metal-organic compounds
Diaquabis[5-(pyrazin-2-yl-κN1)-3-(pyridin-3-yl)-1,2,4-triazolido-κN1]zinc
aCollege of Materials & Chemical Engineering, China Three Gorges University, Yichang 443002, People's Republic of China
*Correspondence e-mail: dongww1@126.com
In the title compound, [Zn(C11H7N6)2(H2O)2], the ZnII cation, located on an inversion center, is N,N′-chelated by two 5-(pyrazin-2-yl)-3-(pyridin-3-yl)-1,2,4-triazolide anions and is further coordinated by two water molecules in a distorted N4O2 octahedral geometry. In the anionic ligand, the pyrazine and pyridine rings are twisted with respect to the central triazole ring by 5.77 (10) and 11.54 (10)°, respectively. In the crystal, classical O—H⋯N and weak C—H⋯O hydrogen bonds and π–π stacking interactions between aromatic rings [the centroid–centroid distances between triazole and pyrazine rings, and between triazole and pyridine rings are 3.623 (2) and 3.852 (2) Å, respectively] connect the molecules into a three-dimensional supramolecular architecture.
CCDC reference: 988429
Related literature
For applications and related structures of 1,2,4-triazole derivatives, see: Zhang et al. (2012); Chen et al. (2006).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; 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: SHELXTL.
Supporting information
CCDC reference: 988429
10.1107/S1600536814004176/xu5772sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814004176/xu5772Isup2.hkl
A mixture of 2-(5-(pyridin-3-yl)-4H-1,2,4-triazol-3-yl)pyrazine (0.0448 g, 0.2 mmol), Zn(CH3COO)2.2H2O (0.0220 g, 0.1 mmol), water (6 mL), N,N-dimethylformamide (2 mL) was stirred vigorously for 30 min and then sealed in a Teflon-lined stainless-steel autoclave. The autoclave was heated and maintained at 433 K for 3 d, and then cooled to room temperature at 5 K h-1 to obtain crystals suitable for X-ray analysis.
All H-atoms were positioned geometrically and refined using a riding model with C–H = 0.93 Å, Uiso(H) = 1.2 Ueq(C) for aromatic hydrogen atoms. The H-atoms of O atoms were identified from a difference Fourier map and refined with O–H = 0.85 (2) Å, Uiso(H) = 1.5Ueq(O).
Data collection: SMART (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).Fig. 1. The structure of the title compound showing the atomic numbering and 30% probability displacement ellipsoids. | |
Fig. 2. A packing diagram. |
[Zn(C11H7N6)2(H2O)2] | F(000) = 560 |
Mr = 547.85 | Dx = 1.686 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2880 reflections |
a = 8.600 (5) Å | θ = 2.4–27.6° |
b = 5.728 (3) Å | µ = 1.19 mm−1 |
c = 22.288 (12) Å | T = 296 K |
β = 100.646 (6)° | Prism, colorless |
V = 1079.0 (10) Å3 | 0.18 × 0.15 × 0.13 mm |
Z = 2 |
Bruker SMART 1000 CCD diffractometer | 2493 independent reflections |
Radiation source: fine-focus sealed tube | 2304 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.083 |
phi and ω scans | θmax = 27.6°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −11→11 |
Tmin = 0.80, Tmax = 0.86 | k = −7→7 |
11003 measured reflections | l = −29→28 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0623P)2 + 0.2938P] where P = (Fo2 + 2Fc2)/3 |
2493 reflections | (Δ/σ)max < 0.001 |
175 parameters | Δρmax = 0.44 e Å−3 |
3 restraints | Δρmin = −0.59 e Å−3 |
[Zn(C11H7N6)2(H2O)2] | V = 1079.0 (10) Å3 |
Mr = 547.85 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.600 (5) Å | µ = 1.19 mm−1 |
b = 5.728 (3) Å | T = 296 K |
c = 22.288 (12) Å | 0.18 × 0.15 × 0.13 mm |
β = 100.646 (6)° |
Bruker SMART 1000 CCD diffractometer | 2493 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2304 reflections with I > 2σ(I) |
Tmin = 0.80, Tmax = 0.86 | Rint = 0.083 |
11003 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 3 restraints |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.44 e Å−3 |
2493 reflections | Δρmin = −0.59 e Å−3 |
175 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.0000 | 1.0000 | 0.5000 | 0.02623 (14) | |
O1 | 0.17564 (15) | 0.7938 (2) | 0.47155 (6) | 0.0298 (3) | |
H1B | 0.218 (3) | 0.679 (4) | 0.4940 (11) | 0.045* | |
H1A | 0.252 (3) | 0.871 (4) | 0.4624 (11) | 0.045* | |
N1 | −0.03718 (18) | 1.1583 (3) | 0.40926 (7) | 0.0255 (3) | |
N2 | −0.0898 (2) | 1.2803 (3) | 0.28622 (8) | 0.0364 (4) | |
N3 | −0.32425 (18) | 0.7016 (3) | 0.35570 (7) | 0.0273 (3) | |
N4 | −0.27382 (18) | 0.5864 (3) | 0.45419 (7) | 0.0271 (3) | |
N5 | −0.17912 (18) | 0.7731 (3) | 0.44860 (7) | 0.0258 (3) | |
N6 | −0.6262 (2) | 0.0459 (3) | 0.41338 (9) | 0.0357 (4) | |
C1 | 0.0312 (2) | 1.3446 (3) | 0.38951 (9) | 0.0302 (4) | |
H1 | 0.0992 | 1.4355 | 0.4174 | 0.036* | |
C2 | 0.0033 (3) | 1.4058 (3) | 0.32853 (9) | 0.0339 (4) | |
H2 | 0.0512 | 1.5393 | 0.3167 | 0.041* | |
C3 | −0.1585 (3) | 1.0954 (4) | 0.30615 (9) | 0.0331 (4) | |
H3 | −0.2251 | 1.0039 | 0.2779 | 0.040* | |
C4 | −0.1352 (2) | 1.0330 (3) | 0.36728 (9) | 0.0238 (4) | |
C5 | −0.2139 (2) | 0.8348 (3) | 0.38977 (8) | 0.0242 (4) | |
C6 | −0.3581 (2) | 0.5502 (3) | 0.39810 (9) | 0.0249 (4) | |
C7 | −0.4734 (2) | 0.3611 (3) | 0.38268 (8) | 0.0261 (4) | |
C8 | −0.5332 (2) | 0.3074 (4) | 0.32153 (9) | 0.0312 (4) | |
H8 | −0.5029 | 0.3951 | 0.2905 | 0.037* | |
C9 | −0.6372 (2) | 0.1240 (4) | 0.30748 (10) | 0.0353 (4) | |
H9 | −0.6783 | 0.0865 | 0.2671 | 0.042* | |
C10 | −0.6790 (3) | −0.0028 (3) | 0.35465 (12) | 0.0362 (5) | |
H10 | −0.7475 | −0.1285 | 0.3450 | 0.043* | |
C11 | −0.5265 (2) | 0.2270 (4) | 0.42666 (9) | 0.0317 (4) | |
H11 | −0.4912 | 0.2645 | 0.4675 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0291 (2) | 0.0287 (2) | 0.0197 (2) | −0.00523 (11) | 0.00119 (13) | 0.00147 (10) |
O1 | 0.0282 (7) | 0.0286 (7) | 0.0331 (7) | −0.0035 (5) | 0.0064 (5) | 0.0056 (5) |
N1 | 0.0268 (7) | 0.0255 (7) | 0.0238 (7) | −0.0033 (6) | 0.0040 (6) | 0.0002 (5) |
N2 | 0.0442 (10) | 0.0369 (9) | 0.0274 (8) | −0.0051 (8) | 0.0044 (7) | 0.0068 (7) |
N3 | 0.0269 (7) | 0.0293 (8) | 0.0249 (7) | −0.0060 (6) | 0.0023 (6) | 0.0017 (6) |
N4 | 0.0266 (7) | 0.0279 (8) | 0.0264 (8) | −0.0056 (6) | 0.0042 (6) | 0.0020 (6) |
N5 | 0.0273 (7) | 0.0253 (7) | 0.0240 (7) | −0.0057 (6) | 0.0030 (6) | 0.0013 (6) |
N6 | 0.0303 (9) | 0.0395 (9) | 0.0382 (10) | −0.0096 (7) | 0.0089 (8) | 0.0040 (8) |
C1 | 0.0326 (9) | 0.0266 (9) | 0.0314 (9) | −0.0077 (7) | 0.0059 (7) | −0.0027 (7) |
C2 | 0.0414 (11) | 0.0271 (9) | 0.0344 (10) | −0.0045 (8) | 0.0105 (8) | 0.0050 (8) |
C3 | 0.0386 (10) | 0.0359 (10) | 0.0234 (9) | −0.0081 (8) | 0.0018 (7) | 0.0009 (8) |
C4 | 0.0229 (8) | 0.0257 (8) | 0.0227 (9) | −0.0007 (6) | 0.0036 (7) | 0.0005 (6) |
C5 | 0.0237 (8) | 0.0266 (9) | 0.0222 (8) | −0.0032 (7) | 0.0036 (6) | 0.0002 (6) |
C6 | 0.0212 (8) | 0.0289 (8) | 0.0246 (9) | −0.0035 (7) | 0.0041 (7) | 0.0005 (7) |
C7 | 0.0203 (8) | 0.0277 (8) | 0.0300 (9) | −0.0035 (7) | 0.0040 (7) | −0.0002 (7) |
C8 | 0.0295 (9) | 0.0353 (10) | 0.0281 (9) | −0.0078 (8) | 0.0040 (7) | 0.0013 (8) |
C9 | 0.0318 (10) | 0.0409 (11) | 0.0324 (10) | −0.0073 (8) | 0.0036 (8) | −0.0064 (8) |
C10 | 0.0306 (11) | 0.0336 (12) | 0.0442 (14) | −0.0114 (7) | 0.0063 (10) | −0.0056 (8) |
C11 | 0.0250 (8) | 0.0396 (10) | 0.0304 (9) | −0.0077 (8) | 0.0048 (7) | 0.0014 (8) |
Zn1—O1i | 2.1054 (16) | N6—C10 | 1.334 (3) |
Zn1—O1 | 2.1054 (16) | N6—C11 | 1.344 (3) |
Zn1—N1 | 2.1853 (18) | C1—C2 | 1.381 (3) |
Zn1—N1i | 2.1853 (18) | C1—H1 | 0.9300 |
Zn1—N5 | 2.1733 (16) | C2—H2 | 0.9300 |
Zn1—N5i | 2.1733 (16) | C3—C4 | 1.387 (3) |
O1—H1B | 0.867 (16) | C3—H3 | 0.9300 |
O1—H1A | 0.848 (16) | C4—C5 | 1.457 (2) |
N1—C1 | 1.332 (2) | C6—C7 | 1.466 (3) |
N1—C4 | 1.345 (2) | C7—C11 | 1.387 (3) |
N2—C3 | 1.329 (3) | C7—C8 | 1.399 (3) |
N2—C2 | 1.330 (3) | C8—C9 | 1.377 (3) |
N3—C5 | 1.339 (2) | C8—H8 | 0.9300 |
N3—C6 | 1.353 (2) | C9—C10 | 1.379 (3) |
N4—C6 | 1.340 (2) | C9—H9 | 0.9300 |
N4—N5 | 1.364 (2) | C10—H10 | 0.9300 |
N5—C5 | 1.338 (2) | C11—H11 | 0.9300 |
O1i—Zn1—O1 | 180.00 (7) | N2—C2—C1 | 122.23 (18) |
O1i—Zn1—N5 | 90.93 (7) | N2—C2—H2 | 118.9 |
O1—Zn1—N5 | 89.07 (7) | C1—C2—H2 | 118.9 |
O1i—Zn1—N5i | 89.07 (7) | N2—C3—C4 | 122.76 (18) |
O1—Zn1—N5i | 90.93 (7) | N2—C3—H3 | 118.6 |
N5—Zn1—N5i | 180.0 | C4—C3—H3 | 118.6 |
O1i—Zn1—N1 | 93.18 (6) | N1—C4—C3 | 120.28 (17) |
O1—Zn1—N1 | 86.82 (6) | N1—C4—C5 | 116.58 (17) |
N5—Zn1—N1 | 78.00 (6) | C3—C4—C5 | 123.13 (17) |
N5i—Zn1—N1 | 102.00 (6) | N5—C5—N3 | 114.31 (16) |
O1i—Zn1—N1i | 86.82 (6) | N5—C5—C4 | 120.63 (16) |
O1—Zn1—N1i | 93.18 (6) | N3—C5—C4 | 125.06 (16) |
N5—Zn1—N1i | 102.00 (6) | N4—C6—N3 | 113.79 (17) |
N5i—Zn1—N1i | 78.00 (6) | N4—C6—C7 | 123.96 (17) |
N1—Zn1—N1i | 180.000 (1) | N3—C6—C7 | 122.22 (17) |
Zn1—O1—H1B | 120.2 (18) | C11—C7—C8 | 117.17 (17) |
Zn1—O1—H1A | 114.1 (18) | C11—C7—C6 | 122.69 (17) |
H1B—O1—H1A | 106 (2) | C8—C7—C6 | 120.14 (17) |
C1—N1—C4 | 117.11 (16) | C9—C8—C7 | 119.71 (18) |
C1—N1—Zn1 | 129.81 (13) | C9—C8—H8 | 120.1 |
C4—N1—Zn1 | 112.83 (12) | C7—C8—H8 | 120.1 |
C3—N2—C2 | 116.14 (17) | C8—C9—C10 | 118.57 (19) |
C5—N3—C6 | 100.99 (15) | C8—C9—H9 | 120.7 |
C6—N4—N5 | 105.37 (15) | C10—C9—H9 | 120.7 |
C5—N5—N4 | 105.55 (14) | N6—C10—C9 | 123.25 (19) |
C5—N5—Zn1 | 111.52 (11) | N6—C10—H10 | 118.4 |
N4—N5—Zn1 | 142.93 (12) | C9—C10—H10 | 118.4 |
C10—N6—C11 | 117.76 (19) | N6—C11—C7 | 123.48 (19) |
N1—C1—C2 | 121.43 (18) | N6—C11—H11 | 118.3 |
N1—C1—H1 | 119.3 | C7—C11—H11 | 118.3 |
C2—C1—H1 | 119.3 |
Symmetry code: (i) −x, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N6ii | 0.85 (2) | 1.93 (2) | 2.736 (2) | 159 (2) |
O1—H1B···N4iii | 0.87 (2) | 1.91 (2) | 2.771 (2) | 170 (2) |
C1—H1···O1iv | 0.93 | 2.41 | 3.266 (3) | 153 |
Symmetry codes: (ii) x+1, y+1, z; (iii) −x, −y+1, −z+1; (iv) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N6i | 0.848 (16) | 1.928 (17) | 2.736 (2) | 159 (2) |
O1—H1B···N4ii | 0.867 (16) | 1.914 (16) | 2.771 (2) | 170 (2) |
C1—H1···O1iii | 0.93 | 2.41 | 3.266 (3) | 153 |
Symmetry codes: (i) x+1, y+1, z; (ii) −x, −y+1, −z+1; (iii) x, y+1, z. |
Acknowledgements
The authors are grateful to the Project of Hubei Provincial Education Office, China (grant No. Q20131304).
References
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1,2,4-Triazole derivatives are important building blocks of many important compounds widely used in medicine, agriculture, industry, and coordination chemistry (Zhang et al., 2012; Chen et al., 2006). During the synthesis of polymeric complexes using 2-(5-(pyridin-3-yl)-4H-1,2,4-triazol-3-yl)pyrazine as building blocks and, to our surprise, the title monomeric Zn(II) complex was obtained.
The title compound is a crstallographically centrosymmetric mononuclear complex. The ZnII cation is in a distaorted octahedral geometry (Fig. 1) and is coordinated by four N atoms from two 2-(5-(pyridin-3-yl)-1,2,4-triazolido-3-yl)pyrazine ligands and two coordinated water molecules. The observed Zn–O and Zn–N bond distances and bond angles reveal usual values. In the crystal, classic O–H···N hydrogen bonds, weak C—H···O hydrogen bond and π-π stacking between aromatic rings connect the molecules into the three dimensional supramolecular architecture [centroids between triazole and pyrazine rings and between triazole and pyridine rings being 3.623 (2) and 3.852 (2) Å, respectively].