The asymmetric unit of the title complex, [Cu(C
2H
3O
2)
2(C
5H
5NO)
2], consists of two half-units of [Cu(ac)
2(3-PyOH)
2] (ac is acetate and 3-PyOH is 3-hydroxypyridine). The two molecules in the unit cell are held together
via hydrogen bonds in a chain structure; the Cu
Cu separation is 5.482 (2) Å. The Cu
II atoms in the two neutral units lie on special positions with inversion symmetry, and both show elongated octahedral geometry, defined by four acetate O atoms and two
endo-N atoms of two 3-PyOH ligands.
Supporting information
CCDC reference: 252744
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.039
- wR factor = 0.108
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu1 - O2 .. 11.54 su
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C10 .. 5.27 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O1 .. 5.79 su
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
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.
diacetatobis(3-hydroxypyridine)copper(II)
top
Crystal data top
[Cu(C2H3O2)2(C5H5NO)2] | Z = 2 |
Mr = 371.83 | F(000) = 382 |
Triclinic, P1 | Dx = 1.546 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9725 (18) Å | Cell parameters from 7857 reflections |
b = 10.138 (2) Å | θ = 3.4–27.5° |
c = 10.247 (2) Å | µ = 1.40 mm−1 |
α = 114.92 (3)° | T = 293 K |
β = 100.20 (3)° | Prism, blue |
γ = 100.07 (3)° | 0.39 × 0.28 × 0.18 mm |
V = 798.8 (4) Å3 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 3601 independent reflections |
Radiation source: fine-focus sealed tube | 2890 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.4° |
ω scans | h = −11→10 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −13→13 |
Tmin = 0.631, Tmax = 0.778 | l = −12→13 |
7445 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0653P)2 + 0.1657P] where P = (Fo2 + 2Fc2)/3 |
3601 reflections | (Δ/σ)max < 0.001 |
219 parameters | Δρmax = 0.53 e Å−3 |
2 restraints | Δρmin = −0.42 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 | 0.0000 | 0.0000 | 0.0000 | 0.0347 (1) | |
Cu2 | 0.0000 | 0.5000 | 0.5000 | 0.0347 (1) | |
O1 | 0.1748 (2) | −0.0948 (2) | −0.0258 (2) | 0.0434 (4) | |
O2 | 0.2423 (2) | 0.0609 (2) | 0.2163 (2) | 0.0532 (5) | |
O3 | 0.1855 (3) | 0.5584 (2) | 0.0742 (2) | 0.0512 (5) | |
H15 | 0.156 (4) | 0.571 (4) | 0.152 (3) | 0.077* | |
O4 | 0.0856 (2) | 0.7116 (2) | 0.5423 (2) | 0.0407 (4) | |
O5 | 0.0886 (2) | 0.5812 (2) | 0.3087 (2) | 0.0492 (4) | |
O6 | 0.4440 (2) | 0.2151 (2) | 0.4832 (2) | 0.0585 (5) | |
H16 | 0.380 (4) | 0.157 (4) | 0.397 (2) | 0.088* | |
N1 | 0.1058 (2) | 0.1543 (2) | −0.0518 (2) | 0.0363 (4) | |
N2 | 0.2198 (2) | 0.4905 (2) | 0.5722 (2) | 0.0379 (4) | |
C1 | 0.4120 (4) | −0.0927 (4) | 0.1238 (4) | 0.0602 (8) | |
H1A | 0.4778 | −0.0332 | 0.2251 | 0.090* | |
H1B | 0.4698 | −0.0832 | 0.0563 | 0.090* | |
H1C | 0.3798 | −0.1971 | 0.1016 | 0.090* | |
C2 | 0.2685 (3) | −0.0372 (3) | 0.1053 (3) | 0.0418 (6) | |
C3 | 0.1072 (3) | 0.2990 (3) | 0.0243 (3) | 0.0377 (5) | |
H3 | 0.0571 | 0.3254 | 0.0999 | 0.045* | |
C4 | 0.1806 (3) | 0.4115 (3) | −0.0055 (3) | 0.0386 (5) | |
C5 | 0.2525 (4) | 0.3710 (3) | −0.1190 (3) | 0.0503 (6) | |
H5 | 0.3024 | 0.4436 | −0.1418 | 0.060* | |
C6 | 0.2497 (4) | 0.2205 (3) | −0.1989 (3) | 0.0536 (7) | |
H6 | 0.2973 | 0.1910 | −0.2763 | 0.064* | |
C7 | 0.1755 (3) | 0.1151 (3) | −0.1622 (3) | 0.0459 (6) | |
H7 | 0.1739 | 0.0143 | −0.2157 | 0.055* | |
C8 | 0.1823 (4) | 0.8520 (3) | 0.4233 (4) | 0.0587 (8) | |
H8A | 0.2948 | 0.8718 | 0.4431 | 0.088* | |
H8B | 0.1574 | 0.9327 | 0.5000 | 0.088* | |
H8C | 0.1383 | 0.8453 | 0.3275 | 0.088* | |
C9 | 0.1141 (3) | 0.7044 (3) | 0.4223 (3) | 0.0391 (5) | |
C10 | 0.2582 (3) | 0.3611 (3) | 0.5050 (3) | 0.0398 (5) | |
H10 | 0.1825 | 0.2779 | 0.4249 | 0.048* | |
C11 | 0.4070 (3) | 0.3470 (3) | 0.5509 (3) | 0.0415 (5) | |
C12 | 0.5187 (3) | 0.4709 (3) | 0.6690 (3) | 0.0476 (6) | |
H12 | 0.6197 | 0.4651 | 0.7019 | 0.057* | |
C13 | 0.4784 (3) | 0.6037 (3) | 0.7376 (3) | 0.0479 (6) | |
H13 | 0.5523 | 0.6883 | 0.8178 | 0.058* | |
C14 | 0.3284 (3) | 0.6108 (3) | 0.6872 (3) | 0.0447 (6) | |
H14 | 0.3022 | 0.7009 | 0.7339 | 0.054* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0386 (2) | 0.0294 (2) | 0.0351 (2) | 0.0091 (2) | 0.0102 (2) | 0.0145 (2) |
Cu2 | 0.0364 (2) | 0.0328 (2) | 0.0343 (2) | 0.0106 (2) | 0.0099 (2) | 0.0149 (2) |
O1 | 0.0448 (9) | 0.0421 (9) | 0.046 (1) | 0.0138 (8) | 0.0119 (8) | 0.0220 (8) |
O2 | 0.052 (1) | 0.047 (1) | 0.049 (1) | 0.0191 (9) | 0.0102 (9) | 0.0121 (9) |
O3 | 0.069 (1) | 0.0343 (9) | 0.051 (1) | 0.0119 (9) | 0.020 (1) | 0.0206 (9) |
O4 | 0.0426 (9) | 0.0372 (9) | 0.041 (1) | 0.0111 (7) | 0.0122 (7) | 0.0174 (8) |
O5 | 0.064 (1) | 0.0381 (9) | 0.042 (1) | 0.0119 (8) | 0.0185 (9) | 0.0155 (8) |
O6 | 0.054 (1) | 0.059 (1) | 0.053 (1) | 0.030 (1) | 0.0071 (9) | 0.015 (1) |
N1 | 0.038 (1) | 0.035 (1) | 0.039 (1) | 0.0112 (8) | 0.0108 (8) | 0.0186 (9) |
N2 | 0.040 (1) | 0.037 (1) | 0.039 (1) | 0.0135 (9) | 0.0114 (9) | 0.0191 (9) |
C1 | 0.050 (2) | 0.067 (2) | 0.070 (2) | 0.029 (2) | 0.017 (2) | 0.034 (2) |
C2 | 0.042 (1) | 0.037 (1) | 0.051 (2) | 0.010 (1) | 0.015 (1) | 0.023 (1) |
C3 | 0.040 (1) | 0.037 (1) | 0.034 (1) | 0.010 (1) | 0.012 (1) | 0.014 (1) |
C4 | 0.042 (1) | 0.035 (1) | 0.037 (1) | 0.009 (1) | 0.005 (1) | 0.019 (1) |
C5 | 0.064 (2) | 0.048 (2) | 0.052 (2) | 0.015 (1) | 0.026 (1) | 0.032 (1) |
C6 | 0.069 (2) | 0.054 (2) | 0.055 (2) | 0.026 (1) | 0.035 (1) | 0.032 (1) |
C7 | 0.058 (2) | 0.041 (1) | 0.046 (2) | 0.020 (1) | 0.021 (1) | 0.021 (1) |
C8 | 0.074 (2) | 0.044 (2) | 0.060 (2) | 0.010 (1) | 0.021 (2) | 0.027 (1) |
C9 | 0.036 (1) | 0.039 (1) | 0.043 (1) | 0.010 (1) | 0.009 (1) | 0.020 (1) |
C10 | 0.037 (1) | 0.042 (1) | 0.036 (1) | 0.009 (1) | 0.009 (1) | 0.016 (1) |
C11 | 0.043 (1) | 0.048 (1) | 0.037 (1) | 0.016 (1) | 0.012 (1) | 0.021 (1) |
C12 | 0.037 (1) | 0.060 (2) | 0.044 (2) | 0.011 (1) | 0.006 (1) | 0.027 (1) |
C13 | 0.042 (1) | 0.047 (1) | 0.042 (1) | 0.004 (1) | 0.001 (1) | 0.016 (1) |
C14 | 0.047 (1) | 0.037 (1) | 0.042 (1) | 0.007 (1) | 0.006 (1) | 0.015 (1) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.979 (2) | C1—C2 | 1.506 (4) |
Cu1—N1i | 1.997 (2) | C1—H1A | 0.9600 |
Cu1—O2i | 2.586 (2) | C1—H1B | 0.9600 |
Cu2—O4 | 1.975 (2) | C1—H1C | 0.9600 |
Cu2—O5 | 2.614 (2) | C3—C4 | 1.389 (3) |
Cu2—N2 | 2.014 (2) | C3—H3 | 0.9300 |
O1—C2 | 1.272 (3) | C4—C5 | 1.376 (4) |
O2—C2 | 1.249 (3) | C5—C6 | 1.387 (4) |
O4—C9 | 1.275 (3) | C5—H5 | 0.9300 |
O5—C9 | 1.244 (3) | C6—C7 | 1.381 (4) |
Cu1—O1i | 1.979 (2) | C6—H6 | 0.9300 |
Cu1—N1 | 1.997 (2) | C7—H7 | 0.9300 |
Cu1—O2 | 2.586 (2) | C8—C9 | 1.509 (4) |
Cu2—O4ii | 1.975 (2) | C8—H8A | 0.9600 |
Cu2—O5ii | 2.614 (2) | C8—H8B | 0.9600 |
Cu2—N2ii | 2.014 (2) | C8—H8C | 0.9600 |
O3—C4 | 1.351 (3) | C10—C11 | 1.388 (3) |
O3—H15 | 0.85 (3) | C10—H10 | 0.9300 |
O6—C11 | 1.354 (3) | C11—C12 | 1.377 (4) |
O6—H16 | 0.85 (1) | C12—C13 | 1.378 (4) |
N1—C3 | 1.337 (3) | C12—H12 | 0.9300 |
N1—C7 | 1.337 (3) | C13—C14 | 1.380 (4) |
N2—C14 | 1.338 (3) | C13—H13 | 0.9300 |
N2—C10 | 1.339 (3) | C14—H14 | 0.9300 |
| | | |
O1—Cu1—O2 | 55.76 (7) | N2—C10—H10 | 118.9 |
O1—Cu1—N1 | 89.89 (8) | N2—C14—C13 | 121.2 (2) |
O2—Cu1—N1 | 93.72 (8) | N2—C14—H14 | 119.4 |
O4—Cu2—O5 | 55.23 (7) | N2—Cu2—N2ii | 180.0 |
O4—Cu2—N2 | 90.02 (8) | C2—O1—Cu1 | 105.2 (2) |
N2—Cu2—O5 | 89.87 (8) | C4—O3—H15 | 110 (2) |
N1—Cu1—N1i | 180.0 (3) | C2—O2—Cu1 | 77.5 (2) |
N2—Cu2—N2ii | 180.0 (3) | C9—O5—Cu2 | 77.0 (2) |
O1—Cu1—O1i | 180.00 (9) | C9—O4—Cu2 | 106.0 (2) |
O1i—Cu1—N1i | 89.89 (8) | C11—O6—H16 | 112 (3) |
O1—Cu1—O2i | 124.3 (3) | C3—N1—C7 | 119.1 (2) |
O4—Cu2—O5ii | 124.8 (3) | C3—N1—Cu1 | 119.9 (2) |
O4ii—Cu2—N2 | 89.98 (8) | C7—N1—Cu1 | 121.0 (2) |
O1i—Cu1—N1 | 90.11 (8) | C14—N2—C10 | 119.2 (2) |
O1—Cu1—N1i | 90.11 (8) | C14—N2—Cu2 | 121.3 (2) |
O1i—Cu1—O2 | 124.3 (3) | C10—N2—Cu2 | 119.5 (2) |
O1i—Cu1—O2i | 55.76 (7) | C2—C1—H1A | 109.5 |
O1—C2—C1 | 117.9 (3) | C2—C1—H1B | 109.5 |
O2—Cu1—O2i | 180.0 (3) | C2—C1—H1C | 109.5 |
O2—C2—O1 | 121.6 (2) | C4—C3—H3 | 118.8 |
O2—C2—C1 | 120.5 (3) | C4—C5—C6 | 119.2 (2) |
O3—C4—C5 | 119.3 (2) | C4—C5—H5 | 120.4 |
O3—C4—C3 | 122.4 (2) | C5—C4—C3 | 118.3 (2) |
O4—Cu2—O4ii | 180.0 | C5—C6—H6 | 120.4 |
O4ii—Cu2—O5ii | 55.23 (7) | C6—C5—H5 | 120.4 |
O4ii—Cu2—O5 | 124.8 (3) | C6—C7—H7 | 119.2 |
O4—Cu2—N2ii | 89.98 (8) | C7—C6—C5 | 119.2 (3) |
O4ii—Cu2—N2ii | 90.02 (8) | C7—C6—H6 | 120.4 |
O4—C9—C8 | 117.4 (2) | C9—C8—H8A | 109.5 |
O5—Cu2—O5ii | 180.0 (3) | C9—C8—H8B | 109.5 |
O5—C9—O4 | 121.8 (2) | C9—C8—H8C | 109.5 |
O5—C9—C8 | 120.8 (3) | C11—C10—H10 | 118.9 |
O6—C11—C12 | 119.7 (2) | C11—C12—C13 | 118.9 (2) |
O6—C11—C10 | 121.7 (2) | C11—C12—H12 | 120.6 |
N1—Cu1—O2i | 86.3 (2) | C12—C11—C10 | 118.6 (2) |
N1i—Cu1—O2 | 86.3 (2) | C12—C13—C14 | 119.9 (2) |
N1i—Cu1—O2i | 93.72 (8) | C12—C13—H13 | 120.0 |
N1i—Cu1—N1 | 180.0 (1) | C13—C12—H12 | 120.6 |
N1—C3—C4 | 122.5 (2) | C13—C14—H14 | 119.4 |
N1—C3—H3 | 118.8 | C14—C13—H13 | 120.0 |
N1—C7—C6 | 121.6 (2) | H1A—C1—H1B | 109.5 |
N1—C7—H7 | 119.2 | H1A—C1—H1C | 109.5 |
N2—Cu2—O5ii | 90.1 (2) | H1B—C1—H1C | 109.5 |
N2ii—Cu2—O5ii | 89.87 (8) | H8A—C8—H8B | 109.5 |
N2ii—Cu2—O5 | 90.1 (2) | H8A—C8—H8C | 109.5 |
N2—C10—C11 | 122.2 (2) | H8B—C8—H8C | 109.5 |
| | | |
Cu1—O1—C2—O2 | −1.7 (3) | N1i—Cu1—O1—C2 | −84.6 (2) |
Cu1—O1—C2—C1 | 177.4 (2) | N1—Cu1—O1—C2 | 95.4 (2) |
Cu1—N1—C3—C4 | 179.2 (2) | N1—C3—C4—O3 | −178.2 (2) |
Cu1—N1—C7—C6 | −179.7 (2) | N1—C3—C4—C5 | 0.8 (4) |
Cu2—O4—C9—O5 | −0.4 (3) | N2—Cu2—O4—C9 | 90.0 (2) |
Cu2—O4—C9—C8 | −179.6 (2) | N2ii—Cu2—O4—C9 | −90.0 (2) |
Cu2—N2—C10—C11 | −179.2 (2) | N2—C10—C11—O6 | 179.3 (2) |
Cu2—N2—C14—C13 | 179.3 (2) | N2—C10—C11—C12 | −0.5 (4) |
O1—Cu1—N1—C3 | −139.2 (2) | C3—N1—C7—C6 | 0.5 (4) |
O1i—Cu1—N1—C3 | 40.8 (2) | C3—C4—C5—C6 | −0.2 (4) |
O1—Cu1—N1—C7 | 40.9 (2) | C4—C5—C6—C7 | −0.3 (5) |
O1i—Cu1—N1—C7 | −139.1 (2) | C5—C6—C7—N1 | 0.2 (4) |
O3—C4—C5—C6 | 178.9 (3) | C7—N1—C3—C4 | −1.0 (4) |
O4—Cu2—N2—C14 | 36.2 (2) | C10—N2—C14—C13 | −0.2 (4) |
O4ii—Cu2—N2—C14 | −143.8 (2) | C10—C11—C12—C13 | 0.4 (4) |
O4—Cu2—N2—C10 | −144.4 (2) | C11—C12—C13—C14 | −0.3 (4) |
O4ii—Cu2—N2—C10 | 35.6 (2) | C12—C13—C14—N2 | 0.2 (4) |
O6—C11—C12—C13 | −179.3 (3) | C14—N2—C10—C11 | 0.3 (4) |
Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H15···O5 | 0.85 (3) | 1.78 (3) | 2.632 (3) | 175 (4) |
O6—H16···O2 | 0.85 (3) | 1.78 (1) | 2.618 (3) | 171 (4) |