A bis(1-phenyl-1,3-butanedionato)­nickel(II) adduct with 3-amino­pyridine

In the adduct bis(1-phenyl-1,3-butanedionate)­bis(3-amino­pyridine)­nickel(II), [Ni(C₁₀H₉O₂)₂(C₅H₆N₂)₂], the Ni^II atom lies on a crystallographic center of symmetry. The coordination geometry around the Ni^II 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.

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

No syntax errors found



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

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Computing details

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)

Crystal data

[Ni(C10H9O2)2(C5H6N2)2]	F(000) = 596
Mr = 569.29	Dx = 1.412 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4673 reflections
a = 7.546 (2) Å	θ = 2.2–28.7°
b = 17.417 (2) Å	µ = 0.77 mm^−1
c = 10.342 (2) Å	T = 100 K
β = 99.87 (1)°	Needle, green
V = 1339.1 (5) Å^3	0.60 × 0.20 × 0.20 mm
Z = 2

Data collection

Oxford Diffraction Xcalibur CCD diffractometer	3904 independent reflections
Radiation source: fine-focus sealed tube	3214 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
ω scan	θmax = 30.1°, θmin = 4.2°
Absorption correction: analytical (Meulenaer & de Tompa, 1965)	h = −6→10
Tmin = 0.579, Tmax = 0.862	k = −24→24
12114 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0539P)^2 + 0.987P] where P = (Fo^2 + 2Fc^2)/3
3904 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.79 e Å^−3
0 restraints	Δρmin = −0.50 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ni	0.0000	0.0000	0.0000	0.01189 (10)
O2	0.19156 (17)	0.05286 (8)	0.12937 (14)	0.0145 (3)
O1	−0.17169 (17)	0.08909 (8)	0.00902 (13)	0.0148 (3)
N1	0.1093 (2)	0.05068 (10)	−0.15874 (16)	0.0144 (3)
C11	0.2855 (2)	0.06924 (11)	−0.14167 (19)	0.0155 (3)
H11	0.3553	0.0619	−0.0594	0.019*
C4	0.1669 (2)	0.11153 (11)	0.19836 (17)	0.0125 (3)
C10	0.3617 (2)	0.21466 (11)	0.32788 (19)	0.0157 (3)
H10	0.2748	0.2513	0.2978	0.019*
N2	0.5476 (2)	0.12073 (11)	−0.22065 (18)	0.0197 (3)
C1	−0.3159 (2)	0.18934 (12)	0.1049 (2)	0.0182 (4)
H1A	−0.3439	0.2179	0.0246	0.027*
H1B	−0.2901	0.2243	0.1775	0.027*
H1C	−0.4168	0.1578	0.1154	0.027*
C13	0.2612 (2)	0.10862 (12)	−0.3668 (2)	0.0170 (4)
H13	0.3106	0.1280	−0.4366	0.020*
C15	0.0089 (2)	0.05997 (12)	−0.2787 (2)	0.0174 (4)
H15	−0.1122	0.0468	−0.2915	0.021*
C3	0.0034 (2)	0.15153 (11)	0.19381 (19)	0.0153 (3)
H3	−0.0012	0.1890	0.2572	0.018*
C12	0.3680 (2)	0.09926 (11)	−0.24289 (19)	0.0147 (3)
C2	−0.1535 (2)	0.13900 (11)	0.10055 (18)	0.0135 (3)
C6	0.4630 (2)	0.08256 (11)	0.3395 (2)	0.0162 (4)
H6	0.4447	0.0313	0.3158	0.019*
C8	0.6506 (3)	0.18184 (13)	0.4564 (2)	0.0190 (4)
H8	0.7561	0.1965	0.5111	0.023*
C9	0.5214 (2)	0.23680 (12)	0.40832 (19)	0.0173 (4)
H9	0.5417	0.2883	0.4299	0.021*
C5	0.3314 (2)	0.13756 (11)	0.29208 (18)	0.0133 (3)
C14	0.0810 (3)	0.08870 (12)	−0.3841 (2)	0.0191 (4)
H14	0.0084	0.0945	−0.4657	0.023*
C7	0.6209 (3)	0.10447 (12)	0.4220 (2)	0.0195 (4)
H7	0.7066	0.0677	0.4543	0.023*
H1N	0.621 (3)	0.1040 (16)	−0.143 (3)	0.023 (7)*
H2N	0.599 (4)	0.1277 (17)	−0.293 (3)	0.023 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.01143 (15)	0.01246 (17)	0.01154 (17)	−0.00012 (11)	0.00135 (11)	−0.00069 (12)
O2	0.0138 (6)	0.0142 (6)	0.0152 (6)	0.0004 (5)	0.0014 (5)	−0.0025 (5)
O1	0.0140 (6)	0.0156 (7)	0.0146 (6)	0.0020 (5)	0.0016 (5)	0.0007 (5)
N1	0.0141 (7)	0.0140 (7)	0.0149 (7)	0.0000 (5)	0.0022 (6)	0.0001 (6)
C11	0.0162 (8)	0.0157 (9)	0.0137 (8)	−0.0003 (6)	0.0001 (6)	−0.0014 (7)
C4	0.0148 (7)	0.0138 (8)	0.0091 (8)	−0.0015 (6)	0.0025 (6)	0.0015 (6)
C10	0.0170 (8)	0.0149 (9)	0.0155 (8)	0.0012 (6)	0.0036 (6)	−0.0025 (7)
N2	0.0146 (7)	0.0263 (9)	0.0173 (8)	−0.0043 (6)	0.0007 (6)	0.0041 (7)
C1	0.0152 (8)	0.0205 (9)	0.0193 (9)	0.0038 (7)	0.0038 (7)	−0.0006 (7)
C13	0.0179 (8)	0.0174 (9)	0.0159 (9)	0.0010 (7)	0.0031 (7)	0.0029 (7)
C15	0.0144 (8)	0.0203 (10)	0.0171 (9)	−0.0004 (7)	0.0013 (6)	0.0022 (7)
C3	0.0156 (8)	0.0164 (9)	0.0138 (8)	0.0015 (7)	0.0025 (6)	−0.0033 (7)
C12	0.0149 (8)	0.0130 (8)	0.0158 (9)	0.0000 (6)	0.0015 (6)	−0.0011 (7)
C2	0.0133 (7)	0.0148 (8)	0.0131 (8)	0.0007 (6)	0.0045 (6)	0.0028 (6)
C6	0.0170 (8)	0.0131 (9)	0.0178 (9)	−0.0001 (6)	0.0006 (7)	−0.0012 (7)
C8	0.0165 (8)	0.0223 (10)	0.0172 (9)	−0.0022 (7)	0.0002 (7)	−0.0039 (7)
C9	0.0202 (8)	0.0166 (9)	0.0157 (9)	−0.0030 (7)	0.0046 (7)	−0.0053 (7)
C5	0.0131 (7)	0.0156 (9)	0.0109 (8)	0.0000 (6)	0.0013 (6)	−0.0012 (6)
C14	0.0177 (8)	0.0229 (10)	0.0155 (9)	0.0012 (7)	−0.0005 (7)	0.0033 (8)
C7	0.0162 (8)	0.0209 (10)	0.0194 (10)	0.0020 (7)	−0.0028 (7)	−0.0010 (8)

Geometric parameters (Å, º)

Ni—O2	2.0160 (14)	C1—H1B	0.96
Ni—O1	2.0338 (14)	C1—H1C	0.96
Ni—N1	2.1490 (16)	C13—C14	1.385 (3)
O2—C4	1.278 (2)	C13—C12	1.402 (3)
O1—C2	1.275 (2)	C13—H13	0.93
N1—C15	1.348 (3)	C15—C14	1.391 (3)
N1—C11	1.350 (2)	C15—H15	0.93
C11—C12	1.408 (3)	C3—C2	1.410 (3)
C11—H11	0.93	C3—H3	0.93
C4—C3	1.410 (2)	C6—C7	1.394 (3)
C4—C5	1.508 (2)	C6—C5	1.406 (3)
C10—C9	1.396 (3)	C6—H6	0.93
C10—C5	1.401 (3)	C8—C9	1.396 (3)
C10—H10	0.93	C8—C7	1.402 (3)
N2—C12	1.386 (2)	C8—H8	0.93
N2—H1N	0.94 (3)	C9—H9	0.93
N2—H2N	0.91 (3)	C14—H14	0.93
C1—C2	1.514 (2)	C7—H7	0.93
C1—H1A	0.96
O2—Ni—O1	90.63 (5)	N1—C15—H15	119.0
O2—Ni—N1	89.66 (6)	C14—C15—H15	119.0
O1—Ni—N1	93.01 (6)	C4—C3—C2	124.99 (18)
C4—O2—Ni	125.40 (11)	C4—C3—H3	117.5
C2—O1—Ni	124.45 (12)	C2—C3—H3	117.5
C15—N1—C11	118.49 (16)	N2—C12—C13	120.87 (17)
C15—N1—Ni	121.59 (12)	N2—C12—C11	121.44 (18)
C11—N1—Ni	119.78 (13)	C13—C12—C11	117.68 (17)
N1—C11—C12	122.91 (18)	O1—C2—C3	125.76 (17)
N1—C11—H11	118.5	O1—C2—C1	115.60 (16)
C12—C11—H11	118.5	C3—C2—C1	118.64 (17)
O2—C4—C3	125.91 (17)	C7—C6—C5	120.36 (18)
O2—C4—C5	114.63 (15)	C7—C6—H6	119.8
C3—C4—C5	119.46 (16)	C5—C6—H6	119.8
C9—C10—C5	120.47 (18)	C9—C8—C7	119.81 (18)
C9—C10—H10	119.8	C9—C8—H8	120.1
C5—C10—H10	119.8	C7—C8—H8	120.1
C12—N2—H1N	118.3 (16)	C8—C9—C10	120.12 (18)
C12—N2—H2N	116.2 (18)	C8—C9—H9	119.9
H1N—N2—H2N	118 (2)	C10—C9—H9	119.9
C2—C1—H1A	109.5	C10—C5—C6	119.15 (17)
C2—C1—H1B	109.5	C10—C5—C4	122.48 (16)
H1A—C1—H1B	109.5	C6—C5—C4	118.28 (17)
C2—C1—H1C	109.5	C13—C14—C15	119.75 (18)
H1A—C1—H1C	109.5	C13—C14—H14	120.1
H1B—C1—H1C	109.5	C15—C14—H14	120.1
C14—C13—C12	119.12 (18)	C6—C7—C8	120.06 (19)
C14—C13—H13	120.4	C6—C7—H7	120.0
C12—C13—H13	120.4	C8—C7—H7	120.0
N1—C15—C14	122.05 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O1^i	0.94 (3)	2.04 (3)	2.951 (2)	164 (2)
C11—H11···O2	0.93	2.49	3.020 (2)	117
C15—H15···O2^ii	0.93	2.55	3.055 (2)	114

Symmetry codes: (i) x+1, y, z; (ii) −x, −y, −z.