The title compound {systematic name: ethyl N-[N-(3-phenyl-1H-1,2,4-triazol-5-yl)carbamothio­yl]carbamate}, C12H13N5O2S, exists in the 3-phenyl-5-thio­ureido-1H-1,2,4-triazole tautomeric form stabilized by intra­molecular hydrogen bonding between the endocyclic NH H atom and the thio­ureido S atom. The mol­ecular structure is also stabilized by intra­molecular N—H⋯O=C hydrogen bonds arranged in an S(6) graph-set motif within the carbethoxy­thio­urea moiety. The mean planes of the phenyl and 1,2,4-triazole rings make a dihedral angle of 7.61 (11)°. In the crystal, the mol­ecules form two types of inversion dimers. Inter­molecular hydrogen bonds are arranged in R
               2
               2(6) and R
               2
               2(8) graph-set motifs, together forming a network parallel to (111)

Chui, Wai Keung

Dolzhenko, Anna V.

Dolzhenko, Anton V.

Koh, Lip Lin

Tan, Geok Kheng

English

PubMed

10.1107/S1600536810002369Acta Crystallographica Section E: Structure Reports Online662o425

Dolzhenko, A.V.

Tan, G.K.

Koh, L.L.

Chui, W.K.

ScholarBank@NUS

N-Carbethoxy-N'-(3-phenyl-1H-1,2,4-triazol-5-yl)thiourea

The title compound, C12H13N5O2S, exists in the 3-phenyl-5-thioureido-1H-1,2,4-triazole tautomeric form stabilized by intramolecular hydrogen bonding between the endocyclic NH H atom and the thioureido S atom. The molecular structure is also stabilized by intramolecular N-H...O=C hydrogen bonds arranged in an S(6) graph-set motif within the carbethoxythiourea moiety. The mean planes of the phenyl and 1,2,4-triazole rings make a dihedral angle of 7.61 (11)deg. In the crystal, the molecules form two types of inversion dimers. Intermolecular hydrogen bonds are arranged in R22(6) and R22(8) graph-set motifs, together forming a network parallel to (111)

Dolzhenko, Anton

Tan, G.

Koh, L.

Dolzhenko, A.

Chui, W.

espace@Curtin

electronic reprintActa Crystallographica Section EStructure ReportsOnlineISSN 1600-5368Editors: W.T.A. Harrison, J. Simpson andM. WeilN-Carbethoxy-N ′-(3-phenyl-1H-1,2,4-triazol-5-yl)thioureaAnton V. Dolzhenko, Geok Kheng Tan, Lip Lin Koh, Anna V. Dolzhenkoand Wai Keung ChuiActa Cryst. (2010). E66, o425This open-access article is distributed under the terms of the Creative Commons Attribution Licencehttp://creativecommons.org/licenses/by/2.0/uk/legalcode, which permits unrestricted use, distribution, andreproduction in any medium, provided the original authors and source are cited.Acta Crystallographica Section EStructure ReportsOnlineEditors: W. Clegg and D. G. Watsonjournals.iucr.orgInternational Union of Crystallography * ChesterISSN 1600-5368Volume 61Part 11November 2005Inorganic compoundsMetal-organic compoundsOrganic compoundsActa Crystallographica Section E: Structure Reports Online is the IUCr’s highly popu-lar open-access structural journal. It provides a simple and easily accessible publicationmechanism for the growing number of inorganic, metal-organic and organic crystal struc-ture determinations. The electronic submission, validation, refereeing and publicationfacilities 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 journalpublished over 5000 structures. The average publication time is less than one month.Crystallography Journals Online is available from journals.iucr.orgActa Cryst. (2010). E66, o425 Dolzhenko et al. · C12H13N5O2SN-Carbethoxy-N0-(3-phenyl-1H-1,2,4-triazol-5-yl)thioureaAnton V. Dolzhenko,a* Geok Kheng Tan,b Lip Lin Koh,bAnna V. Dolzhenkoa and Wai Keung ChuiaaDepartment of Pharmacy, Faculty of Science, National University of Singapore,18 Science Drive 4, Singapore 117543, Singapore, and bDepartment of Chemistry,Faculty of Science, National University of Singapore, 3 Science Drive 3, Singapore117543, SingaporeCorrespondence e-mail: phada@nus.edu.sgReceived 4 January 2010; accepted 19 January 2010Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.002 Å;R factor = 0.040; wR factor = 0.102; data-to-parameter ratio = 15.9.The title compound {systematic name: ethyl N-[N-(3-phenyl-1H-1,2,4-triazol-5-yl)carbamothioyl]carbamate}, C12H13N5O2S,exists in the 3-phenyl-5-thioureido-1H-1,2,4-triazole tauto-meric form stabilized by intramolecular hydrogen bondingbetween the endocyclic NH H atom and the thioureido Satom. The molecular structure is also stabilized by intra-molecular N—H  O C hydrogen bonds arranged in an S(6)graph-set motif within the carbethoxythiourea moiety. Themean planes of the phenyl and 1,2,4-triazole rings make adihedral angle of 7.61 (11). In the crystal, the molecules formtwo types of inversion dimers. Intermolecular hydrogen bondsare arranged in R22(6) and R22(8) graph-set motifs, togetherforming a network parallel to (111).Related literatureFor the synthesis, tautomerism and crystal structure studies ofrelated 1,2,4-triazoles, see: Dolzhenko et al. (2007, 2009a,b,c).For the structures of related carbethoxythioureas, see: Huanget al. (2009); Lin et al. (2004, 2007); Su et al. (2006); Zhang et al.(2003, 2007). For the graph-set analysis of hydrogen bonding,see: Bernstein et al. (1995).ExperimentalCrystal dataC12H13N5O2SMr = 291.33Triclinic, P1a = 5.9929 (3) Åb = 9.4200 (5) Åc = 12.2000 (7) Å = 91.818 (1) = 92.585 (1) = 101.083 (1)V = 674.62 (6) Å3Z = 2Mo K radiation = 0.25 mm1T = 100 K0.56  0.24  0.12 mmData collectionBruker SMART APEX CCDdiffractometerAbsorption correction: multi-scan(SADABS; Sheldrick, 2001)Tmin = 0.873, Tmax = 0.9718943 measured reflections3092 independent reflections2828 reflections with I > 2(I)Rint = 0.028RefinementR[F 2 > 2(F 2)] = 0.040wR(F 2) = 0.102S = 1.063092 reflections194 parametersH atoms treated by a mixture ofindependent and constrainedrefinementmax = 0.59 e Å3min = 0.20 e Å3Table 1Hydrogen-bond geometry (Å, ).D—H  A D—H H  A D  A D—H  AN5—H5N  S1i 0.81 (2) 2.58 (2) 3.3739 (13) 166.0 (17)N4—H4N  O2 0.84 (2) 1.97 (2) 2.6448 (16) 137.3 (18)N3—H3N  S1 0.84 (2) 2.67 (2) 3.0926 (13) 113.0 (16)N3—H3N  N2ii 0.84 (2) 2.32 (2) 2.9838 (18) 136.5 (18)Symmetry codes: (i) xþ 1;yþ 1;z; (ii) x;yþ 2;z.Data collection: SMART (Bruker, 2001); cell refinement: SAINT(Bruker, 2001); data reduction: SAINT; program(s) used to solvestructure: SHELXS97 (Sheldrick, 2008); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2008); molecular graphics:SHELXTL (Sheldrick, 2008); software used to prepare material forpublication: SHELXTL.This work was supported by the National Medical ResearchCouncil, Singapore (NMRC/NIG/0019/2008).Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: GW2076).ReferencesBernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem.Int. Ed. Engl. 34, 1555–1573.Bruker (2001). SMART and SAINT. Bruker AXS GmbH, Karlsruhe,Germany.Dolzhenko, A. V., Dolzhenko, A. V. & Chui, W. K. (2007). Heterocycles, 71,429–436.Dolzhenko, A. V., Pastorin, G., Dolzhenko, A. V. & Chui, W. K. (2009a).Tetrahedron Lett. 50, 2124–2128.Dolzhenko, A. V., Tan, G. K., Koh, L. L., Dolzhenko, A. V. & Chui, W. K.(2009b). Acta Cryst. E65, o126.Dolzhenko, A. V., Tan, G. K., Koh, L. L., Dolzhenko, A. V. & Chui, W. K.(2009c). Acta Cryst. E65, o125.Huang, B., Kung, P.-P., Rheingold, A. L., DiPasquale, A. & Yanovsky, A.(2009). Acta Cryst. E65, o1249.Lin, Q., Wei, T. B. & Zhang, Y. M. (2007). Phosphorus Sulfur Silicon Relat.Elem. 182, 863–871.Lin, Q., Zhang, Y.-M., Wei, T.-B. & Wang, H. (2004). Acta Cryst. E60, o580–o582.Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Su, B. Q., Liu, G. L., Sheng, L., Wang, X. Q. & Xian, L. (2006). PhosphorusSulfur Silicon Relat. Elem. 181, 745–750.Zhang, Y.-M., Wei, T.-B., Xian, L., Lin, Q. & Yu, K.-B. (2003). Acta Cryst. E59,o905–o906.Zhang, B., Xian, L. & Xiang, X. M. (2007). Z. Kristallogr. New Cryst. Struct.222, 447–448.organic compoundsActa Cryst. (2010). E66, o425 doi:10.1107/S1600536810002369 Dolzhenko et al. o425Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368electronic reprintelectronic reprintelectronic reprintelectronic reprintelectronic reprintelectronic reprintelectronic reprintelectronic reprintelectronic reprintelectronic reprintelectronic reprintelectronic reprint

The title compound {systematic name: ethyl N-[N-(3-phenyl-1H-1,2,4-triazol-5-yl)carbamothioyl]carbamate}, C12H13N5O2S, exists in the 3-phenyl-5-thioureido-1H-1,2,4-triazole tautomeric form stabilized by intramolecular hydrogen bonding between the endocyclic NH H atom and the thioureido S atom. The molecular structure is also stabilized by intramolecular N&amp;#8212;H...O=C hydrogen bonds arranged in an S(6) graph-set motif within the carbethoxythiourea moiety. The mean planes of the phenyl and 1,2,4-triazole rings make a dihedral angle of 7.61&amp;#8197;(11)&amp;#176;. In the crystal, the molecules form two types of inversion dimers. Intermolecular hydrogen bonds are arranged in R22(6) and R22(8) graph-set motifs, together forming a network parallel to (111)

Anton V. Dolzhenko

Geok Kheng Tan

Lip Lin Koh

Anna V. Dolzhenko

Wai Keung Chui

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Acta Crystallographica Section E Structure Reports Online

N-Carbethoxy-N&amp;#8242;-(3-phenyl-1H-1,2,4-triazol-5-yl)thiourea

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/Ueq

organic compounds Acta Cryst.

Phosphorus Sulfur Silicon Relat.

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N-Carbethoxy-N′-(3-phenyl-1H-1,2,4-triazol-5-yl)thiourea

N-Carbethoxy-N′-(3-phenyl-1H-1,2,4-triazol-5-yl)thiourea

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