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metal-organic compounds
In the title centrosymmetric dinuclear complex, [Cu2(3-CPOA)2(C3H4N2)4]·2H2O (3-CPOA2− is the 3-carboxylatophenoxyacetate dianion, C9H6O5), each CuII ion is coordinated by three carboxyl O atoms, one ether O atom from two 3–CPOA2− groups and two N atoms from two imidazole co-ligands, displaying an elongated square-pyramidal coordination geometry with a based capped by one very long semicoordinate Cu—Ocarboxyl bond [2.8191 (15) Å]. The two CuII ions are bridged by 3–CPOA2− ligands, generating a macrocyclic ring motif, with a CuCu separation of 6.879 (3) Å. The dinuclear motifs are further linked into a two-dimensional supramolecular network via hydrogen-bonding interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029976/lh6310sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029976/lh6310Isup2.hkl |
CCDC reference: 258708
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.099
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Bis(µ-3-carboxylatophenoxyacetato)bis[(1H-imidazole)copper(II)]
dihydrate top
Crystal data top
[Cu2(C9H6O5)2(C3H4N2)4]·2H2O | F(000) = 844 |
Mr = 823.74 | Dx = 1.551 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 15849 reflections |
a = 9.997 (2) Å | θ = 3.1–27.4° |
b = 16.422 (3) Å | µ = 1.28 mm−1 |
c = 10.857 (2) Å | T = 293 K |
β = 98.20 (3)° | Prism, blue |
V = 1764.2 (6) Å3 | 0.35 × 0.26 × 0.19 mm |
Z = 2 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 3982 independent reflections |
Radiation source: fine-focus sealed tube | 3319 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 10 pixels mm-1 | θmax = 27.4°, θmin = 3.1° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −21→21 |
Tmin = 0.663, Tmax = 0.793 | l = −13→14 |
16077 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0558P)2 + 0.5757P] where P = (Fo2 + 2Fc2)/3 |
3982 reflections | (Δ/σ)max = 0.001 |
241 parameters | Δρmax = 0.48 e Å−3 |
3 restraints | Δρmin = −0.28 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.14180 (3) | 0.625677 (16) | 0.73660 (2) | 0.04230 (11) | |
N1 | 0.2031 (2) | 0.51828 (12) | 0.80959 (19) | 0.0506 (4) | |
N2 | 0.2494 (2) | 0.38832 (13) | 0.8197 (2) | 0.0621 (6) | |
N3 | 0.08196 (19) | 0.73278 (11) | 0.66421 (18) | 0.0468 (4) | |
N4 | 0.0060 (2) | 0.82315 (13) | 0.52347 (19) | 0.0580 (5) | |
O1 | 0.29451 (16) | 0.67706 (10) | 0.83965 (14) | 0.0506 (4) | |
O2 | 0.50898 (17) | 0.71365 (11) | 0.87529 (17) | 0.0615 (5) | |
O3 | 0.31831 (17) | 0.62502 (10) | 0.61070 (16) | 0.0541 (4) | |
O4 | 0.01582 (15) | 0.43002 (9) | 0.35865 (14) | 0.0464 (3) | |
O5 | 0.11393 (18) | 0.40470 (11) | 0.19206 (16) | 0.0574 (4) | |
O1W | 0.2490 (2) | 0.24494 (13) | 0.6957 (3) | 0.0853 (7) | |
C1 | 0.1796 (3) | 0.44715 (15) | 0.7545 (3) | 0.0562 (6) | |
C2 | 0.2928 (3) | 0.50325 (17) | 0.9156 (2) | 0.0605 (6) | |
C3 | 0.3218 (3) | 0.42300 (18) | 0.9233 (3) | 0.0660 (7) | |
C4 | 0.0061 (3) | 0.74458 (16) | 0.5558 (2) | 0.0562 (6) | |
C5 | 0.1319 (3) | 0.80922 (15) | 0.7008 (2) | 0.0552 (6) | |
C6 | 0.0843 (3) | 0.86452 (15) | 0.6139 (3) | 0.0582 (6) | |
C7 | 0.4088 (2) | 0.68862 (13) | 0.8054 (2) | 0.0472 (5) | |
C8 | 0.4278 (2) | 0.67252 (15) | 0.6708 (2) | 0.0510 (5) | |
C9 | 0.3300 (2) | 0.58693 (13) | 0.49955 (19) | 0.0417 (4) | |
C10 | 0.4383 (2) | 0.59762 (15) | 0.4350 (2) | 0.0500 (5) | |
C11 | 0.4397 (2) | 0.55467 (16) | 0.3251 (2) | 0.0559 (6) | |
C12 | 0.3365 (2) | 0.50259 (16) | 0.2802 (2) | 0.0498 (5) | |
C13 | 0.2271 (2) | 0.49280 (12) | 0.34492 (19) | 0.0392 (4) | |
C14 | 0.2242 (2) | 0.53554 (13) | 0.45458 (19) | 0.0398 (4) | |
C15 | 0.1119 (2) | 0.43824 (13) | 0.2944 (2) | 0.0419 (5) | |
H1W1 | 0.217 (3) | 0.1972 (11) | 0.703 (4) | 0.128* | |
H1W2 | 0.326 (2) | 0.240 (2) | 0.671 (4) | 0.128* | |
H1 | 0.1223 | 0.4391 | 0.6802 | 0.067* | |
H2 | 0.3280 | 0.5424 | 0.9731 | 0.073* | |
H3 | 0.3790 | 0.3967 | 0.9859 | 0.079* | |
H4 | −0.0409 | 0.7038 | 0.5083 | 0.067* | |
H5 | 0.1892 | 0.8205 | 0.7740 | 0.066* | |
H6 | 0.1020 | 0.9201 | 0.6158 | 0.070* | |
H8A | 0.4319 | 0.7238 | 0.6272 | 0.061* | |
H8B | 0.5122 | 0.6438 | 0.6685 | 0.061* | |
H10 | 0.5085 | 0.6328 | 0.4645 | 0.060* | |
H11 | 0.5121 | 0.5613 | 0.2809 | 0.067* | |
H12 | 0.3398 | 0.4740 | 0.2068 | 0.060* | |
H14 | 0.1511 | 0.5297 | 0.4981 | 0.048* | |
H16 | 0.2489 | 0.3376 | 0.8001 | 0.075* | |
H17 | −0.0369 | 0.8438 | 0.4564 | 0.070* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.04254 (16) | 0.04153 (16) | 0.04086 (16) | −0.00437 (10) | −0.00078 (11) | −0.00196 (10) |
N1 | 0.0484 (10) | 0.0496 (11) | 0.0527 (11) | −0.0017 (9) | 0.0034 (9) | 0.0033 (9) |
N2 | 0.0626 (13) | 0.0508 (12) | 0.0765 (16) | 0.0038 (10) | 0.0220 (12) | 0.0097 (10) |
N3 | 0.0489 (10) | 0.0445 (10) | 0.0441 (10) | −0.0027 (8) | −0.0032 (8) | −0.0009 (8) |
N4 | 0.0635 (12) | 0.0576 (12) | 0.0502 (11) | 0.0068 (10) | −0.0010 (10) | 0.0117 (10) |
O1 | 0.0507 (9) | 0.0520 (9) | 0.0456 (8) | −0.0051 (7) | −0.0054 (7) | −0.0048 (7) |
O2 | 0.0508 (9) | 0.0635 (11) | 0.0638 (11) | −0.0044 (8) | −0.0135 (8) | −0.0149 (9) |
O3 | 0.0462 (9) | 0.0656 (11) | 0.0505 (9) | −0.0195 (7) | 0.0075 (7) | −0.0191 (8) |
O4 | 0.0436 (8) | 0.0488 (8) | 0.0462 (8) | −0.0093 (7) | 0.0045 (7) | −0.0054 (7) |
O5 | 0.0610 (10) | 0.0626 (10) | 0.0482 (9) | −0.0052 (8) | 0.0062 (8) | −0.0184 (8) |
O1W | 0.0708 (13) | 0.0620 (12) | 0.124 (2) | −0.0040 (10) | 0.0160 (14) | −0.0084 (13) |
C1 | 0.0541 (13) | 0.0477 (13) | 0.0666 (16) | −0.0004 (11) | 0.0083 (12) | 0.0064 (11) |
C2 | 0.0693 (16) | 0.0610 (15) | 0.0501 (14) | 0.0043 (13) | 0.0043 (12) | 0.0060 (12) |
C3 | 0.0686 (17) | 0.0688 (18) | 0.0613 (16) | 0.0099 (14) | 0.0115 (14) | 0.0180 (14) |
C4 | 0.0602 (14) | 0.0547 (14) | 0.0489 (13) | −0.0042 (11) | −0.0083 (11) | −0.0006 (11) |
C5 | 0.0577 (14) | 0.0469 (13) | 0.0571 (14) | −0.0023 (11) | −0.0053 (11) | −0.0053 (11) |
C6 | 0.0650 (16) | 0.0427 (13) | 0.0653 (16) | −0.0012 (11) | 0.0037 (13) | 0.0033 (11) |
C7 | 0.0481 (12) | 0.0342 (10) | 0.0547 (13) | 0.0011 (9) | −0.0081 (10) | −0.0033 (9) |
C8 | 0.0438 (11) | 0.0496 (13) | 0.0570 (13) | −0.0111 (10) | −0.0021 (10) | −0.0070 (10) |
C9 | 0.0427 (11) | 0.0427 (11) | 0.0390 (10) | −0.0023 (9) | 0.0039 (9) | 0.0009 (9) |
C10 | 0.0429 (11) | 0.0550 (13) | 0.0515 (13) | −0.0113 (10) | 0.0052 (10) | 0.0027 (10) |
C11 | 0.0457 (12) | 0.0721 (16) | 0.0527 (13) | −0.0085 (12) | 0.0167 (11) | 0.0006 (12) |
C12 | 0.0501 (12) | 0.0581 (14) | 0.0425 (11) | 0.0019 (10) | 0.0105 (10) | −0.0008 (10) |
C13 | 0.0378 (10) | 0.0401 (10) | 0.0390 (10) | 0.0018 (8) | 0.0033 (8) | 0.0019 (8) |
C14 | 0.0389 (10) | 0.0436 (11) | 0.0369 (10) | −0.0044 (8) | 0.0058 (8) | 0.0002 (8) |
C15 | 0.0441 (11) | 0.0386 (10) | 0.0409 (11) | 0.0021 (9) | −0.0011 (9) | −0.0014 (9) |
Geometric parameters (Å, º) top
Cu1—N1 | 1.994 (2) | O1W—H1W2 | 0.858 (10) |
Cu1—N3 | 1.9837 (19) | C1—H1 | 0.9300 |
Cu1—O1 | 1.9513 (16) | C2—C3 | 1.350 (4) |
Cu1—O3 | 2.3814 (18) | C2—H2 | 0.9300 |
Cu1—O4i | 1.9810 (15) | C3—H3 | 0.9300 |
Cu1—O5i | 2.8191 (15) | C4—H4 | 0.9300 |
O1—C7 | 1.266 (3) | C5—C6 | 1.347 (4) |
O2—C7 | 1.238 (3) | C5—H5 | 0.9300 |
O4—C15 | 1.273 (3) | C6—H6 | 0.9300 |
O5—C15 | 1.243 (3) | C7—C8 | 1.523 (3) |
N1—C1 | 1.318 (3) | C8—H8A | 0.9700 |
N1—C2 | 1.377 (3) | C8—H8B | 0.9700 |
N2—C1 | 1.334 (3) | C9—C10 | 1.382 (3) |
N2—C3 | 1.372 (4) | C9—C14 | 1.386 (3) |
N2—H16 | 0.8600 | C10—C11 | 1.388 (3) |
N3—C4 | 1.321 (3) | C10—H10 | 0.9300 |
N3—C5 | 1.388 (3) | C11—C12 | 1.375 (3) |
N4—C4 | 1.337 (3) | C11—H11 | 0.9300 |
N4—C6 | 1.349 (3) | C12—C13 | 1.391 (3) |
N4—H17 | 0.8600 | C12—H12 | 0.9300 |
O3—C8 | 1.424 (3) | C13—C14 | 1.386 (3) |
O3—C9 | 1.379 (3) | C13—C15 | 1.500 (3) |
O4—Cu1i | 1.9810 (15) | C14—H14 | 0.9300 |
O1W—H1W1 | 0.856 (10) | ||
N1—Cu1—O3 | 90.76 (7) | C2—C3—N2 | 105.7 (3) |
N3—Cu1—N1 | 179.65 (8) | C2—C3—H3 | 127.1 |
N3—Cu1—O3 | 89.02 (7) | C3—N2—H16 | 126.0 |
O1—Cu1—N1 | 89.07 (8) | C3—C2—N1 | 109.6 (3) |
O1—Cu1—N3 | 90.62 (8) | C3—C2—H2 | 125.2 |
O1—Cu1—O3 | 75.39 (6) | C4—N3—Cu1 | 125.85 (17) |
O1—Cu1—O4i | 176.45 (7) | C4—N3—C5 | 105.1 (2) |
O4i—Cu1—N1 | 88.60 (8) | C4—N4—C6 | 108.5 (2) |
O4i—Cu1—N3 | 91.72 (7) | C4—N4—H17 | 125.8 |
O4i—Cu1—O3 | 107.31 (6) | C5—N3—Cu1 | 127.80 (16) |
O5i—Cu1—N1 | 88.52 (7) | C5—C6—N4 | 106.3 (2) |
O5i—Cu1—N3 | 91.83 (7) | C5—C6—H6 | 126.9 |
O5i—Cu1—O1 | 125.82 (7) | C6—N4—H17 | 125.8 |
O5i—Cu1—O3 | 158.76 (6) | C6—C5—N3 | 109.4 (2) |
O5i—Cu1—O4i | 51.45 (6) | C6—C5—H5 | 125.3 |
N1—C1—N2 | 110.8 (2) | C7—O1—Cu1 | 124.16 (15) |
N1—C1—H1 | 124.6 | C7—C8—H8A | 109.7 |
N1—C2—H2 | 125.2 | C7—C8—H8B | 109.7 |
N2—C1—H1 | 124.6 | C8—O3—Cu1 | 108.58 (13) |
N2—C3—H3 | 127.1 | C9—O3—Cu1 | 131.81 (13) |
N3—C4—N4 | 110.8 (2) | C9—O3—C8 | 119.59 (17) |
N3—C4—H4 | 124.6 | C9—C10—C11 | 118.5 (2) |
N3—C5—H5 | 125.3 | C9—C10—H10 | 120.8 |
N4—C4—H4 | 124.6 | C9—C14—H14 | 119.9 |
N4—C6—H6 | 126.9 | C10—C9—C14 | 120.8 (2) |
O1—C7—C8 | 119.82 (19) | C10—C11—H11 | 119.3 |
O2—C7—O1 | 123.7 (2) | C11—C10—H10 | 120.8 |
O2—C7—C8 | 116.5 (2) | C11—C12—C13 | 119.8 (2) |
O3—C8—C7 | 109.98 (19) | C11—C12—H12 | 120.1 |
O3—C8—H8A | 109.7 | C12—C11—C10 | 121.4 (2) |
O3—C8—H8B | 109.7 | C12—C11—H11 | 119.3 |
O3—C9—C10 | 123.8 (2) | C12—C13—C15 | 120.13 (19) |
O3—C9—C14 | 115.40 (18) | C13—C12—H12 | 120.1 |
O4—C15—C13 | 117.57 (18) | C13—C14—C9 | 120.18 (19) |
O5—C15—O4 | 123.6 (2) | C13—C14—H14 | 119.9 |
O5—C15—C13 | 118.85 (19) | C14—C13—C12 | 119.3 (2) |
C1—N1—C2 | 105.8 (2) | C14—C13—C15 | 120.53 (18) |
C1—N1—Cu1 | 125.38 (17) | C15—O4—Cu1i | 111.66 (13) |
C1—N2—C3 | 108.0 (2) | H1W1—O1W—H1W2 | 108.0 (16) |
C1—N2—H16 | 126.0 | H8A—C8—H8B | 108.2 |
C2—N1—Cu1 | 128.13 (18) | ||
Cu1—N1—C1—N2 | 171.33 (16) | O3—C9—C10—C11 | 178.8 (2) |
Cu1—N1—C2—C3 | −171.30 (18) | O3—C9—C14—C13 | −178.59 (19) |
Cu1—N3—C4—N4 | −167.86 (17) | O4i—Cu1—N1—C1 | 29.6 (2) |
Cu1—N3—C5—C6 | 167.67 (19) | O4i—Cu1—N1—C2 | −161.0 (2) |
Cu1—O1—C7—O2 | −172.42 (17) | O4i—Cu1—N3—C4 | −26.0 (2) |
Cu1—O1—C7—C8 | 8.4 (3) | O4i—Cu1—N3—C5 | 169.0 (2) |
Cu1—O3—C8—C7 | 14.1 (2) | O4i—Cu1—O3—C8 | 173.59 (15) |
Cu1—O3—C9—C10 | 175.81 (17) | O4i—Cu1—O3—C9 | −8.2 (2) |
Cu1—O3—C9—C14 | −4.3 (3) | C1—N1—C2—C3 | −0.3 (3) |
Cu1i—O4—C15—O5 | −10.1 (3) | C1—N2—C3—C2 | −0.4 (3) |
Cu1i—O4—C15—C13 | 168.75 (14) | C2—N1—C1—N2 | 0.0 (3) |
N1—Cu1—O1—C7 | 91.36 (18) | C3—N2—C1—N1 | 0.3 (3) |
N1—Cu1—O3—C8 | −97.64 (16) | C4—N3—C5—C6 | 0.2 (3) |
N1—Cu1—O3—C9 | 80.6 (2) | C4—N4—C6—C5 | 0.2 (3) |
N1—C2—C3—N2 | 0.4 (3) | C5—N3—C4—N4 | −0.1 (3) |
N3—Cu1—O1—C7 | −88.49 (18) | C6—N4—C4—N3 | −0.1 (3) |
N3—Cu1—O3—C8 | 82.10 (16) | C8—O3—C9—C10 | −6.1 (3) |
N3—Cu1—O3—C9 | −99.7 (2) | C8—O3—C9—C14 | 173.7 (2) |
N3—C5—C6—N4 | −0.3 (3) | C9—O3—C8—C7 | −164.43 (19) |
O1—Cu1—N1—C1 | −153.1 (2) | C9—C10—C11—C12 | 0.1 (4) |
O1—Cu1—N1—C2 | 16.3 (2) | C10—C9—C14—C13 | 1.3 (3) |
O1—Cu1—N3—C4 | 156.7 (2) | C10—C11—C12—C13 | 0.6 (4) |
O1—Cu1—N3—C5 | −8.3 (2) | C11—C12—C13—C14 | −0.4 (3) |
O1—Cu1—O3—C8 | −8.80 (15) | C11—C12—C13—C15 | 178.0 (2) |
O1—Cu1—O3—C9 | 169.4 (2) | C12—C13—C14—C9 | −0.5 (3) |
O1—C7—C8—O3 | −15.8 (3) | C12—C13—C15—O4 | 178.5 (2) |
O2—C7—C8—O3 | 164.9 (2) | C12—C13—C15—O5 | −2.7 (3) |
O3—Cu1—N1—C1 | −77.7 (2) | C14—C9—C10—C11 | −1.0 (4) |
O3—Cu1—N1—C2 | 91.7 (2) | C14—C13—C15—O4 | −3.2 (3) |
O3—Cu1—N3—C4 | 81.3 (2) | C14—C13—C15—O5 | 175.7 (2) |
O3—Cu1—N3—C5 | −83.7 (2) | C15—C13—C14—C9 | −178.87 (19) |
O3—Cu1—O1—C7 | 0.33 (17) |
Symmetry code: (i) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H16···O1W | 0.86 | 1.90 | 2.712 (3) | 158 |
N4—H17···O5ii | 0.86 | 1.96 | 2.812 (3) | 171 |
O1W—H1W1···O5iii | 0.85 (2) | 1.96 (3) | 2.802 (3) | 168 (4) |
O1W—H1W2···O2iv | 0.85 (2) | 1.84 (3) | 2.691 (3) | 172 (4) |
Symmetry codes: (ii) −x, y+1/2, −z+1/2; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y−1/2, −z+3/2. |
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