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
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.007 Å
- R factor = 0.053
- wR factor = 0.174
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.80 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - C17 .. 5.48 su PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C18 = ... S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 15
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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).