Bis(2-butyl­imino­methyl-5-methoxy­phenolato-κ2N,O1)zinc(II)

Yang, J.; Li, J.; Zhang, X.; Wang, Q.

doi:10.1107/S1600536809031109

metal-organic compounds

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Volume 65| Part 9| September 2009| Page m1062

doi:10.1107/S1600536809031109

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Bis(2-butyliminomethyl-5-methoxyphenolato-κ²N,O¹)zinc(II)

Jun Yang,^a Jin Li,^a Xian Zhang ^a and Qiang Wang ^a ^*

^aEngineering Research Center for Clean Production of Textile Dyeing and Printing, Ministry of Education, Wuhan 430073, People's Republic of China
^*Correspondence e-mail: qiangqiang_wang@163.com

(Received 4 August 2009; accepted 5 August 2009; online 12 August 2009)

In the centrosymmetric title compound, [Zn(C₁₂H₁₆NO₂)₂], the Zn^II centre is coordinated by two O,N-bidentate Schiff base ligands, resulting in a slightly distorted trans-ZnN₂O₂ square-planar geometry for the metal ion. Two short intramolecular C—H⋯O contacts occur in the molecule.

Related literature

For related structures, see: Zhu et al. (2003 ); You et al. (2003 ).

Experimental

Crystal data

[Zn(C₁₂H₁₆NO₂)₂]
M_r = 477.89
Monoclinic, P 2₁ /c
a = 13.250 (4) Å
b = 4.8845 (15) Å
c = 17.858 (5) Å
β = 93.555 (5)°
V = 1153.6 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.10 mm⁻¹
T = 200 K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.734, T_max = 0.811
13300 measured reflections
2856 independent reflections
2438 reflections with I > 2σ(I)
R_int = 0.155

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.164
S = 1.10
2856 reflections
144 parameters
H-atom parameters constrained
Δρ_max = 1.13 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	1.8769 (17)
Zn1—N1ⁱ	2.004 (2)
Symmetry code: (i) -x+1, -y, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O1ⁱ	0.99	2.34	2.763 (3)	105
C9—H9A⋯O1ⁱ	0.99	2.55	3.087 (3)	114
Symmetry code: (i) -x+1, -y, -z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031109/hb5031sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031109/hb5031Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of the structures of zinc(II) complexes (Zhu et al., 2003; You et al., 2003), we now report the crystal structure of the title compound, (I).

Compound (I) consists of a Zn^II atom and two bidentate salicylal schiff base ligands (Fig. 1). The central Zn^II atom exhibits 4-coordination by two N atoms from imine moieties and two O-anions from salicylal groups, forming a slightly distorted square planar geometry (Table 1). Ring Zn1—N1—C7—C1—C2—O1 and Ring Zn1—N1A—C7A—C1A—C2A—O1A, togethor with the two benzene rings, stand in a plane with mean deviation of 0.0489 °. Two short intramolecular C—H···O contacts occur in the molecule (Table 2).

Related literature top

For related structures, see: Zhu et al. (2003); You et al. (2003).

Experimental top

0.5 mmol of zinc oxide, 1 mmol of 4-methoxysalicylaldehyde and 1 mmol of butylamine were dissolved in 10 ml methanol. After 3 ml ammonia was added, the result solution was then heated to 423 K for 10 h in a sealed vessel. The reactor was cooled to room temperature at a rate of 10 K h^-1. The mixture was filtered and held at room temperature for 8 d. Colourless blocks of (I) were isolated in 47% yield.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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

Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level and dashed lines indicate hydrogen bonds. Atoms with a label A suffix are generated by the symmetry operator (1–x, 1–y, –z).

Bis(2-butyliminomethyl-5-methoxyphenolato-κ²N,O¹)zinc(II) top

Crystal data top

[Zn(C₁₂H₁₆NO₂)₂]	F(000) = 504
M_r = 477.89	D_x = 1.376 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2317 reflections
a = 13.250 (4) Å	θ = 2.7–26.5°
b = 4.8845 (15) Å	µ = 1.10 mm⁻¹
c = 17.858 (5) Å	T = 200 K
β = 93.555 (5)°	Block, colorless
V = 1153.6 (6) Å³	0.30 × 0.30 × 0.20 mm
Z = 2

Data collection top

Bruker APEX CCD diffractometer	2856 independent reflections
Radiation source: fine-focus sealed tube	2438 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.155
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→17
T_min = 0.734, T_max = 0.811	k = −6→6
13300 measured reflections	l = −23→23

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0665P)² + 0.1817P] where P = (F_o² + 2F_c²)/3
2856 reflections	(Δ/σ)_max < 0.001
144 parameters	Δρ_max = 1.13 e Å⁻³
0 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

[Zn(C₁₂H₁₆NO₂)₂]	V = 1153.6 (6) Å³
M_r = 477.89	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.250 (4) Å	µ = 1.10 mm⁻¹
b = 4.8845 (15) Å	T = 200 K
c = 17.858 (5) Å	0.30 × 0.30 × 0.20 mm
β = 93.555 (5)°

Data collection top

Bruker APEX CCD diffractometer	2856 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2438 reflections with I > 2σ(I)
T_min = 0.734, T_max = 0.811	R_int = 0.155
13300 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.10	Δρ_max = 1.13 e Å⁻³
2856 reflections	Δρ_min = −0.67 e Å⁻³
144 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

	x	y	z	U_iso*/U_eq
C1	0.40796 (16)	0.2347 (5)	0.15609 (13)	0.0375 (5)
C2	0.3582 (2)	0.0191 (5)	0.11694 (18)	0.0403 (6)
C3	0.26490 (19)	−0.0732 (6)	0.14142 (16)	0.0437 (6)
H3	0.2290	−0.2136	0.1143	0.052*
C4	0.2254 (2)	0.0377 (5)	0.20399 (17)	0.0425 (6)
C5	0.27511 (19)	0.2446 (6)	0.24413 (15)	0.0488 (6)
H5	0.2475	0.3196	0.2875	0.059*
C6	0.36504 (18)	0.3396 (6)	0.22021 (13)	0.0470 (6)
H6	0.3995	0.4811	0.2479	0.056*
C7	0.49911 (17)	0.3519 (5)	0.13234 (13)	0.0392 (5)
H4	0.5281	0.4936	0.1631	0.047*
C8	0.63958 (19)	0.4507 (5)	0.06201 (16)	0.0386 (5)
H8A	0.6392	0.6192	0.0928	0.046*
H8B	0.6393	0.5060	0.0087	0.046*
C9	0.73453 (16)	0.2898 (5)	0.08264 (15)	0.0458 (6)
H9A	0.7308	0.1105	0.0568	0.055*
H9B	0.7391	0.2551	0.1374	0.055*
C10	0.8289 (2)	0.4405 (6)	0.0612 (2)	0.0523 (7)
H10A	0.8212	0.4914	0.0075	0.063*
H10B	0.8362	0.6114	0.0909	0.063*
C11	0.92355 (19)	0.2690 (8)	0.0748 (2)	0.0713 (10)
H11A	0.9303	0.2131	0.1276	0.107*
H11B	0.9828	0.3769	0.0628	0.107*
H11C	0.9188	0.1059	0.0428	0.107*
C12	0.0780 (2)	−0.2452 (6)	0.18909 (18)	0.0582 (8)
H12A	0.0683	−0.1895	0.1364	0.087*
H12B	0.0119	−0.2684	0.2101	0.087*
H12C	0.1151	−0.4187	0.1924	0.087*
N1	0.54697 (13)	0.2884 (4)	0.07401 (11)	0.0366 (4)
O1	0.39291 (14)	−0.0997 (5)	0.05842 (11)	0.0542 (5)
O2	0.13414 (17)	−0.0399 (4)	0.23031 (14)	0.0539 (6)
Zn1	0.5000	0.0000	0.0000	0.0382 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0311 (11)	0.0452 (13)	0.0370 (11)	0.0012 (10)	0.0067 (9)	0.0032 (9)
C2	0.0334 (14)	0.0431 (15)	0.0463 (16)	0.0002 (9)	0.0159 (11)	0.0018 (9)
C3	0.0340 (12)	0.0495 (13)	0.0491 (15)	−0.0069 (12)	0.0153 (10)	−0.0039 (12)
C4	0.0299 (13)	0.0518 (15)	0.0474 (16)	0.0030 (10)	0.0165 (11)	0.0061 (11)
C5	0.0444 (13)	0.0631 (17)	0.0407 (13)	0.0016 (12)	0.0176 (10)	−0.0046 (11)
C6	0.0440 (13)	0.0555 (16)	0.0424 (13)	−0.0034 (12)	0.0087 (10)	−0.0067 (11)
C7	0.0335 (11)	0.0431 (13)	0.0409 (12)	−0.0017 (10)	0.0023 (9)	−0.0012 (10)
C8	0.0331 (12)	0.0362 (11)	0.0472 (14)	−0.0047 (10)	0.0089 (10)	0.0018 (10)
C9	0.0311 (11)	0.0490 (14)	0.0578 (15)	−0.0058 (10)	0.0073 (10)	0.0079 (11)
C10	0.0332 (14)	0.0565 (15)	0.0681 (19)	−0.0094 (13)	0.0101 (12)	0.0000 (15)
C11	0.0345 (14)	0.086 (2)	0.094 (2)	−0.0009 (14)	0.0141 (15)	−0.0003 (19)
C12	0.0362 (13)	0.0653 (19)	0.075 (2)	−0.0047 (13)	0.0203 (13)	0.0043 (15)
N1	0.0275 (9)	0.0381 (10)	0.0446 (10)	−0.0016 (8)	0.0068 (7)	0.0031 (8)
O1	0.0458 (10)	0.0578 (12)	0.0625 (12)	−0.0190 (10)	0.0321 (9)	−0.0203 (10)
O2	0.0384 (11)	0.0685 (13)	0.0578 (13)	−0.0067 (9)	0.0265 (9)	−0.0022 (9)
Zn1	0.0311 (3)	0.0394 (3)	0.0457 (3)	−0.00210 (13)	0.0137 (2)	−0.00106 (14)

Geometric parameters (Å, º) top

C1—C2	1.405 (4)	C9—C10	1.521 (4)
C1—C6	1.406 (3)	C9—H9A	0.9900
C1—C7	1.425 (3)	C9—H9B	0.9900
C2—O1	1.304 (3)	C10—C11	1.515 (4)
C2—C3	1.411 (4)	C10—H10A	0.9900
C3—C4	1.374 (4)	C10—H10B	0.9900
C3—H3	0.9500	C11—H11A	0.9800
C4—O2	1.377 (3)	C11—H11B	0.9800
C4—C5	1.382 (4)	C11—H11C	0.9800
C5—C6	1.371 (3)	C12—O2	1.426 (4)
C5—H5	0.9500	C12—H12A	0.9800
C6—H6	0.9500	C12—H12B	0.9800
C7—N1	1.291 (3)	C12—H12C	0.9800
C7—H4	0.9500	N1—Zn1	2.004 (2)
C8—N1	1.488 (3)	Zn1—O1	1.8769 (17)
C8—C9	1.510 (3)	Zn1—N1ⁱ	2.004 (2)
C8—H8A	0.9900	Zn1—O1ⁱ	1.8769 (17)
C8—H8B	0.9900	Zn1—O1ⁱ	1.8769 (17)

C2—C1—C6	118.5 (2)	C10—C9—H9B	109.2
C2—C1—C7	122.2 (2)	H9A—C9—H9B	107.9
C6—C1—C7	119.3 (2)	C11—C10—C9	112.2 (3)
O1—C2—C1	123.7 (3)	C11—C10—H10A	109.2
O1—C2—C3	117.7 (2)	C9—C10—H10A	109.2
C1—C2—C3	118.6 (3)	C11—C10—H10B	109.2
C4—C3—C2	120.8 (3)	C9—C10—H10B	109.2
C4—C3—H3	119.6	H10A—C10—H10B	107.9
C2—C3—H3	119.6	C10—C11—H11A	109.5
C3—C4—O2	123.8 (3)	C10—C11—H11B	109.5
C3—C4—C5	121.1 (3)	H11A—C11—H11B	109.5
O2—C4—C5	115.1 (3)	C10—C11—H11C	109.5
C6—C5—C4	118.8 (2)	H11A—C11—H11C	109.5
C6—C5—H5	120.6	H11B—C11—H11C	109.5
C4—C5—H5	120.6	O2—C12—H12A	109.5
C5—C6—C1	122.2 (2)	O2—C12—H12B	109.5
C5—C6—H6	118.9	H12A—C12—H12B	109.5
C1—C6—H6	118.9	O2—C12—H12C	109.5
N1—C7—C1	127.7 (2)	H12A—C12—H12C	109.5
N1—C7—H4	116.1	H12B—C12—H12C	109.5
C1—C7—H4	116.1	C7—N1—C8	116.0 (2)
N1—C8—C9	111.7 (2)	C7—N1—Zn1	123.59 (15)
N1—C8—H8A	109.3	C8—N1—Zn1	120.33 (16)
C9—C8—H8A	109.3	C2—O1—Zn1	130.26 (18)
N1—C8—H8B	109.3	C4—O2—C12	117.3 (2)
C9—C8—H8B	109.3	O1ⁱ—Zn1—O1	180.0
H8A—C8—H8B	107.9	O1ⁱ—Zn1—N1ⁱ	91.74 (8)
C8—C9—C10	111.9 (2)	O1—Zn1—N1ⁱ	88.26 (8)
C8—C9—H9A	109.2	O1ⁱ—Zn1—N1	88.26 (8)
C10—C9—H9A	109.2	O1—Zn1—N1	91.74 (8)
C8—C9—H9B	109.2	N1ⁱ—Zn1—N1	180.0

C6—C1—C2—O1	−177.6 (3)	C9—C8—N1—C7	104.5 (3)
C7—C1—C2—O1	3.3 (4)	C9—C8—N1—Zn1	−77.6 (2)
C6—C1—C2—C3	3.2 (4)	C1—C2—O1—Zn1	−10.8 (4)
C7—C1—C2—C3	−175.9 (2)	C3—C2—O1—Zn1	168.5 (2)
O1—C2—C3—C4	178.1 (3)	C3—C4—O2—C12	−0.7 (4)
C1—C2—C3—C4	−2.6 (4)	C5—C4—O2—C12	177.6 (3)
C2—C3—C4—O2	179.0 (3)	C2—O1—Zn1—O1ⁱ	−103.5 (2)
C2—C3—C4—C5	0.8 (4)	C2—O1—Zn1—O1ⁱ	−103.5 (2)
C3—C4—C5—C6	0.3 (4)	C2—O1—Zn1—N1ⁱ	−169.8 (3)
O2—C4—C5—C6	−178.0 (2)	C2—O1—Zn1—N1	10.2 (3)
C4—C5—C6—C1	0.3 (4)	C7—N1—Zn1—O1ⁱ	175.0 (2)
C2—C1—C6—C5	−2.1 (4)	C8—N1—Zn1—O1ⁱ	−2.69 (17)
C7—C1—C6—C5	177.0 (2)	C7—N1—Zn1—O1ⁱ	175.0 (2)
C2—C1—C7—N1	1.5 (4)	C8—N1—Zn1—O1ⁱ	−2.69 (17)
C6—C1—C7—N1	−177.5 (2)	C7—N1—Zn1—O1	−5.0 (2)
N1—C8—C9—C10	172.7 (2)	C8—N1—Zn1—O1	177.31 (17)
C8—C9—C10—C11	−174.5 (3)	C7—N1—Zn1—N1ⁱ	104.5 (4)
C1—C7—N1—C8	178.5 (2)	C8—N1—Zn1—N1ⁱ	−73.1 (2)
C1—C7—N1—Zn1	0.8 (3)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O1ⁱ	0.99	2.34	2.763 (3)	105
C9—H9A···O1ⁱ	0.99	2.55	3.087 (3)	114

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₂H₁₆NO₂)₂]
M_r	477.89
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	13.250 (4), 4.8845 (15), 17.858 (5)
β (°)	93.555 (5)
V (Å³)	1153.6 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.10
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.734, 0.811
No. of measured, independent and observed [I > 2σ(I)] reflections	13300, 2856, 2438
R_int	0.155
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.164, 1.10
No. of reflections	2856
No. of parameters	144
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.13, −0.67

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O1

1.8769 (17)

Zn1—N1ⁱ

2.004 (2)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O1ⁱ	0.99	2.34	2.763 (3)	105
C9—H9A···O1ⁱ	0.99	2.55	3.087 (3)	114

Symmetry code: (i) −x+1, −y, −z.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
You, Z.-L., Lin, Y.-S., Liu, W.-S., Tan, M.-Y. & Zhu, H.-L. (2003). Acta Cryst. E59, m1025–m1027. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhu, H.-L., Meng, F.-J., Wang, Z.-D. & Yang, F. (2003). Z. Kristallogr. New Cryst. Struct. 218, 321–322. CAS Google Scholar

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doi:10.1107/S1600536809031109

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