metal-organic papers
Acta Cryst.(2005). E61, m1197–m1198 doi:10.1107/S1600536805015990 Han-Na Hou [Zn(C
13H16NO)2]
m1197
Acta Crystallographica Section E Structure Reports Online
ISSN 1600-5368
Bis[2-(cyclohexyliminomethyl)phenolato]zinc(II)
Han-Na Hou
Department of Chemistry, Hubei Institute of Education, Wuhan 430205, People’s Republic of China
Correspondence e-mail: houhanna@163.com
Key indicators
Single-crystal X-ray study
T= 298 K
Mean(C–C) = 0.004 A˚
Rfactor = 0.039
wRfactor = 0.105
Data-to-parameter ratio = 17.6
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography Printed in Great Britain – all rights reserved
The title compound, [Zn(C13H16NO)2], is a mononuclear
zinc(II) complex. The central ZnIIion, lying on an inversion centre, is coordinated by two N atoms and two O atoms from two Schiff base 2-cyclohexyliminomethylphenolate anions, resulting in a square-planar geometry.
Comment
Schiff base complexes have been studied extensively because
of their interesting structures and varied applications
(Bhaduri, et al., 2003; You, 2005). Zinc(II) has long been recognized as a structural template in protein folding or as a Lewis acid catalyst that can readily adopt 4-, 5- or 6-coordi-nation (Vallee & Auld, 1993; Lipscomb & Stra¨ter, 1996). As part of an investigation of the structures of Schiff base zinc(II) compounds, the title compound, (I) (Fig. 1), a mononuclear zinc(II) complex, is reported here.
The central ZnII ion, lying on an inversion centre, is in a square-planar geometry and is four-coordinated by two N atoms and two O atoms from two Schiff base molecules. Both
the Zn—O bond length of 1.891 (2) A˚ and the Zn—N bond
length of 2.015 (2) A˚ are comparable with the corresponding values observed in other Schiff base zinc(II) complexes (Kratochvı´l et al., 1991; Tatar et al., 1999). As expected, the cyclohexyl group adopts a chair conformation to minimize steric effects. There are no short intermolecular contacts in the crystal structure of (I) (Fig. 2).
Experimental
Salicylaldehyde (0.1 mmol, 12.1 mg), cyclohexylamine (0.1 mmol, 10.1 mg) and Zn(CH3COO)22H2O (0.1 mmol, 22.0 mg) were dissolved in methanol (10 ml). The mixture was stirred at room temperature for 1 h to give a clear yellow solution. After the solution had been kept in air for 3 d, yellow block-shaped crystals of (I) were formed.
Crystal data
[Zn(C13H16NO)2] Mr= 469.91 Triclinic,P1 a= 6.470 (2) A˚ b= 7.814 (2) A˚ c= 12.035 (2) A˚
= 97.70 (3) = 101.90 (3) = 104.88 (3)
V= 564.1 (3) A˚3
Z= 1
Dx= 1.383 Mg m3 MoKradiation Cell parameters from 3750
reflections
= 2.8–28.3 = 1.11 mm1 T= 298 (2) K Block, yellow 0.280.250.21 mm
Data collection
Bruker SMART CCD diffractometer
!scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin= 0.746,Tmax= 0.800 5204 measured reflections
2502 independent reflections 2457 reflections withI> 2(I) Rint= 0.056
max= 27.5 h=8!8 k=10!10 l=15!15
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.039 wR(F2) = 0.105 S= 1.14 2502 reflections 142 parameters
H-atom parameters constrained
w= 1/[2
(Fo2) + (0.0413P)2 + 0.3104P]
whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001
max= 0.42 e A˚
3 min=0.49 e A˚
[image:2.610.47.298.71.309.2]3
Table 1
Selected geometric parameters (A˚ ,).
Zn1—O1 1.891 (2) Zn1—N1 2.015 (2)
O1i
—Zn1—N1 89.54 (8) O1—Zn1—N1 90.46 (8)
Symmetry code: (i)x;yþ2;zþ2.
All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93–0.98 A˚ and with the constraintUiso(H) = 1.2Ueq(C) applied.
Data collection:SMART(Bruker, 1998); cell refinement:SAINT
(Bruker, 1998); 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.
The author thanks the Hubei Institute of Education for funding this study.
References
Bhaduri, S., Tasiopoulos, A. J., Bolcar, M. A., Abbound, K. A., Streib, W. E. & Christou, G. (2003).Inorg. Chem.42, 1483–1492.
Bruker (1998).SMART(Version 5.628) andSAINT(Version 6.02). Bruker AXS Inc., Madison, Wisconsin, USA.
Kratochvı´l, B., Ondra´cek, J., Novotny´, J. & Haber, V. (1991).Acta Cryst.C47, 2207–2209.
Lipscomb, W. N. & Stra¨ter, N. (1996).Chem. Rev.96, 2375–2434. Sheldrick, G. M. (1996).SADABS. University of Go¨ttingen, Germany. Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of
Go¨ttingen, Germany.
Sheldrick, G. M. (1997b).SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.
Tatar, L., U¨ lku¨, D. & Atakol, O. (1999).Acta Cryst.C55, 508–510. Vallee, B. L. & Auld, D. S. (1993).Acc. Chem. Res.26, 543–551. You, Z.-L. (2005).Acta Cryst.C61, m295–m297.
Figure 2
[image:2.610.316.568.72.235.2]The crystal packing in (I), viewed along theaaxis.
Figure 1
supporting information
sup-1 Acta Cryst. (2005). E61, m1197–m1198
supporting information
Acta Cryst. (2005). E61, m1197–m1198 [https://doi.org/10.1107/S1600536805015990]
Bis[2-(cyclohexyliminomethyl)phenolato]zinc(II)
Han-Na Hou
Bis(2-cyclohexyliminomethylphenolato)zinc(II)
Crystal data [Zn(C13H16NO)2] Mr = 469.91
Triclinic, P1 Hall symbol: -P 1 a = 6.470 (2) Å b = 7.814 (2) Å c = 12.035 (2) Å α = 97.70 (3)° β = 101.90 (3)° γ = 104.88 (3)° V = 564.1 (3) Å3
Z = 1 F(000) = 248 Dx = 1.383 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 3750 reflections θ = 2.8–28.3°
µ = 1.11 mm−1 T = 298 K Block, yellow
0.28 × 0.25 × 0.21 mm
Data collection Bruker SMART CCD
diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin = 0.746, Tmax = 0.800
5204 measured reflections 2502 independent reflections 2457 reflections with I > 2σ(I) Rint = 0.056
θmax = 27.5°, θmin = 1.8° h = −8→8
k = −10→10 l = −15→15
Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.039 wR(F2) = 0.105 S = 1.14 2502 reflections 142 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.0413P)2 + 0.3104P] where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001 Δρmax = 0.42 e Å−3 Δρmin = −0.49 e Å−3
Special details
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)
x y z Uiso*/Ueq
Zn1 0.0000 1.0000 1.0000 0.02973 (14)
O1 −0.1285 (3) 0.8932 (3) 0.84185 (14) 0.0409 (4) N1 0.2119 (3) 0.8502 (2) 1.00771 (15) 0.0270 (4) C1 0.1740 (4) 0.7962 (3) 0.79940 (19) 0.0294 (4) C2 −0.0230 (4) 0.8430 (3) 0.76706 (19) 0.0313 (5) C3 −0.1113 (5) 0.8304 (4) 0.6476 (2) 0.0417 (6)
H3 −0.2427 0.8582 0.6235 0.050*
C4 −0.0069 (5) 0.7777 (4) 0.5664 (2) 0.0479 (6)
H4 −0.0682 0.7715 0.4884 0.058*
C5 0.1894 (5) 0.7336 (4) 0.5991 (2) 0.0481 (6)
H5 0.2598 0.6990 0.5437 0.058*
C6 0.2765 (4) 0.7420 (3) 0.7138 (2) 0.0382 (5)
H6 0.4066 0.7114 0.7361 0.046*
C7 0.2698 (4) 0.7898 (3) 0.91772 (19) 0.0295 (4)
H7 0.3840 0.7371 0.9301 0.035*
C8 0.3129 (3) 0.8153 (3) 1.12203 (18) 0.0279 (4)
H8 0.3703 0.9320 1.1761 0.034*
C9 0.5023 (4) 0.7328 (3) 1.1279 (2) 0.0342 (5)
H9A 0.6183 0.8077 1.1006 0.041*
H9B 0.4506 0.6138 1.0784 0.041*
C10 0.5931 (4) 0.7182 (4) 1.2529 (2) 0.0407 (6)
H10A 0.7115 0.6626 1.2562 0.049*
H10B 0.6538 0.8383 1.3010 0.049*
C11 0.4134 (4) 0.6065 (4) 1.3001 (2) 0.0429 (6)
H11A 0.3654 0.4825 1.2579 0.051*
H11B 0.4735 0.6067 1.3810 0.051*
C12 0.2177 (4) 0.6798 (4) 1.2894 (2) 0.0396 (5)
H12A 0.2609 0.7971 1.3403 0.047*
H12B 0.1015 0.5996 1.3137 0.047*
C13 0.1301 (4) 0.6979 (3) 1.1653 (2) 0.0356 (5)
H13A 0.0100 0.7517 1.1618 0.043*
H13B 0.0727 0.5791 1.1156 0.043*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
supporting information
sup-3 Acta Cryst. (2005). E61, m1197–m1198
C2 0.0338 (11) 0.0293 (10) 0.0295 (10) 0.0103 (8) 0.0061 (9) 0.0023 (8) C3 0.0421 (14) 0.0485 (14) 0.0318 (12) 0.0184 (11) 0.0004 (10) 0.0031 (10) C4 0.0575 (17) 0.0590 (16) 0.0257 (11) 0.0186 (13) 0.0070 (11) 0.0059 (11) C5 0.0546 (17) 0.0617 (17) 0.0335 (13) 0.0215 (13) 0.0199 (12) 0.0059 (12) C6 0.0379 (13) 0.0463 (13) 0.0367 (12) 0.0187 (10) 0.0151 (10) 0.0077 (10) C7 0.0283 (10) 0.0310 (10) 0.0334 (11) 0.0138 (8) 0.0093 (8) 0.0085 (8) C8 0.0258 (10) 0.0325 (10) 0.0286 (10) 0.0119 (8) 0.0074 (8) 0.0091 (8) C9 0.0303 (11) 0.0411 (12) 0.0396 (12) 0.0168 (9) 0.0137 (9) 0.0159 (10) C10 0.0288 (11) 0.0543 (14) 0.0453 (14) 0.0177 (10) 0.0078 (10) 0.0230 (12) C11 0.0430 (14) 0.0496 (14) 0.0453 (14) 0.0196 (11) 0.0131 (11) 0.0254 (12) C12 0.0394 (13) 0.0493 (14) 0.0377 (12) 0.0161 (11) 0.0158 (10) 0.0194 (11) C13 0.0266 (10) 0.0469 (13) 0.0370 (12) 0.0114 (9) 0.0107 (9) 0.0153 (10)
Geometric parameters (Å, º)
Zn1—O1i 1.891 (2) C7—H7 0.9300
Zn1—O1 1.891 (2) C8—C9 1.518 (3)
Zn1—N1 2.015 (2) C8—C13 1.529 (3)
Zn1—N1i 2.015 (2) C8—H8 0.9800
O1—C2 1.314 (3) C9—C10 1.530 (3)
N1—C7 1.287 (3) C9—H9A 0.9700
N1—C8 1.488 (3) C9—H9B 0.9700
C1—C2 1.409 (3) C10—C11 1.523 (4)
C1—C6 1.410 (3) C10—H10A 0.9700
C1—C7 1.444 (3) C10—H10B 0.9700
C2—C3 1.413 (3) C11—C12 1.508 (4)
C3—C4 1.374 (4) C11—H11A 0.9700
C3—H3 0.9300 C11—H11B 0.9700
C4—C5 1.393 (4) C12—C13 1.523 (3)
C4—H4 0.9300 C12—H12A 0.9700
C5—C6 1.366 (4) C12—H12B 0.9700
C5—H5 0.9300 C13—H13A 0.9700
C6—H6 0.9300 C13—H13B 0.9700
O1i—Zn1—O1 180.0 N1—C8—H8 107.0
O1i—Zn1—N1 89.54 (8) C9—C8—H8 107.0
O1—Zn1—N1 90.46 (8) C13—C8—H8 107.0
O1i—Zn1—N1i 90.46 (8) C8—C9—C10 109.5 (2)
O1—Zn1—N1i 89.54 (8) C8—C9—H9A 109.8
N1—Zn1—N1i 180.0 C10—C9—H9A 109.8
C2—O1—Zn1 125.65 (15) C8—C9—H9B 109.8
C7—N1—C8 118.86 (19) C10—C9—H9B 109.8
C7—N1—Zn1 122.11 (15) H9A—C9—H9B 108.2
C8—N1—Zn1 118.97 (14) C11—C10—C9 111.3 (2)
C2—C1—C6 119.9 (2) C11—C10—H10A 109.4
C2—C1—C7 122.2 (2) C9—C10—H10A 109.4
C6—C1—C7 117.8 (2) C11—C10—H10B 109.4
O1—C2—C3 119.4 (2) H10A—C10—H10B 108.0
C1—C2—C3 117.3 (2) C12—C11—C10 111.6 (2)
C4—C3—C2 121.3 (2) C12—C11—H11A 109.3
C4—C3—H3 119.3 C10—C11—H11A 109.3
C2—C3—H3 119.3 C12—C11—H11B 109.3
C3—C4—C5 121.1 (2) C10—C11—H11B 109.3
C3—C4—H4 119.5 H11A—C11—H11B 108.0
C5—C4—H4 119.5 C11—C12—C13 111.2 (2)
C6—C5—C4 118.8 (2) C11—C12—H12A 109.4
C6—C5—H5 120.6 C13—C12—H12A 109.4
C4—C5—H5 120.6 C11—C12—H12B 109.4
C5—C6—C1 121.6 (2) C13—C12—H12B 109.4
C5—C6—H6 119.2 H12A—C12—H12B 108.0
C1—C6—H6 119.2 C12—C13—C8 110.77 (19)
N1—C7—C1 126.1 (2) C12—C13—H13A 109.5
N1—C7—H7 116.9 C8—C13—H13A 109.5
C1—C7—H7 116.9 C12—C13—H13B 109.5
N1—C8—C9 117.15 (18) C8—C13—H13B 109.5
N1—C8—C13 108.41 (17) H13A—C13—H13B 108.1 C9—C8—C13 109.88 (18)
N1—Zn1—O1—C2 −34.5 (2) C7—C1—C6—C5 176.0 (2) N1i—Zn1—O1—C2 145.5 (2) C8—N1—C7—C1 173.74 (19) O1i—Zn1—N1—C7 −154.02 (18) Zn1—N1—C7—C1 −9.2 (3) O1—Zn1—N1—C7 25.98 (18) C2—C1—C7—N1 −11.3 (3) O1i—Zn1—N1—C8 23.05 (15) C6—C1—C7—N1 172.8 (2) O1—Zn1—N1—C8 −156.95 (15) C7—N1—C8—C9 8.3 (3) Zn1—O1—C2—C1 25.5 (3) Zn1—N1—C8—C9 −168.85 (15) Zn1—O1—C2—C3 −156.07 (18) C7—N1—C8—C13 −116.7 (2) C6—C1—C2—O1 179.4 (2) Zn1—N1—C8—C13 66.1 (2) C7—C1—C2—O1 3.6 (3) N1—C8—C9—C10 176.51 (19) C6—C1—C2—C3 1.0 (3) C13—C8—C9—C10 −59.2 (3) C7—C1—C2—C3 −174.9 (2) C8—C9—C10—C11 57.6 (3) O1—C2—C3—C4 −179.7 (2) C9—C10—C11—C12 −55.1 (3) C1—C2—C3—C4 −1.2 (4) C10—C11—C12—C13 53.9 (3) C2—C3—C4—C5 0.5 (4) C11—C12—C13—C8 −55.9 (3) C3—C4—C5—C6 0.5 (4) N1—C8—C13—C12 −172.0 (2) C4—C5—C6—C1 −0.7 (4) C9—C8—C13—C12 58.8 (3) C2—C1—C6—C5 0.0 (4)
