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Zwitterionic 6-methyl-2-oxo-3-[1-(ureidoiminio)ethyl]-2 H -pyran-4-olate monohydrate
Amel Djedouani, Sihem Boufas, Magali Allain, Gilles Bouet, Mustayeen A.
Khan
To cite this version:
Amel Djedouani, Sihem Boufas, Magali Allain, Gilles Bouet, Mustayeen A. Khan. Zwitterionic 6- methyl-2-oxo-3-[1-(ureidoiminio)ethyl]-2 H -pyran-4-olate monohydrate. Acta Crystallographica Sec- tion E: Structure Reports Online, International Union of Crystallography, 2008, 64 (9), pp.o1785- o1785. �10.1107/S1600536808026032�. �hal-03243903�
electronic reprint
Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
Editors:W. Clegg and D. G. Watson
Zwitterionic
6-methyl-2-oxo-3-[1-(ureidoiminio)ethyl]-2 H -pyran-4-olate monohydrate
Amel Djedouani, Sihem Boufas, Magali Allain, Gilles Bouet and Mustayeen Khan
Acta Cryst.(2008). E64, o1785
This open-access article is distributed under the terms of the Creative Commons Attribution Licence http://creativecommons.org/licenses/by/2.0/uk/legalcode, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Acta Crystallographica Section E
Structure Reports Online
Editors: W. Clegg and D. G. Watson
journals.iucr.org International Union of Crystallography*Chester ISSN 1600-5368
Volume 61 Part 11
November 2005
Inorganic compounds Metal-organic compounds Organic compounds
Acta Crystallographica Section E: Structure Reports Online is the IUCr’s highly popu- lar open-access structural journal. It provides a simple and easily accessible publication mechanism for the growing number of inorganic, metal-organic and organic crystal struc- ture determinations. The electronic submission, validation, refereeing and publication facilities of the journal ensure very rapid and high-quality publication, whilst key indica- tors and validation reports provide measures of structural reliability. In 2007, the journal published over 5000 structures. The average publication time is less than one month.
Crystallography Journals Online is available from journals.iucr.org
Acta Cryst.(2008). E64, o1785 Djedouaniet al. ·C9H11N3O4·H2O
Zwitterionic 6-methyl-2-oxo-3-[1- (ureidoiminio)ethyl]-2 H -pyran-4-olate monohydrate
Amel Djedouani,aSihem Boufas,b* Magali Allain,cGilles Bouetdand Mustayeen Khand
aLaboratoire d’Electrochimie des Mate´riaux Mole´culaires et Complexes, De´partement de Ge´nie des Proce´de´s, Faculte´ des Science de l’Inge´nieur, Universite´ Farhet Abbes de Setif, DZ-19000 Se´tif, Algeria,bUniversite´ 20 Aout 1955, Skikda, Algeria,cCIMM, CNRS UMR 6200, Faculte´ des Science, Angers Cedex, France, anddSONAS, EA 921, Universite´ D’Angers, Faculte´ de Pharmacie, Angers Cedex, France
Correspondence e-mail: [email protected] Received 5 August 2008; accepted 12 August 2008
Key indicators: single-crystal X-ray study;T= 173 K; mean(C–C) = 0.003 A˚;
Rfactor = 0.048;wRfactor = 0.121; data-to-parameter ratio = 14.0.
The title compound, C9H11N3O4H2O, was prepared by the reaction of dehydroacetic acid and semicarbazide hydro- chloride. It crystallizes in a zwitterionic form with cationic iminium and anionic enolate groups. In the crystal structure, the almost planar molecules are held together by N—H O, O—H O and C—H O hydrogen bonds, some of them involving the water molecules.
Related literature
For related literature, see: Taiet al.(2007); Zu-Pei Lianget al.
(2007); Wojciechowskiet al.(2003); Peteket al.(2006); Huang et al.(2006); Bernsteinet al.(1995); Girija & Begum (2004a);
Girijaet al.(2004b); Gowdaet al.(2007)..
Experimental Crystal data C9H11N3O4H2O Mr= 243.22 Monoclinic,P21=c a= 7.1731 (4) A˚ b= 12.6590 (10) A˚ c= 12.3698 (3) A˚ = 104.603 (6)
V= 1086.95 (11) A˚3 Z= 4
MoKradiation = 0.12 mm1 T= 173 (2) K 0.350.050.02 mm
Data collection
Nonius KappaCCD diffractometer Absorption correction: none
11787 measured reflections 2485 independent reflections
1699 reflections withI> 2(I) Rint= 0.055
Refinement
R[F2> 2(F2)] = 0.048 wR(F2) = 0.121 S= 1.03 2485 reflections 178 parameters
H atoms treated by a mixture of independent and constrained refinement
max= 0.33 e A˚3 min=0.26 e A˚3
Table 1
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
N1—H1A O3i 0.84 (2) 2.18 (2) 3.015 (2) 176.3 (17) N1—H1B O1Wii 0.87 (2) 2.30 (2) 3.075 (2) 147.9 (19) N2—H2 O1Wii 0.91 (2) 1.98 (2) 2.839 (2) 158 (2)
N3—H3 O3 0.98 (2) 1.60 (3) 2.476 (2) 147 (2)
O1W—H11W O4 0.82 (3) 1.99 (3) 2.796 (2) 171 (3) O1W—H21W O1iii 0.82 (3) 2.00 (3) 2.823 (2) 178.0 (18)
C3—H3B O1 0.96 2.29 2.812 (3) 114
C7—H7 O4iv 0.93 2.49 3.294 (2) 145
Symmetry codes: (i)xþ1;y12;zþ12; (ii)x;y12;zþ12; (iii)xþ2;y;zþ1;
(iv)xþ1;yþ12;zþ12.
Data collection: COLLECT (Nonius, 1997); cell refinement:
SCALEPACK (Otwinowski & Minor, 1997); data reduction:
DENZO (Otwinowski & Minor, 1997) and SCALEPACK;
program(s) used to solve structure: SHELXS97(Sheldrick, 2008);
program(s) used to refine structure:SHELXL97(Sheldrick, 2008);
molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury(Macraeet al., 2006); software used to prepare material for publication:WinGX(Farrugia, 1999) andPARST(Nardelli, 1995).
This work was supported by Universite´ Farhet Abbes de Se´tif, Se´tif, Algeria.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WK2091).
References
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995).Angew. Chem.
Int. Ed. Engl.34, 1555–1573.
Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.
Farrugia, L. J. (1999).J. Appl. Cryst.32, 837–838.
Girija, C. R. & Begum, N. S. (2004a).Acta Cryst.E60, o535–o536.
Girija, C. R., Begum, N. S., Sridhar, M. A., Lokanath, N. K. & Prasad, J. S.
(2004b).Acta Cryst.E60, o586–o588.
Gowda, B. T., Foro, S. & Fuess, H. (2007).Acta Cryst.E63, o3087.
Huang, L., Chen, D.-B., Qiu, D. & Zhao, B. (2006).Acta Cryst.E62, o5239–
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Nonius (1997).COLLECT. Nonius BV, Delft The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M.
Sweet, pp. 307–326. New York: Academic Press.
Petek, H., Albayrak, C¸ ., Ag˘ar, E. & Kalkan, H. (2006).Acta Cryst.E62, o3685–
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organic compounds
Acta Cryst.(2008). E64, o1785 doi:10.1107/S1600536808026032 Djedouaniet al. o1785
Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
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