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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 11| November 2012| Page m1429
doi:10.1107/S160053681204411X

Tetra­aqua­bis­­[2-(pyridin-4-yl-κN)pyrimidine-5-carboxyl­ato]zinc

Rupam Sen,a Dasarath Mal,a Paula Brandaoa and Zhi Lina*

aDepartment of Chemistry, CICECO, University of Aveiro, 3810-193 Portugal
*Correspondence e-mail: zlin@ua.pt

(Received 1 October 2012; accepted 24 October 2012; online 31 October 2012)

In the title complex, [Zn(C10H6N3O2)2(H2O)4], the ZnII ion lies on an inversion center and is coordinated in a slightly distorted octa­hedral geometry by two N atoms from two 2-(pyridin-4-yl)pyrimidine-5-carboxyl­ate ligands and four water mol­ecules. In the symmetry-unique part of the mol­ecule, the pyridine and pyrimidine rings form a dihedral angle of 7.0 (1)°. In the crystal, the coordinating water mol­ecules act as donor groups and carboxyl­ate O atoms act as acceptors in O—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For a general background to supra­molecular chemistry, see: Collet et al. (1996[Collet, A. (1996). Comprehensive Supramolecular Chemistry, edited by J. L. Atwood, J. E. D. Davies, D. D. M. Nicol, F. Vögtle & J. M. Lehn, Vol. 6, pp. 281-303. Oxford: Pergamon.]). For general syntheses and applications of MOFs, see: Sen et al. (2012[Sen, R., Saha, D. & Koner, S. (2012). Chem. Eur. J. 18, 5979-5986.]); Saha et al. (2012[Saha, D., Sen, R., Maity, T. & Koner, S. (2012). Dalton Trans. 41, 7399-7408.]). For a related structure, see: Piao & Xuan (2011[Piao, Y.-A. & Xuan, Z.-Y. (2011). Acta Cryst. E67, m1072.]).

[Scheme 1]

Experimental

Crystal data

  • [Zn(C10H6N3O2)2(H2O)4]

  • Mr = 537.79

  • Triclinic, [P \overline 1]

  • a = 6.2764 (7) Å

  • b = 6.9208 (7) Å

  • c = 12.7810 (17) Å

  • α = 99.676 (7)°

  • β = 92.638 (7)°

  • γ = 112.639 (5)°

  • V = 501.36 (10) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 1.29 mm−1

  • T = 150 K

  • 0.26 × 0.20 × 0.04 mm
Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.730, Tmax = 0.950

  • 8143 measured reflections

  • 2184 independent reflections

  • 2030 reflections with I > 2σ(I)

  • Rint = 0.032
Refinement

  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.089

  • S = 1.14

  • 2184 reflections

  • 176 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.05 e Å−3

  • Δρmin = −0.61 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1A⋯O16i 0.83 (2) 1.98 (2) 2.805 (3) 175 (3)
O1—H1B⋯O17ii 0.82 (3) 1.81 (3) 2.631 (3) 175 (4)
O2—H2A⋯O16iii 0.83 (4) 2.04 (4) 2.840 (3) 162 (4)
O2—H2B⋯O17iv 0.83 (3) 1.94 (3) 2.767 (3) 173 (3)
Symmetry codes: (i) x-1, y-1, z-1; (ii) -x+1, -y, -z+1; (iii) x-1, y, z-1; (iv) x, y, z-1.

Data collection: SMART (Bruker, 2008[Bruker (2008). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681204411X/lh5541sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204411X/lh5541Isup2.hkl

checkCIF report


Comment top

The aim of designing coordination frameworks is now been motivated through the field of supramolecular chemistry (Collet et al., 1996) and crystal engineering (Sen et al., 2012) from the viewpoints of the development of novel multi-functional MOFs. Fabricating MOFs with the desired properties are now the present day challenges of the chemist. N-Heterocyclic carboxylic acids share a major role in developing MOFs based material synthesis (Sen et al., 2012, Saha et al. 2012). Herein, we wish to report a new compound having an N-heterocyclic carboxylate ligand (2-pyridin-4-ylpyrimidine-5-carboxylato).

The molecular structure of the title compound is shown in Fig. 1. The ZnII ion lies on an inversion center and is coordinated in a slightly distorted octahedral geometry by two N atoms from two 2-pyridin-4-ylpyrimidine-5-carboxylato ligands and four water molecules. The equatorial plane is formed by the four water molecule and the two axial sites are occupied by the N-donor sites of the ligand. In the crystal, O—H···O hydrogen bonds form a three-dimensional network (Fig. 2). The related structure, tetraaquabis[4-(4H-1,2,4-triazol-4-yl)benzoato- κN1]manganese(II) decahydrate, has been published (Piao & Xuan, 2011).

Related literature top

For a general background to supramolecular chemistry, see: Collet et al. (1996). For general syntheses and applications of MOFs, see: Sen et al. (2012); Saha et al. (2012). For a related structure, see: Piao & Xuan (2011).

Experimental top

To prepare the complex we followed a routine hydrothermal process. Zn(NO3)2 hydrate and 2-pyridin-4-ylpyrimidine-5-carboxylic acid were mixed in a 1:1 ratio, and kept in a reaction bomb at 433 K for 2 days in autogenously created pressure. After cooling to room temperature colourless block-shaped crystals were obtained. Yield ca. 45% (based on metal). The crystals were collected by filtration, washed thoroughly with water and dried in ambient conditions.

Refinement top

The hydrogen atoms of the C—H bonds were placed at calculated positions and refined as riding atoms, with C—H = 0.95 Å with Uiso(H) =1.2Ueq(C) of the atom to which they are attached. The positions of the hydrogen atoms of the water molecules were discernible in difference Fourier maps and they were included in the structure refinement with individual isotropic thermal parameters and refined with an O—H distance restraint of 0.83 (2) Å.

Computing details top

Data collection: SMART (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level [Symmetry code: (i) -x,-y, -z].
[Figure 2] Fig. 2. Part of the crystal structure showing the three-dimensional hydrogen-bonded network.
Tetraaquabis[2-(pyridin-4-yl-κN)pyrimidine-5-carboxylato]zinc top
Crystal data top
[Zn(C10H6N3O2)2(H2O)4]Z = 1
Mr = 537.79F(000) = 276
Triclinic, P1Dx = 1.781 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.2764 (7) ÅCell parameters from 246 reflections
b = 6.9208 (7) Åθ = 2.6–27.6°
c = 12.7810 (17) ŵ = 1.29 mm−1
α = 99.676 (7)°T = 150 K
β = 92.638 (7)°Block, colourless
γ = 112.639 (5)°0.26 × 0.20 × 0.04 mm
V = 501.36 (10) Å3
Data collection top
Bruker SMART CCD
diffractometer		2184 independent reflections
Radiation source: fine-focus sealed tube2030 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
fine–focus sealed tube scansθmax = 27.4°, θmin = 3.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		h = −8→8
Tmin = 0.730, Tmax = 0.950k = −8→8
8143 measured reflectionsl = −16→16
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.14 w = 1/[σ2(Fo2) + (0.0522P)2 + 0.1478P]
where P = (Fo2 + 2Fc2)/3
2184 reflections(Δ/σ)max < 0.001
176 parametersΔρmax = 1.05 e Å−3
4 restraintsΔρmin = −0.61 e Å−3
Crystal data top
[Zn(C10H6N3O2)2(H2O)4]γ = 112.639 (5)°
Mr = 537.79V = 501.36 (10) Å3
Triclinic, P1Z = 1
a = 6.2764 (7) ÅMo Kα radiation
b = 6.9208 (7) ŵ = 1.29 mm−1
c = 12.7810 (17) ÅT = 150 K
α = 99.676 (7)°0.26 × 0.20 × 0.04 mm
β = 92.638 (7)°
Data collection top
Bruker SMART CCD
diffractometer		2184 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		2030 reflections with I > 2σ(I)
Tmin = 0.730, Tmax = 0.950Rint = 0.032
8143 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0334 restraints
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.14Δρmax = 1.05 e Å−3
2184 reflectionsΔρmin = −0.61 e Å−3
176 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
Zn0.00000.00000.00000.01467 (13)
O10.1899 (3)−0.1897 (2)−0.03156 (12)0.0170 (3)
H1A0.129 (5)−0.303 (3)−0.0767 (17)0.028 (7)*
H1B0.238 (6)−0.227 (6)0.0190 (19)0.051 (10)*
O20.2499 (3)0.2665 (3)−0.05357 (13)0.0196 (3)
H2A0.184 (5)0.334 (5)−0.080 (2)0.044 (9)*
H2B0.365 (4)0.265 (5)−0.082 (2)0.046 (10)*
N30.1681 (3)0.1214 (3)0.16096 (14)0.0152 (4)
C40.0418 (4)0.1047 (3)0.24398 (17)0.0165 (4)
H4−0.12160.06100.22960.020*
C50.1386 (4)0.1481 (3)0.34911 (16)0.0159 (4)
H50.04300.13340.40530.019*
C60.3782 (4)0.2137 (3)0.37137 (16)0.0138 (4)
C70.5107 (4)0.2394 (3)0.28616 (17)0.0167 (4)
H70.67510.28900.29850.020*
C80.3995 (4)0.1916 (3)0.18334 (17)0.0173 (4)
H80.49140.20940.12590.021*
C90.4895 (4)0.2521 (3)0.48227 (16)0.0148 (4)
N100.3511 (3)0.2432 (3)0.56043 (14)0.0167 (4)
C110.4536 (4)0.2753 (3)0.65945 (17)0.0169 (4)
H110.36200.26850.71690.020*
C120.6871 (4)0.3180 (3)0.68231 (16)0.0146 (4)
C130.8139 (4)0.3264 (4)0.59538 (17)0.0179 (4)
H130.97510.35710.60780.022*
N140.7165 (3)0.2928 (3)0.49487 (14)0.0179 (4)
C150.7950 (4)0.3495 (3)0.79525 (16)0.0166 (4)
O161.0133 (3)0.4300 (3)0.81382 (12)0.0203 (3)
O170.6557 (3)0.2901 (3)0.86250 (12)0.0214 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.01318 (19)0.0201 (2)0.01366 (19)0.00978 (14)0.00064 (12)0.00383 (13)
O10.0168 (7)0.0215 (8)0.0163 (8)0.0118 (7)−0.0000 (6)0.0033 (6)
O20.0167 (8)0.0232 (9)0.0225 (8)0.0101 (7)0.0040 (6)0.0086 (6)
N30.0151 (8)0.0197 (9)0.0140 (8)0.0103 (7)0.0014 (7)0.0033 (7)
C40.0140 (10)0.0187 (11)0.0192 (10)0.0090 (8)0.0020 (8)0.0038 (8)
C50.0160 (10)0.0186 (11)0.0160 (10)0.0091 (9)0.0040 (8)0.0048 (8)
C60.0168 (10)0.0114 (10)0.0157 (10)0.0080 (8)0.0011 (8)0.0036 (7)
C70.0132 (10)0.0192 (11)0.0198 (11)0.0088 (9)0.0016 (8)0.0036 (8)
C80.0161 (10)0.0213 (11)0.0163 (10)0.0092 (9)0.0035 (8)0.0038 (8)
C90.0162 (10)0.0140 (10)0.0166 (10)0.0079 (8)0.0014 (8)0.0044 (8)
N100.0160 (9)0.0193 (9)0.0170 (9)0.0089 (7)0.0017 (7)0.0051 (7)
C110.0185 (10)0.0178 (11)0.0161 (10)0.0084 (9)0.0022 (8)0.0051 (8)
C120.0161 (10)0.0130 (10)0.0174 (10)0.0082 (8)0.0004 (8)0.0046 (8)
C130.0158 (10)0.0213 (11)0.0190 (11)0.0100 (9)0.0006 (8)0.0045 (8)
N140.0159 (9)0.0225 (10)0.0170 (9)0.0094 (8)0.0008 (7)0.0045 (7)
C150.0201 (10)0.0160 (11)0.0177 (10)0.0118 (9)0.0008 (8)0.0030 (8)
O160.0170 (7)0.0255 (8)0.0198 (8)0.0100 (7)−0.0008 (6)0.0053 (6)
O170.0199 (8)0.0330 (9)0.0179 (8)0.0156 (7)0.0040 (6)0.0096 (6)
Geometric parameters (Å, º) top
Zn—O12.0923 (15)C6—C71.394 (3)
Zn—O1i2.0923 (15)C6—C91.486 (3)
Zn—N3i2.1419 (17)C7—C81.384 (3)
Zn—N32.1420 (17)C7—H70.9500
Zn—O2i2.1512 (15)C8—H80.9500
Zn—O22.1512 (15)C9—N141.338 (3)
O1—H1A0.830 (10)C9—N101.348 (3)
O1—H1B0.822 (10)N10—C111.336 (3)
O2—H2A0.833 (10)C11—C121.385 (3)
O2—H2B0.827 (10)C11—H110.9500
N3—C81.341 (3)C12—C131.392 (3)
N3—C41.347 (3)C12—C151.510 (3)
C4—C51.383 (3)C13—N141.340 (3)
C4—H40.9500C13—H130.9500
C5—C61.393 (3)C15—O161.257 (3)
C5—H50.9500C15—O171.258 (3)
O1—Zn—O1i180.0C4—C5—H5120.5
O1—Zn—N3i88.59 (6)C6—C5—H5120.5
O1i—Zn—N3i91.41 (6)C5—C6—C7118.01 (19)
O1—Zn—N391.41 (6)C5—C6—C9121.15 (18)
O1i—Zn—N388.59 (6)C7—C6—C9120.83 (19)
N3i—Zn—N3180.0C8—C7—C6119.2 (2)
O1—Zn—O2i86.31 (6)C8—C7—H7120.4
O1i—Zn—O2i93.69 (6)C6—C7—H7120.4
N3i—Zn—O2i91.45 (6)N3—C8—C7123.13 (19)
N3—Zn—O2i88.55 (6)N3—C8—H8118.4
O1—Zn—O293.69 (6)C7—C8—H8118.4
O1i—Zn—O286.31 (6)N14—C9—N10126.45 (19)
N3i—Zn—O288.55 (6)N14—C9—C6117.08 (18)
N3—Zn—O291.45 (6)N10—C9—C6116.48 (19)
O2i—Zn—O2180.0C11—N10—C9115.59 (19)
Zn—O1—H1A118 (2)N10—C11—C12123.16 (19)
Zn—O1—H1B118 (2)N10—C11—H11118.4
H1A—O1—H1B103 (3)C12—C11—H11118.4
Zn—O2—H2A110 (2)C11—C12—C13116.22 (19)
Zn—O2—H2B125 (2)C11—C12—C15121.41 (18)
H2A—O2—H2B114 (3)C13—C12—C15122.36 (19)
C8—N3—C4117.43 (18)N14—C13—C12122.3 (2)
C8—N3—Zn121.52 (14)N14—C13—H13118.8
C4—N3—Zn120.54 (14)C12—C13—H13118.8
N3—C4—C5123.19 (19)C9—N14—C13116.28 (18)
N3—C4—H4118.4O16—C15—O17125.88 (19)
C5—C4—H4118.4O16—C15—C12117.94 (18)
C4—C5—C6118.99 (19)O17—C15—C12116.18 (19)
Symmetry code: (i) −x, −y, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O16ii0.83 (2)1.98 (2)2.805 (3)175 (3)
O1—H1B···O17iii0.82 (3)1.81 (3)2.631 (3)175 (4)
O2—H2A···O16iv0.83 (4)2.04 (4)2.840 (3)162 (4)
O2—H2B···O17v0.83 (3)1.94 (3)2.767 (3)173 (3)
Symmetry codes: (ii) x−1, y−1, z−1; (iii) −x+1, −y, −z+1; (iv) x−1, y, z−1; (v) x, y, z−1.

Experimental details

Crystal data
Chemical formula[Zn(C10H6N3O2)2(H2O)4]
Mr537.79
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)6.2764 (7), 6.9208 (7), 12.7810 (17)
α, β, γ (°)99.676 (7), 92.638 (7), 112.639 (5)
V (Å3)501.36 (10)
Z1
Radiation typeMo Kα
µ (mm−1)1.29
Crystal size (mm)0.26 × 0.20 × 0.04
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.730, 0.950
No. of measured, independent and
observed [I > 2σ(I)] reflections		8143, 2184, 2030
Rint0.032
(sin θ/λ)max (Å−1)0.647
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.089, 1.14
No. of reflections2184
No. of parameters176
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)1.05, −0.61

Computer programs: SMART (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O16i0.83 (2)1.98 (2)2.805 (3)175 (3)
O1—H1B···O17ii0.82 (3)1.81 (3)2.631 (3)175 (4)
O2—H2A···O16iii0.83 (4)2.04 (4)2.840 (3)162 (4)
O2—H2B···O17iv0.83 (3)1.94 (3)2.767 (3)173 (3)
Symmetry codes: (i) x−1, y−1, z−1; (ii) −x+1, −y, −z+1; (iii) x−1, y, z−1; (iv) x, y, z−1.
 

Acknowledgements

RS wishes to thank FCT(SFRH/BPD/71798/2010) for a postdoctoral grant.

References

First citationBruker (2008). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCollet, A. (1996). Comprehensive Supramolecular Chemistry, edited by J. L. Atwood, J. E. D. Davies, D. D. M. Nicol, F. Vögtle & J. M. Lehn, Vol. 6, pp. 281–303. Oxford: Pergamon.  Google Scholar
 First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationPiao, Y.-A. & Xuan, Z.-Y. (2011). Acta Cryst. E67, m1072.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSaha, D., Sen, R., Maity, T. & Koner, S. (2012). Dalton Trans. 41, 7399–7408.  Web of Science CSD CrossRef CAS PubMed Google Scholar
 First citationSen, R., Saha, D. & Koner, S. (2012). Chem. Eur. J. 18, 5979–5986.  Web of Science CSD CrossRef CAS PubMed Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 11| November 2012| Page m1429
doi:10.1107/S160053681204411X
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