Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052762/im2040sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052762/im2040Isup2.hkl |
CCDC reference: 672577
The title complex was prepared by the addition of nickel diacetate tetrahydrate (2.49 g, 10 mmol) to a hot aqueous solution of racemic 2-(3-benzoylphenyl)propanoic acid (2.54 g, 10 mmol); the pH was adjusted to 6 with 0.1M sodium hydroxide. The solution was allowed to evaporate at room temperature. Green prismatic crystals separated from the filtered solution after several days. Elemental analysis: calcd. for C32H36NiO11: C 58.63, H 5.54%; found: C 58.52, H 5.69%.
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).
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: ORTEP-II (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Ni(C16H13O3)2(H2O)4]·H2O | Z = 2 |
Mr = 655.32 | F(000) = 688 |
Triclinic, P1 | Dx = 1.415 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.559 (2) Å | Cell parameters from 7166 reflections |
b = 8.851 (2) Å | θ = 3.2–27.5° |
c = 21.875 (4) Å | µ = 0.69 mm−1 |
α = 92.05 (3)° | T = 295 K |
β = 99.78 (3)° | Sheet, pale green |
γ = 108.90 (3)° | 0.34 × 0.25 × 0.19 mm |
V = 1537.7 (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 = 27.6°, θmin = 3.2° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −11→11 |
Tmin = 0.799, Tmax = 0.880 | 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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.174 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0853P)2] where P = (Fo2 + 2Fc2)/3 |
7032 reflections | (Δ/σ)max < 0.001 |
432 parameters | Δρmax = 0.78 e Å−3 |
15 restraints | Δρmin = −0.74 e Å−3 |
[Ni(C16H13O3)2(H2O)4]·H2O | γ = 108.90 (3)° |
Mr = 655.32 | V = 1537.7 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.559 (2) Å | Mo Kα radiation |
b = 8.851 (2) Å | µ = 0.69 mm−1 |
c = 21.875 (4) Å | T = 295 K |
α = 92.05 (3)° | 0.34 × 0.25 × 0.19 mm |
β = 99.78 (3)° |
Rigaku R-AXIS RAPID diffractometer | 7032 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 4192 reflections with I > 2σ(I) |
Tmin = 0.799, Tmax = 0.880 | Rint = 0.049 |
15351 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 15 restraints |
wR(F2) = 0.174 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.14 | Δρmax = 0.78 e Å−3 |
7032 reflections | Δρmin = −0.74 e Å−3 |
432 parameters |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.0000 | 0.5000 | 0.5000 | 0.02982 (19) | |
Ni2 | 0.5000 | 0.0000 | 0.5000 | 0.02956 (19) | |
O1W | 0.0183 (3) | 0.7333 (3) | 0.48051 (12) | 0.0373 (6) | |
H1W1 | −0.054 (4) | 0.715 (5) | 0.4469 (11) | 0.056* | |
H1W2 | 0.104 (3) | 0.813 (3) | 0.4787 (17) | 0.056* | |
O2W | −0.1773 (3) | 0.5045 (3) | 0.55378 (13) | 0.0374 (6) | |
H2W1 | −0.266 (3) | 0.423 (3) | 0.548 (2) | 0.056* | |
H2W2 | −0.203 (5) | 0.588 (2) | 0.550 (2) | 0.056* | |
O3W | 0.3556 (4) | −0.0891 (3) | 0.56486 (13) | 0.0425 (7) | |
H3W1 | 0.329 (5) | −0.021 (3) | 0.5854 (19) | 0.064* | |
H3W2 | 0.295 (5) | −0.1834 (18) | 0.569 (2) | 0.064* | |
O4W | 0.5285 (3) | 0.2437 (3) | 0.53314 (12) | 0.0333 (6) | |
H4W1 | 0.449 (3) | 0.251 (5) | 0.5061 (12) | 0.050* | |
H4W2 | 0.497 (4) | 0.218 (5) | 0.5668 (10) | 0.050* | |
O5W | −0.3714 (5) | −0.1696 (4) | 0.36447 (13) | 0.0526 (8) | |
H5W1 | −0.420 (6) | −0.176 (6) | 0.3269 (9) | 0.079* | |
H5W2 | −0.313 (6) | −0.231 (5) | 0.3679 (19) | 0.079* | |
O1 | −0.2010 (3) | 0.3951 (3) | 0.42308 (11) | 0.0307 (6) | |
O2 | −0.2224 (4) | 0.6112 (3) | 0.38158 (13) | 0.0524 (8) | |
O3 | −0.4238 (5) | −0.1841 (4) | 0.23630 (14) | 0.0631 (10) | |
O4 | 0.2831 (3) | −0.0170 (3) | 0.43855 (12) | 0.0388 (6) | |
O5 | 0.2942 (4) | 0.2352 (3) | 0.43586 (12) | 0.0402 (6) | |
O6 | 0.1073 (5) | −0.1320 (4) | 0.08882 (14) | 0.0726 (11) | |
C1 | −0.2702 (5) | 0.4638 (4) | 0.38376 (16) | 0.0315 (8) | |
C2 | −0.4235 (5) | 0.3574 (4) | 0.33630 (15) | 0.0315 (8) | |
H2 | −0.4809 | 0.2635 | 0.3564 | 0.038* | |
C3 | −0.5476 (5) | 0.4426 (5) | 0.31537 (18) | 0.0419 (10) | |
H3A | −0.5800 | 0.4813 | 0.3511 | 0.063* | |
H3B | −0.6454 | 0.3693 | 0.2885 | 0.063* | |
H3C | −0.4963 | 0.5314 | 0.2932 | 0.063* | |
C4 | −0.3642 (5) | 0.2982 (4) | 0.28058 (16) | 0.0332 (8) | |
C5 | −0.4119 (5) | 0.1371 (4) | 0.26247 (16) | 0.0327 (8) | |
H5 | −0.4775 | 0.0633 | 0.2850 | 0.039* | |
C6 | −0.3628 (5) | 0.0826 (5) | 0.21024 (17) | 0.0385 (9) | |
C7 | −0.2675 (6) | 0.1917 (5) | 0.17658 (19) | 0.0492 (11) | |
H7 | −0.2376 | 0.1563 | 0.1412 | 0.059* | |
C8 | −0.2167 (7) | 0.3521 (5) | 0.1949 (2) | 0.0621 (14) | |
H8 | −0.1492 | 0.4258 | 0.1728 | 0.074* | |
C9 | −0.2661 (6) | 0.4049 (5) | 0.2466 (2) | 0.0501 (11) | |
H9 | −0.2324 | 0.5143 | 0.2585 | 0.060* | |
C10 | −0.3988 (5) | −0.0920 (5) | 0.19615 (18) | 0.0408 (10) | |
C11 | −0.3997 (6) | −0.1565 (5) | 0.13194 (19) | 0.0445 (10) | |
C12 | −0.4931 (7) | −0.1245 (6) | 0.0799 (2) | 0.0632 (14) | |
H12 | −0.5546 | −0.0563 | 0.0837 | 0.076* | |
C13 | −0.4960 (9) | −0.1930 (7) | 0.0220 (2) | 0.0818 (19) | |
H13 | −0.5623 | −0.1734 | −0.0130 | 0.098* | |
C14 | −0.4026 (10) | −0.2894 (7) | 0.0156 (3) | 0.087 (2) | |
H14 | −0.4022 | −0.3323 | −0.0238 | 0.105* | |
C15 | −0.3110 (9) | −0.3221 (7) | 0.0665 (3) | 0.0822 (19) | |
H15 | −0.2477 | −0.3882 | 0.0620 | 0.099* | |
C16 | −0.3097 (7) | −0.2590 (6) | 0.1254 (2) | 0.0602 (13) | |
H16 | −0.2489 | −0.2851 | 0.1604 | 0.072* | |
C17 | 0.2332 (5) | 0.0918 (4) | 0.41577 (16) | 0.0326 (8) | |
C18 | 0.0788 (5) | 0.0336 (5) | 0.36172 (17) | 0.0417 (10) | |
H18 | −0.0072 | −0.0492 | 0.3779 | 0.050* | |
C19 | 0.0037 (6) | 0.1592 (6) | 0.3454 (2) | 0.0547 (12) | |
H19A | −0.0273 | 0.1974 | 0.3816 | 0.082* | |
H19B | −0.0945 | 0.1151 | 0.3132 | 0.082* | |
H19C | 0.0842 | 0.2467 | 0.3309 | 0.082* | |
C20 | 0.1152 (5) | −0.0518 (5) | 0.30667 (17) | 0.0385 (9) | |
C21 | 0.1131 (5) | 0.0027 (5) | 0.24809 (17) | 0.0388 (9) | |
H21 | 0.0941 | 0.0992 | 0.2421 | 0.047* | |
C22 | 0.1386 (5) | −0.0820 (5) | 0.19768 (18) | 0.0394 (9) | |
C23 | 0.1690 (6) | −0.2258 (5) | 0.2073 (2) | 0.0513 (12) | |
H23 | 0.1865 | −0.2847 | 0.1747 | 0.062* | |
C24 | 0.1727 (7) | −0.2792 (5) | 0.2655 (2) | 0.0572 (13) | |
H24 | 0.1937 | −0.3747 | 0.2718 | 0.069* | |
C25 | 0.1461 (6) | −0.1956 (5) | 0.3148 (2) | 0.0495 (11) | |
H25 | 0.1489 | −0.2352 | 0.3536 | 0.059* | |
C26 | 0.1263 (6) | −0.0346 (5) | 0.13258 (19) | 0.0492 (11) | |
C27 | 0.1325 (6) | 0.1312 (5) | 0.11962 (17) | 0.0441 (10) | |
C28 | 0.2545 (6) | 0.2649 (5) | 0.15325 (19) | 0.0510 (11) | |
H28 | 0.3303 | 0.2525 | 0.1869 | 0.061* | |
C29 | 0.2646 (7) | 0.4157 (6) | 0.1374 (2) | 0.0633 (14) | |
H29 | 0.3485 | 0.5050 | 0.1597 | 0.076* | |
C30 | 0.1523 (8) | 0.4347 (7) | 0.0891 (2) | 0.0710 (16) | |
H30 | 0.1579 | 0.5374 | 0.0792 | 0.085* | |
C31 | 0.0293 (7) | 0.3025 (6) | 0.0546 (2) | 0.0621 (14) | |
H31 | −0.0473 | 0.3160 | 0.0215 | 0.074* | |
C32 | 0.0214 (6) | 0.1525 (6) | 0.06945 (18) | 0.0545 (12) | |
H32 | −0.0594 | 0.0634 | 0.0457 | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0269 (4) | 0.0246 (3) | 0.0340 (4) | 0.0048 (3) | 0.0027 (3) | 0.0027 (3) |
Ni2 | 0.0262 (4) | 0.0252 (3) | 0.0336 (4) | 0.0051 (3) | 0.0029 (3) | 0.0031 (3) |
O1W | 0.0306 (16) | 0.0254 (12) | 0.0461 (15) | −0.0004 (11) | −0.0008 (12) | 0.0090 (11) |
O2W | 0.0320 (15) | 0.0278 (13) | 0.0512 (16) | 0.0068 (11) | 0.0119 (12) | −0.0005 (12) |
O3W | 0.0550 (19) | 0.0256 (13) | 0.0459 (16) | 0.0042 (13) | 0.0253 (13) | 0.0047 (12) |
O4W | 0.0323 (15) | 0.0258 (12) | 0.0385 (14) | 0.0057 (11) | 0.0063 (11) | 0.0013 (11) |
O5W | 0.079 (3) | 0.0448 (17) | 0.0418 (16) | 0.0346 (17) | 0.0068 (15) | −0.0009 (14) |
O1 | 0.0274 (14) | 0.0263 (12) | 0.0338 (13) | 0.0072 (10) | −0.0031 (10) | 0.0036 (10) |
O2 | 0.053 (2) | 0.0290 (14) | 0.0599 (18) | 0.0078 (13) | −0.0205 (15) | 0.0109 (13) |
O3 | 0.108 (3) | 0.0454 (17) | 0.0456 (18) | 0.0350 (19) | 0.0218 (18) | 0.0069 (15) |
O4 | 0.0310 (15) | 0.0298 (13) | 0.0482 (15) | 0.0096 (11) | −0.0108 (12) | 0.0042 (12) |
O5 | 0.0396 (16) | 0.0349 (14) | 0.0448 (15) | 0.0143 (12) | 0.0005 (12) | 0.0057 (12) |
O6 | 0.111 (3) | 0.068 (2) | 0.0395 (17) | 0.036 (2) | 0.0074 (18) | −0.0136 (17) |
C1 | 0.031 (2) | 0.0272 (17) | 0.0331 (18) | 0.0061 (15) | 0.0053 (15) | 0.0014 (15) |
C2 | 0.030 (2) | 0.0313 (18) | 0.0288 (17) | 0.0076 (15) | 0.0005 (14) | 0.0008 (15) |
C3 | 0.036 (2) | 0.043 (2) | 0.043 (2) | 0.0148 (18) | −0.0045 (17) | −0.0045 (18) |
C4 | 0.031 (2) | 0.0343 (19) | 0.0303 (18) | 0.0085 (16) | 0.0012 (15) | 0.0004 (16) |
C5 | 0.034 (2) | 0.0369 (19) | 0.0276 (17) | 0.0139 (17) | 0.0031 (15) | 0.0030 (15) |
C6 | 0.036 (2) | 0.041 (2) | 0.036 (2) | 0.0106 (18) | 0.0050 (16) | 0.0010 (17) |
C7 | 0.061 (3) | 0.048 (2) | 0.040 (2) | 0.016 (2) | 0.020 (2) | 0.0010 (19) |
C8 | 0.078 (4) | 0.046 (3) | 0.055 (3) | 0.001 (2) | 0.032 (3) | 0.003 (2) |
C9 | 0.057 (3) | 0.036 (2) | 0.050 (2) | 0.004 (2) | 0.015 (2) | −0.0025 (19) |
C10 | 0.048 (3) | 0.040 (2) | 0.037 (2) | 0.0189 (19) | 0.0065 (18) | −0.0008 (18) |
C11 | 0.052 (3) | 0.034 (2) | 0.046 (2) | 0.0088 (19) | 0.017 (2) | −0.0015 (18) |
C12 | 0.082 (4) | 0.064 (3) | 0.045 (3) | 0.027 (3) | 0.011 (2) | 0.005 (2) |
C13 | 0.114 (6) | 0.075 (4) | 0.042 (3) | 0.019 (4) | 0.004 (3) | 0.002 (3) |
C14 | 0.132 (6) | 0.058 (3) | 0.057 (3) | 0.002 (4) | 0.040 (4) | −0.017 (3) |
C15 | 0.100 (5) | 0.065 (3) | 0.086 (4) | 0.023 (3) | 0.046 (4) | −0.015 (3) |
C16 | 0.069 (4) | 0.050 (3) | 0.065 (3) | 0.023 (3) | 0.017 (3) | −0.005 (2) |
C17 | 0.028 (2) | 0.039 (2) | 0.0315 (18) | 0.0110 (17) | 0.0079 (15) | 0.0015 (16) |
C18 | 0.046 (3) | 0.047 (2) | 0.0324 (19) | 0.021 (2) | −0.0003 (17) | 0.0012 (18) |
C19 | 0.045 (3) | 0.070 (3) | 0.051 (3) | 0.028 (2) | −0.002 (2) | −0.005 (2) |
C20 | 0.039 (2) | 0.041 (2) | 0.035 (2) | 0.0182 (18) | −0.0020 (16) | −0.0017 (17) |
C21 | 0.038 (2) | 0.039 (2) | 0.038 (2) | 0.0160 (18) | −0.0001 (17) | −0.0057 (17) |
C22 | 0.037 (2) | 0.039 (2) | 0.039 (2) | 0.0131 (18) | 0.0003 (17) | −0.0053 (18) |
C23 | 0.057 (3) | 0.051 (3) | 0.048 (2) | 0.026 (2) | 0.002 (2) | −0.008 (2) |
C24 | 0.073 (4) | 0.045 (2) | 0.058 (3) | 0.031 (2) | 0.002 (2) | −0.007 (2) |
C25 | 0.059 (3) | 0.046 (2) | 0.044 (2) | 0.023 (2) | 0.002 (2) | 0.003 (2) |
C26 | 0.049 (3) | 0.054 (3) | 0.040 (2) | 0.013 (2) | 0.0041 (19) | −0.009 (2) |
C27 | 0.048 (3) | 0.051 (2) | 0.031 (2) | 0.016 (2) | 0.0046 (17) | −0.0027 (18) |
C28 | 0.054 (3) | 0.056 (3) | 0.037 (2) | 0.016 (2) | −0.0021 (19) | −0.002 (2) |
C29 | 0.081 (4) | 0.053 (3) | 0.048 (3) | 0.014 (3) | 0.011 (2) | 0.000 (2) |
C30 | 0.118 (5) | 0.064 (3) | 0.047 (3) | 0.045 (3) | 0.028 (3) | 0.015 (2) |
C31 | 0.081 (4) | 0.077 (3) | 0.036 (2) | 0.040 (3) | 0.004 (2) | 0.004 (2) |
C32 | 0.059 (3) | 0.071 (3) | 0.031 (2) | 0.023 (3) | 0.0002 (19) | −0.006 (2) |
Ni1—O2W | 2.081 (3) | C8—H8 | 0.9300 |
Ni1—O1W | 2.085 (2) | C9—H9 | 0.9300 |
Ni1—O1 | 2.127 (2) | C10—C11 | 1.495 (5) |
Ni2—O3W | 2.051 (3) | C11—C12 | 1.370 (6) |
Ni2—O4 | 2.057 (2) | C11—C16 | 1.384 (6) |
Ni2—O4W | 2.174 (2) | C12—C13 | 1.377 (7) |
Ni1—O2Wi | 2.081 (3) | C12—H12 | 0.9300 |
Ni1—O1Wi | 2.085 (2) | C13—C14 | 1.363 (9) |
Ni1—O1i | 2.127 (2) | C13—H13 | 0.9300 |
Ni2—O3Wii | 2.051 (3) | C14—C15 | 1.347 (9) |
Ni2—O4ii | 2.057 (2) | C14—H14 | 0.9300 |
Ni2—O4Wii | 2.174 (2) | C15—C16 | 1.383 (7) |
O1W—H1W1 | 0.85 (3) | C15—H15 | 0.9300 |
O1W—H1W2 | 0.85 (3) | C16—H16 | 0.9300 |
O2W—H2W1 | 0.85 (3) | C17—C18 | 1.547 (5) |
O2W—H2W2 | 0.84 (3) | C18—C19 | 1.480 (6) |
O3W—H3W1 | 0.85 (4) | C18—C20 | 1.528 (5) |
O3W—H3W2 | 0.85 (4) | C18—H18 | 0.9800 |
O4W—H4W1 | 0.84 (3) | C19—H19A | 0.9600 |
O4W—H4W2 | 0.84 (3) | C19—H19B | 0.9600 |
O5W—H5W1 | 0.85 (2) | C19—H19C | 0.9600 |
O5W—H5W2 | 0.85 (5) | C20—C21 | 1.384 (5) |
O1—C1 | 1.248 (4) | C20—C25 | 1.393 (6) |
O2—C1 | 1.240 (4) | C21—C22 | 1.398 (5) |
O3—C10 | 1.218 (5) | C21—H21 | 0.9300 |
O4—C17 | 1.260 (4) | C22—C23 | 1.395 (6) |
O5—C17 | 1.237 (4) | C22—C26 | 1.495 (6) |
O6—C26 | 1.218 (5) | C23—C24 | 1.372 (6) |
C1—C2 | 1.534 (5) | C23—H23 | 0.9300 |
C2—C3 | 1.512 (5) | C24—C25 | 1.378 (6) |
C2—C4 | 1.534 (5) | C24—H24 | 0.9300 |
C2—H2 | 0.9800 | C25—H25 | 0.9300 |
C3—H3A | 0.9600 | C26—C27 | 1.490 (6) |
C3—H3B | 0.9600 | C27—C28 | 1.381 (6) |
C3—H3C | 0.9600 | C27—C32 | 1.386 (6) |
C4—C5 | 1.373 (5) | C28—C29 | 1.370 (7) |
C4—C9 | 1.378 (6) | C28—H28 | 0.9300 |
C5—C6 | 1.403 (5) | C29—C30 | 1.357 (7) |
C5—H5 | 0.9300 | C29—H29 | 0.9300 |
C6—C7 | 1.372 (6) | C30—C31 | 1.385 (8) |
C6—C10 | 1.484 (5) | C30—H30 | 0.9300 |
C7—C8 | 1.366 (6) | C31—C32 | 1.361 (7) |
C7—H7 | 0.9300 | C31—H31 | 0.9300 |
C8—C9 | 1.388 (6) | C32—H32 | 0.9300 |
O2W—Ni1—O1W | 88.29 (11) | C8—C9—H9 | 119.4 |
O2W—Ni1—O1Wi | 91.71 (11) | O3—C10—C6 | 121.4 (3) |
O2W—Ni1—O1 | 88.56 (10) | O3—C10—C11 | 118.9 (3) |
O1W—Ni1—O1 | 93.12 (10) | C6—C10—C11 | 119.7 (4) |
O2W—Ni1—O1i | 91.44 (10) | C12—C11—C16 | 119.1 (4) |
O1W—Ni1—O1i | 86.88 (10) | C12—C11—C10 | 122.3 (4) |
O3W—Ni2—O4ii | 91.44 (12) | C16—C11—C10 | 118.5 (4) |
O3W—Ni2—O4 | 88.56 (12) | C11—C12—C13 | 120.1 (5) |
O3W—Ni2—O4W | 90.55 (10) | C11—C12—H12 | 119.9 |
O4—Ni2—O4W | 90.65 (10) | C13—C12—H12 | 119.9 |
O3W—Ni2—O4Wii | 89.45 (10) | C14—C13—C12 | 120.6 (6) |
O4—Ni2—O4Wii | 89.35 (10) | C14—C13—H13 | 119.7 |
O2Wi—Ni1—O2W | 180.000 (1) | C12—C13—H13 | 119.7 |
O2Wi—Ni1—O1W | 91.71 (11) | C15—C14—C13 | 119.7 (5) |
O2Wi—Ni1—O1Wi | 88.29 (11) | C15—C14—H14 | 120.2 |
O1W—Ni1—O1Wi | 180.000 (1) | C13—C14—H14 | 120.2 |
O2Wi—Ni1—O1 | 91.44 (10) | C14—C15—C16 | 121.0 (6) |
O1Wi—Ni1—O1 | 86.88 (10) | C14—C15—H15 | 119.5 |
O2Wi—Ni1—O1i | 88.56 (10) | C16—C15—H15 | 119.5 |
O1Wi—Ni1—O1i | 93.12 (10) | C15—C16—C11 | 119.4 (5) |
O1—Ni1—O1i | 180.000 (1) | C15—C16—H16 | 120.3 |
O3Wii—Ni2—O3W | 180.000 (1) | C11—C16—H16 | 120.3 |
O3Wii—Ni2—O4ii | 88.56 (12) | O5—C17—O4 | 124.2 (3) |
O3Wii—Ni2—O4 | 91.44 (12) | O5—C17—C18 | 120.4 (3) |
O4ii—Ni2—O4 | 180.000 (1) | O4—C17—C18 | 115.3 (3) |
O3Wii—Ni2—O4W | 89.45 (10) | C19—C18—C20 | 115.0 (3) |
O4ii—Ni2—O4W | 89.35 (10) | C19—C18—C17 | 113.1 (3) |
O3Wii—Ni2—O4Wii | 90.55 (10) | C20—C18—C17 | 111.6 (3) |
O4ii—Ni2—O4Wii | 90.65 (10) | C19—C18—H18 | 105.4 |
O4W—Ni2—O4Wii | 180.000 (1) | C20—C18—H18 | 105.4 |
Ni1—O1W—H1W1 | 101 (3) | C17—C18—H18 | 105.4 |
Ni1—O1W—H1W2 | 130 (3) | C18—C19—H19A | 109.5 |
H1W1—O1W—H1W2 | 111 (4) | C18—C19—H19B | 109.5 |
Ni1—O2W—H2W1 | 116 (3) | H19A—C19—H19B | 109.5 |
Ni1—O2W—H2W2 | 111 (3) | C18—C19—H19C | 109.5 |
H2W1—O2W—H2W2 | 110 (3) | H19A—C19—H19C | 109.5 |
Ni2—O3W—H3W1 | 116 (3) | H19B—C19—H19C | 109.5 |
Ni2—O3W—H3W2 | 131 (3) | C21—C20—C25 | 117.7 (4) |
H3W1—O3W—H3W2 | 110 (4) | C21—C20—C18 | 123.6 (3) |
Ni2—O4W—H4W1 | 95 (3) | C25—C20—C18 | 118.6 (4) |
Ni2—O4W—H4W2 | 94 (3) | C20—C21—C22 | 122.5 (4) |
H4W1—O4W—H4W2 | 111 (4) | C20—C21—H21 | 118.8 |
H5W1—O5W—H5W2 | 110 (4) | C22—C21—H21 | 118.8 |
C1—O1—Ni1 | 128.4 (2) | C23—C22—C21 | 118.4 (4) |
C17—O4—Ni2 | 130.0 (2) | C23—C22—C26 | 116.9 (4) |
O2—C1—O1 | 123.7 (3) | C21—C22—C26 | 124.7 (4) |
O2—C1—C2 | 119.2 (3) | C24—C23—C22 | 119.3 (4) |
O1—C1—C2 | 117.1 (3) | C24—C23—H23 | 120.4 |
C3—C2—C1 | 112.2 (3) | C22—C23—H23 | 120.4 |
C3—C2—C4 | 111.2 (3) | C23—C24—C25 | 122.0 (4) |
C1—C2—C4 | 109.4 (3) | C23—C24—H24 | 119.0 |
C3—C2—H2 | 108.0 | C25—C24—H24 | 119.0 |
C1—C2—H2 | 108.0 | C24—C25—C20 | 120.2 (4) |
C4—C2—H2 | 108.0 | C24—C25—H25 | 119.9 |
C2—C3—H3A | 109.5 | C20—C25—H25 | 119.9 |
C2—C3—H3B | 109.5 | O6—C26—C27 | 118.6 (4) |
H3A—C3—H3B | 109.5 | O6—C26—C22 | 120.5 (4) |
C2—C3—H3C | 109.5 | C27—C26—C22 | 120.9 (3) |
H3A—C3—H3C | 109.5 | C28—C27—C32 | 118.8 (4) |
H3B—C3—H3C | 109.5 | C28—C27—C26 | 121.8 (4) |
C5—C4—C9 | 118.5 (3) | C32—C27—C26 | 119.2 (4) |
C5—C4—C2 | 120.5 (3) | C29—C28—C27 | 120.5 (4) |
C9—C4—C2 | 121.0 (3) | C29—C28—H28 | 119.7 |
C4—C5—C6 | 120.7 (4) | C27—C28—H28 | 119.7 |
C4—C5—H5 | 119.7 | C30—C29—C28 | 120.0 (5) |
C6—C5—H5 | 119.7 | C30—C29—H29 | 120.0 |
C7—C6—C5 | 119.6 (4) | C28—C29—H29 | 120.0 |
C7—C6—C10 | 120.6 (4) | C29—C30—C31 | 120.5 (5) |
C5—C6—C10 | 119.4 (4) | C29—C30—H30 | 119.7 |
C8—C7—C6 | 120.2 (4) | C31—C30—H30 | 119.7 |
C8—C7—H7 | 119.9 | C32—C31—C30 | 119.5 (5) |
C6—C7—H7 | 119.9 | C32—C31—H31 | 120.2 |
C7—C8—C9 | 119.8 (4) | C30—C31—H31 | 120.2 |
C7—C8—H8 | 120.1 | C31—C32—C27 | 120.6 (4) |
C9—C8—H8 | 120.1 | C31—C32—H32 | 119.7 |
C4—C9—C8 | 121.3 (4) | C27—C32—H32 | 119.7 |
C4—C9—H9 | 119.4 | ||
O2Wi—Ni1—O1—C1 | −91.4 (3) | C13—C14—C15—C16 | −0.2 (10) |
O2W—Ni1—O1—C1 | 88.6 (3) | C14—C15—C16—C11 | −2.1 (9) |
O1W—Ni1—O1—C1 | 0.4 (3) | C12—C11—C16—C15 | 2.3 (8) |
O1Wi—Ni1—O1—C1 | −179.6 (3) | C10—C11—C16—C15 | 178.9 (5) |
O3Wii—Ni2—O4—C17 | −67.2 (3) | Ni2—O4—C17—O5 | −14.4 (6) |
O3W—Ni2—O4—C17 | 112.8 (3) | Ni2—O4—C17—C18 | 169.2 (3) |
O4W—Ni2—O4—C17 | 22.3 (3) | O5—C17—C18—C19 | −8.5 (6) |
O4Wii—Ni2—O4—C17 | −157.7 (3) | O4—C17—C18—C19 | 168.1 (4) |
Ni1—O1—C1—O2 | 4.7 (6) | O5—C17—C18—C20 | 123.0 (4) |
Ni1—O1—C1—C2 | −174.8 (2) | O4—C17—C18—C20 | −60.5 (5) |
O2—C1—C2—C3 | −29.9 (5) | C19—C18—C20—C21 | 13.1 (6) |
O1—C1—C2—C3 | 149.7 (3) | C17—C18—C20—C21 | −117.4 (4) |
O2—C1—C2—C4 | 94.0 (4) | C19—C18—C20—C25 | −164.4 (4) |
O1—C1—C2—C4 | −86.4 (4) | C17—C18—C20—C25 | 65.1 (5) |
C3—C2—C4—C5 | −110.6 (4) | C25—C20—C21—C22 | 0.8 (6) |
C1—C2—C4—C5 | 124.9 (4) | C18—C20—C21—C22 | −176.7 (4) |
C3—C2—C4—C9 | 67.6 (5) | C20—C21—C22—C23 | −0.7 (6) |
C1—C2—C4—C9 | −57.0 (5) | C20—C21—C22—C26 | 175.7 (4) |
C9—C4—C5—C6 | −0.4 (6) | C21—C22—C23—C24 | 0.1 (7) |
C2—C4—C5—C6 | 177.8 (3) | C26—C22—C23—C24 | −176.6 (4) |
C4—C5—C6—C7 | −0.7 (6) | C22—C23—C24—C25 | 0.4 (8) |
C4—C5—C6—C10 | 172.8 (4) | C23—C24—C25—C20 | −0.3 (8) |
C5—C6—C7—C8 | 1.9 (7) | C21—C20—C25—C24 | −0.3 (7) |
C10—C6—C7—C8 | −171.5 (4) | C18—C20—C25—C24 | 177.4 (4) |
C6—C7—C8—C9 | −2.0 (8) | C23—C22—C26—O6 | 15.3 (7) |
C5—C4—C9—C8 | 0.3 (7) | C21—C22—C26—O6 | −161.2 (4) |
C2—C4—C9—C8 | −177.9 (4) | C23—C22—C26—C27 | −166.2 (4) |
C7—C8—C9—C4 | 0.9 (8) | C21—C22—C26—C27 | 17.3 (7) |
C7—C6—C10—O3 | 151.8 (5) | O6—C26—C27—C28 | −133.4 (5) |
C5—C6—C10—O3 | −21.6 (6) | C22—C26—C27—C28 | 48.1 (7) |
C7—C6—C10—C11 | −26.3 (6) | O6—C26—C27—C32 | 41.5 (7) |
C5—C6—C10—C11 | 160.3 (4) | C22—C26—C27—C32 | −137.0 (4) |
O3—C10—C11—C12 | 129.5 (5) | C32—C27—C28—C29 | 0.3 (7) |
C6—C10—C11—C12 | −52.4 (6) | C26—C27—C28—C29 | 175.3 (5) |
O3—C10—C11—C16 | −47.0 (6) | C27—C28—C29—C30 | 1.3 (8) |
C6—C10—C11—C16 | 131.1 (4) | C28—C29—C30—C31 | −1.6 (8) |
C16—C11—C12—C13 | −0.4 (8) | C29—C30—C31—C32 | 0.1 (8) |
C10—C11—C12—C13 | −176.8 (5) | C30—C31—C32—C27 | 1.5 (8) |
C11—C12—C13—C14 | −1.9 (9) | C28—C27—C32—C31 | −1.7 (7) |
C12—C13—C14—C15 | 2.2 (10) | C26—C27—C32—C31 | −176.8 (4) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O2 | 0.85 (3) | 1.82 (3) | 2.640 (4) | 162 (4) |
O2W—H2W1···O4Wiii | 0.85 (3) | 1.92 (3) | 2.766 (4) | 177 (4) |
O2W—H2W2···O5i | 0.84 (3) | 1.99 (3) | 2.809 (4) | 162 (4) |
O3W—H3W1···O5Wiv | 0.85 (4) | 1.88 (4) | 2.669 (4) | 155 (4) |
O3W—H3W2···O1iv | 0.85 (4) | 1.81 (2) | 2.647 (4) | 169 (4) |
O4W—H4W1···O5 | 0.84 (3) | 1.82 (3) | 2.645 (4) | 166 (4) |
O4W—H4W2···O5Wiv | 0.84 (3) | 1.97 (3) | 2.795 (4) | 166 (3) |
O5W—H5W1···O3 | 0.85 (2) | 1.98 (3) | 2.755 (4) | 152 (5) |
O5W—H5W2···O2v | 0.85 (5) | 1.82 (5) | 2.651 (4) | 168 (6) |
Symmetry codes: (i) −x, −y+1, −z+1; (iii) x−1, y, z; (iv) −x, −y, −z+1; (v) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C16H13O3)2(H2O)4]·H2O |
Mr | 655.32 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 8.559 (2), 8.851 (2), 21.875 (4) |
α, β, γ (°) | 92.05 (3), 99.78 (3), 108.90 (3) |
V (Å3) | 1537.7 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.69 |
Crystal size (mm) | 0.34 × 0.25 × 0.19 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.799, 0.880 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15351, 7032, 4192 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.652 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.174, 1.14 |
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) | 0.78, −0.74 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-II (Johnson, 1976).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O2 | 0.85 (3) | 1.82 (3) | 2.640 (4) | 162 (4) |
O2W—H2W1···O4Wi | 0.85 (3) | 1.92 (3) | 2.766 (4) | 177 (4) |
O2W—H2W2···O5ii | 0.84 (3) | 1.99 (3) | 2.809 (4) | 162 (4) |
O3W—H3W1···O5Wiii | 0.85 (4) | 1.88 (4) | 2.669 (4) | 155 (4) |
O3W—H3W2···O1iii | 0.85 (4) | 1.812 (17) | 2.647 (4) | 169 (4) |
O4W—H4W1···O5 | 0.84 (3) | 1.82 (3) | 2.645 (4) | 166 (4) |
O4W—H4W2···O5Wiii | 0.84 (3) | 1.97 (3) | 2.795 (4) | 166 (3) |
O5W—H5W1···O3 | 0.85 (2) | 1.98 (3) | 2.755 (4) | 152 (5) |
O5W—H5W2···O2iv | 0.85 (5) | 1.82 (5) | 2.651 (4) | 168 (6) |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+1; (iii) −x, −y, −z+1; (iv) x, y−1, z. |
2-(3-benzoylphenyl)propanoic acid is known as a nonsteroidal anti-inflamatory drug, but there is little information on the structure of its metal complexes (Tahir et al., 1997). The preceeding report (Zhang et al., 2007) details the synthesis and crystal structure of tetraaquabis[2-(3-benzoylphenyl)propanoato-κO] cobalt(II) monohydrate. Replacing cobalt by nickel in a similar reaction leads to the formation of the title complex, (I), (Fig. 1). Similar structural descriptions of the CoII apply to the isomorphous complex.
As illustrated in Fig. 1, the crystal structure of the title compound consists of two crystallographically independent neutral mononuclear NiII complex molecules and one water of crystallization. The NiII atoms of the two molecules are situated at crystallographic centers of inversion and display an octahedral geometry defined by two carboxylate O atoms of two ketoprofenato ligands and four water molecules. A three-dimensional supramolecular network structure is formed through the extended hydrogen bonding interactions between water molecules and carboxylate O atoms (Table 1).