1,7-Dimethyl-penta-cyclo-[5.4.0.0.0.0]undecane-8,11-dione.

Abstract

The structure of the title compound, C(13)H(14)O(2), a penta-cyclo-undecane cage derivative, exhibits unusual Csp(3)-Csp(3) single-bond lengths ranging from 1.505 (3) to 1.607 (2) Å and strained bond angles as small as 88.7 (1)° and as large as 121.0 (2)°. In this meso compound, an inter-nal non-crystallographic mirror plane exists, bis-ecting the mol-ecule. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into an infinite spiral about a twofold screw axis along the [100] direction.

Full text

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1,7-Dimethylpentacyclo[5.4.0.02,6.-
03,10.05,9]undecane-8,11-dione
Sai Kumar Chakka,aOluseye K. Onajole,aThavendran
Govender,bGlenn E. M. Maguire,a* Hong Sucand
Hendrik G. Krugera
aSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa,
bSchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban
4000, South Africa, andcSchool of Chemistry, University of Cape Town, South Africa
Correspondence e-mail: maguireg@ukzn.ac.za
Received 18 June 2010; accepted 25 June 2010
Key indicators: single-crystal X-ray study; T = 173 K; mean ?(C–C) = 0.002 A ˚;
R factor = 0.033; wR factor = 0.090; data-to-parameter ratio = 7.7.
The structure of the title compound, C13H14O2, a pentacyclo-
undecane cage derivative, exhibits unusual Csp3—Csp3single-
bond lengths ranging from 1.505 (3) to 1.607 (2) A˚
strained bond angles as small as 88.7 (1)?and as large as
121.0 (2)?. In this meso compound, an internal non-crystal-
lographic mirror plane exists, bisecting the molecule. In the
crystal, weak C—H???O hydrogen bonds link the molecules
into an infinite spiral about a twofold screw axis along the
[100] direction.
and
Related literature
For related literature and examples of PCU cage structures
exhibiting C—C bond lengths that deviate from the norm, see:
Flippen-Anderson et al. (1991); Bott et al. (1998); Linden et al.
(2005); Kruger et al. (2006). For the crystal packing of analo-
gous PCU cage structures, see: Kruger et al. (2006); Boyle et al.
(2007a,b). For the synthesis, see: Mehta et al. (1981). For
hydrogen bonding, see: Desiraju et al. (1999).
Experimental
Crystal data
C13H14O2
Mr= 202.24
Orthorhombic, P212121
a = 7.7914 (2) A˚
b = 8.2149 (3) A˚
c = 15.4830 (5) A˚
V = 991.00 (5) A˚3
Z = 4
Cu K? radiation
? = 0.72 mm?1
T = 173 K
0.32 ? 0.25 ? 0.21 mm
Data collection
Bruker Kappa DUO APEXII
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
Tmin= 0.702, Tmax= 0.753
4922 measured reflections
1055 independent reflections
1044 reflections with I > 2?(I)
Rint= 0.020
Refinement
R[F2> 2?(F2)] = 0.033
wR(F2) = 0.090
S = 1.06
1055 reflections
137 parameters
H-atom parameters constrained
??max= 0.21 e A˚?3
??min= ?0.18 e A˚?3
Table 1
Selected bond lengths (A˚).
C1—C2
C1—C7
C2—C3
C2—C6
C3—C4
C3—C8
C4—C5
C5—C12
C5—C6
1.525 (3)
1.529 (2)
1.546 (2)
1.549 (2)
1.515 (3)
1.587 (2)
1.520 (2)
1.519 (2)
1.560 (2)
C5—C10
C6—C11
C7—C8
C7—C11
C8—C9
C9—C10
C10—C13
C10—C11
1.607 (2)
1.551 (3)
1.549 (2)
1.553 (3)
1.515 (3)
1.523 (3)
1.505 (3)
1.560 (2)
Table 2
Hydrogen-bond geometry (A˚,?).
D—H???A
C2—H2???O2i
C3—H3???O2ii
Symmetry codes: (i) x ? 1;y;z; (ii) x ?1
D—HH???AD???AD—H???A
1.00
1.00
2.58
2.59
3.303 (2)
3.335 (2)
129
131
2;?y þ3
2;?z þ 1.
Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT
(Bruker, 2006); data reduction: SAINT; program(s) used to solve
structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine
structure: SHELXL97(Sheldrick,
ORTEP-3 (Farrugia, 1997); software used to prepare material for
publication: SHELXL97.
2008); moleculargraphics:
This work was supported by grants from the National
Research Foundation (South Africa), GUN 2046819, and the
University of KwaZulu-Natal.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: HB5509).
References
Bott, S. G., Marchand, A. P., Alihodzic, S. & Kumar, K. A. (1998). J. Chem.
Crystallogr. 28, 251–258.
Boyle, G. A., Govender, T., Karpoormath, R. & Kruger, H. G. (2007a). Acta
Cryst. E63, o3977.
Boyle, G. A., Govender, T., Karpoormath, R. & Kruger, H. G. (2007b). Acta
Cryst. E63, o4797.
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,
USA.
organic compounds
Acta Cryst. (2010). E66, o1901–o1902doi:10.1107/S1600536810025055 Chakka et al.
o1901
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond In Structural
Chemistry and Biology. IUCr Monographs on Crystallography. Oxford
University Press.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Flippen-Anderson, J. L., George, C., Gilardi, R., Zajac, W. W., Walters, T. R.,
Marchand, A., Dave, P. R. & Arney, B. E. (1991). Acta Cryst. C47, 813–817.
Kruger, H. G., Rademeyer, M. & Ramdhani, R. (2006). Acta Cryst. E62, o268–
o270.
Linden, A., Roman ´ski, J., Mloston ´, G. & Heimgartner, H. (2005). Acta Cryst.
C61, o221–o226.
Mehta, G., Srikrishna, A., Reddy, A. V. & Nair, M. S. (1981). Tetrahedron, 37,
4543–4559.
Sheldrick, G. M. (1997). SADABS. University of Go ¨ttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
organic compounds
o1902
Chakka et al.
? C13H14O2
Acta Cryst. (2010). E66, o1901–o1902

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supplementary materials
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Acta Cryst. (2010). E66, o1901-o1902 [ doi:10.1107/S1600536810025055 ]
1,7-Dimethylpentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione
S. K. Chakka, O. K. Onajole, T. Govender, G. E. M. Maguire, H. Su and H. G. Kruger
Comment
As part of an ongoing study of the crystal structures and chemical reactivity of polycyclic pentacycloundecane (PCU) cage
derivatives, the structure of the title compound, (I), was obtained (Scheme 1). Although the compound is known (Mehta et
al., 1981), its crystal structure has not been reported. Previous studies showed that PCU cage derivatives normally display
C—C bond lengths which deviate from the expected value of 1.54 Å (see related literature). Similar phenomneon on the
C—C bond lengths for this structure is observed, as the lengths of 17 Csp3—Csp3 single bonds range from 1.505 (3) Å to
1.607 (2) Å, with the bond between C10—C13 being the shortest, while that between C5—C10 is the longest (see Table
1). The labelling scheme and molecular structure is presented in Figure 1. The atoms C5, C6, C11 and C10 form a slightly
irregular square with r.m.s. deviation of fitted atoms 0.0007 Å and is a very strained system. The tetrahedral bond angles
around C10 are the most strained with the smallest angle of 88.7 (1)° (C5—C10—C11) and the biggest angle of 121.0 (2)°
(C11—C10—C13), deviating from the ideal tetrahedral angle of 109.5°. Other selected carbon atoms, which define the cage
conformation and which are coplanar with r.m.s. deviation of the fitted atoms smaller than 0.01 Å, are the following (with
r.m.s. deviation of the fitted atoms in bracket): C10, C5, C4 and C9 (0.0034 Å); C4, C9, C8 and C3 (0.0010 Å); C3, C8,
C7 and C2 (0.0019 Å); C2, C7, C11 and C6 (0.0004 Å). In the molecule of this meso compound an internal mirror plane
exists, bisecting C1 and the middle points of bonds C8—C3, C11—C6 and C10—C5. We noted a number of weak hydrogen
bonds of the type C—H···O=C presented in this structure (Desiraju et al., 1999) (see Table 2). The molecules form a infinite
right-hand spiral about a two fold screw-axis along the [100] direction via hydrogen bond C3—H3···O2 (see Figure 2).
Experimental
In a 250 ml round-bottomed flask covered with tin foil was placed 2,3-dimethyl hydroquinone (4.00 g, 0.03 mmol), sodium
chlorate (1.73 g, 0.01 mmol), 2% H2SO4 (36 ml) and 50 mg of vanadium pentoxide (catalyst). The mixture was stirred
overnight, and the product, 2,3-dimethylbenzoquinone, was extracted with dichloromethane, dried over sodium sulfate,
filtered and the filterate concentrated in vacuo to obtain 3.00 g (76%). To a vigorously stirring solution of the dried product
(3.00 g, 0.02 mmol) in toluene (12 ml) cooled to 273 K, freshly cracked cyclopentadiene (1.67 g, 0.025 mmol) was added.
The mixture was kept at 273 K for 4 h, after which the solution was allowed to attain ambient temperature over night. The
solution was poured into an evaporating dish and placed in a fumehood to evaporate the toluene, yielding the adduct as a
crude brown oil (4.20 g). Without further purification, the material was dissolved in ethyl acetate and exposed to sunlight
until a clear solution was obtained (two weeks). The solvent was removed in vacuo to obtain a crude product, which was
purified on silica gel, using a mobile phase of 6:4 hexane/ethyl acetate. The title compound was obtained as a pure white
crystalline solid (3.20 g, 72%), mp 381–382 K. 1H NMR [CDCl3, 400 MHz]: δ = 0.99 (s, 6 H, CH3), 1.85 (d, 1 H, J= 11.2
Hz, CH2), 1.99 (d, 1 H, J= 11.1 Hz, CH2), 2.68 (s, 2 H, CH), 2.73 (s, 2 H, CH), 2.81 (s, 2 H, CH). 13C NMR [CDCl3, 100
MHz]: δ = 11.4 (q), 41.1 (t), 43.3 (d), 44.2 (d), 54.7 (d), 213.8 (s). IR (ATR): 2958, 1741, 1453,1282, 1073, 1023, 903, 869,
660 and 457 cm-1. Colourless prisms of (I) were grown by slow evaporation of a solution of the title compound in methanol,
at ambient temperature. The synthesis is summarised in Fig. 3.

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Refinement
The locations of the hydrogen atoms were found in a difference map and then positioned geometrically and allowed to
ride on their respective parent atoms, with C—H bond lengths of 1.00 (CH), 0.99 (CH2), or 0.98 (CH3). They were then
refined with a riding model with Uiso(H) = 1.5Ueq(CH3) and Uiso(H) = 1.2Ueq(X) for X = CH or CH2. When the data
were unmerged, the Flack absolute structure parameter refined to -0.07 with s.u. 0.25. Because of the large s.u., in the final
refinement, the Friedel pairs were merged.
Figures
Fig. 1. View of the molecular structure of (I) with non-H atoms drawn with 40% probability
displacement ellipsoids and H atoms are shown as open circles.
Fig. 2. Projection viewed down the b axis of (I) showing the spirals up along the 2-fold screw
axis in the [100] direction. Both the weak hydrogen bonds C3—H3···O2 and C2—H2···O2 are
shown as dotted lines. All hydrogen atoms except H2 and H3 are omitted for clarity.
Fig. 3. Preparation scheme for (I)
1,7-Dimethylpentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione
Crystal data
C13H14O2
Dx = 1.356 Mg m−3
Melting point: 382 K
Cu Kα radiation, λ = 1.54184 Å
Cell parameters from 4922 reflections
θ = 5.7–68.4°
µ = 0.72 mm−1
T = 173 K
Mr = 202.24
Orthorhombic, P212121
Hall symbol: P 2ac 2ab
a = 7.7914 (2) Å
b = 8.2149 (3) Å
c = 15.4830 (5) Å

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V = 991.00 (5) Å3
Z = 4
F(000) = 432
Prism, colourless
0.32 × 0.25 × 0.21 mm
Data collection
Bruker Kappa DUO APEXII
diffractometer
Radiation source: fine-focus sealed tube
graphite
0.5° φ scans and ω scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
Tmin = 0.702, Tmax = 0.753
4922 measured reflections
1055 independent reflections
1044 reflections with I > 2σ(I)
Rint = 0.020
θmax = 68.4°, θmin = 5.7°
h = −9→9
k = −9→9
l = −18→13
Refinement
Refinement on F2
Secondary atom site location: difference Fourier map
Least-squares matrix: full
Hydrogen site location: inferred from neighbouring
sites
R[F2 > 2σ(F2)] = 0.033
H-atom parameters constrained
wR(F2) = 0.090
w = 1/[σ2(Fo2) + (0.0627P)2 + 0.1901P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.21 e Å−3
Δρmin = −0.18 e Å−3
Extinction correction: SHELXL97 (Sheldrick, 2008),
Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Extinction coefficient: 0.0178 (18)
S = 1.06
1055 reflections
137 parameters
0 restraints
0 constraints
Primary atom site location: structure-invariant direct
methods
Special details
Experimental. Half sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 30 mm; combina-
tion of φ and ω scans of 0.5°, 40 s per °, 2 iterations.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance mat-
rix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations
between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of
cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, convention-
al 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.

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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
0.7584 (2)
0.4669 (2)
0.4395
0.3858
1.05692 (19)
0.4768 (2)
0.3674
0.6306 (2)
0.5988
0.7082 (2)
0.7092 (2)
0.5531 (2)
0.4697
0.6546 (2)
0.6912
0.7553 (2)
0.7872
0.9079 (2)
0.8361 (2)
0.6756 (2)
0.6630
0.7267 (3)
0.7260
0.6306
0.8350
0.9672 (3)
0.9104
1.0541
1.0223
y
0.32372 (19)
0.6969 (2)
0.7912
0.6915
0.5921 (2)
0.5374 (2)
0.5019
0.5612 (2)
0.6088
0.3924 (2)
0.3279 (2)
0.4167 (2)
0.3474
0.6948 (2)
0.7889
0.6726 (2)
0.7772
0.5714 (2)
0.4397 (2)
0.5243 (2)
0.5181
0.1443 (2)
0.1133
0.0915
0.1096
0.3567 (3)
0.2740
0.3046
0.4374
z
0.54950 (9)
0.36778 (12)
0.4051
0.3187
0.41443 (11)
0.41804 (11)
0.4461
0.47985 (11)
0.5371
0.48546 (12)
0.39345 (12)
0.35149 (12)
0.3190
0.33893 (11)
0.3023
0.42436 (12)
0.4532
0.39604 (12)
0.33708 (11)
0.29697 (11)
0.2328
0.38573 (13)
0.3246
0.4154
0.4122
0.28080 (13)
0.2452
0.3172
0.2433
Uiso*/Ueq
0.0395 (4)
0.0255 (4)
0.031*
0.031*
0.0381 (4)
0.0233 (4)
0.028*
0.0232 (4)
0.028*
0.0251 (4)
0.0229 (4)
0.0231 (4)
0.028*
0.0224 (4)
0.027*
0.0229 (4)
0.027*
0.0248 (4)
0.0231 (4)
0.0230 (4)
0.028*
0.0316 (5)
0.047*
0.047*
0.047*
0.0334 (5)
0.050*
0.050*
0.050*
O1
C1
H1A
H1B
O2
C2
H2
C3
H3
C4
C5
C6
H6
C7
H7
C8
H8
C9
C10
C11
H11
C12
H12A
H12B
H12C
C13
H13A
H13B
H13C
Atomic displacement parameters (Å2)
U11
0.0546 (10)
0.0229 (9)
0.0216 (7)
0.0193 (8)
0.0255 (8)
0.0250 (8)
0.0237 (9)
0.0218 (8)
0.0231 (9)
0.0227 (8)
0.0224 (9)
U22
0.0372 (8)
0.0265 (9)
0.0364 (8)
0.0247 (9)
0.0245 (9)
0.0264 (9)
0.0195 (9)
0.0240 (9)
0.0208 (8)
0.0201 (8)
0.0241 (9)
U33
0.0267 (7)
0.0269 (9)
0.0564 (10)
0.0259 (8)
0.0195 (8)
0.0240 (8)
0.0256 (9)
0.0235 (8)
0.0232 (8)
0.0257 (9)
0.0280 (9)
U12
0.0111 (8)
0.0046 (7)
−0.0003 (6)
0.0007 (7)
0.0020 (8)
0.0009 (8)
−0.0004 (7)
−0.0016 (8)
−0.0001 (8)
−0.0009 (8)
−0.0012 (8)
U13
−0.0061 (7)
−0.0001 (7)
−0.0065 (7)
0.0027 (7)
0.0024 (7)
0.0010 (7)
0.0012 (7)
−0.0017 (7)
−0.0001 (7)
−0.0029 (8)
0.0004 (7)
U23
0.0058 (6)
0.0022 (8)
−0.0079 (7)
0.0016 (7)
−0.0010 (7)
0.0017 (7)
−0.0011 (7)
−0.0019 (7)
0.0032 (7)
−0.0014 (7)
0.0030 (7)
O1
C1
O2
C2
C3
C4
C5
C6
C7
C8
C9

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C10
C11
C12
C13
0.0215 (9)
0.0236 (9)
0.0421 (11)
0.0315 (11)
0.0240 (9)
0.0255 (9)
0.0204 (9)
0.0344 (11)
0.0237 (8)
0.0200 (8)
0.0324 (9)
0.0344 (9)
0.0016 (8)
0.0001 (8)
0.0009 (9)
0.0057 (9)
0.0023 (7)
−0.0001 (7)
0.0015 (9)
0.0092 (9)
−0.0003 (7)
−0.0013 (7)
−0.0011 (7)
−0.0020 (9)
Geometric parameters (Å, °)
O1—C4
C1—C2
C1—C7
C1—H1A
C1—H1B
O2—C9
C2—C3
C2—C6
C2—H2
C3—C4
C3—C8
C3—H3
C4—C5
C5—C12
C5—C6
C5—C10
C6—C11
1.206 (2)
1.525 (3)
1.529 (2)
0.9900
0.9900
1.207 (3)
1.546 (2)
1.549 (2)
1.0000
1.515 (3)
1.587 (2)
1.0000
1.520 (2)
1.519 (2)
1.560 (2)
1.607 (2)
1.551 (3)
C6—H6
C7—C8
C7—C11
C7—H7
C8—C9
C8—H8
C9—C10
C10—C13
C10—C11
C11—H11
C12—H12A
C12—H12B
C12—H12C
C13—H13A
C13—H13B
C13—H13C
1.0000
1.549 (2)
1.553 (3)
1.0000
1.515 (3)
1.0000
1.523 (3)
1.505 (3)
1.560 (2)
1.0000
0.9800
0.9800
0.9800
0.9800
0.9800
0.9800
C2—C1—C7
C2—C1—H1A
C7—C1—H1A
C2—C1—H1B
C7—C1—H1B
H1A—C1—H1B
C1—C2—C3
C1—C2—C6
C3—C2—C6
C1—C2—H2
C3—C2—H2
C6—C2—H2
C4—C3—C2
C4—C3—C8
C2—C3—C8
C4—C3—H3
C2—C3—H3
C8—C3—H3
O1—C4—C3
O1—C4—C5
C3—C4—C5
C12—C5—C4
C12—C5—C6
C4—C5—C6
C12—C5—C10
95.26 (14)
112.7
112.7
112.7
112.7
110.2
104.26 (15)
103.29 (14)
101.25 (14)
115.4
115.4
115.4
103.24 (14)
108.33 (14)
102.26 (13)
114.0
114.0
114.0
127.20 (18)
127.29 (18)
105.51 (15)
114.86 (16)
120.11 (16)
102.91 (15)
117.97 (16)
C1—C7—H7
C8—C7—H7
C11—C7—H7
C9—C8—C7
C9—C8—C3
C7—C8—C3
C9—C8—H8
C7—C8—H8
C3—C8—H8
O2—C9—C8
O2—C9—C10
C8—C9—C10
C13—C10—C9
C13—C10—C11
C9—C10—C11
C13—C10—C5
C9—C10—C5
C11—C10—C5
C6—C11—C7
C6—C11—C10
C7—C11—C10
C6—C11—H11
C7—C11—H11
C10—C11—H11
C5—C12—H12A
115.5
115.5
115.5
102.44 (14)
108.72 (15)
102.71 (14)
113.9
113.9
113.9
127.53 (19)
126.49 (19)
105.96 (15)
114.82 (16)
121.02 (15)
102.51 (14)
118.23 (16)
107.86 (14)
88.69 (13)
102.81 (13)
91.31 (13)
108.66 (14)
116.8
116.8
116.8
109.5

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supplementary materials
sup-6
C4—C5—C10
C6—C5—C10
C2—C6—C11
C2—C6—C5
C11—C6—C5
C2—C6—H6
C11—C6—H6
C5—C6—H6
C1—C7—C8
C1—C7—C11
C8—C7—C11
108.24 (14)
89.23 (13)
103.48 (14)
108.76 (14)
90.77 (13)
116.8
116.8
116.8
103.67 (14)
103.47 (15)
101.38 (14)
C5—C12—H12B
H12A—C12—H12B
C5—C12—H12C
H12A—C12—H12C
H12B—C12—H12C
C10—C13—H13A
C10—C13—H13B
H13A—C13—H13B
C10—C13—H13C
H13A—C13—H13C
H13B—C13—H13C
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
C7—C1—C2—C3
C7—C1—C2—C6
C1—C2—C3—C4
C6—C2—C3—C4
C1—C2—C3—C8
C6—C2—C3—C8
C2—C3—C4—O1
C8—C3—C4—O1
C2—C3—C4—C5
C8—C3—C4—C5
O1—C4—C5—C12
C3—C4—C5—C12
O1—C4—C5—C6
C3—C4—C5—C6
O1—C4—C5—C10
C3—C4—C5—C10
C1—C2—C6—C11
C3—C2—C6—C11
C1—C2—C6—C5
C3—C2—C6—C5
C12—C5—C6—C2
C4—C5—C6—C2
C10—C5—C6—C2
C12—C5—C6—C11
C4—C5—C6—C11
C10—C5—C6—C11
C2—C1—C7—C8
C2—C1—C7—C11
C1—C7—C8—C9
C11—C7—C8—C9
C1—C7—C8—C3
C11—C7—C8—C3
C4—C3—C8—C9
C2—C3—C8—C9
C4—C3—C8—C7
52.94 (15)
−52.54 (16)
−145.63 (14)
−38.63 (17)
−33.19 (16)
73.81 (15)
−136.5 (2)
115.6 (2)
43.41 (18)
−64.51 (17)
18.7 (3)
−161.21 (16)
151.1 (2)
−28.88 (18)
−115.4 (2)
64.62 (18)
33.43 (17)
−74.33 (16)
128.94 (15)
21.18 (17)
133.27 (18)
4.12 (18)
−104.42 (15)
−122.20 (18)
108.64 (14)
0.10 (12)
−52.87 (16)
52.62 (15)
146.37 (15)
39.30 (17)
33.62 (18)
−73.44 (16)
0.2 (2)
−108.38 (15)
108.24 (16)
C2—C3—C8—C7
C7—C8—C9—O2
C3—C8—C9—O2
C7—C8—C9—C10
C3—C8—C9—C10
O2—C9—C10—C13
C8—C9—C10—C13
O2—C9—C10—C11
C8—C9—C10—C11
O2—C9—C10—C5
C8—C9—C10—C5
C12—C5—C10—C13
C4—C5—C10—C13
C6—C5—C10—C13
C12—C5—C10—C9
C4—C5—C10—C9
C6—C5—C10—C9
C12—C5—C10—C11
C4—C5—C10—C11
C6—C5—C10—C11
C2—C6—C11—C7
C5—C6—C11—C7
C2—C6—C11—C10
C5—C6—C11—C10
C1—C7—C11—C6
C8—C7—C11—C6
C1—C7—C11—C10
C8—C7—C11—C10
C13—C10—C11—C6
C9—C10—C11—C6
C5—C10—C11—C6
C13—C10—C11—C7
C9—C10—C11—C7
C5—C10—C11—C7
−0.35 (17)
134.3 (2)
−117.5 (2)
−44.16 (18)
64.06 (18)
−15.9 (3)
162.55 (16)
−149.1 (2)
29.38 (17)
118.2 (2)
−63.30 (18)
−0.9 (3)
131.62 (18)
−125.04 (17)
−133.26 (18)
−0.7 (2)
102.62 (16)
124.02 (18)
−103.44 (15)
−0.10 (12)
−0.07 (17)
−109.58 (14)
109.40 (14)
−0.10 (12)
−33.26 (17)
73.97 (16)
−129.09 (15)
−21.86 (17)
122.67 (18)
−107.91 (14)
0.10 (12)
−133.34 (17)
−3.91 (17)
104.10 (14)

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supplementary materials
sup-7
Hydrogen-bond geometry (Å, °)
D—H···A
C2—H2···O2i
C3—H3···O2ii
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+3/2, −z+1.
D—HH···AD···AD—H···A
1.002.583.303 (2)129
1.002.593.335 (2)131

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supplementary materials
sup-8
Fig. 1

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supplementary materials
sup-9
Fig. 2

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supplementary materials
sup-10
Fig. 3