2,2′′,3,3′′,4,4′′,5, 5′′-Octa-phenyl-1,1′:4′,1′′-terphenyl and 2′,3′,5′,6′-tetra-fluoro-2,2′′,3, 3′′,4,4′′,5,5′′-octa-phenyl-1,1′: 4′,1′′-terphen-yl

Article abstract of DOI:10.1107/S0108270111051900

The title compounds, C66H46, (I), and C66H42F4, (II), are polyphenyl-ated aryl-enes synthesized by one-step Diels-Alder cyclo-addition reactions. In both structures, all mol-ecules lie on crystallographic inversion centers. In the case of (I), there are t

Full text of DOI:10.1107/S0108270111051900

organic compounds
˚
Acta Crystallographica Section C
Crystal Structure
Communications
and 2.642 (16) A, with approximate C—Hꢁ ꢁ ꢁF angles of 123
and 157ꢀ, respectively. These form a hydrogen-bonded ribbon
structure which propagates in the b-axis direction.
ISSN 0108-2701
Comment
2,200,3,300,4,400,5,500-Octaphenyl-
1,10:40,100-terphenyl and 20,30,50,60-
tetrafluoro-2,200,3,300,4,400,5,500-octa-
phenyl-1,10:40,100-terphenyl
Polyphenylated aromatic molecules are of interest as building
blocks in high-performance polymers, such as polyimides,
poly(aryl ether)s, poly(ether ketone)s and polysulfones, which
possess high glass transition (Tg) temperatures, high thermal
stability and good mechanical properties and, therefore, have
been identified for a variety of applications in government,
industry and academia (Yates & Hayes, 2004; Chae & Kumar,
2006). The steric bulk of the phenyl substituents forces the
polyphenylene backbone out of conjugation, making these
materials insulating and soluble in organic solvents (Berre-
sheim et al., 1999). The addition of fluorine onto the aromatic
molecules increases their oxidative stability (Drobny, 2001).
The Diels–Alder cycloaddition of biscyclopentadienones with
acetylenes has been widely used to produce polyphenylated
aromatics and polyarylenes (Stille et al., 1966; Rusanov et al.,
2006), including those used as polymer electrolytes for fuel
cells (Fujimoto et al., 2005). The former have often been used
as model compounds to help understand the regiochemistry in
the polymeric forms (Gagnon, Halperin et al., 2010; Gagnon,
Maris et al., 2010).
Stephen M. Budy,a Gary S. Nichola*‡ and Douglas A.
Loya,b
aDepartment of Chemistry and Biochemistry, The University of Arizona, Tucson,
AZ 85721, USA, and bDepartment of Materials Science and Engineering, The
University of Arizona, Tucson, AZ 85721, USA
Correspondence e-mail: g.s.nichol@ed.ac.uk
Received 21 October 2011
Accepted 1 December 2011
Online 9 December 2011
The title compounds, C66H46, (I), and C66H42F4, (II), are
polyphenylated arylenes synthesized by one-step Diels–Alder
cycloaddition reactions. In both structures, all molecules lie on
crystallographic inversion centers. In the case of (I), there are
two half-molecules present in the asymmetric unit, (IA) and
(IB); the geometry of each half-molecule differs principally in
the magnitudes of the dihedral angles between mean planes
fitted through the central aryl ring and the pendant phenyl
rings. The crystal used was a non-merohedral twin, with a
refined twin scale factor of 0.460 (8). The dihedral angle
between the plane of the central tetrafluorinated ring and the
adjacent tetraphenylated ring in (II) is 83.87 (4)ꢀ, significantly
greater than the dihedral angles of 49.89 (12) and 54.38 (10)ꢀ
found in the two half-molecules in (IA) and (IB), respectively,
and attributed to intermolecular C—Hꢁ ꢁ ꢁF hydrogen bonding
in (II). Intermolecular C—Hꢁ ꢁ ꢁꢀ bonding is found in (I). Two
interactions have the C—H bond oriented towards the
centroid (Cg) of a butadiene fragment of a phenyl ring; both
As part of our research we reinvestigated 2,200,3,300,-
4,400,5,500-octaphenyl-1,10:40100-terphenyl, (I), which was pre-
˚
Hꢁ ꢁ ꢁCg distances are approximately 2.68 A and the inter-
¨
viously reported (Ried & Bonnighausen, 1960) but without a
actions connect adjacent molecules into stacks in the c-axis
direction. The composition of the stacks alternates, i.e. (IA)–
(IB)–(IA)–(IB) etc. A third, weaker, C—Hꢁ ꢁ ꢁꢀ interaction
and a phenyl–phenyl close contact connect each end of the
long molecular axes of (IB) with an adjacent molecule of (IA)
into chains which run perpendicular to the (140) and (140)
planes. C—Hꢁ ꢁ ꢁF interactions in (II) have the most profound
influence on the molecular and crystal structure, the main
effect of which is the above-mentioned increase in the
dihedral angle between the plane of the central tetra-
fluorinated ring and the adjacent tetraphenylated ring. C—
Hꢁ ꢁ ꢁF interactions have refined Hꢁ ꢁ ꢁF distances of 2.572 (15)
crystal structure, while 20,30,50,60-tetrafluoro-2,200,3,300,4,400,-
5,500-octaphenyl-1,10:40,100-terphenyl, (II), has not been
previously reported. The molecular structures of the Diels–
Alder adducts (I) and (II) are presented here.
The asymmetric unit of (I) contains two half-molecules;
consequently, there are two crystallographically unique mol-
ecules, (IA) and (IB), that are generated from these half-
molecules by inversion symmetry. Both of these are shown in
Fig. 1. An overlay of (IA) with (IB), showing the relative
orientations of the various pendant and central phenyl rings, is
shown in Fig. 2. Selected dihedral angles for (IA) and (IB),
and for related compounds in the Cambridge Structural
Database (CSD; Version 5.21, plus four updates; Allen, 2002),
are provided in Table 1. Comparison of the dihedral angles for
‡ Present address: School of Chemistry, The University of Edinburgh, Joseph
Black Building, West Mains Road, Edinburgh EH9 3JJ, Scotland.
Acta Cryst. (2012). C68, o23–o27
doi:10.1107/S0108270111051900
# 2012 International Union of Crystallography o23

organic compounds
Figure 2
An overlay of molecule A (gray; orange in the electronic version of the
paper) with molecule B (black) in (I), formed by a least-squares fit of the
˚
six C atoms of ring 1, with an r.m.s. deviation of 0.0377 A. The ring-
numbering system is used to identify angles between least-squares planes.
Figure 1
The molecular structures of (IA) (top) and (IB) (bottom), with
displacement ellipsoids at the 50% probability level. Unlabeled atoms
are related to labeled atoms by crystallographic inversion symmetry.
(I) with PUNVOK in Table 1 reveals that those for (IA) and
(IB) are relatively typical except for the 1/4 and 1/5 dihedral
angles for (IA), both of which are noticeably elevated. The
large difference between 1 and 4 is likely the result of the role
of ring 4 in (IA) as an acceptor in a C—Hꢁ ꢁ ꢁꢀ interaction,
whereas ring 4 in (IB) is not involved in a similar interaction.
Similarly, in (IA), ring 5 is involved in C—Hꢁ ꢁ ꢁꢀ interactions
with (IB). In the case of ring 6 in (II), this is involved in
hydrogen bonding (discussed later). The values for PUNVEA
are included in Table 1 for the purpose of contrast, since in this
case C6 of the terphenyl core is substituted (i.e. C6-phenyl).
All of the dihedral angles in PUNVEA are elevated relative to
the rest of Table 1 owing to the presence of additional intra-
molecular steric crowding caused by the extra phenyl ring. It
should also be noted that several of the literature structures
are solvates, contain structural disorder, or are charged species
with bulky counter-ions; the presence of such additional
species in the asymmetric unit can make rationalization of
molecular conformation on the basis of intermolecular inter-
actions between chemically equivalent molecules rather diffi-
cult. However, in this case, the analysis in Table 1 shows a
reasonable degree of consistency between the dihedral angles.
Three unique intermolecular C—Hꢁ ꢁ ꢁꢀ interactions are
observed in (I) (Table 2). Two of these, C27—H27ꢁ ꢁ ꢁCgA and
C79—H79ꢁ ꢁ ꢁCgBii [symmetry code: (ii) x, y, z + 1], are best
described as having the C—H bond oriented towards the
Figure 3
C—Hꢁ ꢁ ꢁꢀ interactions, shown as dashed lines, in (I). The color scheme is
the same as used in Fig. 2. The long b axis has been truncated.
centroid of a butadiene fragment of an adjacent phenyl ring.
The H27ꢁ ꢁ ꢁCgA and H79ꢁ ꢁ ꢁCgBii distances are both
˚
approximately 2.68 A, where CgA and CgB are centroids
defined in Table 2. These interactions connect adjacent mol-
ecules into stacks in the c-axis direction; the composition of
the stacks alternates, i.e. (IA)–(IB)–(IA)–(IB) etc., and in
alternate layers the long molecular axis is rotated by
approximately 71ꢀ (Fig. 3).
The third interaction is between C66—H66 and the ꢀ-
electron density above C23i [symmetry code: (i) x þ 1, ꢂy + 12,
z + 12] and is much weaker than the previous two interactions,
i
˚
with an H66ꢁ ꢁ ꢁC23 distance of 2.85 A. In addition, there is an
intermolecular close contact between adjacent phenyl rings at
the ends of the molecules. The C66ꢁ ꢁ ꢁC16i distance is
˚
˚
3.255 (3) A, shorter than the van der Waals sum of 3.40 A for
two C atoms. The marked increase in the 1/4 dihedral angle in
(IA) is attributed to these two interactions. These two inter-
actions also connect each end of the long molecular axes of
(IB) with an adjacent molecule of (IA) into (IA)–(IB)–(IA)–
ꢃ
o24 Budy et al. C66H46 and C66H42F4
Acta Cryst. (2012). C68, o23–o27

organic compounds
Figure 4
The C—Hꢁ ꢁ ꢁꢀ-bonded chain in (I). C—Hꢁ ꢁ ꢁꢀ interactions are shown as dashed lines. The color scheme is the same as used in Fig. 2. The long b axis has
been truncated.
Figure 6
An overlay of (IB) and (II), fitted in the same way as for Fig. 2, with an
˚
r.m.s. deviation of 0.0278 A. (II) is shown in gray (green in the electronic
version of the paper).
Figure 5
Twice the asymmetric unit of (II), with displacement ellipsoids at the 70%
probability level. Unlabeled atoms are related to labeled atoms by
crystallographic inversion symmetry.
tetrafluorinated terphenyl model system, and the tetra-
fluorinated pentaphenylated version has not been synthesized
or reported in the literature.
(IB) etc. chains oriented perpendicular to the (140) and (140)
planes (an example of one such chain is given in Fig. 4). The
complete description of the crystal structure of (I) is a
combination of one-dimensional stacks and one-dimensional
chains, which combine to give two sets of interpenetrated
three-dimensional networks of intermolecularly associated
molecules.
The presence of C—Hꢁ ꢁ ꢁF interactions in (II) is a notable
feature (Fig. 7 and Table 3). All F atoms are involved in these
interactions, which form a hydrogen-bonded ribbon structure
which propagates in the b-axis direction. The shortest Fꢁ ꢁ ꢁF
˚
distance (3.19 A) is longer than the van der Waals sum for two
˚
F atoms (2.91 A) and so Fꢁ ꢁ ꢁF close contacts are unlikely in
The asymmetric unit of (II) contains just one half-molecule
of the tetrafluorinated adduct. A whole molecule of (II),
consisting of two asymmetric units related by crystallographic
inversion symmetry, is shown in Fig. 5 and selected dihedral
angles are given in Table 1. The 1/6 dihedral angle in (II) is
83.87 (4)ꢀ, while the corresponding angles in (IA), (IB) and
perfluorobiphenyl (Naae, 1979) are 49.89 (12), 54.38 (3) and
59.6ꢀ, respectively. As shown in Fig. 6, larger 1/6 values
correspond to a more twisted and less planar terphenyl core. A
broader survey of related compounds (Table 1) shows that the
1/6 angle for (II) is unusual, over 20ꢀ greater than all others.
This can be attributed to the participation of the F atoms in
C—Hꢁ ꢁ ꢁF hydrogen bonding, as discussed below. The
aromatic C—F bond distances are consistent with typical
this structure. Therefore, the formation of C—Hꢁ ꢁ ꢁF inter-
actions in (II) is the main driving force behind the significant
nonplanar topology of the terphenyl core, as evidenced by the
magnitude of the 1/6 angle in (II). By contrast, C—Hꢁ ꢁ ꢁꢀ
interactions are hindered. The only exception to this is a long
H27ꢁ ꢁ ꢁC16iii interaction (details and symmetry code are in
Table 3) which is between adjacent ribbons in the crystal
packing and has no role in the topology of the terphenyl core.
It is well known that meta- and para-substituted biphenyls
and biphenyl itself have a planar configuration (Bastiansen,
1949), whereas extensive studies on terphenyl show it to be
nonplanar at low temperature (Baudour et al., 1977, 1986). For
polyphenylated terphenyl and similar compounds, Gagnon,
Maris et al. (2010) noted that such compounds generally lack
aromatic interactions, attributed to the nonplanar topology of
the molecules, which hinders close packing. Here we show that
˚
values for ortho-F atoms, approximately 0.02 A shorter than
other types of Ar—F bond (Ar is aryl; Allen et al., 1987).
There is no crystal structure with which to compare the
ꢃ
Acta Cryst. (2012). C68, o23–o27
Budy et al. C66H46 and C66H42F4 o25

organic compounds
Table 1
Selected dihedral angles (ꢀ) in (I), (II) and related compounds.
Dihedral angles are between least-squares planes fitted through all non-H
atoms of the pendant phenyl rings and the central aryl ring; rings are
numbered according to the system described in Fig. 2. Compounds with
multiple entries contain more than one pentaphenylated component. Dihedral
angles for (IA), (IB) and (II) were calculated using SHELXTL (Sheldrick,
2008b); all other dihedral angles were determined using PLATON (Spek,
2009). Ring 6 of PUNVEA contains an extra phenyl ring, 7; the dihedral angle
6/7 in PUNVEA is 85.59 (6)ꢀ.
Compound
1/2
1/3
1/4
1/5
1/6
(IA)
(IB)
(II)
BIJBECa
58.66 (8)
49.24 (8)
64.10 (3)
61.53 (17)
45.63 (17)
55.0 (3)
67.55 (7)
65.82 (7)
60.42 (4)
56.17 (15)
62.99 (15)
55.9 (3)
86.08 (6)
64.44 (6)
55.83 (4)
67.30 (16)
65.35 (16)
64.3 (3)
73.56 (7)
67.21 (6)
66.17 (3)
67.56 (16)
64.22 (17)
54.4 (3)
49.89 (12)
54.38 (10)
83.87 (4)
51.33 (15)
53.07 (15)
46.7 (3)
EGIKUA†b
55.6 (3)
56.5 (4)
66.6 (3)
61.1 (3)
63.3 (3)
66.4 (3)
60.1 (3)
61.1 (3)
48.3 (3)
44.9 (3)
60.7 (4)
62.2 (3)
55.0 (3)
50.76 (4)
49.17 (3)
48.63 (17)
56.09 (7)
49.83 (8)
69.19 (6)
61.4 (3)
60.2 (4)
55.9 (3)
54.20 (4)
58.47 (3)
64.88 (15)
58.12 (7)
63.93 (8)
77.36 (6)
64.1 (4)
68.0 (4)
64.3 (3)
71.12 (4)
63.13 (3)
66.37 (15)
72.92 (7)
62.78 (9)
80.79 (8)
57.2 (4)
54.2 (4)
54.4 (3)
63.68 (3)
57.10 (4)
67.75 (15)
58.13 (7)
61.33 (9)
85.67 (6)
38.7 (3)
42.3 (3)
46.7 (3)
47.59 (3)
50.46 (3)
50.16 (14)
57.18 (7)
60.35 (8)
61.26 (5)
IQESIH†c
NILQABd
PUNVIEe
PUNVOKe
PUNVEAe
Figure 7
† Structure contains solvent or counter-ion. References for CSD refcodes: (a) Grebel-
¨
Koehler et al. (2003); (b) Bauer et al. (2002); (c) Turp et al. (2011); (d) Chen et al. (2007);
Gagnon, Maris et al. (2010).
C—Hꢁ ꢁ ꢁF and ꢀ–ꢀ interactions (dotted lines) in (II). The a axis has been
truncated.
close packing interactions do indeed exist between aromatic
rings in this type of compound, although they are few in
number when compared with the number of aromatic rings
present. Indeed, quite dramatic changes in both molecular
conformation and three-dimensional structure can be effected
by fluorine substitution at the central aryl ring, which result in
newly formed C—Hꢁ ꢁ ꢁF intermolecular interactions, an
entirely different molecular conformation and hence a quite
different crystal structure.
Table 2
ꢀ
˚
Intermolecular ꢀ-interactions (A, ) in (I).
CgA is the centroid of atoms C52/C53/C54/C55 and CgB is the centroid of
atoms C1/C4/C5/C6.
D—Hꢁ ꢁ ꢁA
D—H
Hꢁ ꢁ ꢁA
Dꢁ ꢁ ꢁA
D—Hꢁ ꢁ ꢁA
C27—H27ꢁ ꢁ ꢁCgA
C66—H66ꢁ ꢁ ꢁC23i
C79—H79ꢁ ꢁ ꢁCgBii
Symmetry codes: (i) x þ 1; ꢂy þ ; z þ ; (ii) x; y; z þ 1.
0.95
0.95
0.95
2.68
2.85
2.68
3.58
3.701 (3)
3.61
157
150
165
1
2
1
2
Experimental
Compound (I)
1,4-Diethynylbenzene was obtained from Aldrich and purified by
sublimation before use. 2,3,4,5-Tetraphenylcyclopentadienone (tetra-
cyclone) was synthesized according to published methods (Johnson &
Grummitt, 1943) and crystallized from a mixture of ethanol and
benzene. 1,4-Diethynyl-2,3,5,6-tetrafluorobenzene was synthesized
according to previous methods and sublimed before use (Neenan &
Whitesides, 1988). Diels–Alder adducts (I) and (II) were obtained by
the reaction between 1,4-diethynylbenzene (57 mg, 0.455 mmol) or
1,4-diethynyl-2,3,5,6-tetrafluorobenzene (90 mg, 0.455 mmol), res-
pectively, with tetracyclone (350 mg, 0.910 mmol) under argon in
diphenyl ether (5 ml) in a round-bottomed flask at 423 K for 24 h or
until the color changed from dark purple to yellow or pink, respec-
tively. The products were cooled to room temperature, precipitated
with acetone (100 ml) and vacuum filtered; the solid was washed with
acetone (10 ml) and dried in a vacuum oven at 333 K for 24 h,
affording white solids in yields of 78 and 84%, respectively. In both
cases, crystals suitable for X-ray analysis were grown from solutions
(10–20 mg) in deuterated dimethyl sulfoxide (DMSO-d6, 5–10 ml).
Details of nuclear magnetic resonance assignments and high-resolu-
tion mass spectrometry are given in the archived CIF.
Crystal data
3
˚
V = 4597.1 (14) A
Z = 4
Mo Kꢂ radiation
ꢃ = 0.07 mmꢂ1
T = 100 K
C66H46
Mr = 839.03
Monoclinic, P21=c
˚
˚
a = 11.674 (2) A
b = 33.336 (6) A
˚
c = 11.816 (2) A
0.35 ꢄ 0.09 ꢄ 0.08 mm
ꢁ = 91.479 (3)ꢀ
Data collection
Bruker Kappa APEXII DUO CCD
diffractometer
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2008a)
Tmin = 0.977, Tmax = 0.995
40040 measured reflections
11292 independent reflections
8284 reflections with I > 2ꢄ(I)
Rint = 0.068
ꢅmax = 23.6ꢀ
Refinement
R[F2 > 2ꢄ(F2)] = 0.043
wR(F2) = 0.107
S = 1.04
596 parameters
H-atom parameteꢂrs3 constrained
˚
Áꢆmax = 0.16 e A
ꢂ3
˚
11292 reflections
Áꢆmin = ꢂ0.22 e A
ꢃ
o26 Budy et al. C66H46 and C66H42F4
Acta Cryst. (2012). C68, o23–o27

organic compounds
Table 3
Intermolecular hydrogen bonding and ꢀ-interactions (A, ) in (II).
(Macrae et al., 2008); software used to prepare material for publica-
tion: SHELXTL, publCIF (Westrip, 2010) and local programs.
ꢀ
˚
D—Hꢁ ꢁ ꢁA
D—H
Hꢁ ꢁ ꢁA
Dꢁ ꢁ ꢁA
D—Hꢁ ꢁ ꢁA
SMB specifically recognizes the Diversity Fellowship for
Underrepresented Students. The authors thank the Nuclear
Magnetic Resonance and Mass Spectrometry facilities of the
University of Arizona. The diffractometer was purchased with
funding from NSF grant No. CHE-0741837. This research was
funded by Energy Materials Corporation (EMC) and the
University of Arizona.
C30—H30ꢁ ꢁ ꢁF1i
0.981 (16)
0.967 (16)
1.000 (16)
2.572 (15)
2.642 (16)
2.825 (16)
3.2084 (11)
3.5517 (12)
3.6927 (14)
122.6 (11)
157.0 (12)
145.5 (12)
C8—H8ꢁ ꢁ ꢁF2ii
C27—H27ꢁ ꢁ ꢁC16iii
1
2
1
2
1
2
Symmetry codes: (i) x; y þ 1; z; (ii) x; y ꢂ 1; z; (iii) x ꢂ ; ꢂy þ ; z ꢂ .
Compound (II)
Crystal data
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: EG3079). Services for accessing these data are
described at the back of the journal.
3
˚
C66H42F4
Mr = 911.00
V = 2329.89 (19) A
Z = 2
Monoclinic, P21=n
Mo Kꢂ radiation
ꢃ = 0.09 mmꢂ1
T = 100 K
0.31 ꢄ 0.19 ꢄ 0.16 mm
˚
a = 19.7494 (9) A
˚
b = 6.1217 (3) A
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c = 20.4762 (10) A
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400 parameters
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ꢂ3
˚
Áꢆmax = 0.44 e A
ꢂ3
˚
6808 reflections
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For (I), the crystal used was found to exhibit non-merohedral
twinning, which was handled by a combination of CELL_NOW
(Sheldrick, 2004) and TWINABS (Sheldrick, 2008a), with successive
refinement of the unit-cell parameters by SAINT (Bruker, 2007). The
twin law is 100/010/001 and the refined twin scale factor is 0.460 (8)
(3782 unique reflections involve domain 1, 3715 unique reflections
involve domain 2 and 4039 overlapped reflections involve both
˚
domains). Diffraction was only observed to a resolution of 0.89 A and
so the data set was truncated at this limit. H atoms were initially
located from a difference Fourier map, but were then constrained to
˚
ride on their parent atoms, with a C—H distance of 0.95 A and with
Naae, D. G. (1979). Acta Cryst. B35, 2765–2768.
Neenan, T. X. & Whitesides, G. M. (1988). J. Org. Chem. 53, 2489–2496.
¨
Ried, W. & Bonnighausen, K. H. (1960). Chem. Ber. 93, 1769–1773.
Uiso(H) = 1.2Ueq(C). For (II), all H atoms were located in a difference
map and were freely refined. C—H distances lie in the range
Rusanov, A. L., Likhachev, D. Y., Kozlova, O. V. & Harris, F. W. (2006). Prog.
Polym. Sci. 31, 749–810.
Sheldrick, G. M. (2004). CELL_NOW. University of Go¨ttingen, Germany.
˚
˚
0.962 (16)–1.015 (14) A. The largest residual peak is 0.69 A from
atom C33.
¨
Sheldrick, G. M. (2008a). TWINABS. University of Gottingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Stille, J. K., Harris, F. W., Rakutis, R. O. & Mukamal, H. (1966). J. Polym. Sci.
B, 4, 791–793.
For both compounds, data collection: APEX2 (Bruker, 2007). Cell
refinement: CELL_NOW (Sheldrick, 2004) and SAINT (Bruker,
2007) for (I); SAINT for (II). For both compounds, data reduction:
SAINT; program(s) used to solve structure: SHELXTL (Sheldrick,
2008b); program(s) used to refine structure: SHELXTL; molecular
graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury
¨ ¨
Turp, D., Wagner, M., Enkelmann, V. & Mullen, K. (2011). Angew. Chem. Int.
Ed. 50, 4962–4965.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
Yates, C. R. & Hayes, W. (2004). Eur. Polym. J. 40, 1257–1281.
ꢃ
Acta Cryst. (2012). C68, o23–o27
Budy et al. C66H46 and C66H42F4 o27