Ferrocenecarboxylic anhydride: Identification of a new polymorph

Article abstract of DOI:10.1107/S205322961701124X

A new monoclinic polymorph of ferrocenecarboxylic anhydride, [Fe₂(C₅H₅)₂(C₁₂H₈O₃)], was obtained. Three molecules are present in the asymmetric unit, two of them being nearly identical (r.m.s. deviation = 0.11 ?), with the Fe atoms on the same side of the anhydride functional group. In the third molecule, the two Fe atoms are located at opposite sides of the functional group (ferrocene-ferrocene pseudo-torsion angle = 146.2), a very unsual feature in metallocene anhydrides. A network of weak intermolecular hydrogen bonds was also disclosed.

Full text of DOI:10.1107/S205322961701124X

research papers
Ferrocenecarboxylic anhydride: identification of a
new polymorph
ISSN 2053-2296
Mehdi Tazi,a Thierry Roisnel,b Florence Mongina and William Erba*
a
´
UMR 6226, Institut des Sciences Chimiques de Rennes, Equipe Chimie Organique et Interfaces, Universite de
Rennes 1–CNRS, Campus de Beaulieu, Batiment 10A, Case 1003, 35042 Rennes Cedex, France, and bCentre de
ˆ
´
´
Diffractometrie X, Institut des Sciences Chimiques de Rennes, UMR6226, Universite de Rennes 1–CNRS, Campus de
Received 31 May 2017
Accepted 31 July 2017
ˆ
Beaulieu, Batiment 10B, 35042 Rennes Cedex, France. *Correspondence e-mail: william.erb@univ-rennes1.fr
A new monoclinic polymorph of ferrocenecarboxylic anhydride, [Fe2(C5H5)2-
(C12H8O3)], was obtained. Three molecules are present in the asymmetric unit,
Edited by D. S. Yufit, University of Durham,
England
˚
two of them being nearly identical (r.m.s. deviation = 0.11 A), with the Fe atoms
Keywords: ferrocene; acid anhydride; metallo-
cene anhydride; crystal structure; hydrogen
bonds; polymorph.
on the same side of the anhydride functional group. In the third molecule, the
two Fe atoms are located at opposite sides of the functional group (ferrocene–
ferrocene pseudo-torsion angle = 146.2ꢀ), a very unsual feature in metallocene
anhydrides. A network of weak intermolecular hydrogen bonds was also
disclosed.
CCDC reference: 1553140
Supporting information: this article has
supporting information at journals.iucr.org/c
1. Introduction
Anhydrides are a well-known class of acylation reagents
widely used in organic synthesis. While they are usually
prepared intentionally for synthetic use, serendipity some-
times leads to unexpected new compounds, as is the case for
ferrocenecarboxylic anhydride, (1) (Scheme 1). It was first
reported by Lau & Hart (1959) during studies to access
ferrocene peroxide. By refluxing ferrocenecarbonyl chloride
(FcCOCl) with sodium peroxide, they isolated (1), which was
characterized by its melting point, IR spectrum and elemental
analysis. The same year, Acton & Silverstein (1959) obtained
(1) during the synthesis of ferrocenecarboxamides from
ferrocenecarboxylic acid (FcCO2H) in the presence of di-
cyclohexylcarbodiimide. Reference samples were further
prepared by the reaction of FcCOCl with water in the
presence of pyridine. Kupchik & Kiesel (1966) reported the
unexpected formation of (1) during the reaction of FcCOCl
with tributyltin hydride, which was supposed to deliver the
corresponding ferrocenecarbaldehyde or ester. A reference
sample was also prepared, that time by reacting FcCOCl with
FcCO2Na. It was almost 40 years later that Runqiu & Qingmin
(2001) reported the formation of (1) (up to a yield of 47%)
during the synthesis of FcCOCl under the conditions
described by Lau & Hart (1959). In addition to the previously
reported melting point, IR spectrum and elemental analysis,
1
the H NMR spectrum and mass analysis of ferrocenecarb-
# 2017 International Union of Crystallography
760 https://doi.org/10.1107/S205322961701124X
Acta Cryst. (2017). C73, 760–766

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Table 1
Experimental details.
(1B) (This work)
(1A) (McAdam & Simpson, 2016)
Crystal data
Chemical formula
Mr
[Fe2(C5H5)2(C12H8O3)]
442.06
[Fe2(C5H5)2(C12H8O3)]
442.06
Crystal system, space group
Temperature (K)
Monoclinic, Cc
150
5.9758 (5), 36.456 (3), 24.363 (2)
91.997 (3)
5304.4 (8)
12
Mo Kꢁ
1.66
0.56 ꢃ 0.36 ꢃ 0.30
Orthorhombic, Pbca
100
14.8773 (2), 12.2499 (2), 19.3288 (3)
˚
a, b, c (A)
ꢀ (ꢀ)
3
˚
V (A )
3522.59 (9)
8
Cu Kꢁ
13.38
Z
Radiation type
ꢂ (mmꢂ1
Crystal size (mm)
)
0.16 ꢃ 0.13 ꢃ 0.11
Data collection
Diffractometer
Bruker APEXII
Agilent SuperNova Dual Source
diffractometer with an Atlas detector
Gaussian (CrysAlis PRO; Agilent, 2014)
0.267, 0.456
Absorption correction
Tmin, Tmax
Multi-scan (Sheldrick, 2014)
0.466, 0.608
16323, 10804, 10350
No. of measured, independent and observed
[I > 2ꢃ(I)] reflections
Rint
13584, 3468, 3262
0.023
0.649
0.040
0.621
ꢂ1
˚
(sin ꢄ/ꢅ)max (A
)
Refinement
R[F2 > 2ꢃ(F2)], wR(F2), S
No. of reflections
No. of parameters
No. of restraints
0.049, 0.119, 1.11
10804
731
32
0.030, 0.090, 0.84
3468
244
0
H-atom parameters constrained
H-atom treatment
Weighting scheme
H-atom parameters constrained
w = 1/[ꢃ2(Fo2) + (0.0346P)2 + 44.5361P]
w = 1/[ꢃ2(Fo2) + (0.089P)2 + 0.2107P]
2
where P = (Fo + 2Fc2)/3
where P = (Fo2 + 2Fc2)/3
ꢂ3
˚
Áꢆmax, Áꢆmin (e A
Absolute structure
Absolute structure parameter
)
0.97, ꢂ0.86
0.31, ꢂ0.68
Refined as in inversion twin
0.21 (3)
–
–
Computer programs: APEX2 (Bruker, 2014), SHELXT (Sheldrick, 2015a), SHELXL2016 (Sheldrick, 2015b), SXGRAPH (Farrugia, 1999), Mercury (Macrae et al., 2008) and
CRYSCALC (T. Roisnel, local program).
oxylic anhydride were described. Schetter & Speiser (2004)
also reported the formation of (1) during the reaction of
FcCO2H with various carbodiimides. Finally, in 2016,
McAdam & Simpson (2016) reported that (1) was isolated, as
a by-product, during the reaction of FcCO2H with triphos-
gene. In this case, crystals suitable for X-ray analysis were
obtained and the solid-state structure was determined.
Apart from these synthesis reports, (1) was used spor-
adically as a reagent. Wenzer was the first to use it for the
esterification of cholesterol in the presence of pyridine
(Hoffmann et al., 1980). Eckert & Koller (1990a,b) reported
the amidation of H-Phe-OtBu in the presence of trimethyl-
amine and the reaction of (1) with bovine serum albumin in
buffered solution. Kihara et al. (2004) used (1) in the synthesis
of a redox-active rotaxane. A ferrocene stopper was intro-
duced by the esterification of an alcohol in the presence of
catalytic amounts of (n-Bu)3P. The same year, Schetter &
Speiser (2004) reported the amidation of 3-(triethoxysil-
yl)propylamine with (1) in the presence of a carbodiimide in
37% yield. Finally, Halls et al. (2012) reported the post-func-
tionalization of metal–organic frameworks with (1) to access
new redox-active materials. It should be noted that, apart from
the work of Kihara et al. (2004), the yields of ester and amide
formations remain surprisingly low (20 to 47%). This lack of
reactivity was also noticed by Runqiu & Qingmin (2001), who
failed to react (1) with primary or secondary amines and with
hydrazines.
It appears that (1) is usually obtained as a by-product in the
synthesis of FcCOCl with various chlorinating reagents or
during the formation of amides in the presence of carbodi-
imides. In the course of a program dedicated to the synthesis
of new ferrocenecarboxamides (Palabindela et al., 2016), we
reacted FcCO2H with thionyl chloride to access FcCOCl.
During the purification steps, column chromatography
1
afforded an unknown product, and H and 13C NMR studies
revealed the presence of a ferrocene monosubstituted with a
carboxyl group, which was not an acid or an acyl chloride, nor
an ester. We considered that there was a possibility that a
stable anhydride had been formed; slow crystallization of the
pure product and the solid-state structure obtained by X-ray
diffraction confirmed our hypothesis. However, instead of the
known crystal structure already described by McAdam &
Simpson (2016), we managed to obtain a previously unknown
polymorph of (1). Its spectroscopic data and crystal structure
will be described here and compared to other cyclopenta-
dienecarboxylic anhydrides.
ꢁ
Acta Cryst. (2017). C73, 760–766
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[Fe2(C5H5)2(C12H8O3)] 761

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Figure 1
The structures of the orthorhombic [(1A), top] and monoclinic [(1B), bottom] polymorphs. Displacement ellipsoids are drawn at the 30% probability
level.
spectra were recorded on a Bruker Avance III at 500 and
125 MHz, respectively. 1H chemical shifts (ꢇ) are given in ppm
relative to the solvent residual peak and 13C chemical shifts
are relative to the central peak of the solvent signal. Peak
assignments were based on two-dimensional experiments. ꢈmax
(film)/cmꢂ1: 2919, 1768 (C O, sym), 1713 (C O, asym),
2. Experimental
2.1. Synthesis and crystallization
Dimethylformamide (0.1 ml) and SOCl2 (6.4 ml, 88 mmol,
2.2 equivalents) were added dropwise to a suspension of
FcCO2H (9.2 g, 40 mmol, 1.0 equivalent) in dry dichloro-
methane (110 ml) at room temperature (see Scheme 1). After
15 min, the reaction mixture was concentrated under vacuum
and the residue was dissolved in dry dichloromethane (150 ml)
before diisopropylamine (17 ml, 120 mmol, 3.0 equivalents)
was added dropwise. The reaction mixture was then stirred at
room temperature until the reaction was complete. HCl (1 M)
was added until a pH of 1 was achieved and the reaction
mixture was extracted with EtOAc. The combined organic
layers were dried over MgSO4, filtered and concentrated
under vacuum to give the crude product. Purification by
column chromatography, eluting with heptane/EtOAc
(80:20 v/v) afforded the desired FcCOCl as the main product
and the new ferrocenecarboxylic anhydride, namely poly-
morph (1B), by crystallization upon standing (yield 0.18 g, 2%;
m.p. 386–388 K).
1
1444, 1243, 1067, 1044, 1007. H NMR (500.0 MHz, CDCl3):
ꢇ 4.88 (t, J = 1.9 Hz, 4H, 4 ꢃ Fc CH), 4.54 (t, J = 1.9 Hz, 4H, 4 ꢃ
Fc CH), 4.35 (s, 10H, 10 ꢃ Fc CH). 13C NMR (125.7 MHz,
CDCl3): ꢇ 167.9 (2 ꢃ C O), 72.9 (4 ꢃ Fc CH), 71.0 (4 ꢃ Fc
CH), 70.4 (10 ꢃ Fc CH), 69.6 (2 ꢃ Fc C).
2.3. Refinement
Crystal data, data collection and structure refinement
details are summarized in Table 1. The crystal structure was
solved in the noncentrosymmetric Cc space group by a dual-
space algorithm using the SHELXT program (Sheldrick,
2015a), and then refined with full-matrix least-square methods
based on F2 (SHELXL; Sheldrick, 2015b). The structure was
refined as an inversion twin and the major twin fraction
constitutes approximately 80% of the crystal. H atoms were
included in calculated positions. In the absence of restraints or
constraints on the anisotropic displacement parameters
(ADPs) of the C51–C55 ring atoms, some B and C alerts
2.2. Spectroscopic analyses
IR spectra were taken on a PerkinElmer Spectrum 100
spectrometer. 1H and 13C Nuclear Magnetic Resonance (NMR)
ꢁ
762 Tazi et al. [Fe2(C5H5)2(C12H8O3)]
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Table 2
Hydrogen-bond geometry (A, ).
ꢀ
˚
D—Hꢄ ꢄ ꢄA
D—H
Hꢄ ꢄ ꢄA
Dꢄ ꢄ ꢄA
D—Hꢄ ꢄ ꢄA
C49—H49ꢄ ꢄ ꢄO72
C31—H31ꢄ ꢄ ꢄO12
C5—H5ꢄ ꢄ ꢄO45i
0.95
0.95
0.95
0.95
0.95
0.95
0.95
2.64
2.49
2.56
2.57
2.33
2.66
2.35
3.516 (10)
3.387 (10)
3.367 (11)
3.438 (12)
3.255 (11)
3.595 (10)
3.273 (10)
153
158
142
152
164
170
164
C85—H85ꢄ ꢄ ꢄO42ii
C6—H6ꢄ ꢄ ꢄO15iii
C39—H39ꢄ ꢄ ꢄO45iii
C69—H69ꢄ ꢄ ꢄO75iv
1
2
1
2
1
2
1
2
Symmetry codes: (i) x ꢂ ; ꢂy þ ; z þ ; (ii) x; ꢂy þ 1; z ꢂ ; (iii) x ꢂ 1; y; z; (iv)
x þ 1; y; z.
be seen that the anhydride molecules comprising the Fe1/Fe2
(molecule A) and Fe5/Fe6 (molecule C) atoms appear to be
nearly identical by a 180ꢀ rotation around the b axis. This is
confirmed by their molecular overlay (the Mercury automatic
overlay module was used; Macrae et al., 2008), with the metal
atoms (Fe1/Fe2 and Fe5/Fe6) located on the same side of the
˚
anhydride group (Fig. 3, bottom; r.m.s. deviation of 0.11 A).
Figure 2
However, a much larger difference can been seen for the
remaining anhydride molecule (molecule B), in which the two
metal atoms (namely Fe3 and Fe4) are on opposite sides of the
anhydride group, as confirmed by the overlay of the molecules
Partial packing view of monoclinic polymorph (1B), showing the
hydrogen bonds as dashed red lines. H atoms not involved in hydrogen
bonds have been omitted for clarity.
˚
appeared in the checkCIF procedure (http://journals.iucr.org/
services/cif/checking/checkfull.html) due to large values of
ADP max/min ratios, especially on atoms C52 (ratio = 4.2) and
C55 (ratio = 3.5). Introduction of rigid-bond restraints applied
to the C51–C55 atoms in the refinement led to a decrease in
the ADP max/min ratios (4.0 and 3.2, respectively) and
provided more realistic anisotropic atomic displacements on
this cyclopentadienyl (Cp) ring. No constraints were used to
refine the other rings.
A and B (Fig. 4, top right; r.m.s. deviation of 2.09 A) and the
˚
molecules B and C (Fig. 4, top left; r.m.s. deviation of 2.17 A).
A packing similarity search (using the Mercury Solid Form
module, with 20% distance tolerance, 20ꢀ angle tolerance, H-
atom position and bond type ignored, structure inversion
allowed) revealed one hit between the known orthorhombic
polymorph (1A) and the anhydride molecules containing the
Fe1 and Fe2 atoms (molecule A) of the new monoclinic
polymorph (1B). Indeed, as shown in Fig. 4, a moderate
˚
overlap can be seen, with an r.m.s. deviation of 0.62 A.
Fig. 4 clearly shows why an intramolecular hydrogen bond
3. Results and discussion
occurred in (1A) (C206—H206ꢄ ꢄ ꢄO1) and not in molecule A
˚
of (1B) (C2—H2ꢄ ꢄ ꢄO15); both the Hꢄ ꢄ ꢄA distances [2.56 A in
The molecular structures of the previously described ortho-
rhombic polymorph, denoted (1A) (Fig. 1, top), and the
obtained monoclinic polymorph, denoted (1B) (Fig. 1,
bottom), feature various differences and the crystallographic
data of both polymorphs are disclosed in Table 1. The crystal
packing of polymorph (1B) is shown in Fig. 2. Only one
molecule is present in the asymmetric unit of polymorph (1A),
while three independent molecules, namely A, B and C,
crystallized in the asymmetric unit of polymorph (1B). It can
ꢀ
˚
(1A) and 3.34 A in (1B)] and the D—Hꢄ ꢄ ꢄA angles [148.9 in
(1A) and 140.9ꢀ in (1B)] are more favourable for developing
these weak interactions in (1A). In addition to this intra-
molecular hydrogen bond, three intermolecular [C205—
H205ꢄ ꢄ ꢄO2v, C204—H204ꢄ ꢄ ꢄO1vi and C207—H207ꢄ ꢄ ꢄO2vii;
symmetry codes: (v) x + 1, ꢂy, ꢂz + 1; (vi) x + 12, ꢂy + 21, ꢂz + 1;
(vii) ꢂx + 12, y + 12, z] contacts, supporting the zigzag chains of
molecules along the a axis, were observed in polymorph (1A).
Table 3
Comparison of selected geometric parameters (ꢀ) of Cp-based carboxylic anhydrides.
Compound
Anhydride torsion angle
Fc/Fc torsion angle
Cp/Cp eclipse angle
Cp/Cp planes angle
O—Cꢄ ꢄ ꢄC—C pseudo-torsion angle
(1A)
(2)
(2)
(3)
(4)
(5)
57.4 (2)
ꢂ62.4 (5)
66.7 (5)
57.0 (2)
62.3 (3)
72.2
75.1
103.7
85.9
72.9
1.5
33.6
146.3
30.1
6.3–5.3
*
*
18.9–7.0
12.8–3.2
0.6–0.4
7.3–2.5
17.1–0.7
3.9–6.2
2.84–1.75
1.96–2.52
2.61–2.71
2.31–4.55
2.19–2.03
2.51–2.51
1.33–1.72
0.89–2.51
0.39–2.22
12.1 (3)–2.1 (3)
11.7 (9)–6.2 (9)
9.8 (9)–6.2 (9)
0.7 (4)–19.4 (5)
3.6 (5)–4.2 (5)
8.3 (4)–21.7 (4)
16 (1)–1 (1)
ꢂ27.5 (2)
(1B) (molecule A) ꢂ51.0 (7)
(1B) (molecule B)
46.6 (7)
14 (1)–7 (1)
2 (1)–16 (1)
(1B) (molecule C) ꢂ46.9 (7)
Note: (*) not applicable.
ꢁ
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Figure 3
(Top right) Overlay of the molecules containing atoms Fe3/Fe4 (light grey) and Fe5/Fe6 (light blue). (Top left) Overlay of the molecules containing
atoms Fe1/Fe2 (light purple) and Fe3/Fe4 (light grey). (Bottom) Overlay of the molecules containing atoms Fe1/Fe2 (light purple) and Fe5/Fe6 (light
blue).
In (1B), although no traditional hydrogen-bond donors are
present, each carbonyl group can act as a weak hydrogen-bond
acceptor (Steiner, 2002; Desiraju, 2011). Although the zigzag
chains that are present in (1A) could not be seen in (1B), we
identified a set of weak hydrogen bonds in the latter (Table 2).
Along the b and c axes, four hydrogen bonds structure the
packing (C85—H85ꢄ ꢄ ꢄO42ii, C49—H49ꢄ ꢄ ꢄO72, C31—
H31ꢄ ꢄ ꢄO12 and C5—H5ꢄ ꢄ ꢄO45i; see Table 2 for symmetry
codes and hydrogen-bond geometry), whereas three other
hydrogen bonds (C6—H6ꢄ ꢄ ꢄO15iii, C39—H39ꢄ ꢄ ꢄO45iii and
C69—H69ꢄ ꢄ ꢄO75iv; Table 2) link molecules along the a axis
(Fig. 5).
for which a solid-state structure has been reported (see
Scheme 2): trovacenecarboxylic anhydride [(2); Elschenbroich
et al., 1997; Cambridge Structural Database (CSD; Groom et
al., 2016) refcode NEWFIE], 1,10-[(tert-butoxycarbon-
yl)amino]ferrocenecarboxylic anhydride [(3); Siebler et al.,
2010; KAJBUU], ruthenocenecarboxylic anhydride [(4);
Micallef et al., 2011; IVOYOI] and a ferrocenecyclophane [(5);
Liu et al., 2015; HOVYEY]. Our goal was therefore to see if
the structure of (1B) was closer to the free-rotating anhydrides
(2) and (4) or to the geometrically restrained ones, i.e. (3) (due
to the presence of a hydrogen bond between the two tert-
butoxycarbonyl groups) and (5) (a cyclophane structure).
It is difficult to assess if the large Fc–Fc pseudo-torsion
angle (146.2ꢀ), which places the two ferrocene moieties on
opposite sides of the anhydride group in molecule B of (1B), is
the result or the origin of the C31—H31ꢄ ꢄ ꢄO12 hydrogen
bond. Therefore, to get more information on this large
pseudo-torsion angle, we also compared new polymorph (1B)
to the five other examples of Cp-based carboxylic anhydrides
In polymorph (1B), the pseudo-torsion angles measured for
the three anhydride molecules (O12—C11ꢄ ꢄ ꢄC14—O15,
O42—C41ꢄ ꢄ ꢄC44—O45 and O72—C71ꢄ ꢄ ꢄC74—O75) are
lower than those observed for the free-rotating anhydrides, i.e.
(1A), (2) and (4) (Table 3). Furthermore, the torsion angles
between the two ferrocenyl cores of each anhydride molecule
of (1B) are outside the usual range of values. This suggests that
polymorph (1B) is closer to the geometrically restrained
metallocene anhydrides than to polymorph (1A).
Figure 4
Overlay of orthorhombic polymorph (1A) (light blue) and molecule A of
monoclinic polymorph (1B) (black and grey). H atoms have been omitted
for clarity.
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764 Tazi et al. [Fe2(C5H5)2(C12H8O3)]
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Figure 5
Chains of molecules of monoclinic polymorph (1B) along the a axis, showing the hydrogen bonds as dashed red lines. H atoms not involved in hydrogen
bonds have been omitted for clarity. Generic atom labels without symmetry codes have been used.
Intramolecular dihedral angles between the Cp rings are in
good agreement with those observed for the other derivatives.
However, the two Cp rings of one ferrocenyl core of molecule
B of (1B) are clearly eclipsed, with a C40—Cg3bꢄ ꢄ ꢄCg3a—C35
pseudo-torsion angle of 17.1ꢀ (Cg3a is the centroid of the C31–
C35 ring and Cg3b is the centroid of the C36–C40 ring). This
results from the C31—H31ꢄ ꢄ ꢄO12 hydrogen bond, which
mimics the interactions observed in 1,10-disubstituted ferro-
cene-based anhydride (3) (Scheme 2). For all six ferrocenyl
cores, the dihedral angles between Cp ring planes are within
the expected range of values, indicating the almost coplanarity
of the Cp rings.
this higher strain in (1B) might have an effect on the ther-
modynamic stability of the polymorph.
Indeed, the density rule introduced by Burger
&
Ramberger (1979a,b) states that, at absolute zero, the most
stable polymorph will have the highest density. However, the
density difference between polymorphs (1A) and (1B) (1.661
and 1.667 Mg mꢂ3, respectively) is too small to be able to
apply this rule. Therefore, it appears difficult to state clearly
which of the polymorphs is the more stable, although the
lower melting point of (1B) (386–389 K) when compared to
(1A) (413–414 K) suggests a higher stability for orthorhombic
polymorph (1A).
The angles between each carbonyl group and their respec-
tive Cp ring were finally compared. A comparison of the
torsion angles of compounds (1A)–(5) clearly shows that, as
the geometry is constrained [intramolecular hydrogen
bonding in (3) and a cyclophane structure in (5)], high values
are observed [19.4ꢀ in (3) and 21.7ꢀ in (5)]. Such a torsion
might be viewed as another mechanism to relieve steric strain.
The torsion angles measured for the three molecules that
crystallize in (1B) are between those of the unconstrained
anhydrides [(1A), (2) and (4)] and those of the constrained
anhydrides [(3) and (5)]. Accordingly, this suggests that steric
strain exists to a higher degree in the new monoclinic poly-
morph, when compared to the orthorhombic one. Therefore,
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Hoffmann, K., Riesselmann, B. & Wenzel, M. (1980). Liebigs Ann.
Chem. pp. 1181–1185.
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Liu, Y., Khalili Najafabadi, B., Azizpoor Fard, M. & Corrigan, J. F.
(2015). Angew. Chem. Int. Ed. 54, 4832–4835.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe,
P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. &
Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.
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M. L. (2011). Organometallics, 30, 1395–1403.
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V., Jouikov, V., Radha Krishna, P. & Mongin, F. (2016). New. J.
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98.
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1480.
Sheldrick, G. M. (2014). SADABS. Bruker AXS Inc., Madison,
Wisconsin, USA.
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
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ꢁ
766 Tazi et al. [Fe2(C5H5)2(C12H8O3)]
Acta Cryst. (2017). C73, 760–766

supporting information
supporting information
Acta Cryst. (2017). C73, 760-766 [https://doi.org/10.1107/S205322961701124X]
Ferrocenecarboxylic anhydride: identification of a new polymorph
Mehdi Tazi, Thierry Roisnel, Florence Mongin and William Erb
Computing details
Data collection: APEX2 (Bruker, 2014); cell refinement: APEX2 (Bruker, 2014); data reduction: APEX2 (Bruker, 2014);
program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016
(Sheldrick, 2015b); molecular graphics: SXGRAPH (Farrugia, 1999) and Mercury (Macrae et al., 2008); software used to
prepare material for publication: CRYSCALC (T. Roisnel, local program).
Ferrocenecarboxylic anhydride
Crystal data
[Fe2(C5H5)2(C12H8O3)]
Mr = 442.06
F(000) = 2712
Dx = 1.661 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 9522 reflections
θ = 2.2–27.5°
Monoclinic, Cc
a = 5.9758 (5) Å
b = 36.456 (3) Å
c = 24.363 (2) Å
β = 91.997 (3)°
V = 5304.4 (8) Å3
Z = 12
µ = 1.66 mm−1
T = 150 K
Prism, red
0.56 × 0.36 × 0.30 mm
Data collection
Bruker APEXII
diffractometer
Radiation source: fine-focus sealed tube
Graphite monochromator
16323 measured reflections
10804 independent reflections
10350 reflections with I > 2σ(I)
Rint = 0.023
CCD rotation images, thin slices scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 2014)
θmax = 27.5°, θmin = 3.4°
h = −6→7
k = −46→41
l = −31→31
T
min = 0.466, Tmax = 0.608
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.049
wR(F2) = 0.119
S = 1.11
10804 reflections
731 parameters
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0346P)2 + 44.5361P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.004
Δρmax = 0.97 e Å−3
Δρmin = −0.86 e Å−3
Absolute structure: Refined as an inversion
twin.
32 restraints
Hydrogen site location: inferred from
neighbouring sites
Absolute structure parameter: 0.21 (3)
Acta Cryst. (2017). C73, 760-766
sup-1

supporting information
Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance
matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles;
correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate
(isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.
The crystal structure was solved in the noncentrosymmetric Cc space group by a dual-space algorithm using the SHELXT
program (Sheldrick, 2015a), and then refined with full-matrix least-square methods based on F2 (SHELXL) (Sheldrick,
2015). The use of combined TWIN and BASF instructions led to a Flack parameter value of 0.21 (3), corresponding to a
mixture of ~80% of a particular enantiomer and ~20% of the opposite one. All non-hydrogen atoms were refined with
anisotropic atomic displacement parameters.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
Fe1
Fe2
C1
H1
C2
H2
C3
H3
C4
H4
C5
H5
C6
H6
C7
H7
C8
0.66892 (17)
0.77528 (18)
0.9175 (15)
1.039804
0.9157 (18)
1.035337
0.6988 (17)
0.647300
0.5740 (17)
0.424257
0.7093 (16)
0.667352
0.4810 (14)
0.414618
0.3812 (15)
0.235063
0.5414 (16)
0.516861
0.25136 (3)
0.42693 (3)
0.2316 (3)
0.217048
0.2706 (3)
0.286714
0.2808 (3)
0.305184
0.2487 (3)
0.247739
0.2178 (2)
0.192733
0.2821 (2)
0.305163
0.2473 (3)
0.242825
0.2194 (2)
0.193681
0.87909 (4)
0.87935 (4)
0.9297 (3)
0.918481
0.9328 (4)
0.924791
0.9502 (3)
0.955372
0.9584 (3)
0.970202
0.9460 (3)
0.948327
0.8246 (3)
0.831903
0.8311 (4)
0.843789
0.8151 (3)
0.814855
0.8001 (3)
0.788635
0.8050 (3)
0.7922 (3)
0.7668 (2)
0.8093 (3)
0.8213 (3)
0.8384 (3)
0.8148 (3)
0.8294 (3)
0.840479
0.8240 (4)
0.830804
0.0139 (2)
0.0148 (2)
0.0214 (18)
0.026*
0.027 (2)
0.033*
0.026 (2)
0.031*
0.029 (2)
0.034*
0.0210 (18)
0.025*
0.0200 (17)
0.024*
0.0233 (19)
0.028*
0.0219 (19)
0.026*
H8
C9
H9
0.7366 (14)
0.869574
0.2372 (2)
0.225587
0.0162 (16)
0.019*
C10
C11
O12
O13
C14
O15
C16
C17
H17
C18
H18
0.7016 (14)
0.8735 (14)
1.0359 (10)
0.8141 (10)
0.9835 (14)
1.1652 (11)
0.9037 (14)
1.0423 (15)
1.196212
0.2760 (2)
0.3030 (2)
0.29726 (16)
0.33825 (15)
0.3631 (2)
0.35399 (18)
0.4008 (2)
0.4320 (2)
0.431470
0.0160 (16)
0.0163 (16)
0.0207 (12)
0.0216 (13)
0.0194 (17)
0.0303 (15)
0.0171 (16)
0.0195 (17)
0.023*
0.9051 (17)
0.951423
0.4634 (2)
0.487904
0.0243 (19)
0.029*
Acta Cryst. (2017). C73, 760-766
sup-2

supporting information
C19
H19
C20
H20
C21
H21
C22
H22
C23
H23
C24
H24
C25
H25
Fe3
0.6851 (17)
0.560381
0.6853 (17)
0.560855
0.7724 (19)
0.828477
0.8980 (18)
1.050631
0.752 (2)
0.789798
0.5450 (18)
0.417618
0.5506 (17)
0.428828
0.46792 (17)
0.57218 (18)
0.7070 (15)
0.828758
0.4891 (15)
0.439045
0.3616 (16)
0.210327
0.4936 (16)
0.447131
0.7096 (15)
0.833920
0.5523 (15)
0.692169
0.3663 (15)
0.360217
0.1900 (14)
0.047410
0.4521 (3)
0.467834
0.4136 (2)
0.398800
0.3908 (3)
0.366436
0.4225 (3)
0.423019
0.4529 (3)
0.477726
0.4402 (3)
0.455136
0.4018 (3)
0.386282
0.31132 (3)
0.40600 (3)
0.2726 (2)
0.275326
0.2595 (2)
0.252074
0.2594 (2)
0.251498
0.2728 (2)
0.275964
0.2808 (2)
0.289969
0.3609 (2)
0.367472
0.3455 (2)
0.339898
0.3400 (2)
0.329689
0.3525 (2)
0.352853
0.3646 (2)
0.3784 (2)
0.39414 (16)
0.37180 (16)
0.3607 (2)
0.3501 (2)
0.3618 (2)
0.3536 (2)
0.346446
0.3582 (2)
0.354949
0.3686 (2)
0.373221
0.3708 (2)
0.8065 (3)
0.799703
0.8010 (3)
0.789867
0.9427 (4)
0.940963
0.9591 (4)
0.971281
0.9536 (4)
0.961346
0.9351 (4)
0.927400
0.9295 (4)
0.918833
0.63680 (4)
0.37638 (5)
0.6569 (4)
0.682749
0.6684 (4)
0.703295
0.6191 (4)
0.614924
0.5763 (4)
0.538900
0.6001 (4)
0.581125
0.6721 (3)
0.689055
0.6989 (3)
0.736940
0.6585 (3)
0.665007
0.6073 (3)
0.573779
0.6147 (3)
0.5741 (3)
0.5815 (2)
0.5205 (2)
0.4809 (3)
0.4903 (3)
0.4260 (3)
0.3771 (3)
0.375178
0.3315 (3)
0.293870
0.3535 (3)
0.332550
0.4115 (3)
0.025 (2)
0.030*
0.0223 (19)
0.027*
0.030 (2)
0.036*
0.029 (2)
0.035*
0.034 (2)
0.040*
0.032 (2)
0.038*
0.030 (2)
0.036*
0.0133 (2)
0.0153 (2)
0.0227 (18)
0.027*
0.0200 (18)
0.024*
0.028 (2)
0.033*
0.026 (2)
0.031*
0.0207 (17)
0.025*
0.0164 (16)
0.020*
0.0190 (17)
0.023*
0.0187 (17)
0.022*
0.0168 (16)
0.020*
Fe4
C31
H31
C32
H32
C33
H33
C34
H34
C35
H35
C36
H36
C37
H37
C38
H38
C39
H39
C40
C41
O42
O43
C44
O45
C46
C47
H47
C48
H48
C49
H49
C50
0.2629 (13)
0.176542
0.4903 (14)
0.6414 (14)
0.8139 (10)
0.5497 (9)
0.6920 (14)
0.8791 (11)
0.5811 (14)
0.6960 (15)
0.848402
0.5422 (16)
0.573395
0.3297 (15)
0.195696
0.0164 (16)
0.0160 (16)
0.0215 (12)
0.0189 (12)
0.0194 (17)
0.0338 (16)
0.0153 (16)
0.0194 (17)
0.023*
0.0220 (18)
0.026*
0.0210 (17)
0.025*
0.3544 (15)
0.0184 (16)
Acta Cryst. (2017). C73, 760-766
sup-3

supporting information
H50
C51
H51
C52
H52
C53
H53
C54
H54
C55
H55
Fe5
0.240895
0.728 (2)
0.793885
0.8335 (18)
0.985347
0.6819 (17)
0.711729
0.4798 (17)
0.345905
0.5060 (19)
0.393324
0.33502 (18)
0.23842 (17)
0.0970 (16)
−0.020313
0.0845 (17)
−0.041795
0.2935 (19)
0.331205
0.4396 (16)
0.590584
0.3134 (17)
0.366259
0.2658 (15)
0.133989
0.4667 (17)
0.492792
0.6207 (14)
0.768288
0.5190 (14)
0.585670
0.3006 (14)
0.1346 (14)
−0.0277 (10)
0.1944 (10)
0.0267 (14)
−0.1612 (12)
0.1159 (15)
−0.0157 (15)
−0.170876
0.1250 (16)
0.082088
0.3462 (16)
0.475060
0.3403 (15)
0.463734
0.2521 (17)
0.217517
0.377115
0.4484 (3)
0.447590
0.4405 (2)
0.433211
0.4449 (2)
0.441280
0.4557 (2)
0.460706
0.4578 (2)
0.464499
0.34823 (3)
0.51994 (3)
0.3689 (3)
0.385284
0.3301 (3)
0.315850
0.3165 (3)
0.291237
0.3463 (3)
0.344801
0.3792 (3)
0.403640
0.3323 (2)
0.320192
0.3153 (2)
0.289689
0.3432 (2)
0.339305
0.3778 (2)
0.401011
0.3715 (2)
0.3983 (2)
0.39262 (16)
0.43342 (15)
0.4584 (2)
0.45021 (19)
0.4959 (2)
0.5279 (2)
0.527999
0.5585 (2)
0.583140
0.5462 (2)
0.561280
0.5079 (2)
0.492840
0.5454 (3)
0.570329
0.436107
0.4167 (5)
0.452753
0.3678 (5)
0.365214
0.3231 (4)
0.285409
0.3444 (4)
0.323581
0.4023 (4)
0.427024
0.12474 (4)
0.12024 (5)
0.0707 (4)
0.079396
0.0715 (4)
0.080788
0.0559 (4)
0.052840
0.0456 (3)
0.034772
0.0547 (4)
0.050703
0.2028 (3)
0.213829
0.1860 (3)
0.183871
0.1732 (4)
0.161118
0.1813 (3)
0.175416
0.1998 (3)
0.2153 (3)
0.2416 (2)
0.1985 (3)
0.1851 (3)
0.1717 (3)
0.1878 (3)
0.1725 (4)
0.162638
0.1748 (4)
0.167108
0.1907 (4)
0.195172
0.1987 (3)
0.209522
0.0460 (4)
0.038538
0.022*
0.041 (3)
0.050*
0.040 (2)
0.048*
0.030 (2)
0.036*
0.029 (2)
0.035*
0.033 (2)
0.039*
0.0149 (2)
0.0141 (2)
0.027 (2)
0.032*
0.027 (2)
0.033*
0.029 (2)
0.035*
0.0232 (19)
0.028*
0.025 (2)
0.030*
0.0185 (17)
0.022*
0.0232 (19)
0.028*
0.0194 (17)
0.023*
0.0165 (16)
0.020*
0.0146 (16)
0.0168 (16)
0.0227 (13)
0.0213 (13)
0.0178 (17)
0.0355 (17)
0.0193 (18)
0.0203 (17)
0.024*
0.0243 (19)
0.029*
0.0224 (19)
0.027*
Fe6
C61
H61
C62
H62
C63
H63
C64
H64
C65
H65
C66
H66
C67
H67
C68
H68
C69
H69
C70
C71
O72
O73
C74
O75
C76
C77
H77
C78
H78
C79
H79
C80
H80
C81
H81
0.0204 (18)
0.024*
0.0248 (19)
0.030*
Acta Cryst. (2017). C73, 760-766
sup-4

supporting information
C82
H82
C83
H83
C84
H84
C85
H85
0.0982 (16)
−0.056804
0.2177 (18)
0.155211
0.4430 (17)
0.558431
0.5157 (3)
0.517241
0.4835 (3)
0.459554
0.4923 (3)
0.475531
0.5313 (3)
0.545007
0.0433 (4)
0.033535
0.0577 (4)
0.059395
0.0691 (4)
0.079604
0.0619 (4)
0.066879
0.028 (2)
0.034*
0.028 (2)
0.034*
0.028 (2)
0.033*
0.026 (2)
0.032*
0.4681 (17)
0.602464
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
Fe1
Fe2
C1
C2
C3
C4
C5
C6
C7
0.0178 (6)
0.0194 (6)
0.022 (4)
0.036 (5)
0.040 (6)
0.030 (5)
0.034 (5)
0.015 (4)
0.019 (4)
0.032 (5)
0.022 (4)
0.021 (4)
0.024 (4)
0.022 (3)
0.018 (3)
0.019 (4)
0.024 (4)
0.023 (4)
0.020 (4)
0.036 (5)
0.037 (5)
0.033 (5)
0.045 (6)
0.039 (6)
0.054 (7)
0.038 (6)
0.029 (5)
0.0150 (5)
0.0190 (6)
0.026 (5)
0.028 (5)
0.027 (5)
0.028 (5)
0.021 (4)
0.024 (4)
0.031 (5)
0.0130 (5)
0.0126 (5)
0.025 (5)
0.024 (5)
0.021 (4)
0.043 (6)
0.018 (4)
0.028 (5)
0.033 (5)
0.018 (4)
0.020 (4)
0.016 (4)
0.012 (4)
0.020 (3)
0.014 (3)
0.021 (4)
0.023 (3)
0.014 (4)
0.022 (4)
0.017 (4)
0.027 (5)
0.017 (4)
0.028 (5)
0.031 (5)
0.031 (5)
0.044 (6)
0.039 (6)
0.0121 (5)
0.0115 (5)
0.018 (4)
0.008 (4)
0.011 (4)
0.025 (5)
0.016 (4)
0.013 (4)
0.013 (4)
0.0110 (5)
0.0014 (4)
0.0006 (5)
0.004 (4)
0.001 (4)
0.003 (4)
0.001 (4)
0.002 (4)
0.003 (3)
−0.006 (4)
−0.009 (4)
0.003 (3)
−0.006 (3)
0.000 (3)
−0.001 (2)
0.001 (2)
0.000 (3)
0.004 (3)
0.002 (3)
−0.008 (3)
−0.009 (4)
0.011 (4)
0.007 (4)
−0.004 (4)
−0.001 (4)
−0.006 (5)
0.014 (5)
−0.013 (4)
0.0012 (4)
−0.0025 (4)
0.008 (3)
0.004 (3)
−0.002 (3)
0.006 (4)
0.005 (3)
0.004 (3)
0.002 (3)
0.0012 (4)
−0.0034 (4)
−0.002 (3)
−0.007 (4)
0.001 (4)
0.007 (4)
0.002 (3)
−0.002 (3)
0.002 (3)
−0.002 (4)
0.002 (3)
0.001 (3)
0.000 (3)
0.003 (2)
0.001 (3)
−0.003 (3)
−0.013 (3)
0.002 (3)
0.002 (3)
0.001 (4)
−0.005 (4)
−0.007 (4)
0.004 (4)
−0.005 (4)
−0.003 (4)
0.005 (4)
0.005 (4)
−0.0014 (4)
0.0014 (4)
−0.011 (4)
−0.006 (4)
−0.011 (4)
−0.005 (4)
0.002 (3)
−0.001 (3)
0.002 (3)
0.0008 (4)
−0.0006 (4)
0.007 (3)
0.000 (4)
−0.007 (3)
−0.002 (4)
0.004 (3)
0.003 (3)
0.008 (4)
0.003 (3)
0.000 (3)
0.001 (3)
0.002 (3)
−0.002 (2)
−0.002 (2)
−0.009 (3)
−0.010 (3)
−0.005 (3)
0.000 (3)
0.005 (3)
0.005 (3)
−0.007 (3)
0.008 (4)
0.001 (4)
−0.011 (4)
−0.002 (4)
−0.003 (4)
−0.0003 (4)
0.0001 (4)
−0.007 (3)
0.003 (3)
−0.001 (4)
−0.005 (4)
0.000 (3)
−0.005 (3)
0.001 (3)
0.0123 (5)
0.017 (4)
0.021 (4)
0.016 (4)
0.014 (4)
0.011 (4)
0.017 (4)
0.018 (4)
0.016 (4)
0.007 (3)
0.011 (3)
0.013 (4)
0.020 (3)
0.032 (3)
0.017 (4)
0.043 (4)
0.015 (4)
0.017 (4)
0.020 (4)
0.010 (4)
0.016 (4)
0.018 (4)
0.016 (4)
0.016 (4)
0.013 (4)
0.022 (4)
0.0125 (5)
0.0153 (5)
0.023 (4)
0.024 (4)
0.044 (6)
0.023 (4)
0.025 (4)
0.013 (3)
0.013 (4)
C8
C9
C10
C11
O12
O13
C14
O15
C16
C17
C18
C19
C20
C21
C22
C23
C24
C25
Fe3
Fe4
C31
C32
C33
C34
C35
C36
C37
Acta Cryst. (2017). C73, 760-766
sup-5

supporting information
C38
C39
C40
C41
O42
O43
C44
O45
C46
C47
C48
C49
C50
C51
C52
C53
C54
C55
Fe5
0.022 (4)
0.010 (4)
0.015 (4)
0.018 (4)
0.019 (3)
0.016 (3)
0.023 (4)
0.029 (4)
0.019 (4)
0.025 (4)
0.037 (5)
0.020 (4)
0.022 (4)
0.060 (7)
0.031 (5)
0.042 (5)
0.028 (5)
0.053 (6)
0.0181 (6)
0.0159 (5)
0.022 (5)
0.028 (5)
0.047 (6)
0.027 (5)
0.036 (5)
0.025 (5)
0.038 (5)
0.015 (4)
0.021 (4)
0.020 (4)
0.021 (4)
0.022 (3)
0.019 (3)
0.016 (4)
0.027 (4)
0.028 (5)
0.020 (4)
0.034 (5)
0.029 (5)
0.021 (4)
0.034 (5)
0.022 (5)
0.039 (6)
0.032 (5)
0.027 (5)
0.017 (4)
0.021 (4)
0.024 (4)
0.019 (4)
0.023 (3)
0.029 (3)
0.021 (4)
0.050 (4)
0.009 (3)
0.010 (3)
0.014 (4)
0.021 (4)
0.013 (4)
0.021 (5)
0.013 (4)
0.014 (4)
0.020 (4)
0.007 (4)
0.0135 (5)
0.0120 (5)
0.036 (5)
0.036 (5)
0.022 (5)
0.033 (5)
0.022 (5)
0.014 (4)
0.016 (4)
0.019 (4)
0.011 (4)
0.011 (4)
0.016 (4)
0.024 (3)
0.010 (3)
0.017 (4)
0.028 (4)
0.021 (4)
0.016 (4)
0.018 (4)
0.020 (4)
0.024 (5)
0.024 (5)
0.045 (6)
0.022 (5)
0.024 (5)
0.030 (5)
0.018 (4)
0.020 (4)
0.010 (3)
0.011 (3)
0.023 (3)
0.012 (3)
0.015 (4)
0.022 (3)
0.018 (4)
0.023 (4)
0.015 (4)
0.022 (4)
0.020 (4)
0.042 (5)
0.076 (7)
0.035 (5)
0.040 (5)
0.039 (5)
0.0133 (5)
0.0143 (5)
0.023 (4)
0.018 (4)
0.018 (4)
0.010 (4)
0.017 (4)
0.017 (4)
0.016 (4)
0.024 (4)
0.017 (4)
0.013 (3)
0.014 (3)
0.022 (3)
0.035 (3)
0.020 (4)
0.050 (4)
0.009 (3)
0.025 (4)
0.021 (4)
0.018 (4)
0.015 (4)
0.017 (4)
0.017 (4)
0.023 (4)
0.027 (5)
0.022 (4)
0.002 (3)
0.001 (3)
0.005 (3)
0.005 (3)
−0.005 (2)
0.001 (2)
0.008 (3)
0.024 (3)
0.003 (3)
−0.002 (3)
−0.006 (4)
−0.008 (3)
−0.006 (3)
−0.015 (5)
−0.012 (4)
−0.006 (4)
0.007 (4)
−0.002 (4)
−0.0010 (5)
−0.0006 (4)
0.006 (4)
−0.006 (4)
0.004 (4)
−0.004 (4)
0.003 (4)
−0.001 (3)
−0.004 (4)
0.003 (3)
−0.006 (3)
−0.003 (3)
−0.003 (3)
0.004 (2)
−0.002 (2)
−0.001 (3)
−0.010 (3)
0.003 (4)
0.008 (3)
0.005 (4)
−0.003 (4)
0.001 (3)
0.003 (4)
−0.005 (4)
−0.010 (4)
0.013 (4)
−0.005 (4)
0.014 (3)
0.003 (3)
−0.001 (3)
−0.003 (3)
0.001 (2)
0.001 (2)
0.005 (3)
0.002 (3)
0.004 (3)
0.004 (3)
0.002 (4)
−0.008 (3)
0.003 (3)
−0.015 (5)
−0.002 (5)
0.015 (4)
0.010 (4)
0.015 (4)
0.0030 (4)
−0.0026 (4)
0.003 (4)
−0.004 (4)
−0.003 (4)
0.011 (3)
0.002 (4)
0.003 (3)
0.000 (4)
0.004 (3)
0.003 (3)
0.002 (3)
−0.002 (3)
0.007 (2)
0.003 (3)
−0.001 (3)
−0.013 (3)
0.003 (3)
0.008 (4)
0.002 (4)
−0.006 (4)
−0.006 (3)
0.000 (4)
−0.005 (3)
−0.003 (4)
0.008 (4)
0.006 (4)
0.007 (3)
0.009 (3)
−0.004 (3)
0.002 (3)
0.003 (2)
0.003 (2)
0.005 (3)
−0.002 (3)
0.000 (3)
0.001 (3)
0.000 (3)
−0.001 (3)
0.000 (3)
−0.007 (4)
0.005 (4)
0.003 (4)
0.004 (4)
−0.008 (4)
0.0004 (4)
−0.0012 (4)
0.003 (4)
0.001 (4)
−0.009 (4)
−0.001 (3)
0.004 (3)
0.001 (3)
0.004 (3)
0.001 (3)
−0.001 (3)
−0.001 (3)
0.001 (3)
0.005 (2)
0.003 (2)
0.005 (3)
0.019 (3)
0.000 (3)
0.002 (3)
−0.002 (3)
−0.007 (3)
−0.001 (3)
0.002 (3)
−0.008 (4)
−0.008 (4)
0.001 (4)
−0.005 (4)
Fe6
C61
C62
C63
C64
C65
C66
C67
C68
C69
C70
C71
O72
O73
C74
O75
C76
C77
C78
C79
C80
C81
C82
C83
C84
C85
Acta Cryst. (2017). C73, 760-766
sup-6

supporting information
Geometric parameters (Å, º)
Fe1—C1
Fe1—C10
Fe1—C4
Fe1—C3
Fe1—C6
Fe1—C5
Fe1—C9
Fe1—C7
Fe1—C2
Fe1—C8
Fe2—C16
Fe2—C20
Fe2—C24
Fe2—C21
Fe2—C17
Fe2—C23
Fe2—C19
Fe2—C22
Fe2—C25
Fe2—C18
C1—C5
C1—C2
C1—H1
C2—C3
C2—H2
C3—C4
C3—H3
C4—C5
C4—H4
C5—H5
C6—C7
C6—C10
C6—H6
C7—C8
C7—H7
C8—C9
C8—H8
C9—C10
C9—H9
2.030 (9)
2.031 (8)
2.035 (9)
2.041 (8)
2.042 (8)
2.046 (8)
2.047 (7)
2.050 (9)
2.060 (10)
2.070 (9)
2.012 (8)
2.026 (8)
2.026 (10)
2.030 (9)
2.049 (9)
2.051 (9)
2.054 (8)
2.058 (9)
2.061 (10)
2.064 (9)
1.411 (13)
1.427 (13)
0.9500
1.427 (14)
0.9500
1.406 (14)
0.9500
1.424 (13)
0.9500
0.9500
1.412 (13)
1.435 (12)
0.9500
1.459 (13)
0.9500
1.393 (12)
0.9500
1.436 (11)
0.9500
C36—H36
C37—C38
C37—H37
C38—C39
C38—H38
C39—C40
C39—H39
C40—C41
C41—O42
C41—O43
O43—C44
C44—O45
C44—C46
C46—C47
C46—C50
C47—C48
C47—H47
C48—C49
C48—H48
C49—C50
C49—H49
C50—H50
C51—C52
C51—C55
C51—H51
C52—C53
C52—H52
C53—C54
C53—H53
C54—C55
C54—H54
C55—H55
Fe5—C70
Fe5—C69
Fe5—C66
Fe5—C63
Fe5—C65
Fe5—C61
Fe5—C64
Fe5—C68
Fe5—C67
Fe5—C62
Fe6—C83
Fe6—C76
Fe6—C82
Fe6—C80
0.9500
1.432 (12)
0.9500
1.411 (10)
0.9500
1.434 (11)
0.9500
1.453 (11)
1.188 (10)
1.419 (9)
1.368 (9)
1.198 (10)
1.474 (11)
1.427 (11)
1.426 (12)
1.425 (12)
0.9500
1.446 (13)
0.9500
1.416 (12)
0.9500
0.9500
1.398 (16)
1.403 (16)
0.9500
1.402 (15)
0.9500
1.387 (13)
0.9500
1.417 (14)
0.9500
0.9500
2.032 (8)
2.040 (8)
2.044 (8)
2.046 (9)
2.047 (9)
2.049 (9)
2.049 (8)
2.050 (9)
2.051 (9)
2.056 (10)
2.023 (9)
2.024 (8)
2.033 (9)
2.034 (8)
C10—C11
C11—O12
C11—O13
O13—C14
C14—O15
C14—C16
C16—C20
1.464 (11)
1.187 (10)
1.402 (9)
1.382 (10)
1.195 (10)
1.463 (11)
1.415 (12)
Acta Cryst. (2017). C73, 760-766
sup-7

supporting information
C16—C17
C17—C18
C17—H17
C18—C19
C18—H18
C19—C20
C19—H19
C20—H20
C21—C25
C21—C22
C21—H21
C22—C23
C22—H22
C23—C24
C23—H23
C24—C25
C24—H24
C25—H25
Fe3—C40
Fe3—C33
Fe3—C32
Fe3—C34
Fe3—C38
Fe3—C39
Fe3—C35
Fe3—C36
Fe3—C31
Fe3—C37
Fe4—C46
Fe4—C52
Fe4—C55
Fe4—C50
Fe4—C54
Fe4—C51
Fe4—C53
Fe4—C47
Fe4—C49
Fe4—C48
C31—C35
C31—C32
C31—H31
C32—C33
C32—H32
C33—C34
C33—H33
C34—C35
C34—H34
C35—H35
1.443 (11)
1.411 (13)
0.9500
1.428 (14)
0.9500
1.411 (12)
0.9500
0.9500
1.411 (15)
1.427 (14)
0.9500
1.414 (15)
0.9500
1.383 (16)
0.9500
1.407 (15)
0.9500
Fe6—C77
Fe6—C81
Fe6—C84
Fe6—C79
Fe6—C85
Fe6—C78
C61—C65
C61—C62
C61—H61
C62—C63
C62—H62
C63—C64
C63—H63
C64—C65
C64—H64
C65—H65
C66—C67
C66—C70
C66—H66
C67—C68
C67—H67
C68—C69
C68—H68
C69—C70
C69—H69
C70—C71
C71—O72
C71—O73
O73—C74
C74—O75
C74—C76
C76—C80
C76—C77
C77—C78
C77—H77
C78—C79
C78—H78
C79—C80
C79—H79
C80—H80
C81—C82
C81—C85
C81—H81
C82—C83
C82—H82
C83—C84
C83—H83
C84—C85
2.036 (8)
2.036 (9)
2.042 (9)
2.050 (8)
2.052 (9)
2.065 (9)
1.414 (13)
1.418 (14)
0.9500
1.408 (14)
0.9500
1.423 (14)
0.9500
1.439 (13)
0.9500
0.9500
1.423 (13)
1.446 (11)
0.9500
1.411 (12)
0.9500
0.9500
2.020 (8)
2.040 (8)
2.044 (8)
2.045 (9)
2.048 (8)
2.052 (8)
2.053 (8)
2.056 (8)
2.057 (9)
2.068 (8)
2.015 (8)
2.022 (9)
2.036 (8)
2.037 (8)
2.039 (9)
2.040 (9)
2.047 (9)
2.048 (8)
2.052 (8)
2.062 (8)
1.417 (12)
1.424 (13)
0.9500
1.417 (11)
0.9500
1.414 (11)
0.9500
1.450 (11)
1.199 (10)
1.396 (9)
1.385 (10)
1.196 (10)
1.467 (12)
1.427 (13)
1.448 (11)
1.399 (13)
0.9500
1.437 (13)
0.9500
1.408 (12)
0.9500
0.9500
1.419 (14)
1.430 (14)
0.9500
1.413 (14)
0.9500
1.402 (14)
0.9500
1.440 (13)
1.401 (12)
0.9500
1.416 (14)
0.9500
1.427 (13)
0.9500
0.9500
Acta Cryst. (2017). C73, 760-766
sup-8

supporting information
C36—C37
C36—C40
1.423 (12)
1.441 (10)
C84—H84
C85—H85
0.9500
0.9500
C1—Fe1—C10
C1—Fe1—C4
C10—Fe1—C4
C1—Fe1—C3
C10—Fe1—C3
C4—Fe1—C3
C1—Fe1—C6
C10—Fe1—C6
C4—Fe1—C6
C3—Fe1—C6
C1—Fe1—C5
C10—Fe1—C5
C4—Fe1—C5
C3—Fe1—C5
C6—Fe1—C5
C1—Fe1—C9
C10—Fe1—C9
C4—Fe1—C9
C3—Fe1—C9
C6—Fe1—C9
C5—Fe1—C9
C1—Fe1—C7
C10—Fe1—C7
C4—Fe1—C7
C3—Fe1—C7
C6—Fe1—C7
C5—Fe1—C7
C9—Fe1—C7
C1—Fe1—C2
C10—Fe1—C2
C4—Fe1—C2
C3—Fe1—C2
C6—Fe1—C2
C5—Fe1—C2
C9—Fe1—C2
C7—Fe1—C2
C1—Fe1—C8
C10—Fe1—C8
C4—Fe1—C8
C3—Fe1—C8
C6—Fe1—C8
C5—Fe1—C8
C9—Fe1—C8
C7—Fe1—C8
C2—Fe1—C8
127.3 (4)
68.2 (4)
154.6 (4)
68.3 (4)
120.9 (3)
40.4 (4)
164.5 (4)
41.3 (3)
118.5 (4)
107.0 (4)
40.5 (4)
163.7 (4)
40.9 (4)
68.5 (4)
153.2 (4)
108.5 (3)
41.2 (3)
162.1 (4)
156.5 (4)
69.5 (3)
125.2 (3)
154.4 (4)
68.3 (3)
106.3 (4)
124.6 (4)
40.4 (3)
119.0 (4)
68.6 (4)
40.8 (4)
109.0 (4)
68.3 (4)
40.7 (4)
126.2 (4)
68.7 (4)
121.5 (4)
162.5 (4)
120.0 (4)
67.8 (3)
125.5 (4)
162.6 (4)
68.8 (4)
107.1 (3)
39.6 (3)
41.5 (4)
155.0 (4)
C33—C34—Fe3
C35—C34—Fe3
C33—C34—H34
C35—C34—H34
Fe3—C34—H34
C31—C35—C34
C31—C35—Fe3
C34—C35—Fe3
C31—C35—H35
C34—C35—H35
Fe3—C35—H35
C37—C36—C40
C37—C36—Fe3
C40—C36—Fe3
C37—C36—H36
C40—C36—H36
Fe3—C36—H36
C36—C37—C38
C36—C37—Fe3
C38—C37—Fe3
C36—C37—H37
C38—C37—H37
Fe3—C37—H37
C39—C38—C37
C39—C38—Fe3
C37—C38—Fe3
C39—C38—H38
C37—C38—H38
Fe3—C38—H38
C38—C39—C40
C38—C39—Fe3
C40—C39—Fe3
C38—C39—H39
C40—C39—H39
Fe3—C39—H39
C39—C40—C36
C39—C40—C41
C36—C40—C41
C39—C40—Fe3
C36—C40—Fe3
C41—C40—Fe3
O42—C41—O43
O42—C41—C40
O43—C41—C40
C44—O43—C41
69.5 (5)
69.9 (5)
126.6
126.6
125.6
108.3 (8)
70.0 (5)
69.3 (5)
125.8
125.8
126.5
107.7 (7)
70.3 (5)
68.0 (5)
126.2
126.2
127.1
107.9 (7)
69.3 (5)
68.9 (4)
126.1
126.1
127.3
108.7 (7)
70.0 (4)
70.4 (5)
125.6
125.6
125.5
107.9 (7)
69.7 (5)
68.2 (4)
126.0
126.0
127.6
107.7 (7)
129.0 (7)
123.3 (8)
70.6 (5)
70.6 (5)
124.3 (6)
121.8 (7)
128.3 (7)
109.8 (7)
117.9 (6)
Acta Cryst. (2017). C73, 760-766
sup-9

supporting information
C16—Fe2—C20
C16—Fe2—C24
C20—Fe2—C24
C16—Fe2—C21
C20—Fe2—C21
C24—Fe2—C21
C16—Fe2—C17
C20—Fe2—C17
C24—Fe2—C17
C21—Fe2—C17
C16—Fe2—C23
C20—Fe2—C23
C24—Fe2—C23
C21—Fe2—C23
C17—Fe2—C23
C16—Fe2—C19
C20—Fe2—C19
C24—Fe2—C19
C21—Fe2—C19
C17—Fe2—C19
C23—Fe2—C19
C16—Fe2—C22
C20—Fe2—C22
C24—Fe2—C22
C21—Fe2—C22
C17—Fe2—C22
C23—Fe2—C22
C19—Fe2—C22
C16—Fe2—C25
C20—Fe2—C25
C24—Fe2—C25
C21—Fe2—C25
C17—Fe2—C25
C23—Fe2—C25
C19—Fe2—C25
C22—Fe2—C25
C16—Fe2—C18
C20—Fe2—C18
C24—Fe2—C18
C21—Fe2—C18
C17—Fe2—C18
C23—Fe2—C18
C19—Fe2—C18
C22—Fe2—C18
C25—Fe2—C18
C5—C1—C2
41.0 (4)
157.4 (4)
121.7 (4)
107.5 (4)
123.5 (4)
67.7 (4)
41.6 (3)
69.4 (4)
159.8 (4)
122.5 (4)
161.2 (4)
156.8 (4)
39.6 (4)
68.1 (4)
124.1 (4)
68.4 (4)
40.5 (3)
108.0 (4)
159.8 (4)
68.4 (4)
122.2 (4)
124.5 (4)
160.9 (4)
67.3 (4)
40.9 (4)
108.0 (4)
40.3 (4)
157.7 (4)
121.7 (4)
107.1 (4)
40.3 (4)
40.3 (4)
158.3 (4)
67.5 (4)
123.7 (4)
67.9 (4)
68.4 (4)
68.4 (4)
124.4 (4)
158.2 (4)
40.1 (4)
108.6 (4)
40.6 (4)
122.6 (4)
160.2 (4)
109.4 (8)
70.3 (5)
70.7 (5)
O45—C44—O43
O45—C44—C46
O43—C44—C46
C47—C46—C50
C47—C46—C44
C50—C46—C44
C47—C46—Fe4
C50—C46—Fe4
C44—C46—Fe4
C48—C47—C46
C48—C47—Fe4
C46—C47—Fe4
C48—C47—H47
C46—C47—H47
Fe4—C47—H47
C47—C48—C49
C47—C48—Fe4
C49—C48—Fe4
C47—C48—H48
C49—C48—H48
Fe4—C48—H48
C50—C49—C48
C50—C49—Fe4
C48—C49—Fe4
C50—C49—H49
C48—C49—H49
Fe4—C49—H49
C49—C50—C46
C49—C50—Fe4
C46—C50—Fe4
C49—C50—H50
C46—C50—H50
Fe4—C50—H50
C52—C51—C55
C52—C51—Fe4
C55—C51—Fe4
C52—C51—H51
C55—C51—H51
Fe4—C51—H51
C51—C52—C53
C51—C52—Fe4
C53—C52—Fe4
C51—C52—H52
C53—C52—H52
Fe4—C52—H52
C54—C53—C52
C54—C53—Fe4
C52—C53—Fe4
124.0 (7)
124.7 (7)
111.2 (7)
108.8 (7)
122.6 (7)
128.6 (7)
70.7 (5)
70.2 (4)
124.5 (6)
108.0 (8)
70.3 (5)
68.2 (4)
126.0
126.0
127.1
107.0 (7)
69.2 (5)
69.1 (5)
126.5
126.5
126.9
108.8 (8)
69.1 (5)
69.8 (5)
125.6
125.6
127.0
107.4 (8)
70.3 (5)
68.6 (5)
126.3
126.3
126.4
106.7 (10)
69.2 (5)
69.7 (5)
126.6
126.6
126.0
109.9 (10)
70.6 (6)
70.8 (5)
125.0
125.0
125.2
106.8 (9)
69.9 (5)
68.9 (5)
C5—C1—Fe1
C2—C1—Fe1
Acta Cryst. (2017). C73, 760-766
sup-10

supporting information
C5—C1—H1
C2—C1—H1
Fe1—C1—H1
C1—C2—C3
C1—C2—Fe1
C3—C2—Fe1
C1—C2—H2
C3—C2—H2
Fe1—C2—H2
C4—C3—C2
C4—C3—Fe1
C2—C3—Fe1
C4—C3—H3
C2—C3—H3
Fe1—C3—H3
C3—C4—C5
C3—C4—Fe1
C5—C4—Fe1
C3—C4—H4
C5—C4—H4
Fe1—C4—H4
C1—C5—C4
C1—C5—Fe1
C4—C5—Fe1
C1—C5—H5
C4—C5—H5
Fe1—C5—H5
C7—C6—C10
C7—C6—Fe1
C10—C6—Fe1
C7—C6—H6
C10—C6—H6
Fe1—C6—H6
C6—C7—C8
C6—C7—Fe1
C8—C7—Fe1
C6—C7—H7
C8—C7—H7
Fe1—C7—H7
C9—C8—C7
C9—C8—Fe1
C7—C8—Fe1
C9—C8—H8
C7—C8—H8
Fe1—C8—H8
C8—C9—C10
C8—C9—Fe1
C10—C9—Fe1
125.3
125.3
125.2
106.5 (9)
68.5 (5)
68.9 (5)
126.8
126.8
127.4
108.5 (8)
69.6 (5)
70.4 (5)
125.8
125.8
125.9
108.7 (9)
70.0 (5)
70.0 (5)
125.7
125.7
125.9
106.9 (8)
69.2 (5)
69.1 (5)
126.5
126.5
126.7
107.1 (8)
70.1 (5)
69.0 (5)
126.4
126.4
126.1
108.1 (8)
69.5 (5)
70.0 (5)
125.9
125.9
126.1
108.1 (8)
69.3 (5)
68.5 (5)
125.9
125.9
127.8
C54—C53—H53
C52—C53—H53
Fe4—C53—H53
C53—C54—C55
C53—C54—Fe4
C55—C54—Fe4
C53—C54—H54
C55—C54—H54
Fe4—C54—H54
C51—C55—C54
C51—C55—Fe4
C54—C55—Fe4
C51—C55—H55
C54—C55—H55
Fe4—C55—H55
C70—Fe5—C69
C70—Fe5—C66
C69—Fe5—C66
C70—Fe5—C63
C69—Fe5—C63
C66—Fe5—C63
C70—Fe5—C65
C69—Fe5—C65
C66—Fe5—C65
C63—Fe5—C65
C70—Fe5—C61
C69—Fe5—C61
C66—Fe5—C61
C63—Fe5—C61
C65—Fe5—C61
C70—Fe5—C64
C69—Fe5—C64
C66—Fe5—C64
C63—Fe5—C64
C65—Fe5—C64
C61—Fe5—C64
C70—Fe5—C68
C69—Fe5—C68
C66—Fe5—C68
C63—Fe5—C68
C65—Fe5—C68
C61—Fe5—C68
C64—Fe5—C68
C70—Fe5—C67
C69—Fe5—C67
C66—Fe5—C67
C63—Fe5—C67
C65—Fe5—C67
126.6
126.6
126.2
108.7 (10)
70.4 (5)
69.5 (5)
125.6
125.6
126.0
107.8 (9)
70.0 (5)
69.8 (5)
126.1
126.1
125.7
40.6 (3)
41.6 (3)
69.1 (3)
163.8 (4)
154.1 (4)
125.4 (4)
120.9 (3)
106.8 (4)
157.4 (4)
68.1 (4)
109.6 (4)
125.9 (4)
123.0 (4)
67.7 (4)
40.4 (4)
154.8 (3)
118.6 (3)
160.7 (4)
40.7 (4)
41.1 (4)
68.6 (4)
68.2 (3)
40.5 (3)
68.3 (4)
119.7 (4)
123.8 (4)
161.7 (4)
105.3 (4)
68.7 (3)
68.4 (3)
40.7 (4)
107.4 (4)
160.3 (4)
108.0 (8)
71.1 (5)
68.8 (4)
Acta Cryst. (2017). C73, 760-766
sup-11

supporting information
C8—C9—H9
C10—C9—H9
Fe1—C9—H9
C6—C10—C9
126.0
126.0
125.7
C61—Fe5—C67
C64—Fe5—C67
C68—Fe5—C67
C70—Fe5—C62
C69—Fe5—C62
C66—Fe5—C62
C63—Fe5—C62
C65—Fe5—C62
C61—Fe5—C62
C64—Fe5—C62
C68—Fe5—C62
C67—Fe5—C62
C83—Fe6—C76
C83—Fe6—C82
C76—Fe6—C82
C83—Fe6—C80
C76—Fe6—C80
C82—Fe6—C80
C83—Fe6—C77
C76—Fe6—C77
C82—Fe6—C77
C80—Fe6—C77
C83—Fe6—C81
C76—Fe6—C81
C82—Fe6—C81
C80—Fe6—C81
C77—Fe6—C81
C83—Fe6—C84
C76—Fe6—C84
C82—Fe6—C84
C80—Fe6—C84
C77—Fe6—C84
C81—Fe6—C84
C83—Fe6—C79
C76—Fe6—C79
C82—Fe6—C79
C80—Fe6—C79
C77—Fe6—C79
C81—Fe6—C79
C84—Fe6—C79
C83—Fe6—C85
C76—Fe6—C85
C82—Fe6—C85
C80—Fe6—C85
C77—Fe6—C85
C81—Fe6—C85
C84—Fe6—C85
C79—Fe6—C85
157.5 (4)
122.9 (4)
40.3 (3)
127.4 (4)
163.7 (4)
109.2 (4)
40.2 (4)
68.2 (4)
40.4 (4)
68.5 (4)
155.2 (4)
121.6 (4)
108.3 (4)
40.8 (4)
124.6 (4)
125.1 (4)
41.2 (4)
162.0 (4)
122.5 (4)
41.8 (3)
107.2 (4)
69.4 (4)
68.5 (4)
161.1 (4)
40.8 (4)
155.9 (4)
123.0 (4)
40.4 (4)
121.6 (4)
68.6 (4)
107.6 (4)
158.0 (4)
68.8 (4)
161.3 (4)
68.5 (4)
156.3 (4)
40.3 (3)
68.2 (4)
120.7 (4)
124.4 (4)
68.6 (4)
156.9 (4)
69.0 (4)
120.6 (4)
159.4 (4)
41.0 (4)
41.2 (4)
106.7 (4)
108.6 (7)
128.7 (8)
122.6 (8)
69.8 (5)
70.0 (4)
125.1 (6)
122.4 (7)
125.8 (7)
111.5 (7)
118.2 (6)
122.7 (8)
126.0 (8)
111.1 (7)
108.5 (7)
129.0 (8)
122.1 (8)
70.0 (5)
70.5 (5)
119.5 (6)
106.8 (8)
70.5 (5)
67.8 (4)
126.6
126.6
126.6
108.7 (8)
69.4 (5)
69.4 (5)
125.6
125.6
127.2
108.1 (8)
68.7 (5)
70.1 (5)
126.0
C6—C10—C11
C9—C10—C11
C6—C10—Fe1
C9—C10—Fe1
C11—C10—Fe1
O12—C11—O13
O12—C11—C10
O13—C11—C10
C14—O13—C11
O15—C14—O13
O15—C14—C16
O13—C14—C16
C20—C16—C17
C20—C16—C14
C17—C16—C14
C20—C16—Fe2
C17—C16—Fe2
C14—C16—Fe2
C18—C17—C16
C18—C17—Fe2
C16—C17—Fe2
C18—C17—H17
C16—C17—H17
Fe2—C17—H17
C17—C18—C19
C17—C18—Fe2
C19—C18—Fe2
C17—C18—H18
C19—C18—H18
Fe2—C18—H18
C20—C19—C18
C20—C19—Fe2
C18—C19—Fe2
C20—C19—H19
C18—C19—H19
Fe2—C19—H19
C19—C20—C16
C19—C20—Fe2
C16—C20—Fe2
C19—C20—H20
C16—C20—H20
Fe2—C20—H20
C25—C21—C22
C25—C21—Fe2
126.0
126.9
108.0 (8)
70.9 (5)
69.0 (5)
126.0
126.0
125.7
108.3 (9)
71.0 (6)
Acta Cryst. (2017). C73, 760-766
sup-12

supporting information
C22—C21—Fe2
C25—C21—H21
C22—C21—H21
Fe2—C21—H21
C23—C22—C21
C23—C22—Fe2
C21—C22—Fe2
C23—C22—H22
C21—C22—H22
Fe2—C22—H22
C24—C23—C22
C24—C23—Fe2
C22—C23—Fe2
C24—C23—H23
C22—C23—H23
Fe2—C23—H23
C23—C24—C25
C23—C24—Fe2
C25—C24—Fe2
C23—C24—H24
C25—C24—H24
Fe2—C24—H24
C24—C25—C21
C24—C25—Fe2
C21—C25—Fe2
C24—C25—H25
C21—C25—H25
Fe2—C25—H25
C40—Fe3—C33
C40—Fe3—C32
C33—Fe3—C32
C40—Fe3—C34
C33—Fe3—C34
C32—Fe3—C34
C40—Fe3—C38
C33—Fe3—C38
C32—Fe3—C38
C34—Fe3—C38
C40—Fe3—C39
C33—Fe3—C39
C32—Fe3—C39
C34—Fe3—C39
C38—Fe3—C39
C40—Fe3—C35
C33—Fe3—C35
C32—Fe3—C35
C34—Fe3—C35
C38—Fe3—C35
70.6 (5)
125.8
125.8
C83—Fe6—C78
C76—Fe6—C78
C82—Fe6—C78
C80—Fe6—C78
C77—Fe6—C78
C81—Fe6—C78
C84—Fe6—C78
C79—Fe6—C78
C85—Fe6—C78
C65—C61—C62
C65—C61—Fe5
C62—C61—Fe5
C65—C61—H61
C62—C61—H61
Fe5—C61—H61
C63—C62—C61
C63—C62—Fe5
C61—C62—Fe5
C63—C62—H62
C61—C62—H62
Fe5—C62—H62
C62—C63—C64
C62—C63—Fe5
C64—C63—Fe5
C62—C63—H63
C64—C63—H63
Fe5—C63—H63
C63—C64—C65
C63—C64—Fe5
C65—C64—Fe5
C63—C64—H64
C65—C64—H64
Fe5—C64—H64
C61—C65—C64
C61—C65—Fe5
C64—C65—Fe5
C61—C65—H65
C64—C65—H65
Fe5—C65—H65
C67—C66—C70
C67—C66—Fe5
C70—C66—Fe5
C67—C66—H66
C70—C66—H66
Fe5—C66—H66
C68—C67—C66
C68—C67—Fe5
C66—C67—Fe5
156.8 (4)
68.7 (3)
120.7 (4)
68.7 (4)
39.9 (4)
106.6 (4)
161.0 (4)
40.9 (4)
123.4 (4)
108.6 (8)
69.7 (5)
70.1 (5)
125.7
125.7
126.1
107.5 (9)
69.5 (5)
69.5 (5)
126.2
126.2
126.3
109.5 (9)
70.3 (5)
69.8 (5)
125.3
125.3
126.2
106.4 (8)
69.5 (5)
69.4 (5)
126.8
126.8
125.9
108.1 (8)
69.9 (5)
69.5 (5)
126.0
126.0
126.2
106.9 (8)
69.9 (5)
68.8 (4)
126.6
126.6
126.3
108.3 (8)
69.8 (5)
69.4 (5)
124.1
107.0 (10)
69.6 (5)
68.5 (5)
126.5
126.5
126.9
108.0 (9)
69.2 (5)
70.1 (5)
126.0
126.0
126.2
110.0 (9)
71.2 (6)
71.2 (5)
125.0
125.0
124.2
106.6 (9)
68.5 (6)
68.6 (5)
126.7
126.7
127.7
149.2 (3)
170.3 (3)
40.1 (3)
117.4 (3)
40.6 (4)
68.4 (4)
68.9 (3)
106.2 (4)
114.6 (3)
128.2 (4)
41.2 (3)
115.3 (4)
146.8 (3)
107.9 (4)
40.3 (3)
110.6 (3)
67.8 (4)
68.1 (4)
40.7 (4)
168.1 (3)
Acta Cryst. (2017). C73, 760-766
sup-13

supporting information
C39—Fe3—C35
C40—Fe3—C36
C33—Fe3—C36
C32—Fe3—C36
C34—Fe3—C36
C38—Fe3—C36
C39—Fe3—C36
C35—Fe3—C36
C40—Fe3—C31
C33—Fe3—C31
C32—Fe3—C31
C34—Fe3—C31
C38—Fe3—C31
C39—Fe3—C31
C35—Fe3—C31
C36—Fe3—C31
C40—Fe3—C37
C33—Fe3—C37
C32—Fe3—C37
C34—Fe3—C37
C38—Fe3—C37
C39—Fe3—C37
C35—Fe3—C37
C36—Fe3—C37
C31—Fe3—C37
C46—Fe4—C52
C46—Fe4—C55
C52—Fe4—C55
C46—Fe4—C50
C52—Fe4—C50
C55—Fe4—C50
C46—Fe4—C54
C52—Fe4—C54
C55—Fe4—C54
C50—Fe4—C54
C46—Fe4—C51
C52—Fe4—C51
C55—Fe4—C51
C50—Fe4—C51
C54—Fe4—C51
C46—Fe4—C53
C52—Fe4—C53
C55—Fe4—C53
C50—Fe4—C53
C54—Fe4—C53
C51—Fe4—C53
C46—Fe4—C47
C52—Fe4—C47
131.7 (3)
41.4 (3)
167.1 (4)
130.1 (3)
151.8 (4)
68.4 (3)
68.8 (3)
119.5 (4)
132.2 (4)
67.8 (4)
40.6 (4)
68.4 (3)
148.5 (3)
171.0 (3)
40.3 (3)
110.2 (3)
68.9 (3)
128.1 (4)
107.3 (3)
166.5 (4)
40.7 (3)
68.2 (3)
151.0 (4)
40.4 (3)
117.3 (3)
123.8 (4)
123.9 (4)
67.3 (4)
41.2 (3)
160.5 (4)
108.7 (4)
160.2 (4)
66.9 (4)
40.7 (4)
123.5 (4)
108.4 (4)
40.3 (5)
40.3 (5)
124.3 (4)
67.9 (4)
158.9 (4)
40.3 (4)
67.9 (4)
157.9 (4)
39.7 (4)
68.2 (4)
41.1 (3)
107.5 (4)
C68—C67—H67
C66—C67—H67
Fe5—C67—H67
C67—C68—C69
C67—C68—Fe5
C69—C68—Fe5
C67—C68—H68
C69—C68—H68
Fe5—C68—H68
C70—C69—C68
C70—C69—Fe5
C68—C69—Fe5
C70—C69—H69
C68—C69—H69
Fe5—C69—H69
C69—C70—C66
C69—C70—C71
C66—C70—C71
C69—C70—Fe5
C66—C70—Fe5
C71—C70—Fe5
O72—C71—O73
O72—C71—C70
O73—C71—C70
C74—O73—C71
O75—C74—O73
O75—C74—C76
O73—C74—C76
C80—C76—C77
C80—C76—C74
C77—C76—C74
C80—C76—Fe6
C77—C76—Fe6
C74—C76—Fe6
C78—C77—C76
C78—C77—Fe6
C76—C77—Fe6
C78—C77—H77
C76—C77—H77
Fe6—C77—H77
C77—C78—C79
C77—C78—Fe6
C79—C78—Fe6
C77—C78—H78
C79—C78—H78
Fe6—C78—H78
C80—C79—C78
C80—C79—Fe6
125.8
125.8
126.5
108.8 (8)
69.9 (5)
69.4 (5)
125.6
125.6
126.7
107.8 (7)
69.4 (5)
70.1 (5)
126.1
126.1
126.0
108.1 (7)
128.4 (7)
123.4 (8)
70.0 (5)
69.7 (4)
127.3 (6)
122.2 (7)
126.7 (8)
111.0 (7)
118.9 (6)
124.3 (8)
125.6 (8)
110.1 (7)
107.4 (8)
129.2 (8)
123.0 (8)
69.8 (5)
69.6 (5)
120.5 (6)
108.2 (8)
71.2 (5)
68.7 (4)
125.9
125.9
125.8
107.8 (8)
68.9 (5)
69.0 (5)
126.1
126.1
127.6
108.7 (8)
69.2 (5)
Acta Cryst. (2017). C73, 760-766
sup-14

supporting information
C55—Fe4—C47
C50—Fe4—C47
C54—Fe4—C47
C51—Fe4—C47
C53—Fe4—C47
C46—Fe4—C49
C52—Fe4—C49
C55—Fe4—C49
C50—Fe4—C49
C54—Fe4—C49
C51—Fe4—C49
C53—Fe4—C49
C47—Fe4—C49
C46—Fe4—C48
C52—Fe4—C48
C55—Fe4—C48
C50—Fe4—C48
C54—Fe4—C48
C51—Fe4—C48
C53—Fe4—C48
C47—Fe4—C48
C49—Fe4—C48
C35—C31—C32
C35—C31—Fe3
C32—C31—Fe3
C35—C31—H31
C32—C31—H31
Fe3—C31—H31
C33—C32—C31
C33—C32—Fe3
C31—C32—Fe3
C33—C32—H32
C31—C32—H32
Fe3—C32—H32
C32—C33—C34
C32—C33—Fe3
C34—C33—Fe3
C32—C33—H33
C34—C33—H33
Fe3—C33—H33
C33—C34—C35
159.6 (4)
69.2 (3)
157.5 (4)
123.0 (4)
121.9 (4)
68.6 (3)
157.8 (4)
123.9 (4)
40.5 (3)
107.9 (4)
160.1 (4)
121.8 (4)
68.5 (4)
68.9 (3)
121.6 (4)
159.3 (4)
69.2 (3)
122.1 (4)
157.8 (5)
105.9 (4)
40.6 (3)
41.1 (4)
107.6 (8)
69.7 (5)
69.2 (5)
126.2
126.2
126.5
107.9 (8)
69.8 (5)
70.2 (5)
126.1
126.1
125.6
109.3 (8)
70.1 (5)
69.9 (5)
125.4
C78—C79—Fe6
C80—C79—H79
C78—C79—H79
Fe6—C79—H79
C79—C80—C76
C79—C80—Fe6
C76—C80—Fe6
C79—C80—H80
C76—C80—H80
Fe6—C80—H80
C82—C81—C85
C82—C81—Fe6
C85—C81—Fe6
C82—C81—H81
C85—C81—H81
Fe6—C81—H81
C83—C82—C81
C83—C82—Fe6
C81—C82—Fe6
C83—C82—H82
C81—C82—H82
Fe6—C82—H82
C84—C83—C82
C84—C83—Fe6
C82—C83—Fe6
C84—C83—H83
C82—C83—H83
Fe6—C83—H83
C83—C84—C85
C83—C84—Fe6
C85—C84—Fe6
C83—C84—H84
C85—C84—H84
Fe6—C84—H84
C81—C85—C84
C81—C85—Fe6
C84—C85—Fe6
C81—C85—H85
C84—C85—H85
Fe6—C85—H85
70.1 (5)
125.6
125.6
126.6
107.9 (8)
70.4 (5)
69.0 (4)
126.1
126.1
126.1
108.5 (8)
69.5 (5)
70.1 (5)
125.8
125.8
126.3
107.5 (8)
69.2 (5)
69.7 (5)
126.3
126.3
126.4
109.4 (8)
70.6 (5)
70.0 (5)
125.3
125.3
125.7
107.8 (8)
69.1 (5)
69.7 (5)
126.1
126.1
126.6
106.8 (9)
68.9 (5)
69.1 (5)
126.6
126.6
127.0
125.4
126.2
106.9 (8)
C5—C1—C2—C3
Fe1—C1—C2—C3
C5—C1—C2—Fe1
C1—C2—C3—C4
Fe1—C2—C3—C4
C1—C2—C3—Fe1
−1.3 (10)
58.6 (6)
−60.0 (6)
1.0 (10)
59.4 (6)
−58.4 (6)
C41—O43—C44—O45
C41—O43—C44—C46
O45—C44—C46—C47
O43—C44—C46—C47
O45—C44—C46—C50
O43—C44—C46—C50
13.6 (12)
−169.4 (6)
−6.8 (13)
176.2 (7)
173.9 (9)
−3.1 (12)
Acta Cryst. (2017). C73, 760-766
sup-15

supporting information
C2—C3—C4—C5
−0.3 (10)
59.5 (6)
−59.8 (6)
1.1 (10)
−59.0 (6)
60.2 (6)
−0.5 (10)
59.0 (6)
−59.6 (6)
−0.3 (10)
−59.6 (6)
59.3 (6)
1.1 (10)
−58.2 (6)
59.3 (6)
O45—C44—C46—Fe4
−94.7 (10)
88.3 (8)
1.0 (9)
Fe1—C3—C4—C5
C2—C3—C4—Fe1
C2—C1—C5—C4
Fe1—C1—C5—C4
C2—C1—C5—Fe1
C3—C4—C5—C1
Fe1—C4—C5—C1
C3—C4—C5—Fe1
C10—C6—C7—C8
Fe1—C6—C7—C8
C10—C6—C7—Fe1
C6—C7—C8—C9
O43—C44—C46—Fe4
C50—C46—C47—C48
C44—C46—C47—C48
Fe4—C46—C47—C48
C50—C46—C47—Fe4
C44—C46—C47—Fe4
C46—C47—C48—C49
Fe4—C47—C48—C49
C46—C47—C48—Fe4
C47—C48—C49—C50
Fe4—C48—C49—C50
C47—C48—C49—Fe4
C48—C49—C50—C46
Fe4—C49—C50—C46
C48—C49—C50—Fe4
C47—C46—C50—C49
C44—C46—C50—C49
Fe4—C46—C50—C49
C47—C46—C50—Fe4
C44—C46—C50—Fe4
C55—C51—C52—C53
Fe4—C51—C52—C53
C55—C51—C52—Fe4
C51—C52—C53—C54
Fe4—C52—C53—C54
C51—C52—C53—Fe4
C52—C53—C54—C55
Fe4—C53—C54—C55
C52—C53—C54—Fe4
C52—C51—C55—C54
Fe4—C51—C55—C54
C52—C51—C55—Fe4
C53—C54—C55—C51
Fe4—C54—C55—C51
C53—C54—C55—Fe4
C65—C61—C62—C63
Fe5—C61—C62—C63
C65—C61—C62—Fe5
C61—C62—C63—C64
Fe5—C62—C63—C64
C61—C62—C63—Fe5
C62—C63—C64—C65
Fe5—C63—C64—C65
C62—C63—C64—Fe5
C62—C61—C65—C64
Fe5—C61—C65—C64
C62—C61—C65—Fe5
−178.4 (7)
−59.2 (6)
60.1 (5)
−119.3 (8)
−1.0 (9)
−58.9 (6)
57.9 (5)
0.7 (9)
−58.3 (6)
58.9 (6)
−0.1 (9)
−58.7 (5)
58.7 (6)
−0.6 (9)
178.8 (8)
59.9 (6)
−60.4 (5)
118.9 (8)
0.2 (11)
60.1 (7)
−59.9 (7)
−0.1 (11)
59.9 (6)
−60.0 (7)
−0.1 (10)
59.2 (6)
−59.2 (6)
−0.3 (11)
−59.8 (6)
59.5 (6)
0.2 (11)
59.9 (6)
−59.7 (7)
0.0 (10)
−59.4 (6)
59.3 (6)
0.4 (11)
Fe1—C7—C8—C9
C6—C7—C8—Fe1
C7—C8—C9—C10
Fe1—C8—C9—C10
C7—C8—C9—Fe1
C7—C6—C10—C9
Fe1—C6—C10—C9
C7—C6—C10—C11
Fe1—C6—C10—C11
C7—C6—C10—Fe1
C8—C9—C10—C6
Fe1—C9—C10—C6
C8—C9—C10—C11
Fe1—C9—C10—C11
C8—C9—C10—Fe1
C6—C10—C11—O12
C9—C10—C11—O12
Fe1—C10—C11—O12
C6—C10—C11—O13
C9—C10—C11—O13
Fe1—C10—C11—O13
O12—C11—O13—C14
C10—C11—O13—C14
C11—O13—C14—O15
C11—O13—C14—C16
O15—C14—C16—C20
O13—C14—C16—C20
O15—C14—C16—C17
O13—C14—C16—C17
O15—C14—C16—Fe2
O13—C14—C16—Fe2
C20—C16—C17—C18
C14—C16—C17—C18
Fe2—C16—C17—C18
C20—C16—C17—Fe2
−1.5 (9)
−59.1 (5)
57.7 (6)
−0.6 (9)
59.4 (5)
−179.4 (8)
−119.4 (8)
−60.0 (6)
1.3 (9)
−59.3 (6)
−179.8 (7)
119.6 (7)
60.6 (6)
−165.2 (8)
16.1 (13)
103.5 (9)
9.1 (12)
−169.5 (7)
−82.2 (8)
−31.4 (11)
154.0 (7)
−29.7 (12)
155.1 (7)
−172.2 (9)
2.8 (12)
−0.4 (13)
174.6 (7)
−84.9 (11)
90.1 (8)
−59.0 (6)
59.4 (6)
−0.5 (10)
−59.8 (6)
59.3 (6)
−0.3 (10)
59.2 (6)
−59.5 (6)
−0.1 (9)
−173.3 (7)
−60.1 (6)
60.0 (6)
Acta Cryst. (2017). C73, 760-766
sup-16

supporting information
C14—C16—C17—Fe2
C16—C17—C18—C19
Fe2—C17—C18—C19
C16—C17—C18—Fe2
C17—C18—C19—C20
Fe2—C18—C19—C20
C17—C18—C19—Fe2
C18—C19—C20—C16
Fe2—C19—C20—C16
C18—C19—C20—Fe2
C17—C16—C20—C19
C14—C16—C20—C19
Fe2—C16—C20—C19
C17—C16—C20—Fe2
C14—C16—C20—Fe2
C25—C21—C22—C23
Fe2—C21—C22—C23
C25—C21—C22—Fe2
C21—C22—C23—C24
Fe2—C22—C23—C24
C21—C22—C23—Fe2
C22—C23—C24—C25
Fe2—C23—C24—C25
C22—C23—C24—Fe2
C23—C24—C25—C21
Fe2—C24—C25—C21
C23—C24—C25—Fe2
C22—C21—C25—C24
Fe2—C21—C25—C24
C22—C21—C25—Fe2
C35—C31—C32—C33
Fe3—C31—C32—C33
C35—C31—C32—Fe3
C31—C32—C33—C34
Fe3—C32—C33—C34
C31—C32—C33—Fe3
C32—C33—C34—C35
Fe3—C33—C34—C35
C32—C33—C34—Fe3
C32—C31—C35—C34
Fe3—C31—C35—C34
C32—C31—C35—Fe3
C33—C34—C35—C31
Fe3—C34—C35—C31
C33—C34—C35—Fe3
C40—C36—C37—C38
Fe3—C36—C37—C38
C40—C36—C37—Fe3
−113.3 (8)
0.1 (10)
−58.3 (6)
58.4 (5)
0.0 (10)
−58.3 (6)
58.3 (6)
0.0 (10)
−59.2 (6)
59.2 (6)
0.1 (10)
172.7 (8)
60.4 (6)
−60.3 (6)
112.3 (9)
−2.2 (10)
59.2 (7)
−61.4 (6)
0.5 (11)
59.0 (7)
−58.5 (6)
1.3 (11)
60.9 (7)
−59.6 (7)
−2.6 (11)
58.3 (6)
−60.9 (7)
2.9 (10)
−58.2 (6)
61.1 (6)
0.5 (10)
59.9 (6)
−59.3 (6)
−1.0 (10)
59.1 (6)
−60.1 (6)
1.0 (10)
60.3 (6)
−59.2 (6)
0.1 (10)
−58.9 (6)
59.0 (6)
−0.7 (10)
59.3 (6)
−60.0 (6)
−0.4 (9)
−58.2 (6)
57.8 (5)
C63—C64—C65—C61
0.5 (10)
−59.4 (6)
60.0 (6)
0.1 (10)
59.2 (6)
−59.1 (6)
−0.4 (10)
58.6 (6)
−58.9 (6)
0.5 (10)
59.4 (6)
−58.9 (6)
−0.4 (9)
Fe5—C64—C65—C61
C63—C64—C65—Fe5
C70—C66—C67—C68
Fe5—C66—C67—C68
C70—C66—C67—Fe5
C66—C67—C68—C69
Fe5—C67—C68—C69
C66—C67—C68—Fe5
C67—C68—C69—C70
Fe5—C68—C69—C70
C67—C68—C69—Fe5
C68—C69—C70—C66
Fe5—C69—C70—C66
C68—C69—C70—C71
Fe5—C69—C70—C71
C68—C69—C70—Fe5
C67—C66—C70—C69
Fe5—C66—C70—C69
C67—C66—C70—C71
Fe5—C66—C70—C71
C67—C66—C70—Fe5
C69—C70—C71—O72
C66—C70—C71—O72
Fe5—C70—C71—O72
C69—C70—C71—O73
C66—C70—C71—O73
Fe5—C70—C71—O73
O72—C71—O73—C74
C70—C71—O73—C74
C71—O73—C74—O75
C71—O73—C74—C76
O75—C74—C76—C80
O73—C74—C76—C80
O75—C74—C76—C77
O73—C74—C76—C77
O75—C74—C76—Fe6
O73—C74—C76—Fe6
C80—C76—C77—C78
C74—C76—C77—C78
Fe6—C76—C77—C78
C80—C76—C77—Fe6
C74—C76—C77—Fe6
C76—C77—C78—C79
Fe6—C77—C78—C79
C76—C77—C78—Fe6
C77—C78—C79—C80
Fe6—C78—C79—C80
59.4 (6)
177.9 (8)
−122.3 (9)
−59.8 (6)
0.2 (9)
−59.6 (6)
−178.2 (7)
122.0 (8)
59.8 (6)
−162.6 (9)
15.4 (13)
104.2 (9)
13.3 (12)
−168.6 (7)
−79.8 (8)
−34.5 (11)
149.4 (7)
−21.9 (12)
160.0 (7)
−174.3 (9)
3.8 (12)
−2.1 (14)
176.0 (7)
−86.3 (11)
91.7 (8)
−0.6 (9)
−174.3 (8)
−60.5 (6)
59.8 (6)
−113.8 (7)
0.7 (10)
−58.2 (6)
58.9 (6)
−0.5 (10)
−58.7 (6)
Acta Cryst. (2017). C73, 760-766
sup-17

supporting information
C36—C37—C38—C39
Fe3—C37—C38—C39
C36—C37—C38—Fe3
C37—C38—C39—C40
Fe3—C38—C39—C40
C37—C38—C39—Fe3
C38—C39—C40—C36
Fe3—C39—C40—C36
C38—C39—C40—C41
Fe3—C39—C40—C41
C38—C39—C40—Fe3
C37—C36—C40—C39
Fe3—C36—C40—C39
C37—C36—C40—C41
Fe3—C36—C40—C41
C37—C36—C40—Fe3
C39—C40—C41—O42
C36—C40—C41—O42
Fe3—C40—C41—O42
C39—C40—C41—O43
C36—C40—C41—O43
Fe3—C40—C41—O43
O42—C41—O43—C44
C40—C41—O43—C44
−1.2 (9)
−59.8 (6)
58.5 (6)
2.4 (9)
−57.6 (6)
60.0 (6)
C77—C78—C79—Fe6
58.1 (6)
0.1 (10)
−59.1 (6)
59.2 (6)
0.3 (9)
C78—C79—C80—C76
Fe6—C79—C80—C76
C78—C79—C80—Fe6
C77—C76—C80—C79
C74—C76—C80—C79
Fe6—C76—C80—C79
C77—C76—C80—Fe6
C74—C76—C80—Fe6
C85—C81—C82—C83
Fe6—C81—C82—C83
C85—C81—C82—Fe6
C81—C82—C83—C84
Fe6—C82—C83—C84
C81—C82—C83—Fe6
C82—C83—C84—C85
Fe6—C83—C84—C85
C82—C83—C84—Fe6
C82—C81—C85—C84
Fe6—C81—C85—C84
C82—C81—C85—Fe6
C83—C84—C85—C81
Fe6—C84—C85—C81
C83—C84—C85—Fe6
173.4 (8)
60.0 (6)
−59.7 (6)
113.5 (9)
0.3 (11)
−59.2 (6)
59.4 (6)
−0.3 (11)
−59.8 (7)
59.4 (6)
0.2 (11)
−59.2 (6)
59.4 (7)
−0.2 (10)
58.9 (6)
−59.1 (6)
0.0 (10)
−58.8 (6)
58.8 (7)
−2.7 (9)
−61.2 (6)
177.4 (8)
118.9 (9)
58.5 (6)
1.9 (9)
61.2 (6)
−178.2 (7)
−118.9 (8)
−59.3 (6)
165.6 (9)
−14.3 (14)
−102.5 (9)
−12.0 (12)
168.1 (7)
80.0 (8)
42.5 (11)
−139.8 (7)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
C49—H49···O72
C31—H31···O12
C5—H5···O45i
0.95
0.95
0.95
0.95
0.95
0.95
0.95
0.95
0.95
0.95
2.64
2.49
2.56
2.57
2.73
2.33
2.65
2.66
2.79
2.35
3.516 (10)
3.387 (10)
3.367 (11)
3.438 (12)
3.017 (10)
3.255 (11)
3.127 (10)
3.595 (10)
3.084 (10)
3.273 (10)
153
158
142
152
98
164
112
170
99
C85—H85···O42ii
C6—H6···O12iii
C6—H6···O15iii
C39—H39···O42iii
C39—H39···O45iii
C69—H69···O72iv
C69—H69···O75iv
164
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x, −y+1, z−1/2; (iii) x−1, y, z; (iv) x+1, y, z.
Acta Cryst. (2017). C73, 760-766
sup-18