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Volume 69 
Part 4 
Page o603  
April 2013  

Received 4 March 2013
Accepted 20 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.115
Data-to-parameter ratio = 15.9
Details
Open access

Amicarbazone

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and dDepartment of Chemistry, G. Madegowda Institute of Technology, Bharathinagara 571 422, India
Correspondence e-mail: jjasinski@keene.edu

Three independent molecules comprise the asymmetric unit of the title compound, C10H19N5O2, (systematic name: 4-amino-N-tert-butyl-3-isopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxamide) . In all three molecules, the triazole ring and the carboxamide group are almost coplanar [within 4.0-5.9 (9)°], particularly because of the formation of an intramolecular N-H...O hydrogen bond. On other hand, the orientation of the isopropyl group varies significantly from molecule to molecule. The crystal packing is dominated by N-H...O and N-H...N hydrogen bonds, which connect the molecules into infinite chains along [010].

Related literature

For herbicidal properties of amicarbazone and for its preparation, see: Dayan et al. (2009[Dayan, F. E., Trindade, M. L. B. & Velini, E. D. (2009). Weed Sci. 57, 579-583.]); Diehr (1998[Diehr (1998). US Patent No. US005708184A.]). For related structures, see: Crockett et al. (2004[Crockett, R., Forrester, A. R. & Howie, R. A. (2004). Acta Cryst. E60, o460-o461.]); Dupont et al. (1991[Dupont, L., Englebert, S., Dideberg, O., Pirotte, B. & Delarge, J. (1991). Acta Cryst. C47, 1557-1559.]); Heng et al. (2006[Heng, J., Zhu, H.-J., Tang, Q.-G. & Yan, H.-L. (2006). Acta Cryst. E62, o3111-o3112.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C10H19N5O2

  • Mr = 241.30

  • Triclinic, [P \overline 1]

  • a = 11.0298 (2) Å

  • b = 12.2135 (4) Å

  • c = 14.8542 (4) Å

  • [alpha] = 92.244 (2)°

  • [beta] = 95.7020 (19)°

  • [gamma] = 93.379 (2)°

  • V = 1985.65 (9) Å3

  • Z = 6

  • Cu K[alpha] radiation

  • [mu] = 0.72 mm-1

  • T = 123 K

  • 0.35 × 0.25 × 0.15 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.791, Tmax = 1.000

  • 13380 measured reflections

  • 7959 independent reflections

  • 7592 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.115

  • S = 1.05

  • 7959 reflections

  • 499 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2A-H3N1...O1C 0.904 (19) 2.220 (19) 3.0832 (14) 159.6 (15)
N2A-H3N2...N3B 0.91 (2) 2.40 (2) 3.2251 (15) 150.9 (15)
N2A-H3N2...O2B 0.91 (2) 2.483 (19) 3.2492 (14) 141.7 (15)
N5A-H4AB...O1A 0.88 2.05 2.7770 (14) 140
N2B-H3B2...N3Ci 0.929 (19) 2.233 (19) 3.1619 (15) 179.1 (15)
N2B-H3B1...O1Bii 0.89 (2) 2.27 (2) 3.1356 (15) 163.1 (16)
N5B-H4BB...O1B 0.88 2.04 2.7655 (14) 139
N2C-H3C2...O1A 0.906 (18) 2.171 (18) 2.9455 (15) 143.1 (15)
N2C-H3C1...O2B 0.88 (2) 2.41 (2) 3.0718 (14) 132.8 (16)
N5C-H4CB...O1C 0.88 2.05 2.7721 (13) 139
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+2, -z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2097 ).


Acknowledgements

MK thanks the UOM for research facilities. RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Crockett, R., Forrester, A. R. & Howie, R. A. (2004). Acta Cryst. E60, o460-o461.  [CrossRef] [details]
Dayan, F. E., Trindade, M. L. B. & Velini, E. D. (2009). Weed Sci. 57, 579-583.  [CrossRef] [ChemPort]
Diehr (1998). US Patent No. US005708184A.
Dupont, L., Englebert, S., Dideberg, O., Pirotte, B. & Delarge, J. (1991). Acta Cryst. C47, 1557-1559.  [CrossRef] [details]
Heng, J., Zhu, H.-J., Tang, Q.-G. & Yan, H.-L. (2006). Acta Cryst. E62, o3111-o3112.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o603  [ doi:10.1107/S1600536813007782 ]

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