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Acta Cryst. (2007). E63, m2468-m2469
https://doi.org/10.1107/S1600536807042651
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catena-Poly[piperazindiium [zincate(II)-bis­(μ-pyridine-2,3-dicarboxyl­ato)-κ3N,O2:O3;κ3O3:N,O2] tetra­hydrate]

H. Aghabozorg, S. Daneshvar, E. Motyeian, M. Ghadermazi and J. Attar Gharamaleki
The centrosymmetric title compound, {(C4H12N2)[Zn(C14H6N2O8)2]·4H2O}n or {(pipzH2)[Zn(py-2,3-dc)2]·4H2O}n, where py-2,3-dcH2 is pyridine-2,3-dicarboxylic acid and pipz is piperazine, was obtained by the reaction of zinc(II) nitrate tetra­hydrate with (pipzH2)(py-2,3-dc) as a proton-transfer compound in aqueous solution. Each ZnII (site symmetry {\overline 1}) is coordinated in a distorted octa­hedral geometry by four O atoms and two N atoms from two bidentate (py-2,3-dc)2− ligands, which also act as bridging ligands between ZnII atoms. The four donor atoms of the two coplanar (py-2,3-dc)2− anions form a square-planar arrangement around the ZnII centre. In the crystal structure, extensive O—H...O, N—H...O and C—H...O hydrogen bonds, as well as ion pairing and π–π stacking [with a distance of 3.8693 (8) Å between two aromatic rings] between different fragments, play an important role in the stabilization of the supra­molecular structure.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042651/om2156sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042651/om2156Isup2.hkl
Contains datablock I

CCDC reference: 663557

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.027
  • wR factor = 0.071
  • Data-to-parameter ratio = 19.4

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8


Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1         (2)       1.97


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check
Comment top

Here we report a new polymeric compound obtained from reaction of zinc(II) nitrate tetrahydrate with (pipzH2)(py-2,3-dc) as proton-transfer compound. The crystal structure of the title polymeric compound is shown in Fig. 1.Some selected bond distances and bond angles are listed in Table 1. The intermolecular hydrogen bond distances are listed in Table 2.

This compound crystallizes in the triclinic system, space group P1, with one formula in the unit cell. In anionic complex, [Zn(py-2,3-dc)2]2–, the ZnII (site symmetry 1) is hexacoordinated by two nitrogen atoms N1, and N1c (c: -x, -y, -z) and four oxygen atoms O1, O1c, O3a and O3d of carboxylate groups (a: x - 1, y, z; d: -x + 1, -y, -z) of two (py-2,3-dc)2- fragments which also act as bridging ligands between ZnII. O3a and O3d atoms from two neighbor (py-2,3-dc)2- fragments occupy the axial positions, while O1, O1c, N1, N1c from two (py-2,3-dc)2- fragments as bidentate ligands, form the equatorial plane. The N—Zn—N and O—Zn—O bond angles are linear. The four donor atoms of the two coplanar (py-2,3-dc)2- anions form a square-planar arrangement around the ZnII center.

The equatorial Zn—N and Zn—O bond lengths for Zn1 are 2.0543 (10) and 2.0605 (9) Å, respectively. The axial Zn—O bond length [2.2985 (9) Å] is significantly longer than equatorial bond lengths which is consistent with the corresponding data reported in literature (Aghabozorg, Sadr-khanlou et al., 2007). According to bond lengths, bond and torsion angles, arrangement of the six donor atoms around ZnII is a distorted octahedral. The angle between plane passing from pyridine ring (N1/C1—C5) and the plane passing carboxylate group (OCO) is 88.15 (3)°, indicating that these bridging carboxylate groups are almost perpendicular to the aromatic ring.

A considerable feature of the compound (I) is the presence of π–π stacking with distance of 3.8693 (8) Å (1 - x, -1 - y, -z) between two centroids of aromatic rings (Aghabozorg, Zabihi, et al., 2006) (Fig. 2).

In the crystal structure, the spaces between two layers of [Zn(py-2,3-dc)2]2– fragments are filled with layers of (pipzH2)2+ cations and uncoordinated water molecules (Fig. 3). The most important features of the crystal structure of (I) is the presence of a large number of O—H···O, N—H···O and C—H···O hydrogen bonds between (pipzH2)2+ and [Zn(py-2,3-dc)2]2– fragments and uncoordinated water molecules with D···A distances ranging from 2.746 (2) Å to 3.420 (2) Å (Table 2). Ion pairing and π–π stacking are also effective in the stabilization of the crystal structure. These interactions result in the formation of a supramolecular structure (Fig. 4).

Related literature top

We have reported cases in which proton transfer from pyridine-2,6-dicarboxylic acid (pydcH2) and benzene-1,2,4,5-tetracarboxylic acid (btcH4) to piperazine (pipz) and 1,10-phenanthroline (phen) resulted in the formation of novel self- assembled (pipzH2)(pydc) (Aghabozorg, Ghadermazi, Manteghi & Nakhjavan, 2006) and (phenH)4(btcH3)2(btcH2) (Aghabozorg, Ghadermazi & Attar Gharamaleki, 2006) systems, respectively. The resulting compounds, with some remaining sites as electron donors, can coordinate to metallic ions (Aghabozorg, Ghasemikhah, Ghadermazi et al., 2006; Aghabozorg, Ghasemikhah, Soleimannejad et al., 2006; Aghabozorg, Sadr-khanlou et al., 2007; Aghabozorg, Zabihi et al., 2006; Aghabozorg, Bahrami et al., 2007).

Experimental top

The proton-transfer ion pair was prepared by a reaction between piperazine and pyridine-2,3-dicarboxylic acid. Starting with a 1:1 molar ratio of the reactants in THF, a puffy white precipitate was obtained. By recrystallization in an aqueous solution, pale-yellow crystals were obtained. A solution of Zn(NO3)2.4H2O (130 mg, 0.5 mmol) in water (20 ml) was added to an aqueous solution of (pipzH2)(py-2,3-dc)(253 mg, 1.0 mmol) in water (20 ml) in a 1:2 molar ratio. Colorless crystals of (I) suitable for X-ray characterization were obtained after a few days at room temperature.

Refinement top

The hydrogen atoms of NH2 group and H2O were found in difference Fourier synthesis. The H(C) atom positions were calculated. All hydrogen atoms were refined in isotropic approximation in riding model with the Uiso(H) parameters equal to 1.2 Ueq(Ci) where Ueq(Ci) are the equivalent thermal parameters of the atoms to which corresponding H atoms are bonded.

Structure description top

Here we report a new polymeric compound obtained from reaction of zinc(II) nitrate tetrahydrate with (pipzH2)(py-2,3-dc) as proton-transfer compound. The crystal structure of the title polymeric compound is shown in Fig. 1.Some selected bond distances and bond angles are listed in Table 1. The intermolecular hydrogen bond distances are listed in Table 2.

This compound crystallizes in the triclinic system, space group P1, with one formula in the unit cell. In anionic complex, [Zn(py-2,3-dc)2]2–, the ZnII (site symmetry 1) is hexacoordinated by two nitrogen atoms N1, and N1c (c: -x, -y, -z) and four oxygen atoms O1, O1c, O3a and O3d of carboxylate groups (a: x - 1, y, z; d: -x + 1, -y, -z) of two (py-2,3-dc)2- fragments which also act as bridging ligands between ZnII. O3a and O3d atoms from two neighbor (py-2,3-dc)2- fragments occupy the axial positions, while O1, O1c, N1, N1c from two (py-2,3-dc)2- fragments as bidentate ligands, form the equatorial plane. The N—Zn—N and O—Zn—O bond angles are linear. The four donor atoms of the two coplanar (py-2,3-dc)2- anions form a square-planar arrangement around the ZnII center.

The equatorial Zn—N and Zn—O bond lengths for Zn1 are 2.0543 (10) and 2.0605 (9) Å, respectively. The axial Zn—O bond length [2.2985 (9) Å] is significantly longer than equatorial bond lengths which is consistent with the corresponding data reported in literature (Aghabozorg, Sadr-khanlou et al., 2007). According to bond lengths, bond and torsion angles, arrangement of the six donor atoms around ZnII is a distorted octahedral. The angle between plane passing from pyridine ring (N1/C1—C5) and the plane passing carboxylate group (OCO) is 88.15 (3)°, indicating that these bridging carboxylate groups are almost perpendicular to the aromatic ring.

A considerable feature of the compound (I) is the presence of π–π stacking with distance of 3.8693 (8) Å (1 - x, -1 - y, -z) between two centroids of aromatic rings (Aghabozorg, Zabihi, et al., 2006) (Fig. 2).

In the crystal structure, the spaces between two layers of [Zn(py-2,3-dc)2]2– fragments are filled with layers of (pipzH2)2+ cations and uncoordinated water molecules (Fig. 3). The most important features of the crystal structure of (I) is the presence of a large number of O—H···O, N—H···O and C—H···O hydrogen bonds between (pipzH2)2+ and [Zn(py-2,3-dc)2]2– fragments and uncoordinated water molecules with D···A distances ranging from 2.746 (2) Å to 3.420 (2) Å (Table 2). Ion pairing and π–π stacking are also effective in the stabilization of the crystal structure. These interactions result in the formation of a supramolecular structure (Fig. 4).

We have reported cases in which proton transfer from pyridine-2,6-dicarboxylic acid (pydcH2) and benzene-1,2,4,5-tetracarboxylic acid (btcH4) to piperazine (pipz) and 1,10-phenanthroline (phen) resulted in the formation of novel self- assembled (pipzH2)(pydc) (Aghabozorg, Ghadermazi, Manteghi & Nakhjavan, 2006) and (phenH)4(btcH3)2(btcH2) (Aghabozorg, Ghadermazi & Attar Gharamaleki, 2006) systems, respectively. The resulting compounds, with some remaining sites as electron donors, can coordinate to metallic ions (Aghabozorg, Ghasemikhah, Ghadermazi et al., 2006; Aghabozorg, Ghasemikhah, Soleimannejad et al., 2006; Aghabozorg, Sadr-khanlou et al., 2007; Aghabozorg, Zabihi et al., 2006; Aghabozorg, Bahrami et al., 2007).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL a.

Figures top
[Figure 1] Fig. 1. The structure of (I), showing the atom-numbering scheme and displacement. Ellipsoids are at the 50% probability level. Water molecules are omitted for clarity.Atoms marked with a, c, d and e suffixes are related by the symmetry codes: (a: x - 1, y, z; b: x + 1, y, z; c: -x, -y, -z; d: -x + 1, -y, -z; e: -x, -y, -z+1).
[Figure 2] Fig. 2. π-π Stacking interactions between two aromatic rings of (I), The average distance between the planes is 3.8693 (8) Å (1 - x, -1 - y, -z).
[Figure 3] Fig. 3. A layered packing diagram of (I). The space between the two layers of [Zn(py-2,3-dc)2]2– fragments is filled with a layer of (pipzH2)2+ cations and water molecules.
[Figure 4] Fig. 4. The crystal packing of (I), hydrogen bonds are shown as dashed lines.
catena-Poly[piperazindiium [zincate(II)-bis(µ-pyridine-2,3-dicarboxylato)- κ3N,O2:O3;κ3O3:N,O2] tetrahydrate] top
Crystal data top
(C4H12N2)[Zn(C14H6N2O8)2]·4H2OZ = 1
Mr = 555.80F(000) = 288
Triclinic, P1Dx = 1.731 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.6535 (6) ÅCell parameters from 3747 reflections
b = 8.4170 (8) Åθ = 2.6–30.1°
c = 10.3399 (9) ŵ = 1.23 mm−1
α = 78.493 (2)°T = 100 K
β = 79.524 (2)°Plate, colourless
γ = 71.284 (2)°0.35 × 0.31 × 0.20 mm
V = 533.07 (8) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3105 independent reflections
Radiation source: fine-focus sealed tube2876 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan
(APEX2; Bruker, 2005)		h = −9→9
Tmin = 0.673, Tmax = 0.791k = −11→11
6813 measured reflectionsl = −14→14
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: mixed
wR(F2) = 0.071H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0412P)2 + 0.2057P]
where P = (Fo2 + 2Fc2)/3
3105 reflections(Δ/σ)max < 0.001
160 parametersΔρmax = 0.45 e Å−3
0 restraintsΔρmin = −0.46 e Å−3
Crystal data top
(C4H12N2)[Zn(C14H6N2O8)2]·4H2Oγ = 71.284 (2)°
Mr = 555.80V = 533.07 (8) Å3
Triclinic, P1Z = 1
a = 6.6535 (6) ÅMo Kα radiation
b = 8.4170 (8) ŵ = 1.23 mm−1
c = 10.3399 (9) ÅT = 100 K
α = 78.493 (2)°0.35 × 0.31 × 0.20 mm
β = 79.524 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3105 independent reflections
Absorption correction: multi-scan
(APEX2; Bruker, 2005)		2876 reflections with I > 2σ(I)
Tmin = 0.673, Tmax = 0.791Rint = 0.020
6813 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0270 restraints
wR(F2) = 0.071H-atom parameters constrained
S = 1.01Δρmax = 0.45 e Å−3
3105 reflectionsΔρmin = −0.46 e Å−3
160 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
xyzUiso*/Ueq
Zn10.00000.00000.00000.01300 (7)
O10.19351 (14)0.09480 (11)−0.15435 (9)0.01152 (17)
O20.52743 (14)0.02875 (12)−0.25947 (9)0.01283 (18)
O30.96403 (14)−0.15685 (12)−0.14797 (9)0.01339 (18)
O40.87264 (15)−0.31878 (12)−0.25892 (9)0.01359 (18)
N10.28879 (16)−0.17768 (13)0.03105 (10)0.00907 (18)
C10.45027 (19)−0.15066 (15)−0.06130 (11)0.0087 (2)
C20.65942 (19)−0.25589 (15)−0.05727 (12)0.0084 (2)
C30.6983 (2)−0.38953 (16)0.04854 (12)0.0124 (2)
H3A0.8366−0.46130.05490.015*
C40.5320 (2)−0.41542 (16)0.14380 (12)0.0128 (2)
H4A0.5570−0.50340.21490.015*
C50.32724 (19)−0.30735 (16)0.13094 (12)0.0105 (2)
H5A0.2139−0.32540.19330.013*
C60.38876 (19)0.00268 (15)−0.16781 (12)0.0089 (2)
C70.84343 (19)−0.23815 (15)−0.16344 (12)0.0099 (2)
N1S−0.16806 (17)0.12631 (13)−0.56677 (10)0.0114 (2)
H2S−0.30410.1894−0.56870.014*
H1S−0.10030.1518−0.64650.014*
C1S−0.0706 (2)0.16761 (16)−0.46338 (13)0.0136 (2)
H1SA−0.15170.1488−0.37680.016*
H1SB−0.07500.2862−0.48280.016*
C2S0.1594 (2)0.05685 (16)−0.46129 (13)0.0124 (2)
H2SA0.24200.0797−0.54660.015*
H2SB0.22150.0831−0.39330.015*
O1W−0.42260 (15)0.66016 (12)−0.41719 (10)0.01514 (18)
H1W1−0.34780.6809−0.36780.018*
H2W1−0.35000.6226−0.48710.018*
O2W0.14990 (16)0.39242 (12)−0.35148 (9)0.01651 (19)
H1W20.07300.4798−0.31740.020*
H2W20.17940.3169−0.28400.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.00588 (10)0.01412 (11)0.01298 (11)0.00031 (7)0.00178 (7)0.00357 (7)
O10.0074 (4)0.0114 (4)0.0122 (4)−0.0002 (3)0.0000 (3)0.0010 (3)
O20.0097 (4)0.0146 (4)0.0111 (4)−0.0027 (3)0.0012 (3)0.0012 (3)
O30.0091 (4)0.0167 (4)0.0141 (4)−0.0053 (3)0.0007 (3)−0.0013 (3)
O40.0125 (4)0.0149 (4)0.0104 (4)−0.0006 (3)0.0010 (3)−0.0032 (3)
N10.0072 (4)0.0103 (4)0.0093 (4)−0.0026 (4)0.0000 (3)−0.0015 (3)
C10.0082 (5)0.0088 (5)0.0085 (5)−0.0020 (4)−0.0004 (4)−0.0018 (4)
C20.0076 (5)0.0091 (5)0.0085 (5)−0.0025 (4)−0.0001 (4)−0.0017 (4)
C30.0093 (5)0.0124 (5)0.0125 (5)−0.0010 (4)−0.0013 (4)0.0014 (4)
C40.0127 (5)0.0126 (5)0.0110 (5)−0.0030 (4)−0.0012 (4)0.0018 (4)
C50.0099 (5)0.0119 (5)0.0093 (5)−0.0043 (4)0.0009 (4)−0.0006 (4)
C60.0091 (5)0.0086 (5)0.0092 (5)−0.0027 (4)−0.0017 (4)−0.0013 (4)
C70.0064 (5)0.0101 (5)0.0090 (5)0.0010 (4)−0.0004 (4)0.0017 (4)
N1S0.0100 (5)0.0129 (5)0.0099 (4)−0.0031 (4)−0.0012 (4)0.0011 (4)
C1S0.0132 (6)0.0128 (5)0.0160 (6)−0.0044 (4)−0.0015 (4)−0.0044 (4)
C2S0.0123 (5)0.0131 (5)0.0131 (5)−0.0052 (4)−0.0025 (4)−0.0017 (4)
O1W0.0122 (4)0.0181 (5)0.0138 (4)−0.0042 (4)−0.0004 (3)−0.0009 (3)
O2W0.0215 (5)0.0121 (4)0.0123 (4)−0.0005 (4)−0.0012 (4)−0.0017 (3)
Geometric parameters (Å, º) top
Zn1—N1i2.0543 (10)C3—H3A0.9300
Zn1—N12.0543 (10)C4—C51.3869 (17)
Zn1—O12.0605 (9)C4—H4A0.9300
Zn1—O1i2.0605 (9)C5—H5A0.9300
Zn1—O3ii2.2984 (9)N1S—C1S1.4931 (16)
Zn1—O3iii2.2985 (9)N1S—C2Sv1.4948 (16)
O1—C61.2803 (14)N1S—H2S0.8919
O2—C61.2355 (15)N1S—H1S0.8863
O3—C71.2572 (15)C1S—C2S1.5160 (18)
O3—Zn1iv2.2985 (9)C1S—H1SA0.9700
O4—C71.2594 (15)C1S—H1SB0.9700
N1—C51.3381 (16)C2S—N1Sv1.4948 (16)
N1—C11.3472 (15)C2S—H2SA0.9700
C1—C21.3921 (16)C2S—H2SB0.9700
C1—C61.5179 (16)O1W—H1W10.8500
C2—C31.3980 (16)O1W—H2W10.8500
C2—C71.5131 (16)O2W—H1W20.8501
C3—C41.3839 (17)O2W—H2W20.8500
N1i—Zn1—N1180.00 (10)C5—C4—H4A120.7
N1i—Zn1—O199.34 (4)N1—C5—C4121.61 (11)
N1—Zn1—O180.66 (4)N1—C5—H5A119.2
N1i—Zn1—O1i80.66 (4)C4—C5—H5A119.2
N1—Zn1—O1i99.34 (4)O2—C6—O1125.37 (11)
O1—Zn1—O1i180.00 (7)O2—C6—C1118.55 (11)
N1i—Zn1—O3ii88.21 (4)O1—C6—C1116.08 (10)
N1—Zn1—O3ii91.79 (4)O3—C7—O4124.35 (11)
O1—Zn1—O3ii94.38 (3)O3—C7—C2119.85 (11)
O1i—Zn1—O3ii85.62 (3)O4—C7—C2115.61 (11)
N1i—Zn1—O3iii91.79 (4)C1S—N1S—C2Sv110.07 (10)
N1—Zn1—O3iii88.21 (4)C1S—N1S—H2S111.2
O1—Zn1—O3iii85.62 (3)C2Sv—N1S—H2S108.8
O1i—Zn1—O3iii94.38 (3)C1S—N1S—H1S109.5
O3ii—Zn1—O3iii180.00 (3)C2Sv—N1S—H1S111.3
C6—O1—Zn1114.73 (8)H2S—N1S—H1S105.9
C7—O3—Zn1iv140.01 (8)N1S—C1S—C2S109.90 (10)
C5—N1—C1120.13 (11)N1S—C1S—H1SA109.7
C5—N1—Zn1127.08 (8)C2S—C1S—H1SA109.7
C1—N1—Zn1112.76 (8)N1S—C1S—H1SB109.7
N1—C1—C2121.76 (11)C2S—C1S—H1SB109.7
N1—C1—C6115.51 (10)H1SA—C1S—H1SB108.2
C2—C1—C6122.72 (10)N1Sv—C2S—C1S110.09 (10)
C1—C2—C3117.62 (11)N1Sv—C2S—H2SA109.6
C1—C2—C7123.78 (11)C1S—C2S—H2SA109.6
C3—C2—C7118.54 (10)N1Sv—C2S—H2SB109.6
C4—C3—C2120.27 (11)C1S—C2S—H2SB109.6
C4—C3—H3A119.9H2SA—C2S—H2SB108.2
C2—C3—H3A119.9H1W1—O1W—H2W1113.2
C3—C4—C5118.57 (11)H1W2—O2W—H2W2103.3
C3—C4—H4A120.7
N1i—Zn1—O1—C6−175.52 (8)C1—C2—C3—C40.88 (18)
N1—Zn1—O1—C64.48 (8)C7—C2—C3—C4−176.55 (11)
O3ii—Zn1—O1—C695.58 (8)C2—C3—C4—C50.63 (19)
O3iii—Zn1—O1—C6−84.42 (8)C1—N1—C5—C40.91 (18)
O1—Zn1—N1—C5176.22 (11)Zn1—N1—C5—C4−177.46 (9)
O1i—Zn1—N1—C5−3.78 (11)C3—C4—C5—N1−1.56 (19)
O3ii—Zn1—N1—C582.07 (10)Zn1—O1—C6—O2174.12 (10)
O3iii—Zn1—N1—C5−97.93 (10)Zn1—O1—C6—C1−5.63 (13)
O1—Zn1—N1—C1−2.26 (8)N1—C1—C6—O2−176.02 (10)
O1i—Zn1—N1—C1177.74 (8)C2—C1—C6—O24.81 (17)
O3ii—Zn1—N1—C1−96.40 (8)N1—C1—C6—O13.75 (15)
O3iii—Zn1—N1—C183.60 (8)C2—C1—C6—O1−175.42 (11)
C5—N1—C1—C20.71 (17)Zn1iv—O3—C7—O4−177.67 (8)
Zn1—N1—C1—C2179.30 (9)Zn1iv—O3—C7—C2−2.98 (19)
C5—N1—C1—C6−178.48 (10)C1—C2—C7—O396.11 (14)
Zn1—N1—C1—C60.12 (12)C3—C2—C7—O3−86.63 (15)
N1—C1—C2—C3−1.58 (18)C1—C2—C7—O4−88.75 (14)
C6—C1—C2—C3177.55 (11)C3—C2—C7—O488.51 (14)
N1—C1—C2—C7175.70 (11)C2Sv—N1S—C1S—C2S58.59 (14)
C6—C1—C2—C7−5.17 (18)N1S—C1S—C2S—N1Sv−58.60 (14)
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y, −z; (iii) x−1, y, z; (iv) x+1, y, z; (v) −x, −y, −z−1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1S—H2S···O1Wvi0.891.872.753 (2)174
N1S—H1S···O3vii0.892.153.012 (1)164
N1S—H1S···O4vii0.892.353.054 (1)137
O1W—H1W1···O4viii0.852.012.842 (2)168
O1W—H2W1···O2Wix0.851.932.746 (2)159
O2W—H1W2···O4viii0.851.922.763 (1)172
O2W—H2W2···O10.852.062.868 (1)159
C2S—H2SA···O2vii0.972.433.298 (2)148
C2S—H2SA···O4vii0.972.583.264 (2)128
C2S—H2SB···O10.972.463.307 (2)145
C2S—H2SB···O20.972.543.420 (2)151
C4—H4A···O1Wi0.932.433.264 (2)150
Symmetry codes: (i) −x, −y, −z; (vi) −x−1, −y+1, −z−1; (vii) −x+1, −y, −z−1; (viii) x−1, y+1, z; (ix) −x, −y+1, −z−1.

Experimental details

Crystal data
Chemical formula(C4H12N2)[Zn(C14H6N2O8)2]·4H2O
Mr555.80
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)6.6535 (6), 8.4170 (8), 10.3399 (9)
α, β, γ (°)78.493 (2), 79.524 (2), 71.284 (2)
V (Å3)533.07 (8)
Z1
Radiation typeMo Kα
µ (mm−1)1.23
Crystal size (mm)0.35 × 0.31 × 0.20
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(APEX2; Bruker, 2005)
Tmin, Tmax0.673, 0.791
No. of measured, independent and
observed [I > 2σ(I)] reflections		6813, 3105, 2876
Rint0.020
(sin θ/λ)max (Å−1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.071, 1.01
No. of reflections3105
No. of parameters160
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.45, −0.46

Computer programs: APEX2 (Bruker, 2005), APEX2, SHELXTL (Sheldrick, 1998), SHELXTL a.

Selected geometric parameters (Å, º) top
Zn1—N12.0543 (10)Zn1—O3i2.2985 (9)
Zn1—O12.0605 (9)
N1ii—Zn1—O199.34 (4)N1—Zn1—O3i88.21 (4)
N1—Zn1—O180.66 (4)O1—Zn1—O3i85.62 (3)
N1ii—Zn1—O3i91.79 (4)O1ii—Zn1—O3i94.38 (3)
C2—C1—C6—O24.81 (17)C1—C2—C7—O396.11 (14)
C2—C1—C6—O1−175.42 (11)C1—C2—C7—O4−88.75 (14)
Symmetry codes: (i) x−1, y, z; (ii) −x, −y, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1S—H2S···O1Wiii0.891.872.753 (2)174
N1S—H1S···O3iv0.892.153.012 (1)164
N1S—H1S···O4iv0.892.353.054 (1)137
O1W—H1W1···O4v0.852.012.842 (2)168
O1W—H2W1···O2Wvi0.851.932.746 (2)159
O2W—H1W2···O4v0.851.922.763 (1)172
O2W—H2W2···O10.852.062.868 (1)159
C2S—H2SA···O2iv0.972.433.298 (2)148
C2S—H2SA···O4iv0.972.583.264 (2)128
C2S—H2SB···O10.972.463.307 (2)145
C2S—H2SB···O20.972.543.420 (2)151
C4—H4A···O1Wii0.932.433.264 (2)150
Symmetry codes: (ii) −x, −y, −z; (iii) −x−1, −y+1, −z−1; (iv) −x+1, −y, −z−1; (v) x−1, y+1, z; (vi) −x, −y+1, −z−1.
 

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