Acta Cryst. (2007). E63, m1853-m1854 [ doi:10.1107/S1600536807027717 ]
![[mu]](/logos/entities/mu_rmgif.gif)
3-1-(3-methoxy-2-oxidobenzylideneamino)-2-(2-oxidobenzamido)ethane]In the title compound, [CuK(C17H15N2O4)(CH3OH)]n, the CuII ion has a square-planar coordination geometry and is coordinated by two N and two O atoms. One phenoxo and the amide O atom also interact with the methanol-coordinated K+ ion along with the methoxy O atom of the trianion. Two bridging interactions to K+ give rise to a linear chain structure. The chains are further linked by hydrogen bonds involving the amido methanol O atoms into a two-dimensional network structure.
The compound was prepared according to the literature method (Kido et al., 2003), and recrystallization from methanol afforded violet, block-shaped crystals.
The H atoms bound to C atoms were placed in caculated positions with C—H = 0.93–0.77 Å and included in the refinement with Uiso(H) = 1.2Ueq(C). The H atom attached to the methanol O atom were found from E-map, and was fixed with O—H = 0.85 Å and refined isotropically.
Data collection: CrystalStructure (Rigaku/MSC, 2004); cell refinement: CrystalStructure; data reduction: CrystalStructure; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1998); software used to prepare material for publication: XP.
![[Figure 1]](./ng2273fig1thm.gif)
| Fig. 1. A view of complex (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. Symmetry code: i −x, 1 − y, −z; ii 1 − x, 1 − y, −z. |
![[Figure 2]](./ng2273fig2thm.gif)
| Fig. 2. The hydrogen-bonded layer structure. |
| [CuK(C17H15N2O4)(CH4O)] | Z = 2 |
| Mr = 445.99 | F000 = 458 |
| Triclinic, P1 | Dx = 1.596 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 8.851 (6) Å | Cell parameters from 4201 reflections |
| b = 9.139 (6) Å | θ = 3.0–27.5º |
| c = 12.458 (6) Å | µ = 1.43 mm−1 |
| α = 72.19 (2)º | T = 293 (2) K |
| β = 77.68 (3)º | Block, violet |
| γ = 78.69 (2)º | 0.2 × 0.2 × 0.18 mm |
| V = 928.0 (10) Å3 |
| Rigaku R-AXIS RAPID IP diffractometer | 4201 independent reflections |
| Radiation source: fine-focus sealed tube | 3241 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.045 |
| Detector resolution: 0.1 pixels mm-1 | θmax = 27.5º |
| T = 293(2) K | θmin = 3.0º |
| ω scans | h = −11→11 |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −11→11 |
| Tmin = 0.732, Tmax = 0.759 | l = −16→14 |
| 9074 measured reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
| wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.01P)2 + P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.02 | (Δ/σ)max < 0.001 |
| 4201 reflections | Δρmax = 0.55 e Å−3 |
| 246 parameters | Δρmin = −0.40 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| [CuK(C17H15N2O4)(CH4O)] | γ = 78.69 (2)º |
| Mr = 445.99 | V = 928.0 (10) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 8.851 (6) Å | Mo Kα |
| b = 9.139 (6) Å | µ = 1.43 mm−1 |
| c = 12.458 (6) Å | T = 293 (2) K |
| α = 72.19 (2)º | 0.2 × 0.2 × 0.18 mm |
| β = 77.68 (3)º |
| Rigaku R-AXIS RAPID IP diffractometer | 4201 independent reflections |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3241 reflections with I > 2σ(I) |
| Tmin = 0.732, Tmax = 0.759 | Rint = 0.045 |
| 9074 measured reflections |
| R[F2 > 2σ(F2)] = 0.042 | 246 parameters |
| wR(F2) = 0.091 | H-atom parameters constrained |
| S = 1.02 | Δρmax = 0.55 e Å−3 |
| 4201 reflections | Δρmin = −0.40 e Å−3 |
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 | 0.27702 (4) | 0.27166 (4) | 0.12226 (3) | 0.03185 (11) | |
| K1 | 0.03569 (8) | 0.65451 (7) | 0.05460 (6) | 0.03864 (17) | |
| O1 | 0.2426 (2) | 0.4267 (2) | −0.01471 (17) | 0.0358 (5) | |
| O2 | 0.0917 (2) | 0.3708 (2) | 0.20129 (17) | 0.0358 (5) | |
| N2 | 0.3005 (3) | 0.0990 (3) | 0.2574 (2) | 0.0325 (5) | |
| N1 | 0.4802 (3) | 0.1843 (3) | 0.0599 (2) | 0.0344 (6) | |
| C16 | 0.3546 (3) | 0.4689 (3) | −0.1033 (2) | 0.0311 (6) | |
| C11 | 0.5110 (3) | 0.3922 (3) | −0.1150 (3) | 0.0324 (6) | |
| O3 | 0.7203 (2) | 0.2010 (3) | −0.0501 (2) | 0.0442 (5) | |
| C1 | 0.0455 (3) | 0.3377 (3) | 0.3110 (3) | 0.0314 (6) | |
| C2 | −0.0732 (4) | 0.4438 (3) | 0.3569 (3) | 0.0350 (7) | |
| C7 | 0.2269 (4) | 0.0894 (3) | 0.3583 (3) | 0.0359 (7) | |
| H7A | 0.2556 | 0.0012 | 0.4153 | 0.043* | |
| C12 | 0.6138 (4) | 0.4529 (4) | −0.2151 (3) | 0.0414 (7) | |
| H12A | 0.7163 | 0.4038 | −0.2241 | 0.050* | |
| C8 | 0.4203 (4) | −0.0246 (3) | 0.2303 (3) | 0.0413 (7) | |
| H8A | 0.3758 | −0.0905 | 0.2010 | 0.050* | |
| H8B | 0.4613 | −0.0879 | 0.2987 | 0.050* | |
| C10 | 0.5754 (3) | 0.2510 (3) | −0.0307 (3) | 0.0328 (6) | |
| C6 | 0.1032 (3) | 0.2026 (3) | 0.3925 (3) | 0.0336 (6) | |
| C4 | −0.0790 (5) | 0.2770 (4) | 0.5471 (3) | 0.0513 (9) | |
| H4A | −0.1221 | 0.2557 | 0.6243 | 0.062* | |
| C15 | 0.3135 (4) | 0.6004 (4) | −0.1913 (3) | 0.0394 (7) | |
| H15A | 0.2120 | 0.6524 | −0.1840 | 0.047* | |
| C13 | 0.5699 (4) | 0.5814 (4) | −0.3001 (3) | 0.0477 (8) | |
| H13A | 0.6415 | 0.6179 | −0.3650 | 0.057* | |
| C9 | 0.5501 (4) | 0.0481 (4) | 0.1414 (3) | 0.0411 (7) | |
| H9A | 0.6202 | 0.0791 | 0.1780 | 0.049* | |
| H9B | 0.6098 | −0.0264 | 0.1017 | 0.049* | |
| C5 | 0.0393 (4) | 0.1755 (4) | 0.5088 (3) | 0.0438 (8) | |
| H5A | 0.0784 | 0.0865 | 0.5608 | 0.053* | |
| C3 | −0.1347 (4) | 0.4125 (4) | 0.4699 (3) | 0.0489 (8) | |
| H3A | −0.2148 | 0.4823 | 0.4958 | 0.059* | |
| C14 | 0.4183 (4) | 0.6552 (4) | −0.2879 (3) | 0.0445 (8) | |
| H14A | 0.3868 | 0.7421 | −0.3449 | 0.053* | |
| C17 | −0.2533 (4) | 0.6761 (4) | 0.3077 (3) | 0.0544 (9) | |
| H17A | −0.3396 | 0.6178 | 0.3350 | 0.082* | |
| H17B | −0.2751 | 0.7612 | 0.2427 | 0.082* | |
| H17C | −0.2377 | 0.7154 | 0.3672 | 0.082* | |
| O4 | −0.1159 (3) | 0.5782 (2) | 0.27564 (19) | 0.0434 (5) | |
| O5 | −0.1113 (3) | 0.9268 (3) | −0.06939 (19) | 0.0465 (6) | |
| C18 | 0.0008 (4) | 0.9855 (4) | −0.1635 (3) | 0.0485 (8) | |
| H18C | −0.0447 | 1.0816 | −0.2103 | 0.073* | |
| H18D | 0.0358 | 0.9119 | −0.2076 | 0.073* | |
| H18A | 0.0880 | 1.0031 | −0.1369 | 0.073* | |
| H5 | −0.1666 | 0.9996 | −0.0431 | 0.051 (10)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cu1 | 0.02267 (18) | 0.0323 (2) | 0.0352 (2) | 0.00534 (14) | −0.00369 (14) | −0.00796 (15) |
| K1 | 0.0325 (4) | 0.0315 (3) | 0.0475 (4) | 0.0003 (3) | −0.0073 (3) | −0.0071 (3) |
| O1 | 0.0230 (10) | 0.0383 (11) | 0.0373 (11) | 0.0031 (9) | −0.0011 (8) | −0.0051 (9) |
| O2 | 0.0295 (11) | 0.0350 (11) | 0.0335 (11) | 0.0051 (9) | 0.0009 (9) | −0.0060 (9) |
| N2 | 0.0260 (13) | 0.0281 (12) | 0.0404 (14) | 0.0042 (10) | −0.0064 (11) | −0.0094 (10) |
| N1 | 0.0241 (12) | 0.0313 (13) | 0.0436 (15) | 0.0057 (10) | −0.0048 (11) | −0.0109 (11) |
| C16 | 0.0279 (15) | 0.0329 (15) | 0.0333 (15) | −0.0044 (12) | 0.0013 (12) | −0.0145 (12) |
| C11 | 0.0268 (15) | 0.0351 (15) | 0.0390 (16) | −0.0021 (12) | −0.0017 (12) | −0.0196 (13) |
| O3 | 0.0213 (11) | 0.0412 (13) | 0.0683 (15) | 0.0018 (9) | 0.0018 (10) | −0.0223 (11) |
| C1 | 0.0239 (14) | 0.0300 (14) | 0.0384 (16) | −0.0044 (11) | −0.0005 (12) | −0.0094 (12) |
| C2 | 0.0331 (16) | 0.0312 (15) | 0.0394 (17) | −0.0031 (13) | −0.0032 (13) | −0.0105 (13) |
| C7 | 0.0370 (17) | 0.0283 (15) | 0.0382 (17) | −0.0015 (13) | −0.0096 (13) | −0.0029 (12) |
| C12 | 0.0313 (17) | 0.0494 (19) | 0.0463 (19) | −0.0108 (14) | 0.0043 (14) | −0.0213 (15) |
| C8 | 0.0355 (17) | 0.0314 (16) | 0.053 (2) | 0.0070 (13) | −0.0089 (15) | −0.0121 (14) |
| C10 | 0.0244 (14) | 0.0320 (15) | 0.0464 (18) | 0.0024 (12) | −0.0046 (13) | −0.0218 (13) |
| C6 | 0.0314 (16) | 0.0311 (15) | 0.0365 (16) | −0.0056 (12) | −0.0026 (12) | −0.0082 (12) |
| C4 | 0.060 (2) | 0.053 (2) | 0.0355 (18) | −0.0069 (18) | 0.0074 (16) | −0.0154 (16) |
| C15 | 0.0357 (17) | 0.0386 (17) | 0.0408 (17) | 0.0005 (14) | −0.0030 (14) | −0.0121 (14) |
| C13 | 0.048 (2) | 0.053 (2) | 0.0407 (19) | −0.0169 (17) | 0.0088 (15) | −0.0162 (16) |
| C9 | 0.0300 (16) | 0.0368 (17) | 0.052 (2) | 0.0101 (13) | −0.0085 (14) | −0.0142 (15) |
| C5 | 0.050 (2) | 0.0398 (18) | 0.0374 (17) | −0.0071 (15) | −0.0047 (15) | −0.0060 (14) |
| C3 | 0.050 (2) | 0.047 (2) | 0.047 (2) | −0.0006 (16) | 0.0064 (16) | −0.0215 (16) |
| C14 | 0.054 (2) | 0.0429 (18) | 0.0345 (17) | −0.0118 (16) | −0.0017 (15) | −0.0080 (14) |
| C17 | 0.041 (2) | 0.047 (2) | 0.069 (2) | 0.0122 (16) | −0.0041 (18) | −0.0220 (18) |
| O4 | 0.0370 (13) | 0.0357 (12) | 0.0485 (13) | 0.0106 (10) | −0.0024 (10) | −0.0113 (10) |
| O5 | 0.0439 (14) | 0.0376 (13) | 0.0495 (14) | 0.0036 (11) | −0.0018 (11) | −0.0096 (11) |
| C18 | 0.0379 (19) | 0.048 (2) | 0.053 (2) | −0.0013 (16) | −0.0014 (16) | −0.0107 (16) |
| Cu1—O1 | 1.893 (2) | C7—H7A | 0.9300 |
| Cu1—N1 | 1.922 (3) | C12—C13 | 1.374 (5) |
| Cu1—O2 | 1.937 (2) | C12—H12A | 0.9300 |
| Cu1—N2 | 1.940 (3) | C8—C9 | 1.515 (5) |
| K1—O2 | 2.701 (3) | C8—H8A | 0.9700 |
| K1—O1 | 2.714 (2) | C8—H8B | 0.9700 |
| K1—O3i | 2.726 (3) | C6—C5 | 1.402 (4) |
| K1—O4 | 2.736 (3) | C4—C5 | 1.364 (5) |
| K1—O5 | 2.740 (3) | C4—C3 | 1.392 (5) |
| K1—O1ii | 2.886 (3) | C4—H4A | 0.9300 |
| O1—C16 | 1.331 (3) | C15—C14 | 1.377 (5) |
| O1—K1ii | 2.886 (3) | C15—H15A | 0.9300 |
| O2—C1 | 1.298 (4) | C13—C14 | 1.378 (5) |
| N2—C7 | 1.272 (4) | C13—H13A | 0.9300 |
| N2—C8 | 1.457 (4) | C9—H9A | 0.9700 |
| N1—C10 | 1.315 (4) | C9—H9B | 0.9700 |
| N1—C9 | 1.469 (4) | C5—H5A | 0.9300 |
| C16—C15 | 1.403 (4) | C3—H3A | 0.9300 |
| C16—C11 | 1.423 (4) | C14—H14A | 0.9300 |
| C11—C12 | 1.407 (4) | C17—O4 | 1.422 (4) |
| C11—C10 | 1.494 (4) | C17—H17A | 0.9600 |
| O3—C10 | 1.272 (3) | C17—H17B | 0.9600 |
| O3—K1i | 2.726 (3) | C17—H17C | 0.9600 |
| C1—C6 | 1.422 (4) | O5—C18 | 1.406 (4) |
| C1—C2 | 1.433 (4) | O5—H5 | 0.8521 |
| C2—C3 | 1.358 (5) | C18—H18C | 0.9600 |
| C2—O4 | 1.377 (4) | C18—H18D | 0.9600 |
| C7—C6 | 1.441 (4) | C18—H18A | 0.9600 |
| O1—Cu1—N1 | 95.19 (10) | N2—C8—C9 | 108.7 (3) |
| O1—Cu1—O2 | 88.75 (9) | N2—C8—H8A | 110.0 |
| N1—Cu1—O2 | 169.99 (10) | C9—C8—H8A | 110.0 |
| O1—Cu1—N2 | 173.78 (10) | N2—C8—H8B | 110.0 |
| N1—Cu1—N2 | 85.22 (11) | C9—C8—H8B | 110.0 |
| O2—Cu1—N2 | 91.86 (10) | H8A—C8—H8B | 108.3 |
| O2—K1—O1 | 59.32 (7) | O3—C10—N1 | 123.1 (3) |
| O2—K1—O3i | 104.21 (8) | O3—C10—C11 | 118.2 (3) |
| O1—K1—O3i | 89.14 (8) | N1—C10—C11 | 118.7 (2) |
| O2—K1—O4 | 57.36 (7) | C5—C6—C1 | 120.4 (3) |
| O1—K1—O4 | 116.65 (7) | C5—C6—C7 | 118.2 (3) |
| O3i—K1—O4 | 107.21 (8) | C1—C6—C7 | 121.4 (3) |
| O2—K1—O5 | 162.88 (7) | C5—C4—C3 | 119.4 (3) |
| O1—K1—O5 | 130.64 (8) | C5—C4—H4A | 120.3 |
| O3i—K1—O5 | 90.63 (9) | C3—C4—H4A | 120.3 |
| O4—K1—O5 | 110.44 (8) | C14—C15—C16 | 122.3 (3) |
| O2—K1—O1ii | 90.43 (7) | C14—C15—H15A | 118.8 |
| O1—K1—O1ii | 97.52 (7) | C16—C15—H15A | 118.8 |
| O3i—K1—O1ii | 165.31 (7) | C12—C13—C14 | 119.0 (3) |
| O4—K1—O1ii | 81.53 (8) | C12—C13—H13A | 120.5 |
| O5—K1—O1ii | 75.08 (8) | C14—C13—H13A | 120.5 |
| C16—O1—Cu1 | 124.07 (18) | N1—C9—C8 | 108.6 (2) |
| C16—O1—K1 | 117.80 (17) | N1—C9—H9A | 110.0 |
| Cu1—O1—K1 | 104.65 (9) | C8—C9—H9A | 110.0 |
| C16—O1—K1ii | 118.66 (17) | N1—C9—H9B | 110.0 |
| Cu1—O1—K1ii | 100.64 (9) | C8—C9—H9B | 110.0 |
| K1—O1—K1ii | 82.48 (7) | H9A—C9—H9B | 108.4 |
| C1—O2—Cu1 | 126.37 (18) | C4—C5—C6 | 121.4 (3) |
| C1—O2—K1 | 124.59 (17) | C4—C5—H5A | 119.3 |
| Cu1—O2—K1 | 103.83 (9) | C6—C5—H5A | 119.3 |
| C7—N2—C8 | 122.0 (3) | C2—C3—C4 | 120.7 (3) |
| C7—N2—Cu1 | 127.1 (2) | C2—C3—H3A | 119.7 |
| C8—N2—Cu1 | 110.9 (2) | C4—C3—H3A | 119.7 |
| C10—N1—C9 | 116.5 (2) | C15—C14—C13 | 120.0 (3) |
| C10—N1—Cu1 | 127.7 (2) | C15—C14—H14A | 120.0 |
| C9—N1—Cu1 | 113.3 (2) | C13—C14—H14A | 120.0 |
| O1—C16—C15 | 116.7 (3) | O4—C17—H17A | 109.5 |
| O1—C16—C11 | 125.2 (3) | O4—C17—H17B | 109.5 |
| C15—C16—C11 | 118.1 (3) | H17A—C17—H17B | 109.5 |
| C12—C11—C16 | 117.5 (3) | O4—C17—H17C | 109.5 |
| C12—C11—C10 | 117.0 (3) | H17A—C17—H17C | 109.5 |
| C16—C11—C10 | 125.6 (3) | H17B—C17—H17C | 109.5 |
| C10—O3—K1i | 127.29 (18) | C2—O4—C17 | 117.3 (3) |
| O2—C1—C6 | 125.4 (3) | C2—O4—K1 | 123.72 (17) |
| O2—C1—C2 | 118.9 (3) | C17—O4—K1 | 118.8 (2) |
| C6—C1—C2 | 115.7 (3) | C18—O5—K1 | 105.91 (19) |
| C3—C2—O4 | 124.5 (3) | C18—O5—H5 | 110.9 |
| C3—C2—C1 | 122.2 (3) | K1—O5—H5 | 126.3 |
| O4—C2—C1 | 113.2 (3) | O5—C18—H18C | 109.5 |
| N2—C7—C6 | 126.0 (3) | O5—C18—H18D | 109.5 |
| N2—C7—H7A | 117.0 | H18C—C18—H18D | 109.5 |
| C6—C7—H7A | 117.0 | O5—C18—H18A | 109.5 |
| C13—C12—C11 | 123.1 (3) | H18C—C18—H18A | 109.5 |
| C13—C12—H12A | 118.4 | H18D—C18—H18A | 109.5 |
| C11—C12—H12A | 118.4 | ||
| N1—Cu1—O1—C16 | −15.7 (2) | K1—O2—C1—C6 | −164.0 (2) |
| O2—Cu1—O1—C16 | 155.1 (2) | Cu1—O2—C1—C2 | 166.0 (2) |
| K1ii—Cu1—O1—C16 | −135.7 (2) | K1—O2—C1—C2 | 15.8 (4) |
| N1—Cu1—O1—K1 | −155.04 (10) | O2—C1—C2—C3 | 175.7 (3) |
| O2—Cu1—O1—K1 | 15.73 (9) | C6—C1—C2—C3 | −4.5 (4) |
| N1—Cu1—O1—K1ii | 120.04 (10) | O2—C1—C2—O4 | −4.8 (4) |
| O2—Cu1—O1—K1ii | −69.19 (9) | C6—C1—C2—O4 | 175.1 (3) |
| O2—K1—O1—C16 | −155.5 (2) | C8—N2—C7—C6 | −177.6 (3) |
| O3i—K1—O1—C16 | −48.4 (2) | Cu1—N2—C7—C6 | 3.8 (5) |
| O4—K1—O1—C16 | −157.23 (18) | C16—C11—C12—C13 | 0.2 (5) |
| O5—K1—O1—C16 | 41.7 (2) | C10—C11—C12—C13 | 179.5 (3) |
| O1ii—K1—O1—C16 | 118.5 (2) | C7—N2—C8—C9 | −142.6 (3) |
| O3i—K1—O1—Cu1 | 94.05 (10) | Cu1—N2—C8—C9 | 36.3 (3) |
| O4—K1—O1—Cu1 | −14.83 (12) | K1i—O3—C10—N1 | −114.3 (3) |
| O5—K1—O1—Cu1 | −175.86 (8) | K1i—O3—C10—C11 | 65.8 (3) |
| O1ii—K1—O1—Cu1 | −99.09 (10) | C9—N1—C10—O3 | 1.4 (4) |
| O2—K1—O1—K1ii | 86.02 (8) | Cu1—N1—C10—O3 | 162.2 (2) |
| O3i—K1—O1—K1ii | −166.86 (7) | C9—N1—C10—C11 | −178.6 (2) |
| O4—K1—O1—K1ii | 84.26 (8) | Cu1—N1—C10—C11 | −17.8 (4) |
| O5—K1—O1—K1ii | −76.77 (10) | C12—C11—C10—O3 | 4.8 (4) |
| O1ii—K1—O1—K1ii | 0.0 | C16—C11—C10—O3 | −176.0 (3) |
| Cu1ii—K1—O1—K1ii | −29.86 (5) | C12—C11—C10—N1 | −175.2 (3) |
| O1—Cu1—O2—C1 | −170.9 (2) | C16—C11—C10—N1 | 4.1 (4) |
| N1—Cu1—O2—C1 | −57.5 (7) | O2—C1—C6—C5 | −177.1 (3) |
| N2—Cu1—O2—C1 | 15.3 (2) | C2—C1—C6—C5 | 3.1 (4) |
| K1ii—Cu1—O2—C1 | 141.3 (2) | O2—C1—C6—C7 | 2.2 (5) |
| O1—Cu1—O2—K1 | −15.75 (9) | C2—C1—C6—C7 | −177.6 (3) |
| N1—Cu1—O2—K1 | 97.6 (6) | N2—C7—C6—C5 | −177.6 (3) |
| N2—Cu1—O2—K1 | 170.44 (9) | N2—C7—C6—C1 | 3.1 (5) |
| O1—K1—O2—C1 | 168.4 (2) | O1—C16—C15—C14 | −179.5 (3) |
| O3i—K1—O2—C1 | 88.1 (2) | C11—C16—C15—C14 | 0.9 (5) |
| O4—K1—O2—C1 | −13.4 (2) | C11—C12—C13—C14 | 0.0 (5) |
| O5—K1—O2—C1 | −61.3 (3) | C10—N1—C9—C8 | −172.4 (3) |
| O1ii—K1—O2—C1 | −93.1 (2) | Cu1—N1—C9—C8 | 24.0 (3) |
| K1ii—K1—O2—C1 | −135.3 (2) | N2—C8—C9—N1 | −38.5 (3) |
| Cu1ii—K1—O2—C1 | −102.8 (2) | C3—C4—C5—C6 | −1.8 (6) |
| O1—K1—O2—Cu1 | 12.72 (7) | C1—C6—C5—C4 | −0.1 (5) |
| O3i—K1—O2—Cu1 | −67.59 (10) | C7—C6—C5—C4 | −179.4 (3) |
| O4—K1—O2—Cu1 | −169.14 (12) | O4—C2—C3—C4 | −176.7 (3) |
| O5—K1—O2—Cu1 | 143.0 (2) | C1—C2—C3—C4 | 2.8 (5) |
| O1ii—K1—O2—Cu1 | 111.21 (10) | C5—C4—C3—C2 | 0.5 (6) |
| N1—Cu1—N2—C7 | 159.9 (3) | C16—C15—C14—C13 | −0.7 (5) |
| O2—Cu1—N2—C7 | −10.5 (3) | C12—C13—C14—C15 | 0.3 (5) |
| O2—Cu1—N2—C8 | 170.7 (2) | C3—C2—O4—C17 | −12.8 (5) |
| K1ii—Cu1—N2—C8 | 99.6 (2) | C1—C2—O4—C17 | 167.7 (3) |
| O1—Cu1—N1—C10 | 21.4 (3) | C3—C2—O4—K1 | 171.7 (3) |
| O2—Cu1—N1—C10 | −91.5 (6) | C1—C2—O4—K1 | −7.8 (3) |
| N2—Cu1—N1—C10 | −164.9 (3) | O2—K1—O4—C2 | 10.4 (2) |
| O1—Cu1—N1—C9 | −177.3 (2) | O1—K1—O4—C2 | 12.2 (2) |
| O2—Cu1—N1—C9 | 69.8 (6) | O3i—K1—O4—C2 | −85.7 (2) |
| N2—Cu1—N1—C9 | −3.5 (2) | O5—K1—O4—C2 | 177.0 (2) |
| Cu1—O1—C16—C15 | −171.1 (2) | O1ii—K1—O4—C2 | 106.4 (2) |
| K1—O1—C16—C15 | −36.5 (3) | O2—K1—O4—C17 | −165.0 (3) |
| K1ii—O1—C16—C15 | 60.3 (3) | O1—K1—O4—C17 | −163.2 (2) |
| Cu1—O1—C16—C11 | 8.5 (4) | O3i—K1—O4—C17 | 98.9 (2) |
| K1—O1—C16—C11 | 143.1 (2) | O5—K1—O4—C17 | 1.6 (2) |
| K1ii—O1—C16—C11 | −120.0 (3) | O1ii—K1—O4—C17 | −69.0 (2) |
| O1—C16—C11—C12 | 179.8 (3) | O2—K1—O5—C18 | −159.7 (2) |
| C15—C16—C11—C12 | −0.6 (4) | O1—K1—O5—C18 | −39.6 (2) |
| O1—C16—C11—C10 | 0.6 (4) | O3i—K1—O5—C18 | 49.8 (2) |
| C15—C16—C11—C10 | −179.8 (3) | O4—K1—O5—C18 | 158.47 (19) |
| Cu1—O2—C1—C6 | −13.8 (4) | O1ii—K1—O5—C18 | −126.7 (2) |
| Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O5—H5···O3iii | 0.85 | 1.90 | 2.703 (4) | 156 |
| Symmetry codes: (iii) x−1, y+1, z. |
| Cu1—O1 | 1.893 (2) | K1—O1 | 2.714 (2) |
| Cu1—N1 | 1.922 (3) | K1—O3i | 2.726 (3) |
| Cu1—O2 | 1.937 (2) | K1—O4 | 2.736 (3) |
| Cu1—N2 | 1.940 (3) | K1—O5 | 2.740 (3) |
| K1—O2 | 2.701 (3) | K1—O1ii | 2.886 (3) |
| O1—Cu1—N1 | 95.19 (10) | O2—K1—O5 | 162.88 (7) |
| O1—Cu1—O2 | 88.75 (9) | O1—K1—O5 | 130.64 (8) |
| N1—Cu1—O2 | 169.99 (10) | O3i—K1—O5 | 90.63 (9) |
| O1—Cu1—N2 | 173.78 (10) | O4—K1—O5 | 110.44 (8) |
| N1—Cu1—N2 | 85.22 (11) | O2—K1—O1ii | 90.43 (7) |
| O2—Cu1—N2 | 91.86 (10) | O1—K1—O1ii | 97.52 (7) |
| O2—K1—O1 | 59.32 (7) | O3i—K1—O1ii | 165.31 (7) |
| O2—K1—O3i | 104.21 (8) | O4—K1—O1ii | 81.53 (8) |
| O1—K1—O3i | 89.14 (8) | O5—K1—O1ii | 75.08 (8) |
| O2—K1—O4 | 57.36 (7) | Cu1—O1—K1ii | 100.64 (9) |
| O1—K1—O4 | 116.65 (7) | K1—O1—K1ii | 82.48 (7) |
| O3i—K1—O4 | 107.21 (8) | Cu1—O2—K1 | 103.83 (9) |
| Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O5—H5···O3iii | 0.85 | 1.90 | 2.703 (4) | 156 |
| Symmetry codes: (iii) x−1, y+1, z. |
This work was supported by the Natural Science Foundation of China (No. 20671055).
Hamamatsu, T., Yabe, K., Towatari, M., Osa, S., Matsumoto, N., Re, N., Pochaba, A., Mrozinski, J., Gallani, J.-L., Baria, A., Imperia, P., Paulsen, C. & Kappler, J.-P. (2007). Inorg. Chem. 46, 4458–4468.
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1-(2-hydroxybenzamido)-2-(2-hydroxy-3-methoxybenzylideneamino)ethane, abbreviated as H3L, is an excellent bridging ligand that can link two metal atoms via the phenolato and the amido oxgen atoms to form polynuclear complexes (Kido et al., 2000). A few cyclic heterometallic tetranuclear complexes have been synthesize and their structures have been characterized by diffraction analysis and magnetic studies (Hamamatsu et al., 2007; Kido et al., 2003; Osa et al., 2003). The syntheses requires K[CuL] as the starting reactant. This compound crystallizes from methanol as the title compound.
The structure consists of [CuL]− and [K(MeOH)]+ moieties connected by the phenolato and amido oxygen atoms (Fig. 1). The coordination geometry of potassium is an octahedron, and that of copper is a square plane. Two N atoms and two O atoms are linked to the copper atom. The coordination environment is similar to those found in other cyclic heterometallic tetranuclear complexes.
The phenolato oxygen and amido oxgen atoms are involving in bridging to form a ladder structure (Fig. 2). Adjacent ladders are further linked by hydrogen bonds (involving the amido group and the methanol molecule) (O···O 2.702 (4) Å) to form a two-dimensional, hydrogen-bonded network.