5-Meth­oxy-2-[(2-morpholinoeth­yl)­iminio­meth­yl]phenolate

Mohd Lair, N.; Mohd Ali, H.; Ng, S.W.

doi:10.1107/S1600536809013786

Volume 65
Part 5
Page o1067
May 2009

Received 12 April 2009
Accepted 13 April 2009
Online 18 April 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.040
wR = 0.122
Data-to-parameter ratio = 16.8
Details

5-Methoxy-2-[(2-morpholinoethyl)iminiomethyl]phenolate

Nooraziah Mohd Lair,^a Hapipah Mohd Ali ^a and Seik Weng Ng ^a ^*

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

Each of the two independent molecules of the title comound, C₁₄H₂₀N₂O₃, exists in the zwitterionic form as the imino N atoms are protonated. The =N-H unit forms an intramolecular hydrogen bond to the negatively charged O atom, and also a weaker intermolecular N-HO bond, the latter resulting in inversion dimers.

Related literature

For the structure of 2-[(2-morpholinoethylimino)methyl]phenol, see: Petek et al. (2005).

Experimental

Crystal data

C₁₄H₂₀N₂O₃
M_r = 264.32
Triclinic, $[P \overline 1]$
a = 10.4022 (2) Å
b = 10.7340 (2) Å
c = 14.3497 (3) Å
= 83.523 (1)°
= 74.810 (1)°
= 60.768 (1)°
V = 1349.13 (5) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.25 × 0.25 × 0.25 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
9402 measured reflections
5948 independent reflections
4990 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.122
S = 1.04
5948 reflections
353 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.31 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1	0.88 (1)	1.96 (1)	2.6489 (15)	133 (2)
N1-H1O1ⁱ	0.88 (1)	2.32 (1)	2.9570 (18)	129 (1)
N3-H3O4	0.89 (1)	2.02 (1)	2.6930 (15)	132 (1)
N3-H3O4ⁱⁱ	0.89 (1)	2.29 (1)	2.9505 (18)	132 (1)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+3, -y, -z-1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2422 ).

Acknowledgements

The authors thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Petek, H., Albayrak, C., Iskeleli, N. O., Agar, E. & Senel, I. (2005). Acta Cryst. E61, o3990-o3991.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2009). publCIF. In preparation.

organic compounds