Bis[2-(cyclo­propyl­imino­meth­yl)-5-methoxy­phenolato]zinc(II)

Bai, L.-M.

doi:10.1107/S1600536810013541

metal-organic compounds

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Volume 66| Part 5| May 2010| Page m531

https://doi.org/10.1107/S1600536810013541

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Bis[2-(cyclopropyliminomethyl)-5-methoxyphenolato]zinc(II)

Li-Ming Bai ^a ^*

^aCollege of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar 161006, People's Republic of China
^*Correspondence e-mail: bailiming68@yahoo.com.cn

(Received 12 April 2010; accepted 12 April 2010; online 17 April 2010)

In the title complex, [Zn(C₁₁H₁₂NO₂)₂], the Zn²⁺ ion (site symmetry 2) is coordinated by two N,O-bidentate Schiff base ligands, generating a tetrahedral ZnO₂N₂ 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_r = 445.80
Orthorhombic, P b c n
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.126
S = 1.02
2424 reflections
133 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

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) $[-x+1, y, -z+{\script{3\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810013541/hb5404sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810013541/hb5404Isup2.hkl

checkCIF report

Comment top

Zinc complexes with Schiff bases have attracted much attention in coordination chemistry and biological chemistry (Maxim et al., 2008; Ali et al., 2004; Keypour et al., 2009; Osowole et al., 2008; Kulandaisamy & Thomas, 2008). In the present paper, the title zinc(II) complex with the Schiff base 2-(cyclopropyliminomethyl)-5-methoxyphenol has been prepared and characterized by X-ray diffraction.

The title zinc complex, Fig. 1, possesses crystallographic two-fold rotation axis symmetry. The Zn atom is coordinated by two phenolic oxygen and two imino N atoms from two Schiff base ligands, generating a tetrahedral geometry. The bond lengths and angles (Table 1) around the Zn atom are typical and comparable to those in other Schiff base zinc(II) complexes (Wei et al., 2007; Li & Zhang, 2005; Parvez & Birdsall, 1990; Cui et al., 2009).

Related literature top

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 top

2-Hydroxy-4-methoxybenzaldehyde (0.152 g, 1 mmol) and cyclopropylamine (0.057 g, 1 mmol) were mixed and refluxed in a methanol solution (50 ml) with stirring for 1 h. To the above solution was added a methanol solution (10 ml) of Zn(CH₃COO)₂.2H₂O (0.110 g, 0.5 mmol). The mixture was stirred at reflux for another 1 h, and cooled to room temperature. After keeping the solution in air for a few days, colourless blocks of (I) were formed.

Structure description top

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).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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), showing 30% probability displacement ellipsoids. Unlabeled atoms are at the symmetry position 1 - x, y, 3/2 - z.

Bis[2-(cyclopropyliminomethyl)-5-methoxyphenolato]zinc(II) top

Crystal data top

[Zn(C₁₁H₁₂NO₂)₂]	F(000) = 928
M_r = 445.80	D_x = 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

Data collection top

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

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0608P)² + 0.4149P] where P = (F_o² + 2F_c²)/3
2424 reflections	(Δ/σ)_max < 0.001
133 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Zn(C₁₁H₁₂NO₂)₂]	V = 2130.9 (7) Å³
M_r = 445.80	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 8.9646 (18) Å	µ = 1.18 mm⁻¹
b = 10.628 (2) Å	T = 298 K
c = 22.366 (4) Å	0.23 × 0.21 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	2424 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1492 reflections with I > 2σ(I)
T_min = 0.773, T_max = 0.798	R_int = 0.050
12146 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.02	Δρ_max = 0.43 e Å⁻³
2424 reflections	Δρ_min = −0.31 e Å⁻³
133 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Symmetry code: (i) −x+1, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₁H₁₂NO₂)₂]
M_r	445.80
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	8.9646 (18), 10.628 (2), 22.366 (4)
V (Å³)	2130.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.18
Crystal size (mm)	0.23 × 0.21 × 0.20

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.773, 0.798
No. of measured, independent and observed [I > 2σ(I)] reflections	12146, 2424, 1492
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.126, 1.02
No. of reflections	2424
No. of parameters	133
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.31

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Zn1—O1	1.9169 (19)	Zn1—N1	2.017 (3)

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

Symmetry code: (i) −x+1, y, −z+3/2.

Acknowledgements

The author acknowledges Qiqihar University for funding this work.

References

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