N′-(5-Chloro-2-hy­droxy­benzyl­idene)-4-meth­oxy­benzohydrazide

Tan, Y.

doi:10.1107/S1600536812010707

Volume 68
Part 4
Page o1079
April 2012

Received 10 March 2012
Accepted 11 March 2012
Online 17 March 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.038
wR = 0.105
Data-to-parameter ratio = 9.6
Details

N'-(5-Chloro-2-hydroxybenzylidene)-4-methoxybenzohydrazide

Yao Tan ^a ^*

^aSchool of Chemistry and Environmental Engineering, Chongqing Three Gorges University, Chongqing 404000, People's Republic of China
Correspondence e-mail: tanyao1984@yahoo.cn

The asymmetric unit of the title compound, C₁₅H₁₃ClN₂O₃, contains two independent hydrazone molecules. Each molecule adopts an E configuration with respect to the methylidene unit and forms an intramolecular O-HN hydrogen bond. The principal difference between the two unique molecules is the relative orientation of the two benzene rings, the dihedral angles between them being 4.0 (3) and 65.9 (3)°, respectively. In the crystal, molecules are linked through N-HO hydrogen bonds, forming chains running along the c axis.

Related literature

For similar hydrazone derivatives, see: Li (2012); Zhu et al. (2012); Shen et al. (2012); Liu et al. (2011); Lei (2011).

Experimental

Crystal data

C₁₅H₁₃ClN₂O₃
M_r = 304.72
Monoclinic, P 2₁ /c
a = 17.569 (3) Å
b = 8.367 (2) Å
c = 19.454 (3) Å
= 93.683 (3)°
V = 2853.8 (9) Å³
Z = 8
Mo K radiation
= 0.28 mm^-1
T = 298 K
0.11 × 0.08 × 0.07 mm

Data collection

Bruker SMART CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.970, T_max = 0.981
11127 measured reflections
3752 independent reflections
2545 reflections with I > 2(I)
R_int = 0.031
_max = 22.7°

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.105
S = 1.02
3752 reflections
389 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.15 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H4BO2ⁱ	0.89 (1)	1.98 (1)	2.843 (3)	164 (2)
N2-H2O5	0.89 (1)	2.01 (1)	2.883 (3)	166 (2)
O4-H4N3	0.82	1.82	2.540 (3)	145
O1-H1N1	0.82	1.80	2.526 (3)	146
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5210 ).

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Lei, Y. (2011). Acta Cryst. E67, o162.
Li, X.-Y. (2012). Acta Cryst. E68, o709.
Liu, H., Cai, Y., Wu, J., Li, Z. & Li, G. (2011). Acta Cryst. E67, o2139.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shen, X.-H., Zhu, L.-X., Shao, L.-J. & Zhu, Z.-F. (2012). Acta Cryst. E68, o297.
Zhu, Z.-F., Shao, L.-J. & Shen, X.-H. (2012). Acta Cryst. E68, o559.

organic compounds