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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 [sigma](C-C) = 0.005 Å
R = 0.076
wR = 0.150
Data-to-parameter ratio = 17.1
Details
Open access

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

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-H...Cl hydrogen bond. In the crystal, the chains are linked via C-H...Cl interactions forming two-dimensional networks lying parallel to (101).

Related literature

For applications of similar ligands, see: Taha et al. (2011a[Taha, Z. A., Ajlouni, A. M., Al-Hassan, K. A., Hijazi, A. K. & Faiq, A. B. (2011a). Spectrochim. Acta Part A, 81, 317-323.],b[Taha, Z. A., Ajlouni, A. M., Al Momani, W. & Al-Ghzawi, A. A. (2011b). Spectrochim. Acta Part A, 81, 570-577.]). For analgous structures, see: Ramazani et al. (2006[Ramazani, A., Dolatyari, L., Morsali, A., Yilmaz, V. T. & Bueyuekguengoer, O. (2006). J. Iran. Chem. Soc., 3, 367-370.]); Cheng et al. (2009[Cheng, K., Zheng, Q., Qian, Y., Shi, L., Zhao, J. & Zhu, H. (2009). Bioorg. Med. Chem. 17, 7861-7871.]); Chen et al. (2011[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.]); Pavel et al. (2007[Pavel, K., Kamenicek, J., Petricek, V., Kurecka, A., Kalinska, B. & Mrozinski, J. (2007). Polyhedron, 26, 535-542.]).

[Scheme 1]

Experimental

Crystal data
  • C20H26N3O2+·Cl-

  • Mr = 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[alpha] radiation

  • [mu] = 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[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.94, Tmax = 0.992

  • 8874 measured reflections

  • 2040 independent reflections

  • 1654 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.076

  • wR(F2) = 0.150

  • S = 1.21

  • 2040 reflections

  • 119 parameters

  • Only H-atom displacement parameters refined

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.88 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...Cl1 0.91 2.22 3.128 (2) 176
O1-H1...N2 0.97 1.70 2.577 (4) 148
C1-H1C...Cl1i 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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); 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.  [ISI] [CrossRef] [ChemPort]
Cheng, K., Zheng, Q., Qian, Y., Shi, L., Zhao, J. & Zhu, H. (2009). Bioorg. Med. Chem. 17, 7861-7871.  [CSD] [CrossRef] [PubMed] [ChemPort]
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [details]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
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.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Taha, Z. A., Ajlouni, A. M., Al-Hassan, K. A., Hijazi, A. K. & Faiq, A. B. (2011a). Spectrochim. Acta Part A, 81, 317-323.  [ChemPort]
Taha, Z. A., Ajlouni, A. M., Al Momani, W. & Al-Ghzawi, A. A. (2011b). Spectrochim. Acta Part A, 81, 570-577.  [ChemPort]


Acta Cryst (2012). E68, o3314  [ doi:10.1107/S1600536812045424 ]

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