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In the adduct bis(1-phenyl-1,3-butanedionate)­bis(3-amino­pyridine)­nickel(II), [Ni(C10H9O2)2(C5H6N2)2], the NiII atom lies on a crystallographic center of symmetry. The coordination geometry around the NiII atom is distorted octahedral. Four O atoms of two 1-phenyl-1,3-butanedionate ligands form the equatorial plane, with Ni—O distances in the range 2.0160 (14)–2.0338 (14) Å. The axial positions are occupied by N atoms of two 3-amino­pyridine ligands. The adduct mol­ecules translated by one unit along the a axis are linked by N—H...O hydrogen bonds, forming chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021111/ci6276sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021111/ci6276Isup2.hkl
Contains datablock I

CCDC reference: 226643

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.116
  • Data-to-parameter ratio = 21.0

checkCIF/PLATON results

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Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.99
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2N ... ?
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C30 H30 N4 Ni1 O4 Atom count from _chemical_formula_moiety:C25 H24 N2 Ni1 O4.2
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST97 (Nardelli, 1995).

Bis(1-phenyl-1,3-butandionate)bis(3-aminopyridine)nickel(II) top
Crystal data top
[Ni(C10H9O2)2(C5H6N2)2]F(000) = 596
Mr = 569.29Dx = 1.412 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4673 reflections
a = 7.546 (2) Åθ = 2.2–28.7°
b = 17.417 (2) ŵ = 0.77 mm1
c = 10.342 (2) ÅT = 100 K
β = 99.87 (1)°Needle, green
V = 1339.1 (5) Å30.60 × 0.20 × 0.20 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur CCD
diffractometer
3904 independent reflections
Radiation source: fine-focus sealed tube3214 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
ω scanθmax = 30.1°, θmin = 4.2°
Absorption correction: analytical
(Meulenaer & de Tompa, 1965)
h = 610
Tmin = 0.579, Tmax = 0.862k = 2424
12114 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0539P)2 + 0.987P]
where P = (Fo2 + 2Fc2)/3
3904 reflections(Δ/σ)max < 0.001
186 parametersΔρmax = 0.79 e Å3
0 restraintsΔρmin = 0.50 e Å3
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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni0.00000.00000.00000.01189 (10)
O20.19156 (17)0.05286 (8)0.12937 (14)0.0145 (3)
O10.17169 (17)0.08909 (8)0.00902 (13)0.0148 (3)
N10.1093 (2)0.05068 (10)0.15874 (16)0.0144 (3)
C110.2855 (2)0.06924 (11)0.14167 (19)0.0155 (3)
H110.35530.06190.05940.019*
C40.1669 (2)0.11153 (11)0.19836 (17)0.0125 (3)
C100.3617 (2)0.21466 (11)0.32788 (19)0.0157 (3)
H100.27480.25130.29780.019*
N20.5476 (2)0.12073 (11)0.22065 (18)0.0197 (3)
C10.3159 (2)0.18934 (12)0.1049 (2)0.0182 (4)
H1A0.34390.21790.02460.027*
H1B0.29010.22430.17750.027*
H1C0.41680.15780.11540.027*
C130.2612 (2)0.10862 (12)0.3668 (2)0.0170 (4)
H130.31060.12800.43660.020*
C150.0089 (2)0.05997 (12)0.2787 (2)0.0174 (4)
H150.11220.04680.29150.021*
C30.0034 (2)0.15153 (11)0.19381 (19)0.0153 (3)
H30.00120.18900.25720.018*
C120.3680 (2)0.09926 (11)0.24289 (19)0.0147 (3)
C20.1535 (2)0.13900 (11)0.10055 (18)0.0135 (3)
C60.4630 (2)0.08256 (11)0.3395 (2)0.0162 (4)
H60.44470.03130.31580.019*
C80.6506 (3)0.18184 (13)0.4564 (2)0.0190 (4)
H80.75610.19650.51110.023*
C90.5214 (2)0.23680 (12)0.40832 (19)0.0173 (4)
H90.54170.28830.42990.021*
C50.3314 (2)0.13756 (11)0.29208 (18)0.0133 (3)
C140.0810 (3)0.08870 (12)0.3841 (2)0.0191 (4)
H140.00840.09450.46570.023*
C70.6209 (3)0.10447 (12)0.4220 (2)0.0195 (4)
H70.70660.06770.45430.023*
H1N0.621 (3)0.1040 (16)0.143 (3)0.023 (7)*
H2N0.599 (4)0.1277 (17)0.293 (3)0.023 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni0.01143 (15)0.01246 (17)0.01154 (17)0.00012 (11)0.00135 (11)0.00069 (12)
O20.0138 (6)0.0142 (6)0.0152 (6)0.0004 (5)0.0014 (5)0.0025 (5)
O10.0140 (6)0.0156 (7)0.0146 (6)0.0020 (5)0.0016 (5)0.0007 (5)
N10.0141 (7)0.0140 (7)0.0149 (7)0.0000 (5)0.0022 (6)0.0001 (6)
C110.0162 (8)0.0157 (9)0.0137 (8)0.0003 (6)0.0001 (6)0.0014 (7)
C40.0148 (7)0.0138 (8)0.0091 (8)0.0015 (6)0.0025 (6)0.0015 (6)
C100.0170 (8)0.0149 (9)0.0155 (8)0.0012 (6)0.0036 (6)0.0025 (7)
N20.0146 (7)0.0263 (9)0.0173 (8)0.0043 (6)0.0007 (6)0.0041 (7)
C10.0152 (8)0.0205 (9)0.0193 (9)0.0038 (7)0.0038 (7)0.0006 (7)
C130.0179 (8)0.0174 (9)0.0159 (9)0.0010 (7)0.0031 (7)0.0029 (7)
C150.0144 (8)0.0203 (10)0.0171 (9)0.0004 (7)0.0013 (6)0.0022 (7)
C30.0156 (8)0.0164 (9)0.0138 (8)0.0015 (7)0.0025 (6)0.0033 (7)
C120.0149 (8)0.0130 (8)0.0158 (9)0.0000 (6)0.0015 (6)0.0011 (7)
C20.0133 (7)0.0148 (8)0.0131 (8)0.0007 (6)0.0045 (6)0.0028 (6)
C60.0170 (8)0.0131 (9)0.0178 (9)0.0001 (6)0.0006 (7)0.0012 (7)
C80.0165 (8)0.0223 (10)0.0172 (9)0.0022 (7)0.0002 (7)0.0039 (7)
C90.0202 (8)0.0166 (9)0.0157 (9)0.0030 (7)0.0046 (7)0.0053 (7)
C50.0131 (7)0.0156 (9)0.0109 (8)0.0000 (6)0.0013 (6)0.0012 (6)
C140.0177 (8)0.0229 (10)0.0155 (9)0.0012 (7)0.0005 (7)0.0033 (8)
C70.0162 (8)0.0209 (10)0.0194 (10)0.0020 (7)0.0028 (7)0.0010 (8)
Geometric parameters (Å, º) top
Ni—O22.0160 (14)C1—H1B0.96
Ni—O12.0338 (14)C1—H1C0.96
Ni—N12.1490 (16)C13—C141.385 (3)
O2—C41.278 (2)C13—C121.402 (3)
O1—C21.275 (2)C13—H130.93
N1—C151.348 (3)C15—C141.391 (3)
N1—C111.350 (2)C15—H150.93
C11—C121.408 (3)C3—C21.410 (3)
C11—H110.93C3—H30.93
C4—C31.410 (2)C6—C71.394 (3)
C4—C51.508 (2)C6—C51.406 (3)
C10—C91.396 (3)C6—H60.93
C10—C51.401 (3)C8—C91.396 (3)
C10—H100.93C8—C71.402 (3)
N2—C121.386 (2)C8—H80.93
N2—H1N0.94 (3)C9—H90.93
N2—H2N0.91 (3)C14—H140.93
C1—C21.514 (2)C7—H70.93
C1—H1A0.96
O2—Ni—O190.63 (5)N1—C15—H15119.0
O2—Ni—N189.66 (6)C14—C15—H15119.0
O1—Ni—N193.01 (6)C4—C3—C2124.99 (18)
C4—O2—Ni125.40 (11)C4—C3—H3117.5
C2—O1—Ni124.45 (12)C2—C3—H3117.5
C15—N1—C11118.49 (16)N2—C12—C13120.87 (17)
C15—N1—Ni121.59 (12)N2—C12—C11121.44 (18)
C11—N1—Ni119.78 (13)C13—C12—C11117.68 (17)
N1—C11—C12122.91 (18)O1—C2—C3125.76 (17)
N1—C11—H11118.5O1—C2—C1115.60 (16)
C12—C11—H11118.5C3—C2—C1118.64 (17)
O2—C4—C3125.91 (17)C7—C6—C5120.36 (18)
O2—C4—C5114.63 (15)C7—C6—H6119.8
C3—C4—C5119.46 (16)C5—C6—H6119.8
C9—C10—C5120.47 (18)C9—C8—C7119.81 (18)
C9—C10—H10119.8C9—C8—H8120.1
C5—C10—H10119.8C7—C8—H8120.1
C12—N2—H1N118.3 (16)C8—C9—C10120.12 (18)
C12—N2—H2N116.2 (18)C8—C9—H9119.9
H1N—N2—H2N118 (2)C10—C9—H9119.9
C2—C1—H1A109.5C10—C5—C6119.15 (17)
C2—C1—H1B109.5C10—C5—C4122.48 (16)
H1A—C1—H1B109.5C6—C5—C4118.28 (17)
C2—C1—H1C109.5C13—C14—C15119.75 (18)
H1A—C1—H1C109.5C13—C14—H14120.1
H1B—C1—H1C109.5C15—C14—H14120.1
C14—C13—C12119.12 (18)C6—C7—C8120.06 (19)
C14—C13—H13120.4C6—C7—H7120.0
C12—C13—H13120.4C8—C7—H7120.0
N1—C15—C14122.05 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1N···O1i0.94 (3)2.04 (3)2.951 (2)164 (2)
C11—H11···O20.932.493.020 (2)117
C15—H15···O2ii0.932.553.055 (2)114
Symmetry codes: (i) x+1, y, z; (ii) x, y, z.
 

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