4-(4-Carboxy­benz­yl)-1-methyl­piperazin-1-ium picrate

Li, H.; Hakim Al-arique, Q.N.M.; Yathirajan, H.S.; Narayana, B.; Ramesha, A.R.

doi:10.1107/S1600536809004474

Volume 65
Part 3
Page o518
March 2009

Received 27 December 2008
Accepted 7 February 2009
Online 13 February 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.040
wR = 0.104
Data-to-parameter ratio = 11.7
Details

4-(4-Carboxybenzyl)-1-methylpiperazin-1-ium picrate

Hongqi Li,^a ^* Q. N. M. Hakim Al-arique,^b H. S. Yathirajan,^b B. Narayana ^c and A. R. Ramesha ^d

^aKey Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, People's Republic of China,^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^dRL Fine Chem, Bangalore 560 064, India
Correspondence e-mail: hongqili@dhu.edu.cn

The title compound, C₁₃H₁₉N₂O₂⁺·C₆H₂N₃O₇^-, is a salt obtained by cocrystallization of 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid and picric acid. The cations adopt an `L-shaped' conformation and are linked into chains along [010] by O-HN hydrogen bonds. The NH group of each piperazinium ring forms a hydrogen bond to the phenolate O atom of a picrate anion, and the picrate anions form face-to-face contacts with an interplanar separation of 3.023 (1) Å.

Related literature

For general background, see: Druker et al. (2001). For related structures, see: Swamy et al. (2007); Bindya et al. (2007); Sarojini et al. (2007); Wang & Jia (2008).

Experimental

Crystal data

C₁₃H₁₉N₂O₂⁺·C₆H₂N₃O₇^-
M_r = 463.41
Triclinic, $[P \overline 1]$
a = 7.3020 (12) Å
b = 9.5993 (16) Å
c = 15.131 (3) Å
= 86.448 (2)°
= 79.145 (2)°
= 79.950 (2)°
V = 1025.2 (3) Å³
Z = 2
Mo K radiation
= 0.12 mm^-1
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) T_min = 0.965, T_max = 0.976
5373 measured reflections
3565 independent reflections
2745 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.104
S = 1.06
3565 reflections
305 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.18 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O8-H8N4ⁱ	0.82	1.79	2.6006 (19)	172
N5-H5AO1ⁱⁱ	0.89 (2)	1.89 (2)	2.734 (2)	156.9 (18)
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2341 ).

Acknowledgements

QNMHA thanks R. L. Fine Chem, Bangalore, for a gift sample of 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid. HSY thanks the University of Mysore for research facilities.

References

Bindya, S., Wong, W.-T., Ashok, M. A., Yathirajan, H. S. & Rathore, R. S. (2007). Acta Cryst. C63, o546-o548.
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Druker, B. J., Sawyers, C. L., Kantarjian, H., Resta, D. J., Reese, S. F., Ford, J. M., Capdeville, R. & Talpaz, M. N. (2001). N. Engl. J. Med. 344, 1038-1042.
Sarojini, B. K., Yathirajan, H. S., Mustafa, K., Sarfraz, H. & Bolte, M. (2007). Acta Cryst. E63, o4477.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Swamy, M. T., Ashok, M. A., Yathirajan, H. S., Narayana, B. & Bolte, M. (2007). Acta Cryst. E63, o4919.
Wang, Z.-L. & Jia, L.-H. (2008). Acta Cryst. E64, o665-o666.

organic compounds