Bis{(E)-3-[(2-hy­droxy­benzyl­idene)amino]­prop­yl}ammonium chloride

AlDamen, M.A.; Haddad, S.F.

doi:10.1107/S1600536812045424

Volume 68
Part 12
Page o3314
December 2012

Received 6 September 2012
Accepted 2 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.005 Å
R = 0.076
wR = 0.150
Data-to-parameter ratio = 17.1
Details

Bis{(E)-3-[(2-hydroxybenzylidene)amino]propyl}ammonium chloride

Murad A. AlDamen ^a ^* and Salim F. Haddad ^a

^aDepartment of Chemistry, The University of Jordan, Amman 11942, Jordan
Correspondence e-mail: maldamen@ju.edu.jo

The title salt, C₂₀H₂₆N₃O₂⁺·Cl^-, lies across a twofold crystallographic axis with the central N atom of the cation and the chloride anion sitting on this axis, Z' = 0.5. There is an intramolecular hydrogen bond between the hydroxy H atom and the imino N atom. The chloride anion and the cation are connected into chains along the a axis by an N-HCl hydrogen bond. In the crystal, the chains are linked via C-HCl interactions forming two-dimensional networks lying parallel to (101).

Related literature

For applications of similar ligands, see: Taha et al. (2011a,b). For analgous structures, see: Ramazani et al. (2006); Cheng et al. (2009); Chen et al. (2011); Pavel et al. (2007).

Experimental

Crystal data

C₂₀H₂₆N₃O₂⁺·Cl^-
M_r = 375.88
Orthorhombic, P c c n
a = 4.9848 (3) Å
b = 38.714 (2) Å
c = 10.3299 (7) Å
V = 1993.5 (2) Å³
Z = 4
Mo K radiation
= 0.21 mm^-1
T = 100 K
0.52 × 0.37 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Gemini ultra) diffractometer
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ), based on expressions derived from Clark & Reid (1995)] T_min = 0.94, T_max = 0.992
8874 measured reflections
2040 independent reflections
1654 reflections with I > 2(I)
R_int = 0.049

Refinement

R[F² > 2(F²)] = 0.076
wR(F²) = 0.150
S = 1.21
2040 reflections
119 parameters
Only H-atom displacement parameters refined
_max = 0.39 e Å^-3
_min = -0.88 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1ACl1	0.91	2.22	3.128 (2)	176
O1-H1N2	0.97	1.70	2.577 (4)	148
C1-H1CCl1ⁱ	0.97	2.70	3.642 (4)	164
Symmetry code: (i) $[-x-{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2068 ).

References

Chen, Y., Ge, Y., Zhou, W., Ye, L., Gu, Z., Ma, G., Li, W., Li, H. & Cai, Y. (2011). Inorg. Chem. Commun. 14, 1228-1232.
Cheng, K., Zheng, Q., Qian, Y., Shi, L., Zhao, J. & Zhu, H. (2009). Bioorg. Med. Chem. 17, 7861-7871.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Pavel, K., Kamenicek, J., Petricek, V., Kurecka, A., Kalinska, B. & Mrozinski, J. (2007). Polyhedron, 26, 535-542.
Ramazani, A., Dolatyari, L., Morsali, A., Yilmaz, V. T. & Bueyuekguengoer, O. (2006). J. Iran. Chem. Soc., 3, 367-370.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Taha, Z. A., Ajlouni, A. M., Al-Hassan, K. A., Hijazi, A. K. & Faiq, A. B. (2011a). Spectrochim. Acta Part A, 81, 317-323.
Taha, Z. A., Ajlouni, A. M., Al Momani, W. & Al-Ghzawi, A. A. (2011b). Spectrochim. Acta Part A, 81, 570-577.

organic compounds