(E)-N′-(5-Bromo-2-hy­droxy-3-meth­oxy­benzyl­idene)-1H-indole-3-carbo­hydrazide

Li, X.-Y.

doi:10.1107/S1600536811039195

Volume 67
Part 10
Page o2815
October 2011

Received 19 September 2011
Accepted 24 September 2011
Online 30 September 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.009 Å
R = 0.051
wR = 0.125
Data-to-parameter ratio = 12.1
Details

(E)-N'-(5-Bromo-2-hydroxy-3-methoxybenzylidene)-1H-indole-3-carbohydrazide

Xiao-Yan Li ^a ^*

^aZibo Vocational Institute, Zibo 255314, People's Republic of China
Correspondence e-mail: lixiaoyan_zb@126.com

There are three independent moleculesi n the asymmetric unit of the title compound, C₁₈H₁₆BrN₃O₃, in which the dihedral angles between the indole and benzene rings are 76.9 (2), 4.9 (2), and 70.9 (2)°. All three molecules exist in a trans configuration with respect to the methylidene units. In each molecule, there is one intramolecular O-HN hydrogen bond. In the crystal, N-HO hydrogen bonds occur.

Related literature

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011); Lei (2011); Shalash et al. (2010). For the crystal structures of similar compounds reported recently by the author, see: Li (2011a,b).

Experimental

Crystal data

C₁₈H₁₆BrN₃O₃
M_r = 402.25
Monoclinic, P 2₁ /c
a = 15.023 (3) Å
b = 13.860 (3) Å
c = 24.856 (4) Å
= 102.192 (2)°
V = 5058.8 (17) Å³
Z = 12
Mo K radiation
= 2.46 mm^-1
T = 298 K
0.13 × 0.10 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.740, T_max = 0.847
23383 measured reflections
8466 independent reflections
3662 reflections with I > 2(I)
R_int = 0.089

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.125
S = 0.97
8466 reflections
700 parameters
24 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.37 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3O8ⁱ	0.90 (1)	2.73 (4)	3.453 (8)	138 (5)
N9-H9O2	0.89 (1)	2.16 (2)	3.048 (6)	171 (6)
N6-H6O5ⁱⁱ	0.90 (1)	2.28 (2)	3.159 (6)	165 (5)
N2-H2O9ⁱⁱⁱ	0.90 (1)	2.01 (2)	2.893 (6)	168 (6)
N5-H5O6^iv	0.90 (1)	1.99 (1)	2.885 (6)	174 (5)
N8-H8O3^v	0.90 (1)	1.89 (1)	2.795 (6)	179 (6)
O7-H7N7	0.82	1.90	2.615 (6)	146
O4-H4N4	0.82	1.92	2.634 (6)	145
O1-H1N1	0.82	1.91	2.610 (6)	143
Symmetry codes: (i) x, y+1, z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x, -y+1, -z+1; (v) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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: QM2030 ).

Acknowledgements

The author is grateful to the Zibo Vocational Institute for supporting this work.

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Hashemian, S., Ghaeinee, V. & Notash, B. (2011). Acta Cryst. E67, o171.
Lei, Y. (2011). Acta Cryst. E67, o162.
Li, X.-Y. (2011a). Acta Cryst. E67, o1798.
Li, X.-Y. (2011b). Acta Cryst. E67, o2511.
Shalash, M., Salhin, A., Adnan, R., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o3126-o3127.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds