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The title centrosymmetric compound, [Cu
2(C
8H
7O
3)
4(C
2H
3N)
2], is a carboxylate-bridged dinuclear Cu
II complex with four phenoxyacetate and two acetonitrile molecules as ligands. Each of the four phenoxyacetate anions straddles the pair of Cu atoms, the Cu—Cu distance being 2.6618 (10) Å. A weak C—H
π interaction connects the dinuclear Cu
II units into a one-dimensional chain.
Supporting information
CCDC reference: 282517
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.053
- wR factor = 0.114
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
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
2 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
0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 178
for the Cu^II~ atom. The Cu---N distance is 2.188(3) \%A.
If you require a ~ then it should be escaped
with a \, i.e. \~
Otherwise there must be a matching closing ~, e.g. C~2~H~4~
PUBL023_ALERT_1_A There is a mismatched ^ on line 178
for the Cu^II~ atom. The Cu---N distance is 2.188(3) \%A.
If you require a ^ then it should be escaped
with a \, i.e. \^
Otherwise there must be a matching closing ~, e.g. ^12^C
2 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
Tetra-µ-phenoxyacetato-bis[(acetonitrile)copper(II)](Cu—Cu)
top
Crystal data top
[Cu2(C8H7O3)4(C2H3N)2] | F(000) = 1672 |
Mr = 813.73 | Dx = 1.497 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 935 reflections |
a = 19.064 (4) Å | θ = 2.4–25.6° |
b = 7.6978 (16) Å | µ = 1.24 mm−1 |
c = 24.864 (5) Å | T = 293 K |
β = 98.261 (4)° | Prism, blue |
V = 3611.0 (13) Å3 | 0.23 × 0.20 × 0.18 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3544 independent reflections |
Radiation source: fine-focus sealed tube | 2539 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
φ and ω scans | θmax = 26.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −22→23 |
Tmin = 0.75, Tmax = 0.79 | k = −9→9 |
9410 measured reflections | l = −24→30 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.05P)2 + 1.55P] where P = (Fo2 + 2Fc2)/3 |
3544 reflections | (Δ/σ)max < 0.001 |
236 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.53 e Å−3 |
Special details top
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) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.81212 (2) | 0.32945 (6) | 0.013022 (18) | 0.03285 (15) | |
C1 | 0.6783 (2) | 0.0223 (6) | 0.21818 (16) | 0.0431 (10) | |
C2 | 0.6205 (2) | −0.0779 (6) | 0.22640 (17) | 0.0443 (10) | |
H2 | 0.5960 | −0.1420 | 0.1980 | 0.053* | |
C3 | 0.5996 (2) | −0.0816 (6) | 0.27735 (17) | 0.0452 (11) | |
H3 | 0.5616 | −0.1518 | 0.2831 | 0.054* | |
C4 | 0.6333 (2) | 0.0155 (6) | 0.31984 (17) | 0.0439 (10) | |
H4 | 0.6181 | 0.0140 | 0.3538 | 0.053* | |
C5 | 0.6893 (2) | 0.1133 (6) | 0.31049 (17) | 0.0437 (10) | |
H5 | 0.7125 | 0.1806 | 0.3386 | 0.052* | |
C6 | 0.7132 (2) | 0.1167 (5) | 0.26066 (15) | 0.0389 (9) | |
H6 | 0.7528 | 0.1825 | 0.2559 | 0.047* | |
C7 | 0.7515 (2) | 0.1232 (6) | 0.15558 (17) | 0.0449 (10) | |
H7A | 0.7958 | 0.0693 | 0.1712 | 0.054* | |
H7B | 0.7487 | 0.2358 | 0.1726 | 0.054* | |
C8 | 0.75154 (19) | 0.1477 (5) | 0.09627 (15) | 0.0332 (8) | |
C9 | 0.5631 (2) | 0.5850 (6) | 0.08775 (17) | 0.0438 (10) | |
C10 | 0.4899 (2) | 0.5655 (5) | 0.08751 (17) | 0.0427 (10) | |
H10 | 0.4583 | 0.6051 | 0.0581 | 0.051* | |
C11 | 0.4645 (2) | 0.4866 (6) | 0.13135 (18) | 0.0463 (11) | |
H11 | 0.4161 | 0.4714 | 0.1310 | 0.056* | |
C12 | 0.5116 (2) | 0.4313 (6) | 0.17521 (17) | 0.0466 (11) | |
H12 | 0.4945 | 0.3808 | 0.2048 | 0.056* | |
C13 | 0.5833 (2) | 0.4498 (5) | 0.17594 (19) | 0.0474 (11) | |
H13 | 0.6147 | 0.4115 | 0.2057 | 0.057* | |
C14 | 0.6090 (2) | 0.5260 (6) | 0.13183 (18) | 0.0490 (11) | |
H14 | 0.6576 | 0.5372 | 0.1321 | 0.059* | |
C15 | 0.6522 (2) | 0.6853 (5) | 0.03840 (16) | 0.0407 (10) | |
H15A | 0.6765 | 0.7317 | 0.0723 | 0.049* | |
H15B | 0.6568 | 0.7696 | 0.0101 | 0.049* | |
C16 | 0.6884 (2) | 0.5191 (5) | 0.02549 (16) | 0.0340 (8) | |
C17 | 0.9669 (2) | 0.5165 (6) | 0.05842 (16) | 0.0433 (10) | |
C18 | 1.0326 (2) | 0.5880 (6) | 0.08238 (16) | 0.0433 (10) | |
H18A | 1.0312 | 0.6104 | 0.1202 | 0.065* | |
H18B | 1.0411 | 0.6947 | 0.0644 | 0.065* | |
H18C | 1.0701 | 0.5074 | 0.0788 | 0.065* | |
N1 | 0.91345 (16) | 0.4579 (4) | 0.03998 (13) | 0.0366 (7) | |
O1 | 0.80321 (14) | 0.2296 (4) | 0.08406 (10) | 0.0423 (7) | |
O2 | 0.69920 (13) | 0.0979 (4) | 0.06349 (10) | 0.0372 (6) | |
O3 | 0.69484 (13) | 0.0197 (4) | 0.16691 (11) | 0.0377 (6) | |
O4 | 0.75506 (13) | 0.5273 (4) | 0.03105 (12) | 0.0450 (7) | |
O5 | 0.65126 (13) | 0.3906 (3) | 0.00956 (10) | 0.0343 (6) | |
O6 | 0.58037 (14) | 0.6658 (4) | 0.04285 (11) | 0.0442 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0295 (2) | 0.0334 (3) | 0.0357 (3) | −0.0055 (2) | 0.00514 (18) | 0.0016 (2) |
C1 | 0.045 (2) | 0.047 (3) | 0.038 (2) | 0.007 (2) | 0.0066 (19) | 0.0188 (19) |
C2 | 0.049 (3) | 0.044 (2) | 0.043 (2) | −0.0031 (19) | 0.014 (2) | 0.0203 (19) |
C3 | 0.049 (2) | 0.049 (3) | 0.043 (2) | 0.007 (2) | 0.023 (2) | 0.025 (2) |
C4 | 0.044 (2) | 0.045 (3) | 0.044 (2) | 0.020 (2) | 0.015 (2) | 0.012 (2) |
C5 | 0.047 (2) | 0.043 (3) | 0.040 (2) | 0.0115 (19) | 0.0032 (19) | 0.0119 (18) |
C6 | 0.036 (2) | 0.044 (2) | 0.036 (2) | 0.0063 (18) | 0.0043 (17) | 0.0127 (18) |
C7 | 0.047 (2) | 0.041 (3) | 0.046 (2) | −0.0252 (19) | 0.0022 (18) | 0.0063 (19) |
C8 | 0.0324 (19) | 0.0247 (19) | 0.043 (2) | 0.0009 (15) | 0.0077 (16) | 0.0062 (16) |
C9 | 0.043 (2) | 0.045 (3) | 0.046 (2) | −0.0020 (19) | 0.013 (2) | 0.0120 (19) |
C10 | 0.041 (2) | 0.045 (2) | 0.046 (2) | 0.0151 (19) | 0.0191 (19) | 0.0140 (19) |
C11 | 0.041 (2) | 0.050 (3) | 0.054 (3) | 0.009 (2) | 0.028 (2) | 0.011 (2) |
C12 | 0.047 (3) | 0.059 (3) | 0.039 (2) | 0.030 (2) | 0.0254 (19) | 0.0163 (19) |
C13 | 0.045 (2) | 0.043 (3) | 0.052 (3) | 0.012 (2) | 0.000 (2) | −0.015 (2) |
C14 | 0.047 (3) | 0.047 (3) | 0.050 (2) | 0.005 (2) | −0.005 (2) | −0.005 (2) |
C15 | 0.052 (2) | 0.031 (2) | 0.046 (2) | 0.0023 (18) | 0.0292 (19) | −0.0056 (17) |
C16 | 0.038 (2) | 0.0196 (18) | 0.044 (2) | 0.0045 (16) | 0.0042 (17) | 0.0020 (16) |
C17 | 0.035 (2) | 0.050 (3) | 0.040 (2) | −0.0033 (19) | −0.0128 (17) | −0.0111 (19) |
C18 | 0.039 (2) | 0.049 (3) | 0.043 (2) | −0.0153 (19) | 0.0099 (18) | −0.0269 (19) |
N1 | 0.0250 (16) | 0.044 (2) | 0.0415 (18) | −0.0050 (14) | 0.0076 (14) | 0.0034 (15) |
O1 | 0.0392 (15) | 0.0535 (18) | 0.0345 (15) | −0.0142 (13) | 0.0068 (12) | 0.0076 (12) |
O2 | 0.0367 (15) | 0.0422 (16) | 0.0318 (14) | −0.0043 (12) | 0.0019 (11) | 0.0059 (12) |
O3 | 0.0219 (12) | 0.0430 (16) | 0.0476 (15) | −0.0167 (11) | 0.0022 (11) | −0.0062 (13) |
O4 | 0.0277 (14) | 0.0358 (17) | 0.074 (2) | −0.0099 (11) | 0.0139 (13) | −0.0125 (14) |
O5 | 0.0272 (13) | 0.0384 (16) | 0.0371 (14) | −0.0058 (11) | 0.0036 (11) | −0.0015 (11) |
O6 | 0.0405 (15) | 0.0493 (17) | 0.0464 (16) | 0.0138 (13) | 0.0191 (13) | 0.0111 (14) |
Geometric parameters (Å, º) top
Cu1—O5i | 1.946 (3) | C9—C14 | 1.377 (6) |
Cu1—O1 | 1.956 (3) | C9—C10 | 1.403 (5) |
Cu1—O4 | 1.961 (3) | C10—C11 | 1.394 (5) |
Cu1—O2i | 1.965 (3) | C10—H10 | 0.9300 |
Cu1—N1 | 2.188 (3) | C11—C12 | 1.376 (6) |
Cu1—Cu1i | 2.6618 (10) | C11—H11 | 0.9300 |
C1—O3 | 1.357 (5) | C12—C13 | 1.373 (6) |
C1—C6 | 1.373 (6) | C12—H12 | 0.9300 |
C1—C2 | 1.384 (6) | C13—C14 | 1.393 (6) |
C2—C3 | 1.382 (5) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—H14 | 0.9300 |
C3—C4 | 1.376 (6) | C15—O6 | 1.397 (5) |
C3—H3 | 0.9300 | C15—C16 | 1.510 (5) |
C4—C5 | 1.354 (6) | C15—H15A | 0.9700 |
C4—H4 | 0.9300 | C15—H15B | 0.9700 |
C5—C6 | 1.381 (5) | C16—O5 | 1.247 (4) |
C5—H5 | 0.9300 | C16—O4 | 1.261 (4) |
C6—H6 | 0.9300 | C17—N1 | 1.148 (5) |
C7—O3 | 1.403 (4) | C17—C18 | 1.419 (5) |
C7—C8 | 1.487 (5) | C18—H18A | 0.9600 |
C7—H7A | 0.9700 | C18—H18B | 0.9600 |
C7—H7B | 0.9700 | C18—H18C | 0.9600 |
C8—O1 | 1.244 (4) | O2—Cu1i | 1.965 (3) |
C8—O2 | 1.254 (4) | O5—Cu1i | 1.946 (3) |
C9—O6 | 1.359 (4) | | |
| | | |
O5i—Cu1—O1 | 89.99 (12) | O6—C9—C14 | 127.1 (4) |
O5i—Cu1—O4 | 167.49 (10) | O6—C9—C10 | 113.8 (4) |
O1—Cu1—O4 | 88.61 (12) | C14—C9—C10 | 119.1 (4) |
O5i—Cu1—O2i | 87.85 (11) | C11—C10—C9 | 120.0 (4) |
O1—Cu1—O2i | 167.03 (11) | C11—C10—H10 | 120.0 |
O4—Cu1—O2i | 90.74 (12) | C9—C10—H10 | 120.0 |
O5i—Cu1—N1 | 98.30 (11) | C12—C11—C10 | 119.7 (4) |
O1—Cu1—N1 | 95.07 (11) | C12—C11—H11 | 120.2 |
O4—Cu1—N1 | 94.21 (12) | C10—C11—H11 | 120.2 |
O2i—Cu1—N1 | 97.89 (11) | C13—C12—C11 | 120.9 (4) |
O5i—Cu1—Cu1i | 82.72 (7) | C13—C12—H12 | 119.6 |
O1—Cu1—Cu1i | 81.34 (8) | C11—C12—H12 | 119.6 |
O4—Cu1—Cu1i | 84.78 (8) | C12—C13—C14 | 119.7 (4) |
O2i—Cu1—Cu1i | 85.71 (8) | C12—C13—H13 | 120.2 |
N1—Cu1—Cu1i | 176.28 (9) | C14—C13—H13 | 120.2 |
O3—C1—C6 | 125.3 (4) | C9—C14—C13 | 120.7 (4) |
O3—C1—C2 | 115.4 (4) | C9—C14—H14 | 119.6 |
C6—C1—C2 | 119.3 (4) | C13—C14—H14 | 119.6 |
C3—C2—C1 | 119.2 (4) | O6—C15—C16 | 114.1 (3) |
C3—C2—H2 | 120.4 | O6—C15—H15A | 108.7 |
C1—C2—H2 | 120.4 | C16—C15—H15A | 108.7 |
C4—C3—C2 | 121.9 (4) | O6—C15—H15B | 108.7 |
C4—C3—H3 | 119.1 | C16—C15—H15B | 108.7 |
C2—C3—H3 | 119.1 | H15A—C15—H15B | 107.6 |
C5—C4—C3 | 117.6 (4) | O5—C16—O4 | 126.3 (3) |
C5—C4—H4 | 121.2 | O5—C16—C15 | 119.0 (3) |
C3—C4—H4 | 121.2 | O4—C16—C15 | 114.7 (3) |
C4—C5—C6 | 122.4 (4) | N1—C17—C18 | 178.7 (5) |
C4—C5—H5 | 118.8 | C17—C18—H18A | 109.5 |
C6—C5—H5 | 118.8 | C17—C18—H18B | 109.5 |
C1—C6—C5 | 119.6 (4) | H18A—C18—H18B | 109.5 |
C1—C6—H6 | 120.2 | C17—C18—H18C | 109.5 |
C5—C6—H6 | 120.2 | H18A—C18—H18C | 109.5 |
O3—C7—C8 | 112.4 (3) | H18B—C18—H18C | 109.5 |
O3—C7—H7A | 109.1 | C17—N1—Cu1 | 173.7 (3) |
C8—C7—H7A | 109.1 | C8—O1—Cu1 | 126.5 (3) |
O3—C7—H7B | 109.1 | C8—O2—Cu1i | 120.6 (2) |
C8—C7—H7B | 109.1 | C1—O3—C7 | 118.1 (3) |
H7A—C7—H7B | 107.9 | C16—O4—Cu1 | 121.3 (2) |
O1—C8—O2 | 125.5 (4) | C16—O5—Cu1i | 124.9 (2) |
O1—C8—C7 | 114.8 (3) | C9—O6—C15 | 118.0 (3) |
O2—C8—C7 | 119.5 (3) | | |
Symmetry code: (i) −x+3/2, −y+1/2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15B···Cg1ii | 0.97 | 2.87 | 3.61 | 134 |
Symmetry code: (ii) x, y−1, z. |
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