Diaqua­bis­{3-[4-(1H-imidazol-1-yl)phenyl]-5-(pyridin-2-yl-κN)-1H-1,2,4-triazol-1-ido-κN1}zinc

Wang, Y.-S.; Qiu, G.-M.; Wang, C.-J.

doi:10.1107/S1600536812035428

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Pages m1182-m1183

doi:10.1107/S1600536812035428

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Diaquabis{3-[4-(1H-imidazol-1-yl)phenyl]-5-(pyridin-2-yl-κN)-1H-1,2,4-triazol-1-ido-κN¹}zinc

You-Song Wang,^a Guang-Mei Qiu ^a and Cui-Juan Wang ^a ^*

^aDepartment of Chemistry and Chemical Engineering, College of Life Science and Bioengineering, SouthWest JiaoTong University, Chengdu, Sichuan 610031, People's Republic of China
^*Correspondence e-mail: ejuan6046@sina.com

(Received 22 June 2012; accepted 10 August 2012; online 23 August 2012)

The centrosymmetric molecule of the title compound, [Zn(C₁₆H₁₁N₆)₂(H₂O)₂], contains one Zn²⁺ ion located on a center of symmetry, two 3-[4-(1H-imidazol-1-yl)phenyl]-5-(pyridin-2-yl)-1H-1,2,4-triazol-1-ide (Ippyt) ligands and two coordinating water molecules. The Zn^II ion is six-coordinated in a distorted octahedral coordination geometry by four N atoms from two Ippyt ligands and by two O atoms from two water molecules. Adjacent units are interconnected though O—H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For similar structures, see: Braga et al. (2005 ); Lin et al. (2010 ); Faulmann et al. (1990 ); Han et al. (2005 ); Xue et al. (2009 ).

Experimental

Crystal data

[Zn(C₁₆H₁₁N₆)₂(H₂O)₂]
M_r = 676.04
Monoclinic, P 2₁ /c
a = 12.6481 (9) Å
b = 11.6659 (6) Å
c = 10.4922 (7) Å
β = 105.891 (7)°
V = 1488.98 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.88 mm⁻¹
T = 293 K
0.03 × 0.03 × 0.02 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.974, T_max = 0.983
4938 measured reflections
2626 independent reflections
1724 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.109
S = 1.02
2626 reflections
214 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N6ⁱ	0.82	2.03	2.842 (4)	174
O1—H1B⋯N4ⁱⁱ	0.85	2.07	2.868 (4)	157
Symmetry codes: (i) -x+2, -y, -z+2; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812035428/br2206sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812035428/br2206Isup2.hkl

checkCIF report

Comment top

The rational design and syntheses of metal-organic frameworks have been of increasing interest in the crystal engineering of coordination polymers owing to their ability to provide diverse assemblies with fascinating topological structures and material properties ( Han et al., 2005; Xue et al.,2009). The centrosymmetric unit of the title compound contains one Zn²⁺ion, two Ippyt ligands and two coordination water molecules. For a similar structure, see: Braga et al. (2005); Lin et al. (2010); Faulmann et al. (1990). Every Zn^II ion is six-coordinated in a distorted octahedral coordination geometry by four N atoms from two Ippyt ligands and by two O atoms from two coordination water molecules (Fig. 1). There are two kinds of hydrogen bonding interactions which are between the coordinated waters and the triazolyl nitrogen atoms, and between the coordinated waters and the imidazolyl nitrogen atoms, respectively. However, the construct units are connected by the hydrogen bonding interactions between oxygen/ imidazolyl nitrogen atoms and imidazolyl nitrogen/ oxygen atoms from adjacent units respectively. Thus, infinite one-dimensional ring-shaped chains are formed. And then N3 and N3' are further involved in forming another hydrogen bonding interactions with other neighbouring water oxygen atoms and thus connect the 1D supramolecular chains together to form the two-dimensional supramolecular architecture in the a,c plane. And finally the structures are interlinked alternately by different hydrogen bonding interactions and finally result in the three-dimensional supramolecular network architectures.(Fig.2).

Related literature top

For similar structures, see: Braga et al. (2005); Lin et al. (2010); Faulmann et al. (1990); Han et al. (2005); Xue et al. (2009).

Experimental top

A mixture of Zn(NO₃)₂.6H₂O (0.02 mmol), Ippyt (0.02 mmol), H2O (8 ml) was sealed in 25ml Teflon-lined stainless steel reactor, which was heated to 413 K for 5d and was subsequently cooled slowly to room temperature. Colourless block-shaped crystals were collected in 47% yield based on Zn.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The coordination environment of Zn^II atom in the title compound.
	Fig. 2. The 3D supermolecule network of the title compound. Dashed lines denote hydrogen bonds.

Diaquabis{3-[4-(1H-imidazol-1-yl)phenyl]-5-(pyridin-2-yl- κN)-1H-1,2,4-triazol-1-ido-κN¹}zinc top

Crystal data top

[Zn(C₁₆H₁₁N₆)₂(H₂O)₂]	F(000) = 700
M_r = 676.04	D_x = 1.512 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1141 reflections
a = 12.6481 (9) Å	θ = 2.4–28.3°
b = 11.6659 (6) Å	µ = 0.88 mm⁻¹
c = 10.4922 (7) Å	T = 293 K
β = 105.891 (7)°	Block, colourless
V = 1488.98 (16) Å³	0.03 × 0.03 × 0.02 mm
Z = 2

Data collection top

Bruker SMART diffractometer	2626 independent reflections
Radiation source: fine-focus sealed tube	1724 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→8
T_min = 0.974, T_max = 0.983	k = −12→13
4938 measured reflections	l = −8→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0332P)²] where P = (F_o² + 2F_c²)/3
S = 1.02
2626 reflections	Δρ_max = 0.23 e Å⁻³
214 parameters	Δρ_min = −0.29 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

[Zn(C₁₆H₁₁N₆)₂(H₂O)₂]	V = 1488.98 (16) Å³
M_r = 676.04	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.6481 (9) Å	µ = 0.88 mm⁻¹
b = 11.6659 (6) Å	T = 293 K
c = 10.4922 (7) Å	0.03 × 0.03 × 0.02 mm
β = 105.891 (7)°

Data collection top

Bruker SMART diffractometer	2626 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1724 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.983	R_int = 0.048
4938 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	214 parameters
wR(F²) = 0.109	H-atom parameters constrained
S = 1.02	Δρ_max = 0.23 e Å⁻³
2626 reflections	Δρ_min = −0.29 e Å⁻³

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	0.0000	0.5000	0.0451 (2)
N1	0.4454 (2)	0.1728 (2)	0.4816 (3)	0.0390 (8)
N2	0.6022 (2)	0.0728 (2)	0.6718 (3)	0.0391 (8)
N3	0.6852 (2)	0.0414 (3)	0.7797 (3)	0.0441 (8)
N4	0.6357 (2)	0.2248 (2)	0.8079 (3)	0.0385 (8)
N5	1.0281 (2)	0.1265 (3)	1.3567 (3)	0.0553 (9)
N6	1.1782 (3)	0.0806 (3)	1.5144 (4)	0.0726 (12)
O1	0.62155 (17)	0.04131 (19)	0.3861 (3)	0.0481 (7)
H1B	0.6317	0.1134	0.3870	0.058*
H1	0.6799	0.0087	0.4200	0.072*
C1	0.3757 (3)	0.2195 (3)	0.3764 (4)	0.0469 (10)
H1A	0.3432	0.1729	0.3045	0.056*
C2	0.3496 (3)	0.3348 (3)	0.3698 (4)	0.0516 (11)
H2	0.3024	0.3661	0.2938	0.062*
C3	0.3952 (3)	0.4012 (3)	0.4776 (4)	0.0545 (11)
H3	0.3769	0.4784	0.4767	0.065*
C4	0.4682 (3)	0.3549 (3)	0.5884 (4)	0.0474 (10)
H4	0.4994	0.4000	0.6623	0.057*
C5	0.4938 (2)	0.2399 (3)	0.5865 (4)	0.0344 (8)
C6	0.5757 (3)	0.1811 (3)	0.6919 (4)	0.0347 (8)
C7	0.7019 (3)	0.1340 (3)	0.8583 (4)	0.0378 (9)
C8	0.7859 (3)	0.1342 (3)	0.9879 (4)	0.0393 (9)
C9	0.7952 (3)	0.2227 (3)	1.0774 (4)	0.0468 (10)
H9	0.7472	0.2846	1.0566	0.056*
C10	0.8756 (3)	0.2204 (3)	1.1987 (4)	0.0510 (11)
H10	0.8815	0.2811	1.2578	0.061*
C11	0.9465 (3)	0.1283 (3)	1.2313 (4)	0.0464 (10)
C12	0.9361 (3)	0.0383 (4)	1.1451 (5)	0.0595 (12)
H12	0.9823	−0.0249	1.1676	0.071*
C13	0.8562 (3)	0.0414 (3)	1.0237 (4)	0.0559 (11)
H13	0.8500	−0.0199	0.9655	0.067*
C14	1.0221 (4)	0.1771 (6)	1.4698 (5)	0.113 (2)
H14	0.9652	0.2232	1.4806	0.136*
C15	1.1136 (4)	0.1485 (5)	1.5641 (5)	0.114 (2)
H15	1.1299	0.1725	1.6519	0.137*
C16	1.1249 (3)	0.0693 (4)	1.3884 (5)	0.0675 (13)
H16	1.1507	0.0269	1.3280	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0514 (4)	0.0329 (3)	0.0373 (4)	0.0044 (3)	−0.0112 (3)	−0.0042 (4)
N1	0.0353 (16)	0.0368 (18)	0.037 (2)	0.0012 (14)	−0.0030 (14)	0.0003 (16)
N2	0.0400 (17)	0.0332 (17)	0.0352 (19)	0.0010 (13)	−0.0049 (14)	−0.0039 (15)
N3	0.0469 (18)	0.0380 (18)	0.036 (2)	0.0023 (14)	−0.0069 (15)	−0.0009 (17)
N4	0.0367 (16)	0.0354 (17)	0.0371 (19)	0.0015 (13)	−0.0005 (14)	−0.0029 (16)
N5	0.0367 (18)	0.082 (2)	0.040 (2)	0.0157 (17)	−0.0026 (15)	−0.002 (2)
N6	0.049 (2)	0.097 (3)	0.056 (3)	0.018 (2)	−0.0124 (19)	0.001 (3)
O1	0.0452 (14)	0.0400 (14)	0.0496 (18)	0.0068 (11)	−0.0032 (12)	0.0066 (14)
C1	0.048 (2)	0.048 (3)	0.033 (2)	0.0015 (18)	−0.0066 (18)	−0.001 (2)
C2	0.052 (2)	0.045 (2)	0.045 (3)	0.0087 (19)	−0.008 (2)	0.005 (2)
C3	0.059 (3)	0.038 (2)	0.056 (3)	0.0133 (19)	−0.002 (2)	0.000 (2)
C4	0.052 (2)	0.037 (2)	0.043 (3)	0.0054 (18)	−0.0035 (19)	−0.008 (2)
C5	0.0328 (19)	0.034 (2)	0.033 (2)	0.0002 (15)	0.0020 (16)	0.0004 (19)
C6	0.038 (2)	0.033 (2)	0.032 (2)	−0.0027 (16)	0.0065 (16)	−0.0031 (18)
C7	0.035 (2)	0.040 (2)	0.034 (2)	−0.0052 (16)	0.0028 (16)	−0.001 (2)
C8	0.034 (2)	0.042 (2)	0.036 (2)	0.0027 (16)	0.0006 (17)	0.002 (2)
C9	0.044 (2)	0.050 (2)	0.041 (3)	0.0092 (18)	0.0016 (18)	−0.003 (2)
C10	0.047 (2)	0.060 (3)	0.039 (2)	0.008 (2)	−0.0003 (19)	−0.015 (2)
C11	0.040 (2)	0.057 (3)	0.035 (2)	0.0064 (19)	−0.0021 (17)	0.001 (2)
C12	0.053 (3)	0.057 (3)	0.055 (3)	0.020 (2)	−0.007 (2)	−0.003 (3)
C13	0.056 (2)	0.050 (2)	0.051 (3)	0.009 (2)	−0.003 (2)	−0.010 (2)
C14	0.078 (4)	0.202 (7)	0.045 (3)	0.071 (4)	−0.008 (3)	−0.024 (4)
C15	0.074 (4)	0.209 (7)	0.041 (3)	0.057 (4)	−0.015 (3)	−0.018 (4)
C16	0.054 (3)	0.075 (3)	0.059 (3)	0.017 (2)	−0.009 (2)	−0.005 (3)

Geometric parameters (Å, º) top

Zn1—N2ⁱ	2.090 (3)	C2—C3	1.362 (5)
Zn1—N2	2.090 (3)	C2—H2	0.9300
Zn1—N1	2.123 (3)	C3—C4	1.381 (5)
Zn1—N1ⁱ	2.123 (3)	C3—H3	0.9300
Zn1—O1ⁱ	2.243 (2)	C4—C5	1.381 (4)
Zn1—O1	2.243 (2)	C4—H4	0.9300
N1—C1	1.326 (4)	C5—C6	1.463 (5)
N1—C5	1.353 (4)	C7—C8	1.479 (5)
N2—C6	1.339 (4)	C8—C9	1.378 (5)
N2—N3	1.366 (4)	C8—C13	1.385 (5)
N3—C7	1.340 (4)	C9—C10	1.396 (5)
N4—C6	1.346 (4)	C9—H9	0.9300
N4—C7	1.365 (4)	C10—C11	1.381 (5)
N5—C14	1.345 (6)	C10—H10	0.9300
N5—C16	1.353 (5)	C11—C12	1.368 (5)
N5—C11	1.433 (5)	C12—C13	1.393 (5)
N6—C16	1.316 (6)	C12—H12	0.9300
N6—C15	1.343 (6)	C13—H13	0.9300
O1—H1B	0.8500	C14—C15	1.342 (6)
O1—H1	0.8199	C14—H14	0.9300
C1—C2	1.382 (5)	C15—H15	0.9300
C1—H1A	0.9300	C16—H16	0.9300

N2ⁱ—Zn1—N2	180.0	C3—C4—C5	118.2 (4)
N2ⁱ—Zn1—N1	101.45 (11)	C3—C4—H4	120.9
N2—Zn1—N1	78.55 (11)	C5—C4—H4	120.9
N2ⁱ—Zn1—N1ⁱ	78.55 (11)	N1—C5—C4	121.2 (3)
N2—Zn1—N1ⁱ	101.45 (11)	N1—C5—C6	114.4 (3)
N1—Zn1—N1ⁱ	180.0	C4—C5—C6	124.4 (3)
N2ⁱ—Zn1—O1ⁱ	91.13 (10)	N2—C6—N4	113.4 (3)
N2—Zn1—O1ⁱ	88.87 (10)	N2—C6—C5	118.7 (3)
N1—Zn1—O1ⁱ	89.95 (10)	N4—C6—C5	127.8 (3)
N1ⁱ—Zn1—O1ⁱ	90.05 (10)	N3—C7—N4	114.3 (3)
N2ⁱ—Zn1—O1	88.87 (10)	N3—C7—C8	121.3 (3)
N2—Zn1—O1	91.13 (10)	N4—C7—C8	124.5 (3)
N1—Zn1—O1	90.05 (10)	C9—C8—C13	118.2 (3)
N1ⁱ—Zn1—O1	89.95 (10)	C9—C8—C7	122.2 (3)
O1ⁱ—Zn1—O1	180.0	C13—C8—C7	119.6 (4)
C1—N1—C5	119.3 (3)	C8—C9—C10	120.8 (3)
C1—N1—Zn1	126.3 (3)	C8—C9—H9	119.6
C5—N1—Zn1	114.3 (2)	C10—C9—H9	119.6
C6—N2—N3	107.0 (3)	C11—C10—C9	120.1 (4)
C6—N2—Zn1	113.4 (2)	C11—C10—H10	119.9
N3—N2—Zn1	139.4 (2)	C9—C10—H10	119.9
C7—N3—N2	104.4 (3)	C12—C11—C10	119.7 (4)
C6—N4—C7	101.0 (3)	C12—C11—N5	120.7 (3)
C14—N5—C16	105.4 (4)	C10—C11—N5	119.6 (4)
C14—N5—C11	127.1 (3)	C11—C12—C13	119.9 (4)
C16—N5—C11	127.4 (4)	C11—C12—H12	120.0
C16—N6—C15	104.5 (4)	C13—C12—H12	120.0
Zn1—O1—H1B	109.3	C8—C13—C12	121.3 (4)
Zn1—O1—H1	109.7	C8—C13—H13	119.4
H1B—O1—H1	109.8	C12—C13—H13	119.4
N1—C1—C2	122.5 (4)	C15—C14—N5	107.2 (4)
N1—C1—H1A	118.8	C15—C14—H14	126.4
C2—C1—H1A	118.8	N5—C14—H14	126.4
C3—C2—C1	118.1 (4)	C14—C15—N6	110.7 (5)
C3—C2—H2	121.0	C14—C15—H15	124.6
C1—C2—H2	121.0	N6—C15—H15	124.6
C2—C3—C4	120.7 (3)	N6—C16—N5	112.2 (4)
C2—C3—H3	119.7	N6—C16—H16	123.9
C4—C3—H3	119.7	N5—C16—H16	123.9

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
O1—H1···N6ⁱⁱ	0.82	2.03	2.842 (4)	174
O1—H1B···N4ⁱⁱⁱ	0.85	2.07	2.868 (4)	157

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₆H₁₁N₆)₂(H₂O)₂]
M_r	676.04
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.6481 (9), 11.6659 (6), 10.4922 (7)
β (°)	105.891 (7)
V (Å³)	1488.98 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.88
Crystal size (mm)	0.03 × 0.03 × 0.02

Data collection
Diffractometer	Bruker SMART diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.974, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	4938, 2626, 1724
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.109, 1.02
No. of reflections	2626
No. of parameters	214
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.29

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N6ⁱ	0.82	2.03	2.842 (4)	174.1
O1—H1B···N4ⁱⁱ	0.85	2.07	2.868 (4)	156.7

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

Acknowledgements

This work was supported by the Fundamental Research Funds for the Central Universities, P. R. China (No. SWJTU12CX048).

References

Braga, D., Polito, M., Giaffreda, S. L. & Grepioni, F. (2005). Discuss. Faraday Soc. pp. 2766–73. Google Scholar
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