In the title compound, [Co(C
8H
8NO
2)
2], the Co atom has a distorted square-planar coordination involving two N atoms and two O atoms from two ethanone 1-(2-hydroxyphenyl)oximato ligands. The molecular structure and packing are stabilized by intramolecular O—H
O hydrogen bonds and C—H
π intermolecular interaction.
Supporting information
CCDC reference: 613805
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.042
- wR factor = 0.130
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Co1 - N1 .. 6.24 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Co1 - N2 .. 5.71 su
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
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).
trans-Bis[ethanone 1-(2-hydroxyphenyl)oximato]cobalt(II)
top
Crystal data top
[Co(C8H8NO2)2] | F(000) = 740 |
Mr = 359.24 | Dx = 1.592 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 7.8420 (16) Å | θ = 4–14° |
b = 9.913 (2) Å | µ = 1.17 mm−1 |
c = 19.344 (4) Å | T = 295 K |
β = 94.43 (3)° | Block, blue |
V = 1499.3 (5) Å3 | 0.25 × 0.20 × 0.18 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.068 |
Radiation source: fine-focus sealed tube | θmax = 27.0°, θmin = 2.1° |
Graphite monochromator | h = 0→10 |
ω scans | k = 0→12 |
3496 measured reflections | l = −24→24 |
3257 independent reflections | 3 standard reflections every 100 reflections |
2614 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0702P)2 + 1.1322P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
3257 reflections | Δρmax = 0.94 e Å−3 |
219 parameters | Δρmin = −0.79 e Å−3 |
2 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0049 (10) |
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 | |
Co1 | 0.53882 (4) | 0.60254 (4) | 0.084996 (19) | 0.03543 (16) | |
O1 | 0.7078 (3) | 0.5747 (2) | 0.15351 (13) | 0.0529 (6) | |
O2 | 0.2285 (3) | 0.4675 (3) | 0.09144 (14) | 0.0572 (6) | |
O3 | 0.3691 (3) | 0.6332 (3) | 0.01735 (13) | 0.0546 (6) | |
O4 | 0.8512 (3) | 0.7326 (3) | 0.07762 (15) | 0.0682 (8) | |
N1 | 0.3914 (3) | 0.4796 (3) | 0.12570 (13) | 0.0428 (6) | |
N2 | 0.6849 (3) | 0.7286 (3) | 0.04622 (14) | 0.0447 (6) | |
C1 | 0.2732 (4) | 0.3124 (4) | 0.1989 (2) | 0.0595 (9) | |
H1A | 0.1685 | 0.3384 | 0.1734 | 0.089* | |
H1B | 0.2601 | 0.3196 | 0.2477 | 0.089* | |
H1C | 0.3002 | 0.2208 | 0.1878 | 0.089* | |
C2 | 0.4149 (4) | 0.4032 (3) | 0.17998 (16) | 0.0421 (6) | |
C3 | 0.5785 (4) | 0.4049 (3) | 0.22093 (16) | 0.0430 (7) | |
C4 | 0.6044 (5) | 0.3170 (4) | 0.27821 (19) | 0.0570 (8) | |
H4B | 0.5164 | 0.2592 | 0.2885 | 0.068* | |
C5 | 0.7561 (5) | 0.3139 (4) | 0.3194 (2) | 0.0636 (10) | |
H5A | 0.7692 | 0.2557 | 0.3572 | 0.076* | |
C6 | 0.8884 (5) | 0.3984 (4) | 0.30396 (19) | 0.0561 (8) | |
H6A | 0.9911 | 0.3973 | 0.3314 | 0.067* | |
C7 | 0.8680 (4) | 0.4838 (3) | 0.24800 (18) | 0.0504 (7) | |
H7A | 0.9581 | 0.5394 | 0.2377 | 0.060* | |
C8 | 0.7150 (4) | 0.4885 (3) | 0.20650 (16) | 0.0439 (7) | |
C9 | 0.7998 (4) | 0.9055 (4) | −0.0221 (2) | 0.0562 (9) | |
H9A | 0.9047 | 0.8782 | 0.0028 | 0.084* | |
H9B | 0.7732 | 0.9965 | −0.0096 | 0.084* | |
H9C | 0.8122 | 0.9009 | −0.0710 | 0.084* | |
C10 | 0.6585 (4) | 0.8138 (3) | −0.00410 (16) | 0.0419 (6) | |
C11 | 0.4918 (4) | 0.8169 (3) | −0.04317 (16) | 0.0413 (6) | |
C12 | 0.4633 (4) | 0.9121 (3) | −0.09765 (18) | 0.0519 (8) | |
H12A | 0.5489 | 0.9738 | −0.1057 | 0.062* | |
C13 | 0.3127 (5) | 0.9154 (4) | −0.1386 (2) | 0.0602 (9) | |
H13A | 0.2971 | 0.9784 | −0.1741 | 0.072* | |
C14 | 0.1845 (4) | 0.8252 (4) | −0.12697 (19) | 0.0568 (9) | |
H14A | 0.0826 | 0.8271 | −0.1550 | 0.068* | |
C15 | 0.2061 (4) | 0.7324 (3) | −0.07427 (17) | 0.0494 (7) | |
H15A | 0.1180 | 0.6727 | −0.0666 | 0.059* | |
C16 | 0.3588 (4) | 0.7267 (3) | −0.03200 (16) | 0.0431 (6) | |
H2A | 0.232 (6) | 0.528 (4) | 0.0598 (18) | 0.087 (15)* | |
H4A | 0.849 (8) | 0.676 (5) | 0.111 (2) | 0.13 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0367 (2) | 0.0323 (2) | 0.0370 (2) | −0.00558 (15) | 0.00037 (15) | −0.00015 (15) |
O1 | 0.0483 (12) | 0.0531 (13) | 0.0554 (14) | −0.0138 (10) | −0.0084 (10) | 0.0125 (11) |
O2 | 0.0475 (12) | 0.0638 (16) | 0.0589 (15) | −0.0174 (12) | −0.0053 (10) | 0.0095 (13) |
O3 | 0.0473 (12) | 0.0543 (13) | 0.0602 (15) | −0.0136 (10) | −0.0083 (10) | 0.0149 (11) |
O4 | 0.0473 (13) | 0.0808 (19) | 0.0734 (18) | −0.0243 (13) | −0.0143 (12) | 0.0219 (15) |
N1 | 0.0402 (12) | 0.0410 (13) | 0.0469 (14) | −0.0063 (10) | 0.0021 (10) | −0.0044 (11) |
N2 | 0.0417 (13) | 0.0455 (14) | 0.0463 (14) | −0.0092 (11) | −0.0011 (10) | −0.0011 (11) |
C1 | 0.0561 (19) | 0.060 (2) | 0.063 (2) | −0.0156 (17) | 0.0110 (16) | 0.0061 (18) |
C2 | 0.0462 (15) | 0.0373 (15) | 0.0439 (16) | −0.0023 (12) | 0.0106 (12) | −0.0027 (13) |
C3 | 0.0473 (16) | 0.0392 (15) | 0.0432 (16) | 0.0018 (12) | 0.0086 (12) | −0.0007 (12) |
C4 | 0.0592 (19) | 0.056 (2) | 0.056 (2) | −0.0024 (16) | 0.0096 (16) | 0.0143 (16) |
C5 | 0.069 (2) | 0.063 (2) | 0.058 (2) | 0.0047 (19) | 0.0021 (17) | 0.0159 (18) |
C6 | 0.0592 (19) | 0.056 (2) | 0.0512 (19) | 0.0060 (16) | −0.0060 (15) | 0.0033 (16) |
C7 | 0.0495 (17) | 0.0474 (17) | 0.0534 (19) | −0.0018 (14) | −0.0014 (14) | 0.0007 (15) |
C8 | 0.0498 (16) | 0.0357 (14) | 0.0460 (17) | 0.0000 (13) | 0.0035 (13) | −0.0039 (12) |
C9 | 0.0511 (18) | 0.056 (2) | 0.063 (2) | −0.0128 (15) | 0.0092 (15) | 0.0081 (16) |
C10 | 0.0461 (15) | 0.0366 (14) | 0.0443 (16) | −0.0033 (12) | 0.0110 (12) | −0.0034 (12) |
C11 | 0.0460 (15) | 0.0368 (14) | 0.0420 (16) | 0.0013 (12) | 0.0099 (12) | −0.0041 (12) |
C12 | 0.058 (2) | 0.0460 (18) | 0.0531 (19) | −0.0010 (14) | 0.0113 (15) | 0.0065 (14) |
C13 | 0.063 (2) | 0.060 (2) | 0.058 (2) | 0.0078 (17) | 0.0066 (17) | 0.0187 (17) |
C14 | 0.0520 (18) | 0.065 (2) | 0.052 (2) | 0.0080 (17) | −0.0038 (15) | 0.0057 (16) |
C15 | 0.0464 (16) | 0.0480 (17) | 0.0534 (19) | −0.0002 (14) | 0.0018 (13) | −0.0012 (15) |
C16 | 0.0468 (15) | 0.0400 (15) | 0.0427 (16) | 0.0015 (12) | 0.0053 (12) | −0.0037 (12) |
Geometric parameters (Å, º) top
Co1—O3 | 1.819 (2) | C5—C6 | 1.384 (5) |
Co1—O1 | 1.821 (2) | C5—H5A | 0.9300 |
Co1—N2 | 1.889 (3) | C6—C7 | 1.374 (5) |
Co1—N1 | 1.892 (3) | C6—H6A | 0.9300 |
O1—C8 | 1.333 (4) | C7—C8 | 1.392 (4) |
O2—N1 | 1.398 (3) | C7—H7A | 0.9300 |
O2—H2A | 0.86 (4) | C9—C10 | 1.495 (4) |
O3—C16 | 1.328 (4) | C9—H9A | 0.9600 |
O4—N2 | 1.396 (3) | C9—H9B | 0.9600 |
O4—H4A | 0.86 (4) | C9—H9C | 0.9600 |
N1—C2 | 1.296 (4) | C10—C11 | 1.459 (4) |
N2—C10 | 1.293 (4) | C11—C16 | 1.403 (4) |
C1—C2 | 1.498 (4) | C11—C12 | 1.420 (4) |
C1—H1A | 0.9600 | C12—C13 | 1.371 (5) |
C1—H1B | 0.9600 | C12—H12A | 0.9300 |
C1—H1C | 0.9600 | C13—C14 | 1.377 (5) |
C2—C3 | 1.455 (4) | C13—H13A | 0.9300 |
C3—C8 | 1.399 (4) | C14—C15 | 1.373 (5) |
C3—C4 | 1.412 (5) | C14—H14A | 0.9300 |
C4—C5 | 1.380 (5) | C15—C16 | 1.399 (4) |
C4—H4B | 0.9300 | C15—H15A | 0.9300 |
| | | |
O3—Co1—O1 | 178.95 (12) | C7—C6—H6A | 120.0 |
O3—Co1—N2 | 92.07 (11) | C5—C6—H6A | 120.0 |
O1—Co1—N2 | 87.69 (11) | C6—C7—C8 | 121.2 (3) |
O3—Co1—N1 | 88.31 (11) | C6—C7—H7A | 119.4 |
O1—Co1—N1 | 91.91 (11) | C8—C7—H7A | 119.4 |
N2—Co1—N1 | 178.49 (11) | O1—C8—C7 | 116.6 (3) |
C8—O1—Co1 | 129.9 (2) | O1—C8—C3 | 123.1 (3) |
N1—O2—H2A | 101 (3) | C7—C8—C3 | 120.3 (3) |
C16—O3—Co1 | 129.4 (2) | C10—C9—H9A | 109.5 |
N2—O4—H4A | 104 (4) | C10—C9—H9B | 109.5 |
C2—N1—O2 | 113.7 (2) | H9A—C9—H9B | 109.5 |
C2—N1—Co1 | 131.3 (2) | C10—C9—H9C | 109.5 |
O2—N1—Co1 | 115.04 (19) | H9A—C9—H9C | 109.5 |
C10—N2—O4 | 113.5 (3) | H9B—C9—H9C | 109.5 |
C10—N2—Co1 | 131.6 (2) | N2—C10—C11 | 119.2 (3) |
O4—N2—Co1 | 114.9 (2) | N2—C10—C9 | 119.6 (3) |
C2—C1—H1A | 109.5 | C11—C10—C9 | 121.2 (3) |
C2—C1—H1B | 109.5 | C16—C11—C12 | 117.5 (3) |
H1A—C1—H1B | 109.5 | C16—C11—C10 | 123.6 (3) |
C2—C1—H1C | 109.5 | C12—C11—C10 | 118.8 (3) |
H1A—C1—H1C | 109.5 | C13—C12—C11 | 121.6 (3) |
H1B—C1—H1C | 109.5 | C13—C12—H12A | 119.2 |
N1—C2—C3 | 119.9 (3) | C11—C12—H12A | 119.2 |
N1—C2—C1 | 119.2 (3) | C12—C13—C14 | 119.8 (3) |
C3—C2—C1 | 120.9 (3) | C12—C13—H13A | 120.1 |
C8—C3—C4 | 117.1 (3) | C14—C13—H13A | 120.1 |
C8—C3—C2 | 123.7 (3) | C15—C14—C13 | 120.4 (3) |
C4—C3—C2 | 119.2 (3) | C15—C14—H14A | 119.8 |
C5—C4—C3 | 122.2 (3) | C13—C14—H14A | 119.8 |
C5—C4—H4B | 118.9 | C14—C15—C16 | 120.8 (3) |
C3—C4—H4B | 118.9 | C14—C15—H15A | 119.6 |
C4—C5—C6 | 119.2 (3) | C16—C15—H15A | 119.6 |
C4—C5—H5A | 120.4 | O3—C16—C15 | 116.8 (3) |
C6—C5—H5A | 120.4 | O3—C16—C11 | 123.4 (3) |
C7—C6—C5 | 120.0 (3) | C15—C16—C11 | 119.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O3 | 0.86 (4) | 1.75 (3) | 2.493 (3) | 144 (4) |
O4—H4A···O1 | 0.86 (4) | 1.75 (4) | 2.475 (4) | 141 (6) |