7-Diethyl­amino-2-oxo-2H-chromene-3-carbohydrazide

Zhang, L.-J.; Yin, B.-Z.

doi:10.1107/S1600536811010944

Volume 67
Part 5
Page o1107
May 2011

Received 16 March 2011
Accepted 24 March 2011
Online 13 April 2011

Key indicators
Single-crystal X-ray study
T = 290 K
Mean (C-C) = 0.002 Å
R = 0.045
wR = 0.117
Data-to-parameter ratio = 16.2
Details

7-Diethylamino-2-oxo-2H-chromene-3-carbohydrazide

Li-Jun Zhang ^a and Bing-Zhu Yin ^a ^*

^aKey Laboratory of Natural Resources of Changbai Mountain, & Functional Molecules (Yanbian University), Ministry of Eduction, Yanji 133002, People's Republic of China
Correspondence e-mail: zqcong@ybu.edu.cn

The asymmetric unit of the title compound, C₁₄H₁₇N₃O₃, contains two independent molecules with different conformations of the ethyl groups. In the crystal, intermolecular N-HO hydrogen bonds link the molecules into ribbons extending along the a axis.

Related literature

For the bioactivity and chemiluminescence of coumarin derivatives, see: Munasinghe et al. (2007). For a related structure, see: Yu et al. (2009). For details of the synthesis, see: Ma et al. (2010).

Experimental

Crystal data

C₁₄H₁₇N₃O₃
M_r = 275.31
Triclinic, $[P \overline 1]$
a = 9.3438 (19) Å
b = 12.771 (3) Å
c = 12.978 (3) Å
= 95.17 (3)°
= 110.13 (3)°
= 106.18 (3)°
V = 1366.4 (5) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 290 K
0.14 × 0.12 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.987, T_max = 0.990
13506 measured reflections
6186 independent reflections
3402 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.117
S = 1.01
6186 reflections
383 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.18 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O2	0.86 (3)	2.01 (2)	2.7098 (18)	137 (2)
N5-H5O5	0.87 (3)	2.03 (2)	2.733 (2)	138 (2)
N6-H6BO3	0.86 (3)	2.30 (1)	3.131 (2)	164 (2)
N3-H3AO3ⁱ	0.87 (3)	2.20 (1)	3.002 (2)	155 (2)
N3-H3BO6ⁱⁱ	0.87 (3)	2.23 (1)	3.039 (2)	154 (2)
Symmetry codes: (i) -x, -y+1, -z+3; (ii) -x+1, -y+1, -z+3.

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5061 ).

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 21062022) and the Open Project of the State Key Laboratory of Supramolecular Structure and Materials, Jilin University.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Ma, W. H., Xu, Q., Du, J. J., Song, B., Peng, X. J., Wang, Z., Li, G. D. & Wang, X. F. (2010). Spectrochim. Acta Part A, 76, 248-252.
Munasinghe, V. R. N., Corrie, J. E. T., Geoff, K. G. & Martin, S. R. (2007). Bioconjugate Chem. 18, 231-237.
Rigaku Corporation (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC & Rigaku Corporation (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yu, T. Z., Zhang, P., Zhao, Y. L., Zhang, H., Meng, J. & Fan, D. W. (2009). Org. Electron. 10, 653-660.

organic compounds