(η5-Cyclo­penta­dien­yl){[3-(2,2-dicyano­ethen­yl)bicyclo­[2.2.1]hepta-2,5-dien-2-yl]ethyn­yl}(triphenyl­phosphine)nickel(II)

Gallagher, J.F.; Butler, P.; Manning, A.R.

doi:10.1107/S1600536808002328

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m411

doi:10.1107/S1600536808002328

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(η⁵-Cyclopentadienyl){[3-(2,2-dicyanoethenyl)bicyclo[2.2.1]hepta-2,5-dien-2-yl]ethynyl}(triphenylphosphine)nickel(II)

John F. Gallagher,^a ^* Peter Butler ^b and A. R. Manning ^b

^aSchool of Chemical Sciences, Dublin City University, Dublin 9, Ireland, and ^bDepartment of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland
^*Correspondence e-mail: john.gallagher@dcu.ie

(Received 18 January 2008; accepted 22 January 2008; online 25 January 2008)

The title compound, [Ni(C₅H₅)(C₁₃H₇N₂)(C₁₈H₁₅P)] or (η⁵-C₅H₅)(PPh₃)Ni—C≡C—C₇H₆—C(H)=C(CN)₂, contains an unusual disubstituted norbornadienyl (NBD) ligand containing ethynyl (–C≡C–) and dicyanovinyl [–C(H)=C(CN)₂] groups. Disorder is present in the NBD group with site occupancies of 0.636 (10) and 0.364 (10) for two distinct orientations. There are no strong hydrogen bonds and the primary interactions are weak C—H⋯π(arene) interactions.

Related literature

For related literature, see: Butler et al. (1998 , 2005 , 2007 ); Gallagher et al. (1998 , 2002 ); McArdle (1995 ); Whittal et al. (1998a ,b ).

Experimental

Crystal data

[Ni(C₅H₅)(C₁₃H₇N₂)(C₁₈H₁₅P)]
M_r = 577.28
Triclinic, $[P \overline 1]$
a = 10.7972 (16) Å
b = 11.8155 (14) Å
c = 12.1248 (14) Å
α = 73.169 (5)°
β = 78.153 (9)°
γ = 78.586 (9)°
V = 1433.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.76 mm⁻¹
T = 296 (1) K
0.50 × 0.40 × 0.30 mm

Data collection

Bruker P4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.716, T_max = 0.883 (expected range = 0.645–0.796)
7832 measured reflections
6787 independent reflections
4533 reflections with I > 2σ(I)
R_int = 0.029
3 standard reflections every 197 reflections intensity decay: 5%

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.108
S = 1.01
6787 reflections
407 parameters
94 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C33—H33⋯Cg1ⁱ	0.93	2.98	3.648 (4)	130
Symmetry code: (i) -x, -y+2, -z. Cg1 is the centroid of the cyclopentadienyl ring.

Data collection: XSCANS (Bruker, 1996 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PREP8 (Ferguson, 1998 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002328/lh2592sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808002328/lh2592Isup2.hkl

checkCIF report

Comment top

The acetylide linkage in Ni(η⁵-C₅H₅)(PPh₃)-C≡C—X complexes allows facile electronic communication between the electron rich Ni(η⁵-C₅H₅)(PPh₃) moiety and the X group (X = alkyl, arene) thus affecting the characteristic chemistry of both X and the acetylide linkage (Gallagher et al., 2002). However, if X is an electron withdrawing group the molecule is a donor-π-acceptor (D-π-A) system which may have non-linear optical (NLO) properties (Whittal et al., 1998a,b) although the phenyl derivative (X = C₆H₅) does not appear to be particularly effective.

We have demonstrated that polycylic hydrocarbons containing 1–5 aromatic rings can act as an electron-donor endgroup in D-π-A systems in the presence of suitable acceptors and have examined their behaviour when attached to the Ni(η⁵-C₅H₅)(PPh₃) donor moiety (Butler et al., 2005, 2007). The spectroscopic and electrochemical evidence suggests limited communication between either end of these Ni(η⁵-C₅H₅)(PPh₃)-C≡C—X systems at least in the ground state and is not sufficient to influence significant changes in the geometric data from diffraction measurements. Herein, we present an unusual norbornadiene derivative (I) (η⁵-C₅H₅)(PPh₃)Ni—C≡C-NBD-C(H)=C(CN)₂ (where NBD is a 2,3-substituted C₇H₆ group).

Molecule (I) has a half sandwich structure at the Ni^II centre and contains the σ-bonded ethynyl-2-norbornadienyl(methylidene)propanedinitrile ligand, a η⁵-C₅H₅ ring and triphenylphosphine bonded to the Ni^II atom. A view of the molecule with atomic numbering scheme is depicted (Fig. 1). The principal Ni-ligand dimensions include Ni1—P1 2.1417 (8) Å, Ni1—C1 1.839 (3) Å, Ni···Cg 1.7444 (16) Å (Cg is the cyclopentadienyl ring centroid), P1—Ni1—C1 87.86 (8)° and similar to geometric data in related derivatives (Gallagher et al., 1998, 2002; Butler et al., 1998, 2005). The acetylide –C≡C– and _spC—C_NBD bond lengths are 1.214 (4) Å and 1.403 (4) Å and similar to the geometric data reported for the dicyanovinyl derivative (II) (η⁵-C₅H₅)(PPh₃)Ni—C≡C—C(H)=C(C≡N)₂ (Gallagher et al., 2002). The two C=C bond lengths of 1.371 (4) Å (C3=C4) and 1.358 (4) Å (C5=C6) can be explained by an increase of delocalization along the conjugated metallo-ligand chain and the increase in bond lengths often observed in strained ring systems i.e. the C3=C4 in the NBD ring system.

The Ni—C≡C—C chain bond angles deviate slightly from linearity with Ni—C≡C 173.6 (2)° and C≡C—C 171.8 (3)°: this is greater than the two corresponding 176.6 (2)°/177.8 (3)° angles reported for (II) but similar to related systems (Butler et al., 1998) and this can be attributed mainly to crystal packing forces.

The η⁵-C₅H₅ ring is orthogonal to the P1/Ni1/C1 plane, 88.84 (10)°. Of interest is the relative co-planarity of atoms in the 11-atom chain Ni1—C1≡C2—C3=C4—C5=C6(C≡N)₂, where the Ni1 and C8 atoms deviate by a maximum of 0.334 (2) Å and 0.269 (2) Å from the 11-atom plane (the next greatest deviation is C2 by 0.159 (3) Å). This highlights the relative co-planarity of atoms along this chain increasing the potential for conjugation effects.

The closest intramolecular contact to Ni1 involves H22 with H22···Ni1 2.94 Å and C22—H22···Ni1 119° (C22 is the closest PPh₃ ortho-C to Ni1 at 3.476 (3) Å). The three Ni1—P—C angles vary as 111.28 (9)°, 113.62 (9)° and 118.31 (8)°. There is a small asymmetry in the PPh₃ ligand with four P—C—C angles in the range 119.1 (2)° to 122.5 (2)° at C21 and C31. However, at C41 these P—C—C angles are 117.53 (2)° and 124.5 (2)°. The three P—C_ipso···C_para angles are 179.50 (16)°, 177.56 (15)°, 175.90 (16)° and reflecting the greater phenyl asymmetry at C41.

In the absence of strong hydrogen bond donors or acceptors, C—H···π(arene) interactions involving the PPh₃ arene rings arise (details in Table) (Fig. 2). The C33···{C11,···,C15} distances are in the range 3.618 (4) Å to 4.023 (4) Å and C—H···C angles (in Cg1) vary from 108° to 147°.

Related literature top

For related literature, see: Butler et al. (1998, 2005, 2007); Gallagher et al. (1998, 2002); McArdle (1995); Sheldrick (2008); Whittal et al. (1998a,b).

Experimental top

Compound (I) was prepared according to literature methods (Butler et al., 1998, 2005, 2007), (Gallagher et al., 2002) and involves hydrolysis of an acetal precursor to an aldehyde and subsequent reaction with malonitrile H₂C(C≡N)₂ to give the dicyanovinyl derivative (title compound). Yield 95%. Crystals suitable for X-ray diffraction were grown from Et₂O/hexane. ¹H NMR (δ, 270 MHz, CDCl₃): 7.68 - 7.37 (m, 15H, PPh₃), 6.68 (s, 1H, –CH=), 6.63 and 6.29 (d, 2H, –C(H)=C(H)-), 5.26 (s, 5H, Cp), 4.31, 3.04 (s, 2H, bridgehead H), 1.78 (dd, ¹J_HH = 8 Hz, 2H, µ-CH₂). ¹³C NMR (δ, 270 MHz, CDCl₃): 165.81 (s, Ni—C≡C), 148.59 and 147.43 (s, C₃ and C₄), 142.61 and 139.89 (s, C_{52 A/B} and C_{53 A/B}), 132.95 (d, ¹J_CP = 50 Hz, Ni—C), 133.7 - 128.4 (m, PPh₃), 119.33 (s, C(C≡N)₂, 116.59 and 115.37 (s, C≡N), 93.27 (s, Cp), 67.7 (s, µ-CH₂), 57.85 and 47.22 (s, bridgehead C). IR (ν _C_≡_C, cm^-1): 2150 (CH₂Cl₂); 2152 (KBr) and (ν _C_≡_N, cm^-1): 2216 (CH₂Cl₂); 2216 (KBr). Microanalysis: calculated for C₃₆H₂₁N₂PNi: C, 74.9, H, 4.7, N 4.8; found: C, 74.6, H, 5.2, N 4.8.

Structure description top

For related literature, see: Butler et al. (1998, 2005, 2007); Gallagher et al. (1998, 2002); McArdle (1995); Sheldrick (2008); Whittal et al. (1998a,b).

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS (Bruker, 1996); data reduction: XSCANS (Bruker, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PREP8 (Ferguson, 1998).

Figures top

	Fig. 1. A view of the major conformation of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 20% probability level.
	Fig. 2. A view of the NBD disorder in (I): the (cp)(PPh₃)Ni—C atoms are omitted for clarity. Displacement ellipsoids are drawn at the 20% probability level.
	Fig. 3. A view of the principal C—H···π(arene) interaction and unit cell in (I) with atoms depicted as their van der Waals spheres. The atom labels C33—H33 and # (cp ring) signify the interaction listed in Table 1.

(η⁵-Cyclopentadienyl){[3-(2,2-dicyanoethenyl)bicyclo[2.2.1]hepta-2,5- dien-2-yl]ethynyl}(triphenylphosphine)nickel(II) top

Crystal data top

[Ni(C₅H₅)(C₁₃H₇N₂)(C₁₈H₁₅P)]	Z = 2
M_r = 577.28	F(000) = 600
Triclinic, P1	D_x = 1.338 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.7972 (16) Å	Cell parameters from 40 reflections
b = 11.8155 (14) Å	θ = 3.6–14.9°
c = 12.1248 (14) Å	µ = 0.76 mm⁻¹
α = 73.169 (5)°	T = 296 K
β = 78.153 (9)°	Block, green
γ = 78.586 (9)°	0.50 × 0.40 × 0.30 mm
V = 1433.1 (3) Å³

Data collection top

Bruker P4 diffractometer	4533 reflections with I > 2σ(I)
Radiation source: X-ray tube	R_int = 0.029
Graphite monochromator	θ_max = 28.0°, θ_min = 2.0°
ω scans	h = −1→14
Absorption correction: ψ scan (North et al., 1968)	k = −14→15
T_min = 0.716, T_max = 0.883	l = −15→16
7832 measured reflections	3 standard reflections every 197 reflections
6787 independent reflections	intensity decay: 5%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0422P)² + 0.2761P] where P = (F_o² + 2F_c²)/3
6787 reflections	(Δ/σ)_max = 0.001
407 parameters	Δρ_max = 0.33 e Å⁻³
94 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Ni(C₅H₅)(C₁₃H₇N₂)(C₁₈H₁₅P)]	γ = 78.586 (9)°
M_r = 577.28	V = 1433.1 (3) Å³
Triclinic, P1	Z = 2
a = 10.7972 (16) Å	Mo Kα radiation
b = 11.8155 (14) Å	µ = 0.76 mm⁻¹
c = 12.1248 (14) Å	T = 296 K
α = 73.169 (5)°	0.50 × 0.40 × 0.30 mm
β = 78.153 (9)°

Data collection top

Bruker P4 diffractometer	4533 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.029
T_min = 0.716, T_max = 0.883	3 standard reflections every 197 reflections
7832 measured reflections	intensity decay: 5%
6787 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	94 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.01	Δρ_max = 0.33 e Å⁻³
6787 reflections	Δρ_min = −0.25 e Å⁻³
407 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ni1	0.27893 (3)	0.93823 (3)	0.16592 (3)	0.04182 (11)
P1	0.25181 (6)	0.75680 (6)	0.25072 (6)	0.03890 (16)
C7	0.3069 (4)	0.8014 (3)	0.7760 (3)	0.0742 (10)
N7	0.2068 (4)	0.8081 (4)	0.8281 (3)	0.1087 (13)
C8	0.5323 (3)	0.7390 (3)	0.7788 (3)	0.0656 (9)
N8	0.6099 (3)	0.6948 (3)	0.8358 (3)	0.0900 (10)
C11	0.3133 (4)	1.0983 (3)	0.0448 (3)	0.0775 (11)
C12	0.1960 (4)	1.1199 (3)	0.1177 (3)	0.0754 (10)
C13	0.1155 (3)	1.0515 (3)	0.1036 (3)	0.0673 (9)
C14	0.1824 (3)	0.9861 (3)	0.0235 (3)	0.0630 (9)
C15	0.3020 (3)	1.0210 (3)	−0.0173 (3)	0.0713 (10)
C21	0.1743 (2)	0.7343 (2)	0.4027 (2)	0.0411 (6)
C22	0.1526 (3)	0.8261 (3)	0.4567 (2)	0.0525 (7)
C23	0.0924 (3)	0.8097 (3)	0.5709 (3)	0.0641 (8)
C24	0.0546 (3)	0.7015 (3)	0.6334 (3)	0.0654 (9)
C25	0.0729 (3)	0.6103 (3)	0.5809 (3)	0.0628 (8)
C26	0.1314 (3)	0.6267 (3)	0.4661 (2)	0.0538 (7)
C31	0.1525 (2)	0.6869 (2)	0.1912 (2)	0.0404 (6)
C32	0.0282 (3)	0.7414 (3)	0.1783 (2)	0.0510 (7)
C33	−0.0502 (3)	0.6905 (3)	0.1360 (3)	0.0564 (8)
C34	−0.0066 (3)	0.5840 (3)	0.1077 (3)	0.0621 (8)
C35	0.1157 (3)	0.5280 (3)	0.1206 (3)	0.0638 (8)
C36	0.1958 (3)	0.5797 (3)	0.1611 (2)	0.0537 (7)
C41	0.4038 (2)	0.6565 (2)	0.2487 (2)	0.0416 (6)
C42	0.4416 (3)	0.5703 (3)	0.3439 (3)	0.0588 (8)
C43	0.5589 (3)	0.4972 (3)	0.3331 (3)	0.0739 (10)
C44	0.6380 (3)	0.5098 (3)	0.2283 (3)	0.0677 (9)
C45	0.6005 (3)	0.5934 (3)	0.1337 (3)	0.0832 (12)
C46	0.4849 (3)	0.6665 (3)	0.1434 (3)	0.0703 (10)
C1	0.3981 (2)	0.9205 (2)	0.2607 (2)	0.0437 (6)
C2	0.4765 (3)	0.8968 (2)	0.3259 (2)	0.0474 (6)
C3	0.5745 (2)	0.8557 (3)	0.3944 (2)	0.0521 (7)
C4	0.5668 (3)	0.8212 (3)	0.5134 (3)	0.0717 (10)
C5	0.4523 (3)	0.8275 (3)	0.5920 (3)	0.0650 (9)
C6	0.4332 (3)	0.7919 (3)	0.7104 (3)	0.0607 (8)
C51A	0.7154 (7)	0.8267 (12)	0.3422 (11)	0.055 (3)	0.636 (10)
C52A	0.7821 (10)	0.9071 (9)	0.3796 (7)	0.067 (2)	0.636 (10)
C53A	0.7758 (7)	0.8686 (6)	0.4953 (7)	0.067 (2)	0.636 (10)
C55A	0.7544 (17)	0.7069 (12)	0.4307 (8)	0.055 (2)	0.636 (10)
C54A	0.7055 (5)	0.7614 (7)	0.5348 (6)	0.0548 (19)	0.636 (10)
C51B	0.7190 (9)	0.841 (2)	0.3499 (18)	0.055 (6)	0.364 (10)
C52B	0.754 (3)	0.709 (2)	0.4038 (14)	0.070 (6)	0.364 (10)
C53B	0.7446 (10)	0.6940 (10)	0.5189 (12)	0.065 (3)	0.364 (10)
C55B	0.7770 (16)	0.8884 (15)	0.4301 (11)	0.056 (4)	0.364 (10)
C54B	0.7028 (9)	0.8154 (11)	0.5398 (10)	0.064 (4)	0.364 (10)
H11	0.3866	1.1310	0.0395	0.093*
H12	0.1772	1.1712	0.1663	0.090*
H13	0.0312	1.0485	0.1404	0.081*
H14	0.1513	0.9291	0.0017	0.076*
H15	0.3630	0.9968	−0.0755	0.086*
H22	0.1787	0.8994	0.4158	0.063*
H23	0.0772	0.8724	0.6060	0.077*
H24	0.0166	0.6905	0.7112	0.078*
H25	0.0462	0.5375	0.6224	0.075*
H26	0.1424	0.5648	0.4304	0.065*
H32	−0.0026	0.8131	0.1986	0.061*
H33	−0.1328	0.7286	0.1267	0.068*
H34	−0.0599	0.5495	0.0798	0.074*
H35	0.1448	0.4552	0.1021	0.077*
H36	0.2791	0.5423	0.1681	0.064*
H42	0.3886	0.5607	0.4159	0.071*
H43	0.5838	0.4390	0.3980	0.089*
H44	0.7170	0.4615	0.2220	0.081*
H45	0.6533	0.6015	0.0617	0.100*
H46	0.4607	0.7238	0.0776	0.084*
H5	0.3790	0.8608	0.5582	0.078*
H51A	0.7338	0.8274	0.2595	0.066*	0.636 (10)
H52A	0.8206	0.9716	0.3310	0.081*	0.636 (10)
H53A	0.8084	0.9013	0.5425	0.080*	0.636 (10)
H55A	0.7084	0.6438	0.4318	0.066*	0.636 (10)
H55B	0.8459	0.6800	0.4210	0.066*	0.636 (10)
H54A	0.7147	0.7083	0.6123	0.066*	0.636 (10)
H51B	0.7462	0.8700	0.2657	0.066*	0.364 (10)
H52B	0.7767	0.6490	0.3646	0.085*	0.364 (10)
H53B	0.7612	0.6224	0.5747	0.078*	0.364 (10)
H55C	0.8690	0.8656	0.4247	0.067*	0.364 (10)
H55D	0.7539	0.9740	0.4199	0.067*	0.364 (10)
H54B	0.7105	0.8256	0.6154	0.077*	0.364 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.03662 (18)	0.0448 (2)	0.04238 (19)	−0.00811 (14)	−0.01386 (14)	−0.00215 (14)
P1	0.0332 (3)	0.0436 (4)	0.0394 (3)	−0.0066 (3)	−0.0086 (3)	−0.0073 (3)
C7	0.077 (3)	0.086 (3)	0.0514 (19)	0.006 (2)	−0.0049 (18)	−0.0218 (18)
N7	0.084 (3)	0.150 (4)	0.079 (2)	0.007 (2)	0.006 (2)	−0.039 (2)
C8	0.079 (2)	0.068 (2)	0.0507 (18)	−0.0046 (18)	−0.0169 (17)	−0.0155 (16)
N8	0.105 (3)	0.099 (2)	0.0661 (19)	0.004 (2)	−0.0413 (19)	−0.0155 (17)
C11	0.071 (2)	0.061 (2)	0.088 (3)	−0.0264 (18)	−0.039 (2)	0.0289 (19)
C12	0.096 (3)	0.0448 (18)	0.084 (3)	0.0104 (18)	−0.044 (2)	−0.0085 (17)
C13	0.0409 (16)	0.077 (2)	0.069 (2)	0.0022 (16)	−0.0194 (15)	0.0032 (18)
C14	0.067 (2)	0.065 (2)	0.0586 (19)	−0.0101 (17)	−0.0347 (17)	−0.0017 (16)
C15	0.067 (2)	0.084 (2)	0.0422 (17)	−0.0023 (19)	−0.0077 (16)	0.0097 (16)
C21	0.0331 (13)	0.0500 (15)	0.0407 (14)	−0.0073 (11)	−0.0073 (11)	−0.0105 (12)
C22	0.0447 (15)	0.0619 (18)	0.0533 (17)	−0.0163 (13)	0.0014 (13)	−0.0192 (14)
C23	0.0578 (19)	0.084 (2)	0.0586 (19)	−0.0153 (17)	0.0001 (15)	−0.0341 (18)
C24	0.0547 (19)	0.092 (3)	0.0448 (17)	−0.0148 (17)	−0.0003 (14)	−0.0126 (17)
C25	0.065 (2)	0.065 (2)	0.0507 (18)	−0.0206 (16)	−0.0039 (15)	0.0004 (15)
C26	0.0585 (18)	0.0542 (17)	0.0488 (16)	−0.0136 (14)	−0.0090 (14)	−0.0095 (13)
C31	0.0359 (13)	0.0494 (15)	0.0358 (13)	−0.0089 (11)	−0.0054 (10)	−0.0092 (11)
C32	0.0391 (14)	0.0566 (17)	0.0605 (18)	−0.0020 (12)	−0.0106 (13)	−0.0216 (14)
C33	0.0375 (15)	0.077 (2)	0.0587 (18)	−0.0057 (14)	−0.0137 (13)	−0.0209 (16)
C34	0.0533 (18)	0.091 (2)	0.0549 (18)	−0.0209 (17)	−0.0097 (14)	−0.0317 (17)
C35	0.062 (2)	0.072 (2)	0.072 (2)	−0.0083 (16)	−0.0144 (16)	−0.0401 (18)
C36	0.0434 (15)	0.0634 (19)	0.0574 (18)	−0.0028 (13)	−0.0097 (13)	−0.0228 (15)
C41	0.0357 (13)	0.0417 (14)	0.0466 (15)	−0.0057 (11)	−0.0092 (11)	−0.0084 (11)
C42	0.0584 (18)	0.070 (2)	0.0435 (16)	0.0057 (15)	−0.0153 (14)	−0.0132 (14)
C43	0.070 (2)	0.078 (2)	0.068 (2)	0.0182 (18)	−0.0344 (19)	−0.0136 (18)
C44	0.0469 (17)	0.062 (2)	0.091 (3)	0.0065 (15)	−0.0169 (18)	−0.0219 (19)
C45	0.0493 (19)	0.088 (3)	0.078 (2)	0.0088 (18)	0.0132 (17)	0.002 (2)
C46	0.0476 (17)	0.073 (2)	0.061 (2)	0.0035 (16)	0.0039 (15)	0.0104 (16)
C1	0.0410 (14)	0.0420 (14)	0.0462 (15)	−0.0084 (11)	−0.0094 (12)	−0.0051 (12)
C2	0.0438 (15)	0.0529 (16)	0.0435 (15)	−0.0095 (12)	−0.0107 (12)	−0.0050 (12)
C3	0.0402 (15)	0.0603 (18)	0.0513 (16)	−0.0047 (13)	−0.0125 (13)	−0.0055 (14)
C4	0.0404 (16)	0.111 (3)	0.0523 (18)	0.0029 (17)	−0.0173 (14)	−0.0063 (18)
C5	0.0476 (17)	0.088 (2)	0.0522 (18)	0.0031 (16)	−0.0150 (14)	−0.0107 (17)
C6	0.0596 (19)	0.067 (2)	0.0518 (18)	0.0048 (15)	−0.0122 (15)	−0.0176 (15)
C51A	0.045 (6)	0.068 (6)	0.049 (5)	−0.012 (4)	−0.009 (4)	−0.007 (4)
C52A	0.041 (3)	0.067 (4)	0.086 (6)	−0.011 (3)	−0.016 (5)	−0.001 (5)
C53A	0.048 (4)	0.076 (4)	0.090 (6)	−0.008 (3)	−0.037 (4)	−0.025 (4)
C55A	0.046 (4)	0.051 (4)	0.060 (5)	0.008 (3)	−0.018 (4)	−0.007 (3)
C54A	0.044 (3)	0.054 (5)	0.060 (3)	0.018 (3)	−0.024 (3)	−0.012 (3)
C51B	0.035 (9)	0.061 (9)	0.060 (9)	0.009 (7)	−0.014 (7)	−0.010 (7)
C52B	0.059 (9)	0.070 (10)	0.081 (10)	−0.008 (7)	−0.010 (9)	−0.019 (8)
C53B	0.047 (6)	0.061 (6)	0.077 (7)	−0.005 (5)	−0.023 (5)	0.005 (6)
C55B	0.048 (6)	0.070 (8)	0.057 (9)	−0.019 (5)	−0.024 (8)	−0.007 (8)
C54B	0.068 (8)	0.061 (8)	0.056 (6)	0.014 (7)	−0.017 (5)	−0.016 (6)

Geometric parameters (Å, º) top

Ni1—C1	1.839 (3)	C23—H23	0.9300
Ni1—C11	2.078 (3)	C24—C25	1.366 (5)
Ni1—C12	2.116 (3)	C24—H24	0.9300
Ni1—C13	2.122 (3)	C25—C26	1.380 (4)
Ni1—C14	2.081 (3)	C25—H25	0.9300
Ni1—C15	2.136 (3)	C26—H26	0.9300
Ni1—P1	2.1417 (8)	C31—C36	1.385 (4)
P1—C21	1.827 (3)	C31—C32	1.388 (3)
P1—C31	1.835 (3)	C32—C33	1.378 (4)
P1—C41	1.824 (3)	C32—H32	0.9300
C1—C2	1.214 (3)	C33—C34	1.368 (4)
C2—C3	1.403 (4)	C33—H33	0.9300
C3—C4	1.371 (4)	C34—C35	1.373 (4)
C3—C51A	1.535 (7)	C34—H34	0.9300
C3—C51B	1.535 (9)	C35—C36	1.385 (4)
C4—C5	1.400 (4)	C35—H35	0.9300
C4—C54B	1.550 (9)	C36—H36	0.9300
C4—C54A	1.563 (6)	C41—C42	1.373 (4)
C5—C6	1.358 (4)	C41—C46	1.380 (4)
C5—H5	0.9300	C42—C43	1.390 (4)
C7—N7	1.135 (5)	C42—H42	0.9300
C7—C6	1.432 (5)	C43—C44	1.364 (5)
C8—N8	1.144 (4)	C43—H43	0.9300
C8—C6	1.423 (4)	C44—C45	1.354 (5)
C11—C15	1.377 (5)	C44—H44	0.9300
C11—C12	1.412 (5)	C45—C46	1.375 (4)
C11—H11	0.9300	C45—H45	0.9300
C12—C13	1.363 (5)	C46—H46	0.9300
C12—H12	0.9300	C51A—C52A	1.510 (8)
C13—C14	1.410 (5)	C51A—C55A	1.550 (7)
C13—H13	0.9300	C52A—C53A	1.335 (7)
C14—C15	1.382 (5)	C53A—C54A	1.514 (7)
C14—H14	0.9300	C55A—C54A	1.532 (8)
C15—H15	0.9300	C51B—C52B	1.510 (10)
C21—C22	1.381 (4)	C51B—C55B	1.536 (9)
C21—C26	1.394 (4)	C52B—C53B	1.340 (9)
C22—C23	1.379 (4)	C53B—C54B	1.493 (9)
C22—H22	0.9300	C55B—C54B	1.525 (9)
C23—C24	1.377 (5)

C1—Ni1—C11	100.90 (12)	C25—C26—H26	119.4
C1—Ni1—C14	163.39 (12)	C21—C26—H26	119.4
C11—Ni1—C14	64.40 (14)	C36—C31—C32	118.4 (2)
C1—Ni1—C12	109.61 (13)	C36—C31—P1	122.5 (2)
C11—Ni1—C12	39.34 (14)	C32—C31—P1	119.1 (2)
C14—Ni1—C12	64.61 (14)	C33—C32—C31	120.8 (3)
C1—Ni1—C13	143.35 (14)	C33—C32—H32	119.6
C11—Ni1—C13	64.26 (13)	C31—C32—H32	119.6
C14—Ni1—C13	39.18 (13)	C34—C33—C32	120.1 (3)
C12—Ni1—C13	37.52 (13)	C34—C33—H33	119.9
C1—Ni1—C15	125.25 (13)	C32—C33—H33	119.9
C11—Ni1—C15	38.10 (14)	C33—C34—C35	120.0 (3)
C14—Ni1—C15	38.24 (13)	C33—C34—H34	120.0
C12—Ni1—C15	64.59 (15)	C35—C34—H34	120.0
C13—Ni1—C15	64.33 (13)	C34—C35—C36	120.1 (3)
C1—Ni1—P1	87.86 (8)	C34—C35—H35	119.9
C11—Ni1—P1	165.01 (13)	C36—C35—H35	119.9
C14—Ni1—P1	104.95 (10)	C35—C36—C31	120.4 (3)
C12—Ni1—P1	147.85 (12)	C35—C36—H36	119.8
C13—Ni1—P1	114.96 (10)	C31—C36—H36	119.8
C15—Ni1—P1	127.08 (12)	C42—C41—C46	117.9 (3)
C41—P1—C21	107.44 (12)	C42—C41—P1	124.5 (2)
C41—P1—C31	103.20 (12)	C46—C41—P1	117.5 (2)
C21—P1—C31	101.86 (11)	C41—C42—C43	120.2 (3)
C41—P1—Ni1	111.28 (9)	C41—C42—H42	119.9
C21—P1—Ni1	113.62 (9)	C43—C42—H42	119.9
C31—P1—Ni1	118.31 (8)	C44—C43—C42	120.8 (3)
N7—C7—C6	179.5 (4)	C44—C43—H43	119.6
N8—C8—C6	178.3 (4)	C42—C43—H43	119.6
C15—C11—C12	109.1 (3)	C45—C44—C43	119.4 (3)
C15—C11—Ni1	73.25 (19)	C45—C44—H44	120.3
C12—C11—Ni1	71.79 (19)	C43—C44—H44	120.3
C15—C11—H11	125.5	C44—C45—C46	120.4 (3)
C12—C11—H11	125.5	C44—C45—H45	119.8
Ni1—C11—H11	121.2	C46—C45—H45	119.8
C13—C12—C11	107.2 (3)	C45—C46—C41	121.4 (3)
C13—C12—Ni1	71.49 (19)	C45—C46—H46	119.3
C11—C12—Ni1	68.86 (18)	C41—C46—H46	119.3
C13—C12—H12	126.4	C2—C1—Ni1	173.6 (2)
C11—C12—H12	126.4	C1—C2—C3	171.8 (3)
Ni1—C12—H12	124.9	C4—C3—C2	129.7 (3)
C12—C13—C14	108.0 (3)	C4—C3—C51A	107.3 (5)
C12—C13—Ni1	70.99 (18)	C2—C3—C51A	122.6 (5)
C14—C13—Ni1	68.82 (16)	C4—C3—C51B	103.7 (8)
C12—C13—H13	126.0	C2—C3—C51B	126.6 (8)
C14—C13—H13	126.0	C3—C4—C5	124.3 (3)
Ni1—C13—H13	125.7	C3—C4—C54B	106.7 (5)
C15—C14—C13	108.5 (3)	C5—C4—C54B	126.2 (5)
C15—C14—Ni1	73.05 (18)	C3—C4—C54A	104.6 (3)
C13—C14—Ni1	72.00 (17)	C5—C4—C54A	130.6 (3)
C15—C14—H14	125.7	C6—C5—C4	129.2 (3)
C13—C14—H14	125.7	C6—C5—H5	115.4
Ni1—C14—H14	121.0	C4—C5—H5	115.4
C11—C15—C14	106.9 (3)	C5—C6—C8	124.3 (3)
C11—C15—Ni1	68.65 (18)	C5—C6—C7	120.9 (3)
C14—C15—Ni1	68.71 (17)	C8—C6—C7	114.7 (3)
C11—C15—H15	126.6	C52A—C51A—C3	103.7 (8)
C14—C15—H15	126.6	C52A—C51A—C55A	99.1 (10)
Ni1—C15—H15	127.6	C3—C51A—C55A	100.3 (9)
C22—C21—C26	118.1 (2)	C52A—C51A—H51A	117.0
C22—C21—P1	120.3 (2)	C53A—C52A—C51A	107.5 (9)
C26—C21—P1	121.5 (2)	C52A—C53A—C54A	106.7 (7)
C23—C22—C21	120.3 (3)	C54A—C55A—C51A	92.3 (8)
C23—C22—H22	119.8	C53A—C54A—C55A	99.9 (8)
C21—C22—H22	119.8	C53A—C54A—C4	101.6 (5)
C24—C23—C22	120.8 (3)	C55A—C54A—C4	102.2 (7)
C24—C23—H23	119.6	C52B—C51B—C3	99.6 (17)
C22—C23—H23	119.6	C52B—C51B—C55B	98.2 (18)
C25—C24—C23	119.8 (3)	C3—C51B—C55B	105.0 (11)
C25—C24—H24	120.1	C53B—C52B—C51B	107.1 (19)
C23—C24—H24	120.1	C52B—C53B—C54B	106.5 (15)
C24—C25—C26	119.7 (3)	C54B—C55B—C51B	92.3 (12)
C24—C25—H25	120.1	C53B—C54B—C55B	99.2 (11)
C26—C25—H25	120.1	C53B—C54B—C4	92.1 (8)
C25—C26—C21	121.2 (3)	C55B—C54B—C4	107.0 (9)

C1—Ni1—P1—C41	−52.45 (12)	C41—P1—C21—C26	−66.4 (2)
C11—Ni1—P1—C41	73.8 (4)	C31—P1—C21—C26	41.7 (2)
C14—Ni1—P1—C41	116.83 (14)	Ni1—P1—C21—C26	170.08 (19)
C12—Ni1—P1—C41	−177.3 (2)	C26—C21—C22—C23	1.3 (4)
C13—Ni1—P1—C41	157.32 (14)	P1—C21—C22—C23	179.0 (2)
C15—Ni1—P1—C41	81.63 (15)	C21—C22—C23—C24	0.9 (5)
C1—Ni1—P1—C21	68.98 (12)	C22—C23—C24—C25	−2.1 (5)
C11—Ni1—P1—C21	−164.7 (4)	C23—C24—C25—C26	1.2 (5)
C14—Ni1—P1—C21	−121.74 (14)	C24—C25—C26—C21	1.1 (5)
C12—Ni1—P1—C21	−55.9 (2)	C22—C21—C26—C25	−2.3 (4)
C13—Ni1—P1—C21	−81.26 (14)	P1—C21—C26—C25	−180.0 (2)
C15—Ni1—P1—C21	−156.95 (14)	C41—P1—C31—C36	2.6 (3)
C1—Ni1—P1—C31	−171.65 (13)	C21—P1—C31—C36	−108.7 (2)
C11—Ni1—P1—C31	−45.4 (4)	Ni1—P1—C31—C36	125.9 (2)
C14—Ni1—P1—C31	−2.38 (14)	C41—P1—C31—C32	−179.1 (2)
C12—Ni1—P1—C31	63.5 (2)	C21—P1—C31—C32	69.6 (2)
C13—Ni1—P1—C31	38.11 (15)	Ni1—P1—C31—C32	−55.8 (2)
C15—Ni1—P1—C31	−37.58 (15)	C36—C31—C32—C33	−0.4 (4)
C1—Ni1—C11—C15	135.0 (2)	P1—C31—C32—C33	−178.7 (2)
C14—Ni1—C11—C15	−36.8 (2)	C31—C32—C33—C34	1.0 (5)
C12—Ni1—C11—C15	−117.3 (3)	C32—C33—C34—C35	−0.5 (5)
C13—Ni1—C11—C15	−80.5 (2)	C33—C34—C35—C36	−0.7 (5)
P1—Ni1—C11—C15	10.1 (5)	C34—C35—C36—C31	1.3 (5)
C1—Ni1—C11—C12	−107.7 (2)	C32—C31—C36—C35	−0.8 (4)
C14—Ni1—C11—C12	80.5 (2)	P1—C31—C36—C35	177.5 (2)
C13—Ni1—C11—C12	36.8 (2)	C21—P1—C41—C42	7.7 (3)
C15—Ni1—C11—C12	117.3 (3)	C31—P1—C41—C42	−99.5 (3)
P1—Ni1—C11—C12	127.4 (4)	Ni1—P1—C41—C42	132.6 (2)
C15—C11—C12—C13	2.6 (4)	C21—P1—C41—C46	−173.8 (2)
Ni1—C11—C12—C13	−61.6 (2)	C31—P1—C41—C46	79.0 (3)
C15—C11—C12—Ni1	64.2 (2)	Ni1—P1—C41—C46	−48.9 (3)
C1—Ni1—C12—C13	−159.1 (2)	C46—C41—C42—C43	0.8 (5)
C11—Ni1—C12—C13	117.7 (3)	P1—C41—C42—C43	179.3 (2)
C14—Ni1—C12—C13	37.8 (2)	C41—C42—C43—C44	0.0 (5)
C15—Ni1—C12—C13	80.3 (2)	C42—C43—C44—C45	−1.0 (6)
P1—Ni1—C12—C13	−39.6 (3)	C43—C44—C45—C46	1.2 (6)
C1—Ni1—C12—C11	83.2 (2)	C44—C45—C46—C41	−0.4 (6)
C14—Ni1—C12—C11	−79.9 (2)	C42—C41—C46—C45	−0.6 (5)
C13—Ni1—C12—C11	−117.7 (3)	C2—C3—C4—C5	−3.8 (6)
C15—Ni1—C12—C11	−37.4 (2)	C51A—C3—C4—C5	−176.5 (6)
P1—Ni1—C12—C11	−157.29 (19)	C51B—C3—C4—C5	175.5 (9)
C11—C12—C13—C14	0.8 (4)	C2—C3—C4—C54B	−166.0 (6)
Ni1—C12—C13—C14	−59.1 (2)	C51A—C3—C4—C54B	21.2 (8)
C11—C12—C13—Ni1	59.9 (2)	C51B—C3—C4—C54B	13.3 (10)
C1—Ni1—C13—C12	34.2 (3)	C2—C3—C4—C54A	168.9 (4)
C11—Ni1—C13—C12	−38.6 (2)	C51A—C3—C4—C54A	−3.8 (7)
C14—Ni1—C13—C12	−118.9 (3)	C51B—C3—C4—C54A	−11.8 (10)
C15—Ni1—C13—C12	−81.0 (2)	C3—C4—C5—C6	177.3 (4)
P1—Ni1—C13—C12	158.0 (2)	C54B—C4—C5—C6	−24.0 (8)
C1—Ni1—C13—C14	153.1 (2)	C54A—C4—C5—C6	6.6 (8)
C11—Ni1—C13—C14	80.3 (2)	C4—C5—C6—C8	0.0 (6)
C12—Ni1—C13—C14	118.9 (3)	C4—C5—C6—C7	−177.4 (4)
C15—Ni1—C13—C14	37.9 (2)	C4—C3—C51A—C52A	−64.5 (9)
P1—Ni1—C13—C14	−83.1 (2)	C2—C3—C51A—C52A	122.1 (7)
C12—C13—C14—C15	−3.9 (3)	C4—C3—C51A—C55A	37.6 (8)
Ni1—C13—C14—C15	−64.4 (2)	C2—C3—C51A—C55A	−135.8 (7)
C12—C13—C14—Ni1	60.5 (2)	C3—C51A—C52A—C53A	67.7 (11)
C1—Ni1—C14—C15	7.4 (6)	C55A—C51A—C52A—C53A	−35.4 (11)
C11—Ni1—C14—C15	36.7 (2)	C51A—C52A—C53A—C54A	0.5 (11)
C12—Ni1—C14—C15	80.5 (2)	C52A—C51A—C55A—C54A	52.8 (10)
C13—Ni1—C14—C15	116.7 (3)	C3—C51A—C55A—C54A	−53.0 (10)
P1—Ni1—C14—C15	−132.0 (2)	C52A—C53A—C54A—C55A	35.2 (10)
C1—Ni1—C14—C13	−109.2 (5)	C52A—C53A—C54A—C4	−69.6 (9)
C11—Ni1—C14—C13	−80.0 (2)	C51A—C55A—C54A—C53A	−52.8 (9)
C12—Ni1—C14—C13	−36.2 (2)	C51A—C55A—C54A—C4	51.4 (10)
C15—Ni1—C14—C13	−116.7 (3)	C3—C4—C54A—C53A	71.0 (6)
P1—Ni1—C14—C13	111.32 (19)	C5—C4—C54A—C53A	−116.9 (6)
C12—C11—C15—C14	−5.0 (3)	C3—C4—C54A—C55A	−31.8 (8)
Ni1—C11—C15—C14	58.3 (2)	C5—C4—C54A—C55A	140.2 (8)
C12—C11—C15—Ni1	−63.3 (2)	C4—C3—C51B—C52B	59.8 (12)
C13—C14—C15—C11	5.5 (3)	C2—C3—C51B—C52B	−120.9 (13)
Ni1—C14—C15—C11	−58.2 (2)	C4—C3—C51B—C55B	−41.5 (15)
C13—C14—C15—Ni1	63.7 (2)	C2—C3—C51B—C55B	137.8 (10)
C1—Ni1—C15—C11	−58.3 (3)	C3—C51B—C52B—C53B	−72 (2)
C14—Ni1—C15—C11	119.1 (3)	C55B—C51B—C52B—C53B	35 (2)
C12—Ni1—C15—C11	38.6 (2)	C51B—C52B—C53B—C54B	1 (3)
C13—Ni1—C15—C11	80.3 (2)	C52B—C51B—C55B—C54B	−53.8 (15)
P1—Ni1—C15—C11	−176.74 (18)	C3—C51B—C55B—C54B	48.5 (15)
C1—Ni1—C15—C14	−177.4 (2)	C52B—C53B—C54B—C55B	−36.9 (19)
C11—Ni1—C15—C14	−119.1 (3)	C52B—C53B—C54B—C4	70.7 (18)
C12—Ni1—C15—C14	−80.5 (2)	C51B—C55B—C54B—C53B	55.0 (12)
C13—Ni1—C15—C14	−38.8 (2)	C51B—C55B—C54B—C4	−40.0 (12)
P1—Ni1—C15—C14	64.1 (2)	C3—C4—C54B—C53B	−81.7 (8)
C41—P1—C21—C22	116.0 (2)	C5—C4—C54B—C53B	116.5 (7)
C31—P1—C21—C22	−135.9 (2)	C3—C4—C54B—C55B	18.6 (11)
Ni1—P1—C21—C22	−7.6 (2)	C5—C4—C54B—C55B	−143.2 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···Cg1ⁱ	0.93	2.98	3.648 (4)	130

Symmetry code: (i) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula	[Ni(C₅H₅)(C₁₃H₇N₂)(C₁₈H₁₅P)]
M_r	577.28
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.7972 (16), 11.8155 (14), 12.1248 (14)
α, β, γ (°)	73.169 (5), 78.153 (9), 78.586 (9)
V (Å³)	1433.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.50 × 0.40 × 0.30

Data collection
Diffractometer	Bruker P4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.716, 0.883
No. of measured, independent and observed [I > 2σ(I)] reflections	7832, 6787, 4533
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.108, 1.01
No. of reflections	6787
No. of parameters	407
No. of restraints	94
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.25

Computer programs: XSCANS (Bruker, 1996), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 2008) and PREP8 (Ferguson, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···Cg1ⁱ	0.93	2.98	3.648 (4)	130

Symmetry code: (i) −x, −y+2, −z.

Acknowledgements

JFG thanks Dublin City University for the purchase of a Bruker P4 diffractometer and computer system in 1998.

References

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