Ethyl­enediammonium bis­(5-methyl-3-oxo-2-phenyl-2,3-dihydro­pyrazol-1-ide): a hydrogen-bond-supported supra­molecular ionic assembly

Xu, R.; Xu, X.; Wang, D.; Yang, X.; Wang, X.

doi:10.1107/S1600536808026378

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages o1808-o1809

doi:10.1107/S1600536808026378

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Ethylenediammonium bis(5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-ide): a hydrogen-bond-supported supramolecular ionic assembly

Ruibo Xu,^a Xingyou Xu,^b Daqi Wang,^c Xujie Yang ^a ^* and Xin Wang ^a

^aMaterials Chemistry Laboratory, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China, ^bDepartment of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, and ^cCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: xuruibo9125@163.com

(Received 22 July 2008; accepted 15 August 2008; online 23 August 2008)

The title compound, C₂H₁₀N₂²⁺·2C₁₀H₉N₂O⁻, is composed of deprotonated 5-methyl-2-phenyl-1H-pyrazol-3(2H)-one anions (PMP⁻) and protonated ethylenediamine cations (H₂en²⁺). The ethylenediammonium ion is located on a crystallographic inversion center. The dihedral angle between the phenyl and pyrazole rings is 39.73 (8)°. The two components are connected through N—H⋯O and N—H⋯N hydrogen bonds, forming an infinite three-dimensional network.

Related literature

For related literature on pyrazolones, see: Cerchiaro et al. (2006 ). For conductivity data for ionic electrolytes, see: Kwak et al. (2004 ); Allmann et al. (1990 ). For background information on hydrogen bonds and their importance and applications, see: Fu et al. (2004 ); Hernández-Galindo et al. (2007 ); Hu et al. (2004 ); Li & Wang (2007 ); Peng et al. (2005 ); Yang et al. (2002 , 2005 , 2006 ); Zhou et al. (2006 ).

Experimental

Crystal data

C₂H₁₀N₂²⁺·2C₁₀H₉N₂O⁻
M_r = 408.50
Tetragonal, P 4₂ /n
a = 17.179 (2) Å
c = 7.0929 (15) Å
V = 2093.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.24 × 0.22 × 0.17 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: none
10541 measured reflections
1856 independent reflections
1284 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.141
S = 1.04
1856 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.89	1.94	2.743 (2)	149
N3—H3B⋯O1ⁱ	0.89	1.79	2.672 (2)	173
N3—H3C⋯N2ⁱⁱ	0.89	2.04	2.924 (3)	173
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[-y+{\script{1\over 2}}, x, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026378/zl2127sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026378/zl2127Isup2.hkl

checkCIF report

Comment top

Hydrogen bonds (H-bonds) are of importance in a large number of chemical and biological processes and in many practical applications (Li et al., 2007; Peng et al., 2005; Yang et al., 2006; Yang et al., 2002). Many interesting two- and three-dimensional frameworks have been designed and produced based on H-bonds (Fu et al., 2004; Hu et al., 2004; Zhou et al., 2006). The chemistry of pyrazylone and its derivatives is particularly interesting because of their potential application in medicinal chemistry (Cerchiaro et al., 2006), so 1-phenyl-3-methyl-pyrazole-5-one (PMP), which contains imino and carbonyl groups in its heterocycle, was choosen to react with the amino groups of ethylene diamine (en). The synthesis and crystal structure of the product of this reaction are reported here.

The title compound (Fig. 1) contains two crystallographically independent ions: the [H₂en]²⁺ cation which has two cationic ammonium groups, and the [PMP]^- anion. In the [PMP]^- anion, the bond length of C(1)—O(1) is 1.288 (3) Å, much shorter than that of C—O (1.43 Å), but close to that of C═O (1.22 Å) (Yang et al., 2005), indicating that the pyrazole-one ring of the title compound is present in the keto form, not the enol form. The N(2) atom of the deprotonated imino group of PMP is electron rich, therefore, the O atom of the carbonyl group and the N(2) atom of the pyrazole-one ring of the PMP molecule can be expected to be good hydrogen bond acceptors, while the H atoms of the [H₂en]²⁺ ammonium cations are expected to be good hydrogen donors. The Jeffrey criterion for H-bonds used by the International Union of Crystallography defines the largest distance between the hydrogen and the acceptor atoms as 2.60 Å for H···O and 2.63 Å for H···N, respectively (Hernández-Galindo et al., 2007). Compared to these data, the distances of H(3)···O(1) (-x+1, -y+1/2, -z) and H(3)···N(2)(x,-y+1/2, -z+1/2) for the title compound, respectively being 1.786 Å (or 1.940 Å) and 2.039 Å, are much shorter than the above-mentioned largest limit, providing a powerful evidence of the formation of H-bonds between these separate components.

There are no covalent interactions between the separate components of the title compound, but electrostatic and H-bonding interactions are present. All H atoms of the ammonium group, the O atom of the carbonyl group and the N atom of the deprotonated imino group in the title compound are engaged in intermolecular H-bonds which link the molecule into an extended three-dimensional network (Fig. 2). The H-bonds can be clearly seen in Fig. 2 to Fig. 5, and are summarized in Table 1. There are two kinds of H-bonds in the crystal structure: N—H···O and N—H···N. As shown in Fig. 3, the oxygen atom of the carbonyl group from [PMP]^- takes part in the H-bonding to the terminal nitrogen of [H₂en]²⁺, forming intermolecular N—H···O H-bonds that result in the formation of 8-membered rings. Each of the two ammonium groups of the [H₂en]²⁺ cation engages in these 8—membered rings, further linking the [H₂en]²⁺ and [PMP]^- ions into a two-dimensional network via these N—H···O H-bonds (Fig. 4). It can be seen from Fig. 5 that the nitrogen atom of the deprotonated imino group of [PMP]^- takes part in the H-bonding to the terminal nitrogen of [H₂en]²⁺, forming intermolecular N—H···N H-bonds. Therefore, through intermolecular N—H···O and N—H···N H-bonding interactions, each [PMP]^- anion is linked to three [H₂en]²⁺ cations and each [H₂en]²⁺ cation to six adjacent [PMP]^- anions. The two components thus construct a supramolecular assembly with a three-dimensional hydrogen bonded framework.

Related literature top

For related literature on pyrazolones, see: Cerchiaro et al. (2006); Allmann et al. (1990). For conductivity data for ionic electrolytes, see: Kwak et al. (2004). For background information on hydrogen bonds and their importance and applications, see: Fu et al. (2004); Hernández-Galindo et al. (2007); Hu et al. (2004); Li & Wang (2007); Peng et al. (2005); Yang et al. (2002, 2005, 2006); Zhou et al. (2006).

Experimental top

A solution of PMP (2 mmol in 10 ml anhydrous methanol) was added dropwise with constant stirring to the solution of en (2 mmol in 10 ml anhydrous methanol) at 323 K for 2 h. The resulting mixture was filtrated. After cooling, the filtrate was evaporated at ambient environment. Several days later, pink blocky crystals suitable for X-ray analysis were collected and washed with a small amount of methanol and dried at room temperature (yield 67%. m.p. 438–441 K). Anal. Calcd (%) for C₂₂H₂₈N₆O₂ (Mr = 408.5): C, 64.69; H, 6.91; N, 20.57. Found (%): C, 64.73; H, 6.97; N, 20.52. UV-vis (methanol): λ _max = 239 nm, ε = 2.655. The molar conductance of the compound in anhydrous methanol was 45.1 Ω ^-1cm²mol^-1, much lower than that expected for a 1:2 electrolyte, indicating that the compound is forming ion pairs and larger assemblies tightly bonded to each other by e.g. hydrogen bonds (Allmann et al., 1990; Kwak et al., 2004).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP drawing of the structure of the title compound with the atomic numbering scheme.
	Fig. 2. Stereoview and packing diagram for the title compound viewed along the c-axis.
	Fig. 3. Part of the crystal structure of the title compound, showing the 8-membered rings formed by N—H···O interactions. Dashed lines indicate H-bonds.
	Fig. 4. The crystal structure of title compound, showing the two-dimensional network parallel to the bc plane formed through N—H···O H-bond interactions. H-bonds are shown as dashed lines.
	Fig. 5. Part of the crystal structure of the title compound, showing the intermolecular N—H···N interactions. Dashed lines indicate H-bonds.

Ethylenediammonium bis(5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-ide) top

Crystal data top

C₂H₁₀N₂²⁺·2(C₁₀H₉N₂O⁻)	Melting point = 441–438 K
M_r = 408.50	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₂/n	Cell parameters from 2381 reflections
a = 17.179 (2) Å	θ = 3.1–24.1°
c = 7.0929 (15) Å	µ = 0.09 mm⁻¹
V = 2093.2 (6) Å³	T = 298 K
Z = 4	Block, pink
F(000) = 872	0.24 × 0.22 × 0.17 mm
D_x = 1.296 Mg m⁻³

Data collection top

Siemens SMART CCD area-detector diffractometer	1284 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.046
Graphite monochromator	θ_max = 25.0°, θ_min = 1.7°
ϕ and ω scans	h = −18→20
10541 measured reflections	k = −15→20
1856 independent reflections	l = −8→8

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0642P)² + 1.1449P] where P = (F_o² + 2F_c²)/3
1856 reflections	(Δ/σ)_max < 0.001
136 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂H₁₀N₂²⁺·2(C₁₀H₉N₂O⁻)	Z = 4
M_r = 408.50	Mo Kα radiation
Tetragonal, P4₂/n	µ = 0.09 mm⁻¹
a = 17.179 (2) Å	T = 298 K
c = 7.0929 (15) Å	0.24 × 0.22 × 0.17 mm
V = 2093.2 (6) Å³

Data collection top

Siemens SMART CCD area-detector diffractometer	1284 reflections with I > 2σ(I)
10541 measured reflections	R_int = 0.046
1856 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
1856 reflections	Δρ_min = −0.16 e Å⁻³
136 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
N1	0.50902 (11)	0.26458 (10)	0.1311 (3)	0.0316 (5)
N2	0.55431 (11)	0.19843 (11)	0.0995 (3)	0.0363 (5)
N3	0.45643 (11)	0.51464 (11)	0.2591 (3)	0.0329 (5)
H3A	0.4611	0.4662	0.2161	0.049*
H3B	0.4679	0.5481	0.1675	0.049*
H3C	0.4078	0.5226	0.2977	0.049*
O1	0.50279 (10)	0.39457 (9)	0.0303 (2)	0.0428 (5)
C1	0.53354 (13)	0.32631 (13)	0.0203 (3)	0.0320 (5)
C2	0.59414 (14)	0.29704 (13)	−0.0881 (3)	0.0354 (6)
H2	0.6225	0.3239	−0.1788	0.042*
C3	0.60418 (14)	0.21958 (13)	−0.0345 (3)	0.0364 (6)
C4	0.66173 (18)	0.16275 (17)	−0.1105 (4)	0.0579 (8)
H4A	0.6533	0.1128	−0.0533	0.087*
H4B	0.7135	0.1804	−0.0825	0.087*
H4C	0.6554	0.1585	−0.2446	0.087*
C5	0.46305 (12)	0.26868 (12)	0.2962 (3)	0.0298 (5)
C6	0.39474 (13)	0.31290 (14)	0.2980 (3)	0.0373 (6)
H6	0.3778	0.3380	0.1893	0.045*
C7	0.35267 (15)	0.31879 (15)	0.4635 (4)	0.0444 (7)
H7	0.3077	0.3489	0.4661	0.053*
C8	0.37619 (15)	0.28079 (15)	0.6244 (4)	0.0451 (7)
H8	0.3476	0.2857	0.7351	0.054*
C9	0.44250 (15)	0.23530 (14)	0.6208 (4)	0.0414 (6)
H9	0.4578	0.2085	0.7285	0.050*
C10	0.48621 (13)	0.22946 (13)	0.4580 (3)	0.0349 (6)
H10	0.5311	0.1993	0.4567	0.042*
C11	0.51023 (13)	0.52621 (14)	0.4182 (3)	0.0349 (6)
H11A	0.5080	0.5801	0.4588	0.042*
H11B	0.5630	0.5153	0.3773	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0388 (11)	0.0248 (10)	0.0314 (10)	0.0026 (8)	0.0055 (9)	0.0014 (8)
N2	0.0446 (12)	0.0273 (10)	0.0370 (11)	0.0061 (9)	0.0070 (9)	0.0007 (8)
N3	0.0364 (11)	0.0309 (10)	0.0313 (10)	0.0010 (8)	0.0033 (8)	0.0021 (8)
O1	0.0609 (11)	0.0284 (9)	0.0391 (10)	0.0102 (8)	0.0137 (8)	0.0063 (7)
C1	0.0414 (13)	0.0280 (12)	0.0266 (11)	−0.0013 (10)	−0.0001 (10)	0.0003 (9)
C2	0.0432 (14)	0.0328 (13)	0.0300 (12)	0.0004 (11)	0.0083 (10)	0.0022 (10)
C3	0.0410 (14)	0.0358 (13)	0.0324 (13)	0.0055 (11)	0.0017 (11)	−0.0037 (10)
C4	0.070 (2)	0.0500 (17)	0.0532 (17)	0.0183 (15)	0.0204 (15)	0.0015 (14)
C5	0.0292 (12)	0.0264 (12)	0.0338 (12)	−0.0034 (9)	0.0014 (10)	0.0002 (9)
C6	0.0349 (13)	0.0371 (13)	0.0398 (14)	0.0024 (11)	−0.0013 (11)	0.0043 (11)
C7	0.0378 (14)	0.0427 (15)	0.0526 (16)	0.0072 (11)	0.0107 (12)	0.0049 (13)
C8	0.0450 (15)	0.0485 (16)	0.0417 (15)	−0.0008 (12)	0.0152 (12)	0.0036 (12)
C9	0.0452 (15)	0.0442 (15)	0.0349 (14)	−0.0008 (12)	0.0026 (11)	0.0083 (11)
C10	0.0334 (13)	0.0324 (13)	0.0388 (14)	0.0009 (10)	−0.0004 (11)	0.0020 (10)
C11	0.0321 (12)	0.0387 (14)	0.0340 (13)	−0.0020 (10)	−0.0003 (10)	0.0026 (10)

Geometric parameters (Å, º) top

N1—C1	1.385 (3)	C4—H4C	0.9600
N1—N2	1.395 (2)	C5—C10	1.388 (3)
N1—C5	1.414 (3)	C5—C6	1.398 (3)
N2—C3	1.330 (3)	C6—C7	1.382 (3)
N3—C11	1.472 (3)	C6—H6	0.9300
N3—H3A	0.8900	C7—C8	1.375 (4)
N3—H3B	0.8900	C7—H7	0.9300
N3—H3C	0.8900	C8—C9	1.382 (4)
O1—C1	1.288 (3)	C8—H8	0.9300
C1—C2	1.389 (3)	C9—C10	1.381 (3)
C2—C3	1.394 (3)	C9—H9	0.9300
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.490 (3)	C11—C11ⁱ	1.510 (4)
C4—H4A	0.9600	C11—H11A	0.9700
C4—H4B	0.9600	C11—H11B	0.9700

C1—N1—N2	111.27 (17)	C10—C5—C6	119.8 (2)
C1—N1—C5	126.97 (18)	C10—C5—N1	120.0 (2)
N2—N1—C5	119.01 (17)	C6—C5—N1	120.2 (2)
C3—N2—N1	104.56 (18)	C7—C6—C5	119.1 (2)
C11—N3—H3A	109.5	C7—C6—H6	120.5
C11—N3—H3B	109.5	C5—C6—H6	120.5
H3A—N3—H3B	109.5	C8—C7—C6	121.1 (2)
C11—N3—H3C	109.5	C8—C7—H7	119.5
H3A—N3—H3C	109.5	C6—C7—H7	119.5
H3B—N3—H3C	109.5	C7—C8—C9	119.7 (2)
O1—C1—N1	122.8 (2)	C7—C8—H8	120.2
O1—C1—C2	131.9 (2)	C9—C8—H8	120.2
N1—C1—C2	105.35 (19)	C10—C9—C8	120.3 (2)
C1—C2—C3	106.7 (2)	C10—C9—H9	119.8
C1—C2—H2	126.6	C8—C9—H9	119.8
C3—C2—H2	126.6	C9—C10—C5	120.0 (2)
N2—C3—C2	112.1 (2)	C9—C10—H10	120.0
N2—C3—C4	120.4 (2)	C5—C10—H10	120.0
C2—C3—C4	127.5 (2)	N3—C11—C11ⁱ	111.2 (2)
C3—C4—H4A	109.5	N3—C11—H11A	109.4
C3—C4—H4B	109.5	C11ⁱ—C11—H11A	109.4
H4A—C4—H4B	109.5	N3—C11—H11B	109.4
C3—C4—H4C	109.5	C11ⁱ—C11—H11B	109.4
H4A—C4—H4C	109.5	H11A—C11—H11B	108.0
H4B—C4—H4C	109.5

C1—N1—N2—C3	−2.0 (2)	C1—N1—C5—C10	−130.8 (2)
C5—N1—N2—C3	−164.5 (2)	N2—N1—C5—C10	28.7 (3)
N2—N1—C1—O1	−177.0 (2)	C1—N1—C5—C6	48.4 (3)
C5—N1—C1—O1	−16.3 (4)	N2—N1—C5—C6	−152.1 (2)
N2—N1—C1—C2	2.0 (2)	C10—C5—C6—C7	2.1 (3)
C5—N1—C1—C2	162.8 (2)	N1—C5—C6—C7	−177.1 (2)
O1—C1—C2—C3	177.8 (2)	C5—C6—C7—C8	−1.2 (4)
N1—C1—C2—C3	−1.2 (3)	C6—C7—C8—C9	−0.6 (4)
N1—N2—C3—C2	1.3 (3)	C7—C8—C9—C10	1.6 (4)
N1—N2—C3—C4	−178.4 (2)	C8—C9—C10—C5	−0.8 (4)
C1—C2—C3—N2	−0.1 (3)	C6—C5—C10—C9	−1.1 (3)
C1—C2—C3—C4	179.6 (2)	N1—C5—C10—C9	178.1 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.89	1.94	2.743 (2)	149
N3—H3B···O1ⁱⁱ	0.89	1.79	2.672 (2)	173
N3—H3C···N2ⁱⁱⁱ	0.89	2.04	2.924 (3)	173

Symmetry codes: (ii) −x+1, −y+1, −z; (iii) −y+1/2, x, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂H₁₀N₂²⁺·2(C₁₀H₉N₂O⁻)
M_r	408.50
Crystal system, space group	Tetragonal, P4₂/n
Temperature (K)	298
a, c (Å)	17.179 (2), 7.0929 (15)
V (Å³)	2093.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.24 × 0.22 × 0.17

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10541, 1856, 1284
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.141, 1.04
No. of reflections	1856
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.16

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.89	1.94	2.743 (2)	149.2
N3—H3B···O1ⁱ	0.89	1.79	2.672 (2)	172.9
N3—H3C···N2ⁱⁱ	0.89	2.04	2.924 (3)	172.5

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −y+1/2, x, −z+1/2.

Acknowledgements

This project was supported by the Key Project for Fundamental Research of the Jiangsu Provincial Educational Committee (07 K J A150011) and the Natural Science Foundation of the Jiangsu Provincial Educational Committee (05KJB150003)

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Volume 64| Part 9| September 2008| Pages o1808-o1809

doi:10.1107/S1600536808026378

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

Ethyl­enedi­ammonium bis­­(5-methyl-3-oxo-2-phenyl-2,3-di­hydro­pyrazol-1-ide): a hydrogen-bond-supported supra­molecular ionic assembly

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethylenediammonium bis(5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-ide): a hydrogen-bond-supported supramolecular ionic assembly