trans-Bis(pyridine)­bis[3,3,3-trifluoro-1-(4-methoxy­benzo­yl)prop-1-en-2-olato]cobalt(II)

The title compound, [Co(C₁₁H₉F₃O₃)₂(C₅H₅N)₂], has an octa­hedral cobalt(II) centre. The crystal structure is stabilized by weak C—H...π inter­actions between a benzene H atom and a neighboring pyridine ring.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](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

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S1. Comment

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 Co^II 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).

Related literature

For the applications of the title compound, see: Soldatov et al. (2003). For the synthesis, see: Sloopa et al., 2002)

S2. Experimental

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.

S3. Refinement

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 U_iso(H) = 1.2U_eq(C).

Computing details

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).

Figures

	Fig. 1. The molecular structure of the title compound. Showing displacement ellipsoids drawn at the 30% probability level. [Symmetry code: (i) -x + 1, -y + 1, -z + 1.]
	Fig. 2. C—H···π interaction (dotted lines) in the title compound. Cg denotes ring centroid. [Symmetry code: (i) x + 1, y, z; (ii) -x + 1, -y + 1, -z + 1.]

trans-Dipyridinebis[3,3,3-trifluoro-1-(4-methoxybenzoyl)prop-1-en-2- olato]cobalt(II)

Crystal data

[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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0597P)^2] where P = (Fo^2 + 2Fc^2)/3
3027 reflections	(Δ/σ)max < 0.001
215 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

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 (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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—O2^i	2.0408 (15)
C8—C9	1.412 (3)	Co—O3^i	2.0603 (17)
C9—C10	1.374 (3)	Co—O3	2.0603 (17)
C9—H9	0.9300	Co—N^i	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—O2^i	179.999 (1)
C4—C5—C8	124.3 (2)	O2—Co—O3^i	91.06 (6)
C5—C6—C7	123.2 (2)	O2^i—Co—O3^i	88.94 (6)
C5—C6—H6	118.4	O2—Co—O3	88.94 (6)
C7—C6—H6	118.4	O2^i—Co—O3	91.06 (6)
C2—C7—C6	118.8 (2)	O3^i—Co—O3	180.000 (1)
C2—C7—H7	120.6	O2—Co—N^i	90.34 (8)
C6—C7—H7	120.6	O2^i—Co—N^i	89.66 (8)
O2—C8—C9	123.1 (2)	O3^i—Co—N^i	88.90 (8)
O2—C8—C5	116.5 (2)	O3—Co—N^i	91.10 (8)
C9—C8—C5	120.4 (2)	O2—Co—N	89.66 (8)
C10—C9—C8	124.9 (2)	O2^i—Co—N	90.34 (8)
C10—C9—H9	117.6	O3^i—Co—N	91.10 (8)
C8—C9—H9	117.6	O3—Co—N	88.90 (8)
O3—C10—C9	130.4 (2)	N^i—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)	O2^i—Co—N—C16	−147.6 (2)
O1—C2—C7—C6	179.0 (2)	O3^i—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)	O2^i—Co—N—C12	30.1 (2)
C4—C5—C8—O2	−172.1 (2)	O3^i—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)	O3^i—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)	N^i—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)	O2^i—Co—O3—C10	−168.98 (19)
C12—C13—C14—C15	0.5 (5)	N^i—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.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg^ii	0.93	3.22	3.884 (3)	131

Symmetry code: (ii) −x, −y+1, −z+1.