metal-organic compounds
Triaqua(cyclohex-4-ene-1,2-dicarboxylato-κO1)(1,10-phenanthroline-κ2N,N′)cobalt(II)
aCollege of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin, Guangxi 541004, People's Republic of China
*Correspondence e-mail: huangfp2006@163.com
In the title compound, [Co(C8H8O4)(C12H8N2)(H2O)3], the CoII atom is coordinated by two N atoms from a bidentate 1,10-phenanthroline ligand, one O atom from a monodentate 4-cyclohexene-1,2-dicarboxylate ligand and three water O atoms in a distorted octahedral geometry. The mononuclear molecules are engaged in extensive intra- and intermolecular O—H⋯O hydrogen-bonding interactions and π–π stacking interactions [centroid–centroid distance = 3.784 (3) Å], forming a three-dimensional supramolecular network.
Related literature
For background to compounds with metal-organic framework structures, see: Huang et al. (2010); Ockwig et al. (2005); Rao et al. (2004). For a description of the Cambridge Structural Database (CSD), see: Allen (2002). For 4-cyclohexene-1,2-dicarboxylates, see: Kim et al. (2004); Lee et al. (2006). For related structures, see: Baruah et al. (2007); Hou et al. (2007); Zhang et al. (2008).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1998); cell SAINT (Bruker, 1998); data reduction: SAINT; 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
10.1107/S160053681204024X/zq2181sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681204024X/zq2181Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681204024X/zq2181Isup3.cdx
For the preparation of the title complex, cis-4-cyclohexene-1,2-dicarboxylate acid (0.085 g, 0.5 mmol), Co(NO3)2.6H2O (0.12 g, 0.5 mmol), phen (0.10 g, 0.5 mmol) and KHCO3 (0.10 g, 1 mmol) were dissolved in a water/ethanol solution (20 ml, 1:1). The solution was stirred for 3 h at room temperature and filtered. Red block-shaped crystals were obtained from the filtrate after 4 d.
H atoms of water molecules were located in a difference Fourier map and refined with distance restraints of O—H = 0.85 (2) Å and H···H = 1.39 (2) Å. All other H atoms were positoned geometrically and refined using a riding model, with C—H = 0.93 Å for C—Haromatic and C—H = 0.97 Å for C—Haliphatic [Uiso(H) = 1.2Ueq(C)] .
Data collection: SMART (Bruker, 1998); cell
SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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).Fig. 1. The asymmetric unit of the title compound with the atom-numbering scheme and displacement ellipsoids at the 30% probability level. | |
Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dotted lines. |
[Co(C8H8O4)(C12H8N2)(H2O)3] | F(000) = 956 |
Mr = 461.33 | Dx = 1.538 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2567 reflections |
a = 8.1730 (16) Å | θ = 1.5–25.3° |
b = 20.210 (4) Å | µ = 0.91 mm−1 |
c = 12.068 (2) Å | T = 293 K |
β = 91.44 (3)° | Block, red |
V = 1992.7 (7) Å3 | 0.40 × 0.20 × 0.08 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3606 independent reflections |
Radiation source: fine-focus sealed tube | 2982 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
phi and ω scans | θmax = 25.3°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.801, Tmax = 0.945 | k = −24→24 |
15996 measured reflections | l = −14→14 |
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) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0338P)2 + 5.P] where P = (Fo2 + 2Fc2)/3 |
3606 reflections | (Δ/σ)max < 0.001 |
295 parameters | Δρmax = 0.28 e Å−3 |
9 restraints | Δρmin = −0.34 e Å−3 |
[Co(C8H8O4)(C12H8N2)(H2O)3] | V = 1992.7 (7) Å3 |
Mr = 461.33 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.1730 (16) Å | µ = 0.91 mm−1 |
b = 20.210 (4) Å | T = 293 K |
c = 12.068 (2) Å | 0.40 × 0.20 × 0.08 mm |
β = 91.44 (3)° |
Bruker SMART CCD area-detector diffractometer | 3606 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2982 reflections with I > 2σ(I) |
Tmin = 0.801, Tmax = 0.945 | Rint = 0.073 |
15996 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 9 restraints |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.28 e Å−3 |
3606 reflections | Δρmin = −0.34 e Å−3 |
295 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 | 0.23393 (6) | 0.53534 (3) | 0.19466 (4) | 0.02844 (17) | |
C1 | 0.3182 (5) | 0.67605 (19) | 0.1389 (3) | 0.0319 (9) | |
C2 | 0.4497 (5) | 0.71600 (19) | 0.0814 (3) | 0.0327 (9) | |
H2A | 0.4249 | 0.7143 | 0.0016 | 0.039* | |
C3 | 0.4475 (6) | 0.7890 (2) | 0.1160 (4) | 0.0463 (12) | |
H3A | 0.5051 | 0.8151 | 0.0620 | 0.056* | |
H3B | 0.3352 | 0.8045 | 0.1169 | 0.056* | |
C4 | 0.5250 (6) | 0.7988 (2) | 0.2267 (5) | 0.0567 (14) | |
H4A | 0.5006 | 0.8372 | 0.2655 | 0.068* | |
C5 | 0.6267 (6) | 0.7561 (3) | 0.2732 (4) | 0.0545 (14) | |
H5C | 0.6676 | 0.7657 | 0.3440 | 0.065* | |
C6 | 0.6815 (5) | 0.6932 (2) | 0.2206 (4) | 0.0400 (11) | |
H6C | 0.6419 | 0.6560 | 0.2632 | 0.048* | |
H6D | 0.8001 | 0.6916 | 0.2228 | 0.048* | |
C7 | 0.6202 (5) | 0.68620 (19) | 0.1002 (3) | 0.0319 (9) | |
H7C | 0.6947 | 0.7123 | 0.0553 | 0.038* | |
C8 | 0.6262 (5) | 0.61588 (19) | 0.0556 (3) | 0.0305 (9) | |
C9 | 0.3023 (5) | 0.5544 (2) | 0.4478 (3) | 0.0387 (10) | |
H9A | 0.3474 | 0.5952 | 0.4298 | 0.046* | |
C10 | 0.3035 (6) | 0.5346 (2) | 0.5592 (4) | 0.0460 (12) | |
H10A | 0.3491 | 0.5619 | 0.6138 | 0.055* | |
C11 | 0.2385 (6) | 0.4760 (2) | 0.5869 (4) | 0.0446 (12) | |
H11A | 0.2392 | 0.4628 | 0.6608 | 0.054* | |
C12 | 0.1695 (5) | 0.4345 (2) | 0.5047 (3) | 0.0369 (10) | |
C13 | 0.0959 (6) | 0.3723 (2) | 0.5252 (4) | 0.0446 (11) | |
H13A | 0.0915 | 0.3568 | 0.5976 | 0.054* | |
C14 | 0.0322 (6) | 0.3351 (2) | 0.4419 (4) | 0.0457 (12) | |
H14A | −0.0140 | 0.2942 | 0.4577 | 0.055* | |
C15 | 0.0348 (5) | 0.3577 (2) | 0.3300 (3) | 0.0359 (10) | |
C16 | −0.0345 (5) | 0.3215 (2) | 0.2400 (4) | 0.0426 (11) | |
H16A | −0.0839 | 0.2807 | 0.2518 | 0.051* | |
C17 | −0.0280 (5) | 0.3472 (2) | 0.1365 (4) | 0.0429 (11) | |
H17A | −0.0732 | 0.3242 | 0.0764 | 0.051* | |
C18 | 0.0467 (5) | 0.4080 (2) | 0.1210 (3) | 0.0357 (10) | |
H18A | 0.0505 | 0.4246 | 0.0493 | 0.043* | |
C19 | 0.1057 (5) | 0.41830 (19) | 0.3069 (3) | 0.0295 (9) | |
C20 | 0.1743 (5) | 0.4581 (2) | 0.3947 (3) | 0.0306 (9) | |
N1 | 0.2392 (4) | 0.51715 (16) | 0.3679 (3) | 0.0312 (8) | |
N2 | 0.1127 (4) | 0.44351 (16) | 0.2022 (3) | 0.0295 (8) | |
O1 | 0.3622 (3) | 0.62360 (13) | 0.1889 (2) | 0.0315 (6) | |
O2 | 0.1735 (3) | 0.69566 (14) | 0.1286 (3) | 0.0439 (8) | |
O3 | 0.5410 (3) | 0.60345 (14) | −0.0292 (2) | 0.0382 (7) | |
O4 | 0.7164 (3) | 0.57339 (13) | 0.1038 (2) | 0.0356 (7) | |
O5 | 0.4681 (4) | 0.48671 (15) | 0.1938 (2) | 0.0349 (7) | |
O6 | 0.2453 (4) | 0.53756 (15) | 0.0198 (2) | 0.0334 (7) | |
O7 | 0.0207 (4) | 0.59085 (15) | 0.1985 (3) | 0.0378 (7) | |
H5A | 0.465 (6) | 0.4552 (16) | 0.147 (3) | 0.062 (17)* | |
H6A | 0.258 (5) | 0.5009 (13) | −0.015 (4) | 0.061 (17)* | |
H7A | 0.054 (5) | 0.6283 (14) | 0.174 (4) | 0.052 (15)* | |
H5B | 0.538 (5) | 0.5151 (17) | 0.172 (4) | 0.059 (17)* | |
H6B | 0.324 (4) | 0.5630 (16) | 0.000 (4) | 0.054 (16)* | |
H7B | −0.077 (3) | 0.584 (2) | 0.172 (4) | 0.059 (16)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0293 (3) | 0.0295 (3) | 0.0264 (3) | −0.0004 (2) | 0.0010 (2) | 0.0015 (2) |
C1 | 0.037 (3) | 0.025 (2) | 0.033 (2) | 0.0006 (18) | 0.0004 (18) | −0.0067 (18) |
C2 | 0.039 (2) | 0.028 (2) | 0.031 (2) | 0.0023 (18) | 0.0014 (18) | 0.0018 (18) |
C3 | 0.044 (3) | 0.027 (2) | 0.069 (3) | 0.001 (2) | 0.008 (2) | 0.004 (2) |
C4 | 0.053 (3) | 0.038 (3) | 0.080 (4) | 0.002 (2) | 0.005 (3) | −0.028 (3) |
C5 | 0.055 (3) | 0.058 (3) | 0.050 (3) | −0.009 (3) | −0.001 (2) | −0.030 (3) |
C6 | 0.039 (3) | 0.040 (3) | 0.040 (3) | −0.005 (2) | −0.005 (2) | −0.008 (2) |
C7 | 0.031 (2) | 0.031 (2) | 0.034 (2) | −0.0034 (18) | 0.0025 (18) | 0.0011 (18) |
C8 | 0.028 (2) | 0.030 (2) | 0.034 (2) | −0.0042 (18) | 0.0074 (18) | −0.0021 (18) |
C9 | 0.045 (3) | 0.038 (2) | 0.033 (2) | −0.005 (2) | 0.000 (2) | −0.0021 (19) |
C10 | 0.059 (3) | 0.047 (3) | 0.032 (2) | −0.002 (2) | −0.010 (2) | −0.010 (2) |
C11 | 0.057 (3) | 0.050 (3) | 0.027 (2) | 0.002 (2) | −0.003 (2) | 0.001 (2) |
C12 | 0.039 (3) | 0.042 (3) | 0.030 (2) | 0.002 (2) | 0.0023 (19) | 0.0049 (19) |
C13 | 0.054 (3) | 0.050 (3) | 0.030 (2) | −0.004 (2) | −0.001 (2) | 0.011 (2) |
C14 | 0.054 (3) | 0.043 (3) | 0.040 (3) | −0.009 (2) | 0.002 (2) | 0.011 (2) |
C15 | 0.035 (2) | 0.038 (2) | 0.035 (2) | −0.0007 (19) | −0.0006 (19) | 0.0013 (19) |
C16 | 0.040 (3) | 0.037 (3) | 0.051 (3) | −0.011 (2) | −0.001 (2) | 0.002 (2) |
C17 | 0.043 (3) | 0.049 (3) | 0.036 (3) | −0.012 (2) | −0.005 (2) | −0.004 (2) |
C18 | 0.038 (2) | 0.043 (3) | 0.026 (2) | −0.003 (2) | −0.0022 (18) | −0.0007 (19) |
C19 | 0.027 (2) | 0.033 (2) | 0.028 (2) | −0.0013 (17) | 0.0009 (17) | 0.0007 (17) |
C20 | 0.030 (2) | 0.035 (2) | 0.026 (2) | 0.0045 (18) | 0.0017 (17) | 0.0014 (18) |
N1 | 0.033 (2) | 0.0333 (19) | 0.0272 (19) | 0.0009 (15) | 0.0018 (15) | −0.0008 (15) |
N2 | 0.0291 (18) | 0.0335 (19) | 0.0261 (18) | −0.0026 (15) | 0.0024 (14) | −0.0007 (14) |
O1 | 0.0310 (15) | 0.0284 (15) | 0.0349 (16) | −0.0012 (12) | −0.0008 (12) | 0.0018 (12) |
O2 | 0.0292 (17) | 0.0342 (17) | 0.068 (2) | 0.0063 (13) | −0.0034 (15) | 0.0008 (15) |
O3 | 0.0409 (17) | 0.0386 (17) | 0.0349 (17) | 0.0004 (13) | −0.0023 (14) | −0.0103 (13) |
O4 | 0.0337 (16) | 0.0298 (16) | 0.0432 (18) | 0.0029 (13) | −0.0031 (13) | −0.0023 (13) |
O5 | 0.0360 (18) | 0.0356 (17) | 0.0329 (17) | 0.0033 (14) | 0.0010 (13) | −0.0023 (14) |
O6 | 0.0376 (18) | 0.0334 (17) | 0.0293 (16) | −0.0010 (14) | 0.0023 (12) | −0.0015 (14) |
O7 | 0.0280 (17) | 0.0381 (19) | 0.0474 (19) | 0.0029 (14) | 0.0000 (14) | 0.0003 (15) |
Co1—O1 | 2.071 (3) | C9—H9A | 0.9300 |
Co1—O7 | 2.074 (3) | C10—C11 | 1.345 (6) |
Co1—N2 | 2.107 (3) | C10—H10A | 0.9300 |
Co1—O6 | 2.115 (3) | C11—C12 | 1.407 (6) |
Co1—N1 | 2.122 (3) | C11—H11A | 0.9300 |
Co1—O5 | 2.152 (3) | C12—C20 | 1.412 (5) |
C1—O2 | 1.250 (5) | C12—C13 | 1.418 (6) |
C1—O1 | 1.268 (5) | C13—C14 | 1.348 (6) |
C1—C2 | 1.525 (6) | C13—H13A | 0.9300 |
C2—C7 | 1.530 (6) | C14—C15 | 1.427 (6) |
C2—C3 | 1.533 (6) | C14—H14A | 0.9300 |
C2—H2A | 0.9800 | C15—C19 | 1.387 (6) |
C3—C4 | 1.477 (7) | C15—C16 | 1.415 (6) |
C3—H3A | 0.9700 | C16—C17 | 1.355 (6) |
C3—H3B | 0.9700 | C16—H16A | 0.9300 |
C4—C5 | 1.315 (7) | C17—C18 | 1.386 (6) |
C4—H4A | 0.9300 | C17—H17A | 0.9300 |
C5—C6 | 1.494 (6) | C18—N2 | 1.319 (5) |
C5—H5C | 0.9300 | C18—H18A | 0.9300 |
C6—C7 | 1.531 (6) | C19—N2 | 1.364 (5) |
C6—H6C | 0.9700 | C19—C20 | 1.433 (5) |
C6—H6D | 0.9700 | C20—N1 | 1.349 (5) |
C7—C8 | 1.521 (5) | O5—H5A | 0.852 (19) |
C7—H7C | 0.9800 | O5—H5B | 0.854 (19) |
C8—O3 | 1.250 (5) | O6—H6A | 0.860 (19) |
C8—O4 | 1.264 (5) | O6—H6B | 0.859 (19) |
C9—N1 | 1.319 (5) | O7—H7A | 0.859 (18) |
C9—C10 | 1.403 (6) | O7—H7B | 0.858 (19) |
O1—Co1—O7 | 87.78 (12) | N1—C9—H9A | 119.0 |
O1—Co1—N2 | 177.61 (12) | C10—C9—H9A | 119.0 |
O7—Co1—N2 | 94.53 (13) | C11—C10—C9 | 119.8 (4) |
O1—Co1—O6 | 85.03 (11) | C11—C10—H10A | 120.1 |
O7—Co1—O6 | 93.97 (12) | C9—C10—H10A | 120.1 |
N2—Co1—O6 | 95.43 (12) | C10—C11—C12 | 120.3 (4) |
O1—Co1—N1 | 100.63 (12) | C10—C11—H11A | 119.9 |
O7—Co1—N1 | 93.88 (12) | C12—C11—H11A | 119.9 |
N2—Co1—N1 | 78.61 (12) | C11—C12—C20 | 116.2 (4) |
O6—Co1—N1 | 170.49 (12) | C11—C12—C13 | 124.7 (4) |
O1—Co1—O5 | 86.69 (11) | C20—C12—C13 | 119.0 (4) |
O7—Co1—O5 | 174.34 (13) | C14—C13—C12 | 121.4 (4) |
N2—Co1—O5 | 90.99 (12) | C14—C13—H13A | 119.3 |
O6—Co1—O5 | 86.76 (11) | C12—C13—H13A | 119.3 |
N1—Co1—O5 | 85.96 (12) | C13—C14—C15 | 120.9 (4) |
O2—C1—O1 | 124.7 (4) | C13—C14—H14A | 119.6 |
O2—C1—C2 | 117.6 (4) | C15—C14—H14A | 119.6 |
O1—C1—C2 | 117.7 (4) | C19—C15—C16 | 117.6 (4) |
C1—C2—C7 | 112.0 (3) | C19—C15—C14 | 119.3 (4) |
C1—C2—C3 | 111.9 (3) | C16—C15—C14 | 123.1 (4) |
C7—C2—C3 | 110.8 (3) | C17—C16—C15 | 119.0 (4) |
C1—C2—H2A | 107.3 | C17—C16—H16A | 120.5 |
C7—C2—H2A | 107.3 | C15—C16—H16A | 120.5 |
C3—C2—H2A | 107.3 | C16—C17—C18 | 119.4 (4) |
C4—C3—C2 | 111.6 (4) | C16—C17—H17A | 120.3 |
C4—C3—H3A | 109.3 | C18—C17—H17A | 120.3 |
C2—C3—H3A | 109.3 | N2—C18—C17 | 123.8 (4) |
C4—C3—H3B | 109.3 | N2—C18—H18A | 118.1 |
C2—C3—H3B | 109.3 | C17—C18—H18A | 118.1 |
H3A—C3—H3B | 108.0 | N2—C19—C15 | 122.9 (4) |
C5—C4—C3 | 123.3 (4) | N2—C19—C20 | 116.8 (3) |
C5—C4—H4A | 118.3 | C15—C19—C20 | 120.3 (4) |
C3—C4—H4A | 118.3 | N1—C20—C12 | 123.0 (4) |
C4—C5—C6 | 124.8 (5) | N1—C20—C19 | 117.9 (3) |
C4—C5—H5C | 117.6 | C12—C20—C19 | 119.1 (4) |
C6—C5—H5C | 117.6 | C9—N1—C20 | 118.6 (3) |
C5—C6—C7 | 112.8 (4) | C9—N1—Co1 | 128.3 (3) |
C5—C6—H6C | 109.0 | C20—N1—Co1 | 113.0 (3) |
C7—C6—H6C | 109.0 | C18—N2—C19 | 117.3 (3) |
C5—C6—H6D | 109.0 | C18—N2—Co1 | 129.1 (3) |
C7—C6—H6D | 109.0 | C19—N2—Co1 | 113.6 (2) |
H6C—C6—H6D | 107.8 | C1—O1—Co1 | 126.8 (2) |
C8—C7—C2 | 110.7 (3) | Co1—O5—H5A | 109 (3) |
C8—C7—C6 | 114.2 (3) | Co1—O5—H5B | 107 (3) |
C2—C7—C6 | 112.3 (3) | H5A—O5—H5B | 108 (3) |
C8—C7—H7C | 106.4 | Co1—O6—H6A | 119 (3) |
C2—C7—H7C | 106.4 | Co1—O6—H6B | 110 (3) |
C6—C7—H7C | 106.4 | H6A—O6—H6B | 107 (3) |
O3—C8—O4 | 123.2 (4) | Co1—O7—H7A | 101 (3) |
O3—C8—C7 | 117.1 (4) | Co1—O7—H7B | 133 (3) |
O4—C8—C7 | 119.7 (4) | H7A—O7—H7B | 108 (3) |
N1—C9—C10 | 122.1 (4) | ||
O2—C1—C2—C7 | −179.6 (3) | N2—C19—C20—N1 | 0.4 (5) |
O1—C1—C2—C7 | −3.0 (5) | C15—C19—C20—N1 | −178.9 (4) |
O2—C1—C2—C3 | 55.3 (5) | N2—C19—C20—C12 | 179.7 (3) |
O1—C1—C2—C3 | −128.1 (4) | C15—C19—C20—C12 | 0.4 (6) |
C1—C2—C3—C4 | 77.6 (5) | C10—C9—N1—C20 | −0.1 (6) |
C7—C2—C3—C4 | −48.1 (5) | C10—C9—N1—Co1 | −177.0 (3) |
C2—C3—C4—C5 | 20.1 (7) | C12—C20—N1—C9 | 0.5 (6) |
C3—C4—C5—C6 | 1.7 (9) | C19—C20—N1—C9 | 179.7 (4) |
C4—C5—C6—C7 | 5.8 (7) | C12—C20—N1—Co1 | 177.9 (3) |
C1—C2—C7—C8 | 59.8 (4) | C19—C20—N1—Co1 | −2.9 (4) |
C3—C2—C7—C8 | −174.5 (3) | O1—Co1—N1—C9 | 2.4 (4) |
C1—C2—C7—C6 | −69.1 (4) | O7—Co1—N1—C9 | −86.0 (4) |
C3—C2—C7—C6 | 56.6 (5) | N2—Co1—N1—C9 | −179.9 (4) |
C5—C6—C7—C8 | −161.8 (4) | O5—Co1—N1—C9 | 88.3 (4) |
C5—C6—C7—C2 | −34.8 (5) | O1—Co1—N1—C20 | −174.6 (3) |
C2—C7—C8—O3 | 34.0 (5) | O7—Co1—N1—C20 | 96.9 (3) |
C6—C7—C8—O3 | 161.9 (4) | N2—Co1—N1—C20 | 3.1 (3) |
C2—C7—C8—O4 | −146.7 (4) | O5—Co1—N1—C20 | −88.7 (3) |
C6—C7—C8—O4 | −18.9 (5) | C17—C18—N2—C19 | −0.1 (6) |
N1—C9—C10—C11 | −0.2 (7) | C17—C18—N2—Co1 | 178.9 (3) |
C9—C10—C11—C12 | 0.1 (7) | C15—C19—N2—C18 | 0.7 (6) |
C10—C11—C12—C20 | 0.3 (7) | C20—C19—N2—C18 | −178.6 (4) |
C10—C11—C12—C13 | −179.0 (5) | C15—C19—N2—Co1 | −178.4 (3) |
C11—C12—C13—C14 | −180.0 (5) | C20—C19—N2—Co1 | 2.3 (4) |
C20—C12—C13—C14 | 0.7 (7) | O7—Co1—N2—C18 | 85.1 (4) |
C12—C13—C14—C15 | −0.8 (7) | O6—Co1—N2—C18 | −9.4 (4) |
C13—C14—C15—C19 | 0.7 (7) | N1—Co1—N2—C18 | 178.1 (4) |
C13—C14—C15—C16 | −178.1 (4) | O5—Co1—N2—C18 | −96.2 (4) |
C19—C15—C16—C17 | 0.4 (6) | O1—Co1—N2—C19 | 69 (3) |
C14—C15—C16—C17 | 179.2 (4) | O7—Co1—N2—C19 | −95.9 (3) |
C15—C16—C17—C18 | 0.2 (7) | O6—Co1—N2—C19 | 169.6 (3) |
C16—C17—C18—N2 | −0.4 (7) | N1—Co1—N2—C19 | −2.9 (3) |
C16—C15—C19—N2 | −0.9 (6) | O5—Co1—N2—C19 | 82.8 (3) |
C14—C15—C19—N2 | −179.8 (4) | O2—C1—O1—Co1 | 34.6 (6) |
C16—C15—C19—C20 | 178.4 (4) | C2—C1—O1—Co1 | −141.7 (3) |
C14—C15—C19—C20 | −0.5 (6) | O7—Co1—O1—C1 | −36.1 (3) |
C11—C12—C20—N1 | −0.6 (6) | O6—Co1—O1—C1 | 58.1 (3) |
C13—C12—C20—N1 | 178.8 (4) | N1—Co1—O1—C1 | −129.6 (3) |
C11—C12—C20—C19 | −179.8 (4) | O5—Co1—O1—C1 | 145.1 (3) |
C13—C12—C20—C19 | −0.4 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O3i | 0.85 (3) | 1.85 (3) | 2.695 (4) | 171 (4) |
O5—H5B···O4 | 0.86 (4) | 2.06 (4) | 2.912 (4) | 172 (4) |
O6—H6A···O4i | 0.86 (3) | 1.86 (4) | 2.716 (4) | 174 (5) |
O6—H6B···O3 | 0.86 (3) | 1.99 (3) | 2.835 (4) | 165 (3) |
O7—H7A···O2 | 0.86 (3) | 1.77 (4) | 2.610 (4) | 165 (4) |
O7—H7B···O4ii | 0.86 (3) | 1.87 (3) | 2.734 (4) | 175 (4) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Co(C8H8O4)(C12H8N2)(H2O)3] |
Mr | 461.33 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 8.1730 (16), 20.210 (4), 12.068 (2) |
β (°) | 91.44 (3) |
V (Å3) | 1992.7 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.91 |
Crystal size (mm) | 0.40 × 0.20 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.801, 0.945 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15996, 3606, 2982 |
Rint | 0.073 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.122, 0.99 |
No. of reflections | 3606 |
No. of parameters | 295 |
No. of restraints | 9 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.34 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O3i | 0.85 (3) | 1.85 (3) | 2.695 (4) | 171 (4) |
O5—H5B···O4 | 0.86 (4) | 2.06 (4) | 2.912 (4) | 172 (4) |
O6—H6A···O4i | 0.86 (3) | 1.86 (4) | 2.716 (4) | 174 (5) |
O6—H6B···O3 | 0.86 (3) | 1.99 (3) | 2.835 (4) | 165 (3) |
O7—H7A···O2 | 0.86 (3) | 1.77 (4) | 2.610 (4) | 165 (4) |
O7—H7B···O4ii | 0.86 (3) | 1.87 (3) | 2.734 (4) | 175 (4) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z. |
Acknowledgements
We gratefully acknowledge the Guangxi Natural Science Foundation of China (2010GXNSFD013017, 2012GXNSFBA053017) and the Natural Science Foundation of Guangxi Normal University.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Recently, carboxylic acid (as well as carboxylate) has been widely applied in engineering studies of inorganic-organic hybrid materials and the construction of metal-organic coordination supramolecular complexes (Huang et al., 2010; Ockwig et al., 2005; Rao et al., 2004). Although the Cambridge Structural Database (Allen, 2002) contains a great number of transition metal derivatives of carboxylic acids, the metal derivatives of cis-4-cyclohexene-1,2-dicarboxylate acid documented are surprisingly rare (Kim et al., 2004; Lee et al., 2006). As part of this ongoing work, the title complex, [Co(C8H8O4)(C12H8N2)(H2O)3], has been prepared and structurally characterized (Fig. 1).
In the title compound, the CoII atom is coordinated by two N atoms from a bidentate 1,10-phenanthroline ligand (phen), one O atom from a monodentate cis-4-cyclohexene-1,2-dicarboxylate ligand, and three O atoms from water molecules in a distorted octahedral geometry. The coordinating Co—N and Co—O bond lengths [Co—N 2.107 (3)–2.122 (3) Å; Co—O 2.071 (3)–2.152 (3) Å] agree well with those observed in analogous complexes (Baruah et al., 2007; Hou et al., 2007; Zhang et al., 2008). The crystal packing (Fig. 2) exhibits intra- and inter-molecular O—H···O hydrogen bonds (Table 1) and π–π stacking interactions [Cg1···Cg2iii distance is 3.784 (3) Å (iii = -x, 1-y, 1-z) between the centroids of the (N1-C9-C10-C11-C12-C20) and (C12-C13-C14-C15-C19-C20) six-membered rings] forming a three-dimensional supramolecular network.