Two novel ferrocenyl dipeptide-like compounds generated via the Ugi four-component reaction

The Ugi four-component reaction, a powerful method for the synthesis of diverse dipeptide-like derivatives in combinatorial chemistry, was used to synthesize (S)-1′-{N-[1-(anthra­cen-9-yl)-2-(tert-butyl­amino)-2-oxo­ethyl]-N-(4-meth­oxyphenyl)carbamoyl}ferro­cene-1-carb­oxy­lic acid di­chloro­methane disolvate, [Fe(C₆H₅O₂)(C₃₃H₃₁N₂O₃)]·2CH₂Cl₂, (I), and (S)-2-(anthracen-9-yl)-N-tert-butyl-2-[N-(4-methyl­phenyl)ferrocenyl­formamido]­acetamide, [Fe(C₅H₅)(C₃₃H₃₁N₂O₂)], (II). They adopt broadly similar mol­ecular conformations, with near-eclipsed cyclo­penta­dienyl rings and near-perpendicular amide planes in their dipeptide-like chains, one of which is almost coplanar with its attached cyclo­penta­dienyl ring but perpendicular to the aromatic ring bound to the N atom. In the supra­molecular structure of (I), a two-dimensional network is constructed based on mol­ecular dimers and a combination of inter­molecular O—H...O, N—H...O and C—H...O hydrogen bonds, forming R₂²(11), R₂²(16), R₂²(22) and C(9) motifs. These two-dimensional networks are connected by C—H...O and C—H...Cl contacts to create a three-dimensional framework, where one di­chloro­methane solvent mol­ecule acts as a bridge between two neigh­bouring networks. In the packing of (II), classical hydrogen bonds are absent and an infinite one-dimensional chain is generated via a combination of C—H...O hydrogen bonds and C—H...π inter­actions, producing a C(7) motif. This work describes a simple synthesis and the supra­molecuar structures of ferrocenyl dipeptide-like compounds and is significant in the development of redox-active receptors.

Computing details

For both compounds, data collection: SMART (Bruker, 1999); cell refinement: SMART (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(I) (S)-1'-{N-[1-(Anthracen-9-yl)-2-(tert-butylamino)-2-oxoethyl]-N-(4-methoxyphenyl)carbamoyl}ferrocene-1-carboxylic acid dichloromethane disolvate

Crystal data

[Fe(C6H5O2)(C33H31N2O3)]·2(CH2Cl2)	F(000) = 1736
Mr = 838.40	Dx = 1.448 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
a = 14.1963 (8) Å	Cell parameters from 3184 reflections
b = 14.8203 (9) Å	θ = 3.6–25.8°
c = 18.7386 (9) Å	µ = 0.72 mm^−1
β = 102.663 (5)°	T = 100 K
V = 3846.6 (4) Å^3	Plate, clear light orange
Z = 4	0.17 × 0.15 × 0.04 mm

Data collection

Agilent SuperNova Dual diffractometer (Cu at zero) with Eos detector	7963 independent reflections
Radiation source: SuperNova (Mo) X-ray source	5178 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.062
Detector resolution: 16.0793 pixels mm^-1	θmax = 26.5°, θmin = 2.9°
ω scans	h = −17→17
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −18→12
Tmin = 0.994, Tmax = 1.000	l = −23→23
17873 measured 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0372P)^2 + 9.1089P] where P = (Fo^2 + 2Fc^2)/3
7963 reflections	(Δ/σ)max = 0.005
483 parameters	Δρmax = 0.94 e Å^−3
0 restraints	Δρmin = −1.03 e Å^−3

Special details

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C1	0.4787 (3)	0.6839 (3)	0.0293 (2)	0.0157 (9)
C2	0.4641 (3)	0.7174 (3)	0.1009 (2)	0.0150 (9)
C3	0.4019 (3)	0.7901 (3)	0.1101 (2)	0.0169 (9)
H3	0.3661	0.8261	0.0733	0.020*
C4	0.4049 (3)	0.7972 (3)	0.1864 (2)	0.0175 (10)
H4	0.3715	0.8392	0.2081	0.021*
C5	0.4675 (3)	0.7294 (3)	0.2238 (2)	0.0180 (10)
H5	0.4820	0.7195	0.2741	0.022*
C6	0.5041 (3)	0.6793 (3)	0.1714 (2)	0.0173 (9)
H6	0.5463	0.6306	0.1809	0.021*
C7	0.2853 (3)	0.5837 (3)	0.2011 (2)	0.0138 (9)
H7	0.3037	0.5674	0.2501	0.017*
C8	0.2230 (3)	0.6559 (3)	0.1721 (2)	0.0155 (9)
H8	0.1932	0.6951	0.1990	0.019*
C9	0.2136 (3)	0.6587 (3)	0.0951 (2)	0.0174 (10)
H9	0.1769	0.6998	0.0631	0.021*
C10	0.2701 (3)	0.5879 (3)	0.0755 (2)	0.0168 (10)
H10	0.2769	0.5747	0.0284	0.020*
C11	0.3150 (3)	0.5400 (3)	0.1408 (2)	0.0128 (9)
C12	0.3803 (3)	0.4625 (3)	0.1352 (2)	0.0125 (9)
C13	0.4230 (3)	0.4433 (3)	0.2689 (2)	0.0123 (9)
C14	0.4826 (3)	0.5085 (3)	0.3073 (2)	0.0166 (9)
H14	0.5328	0.5320	0.2884	0.020*
C15	0.4681 (3)	0.5395 (3)	0.3745 (2)	0.0205 (10)
H15	0.5067	0.5850	0.3997	0.025*
C16	0.3944 (3)	0.5009 (3)	0.4032 (2)	0.0181 (10)
C17	0.3385 (3)	0.4321 (3)	0.3664 (2)	0.0192 (10)
H17	0.2915	0.4051	0.3868	0.023*
C18	0.3520 (3)	0.4032 (3)	0.2991 (2)	0.0138 (9)
H18	0.3139	0.3572	0.2742	0.017*
C19	0.4091 (4)	0.6121 (3)	0.4979 (2)	0.0314 (13)
H19A	0.4783	0.6107	0.5119	0.047*
H19B	0.3832	0.6255	0.5399	0.047*
H19C	0.3893	0.6577	0.4613	0.047*
C20	0.4916 (3)	0.3428 (3)	0.1835 (2)	0.0135 (9)
H20	0.5084	0.3558	0.1366	0.016*
C21	0.5888 (3)	0.3379 (3)	0.2384 (2)	0.0143 (9)
C22	0.6049 (3)	0.2843 (3)	0.3023 (2)	0.0148 (9)
C23	0.5308 (3)	0.2362 (3)	0.3270 (2)	0.0185 (10)
H23	0.4676	0.2401	0.3001	0.022*
C24	0.5501 (3)	0.1846 (3)	0.3889 (2)	0.0203 (10)
H24	0.4999	0.1549	0.4037	0.024*
C25	0.6453 (3)	0.1758 (3)	0.4308 (2)	0.0219 (10)
H25	0.6577	0.1391	0.4720	0.026*
C26	0.7184 (3)	0.2207 (3)	0.4109 (2)	0.0204 (10)
H26	0.7806	0.2151	0.4393	0.024*
C27	0.7018 (3)	0.2769 (3)	0.3468 (2)	0.0171 (10)
C28	0.7780 (3)	0.3229 (3)	0.3267 (2)	0.0200 (10)
H28	0.8403	0.3160	0.3547	0.024*
C29	0.7620 (3)	0.3795 (3)	0.2650 (2)	0.0179 (10)
C30	0.8393 (3)	0.4266 (3)	0.2451 (2)	0.0236 (11)
H30	0.9018	0.4181	0.2723	0.028*
C31	0.8241 (3)	0.4839 (3)	0.1868 (2)	0.0255 (11)
H31	0.8756	0.5150	0.1752	0.031*
C32	0.7291 (3)	0.4958 (3)	0.1440 (2)	0.0237 (11)
H32	0.7185	0.5354	0.1046	0.028*
C33	0.6535 (3)	0.4499 (3)	0.1602 (2)	0.0176 (10)
H33	0.5921	0.4585	0.1312	0.021*
C34	0.6654 (3)	0.3881 (3)	0.2210 (2)	0.0158 (9)
C35	0.4322 (3)	0.2541 (3)	0.1701 (2)	0.0136 (9)
C36	0.4397 (3)	0.0988 (3)	0.1174 (2)	0.0193 (10)
C37	0.5217 (3)	0.0482 (3)	0.0942 (2)	0.0248 (11)
H37A	0.5396	0.0796	0.0544	0.037*
H37B	0.5007	−0.0117	0.0789	0.037*
H37C	0.5763	0.0450	0.1347	0.037*
C38	0.4098 (4)	0.0495 (3)	0.1805 (3)	0.0299 (12)
H38A	0.4633	0.0478	0.2219	0.045*
H38B	0.3907	−0.0110	0.1657	0.045*
H38C	0.3567	0.0806	0.1935	0.045*
C39	0.3548 (4)	0.1103 (4)	0.0522 (3)	0.0383 (14)
H39A	0.3055	0.1458	0.0665	0.057*
H39B	0.3292	0.0520	0.0359	0.057*
H39C	0.3763	0.1401	0.0132	0.057*
C40	0.7245 (4)	0.7209 (4)	0.3771 (3)	0.0391 (14)
H40A	0.6738	0.7642	0.3587	0.047*
H40B	0.7837	0.7540	0.3959	0.047*
C41	0.4305 (4)	0.9371 (4)	0.3813 (3)	0.0451 (16)
H41A	0.4031	0.9889	0.4011	0.054*
H41B	0.4461	0.9553	0.3355	0.054*
Cl1	0.74051 (10)	0.64963 (10)	0.30513 (6)	0.0363 (3)
Cl2	0.69365 (11)	0.65685 (13)	0.44833 (7)	0.0542 (5)
Cl3	0.34442 (9)	0.85026 (10)	0.36429 (6)	0.0336 (3)
Cl4	0.53763 (11)	0.90397 (15)	0.44327 (8)	0.0668 (6)
Fe1	0.35616 (4)	0.67244 (4)	0.14741 (3)	0.01285 (16)
N1	0.4314 (2)	0.4194 (2)	0.19572 (17)	0.0127 (8)
N2	0.4786 (3)	0.1885 (3)	0.14253 (18)	0.0171 (8)
H2	0.5369	0.1998	0.1391	0.021*
O1	0.4376 (2)	0.7151 (2)	−0.02928 (14)	0.0203 (7)
O2	0.5428 (2)	0.6180 (2)	0.03756 (15)	0.0225 (8)
H2A	0.5563	0.6068	−0.0019	0.034*
O3	0.3869 (2)	0.4386 (2)	0.07295 (14)	0.0190 (7)
O4	0.3741 (2)	0.5257 (2)	0.46875 (15)	0.0259 (8)
O5	0.3497 (2)	0.2484 (2)	0.18046 (15)	0.0201 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.014 (2)	0.014 (2)	0.023 (2)	−0.0043 (19)	0.0127 (17)	0.0003 (19)
C2	0.015 (2)	0.015 (2)	0.015 (2)	−0.0008 (19)	0.0026 (16)	0.0007 (18)
C3	0.022 (2)	0.009 (2)	0.020 (2)	0.0005 (19)	0.0068 (18)	0.0002 (18)
C4	0.021 (2)	0.010 (2)	0.025 (2)	−0.0032 (19)	0.0129 (18)	−0.0052 (19)
C5	0.017 (2)	0.021 (3)	0.016 (2)	−0.008 (2)	0.0041 (17)	−0.0044 (19)
C6	0.013 (2)	0.017 (2)	0.023 (2)	−0.003 (2)	0.0044 (17)	−0.0012 (19)
C7	0.014 (2)	0.012 (2)	0.0167 (19)	−0.0051 (19)	0.0067 (16)	0.0025 (18)
C8	0.015 (2)	0.012 (2)	0.021 (2)	0.0022 (19)	0.0073 (17)	−0.0006 (19)
C9	0.010 (2)	0.018 (3)	0.023 (2)	−0.0011 (19)	0.0022 (17)	0.001 (2)
C10	0.012 (2)	0.021 (3)	0.017 (2)	−0.001 (2)	0.0011 (16)	−0.0003 (19)
C11	0.014 (2)	0.008 (2)	0.0162 (19)	−0.0013 (18)	0.0035 (16)	−0.0011 (17)
C12	0.013 (2)	0.006 (2)	0.020 (2)	−0.0011 (18)	0.0050 (16)	0.0010 (18)
C13	0.013 (2)	0.011 (2)	0.0117 (18)	0.0033 (18)	−0.0007 (16)	−0.0008 (17)
C14	0.015 (2)	0.018 (3)	0.018 (2)	0.0040 (19)	0.0063 (17)	0.0030 (19)
C15	0.020 (2)	0.020 (3)	0.019 (2)	0.000 (2)	−0.0021 (18)	−0.002 (2)
C16	0.023 (2)	0.016 (2)	0.016 (2)	0.006 (2)	0.0047 (17)	0.0001 (19)
C17	0.018 (2)	0.018 (3)	0.021 (2)	0.000 (2)	0.0054 (18)	0.006 (2)
C18	0.013 (2)	0.011 (2)	0.017 (2)	0.0009 (18)	0.0025 (16)	0.0039 (18)
C19	0.040 (3)	0.028 (3)	0.024 (2)	0.012 (3)	0.001 (2)	−0.004 (2)
C20	0.015 (2)	0.011 (2)	0.0149 (19)	0.0021 (18)	0.0051 (16)	0.0005 (17)
C21	0.013 (2)	0.012 (2)	0.019 (2)	0.0022 (18)	0.0047 (16)	−0.0004 (18)
C22	0.016 (2)	0.010 (2)	0.018 (2)	0.0014 (19)	0.0047 (17)	−0.0049 (18)
C23	0.017 (2)	0.021 (3)	0.017 (2)	0.004 (2)	0.0049 (17)	0.0023 (19)
C24	0.026 (2)	0.018 (3)	0.020 (2)	0.000 (2)	0.0125 (18)	−0.002 (2)
C25	0.035 (3)	0.017 (3)	0.017 (2)	0.007 (2)	0.0103 (19)	0.0010 (19)
C26	0.025 (3)	0.016 (3)	0.015 (2)	0.005 (2)	−0.0056 (18)	−0.0033 (19)
C27	0.018 (2)	0.013 (2)	0.020 (2)	0.0044 (19)	0.0038 (17)	−0.0086 (19)
C28	0.021 (2)	0.016 (2)	0.020 (2)	0.003 (2)	−0.0011 (18)	−0.007 (2)
C29	0.014 (2)	0.017 (2)	0.023 (2)	−0.003 (2)	0.0031 (17)	−0.0085 (19)
C30	0.016 (2)	0.024 (3)	0.031 (2)	−0.003 (2)	0.0036 (19)	−0.007 (2)
C31	0.024 (3)	0.020 (3)	0.036 (3)	−0.008 (2)	0.013 (2)	−0.001 (2)
C32	0.028 (3)	0.018 (3)	0.026 (2)	−0.003 (2)	0.008 (2)	0.005 (2)
C33	0.014 (2)	0.015 (2)	0.022 (2)	0.0011 (19)	0.0019 (17)	0.0012 (19)
C34	0.018 (2)	0.009 (2)	0.020 (2)	0.0012 (19)	0.0055 (17)	0.0009 (18)
C35	0.015 (2)	0.013 (2)	0.0119 (19)	0.0012 (19)	0.0003 (16)	−0.0002 (17)
C36	0.022 (2)	0.013 (2)	0.024 (2)	−0.003 (2)	0.0061 (18)	−0.005 (2)
C37	0.032 (3)	0.016 (3)	0.028 (2)	−0.003 (2)	0.009 (2)	−0.007 (2)
C38	0.036 (3)	0.015 (3)	0.045 (3)	0.000 (2)	0.022 (2)	0.000 (2)
C39	0.035 (3)	0.034 (3)	0.039 (3)	0.005 (3)	−0.007 (2)	−0.007 (3)
C40	0.035 (3)	0.047 (4)	0.036 (3)	−0.008 (3)	0.008 (2)	−0.005 (3)
C41	0.037 (3)	0.049 (4)	0.045 (3)	0.001 (3)	0.000 (3)	0.017 (3)
Cl1	0.0377 (7)	0.0409 (9)	0.0305 (6)	0.0026 (7)	0.0077 (5)	0.0073 (6)
Cl2	0.0485 (9)	0.0864 (14)	0.0283 (7)	−0.0343 (9)	0.0096 (6)	−0.0030 (8)
Cl3	0.0381 (7)	0.0389 (8)	0.0243 (6)	−0.0006 (6)	0.0079 (5)	0.0004 (6)
Cl4	0.0317 (8)	0.1232 (18)	0.0421 (8)	−0.0020 (10)	0.0006 (6)	0.0283 (10)
Fe1	0.0140 (3)	0.0115 (3)	0.0138 (3)	0.0013 (3)	0.0048 (2)	0.0000 (3)
N1	0.0118 (17)	0.013 (2)	0.0137 (16)	0.0011 (16)	0.0045 (13)	0.0005 (15)
N2	0.0144 (19)	0.016 (2)	0.0220 (18)	−0.0020 (16)	0.0058 (14)	−0.0026 (16)
O1	0.0233 (17)	0.0225 (19)	0.0158 (15)	0.0034 (15)	0.0062 (12)	0.0037 (14)
O2	0.0218 (17)	0.032 (2)	0.0155 (14)	0.0128 (16)	0.0080 (13)	−0.0007 (14)
O3	0.0211 (16)	0.0204 (18)	0.0157 (14)	0.0061 (14)	0.0044 (12)	−0.0035 (13)
O4	0.037 (2)	0.025 (2)	0.0171 (15)	0.0045 (17)	0.0097 (14)	−0.0032 (14)
O5	0.0159 (16)	0.0160 (18)	0.0287 (16)	0.0002 (14)	0.0052 (13)	−0.0017 (14)

Geometric parameters (Å, º)

C1—O1	1.215 (5)	C20—C35	1.552 (6)
C1—O2	1.322 (5)	C20—H20	0.9800
C1—C2	1.488 (5)	C21—C34	1.414 (6)
C2—C3	1.427 (6)	C21—C22	1.414 (6)
C2—C6	1.435 (6)	C22—C23	1.428 (6)
C2—Fe1	2.034 (4)	C22—C27	1.448 (6)
C3—C4	1.424 (5)	C23—C24	1.366 (6)
C3—Fe1	2.037 (4)	C23—H23	0.9300
C3—H3	0.9300	C24—C25	1.412 (6)
C4—C5	1.421 (6)	C24—H24	0.9300
C4—Fe1	2.051 (4)	C25—C26	1.351 (6)
C4—H4	0.9300	C25—H25	0.9300
C5—C6	1.418 (6)	C26—C27	1.439 (6)
C5—Fe1	2.066 (4)	C26—H26	0.9300
C5—H5	0.9300	C27—C28	1.398 (6)
C6—Fe1	2.051 (4)	C28—C29	1.406 (6)
C6—H6	0.9300	C28—H28	0.9300
C7—C8	1.419 (6)	C29—C30	1.419 (6)
C7—C11	1.444 (6)	C29—C34	1.442 (6)
C7—Fe1	2.049 (4)	C30—C31	1.362 (6)
C7—H7	0.9300	C30—H30	0.9300
C8—C9	1.419 (6)	C31—C32	1.421 (6)
C8—Fe1	2.057 (4)	C31—H31	0.9300
C8—H8	0.9300	C32—C33	1.360 (6)
C9—C10	1.416 (6)	C32—H32	0.9300
C9—Fe1	2.056 (4)	C33—C34	1.441 (6)
C9—H9	0.9300	C33—H33	0.9300
C10—C11	1.437 (6)	C35—O5	1.232 (5)
C10—Fe1	2.038 (4)	C35—N2	1.338 (5)
C10—H10	0.9300	C36—N2	1.476 (5)
C11—C12	1.493 (6)	C36—C39	1.526 (6)
C11—Fe1	2.044 (4)	C36—C37	1.526 (6)
C12—O3	1.242 (5)	C36—C38	1.526 (6)
C12—N1	1.364 (5)	C37—H37A	0.9600
C13—C14	1.379 (6)	C37—H37B	0.9600
C13—C18	1.393 (6)	C37—H37C	0.9600
C13—N1	1.446 (5)	C38—H38A	0.9600
C14—C15	1.397 (6)	C38—H38B	0.9600
C14—H14	0.9300	C38—H38C	0.9600
C15—C16	1.398 (6)	C39—H39A	0.9600
C15—H15	0.9300	C39—H39B	0.9600
C16—O4	1.373 (5)	C39—H39C	0.9600
C16—C17	1.380 (6)	C40—Cl1	1.766 (5)
C17—C18	1.384 (6)	C40—Cl2	1.769 (5)
C17—H17	0.9300	C40—H40A	0.9700
C18—H18	0.9300	C40—H40B	0.9700
C19—O4	1.437 (6)	C41—Cl3	1.755 (6)
C19—H19A	0.9600	C41—Cl4	1.768 (5)
C19—H19B	0.9600	C41—H41A	0.9700
C19—H19C	0.9600	C41—H41B	0.9700
C20—N1	1.469 (5)	N2—H2	0.8600
C20—C21	1.531 (5)	O2—H2A	0.8200
O1—C1—O2	124.7 (4)	C28—C27—C22	120.2 (4)
O1—C1—C2	123.6 (4)	C26—C27—C22	119.0 (4)
O2—C1—C2	111.7 (4)	C27—C28—C29	121.1 (4)
C3—C2—C6	108.4 (4)	C27—C28—H28	119.5
C3—C2—C1	125.0 (4)	C29—C28—H28	119.5
C6—C2—C1	126.4 (4)	C28—C29—C30	121.0 (4)
C3—C2—Fe1	69.6 (2)	C28—C29—C34	119.0 (4)
C6—C2—Fe1	70.1 (2)	C30—C29—C34	120.0 (4)
C1—C2—Fe1	122.9 (3)	C31—C30—C29	121.4 (4)
C4—C3—C2	107.1 (4)	C31—C30—H30	119.3
C4—C3—Fe1	70.1 (2)	C29—C30—H30	119.3
C2—C3—Fe1	69.4 (2)	C30—C31—C32	119.7 (4)
C4—C3—H3	126.5	C30—C31—H31	120.2
C2—C3—H3	126.5	C32—C31—H31	120.2
Fe1—C3—H3	125.6	C33—C32—C31	120.6 (4)
C5—C4—C3	108.8 (4)	C33—C32—H32	119.7
C5—C4—Fe1	70.4 (2)	C31—C32—H32	119.7
C3—C4—Fe1	69.1 (2)	C32—C33—C34	122.2 (4)
C5—C4—H4	125.6	C32—C33—H33	118.9
C3—C4—H4	125.6	C34—C33—H33	118.9
Fe1—C4—H4	126.5	C21—C34—C33	123.6 (4)
C6—C5—C4	108.2 (4)	C21—C34—C29	120.3 (4)
C6—C5—Fe1	69.3 (2)	C33—C34—C29	116.1 (4)
C4—C5—Fe1	69.3 (2)	O5—C35—N2	125.2 (4)
C6—C5—H5	125.9	O5—C35—C20	122.3 (4)
C4—C5—H5	125.9	N2—C35—C20	112.4 (4)
Fe1—C5—H5	127.1	N2—C36—C39	109.3 (4)
C5—C6—C2	107.5 (4)	N2—C36—C37	106.1 (4)
C5—C6—Fe1	70.4 (2)	C39—C36—C37	110.1 (4)
C2—C6—Fe1	68.8 (2)	N2—C36—C38	109.5 (3)
C5—C6—H6	126.2	C39—C36—C38	111.6 (4)
C2—C6—H6	126.2	C37—C36—C38	110.1 (4)
Fe1—C6—H6	126.1	C36—C37—H37A	109.5
C8—C7—C11	107.6 (3)	C36—C37—H37B	109.5
C8—C7—Fe1	70.1 (2)	H37A—C37—H37B	109.5
C11—C7—Fe1	69.2 (2)	C36—C37—H37C	109.5
C8—C7—H7	126.2	H37A—C37—H37C	109.5
C11—C7—H7	126.2	H37B—C37—H37C	109.5
Fe1—C7—H7	126.2	C36—C38—H38A	109.5
C9—C8—C7	108.9 (4)	C36—C38—H38B	109.5
C9—C8—Fe1	69.8 (2)	H38A—C38—H38B	109.5
C7—C8—Fe1	69.5 (2)	C36—C38—H38C	109.5
C9—C8—H8	125.6	H38A—C38—H38C	109.5
C7—C8—H8	125.6	H38B—C38—H38C	109.5
Fe1—C8—H8	126.8	C36—C39—H39A	109.5
C10—C9—C8	108.0 (4)	C36—C39—H39B	109.5
C10—C9—Fe1	69.1 (2)	H39A—C39—H39B	109.5
C8—C9—Fe1	69.8 (2)	C36—C39—H39C	109.5
C10—C9—H9	126.0	H39A—C39—H39C	109.5
C8—C9—H9	126.0	H39B—C39—H39C	109.5
Fe1—C9—H9	126.6	Cl1—C40—Cl2	110.5 (3)
C9—C10—C11	108.5 (4)	Cl1—C40—H40A	109.5
C9—C10—Fe1	70.4 (2)	Cl2—C40—H40A	109.5
C11—C10—Fe1	69.6 (2)	Cl1—C40—H40B	109.6
C9—C10—H10	125.8	Cl2—C40—H40B	109.6
C11—C10—H10	125.8	H40A—C40—H40B	108.1
Fe1—C10—H10	125.8	Cl3—C41—Cl4	112.3 (3)
C10—C11—C7	107.0 (4)	Cl3—C41—H41A	109.1
C10—C11—C12	119.1 (4)	Cl4—C41—H41A	109.1
C7—C11—C12	133.8 (4)	Cl3—C41—H41B	109.1
C10—C11—Fe1	69.2 (2)	Cl4—C41—H41B	109.1
C7—C11—Fe1	69.5 (2)	H41A—C41—H41B	107.9
C12—C11—Fe1	124.7 (3)	C3—Fe1—C2	41.03 (17)
O3—C12—N1	120.7 (4)	C3—Fe1—C10	119.29 (17)
O3—C12—C11	117.5 (3)	C2—Fe1—C10	108.48 (16)
N1—C12—C11	121.8 (3)	C3—Fe1—C11	155.44 (16)
C14—C13—C18	120.1 (4)	C2—Fe1—C11	121.38 (17)
C14—C13—N1	119.9 (4)	C10—Fe1—C11	41.22 (16)
C18—C13—N1	119.9 (4)	C3—Fe1—C7	161.03 (17)
C13—C14—C15	120.4 (4)	C2—Fe1—C7	156.63 (17)
C13—C14—H14	119.8	C10—Fe1—C7	69.04 (16)
C15—C14—H14	119.8	C11—Fe1—C7	41.32 (16)
C14—C15—C16	118.9 (4)	C3—Fe1—C6	69.20 (18)
C14—C15—H15	120.6	C2—Fe1—C6	41.11 (16)
C16—C15—H15	120.6	C10—Fe1—C6	127.71 (17)
O4—C16—C17	115.7 (4)	C11—Fe1—C6	109.01 (18)
O4—C16—C15	123.8 (4)	C7—Fe1—C6	120.89 (17)
C17—C16—C15	120.4 (4)	C3—Fe1—C4	40.75 (16)
C16—C17—C18	120.3 (4)	C2—Fe1—C4	68.27 (17)
C16—C17—H17	119.8	C10—Fe1—C4	153.58 (17)
C18—C17—H17	119.8	C11—Fe1—C4	163.09 (16)
C17—C18—C13	119.7 (4)	C7—Fe1—C4	124.59 (16)
C17—C18—H18	120.2	C6—Fe1—C4	68.16 (18)
C13—C18—H18	120.2	C3—Fe1—C9	105.98 (18)
O4—C19—H19A	109.5	C2—Fe1—C9	125.66 (16)
O4—C19—H19B	109.5	C10—Fe1—C9	40.48 (17)
H19A—C19—H19B	109.5	C11—Fe1—C9	68.78 (17)
O4—C19—H19C	109.5	C7—Fe1—C9	68.47 (17)
H19A—C19—H19C	109.5	C6—Fe1—C9	164.26 (16)
H19B—C19—H19C	109.5	C4—Fe1—C9	118.61 (18)
N1—C20—C21	113.7 (3)	C3—Fe1—C8	123.82 (17)
N1—C20—C35	111.5 (3)	C2—Fe1—C8	161.99 (16)
C21—C20—C35	116.5 (3)	C10—Fe1—C8	68.15 (17)
N1—C20—H20	104.6	C11—Fe1—C8	68.61 (17)
C21—C20—H20	104.6	C7—Fe1—C8	40.45 (16)
C35—C20—H20	104.6	C6—Fe1—C8	154.69 (16)
C34—C21—C22	120.1 (4)	C4—Fe1—C8	106.41 (17)
C34—C21—C20	116.5 (3)	C9—Fe1—C8	40.39 (16)
C22—C21—C20	123.4 (4)	C3—Fe1—C5	68.61 (17)
C21—C22—C23	124.1 (4)	C2—Fe1—C5	68.26 (16)
C21—C22—C27	119.1 (4)	C10—Fe1—C5	164.95 (18)
C23—C22—C27	116.8 (4)	C11—Fe1—C5	126.81 (17)
C24—C23—C22	122.0 (4)	C7—Fe1—C5	107.76 (16)
C24—C23—H23	119.0	C6—Fe1—C5	40.29 (16)
C22—C23—H23	119.0	C4—Fe1—C5	40.37 (17)
C23—C24—C25	120.8 (4)	C9—Fe1—C5	153.42 (18)
C23—C24—H24	119.6	C8—Fe1—C5	119.61 (16)
C25—C24—H24	119.6	C12—N1—C13	122.3 (3)
C26—C25—C24	120.1 (4)	C12—N1—C20	117.0 (3)
C26—C25—H25	120.0	C13—N1—C20	120.6 (3)
C24—C25—H25	120.0	C35—N2—C36	126.5 (4)
C25—C26—C27	121.3 (4)	C35—N2—H2	116.8
C25—C26—H26	119.3	C36—N2—H2	116.8
C27—C26—H26	119.3	C1—O2—H2A	109.5
C28—C27—C26	120.8 (4)	C16—O4—C19	117.1 (4)
O1—C1—C2—C3	−0.7 (7)	C9—C10—Fe1—C6	−165.5 (2)
O2—C1—C2—C3	177.9 (4)	C11—C10—Fe1—C6	75.1 (3)
O1—C1—C2—C6	174.7 (4)	C9—C10—Fe1—C4	−45.5 (5)
O2—C1—C2—C6	−6.7 (6)	C11—C10—Fe1—C4	−165.0 (3)
O1—C1—C2—Fe1	86.2 (5)	C11—C10—Fe1—C9	−119.4 (3)
O2—C1—C2—Fe1	−95.2 (4)	C9—C10—Fe1—C8	37.4 (2)
C6—C2—C3—C4	0.8 (5)	C11—C10—Fe1—C8	−82.0 (3)
C1—C2—C3—C4	176.9 (4)	C9—C10—Fe1—C5	161.4 (6)
Fe1—C2—C3—C4	60.3 (3)	C11—C10—Fe1—C5	42.0 (7)
C6—C2—C3—Fe1	−59.5 (3)	C10—C11—Fe1—C3	−44.7 (5)
C1—C2—C3—Fe1	116.6 (4)	C7—C11—Fe1—C3	−163.1 (4)
C2—C3—C4—C5	−0.5 (5)	C12—C11—Fe1—C3	67.1 (5)
Fe1—C3—C4—C5	59.3 (3)	C10—C11—Fe1—C2	−82.4 (3)
C2—C3—C4—Fe1	−59.8 (3)	C7—C11—Fe1—C2	159.2 (2)
C3—C4—C5—C6	0.0 (5)	C12—C11—Fe1—C2	29.4 (4)
Fe1—C4—C5—C6	58.5 (3)	C7—C11—Fe1—C10	−118.4 (3)
C3—C4—C5—Fe1	−58.6 (3)	C12—C11—Fe1—C10	111.7 (4)
C4—C5—C6—C2	0.5 (5)	C10—C11—Fe1—C7	118.4 (3)
Fe1—C5—C6—C2	59.0 (3)	C12—C11—Fe1—C7	−129.8 (4)
C4—C5—C6—Fe1	−58.5 (3)	C10—C11—Fe1—C6	−126.0 (2)
C3—C2—C6—C5	−0.8 (5)	C7—C11—Fe1—C6	115.5 (2)
C1—C2—C6—C5	−176.9 (4)	C12—C11—Fe1—C6	−14.3 (4)
Fe1—C2—C6—C5	−60.0 (3)	C10—C11—Fe1—C4	156.6 (5)
C3—C2—C6—Fe1	59.2 (3)	C7—C11—Fe1—C4	38.2 (7)
C1—C2—C6—Fe1	−116.8 (4)	C12—C11—Fe1—C4	−91.6 (7)
C11—C7—C8—C9	−0.4 (5)	C10—C11—Fe1—C9	37.3 (2)
Fe1—C7—C8—C9	58.8 (3)	C7—C11—Fe1—C9	−81.1 (3)
C11—C7—C8—Fe1	−59.2 (3)	C12—C11—Fe1—C9	149.1 (4)
C7—C8—C9—C10	0.1 (5)	C10—C11—Fe1—C8	80.8 (3)
Fe1—C8—C9—C10	58.7 (3)	C7—C11—Fe1—C8	−37.6 (2)
C7—C8—C9—Fe1	−58.6 (3)	C12—C11—Fe1—C8	−167.4 (4)
C8—C9—C10—C11	0.2 (5)	C10—C11—Fe1—C5	−167.5 (2)
Fe1—C9—C10—C11	59.4 (3)	C7—C11—Fe1—C5	74.1 (3)
C8—C9—C10—Fe1	−59.2 (3)	C12—C11—Fe1—C5	−55.7 (4)
C9—C10—C11—C7	−0.5 (5)	C8—C7—Fe1—C3	39.3 (6)
Fe1—C10—C11—C7	59.5 (3)	C11—C7—Fe1—C3	158.2 (5)
C9—C10—C11—C12	−179.0 (4)	C8—C7—Fe1—C2	−168.7 (4)
Fe1—C10—C11—C12	−119.0 (4)	C11—C7—Fe1—C2	−49.9 (5)
C9—C10—C11—Fe1	−59.9 (3)	C8—C7—Fe1—C10	−80.5 (3)
C8—C7—C11—C10	0.5 (5)	C11—C7—Fe1—C10	38.4 (2)
Fe1—C7—C11—C10	−59.2 (3)	C8—C7—Fe1—C11	−118.9 (3)
C8—C7—C11—C12	178.7 (4)	C8—C7—Fe1—C6	157.2 (2)
Fe1—C7—C11—C12	118.9 (5)	C11—C7—Fe1—C6	−83.9 (3)
C8—C7—C11—Fe1	59.8 (3)	C8—C7—Fe1—C4	73.8 (3)
C10—C11—C12—O3	−5.5 (6)	C11—C7—Fe1—C4	−167.4 (2)
C7—C11—C12—O3	176.5 (4)	C8—C7—Fe1—C9	−36.9 (2)
Fe1—C11—C12—O3	−89.2 (4)	C11—C7—Fe1—C9	81.9 (2)
C10—C11—C12—N1	174.3 (4)	C11—C7—Fe1—C8	118.9 (3)
C7—C11—C12—N1	−3.7 (7)	C8—C7—Fe1—C5	115.1 (3)
Fe1—C11—C12—N1	90.6 (4)	C11—C7—Fe1—C5	−126.1 (2)
C18—C13—C14—C15	−4.5 (6)	C5—C6—Fe1—C3	81.1 (3)
N1—C13—C14—C15	172.7 (4)	C2—C6—Fe1—C3	−37.6 (2)
C13—C14—C15—C16	2.4 (6)	C5—C6—Fe1—C2	118.7 (4)
C14—C15—C16—O4	179.7 (4)	C5—C6—Fe1—C10	−167.3 (3)
C14—C15—C16—C17	1.3 (6)	C2—C6—Fe1—C10	73.9 (3)
O4—C16—C17—C18	178.8 (4)	C5—C6—Fe1—C11	−125.0 (3)
C15—C16—C17—C18	−2.7 (6)	C2—C6—Fe1—C11	116.3 (3)
C16—C17—C18—C13	0.5 (6)	C5—C6—Fe1—C7	−81.0 (3)
C14—C13—C18—C17	3.1 (6)	C2—C6—Fe1—C7	160.3 (2)
N1—C13—C18—C17	−174.2 (4)	C5—C6—Fe1—C4	37.2 (3)
N1—C20—C21—C34	−86.7 (4)	C2—C6—Fe1—C4	−81.5 (3)
C35—C20—C21—C34	141.6 (4)	C5—C6—Fe1—C9	155.9 (6)
N1—C20—C21—C22	95.5 (5)	C2—C6—Fe1—C9	37.2 (8)
C35—C20—C21—C22	−36.3 (6)	C5—C6—Fe1—C8	−45.0 (5)
C34—C21—C22—C23	175.6 (4)	C2—C6—Fe1—C8	−163.7 (4)
C20—C21—C22—C23	−6.7 (7)	C2—C6—Fe1—C5	−118.7 (4)
C34—C21—C22—C27	−4.1 (6)	C5—C4—Fe1—C3	−120.2 (4)
C20—C21—C22—C27	173.6 (4)	C5—C4—Fe1—C2	−81.6 (3)
C21—C22—C23—C24	179.4 (4)	C3—C4—Fe1—C2	38.6 (2)
C27—C22—C23—C24	−0.9 (6)	C5—C4—Fe1—C10	−169.5 (3)
C22—C23—C24—C25	−0.9 (7)	C3—C4—Fe1—C10	−49.4 (5)
C23—C24—C25—C26	1.9 (7)	C5—C4—Fe1—C11	46.5 (7)
C24—C25—C26—C27	−1.0 (7)	C3—C4—Fe1—C11	166.6 (5)
C25—C26—C27—C28	−179.9 (4)	C5—C4—Fe1—C7	76.2 (3)
C25—C26—C27—C22	−0.8 (6)	C3—C4—Fe1—C7	−163.6 (2)
C21—C22—C27—C28	0.5 (6)	C5—C4—Fe1—C6	−37.1 (2)
C23—C22—C27—C28	−179.2 (4)	C3—C4—Fe1—C6	83.0 (3)
C21—C22—C27—C26	−178.6 (4)	C5—C4—Fe1—C9	158.6 (2)
C23—C22—C27—C26	1.7 (6)	C3—C4—Fe1—C9	−81.2 (3)
C26—C27—C28—C29	−178.6 (4)	C5—C4—Fe1—C8	116.7 (2)
C22—C27—C28—C29	2.3 (6)	C3—C4—Fe1—C8	−123.2 (3)
C27—C28—C29—C30	179.6 (4)	C3—C4—Fe1—C5	120.2 (4)
C27—C28—C29—C34	−1.5 (6)	C10—C9—Fe1—C3	116.6 (3)
C28—C29—C30—C31	−177.8 (4)	C8—C9—Fe1—C3	−123.8 (3)
C34—C29—C30—C31	3.3 (7)	C10—C9—Fe1—C2	76.1 (3)
C29—C30—C31—C32	−1.2 (7)	C8—C9—Fe1—C2	−164.4 (3)
C30—C31—C32—C33	−0.7 (7)	C8—C9—Fe1—C10	119.5 (4)
C31—C32—C33—C34	0.5 (7)	C10—C9—Fe1—C11	−38.0 (2)
C22—C21—C34—C33	−174.9 (4)	C8—C9—Fe1—C11	81.5 (3)
C20—C21—C34—C33	7.2 (6)	C10—C9—Fe1—C7	−82.5 (3)
C22—C21—C34—C29	5.0 (6)	C8—C9—Fe1—C7	37.0 (2)
C20—C21—C34—C29	−172.9 (4)	C10—C9—Fe1—C6	46.9 (8)
C32—C33—C34—C21	−178.6 (4)	C8—C9—Fe1—C6	166.4 (6)
C32—C33—C34—C29	1.6 (6)	C10—C9—Fe1—C4	158.8 (2)
C28—C29—C34—C21	−2.2 (6)	C8—C9—Fe1—C4	−81.7 (3)
C30—C29—C34—C21	176.8 (4)	C10—C9—Fe1—C8	−119.5 (4)
C28—C29—C34—C33	177.7 (4)	C10—C9—Fe1—C5	−169.3 (4)
C30—C29—C34—C33	−3.4 (6)	C8—C9—Fe1—C5	−49.8 (5)
N1—C20—C35—O5	−10.8 (5)	C9—C8—Fe1—C3	74.0 (3)
C21—C20—C35—O5	121.9 (4)	C7—C8—Fe1—C3	−165.6 (2)
N1—C20—C35—N2	165.6 (3)	C9—C8—Fe1—C2	45.1 (6)
C21—C20—C35—N2	−61.6 (5)	C7—C8—Fe1—C2	165.5 (5)
C4—C3—Fe1—C2	−118.0 (3)	C9—C8—Fe1—C10	−37.5 (3)
C4—C3—Fe1—C10	157.2 (3)	C7—C8—Fe1—C10	82.9 (3)
C2—C3—Fe1—C10	−84.8 (3)	C9—C8—Fe1—C11	−82.0 (3)
C4—C3—Fe1—C11	−170.7 (4)	C7—C8—Fe1—C11	38.4 (2)
C2—C3—Fe1—C11	−52.7 (5)	C9—C8—Fe1—C7	−120.4 (4)
C4—C3—Fe1—C7	45.5 (6)	C9—C8—Fe1—C6	−171.4 (4)
C2—C3—Fe1—C7	163.5 (4)	C7—C8—Fe1—C6	−51.0 (5)
C4—C3—Fe1—C6	−80.3 (3)	C9—C8—Fe1—C4	115.1 (3)
C2—C3—Fe1—C6	37.7 (2)	C7—C8—Fe1—C4	−124.5 (2)
C2—C3—Fe1—C4	118.0 (3)	C7—C8—Fe1—C9	120.4 (4)
C4—C3—Fe1—C9	115.5 (3)	C9—C8—Fe1—C5	156.8 (3)
C2—C3—Fe1—C9	−126.5 (2)	C7—C8—Fe1—C5	−82.8 (3)
C4—C3—Fe1—C8	75.1 (3)	C6—C5—Fe1—C3	−82.7 (3)
C2—C3—Fe1—C8	−166.9 (2)	C4—C5—Fe1—C3	37.3 (2)
C4—C3—Fe1—C5	−37.0 (3)	C6—C5—Fe1—C2	−38.4 (3)
C2—C3—Fe1—C5	81.0 (3)	C4—C5—Fe1—C2	81.6 (3)
C6—C2—Fe1—C3	119.6 (4)	C6—C5—Fe1—C10	41.9 (8)
C1—C2—Fe1—C3	−119.2 (4)	C4—C5—Fe1—C10	161.9 (6)
C3—C2—Fe1—C10	113.7 (2)	C6—C5—Fe1—C11	75.3 (3)
C6—C2—Fe1—C10	−126.7 (3)	C4—C5—Fe1—C11	−164.7 (2)
C1—C2—Fe1—C10	−5.5 (4)	C6—C5—Fe1—C7	117.1 (3)
C3—C2—Fe1—C11	157.2 (2)	C4—C5—Fe1—C7	−122.9 (2)
C6—C2—Fe1—C11	−83.2 (3)	C4—C5—Fe1—C6	120.0 (4)
C1—C2—Fe1—C11	38.0 (4)	C6—C5—Fe1—C4	−120.0 (4)
C3—C2—Fe1—C7	−166.5 (4)	C6—C5—Fe1—C9	−165.7 (4)
C6—C2—Fe1—C7	−46.9 (5)	C4—C5—Fe1—C9	−45.7 (5)
C1—C2—Fe1—C7	74.3 (5)	C6—C5—Fe1—C8	159.6 (3)
C3—C2—Fe1—C6	−119.6 (4)	C4—C5—Fe1—C8	−80.4 (3)
C1—C2—Fe1—C6	121.2 (5)	O3—C12—N1—C13	−177.8 (4)
C3—C2—Fe1—C4	−38.4 (2)	C11—C12—N1—C13	2.4 (6)
C6—C2—Fe1—C4	81.2 (3)	O3—C12—N1—C20	−1.5 (6)
C1—C2—Fe1—C4	−157.6 (4)	C11—C12—N1—C20	178.7 (3)
C3—C2—Fe1—C9	72.0 (3)	C14—C13—N1—C12	−89.5 (5)
C6—C2—Fe1—C9	−168.4 (3)	C18—C13—N1—C12	87.8 (5)
C1—C2—Fe1—C9	−47.2 (4)	C14—C13—N1—C20	94.4 (5)
C3—C2—Fe1—C8	37.6 (6)	C18—C13—N1—C20	−88.3 (5)
C6—C2—Fe1—C8	157.2 (5)	C21—C20—N1—C12	141.1 (4)
C1—C2—Fe1—C8	−81.6 (7)	C35—C20—N1—C12	−84.8 (4)
C3—C2—Fe1—C5	−82.0 (3)	C21—C20—N1—C13	−42.6 (5)
C6—C2—Fe1—C5	37.6 (3)	C35—C20—N1—C13	91.5 (4)
C1—C2—Fe1—C5	158.8 (4)	O5—C35—N2—C36	2.0 (6)
C9—C10—Fe1—C3	−80.1 (3)	C20—C35—N2—C36	−174.3 (3)
C11—C10—Fe1—C3	160.4 (2)	C39—C36—N2—C35	63.6 (5)
C9—C10—Fe1—C2	−123.7 (3)	C37—C36—N2—C35	−177.7 (4)
C11—C10—Fe1—C2	116.8 (2)	C38—C36—N2—C35	−58.8 (5)
C9—C10—Fe1—C11	119.4 (3)	C17—C16—O4—C19	−162.1 (4)
C9—C10—Fe1—C7	81.0 (3)	C15—C16—O4—C19	19.4 (6)
C11—C10—Fe1—C7	−38.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Cl2	0.93	2.82	3.641 (5)	148
C7—H7···Cg5	0.93	2.42	3.221 (2)	144
O2—H2A···O3^i	0.82	1.83	2.625 (4)	163
N2—H2···O1^i	0.86	2.51	3.010 (5)	118
C8—H8···O5^ii	0.93	2.59	3.442 (5)	153
C40—H40B···O1^iii	0.97	2.37	3.287 (6)	158
C19—H19A···Cg5^iv	0.93	2.77	3.653 (2)	139

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x+1/2, −y+3/2, z+1/2; (iv) −x+1, −y+1, −z+1.

(II) (S)-2-(Anthracen-9-yl)-N-tert-butyl-2-[N-(4-methylphenyl)ferrocenylformamido]acetamide

Crystal data

[Fe(C5H5)(C33H31N2O2)]	F(000) = 1280
Mr = 608.54	Dx = 1.326 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
a = 13.0787 (3) Å	Cell parameters from 4488 reflections
b = 14.4271 (4) Å	θ = 3.3–28.6°
c = 16.1873 (4) Å	µ = 0.53 mm^−1
β = 93.491 (2)°	T = 100 K
V = 3048.69 (13) Å^3	Block, clear light orange
Z = 4	0.26 × 0.18 × 0.08 mm

Data collection

Agilent SuperNova Dual diffractometer (Cu at zero) with Eos detector	6310 independent reflections
Radiation source: SuperNova (Mo) X-ray source	4939 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 16.0793 pixels mm^-1	θmax = 26.5°, θmin = 3.1°
ω scans	h = −10→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −18→14
Tmin = 0.930, Tmax = 1.000	l = −20→20
15717 measured 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.021P)^2 + 2.6244P] where P = (Fo^2 + 2Fc^2)/3
6310 reflections	(Δ/σ)max = 0.032
392 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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)
C1	−0.11539 (17)	0.41012 (18)	0.21338 (15)	0.0247 (6)
H1	−0.0760	0.3623	0.2372	0.030*
C2	−0.14823 (16)	0.41800 (17)	0.12824 (15)	0.0233 (5)
H2A	−0.1345	0.3763	0.0865	0.028*
C3	−0.20598 (16)	0.50134 (18)	0.11856 (15)	0.0231 (5)
H3	−0.2364	0.5238	0.0691	0.028*
C4	−0.20913 (16)	0.54414 (18)	0.19693 (15)	0.0256 (6)
H4	−0.2421	0.5995	0.2081	0.031*
C5	−0.15326 (17)	0.48786 (19)	0.25549 (15)	0.0263 (6)
H5	−0.1432	0.4999	0.3118	0.032*
C6	0.05024 (15)	0.60855 (16)	0.22502 (14)	0.0183 (5)
H6	0.0559	0.6226	0.2812	0.022*
C7	−0.00200 (16)	0.66207 (16)	0.16209 (15)	0.0214 (5)
H7	−0.0371	0.7171	0.1702	0.026*
C8	0.00810 (16)	0.61790 (17)	0.08485 (15)	0.0214 (5)
H8	−0.0184	0.6394	0.0338	0.026*
C9	0.06537 (15)	0.53548 (17)	0.09868 (14)	0.0185 (5)
H9	0.0823	0.4932	0.0584	0.022*
C10	0.09298 (15)	0.52847 (16)	0.18631 (13)	0.0146 (5)
C11	0.14351 (15)	0.44297 (16)	0.22016 (13)	0.0152 (5)
C12	0.19042 (15)	0.52056 (15)	0.35393 (13)	0.0133 (4)
C13	0.12906 (16)	0.53121 (16)	0.42042 (14)	0.0196 (5)
H13	0.0820	0.4855	0.4322	0.023*
C14	0.13834 (17)	0.61077 (17)	0.46952 (15)	0.0235 (5)
H14	0.0979	0.6171	0.5145	0.028*
C15	0.20725 (17)	0.68075 (17)	0.45214 (14)	0.0216 (5)
C16	0.26750 (16)	0.66933 (16)	0.38452 (14)	0.0186 (5)
H16	0.3130	0.7158	0.3713	0.022*
C17	0.26036 (15)	0.58950 (16)	0.33686 (13)	0.0158 (5)
H17	0.3026	0.5820	0.2932	0.019*
C19	0.22114 (15)	0.35006 (15)	0.33173 (13)	0.0133 (4)
H19	0.2415	0.3178	0.2820	0.016*
C20	0.32091 (15)	0.36085 (15)	0.38586 (14)	0.0159 (5)
C21	0.41108 (16)	0.37332 (15)	0.34252 (14)	0.0178 (5)
C22	0.41354 (17)	0.36987 (16)	0.25448 (15)	0.0223 (5)
H22	0.3524	0.3630	0.2226	0.027*
C23	0.50309 (17)	0.37639 (18)	0.21606 (16)	0.0282 (6)
H23	0.5022	0.3703	0.1588	0.034*
C24	0.59774 (17)	0.39231 (18)	0.26139 (17)	0.0287 (6)
H24	0.6579	0.3980	0.2341	0.034*
C25	0.59944 (17)	0.39904 (17)	0.34458 (17)	0.0258 (6)
H25	0.6612	0.4113	0.3741	0.031*
C26	0.50801 (16)	0.38776 (15)	0.38889 (15)	0.0199 (5)
C27	0.51170 (17)	0.38488 (17)	0.47418 (16)	0.0242 (5)
H27	0.5740	0.3951	0.5036	0.029*
C28	0.42527 (17)	0.36713 (16)	0.51752 (15)	0.0215 (5)
C29	0.43257 (18)	0.35686 (19)	0.60557 (15)	0.0288 (6)
H29	0.4963	0.3622	0.6339	0.035*
C30	0.34983 (19)	0.33972 (19)	0.64863 (15)	0.0296 (6)
H30	0.3570	0.3305	0.7056	0.035*
C31	0.25123 (18)	0.33573 (17)	0.60641 (15)	0.0255 (6)
H31	0.1937	0.3261	0.6364	0.031*
C32	0.23980 (17)	0.34576 (16)	0.52269 (14)	0.0193 (5)
H32	0.1743	0.3445	0.4969	0.023*
C33	0.32623 (16)	0.35819 (15)	0.47301 (14)	0.0169 (5)
C34	0.13460 (15)	0.28973 (15)	0.36410 (12)	0.0137 (4)
C35	0.09745 (15)	0.12597 (16)	0.40741 (13)	0.0153 (5)
C36	0.16143 (16)	0.03763 (16)	0.40722 (14)	0.0184 (5)
H36A	0.1753	0.0220	0.3513	0.028*
H36B	0.1244	−0.0121	0.4312	0.028*
H36C	0.2249	0.0474	0.4390	0.028*
C37	0.07002 (17)	0.14834 (17)	0.49584 (13)	0.0212 (5)
H37A	0.1317	0.1544	0.5308	0.032*
H37B	0.0288	0.0992	0.5162	0.032*
H37C	0.0324	0.2054	0.4960	0.032*
C38	0.00041 (16)	0.11440 (17)	0.35023 (14)	0.0202 (5)
H38A	−0.0374	0.1715	0.3481	0.030*
H38B	−0.0413	0.0661	0.3712	0.030*
H38C	0.0192	0.0984	0.2956	0.030*
Fe1	−0.06147 (2)	0.53089 (2)	0.165667 (19)	0.01444 (9)
N1	0.18131 (13)	0.44009 (12)	0.30131 (11)	0.0142 (4)
N2	0.16260 (12)	0.20052 (13)	0.37546 (10)	0.0143 (4)
H2	0.2235	0.1855	0.3631	0.017*
O1	0.15019 (11)	0.37468 (11)	0.17478 (9)	0.0211 (4)
O2	0.04832 (10)	0.31972 (11)	0.37372 (9)	0.0179 (3)
C18	0.2190 (2)	0.76654 (19)	0.50549 (17)	0.0347 (7)	0.434 (15)
H18A	0.1743	0.7623	0.5503	0.052*	0.434 (15)
H18B	0.2014	0.8203	0.4727	0.052*	0.434 (15)
H18C	0.2886	0.7715	0.5274	0.052*	0.434 (15)
C18'	0.2190 (2)	0.76654 (19)	0.50549 (17)	0.0347 (7)	0.566 (15)
H18D	0.1541	0.7822	0.5264	0.052*	0.566 (15)
H18E	0.2425	0.8170	0.4730	0.052*	0.566 (15)
H18F	0.2678	0.7548	0.5510	0.052*	0.566 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0183 (11)	0.0223 (14)	0.0334 (14)	−0.0062 (10)	0.0012 (10)	0.0084 (12)
C2	0.0208 (11)	0.0210 (13)	0.0283 (13)	−0.0083 (10)	0.0037 (10)	−0.0062 (11)
C3	0.0145 (10)	0.0292 (14)	0.0252 (13)	−0.0029 (10)	−0.0036 (9)	0.0023 (11)
C4	0.0139 (10)	0.0310 (15)	0.0324 (14)	0.0003 (10)	0.0063 (10)	−0.0053 (12)
C5	0.0205 (11)	0.0406 (17)	0.0180 (12)	−0.0098 (11)	0.0032 (10)	0.0000 (12)
C6	0.0168 (10)	0.0154 (12)	0.0220 (12)	−0.0010 (9)	−0.0036 (9)	−0.0015 (10)
C7	0.0182 (11)	0.0119 (12)	0.0334 (14)	−0.0025 (9)	−0.0037 (10)	0.0026 (11)
C8	0.0188 (11)	0.0220 (13)	0.0231 (12)	−0.0026 (10)	0.0002 (9)	0.0100 (11)
C9	0.0148 (10)	0.0218 (13)	0.0192 (11)	−0.0017 (10)	0.0028 (9)	0.0016 (10)
C10	0.0105 (9)	0.0145 (12)	0.0189 (11)	−0.0010 (9)	0.0002 (8)	0.0011 (10)
C11	0.0097 (9)	0.0165 (12)	0.0196 (11)	−0.0007 (9)	0.0025 (8)	0.0003 (10)
C12	0.0143 (10)	0.0102 (11)	0.0150 (10)	0.0029 (9)	−0.0027 (8)	0.0014 (9)
C13	0.0200 (11)	0.0161 (12)	0.0230 (12)	−0.0004 (10)	0.0049 (9)	0.0017 (10)
C14	0.0252 (12)	0.0241 (14)	0.0217 (12)	0.0063 (11)	0.0053 (10)	−0.0031 (11)
C15	0.0228 (11)	0.0176 (13)	0.0239 (12)	0.0044 (10)	−0.0046 (10)	−0.0044 (11)
C16	0.0151 (10)	0.0144 (12)	0.0255 (12)	−0.0012 (9)	−0.0035 (9)	0.0000 (10)
C17	0.0144 (10)	0.0171 (12)	0.0159 (11)	0.0004 (9)	−0.0003 (8)	0.0017 (10)
C19	0.0148 (10)	0.0100 (11)	0.0152 (11)	0.0017 (9)	0.0010 (8)	0.0005 (9)
C20	0.0152 (10)	0.0086 (11)	0.0234 (12)	0.0011 (9)	−0.0026 (9)	−0.0001 (10)
C21	0.0162 (10)	0.0083 (11)	0.0289 (13)	0.0016 (9)	0.0013 (9)	0.0043 (10)
C22	0.0202 (11)	0.0208 (13)	0.0259 (13)	0.0036 (10)	0.0016 (10)	0.0102 (11)
C23	0.0252 (12)	0.0294 (15)	0.0305 (14)	0.0037 (11)	0.0073 (11)	0.0148 (12)
C24	0.0175 (11)	0.0261 (15)	0.0434 (16)	−0.0011 (10)	0.0106 (11)	0.0151 (13)
C25	0.0144 (10)	0.0154 (13)	0.0473 (16)	−0.0010 (10)	0.0008 (10)	0.0053 (12)
C26	0.0166 (10)	0.0078 (11)	0.0350 (14)	0.0004 (9)	−0.0017 (10)	−0.0004 (10)
C27	0.0165 (11)	0.0175 (13)	0.0374 (15)	−0.0004 (10)	−0.0067 (10)	−0.0078 (11)
C28	0.0199 (11)	0.0169 (13)	0.0267 (13)	0.0030 (10)	−0.0054 (10)	−0.0067 (11)
C29	0.0239 (12)	0.0355 (16)	0.0259 (13)	0.0094 (11)	−0.0080 (10)	−0.0149 (12)
C30	0.0357 (14)	0.0344 (16)	0.0178 (12)	0.0101 (12)	−0.0052 (11)	−0.0099 (12)
C31	0.0287 (13)	0.0251 (14)	0.0229 (13)	0.0049 (11)	0.0046 (10)	−0.0080 (11)
C32	0.0210 (11)	0.0164 (13)	0.0202 (12)	0.0013 (10)	−0.0021 (9)	−0.0061 (10)
C33	0.0173 (10)	0.0099 (11)	0.0233 (12)	0.0016 (9)	−0.0018 (9)	−0.0038 (10)
C34	0.0160 (10)	0.0142 (12)	0.0106 (10)	−0.0013 (9)	−0.0016 (8)	−0.0026 (9)
C35	0.0151 (10)	0.0167 (12)	0.0144 (11)	−0.0033 (9)	0.0025 (8)	0.0024 (10)
C36	0.0197 (11)	0.0144 (12)	0.0212 (12)	−0.0024 (10)	0.0018 (9)	0.0042 (10)
C37	0.0221 (11)	0.0235 (14)	0.0186 (12)	−0.0031 (10)	0.0051 (9)	0.0036 (10)
C38	0.0163 (10)	0.0192 (13)	0.0248 (12)	−0.0027 (10)	−0.0011 (9)	−0.0007 (10)
Fe1	0.01275 (15)	0.01403 (18)	0.01644 (17)	−0.00048 (13)	0.00004 (12)	−0.00028 (14)
N1	0.0156 (9)	0.0106 (10)	0.0164 (9)	0.0004 (7)	0.0004 (7)	0.0006 (8)
N2	0.0109 (8)	0.0156 (10)	0.0167 (9)	−0.0003 (7)	0.0026 (7)	0.0010 (8)
O1	0.0243 (8)	0.0178 (9)	0.0209 (8)	0.0059 (7)	−0.0019 (7)	−0.0044 (7)
O2	0.0147 (7)	0.0164 (9)	0.0226 (8)	0.0022 (6)	0.0020 (6)	0.0006 (7)
C18	0.0350 (14)	0.0271 (16)	0.0413 (16)	0.0042 (12)	−0.0031 (12)	−0.0152 (13)
C18'	0.0350 (14)	0.0271 (16)	0.0413 (16)	0.0042 (12)	−0.0031 (12)	−0.0152 (13)

Geometric parameters (Å, º)

C1—C5	1.417 (3)	C19—C34	1.544 (3)
C1—C2	1.423 (3)	C19—H19	0.9800
C1—Fe1	2.049 (2)	C20—C33	1.409 (3)
C1—H1	0.9300	C20—C21	1.420 (3)
C2—C3	1.424 (3)	C21—C22	1.428 (3)
C2—Fe1	2.055 (2)	C21—C26	1.448 (3)
C2—H2A	0.9300	C22—C23	1.362 (3)
C3—C4	1.414 (3)	C22—H22	0.9300
C3—Fe1	2.040 (2)	C23—C24	1.419 (3)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.417 (3)	C24—C25	1.349 (4)
C4—Fe1	2.035 (2)	C24—H24	0.9300
C4—H4	0.9300	C25—C26	1.441 (3)
C5—Fe1	2.038 (2)	C25—H25	0.9300
C5—H5	0.9300	C26—C27	1.379 (3)
C6—C7	1.420 (3)	C27—C28	1.390 (3)
C6—C10	1.443 (3)	C27—H27	0.9300
C6—Fe1	2.035 (2)	C28—C29	1.430 (3)
C6—H6	0.9300	C28—C33	1.449 (3)
C7—C8	1.417 (3)	C29—C30	1.345 (3)
C7—Fe1	2.048 (2)	C29—H29	0.9300
C7—H7	0.9300	C30—C31	1.423 (3)
C8—C9	1.416 (3)	C30—H30	0.9300
C8—Fe1	2.064 (2)	C31—C32	1.362 (3)
C8—H8	0.9300	C31—H31	0.9300
C9—C10	1.446 (3)	C32—C33	1.438 (3)
C9—Fe1	2.037 (2)	C32—H32	0.9300
C9—H9	0.9300	C34—O2	1.227 (2)
C10—C11	1.488 (3)	C34—N2	1.348 (3)
C10—Fe1	2.0275 (19)	C35—N2	1.485 (3)
C11—O1	1.235 (3)	C35—C36	1.525 (3)
C11—N1	1.376 (3)	C35—C37	1.531 (3)
C12—C13	1.390 (3)	C35—C38	1.534 (3)
C12—C17	1.390 (3)	C36—H36A	0.9600
C12—N1	1.441 (3)	C36—H36B	0.9600
C13—C14	1.397 (3)	C36—H36C	0.9600
C13—H13	0.9300	C37—H37A	0.9600
C14—C15	1.393 (3)	C37—H37B	0.9600
C14—H14	0.9300	C37—H37C	0.9600
C15—C16	1.397 (3)	C38—H38A	0.9600
C15—C18	1.512 (3)	C38—H38B	0.9600
C16—C17	1.386 (3)	C38—H38C	0.9600
C16—H16	0.9300	N2—H2	0.8600
C17—H17	0.9300	C18—H18A	0.9600
C19—N1	1.473 (3)	C18—H18B	0.9600
C19—C20	1.535 (3)	C18—H18C	0.9600
C5—C1—C2	108.0 (2)	C25—C26—C21	119.0 (2)
C5—C1—Fe1	69.30 (14)	C26—C27—C28	122.1 (2)
C2—C1—Fe1	69.97 (13)	C26—C27—H27	119.0
C5—C1—H1	126.0	C28—C27—H27	119.0
C2—C1—H1	126.0	C27—C28—C29	121.0 (2)
Fe1—C1—H1	126.3	C27—C28—C33	119.7 (2)
C1—C2—C3	107.5 (2)	C29—C28—C33	119.3 (2)
C1—C2—Fe1	69.46 (13)	C30—C29—C28	121.9 (2)
C3—C2—Fe1	69.07 (13)	C30—C29—H29	119.1
C1—C2—H2A	126.2	C28—C29—H29	119.1
C3—C2—H2A	126.2	C29—C30—C31	119.5 (2)
Fe1—C2—H2A	126.8	C29—C30—H30	120.3
C4—C3—C2	108.3 (2)	C31—C30—H30	120.3
C4—C3—Fe1	69.52 (12)	C32—C31—C30	121.0 (2)
C2—C3—Fe1	70.24 (12)	C32—C31—H31	119.5
C4—C3—H3	125.8	C30—C31—H31	119.5
C2—C3—H3	125.8	C31—C32—C33	121.8 (2)
Fe1—C3—H3	126.0	C31—C32—H32	119.1
C3—C4—C5	107.9 (2)	C33—C32—H32	119.1
C3—C4—Fe1	69.87 (13)	C20—C33—C32	124.82 (19)
C5—C4—Fe1	69.76 (12)	C20—C33—C28	118.9 (2)
C3—C4—H4	126.0	C32—C33—C28	116.3 (2)
C5—C4—H4	126.0	O2—C34—N2	124.3 (2)
Fe1—C4—H4	125.9	O2—C34—C19	122.9 (2)
C4—C5—C1	108.2 (2)	N2—C34—C19	112.70 (17)
C4—C5—Fe1	69.54 (13)	N2—C35—C36	106.15 (16)
C1—C5—Fe1	70.11 (13)	N2—C35—C37	110.18 (18)
C4—C5—H5	125.9	C36—C35—C37	109.75 (18)
C1—C5—H5	125.9	N2—C35—C38	109.88 (17)
Fe1—C5—H5	126.1	C36—C35—C38	110.00 (18)
C7—C6—C10	107.8 (2)	C37—C35—C38	110.78 (17)
C7—C6—Fe1	70.15 (12)	C35—C36—H36A	109.5
C10—C6—Fe1	68.91 (12)	C35—C36—H36B	109.5
C7—C6—H6	126.1	H36A—C36—H36B	109.5
C10—C6—H6	126.1	C35—C36—H36C	109.5
Fe1—C6—H6	126.4	H36A—C36—H36C	109.5
C8—C7—C6	108.8 (2)	H36B—C36—H36C	109.5
C8—C7—Fe1	70.45 (13)	C35—C37—H37A	109.5
C6—C7—Fe1	69.16 (13)	C35—C37—H37B	109.5
C8—C7—H7	125.6	H37A—C37—H37B	109.5
C6—C7—H7	125.6	C35—C37—H37C	109.5
Fe1—C7—H7	126.4	H37A—C37—H37C	109.5
C9—C8—C7	108.4 (2)	H37B—C37—H37C	109.5
C9—C8—Fe1	68.80 (12)	C35—C38—H38A	109.5
C7—C8—Fe1	69.25 (13)	C35—C38—H38B	109.5
C9—C8—H8	125.8	H38A—C38—H38B	109.5
C7—C8—H8	125.8	C35—C38—H38C	109.5
Fe1—C8—H8	127.7	H38A—C38—H38C	109.5
C8—C9—C10	108.2 (2)	H38B—C38—H38C	109.5
C8—C9—Fe1	70.81 (13)	C10—Fe1—C4	155.73 (9)
C10—C9—Fe1	68.80 (11)	C10—Fe1—C6	41.61 (8)
C8—C9—H9	125.9	C4—Fe1—C6	119.72 (10)
C10—C9—H9	125.9	C10—Fe1—C9	41.67 (8)
Fe1—C9—H9	126.0	C4—Fe1—C9	160.92 (9)
C6—C10—C9	106.85 (19)	C6—Fe1—C9	69.45 (9)
C6—C10—C11	132.76 (19)	C10—Fe1—C5	120.10 (9)
C9—C10—C11	119.86 (19)	C4—Fe1—C5	40.71 (10)
C6—C10—Fe1	69.48 (11)	C6—Fe1—C5	105.55 (9)
C9—C10—Fe1	69.53 (11)	C9—Fe1—C5	157.47 (10)
C11—C10—Fe1	119.38 (14)	C10—Fe1—C3	161.67 (9)
O1—C11—N1	120.6 (2)	C4—Fe1—C3	40.61 (9)
O1—C11—C10	119.22 (19)	C6—Fe1—C3	156.04 (10)
N1—C11—C10	120.15 (19)	C9—Fe1—C3	125.01 (9)
C13—C12—C17	119.5 (2)	C5—Fe1—C3	68.30 (9)
C13—C12—N1	121.08 (19)	C10—Fe1—C7	69.17 (9)
C17—C12—N1	119.39 (19)	C4—Fe1—C7	106.74 (10)
C12—C13—C14	119.8 (2)	C6—Fe1—C7	40.69 (9)
C12—C13—H13	120.1	C9—Fe1—C7	68.41 (10)
C14—C13—H13	120.1	C5—Fe1—C7	122.87 (10)
C15—C14—C13	121.0 (2)	C3—Fe1—C7	121.83 (9)
C15—C14—H14	119.5	C10—Fe1—C1	106.60 (9)
C13—C14—H14	119.5	C4—Fe1—C1	68.43 (10)
C14—C15—C16	118.4 (2)	C6—Fe1—C1	122.96 (9)
C14—C15—C18	121.5 (2)	C9—Fe1—C1	122.58 (10)
C16—C15—C18	120.1 (2)	C5—Fe1—C1	40.59 (10)
C17—C16—C15	120.8 (2)	C3—Fe1—C1	68.33 (9)
C17—C16—H16	119.6	C7—Fe1—C1	159.49 (10)
C15—C16—H16	119.6	C10—Fe1—C2	124.17 (9)
C16—C17—C12	120.4 (2)	C4—Fe1—C2	68.43 (10)
C16—C17—H17	119.8	C6—Fe1—C2	160.57 (9)
C12—C17—H17	119.8	C9—Fe1—C2	108.76 (9)
N1—C19—C20	111.87 (17)	C5—Fe1—C2	68.30 (10)
N1—C19—C34	111.03 (16)	C3—Fe1—C2	40.68 (9)
C20—C19—C34	118.60 (17)	C7—Fe1—C2	158.08 (9)
N1—C19—H19	104.6	C1—Fe1—C2	40.57 (9)
C20—C19—H19	104.6	C10—Fe1—C8	69.01 (9)
C34—C19—H19	104.6	C4—Fe1—C8	124.20 (10)
C33—C20—C21	120.42 (19)	C6—Fe1—C8	68.46 (9)
C33—C20—C19	123.88 (19)	C9—Fe1—C8	40.39 (9)
C21—C20—C19	115.70 (19)	C5—Fe1—C8	159.89 (10)
C20—C21—C22	124.0 (2)	C3—Fe1—C8	108.93 (9)
C20—C21—C26	119.3 (2)	C7—Fe1—C8	40.30 (9)
C22—C21—C26	116.7 (2)	C1—Fe1—C8	158.67 (10)
C23—C22—C21	121.7 (2)	C2—Fe1—C8	123.50 (9)
C23—C22—H22	119.2	C11—N1—C12	123.52 (18)
C21—C22—H22	119.2	C11—N1—C19	116.43 (17)
C22—C23—C24	121.5 (2)	C12—N1—C19	119.88 (16)
C22—C23—H23	119.3	C34—N2—C35	125.63 (17)
C24—C23—H23	119.3	C34—N2—H2	117.2
C25—C24—C23	119.3 (2)	C35—N2—H2	117.2
C25—C24—H24	120.4	C15—C18—H18A	109.5
C23—C24—H24	120.4	C15—C18—H18B	109.5
C24—C25—C26	121.7 (2)	H18A—C18—H18B	109.5
C24—C25—H25	119.2	C15—C18—H18C	109.5
C26—C25—H25	119.2	H18A—C18—H18C	109.5
C27—C26—C25	121.5 (2)	H18B—C18—H18C	109.5
C27—C26—C21	119.4 (2)
C5—C1—C2—C3	0.3 (2)	C10—C6—Fe1—C5	118.07 (14)
Fe1—C1—C2—C3	−58.78 (15)	C7—C6—Fe1—C3	−51.3 (3)
C5—C1—C2—Fe1	59.08 (16)	C10—C6—Fe1—C3	−170.5 (2)
C1—C2—C3—C4	−0.3 (2)	C10—C6—Fe1—C7	−119.21 (19)
Fe1—C2—C3—C4	−59.30 (16)	C7—C6—Fe1—C1	−163.35 (14)
C1—C2—C3—Fe1	59.03 (15)	C10—C6—Fe1—C1	77.44 (15)
C2—C3—C4—C5	0.2 (3)	C7—C6—Fe1—C2	168.7 (3)
Fe1—C3—C4—C5	−59.60 (15)	C10—C6—Fe1—C2	49.5 (3)
C2—C3—C4—Fe1	59.75 (15)	C7—C6—Fe1—C8	37.00 (14)
C3—C4—C5—C1	0.0 (3)	C10—C6—Fe1—C8	−82.21 (14)
Fe1—C4—C5—C1	−59.65 (16)	C8—C9—Fe1—C10	−119.29 (19)
C3—C4—C5—Fe1	59.67 (16)	C8—C9—Fe1—C4	41.9 (4)
C2—C1—C5—C4	−0.2 (3)	C10—C9—Fe1—C4	161.2 (3)
Fe1—C1—C5—C4	59.29 (16)	C8—C9—Fe1—C6	−80.53 (14)
C2—C1—C5—Fe1	−59.49 (15)	C10—C9—Fe1—C6	38.75 (13)
C10—C6—C7—C8	−0.7 (2)	C8—C9—Fe1—C5	−161.5 (2)
Fe1—C6—C7—C8	−59.49 (15)	C10—C9—Fe1—C5	−42.2 (3)
C10—C6—C7—Fe1	58.81 (14)	C8—C9—Fe1—C3	77.74 (17)
C6—C7—C8—C9	0.9 (2)	C10—C9—Fe1—C3	−162.97 (13)
Fe1—C7—C8—C9	−57.78 (15)	C8—C9—Fe1—C7	−36.80 (13)
C6—C7—C8—Fe1	58.70 (15)	C10—C9—Fe1—C7	82.49 (14)
C7—C8—C9—C10	−0.8 (2)	C8—C9—Fe1—C1	162.72 (13)
Fe1—C8—C9—C10	−58.85 (14)	C10—C9—Fe1—C1	−77.99 (16)
C7—C8—C9—Fe1	58.05 (15)	C8—C9—Fe1—C2	120.02 (14)
C7—C6—C10—C9	0.2 (2)	C10—C9—Fe1—C2	−120.69 (14)
Fe1—C6—C10—C9	59.77 (14)	C10—C9—Fe1—C8	119.29 (19)
C7—C6—C10—C11	−171.1 (2)	C4—C5—Fe1—C10	160.38 (14)
Fe1—C6—C10—C11	−111.6 (2)	C1—C5—Fe1—C10	−80.27 (16)
C7—C6—C10—Fe1	−59.58 (15)	C1—C5—Fe1—C4	119.4 (2)
C8—C9—C10—C6	0.4 (2)	C4—C5—Fe1—C6	117.74 (15)
Fe1—C9—C10—C6	−59.73 (14)	C1—C5—Fe1—C6	−122.90 (14)
C8—C9—C10—C11	173.04 (18)	C4—C5—Fe1—C9	−168.5 (2)
Fe1—C9—C10—C11	112.93 (18)	C1—C5—Fe1—C9	−49.2 (3)
C8—C9—C10—Fe1	60.11 (15)	C4—C5—Fe1—C3	−37.78 (15)
C6—C10—C11—O1	161.8 (2)	C1—C5—Fe1—C3	81.57 (15)
C9—C10—C11—O1	−8.6 (3)	C4—C5—Fe1—C7	76.97 (17)
Fe1—C10—C11—O1	73.3 (2)	C1—C5—Fe1—C7	−163.68 (13)
C6—C10—C11—N1	−17.6 (3)	C4—C5—Fe1—C1	−119.4 (2)
C9—C10—C11—N1	172.00 (18)	C4—C5—Fe1—C2	−81.72 (15)
Fe1—C10—C11—N1	−106.02 (19)	C1—C5—Fe1—C2	37.63 (14)
C17—C12—C13—C14	−0.2 (3)	C4—C5—Fe1—C8	48.1 (3)
N1—C12—C13—C14	−178.87 (19)	C1—C5—Fe1—C8	167.5 (2)
C12—C13—C14—C15	1.1 (3)	C4—C3—Fe1—C10	158.9 (3)
C13—C14—C15—C16	−0.3 (3)	C2—C3—Fe1—C10	39.5 (4)
C13—C14—C15—C18	−179.2 (2)	C2—C3—Fe1—C4	−119.4 (2)
C14—C15—C16—C17	−1.3 (3)	C4—C3—Fe1—C6	−41.5 (3)
C18—C15—C16—C17	177.6 (2)	C2—C3—Fe1—C6	−160.9 (2)
C15—C16—C17—C12	2.2 (3)	C4—C3—Fe1—C9	−162.89 (15)
C13—C12—C17—C16	−1.4 (3)	C2—C3—Fe1—C9	77.73 (17)
N1—C12—C17—C16	177.31 (18)	C4—C3—Fe1—C5	37.87 (15)
N1—C19—C20—C33	100.9 (2)	C2—C3—Fe1—C5	−81.51 (15)
C34—C19—C20—C33	−30.3 (3)	C4—C3—Fe1—C7	−78.27 (17)
N1—C19—C20—C21	−79.6 (2)	C2—C3—Fe1—C7	162.35 (14)
C34—C19—C20—C21	149.2 (2)	C4—C3—Fe1—C1	81.71 (16)
C33—C20—C21—C22	175.1 (2)	C2—C3—Fe1—C1	−37.67 (14)
C19—C20—C21—C22	−4.4 (3)	C4—C3—Fe1—C2	119.4 (2)
C33—C20—C21—C26	−3.0 (3)	C4—C3—Fe1—C8	−120.87 (15)
C19—C20—C21—C26	177.56 (19)	C2—C3—Fe1—C8	119.75 (14)
C20—C21—C22—C23	−175.7 (2)	C8—C7—Fe1—C10	81.72 (14)
C26—C21—C22—C23	2.4 (3)	C6—C7—Fe1—C10	−38.33 (13)
C21—C22—C23—C24	−3.7 (4)	C8—C7—Fe1—C4	−123.57 (14)
C22—C23—C24—C25	1.5 (4)	C6—C7—Fe1—C4	116.38 (14)
C23—C24—C25—C26	1.9 (4)	C8—C7—Fe1—C6	120.05 (19)
C24—C25—C26—C27	173.0 (2)	C8—C7—Fe1—C9	36.87 (13)
C24—C25—C26—C21	−3.0 (4)	C6—C7—Fe1—C9	−83.18 (14)
C20—C21—C26—C27	3.0 (3)	C8—C7—Fe1—C5	−165.14 (13)
C22—C21—C26—C27	−175.2 (2)	C6—C7—Fe1—C5	74.81 (16)
C20—C21—C26—C25	179.1 (2)	C8—C7—Fe1—C3	−81.86 (15)
C22—C21—C26—C25	0.9 (3)	C6—C7—Fe1—C3	158.09 (13)
C25—C26—C27—C28	−175.1 (2)	C8—C7—Fe1—C1	163.4 (2)
C21—C26—C27—C28	1.0 (4)	C6—C7—Fe1—C1	43.3 (3)
C26—C27—C28—C29	174.7 (2)	C8—C7—Fe1—C2	−49.9 (3)
C26—C27—C28—C33	−4.8 (4)	C6—C7—Fe1—C2	−169.9 (2)
C27—C28—C29—C30	180.0 (2)	C6—C7—Fe1—C8	−120.05 (19)
C33—C28—C29—C30	−0.5 (4)	C5—C1—Fe1—C10	117.15 (14)
C28—C29—C30—C31	−2.9 (4)	C2—C1—Fe1—C10	−123.57 (14)
C29—C30—C31—C32	2.3 (4)	C5—C1—Fe1—C4	−37.68 (14)
C30—C31—C32—C33	1.7 (4)	C2—C1—Fe1—C4	81.60 (15)
C21—C20—C33—C32	−179.9 (2)	C5—C1—Fe1—C6	74.59 (16)
C19—C20—C33—C32	−0.4 (3)	C2—C1—Fe1—C6	−166.13 (13)
C21—C20—C33—C28	−0.8 (3)	C5—C1—Fe1—C9	159.88 (13)
C19—C20—C33—C28	178.6 (2)	C2—C1—Fe1—C9	−80.83 (16)
C31—C32—C33—C20	174.2 (2)	C2—C1—Fe1—C5	119.29 (19)
C31—C32—C33—C28	−4.9 (3)	C5—C1—Fe1—C3	−81.51 (14)
C27—C28—C33—C20	4.7 (3)	C2—C1—Fe1—C3	37.77 (14)
C29—C28—C33—C20	−174.9 (2)	C5—C1—Fe1—C7	42.4 (3)
C27—C28—C33—C32	−176.2 (2)	C2—C1—Fe1—C7	161.6 (2)
C29—C28—C33—C32	4.3 (3)	C5—C1—Fe1—C2	−119.29 (19)
N1—C19—C34—O2	−9.8 (3)	C5—C1—Fe1—C8	−168.2 (2)
C20—C19—C34—O2	121.8 (2)	C2—C1—Fe1—C8	−48.9 (3)
N1—C19—C34—N2	166.39 (17)	C1—C2—Fe1—C10	74.82 (16)
C20—C19—C34—N2	−62.0 (2)	C3—C2—Fe1—C10	−166.01 (13)
C6—C10—Fe1—C4	−47.1 (3)	C1—C2—Fe1—C4	−81.59 (15)
C9—C10—Fe1—C4	−165.1 (2)	C3—C2—Fe1—C4	37.58 (14)
C11—C10—Fe1—C4	81.3 (3)	C1—C2—Fe1—C6	37.2 (3)
C9—C10—Fe1—C6	−118.04 (19)	C3—C2—Fe1—C6	156.4 (3)
C11—C10—Fe1—C6	128.4 (2)	C1—C2—Fe1—C9	118.53 (14)
C6—C10—Fe1—C9	118.04 (19)	C3—C2—Fe1—C9	−122.30 (14)
C11—C10—Fe1—C9	−113.6 (2)	C1—C2—Fe1—C5	−37.65 (14)
C6—C10—Fe1—C5	−79.28 (16)	C3—C2—Fe1—C5	81.53 (15)
C9—C10—Fe1—C5	162.68 (14)	C1—C2—Fe1—C3	−119.2 (2)
C11—C10—Fe1—C5	49.1 (2)	C1—C2—Fe1—C7	−162.8 (2)
C6—C10—Fe1—C3	167.7 (3)	C3—C2—Fe1—C7	−43.6 (3)
C9—C10—Fe1—C3	49.7 (3)	C3—C2—Fe1—C1	119.2 (2)
C11—C10—Fe1—C3	−63.9 (4)	C1—C2—Fe1—C8	160.81 (13)
C6—C10—Fe1—C7	37.51 (13)	C3—C2—Fe1—C8	−80.02 (16)
C9—C10—Fe1—C7	−80.53 (14)	C9—C8—Fe1—C10	38.40 (13)
C11—C10—Fe1—C7	165.91 (19)	C7—C8—Fe1—C10	−82.16 (14)
C6—C10—Fe1—C1	−121.29 (14)	C9—C8—Fe1—C4	−164.70 (13)
C9—C10—Fe1—C1	120.68 (14)	C7—C8—Fe1—C4	74.74 (16)
C11—C10—Fe1—C1	7.11 (19)	C9—C8—Fe1—C6	83.20 (14)
C6—C10—Fe1—C2	−162.21 (13)	C7—C8—Fe1—C6	−37.35 (13)
C9—C10—Fe1—C2	79.75 (16)	C7—C8—Fe1—C9	−120.55 (18)
C11—C10—Fe1—C2	−33.8 (2)	C9—C8—Fe1—C5	159.3 (2)
C6—C10—Fe1—C8	80.79 (14)	C7—C8—Fe1—C5	38.8 (3)
C9—C10—Fe1—C8	−37.25 (14)	C9—C8—Fe1—C3	−122.21 (14)
C11—C10—Fe1—C8	−150.81 (19)	C7—C8—Fe1—C3	117.24 (14)
C3—C4—Fe1—C10	−164.0 (2)	C9—C8—Fe1—C7	120.55 (18)
C5—C4—Fe1—C10	−45.0 (3)	C9—C8—Fe1—C1	−43.5 (3)
C3—C4—Fe1—C6	161.96 (14)	C7—C8—Fe1—C1	−164.0 (2)
C5—C4—Fe1—C6	−79.04 (17)	C9—C8—Fe1—C2	−79.47 (15)
C3—C4—Fe1—C9	47.5 (4)	C7—C8—Fe1—C2	159.98 (13)
C5—C4—Fe1—C9	166.5 (3)	O1—C11—N1—C12	170.15 (19)
C3—C4—Fe1—C5	−119.0 (2)	C10—C11—N1—C12	−10.5 (3)
C5—C4—Fe1—C3	119.0 (2)	O1—C11—N1—C19	−5.0 (3)
C3—C4—Fe1—C7	119.69 (15)	C10—C11—N1—C19	174.35 (17)
C5—C4—Fe1—C7	−121.30 (15)	C13—C12—N1—C11	111.4 (2)
C3—C4—Fe1—C1	−81.43 (16)	C17—C12—N1—C11	−67.3 (3)
C5—C4—Fe1—C1	37.58 (15)	C13—C12—N1—C19	−73.6 (3)
C3—C4—Fe1—C2	−37.65 (15)	C17—C12—N1—C19	107.7 (2)
C5—C4—Fe1—C2	81.36 (16)	C20—C19—N1—C11	138.24 (18)
C3—C4—Fe1—C8	79.03 (18)	C34—C19—N1—C11	−86.8 (2)
C5—C4—Fe1—C8	−161.97 (15)	C20—C19—N1—C12	−37.1 (2)
C7—C6—Fe1—C10	119.21 (19)	C34—C19—N1—C12	97.9 (2)
C7—C6—Fe1—C4	−81.07 (16)	O2—C34—N2—C35	−5.1 (3)
C10—C6—Fe1—C4	159.72 (13)	C19—C34—N2—C35	178.77 (17)
C7—C6—Fe1—C9	80.40 (14)	C36—C35—N2—C34	178.70 (19)
C10—C6—Fe1—C9	−38.81 (13)	C37—C35—N2—C34	−62.5 (3)
C7—C6—Fe1—C5	−122.72 (15)	C38—C35—N2—C34	59.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1^i	0.93	2.47	3.314 (3)	152
C6—H6···Cg6	0.93	2.65	3.376 (3)	135
C7—H7···Cg7^i	0.93	2.47	3.245 (2)	141

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.