Acta Cryst. (2009). E65, m555 [ doi:10.1107/S1600536809011684 ]
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2N,N'}copper(II)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.
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%.
The H-atoms were placed in calculated positions [C—H 0.93 Å] and treated as riding atoms [Uiso(H) = 1.2Ueq(C)].
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./su2104fig1thm.gif)
| 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]. |
![[Figure 2]](./su2104fig2thm.gif)
| 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] |
| [CuCl2(C12H9IN2)] | F(000) = 844 |
| Mr = 442.55 | Dx = 2.115 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 13838 reflections |
| a = 12.2721 (5) Å | θ = 3.1–27.5° |
| b = 15.2159 (5) Å | µ = 4.16 mm−1 |
| c = 7.4709 (2) Å | T = 295 K |
| β = 94.8913 (10)° | Block, green |
| V = 1389.97 (8) Å3 | 0.31 × 0.25 × 0.17 mm |
| Z = 4 |
| Rigaku RAXIS-RAPID diffractometer | 3166 independent reflections |
| Radiation source: fine-focus sealed tube | 2650 reflections with I > 2σ(I) |
| graphite | Rint = 0.037 |
| Detector resolution: 10.000 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
| ω scans | h = −15→15 |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −19→19 |
| Tmin = 0.359, Tmax = 0.538 | l = −9→9 |
| 21713 measured reflections |
| 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) = 0.079 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0447P)2 + 0.6865P] where P = (Fo2 + 2Fc2)/3 |
| 3166 reflections | (Δ/σ)max = 0.001 |
| 163 parameters | Δρmax = 0.88 e Å−3 |
| 0 restraints | Δρmin = −0.51 e Å−3 |
| [CuCl2(C12H9IN2)] | V = 1389.97 (8) Å3 |
| Mr = 442.55 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 12.2721 (5) Å | µ = 4.16 mm−1 |
| b = 15.2159 (5) Å | T = 295 K |
| c = 7.4709 (2) Å | 0.31 × 0.25 × 0.17 mm |
| β = 94.8913 (10)° |
| Rigaku RAXIS-RAPID diffractometer | 3166 independent reflections |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2650 reflections with I > 2σ(I) |
| Tmin = 0.359, Tmax = 0.538 | Rint = 0.037 |
| 21713 measured reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
| wR(F2) = 0.079 | Δρmax = 0.88 e Å−3 |
| S = 1.05 | Δρmin = −0.51 e Å−3 |
| 3166 reflections | Absolute structure: ? |
| 163 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
| x | y | z | Uiso*/Ueq | ||
| I1 | −0.001646 (16) | 0.649922 (16) | 0.55181 (3) | 0.05798 (10) | |
| Cu1 | 0.60873 (3) | 0.72391 (2) | 0.87653 (5) | 0.03844 (11) | |
| Cl1 | 0.72032 (6) | 0.82416 (5) | 1.01818 (12) | 0.05137 (19) | |
| Cl2 | 0.51519 (6) | 0.82558 (5) | 0.71178 (11) | 0.04616 (18) | |
| N1 | 0.70612 (18) | 0.62040 (15) | 0.9438 (3) | 0.0375 (5) | |
| N2 | 0.50252 (17) | 0.62295 (15) | 0.7935 (3) | 0.0334 (4) | |
| C1 | 0.8056 (2) | 0.6212 (2) | 1.0289 (4) | 0.0469 (7) | |
| H1 | 0.8344 | 0.6738 | 1.0752 | 0.056* | |
| C2 | 0.8676 (2) | 0.5448 (2) | 1.0503 (5) | 0.0520 (8) | |
| H2 | 0.9368 | 0.5463 | 1.1114 | 0.062* | |
| C3 | 0.8259 (3) | 0.4672 (2) | 0.9809 (5) | 0.0489 (7) | |
| H3 | 0.8677 | 0.4162 | 0.9895 | 0.059* | |
| C4 | 0.7210 (3) | 0.4657 (2) | 0.8980 (4) | 0.0443 (6) | |
| H4 | 0.6902 | 0.4135 | 0.8530 | 0.053* | |
| C5 | 0.6629 (2) | 0.54354 (18) | 0.8832 (4) | 0.0365 (6) | |
| C6 | 0.5499 (2) | 0.54841 (18) | 0.8064 (4) | 0.0378 (6) | |
| H6 | 0.5128 | 0.4977 | 0.7672 | 0.045* | |
| C7 | 0.3893 (2) | 0.62851 (18) | 0.7297 (4) | 0.0350 (5) | |
| C8 | 0.3398 (2) | 0.5679 (2) | 0.6095 (4) | 0.0446 (6) | |
| H8 | 0.3814 | 0.5233 | 0.5643 | 0.054* | |
| C9 | 0.2287 (2) | 0.5736 (2) | 0.5565 (4) | 0.0479 (7) | |
| H9 | 0.1957 | 0.5323 | 0.4775 | 0.057* | |
| C10 | 0.1677 (2) | 0.64099 (19) | 0.6219 (4) | 0.0417 (6) | |
| C11 | 0.2166 (2) | 0.70219 (19) | 0.7420 (4) | 0.0422 (6) | |
| H11 | 0.1753 | 0.7475 | 0.7852 | 0.051* | |
| C12 | 0.3266 (2) | 0.69542 (18) | 0.7964 (4) | 0.0385 (6) | |
| H12 | 0.3591 | 0.7357 | 0.8781 | 0.046* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| I1 | 0.02714 (12) | 0.06908 (18) | 0.07514 (18) | 0.00149 (8) | −0.01061 (10) | 0.00131 (11) |
| Cu1 | 0.02850 (18) | 0.03088 (18) | 0.0536 (2) | 0.00103 (12) | −0.00989 (14) | −0.00045 (14) |
| Cl1 | 0.0377 (4) | 0.0440 (4) | 0.0702 (5) | −0.0064 (3) | −0.0082 (3) | −0.0106 (4) |
| Cl2 | 0.0382 (4) | 0.0366 (3) | 0.0624 (4) | 0.0042 (3) | −0.0032 (3) | 0.0115 (3) |
| N1 | 0.0270 (11) | 0.0373 (11) | 0.0472 (12) | 0.0010 (9) | −0.0036 (9) | 0.0017 (11) |
| N2 | 0.0265 (11) | 0.0321 (10) | 0.0404 (11) | 0.0000 (8) | −0.0033 (8) | 0.0008 (9) |
| C1 | 0.0306 (14) | 0.0500 (16) | 0.0578 (17) | 0.0032 (12) | −0.0087 (12) | −0.0016 (15) |
| C2 | 0.0279 (14) | 0.0624 (19) | 0.0640 (19) | 0.0063 (13) | −0.0055 (13) | 0.0086 (16) |
| C3 | 0.0358 (16) | 0.0470 (16) | 0.0640 (18) | 0.0124 (12) | 0.0054 (13) | 0.0129 (15) |
| C4 | 0.0390 (15) | 0.0367 (14) | 0.0570 (17) | 0.0040 (11) | 0.0022 (13) | 0.0056 (13) |
| C5 | 0.0287 (13) | 0.0353 (13) | 0.0449 (14) | 0.0019 (10) | −0.0002 (10) | 0.0041 (12) |
| C6 | 0.0315 (13) | 0.0325 (13) | 0.0484 (15) | −0.0023 (10) | −0.0027 (11) | 0.0010 (12) |
| C7 | 0.0264 (12) | 0.0349 (12) | 0.0429 (13) | 0.0000 (10) | −0.0022 (10) | 0.0020 (12) |
| C8 | 0.0304 (14) | 0.0513 (17) | 0.0513 (16) | 0.0015 (12) | −0.0014 (11) | −0.0108 (14) |
| C9 | 0.0331 (15) | 0.0581 (18) | 0.0507 (16) | −0.0033 (13) | −0.0069 (12) | −0.0096 (15) |
| C10 | 0.0244 (13) | 0.0492 (16) | 0.0503 (16) | −0.0011 (11) | −0.0046 (11) | 0.0049 (13) |
| C11 | 0.0320 (14) | 0.0387 (14) | 0.0556 (16) | 0.0054 (11) | 0.0017 (11) | 0.0012 (13) |
| C12 | 0.0326 (14) | 0.0360 (13) | 0.0457 (14) | −0.0010 (11) | −0.0036 (11) | −0.0015 (12) |
| I1—C10 | 2.104 (3) | C4—C5 | 1.383 (4) |
| Cu1—N1 | 2.015 (2) | C4—H4 | 0.9300 |
| Cu1—N2 | 2.075 (2) | C5—C6 | 1.457 (4) |
| Cu1—Cl1 | 2.253 (1) | C6—H6 | 0.9300 |
| Cu1—Cl2 | 2.233 (1) | C7—C8 | 1.390 (4) |
| N1—C1 | 1.328 (4) | C7—C12 | 1.393 (4) |
| N1—C5 | 1.346 (4) | C8—C9 | 1.389 (4) |
| N2—C6 | 1.274 (4) | C8—H8 | 0.9300 |
| N2—C7 | 1.433 (3) | C9—C10 | 1.384 (4) |
| C1—C2 | 1.391 (4) | C9—H9 | 0.9300 |
| C1—H1 | 0.9300 | C10—C11 | 1.393 (4) |
| C2—C3 | 1.371 (5) | C11—C12 | 1.380 (4) |
| C2—H2 | 0.9300 | C11—H11 | 0.9300 |
| C3—C4 | 1.380 (4) | C12—H12 | 0.9300 |
| C3—H3 | 0.9300 | ||
| N1—Cu1—N2 | 80.79 (9) | N1—C5—C4 | 122.1 (3) |
| N1—Cu1—Cl2 | 160.96 (7) | N1—C5—C6 | 115.0 (2) |
| N1—Cu1—Cl1 | 95.07 (7) | C4—C5—C6 | 122.8 (3) |
| N2—Cu1—Cl1 | 169.40 (7) | N2—C6—C5 | 119.2 (2) |
| N2—Cu1—Cl2 | 93.89 (6) | N2—C6—H6 | 120.4 |
| Cl1—Cu2—Cl1 | 93.05 (3) | C5—C6—H6 | 120.4 |
| C1—N1—C5 | 119.3 (2) | C8—C7—C12 | 119.5 (2) |
| C1—N1—Cu1 | 127.9 (2) | C8—C7—N2 | 122.2 (2) |
| C5—N1—Cu1 | 112.76 (17) | C12—C7—N2 | 118.3 (2) |
| C6—N2—C7 | 120.1 (2) | C7—C8—C9 | 120.5 (3) |
| C6—N2—Cu1 | 111.44 (18) | C7—C8—H8 | 119.8 |
| C7—N2—Cu1 | 128.50 (17) | C9—C8—H8 | 119.8 |
| N1—C1—C2 | 121.2 (3) | C10—C9—C8 | 119.5 (3) |
| N1—C1—H1 | 119.4 | C10—C9—H9 | 120.3 |
| C2—C1—H1 | 119.4 | C8—C9—H9 | 120.3 |
| C3—C2—C1 | 119.6 (3) | C9—C10—C11 | 120.4 (3) |
| C3—C2—H2 | 120.2 | C9—C10—I1 | 120.9 (2) |
| C1—C2—H2 | 120.2 | C11—C10—I1 | 118.7 (2) |
| C2—C3—C4 | 119.2 (3) | C12—C11—C10 | 119.8 (3) |
| C2—C3—H3 | 120.4 | C12—C11—H11 | 120.1 |
| C4—C3—H3 | 120.4 | C10—C11—H11 | 120.1 |
| C3—C4—C5 | 118.5 (3) | C11—C12—C7 | 120.3 (3) |
| C3—C4—H4 | 120.8 | C11—C12—H12 | 119.8 |
| C5—C4—H4 | 120.8 | C7—C12—H12 | 119.8 |
| N2—Cu1—N1—C1 | −175.5 (3) | C3—C4—C5—N1 | 1.4 (5) |
| Cl2—Cu1—N1—C1 | 109.5 (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—C5 | 8.14 (19) | Cu1—N2—C6—C5 | 3.6 (3) |
| Cl2—Cu1—N1—C5 | −66.8 (3) | N1—C5—C6—N2 | 3.3 (4) |
| Cl1—Cu1—N1—C5 | 178.30 (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—C6 | 155.25 (19) | Cu1—N2—C7—C8 | 151.3 (2) |
| Cl1—Cu1—N2—C6 | −74.0 (4) | C6—N2—C7—C12 | 148.2 (3) |
| N1—Cu1—N2—C7 | 172.9 (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—C7 | 105.3 (4) | N2—C7—C8—C9 | 177.4 (3) |
| C5—N1—C1—C2 | 2.6 (5) | C7—C8—C9—C10 | 1.1 (5) |
| Cu1—N1—C1—C2 | −173.5 (2) | C8—C9—C10—C11 | −0.8 (5) |
| N1—C1—C2—C3 | 0.6 (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—C5 | 1.9 (5) | I1—C10—C11—C12 | 177.1 (2) |
| C1—N1—C5—C4 | −3.7 (4) | C10—C11—C12—C7 | 1.0 (4) |
| Cu1—N1—C5—C4 | 173.0 (2) | C8—C7—C12—C11 | −0.8 (4) |
| C1—N1—C5—C6 | 174.7 (3) | N2—C7—C12—C11 | −178.6 (3) |
| Cu1—N1—C5—C6 | −8.6 (3) |
We thank the Islamic Azad University Research Council and the University of Malaya for supporting this study.
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.
Yamada, S. (1999). Coord. Chem. Rev. 190, 537–555.
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).