Dibromido{(E)-2-eth­oxy-6-[3-(methyl­ammonio)propyl­iminometh­yl]phenol­ato}zinc(II)

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

doi:10.1107/S1600536808023672

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages m1092-m1093

doi:10.1107/S1600536808023672

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Dibromido{(E)-2-ethoxy-6-[3-(methylammonio)propyliminomethyl]phenolato}zinc(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, [ZnBr₂(C₁₃H₂₀N₂O₂)], is a mononuclear zinc(II) compound derived from the zwitterionic form of the Schiff base (E)-2-ethoxy-6-((3-(methylamino)propylimino)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 bromide ions, in a tetrahedral coordination geometry. Adjacent 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 the 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 (2006 ); Wei et al. (2007 ); Zhu et al. (2007 ).

Experimental

Crystal data

[ZnBr₂(C₁₃H₂₀N₂O₂)]
M_r = 461.50
Monoclinic, C 2/c
a = 17.884 (3) Å
b = 14.374 (2) Å
c = 14.992 (2) Å
β = 114.482 (3)°
V = 3507.4 (9) Å³
Z = 8
Mo Kα radiation
μ = 5.96 mm⁻¹
T = 298 (2) K
0.23 × 0.21 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.341, T_max = 0.367 (expected range = 0.265–0.286)
14138 measured reflections
3787 independent reflections
1974 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.222
S = 1.00
3787 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 1.12 e Å⁻³
Δρ_min = −0.90 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—O1	1.958 (5)
Zn1—N1	2.014 (6)
Zn1—Br1	2.3429 (16)
Zn1—Br2	2.4046 (18)

O1—Zn1—N1	95.3 (2)
O1—Zn1—Br1	115.26 (16)
N1—Zn1—Br1	113.83 (19)
O1—Zn1—Br2	113.02 (17)
N1—Zn1—Br2	113.09 (19)
Br1—Zn1—Br2	106.38 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O1ⁱ	0.90	1.84	2.697 (8)	158
N2—H2B⋯O2ⁱ	0.90	2.40	3.005 (8)	124
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536808023672/sj2525sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023672/sj2525Isup2.hkl

checkCIF report

Comment top

Schiff bases have been widely 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, 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, with the Schiff base ligand 2-ethoxy-6-[(3-methylaminopropylimino)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 Br^- 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, 2006).

In the crystal structure, adjacent 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 the 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 (2006); Wei et al. (2007); Zhu et al. (2007).

Experimental top

The Schiff base compound was prepared by the condensation of equimolar amounts of 3-ethoxysalicylaldehyde with N-methylpropane-1,3-diamine in a methanol solution. The complex was prepared by the following method. To an anhydrous methanol solution (5 ml) of ZnBr₂ (22.5 mg, 0.1 mmol) was added a methanol solution (10 ml) of the Schiff base compound (23.6 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.

Dibromido{(E)-2-ethoxy-6-[3- (methylammonio)propyliminomethyl]phenolato}zinc(II) top

Crystal data top

[ZnBr₂(C₁₃H₂₀N₂O₂)]	F(000) = 1824
M_r = 461.50	D_x = 1.748 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1842 reflections
a = 17.884 (3) Å	θ = 2.4–24.1°
b = 14.374 (2) Å	µ = 5.96 mm⁻¹
c = 14.992 (2) Å	T = 298 K
β = 114.482 (3)°	Block, colorless
V = 3507.4 (9) Å³	0.23 × 0.21 × 0.21 mm
Z = 8

Data collection top

Bruker APEXII CCD area-detector diffractometer	3787 independent reflections
Radiation source: fine-focus sealed tube	1974 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −22→22
T_min = 0.341, T_max = 0.368	k = −18→18
14138 measured reflections	l = −18→18

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.222	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1251P)²] where P = (F_o² + 2F_c²)/3
3787 reflections	(Δ/σ)_max = 0.001
183 parameters	Δρ_max = 1.12 e Å⁻³
0 restraints	Δρ_min = −0.90 e Å⁻³

Crystal data top

[ZnBr₂(C₁₃H₂₀N₂O₂)]	V = 3507.4 (9) Å³
M_r = 461.50	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 17.884 (3) Å	µ = 5.96 mm⁻¹
b = 14.374 (2) Å	T = 298 K
c = 14.992 (2) Å	0.23 × 0.21 × 0.21 mm
β = 114.482 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3787 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1974 reflections with I > 2σ(I)
T_min = 0.341, T_max = 0.368	R_int = 0.068
14138 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.222	H-atom parameters constrained
S = 1.00	Δρ_max = 1.12 e Å⁻³
3787 reflections	Δρ_min = −0.90 e Å⁻³
183 parameters

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	0.27393 (5)	0.33839 (6)	0.31911 (7)	0.0412 (3)
Br1	0.41500 (7)	0.37049 (9)	0.38443 (10)	0.0911 (5)
Br2	0.22492 (8)	0.35250 (9)	0.14417 (9)	0.0842 (4)
O1	0.2106 (3)	0.4129 (3)	0.3728 (4)	0.0457 (13)
O2	0.1034 (3)	0.5348 (4)	0.3750 (4)	0.0524 (15)
N1	0.2463 (4)	0.2150 (4)	0.3615 (5)	0.0435 (15)
N2	0.2234 (4)	0.0849 (4)	0.0895 (5)	0.0506 (17)
H2A	0.2508	0.1333	0.0793	0.061*
H2B	0.2536	0.0335	0.0945	0.061*
C1	0.1272 (5)	0.2825 (6)	0.3792 (6)	0.049 (2)
C2	0.1426 (4)	0.3790 (5)	0.3754 (5)	0.0394 (17)
C3	0.0835 (5)	0.4402 (6)	0.3797 (5)	0.047 (2)
C4	0.0121 (5)	0.4091 (8)	0.3825 (6)	0.065 (3)
H4	−0.0272	0.4517	0.3819	0.078*
C5	−0.0022 (6)	0.3135 (8)	0.3860 (7)	0.074 (3)
H5	−0.0509	0.2930	0.3879	0.089*
C6	0.0554 (6)	0.2503 (8)	0.3869 (7)	0.068 (3)
H6	0.0473	0.1870	0.3924	0.082*
C7	0.1826 (6)	0.2104 (5)	0.3813 (6)	0.055 (2)
H7	0.1713	0.1520	0.3995	0.066*
C8	0.2915 (6)	0.1308 (6)	0.3638 (7)	0.057 (2)
H8A	0.2641	0.0783	0.3781	0.069*
H8B	0.3462	0.1354	0.4162	0.069*
C9	0.2982 (5)	0.1139 (6)	0.2700 (6)	0.055 (2)
H9A	0.3320	0.0593	0.2767	0.067*
H9B	0.3253	0.1665	0.2557	0.067*
C10	0.2170 (5)	0.0998 (6)	0.1873 (7)	0.057 (2)
H10A	0.1828	0.1536	0.1818	0.068*
H10B	0.1906	0.0461	0.2009	0.068*
C11	0.1458 (5)	0.0750 (7)	0.0041 (7)	0.065 (3)
H11A	0.1211	0.0166	0.0073	0.097*
H11B	0.1554	0.0771	−0.0543	0.097*
H11C	0.1097	0.1249	0.0029	0.097*
C12	0.0459 (6)	0.6012 (7)	0.3834 (7)	0.065 (3)
H12A	0.0413	0.5924	0.4450	0.079*
H12B	−0.0079	0.5922	0.3304	0.079*
C13	0.0754 (6)	0.6948 (8)	0.3788 (8)	0.084 (4)
H13A	0.1295	0.7025	0.4299	0.127*
H13B	0.0389	0.7395	0.3872	0.127*
H13C	0.0771	0.7041	0.3163	0.127*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0429 (5)	0.0361 (5)	0.0501 (6)	0.0014 (4)	0.0248 (4)	−0.0029 (4)
Br1	0.0580 (7)	0.0846 (8)	0.1261 (11)	0.0068 (5)	0.0335 (7)	−0.0125 (7)
Br2	0.0864 (8)	0.0953 (9)	0.0692 (8)	−0.0150 (6)	0.0305 (6)	0.0043 (6)
O1	0.042 (3)	0.036 (3)	0.071 (4)	0.001 (2)	0.034 (3)	−0.006 (3)
O2	0.046 (3)	0.061 (4)	0.051 (4)	0.019 (3)	0.021 (3)	−0.007 (3)
N1	0.049 (4)	0.038 (4)	0.042 (4)	0.000 (3)	0.017 (3)	−0.001 (3)
N2	0.050 (4)	0.035 (4)	0.061 (5)	0.005 (3)	0.018 (4)	0.006 (3)
C1	0.046 (5)	0.064 (6)	0.041 (5)	−0.017 (4)	0.022 (4)	−0.006 (4)
C2	0.040 (4)	0.046 (4)	0.030 (4)	0.000 (3)	0.012 (3)	−0.002 (3)
C3	0.044 (5)	0.067 (6)	0.032 (5)	0.012 (4)	0.017 (4)	0.001 (4)
C4	0.039 (5)	0.113 (9)	0.050 (6)	0.013 (5)	0.026 (4)	0.012 (5)
C5	0.057 (6)	0.103 (9)	0.069 (7)	−0.030 (6)	0.033 (5)	−0.011 (6)
C6	0.066 (6)	0.085 (7)	0.066 (7)	−0.013 (6)	0.039 (6)	−0.002 (6)
C7	0.084 (7)	0.029 (4)	0.053 (6)	−0.005 (4)	0.030 (5)	−0.006 (4)
C8	0.078 (6)	0.030 (4)	0.057 (6)	0.009 (4)	0.021 (5)	0.008 (4)
C9	0.051 (5)	0.042 (5)	0.061 (6)	0.002 (4)	0.012 (4)	−0.019 (4)
C10	0.042 (5)	0.043 (5)	0.078 (7)	−0.001 (4)	0.018 (5)	−0.014 (5)
C11	0.059 (6)	0.065 (6)	0.064 (6)	−0.005 (5)	0.019 (5)	0.010 (5)
C12	0.070 (6)	0.078 (7)	0.055 (6)	0.038 (5)	0.032 (5)	0.006 (5)
C13	0.084 (7)	0.074 (7)	0.071 (7)	0.038 (6)	0.007 (6)	−0.024 (6)

Geometric parameters (Å, º) top

Zn1—O1	1.958 (5)	C5—H5	0.9300
Zn1—N1	2.014 (6)	C6—H6	0.9300
Zn1—Br1	2.3429 (16)	C7—H7	0.9300
Zn1—Br2	2.4046 (18)	C8—C9	1.480 (12)
O1—C2	1.325 (8)	C8—H8A	0.9700
O2—C3	1.414 (11)	C8—H8B	0.9700
O2—C12	1.446 (9)	C9—C10	1.481 (11)
N1—C7	1.293 (11)	C9—H9A	0.9700
N1—C8	1.447 (10)	C9—H9B	0.9700
N2—C11	1.453 (10)	C10—H10A	0.9700
N2—C10	1.532 (11)	C10—H10B	0.9700
N2—H2A	0.9000	C11—H11A	0.9600
N2—H2B	0.9000	C11—H11B	0.9600
C1—C6	1.414 (12)	C11—H11C	0.9600
C1—C2	1.420 (11)	C12—C13	1.456 (15)
C1—C7	1.423 (12)	C12—H12A	0.9700
C2—C3	1.396 (11)	C12—H12B	0.9700
C3—C4	1.370 (12)	C13—H13A	0.9600
C4—C5	1.403 (15)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C5—C6	1.369 (14)

O1—Zn1—N1	95.3 (2)	C1—C7—H7	115.5
O1—Zn1—Br1	115.26 (16)	N1—C8—C9	112.2 (7)
N1—Zn1—Br1	113.83 (19)	N1—C8—H8A	109.2
O1—Zn1—Br2	113.02 (17)	C9—C8—H8A	109.2
N1—Zn1—Br2	113.09 (19)	N1—C8—H8B	109.2
Br1—Zn1—Br2	106.38 (6)	C9—C8—H8B	109.2
C2—O1—Zn1	120.3 (4)	H8A—C8—H8B	107.9
C3—O2—C12	115.4 (7)	C8—C9—C10	112.4 (8)
C7—N1—C8	119.3 (7)	C8—C9—H9A	109.1
C7—N1—Zn1	118.1 (5)	C10—C9—H9A	109.1
C8—N1—Zn1	122.5 (6)	C8—C9—H9B	109.1
C11—N2—C10	115.7 (7)	C10—C9—H9B	109.1
C11—N2—H2A	108.4	H9A—C9—H9B	107.9
C10—N2—H2A	108.4	C9—C10—N2	112.7 (7)
C11—N2—H2B	108.4	C9—C10—H10A	109.1
C10—N2—H2B	108.4	N2—C10—H10A	109.1
H2A—N2—H2B	107.4	C9—C10—H10B	109.1
C6—C1—C2	121.3 (8)	N2—C10—H10B	109.1
C6—C1—C7	114.0 (8)	H10A—C10—H10B	107.8
C2—C1—C7	124.6 (7)	N2—C11—H11A	109.5
O1—C2—C3	119.4 (7)	N2—C11—H11B	109.5
O1—C2—C1	123.7 (7)	H11A—C11—H11B	109.5
C3—C2—C1	116.8 (7)	N2—C11—H11C	109.5
C4—C3—C2	121.9 (9)	H11A—C11—H11C	109.5
C4—C3—O2	124.8 (8)	H11B—C11—H11C	109.5
C2—C3—O2	113.1 (7)	O2—C12—C13	108.8 (8)
C3—C4—C5	120.5 (9)	O2—C12—H12A	109.9
C3—C4—H4	119.8	C13—C12—H12A	109.9
C5—C4—H4	119.8	O2—C12—H12B	109.9
C6—C5—C4	120.1 (9)	C13—C12—H12B	109.9
C6—C5—H5	119.9	H12A—C12—H12B	108.3
C4—C5—H5	119.9	C12—C13—H13A	109.5
C5—C6—C1	119.2 (9)	C12—C13—H13B	109.5
C5—C6—H6	120.4	H13A—C13—H13B	109.5
C1—C6—H6	120.4	C12—C13—H13C	109.5
N1—C7—C1	129.0 (8)	H13A—C13—H13C	109.5
N1—C7—H7	115.5	H13B—C13—H13C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1ⁱ	0.90	1.84	2.697 (8)	158
N2—H2B···O2ⁱ	0.90	2.40	3.005 (8)	124

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

Experimental details

Crystal data
Chemical formula	[ZnBr₂(C₁₃H₂₀N₂O₂)]
M_r	461.50
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	17.884 (3), 14.374 (2), 14.992 (2)
β (°)	114.482 (3)
V (Å³)	3507.4 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.96
Crystal size (mm)	0.23 × 0.21 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.341, 0.368
No. of measured, independent and observed [I > 2σ(I)] reflections	14138, 3787, 1974
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.222, 1.00
No. of reflections	3787
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.12, −0.90

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	1.958 (5)	Zn1—Br1	2.3429 (16)
Zn1—N1	2.014 (6)	Zn1—Br2	2.4046 (18)

O1—Zn1—N1	95.3 (2)	O1—Zn1—Br2	113.02 (17)
O1—Zn1—Br1	115.26 (16)	N1—Zn1—Br2	113.09 (19)
N1—Zn1—Br1	113.83 (19)	Br1—Zn1—Br2	106.38 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1ⁱ	0.90	1.84	2.697 (8)	158
N2—H2B···O2ⁱ	0.90	2.40	3.005 (8)	124

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

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages m1092-m1093

doi:10.1107/S1600536808023672

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­bromido{(E)-2-eth­­oxy-6-[3-(methyl­ammonio)propyl­iminometh­yl]phenol­ato}zinc(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Dibromido{(E)-2-ethoxy-6-[3-(methylammonio)propyliminomethyl]phenolato}zinc(II)