{(E)-2-[3-(Dimethyl­ammonio)propyl­iminometh­yl]phenolato}diiodidozinc(II)

Zhu, X.-W.; Yang, X.-Z.

doi:10.1107/S1600536808023659

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages m1090-m1091

doi:10.1107/S1600536808023659

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{(E)-2-[3-(Dimethylammonio)propyliminomethyl]phenolato}diiodidozinc(II)

Xue-Wen Zhu ^a ^* and Xu-Zhao Yang ^a

^aKey Laboratory of Surface and Interface Science of Henan, School of Materials and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: xuewen_zhu@126.com

(Received 25 July 2008; accepted 27 July 2008; online 31 July 2008)

The title complex, [ZnI₂(C₁₂H₁₈N₂O)], is a mononuclear zinc(II) compound derived from the zwitterionic form of the Schiff base (E)-2-[(3-dimethylaminopropylimino)methyl]phenol. The Zn^II atom is four-coordinated by the imine N and phenolate O atoms of the Schiff base ligand, and by two iodide ions in a tetrahedral coordination geometry. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For background to the chemistry of Schiff base complexes, see: Ali et al. (2008 ); Biswas et al. (2008 ); Chen et al. (2008 ); Darensbourg & Frantz (2007 ); Habibi et al. (2007 ); Kawamoto et al. (2008 ); Lipscomb & Sträter (1996 ); Tomat et al. (2007 ); Wu et al. (2008 ); Yuan et al. (2007 ). For related structures, see: Qiu (2006a ,b ); Wei et al. (2007 ); Zhu et al. (2007 ).

Experimental

Crystal data

[ZnI₂(C₁₂H₁₈N₂O)]
M_r = 525.45
Orthorhombic, P n a 2₁
a = 13.892 (3) Å
b = 16.640 (2) Å
c = 7.372 (3) Å
V = 1704.1 (8) Å³
Z = 4
Mo Kα radiation
μ = 5.06 mm⁻¹
T = 298 (2) K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.431, T_max = 0.463 (expected range = 0.375–0.402)
12154 measured reflections
3669 independent reflections
3271 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.100
S = 1.04
3669 reflections
165 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 1.82 e Å⁻³
Δρ_min = −0.47 e Å⁻³
Absolute structure: Flack (1983 ), 1660 Friedel pairs
Flack parameter: 0.00 (4)

Table 1
Selected geometric parameters (Å, °)

Zn1—O1	1.952 (4)
Zn1—N1	2.010 (6)
Zn1—I2	2.5550 (11)
Zn1—I1	2.5615 (11)

O1—Zn1—N1	94.3 (2)
O1—Zn1—I2	112.17 (16)
N1—Zn1—I2	113.02 (16)
O1—Zn1—I1	112.90 (16)
N1—Zn1—I1	106.74 (18)
I2—Zn1—I1	115.67 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.91	1.91	2.772 (8)	157
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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: 10.1107/S1600536808023659/sj2522sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023659/sj2522Isup2.hkl

checkCIF report

Comment top

Schiff bases have widely been used as versatile ligands in coordination chemistry (Biswas et al., 2008; Wu et al., 2008; Kawamoto et al., 2008; Ali et al., 2008; Habibi et al., 2007), and their metal complexes are of great interest in many fields (Chen et al., 2008; Yuan et al., 2007; Tomat et al., 2007; Darensbourg & Frantz, 2007). Zinc(II) is an important element in biological systems and functions as the active site of hydrolytic enzymes, such as carboxypeptidase and carbonic anhydrase where it is in a hard-donor coordination environment of nitrogen and oxygen ligands (Lipscomb & Sträter, 1996). In this paper, a new zinc(II) complex, (I), Fig. 1, of the Schiff base ligand (E)-2-[(3-dimethylaminopropylimino)methyl]phenol has been synthesized and structurally characterized.

The Zn^II atom in (I) is four-coordinated by the imine N and phenolate O atoms of the zwitterionic form of the Schiff base ligand, and by two I^- ions, in a tetrahedral coordination geometry. The coordinate bond lengths (Table 1) are typical and comparable to the corresponding values observed in other similar zinc(II) Schiff base complexes (Zhu et al., 2007; Wei et al., 2007; Qiu, 2006a,b).

In the crystal structure, molecules are linked through intermolecular N–H···O hydrogen bonds (Table 2), forming chains running along the b axis (Fig. 2).

Related literature top

For background to the chemistry of Schiff base complexes, see: Ali et al. (2008); Biswas et al. (2008); Chen et al. (2008); Darensbourg & Frantz (2007); Habibi et al. (2007); Kawamoto et al. (2008); Lipscomb & Sträter (1996); Tomat et al. (2007); Wu et al. (2008); Yuan et al. (2007). For related structures, see: Qiu (2006a,b); Wei et al. (2007); Zhu et al. (2007).

Experimental top

The Schiff base compound was prepared by the condensation of equimolar amounts of salicylaldehyde with N,N-dimethylpropane-1,3-diamine in a methanol solution. The complex was prepared by the following method. To an anhydrous methanol solution (5 ml) of ZnI₂ (31.9 mg, 0.1 mmol) was added a methanol solution (10 ml) of the Schiff base compound (20.6 mg, 0.1 mmol) with stirring. The mixture was stirred for 30 min at room temperature and filtered. Upon keeping the filtrate in air for a few days, colorless block-shaped crystals were formed at the bottom of the vessel on slow evaporation of the solvent.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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) with ellipsoids drawn at the 30% probability level.
	Fig. 2. The crystal packing of (I), viewed along the c axis.

{(E)-2-[3-(Dimethylammonio)propyliminomethyl]phenolato}diiodidozinc(II) top

Crystal data top

[ZnI₂(C₁₂H₁₈N₂O)]	F(000) = 992
M_r = 525.45	D_x = 2.048 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4125 reflections
a = 13.892 (3) Å	θ = 2.4–25.0°
b = 16.640 (2) Å	µ = 5.06 mm⁻¹
c = 7.372 (3) Å	T = 298 K
V = 1704.1 (8) Å³	Block, colorless
Z = 4	0.20 × 0.20 × 0.18 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3669 independent reflections
Radiation source: fine-focus sealed tube	3271 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −17→17
T_min = 0.431, T_max = 0.463	k = −20→21
12154 measured reflections	l = −9→9

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0426P)² + 0.9395P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3669 reflections	Δρ_max = 1.82 e Å⁻³
165 parameters	Δρ_min = −0.47 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1660 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (4)

Crystal data top

[ZnI₂(C₁₂H₁₈N₂O)]	V = 1704.1 (8) Å³
M_r = 525.45	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 13.892 (3) Å	µ = 5.06 mm⁻¹
b = 16.640 (2) Å	T = 298 K
c = 7.372 (3) Å	0.20 × 0.20 × 0.18 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3669 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3271 reflections with I > 2σ(I)
T_min = 0.431, T_max = 0.463	R_int = 0.048
12154 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.100	Δρ_max = 1.82 e Å⁻³
S = 1.04	Δρ_min = −0.47 e Å⁻³
3669 reflections	Absolute structure: Flack (1983), 1660 Friedel pairs
165 parameters	Absolute structure parameter: 0.00 (4)
1 restraint

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Zn1	0.75194 (6)	0.90239 (4)	0.72869 (14)	0.03631 (19)
I1	0.58993 (3)	0.92236 (3)	0.88834 (9)	0.04992 (15)
I2	0.89258 (4)	0.98333 (3)	0.85716 (9)	0.05741 (18)
N1	0.7294 (4)	0.9228 (3)	0.4634 (8)	0.0379 (13)
N2	0.8361 (5)	1.1716 (3)	0.3321 (11)	0.0544 (19)
H2A	0.7857	1.2052	0.3106	0.065*
O1	0.7847 (4)	0.7893 (3)	0.6946 (7)	0.0429 (12)
C1	0.8309 (5)	0.7664 (4)	0.5451 (11)	0.0385 (16)
C2	0.8869 (6)	0.6960 (5)	0.5496 (14)	0.053 (2)
H2	0.8923	0.6672	0.6573	0.063*
C3	0.9338 (6)	0.6691 (5)	0.396 (2)	0.070 (3)
H3	0.9722	0.6234	0.4030	0.084*
C4	0.9256 (7)	0.7066 (5)	0.2392 (16)	0.063 (3)
H4	0.9575	0.6865	0.1380	0.075*
C5	0.8701 (7)	0.7758 (5)	0.2225 (15)	0.063 (2)
H5	0.8653	0.8019	0.1113	0.075*
C6	0.8209 (5)	0.8061 (4)	0.3760 (13)	0.0422 (15)
C7	0.7648 (5)	0.8782 (4)	0.3445 (10)	0.0389 (16)
H7	0.7542	0.8926	0.2243	0.047*
C8	0.6691 (5)	0.9919 (4)	0.4056 (12)	0.0456 (19)
H8A	0.6074	0.9889	0.4667	0.055*
H8B	0.6574	0.9880	0.2761	0.055*
C9	0.7143 (6)	1.0712 (4)	0.4458 (11)	0.0459 (19)
H9A	0.7358	1.0721	0.5710	0.055*
H9B	0.6668	1.1134	0.4305	0.055*
C10	0.7992 (6)	1.0871 (4)	0.3217 (13)	0.049 (2)
H10A	0.8510	1.0505	0.3531	0.059*
H10B	0.7802	1.0758	0.1977	0.059*
C11	0.8730 (10)	1.1894 (6)	0.5117 (19)	0.100 (5)
H11A	0.9164	1.1476	0.5488	0.150*
H11B	0.8205	1.1926	0.5960	0.150*
H11C	0.9066	1.2398	0.5092	0.150*
C12	0.9089 (8)	1.1848 (6)	0.186 (2)	0.101 (5)
H12A	0.9269	1.2405	0.1834	0.151*
H12B	0.8819	1.1699	0.0711	0.151*
H12C	0.9648	1.1525	0.2099	0.151*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0426 (5)	0.0328 (3)	0.0335 (4)	0.0041 (3)	0.0026 (4)	0.0028 (3)
I1	0.0415 (3)	0.0491 (2)	0.0591 (3)	0.00396 (18)	0.0126 (3)	−0.0002 (3)
I2	0.0486 (3)	0.0603 (3)	0.0633 (4)	−0.0039 (2)	−0.0084 (3)	−0.0062 (3)
N1	0.037 (3)	0.042 (3)	0.035 (3)	−0.012 (2)	−0.001 (3)	−0.004 (3)
N2	0.048 (4)	0.029 (3)	0.086 (6)	0.005 (3)	−0.002 (4)	0.007 (3)
O1	0.052 (3)	0.032 (2)	0.045 (3)	0.008 (2)	0.007 (3)	0.006 (2)
C1	0.034 (4)	0.033 (3)	0.048 (5)	−0.008 (3)	0.005 (3)	−0.002 (3)
C2	0.055 (5)	0.040 (4)	0.063 (6)	0.008 (4)	0.016 (4)	0.005 (4)
C3	0.059 (5)	0.040 (4)	0.111 (9)	0.008 (4)	0.019 (7)	−0.003 (6)
C4	0.063 (6)	0.052 (5)	0.073 (7)	0.010 (4)	0.028 (5)	−0.016 (5)
C5	0.070 (6)	0.063 (5)	0.055 (6)	0.001 (4)	0.014 (5)	−0.012 (5)
C6	0.040 (4)	0.040 (3)	0.046 (4)	0.003 (3)	0.008 (4)	−0.004 (4)
C7	0.049 (4)	0.044 (3)	0.024 (4)	0.001 (3)	0.003 (3)	0.001 (3)
C8	0.041 (4)	0.045 (3)	0.051 (5)	0.001 (3)	−0.004 (4)	0.017 (4)
C9	0.051 (5)	0.039 (4)	0.047 (5)	0.016 (3)	−0.006 (4)	0.005 (3)
C10	0.051 (5)	0.027 (3)	0.070 (6)	0.005 (3)	0.005 (4)	0.006 (3)
C11	0.111 (10)	0.054 (6)	0.135 (11)	−0.023 (6)	−0.078 (9)	0.026 (6)
C12	0.074 (7)	0.052 (5)	0.177 (15)	0.007 (5)	0.051 (8)	0.028 (8)

Geometric parameters (Å, º) top

Zn1—O1	1.952 (4)	C5—C6	1.415 (12)
Zn1—N1	2.010 (6)	C5—H5	0.9300
Zn1—I2	2.5550 (11)	C6—C7	1.449 (9)
Zn1—I1	2.5615 (11)	C7—H7	0.9300
N1—C7	1.250 (9)	C8—C9	1.491 (10)
N1—C8	1.485 (9)	C8—H8A	0.9700
N2—C11	1.451 (14)	C8—H8B	0.9700
N2—C12	1.493 (15)	C9—C10	1.516 (12)
N2—C10	1.498 (8)	C9—H9A	0.9700
N2—H2A	0.9100	C9—H9B	0.9700
O1—C1	1.331 (9)	C10—H10A	0.9700
C1—C2	1.406 (10)	C10—H10B	0.9700
C1—C6	1.417 (12)	C11—H11A	0.9600
C2—C3	1.384 (15)	C11—H11B	0.9600
C2—H2	0.9300	C11—H11C	0.9600
C3—C4	1.317 (17)	C12—H12A	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C4—C5	1.392 (12)	C12—H12C	0.9600
C4—H4	0.9300

O1—Zn1—N1	94.3 (2)	N1—C7—C6	126.2 (7)
O1—Zn1—I2	112.17 (16)	N1—C7—H7	116.9
N1—Zn1—I2	113.02 (16)	C6—C7—H7	116.9
O1—Zn1—I1	112.90 (16)	N1—C8—C9	113.0 (6)
N1—Zn1—I1	106.74 (18)	N1—C8—H8A	109.0
I2—Zn1—I1	115.67 (4)	C9—C8—H8A	109.0
C7—N1—C8	118.8 (7)	N1—C8—H8B	109.0
C7—N1—Zn1	121.4 (5)	C9—C8—H8B	109.0
C8—N1—Zn1	119.9 (5)	H8A—C8—H8B	107.8
C11—N2—C12	112.8 (9)	C8—C9—C10	111.2 (6)
C11—N2—C10	111.1 (7)	C8—C9—H9A	109.4
C12—N2—C10	109.5 (8)	C10—C9—H9A	109.4
C11—N2—H2A	107.8	C8—C9—H9B	109.4
C12—N2—H2A	107.8	C10—C9—H9B	109.4
C10—N2—H2A	107.8	H9A—C9—H9B	108.0
C1—O1—Zn1	119.6 (4)	N2—C10—C9	113.5 (6)
O1—C1—C2	119.0 (7)	N2—C10—H10A	108.9
O1—C1—C6	123.2 (6)	C9—C10—H10A	108.9
C2—C1—C6	117.6 (7)	N2—C10—H10B	108.9
C3—C2—C1	120.7 (9)	C9—C10—H10B	108.9
C3—C2—H2	119.6	H10A—C10—H10B	107.7
C1—C2—H2	119.6	N2—C11—H11A	109.5
C4—C3—C2	121.6 (8)	N2—C11—H11B	109.5
C4—C3—H3	119.2	H11A—C11—H11B	109.5
C2—C3—H3	119.2	N2—C11—H11C	109.5
C3—C4—C5	121.2 (9)	H11A—C11—H11C	109.5
C3—C4—H4	119.4	H11B—C11—H11C	109.5
C5—C4—H4	119.4	N2—C12—H12A	109.5
C4—C5—C6	119.5 (10)	N2—C12—H12B	109.5
C4—C5—H5	120.3	H12A—C12—H12B	109.5
C6—C5—H5	120.3	N2—C12—H12C	109.5
C5—C6—C1	119.3 (7)	H12A—C12—H12C	109.5
C5—C6—C7	115.2 (8)	H12B—C12—H12C	109.5
C1—C6—C7	125.4 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.91	1.91	2.772 (8)	157

Symmetry code: (i) −x+3/2, y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[ZnI₂(C₁₂H₁₈N₂O)]
M_r	525.45
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	13.892 (3), 16.640 (2), 7.372 (3)
V (Å³)	1704.1 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.06
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.431, 0.463
No. of measured, independent and observed [I > 2σ(I)] reflections	12154, 3669, 3271
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.100, 1.04
No. of reflections	3669
No. of parameters	165
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.82, −0.47
Absolute structure	Flack (1983), 1660 Friedel pairs
Absolute structure parameter	0.00 (4)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Zn1—O1	1.952 (4)	Zn1—I2	2.5550 (11)
Zn1—N1	2.010 (6)	Zn1—I1	2.5615 (11)

O1—Zn1—N1	94.3 (2)	O1—Zn1—I1	112.90 (16)
O1—Zn1—I2	112.17 (16)	N1—Zn1—I1	106.74 (18)
N1—Zn1—I2	113.02 (16)	I2—Zn1—I1	115.67 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.91	1.91	2.772 (8)	157

Symmetry code: (i) −x+3/2, y+1/2, z−1/2.

References

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages m1090-m1091

doi:10.1107/S1600536808023659

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