Dichlorido{2-[(2-isopropyl­ammonio­ethyl)imino­meth­yl]-5-methoxy­phenolato}zinc(II)

Han, Z.-Q.; Wang, Y.; Han, S.

doi:10.1107/S160053681001127X

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page m469

doi:10.1107/S160053681001127X

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Dichlorido{2-[(2-isopropylammonioethyl)iminomethyl]-5-methoxyphenolato}zinc(II)

Zhen-Quan Han,^a ^* Yuan Wang ^b and Shuang Han ^c

^aApplied Technical College, Qiqihar University, Qiqihar 161006, People's Republic of China, ^bQiqihar Environmental Monitoring Central Station, Qiqihar 161005, People's Republic of China, and ^cCollege of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar 161006, People's Republic of China
^*Correspondence e-mail: zhenquan_han@126.com

(Received 19 March 2010; accepted 24 March 2010; online 31 March 2010)

The Zn^II atom in the title compound, [ZnCl₂(C₁₃H₂₀N₂O₂)], is four-coordinated by the imine N and phenolate O atoms of the zwitterionic Schiff base ligand, and by two choride ions in a distorted tetrahedral coordination. In the crystal structure, molecules are linked through intermolecular N—H⋯O and N—H⋯Cl hydrogen bonds along [010].

Related literature

For a nickel(II) complex with the 3-ethoxysalicylaldehyde ligand, see: Han (2008 ). For similar zinc(II) complexes with Schiff bases, see: Ali et al. (2008 ); Wang (2007 ); Zhang et al. (2008 ); Zhu et al. (2009 ).

Experimental

Crystal data

[ZnCl₂(C₁₃H₂₀N₂O₂)]
M_r = 372.58
Monoclinic, P 2₁ /n
a = 6.2915 (9) Å
b = 11.8990 (18) Å
c = 22.115 (4) Å
β = 96.518 (4)°
V = 1644.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.82 mm⁻¹
T = 298 K
0.18 × 0.18 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.735, T_max = 0.735
9437 measured reflections
3557 independent reflections
2515 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.086
S = 1.01
3557 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—O1	1.9425 (19)
Zn1—N1	1.997 (2)
Zn1—Cl2	2.2290 (9)
Zn1—Cl1	2.2554 (10)

O1—Zn1—N1	97.16 (9)
O1—Zn1—Cl2	107.02 (6)
N1—Zn1—Cl2	113.82 (7)
O1—Zn1—Cl1	111.15 (7)
N1—Zn1—Cl1	110.44 (7)
Cl2—Zn1—Cl1	115.64 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl2ⁱ	0.90	2.62	3.357 (2)	140
N2—H2B⋯O1ⁱ	0.90	1.91	2.782 (3)	162
N2—H2A⋯Cl1	0.90	2.97	3.483 (2)	118
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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: 10.1107/S160053681001127X/bx2273sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681001127X/bx2273Isup2.hkl

checkCIF report

Comment top

Recently, we have reported a nickel(II) complex with the ligand 3-ethoxysalicylaldehyde (Han, 2008). We report here a new zinc(II) complex derived from the Schiff base ligand 2-[(2-isopropylammonioethylimino)methyl]-5-methoxyphenol, which was formed by the condensation reaction of 4-methoxysalicylaldehyde with N-isopropylethane-1,2-diamine in a methanol solution.The Zn^II atom is four-coordinated by the imine N and phenolate O atoms of the Schiff base ligand, and by two choride ions in a distorted tetrahedral coordination. In the crystal structure, molecules are linked through intermolecular N—H··· O and N—H ···O and hydrogen bonds along [010], (Fig. 2). The geometric parameters are comparable to those in similar zinc(II) complexes with Schiff bases (Wang, 2007; Ali et al., 2008; Zhang et al., 2008; Zhu et al., 2009) as representative examples.

Related literature top

For a nickel(II) complex with the 3-ethoxysalicylaldehyde ligand, see: Han (2008). For similar zinc(II) complexes with Schiff bases, see: Ali et al. (2008); Wang (2007); Zhang et al. (2008); Zhu et al. (2009).

Experimental top

All the chemicals were of AR grade. 4-Methoxysalicylaldehyde (30.4 mg, 0.2 mmol) and N-isopropylethane-1,2-diamine (20.4 mg, 0.2 mmol) were stirred in a methanol solution for 2 h at reflux. Then the zinc(II) chloride (27.5 mg, 0.2 mmol) was added to the mixture. The mixture was further stirred at reflux for 1 h. The mixture was cooled to room temperature and filtered. After keeping the filtrate in air for a week, yielding colorless block crystals suitable for X-ray analysis.

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 structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Molecular packing of the title complex.

Dichlorido{2-[(2-isopropylammonioethyl)iminomethyl]-5-methoxyphenolato}zinc(II) top

Crystal data top

[ZnCl₂(C₁₃H₂₀N₂O₂)]	F(000) = 768
M_r = 372.58	D_x = 1.504 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.2915 (9) Å	Cell parameters from 1935 reflections
b = 11.8990 (18) Å	θ = 2.5–24.5°
c = 22.115 (4) Å	µ = 1.82 mm⁻¹
β = 96.518 (4)°	T = 298 K
V = 1644.9 (4) Å³	Block, colourless
Z = 4	0.18 × 0.18 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3557 independent reflections
Radiation source: fine-focus sealed tube	2515 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
T_min = 0.735, T_max = 0.735	k = −13→15
9437 measured reflections	l = −27→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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0339P)² + 0.3384P] where P = (F_o² + 2F_c²)/3
3557 reflections	(Δ/σ)_max = 0.001
184 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[ZnCl₂(C₁₃H₂₀N₂O₂)]	V = 1644.9 (4) Å³
M_r = 372.58	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.2915 (9) Å	µ = 1.82 mm⁻¹
b = 11.8990 (18) Å	T = 298 K
c = 22.115 (4) Å	0.18 × 0.18 × 0.18 mm
β = 96.518 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3557 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2515 reflections with I > 2σ(I)
T_min = 0.735, T_max = 0.735	R_int = 0.042
9437 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.01	Δρ_max = 0.46 e Å⁻³
3557 reflections	Δρ_min = −0.31 e Å⁻³
184 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	0.75702 (6)	0.83340 (3)	0.763592 (16)	0.03646 (12)
Cl1	0.56343 (14)	0.81826 (7)	0.67166 (4)	0.0519 (2)
Cl2	1.00002 (12)	0.97048 (6)	0.77248 (4)	0.0497 (2)
N1	0.8725 (4)	0.68364 (18)	0.79167 (11)	0.0336 (6)
N2	0.9034 (4)	0.58914 (18)	0.66336 (10)	0.0329 (6)
H2A	0.7788	0.5959	0.6794	0.039*
H2B	0.9412	0.5162	0.6658	0.039*
O1	0.5732 (3)	0.85623 (15)	0.82740 (9)	0.0399 (5)
O2	0.0900 (4)	0.7411 (2)	0.95938 (11)	0.0652 (7)
C1	0.6016 (5)	0.6635 (2)	0.86232 (13)	0.0360 (7)
C2	0.5081 (5)	0.7727 (2)	0.85973 (13)	0.0336 (7)
C3	0.3364 (5)	0.7916 (2)	0.89406 (14)	0.0397 (7)
H3	0.2735	0.8625	0.8931	0.048*
C4	0.2582 (5)	0.7086 (3)	0.92900 (14)	0.0449 (8)
C5	0.3475 (6)	0.6021 (3)	0.93171 (16)	0.0524 (9)
H5	0.2956	0.5460	0.9554	0.063*
C6	0.5158 (5)	0.5815 (3)	0.89822 (15)	0.0483 (8)
H6	0.5752	0.5099	0.8995	0.058*
C7	0.7806 (5)	0.6282 (2)	0.83109 (13)	0.0367 (7)
H7	0.8353	0.5571	0.8408	0.044*
C8	1.0626 (5)	0.6333 (3)	0.76875 (14)	0.0417 (8)
H8A	1.0622	0.5528	0.7758	0.050*
H8B	1.1907	0.6640	0.7913	0.050*
C9	1.0685 (5)	0.6552 (2)	0.70159 (14)	0.0374 (7)
H9A	1.0454	0.7346	0.6935	0.045*
H9B	1.2089	0.6358	0.6906	0.045*
C10	0.8660 (6)	0.6211 (3)	0.59723 (15)	0.0513 (9)
H10	0.8115	0.6983	0.5952	0.062*
C11	0.6940 (6)	0.5472 (3)	0.56592 (17)	0.0732 (12)
H11A	0.7428	0.4707	0.5669	0.110*
H11B	0.6613	0.5709	0.5244	0.110*
H11C	0.5679	0.5526	0.5864	0.110*
C12	1.0658 (7)	0.6201 (4)	0.56802 (18)	0.0780 (13)
H12A	1.1282	0.5465	0.5715	0.117*
H12B	1.1643	0.6738	0.5878	0.117*
H12C	1.0346	0.6394	0.5258	0.117*
C13	0.0014 (7)	0.6613 (3)	0.99717 (18)	0.0725 (12)
H13A	−0.0495	0.5974	0.9732	0.109*
H13B	−0.1155	0.6949	1.0150	0.109*
H13C	0.1092	0.6376	1.0288	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0419 (2)	0.02734 (18)	0.0413 (2)	0.00185 (15)	0.00994 (15)	−0.00074 (15)
Cl1	0.0564 (5)	0.0489 (5)	0.0486 (5)	0.0057 (4)	−0.0021 (4)	−0.0049 (4)
Cl2	0.0413 (5)	0.0393 (4)	0.0687 (6)	−0.0057 (4)	0.0072 (4)	0.0064 (4)
N1	0.0342 (14)	0.0289 (13)	0.0369 (14)	0.0010 (10)	0.0005 (11)	−0.0047 (10)
N2	0.0353 (14)	0.0291 (12)	0.0351 (14)	0.0002 (10)	0.0076 (11)	−0.0013 (10)
O1	0.0491 (13)	0.0260 (10)	0.0477 (13)	0.0021 (9)	0.0186 (11)	0.0011 (9)
O2	0.0748 (18)	0.0618 (15)	0.0661 (17)	−0.0106 (13)	0.0389 (15)	−0.0050 (13)
C1	0.0391 (17)	0.0321 (15)	0.0365 (17)	−0.0011 (13)	0.0028 (13)	−0.0009 (13)
C2	0.0367 (17)	0.0316 (16)	0.0320 (17)	−0.0050 (13)	0.0018 (13)	−0.0046 (13)
C3	0.0457 (19)	0.0347 (16)	0.0399 (18)	−0.0030 (14)	0.0095 (15)	−0.0069 (14)
C4	0.047 (2)	0.051 (2)	0.0370 (18)	−0.0116 (16)	0.0082 (15)	−0.0074 (15)
C5	0.061 (2)	0.048 (2)	0.050 (2)	−0.0107 (17)	0.0151 (18)	0.0073 (16)
C6	0.055 (2)	0.0361 (17)	0.054 (2)	−0.0002 (15)	0.0057 (18)	0.0081 (15)
C7	0.0444 (18)	0.0255 (14)	0.0384 (18)	0.0035 (13)	−0.0035 (15)	−0.0021 (13)
C8	0.0338 (17)	0.0439 (18)	0.046 (2)	0.0068 (14)	0.0002 (14)	−0.0072 (14)
C9	0.0297 (15)	0.0320 (16)	0.051 (2)	−0.0015 (13)	0.0076 (14)	−0.0029 (14)
C10	0.069 (2)	0.0459 (19)	0.039 (2)	0.0039 (18)	0.0056 (18)	0.0044 (15)
C11	0.085 (3)	0.084 (3)	0.046 (2)	−0.011 (2)	−0.014 (2)	−0.005 (2)
C12	0.085 (3)	0.095 (3)	0.058 (3)	0.002 (3)	0.025 (2)	0.011 (2)
C13	0.082 (3)	0.080 (3)	0.062 (3)	−0.020 (2)	0.035 (2)	0.000 (2)

Geometric parameters (Å, º) top

Zn1—O1	1.9425 (19)	C5—H5	0.9300
Zn1—N1	1.997 (2)	C6—H6	0.9300
Zn1—Cl2	2.2290 (9)	C7—H7	0.9300
Zn1—Cl1	2.2554 (10)	C8—C9	1.513 (4)
N1—C7	1.282 (3)	C8—H8A	0.9700
N1—C8	1.478 (3)	C8—H8B	0.9700
N2—C9	1.487 (4)	C9—H9A	0.9700
N2—C10	1.504 (4)	C9—H9B	0.9700
N2—H2A	0.9000	C10—C12	1.477 (5)
N2—H2B	0.9000	C10—C11	1.502 (5)
O1—C2	1.317 (3)	C10—H10	0.9800
O2—C4	1.372 (4)	C11—H11A	0.9600
O2—C13	1.420 (4)	C11—H11B	0.9600
C1—C6	1.404 (4)	C11—H11C	0.9600
C1—C2	1.425 (4)	C12—H12A	0.9600
C1—C7	1.448 (4)	C12—H12B	0.9600
C2—C3	1.408 (4)	C12—H12C	0.9600
C3—C4	1.379 (4)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.385 (4)	C13—H13C	0.9600
C5—C6	1.381 (4)

O1—Zn1—N1	97.16 (9)	C1—C7—H7	116.2
O1—Zn1—Cl2	107.02 (6)	N1—C8—C9	112.2 (2)
N1—Zn1—Cl2	113.82 (7)	N1—C8—H8A	109.2
O1—Zn1—Cl1	111.15 (7)	C9—C8—H8A	109.2
N1—Zn1—Cl1	110.44 (7)	N1—C8—H8B	109.2
Cl2—Zn1—Cl1	115.64 (3)	C9—C8—H8B	109.2
C7—N1—C8	118.0 (2)	H8A—C8—H8B	107.9
C7—N1—Zn1	119.60 (19)	N2—C9—C8	111.9 (2)
C8—N1—Zn1	122.37 (19)	N2—C9—H9A	109.2
C9—N2—C10	116.2 (2)	C8—C9—H9A	109.2
C9—N2—H2A	108.2	N2—C9—H9B	109.2
C10—N2—H2A	108.2	C8—C9—H9B	109.2
C9—N2—H2B	108.2	H9A—C9—H9B	107.9
C10—N2—H2B	108.2	C12—C10—C11	113.4 (3)
H2A—N2—H2B	107.4	C12—C10—N2	112.1 (3)
C2—O1—Zn1	122.43 (17)	C11—C10—N2	109.0 (3)
C4—O2—C13	118.4 (3)	C12—C10—H10	107.3
C6—C1—C2	118.2 (3)	C11—C10—H10	107.3
C6—C1—C7	116.0 (3)	N2—C10—H10	107.3
C2—C1—C7	125.8 (3)	C10—C11—H11A	109.5
O1—C2—C3	118.5 (2)	C10—C11—H11B	109.5
O1—C2—C1	123.9 (2)	H11A—C11—H11B	109.5
C3—C2—C1	117.6 (3)	C10—C11—H11C	109.5
C4—C3—C2	122.1 (3)	H11A—C11—H11C	109.5
C4—C3—H3	118.9	H11B—C11—H11C	109.5
C2—C3—H3	118.9	C10—C12—H12A	109.5
O2—C4—C3	114.6 (3)	C10—C12—H12B	109.5
O2—C4—C5	124.6 (3)	H12A—C12—H12B	109.5
C3—C4—C5	120.8 (3)	C10—C12—H12C	109.5
C6—C5—C4	118.1 (3)	H12A—C12—H12C	109.5
C6—C5—H5	121.0	H12B—C12—H12C	109.5
C4—C5—H5	121.0	O2—C13—H13A	109.5
C5—C6—C1	123.2 (3)	O2—C13—H13B	109.5
C5—C6—H6	118.4	H13A—C13—H13B	109.5
C1—C6—H6	118.4	O2—C13—H13C	109.5
N1—C7—C1	127.6 (3)	H13A—C13—H13C	109.5
N1—C7—H7	116.2	H13B—C13—H13C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl2ⁱ	0.90	2.62	3.357 (2)	140
N2—H2B···O1ⁱ	0.90	1.91	2.782 (3)	162
N2—H2A···Cl1	0.90	2.97	3.483 (2)	118

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

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₁₃H₂₀N₂O₂)]
M_r	372.58
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	6.2915 (9), 11.8990 (18), 22.115 (4)
β (°)	96.518 (4)
V (Å³)	1644.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.82
Crystal size (mm)	0.18 × 0.18 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.735, 0.735
No. of measured, independent and observed [I > 2σ(I)] reflections	9437, 3557, 2515
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.086, 1.01
No. of reflections	3557
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −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	1.9425 (19)	Zn1—Cl2	2.2290 (9)
Zn1—N1	1.997 (2)	Zn1—Cl1	2.2554 (10)

O1—Zn1—N1	97.16 (9)	O1—Zn1—Cl1	111.15 (7)
O1—Zn1—Cl2	107.02 (6)	N1—Zn1—Cl1	110.44 (7)
N1—Zn1—Cl2	113.82 (7)	Cl2—Zn1—Cl1	115.64 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl2ⁱ	0.90	2.62	3.357 (2)	139.7
N2—H2B···O1ⁱ	0.90	1.91	2.782 (3)	161.8
N2—H2A···Cl1	0.90	2.97	3.483 (2)	118.0

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

Acknowledgements

The authors acknowledge Qiqihar University for a research grant.

References

Ali, H. M., Mohamed Mustafa, M. I., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, m718–m719. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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Volume 66| Part 4| April 2010| Page m469

doi:10.1107/S160053681001127X

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

Di­chlorido{2-[(2-iso­propyl­ammonio­ethyl)imino­meth­yl]-5-meth­oxy­phenolato}zinc(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Dichlorido{2-[(2-isopropylammonioethyl)iminomethyl]-5-methoxyphenolato}zinc(II)