In the title mononuclear complex, [Cu(C
9H
9O
3)
2(H
2O)
2], the Cu
II ion, located on an inversion center, is hexacoordinated by four O atoms from two benzyloxyacetate ligands [Cu—O = 1.9420 (14) and 2.2922 (14) Å] and two water molecules [Cu—O = 2.0157 (15) Å] in a distorted octahedral geometry. In the crystal structure, intermolecular O—H

O hydrogen bonds link the molecules into layers parallel to the
bc plane.
Supporting information
CCDC reference: 688838
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.034
- wR factor = 0.083
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C1 .. 5.01 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
The ligand, benzyloxyacetic acid was commercially available and used without
further purification. The title complex was prepared by the addition of
Cu(Ac)2.H2O (4.00 g, 20 mmol) to a hot aqueous solution of benzyloxyacetic
acid (1.66 g, 10 mmol); the pH was adjusted to 6 with 0.1M sodium
hydroxide. The solution was allowed to evaporate at room temperature. Blue
prismatic crystals were separated from the filtered solution after several
days.
C&H analysis. Calc. for C18H22CuO8: C 50.28, H 5.16%. Found: C 50.26, H
5.17%.
The C-bound H atoms were placed in calculated positions,
with C—H = 0.93 or 0.97 Å, and were refined in the
riding-model approximation,
with Uiso(H) = 1.2Ueq(C).
The H atoms of the water molecule were located
in a difference Fourier map and refined with
bond restrint O—H = 0.84 (2) Å
in the riding-model approximation, with
Uiso(H) = 1.5Ueq(O).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008).
Diaquabis(benzyloxyacetato)copper(II)
top
Crystal data top
[Cu(C9H9O3)2(H2O)2] | F(000) = 446 |
Mr = 429.91 | Dx = 1.536 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7991 reflections |
a = 11.8847 (4) Å | θ = 1.8–27.6° |
b = 7.1509 (2) Å | µ = 1.22 mm−1 |
c = 11.6564 (5) Å | T = 296 K |
β = 110.283 (3)° | Prism, blue |
V = 929.21 (6) Å3 | 0.32 × 0.24 × 0.18 mm |
Z = 2 | |
Data collection top
Bruker P4 diffractometer | 2144 independent reflections |
Radiation source: fine-focus sealed tube | 1606 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 10.000 pixels mm-1 | θmax = 27.6°, θmin = 1.8° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −9→8 |
Tmin = 0.711, Tmax = 0.803 | l = −15→10 |
7991 measured reflections | |
Refinement top
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0429P)2] where P = (Fo2 + 2Fc2)/3 |
2144 reflections | (Δ/σ)max < 0.001 |
130 parameters | Δρmax = 0.40 e Å−3 |
3 restraints | Δρmin = −0.57 e Å−3 |
Crystal data top
[Cu(C9H9O3)2(H2O)2] | V = 929.21 (6) Å3 |
Mr = 429.91 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.8847 (4) Å | µ = 1.22 mm−1 |
b = 7.1509 (2) Å | T = 296 K |
c = 11.6564 (5) Å | 0.32 × 0.24 × 0.18 mm |
β = 110.283 (3)° | |
Data collection top
Bruker P4 diffractometer | 2144 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1606 reflections with I > 2σ(I) |
Tmin = 0.711, Tmax = 0.803 | Rint = 0.035 |
7991 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.034 | 3 restraints |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.40 e Å−3 |
2144 reflections | Δρmin = −0.57 e Å−3 |
130 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.5000 | 0.0000 | 0.5000 | 0.02860 (13) | |
O1 | 0.47417 (14) | 0.2249 (2) | 0.58090 (13) | 0.0345 (4) | |
O2 | 0.53762 (17) | 0.4957 (2) | 0.67150 (14) | 0.0417 (4) | |
O3 | 0.66880 (13) | 0.1742 (2) | 0.52517 (14) | 0.0407 (4) | |
O1W | 0.42562 (15) | 0.1187 (2) | 0.33393 (14) | 0.0374 (4) | |
C1 | 0.5503 (2) | 0.3554 (3) | 0.61482 (17) | 0.0325 (5) | |
C2 | 0.6644 (2) | 0.3444 (3) | 0.5852 (2) | 0.0376 (5) | |
C3 | 0.7506 (2) | 0.1723 (4) | 0.4603 (2) | 0.0442 (6) | |
C4 | 0.8798 (2) | 0.1745 (3) | 0.54208 (19) | 0.0341 (5) | |
C5 | 0.9166 (2) | 0.0908 (4) | 0.6556 (2) | 0.0427 (6) | |
C6 | 1.0355 (3) | 0.0908 (4) | 0.7283 (2) | 0.0510 (7) | |
C7 | 1.1196 (2) | 0.1751 (4) | 0.6891 (2) | 0.0513 (7) | |
C8 | 1.0844 (2) | 0.2568 (4) | 0.5758 (3) | 0.0507 (7) | |
C9 | 0.9650 (2) | 0.2583 (4) | 0.5025 (2) | 0.0430 (6) | |
H1W1 | 0.425 (2) | 0.2360 (13) | 0.335 (2) | 0.056* | |
H1W2 | 0.457 (2) | 0.075 (3) | 0.286 (2) | 0.056* | |
H2A | 0.6675 | 0.4486 | 0.5331 | 0.045* | |
H2B | 0.7333 | 0.3530 | 0.6601 | 0.045* | |
H3A | 0.7352 | 0.2803 | 0.4067 | 0.053* | |
H3B | 0.7361 | 0.0612 | 0.4094 | 0.053* | |
H5A | 0.8604 | 0.0339 | 0.6833 | 0.051* | |
H6A | 1.0593 | 0.0333 | 0.8045 | 0.061* | |
H7A | 1.1998 | 0.1768 | 0.7392 | 0.062* | |
H8A | 1.1414 | 0.3115 | 0.5482 | 0.061* | |
H9A | 0.9416 | 0.3157 | 0.4262 | 0.052* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0348 (2) | 0.0229 (2) | 0.03073 (19) | −0.00185 (16) | 0.01464 (16) | −0.00319 (15) |
O1 | 0.0435 (9) | 0.0261 (8) | 0.0393 (8) | −0.0028 (7) | 0.0212 (7) | −0.0052 (7) |
O2 | 0.0643 (11) | 0.0267 (9) | 0.0400 (8) | −0.0002 (8) | 0.0254 (8) | −0.0066 (7) |
O1W | 0.0465 (10) | 0.0316 (9) | 0.0357 (8) | 0.0020 (8) | 0.0160 (7) | 0.0004 (7) |
C1 | 0.0444 (13) | 0.0287 (12) | 0.0245 (9) | 0.0028 (10) | 0.0122 (10) | 0.0021 (9) |
C2 | 0.0400 (13) | 0.0300 (13) | 0.0423 (12) | −0.0057 (10) | 0.0136 (11) | −0.0086 (10) |
O3 | 0.0369 (9) | 0.0375 (9) | 0.0537 (9) | −0.0061 (7) | 0.0234 (8) | −0.0147 (8) |
C3 | 0.0414 (14) | 0.0559 (17) | 0.0389 (12) | −0.0013 (12) | 0.0188 (11) | −0.0086 (11) |
C4 | 0.0382 (12) | 0.0335 (12) | 0.0347 (11) | 0.0017 (10) | 0.0178 (10) | −0.0028 (9) |
C5 | 0.0493 (16) | 0.0419 (14) | 0.0427 (12) | 0.0061 (12) | 0.0233 (12) | 0.0054 (11) |
C6 | 0.0590 (18) | 0.0537 (17) | 0.0393 (13) | 0.0205 (14) | 0.0158 (13) | 0.0053 (12) |
C7 | 0.0400 (14) | 0.0482 (17) | 0.0584 (15) | 0.0070 (13) | 0.0077 (13) | −0.0118 (13) |
C8 | 0.0413 (15) | 0.0456 (16) | 0.0726 (18) | −0.0036 (12) | 0.0289 (14) | −0.0005 (14) |
C9 | 0.0453 (14) | 0.0432 (15) | 0.0459 (13) | 0.0038 (11) | 0.0225 (12) | 0.0055 (11) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.9420 (14) | C3—C4 | 1.500 (3) |
Cu1—O3 | 2.2922 (14) | C3—H3A | 0.9700 |
Cu1—O1W | 2.0157 (15) | C3—H3B | 0.9700 |
O1—C1 | 1.264 (3) | C4—C5 | 1.379 (3) |
O2—C1 | 1.239 (2) | C4—C9 | 1.386 (3) |
Cu1—O1i | 1.9420 (14) | C5—C6 | 1.372 (4) |
Cu1—O3i | 2.2922 (14) | C5—H5A | 0.9300 |
Cu1—O1Wi | 2.0157 (15) | C6—C7 | 1.374 (4) |
O3—C3 | 1.424 (2) | C6—H6A | 0.9300 |
O1W—H1W1 | 0.839 (9) | C7—C8 | 1.370 (4) |
O1W—H1W2 | 0.83 (2) | C7—H7A | 0.9300 |
C1—C2 | 1.512 (3) | C8—C9 | 1.380 (4) |
C2—O3 | 1.414 (2) | C8—H8A | 0.9300 |
C2—H2A | 0.9700 | C9—H9A | 0.9300 |
C2—H2B | 0.9700 | | |
| | | |
O1i—Cu1—O1 | 180.00 (7) | C1—C2—H2B | 109.6 |
O1i—Cu1—O3 | 103.51 (6) | C2—O3—C3 | 114.88 (17) |
O1—Cu1—O3 | 76.49 (6) | C2—O3—Cu1 | 110.48 (12) |
O1i—Cu1—O1W | 88.45 (6) | C3—O3—Cu1 | 130.94 (13) |
O1—Cu1—O1W | 91.55 (6) | C4—C3—H3A | 108.9 |
O3—Cu1—O3i | 180.0 | C4—C3—H3B | 108.9 |
O1W—Cu1—O3 | 88.11 (6) | C4—C5—H5A | 119.7 |
O1Wi—Cu1—O3 | 91.89 (6) | C4—C9—H9A | 119.9 |
O1W—Cu1—O1Wi | 180.0 | C5—C4—C9 | 118.8 (2) |
Cu1—O1W—H1W1 | 114.0 (18) | C5—C4—C3 | 121.3 (2) |
Cu1—O1W—H1W2 | 109.5 (18) | C5—C6—C7 | 120.4 (2) |
O1i—Cu1—O3i | 76.49 (6) | C5—C6—H6A | 119.8 |
O1—Cu1—O3i | 103.51 (6) | C6—C5—C4 | 120.6 (2) |
O1i—Cu1—O1Wi | 91.55 (6) | C6—C5—H5A | 119.7 |
O1—Cu1—O1Wi | 88.45 (6) | C6—C7—H7A | 120.2 |
O1—C1—C2 | 119.44 (18) | C7—C6—H6A | 119.8 |
O2—C1—O1 | 123.9 (2) | C7—C8—C9 | 120.3 (2) |
O2—C1—C2 | 116.6 (2) | C7—C8—H8A | 119.9 |
O3—C2—C1 | 110.35 (18) | C8—C7—C6 | 119.6 (2) |
O3—C2—H2A | 109.6 | C8—C7—H7A | 120.2 |
O3—C2—H2B | 109.6 | C8—C9—C4 | 120.3 (2) |
O3—C3—C4 | 113.51 (18) | C8—C9—H9A | 119.9 |
O3—C3—H3A | 108.9 | C9—C8—H8A | 119.9 |
O3—C3—H3B | 108.9 | C9—C4—C3 | 119.9 (2) |
O1W—Cu1—O3i | 91.89 (6) | H1W1—O1W—H1W2 | 113.6 (15) |
O1Wi—Cu1—O3i | 88.11 (6) | H2A—C2—H2B | 108.1 |
C1—O1—Cu1 | 123.14 (13) | H3A—C3—H3B | 107.7 |
C1—C2—H2A | 109.6 | | |
| | | |
Cu1—O1—C1—O2 | −176.53 (15) | O1W—Cu1—O3—C2 | 92.76 (14) |
Cu1—O1—C1—C2 | 3.9 (3) | O1Wi—Cu1—O3—C2 | −87.24 (14) |
Cu1—O3—C3—C4 | −134.22 (17) | O1W—Cu1—O3—C3 | −63.95 (19) |
O1i—Cu1—O3—C2 | −179.29 (13) | O1Wi—Cu1—O3—C3 | 116.05 (19) |
O1—Cu1—O3—C2 | 0.71 (13) | C1—C2—O3—C3 | 161.48 (18) |
O1i—Cu1—O3—C3 | 24.0 (2) | C1—C2—O3—Cu1 | 0.7 (2) |
O1—Cu1—O3—C3 | −156.0 (2) | C2—O3—C3—C4 | 69.9 (3) |
O1—C1—C2—O3 | −2.8 (3) | C3—C4—C5—C6 | 178.6 (2) |
O2—C1—C2—O3 | 177.60 (17) | C3—C4—C9—C8 | −178.3 (2) |
O3—Cu1—O1—C1 | −2.51 (15) | C4—C5—C6—C7 | 0.3 (4) |
O3i—Cu1—O1—C1 | 177.49 (15) | C5—C4—C9—C8 | 0.2 (3) |
O3—C3—C4—C5 | 31.9 (3) | C5—C6—C7—C8 | −1.2 (4) |
O3—C3—C4—C9 | −149.7 (2) | C6—C7—C8—C9 | 1.5 (4) |
O1W—Cu1—O1—C1 | −90.19 (16) | C7—C8—C9—C4 | −1.0 (4) |
O1Wi—Cu1—O1—C1 | 89.81 (16) | C9—C4—C5—C6 | 0.1 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O2ii | 0.84 (1) | 1.98 (1) | 2.796 (2) | 165 (2) |
O1W—H1W2···O2iii | 0.83 (2) | 1.96 (1) | 2.788 (2) | 173 (2) |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data |
Chemical formula | [Cu(C9H9O3)2(H2O)2] |
Mr | 429.91 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 11.8847 (4), 7.1509 (2), 11.6564 (5) |
β (°) | 110.283 (3) |
V (Å3) | 929.21 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.22 |
Crystal size (mm) | 0.32 × 0.24 × 0.18 |
|
Data collection |
Diffractometer | Bruker P4 diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.711, 0.803 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7991, 2144, 1606 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.653 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.082, 1.03 |
No. of reflections | 2144 |
No. of parameters | 130 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.40, −0.57 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O2i | 0.839 (9) | 1.978 (12) | 2.796 (2) | 165 (2) |
O1W—H1W2···O2ii | 0.83 (2) | 1.964 (10) | 2.788 (2) | 173 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2. |
Current interests in supramolecular chemistry are rapidly expanding for their intriguing architectures and potential applications (Eddaoudi et al., 2005). The organic aromatic carboxylate ligand, benzyloxyacetate, has various coordination modes and can link metal centres through carboxylate groups or/and benzyloxy group into different extended architectures. Therefore, benzyloxyacetate can be considered as a good candidate to construct various metal-organic complexes. Herein we report the crystal structure of the title mononuclear complex of benzyloxyacetate, [Cu(C9H9O3)2(H2O)2], (I).
As illustrated in Fig. 1, the CuII ion lies on an inversion center and displays an octahedral geometry defined by four carboxylate O atoms from two different benzyloxyacetate ligands and two water molecules. The Cu—O and Cu—Ow bond lengths are 1.942 (1), 2.292 (1) and 2.016 (2) Å, respectively. The characteristic C—O(carboxylate) bond lengths suggest electron localization of the carboxylate groups of the anionic ligands. In the crystal structure, intermolecular hydrogen bonds (Table 1) give rise to a supramolecular structure.