1′-(1-Hydro­xy­ethyl)-N,N-di­phenyl­ferrocene-1-carbox­amide

In the title compound, [Fe(C₁₈H₁₄NO)(C₇H₉O)], an N,N-di­phenyl­carbox­amide moiety and a hydroxy­ethyl group are attached to the ferrocene skeleton. The cyclo­penta­dienyl rings deviate only slightly from an eclipsed conformation. Two C—H...π interactions link the mol­ecules into sheets. According to the X-ray, IR, and ¹H NMR data, the mol­ecule also possesses an intramolecular O—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.066
• wR factor = 0.169
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found





Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H19    ..  CG2     ..       3.25 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H19    ..  C6      ..       3.36 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H2A    ..  CG3     ..       3.20 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H2A    ..  C18     ..       3.20 Ang.

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.97 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19    ..  C10     ..       3.09 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A    ..  C23     ..       2.93 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C19    ..  CG2     ..       3.93 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C19    ..  C10     ..       3.93 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C19    ..  C6      ..       4.01 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C2     ..  CG3     ..       3.91 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C2     ..  C18     ..       4.07 Ang.

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
   9 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
   1 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
  11 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

1'-(1-Hydroxyethyl)-N,N-diphenylferrocene-1-carboxamide

Crystal data

[Fe(C18H14NO)(C7H9O)]	F(000) = 888
Mr = 425.29	Dx = 1.407 Mg m^−3
Monoclinic, P21/c	Melting point = 386–388 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.0428 (12) Å	Cell parameters from 3736 reflections
b = 18.507 (2) Å	θ = 11.1–20.6°
c = 10.1462 (11) Å	µ = 0.77 mm^−1
β = 104.547 (9)°	T = 293 K
V = 2007.0 (4) Å^3	Prism, orange
Z = 4	0.45 × 0.24 × 0.13 mm

Data collection

Oxford Diffraction Xcalibur2 diffractometer	3473 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
Graphite monochromator	θmax = 26.0°, θmin = 4.0°
ω scans	h = −13→13
Absorption correction: numerical (CrysAlis RED; Oxford Diffraction, 2004)	k = −22→19
Tmin = 0.775, Tmax = 0.906	l = −12→12
16741 measured reflections	Standard reflections: 2 frames; every 50 frames reflections
3929 independent reflections	intensity decay: none

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H-atom parameters constrained
S = 1.17	w = 1/[σ^2(Fo^2) + (0.0814P)^2 + 1.0597P] where P = (Fo^2 + 2Fc^2)/3
3929 reflections	(Δ/σ)max = 0.001
263 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

Experimental. Melting points were determined with a Buechi apparatus. The IR spectra were recorded in CH₂Cl₂ on a Bomem MB100 Mid FT IR spectrophotometer. The ¹H and ¹³C NMR spectra in CDCl₃ were recorded on a Varian Gemini 300 spectrometer with tetramethylsilane as internal standard.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Fe	0.24221 (4)	0.59575 (3)	0.76272 (5)	0.0402 (2)
N1	−0.0867 (3)	0.61967 (16)	0.9048 (3)	0.0427 (7)
O1	0.0732 (2)	0.70061 (14)	0.9403 (3)	0.0563 (7)
O2	0.2841 (4)	0.77979 (19)	0.8974 (5)	0.0985 (13)
H2	0.2314	0.7496	0.9035	0.148*
C1	0.0612 (3)	0.61487 (19)	0.7633 (4)	0.0400 (8)
C2	0.0785 (3)	0.5400 (2)	0.7419 (4)	0.0483 (9)
H2A	0.0640	0.5023	0.7966	0.058*
C3	0.1220 (4)	0.5331 (2)	0.6217 (4)	0.0549 (10)
H3	0.1416	0.4900	0.5844	0.066*
C4	0.1302 (4)	0.6023 (2)	0.5698 (4)	0.0581 (11)
H4	0.1553	0.6129	0.4911	0.070*
C5	0.0942 (4)	0.6539 (2)	0.6560 (4)	0.0511 (9)
H5	0.0923	0.7038	0.6448	0.061*
C6	0.3776 (4)	0.6694 (2)	0.8395 (4)	0.0578 (10)
C7	0.3543 (4)	0.6252 (3)	0.9461 (4)	0.0562 (10)
H7	0.3291	0.6420	1.0214	0.067*
C8	0.3756 (4)	0.5521 (3)	0.9192 (5)	0.0640 (11)
H8	0.3654	0.5126	0.9721	0.077*
C9	0.4156 (4)	0.5497 (3)	0.7962 (5)	0.0676 (13)
H9	0.4365	0.5085	0.7544	0.081*
C10	0.4175 (4)	0.6215 (3)	0.7493 (5)	0.0637 (11)
H10	0.4413	0.6353	0.6714	0.076*
C11	0.0184 (3)	0.64925 (18)	0.8771 (4)	0.0402 (8)
C12	−0.1694 (3)	0.5749 (2)	0.8045 (4)	0.0425 (8)
C13	−0.1895 (4)	0.5040 (2)	0.8342 (4)	0.0516 (9)
H13	−0.1503	0.4849	0.9189	0.062*
C14	−0.2684 (4)	0.4613 (3)	0.7375 (5)	0.0631 (12)
H14	−0.2820	0.4133	0.7569	0.076*
C15	−0.3265 (4)	0.4901 (3)	0.6125 (5)	0.0654 (12)
H15	−0.3787	0.4613	0.5471	0.078*
C16	−0.3081 (4)	0.5609 (3)	0.5838 (4)	0.0621 (11)
H16	−0.3485	0.5801	0.4994	0.075*
C17	−0.2295 (4)	0.6042 (2)	0.6800 (4)	0.0535 (10)
H17	−0.2173	0.6525	0.6609	0.064*
C18	−0.1293 (3)	0.64083 (18)	1.0227 (3)	0.0394 (8)
C19	−0.2564 (4)	0.6454 (2)	1.0121 (4)	0.0574 (10)
H19	−0.3132	0.6376	0.9287	0.069*
C20	−0.2987 (4)	0.6616 (3)	1.1259 (5)	0.0719 (13)
H20	−0.3842	0.6639	1.1190	0.086*
C21	−0.2152 (5)	0.6745 (3)	1.2494 (4)	0.0645 (12)
H21	−0.2439	0.6863	1.3253	0.077*
C22	−0.0898 (4)	0.6695 (2)	1.2592 (4)	0.0561 (10)
H22	−0.0331	0.6779	1.3426	0.067*
C23	−0.0460 (4)	0.6522 (2)	1.1467 (4)	0.0474 (9)
H23	0.0396	0.6482	1.1550	0.057*
C24	0.3638 (5)	0.7508 (3)	0.8218 (6)	0.0769 (14)
H24	0.3266	0.7608	0.7253	0.092*
C25	0.4815 (5)	0.7888 (3)	0.8617 (9)	0.116 (3)
H25A	0.4673	0.8397	0.8474	0.174*
H25B	0.5361	0.7720	0.8080	0.174*
H25C	0.5195	0.7799	0.9563	0.174*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe	0.0359 (3)	0.0444 (3)	0.0413 (3)	0.0026 (2)	0.0115 (2)	0.0011 (2)
N1	0.0384 (15)	0.0486 (16)	0.0428 (16)	−0.0036 (13)	0.0132 (13)	−0.0086 (13)
O1	0.0542 (16)	0.0504 (15)	0.0695 (18)	−0.0124 (13)	0.0249 (14)	−0.0158 (14)
O2	0.099 (3)	0.066 (2)	0.152 (4)	−0.0164 (19)	0.072 (3)	−0.023 (2)
C1	0.0345 (17)	0.0453 (19)	0.0402 (18)	0.0025 (14)	0.0092 (15)	−0.0049 (15)
C2	0.0427 (19)	0.046 (2)	0.059 (2)	−0.0025 (16)	0.0181 (17)	−0.0076 (18)
C3	0.045 (2)	0.063 (3)	0.056 (2)	0.0017 (18)	0.0105 (18)	−0.014 (2)
C4	0.052 (2)	0.088 (3)	0.0363 (19)	0.017 (2)	0.0147 (17)	0.001 (2)
C5	0.049 (2)	0.053 (2)	0.052 (2)	0.0122 (17)	0.0155 (18)	0.0117 (18)
C6	0.046 (2)	0.063 (3)	0.067 (3)	−0.0117 (19)	0.020 (2)	−0.014 (2)
C7	0.040 (2)	0.080 (3)	0.046 (2)	−0.0042 (19)	0.0059 (17)	−0.011 (2)
C8	0.050 (2)	0.073 (3)	0.064 (3)	0.011 (2)	0.002 (2)	0.011 (2)
C9	0.039 (2)	0.080 (3)	0.081 (3)	0.018 (2)	0.010 (2)	−0.015 (3)
C10	0.047 (2)	0.080 (3)	0.072 (3)	−0.006 (2)	0.028 (2)	−0.009 (2)
C11	0.0389 (18)	0.0386 (18)	0.0436 (18)	0.0023 (14)	0.0113 (15)	−0.0005 (15)
C12	0.0319 (16)	0.053 (2)	0.0424 (19)	−0.0021 (15)	0.0100 (14)	−0.0094 (16)
C13	0.048 (2)	0.056 (2)	0.052 (2)	−0.0071 (17)	0.0127 (18)	−0.0035 (18)
C14	0.059 (3)	0.061 (3)	0.072 (3)	−0.016 (2)	0.020 (2)	−0.017 (2)
C15	0.047 (2)	0.090 (3)	0.058 (3)	−0.011 (2)	0.011 (2)	−0.031 (2)
C16	0.050 (2)	0.090 (3)	0.042 (2)	0.008 (2)	0.0035 (18)	−0.004 (2)
C17	0.046 (2)	0.061 (2)	0.053 (2)	0.0060 (18)	0.0103 (18)	−0.0026 (19)
C18	0.0412 (18)	0.0386 (18)	0.0400 (18)	0.0009 (14)	0.0131 (15)	−0.0018 (14)
C19	0.041 (2)	0.083 (3)	0.049 (2)	0.0038 (19)	0.0127 (17)	−0.013 (2)
C20	0.050 (2)	0.107 (4)	0.063 (3)	0.007 (2)	0.022 (2)	−0.016 (3)
C21	0.074 (3)	0.073 (3)	0.055 (3)	0.007 (2)	0.032 (2)	−0.007 (2)
C22	0.070 (3)	0.056 (2)	0.039 (2)	−0.003 (2)	0.0071 (19)	−0.0006 (18)
C23	0.044 (2)	0.049 (2)	0.046 (2)	−0.0017 (16)	0.0061 (16)	0.0006 (17)
C24	0.070 (3)	0.059 (3)	0.108 (4)	−0.014 (2)	0.035 (3)	−0.012 (3)
C25	0.073 (4)	0.077 (4)	0.206 (8)	−0.010 (3)	0.046 (4)	0.019 (4)

Geometric parameters (Å, º)

Fe—C6	2.029 (4)	C8—H8	0.9300
Fe—C1	2.032 (3)	C9—C10	1.413 (7)
Fe—C5	2.029 (4)	C9—H9	0.9300
Fe—C10	2.031 (4)	C10—H10	0.9300
Fe—C7	2.033 (4)	C12—C13	1.376 (5)
Fe—C8	2.042 (4)	C12—C17	1.382 (5)
Fe—C9	2.044 (4)	C13—C14	1.385 (6)
Fe—C2	2.046 (4)	C13—H13	0.9300
Fe—C4	2.040 (4)	C14—C15	1.378 (6)
Fe—C3	2.049 (4)	C14—H14	0.9300
N1—C11	1.374 (4)	C15—C16	1.369 (7)
N1—C12	1.446 (4)	C15—H15	0.9300
N1—C18	1.445 (4)	C16—C17	1.387 (6)
O1—C11	1.219 (4)	C16—H16	0.9300
O2—C24	1.411 (6)	C17—H17	0.9300
O2—H2	0.8200	C18—C23	1.376 (5)
C1—C2	1.424 (5)	C18—C19	1.383 (5)
C1—C5	1.428 (5)	C19—C20	1.383 (6)
C1—C11	1.495 (5)	C19—H19	0.9300
C2—C3	1.424 (5)	C20—C21	1.376 (6)
C2—H2A	0.9300	C20—H20	0.9300
C3—C4	1.397 (6)	C21—C22	1.367 (6)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.418 (6)	C22—C23	1.385 (5)
C4—H4	0.9300	C22—H22	0.9300
C5—H5	0.9300	C23—H23	0.9300
C6—C10	1.421 (6)	C24—C25	1.443 (7)
C6—C7	1.430 (6)	C24—H24	0.9800
C6—C24	1.520 (7)	C25—H25A	0.9600
C7—C8	1.412 (6)	C25—H25B	0.9600
C7—H7	0.9300	C25—H25C	0.9600
C8—C9	1.425 (7)
C6—Fe—C1	120.83 (16)	C10—C6—C24	125.4 (4)
C6—Fe—C5	105.41 (18)	C7—C6—C24	128.7 (4)
C1—Fe—C5	41.19 (15)	C10—C6—Fe	69.6 (2)
C6—Fe—C10	40.98 (17)	C7—C6—Fe	69.6 (2)
C1—Fe—C10	156.11 (18)	C24—C6—Fe	125.3 (3)
C5—Fe—C10	119.58 (19)	C8—C7—C6	109.4 (4)
C6—Fe—C7	41.22 (17)	C8—C7—Fe	70.1 (2)
C1—Fe—C7	108.91 (15)	C6—C7—Fe	69.2 (2)
C5—Fe—C7	124.76 (17)	C8—C7—H7	125.3
C10—Fe—C7	68.08 (18)	C6—C7—H7	125.3
C6—Fe—C8	69.46 (19)	Fe—C7—H7	127.0
C1—Fe—C8	125.79 (17)	C9—C8—C7	107.6 (4)
C5—Fe—C8	162.26 (18)	C9—C8—Fe	69.7 (2)
C10—Fe—C8	68.4 (2)	C7—C8—Fe	69.4 (2)
C7—Fe—C8	40.53 (18)	C9—C8—H8	126.2
C6—Fe—C9	69.34 (19)	C7—C8—H8	126.2
C1—Fe—C9	162.39 (19)	Fe—C8—H8	126.3
C5—Fe—C9	154.87 (19)	C8—C9—C10	107.5 (4)
C10—Fe—C9	40.58 (19)	C8—C9—Fe	69.5 (2)
C7—Fe—C9	68.28 (18)	C10—C9—Fe	69.2 (2)
C8—Fe—C9	40.82 (19)	C8—C9—H9	126.3
C6—Fe—C2	157.74 (16)	C10—C9—H9	126.3
C1—Fe—C2	40.86 (14)	Fe—C9—H9	126.6
C5—Fe—C2	68.89 (16)	C6—C10—C9	109.7 (4)
C10—Fe—C2	160.69 (17)	C6—C10—Fe	69.4 (2)
C7—Fe—C2	123.29 (17)	C9—C10—Fe	70.2 (2)
C8—Fe—C2	109.07 (18)	C6—C10—H10	125.2
C9—Fe—C2	124.97 (19)	C9—C10—H10	125.2
C6—Fe—C4	122.63 (19)	Fe—C10—H10	126.8
C1—Fe—C4	68.44 (15)	O1—C11—N1	122.4 (3)
C5—Fe—C4	40.78 (16)	O1—C11—C1	121.8 (3)
C10—Fe—C4	106.27 (19)	N1—C11—C1	115.8 (3)
C7—Fe—C4	160.95 (19)	C13—C12—C17	120.5 (3)
C8—Fe—C4	156.21 (18)	C13—C12—N1	120.0 (3)
C9—Fe—C4	120.08 (18)	C17—C12—N1	119.4 (3)
C2—Fe—C4	67.91 (17)	C12—C13—C14	119.8 (4)
C6—Fe—C3	159.07 (18)	C12—C13—H13	120.1
C1—Fe—C3	68.63 (15)	C14—C13—H13	120.1
C5—Fe—C3	68.53 (17)	C15—C14—C13	119.7 (4)
C10—Fe—C3	123.17 (18)	C15—C14—H14	120.2
C7—Fe—C3	158.31 (18)	C13—C14—H14	120.2
C8—Fe—C3	122.21 (19)	C16—C15—C14	120.5 (4)
C9—Fe—C3	107.17 (18)	C16—C15—H15	119.8
C2—Fe—C3	40.70 (15)	C14—C15—H15	119.8
C4—Fe—C3	39.97 (17)	C15—C16—C17	120.3 (4)
C11—N1—C12	120.1 (3)	C15—C16—H16	119.9
C11—N1—C18	121.9 (3)	C17—C16—H16	119.9
C12—N1—C18	117.3 (3)	C12—C17—C16	119.2 (4)
C24—O2—H2	109.5	C12—C17—H17	120.4
C2—C1—C5	107.8 (3)	C16—C17—H17	120.4
C2—C1—C11	127.8 (3)	C23—C18—C19	119.6 (3)
C5—C1—C11	124.3 (3)	C23—C18—N1	121.1 (3)
C2—C1—Fe	70.1 (2)	C19—C18—N1	119.2 (3)
C5—C1—Fe	69.3 (2)	C18—C19—C20	119.9 (4)
C11—C1—Fe	125.3 (2)	C18—C19—H19	120.1
C1—C2—C3	107.8 (3)	C20—C19—H19	120.1
C1—C2—Fe	69.0 (2)	C21—C20—C19	120.5 (4)
C3—C2—Fe	69.8 (2)	C21—C20—H20	119.7
C1—C2—H2A	126.1	C19—C20—H20	119.7
C3—C2—H2A	126.1	C22—C21—C20	119.3 (4)
Fe—C2—H2A	126.6	C22—C21—H21	120.3
C4—C3—C2	107.9 (4)	C20—C21—H21	120.3
C4—C3—Fe	69.6 (2)	C21—C22—C23	120.8 (4)
C2—C3—Fe	69.5 (2)	C21—C22—H22	119.6
C4—C3—H3	126.0	C23—C22—H22	119.6
C2—C3—H3	126.0	C18—C23—C22	119.8 (4)
Fe—C3—H3	126.4	C18—C23—H23	120.1
C3—C4—C5	109.3 (4)	C22—C23—H23	120.1
C3—C4—Fe	70.4 (2)	O2—C24—C25	107.7 (5)
C5—C4—Fe	69.2 (2)	O2—C24—C6	111.7 (4)
C3—C4—H4	125.4	C25—C24—C6	113.1 (5)
C5—C4—H4	125.3	O2—C24—H24	108.1
Fe—C4—H4	126.7	C25—C24—H24	108.1
C4—C5—C1	107.1 (3)	C6—C24—H24	108.1
C4—C5—Fe	70.0 (2)	C24—C25—H25A	109.5
C1—C5—Fe	69.5 (2)	C24—C25—H25B	109.5
C4—C5—H5	126.4	H25A—C25—H25B	109.5
C1—C5—H5	126.4	C24—C25—H25C	109.5
Fe—C5—H5	125.6	H25A—C25—H25C	109.5
C10—C6—C7	105.9 (4)	H25B—C25—H25C	109.5
C6—Fe—C1—C2	−163.2 (2)	C8—Fe—C6—C24	−160.1 (4)
C5—Fe—C1—C2	119.0 (3)	C9—Fe—C6—C24	156.2 (5)
C10—Fe—C1—C2	162.2 (4)	C2—Fe—C6—C24	−69.7 (6)
C7—Fe—C1—C2	−119.4 (2)	C4—Fe—C6—C24	42.9 (4)
C8—Fe—C1—C2	−77.4 (3)	C3—Fe—C6—C24	72.1 (6)
C9—Fe—C1—C2	−41.7 (6)	C10—C6—C7—C8	−1.8 (5)
C4—Fe—C1—C2	80.7 (2)	C24—C6—C7—C8	178.1 (4)
C3—Fe—C1—C2	37.6 (2)	Fe—C6—C7—C8	58.6 (3)
C6—Fe—C1—C5	77.8 (3)	C10—C6—C7—Fe	−60.5 (3)
C10—Fe—C1—C5	43.2 (5)	C24—C6—C7—Fe	119.5 (5)
C7—Fe—C1—C5	121.6 (2)	C6—Fe—C7—C8	−121.1 (4)
C8—Fe—C1—C5	163.6 (3)	C1—Fe—C7—C8	123.4 (3)
C9—Fe—C1—C5	−160.8 (5)	C5—Fe—C7—C8	166.5 (3)
C2—Fe—C1—C5	−119.0 (3)	C10—Fe—C7—C8	−81.9 (3)
C4—Fe—C1—C5	−38.3 (2)	C9—Fe—C7—C8	−38.0 (3)
C3—Fe—C1—C5	−81.4 (3)	C2—Fe—C7—C8	80.4 (3)
C6—Fe—C1—C11	−40.3 (4)	C4—Fe—C7—C8	−158.0 (5)
C5—Fe—C1—C11	−118.1 (4)	C3—Fe—C7—C8	43.8 (5)
C10—Fe—C1—C11	−74.9 (5)	C1—Fe—C7—C6	−115.5 (2)
C7—Fe—C1—C11	3.5 (3)	C5—Fe—C7—C6	−72.5 (3)
C8—Fe—C1—C11	45.5 (4)	C10—Fe—C7—C6	39.1 (3)
C9—Fe—C1—C11	81.1 (6)	C8—Fe—C7—C6	121.1 (4)
C2—Fe—C1—C11	122.9 (4)	C9—Fe—C7—C6	83.0 (3)
C4—Fe—C1—C11	−156.4 (4)	C2—Fe—C7—C6	−158.5 (2)
C3—Fe—C1—C11	160.5 (3)	C4—Fe—C7—C6	−37.0 (6)
C5—C1—C2—C3	0.0 (4)	C3—Fe—C7—C6	164.9 (4)
C11—C1—C2—C3	−179.1 (3)	C6—C7—C8—C9	1.3 (5)
Fe—C1—C2—C3	−59.2 (3)	Fe—C7—C8—C9	59.5 (3)
C5—C1—C2—Fe	59.2 (3)	C6—C7—C8—Fe	−58.1 (3)
C11—C1—C2—Fe	−119.8 (4)	C6—Fe—C8—C9	−81.8 (3)
C6—Fe—C2—C1	40.9 (5)	C1—Fe—C8—C9	164.3 (3)
C5—Fe—C2—C1	−38.1 (2)	C5—Fe—C8—C9	−157.9 (5)
C10—Fe—C2—C1	−158.0 (5)	C10—Fe—C8—C9	−37.7 (3)
C7—Fe—C2—C1	80.4 (3)	C7—Fe—C8—C9	−118.9 (4)
C8—Fe—C2—C1	123.1 (2)	C2—Fe—C8—C9	121.8 (3)
C9—Fe—C2—C1	165.8 (2)	C4—Fe—C8—C9	43.5 (6)
C4—Fe—C2—C1	−82.1 (2)	C3—Fe—C8—C9	78.7 (3)
C3—Fe—C2—C1	−119.3 (3)	C6—Fe—C8—C7	37.1 (3)
C6—Fe—C2—C3	160.2 (4)	C1—Fe—C8—C7	−76.8 (3)
C1—Fe—C2—C3	119.3 (3)	C5—Fe—C8—C7	−39.1 (7)
C5—Fe—C2—C3	81.2 (3)	C10—Fe—C8—C7	81.1 (3)
C10—Fe—C2—C3	−38.7 (6)	C9—Fe—C8—C7	118.9 (4)
C7—Fe—C2—C3	−160.3 (2)	C2—Fe—C8—C7	−119.3 (3)
C8—Fe—C2—C3	−117.6 (3)	C4—Fe—C8—C7	162.4 (4)
C9—Fe—C2—C3	−74.9 (3)	C3—Fe—C8—C7	−162.4 (2)
C4—Fe—C2—C3	37.2 (2)	C7—C8—C9—C10	−0.3 (5)
C1—C2—C3—C4	−0.5 (4)	Fe—C8—C9—C10	59.0 (3)
Fe—C2—C3—C4	−59.3 (3)	C7—C8—C9—Fe	−59.3 (3)
C1—C2—C3—Fe	58.8 (3)	C6—Fe—C9—C8	82.1 (3)
C6—Fe—C3—C4	−39.7 (6)	C1—Fe—C9—C8	−46.4 (7)
C1—Fe—C3—C4	81.5 (2)	C5—Fe—C9—C8	164.4 (4)
C5—Fe—C3—C4	37.1 (2)	C10—Fe—C9—C8	119.0 (4)
C10—Fe—C3—C4	−75.0 (3)	C7—Fe—C9—C8	37.8 (3)
C7—Fe—C3—C4	169.1 (4)	C2—Fe—C9—C8	−78.5 (3)
C8—Fe—C3—C4	−158.8 (3)	C4—Fe—C9—C8	−161.3 (3)
C9—Fe—C3—C4	−116.6 (3)	C3—Fe—C9—C8	−119.7 (3)
C2—Fe—C3—C4	119.3 (3)	C6—Fe—C9—C10	−36.9 (3)
C6—Fe—C3—C2	−158.9 (4)	C1—Fe—C9—C10	−165.4 (5)
C1—Fe—C3—C2	−37.8 (2)	C5—Fe—C9—C10	45.4 (5)
C5—Fe—C3—C2	−82.2 (2)	C7—Fe—C9—C10	−81.2 (3)
C10—Fe—C3—C2	165.7 (2)	C8—Fe—C9—C10	−119.0 (4)
C7—Fe—C3—C2	49.8 (5)	C2—Fe—C9—C10	162.5 (3)
C8—Fe—C3—C2	81.9 (3)	C4—Fe—C9—C10	79.7 (3)
C9—Fe—C3—C2	124.1 (3)	C3—Fe—C9—C10	121.3 (3)
C4—Fe—C3—C2	−119.3 (3)	C7—C6—C10—C9	1.7 (5)
C2—C3—C4—C5	0.8 (5)	C24—C6—C10—C9	−178.3 (4)
Fe—C3—C4—C5	−58.4 (3)	Fe—C6—C10—C9	−58.8 (3)
C2—C3—C4—Fe	59.2 (3)	C7—C6—C10—Fe	60.4 (3)
C6—Fe—C4—C3	164.3 (2)	C24—C6—C10—Fe	−119.5 (4)
C1—Fe—C4—C3	−82.0 (2)	C8—C9—C10—C6	−0.9 (5)
C5—Fe—C4—C3	−120.7 (4)	Fe—C9—C10—C6	58.3 (3)
C10—Fe—C4—C3	122.6 (3)	C8—C9—C10—Fe	−59.2 (3)
C7—Fe—C4—C3	−167.6 (4)	C1—Fe—C10—C6	48.0 (5)
C8—Fe—C4—C3	49.5 (6)	C5—Fe—C10—C6	79.2 (3)
C9—Fe—C4—C3	80.8 (3)	C7—Fe—C10—C6	−39.4 (3)
C2—Fe—C4—C3	−37.9 (2)	C8—Fe—C10—C6	−83.2 (3)
C6—Fe—C4—C5	−75.0 (3)	C9—Fe—C10—C6	−121.1 (4)
C1—Fe—C4—C5	38.7 (2)	C2—Fe—C10—C6	−169.2 (5)
C10—Fe—C4—C5	−116.7 (3)	C4—Fe—C10—C6	121.4 (3)
C7—Fe—C4—C5	−46.9 (6)	C3—Fe—C10—C6	161.6 (3)
C8—Fe—C4—C5	170.2 (4)	C6—Fe—C10—C9	121.1 (4)
C9—Fe—C4—C5	−158.5 (3)	C1—Fe—C10—C9	169.1 (3)
C2—Fe—C4—C5	82.9 (3)	C5—Fe—C10—C9	−159.7 (3)
C3—Fe—C4—C5	120.7 (4)	C7—Fe—C10—C9	81.8 (3)
C3—C4—C5—C1	−0.8 (5)	C8—Fe—C10—C9	38.0 (3)
Fe—C4—C5—C1	−59.9 (3)	C2—Fe—C10—C9	−48.1 (7)
C3—C4—C5—Fe	59.1 (3)	C4—Fe—C10—C9	−117.5 (3)
C2—C1—C5—C4	0.5 (4)	C3—Fe—C10—C9	−77.2 (3)
C11—C1—C5—C4	179.6 (3)	C12—N1—C11—O1	161.1 (3)
Fe—C1—C5—C4	60.2 (3)	C18—N1—C11—O1	−8.8 (5)
C2—C1—C5—Fe	−59.7 (3)	C12—N1—C11—C1	−18.4 (5)
C11—C1—C5—Fe	119.4 (3)	C18—N1—C11—C1	171.7 (3)
C6—Fe—C5—C4	122.5 (3)	C2—C1—C11—O1	131.9 (4)
C1—Fe—C5—C4	−118.1 (3)	C5—C1—C11—O1	−47.0 (5)
C10—Fe—C5—C4	80.5 (3)	Fe—C1—C11—O1	40.6 (5)
C7—Fe—C5—C4	163.1 (3)	C2—C1—C11—N1	−48.6 (5)
C8—Fe—C5—C4	−167.0 (5)	C5—C1—C11—N1	132.5 (4)
C9—Fe—C5—C4	48.4 (5)	Fe—C1—C11—N1	−139.9 (3)
C2—Fe—C5—C4	−80.2 (3)	C11—N1—C12—C13	119.1 (4)
C3—Fe—C5—C4	−36.4 (3)	C18—N1—C12—C13	−70.5 (4)
C6—Fe—C5—C1	−119.5 (2)	C11—N1—C12—C17	−62.0 (4)
C10—Fe—C5—C1	−161.4 (2)	C18—N1—C12—C17	108.4 (4)
C7—Fe—C5—C1	−78.8 (3)	C17—C12—C13—C14	1.5 (6)
C8—Fe—C5—C1	−48.9 (7)	N1—C12—C13—C14	−179.7 (3)
C9—Fe—C5—C1	166.4 (4)	C12—C13—C14—C15	−0.3 (6)
C2—Fe—C5—C1	37.8 (2)	C13—C14—C15—C16	−0.8 (6)
C4—Fe—C5—C1	118.1 (3)	C14—C15—C16—C17	0.7 (7)
C3—Fe—C5—C1	81.7 (2)	C13—C12—C17—C16	−1.5 (6)
C1—Fe—C6—C10	−159.5 (3)	N1—C12—C17—C16	179.6 (3)
C5—Fe—C6—C10	−117.6 (3)	C15—C16—C17—C12	0.4 (6)
C7—Fe—C6—C10	116.7 (4)	C11—N1—C18—C23	−40.6 (5)
C8—Fe—C6—C10	80.3 (3)	C12—N1—C18—C23	149.2 (3)
C9—Fe—C6—C10	36.5 (3)	C11—N1—C18—C19	143.3 (4)
C2—Fe—C6—C10	170.6 (4)	C12—N1—C18—C19	−26.8 (5)
C4—Fe—C6—C10	−76.7 (3)	C23—C18—C19—C20	0.2 (6)
C3—Fe—C6—C10	−47.6 (6)	N1—C18—C19—C20	176.4 (4)
C1—Fe—C6—C7	83.8 (3)	C18—C19—C20—C21	1.1 (7)
C5—Fe—C6—C7	125.7 (3)	C19—C20—C21—C22	−1.4 (8)
C10—Fe—C6—C7	−116.7 (4)	C20—C21—C22—C23	0.3 (7)
C8—Fe—C6—C7	−36.5 (3)	C19—C18—C23—C22	−1.3 (6)
C9—Fe—C6—C7	−80.2 (3)	N1—C18—C23—C22	−177.3 (3)
C2—Fe—C6—C7	53.9 (5)	C21—C22—C23—C18	1.0 (6)
C4—Fe—C6—C7	166.5 (2)	C10—C6—C24—O2	159.6 (4)
C3—Fe—C6—C7	−164.3 (4)	C7—C6—C24—O2	−20.3 (7)
C1—Fe—C6—C24	−39.8 (5)	Fe—C6—C24—O2	70.7 (6)
C5—Fe—C6—C24	2.0 (4)	C10—C6—C24—C25	−78.7 (7)
C10—Fe—C6—C24	119.7 (5)	C7—C6—C24—C25	101.4 (6)
C7—Fe—C6—C24	−123.6 (5)	Fe—C6—C24—C25	−167.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	2.08	2.876 (5)	162
C19—H19···Cg2^i	0.93	3.25	3.933 (5)	132
C19—H19···C10^i	0.93	3.09	3.931 (6)	152
C19—H19···C6^i	0.93	3.36	4.005 (6)	129
C2—H2A···Cg3^ii	0.93	3.20	3.912 (4)	135
C2—H2A···C23^ii	0.93	2.93	3.777 (5)	152
C2—H2A···C18^ii	0.93	3.20	4.068 (5)	156

Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+2.