Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027572/gk2071sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027572/gk2071Isup2.hkl |
CCDC reference: 654760
Key indicators
- Single-crystal X-ray study
- T = 295 K
- R factor = 0.049
- wR factor = 0.177
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
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For the only crystal structure of the ketoprofen complex, (ketoprofenato)trimethyltin(IV), see: Tahir et al. (1997).
The title complex was prepared by the addition of cobalt diacetate trihydrate (2.31 g, 10 mmol) to a hot aqueous solution of 2-(3-benzoylphenyl)propanoic acid (3.65 g, 10 mmol); the pH was adjusted to 6 with 0.1M sodium hydroxide. The solution was allowed to evaporate at room temperature. Pink prismatic crystals separated from the filtered solution after several days. CH&N analysis. Calc. for C32H36CoO11: C 58.63, H 5.54%. Found: C 58.54, H 5.64%.
The H atoms were placed in calculated positions [C—H = 0.93 and 0.97 Å and Uiso(H) = 1.2Ueq (C) for aromatic H atoms and methine H atoms, respectively, C—H = 0.96 Å and Uiso(H) = 1.5Ueq (C) for methyl group H atoms] and were included in the refinement in the riding-model approximation. The H atoms of water molecules 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).
Crystal structure of only one metal complex of ketoprofen has been reported up till now. Ketoprofen forms with trimethyltin(IV)] a polymeric compound with the carboxylate group acting in a bidentate bridging mode (Tahir et al., 1997). Here we report crystal structure of the first transition metal complex of ketoprofen.
As illustrated in Fig. 1, the crystal structure of the title compound consists of two independent neutral mononuclear CoII complex molecules and one water of crystallization. The CoII atoms of the two molecules lie on inversion centers and display an octahedral geometry defined by two carboxylate O atoms of two ketoprofenato ligands and four water molecules. The Co1—Oketoprofenato and Co2—Oketoprofenato bond lengths are 2.134 (2) and 2.064 (2) Å, respectively. The Co—Owater bond lengths range from 2.051 (3) to 2.183 (2) Å. In the ketoprofenato ligands, two benzene rings are not coplanar, the dihedral angles are 70.1 (3) and 121.7 (3) °. A three-dimensional supramolecular network structure is formed through the extended hydrogen bonding interactions between water molecules and carboxylate O atoms (Table 2).
For the only crystal structure of the ketoprofen complex, (ketoprofenato)trimethyltin(IV), see: Tahir et al. (1997).
Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; 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.
Fig. 1. Molecular structure of of the title compound with 30% probability ellipsoids for the non-H atoms. |
[Co(C16H13O3)2(H2O)4]·H2O | Z = 2 |
Mr = 655.54 | F(000) = 686 |
Triclinic, P1 | Dx = 1.403 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5966 (17) Å | Cell parameters from 9690 reflections |
b = 8.8939 (18) Å | θ = 3.2–27.5° |
c = 21.872 (4) Å | µ = 0.61 mm−1 |
α = 92.08 (3)° | T = 295 K |
β = 99.69 (3)° | Prism, pink |
γ = 108.92 (3)° | 0.36 × 0.28 × 0.19 mm |
V = 1551.9 (6) Å3 |
Rigaku R-AXIS RAPID diffractometer | 7032 independent reflections |
Radiation source: fine-focus sealed tube | 4192 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
Detector resolution: 10.000 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −11→11 |
Tmin = 0.810, Tmax = 0.892 | l = −28→28 |
15351 measured reflections |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.177 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0981P)2] where P = (Fo2 + 2Fc2)/3 |
7032 reflections | (Δ/σ)max < 0.001 |
432 parameters | Δρmax = 0.75 e Å−3 |
15 restraints | Δρmin = −0.62 e Å−3 |
[Co(C16H13O3)2(H2O)4]·H2O | γ = 108.92 (3)° |
Mr = 655.54 | V = 1551.9 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.5966 (17) Å | Mo Kα radiation |
b = 8.8939 (18) Å | µ = 0.61 mm−1 |
c = 21.872 (4) Å | T = 295 K |
α = 92.08 (3)° | 0.36 × 0.28 × 0.19 mm |
β = 99.69 (3)° |
Rigaku R-AXIS RAPID diffractometer | 7032 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 4192 reflections with I > 2σ(I) |
Tmin = 0.810, Tmax = 0.892 | Rint = 0.049 |
15351 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 15 restraints |
wR(F2) = 0.177 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.75 e Å−3 |
7032 reflections | Δρmin = −0.62 e Å−3 |
432 parameters |
x | y | z | Uiso*/Ueq | ||
Co1 | 0.5000 | 0.0000 | 0.5000 | 0.02863 (19) | |
Co2 | 0.0000 | 0.5000 | 0.5000 | 0.02836 (19) | |
O1 | 0.7225 (4) | −0.1111 (3) | 0.61833 (13) | 0.0555 (8) | |
O1W | −0.1286 (5) | 0.6695 (4) | 0.63546 (13) | 0.0560 (8) | |
O2 | 0.7012 (3) | 0.1050 (3) | 0.57693 (10) | 0.0336 (5) | |
O2W | 0.3229 (3) | 0.0047 (3) | 0.55380 (13) | 0.0405 (6) | |
O3W | 0.4817 (3) | −0.2333 (3) | 0.51952 (12) | 0.0401 (6) | |
O3 | 0.2059 (3) | 0.2647 (3) | 0.56416 (12) | 0.0432 (6) | |
O4 | 0.2168 (3) | 0.5170 (3) | 0.56140 (12) | 0.0417 (6) | |
O4W | −0.1442 (4) | 0.4111 (3) | 0.56481 (13) | 0.0457 (7) | |
O5W | 0.0284 (3) | 0.7437 (3) | 0.53313 (12) | 0.0364 (6) | |
O5 | 0.9239 (5) | 0.6840 (4) | 0.76371 (14) | 0.0666 (10) | |
O6 | 0.3928 (5) | 0.6321 (4) | 0.91110 (14) | 0.0765 (11) | |
C1 | 0.9958 (9) | 0.6929 (7) | 0.9782 (2) | 0.0874 (19) | |
H1 | 1.0615 | 0.6735 | 1.0133 | 0.105* | |
C2 | 0.9025 (9) | 0.7898 (7) | 0.9845 (3) | 0.090 (2) | |
H2 | 0.9021 | 0.8328 | 1.0238 | 0.108* | |
C3 | 0.8116 (9) | 0.8226 (7) | 0.9336 (3) | 0.0860 (19) | |
H3 | 0.7489 | 0.8886 | 0.9381 | 0.103* | |
C4 | 0.8102 (7) | 0.7592 (5) | 0.8744 (2) | 0.0638 (13) | |
H4 | 0.7498 | 0.7853 | 0.8395 | 0.077* | |
C5 | 0.8998 (6) | 0.6566 (5) | 0.86799 (19) | 0.0469 (10) | |
C6 | 0.9929 (7) | 0.6236 (6) | 0.9199 (2) | 0.0662 (14) | |
H6 | 1.0536 | 0.5553 | 0.9160 | 0.079* | |
C7 | 0.8989 (5) | 0.5920 (5) | 0.80391 (18) | 0.0436 (9) | |
C8 | 0.8629 (5) | 0.4175 (5) | 0.78967 (17) | 0.0412 (9) | |
C9 | 0.9120 (5) | 0.3631 (4) | 0.73750 (15) | 0.0351 (8) | |
H9 | 0.9773 | 0.4365 | 0.7149 | 0.042* | |
C10 | 0.8645 (5) | 0.2020 (4) | 0.71943 (16) | 0.0359 (8) | |
C11 | 0.7664 (6) | 0.0951 (5) | 0.75340 (19) | 0.0531 (11) | |
H11 | 0.7331 | −0.0139 | 0.7415 | 0.064* | |
C12 | 0.7169 (7) | 0.1480 (5) | 0.8050 (2) | 0.0655 (14) | |
H12 | 0.6495 | 0.0747 | 0.8271 | 0.079* | |
C13 | 0.7674 (6) | 0.3083 (5) | 0.82348 (19) | 0.0523 (11) | |
H13 | 0.7372 | 0.3434 | 0.8588 | 0.063* | |
C14 | 0.9233 (5) | 0.1427 (4) | 0.66370 (15) | 0.0343 (8) | |
H14 | 0.9803 | 0.2361 | 0.6435 | 0.041* | |
C15 | 1.0479 (5) | 0.0574 (5) | 0.68472 (18) | 0.0449 (10) | |
H15A | 1.1453 | 0.1305 | 0.7115 | 0.067* | |
H15B | 1.0799 | 0.0187 | 0.6489 | 0.067* | |
H15C | 0.9969 | −0.0309 | 0.7070 | 0.067* | |
C16 | 0.7703 (5) | 0.0361 (4) | 0.61625 (16) | 0.0338 (8) | |
C17 | 0.2352 (7) | 0.0842 (6) | 0.8625 (2) | 0.0667 (14) | |
H17 | 0.1514 | −0.0046 | 0.8402 | 0.080* | |
C18 | 0.3483 (8) | 0.0650 (7) | 0.9110 (2) | 0.0745 (16) | |
H18 | 0.3432 | −0.0370 | 0.9209 | 0.089* | |
C19 | 0.4708 (7) | 0.1977 (6) | 0.9453 (2) | 0.0659 (14) | |
H19 | 0.5472 | 0.1844 | 0.9784 | 0.079* | |
C20 | 0.4789 (6) | 0.3479 (6) | 0.93060 (18) | 0.0573 (12) | |
H20 | 0.5594 | 0.4365 | 0.9543 | 0.069* | |
C21 | 0.3676 (5) | 0.3689 (5) | 0.88030 (17) | 0.0469 (10) | |
C22 | 0.2456 (6) | 0.2351 (5) | 0.84673 (19) | 0.0543 (11) | |
H22 | 0.1699 | 0.2475 | 0.8132 | 0.065* | |
C23 | 0.3743 (6) | 0.5346 (5) | 0.86745 (19) | 0.0522 (11) | |
C24 | 0.3617 (5) | 0.5821 (4) | 0.80224 (18) | 0.0420 (9) | |
C25 | 0.3313 (6) | 0.7258 (5) | 0.7927 (2) | 0.0541 (11) | |
H25 | 0.3137 | 0.7842 | 0.8254 | 0.065* | |
C26 | 0.3277 (6) | 0.7794 (5) | 0.7345 (2) | 0.0608 (13) | |
H26 | 0.3070 | 0.8745 | 0.7282 | 0.073* | |
C27 | 0.3540 (6) | 0.6956 (5) | 0.6852 (2) | 0.0524 (11) | |
H27 | 0.3514 | 0.7349 | 0.6464 | 0.063* | |
C28 | 0.3846 (5) | 0.5518 (5) | 0.69338 (17) | 0.0412 (9) | |
C29 | 0.3868 (5) | 0.4972 (5) | 0.75199 (17) | 0.0414 (9) | |
H29 | 0.4056 | 0.4011 | 0.7580 | 0.050* | |
C30 | 0.4215 (5) | 0.4663 (5) | 0.63817 (17) | 0.0444 (10) | |
H30 | 0.5069 | 0.5487 | 0.6219 | 0.053* | |
C31 | 0.4963 (6) | 0.3409 (6) | 0.6545 (2) | 0.0581 (12) | |
H31A | 0.5943 | 0.3850 | 0.6866 | 0.087* | |
H31B | 0.5268 | 0.3025 | 0.6183 | 0.087* | |
H31C | 0.4163 | 0.2542 | 0.6693 | 0.087* | |
C32 | 0.2669 (5) | 0.4081 (4) | 0.58425 (16) | 0.0351 (8) | |
H3W1 | 0.554 (4) | −0.213 (4) | 0.5531 (11) | 0.053* | |
H1W1 | −0.185 (5) | 0.732 (4) | 0.6325 (16) | 0.053* | |
H2W1 | 0.296 (4) | 0.088 (2) | 0.551 (2) | 0.053* | |
H2W2 | 0.234 (3) | −0.076 (3) | 0.5474 (19) | 0.053* | |
H3W2 | 0.395 (3) | −0.311 (3) | 0.5224 (16) | 0.053* | |
H4W1 | −0.202 (5) | 0.3180 (18) | 0.5707 (18) | 0.053* | |
H5W1 | −0.049 (4) | 0.750 (5) | 0.5046 (12) | 0.053* | |
H1W2 | −0.082 (5) | 0.672 (5) | 0.6731 (8) | 0.053* | |
H4W2 | −0.166 (5) | 0.481 (3) | 0.5861 (17) | 0.053* | |
H5W2 | −0.009 (4) | 0.721 (5) | 0.5663 (10) | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0258 (4) | 0.0237 (3) | 0.0323 (3) | 0.0044 (3) | 0.0025 (3) | 0.0026 (3) |
Co2 | 0.0252 (4) | 0.0243 (3) | 0.0320 (3) | 0.0048 (3) | 0.0028 (3) | 0.0030 (3) |
O1 | 0.0560 (19) | 0.0321 (14) | 0.0627 (18) | 0.0085 (13) | −0.0203 (15) | 0.0110 (13) |
O1W | 0.084 (3) | 0.0487 (17) | 0.0439 (16) | 0.0372 (17) | 0.0068 (15) | −0.0004 (14) |
O2 | 0.0301 (14) | 0.0295 (12) | 0.0366 (12) | 0.0082 (10) | −0.0028 (10) | 0.0041 (10) |
O2W | 0.0346 (15) | 0.0307 (13) | 0.0545 (15) | 0.0071 (11) | 0.0122 (12) | −0.0009 (12) |
O3W | 0.0333 (15) | 0.0288 (12) | 0.0478 (15) | 0.0002 (11) | −0.0007 (11) | 0.0091 (11) |
O3 | 0.0428 (16) | 0.0380 (14) | 0.0473 (15) | 0.0152 (12) | 0.0007 (12) | 0.0059 (12) |
O4 | 0.0341 (15) | 0.0326 (13) | 0.0513 (15) | 0.0106 (11) | −0.0101 (12) | 0.0044 (11) |
O4W | 0.0594 (19) | 0.0279 (13) | 0.0486 (16) | 0.0049 (13) | 0.0264 (13) | 0.0047 (12) |
O5W | 0.0349 (15) | 0.0288 (12) | 0.0419 (14) | 0.0063 (11) | 0.0069 (11) | 0.0012 (11) |
O5 | 0.113 (3) | 0.0494 (17) | 0.0480 (17) | 0.0370 (19) | 0.0229 (18) | 0.0081 (15) |
O6 | 0.116 (3) | 0.072 (2) | 0.0417 (17) | 0.037 (2) | 0.0081 (18) | −0.0142 (16) |
C1 | 0.122 (6) | 0.082 (4) | 0.044 (3) | 0.019 (4) | 0.004 (3) | 0.002 (3) |
C2 | 0.136 (6) | 0.061 (3) | 0.059 (3) | 0.005 (4) | 0.040 (4) | −0.017 (3) |
C3 | 0.104 (5) | 0.070 (3) | 0.089 (4) | 0.024 (3) | 0.047 (4) | −0.016 (3) |
C4 | 0.073 (4) | 0.054 (3) | 0.067 (3) | 0.024 (3) | 0.017 (2) | −0.006 (2) |
C5 | 0.055 (3) | 0.036 (2) | 0.047 (2) | 0.0096 (19) | 0.0177 (19) | −0.0023 (18) |
C6 | 0.085 (4) | 0.069 (3) | 0.047 (3) | 0.028 (3) | 0.011 (2) | 0.004 (2) |
C7 | 0.050 (3) | 0.043 (2) | 0.039 (2) | 0.0201 (19) | 0.0069 (17) | −0.0001 (18) |
C8 | 0.039 (2) | 0.043 (2) | 0.0383 (19) | 0.0115 (18) | 0.0054 (16) | 0.0009 (17) |
C9 | 0.037 (2) | 0.0393 (19) | 0.0296 (17) | 0.0146 (16) | 0.0031 (14) | 0.0029 (15) |
C10 | 0.034 (2) | 0.0374 (19) | 0.0323 (18) | 0.0091 (16) | 0.0015 (15) | 0.0004 (15) |
C11 | 0.061 (3) | 0.039 (2) | 0.052 (2) | 0.004 (2) | 0.016 (2) | −0.0024 (19) |
C12 | 0.082 (4) | 0.049 (3) | 0.057 (3) | 0.002 (2) | 0.033 (3) | 0.003 (2) |
C13 | 0.065 (3) | 0.051 (2) | 0.043 (2) | 0.017 (2) | 0.021 (2) | 0.0014 (19) |
C14 | 0.033 (2) | 0.0337 (18) | 0.0319 (17) | 0.0084 (15) | 0.0009 (14) | 0.0011 (15) |
C15 | 0.038 (2) | 0.046 (2) | 0.047 (2) | 0.0157 (18) | −0.0043 (17) | −0.0044 (18) |
C16 | 0.034 (2) | 0.0297 (17) | 0.0347 (18) | 0.0071 (15) | 0.0052 (15) | 0.0020 (15) |
C17 | 0.087 (4) | 0.057 (3) | 0.050 (3) | 0.016 (3) | 0.012 (2) | 0.000 (2) |
C18 | 0.122 (5) | 0.067 (3) | 0.048 (3) | 0.046 (3) | 0.027 (3) | 0.013 (2) |
C19 | 0.085 (4) | 0.083 (4) | 0.039 (2) | 0.042 (3) | 0.006 (2) | 0.005 (2) |
C20 | 0.062 (3) | 0.073 (3) | 0.034 (2) | 0.023 (3) | 0.0009 (19) | −0.005 (2) |
C21 | 0.050 (3) | 0.054 (2) | 0.0337 (19) | 0.017 (2) | 0.0049 (17) | −0.0023 (18) |
C22 | 0.059 (3) | 0.059 (3) | 0.039 (2) | 0.018 (2) | −0.0022 (19) | −0.002 (2) |
C23 | 0.052 (3) | 0.057 (3) | 0.041 (2) | 0.015 (2) | 0.0042 (18) | −0.010 (2) |
C24 | 0.040 (2) | 0.041 (2) | 0.041 (2) | 0.0141 (18) | 0.0005 (16) | −0.0052 (17) |
C25 | 0.061 (3) | 0.054 (3) | 0.050 (2) | 0.027 (2) | 0.003 (2) | −0.008 (2) |
C26 | 0.077 (4) | 0.049 (2) | 0.060 (3) | 0.033 (2) | 0.002 (2) | −0.008 (2) |
C27 | 0.063 (3) | 0.049 (2) | 0.046 (2) | 0.025 (2) | 0.002 (2) | 0.0027 (19) |
C28 | 0.043 (2) | 0.045 (2) | 0.0362 (19) | 0.0198 (18) | −0.0018 (16) | −0.0020 (17) |
C29 | 0.041 (2) | 0.042 (2) | 0.041 (2) | 0.0170 (18) | 0.0008 (16) | −0.0052 (17) |
C30 | 0.048 (3) | 0.050 (2) | 0.0351 (19) | 0.021 (2) | 0.0001 (17) | 0.0011 (17) |
C31 | 0.048 (3) | 0.075 (3) | 0.054 (3) | 0.030 (2) | −0.002 (2) | −0.006 (2) |
C32 | 0.031 (2) | 0.041 (2) | 0.0337 (18) | 0.0121 (16) | 0.0086 (15) | 0.0025 (16) |
Co1—O2W | 2.084 (3) | C9—H9 | 0.9300 |
Co1—O3W | 2.095 (2) | C10—C11 | 1.382 (6) |
Co1—O2 | 2.134 (2) | C10—C14 | 1.534 (5) |
Co2—O4W | 2.051 (3) | C11—C12 | 1.389 (6) |
Co2—O4 | 2.064 (2) | C11—H11 | 0.9300 |
Co2—O5W | 2.183 (2) | C12—C13 | 1.372 (6) |
Co1—O2Wi | 2.084 (3) | C12—H12 | 0.9300 |
Co1—O3Wi | 2.095 (2) | C13—H13 | 0.9300 |
Co1—O2i | 2.134 (2) | C14—C15 | 1.524 (5) |
Co2—O4Wii | 2.051 (3) | C14—C16 | 1.539 (5) |
Co2—O4ii | 2.064 (2) | C14—H14 | 0.9800 |
Co2—O5Wii | 2.183 (2) | C15—H15A | 0.9600 |
O1—C16 | 1.244 (4) | C15—H15B | 0.9600 |
O1W—H1W1 | 0.85 (4) | C15—H15C | 0.9600 |
O1W—H1W2 | 0.848 (10) | C17—C18 | 1.369 (7) |
O2—C16 | 1.253 (4) | C17—C22 | 1.376 (7) |
O2W—H2W1 | 0.850 (10) | C17—H17 | 0.9300 |
O2W—H2W2 | 0.85 (3) | C18—C19 | 1.389 (8) |
O3W—H3W1 | 0.85 (3) | C18—H18 | 0.9300 |
O3W—H3W2 | 0.85 (3) | C19—C20 | 1.368 (7) |
O3—C32 | 1.242 (4) | C19—H19 | 0.9300 |
O4—C32 | 1.268 (4) | C20—C21 | 1.392 (6) |
O4W—H4W1 | 0.845 (10) | C20—H20 | 0.9300 |
O4W—H4W2 | 0.85 (4) | C21—C22 | 1.387 (6) |
O5W—H5W1 | 0.85 (3) | C21—C23 | 1.495 (6) |
O5W—H5W2 | 0.85 (3) | C22—H22 | 0.9300 |
O5—C7 | 1.221 (5) | C23—C24 | 1.499 (6) |
O6—C23 | 1.220 (5) | C24—C29 | 1.396 (5) |
C1—C2 | 1.370 (9) | C24—C25 | 1.401 (6) |
C1—C6 | 1.390 (7) | C25—C26 | 1.375 (6) |
C1—H1 | 0.9300 | C25—H25 | 0.9300 |
C2—C3 | 1.347 (9) | C26—C27 | 1.379 (6) |
C2—H2 | 0.9300 | C26—H26 | 0.9300 |
C3—C4 | 1.389 (7) | C27—C28 | 1.399 (6) |
C3—H3 | 0.9300 | C27—H27 | 0.9300 |
C4—C5 | 1.389 (6) | C28—C29 | 1.386 (5) |
C4—H4 | 0.9300 | C28—C30 | 1.535 (5) |
C5—C6 | 1.373 (6) | C29—H29 | 0.9300 |
C5—C7 | 1.494 (5) | C30—C31 | 1.484 (6) |
C6—H6 | 0.9300 | C30—C32 | 1.551 (5) |
C7—C8 | 1.490 (5) | C30—H30 | 0.9800 |
C8—C13 | 1.380 (6) | C31—H31A | 0.9600 |
C8—C9 | 1.403 (5) | C31—H31B | 0.9600 |
C9—C10 | 1.379 (5) | C31—H31C | 0.9600 |
O2W—Co1—O3W | 91.81 (11) | C12—C11—H11 | 119.5 |
O2W—Co1—O3Wi | 88.19 (11) | C13—C12—C11 | 120.0 (4) |
O2W—Co1—O2i | 88.33 (10) | C13—C12—H12 | 120.0 |
O3W—Co1—O2i | 86.82 (10) | C11—C12—H12 | 120.0 |
O2W—Co1—O2 | 91.67 (10) | C12—C13—C8 | 120.1 (4) |
O3W—Co1—O2 | 93.18 (10) | C12—C13—H13 | 120.0 |
O4W—Co2—O4ii | 88.35 (12) | C8—C13—H13 | 120.0 |
O4W—Co2—O5Wii | 89.34 (10) | C15—C14—C10 | 111.2 (3) |
O4—Co2—O5Wii | 90.54 (10) | C15—C14—C16 | 112.2 (3) |
O4W—Co2—O5W | 90.66 (10) | C10—C14—C16 | 109.5 (3) |
O4—Co2—O5W | 89.46 (10) | C15—C14—H14 | 108.0 |
O2Wi—Co1—O2W | 180.000 (1) | C10—C14—H14 | 108.0 |
O2Wi—Co1—O3W | 88.19 (11) | C16—C14—H14 | 108.0 |
O2Wi—Co1—O3Wi | 91.81 (11) | C14—C15—H15A | 109.5 |
O3W—Co1—O3Wi | 180.00 (3) | C14—C15—H15B | 109.5 |
O2Wi—Co1—O2i | 91.67 (10) | H15A—C15—H15B | 109.5 |
O3Wi—Co1—O2i | 93.18 (10) | C14—C15—H15C | 109.5 |
O2Wi—Co1—O2 | 88.33 (10) | H15A—C15—H15C | 109.5 |
O3Wi—Co1—O2 | 86.82 (10) | H15B—C15—H15C | 109.5 |
O2i—Co1—O2 | 180.0 | O1—C16—O2 | 123.7 (3) |
O4W—Co2—O4Wii | 180.000 (1) | O1—C16—C14 | 119.4 (3) |
O4Wii—Co2—O4ii | 91.65 (12) | O2—C16—C14 | 116.9 (3) |
O4W—Co2—O4 | 91.65 (12) | C18—C17—C22 | 119.9 (5) |
O4Wii—Co2—O4 | 88.35 (12) | C18—C17—H17 | 120.1 |
O4ii—Co2—O4 | 180.000 (1) | C22—C17—H17 | 120.1 |
O4Wii—Co2—O5Wii | 90.66 (10) | C17—C18—C19 | 120.1 (5) |
O4ii—Co2—O5Wii | 89.46 (10) | C17—C18—H18 | 119.9 |
O4Wii—Co2—O5W | 89.34 (10) | C19—C18—H18 | 119.9 |
O4ii—Co2—O5W | 90.54 (10) | C20—C19—C18 | 120.0 (5) |
O5Wii—Co2—O5W | 180.00 (13) | C20—C19—H19 | 120.0 |
H1W1—O1W—H1W2 | 110 (2) | C18—C19—H19 | 120.0 |
C16—O2—Co1 | 128.2 (2) | C19—C20—C21 | 120.4 (4) |
Co1—O2W—H2W1 | 113 (3) | C19—C20—H20 | 119.8 |
Co1—O2W—H2W2 | 116 (3) | C21—C20—H20 | 119.8 |
H2W1—O2W—H2W2 | 108 (2) | C22—C21—C20 | 118.8 (4) |
Co1—O3W—H3W1 | 99 (3) | C22—C21—C23 | 122.0 (4) |
Co1—O3W—H3W2 | 129 (3) | C20—C21—C23 | 119.0 (4) |
H3W1—O3W—H3W2 | 111 (2) | C17—C22—C21 | 120.7 (4) |
C32—O4—Co2 | 130.0 (2) | C17—C22—H22 | 119.6 |
Co2—O4W—H4W1 | 133 (2) | C21—C22—H22 | 119.6 |
Co2—O4W—H4W2 | 115 (2) | O6—C23—C21 | 118.9 (4) |
H4W1—O4W—H4W2 | 111 (2) | O6—C23—C24 | 120.1 (4) |
Co2—O5W—H5W1 | 94 (3) | C21—C23—C24 | 120.9 (3) |
Co2—O5W—H5W2 | 96 (3) | C29—C24—C25 | 118.8 (4) |
H5W1—O5W—H5W2 | 110 (2) | C29—C24—C23 | 124.3 (4) |
C2—C1—C6 | 120.6 (6) | C25—C24—C23 | 116.8 (4) |
C2—C1—H1 | 119.7 | C26—C25—C24 | 119.2 (4) |
C6—C1—H1 | 119.7 | C26—C25—H25 | 120.4 |
C3—C2—C1 | 119.9 (5) | C24—C25—H25 | 120.4 |
C3—C2—H2 | 120.0 | C25—C26—C27 | 121.7 (4) |
C1—C2—H2 | 120.0 | C25—C26—H26 | 119.1 |
C2—C3—C4 | 121.0 (6) | C27—C26—H26 | 119.1 |
C2—C3—H3 | 119.5 | C26—C27—C28 | 120.3 (4) |
C4—C3—H3 | 119.5 | C26—C27—H27 | 119.9 |
C5—C4—C3 | 119.3 (5) | C28—C27—H27 | 119.9 |
C5—C4—H4 | 120.3 | C29—C28—C27 | 118.0 (4) |
C3—C4—H4 | 120.3 | C29—C28—C30 | 123.3 (3) |
C6—C5—C4 | 119.7 (4) | C27—C28—C30 | 118.7 (4) |
C6—C5—C7 | 121.8 (4) | C28—C29—C24 | 122.0 (4) |
C4—C5—C7 | 118.5 (4) | C28—C29—H29 | 119.0 |
C5—C6—C1 | 119.5 (5) | C24—C29—H29 | 119.0 |
C5—C6—H6 | 120.3 | C31—C30—C28 | 115.1 (3) |
C1—C6—H6 | 120.3 | C31—C30—C32 | 113.2 (3) |
O5—C7—C8 | 121.4 (3) | C28—C30—C32 | 111.2 (3) |
O5—C7—C5 | 118.6 (3) | C31—C30—H30 | 105.5 |
C8—C7—C5 | 120.0 (4) | C28—C30—H30 | 105.5 |
C13—C8—C9 | 119.5 (4) | C32—C30—H30 | 105.5 |
C13—C8—C7 | 120.6 (4) | C30—C31—H31A | 109.5 |
C9—C8—C7 | 119.6 (4) | C30—C31—H31B | 109.5 |
C10—C9—C8 | 120.7 (4) | H31A—C31—H31B | 109.5 |
C10—C9—H9 | 119.7 | C30—C31—H31C | 109.5 |
C8—C9—H9 | 119.7 | H31A—C31—H31C | 109.5 |
C9—C10—C11 | 118.7 (3) | H31B—C31—H31C | 109.5 |
C9—C10—C14 | 120.5 (3) | O3—C32—O4 | 124.3 (3) |
C11—C10—C14 | 120.7 (3) | O3—C32—C30 | 120.3 (3) |
C10—C11—C12 | 120.9 (4) | O4—C32—C30 | 115.3 (3) |
C10—C11—H11 | 119.5 | ||
O2Wi—Co1—O2—C16 | −88.5 (3) | C15—C14—C16—O1 | 29.8 (5) |
O2W—Co1—O2—C16 | 91.5 (3) | C10—C14—C16—O1 | −94.1 (4) |
O3W—Co1—O2—C16 | −0.4 (3) | C15—C14—C16—O2 | −149.8 (3) |
O3Wi—Co1—O2—C16 | 179.6 (3) | C10—C14—C16—O2 | 86.3 (4) |
O4W—Co2—O4—C32 | 67.1 (3) | C22—C17—C18—C19 | 1.7 (8) |
O4Wii—Co2—O4—C32 | −112.9 (3) | C17—C18—C19—C20 | −0.3 (8) |
O5Wii—Co2—O4—C32 | −22.2 (3) | C18—C19—C20—C21 | −1.6 (8) |
O5W—Co2—O4—C32 | 157.8 (3) | C19—C20—C21—C22 | 1.9 (7) |
C6—C1—C2—C3 | −2.2 (10) | C19—C20—C21—C23 | 176.9 (4) |
C1—C2—C3—C4 | 0.2 (10) | C18—C17—C22—C21 | −1.3 (8) |
C2—C3—C4—C5 | 2.0 (9) | C20—C21—C22—C17 | −0.4 (7) |
C3—C4—C5—C6 | −2.2 (8) | C23—C21—C22—C17 | −175.3 (5) |
C3—C4—C5—C7 | −179.0 (5) | C22—C21—C23—O6 | 133.1 (5) |
C4—C5—C6—C1 | 0.2 (8) | C20—C21—C23—O6 | −41.8 (7) |
C7—C5—C6—C1 | 176.9 (5) | C22—C21—C23—C24 | −48.1 (6) |
C2—C1—C6—C5 | 2.0 (9) | C20—C21—C23—C24 | 137.1 (4) |
C6—C5—C7—O5 | −129.8 (5) | O6—C23—C24—C29 | 161.5 (4) |
C4—C5—C7—O5 | 46.9 (6) | C21—C23—C24—C29 | −17.4 (7) |
C6—C5—C7—C8 | 52.0 (6) | O6—C23—C24—C25 | −15.1 (7) |
C4—C5—C7—C8 | −131.3 (4) | C21—C23—C24—C25 | 166.1 (4) |
O5—C7—C8—C13 | −151.7 (4) | C29—C24—C25—C26 | −0.3 (7) |
C5—C7—C8—C13 | 26.4 (6) | C23—C24—C25—C26 | 176.5 (4) |
O5—C7—C8—C9 | 21.7 (6) | C24—C25—C26—C27 | −0.3 (8) |
C5—C7—C8—C9 | −160.1 (4) | C25—C26—C27—C28 | 0.3 (8) |
C13—C8—C9—C10 | 0.6 (6) | C26—C27—C28—C29 | 0.2 (7) |
C7—C8—C9—C10 | −172.9 (3) | C26—C27—C28—C30 | −177.1 (4) |
C8—C9—C10—C11 | 0.5 (6) | C27—C28—C29—C24 | −0.8 (6) |
C8—C9—C10—C14 | −177.9 (3) | C30—C28—C29—C24 | 176.4 (4) |
C9—C10—C11—C12 | −0.3 (7) | C25—C24—C29—C28 | 0.8 (6) |
C14—C10—C11—C12 | 178.1 (4) | C23—C24—C29—C28 | −175.7 (4) |
C10—C11—C12—C13 | −0.9 (8) | C29—C28—C30—C31 | −12.9 (6) |
C11—C12—C13—C8 | 2.1 (8) | C27—C28—C30—C31 | 164.3 (4) |
C9—C8—C13—C12 | −1.9 (7) | C29—C28—C30—C32 | 117.4 (4) |
C7—C8—C13—C12 | 171.6 (4) | C27—C28—C30—C32 | −65.4 (5) |
C9—C10—C14—C15 | 110.7 (4) | Co2—O4—C32—O3 | 14.4 (6) |
C11—C10—C14—C15 | −67.7 (5) | Co2—O4—C32—C30 | −169.4 (2) |
C9—C10—C14—C16 | −124.8 (4) | C31—C30—C32—O3 | 8.2 (5) |
C11—C10—C14—C16 | 56.8 (5) | C28—C30—C32—O3 | −123.1 (4) |
Co1—O2—C16—O1 | −4.6 (6) | C31—C30—C32—O4 | −168.2 (4) |
Co1—O2—C16—C14 | 174.9 (2) | C28—C30—C32—O4 | 60.5 (5) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3W—H3W1···O1 | 0.85 (3) | 1.82 (3) | 2.646 (4) | 164 (4) |
O1W—H1W1···O1iii | 0.85 (4) | 1.83 (4) | 2.665 (4) | 170 (4) |
O2W—H2W1···O3 | 0.85 (1) | 1.99 (2) | 2.822 (4) | 166 (4) |
O2W—H2W2···O5Wiv | 0.85 (3) | 1.93 (3) | 2.781 (4) | 179 (4) |
O3W—H3W2···O4iv | 0.85 (3) | 2.11 (2) | 2.920 (4) | 161 (3) |
O4W—H4W1···O2v | 0.85 (3) | 1.83 (1) | 2.660 (4) | 169 (4) |
O5W—H5W1···O3ii | 0.85 (3) | 1.81 (3) | 2.653 (4) | 170 (4) |
O1W—H1W2···O5v | 0.85 (1) | 1.97 (2) | 2.757 (4) | 154 (4) |
O4W—H4W2···O1W | 0.85 (4) | 1.87 (2) | 2.675 (4) | 159 (4) |
O5W—H5W2···O1W | 0.85 (3) | 1.96 (3) | 2.795 (4) | 171 (4) |
Symmetry codes: (ii) −x, −y+1, −z+1; (iii) x−1, y+1, z; (iv) x, y−1, z; (v) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Co(C16H13O3)2(H2O)4]·H2O |
Mr | 655.54 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 8.5966 (17), 8.8939 (18), 21.872 (4) |
α, β, γ (°) | 92.08 (3), 99.69 (3), 108.92 (3) |
V (Å3) | 1551.9 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.61 |
Crystal size (mm) | 0.36 × 0.28 × 0.19 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.810, 0.892 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15351, 7032, 4192 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.177, 1.05 |
No. of reflections | 7032 |
No. of parameters | 432 |
No. of restraints | 15 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.75, −0.62 |
Computer programs: RAPID-AUTO (Rigaku Corporation, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.
Co1—O2W | 2.084 (3) | Co2—O4W | 2.051 (3) |
Co1—O3W | 2.095 (2) | Co2—O4 | 2.064 (2) |
Co1—O2 | 2.134 (2) | Co2—O5W | 2.183 (2) |
O2W—Co1—O3W | 91.81 (11) | O4W—Co2—O4ii | 88.35 (12) |
O2W—Co1—O3Wi | 88.19 (11) | O4W—Co2—O5Wii | 89.34 (10) |
O2W—Co1—O2i | 88.33 (10) | O4—Co2—O5Wii | 90.54 (10) |
O3W—Co1—O2i | 86.82 (10) | O4W—Co2—O5W | 90.66 (10) |
O2W—Co1—O2 | 91.67 (10) | O4—Co2—O5W | 89.46 (10) |
O3W—Co1—O2 | 93.18 (10) | O4W—Co2—O4 | 91.65 (12) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3W—H3W1···O1 | 0.85 (3) | 1.82 (3) | 2.646 (4) | 164 (4) |
O1W—H1W1···O1iii | 0.85 (4) | 1.83 (4) | 2.665 (4) | 170 (4) |
O2W—H2W1···O3 | 0.850 (10) | 1.990 (15) | 2.822 (4) | 166 (4) |
O2W—H2W2···O5Wiv | 0.85 (3) | 1.93 (3) | 2.781 (4) | 179 (4) |
O3W—H3W2···O4iv | 0.85 (3) | 2.107 (16) | 2.920 (4) | 161 (3) |
O4W—H4W1···O2v | 0.85 (3) | 1.826 (12) | 2.660 (4) | 169 (4) |
O5W—H5W1···O3ii | 0.85 (3) | 1.81 (3) | 2.653 (4) | 170 (4) |
O1W—H1W2···O5v | 0.848 (10) | 1.97 (2) | 2.757 (4) | 154 (4) |
O4W—H4W2···O1W | 0.85 (4) | 1.867 (16) | 2.675 (4) | 159 (4) |
O5W—H5W2···O1W | 0.85 (3) | 1.96 (3) | 2.795 (4) | 171 (4) |
Symmetry codes: (ii) −x, −y+1, −z+1; (iii) x−1, y+1, z; (iv) x, y−1, z; (v) x−1, y, z. |
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Crystal structure of only one metal complex of ketoprofen has been reported up till now. Ketoprofen forms with trimethyltin(IV)] a polymeric compound with the carboxylate group acting in a bidentate bridging mode (Tahir et al., 1997). Here we report crystal structure of the first transition metal complex of ketoprofen.
As illustrated in Fig. 1, the crystal structure of the title compound consists of two independent neutral mononuclear CoII complex molecules and one water of crystallization. The CoII atoms of the two molecules lie on inversion centers and display an octahedral geometry defined by two carboxylate O atoms of two ketoprofenato ligands and four water molecules. The Co1—Oketoprofenato and Co2—Oketoprofenato bond lengths are 2.134 (2) and 2.064 (2) Å, respectively. The Co—Owater bond lengths range from 2.051 (3) to 2.183 (2) Å. In the ketoprofenato ligands, two benzene rings are not coplanar, the dihedral angles are 70.1 (3) and 121.7 (3) °. A three-dimensional supramolecular network structure is formed through the extended hydrogen bonding interactions between water molecules and carboxylate O atoms (Table 2).