Dichlorido{2-[2-(dimethyl­ammonio)ethyl­imino­meth­yl]-6-methoxy­phenolato}zinc(II)

Datta, A.; Chuang, N.-T.; Huang, J.-H.; Lee, H.M.

doi:10.1107/S1600536809028220

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m964

doi:10.1107/S1600536809028220

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Dichlorido{2-[2-(dimethylammonio)ethyliminomethyl]-6-methoxyphenolato}zinc(II)

Amitabha Datta,^a Nien-Tsu Chuang,^a Jui-Hsien Huang ^a and Hon Man Lee ^a ^*

^aNational Changhua University of Education, Department of Chemistry, Changhua, Taiwan 50058
^*Correspondence e-mail: leehm@cc.ncue.edu.tw

(Received 3 July 2009; accepted 17 July 2009; online 22 July 2009)

The structure of the title complex, [ZnCl₂(C₁₂H₁₈N₂O₂)], contains a zwitterionic Schiff base ligand. The complex adopts a distorted tetrahedral coordination geometry around the metal centre with the Schiff base ligand coordinated in a bidentate fashion via the imine N and phenolate O atoms. In the crystal, intermolecular N—H⋯O and C—H⋯Cl hydrogen bonds link the molecules into chains parallel to the c-glide planes.

Related literature

For bidentate Schiff base–Zn(II) complexes, see: Qiu (2006 ); Wang & Qiu (2006 ); Ye & You (2008 ); You (2005a ,b ); Zhu (2008 ).

Experimental

Crystal data

[ZnCl₂(C₁₂H₁₈N₂O₂)]
M_r = 358.55
Monoclinic, P 2₁ /c
a = 8.5621 (6) Å
b = 16.9642 (12) Å
c = 13.1106 (7) Å
β = 127.732 (3)°
V = 1506.08 (17) Å³
Z = 4
Mo Kα radiation
μ = 1.98 mm⁻¹
T = 298 K
0.32 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.552, T_max = 0.649
8355 measured reflections
2960 independent reflections
2439 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.075
S = 1.01
2960 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.91	1.97	2.842 (2)	161
N1—H1⋯O2ⁱ	0.91	2.38	2.985 (2)	124
C5—H5⋯Cl2ⁱ	0.93	2.80	3.617 (2)	148
Symmetry code: (i) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028220/bh2237sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028220/bh2237Isup2.hkl

checkCIF report

Comment top

The Schiff base 2-((2-(dimethylamino)ethylimino)methyl)-6-methoxyphenol reacts with zinc(II) chloride in methanol to form the title complex. It adopts tetrahedron coordination geometry with the Schiff base ligand coordinated via the imine N and the phenolate O atoms. A formal proton transfer of the phenolic hydrogen to the amine N atom occurred leading to the formation of the neutral O/N-bidentate ligand bearing a pendant ammonium group.

Bidentate Schiff base Zn(II) complexes similar to the title complex were reported in the literature (Qiu, 2006; Wang & Qiu, 2006; Ye & You, 2008; You, 2005a, b; Zhu, 2008).

Classical intermolecular H-bonds of the type N—H···O and non-classical H-bonds of the type C—H···Cl exist (Table 1). These H-bonds link the complex into one-dimensional hydrogen bonded chains.

Related literature top

For bidentate Schiff base–Zn(II) complexes, see: Qiu (2006); Wang & Qiu (2006); Ye & You (2008); You (2005a,b); Zhu (2008).

Experimental top

To an aqueous solution (20 ml) of zinc(II) chloride (0.136 g, 1.00 mmol), a methanolic solution of the Schiff base 2-((2-(dimethylamino)ethylimino)methyl)-6-methoxyphenol (1.00 mmol) was added. The resulting mixture was kept at room temperature yielding brown block-like crystals suitable for X-ray diffraction after few days. Crystals were isolated by filtration and were dried in the air.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title complex, showing 50% displacement ellipsoids for non-H atoms. The H atoms are depicted by circles of arbitrary radius.
	Fig. 2. A packing diagram of the title compound showing the intermolecular hydrogen bonds (dashed lines).

Dichlorido{2-[2-(dimethylammonio)ethyliminomethyl]-6-methoxyphenolato}zinc(II) top

Crystal data top

[ZnCl₂(C₁₂H₁₈N₂O₂)]	F(000) = 736
M_r = 358.55	D_x = 1.581 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4320 reflections
a = 8.5621 (6) Å	θ = 2.4–26.0°
b = 16.9642 (12) Å	µ = 1.98 mm⁻¹
c = 13.1106 (7) Å	T = 298 K
β = 127.732 (3)°	Block, brown
V = 1506.08 (17) Å³	0.32 × 0.25 × 0.22 mm
Z = 4

Data collection top

Bruker SMART APEXII diffractometer	2960 independent reflections
Radiation source: fine-focus sealed tube	2439 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→9
T_min = 0.552, T_max = 0.649	k = −20→20
8355 measured reflections	l = −10→16

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0461P)²] where P = (F_o² + 2F_c²)/3
2960 reflections	(Δ/σ)_max = 0.001
175 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³
0 constraints

Crystal data top

[ZnCl₂(C₁₂H₁₈N₂O₂)]	V = 1506.08 (17) Å³
M_r = 358.55	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.5621 (6) Å	µ = 1.98 mm⁻¹
b = 16.9642 (12) Å	T = 298 K
c = 13.1106 (7) Å	0.32 × 0.25 × 0.22 mm
β = 127.732 (3)°

Data collection top

Bruker SMART APEXII diffractometer	2960 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2439 reflections with I > 2σ(I)
T_min = 0.552, T_max = 0.649	R_int = 0.030
8355 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.01	Δρ_max = 0.35 e Å⁻³
2960 reflections	Δρ_min = −0.34 e Å⁻³
175 parameters

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

	x	y	z	U_iso*/U_eq
Zn1	0.68123 (3)	0.747503 (13)	0.52685 (2)	0.02988 (10)
Cl1	0.60094 (9)	0.72171 (4)	0.65804 (6)	0.04492 (16)
Cl2	0.86631 (8)	0.65127 (4)	0.53283 (6)	0.04647 (17)
O1	0.7870 (2)	0.85437 (8)	0.55417 (13)	0.0336 (3)
O2	0.9469 (2)	0.99419 (9)	0.62283 (15)	0.0432 (4)
N1	0.1190 (3)	0.63462 (11)	0.31873 (17)	0.0357 (4)
H1	0.0110	0.6259	0.2358	0.043*
N2	0.4369 (2)	0.76199 (10)	0.34509 (17)	0.0285 (4)
C1	0.1242 (4)	0.57202 (15)	0.4010 (2)	0.0512 (6)
H1A	0.0034	0.5732	0.3910	0.077*
H1B	0.2336	0.5813	0.4897	0.077*
H1C	0.1388	0.5214	0.3751	0.077*
C2	0.0953 (3)	0.71360 (15)	0.3580 (2)	0.0442 (6)
H2A	0.0800	0.7530	0.2999	0.066*
H2B	0.2101	0.7253	0.4441	0.066*
H2C	−0.0194	0.7133	0.3552	0.066*
C3	0.2983 (3)	0.62794 (13)	0.3237 (2)	0.0364 (5)
H3A	0.2912	0.5786	0.2837	0.044*
H3B	0.4144	0.6258	0.4134	0.044*
C4	0.3242 (3)	0.69479 (13)	0.2580 (2)	0.0354 (5)
H4A	0.3921	0.6749	0.2253	0.043*
H4B	0.1951	0.7132	0.1850	0.043*
C5	0.3886 (3)	0.83097 (13)	0.2944 (2)	0.0324 (5)
H5	0.2768	0.8338	0.2087	0.039*
C6	0.4879 (3)	0.90494 (12)	0.35490 (19)	0.0302 (5)
C7	0.3821 (3)	0.97261 (14)	0.2809 (2)	0.0393 (5)
H7	0.2582	0.9666	0.2018	0.047*
C8	0.4579 (4)	1.04639 (14)	0.3232 (2)	0.0432 (6)
H8	0.3841	1.0903	0.2750	0.052*
C9	0.6463 (3)	1.05555 (13)	0.4387 (2)	0.0397 (5)
H9	0.6988	1.1059	0.4674	0.048*
C10	0.7563 (3)	0.99069 (12)	0.5115 (2)	0.0321 (5)
C11	0.6771 (3)	0.91289 (12)	0.47493 (19)	0.0280 (4)
C12	1.0452 (4)	1.06907 (14)	0.6573 (3)	0.0537 (7)
H12A	0.9871	1.1044	0.6828	0.081*
H12B	1.0314	1.0907	0.5845	0.081*
H12C	1.1827	1.0622	0.7276	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02911 (15)	0.02351 (15)	0.03349 (16)	−0.00104 (9)	0.01735 (12)	0.00050 (9)
Cl1	0.0429 (3)	0.0566 (4)	0.0423 (3)	0.0001 (3)	0.0297 (3)	0.0034 (3)
Cl2	0.0428 (3)	0.0418 (3)	0.0553 (4)	0.0101 (3)	0.0303 (3)	−0.0005 (3)
O1	0.0304 (7)	0.0224 (8)	0.0340 (8)	−0.0004 (6)	0.0126 (6)	0.0016 (6)
O2	0.0423 (9)	0.0256 (8)	0.0426 (9)	−0.0090 (7)	0.0163 (8)	−0.0024 (7)
N1	0.0308 (9)	0.0373 (11)	0.0342 (10)	−0.0060 (8)	0.0175 (8)	−0.0036 (8)
N2	0.0267 (8)	0.0282 (10)	0.0314 (9)	−0.0047 (7)	0.0183 (8)	−0.0039 (7)
C1	0.0598 (16)	0.0482 (16)	0.0506 (15)	−0.0093 (12)	0.0363 (14)	0.0020 (12)
C2	0.0353 (12)	0.0465 (15)	0.0497 (14)	0.0028 (11)	0.0254 (11)	−0.0053 (11)
C3	0.0323 (11)	0.0282 (12)	0.0454 (13)	−0.0019 (9)	0.0220 (10)	−0.0063 (9)
C4	0.0360 (11)	0.0366 (13)	0.0353 (12)	−0.0084 (9)	0.0227 (10)	−0.0113 (9)
C5	0.0286 (10)	0.0379 (13)	0.0312 (11)	0.0001 (9)	0.0186 (9)	0.0028 (9)
C6	0.0325 (10)	0.0273 (11)	0.0343 (11)	0.0011 (8)	0.0222 (9)	0.0028 (8)
C7	0.0364 (12)	0.0376 (13)	0.0380 (12)	0.0038 (10)	0.0197 (10)	0.0080 (10)
C8	0.0462 (14)	0.0292 (13)	0.0490 (14)	0.0094 (10)	0.0264 (12)	0.0145 (10)
C9	0.0508 (14)	0.0250 (12)	0.0480 (14)	−0.0013 (10)	0.0326 (12)	0.0041 (10)
C10	0.0364 (12)	0.0264 (11)	0.0334 (11)	−0.0013 (9)	0.0214 (10)	0.0004 (9)
C11	0.0317 (10)	0.0260 (11)	0.0315 (11)	0.0007 (8)	0.0219 (9)	0.0027 (8)
C12	0.0561 (16)	0.0275 (14)	0.0609 (17)	−0.0159 (11)	0.0272 (14)	−0.0082 (11)

Geometric parameters (Å, º) top

Zn1—O1	1.9590 (14)	C3—C4	1.521 (3)
Zn1—N2	2.0034 (18)	C3—H3A	0.9700
Zn1—Cl2	2.2429 (6)	C3—H3B	0.9700
Zn1—Cl1	2.2516 (6)	C4—H4A	0.9700
O1—C11	1.324 (2)	C4—H4B	0.9700
O2—C10	1.372 (3)	C5—C6	1.450 (3)
O2—C12	1.435 (3)	C5—H5	0.9300
N1—C2	1.493 (3)	C6—C11	1.414 (3)
N1—C1	1.495 (3)	C6—C7	1.415 (3)
N1—C3	1.500 (3)	C7—C8	1.362 (3)
N1—H1	0.9100	C7—H7	0.9300
N2—C5	1.283 (3)	C8—C9	1.389 (3)
N2—C4	1.479 (3)	C8—H8	0.9300
C1—H1A	0.9600	C9—C10	1.381 (3)
C1—H1B	0.9600	C9—H9	0.9300
C1—H1C	0.9600	C10—C11	1.426 (3)
C2—H2A	0.9600	C12—H12A	0.9600
C2—H2B	0.9600	C12—H12B	0.9600
C2—H2C	0.9600	C12—H12C	0.9600

O1—Zn1—N2	97.67 (6)	H3A—C3—H3B	107.5
O1—Zn1—Cl2	115.44 (5)	N2—C4—C3	112.94 (18)
N2—Zn1—Cl2	109.39 (5)	N2—C4—H4A	109.0
O1—Zn1—Cl1	111.30 (5)	C3—C4—H4A	109.0
N2—Zn1—Cl1	110.35 (5)	N2—C4—H4B	109.0
Cl2—Zn1—Cl1	111.80 (3)	C3—C4—H4B	109.0
C11—O1—Zn1	121.55 (13)	H4A—C4—H4B	107.8
C10—O2—C12	117.37 (18)	N2—C5—C6	127.7 (2)
C2—N1—C1	109.82 (19)	N2—C5—H5	116.2
C2—N1—C3	113.83 (16)	C6—C5—H5	116.2
C1—N1—C3	109.71 (18)	C11—C6—C7	120.1 (2)
C2—N1—H1	107.8	C11—C6—C5	125.47 (19)
C1—N1—H1	107.8	C7—C6—C5	114.34 (19)
C3—N1—H1	107.8	C8—C7—C6	121.4 (2)
C5—N2—C4	116.87 (19)	C8—C7—H7	119.3
C5—N2—Zn1	119.94 (14)	C6—C7—H7	119.3
C4—N2—Zn1	122.48 (14)	C7—C8—C9	119.5 (2)
N1—C1—H1A	109.5	C7—C8—H8	120.2
N1—C1—H1B	109.5	C9—C8—H8	120.2
H1A—C1—H1B	109.5	C10—C9—C8	120.7 (2)
N1—C1—H1C	109.5	C10—C9—H9	119.7
H1A—C1—H1C	109.5	C8—C9—H9	119.7
H1B—C1—H1C	109.5	O2—C10—C9	124.4 (2)
N1—C2—H2A	109.5	O2—C10—C11	114.14 (18)
N1—C2—H2B	109.5	C9—C10—C11	121.5 (2)
H2A—C2—H2B	109.5	O1—C11—C6	125.57 (19)
N1—C2—H2C	109.5	O1—C11—C10	117.83 (18)
H2A—C2—H2C	109.5	C6—C11—C10	116.59 (18)
H2B—C2—H2C	109.5	O2—C12—H12A	109.5
N1—C3—C4	114.78 (18)	O2—C12—H12B	109.5
N1—C3—H3A	108.6	H12A—C12—H12B	109.5
C4—C3—H3A	108.6	O2—C12—H12C	109.5
N1—C3—H3B	108.6	H12A—C12—H12C	109.5
C4—C3—H3B	108.6	H12B—C12—H12C	109.5

N2—Zn1—O1—C11	14.33 (16)	C11—C6—C7—C8	−0.5 (3)
Cl2—Zn1—O1—C11	130.12 (14)	C5—C6—C7—C8	−178.3 (2)
Cl1—Zn1—O1—C11	−101.07 (15)	C6—C7—C8—C9	2.7 (4)
O1—Zn1—N2—C5	−8.41 (17)	C7—C8—C9—C10	−0.6 (4)
Cl2—Zn1—N2—C5	−128.86 (16)	C12—O2—C10—C9	−7.6 (3)
Cl1—Zn1—N2—C5	107.74 (16)	C12—O2—C10—C11	172.5 (2)
O1—Zn1—N2—C4	161.59 (15)	C8—C9—C10—O2	176.4 (2)
Cl2—Zn1—N2—C4	41.14 (16)	C8—C9—C10—C11	−3.7 (3)
Cl1—Zn1—N2—C4	−82.26 (15)	Zn1—O1—C11—C6	−9.9 (3)
C2—N1—C3—C4	−48.9 (2)	Zn1—O1—C11—C10	171.41 (14)
C1—N1—C3—C4	−172.44 (19)	C7—C6—C11—O1	177.8 (2)
C5—N2—C4—C3	−146.55 (19)	C5—C6—C11—O1	−4.7 (3)
Zn1—N2—C4—C3	43.2 (2)	C7—C6—C11—C10	−3.5 (3)
N1—C3—C4—N2	88.5 (2)	C5—C6—C11—C10	174.0 (2)
C4—N2—C5—C6	−173.07 (19)	O2—C10—C11—O1	4.4 (3)
Zn1—N2—C5—C6	−2.5 (3)	C9—C10—C11—O1	−175.5 (2)
N2—C5—C6—C11	12.0 (4)	O2—C10—C11—C6	−174.43 (18)
N2—C5—C6—C7	−170.4 (2)	C9—C10—C11—C6	5.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.91	1.97	2.842 (2)	161
N1—H1···O2ⁱ	0.91	2.38	2.985 (2)	124
C5—H5···Cl2ⁱ	0.93	2.80	3.617 (2)	148

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

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₁₂H₁₈N₂O₂)]
M_r	358.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.5621 (6), 16.9642 (12), 13.1106 (7)
β (°)	127.732 (3)
V (Å³)	1506.08 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.98
Crystal size (mm)	0.32 × 0.25 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.552, 0.649
No. of measured, independent and observed [I > 2σ(I)] reflections	8355, 2960, 2439
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.075, 1.01
No. of reflections	2960
No. of parameters	175
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.34

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.91	1.97	2.842 (2)	161
N1—H1···O2ⁱ	0.91	2.38	2.985 (2)	124
C5—H5···Cl2ⁱ	0.93	2.80	3.617 (2)	148

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

Acknowledgements

We are grateful to the National Science Council of Taiwan for financial support.

References

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Zhu, X.-W. (2008). Acta Cryst. E64, m1456–m1457. Web of Science CrossRef IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m964

doi:10.1107/S1600536809028220

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

Di­chlorido{2-[2-(di­methyl­ammonio)ethyl­imino­meth­yl]-6-meth­oxy­phenolato}zinc(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Dichlorido{2-[2-(dimethylammonio)ethyliminomethyl]-6-methoxyphenolato}zinc(II)