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

Li, B.

doi:10.1107/S1600536813005916

metal-organic compounds

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Volume 69| Part 4| April 2013| Page m214

doi:10.1107/S1600536813005916

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

Bin Li ^a ^*

^aAdvanced Material Institute of Research, Department of Chemistry and Chemical Engineering, Qilu Normal University, Zhangqiu 250200, People's Republic of China
^*Correspondence e-mail: libin_qlnu@yahoo.com.cn

(Received 25 February 2013; accepted 1 March 2013; online 16 March 2013)

The asymmetric unit of the title compound, [Zn(C₁₈H₁₂N₅)₂(H₂O)₂], consists a Zn^II ion, located on an inversion center, a deprotonated 5-pyridin-2-yl-3-[4-(pyridin-4-yl)phenyl]-1H-1,2,4-triazol-1-ido ligand and a water molecule. The whole molecule is generated by inversion symmetry. The Zn^II ion has a distorted octahedral coordination geometry, defined by four N atoms from the two deprotonated organic ligands and two water O atoms. In the crystal, O—H⋯N hydrogen bonds link the molecules, forming a three-dimensional network.

Related literature

For background to coordination complexes, see: Zhang et al. (2012a ,b ); Fan et al. (2013 ).

Experimental

Crystal data

[Zn(C₁₈H₁₂N₅)₂(H₂O)₂]
M_r = 698.05
Monoclinic, P 2₁ /c
a = 13.214 (5) Å
b = 12.049 (5) Å
c = 9.825 (4) Å
β = 100.709 (3)°
V = 1537.0 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.85 mm⁻¹
T = 296 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.905, T_max = 0.935
7962 measured reflections
2718 independent reflections
1731 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.151
S = 1.00
2718 reflections
229 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1W⋯N3ⁱ	0.75 (6)	2.07 (6)	2.812 (5)	169 (6)
O1—H2W⋯N5ⁱⁱ	0.85 (6)	2.38 (6)	3.165 (7)	155 (6)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z-1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813005916/su2568sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813005916/su2568Isup2.hkl

checkCIF report

Comment top

The design and synthesis of coordination complexes has attracted upsurging research interest not only because of their appealing structural and topological novelty but also owing to their potential applications in gas storage, microelectronics, ion exchange, chemical separations, nonlinear optics and heterogeneous catalysis. Here, we report on the complex formed by a solvothermal reaction of 2-(3-(4-(pyridin-4- yl)phenyl)-1H-1,2,4-triazol-5-yl)pyridine with zinc(II) acetate.

The title compound, Fig. 1, possesses inversion symmetry, and consists of a zinc atom (located on the inversion center) coordinated to two symmetry related deprotonated 2-(3-(4-(pyridin-4- yl)phenyl)-1H-1,2,4-triazol-5-yl)pyridine ligands and two water molecules. The zinc atom, Zn1, has a distorted ZnN4O2 octahedral coordination geometry; completed by four N atoms of the ligand and two O atoms from the two water molecules. The Zn1—O1 distance is 2.301 (4) Å, and the Zn—N distances varying from 2.048 (3) - 2.134 (3) Å.

In the crystal, O-H···N hydrogen bonds link the molecules forming a three-dimensional network (Fig. 2 and Table 1).

Related literature top

For background to coordination complexes, see: Zhang et al. (2012a,b); Fan et al. (2013).

Experimental top

A mixture of 2-(3-(4-(pyridin-4- yl)phenyl)-1H-1,2,4-triazol-5-yl)pyridine (0.20 mmol, 0.060 g), zinc acetate dihydrate (0.20 mmol, 0.044 g) and NaOH (0.20 mmol, 0.008 g) in 12 mL H₂O was placed in a Teflon-lined stainless steel vessel and heated to 443 K for 3 days, followed by slow cooling (a descent rate of 10 K/h) to room temperature. Colourless block-like crystals suitable for X-ray diffraction analysis were obtained. Anal. Calc. for C₃₆H₂₈ZnN₁₀O₂: C 61.94, H 4.04, N 20.06%; Found: C 61.89, H 4.01, N 19.97%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atom-labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the b axis. Hydrogen bonds are shown as dashed cyan lines (see Table 1 for details; C-bound H atoms have been omitted for clarity).

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

Crystal data top

[Zn(C₁₈H₁₂N₅)₂(H₂O)₂]	F(000) = 720
M_r = 698.05	D_x = 1.508 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 985 reflections
a = 13.214 (5) Å	θ = 2.3–20.2°
b = 12.049 (5) Å	µ = 0.85 mm⁻¹
c = 9.825 (4) Å	T = 296 K
β = 100.709 (3)°	Block, colorless
V = 1537.0 (10) Å³	0.12 × 0.10 × 0.08 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	2718 independent reflections
Radiation source: fine-focus sealed tube	1731 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
phi and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→14
T_min = 0.905, T_max = 0.935	k = −14→14
7962 measured reflections	l = −11→9

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.035P)² + 1.3183P] where P = (F_o² + 2F_c²)/3
2718 reflections	(Δ/σ)_max = 0.001
229 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Zn(C₁₈H₁₂N₅)₂(H₂O)₂]	V = 1537.0 (10) Å³
M_r = 698.05	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.214 (5) Å	µ = 0.85 mm⁻¹
b = 12.049 (5) Å	T = 296 K
c = 9.825 (4) Å	0.12 × 0.10 × 0.08 mm
β = 100.709 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2718 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1731 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.935	R_int = 0.070
7962 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.65 e Å⁻³
2718 reflections	Δρ_min = −0.32 e Å⁻³
229 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
C1	0.3744 (3)	0.7926 (3)	−0.1269 (4)	0.0397 (11)
H1	0.3415	0.8410	−0.1946	0.048*
C2	0.3495 (4)	0.6829 (4)	−0.1378 (5)	0.0444 (12)
H2	0.3016	0.6568	−0.2124	0.053*
C3	0.3963 (4)	0.6118 (4)	−0.0371 (5)	0.0474 (13)
H3	0.3800	0.5366	−0.0424	0.057*
C4	0.4679 (4)	0.6519 (3)	0.0729 (5)	0.0412 (11)
H4	0.5001	0.6047	0.1426	0.049*
C5	0.4902 (3)	0.7630 (3)	0.0761 (4)	0.0317 (10)
C6	0.5671 (3)	0.8172 (3)	0.1839 (4)	0.0308 (10)
C7	0.6829 (3)	0.8610 (3)	0.3510 (4)	0.0360 (10)
C8	0.7641 (3)	0.8613 (4)	0.4753 (4)	0.0373 (11)
C9	0.8225 (4)	0.9560 (4)	0.5076 (5)	0.0619 (16)
H9	0.8083	1.0183	0.4514	0.074*
C10	0.9010 (4)	0.9603 (4)	0.6208 (6)	0.0636 (16)
H10	0.9395	1.0250	0.6386	0.076*
C11	0.9241 (4)	0.8705 (4)	0.7089 (5)	0.0459 (12)
C12	0.8626 (4)	0.7784 (4)	0.6780 (5)	0.0540 (14)
H12	0.8747	0.7172	0.7364	0.065*
C13	0.7839 (4)	0.7727 (4)	0.5648 (5)	0.0468 (12)
H13	0.7440	0.7088	0.5487	0.056*
C14	1.0114 (4)	0.8769 (4)	0.8265 (5)	0.0523 (13)
C15	1.0930 (5)	0.9456 (6)	0.8211 (7)	0.091 (2)
H15	1.0946	0.9868	0.7415	0.109*
C16	1.1734 (5)	0.9543 (6)	0.9339 (8)	0.091 (2)
H16	1.2270	1.0026	0.9262	0.109*
C17	1.1083 (6)	0.8258 (8)	1.0459 (7)	0.123 (3)
H17	1.1144	0.7771	1.1204	0.148*
C18	1.0230 (5)	0.8124 (7)	0.9395 (7)	0.112 (3)
H18	0.9739	0.7586	0.9472	0.134*
N1	0.4441 (3)	0.8336 (3)	−0.0228 (3)	0.0349 (9)
N2	0.5866 (3)	0.9241 (3)	0.1689 (4)	0.0390 (9)
N3	0.6254 (3)	0.7724 (3)	0.2965 (3)	0.0336 (9)
N4	0.6623 (3)	0.9535 (3)	0.2762 (4)	0.0406 (10)
N5	1.1795 (4)	0.8996 (5)	1.0499 (5)	0.0778 (15)
O1	0.3799 (3)	1.0467 (3)	0.1325 (4)	0.0501 (10)
Zn1	0.5000	1.0000	0.0000	0.0435 (3)
H1W	0.376 (5)	1.109 (5)	0.141 (6)	0.080*
H2W	0.328 (5)	1.006 (5)	0.139 (6)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.037 (3)	0.039 (2)	0.035 (3)	0.004 (2)	−0.014 (2)	0.003 (2)
C2	0.051 (3)	0.040 (3)	0.035 (3)	−0.009 (2)	−0.011 (2)	−0.006 (2)
C3	0.056 (3)	0.035 (2)	0.045 (3)	−0.007 (2)	−0.007 (3)	0.002 (2)
C4	0.048 (3)	0.033 (2)	0.036 (3)	0.001 (2)	−0.008 (2)	0.005 (2)
C5	0.035 (2)	0.032 (2)	0.026 (2)	0.0006 (18)	−0.001 (2)	−0.0002 (18)
C6	0.030 (2)	0.029 (2)	0.031 (2)	0.0004 (17)	−0.001 (2)	0.0008 (18)
C7	0.036 (3)	0.036 (2)	0.032 (3)	0.0013 (19)	−0.003 (2)	−0.002 (2)
C8	0.033 (3)	0.044 (3)	0.031 (2)	−0.002 (2)	−0.005 (2)	0.000 (2)
C9	0.068 (4)	0.041 (3)	0.060 (4)	−0.009 (3)	−0.031 (3)	0.010 (3)
C10	0.065 (4)	0.053 (3)	0.058 (4)	−0.016 (3)	−0.027 (3)	0.000 (3)
C11	0.039 (3)	0.061 (3)	0.032 (3)	−0.005 (2)	−0.009 (2)	0.005 (2)
C12	0.049 (3)	0.064 (3)	0.041 (3)	−0.006 (3)	−0.011 (3)	0.019 (3)
C13	0.046 (3)	0.048 (3)	0.040 (3)	−0.011 (2)	−0.008 (2)	0.009 (2)
C14	0.038 (3)	0.074 (4)	0.039 (3)	−0.009 (3)	−0.007 (3)	0.005 (3)
C15	0.076 (5)	0.097 (5)	0.081 (5)	−0.032 (4)	−0.033 (4)	0.014 (4)
C16	0.073 (5)	0.102 (5)	0.083 (5)	−0.026 (4)	−0.026 (4)	0.006 (4)
C17	0.092 (6)	0.197 (9)	0.059 (4)	−0.042 (6)	−0.039 (4)	0.053 (5)
C18	0.070 (5)	0.191 (8)	0.058 (4)	−0.042 (5)	−0.030 (4)	0.049 (5)
N1	0.039 (2)	0.0279 (18)	0.032 (2)	0.0037 (16)	−0.0103 (17)	0.0011 (15)
N2	0.041 (2)	0.034 (2)	0.034 (2)	−0.0006 (17)	−0.0135 (18)	−0.0007 (16)
N3	0.033 (2)	0.0334 (19)	0.029 (2)	0.0020 (15)	−0.0094 (17)	0.0007 (16)
N4	0.041 (2)	0.0330 (19)	0.038 (2)	0.0003 (17)	−0.0174 (19)	0.0022 (17)
N5	0.047 (3)	0.131 (5)	0.047 (3)	−0.003 (3)	−0.015 (2)	−0.003 (3)
O1	0.052 (2)	0.0376 (18)	0.054 (2)	−0.0033 (17)	−0.0082 (18)	−0.0060 (18)
Zn1	0.0506 (5)	0.0289 (4)	0.0399 (5)	−0.0042 (4)	−0.0204 (4)	0.0043 (3)

Geometric parameters (Å, º) top

C1—N1	1.338 (5)	C11—C14	1.475 (6)
C1—C2	1.361 (6)	C12—C13	1.375 (6)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.366 (6)	C13—H13	0.9300
C2—H2	0.9300	C14—C18	1.341 (7)
C3—C4	1.385 (6)	C14—C15	1.368 (8)
C3—H3	0.9300	C15—C16	1.389 (8)
C4—C5	1.370 (6)	C15—H15	0.9300
C4—H4	0.9300	C16—N5	1.306 (8)
C5—N1	1.348 (5)	C16—H16	0.9300
C5—C6	1.477 (5)	C17—N5	1.289 (8)
C6—N2	1.327 (5)	C17—C18	1.397 (8)
C6—N3	1.338 (5)	C17—H17	0.9300
C7—N4	1.335 (5)	C18—H18	0.9300
C7—N3	1.361 (5)	N1—Zn1	2.134 (3)
C7—C8	1.469 (6)	N2—N4	1.358 (5)
C8—C13	1.378 (6)	N2—Zn1	2.048 (3)
C8—C9	1.381 (6)	O1—Zn1	2.301 (4)
C9—C10	1.374 (7)	O1—H1W	0.75 (6)
C9—H9	0.9300	O1—H2W	0.85 (6)
C10—C11	1.384 (7)	Zn1—N2ⁱ	2.048 (3)
C10—H10	0.9300	Zn1—N1ⁱ	2.134 (3)
C11—C12	1.376 (6)	Zn1—O1ⁱ	2.301 (4)

N1—C1—C2	122.7 (4)	C15—C14—C11	120.6 (5)
N1—C1—H1	118.6	C16—C15—C14	120.5 (6)
C2—C1—H1	118.6	C16—C15—H15	119.8
C3—C2—C1	118.8 (4)	C14—C15—H15	119.8
C3—C2—H2	120.6	N5—C16—C15	124.9 (7)
C1—C2—H2	120.6	N5—C16—H16	117.6
C2—C3—C4	119.9 (4)	C15—C16—H16	117.6
C2—C3—H3	120.1	N5—C17—C18	125.8 (7)
C4—C3—H3	120.1	N5—C17—H17	117.1
C5—C4—C3	118.2 (4)	C18—C17—H17	117.1
C5—C4—H4	120.9	C14—C18—C17	120.3 (7)
C3—C4—H4	120.9	C14—C18—H18	119.9
N1—C5—C4	122.2 (4)	C17—C18—H18	119.8
N1—C5—C6	113.4 (3)	C1—N1—C5	118.2 (4)
C4—C5—C6	124.4 (4)	C1—N1—Zn1	127.1 (3)
N2—C6—N3	112.9 (3)	C5—N1—Zn1	114.6 (3)
N2—C6—C5	118.1 (3)	C6—N2—N4	107.3 (3)
N3—C6—C5	128.9 (4)	C6—N2—Zn1	115.6 (3)
N4—C7—N3	113.3 (4)	N4—N2—Zn1	137.1 (3)
N4—C7—C8	119.9 (4)	C6—N3—C7	101.7 (3)
N3—C7—C8	126.7 (4)	C7—N4—N2	104.8 (3)
C13—C8—C9	117.6 (4)	C17—N5—C16	113.3 (6)
C13—C8—C7	123.5 (4)	Zn1—O1—H1W	112 (5)
C9—C8—C7	119.0 (4)	Zn1—O1—H2W	123 (4)
C10—C9—C8	121.5 (5)	H1W—O1—H2W	119 (6)
C10—C9—H9	119.3	N2ⁱ—Zn1—N2	180.0
C8—C9—H9	119.3	N2ⁱ—Zn1—N1	101.80 (13)
C9—C10—C11	121.6 (5)	N2—Zn1—N1	78.20 (13)
C9—C10—H10	119.2	N2ⁱ—Zn1—N1ⁱ	78.20 (13)
C11—C10—H10	119.2	N2—Zn1—N1ⁱ	101.80 (13)
C12—C11—C10	116.1 (4)	N1—Zn1—N1ⁱ	180.000 (1)
C12—C11—C14	124.0 (4)	N2ⁱ—Zn1—O1ⁱ	89.48 (14)
C10—C11—C14	119.9 (5)	N2—Zn1—O1ⁱ	90.52 (14)
C13—C12—C11	123.1 (4)	N1—Zn1—O1ⁱ	88.42 (13)
C13—C12—H12	118.5	N1ⁱ—Zn1—O1ⁱ	91.58 (13)
C11—C12—H12	118.5	N2ⁱ—Zn1—O1	90.52 (14)
C12—C13—C8	120.2 (4)	N2—Zn1—O1	89.48 (14)
C12—C13—H13	119.9	N1—Zn1—O1	91.58 (13)
C8—C13—H13	119.9	N1ⁱ—Zn1—O1	88.42 (13)
C18—C14—C15	114.4 (5)	O1ⁱ—Zn1—O1	180.000 (1)
C18—C14—C11	124.8 (5)

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1W···N3ⁱⁱ	0.75 (6)	2.07 (6)	2.812 (5)	169 (6)
O1—H2W···N5ⁱⁱⁱ	0.85 (6)	2.38 (6)	3.165 (7)	155 (6)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₈H₁₂N₅)₂(H₂O)₂]
M_r	698.05
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.214 (5), 12.049 (5), 9.825 (4)
β (°)	100.709 (3)
V (Å³)	1537.0 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.85
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.905, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	7962, 2718, 1731
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.151, 1.00
No. of reflections	2718
No. of parameters	229
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.32

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1W···N3ⁱ	0.75 (6)	2.07 (6)	2.812 (5)	169 (6)
O1—H2W···N5ⁱⁱ	0.85 (6)	2.38 (6)	3.165 (7)	155 (6)

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

References

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