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Volume 67 
Part 3 
Page o634  
March 2011  

Received 21 January 2011
Accepted 5 February 2011
Online 16 February 2011

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.027
wR = 0.072
Data-to-parameter ratio = 25.4
Details
Open access

(4-Methoxyphenyl)methanaminium chloride

Riadh Kefi,a Zeller Matthiasb and Cherif Ben Nasra*

aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna, Tunisia, and bYoungstown State University, Department of Chemistry, One University Plaza, Youngstown, Ohio 44555-3663, USA
Correspondence e-mail: cherif_bennasr@yahoo.fr

In the crystal structure of the title salt, C8H12NO+·Cl-, the methoxy group of the cation is co-planar with the phenylene moiety with an r.m.s. deviation from the mean plane of only 0.005 Å. The ammonium N atom deviates from this plane by 1.403 (1) Å. In the crystal, the (4-methoxyphenyl)methanaminium cations and chloride anions are linked by N-H...Cl and C-H...O hydrogen bonds, resulting in an open framework architecture with hydrogen-bonded ammonium groups and chloride anions located in layers parallel to (011), separated by more hydrophobic layers with interdigitating anisole groups.

Related literature

For related compounds, see: Oueslati et al. (2005a[Oueslati, A., Rayes, A., Ben Nasr, C. & Rzaigui, M. (2005a). Z. Kristallogr. New Cryst. Struct. 220, 105-106.]); Ben Gharbia et al. (2008[Ben Gharbia, I., Kefi, R., El Glaoui, M., Jeanneau, E. & Ben Nasr, C. (2008). Acta Cryst. E64, m880.]). For hydrogen-bond networks, see: Oueslati et al. (2005b[Oueslati, A., Rayes, A., Ben Nasr, C. & Rzaigui, M. (2005b). Z. Kristallogr. New Cryst. Struct. 220, 365-366.]); Zaouali et al. (2009[Zaouali, D. Z., Ben Amor, F. & Boughzala, H. (2009). X-ray Struct. Anal. Online, 25, 121-122.]). For graph-set theory, see: Bernstein et al. (1995[Bernstein, J., Davids, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For mesomeric effects in related structures, see: Kefi et al. (2006[Kefi, R., Abid, S., Ben Nasr, C. & Rzaigui, M. (2006). Mater. Res. Bull. 42, 404-409.]); El Glaoui et al. (2009[El Glaoui, M., Kefi, R., Jeanneau, E., Lefebvre, F. & Ben Nasr, C. (2009). Open Crystallogr. J. 2, 1-5.]).

[Scheme 1]

Experimental

Crystal data

  • C8H12NO+·Cl-

  • Mr = 173.64

  • Monoclinic, P 21 /c

  • a = 11.4234 (11) Å

  • b = 8.9384 (9) Å

  • c = 8.9490 (9) Å

  • [beta] = 105.904 (1)°

  • V = 878.78 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.38 mm-1

  • T = 100 K

  • 0.55 × 0.42 × 0.38 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc, Madison (WI), USA.]) Tmin = 0.675, Tmax = 0.746

  • 7028 measured reflections

  • 2593 independent reflections

  • 2411 reflections with I > 2[sigma](I)

  • Rint = 0.015
Refinement

  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.072

  • S = 1.07

  • 2593 reflections

  • 102 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...Cl1i 0.91 2.24 3.1475 (9) 176
N1-H1B...Cl1ii 0.91 2.25 3.1502 (8) 170
N1-H1C...Cl1 0.91 2.27 3.1680 (8) 170
C6-H6...O1iii 0.95 2.58 3.4090 (11) 147
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+2, -y+1, -z; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc, Madison (WI), USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc, Madison (WI), USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2550 ).

Acknowledgements

We would like to acknowledge support by the Secretary of State for Scientific Research and Technology of Tunisia. The diffractometer was funded by the NSF (grant 0087210), the Ohio Board of Regents (grant CAP-491) and YSU.

References

Ben Gharbia, I., Kefi, R., El Glaoui, M., Jeanneau, E. & Ben Nasr, C. (2008). Acta Cryst. E64, m880.  [CSD] [CrossRef] [details]
Bernstein, J., Davids, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc, Madison (WI), USA.
El Glaoui, M., Kefi, R., Jeanneau, E., Lefebvre, F. & Ben Nasr, C. (2009). Open Crystallogr. J. 2, 1-5.  [CSD] [CrossRef] [ChemPort]
Kefi, R., Abid, S., Ben Nasr, C. & Rzaigui, M. (2006). Mater. Res. Bull. 42, 404-409.
Oueslati, A., Rayes, A., Ben Nasr, C. & Rzaigui, M. (2005a). Z. Kristallogr. New Cryst. Struct. 220, 105-106.  [ChemPort]
Oueslati, A., Rayes, A., Ben Nasr, C. & Rzaigui, M. (2005b). Z. Kristallogr. New Cryst. Struct. 220, 365-366.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zaouali, D. Z., Ben Amor, F. & Boughzala, H. (2009). X-ray Struct. Anal. Online, 25, 121-122.

Acta Cryst (2011). E67, o634  [ doi:10.1107/S1600536811004363 ]

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