Piperazine-1,4-diium bis­(2-carb­oxy-1H-pyrazole-4-carboxyl­ate) tetra­hydrate

Zhou, X.-H.

doi:10.1107/S160053681003655X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2578

doi:10.1107/S160053681003655X

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Piperazine-1,4-diium bis(2-carboxy-1H-pyrazole-4-carboxylate) tetrahydrate

Xin-Hui Zhou ^a ^*

^aKey Laboratory for Organic Electronics & Information Displays (KLOEID) and Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications (NUPT), Nanjing 210046, People's Republic of China
^*Correspondence e-mail: iamxhzhou@njupt.edu.cn

(Received 8 September 2010; accepted 13 September 2010; online 18 September 2010)

The asymmetric unit of the title compound, C₄H₁₂N₂²⁺·2C₅H₃N₂O₄⁻·4H₂O, comprises one-half of a piperazine-1,4-diium cation, which lies on an inversion centre, a 2-carboxy-1H-pyrazole-4-carboxylate anion and two water molecules. An extensive network of intermolecular O—H⋯O, N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds between the cations, anions and water molecules leads to a three-dimensional supramolecular framework.

Related literature

For 3,5-pyrazoledicarboxylic acid, see: King et al. (2003 ); Pan et al. (2001 ). For reference structural data, see: Li & Su (2007 ); Reviriego et al. (2006 ).

Experimental

Crystal data

C₄H₁₂N₂·2C₅H₃N₂O₄·4H₂O
M_r = 470.41
Monoclinic, P 2₁ /c
a = 8.3363 (13) Å
b = 16.246 (3) Å
c = 7.3930 (11) Å
β = 90.812 (3)°
V = 1001.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 291 K
0.15 × 0.14 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.980, T_max = 0.984
5265 measured reflections
1946 independent reflections
1524 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.147
S = 1.10
1946 reflections
169 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5ⁱ	0.84 (3)	1.93 (3)	2.746 (3)	167 (3)
O2—H2⋯O4ⁱⁱ	0.87 (3)	1.65 (3)	2.520 (2)	175 (3)
N3—H3A⋯O4	0.88 (3)	2.36 (3)	2.918 (3)	121 (2)
N3—H3A⋯N2	0.88 (3)	2.01 (3)	2.865 (3)	162 (3)
N3—H3B⋯O3ⁱⁱⁱ	0.88 (3)	2.20 (3)	2.999 (3)	150 (3)
O5—H5B⋯O6	0.85 (4)	2.00 (4)	2.831 (3)	166 (3)
O5—H5A⋯O6^iv	0.92 (4)	1.96 (4)	2.833 (3)	157 (3)
O6—H6C⋯O3^v	0.93 (3)	1.85 (3)	2.779 (3)	173 (3)
O6—H6D⋯O3^vi	0.76 (3)	2.14 (3)	2.858 (3)	158 (4)
C6—H6B⋯O5^vii	0.97	2.53	3.348 (4)	142
C7—H7A⋯O1^viii	0.97	2.53	3.091 (3)	117
Symmetry codes: (i) x+1, y, z; (ii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x, -y+1, -z+1; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (vii) -x+1, -y+1, -z; (viii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2008 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681003655X/om2361sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681003655X/om2361Isup2.hkl

checkCIF report

Comment top

Hydrogen bonding, as the strongest and most directional intermolecular force, has been intensively investigated in organic crystalline solids. The ligand, 3,5-pyrazoledicarboxylic acid, known both as a multiple proton donor and acceptor, has six potential hydrogen-bond sites involving both the nitrogen atoms of the pyrazole ring and all of the carboxylate O atoms. and it can form mono-, di- and trianionic ligand species through deprotonation (King et al. 2003; Pan et al. 2001).

We report here the synthesis and structure of piperazine-1,4-diium bis(2-carboxy-1H-pyrazole-4-carboxylate) tetrahydrate, as shown in Fig.1, which was obtained from a solution of 3,5-pyrazoledicarboxylic acid, Cd(NO₃)₂.4H₂O and piperazine. Bond distances and angles are normal (Li & Su, 2007; Reviriego et al. 2006). The asymmetric unit of the title compound comprises one half of the piperazine-1,4-diium cation, which lies about an inversion centre, a 2-carboxy-1H-pyrazole-4-carboxylate anion and two water molecules. In the crystal structure molecules are interlinked by hydrogen bonds (Table 1 and Fig. 2). The 2-carboxy-1H-pyrazole-4-carboxylate anoins are interconnected with each other through the O2—H2···O4ⁱⁱⁱ hydrogen bonds. The 2-carboxy-1H-pyrazole-4-carboxylate anions are connected with the piperazine-1,4-diium cations through the N3—H3A···O4, N3—H3A···N2, N3—H3B···O3^iv and C7—H7A···O1^viii hydrogen bonds to form the three-dimensional supramolecular framework.

Related literature top

For 3,5-pyrazoledicarboxylic acid, see: King et al. (2003); Pan et al. (2001). For reference structural data, see: Li & Su (2007); Reviriego et al. (2006).

Experimental top

A mixture of 3,5-pyrazoledicarboxylic acid (0.2 mmol, 34.8 mg), Cd(NO₃)₂.4H₂O (0.1 mmol, 30.8 mg), piperazine (0.2 mmol, 17.2 mg) and H₂O (8 ml) was sealed in a 15 ml Teflon-lined bomb and heated at 150°C for 5 days. The reaction mixture was slowly cooled to room temperature to obtain the colorless block crystals of (I) suitable for X-ray diffraction analysis.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids. H atoms are shown as small spheres of arbitary radii. [Symmetry code; (i) 1 - x, 1 - y, -z.]
	Fig. 2. A view of the crystal packing. Hydrogen bonds are indicated by green dashed lines.

Piperazine-1,4-diium bis(2-carboxy-1H-pyrazole-4-carboxylate) tetrahydrate top

Crystal data top

C₄H₁₂N₂·2C₅H₃N₂O₄·4H₂O	F(000) = 496
M_r = 470.41	D_x = 1.560 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1373 reflections
a = 8.3363 (13) Å	θ = 2.7–24.0°
b = 16.246 (3) Å	µ = 0.14 mm⁻¹
c = 7.3930 (11) Å	T = 291 K
β = 90.812 (3)°	Block, white
V = 1001.2 (3) Å³	0.15 × 0.14 × 0.12 mm
Z = 2

Data collection top

Bruker SMART APEX CCD diffractometer	1946 independent reflections
Radiation source: fine-focus sealed tube	1524 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
phi and ω scans	θ_max = 26.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
T_min = 0.980, T_max = 0.984	k = −13→19
5265 measured reflections	l = −8→9

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0729P)²] where P = (F_o² + 2F_c²)/3
1946 reflections	(Δ/σ)_max < 0.001
169 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₄H₁₂N₂·2C₅H₃N₂O₄·4H₂O	V = 1001.2 (3) Å³
M_r = 470.41	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.3363 (13) Å	µ = 0.14 mm⁻¹
b = 16.246 (3) Å	T = 291 K
c = 7.3930 (11) Å	0.15 × 0.14 × 0.12 mm
β = 90.812 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	1946 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1524 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.984	R_int = 0.051
5265 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.41 e Å⁻³
1946 reflections	Δρ_min = −0.23 e Å⁻³
169 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
C1	1.1506 (3)	0.78226 (15)	0.2962 (3)	0.0267 (6)
C2	0.9861 (3)	0.77149 (14)	0.2216 (3)	0.0233 (6)
C3	0.8727 (3)	0.82885 (15)	0.1741 (3)	0.0256 (6)
H3	0.8827	0.8858	0.1785	0.031*
C4	0.7391 (3)	0.78344 (14)	0.1178 (3)	0.0226 (5)
C5	0.5785 (3)	0.81182 (15)	0.0528 (3)	0.0246 (6)
C6	0.6653 (4)	0.51108 (17)	−0.0379 (5)	0.0455 (8)
H6A	0.7149	0.4999	0.0790	0.055*
H6B	0.7496	0.5242	−0.1223	0.055*
C7	0.4237 (3)	0.56416 (16)	0.1024 (4)	0.0380 (7)
H7A	0.3509	0.6107	0.1070	0.046*
H7B	0.4666	0.5548	0.2233	0.046*
N1	0.9196 (2)	0.69726 (13)	0.1933 (3)	0.0266 (5)
H1	0.962 (3)	0.6522 (18)	0.220 (4)	0.032*
N2	0.7696 (2)	0.70254 (12)	0.1296 (3)	0.0262 (5)
N3	0.5556 (3)	0.58226 (14)	−0.0224 (3)	0.0399 (7)
H3A	0.604 (4)	0.6268 (19)	0.020 (4)	0.048*
H3B	0.514 (4)	0.5944 (18)	−0.130 (4)	0.048*
O1	1.2097 (2)	0.85001 (11)	0.3144 (3)	0.0454 (6)
O2	1.2193 (2)	0.71272 (11)	0.3390 (3)	0.0360 (5)
H2	1.311 (4)	0.7215 (17)	0.394 (4)	0.043*
O3	0.5431 (2)	0.88609 (10)	0.0779 (3)	0.0360 (5)
O4	0.4901 (2)	0.75870 (11)	−0.0188 (3)	0.0358 (5)
O5	0.0107 (3)	0.53912 (14)	0.2765 (4)	0.0528 (7)
H5A	−0.077 (5)	0.510 (2)	0.316 (5)	0.063*
H5B	0.093 (5)	0.539 (2)	0.346 (5)	0.063*
O6	0.2621 (2)	0.51492 (13)	0.5325 (3)	0.0476 (6)
H6C	0.323 (4)	0.472 (2)	0.486 (5)	0.057*
H6D	0.320 (4)	0.549 (2)	0.556 (5)	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0215 (13)	0.0285 (14)	0.0299 (15)	0.0002 (11)	−0.0059 (11)	0.0006 (11)
C2	0.0199 (12)	0.0226 (13)	0.0272 (14)	−0.0006 (10)	−0.0039 (10)	0.0002 (10)
C3	0.0205 (13)	0.0193 (12)	0.0369 (15)	−0.0020 (9)	−0.0056 (10)	−0.0016 (10)
C4	0.0189 (12)	0.0203 (12)	0.0286 (14)	0.0011 (10)	−0.0045 (10)	−0.0004 (10)
C5	0.0159 (12)	0.0228 (13)	0.0351 (15)	−0.0025 (10)	−0.0040 (10)	0.0030 (11)
C6	0.0399 (17)	0.0443 (18)	0.052 (2)	−0.0078 (14)	0.0024 (14)	−0.0050 (15)
C7	0.0455 (17)	0.0286 (15)	0.0398 (17)	0.0027 (12)	−0.0021 (14)	−0.0035 (12)
N1	0.0191 (11)	0.0186 (11)	0.0417 (14)	0.0025 (9)	−0.0092 (9)	0.0022 (9)
N2	0.0169 (10)	0.0215 (11)	0.0398 (13)	−0.0001 (8)	−0.0103 (9)	0.0011 (9)
N3	0.0616 (17)	0.0210 (12)	0.0370 (15)	−0.0144 (11)	−0.0069 (12)	−0.0007 (10)
O1	0.0326 (11)	0.0284 (11)	0.0745 (16)	−0.0083 (8)	−0.0248 (10)	0.0010 (10)
O2	0.0195 (9)	0.0284 (10)	0.0597 (14)	−0.0004 (8)	−0.0183 (9)	0.0030 (9)
O3	0.0239 (10)	0.0218 (10)	0.0622 (14)	0.0044 (8)	−0.0093 (9)	−0.0002 (9)
O4	0.0221 (9)	0.0282 (10)	0.0566 (13)	−0.0002 (8)	−0.0167 (9)	−0.0048 (9)
O5	0.0395 (12)	0.0361 (12)	0.0826 (19)	0.0042 (10)	−0.0040 (12)	0.0144 (11)
O6	0.0345 (12)	0.0334 (12)	0.0748 (17)	−0.0035 (9)	−0.0015 (11)	−0.0107 (11)

Geometric parameters (Å, º) top

C1—O1	1.213 (3)	C6—H6B	0.9700
C1—O2	1.304 (3)	C7—N3	1.476 (4)
C1—C2	1.481 (3)	C7—C6ⁱ	1.504 (4)
C2—N1	1.342 (3)	C7—H7A	0.9700
C2—C3	1.369 (3)	C7—H7B	0.9700
C3—C4	1.395 (3)	N1—N2	1.333 (3)
C3—H3	0.9300	N1—H1	0.84 (3)
C4—N2	1.341 (3)	N3—H3A	0.88 (3)
C4—C5	1.489 (3)	N3—H3B	0.88 (3)
C5—O4	1.248 (3)	O2—H2	0.87 (3)
C5—O3	1.256 (3)	O5—H5A	0.92 (4)
C6—N3	1.480 (4)	O5—H5B	0.85 (4)
C6—C7ⁱ	1.504 (4)	O6—H6C	0.93 (3)
C6—H6A	0.9700	O6—H6D	0.76 (3)

O1—C1—O2	125.7 (2)	H6A—C6—H6B	108.0
O1—C1—C2	121.4 (2)	N3—C7—C6ⁱ	109.4 (2)
O2—C1—C2	112.9 (2)	N3—C7—H7A	109.8
N1—C2—C3	106.9 (2)	C6ⁱ—C7—H7A	109.8
N1—C2—C1	122.8 (2)	N3—C7—H7B	109.8
C3—C2—C1	130.3 (2)	C6ⁱ—C7—H7B	109.8
C2—C3—C4	105.2 (2)	H7A—C7—H7B	108.2
C2—C3—H3	127.4	N2—N1—C2	112.3 (2)
C4—C3—H3	127.4	N2—N1—H1	122.4 (18)
N2—C4—C3	110.4 (2)	C2—N1—H1	125.1 (19)
N2—C4—C5	119.6 (2)	N1—N2—C4	105.21 (19)
C3—C4—C5	130.0 (2)	C7—N3—C6	111.1 (2)
O4—C5—O3	126.1 (2)	C7—N3—H3A	106 (2)
O4—C5—C4	116.5 (2)	C6—N3—H3A	113 (2)
O3—C5—C4	117.5 (2)	C7—N3—H3B	108 (2)
N3—C6—C7ⁱ	111.0 (2)	C6—N3—H3B	110 (2)
N3—C6—H6A	109.4	H3A—N3—H3B	108 (3)
C7ⁱ—C6—H6A	109.4	C1—O2—H2	110.5 (18)
N3—C6—H6B	109.4	H5A—O5—H5B	117 (3)
C7ⁱ—C6—H6B	109.4	H6C—O6—H6D	107 (3)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱⁱ	0.84 (3)	1.93 (3)	2.746 (3)	167 (3)
O2—H2···O4ⁱⁱⁱ	0.87 (3)	1.65 (3)	2.520 (2)	175 (3)
N3—H3A···O4	0.88 (3)	2.36 (3)	2.918 (3)	121 (2)
N3—H3A···N2	0.88 (3)	2.01 (3)	2.865 (3)	162 (3)
N3—H3B···O3^iv	0.88 (3)	2.20 (3)	2.999 (3)	150 (3)
O5—H5B···O6	0.85 (4)	2.00 (4)	2.831 (3)	166 (3)
O5—H5A···O6^v	0.92 (4)	1.96 (4)	2.833 (3)	157 (3)
O6—H6C···O3^vi	0.93 (3)	1.85 (3)	2.779 (3)	173 (3)
O6—H6D···O3^vii	0.76 (3)	2.14 (3)	2.858 (3)	158 (4)
C6—H6B···O5ⁱ	0.97	2.53	3.348 (4)	142
C7—H7A···O1^viii	0.97	2.53	3.091 (3)	117

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) x+1, −y+3/2, z+1/2; (iv) x, −y+3/2, z−1/2; (v) −x, −y+1, −z+1; (vi) −x+1, y−1/2, −z+1/2; (vii) x, −y+3/2, z+1/2; (viii) x−1, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₄H₁₂N₂·2C₅H₃N₂O₄·4H₂O
M_r	470.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	8.3363 (13), 16.246 (3), 7.3930 (11)
β (°)	90.812 (3)
V (Å³)	1001.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.15 × 0.14 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.980, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	5265, 1946, 1524
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.147, 1.10
No. of reflections	1946
No. of parameters	169
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.23

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.84 (3)	1.93 (3)	2.746 (3)	167 (3)
O2—H2···O4ⁱⁱ	0.87 (3)	1.65 (3)	2.520 (2)	175 (3)
N3—H3A···O4	0.88 (3)	2.36 (3)	2.918 (3)	121 (2)
N3—H3A···N2	0.88 (3)	2.01 (3)	2.865 (3)	162 (3)
N3—H3B···O3ⁱⁱⁱ	0.88 (3)	2.20 (3)	2.999 (3)	150 (3)
O5—H5B···O6	0.85 (4)	2.00 (4)	2.831 (3)	166 (3)
O5—H5A···O6^iv	0.92 (4)	1.96 (4)	2.833 (3)	157 (3)
O6—H6C···O3^v	0.93 (3)	1.85 (3)	2.779 (3)	173 (3)
O6—H6D···O3^vi	0.76 (3)	2.14 (3)	2.858 (3)	158 (4)
C6—H6B···O5^vii	0.97	2.53	3.348 (4)	141.7
C7—H7A···O1^viii	0.97	2.53	3.091 (3)	116.8

Symmetry codes: (i) x+1, y, z; (ii) x+1, −y+3/2, z+1/2; (iii) x, −y+3/2, z−1/2; (iv) −x, −y+1, −z+1; (v) −x+1, y−1/2, −z+1/2; (vi) x, −y+3/2, z+1/2; (vii) −x+1, −y+1, −z; (viii) x−1, −y+3/2, z−1/2.

Acknowledgements

This research was supported financially by Nanjing University of Posts and Telecommunications (grant No. NY209032).

References

Brandenburg, K. (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2000). SMART, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
King, P., Clèrac, R., Anson, C. E., Coulon, C. & Powell, A. K. (2003). Inorg. Chem. 42, 3492–3500. Web of Science CSD CrossRef PubMed CAS Google Scholar
Li, Z.-H. & Su, K.-M. (2007). Acta Cryst. E63, o4744. Web of Science CSD CrossRef IUCr Journals Google Scholar
Pan, L., Ching, N., Huang, X. Y. & Li, J. (2001). Chem. Eur. J. 7, 4431–4437. CrossRef PubMed CAS Google Scholar
Reviriego, F., Rodriguez-Franco, M. I., Navarro, P., Garcĺa-España, E., Liu-González, M., Verdejo, B. & Domènech, A. (2006). J. Am. Chem. Soc. 128, 16458–16459. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 10| October 2010| Page o2578

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

Piperazine-1,4-diium bis­­(2-carb­­oxy-1H-pyrazole-4-carboxyl­ate) tetra­hydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Piperazine-1,4-diium bis(2-carboxy-1H-pyrazole-4-carboxylate) tetrahydrate