Dicarbon­yl(η⁵-cyclo­penta­dien­yl)(1-phenyl-3,4-dimethyl­phospho­le)iron(II) tetra­fluoro­borate

The cation of the title compound, C₁₉H₁₈FeO₂P⁺·BF₄⁻ or [Fe(C₅H₅)(C₁₂H₁₃P)(CO)₂]BF₄, features a typical half-sandwich-type structure with four ligands roughly giving a tetra­hedral coordination of the Fe ion.

Key indicators

• Single-crystal X-ray study
• T = 290 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.062
• wR factor = 0.126
• Data-to-parameter ratio = 22.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          2
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.48 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C17
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         Fe
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         B1

Alert level G
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Kuma Diffraction, 2000); cell refinement: CrysAlis RED (Kuma Diffraction, 2000); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: SHELXL97.

Dicarbonyl(η⁵-cyclopentadienyl)-1-phenyl-3,4-dimethylphospholeiron(II) tetrafluoroborate

Crystal data

[Fe(C5H5)(CO)2(C12H13P)]BF4	F(000) = 920
Mr = 451.96	Dx = 1.480 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3527 reflections
a = 8.6625 (9) Å	θ = 5.1–17.1°
b = 17.1238 (18) Å	µ = 0.87 mm^−1
c = 14.0690 (15) Å	T = 290 K
β = 103.588 (11)°	Isometric, yellow
V = 2028.5 (4) Å^3	0.48 × 0.40 × 0.36 mm
Z = 4

Data collection

Stoe STADI CCD diffractometer	3529 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
Graphite monochromator	θmax = 30.0°, θmin = 3.8°
ω scans	h = −10→12
29261 measured reflections	k = −24→24
5857 independent reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.02P)^2 + 3P] where P = (Fo^2 + 2Fc^2)/3
5857 reflections	(Δ/σ)max = 0.003
265 parameters	Δρmax = 0.61 e Å^−3
0 restraints	Δρmin = −0.54 e Å^−3

Special details

Experimental. Diffraction: A single-crystal of the title compound was mounted on a Stoe four-circle diffractometer equipped with a CCD-detector (Stadi-CCD). For the data collection 21 omega-scans (1.0 °) with different chi, phi and 2theta settings and a detector to crystal distance of 80 mm were performed. Integration procedures using variable and intensity dependant integration masks and integration width of 1.00 ° yielded a data completeness of more than 99.0% up to a Bragg angle of 60° two-theta.

1H NMR (200?MHz, D6-acetone): δ 7.73 (m, 2 H, Ph), 7.57 (m, 3 H, Ph), 7.06 (dq,2JHP = 36.2?Hz, 4JHH = 0.9?Hz, 2 H, α-H), 5.26 (d, 3JHP = 1.9?Hz, 5 H, Cp), 2.25 (dd, 4JHP = 1.6?Hz, 4JHH = 0.9?Hz, 6 H, Me); 31P NMR (81?MHz, D6-acetone): δ = 58.4 (s).

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe	0.18235 (5)	0.12435 (3)	0.37013 (3)	0.04598 (14)
P	0.30219 (9)	0.21270 (5)	0.47810 (5)	0.04006 (18)
O1	0.1949 (4)	0.00638 (17)	0.5208 (2)	0.0868 (9)
O2	0.4842 (4)	0.0810 (2)	0.3271 (2)	0.0967 (10)
C1	0.1924 (4)	0.0529 (2)	0.4622 (3)	0.0581 (9)
C2	0.3659 (5)	0.0985 (2)	0.3444 (3)	0.0620 (9)
C3	0.3226 (4)	0.3086 (2)	0.4345 (3)	0.0525 (8)
H3	0.373 (4)	0.3199 (18)	0.390 (2)	0.042 (9)*
C4	0.2491 (4)	0.3598 (2)	0.4800 (3)	0.0589 (9)
C5	0.1762 (4)	0.3239 (2)	0.5550 (2)	0.0575 (9)
C6	0.1973 (4)	0.2473 (2)	0.5647 (2)	0.0501 (8)
H6	0.167 (4)	0.216 (2)	0.609 (2)	0.055 (10)*
C9	0.4966 (3)	0.18231 (19)	0.5473 (2)	0.0461 (7)
C10	0.6320 (3)	0.2093 (2)	0.5217 (2)	0.0721 (11)
H10	0.6238	0.2423	0.4682	0.087*
C11	0.7798 (3)	0.1868 (2)	0.5768 (2)	0.1041 (19)
H11	0.8711	0.2059	0.5609	0.125*
C12	0.7928 (6)	0.1375 (4)	0.6531 (4)	0.112 (2)
H12	0.8928	0.1221	0.6884	0.134*
C13	0.6602 (6)	0.1099 (3)	0.6790 (3)	0.0902 (16)
H13	0.6702	0.0764	0.7322	0.108*
C14	0.5101 (4)	0.1320 (2)	0.6254 (2)	0.0598 (9)
H14	0.4196	0.1129	0.6421	0.072*
C15	0.0076 (5)	0.2072 (2)	0.3150 (3)	0.0768 (13)
H15	0.0036	0.2570	0.3405	0.096 (15)*
C16	−0.0637 (5)	0.1423 (3)	0.3418 (4)	0.0835 (13)
H16	−0.1234	0.1409	0.3887	0.112 (19)*
C17	−0.0332 (6)	0.0794 (3)	0.2886 (4)	0.0925 (16)
H17	−0.0683	0.0286	0.2935	0.110 (17)*
C18	0.0579 (7)	0.1046 (3)	0.2269 (3)	0.0972 (18)
H18	0.0947	0.0741	0.1822	0.13 (2)*
C19	0.0861 (6)	0.1870 (3)	0.2441 (3)	0.0838 (14)
H19	0.1452	0.2198	0.2136	0.084 (13)*
B1	0.7110 (6)	0.3763 (3)	0.3234 (4)	0.0671 (11)
F1	0.6568 (4)	0.30160 (17)	0.3044 (2)	0.1252 (11)
F2	0.8501 (5)	0.3753 (3)	0.3799 (4)	0.231 (3)
F3	0.7074 (5)	0.4054 (2)	0.2328 (3)	0.1636 (17)
F4	0.6028 (3)	0.41855 (17)	0.3576 (2)	0.1045 (9)
C7	0.0856 (5)	0.3717 (3)	0.6139 (3)	0.0932 (15)
H7A	0.1111	0.4259	0.6096	0.140*	0.50
H7B	0.1144	0.3553	0.6810	0.140*	0.50
H7C	−0.0264	0.3642	0.5885	0.140*	0.50
H7D	0.0216	0.3377	0.6431	0.140*	0.50
H7E	0.0184	0.4083	0.5717	0.140*	0.50
H7F	0.1591	0.3995	0.6642	0.140*	0.50
C8	0.2395 (7)	0.4461 (2)	0.4595 (3)	0.0972 (16)
H8A	0.1828	0.4712	0.5020	0.146*	0.50
H8B	0.1848	0.4548	0.3926	0.146*	0.50
H8C	0.3448	0.4673	0.4707	0.146*	0.50
H8D	0.2921	0.4577	0.4082	0.146*	0.50
H8E	0.2901	0.4740	0.5176	0.146*	0.50
H8F	0.1301	0.4615	0.4395	0.146*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe	0.0503 (3)	0.0398 (2)	0.0423 (2)	−0.0011 (2)	−0.00041 (18)	0.00149 (19)
P	0.0370 (4)	0.0414 (4)	0.0397 (4)	−0.0003 (3)	0.0047 (3)	0.0005 (3)
O1	0.111 (2)	0.0679 (18)	0.0755 (18)	−0.0199 (16)	0.0109 (17)	0.0223 (15)
O2	0.090 (2)	0.110 (3)	0.103 (2)	0.008 (2)	0.048 (2)	−0.014 (2)
C1	0.064 (2)	0.0487 (19)	0.058 (2)	−0.0082 (17)	0.0077 (17)	0.0025 (16)
C2	0.076 (3)	0.059 (2)	0.0515 (19)	0.001 (2)	0.0163 (19)	−0.0043 (16)
C3	0.058 (2)	0.0487 (19)	0.0487 (18)	−0.0084 (16)	0.0085 (16)	0.0025 (15)
C4	0.064 (2)	0.0463 (19)	0.0554 (19)	0.0023 (16)	−0.0076 (17)	−0.0071 (15)
C5	0.0473 (19)	0.068 (2)	0.0517 (18)	0.0127 (17)	0.0004 (15)	−0.0151 (17)
C6	0.0372 (17)	0.065 (2)	0.0468 (17)	0.0040 (16)	0.0071 (14)	0.0016 (16)
C9	0.0370 (16)	0.0508 (18)	0.0472 (16)	0.0027 (14)	0.0031 (13)	−0.0123 (14)
C10	0.046 (2)	0.100 (3)	0.072 (2)	−0.003 (2)	0.0158 (18)	−0.015 (2)
C11	0.041 (2)	0.154 (5)	0.113 (4)	0.005 (3)	0.008 (2)	−0.054 (4)
C12	0.060 (3)	0.130 (5)	0.119 (4)	0.042 (3)	−0.035 (3)	−0.057 (4)
C13	0.100 (4)	0.067 (3)	0.076 (3)	0.029 (3)	−0.035 (3)	−0.015 (2)
C14	0.062 (2)	0.0503 (19)	0.0563 (19)	0.0053 (17)	−0.0069 (16)	−0.0039 (16)
C15	0.066 (3)	0.053 (2)	0.088 (3)	0.014 (2)	−0.028 (2)	−0.006 (2)
C16	0.054 (2)	0.096 (4)	0.087 (3)	0.002 (2)	−0.010 (2)	0.002 (3)
C17	0.083 (3)	0.071 (3)	0.096 (4)	−0.017 (3)	−0.033 (3)	0.000 (3)
C18	0.114 (4)	0.105 (4)	0.049 (2)	0.034 (3)	−0.028 (2)	−0.026 (2)
C19	0.082 (3)	0.095 (3)	0.061 (2)	−0.003 (3)	−0.011 (2)	0.037 (2)
B1	0.067 (3)	0.063 (3)	0.070 (3)	0.003 (2)	0.013 (2)	−0.004 (2)
F1	0.158 (3)	0.081 (2)	0.136 (3)	0.0014 (19)	0.034 (2)	−0.0176 (18)
F2	0.112 (3)	0.250 (5)	0.259 (5)	0.059 (3)	−0.097 (3)	−0.118 (4)
F3	0.214 (4)	0.159 (3)	0.155 (3)	0.055 (3)	0.117 (3)	0.053 (3)
F4	0.103 (2)	0.101 (2)	0.121 (2)	0.0061 (16)	0.0488 (17)	−0.0299 (17)
C7	0.079 (3)	0.106 (4)	0.091 (3)	0.035 (3)	0.013 (2)	−0.031 (3)
C8	0.142 (4)	0.043 (2)	0.092 (3)	0.005 (2)	−0.002 (3)	−0.010 (2)

Geometric parameters (Å, º)

Fe—C2	1.768 (4)	C13—H13	0.9300
Fe—C1	1.769 (4)	C14—H14	0.9300
Fe—C19	2.073 (4)	C15—C16	1.367 (6)
Fe—C18	2.078 (4)	C15—C19	1.376 (6)
Fe—C15	2.086 (4)	C15—H15	0.9300
Fe—C17	2.095 (4)	C16—C17	1.371 (7)
Fe—C16	2.097 (4)	C16—H16	0.9300
Fe—P	2.2210 (9)	C17—C18	1.373 (7)
P—C3	1.777 (3)	C17—H17	0.9300
P—C6	1.784 (3)	C18—C19	1.444 (7)
P—C9	1.813 (3)	C18—H18	0.9300
O1—C1	1.143 (4)	C19—H19	0.9300
O2—C2	1.147 (4)	B1—F2	1.279 (5)
C3—C4	1.332 (5)	B1—F4	1.358 (5)
C3—H3	0.87 (3)	B1—F3	1.362 (6)
C4—C5	1.485 (5)	B1—F1	1.367 (5)
C4—C8	1.504 (5)	C7—H7A	0.9600
C5—C6	1.328 (5)	C7—H7B	0.9600
C5—C7	1.509 (5)	C7—H7C	0.9600
C6—H6	0.90 (3)	C7—H7D	0.9600
C9—C14	1.379 (5)	C7—H7E	0.9600
C9—C10	1.384 (4)	C7—H7F	0.9600
C10—C11	1.386 (4)	C8—H8A	0.9600
C10—H10	0.9300	C8—H8B	0.9600
C11—C12	1.349 (7)	C8—H8C	0.9600
C11—H11	0.9300	C8—H8D	0.9600
C12—C13	1.369 (8)	C8—H8E	0.9600
C12—H12	0.9300	C8—H8F	0.9600
C13—C14	1.393 (5)
C2—Fe—C1	94.86 (17)	C15—C16—C17	109.3 (5)
C2—Fe—C19	98.9 (2)	C15—C16—Fe	70.5 (2)
C1—Fe—C19	157.69 (18)	C17—C16—Fe	70.8 (3)
C2—Fe—C18	92.7 (2)	C15—C16—H16	125.4
C1—Fe—C18	121.5 (2)	C17—C16—H16	125.4
C19—Fe—C18	40.71 (19)	Fe—C16—H16	124.9
C2—Fe—C15	134.7 (2)	C18—C17—C16	108.2 (5)
C1—Fe—C15	130.5 (2)	C18—C17—Fe	70.1 (3)
C19—Fe—C15	38.64 (18)	C16—C17—Fe	71.0 (2)
C18—Fe—C15	65.43 (18)	C18—C17—H17	125.9
C2—Fe—C17	121.6 (2)	C16—C17—H17	125.9
C1—Fe—C17	91.78 (19)	Fe—C17—H17	124.6
C19—Fe—C17	66.0 (2)	C17—C18—C19	107.5 (5)
C18—Fe—C17	38.4 (2)	C17—C18—Fe	71.5 (2)
C15—Fe—C17	64.55 (18)	C19—C18—Fe	69.5 (2)
C2—Fe—C16	157.00 (19)	C17—C18—H18	126.3
C1—Fe—C16	96.50 (19)	C19—C18—H18	126.3
C19—Fe—C16	64.8 (2)	Fe—C18—H18	124.4
C18—Fe—C16	64.3 (2)	C15—C19—C18	105.9 (4)
C15—Fe—C16	38.14 (17)	C15—C19—Fe	71.2 (2)
C17—Fe—C16	38.19 (18)	C18—C19—Fe	69.8 (2)
C2—Fe—P	90.73 (12)	C15—C19—H19	127.1
C1—Fe—P	92.04 (11)	C18—C19—H19	127.1
C19—Fe—P	105.18 (15)	Fe—C19—H19	123.6
C18—Fe—P	145.79 (17)	F2—B1—F4	114.5 (4)
C15—Fe—P	88.47 (12)	F2—B1—F3	113.4 (5)
C17—Fe—P	146.92 (17)	F4—B1—F3	105.7 (4)
C16—Fe—P	108.74 (15)	F2—B1—F1	109.8 (5)
C3—P—C6	92.14 (18)	F4—B1—F1	109.5 (4)
C3—P—C9	107.19 (16)	F3—B1—F1	103.2 (4)
C6—P—C9	106.64 (14)	C5—C7—H7A	109.5
C3—P—Fe	117.52 (11)	C5—C7—H7B	109.5
C6—P—Fe	117.52 (12)	H7A—C7—H7B	109.5
C9—P—Fe	113.45 (10)	C5—C7—H7C	109.5
O1—C1—Fe	178.3 (3)	H7A—C7—H7C	109.5
O2—C2—Fe	179.3 (4)	H7B—C7—H7C	109.5
C4—C3—P	110.1 (3)	C5—C7—H7D	109.5
C4—C3—H3	126 (2)	H7A—C7—H7D	141.1
P—C3—H3	124 (2)	H7B—C7—H7D	56.3
C3—C4—C5	113.6 (3)	H7C—C7—H7D	56.3
C3—C4—C8	124.4 (4)	C5—C7—H7E	109.5
C5—C4—C8	122.0 (4)	H7A—C7—H7E	56.3
C6—C5—C4	114.3 (3)	H7B—C7—H7E	141.1
C6—C5—C7	123.8 (4)	H7C—C7—H7E	56.3
C4—C5—C7	121.9 (4)	H7D—C7—H7E	109.5
C5—C6—P	109.7 (3)	C5—C7—H7F	109.5
C5—C6—H6	127 (2)	H7A—C7—H7F	56.3
P—C6—H6	123 (2)	H7B—C7—H7F	56.3
C14—C9—C10	119.8 (3)	H7C—C7—H7F	141.1
C14—C9—P	120.1 (3)	H7D—C7—H7F	109.5
C10—C9—P	120.1 (3)	H7E—C7—H7F	109.5
C11—C10—C9	119.3 (2)	C4—C8—H8A	109.5
C11—C10—H10	120.4	C4—C8—H8B	109.5
C9—C10—H10	120.4	H8A—C8—H8B	109.5
C12—C11—C10	120.8 (3)	C4—C8—H8C	109.5
C12—C11—H11	119.6	H8A—C8—H8C	109.5
C10—C11—H11	119.6	H8B—C8—H8C	109.5
C11—C12—C13	120.7 (4)	C4—C8—H8D	109.5
C11—C12—H12	119.7	H8A—C8—H8D	141.1
C13—C12—H12	119.7	H8B—C8—H8D	56.3
C12—C13—C14	119.7 (5)	H8C—C8—H8D	56.3
C12—C13—H13	120.1	C4—C8—H8E	109.5
C14—C13—H13	120.1	H8A—C8—H8E	56.3
C9—C14—C13	119.7 (4)	H8B—C8—H8E	141.1
C9—C14—H14	120.2	H8C—C8—H8E	56.3
C13—C14—H14	120.2	H8D—C8—H8E	109.5
C16—C15—C19	109.2 (4)	C4—C8—H8F	109.5
C16—C15—Fe	71.3 (2)	H8A—C8—H8F	56.3
C19—C15—Fe	70.1 (2)	H8B—C8—H8F	56.3
C16—C15—H15	125.4	H8C—C8—H8F	141.1
C19—C15—H15	125.4	H8D—C8—H8F	109.5
Fe—C15—H15	124.7	H8E—C8—H8F	109.5
C2—Fe—P—C3	89.22 (19)	Fe—C15—C16—C17	−60.5 (3)
C1—Fe—P—C3	−175.89 (19)	C19—C15—C16—Fe	60.2 (3)
C19—Fe—P—C3	−10.2 (2)	C2—Fe—C16—C15	−85.0 (6)
C18—Fe—P—C3	−6.7 (4)	C1—Fe—C16—C15	155.8 (3)
C15—Fe—P—C3	−45.5 (2)	C19—Fe—C16—C15	−36.9 (3)
C17—Fe—P—C3	−79.5 (3)	C18—Fe—C16—C15	−82.2 (3)
C16—Fe—P—C3	−78.3 (2)	C17—Fe—C16—C15	−119.6 (5)
C2—Fe—P—C6	−162.18 (18)	P—Fe—C16—C15	61.5 (3)
C1—Fe—P—C6	−67.29 (18)	C2—Fe—C16—C17	34.5 (7)
C19—Fe—P—C6	98.4 (2)	C1—Fe—C16—C17	−84.6 (3)
C18—Fe—P—C6	101.9 (3)	C19—Fe—C16—C17	82.6 (3)
C15—Fe—P—C6	63.2 (2)	C18—Fe—C16—C17	37.3 (3)
C17—Fe—P—C6	29.1 (3)	C15—Fe—C16—C17	119.6 (5)
C16—Fe—P—C6	30.3 (2)	P—Fe—C16—C17	−179.0 (3)
C2—Fe—P—C9	−36.88 (17)	C15—C16—C17—C18	−0.2 (5)
C1—Fe—P—C9	58.01 (17)	Fe—C16—C17—C18	−60.5 (3)
C19—Fe—P—C9	−136.3 (2)	C15—C16—C17—Fe	60.3 (3)
C18—Fe—P—C9	−132.8 (3)	C2—Fe—C17—C18	−46.5 (4)
C15—Fe—P—C9	−171.5 (2)	C1—Fe—C17—C18	−143.3 (3)
C17—Fe—P—C9	154.4 (3)	C19—Fe—C17—C18	39.2 (3)
C16—Fe—P—C9	155.6 (2)	C15—Fe—C17—C18	81.9 (3)
C6—P—C3—C4	−2.6 (3)	C16—Fe—C17—C18	118.4 (5)
C9—P—C3—C4	−110.8 (3)	P—Fe—C17—C18	120.2 (4)
Fe—P—C3—C4	120.1 (2)	C2—Fe—C17—C16	−164.9 (3)
P—C3—C4—C5	1.8 (4)	C1—Fe—C17—C16	98.3 (3)
P—C3—C4—C8	−178.6 (3)	C19—Fe—C17—C16	−79.2 (3)
C3—C4—C5—C6	0.5 (4)	C18—Fe—C17—C16	−118.4 (5)
C8—C4—C5—C6	−179.2 (3)	C15—Fe—C17—C16	−36.5 (3)
C3—C4—C5—C7	−179.2 (3)	P—Fe—C17—C16	1.8 (5)
C8—C4—C5—C7	1.1 (5)	C16—C17—C18—C19	0.6 (5)
C4—C5—C6—P	−2.4 (4)	Fe—C17—C18—C19	−60.4 (3)
C7—C5—C6—P	177.3 (3)	C16—C17—C18—Fe	61.1 (3)
C3—P—C6—C5	2.9 (3)	C2—Fe—C18—C17	141.8 (3)
C9—P—C6—C5	111.5 (3)	C1—Fe—C18—C17	44.4 (4)
Fe—P—C6—C5	−119.9 (2)	C19—Fe—C18—C17	−117.6 (5)
C3—P—C9—C14	148.9 (3)	C15—Fe—C18—C17	−79.4 (3)
C6—P—C9—C14	51.2 (3)	C16—Fe—C18—C17	−37.1 (3)
Fe—P—C9—C14	−79.7 (3)	P—Fe—C18—C17	−122.9 (4)
C3—P—C9—C10	−31.3 (3)	C2—Fe—C18—C19	−100.6 (3)
C6—P—C9—C10	−129.0 (3)	C1—Fe—C18—C19	162.1 (3)
Fe—P—C9—C10	100.1 (2)	C15—Fe—C18—C19	38.2 (3)
C14—C9—C10—C11	−1.6 (4)	C17—Fe—C18—C19	117.6 (5)
P—C9—C10—C11	178.66 (11)	C16—Fe—C18—C19	80.5 (3)
C9—C10—C11—C12	1.6 (3)	P—Fe—C18—C19	−5.3 (5)
C10—C11—C12—C13	−1.3 (6)	C16—C15—C19—C18	0.7 (4)
C11—C12—C13—C14	0.8 (7)	Fe—C15—C19—C18	61.6 (3)
C10—C9—C14—C13	1.1 (5)	C16—C15—C19—Fe	−60.9 (3)
P—C9—C14—C13	−179.1 (3)	C17—C18—C19—C15	−0.8 (5)
C12—C13—C14—C9	−0.8 (6)	Fe—C18—C19—C15	−62.5 (3)
C2—Fe—C15—C16	146.8 (3)	C17—C18—C19—Fe	61.7 (3)
C1—Fe—C15—C16	−32.3 (4)	C2—Fe—C19—C15	−160.6 (3)
C19—Fe—C15—C16	119.4 (4)	C1—Fe—C19—C15	71.9 (6)
C18—Fe—C15—C16	79.1 (3)	C18—Fe—C19—C15	115.6 (4)
C17—Fe—C15—C16	36.6 (3)	C17—Fe—C19—C15	78.6 (3)
P—Fe—C15—C16	−123.7 (3)	C16—Fe—C19—C15	36.5 (3)
C2—Fe—C15—C19	27.4 (4)	P—Fe—C19—C15	−67.4 (3)
C1—Fe—C15—C19	−151.7 (3)	C2—Fe—C19—C18	83.7 (4)
C18—Fe—C15—C19	−40.3 (3)	C1—Fe—C19—C18	−43.8 (7)
C17—Fe—C15—C19	−82.8 (3)	C15—Fe—C19—C18	−115.6 (4)
C16—Fe—C15—C19	−119.4 (4)	C17—Fe—C19—C18	−37.0 (3)
P—Fe—C15—C19	116.9 (3)	C16—Fe—C19—C18	−79.2 (3)
C19—C15—C16—C17	−0.3 (5)	P—Fe—C19—C18	176.9 (3)