2,2-Dibenzyl­hydrazin-1-ium chloride

Tayamon, S.; Ravoof, T.B.S.A.; Tahir, M.I.M.; Crouse, K.A.; Tiekink, E.R.T.

doi:10.1107/S1600536813003966

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 (C-C) = 0.003 Å
R = 0.047
wR = 0.129
Data-to-parameter ratio = 14.5
Details

2,2-Dibenzylhydrazin-1-ium chloride

Shahedeh Tayamon,^a Thahira Begum S. A. Ravoof,^a Mohamed Ibrahim Mohamed Tahir,^a Karen A. Crouse ^a ⁺ and Edward R. T. Tiekink ^b ^*

^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-HCl hydrogen bonds, which lead to a supramolecular undulating ribbon along the a axis comprising edge-shared eight-membered {HNHCl}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); Tayamon et al. (2012). For the synthesis, see: Tarafder et al. (2000). For the structure of the diphenyl analogue of the cation, see: Stender et al. (2003).

Experimental

Crystal data

C₁₄H₁₇N₂⁺·Cl^-
M_r = 248.75
Triclinic, $[P \overline 1]$
a = 5.6155 (4) Å
b = 9.9804 (7) Å
c = 11.7302 (9) Å
= 79.532 (6)°
= 78.508 (6)°
= 83.550 (6)°
V = 631.54 (8) Å³
Z = 2
Cu K radiation
= 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) T_min = 0.72, T_max = 0.95
6961 measured reflections
2407 independent reflections
2076 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(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
_max = 0.45 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
N2-H1NCl1	0.94 (3)	2.30 (3)	3.2130 (18)	163 (2)
N2-H2NCl1ⁱ	0.97 (2)	2.21 (2)	3.1287 (19)	158 (2)
N2-H3NCl1ⁱⁱ	0.93 (3)	2.20 (3)	3.1235 (18)	172 (2)
C8-H8ACg1ⁱⁱⁱ	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); 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: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stender, M., Olmstead, M. M., Balch, A. L., Rios, D. & Attar, S. (2003). Dalton Trans. pp. 4282-4287.
Tarafder, M. T. A., Ali, M. A., Wee, D. J., Azahari, K., Silong, S. & Crouse, K. A. (2000). Transition Met. Chem. 25, 456-460.
Tayamon, S., Ravoof, T. B. S. A., Tahir, M. I. M., Crouse, K. A. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o1640-o1641.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds