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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 64| Part 6| June 2008| Page m808
doi:10.1107/S1600536808013688

Poly[aqua­[μ3-5-(2-carboxyl­atophen­yl)-1H-tetra­zolato]zinc(II)]

Xiu-Zhi Lia and Zhi-Rong Qua*

aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: quzr@seu.edu.cn

(Received 19 April 2008; accepted 8 May 2008; online 14 May 2008)

The title coordination polymer, [Zn(C8H4N4O2)(H2O)]n, was prepared by the hydro­thermal reaction of zinc nitrate and 2-(1H-tetra­zol-5-yl)benzoic acid. Two types of coordinated zinc cations exist in the structure. One is tetra­hedrally coordinated by two O and two N from two ligands, the other is octa­hedrally coordinated by two N and two O from two ligands at equatorial sites and by two O atoms of water mol­ecules at axial sites, resulting in a two-dimensional framework. The crystal structure is stabilized by intra­molecular O—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For the chemistry of tetra­zoles, see: Xiong et al. (2002[Xiong, R.-G., Xue, X., Zhao, H., You, X.-Z., Abrahams, B. F. & Xue, Z.-L. (2002). Angew. Chem. Int. Ed. 41, 3800-3803.]); Xue et al. (2002[Xue, X., Wang, X.-S., Wang, L.-Z., Xiong, R.-G., Abrahams, B. F., You, X.-Z., Xue, Z.-L. & Che, C.-M. (2002). Inorg. Chem. 41, 3800-3803.]); Dunica et al. (1991[Dunica, J. V., Pierce, M. E. & Santella, J. B. III (1991). J. Org. Chem. 56, 2395-2400.]); Wang et al. (2005[Wang, X.-S., Tang, Y.-Z., Huang, X.-F., Qu, Z.-R., Che, C.-M., Chan, C. W. H. & Xiong, R.-G. (2005). Inorg. Chem. 44, 5278-5285.]); Wittenberger et al. (1993[Wittenberger, S. J. & Donner, B. G. (1993). J. Org. Chem. 58, 4139-4141.]); Hu et al. (2007[Hu, B., Xu, X.-B., Li, Y.-X. & Ye, H.-Y. (2007). Acta Cryst. E63, m2698.]). For the crystal structure of a related compound, see: Li et al. (2005[Li, J.-T., Tao, J., Huang, R.-B. & Zhang, L.-S. (2005). Acta Cryst. E61, m984-m985.]).

[Scheme 1]

Experimental

Crystal data

  • [Zn(C8H4N4O2)(H2O)]

  • Mr = 271.56

  • Monoclinic, C 2/c

  • a = 19.696 (8) Å

  • b = 7.1340 (18) Å

  • c = 14.932 (6) Å

  • β = 114.39 (2)°

  • V = 1910.9 (12) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 2.57 mm−1

  • T = 293 (2) K

  • 0.07 × 0.07 × 0.06 mm
Data collection

  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.835, Tmax = 0.860

  • 9320 measured reflections

  • 2173 independent reflections

  • 1623 reflections with I > 2σ(I)

  • Rint = 0.085
Refinement

  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.112

  • S = 1.08

  • 2173 reflections

  • 147 parameters

  • H-atom parameters constrained

  • Δρmax = 0.63 e Å−3

  • Δρmin = −0.60 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1W—H1W⋯O1i 0.82 2.08 2.804 (4) 147
O1W—H2W⋯N3ii 0.79 2.25 2.976 (5) 155
Symmetry codes: (i) [x, -y, z+{\script{1\over 2}}]; (ii) -x+2, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808013688/rz2210sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013688/rz2210Isup2.hkl

checkCIF report


Comment top

Coordination frameworks have received much attention over the past decade because of their potential applications. Multifunctional organic ligands are necessary to construct such frameworks. 2-(1H-Tetrazol-5-yl)benzoic acid is a ligand with two functional groups, a carboxylate group and a tetrazole ring. Tetrazole compounds have a wide range of applications in coordination chemistry, medicinal chemistry and material science (Hu, et al., 2007; Xiong, et al., 2002; Xue, et al., 2002; Wang, et al., 2005; Dunica, et al., 1991; Wittenberger & Donner, 1993). We report here the crystal structure of the title compound, which was obtained by the hydrothermal reaction of zinc nitrate and 2-(1H-tetrazol-5-yl)benzoic acid.

In the structure of the title compound, two types of coordinated zinc cations exist (Fig. 1). Zn1 is tetrahedrally coordinated by two O and two N from two ligands, while Zn2 is octahedrally coordinated, with two N and two O from two ligands at equatorial sites and two O atoms of H2O molecules at axial sites, resulting in a two-dimensional framework (Fig 2). Bond lengths and angles in the compound are within normal ranges (Li et al., 2005). The crystal structure is stabilized by intramolecular O—H···O and O—H···N hydrogen bonds (Table 1).

Related literature top

For the chemistry of tetrazoles, see: Xiong et al. (2002); Xue et al. (2002); Dunica et al. (1991); Wang et al. (2005); Wittenberger et al. (1993); Hu et al. (2007). For the crystal structure of a related compound, see: Li et al. (2005).

Experimental top

A mixture of Zn(NO3)2 (0.2 mmol) and 2-(1H-tetrazol-5-yl)benzoic acid (0.2 mmol) in H2O (4 ml) was heated in Pyrex tube at 100°C for two days. After slowly cooling down to room temperature over a period of 12 h, colourless crystals of the title compound suitable for diffraction were isolated.

Refinement top

Positional parameters of all the H atoms were calculated geometrically and were allowed to ride on their parent atoms, with C—H = 0.93 Å, O—H = 0.81Å and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(O).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. A partial packing diagram of the title compound, with displacement ellipsoids drawn at the 30% probability level. H atoms are omitted for clarity. [Symmetry codes: (A) 2-x, -y, 1-z; (B) x, y-1, z; (C) 2-x, y-1, 1/2-z; (D) 2-x, y, 1/2-z].
[Figure 2] Fig. 2. Packing diagram of the title compound, showing the structure along the b axis. H atoms are omitted for clarity.
Poly[aqua[µ3-5-(2-carboxylatophenyl)-1H-tetrazolato]zinc(II)] top
Crystal data top
[Zn(C8H4N4O2)(H2O)]F(000) = 1088.0
Mr = 271.56Dx = 1.888 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1979 reflections
a = 19.696 (8) Åθ = 3.1–27.5°
b = 7.1340 (18) ŵ = 2.57 mm−1
c = 14.932 (6) ÅT = 293 K
β = 114.39 (2)°Block, colourless
V = 1910.9 (12) Å30.07 × 0.07 × 0.06 mm
Z = 8
Data collection top
Rigaku SCXmini
diffractometer		2173 independent reflections
Radiation source: fine-focus sealed tube1623 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.085
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = −25→25
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −9→9
Tmin = 0.835, Tmax = 0.860l = −19→19
9320 measured reflections
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0929P)2 + 0.0509P]
whereP = (Fo2 + 2Fc2)/3
2173 reflections(Δ/σ)max < 0.001
147 parametersΔρmax = 0.63 e Å−3
0 restraintsΔρmin = −0.60 e Å−3
Crystal data top
[Zn(C8H4N4O2)(H2O)]V = 1910.9 (12) Å3
Mr = 271.56Z = 8
Monoclinic, C2/cMo Kα radiation
a = 19.696 (8) ŵ = 2.57 mm−1
b = 7.1340 (18) ÅT = 293 K
c = 14.932 (6) Å0.07 × 0.07 × 0.06 mm
β = 114.39 (2)°
Data collection top
Rigaku SCXmini
diffractometer		2173 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		1623 reflections with I > 2σ(I)
Tmin = 0.835, Tmax = 0.860Rint = 0.085
9320 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 1.08Δρmax = 0.63 e Å−3
2173 reflectionsΔρmin = −0.60 e Å−3
147 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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
Zn11.0000−0.31787 (9)0.25000.0245 (2)
Zn21.00000.00000.50000.0242 (2)
C10.9761 (2)0.3503 (5)0.3649 (3)0.0202 (8)
C20.8990 (2)0.3170 (6)0.2905 (3)0.0213 (8)
C30.8527 (2)0.4731 (6)0.2629 (3)0.0289 (10)
H30.86930.58590.29590.035*
C40.7821 (3)0.4630 (6)0.1866 (4)0.0383 (12)
H40.75140.56810.16930.046*
C50.7577 (3)0.2978 (7)0.1370 (4)0.0410 (12)
H50.71040.29100.08580.049*
C60.8032 (3)0.1407 (6)0.1630 (3)0.0339 (11)
H60.78640.02990.12790.041*
C70.8733 (2)0.1459 (6)0.2405 (3)0.0222 (9)
C80.9165 (2)−0.0327 (5)0.2671 (3)0.0217 (9)
N11.0151 (2)0.2573 (5)0.4466 (2)0.0241 (8)
N21.0788 (2)0.3533 (5)0.4939 (3)0.0295 (9)
N31.0792 (2)0.4999 (5)0.4424 (3)0.0280 (8)
N41.01491 (19)0.5018 (4)0.3598 (2)0.0220 (7)
O10.91662 (17)−0.1326 (4)0.1958 (2)0.0270 (7)
O20.94994 (17)−0.0846 (4)0.3536 (2)0.0314 (7)
O1W0.89412 (16)0.0990 (4)0.4984 (2)0.0322 (7)
H1W0.89130.06810.54970.048*
H2W0.88720.20610.50350.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0335 (4)0.0167 (3)0.0215 (4)0.0000.0097 (3)0.000
Zn20.0341 (4)0.0186 (4)0.0186 (4)−0.0009 (3)0.0097 (3)0.0027 (3)
C10.026 (2)0.0153 (19)0.021 (2)−0.0018 (17)0.0104 (17)0.0000 (16)
C20.021 (2)0.022 (2)0.0183 (19)−0.0016 (17)0.0057 (17)0.0025 (16)
C30.032 (2)0.023 (2)0.030 (2)0.0042 (19)0.011 (2)0.0001 (18)
C40.031 (3)0.033 (3)0.045 (3)0.013 (2)0.009 (2)0.003 (2)
C50.026 (2)0.043 (3)0.039 (3)0.004 (2)−0.002 (2)−0.001 (2)
C60.029 (2)0.029 (2)0.035 (3)0.001 (2)0.004 (2)−0.004 (2)
C70.024 (2)0.019 (2)0.022 (2)0.0019 (17)0.0094 (18)0.0021 (16)
C80.023 (2)0.021 (2)0.021 (2)−0.0050 (16)0.0088 (18)−0.0013 (16)
N10.032 (2)0.0186 (17)0.0189 (17)−0.0044 (15)0.0083 (16)0.0033 (14)
N20.029 (2)0.0235 (19)0.030 (2)−0.0030 (16)0.0062 (17)0.0079 (16)
N30.031 (2)0.0223 (19)0.0235 (19)−0.0053 (15)0.0041 (17)0.0025 (14)
N40.0271 (18)0.0168 (17)0.0210 (18)−0.0020 (14)0.0088 (15)0.0001 (13)
O10.0390 (18)0.0226 (15)0.0179 (14)0.0056 (13)0.0101 (13)−0.0029 (12)
O20.048 (2)0.0232 (16)0.0191 (15)0.0050 (14)0.0100 (15)−0.0004 (12)
O1W0.0385 (18)0.0309 (17)0.0284 (17)0.0003 (15)0.0150 (15)−0.0012 (14)
Geometric parameters (Å, º) top
Zn1—O1i2.000 (3)C3—H30.9300
Zn1—O12.000 (3)C4—C51.369 (6)
Zn1—N4ii2.008 (3)C4—H40.9300
Zn1—N4iii2.008 (3)C5—C61.387 (6)
Zn2—N12.072 (3)C5—H50.9300
Zn2—N1iv2.072 (3)C6—C71.389 (6)
Zn2—O2iv2.082 (3)C6—H60.9300
Zn2—O22.082 (3)C7—C81.491 (5)
Zn2—O1Wiv2.193 (3)C8—O21.240 (5)
Zn2—O1W2.193 (3)C8—O11.281 (5)
C1—N11.321 (5)N1—N21.345 (5)
C1—N41.343 (5)N2—N31.300 (4)
C1—C21.484 (5)N3—N41.353 (5)
C2—C31.390 (5)N4—Zn1v2.008 (3)
C2—C71.411 (5)O1W—H1W0.8200
C3—C41.389 (6)O1W—H2W0.7851
O1i—Zn1—O197.27 (17)C2—C3—H3119.5
O1i—Zn1—N4ii124.90 (13)C5—C4—C3119.8 (4)
O1—Zn1—N4ii105.93 (12)C5—C4—H4120.1
O1i—Zn1—N4iii105.93 (12)C3—C4—H4120.1
O1—Zn1—N4iii124.90 (13)C4—C5—C6120.2 (4)
N4ii—Zn1—N4iii100.34 (19)C4—C5—H5119.9
N1—Zn2—N1iv180.000 (1)C6—C5—H5119.9
N1—Zn2—O2iv93.81 (13)C5—C6—C7121.1 (4)
N1iv—Zn2—O2iv86.19 (13)C5—C6—H6119.4
N1—Zn2—O286.19 (13)C7—C6—H6119.4
N1iv—Zn2—O293.81 (13)C6—C7—C2118.7 (4)
O2iv—Zn2—O2180.000 (1)C6—C7—C8117.4 (4)
N1—Zn2—O1Wiv90.11 (13)C2—C7—C8123.9 (3)
N1iv—Zn2—O1Wiv89.89 (13)O2—C8—O1121.1 (4)
O2iv—Zn2—O1Wiv92.66 (12)O2—C8—C7122.1 (4)
O2—Zn2—O1Wiv87.34 (12)O1—C8—C7116.8 (4)
N1—Zn2—O1W89.89 (13)C1—N1—N2106.9 (3)
N1iv—Zn2—O1W90.11 (13)C1—N1—Zn2132.8 (3)
O2iv—Zn2—O1W87.34 (12)N2—N1—Zn2120.0 (3)
O2—Zn2—O1W92.66 (12)N3—N2—N1109.3 (3)
O1Wiv—Zn2—O1W180.000 (1)N2—N3—N4108.4 (3)
N1—C1—N4109.2 (4)C1—N4—N3106.3 (3)
N1—C1—C2129.5 (4)C1—N4—Zn1v131.8 (3)
N4—C1—C2121.1 (3)N3—N4—Zn1v121.1 (3)
C3—C2—C7119.2 (4)C8—O1—Zn1108.4 (3)
C3—C2—C1115.9 (4)C8—O2—Zn2145.6 (3)
C7—C2—C1124.5 (4)Zn2—O1W—H1W109.5
C4—C3—C2120.9 (4)Zn2—O1W—H2W121.0
C4—C3—H3119.5H1W—O1W—H2W95.2
Symmetry codes: (i) −x+2, y, −z+1/2; (ii) −x+2, y−1, −z+1/2; (iii) x, y−1, z; (iv) −x+2, −y, −z+1; (v) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O1vi0.822.082.804 (4)147
O1W—H2W···N3vii0.792.252.976 (5)155
Symmetry codes: (vi) x, −y, z+1/2; (vii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula[Zn(C8H4N4O2)(H2O)]
Mr271.56
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)19.696 (8), 7.1340 (18), 14.932 (6)
β (°) 114.39 (2)
V (Å3)1910.9 (12)
Z8
Radiation typeMo Kα
µ (mm−1)2.57
Crystal size (mm)0.07 × 0.07 × 0.06
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.835, 0.860
No. of measured, independent and
observed [I > 2σ(I)] reflections		9320, 2173, 1623
Rint0.085
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.112, 1.08
No. of reflections2173
No. of parameters147
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.63, −0.60

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O1i0.822.082.804 (4)147.2
O1W—H2W···N3ii0.792.252.976 (5)155.0
Symmetry codes: (i) x, −y, z+1/2; (ii) −x+2, −y+1, −z+1.
 

Acknowledgements

This work was supported by a Start-up Grant from Southeast University to ZRQ.

References

First citationDunica, J. V., Pierce, M. E. & Santella, J. B. III (1991). J. Org. Chem. 56, 2395–2400.  Google Scholar
 First citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.  Google Scholar
 First citationHu, B., Xu, X.-B., Li, Y.-X. & Ye, H.-Y. (2007). Acta Cryst. E63, m2698.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationLi, J.-T., Tao, J., Huang, R.-B. & Zhang, L.-S. (2005). Acta Cryst. E61, m984–m985.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWang, X.-S., Tang, Y.-Z., Huang, X.-F., Qu, Z.-R., Che, C.-M., Chan, C. W. H. & Xiong, R.-G. (2005). Inorg. Chem. 44, 5278–5285.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationWittenberger, S. J. & Donner, B. G. (1993). J. Org. Chem. 58, 4139–4141.  CrossRef CAS Web of Science Google Scholar
 First citationXiong, R.-G., Xue, X., Zhao, H., You, X.-Z., Abrahams, B. F. & Xue, Z.-L. (2002). Angew. Chem. Int. Ed. 41, 3800–3803.  Web of Science CrossRef CAS Google Scholar
 First citationXue, X., Wang, X.-S., Wang, L.-Z., Xiong, R.-G., Abrahams, B. F., You, X.-Z., Xue, Z.-L. & Che, C.-M. (2002). Inorg. Chem. 41, 3800–3803.  Web of Science CSD CrossRef Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 6| June 2008| Page m808
doi:10.1107/S1600536808013688
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