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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 67| Part 11| November 2011| Page m1598
doi:10.1107/S1600536811043455

Bis{μ-2-[1-(pyridin-2-yl­methyl­imino)­eth­yl]phenolato}bis­­(azido­zinc)

Jian-Ying Miaoa*

aDepartment of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721007, People's Republic of China
*Correspondence e-mail: jianying_miao@163.com

(Received 19 October 2011; accepted 19 October 2011; online 29 October 2011)

The title compound, [Zn2(C14H13N2O)2(N3)2], is a phenolate-bridged centrosymmetric dinuclear zinc(II) complex. The Zn⋯Zn distance is 3.076 (1) Å. Each Zn atom is five-coordinated by two O and two N atoms from two Schiff base ligands, and by one azide N atom, forming a square-pyramidal geometry.

Related literature

For background on zinc complexes with Schiff base ligands, see: Keypour et al. (2010[Keypour, H., Shayesteh, M., Nematollahi, D., Valencia, L. & Rudbari, H. A. (2010). J. Coord. Chem. 63, 4165-4176.]); Liu et al. (2011[Liu, H. Y., Li, G. W., Li, Z. L., Wu, J. Y. & Cai, Y. C. (2011). Russ. J. Coord. Chem. 37, 668-673.]); You et al. (2011[You, Z.-L., Lu, Y., Zhang, N., Ding, B.-W., Sun, H., Hou, P. & Wang, C. (2011). Polyhedron, 30, 2186-2194.]); Bhattacharjee et al. (2011[Bhattacharjee, C. R., Das, G., Mondal, P., Prasad, S. K. & Rao, D. S. S. (2011). Eur. J. Inorg. Chem. 9, 1418-1424.]); Das et al. (2010[Das, K., Mandal, T. N., Roy, S., Gupta, S., Barik, A. K., Mitra, P., Rheingold, A. L. & Kar, S. K. (2010). Polyhedron, 29, 2892-2899.]). For similar zinc complexes, see: Adams et al. (1995[Adams, H., Bailey, N. A., Bertrand, P., de Barbarin, C. O. R., Fenton, D. E. & Gou, S. (1995). J. Chem. Soc. Dalton Trans. pp. 275-279.]); You et al. (2009[You, Z.-L., Hou, P., Ni, L.-L. & Chen, S. (2009). Inorg. Chem. Commun. 12, 444-446.]); Zhou et al. (2008[Zhou, X.-R., Li, Z.-S., Zhang, L. & Zhou, Z.-H. (2008). Acta Cryst. E64, m791.]); Basak et al. (2007[Basak, S., Sen, S., Banerjee, S., Mitra, S., Rosair, G. & Rodriguez, M. T. G. (2007). Polyhedron, 26, 5104-5112.]).

[Scheme 1]

Experimental

Crystal data

  • [Zn2(C14H13N2O)2(N3)2]

  • Mr = 665.33

  • Monoclinic, P 21 /n

  • a = 10.057 (3) Å

  • b = 8.168 (3) Å

  • c = 16.741 (5) Å

  • β = 96.684 (3)°

  • V = 1365.8 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.80 mm−1

  • T = 298 K

  • 0.23 × 0.23 × 0.22 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.682, Tmax = 0.692

  • 10859 measured reflections

  • 2969 independent reflections

  • 2254 reflections with I > 2σ(I)

  • Rint = 0.039
Refinement

  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.074

  • S = 1.05

  • 2969 reflections

  • 191 parameters

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Selected bond lengths (Å)

Zn1—N3 1.986 (2)
Zn1—O1i 2.0321 (17)
Zn1—O1 2.0733 (17)
Zn1—N1 2.106 (2)
Zn1—N2 2.107 (2)
Symmetry code: (i) -x, -y+1, -z.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811043455/qm2038sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811043455/qm2038Isup2.hkl

checkCIF report


Comment top

Considerable attention has been focused on the zinc(II) complexes with multidentate Schiff base ligands (Keypour et al., 2010; Liu et al., 2011; You et al., 2011; Bhattacharjee et al., 2011; Das et al., 2010). As an extension of the work on the structural characterization of such complexes, the title new dinuclear zinc(II) complex is reported here.

The title compound is a phenolato-bridged dinuclear zinc(II) complex, as shown in Fig. 1. The Zn···Zn distance is 3.076 (1) Å. Each Zn atom is five-coordinated by two O and two N atoms from two Schiff base ligands, and by one azido N atom, forming a square pyramidal geometry. The bond lengths in the square pyramidal coordination are comparable with those reported in similar zinc complexes with Schiff bases (Adams et al., 1995; You et al., 2009; Zhou et al., 2008; Basak et al., 2007).

Related literature top

For background on zinc complexes with Schiff base ligands, see: Keypour et al. (2010); Liu et al. (2011); You et al. (2011); Bhattacharjee et al. (2011); Das et al. (2010). For similar zinc complexes, see: Adams et al. (1995); You et al. (2009); Zhou et al. (2008); Basak et al. (2007).

Experimental top

2-Acetylphenol (1 mmol, 136 mg), 2-aminomethylpyridine (1 mmol, 108 mg), sodium azide (1 mmol, 65 mg), and Zn(NO3)2.6H2O (1 mmol, 297 mg) were dissolved in MeOH (80 ml). The mixture was stirred at room temperature for 1 h to give a colorless solution. The resulting solution was kept in air for a week, and block colorless crystals were formed.

Refinement top

H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with Uiso(H) = 1.2 or 1.5Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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).

Figures top
[Figure 1] Fig. 1. The structure of the title complex, showing 30% displacement ellipsoids (arbitrary spheres for the H atoms).
Bis{µ-2-[1-(pyridin-2-ylmethylimino)ethyl]phenolato}bis(azidozinc) top
Crystal data top
[Zn2(C14H13N2O)2(N3)2]F(000) = 680
Mr = 665.33Dx = 1.618 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2133 reflections
a = 10.057 (3) Åθ = 2.3–24.5°
b = 8.168 (3) ŵ = 1.80 mm−1
c = 16.741 (5) ÅT = 298 K
β = 96.684 (3)°Block, colorless
V = 1365.8 (8) Å30.23 × 0.23 × 0.22 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer		2969 independent reflections
Radiation source: fine-focus sealed tube2254 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ω scansθmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→12
Tmin = 0.682, Tmax = 0.692k = −10→10
10859 measured reflectionsl = −20→21
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.029P)2 + 0.3081P]
where P = (Fo2 + 2Fc2)/3
2969 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.32 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
Crystal data top
[Zn2(C14H13N2O)2(N3)2]V = 1365.8 (8) Å3
Mr = 665.33Z = 2
Monoclinic, P21/nMo Kα radiation
a = 10.057 (3) ŵ = 1.80 mm−1
b = 8.168 (3) ÅT = 298 K
c = 16.741 (5) Å0.23 × 0.23 × 0.22 mm
β = 96.684 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2969 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2254 reflections with I > 2σ(I)
Tmin = 0.682, Tmax = 0.692Rint = 0.039
10859 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.074H-atom parameters constrained
S = 1.05Δρmax = 0.32 e Å−3
2969 reflectionsΔρmin = −0.29 e Å−3
191 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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn1−0.00948 (3)0.68795 (3)−0.001959 (16)0.03019 (10)
N10.0009 (2)0.7029 (2)0.12421 (12)0.0326 (5)
N2−0.1532 (2)0.8702 (2)0.01204 (12)0.0340 (5)
N30.0351 (2)0.7651 (3)−0.10817 (13)0.0431 (6)
N40.1167 (2)0.7042 (3)−0.14488 (13)0.0392 (5)
N50.1955 (3)0.6510 (3)−0.18282 (16)0.0595 (7)
O10.13472 (15)0.5071 (2)0.02040 (9)0.0301 (4)
C10.2225 (2)0.5932 (3)0.15413 (14)0.0334 (6)
C20.2369 (2)0.5228 (3)0.07861 (14)0.0298 (6)
C30.3638 (3)0.4688 (3)0.06437 (17)0.0406 (7)
H30.37370.41460.01660.049*
C40.4749 (3)0.4940 (4)0.11971 (18)0.0480 (7)
H40.55880.45960.10820.058*
C50.4617 (3)0.5702 (4)0.19199 (19)0.0525 (8)
H50.53690.59060.22850.063*
C60.3372 (3)0.6157 (3)0.20958 (16)0.0442 (7)
H60.32840.66250.25930.053*
C70.0908 (3)0.6441 (3)0.17739 (15)0.0342 (6)
C80.0687 (3)0.6214 (4)0.26424 (16)0.0560 (8)
H8A0.10820.71130.29550.084*
H8B0.10950.52080.28400.084*
H8C−0.02560.61770.26850.084*
C9−0.1276 (3)0.7576 (4)0.14743 (16)0.0431 (7)
H9A−0.11320.81360.19880.052*
H9B−0.18440.66340.15340.052*
C10−0.1962 (2)0.8714 (3)0.08491 (16)0.0355 (6)
C11−0.2991 (3)0.9726 (3)0.10270 (18)0.0459 (7)
H11−0.32870.97010.15330.055*
C12−0.3567 (3)1.0770 (4)0.0441 (2)0.0506 (8)
H12−0.42571.14650.05470.061*
C13−0.3116 (3)1.0777 (4)−0.03019 (19)0.0473 (7)
H13−0.34911.1481−0.07030.057*
C14−0.2102 (3)0.9730 (3)−0.04432 (17)0.0396 (7)
H14−0.18000.9733−0.09480.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.03556 (18)0.03175 (17)0.02340 (16)0.00139 (13)0.00400 (11)−0.00148 (14)
N10.0386 (12)0.0332 (12)0.0262 (11)0.0014 (9)0.0043 (9)−0.0025 (9)
N20.0413 (12)0.0299 (11)0.0308 (12)0.0010 (9)0.0041 (10)−0.0026 (9)
N30.0470 (14)0.0501 (15)0.0344 (13)0.0087 (11)0.0146 (11)0.0093 (11)
N40.0450 (13)0.0409 (14)0.0319 (13)−0.0022 (11)0.0045 (10)0.0062 (11)
N50.0658 (17)0.0638 (18)0.0530 (17)0.0110 (14)0.0245 (14)−0.0008 (14)
O10.0310 (9)0.0325 (9)0.0262 (8)−0.0003 (7)0.0005 (7)−0.0032 (8)
C10.0381 (14)0.0353 (15)0.0260 (14)−0.0031 (12)0.0006 (11)0.0024 (11)
C20.0314 (13)0.0274 (14)0.0301 (13)−0.0021 (10)0.0015 (10)0.0040 (10)
C30.0392 (15)0.0424 (17)0.0402 (16)0.0043 (12)0.0049 (12)−0.0018 (12)
C40.0339 (15)0.0534 (18)0.0560 (19)0.0030 (14)0.0016 (13)0.0051 (16)
C50.0433 (17)0.0581 (19)0.051 (2)−0.0048 (15)−0.0143 (15)0.0006 (16)
C60.0506 (17)0.0463 (17)0.0332 (15)−0.0013 (14)−0.0053 (13)−0.0014 (13)
C70.0453 (15)0.0340 (14)0.0238 (13)−0.0013 (12)0.0053 (11)−0.0027 (11)
C80.068 (2)0.072 (2)0.0289 (16)0.0102 (17)0.0078 (15)0.0062 (15)
C90.0452 (16)0.0507 (17)0.0359 (16)0.0090 (13)0.0150 (13)0.0021 (13)
C100.0360 (14)0.0336 (14)0.0376 (16)−0.0019 (11)0.0077 (12)−0.0054 (12)
C110.0395 (16)0.0498 (19)0.0503 (18)0.0043 (13)0.0136 (13)−0.0045 (14)
C120.0388 (16)0.0424 (17)0.071 (2)0.0083 (14)0.0086 (15)−0.0101 (16)
C130.0469 (17)0.0376 (16)0.056 (2)0.0049 (14)−0.0023 (15)0.0045 (15)
C140.0440 (16)0.0383 (17)0.0364 (15)−0.0016 (12)0.0036 (12)0.0003 (12)
Geometric parameters (Å, º) top
Zn1—N31.986 (2)C4—C51.381 (4)
Zn1—O1i2.0321 (17)C4—H40.9300
Zn1—O12.0733 (17)C5—C61.371 (4)
Zn1—N12.106 (2)C5—H50.9300
Zn1—N22.107 (2)C6—H60.9300
Zn1—Zn1i3.0763 (11)C7—C81.508 (3)
N1—C71.286 (3)C8—H8A0.9600
N1—C91.463 (3)C8—H8B0.9600
N2—C101.341 (3)C8—H8C0.9600
N2—C141.341 (3)C9—C101.506 (4)
N3—N41.190 (3)C9—H9A0.9700
N4—N51.157 (3)C9—H9B0.9700
O1—C21.338 (3)C10—C111.384 (3)
O1—Zn1i2.0321 (17)C11—C121.376 (4)
C1—C61.407 (3)C11—H110.9300
C1—C21.412 (3)C12—C131.372 (4)
C1—C71.482 (3)C12—H120.9300
C2—C31.396 (3)C13—C141.372 (4)
C3—C41.382 (4)C13—H130.9300
C3—H30.9300C14—H140.9300
N3—Zn1—O1i108.26 (9)C3—C4—H4119.9
N3—Zn1—O199.31 (8)C6—C5—C4119.6 (3)
O1i—Zn1—O182.94 (7)C6—C5—H5120.2
N3—Zn1—N1152.79 (9)C4—C5—H5120.2
O1i—Zn1—N198.94 (7)C5—C6—C1121.5 (3)
O1—Zn1—N184.73 (7)C5—C6—H6119.2
N3—Zn1—N296.00 (9)C1—C6—H6119.2
O1i—Zn1—N298.60 (8)N1—C7—C1120.0 (2)
O1—Zn1—N2163.29 (7)N1—C7—C8122.9 (2)
N1—Zn1—N278.59 (8)C1—C7—C8117.1 (2)
N3—Zn1—Zn1i108.42 (7)C7—C8—H8A109.5
O1i—Zn1—Zn1i41.98 (5)C7—C8—H8B109.5
O1—Zn1—Zn1i40.96 (5)H8A—C8—H8B109.5
N1—Zn1—Zn1i92.33 (6)C7—C8—H8C109.5
N2—Zn1—Zn1i138.10 (6)H8A—C8—H8C109.5
C7—N1—C9120.1 (2)H8B—C8—H8C109.5
C7—N1—Zn1128.44 (17)N1—C9—C10110.6 (2)
C9—N1—Zn1109.99 (15)N1—C9—H9A109.5
C10—N2—C14118.6 (2)C10—C9—H9A109.5
C10—N2—Zn1113.83 (17)N1—C9—H9B109.5
C14—N2—Zn1127.36 (18)C10—C9—H9B109.5
N4—N3—Zn1124.78 (19)H9A—C9—H9B108.1
N5—N4—N3176.9 (3)N2—C10—C11121.9 (3)
C2—O1—Zn1i126.58 (14)N2—C10—C9117.3 (2)
C2—O1—Zn1121.70 (14)C11—C10—C9120.8 (2)
Zn1i—O1—Zn197.06 (7)C12—C11—C10118.7 (3)
C6—C1—C2118.8 (2)C12—C11—H11120.7
C6—C1—C7118.7 (2)C10—C11—H11120.7
C2—C1—C7122.5 (2)C13—C12—C11119.5 (3)
O1—C2—C3119.0 (2)C13—C12—H12120.2
O1—C2—C1122.7 (2)C11—C12—H12120.2
C3—C2—C1118.2 (2)C14—C13—C12118.9 (3)
C4—C3—C2121.5 (3)C14—C13—H13120.5
C4—C3—H3119.3C12—C13—H13120.5
C2—C3—H3119.3N2—C14—C13122.3 (3)
C5—C4—C3120.1 (3)N2—C14—H14118.8
C5—C4—H4119.9C13—C14—H14118.8
Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula[Zn2(C14H13N2O)2(N3)2]
Mr665.33
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)10.057 (3), 8.168 (3), 16.741 (5)
β (°) 96.684 (3)
V (Å3)1365.8 (8)
Z2
Radiation typeMo Kα
µ (mm−1)1.80
Crystal size (mm)0.23 × 0.23 × 0.22
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.682, 0.692
No. of measured, independent and
observed [I > 2σ(I)] reflections		10859, 2969, 2254
Rint0.039
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.074, 1.05
No. of reflections2969
No. of parameters191
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.32, −0.29

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Zn1—N31.986 (2)Zn1—N12.106 (2)
Zn1—O1i2.0321 (17)Zn1—N22.107 (2)
Zn1—O12.0733 (17)
Symmetry code: (i) −x, −y+1, −z.
 

Acknowledgements

The author acknowledges the support of the Key Research Item of Baoji University of Arts and Sciences (grant No. ZK1034).

References

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ISSN: 2056-9890
Volume 67| Part 11| November 2011| Page m1598
doi:10.1107/S1600536811043455
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