Bis[2-(cyclo-propyl-imino-meth-yl)-5-methoxy-phenolato]zinc(II).

In the title complex, [Zn(C(11)H(12)NO(2))(2)], the Zn(2+) ion (site symmetry 2) is coordinated by two N,O-bidentate Schiff base ligands, generating a tetra-hedral ZnO(2)N(2) geometry for the metal ion.

Related literature

For background to zinc complexes with Schiff bases, see: Maxim et al. (2008 ▶); Ali et al. (2004 ▶); Keypour et al. (2009 ▶); Osowole et al. (2008 ▶); Kulandaisamy & Thomas (2008 ▶). For related structures, see: Wei et al. (2007 ▶); Li & Zhang (2005 ▶); Parvez & Birdsall (1990 ▶); Cui et al. (2009 ▶).

Experimental

Crystal data

[Zn(C11H12NO2)2]

M = 445.80

Orthorhombic,

a = 8.9646 (18) Å

b = 10.628 (2) Å

c = 22.366 (4) Å

V = 2130.9 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.18 mm−1

T = 298 K

0.23 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.773, T max = 0.798

12146 measured reflections

2424 independent reflections

1492 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.126

S = 1.02

2424 reflections

133 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536810013541/hb5404sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013541/hb5404Isup2.hkl

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

[Zn(C11H12NO2)2]	F(000) = 928
Mr = 445.80	Dx = 1.390 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 1989 reflections
a = 8.9646 (18) Å	θ = 2.7–24.5°
b = 10.628 (2) Å	µ = 1.18 mm−1
c = 22.366 (4) Å	T = 298 K
V = 2130.9 (7) Å3	Block, colourless
Z = 4	0.23 × 0.21 × 0.20 mm

Bruker SMART CCD diffractometer	2424 independent reflections
Radiation source: fine-focus sealed tube	1492 reflections with I > 2σ(I)
graphite	Rint = 0.050
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→11
Tmin = 0.773, Tmax = 0.798	k = −12→13
12146 measured reflections	l = −28→28

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0608P)2 + 0.4149P] where P = (Fo2 + 2Fc2)/3
2424 reflections	(Δ/σ)max < 0.001
133 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.5000	0.55230 (4)	0.7500	0.0614 (2)
N1	0.3162 (3)	0.4471 (2)	0.73578 (11)	0.0623 (7)
O1	0.4246 (2)	0.64630 (17)	0.81662 (9)	0.0670 (6)
O2	0.1210 (2)	0.7046 (2)	0.98928 (9)	0.0731 (6)
C1	0.2075 (3)	0.5152 (2)	0.83071 (12)	0.0514 (7)
C2	0.3079 (3)	0.6121 (2)	0.84814 (12)	0.0516 (7)
C3	0.2785 (3)	0.6755 (2)	0.90190 (12)	0.0552 (7)
H3	0.3418	0.7402	0.9139	0.066*
C4	0.1583 (3)	0.6445 (3)	0.93745 (12)	0.0545 (7)
C5	0.0621 (4)	0.5468 (3)	0.92121 (13)	0.0585 (7)
H5	−0.0177	0.5243	0.9455	0.070*
C6	0.0882 (3)	0.4853 (3)	0.86889 (13)	0.0569 (7)
H6	0.0240	0.4206	0.8579	0.068*
C7	0.2158 (4)	0.4431 (2)	0.77678 (15)	0.0597 (7)
H7	0.1386	0.3860	0.7706	0.072*
C8	0.2943 (4)	0.3637 (4)	0.68479 (16)	0.0864 (10)
H8	0.2062	0.3092	0.6868	0.104*
C9	0.4218 (5)	0.3109 (5)	0.6553 (2)	0.1302 (19)
H9A	0.4138	0.2255	0.6403	0.156*
H9B	0.5198	0.3341	0.6700	0.156*
C10	0.3341 (6)	0.4067 (5)	0.6265 (2)	0.1273 (17)
H10A	0.3771	0.4901	0.6230	0.153*
H10B	0.2711	0.3815	0.5933	0.153*
C11	0.1961 (5)	0.8193 (3)	1.00303 (15)	0.0968 (12)
H11A	0.3005	0.8029	1.0085	0.145*
H11B	0.1555	0.8543	1.0391	0.145*
H11C	0.1828	0.8778	0.9708	0.145*

	U11	U22	U33	U12	U13	U23
Zn1	0.0615 (4)	0.0490 (3)	0.0737 (4)	0.000	0.0197 (2)	0.000
N1	0.0615 (17)	0.0554 (14)	0.0701 (17)	0.0017 (12)	0.0063 (12)	−0.0116 (12)
O1	0.0642 (13)	0.0551 (11)	0.0817 (14)	−0.0132 (10)	0.0280 (11)	−0.0105 (10)
O2	0.0773 (15)	0.0828 (15)	0.0593 (13)	−0.0106 (12)	0.0155 (10)	−0.0056 (11)
C1	0.0463 (16)	0.0465 (14)	0.0613 (17)	0.0000 (12)	0.0041 (13)	0.0014 (13)
C2	0.0491 (16)	0.0423 (14)	0.0636 (17)	0.0024 (12)	0.0075 (13)	0.0035 (13)
C3	0.0554 (17)	0.0466 (15)	0.0634 (17)	−0.0047 (13)	0.0062 (13)	−0.0015 (13)
C4	0.0557 (17)	0.0542 (16)	0.0537 (16)	0.0038 (13)	0.0006 (13)	0.0056 (13)
C5	0.0490 (16)	0.0639 (18)	0.0625 (18)	−0.0016 (14)	0.0079 (14)	0.0116 (15)
C6	0.0468 (17)	0.0561 (17)	0.0677 (19)	−0.0050 (13)	0.0014 (13)	0.0055 (14)
C7	0.0516 (18)	0.0504 (16)	0.0771 (19)	−0.0014 (14)	0.0008 (16)	−0.0037 (15)
C8	0.074 (2)	0.102 (3)	0.083 (2)	0.007 (2)	0.0097 (19)	−0.021 (2)
C9	0.078 (3)	0.156 (4)	0.157 (4)	0.030 (3)	−0.009 (3)	−0.095 (4)
C10	0.127 (4)	0.164 (5)	0.091 (3)	−0.015 (4)	0.004 (3)	−0.027 (3)
C11	0.113 (3)	0.097 (3)	0.080 (3)	−0.024 (2)	0.021 (2)	−0.031 (2)

Zn1—O1	1.9169 (19)	C5—C6	1.360 (4)
Zn1—O1i	1.9169 (19)	C5—H5	0.9300
Zn1—N1i	2.017 (3)	C6—H6	0.9300
Zn1—N1	2.017 (3)	C7—H7	0.9300
N1—C7	1.286 (4)	C8—C10	1.427 (5)
N1—C8	1.458 (4)	C8—C9	1.434 (5)
O1—C2	1.313 (3)	C8—H8	0.9800
O2—C4	1.366 (3)	C9—C10	1.439 (7)
O2—C11	1.426 (4)	C9—H9A	0.9700
C1—C6	1.405 (4)	C9—H9B	0.9700
C1—C2	1.422 (4)	C10—H10A	0.9700
C1—C7	1.431 (4)	C10—H10B	0.9700
C2—C3	1.403 (4)	C11—H11A	0.9600
C3—C4	1.380 (4)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
C4—C5	1.398 (4)
O1—Zn1—O1i	117.19 (11)	C1—C6—H6	118.5
O1—Zn1—N1i	117.02 (10)	N1—C7—C1	128.3 (3)
O1i—Zn1—N1i	97.10 (9)	N1—C7—H7	115.9
O1—Zn1—N1	97.10 (9)	C1—C7—H7	115.9
O1i—Zn1—N1	117.02 (10)	C10—C8—C9	60.4 (3)
N1i—Zn1—N1	112.64 (14)	C10—C8—N1	119.1 (4)
C7—N1—C8	116.3 (3)	C9—C8—N1	119.4 (3)
C7—N1—Zn1	118.6 (2)	C10—C8—H8	115.6
C8—N1—Zn1	124.8 (2)	C9—C8—H8	115.6
C2—O1—Zn1	123.65 (17)	N1—C8—H8	115.6
C4—O2—C11	117.9 (2)	C8—C9—C10	59.6 (3)
C6—C1—C2	118.6 (3)	C8—C9—H9A	117.8
C6—C1—C7	115.5 (3)	C10—C9—H9A	117.8
C2—C1—C7	125.9 (3)	C8—C9—H9B	117.8
O1—C2—C3	118.5 (2)	C10—C9—H9B	117.8
O1—C2—C1	123.9 (2)	H9A—C9—H9B	115.0
C3—C2—C1	117.7 (2)	C8—C10—C9	60.0 (3)
C4—C3—C2	121.7 (3)	C8—C10—H10A	117.8
C4—C3—H3	119.1	C9—C10—H10A	117.8
C2—C3—H3	119.1	C8—C10—H10B	117.8
O2—C4—C3	124.7 (3)	C9—C10—H10B	117.8
O2—C4—C5	114.7 (3)	H10A—C10—H10B	114.9
C3—C4—C5	120.7 (3)	O2—C11—H11A	109.5
C6—C5—C4	118.3 (3)	O2—C11—H11B	109.5
C6—C5—H5	120.8	H11A—C11—H11B	109.5
C4—C5—H5	120.8	O2—C11—H11C	109.5
C5—C6—C1	123.1 (3)	H11A—C11—H11C	109.5
C5—C6—H6	118.5	H11B—C11—H11C	109.5

Zn1—O1	1.9169 (19)
Zn1—N1	2.017 (3)

O1—Zn1—O1i	117.19 (11)
O1—Zn1—N1i	117.02 (10)
O1—Zn1—N1	97.10 (9)

Symmetry code: (i) .