Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040043/tk6292sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040043/tk6292Isup2.hkl |
CCDC reference: 296684
The complex was obtained by reacting NiII nitrate with 2-benzyl-1,3-diphenylpropane-1,3-dione ligand in ethanol, in the presence of triethylamine. The obtained precipitate was redissolved in hot pyridine. Slow evaporation of the pyridine solution yielded the bis(pyridine) adduct as small yellow irregular prisms.
The H atoms were included in the riding-model approximation with C—H(aromatic) = 0.93 Å, C—H(methylene) = 0.97 Å and Uiso(H) = 1.2Ueq(C). One of the benzyl groups, with the ispo-C117 atom, was found to be disordered over two sites, with relative occupancies fixed at 0.53 for C118–C122 and 0.47 for C123–C127, respectively. The values of the occupation parameters were determined in the early stages of refinement and were later fixed at these values. The displacement parameters of the non-H atoms belonging to the minor component of the disorder were constrained to be equal to those of the major component.
Data collection: STADI4 (Stoe & Cie, 1995); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) Mercury (Version 1.2.1; Bruno et al., 2002) RasTop (Valadon, 2004) and POVRay (Version 3.6; Persistence of Vision, 2004); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Ni(C22H17O2)2(C5H5N)2] | F(000) = 1768 |
Mr = 843.60 | Dx = 1.279 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 36 reflections |
a = 10.8449 (11) Å | θ = 10.0–13.6° |
b = 15.2308 (16) Å | µ = 0.49 mm−1 |
c = 26.770 (2) Å | T = 295 K |
β = 97.900 (8)° | Prism, yellow |
V = 4379.8 (7) Å3 | 0.2 × 0.1 × 0.1 mm |
Z = 4 |
Philips PW1100 diffractometer | 3236 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.062 |
Planar Graphite monochromator | θmax = 27.0°, θmin = 2.0° |
ω scans | h = −13→13 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→19 |
Tmin = 0.879, Tmax = 0.946 | l = 0→34 |
9686 measured reflections | 3 standard reflections every 60 min |
9483 independent reflections | intensity decay: 6.5% |
Refinement on F2 | 18 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.070 | w = 1/[σ2(Fo2) + (0.0558P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.159 | (Δ/σ)max = 0.007 |
S = 0.95 | Δρmax = 0.37 e Å−3 |
9483 reflections | Δρmin = −0.35 e Å−3 |
596 parameters |
[Ni(C22H17O2)2(C5H5N)2] | V = 4379.8 (7) Å3 |
Mr = 843.60 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.8449 (11) Å | µ = 0.49 mm−1 |
b = 15.2308 (16) Å | T = 295 K |
c = 26.770 (2) Å | 0.2 × 0.1 × 0.1 mm |
β = 97.900 (8)° |
Philips PW1100 diffractometer | 3236 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.062 |
Tmin = 0.879, Tmax = 0.946 | 3 standard reflections every 60 min |
9686 measured reflections | intensity decay: 6.5% |
9483 independent reflections |
R[F2 > 2σ(F2)] = 0.070 | 18 restraints |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 0.95 | Δρmax = 0.37 e Å−3 |
9483 reflections | Δρmin = −0.35 e Å−3 |
596 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ni | 0.24253 (6) | 0.11351 (4) | 0.24548 (2) | 0.0444 (2) | |
O11 | 0.2924 (3) | 0.1020 (2) | 0.17527 (10) | 0.0497 (9) | |
O12 | 0.0747 (3) | 0.0630 (2) | 0.21752 (11) | 0.0505 (9) | |
C11 | 0.2193 (5) | 0.0931 (3) | 0.13454 (17) | 0.0465 (13) | |
C12 | 0.0892 (5) | 0.0805 (3) | 0.12920 (16) | 0.0484 (13) | |
C13 | 0.0275 (4) | 0.0627 (3) | 0.17172 (18) | 0.0469 (12) | |
C14 | 0.0079 (5) | 0.1002 (3) | 0.07858 (16) | 0.0643 (16) | |
H14A | 0.0611 | 0.1023 | 0.0523 | 0.077* | |
H14B | −0.0503 | 0.0522 | 0.0708 | 0.077* | |
C15 | 0.2849 (5) | 0.0963 (3) | 0.08844 (17) | 0.0513 (13) | |
C16 | 0.2705 (6) | 0.0335 (4) | 0.05157 (19) | 0.0755 (18) | |
H16 | 0.2179 | −0.0140 | 0.0543 | 0.091* | |
C17 | 0.3336 (7) | 0.0401 (4) | 0.0104 (2) | 0.091 (2) | |
H17 | 0.3225 | −0.0030 | −0.0144 | 0.109* | |
C18 | 0.4116 (6) | 0.1084 (5) | 0.0053 (2) | 0.093 (2) | |
H18 | 0.4531 | 0.1123 | −0.0228 | 0.112* | |
C19 | 0.4280 (6) | 0.1708 (5) | 0.0419 (2) | 0.100 (2) | |
H19 | 0.4811 | 0.2179 | 0.0390 | 0.119* | |
C110 | 0.3647 (5) | 0.1639 (4) | 0.0840 (2) | 0.0743 (17) | |
H110 | 0.3775 | 0.2062 | 0.1093 | 0.089* | |
C111 | −0.1096 (5) | 0.0398 (3) | 0.16265 (17) | 0.0488 (13) | |
C112 | −0.1952 (5) | 0.0934 (4) | 0.1810 (2) | 0.0652 (15) | |
H112 | −0.1683 | 0.1443 | 0.1983 | 0.078* | |
C113 | −0.3197 (6) | 0.0729 (5) | 0.1741 (2) | 0.0825 (18) | |
H113 | −0.3763 | 0.1108 | 0.1860 | 0.099* | |
C114 | −0.3615 (6) | −0.0029 (5) | 0.1498 (2) | 0.085 (2) | |
H114 | −0.4461 | −0.0159 | 0.1446 | 0.102* | |
C115 | −0.2778 (6) | −0.0590 (5) | 0.1335 (2) | 0.089 (2) | |
H115 | −0.3049 | −0.1118 | 0.1184 | 0.107* | |
C116 | −0.1529 (5) | −0.0377 (4) | 0.13934 (19) | 0.0698 (16) | |
H116 | −0.0968 | −0.0760 | 0.1274 | 0.084* | |
C117 | −0.0644 (5) | 0.1849 (3) | 0.07766 (19) | 0.0748 (10) | |
C118 | −0.1911 (7) | 0.2005 (6) | 0.0670 (3) | 0.0748 (10) | 0.53 |
H118 | −0.2433 | 0.1529 | 0.0584 | 0.090* | 0.53 |
C119 | −0.2431 (7) | 0.2804 (6) | 0.0684 (4) | 0.0748 (10) | 0.53 |
H119 | −0.3290 | 0.2860 | 0.0607 | 0.090* | 0.53 |
C120 | −0.1721 (8) | 0.3542 (5) | 0.0811 (4) | 0.0748 (10) | 0.53 |
H120 | −0.2077 | 0.4098 | 0.0808 | 0.090* | 0.53 |
C121 | −0.0452 (8) | 0.3419 (5) | 0.0943 (4) | 0.0748 (10) | 0.53 |
H121 | 0.0057 | 0.3902 | 0.1029 | 0.090* | 0.53 |
C122 | 0.0062 (7) | 0.2601 (5) | 0.0947 (4) | 0.0748 (10) | 0.53 |
H122 | 0.0903 | 0.2534 | 0.1066 | 0.090* | 0.53 |
C123 | −0.1702 (8) | 0.1791 (6) | 0.0417 (3) | 0.0748 (10) | 0.47 |
H123 | −0.1896 | 0.1285 | 0.0229 | 0.090* | 0.47 |
C124 | −0.2440 (8) | 0.2529 (6) | 0.0359 (4) | 0.0748 (10) | 0.47 |
H124 | −0.3139 | 0.2537 | 0.0115 | 0.090* | 0.47 |
C125 | −0.2157 (10) | 0.3246 (7) | 0.0654 (4) | 0.0748 (10) | 0.47 |
H125 | −0.2706 | 0.3718 | 0.0631 | 0.090* | 0.47 |
C126 | −0.1068 (9) | 0.3288 (6) | 0.0989 (4) | 0.0748 (10) | 0.47 |
H126 | −0.0862 | 0.3788 | 0.1181 | 0.090* | 0.47 |
C127 | −0.0293 (8) | 0.2563 (6) | 0.1029 (4) | 0.0748 (10) | 0.47 |
H127 | 0.0472 | 0.2583 | 0.1234 | 0.090* | 0.47 |
O21 | 0.1849 (3) | 0.1241 (2) | 0.31317 (11) | 0.0505 (9) | |
O22 | 0.4081 (3) | 0.1641 (2) | 0.27606 (11) | 0.0471 (8) | |
C21 | 0.2495 (5) | 0.1405 (3) | 0.35508 (17) | 0.0459 (13) | |
C22 | 0.3795 (5) | 0.1543 (3) | 0.36358 (17) | 0.0502 (13) | |
C23 | 0.4489 (4) | 0.1691 (3) | 0.32305 (18) | 0.0449 (12) | |
C24 | 0.4499 (5) | 0.1429 (3) | 0.41652 (17) | 0.0628 (15) | |
H24A | 0.5035 | 0.1934 | 0.4244 | 0.075* | |
H24B | 0.3901 | 0.1421 | 0.4404 | 0.075* | |
C25 | 0.1716 (5) | 0.1472 (4) | 0.39754 (17) | 0.0519 (13) | |
C26 | 0.1813 (5) | 0.2172 (4) | 0.43050 (19) | 0.0704 (16) | |
H26 | 0.2427 | 0.2594 | 0.4291 | 0.085* | |
C27 | 0.0996 (7) | 0.2245 (6) | 0.4657 (2) | 0.105 (3) | |
H27 | 0.1067 | 0.2717 | 0.4879 | 0.126* | |
C28 | 0.0087 (7) | 0.1634 (7) | 0.4681 (3) | 0.116 (3) | |
H28 | −0.0444 | 0.1680 | 0.4924 | 0.139* | |
C29 | −0.0034 (6) | 0.0967 (5) | 0.4351 (2) | 0.107 (2) | |
H29 | −0.0668 | 0.0559 | 0.4360 | 0.128* | |
C210 | 0.0778 (5) | 0.0880 (4) | 0.3997 (2) | 0.0748 (17) | |
H210 | 0.0683 | 0.0413 | 0.3771 | 0.090* | |
C211 | 0.5832 (5) | 0.1958 (3) | 0.33378 (17) | 0.0502 (13) | |
C212 | 0.6726 (5) | 0.1474 (4) | 0.31432 (19) | 0.0613 (15) | |
H212 | 0.6506 | 0.0961 | 0.2965 | 0.074* | |
C213 | 0.7954 (6) | 0.1752 (5) | 0.3213 (2) | 0.0832 (19) | |
H213 | 0.8549 | 0.1421 | 0.3079 | 0.100* | |
C214 | 0.8308 (7) | 0.2492 (5) | 0.3472 (3) | 0.099 (2) | |
H214 | 0.9141 | 0.2657 | 0.3527 | 0.118* | |
C215 | 0.7432 (7) | 0.2990 (5) | 0.3649 (2) | 0.096 (2) | |
H215 | 0.7663 | 0.3518 | 0.3810 | 0.115* | |
C216 | 0.6195 (5) | 0.2729 (4) | 0.3596 (2) | 0.0760 (18) | |
H216 | 0.5610 | 0.3068 | 0.3732 | 0.091* | |
C217 | 0.5285 (5) | 0.0606 (4) | 0.42393 (18) | 0.0562 (14) | |
C218 | 0.6343 (6) | 0.0567 (5) | 0.4586 (2) | 0.094 (2) | |
H218 | 0.6602 | 0.1074 | 0.4764 | 0.113* | |
C219 | 0.7037 (6) | −0.0184 (5) | 0.4682 (2) | 0.097 (2) | |
H219 | 0.7733 | −0.0187 | 0.4927 | 0.116* | |
C220 | 0.6694 (7) | −0.0913 (5) | 0.4418 (3) | 0.098 (2) | |
H220 | 0.7164 | −0.1424 | 0.4470 | 0.117* | |
C221 | 0.5668 (8) | −0.0897 (5) | 0.4077 (3) | 0.120 (3) | |
H221 | 0.5416 | −0.1409 | 0.3903 | 0.144* | |
C222 | 0.4976 (6) | −0.0144 (4) | 0.3978 (2) | 0.090 (2) | |
H222 | 0.4288 | −0.0150 | 0.3729 | 0.108* | |
N31 | 0.1748 (4) | 0.2431 (3) | 0.22909 (15) | 0.0484 (11) | |
C31 | 0.0786 (5) | 0.2734 (4) | 0.25069 (19) | 0.0631 (15) | |
H31 | 0.0359 | 0.2344 | 0.2688 | 0.076* | |
C32 | 0.2335 (5) | 0.3004 (4) | 0.2035 (2) | 0.0635 (15) | |
H32 | 0.3011 | 0.2810 | 0.1886 | 0.076* | |
C33 | 0.1991 (6) | 0.3875 (4) | 0.1980 (2) | 0.0836 (19) | |
H33 | 0.2414 | 0.4254 | 0.1790 | 0.100* | |
C34 | 0.1015 (7) | 0.4174 (4) | 0.2210 (2) | 0.082 (2) | |
H34 | 0.0777 | 0.4760 | 0.2186 | 0.098* | |
C35 | 0.0405 (6) | 0.3593 (4) | 0.2472 (2) | 0.081 (2) | |
H35 | −0.0267 | 0.3777 | 0.2628 | 0.097* | |
N41 | 0.3159 (4) | −0.0125 (3) | 0.26235 (14) | 0.0473 (10) | |
C41 | 0.4177 (5) | −0.0381 (4) | 0.24427 (18) | 0.0586 (14) | |
H41 | 0.4573 | 0.0025 | 0.2260 | 0.070* | |
C42 | 0.4687 (5) | −0.1202 (4) | 0.2507 (2) | 0.0688 (16) | |
H42 | 0.5401 | −0.1347 | 0.2368 | 0.083* | |
C43 | 0.4127 (6) | −0.1797 (4) | 0.2776 (2) | 0.0717 (17) | |
H43 | 0.4446 | −0.2363 | 0.2826 | 0.086* | |
C44 | 0.3091 (6) | −0.1553 (4) | 0.2973 (2) | 0.0732 (17) | |
H44 | 0.2695 | −0.1949 | 0.3163 | 0.088* | |
C45 | 0.2623 (5) | −0.0707 (4) | 0.28908 (18) | 0.0577 (14) | |
H45 | 0.1913 | −0.0546 | 0.3028 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni | 0.0493 (4) | 0.0469 (4) | 0.0372 (3) | 0.0008 (3) | 0.0067 (3) | −0.0029 (3) |
O11 | 0.056 (2) | 0.054 (2) | 0.0389 (18) | 0.0026 (18) | 0.0072 (16) | −0.0008 (17) |
O12 | 0.053 (2) | 0.061 (2) | 0.0360 (18) | −0.0072 (18) | 0.0018 (16) | 0.0010 (16) |
C11 | 0.069 (4) | 0.035 (3) | 0.037 (3) | −0.003 (3) | 0.009 (3) | 0.004 (2) |
C12 | 0.061 (4) | 0.047 (3) | 0.036 (3) | −0.008 (3) | 0.006 (3) | −0.001 (2) |
C13 | 0.053 (3) | 0.035 (3) | 0.051 (3) | 0.004 (3) | 0.001 (3) | 0.002 (2) |
C14 | 0.075 (4) | 0.076 (4) | 0.041 (3) | −0.023 (3) | 0.004 (3) | 0.004 (3) |
C15 | 0.058 (3) | 0.054 (4) | 0.042 (3) | −0.004 (3) | 0.008 (2) | 0.002 (3) |
C16 | 0.117 (5) | 0.060 (4) | 0.057 (3) | −0.007 (4) | 0.038 (3) | −0.015 (3) |
C17 | 0.135 (6) | 0.076 (5) | 0.069 (4) | 0.003 (5) | 0.044 (4) | −0.027 (4) |
C18 | 0.103 (5) | 0.116 (6) | 0.067 (4) | 0.000 (5) | 0.038 (4) | −0.009 (5) |
C19 | 0.105 (5) | 0.111 (6) | 0.090 (5) | −0.040 (5) | 0.040 (4) | 0.004 (5) |
C110 | 0.084 (4) | 0.080 (5) | 0.064 (4) | −0.022 (4) | 0.030 (3) | −0.013 (3) |
C111 | 0.057 (3) | 0.051 (3) | 0.037 (3) | −0.010 (3) | 0.000 (2) | 0.003 (3) |
C112 | 0.063 (4) | 0.058 (4) | 0.075 (4) | −0.012 (3) | 0.012 (3) | −0.009 (3) |
C113 | 0.069 (5) | 0.085 (5) | 0.098 (5) | 0.002 (4) | 0.024 (4) | −0.003 (4) |
C114 | 0.066 (4) | 0.112 (6) | 0.079 (4) | −0.023 (4) | 0.015 (4) | −0.013 (4) |
C115 | 0.081 (5) | 0.095 (5) | 0.092 (5) | −0.035 (4) | 0.015 (4) | −0.034 (4) |
C116 | 0.067 (4) | 0.071 (4) | 0.073 (4) | −0.012 (3) | 0.013 (3) | −0.020 (3) |
C117 | 0.063 (2) | 0.091 (3) | 0.070 (2) | 0.0053 (19) | 0.0030 (18) | 0.0143 (19) |
C118 | 0.063 (2) | 0.091 (3) | 0.070 (2) | 0.0053 (19) | 0.0030 (18) | 0.0143 (19) |
C119 | 0.063 (2) | 0.091 (3) | 0.070 (2) | 0.0053 (19) | 0.0030 (18) | 0.0143 (19) |
C120 | 0.063 (2) | 0.091 (3) | 0.070 (2) | 0.0053 (19) | 0.0030 (18) | 0.0143 (19) |
C121 | 0.063 (2) | 0.091 (3) | 0.070 (2) | 0.0053 (19) | 0.0030 (18) | 0.0143 (19) |
C122 | 0.063 (2) | 0.091 (3) | 0.070 (2) | 0.0053 (19) | 0.0030 (18) | 0.0143 (19) |
C123 | 0.063 (2) | 0.091 (3) | 0.070 (2) | 0.0053 (19) | 0.0030 (18) | 0.0143 (19) |
C124 | 0.063 (2) | 0.091 (3) | 0.070 (2) | 0.0053 (19) | 0.0030 (18) | 0.0143 (19) |
C125 | 0.063 (2) | 0.091 (3) | 0.070 (2) | 0.0053 (19) | 0.0030 (18) | 0.0143 (19) |
C126 | 0.063 (2) | 0.091 (3) | 0.070 (2) | 0.0053 (19) | 0.0030 (18) | 0.0143 (19) |
C127 | 0.063 (2) | 0.091 (3) | 0.070 (2) | 0.0053 (19) | 0.0030 (18) | 0.0143 (19) |
O21 | 0.055 (2) | 0.061 (2) | 0.0363 (18) | −0.0028 (18) | 0.0077 (16) | −0.0032 (17) |
O22 | 0.054 (2) | 0.051 (2) | 0.0357 (18) | −0.0030 (17) | 0.0020 (16) | −0.0020 (16) |
C21 | 0.058 (3) | 0.043 (3) | 0.036 (3) | 0.005 (3) | 0.003 (3) | 0.002 (2) |
C22 | 0.058 (4) | 0.053 (3) | 0.039 (3) | −0.001 (3) | 0.004 (3) | −0.003 (2) |
C23 | 0.051 (3) | 0.037 (3) | 0.046 (3) | 0.006 (2) | 0.003 (3) | 0.001 (2) |
C24 | 0.069 (4) | 0.070 (4) | 0.048 (3) | −0.003 (3) | 0.002 (3) | −0.011 (3) |
C25 | 0.061 (4) | 0.059 (4) | 0.036 (3) | 0.012 (3) | 0.005 (3) | −0.003 (3) |
C26 | 0.085 (4) | 0.071 (4) | 0.057 (4) | 0.010 (3) | 0.013 (3) | −0.007 (3) |
C27 | 0.114 (6) | 0.141 (8) | 0.062 (4) | 0.036 (5) | 0.025 (4) | −0.030 (5) |
C28 | 0.099 (6) | 0.192 (10) | 0.064 (5) | 0.021 (6) | 0.039 (5) | −0.004 (6) |
C29 | 0.096 (5) | 0.159 (8) | 0.073 (5) | −0.017 (5) | 0.037 (4) | 0.002 (5) |
C210 | 0.077 (4) | 0.091 (5) | 0.061 (4) | −0.001 (4) | 0.026 (3) | −0.010 (3) |
C211 | 0.059 (4) | 0.046 (3) | 0.044 (3) | 0.001 (3) | −0.001 (3) | 0.001 (3) |
C212 | 0.055 (4) | 0.060 (4) | 0.068 (4) | 0.000 (3) | 0.006 (3) | −0.001 (3) |
C213 | 0.057 (4) | 0.107 (6) | 0.086 (5) | 0.011 (4) | 0.014 (3) | 0.003 (4) |
C214 | 0.070 (5) | 0.119 (7) | 0.101 (5) | −0.027 (5) | −0.008 (4) | −0.015 (5) |
C215 | 0.082 (5) | 0.098 (6) | 0.104 (5) | −0.026 (5) | −0.003 (4) | −0.034 (4) |
C216 | 0.065 (4) | 0.078 (5) | 0.083 (4) | −0.001 (4) | 0.005 (3) | −0.017 (4) |
C217 | 0.060 (4) | 0.070 (4) | 0.038 (3) | −0.004 (3) | 0.003 (3) | 0.004 (3) |
C218 | 0.100 (5) | 0.090 (5) | 0.081 (5) | −0.006 (4) | −0.031 (4) | −0.006 (4) |
C219 | 0.087 (5) | 0.091 (6) | 0.100 (5) | 0.008 (5) | −0.033 (4) | 0.021 (5) |
C220 | 0.107 (6) | 0.093 (6) | 0.086 (5) | 0.030 (5) | −0.012 (4) | 0.012 (4) |
C221 | 0.158 (7) | 0.070 (5) | 0.112 (6) | 0.016 (5) | −0.051 (5) | −0.009 (4) |
C222 | 0.104 (5) | 0.070 (5) | 0.084 (4) | 0.016 (4) | −0.035 (4) | −0.005 (4) |
N31 | 0.048 (3) | 0.044 (3) | 0.052 (3) | 0.003 (2) | 0.001 (2) | −0.006 (2) |
C31 | 0.064 (4) | 0.065 (4) | 0.059 (3) | 0.014 (3) | 0.005 (3) | −0.004 (3) |
C32 | 0.053 (4) | 0.058 (4) | 0.079 (4) | −0.006 (3) | 0.008 (3) | −0.011 (3) |
C33 | 0.096 (5) | 0.046 (4) | 0.106 (5) | −0.005 (4) | 0.004 (4) | −0.004 (4) |
C34 | 0.106 (6) | 0.040 (4) | 0.094 (5) | 0.019 (4) | −0.008 (4) | −0.008 (4) |
C35 | 0.088 (5) | 0.077 (5) | 0.075 (4) | 0.042 (4) | 0.002 (4) | −0.010 (4) |
N41 | 0.048 (3) | 0.047 (3) | 0.046 (2) | −0.001 (2) | 0.004 (2) | −0.001 (2) |
C41 | 0.055 (4) | 0.059 (4) | 0.064 (3) | 0.006 (3) | 0.017 (3) | 0.006 (3) |
C42 | 0.073 (4) | 0.071 (5) | 0.064 (3) | 0.014 (4) | 0.017 (3) | 0.000 (4) |
C43 | 0.086 (5) | 0.051 (4) | 0.076 (4) | 0.016 (4) | 0.005 (4) | −0.010 (3) |
C44 | 0.101 (5) | 0.047 (4) | 0.072 (4) | −0.021 (4) | 0.013 (4) | 0.002 (3) |
C45 | 0.060 (4) | 0.054 (4) | 0.061 (3) | −0.009 (3) | 0.014 (3) | −0.003 (3) |
Ni—O11 | 2.033 (3) | C21—C25 | 1.509 (6) |
Ni—O12 | 2.023 (3) | C22—C23 | 1.421 (6) |
Ni—O21 | 2.003 (3) | C22—C24 | 1.525 (6) |
Ni—O22 | 2.021 (3) | C23—C211 | 1.501 (6) |
Ni—N31 | 2.131 (4) | C24—C217 | 1.512 (7) |
Ni—N41 | 2.103 (4) | C24—H24A | 0.9700 |
O11—C11 | 1.264 (5) | C24—H24B | 0.9700 |
O12—C13 | 1.262 (5) | C25—C210 | 1.366 (7) |
C11—C12 | 1.412 (6) | C25—C26 | 1.379 (7) |
C11—C15 | 1.508 (6) | C26—C27 | 1.383 (7) |
C12—C13 | 1.423 (6) | C26—H26 | 0.9300 |
C12—C14 | 1.541 (6) | C27—C28 | 1.363 (9) |
C13—C111 | 1.514 (6) | C27—H27 | 0.9300 |
C14—C117 | 1.508 (7) | C28—C29 | 1.341 (9) |
C14—H14A | 0.9700 | C28—H28 | 0.9300 |
C14—H14B | 0.9700 | C29—C210 | 1.387 (7) |
C15—C110 | 1.361 (7) | C29—H29 | 0.9300 |
C15—C16 | 1.368 (6) | C210—H210 | 0.9300 |
C16—C17 | 1.379 (7) | C211—C212 | 1.376 (6) |
C16—H16 | 0.9300 | C211—C216 | 1.391 (7) |
C17—C18 | 1.359 (8) | C212—C213 | 1.385 (7) |
C17—H17 | 0.9300 | C212—H212 | 0.9300 |
C18—C19 | 1.357 (8) | C213—C214 | 1.350 (8) |
C18—H18 | 0.9300 | C213—H213 | 0.9300 |
C19—C110 | 1.403 (7) | C214—C215 | 1.352 (8) |
C19—H19 | 0.9300 | C214—H214 | 0.9300 |
C110—H110 | 0.9300 | C215—C216 | 1.388 (7) |
C111—C112 | 1.377 (6) | C215—H215 | 0.9300 |
C111—C116 | 1.386 (7) | C216—H216 | 0.9300 |
C112—C113 | 1.373 (7) | C217—C222 | 1.358 (7) |
C112—H112 | 0.9300 | C217—C218 | 1.374 (7) |
C113—C114 | 1.370 (8) | C218—C219 | 1.375 (8) |
C113—H113 | 0.9300 | C218—H218 | 0.9300 |
C114—C115 | 1.361 (8) | C219—C220 | 1.342 (8) |
C114—H114 | 0.9300 | C219—H219 | 0.9300 |
C115—C116 | 1.381 (7) | C220—C221 | 1.338 (8) |
C115—H115 | 0.9300 | C220—H220 | 0.9300 |
C116—H116 | 0.9300 | C221—C222 | 1.376 (8) |
C117—C127 | 1.310 (7) | C221—H221 | 0.9300 |
C117—C123 | 1.395 (7) | C222—H222 | 0.9300 |
C117—C118 | 1.385 (7) | N31—C32 | 1.325 (6) |
C117—C122 | 1.418 (7) | N31—C31 | 1.342 (6) |
C118—C119 | 1.343 (7) | C31—C35 | 1.371 (7) |
C118—H118 | 0.9300 | C31—H31 | 0.9300 |
C119—C120 | 1.378 (7) | C32—C33 | 1.381 (7) |
C119—H119 | 0.9300 | C32—H32 | 0.9300 |
C120—C121 | 1.385 (7) | C33—C34 | 1.373 (8) |
C120—H120 | 0.9300 | C33—H33 | 0.9300 |
C121—C122 | 1.365 (7) | C34—C35 | 1.357 (7) |
C121—H121 | 0.9300 | C34—H34 | 0.9300 |
C122—H122 | 0.9300 | C35—H35 | 0.9300 |
C123—C124 | 1.376 (8) | N41—C41 | 1.324 (5) |
C123—H123 | 0.9300 | N41—C45 | 1.323 (6) |
C124—C125 | 1.359 (8) | C41—C42 | 1.368 (6) |
C124—H124 | 0.9300 | C41—H41 | 0.9300 |
C125—C126 | 1.382 (8) | C42—C43 | 1.354 (7) |
C125—H125 | 0.9300 | C42—H42 | 0.9300 |
C126—C127 | 1.382 (8) | C43—C44 | 1.358 (7) |
C126—H126 | 0.9300 | C43—H43 | 0.9300 |
C127—H127 | 0.9300 | C44—C45 | 1.391 (7) |
O21—C21 | 1.263 (5) | C44—H44 | 0.9300 |
O22—C23 | 1.277 (5) | C45—H45 | 0.9300 |
C21—C22 | 1.413 (6) | ||
O11—Ni—O12 | 88.01 (12) | C23—O22—Ni | 126.2 (3) |
O11—Ni—O21 | 177.25 (13) | O21—C21—C22 | 126.3 (4) |
O11—Ni—O22 | 94.19 (12) | O21—C21—C25 | 112.5 (4) |
O11—Ni—N31 | 91.01 (14) | C22—C21—C25 | 121.2 (4) |
O11—Ni—N41 | 88.79 (14) | C21—C22—C23 | 121.5 (4) |
O12—Ni—O21 | 89.34 (12) | C21—C22—C24 | 119.6 (4) |
O12—Ni—O22 | 177.80 (12) | C23—C22—C24 | 118.5 (5) |
O12—Ni—N31 | 90.49 (14) | O22—C23—C22 | 126.5 (4) |
O12—Ni—N41 | 91.58 (14) | O22—C23—C211 | 113.6 (4) |
O21—Ni—O22 | 88.47 (12) | C22—C23—C211 | 119.9 (4) |
O21—Ni—N31 | 88.30 (14) | C217—C24—C22 | 114.7 (4) |
O21—Ni—N41 | 92.00 (14) | C217—C24—H24A | 108.6 |
O22—Ni—N31 | 89.55 (14) | C22—C24—H24A | 108.6 |
O22—Ni—N41 | 88.39 (13) | C217—C24—H24B | 108.6 |
N31—Ni—N41 | 177.91 (16) | C22—C24—H24B | 108.6 |
C11—O11—Ni | 126.3 (3) | H24A—C24—H24B | 107.6 |
C13—O12—Ni | 125.8 (3) | C210—C25—C26 | 118.4 (5) |
O11—C11—C12 | 127.0 (4) | C210—C25—C21 | 118.9 (5) |
O11—C11—C15 | 113.1 (4) | C26—C25—C21 | 122.2 (5) |
C12—C11—C15 | 119.9 (4) | C25—C26—C27 | 119.9 (6) |
C11—C12—C13 | 121.2 (4) | C25—C26—H26 | 120.1 |
C11—C12—C14 | 120.4 (4) | C27—C26—H26 | 120.1 |
C13—C12—C14 | 117.7 (4) | C28—C27—C26 | 120.8 (7) |
O12—C13—C12 | 127.2 (4) | C28—C27—H27 | 119.6 |
O12—C13—C111 | 114.5 (4) | C26—C27—H27 | 119.6 |
C12—C13—C111 | 118.3 (4) | C29—C28—C27 | 119.4 (7) |
C117—C14—C12 | 114.5 (4) | C29—C28—H28 | 120.3 |
C117—C14—H14A | 108.6 | C27—C28—H28 | 120.3 |
C12—C14—H14A | 108.6 | C28—C29—C210 | 120.6 (7) |
C117—C14—H14B | 108.6 | C28—C29—H29 | 119.7 |
C12—C14—H14B | 108.6 | C210—C29—H29 | 119.7 |
H14A—C14—H14B | 107.6 | C25—C210—C29 | 120.8 (6) |
C110—C15—C16 | 118.5 (5) | C25—C210—H210 | 119.6 |
C110—C15—C11 | 118.2 (5) | C29—C210—H210 | 119.6 |
C16—C15—C11 | 123.3 (5) | C212—C211—C216 | 118.3 (5) |
C15—C16—C17 | 120.4 (6) | C212—C211—C23 | 119.9 (5) |
C15—C16—H16 | 119.8 | C216—C211—C23 | 121.6 (5) |
C17—C16—H16 | 119.8 | C211—C212—C213 | 120.0 (5) |
C18—C17—C16 | 121.3 (6) | C211—C212—H212 | 120.0 |
C18—C17—H17 | 119.3 | C213—C212—H212 | 120.0 |
C16—C17—H17 | 119.3 | C214—C213—C212 | 121.7 (6) |
C17—C18—C19 | 119.1 (6) | C214—C213—H213 | 119.2 |
C17—C18—H18 | 120.5 | C212—C213—H213 | 119.2 |
C19—C18—H18 | 120.5 | C213—C214—C215 | 119.0 (7) |
C18—C19—C110 | 119.8 (6) | C213—C214—H214 | 120.5 |
C18—C19—H19 | 120.1 | C215—C214—H214 | 120.5 |
C110—C19—H19 | 120.1 | C214—C215—C216 | 121.2 (6) |
C15—C110—C19 | 120.9 (5) | C214—C215—H215 | 119.4 |
C15—C110—H110 | 119.5 | C216—C215—H215 | 119.4 |
C19—C110—H110 | 119.5 | C215—C216—C211 | 119.8 (6) |
C112—C111—C116 | 117.5 (5) | C215—C216—H216 | 120.1 |
C112—C111—C13 | 120.1 (5) | C211—C216—H216 | 120.1 |
C116—C111—C13 | 122.2 (5) | C222—C217—C218 | 115.8 (6) |
C111—C112—C113 | 121.1 (5) | C222—C217—C24 | 122.4 (5) |
C111—C112—H112 | 119.5 | C218—C217—C24 | 121.8 (5) |
C113—C112—H112 | 119.5 | C219—C218—C217 | 123.2 (6) |
C114—C113—C112 | 120.7 (6) | C219—C218—H218 | 118.4 |
C114—C113—H113 | 119.7 | C217—C218—H218 | 118.4 |
C112—C113—H113 | 119.7 | C220—C219—C218 | 119.0 (6) |
C115—C114—C113 | 119.2 (6) | C220—C219—H219 | 120.5 |
C115—C114—H114 | 120.4 | C218—C219—H219 | 120.5 |
C113—C114—H114 | 120.4 | C221—C220—C219 | 119.2 (7) |
C114—C115—C116 | 120.3 (6) | C221—C220—H220 | 120.4 |
C114—C115—H115 | 119.9 | C219—C220—H220 | 120.4 |
C116—C115—H115 | 119.9 | C220—C221—C222 | 121.8 (6) |
C115—C116—C111 | 121.1 (6) | C220—C221—H221 | 119.1 |
C115—C116—H116 | 119.5 | C222—C221—H221 | 119.1 |
C111—C116—H116 | 119.5 | C217—C222—C221 | 120.9 (6) |
C127—C117—C123 | 124.1 (6) | C217—C222—H222 | 119.6 |
C127—C117—C118 | 99.9 (6) | C221—C222—H222 | 119.6 |
C123—C117—C122 | 129.0 (6) | C32—N31—C31 | 117.0 (5) |
C118—C117—C122 | 113.8 (5) | C32—N31—Ni | 122.7 (4) |
C127—C117—C14 | 126.1 (6) | C31—N31—Ni | 119.8 (4) |
C123—C117—C14 | 109.5 (5) | N31—C31—C35 | 123.0 (6) |
C118—C117—C14 | 130.5 (6) | N31—C31—H31 | 118.5 |
C122—C117—C14 | 115.4 (5) | C35—C31—H31 | 118.5 |
C119—C118—C117 | 124.0 (6) | N31—C32—C33 | 123.1 (6) |
C119—C118—H118 | 118.0 | N31—C32—H32 | 118.4 |
C117—C118—H118 | 118.0 | C33—C32—H32 | 118.4 |
C118—C119—C120 | 121.5 (6) | C34—C33—C32 | 118.9 (6) |
C118—C119—H119 | 119.2 | C34—C33—H33 | 120.5 |
C120—C119—H119 | 119.2 | C32—C33—H33 | 120.5 |
C119—C120—C121 | 117.0 (6) | C35—C34—C33 | 118.5 (6) |
C119—C120—H120 | 121.5 | C35—C34—H34 | 120.7 |
C121—C120—H120 | 121.5 | C33—C34—H34 | 120.7 |
C122—C121—C120 | 121.1 (6) | C34—C35—C31 | 119.5 (6) |
C122—C121—H121 | 119.5 | C34—C35—H35 | 120.2 |
C120—C121—H121 | 119.5 | C31—C35—H35 | 120.2 |
C121—C122—C117 | 122.2 (6) | C41—N41—C45 | 116.8 (5) |
C121—C122—H122 | 118.9 | C41—N41—Ni | 120.1 (4) |
C117—C122—H122 | 118.9 | C45—N41—Ni | 123.1 (4) |
C117—C123—C124 | 116.0 (6) | N41—C41—C42 | 124.5 (5) |
C117—C123—H123 | 122.0 | N41—C41—H41 | 117.7 |
C124—C123—H123 | 122.0 | C42—C41—H41 | 117.7 |
C125—C124—C123 | 120.5 (6) | C43—C42—C41 | 118.4 (5) |
C125—C124—H124 | 119.7 | C43—C42—H42 | 120.8 |
C123—C124—H124 | 119.7 | C41—C42—H42 | 120.8 |
C124—C125—C126 | 121.2 (7) | C42—C43—C44 | 118.6 (6) |
C124—C125—H125 | 119.4 | C42—C43—H43 | 120.7 |
C126—C125—H125 | 119.4 | C44—C43—H43 | 120.7 |
C125—C126—C127 | 118.1 (6) | C43—C44—C45 | 119.7 (6) |
C125—C126—H126 | 121.0 | C43—C44—H44 | 120.1 |
C127—C126—H126 | 121.0 | C45—C44—H44 | 120.1 |
C117—C127—C126 | 119.5 (7) | N41—C45—C44 | 121.9 (5) |
C117—C127—H127 | 120.3 | N41—C45—H45 | 119.0 |
C126—C127—H127 | 120.3 | C44—C45—H45 | 119.0 |
C21—O21—Ni | 128.0 (3) | ||
O22—Ni—O11—C11 | −161.8 (4) | N31—Ni—O22—C23 | 105.4 (4) |
O12—Ni—O11—C11 | 18.3 (4) | Ni—O21—C21—C22 | −0.9 (7) |
N41—Ni—O11—C11 | 109.9 (4) | Ni—O21—C21—C25 | 177.5 (3) |
N31—Ni—O11—C11 | −72.2 (4) | O21—C21—C22—C23 | 13.5 (8) |
O21—Ni—O12—C13 | 157.8 (4) | C25—C21—C22—C23 | −164.7 (4) |
O11—Ni—O12—C13 | −21.5 (4) | O21—C21—C22—C24 | −159.4 (4) |
N41—Ni—O12—C13 | −110.2 (4) | C25—C21—C22—C24 | 22.4 (7) |
N31—Ni—O12—C13 | 69.5 (4) | Ni—O22—C23—C22 | −11.4 (7) |
Ni—O11—C11—C12 | −6.9 (7) | Ni—O22—C23—C211 | 170.2 (3) |
Ni—O11—C11—C15 | 173.7 (3) | C21—C22—C23—O22 | −6.7 (8) |
O11—C11—C12—C13 | −9.9 (8) | C24—C22—C23—O22 | 166.2 (4) |
C15—C11—C12—C13 | 169.5 (4) | C21—C22—C23—C211 | 171.6 (4) |
O11—C11—C12—C14 | 160.2 (5) | C24—C22—C23—C211 | −15.5 (7) |
C15—C11—C12—C14 | −20.4 (7) | C21—C22—C24—C217 | 106.4 (5) |
Ni—O12—C13—C12 | 13.8 (7) | C23—C22—C24—C217 | −66.7 (6) |
Ni—O12—C13—C111 | −166.8 (3) | O21—C21—C25—C210 | 41.6 (6) |
C11—C12—C13—O12 | 6.2 (8) | C22—C21—C25—C210 | −140.0 (5) |
C14—C12—C13—O12 | −164.3 (4) | O21—C21—C25—C26 | −129.9 (5) |
C11—C12—C13—C111 | −173.2 (4) | C22—C21—C25—C26 | 48.5 (7) |
C14—C12—C13—C111 | 16.4 (6) | C210—C25—C26—C27 | 2.1 (8) |
C11—C12—C14—C117 | −103.7 (5) | C21—C25—C26—C27 | 173.7 (5) |
C13—C12—C14—C117 | 66.8 (6) | C25—C26—C27—C28 | −0.3 (10) |
O11—C11—C15—C110 | −49.9 (6) | C26—C27—C28—C29 | −1.7 (12) |
C12—C11—C15—C110 | 130.6 (5) | C27—C28—C29—C210 | 1.9 (12) |
O11—C11—C15—C16 | 128.4 (5) | C26—C25—C210—C29 | −1.9 (8) |
C12—C11—C15—C16 | −51.1 (7) | C21—C25—C210—C29 | −173.8 (5) |
C110—C15—C16—C17 | −1.5 (9) | C28—C29—C210—C25 | −0.1 (10) |
C11—C15—C16—C17 | −179.8 (5) | O22—C23—C211—C212 | −56.5 (6) |
C15—C16—C17—C18 | 0.3 (10) | C22—C23—C211—C212 | 124.9 (5) |
C16—C17—C18—C19 | 0.4 (11) | O22—C23—C211—C216 | 118.0 (5) |
C17—C18—C19—C110 | 0.0 (11) | C22—C23—C211—C216 | −60.6 (7) |
C16—C15—C110—C19 | 2.0 (9) | C216—C211—C212—C213 | 1.0 (8) |
C11—C15—C110—C19 | −179.7 (5) | C23—C211—C212—C213 | 175.6 (5) |
C18—C19—C110—C15 | −1.2 (10) | C211—C212—C213—C214 | 0.2 (9) |
O12—C13—C111—C112 | 63.4 (6) | C212—C213—C214—C215 | −2.6 (10) |
C12—C13—C111—C112 | −117.2 (5) | C213—C214—C215—C216 | 3.7 (11) |
O12—C13—C111—C116 | −111.8 (5) | C214—C215—C216—C211 | −2.5 (10) |
C12—C13—C111—C116 | 67.6 (6) | C212—C211—C216—C215 | 0.2 (8) |
C116—C111—C112—C113 | −3.2 (8) | C23—C211—C216—C215 | −174.4 (5) |
C13—C111—C112—C113 | −178.7 (5) | C22—C24—C217—C222 | −30.3 (8) |
C111—C112—C113—C114 | 1.7 (9) | C22—C24—C217—C218 | 151.3 (5) |
C112—C113—C114—C115 | 1.4 (10) | C222—C217—C218—C219 | −2.3 (9) |
C113—C114—C115—C116 | −2.9 (10) | C24—C217—C218—C219 | 176.2 (6) |
C114—C115—C116—C111 | 1.3 (9) | C217—C218—C219—C220 | 2.0 (11) |
C112—C111—C116—C115 | 1.8 (8) | C218—C219—C220—C221 | −1.9 (11) |
C13—C111—C116—C115 | 177.1 (5) | C219—C220—C221—C222 | 2.2 (12) |
C12—C14—C117—C127 | 31.6 (10) | C218—C217—C222—C221 | 2.6 (9) |
C12—C14—C117—C123 | −154.2 (5) | C24—C217—C222—C221 | −175.9 (6) |
C12—C14—C117—C118 | −123.0 (7) | C220—C221—C222—C217 | −2.7 (12) |
C12—C14—C117—C122 | 50.6 (8) | O21—Ni—N31—C32 | 142.0 (4) |
C127—C117—C118—C119 | 19.6 (10) | O22—Ni—N31—C32 | 53.5 (4) |
C123—C117—C118—C119 | −119.9 (13) | O12—Ni—N31—C32 | −128.7 (4) |
C122—C117—C118—C119 | 5.3 (11) | O11—Ni—N31—C32 | −40.7 (4) |
C14—C117—C118—C119 | 178.9 (7) | O21—Ni—N31—C31 | −28.8 (3) |
C117—C118—C119—C120 | −0.2 (13) | O22—Ni—N31—C31 | −117.3 (3) |
C118—C119—C120—C121 | −2.6 (14) | O12—Ni—N31—C31 | 60.5 (3) |
C119—C120—C121—C122 | −0.2 (16) | O11—Ni—N31—C31 | 148.5 (3) |
C120—C121—C122—C117 | 5.7 (16) | C32—N31—C31—C35 | −0.1 (7) |
C127—C117—C122—C121 | −54.8 (18) | Ni—N31—C31—C35 | 171.2 (4) |
C123—C117—C122—C121 | 28.0 (15) | C31—N31—C32—C33 | −0.8 (7) |
C118—C117—C122—C121 | −8.0 (13) | Ni—N31—C32—C33 | −171.8 (4) |
C14—C117—C122—C121 | 177.4 (8) | N31—C32—C33—C34 | 1.7 (9) |
C127—C117—C123—C124 | −4.2 (12) | C32—C33—C34—C35 | −1.6 (9) |
C118—C117—C123—C124 | 46.4 (9) | C33—C34—C35—C31 | 0.9 (9) |
C122—C117—C123—C124 | −27.7 (12) | N31—C31—C35—C34 | 0.0 (9) |
C14—C117—C123—C124 | −178.5 (7) | O21—Ni—N41—C41 | −145.9 (4) |
C117—C123—C124—C125 | −2.7 (13) | O22—Ni—N41—C41 | −57.5 (4) |
C123—C124—C125—C126 | 5.9 (18) | O12—Ni—N41—C41 | 124.7 (4) |
C124—C125—C126—C127 | −2.5 (18) | O11—Ni—N41—C41 | 36.7 (4) |
C123—C117—C127—C126 | 7.7 (16) | O21—Ni—N41—C45 | 36.9 (4) |
C118—C117—C127—C126 | −18.3 (13) | O22—Ni—N41—C45 | 125.3 (4) |
C122—C117—C127—C126 | 119 (3) | O12—Ni—N41—C45 | −52.5 (4) |
C14—C117—C127—C126 | −179.0 (8) | O11—Ni—N41—C45 | −140.5 (4) |
C125—C126—C127—C117 | −4.2 (17) | C45—N41—C41—C42 | 1.2 (7) |
O22—Ni—O21—C21 | −11.4 (4) | Ni—N41—C41—C42 | −176.1 (4) |
O12—Ni—O21—C21 | 168.5 (4) | N41—C41—C42—C43 | −0.6 (8) |
N41—Ni—O21—C21 | 76.9 (4) | C41—C42—C43—C44 | −0.4 (8) |
N31—Ni—O21—C21 | −101.0 (4) | C42—C43—C44—C45 | 0.6 (8) |
O21—Ni—O22—C23 | 17.1 (4) | C41—N41—C45—C44 | −0.9 (7) |
O11—Ni—O22—C23 | −163.6 (4) | Ni—N41—C45—C44 | 176.4 (4) |
N41—Ni—O22—C23 | −74.9 (4) | C43—C44—C45—N41 | 0.0 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C34—H34···O12i | 0.93 | 2.86 | 3.488 (7) | 126 |
C35—H35···O12i | 0.93 | 2.94 | 3.524 (6) | 123 |
C42—H42···O22ii | 0.93 | 3.14 | 3.652 (6) | 117 |
C43—H43···O22ii | 0.93 | 2.83 | 3.500 (6) | 130 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C22H17O2)2(C5H5N)2] |
Mr | 843.60 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 295 |
a, b, c (Å) | 10.8449 (11), 15.2308 (16), 26.770 (2) |
β (°) | 97.900 (8) |
V (Å3) | 4379.8 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.49 |
Crystal size (mm) | 0.2 × 0.1 × 0.1 |
Data collection | |
Diffractometer | Philips PW1100 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.879, 0.946 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9686, 9483, 3236 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.070, 0.159, 0.95 |
No. of reflections | 9483 |
No. of parameters | 596 |
No. of restraints | 18 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.35 |
Computer programs: STADI4 (Stoe & Cie, 1995), STADI4, X-RED (Stoe & Cie, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) Mercury (Version 1.2.1; Bruno et al., 2002) RasTop (Valadon, 2004) and POVRay (Version 3.6; Persistence of Vision, 2004), WinGX (Farrugia, 1999).
Ni—O11 | 2.033 (3) | Ni—O22 | 2.021 (3) |
Ni—O12 | 2.023 (3) | Ni—N31 | 2.131 (4) |
Ni—O21 | 2.003 (3) | Ni—N41 | 2.103 (4) |
O11—Ni—O12 | 88.01 (12) | O12—Ni—N41 | 91.58 (14) |
O11—Ni—O21 | 177.25 (13) | O21—Ni—O22 | 88.47 (12) |
O11—Ni—O22 | 94.19 (12) | O21—Ni—N31 | 88.30 (14) |
O11—Ni—N31 | 91.01 (14) | O21—Ni—N41 | 92.00 (14) |
O11—Ni—N41 | 88.79 (14) | O22—Ni—N31 | 89.55 (14) |
O12—Ni—O21 | 89.34 (12) | O22—Ni—N41 | 88.39 (13) |
O12—Ni—O22 | 177.80 (12) | N31—Ni—N41 | 177.91 (16) |
O12—Ni—N31 | 90.49 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C34—H34···O12i | 0.93 | 2.86 | 3.488 (7) | 126 |
C35—H35···O12i | 0.93 | 2.94 | 3.524 (6) | 123 |
C42—H42···O22ii | 0.93 | 3.14 | 3.652 (6) | 117 |
C43—H43···O22ii | 0.93 | 2.83 | 3.500 (6) | 130 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2. |
Coordination complexes of bivalent transition metal ions with β-diketonate ligands have proven useful in a wide range of applications (Soldatov et al., 2003). Notably, the ability to bind additional ligands to the monomeric complexes forms the basis for their often observed catalytic ability (Parkanyl et al., 1981). In this context, modification of the steric properties of the β-diketonato ligand is significant as a means of controlling the ability for additional ligand binding. With that in mind, we have prepared and structurally characterized the bis(pyridine) adduct of a NiII complex with a sterically demanding ligand, 2-benzyl-1,3-diphenylpropane-1,3-dione, α(Bzl)dbm.
The coordination sphere of the NiII centre (Fig. 1) is distorted octahedral, with the O donor atoms of the β-diketonate ligand occupying equatorial positions and N atoms of two pyridine ligands in the axial positions. The metal-to-ligand bond distances (Table 1) are in a good agreement with analogous values found in corresponding NiII β-diketonato complexes (Allen et al., 1983).
The benzyl groups of both ligands in the molecule are twisted out of the plane of the respective β-diketone fragment and establish C—H···π contacts involving the aromatic ring H atoms of the benzyl group and the π-systems of the pyridine ligands. The chelate ring planes, i.e. involving atoms O11, O12 and C11–C13 as well as O21, O22 and C21—C23, are tilted with respect to the central metal coordination plane involving atoms Ni, O11, O12, O21 and O22, forming angles of 17.8 (1) and 13.3 (1)°, respectively. The observed tilting may be partially explained by the action of C—H···π interactions with neighbouring complexes, which also result in short C···C contacts [C35···C45i = 3.463 (8) Å and C42···C216ii = 3.391 (7) Å; symmetry codes (i) −x, 1/2 + y, 1/2 − z; (ii) 1 − x, −1/2 + y, 1/2 − z]. In addition, the bending could also be partially stabilized by the aforementioned intramolecular C—H···π interactions involving the benzyl groups and coordinated pyridine ligands.
The torsion angles involving atoms of carbonyl groups and corresponding terminal phenyl groups are significantly larger [−50.0 (6), 63.0 (6), 42.0 (6) and −56.5 (6)°] than that found in the free ligand [19.56 (17) and 26.97 (8)°; Judaš & Kaitner, 2005]. Such distortion may be due to coordination to Ni, which enforces coplanarity of the chelate ring atoms, whereas in the free ligand each terminal phenyl group achieves maximum possible coplanarity with the neighbouring carbonyl system, with twisting occurring around the Cα atom of the molecule.
An analysis of the crystal packing indicated four C—H···O interactions between neighbouring complex molecules (two cooperative pairs, Table 2) involving the pyridine ring H atoms and β-diketonate O atoms. These contacts lead to the formation of layers (Fig. 2). The layers thus formed interact by way of C—H···π contacts [C28···C121iii = 3.61 (2) Å; symmetr code: (iii) x, 1/2 − y, 1/2 + z] between phenyl and benzyl groups from adjacent layers (Fig. 4).