1-Diphenyl­methyl-4-[3-(4-fluoro­benzo­yl)prop­yl]piperazine-1,4-diium dichloride monohydrate

Jing Wang; Yongli Wang; Caiqin Yang

doi:10.1107/S1600536811037378

. 2011 Sep 30;67(Pt 10):o2719. doi: 10.1107/S1600536811037378

1-Diphenylmethyl-4-[3-(4-fluorobenzoyl)propyl]piperazine-1,4-diium dichloride monohydrate

Jing Wang ^a,^*, Yongli Wang ^a, Caiqin Yang ^a

PMCID: PMC3201513 PMID: 22058796

Abstract

In the title compound, C₂₇H₃₁FN₂O²⁺·2Cl⁻·H₂O, the piperazine ring adopts a chair conformation and both N atoms are protonated. The Cl⁻ anions form strong hydrogen bonds to these protons. O/N—H⋯Cl and C—H⋯O hydrogen bonds link the anions, cations and water of hydration into a three-dimensional network.

Related literature

For a related structure, see: Zhou & Jin (1986 ▶). For the synthesis of 1-diphenylmethyl-4-[3-(4-fluorobenzoyl)propyl]piperazine, see: Wang et al. (2003 ▶).

Experimental

Crystal data

C₂₇H₃₁FN₂O²⁺·2Cl⁻·H₂O
M _r = 507.45
Monoclinic,
a = 39.2849 (14) Å
b = 7.3369 (3) Å
c = 19.5158 (7) Å
β = 107.773 (2)°
V = 5356.6 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 298 K
0.37 × 0.21 × 0.11 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.933, T _max = 0.970
19739 measured reflections
4566 independent reflections
3644 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.138
S = 1.03
4566 reflections
313 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: SMART (Siemens, 1994 ▶); cell refinement: SAINT (Siemens, 1994 ▶); 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 Material

Crystal structure: contains datablock(s) global. DOI: 10.1107/S1600536811037378/pv2438sup1.cif

e-67-o2719-sup1.cif^{(24.6KB, cif)}

Supplementary material file. DOI: 10.1107/S1600536811037378/pv2438globalsup2.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1⋯Cl1ⁱ	1.01 (2)	2.24 (2)	3.248 (3)	176 (2)
C6—H6A⋯O1Wⁱⁱ	0.93	2.55	3.397 (4)	152
C14—H14B⋯O1ⁱⁱⁱ	0.97	2.38	3.148 (3)	136
N1—H1A⋯Cl2	0.91	2.09	2.990 (2)	171
O1W—H2⋯Cl2	1.01 (2)	2.20 (2)	3.207 (3)	172 (2)
N2—H2B⋯Cl1	0.91	2.18	3.070 (2)	167

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

We acknowledge financial support for this work by the Hebei Province Natural Science Fund of China (C2006001035), the Science Fund (2009148) of the Education Department and the Science Fund (20090059) of the Health Department of Hebei Province of China.

supplementary crystallographic information

Comment

The crystal structure of 1-diphenylmethyl-4-[3-(4-fluorobenzoyl)propyl]piperazine has been reported (Zhou & Jin, 1986). In this article we report the structure of its dihydrochloride monohydrate.

In the title compound (Fig. 1), the piperazine ring adopts a chair conformation with the piperizine-N atoms protonated. The Cl^- anions form strong halogen hydrogen bonds to these protons. Two chlorine ions and one hydrone bridge piperazine cations through the O—H···Cl and N—H···Cl halogen hydrogen bonds result in a one-dimensional chain structure. Moreover, these hydrogen bonds, as well as C═O···H hydrogen bonds (Table 1), link the molecular moieties into a two dimensional sheet in the b-c plane. The water of hydration further consolidates the structure via hydrogen bonds of the type O—H···C. Overall, the individual molecule packs together into a three-dimensional network with a spiral structure motif (Fig. 2).

Experimental

The 1-diphenylmethyl-4-[3-(4-fluorobenzoyl)propyl]piperazine base was synthesized according to a reported procedure (Wang et al., 2003). The title compound was prepared by passing dry hydrochloride gas (100 mg) through a solution of 200 mg base in ethanol (2 ml). The single-crystals of the title compound suitable for X-ray analysis were obtained by vapor diffusion in a solution of chloroform in which the compound was soluble by benzene acting as anti-solvent.