Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045163/dn2225sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045163/dn2225Isup2.hkl |
CCDC reference: 663640
Key indicators
- Single-crystal X-ray study
- T = 423 K
- Mean (C-C) = 0.007 Å
- Disorder in main residue
- R factor = 0.060
- wR factor = 0.170
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for P3
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.27 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.69 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Co1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for P2 PLAT301_ALERT_3_C Main Residue Disorder ......................... 13.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C1 - C2 ... 1.39 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C8 - C9 ... 1.38 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C8 - C13 ... 1.37 Ang. PLAT410_ALERT_2_C Short Intra H...H Contact H6A .. H13 .. 1.91 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 12 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 3.00 Deg. C7B -C2 -C7A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 9.60 Deg. C4A -C3 -C4B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 28.10 Deg. C6A -C8 -C6B 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 11
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Standard vacuum techniques were used in manipulations of volatile and air-sensitive material. 2-Hydroxy-5-phenyl-cyclohex-1-enecarbaldehyde (958 mg, 4.74 mmol) in diethyl ether (20 mL) was combined with [CoMe3(PMe3)3] (1,810 mg, 5.45 mmol) in diethyl ether(40 ml) at room temperature. The mixture was stirred for 20 h. During this period the solution turned red. The volatiles were removed in vacuo and the residue was extracted with pentane. Crystallization at -20 °C afforded red microcrystals.
All H atoms were fixed geometrically and treated as riding on their parent atoms with C—H = 0.93Å (aromatic), 0.96Å (methyl), 0.97Å (methylene) and 0.98Å (methine) with Uiso(H) = xUeq(C), x having the value 1.2 or 1.5(methylene).
The cyclohexene is partially stastically distributed over two positions. This disordered moiety was treated using the restraints available in SHELXL97 (SAME and PART instructions). The value of the occupancy factor, 1/2, was determined in the first stages of the refinement. The thermal displacement parameters for the disordered atoms were restrained using equal Uij constraint.
Reaction of substituted enolated malonic dialdehydes (enol-form: b-keton-aldehyde) with [CoMe3(PMe3)3] was recently reported (Li et al., 2005). 2-Hydroxy-5-phenyl-cyclohex-1-enecarbaldehyde reacts with [CoMe3(PMe3)3] (Scheme) by elimination of methane and trimethylphosphine utilizing both the phenolato and the keto-oxygen functions to afford the hexacoordinate title cobalt(III) complex as red solids that are soluble in pentane or diethyl ether. Single crystals suitable for X-ray diffraction analysis of title compound were obtained.
A view of the molecular structure is given in Figure 1. Cobalt atom displays an octahedral coordination with two equatorial cis-methyl groups (C20 and C21) and two axial trimethylphosphines as well as a bidentate ligand. The angle P1–Co–P2 of 174.59 (5) implies a slight distortion from an ideal octahedron. The substituted salicylaldehyde ligands have Co—O bond lengths of Co1—O1 1.987 (2), Co1—O2 1.980 (3). The chelate ring is planar with the largest deviation from the plane being 0.030 (3)Å at O2.
For related literature, see: Li et al. (2005).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).
[Co(CH3)2(C13H13O2)(C3H9P)2] | F(000) = 944 |
Mr = 442.38 | Dx = 1.199 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4681 reflections |
a = 14.109 (3) Å | θ = 2.3–24.3° |
b = 9.2740 (19) Å | µ = 0.84 mm−1 |
c = 19.577 (4) Å | T = 423 K |
β = 106.94 (3)° | Block, red |
V = 2450.4 (10) Å3 | 0.32 × 0.20 × 0.12 mm |
Z = 4 |
CCD area-detector diffractometer | 4287 independent reflections |
Radiation source: fine-focus sealed tube | 3853 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
φ and ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→16 |
Tmin = 0.774, Tmax = 0.906 | k = −10→11 |
15313 measured reflections | l = −23→23 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.171 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0921P)2 + 3.5216P] where P = (Fo2 + 2Fc2)/3 |
4287 reflections | (Δ/σ)max = 0.008 |
249 parameters | Δρmax = 1.68 e Å−3 |
11 restraints | Δρmin = −0.85 e Å−3 |
[Co(CH3)2(C13H13O2)(C3H9P)2] | V = 2450.4 (10) Å3 |
Mr = 442.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.109 (3) Å | µ = 0.84 mm−1 |
b = 9.2740 (19) Å | T = 423 K |
c = 19.577 (4) Å | 0.32 × 0.20 × 0.12 mm |
β = 106.94 (3)° |
CCD area-detector diffractometer | 4287 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3853 reflections with I > 2σ(I) |
Tmin = 0.774, Tmax = 0.906 | Rint = 0.056 |
15313 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 11 restraints |
wR(F2) = 0.171 | H-atom parameters constrained |
S = 1.05 | Δρmax = 1.68 e Å−3 |
4287 reflections | Δρmin = −0.85 e Å−3 |
249 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 | Occ. (<1) | |
C1 | 0.3655 (3) | 0.6037 (5) | 0.2286 (2) | 0.0656 (13) | |
H1 | 0.4182 | 0.5404 | 0.2333 | 0.079* | |
C2 | 0.3761 (3) | 0.7006 (4) | 0.2847 (2) | 0.0507 (9) | |
C3 | 0.3028 (3) | 0.8021 (4) | 0.28556 (19) | 0.0443 (8) | |
C4A | 0.3159 (10) | 0.8974 (17) | 0.3510 (6) | 0.0588 (14) | 0.50 |
H4A1 | 0.2780 | 0.8565 | 0.3805 | 0.071* | 0.50 |
H4A2 | 0.2884 | 0.9918 | 0.3354 | 0.071* | 0.50 |
C5A | 0.4261 (6) | 0.9165 (10) | 0.3979 (5) | 0.0588 (14) | 0.50 |
H5A1 | 0.4636 | 0.9709 | 0.3723 | 0.071* | 0.50 |
H5A2 | 0.4291 | 0.9667 | 0.4419 | 0.071* | 0.50 |
C6A | 0.4676 (7) | 0.7631 (11) | 0.4136 (5) | 0.050 (2) | 0.50 |
H6A | 0.4249 | 0.7052 | 0.4344 | 0.059* | 0.50 |
C7A | 0.4736 (15) | 0.696 (3) | 0.3447 (11) | 0.0588 (14) | 0.50 |
H7A1 | 0.4941 | 0.5962 | 0.3537 | 0.071* | 0.50 |
H7A2 | 0.5240 | 0.7458 | 0.3290 | 0.071* | 0.50 |
C4B | 0.3213 (10) | 0.9155 (16) | 0.3432 (6) | 0.0588 (14) | 0.50 |
H4B1 | 0.2593 | 0.9388 | 0.3527 | 0.071* | 0.50 |
H4B2 | 0.3457 | 1.0025 | 0.3265 | 0.071* | 0.50 |
C5B | 0.3982 (6) | 0.8638 (11) | 0.4139 (4) | 0.0588 (14) | 0.50 |
H5B1 | 0.4135 | 0.9414 | 0.4486 | 0.071* | 0.50 |
H5B2 | 0.3718 | 0.7832 | 0.4342 | 0.071* | 0.50 |
C6B | 0.4903 (6) | 0.8187 (12) | 0.3946 (5) | 0.051 (2) | 0.50 |
H6B | 0.5144 | 0.8987 | 0.3715 | 0.061* | 0.50 |
C7B | 0.4707 (15) | 0.688 (3) | 0.3465 (12) | 0.0588 (14) | 0.50 |
H7B1 | 0.4662 | 0.6038 | 0.3745 | 0.071* | 0.50 |
H7B2 | 0.5263 | 0.6746 | 0.3274 | 0.071* | 0.50 |
C8 | 0.5720 (3) | 0.7739 (6) | 0.4658 (3) | 0.0711 (14) | |
C9 | 0.6592 (3) | 0.8420 (5) | 0.4667 (2) | 0.0612 (11) | |
H9 | 0.6611 | 0.9020 | 0.4291 | 0.073* | |
C10 | 0.7440 (3) | 0.8217 (4) | 0.5234 (2) | 0.0528 (9) | |
H10 | 0.8023 | 0.8685 | 0.5234 | 0.063* | |
C11 | 0.7430 (3) | 0.7336 (5) | 0.5794 (2) | 0.0538 (9) | |
H11 | 0.8002 | 0.7205 | 0.6171 | 0.065* | |
C12 | 0.6567 (3) | 0.6648 (6) | 0.5793 (3) | 0.0705 (12) | |
H12 | 0.6551 | 0.6043 | 0.6168 | 0.085* | |
C13 | 0.5718 (3) | 0.6866 (6) | 0.5224 (3) | 0.0806 (16) | |
H13 | 0.5133 | 0.6408 | 0.5227 | 0.097* | |
C14 | 0.1131 (4) | 0.5802 (6) | 0.2979 (2) | 0.0703 (12) | |
H14A | 0.0843 | 0.6731 | 0.3006 | 0.106* | |
H14B | 0.1819 | 0.5817 | 0.3250 | 0.106* | |
H14C | 0.0791 | 0.5085 | 0.3172 | 0.106* | |
C15 | 0.1576 (5) | 0.3580 (6) | 0.2137 (3) | 0.0924 (18) | |
H15A | 0.2282 | 0.3659 | 0.2331 | 0.139* | |
H15B | 0.1419 | 0.3144 | 0.1673 | 0.139* | |
H15C | 0.1318 | 0.2995 | 0.2446 | 0.139* | |
C16 | −0.0301 (4) | 0.4970 (8) | 0.1689 (4) | 0.108 (2) | |
H16A | −0.0503 | 0.4318 | 0.2000 | 0.162* | |
H16B | −0.0414 | 0.4533 | 0.1227 | 0.162* | |
H16C | −0.0677 | 0.5845 | 0.1643 | 0.162* | |
C17 | 0.2460 (7) | 1.0381 (7) | 0.1306 (4) | 0.130 (3) | |
H17A | 0.2847 | 1.0260 | 0.1795 | 0.194* | |
H17B | 0.1848 | 1.0853 | 0.1289 | 0.194* | |
H17C | 0.2822 | 1.0957 | 0.1060 | 0.194* | |
C18 | 0.1411 (6) | 0.9086 (10) | −0.0004 (3) | 0.131 (3) | |
H18A | 0.1655 | 0.9942 | −0.0171 | 0.197* | |
H18B | 0.0747 | 0.9250 | 0.0016 | 0.197* | |
H18C | 0.1412 | 0.8303 | −0.0324 | 0.197* | |
C19 | 0.3384 (6) | 0.8276 (11) | 0.0729 (5) | 0.145 (3) | |
H19A | 0.3328 | 0.7439 | 0.0432 | 0.218* | |
H19B | 0.3875 | 0.8107 | 0.1178 | 0.218* | |
H19C | 0.3576 | 0.9091 | 0.0498 | 0.218* | |
C20 | 0.0439 (3) | 0.8123 (5) | 0.1320 (2) | 0.0554 (10) | |
H20A | 0.0173 | 0.8009 | 0.1716 | 0.083* | |
H20B | −0.0034 | 0.7780 | 0.0892 | 0.083* | |
H20C | 0.0574 | 0.9124 | 0.1265 | 0.083* | |
C21 | 0.1195 (4) | 0.5831 (5) | 0.0613 (2) | 0.0681 (12) | |
H21A | 0.1637 | 0.5941 | 0.0325 | 0.102* | |
H21B | 0.0546 | 0.6156 | 0.0350 | 0.102* | |
H21C | 0.1166 | 0.4833 | 0.0737 | 0.102* | |
Co1 | 0.16868 (3) | 0.69957 (5) | 0.14988 (2) | 0.0409 (2) | |
O1 | 0.22006 (17) | 0.8152 (3) | 0.23848 (13) | 0.0436 (6) | |
O2 | 0.2941 (2) | 0.5894 (4) | 0.17176 (15) | 0.0665 (9) | |
P2 | 0.10199 (9) | 0.53792 (12) | 0.20619 (6) | 0.0583 (3) | |
P3 | 0.22019 (9) | 0.86373 (15) | 0.08824 (6) | 0.0626 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.047 (2) | 0.077 (3) | 0.059 (2) | 0.026 (2) | −0.0057 (18) | −0.028 (2) |
C2 | 0.0403 (19) | 0.056 (2) | 0.046 (2) | 0.0117 (16) | −0.0029 (16) | −0.0164 (17) |
C3 | 0.0372 (18) | 0.047 (2) | 0.0448 (19) | 0.0013 (14) | 0.0054 (15) | −0.0117 (15) |
C4A | 0.0450 (16) | 0.066 (3) | 0.0544 (18) | 0.0138 (15) | −0.0031 (14) | −0.0238 (17) |
C5A | 0.0450 (16) | 0.066 (3) | 0.0544 (18) | 0.0138 (15) | −0.0031 (14) | −0.0238 (17) |
C6A | 0.032 (4) | 0.068 (6) | 0.045 (5) | −0.001 (4) | 0.004 (3) | −0.015 (4) |
C7A | 0.0450 (16) | 0.066 (3) | 0.0544 (18) | 0.0138 (15) | −0.0031 (14) | −0.0238 (17) |
C4B | 0.0450 (16) | 0.066 (3) | 0.0544 (18) | 0.0138 (15) | −0.0031 (14) | −0.0238 (17) |
C5B | 0.0450 (16) | 0.066 (3) | 0.0544 (18) | 0.0138 (15) | −0.0031 (14) | −0.0238 (17) |
C6B | 0.032 (4) | 0.070 (7) | 0.045 (5) | −0.003 (4) | 0.002 (4) | −0.008 (4) |
C7B | 0.0450 (16) | 0.066 (3) | 0.0544 (18) | 0.0138 (15) | −0.0031 (14) | −0.0238 (17) |
C8 | 0.045 (2) | 0.091 (4) | 0.059 (3) | 0.018 (2) | −0.013 (2) | −0.037 (3) |
C9 | 0.068 (3) | 0.060 (2) | 0.044 (2) | 0.017 (2) | −0.0030 (19) | −0.0113 (18) |
C10 | 0.048 (2) | 0.054 (2) | 0.049 (2) | −0.0056 (17) | 0.0014 (17) | −0.0088 (17) |
C11 | 0.041 (2) | 0.060 (2) | 0.051 (2) | −0.0029 (17) | −0.0020 (16) | −0.0057 (18) |
C12 | 0.056 (3) | 0.083 (3) | 0.068 (3) | −0.013 (2) | 0.011 (2) | −0.005 (2) |
C13 | 0.041 (2) | 0.100 (4) | 0.095 (4) | −0.016 (2) | 0.011 (2) | −0.041 (3) |
C14 | 0.081 (3) | 0.071 (3) | 0.060 (3) | −0.002 (2) | 0.023 (2) | 0.014 (2) |
C15 | 0.137 (5) | 0.049 (3) | 0.082 (4) | 0.013 (3) | 0.018 (3) | 0.006 (2) |
C16 | 0.073 (3) | 0.111 (5) | 0.112 (5) | −0.039 (3) | −0.015 (3) | 0.039 (4) |
C17 | 0.200 (9) | 0.068 (4) | 0.147 (7) | −0.038 (5) | 0.094 (7) | 0.002 (4) |
C18 | 0.131 (6) | 0.165 (7) | 0.083 (4) | −0.028 (5) | 0.007 (4) | 0.065 (5) |
C19 | 0.104 (5) | 0.196 (9) | 0.174 (8) | −0.001 (6) | 0.102 (6) | 0.018 (7) |
C20 | 0.039 (2) | 0.071 (3) | 0.051 (2) | 0.0045 (18) | 0.0064 (17) | 0.0070 (19) |
C21 | 0.074 (3) | 0.072 (3) | 0.042 (2) | 0.006 (2) | −0.0099 (19) | −0.017 (2) |
Co1 | 0.0373 (3) | 0.0430 (3) | 0.0352 (3) | 0.00283 (18) | −0.0010 (2) | −0.00375 (18) |
O1 | 0.0340 (12) | 0.0474 (14) | 0.0433 (13) | 0.0069 (10) | 0.0016 (10) | −0.0100 (10) |
O2 | 0.0526 (16) | 0.077 (2) | 0.0533 (16) | 0.0230 (14) | −0.0101 (13) | −0.0320 (15) |
P2 | 0.0603 (6) | 0.0510 (6) | 0.0514 (6) | −0.0060 (5) | −0.0028 (5) | 0.0062 (4) |
P3 | 0.0606 (7) | 0.0753 (8) | 0.0574 (6) | −0.0078 (6) | 0.0259 (5) | 0.0036 (5) |
C1—O2 | 1.271 (5) | C12—C13 | 1.393 (7) |
C1—C2 | 1.394 (5) | C12—H12 | 0.9300 |
C1—H1 | 0.9300 | C13—H13 | 0.9300 |
C2—C3 | 1.403 (5) | C14—P2 | 1.800 (5) |
C2—C7B | 1.521 (10) | C14—H14A | 0.9600 |
C2—C7A | 1.526 (10) | C14—H14B | 0.9600 |
C3—O1 | 1.265 (4) | C14—H14C | 0.9600 |
C3—C4A | 1.523 (10) | C15—P2 | 1.831 (5) |
C3—C4B | 1.509 (10) | C15—H15A | 0.9600 |
C4A—C5A | 1.569 (12) | C15—H15B | 0.9600 |
C4A—H4A1 | 0.9700 | C15—H15C | 0.9600 |
C4A—H4A2 | 0.9700 | C16—P2 | 1.832 (5) |
C5A—C6A | 1.534 (11) | C16—H16A | 0.9600 |
C5A—H5A1 | 0.9700 | C16—H16B | 0.9600 |
C5A—H5A2 | 0.9700 | C16—H16C | 0.9600 |
C6A—C7A | 1.510 (16) | C17—P3 | 1.806 (7) |
C6A—C8 | 1.533 (9) | C17—H17A | 0.9600 |
C6A—H6A | 0.9800 | C17—H17B | 0.9600 |
C7A—H7A1 | 0.9700 | C17—H17C | 0.9600 |
C7A—H7A2 | 0.9700 | C18—P3 | 1.817 (6) |
C4B—C5B | 1.565 (12) | C18—H18A | 0.9600 |
C4B—H4B1 | 0.9700 | C18—H18B | 0.9600 |
C4B—H4B2 | 0.9700 | C18—H18C | 0.9600 |
C5B—C6B | 1.514 (10) | C19—P3 | 1.810 (6) |
C5B—H5B1 | 0.9700 | C19—H19A | 0.9600 |
C5B—H5B2 | 0.9700 | C19—H19B | 0.9600 |
C6B—C7B | 1.508 (16) | C19—H19C | 0.9600 |
C6B—C8 | 1.584 (10) | C20—Co1 | 1.990 (4) |
C6B—H6B | 0.9800 | C20—H20A | 0.9600 |
C7B—H7B1 | 0.9700 | C20—H20B | 0.9600 |
C7B—H7B2 | 0.9700 | C20—H20C | 0.9600 |
C8—C13 | 1.372 (8) | C21—Co1 | 1.989 (4) |
C8—C9 | 1.377 (7) | C21—H21A | 0.9600 |
C9—C10 | 1.388 (6) | C21—H21B | 0.9600 |
C9—H9 | 0.9300 | C21—H21C | 0.9600 |
C10—C11 | 1.370 (6) | Co1—O2 | 1.980 (3) |
C10—H10 | 0.9300 | Co1—O1 | 1.987 (2) |
C11—C12 | 1.374 (6) | Co1—P3 | 2.1938 (13) |
C11—H11 | 0.9300 | Co1—P2 | 2.2254 (13) |
O2—C1—C2 | 129.3 (4) | C8—C13—C12 | 121.8 (5) |
O2—C1—H1 | 115.4 | C8—C13—H13 | 119.1 |
C2—C1—H1 | 115.4 | C12—C13—H13 | 119.1 |
C1—C2—C3 | 122.2 (3) | P2—C14—H14A | 109.5 |
C1—C2—C7B | 116.5 (5) | P2—C14—H14B | 109.5 |
C3—C2—C7B | 121.3 (5) | H14A—C14—H14B | 109.5 |
C1—C2—C7A | 117.0 (5) | P2—C14—H14C | 109.5 |
C3—C2—C7A | 120.8 (5) | H14A—C14—H14C | 109.5 |
C7B—C2—C7A | 3 (3) | H14B—C14—H14C | 109.5 |
O1—C3—C2 | 125.7 (3) | P2—C15—H15A | 109.5 |
O1—C3—C4A | 114.7 (5) | P2—C15—H15B | 109.5 |
C2—C3—C4A | 119.4 (5) | H15A—C15—H15B | 109.5 |
O1—C3—C4B | 113.6 (5) | P2—C15—H15C | 109.5 |
C2—C3—C4B | 120.6 (5) | H15A—C15—H15C | 109.5 |
C4A—C3—C4B | 9.6 (15) | H15B—C15—H15C | 109.5 |
C3—C4A—C5A | 114.4 (8) | P2—C16—H16A | 109.5 |
C3—C4A—H4A1 | 108.6 | P2—C16—H16B | 109.5 |
C5A—C4A—H4A1 | 108.6 | H16A—C16—H16B | 109.5 |
C3—C4A—H4A2 | 108.7 | P2—C16—H16C | 109.5 |
C5A—C4A—H4A2 | 108.7 | H16A—C16—H16C | 109.5 |
H4A1—C4A—H4A2 | 107.6 | H16B—C16—H16C | 109.5 |
C6A—C5A—C4A | 105.6 (8) | P3—C17—H17A | 109.5 |
C6A—C5A—H5A1 | 110.6 | P3—C17—H17B | 109.5 |
C4A—C5A—H5A1 | 110.6 | H17A—C17—H17B | 109.5 |
C6A—C5A—H5A2 | 110.6 | P3—C17—H17C | 109.5 |
C4A—C5A—H5A2 | 110.6 | H17A—C17—H17C | 109.5 |
H5A1—C5A—H5A2 | 108.8 | H17B—C17—H17C | 109.5 |
C5A—C6A—C7A | 108.7 (13) | P3—C18—H18A | 109.5 |
C5A—C6A—C8 | 108.0 (7) | P3—C18—H18B | 109.5 |
C7A—C6A—C8 | 109.3 (8) | H18A—C18—H18B | 109.5 |
C5A—C6A—H6A | 110.2 | P3—C18—H18C | 109.5 |
C7A—C6A—H6A | 110.2 | H18A—C18—H18C | 109.5 |
C8—C6A—H6A | 110.2 | H18B—C18—H18C | 109.5 |
C6A—C7A—C2 | 113.8 (11) | P3—C19—H19A | 109.5 |
C6A—C7A—H7A1 | 108.8 | P3—C19—H19B | 109.5 |
C2—C7A—H7A1 | 108.8 | H19A—C19—H19B | 109.5 |
C6A—C7A—H7A2 | 108.8 | P3—C19—H19C | 109.5 |
C2—C7A—H7A2 | 108.8 | H19A—C19—H19C | 109.5 |
H7A1—C7A—H7A2 | 107.7 | H19B—C19—H19C | 109.5 |
C3—C4B—C5B | 111.9 (8) | Co1—C20—H20A | 109.5 |
C3—C4B—H4B1 | 109.2 | Co1—C20—H20B | 109.5 |
C5B—C4B—H4B1 | 109.2 | H20A—C20—H20B | 109.5 |
C3—C4B—H4B2 | 109.2 | Co1—C20—H20C | 109.5 |
C5B—C4B—H4B2 | 109.2 | H20A—C20—H20C | 109.5 |
H4B1—C4B—H4B2 | 107.9 | H20B—C20—H20C | 109.5 |
C6B—C5B—C4B | 106.8 (9) | Co1—C21—H21A | 109.5 |
C6B—C5B—H5B1 | 110.4 | Co1—C21—H21B | 109.5 |
C4B—C5B—H5B1 | 110.4 | H21A—C21—H21B | 109.5 |
C6B—C5B—H5B2 | 110.4 | Co1—C21—H21C | 109.5 |
C4B—C5B—H5B2 | 110.4 | H21A—C21—H21C | 109.5 |
H5B1—C5B—H5B2 | 108.6 | H21B—C21—H21C | 109.5 |
C5B—C6B—C7B | 111.3 (13) | O2—Co1—O1 | 90.80 (10) |
C5B—C6B—C8 | 108.1 (7) | O2—Co1—C21 | 88.33 (16) |
C7B—C6B—C8 | 107.1 (10) | O1—Co1—C21 | 179.06 (16) |
C5B—C6B—H6B | 110.1 | O2—Co1—C20 | 177.72 (14) |
C7B—C6B—H6B | 110.1 | O1—Co1—C20 | 87.09 (15) |
C8—C6B—H6B | 110.1 | C21—Co1—C20 | 93.79 (19) |
C6B—C7B—C2 | 113.3 (11) | O2—Co1—P3 | 93.37 (12) |
C6B—C7B—H7B1 | 108.9 | O1—Co1—P3 | 90.61 (9) |
C2—C7B—H7B1 | 108.9 | C21—Co1—P3 | 89.12 (16) |
C6B—C7B—H7B2 | 108.9 | C20—Co1—P3 | 87.51 (13) |
C2—C7B—H7B2 | 108.9 | O2—Co1—P2 | 91.46 (12) |
H7B1—C7B—H7B2 | 107.7 | O1—Co1—P2 | 91.75 (9) |
C13—C8—C9 | 118.2 (4) | C21—Co1—P2 | 88.60 (16) |
C13—C8—C6A | 105.8 (6) | C20—Co1—P2 | 87.76 (13) |
C9—C8—C6A | 136.0 (6) | P3—Co1—P2 | 174.60 (5) |
C13—C8—C6B | 133.8 (6) | C3—O1—Co1 | 127.5 (2) |
C9—C8—C6B | 108.0 (6) | C1—O2—Co1 | 124.5 (2) |
C6A—C8—C6B | 28.1 (4) | C14—P2—C15 | 102.0 (3) |
C8—C9—C10 | 120.4 (5) | C14—P2—C16 | 103.1 (3) |
C8—C9—H9 | 119.8 | C15—P2—C16 | 101.9 (3) |
C10—C9—H9 | 119.8 | C14—P2—Co1 | 114.89 (17) |
C11—C10—C9 | 120.8 (4) | C15—P2—Co1 | 114.9 (2) |
C11—C10—H10 | 119.6 | C16—P2—Co1 | 118.0 (2) |
C9—C10—H10 | 119.6 | C17—P3—C19 | 99.8 (5) |
C10—C11—C12 | 119.5 (4) | C17—P3—C18 | 102.7 (4) |
C10—C11—H11 | 120.3 | C19—P3—C18 | 102.9 (4) |
C12—C11—H11 | 120.3 | C17—P3—Co1 | 115.1 (2) |
C11—C12—C13 | 119.3 (5) | C19—P3—Co1 | 115.6 (3) |
C11—C12—H12 | 120.4 | C18—P3—Co1 | 118.3 (2) |
C13—C12—H12 | 120.4 |
Experimental details
Crystal data | |
Chemical formula | [Co(CH3)2(C13H13O2)(C3H9P)2] |
Mr | 442.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 423 |
a, b, c (Å) | 14.109 (3), 9.2740 (19), 19.577 (4) |
β (°) | 106.94 (3) |
V (Å3) | 2450.4 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.84 |
Crystal size (mm) | 0.32 × 0.20 × 0.12 |
Data collection | |
Diffractometer | CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.774, 0.906 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15313, 4287, 3853 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.171, 1.05 |
No. of reflections | 4287 |
No. of parameters | 249 |
No. of restraints | 11 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.68, −0.85 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Bruker, 2000).
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Reaction of substituted enolated malonic dialdehydes (enol-form: b-keton-aldehyde) with [CoMe3(PMe3)3] was recently reported (Li et al., 2005). 2-Hydroxy-5-phenyl-cyclohex-1-enecarbaldehyde reacts with [CoMe3(PMe3)3] (Scheme) by elimination of methane and trimethylphosphine utilizing both the phenolato and the keto-oxygen functions to afford the hexacoordinate title cobalt(III) complex as red solids that are soluble in pentane or diethyl ether. Single crystals suitable for X-ray diffraction analysis of title compound were obtained.
A view of the molecular structure is given in Figure 1. Cobalt atom displays an octahedral coordination with two equatorial cis-methyl groups (C20 and C21) and two axial trimethylphosphines as well as a bidentate ligand. The angle P1–Co–P2 of 174.59 (5) implies a slight distortion from an ideal octahedron. The substituted salicylaldehyde ligands have Co—O bond lengths of Co1—O1 1.987 (2), Co1—O2 1.980 (3). The chelate ring is planar with the largest deviation from the plane being 0.030 (3)Å at O2.