Head-to-tail square-shaped cyclic hydrogen bonds leading to dimeric aggregates: 1,8-dibenzoyl-2,7-dihydroxynaphthalene and a comparison with its analogous benzoylnaphthalene

Article abstract of DOI:10.1107/S0108270113030771

The title compound, C₂₄H₁₆O₄, crystallized with two independent molecules in the asymmetric unit. Both carbonyl groups in these molecules form intramolecular O - H...O=C hydrogen bonds with neighbouring hydroxy groups, affording six-membered cyclic structures. In the crystal, dimeric aggregates arise from two intermolecular O - H...O=C hydrogen bonds between both independent molecules, forming head-to-tail square-shaped cyclic ...O...H...O...H... hydrogen bonds. These dimeric aggregates are connected into layers in the bc plane by intermolecular (naphthalene)C - H...O=C interactions. On the other hand, the analogous compound bearing methoxy groups at the 2- and 7-positions of the naphthalene ring, namely 1,8-dibenzoyl-2,7- dimethoxynaphthalene [Nakaema et al. (2008). Acta Cryst. E64, o807], forms a three-dimensional molecular network via C - H...O=C and π-π interactions between the benzoyl groups. These results show that the intramolecular O - H...O=C hydrogen bonds in the title compound control the orientations of the benzoyl groups and thus promote the formation of the cyclic intermolecular O - H...O=C interactions involving the same donor and acceptor groups in pairs of molecules.

Full text of DOI:10.1107/S0108270113030771

organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
properties and various applications, e.g. optical and electronic
properties, and the applications based on the properties for
optically active polymers and catalysts, organic fluorescent
dyes and light-emitting diodes (Alfonso et al., 2007; Gasparrini
et al., 2008; Zhang et al., 2011). Peri-substituted naphthalenes
have also received much attention as characteristic structured
aromatic core compounds for a variety of functional materials
(Mei et al., 2006; Shinamura et al., 2010; Jiang et al., 2010).
Therefore, structural analyses have been actively performed
(Gore et al., 1980; Cohen et al., 2004; Jing et al., 2005).
Recently, we have revealed that diaroylation at the 1- and 8-
positions of naphthalene proceeds smoothly (Okamoto &
Yonezawa, 2009; Okamoto et al., 2011).
ISSN 0108-2701
Head-to-tail square-shaped cyclic
hydrogen bonds leading to dimeric
aggregates: 1,8-dibenzoyl-2,7-di-
hydroxynaphthalene and a
comparison with its analogous
benzoylnaphthalene
Saki Mohri,a Sayaka Yoshiwaka,a Katsuhiro Isozaki,b
Noriyuki Yonezawaa and Akiko Okamotoa*
aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of
Agriculture & Technology (TUAT), Koganei, Tokyo 184-8588, Japan, and bInter-
national Research Center for Elements Science, Institute for Chemical Research,
Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan
Correspondence e-mail: aokamoto@cc.tuat.ac.jp
According to X-ray crystal structure studies, the resulting
1,8-diaroylated naphthalene derivatives, such as 1,8-diben-
zoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008), have a
noncoplanar organization of the aromatic rings. Herein, the
X-ray crystal structure of the title compound, 1,8-dibenzoyl-
2,7-dihydroxynaphthalene, (I), is reported. The compound has
hydroxy groups at the 2- and 7-positions of the naphthalene
ring in place of the alkoxy groups of the above-mentioned
compound. We report the single-crystal structure and the
molecular packing of (I), and discuss the structure-deter-
mining factors through comparison with the analogous dime-
thoxy molecule.
Received 3 October 2013
Accepted 8 November 2013
The title compound, C24H16O4, crystallized with two indepen-
dent molecules in the asymmetric unit. Both carbonyl groups
in these molecules form intramolecular O—Hꢀ ꢀ ꢀO
C
hydrogen bonds with neighbouring hydroxy groups, affording
six-membered cyclic structures. In the crystal, dimeric aggre-
gates arise from two intermolecular O—Hꢀ ꢀ ꢀO C hydrogen
bonds between both independent molecules, forming head-to-
tail square-shaped cyclic ꢀ ꢀ ꢀOꢀ ꢀ ꢀHꢀ ꢀ ꢀOꢀ ꢀ ꢀHꢀ ꢀ ꢀ hydrogen
bonds. These dimeric aggregates are connected into layers in
the bc plane by intermolecular (naphthalene)C—Hꢀ ꢀ ꢀO
C
interactions. On the other hand, the analogous compound
bearing methoxy groups at the 2- and 7-positions of the
naphthalene ring, namely 1,8-dibenzoyl-2,7-dimethoxynaph-
thalene [Nakaema et al. (2008). Acta Cryst. E64, o807], forms a
three-dimensional molecular network via C—Hꢀ ꢀ ꢀO C and
ꢀ–ꢀ interactions between the benzoyl groups. These results
show that the intramolecular O—Hꢀ ꢀ ꢀO C hydrogen bonds
in the title compound control the orientations of the benzoyl
groups and thus promote the formation of the cyclic
intermolecular O—Hꢀ ꢀ ꢀO C interactions involving the same
donor and acceptor groups in pairs of molecules.
2. Experimental
2.1. Synthesis and crystallization
To the solution of 1,8-dibenzoyl-2,7-diethoxynaphthalene
(5.0 mmol, 2.1 g) and toluene (25 ml), AlCl3 (25.0 mmol, 3.3 g)
was added and the resulting solution stirred at 363 K for 1 h.
The reaction mixture was poured into 2 M aqueous HCl and
the mixture was extracted with CHCl3. The combined extracts
were washed with brine and dried over anhydrous MgSO4.
The solvent was removed under reduced pressure to give a
cake of the crude material. The crude product was purified by
recrystallization from chloroform and methanol (4:1 v/v).
Single crystals suitable for X-ray diffraction were obtained by
crystallization from toluene (48% isolated yield; m.p. 501.4–
Keywords: crystal structure; cyclic hydrogen bonds; 1,8-
dibenzoyl-2,7-dihydroxynaphthalene; O—Hꢀ ꢀ ꢀO C hydrogen
bonds.
1
502.1 K). H NMR (300 MHz, CDCl3): ꢁ 7.13 (2H, d, J =
8.9 Hz), 7.19 [4H, d (broad), J = 7.6 Hz], 7.30 (4H t, J = 7.6 Hz),
7.50 (2H, t, J = 7.6 Hz), 7.92 (2H, d, J = 8.9 Hz), 11.24 (2H, s).
13C NMR (75 MHz, CDCl3): ꢁ 115.39, 117.13, 122.16, 128.17,
131.61, 132.82, 133.00, 136.38, 136.49, 161.99, 197.26. IR (KBr,
cmꢁ1): 3441 (O—H), 1661 (C O), 1595, 1513, 1451 (Ar,
1. Introduction
Molecules with noncoplanar aromatic rings, such as binaph-
thyl and biphenyl compounds, have been in the limelight
because of their unique spatial shapes affording characteristic
Acta Cryst. (2013). C69, 1541–1544
doi:10.1107/S0108270113030771
# 2013 International Union of Crystallography 1541

organic compounds
Table 1
Experimental details.
Crystal data
Chemical formula
Mr
C24H16O4
368.37
Crystal system, space group
Temperature (K)
Monoclinic, P21/c
173
8.502 (3), 15.446 (5), 27.071 (10)
96.226 (4)
3534 (2)
8
Mo Kꢃ
0.09
˚
a, b, c (A)
ꢂ (ꢂ)
3
˚
V (A )
Z
Radiation type
ꢄ (mmꢁ1
Crystal size (mm)
)
0.40 ꢄ 0.15 ꢄ 0.15
Data collection
Diffractometer
Absorption correction
Rigaku Saturn70 diffractometer
Numerical (NUMABS; Higashi,
1999)
Tmin, Tmax
0.963, 0.986
23077, 6159, 4828
No. of measured, independent and
observed [I > 2ꢅ(I)] reflections
Rint
0.053
0.595
ꢁ1
˚
(sin ꢆ/ꢇ)max (A
)
Refinement
R[F2 > 2ꢅ(F2)], wR(F2), S
No. of reflections
No. of parameters
0.050, 0.118, 1.09
6159
509
H-atom parameters constrained
H-atom treatment
˚
ꢁ3
Áꢈmax, Áꢈmin (e A
)
0.16, ꢁ0.18
Computer programs: CrystalClear (Rigaku/MSC, 2006), Il Milione (Burla et al., 2007),
SHELXL97 (Sheldrick, 2008) and ORTEPIII (Burnett & Johnson, 1996).
naphthalene). Elemental analysis calculated for C24H16O4: C
78.25, H 4.38%; found: C 78.10, H 4.41%.
2.2. Refinement
Crystal data, data collection and structure refinement
details are summarized in Table 1. All H atoms could be
located in difference Fourier maps, but were subsequently
refined in optimized positions as riding atoms, with O—H =
˚
0.84 A and Uiso(H) = 1.5Ueq(O) for hydroxy H atoms, and
˚
C—H = 0.95 A and Uiso(H) = 1.2Ueq(C) for aromatic H atoms.
3. Results and discussion
Figure 1
There are two independent molecules (A and B) in the
asymmetric unit of (I) which display intramolecular O—
Hꢀ ꢀ ꢀO C hydrogen bonds between the hydroxy and
carbonyl groups (Fig. 1). Each independent molecule has
essentially the same noncoplanar organization of aromatic
The molecular structure of the title compound, showing (a) molecule A
and (b) molecule B, together with the atom-numbering schemes.
Displacement ellipsoids are drawn at the 50% probability level.
rings, as indicated by a least-squares fit of the two molecules
˚
(r.m.s. deviation = 0.003 A). The dihedral angles between the
Table 2
Hydrogen-bond geometry (A, ).
planes of the benzene rings are 9.10 (11) (for molecule A) and
2.37 (10)ꢂ (for molecule B), and those between the planes of
the benzene rings and the naphthalene system are 62.77 (10)
and 56.43 (8)ꢂ (for molecule A), and 54.68 (8) and 54.74 (9)ꢂ
(for molecule B).
In the crystal packing, the molecules are related only by
noncrystallographic centres of inversion. Independent mole-
cules A and B are connected into a supramolecular dimer via
head-to-tail square-shaped cyclic hydrogen bonds involving
two intermolecular C Oꢀ ꢀ ꢀH hydrogen bonds between the
hydroxy H atoms and the carbonyl O atoms (Table 2 and
ꢂ
˚
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
O3—H3Aꢀ ꢀ ꢀO1
O4—H4Aꢀ ꢀ ꢀO2
O4—H4Aꢀ ꢀ ꢀO5i
O7—H7Aꢀ ꢀ ꢀO2ii
O7—H7Aꢀ ꢀ ꢀO5
O8—H8Aꢀ ꢀ ꢀO6
C3—H3ꢀ ꢀ ꢀO6
0.84
0.84
0.84
0.84
0.84
0.84
0.95
0.95
1.91
1.90
2.39
2.26
1.92
1.83
2.59
2.57
2.631 (2)
2.616 (2)
2.989 (2)
2.843 (2)
2.635 (2)
2.557 (2)
3.542 (3)
3.401 (3)
143
142
129
126
143
144
178
146
C21—H21ꢀ ꢀ ꢀO4iii
1
1
2
1
2
1
2
Symmetry codes: (i) x ꢁ 1; ꢁy þ ; z þ ; (ii) x þ 1; ꢁy þ ; z ꢁ ; (iii) ꢁx þ 1,
2
1
2
3
2
y ꢁ ; ꢁz þ .
ꢃ
1542 Mohri et al. C24H16O4
Acta Cryst. (2013). C69, 1541–1544

organic compounds
Figure 4
A partial packing diagram of compound (II), viewed down the b axis. The
dashed lines indicate hydrogen bonds.
Figure 2
A partial view of the crystal packing of the title compound, showing the
Several years ago, we published the crystal structure of a
1,8-dibenzoylnaphthalene analogue bearing methoxy groups
at the 2- and 7-positions, namely 1,8-dibenzoyl-2,7-dimeth-
oxynaphthalene, (II) (Nakaema et al., 2008; Fig. 3). The mol-
ecules are located on twofold rotation axes. The molecular
packing differs strikingly from that of (I). In the crystal of (II),
a three-dimensional molecular network is formed by benzene
and methyl C—Hꢀ ꢀ ꢀO C interactions and benzene–benzene
ꢀ–ꢀ stacking interactions (Fig. 4). The dihedral angle between
the planes of the benzene ring and the naphthalene system in
(II) is larger than the corresponding values for (I) mentioned
earlier.
intermolecular O—Hꢀ ꢀ ꢀO and C—Hꢀ ꢀ ꢀO hydrogen bonds (see Table 1
1
for details). [Symmetry codes: (i) x ꢁ 1, ꢁy + 12, z + 21; (ii) x + 1, ꢁy + 21, z ꢁ ;
2
1
2
3
2
(iii) ꢁx + 1, y ꢁ , ꢁz + .]
Fig. 2). The dimeric aggregates are arranged in layers in the bc
plane by C—Hꢀ ꢀ ꢀO C hydrogen bonds between the naph-
thalene rings and the carbonyl groups not involved in the
formation of the square-shaped cyclic hydrogen bonds (C3—
H3ꢀ ꢀ ꢀO6; Table 2 and Fig. 2). Intermolecular C—Hꢀ ꢀ ꢀO
interactions between the benzene rings of the benzoyl groups
and the hydroxy groups (C21—H21ꢀ ꢀ ꢀO4iii; Table 2 and Fig. 2)
contribute to the stability of the molecular alignments along
the b axis.
The data indicate that intramolecular O—Hꢀ ꢀ ꢀO
C
hydrogen bonds constrain the orientations of the benzoyl
groups in (I). The constrained benzoyl groups might be
retarded the formation of three-dimensional molecular
network through C—Hꢀ ꢀ ꢀO and ꢀ–ꢀ interactions as the
methoxy analogue (II). Consequently, the cyclic inter-
molecular O—Hꢀ ꢀ ꢀO C interactions involving the same
donor and acceptor groups in pairs of molecules contribute to
the stabilization of the molecular packing of (I).
The authors express their gratitude to Associate Professor
Hikaru Takaya and Professor Masaharu Nakamura, Institute
for Chemical Research, Kyoto University, for their kind
advice. This work was partially supported by the Collaborative
Research Program of the Institute for Chemical Research,
Kyoto University (grant No. 2012–72).
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: FG3312). Services for accessing these data are
described at the back of the journal.
Figure 3
The molecular structure of 1,8-dibenzoyl-2,7-dimethoxynaphthalene
(Nakaema et al., 2008), showing the atom-labelling scheme and with
displacement ellipsoids drawn at the 50% probability level [symmetry
References
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2
ꢃ
Acta Cryst. (2013). C69, 1541–1544
Mohri et al. C24H16O4 1543

organic compounds
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1544 Mohri et al. C24H16O4
Acta Cryst. (2013). C69, 1541–1544

supplementary materials
supplementary materials
Acta Cryst. (2013). C69, 1541-1544 [doi:10.1107/S0108270113030771]
Head-to-tail square-shaped cyclic hydrogen bonds leading to dimeric
aggregates: 1,8-dibenzoyl-2,7-dihydroxynaphthalene and a comparison with its
analogous benzoylnaphthalene
Saki Mohri, Sayaka Yoshiwaka, Katsuhiro Isozaki, Noriyuki Yonezawa and Akiko Okamoto
Computing details
Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction:
CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: Il Milione (Burla et al., 2007); program(s) used to
refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used
to prepare material for publication: SHELXL97 (Sheldrick, 2008).
1,8-Dibenzoyl-2,7-dihydroxynaphthalene
Crystal data
C24H16O4
Mr = 368.37
F(000) = 1536
Dx = 1.385 Mg m−3
Mo Kα radiation, λ = 0.71070 Å
Cell parameters from 9173 reflections
θ = 2.0–31.2°
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 8.502 (3) Å
b = 15.446 (5) Å
c = 27.071 (10) Å
β = 96.226 (4)°
V = 3534 (2) Å3
Z = 8
µ = 0.09 mm−1
T = 173 K
Block, colourless
0.40 × 0.15 × 0.15 mm
Data collection
Rigaku Saturn70
diffractometer
23077 measured reflections
6159 independent reflections
4828 reflections with I > 2σ(I)
Rint = 0.053
Radiation source: rotating anode
Graphite monochromator
Detector resolution: 7.314 pixels mm-1
ω scans
Absorption correction: numerical
(NUMABS; Higashi, 1999)
θ
max = 25.0°, θmin = 3.0°
h = −7→10
k = −18→18
l = −32→32
T
min = 0.963, Tmax = 0.986
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.050
wR(F2) = 0.118
0 restraints
Primary atom site location: structure-invariant
direct methods
Secondary atom site location: difference Fourier
map
S = 1.09
6159 reflections
509 parameters
Hydrogen site location: inferred from
neighbouring sites
Acta Cryst. (2013). C69, 1541-1544
sup-1

supplementary materials
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0481P)2 + 0.7407P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.16 e Å−3
Δρmin = −0.17 e Å−3
Special details
Experimental. Spectroscopic data for the title compound: 1H NMR δ (300 MHz, CDCl3): 7.13 (2H, d, J = 8.9 Hz), 7.19
(4H, d, J=7.6 Hz), 7.30 (4H, t, J = 7.6 Hz), 7.50 (2H, tt, J = 7.6 Hz), 7.92 (2H, d, J = 8.9 Hz), 11.24(2H, s) p.p.m. 13 C
NMR δ (75 MHz, CDCl3): 115.39, 117.13, 122.16, 128.17, 131.61, 132.82, 133.00, 136.38, 136.49, 161.99, 197.26
p.p.m. IR (KBr): 3441(–OH), 1661 (Cδb O), 1595, 1513, 1451 (Ar, naphthalene) cm-1. Elemental analysis: Calcd for
C24H16O4; C 78.25, H 4.38. Found: C 78.10, H 4.41. m.p. = 501.4–502.1 K.
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 (Å2)
x
y
z
Uiso*/Ueq
O1
0.59530 (16)
0.33352 (16)
0.70450 (18)
0.6979
0.00535 (9)
0.08096 (8)
0.12871 (10)
0.0774
0.56238 (5)
0.70315 (5)
0.50841 (5)
0.5182
0.0397 (4)
0.0354 (3)
0.0454 (4)
0.068*
O2
O3
H3A
O4
0.28594 (17)
0.2677
0.24410 (9)
0.1908
0.72288 (5)
0.7248
0.0379 (4)
0.057*
H4A
O5
1.16664 (16)
0.88873 (16)
1.23369 (16)
1.2436
0.38740 (8)
0.33585 (9)
0.54805 (8)
0.4940
0.29072 (5)
0.43501 (5)
0.26784 (5)
0.2662
0.0343 (3)
0.0383 (4)
0.0342 (3)
0.051*
O6
O7
H7A
O8
0.78121 (16)
0.7869
0.46528 (9)
0.4129
0.47975 (5)
0.4717
0.0388 (4)
0.058*
H8A
C1
0.5552 (2)
0.6448 (2)
0.6704 (3)
0.7307
0.15430 (12)
0.18248 (13)
0.27101 (14)
0.2890
0.57795 (7)
0.54094 (7)
0.53296 (8)
0.5072
0.0261 (4)
0.0317 (5)
0.0402 (5)
0.048*
C2
C3
H3
C4
0.6088 (3)
0.6211
0.33053 (14)
0.3903
0.56218 (8)
0.5553
0.0403 (5)
0.048*
H4
C5
0.4711 (2)
0.4903
0.36949 (13)
0.4289
0.63416 (8)
0.6281
0.0374 (5)
0.045*
H5
C6
0.3910 (2)
0.3509
0.34717 (13)
0.3908
0.67298 (8)
0.6930
0.0375 (5)
0.045*
H6
C7
0.3676 (2)
0.4339 (2)
0.5044 (2)
0.5268 (2)
0.5047 (2)
0.3372 (2)
0.3004 (3)
0.3828
0.25929 (12)
0.19376 (11)
0.21635 (11)
0.30588 (12)
0.06209 (12)
0.03860 (12)
−0.04404 (14)
−0.0838
0.68344 (7)
0.65670 (7)
0.61254 (7)
0.60257 (7)
0.57486 (7)
0.57922 (7)
0.59417 (8)
0.6043
0.0301 (4)
0.0251 (4)
0.0262 (4)
0.0304 (4)
0.0281 (4)
0.0307 (4)
0.0394 (5)
0.047*
C8
C9
C10
C11
C12
C13
H13
C14
H14
C15
0.1447 (3)
0.1201
−0.06876 (18)
−0.1250
0.59444 (9)
0.6055
0.0546 (7)
0.066*
0.0249 (3)
−0.01195 (19)
0.57867 (10)
0.0622 (8)
Acta Cryst. (2013). C69, 1541-1544
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supplementary materials
H15
C16
H16
C17
H17
C18
C19
C20
H20
C21
H21
C22
H22
C23
H23
C24
H24
C25
C26
C27
H27
C28
H28
C29
H29
C30
H30
C31
C32
C33
C34
C35
C36
C37
H37
C38
H38
C39
H39
C40
H40
C41
H41
C42
C43
C44
H44
C45
H45
−0.0824
0.0608 (3)
−0.0219
−0.0291
0.5787
0.075*
0.07032 (18)
0.1092
0.56283 (11)
0.5515
0.0634 (8)
0.076*
0.2165 (3)
0.2410
0.09592 (15)
0.1527
0.56354 (9)
0.5533
0.0452 (6)
0.054*
0.4434 (2)
0.5934 (2)
0.5880 (2)
0.4893
0.10713 (11)
0.05592 (11)
−0.03217 (12)
−0.0591
0.68058 (7)
0.68426 (6)
0.69564 (7)
0.6992
0.0266 (4)
0.0256 (4)
0.0312 (4)
0.037*
0.7257 (3)
0.7212
−0.08031 (13)
−0.1405
0.70180 (7)
0.7088
0.0372 (5)
0.045*
0.8705 (3)
0.9650
−0.04107 (13)
−0.0744
0.69773 (8)
0.7018
0.0387 (5)
0.046*
0.8772 (2)
0.9764
0.04705 (13)
0.0743
0.68771 (7)
0.6856
0.0342 (5)
0.041*
0.7395 (2)
0.7445
0.09493 (12)
0.1550
0.68081 (7)
0.6736
0.0281 (4)
0.034*
1.0770 (2)
1.1526 (2)
1.1424 (2)
1.1923
0.50749 (11)
0.56839 (12)
0.65782 (12)
0.6982
0.33412 (7)
0.30663 (7)
0.31597 (7)
0.2963
0.0239 (4)
0.0270 (4)
0.0319 (5)
0.038*
1.0614 (2)
1.0491
0.68587 (12)
0.7463
0.35303 (7)
0.3578
0.0320 (5)
0.038*
0.9136 (2)
0.9099
0.65890 (13)
0.7195
0.42445 (7)
0.4301
0.0324 (5)
0.039*
0.8418 (2)
0.7822
0.60489 (13)
0.6275
0.45416 (7)
0.4789
0.0329 (5)
0.039*
0.8562 (2)
0.9476 (2)
1.0070 (2)
0.9944 (2)
1.0602 (2)
0.9068 (2)
0.9079 (2)
1.0052
0.51460 (13)
0.47933 (12)
0.53647 (11)
0.62724 (12)
0.41899 (11)
0.37078 (11)
0.28096 (12)
0.2513
0.44808 (7)
0.41317 (6)
0.37722 (6)
0.38497 (7)
0.31273 (7)
0.31184 (6)
0.30647 (7)
0.3050
0.0284 (4)
0.0249 (4)
0.0236 (4)
0.0269 (4)
0.0253 (4)
0.0253 (4)
0.0311 (4)
0.037*
0.7674 (3)
0.7686
0.23492 (13)
0.1736
0.30334 (8)
0.3006
0.0390 (5)
0.047*
0.6254 (3)
0.5290
0.27830 (14)
0.2467
0.30416 (8)
0.3019
0.0409 (5)
0.049*
0.6233 (2)
0.5255
0.36775 (14)
0.3975
0.30822 (7)
0.3082
0.0369 (5)
0.044*
0.7638 (2)
0.7623
0.41366 (12)
0.4749
0.31236 (7)
0.3156
0.0291 (4)
0.035*
0.9873 (2)
1.1500 (2)
1.1717 (3)
1.0824
0.38596 (12)
0.35211 (12)
0.26267 (13)
0.2254
0.41975 (7)
0.41585 (7)
0.41421 (8)
0.4128
0.0272 (4)
0.0267 (4)
0.0389 (5)
0.047*
1.3211 (3)
1.3345
0.22773 (14)
0.1668
0.41467 (9)
0.4132
0.0474 (6)
0.057*
Acta Cryst. (2013). C69, 1541-1544
sup-3

supplementary materials
C46
H46
C47
H47
C48
H48
1.4513 (3)
1.5543
0.28168 (15)
0.2579
0.41724 (8)
0.4172
0.0431 (5)
0.052*
1.4317 (2)
1.5216
0.37000 (14)
0.4069
0.41985 (8)
0.4221
0.0384 (5)
0.046*
1.2822 (2)
1.2698
0.40531 (12)
0.4663
0.41925 (7)
0.4212
0.0300 (4)
0.036*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
O1
0.0404 (8)
0.0376 (8)
0.0493 (9)
0.0443 (9)
0.0375 (8)
0.0404 (8)
0.0421 (8)
0.0374 (8)
0.0256 (10)
0.0307 (10)
0.0469 (13)
0.0502 (13)
0.0480 (13)
0.0468 (13)
0.0294 (10)
0.0254 (9)
0.0245 (9)
0.0340 (11)
0.0325 (11)
0.0331 (11)
0.0475 (13)
0.0574 (16)
0.0408 (14)
0.0314 (13)
0.0357 (12)
0.0322 (10)
0.0341 (10)
0.0390 (11)
0.0522 (14)
0.0414 (12)
0.0313 (11)
0.0340 (11)
0.0232 (9)
0.0270 (10)
0.0390 (11)
0.0383 (11)
0.0353 (11)
0.0291 (10)
0.0235 (10)
0.0218 (9)
0.0342 (8)
0.0319 (8)
0.0543 (10)
0.0315 (8)
0.0308 (8)
0.0361 (8)
0.0287 (7)
0.0478 (9)
0.0285 (10)
0.0401 (12)
0.0453 (13)
0.0329 (12)
0.0216 (10)
0.0255 (11)
0.0311 (11)
0.0217 (9)
0.0244 (10)
0.0254 (10)
0.0284 (10)
0.0311 (11)
0.0382 (12)
0.0649 (17)
0.086 (2)
0.0473 (9)
0.0026 (7)
0.0166 (7)
0.0186 (7)
0.0185 (7)
0.0137 (7)
0.0161 (7)
0.0132 (7)
0.0170 (6)
0.0153 (6)
0.0016 (8)
0.0022 (8)
0.0050 (10)
−0.0050 (10)
−0.0093 (10)
−0.0018 (10)
0.0012 (8)
0.0025 (8)
−0.0021 (8)
−0.0057 (9)
0.0066 (8)
0.0076 (8)
0.0079 (10)
0.0114 (12)
0.0159 (13)
0.0013 (13)
0.0021 (11)
0.0061 (8)
0.0058 (8)
0.0090 (9)
0.0065 (10)
0.0034 (10)
0.0032 (9)
0.0036 (8)
0.0031 (8)
0.0047 (8)
0.0074 (9)
0.0024 (9)
0.0010 (9)
0.0059 (9)
0.0021 (8)
0.0026 (8)
−0.0063 (7)
0.0004 (6)
−0.0065 (7)
−0.0053 (7)
−0.0012 (6)
0.0051 (7)
0.0011 (6)
O2
0.0399 (8)
0.0355 (8)
0.0401 (8)
0.0373 (8)
0.0402 (8)
0.0347 (8)
0.0336 (8)
0.0239 (9)
0.0242 (10)
0.0285 (11)
0.0357 (12)
0.0397 (12)
0.0389 (12)
0.0293 (10)
0.0282 (10)
0.0284 (10)
0.0297 (10)
0.0241 (10)
0.0289 (10)
0.0333 (11)
0.0429 (14)
0.0621 (17)
0.085 (2)
−0.0025 (6)
−0.0099 (8)
0.0052 (7)
O3
O4
O5
0.0012 (6)
O6
−0.0111 (7)
−0.0034 (6)
−0.0054 (7)
−0.0021 (8)
−0.0066 (9)
−0.0149 (10)
−0.0131 (10)
−0.0003 (9)
0.0077 (9)
O7
O8
0.0011 (7)
C1
0.0009 (8)
−0.0001 (9)
0.0080 (10)
0.0111 (10)
0.0038 (9)
−0.0049 (9)
−0.0011 (8)
−0.0009 (8)
0.0029 (8)
0.0020 (8)
−0.0012 (8)
−0.0112 (9)
−0.0061 (9)
−0.0089 (12)
−0.0271 (15)
−0.0304 (16)
−0.0127 (11)
−0.0060 (8)
−0.0008 (7)
0.0017 (8)
0.0043 (9)
0.0018 (10)
0.0001 (9)
0.0002 (8)
0.0002 (8)
0.0000 (8)
0.0034 (8)
−0.0013 (8)
−0.0065 (9)
−0.0053 (9)
0.0008 (8)
−0.0010 (8)
C2
C3
C4
C5
C6
C7
0.0032 (8)
C8
0.0000 (8)
C9
−0.0010 (8)
−0.0032 (8)
0.0006 (9)
C10
C11
C12
C13
C14
C15
C16
C17
C18
C19
C20
C21
C22
C23
C24
C25
C26
C27
C28
C29
C30
C31
C32
−0.0048 (9)
−0.0131 (10)
−0.0318 (14)
−0.0305 (15)
−0.0024 (12)
−0.0046 (10)
−0.0032 (8)
−0.0007 (8)
−0.0018 (9)
0.0057 (10)
0.0125 (10)
−0.0017 (9)
−0.0006 (8)
−0.0006 (7)
−0.0001 (8)
−0.0068 (9)
−0.0003 (8)
0.0058 (9)
0.0724 (19)
0.0396 (13)
0.0234 (10)
0.0236 (10)
0.0259 (10)
0.0248 (10)
0.0375 (12)
0.0406 (12)
0.0270 (10)
0.0229 (9)
0.0288 (10)
0.0249 (10)
0.0236 (10)
0.0313 (11)
0.0433 (12)
0.0389 (12)
0.0284 (10)
0.0596 (15)
0.0249 (10)
0.0197 (9)
0.0297 (10)
0.0350 (11)
0.0369 (12)
0.0306 (11)
0.0233 (10)
0.0257 (9)
0.0255 (10)
0.0326 (11)
0.0337 (11)
0.0302 (10)
0.0269 (10)
0.0227 (9)
0.0247 (9)
0.0052 (9)
−0.0020 (8)
−0.0020 (8)
Acta Cryst. (2013). C69, 1541-1544
sup-4

supplementary materials
C33
C34
C35
C36
C37
C38
C39
C40
C41
C42
C43
C44
C45
C46
C47
C48
0.0199 (9)
0.0269 (10)
0.0269 (10)
0.0245 (10)
0.0248 (10)
0.0290 (10)
0.0320 (11)
0.0467 (13)
0.0493 (13)
0.0297 (10)
0.0302 (10)
0.0259 (10)
0.0294 (11)
0.0327 (12)
0.0498 (14)
0.0469 (13)
0.0271 (10)
0.0235 (9)
0.0280 (10)
0.0219 (9)
0.0201 (9)
0.0272 (10)
0.0346 (11)
0.0327 (11)
0.0301 (11)
0.0247 (10)
0.0196 (9)
0.0225 (9)
0.0431 (13)
0.0543 (15)
0.0401 (13)
0.0389 (12)
0.0278 (10)
−0.0013 (8)
0.0000 (8)
0.0003 (7)
0.0014 (8)
0.0051 (8)
0.0048 (8)
0.0056 (9)
0.0067 (10)
0.0008 (10)
0.0028 (9)
0.0009 (8)
0.0041 (8)
0.0024 (8)
−0.0017 (10)
−0.0019 (12)
−0.0006 (10)
0.0011 (9)
0.0006 (9)
−0.0006 (8)
−0.0016 (8)
0.0028 (8)
0.0254 (10)
0.0299 (10)
0.0315 (10)
0.0376 (11)
0.0509 (14)
0.0427 (13)
0.0311 (11)
0.0323 (11)
0.0321 (10)
0.0317 (10)
0.0428 (13)
0.0534 (15)
0.0385 (12)
0.0289 (11)
0.0346 (11)
0.0003 (8)
−0.0031 (8)
−0.0035 (9)
−0.0110 (10)
−0.0183 (10)
−0.0018 (10)
−0.0013 (8)
−0.0077 (8)
−0.0014 (8)
−0.0040 (9)
0.0080 (11)
0.0137 (11)
−0.0005 (9)
−0.0027 (8)
−0.0017 (8)
−0.0045 (8)
−0.0033 (9)
−0.0042 (10)
−0.0019 (10)
0.0001 (8)
−0.0009 (8)
0.0023 (8)
−0.0005 (9)
−0.0057 (10)
−0.0028 (10)
0.0032 (10)
0.0016 (8)
Geometric parameters (Å, º)
O1—C11
O2—C18
O3—C2
O3—H3A
O4—C7
O4—H4A
O5—C35
O6—C42
O7—C26
O7—H7A
O8—C31
O8—H8A
C1—C2
1.238 (2)
C21—H21
0.9500
1.238 (2)
1.349 (2)
0.8400
C22—C23
C22—H22
C23—C24
C23—H23
C24—H24
C25—C26
C25—C33
C25—C35
C26—C27
C27—C28
C27—H27
C28—C34
C28—H28
C29—C30
C29—C34
C29—H29
C30—C31
C30—H30
C31—C32
C32—C33
C32—C42
C33—C34
C35—C36
C36—C41
C36—C37
C37—C38
C37—H37
C38—C39
C38—H38
C39—C40
1.390 (3)
0.9500
1.380 (3)
0.9500
1.356 (2)
0.8400
0.9500
1.237 (2)
1.244 (2)
1.354 (2)
0.8400
1.399 (3)
1.437 (2)
1.486 (2)
1.409 (3)
1.349 (3)
0.9500
1.357 (2)
0.8400
1.392 (3)
1.439 (3)
1.488 (3)
1.405 (3)
1.355 (3)
0.9500
1.414 (3)
0.9500
C1—C9
C1—C11
C2—C3
1.350 (3)
1.419 (3)
0.9500
C3—C4
C3—H3
C4—C10
C4—H4
C5—C6
1.411 (3)
0.9500
1.412 (3)
0.9500
1.397 (3)
1.445 (2)
1.488 (3)
1.424 (3)
1.500 (3)
1.386 (3)
1.395 (3)
1.385 (3)
0.9500
1.358 (3)
1.417 (3)
0.9500
C5—C10
C5—H5
C6—C7
1.405 (3)
0.9500
C6—H6
C7—C8
1.398 (3)
1.437 (3)
1.485 (3)
1.426 (3)
1.487 (3)
1.385 (3)
C8—C9
C8—C18
C9—C10
C11—C12
C12—C13
1.383 (3)
0.9500
1.386 (3)
Acta Cryst. (2013). C69, 1541-1544
sup-5

supplementary materials
C12—C17
C13—C14
C13—H13
C14—C15
C14—H14
C15—C16
C15—H15
C16—C17
C16—H16
C17—H17
C18—C19
C19—C24
C19—C20
C20—C21
C20—H20
C21—C22
1.386 (3)
1.379 (3)
0.9500
C39—H39
C40—C41
C40—H40
C41—H41
C42—C43
C43—C48
C43—C44
C44—C45
C44—H44
C45—C46
C45—H45
C46—C47
C46—H46
C47—C48
C47—H47
C48—H48
0.9500
1.383 (3)
0.9500
1.377 (4)
0.9500
0.9500
1.493 (3)
1.387 (3)
1.395 (3)
1.379 (3)
0.9500
1.386 (4)
0.9500
1.380 (3)
0.9500
0.9500
1.381 (3)
0.9500
1.495 (3)
1.393 (3)
1.397 (3)
1.381 (3)
0.9500
1.377 (3)
0.9500
1.382 (3)
0.9500
1.388 (3)
0.9500
C2—O3—H3A
C7—O4—H4A
C26—O7—H7A
C31—O8—H8A
C2—C1—C9
C2—C1—C11
C9—C1—C11
O3—C2—C1
O3—C2—C3
C1—C2—C3
C4—C3—C2
C4—C3—H3
C2—C3—H3
C3—C4—C10
C3—C4—H4
C10—C4—H4
C6—C5—C10
C6—C5—H5
C10—C5—H5
C5—C6—C7
C5—C6—H6
C7—C6—H6
O4—C7—C8
O4—C7—C6
C8—C7—C6
C7—C8—C9
C7—C8—C18
C9—C8—C18
C10—C9—C8
C10—C9—C1
C8—C9—C1
C4—C10—C5
109.5
C23—C24—H24
C19—C24—H24
C26—C25—C33
C26—C25—C35
C33—C25—C35
O7—C26—C25
O7—C26—C27
C25—C26—C27
C28—C27—C26
C28—C27—H27
C26—C27—H27
C27—C28—C34
C27—C28—H28
C34—C28—H28
C30—C29—C34
C30—C29—H29
C34—C29—H29
C29—C30—C31
C29—C30—H30
C31—C30—H30
O8—C31—C32
O8—C31—C30
C32—C31—C30
C31—C32—C33
C31—C32—C42
C33—C32—C42
C34—C33—C25
C34—C33—C32
C25—C33—C32
C28—C34—C29
C28—C34—C33
C29—C34—C33
119.7
109.5
119.7
109.5
118.50 (16)
116.21 (16)
124.92 (16)
123.97 (17)
114.41 (16)
121.54 (17)
119.67 (17)
120.2
109.5
119.10 (17)
115.86 (16)
124.69 (16)
123.45 (18)
115.02 (17)
121.41 (18)
119.62 (19)
120.2
120.2
121.43 (18)
119.3
120.2
121.60 (19)
119.2
119.3
121.54 (18)
119.2
119.2
121.30 (18)
119.3
119.2
119.41 (18)
120.3
119.4
119.68 (19)
120.2
120.3
122.84 (18)
115.40 (17)
121.71 (17)
118.57 (17)
115.64 (16)
125.53 (16)
118.09 (16)
117.69 (16)
124.22 (16)
120.01 (17)
119.92 (17)
120.06 (17)
120.2
123.51 (17)
114.94 (17)
121.41 (18)
118.88 (17)
115.65 (16)
124.97 (16)
117.98 (17)
117.86 (17)
124.16 (16)
120.37 (18)
Acta Cryst. (2013). C69, 1541-1544
sup-6

supplementary materials
C4—C10—C9
119.71 (18)
119.88 (18)
118.62 (17)
120.57 (17)
120.18 (16)
119.67 (19)
119.78 (18)
120.21 (18)
120.3 (2)
119.9
O5—C35—C25
O5—C35—C36
C25—C35—C36
C41—C36—C37
C41—C36—C35
C37—C36—C35
C38—C37—C36
C38—C37—H37
C36—C37—H37
C39—C38—C37
C39—C38—H38
C37—C38—H38
C38—C39—C40
C38—C39—H39
C40—C39—H39
C41—C40—C39
C41—C40—H40
C39—C40—H40
C40—C41—C36
C40—C41—H41
C36—C41—H41
O6—C42—C32
O6—C42—C43
C32—C42—C43
C48—C43—C44
C48—C43—C42
C44—C43—C42
C45—C44—C43
C45—C44—H44
C43—C44—H44
C44—C45—C46
C44—C45—H45
C46—C45—H45
C47—C46—C45
C47—C46—H46
C45—C46—H46
C46—C47—C48
C46—C47—H47
C48—C47—H47
C47—C48—C43
C47—C48—H48
C43—C48—H48
120.45 (16)
118.50 (16)
120.63 (16)
119.49 (17)
121.66 (16)
118.66 (17)
120.10 (19)
119.9
C5—C10—C9
O1—C11—C12
O1—C11—C1
C12—C11—C1
C13—C12—C17
C13—C12—C11
C17—C12—C11
C14—C13—C12
C14—C13—H13
C12—C13—H13
C15—C14—C13
C15—C14—H14
C13—C14—H14
C14—C15—C16
C14—C15—H15
C16—C15—H15
C17—C16—C15
C17—C16—H16
C15—C16—H16
C16—C17—C12
C16—C17—H17
C12—C17—H17
O2—C18—C8
119.9
119.92 (19)
120.0
119.9
120.0 (2)
120.0
120.0
120.19 (19)
119.9
120.0
120.0 (2)
120.0
119.9
119.93 (19)
120.0
120.0
120.1 (2)
119.9
120.0
120.32 (18)
119.8
119.9
119.9 (2)
120.1
119.8
119.38 (17)
117.92 (17)
122.08 (15)
118.68 (18)
122.54 (17)
118.39 (17)
120.8 (2)
119.6
120.1
120.07 (17)
118.57 (16)
120.77 (16)
119.16 (17)
121.83 (16)
118.79 (17)
120.20 (19)
119.9
O2—C18—C19
C8—C18—C19
C24—C19—C20
C24—C19—C18
C20—C19—C18
C21—C20—C19
C21—C20—H20
C19—C20—H20
C20—C21—C22
C20—C21—H21
C22—C21—H21
C21—C22—C23
C21—C22—H22
C23—C22—H22
C24—C23—C22
C24—C23—H23
C22—C23—H23
C23—C24—C19
119.6
119.8 (2)
120.1
119.9
120.19 (19)
119.9
120.1
120.0 (2)
120.0
119.9
119.90 (19)
120.0
120.0
120.4 (2)
119.8
120.0
119.95 (19)
120.0
119.8
120.31 (19)
119.8
120.0
120.56 (18)
119.8
C9—C1—C2—O3
C11—C1—C2—O3
C9—C1—C2—C3
C11—C1—C2—C3
O3—C2—C3—C4
C1—C2—C3—C4
176.55 (17)
−9.9 (3)
C33—C25—C26—O7
C35—C25—C26—O7
C33—C25—C26—C27
C35—C25—C26—C27
O7—C26—C27—C28
C25—C26—C27—C28
174.45 (16)
−12.2 (3)
−9.1 (3)
−7.7 (3)
165.83 (18)
176.95 (19)
0.9 (3)
164.32 (17)
178.54 (18)
1.7 (3)
Acta Cryst. (2013). C69, 1541-1544
sup-7

supplementary materials
C2—C3—C4—C10
C10—C5—C6—C7
C5—C6—C7—O4
3.8 (3)
C26—C27—C28—C34
4.0 (3)
2.5 (3)
C34—C29—C30—C31
C29—C30—C31—O8
C29—C30—C31—C32
O8—C31—C32—C33
C30—C31—C32—C33
O8—C31—C32—C42
C30—C31—C32—C42
C26—C25—C33—C34
C35—C25—C33—C34
C26—C25—C33—C32
C35—C25—C33—C32
C31—C32—C33—C34
C42—C32—C33—C34
C31—C32—C33—C25
C42—C32—C33—C25
C27—C28—C34—C29
C27—C28—C34—C33
C30—C29—C34—C28
C30—C29—C34—C33
C25—C33—C34—C28
C32—C33—C34—C28
C25—C33—C34—C29
C32—C33—C34—C29
C26—C25—C35—O5
C33—C25—C35—O5
C26—C25—C35—C36
C33—C25—C35—C36
O5—C35—C36—C41
C25—C35—C36—C41
O5—C35—C36—C37
C25—C35—C36—C37
C41—C36—C37—C38
C35—C36—C37—C38
C36—C37—C38—C39
C37—C38—C39—C40
C38—C39—C40—C41
C39—C40—C41—C36
C37—C36—C41—C40
C35—C36—C41—C40
C31—C32—C42—O6
C33—C32—C42—O6
C31—C32—C42—C43
C33—C32—C42—C43
O6—C42—C43—C48
C32—C42—C43—C48
O6—C42—C43—C44
C32—C42—C43—C44
C48—C43—C44—C45
4.3 (3)
−179.88 (18)
4.2 (3)
179.54 (17)
2.3 (3)
C5—C6—C7—C8
O4—C7—C8—C9
173.87 (17)
−10.5 (3)
−13.8 (3)
161.77 (18)
10.1 (3)
172.72 (16)
−10.2 (3)
−12.8 (3)
164.26 (17)
10.5 (3)
C6—C7—C8—C9
O4—C7—C8—C18
C6—C7—C8—C18
C7—C8—C9—C10
C18—C8—C9—C10
C7—C8—C9—C1
−161.39 (17)
−170.43 (17)
18.0 (3)
−162.23 (17)
−169.88 (17)
17.4 (3)
C18—C8—C9—C1
C2—C1—C9—C10
C11—C1—C9—C10
C2—C1—C9—C8
9.7 (3)
11.4 (2)
−163.18 (17)
−169.70 (17)
17.4 (3)
−162.44 (17)
−168.17 (17)
18.0 (3)
C11—C1—C9—C8
C3—C4—C10—C5
C3—C4—C10—C9
C6—C5—C10—C4
C6—C5—C10—C9
C8—C9—C10—C4
C1—C9—C10—C4
C8—C9—C10—C5
C1—C9—C10—C5
C2—C1—C11—O1
C9—C1—C11—O1
C2—C1—C11—C12
C9—C1—C11—C12
O1—C11—C12—C13
C1—C11—C12—C13
O1—C11—C12—C17
C1—C11—C12—C17
C17—C12—C13—C14
C11—C12—C13—C14
C12—C13—C14—C15
C13—C14—C15—C16
C14—C15—C16—C17
C15—C16—C17—C12
C13—C12—C17—C16
C11—C12—C17—C16
C7—C8—C18—O2
C9—C8—C18—O2
C7—C8—C18—C19
C9—C8—C18—C19
O2—C18—C19—C24
C8—C18—C19—C24
O2—C18—C19—C20
C8—C18—C19—C20
C24—C19—C20—C21
176.50 (19)
−1.5 (3)
178.29 (18)
−2.2 (3)
179.50 (19)
−2.6 (3)
176.80 (18)
−2.7 (3)
174.14 (17)
−5.3 (3)
−5.1 (3)
175.24 (17)
174.34 (17)
−5.3 (3)
−3.8 (3)
176.71 (17)
39.0 (3)
37.0 (3)
−147.85 (19)
−131.72 (18)
41.4 (3)
−150.10 (18)
−135.40 (17)
37.5 (3)
32.3 (3)
−147.62 (18)
24.9 (3)
−156.76 (17)
−141.0 (2)
29.9 (3)
27.4 (2)
−160.11 (17)
−2.1 (3)
−1.3 (3)
−174.66 (19)
1.6 (3)
−177.20 (17)
1.8 (3)
−0.4 (4)
−0.1 (3)
−1.0 (4)
−1.2 (3)
1.3 (4)
0.8 (3)
−0.1 (3)
0.8 (3)
173.2 (2)
39.3 (3)
175.74 (17)
35.6 (2)
−148.98 (18)
−131.77 (18)
40.0 (3)
−150.32 (18)
−135.17 (18)
38.9 (3)
−150.29 (18)
20.9 (3)
−153.20 (18)
17.7 (3)
24.2 (3)
19.6 (3)
−164.63 (17)
−2.0 (3)
−169.47 (17)
−1.6 (3)
Acta Cryst. (2013). C69, 1541-1544
sup-8

supplementary materials
C18—C19—C20—C21
C19—C20—C21—C22
C20—C21—C22—C23
C21—C22—C23—C24
C22—C23—C24—C19
C20—C19—C24—C23
C18—C19—C24—C23
−176.70 (17)
1.3 (3)
C42—C43—C44—C45
−174.72 (19)
0.6 (3)
C43—C44—C45—C46
C44—C45—C46—C47
C45—C46—C47—C48
C46—C47—C48—C43
C44—C43—C48—C47
C42—C43—C48—C47
0.4 (3)
0.7 (3)
−1.3 (3)
0.6 (3)
−0.9 (3)
−0.2 (3)
1.4 (3)
1.1 (3)
175.56 (16)
174.21 (17)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
O3—H3A···O1
O4—H4A···O2
O4—H4A···O5i
O7—H7A···O2ii
O7—H7A···O5
O8—H8A···O6
C3—H3···O6
0.84
0.84
0.84
0.84
0.84
0.84
0.95
0.95
1.91
1.90
2.39
2.26
1.92
1.83
2.59
2.57
2.631 (2)
2.616 (2)
2.989 (2)
2.843 (2)
2.635 (2)
2.557 (2)
3.542 (3)
3.401 (3)
143
142
129
126
143
144
178
146
C21—H21···O4iii
Symmetry codes: (i) x−1, −y+1/2, z+1/2; (ii) x+1, −y+1/2, z−1/2; (iii) −x+1, y−1/2, −z+3/2.
Acta Cryst. (2013). C69, 1541-1544
sup-9

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