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Volume 69 
Part 2 
Page o258  
February 2013  

Received 21 December 2012
Accepted 9 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 290 K
Mean [sigma](C-C) = 0.005 Å
R = 0.072
wR = 0.181
Data-to-parameter ratio = 14.0
Details
Open access

3-[2-(5-tert-Butyl-1,2-oxazol-3-yl)hydrazinylidene]chroman-2,4-dione

aGroup of Physics & Chemistry, Faculty of Natural Sciences & Mathematics, State University of Tetovo, 1200 Tetovo, Macedonia,bInstitute of Chemistry, Faculty of Natural Sciences and Mathematics, Ss. Cyril and Methodius University, Arhimedova 5, 1000 Skopje, Macedonia,cInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str. build. 9, 1113 Sofia, Bulgaria, and dInstitute of Mineralogy and Crystallography, Bulgarian Academy of Sciences, Acad G. Bonchev Str. build. 107, 1113 Sofia, Bulgaria
Correspondence e-mail: popovski.emil@gmail.com

In the title compound, C16H15N3O4, the dihedral angle between the chromane and isoxazole rings [r.m.s. deviations = 0.042 and 0.007 Å, respectively] is 20.33 (12)°. The molecular geometry is stabilized by an intramolecular N-H...O hydrogen bond. In the crystal, N-H...O hydrogen bonds generate chains along the c-axis direction. The crystal studied was a non-morohedral twin.

Related literature

For general background to the use of coumarin derivatives in organic synthesis and as biologically active compounds see: Adavi et al. (2004[Adavi, H. H., Kusanur, R. A. & Kulkarni, M. V. (2004). J. Indian Chem. Soc. 81, 981-986.]); Shi & Zhou (2011[Shi, Y. & Zhou, C.-H. (2011). Bioorg. Med. Chem. Lett. 21, 956-960.]); Toshihiro et al. (2005[Toshihiro, O., Tadashi, K. & Shinichi, Y. (2005). Curr. Med. Chem. Anticancer Agents, 5, 47-52.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15N3O4

  • Mr = 313.31

  • Monoclinic, P 21 /c

  • a = 13.431 (14) Å

  • b = 9.1803 (9) Å

  • c = 12.638 (4) Å

  • [beta] = 100.49 (8)°

  • V = 1532.3 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 290 K

  • 0.28 × 0.26 × 0.21 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.584, Tmax = 1.000

  • 13050 measured reflections

  • 3010 independent reflections

  • 2148 reflections with I > 2[sigma](I)

  • Rint = 0.085

Refinement
  • R[F2 > 2[sigma](F2)] = 0.072

  • wR(F2) = 0.181

  • S = 1.09

  • 3010 reflections

  • 215 parameters

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

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O2 0.89 (4) 1.86 (4) 2.581 (3) 137 (4)
N2-H2...O9i 0.89 (4) 2.70 (4) 3.249 (4) 121 (3)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2443 ).


Acknowledgements

Thanks are due to Bulgarian National Science Fund of the Ministry of Education, Youth and Science for financial support (grants/contracts DRNF02/1 and DRNF02/13).

References

Adavi, H. H., Kusanur, R. A. & Kulkarni, M. V. (2004). J. Indian Chem. Soc. 81, 981-986.  [ChemPort]
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shi, Y. & Zhou, C.-H. (2011). Bioorg. Med. Chem. Lett. 21, 956-960.
Toshihiro, O., Tadashi, K. & Shinichi, Y. (2005). Curr. Med. Chem. Anticancer Agents, 5, 47-52.  [PubMed]


Acta Cryst (2013). E69, o258  [ doi:10.1107/S1600536813000858 ]

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