Literature DB >> 21201043

{2,6-Bis[(di-tert-butyl-phosphino)-methyl]-phenyl}chloridonickel(II).

Brian J Boro, Diane A Dickie, Karen I Goldberg, Richard A Kemp.   

Abstract

In the title compound, [Ni(C(24)H(43)P(2))Cl], the Ni atom adopts a distorted square-planar geometry, with the P atoms of the 2,6-bis-[(di-tert-butyl-phosphino)meth-yl]phenyl ligand trans to one another. The P-Ni-P plane is twisted out of the plane of the aromatic ring by 21.97 (6)°.

Entities:  

Year:  2008        PMID： 21201043      PMCID： PMC2959246          DOI： 10.1107/S1600536808029814

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the original synthesis and spectroscopic characterization of the title compound, see: Moulton & Shaw (1976 ▶). For the crystallographic characterization of the Pd analogue, see: Kimmich et al. (2002 ▶). For crystallographic characterization of the 2,6-bis­[(di-tert-butyl­phosphino)meth­yl]benzene ligand, see: Hollink et al. (2003 ▶). For related literature, see: Denney et al. (2006 ▶); Keith et al. (2006 ▶).

Experimental

Crystal data

[Ni(C24H43P2)Cl] M = 487.68 Orthorhombic, a = 11.3394 (4) Å b = 15.0463 (5) Å c = 15.4184 (5) Å V = 2630.63 (15) Å3 Z = 4 Mo Kα radiation μ = 0.97 mm−1 T = 225 (2) K 0.50 × 0.50 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.622, T max = 0.679 84881 measured reflections 10074 independent reflections 8461 reflections with I > 2σ(I) R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.084 S = 1.09 10074 reflections 265 parameters H-atom parameters constrained Δρmax = 0.32 e Å−3 Δρmin = −0.50 e Å−3 Absolute structure: Flack (1983 ▶), with 4507 Friedel pairs Flack parameter: 0.006 (7) Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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/S1600536808029814/pv2105sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029814/pv2105Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Ni(C24H43P2)Cl]F(000) = 1048
Mr = 487.68Dx = 1.231 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 8656 reflections
a = 11.3394 (4) Åθ = 2.2–32.5°
b = 15.0463 (5) ŵ = 0.97 mm−1
c = 15.4184 (5) ÅT = 225 K
V = 2630.63 (15) Å3Prism, gold-brown
Z = 40.50 × 0.50 × 0.40 mm
Bruker SMART CCD area-detector diffractometer10074 independent reflections
Radiation source: fine-focus sealed tube8461 reflections with I > 2σ(I)
graphiteRint = 0.048
φ and ω scansθmax = 33.2°, θmin = 1.9°
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2004)h = −17→17
Tmin = 0.622, Tmax = 0.679k = −23→23
84881 measured reflectionsl = −23→23
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.084w = 1/[σ2(Fo2) + (0.0439P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.002
10074 reflectionsΔρmax = 0.32 e Å−3
265 parametersΔρmin = −0.50 e Å−3
0 restraintsAbsolute structure: Flack (1983), with 4507 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.006 (7)
Experimental. Yield = 60%. 1H NMR (250 MHz, C6D6) δ 7.00 (t, 1H, 3JHH = 7.4 Hz, Ar-Hpara), 6.84 (d, 2H, 3JHH = 7.4 Hz, Ar-Hmeta), 2.91 (virtual t, 4H, JHP = 6.8 Hz, CH2), 1.40 (virtual t, 36H, JHP = 12.7 Hz, CH3) p.p.m. 13C{1H} NMR (63 MHz, C6D6) δ 155.7 (t, 2JCP = 16.7 Hz, Ar-Cipso), 153.0 (virtual t, JCP = 25.5 Hz, Ar-Cortho), 125.2 (s, Ar-Cpara), 121.8 (virtual t, JCP = 16.7 Hz, Ar-Cmeta), 34.9 (virtual t, JCP = 13.4 Hz, PCH2), 34.3 (virtual t, JCP = 22.7 Hz, PC(CH3)3), 29.8 (s, CH3) p.p.m. 31P{1H} NMR (101 MHz, C6D6) δ 66.9 p.p.m.
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.
xyzUiso*/Ueq
Ni10.536566 (17)0.968358 (13)0.925683 (12)0.02623 (5)
Cl10.60025 (5)1.02689 (4)0.80121 (3)0.04914 (12)
P10.38227 (4)0.90497 (3)0.86644 (3)0.02696 (8)
P20.67658 (4)1.02487 (3)1.00738 (3)0.02786 (8)
C10.48595 (14)0.91031 (10)1.03045 (10)0.0278 (3)
C20.37594 (16)0.86671 (11)1.03569 (11)0.0326 (3)
C30.34528 (18)0.81652 (13)1.10805 (13)0.0405 (4)
H30.27230.78691.10940.049*
C40.4201 (2)0.80982 (13)1.17718 (13)0.0441 (5)
H40.39920.77501.22540.053*
C50.52717 (18)0.85476 (12)1.17589 (11)0.0383 (4)
H50.57800.85161.22400.046*
C60.55930 (16)0.90460 (11)1.10322 (11)0.0327 (3)
C70.67683 (17)0.95101 (13)1.10201 (12)0.0391 (4)
H7A0.74090.90761.09740.047*
H7B0.68790.98541.15540.047*
C80.29202 (16)0.87651 (14)0.96090 (12)0.0382 (4)
H8A0.23450.92360.97270.046*
H8B0.24940.82080.95080.046*
C90.41665 (16)0.79598 (10)0.81364 (12)0.0339 (3)
C100.5097 (2)0.80785 (14)0.74313 (14)0.0488 (5)
H10A0.57840.83710.76740.073*
H10B0.47760.84390.69660.073*
H10C0.53220.75010.72050.073*
C110.3068 (2)0.75117 (14)0.77561 (15)0.0497 (5)
H11A0.27760.78610.72730.075*
H11B0.24630.74710.81990.075*
H11C0.32710.69200.75560.075*
C120.4694 (2)0.73571 (12)0.88360 (14)0.0471 (5)
H12A0.49340.67980.85770.071*
H12B0.41080.72450.92810.071*
H12C0.53740.76460.90930.071*
C130.28236 (17)0.97553 (14)0.79810 (13)0.0422 (4)
C140.15386 (19)0.94355 (18)0.79892 (18)0.0618 (6)
H14A0.10570.98400.76510.093*
H14B0.12520.94200.85820.093*
H14C0.14940.88440.77400.093*
C150.3241 (2)0.98364 (15)0.70379 (13)0.0539 (5)
H15A0.31620.92660.67510.081*
H15B0.40611.00200.70280.081*
H15C0.27641.02750.67380.081*
C160.2868 (3)1.06881 (15)0.83988 (18)0.0642 (7)
H16A0.23281.10810.80980.096*
H16B0.36631.09230.83570.096*
H16C0.26431.06460.90040.096*
C170.83287 (16)1.01907 (13)0.96814 (12)0.0369 (4)
C180.84152 (19)0.92899 (15)0.92080 (17)0.0524 (5)
H18A0.92170.92000.90070.079*
H18B0.78820.92880.87160.079*
H18C0.82010.88150.96040.079*
C190.92396 (18)1.02033 (17)1.04173 (15)0.0514 (5)
H19A1.00201.01031.01800.077*
H19B0.90550.97391.08320.077*
H19C0.92191.07761.07050.077*
C200.63680 (18)1.13804 (12)1.04915 (13)0.0403 (4)
C210.5238 (2)1.12685 (15)1.10274 (17)0.0593 (6)
H21A0.54011.09011.15300.089*
H21B0.46361.09871.06740.089*
H21C0.49621.18471.12170.089*
C220.7314 (2)1.17943 (16)1.10738 (16)0.0585 (6)
H22A0.80201.19071.07350.088*
H22B0.75001.13891.15430.088*
H22C0.70231.23491.13120.088*
C230.6101 (3)1.19968 (14)0.97333 (16)0.0571 (6)
H23A0.57861.25530.99510.086*
H23B0.55271.17190.93540.086*
H23C0.68211.21110.94120.086*
C240.86278 (18)1.09373 (16)0.90427 (14)0.0491 (5)
H24A0.85971.15050.93400.074*
H24B0.80621.09360.85710.074*
H24C0.94141.08440.88120.074*
U11U22U33U12U13U23
Ni10.02964 (9)0.02516 (9)0.02389 (9)−0.00470 (8)−0.00320 (8)0.00305 (7)
Cl10.0605 (3)0.0569 (3)0.02997 (19)−0.0283 (3)−0.00855 (19)0.0151 (2)
P10.02591 (18)0.02588 (17)0.02911 (19)−0.00090 (15)−0.00127 (15)−0.00323 (15)
P20.03048 (18)0.02878 (18)0.02431 (17)−0.00396 (16)−0.00252 (14)0.00080 (16)
C10.0318 (8)0.0261 (6)0.0256 (7)−0.0007 (6)0.0043 (6)0.0008 (6)
C20.0343 (8)0.0312 (8)0.0321 (8)−0.0005 (7)0.0090 (7)−0.0036 (6)
C30.0416 (10)0.0390 (9)0.0411 (9)−0.0050 (8)0.0187 (8)−0.0025 (8)
C40.0579 (12)0.0399 (9)0.0345 (9)0.0028 (9)0.0192 (9)0.0076 (7)
C50.0465 (10)0.0410 (9)0.0273 (8)0.0087 (8)0.0051 (8)0.0062 (7)
C60.0394 (9)0.0319 (8)0.0268 (7)0.0021 (7)0.0030 (6)0.0027 (6)
C70.0393 (9)0.0472 (10)0.0309 (8)−0.0033 (8)−0.0079 (7)0.0094 (7)
C80.0301 (8)0.0469 (10)0.0377 (9)−0.0050 (7)0.0061 (7)−0.0095 (8)
C90.0396 (9)0.0247 (7)0.0375 (9)−0.0030 (6)0.0075 (7)−0.0057 (6)
C100.0569 (13)0.0432 (10)0.0465 (11)0.0010 (9)0.0210 (9)−0.0067 (8)
C110.0562 (12)0.0374 (10)0.0556 (12)−0.0123 (9)0.0036 (10)−0.0146 (9)
C120.0604 (12)0.0281 (8)0.0529 (11)0.0085 (9)0.0101 (11)0.0009 (7)
C130.0421 (9)0.0404 (9)0.0442 (10)0.0116 (8)−0.0140 (8)−0.0054 (9)
C140.0352 (10)0.0807 (17)0.0696 (15)0.0119 (10)−0.0166 (10)−0.0113 (13)
C150.0648 (14)0.0528 (12)0.0441 (11)0.0079 (11)−0.0195 (10)0.0053 (9)
C160.0812 (18)0.0433 (11)0.0682 (16)0.0299 (12)−0.0268 (14)−0.0098 (11)
C170.0303 (8)0.0426 (9)0.0378 (9)−0.0044 (7)−0.0011 (7)0.0008 (8)
C180.0414 (10)0.0530 (12)0.0627 (13)0.0072 (9)0.0048 (10)−0.0128 (11)
C190.0348 (9)0.0644 (13)0.0551 (12)−0.0068 (9)−0.0094 (9)0.0041 (11)
C200.0479 (11)0.0351 (9)0.0378 (9)−0.0036 (8)0.0014 (8)−0.0089 (7)
C210.0600 (14)0.0528 (12)0.0650 (14)0.0047 (11)0.0205 (12)−0.0166 (11)
C220.0662 (15)0.0557 (13)0.0535 (13)−0.0148 (11)−0.0036 (12)−0.0227 (11)
C230.0776 (17)0.0351 (10)0.0586 (14)0.0104 (11)−0.0019 (13)0.0007 (9)
C240.0399 (10)0.0612 (12)0.0462 (11)−0.0106 (9)0.0041 (8)0.0102 (10)
Ni1—C11.9239 (15)C13—C151.534 (3)
Ni1—P12.1921 (4)C13—C141.535 (3)
Ni1—P22.1978 (4)C13—C161.545 (3)
Ni1—Cl12.2317 (5)C14—H14A0.9700
P1—C81.8308 (19)C14—H14B0.9700
P1—C91.8720 (16)C14—H14C0.9700
P1—C131.8763 (18)C15—H15A0.9700
P2—C71.8341 (18)C15—H15B0.9700
P2—C171.8746 (19)C15—H15C0.9700
P2—C201.8756 (19)C16—H16A0.9700
C1—C61.399 (2)C16—H16B0.9700
C1—C21.412 (2)C16—H16C0.9700
C2—C31.391 (2)C17—C241.532 (3)
C2—C81.502 (3)C17—C191.534 (3)
C3—C41.366 (3)C17—C181.543 (3)
C3—H30.9400C18—H18A0.9700
C4—C51.390 (3)C18—H18B0.9700
C4—H40.9400C18—H18C0.9700
C5—C61.397 (2)C19—H19A0.9700
C5—H50.9400C19—H19B0.9700
C6—C71.505 (3)C19—H19C0.9700
C7—H7A0.9800C20—C231.523 (3)
C7—H7B0.9800C20—C221.532 (3)
C8—H8A0.9800C20—C211.534 (3)
C8—H8B0.9800C21—H21A0.9700
C9—C101.525 (3)C21—H21B0.9700
C9—C121.531 (3)C21—H21C0.9700
C9—C111.533 (3)C22—H22A0.9700
C10—H10A0.9700C22—H22B0.9700
C10—H10B0.9700C22—H22C0.9700
C10—H10C0.9700C23—H23A0.9700
C11—H11A0.9700C23—H23B0.9700
C11—H11B0.9700C23—H23C0.9700
C11—H11C0.9700C24—H24A0.9700
C12—H12A0.9700C24—H24B0.9700
C12—H12B0.9700C24—H24C0.9700
C12—H12C0.9700
C1—Ni1—P185.08 (5)C15—C13—C14109.01 (18)
C1—Ni1—P284.83 (5)C15—C13—C16108.2 (2)
P1—Ni1—P2169.651 (18)C14—C13—C16108.22 (19)
C1—Ni1—Cl1176.13 (5)C15—C13—P1113.01 (14)
P1—Ni1—Cl194.109 (18)C14—C13—P1113.03 (17)
P2—Ni1—Cl196.109 (17)C16—C13—P1105.07 (13)
C8—P1—C9104.92 (9)C13—C14—H14A109.5
C8—P1—C13103.98 (9)C13—C14—H14B109.5
C9—P1—C13112.16 (9)H14A—C14—H14B109.5
C8—P1—Ni1102.50 (6)C13—C14—H14C109.5
C9—P1—Ni1113.34 (6)H14A—C14—H14C109.5
C13—P1—Ni1118.02 (7)H14B—C14—H14C109.5
C7—P2—C17103.12 (9)C13—C15—H15A109.5
C7—P2—C20106.10 (9)C13—C15—H15B109.5
C17—P2—C20112.36 (9)H15A—C15—H15B109.5
C7—P2—Ni1102.87 (6)C13—C15—H15C109.5
C17—P2—Ni1118.68 (6)H15A—C15—H15C109.5
C20—P2—Ni1111.98 (7)H15B—C15—H15C109.5
C6—C1—C2116.79 (15)C13—C16—H16A109.5
C6—C1—Ni1121.59 (12)C13—C16—H16B109.5
C2—C1—Ni1121.51 (12)H16A—C16—H16B109.5
C3—C2—C1121.26 (17)C13—C16—H16C109.5
C3—C2—C8120.69 (17)H16A—C16—H16C109.5
C1—C2—C8118.05 (15)H16B—C16—H16C109.5
C4—C3—C2120.70 (18)C24—C17—C19108.50 (16)
C4—C3—H3119.6C24—C17—C18109.02 (17)
C2—C3—H3119.6C19—C17—C18108.54 (18)
C3—C4—C5119.69 (17)C24—C17—P2112.50 (14)
C3—C4—H4120.2C19—C17—P2113.40 (13)
C5—C4—H4120.2C18—C17—P2104.70 (13)
C4—C5—C6120.04 (18)C17—C18—H18A109.5
C4—C5—H5120.0C17—C18—H18B109.5
C6—C5—H5120.0H18A—C18—H18B109.5
C5—C6—C1121.42 (16)C17—C18—H18C109.5
C5—C6—C7119.36 (17)H18A—C18—H18C109.5
C1—C6—C7119.21 (14)H18B—C18—H18C109.5
C6—C7—P2106.84 (12)C17—C19—H19A109.5
C6—C7—H7A110.4C17—C19—H19B109.5
P2—C7—H7A110.4H19A—C19—H19B109.5
C6—C7—H7B110.4C17—C19—H19C109.5
P2—C7—H7B110.4H19A—C19—H19C109.5
H7A—C7—H7B108.6H19B—C19—H19C109.5
C2—C8—P1106.23 (12)C23—C20—C22109.96 (19)
C2—C8—H8A110.5C23—C20—C21108.3 (2)
P1—C8—H8A110.5C22—C20—C21108.32 (18)
C2—C8—H8B110.5C23—C20—P2109.70 (13)
P1—C8—H8B110.5C22—C20—P2113.70 (16)
H8A—C8—H8B108.7C21—C20—P2106.63 (13)
C10—C9—C12107.52 (16)C20—C21—H21A109.5
C10—C9—C11109.93 (16)C20—C21—H21B109.5
C12—C9—C11109.06 (16)H21A—C21—H21B109.5
C10—C9—P1110.57 (12)C20—C21—H21C109.5
C12—C9—P1107.09 (12)H21A—C21—H21C109.5
C11—C9—P1112.49 (13)H21B—C21—H21C109.5
C9—C10—H10A109.5C20—C22—H22A109.5
C9—C10—H10B109.5C20—C22—H22B109.5
H10A—C10—H10B109.5H22A—C22—H22B109.5
C9—C10—H10C109.5C20—C22—H22C109.5
H10A—C10—H10C109.5H22A—C22—H22C109.5
H10B—C10—H10C109.5H22B—C22—H22C109.5
C9—C11—H11A109.5C20—C23—H23A109.5
C9—C11—H11B109.5C20—C23—H23B109.5
H11A—C11—H11B109.5H23A—C23—H23B109.5
C9—C11—H11C109.5C20—C23—H23C109.5
H11A—C11—H11C109.5H23A—C23—H23C109.5
H11B—C11—H11C109.5H23B—C23—H23C109.5
C9—C12—H12A109.5C17—C24—H24A109.5
C9—C12—H12B109.5C17—C24—H24B109.5
H12A—C12—H12B109.5H24A—C24—H24B109.5
C9—C12—H12C109.5C17—C24—H24C109.5
H12A—C12—H12C109.5H24A—C24—H24C109.5
H12B—C12—H12C109.5H24B—C24—H24C109.5
  3 in total

1.  Mechanism of direct molecular oxygen insertion in a palladium(II)-hydride bond.

Authors:  Jason M Keith; Richard P Muller; Richard A Kemp; Karen I Goldberg; William A Goddard; Jonas Oxgaard
Journal:  Inorg Chem       Date:  2006-11-27       Impact factor: 5.165

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Insertion of molecular oxygen into a palladium(II) hydride bond.

Authors:  Melanie C Denney; Nicole A Smythe; Kara L Cetto; Richard A Kemp; Karen I Goldberg
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419
  3 in total
  2 in total

1.  [2,6-Bis(di-tert-butyl-phosphinometh-yl)-phen-yl-κP,C,P'](nitrato-κO)nickel(II).

Authors:  Brian J Boro; Diane A Dickie; Eileen N Duesler; Karen I Goldberg; Richard A Kemp
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-10-15

2.  Bis{bis-[2-(diisopropyl-phosphan-yl)phen-yl]phosphanido-κ(3) P,P',P''}chloridonickel(II).

Authors:  Consiglia Tedesco; Marina Lamberti; Mina Mazzeo
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-11-07
  2 in total

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