Thompson, Amber L.; Watkin, David J.
  • Journal of Applied Crystallography, Vol. 43, Issue 5
  • DOI: 10.1107/S0021889810025598

Synthesis of 3,6-disubstituted 7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines as novel analgesic/anti-inflammatory compounds
journal, November 2009

  • Aytaç, S. Peri; Tozkoparan, Birsen; Kaynak, F. Betül
  • European Journal of Medicinal Chemistry, Vol. 44, Issue 11
  • DOI: 10.1016/j.ejmech.2009.06.026

An X-ray powder diffraction study of cis -dichloridobis(2-methyl-2 H -tetrazol-5-amine-κ N 4 )platinum(II), a tetrazole-containing analogue of cisplatin
journal, May 2011

  • Ivashkevich, Ludmila S.; Serebryanskaya, Tatyana V.; Lyakhov, Alexander S.
  • Acta Crystallographica Section C Crystal Structure Communications, Vol. 67, Issue 6
  • DOI: 10.1107/S0108270111018063

Novel triazolothiadiazines act as potent anticancer agents in liver cancer cells through Akt and ASK-1 proteins
journal, February 2016

  • Aytaç, Peri S.; Durmaz, Irem; Houston, Douglas R.
  • Bioorganic & Medicinal Chemistry, Vol. 24, Issue 4
  • DOI: 10.1016/j.bmc.2016.01.013

( Z )-7-[2-(4-Bromophenyl)hydrazin-1-ylidene]-6-methyl-3-(pyridin-4-yl)-7 H -1,2,4-triazolo[3,4- b ][1,3,4]thiadiazine
journal, April 2012

  • Fun, Hoong-Kun; Chantrapromma, Suchada; Bhat, Mashooq A.
  • Acta Crystallographica Section E Structure Reports Online, Vol. 68, Issue 5
  • DOI: 10.1107/S1600536812017412