Abstract
In the title centrosymmetric mononuclear complex, [Cu(C14H18NO2)2], the CuII ion, lying on an inversion centre, is four-coordinated by two imine N and two phenolate O atoms from two Schiff base ligands, forming a slightly distorted square-planar geometry.
Related literature
For general background to copper complexes, see: Collinson & Fenton (1996 ▶); Hossain et al. (1996 ▶); Tarafder et al. (2002 ▶); Musie et al. (2003 ▶); García-Raso et al. (2003 ▶); Reddy et al. (2000 ▶); Ray et al. (2003 ▶); Arnold et al. (2003 ▶); Raptopoulou et al. (1998 ▶). For related structures, see: Miao (2005 ▶, 2006 ▶); Wang (2007 ▶); Zhang (2004 ▶); Akitsu & Einaga (2004 ▶); Bluhm et al. (2003 ▶); Castillo et al. (2003 ▶); Lacroix et al. (2004 ▶).
Experimental
Crystal data
[Cu(C14H18NO2)2]
M r = 528.13
Monoclinic,
a = 6.4557 (10) Å
b = 11.5170 (17) Å
c = 17.074 (3) Å
β = 99.138 (2)°
V = 1253.4 (3) Å3
Z = 2
Mo Kα radiation
μ = 0.91 mm−1
T = 298 K
0.23 × 0.20 × 0.20 mm
Data collection
Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.818, T max = 0.839
6860 measured reflections
2727 independent reflections
2232 reflections with I > 2σ(I)
R int = 0.021
Refinement
R[F 2 > 2σ(F 2)] = 0.030
wR(F 2) = 0.080
S = 1.04
2727 reflections
161 parameters
H-atom parameters constrained
Δρmax = 0.28 e Å−3
Δρmin = −0.25 e Å−3
Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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.
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051629/ci2979sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051629/ci2979Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
The author acknowledges Baoji University of Arts and Sciences for funding this study (grant No. ZK0831).
supplementary crystallographic information
Comment
In the last few years there has been a burgeoning effort to identify the biological activities of copper, primarily through techniques associated with the interface of biology/biochemistry/coordination chemistry (Collinson & Fenton, 1996; Hossain et al., 1996; Tarafder et al., 2002). It appears that the biological role of copper is primarily in redox reactions and as a biological catalyst, although much remains to be understood (Musie et al., 2003; García-Raso et al., 2003). An extensive effort has been made to prepare and characterize a variety of copper(II) coordination complexes in an attempt to model the physical and chemical behaviour of copper-containing enzymes (Reddy et al., 2000). The peculiarity of copper lies in its ability to form complexes with coordination number four, five or six (Ray et al., 2003; Arnold et al., 2003; Raptopoulou et al., 1998). As an extension of the work on the structural characterization of such complexes (Miao, 2005, 2006), the crystal structure of the title new mononuclear copper(II) compound, is reported here.
The compound is a centrosymmetric mononuclear copper(II) complex, as shown in Fig. 1. The CuII ion, lying on an inversion centre, is four-coordinated by two imine N and two phenolate O atoms from two Schiff base ligands, forming a square-planar geometry. The Cu—O and Cu—N bond lengths are comparable with those reported in similar structures (Wang, 2007; Zhang, 2004; Akitsu & Einaga, 2004; Bluhm et al., 2003; Castillo et al., 2003; Lacroix et al., 2004). Both cyclohexane rings adopt chair conformations.
Experimental
4-Methoxysalicylaldehyde (1 mmol, 152 mg), cyclohexylamine (1 mmol, 99 mg) and Cu(CH3COO)2.H2O (0.5 mmol, 100 mg) were dissolved in methanol (50 ml). The mixture was stirred at room temperature for 1 h to give a blue solution. The resulting solution was kept in air for 5 d, and block blue crystals were formed.
Refinement
H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å, and with Uiso(H) = 1.2 or 1.5Ueq(C).
Figures
Fig. 1.
The molecular structure of the title compound, showing 30% displacement ellipsoids (arbitrary spheres for the H atoms). Unlabelled atoms are at the symmetry position (-x, -y, -z).
Crystal data
| [Cu(C14H18NO2)2] | F(000) = 558 |
| Mr = 528.13 | Dx = 1.399 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 2706 reflections |
| a = 6.4557 (10) Å | θ = 2.4–28.7° |
| b = 11.5170 (17) Å | µ = 0.91 mm−1 |
| c = 17.074 (3) Å | T = 298 K |
| β = 99.138 (2)° | Block, blue |
| V = 1253.4 (3) Å3 | 0.23 × 0.20 × 0.20 mm |
| Z = 2 |
Data collection
| Bruker SMART CCD area-detector diffractometer | 2727 independent reflections |
| Radiation source: fine-focus sealed tube | 2232 reflections with I > 2σ(I) |
| graphite | Rint = 0.021 |
| ω scans | θmax = 27.0°, θmin = 2.1° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→8 |
| Tmin = 0.818, Tmax = 0.839 | k = −14→14 |
| 6860 measured reflections | l = −17→21 |
Refinement
| 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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.080 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0393P)2 + 0.3443P] where P = (Fo2 + 2Fc2)/3 |
| 2727 reflections | (Δ/σ)max = 0.001 |
| 161 parameters | Δρmax = 0.28 e Å−3 |
| 0 restraints | Δρmin = −0.25 e Å−3 |
Special details
| 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Cu1 | 0.0000 | 0.0000 | 0.0000 | 0.02741 (11) | |
| N1 | 0.2825 (2) | −0.05099 (13) | 0.05759 (8) | 0.0279 (3) | |
| O1 | −0.02292 (18) | 0.11030 (12) | 0.08083 (8) | 0.0369 (3) | |
| O2 | 0.2183 (2) | 0.44832 (13) | 0.22866 (8) | 0.0435 (3) | |
| C1 | 0.3444 (3) | 0.13149 (15) | 0.12935 (10) | 0.0293 (4) | |
| C2 | 0.1333 (3) | 0.17066 (15) | 0.11880 (10) | 0.0290 (4) | |
| C3 | 0.0893 (3) | 0.27716 (16) | 0.15350 (11) | 0.0324 (4) | |
| H3 | −0.0488 | 0.3025 | 0.1492 | 0.039* | |
| C4 | 0.2490 (3) | 0.34426 (15) | 0.19372 (10) | 0.0321 (4) | |
| C5 | 0.4579 (3) | 0.30770 (17) | 0.20160 (12) | 0.0377 (4) | |
| H5 | 0.5654 | 0.3543 | 0.2271 | 0.045* | |
| C6 | 0.5013 (3) | 0.20248 (16) | 0.17120 (11) | 0.0350 (4) | |
| H6 | 0.6396 | 0.1769 | 0.1784 | 0.042* | |
| C7 | 0.4013 (3) | 0.01873 (15) | 0.10362 (11) | 0.0314 (4) | |
| H7 | 0.5373 | −0.0064 | 0.1220 | 0.038* | |
| C8 | 0.3570 (3) | −0.17037 (15) | 0.04404 (11) | 0.0292 (4) | |
| H8 | 0.3409 | −0.1818 | −0.0135 | 0.035* | |
| C9 | 0.5849 (3) | −0.19822 (16) | 0.07803 (12) | 0.0344 (4) | |
| H9A | 0.6775 | −0.1459 | 0.0555 | 0.041* | |
| H9B | 0.6075 | −0.1871 | 0.1351 | 0.041* | |
| C10 | 0.6355 (3) | −0.32350 (17) | 0.05889 (14) | 0.0425 (5) | |
| H10A | 0.7792 | −0.3409 | 0.0820 | 0.051* | |
| H10B | 0.6229 | −0.3327 | 0.0019 | 0.051* | |
| C11 | 0.4882 (3) | −0.40877 (17) | 0.09089 (14) | 0.0448 (5) | |
| H11A | 0.5208 | −0.4873 | 0.0763 | 0.054* | |
| H11B | 0.5082 | −0.4041 | 0.1483 | 0.054* | |
| C12 | 0.2621 (3) | −0.38098 (17) | 0.05739 (14) | 0.0455 (5) | |
| H12A | 0.1699 | −0.4333 | 0.0801 | 0.055* | |
| H12B | 0.2392 | −0.3927 | 0.0004 | 0.055* | |
| C13 | 0.2090 (3) | −0.25579 (16) | 0.07562 (13) | 0.0389 (4) | |
| H13A | 0.2194 | −0.2461 | 0.1325 | 0.047* | |
| H13B | 0.0656 | −0.2391 | 0.0517 | 0.047* | |
| C14 | 0.0085 (4) | 0.48443 (19) | 0.23134 (17) | 0.0591 (7) | |
| H14A | −0.0676 | 0.4892 | 0.1784 | 0.089* | |
| H14B | 0.0100 | 0.5592 | 0.2562 | 0.089* | |
| H14C | −0.0583 | 0.4292 | 0.2612 | 0.089* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cu1 | 0.02394 (16) | 0.02709 (17) | 0.02975 (17) | 0.00081 (12) | −0.00020 (11) | −0.00354 (12) |
| N1 | 0.0262 (7) | 0.0262 (7) | 0.0306 (8) | 0.0021 (6) | 0.0025 (6) | 0.0001 (6) |
| O1 | 0.0262 (6) | 0.0415 (7) | 0.0409 (7) | 0.0005 (5) | −0.0011 (5) | −0.0141 (6) |
| O2 | 0.0426 (8) | 0.0368 (8) | 0.0501 (8) | −0.0028 (6) | 0.0043 (6) | −0.0145 (7) |
| C1 | 0.0277 (9) | 0.0301 (9) | 0.0289 (9) | −0.0006 (7) | 0.0011 (7) | −0.0003 (7) |
| C2 | 0.0281 (9) | 0.0321 (9) | 0.0260 (8) | −0.0018 (7) | 0.0018 (7) | 0.0001 (7) |
| C3 | 0.0274 (9) | 0.0356 (10) | 0.0335 (9) | 0.0023 (7) | 0.0024 (7) | −0.0039 (8) |
| C4 | 0.0396 (10) | 0.0278 (9) | 0.0287 (9) | −0.0018 (8) | 0.0045 (8) | −0.0017 (7) |
| C5 | 0.0327 (10) | 0.0374 (11) | 0.0412 (11) | −0.0090 (8) | −0.0001 (8) | −0.0053 (9) |
| C6 | 0.0269 (9) | 0.0371 (10) | 0.0393 (10) | −0.0012 (8) | 0.0005 (7) | −0.0015 (8) |
| C7 | 0.0251 (9) | 0.0355 (10) | 0.0325 (9) | 0.0015 (7) | 0.0014 (7) | 0.0025 (7) |
| C8 | 0.0275 (9) | 0.0278 (9) | 0.0322 (9) | 0.0027 (7) | 0.0040 (7) | 0.0009 (7) |
| C9 | 0.0280 (9) | 0.0311 (10) | 0.0439 (11) | 0.0013 (7) | 0.0047 (8) | 0.0026 (8) |
| C10 | 0.0333 (10) | 0.0361 (11) | 0.0592 (13) | 0.0076 (8) | 0.0107 (9) | 0.0050 (9) |
| C11 | 0.0474 (12) | 0.0291 (10) | 0.0588 (13) | 0.0049 (9) | 0.0115 (10) | 0.0069 (9) |
| C12 | 0.0433 (11) | 0.0317 (10) | 0.0634 (14) | −0.0039 (9) | 0.0143 (10) | 0.0029 (10) |
| C13 | 0.0297 (9) | 0.0347 (10) | 0.0537 (12) | −0.0009 (8) | 0.0111 (8) | 0.0024 (9) |
| C14 | 0.0502 (13) | 0.0549 (15) | 0.0724 (17) | 0.0048 (11) | 0.0106 (12) | −0.0306 (12) |
Geometric parameters (Å, °)
| Cu1—O1i | 1.8987 (12) | C8—C9 | 1.527 (2) |
| Cu1—O1 | 1.8987 (12) | C8—C13 | 1.528 (2) |
| Cu1—N1i | 2.0169 (14) | C8—H8 | 0.98 |
| Cu1—N1 | 2.0169 (14) | C9—C10 | 1.526 (3) |
| N1—C7 | 1.288 (2) | C9—H9A | 0.97 |
| N1—C8 | 1.487 (2) | C9—H9B | 0.97 |
| O1—C2 | 1.309 (2) | C10—C11 | 1.527 (3) |
| O2—C4 | 1.367 (2) | C10—H10A | 0.97 |
| O2—C14 | 1.424 (3) | C10—H10B | 0.97 |
| C1—C6 | 1.406 (2) | C11—C12 | 1.515 (3) |
| C1—C2 | 1.420 (2) | C11—H11A | 0.97 |
| C1—C7 | 1.437 (2) | C11—H11B | 0.97 |
| C2—C3 | 1.411 (2) | C12—C13 | 1.525 (3) |
| C3—C4 | 1.381 (2) | C12—H12A | 0.97 |
| C3—H3 | 0.93 | C12—H12B | 0.97 |
| C4—C5 | 1.399 (3) | C13—H13A | 0.97 |
| C5—C6 | 1.365 (3) | C13—H13B | 0.97 |
| C5—H5 | 0.93 | C14—H14A | 0.96 |
| C6—H6 | 0.93 | C14—H14B | 0.96 |
| C7—H7 | 0.93 | C14—H14C | 0.96 |
| O1i—Cu1—O1 | 180.00 (10) | C13—C8—H8 | 107.1 |
| O1i—Cu1—N1i | 90.53 (5) | C10—C9—C8 | 110.06 (15) |
| O1—Cu1—N1i | 89.47 (5) | C10—C9—H9A | 109.6 |
| O1i—Cu1—N1 | 89.47 (5) | C8—C9—H9A | 109.6 |
| O1—Cu1—N1 | 90.53 (5) | C10—C9—H9B | 109.6 |
| N1i—Cu1—N1 | 180.00 (11) | C8—C9—H9B | 109.6 |
| C7—N1—C8 | 119.69 (15) | H9A—C9—H9B | 108.2 |
| C7—N1—Cu1 | 121.37 (12) | C9—C10—C11 | 111.40 (16) |
| C8—N1—Cu1 | 118.90 (11) | C9—C10—H10A | 109.3 |
| C2—O1—Cu1 | 124.93 (11) | C11—C10—H10A | 109.3 |
| C4—O2—C14 | 118.32 (15) | C9—C10—H10B | 109.3 |
| C6—C1—C2 | 118.65 (16) | C11—C10—H10B | 109.3 |
| C6—C1—C7 | 118.84 (16) | H10A—C10—H10B | 108.0 |
| C2—C1—C7 | 122.36 (16) | C12—C11—C10 | 110.27 (17) |
| O1—C2—C3 | 118.64 (15) | C12—C11—H11A | 109.6 |
| O1—C2—C1 | 122.87 (16) | C10—C11—H11A | 109.6 |
| C3—C2—C1 | 118.44 (16) | C12—C11—H11B | 109.6 |
| C4—C3—C2 | 120.76 (16) | C10—C11—H11B | 109.6 |
| C4—C3—H3 | 119.6 | H11A—C11—H11B | 108.1 |
| C2—C3—H3 | 119.6 | C11—C12—C13 | 110.90 (17) |
| O2—C4—C3 | 124.00 (17) | C11—C12—H12A | 109.5 |
| O2—C4—C5 | 115.23 (16) | C13—C12—H12A | 109.5 |
| C3—C4—C5 | 120.77 (17) | C11—C12—H12B | 109.5 |
| C6—C5—C4 | 118.93 (17) | C13—C12—H12B | 109.5 |
| C6—C5—H5 | 120.5 | H12A—C12—H12B | 108.0 |
| C4—C5—H5 | 120.5 | C12—C13—C8 | 111.31 (15) |
| C5—C6—C1 | 122.33 (17) | C12—C13—H13A | 109.4 |
| C5—C6—H6 | 118.8 | C8—C13—H13A | 109.4 |
| C1—C6—H6 | 118.8 | C12—C13—H13B | 109.4 |
| N1—C7—C1 | 126.40 (17) | C8—C13—H13B | 109.4 |
| N1—C7—H7 | 116.8 | H13A—C13—H13B | 108.0 |
| C1—C7—H7 | 116.8 | O2—C14—H14A | 109.5 |
| N1—C8—C9 | 116.81 (14) | O2—C14—H14B | 109.5 |
| N1—C8—C13 | 107.74 (13) | H14A—C14—H14B | 109.5 |
| C9—C8—C13 | 110.43 (15) | O2—C14—H14C | 109.5 |
| N1—C8—H8 | 107.1 | H14A—C14—H14C | 109.5 |
| C9—C8—H8 | 107.1 | H14B—C14—H14C | 109.5 |
Symmetry codes: (i) −x, −y, −z.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2979).
References
- Akitsu, T. & Einaga, Y. (2004). Acta Cryst. E60, m436–m438.
- Arnold, P. J., Davies, S. C., Durrant, M. C., Griffiths, D. V., Hughes, D. L. & Sharpe, P. C. (2003). Inorg. Chim. Acta, 348, 143–149.
- Bluhm, M. E., Ciesielski, M., Görls, H., Walter, O. & Döring, M. (2003). Inorg. Chem.42, 8878–8885. [DOI] [PubMed]
- Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
- Castillo, I., Fernández-González, J. M. & Gárate-Morales, J. L. (2003). J. Mol. Struct.657, 25–35.
- Collinson, S. R. & Fenton, D. E. (1996). Coord. Chem. Rev.148, 19–40.
- García-Raso, Á., Fiol, J. J., López-Zafra, A., Castro, J. A., Cabrero, A., Mata, I. & Molins, E. (2003). Polyhedron, 22, 403–409.
- Hossain, M. E., Alam, M. N., Begum, J., Ali, M. A., Nazimuddin, M., Smith, F. E. & Hynes, R. C. (1996). Inorg. Chim. Acta, 249, 207–213.
- Lacroix, P. G., Averseng, F., Malfant, I. & Nakatani, K. (2004). Inorg. Chim. Acta, 357, 3825–3835.
- Miao, J.-Y. (2005). Acta Cryst. E61, m1981–m1983.
- Miao, J.-Y. (2006). Acta Cryst. E62, m3112–m3114.
- Musie, G. T., Li, X. & Powell, D. R. (2003). Inorg. Chim. Acta, 348, 69–74.
- Raptopoulou, C. P., Papadopoulos, A. N., Malamatari, D. A., Ioannidis, E., Moisidis, G., Terzis, A. & Kessissoglou, D. P. (1998). Inorg. Chim. Acta, 272, 283–290.
- Ray, M. S., Bhattacharya, R. B., Chaudhuri, S., Righi, L., Bocelli, G., Mukhopadhyay, G. & Ghosh, A. (2003). Polyhedron, 22, 617–624.
- Reddy, P. A. N., Datta, R. & Chakravarty, A. R. (2000). Inorg. Chem. Commun.3, 322–324.
- Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Tarafder, M. T. H., Jin, K. T., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H.-K. (2002). Polyhedron, 21, 2547–2554.
- Wang, C.-Y. (2007). Acta Cryst. E63, m489–m491.
- Zhang, P. (2004). Acta Cryst. E60, m1808–m1810.
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051629/ci2979sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051629/ci2979Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report

