[2-(Diphenyl­phosphino)phenyl­imino­meth­yl]ferrocene

The title compound, [Fe(C₅H₅)(C₂₄H₁₉NP)], a new Schiff base containing a ferrocenyl (Fc) group, has been synthesized and characterized structurally. The compound is a trans isomer with the C_Fc—C—N—C linkage almost planar.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.079
• wR factor = 0.192
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level A
TYPE059_ALERT_1_A  _diffrn_reflns_av_R_equivalents is not of type numb.

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         43 Perc.
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C26    -   C27     ..       5.66 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C28    -   C29     ..       5.41 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C9
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C29
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         Fe
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

[2-(Diphenylphosphino)phenyliminomethyl]ferrocene

Crystal data

[Fe(C5H5)(C24H19NP)]	F(000) = 1968
Mr = 473.31	Dx = 1.353 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 13.902 (3) Å	θ = 9–12°
b = 9.3370 (19) Å	µ = 0.73 mm^−1
c = 35.815 (7) Å	T = 293 K
V = 4648.9 (16) Å^3	Needle, red
Z = 8	0.40 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	1939 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 1.1°
Graphite monochromator	h = 0→17
ω/2θ scans	k = 0→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	l = 0→44
Tmin = 0.758, Tmax = 0.930	3 standard reflections every 200 reflections
4553 measured reflections	intensity decay: none
4553 independent reflections

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.192	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 4.5P] where P = (Fo^2 + 2Fc^2)/3
4553 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.27 e Å^−3
48 restraints	Δρmin = −0.31 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃): 3.965 (s, 5H), 4.377 (s, 2H), 4.631 (s, 2H), 7.069 (s, 1H), 7.087 (s, 1H), 7.106 (s, 1H), 7.307 (m, 11H), 8.181 (s, 1H).

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
Fe	0.89610 (7)	0.14778 (10)	0.70454 (3)	0.0528 (3)
P	0.94569 (15)	0.6787 (2)	0.60791 (6)	0.0560 (5)
N	0.8422 (4)	0.4198 (6)	0.61883 (18)	0.0566 (17)
C1	1.0059 (6)	0.8258 (8)	0.5828 (2)	0.060 (2)
C2	1.1000 (7)	0.8265 (10)	0.5726 (3)	0.092 (3)
H2A	1.1383	0.7472	0.5777	0.110*
C3	1.1390 (8)	0.9420 (12)	0.5550 (3)	0.123 (4)
H3A	1.2041	0.9415	0.5491	0.148*
C4	1.0836 (8)	1.0606 (12)	0.5458 (3)	0.110 (3)
H4A	1.1102	1.1377	0.5330	0.132*
C5	0.9904 (8)	1.0609 (10)	0.5558 (3)	0.095 (3)
H5A	0.9523	1.1398	0.5502	0.114*
C6	0.9506 (6)	0.9453 (8)	0.5744 (2)	0.074 (2)
H6A	0.8862	0.9478	0.5814	0.088*
C7	1.0488 (5)	0.5780 (8)	0.6248 (2)	0.0520 (18)
C8	1.0970 (7)	0.6280 (9)	0.6557 (2)	0.077 (2)
H8A	1.0760	0.7125	0.6667	0.093*
C9	1.1745 (8)	0.5588 (11)	0.6708 (3)	0.104 (4)
H9A	1.2044	0.5955	0.6920	0.125*
C10	1.2075 (7)	0.4361 (12)	0.6548 (3)	0.092 (3)
H10A	1.2629	0.3925	0.6639	0.110*
C11	1.1590 (6)	0.3765 (10)	0.6251 (3)	0.086 (3)
H11A	1.1786	0.2893	0.6151	0.103*
C12	1.0804 (6)	0.4481 (9)	0.6102 (2)	0.075 (3)
H12A	1.0480	0.4084	0.5900	0.090*
C13	0.9008 (5)	0.5668 (7)	0.5699 (2)	0.0537 (18)
C14	0.8480 (5)	0.4475 (7)	0.5799 (2)	0.0529 (19)
C15	0.8053 (5)	0.3616 (9)	0.5526 (2)	0.066 (2)
H15A	0.7705	0.2807	0.5594	0.080*
C16	0.8148 (6)	0.3972 (9)	0.5159 (2)	0.076 (3)
H16A	0.7857	0.3403	0.4978	0.091*
C17	0.8661 (6)	0.5144 (10)	0.5052 (2)	0.073 (2)
H17A	0.8718	0.5369	0.4800	0.087*
C18	0.9099 (5)	0.6002 (8)	0.5318 (2)	0.063 (2)
H18A	0.9452	0.6800	0.5245	0.076*
C19	0.8202 (5)	0.2998 (7)	0.6325 (2)	0.055 (2)
H19A	0.8090	0.2234	0.6164	0.066*
C20	0.8118 (5)	0.2767 (7)	0.6723 (2)	0.0510 (19)
C21	0.8567 (5)	0.3548 (7)	0.7014 (2)	0.0563 (18)
H21A	0.9002	0.4366	0.6983	0.068*
C22	0.8267 (5)	0.2984 (8)	0.7349 (2)	0.060 (2)
H22A	0.8458	0.3325	0.7597	0.072*
C23	0.7638 (6)	0.1819 (8)	0.7275 (2)	0.064 (2)
H23A	0.7324	0.1214	0.7463	0.076*
C24	0.7572 (6)	0.1657 (8)	0.6885 (2)	0.063 (2)
H24A	0.7195	0.0934	0.6751	0.076*
C25	0.9417 (7)	−0.0519 (8)	0.6902 (3)	0.086 (3)
H25A	0.9047	−0.1267	0.6775	0.103*
C26	1.0014 (6)	0.0537 (10)	0.6736 (3)	0.079 (3)
H26A	1.0104	0.0668	0.6467	0.095*
C27	1.0419 (6)	0.1384 (9)	0.7010 (3)	0.081 (3)
H27A	1.0851	0.2198	0.6968	0.097*
C28	1.0109 (7)	0.0863 (9)	0.7362 (3)	0.078 (3)
H28A	1.0288	0.1253	0.7606	0.093*
C29	0.9507 (7)	−0.0296 (10)	0.7298 (3)	0.091 (3)
H29A	0.9182	−0.0859	0.7491	0.109*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe	0.0537 (6)	0.0300 (5)	0.0747 (7)	0.0024 (5)	−0.0060 (6)	0.0031 (6)
P	0.0553 (12)	0.0414 (10)	0.0715 (14)	0.0000 (10)	0.0044 (11)	0.0033 (10)
N	0.058 (4)	0.039 (3)	0.074 (5)	−0.006 (3)	0.006 (3)	0.009 (3)
C1	0.057 (4)	0.050 (4)	0.072 (5)	−0.004 (4)	0.001 (4)	0.006 (4)
C2	0.073 (5)	0.085 (5)	0.118 (6)	0.001 (5)	0.019 (5)	0.028 (5)
C3	0.096 (6)	0.108 (6)	0.165 (8)	−0.014 (5)	0.022 (6)	0.049 (6)
C4	0.112 (6)	0.091 (6)	0.125 (7)	−0.015 (5)	0.011 (6)	0.036 (6)
C5	0.105 (6)	0.059 (5)	0.120 (7)	0.000 (5)	−0.004 (6)	0.018 (5)
C6	0.070 (5)	0.052 (4)	0.098 (6)	0.004 (4)	0.001 (4)	0.009 (4)
C7	0.056 (5)	0.050 (4)	0.050 (4)	−0.006 (4)	−0.002 (4)	0.006 (4)
C8	0.089 (6)	0.062 (5)	0.080 (6)	−0.001 (5)	−0.027 (5)	−0.004 (5)
C9	0.131 (10)	0.089 (8)	0.093 (8)	0.001 (7)	−0.046 (7)	−0.008 (7)
C10	0.067 (6)	0.097 (8)	0.111 (8)	0.006 (6)	−0.018 (6)	0.016 (7)
C11	0.070 (6)	0.082 (7)	0.105 (7)	0.025 (5)	−0.004 (6)	−0.001 (6)
C12	0.072 (6)	0.071 (6)	0.081 (6)	0.010 (5)	−0.012 (5)	0.002 (5)
C13	0.051 (4)	0.043 (4)	0.066 (5)	0.003 (4)	0.000 (4)	0.004 (4)
C14	0.045 (4)	0.040 (4)	0.073 (5)	0.006 (4)	0.000 (4)	−0.003 (4)
C15	0.052 (5)	0.061 (5)	0.086 (6)	−0.008 (4)	−0.004 (4)	0.012 (5)
C16	0.087 (7)	0.077 (6)	0.064 (6)	0.004 (5)	−0.018 (5)	−0.008 (5)
C17	0.070 (6)	0.094 (7)	0.053 (5)	−0.003 (5)	−0.001 (4)	0.006 (5)
C18	0.053 (5)	0.064 (5)	0.073 (6)	−0.003 (4)	0.006 (4)	0.009 (4)
C19	0.052 (5)	0.040 (4)	0.074 (6)	−0.002 (4)	−0.015 (4)	0.002 (4)
C20	0.052 (5)	0.028 (4)	0.073 (5)	0.005 (3)	−0.009 (4)	0.007 (4)
C21	0.061 (4)	0.029 (3)	0.079 (5)	−0.002 (4)	−0.007 (4)	0.004 (4)
C22	0.068 (5)	0.046 (4)	0.066 (5)	0.010 (4)	−0.011 (4)	0.000 (4)
C23	0.059 (5)	0.048 (4)	0.083 (6)	0.002 (4)	0.003 (5)	−0.003 (4)
C24	0.056 (5)	0.050 (4)	0.083 (6)	−0.001 (4)	−0.011 (4)	0.015 (4)
C25	0.071 (6)	0.033 (4)	0.153 (10)	0.011 (4)	−0.005 (6)	−0.025 (5)
C26	0.071 (6)	0.078 (6)	0.088 (7)	0.009 (5)	−0.004 (5)	−0.022 (6)
C27	0.056 (5)	0.066 (5)	0.120 (8)	0.000 (5)	0.011 (6)	0.021 (6)
C28	0.078 (6)	0.049 (5)	0.106 (8)	0.013 (5)	−0.031 (6)	−0.008 (5)
C29	0.094 (8)	0.059 (6)	0.119 (9)	0.040 (6)	0.002 (7)	0.028 (6)

Geometric parameters (Å, º)

Fe—C21	2.012 (7)	C11—C12	1.386 (10)
Fe—C24	2.021 (8)	C11—H11A	0.9300
Fe—C22	2.022 (7)	C12—H12A	0.9300
Fe—C27	2.033 (8)	C13—C14	1.381 (9)
Fe—C29	2.033 (8)	C13—C18	1.403 (10)
Fe—C25	2.035 (7)	C14—C15	1.397 (10)
Fe—C26	2.035 (8)	C15—C16	1.360 (10)
Fe—C20	2.039 (7)	C15—H15A	0.9300
Fe—C28	2.039 (8)	C16—C17	1.362 (10)
Fe—C23	2.040 (8)	C16—H16A	0.9300
P—C7	1.818 (7)	C17—C18	1.388 (10)
P—C13	1.826 (7)	C17—H17A	0.9300
P—C1	1.843 (7)	C18—H18A	0.9300
N—C19	1.260 (8)	C19—C20	1.448 (10)
N—C14	1.422 (9)	C19—H19A	0.9300
C1—C2	1.357 (10)	C20—C24	1.409 (9)
C1—C6	1.388 (10)	C20—C21	1.418 (9)
C2—C3	1.362 (12)	C21—C22	1.374 (9)
C2—H2A	0.9300	C21—H21A	0.9800
C3—C4	1.389 (13)	C22—C23	1.420 (9)
C3—H3A	0.9300	C22—H22A	0.9800
C4—C5	1.344 (12)	C23—C24	1.409 (10)
C4—H4A	0.9300	C23—H23A	0.9800
C5—C6	1.383 (11)	C24—H24A	0.9800
C5—H5A	0.9300	C25—C26	1.419 (11)
C6—H6A	0.9300	C25—C29	1.438 (12)
C7—C8	1.373 (9)	C25—H25A	0.9800
C7—C12	1.392 (10)	C26—C27	1.380 (11)
C8—C9	1.369 (11)	C26—H26A	0.9800
C8—H8A	0.9300	C27—C28	1.418 (11)
C9—C10	1.362 (12)	C27—H27A	0.9800
C9—H9A	0.9300	C28—C29	1.387 (11)
C10—C11	1.378 (11)	C28—H28A	0.9800
C10—H10A	0.9300	C29—H29A	0.9800
C21—Fe—C24	69.2 (3)	C11—C12—H12A	119.2
C21—Fe—C22	39.8 (3)	C7—C12—H12A	119.2
C24—Fe—C22	68.8 (3)	C14—C13—C18	118.5 (7)
C21—Fe—C27	108.0 (3)	C14—C13—P	116.8 (6)
C24—Fe—C27	159.7 (4)	C18—C13—P	124.5 (6)
C22—Fe—C27	122.7 (4)	C13—C14—C15	120.6 (8)
C21—Fe—C29	155.3 (4)	C13—C14—N	115.6 (7)
C24—Fe—C29	123.4 (4)	C15—C14—N	123.9 (7)
C22—Fe—C29	120.4 (4)	C16—C15—C14	119.6 (8)
C27—Fe—C29	67.7 (4)	C16—C15—H15A	120.2
C21—Fe—C25	162.0 (4)	C14—C15—H15A	120.2
C24—Fe—C25	107.5 (4)	C15—C16—C17	121.3 (8)
C22—Fe—C25	157.1 (4)	C15—C16—H16A	119.4
C27—Fe—C25	68.5 (4)	C17—C16—H16A	119.4
C29—Fe—C25	41.4 (3)	C16—C17—C18	120.0 (8)
C21—Fe—C26	125.5 (4)	C16—C17—H17A	120.0
C24—Fe—C26	124.6 (4)	C18—C17—H17A	120.0
C22—Fe—C26	159.4 (4)	C17—C18—C13	120.0 (7)
C27—Fe—C26	39.7 (3)	C17—C18—H18A	120.0
C29—Fe—C26	67.8 (4)	C13—C18—H18A	120.0
C25—Fe—C26	40.8 (3)	N—C19—C20	122.3 (7)
C21—Fe—C20	41.0 (3)	N—C19—H19A	118.9
C24—Fe—C20	40.6 (3)	C20—C19—H19A	118.9
C22—Fe—C20	67.6 (3)	C24—C20—C21	108.2 (7)
C27—Fe—C20	124.3 (3)	C24—C20—C19	124.0 (7)
C29—Fe—C20	161.3 (4)	C21—C20—C19	127.8 (7)
C25—Fe—C20	125.2 (4)	C24—C20—Fe	69.0 (4)
C26—Fe—C20	111.1 (3)	C21—C20—Fe	68.5 (4)
C21—Fe—C28	120.9 (3)	C19—C20—Fe	126.8 (5)
C24—Fe—C28	158.2 (4)	C22—C21—C20	108.1 (6)
C22—Fe—C28	105.7 (3)	C22—C21—Fe	70.5 (4)
C27—Fe—C28	40.8 (3)	C20—C21—Fe	70.5 (4)
C29—Fe—C28	39.8 (3)	C22—C21—H21A	126.0
C25—Fe—C28	68.8 (4)	C20—C21—H21A	126.0
C26—Fe—C28	67.6 (4)	Fe—C21—H21A	126.0
C20—Fe—C28	158.5 (3)	C21—C22—C23	108.6 (7)
C21—Fe—C23	68.1 (3)	C21—C22—Fe	69.7 (4)
C24—Fe—C23	40.6 (3)	C23—C22—Fe	70.2 (4)
C22—Fe—C23	40.9 (3)	C21—C22—H22A	125.7
C27—Fe—C23	158.6 (4)	C23—C22—H22A	125.7
C29—Fe—C23	106.5 (4)	Fe—C22—H22A	125.7
C25—Fe—C23	121.7 (4)	C24—C23—C22	107.8 (7)
C26—Fe—C23	159.3 (4)	C24—C23—Fe	69.0 (5)
C20—Fe—C23	67.5 (3)	C22—C23—Fe	68.9 (4)
C28—Fe—C23	121.7 (4)	C24—C23—H23A	126.1
C7—P—C13	102.8 (3)	C22—C23—H23A	126.1
C7—P—C1	101.0 (3)	Fe—C23—H23A	126.1
C13—P—C1	102.5 (3)	C23—C24—C20	107.1 (7)
C19—N—C14	123.8 (7)	C23—C24—Fe	70.4 (5)
C2—C1—C6	118.2 (8)	C20—C24—Fe	70.4 (4)
C2—C1—P	124.9 (7)	C23—C24—H24A	126.4
C6—C1—P	116.9 (6)	C20—C24—H24A	126.4
C1—C2—C3	120.7 (9)	Fe—C24—H24A	126.4
C1—C2—H2A	119.6	C26—C25—C29	105.2 (8)
C3—C2—H2A	119.6	C26—C25—Fe	69.6 (4)
C2—C3—C4	121.5 (10)	C29—C25—Fe	69.2 (4)
C2—C3—H3A	119.3	C26—C25—H25A	127.4
C4—C3—H3A	119.3	C29—C25—H25A	127.4
C5—C4—C3	118.1 (10)	Fe—C25—H25A	127.4
C5—C4—H4A	120.9	C27—C26—C25	109.8 (9)
C3—C4—H4A	120.9	C27—C26—Fe	70.1 (5)
C4—C5—C6	120.9 (10)	C25—C26—Fe	69.6 (5)
C4—C5—H5A	119.6	C27—C26—H26A	125.1
C6—C5—H5A	119.6	C25—C26—H26A	125.1
C5—C6—C1	120.6 (9)	Fe—C26—H26A	125.1
C5—C6—H6A	119.7	C26—C27—C28	108.1 (8)
C1—C6—H6A	119.7	C26—C27—Fe	70.3 (5)
C8—C7—C12	116.4 (7)	C28—C27—Fe	69.9 (5)
C8—C7—P	118.5 (6)	C26—C27—H27A	125.9
C12—C7—P	125.0 (6)	C28—C27—H27A	125.9
C9—C8—C7	122.9 (8)	Fe—C27—H27A	125.9
C9—C8—H8A	118.6	C29—C28—C27	107.7 (9)
C7—C8—H8A	118.6	C29—C28—Fe	69.8 (5)
C10—C9—C8	119.7 (9)	C27—C28—Fe	69.4 (5)
C10—C9—H9A	120.2	C29—C28—H28A	126.2
C8—C9—H9A	120.2	C27—C28—H28A	126.2
C9—C10—C11	120.1 (10)	Fe—C28—H28A	126.2
C9—C10—H10A	120.0	C28—C29—C25	109.2 (9)
C11—C10—H10A	120.0	C28—C29—Fe	70.3 (5)
C10—C11—C12	119.1 (9)	C25—C29—Fe	69.4 (5)
C10—C11—H11A	120.4	C28—C29—H29A	125.4
C12—C11—H11A	120.4	C25—C29—H29A	125.4
C11—C12—C7	121.7 (8)	Fe—C29—H29A	125.4
C7—P—C1—C2	15.4 (9)	C29—Fe—C23—C22	117.6 (5)
C13—P—C1—C2	−90.6 (8)	C25—Fe—C23—C22	160.2 (5)
C7—P—C1—C6	−163.2 (6)	C26—Fe—C23—C22	−171.7 (9)
C13—P—C1—C6	90.8 (7)	C20—Fe—C23—C22	−81.2 (5)
C6—C1—C2—C3	0.5 (15)	C28—Fe—C23—C22	76.9 (5)
P—C1—C2—C3	−178.1 (8)	C22—C23—C24—C20	−3.1 (9)
C1—C2—C3—C4	−2.1 (18)	Fe—C23—C24—C20	−61.1 (5)
C2—C3—C4—C5	2.3 (19)	C22—C23—C24—Fe	58.1 (5)
C3—C4—C5—C6	−0.9 (17)	C21—C20—C24—C23	3.8 (8)
C4—C5—C6—C1	−0.7 (16)	C19—C20—C24—C23	−177.8 (7)
C2—C1—C6—C5	0.9 (13)	Fe—C20—C24—C23	61.2 (5)
P—C1—C6—C5	179.6 (7)	C21—C20—C24—Fe	−57.3 (5)
C13—P—C7—C8	−175.8 (6)	C19—C20—C24—Fe	121.0 (7)
C1—P—C7—C8	78.5 (7)	C21—Fe—C24—C23	−80.2 (5)
C13—P—C7—C12	0.4 (7)	C22—Fe—C24—C23	−37.5 (4)
C1—P—C7—C12	−105.4 (7)	C27—Fe—C24—C23	−166.0 (9)
C12—C7—C8—C9	2.6 (13)	C29—Fe—C24—C23	75.8 (6)
P—C7—C8—C9	179.1 (8)	C25—Fe—C24—C23	118.6 (5)
C7—C8—C9—C10	1.0 (16)	C26—Fe—C24—C23	160.3 (5)
C8—C9—C10—C11	−4.6 (16)	C20—Fe—C24—C23	−117.3 (7)
C9—C10—C11—C12	4.4 (15)	C28—Fe—C24—C23	41.9 (11)
C10—C11—C12—C7	−0.6 (14)	C21—Fe—C24—C20	37.1 (4)
C8—C7—C12—C11	−2.7 (12)	C22—Fe—C24—C20	79.9 (5)
P—C7—C12—C11	−179.0 (7)	C27—Fe—C24—C20	−48.7 (11)
C7—P—C13—C14	77.8 (6)	C29—Fe—C24—C20	−166.9 (5)
C1—P—C13—C14	−177.7 (6)	C25—Fe—C24—C20	−124.1 (5)
C7—P—C13—C18	−107.5 (7)	C26—Fe—C24—C20	−82.4 (6)
C1—P—C13—C18	−3.0 (7)	C28—Fe—C24—C20	159.2 (8)
C18—C13—C14—C15	0.4 (11)	C23—Fe—C24—C20	117.3 (7)
P—C13—C14—C15	175.5 (6)	C21—Fe—C25—C26	46.4 (14)
C18—C13—C14—N	179.8 (6)	C24—Fe—C25—C26	123.0 (6)
P—C13—C14—N	−5.2 (9)	C22—Fe—C25—C26	−160.0 (8)
C19—N—C14—C13	−160.5 (7)	C27—Fe—C25—C26	−35.9 (5)
C19—N—C14—C15	18.8 (12)	C29—Fe—C25—C26	−116.1 (8)
C13—C14—C15—C16	−0.9 (12)	C20—Fe—C25—C26	81.7 (6)
N—C14—C15—C16	179.9 (7)	C28—Fe—C25—C26	−79.8 (6)
C14—C15—C16—C17	0.6 (13)	C23—Fe—C25—C26	165.2 (5)
C15—C16—C17—C18	0.0 (13)	C21—Fe—C25—C29	162.5 (10)
C16—C17—C18—C13	−0.4 (13)	C24—Fe—C25—C29	−120.9 (6)
C14—C13—C18—C17	0.2 (11)	C22—Fe—C25—C29	−43.9 (12)
P—C13—C18—C17	−174.4 (6)	C27—Fe—C25—C29	80.2 (6)
C14—N—C19—C20	−177.9 (6)	C26—Fe—C25—C29	116.1 (9)
N—C19—C20—C24	157.1 (7)	C20—Fe—C25—C29	−162.2 (6)
N—C19—C20—C21	−24.9 (12)	C28—Fe—C25—C29	36.3 (6)
N—C19—C20—Fe	−114.9 (7)	C23—Fe—C25—C29	−78.7 (7)
C21—Fe—C20—C24	−120.7 (7)	C29—C25—C26—C27	−1.9 (10)
C22—Fe—C20—C24	−83.1 (5)	Fe—C25—C26—C27	58.6 (6)
C27—Fe—C20—C24	161.6 (5)	C29—C25—C26—Fe	−60.5 (6)
C29—Fe—C20—C24	36.1 (13)	C21—Fe—C26—C27	74.7 (7)
C25—Fe—C20—C24	75.1 (6)	C24—Fe—C26—C27	162.5 (5)
C26—Fe—C20—C24	119.0 (5)	C22—Fe—C26—C27	36.4 (13)
C28—Fe—C20—C24	−158.9 (9)	C29—Fe—C26—C27	−81.4 (6)
C23—Fe—C20—C24	−38.7 (4)	C25—Fe—C26—C27	−121.3 (8)
C24—Fe—C20—C21	120.7 (7)	C20—Fe—C26—C27	118.7 (6)
C22—Fe—C20—C21	37.6 (4)	C28—Fe—C26—C27	−38.2 (5)
C27—Fe—C20—C21	−77.6 (6)	C23—Fe—C26—C27	−159.2 (9)
C29—Fe—C20—C21	156.8 (11)	C21—Fe—C26—C25	−164.0 (6)
C25—Fe—C20—C21	−164.2 (5)	C24—Fe—C26—C25	−76.2 (7)
C26—Fe—C20—C21	−120.3 (5)	C22—Fe—C26—C25	157.7 (9)
C28—Fe—C20—C21	−38.1 (11)	C27—Fe—C26—C25	121.3 (8)
C23—Fe—C20—C21	82.0 (5)	C29—Fe—C26—C25	39.9 (6)
C21—Fe—C20—C19	121.9 (8)	C20—Fe—C26—C25	−120.0 (6)
C24—Fe—C20—C19	−117.4 (8)	C28—Fe—C26—C25	83.1 (6)
C22—Fe—C20—C19	159.4 (7)	C23—Fe—C26—C25	−37.9 (13)
C27—Fe—C20—C19	44.2 (8)	C25—C26—C27—C28	1.6 (10)
C29—Fe—C20—C19	−81.3 (13)	Fe—C26—C27—C28	59.9 (6)
C25—Fe—C20—C19	−42.3 (8)	C25—C26—C27—Fe	−58.3 (6)
C26—Fe—C20—C19	1.6 (7)	C21—Fe—C27—C26	−124.3 (6)
C28—Fe—C20—C19	83.7 (12)	C24—Fe—C27—C26	−45.7 (12)
C23—Fe—C20—C19	−156.1 (7)	C22—Fe—C27—C26	−165.6 (5)
C24—C20—C21—C22	−3.2 (8)	C29—Fe—C27—C26	81.6 (6)
C19—C20—C21—C22	178.6 (7)	C25—Fe—C27—C26	36.8 (6)
Fe—C20—C21—C22	−60.8 (5)	C20—Fe—C27—C26	−82.0 (6)
C24—C20—C21—Fe	57.7 (5)	C28—Fe—C27—C26	118.9 (8)
C19—C20—C21—Fe	−120.6 (7)	C23—Fe—C27—C26	159.9 (8)
C24—Fe—C21—C22	81.5 (5)	C21—Fe—C27—C28	116.8 (5)
C27—Fe—C21—C22	−119.8 (5)	C24—Fe—C27—C28	−164.6 (8)
C29—Fe—C21—C22	−44.1 (10)	C22—Fe—C27—C28	75.5 (6)
C25—Fe—C21—C22	164.4 (10)	C29—Fe—C27—C28	−37.3 (5)
C26—Fe—C21—C22	−160.1 (5)	C25—Fe—C27—C28	−82.1 (5)
C20—Fe—C21—C22	118.3 (6)	C26—Fe—C27—C28	−118.9 (8)
C28—Fe—C21—C22	−77.0 (6)	C20—Fe—C27—C28	159.1 (5)
C23—Fe—C21—C22	37.8 (4)	C23—Fe—C27—C28	41.0 (11)
C24—Fe—C21—C20	−36.8 (4)	C26—C27—C28—C29	−0.6 (10)
C22—Fe—C21—C20	−118.3 (6)	Fe—C27—C28—C29	59.5 (6)
C27—Fe—C21—C20	121.9 (5)	C26—C27—C28—Fe	−60.1 (6)
C29—Fe—C21—C20	−162.4 (8)	C21—Fe—C28—C29	159.3 (6)
C25—Fe—C21—C20	46.1 (13)	C24—Fe—C28—C29	46.7 (12)
C26—Fe—C21—C20	81.6 (5)	C22—Fe—C28—C29	118.9 (6)
C28—Fe—C21—C20	164.7 (5)	C27—Fe—C28—C29	−119.0 (8)
C23—Fe—C21—C20	−80.5 (5)	C25—Fe—C28—C29	−37.7 (6)
C20—C21—C22—C23	1.2 (8)	C26—Fe—C28—C29	−81.8 (6)
Fe—C21—C22—C23	−59.6 (5)	C20—Fe—C28—C29	−172.6 (8)
C20—C21—C22—Fe	60.8 (5)	C23—Fe—C28—C29	77.4 (7)
C24—Fe—C22—C21	−82.5 (5)	C21—Fe—C28—C27	−81.8 (6)
C27—Fe—C22—C21	78.7 (6)	C24—Fe—C28—C27	165.6 (8)
C29—Fe—C22—C21	160.3 (5)	C22—Fe—C28—C27	−122.2 (5)
C25—Fe—C22—C21	−167.6 (8)	C29—Fe—C28—C27	119.0 (8)
C26—Fe—C22—C21	52.0 (11)	C25—Fe—C28—C27	81.3 (6)
C20—Fe—C22—C21	−38.6 (4)	C26—Fe—C28—C27	37.2 (5)
C28—Fe—C22—C21	119.7 (5)	C20—Fe—C28—C27	−53.6 (11)
C23—Fe—C22—C21	−119.7 (7)	C23—Fe—C28—C27	−163.7 (5)
C21—Fe—C22—C23	119.7 (7)	C27—C28—C29—C25	−0.6 (10)
C24—Fe—C22—C23	37.2 (4)	Fe—C28—C29—C25	58.6 (6)
C27—Fe—C22—C23	−161.6 (5)	C27—C28—C29—Fe	−59.3 (6)
C29—Fe—C22—C23	−80.0 (6)	C26—C25—C29—C28	1.5 (10)
C25—Fe—C22—C23	−47.9 (10)	Fe—C25—C29—C28	−59.2 (6)
C26—Fe—C22—C23	171.6 (9)	C26—C25—C29—Fe	60.7 (6)
C20—Fe—C22—C23	81.1 (5)	C21—Fe—C29—C28	−46.6 (11)
C28—Fe—C22—C23	−120.6 (5)	C24—Fe—C29—C28	−161.1 (6)
C21—C22—C23—C24	1.2 (9)	C22—Fe—C29—C28	−77.7 (7)
Fe—C22—C23—C24	−58.1 (5)	C27—Fe—C29—C28	38.1 (6)
C21—C22—C23—Fe	59.3 (5)	C25—Fe—C29—C28	120.5 (9)
C21—Fe—C23—C24	83.2 (5)	C26—Fe—C29—C28	81.1 (6)
C22—Fe—C23—C24	120.0 (7)	C20—Fe—C29—C28	171.5 (9)
C27—Fe—C23—C24	166.7 (8)	C23—Fe—C29—C28	−120.0 (6)
C29—Fe—C23—C24	−122.4 (5)	C21—Fe—C29—C25	−167.1 (7)
C25—Fe—C23—C24	−79.8 (6)	C24—Fe—C29—C25	78.4 (7)
C26—Fe—C23—C24	−51.7 (12)	C22—Fe—C29—C25	161.8 (5)
C20—Fe—C23—C24	38.8 (4)	C27—Fe—C29—C25	−82.3 (6)
C28—Fe—C23—C24	−163.1 (5)	C26—Fe—C29—C25	−39.3 (5)
C21—Fe—C23—C22	−36.8 (4)	C20—Fe—C29—C25	51.0 (14)
C24—Fe—C23—C22	−120.0 (7)	C28—Fe—C29—C25	−120.5 (9)
C27—Fe—C23—C22	46.7 (11)	C23—Fe—C29—C25	119.5 (6)