Bis{2-[(2-furylmeth-yl)imino-meth-yl]-5-meth-oxy-phenolato-κN,O}zinc(II).

In the title complex, [Zn(C(13)H(12)NO(3))(2)], the Zn(II) ion is located on a twofold rotation axis and is coordinated by two bidentate Schiff base ligands in a distorted tetra-hedral environment. The complex mol-ecules are stacked in columns along the b axis through C-H⋯O hydrogen bonds.

Related literature

For the biological activity and applications of Zn(II) complexes, see: Csaszar et al. (1985 ▶); Greener et al. (1996 ▶); Gultneh et al. (1996 ▶); Aoki & Kimura (2004 ▶). For applications of furfuryl­amine derivatives, see: Camejo et al. (1992 ▶); Ledovskikh & Camejo (1993 ▶). For a related structure, see; Cai et al. (2010 ▶).

Experimental

Crystal data

[Zn(C13H12NO3)2]

M = 525.84

Monoclinic,

a = 27.210 (4) Å

b = 5.2244 (7) Å

c = 19.007 (3) Å

β = 119.507 (2)°

V = 2351.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.09 mm−1

T = 298 K

0.32 × 0.20 × 0.13 mm

Data collection

Bruker SMART CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.722, T max = 0.871

6855 measured reflections

2303 independent reflections

2062 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.128

S = 1.01

2303 reflections

160 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011536/is2670sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011536/is2670Isup2.hkl

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

[Zn(C13H12NO3)2]	F(000) = 1088
Mr = 525.84	Dx = 1.485 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2246 reflections
a = 27.210 (4) Å	θ = 2.5–23.7°
b = 5.2244 (7) Å	µ = 1.09 mm−1
c = 19.007 (3) Å	T = 298 K
β = 119.507 (2)°	Block, yellow
V = 2351.5 (5) Å3	0.32 × 0.20 × 0.13 mm
Z = 4

Bruker SMART CCD area detector diffractometer	2303 independent reflections
Radiation source: fine-focus sealed tube	2062 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −33→33
Tmin = 0.722, Tmax = 0.871	k = −6→6
6855 measured reflections	l = −23→20

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0784P)2 + 2.4971P] where P = (Fo2 + 2Fc2)/3
2303 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.64 e Å−3
1 restraint	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 > 2sigma(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	0.78566 (12)	0.2500	0.0427 (3)
N1	0.02638 (12)	0.5960 (6)	0.18435 (18)	0.0394 (7)
O1	0.06578 (11)	0.9989 (6)	0.30670 (18)	0.0549 (7)
O2	0.24426 (12)	1.3537 (7)	0.3745 (2)	0.0665 (9)
O3	−0.03914 (17)	0.7542 (6)	0.0242 (2)	0.0729 (10)
C1	0.11535 (15)	0.8329 (7)	0.2413 (2)	0.0403 (8)
C2	0.10942 (14)	1.0010 (7)	0.2954 (2)	0.0402 (8)
C3	0.15270 (16)	1.1795 (8)	0.3399 (3)	0.0465 (9)
H3	0.1490	1.2918	0.3750	0.056*
C4	0.20061 (16)	1.1895 (8)	0.3319 (3)	0.0489 (9)
C5	0.20638 (16)	1.0283 (9)	0.2781 (3)	0.0550 (10)
H5	0.2382	1.0385	0.2720	0.066*
C6	0.16505 (16)	0.8560 (9)	0.2348 (3)	0.0505 (10)
H6	0.1694	0.7483	0.1993	0.061*
C7	0.2397 (2)	1.5304 (9)	0.4279 (3)	0.0675 (13)
H7A	0.2080	1.6411	0.3976	0.101*
H7B	0.2736	1.6309	0.4545	0.101*
H7C	0.2345	1.4386	0.4675	0.101*
C8	0.07515 (15)	0.6467 (7)	0.1911 (2)	0.0417 (8)
H8	0.0851	0.5491	0.1591	0.050*
C9	−0.00946 (17)	0.4112 (8)	0.1224 (2)	0.0508 (9)
H9A	−0.0260	0.2943	0.1446	0.061*
H9B	0.0134	0.3118	0.1061	0.061*
C10	−0.05497 (17)	0.5418 (8)	0.0510 (2)	0.0517 (10)
C11	−0.1095 (2)	0.4911 (15)	0.0025 (3)	0.0929 (17)
H11	−0.1303	0.3563	0.0065	0.111*
C12	−0.1294 (3)	0.6947 (16)	−0.0583 (4)	0.102 (2)
H12	−0.1661	0.7157	−0.1007	0.123*
C13	−0.0861 (3)	0.8419 (15)	−0.0423 (3)	0.103 (2)
H13	−0.0874	0.9855	−0.0721	0.123*

	U11	U22	U33	U12	U13	U23
Zn1	0.0333 (4)	0.0510 (4)	0.0525 (4)	0.000	0.0278 (3)	0.000
N1	0.0346 (15)	0.0452 (16)	0.0426 (16)	0.0013 (13)	0.0222 (13)	0.0020 (13)
O1	0.0396 (15)	0.0674 (18)	0.0709 (18)	−0.0102 (13)	0.0372 (14)	−0.0200 (15)
O2	0.0414 (16)	0.070 (2)	0.083 (2)	−0.0157 (14)	0.0268 (16)	−0.0085 (18)
O3	0.079 (2)	0.070 (2)	0.064 (2)	0.0066 (17)	0.0316 (19)	0.0094 (16)
C1	0.0326 (18)	0.047 (2)	0.045 (2)	0.0031 (15)	0.0226 (16)	0.0047 (16)
C2	0.0301 (17)	0.0457 (19)	0.047 (2)	0.0029 (14)	0.0205 (15)	0.0023 (16)
C3	0.038 (2)	0.047 (2)	0.054 (2)	−0.0002 (16)	0.0232 (18)	−0.0007 (17)
C4	0.0342 (19)	0.052 (2)	0.056 (2)	−0.0027 (16)	0.0188 (18)	0.0068 (18)
C5	0.0336 (19)	0.074 (3)	0.066 (3)	0.0003 (18)	0.0304 (19)	0.005 (2)
C6	0.037 (2)	0.065 (3)	0.057 (2)	0.0034 (18)	0.0289 (18)	−0.002 (2)
C7	0.059 (3)	0.060 (3)	0.068 (3)	−0.018 (2)	0.019 (2)	−0.003 (2)
C8	0.0398 (19)	0.047 (2)	0.044 (2)	0.0051 (15)	0.0252 (17)	0.0000 (16)
C9	0.052 (2)	0.045 (2)	0.060 (2)	−0.0084 (18)	0.031 (2)	−0.0046 (19)
C10	0.043 (2)	0.065 (3)	0.050 (2)	−0.0058 (18)	0.0245 (18)	−0.014 (2)
C11	0.050 (3)	0.155 (5)	0.079 (3)	−0.021 (3)	0.036 (3)	−0.049 (3)
C12	0.064 (4)	0.167 (7)	0.056 (3)	0.042 (4)	0.015 (3)	−0.015 (3)
C13	0.119 (6)	0.113 (5)	0.055 (3)	0.052 (5)	0.027 (4)	0.014 (3)

Zn1—O1i	1.925 (3)	C4—C5	1.391 (6)
Zn1—O1	1.925 (3)	C5—C6	1.357 (6)
Zn1—N1	1.984 (3)	C5—H5	0.9300
Zn1—N1i	1.984 (3)	C6—H6	0.9300
N1—C8	1.296 (4)	C7—H7A	0.9600
N1—C9	1.463 (5)	C7—H7B	0.9600
O1—C2	1.306 (4)	C7—H7C	0.9600
O2—C4	1.362 (5)	C8—H8	0.9300
O2—C7	1.422 (6)	C9—C10	1.479 (6)
O3—C13	1.360 (7)	C9—H9A	0.9700
O3—C10	1.375 (5)	C9—H9B	0.9700
C1—C2	1.422 (5)	C10—C11	1.332 (6)
C1—C6	1.422 (5)	C11—C12	1.465 (10)
C1—C8	1.423 (5)	C11—H11	0.9300
C2—C3	1.411 (5)	C12—C13	1.311 (11)
C3—C4	1.386 (6)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
O1i—Zn1—O1	109.27 (18)	C1—C6—H6	118.6
O1i—Zn1—N1	117.49 (12)	O2—C7—H7A	109.5
O1—Zn1—N1	96.69 (11)	O2—C7—H7B	109.5
O1i—Zn1—N1i	96.69 (11)	H7A—C7—H7B	109.5
O1—Zn1—N1i	117.49 (12)	O2—C7—H7C	109.5
N1—Zn1—N1i	120.08 (18)	H7A—C7—H7C	109.5
C8—N1—C9	117.3 (3)	H7B—C7—H7C	109.5
C8—N1—Zn1	120.4 (3)	N1—C8—C1	128.1 (3)
C9—N1—Zn1	122.1 (2)	N1—C8—H8	115.9
C2—O1—Zn1	125.6 (2)	C1—C8—H8	115.9
C4—O2—C7	118.4 (3)	N1—C9—C10	111.1 (3)
C13—O3—C10	107.1 (5)	N1—C9—H9A	109.4
C2—C1—C6	117.5 (3)	C10—C9—H9A	109.4
C2—C1—C8	125.7 (3)	N1—C9—H9B	109.4
C6—C1—C8	116.7 (3)	C10—C9—H9B	109.4
O1—C2—C3	117.7 (3)	H9A—C9—H9B	108.0
O1—C2—C1	123.4 (3)	C11—C10—O3	110.5 (5)
C3—C2—C1	118.9 (3)	C11—C10—C9	133.4 (5)
C4—C3—C2	120.8 (4)	O3—C10—C9	116.0 (4)
C4—C3—H3	119.6	C10—C11—C12	104.7 (6)
C2—C3—H3	119.6	C10—C11—H11	127.6
O2—C4—C3	123.4 (4)	C12—C11—H11	127.6
O2—C4—C5	115.9 (4)	C13—C12—C11	107.5 (5)
C3—C4—C5	120.7 (4)	C13—C12—H12	126.2
C6—C5—C4	119.2 (3)	C11—C12—H12	126.2
C6—C5—H5	120.4	C12—C13—O3	110.1 (7)
C4—C5—H5	120.4	C12—C13—H13	124.9
C5—C6—C1	122.9 (4)	O3—C13—H13	124.9
C5—C6—H6	118.6

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1ii	0.97	2.32	3.292 (6)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1i	0.97	2.32	3.292 (6)	177

Symmetry code: (i) .