2-[2-(1H-indol-3-yl)ethyl­iminiomethyl]-4-nitro­phenolate

Ali, H.M.; Mohamed Mustafa, M.I.; Rizal, M.R.; Ng, S.W.

doi:10.1107/S1600536808011185

Volume 64
Part 5
Page o913
May 2008

Received 7 January 2008
Accepted 20 April 2008
Online 26 April 2008

Key indicators
Single-crystal X-ray study
T = 139 K
Mean (C-C) = 0.003 Å
R = 0.049
wR = 0.161
Data-to-parameter ratio = 15.3
Details

2-[2-(1H-indol-3-yl)ethyliminiomethyl]-4-nitrophenolate

Hapipah M. Ali,^a M. I. Mohamed Mustafa,^a M. Razali Rizal ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The title Schiff base, C₁₇H₁₅N₃O₃, exists in the zwitterionic form with the phenol H atom transferred to the imine group. Adjacent zwitterions are linked into a linear chain running along the a axis by an indole-hydroxy N-HO hydrogen bond [3.100 (2) Å].

Related literature

For the structure of the zwitterionic 2-{[3-(indol-3-yl)propenyl]methylammonio}-4-methylphenolate, see: Ali et al. (2007).

Experimental

Crystal data

C₁₇H₁₅N₃O₃
M_r = 309.32
Monoclinic, C 2/c
a = 14.5990 (7) Å
b = 9.5027 (5) Å
c = 21.5373 (10) Å
= 95.712 (2)°
V = 2973.0 (3) Å³
Z = 8
Mo K radiation
= 0.10 mm^-1
T = 139 (2) K
0.51 × 0.30 × 0.19 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
6383 measured reflections
3312 independent reflections
2403 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.161
S = 1.06
3312 reflections
216 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 1.18 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2nO1	0.88 (1)	1.87 (2)	2.602 (2)	139 (2)
N3-H3nO2ⁱ	0.88 (1)	2.36 (2)	3.027 (2)	133 (2)
N3-H3nO3ⁱ	0.88 (1)	2.23 (1)	3.100 (2)	171 (2)
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2090 ).

Acknowledgements

The authors thank the University of Canterbury, New Zealand, for the diffraction measurements, and the Science Fund (12-02-03-2031) and the Fundamental Research Grant Scheme (FP064/2006 A) for supporting this study.

References

Ali, H. M., Emmy Maryati, O. & Ng, S. W. (2007). Acta Cryst. E63, o3458.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2008). publCIF. In preparation.

organic compounds