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The Cu atom in the title compound, [Cu(C
8H
7O
3)
2], lies on a center of inversion and exists in a square-planar enviroment that is defined by the four chelating O atoms. Intermolecular O—H
O hydrogen bonds [O
O = 2.711 (3)Å] link adjacent molecules into a layer structure.
Supporting information
CCDC reference: 277728
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.117
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT731_ALERT_1_C Bond Calc 0.83(3), Rep 0.830(10) ...... 3.00 su-Rat
O3 -H3O 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.83(3), Rep 0.830(10) ...... 3.00 su-Rat
O3 -H3O 1.555 1.555
PLAT736_ALERT_1_C H...A Calc 1.90(3), Rep 1.897(14) ...... 2.14 su-Rat
H3O -O2 1.555 3.466
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
5 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 138
included in the refinement in the riding-model approximation, with U~iso(H) set
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~
1 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, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; 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(2-acetyl-5-hydroxyphenolato-
κ2O,
O')copper(II)
top
Crystal data top
[Cu(C8H7O3)2] | F(000) = 748 |
Mr = 365.81 | Dx = 1.666 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 766 reflections |
a = 7.022 (1) Å | θ = 2.7–27.0° |
b = 13.667 (2) Å | µ = 1.53 mm−1 |
c = 15.192 (2) Å | T = 295 K |
V = 1458.1 (3) Å3 | Prism, dark brown |
Z = 4 | 0.24 × 0.14 × 0.11 mm |
Data collection top
Bruker SMART area-detector diffractometer | 1591 independent reflections |
Radiation source: medium-focus sealed tube | 1057 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
φ and ω scans | θmax = 27.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −6→8 |
Tmin = 0.724, Tmax = 0.850 | k = −17→17 |
8105 measured reflections | l = −18→19 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0694P)2 + 0.0274P] where P = (Fo2 + 2Fc2)/3 |
1591 reflections | (Δ/σ)max = 0.001 |
111 parameters | Δρmax = 0.35 e Å−3 |
1 restraint | Δρmin = −0.34 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.5000 | 0.5000 | 0.5000 | 0.0383 (2) | |
O1 | 0.3775 (3) | 0.4170 (1) | 0.5840 (1) | 0.0449 (5) | |
O2 | 0.3126 (3) | 0.5977 (1) | 0.5115 (1) | 0.0432 (5) | |
O3 | −0.2310 (3) | 0.7636 (2) | 0.6145 (2) | 0.0479 (6) | |
C1 | 0.1612 (4) | 0.3439 (2) | 0.6803 (2) | 0.0465 (7) | |
C2 | 0.2218 (4) | 0.4286 (2) | 0.6230 (2) | 0.0352 (6) | |
C3 | 0.1082 (4) | 0.5143 (2) | 0.6161 (2) | 0.0340 (6) | |
C4 | −0.0649 (5) | 0.5229 (2) | 0.6651 (2) | 0.0467 (7) | |
C5 | −0.1753 (4) | 0.6040 (2) | 0.6643 (2) | 0.0530 (8) | |
C6 | −0.1206 (4) | 0.6836 (2) | 0.6117 (2) | 0.0385 (7) | |
C7 | 0.0396 (4) | 0.6785 (2) | 0.5604 (2) | 0.0385 (6) | |
C8 | 0.1583 (4) | 0.5952 (2) | 0.5614 (2) | 0.0339 (6) | |
H3o | −0.199 (5) | 0.807 (2) | 0.579 (2) | 0.08 (1)* | |
H1a | 0.2632 | 0.2973 | 0.6841 | 0.070* | |
H1b | 0.0512 | 0.3130 | 0.6550 | 0.070* | |
H1c | 0.1306 | 0.3674 | 0.7381 | 0.070* | |
H4 | −0.1035 | 0.4700 | 0.6992 | 0.056* | |
H5 | −0.2856 | 0.6070 | 0.6980 | 0.064* | |
H7 | 0.0708 | 0.7310 | 0.5242 | 0.046* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0368 (3) | 0.0301 (3) | 0.0481 (3) | 0.0004 (19) | 0.0114 (2) | 0.0044 (2) |
O1 | 0.038 (1) | 0.036 (1) | 0.061 (1) | 0.002 (1) | 0.015 (1) | 0.012 (1) |
O2 | 0.041 (1) | 0.032 (1) | 0.057 (1) | 0.003 (1) | 0.019 (1) | 0.009 (1) |
O3 | 0.043 (1) | 0.050 (1) | 0.050 (1) | 0.015 (1) | 0.009 (1) | 0.010 (1) |
C1 | 0.040 (2) | 0.040 (2) | 0.059 (2) | −0.003 (1) | 0.002 (1) | 0.017 (1) |
C2 | 0.035 (2) | 0.035 (1) | 0.036 (1) | −0.007 (1) | −0.002 (1) | 0.001 (1) |
C3 | 0.032 (2) | 0.034 (2) | 0.037 (1) | −0.005 (1) | 0.003 (1) | 0.002 (1) |
C4 | 0.044 (2) | 0.043 (2) | 0.054 (2) | −0.000 (1) | 0.015 (2) | 0.014 (1) |
C5 | 0.040 (2) | 0.058 (2) | 0.061 (2) | 0.006 (1) | 0.018 (2) | 0.016 (2) |
C6 | 0.034 (2) | 0.042 (2) | 0.040 (2) | 0.005 (1) | −0.001 (1) | 0.000 (1) |
C7 | 0.042 (2) | 0.033 (2) | 0.048 (1) | 0.001 (1) | 0.004 (1) | 0.006 (1) |
C8 | 0.034 (1) | 0.031 (1) | 0.036 (1) | −0.003 (1) | 0.004 (1) | −0.001 (1) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.912 (2) | C4—C5 | 1.353 (4) |
Cu1—O1i | 1.912 (2) | C5—C6 | 1.403 (4) |
Cu1—O2 | 1.883 (2) | C6—C7 | 1.371 (4) |
Cu1—O2i | 1.883 (2) | C7—C8 | 1.411 (4) |
O1—C2 | 1.253 (3) | O3—H3o | 0.83 (1) |
O2—C8 | 1.323 (3) | C1—H1a | 0.96 |
O3—C6 | 1.342 (3) | C1—H1b | 0.96 |
C1—C2 | 1.510 (4) | C1—H1c | 0.96 |
C2—C3 | 1.420 (4) | C4—H4 | 0.93 |
C3—C8 | 1.427 (3) | C5—H5 | 0.93 |
C3—C4 | 1.430 (4) | C7—H7 | 0.93 |
| | | |
O1—Cu1—O1i | 180 | C7—C6—C5 | 120.6 (3) |
O1—Cu1—O2 | 92.53 (8) | C6—C7—C8 | 121.3 (2) |
O1—Cu1—O2i | 87.47 (8) | O2—C8—C7 | 117.1 (2) |
O1i—Cu1—O2 | 87.47 (8) | O2—C8—C3 | 123.8 (2) |
O1i—Cu1—O2i | 92.53 (8) | C7—C8—C3 | 119.1 (2) |
O2—Cu1—O2i | 180.000 (1) | C6—O3—H3o | 114 (3) |
C2—O1—Cu1 | 129.27 (18) | C2—C1—H1a | 109.5 |
C8—O2—Cu1 | 127.36 (16) | C2—C1—H1b | 109.5 |
O1—C2—C3 | 124.0 (2) | H1a—C1—H1b | 109.5 |
O1—C2—C1 | 114.9 (2) | C2—C1—H1c | 109.5 |
C3—C2—C1 | 121.1 (2) | H1a—C1—H1c | 109.5 |
C2—C3—C8 | 122.9 (2) | H1b—C1—H1c | 109.5 |
C2—C3—C4 | 120.4 (2) | C5—C4—H4 | 118.3 |
C8—C3—C4 | 116.7 (2) | C3—C4—H4 | 118.3 |
C5—C4—C3 | 123.3 (3) | C4—C5—H5 | 120.5 |
C4—C5—C6 | 118.9 (3) | C6—C5—H5 | 120.5 |
O3—C6—C7 | 122.3 (3) | C6—C7—H7 | 119.3 |
O3—C6—C5 | 117.1 (3) | C8—C7—H7 | 119.3 |
| | | |
O2—Cu1—O1—C2 | 4.5 (2) | C4—C5—C6—O3 | −178.3 (3) |
O2i—Cu1—O1—C2 | −175.5 (2) | C4—C5—C6—C7 | 1.5 (5) |
O1—Cu1—O2—C8 | −1.7 (2) | O3—C6—C7—C8 | 177.2 (3) |
O1i—Cu1—O2—C8 | 178.3 (2) | C5—C6—C7—C8 | −2.5 (4) |
Cu1—O1—C2—C3 | −5.2 (4) | Cu1—O2—C8—C7 | 178.9 (2) |
Cu1—O1—C2—C1 | 175.4 (2) | Cu1—O2—C8—C3 | −0.2 (4) |
O1—C2—C3—C8 | 2.0 (4) | C6—C7—C8—O2 | −178.3 (2) |
C1—C2—C3—C8 | −178.7 (3) | C6—C7—C8—C3 | 0.9 (4) |
O1—C2—C3—C4 | −178.0 (3) | C2—C3—C8—O2 | 0.8 (4) |
C1—C2—C3—C4 | 1.4 (4) | C4—C3—C8—O2 | −179.3 (3) |
C2—C3—C4—C5 | 177.1 (3) | C2—C3—C8—C7 | −178.3 (3) |
C8—C3—C4—C5 | −2.8 (5) | C4—C3—C8—C7 | 1.7 (4) |
C3—C4—C5—C6 | 1.2 (5) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3o···O2ii | 0.83 (1) | 1.90 (1) | 2.710 (3) | 166 (4) |
Symmetry code: (ii) x−1/2, −y+3/2, −z+1. |
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