Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680706237X/lx2035sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680706237X/lx2035Isup2.hkl |
CCDC reference: 672768
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.048
- wR factor = 0.117
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
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 1 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 0 ALERT type 5 Informative message, check
For the applications of the title compound, see: Soldatov et al. (2003). For the synthesis, see: Sloopa et al., 2002)
The ligand 4,4,4-trifluoro-1-(4-methoxyphenyl)-2-butene-1,3-dione was synthesized according to the reported literature (Sloopa et al., 2002). The coordination compound was prepared as follows: The ligand (0.344 g, 1.4 mmol) and pyridine (0.111 g, 1.4 mmol) in 20 ml hot acetone was added slowly to the Co(CH3COO)2·4H2O (0.174 g, 0.7 mmol) solution of 10 ml water. The mixture was stirred for 3 h. After filtration, the red solution was allowed to stand at room temperature. Red block-shaped crystals suitable for X-ray analysis were obtained in several days.
All the H atoms were placed at their idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker (2001); software used to prepare material for publication: SHELXTL (Bruker (2001).
[Co(C11H8F3O3)2(C5H5N)2] | Z = 1 |
Mr = 707.48 | F(000) = 361 |
Triclinic, P1 | Dx = 1.502 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3199 (10) Å | Cell parameters from 1762 reflections |
b = 10.2375 (15) Å | θ = 2.3–23.8° |
c = 11.9968 (17) Å | µ = 0.63 mm−1 |
α = 66.641 (2)° | T = 295 K |
β = 84.821 (2)° | Plate, red |
γ = 71.477 (2)° | 0.20 × 0.20 × 0.10 mm |
V = 781.91 (19) Å3 |
Bruker SMART 4K CCD area-detector diffractometer | 3027 independent reflections |
Radiation source: fine-focus sealed tube | 2326 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
ϕ and ω scans | θmax = 26.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −8→8 |
Tmin = 0.866, Tmax = 0.940 | k = −11→12 |
5023 measured reflections | l = −14→14 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0597P)2] where P = (Fo2 + 2Fc2)/3 |
3027 reflections | (Δ/σ)max < 0.001 |
215 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
[Co(C11H8F3O3)2(C5H5N)2] | γ = 71.477 (2)° |
Mr = 707.48 | V = 781.91 (19) Å3 |
Triclinic, P1 | Z = 1 |
a = 7.3199 (10) Å | Mo Kα radiation |
b = 10.2375 (15) Å | µ = 0.63 mm−1 |
c = 11.9968 (17) Å | T = 295 K |
α = 66.641 (2)° | 0.20 × 0.20 × 0.10 mm |
β = 84.821 (2)° |
Bruker SMART 4K CCD area-detector diffractometer | 3027 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 2326 reflections with I > 2σ(I) |
Tmin = 0.866, Tmax = 0.940 | Rint = 0.045 |
5023 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.54 e Å−3 |
3027 reflections | Δρmin = −0.31 e Å−3 |
215 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | −0.3653 (4) | 0.6315 (4) | −0.0412 (3) | 0.0843 (10) | |
H1A | −0.2862 | 0.5297 | −0.0206 | 0.126* | |
H1B | −0.4541 | 0.6601 | −0.1071 | 0.126* | |
H1C | −0.4359 | 0.6409 | 0.0282 | 0.126* | |
C2 | −0.1157 (4) | 0.7072 (3) | 0.0068 (2) | 0.0542 (6) | |
C3 | −0.0098 (4) | 0.8064 (3) | −0.0296 (2) | 0.0579 (7) | |
H3 | −0.0317 | 0.8812 | −0.1073 | 0.069* | |
C4 | 0.1267 (4) | 0.7967 (3) | 0.0468 (2) | 0.0509 (6) | |
H4 | 0.1958 | 0.8650 | 0.0201 | 0.061* | |
C5 | 0.1635 (3) | 0.6863 (3) | 0.16331 (19) | 0.0427 (5) | |
C6 | 0.0564 (4) | 0.5885 (3) | 0.1974 (2) | 0.0569 (7) | |
H6 | 0.0790 | 0.5131 | 0.2749 | 0.068* | |
C7 | −0.0828 (4) | 0.5970 (3) | 0.1223 (2) | 0.0605 (7) | |
H7 | −0.1531 | 0.5295 | 0.1491 | 0.073* | |
C8 | 0.3086 (3) | 0.6684 (3) | 0.2516 (2) | 0.0447 (6) | |
C9 | 0.4020 (4) | 0.7779 (3) | 0.2259 (2) | 0.0523 (6) | |
H9 | 0.3685 | 0.8606 | 0.1528 | 0.063* | |
C10 | 0.5388 (3) | 0.7713 (3) | 0.3010 (2) | 0.0469 (6) | |
C11 | 0.6189 (4) | 0.9035 (3) | 0.2584 (2) | 0.0579 (7) | |
C12 | 0.2994 (5) | 0.7244 (4) | 0.6183 (3) | 0.0737 (8) | |
H12 | 0.4270 | 0.7102 | 0.6363 | 0.088* | |
C13 | 0.1576 (6) | 0.8161 (4) | 0.6588 (3) | 0.0904 (10) | |
H13 | 0.1888 | 0.8618 | 0.7044 | 0.108* | |
C14 | −0.0307 (5) | 0.8407 (4) | 0.6321 (3) | 0.0876 (10) | |
H14 | −0.1299 | 0.9036 | 0.6585 | 0.105* | |
C15 | −0.0693 (5) | 0.7698 (4) | 0.5654 (3) | 0.0795 (9) | |
H15 | −0.1959 | 0.7841 | 0.5454 | 0.095* | |
C16 | 0.0803 (5) | 0.6780 (3) | 0.5285 (2) | 0.0702 (8) | |
H16 | 0.0521 | 0.6303 | 0.4835 | 0.084* | |
Co | 0.5000 | 0.5000 | 0.5000 | 0.0551 (2) | |
F1 | 0.5934 (3) | 0.9857 (2) | 0.13895 (16) | 0.0954 (6) | |
F2 | 0.8062 (2) | 0.86269 (19) | 0.28260 (16) | 0.0767 (5) | |
F3 | 0.5351 (3) | 0.9960 (2) | 0.3128 (2) | 0.0957 (6) | |
N | 0.2648 (3) | 0.6535 (2) | 0.55390 (18) | 0.0608 (6) | |
O1 | −0.2461 (3) | 0.7266 (2) | −0.07681 (18) | 0.0753 (6) | |
O2 | 0.3404 (3) | 0.55291 (19) | 0.34842 (14) | 0.0601 (5) | |
O3 | 0.6076 (3) | 0.67465 (19) | 0.40365 (14) | 0.0590 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0606 (19) | 0.105 (3) | 0.109 (3) | −0.0285 (19) | −0.0118 (16) | −0.058 (2) |
C2 | 0.0478 (15) | 0.0556 (16) | 0.0588 (16) | −0.0093 (13) | −0.0077 (12) | −0.0250 (13) |
C3 | 0.0676 (17) | 0.0510 (16) | 0.0460 (14) | −0.0186 (14) | −0.0099 (12) | −0.0070 (12) |
C4 | 0.0566 (15) | 0.0470 (14) | 0.0459 (13) | −0.0210 (12) | −0.0008 (11) | −0.0102 (11) |
C5 | 0.0452 (13) | 0.0414 (13) | 0.0413 (12) | −0.0148 (11) | 0.0017 (10) | −0.0147 (10) |
C6 | 0.0664 (17) | 0.0542 (16) | 0.0476 (14) | −0.0300 (14) | −0.0048 (12) | −0.0071 (12) |
C7 | 0.0607 (17) | 0.0616 (17) | 0.0644 (17) | −0.0313 (14) | −0.0010 (13) | −0.0196 (14) |
C8 | 0.0518 (14) | 0.0433 (14) | 0.0388 (12) | −0.0180 (11) | 0.0016 (10) | −0.0133 (11) |
C9 | 0.0586 (15) | 0.0467 (14) | 0.0486 (14) | −0.0225 (12) | −0.0051 (11) | −0.0090 (11) |
C10 | 0.0499 (14) | 0.0419 (14) | 0.0501 (14) | −0.0194 (11) | 0.0045 (11) | −0.0157 (12) |
C11 | 0.0579 (17) | 0.0478 (15) | 0.0644 (17) | −0.0232 (13) | −0.0014 (13) | −0.0121 (13) |
C12 | 0.077 (2) | 0.081 (2) | 0.081 (2) | −0.0419 (18) | 0.0028 (16) | −0.0355 (18) |
C13 | 0.102 (3) | 0.097 (3) | 0.103 (3) | −0.051 (2) | 0.020 (2) | −0.059 (2) |
C14 | 0.088 (3) | 0.083 (2) | 0.090 (2) | −0.030 (2) | 0.0171 (19) | −0.032 (2) |
C15 | 0.071 (2) | 0.090 (2) | 0.0695 (19) | −0.033 (2) | 0.0002 (16) | −0.0151 (18) |
C16 | 0.082 (2) | 0.071 (2) | 0.0597 (17) | −0.0391 (18) | −0.0038 (15) | −0.0146 (15) |
Co | 0.0734 (4) | 0.0517 (3) | 0.0401 (3) | −0.0326 (3) | −0.0113 (2) | −0.0045 (2) |
F1 | 0.1143 (15) | 0.0826 (13) | 0.0786 (12) | −0.0660 (12) | −0.0169 (10) | 0.0115 (10) |
F2 | 0.0534 (10) | 0.0692 (11) | 0.1055 (12) | −0.0299 (8) | −0.0028 (8) | −0.0223 (9) |
F3 | 0.0876 (13) | 0.0705 (12) | 0.1550 (18) | −0.0335 (10) | 0.0235 (12) | −0.0668 (13) |
N | 0.0734 (16) | 0.0577 (14) | 0.0544 (12) | −0.0338 (12) | −0.0040 (11) | −0.0129 (11) |
O1 | 0.0648 (12) | 0.0808 (14) | 0.0792 (13) | −0.0190 (11) | −0.0264 (10) | −0.0268 (11) |
O2 | 0.0833 (13) | 0.0539 (11) | 0.0436 (9) | −0.0371 (10) | −0.0132 (8) | −0.0036 (8) |
O3 | 0.0740 (12) | 0.0568 (11) | 0.0474 (10) | −0.0340 (10) | −0.0108 (8) | −0.0080 (9) |
C1—O1 | 1.426 (4) | C10—C11 | 1.529 (3) |
C1—H1A | 0.9600 | C11—F3 | 1.322 (3) |
C1—H1B | 0.9600 | C11—F2 | 1.323 (3) |
C1—H1C | 0.9600 | C11—F1 | 1.337 (3) |
C2—O1 | 1.360 (3) | C12—N | 1.335 (4) |
C2—C7 | 1.378 (4) | C12—C13 | 1.359 (4) |
C2—C3 | 1.382 (4) | C12—H12 | 0.9300 |
C3—C4 | 1.370 (3) | C13—C14 | 1.364 (5) |
C3—H3 | 0.9300 | C13—H13 | 0.9300 |
C4—C5 | 1.388 (3) | C14—C15 | 1.370 (5) |
C4—H4 | 0.9300 | C14—H14 | 0.9300 |
C5—C6 | 1.379 (3) | C15—C16 | 1.367 (4) |
C5—C8 | 1.486 (3) | C15—H15 | 0.9300 |
C6—C7 | 1.381 (3) | C16—N | 1.334 (3) |
C6—H6 | 0.9300 | C16—H16 | 0.9300 |
C7—H7 | 0.9300 | Co—O2 | 2.0408 (15) |
C8—O2 | 1.259 (3) | Co—O2i | 2.0408 (15) |
C8—C9 | 1.412 (3) | Co—O3i | 2.0603 (17) |
C9—C10 | 1.374 (3) | Co—O3 | 2.0603 (17) |
C9—H9 | 0.9300 | Co—Ni | 2.177 (2) |
C10—O3 | 1.257 (3) | Co—N | 2.177 (2) |
O1—C1—H1A | 109.5 | F1—C11—C10 | 114.0 (2) |
O1—C1—H1B | 109.5 | N—C12—C13 | 123.3 (3) |
H1A—C1—H1B | 109.5 | N—C12—H12 | 118.4 |
O1—C1—H1C | 109.5 | C13—C12—H12 | 118.4 |
H1A—C1—H1C | 109.5 | C12—C13—C14 | 119.6 (3) |
H1B—C1—H1C | 109.5 | C12—C13—H13 | 120.2 |
O1—C2—C7 | 124.8 (2) | C14—C13—H13 | 120.2 |
O1—C2—C3 | 116.2 (2) | C13—C14—C15 | 118.0 (3) |
C7—C2—C3 | 119.0 (2) | C13—C14—H14 | 121.0 |
C4—C3—C2 | 121.3 (2) | C15—C14—H14 | 121.0 |
C4—C3—H3 | 119.4 | C16—C15—C14 | 119.3 (3) |
C2—C3—H3 | 119.4 | C16—C15—H15 | 120.3 |
C3—C4—C5 | 121.0 (2) | C14—C15—H15 | 120.3 |
C3—C4—H4 | 119.5 | N—C16—C15 | 123.1 (3) |
C5—C4—H4 | 119.5 | N—C16—H16 | 118.5 |
C6—C5—C4 | 116.7 (2) | C15—C16—H16 | 118.5 |
C6—C5—C8 | 119.0 (2) | O2—Co—O2i | 179.999 (1) |
C4—C5—C8 | 124.3 (2) | O2—Co—O3i | 91.06 (6) |
C5—C6—C7 | 123.2 (2) | O2i—Co—O3i | 88.94 (6) |
C5—C6—H6 | 118.4 | O2—Co—O3 | 88.94 (6) |
C7—C6—H6 | 118.4 | O2i—Co—O3 | 91.06 (6) |
C2—C7—C6 | 118.8 (2) | O3i—Co—O3 | 180.000 (1) |
C2—C7—H7 | 120.6 | O2—Co—Ni | 90.34 (8) |
C6—C7—H7 | 120.6 | O2i—Co—Ni | 89.66 (8) |
O2—C8—C9 | 123.1 (2) | O3i—Co—Ni | 88.90 (8) |
O2—C8—C5 | 116.5 (2) | O3—Co—Ni | 91.10 (8) |
C9—C8—C5 | 120.4 (2) | O2—Co—N | 89.66 (8) |
C10—C9—C8 | 124.9 (2) | O2i—Co—N | 90.34 (8) |
C10—C9—H9 | 117.6 | O3i—Co—N | 91.10 (8) |
C8—C9—H9 | 117.6 | O3—Co—N | 88.90 (8) |
O3—C10—C9 | 130.4 (2) | Ni—Co—N | 179.998 (2) |
O3—C10—C11 | 112.6 (2) | C16—N—C12 | 116.7 (3) |
C9—C10—C11 | 116.9 (2) | C16—N—Co | 122.3 (2) |
F3—C11—F2 | 106.2 (2) | C12—N—Co | 121.0 (2) |
F3—C11—F1 | 106.3 (2) | C2—O1—C1 | 118.1 (2) |
F2—C11—F1 | 105.7 (2) | C8—O2—Co | 128.63 (15) |
F3—C11—C10 | 110.9 (2) | C10—O3—Co | 122.64 (15) |
F2—C11—C10 | 113.1 (2) | ||
O1—C2—C3—C4 | −179.5 (2) | C14—C15—C16—N | −0.3 (5) |
C7—C2—C3—C4 | 0.2 (4) | C15—C16—N—C12 | −0.2 (4) |
C2—C3—C4—C5 | 0.1 (4) | C15—C16—N—Co | 177.6 (2) |
C3—C4—C5—C6 | 0.0 (4) | C13—C12—N—C16 | 0.8 (4) |
C3—C4—C5—C8 | −179.9 (2) | C13—C12—N—Co | −177.0 (2) |
C4—C5—C6—C7 | −0.5 (4) | O2—Co—N—C16 | 32.4 (2) |
C8—C5—C6—C7 | 179.4 (2) | O2i—Co—N—C16 | −147.6 (2) |
O1—C2—C7—C6 | 179.0 (2) | O3i—Co—N—C16 | −58.6 (2) |
C3—C2—C7—C6 | −0.6 (4) | O3—Co—N—C16 | 121.4 (2) |
C5—C6—C7—C2 | 0.8 (4) | O2—Co—N—C12 | −149.9 (2) |
C6—C5—C8—O2 | 8.0 (3) | O2i—Co—N—C12 | 30.1 (2) |
C4—C5—C8—O2 | −172.1 (2) | O3i—Co—N—C12 | 119.0 (2) |
C6—C5—C8—C9 | −171.5 (2) | O3—Co—N—C12 | −61.0 (2) |
C4—C5—C8—C9 | 8.4 (4) | C7—C2—O1—C1 | 3.5 (4) |
O2—C8—C9—C10 | 1.0 (4) | C3—C2—O1—C1 | −176.9 (2) |
C5—C8—C9—C10 | −179.5 (2) | C9—C8—O2—Co | 8.0 (4) |
C8—C9—C10—O3 | −0.9 (4) | C5—C8—O2—Co | −171.42 (15) |
C8—C9—C10—C11 | −178.3 (2) | O3i—Co—O2—C8 | 168.1 (2) |
O3—C10—C11—F3 | −78.0 (3) | O3—Co—O2—C8 | −11.9 (2) |
C9—C10—C11—F3 | 99.9 (3) | Ni—Co—O2—C8 | −103.0 (2) |
O3—C10—C11—F2 | 41.2 (3) | N—C1—O2—C8 | −94.49 (19) |
C9—C10—C11—F2 | −140.9 (2) | C9—C10—O3—Co | −7.6 (4) |
O3—C10—C11—F1 | 162.1 (2) | C11—C10—O3—Co | 169.87 (16) |
C9—C10—C11—F1 | −20.1 (3) | O2—Co—O3—C10 | 11.02 (19) |
N—C12—C13—C14 | −1.0 (5) | O2i—Co—O3—C10 | −168.98 (19) |
C12—C13—C14—C15 | 0.5 (5) | Ni—Co—O3—C10 | 101.3 (2) |
C13—C14—C15—C16 | 0.1 (5) | N—Co—O3—C10 | −78.7 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···Cgii | 0.93 | 3.22 | 3.884 (3) | 131 |
Symmetry code: (ii) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Co(C11H8F3O3)2(C5H5N)2] |
Mr | 707.48 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 7.3199 (10), 10.2375 (15), 11.9968 (17) |
α, β, γ (°) | 66.641 (2), 84.821 (2), 71.477 (2) |
V (Å3) | 781.91 (19) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.63 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 4K CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.866, 0.940 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5023, 3027, 2326 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.117, 0.97 |
No. of reflections | 3027 |
No. of parameters | 215 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.54, −0.31 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker (2001).
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···Cgi | 0.93 | 3.22 | 3.884 (3) | 130.5 |
Symmetry code: (i) −x, −y+1, −z+1. |
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Coordination complexes of divalent transition metal ions with β-diketonate ligands have proven useful in a wide range of applications (Soldatov et al., 2003).
In the title compound, the coordination of the CoII centre (Fig. 1) is distorted octahedral, with the O donor atoms of the β-diketonate ligand occupying equatorial positions and N atoms of two pyridine ligands in the axial positions. Co cation shows positive bivalence, and β-diketones show negative bivalence after loss of two hydrogen protons. The molecular packing (Fig. 2) is stabilized by weak C—H···π interactions between the benzene-H atom and the neighboring pyridine ring unit, with a C6—H6···Cgi separation of 3.22 Å (Fig. 2 & Table 1) (Cg is the centroid of C2—C7 benzene ring, symmetry code as in Fig. 2).