Bis{(E)-2-meth-oxy-6-[(4-methyl-phen-yl)-imino-meth-yl]phenolato}zinc(II).

The title compound, [Zn(C(15)H(14)NO(2))(2)], contains a four-coordinate Zn atom located on a twofold rotation axis that exhibits a distorted tetra-hedral geometry by two phenolate O atoms and two azomethine N atoms of the Schiff base 2-methoxy-6-[(4-methyl-phen-yl)imino-meth-yl]phenolate ligands.

Related literature

For related literature, see: Bhattacharyya et al. (2002 ▶); Iyere et al. (2004 ▶); Müller et al. (2001 ▶); Yu et al. (2007 ▶); Zhou & Zhao (2007 ▶).

Experimental

Crystal data

[Zn(C15H14NO2)2]

M = 545.93

Monoclinic,

a = 14.0698 (4) Å

b = 16.3828 (5) Å

c = 12.0532 (3) Å

β = 107.5880 (10)°

V = 2648.42 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.97 mm−1

T = 296 (2) K

0.52 × 0.08 × 0.08 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.914, T max = 0.930

10967 measured reflections

3013 independent reflections

2523 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.096

S = 1.03

3013 reflections

168 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033102/at2636sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033102/at2636Isup2.hkl

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

[Zn(C15H14NO2)2]	F(000) = 1136
Mr = 545.93	Dx = 1.369 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4200 reflections
a = 14.0698 (4) Å	θ = 2.0–27.5°
b = 16.3828 (5) Å	µ = 0.97 mm−1
c = 12.0532 (3) Å	T = 296 K
β = 107.588 (1)°	Prism, orange
V = 2648.42 (13) Å3	0.52 × 0.08 × 0.08 mm
Z = 4

Bruker APEXII diffractometer	3013 independent reflections
Radiation source: fine-focus sealed tube	2523 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.914, Tmax = 0.930	k = −16→21
10967 measured reflections	l = −15→15

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0548P)2 + 1.3911P] where P = (Fo2 + 2Fc2)/3
3013 reflections	(Δ/σ)max < 0.001
168 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.27 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
Zn1	0.0000	0.029267 (18)	0.2500	0.03242 (12)
N1	0.04480 (11)	0.08214 (9)	0.12438 (13)	0.0314 (3)
O1	0.26186 (12)	−0.13463 (10)	0.42256 (14)	0.0539 (4)
O2	0.11926 (10)	−0.03384 (8)	0.31639 (12)	0.0386 (3)
C1	−0.1868 (3)	0.3361 (2)	−0.1614 (3)	0.0881 (10)
H1A	−0.1785	0.3347	−0.2376	0.132*
H1B	−0.1641	0.3876	−0.1253	0.132*
H1C	−0.2561	0.3291	−0.1680	0.132*
C2	−0.12681 (17)	0.26797 (15)	−0.0881 (2)	0.0526 (6)
C3	−0.07130 (16)	0.21486 (15)	−0.13218 (19)	0.0479 (5)
H3A	−0.0719	0.2207	−0.2091	0.058*
C4	−0.01499 (15)	0.15341 (13)	−0.06598 (17)	0.0393 (5)
H4A	0.0220	0.1188	−0.0982	0.047*
C5	−0.01341 (13)	0.14317 (11)	0.04915 (16)	0.0326 (4)
C6	−0.07168 (16)	0.19465 (15)	0.09294 (19)	0.0481 (5)
H6A	−0.0740	0.1874	0.1686	0.058*
C7	−0.12619 (19)	0.25644 (17)	0.0254 (2)	0.0587 (6)
H7A	−0.1634	0.2912	0.0571	0.070*
C8	0.12692 (13)	0.05742 (13)	0.10587 (17)	0.0344 (4)
H8A	0.1411	0.0807	0.0423	0.041*
C9	0.19768 (14)	−0.00060 (13)	0.17051 (17)	0.0340 (4)
C10	0.28175 (17)	−0.01304 (15)	0.1298 (2)	0.0492 (6)
H10A	0.2847	0.0137	0.0629	0.059*
C11	0.35710 (17)	−0.06289 (18)	0.1865 (2)	0.0611 (7)
H11A	0.4118	−0.0695	0.1593	0.073*
C12	0.35297 (16)	−0.10458 (16)	0.2861 (2)	0.0541 (6)
H12A	0.4050	−0.1390	0.3248	0.065*
C13	0.27268 (15)	−0.09502 (13)	0.32723 (18)	0.0411 (5)
C14	0.19242 (13)	−0.04184 (11)	0.27139 (17)	0.0321 (4)
C15	0.3448 (2)	−0.1804 (2)	0.4906 (3)	0.0850 (10)
H15A	0.3283	−0.2056	0.5543	0.128*
H15B	0.4009	−0.1448	0.5202	0.128*
H15C	0.3612	−0.2219	0.4431	0.128*

	U11	U22	U33	U12	U13	U23
Zn1	0.02977 (17)	0.0356 (2)	0.0350 (2)	0.000	0.01448 (13)	0.000
N1	0.0318 (7)	0.0305 (8)	0.0330 (8)	−0.0016 (6)	0.0113 (6)	−0.0010 (6)
O1	0.0533 (9)	0.0591 (10)	0.0499 (10)	0.0229 (8)	0.0166 (8)	0.0156 (8)
O2	0.0340 (7)	0.0464 (9)	0.0391 (8)	0.0076 (6)	0.0167 (6)	0.0083 (6)
C1	0.094 (2)	0.087 (2)	0.086 (2)	0.0422 (19)	0.0316 (19)	0.0423 (19)
C2	0.0495 (12)	0.0524 (14)	0.0538 (14)	0.0119 (11)	0.0124 (11)	0.0160 (11)
C3	0.0497 (12)	0.0564 (14)	0.0368 (12)	0.0018 (10)	0.0118 (10)	0.0095 (10)
C4	0.0425 (10)	0.0401 (12)	0.0357 (11)	0.0003 (9)	0.0123 (9)	−0.0037 (9)
C5	0.0322 (9)	0.0305 (10)	0.0356 (10)	−0.0026 (7)	0.0110 (8)	0.0003 (8)
C6	0.0486 (12)	0.0614 (15)	0.0368 (12)	0.0157 (11)	0.0166 (10)	0.0043 (10)
C7	0.0610 (14)	0.0629 (16)	0.0547 (14)	0.0272 (13)	0.0213 (12)	0.0037 (12)
C8	0.0344 (9)	0.0373 (10)	0.0344 (10)	−0.0048 (8)	0.0148 (8)	0.0001 (8)
C9	0.0308 (9)	0.0358 (10)	0.0378 (11)	−0.0009 (8)	0.0143 (8)	−0.0030 (9)
C10	0.0444 (12)	0.0583 (15)	0.0539 (14)	0.0054 (10)	0.0283 (11)	0.0048 (11)
C11	0.0429 (12)	0.0791 (18)	0.0708 (17)	0.0175 (13)	0.0312 (12)	0.0049 (15)
C12	0.0404 (11)	0.0606 (15)	0.0620 (15)	0.0184 (11)	0.0167 (11)	0.0040 (12)
C13	0.0399 (10)	0.0424 (12)	0.0400 (11)	0.0060 (9)	0.0106 (9)	−0.0013 (9)
C14	0.0291 (9)	0.0324 (10)	0.0349 (10)	−0.0012 (7)	0.0096 (8)	−0.0057 (8)
C15	0.078 (2)	0.098 (2)	0.077 (2)	0.0455 (18)	0.0210 (16)	0.0416 (19)

Zn1—O2i	1.9270 (13)	C5—C6	1.387 (3)
Zn1—O2	1.9270 (13)	C6—C7	1.378 (3)
Zn1—N1	2.0043 (15)	C6—H6A	0.9300
Zn1—N1i	2.0043 (15)	C7—H7A	0.9300
N1—C8	1.306 (2)	C8—C9	1.426 (3)
N1—C5	1.430 (2)	C8—H8A	0.9300
O1—C13	1.368 (2)	C9—C14	1.412 (3)
O1—C15	1.421 (3)	C9—C10	1.426 (2)
O2—C14	1.307 (2)	C10—C11	1.349 (3)
C1—C2	1.512 (3)	C10—H10A	0.9300
C1—H1A	0.9600	C11—C12	1.398 (3)
C1—H1B	0.9600	C11—H11A	0.9300
C1—H1C	0.9600	C12—C13	1.373 (3)
C2—C3	1.378 (3)	C12—H12A	0.9300
C2—C7	1.379 (3)	C13—C14	1.424 (3)
C3—C4	1.377 (3)	C15—H15A	0.9600
C3—H3A	0.9300	C15—H15B	0.9600
C4—C5	1.391 (3)	C15—H15C	0.9600
C4—H4A	0.9300
O2i—Zn1—O2	115.11 (9)	C5—C6—H6A	119.7
O2i—Zn1—N1	110.57 (6)	C6—C7—C2	121.5 (2)
O2—Zn1—N1	96.45 (6)	C6—C7—H7A	119.3
O2i—Zn1—N1i	96.45 (6)	C2—C7—H7A	119.3
O2—Zn1—N1i	110.57 (6)	N1—C8—C9	128.41 (17)
N1—Zn1—N1i	128.79 (9)	N1—C8—H8A	115.8
C8—N1—C5	118.39 (15)	C9—C8—H8A	115.8
C8—N1—Zn1	119.45 (13)	C14—C9—C10	119.53 (19)
C5—N1—Zn1	122.05 (11)	C14—C9—C8	125.43 (16)
C13—O1—C15	117.05 (19)	C10—C9—C8	114.97 (18)
C14—O2—Zn1	125.29 (12)	C11—C10—C9	121.3 (2)
C2—C1—H1A	109.5	C11—C10—H10A	119.4
C2—C1—H1B	109.5	C9—C10—H10A	119.4
H1A—C1—H1B	109.5	C10—C11—C12	120.0 (2)
C2—C1—H1C	109.5	C10—C11—H11A	120.0
H1A—C1—H1C	109.5	C12—C11—H11A	120.0
H1B—C1—H1C	109.5	C13—C12—C11	120.4 (2)
C3—C2—C7	117.5 (2)	C13—C12—H12A	119.8
C3—C2—C1	121.5 (2)	C11—C12—H12A	119.8
C7—C2—C1	121.0 (2)	O1—C13—C12	124.2 (2)
C4—C3—C2	122.1 (2)	O1—C13—C14	114.43 (16)
C4—C3—H3A	118.9	C12—C13—C14	121.4 (2)
C2—C3—H3A	118.9	O2—C14—C9	124.19 (17)
C3—C4—C5	119.94 (19)	O2—C14—C13	118.47 (17)
C3—C4—H4A	120.0	C9—C14—C13	117.33 (16)
C5—C4—H4A	120.0	O1—C15—H15A	109.5
C6—C5—C4	118.24 (19)	O1—C15—H15B	109.5
C6—C5—N1	118.37 (17)	H15A—C15—H15B	109.5
C4—C5—N1	123.39 (17)	O1—C15—H15C	109.5
C7—C6—C5	120.6 (2)	H15A—C15—H15C	109.5
C7—C6—H6A	119.7	H15B—C15—H15C	109.5
O2i—Zn1—N1—C8	−111.17 (15)	C5—N1—C8—C9	178.22 (19)
O2—Zn1—N1—C8	8.73 (15)	Zn1—N1—C8—C9	−5.4 (3)
N1i—Zn1—N1—C8	131.72 (15)	N1—C8—C9—C14	−1.6 (3)
O2i—Zn1—N1—C5	65.06 (15)	N1—C8—C9—C10	−178.4 (2)
O2—Zn1—N1—C5	−175.04 (14)	C14—C9—C10—C11	−0.7 (4)
N1i—Zn1—N1—C5	−52.05 (13)	C8—C9—C10—C11	176.4 (2)
O2i—Zn1—O2—C14	107.71 (16)	C9—C10—C11—C12	1.0 (4)
N1—Zn1—O2—C14	−8.61 (16)	C10—C11—C12—C13	−0.2 (4)
N1i—Zn1—O2—C14	−144.32 (15)	C15—O1—C13—C12	8.0 (4)
C7—C2—C3—C4	−1.5 (4)	C15—O1—C13—C14	−172.3 (2)
C1—C2—C3—C4	178.9 (2)	C11—C12—C13—O1	178.7 (2)
C2—C3—C4—C5	0.4 (3)	C11—C12—C13—C14	−1.0 (4)
C3—C4—C5—C6	1.7 (3)	Zn1—O2—C14—C9	4.4 (3)
C3—C4—C5—N1	−178.54 (18)	Zn1—O2—C14—C13	−175.95 (14)
C8—N1—C5—C6	−151.95 (19)	C10—C9—C14—O2	179.16 (19)
Zn1—N1—C5—C6	31.8 (2)	C8—C9—C14—O2	2.4 (3)
C8—N1—C5—C4	28.3 (3)	C10—C9—C14—C13	−0.5 (3)
Zn1—N1—C5—C4	−147.93 (15)	C8—C9—C14—C13	−177.21 (19)
C4—C5—C6—C7	−2.8 (3)	O1—C13—C14—O2	1.9 (3)
N1—C5—C6—C7	177.5 (2)	C12—C13—C14—O2	−178.3 (2)
C5—C6—C7—C2	1.7 (4)	O1—C13—C14—C9	−178.41 (18)
C3—C2—C7—C6	0.5 (4)	C12—C13—C14—C9	1.3 (3)
C1—C2—C7—C6	−179.9 (3)