4-(Diethyl­amino)­salicyl­aldehyde azine

Qiu, J.-B.; Yin, B.-Z.

doi:10.1107/S1600536811013237

Volume 67
Part 5
Page o1092
May 2011

Received 7 April 2011
Accepted 8 April 2011
Online 13 April 2011

Key indicators
Single-crystal X-ray study
T = 290 K
Mean (C-C) = 0.004 Å
R = 0.074
wR = 0.228
Data-to-parameter ratio = 18.8
Details

4-(Diethylamino)salicylaldehyde azine

Jing-Bo Qiu ^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 title compound, C₂₂H₃₀N₄O₂, has a crystallographic inversion center located at the mid-point of the N-N single bond. Apart from the four ethyl C atoms, the non-H atoms are nearly coplanar with a mean deviation of 0.0596 (2) Å. An intramolecular O-HN hydrogen bond occurs. In the crystal, weak intermolecular C-HO hydrogen bonds link the molecules into layers parallel to (100).

Related literature

For the synthesis, see Tang et al. (2009). For a related structure, see Gil et al. (2010). For applications of photochromic aromatic Schiff base molecules as molecular memories and switches, see Sliwa et al. (2005).

Experimental

Crystal data

C₂₂H₃₀N₄O₂
M_r = 382.50
Monoclinic, P 2₁ /c
a = 8.736 (5) Å
b = 7.809 (5) Å
c = 16.122 (10) Å
= 103.57 (2)°
V = 1069.1 (11) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 290 K
0.15 × 0.14 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.988, T_max = 0.991
9903 measured reflections
2431 independent reflections
1227 reflections with I > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.074
wR(F²) = 0.228
S = 1.10
2431 reflections
129 parameters
1 restraint
H-atom parameters constrained
_max = 0.45 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8BO1ⁱ	0.97	2.64	3.481 (5)	145
O1-H1N1	0.85	1.88	2.640 (3)	149
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC and 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: NG5147 ).

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

Gil, M., Ziólek, M., Organero, J. A. & Douhal, A. (2010). J. Phys. Chem. C, 114, 9554-9562.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
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.
Sliwa, M., Letard, S., Malfant, I., Nierlich, M., Lacroix, P. G., Asahi, T., Masuhara, H., Yu, P. & Keitaro, N. K. (2005). Chem. Mater. 17, 4717-4735.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Tang, W., Yu, X. & Tong, A. (2009). J. Org. Chem. 74, 2163-2166.

organic compounds