Acta Cryst. (2009). E65, m369 [ doi:10.1107/S1600536809007624 ]
In the title mononuclear copper(II) complex, [Cu(C7H5ClNO)2], the Cu atom, situated on an inversion center, is four-coordinated, in a slightly distorted square-planar geometry, by the N- and O-donor atoms of two symmetry-related 4-chloro-2-(iminomethyl)phenolate Schiff base ligands.
5-Chloro-2-hydroxybenzaldehyde (0.2 mmol, 31.3 mg), copper(II) acetate monohydrate (0.1 mmol, 20.0 mg) and three drops of ammonia (30%) were mixed in 10 ml of methanol. The final solution was stirred for 10 min and allowed to stand in air for two days, yielding blue needle-like crystals of the title compound.
The H-atoms were included in calculated positions and treated as riding: C-H = 0.93 Å, N-H = 0.86 Å, and Uiso(H) = 1.2Ueq(C,N).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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).
![[Figure 1]](./su2100fig1thm.gif)
| Fig. 1. The structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. |
| [Cu(C7H5ClNO)2] | F(000) = 374 |
| Mr = 372.68 | Dx = 1.751 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 15.775 (4) Å | Cell parameters from 811 reflections |
| b = 5.6949 (14) Å | θ = 2.5–24.3° |
| c = 7.886 (2) Å | µ = 1.93 mm−1 |
| β = 93.932 (3)° | T = 298 K |
| V = 706.8 (3) Å3 | Cut from needle, blue |
| Z = 2 | 0.18 × 0.17 × 0.17 mm |
| Bruker SMART CCD area-detector diffractometer | 1488 independent reflections |
| Radiation source: fine-focus sealed tube | 1025 reflections with I > 2σ(I) |
| graphite | Rint = 0.038 |
| ω scans | θmax = 26.7°, θmin = 2.6° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→19 |
| Tmin = 0.723, Tmax = 0.735 | k = −7→4 |
| 3835 measured reflections | l = −9→9 |
| 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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.139 | H-atom parameters constrained |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.0757P)2 + 0.0803P] where P = (Fo2 + 2Fc2)/3 |
| 1488 reflections | (Δ/σ)max < 0.001 |
| 97 parameters | Δρmax = 0.48 e Å−3 |
| 0 restraints | Δρmin = −0.57 e Å−3 |
| [Cu(C7H5ClNO)2] | V = 706.8 (3) Å3 |
| Mr = 372.68 | Z = 2 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 15.775 (4) Å | µ = 1.93 mm−1 |
| b = 5.6949 (14) Å | T = 298 K |
| c = 7.886 (2) Å | 0.18 × 0.17 × 0.17 mm |
| β = 93.932 (3)° |
| Bruker SMART CCD area-detector diffractometer | 1488 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1025 reflections with I > 2σ(I) |
| Tmin = 0.723, Tmax = 0.735 | Rint = 0.038 |
| 3835 measured reflections | θmax = 26.7° |
| R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
| wR(F2) = 0.139 | Δρmax = 0.48 e Å−3 |
| S = 1.01 | Δρmin = −0.57 e Å−3 |
| 1488 reflections | Absolute structure: ? |
| 97 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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. |
| x | y | z | Uiso*/Ueq | ||
| Cu1 | 0.5000 | 1.0000 | 1.0000 | 0.0394 (3) | |
| Cl1 | 0.93518 (8) | 0.8488 (3) | 0.8060 (2) | 0.0767 (5) | |
| N1 | 0.5411 (2) | 0.7404 (6) | 0.8909 (4) | 0.0407 (8) | |
| H1 | 0.5043 | 0.6336 | 0.8631 | 0.049* | |
| O1 | 0.60283 (17) | 1.1520 (5) | 1.0157 (4) | 0.0418 (7) | |
| C1 | 0.6875 (3) | 0.8577 (7) | 0.8857 (5) | 0.0361 (9) | |
| C2 | 0.6766 (3) | 1.0747 (7) | 0.9685 (5) | 0.0369 (9) | |
| C3 | 0.7494 (3) | 1.2131 (8) | 1.0047 (5) | 0.0446 (11) | |
| H3 | 0.7444 | 1.3543 | 1.0624 | 0.053* | |
| C4 | 0.8280 (3) | 1.1444 (8) | 0.9568 (6) | 0.0506 (12) | |
| H4 | 0.8751 | 1.2397 | 0.9817 | 0.061* | |
| C5 | 0.8372 (3) | 0.9355 (8) | 0.8721 (6) | 0.0468 (11) | |
| C6 | 0.7682 (3) | 0.7904 (8) | 0.8369 (6) | 0.0460 (11) | |
| H6 | 0.7749 | 0.6485 | 0.7811 | 0.055* | |
| C7 | 0.6171 (3) | 0.6979 (7) | 0.8509 (5) | 0.0411 (10) | |
| H7 | 0.6274 | 0.5568 | 0.7967 | 0.049* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cu1 | 0.0443 (5) | 0.0320 (4) | 0.0413 (5) | −0.0014 (3) | −0.0013 (3) | −0.0036 (3) |
| Cl1 | 0.0436 (7) | 0.0892 (11) | 0.0988 (12) | 0.0013 (7) | 0.0152 (7) | −0.0162 (9) |
| N1 | 0.041 (2) | 0.0338 (19) | 0.047 (2) | −0.0048 (15) | −0.0007 (16) | −0.0067 (15) |
| O1 | 0.0398 (17) | 0.0346 (17) | 0.0509 (18) | −0.0019 (12) | 0.0033 (13) | −0.0081 (13) |
| C1 | 0.041 (2) | 0.031 (2) | 0.036 (2) | −0.0007 (17) | −0.0005 (17) | 0.0020 (17) |
| C2 | 0.046 (3) | 0.031 (2) | 0.033 (2) | −0.0010 (18) | −0.0024 (18) | −0.0008 (16) |
| C3 | 0.051 (3) | 0.034 (2) | 0.048 (3) | −0.0038 (19) | −0.003 (2) | −0.0040 (18) |
| C4 | 0.042 (3) | 0.052 (3) | 0.057 (3) | −0.008 (2) | −0.001 (2) | 0.002 (2) |
| C5 | 0.037 (2) | 0.052 (3) | 0.051 (3) | 0.003 (2) | 0.004 (2) | 0.001 (2) |
| C6 | 0.051 (3) | 0.040 (3) | 0.048 (3) | 0.006 (2) | 0.004 (2) | 0.0001 (19) |
| C7 | 0.050 (3) | 0.030 (2) | 0.042 (2) | 0.0008 (18) | −0.0004 (19) | −0.0048 (18) |
| Cu1—O1i | 1.835 (3) | C1—C7 | 1.447 (6) |
| Cu1—O1 | 1.835 (3) | C2—C3 | 1.406 (6) |
| Cu1—N1i | 1.850 (3) | C3—C4 | 1.378 (6) |
| Cu1—N1 | 1.850 (3) | C3—H3 | 0.9300 |
| Cl1—C5 | 1.736 (5) | C4—C5 | 1.377 (7) |
| N1—C7 | 1.282 (5) | C4—H4 | 0.9300 |
| N1—H1 | 0.8600 | C5—C6 | 1.380 (6) |
| O1—C2 | 1.321 (5) | C6—H6 | 0.9300 |
| C1—C6 | 1.408 (6) | C7—H7 | 0.9300 |
| C1—C2 | 1.413 (6) | ||
| O1i—Cu1—O1 | 180.00 (8) | C4—C3—C2 | 121.6 (4) |
| O1i—Cu1—N1i | 94.10 (14) | C4—C3—H3 | 119.2 |
| O1—Cu1—N1i | 85.90 (14) | C2—C3—H3 | 119.2 |
| O1i—Cu1—N1 | 85.90 (14) | C5—C4—C3 | 120.3 (4) |
| O1—Cu1—N1 | 94.10 (14) | C5—C4—H4 | 119.8 |
| N1i—Cu1—N1 | 180.000 (1) | C3—C4—H4 | 119.8 |
| C7—N1—Cu1 | 128.9 (3) | C4—C5—C6 | 120.5 (4) |
| C7—N1—H1 | 115.5 | C4—C5—Cl1 | 121.1 (4) |
| Cu1—N1—H1 | 115.5 | C6—C5—Cl1 | 118.4 (4) |
| C2—O1—Cu1 | 128.0 (3) | C5—C6—C1 | 119.9 (4) |
| C6—C1—C2 | 120.3 (4) | C5—C6—H6 | 120.1 |
| C6—C1—C7 | 118.3 (4) | C1—C6—H6 | 120.1 |
| C2—C1—C7 | 121.4 (4) | N1—C7—C1 | 123.5 (4) |
| O1—C2—C3 | 118.6 (4) | N1—C7—H7 | 118.2 |
| O1—C2—C1 | 124.0 (4) | C1—C7—H7 | 118.2 |
| C3—C2—C1 | 117.4 (4) |
| Symmetry codes: (i) −x+1, −y+2, −z+2. |
Financial support from Jiaying University Research Fund is gratefully acknowledged.
Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Datta, A., Huang, J.-H. & Lee, H. M. (2008). Acta Cryst. E64, m1497.
Diallo, M., Tamboura, F. B., Gaye, M., Barry, A. H. & Bah, Y. (2008). Acta Cryst. E64, m1124–m1125.
Hong, Z. (2009). Acta Cryst. E65, m273.
Khalaji, A. D., Hadadzadeh, H., Gotoh, K. & Ishida, H. (2009). Acta Cryst. E65, m70.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Copper(II) complexes have been widely investigated in both bioinorganic chemistry and coordination chemistry (Diallo et al., 2008; Datta et al., 2008; Khalaji et al., 2009). As a further study of the structures of such complexes, the crystal structure of the title mononuclear copper(II) complex is reported here. The title complex is isostructural with the nickel(II) complex of the same ligand, 4-Chloro-2-(iminomethyl)phenolate, reported on recently by (Hong, 2009).
The molecular structure of the title complex is illustrated in Fig. 1, and geometrical parameters are given in the archived CIF. The CuII atom lies on an inversion center and is four-coordinated in a square-planar geometry by the N-and O-donor atoms of two Schiff base ligands. The whole molecule of the complex is approximately coplanar with mean deviation from the least-squares plane of 0.021 (2) Å.