(η5-Cyclo­penta­dien­yl)(η6-1,2-dipyrrolidin-1-ylbenzene)iron(II) hexa­fluoridophosphate

Jenkins, H.A.; Masuda, J.D.; Piórko, A.

doi:10.1107/S1600536809028116

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m966

doi:10.1107/S1600536809028116

Open

access

(η⁵-Cyclopentadienyl)(η⁶-1,2-dipyrrolidin-1-ylbenzene)iron(II) hexafluoridophosphate

Hilary A. Jenkins,^a Jason D. Masuda ^a and Adam Piórko ^a ^*

^aDepartment of Chemistry, Saint Mary's University, Halifax, Nova Scotia, Canada B3H 3C3
^*Correspondence e-mail: adam.piorko@smu.ca

(Received 7 July 2009; accepted 16 July 2009; online 22 July 2009)

Both complexed rings in the iron(II) complex cation of the title salt, [Fe(C₅H₅)(C₁₄H₂₀N₂)]PF₆, are almost parallel [dihedral angle between planes = 5.34 (13)°]. Among the C atoms of the complexed arene ring, the quaternary C atoms are located at the longest, albeit unequal, distances from the Fe atom [2.252 (2) and 2.168 (2) Å].

Related literature

For the synthesis of the title compound and related structures, see: Lee et al. (1989 ). For the crystal structures of {(η⁵-Cp)(η⁶-arene) Fe(II)}⁺ salts, see: Nesmeyanov et al. (1977 ); Dubois et al. (1989 ); Piórko et al. (1995 ); Manzur et al. (2000 ); Fuentealba et al. (2007 ); Manzur et al. (2009 ) and literature cited therein.

Experimental

Crystal data

[Fe(C₅H₅)(C₁₄H₂₀N₂)]PF₆
M_r = 482.23
Triclinic, $[P \overline 1]$
a = 9.7303 (6) Å
b = 10.6021 (6) Å
c = 10.6548 (6) Å
α = 93.845 (1)°
β = 113.259 (1)°
γ = 95.822 (1)°
V = 997.7 (1) Å³
Z = 2
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 223 K
0.23 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.742, T_max = 0.866
7374 measured reflections
3501 independent reflections
2493 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.080
S = 0.92
3501 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028116/si2188sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028116/si2188Isup2.hkl

checkCIF report

Comment top

The title compound, along with similar mono- and/or di-N-butylamino- and cyano-arenes complexed with a cyclopentadienyliron(II) moiety, were reported in the study of nucleophilic aromatic mono- and di-substitution reactions using 1,2-, 1,3-, and 1,4-dichlorobenzene FeCp complexes (Lee et al., 1989). The ORTEP of the title compound is shown in Figure 1. The two aromatic rings are not planar, with an angle of 5.34 (13)° between the planes formed by C1···C6 and C21···C25. This is the largest value among those reported previously by our group, although lower than the values 7° reported for 1,1'-trimethylenebenzene-CpFe cation (Nesmeyanov et al., 1977), and 5.4° reported for hexaethylbenzene-CpFe complex (Dubois et al., 1989). No standard uncertainties were given by these authors.

The Fe ion is located at the distances 1.6601 (12) Å from the Cp and 1.5680 (11) Å from the phenyl ring, and these values are close to those reported in the literature for similar complexes (see for example Piórko et al., 1995; Fuentealba et al., 2007; Manzur et al., 2009; and literature cited therein). The Fe - C1 distance at 2.252 (2) Å (where C1 is one of the quaternary carbon atoms in the phenyl ring bonding N1 of pyrrolidinyl substituent), is the longest among the distances Fe to C atoms of this ring. The distance Fe - C2 (where C2 is another quaternary carbon atom of the complexed phenyl ring) is significantly shorter at 2.168 (2) Å. While this second value is typical for an aromatic C atom (in a FeCp or Fe-pentamethylCp complexed phenyl ring) to Fe distance (see for example Piórko et al., 1995; Manzur et al., 2000; Fuentealba et al., 2007; Manzur et al., 2009, and literature cited therein), the Fe - C1 distance is the longest one reported, to the best of our knowledge, for similar iron complexes. In a complexed arene ring, the longest bond between carbon atoms of this ring is found for C1 - C2 quaternary carbon atoms at 1.444 (3) Å, while all other similar bonds are found in the range 1.398 (4) to 1.427 (3) Å. Both nitrogen atoms show similar bond lengths toward aromatic ring carbon atoms [1.377 (3) Å for a ring N1 - C7···C10 and 1.386 (3) Å for a ring N2 - C11···C14], and toward methylene carbon atoms of pyrrolidinyl rings [range 1.453 (3) to 1.467 (3) Å]. One of the pyrrolidinyl rings (N2 - C11···C14) appears to be quite symmetrical and located in and below the plane of the metal-complexed phenyl ring, while another one (N1 - C7···C10) shows distorted both interatomic distances and angles, and is located above the plane of the complexed phenyl ring. The planes defined by the carbon atoms of both pyrrolidinyl rings are tilted with respect to the phenyl ring plane by 32.12(0.17)° for a plane C11···C14 and 29.40(0.13)° for the plane C7···C10.

Related literature top

For the synthesis of the title compound and related structures, see: Lee et al. (1989). For the crystal structures of {(η⁵-Cp)(η⁶-arene) Fe(II)}⁺ salts, see: Nesmeyanov et al. (1977); Dubois et al. (1989); Piórko et al. (1995); Manzur et al. (2000); Fuentealba et al. (2007); Manzur et al. (2009) and literature cited therein.

Experimental top

The title compound was prepared following the method of Lee et al. (1989). A crystal used for data collection was grown by slow evaporation of solvents from a solution of the complex in acetone-diethyl ether-dichloromethane mixture at 280 K.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of the cation showing the labelling of non-H atoms with the thermal ellipsoids shown at 50% probability levels.

(η⁵-Cyclopentadienyl)(η⁶-1,2-dipyrrolidin-1-ylbenzene)iron(II) hexafluoridophosphate top

Crystal data top

[Fe(C₅H₅)(C₁₄H₂₀N₂)]PF₆	Z = 2
M_r = 482.23	F(000) = 496
Triclinic, P1	D_x = 1.605 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7303 (6) Å	Cell parameters from 2668 reflections
b = 10.6021 (6) Å	θ = 23.7–2.8°
c = 10.6548 (6) Å	µ = 0.90 mm⁻¹
α = 93.845 (1)°	T = 223 K
β = 113.259 (1)°	Block, orange
γ = 95.822 (1)°	0.23 × 0.20 × 0.16 mm
V = 997.7 (1) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3501 independent reflections
Radiation source: fine-focus sealed tube	2493 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→11
T_min = 0.742, T_max = 0.866	k = −12→12
7374 measured reflections	l = −12→12

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 0.92	w = 1/[σ²(F_o²) + (0.0452P)²] where P = (F_o² + 2F_c²)/3
3501 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₄H₂₀N₂)]PF₆	γ = 95.822 (1)°
M_r = 482.23	V = 997.7 (1) Å³
Triclinic, P1	Z = 2
a = 9.7303 (6) Å	Mo Kα radiation
b = 10.6021 (6) Å	µ = 0.90 mm⁻¹
c = 10.6548 (6) Å	T = 223 K
α = 93.845 (1)°	0.23 × 0.20 × 0.16 mm
β = 113.259 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3501 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2493 reflections with I > 2σ(I)
T_min = 0.742, T_max = 0.866	R_int = 0.017
7374 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 0.92	Δρ_max = 0.30 e Å⁻³
3501 reflections	Δρ_min = −0.21 e Å⁻³
262 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Fe1	0.67408 (4)	0.24243 (4)	0.77597 (4)	0.03565 (13)
N1	0.3474 (2)	0.07175 (19)	0.7496 (2)	0.0355 (5)
N2	0.3557 (2)	0.34299 (19)	0.7376 (2)	0.0369 (5)
C1	0.4793 (3)	0.1542 (2)	0.8193 (2)	0.0352 (6)
C2	0.4827 (3)	0.2905 (2)	0.8161 (2)	0.0346 (6)
C3	0.6194 (3)	0.3704 (3)	0.8986 (3)	0.0434 (7)
H3A	0.6279	0.4618	0.8844	0.052*
C4	0.7521 (3)	0.3211 (3)	0.9780 (3)	0.0512 (8)
H4A	0.8495	0.3787	1.0197	0.061*
C5	0.7520 (3)	0.1888 (3)	0.9703 (3)	0.0493 (7)
H5A	0.8491	0.1539	1.0073	0.059*
C6	0.6191 (3)	0.1074 (3)	0.8890 (3)	0.0425 (7)
H6A	0.6259	0.0167	0.8668	0.051*
C7	0.3512 (3)	−0.0664 (2)	0.7431 (3)	0.0454 (7)
H7A	0.3983	−0.0926	0.8354	0.055*
H7B	0.4065	−0.0930	0.6886	0.055*
C8	0.1851 (3)	−0.1220 (3)	0.6735 (3)	0.0562 (8)
H8A	0.1530	−0.1386	0.5737	0.067*
H8B	0.1661	−0.2020	0.7087	0.067*
C9	0.1023 (3)	−0.0212 (3)	0.7086 (4)	0.0620 (9)
H9A	0.0186	−0.0044	0.6254	0.074*
H9B	0.0612	−0.0498	0.7739	0.074*
C10	0.2115 (3)	0.0940 (3)	0.7695 (4)	0.0764 (11)
H10A	0.2345	0.1108	0.8677	0.092*
H10B	0.1710	0.1678	0.7244	0.092*
C11	0.3514 (3)	0.4792 (3)	0.7581 (4)	0.0679 (10)
H11A	0.4326	0.5284	0.7420	0.081*
H11B	0.3617	0.5053	0.8517	0.081*
C12	0.2003 (4)	0.4983 (3)	0.6547 (4)	0.0713 (10)
H12A	0.1281	0.5017	0.6976	0.086*
H12B	0.2075	0.5782	0.6149	0.086*
C13	0.1514 (4)	0.3865 (3)	0.5463 (4)	0.0756 (11)
H13A	0.1370	0.4149	0.4569	0.091*
H13B	0.0561	0.3390	0.5387	0.091*
C14	0.2751 (3)	0.3043 (3)	0.5904 (3)	0.0631 (9)
H14A	0.2333	0.2137	0.5718	0.076*
H14B	0.3419	0.3198	0.5425	0.076*
C21	0.8544 (3)	0.2220 (4)	0.7290 (3)	0.0636 (9)
H21A	0.9544	0.2032	0.7924	0.076*
C22	0.7286 (4)	0.1314 (3)	0.6439 (3)	0.0589 (9)
H22A	0.7238	0.0373	0.6360	0.071*
C23	0.6132 (4)	0.2020 (4)	0.5693 (3)	0.0625 (9)
H23A	0.5112	0.1653	0.5009	0.075*
C24	0.6654 (5)	0.3286 (4)	0.6074 (4)	0.0705 (10)
H24A	0.6073	0.3993	0.5715	0.085*
C25	0.8119 (5)	0.3425 (3)	0.7035 (4)	0.0712 (10)
H25A	0.8767	0.4249	0.7479	0.085*
P1	0.22457 (8)	0.25827 (7)	0.16756 (8)	0.0460 (2)
F1	0.3570 (2)	0.2424 (2)	0.1210 (2)	0.1058 (8)
F2	0.1610 (2)	0.35070 (18)	0.0551 (2)	0.0988 (7)
F3	0.2889 (2)	0.16555 (17)	0.2805 (2)	0.1010 (8)
F4	0.0910 (2)	0.27354 (19)	0.2133 (2)	0.0860 (6)
F5	0.12317 (19)	0.14086 (16)	0.05954 (19)	0.0766 (6)
F6	0.32525 (19)	0.37579 (15)	0.27729 (18)	0.0713 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0302 (2)	0.0442 (3)	0.0345 (2)	0.00790 (17)	0.01440 (17)	0.00601 (17)
N1	0.0326 (12)	0.0336 (12)	0.0445 (13)	0.0067 (10)	0.0194 (11)	0.0058 (10)
N2	0.0322 (12)	0.0343 (13)	0.0428 (13)	0.0092 (10)	0.0131 (10)	0.0007 (10)
C1	0.0345 (15)	0.0473 (17)	0.0299 (14)	0.0096 (13)	0.0180 (12)	0.0070 (12)
C2	0.0329 (15)	0.0423 (16)	0.0321 (14)	0.0044 (12)	0.0177 (12)	0.0008 (12)
C3	0.0415 (17)	0.0507 (17)	0.0375 (15)	0.0010 (14)	0.0185 (14)	−0.0051 (13)
C4	0.0342 (16)	0.080 (2)	0.0318 (16)	−0.0004 (16)	0.0086 (13)	−0.0041 (15)
C5	0.0366 (17)	0.075 (2)	0.0382 (16)	0.0164 (16)	0.0132 (14)	0.0172 (16)
C6	0.0389 (16)	0.0540 (18)	0.0416 (16)	0.0140 (14)	0.0203 (14)	0.0163 (14)
C7	0.0524 (18)	0.0412 (17)	0.0498 (17)	0.0138 (14)	0.0257 (15)	0.0100 (14)
C8	0.060 (2)	0.0476 (19)	0.060 (2)	−0.0034 (16)	0.0261 (17)	0.0046 (16)
C9	0.0458 (18)	0.0486 (19)	0.093 (3)	0.0076 (16)	0.0270 (18)	0.0188 (18)
C10	0.0490 (19)	0.060 (2)	0.132 (3)	−0.0054 (17)	0.056 (2)	−0.015 (2)
C11	0.052 (2)	0.049 (2)	0.088 (3)	0.0189 (16)	0.0138 (19)	−0.0108 (18)
C12	0.065 (2)	0.056 (2)	0.097 (3)	0.0278 (18)	0.031 (2)	0.015 (2)
C13	0.067 (2)	0.067 (2)	0.074 (2)	0.0283 (19)	0.0037 (19)	0.009 (2)
C14	0.054 (2)	0.071 (2)	0.0473 (19)	0.0312 (17)	−0.0009 (16)	−0.0007 (17)
C21	0.0356 (18)	0.113 (3)	0.056 (2)	0.0284 (19)	0.0284 (16)	0.017 (2)
C22	0.087 (3)	0.0439 (19)	0.071 (2)	0.0201 (18)	0.056 (2)	0.0065 (17)
C23	0.053 (2)	0.101 (3)	0.0357 (17)	0.009 (2)	0.0230 (16)	−0.0054 (18)
C24	0.093 (3)	0.080 (3)	0.072 (2)	0.039 (2)	0.058 (2)	0.035 (2)
C25	0.086 (3)	0.061 (2)	0.090 (3)	−0.009 (2)	0.067 (2)	−0.002 (2)
P1	0.0372 (4)	0.0382 (4)	0.0523 (5)	0.0053 (3)	0.0078 (4)	0.0025 (4)
F1	0.0534 (12)	0.1385 (19)	0.1172 (18)	−0.0023 (12)	0.0375 (12)	−0.0366 (15)
F2	0.1071 (17)	0.0761 (14)	0.0849 (15)	0.0096 (12)	0.0053 (13)	0.0378 (12)
F3	0.1097 (17)	0.0581 (12)	0.0898 (15)	0.0137 (11)	−0.0105 (13)	0.0263 (11)
F4	0.0559 (12)	0.1074 (16)	0.0916 (15)	−0.0012 (11)	0.0342 (11)	−0.0184 (12)
F5	0.0623 (12)	0.0644 (12)	0.0777 (13)	−0.0119 (9)	0.0115 (10)	−0.0220 (10)
F6	0.0672 (12)	0.0488 (10)	0.0784 (13)	−0.0098 (9)	0.0158 (10)	−0.0095 (9)

Geometric parameters (Å, º) top

Fe1—C22	2.035 (3)	C9—C10	1.459 (4)
Fe1—C21	2.032 (3)	C9—H9A	0.9800
Fe1—C25	2.039 (3)	C9—H9B	0.9800
Fe1—C23	2.044 (3)	C10—H10A	0.9800
Fe1—C24	2.046 (3)	C10—H10B	0.9800
Fe1—C5	2.047 (3)	C11—C12	1.492 (4)
Fe1—C4	2.061 (3)	C11—H11A	0.9800
Fe1—C3	2.071 (3)	C11—H11B	0.9800
Fe1—C6	2.090 (2)	C12—C13	1.495 (4)
Fe1—C2	2.168 (2)	C12—H12A	0.9800
Fe1—C1	2.252 (2)	C12—H12B	0.9800
N1—C1	1.377 (3)	C13—C14	1.500 (4)
N1—C10	1.458 (3)	C13—H13A	0.9800
N1—C7	1.467 (3)	C13—H13B	0.9800
N2—C2	1.386 (3)	C14—H14A	0.9800
N2—C11	1.453 (3)	C14—H14B	0.9800
N2—C14	1.456 (3)	C21—C25	1.394 (4)
C1—C6	1.427 (3)	C21—C22	1.418 (4)
C1—C2	1.444 (3)	C21—H21A	0.9900
C2—C3	1.417 (3)	C22—C23	1.414 (4)
C3—C4	1.411 (4)	C22—H22A	0.9900
C3—H3A	0.9900	C23—C24	1.361 (4)
C4—C5	1.400 (4)	C23—H23A	0.9900
C4—H4A	0.9900	C24—C25	1.374 (5)
C5—C6	1.398 (4)	C24—H24A	0.9900
C5—H5A	0.9900	C25—H25A	0.9900
C6—H6A	0.9900	P1—F1	1.572 (2)
C7—C8	1.520 (4)	P1—F2	1.5731 (19)
C7—H7A	0.9800	P1—F4	1.5762 (19)
C7—H7B	0.9800	P1—F3	1.5791 (19)
C8—C9	1.514 (4)	P1—F5	1.5841 (17)
C8—H8A	0.9800	P1—F6	1.5910 (17)
C8—H8B	0.9800

C22—Fe1—C21	40.80 (12)	C1—C6—H6A	118.5
C22—Fe1—C25	67.36 (12)	Fe1—C6—H6A	118.5
C21—Fe1—C25	40.05 (13)	N1—C7—C8	103.2 (2)
C22—Fe1—C23	40.55 (12)	N1—C7—H7A	111.1
C21—Fe1—C23	67.63 (12)	C8—C7—H7A	111.1
C25—Fe1—C23	66.04 (14)	N1—C7—H7B	111.1
C22—Fe1—C24	67.07 (13)	C8—C7—H7B	111.1
C21—Fe1—C24	67.07 (13)	H7A—C7—H7B	109.1
C25—Fe1—C24	39.29 (13)	C9—C8—C7	104.9 (2)
C23—Fe1—C24	38.88 (12)	C9—C8—H8A	110.8
C22—Fe1—C5	112.92 (13)	C7—C8—H8A	110.8
C21—Fe1—C5	100.20 (12)	C9—C8—H8B	110.8
C25—Fe1—C5	122.30 (15)	C7—C8—H8B	110.8
C23—Fe1—C5	150.64 (14)	H8A—C8—H8B	108.8
C24—Fe1—C5	161.28 (15)	C10—C9—C8	107.1 (2)
C22—Fe1—C4	142.85 (13)	C10—C9—H9A	110.3
C21—Fe1—C4	108.64 (12)	C8—C9—H9A	110.3
C25—Fe1—C4	103.36 (13)	C10—C9—H9B	110.3
C23—Fe1—C4	167.81 (14)	C8—C9—H9B	110.3
C24—Fe1—C4	128.99 (15)	H9A—C9—H9B	108.6
C5—Fe1—C4	39.85 (11)	C9—C10—N1	106.9 (2)
C22—Fe1—C3	174.17 (12)	C9—C10—H10A	110.3
C21—Fe1—C3	137.04 (13)	N1—C10—H10A	110.3
C25—Fe1—C3	107.72 (12)	C9—C10—H10B	110.3
C23—Fe1—C3	135.23 (13)	N1—C10—H10B	110.3
C24—Fe1—C3	107.17 (13)	H10A—C10—H10B	108.6
C5—Fe1—C3	72.16 (11)	N2—C11—C12	104.5 (2)
C4—Fe1—C3	39.95 (10)	N2—C11—H11A	110.9
C22—Fe1—C6	101.81 (11)	C12—C11—H11A	110.9
C21—Fe1—C6	117.43 (12)	N2—C11—H11B	110.9
C25—Fe1—C6	155.33 (14)	C12—C11—H11B	110.9
C23—Fe1—C6	120.86 (13)	H11A—C11—H11B	108.9
C24—Fe1—C6	158.35 (15)	C13—C12—C11	106.0 (2)
C5—Fe1—C6	39.48 (10)	C13—C12—H12A	110.5
C4—Fe1—C6	71.30 (11)	C11—C12—H12A	110.5
C3—Fe1—C6	83.94 (11)	C13—C12—H12B	110.5
C22—Fe1—C2	142.09 (12)	C11—C12—H12B	110.5
C21—Fe1—C2	171.95 (12)	H12A—C12—H12B	108.7
C25—Fe1—C2	131.90 (13)	C12—C13—C14	106.3 (3)
C23—Fe1—C2	110.32 (11)	C12—C13—H13A	110.5
C24—Fe1—C2	106.23 (12)	C14—C13—H13A	110.5
C5—Fe1—C2	85.14 (10)	C12—C13—H13B	110.5
C4—Fe1—C2	71.66 (10)	C14—C13—H13B	110.5
C3—Fe1—C2	38.97 (9)	H13A—C13—H13B	108.7
C6—Fe1—C2	70.48 (10)	N2—C14—C13	104.1 (2)
C22—Fe1—C1	114.95 (11)	N2—C14—H14A	110.9
C21—Fe1—C1	149.61 (13)	C13—C14—H14A	110.9
C25—Fe1—C1	166.39 (14)	N2—C14—H14B	110.9
C23—Fe1—C1	106.37 (11)	C13—C14—H14B	110.9
C24—Fe1—C1	127.86 (14)	H14A—C14—H14B	109.0
C5—Fe1—C1	70.06 (10)	C25—C21—C22	106.9 (3)
C4—Fe1—C1	82.71 (10)	C25—C21—Fe1	70.24 (17)
C3—Fe1—C1	69.04 (10)	C22—C21—Fe1	69.70 (16)
C6—Fe1—C1	38.16 (9)	C25—C21—H21A	126.5
C2—Fe1—C1	38.09 (9)	C22—C21—H21A	126.5
C1—N1—C10	119.5 (2)	Fe1—C21—H21A	126.5
C1—N1—C7	119.5 (2)	C21—C22—C23	106.5 (3)
C10—N1—C7	107.0 (2)	C21—C22—Fe1	69.50 (16)
C2—N2—C11	120.5 (2)	C23—C22—Fe1	70.05 (16)
C2—N2—C14	121.6 (2)	C21—C22—H22A	126.7
C11—N2—C14	106.2 (2)	C23—C22—H22A	126.7
N1—C1—C6	121.1 (2)	Fe1—C22—H22A	126.7
N1—C1—C2	121.1 (2)	C24—C23—C22	108.7 (3)
C6—C1—C2	117.7 (2)	C24—C23—Fe1	70.64 (18)
N1—C1—Fe1	137.22 (17)	C22—C23—Fe1	69.40 (16)
C6—C1—Fe1	64.79 (13)	C24—C23—H23A	125.7
C2—C1—Fe1	67.82 (13)	C22—C23—H23A	125.7
N2—C2—C3	120.3 (2)	Fe1—C23—H23A	125.7
N2—C2—C1	121.6 (2)	C23—C24—C25	108.9 (3)
C3—C2—C1	118.1 (2)	C23—C24—Fe1	70.48 (18)
N2—C2—Fe1	131.77 (17)	C25—C24—Fe1	70.11 (19)
C3—C2—Fe1	66.82 (14)	C23—C24—H24A	125.5
C1—C2—Fe1	74.09 (14)	C25—C24—H24A	125.5
C4—C3—C2	122.3 (3)	Fe1—C24—H24A	125.5
C4—C3—Fe1	69.64 (15)	C24—C25—C21	109.0 (3)
C2—C3—Fe1	74.21 (14)	C24—C25—Fe1	70.60 (19)
C4—C3—H3A	118.2	C21—C25—Fe1	69.71 (17)
C2—C3—H3A	118.2	C24—C25—H25A	125.5
Fe1—C3—H3A	118.2	C21—C25—H25A	125.5
C5—C4—C3	119.2 (3)	Fe1—C25—H25A	125.5
C5—C4—Fe1	69.55 (16)	F1—P1—F2	89.96 (13)
C3—C4—Fe1	70.42 (15)	F1—P1—F4	179.60 (12)
C5—C4—H4A	119.5	F2—P1—F4	89.95 (12)
C3—C4—H4A	119.5	F1—P1—F3	89.87 (13)
Fe1—C4—H4A	119.5	F2—P1—F3	179.82 (14)
C6—C5—C4	119.7 (3)	F4—P1—F3	90.22 (12)
C6—C5—Fe1	71.92 (15)	F1—P1—F5	90.17 (11)
C4—C5—Fe1	70.60 (16)	F2—P1—F5	89.60 (11)
C6—C5—H5A	119.6	F4—P1—F5	89.45 (10)
C4—C5—H5A	119.6	F3—P1—F5	90.45 (10)
Fe1—C5—H5A	119.6	F1—P1—F6	90.50 (11)
C5—C6—C1	122.2 (3)	F2—P1—F6	90.75 (10)
C5—C6—Fe1	68.60 (15)	F4—P1—F6	89.89 (10)
C1—C6—Fe1	77.05 (15)	F3—P1—F6	89.20 (10)
C5—C6—H6A	118.5	F5—P1—F6	179.25 (12)

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₄H₂₀N₂)]PF₆
M_r	482.23
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	9.7303 (6), 10.6021 (6), 10.6548 (6)
α, β, γ (°)	93.845 (1), 113.259 (1), 95.822 (1)
V (Å³)	997.7 (1)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.23 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.742, 0.866
No. of measured, independent and observed [I > 2σ(I)] reflections	7374, 3501, 2493
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.080, 0.92
No. of reflections	3501
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.21

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Acknowledgements

The authors thank Saint Mary's University for financial support.

References

Bruker (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dubois, R. H., Zaworotko, M. J. & White, P. S. (1989). J. Organomet. Chem. 362, 155–161. CSD CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Fuentealba, M., Toupet, L., Manzur, C., Carrillo, D., Ledoux-Rak, I. & Hamon, J.-R. (2007). J. Organomet. Chem. 692, 1099–1109. Web of Science CSD CrossRef CAS Google Scholar
Lee, C. C., Zhang, C. H., Abd-El-Aziz, A. S., Piórko, A. & Sutherland, R. G. (1989). J. Organomet. Chem. 364, 217–229. CrossRef CAS Web of Science Google Scholar
Manzur, C., Baeza, E., Millan, L., Fuentealba, M., Hamon, P., Hamon, J.-R., Boys, D. & Carrillo, D. (2000). J. Organomet. Chem. 608, 126–132. Web of Science CSD CrossRef CAS Google Scholar
Manzur, C., Millan, L., Fuentealba, M., Trujillo, A. & Carrillo, D. (2009). J. Organomet. Chem. 694, 2043–2046. Web of Science CSD CrossRef CAS Google Scholar
Nesmeyanov, A. N., Tolstaya, M. V., Rybinskaya, M. I., Shul'pin, G. B., Bokii, N. G., Batsanov, A. S. & Struchkov, Yu. T. (1977). J. Organomet. Chem. 142, 89–93. CSD CrossRef CAS Web of Science Google Scholar
Piórko, A., Christie, S. & Zaworotko, M. J. (1995). Acta Cryst. C51, 26–29. CSD CrossRef Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.