Bis(1-methyl-4-oxoimidazolidin-2-iminium) diaqua­bis­(pyridine-2,4-dicarboxyl­ato-κ2N,O2)zincate(II) dihydrate

Aghabozorg, H.; Jafarbak, F.; Mirzaei, M.; Notash, B.

doi:10.1107/S1600536811008452

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages m435-m436

doi:10.1107/S1600536811008452

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Bis(1-methyl-4-oxoimidazolidin-2-iminium) diaquabis(pyridine-2,4-dicarboxylato-κ²N,O²)zincate(II) dihydrate

Hossein Aghabozorg,^a ^* Fatemeh Jafarbak,^a Masoud Mirzaei ^b and Behrouz Notash ^c

^aFaculty of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, ^bDepartment of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad 917791436, Iran, and ^cDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: haghabozorg@yahoo.com

(Received 24 February 2011; accepted 6 March 2011; online 12 March 2011)

In the title compound, (C₄H₈N₃O)₂[Zn(C₇H₃NO₄)₂(H₂O)₂]·2H₂O, the Zn^II ion is six-coordinated in a distorted octahedral geometry by two pyridine-2,4-dicarboxylate (pydc) ligands in the equatorial plane and two water molecules in the axial positions. The pydc ligands act as bidentate chelating ligands through one carboxylate O atom and the pyridine N atom. Intermolecular N—H⋯O, O—H⋯O and weak C—H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For a review article on proton-transfer compounds, see: Aghabozorg et al. (2008b ). For related structures, see: Aghabozorg et al. (2008a ,c ); Attar Gharamaleki et al. (2009 ); Moghimi et al. (2004 , 2005 ).

Experimental

Crystal data

(C₄H₈N₃O)₂[Zn(C₇H₃NO₄)₂(H₂O)₂]·2H₂O
M_r = 695.93
Triclinic, $[P \overline 1]$
a = 5.3209 (11) Å
b = 8.3893 (17) Å
c = 16.621 (3) Å
α = 81.58 (3)°
β = 85.26 (3)°
γ = 74.09 (3)°
V = 705.1 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.96 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.15 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ) T_min = 0.793, T_max = 0.862
7743 measured reflections
3787 independent reflections
3206 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.090
S = 1.05
3787 reflections
226 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O3ⁱ	0.91 (3)	1.87 (3)	2.764 (2)	165 (3)
N4—H4A⋯O4ⁱ	0.86	1.86	2.706 (2)	168
N4—H4B⋯O2ⁱⁱ	0.86	1.92	2.771 (2)	169
O5—H5A⋯O4ⁱ	0.79 (2)	1.95 (3)	2.729 (2)	171 (3)
O5—H5B⋯O1ⁱⁱ	0.85 (3)	1.98 (3)	2.8088 (17)	165 (2)
O7—H7A⋯O3	0.73 (4)	2.32 (4)	2.968 (3)	148 (4)
O7—H7B⋯O6ⁱⁱⁱ	0.82 (4)	2.26 (4)	2.993 (3)	149 (4)
C5—H5⋯O5^iv	0.93	2.46	3.308 (2)	152
C11—H11A⋯O2ⁱⁱ	0.96	2.48	3.425 (3)	167
Symmetry codes: (i) x, y-1, z; (ii) x+1, y, z; (iii) -x, -y+1, -z; (iv) -x+2, -y, -z+1.

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008452/hy2411sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008452/hy2411Isup2.hkl

checkCIF report

Comment top

Many organic aromatic ligands and metal ions may aggregate into supramolecular networks using coordination and hydrogen bonds and π–π stacking interactions (Aghabozorg et al., 2008b). Metal complexes of pyridine-(di)carboxylates possess versatile structural motifs, which finally aggregate to various supramolecular architectures with interesting properties. We have previously reported several compounds containing creatinine (creat), pyridine-2,6-dicarboxylic acid (pydcH₂) and various metals, such as (creatH)(pydcH).H₂O (Moghimi et al., 2004), (creatH)₂[Bi(pydc)₂]₂.4H₂O (Moghimi et al., 2005), (creatH)[Zn(pydc)(pydcH)].4H₂O (Aghabozorg et al., 2008c), (creatH)[Cr(pydc)₂](pydcH₂).6H₂O (Aghabozorg et al., 2008a) and (H₃O)(creatH)[Ni(pydc)₂].3H₂O (Attar Gharamaleki et al., 2009). For more details and related literature see our recent review article on proton-transfer compounds (Aghabozorg et al., 2008b).

We describe here the crystal structure of the title compound. The compound contains a [Zn(pydc)₂(H₂O)₂]^2- anion, two (creatH)⁺ cations and two uncoordinated water molecules (Fig. 1). In the anion, the Zn^II atom is six-coordinated by two N atoms and two O atoms from two pydc ligands and two water molecules, with the bond length range of 2.0819 (14)–2.1957 (15) Å. The coordination environment around Zn^II is distorted octahedral. Intermolecular N—H···O, O—H···O, and weak C—H···O hydrogen bonds play an important role in the stabilization of the crystal structure (Fig. 2 and Table 1).

Related literature top

For a review article on proton-transfer compounds, see: Aghabozorg et al. (2008b). For related structures, see: Aghabozorg et al. (2008a,c); Attar Gharamaleki et al. (2009); Moghimi et al. (2004, 2005).

Experimental top

The reaction of pyridine-2,4-dicarboxylic acid (83 mg, 0.5 mmol) in 10 ml distilled water, creatinine (56 mg, 0.5 mmol) in 5 ml distilled water and Zn(NO₃)₂.4H₂O (65 mg, 0.25 mmol) in 10 ml distilled water in a 2:2:1 molar ratio gave colorless block crystals of the title compound after slow evaporation of the solvent at the room temperature. The crystals obtained were stable in air.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. [Symmetry code: (i) -x+1, -y, -z+1.]
	Fig. 2. The packing diagram of the title compound. Intermolecular hydrogen bonds are shown as blue dashed lines.

Bis(1-methyl-4-oxoimidazolidin-2-iminium) diaquabis(pyridine-2,4-dicarboxylato-κ²N,O²)zincate(II) dihydrate top

Crystal data top

(C₄H₈N₃O)₂[Zn(C₇H₃NO₄)₂(H₂O)₂]·2H₂O	Z = 1
M_r = 695.93	F(000) = 360.0
Triclinic, P1	D_x = 1.639 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3209 (11) Å	Cell parameters from 3787 reflections
b = 8.3893 (17) Å	θ = 2.5–29.2°
c = 16.621 (3) Å	µ = 0.96 mm⁻¹
α = 81.58 (3)°	T = 298 K
β = 85.26 (3)°	Block, colorless
γ = 74.09 (3)°	0.30 × 0.20 × 0.15 mm
V = 705.1 (3) Å³

Data collection top

Stoe IPDS-2 diffractometer	3787 independent reflections
Radiation source: fine-focus sealed tube	3206 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 29.2°, θ_min = 2.5°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	h = −7→7
T_min = 0.793, T_max = 0.862	k = −11→11
7743 measured reflections	l = −18→22

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.059P)²] where P = (F_o² + 2F_c²)/3
3787 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.46 e Å⁻³
1 restraint	Δρ_min = −0.48 e Å⁻³

Crystal data top

(C₄H₈N₃O)₂[Zn(C₇H₃NO₄)₂(H₂O)₂]·2H₂O	γ = 74.09 (3)°
M_r = 695.93	V = 705.1 (3) Å³
Triclinic, P1	Z = 1
a = 5.3209 (11) Å	Mo Kα radiation
b = 8.3893 (17) Å	µ = 0.96 mm⁻¹
c = 16.621 (3) Å	T = 298 K
α = 81.58 (3)°	0.30 × 0.20 × 0.15 mm
β = 85.26 (3)°

Data collection top

Stoe IPDS-2 diffractometer	3787 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	3206 reflections with I > 2σ(I)
T_min = 0.793, T_max = 0.862	R_int = 0.043
7743 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	1 restraint
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.46 e Å⁻³
3787 reflections	Δρ_min = −0.48 e Å⁻³
226 parameters

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

	x	y	z	U_iso*/U_eq
Zn1	0.5000	0.0000	0.5000	0.02707 (9)
O1	0.2451 (2)	0.02688 (14)	0.40534 (7)	0.0301 (2)
O2	0.1143 (3)	0.18980 (16)	0.28950 (8)	0.0395 (3)
O3	0.4093 (3)	0.72611 (16)	0.22032 (9)	0.0432 (3)
O4	0.7237 (3)	0.74523 (17)	0.29581 (9)	0.0462 (4)
O5	0.8365 (2)	−0.13001 (16)	0.42711 (8)	0.0325 (3)
O6	0.1878 (3)	0.07267 (19)	0.03511 (9)	0.0476 (3)
O7	0.0855 (4)	0.6692 (3)	0.09580 (15)	0.0641 (5)
N1	0.5314 (2)	0.22674 (15)	0.43582 (8)	0.0239 (2)
N2	0.6139 (3)	0.25207 (17)	0.11654 (9)	0.0313 (3)
N3	0.4814 (3)	0.02055 (17)	0.13579 (9)	0.0305 (3)
N4	0.7948 (3)	0.03970 (18)	0.22119 (10)	0.0379 (4)
H4B	0.8947	0.0943	0.2359	0.045*
H4A	0.7965	−0.0579	0.2462	0.045*
C1	0.3894 (3)	0.27280 (17)	0.36902 (9)	0.0228 (3)
C2	0.3856 (3)	0.41957 (18)	0.31741 (9)	0.0266 (3)
H2	0.2819	0.4505	0.2724	0.032*
C3	0.5398 (3)	0.51957 (17)	0.33430 (9)	0.0252 (3)
C4	0.6886 (3)	0.46909 (18)	0.40272 (10)	0.0282 (3)
H4	0.7951	0.5326	0.4151	0.034*
C5	0.6774 (3)	0.32360 (19)	0.45239 (10)	0.0277 (3)
H5	0.7746	0.2921	0.4988	0.033*
C6	0.2358 (3)	0.15364 (18)	0.35239 (9)	0.0251 (3)
C7	0.5555 (3)	0.67753 (19)	0.27867 (10)	0.0302 (3)
C8	0.6413 (3)	0.10458 (19)	0.16135 (10)	0.0275 (3)
C9	0.3457 (3)	0.1124 (2)	0.07056 (11)	0.0322 (3)
C10	0.4348 (3)	0.2712 (2)	0.05257 (11)	0.0348 (4)
H10A	0.5227	0.2790	−0.0008	0.042*
H10B	0.2887	0.3694	0.0555	0.042*
C11	0.7495 (4)	0.3769 (2)	0.12415 (12)	0.0360 (4)
H11A	0.8693	0.3364	0.1673	0.054*
H11B	0.6247	0.4781	0.1362	0.054*
H11C	0.8445	0.3988	0.0739	0.054*
H3	0.453 (6)	−0.081 (4)	0.155 (2)	0.076 (9)*
H7A	0.113 (8)	0.685 (5)	0.136 (2)	0.085 (13)*
H5B	0.952 (5)	−0.078 (3)	0.4112 (15)	0.048 (7)*
H7B	0.025 (7)	0.763 (5)	0.072 (2)	0.083 (11)*
H5A	0.818 (6)	−0.174 (3)	0.3900 (14)	0.060 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03224 (15)	0.02409 (13)	0.02854 (15)	−0.01705 (9)	−0.01220 (10)	0.00935 (9)
O1	0.0344 (6)	0.0286 (5)	0.0326 (6)	−0.0204 (4)	−0.0115 (5)	0.0074 (4)
O2	0.0513 (7)	0.0399 (6)	0.0359 (7)	−0.0273 (6)	−0.0237 (6)	0.0088 (5)
O3	0.0569 (8)	0.0353 (6)	0.0435 (7)	−0.0273 (6)	−0.0233 (6)	0.0156 (5)
O4	0.0700 (9)	0.0397 (7)	0.0419 (7)	−0.0400 (7)	−0.0218 (7)	0.0124 (5)
O5	0.0335 (6)	0.0362 (6)	0.0326 (6)	−0.0182 (5)	−0.0065 (5)	−0.0004 (5)
O6	0.0467 (8)	0.0542 (8)	0.0483 (8)	−0.0211 (6)	−0.0229 (6)	−0.0009 (7)
O7	0.0781 (13)	0.0550 (10)	0.0624 (12)	−0.0174 (9)	−0.0188 (10)	−0.0093 (9)
N1	0.0256 (6)	0.0233 (5)	0.0251 (6)	−0.0117 (4)	−0.0077 (5)	0.0029 (4)
N2	0.0348 (7)	0.0267 (6)	0.0343 (7)	−0.0152 (5)	−0.0096 (6)	0.0081 (5)
N3	0.0394 (7)	0.0280 (6)	0.0295 (7)	−0.0187 (5)	−0.0106 (6)	0.0031 (5)
N4	0.0529 (9)	0.0315 (7)	0.0369 (8)	−0.0264 (6)	−0.0225 (7)	0.0119 (6)
C1	0.0247 (6)	0.0227 (6)	0.0242 (7)	−0.0125 (5)	−0.0057 (5)	0.0013 (5)
C2	0.0323 (7)	0.0246 (6)	0.0254 (7)	−0.0140 (6)	−0.0099 (6)	0.0053 (5)
C3	0.0301 (7)	0.0208 (6)	0.0268 (7)	−0.0121 (5)	−0.0059 (6)	0.0028 (5)
C4	0.0328 (8)	0.0247 (7)	0.0321 (8)	−0.0164 (6)	−0.0092 (6)	0.0013 (6)
C5	0.0313 (7)	0.0266 (7)	0.0286 (7)	−0.0141 (6)	−0.0130 (6)	0.0041 (6)
C6	0.0269 (7)	0.0254 (6)	0.0273 (7)	−0.0149 (5)	−0.0071 (6)	0.0010 (5)
C7	0.0424 (9)	0.0228 (6)	0.0296 (8)	−0.0173 (6)	−0.0054 (6)	0.0024 (6)
C8	0.0335 (8)	0.0254 (7)	0.0269 (7)	−0.0152 (6)	−0.0047 (6)	0.0024 (6)
C9	0.0321 (8)	0.0349 (8)	0.0308 (8)	−0.0108 (6)	−0.0080 (6)	−0.0005 (6)
C10	0.0338 (8)	0.0338 (8)	0.0354 (9)	−0.0111 (6)	−0.0113 (7)	0.0094 (7)
C11	0.0402 (9)	0.0273 (7)	0.0435 (10)	−0.0180 (6)	−0.0069 (7)	0.0055 (7)

Geometric parameters (Å, º) top

Zn1—N1	2.0819 (14)	N3—H3	0.91 (4)
Zn1—O1	2.1087 (13)	N4—C8	1.298 (2)
Zn1—O5	2.1957 (15)	N4—H4B	0.8600
O1—C6	1.2696 (18)	N4—H4A	0.8600
O2—C6	1.2303 (19)	C1—C2	1.390 (2)
O3—C7	1.244 (2)	C1—C6	1.520 (2)
O4—C7	1.254 (2)	C2—C3	1.393 (2)
O5—H5B	0.85 (3)	C2—H2	0.9300
O5—H5A	0.79 (2)	C3—C4	1.387 (2)
O6—C9	1.207 (2)	C3—C7	1.519 (2)
O7—H7A	0.74 (4)	C4—C5	1.383 (2)
O7—H7B	0.82 (4)	C4—H4	0.9300
N1—C5	1.3367 (19)	C5—H5	0.9300
N1—C1	1.3437 (19)	C9—C10	1.514 (3)
N2—C8	1.325 (2)	C10—H10A	0.9700
N2—C10	1.449 (2)	C10—H10B	0.9700
N2—C11	1.449 (2)	C11—H11A	0.9600
N3—C9	1.368 (2)	C11—H11B	0.9600
N3—C8	1.370 (2)	C11—H11C	0.9600

N1—Zn1—N1ⁱ	180.000 (1)	C1—C2—H2	120.6
N1—Zn1—O1	79.39 (5)	C3—C2—H2	120.6
N1ⁱ—Zn1—O1	100.61 (5)	C4—C3—C2	118.38 (13)
N1—Zn1—O1ⁱ	100.61 (5)	C4—C3—C7	119.66 (14)
N1ⁱ—Zn1—O1ⁱ	79.39 (5)	C2—C3—C7	121.92 (14)
O1—Zn1—O1ⁱ	180.00 (4)	C5—C4—C3	119.50 (14)
N1—Zn1—O5	89.26 (6)	C5—C4—H4	120.2
N1ⁱ—Zn1—O5	90.74 (6)	C3—C4—H4	120.2
O1—Zn1—O5	91.70 (5)	N1—C5—C4	122.15 (14)
O1ⁱ—Zn1—O5	88.30 (5)	N1—C5—H5	118.9
N1—Zn1—O5ⁱ	90.74 (6)	C4—C5—H5	118.9
N1ⁱ—Zn1—O5ⁱ	89.26 (6)	O2—C6—O1	126.60 (14)
O1—Zn1—O5ⁱ	88.30 (5)	O2—C6—C1	117.01 (13)
O1ⁱ—Zn1—O5ⁱ	91.70 (5)	O1—C6—C1	116.38 (13)
O5—Zn1—O5ⁱ	180.000 (1)	O3—C7—O4	125.95 (15)
C6—O1—Zn1	114.83 (9)	O3—C7—C3	118.71 (14)
Zn1—O5—H5B	116.8 (17)	O4—C7—C3	115.32 (14)
Zn1—O5—H5A	121 (2)	N4—C8—N2	127.93 (15)
H5B—O5—H5A	106 (3)	N4—C8—N3	121.60 (14)
H7A—O7—H7B	103 (4)	N2—C8—N3	110.47 (13)
C5—N1—C1	118.96 (13)	O6—C9—N3	126.13 (17)
C5—N1—Zn1	127.89 (10)	O6—C9—C10	127.74 (16)
C1—N1—Zn1	113.12 (10)	N3—C9—C10	106.12 (14)
C8—N2—C10	110.12 (14)	N2—C10—C9	102.65 (13)
C8—N2—C11	127.22 (14)	N2—C10—H10A	111.2
C10—N2—C11	122.56 (14)	C9—C10—H10A	111.2
C9—N3—C8	110.51 (14)	N2—C10—H10B	111.2
C9—N3—H3	118 (2)	C9—C10—H10B	111.2
C8—N3—H3	131 (2)	H10A—C10—H10B	109.2
C8—N4—H4B	120.0	N2—C11—H11A	109.5
C8—N4—H4A	120.0	N2—C11—H11B	109.5
H4B—N4—H4A	120.0	H11A—C11—H11B	109.5
N1—C1—C2	122.12 (13)	N2—C11—H11C	109.5
N1—C1—C6	116.08 (12)	H11A—C11—H11C	109.5
C2—C1—C6	121.80 (13)	H11B—C11—H11C	109.5
C1—C2—C3	118.85 (13)

N1—Zn1—O1—C6	3.82 (11)	C3—C4—C5—N1	1.5 (3)
N1ⁱ—Zn1—O1—C6	−176.18 (11)	Zn1—O1—C6—O2	175.35 (14)
O5—Zn1—O1—C6	−85.11 (12)	Zn1—O1—C6—C1	−5.02 (18)
O5ⁱ—Zn1—O1—C6	94.89 (12)	N1—C1—C6—O2	−176.70 (15)
O1—Zn1—N1—C5	−179.66 (15)	C2—C1—C6—O2	2.4 (2)
O1ⁱ—Zn1—N1—C5	0.34 (15)	N1—C1—C6—O1	3.6 (2)
O5—Zn1—N1—C5	−87.80 (14)	C2—C1—C6—O1	−177.22 (14)
O5ⁱ—Zn1—N1—C5	92.20 (14)	C4—C3—C7—O3	−175.83 (16)
O1—Zn1—N1—C1	−1.69 (11)	C2—C3—C7—O3	6.3 (3)
O1ⁱ—Zn1—N1—C1	178.31 (11)	C4—C3—C7—O4	5.8 (2)
O5—Zn1—N1—C1	90.17 (11)	C2—C3—C7—O4	−172.14 (17)
O5ⁱ—Zn1—N1—C1	−89.83 (11)	C10—N2—C8—N4	176.19 (18)
C5—N1—C1—C2	−1.2 (2)	C11—N2—C8—N4	−0.2 (3)
Zn1—N1—C1—C2	−179.41 (12)	C10—N2—C8—N3	−3.2 (2)
C5—N1—C1—C6	177.91 (14)	C11—N2—C8—N3	−179.64 (17)
Zn1—N1—C1—C6	−0.26 (17)	C9—N3—C8—N4	−178.09 (16)
N1—C1—C2—C3	1.9 (2)	C9—N3—C8—N2	1.4 (2)
C6—C1—C2—C3	−177.24 (14)	C8—N3—C9—O6	−179.20 (18)
C1—C2—C3—C4	−0.8 (2)	C8—N3—C9—C10	1.0 (2)
C1—C2—C3—C7	177.16 (15)	C8—N2—C10—C9	3.57 (19)
C2—C3—C4—C5	−0.8 (2)	C11—N2—C10—C9	−179.80 (16)
C7—C3—C4—C5	−178.81 (15)	O6—C9—C10—N2	177.51 (19)
C1—N1—C5—C4	−0.5 (2)	N3—C9—C10—N2	−2.67 (19)
Zn1—N1—C5—C4	177.40 (12)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3ⁱⁱ	0.91 (3)	1.87 (3)	2.764 (2)	165 (3)
N4—H4A···O4ⁱⁱ	0.86	1.86	2.706 (2)	168
N4—H4B···O2ⁱⁱⁱ	0.86	1.92	2.771 (2)	169
O5—H5A···O4ⁱⁱ	0.79 (2)	1.95 (3)	2.729 (2)	171 (3)
O5—H5B···O1ⁱⁱⁱ	0.85 (3)	1.98 (3)	2.8088 (17)	165 (2)
O7—H7A···O3	0.73 (4)	2.32 (4)	2.968 (3)	148 (4)
O7—H7B···O6^iv	0.82 (4)	2.26 (4)	2.993 (3)	149 (4)
C5—H5···O5^v	0.93	2.46	3.308 (2)	152
C11—H11A···O2ⁱⁱⁱ	0.96	2.48	3.425 (3)	167

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

Experimental details

Crystal data
Chemical formula	(C₄H₈N₃O)₂[Zn(C₇H₃NO₄)₂(H₂O)₂]·2H₂O
M_r	695.93
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	5.3209 (11), 8.3893 (17), 16.621 (3)
α, β, γ (°)	81.58 (3), 85.26 (3), 74.09 (3)
V (Å³)	705.1 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.96
Crystal size (mm)	0.30 × 0.20 × 0.15

Data collection
Diffractometer	Stoe IPDS2 diffractometer
Absorption correction	Numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)
T_min, T_max	0.793, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	7743, 3787, 3206
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.090, 1.05
No. of reflections	3787
No. of parameters	226
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.48

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3ⁱ	0.91 (3)	1.87 (3)	2.764 (2)	165 (3)
N4—H4A···O4ⁱ	0.86	1.8600	2.706 (2)	168
N4—H4B···O2ⁱⁱ	0.86	1.9200	2.771 (2)	169
O5—H5A···O4ⁱ	0.79 (2)	1.95 (3)	2.729 (2)	171 (3)
O5—H5B···O1ⁱⁱ	0.85 (3)	1.98 (3)	2.8088 (17)	165 (2)
O7—H7A···O3	0.73 (4)	2.32 (4)	2.968 (3)	148 (4)
O7—H7B···O6ⁱⁱⁱ	0.82 (4)	2.26 (4)	2.993 (3)	149 (4)
C5—H5···O5^iv	0.93	2.4600	3.308 (2)	152
C11—H11A···O2ⁱⁱ	0.96	2.4800	3.425 (3)	167

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

Acknowledgements

We are grateful to the Islamic Azad University, North Tehran Branch, for financial support.

References

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