Bis[4-(2-benzoyl-1-oxidoethen­yl)-3-hy­droxy­phenyl benzoato]diethano­l­cobalt(II)

Bai, X.-L.; Yue, T.-L.; Yuan, Y.-H.; Zhang, H.-W.

doi:10.1107/S1600536810029776

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Pages m1038-m1039

https://doi.org/10.1107/S1600536810029776

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Bis[4-(2-benzoyl-1-oxidoethenyl)-3-hydroxyphenyl benzoato]diethanolcobalt(II)

Xue-Lian Bai,^a Tian-Li Yue,^a ^* Ya-Hong Yuan ^a and Hua-Wei Zhang ^b

^aCollege of Food Science and Engineering, Northwest A&F University, Yangling 712100, People's Republic of China, and ^bSchool of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: ytl6503@163.com

(Received 26 July 2010; accepted 27 July 2010; online 31 July 2010)

In the title complex, [Co(C₂₂H₁₅O₅)₂(C₂H₅OH)₂], the Co^II atom (site symmetry $[\overline{1}]$ ) is coordinated by two O,O′-bidentate 4-(2-benzoyl-1-oxidoethenyl)-3-hydroxyphenyl benzoate anions and two ethanol O atoms, resulting in a slightly distorted CoO₆ octahedral coordination. An intramolecular O—H⋯O hydrogen bond in the ligand generates an S(6) ring. The dihedral angle between the aromatic rings joined to the acetylacetonate unit is 6.4 (2)°. The ethanol molecule is disordered over two orientations in a 0.65 (3):0.35 (3) ratio. In the crystal, molecules are linked by O—H⋯O bonds.

Related literature

For background to related cobalt complexes, see: Shi et al. (2008 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Co(C₂₂H₁₅O₅)₂(C₂H₆O)₂]
M_r = 869.75
Triclinic, $[P \overline 1]$
a = 7.2068 (9) Å
b = 9.4298 (12) Å
c = 16.5511 (19) Å
α = 106.358 (1)°
β = 95.431 (2)°
γ = 90.920 (1)°
V = 1073.3 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 298 K
0.38 × 0.15 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.844, T_max = 0.955
5612 measured reflections
3716 independent reflections
1953 reflections with I > 2σ(I)
R_int = 0.039
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.161
S = 0.95
3716 reflections
296 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O1	2.015 (2)
Co1—O2	2.033 (3)
Co1—O6	2.184 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	1.76	2.489 (4)	147
O6—H6⋯O3ⁱ	0.85	2.02	2.855 (4)	168
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810029776/hb5579sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810029776/hb5579Isup2.hkl

checkCIF report

Comment top

There has been much research interest in cobalt complexes due to their molecular architectures and biological activities (Shi et al., 2008). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The Co^II atom is six-coordinated by four O atoms from the 3-hydroxy-4-(1-hydroxy-3-oxo-3-phenylprop-1-enyl)phenyl benzoate and two O atoms from the ethanol molecules, forming a slightly distorted octahedral coordination. There is an intermolecuar and an intramolecular O—H···O hydrogen bonds in the title complex.

Related literature top

For background to related cobalt complexes, see: Shi et al. (2008). For reference structural data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by stirring a mixture of 3-hydroxy-4-(1-hydroxy-3-oxo-3-phenylprop-1-enyl)phenyl benzoate (720 mg, 2 mmol) and CoCl₂.6H₂O (1 mmol, 238 mg) in ethanol (10 ml) for 3 h. After keeping the filtrate in air for 8 d, red block-shaped crystals of (I) were formed.

Structure description top

For background to related cobalt complexes, see: Shi et al. (2008). For reference structural data, see: Allen et al. (1987).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids. Atoms with suffix A are generated by (1–x, 1–y, 1–z).

Bis[4-(2-benzoyl-1-oxidoethenyl)-3-hydroxyphenyl benzoato]diethanolcobalt(II) top

Crystal data top

[Co(C₂₂H₁₅O₅)₂(C₂H₆O)₂]	Z = 1
M_r = 869.75	F(000) = 453
Triclinic, P1	D_x = 1.346 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2068 (9) Å	Cell parameters from 25 reflections
b = 9.4298 (12) Å	θ = 9–12°
c = 16.5511 (19) Å	µ = 0.46 mm⁻¹
α = 106.358 (1)°	T = 298 K
β = 95.431 (2)°	Block, red
γ = 90.920 (1)°	0.38 × 0.15 × 0.10 mm
V = 1073.3 (2) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	1953 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 25.0°, θ_min = 2.3°
ω/2θ scan	h = −8→7
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
T_min = 0.844, T_max = 0.955	l = −19→19
5612 measured reflections	3 standard reflections every 200 reflections
3716 independent reflections	intensity decay: 1%

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0689P)²] where P = (F_o² + 2F_c²)/3
3716 reflections	(Δ/σ)_max = 0.001
296 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Co(C₂₂H₁₅O₅)₂(C₂H₆O)₂]	γ = 90.920 (1)°
M_r = 869.75	V = 1073.3 (2) Å³
Triclinic, P1	Z = 1
a = 7.2068 (9) Å	Mo Kα radiation
b = 9.4298 (12) Å	µ = 0.46 mm⁻¹
c = 16.5511 (19) Å	T = 298 K
α = 106.358 (1)°	0.38 × 0.15 × 0.10 mm
β = 95.431 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1953 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.039
T_min = 0.844, T_max = 0.955	3 standard reflections every 200 reflections
5612 measured reflections	intensity decay: 1%
3716 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 0.95	Δρ_max = 0.33 e Å⁻³
3716 reflections	Δρ_min = −0.39 e Å⁻³
296 parameters

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	U_iso*/U_eq	Occ. (<1)
Co1	0.5000	0.5000	0.5000	0.0624 (4)
O1	0.6698 (4)	0.3797 (3)	0.55579 (17)	0.0628 (9)
O2	0.3392 (4)	0.5269 (4)	0.59728 (17)	0.0651 (9)
O3	0.0547 (4)	0.6632 (4)	0.63944 (17)	0.0761 (11)
H3	0.1307	0.6221	0.6077	0.114*
O4	−0.0989 (4)	0.7618 (4)	0.92129 (19)	0.0698 (9)
O5	−0.2457 (5)	0.5537 (4)	0.9277 (2)	0.0889 (12)
O6	0.3197 (5)	0.3103 (4)	0.4264 (2)	0.0835 (11)
H6	0.2093	0.3309	0.4121	0.100*
C1	0.6744 (6)	0.3714 (5)	0.6316 (3)	0.0496 (11)
C2	0.5426 (6)	0.4316 (5)	0.6878 (2)	0.0553 (12)
H2	0.5644	0.4225	0.7424	0.066*
C3	0.3823 (6)	0.5036 (5)	0.6703 (2)	0.0487 (11)
C4	0.2513 (5)	0.5608 (5)	0.7353 (2)	0.0481 (11)
C5	0.0949 (6)	0.6410 (5)	0.7169 (2)	0.0507 (11)
C6	−0.0226 (6)	0.7014 (5)	0.7786 (3)	0.0587 (12)
H6A	−0.1229	0.7551	0.7661	0.070*
C7	0.0089 (6)	0.6822 (5)	0.8575 (3)	0.0582 (12)
C8	0.1538 (6)	0.5989 (5)	0.8769 (3)	0.0658 (14)
H8	0.1708	0.5818	0.9297	0.079*
C9	0.2720 (6)	0.5420 (5)	0.8164 (3)	0.0597 (13)
H9	0.3710	0.4882	0.8302	0.072*
C10	0.8321 (6)	0.2857 (5)	0.6592 (2)	0.0510 (12)
C11	0.9469 (7)	0.2133 (6)	0.6006 (3)	0.0824 (18)
H11	0.9284	0.2200	0.5454	0.099*
C12	1.0905 (8)	0.1300 (7)	0.6226 (3)	0.100 (2)
H12	1.1665	0.0814	0.5821	0.120*
C13	1.1205 (8)	0.1191 (6)	0.7038 (3)	0.0886 (18)
H13	1.2125	0.0597	0.7181	0.106*
C14	1.0137 (8)	0.1964 (6)	0.7625 (3)	0.0873 (19)
H14	1.0363	0.1935	0.8182	0.105*
C15	0.8721 (7)	0.2792 (6)	0.7409 (3)	0.0714 (15)
H15	0.8016	0.3322	0.7827	0.086*
C16	−0.2220 (7)	0.6860 (6)	0.9529 (3)	0.0588 (12)
C17	−0.3227 (6)	0.7882 (5)	1.0192 (2)	0.0515 (12)
C18	−0.2748 (7)	0.9379 (6)	1.0524 (3)	0.0638 (13)
H18	−0.1730	0.9787	1.0348	0.077*
C19	−0.3782 (7)	1.0260 (6)	1.1114 (3)	0.0751 (15)
H19	−0.3452	1.1261	1.1341	0.090*
C20	−0.5292 (8)	0.9668 (7)	1.1368 (3)	0.0784 (17)
H20	−0.5986	1.0270	1.1764	0.094*
C21	−0.5791 (8)	0.8193 (7)	1.1042 (3)	0.0843 (17)
H21	−0.6831	0.7798	1.1208	0.101*
C22	−0.4739 (7)	0.7297 (6)	1.0465 (3)	0.0697 (14)
H22	−0.5051	0.6290	1.0258	0.084*
C23	0.3217 (17)	0.1644 (13)	0.4320 (14)	0.087 (5)	0.65 (3)
H23A	0.2041	0.1119	0.4068	0.104*	0.65 (3)
H23B	0.3398	0.1644	0.4909	0.104*	0.65 (3)
C24	0.479 (6)	0.090 (5)	0.3856 (19)	0.116 (8)	0.65 (3)
H24A	0.4836	0.1185	0.3344	0.174*	0.65 (3)
H24B	0.4601	−0.0151	0.3719	0.174*	0.65 (3)
H24C	0.5951	0.1202	0.4207	0.174*	0.65 (3)
C23'	0.348 (3)	0.165 (2)	0.375 (3)	0.087 (8)	0.35 (3)
H23C	0.4117	0.1730	0.3273	0.104*	0.35 (3)
H23D	0.2272	0.1159	0.3526	0.104*	0.35 (3)
C24'	0.458 (11)	0.067 (9)	0.418 (3)	0.116 (14)	0.35 (3)
H24D	0.5487	0.1267	0.4610	0.174*	0.35 (3)
H24E	0.5215	−0.0033	0.3770	0.174*	0.35 (3)
H24F	0.3755	0.0156	0.4433	0.174*	0.35 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0504 (6)	0.0955 (8)	0.0497 (5)	0.0298 (5)	0.0152 (4)	0.0298 (5)
O1	0.053 (2)	0.094 (2)	0.0492 (17)	0.0336 (18)	0.0160 (15)	0.0283 (17)
O2	0.053 (2)	0.102 (3)	0.0502 (17)	0.0321 (18)	0.0154 (15)	0.0323 (17)
O3	0.056 (2)	0.123 (3)	0.0579 (19)	0.044 (2)	0.0174 (16)	0.0331 (19)
O4	0.064 (2)	0.072 (2)	0.077 (2)	0.0116 (18)	0.0381 (18)	0.0150 (18)
O5	0.093 (3)	0.066 (3)	0.104 (3)	0.003 (2)	0.051 (2)	0.005 (2)
O6	0.058 (2)	0.090 (3)	0.100 (3)	0.027 (2)	−0.002 (2)	0.024 (2)
C1	0.040 (3)	0.061 (3)	0.049 (3)	0.014 (2)	0.005 (2)	0.017 (2)
C2	0.045 (3)	0.080 (3)	0.048 (2)	0.022 (3)	0.013 (2)	0.027 (2)
C3	0.039 (3)	0.061 (3)	0.048 (2)	0.011 (2)	0.008 (2)	0.017 (2)
C4	0.034 (2)	0.062 (3)	0.051 (2)	0.012 (2)	0.010 (2)	0.016 (2)
C5	0.041 (3)	0.067 (3)	0.045 (2)	0.009 (2)	0.010 (2)	0.015 (2)
C6	0.042 (3)	0.074 (3)	0.062 (3)	0.018 (2)	0.018 (2)	0.018 (2)
C7	0.048 (3)	0.065 (3)	0.062 (3)	0.010 (3)	0.023 (2)	0.012 (2)
C8	0.058 (3)	0.088 (4)	0.058 (3)	0.014 (3)	0.020 (3)	0.027 (3)
C9	0.049 (3)	0.083 (4)	0.055 (3)	0.024 (3)	0.016 (2)	0.029 (2)
C10	0.043 (3)	0.067 (3)	0.049 (3)	0.014 (2)	0.010 (2)	0.023 (2)
C11	0.073 (4)	0.123 (5)	0.057 (3)	0.053 (4)	0.019 (3)	0.028 (3)
C12	0.082 (4)	0.142 (6)	0.083 (4)	0.074 (4)	0.025 (3)	0.034 (4)
C13	0.078 (4)	0.115 (5)	0.082 (4)	0.045 (4)	0.004 (3)	0.042 (3)
C14	0.085 (4)	0.129 (5)	0.066 (3)	0.052 (4)	0.014 (3)	0.052 (3)
C15	0.065 (3)	0.104 (4)	0.058 (3)	0.035 (3)	0.017 (3)	0.038 (3)
C16	0.051 (3)	0.071 (4)	0.058 (3)	0.007 (3)	0.018 (2)	0.018 (3)
C17	0.048 (3)	0.064 (3)	0.044 (2)	0.010 (3)	0.011 (2)	0.017 (2)
C18	0.055 (3)	0.076 (4)	0.059 (3)	0.004 (3)	0.018 (3)	0.013 (3)
C19	0.074 (4)	0.075 (4)	0.068 (3)	0.006 (3)	0.013 (3)	0.006 (3)
C20	0.084 (4)	0.096 (5)	0.057 (3)	0.026 (4)	0.033 (3)	0.016 (3)
C21	0.079 (4)	0.100 (5)	0.086 (4)	0.009 (4)	0.047 (3)	0.032 (4)
C22	0.069 (3)	0.071 (4)	0.074 (3)	0.006 (3)	0.032 (3)	0.020 (3)
C23	0.072 (7)	0.096 (9)	0.094 (10)	0.027 (6)	0.011 (7)	0.030 (7)
C24	0.110 (14)	0.114 (16)	0.12 (2)	0.037 (12)	0.017 (16)	0.017 (14)
C23'	0.072 (13)	0.097 (16)	0.09 (2)	0.027 (11)	0.011 (12)	0.030 (13)
C24'	0.11 (3)	0.11 (3)	0.12 (4)	0.04 (2)	0.02 (3)	0.02 (3)

Geometric parameters (Å, º) top

Co1—O1ⁱ	2.015 (2)	C11—H11	0.9300
Co1—O1	2.015 (2)	C12—C13	1.373 (6)
Co1—O2ⁱ	2.033 (3)	C12—H12	0.9300
Co1—O2	2.033 (3)	C13—C14	1.352 (6)
Co1—O6ⁱ	2.184 (4)	C13—H13	0.9300
Co1—O6	2.184 (4)	C14—C15	1.376 (6)
O1—C1	1.276 (4)	C14—H14	0.9300
O2—C3	1.299 (4)	C15—H15	0.9300
O3—C5	1.361 (4)	C16—C17	1.495 (6)
O3—H3	0.8200	C17—C22	1.382 (6)
O4—C16	1.360 (5)	C17—C18	1.388 (6)
O4—C7	1.417 (5)	C18—C19	1.379 (6)
O5—C16	1.202 (5)	C18—H18	0.9300
O6—C23	1.405 (13)	C19—C20	1.368 (7)
O6—C23'	1.43 (2)	C19—H19	0.9300
O6—H6	0.8500	C20—C21	1.371 (7)
C1—C2	1.406 (5)	C20—H20	0.9300
C1—C10	1.514 (5)	C21—C22	1.379 (6)
C2—C3	1.397 (5)	C21—H21	0.9300
C2—H2	0.9300	C22—H22	0.9300
C3—C4	1.490 (5)	C23—C24	1.50 (5)
C4—C9	1.397 (5)	C23—H23A	0.9700
C4—C5	1.425 (5)	C23—H23B	0.9700
C5—C6	1.392 (5)	C24—H24A	0.9600
C6—C7	1.366 (6)	C24—H24B	0.9600
C6—H6A	0.9300	C24—H24C	0.9600
C7—C8	1.384 (6)	C23'—C24'	1.51 (8)
C8—C9	1.375 (5)	C23'—H23C	0.9700
C8—H8	0.9300	C23'—H23D	0.9700
C9—H9	0.9300	C24'—H24D	0.9600
C10—C11	1.374 (5)	C24'—H24E	0.9600
C10—C15	1.375 (5)	C24'—H24F	0.9600
C11—C12	1.391 (6)

O1ⁱ—Co1—O1	180.00 (13)	C13—C12—C11	120.4 (5)
O1ⁱ—Co1—O2ⁱ	88.35 (11)	C13—C12—H12	119.8
O1—Co1—O2ⁱ	91.65 (11)	C11—C12—H12	119.8
O1ⁱ—Co1—O2	91.65 (11)	C14—C13—C12	118.6 (4)
O1—Co1—O2	88.35 (11)	C14—C13—H13	120.7
O2ⁱ—Co1—O2	180.000 (1)	C12—C13—H13	120.7
O1ⁱ—Co1—O6ⁱ	94.47 (13)	C13—C14—C15	120.9 (4)
O1—Co1—O6ⁱ	85.53 (13)	C13—C14—H14	119.5
O2ⁱ—Co1—O6ⁱ	89.66 (13)	C15—C14—H14	119.5
O2—Co1—O6ⁱ	90.34 (13)	C10—C15—C14	121.7 (4)
O1ⁱ—Co1—O6	85.53 (13)	C10—C15—H15	119.2
O1—Co1—O6	94.47 (13)	C14—C15—H15	119.2
O2ⁱ—Co1—O6	90.34 (13)	O5—C16—O4	122.5 (4)
O2—Co1—O6	89.66 (13)	O5—C16—C17	126.1 (5)
O6ⁱ—Co1—O6	180.000 (1)	O4—C16—C17	111.4 (5)
C1—O1—Co1	127.4 (2)	C22—C17—C18	119.1 (4)
C3—O2—Co1	127.9 (3)	C22—C17—C16	117.6 (5)
C5—O3—H3	109.5	C18—C17—C16	123.3 (4)
C16—O4—C7	119.1 (4)	C19—C18—C17	119.9 (5)
C23—O6—C23'	40.5 (9)	C19—C18—H18	120.0
C23—O6—Co1	128.0 (6)	C17—C18—H18	120.0
C23'—O6—Co1	135.4 (9)	C20—C19—C18	120.2 (5)
C23—O6—H6	110.0	C20—C19—H19	119.9
C23'—O6—H6	106.9	C18—C19—H19	119.9
Co1—O6—H6	115.0	C19—C20—C21	120.5 (5)
O1—C1—C2	124.7 (4)	C19—C20—H20	119.7
O1—C1—C10	115.6 (3)	C21—C20—H20	119.7
C2—C1—C10	119.7 (3)	C20—C21—C22	119.6 (5)
C3—C2—C1	126.8 (4)	C20—C21—H21	120.2
C3—C2—H2	116.6	C22—C21—H21	120.2
C1—C2—H2	116.6	C21—C22—C17	120.6 (5)
O2—C3—C2	122.5 (4)	C21—C22—H22	119.7
O2—C3—C4	115.8 (3)	C17—C22—H22	119.7
C2—C3—C4	121.7 (3)	O6—C23—C24	108 (2)
C9—C4—C5	115.9 (4)	O6—C23—H23A	110.2
C9—C4—C3	123.8 (4)	C24—C23—H23A	110.2
C5—C4—C3	120.3 (3)	O6—C23—H23B	110.2
O3—C5—C6	117.3 (4)	C24—C23—H23B	110.2
O3—C5—C4	122.1 (4)	H23A—C23—H23B	108.5
C6—C5—C4	120.6 (4)	C23—C24—H24A	109.5
C7—C6—C5	120.3 (4)	C23—C24—H24B	109.5
C7—C6—H6A	119.8	H24A—C24—H24B	109.5
C5—C6—H6A	119.8	C23—C24—H24C	109.5
C6—C7—C8	121.0 (4)	H24A—C24—H24C	109.5
C6—C7—O4	118.1 (4)	H24B—C24—H24C	109.5
C8—C7—O4	120.6 (4)	O6—C23'—C24'	116 (4)
C9—C8—C7	118.5 (4)	O6—C23'—H23C	108.2
C9—C8—H8	120.7	C24'—C23'—H23C	108.2
C7—C8—H8	120.7	O6—C23'—H23D	108.2
C8—C9—C4	123.5 (4)	C24'—C23'—H23D	108.2
C8—C9—H9	118.2	H23C—C23'—H23D	107.4
C4—C9—H9	118.2	C23'—C24'—H24D	109.5
C11—C10—C15	117.2 (4)	C23'—C24'—H24E	109.5
C11—C10—C1	119.0 (4)	H24D—C24'—H24E	109.5
C15—C10—C1	123.8 (4)	C23'—C24'—H24F	109.5
C10—C11—C12	121.0 (4)	H24D—C24'—H24F	109.5
C10—C11—H11	119.5	H24E—C24'—H24F	109.5
C12—C11—H11	119.5

O1ⁱ—Co1—O1—C1	−81 (100)	C5—C6—C7—O4	171.8 (4)
O2ⁱ—Co1—O1—C1	165.4 (4)	C16—O4—C7—C6	113.6 (5)
O2—Co1—O1—C1	−14.6 (4)	C16—O4—C7—C8	−72.5 (6)
O6ⁱ—Co1—O1—C1	75.9 (4)	C6—C7—C8—C9	3.4 (8)
O6—Co1—O1—C1	−104.1 (4)	O4—C7—C8—C9	−170.3 (4)
O1ⁱ—Co1—O2—C3	−164.3 (4)	C7—C8—C9—C4	−1.6 (8)
O1—Co1—O2—C3	15.7 (4)	C5—C4—C9—C8	−1.5 (7)
O2ⁱ—Co1—O2—C3	108 (100)	C3—C4—C9—C8	178.0 (4)
O6ⁱ—Co1—O2—C3	−69.8 (4)	O1—C1—C10—C11	−5.6 (7)
O6—Co1—O2—C3	110.2 (4)	C2—C1—C10—C11	172.5 (5)
O1ⁱ—Co1—O6—C23	−172.1 (11)	O1—C1—C10—C15	172.3 (5)
O1—Co1—O6—C23	7.9 (11)	C2—C1—C10—C15	−9.5 (7)
O2ⁱ—Co1—O6—C23	99.5 (11)	C15—C10—C11—C12	3.6 (8)
O2—Co1—O6—C23	−80.5 (11)	C1—C10—C11—C12	−178.3 (5)
O6ⁱ—Co1—O6—C23	−19 (100)	C10—C11—C12—C13	−0.2 (9)
O1ⁱ—Co1—O6—C23'	133 (2)	C11—C12—C13—C14	−3.1 (10)
O1—Co1—O6—C23'	−47 (2)	C12—C13—C14—C15	2.9 (10)
O2ⁱ—Co1—O6—C23'	45 (2)	C11—C10—C15—C14	−3.9 (8)
O2—Co1—O6—C23'	−135 (2)	C1—C10—C15—C14	178.1 (5)
O6ⁱ—Co1—O6—C23'	−74 (100)	C13—C14—C15—C10	0.7 (9)
Co1—O1—C1—C2	8.8 (7)	C7—O4—C16—O5	−1.4 (7)
Co1—O1—C1—C10	−173.2 (3)	C7—O4—C16—C17	−179.9 (3)
O1—C1—C2—C3	3.0 (8)	O5—C16—C17—C22	−9.3 (7)
C10—C1—C2—C3	−175.0 (4)	O4—C16—C17—C22	169.2 (4)
Co1—O2—C3—C2	−10.7 (6)	O5—C16—C17—C18	172.5 (5)
Co1—O2—C3—C4	168.4 (3)	O4—C16—C17—C18	−9.0 (6)
C1—C2—C3—O2	−1.9 (8)	C22—C17—C18—C19	−0.3 (7)
C1—C2—C3—C4	179.0 (4)	C16—C17—C18—C19	177.9 (4)
O2—C3—C4—C9	178.0 (4)	C17—C18—C19—C20	−0.7 (7)
C2—C3—C4—C9	−3.0 (7)	C18—C19—C20—C21	0.3 (8)
O2—C3—C4—C5	−2.6 (6)	C19—C20—C21—C22	1.2 (8)
C2—C3—C4—C5	176.4 (4)	C20—C21—C22—C17	−2.2 (8)
C9—C4—C5—O3	−177.8 (4)	C18—C17—C22—C21	1.7 (7)
C3—C4—C5—O3	2.7 (7)	C16—C17—C22—C21	−176.6 (4)
C9—C4—C5—C6	2.8 (7)	C23'—O6—C23—C24	40 (2)
C3—C4—C5—C6	−176.6 (4)	Co1—O6—C23—C24	−79 (2)
O3—C5—C6—C7	179.4 (4)	C23—O6—C23'—C24'	−40 (4)
C4—C5—C6—C7	−1.2 (7)	Co1—O6—C23'—C24'	59 (5)
C5—C6—C7—C8	−2.0 (8)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.76	2.489 (4)	147
O6—H6···O3ⁱⁱ	0.85	2.02	2.855 (4)	168

Symmetry code: (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Co(C₂₂H₁₅O₅)₂(C₂H₆O)₂]
M_r	869.75
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.2068 (9), 9.4298 (12), 16.5511 (19)
α, β, γ (°)	106.358 (1), 95.431 (2), 90.920 (1)
V (Å³)	1073.3 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.38 × 0.15 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.844, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	5612, 3716, 1953
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.161, 0.95
No. of reflections	3716
No. of parameters	296
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.39

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—O1	2.015 (2)	Co1—O6	2.184 (4)
Co1—O2	2.033 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.76	2.489 (4)	147
O6—H6···O3ⁱ	0.85	2.02	2.855 (4)	168

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

Financial support for this work by the Program for Tackling Key Science & Technology of Shaanxi Province (2008K08-04) and the Specific Innovation Project for Important Science & Technology of Shaanxi Province (2008ZDKG-04) are gratefully acknowledged.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, L., Fang, R.-Q., Xue, J.-Y., Xiao, Z.-P., Tan, S.-H. & Zhu, H.-L. (2008). Aust. J. Chem. 61, 288–296. Web of Science CSD CrossRef CAS Google Scholar

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Volume 66| Part 8| August 2010| Pages m1038-m1039

https://doi.org/10.1107/S1600536810029776

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis[4-(2-benzoyl-1-oxidoethen­yl)-3-hy­dr­oxy­phenyl benzoato]di­ethano­l­cobalt(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[4-(2-benzoyl-1-oxidoethenyl)-3-hydroxyphenyl benzoato]diethanolcobalt(II)