2-[(E)-4-Diethyl­amino-2-hy­droxy­benzyl­idene]hydrazinecarboxamide

Fun, H.-K.; Ooi, C.W.; Malladi, S.; Isloor, A.M.; Shivananda, K.N.

doi:10.1107/S1600536812000311

Volume 68
Part 2
Page o380
February 2012

Received 16 December 2011
Accepted 4 January 2012
Online 14 January 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R = 0.068
wR = 0.220
Data-to-parameter ratio = 12.1
Details

2-[(E)-4-Diethylamino-2-hydroxybenzylidene]hydrazinecarboxamide

Hoong-Kun Fun,^a ^*⁺ Chin Wei Ooi,^a Shridhar Malladi,^b Arun M. Isloor ^b and Kammasandra N. Shivananda ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bMedicinal Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and ^cSchulich Faculty of Chemistry, Technion Israel Institute of Technology, Haifa-Israel
Correspondence e-mail: hkfun@usm.my

Two molecules make up the asymmetric unit of the title compound, C₁₂H₁₈N₄O₂, and both feature an intramolecular O-HN hydrogen bond, which generates an S(6) ring. The diethylamino group of one of the molecules is disordered over two sets of sites in a 0.59 (2):0.41 (2) ratio. In the crystal, N-HO hydrogen bonds link the molecules into sheets lying parallel to the ac plane and C-H [pi] interactions are also observed.

Related literature

For a related structure and background references to semicarbazides and semicarbazones, see: Fun et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For reference bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₂H₁₈N₄O₂
M_r = 250.30
Triclinic, $[P \overline 1]$
a = 8.794 (2) Å
b = 12.532 (3) Å
c = 14.292 (5) Å
= 112.911 (7)°
= 96.033 (7)°
= 107.296 (5)°
V = 1340.8 (7) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.35 × 0.12 × 0.03 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.970, T_max = 0.998
15373 measured reflections
4567 independent reflections
2179 reflections with I > 2(I)
R_int = 0.082

Refinement

R[F² > 2(F²)] = 0.068
wR(F²) = 0.220
S = 1.00
4567 reflections
378 parameters
H-atom parameters constrained
_max = 0.37 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1B-C6B benzene ring.

D-HA	D-H	HA	DA	D-HA
O1A-H1O1N2A	0.87	1.79	2.608 (4)	157
O1B-H2O1N2B	0.87	1.91	2.654 (5)	142
N3A-H1N3O2Aⁱ	0.95	1.90	2.832 (4)	168
N3B-H2N3O2Bⁱⁱ	0.99	1.87	2.837 (4)	168
N4A-H1N4O1B	0.79	2.40	3.077 (5)	144
N4A-H2N4O2Bⁱⁱⁱ	0.90	2.01	2.901 (5)	172
N4B-H3N4O2A^iv	0.78	2.14	2.911 (5)	167
N4B-H4N4O1A	0.89	2.20	2.962 (5)	144
C9A-H9ABCg1^v	0.97	2.83	3.733 (19)	156
C10X-H10FCg1^v	0.96	2.71	3.46 (3)	136
Symmetry codes: (i) -x, -y, -z; (ii) -x+2, -y, -z+1; (iii) x-1, y, z; (iv) x+1, y, z; (v) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6571 ).

Acknowledgements

HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). CWO also thanks the Malaysian Government and USM for the award of the post of research assistant under the Research University Grant (1001/PFIZIK/811151). AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award.

References

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Chia, T. S., Malladi, S., Isloor, A. M. & Shivananda, K. N. (2011). Acta Cryst. E67, o2885-o2886.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds