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

Jashari, A.; Popovski, E.; Mikhova, B.; Nikolova, R.P.; Shivachev, B.L.

doi:10.1107/S1600536813000858

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 (C-C) = 0.005 Å
R = 0.072
wR = 0.181
Data-to-parameter ratio = 14.0
Details

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

Ahmed Jashari,^a Emil Popovski,^b ^* Bozhana Mikhova,^c Rositsa P. Nikolova ^d and Boris L. Shivachev ^d

^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-HO hydrogen bond. In the crystal, N-HO 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); Shi & Zhou (2011); Toshihiro et al. (2005).

Experimental

Crystal data

C₁₆H₁₅N₃O₄
M_r = 313.31
Monoclinic, P 2₁ /c
a = 13.431 (14) Å
b = 9.1803 (9) Å
c = 12.638 (4) Å
= 100.49 (8)°
V = 1532.3 (17) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.584, T_max = 1.000
13050 measured reflections
3010 independent reflections
2148 reflections with I > 2(I)
R_int = 0.085

Refinement

R[F² > 2(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
_max = 0.23 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O2	0.89 (4)	1.86 (4)	2.581 (3)	137 (4)
N2-H2O9ⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

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.
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.

organic compounds