[2,6-Bis(di-tert-butyl-phosphinometh-yl)-phen-yl-κP,C,P'](nitrato-κO)nickel(II).

The Ni(II) atom in the title compound, [Ni(C(24)H(43)P(2))(NO(3))], adopts a distorted square-planar geometry with the P atoms in a trans arrangement. The compound contains a twofold rotational axis with the nitrate group offset from this axis, except for an O atom of the nitrate group, generating two positions of 50% occupancy for the other atoms of the nitrate group.

Related literature

The synthetic preparation was adopted from that employed to prepare the Pd analogue (Cámpora et al., 2004 ▶). For the crystallographic characterization of the Pd analogue, see: Olsson et al. (2007 ▶). For the crystallographic characterization of the starting {2,6-bis­[(di-tert-butyl­phosphino)meth­yl]phenyl}chloridonickel complex, see: Boro et al. (2008 ▶). For related literature, see: Denney et al. (2006 ▶); Johansson et al. (2007 ▶); Keith et al. (2006 ▶).

Experimental

Crystal data

[Ni(C24H43P2)(NO3)]

M = 514.24

Orthorhombic,

a = 24.0023 (14) Å

b = 12.6350 (6) Å

c = 17.6528 (6) Å

V = 5353.5 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.87 mm−1

T = 225 (2) K

0.50 × 0.40 × 0.20 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.671, T max = 0.846

33484 measured reflections

4078 independent reflections

3703 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.099

S = 0.81

4078 reflections

156 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.38 e Å−3

Absolute structure: Flack (1983 ▶), 1976 Freidel pairs

Flack parameter: 0.012 (10)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032376/at2643sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032376/at2643Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C24H43P2)(NO3)]	F(000) = 2208
Mr = 514.24	Dx = 1.276 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 9535 reflections
a = 24.0023 (14) Å	θ = 2.2–30.3°
b = 12.6350 (6) Å	µ = 0.87 mm−1
c = 17.6528 (6) Å	T = 225 K
V = 5353.5 (4) Å3	Cut-prism, orange–brown
Z = 8	0.50 × 0.40 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	4078 independent reflections
Radiation source: fine-focus sealed tube	3703 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 30.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −34→34
Tmin = 0.671, Tmax = 0.846	k = −18→18
33484 measured reflections	l = −25→25

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.1P)2 + 0.25P] where P = (Fo2 + 2Fc2)/3
S = 0.81	(Δ/σ)max = 0.001
4078 reflections	Δρmax = 0.38 e Å−3
156 parameters	Δρmin = −0.38 e Å−3
1 restraint	Absolute structure: Flack (1983), 1976 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.012 (10)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	0.2500	0.2500	0.594610 (14)	0.02536 (9)
P1	0.232841 (19)	0.07823 (3)	0.58242 (3)	0.02639 (10)
C1	0.2500	0.2500	0.48634 (16)	0.0263 (5)
C2	0.22870 (9)	0.16438 (14)	0.44415 (10)	0.0293 (3)
C3	0.22918 (11)	0.16401 (17)	0.36544 (11)	0.0381 (4)
H3	0.2153	0.1051	0.3390	0.046*
C4	0.2500	0.2500	0.32575 (19)	0.0443 (8)
H4	0.2500	0.2500	0.2725	0.053*
C5	0.20438 (10)	0.07210 (16)	0.48626 (12)	0.0357 (4)
H5A	0.2149	0.0054	0.4618	0.043*
H5B	0.1636	0.0770	0.4875	0.043*
C6	0.17578 (10)	0.02125 (17)	0.64252 (13)	0.0356 (4)
C7	0.15103 (12)	−0.08133 (18)	0.60934 (17)	0.0492 (6)
H7A	0.1803	−0.1337	0.6038	0.074*
H7B	0.1348	−0.0665	0.5602	0.074*
H7C	0.1225	−0.1082	0.6431	0.074*
C8	0.13040 (11)	0.1061 (2)	0.64349 (17)	0.0490 (5)
H8A	0.1001	0.0833	0.6759	0.073*
H8B	0.1166	0.1170	0.5925	0.073*
H8C	0.1458	0.1718	0.6627	0.073*
C9	0.19464 (14)	0.00157 (19)	0.72359 (15)	0.0484 (6)
H9A	0.1623	−0.0057	0.7561	0.073*
H9B	0.2171	0.0607	0.7408	0.073*
H9C	0.2166	−0.0628	0.7256	0.073*
C10	0.29710 (10)	−0.00713 (16)	0.58017 (16)	0.0434 (5)
C11	0.33545 (12)	0.0368 (3)	0.5189 (2)	0.0635 (9)
H11A	0.3615	−0.0176	0.5032	0.095*
H11B	0.3558	0.0970	0.5388	0.095*
H11C	0.3134	0.0590	0.4757	0.095*
C12	0.32896 (19)	0.0019 (4)	0.6540 (3)	0.100 (2)
H12A	0.3293	−0.0663	0.6793	0.150*
H12B	0.3110	0.0538	0.6864	0.150*
H12C	0.3669	0.0240	0.6437	0.150*
C13	0.28517 (17)	−0.1214 (3)	0.5629 (4)	0.106 (2)
H13A	0.2705	−0.1274	0.5118	0.159*
H13B	0.2580	−0.1484	0.5986	0.159*
H13C	0.3193	−0.1621	0.5670	0.159*
N1	0.2619 (2)	0.2312 (5)	0.7546 (2)	0.0478 (13)	0.50
O1	0.22947 (16)	0.2640 (3)	0.70255 (19)	0.0394 (7)	0.50
O2	0.3061 (2)	0.1884 (5)	0.7355 (3)	0.0732 (13)	0.50
O3	0.2500	0.2500	0.8206 (2)	0.0869 (14)

	U11	U22	U33	U12	U13	U23
Ni1	0.03377 (16)	0.01934 (13)	0.02296 (14)	−0.00129 (11)	0.000	0.000
P1	0.0305 (2)	0.01967 (19)	0.0290 (2)	0.00015 (15)	0.00072 (17)	0.00082 (15)
C1	0.0312 (13)	0.0241 (12)	0.0238 (11)	0.0033 (8)	0.000	0.000
C2	0.0344 (8)	0.0280 (8)	0.0256 (8)	0.0006 (7)	−0.0019 (7)	−0.0025 (6)
C3	0.0478 (11)	0.0397 (11)	0.0267 (9)	−0.0013 (8)	−0.0025 (8)	−0.0070 (7)
C4	0.059 (2)	0.0497 (19)	0.0237 (12)	0.0046 (13)	0.000	0.000
C5	0.0468 (11)	0.0289 (9)	0.0314 (9)	−0.0077 (8)	−0.0027 (8)	−0.0030 (7)
C6	0.0378 (10)	0.0323 (8)	0.0368 (10)	−0.0059 (8)	0.0047 (8)	0.0017 (7)
C7	0.0514 (13)	0.0399 (11)	0.0564 (14)	−0.0172 (10)	0.0099 (11)	−0.0066 (9)
C8	0.0387 (11)	0.0530 (13)	0.0552 (14)	0.0026 (10)	0.0096 (10)	−0.0039 (11)
C9	0.0621 (16)	0.0468 (14)	0.0364 (11)	−0.0120 (11)	0.0025 (10)	0.0099 (9)
C10	0.0380 (10)	0.0317 (10)	0.0606 (15)	0.0095 (7)	0.0119 (10)	0.0072 (9)
C11	0.0397 (12)	0.0590 (16)	0.092 (2)	0.0147 (12)	0.0217 (15)	0.0184 (17)
C12	0.061 (2)	0.168 (6)	0.070 (3)	0.056 (3)	−0.0012 (18)	0.028 (2)
C13	0.069 (2)	0.0339 (14)	0.215 (7)	0.0129 (13)	0.034 (3)	−0.011 (2)
N1	0.057 (4)	0.052 (4)	0.0350 (19)	−0.016 (2)	−0.0114 (18)	0.0079 (18)
O1	0.0488 (17)	0.0462 (17)	0.0233 (14)	−0.0022 (15)	0.0012 (13)	−0.0048 (12)
O2	0.054 (2)	0.104 (4)	0.062 (3)	0.012 (3)	−0.011 (2)	0.019 (3)
O3	0.098 (3)	0.137 (4)	0.0265 (13)	−0.012 (2)	0.000	0.000

Ni1—C1	1.911 (3)	C7—H7C	0.9700
Ni1—O1i	1.976 (3)	C8—H8A	0.9700
Ni1—O1	1.976 (3)	C8—H8B	0.9700
Ni1—P1i	2.2195 (4)	C8—H8C	0.9700
Ni1—P1	2.2195 (4)	C9—H9A	0.9700
P1—C5	1.831 (2)	C9—H9B	0.9700
P1—C6	1.876 (2)	C9—H9C	0.9700
P1—C10	1.882 (2)	C10—C13	1.503 (4)
C1—C2i	1.409 (2)	C10—C12	1.516 (6)
C1—C2	1.409 (2)	C10—C11	1.525 (4)
C2—C3	1.389 (3)	C11—H11A	0.9700
C2—C5	1.501 (3)	C11—H11B	0.9700
C3—C4	1.386 (3)	C11—H11C	0.9700
C3—H3	0.9400	C12—H12A	0.9700
C4—C3i	1.386 (3)	C12—H12B	0.9700
C4—H4	0.9400	C12—H12C	0.9700
C5—H5A	0.9800	C13—H13A	0.9700
C5—H5B	0.9800	C13—H13B	0.9700
C6—C9	1.521 (3)	C13—H13C	0.9700
C6—C8	1.528 (4)	N1—O3	1.223 (5)
C6—C7	1.541 (3)	N1—O2	1.239 (7)
C7—H7A	0.9700	N1—O1	1.273 (5)
C7—H7B	0.9700	O3—N1i	1.223 (5)
C1—Ni1—O1i	164.64 (11)	C6—C8—H8B	109.5
C1—Ni1—O1	164.64 (11)	H8A—C8—H8B	109.5
C1—Ni1—P1i	84.437 (14)	C6—C8—H8C	109.5
O1i—Ni1—P1i	97.74 (10)	H8A—C8—H8C	109.5
O1—Ni1—P1i	93.00 (10)	H8B—C8—H8C	109.5
C1—Ni1—P1	84.435 (14)	C6—C9—H9A	109.5
O1i—Ni1—P1	93.00 (10)	C6—C9—H9B	109.5
O1—Ni1—P1	97.74 (10)	H9A—C9—H9B	109.5
P1i—Ni1—P1	168.87 (3)	C6—C9—H9C	109.5
C5—P1—C6	103.63 (10)	H9A—C9—H9C	109.5
C5—P1—C10	105.18 (12)	H9B—C9—H9C	109.5
C6—P1—C10	112.97 (10)	C13—C10—C12	110.1 (3)
C5—P1—Ni1	101.56 (7)	C13—C10—C11	108.7 (3)
C6—P1—Ni1	117.12 (7)	C12—C10—C11	106.1 (3)
C10—P1—Ni1	114.22 (8)	C13—C10—P1	113.5 (2)
C2i—C1—C2	116.2 (3)	C12—C10—P1	110.6 (2)
C2i—C1—Ni1	121.90 (13)	C11—C10—P1	107.52 (16)
C2—C1—Ni1	121.90 (13)	C10—C11—H11A	109.5
C3—C2—C1	121.9 (2)	C10—C11—H11B	109.5
C3—C2—C5	119.73 (18)	H11A—C11—H11B	109.5
C1—C2—C5	118.39 (19)	C10—C11—H11C	109.5
C4—C3—C2	120.4 (2)	H11A—C11—H11C	109.5
C4—C3—H3	119.8	H11B—C11—H11C	109.5
C2—C3—H3	119.8	C10—C12—H12A	109.5
C3i—C4—C3	119.3 (3)	C10—C12—H12B	109.5
C3i—C4—H4	120.4	H12A—C12—H12B	109.5
C3—C4—H4	120.4	C10—C12—H12C	109.5
C2—C5—P1	106.33 (13)	H12A—C12—H12C	109.5
C2—C5—H5A	110.5	H12B—C12—H12C	109.5
P1—C5—H5A	110.5	C10—C13—H13A	109.5
C2—C5—H5B	110.5	C10—C13—H13B	109.5
P1—C5—H5B	110.5	H13A—C13—H13B	109.5
H5A—C5—H5B	108.7	C10—C13—H13C	109.5
C9—C6—C8	108.4 (2)	H13A—C13—H13C	109.5
C9—C6—C7	109.6 (2)	H13B—C13—H13C	109.5
C8—C6—C7	108.6 (2)	O1i—N1—O3	165.1 (6)
C9—C6—P1	112.18 (18)	O1i—N1—O2	64.8 (4)
C8—C6—P1	104.93 (15)	O3—N1—O2	123.0 (4)
C7—C6—P1	112.90 (16)	O3—N1—O1	118.8 (4)
C6—C7—H7A	109.5	O2—N1—O1	117.9 (5)
C6—C7—H7B	109.5	N1i—O1—O2i	69.6 (4)
H7A—C7—H7B	109.5	O2i—O1—N1	104.4 (4)
C6—C7—H7C	109.5	N1i—O1—Ni1	152.8 (5)
H7A—C7—H7C	109.5	O2i—O1—Ni1	133.8 (4)
H7B—C7—H7C	109.5	N1—O1—Ni1	121.0 (3)
C6—C8—H8A	109.5