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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): m469.
Published online 2010 March 31. doi:  10.1107/S160053681001127X
PMCID: PMC2983844

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

Abstract

The ZnII 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 [triangle]). For similar zinc(II) complexes with Schiff bases, see: Ali et al. (2008 [triangle]); Wang (2007 [triangle]); Zhang et al. (2008 [triangle]); Zhu et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m469-scheme1.jpg

Experimental

Crystal data

  • [ZnCl2(C13H20N2O2)]
  • M r = 372.58
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m469-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.086
  • S = 1.01
  • 3557 reflections
  • 184 parameters
  • H-atom parameters constrained
  • Δρmax = 0.46 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681001127X/bx2273sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge Qiqihar University for a research grant.

supplementary crystallographic information

Comment

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 ZnII 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.

Experimental

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.

Refinement

H atoms were placed in idealized positions and constrained to ride on their parent atoms with C–H distances in the range 0.93-0.97 Å, N–H distances of 0.90 Å, and with Uiso(H) set at 1.2Ueq(C,N) and 1.5Ueq(methyl C).

Figures

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.

Crystal data

[ZnCl2(C13H20N2O2)]F(000) = 768
Mr = 372.58Dx = 1.504 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.2915 (9) ÅCell parameters from 1935 reflections
b = 11.8990 (18) Åθ = 2.5–24.5°
c = 22.115 (4) ŵ = 1.82 mm1
β = 96.518 (4)°T = 298 K
V = 1644.9 (4) Å3Block, colourless
Z = 40.18 × 0.18 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer3557 independent reflections
Radiation source: fine-focus sealed tube2515 reflections with I > 2σ(I)
graphiteRint = 0.042
ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→8
Tmin = 0.735, Tmax = 0.735k = −13→15
9437 measured reflectionsl = −27→28

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0339P)2 + 0.3384P] where P = (Fo2 + 2Fc2)/3
3557 reflections(Δ/σ)max = 0.001
184 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = −0.31 e Å3

Special details

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)

xyzUiso*/Ueq
Zn10.75702 (6)0.83340 (3)0.763592 (16)0.03646 (12)
Cl10.56343 (14)0.81826 (7)0.67166 (4)0.0519 (2)
Cl21.00002 (12)0.97048 (6)0.77248 (4)0.0497 (2)
N10.8725 (4)0.68364 (18)0.79167 (11)0.0336 (6)
N20.9034 (4)0.58914 (18)0.66336 (10)0.0329 (6)
H2A0.77880.59590.67940.039*
H2B0.94120.51620.66580.039*
O10.5732 (3)0.85623 (15)0.82740 (9)0.0399 (5)
O20.0900 (4)0.7411 (2)0.95938 (11)0.0652 (7)
C10.6016 (5)0.6635 (2)0.86232 (13)0.0360 (7)
C20.5081 (5)0.7727 (2)0.85973 (13)0.0336 (7)
C30.3364 (5)0.7916 (2)0.89406 (14)0.0397 (7)
H30.27350.86250.89310.048*
C40.2582 (5)0.7086 (3)0.92900 (14)0.0449 (8)
C50.3475 (6)0.6021 (3)0.93171 (16)0.0524 (9)
H50.29560.54600.95540.063*
C60.5158 (5)0.5815 (3)0.89822 (15)0.0483 (8)
H60.57520.50990.89950.058*
C70.7806 (5)0.6282 (2)0.83109 (13)0.0367 (7)
H70.83530.55710.84080.044*
C81.0626 (5)0.6333 (3)0.76875 (14)0.0417 (8)
H8A1.06220.55280.77580.050*
H8B1.19070.66400.79130.050*
C91.0685 (5)0.6552 (2)0.70159 (14)0.0374 (7)
H9A1.04540.73460.69350.045*
H9B1.20890.63580.69060.045*
C100.8660 (6)0.6211 (3)0.59723 (15)0.0513 (9)
H100.81150.69830.59520.062*
C110.6940 (6)0.5472 (3)0.56592 (17)0.0732 (12)
H11A0.74280.47070.56690.110*
H11B0.66130.57090.52440.110*
H11C0.56790.55260.58640.110*
C121.0658 (7)0.6201 (4)0.56802 (18)0.0780 (13)
H12A1.12820.54650.57150.117*
H12B1.16430.67380.58780.117*
H12C1.03460.63940.52580.117*
C130.0014 (7)0.6613 (3)0.99717 (18)0.0725 (12)
H13A−0.04950.59740.97320.109*
H13B−0.11550.69491.01500.109*
H13C0.10920.63761.02880.109*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0419 (2)0.02734 (18)0.0413 (2)0.00185 (15)0.00994 (15)−0.00074 (15)
Cl10.0564 (5)0.0489 (5)0.0486 (5)0.0057 (4)−0.0021 (4)−0.0049 (4)
Cl20.0413 (5)0.0393 (4)0.0687 (6)−0.0057 (4)0.0072 (4)0.0064 (4)
N10.0342 (14)0.0289 (13)0.0369 (14)0.0010 (10)0.0005 (11)−0.0047 (10)
N20.0353 (14)0.0291 (12)0.0351 (14)0.0002 (10)0.0076 (11)−0.0013 (10)
O10.0491 (13)0.0260 (10)0.0477 (13)0.0021 (9)0.0186 (11)0.0011 (9)
O20.0748 (18)0.0618 (15)0.0661 (17)−0.0106 (13)0.0389 (15)−0.0050 (13)
C10.0391 (17)0.0321 (15)0.0365 (17)−0.0011 (13)0.0028 (13)−0.0009 (13)
C20.0367 (17)0.0316 (16)0.0320 (17)−0.0050 (13)0.0018 (13)−0.0046 (13)
C30.0457 (19)0.0347 (16)0.0399 (18)−0.0030 (14)0.0095 (15)−0.0069 (14)
C40.047 (2)0.051 (2)0.0370 (18)−0.0116 (16)0.0082 (15)−0.0074 (15)
C50.061 (2)0.048 (2)0.050 (2)−0.0107 (17)0.0151 (18)0.0073 (16)
C60.055 (2)0.0361 (17)0.054 (2)−0.0002 (15)0.0057 (18)0.0081 (15)
C70.0444 (18)0.0255 (14)0.0384 (18)0.0035 (13)−0.0035 (15)−0.0021 (13)
C80.0338 (17)0.0439 (18)0.046 (2)0.0068 (14)0.0002 (14)−0.0072 (14)
C90.0297 (15)0.0320 (16)0.051 (2)−0.0015 (13)0.0076 (14)−0.0029 (14)
C100.069 (2)0.0459 (19)0.039 (2)0.0039 (18)0.0056 (18)0.0044 (15)
C110.085 (3)0.084 (3)0.046 (2)−0.011 (2)−0.014 (2)−0.005 (2)
C120.085 (3)0.095 (3)0.058 (3)0.002 (3)0.025 (2)0.011 (2)
C130.082 (3)0.080 (3)0.062 (3)−0.020 (2)0.035 (2)0.000 (2)

Geometric parameters (Å, °)

Zn1—O11.9425 (19)C5—H50.9300
Zn1—N11.997 (2)C6—H60.9300
Zn1—Cl22.2290 (9)C7—H70.9300
Zn1—Cl12.2554 (10)C8—C91.513 (4)
N1—C71.282 (3)C8—H8A0.9700
N1—C81.478 (3)C8—H8B0.9700
N2—C91.487 (4)C9—H9A0.9700
N2—C101.504 (4)C9—H9B0.9700
N2—H2A0.9000C10—C121.477 (5)
N2—H2B0.9000C10—C111.502 (5)
O1—C21.317 (3)C10—H100.9800
O2—C41.372 (4)C11—H11A0.9600
O2—C131.420 (4)C11—H11B0.9600
C1—C61.404 (4)C11—H11C0.9600
C1—C21.425 (4)C12—H12A0.9600
C1—C71.448 (4)C12—H12B0.9600
C2—C31.408 (4)C12—H12C0.9600
C3—C41.379 (4)C13—H13A0.9600
C3—H30.9300C13—H13B0.9600
C4—C51.385 (4)C13—H13C0.9600
C5—C61.381 (4)
O1—Zn1—N197.16 (9)C1—C7—H7116.2
O1—Zn1—Cl2107.02 (6)N1—C8—C9112.2 (2)
N1—Zn1—Cl2113.82 (7)N1—C8—H8A109.2
O1—Zn1—Cl1111.15 (7)C9—C8—H8A109.2
N1—Zn1—Cl1110.44 (7)N1—C8—H8B109.2
Cl2—Zn1—Cl1115.64 (3)C9—C8—H8B109.2
C7—N1—C8118.0 (2)H8A—C8—H8B107.9
C7—N1—Zn1119.60 (19)N2—C9—C8111.9 (2)
C8—N1—Zn1122.37 (19)N2—C9—H9A109.2
C9—N2—C10116.2 (2)C8—C9—H9A109.2
C9—N2—H2A108.2N2—C9—H9B109.2
C10—N2—H2A108.2C8—C9—H9B109.2
C9—N2—H2B108.2H9A—C9—H9B107.9
C10—N2—H2B108.2C12—C10—C11113.4 (3)
H2A—N2—H2B107.4C12—C10—N2112.1 (3)
C2—O1—Zn1122.43 (17)C11—C10—N2109.0 (3)
C4—O2—C13118.4 (3)C12—C10—H10107.3
C6—C1—C2118.2 (3)C11—C10—H10107.3
C6—C1—C7116.0 (3)N2—C10—H10107.3
C2—C1—C7125.8 (3)C10—C11—H11A109.5
O1—C2—C3118.5 (2)C10—C11—H11B109.5
O1—C2—C1123.9 (2)H11A—C11—H11B109.5
C3—C2—C1117.6 (3)C10—C11—H11C109.5
C4—C3—C2122.1 (3)H11A—C11—H11C109.5
C4—C3—H3118.9H11B—C11—H11C109.5
C2—C3—H3118.9C10—C12—H12A109.5
O2—C4—C3114.6 (3)C10—C12—H12B109.5
O2—C4—C5124.6 (3)H12A—C12—H12B109.5
C3—C4—C5120.8 (3)C10—C12—H12C109.5
C6—C5—C4118.1 (3)H12A—C12—H12C109.5
C6—C5—H5121.0H12B—C12—H12C109.5
C4—C5—H5121.0O2—C13—H13A109.5
C5—C6—C1123.2 (3)O2—C13—H13B109.5
C5—C6—H6118.4H13A—C13—H13B109.5
C1—C6—H6118.4O2—C13—H13C109.5
N1—C7—C1127.6 (3)H13A—C13—H13C109.5
N1—C7—H7116.2H13B—C13—H13C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···Cl2i0.902.623.357 (2)140
N2—H2B···O1i0.901.912.782 (3)162
N2—H2A···Cl10.902.973.483 (2)118

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2273).

References

  • Ali, H. M., Mohamed Mustafa, M. I., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, m718–m719. [PMC free article] [PubMed]
  • Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Han, Z.-Q. (2008). Acta Cryst. E64, m592. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, S.-X. (2007). Acta Cryst. E63, m706–m707.
  • Zhang, D.-F., Zhou, M.-H. & Yuan, C.-J. (2008). Acta Cryst. E64, m825–m826. [PMC free article] [PubMed]
  • Zhu, X.-W., Yang, X.-Z., Zhang, C.-X., Li, G.-S. & Yin, Z.-G. (2009). Acta Cryst. E65, m1332–m1333. [PMC free article] [PubMed]

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