4-[Bis(4-fluoro­phen­yl)meth­yl]-1-[(2E)-3-phenyl­prop-2-en-1-yl]piperazin-1-ium 3-carb­oxy­propano­ate

Kavitha, C.N.; Yathirajan, H.S.; Narayana, B.; Gerber, T.; van Brecht, B.; Betz, R.

doi:10.1107/S1600536813000706

Volume 69
Part 2
Pages o260-o261
February 2013

Received 9 November 2012
Accepted 8 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R = 0.029
wR = 0.081
Data-to-parameter ratio = 10.4
Details

4-[Bis(4-fluorophenyl)methyl]-1-[(2E)-3-phenylprop-2-en-1-yl]piperazin-1-ium 3-carboxypropanoate

Channappa N. Kavitha,^a Hemmige S. Yathirajan,^a Badiadka Narayana,^b Thomas Gerber,^c Benjamin van Brecht ^c and Richard Betz ^c ^*

^aUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India,^bMangalore University, Department of Studies in Chemistry, Mangalagangotri 574 199, India, and ^cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title salt, C₂₆H₂₇F₂N₂⁺·C₄H₅O₄^-, the piperazine N atom bearing the vinylic substituent is protonated. The piperazine ring adopts a chair conformation. In ther crystal, the succinate monoanions are connected via short O-HO hydrogen bonds between the carboxylic acid and carboxylate groups into undulating chains extending along [001] and the flunarizinium monocations are attached to these chains via N⁺-HO^- hydrogen bonds. C-HO interactions connect these chains into a three-dimensional network. The shortest centroid-centroid distance of 3.7256 (10) Å was found between one of the fluorinated benzene rings and the non-fluorinated phenyl ring in the neighbouring molecule related by a glide plane.

Related literature

For pharmaceutical properties of flunarizine, see: Holmes et al. (1984); Amery (1983) and of piperazine derivatives, see: Brockunier et al. (2004); Bogatcheva et al. (2006); Elliott (2011). For related structures, see: Betz et al. (2011a,b); Dayananda et al. (2012a,b); Fillers & Hawkinson (1982); Vanier & Brisse (1983). For puckering analysis of six-membered rings, see: Cremer & Pople (1975); Boeyens (1978). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₂₆H₂₇F₂N₂⁺·C₄H₅O₄^-
M_r = 522.58
Monoclinic, P c
a = 10.7824 (2) Å
b = 10.6270 (2) Å
c = 11.2364 (2) Å
= 91.678 (1)°
V = 1286.97 (4) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 200 K
0.56 × 0.29 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.947, T_max = 0.985
16870 measured reflections
3619 independent reflections
3524 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.081
S = 1.03
3619 reflections
348 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.25 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H72O1	0.96 (2)	1.73 (2)	2.6795 (16)	174 (2)
O3-H3O1ⁱ	0.84	1.84	2.6564 (16)	162
C4-H4AO4ⁱⁱ	0.99	2.58	3.287 (3)	128
C4-H4BO2ⁱⁱⁱ	0.99	2.39	3.3167 (19)	155
C25-H25O2^iv	0.95	2.53	3.4168 (19)	155
C12-H12Cg^v	0.95	2.81	3.7511 (17)	170
Symmetry codes: (i) $[x, -y+2, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+2, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[x+1, -y+1, z-{\script{1\over 2}}]$ ; (v) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2534 ).

Acknowledgements

CNK thanks the University of Mysore for research facilities and the Principal of Maharani's Science College for Women for permission to do research.

References

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