1-Ferrocenyl-3-(3-fluoro-anilino)propan-1-one.

The title ferrocene derivative, [Fe(C(5)H(5))(C(14)H(13)FNO)], crystallizes in the same space group with similar unit-cell parameters as the derivatives 3-anilino-1-ferrocenylpropan-1-one [Leka et al. (2012 ▶). Acta Cryst. E68, m229] and 1-ferrocenyl-3-(4-methyl-anilino)propan-1-one [Leka et al. (2012 ▶). Acta Cryst. E68, m230]. The dihedral angle between the best planes of the benzene ring and the substituted cyclo-penta-dienyl ring is 83.4 (1)°. The presence of the electronegative fluoro substituent in the meta position of the aniline group does not alter the crystal packing compared to the other two derivatives. The molecules are connected into centrosymmetric dimers via N-H⋯O hydrogen bonds. In addition, C-H⋯O and C-H⋯N contacts stabilize the crystal packing.

Related literature

For the physico-chemical properties of ferrocene-based compounds see: Togni & Hayashi (1995 ▶). For related crystal structures and details of the synthesis see: Damljanović et al. (2011 ▶); Stevanović et al. (2012 ▶); Leka et al. (2012a ▶,b ▶).

Experimental

Crystal data

[Fe(C5H5)(C14H13FNO)]

M = 351.19

Triclinic,

a = 7.6602 (4) Å

b = 9.6438 (4) Å

c = 12.0626 (6) Å

α = 86.548 (4)°

β = 73.590 (4)°

γ = 69.138 (4)°

V = 797.95 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.96 mm−1

T = 293 K

0.30 × 0.24 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.892, T max = 1.000

6470 measured reflections

3637 independent reflections

2733 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.102

S = 1.06

3637 reflections

212 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.42 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and POV-RAY (Persistence of Vision, 2004 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PLATON (Spek, 2009 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812003510/bt5792sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003510/bt5792Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Fe(C5H5)(C14H13FNO)]	Z = 2
Mr = 351.19	F(000) = 364
Triclinic, P1	Dx = 1.462 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6602 (4) Å	Cell parameters from 2586 reflections
b = 9.6438 (4) Å	θ = 3.0–29.0°
c = 12.0626 (6) Å	µ = 0.96 mm−1
α = 86.548 (4)°	T = 293 K
β = 73.590 (4)°	Prismatic, orange
γ = 69.138 (4)°	0.30 × 0.24 × 0.22 mm
V = 797.95 (7) Å3

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer	3637 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2733 reflections with I > 2σ(I)
graphite	Rint = 0.039
Detector resolution: 16.3280 pixels mm-1	θmax = 29.0°, θmin = 3.0°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→13
Tmin = 0.892, Tmax = 1.000	l = −16→16
6470 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0311P)2 + 0.0409P] where P = (Fo2 + 2Fc2)/3
3637 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

	x	y	z	Uiso*/Ueq
Fe	−0.00273 (5)	0.82243 (4)	0.71263 (3)	0.04303 (14)
F1	0.7892 (3)	0.3862 (3)	0.90812 (18)	0.0882 (7)
O1	0.2719 (2)	0.5199 (2)	0.48403 (16)	0.0499 (5)
N1	0.4911 (3)	0.2934 (3)	0.6422 (2)	0.0449 (6)
C1	−0.0198 (3)	0.6710 (3)	0.6119 (2)	0.0372 (6)
C2	−0.1753 (3)	0.7020 (3)	0.7169 (2)	0.0448 (7)
H2	−0.1983	0.6335	0.7714	0.054*
C3	−0.2873 (4)	0.8550 (3)	0.7229 (3)	0.0536 (8)
H3	−0.3970	0.9051	0.7823	0.064*
C4	−0.2040 (4)	0.9184 (3)	0.6233 (3)	0.0560 (8)
H4	−0.2504	1.0178	0.6057	0.067*
C5	−0.0400 (4)	0.8082 (3)	0.5550 (2)	0.0473 (7)
H5	0.0413	0.8216	0.4850	0.057*
C6	0.2666 (5)	0.7445 (4)	0.7374 (4)	0.0795 (12)
H6	0.3657	0.6561	0.7055	0.095*
C7	0.1231 (8)	0.7621 (6)	0.8431 (4)	0.0967 (15)
H7	0.1092	0.6879	0.8941	0.116*
C8	0.0042 (6)	0.9130 (6)	0.8577 (4)	0.0878 (12)
H8	−0.1030	0.9561	0.9206	0.105*
C9	0.0721 (5)	0.9861 (4)	0.7643 (4)	0.0719 (10)
H9	0.0192	1.0871	0.7533	0.086*
C10	0.2342 (4)	0.8836 (4)	0.6881 (3)	0.0671 (9)
H10	0.3074	0.9040	0.6176	0.081*
C11	0.1432 (3)	0.5307 (3)	0.5732 (2)	0.0363 (6)
C12	0.1427 (3)	0.3981 (3)	0.6467 (2)	0.0404 (6)
H12A	0.0391	0.3664	0.6403	0.048*
H12B	0.1158	0.4275	0.7270	0.048*
C13	0.3347 (3)	0.2684 (3)	0.6115 (2)	0.0443 (7)
H13A	0.3168	0.1803	0.6483	0.053*
H13B	0.3718	0.2496	0.5285	0.053*
C14	0.5010 (3)	0.2932 (3)	0.7547 (2)	0.0397 (6)
C15	0.3909 (4)	0.2347 (3)	0.8445 (3)	0.0551 (8)
H15	0.2988	0.2008	0.8311	0.066*
C16	0.4193 (4)	0.2273 (4)	0.9534 (3)	0.0674 (10)
H16	0.3464	0.1870	1.0123	0.081*
C17	0.5519 (4)	0.2778 (4)	0.9769 (3)	0.0672 (9)
H17	0.5706	0.2723	1.0502	0.081*
C18	0.6549 (4)	0.3361 (4)	0.8883 (3)	0.0553 (8)
C19	0.6334 (3)	0.3462 (3)	0.7795 (2)	0.0458 (7)
H19	0.7066	0.3882	0.7222	0.055*
H1N	0.541 (4)	0.349 (3)	0.601 (2)	0.044 (8)*

	U11	U22	U33	U12	U13	U23
Fe	0.0435 (2)	0.0423 (2)	0.0477 (3)	−0.01725 (18)	−0.01646 (18)	0.00022 (17)
F1	0.0864 (13)	0.1340 (19)	0.0769 (15)	−0.0679 (14)	−0.0380 (11)	0.0171 (13)
O1	0.0517 (11)	0.0520 (11)	0.0418 (12)	−0.0225 (9)	−0.0014 (9)	0.0042 (9)
N1	0.0368 (12)	0.0494 (14)	0.0487 (16)	−0.0169 (11)	−0.0119 (11)	0.0105 (12)
C1	0.0404 (13)	0.0377 (13)	0.0416 (16)	−0.0184 (11)	−0.0182 (12)	0.0036 (11)
C2	0.0397 (13)	0.0473 (16)	0.0511 (18)	−0.0210 (13)	−0.0116 (12)	0.0060 (13)
C3	0.0384 (14)	0.0529 (18)	0.065 (2)	−0.0101 (14)	−0.0133 (14)	−0.0049 (15)
C4	0.0571 (17)	0.0424 (16)	0.071 (2)	−0.0112 (15)	−0.0320 (16)	0.0091 (15)
C5	0.0583 (16)	0.0459 (15)	0.0442 (17)	−0.0215 (14)	−0.0224 (14)	0.0122 (13)
C6	0.066 (2)	0.065 (2)	0.123 (4)	−0.0124 (19)	−0.061 (2)	−0.011 (2)
C7	0.143 (4)	0.124 (4)	0.089 (3)	−0.090 (3)	−0.087 (3)	0.050 (3)
C8	0.086 (3)	0.131 (4)	0.062 (3)	−0.058 (3)	−0.013 (2)	−0.030 (3)
C9	0.0600 (19)	0.061 (2)	0.100 (3)	−0.0257 (17)	−0.0199 (19)	−0.023 (2)
C10	0.0514 (17)	0.078 (2)	0.081 (3)	−0.0330 (18)	−0.0153 (17)	−0.0121 (19)
C11	0.0393 (13)	0.0392 (14)	0.0380 (15)	−0.0202 (11)	−0.0145 (12)	0.0032 (11)
C12	0.0373 (13)	0.0434 (15)	0.0432 (16)	−0.0184 (12)	−0.0109 (11)	0.0063 (12)
C13	0.0461 (14)	0.0382 (14)	0.0502 (18)	−0.0169 (12)	−0.0136 (13)	0.0034 (12)
C14	0.0323 (12)	0.0375 (14)	0.0425 (16)	−0.0076 (11)	−0.0070 (11)	0.0054 (11)
C15	0.0498 (16)	0.066 (2)	0.059 (2)	−0.0323 (15)	−0.0171 (15)	0.0151 (16)
C16	0.0664 (19)	0.092 (3)	0.050 (2)	−0.0414 (19)	−0.0132 (16)	0.0199 (18)
C17	0.070 (2)	0.096 (3)	0.044 (2)	−0.037 (2)	−0.0199 (16)	0.0094 (18)
C18	0.0460 (15)	0.069 (2)	0.057 (2)	−0.0261 (15)	−0.0169 (14)	0.0030 (16)
C19	0.0372 (13)	0.0527 (17)	0.0475 (18)	−0.0185 (13)	−0.0098 (12)	0.0090 (13)

Fe—C1	2.015 (3)	C6—C7	1.402 (5)
Fe—C5	2.021 (3)	C6—H6	0.9300
Fe—C7	2.023 (3)	C7—C8	1.405 (6)
Fe—C8	2.024 (4)	C7—H7	0.9300
Fe—C6	2.031 (3)	C8—C9	1.368 (5)
Fe—C2	2.036 (3)	C8—H8	0.9300
Fe—C10	2.042 (3)	C9—C10	1.398 (4)
Fe—C9	2.042 (3)	C9—H9	0.9300
Fe—C4	2.048 (3)	C10—H10	0.9300
Fe—C3	2.057 (3)	C11—C12	1.511 (3)
F1—C18	1.362 (3)	C12—C13	1.520 (3)
O1—C11	1.217 (3)	C12—H12A	0.9700
N1—C14	1.380 (4)	C12—H12B	0.9700
N1—C13	1.448 (3)	C13—H13A	0.9700
N1—H1N	0.83 (3)	C13—H13B	0.9700
C1—C5	1.432 (3)	C14—C19	1.392 (4)
C1—C2	1.432 (3)	C14—C15	1.397 (4)
C1—C11	1.467 (3)	C15—C16	1.385 (4)
C2—C3	1.412 (4)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.371 (4)
C3—C4	1.408 (4)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.359 (4)
C4—C5	1.399 (4)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.362 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—C10	1.401 (5)
C1—Fe—C5	41.55 (10)	Fe—C4—H4	127.0
C1—Fe—C7	121.77 (16)	C4—C5—C1	107.9 (2)
C5—Fe—C7	157.2 (2)	C4—C5—Fe	70.97 (17)
C1—Fe—C8	157.73 (16)	C1—C5—Fe	69.04 (15)
C5—Fe—C8	159.81 (17)	C4—C5—H5	126.1
C7—Fe—C8	40.61 (17)	C1—C5—H5	126.1
C1—Fe—C6	107.95 (13)	Fe—C5—H5	125.5
C5—Fe—C6	121.21 (15)	C10—C6—C7	108.0 (3)
C7—Fe—C6	40.47 (16)	C10—C6—Fe	70.29 (17)
C8—Fe—C6	67.65 (16)	C7—C6—Fe	69.46 (19)
C1—Fe—C2	41.40 (10)	C10—C6—H6	126.0
C5—Fe—C2	69.20 (11)	C7—C6—H6	126.0
C7—Fe—C2	108.79 (14)	Fe—C6—H6	125.8
C8—Fe—C2	122.24 (15)	C6—C7—C8	107.1 (3)
C6—Fe—C2	126.19 (13)	C6—C7—Fe	70.07 (19)
C1—Fe—C10	124.64 (12)	C8—C7—Fe	69.7 (2)
C5—Fe—C10	106.96 (13)	C6—C7—H7	126.5
C7—Fe—C10	67.81 (16)	C8—C7—H7	126.5
C8—Fe—C10	67.08 (15)	Fe—C7—H7	125.3
C6—Fe—C10	40.25 (13)	C9—C8—C7	108.8 (4)
C2—Fe—C10	162.67 (12)	C9—C8—Fe	71.0 (2)
C1—Fe—C9	161.18 (13)	C7—C8—Fe	69.6 (2)
C5—Fe—C9	123.84 (14)	C9—C8—H8	125.6
C7—Fe—C9	67.37 (16)	C7—C8—H8	125.6
C8—Fe—C9	39.32 (15)	Fe—C8—H8	125.3
C6—Fe—C9	67.32 (14)	C8—C9—C10	108.6 (4)
C2—Fe—C9	156.06 (13)	C8—C9—Fe	69.6 (2)
C10—Fe—C9	40.02 (13)	C10—C9—Fe	69.97 (19)
C1—Fe—C4	68.51 (11)	C8—C9—H9	125.7
C5—Fe—C4	40.20 (11)	C10—C9—H9	125.7
C7—Fe—C4	161.8 (2)	Fe—C9—H9	126.3
C8—Fe—C4	124.67 (16)	C9—C10—C6	107.5 (3)
C6—Fe—C4	155.86 (16)	C9—C10—Fe	70.01 (18)
C2—Fe—C4	67.94 (11)	C6—C10—Fe	69.46 (19)
C10—Fe—C4	120.74 (14)	C9—C10—H10	126.2
C9—Fe—C4	107.89 (14)	C6—C10—H10	126.2
C1—Fe—C3	68.74 (11)	Fe—C10—H10	125.9
C5—Fe—C3	68.21 (12)	O1—C11—C1	121.5 (2)
C7—Fe—C3	125.88 (17)	O1—C11—C12	121.0 (2)
C8—Fe—C3	108.67 (14)	C1—C11—C12	117.5 (2)
C6—Fe—C3	162.91 (15)	C11—C12—C13	112.7 (2)
C2—Fe—C3	40.37 (10)	C11—C12—H12A	109.1
C10—Fe—C3	155.42 (13)	C13—C12—H12A	109.1
C9—Fe—C3	121.22 (12)	C11—C12—H12B	109.1
C4—Fe—C3	40.10 (11)	C13—C12—H12B	109.1
C14—N1—C13	122.9 (2)	H12A—C12—H12B	107.8
C14—N1—H1N	114 (2)	N1—C13—C12	113.3 (2)
C13—N1—H1N	116.5 (18)	N1—C13—H13A	108.9
C5—C1—C2	107.1 (2)	C12—C13—H13A	108.9
C5—C1—C11	125.0 (2)	N1—C13—H13B	108.9
C2—C1—C11	127.6 (2)	C12—C13—H13B	108.9
C5—C1—Fe	69.42 (16)	H13A—C13—H13B	107.7
C2—C1—Fe	70.07 (15)	N1—C14—C19	119.0 (2)
C11—C1—Fe	121.02 (16)	N1—C14—C15	122.8 (3)
C3—C2—C1	107.8 (2)	C19—C14—C15	118.1 (3)
C3—C2—Fe	70.61 (16)	C16—C15—C14	119.8 (3)
C1—C2—Fe	68.53 (14)	C16—C15—H15	120.1
C3—C2—H2	126.1	C14—C15—H15	120.1
C1—C2—H2	126.1	C17—C16—C15	121.9 (3)
Fe—C2—H2	126.3	C17—C16—H16	119.1
C4—C3—C2	108.0 (2)	C15—C16—H16	119.1
C4—C3—Fe	69.62 (15)	C18—C17—C16	117.0 (3)
C2—C3—Fe	69.02 (14)	C18—C17—H17	121.5
C4—C3—H3	126.0	C16—C17—H17	121.5
C2—C3—H3	126.0	C17—C18—F1	118.7 (3)
Fe—C3—H3	127.0	C17—C18—C19	123.7 (3)
C5—C4—C3	109.1 (2)	F1—C18—C19	117.5 (3)
C5—C4—Fe	68.83 (15)	C18—C19—C14	119.5 (3)
C3—C4—Fe	70.28 (15)	C18—C19—H19	120.3
C5—C4—H4	125.4	C14—C19—H19	120.3
C3—C4—H4	125.4
C7—Fe—C1—C5	−159.4 (2)	C9—Fe—C6—C10	−37.7 (2)
C8—Fe—C1—C5	168.2 (3)	C4—Fe—C6—C10	45.5 (4)
C6—Fe—C1—C5	−117.1 (2)	C3—Fe—C6—C10	−161.3 (4)
C2—Fe—C1—C5	118.1 (2)	C1—Fe—C6—C7	−118.2 (3)
C10—Fe—C1—C5	−75.8 (2)	C5—Fe—C6—C7	−161.9 (2)
C9—Fe—C1—C5	−44.9 (4)	C8—Fe—C6—C7	38.5 (2)
C4—Fe—C1—C5	37.50 (16)	C2—Fe—C6—C7	−76.0 (3)
C3—Fe—C1—C5	80.70 (16)	C10—Fe—C6—C7	118.9 (3)
C5—Fe—C1—C2	−118.1 (2)	C9—Fe—C6—C7	81.2 (3)
C7—Fe—C1—C2	82.6 (2)	C4—Fe—C6—C7	164.4 (3)
C8—Fe—C1—C2	50.1 (4)	C3—Fe—C6—C7	−42.3 (6)
C6—Fe—C1—C2	124.83 (19)	C10—C6—C7—C8	−0.2 (4)
C10—Fe—C1—C2	166.12 (17)	Fe—C6—C7—C8	−60.2 (2)
C9—Fe—C1—C2	−163.0 (3)	C10—C6—C7—Fe	60.0 (2)
C4—Fe—C1—C2	−80.57 (16)	C1—Fe—C7—C6	80.4 (2)
C3—Fe—C1—C2	−37.36 (15)	C5—Fe—C7—C6	43.3 (5)
C5—Fe—C1—C11	119.3 (3)	C8—Fe—C7—C6	−117.8 (3)
C7—Fe—C1—C11	−40.1 (3)	C2—Fe—C7—C6	124.2 (2)
C8—Fe—C1—C11	−72.6 (4)	C10—Fe—C7—C6	−37.6 (2)
C6—Fe—C1—C11	2.1 (3)	C9—Fe—C7—C6	−81.1 (2)
C2—Fe—C1—C11	−122.7 (3)	C4—Fe—C7—C6	−159.4 (4)
C10—Fe—C1—C11	43.4 (3)	C3—Fe—C7—C6	165.9 (2)
C9—Fe—C1—C11	74.3 (4)	C1—Fe—C7—C8	−161.8 (2)
C4—Fe—C1—C11	156.7 (2)	C5—Fe—C7—C8	161.1 (3)
C3—Fe—C1—C11	−160.0 (2)	C6—Fe—C7—C8	117.8 (3)
C5—C1—C2—C3	0.1 (3)	C2—Fe—C7—C8	−118.0 (2)
C11—C1—C2—C3	174.3 (2)	C10—Fe—C7—C8	80.2 (3)
Fe—C1—C2—C3	59.91 (19)	C9—Fe—C7—C8	36.7 (2)
C5—C1—C2—Fe	−59.81 (18)	C4—Fe—C7—C8	−41.6 (6)
C11—C1—C2—Fe	114.4 (3)	C3—Fe—C7—C8	−76.3 (3)
C1—Fe—C2—C3	−119.2 (2)	C6—C7—C8—C9	−0.1 (4)
C5—Fe—C2—C3	−80.42 (18)	Fe—C7—C8—C9	−60.5 (3)
C7—Fe—C2—C3	123.8 (2)	C6—C7—C8—Fe	60.4 (2)
C8—Fe—C2—C3	80.9 (2)	C1—Fe—C8—C9	163.9 (3)
C6—Fe—C2—C3	165.4 (2)	C5—Fe—C8—C9	−39.3 (5)
C10—Fe—C2—C3	−160.7 (4)	C7—Fe—C8—C9	119.4 (3)
C9—Fe—C2—C3	47.4 (4)	C6—Fe—C8—C9	81.0 (2)
C4—Fe—C2—C3	−37.11 (17)	C2—Fe—C8—C9	−159.27 (18)
C5—Fe—C2—C1	38.76 (14)	C10—Fe—C8—C9	37.3 (2)
C7—Fe—C2—C1	−117.1 (2)	C4—Fe—C8—C9	−75.2 (3)
C8—Fe—C2—C1	−159.89 (19)	C3—Fe—C8—C9	−116.8 (2)
C6—Fe—C2—C1	−75.4 (2)	C1—Fe—C8—C7	44.5 (5)
C10—Fe—C2—C1	−41.5 (5)	C5—Fe—C8—C7	−158.7 (4)
C9—Fe—C2—C1	166.5 (3)	C6—Fe—C8—C7	−38.4 (2)
C4—Fe—C2—C1	82.07 (16)	C2—Fe—C8—C7	81.3 (3)
C3—Fe—C2—C1	119.2 (2)	C10—Fe—C8—C7	−82.1 (3)
C1—C2—C3—C4	0.2 (3)	C9—Fe—C8—C7	−119.4 (3)
Fe—C2—C3—C4	58.9 (2)	C4—Fe—C8—C7	165.4 (2)
C1—C2—C3—Fe	−58.60 (18)	C3—Fe—C8—C7	123.8 (3)
C1—Fe—C3—C4	−81.48 (19)	C7—C8—C9—C10	0.4 (4)
C5—Fe—C3—C4	−36.66 (18)	Fe—C8—C9—C10	−59.3 (2)
C7—Fe—C3—C4	164.0 (2)	C7—C8—C9—Fe	59.6 (3)
C8—Fe—C3—C4	122.1 (2)	C1—Fe—C9—C8	−160.9 (3)
C6—Fe—C3—C4	−163.4 (5)	C5—Fe—C9—C8	164.7 (2)
C2—Fe—C3—C4	−119.8 (3)	C7—Fe—C9—C8	−37.9 (2)
C10—Fe—C3—C4	46.5 (4)	C6—Fe—C9—C8	−81.9 (3)
C9—Fe—C3—C4	80.7 (2)	C2—Fe—C9—C8	47.5 (4)
C1—Fe—C3—C2	38.28 (16)	C10—Fe—C9—C8	−119.9 (3)
C5—Fe—C3—C2	83.11 (18)	C4—Fe—C9—C8	123.3 (2)
C7—Fe—C3—C2	−76.3 (3)	C3—Fe—C9—C8	81.4 (3)
C8—Fe—C3—C2	−118.2 (2)	C1—Fe—C9—C10	−41.1 (5)
C6—Fe—C3—C2	−43.6 (5)	C5—Fe—C9—C10	−75.4 (3)
C10—Fe—C3—C2	166.3 (3)	C7—Fe—C9—C10	82.0 (3)
C9—Fe—C3—C2	−159.6 (2)	C8—Fe—C9—C10	119.9 (3)
C4—Fe—C3—C2	119.8 (3)	C6—Fe—C9—C10	37.9 (2)
C2—C3—C4—C5	−0.5 (3)	C2—Fe—C9—C10	167.4 (3)
Fe—C3—C4—C5	58.0 (2)	C4—Fe—C9—C10	−116.8 (2)
C2—C3—C4—Fe	−58.5 (2)	C3—Fe—C9—C10	−158.7 (2)
C1—Fe—C4—C5	−38.72 (16)	C8—C9—C10—C6	−0.5 (4)
C7—Fe—C4—C5	−166.6 (4)	Fe—C9—C10—C6	−59.6 (2)
C8—Fe—C4—C5	161.7 (2)	C8—C9—C10—Fe	59.1 (2)
C6—Fe—C4—C5	47.3 (4)	C7—C6—C10—C9	0.4 (4)
C2—Fe—C4—C5	−83.46 (18)	Fe—C6—C10—C9	59.9 (2)
C10—Fe—C4—C5	79.8 (2)	C7—C6—C10—Fe	−59.5 (2)
C9—Fe—C4—C5	121.65 (19)	C1—Fe—C10—C9	165.1 (2)
C3—Fe—C4—C5	−120.8 (3)	C5—Fe—C10—C9	122.8 (2)
C1—Fe—C4—C3	82.09 (18)	C7—Fe—C10—C9	−80.8 (3)
C5—Fe—C4—C3	120.8 (3)	C8—Fe—C10—C9	−36.6 (2)
C7—Fe—C4—C3	−45.8 (5)	C6—Fe—C10—C9	−118.6 (3)
C8—Fe—C4—C3	−77.5 (2)	C2—Fe—C10—C9	−162.7 (4)
C6—Fe—C4—C3	168.2 (3)	C4—Fe—C10—C9	81.2 (3)
C2—Fe—C4—C3	37.35 (18)	C3—Fe—C10—C9	48.3 (4)
C10—Fe—C4—C3	−159.44 (18)	C1—Fe—C10—C6	−76.3 (3)
C9—Fe—C4—C3	−117.5 (2)	C5—Fe—C10—C6	−118.6 (2)
C3—C4—C5—C1	0.6 (3)	C7—Fe—C10—C6	37.8 (2)
Fe—C4—C5—C1	59.42 (18)	C8—Fe—C10—C6	82.0 (3)
C3—C4—C5—Fe	−58.8 (2)	C2—Fe—C10—C6	−44.1 (5)
C2—C1—C5—C4	−0.4 (3)	C9—Fe—C10—C6	118.6 (3)
C11—C1—C5—C4	−174.8 (2)	C4—Fe—C10—C6	−160.2 (2)
Fe—C1—C5—C4	−60.6 (2)	C3—Fe—C10—C6	166.9 (3)
C2—C1—C5—Fe	60.22 (18)	C5—C1—C11—O1	−3.5 (4)
C11—C1—C5—Fe	−114.1 (2)	C2—C1—C11—O1	−176.7 (3)
C1—Fe—C5—C4	118.7 (2)	Fe—C1—C11—O1	−88.9 (3)
C7—Fe—C5—C4	169.2 (3)	C5—C1—C11—C12	178.2 (2)
C8—Fe—C5—C4	−48.4 (4)	C2—C1—C11—C12	5.0 (4)
C6—Fe—C5—C4	−159.41 (19)	Fe—C1—C11—C12	92.8 (2)
C2—Fe—C5—C4	80.03 (18)	O1—C11—C12—C13	12.5 (4)
C10—Fe—C5—C4	−117.84 (19)	C1—C11—C12—C13	−169.1 (2)
C9—Fe—C5—C4	−77.3 (2)	C14—N1—C13—C12	72.1 (3)
C3—Fe—C5—C4	36.57 (17)	C11—C12—C13—N1	71.8 (3)
C7—Fe—C5—C1	50.6 (4)	C13—N1—C14—C19	−167.6 (2)
C8—Fe—C5—C1	−167.0 (3)	C13—N1—C14—C15	15.9 (4)
C6—Fe—C5—C1	81.9 (2)	N1—C14—C15—C16	174.8 (3)
C2—Fe—C5—C1	−38.62 (14)	C19—C14—C15—C16	−1.7 (4)
C10—Fe—C5—C1	123.50 (17)	C14—C15—C16—C17	0.8 (5)
C9—Fe—C5—C1	164.08 (15)	C15—C16—C17—C18	0.2 (5)
C4—Fe—C5—C1	−118.7 (2)	C16—C17—C18—F1	−179.4 (3)
C3—Fe—C5—C1	−82.09 (16)	C16—C17—C18—C19	−0.2 (5)
C1—Fe—C6—C10	122.8 (2)	C17—C18—C19—C14	−0.7 (5)
C5—Fe—C6—C10	79.2 (2)	F1—C18—C19—C14	178.5 (3)
C7—Fe—C6—C10	−118.9 (3)	N1—C14—C19—C18	−175.0 (2)
C8—Fe—C6—C10	−80.4 (3)	C15—C14—C19—C18	1.6 (4)
C2—Fe—C6—C10	165.10 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (3)	2.24 (3)	3.049 (3)	165 (3)
C19—H19···O1i	0.93	2.57	3.342 (3)	141
C4—H4···N1ii	0.93	2.66	3.517 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.83 (3)	2.24 (3)	3.049 (3)	165 (3)
C19—H19⋯O1i	0.93	2.57	3.342 (3)	141
C4—H4⋯N1ii	0.93	2.66	3.517 (3)	153

Symmetry codes: (i) ; (ii) .