supplementary materials


Acta Cryst. (2007). E63, m1731    [ doi:10.1107/S1600536807024452 ]

Bis[2-(2-naphthyliminomethyl)phenolato-[kappa]2N,O]zinc(II)

J.-F. Dong, L.-Z. Li, L.-L. Xu, T. Xu and D.-Q. Wang

Abstract top

In the title complex, [Zn(C17H12NO)2], the ZnII ion is coordinated by two N,O-bidentate ligand molecules in a distorted tetrahedral geometry. The crystal packing may be stabilized by weak C-H...Cg interactions [Cg is a ring centroid; H...Cg = 2.95 Å].

Comment top

As part of our ongoing studies of Schiff bases, we report here the synthesis and crystal structure of the title compound, (I), (Fig. 1), a new zinc(II) complex with a bidentate Schiff base ligand derived from the condensation of salicylaldehyde and 2-naphthylamine.

The coordination around zinc is a distorted tetrahedon involving two O and N atoms of the ligands (Table 1). These bond lengths and angle values are similar to the reported values for related structures (Hokelek et al., 2000, Tatar et al., 1999).

In the crystal of (I), the relatively short intermolecular distances H17···Cg(1)i of 2.945Å and H4···Cg(2)ii of 2.947Å (symmetry code: (i) 1/2 + x, 1/2 - y, -1/2 + z; (ii) x - 1, y, z; Cg(1) and Cg(2) are the centroids of the C25–34 and C29–34 rings, respectively) indicate the presence of weak C—H···π interactions (Fig. 2), which stabilize the crystal packing along with van der Waals forces.

Related literature top

For related literature, see: Hokelek et al. (2000); Lipscomb & Strater (1996); Tatar et al. (1999).

Experimental top

2-Naphthylamine (1 mmol, 143.19 mg) was dissolved in hot methanol (10 ml) and added in portions to a methanol solution (3 ml) of salicylaldehyde (1 mmol, 0.11 ml). The mixture was then stirred at 323 K for 2 h. Subsequently, an aqueous solution (2 ml) of zinc acetate dihydrate (1 mmol, 219.5 mg) was added dropwise and stirred for another 5 h. The solution was held at room temperature for ten days, whereupon yellow blocks of (I) were obtained.

Refinement top

All the H atoms were geometrically placed (C—H = 0.93 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids (arbitrary spheres for the H atoms).
[Figure 2] Fig. 2. The C—H···π interactions (dashed lines) in the crystal structure of (I).
Bis[2-(2-naphthyliminomethyl)phenolato-κ2N,O]zinc(II) top
Crystal data top
[Zn(C17H12NO)2]F(000) = 1152
Mr = 557.92Dx = 1.437 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2565 reflections
a = 5.7616 (11) Åθ = 2.6–19.3°
b = 26.912 (3) ŵ = 0.99 mm1
c = 16.635 (2) ÅT = 298 K
β = 90.791 (2)°Block, yellow
V = 2579.0 (6) Å30.27 × 0.18 × 0.11 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
4398 independent reflections
Radiation source: fine-focus sealed tube2620 reflections with I > 2σ(I)
graphiteRint = 0.109
ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 66
Tmin = 0.776, Tmax = 0.899k = 2832
12472 measured reflectionsl = 1919
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)] = 0.123Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.323H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.1741P)2 + 8.9475P]
where P = (Fo2 + 2Fc2)/3
4398 reflections(Δ/σ)max = 0.002
352 parametersΔρmax = 1.51 e Å3
0 restraintsΔρmin = 1.04 e Å3
Crystal data top
[Zn(C17H12NO)2]V = 2579.0 (6) Å3
Mr = 557.92Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.7616 (11) ŵ = 0.99 mm1
b = 26.912 (3) ÅT = 298 K
c = 16.635 (2) Å0.27 × 0.18 × 0.11 mm
β = 90.791 (2)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
4398 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2620 reflections with I > 2σ(I)
Tmin = 0.776, Tmax = 0.899Rint = 0.109
12472 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.123H-atom parameters constrained
wR(F2) = 0.323Δρmax = 1.51 e Å3
S = 1.01Δρmin = 1.04 e Å3
4398 reflectionsAbsolute structure: ?
352 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Zn10.3650 (2)0.23346 (4)0.67332 (7)0.0501 (5)
N10.5696 (14)0.2282 (3)0.5763 (5)0.0467 (19)
N20.5939 (14)0.2372 (3)0.7685 (4)0.0414 (18)
O10.1839 (13)0.1768 (3)0.6500 (5)0.0590 (19)
O20.1955 (14)0.2908 (3)0.7000 (4)0.063 (2)
C10.5715 (19)0.1862 (5)0.5369 (7)0.060 (3)
H10.68080.18370.49650.072*
C20.4265 (19)0.1437 (4)0.5480 (6)0.053 (3)
C30.241 (2)0.1414 (4)0.6000 (7)0.057 (3)
C40.113 (3)0.0972 (4)0.5990 (7)0.078 (4)
H40.01400.09470.63250.094*
C50.166 (3)0.0577 (5)0.5514 (9)0.093 (5)
H50.07760.02890.55350.112*
C60.351 (3)0.0606 (5)0.5001 (9)0.092 (5)
H60.38870.03380.46760.111*
C70.477 (2)0.1028 (5)0.4975 (8)0.077 (4)
H70.59960.10500.46190.092*
C80.6637 (17)0.3146 (4)0.5780 (6)0.049 (2)
H80.52560.32000.60490.058*
C90.7230 (17)0.2665 (4)0.5553 (6)0.048 (2)
C100.9323 (19)0.2581 (4)0.5148 (8)0.062 (3)
H100.97270.22630.49840.074*
C111.0722 (18)0.2967 (4)0.5005 (6)0.052 (3)
H111.21270.29060.47550.062*
C121.0190 (17)0.3456 (4)0.5209 (6)0.051 (3)
C130.8093 (17)0.3550 (3)0.5608 (5)0.042 (2)
C140.750 (2)0.4042 (4)0.5842 (7)0.066 (3)
H140.61160.41020.61080.079*
C150.895 (2)0.4423 (4)0.5673 (7)0.065 (3)
H150.85560.47460.58170.078*
C161.103 (2)0.4333 (5)0.5287 (7)0.069 (3)
H161.20500.45950.51930.083*
C171.160 (2)0.3868 (5)0.5046 (8)0.067 (3)
H171.29590.38200.47640.080*
C180.6095 (19)0.2797 (4)0.8069 (6)0.054 (3)
H180.72860.28200.84500.065*
C190.4681 (19)0.3230 (4)0.7979 (6)0.054 (3)
C200.2714 (19)0.3266 (4)0.7466 (6)0.052 (3)
C210.148 (2)0.3713 (4)0.7471 (7)0.067 (3)
H210.01540.37460.71520.080*
C220.221 (3)0.4108 (5)0.7944 (9)0.087 (4)
H220.13430.43990.79430.104*
C230.415 (3)0.4082 (4)0.8406 (8)0.078 (4)
H230.46310.43590.86990.094*
C240.542 (2)0.3650 (5)0.8446 (8)0.076 (4)
H240.67390.36310.87730.091*
C250.6688 (18)0.1505 (4)0.7680 (6)0.051 (2)
H250.52660.14670.74160.061*
C260.7456 (16)0.1970 (4)0.7892 (6)0.047 (2)
C270.9610 (18)0.2040 (4)0.8274 (6)0.054 (3)
H271.01260.23590.83980.065*
C281.0951 (19)0.1636 (5)0.8463 (6)0.058 (3)
H281.23700.16790.87270.069*
C291.018 (2)0.1153 (5)0.8255 (6)0.062 (3)
C300.8047 (19)0.1086 (4)0.7862 (7)0.056 (3)
C310.734 (2)0.0605 (5)0.7634 (8)0.072 (3)
H310.59220.05630.73680.086*
C320.869 (3)0.0196 (5)0.7795 (9)0.084 (4)
H320.82060.01180.76340.100*
C331.084 (3)0.0262 (6)0.8213 (10)0.098 (5)
H331.17750.00110.83370.118*
C341.151 (2)0.0726 (6)0.8427 (9)0.083 (4)
H341.29200.07660.87000.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0603 (8)0.0492 (7)0.0408 (6)0.0029 (6)0.0011 (5)0.0036 (5)
N10.047 (5)0.042 (5)0.051 (5)0.002 (4)0.004 (4)0.001 (4)
N20.055 (5)0.037 (4)0.032 (4)0.001 (4)0.003 (3)0.004 (3)
O10.066 (5)0.043 (4)0.068 (5)0.007 (4)0.009 (4)0.012 (4)
O20.079 (5)0.055 (5)0.054 (4)0.008 (4)0.009 (4)0.009 (4)
C10.046 (6)0.072 (8)0.064 (7)0.002 (6)0.005 (5)0.002 (6)
C20.057 (7)0.050 (6)0.053 (6)0.006 (5)0.004 (5)0.002 (5)
C30.058 (7)0.046 (6)0.066 (7)0.007 (5)0.011 (5)0.011 (5)
C40.121 (12)0.055 (7)0.060 (7)0.033 (7)0.009 (7)0.003 (6)
C50.167 (16)0.040 (7)0.073 (9)0.028 (8)0.003 (10)0.009 (6)
C60.148 (15)0.043 (7)0.086 (10)0.014 (8)0.024 (10)0.020 (7)
C70.079 (9)0.073 (9)0.078 (8)0.007 (7)0.000 (7)0.014 (7)
C80.046 (6)0.057 (6)0.044 (5)0.014 (5)0.007 (4)0.007 (5)
C90.037 (5)0.057 (6)0.049 (5)0.009 (5)0.002 (4)0.003 (5)
C100.046 (6)0.061 (7)0.079 (8)0.003 (5)0.018 (5)0.014 (6)
C110.045 (6)0.073 (8)0.038 (5)0.009 (6)0.003 (4)0.003 (5)
C120.039 (6)0.063 (7)0.050 (6)0.006 (5)0.000 (4)0.017 (5)
C130.054 (6)0.037 (5)0.034 (5)0.000 (4)0.006 (4)0.001 (4)
C140.060 (7)0.069 (8)0.070 (8)0.006 (6)0.002 (6)0.013 (6)
C150.084 (9)0.039 (6)0.073 (8)0.001 (6)0.008 (7)0.004 (5)
C160.080 (9)0.061 (8)0.066 (7)0.015 (7)0.007 (6)0.020 (6)
C170.053 (7)0.070 (8)0.079 (8)0.014 (6)0.003 (6)0.017 (6)
C180.057 (7)0.059 (7)0.047 (6)0.011 (5)0.012 (5)0.004 (5)
C190.060 (7)0.058 (6)0.045 (6)0.002 (5)0.001 (5)0.009 (5)
C200.061 (7)0.048 (6)0.046 (6)0.000 (5)0.013 (5)0.003 (5)
C210.074 (8)0.064 (8)0.062 (7)0.017 (6)0.001 (6)0.002 (6)
C220.124 (13)0.050 (8)0.086 (10)0.015 (8)0.008 (9)0.006 (7)
C230.113 (12)0.037 (6)0.084 (9)0.001 (7)0.008 (8)0.015 (6)
C240.084 (9)0.061 (8)0.082 (9)0.003 (7)0.008 (7)0.027 (6)
C250.046 (6)0.049 (6)0.057 (6)0.001 (5)0.006 (5)0.010 (5)
C260.039 (6)0.060 (7)0.043 (5)0.003 (5)0.006 (4)0.007 (5)
C270.043 (6)0.062 (7)0.058 (6)0.002 (5)0.014 (5)0.006 (5)
C280.049 (7)0.085 (9)0.039 (5)0.000 (6)0.002 (4)0.001 (5)
C290.066 (8)0.073 (8)0.046 (6)0.017 (6)0.009 (5)0.018 (5)
C300.042 (6)0.058 (7)0.070 (7)0.001 (5)0.011 (5)0.002 (5)
C310.078 (9)0.066 (8)0.071 (8)0.005 (7)0.017 (6)0.006 (6)
C320.094 (11)0.046 (7)0.112 (11)0.009 (7)0.022 (9)0.021 (7)
C330.101 (12)0.087 (11)0.108 (12)0.033 (9)0.015 (10)0.042 (9)
C340.066 (9)0.091 (11)0.091 (10)0.018 (8)0.002 (7)0.028 (8)
Geometric parameters (Å, °) top
Zn1—O21.884 (8)C15—C161.390 (17)
Zn1—O11.885 (7)C15—H150.9300
Zn1—N12.016 (8)C16—C171.355 (17)
Zn1—N22.049 (8)C16—H160.9300
N1—C11.307 (14)C17—H170.9300
N1—C91.404 (12)C18—C191.428 (15)
N2—C181.314 (13)C18—H180.9300
N2—C261.429 (12)C19—C201.413 (15)
O1—C31.309 (13)C19—C241.433 (15)
O2—C201.308 (13)C20—C211.396 (14)
C1—C21.431 (15)C21—C221.382 (18)
C1—H10.9300C21—H210.9300
C2—C31.385 (15)C22—C231.347 (19)
C2—C71.418 (16)C22—H220.9300
C3—C41.398 (15)C23—C241.374 (17)
C4—C51.364 (18)C23—H230.9300
C4—H40.9300C24—H240.9300
C5—C61.38 (2)C25—C261.373 (14)
C5—H50.9300C25—C301.403 (14)
C6—C71.347 (19)C25—H250.9300
C6—H60.9300C26—C271.399 (14)
C7—H70.9300C27—C281.367 (15)
C8—C91.392 (13)C27—H270.9300
C8—C131.406 (13)C28—C291.417 (17)
C8—H80.9300C28—H280.9300
C9—C101.408 (14)C29—C301.393 (16)
C10—C111.338 (15)C29—C341.409 (17)
C10—H100.9300C30—C311.408 (16)
C11—C121.393 (14)C31—C321.370 (17)
C11—H110.9300C31—H310.9300
C12—C131.410 (14)C32—C331.43 (2)
C12—C171.402 (15)C32—H320.9300
C13—C141.424 (14)C33—C341.35 (2)
C14—C151.355 (16)C33—H330.9300
C14—H140.9300C34—H340.9300
O2—Zn1—O1115.1 (3)C16—C15—H15119.8
O2—Zn1—N1123.8 (3)C17—C16—C15120.5 (11)
O1—Zn1—N196.1 (3)C17—C16—H16119.7
O2—Zn1—N296.2 (3)C15—C16—H16119.7
O1—Zn1—N2123.2 (3)C16—C17—C12122.3 (12)
N1—Zn1—N2104.2 (3)C16—C17—H17118.9
C1—N1—C9119.9 (9)C12—C17—H17118.9
C1—N1—Zn1118.1 (7)N2—C18—C19128.7 (9)
C9—N1—Zn1121.7 (6)N2—C18—H18115.7
C18—N2—C26120.3 (9)C19—C18—H18115.7
C18—N2—Zn1117.2 (7)C20—C19—C18124.8 (9)
C26—N2—Zn1122.3 (6)C20—C19—C24120.2 (11)
C3—O1—Zn1125.2 (7)C18—C19—C24115.0 (10)
C20—O2—Zn1125.0 (7)O2—C20—C21118.2 (10)
N1—C1—C2128.2 (10)O2—C20—C19124.5 (10)
N1—C1—H1115.9C21—C20—C19117.3 (10)
C2—C1—H1115.9C22—C21—C20120.9 (12)
C3—C2—C1125.0 (10)C22—C21—H21119.5
C3—C2—C7120.1 (11)C20—C21—H21119.5
C1—C2—C7114.8 (11)C23—C22—C21121.9 (13)
O1—C3—C2124.5 (10)C23—C22—H22119.1
O1—C3—C4119.3 (11)C21—C22—H22119.1
C2—C3—C4116.2 (11)C22—C23—C24120.4 (12)
C5—C4—C3123.2 (13)C22—C23—H23119.8
C5—C4—H4118.4C24—C23—H23119.8
C3—C4—H4118.4C23—C24—C19119.1 (12)
C6—C5—C4119.8 (13)C23—C24—H24120.4
C6—C5—H5120.1C19—C24—H24120.4
C4—C5—H5120.1C26—C25—C30120.0 (10)
C7—C6—C5119.4 (12)C26—C25—H25120.0
C7—C6—H6120.3C30—C25—H25120.0
C5—C6—H6120.3C25—C26—C27121.3 (10)
C6—C7—C2121.3 (13)C25—C26—N2115.7 (9)
C6—C7—H7119.4C27—C26—N2122.9 (9)
C2—C7—H7119.4C28—C27—C26119.5 (10)
C9—C8—C13121.0 (9)C28—C27—H27120.3
C9—C8—H8119.5C26—C27—H27120.3
C13—C8—H8119.5C27—C28—C29119.9 (11)
C8—C9—N1117.2 (9)C27—C28—H28120.0
C8—C9—C10119.6 (9)C29—C28—H28120.0
N1—C9—C10123.2 (9)C30—C29—C28120.3 (10)
C11—C10—C9118.9 (10)C30—C29—C34117.7 (12)
C11—C10—H10120.5C28—C29—C34121.9 (12)
C9—C10—H10120.5C25—C30—C29118.8 (10)
C10—C11—C12123.6 (10)C25—C30—C31121.5 (11)
C10—C11—H11118.2C29—C30—C31119.7 (11)
C12—C11—H11118.2C32—C31—C30121.6 (14)
C11—C12—C13118.5 (9)C32—C31—H31119.2
C11—C12—C17124.8 (10)C30—C31—H31119.2
C13—C12—C17116.7 (10)C31—C32—C33119.0 (14)
C8—C13—C12118.3 (9)C31—C32—H32120.5
C8—C13—C14121.1 (9)C33—C32—H32120.5
C12—C13—C14120.6 (10)C34—C33—C32119.0 (13)
C15—C14—C13119.6 (11)C34—C33—H33120.5
C15—C14—H14120.2C32—C33—H33120.5
C13—C14—H14120.2C33—C34—C29123.1 (14)
C14—C15—C16120.3 (11)C33—C34—H34118.5
C14—C15—H15119.8C29—C34—H34118.5
Table 1
Selected geometric parameters (Å)
top
Zn1—O21.884 (8)Zn1—N12.016 (8)
Zn1—O11.885 (7)Zn1—N22.049 (8)
Acknowledgements top

The authors thank the Natural Science Foundation of Shandong Province (grant No. Y2004B02) for a research grant.

references
References top

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