Acta Cryst. (2007). E63, m1766 [ doi:10.1107/S1600536807023860 ]
The title complex, [Cu(C13H16NO2)2], is a mononuclear copper(II) complex. The Cu atom is located on a crystallographic inversion centre and is coordinated by two O and two N atoms from two Schiff base ligands, forming a square-planar geometry.
3-Methoxy-2-hydroxybenzaldehyde (0.2 mmol, 30.5 mg), cyclopentylamine (0.2 mmol, 17.2 mg), and Cu(CH3COO)2.H2O (0.1 mmol, 20.0 mg) were dissolved in methanol. The mixture was stirred at 325 K for 30 min to give a transparent blue solution. Blue crystals were obtained by slow evaporation of the solution in air.
H atoms were positioned geometrically and refined as riding atoms, with C–H distances in the range 0.93–0.97 Å and Uiso(H) set at 1.2Ueq(C) and 1.5Ueq(methyl C).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
![[Figure 1]](./gk2077fig1thm.gif)
| Fig. 1. The molecular structure of (I), with anisotropic displacement ellipsoids drawn at the 30% probability level. |
| [Cu(C13H16NO2)2] | F(000) = 1052 |
| Mr = 500.08 | Dx = 1.427 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 3071 reflections |
| a = 12.060 (2) Å | θ = 2.3–25.4° |
| b = 10.8025 (18) Å | µ = 0.97 mm−1 |
| c = 17.863 (3) Å | T = 293 K |
| V = 2327.1 (7) Å3 | Block, blue |
| Z = 4 | 0.33 × 0.27 × 0.25 mm |
| Bruker SMART APEX CCD area-detector diffractometer | 2662 independent reflections |
| Radiation source: fine-focus sealed tube | 1921 reflections with I > 2σ(I) |
| graphite | Rint = 0.048 |
| ω scans | θmax = 27.5°, θmin = 2.3° |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −15→15 |
| Tmin = 0.739, Tmax = 0.793 | k = −13→13 |
| 18677 measured reflections | l = −22→22 |
| 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) = 0.108 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0539P)2 + 0.5523P] where P = (Fo2 + 2Fc2)/3 |
| 2662 reflections | (Δ/σ)max < 0.001 |
| 152 parameters | Δρmax = 0.28 e Å−3 |
| 0 restraints | Δρmin = −0.52 e Å−3 |
| [Cu(C13H16NO2)2] | V = 2327.1 (7) Å3 |
| Mr = 500.08 | Z = 4 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 12.060 (2) Å | µ = 0.97 mm−1 |
| b = 10.8025 (18) Å | T = 293 K |
| c = 17.863 (3) Å | 0.33 × 0.27 × 0.25 mm |
| Bruker SMART APEX CCD area-detector diffractometer | 2662 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1921 reflections with I > 2σ(I) |
| Tmin = 0.739, Tmax = 0.793 | Rint = 0.048 |
| 18677 measured reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.108 | Δρmax = 0.28 e Å−3 |
| S = 1.03 | Δρmin = −0.52 e Å−3 |
| 2662 reflections | Absolute structure: ? |
| 152 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 | 0.5000 | 0.03149 (14) | |
| O1 | 0.48094 (13) | 1.06065 (17) | 0.59762 (9) | 0.0476 (4) | |
| O2 | 0.47911 (14) | 1.21263 (17) | 0.71126 (10) | 0.0532 (5) | |
| N1 | 0.37204 (14) | 0.88125 (16) | 0.51335 (9) | 0.0309 (4) | |
| C1 | 0.30127 (18) | 0.98086 (19) | 0.62636 (12) | 0.0349 (5) | |
| C2 | 0.39230 (17) | 1.05894 (19) | 0.63916 (11) | 0.0339 (5) | |
| C3 | 0.38780 (18) | 1.13863 (19) | 0.70281 (11) | 0.0385 (5) | |
| C4 | 0.2975 (2) | 1.1376 (2) | 0.74929 (13) | 0.0484 (6) | |
| H4 | 0.2963 | 1.1893 | 0.7909 | 0.058* | |
| C5 | 0.2074 (2) | 1.0602 (2) | 0.73515 (14) | 0.0524 (6) | |
| H5 | 0.1461 | 1.0615 | 0.7667 | 0.063* | |
| C6 | 0.2092 (2) | 0.9832 (2) | 0.67549 (14) | 0.0474 (6) | |
| H6 | 0.1492 | 0.9312 | 0.6666 | 0.057* | |
| C7 | 0.30020 (17) | 0.8935 (2) | 0.56588 (11) | 0.0353 (5) | |
| H7 | 0.2404 | 0.8392 | 0.5646 | 0.042* | |
| C8 | 0.35710 (16) | 0.77989 (18) | 0.45869 (11) | 0.0326 (5) | |
| H8 | 0.3701 | 0.8150 | 0.4089 | 0.039* | |
| C9 | 0.24757 (18) | 0.7099 (2) | 0.45507 (13) | 0.0416 (5) | |
| H9A | 0.2249 | 0.6809 | 0.5041 | 0.050* | |
| H9B | 0.1891 | 0.7606 | 0.4338 | 0.050* | |
| C10 | 0.27792 (19) | 0.6031 (2) | 0.40378 (13) | 0.0447 (6) | |
| H10A | 0.2262 | 0.5350 | 0.4095 | 0.054* | |
| H10B | 0.2782 | 0.6292 | 0.3518 | 0.054* | |
| C11 | 0.3933 (2) | 0.5656 (2) | 0.42889 (18) | 0.0623 (8) | |
| H11A | 0.4389 | 0.5443 | 0.3860 | 0.075* | |
| H11B | 0.3897 | 0.4947 | 0.4621 | 0.075* | |
| C12 | 0.4416 (2) | 0.6771 (2) | 0.46972 (16) | 0.0532 (7) | |
| H12A | 0.4514 | 0.6591 | 0.5225 | 0.064* | |
| H12B | 0.5127 | 0.7002 | 0.4485 | 0.064* | |
| C13 | 0.4917 (2) | 1.2773 (3) | 0.77932 (19) | 0.0682 (9) | |
| H13A | 0.4325 | 1.3360 | 0.7847 | 0.102* | |
| H13B | 0.5614 | 1.3201 | 0.7793 | 0.102* | |
| H13C | 0.4898 | 1.2198 | 0.8203 | 0.102* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cu1 | 0.0323 (2) | 0.0320 (2) | 0.0301 (2) | −0.00396 (14) | 0.00267 (14) | −0.00402 (15) |
| O1 | 0.0444 (9) | 0.0600 (11) | 0.0385 (9) | −0.0173 (8) | 0.0109 (7) | −0.0169 (8) |
| O2 | 0.0556 (10) | 0.0581 (11) | 0.0457 (10) | −0.0085 (8) | −0.0009 (8) | −0.0213 (9) |
| N1 | 0.0349 (10) | 0.0284 (9) | 0.0295 (9) | −0.0007 (7) | −0.0007 (7) | −0.0003 (7) |
| C1 | 0.0372 (12) | 0.0350 (12) | 0.0325 (11) | 0.0033 (9) | 0.0021 (9) | 0.0017 (9) |
| C2 | 0.0377 (12) | 0.0354 (11) | 0.0286 (10) | 0.0031 (9) | 0.0031 (9) | 0.0014 (9) |
| C3 | 0.0459 (13) | 0.0366 (11) | 0.0331 (11) | 0.0052 (10) | −0.0029 (10) | −0.0028 (9) |
| C4 | 0.0575 (15) | 0.0490 (14) | 0.0387 (13) | 0.0116 (12) | 0.0063 (11) | −0.0088 (11) |
| C5 | 0.0502 (15) | 0.0618 (16) | 0.0452 (14) | 0.0093 (13) | 0.0164 (11) | −0.0045 (12) |
| C6 | 0.0403 (14) | 0.0551 (15) | 0.0469 (14) | −0.0010 (11) | 0.0074 (11) | 0.0003 (11) |
| C7 | 0.0326 (11) | 0.0360 (12) | 0.0372 (12) | −0.0038 (9) | −0.0007 (9) | 0.0031 (9) |
| C8 | 0.0348 (11) | 0.0288 (10) | 0.0342 (11) | −0.0037 (8) | −0.0020 (9) | −0.0001 (9) |
| C9 | 0.0411 (12) | 0.0405 (13) | 0.0430 (13) | −0.0061 (10) | −0.0021 (10) | −0.0025 (10) |
| C10 | 0.0533 (15) | 0.0346 (12) | 0.0461 (13) | −0.0109 (10) | −0.0034 (11) | −0.0016 (10) |
| C11 | 0.0654 (18) | 0.0343 (13) | 0.087 (2) | 0.0071 (12) | −0.0115 (16) | −0.0115 (13) |
| C12 | 0.0479 (15) | 0.0426 (14) | 0.0691 (17) | 0.0101 (11) | −0.0195 (13) | −0.0094 (13) |
| C13 | 0.076 (2) | 0.071 (2) | 0.0575 (17) | 0.0026 (15) | −0.0138 (14) | −0.0303 (16) |
| Cu1—O1 | 1.8770 (16) | C7—H7 | 0.9300 |
| Cu1—O1i | 1.8770 (16) | C8—C12 | 1.520 (3) |
| Cu1—N1 | 2.0208 (17) | C8—C9 | 1.523 (3) |
| Cu1—N1i | 2.0208 (17) | C8—H8 | 0.9800 |
| O1—C2 | 1.301 (2) | C9—C10 | 1.518 (3) |
| O2—C3 | 1.369 (3) | C9—H9A | 0.9700 |
| O2—C13 | 1.410 (4) | C9—H9B | 0.9700 |
| N1—C7 | 1.284 (3) | C10—C11 | 1.517 (3) |
| N1—C8 | 1.478 (3) | C10—H10A | 0.9700 |
| C1—C2 | 1.403 (3) | C10—H10B | 0.9700 |
| C1—C6 | 1.416 (3) | C11—C12 | 1.523 (3) |
| C1—C7 | 1.435 (3) | C11—H11A | 0.9700 |
| C2—C3 | 1.427 (3) | C11—H11B | 0.9700 |
| C3—C4 | 1.369 (3) | C12—H12A | 0.9700 |
| C4—C5 | 1.395 (4) | C12—H12B | 0.9700 |
| C4—H4 | 0.9300 | C13—H13A | 0.9600 |
| C5—C6 | 1.352 (3) | C13—H13B | 0.9600 |
| C5—H5 | 0.9300 | C13—H13C | 0.9600 |
| C6—H6 | 0.9300 | ||
| O1—Cu1—O1i | 180.00 (4) | C12—C8—C9 | 102.97 (17) |
| O1—Cu1—N1 | 91.06 (7) | N1—C8—H8 | 107.0 |
| O1i—Cu1—N1 | 88.94 (7) | C12—C8—H8 | 107.0 |
| O1—Cu1—N1i | 88.94 (7) | C9—C8—H8 | 107.0 |
| O1i—Cu1—N1i | 91.06 (7) | C10—C9—C8 | 101.17 (17) |
| N1—Cu1—N1i | 180.0 | C10—C9—H9A | 111.5 |
| C2—O1—Cu1 | 128.71 (14) | C8—C9—H9A | 111.5 |
| C3—O2—C13 | 118.1 (2) | C10—C9—H9B | 111.5 |
| C7—N1—C8 | 118.47 (18) | C8—C9—H9B | 111.5 |
| C7—N1—Cu1 | 122.43 (14) | H9A—C9—H9B | 109.4 |
| C8—N1—Cu1 | 119.04 (12) | C11—C10—C9 | 104.20 (19) |
| C2—C1—C6 | 120.1 (2) | C11—C10—H10A | 110.9 |
| C2—C1—C7 | 121.69 (19) | C9—C10—H10A | 110.9 |
| C6—C1—C7 | 118.1 (2) | C11—C10—H10B | 110.9 |
| O1—C2—C1 | 123.93 (19) | C9—C10—H10B | 110.9 |
| O1—C2—C3 | 118.5 (2) | H10A—C10—H10B | 108.9 |
| C1—C2—C3 | 117.56 (19) | C10—C11—C12 | 106.4 (2) |
| O2—C3—C4 | 125.3 (2) | C10—C11—H11A | 110.5 |
| O2—C3—C2 | 114.17 (19) | C12—C11—H11A | 110.5 |
| C4—C3—C2 | 120.6 (2) | C10—C11—H11B | 110.5 |
| C3—C4—C5 | 121.0 (2) | C12—C11—H11B | 110.5 |
| C3—C4—H4 | 119.5 | H11A—C11—H11B | 108.7 |
| C5—C4—H4 | 119.5 | C8—C12—C11 | 105.01 (18) |
| C6—C5—C4 | 119.9 (2) | C8—C12—H12A | 110.7 |
| C6—C5—H5 | 120.0 | C11—C12—H12A | 110.7 |
| C4—C5—H5 | 120.0 | C8—C12—H12B | 110.7 |
| C5—C6—C1 | 120.8 (2) | C11—C12—H12B | 110.7 |
| C5—C6—H6 | 119.6 | H12A—C12—H12B | 108.8 |
| C1—C6—H6 | 119.6 | O2—C13—H13A | 109.5 |
| N1—C7—C1 | 127.7 (2) | O2—C13—H13B | 109.5 |
| N1—C7—H7 | 116.1 | H13A—C13—H13B | 109.5 |
| C1—C7—H7 | 116.1 | O2—C13—H13C | 109.5 |
| N1—C8—C12 | 111.95 (17) | H13A—C13—H13C | 109.5 |
| N1—C8—C9 | 120.09 (17) | H13B—C13—H13C | 109.5 |
| Symmetry codes: (i) −x+1, −y+2, −z+1. |
Bruker (2000). SMART (Version 5.625), SAINT (Version 6.01), SHELXTL (Version 6.10) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA.
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Liu, H., Wang, H., Niu, D. & Lu, Z. (2004). Acta Cryst. E60, m1941–m1942.
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The interesting Cu(II) complexes with Schiff base ligands have been widely reported previously (Xu et al., 2005; Hebbachi & Benali-Cherif, 2005; Liu et al., 2004; Zhang, 2004; Wang, 2007; Usha et al., 2004). We report herein the title new copper(II) complex, (I), derived from the Schiff base ligand, 2-(cyclopentyliminomethyl)-6-methoxyphenol.
(I) is a mononuclear copper(II) complex (Fig. 1).