Related literature {#sec1}
==================

For the synthesis, see: Soolinger *et al.* (1990[@bb11]). For analogues and related applications, see: Rosen *et al.* (2011[@bb9]); Zim *et al.* (2001[@bb13]); Chen & Yang (2007*a* [@bb3],*b* [@bb4]); Gao & Yang (2008[@bb6]); Zhou *et al.* (2009[@bb12]); Roma *et al.* (2011[@bb8]); Liu *et al.* (2008[@bb7]).

Experimental {#sec2}
============

 {#sec2.1}

### Crystal data {#sec2.1.1}

\[Ni(C~14~H~9~)Cl(C~18~H~15~P)~2~\]*M* *~r~* = 795.91Orthorhombic,*a* = 11.090 (5) Å*b* = 15.204 (7) Å*c* = 23.679 (10) Å*V* = 3993 (3) Å^3^*Z* = 4Mo *K*α radiationμ = 0.67 mm^−1^*T* = 110 K0.59 × 0.46 × 0.23 mm

### Data collection {#sec2.1.2}

Bruker APEXII CCD diffractometerAbsorption correction: multi-scan (*SADABS*; Bruker, 2008[@bb2]) *T* ~min~ = 0.692, *T* ~max~ = 0.86353371 measured reflections6780 independent reflections6359 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.048

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.024*wR*(*F* ^2^) = 0.057*S* = 1.026780 reflections488 parametersH-atom parameters constrainedΔρ~max~ = 0.26 e Å^−3^Δρ~min~ = −0.14 e Å^−3^Absolute structure: Flack (1983[@bb5]), 2986 Friedel pairsFlack parameter: 0.000 (7)

 {#d5e383}

Data collection: *APEX2* (Bruker, 2004[@bb1]); cell refinement: *SAINT* (Bruker, 2004[@bb1]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb10]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb10]); molecular graphics: *SHELXTL* (Sheldrick, 2008[@bb10]); software used to prepare material for publication: *SHELXTL*.

Supplementary Material
======================

Crystal structure: contains datablock(s) I, global. DOI: [10.1107/S1600536811032326/vm2114sup1.cif](http://dx.doi.org/10.1107/S1600536811032326/vm2114sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536811032326/vm2114Isup2.hkl](http://dx.doi.org/10.1107/S1600536811032326/vm2114Isup2.hkl)

Supplementary material file. DOI: [10.1107/S1600536811032326/vm2114Isup3.cdx](http://dx.doi.org/10.1107/S1600536811032326/vm2114Isup3.cdx)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?vm2114&file=vm2114sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?vm2114sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?vm2114&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [VM2114](http://scripts.iucr.org/cgi-bin/sendsup?vm2114)).

We thank the Welch Foundation (V-004) for financial support. We are very grateful to Dr Joseph Reibenspies at Texas A & M University for the X-ray crystallographic analysis. The X-ray diffractometers, small angle scattering instrumentation and crystallographic computing systems in the X-ray Diffraction Laboratory at the Department of Chemistry, Texas A & M University, were purchased with funds provided by the National Science Foundation (CHE-9807975, CHE-0079822 and CHE-0215838).

Comment
=======

Ni catalysts have attracted considerate attention in recent years. In comparison with Pd and Pt catalysts, Ni catalysts are more desirable from the standpoints of economics and versatility (Rosen *et al.*, 2011). Ni-catalyzed cross-coupling reactions play an important role in the formation of carbon-carbon and carbon-heteroatom bonds. The mechanism of Ni-catalyzed cross-coupling reactions was considered similar to the Pd-catalyzed cross-couplings (Rosen *et al.*, 2011). The catalytic cycle in both cases involves three sequential steps: oxidative addition, translation, and reductive elimination (Zim *et al.*, 2001). Ni(II) σ-aryl complex is believed to be the oxidative addition product in the Ni-catalyzed cross-coupling reactions. Soolinger *et al.* (1990), Chen & Yang (2007*a*,*b*), and Gao & Yang (2008) have demonstrated that isolatable Ni(II) σ-aryl complexes can be directly used as efficient catalysts for cross-coupling reactions. In addition, Zhou *et al.* (2009) have reported that Ni(II) σ-aryl complexes can catalyze dehalogenation of aryl chlorides, and Roma *et al.* (2011)have shown that Ni(II) σ-aryl complexes can promote the polymerization of methylmethacrylate.

As further advances in Ni(II) σ-aryl complexes as catalyst are necessary, we synthesized the title compound in an analogous fashion to the literature procedure (Soolinger *et al.*, 1990). The title compound is air- and thermally stable. The bond angles around Ni of the complex indicate that it exists in a slightly distorted square-planar geometry, which is similar to the geometry of its 1-naphthyl (Zhou *et al.*, 2009) and 4-acetylnaphthyl (Liu *et al.*, 2008) analogues. It is noteworthy that there are potentially C---H···Cl hydrogen bond intramolecular interactions, and the donor-acceptor distances are 2.862 Å for C22---H22A···Cl1 and 2.887 Å for C44---H44A···Cl1. There are also potentially C---H···Cl intermolecular interactions, and the donor-acceptor distances are 2.747 Å for C23---H23A···Cl1^i^ and 2.872 Å for C43---H43A···Cl1^i^ (symmetry codes: (i) -1/2 + *x*, 3/2 - *y*, - *z*). Intramolecular C---H···π interactions are observed as the distances from C32---H32A and C33---H33A to the centroid of the plane C1---C2---C3---C8---C9---C14 of the phenanthrene ring are 2.788 and 2.588 Å, respectively. The application of the title compound as catalyst in cross-coupling reactions is under investigation.

Experimental {#experimental}
============

A stirred mixture of 1.20 g (5.0 mmol) of NiCl~2~.6H~2~O, 2.88 g (11.0 mmol) of triphenylphosphine and 25 ml of 96% ethanol was heated until a gentle reflux started. 9-Chlorophenanthrene (10.0 mmol, 2.13 g, excess) was then added, followed by zinc dust (0.33 g, 5.0 mmol, Merck, analytical grade) over 5 min. The dark-green mixture very soon turned yellow. After stirring and heating under reflux for 1.5 h (under nitrogen), the mixture was cooled to 293 K. Four 2 ml portions of 30% aqueous hydrochloric acid were added over 15 min. After stirring for 1.5 h, the solid was filtered off on a sintered-glass funnel and successively washed with 5 ml of ethanol, twice with 5 ml of 1 *M* aqueous hydrochloric acid, twice with 5 ml of 96% ethanol and once with 5 ml of pentane. The yellowish solid (3.10 g) was dried *in vacuo*. Single crystals suitable for X-ray diffraction were obtained by recrystallization from CH~2~Cl~2~/hexanes.

Refinement {#refinement}
==========

All non-hydrogen atoms were refined with anisotropic thermal parameters. The hydrogen atoms bound to carbon atoms were placed in idealized positions and constrained to ride on their parent atoms, with d(C--H) = 0.95 Å, *U*~iso~(H) = 1.2*U*~eq~(C).

Figures
=======

![A view of the molecular structure. Ellipsoids are drawn at the 30% probability level.](e-67-m1272-fig1){#Fap1}

Crystal data {#tablewrapcrystaldatalong}
============

  ------------------------------------- ---------------------------------------
  \[Ni(C~14~H~9~)Cl(C~18~H~15~P)~2~\]   *F*(000) = 1656
  *M~r~* = 795.91                       *D*~x~ = 1.324 Mg m^−3^
  Orthorhombic, *P*2~1~2~1~2~1~         Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: P 2ac 2ab                Cell parameters from 6845 reflections
  *a* = 11.090 (5) Å                    θ = 2.2--26.7°
  *b* = 15.204 (7) Å                    µ = 0.67 mm^−1^
  *c* = 23.679 (10) Å                   *T* = 110 K
  *V* = 3993 (3) Å^3^                   Plate, orange
  *Z* = 4                               0.59 × 0.46 × 0.23 mm
  ------------------------------------- ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  ------------------------------------------------------------ --------------------------------------
  Bruker APEXII CCD diffractometer                             6780 independent reflections
  Radiation source: fine-focus sealed tube                     6359 reflections with *I* \> 2σ(*I*)
  graphite                                                     *R*~int~ = 0.048
  φ and ω scans                                                θ~max~ = 25.0°, θ~min~ = 2.0°
  Absorption correction: multi-scan (*SADABS*; Bruker, 2008)   *h* = −13→13
  *T*~min~ = 0.692, *T*~max~ = 0.863                           *k* = −18→18
  53371 measured reflections                                   *l* = −28→28
  ------------------------------------------------------------ --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ---------------------------------------------------------------- -------------------------------------------------------------------------------------
  Refinement on *F*^2^                                             Secondary atom site location: difference Fourier map
  Least-squares matrix: full                                       Hydrogen site location: inferred from neighbouring sites
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.024                              H-atom parameters constrained
  *wR*(*F*^2^) = 0.057                                             *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0354*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  *S* = 1.02                                                       (Δ/σ)~max~ = 0.002
  6780 reflections                                                 Δρ~max~ = 0.26 e Å^−3^
  488 parameters                                                   Δρ~min~ = −0.14 e Å^−3^
  0 restraints                                                     Absolute structure: Flack (1983), 2986 Friedel pairs
  Primary atom site location: structure-invariant direct methods   Flack parameter: 0.000 (7)
  ---------------------------------------------------------------- -------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  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 *F*^2^ against ALL reflections. The weighted *R*-factor *wR* and goodness of fit *S* are based on *F*^2^, conventional *R*-factors *R* are based on *F*, with *F* set to zero for negative *F*^2^. The threshold expression of *F*^2^ \> σ(*F*^2^) is used only for calculating *R*-factors(gt) *etc.* and is not relevant to the choice of reflections for refinement. *R*-factors based on *F*^2^ 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 (Å^2^) {#tablewrapcoords}
==================================================================================================

  ------ -------------- --------------- ---------------- -------------------- --
         *x*            *y*             *z*              *U*~iso~\*/*U*~eq~   
  Ni1    0.56721 (2)    0.527489 (15)   −0.047248 (9)    0.02000 (7)          
  Cl1    0.49242 (4)    0.63193 (3)     0.009025 (18)    0.02449 (11)         
  P1     0.65475 (5)    0.45655 (3)     0.024960 (19)    0.02055 (11)         
  P2     0.50725 (4)    0.59607 (3)     −0.125640 (19)   0.02011 (11)         
  C1     0.65053 (18)   0.44916 (12)    −0.09623 (8)     0.0215 (4)           
  C2     0.76625 (18)   0.46946 (15)    −0.11185 (8)     0.0264 (4)           
  H2A    0.8004         0.5235          −0.0997          0.032\*              
  C3     0.83753 (19)   0.41080 (15)    −0.14631 (8)     0.0285 (5)           
  C4     0.95831 (19)   0.43137 (16)    −0.15978 (10)    0.0373 (6)           
  H4A    0.9910         0.4862          −0.1482          0.045\*              
  C5     1.0289 (2)     0.37379 (18)    −0.18910 (11)    0.0481 (7)           
  H5A    1.1103         0.3884          −0.1974          0.058\*              
  C6     0.9811 (3)     0.29272 (18)    −0.20702 (11)    0.0503 (7)           
  H6A    1.0305         0.2524          −0.2272          0.060\*              
  C7     0.8645 (2)     0.27199 (17)    −0.19557 (9)     0.0409 (6)           
  H7A    0.8331         0.2174          −0.2083          0.049\*              
  C8     0.7884 (2)     0.33008 (14)    −0.16497 (9)     0.0298 (5)           
  C9     0.66463 (19)   0.30797 (14)    −0.15135 (8)     0.0272 (5)           
  C10    0.6079 (2)     0.23092 (15)    −0.16979 (9)     0.0355 (5)           
  H10A   0.6516         0.1905          −0.1925          0.043\*              
  C11    0.4903 (2)     0.21231 (15)    −0.15580 (9)     0.0387 (6)           
  H11A   0.4536         0.1598          −0.1691          0.046\*              
  C12    0.4251 (2)     0.26995 (14)    −0.12229 (9)     0.0343 (5)           
  H12A   0.3441         0.2567          −0.1124          0.041\*              
  C13    0.47822 (19)   0.34736 (14)    −0.10304 (8)     0.0292 (5)           
  H13A   0.4328         0.3866          −0.0802          0.035\*              
  C14    0.59785 (18)   0.36821 (13)    −0.11689 (8)     0.0242 (4)           
  C15    0.36705 (18)   0.65927 (14)    −0.12249 (8)     0.0253 (4)           
  C16    0.2761 (2)     0.63172 (17)    −0.08626 (9)     0.0359 (5)           
  H16A   0.2892         0.5835          −0.0615          0.043\*              
  C17    0.1658 (2)     0.67511 (19)    −0.08639 (10)    0.0473 (7)           
  H17A   0.1035         0.6565          −0.0616          0.057\*              
  C18    0.1462 (2)     0.74547 (18)    −0.12253 (10)    0.0451 (6)           
  H18A   0.0710         0.7753          −0.1221          0.054\*              
  C19    0.2356 (2)     0.77222 (16)    −0.15896 (10)    0.0379 (6)           
  H19A   0.2215         0.8199          −0.1840          0.046\*              
  C20    0.34575 (19)   0.72989 (14)    −0.15910 (9)     0.0286 (5)           
  H20A   0.4074         0.7488          −0.1842          0.034\*              
  C21    0.62413 (17)   0.67544 (13)    −0.14485 (8)     0.0230 (4)           
  C22    0.69398 (18)   0.71257 (14)    −0.10193 (9)     0.0259 (5)           
  H22A   0.6773         0.6984          −0.0637          0.031\*              
  C23    0.7876 (2)     0.77001 (15)    −0.11455 (9)     0.0315 (5)           
  H23A   0.8341         0.7953          −0.0850          0.038\*              
  C24    0.81292 (19)   0.79046 (15)    −0.17089 (9)     0.0318 (5)           
  H24A   0.8782         0.8285          −0.1797          0.038\*              
  C25    0.74276 (19)   0.75518 (14)    −0.21397 (10)    0.0331 (5)           
  H25A   0.7591         0.7699          −0.2522          0.040\*              
  C26    0.64865 (19)   0.69838 (14)    −0.20099 (8)     0.0265 (5)           
  H26A   0.6004         0.6748          −0.2305          0.032\*              
  C27    0.48354 (17)   0.53297 (13)    −0.19152 (7)     0.0222 (4)           
  C28    0.36738 (19)   0.51242 (14)    −0.20905 (8)     0.0278 (5)           
  H28A   0.3002         0.5325          −0.1878          0.033\*              
  C29    0.3486 (2)     0.46246 (15)    −0.25774 (9)     0.0349 (5)           
  H29A   0.2687         0.4483          −0.2690          0.042\*              
  C30    0.4445 (2)     0.43348 (15)    −0.28973 (9)     0.0353 (5)           
  H30A   0.4310         0.4001          −0.3231          0.042\*              
  C31    0.5605 (2)     0.45350 (14)    −0.27274 (8)     0.0312 (5)           
  H31A   0.6272         0.4337          −0.2945          0.037\*              
  C32    0.58031 (19)   0.50237 (13)    −0.22399 (8)     0.0258 (4)           
  H32A   0.6605         0.5152          −0.2126          0.031\*              
  C33    0.76549 (19)   0.30173 (14)    −0.01596 (8)     0.0267 (5)           
  H33A   0.8154         0.3402          −0.0372          0.032\*              
  C34    0.7797 (2)     0.21147 (14)    −0.02159 (9)     0.0294 (5)           
  H34A   0.8389         0.1888          −0.0467          0.035\*              
  C35    0.7080 (2)     0.15427 (15)    0.00917 (9)      0.0336 (5)           
  H35A   0.7178         0.0925          0.0052           0.040\*              
  C36    0.6218 (2)     0.18761 (14)    0.04567 (11)     0.0357 (5)           
  H36A   0.5718         0.1486          0.0666           0.043\*              
  C37    0.60811 (18)   0.27826 (13)    0.05175 (9)      0.0296 (5)           
  H37A   0.5499         0.3006          0.0775           0.036\*              
  C38    0.67883 (17)   0.33683 (13)    0.02052 (8)      0.0222 (4)           
  C39    0.80445 (17)   0.50331 (13)    0.03660 (7)      0.0223 (4)           
  C40    0.90278 (18)   0.45309 (13)    0.05382 (8)      0.0275 (5)           
  H40A   0.8941         0.3915          0.0591           0.033\*              
  C41    1.0134 (2)     0.49305 (15)    0.06328 (9)      0.0315 (5)           
  H41A   1.0800         0.4588          0.0756           0.038\*              
  C42    1.02723 (19)   0.58275 (15)    0.05485 (9)      0.0325 (5)           
  H42A   1.1038         0.6094          0.0604           0.039\*              
  C43    0.9301 (2)     0.63360 (13)    0.03836 (8)      0.0320 (5)           
  H43A   0.9395         0.6951          0.0329           0.038\*              
  C44    0.81898 (18)   0.59436 (14)    0.02980 (8)      0.0265 (4)           
  H44A   0.7518         0.6295          0.0192           0.032\*              
  C45    0.58119 (18)   0.46590 (13)    0.09426 (7)      0.0235 (4)           
  C46    0.6465 (2)     0.46476 (15)    0.14471 (8)      0.0316 (5)           
  H46A   0.7321         0.4650          0.1435           0.038\*              
  C47    0.5875 (2)     0.46324 (17)    0.19689 (8)      0.0380 (5)           
  H47A   0.6328         0.4635          0.2310           0.046\*              
  C48    0.4638 (2)     0.46144 (15)    0.19862 (8)      0.0345 (5)           
  H48A   0.4233         0.4591          0.2339           0.041\*              
  C49    0.3976 (2)     0.46299 (15)    0.14867 (9)      0.0311 (5)           
  H49A   0.3120         0.4622          0.1500           0.037\*              
  C50    0.45626 (18)   0.46568 (14)    0.09676 (8)      0.0264 (4)           
  H50A   0.4105         0.4674          0.0629           0.032\*              
  ------ -------------- --------------- ---------------- -------------------- --

Atomic displacement parameters (Å^2^) {#tablewrapadps}
=====================================

  ----- -------------- -------------- -------------- -------------- -------------- ---------------
        *U*^11^        *U*^22^        *U*^33^        *U*^12^        *U*^13^        *U*^23^
  Ni1   0.02228 (12)   0.01963 (13)   0.01808 (11)   0.00345 (10)   0.00132 (10)   −0.00025 (10)
  Cl1   0.0339 (3)     0.0210 (2)     0.0185 (2)     0.0106 (2)     0.00216 (19)   −0.00120 (17)
  P1    0.0232 (2)     0.0196 (3)     0.0189 (2)     0.0014 (2)     0.00066 (19)   0.00014 (19)
  P2    0.0200 (2)     0.0211 (3)     0.0192 (2)     0.0012 (2)     −0.0001 (2)    0.00030 (19)
  C1    0.0253 (10)    0.0201 (11)    0.0192 (9)     0.0044 (8)     −0.0008 (8)    0.0023 (8)
  C2    0.0291 (11)    0.0271 (11)    0.0230 (10)    0.0051 (10)    0.0002 (8)     0.0050 (9)
  C3    0.0296 (11)    0.0336 (12)    0.0224 (10)    0.0084 (10)    0.0051 (9)     0.0095 (9)
  C4    0.0291 (12)    0.0431 (14)    0.0397 (12)    0.0084 (10)    0.0064 (10)    0.0168 (11)
  C5    0.0366 (14)    0.0590 (18)    0.0486 (14)    0.0147 (12)    0.0174 (11)    0.0199 (13)
  C6    0.0603 (17)    0.0449 (16)    0.0458 (14)    0.0219 (14)    0.0245 (13)    0.0119 (12)
  C7    0.0564 (17)    0.0369 (14)    0.0294 (12)    0.0162 (12)    0.0137 (11)    0.0041 (10)
  C8    0.0387 (12)    0.0292 (12)    0.0214 (10)    0.0093 (10)    0.0030 (9)     0.0065 (9)
  C9    0.0369 (12)    0.0262 (11)    0.0186 (10)    0.0055 (10)    0.0016 (9)     0.0051 (8)
  C10   0.0581 (16)    0.0252 (12)    0.0231 (11)    0.0030 (11)    0.0017 (10)    −0.0013 (9)
  C11   0.0580 (16)    0.0295 (12)    0.0286 (11)    −0.0104 (12)   −0.0067 (11)   0.0028 (9)
  C12   0.0386 (13)    0.0324 (12)    0.0317 (11)    −0.0112 (11)   −0.0052 (10)   0.0069 (10)
  C13   0.0368 (12)    0.0267 (11)    0.0242 (10)    0.0001 (9)     0.0009 (9)     0.0027 (8)
  C14   0.0317 (11)    0.0206 (10)    0.0204 (9)     0.0016 (9)     −0.0016 (8)    0.0041 (8)
  C15   0.0226 (10)    0.0305 (12)    0.0229 (10)    0.0022 (9)     −0.0035 (8)    −0.0069 (9)
  C16   0.0275 (12)    0.0529 (15)    0.0273 (11)    0.0050 (11)    0.0031 (9)     0.0064 (10)
  C17   0.0261 (12)    0.081 (2)      0.0345 (12)    0.0106 (13)    0.0081 (10)    0.0030 (13)
  C18   0.0279 (13)    0.0627 (18)    0.0446 (14)    0.0183 (12)    −0.0054 (11)   −0.0085 (13)
  C19   0.0352 (13)    0.0349 (13)    0.0437 (14)    0.0099 (11)    −0.0099 (11)   −0.0031 (11)
  C20   0.0248 (11)    0.0279 (12)    0.0330 (11)    0.0030 (9)     −0.0052 (9)    −0.0019 (9)
  C21   0.0202 (10)    0.0205 (11)    0.0285 (10)    0.0029 (8)     −0.0024 (8)    0.0030 (8)
  C22   0.0271 (11)    0.0264 (11)    0.0241 (10)    0.0014 (9)     −0.0014 (9)    0.0011 (8)
  C23   0.0269 (11)    0.0310 (12)    0.0365 (12)    −0.0009 (10)   −0.0075 (9)    −0.0010 (10)
  C24   0.0244 (11)    0.0301 (12)    0.0410 (13)    −0.0030 (9)    0.0033 (10)    0.0042 (10)
  C25   0.0323 (13)    0.0340 (13)    0.0329 (12)    −0.0025 (10)   0.0030 (10)    0.0056 (10)
  C26   0.0264 (11)    0.0278 (11)    0.0254 (10)    −0.0023 (9)    −0.0023 (9)    0.0032 (9)
  C27   0.0260 (10)    0.0198 (10)    0.0208 (8)     0.0011 (9)     −0.0009 (8)    0.0023 (8)
  C28   0.0267 (11)    0.0272 (12)    0.0295 (10)    0.0003 (9)     −0.0012 (9)    −0.0008 (9)
  C29   0.0354 (12)    0.0337 (12)    0.0357 (11)    −0.0023 (11)   −0.0091 (10)   −0.0031 (10)
  C30   0.0488 (14)    0.0311 (12)    0.0260 (10)    −0.0010 (11)   −0.0045 (11)   −0.0048 (9)
  C31   0.0388 (12)    0.0300 (12)    0.0248 (10)    0.0017 (11)    0.0091 (9)     −0.0002 (9)
  C32   0.0264 (11)    0.0277 (11)    0.0233 (9)     −0.0010 (9)    0.0018 (8)     0.0022 (8)
  C33   0.0302 (11)    0.0260 (11)    0.0238 (10)    0.0026 (9)     −0.0011 (9)    0.0026 (9)
  C34   0.0304 (12)    0.0271 (12)    0.0307 (11)    0.0062 (9)     −0.0043 (9)    −0.0030 (9)
  C35   0.0373 (12)    0.0212 (11)    0.0422 (13)    0.0002 (10)    −0.0084 (10)   0.0001 (10)
  C36   0.0327 (12)    0.0256 (12)    0.0488 (13)    −0.0056 (9)    −0.0014 (11)   0.0050 (11)
  C37   0.0251 (11)    0.0295 (12)    0.0342 (11)    0.0005 (9)     0.0020 (9)     0.0031 (10)
  C38   0.0234 (10)    0.0217 (10)    0.0216 (9)     0.0006 (8)     −0.0041 (8)    −0.0004 (8)
  C39   0.0251 (10)    0.0239 (10)    0.0180 (9)     −0.0004 (8)    0.0021 (8)     0.0001 (8)
  C40   0.0306 (11)    0.0215 (11)    0.0305 (10)    −0.0008 (8)    −0.0020 (9)    −0.0001 (9)
  C41   0.0260 (11)    0.0343 (12)    0.0344 (11)    0.0020 (10)    −0.0017 (9)    −0.0033 (9)
  C42   0.0324 (12)    0.0362 (13)    0.0288 (11)    −0.0099 (10)   0.0028 (9)     −0.0061 (9)
  C43   0.0435 (12)    0.0238 (11)    0.0285 (11)    −0.0071 (10)   0.0022 (10)    0.0001 (9)
  C44   0.0312 (11)    0.0231 (10)    0.0252 (10)    −0.0010 (9)    0.0005 (8)     0.0024 (8)
  C45   0.0299 (11)    0.0189 (10)    0.0217 (9)     −0.0011 (9)    0.0025 (8)     −0.0011 (8)
  C46   0.0294 (11)    0.0398 (13)    0.0257 (10)    0.0010 (11)    −0.0010 (8)    −0.0010 (10)
  C47   0.0425 (14)    0.0489 (15)    0.0225 (10)    −0.0009 (12)   −0.0034 (9)    −0.0010 (10)
  C48   0.0449 (14)    0.0355 (13)    0.0232 (10)    −0.0007 (11)   0.0102 (9)     −0.0028 (9)
  C49   0.0320 (11)    0.0284 (12)    0.0331 (11)    −0.0021 (10)   0.0054 (9)     −0.0012 (10)
  C50   0.0288 (11)    0.0249 (10)    0.0255 (9)     −0.0017 (9)    −0.0015 (8)    −0.0001 (9)
  ----- -------------- -------------- -------------- -------------- -------------- ---------------

Geometric parameters (Å, °) {#tablewrapgeomlong}
===========================

  ----------------------- -------------- ----------------------- --------------
  Ni1---C1                1.9020 (19)    C23---H23A              0.9500
  Ni1---P2                2.2305 (9)     C24---C25               1.391 (3)
  Ni1---Cl1               2.2327 (8)     C24---H24A              0.9500
  Ni1---P1                2.2426 (8)     C25---C26               1.389 (3)
  P1---C39                1.827 (2)      C25---H25A              0.9500
  P1---C45                1.8381 (19)    C26---H26A              0.9500
  P1---C38                1.843 (2)      C27---C28               1.389 (3)
  P2---C21                1.829 (2)      C27---C32               1.400 (3)
  P2---C15                1.829 (2)      C28---C29               1.396 (3)
  P2---C27                1.850 (2)      C28---H28A              0.9500
  C1---C2                 1.371 (3)      C29---C30               1.378 (3)
  C1---C14                1.448 (3)      C29---H29A              0.9500
  C2---C3                 1.444 (3)      C30---C31               1.383 (3)
  C2---H2A                0.9500         C30---H30A              0.9500
  C3---C4                 1.412 (3)      C31---C32               1.390 (3)
  C3---C8                 1.414 (3)      C31---H31A              0.9500
  C4---C5                 1.364 (3)      C32---H32A              0.9500
  C4---H4A                0.9500         C33---C34               1.388 (3)
  C5---C6                 1.407 (4)      C33---C38               1.398 (3)
  C5---H5A                0.9500         C33---H33A              0.9500
  C6---C7                 1.358 (4)      C34---C35               1.386 (3)
  C6---H6A                0.9500         C34---H34A              0.9500
  C7---C8                 1.420 (3)      C35---C36               1.385 (3)
  C7---H7A                0.9500         C35---H35A              0.9500
  C8---C9                 1.450 (3)      C36---C37               1.394 (3)
  C9---C10                1.400 (3)      C36---H36A              0.9500
  C9---C14                1.433 (3)      C37---C38               1.398 (3)
  C10---C11               1.375 (3)      C37---H37A              0.9500
  C10---H10A              0.9500         C39---C40               1.392 (3)
  C11---C12               1.386 (3)      C39---C44               1.403 (3)
  C11---H11A              0.9500         C40---C41               1.387 (3)
  C12---C13               1.393 (3)      C40---H40A              0.9500
  C12---H12A              0.9500         C41---C42               1.387 (3)
  C13---C14               1.403 (3)      C41---H41A              0.9500
  C13---H13A              0.9500         C42---C43               1.382 (3)
  C15---C16               1.389 (3)      C42---H42A              0.9500
  C15---C20               1.400 (3)      C43---C44               1.384 (3)
  C16---C17               1.390 (3)      C43---H43A              0.9500
  C16---H16A              0.9500         C44---H44A              0.9500
  C17---C18               1.387 (4)      C45---C50               1.387 (3)
  C17---H17A              0.9500         C45---C46               1.397 (3)
  C18---C19               1.375 (4)      C46---C47               1.398 (3)
  C18---H18A              0.9500         C46---H46A              0.9500
  C19---C20               1.381 (3)      C47---C48               1.373 (3)
  C19---H19A              0.9500         C47---H47A              0.9500
  C20---H20A              0.9500         C48---C49               1.392 (3)
  C21---C22               1.397 (3)      C48---H48A              0.9500
  C21---C26               1.401 (3)      C49---C50               1.391 (3)
  C22---C23               1.389 (3)      C49---H49A              0.9500
  C22---H22A              0.9500         C50---H50A              0.9500
  C23---C24               1.398 (3)                              
                                                                 
  C1---Ni1---P2           85.99 (6)      C22---C23---C24         119.7 (2)
  C1---Ni1---Cl1          171.79 (6)     C22---C23---H23A        120.2
  P2---Ni1---Cl1          93.06 (4)      C24---C23---H23A        120.2
  C1---Ni1---P1           87.33 (6)      C25---C24---C23         120.1 (2)
  P2---Ni1---P1           171.26 (2)     C25---C24---H24A        120.0
  Cl1---Ni1---P1          92.74 (3)      C23---C24---H24A        120.0
  C39---P1---C45          103.80 (9)     C26---C25---C24         119.9 (2)
  C39---P1---C38          105.14 (9)     C26---C25---H25A        120.1
  C45---P1---C38          101.05 (9)     C24---C25---H25A        120.1
  C39---P1---Ni1          108.74 (6)     C25---C26---C21         120.70 (19)
  C45---P1---Ni1          116.83 (7)     C25---C26---H26A        119.7
  C38---P1---Ni1          119.63 (6)     C21---C26---H26A        119.7
  C21---P2---C15          105.43 (10)    C28---C27---C32         118.18 (18)
  C21---P2---C27          103.49 (9)     C28---C27---P2          120.03 (15)
  C15---P2---C27          100.72 (9)     C32---C27---P2          121.77 (15)
  C21---P2---Ni1          107.71 (7)     C27---C28---C29         120.5 (2)
  C15---P2---Ni1          117.71 (7)     C27---C28---H28A        119.8
  C27---P2---Ni1          120.11 (7)     C29---C28---H28A        119.8
  C2---C1---C14           118.56 (18)    C30---C29---C28         120.9 (2)
  C2---C1---Ni1           118.58 (15)    C30---C29---H29A        119.6
  C14---C1---Ni1          122.85 (15)    C28---C29---H29A        119.6
  C1---C2---C3            121.7 (2)      C29---C30---C31         119.21 (19)
  C1---C2---H2A           119.1          C29---C30---H30A        120.4
  C3---C2---H2A           119.1          C31---C30---H30A        120.4
  C4---C3---C8            119.2 (2)      C30---C31---C32         120.4 (2)
  C4---C3---C2            120.7 (2)      C30---C31---H31A        119.8
  C8---C3---C2            120.11 (19)    C32---C31---H31A        119.8
  C5---C4---C3            121.2 (2)      C31---C32---C27         120.8 (2)
  C5---C4---H4A           119.4          C31---C32---H32A        119.6
  C3---C4---H4A           119.4          C27---C32---H32A        119.6
  C4---C5---C6            120.0 (2)      C34---C33---C38         121.0 (2)
  C4---C5---H5A           120.0          C34---C33---H33A        119.5
  C6---C5---H5A           120.0          C38---C33---H33A        119.5
  C7---C6---C5            120.1 (2)      C35---C34---C33         120.3 (2)
  C7---C6---H6A           119.9          C35---C34---H34A        119.8
  C5---C6---H6A           119.9          C33---C34---H34A        119.8
  C6---C7---C8            121.6 (3)      C36---C35---C34         119.7 (2)
  C6---C7---H7A           119.2          C36---C35---H35A        120.2
  C8---C7---H7A           119.2          C34---C35---H35A        120.2
  C3---C8---C7            118.1 (2)      C35---C36---C37         120.1 (2)
  C3---C8---C9            119.78 (19)    C35---C36---H36A        120.0
  C7---C8---C9            122.1 (2)      C37---C36---H36A        120.0
  C10---C9---C14          118.7 (2)      C36---C37---C38         120.9 (2)
  C10---C9---C8           123.4 (2)      C36---C37---H37A        119.5
  C14---C9---C8           117.90 (19)    C38---C37---H37A        119.5
  C11---C10---C9          121.6 (2)      C33---C38---C37         117.99 (19)
  C11---C10---H10A        119.2          C33---C38---P1          120.79 (15)
  C9---C10---H10A         119.2          C37---C38---P1          121.17 (15)
  C10---C11---C12         120.2 (2)      C40---C39---C44         119.01 (18)
  C10---C11---H11A        119.9          C40---C39---P1          122.85 (15)
  C12---C11---H11A        119.9          C44---C39---P1          118.10 (15)
  C11---C12---C13         120.1 (2)      C41---C40---C39         119.98 (19)
  C11---C12---H12A        120.0          C41---C40---H40A        120.0
  C13---C12---H12A        120.0          C39---C40---H40A        120.0
  C12---C13---C14         121.0 (2)      C42---C41---C40         120.4 (2)
  C12---C13---H13A        119.5          C42---C41---H41A        119.8
  C14---C13---H13A        119.5          C40---C41---H41A        119.8
  C13---C14---C9          118.52 (19)    C43---C42---C41         120.3 (2)
  C13---C14---C1          119.65 (18)    C43---C42---H42A        119.9
  C9---C14---C1           121.82 (18)    C41---C42---H42A        119.9
  C16---C15---C20         119.42 (19)    C42---C43---C44         119.61 (19)
  C16---C15---P2          118.96 (16)    C42---C43---H43A        120.2
  C20---C15---P2          121.39 (16)    C44---C43---H43A        120.2
  C15---C16---C17         119.7 (2)      C43---C44---C39         120.7 (2)
  C15---C16---H16A        120.2          C43---C44---H44A        119.6
  C17---C16---H16A        120.2          C39---C44---H44A        119.6
  C18---C17---C16         120.3 (2)      C50---C45---C46         118.78 (17)
  C18---C17---H17A        119.8          C50---C45---P1          118.76 (15)
  C16---C17---H17A        119.8          C46---C45---P1          122.17 (15)
  C19---C18---C17         120.2 (2)      C45---C46---C47         120.9 (2)
  C19---C18---H18A        119.9          C45---C46---H46A        119.6
  C17---C18---H18A        119.9          C47---C46---H46A        119.6
  C18---C19---C20         120.1 (2)      C48---C47---C46         119.60 (19)
  C18---C19---H19A        120.0          C48---C47---H47A        120.2
  C20---C19---H19A        120.0          C46---C47---H47A        120.2
  C19---C20---C15         120.3 (2)      C47---C48---C49         120.08 (18)
  C19---C20---H20A        119.8          C47---C48---H48A        120.0
  C15---C20---H20A        119.8          C49---C48---H48A        120.0
  C22---C21---C26         118.82 (19)    C50---C49---C48         120.31 (19)
  C22---C21---P2          118.61 (15)    C50---C49---H49A        119.8
  C26---C21---P2          122.54 (15)    C48---C49---H49A        119.8
  C23---C22---C21         120.79 (19)    C45---C50---C49         120.32 (19)
  C23---C22---H22A        119.6          C45---C50---H50A        119.8
  C21---C22---H22A        119.6          C49---C50---H50A        119.8
                                                                 
  C1---Ni1---P1---C39     84.48 (9)      P2---C15---C20---C19    174.90 (16)
  P2---Ni1---P1---C39     44.27 (16)     C15---P2---C21---C22    96.93 (17)
  Cl1---Ni1---P1---C39    −87.30 (7)     C27---P2---C21---C22    −157.73 (16)
  C1---Ni1---P1---C45     −158.52 (9)    Ni1---P2---C21---C22    −29.55 (17)
  P2---Ni1---P1---C45     161.27 (15)    C15---P2---C21---C26    −85.05 (18)
  Cl1---Ni1---P1---C45    29.69 (8)      C27---P2---C21---C26    20.30 (19)
  C1---Ni1---P1---C38     −36.20 (10)    Ni1---P2---C21---C26    148.47 (16)
  P2---Ni1---P1---C38     −76.41 (16)    C26---C21---C22---C23   −1.1 (3)
  Cl1---Ni1---P1---C38    152.02 (8)     P2---C21---C22---C23    176.97 (16)
  C1---Ni1---P2---C21     −86.28 (9)     C21---C22---C23---C24   −0.5 (3)
  Cl1---Ni1---P2---C21    85.55 (7)      C22---C23---C24---C25   1.7 (3)
  P1---Ni1---P2---C21     −46.01 (17)    C23---C24---C25---C26   −1.1 (3)
  C1---Ni1---P2---C15     154.82 (10)    C24---C25---C26---C21   −0.6 (3)
  Cl1---Ni1---P2---C15    −33.35 (8)     C22---C21---C26---C25   1.7 (3)
  P1---Ni1---P2---C15     −164.90 (15)   P2---C21---C26---C25    −176.32 (16)
  C1---Ni1---P2---C27     31.63 (10)     C21---P2---C27---C28    −136.92 (17)
  Cl1---Ni1---P2---C27    −156.53 (8)    C15---P2---C27---C28    −28.02 (19)
  P1---Ni1---P2---C27     71.91 (17)     Ni1---P2---C27---C28    103.04 (16)
  P2---Ni1---C1---C2      88.87 (15)     C21---P2---C27---C32    45.10 (18)
  Cl1---Ni1---C1---C2     5.2 (5)        C15---P2---C27---C32    154.00 (17)
  P1---Ni1---C1---C2      −85.49 (15)    Ni1---P2---C27---C32    −74.95 (17)
  P2---Ni1---C1---C14     −92.31 (15)    C32---C27---C28---C29   0.1 (3)
  Cl1---Ni1---C1---C14    −176.0 (3)     P2---C27---C28---C29    −177.97 (16)
  P1---Ni1---C1---C14     93.33 (15)     C27---C28---C29---C30   −0.8 (3)
  C14---C1---C2---C3      −2.4 (3)       C28---C29---C30---C31   0.8 (3)
  Ni1---C1---C2---C3      176.45 (14)    C29---C30---C31---C32   −0.1 (3)
  C1---C2---C3---C4       −177.19 (18)   C30---C31---C32---C27   −0.6 (3)
  C1---C2---C3---C8       0.1 (3)        C28---C27---C32---C31   0.6 (3)
  C8---C3---C4---C5       −1.7 (3)       P2---C27---C32---C31    178.65 (15)
  C2---C3---C4---C5       175.6 (2)      C38---C33---C34---C35   −0.2 (3)
  C3---C4---C5---C6       0.7 (4)        C33---C34---C35---C36   0.0 (3)
  C4---C5---C6---C7       0.5 (4)        C34---C35---C36---C37   −0.6 (3)
  C5---C6---C7---C8       −0.8 (4)       C35---C36---C37---C38   1.3 (3)
  C4---C3---C8---C7       1.4 (3)        C34---C33---C38---C37   0.9 (3)
  C2---C3---C8---C7       −175.90 (19)   C34---C33---C38---P1    −176.66 (16)
  C4---C3---C8---C9       179.86 (18)    C36---C37---C38---C33   −1.5 (3)
  C2---C3---C8---C9       2.5 (3)        C36---C37---C38---P1    176.07 (17)
  C6---C7---C8---C3       −0.2 (3)       C39---P1---C38---C33    −51.45 (17)
  C6---C7---C8---C9       −178.6 (2)     C45---P1---C38---C33    −159.19 (16)
  C3---C8---C9---C10      177.74 (19)    Ni1---P1---C38---C33    71.01 (17)
  C7---C8---C9---C10      −3.9 (3)       C39---P1---C38---C37    131.07 (17)
  C3---C8---C9---C14      −2.7 (3)       C45---P1---C38---C37    23.33 (18)
  C7---C8---C9---C14      175.66 (19)    Ni1---P1---C38---C37    −106.46 (16)
  C14---C9---C10---C11    0.3 (3)        C45---P1---C39---C40    89.94 (17)
  C8---C9---C10---C11     179.84 (19)    C38---P1---C39---C40    −15.78 (18)
  C9---C10---C11---C12    −0.6 (3)       Ni1---P1---C39---C40    −145.03 (15)
  C10---C11---C12---C13   0.5 (3)        C45---P1---C39---C44    −87.64 (16)
  C11---C12---C13---C14   −0.2 (3)       C38---P1---C39---C44    166.64 (15)
  C12---C13---C14---C9    −0.1 (3)       Ni1---P1---C39---C44    37.40 (16)
  C12---C13---C14---C1    −179.99 (18)   C44---C39---C40---C41   −0.8 (3)
  C10---C9---C14---C13    0.0 (3)        P1---C39---C40---C41    −178.37 (15)
  C8---C9---C14---C13     −179.55 (17)   C39---C40---C41---C42   −1.0 (3)
  C10---C9---C14---C1     179.97 (18)    C40---C41---C42---C43   1.7 (3)
  C8---C9---C14---C1      0.4 (3)        C41---C42---C43---C44   −0.6 (3)
  C2---C1---C14---C13     −177.90 (18)   C42---C43---C44---C39   −1.3 (3)
  Ni1---C1---C14---C13    3.3 (2)        C40---C39---C44---C43   2.0 (3)
  C2---C1---C14---C9      2.2 (3)        P1---C39---C44---C43    179.63 (15)
  Ni1---C1---C14---C9     −176.64 (14)   C39---P1---C45---C50    157.71 (17)
  C21---P2---C15---C16    −151.15 (17)   C38---P1---C45---C50    −93.51 (18)
  C27---P2---C15---C16    101.48 (18)    Ni1---P1---C45---C50    38.04 (19)
  Ni1---P2---C15---C16    −31.05 (19)    C39---P1---C45---C46    −28.5 (2)
  C21---P2---C15---C20    34.37 (18)     C38---P1---C45---C46    80.25 (19)
  C27---P2---C15---C20    −73.00 (18)    Ni1---P1---C45---C46    −148.20 (16)
  Ni1---P2---C15---C20    154.47 (14)    C50---C45---C46---C47   0.1 (3)
  C20---C15---C16---C17   −0.7 (3)       P1---C45---C46---C47    −173.63 (19)
  P2---C15---C16---C17    −175.27 (19)   C45---C46---C47---C48   1.0 (4)
  C15---C16---C17---C18   0.1 (4)        C46---C47---C48---C49   −1.4 (4)
  C16---C17---C18---C19   0.7 (4)        C47---C48---C49---C50   0.5 (4)
  C17---C18---C19---C20   −0.9 (4)       C46---C45---C50---C49   −1.0 (3)
  C18---C19---C20---C15   0.4 (3)        P1---C45---C50---C49    173.00 (16)
  C16---C15---C20---C19   0.4 (3)        C48---C49---C50---C45   0.7 (3)
  ----------------------- -------------- ----------------------- --------------
