6-[(2E)-3,7-Dimethyl-octa-2,6-dien-1-yl]-5,7-dihy-droxy-8-(2-methyl-butano-yl)-4-phenyl-2H-chromen-2-one-6-[(2E)-3,7-dimethyl-octa-2,6-dien-1-yl]-5,7-dihy-droxy-8-(3-methyl-butano-yl)-4-phenyl-2H-chromen-2-one (1/1) from Mesua elegans.

Abstract

The title co-crystal, C(30)H(34)O(5)·C(30)H(34)O(5), comprises a 1:1 mixture of two mostly superimposed mol-ecules with the same chemical formula that differ in the nature of the substituent (2-methyl-butanoyl or 3-methyl-butano-yl) bound at the exocyclic ketone. The lactone ring is close to planar (r.m.s. deviation = 0.058 Å) and the phenyl ring is twisted out of this plane [dihedral angle = 60.08 (9)°]. The geranyl substituent is almost normal to benzene ring to which it is connected [C-C-C(ar)-C(ar) (ar = aromatic) torsion angle = -87.8 (2)°]. Intra-molecular O-H⋯O and O-H⋯π inter-actions are formed. In the crystal, supra-molecular chains are formed along the a axis owing to C-H⋯O contacts, with the lactone carbonyl atom accepting two such bonds.

Full text

Page 1

6-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-
5,7-dihydroxy-8-(2-methylbutanoyl)-4-
phenyl-2H-chromen-2-one–6-[(2E)-3,7-
dimethylocta-2,6-dien-1-yl]-5,7-
dihydroxy-8-(3-methylbutanoyl)-4-
phenyl-2H-chromen-2-one (1/1) from
Mesua elegans1
Gomathi Chan,aKhalijah Awang,aNor Hadiani Ismail,b
Seik Weng Nga,cand Edward R. T. Tiekinka*
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia,
bFaculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam,
Malaysia, andcChemistry Department, Faculty of, Science, King Abdulaziz
University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com
Received 23 February 2012; accepted 27 February 2012
Key indicators: single-crystal X-ray study; T = 100 K; mean ?(C–C) = 0.003 A ˚;
disorder in main residue; R factor = 0.066; wR factor = 0.208; data-to-parameter
ratio = 14.7.
The title co-crystal, C30H34O5?C30H34O5, comprises a 1:1
mixture of two mostly superimposed molecules with the same
chemical formula that differ in the nature of the substituent
(2-methylbutanoylor3-methylbutanoyl)
exocyclic ketone. The lactone ring is close to planar (r.m.s.
deviation = 0.058 A˚) and the phenyl ring is twisted out of this
plane [dihedral angle = 60.08 (9)?]. The geranyl substituent is
almost normal to benzene ring to which it is connected [C—
C—Car—Car (ar = aromatic) torsion angle = ?87.8 (2)?].
Intramolecular O—H???O and O—H???? interactions are
formed. In the crystal, supramolecular chains are formed
along the a axis owing to C—H???O contacts, with the lactone
carbonyl atom accepting two such bonds.
boundat the
Related literature
For the spectroscopic characterization of the title material,
see: Verotta et al. (2004) and for its acetylcholinesterase
(AChE) inhibitory properties, see: Awang et al. (2010).
Experimental
Crystal data
C30H34O5?C30H34O5
Mr= 949.14
Triclinic, P1
a = 5.9426 (2) A˚
b = 13.4688 (5) A˚
c = 16.3275 (6) A˚
? = 91.955 (3)?
? = 99.515 (3)?
? = 95.834 (3)?
V = 1280.47 (8) A˚3
Z = 1
Cu K? radiation
? = 0.66 mm?1
T = 100 K
0.30 ? 0.15 ? 0.05 mm
Data collection
Agilent SuperNova Dual
diffractometer with an Atlas
detector
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
Tmin= 0.826, Tmax= 0.968
25960 measured reflections
5330 independent reflections
4528 reflections with I > 2?(I)
Rint= 0.045
Refinement
R[F2> 2?(F2)] = 0.066
wR(F2) = 0.208
S = 1.01
5330 reflections
363 parameters
54 restraints
H atoms treated by a mixture of
independent and constrained
refinement
??max= 0.57 e A˚?3
??min= ?0.53 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
Cg1 is the centroid of the C10–C15 ring.
D—H???A
O4—H4o???O5
O4—H4o???O50
O3—H3o???Cg1
C2—H2???O2i
C15—H15???O2ii
Symmetry codes: (i) ?x þ 3;?y þ 1;?z þ 1; (ii) ?x þ 2;?y þ 1;?z þ 1.
D—HH???AD???AD—H???A
0.85 (1)
0.85 (1)
0.84 (2)
0.95
0.95
1.54 (4)
1.76 (4)
2.56 (4)
2.47
2.59
2.35 (3)
2.55 (3)
3.355 (2)
3.408 (2)
3.351 (2)
158 (4)
154 (3)
158 (4)
169
137
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement:
CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to
solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to
refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics:
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006);
software used to prepare material for publication: publCIF (Westrip,
2010).
The authors thank the Ministry of Higher Education
(Malaysia) for funding structural studies through the High-
ImpactResearch scheme
Ministry of Science and Technology grant (02–01-01-SF0329)
and University of Malaya student’s grant (PPP 369/2010B) for
the isolation and elucidation of the co-crystal.
(UM.C/HIR/MOHE/SC/12),
organic compounds
Acta Cryst. (2012). E68, o939–o940 doi:10.1107/S1600536812008628Chan et al.
o939
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
1Additional correspondence author, e-mail: khalijah@um.edu.my.

Page 2

Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: HB6652).
References
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Awang, K., Chan, G., Litaudon, M., Ismail, N. H., Martin, M.-T. & Gueritte, F.
(2010). Bioorg. Med. Chem. 18, 7873–7877.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Verotta, L., Lovaglio, E., Vidari, G., Finzi, P. V., Neri, M. G., Raimondi, A.,
Parapini, S., Taramelli, D., Riva, A. & Bombardelli, E. (2004). Phytochem-
istry, 65, 2867–2879.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
organic compounds
o940
Chan et al.
? C30H34O5?C30H34O5
Acta Cryst. (2012). E68, o939–o940

Page 3

supplementary materials
sup-1
Acta Cryst. (2012). E68, o939–o940
supplementary materials
Acta Cryst. (2012). E68, o939–o940 [doi:10.1107/S1600536812008628]
6-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-8-(2-methylbutanoyl)-4-
phenyl-2H-chromen-2-one–6-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-di-
hydroxy-8-(3-methylbutanoyl)-4-phenyl-2H-chromen-2-one (1/1) from Mesua
elegans
Gomathi Chan, Khalijah Awang, Nor Hadiani Ismail, Seik Weng Ng and Edward R. T. Tiekink
Comment
The structure of the title co-crystal (I), previously isolated from Mesua ferrea, was elucidated by spectroscopic
measurements (Verotta et al., 2004). Both components possess the 4-phenylcoumarin skeleton, which is substituted by
two hydroxyl group at C-5 and C-7, and a geranyl group at C-6. The difference between the two compounds is the
substituent at position C-8; the first is substituted with 2-methylbutanoyl and the second is substituted with the 3-methyl-
butanoyl group. The title co-crystal have been evaluated as multi-drug resistant anti-bacterials (Verotta et al., 2004) and
for their acetylcholinesterase (AChE) inhibitory properties (Awang et al., 2010). Herein, a crystallographic analysis is
described.
The molecular components of the co-crystal (I) are shown in Figs 1 and 2. The r.m.s. deviation for the fitted atoms of
the lactone ring = 0.058 Å with maximum deviations of 0.043 (2) Å for the C3 atoms and -0.058 (2) Å for the C4 atom.
The phenyl ring is twisted out of this plane, forming a dihedral angle of 60.08 (9)°. The excocyclic carbonyl atom is co-
planar with the benzene ring to which it is connected with the C7—C8—C26—O5 torsion angle being 2.2 (10)°; the
equivalent torsion angle for the molecule with the 3-methylbutanoyl is 9.9 (9)°. The co-planarity is readily accounted for
in terms of intramolecular O—H···O hydrogen bonds. The geranyl group projects almost normal to the plane through the
benzene ring with the C5—C6—C16—C17 torsion angle being -87.8 (2)°. The second hydroxyl group forms an
intramolecular O—H···π interaction with the phenyl ring, Table 1.
In the crystal, the lactone-carbonyl atom participates in two C—H···O interactions, Table 1, to link molecules into a
supramolecular chain along the a axis, Fig. 3.
Experimental
Dried ground bark (1.5 kg) of Mesua elegans (Clusiaceae), collected from Sungai Badak Forest Reserve, Sintok, Kedah,
Malaysia, was extracted with hexane (3 × 4 L, 48 h) at room temperature. The hexane was evaporated to give a yellow
gum (120 g). A portion of the extract (10 g) was subjected to column chromatography over silica gel (230–400 mesh) and
eluted with hexane:ethyl acetate (from 9.5 to 0) and ethyl acetate:methanol (5:5) to give six fractions. The first fraction
was subjected to further silica gel chromatography and eluted with hexane:ethyl acetate (from 9.7 to 9.4) to produce two
other sub-fractions. The co-crystal was obtained from the second sub-fraction and recrystallized from its methanol
solution as colourless prisms.

Page 4

supplementary materials
sup-2
Acta Cryst. (2012). E68, o939–o940
Refinement
Carbon-bound H-atoms were placed in calculated positions [C—H = 0.95 to 1.00 Å, Uiso(H) = 1.2 to 1.5Ueq(C)] and were
included in the refinement in the riding model approximation. The hydroxy H-atoms were located in a difference Fourier
map, and were refined with a distance restraint of O—H = 0.84±0.01 Å; their Uiso values were refined.
The crystal is a co-crystal of two molecules having an identical chemical composition. One has an 2-methylbutanoyl
substituent in the fused-ring whereas the other has the isomeric 3-methylbutanoyl substituent. As the occupancy refined
to a nearly 1:1 ratio, the occupancy of each substituent was set as exactly 0.5.
The pairs of Cbenzene–Cketone, Cketone–Cmethine/methylene and C—O distances were restrained to within 0.01 Å of each other, and
the anisotropic displacement parameters of the primed atoms were set to those of the unprimed ones. The four-atom unit
was restrained to be nearly planar. For the atoms comprising the butyl fragment, 1,2-related C–C distances were
restrained to 1.540±0.005 and 1,3-related ones to 2.51±0.01 Å, and the anisotropic displacement parameters were
restrained to be nearly isotropic.
Computing details
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis
PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine
structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg,
2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Page 5

supplementary materials
sup-3
Acta Cryst. (2012). E68, o939–o940
Figure 1
The molecular structure of the first (2-methyl butanoyl) component of (I) showing displacement ellipsoids at the 50%
probability level.

Page 6

supplementary materials
sup-4
Acta Cryst. (2012). E68, o939–o940
Figure 2
The molecular structure of the second (3-methyl butanoyl) component of (I) showing displacement ellipsoids at the 50%
probability level.
Figure 3
A view in projection down the a axis of the unit-cell contents of (I). The C—H···O interactions are shown as orange
dashed lines.

Page 7

supplementary materials
sup-5
Acta Cryst. (2012). E68, o939–o940
6-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-8-(2- methylbutanoyl)-4-phenyl-2H-chromen-2-one–
6-[(2E)-3,7- dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-8-(3-methylbutanoyl)-4-phenyl- 2H-chromen-2-one (1/1)
Crystal data
C30H34O5·C30H34O5
Mr = 949.14
Triclinic, P1
Hall symbol: -P 1
a = 5.9426 (2) Å
b = 13.4688 (5) Å
c = 16.3275 (6) Å
α = 91.955 (3)°
β = 99.515 (3)°
γ = 95.834 (3)°
V = 1280.47 (8) Å3
Z = 1
F(000) = 508
Dx = 1.231 Mg m−3
Cu Kα radiation, λ = 1.54184 Å
Cell parameters from 8956 reflections
θ = 2.8–76.3°
µ = 0.66 mm−1
T = 100 K
Prism, colourless
0.30 × 0.15 × 0.05 mm
Data collection
Agilent SuperNova Dual
diffractometer with an Atlas detector
Radiation source: SuperNova (Cu) X-ray
Source
Mirror monochromator
Detector resolution: 10.4041 pixels mm-1
ω scan
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
Tmin = 0.826, Tmax = 0.968
25960 measured reflections
5330 independent reflections
4528 reflections with I > 2σ(I)
Rint = 0.045
θmax = 76.5°, θmin = 2.8°
h = −7→7
k = −16→16
l = −20→20
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.066
wR(F2) = 0.208
S = 1.01
5330 reflections
363 parameters
54 restraints
Primary atom site location: structure-invariant
direct methods
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
H atoms treated by a mixture of independent
and constrained refinement
w = 1/[σ2(Fo2) + (0.1357P)2 + 0.5208P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.57 e Å−3
Δρmin = −0.53 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
xyzUiso*/Ueq
Occ. (<1)
O1
O2
O3
H3o
O4
H4o
O5
O5′
C1
C2
0.9303 (2)
1.2727 (2)
0.7244 (2)
0.851 (3)
0.1977 (2)
0.198 (6)
0.284 (4)
0.308 (4)
1.1476 (3)
1.1949 (3)
0.47777 (9)
0.55978 (10)
0.13093 (9)
0.138 (2)
0.30693 (11)
0.3641 (14)
0.473 (2)
0.489 (2)
0.48355 (13)
0.40121 (13)
0.36863 (8)
0.41312 (9)
0.41205 (9)
0.4450 (14)
0.25255 (9)
0.232 (2)
0.218 (3)
0.223 (3)
0.41647 (12)
0.46801 (11)
0.0331 (3)
0.0390 (3)
0.0399 (4)
0.052 (7)*
0.0415 (4)
0.080 (10)*
0.046 (2)
0.046 (2)
0.0329 (4)
0.0325 (4)
0.50
0.50

Page 8

supplementary materials
sup-6
Acta Cryst. (2012). E68, o939–o940
H2
C3
C4
C5
C6
C7
C8
C9
C10
C11
H11
C12
H12
C13
H13
C14
H14
C15
H15
C16
H16A
H16B
C17
H17
C18
C19
H19A
H19B
H19C
C20
H20A
H20B
C21
H21A
H21B
C22
H22
C23
C24
H24A
H24B
H24C
C25
H25A
H25B
H25C
C26
C27
H27
1.3363
1.0417 (3)
0.8304 (3)
0.6749 (3)
0.4647 (3)
0.4069 (3)
0.5641 (3)
0.7747 (3)
1.0886 (3)
1.2800 (4)
1.3861
1.3170 (4)
1.4461
1.1665 (4)
1.1912
0.9803 (4)
0.8794
0.9392 (4)
0.8098
0.3045 (3)
0.3228
0.1435
0.3576 (3)
0.5157
0.2122 (3)
−0.0431 (3)
−0.0823
−0.1095
−0.1049
0.2995 (3)
0.4624
0.2117
0.2809 (5)
0.3737
0.1191
0.3627 (5)
0.5179
0.2449 (4)
0.3472 (5)
0.5074
0.2603
0.3409
0.0024 (6)
−0.0533
−0.0096
−0.0907
0.480 (2)
0.6207 (16)
0.7212
0.4046
0.31880 (13)
0.30996 (13)
0.22155 (13)
0.22110 (13)
0.31019 (14)
0.39885 (14)
0.39437 (13)
0.24091 (13)
0.18927 (16)
0.2055
0.11372 (18)
0.0774
0.09147 (16)
0.0395
0.14473 (15)
0.1305
0.21920 (14)
0.2552
0.12556 (14)
0.0817
0.1414
0.07200 (14)
0.0679
0.03001 (13)
0.02650 (17)
0.0682
−0.0426
0.0516
−0.01785 (14)
0.0082
0.0022
−0.13182 (16)
−0.1526
−0.1584
−0.17516 (16)
−0.1552
−0.23810 (17)
−0.27142 (19)
−0.2421
−0.2494
−0.3445
−0.2785 (4)
−0.2536
−0.3517
−0.2570
0.4832 (7)
0.5821 (7)
0.5942
0.5055
0.46420 (11)
0.40438 (11)
0.38407 (11)
0.33394 (11)
0.29808 (11)
0.30749 (11)
0.36031 (11)
0.52593 (11)
0.52804 (13)
0.4917
0.58338 (15)
0.5836
0.63781 (14)
0.6751
0.63803 (13)
0.6766
0.58222 (13)
0.5824
0.31303 (12)
0.3606
0.3026
0.23678 (13)
0.2355
0.17137 (12)
0.16256 (13)
0.2074
0.1658
0.1087
0.09938 (12)
0.1015
0.0468
0.09853 (15)
0.1499
0.0979
0.02434 (15)
0.0197
−0.03575 (14)
−0.10876 (16)
−0.1023
−0.1600
−0.1116
−0.0393 (2)
0.0100
−0.0407
−0.0895
0.2594 (10)
0.2569 (5)
0.3125
0.039*
0.0311 (4)
0.0308 (4)
0.0326 (4)
0.0340 (4)
0.0344 (4)
0.0344 (4)
0.0314 (4)
0.0330 (4)
0.0422 (5)
0.051*
0.0508 (6)
0.061*
0.0475 (5)
0.057*
0.0439 (5)
0.053*
0.0390 (4)
0.047*
0.0372 (4)
0.045*
0.045*
0.0377 (4)
0.045*
0.0336 (4)
0.0427 (5)
0.064*
0.064*
0.064*
0.0378 (4)
0.045*
0.045*
0.0547 (6)
0.066*
0.066*
0.0501 (5)
0.060*
0.0501 (5)
0.0590 (6)
0.089*
0.089*
0.089*
0.0989 (14)
0.148*
0.148*
0.148*
0.0424 (9)
0.0590 (13)
0.071*
0.50
0.50
0.50

Page 9

supplementary materials
sup-7
Acta Cryst. (2012). E68, o939–o940
C26′
C27′
H27A
H27B
C28
H28A
H28B
C29
H29A
H29B
H29C
C30
H30A
H30B
H30C
C28′
H28′
C29′
H29D
H29E
H29F
C30′
H30D
H30E
H30F
0.506 (2)
0.6741 (18)
0.8304
0.6755
0.7818 (6)
0.8578
0.6900
0.9641 (7)
1.0600
1.0598
0.8902
0.4816 (13)
0.3892
0.3803
0.5868
0.6076 (11)
0.4480
0.7783 (13)
0.7365
0.9333
0.7744
0.6254 (7)
0.5155
0.7814
0.5910
0.4880 (7)
0.5785 (8)
0.5578
0.6263
0.5736 (2)
0.5118
0.5676
0.6620 (3)
0.6530
0.6668
0.7235
0.6723 (6)
0.6764
0.6642
0.7336
0.6297 (4)
0.6489
0.7238 (4)
0.7635
0.7046
0.7635
0.5651 (3)
0.5051
0.5457
0.6025
0.2608 (9)
0.2554 (6)
0.2586
0.3029
0.1937 (2)
0.2025
0.1370
0.1995 (3)
0.1570
0.2547
0.1905
0.2447 (5)
0.2889
0.1905
0.2469
0.1732 (3)
0.1690
0.1787 (4)
0.1304
0.1794
0.2298
0.0980 (2)
0.0944
0.1029
0.0479
0.0424 (9)
0.0590 (13)
0.071*
0.071*
0.0311 (7)
0.037*
0.037*
0.0458 (9)
0.069*
0.069*
0.069*
0.117 (3)
0.176*
0.176*
0.176*
0.0737 (16)
0.088*
0.089 (2)
0.133*
0.133*
0.133*
0.0362 (8)
0.054*
0.054*
0.054*
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
0.50
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
O1
O2
O3
O4
O5
O5′
C1
C2
C3
C4
C5
C6
C7
C8
C9
C10
C11
C12
C13
C14
0.0368 (7)
0.0393 (7)
0.0433 (8)
0.0383 (7)
0.049 (4)
0.049 (4)
0.0351 (9)
0.0335 (9)
0.0353 (9)
0.0338 (9)
0.0381 (9)
0.0366 (9)
0.0364 (9)
0.0406 (10)
0.0355 (9)
0.0386 (9)
0.0449 (11)
0.0566 (13)
0.0650 (14)
0.0588 (13)
0.0244 (6)
0.0253 (6)
0.0231 (6)
0.0393 (8)
0.029 (7)
0.029 (7)
0.0258 (8)
0.0274 (9)
0.0255 (8)
0.0259 (8)
0.0248 (8)
0.0285 (9)
0.0337 (9)
0.0302 (9)
0.0263 (8)
0.0248 (8)
0.0420 (11)
0.0470 (12)
0.0336 (10)
0.0320 (10)
0.0359 (7)
0.0494 (8)
0.0500 (8)
0.0431 (8)
0.051 (4)
0.051 (4)
0.0366 (9)
0.0351 (9)
0.0329 (9)
0.0323 (8)
0.0351 (9)
0.0359 (9)
0.0317 (9)
0.0306 (8)
0.0315 (8)
0.0338 (9)
0.0431 (11)
0.0535 (13)
0.0455 (11)
0.0441 (11)
−0.0024 (5)
−0.0036 (5)
−0.0009 (5)
−0.0025 (6)
−0.010 (4)
−0.010 (4)
−0.0003 (7)
−0.0004 (7)
0.0016 (7)
−0.0013 (7)
0.0001 (7)
−0.0041 (7)
−0.0013 (7)
−0.0019 (7)
−0.0027 (7)
−0.0015 (7)
0.0092 (9)
0.0172 (10)
0.0064 (9)
0.0018 (9)
0.0040 (5)
0.0038 (6)
0.0025 (6)
0.0004 (6)
−0.012 (3)
−0.012 (3)
0.0062 (7)
0.0045 (7)
0.0089 (7)
0.0084 (7)
0.0098 (7)
0.0089 (7)
0.0061 (7)
0.0056 (7)
0.0083 (7)
0.0052 (7)
0.0131 (9)
0.0144 (10)
0.0128 (10)
0.0198 (9)
−0.0023 (5)
−0.0011 (5)
−0.0037 (5)
−0.0012 (6)
0.001 (6)
0.001 (6)
−0.0049 (7)
−0.0024 (7)
−0.0044 (6)
−0.0039 (6)
−0.0042 (7)
−0.0066 (7)
−0.0055 (7)
−0.0032 (7)
−0.0054 (6)
−0.0029 (7)
0.0075 (8)
0.0115 (10)
0.0069 (8)
0.0035 (8)

Page 10

supplementary materials
sup-8
Acta Cryst. (2012). E68, o939–o940
C15
C16
C17
C18
C19
C20
C21
C22
C23
C24
C25
C26
C27
C26′
C27′
C28
C29
C30
C28′
C29′
C30′
0.0453 (11)
0.0371 (9)
0.0322 (9)
0.0356 (9)
0.0368 (10)
0.0386 (10)
0.0848 (18)
0.0640 (14)
0.0633 (14)
0.0779 (17)
0.084 (2)
0.048 (3)
0.051 (4)
0.048 (3)
0.051 (4)
0.0366 (17)
0.050 (2)
0.115 (6)
0.078 (4)
0.101 (5)
0.051 (2)
0.0293 (9)
0.0306 (9)
0.0322 (9)
0.0264 (8)
0.0494 (12)
0.0322 (9)
0.0338 (11)
0.0358 (11)
0.0430 (11)
0.0476 (13)
0.146 (4)
0.0361 (12)
0.0474 (15)
0.0361 (12)
0.0474 (15)
0.0258 (16)
0.0336 (19)
0.101 (5)
0.064 (3)
0.068 (4)
0.0264 (16)
0.0441 (10)
0.0415 (10)
0.0470 (11)
0.0379 (9)
0.0400 (10)
0.0409 (10)
0.0472 (12)
0.0521 (13)
0.0439 (11)
0.0526 (13)
0.0572 (17)
0.0364 (11)
0.0629 (16)
0.0364 (11)
0.0629 (16)
0.0301 (16)
0.054 (2)
0.114 (6)
0.073 (4)
0.089 (4)
0.0316 (17)
0.0029 (8)
−0.0047 (7)
0.0008 (7)
−0.0008 (7)
−0.0012 (8)
−0.0008 (7)
0.0082 (11)
0.0076 (10)
0.0074 (10)
0.0122 (12)
−0.037 (2)
−0.0067 (14)
−0.020 (2)
−0.0067 (14)
−0.020 (2)
0.0024 (13)
−0.0012 (17)
−0.012 (5)
−0.001 (3)
−0.005 (3)
−0.0002 (15)
0.0137 (8)
0.0067 (8)
0.0055 (8)
0.0060 (7)
0.0056 (8)
0.0064 (8)
0.0157 (12)
0.0146 (11)
0.0083 (10)
0.0136 (12)
0.0231 (16)
−0.0059 (15)
−0.0257 (19)
−0.0059 (15)
−0.0257 (19)
0.0019 (13)
0.0135 (19)
−0.033 (5)
−0.001 (3)
−0.004 (4)
0.0093 (15)
−0.0001 (7)
−0.0072 (7)
−0.0077 (8)
−0.0002 (7)
−0.0044 (8)
−0.0050 (7)
−0.0017 (9)
−0.0051 (9)
−0.0009 (9)
−0.0113 (10)
−0.030 (2)
0.0013 (10)
0.0194 (12)
0.0013 (10)
0.0194 (12)
0.0110 (12)
0.0053 (17)
0.032 (5)
0.005 (3)
0.017 (3)
0.0057 (13)
Geometric parameters (Å, º)
O1—C9
O1—C1
O2—C1
O3—C5
O3—H3o
O4—C7
O4—H4o
O5—C26
O5′—C26′
C1—C2
C2—C3
C2—H2
C3—C4
C3—C10
C4—C9
C4—C5
C5—C6
C6—C7
C6—C16
C7—C8
C8—C9
C8—C26
C8—C26′
C10—C11
C10—C15
C11—C12
1.368 (2)
1.388 (2)
1.213 (2)
1.361 (2)
0.844 (10)
1.335 (2)
0.853 (10)
1.240 (6)
1.238 (6)
1.437 (3)
1.355 (2)
0.9500
1.450 (3)
1.494 (2)
1.405 (3)
1.425 (2)
1.375 (3)
1.402 (3)
1.514 (2)
1.427 (3)
1.405 (3)
1.483 (6)
1.484 (6)
1.389 (3)
1.398 (3)
1.394 (3)
C19—H19C
C20—C21
C20—H20A
C20—H20B
C21—C22
C21—H21A
C21—H21B
C22—C23
C22—H22
C23—C25
C23—C24
C24—H24A
C24—H24B
C24—H24C
C25—H25A
C25—H25B
C25—H25C
C26—C27
C27—C28
C27—C30
C27—H27
C26′—C27′
C27′—C28′
C27′—H27A
C27′—H27B
C28—C29
0.9800
1.527 (3)
0.9900
0.9900
1.499 (3)
0.9900
0.9900
1.329 (3)
0.9500
1.479 (4)
1.500 (3)
0.9800
0.9800
0.9800
0.9800
0.9800
0.9800
1.504 (6)
1.528 (4)
1.538 (5)
1.0000
1.510 (6)
1.541 (11)
0.9900
0.9900
1.516 (4)

Page 11

supplementary materials
sup-9
Acta Cryst. (2012). E68, o939–o940
C11—H11
C12—C13
C12—H12
C13—C14
C13—H13
C14—C15
C14—H14
C15—H15
C16—C17
C16—H16A
C16—H16B
C17—C18
C17—H17
C18—C19
C18—C20
C19—H19A
C19—H19B
0.9500
1.380 (3)
0.9500
1.379 (3)
0.9500
1.391 (3)
0.9500
0.9500
1.511 (3)
0.9900
0.9900
1.327 (3)
0.9500
1.496 (3)
1.511 (3)
0.9800
0.9800
C28—H28A
C28—H28B
C29—H29A
C29—H29B
C29—H29C
C30—H30A
C30—H30B
C30—H30C
C28′—C30′
C28′—C29′
C28′—H28′
C29′—H29D
C29′—H29E
C29′—H29F
C30′—H30D
C30′—H30E
C30′—H30F
0.9900
0.9900
0.9800
0.9800
0.9800
0.9800
0.9800
0.9800
1.505 (4)
1.531 (4)
1.0000
0.9800
0.9800
0.9800
0.9800
0.9800
0.9800
C9—O1—C1
C5—O3—H3o
C7—O4—H4o
O2—C1—O1
O2—C1—C2
O1—C1—C2
C3—C2—C1
C3—C2—H2
C1—C2—H2
C2—C3—C4
C2—C3—C10
C4—C3—C10
C9—C4—C5
C9—C4—C3
C5—C4—C3
O3—C5—C6
O3—C5—C4
C6—C5—C4
C5—C6—C7
C5—C6—C16
C7—C6—C16
O4—C7—C6
O4—C7—C8
C6—C7—C8
C9—C8—C7
C9—C8—C26
C7—C8—C26
C9—C8—C26′
C7—C8—C26′
O1—C9—C8
O1—C9—C4
123.73 (14)
108.8 (19)
103 (2)
116.26 (17)
127.17 (18)
116.46 (15)
121.27 (17)
119.4
119.4
120.15 (17)
118.72 (17)
121.03 (15)
116.29 (17)
118.02 (16)
125.66 (17)
114.94 (16)
122.49 (17)
122.57 (17)
118.48 (16)
121.17 (17)
120.24 (17)
116.21 (16)
121.54 (17)
122.22 (17)
116.14 (17)
129.2 (6)
114.7 (6)
123.4 (6)
120.5 (6)
117.12 (16)
119.40 (16)
C20—C21—H21A
C22—C21—H21B
C20—C21—H21B
H21A—C21—H21B
C23—C22—C21
C23—C22—H22
C21—C22—H22
C22—C23—C25
C22—C23—C24
C25—C23—C24
C23—C24—H24A
C23—C24—H24B
H24A—C24—H24B
C23—C24—H24C
H24A—C24—H24C
H24B—C24—H24C
C23—C25—H25A
C23—C25—H25B
H25A—C25—H25B
C23—C25—H25C
H25A—C25—H25C
H25B—C25—H25C
O5—C26—C8
O5—C26—C27
C8—C26—C27
C26—C27—C28
C26—C27—C30
C28—C27—C30
C26—C27—H27
C28—C27—H27
C30—C27—H27
109.3
109.3
109.3
108.0
128.0 (2)
116.0
116.0
124.1 (2)
122.0 (2)
113.8 (2)
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
119.2 (19)
116.9 (16)
123.9 (8)
109.4 (9)
115.0 (7)
113.0 (5)
106.2
106.2
106.2

Page 12

supplementary materials
sup-10
Acta Cryst. (2012). E68, o939–o940
C8—C9—C4
C11—C10—C15
C11—C10—C3
C15—C10—C3
C10—C11—C12
C10—C11—H11
C12—C11—H11
C13—C12—C11
C13—C12—H12
C11—C12—H12
C14—C13—C12
C14—C13—H13
C12—C13—H13
C13—C14—C15
C13—C14—H14
C15—C14—H14
C14—C15—C10
C14—C15—H15
C10—C15—H15
C17—C16—C6
C17—C16—H16A
C6—C16—H16A
C17—C16—H16B
C6—C16—H16B
H16A—C16—H16B
C18—C17—C16
C18—C17—H17
C16—C17—H17
C17—C18—C19
C17—C18—C20
C19—C18—C20
C18—C19—H19A
C18—C19—H19B
H19A—C19—H19B
C18—C19—H19C
H19A—C19—H19C
H19B—C19—H19C
C18—C20—C21
C18—C20—H20A
C21—C20—H20A
C18—C20—H20B
C21—C20—H20B
H20A—C20—H20B
C22—C21—C20
C22—C21—H21A
123.48 (16)
119.28 (18)
120.61 (17)
120.11 (17)
120.20 (19)
119.9
119.9
120.2 (2)
119.9
119.9
120.0 (2)
120.0
120.0
120.48 (19)
119.8
119.8
119.84 (19)
120.1
120.1
110.01 (16)
109.7
109.7
109.7
109.7
108.2
128.44 (18)
115.8
115.8
123.89 (18)
120.64 (18)
115.46 (16)
109.5
109.5
109.5
109.5
109.5
109.5
114.04 (17)
108.7
108.7
108.7
108.7
107.6
111.63 (19)
109.3
O5′—C26′—C8
O5′—C26′—C27′
C8—C26′—C27′
C26′—C27′—C28′
C26′—C27′—H27A
C28′—C27′—H27A
C26′—C27′—H27B
C28′—C27′—H27B
H27A—C27′—H27B
C29—C28—C27
C29—C28—H28A
C27—C28—H28A
C29—C28—H28B
C27—C28—H28B
H28A—C28—H28B
C28—C29—H29A
C28—C29—H29B
H29A—C29—H29B
C28—C29—H29C
H29A—C29—H29C
H29B—C29—H29C
C27—C30—H30A
C27—C30—H30B
H30A—C30—H30B
C27—C30—H30C
H30A—C30—H30C
H30B—C30—H30C
C30′—C28′—C29′
C30′—C28′—C27′
C29′—C28′—C27′
C30′—C28′—H28′
C29′—C28′—H28′
C27′—C28′—H28′
C28′—C29′—H29D
C28′—C29′—H29E
H29D—C29′—H29E
C28′—C29′—H29F
H29D—C29′—H29F
H29E—C29′—H29F
C28′—C30′—H30D
C28′—C30′—H30E
H30D—C30′—H30E
C28′—C30′—H30F
H30D—C30′—H30F
H30E—C30′—H30F
118.4 (19)
117.3 (17)
124.3 (9)
110.6 (7)
109.5
109.5
109.5
109.5
108.1
113.2 (5)
108.9
108.9
108.9
108.9
107.8
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5 (4)
112.7 (6)
105.2 (7)
109.8
109.8
109.8
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
C9—O1—C1—O2
C9—O1—C1—C2
O2—C1—C2—C3
174.82 (16)
−8.6 (2)
−178.28 (18)
C4—C3—C10—C15
C15—C10—C11—C12
C3—C10—C11—C12
−59.2 (2)
2.7 (3)
−177.2 (2)

Page 13

supplementary materials
sup-11
Acta Cryst. (2012). E68, o939–o940
O1—C1—C2—C3
C1—C2—C3—C4
C1—C2—C3—C10
C2—C3—C4—C9
C10—C3—C4—C9
C2—C3—C4—C5
C10—C3—C4—C5
C9—C4—C5—O3
C3—C4—C5—O3
C9—C4—C5—C6
C3—C4—C5—C6
O3—C5—C6—C7
C4—C5—C6—C7
O3—C5—C6—C16
C4—C5—C6—C16
C5—C6—C7—O4
C16—C6—C7—O4
C5—C6—C7—C8
C16—C6—C7—C8
O4—C7—C8—C9
C6—C7—C8—C9
O4—C7—C8—C26
C6—C7—C8—C26
O4—C7—C8—C26′
C6—C7—C8—C26′
C1—O1—C9—C8
C1—O1—C9—C4
C7—C8—C9—O1
C26—C8—C9—O1
C26′—C8—C9—O1
C7—C8—C9—C4
C26—C8—C9—C4
C26′—C8—C9—C4
C5—C4—C9—O1
C3—C4—C9—O1
C5—C4—C9—C8
C3—C4—C9—C8
C2—C3—C10—C11
C4—C3—C10—C11
C2—C3—C10—C15
5.6 (3)
3.2 (3)
−173.11 (16)
−9.5 (3)
166.80 (16)
168.59 (17)
−15.1 (3)
169.56 (16)
−8.5 (3)
−9.6 (3)
172.29 (17)
−175.86 (16)
3.4 (3)
0.2 (3)
179.46 (16)
−177.50 (16)
6.4 (3)
4.2 (3)
−171.91 (17)
176.91 (16)
−4.9 (3)
−3.1 (8)
175.1 (8)
−5.2 (8)
173.0 (8)
−177.96 (15)
2.4 (2)
178.44 (15)
−1.5 (9)
0.6 (9)
−2.0 (3)
178.1 (9)
−179.8 (8)
−171.55 (15)
6.7 (2)
8.9 (3)
−172.90 (16)
−63.0 (2)
120.7 (2)
117.1 (2)
C10—C11—C12—C13
C11—C12—C13—C14
C12—C13—C14—C15
C13—C14—C15—C10
C11—C10—C15—C14
C3—C10—C15—C14
C5—C6—C16—C17
C7—C6—C16—C17
C6—C16—C17—C18
C16—C17—C18—C19
C16—C17—C18—C20
C17—C18—C20—C21
C19—C18—C20—C21
C18—C20—C21—C22
C20—C21—C22—C23
C21—C22—C23—C25
C21—C22—C23—C24
C9—C8—C26—O5
C7—C8—C26—O5
C26′—C8—C26—O5
C9—C8—C26—C27
C7—C8—C26—C27
C26′—C8—C26—C27
O5—C26—C27—C28
C8—C26—C27—C28
O5—C26—C27—C30
C8—C26—C27—C30
C9—C8—C26′—O5′
C7—C8—C26′—O5′
C26—C8—C26′—O5′
C9—C8—C26′—C27′
C7—C8—C26′—C27′
C26—C8—C26′—C27′
O5′—C26′—C27′—C28′
C8—C26′—C27′—C28′
C26—C27—C28—C29
C30—C27—C28—C29
C26′—C27′—C28′—C30′
C26′—C27′—C28′—C29′
−1.6 (4)
−0.6 (4)
1.7 (3)
−0.6 (3)
−1.6 (3)
178.26 (18)
−87.8 (2)
88.2 (2)
−135.2 (2)
−1.5 (3)
178.18 (18)
102.3 (2)
−78.0 (2)
178.11 (19)
−119.9 (3)
−0.6 (5)
177.0 (2)
−177.9 (19)
2.2 (10)
165 (12)
2.8 (19)
−177.2 (10)
−14 (12)
−97.7 (14)
81.7 (14)
30.8 (11)
−149.8 (11)
−172.3 (17)
9.9 (9)
−8 (14)
8.4 (18)
−169.4 (9)
173 (14)
−27.9 (12)
151.4 (12)
−167.9 (5)
62.5 (9)
−65.2 (9)
175.6 (8)
Hydrogen-bond geometry (Å, º)
Cg1 is the centroid of the C10–C15 ring.
D—H···AD—HH···AD···AD—H···A
O4—H4o···O5
O4—H4o···O5′
O3—H3o···Cg1
0.85 (1)
0.85 (1)
0.84 (2)
1.54 (4)
1.76 (4)
2.56 (4)
2.35 (3)
2.55 (3)
3.355 (2)
158 (4)
154 (3)
158 (4)

Page 14

supplementary materials
sup-12
Acta Cryst. (2012). E68, o939–o940
C2—H2···O2i
C15—H15···O2ii
0.95
0.95
2.47
2.59
3.408 (2)
3.351 (2)
169
137
Symmetry codes: (i) −x+3, −y+1, −z+1; (ii) −x+2, −y+1, −z+1.