1-(2-Ammonio­eth­yl)piperazin-1,4-diium dihydrogeno­phosphate monohydrogeno­phosphate

Mrad, M.L.; Ferretti, V.; Rzaigui, M.; Ben Nasr, C.

doi:10.1107/S160053681204189X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3120

doi:10.1107/S160053681204189X

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1-(2-Ammonioethyl)piperazin-1,4-diium dihydrogenophosphate monohydrogenophosphate

Mohamed Lahbib Mrad,^a Valeria Ferretti,^b Mohamed Rzaigui ^a and Cherif Ben Nasr ^a ^*

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna, Tunisie, and ^bChemistry Department and Centro di Strutturistica Diffrattometrica, University of Ferrara, Via L Borsari 46, I-44121 Ferrara, Italy.
^*Correspondence e-mail: cherif_bennasr@yahoo.fr

(Received 25 September 2012; accepted 6 October 2012; online 13 October 2012)

The structure of the title compound, C₆H₁₈N₃·HPO₄·H₂PO₄, is characterized by two kinds of inorganic chains running along the a-axis direction. The first one is composed of HPO₄²⁻ anions, while the second one is built up by H₂PO₄⁻ anions. Both types of chains are held together by O—H⋯O hydrogen bonds. The organic cations are attached to these chains through N—H⋯O and C—H⋯O hydrogen bonds. The piperazin-1,4-diium ring adopts a chair conformation.

Related literature

For graph-set motifs, see: Bernstein et al. (1995 ). For reference structural data, see: Kaabi et al. (2004 ); Chtioui & Jouini (2006 ); Jensen et al. (2007 ).

Experimental

Crystal data

C₆H₁₈N₃·HPO₄·H₂PO₄
M_r = 325.20
Monoclinic, P 2₁ /c
a = 12.9417 (2) Å
b = 11.1054 (2) Å
c = 9.3981 (4) Å
β = 92.566 (1)°
V = 1349.37 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 295 K
0.52 × 0.49 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
6163 measured reflections
3518 independent reflections
3167 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.101
S = 1.07
3518 reflections
256 parameters
All H-atom parameters refined
Δρ_max = 0.87 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.93 (2)	1.66 (2)	2.582 (2)	168 (2)
N2—H2na⋯O6	0.91 (2)	1.80 (2)	2.692 (2)	167 (2)
N3—H3na⋯O3	0.87 (3)	1.90 (3)	2.759 (2)	168 (3)
O4—H4o⋯O2ⁱ	0.81 (4)	1.78 (4)	2.582 (2)	170 (3)
N2—H2NB⋯O1ⁱ	0.93 (3)	1.72 (3)	2.656 (2)	175 (3)
N3—H3NB⋯O2ⁱⁱ	0.92 (3)	1.79 (3)	2.683 (2)	164 (2)
N3—H3NC⋯O1ⁱⁱⁱ	0.93 (3)	1.83 (3)	2.747 (2)	171 (2)
O8—H8O⋯O6^iv	0.82 (4)	1.80 (4)	2.614 (2)	173 (4)
O7—H7O⋯O5^v	0.80 (4)	1.74 (4)	2.502 (2)	159 (4)
C3—H3A⋯O1	0.96 (2)	2.58 (2)	3.427 (2)	147 (2)
C5—H5B⋯O5^vi	0.99 (2)	2.44 (2)	3.236 (2)	137 (2)
C2—H2B⋯O4^vii	0.96 (3)	2.45 (3)	3.345 (2)	154 (2)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x+1, -y, -z-1; (v) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (vi) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (vii) $[-x+2, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Data collection: KappaCCD Server Software (Nonius, 1997 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681204189X/ru2043sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204189X/ru2043Isup2.hkl

checkCIF report

Comment top

During the systematic investigation of interaction between monophosphoric acid with organic molecules, numerous structures of monophosphates with organic cations have been described. Hydrogen bonds take part to the stability and the cohesion of the corresponding compounds. We report in this work the chemical preparation and the structural investigation of a new hydrogenomonophosphate C₆H₁₈N₃HO₄PH₂O₄P. The main feature of the atomic arrangement is the existence of two kinds of infinite chains, located at y = 1/4 and y = 3/4, and crossing the unit cell parallel to the a-direction. The first one is composed of HPO₄^2- groups. The second one is formed by H₂PO₄^- anions and characterized by the association between the neighboring chains via strong O—H···O hydrogen bonds with an R₂²(8) graph set motif (Bernstein et al., 1995) centered at (1/2, 1/2, 0) (Fig. 2). The ammonioethylpiperazinediium cations are anchored onto successive chains through N—H···O and C—H···O hydrogen bonds (Fig. 3). The piperazinediium ring adopts a chair conformation and all the measured main features are similar to intramolecular bond distances and angles usually reported for such ring in hydrogenmonophosphate of organic cations (Jensen et al., 2007). With regards to the geometrical features of the monophosphate anions, we remark the existence of two types of P—O distances. The shorter ones, varying between 1.488 (1) and 1.522 (1) Å, correspond to the oxygen atoms double bonded to the phosphorous atom, while the largest ones, varying between 1.556 (2) and 1.586 (1) Å, are associated with the P—OH single bond. This is in agreement with the literature data for monohydrogenophosphate anion in similar arrangements (e.g. Chtioui & Jouini, 2006; Kaabi et al., 2004).

Related literature top

For graph-set motifs, see: Bernstein et al. (1995). For reference structural data, see: Kaabi et al. (2004); Chtioui & Jouini (2006); Jensen et al. (2007).

Experimental top

Crystals of the title compound were prepared at room temperature by slow addition of a solution of orthophosphoric acid (4 mmol in 30 ml of water) to an alcoholic solution of N-aminoethylpiperazine (2 mmol in 30 ml of ethanol). The acid was added until the alcoholic solution becomes turbid. After filtration, the solution was allowed to slowly evaporate at room temperature over several days leading to formation of transparent prismatic crystals with suitable dimensions for single-crystal structural analysis (yield 50%). The crystals are stable for months under normal conditions of temperature and humidity.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al.,1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A view of the title compound, showing 50% probability displacement ellipsoids and arbitrary spheres for the H atoms.
	Fig. 2. Projection along the c-axis of the inorganic chains in the structure of the title compound. PO₄ is given in the tetrahedral representation. Hydrogen bonds are shown as broken lines.
	Fig. 3. The packing diagram of the compound viewed down the b-axis. PO₄ is given in the tetrahedral representation. Hydrogen bonds are shown as broken lines.

1-(2-Ammonioethyl)piperazin-1,4-diium dihydrogenophosphate monohydrogenophosphate top

Crystal data top

C₆H₁₈N₃·HPO₄·H₂PO₄	F(000) = 688
M_r = 325.20	D_x = 1.601 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.9417 (2) Å	Cell parameters from 6163 reflections
b = 11.1054 (2) Å	θ = 2.0–29.0°
c = 9.3981 (4) Å	µ = 0.36 mm⁻¹
β = 92.566 (1)°	T = 295 K
V = 1349.37 (7) Å³	Plate, pale yellow
Z = 4	0.52 × 0.49 × 0.20 mm

Data collection top

Nonius KappaCCD diffractometer	3167 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.016
Graphite monochromator	θ_max = 29.0°, θ_min = 5.1°
ϕ scans and ω scans	h = −17→17
6163 measured reflections	k = −15→12
3518 independent reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: difference Fourier map
wR(F²) = 0.101	All H-atom parameters refined
S = 1.07	w = 1/[σ²(F_o²) + (0.0441P)² + 0.9354P] where P = (F_o² + 2F_c²)/3
3518 reflections	(Δ/σ)_max = 0.001
256 parameters	Δρ_max = 0.87 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

C₆H₁₈N₃·HPO₄·H₂PO₄	V = 1349.37 (7) Å³
M_r = 325.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.9417 (2) Å	µ = 0.36 mm⁻¹
b = 11.1054 (2) Å	T = 295 K
c = 9.3981 (4) Å	0.52 × 0.49 × 0.20 mm
β = 92.566 (1)°

Data collection top

Nonius KappaCCD diffractometer	3167 reflections with I > 2σ(I)
6163 measured reflections	R_int = 0.016
3518 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.101	All H-atom parameters refined
S = 1.07	Δρ_max = 0.87 e Å⁻³
3518 reflections	Δρ_min = −0.69 e Å⁻³
256 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
P1	0.94393 (3)	0.26513 (3)	0.03610 (4)	0.01932 (11)
P2	0.54421 (3)	−0.17696 (4)	−0.42663 (4)	0.02605 (12)
N1	0.74513 (10)	0.02204 (12)	−0.00827 (14)	0.0225 (3)
N2	0.75588 (12)	0.04193 (13)	−0.31310 (15)	0.0284 (3)
N3	0.87175 (12)	−0.00772 (13)	0.27737 (16)	0.0275 (3)
O1	0.84923 (10)	0.33714 (11)	−0.01467 (13)	0.0314 (3)
O2	0.99197 (11)	0.31318 (11)	0.17482 (12)	0.0322 (3)
O3	0.91834 (10)	0.13172 (10)	0.04589 (13)	0.0298 (3)
O4	1.02998 (10)	0.28122 (12)	−0.07732 (14)	0.0319 (3)
O5	0.58176 (14)	−0.24304 (15)	−0.29656 (16)	0.0517 (4)
O6	0.61467 (9)	−0.07876 (11)	−0.47656 (13)	0.0304 (3)
O7	0.52603 (19)	−0.27294 (18)	−0.54576 (19)	0.0687 (7)
O8	0.43568 (12)	−0.12345 (16)	−0.3960 (2)	0.0548 (5)
C1	0.78068 (14)	−0.08225 (14)	−0.09447 (19)	0.0280 (3)
C2	0.82930 (14)	−0.03456 (16)	−0.22692 (19)	0.0306 (3)
C3	0.71060 (14)	0.13880 (16)	−0.22738 (19)	0.0313 (3)
C4	0.66558 (14)	0.09023 (18)	−0.09418 (19)	0.0323 (4)
C5	0.70292 (13)	−0.01058 (16)	0.13353 (18)	0.0287 (3)
C6	0.77789 (14)	−0.07807 (16)	0.23154 (19)	0.0305 (3)
H1A	0.833 (2)	−0.124 (2)	−0.042 (3)	0.047 (7)*
H2NA	0.7042 (19)	−0.002 (2)	−0.356 (3)	0.040 (6)*
H4O	1.011 (3)	0.250 (3)	−0.152 (4)	0.068 (9)*
H1B	0.7218 (18)	−0.130 (2)	−0.118 (2)	0.035 (6)*
H3NA	0.895 (2)	0.033 (2)	0.207 (3)	0.050 (7)*
H3NB	0.921 (2)	−0.062 (2)	0.309 (3)	0.045 (7)*
H3NC	0.8586 (19)	0.045 (2)	0.351 (3)	0.043 (6)*
H2NB	0.790 (2)	0.080 (2)	−0.386 (3)	0.052 (7)*
H2A	0.8872 (18)	0.015 (2)	−0.204 (2)	0.036 (6)*
H2B	0.8482 (19)	−0.099 (2)	−0.288 (3)	0.048 (7)*
H3A	0.7650 (19)	0.195 (2)	−0.203 (3)	0.041 (6)*
H3B	0.6571 (18)	0.177 (2)	−0.284 (3)	0.037 (6)*
H4A	0.6092 (19)	0.037 (2)	−0.114 (3)	0.040 (6)*
H5A	0.6835 (18)	0.066 (2)	0.181 (3)	0.039 (6)*
H6A	0.7415 (19)	−0.098 (2)	0.314 (3)	0.043 (6)*
H6B	0.803 (2)	−0.153 (2)	0.184 (3)	0.048 (7)*
H5B	0.6421 (16)	−0.0630 (19)	0.117 (2)	0.030 (5)*
H4B	0.6433 (19)	0.154 (2)	−0.038 (3)	0.045 (7)*
H8O	0.425 (3)	−0.058 (3)	−0.435 (4)	0.082 (11)*
H7O	0.539 (3)	−0.250 (3)	−0.623 (5)	0.089 (12)*
H1N	0.8034 (18)	0.071 (2)	0.006 (2)	0.038 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.02330 (19)	0.01977 (18)	0.01494 (17)	−0.00404 (13)	0.00127 (13)	−0.00001 (12)
P2	0.0326 (2)	0.0265 (2)	0.0191 (2)	−0.00124 (15)	0.00252 (15)	0.00181 (14)
N1	0.0219 (6)	0.0237 (6)	0.0220 (6)	−0.0004 (5)	0.0016 (5)	−0.0002 (5)
N2	0.0319 (7)	0.0325 (7)	0.0209 (6)	−0.0090 (6)	0.0004 (5)	−0.0021 (5)
N3	0.0332 (7)	0.0263 (6)	0.0226 (6)	0.0012 (5)	−0.0019 (5)	0.0025 (5)
O1	0.0348 (6)	0.0338 (6)	0.0255 (6)	0.0089 (5)	0.0004 (5)	−0.0002 (5)
O2	0.0455 (7)	0.0336 (6)	0.0170 (5)	−0.0129 (5)	−0.0029 (5)	−0.0019 (4)
O3	0.0348 (6)	0.0224 (5)	0.0316 (6)	−0.0089 (4)	−0.0036 (5)	0.0040 (4)
O4	0.0289 (6)	0.0444 (7)	0.0228 (6)	−0.0119 (5)	0.0065 (5)	−0.0030 (5)
O5	0.0701 (10)	0.0554 (9)	0.0303 (7)	0.0276 (8)	0.0105 (7)	0.0157 (6)
O6	0.0274 (6)	0.0297 (6)	0.0339 (6)	−0.0049 (5)	−0.0014 (5)	−0.0016 (5)
O7	0.1099 (16)	0.0634 (11)	0.0350 (8)	−0.0542 (11)	0.0256 (9)	−0.0179 (8)
O8	0.0350 (7)	0.0520 (9)	0.0790 (12)	0.0093 (7)	0.0197 (7)	0.0335 (9)
C1	0.0311 (8)	0.0220 (7)	0.0310 (8)	0.0022 (6)	0.0035 (6)	−0.0020 (6)
C2	0.0292 (8)	0.0323 (8)	0.0309 (8)	0.0018 (6)	0.0067 (6)	−0.0057 (7)
C3	0.0359 (9)	0.0280 (8)	0.0293 (8)	0.0033 (7)	−0.0058 (7)	0.0012 (6)
C4	0.0275 (8)	0.0388 (9)	0.0306 (8)	0.0105 (7)	0.0010 (6)	−0.0004 (7)
C5	0.0277 (7)	0.0330 (8)	0.0259 (8)	−0.0015 (6)	0.0066 (6)	0.0005 (6)
C6	0.0372 (9)	0.0290 (8)	0.0255 (8)	−0.0050 (7)	0.0027 (6)	0.0048 (6)

Geometric parameters (Å, º) top

P1—O2	1.5160 (12)	N3—H3NC	0.93 (3)
P1—O3	1.5218 (11)	O4—H4O	0.81 (3)
P1—O1	1.5222 (12)	O7—H7O	0.80 (4)
P1—O4	1.5858 (12)	O8—H8O	0.82 (4)
P2—O5	1.4886 (14)	C1—C2	1.515 (2)
P2—O6	1.5097 (12)	C1—H1A	0.94 (3)
P2—O8	1.5635 (16)	C1—H1B	0.95 (2)
P2—O7	1.5561 (17)	C2—H2A	0.95 (2)
N1—C4	1.487 (2)	C2—H2B	0.96 (3)
N1—C1	1.498 (2)	C3—C4	1.504 (3)
N1—C5	1.507 (2)	C3—H3A	0.96 (3)
N1—H1N	0.93 (2)	C3—H3B	0.95 (2)
N2—C3	1.481 (2)	C4—H4A	0.96 (2)
N2—C2	1.487 (2)	C4—H4B	0.94 (3)
N2—H2NA	0.91 (3)	C5—C6	1.507 (2)
N2—H2NB	0.93 (3)	C5—H5A	0.99 (2)
N3—C6	1.492 (2)	C5—H5B	0.99 (2)
N3—H3NA	0.87 (3)	C6—H6A	0.95 (3)
N3—H3NB	0.92 (3)	C6—H6B	1.01 (3)

O2—P1—O3	111.88 (7)	C2—C1—H1A	107.2 (16)
O2—P1—O1	112.21 (7)	N1—C1—H1B	107.5 (14)
O3—P1—O1	110.86 (7)	C2—C1—H1B	111.2 (14)
O2—P1—O4	105.37 (7)	H1A—C1—H1B	113 (2)
O3—P1—O4	108.16 (7)	N2—C2—C1	111.62 (14)
O1—P1—O4	108.06 (7)	N2—C2—H2A	105.7 (14)
O5—P2—O6	115.58 (10)	C1—C2—H2A	111.8 (14)
O5—P2—O8	107.41 (9)	N2—C2—H2B	105.8 (15)
O6—P2—O8	110.04 (8)	C1—C2—H2B	111.1 (16)
O5—P2—O7	106.64 (12)	H2A—C2—H2B	111 (2)
O6—P2—O7	110.19 (8)	N2—C3—C4	111.70 (14)
O8—P2—O7	106.54 (13)	N2—C3—H3A	107.2 (15)
C4—N1—C1	108.79 (13)	C4—C3—H3A	110.2 (15)
C4—N1—C5	109.46 (13)	N2—C3—H3B	108.0 (14)
C1—N1—C5	115.14 (12)	C4—C3—H3B	109.1 (15)
C4—N1—H1N	108.7 (14)	H3A—C3—H3B	111 (2)
C1—N1—H1N	105.1 (14)	N1—C4—C3	110.49 (14)
C5—N1—H1N	109.5 (15)	N1—C4—H4A	107.1 (14)
C3—N2—C2	112.18 (13)	C3—C4—H4A	112.3 (15)
C3—N2—H2NA	109.3 (15)	N1—C4—H4B	107.4 (16)
C2—N2—H2NA	111.8 (15)	C3—C4—H4B	109.9 (16)
C3—N2—H2NB	106.3 (17)	H4A—C4—H4B	109 (2)
C2—N2—H2NB	110.2 (16)	N1—C5—C6	114.28 (14)
H2NA—N2—H2NB	107 (2)	N1—C5—H5A	107.5 (14)
C6—N3—H3NA	111.2 (17)	C6—C5—H5A	108.6 (14)
C6—N3—H3NB	107.3 (16)	N1—C5—H5B	108.5 (13)
H3NA—N3—H3NB	109 (2)	C6—C5—H5B	107.0 (12)
C6—N3—H3NC	111.9 (15)	H5A—C5—H5B	111.0 (19)
H3NA—N3—H3NC	109 (2)	N3—C6—C5	114.18 (14)
H3NB—N3—H3NC	109 (2)	N3—C6—H6A	108.0 (15)
P1—O4—H4O	110 (2)	C5—C6—H6A	106.6 (15)
P2—O7—H7O	114 (3)	N3—C6—H6B	106.4 (15)
P2—O8—H8O	113 (3)	C5—C6—H6B	110.8 (15)
N1—C1—C2	108.85 (13)	H6A—C6—H6B	111 (2)
N1—C1—H1A	109.1 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.93 (2)	1.66 (2)	2.582 (2)	168 (2)
N2—H2na···O6	0.91 (2)	1.80 (2)	2.692 (2)	167 (2)
N3—H3na···O3	0.87 (3)	1.90 (3)	2.759 (2)	168 (3)
O4—H4o···O2ⁱ	0.81 (4)	1.78 (4)	2.582 (2)	170 (3)
N2—H2NB···O1ⁱ	0.93 (3)	1.72 (3)	2.656 (2)	175 (3)
N3—H3NB···O2ⁱⁱ	0.92 (3)	1.79 (3)	2.683 (2)	164 (2)
N3—H3NC···O1ⁱⁱⁱ	0.93 (3)	1.83 (3)	2.747 (2)	171 (2)
O8—H8O···O6^iv	0.82 (4)	1.80 (4)	2.614 (2)	173 (4)
O7—H7O···O5^v	0.80 (4)	1.74 (4)	2.502 (2)	159 (4)
C3—H3A···O1	0.96 (2)	2.58 (2)	3.427 (2)	147 (2)
C5—H5B···O5^vi	0.99 (2)	2.44 (2)	3.236 (2)	137 (2)
C2—H2B···O4^vii	0.96 (3)	2.45 (3)	3.345 (2)	154 (2)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, y−1/2, −z+1/2; (iii) x, −y+1/2, z+1/2; (iv) −x+1, −y, −z−1; (v) x, −y−1/2, z−1/2; (vi) x, −y−1/2, z+1/2; (vii) −x+2, y−1/2, −z−1/2.

Experimental details

Crystal data
Chemical formula	C₆H₁₈N₃·HPO₄·H₂PO₄
M_r	325.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	12.9417 (2), 11.1054 (2), 9.3981 (4)
β (°)	92.566 (1)
V (Å³)	1349.37 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.52 × 0.49 × 0.20

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6163, 3518, 3167
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.101, 1.07
No. of reflections	3518
No. of parameters	256
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.87, −0.69

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SIR97 (Altomare et al.,1999), ORTEPIII (Burnett & Johnson, 1996), SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.93 (2)	1.66 (2)	2.582 (2)	168 (2)
N2—H2na···O6	0.91 (2)	1.80 (2)	2.692 (2)	167 (2)
N3—H3na···O3	0.87 (3)	1.90 (3)	2.759 (2)	168 (3)
O4—H4o···O2ⁱ	0.81 (4)	1.78 (4)	2.582 (2)	170 (3)
N2—H2NB···O1ⁱ	0.93 (3)	1.72 (3)	2.656 (2)	175 (3)
N3—H3NB···O2ⁱⁱ	0.92 (3)	1.79 (3)	2.683 (2)	164 (2)
N3—H3NC···O1ⁱⁱⁱ	0.93 (3)	1.83 (3)	2.747 (2)	171 (2)
O8—H8O···O6^iv	0.82 (4)	1.80 (4)	2.614 (2)	173 (4)
O7—H7O···O5^v	0.80 (4)	1.74 (4)	2.502 (2)	159 (4)
C3—H3A···O1	0.96 (2)	2.58 (2)	3.427 (2)	147 (2)
C5—H5B···O5^vi	0.99 (2)	2.44 (2)	3.236 (2)	137 (2)
C2—H2B···O4^vii	0.96 (3)	2.45 (3)	3.345 (2)	154 (2)

Acknowledgements

We would like to acknowledge the support provided by the Secretary of State for Scientific Research and Technology of Tunisia.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bernstein, J., Davids, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895,Oak Ridge National Laboratory,Oak Ridge, Tennessee, USA. Google Scholar
Chtioui, A. & Jouini, A. (2006). Mater. Res. Bull. 41, 569–575. Web of Science CSD CrossRef CAS Google Scholar
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Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
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Volume 68| Part 11| November 2012| Page o3120

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-(2-Ammonio­eth­yl)piperazin-1,4-diium di­hydrogeno­phosphate mono­hydrogeno­phosphate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-(2-Ammonioethyl)piperazin-1,4-diium dihydrogenophosphate monohydrogenophosphate