Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045229/bg2101sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045229/bg2101Isup2.hkl |
CCDC reference: 663612
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- R factor = 0.056
- wR factor = 0.215
- Data-to-parameter ratio = 15.7
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) 3000 Deg. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1 (2) 1.90 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
3-(4-Carboxyphenoxy)propionic acid [3-(p-CPOPH2)] has been reported previously (Gao & Ng, 2006). In our previous work, the cobalt(II) complex of 3-(p-CPOPH2) has been characterized by X-ray crystallography (Xiao et al., 2006).
The title complex was prepared by the addition of cobalt(II) acetate trihydrate (10 mmol), pyridine (1 ml) and 3-(p-CPOPH2) (15 mmol) to a H2O/MeOH (v/v = 1:1) solution. Red crystals were obtained from the filtered solution at room temperature over several days. CH&N analysis. Calc. for C50H48N2O20Co: C 56.88, H 4.58, N 2.65%. Found: C 56.89, H 4.56, N 2.66%.
The H atoms were placed in calculated positions with C—H = 0.93 or 0.97 Å and Uiso(H) = 1.2Ueq (C) and were included in the refinement in the riding model approximation. The H atoms of hydroxyl groups were located in difference Fourier maps and refined with the O—H distance restrained to 0.85 (1) Å and Uiso(H) = 1.5Ueq(O).
Our studies have addressed the metal derivatives of carboxyphenoxypropionic acids. 3-(4-carboxylatophenoxy)propionic acid [3-(p-CPOPH2)] is a potential flexible multidentated ligand which could be used as a terminal ligand or a bridging ligand with different coordination modes when coordinated to various metal ions. In addition to its versatile coordination modes, 3-(4-carboxylatophenoxy)propionic acid may take part in hydrogen-bonding interactions by functioning as either a hydrogen-bond donor or acceptor (Gao & Ng, 2006). Recently, we have reported the structure of a dinuclear cobalt(II) complex incorporating 3-(4-carboxylatophenoxy)propionate groups, namely [Co2(C10H8O5)2(H2O)8].4H2O, (I) (Xiao et al., 2006).
In contrast to (I), the title compound is a mononuclear complex (Fig. 1), in which the Co atom lies on a centre of symmetry and displays a distorted octahedral geometry involving two O atoms of the 3-(4-carboxylatophenoxy)propionate groups, two O atoms of the 3-(4-carboxyphenoxy)propionic acid groups and two N atoms of two pyridine ligands. The average Co—O(carbonyl) bond length is 2.094 (2) Å, which is somewhat longer than the corresponding value in (I), 2.038 (3) Å. Furthermore, a two-dimensional supramolecular layer is constructed via π–π stacking interactions between the pyridine rings [centroid-centroid distance: 3.589 (3) Å] and hydrogen-bonding interactions (Table 2). There is, in additiom, a strong intramolecular H-bond (first entry in Table 2 and Fig. 1), linking the two independent, coordinated carboxylate groups.
3-(4-Carboxyphenoxy)propionic acid [3-(p-CPOPH2)] has been reported previously (Gao & Ng, 2006). In our previous work, the cobalt(II) complex of 3-(p-CPOPH2) has been characterized by X-ray crystallography (Xiao et al., 2006).
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. Molecular structure of the title compound with 30% probability ellipsoid for the non-H atoms. Dashed lines indicate O—H···O hydrogen bonds. [Symmetry code: (i) -x + 1,-y + 1,-z] |
[Co(C10H9O5)2(C10H10O5)2(C5H5N)2] | Z = 1 |
Mr = 1055.83 | F(000) = 549 |
Triclinic, P1 | Dx = 1.483 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2621 (17) Å | Cell parameters from 7199 reflections |
b = 8.7358 (17) Å | θ = 3.1–27.4° |
c = 17.502 (4) Å | µ = 0.45 mm−1 |
α = 76.58 (3)° | T = 295 K |
β = 76.53 (3)° | Block, red |
γ = 78.94 (3)° | 0.38 × 0.25 × 0.19 mm |
V = 1182.2 (5) Å3 |
Rigaku R-AXIS RAPID diffractometer | 5356 independent reflections |
Radiation source: fine-focus sealed tube | 2748 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −11→11 |
Tmin = 0.848, Tmax = 0.920 | l = −22→22 |
11688 measured reflections |
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)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.215 | w = 1/[σ2(Fo2) + (0.116P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
5356 reflections | Δρmax = 0.52 e Å−3 |
341 parameters | Δρmin = −0.98 e Å−3 |
3 restraints | Extinction correction: SHELXL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.010 (3) |
[Co(C10H9O5)2(C10H10O5)2(C5H5N)2] | γ = 78.94 (3)° |
Mr = 1055.83 | V = 1182.2 (5) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.2621 (17) Å | Mo Kα radiation |
b = 8.7358 (17) Å | µ = 0.45 mm−1 |
c = 17.502 (4) Å | T = 295 K |
α = 76.58 (3)° | 0.38 × 0.25 × 0.19 mm |
β = 76.53 (3)° |
Rigaku R-AXIS RAPID diffractometer | 5356 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2748 reflections with I > 2σ(I) |
Tmin = 0.848, Tmax = 0.920 | Rint = 0.038 |
11688 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 3 restraints |
wR(F2) = 0.215 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.52 e Å−3 |
5356 reflections | Δρmin = −0.98 e Å−3 |
341 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 | ||
Co1 | 0.5000 | 0.5000 | 0.0000 | 0.0479 (3) | |
O1 | 0.5675 (4) | 0.1351 (3) | 0.13958 (16) | 0.0678 (8) | |
O2 | 0.5516 (4) | 0.3988 (3) | 0.11210 (15) | 0.0602 (7) | |
O3 | 0.2880 (3) | 0.1751 (3) | 0.29858 (16) | 0.0637 (7) | |
O4 | −0.1451 (4) | −0.3393 (4) | 0.52659 (19) | 0.0735 (9) | |
H20 | −0.224 (5) | −0.394 (6) | 0.551 (3) | 0.110* | |
O5 | −0.3392 (4) | −0.1726 (4) | 0.46859 (19) | 0.0738 (8) | |
O6 | 0.3566 (4) | 0.6826 (3) | 0.05983 (17) | 0.0659 (8) | |
O7 | 0.3480 (5) | 0.9294 (4) | −0.00646 (19) | 0.0822 (10) | |
H30 | 0.380 (8) | 0.906 (7) | −0.0533 (16) | 0.123* | |
O8 | 0.0279 (3) | 0.8049 (3) | 0.19057 (16) | 0.0630 (7) | |
O9 | −0.4260 (4) | 0.3466 (4) | 0.45047 (19) | 0.0741 (9) | |
H10 | −0.509 (5) | 0.297 (6) | 0.474 (3) | 0.111* | |
O10 | −0.6187 (4) | 0.5077 (3) | 0.38703 (18) | 0.0680 (8) | |
N1 | 0.2787 (4) | 0.3899 (3) | 0.02698 (19) | 0.0514 (7) | |
C1 | 0.3358 (5) | 0.8248 (5) | 0.0582 (2) | 0.0536 (9) | |
C2 | 0.2917 (5) | 0.8889 (5) | 0.1345 (2) | 0.0619 (11) | |
H1 | 0.3946 | 0.9019 | 0.1484 | 0.074* | |
H2 | 0.2248 | 0.9931 | 0.1252 | 0.074* | |
C3 | 0.1959 (5) | 0.7840 (5) | 0.2039 (2) | 0.0606 (10) | |
H3 | 0.2468 | 0.6736 | 0.2066 | 0.073* | |
H4 | 0.1957 | 0.8142 | 0.2539 | 0.073* | |
C4 | −0.0854 (5) | 0.7190 (5) | 0.2447 (2) | 0.0553 (9) | |
C5 | −0.0460 (5) | 0.5970 (5) | 0.3068 (2) | 0.0616 (10) | |
H5 | 0.0641 | 0.5694 | 0.3147 | 0.074* | |
C6 | −0.1713 (5) | 0.5166 (5) | 0.3568 (2) | 0.0611 (10) | |
H6 | −0.1447 | 0.4352 | 0.3987 | 0.073* | |
C7 | −0.3353 (5) | 0.5547 (4) | 0.3459 (2) | 0.0546 (9) | |
C8 | −0.3740 (5) | 0.6792 (5) | 0.2833 (2) | 0.0612 (10) | |
H8 | −0.4843 | 0.7080 | 0.2756 | 0.073* | |
C9 | −0.2496 (5) | 0.7586 (5) | 0.2333 (2) | 0.0613 (10) | |
H9 | −0.2757 | 0.8399 | 0.1913 | 0.074* | |
C10 | −0.4689 (5) | 0.4657 (5) | 0.3978 (2) | 0.0576 (10) | |
C11 | 0.5552 (4) | 0.2669 (5) | 0.1590 (2) | 0.0516 (9) | |
C12 | 0.5483 (6) | 0.2669 (5) | 0.2461 (2) | 0.0660 (11) | |
H11 | 0.6623 | 0.2550 | 0.2546 | 0.079* | |
H12 | 0.4909 | 0.3692 | 0.2576 | 0.079* | |
C13 | 0.4605 (5) | 0.1377 (5) | 0.3044 (2) | 0.0625 (11) | |
H13 | 0.5077 | 0.0348 | 0.2906 | 0.075* | |
H14 | 0.4729 | 0.1349 | 0.3585 | 0.075* | |
C14 | 0.1814 (5) | 0.0733 (4) | 0.3434 (2) | 0.0531 (9) | |
C15 | 0.2274 (5) | −0.0672 (5) | 0.3948 (2) | 0.0572 (10) | |
H15 | 0.3389 | −0.0980 | 0.4003 | 0.069* | |
C16 | 0.1063 (5) | −0.1611 (5) | 0.4377 (2) | 0.0568 (10) | |
H16 | 0.1377 | −0.2556 | 0.4717 | 0.068* | |
C17 | −0.0601 (5) | −0.1172 (4) | 0.4310 (2) | 0.0536 (9) | |
C18 | −0.1041 (5) | 0.0249 (5) | 0.3791 (3) | 0.0658 (11) | |
H18 | −0.2156 | 0.0566 | 0.3736 | 0.079* | |
C19 | 0.0148 (5) | 0.1173 (5) | 0.3365 (3) | 0.0658 (11) | |
H19 | −0.0166 | 0.2115 | 0.3022 | 0.079* | |
C20 | −0.1901 (5) | −0.2154 (5) | 0.4776 (2) | 0.0549 (9) | |
C21 | 0.2354 (5) | 0.3318 (5) | −0.0281 (3) | 0.0614 (10) | |
H21 | 0.3072 | 0.3351 | −0.0778 | 0.074* | |
C22 | 0.0891 (6) | 0.2669 (5) | −0.0151 (3) | 0.0723 (12) | |
H22 | 0.0641 | 0.2259 | −0.0548 | 0.087* | |
C23 | −0.0170 (6) | 0.2644 (6) | 0.0567 (3) | 0.0810 (14) | |
H23 | −0.1169 | 0.2223 | 0.0671 | 0.097* | |
C24 | 0.0248 (6) | 0.3247 (7) | 0.1140 (3) | 0.0831 (14) | |
H24 | −0.0473 | 0.3250 | 0.1635 | 0.100* | |
C25 | 0.1731 (5) | 0.3845 (5) | 0.0981 (2) | 0.0662 (11) | |
H25 | 0.2014 | 0.4227 | 0.1379 | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0527 (5) | 0.0506 (4) | 0.0412 (4) | −0.0108 (3) | −0.0115 (3) | −0.0058 (3) |
O1 | 0.095 (2) | 0.0616 (16) | 0.0466 (16) | −0.0208 (15) | −0.0101 (15) | −0.0057 (13) |
O2 | 0.0734 (19) | 0.0650 (16) | 0.0448 (15) | −0.0213 (14) | −0.0214 (13) | 0.0030 (12) |
O3 | 0.0584 (17) | 0.0690 (17) | 0.0536 (17) | −0.0136 (13) | −0.0069 (13) | 0.0071 (13) |
O4 | 0.074 (2) | 0.079 (2) | 0.0613 (19) | −0.0216 (16) | −0.0135 (16) | 0.0065 (16) |
O5 | 0.063 (2) | 0.083 (2) | 0.072 (2) | −0.0164 (15) | −0.0152 (16) | −0.0020 (16) |
O6 | 0.077 (2) | 0.0581 (16) | 0.0602 (18) | −0.0128 (14) | −0.0041 (15) | −0.0130 (13) |
O7 | 0.122 (3) | 0.0633 (18) | 0.0555 (19) | −0.0167 (18) | −0.0097 (19) | −0.0052 (15) |
O8 | 0.0549 (17) | 0.0801 (18) | 0.0533 (17) | −0.0182 (14) | −0.0148 (13) | −0.0007 (13) |
O9 | 0.070 (2) | 0.081 (2) | 0.066 (2) | −0.0215 (16) | −0.0178 (16) | 0.0090 (16) |
O10 | 0.0594 (19) | 0.0753 (18) | 0.0654 (19) | −0.0128 (14) | −0.0149 (15) | −0.0013 (14) |
N1 | 0.0548 (19) | 0.0526 (17) | 0.0468 (18) | −0.0099 (14) | −0.0149 (14) | −0.0030 (13) |
C1 | 0.047 (2) | 0.058 (2) | 0.057 (2) | −0.0130 (17) | −0.0123 (17) | −0.0068 (18) |
C2 | 0.069 (3) | 0.064 (2) | 0.060 (3) | −0.022 (2) | −0.011 (2) | −0.018 (2) |
C3 | 0.061 (3) | 0.076 (3) | 0.051 (2) | −0.014 (2) | −0.0150 (19) | −0.018 (2) |
C4 | 0.057 (2) | 0.066 (2) | 0.047 (2) | −0.0130 (19) | −0.0110 (18) | −0.0137 (18) |
C5 | 0.054 (2) | 0.077 (3) | 0.055 (2) | −0.008 (2) | −0.0215 (19) | −0.004 (2) |
C6 | 0.067 (3) | 0.069 (2) | 0.050 (2) | −0.014 (2) | −0.021 (2) | −0.0037 (19) |
C7 | 0.062 (3) | 0.058 (2) | 0.048 (2) | −0.0097 (18) | −0.0177 (18) | −0.0104 (17) |
C8 | 0.057 (2) | 0.069 (2) | 0.059 (3) | −0.0116 (19) | −0.020 (2) | −0.006 (2) |
C9 | 0.060 (3) | 0.069 (2) | 0.052 (2) | −0.012 (2) | −0.0165 (19) | 0.0013 (19) |
C10 | 0.062 (3) | 0.069 (2) | 0.047 (2) | −0.014 (2) | −0.0146 (19) | −0.0124 (19) |
C11 | 0.044 (2) | 0.069 (2) | 0.043 (2) | −0.0153 (17) | −0.0109 (16) | −0.0061 (18) |
C12 | 0.075 (3) | 0.086 (3) | 0.042 (2) | −0.029 (2) | −0.017 (2) | −0.0023 (19) |
C13 | 0.064 (3) | 0.084 (3) | 0.038 (2) | −0.017 (2) | −0.0119 (18) | −0.0014 (18) |
C14 | 0.057 (2) | 0.061 (2) | 0.040 (2) | −0.0092 (18) | −0.0070 (17) | −0.0078 (16) |
C15 | 0.055 (2) | 0.070 (2) | 0.042 (2) | −0.0090 (19) | −0.0146 (17) | 0.0022 (17) |
C16 | 0.064 (3) | 0.061 (2) | 0.042 (2) | −0.0092 (19) | −0.0149 (18) | 0.0023 (17) |
C17 | 0.060 (2) | 0.062 (2) | 0.038 (2) | −0.0124 (18) | −0.0089 (17) | −0.0068 (16) |
C18 | 0.054 (2) | 0.079 (3) | 0.061 (3) | −0.006 (2) | −0.018 (2) | −0.001 (2) |
C19 | 0.062 (3) | 0.067 (2) | 0.059 (3) | −0.005 (2) | −0.014 (2) | 0.0053 (19) |
C20 | 0.052 (2) | 0.066 (2) | 0.047 (2) | −0.0067 (19) | −0.0114 (18) | −0.0107 (18) |
C21 | 0.061 (3) | 0.068 (2) | 0.060 (3) | −0.017 (2) | −0.013 (2) | −0.013 (2) |
C22 | 0.062 (3) | 0.088 (3) | 0.075 (3) | −0.019 (2) | −0.021 (2) | −0.020 (2) |
C23 | 0.058 (3) | 0.104 (4) | 0.087 (4) | −0.032 (3) | −0.023 (3) | −0.003 (3) |
C24 | 0.053 (3) | 0.123 (4) | 0.068 (3) | −0.026 (3) | −0.004 (2) | −0.005 (3) |
C25 | 0.060 (3) | 0.092 (3) | 0.046 (2) | −0.017 (2) | −0.010 (2) | −0.009 (2) |
Co1—O2 | 2.062 (3) | C6—C7 | 1.379 (5) |
Co1—O6 | 2.125 (3) | C6—H6 | 0.9300 |
Co1—N1 | 2.133 (3) | C7—C8 | 1.401 (5) |
Co1—O2i | 2.062 (3) | C7—C10 | 1.477 (5) |
Co1—O6i | 2.125 (3) | C8—C9 | 1.369 (5) |
Co1—N1i | 2.133 (3) | C8—H8 | 0.9300 |
O1—C11 | 1.254 (5) | C9—H9 | 0.9300 |
O2—C11 | 1.250 (4) | C11—C12 | 1.512 (5) |
O3—C14 | 1.355 (4) | C12—C13 | 1.508 (5) |
O3—C13 | 1.422 (5) | C12—H11 | 0.9700 |
O4—C20 | 1.268 (5) | C12—H12 | 0.9700 |
O4—H20 | 0.86 (5) | C13—H13 | 0.9700 |
O5—C20 | 1.253 (5) | C13—H14 | 0.9700 |
O6—C1 | 1.215 (4) | C14—C19 | 1.382 (6) |
O7—C1 | 1.276 (5) | C14—C15 | 1.388 (5) |
O7—H30 | 0.86 (3) | C15—C16 | 1.384 (5) |
O8—C4 | 1.365 (4) | C15—H15 | 0.9300 |
O8—C3 | 1.432 (5) | C16—C17 | 1.379 (5) |
O9—C10 | 1.274 (5) | C16—H16 | 0.9300 |
O9—H10 | 0.85 (5) | C17—C18 | 1.398 (5) |
O10—C10 | 1.266 (5) | C17—C20 | 1.475 (5) |
N1—C21 | 1.331 (5) | C18—C19 | 1.363 (6) |
N1—C25 | 1.340 (5) | C18—H18 | 0.9300 |
C1—C2 | 1.507 (6) | C19—H19 | 0.9300 |
C2—C3 | 1.502 (5) | C21—C22 | 1.382 (6) |
C2—H1 | 0.9700 | C21—H21 | 0.9300 |
C2—H2 | 0.9700 | C22—C23 | 1.352 (7) |
C3—H3 | 0.9700 | C22—H22 | 0.9300 |
C3—H4 | 0.9700 | C23—C24 | 1.371 (7) |
C4—C9 | 1.383 (6) | C23—H23 | 0.9300 |
C4—C5 | 1.384 (5) | C24—C25 | 1.367 (6) |
C5—C6 | 1.379 (5) | C24—H24 | 0.9300 |
C5—H5 | 0.9300 | C25—H25 | 0.9300 |
O2—Co1—O2i | 180.00 (16) | C8—C9—H9 | 119.7 |
O2—Co1—O6 | 82.86 (12) | C4—C9—H9 | 119.7 |
O2—Co1—O6i | 97.14 (12) | O10—C10—O9 | 123.0 (4) |
O6—Co1—O6i | 180.00 (14) | O10—C10—C7 | 119.3 (4) |
O2—Co1—N1i | 88.77 (11) | O9—C10—C7 | 117.7 (4) |
O6—Co1—N1i | 91.89 (11) | O2—C11—O1 | 125.5 (4) |
O2—Co1—N1 | 91.23 (11) | O2—C11—C12 | 116.9 (4) |
O6—Co1—N1 | 88.11 (11) | O1—C11—C12 | 117.6 (3) |
N1i—Co1—N1 | 180.00 (17) | C13—C12—C11 | 114.3 (3) |
O2i—Co1—O6i | 82.86 (12) | C13—C12—H11 | 108.7 |
O2i—Co1—N1i | 91.23 (11) | C11—C12—H11 | 108.7 |
O6i—Co1—N1i | 88.11 (11) | C13—C12—H12 | 108.7 |
O6i—Co1—N1 | 91.89 (11) | C11—C12—H12 | 108.7 |
O2i—Co1—N1 | 88.77 (11) | H11—C12—H12 | 107.6 |
O2i—Co1—O6 | 97.14 (12) | O3—C13—C12 | 106.5 (3) |
C11—O2—Co1 | 139.0 (2) | O3—C13—H13 | 110.4 |
C14—O3—C13 | 118.3 (3) | C12—C13—H13 | 110.4 |
C20—O4—H20 | 114 (4) | O3—C13—H14 | 110.4 |
C1—O6—Co1 | 143.5 (3) | C12—C13—H14 | 110.4 |
C1—O7—H30 | 123 (4) | H13—C13—H14 | 108.6 |
C4—O8—C3 | 118.5 (3) | O3—C14—C19 | 115.7 (3) |
C10—O9—H10 | 111 (4) | O3—C14—C15 | 125.1 (4) |
C21—N1—C25 | 117.3 (3) | C19—C14—C15 | 119.2 (3) |
C21—N1—Co1 | 121.0 (3) | C16—C15—C14 | 119.6 (4) |
C25—N1—Co1 | 121.6 (3) | C16—C15—H15 | 120.2 |
O6—C1—O7 | 123.6 (4) | C14—C15—H15 | 120.2 |
O6—C1—C2 | 121.0 (4) | C17—C16—C15 | 121.3 (3) |
O7—C1—C2 | 115.4 (4) | C17—C16—H16 | 119.4 |
C3—C2—C1 | 113.5 (3) | C15—C16—H16 | 119.4 |
C3—C2—H1 | 108.9 | C16—C17—C18 | 118.3 (3) |
C1—C2—H1 | 108.9 | C16—C17—C20 | 121.5 (3) |
C3—C2—H2 | 108.9 | C18—C17—C20 | 120.2 (4) |
C1—C2—H2 | 108.9 | C19—C18—C17 | 120.6 (4) |
H1—C2—H2 | 107.7 | C19—C18—H18 | 119.7 |
O8—C3—C2 | 106.6 (3) | C17—C18—H18 | 119.7 |
O8—C3—H3 | 110.4 | C18—C19—C14 | 121.0 (4) |
C2—C3—H3 | 110.4 | C18—C19—H19 | 119.5 |
O8—C3—H4 | 110.4 | C14—C19—H19 | 119.5 |
C2—C3—H4 | 110.4 | O5—C20—O4 | 122.9 (4) |
H3—C3—H4 | 108.6 | O5—C20—C17 | 119.3 (4) |
O8—C4—C9 | 115.4 (3) | O4—C20—C17 | 117.8 (4) |
O8—C4—C5 | 124.9 (4) | N1—C21—C22 | 123.3 (4) |
C9—C4—C5 | 119.7 (4) | N1—C21—H21 | 118.4 |
C6—C5—C4 | 119.5 (4) | C22—C21—H21 | 118.4 |
C6—C5—H5 | 120.2 | C23—C22—C21 | 118.5 (4) |
C4—C5—H5 | 120.2 | C23—C22—H22 | 120.7 |
C7—C6—C5 | 121.3 (4) | C21—C22—H22 | 120.7 |
C7—C6—H6 | 119.4 | C22—C23—C24 | 119.0 (4) |
C5—C6—H6 | 119.4 | C22—C23—H23 | 120.5 |
C6—C7—C8 | 118.7 (4) | C24—C23—H23 | 120.5 |
C6—C7—C10 | 121.4 (4) | C25—C24—C23 | 119.8 (4) |
C8—C7—C10 | 119.8 (4) | C25—C24—H24 | 120.1 |
C9—C8—C7 | 120.1 (4) | C23—C24—H24 | 120.1 |
C9—C8—H8 | 120.0 | N1—C25—C24 | 122.1 (4) |
C7—C8—H8 | 120.0 | N1—C25—H25 | 119.0 |
C8—C9—C4 | 120.7 (4) | C24—C25—H25 | 119.0 |
O6—Co1—O2—C11 | 133.4 (4) | C6—C7—C10—O10 | 178.0 (4) |
O6i—Co1—O2—C11 | −46.6 (4) | C8—C7—C10—O10 | −2.9 (6) |
N1i—Co1—O2—C11 | −134.6 (4) | C6—C7—C10—O9 | −3.8 (6) |
N1—Co1—O2—C11 | 45.4 (4) | C8—C7—C10—O9 | 175.3 (4) |
O2—Co1—O6—C1 | 125.5 (5) | Co1—O2—C11—O1 | 20.6 (6) |
O2i—Co1—O6—C1 | −54.5 (5) | Co1—O2—C11—C12 | −160.9 (3) |
N1i—Co1—O6—C1 | 37.0 (5) | O2—C11—C12—C13 | 148.0 (4) |
N1—Co1—O6—C1 | −143.0 (5) | O1—C11—C12—C13 | −33.4 (6) |
O2—Co1—N1—C21 | −141.4 (3) | C14—O3—C13—C12 | 177.7 (3) |
O2i—Co1—N1—C21 | 38.6 (3) | C11—C12—C13—O3 | −67.6 (5) |
O6—Co1—N1—C21 | 135.8 (3) | C13—O3—C14—C19 | 178.8 (4) |
O6i—Co1—N1—C21 | −44.2 (3) | C13—O3—C14—C15 | −0.5 (6) |
O2—Co1—N1—C25 | 42.5 (3) | O3—C14—C15—C16 | 179.7 (4) |
O2i—Co1—N1—C25 | −137.5 (3) | C19—C14—C15—C16 | 0.5 (6) |
O6—Co1—N1—C25 | −40.3 (3) | C14—C15—C16—C17 | −0.6 (6) |
O6i—Co1—N1—C25 | 139.7 (3) | C15—C16—C17—C18 | 0.4 (6) |
Co1—O6—C1—O7 | 35.9 (7) | C15—C16—C17—C20 | −178.9 (4) |
Co1—O6—C1—C2 | −144.6 (4) | C16—C17—C18—C19 | −0.1 (6) |
O6—C1—C2—C3 | −28.8 (6) | C20—C17—C18—C19 | 179.3 (4) |
O7—C1—C2—C3 | 150.8 (4) | C17—C18—C19—C14 | 0.0 (7) |
C4—O8—C3—C2 | 178.5 (3) | O3—C14—C19—C18 | −179.5 (4) |
C1—C2—C3—O8 | −74.8 (4) | C15—C14—C19—C18 | −0.2 (6) |
C3—O8—C4—C9 | 172.7 (3) | C16—C17—C20—O5 | −178.7 (4) |
C3—O8—C4—C5 | −8.8 (6) | C18—C17—C20—O5 | 2.0 (6) |
O8—C4—C5—C6 | −178.7 (4) | C16—C17—C20—O4 | 2.6 (6) |
C9—C4—C5—C6 | −0.2 (6) | C18—C17—C20—O4 | −176.8 (4) |
C4—C5—C6—C7 | 0.5 (6) | C25—N1—C21—C22 | −0.3 (6) |
C5—C6—C7—C8 | −1.0 (6) | Co1—N1—C21—C22 | −176.5 (3) |
C5—C6—C7—C10 | 178.1 (4) | N1—C21—C22—C23 | 1.1 (7) |
C6—C7—C8—C9 | 1.3 (6) | C21—C22—C23—C24 | −0.5 (8) |
C10—C7—C8—C9 | −177.8 (4) | C22—C23—C24—C25 | −0.8 (8) |
C7—C8—C9—C4 | −1.1 (6) | C21—N1—C25—C24 | −1.1 (6) |
O8—C4—C9—C8 | 179.2 (4) | Co1—N1—C25—C24 | 175.1 (4) |
C5—C4—C9—C8 | 0.6 (6) | C23—C24—C25—N1 | 1.6 (8) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H30···O1i | 0.86 (3) | 1.58 (4) | 2.436 (4) | 178 (7) |
O4—H20···O10ii | 0.86 (5) | 1.79 (5) | 2.637 (4) | 173 (6) |
O9—H10···O5ii | 0.85 (5) | 1.79 (5) | 2.633 (4) | 172 (6) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x−1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Co(C10H9O5)2(C10H10O5)2(C5H5N)2] |
Mr | 1055.83 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 8.2621 (17), 8.7358 (17), 17.502 (4) |
α, β, γ (°) | 76.58 (3), 76.53 (3), 78.94 (3) |
V (Å3) | 1182.2 (5) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.45 |
Crystal size (mm) | 0.38 × 0.25 × 0.19 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.848, 0.920 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11688, 5356, 2748 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.215, 1.07 |
No. of reflections | 5356 |
No. of parameters | 341 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.52, −0.98 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).
Co1—O2 | 2.062 (3) | Co1—N1 | 2.133 (3) |
Co1—O6 | 2.125 (3) | ||
O2—Co1—O6 | 82.86 (12) | O6—Co1—N1 | 88.11 (11) |
O2—Co1—N1 | 91.23 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H30···O1i | 0.86 (3) | 1.58 (4) | 2.436 (4) | 178 (7) |
O4—H20···O10ii | 0.86 (5) | 1.79 (5) | 2.637 (4) | 173 (6) |
O9—H10···O5ii | 0.85 (5) | 1.79 (5) | 2.633 (4) | 172 (6) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x−1, −y, −z+1. |
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Our studies have addressed the metal derivatives of carboxyphenoxypropionic acids. 3-(4-carboxylatophenoxy)propionic acid [3-(p-CPOPH2)] is a potential flexible multidentated ligand which could be used as a terminal ligand or a bridging ligand with different coordination modes when coordinated to various metal ions. In addition to its versatile coordination modes, 3-(4-carboxylatophenoxy)propionic acid may take part in hydrogen-bonding interactions by functioning as either a hydrogen-bond donor or acceptor (Gao & Ng, 2006). Recently, we have reported the structure of a dinuclear cobalt(II) complex incorporating 3-(4-carboxylatophenoxy)propionate groups, namely [Co2(C10H8O5)2(H2O)8].4H2O, (I) (Xiao et al., 2006).
In contrast to (I), the title compound is a mononuclear complex (Fig. 1), in which the Co atom lies on a centre of symmetry and displays a distorted octahedral geometry involving two O atoms of the 3-(4-carboxylatophenoxy)propionate groups, two O atoms of the 3-(4-carboxyphenoxy)propionic acid groups and two N atoms of two pyridine ligands. The average Co—O(carbonyl) bond length is 2.094 (2) Å, which is somewhat longer than the corresponding value in (I), 2.038 (3) Å. Furthermore, a two-dimensional supramolecular layer is constructed via π–π stacking interactions between the pyridine rings [centroid-centroid distance: 3.589 (3) Å] and hydrogen-bonding interactions (Table 2). There is, in additiom, a strong intramolecular H-bond (first entry in Table 2 and Fig. 1), linking the two independent, coordinated carboxylate groups.