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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): m555.
Published online 2009 April 22. doi:  10.1107/S1600536809011684
PMCID: PMC2977602

Dichlorido{2-[(4-iodo­phen­yl)imino­meth­yl]pyridine-κ2 N,N′}copper(II)

Abstract

The CuII atom in the title complex, [CuCl2(C12H9IN2)], has a square-planar coordination being N,N′-chelated by the Schiff base ligand, and by two Cl atoms. The geometry is distorted towards square pyramidal owing to a long Cu(...)Cl inter­action of 2.941 (1) Å. This results in the formation of a zigzag chain structure propagating in the c-axis direction.

Related literature

For background to the synthesis and structure of metal complexes of diimines, see: Yamada (1999 [triangle]). For the structure of the zinc chloride complex of the same ligand, see: Dehghanpour et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m555-scheme1.jpg

Experimental

Crystal data

  • [CuCl2(C12H9IN2)]
  • M r = 442.55
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m555-efi1.jpg
  • a = 12.2721 (5) Å
  • b = 15.2159 (5) Å
  • c = 7.4709 (2) Å
  • β = 94.8913 (10)°
  • V = 1389.97 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 4.16 mm−1
  • T = 295 K
  • 0.31 × 0.25 × 0.17 mm

Data collection

  • Rigaku RAXIS-RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.359, T max = 0.538 (expected range = 0.329–0.493)
  • 21713 measured reflections
  • 3166 independent reflections
  • 2650 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.079
  • S = 1.05
  • 3166 reflections
  • 163 parameters
  • H-atom parameters constrained
  • Δρmax = 0.88 e Å−3
  • Δρmin = −0.51 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, 9R. DOI: 10.1107/S1600536809011684/su2104sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011684/su2104Isup2.hkl

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

Acknowledgments

We thank the Islamic Azad University Research Council and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The structure of the title complex is illustrated in Fig. 1, and the geometrical parameters are available in the archived CIF. The complex was prepared by the reaction of copper chloride with the Schiff base ligand 2-[(4-iodophenyl)iminomethyl]pyridine (Yamada, 1999). The ligand is slightly twisted with the benzene ring and pyridine ring being inclined to one another by 26.07813)°.

A long Cu···Cl2i [symmetry operation (i) = x, 1.5-y, 0.5+z] interaction of 2.941 (1) Å, leads the formation of a zigzag chain propagating in the c direction (Fig. 2). This situation is different to that observed in the ZnCl2 complex of the same ligand, which is mononuclear (Dehghanpour et al., 2007).

Experimental

To a solution of 2-[(4-iodophenyl)iminomethyl]pyridine (30.8 mg, 0.1 mmol) in 20 ml acetonitrile was added copper(II) chloride (13.4 mg, 0.1 mmol). The mixture was heated to dissolve the reactants and then the solution was filtered and the volume reduced under vacuum to ca. 5 ml. Diffusion of diethyl ether vapor into the solution gave green crystals of the title complex. The crystals were collected and washed with diethylether-dichloromethane (9:1 v/v). Yield 75%. CHN elemental analysis: Calc. for C12H9Cl2CuIN2: C 32.57, H 2.05, N 6.33%; found: C 32.54, H 2.07, N 6.35%.

Refinement

The H-atoms were placed in calculated positions [C—H 0.93 Å] and treated as riding atoms [Uiso(H) = 1.2Ueq(C)].

Figures

Fig. 1.
A view of the structure of the title complex, with displacement ellipsoids drawn at the 50% probability level [H atoms are represented as spheres of arbitrary radius].
Fig. 2.
A view of the Cu···Cl2i bridged zigzag bridged chain structure of the title compound [Symmetry operations (i) = x, 1.5-y, -0.5+z]

Crystal data

[CuCl2(C12H9IN2)]F(000) = 844
Mr = 442.55Dx = 2.115 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 13838 reflections
a = 12.2721 (5) Åθ = 3.1–27.5°
b = 15.2159 (5) ŵ = 4.16 mm1
c = 7.4709 (2) ÅT = 295 K
β = 94.8913 (10)°Block, green
V = 1389.97 (8) Å30.31 × 0.25 × 0.17 mm
Z = 4

Data collection

Rigaku RAXIS-RAPID diffractometer3166 independent reflections
Radiation source: fine-focus sealed tube2650 reflections with I > 2σ(I)
graphiteRint = 0.037
Detector resolution: 10.000 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = −15→15
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −19→19
Tmin = 0.359, Tmax = 0.538l = −9→9
21713 measured reflections

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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0447P)2 + 0.6865P] where P = (Fo2 + 2Fc2)/3
3166 reflections(Δ/σ)max = 0.001
163 parametersΔρmax = 0.88 e Å3
0 restraintsΔρmin = −0.51 e Å3

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

xyzUiso*/Ueq
I1−0.001646 (16)0.649922 (16)0.55181 (3)0.05798 (10)
Cu10.60873 (3)0.72391 (2)0.87653 (5)0.03844 (11)
Cl10.72032 (6)0.82416 (5)1.01818 (12)0.05137 (19)
Cl20.51519 (6)0.82558 (5)0.71178 (11)0.04616 (18)
N10.70612 (18)0.62040 (15)0.9438 (3)0.0375 (5)
N20.50252 (17)0.62295 (15)0.7935 (3)0.0334 (4)
C10.8056 (2)0.6212 (2)1.0289 (4)0.0469 (7)
H10.83440.67381.07520.056*
C20.8676 (2)0.5448 (2)1.0503 (5)0.0520 (8)
H20.93680.54631.11140.062*
C30.8259 (3)0.4672 (2)0.9809 (5)0.0489 (7)
H30.86770.41620.98950.059*
C40.7210 (3)0.4657 (2)0.8980 (4)0.0443 (6)
H40.69020.41350.85300.053*
C50.6629 (2)0.54354 (18)0.8832 (4)0.0365 (6)
C60.5499 (2)0.54841 (18)0.8064 (4)0.0378 (6)
H60.51280.49770.76720.045*
C70.3893 (2)0.62851 (18)0.7297 (4)0.0350 (5)
C80.3398 (2)0.5679 (2)0.6095 (4)0.0446 (6)
H80.38140.52330.56430.054*
C90.2287 (2)0.5736 (2)0.5565 (4)0.0479 (7)
H90.19570.53230.47750.057*
C100.1677 (2)0.64099 (19)0.6219 (4)0.0417 (6)
C110.2166 (2)0.70219 (19)0.7420 (4)0.0422 (6)
H110.17530.74750.78520.051*
C120.3266 (2)0.69542 (18)0.7964 (4)0.0385 (6)
H120.35910.73570.87810.046*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
I10.02714 (12)0.06908 (18)0.07514 (18)0.00149 (8)−0.01061 (10)0.00131 (11)
Cu10.02850 (18)0.03088 (18)0.0536 (2)0.00103 (12)−0.00989 (14)−0.00045 (14)
Cl10.0377 (4)0.0440 (4)0.0702 (5)−0.0064 (3)−0.0082 (3)−0.0106 (4)
Cl20.0382 (4)0.0366 (3)0.0624 (4)0.0042 (3)−0.0032 (3)0.0115 (3)
N10.0270 (11)0.0373 (11)0.0472 (12)0.0010 (9)−0.0036 (9)0.0017 (11)
N20.0265 (11)0.0321 (10)0.0404 (11)0.0000 (8)−0.0033 (8)0.0008 (9)
C10.0306 (14)0.0500 (16)0.0578 (17)0.0032 (12)−0.0087 (12)−0.0016 (15)
C20.0279 (14)0.0624 (19)0.0640 (19)0.0063 (13)−0.0055 (13)0.0086 (16)
C30.0358 (16)0.0470 (16)0.0640 (18)0.0124 (12)0.0054 (13)0.0129 (15)
C40.0390 (15)0.0367 (14)0.0570 (17)0.0040 (11)0.0022 (13)0.0056 (13)
C50.0287 (13)0.0353 (13)0.0449 (14)0.0019 (10)−0.0002 (10)0.0041 (12)
C60.0315 (13)0.0325 (13)0.0484 (15)−0.0023 (10)−0.0027 (11)0.0010 (12)
C70.0264 (12)0.0349 (12)0.0429 (13)0.0000 (10)−0.0022 (10)0.0020 (12)
C80.0304 (14)0.0513 (17)0.0513 (16)0.0015 (12)−0.0014 (11)−0.0108 (14)
C90.0331 (15)0.0581 (18)0.0507 (16)−0.0033 (13)−0.0069 (12)−0.0096 (15)
C100.0244 (13)0.0492 (16)0.0503 (16)−0.0011 (11)−0.0046 (11)0.0049 (13)
C110.0320 (14)0.0387 (14)0.0556 (16)0.0054 (11)0.0017 (11)0.0012 (13)
C120.0326 (14)0.0360 (13)0.0457 (14)−0.0010 (11)−0.0036 (11)−0.0015 (12)

Geometric parameters (Å, °)

I1—C102.104 (3)C4—C51.383 (4)
Cu1—N12.015 (2)C4—H40.9300
Cu1—N22.075 (2)C5—C61.457 (4)
Cu1—Cl12.253 (1)C6—H60.9300
Cu1—Cl22.233 (1)C7—C81.390 (4)
N1—C11.328 (4)C7—C121.393 (4)
N1—C51.346 (4)C8—C91.389 (4)
N2—C61.274 (4)C8—H80.9300
N2—C71.433 (3)C9—C101.384 (4)
C1—C21.391 (4)C9—H90.9300
C1—H10.9300C10—C111.393 (4)
C2—C31.371 (5)C11—C121.380 (4)
C2—H20.9300C11—H110.9300
C3—C41.380 (4)C12—H120.9300
C3—H30.9300
N1—Cu1—N280.79 (9)N1—C5—C4122.1 (3)
N1—Cu1—Cl2160.96 (7)N1—C5—C6115.0 (2)
N1—Cu1—Cl195.07 (7)C4—C5—C6122.8 (3)
N2—Cu1—Cl1169.40 (7)N2—C6—C5119.2 (2)
N2—Cu1—Cl293.89 (6)N2—C6—H6120.4
Cl1—Cu2—Cl193.05 (3)C5—C6—H6120.4
C1—N1—C5119.3 (2)C8—C7—C12119.5 (2)
C1—N1—Cu1127.9 (2)C8—C7—N2122.2 (2)
C5—N1—Cu1112.76 (17)C12—C7—N2118.3 (2)
C6—N2—C7120.1 (2)C7—C8—C9120.5 (3)
C6—N2—Cu1111.44 (18)C7—C8—H8119.8
C7—N2—Cu1128.50 (17)C9—C8—H8119.8
N1—C1—C2121.2 (3)C10—C9—C8119.5 (3)
N1—C1—H1119.4C10—C9—H9120.3
C2—C1—H1119.4C8—C9—H9120.3
C3—C2—C1119.6 (3)C9—C10—C11120.4 (3)
C3—C2—H2120.2C9—C10—I1120.9 (2)
C1—C2—H2120.2C11—C10—I1118.7 (2)
C2—C3—C4119.2 (3)C12—C11—C10119.8 (3)
C2—C3—H3120.4C12—C11—H11120.1
C4—C3—H3120.4C10—C11—H11120.1
C3—C4—C5118.5 (3)C11—C12—C7120.3 (3)
C3—C4—H4120.8C11—C12—H12119.8
C5—C4—H4120.8C7—C12—H12119.8
N2—Cu1—N1—C1−175.5 (3)C3—C4—C5—N11.4 (5)
Cl2—Cu1—N1—C1109.5 (3)C3—C4—C5—C6−176.8 (3)
Cl1—Cu1—N1—C1−5.4 (3)C7—N2—C6—C5−175.7 (2)
N2—Cu1—N1—C58.14 (19)Cu1—N2—C6—C53.6 (3)
Cl2—Cu1—N1—C5−66.8 (3)N1—C5—C6—N23.3 (4)
Cl1—Cu1—N1—C5178.30 (18)C4—C5—C6—N2−178.3 (3)
N1—Cu1—N2—C6−6.3 (2)C6—N2—C7—C8−29.4 (4)
Cl2—Cu1—N2—C6155.25 (19)Cu1—N2—C7—C8151.3 (2)
Cl1—Cu1—N2—C6−74.0 (4)C6—N2—C7—C12148.2 (3)
N1—Cu1—N2—C7172.9 (2)Cu1—N2—C7—C12−31.0 (3)
Cl2—Cu1—N2—C7−25.5 (2)C12—C7—C8—C9−0.2 (4)
Cl1—Cu1—N2—C7105.3 (4)N2—C7—C8—C9177.4 (3)
C5—N1—C1—C22.6 (5)C7—C8—C9—C101.1 (5)
Cu1—N1—C1—C2−173.5 (2)C8—C9—C10—C11−0.8 (5)
N1—C1—C2—C30.6 (5)C8—C9—C10—I1−178.1 (2)
C1—C2—C3—C4−2.9 (5)C9—C10—C11—C12−0.2 (5)
C2—C3—C4—C51.9 (5)I1—C10—C11—C12177.1 (2)
C1—N1—C5—C4−3.7 (4)C10—C11—C12—C71.0 (4)
Cu1—N1—C5—C4173.0 (2)C8—C7—C12—C11−0.8 (4)
C1—N1—C5—C6174.7 (3)N2—C7—C12—C11−178.6 (3)
Cu1—N1—C5—C6−8.6 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2104).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Dehghanpour, S., Mahmoudi, A., Khalaj, M., Salmanpour, S. & Adib, M. (2007). Acta Cryst. E63, m2841.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yamada, S. (1999). Coord. Chem. Rev.190, 537–555.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography