Bis(2-butyl-imino-methyl-5-methoxy-phenolato-κN,O)zinc(II).

In the centrosymmetric title compound, [Zn(C(12)H(16)NO(2))(2)], the Zn(II) centre is coordinated by two O,N-bidentate Schiff base ligands, resulting in a slightly distorted trans-ZnN(2)O(2) square-planar geometry for the metal ion. Two short intra-molecular C-H⋯O contacts occur in the mol-ecule.

Related literature

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

Experimental

Crystal data

[Zn(C12H16NO2)2]

M = 477.89

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.164

S = 1.10

2856 reflections

144 parameters

H-atom parameters constrained

Δρmax = 1.13 e Å−3

Δρmin = −0.67 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn(C12H16NO2)2]	F(000) = 504
Mr = 477.89	Dx = 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

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

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(Fo2) + (0.0665P)2 + 0.1817P] where P = (Fo2 + 2Fc2)/3
2856 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 1.13 e Å−3
0 restraints	Δρmin = −0.67 e Å−3

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
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)

	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)

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)

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

Table 1

Selected bond lengths (Å)

Zn1—O1	1.8769 (17)
Zn1—N1i	2.004 (2)

Symmetry code: (i) .

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) .