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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m870.
Published online 2009 July 4. doi:  10.1107/S1600536809025215
PMCID: PMC2977511

Chlorido{4-chloro-2-[(2-morpholinoeth­yl)imino­meth­yl]phenolato-κ3 N,N′,O}copper(II)

Abstract

The CuII atom in the title compound, [Cu(C13H16ClN2O2)Cl], exists in a distorted square-planar coordination environment as the deprotonated Schiff base chelates to the CuII atom through three atom sites. In the crystal structure, adjacent mol­ecules are linked by a Cu(...)Cl [3.011 (1) Å] bridge, generating a linear chain running along the b axis of the ortho­rhom­bic unit cell.

Related literature

A similar deprotonated Schiff base is bidentate in bis­{5-meth­oxy-2-[(2-morpholinoeth­yl)imino­meth­yl]phenolato}nickel; see: Mohd Lair et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m870-scheme1.jpg

Experimental

Crystal data

  • [Cu(C13H16ClN2O2)Cl]
  • M r = 366.72
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m870-efi1.jpg
  • a = 23.0936 (6) Å
  • b = 8.4890 (2) Å
  • c = 14.0582 (3) Å
  • V = 2756.0 (1) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.97 mm−1
  • T = 140 K
  • 0.40 × 0.10 × 0.02 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.506, T max = 0.962
  • 17248 measured reflections
  • 3156 independent reflections
  • 2416 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.113
  • S = 1.09
  • 3156 reflections
  • 181 parameters
  • H-atom parameters constrained
  • Δρmax = 0.76 e Å−3
  • Δρmin = −0.84 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025215/xu2547sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025215/xu2547Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

The Schiff base was synthesized by condensing N-2-(aminoethyl)morpholine (0.80 g, 6.1 mmol) and 5-chlorosalicylaldehyde (0.96 g, 6.1 mmol) in ethanol; the reactants were heated for 2 hours. Copper(II) chloride (1.00 g, 6.1 mmol) was added and the heating continued for another 5 hour. The solvent was removed and the product recrystallized from methanol.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.99 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2 times Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the CuCl(C13H16ClN2O2) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[Cu(C13H16ClN2O2)Cl]F(000) = 1496
Mr = 366.72Dx = 1.768 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 4043 reflections
a = 23.0936 (6) Åθ = 2.6–28.1°
b = 8.4890 (2) ŵ = 1.97 mm1
c = 14.0582 (3) ÅT = 140 K
V = 2756.0 (1) Å3Plate, green
Z = 80.40 × 0.10 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer3156 independent reflections
Radiation source: fine-focus sealed tube2416 reflections with I > 2σ(I)
graphiteRint = 0.050
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −29→30
Tmin = 0.506, Tmax = 0.962k = −10→10
17248 measured reflectionsl = −18→18

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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0476P)2 + 6.7938P] where P = (Fo2 + 2Fc2)/3
3156 reflections(Δ/σ)max = 0.001
181 parametersΔρmax = 0.76 e Å3
0 restraintsΔρmin = −0.84 e Å3

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

xyzUiso*/Ueq
Cu10.229938 (18)0.65838 (5)0.49762 (3)0.01385 (13)
Cl10.24525 (4)0.85643 (10)0.39295 (6)0.0181 (2)
Cl20.43295 (4)0.32750 (12)0.83746 (7)0.0253 (2)
O10.30890 (10)0.6693 (3)0.53670 (17)0.0159 (5)
O20.03792 (12)0.7569 (3)0.36877 (18)0.0225 (6)
N10.20874 (13)0.5357 (3)0.60938 (19)0.0141 (6)
N20.14182 (13)0.6347 (3)0.46204 (19)0.0131 (6)
C10.33436 (15)0.5909 (4)0.6049 (2)0.0131 (7)
C20.39494 (16)0.6087 (4)0.6170 (2)0.0158 (7)
H20.41560.67690.57560.019*
C30.42459 (16)0.5294 (4)0.6873 (2)0.0157 (7)
H30.46520.54380.69420.019*
C40.39495 (16)0.4279 (4)0.7485 (2)0.0169 (7)
C50.33647 (16)0.4082 (4)0.7404 (2)0.0158 (7)
H50.31680.33960.78290.019*
C60.30502 (15)0.4889 (4)0.6696 (2)0.0139 (7)
C70.24355 (16)0.4685 (4)0.6681 (2)0.0149 (7)
H70.22710.39980.71410.018*
C80.14665 (15)0.5035 (4)0.6176 (2)0.0147 (7)
H8A0.12720.58910.65310.018*
H8B0.14010.40300.65170.018*
C90.12305 (15)0.4933 (4)0.5171 (2)0.0147 (7)
H9A0.13760.39660.48590.018*
H9B0.08020.48820.51890.018*
C100.11098 (16)0.7815 (4)0.4921 (2)0.0168 (7)
H10A0.12930.87320.46070.020*
H10B0.11550.79490.56170.020*
C110.04724 (17)0.7799 (5)0.4681 (3)0.0209 (8)
H11A0.02800.69430.50400.025*
H11B0.02960.88100.48790.025*
C120.06457 (16)0.6146 (5)0.3373 (3)0.0202 (8)
H12A0.05850.60290.26790.024*
H12B0.04590.52390.36930.024*
C130.12914 (16)0.6129 (5)0.3585 (2)0.0173 (7)
H13A0.14570.51140.33710.021*
H13B0.14820.69810.32200.021*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0132 (2)0.0170 (2)0.0113 (2)−0.00069 (18)−0.00083 (15)0.00270 (17)
Cl10.0202 (4)0.0186 (4)0.0154 (4)−0.0010 (4)−0.0009 (3)0.0058 (3)
Cl20.0222 (5)0.0295 (5)0.0243 (5)−0.0005 (4)−0.0077 (4)0.0126 (4)
O10.0146 (13)0.0158 (13)0.0174 (11)0.0000 (10)−0.0020 (10)0.0069 (10)
O20.0209 (14)0.0274 (15)0.0193 (13)0.0077 (12)−0.0033 (11)0.0008 (11)
N10.0152 (15)0.0145 (15)0.0126 (13)−0.0010 (12)−0.0018 (11)−0.0015 (11)
N20.0163 (15)0.0126 (14)0.0103 (12)0.0011 (12)−0.0014 (11)−0.0013 (11)
C10.0171 (18)0.0117 (17)0.0106 (15)0.0007 (14)−0.0021 (13)−0.0006 (12)
C20.0173 (19)0.0149 (17)0.0151 (16)−0.0030 (15)0.0029 (13)−0.0001 (13)
C30.0154 (18)0.0144 (18)0.0173 (16)−0.0016 (14)−0.0018 (13)−0.0031 (13)
C40.0221 (19)0.0159 (18)0.0126 (15)0.0024 (15)−0.0035 (14)0.0028 (13)
C50.0225 (19)0.0127 (18)0.0121 (15)0.0002 (15)0.0005 (13)0.0006 (13)
C60.0191 (18)0.0119 (16)0.0106 (15)0.0005 (14)0.0001 (13)−0.0007 (12)
C70.0205 (19)0.0142 (17)0.0100 (14)0.0009 (14)0.0029 (13)−0.0002 (13)
C80.0140 (17)0.0166 (17)0.0133 (15)−0.0007 (14)−0.0002 (13)0.0032 (13)
C90.0146 (17)0.0161 (17)0.0135 (16)0.0003 (14)−0.0030 (12)0.0022 (13)
C100.0194 (18)0.0146 (17)0.0164 (16)0.0035 (15)0.0008 (14)−0.0009 (14)
C110.022 (2)0.0218 (19)0.0191 (17)0.0042 (17)0.0028 (15)−0.0031 (15)
C120.020 (2)0.0238 (19)0.0171 (17)0.0009 (16)−0.0031 (14)−0.0020 (15)
C130.0191 (19)0.0198 (18)0.0130 (15)0.0019 (15)−0.0011 (13)−0.0012 (14)

Geometric parameters (Å, °)

Cu1—O11.907 (2)C4—C51.366 (5)
Cu1—N11.947 (3)C5—C61.410 (5)
Cu1—N22.105 (3)C5—H50.9500
Cu1—Cl12.2620 (9)C6—C71.430 (5)
Cu1—Cl1i3.0107 (10)C7—H70.9500
Cl2—C41.750 (3)C8—C91.516 (4)
O1—C11.307 (4)C8—H8A0.9900
O2—C111.427 (4)C8—H8B0.9900
O2—C121.426 (5)C9—H9A0.9900
N1—C71.285 (4)C9—H9B0.9900
N1—C81.464 (4)C10—C111.510 (5)
N2—C91.492 (4)C10—H10A0.9900
N2—C131.496 (4)C10—H10B0.9900
N2—C101.497 (4)C11—H11A0.9900
C1—C21.417 (5)C11—H11B0.9900
C1—C61.427 (5)C12—C131.521 (5)
C2—C31.378 (5)C12—H12A0.9900
C2—H20.9500C12—H12B0.9900
C3—C41.396 (5)C13—H13A0.9900
C3—H30.9500C13—H13B0.9900
O1—Cu1—N191.95 (11)N1—C7—C6125.2 (3)
O1—Cu1—N2176.00 (11)N1—C7—H7117.4
N1—Cu1—N284.12 (12)C6—C7—H7117.4
O1—Cu1—Cl190.10 (7)N1—C8—C9106.8 (3)
N1—Cu1—Cl1164.06 (9)N1—C8—H8A110.4
N2—Cu1—Cl193.88 (8)C9—C8—H8A110.4
O1—Cu1—Cl1i90.02 (8)N1—C8—H8B110.4
N1—Cu1—Cl1i89.25 (9)C9—C8—H8B110.4
N2—Cu1—Cl1i89.22 (8)H8A—C8—H8B108.6
Cl1—Cu1—Cl1i106.56 (3)N2—C9—C8109.5 (3)
C1—O1—Cu1128.1 (2)N2—C9—H9A109.8
C11—O2—C12110.8 (3)C8—C9—H9A109.8
C7—N1—C8118.6 (3)N2—C9—H9B109.8
C7—N1—Cu1126.7 (3)C8—C9—H9B109.8
C8—N1—Cu1114.2 (2)H9A—C9—H9B108.2
C9—N2—C13110.4 (3)N2—C10—C11113.1 (3)
C9—N2—C10112.6 (3)N2—C10—H10A109.0
C13—N2—C10106.5 (3)C11—C10—H10A109.0
C9—N2—Cu1103.6 (2)N2—C10—H10B109.0
C13—N2—Cu1115.6 (2)C11—C10—H10B109.0
C10—N2—Cu1108.2 (2)H10A—C10—H10B107.8
O1—C1—C2118.5 (3)O2—C11—C10111.5 (3)
O1—C1—C6124.3 (3)O2—C11—H11A109.3
C2—C1—C6117.2 (3)C10—C11—H11A109.3
C3—C2—C1121.6 (3)O2—C11—H11B109.3
C3—C2—H2119.2C10—C11—H11B109.3
C1—C2—H2119.2H11A—C11—H11B108.0
C2—C3—C4120.0 (3)O2—C12—C13111.7 (3)
C2—C3—H3120.0O2—C12—H12A109.3
C4—C3—H3120.0C13—C12—H12A109.3
C5—C4—C3120.6 (3)O2—C12—H12B109.3
C5—C4—Cl2119.7 (3)C13—C12—H12B109.3
C3—C4—Cl2119.7 (3)H12A—C12—H12B107.9
C4—C5—C6120.5 (3)N2—C13—C12112.4 (3)
C4—C5—H5119.7N2—C13—H13A109.1
C6—C5—H5119.7C12—C13—H13A109.1
C5—C6—C7117.6 (3)N2—C13—H13B109.1
C5—C6—C1120.0 (3)C12—C13—H13B109.1
C7—C6—C1122.4 (3)H13A—C13—H13B107.8
N1—Cu1—O1—C111.0 (3)Cl2—C4—C5—C6179.6 (3)
Cl1—Cu1—O1—C1175.2 (3)C4—C5—C6—C7−177.2 (3)
Cl1i—Cu1—O1—C1−78.2 (3)C4—C5—C6—C10.6 (5)
O1—Cu1—N1—C7−12.6 (3)O1—C1—C6—C5179.4 (3)
N2—Cu1—N1—C7166.6 (3)C2—C1—C6—C5−1.3 (5)
Cl1—Cu1—N1—C7−109.8 (4)O1—C1—C6—C7−2.9 (5)
Cl1i—Cu1—N1—C777.4 (3)C2—C1—C6—C7176.3 (3)
O1—Cu1—N1—C8175.5 (2)C8—N1—C7—C6−179.5 (3)
N2—Cu1—N1—C8−5.2 (2)Cu1—N1—C7—C69.0 (5)
Cl1—Cu1—N1—C878.3 (4)C5—C6—C7—N1178.7 (3)
Cl1i—Cu1—N1—C8−94.5 (2)C1—C6—C7—N11.0 (5)
N1—Cu1—N2—C9−21.8 (2)C7—N1—C8—C9−141.6 (3)
Cl1—Cu1—N2—C9174.03 (19)Cu1—N1—C8—C930.9 (3)
Cl1i—Cu1—N2—C967.48 (19)C13—N2—C9—C8169.0 (3)
N1—Cu1—N2—C13−142.8 (3)C10—N2—C9—C8−72.1 (3)
Cl1—Cu1—N2—C1353.1 (2)Cu1—N2—C9—C844.6 (3)
Cl1i—Cu1—N2—C13−53.4 (2)N1—C8—C9—N2−50.7 (4)
N1—Cu1—N2—C1097.9 (2)C9—N2—C10—C11−67.4 (4)
Cl1—Cu1—N2—C10−66.2 (2)C13—N2—C10—C1153.8 (4)
Cl1i—Cu1—N2—C10−172.8 (2)Cu1—N2—C10—C11178.7 (2)
Cu1—O1—C1—C2175.2 (2)C12—O2—C11—C1057.0 (4)
Cu1—O1—C1—C6−5.6 (5)N2—C10—C11—O2−57.2 (4)
O1—C1—C2—C3−179.9 (3)C11—O2—C12—C13−57.2 (4)
C6—C1—C2—C30.8 (5)C9—N2—C13—C1269.1 (4)
C1—C2—C3—C40.4 (5)C10—N2—C13—C12−53.5 (4)
C2—C3—C4—C5−1.2 (5)Cu1—N2—C13—C12−173.8 (2)
C2—C3—C4—Cl2179.9 (3)O2—C12—C13—N257.4 (4)
C3—C4—C5—C60.7 (5)

Symmetry codes: (i) −x+1/2, y−1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2547).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, m733. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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