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The nickel(II) complex trans-bis­(2-benzyl-1,3-diphenyl­propane-1,3-dionato)dipyridine­nickel(II), [Ni(C22H17O2)2(C5H5N)2], with a bulky β-diketonate ligand, 2-benzyl-1,3-di­phenyl­propane-1,3-dione, has an octa­hedral nickel(II) centre. Mol­ecules are held together by C—H...O and C—H...π inter­actions to form layers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040043/tk6292sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040043/tk6292Isup2.hkl
Contains datablock I

CCDC reference: 296684

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.009 Å
  • Disorder in main residue
  • R factor = 0.070
  • wR factor = 0.159
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 34 Perc. PLAT480_ALERT_4_B Long H...A H-Bond Reported H42 .. O22 .. 3.14 Ang.
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.67 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C19 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C218 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C221 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C217 PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C217 -C222 1.36 Ang. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT480_ALERT_4_C Long H...A H-Bond Reported H34 .. O12 .. 2.86 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H35 .. O12 .. 2.94 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H43 .. O22 .. 2.83 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

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).

Experimental top

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.

Refinement top

The H atoms were included in the riding-model approximation with C—H(aromatic) = 0.93 Å, CH(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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. View of the title complex, showing the atomic numbering. Displacement ellipsoids are drawn at the 30% probability level. For clarity, only the major component of the disordered aromatic ring is shown.
[Figure 2] Fig. 2. Crystal packing diagram showing four C—H···O interactions (dashed lines) between neighbouring complex molecules that lead to the formation of layers.
[Figure 3] Fig. 3. Crystal packing diagram showing C—H···π interactions (dashed lines) between phenyl and benzyl groups of complex molecules derived from adjacent layers.
trans-bis(2-benzyl-1,3-diphenylpropane-1,3-dionato)dipyridinenickel(II) top
Crystal data top
[Ni(C22H17O2)2(C5H5N)2]F(000) = 1768
Mr = 843.60Dx = 1.279 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 36 reflections
a = 10.8449 (11) Åθ = 10.0–13.6°
b = 15.2308 (16) ŵ = 0.49 mm1
c = 26.770 (2) ÅT = 295 K
β = 97.900 (8)°Prism, yellow
V = 4379.8 (7) Å30.2 × 0.1 × 0.1 mm
Z = 4
Data collection top
Philips PW1100
diffractometer
3236 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
Planar Graphite monochromatorθmax = 27.0°, θmin = 2.0°
ω scansh = 1313
Absorption correction: ψ scan
(North et al., 1968)
k = 019
Tmin = 0.879, Tmax = 0.946l = 034
9686 measured reflections3 standard reflections every 60 min
9483 independent reflections intensity decay: 6.5%
Refinement top
Refinement on F218 restraints
Least-squares matrix: fullH-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 = 0.95Δρmax = 0.37 e Å3
9483 reflectionsΔρmin = 0.35 e Å3
596 parameters
Crystal data top
[Ni(C22H17O2)2(C5H5N)2]V = 4379.8 (7) Å3
Mr = 843.60Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.8449 (11) ŵ = 0.49 mm1
b = 15.2308 (16) ÅT = 295 K
c = 26.770 (2) Å0.2 × 0.1 × 0.1 mm
β = 97.900 (8)°
Data collection top
Philips PW1100
diffractometer
3236 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.062
Tmin = 0.879, Tmax = 0.9463 standard reflections every 60 min
9686 measured reflections intensity decay: 6.5%
9483 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07018 restraints
wR(F2) = 0.159H-atom parameters constrained
S = 0.95Δρmax = 0.37 e Å3
9483 reflectionsΔρmin = 0.35 e Å3
596 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ni0.24253 (6)0.11351 (4)0.24548 (2)0.0444 (2)
O110.2924 (3)0.1020 (2)0.17527 (10)0.0497 (9)
O120.0747 (3)0.0630 (2)0.21752 (11)0.0505 (9)
C110.2193 (5)0.0931 (3)0.13454 (17)0.0465 (13)
C120.0892 (5)0.0805 (3)0.12920 (16)0.0484 (13)
C130.0275 (4)0.0627 (3)0.17172 (18)0.0469 (12)
C140.0079 (5)0.1002 (3)0.07858 (16)0.0643 (16)
H14A0.06110.10230.05230.077*
H14B0.05030.05220.07080.077*
C150.2849 (5)0.0963 (3)0.08844 (17)0.0513 (13)
C160.2705 (6)0.0335 (4)0.05157 (19)0.0755 (18)
H160.21790.01400.05430.091*
C170.3336 (7)0.0401 (4)0.0104 (2)0.091 (2)
H170.32250.00300.01440.109*
C180.4116 (6)0.1084 (5)0.0053 (2)0.093 (2)
H180.45310.11230.02280.112*
C190.4280 (6)0.1708 (5)0.0419 (2)0.100 (2)
H190.48110.21790.03900.119*
C1100.3647 (5)0.1639 (4)0.0840 (2)0.0743 (17)
H1100.37750.20620.10930.089*
C1110.1096 (5)0.0398 (3)0.16265 (17)0.0488 (13)
C1120.1952 (5)0.0934 (4)0.1810 (2)0.0652 (15)
H1120.16830.14430.19830.078*
C1130.3197 (6)0.0729 (5)0.1741 (2)0.0825 (18)
H1130.37630.11080.18600.099*
C1140.3615 (6)0.0029 (5)0.1498 (2)0.085 (2)
H1140.44610.01590.14460.102*
C1150.2778 (6)0.0590 (5)0.1335 (2)0.089 (2)
H1150.30490.11180.11840.107*
C1160.1529 (5)0.0377 (4)0.13934 (19)0.0698 (16)
H1160.09680.07600.12740.084*
C1170.0644 (5)0.1849 (3)0.07766 (19)0.0748 (10)
C1180.1911 (7)0.2005 (6)0.0670 (3)0.0748 (10)0.53
H1180.24330.15290.05840.090*0.53
C1190.2431 (7)0.2804 (6)0.0684 (4)0.0748 (10)0.53
H1190.32900.28600.06070.090*0.53
C1200.1721 (8)0.3542 (5)0.0811 (4)0.0748 (10)0.53
H1200.20770.40980.08080.090*0.53
C1210.0452 (8)0.3419 (5)0.0943 (4)0.0748 (10)0.53
H1210.00570.39020.10290.090*0.53
C1220.0062 (7)0.2601 (5)0.0947 (4)0.0748 (10)0.53
H1220.09030.25340.10660.090*0.53
C1230.1702 (8)0.1791 (6)0.0417 (3)0.0748 (10)0.47
H1230.18960.12850.02290.090*0.47
C1240.2440 (8)0.2529 (6)0.0359 (4)0.0748 (10)0.47
H1240.31390.25370.01150.090*0.47
C1250.2157 (10)0.3246 (7)0.0654 (4)0.0748 (10)0.47
H1250.27060.37180.06310.090*0.47
C1260.1068 (9)0.3288 (6)0.0989 (4)0.0748 (10)0.47
H1260.08620.37880.11810.090*0.47
C1270.0293 (8)0.2563 (6)0.1029 (4)0.0748 (10)0.47
H1270.04720.25830.12340.090*0.47
O210.1849 (3)0.1241 (2)0.31317 (11)0.0505 (9)
O220.4081 (3)0.1641 (2)0.27606 (11)0.0471 (8)
C210.2495 (5)0.1405 (3)0.35508 (17)0.0459 (13)
C220.3795 (5)0.1543 (3)0.36358 (17)0.0502 (13)
C230.4489 (4)0.1691 (3)0.32305 (18)0.0449 (12)
C240.4499 (5)0.1429 (3)0.41652 (17)0.0628 (15)
H24A0.50350.19340.42440.075*
H24B0.39010.14210.44040.075*
C250.1716 (5)0.1472 (4)0.39754 (17)0.0519 (13)
C260.1813 (5)0.2172 (4)0.43050 (19)0.0704 (16)
H260.24270.25940.42910.085*
C270.0996 (7)0.2245 (6)0.4657 (2)0.105 (3)
H270.10670.27170.48790.126*
C280.0087 (7)0.1634 (7)0.4681 (3)0.116 (3)
H280.04440.16800.49240.139*
C290.0034 (6)0.0967 (5)0.4351 (2)0.107 (2)
H290.06680.05590.43600.128*
C2100.0778 (5)0.0880 (4)0.3997 (2)0.0748 (17)
H2100.06830.04130.37710.090*
C2110.5832 (5)0.1958 (3)0.33378 (17)0.0502 (13)
C2120.6726 (5)0.1474 (4)0.31432 (19)0.0613 (15)
H2120.65060.09610.29650.074*
C2130.7954 (6)0.1752 (5)0.3213 (2)0.0832 (19)
H2130.85490.14210.30790.100*
C2140.8308 (7)0.2492 (5)0.3472 (3)0.099 (2)
H2140.91410.26570.35270.118*
C2150.7432 (7)0.2990 (5)0.3649 (2)0.096 (2)
H2150.76630.35180.38100.115*
C2160.6195 (5)0.2729 (4)0.3596 (2)0.0760 (18)
H2160.56100.30680.37320.091*
C2170.5285 (5)0.0606 (4)0.42393 (18)0.0562 (14)
C2180.6343 (6)0.0567 (5)0.4586 (2)0.094 (2)
H2180.66020.10740.47640.113*
C2190.7037 (6)0.0184 (5)0.4682 (2)0.097 (2)
H2190.77330.01870.49270.116*
C2200.6694 (7)0.0913 (5)0.4418 (3)0.098 (2)
H2200.71640.14240.44700.117*
C2210.5668 (8)0.0897 (5)0.4077 (3)0.120 (3)
H2210.54160.14090.39030.144*
C2220.4976 (6)0.0144 (4)0.3978 (2)0.090 (2)
H2220.42880.01500.37290.108*
N310.1748 (4)0.2431 (3)0.22909 (15)0.0484 (11)
C310.0786 (5)0.2734 (4)0.25069 (19)0.0631 (15)
H310.03590.23440.26880.076*
C320.2335 (5)0.3004 (4)0.2035 (2)0.0635 (15)
H320.30110.28100.18860.076*
C330.1991 (6)0.3875 (4)0.1980 (2)0.0836 (19)
H330.24140.42540.17900.100*
C340.1015 (7)0.4174 (4)0.2210 (2)0.082 (2)
H340.07770.47600.21860.098*
C350.0405 (6)0.3593 (4)0.2472 (2)0.081 (2)
H350.02670.37770.26280.097*
N410.3159 (4)0.0125 (3)0.26235 (14)0.0473 (10)
C410.4177 (5)0.0381 (4)0.24427 (18)0.0586 (14)
H410.45730.00250.22600.070*
C420.4687 (5)0.1202 (4)0.2507 (2)0.0688 (16)
H420.54010.13470.23680.083*
C430.4127 (6)0.1797 (4)0.2776 (2)0.0717 (17)
H430.44460.23630.28260.086*
C440.3091 (6)0.1553 (4)0.2973 (2)0.0732 (17)
H440.26950.19490.31630.088*
C450.2623 (5)0.0707 (4)0.28908 (18)0.0577 (14)
H450.19130.05460.30280.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni0.0493 (4)0.0469 (4)0.0372 (3)0.0008 (3)0.0067 (3)0.0029 (3)
O110.056 (2)0.054 (2)0.0389 (18)0.0026 (18)0.0072 (16)0.0008 (17)
O120.053 (2)0.061 (2)0.0360 (18)0.0072 (18)0.0018 (16)0.0010 (16)
C110.069 (4)0.035 (3)0.037 (3)0.003 (3)0.009 (3)0.004 (2)
C120.061 (4)0.047 (3)0.036 (3)0.008 (3)0.006 (3)0.001 (2)
C130.053 (3)0.035 (3)0.051 (3)0.004 (3)0.001 (3)0.002 (2)
C140.075 (4)0.076 (4)0.041 (3)0.023 (3)0.004 (3)0.004 (3)
C150.058 (3)0.054 (4)0.042 (3)0.004 (3)0.008 (2)0.002 (3)
C160.117 (5)0.060 (4)0.057 (3)0.007 (4)0.038 (3)0.015 (3)
C170.135 (6)0.076 (5)0.069 (4)0.003 (5)0.044 (4)0.027 (4)
C180.103 (5)0.116 (6)0.067 (4)0.000 (5)0.038 (4)0.009 (5)
C190.105 (5)0.111 (6)0.090 (5)0.040 (5)0.040 (4)0.004 (5)
C1100.084 (4)0.080 (5)0.064 (4)0.022 (4)0.030 (3)0.013 (3)
C1110.057 (3)0.051 (3)0.037 (3)0.010 (3)0.000 (2)0.003 (3)
C1120.063 (4)0.058 (4)0.075 (4)0.012 (3)0.012 (3)0.009 (3)
C1130.069 (5)0.085 (5)0.098 (5)0.002 (4)0.024 (4)0.003 (4)
C1140.066 (4)0.112 (6)0.079 (4)0.023 (4)0.015 (4)0.013 (4)
C1150.081 (5)0.095 (5)0.092 (5)0.035 (4)0.015 (4)0.034 (4)
C1160.067 (4)0.071 (4)0.073 (4)0.012 (3)0.013 (3)0.020 (3)
C1170.063 (2)0.091 (3)0.070 (2)0.0053 (19)0.0030 (18)0.0143 (19)
C1180.063 (2)0.091 (3)0.070 (2)0.0053 (19)0.0030 (18)0.0143 (19)
C1190.063 (2)0.091 (3)0.070 (2)0.0053 (19)0.0030 (18)0.0143 (19)
C1200.063 (2)0.091 (3)0.070 (2)0.0053 (19)0.0030 (18)0.0143 (19)
C1210.063 (2)0.091 (3)0.070 (2)0.0053 (19)0.0030 (18)0.0143 (19)
C1220.063 (2)0.091 (3)0.070 (2)0.0053 (19)0.0030 (18)0.0143 (19)
C1230.063 (2)0.091 (3)0.070 (2)0.0053 (19)0.0030 (18)0.0143 (19)
C1240.063 (2)0.091 (3)0.070 (2)0.0053 (19)0.0030 (18)0.0143 (19)
C1250.063 (2)0.091 (3)0.070 (2)0.0053 (19)0.0030 (18)0.0143 (19)
C1260.063 (2)0.091 (3)0.070 (2)0.0053 (19)0.0030 (18)0.0143 (19)
C1270.063 (2)0.091 (3)0.070 (2)0.0053 (19)0.0030 (18)0.0143 (19)
O210.055 (2)0.061 (2)0.0363 (18)0.0028 (18)0.0077 (16)0.0032 (17)
O220.054 (2)0.051 (2)0.0357 (18)0.0030 (17)0.0020 (16)0.0020 (16)
C210.058 (3)0.043 (3)0.036 (3)0.005 (3)0.003 (3)0.002 (2)
C220.058 (4)0.053 (3)0.039 (3)0.001 (3)0.004 (3)0.003 (2)
C230.051 (3)0.037 (3)0.046 (3)0.006 (2)0.003 (3)0.001 (2)
C240.069 (4)0.070 (4)0.048 (3)0.003 (3)0.002 (3)0.011 (3)
C250.061 (4)0.059 (4)0.036 (3)0.012 (3)0.005 (3)0.003 (3)
C260.085 (4)0.071 (4)0.057 (4)0.010 (3)0.013 (3)0.007 (3)
C270.114 (6)0.141 (8)0.062 (4)0.036 (5)0.025 (4)0.030 (5)
C280.099 (6)0.192 (10)0.064 (5)0.021 (6)0.039 (5)0.004 (6)
C290.096 (5)0.159 (8)0.073 (5)0.017 (5)0.037 (4)0.002 (5)
C2100.077 (4)0.091 (5)0.061 (4)0.001 (4)0.026 (3)0.010 (3)
C2110.059 (4)0.046 (3)0.044 (3)0.001 (3)0.001 (3)0.001 (3)
C2120.055 (4)0.060 (4)0.068 (4)0.000 (3)0.006 (3)0.001 (3)
C2130.057 (4)0.107 (6)0.086 (5)0.011 (4)0.014 (3)0.003 (4)
C2140.070 (5)0.119 (7)0.101 (5)0.027 (5)0.008 (4)0.015 (5)
C2150.082 (5)0.098 (6)0.104 (5)0.026 (5)0.003 (4)0.034 (4)
C2160.065 (4)0.078 (5)0.083 (4)0.001 (4)0.005 (3)0.017 (4)
C2170.060 (4)0.070 (4)0.038 (3)0.004 (3)0.003 (3)0.004 (3)
C2180.100 (5)0.090 (5)0.081 (5)0.006 (4)0.031 (4)0.006 (4)
C2190.087 (5)0.091 (6)0.100 (5)0.008 (5)0.033 (4)0.021 (5)
C2200.107 (6)0.093 (6)0.086 (5)0.030 (5)0.012 (4)0.012 (4)
C2210.158 (7)0.070 (5)0.112 (6)0.016 (5)0.051 (5)0.009 (4)
C2220.104 (5)0.070 (5)0.084 (4)0.016 (4)0.035 (4)0.005 (4)
N310.048 (3)0.044 (3)0.052 (3)0.003 (2)0.001 (2)0.006 (2)
C310.064 (4)0.065 (4)0.059 (3)0.014 (3)0.005 (3)0.004 (3)
C320.053 (4)0.058 (4)0.079 (4)0.006 (3)0.008 (3)0.011 (3)
C330.096 (5)0.046 (4)0.106 (5)0.005 (4)0.004 (4)0.004 (4)
C340.106 (6)0.040 (4)0.094 (5)0.019 (4)0.008 (4)0.008 (4)
C350.088 (5)0.077 (5)0.075 (4)0.042 (4)0.002 (4)0.010 (4)
N410.048 (3)0.047 (3)0.046 (2)0.001 (2)0.004 (2)0.001 (2)
C410.055 (4)0.059 (4)0.064 (3)0.006 (3)0.017 (3)0.006 (3)
C420.073 (4)0.071 (5)0.064 (3)0.014 (4)0.017 (3)0.000 (4)
C430.086 (5)0.051 (4)0.076 (4)0.016 (4)0.005 (4)0.010 (3)
C440.101 (5)0.047 (4)0.072 (4)0.021 (4)0.013 (4)0.002 (3)
C450.060 (4)0.054 (4)0.061 (3)0.009 (3)0.014 (3)0.003 (3)
Geometric parameters (Å, º) top
Ni—O112.033 (3)C21—C251.509 (6)
Ni—O122.023 (3)C22—C231.421 (6)
Ni—O212.003 (3)C22—C241.525 (6)
Ni—O222.021 (3)C23—C2111.501 (6)
Ni—N312.131 (4)C24—C2171.512 (7)
Ni—N412.103 (4)C24—H24A0.9700
O11—C111.264 (5)C24—H24B0.9700
O12—C131.262 (5)C25—C2101.366 (7)
C11—C121.412 (6)C25—C261.379 (7)
C11—C151.508 (6)C26—C271.383 (7)
C12—C131.423 (6)C26—H260.9300
C12—C141.541 (6)C27—C281.363 (9)
C13—C1111.514 (6)C27—H270.9300
C14—C1171.508 (7)C28—C291.341 (9)
C14—H14A0.9700C28—H280.9300
C14—H14B0.9700C29—C2101.387 (7)
C15—C1101.361 (7)C29—H290.9300
C15—C161.368 (6)C210—H2100.9300
C16—C171.379 (7)C211—C2121.376 (6)
C16—H160.9300C211—C2161.391 (7)
C17—C181.359 (8)C212—C2131.385 (7)
C17—H170.9300C212—H2120.9300
C18—C191.357 (8)C213—C2141.350 (8)
C18—H180.9300C213—H2130.9300
C19—C1101.403 (7)C214—C2151.352 (8)
C19—H190.9300C214—H2140.9300
C110—H1100.9300C215—C2161.388 (7)
C111—C1121.377 (6)C215—H2150.9300
C111—C1161.386 (7)C216—H2160.9300
C112—C1131.373 (7)C217—C2221.358 (7)
C112—H1120.9300C217—C2181.374 (7)
C113—C1141.370 (8)C218—C2191.375 (8)
C113—H1130.9300C218—H2180.9300
C114—C1151.361 (8)C219—C2201.342 (8)
C114—H1140.9300C219—H2190.9300
C115—C1161.381 (7)C220—C2211.338 (8)
C115—H1150.9300C220—H2200.9300
C116—H1160.9300C221—C2221.376 (8)
C117—C1271.310 (7)C221—H2210.9300
C117—C1231.395 (7)C222—H2220.9300
C117—C1181.385 (7)N31—C321.325 (6)
C117—C1221.418 (7)N31—C311.342 (6)
C118—C1191.343 (7)C31—C351.371 (7)
C118—H1180.9300C31—H310.9300
C119—C1201.378 (7)C32—C331.381 (7)
C119—H1190.9300C32—H320.9300
C120—C1211.385 (7)C33—C341.373 (8)
C120—H1200.9300C33—H330.9300
C121—C1221.365 (7)C34—C351.357 (7)
C121—H1210.9300C34—H340.9300
C122—H1220.9300C35—H350.9300
C123—C1241.376 (8)N41—C411.324 (5)
C123—H1230.9300N41—C451.323 (6)
C124—C1251.359 (8)C41—C421.368 (6)
C124—H1240.9300C41—H410.9300
C125—C1261.382 (8)C42—C431.354 (7)
C125—H1250.9300C42—H420.9300
C126—C1271.382 (8)C43—C441.358 (7)
C126—H1260.9300C43—H430.9300
C127—H1270.9300C44—C451.391 (7)
O21—C211.263 (5)C44—H440.9300
O22—C231.277 (5)C45—H450.9300
C21—C221.413 (6)
O11—Ni—O1288.01 (12)C23—O22—Ni126.2 (3)
O11—Ni—O21177.25 (13)O21—C21—C22126.3 (4)
O11—Ni—O2294.19 (12)O21—C21—C25112.5 (4)
O11—Ni—N3191.01 (14)C22—C21—C25121.2 (4)
O11—Ni—N4188.79 (14)C21—C22—C23121.5 (4)
O12—Ni—O2189.34 (12)C21—C22—C24119.6 (4)
O12—Ni—O22177.80 (12)C23—C22—C24118.5 (5)
O12—Ni—N3190.49 (14)O22—C23—C22126.5 (4)
O12—Ni—N4191.58 (14)O22—C23—C211113.6 (4)
O21—Ni—O2288.47 (12)C22—C23—C211119.9 (4)
O21—Ni—N3188.30 (14)C217—C24—C22114.7 (4)
O21—Ni—N4192.00 (14)C217—C24—H24A108.6
O22—Ni—N3189.55 (14)C22—C24—H24A108.6
O22—Ni—N4188.39 (13)C217—C24—H24B108.6
N31—Ni—N41177.91 (16)C22—C24—H24B108.6
C11—O11—Ni126.3 (3)H24A—C24—H24B107.6
C13—O12—Ni125.8 (3)C210—C25—C26118.4 (5)
O11—C11—C12127.0 (4)C210—C25—C21118.9 (5)
O11—C11—C15113.1 (4)C26—C25—C21122.2 (5)
C12—C11—C15119.9 (4)C25—C26—C27119.9 (6)
C11—C12—C13121.2 (4)C25—C26—H26120.1
C11—C12—C14120.4 (4)C27—C26—H26120.1
C13—C12—C14117.7 (4)C28—C27—C26120.8 (7)
O12—C13—C12127.2 (4)C28—C27—H27119.6
O12—C13—C111114.5 (4)C26—C27—H27119.6
C12—C13—C111118.3 (4)C29—C28—C27119.4 (7)
C117—C14—C12114.5 (4)C29—C28—H28120.3
C117—C14—H14A108.6C27—C28—H28120.3
C12—C14—H14A108.6C28—C29—C210120.6 (7)
C117—C14—H14B108.6C28—C29—H29119.7
C12—C14—H14B108.6C210—C29—H29119.7
H14A—C14—H14B107.6C25—C210—C29120.8 (6)
C110—C15—C16118.5 (5)C25—C210—H210119.6
C110—C15—C11118.2 (5)C29—C210—H210119.6
C16—C15—C11123.3 (5)C212—C211—C216118.3 (5)
C15—C16—C17120.4 (6)C212—C211—C23119.9 (5)
C15—C16—H16119.8C216—C211—C23121.6 (5)
C17—C16—H16119.8C211—C212—C213120.0 (5)
C18—C17—C16121.3 (6)C211—C212—H212120.0
C18—C17—H17119.3C213—C212—H212120.0
C16—C17—H17119.3C214—C213—C212121.7 (6)
C17—C18—C19119.1 (6)C214—C213—H213119.2
C17—C18—H18120.5C212—C213—H213119.2
C19—C18—H18120.5C213—C214—C215119.0 (7)
C18—C19—C110119.8 (6)C213—C214—H214120.5
C18—C19—H19120.1C215—C214—H214120.5
C110—C19—H19120.1C214—C215—C216121.2 (6)
C15—C110—C19120.9 (5)C214—C215—H215119.4
C15—C110—H110119.5C216—C215—H215119.4
C19—C110—H110119.5C215—C216—C211119.8 (6)
C112—C111—C116117.5 (5)C215—C216—H216120.1
C112—C111—C13120.1 (5)C211—C216—H216120.1
C116—C111—C13122.2 (5)C222—C217—C218115.8 (6)
C111—C112—C113121.1 (5)C222—C217—C24122.4 (5)
C111—C112—H112119.5C218—C217—C24121.8 (5)
C113—C112—H112119.5C219—C218—C217123.2 (6)
C114—C113—C112120.7 (6)C219—C218—H218118.4
C114—C113—H113119.7C217—C218—H218118.4
C112—C113—H113119.7C220—C219—C218119.0 (6)
C115—C114—C113119.2 (6)C220—C219—H219120.5
C115—C114—H114120.4C218—C219—H219120.5
C113—C114—H114120.4C221—C220—C219119.2 (7)
C114—C115—C116120.3 (6)C221—C220—H220120.4
C114—C115—H115119.9C219—C220—H220120.4
C116—C115—H115119.9C220—C221—C222121.8 (6)
C115—C116—C111121.1 (6)C220—C221—H221119.1
C115—C116—H116119.5C222—C221—H221119.1
C111—C116—H116119.5C217—C222—C221120.9 (6)
C127—C117—C123124.1 (6)C217—C222—H222119.6
C127—C117—C11899.9 (6)C221—C222—H222119.6
C123—C117—C122129.0 (6)C32—N31—C31117.0 (5)
C118—C117—C122113.8 (5)C32—N31—Ni122.7 (4)
C127—C117—C14126.1 (6)C31—N31—Ni119.8 (4)
C123—C117—C14109.5 (5)N31—C31—C35123.0 (6)
C118—C117—C14130.5 (6)N31—C31—H31118.5
C122—C117—C14115.4 (5)C35—C31—H31118.5
C119—C118—C117124.0 (6)N31—C32—C33123.1 (6)
C119—C118—H118118.0N31—C32—H32118.4
C117—C118—H118118.0C33—C32—H32118.4
C118—C119—C120121.5 (6)C34—C33—C32118.9 (6)
C118—C119—H119119.2C34—C33—H33120.5
C120—C119—H119119.2C32—C33—H33120.5
C119—C120—C121117.0 (6)C35—C34—C33118.5 (6)
C119—C120—H120121.5C35—C34—H34120.7
C121—C120—H120121.5C33—C34—H34120.7
C122—C121—C120121.1 (6)C34—C35—C31119.5 (6)
C122—C121—H121119.5C34—C35—H35120.2
C120—C121—H121119.5C31—C35—H35120.2
C121—C122—C117122.2 (6)C41—N41—C45116.8 (5)
C121—C122—H122118.9C41—N41—Ni120.1 (4)
C117—C122—H122118.9C45—N41—Ni123.1 (4)
C117—C123—C124116.0 (6)N41—C41—C42124.5 (5)
C117—C123—H123122.0N41—C41—H41117.7
C124—C123—H123122.0C42—C41—H41117.7
C125—C124—C123120.5 (6)C43—C42—C41118.4 (5)
C125—C124—H124119.7C43—C42—H42120.8
C123—C124—H124119.7C41—C42—H42120.8
C124—C125—C126121.2 (7)C42—C43—C44118.6 (6)
C124—C125—H125119.4C42—C43—H43120.7
C126—C125—H125119.4C44—C43—H43120.7
C125—C126—C127118.1 (6)C43—C44—C45119.7 (6)
C125—C126—H126121.0C43—C44—H44120.1
C127—C126—H126121.0C45—C44—H44120.1
C117—C127—C126119.5 (7)N41—C45—C44121.9 (5)
C117—C127—H127120.3N41—C45—H45119.0
C126—C127—H127120.3C44—C45—H45119.0
C21—O21—Ni128.0 (3)
O22—Ni—O11—C11161.8 (4)N31—Ni—O22—C23105.4 (4)
O12—Ni—O11—C1118.3 (4)Ni—O21—C21—C220.9 (7)
N41—Ni—O11—C11109.9 (4)Ni—O21—C21—C25177.5 (3)
N31—Ni—O11—C1172.2 (4)O21—C21—C22—C2313.5 (8)
O21—Ni—O12—C13157.8 (4)C25—C21—C22—C23164.7 (4)
O11—Ni—O12—C1321.5 (4)O21—C21—C22—C24159.4 (4)
N41—Ni—O12—C13110.2 (4)C25—C21—C22—C2422.4 (7)
N31—Ni—O12—C1369.5 (4)Ni—O22—C23—C2211.4 (7)
Ni—O11—C11—C126.9 (7)Ni—O22—C23—C211170.2 (3)
Ni—O11—C11—C15173.7 (3)C21—C22—C23—O226.7 (8)
O11—C11—C12—C139.9 (8)C24—C22—C23—O22166.2 (4)
C15—C11—C12—C13169.5 (4)C21—C22—C23—C211171.6 (4)
O11—C11—C12—C14160.2 (5)C24—C22—C23—C21115.5 (7)
C15—C11—C12—C1420.4 (7)C21—C22—C24—C217106.4 (5)
Ni—O12—C13—C1213.8 (7)C23—C22—C24—C21766.7 (6)
Ni—O12—C13—C111166.8 (3)O21—C21—C25—C21041.6 (6)
C11—C12—C13—O126.2 (8)C22—C21—C25—C210140.0 (5)
C14—C12—C13—O12164.3 (4)O21—C21—C25—C26129.9 (5)
C11—C12—C13—C111173.2 (4)C22—C21—C25—C2648.5 (7)
C14—C12—C13—C11116.4 (6)C210—C25—C26—C272.1 (8)
C11—C12—C14—C117103.7 (5)C21—C25—C26—C27173.7 (5)
C13—C12—C14—C11766.8 (6)C25—C26—C27—C280.3 (10)
O11—C11—C15—C11049.9 (6)C26—C27—C28—C291.7 (12)
C12—C11—C15—C110130.6 (5)C27—C28—C29—C2101.9 (12)
O11—C11—C15—C16128.4 (5)C26—C25—C210—C291.9 (8)
C12—C11—C15—C1651.1 (7)C21—C25—C210—C29173.8 (5)
C110—C15—C16—C171.5 (9)C28—C29—C210—C250.1 (10)
C11—C15—C16—C17179.8 (5)O22—C23—C211—C21256.5 (6)
C15—C16—C17—C180.3 (10)C22—C23—C211—C212124.9 (5)
C16—C17—C18—C190.4 (11)O22—C23—C211—C216118.0 (5)
C17—C18—C19—C1100.0 (11)C22—C23—C211—C21660.6 (7)
C16—C15—C110—C192.0 (9)C216—C211—C212—C2131.0 (8)
C11—C15—C110—C19179.7 (5)C23—C211—C212—C213175.6 (5)
C18—C19—C110—C151.2 (10)C211—C212—C213—C2140.2 (9)
O12—C13—C111—C11263.4 (6)C212—C213—C214—C2152.6 (10)
C12—C13—C111—C112117.2 (5)C213—C214—C215—C2163.7 (11)
O12—C13—C111—C116111.8 (5)C214—C215—C216—C2112.5 (10)
C12—C13—C111—C11667.6 (6)C212—C211—C216—C2150.2 (8)
C116—C111—C112—C1133.2 (8)C23—C211—C216—C215174.4 (5)
C13—C111—C112—C113178.7 (5)C22—C24—C217—C22230.3 (8)
C111—C112—C113—C1141.7 (9)C22—C24—C217—C218151.3 (5)
C112—C113—C114—C1151.4 (10)C222—C217—C218—C2192.3 (9)
C113—C114—C115—C1162.9 (10)C24—C217—C218—C219176.2 (6)
C114—C115—C116—C1111.3 (9)C217—C218—C219—C2202.0 (11)
C112—C111—C116—C1151.8 (8)C218—C219—C220—C2211.9 (11)
C13—C111—C116—C115177.1 (5)C219—C220—C221—C2222.2 (12)
C12—C14—C117—C12731.6 (10)C218—C217—C222—C2212.6 (9)
C12—C14—C117—C123154.2 (5)C24—C217—C222—C221175.9 (6)
C12—C14—C117—C118123.0 (7)C220—C221—C222—C2172.7 (12)
C12—C14—C117—C12250.6 (8)O21—Ni—N31—C32142.0 (4)
C127—C117—C118—C11919.6 (10)O22—Ni—N31—C3253.5 (4)
C123—C117—C118—C119119.9 (13)O12—Ni—N31—C32128.7 (4)
C122—C117—C118—C1195.3 (11)O11—Ni—N31—C3240.7 (4)
C14—C117—C118—C119178.9 (7)O21—Ni—N31—C3128.8 (3)
C117—C118—C119—C1200.2 (13)O22—Ni—N31—C31117.3 (3)
C118—C119—C120—C1212.6 (14)O12—Ni—N31—C3160.5 (3)
C119—C120—C121—C1220.2 (16)O11—Ni—N31—C31148.5 (3)
C120—C121—C122—C1175.7 (16)C32—N31—C31—C350.1 (7)
C127—C117—C122—C12154.8 (18)Ni—N31—C31—C35171.2 (4)
C123—C117—C122—C12128.0 (15)C31—N31—C32—C330.8 (7)
C118—C117—C122—C1218.0 (13)Ni—N31—C32—C33171.8 (4)
C14—C117—C122—C121177.4 (8)N31—C32—C33—C341.7 (9)
C127—C117—C123—C1244.2 (12)C32—C33—C34—C351.6 (9)
C118—C117—C123—C12446.4 (9)C33—C34—C35—C310.9 (9)
C122—C117—C123—C12427.7 (12)N31—C31—C35—C340.0 (9)
C14—C117—C123—C124178.5 (7)O21—Ni—N41—C41145.9 (4)
C117—C123—C124—C1252.7 (13)O22—Ni—N41—C4157.5 (4)
C123—C124—C125—C1265.9 (18)O12—Ni—N41—C41124.7 (4)
C124—C125—C126—C1272.5 (18)O11—Ni—N41—C4136.7 (4)
C123—C117—C127—C1267.7 (16)O21—Ni—N41—C4536.9 (4)
C118—C117—C127—C12618.3 (13)O22—Ni—N41—C45125.3 (4)
C122—C117—C127—C126119 (3)O12—Ni—N41—C4552.5 (4)
C14—C117—C127—C126179.0 (8)O11—Ni—N41—C45140.5 (4)
C125—C126—C127—C1174.2 (17)C45—N41—C41—C421.2 (7)
O22—Ni—O21—C2111.4 (4)Ni—N41—C41—C42176.1 (4)
O12—Ni—O21—C21168.5 (4)N41—C41—C42—C430.6 (8)
N41—Ni—O21—C2176.9 (4)C41—C42—C43—C440.4 (8)
N31—Ni—O21—C21101.0 (4)C42—C43—C44—C450.6 (8)
O21—Ni—O22—C2317.1 (4)C41—N41—C45—C440.9 (7)
O11—Ni—O22—C23163.6 (4)Ni—N41—C45—C44176.4 (4)
N41—Ni—O22—C2374.9 (4)C43—C44—C45—N410.0 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C34—H34···O12i0.932.863.488 (7)126
C35—H35···O12i0.932.943.524 (6)123
C42—H42···O22ii0.933.143.652 (6)117
C43—H43···O22ii0.932.833.500 (6)130
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Ni(C22H17O2)2(C5H5N)2]
Mr843.60
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)10.8449 (11), 15.2308 (16), 26.770 (2)
β (°) 97.900 (8)
V3)4379.8 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.49
Crystal size (mm)0.2 × 0.1 × 0.1
Data collection
DiffractometerPhilips PW1100
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.879, 0.946
No. of measured, independent and
observed [I > 2σ(I)] reflections
9686, 9483, 3236
Rint0.062
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.159, 0.95
No. of reflections9483
No. of parameters596
No. of restraints18
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

Selected geometric parameters (Å, º) top
Ni—O112.033 (3)Ni—O222.021 (3)
Ni—O122.023 (3)Ni—N312.131 (4)
Ni—O212.003 (3)Ni—N412.103 (4)
O11—Ni—O1288.01 (12)O12—Ni—N4191.58 (14)
O11—Ni—O21177.25 (13)O21—Ni—O2288.47 (12)
O11—Ni—O2294.19 (12)O21—Ni—N3188.30 (14)
O11—Ni—N3191.01 (14)O21—Ni—N4192.00 (14)
O11—Ni—N4188.79 (14)O22—Ni—N3189.55 (14)
O12—Ni—O2189.34 (12)O22—Ni—N4188.39 (13)
O12—Ni—O22177.80 (12)N31—Ni—N41177.91 (16)
O12—Ni—N3190.49 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C34—H34···O12i0.932.863.488 (7)126
C35—H35···O12i0.932.943.524 (6)123
C42—H42···O22ii0.933.143.652 (6)117
C43—H43···O22ii0.932.833.500 (6)130
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+1/2.
 

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