Acta Cryst. (2009). E65, m339 [ doi:10.1107/S1600536809006606 ]
The title compound, [Cu(C12H13BrNO)2], was prepared by the reaction of 5-bromosalicylaldehyde, cyclopentylamine and copper(II) acetate in an ethanol solution. The CuII atom lies on an inversion center and is four-coordinated in a square-planar geometry by two N and two O atoms from two 4-bromo-2-(cyclopentyliminomethyl)phenolate Schiff base ligands.
5-Bromosalicylaldehyde (0.2 mmol, 40.3 mg), cyclopentylamine (0.2 mmol, 17.0 mg), and copper(II) acetate monohydrate (0.1 mmol, 20.0 mg) were mixed in 20 ml of ethanol. The mixture was stirred for 2 h at rt, giving a blue solution. Single-crystals were formed by gradual evaporation of the solution in air after several days.
H atoms were placed in calculated positions and treated as riding: C–H = 0.93–0.98 Å, with Uiso(H) = 1.2Ueq(C).
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]](./su2099fig1thm.gif)
| Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids [unlabelled atoms are related to the labelled atoms by the symmetry operation -x, 2-y, -z]. |
| [Cu(C12H13BrNO)2] | F(000) = 598 |
| Mr = 597.83 | Dx = 1.721 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 9.190 (2) Å | Cell parameters from 2505 reflections |
| b = 10.960 (2) Å | θ = 2.3–25.0° |
| c = 12.166 (2) Å | µ = 4.43 mm−1 |
| β = 109.73 (3)° | T = 298 K |
| V = 1153.5 (4) Å3 | Block, blue |
| Z = 2 | 0.27 × 0.23 × 0.23 mm |
| Bruker SMART 1000 CCD area-detector diffractometer | 2636 independent reflections |
| Radiation source: fine-focus sealed tube | 2003 reflections with I > 2σ(I) |
| graphite | Rint = 0.035 |
| ω scans | θmax = 27.5°, θmin = 2.4° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
| Tmin = 0.381, Tmax = 0.429 | k = −14→14 |
| 9709 measured reflections | l = −15→15 |
| 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.098 | H-atom parameters constrained |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.0427P)2 + 0.9221P] where P = (Fo2 + 2Fc2)/3 |
| 2636 reflections | (Δ/σ)max = 0.001 |
| 142 parameters | Δρmax = 0.93 e Å−3 |
| 0 restraints | Δρmin = −0.41 e Å−3 |
| [Cu(C12H13BrNO)2] | V = 1153.5 (4) Å3 |
| Mr = 597.83 | Z = 2 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 9.190 (2) Å | µ = 4.43 mm−1 |
| b = 10.960 (2) Å | T = 298 K |
| c = 12.166 (2) Å | 0.27 × 0.23 × 0.23 mm |
| β = 109.73 (3)° |
| Bruker SMART 1000 CCD area-detector diffractometer | 2636 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2003 reflections with I > 2σ(I) |
| Tmin = 0.381, Tmax = 0.429 | Rint = 0.035 |
| 9709 measured reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.098 | Δρmax = 0.93 e Å−3 |
| S = 1.02 | Δρmin = −0.41 e Å−3 |
| 2636 reflections | Absolute structure: ? |
| 142 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 > 2sigma(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 | 0.0000 | 1.0000 | 0.0000 | 0.03400 (16) | |
| Br1 | −0.34783 (5) | 0.60773 (4) | 0.33661 (4) | 0.06123 (17) | |
| O1 | −0.0883 (3) | 1.00623 (19) | 0.1197 (2) | 0.0446 (6) | |
| N1 | 0.0534 (3) | 0.8203 (2) | 0.0328 (2) | 0.0341 (6) | |
| C1 | −0.1071 (4) | 0.7941 (3) | 0.1548 (3) | 0.0344 (7) | |
| C2 | −0.1456 (4) | 0.9175 (3) | 0.1630 (3) | 0.0348 (7) | |
| C3 | −0.2475 (4) | 0.9435 (3) | 0.2236 (3) | 0.0435 (8) | |
| H3 | −0.2753 | 1.0242 | 0.2294 | 0.052* | |
| C4 | −0.3073 (4) | 0.8541 (3) | 0.2744 (3) | 0.0465 (9) | |
| H4 | −0.3752 | 0.8741 | 0.3136 | 0.056* | |
| C5 | −0.2659 (4) | 0.7337 (3) | 0.2671 (3) | 0.0422 (8) | |
| C6 | −0.1676 (4) | 0.7034 (3) | 0.2090 (3) | 0.0391 (7) | |
| H6 | −0.1404 | 0.6222 | 0.2052 | 0.047* | |
| C7 | −0.0063 (4) | 0.7551 (3) | 0.0935 (3) | 0.0374 (7) | |
| H7 | 0.0184 | 0.6726 | 0.0987 | 0.045* | |
| C8 | 0.1560 (4) | 0.7602 (3) | −0.0219 (3) | 0.0386 (7) | |
| H8 | 0.1265 | 0.7915 | −0.1019 | 0.046* | |
| C9 | 0.3252 (4) | 0.7923 (4) | 0.0374 (4) | 0.0603 (11) | |
| H9A | 0.3467 | 0.8740 | 0.0163 | 0.072* | |
| H9B | 0.3536 | 0.7874 | 0.1216 | 0.072* | |
| C10 | 0.4115 (5) | 0.6976 (5) | −0.0078 (6) | 0.0901 (18) | |
| H10A | 0.4543 | 0.7346 | −0.0626 | 0.108* | |
| H10B | 0.4955 | 0.6632 | 0.0563 | 0.108* | |
| C11 | 0.2977 (5) | 0.6002 (4) | −0.0671 (4) | 0.0642 (12) | |
| H11A | 0.3412 | 0.5199 | −0.0429 | 0.077* | |
| H11B | 0.2696 | 0.6065 | −0.1512 | 0.077* | |
| C12 | 0.1586 (5) | 0.6206 (3) | −0.0307 (4) | 0.0507 (9) | |
| H12A | 0.1713 | 0.5824 | 0.0438 | 0.061* | |
| H12B | 0.0651 | 0.5900 | −0.0889 | 0.061* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cu1 | 0.0412 (3) | 0.0242 (3) | 0.0424 (3) | 0.0024 (2) | 0.0218 (3) | 0.0028 (2) |
| Br1 | 0.0702 (3) | 0.0547 (3) | 0.0720 (3) | −0.0114 (2) | 0.0414 (2) | 0.0125 (2) |
| O1 | 0.0659 (16) | 0.0251 (11) | 0.0570 (15) | 0.0009 (11) | 0.0395 (13) | 0.0012 (10) |
| N1 | 0.0374 (14) | 0.0263 (13) | 0.0425 (15) | 0.0034 (11) | 0.0185 (12) | 0.0018 (11) |
| C1 | 0.0377 (17) | 0.0294 (16) | 0.0387 (17) | 0.0018 (13) | 0.0163 (14) | 0.0037 (13) |
| C2 | 0.0401 (18) | 0.0290 (15) | 0.0373 (17) | 0.0023 (13) | 0.0159 (14) | 0.0031 (13) |
| C3 | 0.056 (2) | 0.0336 (17) | 0.050 (2) | 0.0058 (16) | 0.0300 (18) | −0.0006 (16) |
| C4 | 0.050 (2) | 0.049 (2) | 0.049 (2) | 0.0019 (17) | 0.0287 (18) | 0.0009 (17) |
| C5 | 0.0443 (19) | 0.0424 (19) | 0.0442 (19) | −0.0079 (15) | 0.0205 (16) | 0.0070 (15) |
| C6 | 0.0461 (19) | 0.0289 (16) | 0.0441 (19) | −0.0008 (14) | 0.0175 (15) | 0.0036 (14) |
| C7 | 0.0406 (17) | 0.0270 (16) | 0.0470 (19) | 0.0064 (13) | 0.0177 (15) | 0.0040 (14) |
| C8 | 0.0421 (18) | 0.0292 (16) | 0.0489 (19) | 0.0060 (14) | 0.0212 (16) | 0.0012 (14) |
| C9 | 0.043 (2) | 0.056 (2) | 0.085 (3) | −0.0012 (19) | 0.026 (2) | −0.024 (2) |
| C10 | 0.051 (3) | 0.082 (3) | 0.147 (5) | −0.006 (2) | 0.046 (3) | −0.051 (4) |
| C11 | 0.066 (3) | 0.049 (2) | 0.085 (3) | 0.012 (2) | 0.036 (2) | −0.010 (2) |
| C12 | 0.059 (2) | 0.0349 (19) | 0.064 (2) | 0.0030 (17) | 0.028 (2) | −0.0058 (17) |
| Cu1—O1i | 1.892 (2) | C6—H6 | 0.9300 |
| Cu1—O1 | 1.892 (2) | C7—H7 | 0.9300 |
| Cu1—N1 | 2.036 (2) | C8—C9 | 1.518 (5) |
| Cu1—N1i | 2.036 (2) | C8—C12 | 1.534 (4) |
| Br1—C5 | 1.902 (3) | C8—H8 | 0.9800 |
| O1—C2 | 1.299 (4) | C9—C10 | 1.518 (5) |
| N1—C7 | 1.278 (4) | C9—H9A | 0.9700 |
| N1—C8 | 1.480 (4) | C9—H9B | 0.9700 |
| C1—C6 | 1.407 (4) | C10—C11 | 1.498 (6) |
| C1—C2 | 1.411 (4) | C10—H10A | 0.9700 |
| C1—C7 | 1.436 (4) | C10—H10B | 0.9700 |
| C2—C3 | 1.403 (4) | C11—C12 | 1.504 (6) |
| C3—C4 | 1.369 (5) | C11—H11A | 0.9700 |
| C3—H3 | 0.9300 | C11—H11B | 0.9700 |
| C4—C5 | 1.385 (5) | C12—H12A | 0.9700 |
| C4—H4 | 0.9300 | C12—H12B | 0.9700 |
| C5—C6 | 1.362 (5) | ||
| O1i—Cu1—O1 | 180.0 | N1—C8—C9 | 112.9 (3) |
| O1i—Cu1—N1 | 88.74 (10) | N1—C8—C12 | 120.2 (3) |
| O1—Cu1—N1 | 91.26 (10) | C9—C8—C12 | 103.1 (3) |
| O1i—Cu1—N1i | 91.26 (10) | N1—C8—H8 | 106.6 |
| O1—Cu1—N1i | 88.74 (10) | C9—C8—H8 | 106.6 |
| N1—Cu1—N1i | 180.0 | C12—C8—H8 | 106.6 |
| C2—O1—Cu1 | 128.5 (2) | C10—C9—C8 | 104.2 (3) |
| C7—N1—C8 | 118.3 (3) | C10—C9—H9A | 110.9 |
| C7—N1—Cu1 | 122.1 (2) | C8—C9—H9A | 110.9 |
| C8—N1—Cu1 | 119.42 (19) | C10—C9—H9B | 110.9 |
| C6—C1—C2 | 119.7 (3) | C8—C9—H9B | 110.9 |
| C6—C1—C7 | 117.4 (3) | H9A—C9—H9B | 108.9 |
| C2—C1—C7 | 122.9 (3) | C11—C10—C9 | 107.3 (3) |
| O1—C2—C3 | 119.7 (3) | C11—C10—H10A | 110.3 |
| O1—C2—C1 | 122.9 (3) | C9—C10—H10A | 110.3 |
| C3—C2—C1 | 117.3 (3) | C11—C10—H10B | 110.3 |
| C4—C3—C2 | 122.3 (3) | C9—C10—H10B | 110.3 |
| C4—C3—H3 | 118.9 | H10A—C10—H10B | 108.5 |
| C2—C3—H3 | 118.9 | C10—C11—C12 | 106.1 (3) |
| C3—C4—C5 | 119.5 (3) | C10—C11—H11A | 110.5 |
| C3—C4—H4 | 120.3 | C12—C11—H11A | 110.5 |
| C5—C4—H4 | 120.3 | C10—C11—H11B | 110.5 |
| C6—C5—C4 | 120.7 (3) | C12—C11—H11B | 110.5 |
| C6—C5—Br1 | 119.0 (3) | H11A—C11—H11B | 108.7 |
| C4—C5—Br1 | 120.3 (3) | C11—C12—C8 | 101.8 (3) |
| C5—C6—C1 | 120.5 (3) | C11—C12—H12A | 111.4 |
| C5—C6—H6 | 119.7 | C8—C12—H12A | 111.4 |
| C1—C6—H6 | 119.7 | C11—C12—H12B | 111.4 |
| N1—C7—C1 | 127.8 (3) | C8—C12—H12B | 111.4 |
| N1—C7—H7 | 116.1 | H12A—C12—H12B | 109.3 |
| C1—C7—H7 | 116.1 |
| Symmetry codes: (i) −x, −y+2, −z. |
Ali, H. M., Puvaneswary, S. & Ng, S. W. (2006). Acta Cryst. E62, m2737–m2738.
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cai, B.-H. (2009). Acta Cryst. E65, m142.
Costes, J.-P., Clemente-Juan, J. M., Dahan, F., Dumestre, F. & Tuchagues, J.-P. (2002). Inorg. Chem. 41, 2886–2891.
Datta, A., Huang, J.-H. & Lee, H. M. (2008). Acta Cryst. E64, m1497.
Erxleben, A. (2001). Inorg. Chem. 40, 208–213.
Lacroix, P. G., Di Bella, S. & Ledoux, I. (1996). Chem. Mater. 8, 541–545.
Odoko, M., Tsuchida, N. & Okabe, N. (2006). Acta Cryst. E62, m710–m711.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Wang, L., Dong, J.-F., Li, L.-Z., Li, L.-W. & Wang, D.-Q. (2007). Acta Cryst. E63, m1059–m1060.
Wang, L.-G. & Zheng, Y.-F. (2007). Acta Cryst. E63, m390–m391.
Yusnita, J., Ali, H. M., Puvaneswary, S., Robinson, W. T. & Ng, S. W. (2008). Acta Cryst. E64, m1039.
Schiff bases are interesting ligands which form a large number of complexes with metal atoms (Costes et al., 2002; Erxleben, 2001; Lacroix et al., 1996; Odoko et al., 2006; Ali et al., 2006). The author has recently reported on the crystal structure of a zinc(II) complex with the Schiff base (2-morpholin-4-ylethyl)-(1-pyridin-2-ylmethylidene)amine (Cai, 2009). As a continuous of our work in this area, we report here on the crystal structure of the title copper(II) complex (Fig. 1), derived from the Schiff base 4-bromo-2-(cyclopentyliminomethyl)phenol.
In the centrosymmetric title complex the CuII atom, is located on an inversion center, and is four-coordinate in a square planar geometry with two nitrogen and two oxygen atoms from two Schiff base ligands. All the coordinate bond lengths are typical and comparable with those in similar copper(II) complexes (Wang et al., 2007; Datta et al., 2008; Yusnita et al., 2008; Wang & Zheng, 2007).