N-Methyl-N-(ferrocenylmeth­yl)aniline

The title compound, [Fe(C₅H₅)(C₁₃H₁₄N)], a tertiary aryl­amine bearing a ferrocenyl group was synthesized by reductive methyl­ation of amines. The result reveals that the cyclo­penta­diene ring carrying the methyl­aniline residue is nearly perpendicular to the benzene plane [dihedral angle = 92.1 (3)°].

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.039
• wR factor = 0.100
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        Fe1

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8

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

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

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

N-methyl-N-(ferrocenylmethyl)aniline

Crystal data

[Fe(C5H5)(C13H14N)]	Dx = 1.327 Mg m^−3
Mr = 305.19	Melting point: 327 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.626 (2) Å	Cell parameters from 2691 reflections
b = 11.675 (2) Å	θ = 2.2–24.4°
c = 14.062 (3) Å	µ = 0.98 mm^−1
β = 104.762 (4)°	T = 294 K
V = 1528.1 (5) Å^3	Block, yellow
Z = 4	0.34 × 0.30 × 0.22 mm
F(000) = 640

Data collection

Bruker SMART CCD area-detector diffractometer	3089 independent reflections
Radiation source: fine-focus sealed tube	2166 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 26.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.704, Tmax = 0.807	k = −14→13
8371 measured reflections	l = −10→17

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.043P)^2 + 0.4801P] where P = (Fo^2 + 2Fc^2)/3
3089 reflections	(Δ/σ)max = 0.003
182 parameters	Δρmax = 0.49 e Å^−3
18 restraints	Δρmin = −0.38 e Å^−3

Special details

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
Fe1	0.61561 (4)	0.65384 (3)	0.15894 (3)	0.04477 (15)
N1	0.9675 (3)	0.4031 (3)	0.1781 (2)	0.0764 (8)
C1	0.5626 (4)	0.6000 (4)	0.2815 (2)	0.0786 (10)
H1	0.6131	0.5463	0.3260	0.094*
C2	0.4504 (3)	0.5777 (3)	0.1997 (2)	0.0674 (9)
H2	0.4132	0.5056	0.1798	0.081*
C3	0.4029 (4)	0.6785 (3)	0.1529 (3)	0.0783 (10)
H3	0.3279	0.6866	0.0966	0.094*
C4	0.4853 (6)	0.7652 (3)	0.2035 (4)	0.1005 (14)
H4	0.4759	0.8424	0.1868	0.121*
C5	0.5859 (5)	0.7191 (5)	0.2845 (3)	0.1002 (15)
H5	0.6546	0.7593	0.3310	0.120*
C6	0.6812 (3)	0.5473 (3)	0.06382 (19)	0.0573 (7)
H6	0.6419	0.4765	0.0413	0.069*
C7	0.6376 (4)	0.6534 (3)	0.0188 (2)	0.0681 (9)
H7	0.5646	0.6649	−0.0381	0.082*
C8	0.7235 (4)	0.7389 (3)	0.0747 (3)	0.0774 (10)
H8	0.7168	0.8171	0.0617	0.093*
C9	0.8222 (3)	0.6853 (3)	0.1545 (2)	0.0687 (9)
H9	0.8928	0.7222	0.2022	0.082*
C10	0.7948 (3)	0.5656 (3)	0.14897 (19)	0.0544 (7)
C11	0.8731 (4)	0.4746 (3)	0.2194 (2)	0.0785 (10)
H11A	0.9298	0.5117	0.2783	0.094*
H11B	0.8030	0.4261	0.2385	0.094*
C12	1.0883 (4)	0.4648 (4)	0.1588 (3)	0.1031 (14)
H12A	1.1659	0.4124	0.1608	0.155*
H12B	1.1192	0.5230	0.2078	0.155*
H12C	1.0596	0.4997	0.0949	0.155*
C13	0.9138 (3)	0.3071 (3)	0.1226 (2)	0.0599 (8)
C14	0.9802 (3)	0.2644 (3)	0.0520 (2)	0.0701 (9)
H14	1.0556	0.3049	0.0378	0.084*
C15	0.9354 (4)	0.1637 (4)	0.0037 (3)	0.0872 (11)
H15	0.9831	0.1363	−0.0415	0.105*
C16	0.8228 (5)	0.1023 (4)	0.0200 (3)	0.0920 (12)
H16	0.7935	0.0342	−0.0135	0.110*
C17	0.7542 (4)	0.1439 (4)	0.0870 (3)	0.0914 (12)
H17	0.6767	0.1037	0.0985	0.110*
C18	0.7975 (4)	0.2441 (3)	0.1378 (3)	0.0779 (10)
H18	0.7487	0.2703	0.1828	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0483 (2)	0.0461 (2)	0.0426 (2)	−0.00257 (19)	0.01652 (16)	−0.00469 (17)
N1	0.0459 (15)	0.081 (2)	0.099 (2)	0.0144 (14)	0.0129 (14)	−0.0068 (17)
C1	0.075 (2)	0.114 (3)	0.055 (2)	0.009 (2)	0.0302 (18)	0.021 (2)
C2	0.062 (2)	0.069 (2)	0.078 (2)	−0.0128 (17)	0.0312 (18)	−0.0071 (18)
C3	0.060 (2)	0.101 (3)	0.080 (2)	0.026 (2)	0.0293 (18)	0.008 (2)
C4	0.136 (4)	0.062 (2)	0.132 (4)	0.015 (2)	0.087 (3)	−0.014 (2)
C5	0.103 (3)	0.140 (4)	0.075 (3)	−0.056 (3)	0.052 (2)	−0.068 (3)
C6	0.0563 (17)	0.073 (2)	0.0434 (15)	0.0061 (15)	0.0143 (13)	−0.0121 (14)
C7	0.071 (2)	0.094 (3)	0.0441 (16)	0.005 (2)	0.0227 (14)	0.0070 (17)
C8	0.083 (2)	0.074 (2)	0.090 (3)	−0.005 (2)	0.047 (2)	0.020 (2)
C9	0.0538 (19)	0.084 (2)	0.072 (2)	−0.0210 (17)	0.0242 (16)	−0.0167 (18)
C10	0.0424 (15)	0.075 (2)	0.0465 (15)	0.0039 (14)	0.0120 (12)	−0.0128 (14)
C11	0.069 (2)	0.099 (3)	0.061 (2)	0.025 (2)	0.0044 (16)	−0.0071 (18)
C12	0.057 (2)	0.094 (3)	0.153 (4)	0.002 (2)	0.018 (2)	−0.021 (3)
C13	0.0419 (16)	0.071 (2)	0.0657 (19)	0.0170 (15)	0.0120 (14)	0.0138 (16)
C14	0.0543 (19)	0.080 (2)	0.081 (2)	0.0100 (17)	0.0256 (17)	0.0102 (19)
C15	0.081 (3)	0.089 (3)	0.093 (3)	0.021 (2)	0.026 (2)	0.000 (2)
C16	0.093 (3)	0.074 (3)	0.096 (3)	0.006 (2)	0.001 (2)	0.001 (2)
C17	0.074 (3)	0.089 (3)	0.107 (3)	−0.013 (2)	0.016 (2)	0.025 (3)
C18	0.063 (2)	0.098 (3)	0.078 (2)	0.009 (2)	0.0279 (18)	0.013 (2)

Geometric parameters (Å, º)

Fe1—C5	2.009 (3)	C6—H6	0.9300
Fe1—C4	2.015 (3)	C7—C8	1.402 (5)
Fe1—C1	2.018 (3)	C7—H7	0.9300
Fe1—C8	2.023 (3)	C8—C9	1.418 (5)
Fe1—C2	2.028 (3)	C8—H8	0.9300
Fe1—C7	2.035 (3)	C9—C10	1.421 (4)
Fe1—C9	2.039 (3)	C9—H9	0.9300
Fe1—C6	2.041 (3)	C10—C11	1.516 (4)
Fe1—C10	2.044 (3)	C11—H11A	0.9700
Fe1—C3	2.048 (3)	C11—H11B	0.9700
N1—C13	1.388 (4)	C12—H12A	0.9600
N1—C12	1.451 (4)	C12—H12B	0.9600
N1—C11	1.459 (4)	C12—H12C	0.9600
C1—C2	1.387 (5)	C13—C18	1.401 (4)
C1—C5	1.408 (6)	C13—C14	1.401 (4)
C1—H1	0.9300	C14—C15	1.371 (5)
C2—C3	1.368 (5)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.367 (5)
C3—C4	1.369 (5)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.370 (5)
C4—C5	1.401 (6)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.378 (5)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.406 (4)	C18—H18	0.9300
C6—C10	1.417 (4)
C5—Fe1—C4	40.76 (17)	C3—C4—H4	125.4
C5—Fe1—C1	40.92 (17)	C5—C4—H4	125.4
C4—Fe1—C1	67.83 (17)	Fe1—C4—H4	125.1
C5—Fe1—C8	122.52 (18)	C4—C5—C1	106.5 (3)
C4—Fe1—C8	108.58 (16)	C4—C5—Fe1	69.83 (19)
C1—Fe1—C8	158.72 (17)	C1—C5—Fe1	69.89 (18)
C5—Fe1—C2	67.69 (14)	C4—C5—H5	126.8
C4—Fe1—C2	66.39 (16)	C1—C5—H5	126.8
C1—Fe1—C2	40.10 (14)	Fe1—C5—H5	125.1
C8—Fe1—C2	159.55 (15)	C7—C6—C10	109.0 (3)
C5—Fe1—C7	157.7 (2)	C7—C6—Fe1	69.59 (16)
C4—Fe1—C7	121.98 (18)	C10—C6—Fe1	69.83 (15)
C1—Fe1—C7	159.62 (17)	C7—C6—H6	125.5
C8—Fe1—C7	40.42 (13)	C10—C6—H6	125.5
C2—Fe1—C7	123.73 (14)	Fe1—C6—H6	126.7
C5—Fe1—C9	108.48 (14)	C8—C7—C6	108.0 (3)
C4—Fe1—C9	125.65 (17)	C8—C7—Fe1	69.35 (17)
C1—Fe1—C9	122.89 (15)	C6—C7—Fe1	70.06 (16)
C8—Fe1—C9	40.85 (13)	C8—C7—H7	126.0
C2—Fe1—C9	158.27 (15)	C6—C7—H7	126.0
C7—Fe1—C9	68.15 (14)	Fe1—C7—H7	126.2
C5—Fe1—C6	160.8 (2)	C7—C8—C9	108.1 (3)
C4—Fe1—C6	156.70 (19)	C7—C8—Fe1	70.23 (17)
C1—Fe1—C6	123.88 (15)	C9—C8—Fe1	70.16 (18)
C8—Fe1—C6	67.95 (14)	C7—C8—H8	126.0
C2—Fe1—C6	108.31 (13)	C9—C8—H8	126.0
C7—Fe1—C6	40.35 (12)	Fe1—C8—H8	125.2
C9—Fe1—C6	67.83 (12)	C8—C9—C10	108.2 (3)
C5—Fe1—C10	124.25 (18)	C8—C9—Fe1	68.99 (18)
C4—Fe1—C10	161.78 (19)	C10—C9—Fe1	69.83 (16)
C1—Fe1—C10	107.61 (14)	C8—C9—H9	125.9
C8—Fe1—C10	68.87 (14)	C10—C9—H9	125.9
C2—Fe1—C10	122.31 (14)	Fe1—C9—H9	126.9
C7—Fe1—C10	68.57 (12)	C6—C10—C9	106.7 (3)
C9—Fe1—C10	40.74 (12)	C6—C10—C11	126.5 (3)
C6—Fe1—C10	40.58 (11)	C9—C10—C11	126.8 (3)
C5—Fe1—C3	67.58 (16)	C6—C10—Fe1	69.59 (16)
C4—Fe1—C3	39.37 (16)	C9—C10—Fe1	69.43 (17)
C1—Fe1—C3	67.16 (14)	C11—C10—Fe1	126.6 (2)
C8—Fe1—C3	124.30 (16)	N1—C11—C10	113.4 (3)
C2—Fe1—C3	39.23 (13)	N1—C11—H11A	108.9
C7—Fe1—C3	108.04 (14)	C10—C11—H11A	108.9
C9—Fe1—C3	161.11 (15)	N1—C11—H11B	108.9
C6—Fe1—C3	122.10 (14)	C10—C11—H11B	108.9
C10—Fe1—C3	156.92 (14)	H11A—C11—H11B	107.7
C13—N1—C12	119.7 (3)	N1—C12—H12A	109.5
C13—N1—C11	120.4 (3)	N1—C12—H12B	109.5
C12—N1—C11	113.6 (3)	H12A—C12—H12B	109.5
C2—C1—C5	107.1 (4)	N1—C12—H12C	109.5
C2—C1—Fe1	70.33 (18)	H12A—C12—H12C	109.5
C5—C1—Fe1	69.20 (19)	H12B—C12—H12C	109.5
C2—C1—H1	126.4	N1—C13—C18	122.3 (3)
C5—C1—H1	126.4	N1—C13—C14	121.0 (3)
Fe1—C1—H1	125.6	C18—C13—C14	116.6 (3)
C3—C2—C1	109.4 (3)	C15—C14—C13	120.9 (3)
C3—C2—Fe1	71.17 (19)	C15—C14—H14	119.5
C1—C2—Fe1	69.58 (18)	C13—C14—H14	119.5
C3—C2—H2	125.3	C16—C15—C14	121.9 (4)
C1—C2—H2	125.3	C16—C15—H15	119.0
Fe1—C2—H2	125.5	C14—C15—H15	119.0
C4—C3—C2	107.9 (4)	C15—C16—C17	118.1 (4)
C4—C3—Fe1	69.0 (2)	C15—C16—H16	121.0
C2—C3—Fe1	69.60 (18)	C17—C16—H16	121.0
C4—C3—H3	126.0	C16—C17—C18	121.5 (4)
C2—C3—H3	126.0	C16—C17—H17	119.2
Fe1—C3—H3	126.9	C18—C17—H17	119.2
C3—C4—C5	109.1 (4)	C17—C18—C13	120.9 (3)
C3—C4—Fe1	71.6 (2)	C17—C18—H18	119.5
C5—C4—Fe1	69.4 (2)	C13—C18—H18	119.5
C5—Fe1—C1—C2	118.0 (3)	C3—Fe1—C6—C10	−159.55 (19)
C4—Fe1—C1—C2	79.2 (3)	C10—C6—C7—C8	0.3 (3)
C8—Fe1—C1—C2	163.6 (4)	Fe1—C6—C7—C8	59.2 (2)
C7—Fe1—C1—C2	−43.9 (5)	C10—C6—C7—Fe1	−58.86 (19)
C9—Fe1—C1—C2	−161.7 (2)	C5—Fe1—C7—C8	47.3 (5)
C6—Fe1—C1—C2	−77.9 (2)	C4—Fe1—C7—C8	81.2 (3)
C10—Fe1—C1—C2	−119.6 (2)	C1—Fe1—C7—C8	−165.1 (4)
C3—Fe1—C1—C2	36.4 (2)	C2—Fe1—C7—C8	162.5 (2)
C4—Fe1—C1—C5	−38.9 (3)	C9—Fe1—C7—C8	−38.2 (2)
C8—Fe1—C1—C5	45.5 (5)	C6—Fe1—C7—C8	−119.2 (3)
C2—Fe1—C1—C5	−118.0 (3)	C10—Fe1—C7—C8	−82.2 (2)
C7—Fe1—C1—C5	−161.9 (4)	C3—Fe1—C7—C8	122.1 (2)
C9—Fe1—C1—C5	80.2 (3)	C5—Fe1—C7—C6	166.6 (4)
C6—Fe1—C1—C5	164.1 (3)	C4—Fe1—C7—C6	−159.6 (2)
C10—Fe1—C1—C5	122.4 (3)	C1—Fe1—C7—C6	−45.9 (5)
C3—Fe1—C1—C5	−81.6 (3)	C8—Fe1—C7—C6	119.2 (3)
C5—C1—C2—C3	−0.6 (4)	C2—Fe1—C7—C6	−78.3 (2)
Fe1—C1—C2—C3	−60.2 (2)	C9—Fe1—C7—C6	81.0 (2)
C5—C1—C2—Fe1	59.7 (2)	C10—Fe1—C7—C6	37.05 (18)
C5—Fe1—C2—C3	81.4 (3)	C3—Fe1—C7—C6	−118.7 (2)
C4—Fe1—C2—C3	37.0 (2)	C6—C7—C8—C9	0.6 (4)
C1—Fe1—C2—C3	120.1 (3)	Fe1—C7—C8—C9	60.2 (2)
C8—Fe1—C2—C3	−42.8 (5)	C6—C7—C8—Fe1	−59.6 (2)
C7—Fe1—C2—C3	−76.8 (3)	C5—Fe1—C8—C7	−160.7 (3)
C9—Fe1—C2—C3	165.4 (3)	C4—Fe1—C8—C7	−117.8 (3)
C6—Fe1—C2—C3	−118.7 (2)	C1—Fe1—C8—C7	165.7 (4)
C10—Fe1—C2—C3	−161.2 (2)	C2—Fe1—C8—C7	−45.8 (5)
C5—Fe1—C2—C1	−38.7 (3)	C9—Fe1—C8—C7	118.7 (3)
C4—Fe1—C2—C1	−83.1 (3)	C6—Fe1—C8—C7	37.57 (19)
C8—Fe1—C2—C1	−162.9 (4)	C10—Fe1—C8—C7	81.4 (2)
C7—Fe1—C2—C1	163.1 (2)	C3—Fe1—C8—C7	−77.1 (3)
C9—Fe1—C2—C1	45.3 (4)	C5—Fe1—C8—C9	80.6 (3)
C6—Fe1—C2—C1	121.2 (2)	C4—Fe1—C8—C9	123.5 (3)
C10—Fe1—C2—C1	78.7 (3)	C1—Fe1—C8—C9	47.0 (5)
C3—Fe1—C2—C1	−120.1 (3)	C2—Fe1—C8—C9	−164.5 (3)
C1—C2—C3—C4	0.7 (4)	C7—Fe1—C8—C9	−118.7 (3)
Fe1—C2—C3—C4	−58.5 (2)	C6—Fe1—C8—C9	−81.1 (2)
C1—C2—C3—Fe1	59.3 (2)	C10—Fe1—C8—C9	−37.35 (19)
C5—Fe1—C3—C4	37.9 (3)	C3—Fe1—C8—C9	164.2 (2)
C1—Fe1—C3—C4	82.4 (3)	C7—C8—C9—C10	−1.3 (4)
C8—Fe1—C3—C4	−77.1 (3)	Fe1—C8—C9—C10	59.0 (2)
C2—Fe1—C3—C4	119.6 (3)	C7—C8—C9—Fe1	−60.3 (2)
C7—Fe1—C3—C4	−118.8 (3)	C5—Fe1—C9—C8	−118.7 (3)
C9—Fe1—C3—C4	−43.7 (5)	C4—Fe1—C9—C8	−76.7 (3)
C6—Fe1—C3—C4	−160.9 (3)	C1—Fe1—C9—C8	−161.6 (2)
C10—Fe1—C3—C4	163.7 (3)	C2—Fe1—C9—C8	165.4 (3)
C5—Fe1—C3—C2	−81.7 (3)	C7—Fe1—C9—C8	37.8 (2)
C4—Fe1—C3—C2	−119.6 (3)	C6—Fe1—C9—C8	81.5 (2)
C1—Fe1—C3—C2	−37.2 (2)	C10—Fe1—C9—C8	119.9 (3)
C8—Fe1—C3—C2	163.3 (2)	C3—Fe1—C9—C8	−44.1 (5)
C7—Fe1—C3—C2	121.6 (2)	C5—Fe1—C9—C10	121.4 (2)
C9—Fe1—C3—C2	−163.3 (4)	C4—Fe1—C9—C10	163.4 (2)
C6—Fe1—C3—C2	79.5 (2)	C1—Fe1—C9—C10	78.5 (2)
C10—Fe1—C3—C2	44.1 (4)	C8—Fe1—C9—C10	−119.9 (3)
C2—C3—C4—C5	−0.6 (4)	C2—Fe1—C9—C10	45.5 (4)
Fe1—C3—C4—C5	−59.5 (3)	C7—Fe1—C9—C10	−82.09 (19)
C2—C3—C4—Fe1	58.9 (2)	C6—Fe1—C9—C10	−38.41 (17)
C5—Fe1—C4—C3	−119.6 (4)	C3—Fe1—C9—C10	−164.0 (4)
C1—Fe1—C4—C3	−80.5 (3)	C7—C6—C10—C9	−1.1 (3)
C8—Fe1—C4—C3	121.8 (3)	Fe1—C6—C10—C9	−59.82 (19)
C2—Fe1—C4—C3	−36.9 (2)	C7—C6—C10—C11	179.8 (3)
C7—Fe1—C4—C3	79.3 (3)	Fe1—C6—C10—C11	121.1 (3)
C9—Fe1—C4—C3	164.0 (2)	C7—C6—C10—Fe1	58.7 (2)
C6—Fe1—C4—C3	44.6 (5)	C8—C9—C10—C6	1.5 (3)
C10—Fe1—C4—C3	−159.4 (4)	Fe1—C9—C10—C6	59.92 (18)
C1—Fe1—C4—C5	39.0 (2)	C8—C9—C10—C11	−179.5 (3)
C8—Fe1—C4—C5	−118.6 (3)	Fe1—C9—C10—C11	−121.0 (3)
C2—Fe1—C4—C5	82.7 (3)	C8—C9—C10—Fe1	−58.5 (2)
C7—Fe1—C4—C5	−161.1 (2)	C5—Fe1—C10—C6	163.9 (2)
C9—Fe1—C4—C5	−76.4 (3)	C4—Fe1—C10—C6	−165.7 (5)
C6—Fe1—C4—C5	164.1 (3)	C1—Fe1—C10—C6	121.9 (2)
C10—Fe1—C4—C5	−39.8 (6)	C8—Fe1—C10—C6	−80.4 (2)
C3—Fe1—C4—C5	119.6 (4)	C2—Fe1—C10—C6	80.4 (2)
C3—C4—C5—C1	0.3 (4)	C7—Fe1—C10—C6	−36.84 (18)
Fe1—C4—C5—C1	−60.6 (2)	C9—Fe1—C10—C6	−117.8 (3)
C3—C4—C5—Fe1	60.9 (3)	C3—Fe1—C10—C6	49.0 (4)
C2—C1—C5—C4	0.2 (4)	C5—Fe1—C10—C9	−78.3 (3)
Fe1—C1—C5—C4	60.6 (2)	C4—Fe1—C10—C9	−47.9 (5)
C2—C1—C5—Fe1	−60.4 (2)	C1—Fe1—C10—C9	−120.3 (2)
C1—Fe1—C5—C4	−117.1 (3)	C8—Fe1—C10—C9	37.4 (2)
C8—Fe1—C5—C4	80.7 (3)	C2—Fe1—C10—C9	−161.8 (2)
C2—Fe1—C5—C4	−79.2 (3)	C7—Fe1—C10—C9	81.0 (2)
C7—Fe1—C5—C4	46.3 (5)	C6—Fe1—C10—C9	117.8 (3)
C9—Fe1—C5—C4	123.6 (3)	C3—Fe1—C10—C9	166.8 (3)
C6—Fe1—C5—C4	−160.9 (4)	C5—Fe1—C10—C11	42.9 (4)
C10—Fe1—C5—C4	166.0 (2)	C4—Fe1—C10—C11	73.3 (6)
C3—Fe1—C5—C4	−36.6 (2)	C1—Fe1—C10—C11	0.9 (3)
C4—Fe1—C5—C1	117.1 (3)	C8—Fe1—C10—C11	158.6 (3)
C8—Fe1—C5—C1	−162.1 (2)	C2—Fe1—C10—C11	−40.6 (3)
C2—Fe1—C5—C1	37.9 (2)	C7—Fe1—C10—C11	−157.8 (3)
C7—Fe1—C5—C1	163.4 (3)	C9—Fe1—C10—C11	121.2 (3)
C9—Fe1—C5—C1	−119.2 (2)	C6—Fe1—C10—C11	−121.0 (4)
C6—Fe1—C5—C1	−43.7 (5)	C3—Fe1—C10—C11	−72.0 (4)
C10—Fe1—C5—C1	−76.9 (3)	C13—N1—C11—C10	−86.0 (4)
C3—Fe1—C5—C1	80.5 (2)	C12—N1—C11—C10	66.1 (4)
C5—Fe1—C6—C7	−164.5 (4)	C6—C10—C11—N1	71.4 (4)
C4—Fe1—C6—C7	48.3 (4)	C9—C10—C11—N1	−107.5 (3)
C1—Fe1—C6—C7	162.5 (2)	Fe1—C10—C11—N1	162.0 (2)
C8—Fe1—C6—C7	−37.6 (2)	C12—N1—C13—C18	−180.0 (3)
C2—Fe1—C6—C7	120.9 (2)	C11—N1—C13—C18	−29.5 (5)
C9—Fe1—C6—C7	−81.9 (2)	C12—N1—C13—C14	4.0 (5)
C10—Fe1—C6—C7	−120.4 (3)	C11—N1—C13—C14	154.5 (3)
C3—Fe1—C6—C7	80.0 (2)	N1—C13—C14—C15	173.9 (3)
C5—Fe1—C6—C10	−44.0 (5)	C18—C13—C14—C15	−2.3 (5)
C4—Fe1—C6—C10	168.7 (3)	C13—C14—C15—C16	1.7 (6)
C1—Fe1—C6—C10	−77.1 (2)	C14—C15—C16—C17	−0.1 (6)
C8—Fe1—C6—C10	82.8 (2)	C15—C16—C17—C18	−0.7 (6)
C2—Fe1—C6—C10	−118.6 (2)	C16—C17—C18—C13	−0.1 (6)
C7—Fe1—C6—C10	120.4 (3)	N1—C13—C18—C17	−174.6 (3)
C9—Fe1—C6—C10	38.56 (19)	C14—C13—C18—C17	1.5 (5)