Bis(adamantylamine-κN)bis­(1-phenyl­butane-1,3-dionato-κ²O,O′)nickel(II)

In the title complex, [Ni(C₁₀H₉O₂)₂(C₁₀H₁₇N)₂], the Ni atom, which occupies a special position at an inversion centre, has an octa­hedral environment formed by four O atoms of two chelate benzoyl­acetonates [Ni—O 2.0409 (16) and 2.0187 (16) Å, and O—Ni—O 90.36 (6)°] and two N atoms of the adamantylamine ligands [Ni—N = 2.176 (2) Å]. The amine H atoms of the adamantylamine ligands do not participate in any hydrogen bonds, due to their steric shielding and the lack of accessible acceptors.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.103
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N      -   H1N    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N      -   H2N    ...          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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 RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; 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); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(adamantylamine-κN)bis(1-phenylbutane-1,3-dionato-κO,O')nickel(II)

Crystal data

[Ni(C10H9O2)2(C10H17N)2]	Z = 1
Mr = 683.55	F(000) = 366
Triclinic, P1	Dx = 1.271 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.738 (3) Å	Cell parameters from 4811 reflections
b = 12.028 (3) Å	θ = 2.1–30.4°
c = 12.063 (3) Å	µ = 0.59 mm^−1
α = 70.02 (3)°	T = 295 K
β = 86.88 (3)°	Plate, green
γ = 76.45 (3)°	0.6 × 0.3 × 0.1 mm
V = 892.8 (5) Å^3

Data collection

Oxford Diffraction Xcalibur 3 CCD area-detector diffractometer	3129 independent reflections
Radiation source: fine-focus sealed tube	2545 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scans	θmax = 25.0°, θmin = 4.2°
Absorption correction: analytical (Alcock, 1970)	h = −8→8
Tmin = 0.810, Tmax = 0.941	k = −14→14
12713 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.057P)^2] where P = (Fo^2 + 2Fc^2)/3
3129 reflections	(Δ/σ)max < 0.001
215 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.26 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	1.0000	0.0000	0.0000	0.04476 (18)
O1	1.1488 (2)	0.13748 (13)	−0.06614 (13)	0.0474 (4)
O2	0.7838 (2)	0.10678 (13)	0.06509 (13)	0.0471 (4)
N	1.2002 (3)	−0.04761 (17)	0.15284 (16)	0.0507 (5)
H1N	1.3261	−0.0727	0.1285	0.061*
H2N	1.1989	0.0238	0.1619	0.061*
C1	1.2466 (4)	0.3200 (2)	−0.0943 (3)	0.0687 (8)
H1A	1.3868	0.2765	−0.0785	0.103*
H1C	1.2194	0.3833	−0.0603	0.103*
H1B	1.2211	0.3551	−0.1780	0.103*
C2	1.1097 (3)	0.2340 (2)	−0.0411 (2)	0.0464 (5)
C3	0.9510 (4)	0.2669 (2)	0.0286 (2)	0.0538 (6)
H3	0.9482	0.3366	0.0464	0.065*
C4	0.7962 (3)	0.20688 (19)	0.07441 (18)	0.0424 (5)
C5	0.6233 (3)	0.2615 (2)	0.13816 (19)	0.0443 (5)
C6	0.4898 (4)	0.1919 (2)	0.1984 (2)	0.0557 (6)
H6	0.5124	0.1113	0.2024	0.067*
C7	0.3237 (4)	0.2402 (3)	0.2527 (2)	0.0691 (7)
H7	0.2362	0.1918	0.2939	0.083*
C8	0.2865 (4)	0.3597 (3)	0.2461 (2)	0.0711 (8)
H8	0.1724	0.3930	0.2812	0.085*
C9	0.4182 (5)	0.4290 (3)	0.1879 (3)	0.0782 (8)
H9	0.3944	0.5096	0.1839	0.094*
C10	0.5866 (4)	0.3807 (2)	0.1348 (2)	0.0663 (7)
H10	0.6764	0.4287	0.0963	0.080*
C11	1.1935 (3)	−0.13326 (19)	0.27463 (18)	0.0421 (5)
C12	0.9817 (4)	−0.1023 (2)	0.3217 (2)	0.0568 (6)
H12A	0.8802	−0.1063	0.2701	0.068*
H12B	0.9531	−0.0201	0.3239	0.068*
C13	0.9698 (4)	−0.1921 (3)	0.4462 (2)	0.0703 (8)
H13	0.8329	−0.1720	0.4763	0.084*
C14	1.0120 (4)	−0.3199 (3)	0.4415 (2)	0.0746 (8)
H14A	1.0016	−0.3772	0.5197	0.090*
H14B	0.9118	−0.3250	0.3897	0.090*
C15	1.2238 (4)	−0.3517 (2)	0.3963 (2)	0.0580 (6)
H15	1.2506	−0.4343	0.3933	0.070*
C16	1.2359 (4)	−0.2623 (2)	0.2723 (2)	0.0500 (6)
H16A	1.3707	−0.2828	0.2419	0.060*
H16B	1.1366	−0.2679	0.2203	0.060*
C17	1.3522 (4)	−0.1274 (2)	0.3572 (2)	0.0612 (7)
H17A	1.4877	−0.1472	0.3274	0.073*
H17B	1.3280	−0.0455	0.3595	0.073*
C18	1.1275 (5)	−0.1851 (3)	0.5277 (2)	0.0780 (9)
H18B	1.1001	−0.1038	0.5318	0.094*
H18A	1.1189	−0.2416	0.6066	0.094*
C19	1.3819 (4)	−0.3451 (2)	0.4777 (2)	0.0628 (7)
H19B	1.5179	−0.3665	0.4490	0.075*
H19A	1.3747	−0.4022	0.5564	0.075*
C20	1.3403 (4)	−0.2163 (2)	0.4814 (2)	0.0621 (7)
H20	1.4417	−0.2111	0.5336	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.0561 (3)	0.0350 (2)	0.0437 (3)	−0.01306 (18)	0.00447 (19)	−0.01273 (18)
O1	0.0563 (10)	0.0419 (9)	0.0455 (9)	−0.0160 (7)	0.0056 (7)	−0.0142 (7)
O2	0.0530 (9)	0.0386 (8)	0.0538 (9)	−0.0164 (7)	0.0085 (7)	−0.0177 (7)
N	0.0599 (12)	0.0450 (11)	0.0485 (11)	−0.0182 (9)	0.0016 (9)	−0.0133 (9)
C1	0.0774 (18)	0.0589 (16)	0.080 (2)	−0.0354 (14)	0.0188 (15)	−0.0264 (14)
C2	0.0517 (14)	0.0423 (13)	0.0472 (13)	−0.0153 (10)	−0.0031 (11)	−0.0141 (11)
C3	0.0623 (15)	0.0437 (13)	0.0656 (16)	−0.0208 (11)	0.0085 (12)	−0.0264 (12)
C4	0.0504 (13)	0.0370 (12)	0.0402 (12)	−0.0116 (10)	−0.0011 (10)	−0.0121 (9)
C5	0.0525 (14)	0.0411 (12)	0.0404 (12)	−0.0098 (10)	−0.0029 (10)	−0.0151 (10)
C6	0.0608 (16)	0.0512 (14)	0.0598 (16)	−0.0176 (12)	0.0098 (12)	−0.0227 (12)
C7	0.0706 (18)	0.0729 (19)	0.0677 (18)	−0.0205 (14)	0.0209 (14)	−0.0291 (15)
C8	0.0768 (19)	0.0722 (19)	0.0621 (17)	−0.0018 (15)	0.0148 (14)	−0.0320 (15)
C9	0.100 (2)	0.0541 (16)	0.084 (2)	−0.0104 (16)	0.0244 (17)	−0.0351 (15)
C10	0.0839 (19)	0.0468 (15)	0.0741 (19)	−0.0200 (13)	0.0216 (15)	−0.0275 (13)
C11	0.0477 (13)	0.0372 (11)	0.0400 (12)	−0.0085 (9)	0.0008 (10)	−0.0121 (9)
C12	0.0589 (15)	0.0546 (15)	0.0465 (14)	0.0081 (11)	0.0004 (11)	−0.0178 (11)
C13	0.0570 (16)	0.088 (2)	0.0473 (15)	0.0041 (14)	0.0123 (13)	−0.0156 (14)
C14	0.0750 (19)	0.080 (2)	0.0558 (17)	−0.0296 (15)	0.0060 (14)	0.0006 (14)
C15	0.0747 (17)	0.0373 (13)	0.0579 (15)	−0.0091 (11)	−0.0029 (13)	−0.0126 (11)
C16	0.0534 (14)	0.0444 (13)	0.0518 (14)	−0.0034 (10)	0.0025 (11)	−0.0210 (11)
C17	0.0719 (17)	0.0494 (14)	0.0619 (16)	−0.0173 (12)	−0.0150 (13)	−0.0136 (12)
C18	0.105 (2)	0.0722 (19)	0.0447 (15)	0.0062 (16)	−0.0003 (15)	−0.0217 (14)
C19	0.0655 (16)	0.0507 (15)	0.0562 (16)	0.0010 (12)	−0.0079 (13)	−0.0063 (12)
C20	0.0758 (18)	0.0562 (15)	0.0511 (15)	−0.0108 (13)	−0.0195 (13)	−0.0137 (12)

Geometric parameters (Å, º)

Ni—O2^i	2.0187 (16)	C10—H10	0.9300
Ni—O1	2.0409 (16)	C11—C12	1.519 (3)
Ni—O2	2.0187 (16)	C11—C16	1.520 (3)
Ni—O1^i	2.0409 (16)	C11—C17	1.529 (3)
Ni—N	2.176 (2)	C12—C13	1.532 (3)
Ni—N^i	2.176 (2)	C12—H12A	0.9700
O1—C2	1.263 (3)	C12—H12B	0.9700
O2—C4	1.269 (3)	C13—C14	1.516 (4)
N—C11	1.484 (3)	C13—C18	1.522 (4)
N—H1N	0.9000	C13—H13	0.9800
N—H2N	0.9000	C14—C15	1.511 (4)
C1—C2	1.505 (3)	C14—H14A	0.9700
C1—H1A	0.9600	C14—H14B	0.9700
C1—H1C	0.9600	C15—C19	1.521 (4)
C1—H1B	0.9600	C15—C16	1.526 (3)
C2—C3	1.392 (3)	C15—H15	0.9800
C3—C4	1.390 (3)	C16—H16A	0.9700
C3—H3	0.9300	C16—H16B	0.9700
C4—C5	1.506 (3)	C17—C20	1.526 (3)
C5—C6	1.380 (3)	C17—H17A	0.9700
C5—C10	1.383 (3)	C17—H17B	0.9700
C6—C7	1.376 (3)	C18—C20	1.521 (4)
C6—H6	0.9300	C18—H18B	0.9700
C7—C8	1.376 (4)	C18—H18A	0.9700
C7—H7	0.9300	C19—C20	1.524 (4)
C8—C9	1.362 (4)	C19—H19B	0.9700
C8—H8	0.9300	C19—H19A	0.9700
C9—C10	1.379 (4)	C20—H20	0.9800
C9—H9	0.9300
O2^i—Ni—O2	180.00 (12)	C12—C11—C16	109.00 (19)
O2^i—Ni—O1^i	90.36 (6)	N—C11—C17	112.02 (18)
O2—Ni—O1^i	89.64 (6)	C12—C11—C17	109.3 (2)
O2^i—Ni—O1	89.64 (6)	C16—C11—C17	108.34 (19)
O2—Ni—O1	90.36 (6)	C11—C12—C13	109.60 (19)
O1^i—Ni—O1	180.00 (6)	C11—C12—H12A	109.7
O2^i—Ni—N	88.90 (7)	C13—C12—H12A	109.7
O2—Ni—N	91.10 (7)	C11—C12—H12B	109.7
O1^i—Ni—N	97.28 (7)	C13—C12—H12B	109.7
O1—Ni—N	82.72 (7)	H12A—C12—H12B	108.2
O2^i—Ni—N^i	91.10 (7)	C14—C13—C18	109.4 (2)
O2—Ni—N^i	88.90 (7)	C14—C13—C12	109.3 (2)
O1^i—Ni—N^i	82.72 (7)	C18—C13—C12	109.9 (2)
O1—Ni—N^i	97.28 (7)	C14—C13—H13	109.4
N—Ni—N^i	180.00 (6)	C18—C13—H13	109.4
C2—O1—Ni	124.67 (14)	C12—C13—H13	109.4
C4—O2—Ni	125.71 (14)	C15—C14—C13	109.5 (2)
C11—N—Ni	130.22 (14)	C15—C14—H14A	109.8
C11—N—H1N	104.7	C13—C14—H14A	109.8
Ni—N—H1N	104.7	C15—C14—H14B	109.8
C11—N—H2N	104.7	C13—C14—H14B	109.8
Ni—N—H2N	104.7	H14A—C14—H14B	108.2
H1N—N—H2N	105.7	C14—C15—C19	110.1 (2)
C2—C1—H1A	109.5	C14—C15—C16	109.0 (2)
C2—C1—H1C	109.5	C19—C15—C16	109.9 (2)
H1A—C1—H1C	109.5	C14—C15—H15	109.3
C2—C1—H1B	109.5	C19—C15—H15	109.3
H1A—C1—H1B	109.5	C16—C15—H15	109.3
H1C—C1—H1B	109.5	C11—C16—C15	110.23 (19)
O1—C2—C3	125.6 (2)	C11—C16—H16A	109.6
O1—C2—C1	115.8 (2)	C15—C16—H16A	109.6
C3—C2—C1	118.5 (2)	C11—C16—H16B	109.6
C4—C3—C2	127.1 (2)	C15—C16—H16B	109.6
C4—C3—H3	116.5	H16A—C16—H16B	108.1
C2—C3—H3	116.5	C20—C17—C11	110.5 (2)
O2—C4—C3	124.8 (2)	C20—C17—H17A	109.6
O2—C4—C5	114.84 (19)	C11—C17—H17A	109.6
C3—C4—C5	120.4 (2)	C20—C17—H17B	109.6
C6—C5—C10	118.2 (2)	C11—C17—H17B	109.6
C6—C5—C4	119.0 (2)	H17A—C17—H17B	108.1
C10—C5—C4	122.8 (2)	C20—C18—C13	109.7 (2)
C7—C6—C5	120.9 (2)	C20—C18—H18B	109.7
C7—C6—H6	119.5	C13—C18—H18B	109.7
C5—C6—H6	119.6	C20—C18—H18A	109.7
C6—C7—C8	120.3 (3)	C13—C18—H18A	109.7
C6—C7—H7	119.9	H18B—C18—H18A	108.2
C8—C7—H7	119.9	C15—C19—C20	109.1 (2)
C9—C8—C7	119.4 (2)	C15—C19—H19B	109.9
C9—C8—H8	120.3	C20—C19—H19B	109.9
C7—C8—H8	120.3	C15—C19—H19A	109.9
C8—C9—C10	120.6 (3)	C20—C19—H19A	109.9
C8—C9—H9	119.7	H19B—C19—H19A	108.3
C10—C9—H9	119.7	C18—C20—C19	109.0 (2)
C9—C10—C5	120.7 (2)	C18—C20—C17	109.4 (2)
C9—C10—H10	119.7	C19—C20—C17	109.4 (2)
C5—C10—H10	119.7	C18—C20—H20	109.7
N—C11—C12	108.83 (18)	C19—C20—H20	109.7
N—C11—C16	109.31 (18)	C17—C20—H20	109.7

Symmetry code: (i) −x+2, −y, −z.