Diaqua­bis{2-[5-(2-pyrid­yl)-2H-tetra­zol-2-yl]acetato-κ2N4,N5}zinc(II)

Wang, B.

doi:10.1107/S1600536809023940

metal-organic compounds

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Volume 65| Part 7| July 2009| Page m831

doi:10.1107/S1600536809023940

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Diaquabis{2-[5-(2-pyridyl)-2H-tetrazol-2-yl]acetato-κ²N⁴,N⁵}zinc(II)

Bo Wang ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: fudavid88@yahoo.com.cn

(Received 18 June 2009; accepted 22 June 2009; online 27 June 2009)

The title compound, [Zn(C₈H₆N₅O₂)₂(H₂O)₂], was synthesized by hydrothermal reaction of ZnBr₂ with 2-[5-(2-pyridyl)-2H-tetrazol-2-yl]acetic acid. The Zn^II atom lies on an inversion center in a distorted octahedral environment with two planar trans-related N,N′-chelating 2-[5-(2-pyridyl)-2H-tetrazol-2-yl]acetic acid ligands in the equatorial plane and two water molecules in the axial positions. In the crystal, O—H⋯O hydrogen bonds generate an infinite three-dimensional network.

Related literature

For the chemisty of tetrazoles, see: Fu et al. (2008 ); Dai & Fu (2008 ); Wang et al. (2005 ); Wen (2008 ); Wittenberger & Donner (1993 ).

Experimental

Crystal data

[Zn(C₈H₆N₅O₂)₂(H₂O)₂]
M_r = 509.76
Monoclinic, P 2₁ /c
a = 7.6407 (15) Å
b = 8.2583 (17) Å
c = 15.155 (3) Å
β = 97.17 (3)°
V = 948.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.36 mm⁻¹
T = 298 K
0.35 × 0.25 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.762, T_max = 0.841 (expected range = 0.690–0.762)
9600 measured reflections
2177 independent reflections
1984 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.075
S = 1.11
2177 reflections
151 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WB⋯O1ⁱ	0.85	1.85	2.6891 (19)	172
O1W—H1WA⋯O2ⁱⁱ	0.85	1.80	2.6365 (17)	169
Symmetry codes: (i) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023940/dn2467sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023940/dn2467Isup2.hkl

checkCIF report

Comment top

The tetrazole functional group has found a wide range of applications in coordination chemistry as ligands, in medicinal chemistry as a metabolically stable surrogate for a carboxylic acid group, and in materials science as high density energy materials(Wang et al., 2005; Fu et al., 2008; Wittenberger et al.,1993). We report here the crystal structure of the title compound, Bis[2-(5-(pyridin-2-yl)-2H-tetrazol-2-yl)acetic-K²N¹,N²]Zinc(II).

In the title compound, the Zn^II atom lies on an inversion center. The distorted octahedral Zn^II environment contains two planar trans-related N,N-chelating 2-(5-(pyridin-2-yl)-2H-tetrazol-2-yl)acetic acid ligands in the equatorial plane and two water ligands in the axial positions. The pyridine and tetrazole rings are nearly coplanar and only twisted from each other by a dihedral angle of 7.06 ( 1 )°. The geometric parameters of the tetrazole rings are comparable to those in related molecules (Wittenberger et al., 1993; Dai & Fu 2008; Wen 2008).

The O atoms from water molecules are involved in intermolecular O—H···O hydrogen bonds building up an infinite three-dimensional network (Table 1 and Fig.2).

Related literature top

For the chemisty of tetrazoles, see: Fu et al. (2008); Dai & Fu (2008); Wang et al. (2005); Wen (2008); Wittenberger & Donner (1993).

Experimental top

A mixture of 2-(5-(pyridin-2-yl)-2H-tetrazol-2-yl)acetic acid (0.2 mmol), ZnBr₂ (0.4 mmol), distilled water (1 ml) and a few drops of ethanol sealed in a glass tube was maintained at 110 °C. Colorless block crystals suitable for X-ray analysis were obtained after 3 days.

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: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.[Symmetry codes: (i) -x+1, -y+1, -z+1]
	Fig. 2. The crystal packing of the title compound viewed along the a axis showing the three dimensionnal hydrogen bondings network (dashed line). Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

Diaquabis{2-[5-(2-pyridyl)-2H-tetrazol-2-yl]acetato- κ²N⁴,N⁵}zinc(II) top

Crystal data top

[Zn(C₈H₆N₅O₂)₂(H₂O)₂]	F(000) = 520
M_r = 509.76	D_x = 1.784 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1984 reflections
a = 7.6407 (15) Å	θ = 3.6–27.5°
b = 8.2583 (17) Å	µ = 1.36 mm⁻¹
c = 15.155 (3) Å	T = 298 K
β = 97.17 (3)°	Block, colorless
V = 948.8 (3) Å³	0.35 × 0.25 × 0.20 mm
Z = 2

Data collection top

Rigaku Mercury2 diffractometer	2177 independent reflections
Radiation source: fine-focus sealed tube	1984 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.6°
CCD profile fitting scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
T_min = 0.762, T_max = 0.841	l = −19→19
9600 measured reflections

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0393P)² + 0.3221P] where P = (F_o² + 2F_c²)/3
2177 reflections	(Δ/σ)_max < 0.001
151 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Zn(C₈H₆N₅O₂)₂(H₂O)₂]	V = 948.8 (3) Å³
M_r = 509.76	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.6407 (15) Å	µ = 1.36 mm⁻¹
b = 8.2583 (17) Å	T = 298 K
c = 15.155 (3) Å	0.35 × 0.25 × 0.20 mm
β = 97.17 (3)°

Data collection top

Rigaku Mercury2 diffractometer	2177 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1984 reflections with I > 2σ(I)
T_min = 0.762, T_max = 0.841	R_int = 0.031
9600 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.11	Δρ_max = 0.25 e Å⁻³
2177 reflections	Δρ_min = −0.41 e Å⁻³
151 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Zn1	0.5000	0.5000	0.5000	0.02160 (10)
N1	0.32018 (18)	0.61053 (17)	0.39557 (9)	0.0230 (3)
O1W	0.72023 (15)	0.59206 (14)	0.44676 (8)	0.0267 (3)
H1WA	0.7564	0.5199	0.4135	0.040*
H1WB	0.8013	0.6233	0.4865	0.040*
N5	0.45085 (17)	0.73160 (16)	0.55431 (9)	0.0212 (3)
O1	−0.0465 (2)	0.79027 (18)	0.07872 (9)	0.0417 (3)
N2	0.22867 (19)	0.57379 (18)	0.31894 (9)	0.0253 (3)
O2	0.16960 (18)	0.89846 (16)	0.17318 (8)	0.0353 (3)
N3	0.11283 (18)	0.68988 (17)	0.30393 (9)	0.0238 (3)
C5	0.3275 (2)	0.82286 (19)	0.50739 (10)	0.0211 (3)
C6	0.2532 (2)	0.74873 (19)	0.42345 (10)	0.0213 (3)
N4	0.12076 (19)	0.80232 (17)	0.36653 (9)	0.0260 (3)
C1	0.5300 (2)	0.7902 (2)	0.63096 (11)	0.0275 (4)
H1	0.6149	0.7271	0.6643	0.033*
C4	0.2795 (2)	0.9734 (2)	0.53507 (12)	0.0281 (4)
H4	0.1925	1.0336	0.5013	0.034*
C2	0.4912 (3)	0.9404 (2)	0.66288 (12)	0.0320 (4)
H2	0.5501	0.9787	0.7162	0.038*
C3	0.3640 (3)	1.0324 (2)	0.61438 (13)	0.0330 (4)
H3	0.3349	1.1339	0.6348	0.040*
C7	−0.0122 (2)	0.6946 (2)	0.22339 (11)	0.0303 (4)
H7A	−0.1255	0.7307	0.2384	0.036*
H7B	−0.0273	0.5858	0.1996	0.036*
C8	0.0445 (2)	0.8059 (2)	0.15154 (11)	0.0258 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02190 (16)	0.02041 (15)	0.02109 (15)	0.00495 (9)	−0.00280 (10)	−0.00076 (9)
N1	0.0233 (7)	0.0239 (7)	0.0206 (6)	0.0030 (5)	−0.0022 (5)	0.0012 (5)
O1W	0.0250 (6)	0.0283 (6)	0.0263 (6)	0.0004 (5)	0.0008 (5)	−0.0052 (5)
N5	0.0203 (6)	0.0205 (6)	0.0221 (7)	0.0006 (5)	−0.0002 (5)	0.0001 (5)
O1	0.0499 (8)	0.0481 (9)	0.0238 (6)	0.0109 (7)	−0.0081 (6)	0.0047 (6)
N2	0.0269 (7)	0.0258 (7)	0.0213 (7)	0.0009 (6)	−0.0041 (5)	0.0027 (5)
O2	0.0390 (7)	0.0371 (7)	0.0304 (7)	−0.0054 (6)	0.0071 (5)	0.0062 (6)
N3	0.0234 (7)	0.0250 (7)	0.0211 (7)	−0.0008 (5)	−0.0043 (5)	0.0048 (5)
C5	0.0198 (7)	0.0216 (7)	0.0217 (8)	−0.0003 (6)	0.0018 (6)	0.0029 (6)
C6	0.0211 (7)	0.0211 (7)	0.0214 (8)	0.0005 (6)	0.0012 (6)	0.0044 (6)
N4	0.0254 (7)	0.0257 (7)	0.0253 (7)	0.0031 (6)	−0.0031 (5)	0.0032 (6)
C1	0.0249 (8)	0.0301 (9)	0.0258 (8)	−0.0007 (7)	−0.0034 (7)	−0.0010 (7)
C4	0.0293 (9)	0.0231 (8)	0.0317 (9)	0.0049 (7)	0.0035 (7)	0.0030 (7)
C2	0.0362 (10)	0.0319 (9)	0.0270 (9)	−0.0047 (8)	0.0002 (7)	−0.0069 (7)
C3	0.0430 (11)	0.0229 (8)	0.0342 (10)	0.0004 (7)	0.0089 (8)	−0.0060 (7)
C7	0.0284 (9)	0.0334 (9)	0.0254 (8)	−0.0047 (7)	−0.0109 (7)	0.0067 (7)
C8	0.0292 (8)	0.0260 (8)	0.0217 (8)	0.0103 (7)	0.0012 (6)	0.0034 (6)

Geometric parameters (Å, º) top

Zn1—O1W	2.0974 (13)	N3—N4	1.324 (2)
Zn1—O1Wⁱ	2.0974 (13)	N3—C7	1.453 (2)
Zn1—N5	2.1340 (14)	C5—C4	1.377 (2)
Zn1—N5ⁱ	2.1340 (14)	C5—C6	1.461 (2)
Zn1—N1ⁱ	2.1640 (14)	C6—N4	1.321 (2)
Zn1—N1	2.1640 (14)	C1—C2	1.377 (3)
N1—N2	1.3142 (19)	C1—H1	0.9300
N1—C6	1.341 (2)	C4—C3	1.380 (3)
O1W—H1WA	0.8486	C4—H4	0.9300
O1W—H1WB	0.8480	C2—C3	1.373 (3)
N5—C1	1.332 (2)	C2—H2	0.9300
N5—C5	1.339 (2)	C3—H3	0.9300
O1—C8	1.235 (2)	C7—C8	1.529 (2)
N2—N3	1.305 (2)	C7—H7A	0.9700
O2—C8	1.236 (2)	C7—H7B	0.9700

O1W—Zn1—O1Wⁱ	180.0	N5—C5—C4	122.90 (15)
O1W—Zn1—N5	90.67 (5)	N5—C5—C6	113.44 (14)
O1Wⁱ—Zn1—N5	89.33 (5)	C4—C5—C6	123.65 (15)
O1W—Zn1—N5ⁱ	89.33 (5)	N4—C6—N1	111.77 (14)
O1Wⁱ—Zn1—N5ⁱ	90.67 (5)	N4—C6—C5	127.65 (15)
N5—Zn1—N5ⁱ	180.000 (1)	N1—C6—C5	120.58 (14)
O1W—Zn1—N1ⁱ	88.14 (5)	C6—N4—N3	101.29 (13)
O1Wⁱ—Zn1—N1ⁱ	91.86 (5)	N5—C1—C2	122.66 (16)
N5—Zn1—N1ⁱ	102.84 (5)	N5—C1—H1	118.7
N5ⁱ—Zn1—N1ⁱ	77.16 (5)	C2—C1—H1	118.7
O1W—Zn1—N1	91.86 (5)	C5—C4—C3	118.07 (17)
O1Wⁱ—Zn1—N1	88.14 (5)	C5—C4—H4	121.0
N5—Zn1—N1	77.16 (5)	C3—C4—H4	121.0
N5ⁱ—Zn1—N1	102.84 (5)	C3—C2—C1	118.66 (17)
N1ⁱ—Zn1—N1	180.0	C3—C2—H2	120.7
N2—N1—C6	107.04 (13)	C1—C2—H2	120.7
N2—N1—Zn1	140.18 (11)	C2—C3—C4	119.59 (17)
C6—N1—Zn1	111.18 (10)	C2—C3—H3	120.2
Zn1—O1W—H1WA	108.1	C4—C3—H3	120.2
Zn1—O1W—H1WB	112.8	N3—C7—C8	113.54 (14)
H1WA—O1W—H1WB	111.8	N3—C7—H7A	108.9
C1—N5—C5	118.12 (14)	C8—C7—H7A	108.9
C1—N5—Zn1	125.41 (11)	N3—C7—H7B	108.9
C5—N5—Zn1	116.46 (11)	C8—C7—H7B	108.9
N3—N2—N1	105.00 (13)	H7A—C7—H7B	107.7
N2—N3—N4	114.90 (13)	O1—C8—O2	129.21 (17)
N2—N3—C7	121.74 (15)	O1—C8—C7	113.30 (16)
N4—N3—C7	123.35 (14)	O2—C8—C7	117.48 (15)

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
O1W—H1WB···O1ⁱⁱ	0.85	1.85	2.6891 (19)	172
O1W—H1WA···O2ⁱⁱⁱ	0.85	1.80	2.6365 (17)	169

Symmetry codes: (ii) x+1, −y+3/2, z+1/2; (iii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₆N₅O₂)₂(H₂O)₂]
M_r	509.76
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.6407 (15), 8.2583 (17), 15.155 (3)
β (°)	97.17 (3)
V (Å³)	948.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.36
Crystal size (mm)	0.35 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.762, 0.841
No. of measured, independent and observed [I > 2σ(I)] reflections	9600, 2177, 1984
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.075, 1.11
No. of reflections	2177
No. of parameters	151
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.41

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···O1ⁱ	0.85	1.85	2.6891 (19)	171.8
O1W—H1WA···O2ⁱⁱ	0.85	1.80	2.6365 (17)	168.6

Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) −x+1, y−1/2, −z+1/2.

Acknowledgements

This work was supported by a start-up grant from Southeast University to Professor Ren-Gen Xiong.

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