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Volume 69 
Part 3 
Page o382  
March 2013  

Received 4 February 2013
Accepted 8 February 2013
Online 16 February 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.129
Data-to-parameter ratio = 14.5
Details
Open access

2,2-Dibenzylhydrazin-1-ium chloride

aDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Malaysia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

In the title salt, C14H17N2+·Cl-, the central N atom is pyramidal (sum of bond angles = 330.9°) and there is a near orthogonal relationship between the benzene rings [dihedral angle = 89.95 (10)°]. The crystal packing features N-H...Cl hydrogen bonds, which lead to a supramolecular undulating ribbon along the a axis comprising edge-shared eight-membered {...HNH...Cl}2 synthons. The chains are connected into layers in the ab plane by C-H...[pi] interactions.

Related literature

For background to the synthesis of S-substituted dithiocarbazates and their metal complexes, see: Ravoof et al. (2010[Ravoof, T. B. S. A., Crouse, K. A., Tahir, M. I. M., How, F. N. F., Rosli, R. & Watkin, D. J. (2010). Transition Met. Chem. 35, 871-876.]); Tayamon et al. (2012[Tayamon, S., Ravoof, T. B. S. A., Tahir, M. I. M., Crouse, K. A. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o1640-o1641.]). For the synthesis, see: Tarafder et al. (2000[Tarafder, M. T. A., Ali, M. A., Wee, D. J., Azahari, K., Silong, S. & Crouse, K. A. (2000). Transition Met. Chem. 25, 456-460.]). For the structure of the diphenyl analogue of the cation, see: Stender et al. (2003[Stender, M., Olmstead, M. M., Balch, A. L., Rios, D. & Attar, S. (2003). Dalton Trans. pp. 4282-4287.]).

[Scheme 1]

Experimental

Crystal data
  • C14H17N2+·Cl-

  • Mr = 248.75

  • Triclinic, [P \overline 1]

  • a = 5.6155 (4) Å

  • b = 9.9804 (7) Å

  • c = 11.7302 (9) Å

  • [alpha] = 79.532 (6)°

  • [beta] = 78.508 (6)°

  • [gamma] = 83.550 (6)°

  • V = 631.54 (8) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 2.49 mm-1

  • T = 100 K

  • 0.14 × 0.09 × 0.02 mm

Data collection
  • Oxford Diffraction Xcalibur Eos Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.72, Tmax = 0.95

  • 6961 measured reflections

  • 2407 independent reflections

  • 2076 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.129

  • S = 1.07

  • 2407 reflections

  • 166 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9-C14 phenyl ring.

D-H...A D-H H...A D...A D-H...A
N2-H1N...Cl1 0.94 (3) 2.30 (3) 3.2130 (18) 163 (2)
N2-H2N...Cl1i 0.97 (2) 2.21 (2) 3.1287 (19) 158 (2)
N2-H3N...Cl1ii 0.93 (3) 2.20 (3) 3.1235 (18) 172 (2)
C8-H8A...Cg1iii 0.99 2.64 3.542 (2) 152
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7036 ).


Acknowledgements

Support for the project came from Universiti Putra Malaysia (UPM) through the purchase of the diffractometer and under their Research University Grant Scheme (RUGS No. 9174000), the Malaysian Ministry of Science, Technology and Innovation (grant No. 09-02-04-0752-EA001) and the Malaysian Fundamental Research Grant Scheme (FRGS No. 01-13-11-986FR). We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ravoof, T. B. S. A., Crouse, K. A., Tahir, M. I. M., How, F. N. F., Rosli, R. & Watkin, D. J. (2010). Transition Met. Chem. 35, 871-876.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stender, M., Olmstead, M. M., Balch, A. L., Rios, D. & Attar, S. (2003). Dalton Trans. pp. 4282-4287.  [CSD] [CrossRef]
Tarafder, M. T. A., Ali, M. A., Wee, D. J., Azahari, K., Silong, S. & Crouse, K. A. (2000). Transition Met. Chem. 25, 456-460.  [ISI] [CrossRef] [ChemPort]
Tayamon, S., Ravoof, T. B. S. A., Tahir, M. I. M., Crouse, K. A. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o1640-o1641.  [CSD] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o382  [ doi:10.1107/S1600536813003966 ]

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