(E)-3-[4-(Pent-yloxy)phen-yl]-1-phenyl-prop-2-en-1-one.

The title compound, C(20)H(22)O(2), crystallizes with two independent mol-ecules in the asymmetric unit. In each mol-ecule, all the non-H atoms lie in a common plane (r.m.s. deviations of 0.098 and 0.079 Å). There is a π-π stacking inter-action in the crystal structure. The central aromatic rings of the two mol-ecules, which are stacked head-to-tail one above the other, are separated by centroid-to-centroid distances of 3.872 (13) and 3.999 (10) Å.

Related literature

For background information on chalcones and their properties, see: Achanta et al. (2006 ▶); Zhang et al. (2009 ▶); Tran et al. (2009 ▶); Yagura et al. (2008 ▶); Sarissky et al. (2008 ▶); Tang et al. (2008 ▶); Srivastava et al. (2008 ▶); For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Rosli et al. (2006 ▶); Harrison et al. (2006 ▶). For the synthesis, see: Wattanasin & Murphy (1980 ▶).

Experimental

Crystal data

C20H22O2

M = 294.38

Monoclinic,

a = 7.4881 (4) Å

b = 21.3067 (11) Å

c = 20.8328 (11) Å

β = 93.974 (4)°

V = 3315.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 173 K

0.38 × 0.22 × 0.22 mm

Data collection

Stoe IPDS II two-circle-diffractometer

Absorption correction: none

25934 measured reflections

5819 independent reflections

3319 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.101

S = 0.82

5819 reflections

398 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.19 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016754/su2111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016754/su2111Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H22O2	F(000) = 1264
Mr = 294.38	Dx = 1.179 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10828 reflections
a = 7.4881 (4) Å	θ = 2.2–25.4°
b = 21.3067 (11) Å	µ = 0.07 mm−1
c = 20.8328 (11) Å	T = 173 K
β = 93.974 (4)°	Needle, light yellow
V = 3315.8 (3) Å3	0.38 × 0.22 × 0.22 mm
Z = 8

STOE IPDS II two-circle-diffractometer	3319 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.086
graphite	θmax = 25.0°, θmin = 2.2°
ω scans	h = −8→8
25934 measured reflections	k = −25→25
5819 independent reflections	l = −24→24

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0461P)2] where P = (Fo2 + 2Fc2)/3
S = 0.82	(Δ/σ)max < 0.001
5819 reflections	Δρmax = 0.15 e Å−3
398 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0076 (8)

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 matrix. 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, 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.

	x	y	z	Uiso*/Ueq
O1	0.3753 (2)	0.28357 (6)	0.50789 (6)	0.0563 (4)
O2	0.36921 (18)	0.62946 (6)	0.31330 (6)	0.0438 (3)
C1	0.4030 (2)	0.27970 (9)	0.45038 (8)	0.0374 (4)
C2	0.4045 (2)	0.33580 (9)	0.40938 (8)	0.0377 (4)
H2	0.4199	0.3314	0.3647	0.045*
C3	0.3843 (2)	0.39303 (9)	0.43424 (9)	0.0391 (4)
H3	0.3695	0.3943	0.4791	0.047*
C4	0.3530 (3)	0.68540 (8)	0.35105 (8)	0.0404 (5)
H4A	0.4567	0.6891	0.3830	0.049*
H4B	0.2425	0.6836	0.3745	0.049*
C5	0.3465 (3)	0.74114 (9)	0.30660 (8)	0.0410 (5)
H5A	0.2375	0.7387	0.2769	0.049*
H5B	0.4519	0.7403	0.2804	0.049*
C6	0.3451 (3)	0.80230 (9)	0.34415 (8)	0.0407 (5)
H6A	0.2424	0.8018	0.3716	0.049*
H6B	0.4558	0.8048	0.3729	0.049*
C7	0.3323 (3)	0.86063 (9)	0.30226 (9)	0.0485 (5)
H7A	0.4293	0.8596	0.2723	0.058*
H7B	0.2168	0.8600	0.2761	0.058*
C8	0.3457 (3)	0.92128 (10)	0.34037 (12)	0.0625 (6)
H8A	0.3372	0.9570	0.3107	0.094*
H8B	0.4608	0.9227	0.3658	0.094*
H8C	0.2480	0.9233	0.3692	0.094*
C11	0.4342 (2)	0.21639 (9)	0.42220 (8)	0.0344 (4)
C12	0.4295 (2)	0.20512 (9)	0.35622 (8)	0.0400 (4)
H12	0.4078	0.2388	0.3269	0.048*
C13	0.4562 (3)	0.14507 (9)	0.33307 (9)	0.0481 (5)
H13	0.4541	0.1379	0.2880	0.058*
C14	0.4859 (3)	0.09584 (10)	0.37528 (10)	0.0527 (5)
H14	0.5021	0.0546	0.3593	0.063*
C15	0.4920 (3)	0.10636 (10)	0.44094 (10)	0.0544 (6)
H15	0.5140	0.0725	0.4701	0.065*
C16	0.4661 (3)	0.16618 (9)	0.46385 (9)	0.0463 (5)
H16	0.4701	0.1731	0.5090	0.056*
C21	0.3818 (2)	0.45381 (9)	0.40194 (8)	0.0366 (4)
C22	0.4064 (2)	0.46178 (9)	0.33614 (8)	0.0419 (5)
H22	0.4264	0.4261	0.3103	0.050*
C23	0.4021 (3)	0.52028 (9)	0.30860 (9)	0.0438 (5)
H23	0.4190	0.5246	0.2640	0.053*
C24	0.3730 (2)	0.57350 (9)	0.34540 (8)	0.0373 (4)
C25	0.3491 (3)	0.56698 (9)	0.41056 (8)	0.0422 (5)
H25	0.3308	0.6029	0.4363	0.051*
C26	0.3522 (3)	0.50777 (9)	0.43742 (9)	0.0431 (5)
H26	0.3334	0.5036	0.4818	0.052*
O1A	0.8034 (2)	0.81245 (6)	0.24815 (6)	0.0549 (4)
O2A	0.90510 (18)	0.45190 (6)	0.41506 (5)	0.0432 (3)
C1A	0.8272 (2)	0.80873 (9)	0.30728 (8)	0.0386 (4)
C2A	0.8414 (2)	0.74769 (9)	0.33972 (8)	0.0383 (4)
H2A	0.8414	0.7464	0.3853	0.046*
C3A	0.8545 (2)	0.69393 (9)	0.30771 (8)	0.0386 (4)
H3A	0.8536	0.6969	0.2622	0.046*
C4A	0.9039 (3)	0.39658 (8)	0.37602 (8)	0.0407 (4)
H4A1	1.0081	0.3967	0.3493	0.049*
H4A2	0.7933	0.3951	0.3471	0.049*
C5A	0.9124 (3)	0.34046 (9)	0.42018 (9)	0.0422 (5)
H5A1	0.8057	0.3402	0.4457	0.051*
H5A2	1.0198	0.3438	0.4505	0.051*
C6A	0.9201 (3)	0.27920 (8)	0.38292 (9)	0.0448 (5)
H6A1	0.8104	0.2755	0.3538	0.054*
H6A2	1.0237	0.2806	0.3559	0.054*
C7A	0.9362 (3)	0.22144 (10)	0.42529 (11)	0.0575 (6)
H7A1	0.8292	0.2185	0.4505	0.069*
H7A2	1.0424	0.2259	0.4560	0.069*
C8A	0.9535 (3)	0.16114 (10)	0.38681 (14)	0.0798 (8)
H8A1	0.9630	0.1253	0.4163	0.120*
H8A2	1.0609	0.1633	0.3626	0.120*
H8A3	0.8477	0.1561	0.3568	0.120*
C11A	0.8432 (2)	0.86778 (9)	0.34646 (8)	0.0364 (4)
C12A	0.8455 (3)	0.86841 (9)	0.41317 (8)	0.0441 (5)
H12A	0.8404	0.8300	0.4361	0.053*
C13A	0.8553 (3)	0.92462 (10)	0.44644 (10)	0.0533 (5)
H13A	0.8548	0.9246	0.4920	0.064*
C14A	0.8656 (3)	0.98053 (10)	0.41389 (10)	0.0525 (5)
H14A	0.8725	1.0190	0.4370	0.063*
C15A	0.8661 (3)	0.98060 (9)	0.34781 (10)	0.0512 (5)
H15A	0.8751	1.0192	0.3254	0.061*
C16A	0.8533 (3)	0.92468 (9)	0.31398 (9)	0.0437 (5)
H16A	0.8514	0.9251	0.2683	0.052*
C21A	0.8699 (2)	0.63097 (9)	0.33500 (8)	0.0367 (4)
C22A	0.8770 (3)	0.62003 (9)	0.40134 (8)	0.0412 (5)
H22A	0.8715	0.6546	0.4299	0.049*
C23A	0.8918 (3)	0.56028 (9)	0.42609 (9)	0.0431 (5)
H23A	0.8994	0.5542	0.4714	0.052*
C24A	0.8957 (2)	0.50891 (8)	0.38534 (8)	0.0361 (4)
C25A	0.8902 (2)	0.51804 (9)	0.31898 (8)	0.0405 (5)
H25A	0.8943	0.4833	0.2906	0.049*
C26A	0.8787 (3)	0.57867 (9)	0.29517 (8)	0.0420 (5)
H26A	0.8766	0.5849	0.2500	0.050*

	U11	U22	U33	U12	U13	U23
O1	0.0865 (11)	0.0481 (9)	0.0348 (7)	0.0088 (8)	0.0074 (7)	−0.0041 (6)
O2	0.0578 (8)	0.0340 (8)	0.0403 (7)	−0.0030 (6)	0.0070 (6)	−0.0019 (6)
C1	0.0362 (10)	0.0384 (11)	0.0372 (10)	0.0006 (8)	0.0002 (8)	−0.0023 (8)
C2	0.0400 (11)	0.0369 (11)	0.0365 (9)	0.0005 (9)	0.0039 (8)	−0.0026 (8)
C3	0.0373 (10)	0.0402 (12)	0.0398 (10)	−0.0013 (9)	0.0016 (8)	−0.0026 (8)
C4	0.0469 (11)	0.0327 (11)	0.0419 (10)	−0.0040 (9)	0.0052 (8)	−0.0031 (8)
C5	0.0434 (11)	0.0382 (11)	0.0415 (10)	−0.0026 (9)	0.0034 (8)	0.0014 (8)
C6	0.0416 (11)	0.0379 (11)	0.0428 (10)	−0.0014 (9)	0.0033 (8)	0.0011 (8)
C7	0.0478 (12)	0.0419 (12)	0.0556 (12)	−0.0010 (10)	0.0019 (9)	0.0054 (9)
C8	0.0582 (14)	0.0398 (13)	0.0881 (16)	0.0016 (11)	−0.0051 (12)	0.0027 (12)
C11	0.0310 (9)	0.0323 (10)	0.0401 (9)	0.0001 (8)	0.0037 (7)	−0.0001 (8)
C12	0.0456 (11)	0.0365 (11)	0.0380 (9)	0.0028 (9)	0.0036 (8)	−0.0008 (8)
C13	0.0592 (13)	0.0392 (12)	0.0470 (11)	0.0030 (10)	0.0114 (9)	−0.0082 (9)
C14	0.0604 (14)	0.0357 (12)	0.0638 (13)	0.0038 (10)	0.0168 (10)	−0.0028 (10)
C15	0.0715 (15)	0.0389 (12)	0.0540 (12)	0.0060 (11)	0.0131 (11)	0.0108 (10)
C16	0.0553 (12)	0.0422 (12)	0.0425 (10)	0.0025 (10)	0.0104 (9)	0.0017 (9)
C21	0.0343 (10)	0.0344 (11)	0.0409 (10)	−0.0019 (8)	0.0031 (8)	−0.0026 (8)
C22	0.0464 (11)	0.0390 (12)	0.0410 (10)	−0.0002 (9)	0.0079 (8)	−0.0077 (9)
C23	0.0549 (12)	0.0406 (12)	0.0369 (10)	−0.0022 (10)	0.0099 (9)	−0.0036 (9)
C24	0.0380 (10)	0.0343 (11)	0.0400 (10)	−0.0042 (8)	0.0046 (8)	0.0012 (8)
C25	0.0527 (12)	0.0341 (11)	0.0405 (10)	−0.0031 (9)	0.0080 (8)	−0.0071 (8)
C26	0.0545 (12)	0.0387 (12)	0.0368 (10)	−0.0040 (10)	0.0077 (9)	−0.0038 (8)
O1A	0.0860 (11)	0.0418 (8)	0.0360 (7)	0.0002 (8)	−0.0008 (7)	0.0018 (6)
O2A	0.0588 (9)	0.0313 (8)	0.0397 (7)	0.0033 (6)	0.0043 (6)	0.0012 (6)
C1A	0.0390 (11)	0.0364 (11)	0.0404 (10)	0.0007 (9)	0.0022 (8)	0.0015 (8)
C2A	0.0435 (11)	0.0351 (11)	0.0364 (9)	0.0001 (9)	0.0035 (8)	0.0001 (8)
C3A	0.0416 (11)	0.0381 (11)	0.0360 (9)	0.0008 (9)	0.0015 (8)	0.0020 (8)
C4A	0.0464 (11)	0.0333 (11)	0.0418 (10)	0.0007 (9)	−0.0011 (8)	−0.0022 (8)
C5A	0.0406 (11)	0.0402 (12)	0.0460 (11)	−0.0001 (9)	0.0042 (8)	0.0038 (9)
C6A	0.0455 (11)	0.0323 (11)	0.0557 (11)	−0.0029 (9)	−0.0018 (9)	0.0051 (9)
C7A	0.0435 (12)	0.0408 (13)	0.0879 (15)	−0.0026 (10)	0.0012 (11)	0.0214 (11)
C8A	0.0639 (16)	0.0321 (13)	0.140 (2)	−0.0054 (12)	−0.0151 (15)	0.0103 (14)
C11A	0.0342 (10)	0.0334 (11)	0.0416 (10)	−0.0008 (8)	0.0034 (8)	0.0013 (8)
C12A	0.0568 (13)	0.0344 (11)	0.0408 (10)	−0.0011 (10)	0.0012 (9)	0.0023 (8)
C13A	0.0693 (15)	0.0438 (13)	0.0464 (11)	−0.0047 (11)	0.0003 (10)	−0.0061 (10)
C14A	0.0574 (13)	0.0383 (13)	0.0618 (14)	−0.0052 (10)	0.0042 (10)	−0.0089 (10)
C15A	0.0555 (13)	0.0343 (12)	0.0639 (13)	−0.0018 (10)	0.0055 (10)	0.0062 (10)
C16A	0.0493 (12)	0.0364 (11)	0.0453 (11)	−0.0014 (9)	0.0035 (9)	0.0052 (9)
C21A	0.0387 (10)	0.0334 (11)	0.0381 (10)	0.0021 (8)	0.0033 (8)	−0.0004 (8)
C22A	0.0544 (12)	0.0344 (11)	0.0353 (9)	0.0040 (9)	0.0067 (8)	−0.0049 (8)
C23A	0.0582 (13)	0.0377 (12)	0.0343 (9)	0.0056 (9)	0.0098 (8)	0.0011 (8)
C24A	0.0386 (11)	0.0334 (11)	0.0364 (10)	0.0035 (8)	0.0026 (8)	0.0016 (8)
C25A	0.0498 (12)	0.0326 (11)	0.0387 (10)	0.0029 (9)	0.0009 (8)	−0.0051 (8)
C26A	0.0538 (12)	0.0390 (12)	0.0330 (9)	0.0031 (9)	0.0025 (8)	−0.0008 (8)

O1—C1	1.2326 (19)	O1A—C1A	1.235 (2)
O2—C24	1.366 (2)	O2A—C24A	1.363 (2)
O2—C4	1.438 (2)	O2A—C4A	1.432 (2)
C1—C2	1.470 (3)	C1A—C2A	1.466 (3)
C1—C11	1.496 (3)	C1A—C11A	1.500 (3)
C2—C3	1.338 (3)	C2A—C3A	1.332 (2)
C2—H2	0.9500	C2A—H2A	0.9500
C3—C21	1.459 (3)	C3A—C21A	1.459 (3)
C3—H3	0.9500	C3A—H3A	0.9500
C4—C5	1.505 (2)	C4A—C5A	1.507 (2)
C4—H4A	0.9900	C4A—H4A1	0.9900
C4—H4B	0.9900	C4A—H4A2	0.9900
C5—C6	1.520 (3)	C5A—C6A	1.522 (3)
C5—H5A	0.9900	C5A—H5A1	0.9900
C5—H5B	0.9900	C5A—H5A2	0.9900
C6—C7	1.518 (3)	C6A—C7A	1.515 (3)
C6—H6A	0.9900	C6A—H6A1	0.9900
C6—H6B	0.9900	C6A—H6A2	0.9900
C7—C8	1.516 (3)	C7A—C8A	1.525 (3)
C7—H7A	0.9900	C7A—H7A1	0.9900
C7—H7B	0.9900	C7A—H7A2	0.9900
C8—H8A	0.9800	C8A—H8A1	0.9800
C8—H8B	0.9800	C8A—H8A2	0.9800
C8—H8C	0.9800	C8A—H8A3	0.9800
C11—C16	1.388 (3)	C11A—C12A	1.389 (2)
C11—C12	1.393 (2)	C11A—C16A	1.393 (3)
C12—C13	1.387 (3)	C12A—C13A	1.383 (3)
C12—H12	0.9500	C12A—H12A	0.9500
C13—C14	1.377 (3)	C13A—C14A	1.376 (3)
C13—H13	0.9500	C13A—H13A	0.9500
C14—C15	1.384 (3)	C14A—C15A	1.377 (3)
C14—H14	0.9500	C14A—H14A	0.9500
C15—C16	1.379 (3)	C15A—C16A	1.384 (3)
C15—H15	0.9500	C15A—H15A	0.9500
C16—H16	0.9500	C16A—H16A	0.9500
C21—C26	1.393 (3)	C21A—C26A	1.394 (3)
C21—C22	1.406 (2)	C21A—C22A	1.399 (2)
C22—C23	1.372 (3)	C22A—C23A	1.375 (3)
C22—H22	0.9500	C22A—H22A	0.9500
C23—C24	1.394 (3)	C23A—C24A	1.387 (2)
C23—H23	0.9500	C23A—H23A	0.9500
C24—C25	1.388 (2)	C24A—C25A	1.394 (2)
C25—C26	1.380 (3)	C25A—C26A	1.384 (3)
C25—H25	0.9500	C25A—H25A	0.9500
C26—H26	0.9500	C26A—H26A	0.9500
C24—O2—C4	117.09 (13)	C24A—O2A—C4A	118.52 (13)
O1—C1—C2	121.27 (17)	O1A—C1A—C2A	121.18 (17)
O1—C1—C11	118.89 (16)	O1A—C1A—C11A	119.30 (17)
C2—C1—C11	119.83 (15)	C2A—C1A—C11A	119.52 (16)
C3—C2—C1	120.71 (16)	C3A—C2A—C1A	122.50 (16)
C3—C2—H2	119.6	C3A—C2A—H2A	118.8
C1—C2—H2	119.6	C1A—C2A—H2A	118.8
C2—C3—C21	128.96 (17)	C2A—C3A—C21A	127.02 (17)
C2—C3—H3	115.5	C2A—C3A—H3A	116.5
C21—C3—H3	115.5	C21A—C3A—H3A	116.5
O2—C4—C5	108.55 (14)	O2A—C4A—C5A	107.93 (14)
O2—C4—H4A	110.0	O2A—C4A—H4A1	110.1
C5—C4—H4A	110.0	C5A—C4A—H4A1	110.1
O2—C4—H4B	110.0	O2A—C4A—H4A2	110.1
C5—C4—H4B	110.0	C5A—C4A—H4A2	110.1
H4A—C4—H4B	108.4	H4A1—C4A—H4A2	108.4
C4—C5—C6	111.17 (15)	C4A—C5A—C6A	111.76 (15)
C4—C5—H5A	109.4	C4A—C5A—H5A1	109.3
C6—C5—H5A	109.4	C6A—C5A—H5A1	109.3
C4—C5—H5B	109.4	C4A—C5A—H5A2	109.3
C6—C5—H5B	109.4	C6A—C5A—H5A2	109.3
H5A—C5—H5B	108.0	H5A1—C5A—H5A2	107.9
C7—C6—C5	114.12 (15)	C7A—C6A—C5A	113.83 (16)
C7—C6—H6A	108.7	C7A—C6A—H6A1	108.8
C5—C6—H6A	108.7	C5A—C6A—H6A1	108.8
C7—C6—H6B	108.7	C7A—C6A—H6A2	108.8
C5—C6—H6B	108.7	C5A—C6A—H6A2	108.8
H6A—C6—H6B	107.6	H6A1—C6A—H6A2	107.7
C8—C7—C6	113.43 (17)	C6A—C7A—C8A	112.62 (19)
C8—C7—H7A	108.9	C6A—C7A—H7A1	109.1
C6—C7—H7A	108.9	C8A—C7A—H7A1	109.1
C8—C7—H7B	108.9	C6A—C7A—H7A2	109.1
C6—C7—H7B	108.9	C8A—C7A—H7A2	109.1
H7A—C7—H7B	107.7	H7A1—C7A—H7A2	107.8
C7—C8—H8A	109.5	C7A—C8A—H8A1	109.5
C7—C8—H8B	109.5	C7A—C8A—H8A2	109.5
H8A—C8—H8B	109.5	H8A1—C8A—H8A2	109.5
C7—C8—H8C	109.5	C7A—C8A—H8A3	109.5
H8A—C8—H8C	109.5	H8A1—C8A—H8A3	109.5
H8B—C8—H8C	109.5	H8A2—C8A—H8A3	109.5
C16—C11—C12	118.38 (17)	C12A—C11A—C16A	118.70 (18)
C16—C11—C1	118.33 (15)	C12A—C11A—C1A	123.21 (17)
C12—C11—C1	123.28 (16)	C16A—C11A—C1A	118.08 (16)
C13—C12—C11	120.51 (18)	C13A—C12A—C11A	120.43 (18)
C13—C12—H12	119.7	C13A—C12A—H12A	119.8
C11—C12—H12	119.7	C11A—C12A—H12A	119.8
C14—C13—C12	120.10 (18)	C14A—C13A—C12A	120.37 (19)
C14—C13—H13	119.9	C14A—C13A—H13A	119.8
C12—C13—H13	119.9	C12A—C13A—H13A	119.8
C13—C14—C15	120.05 (19)	C13A—C14A—C15A	119.9 (2)
C13—C14—H14	120.0	C13A—C14A—H14A	120.1
C15—C14—H14	120.0	C15A—C14A—H14A	120.1
C16—C15—C14	119.72 (19)	C14A—C15A—C16A	120.21 (19)
C16—C15—H15	120.1	C14A—C15A—H15A	119.9
C14—C15—H15	120.1	C16A—C15A—H15A	119.9
C15—C16—C11	121.22 (18)	C15A—C16A—C11A	120.40 (18)
C15—C16—H16	119.4	C15A—C16A—H16A	119.8
C11—C16—H16	119.4	C11A—C16A—H16A	119.8
C26—C21—C22	117.01 (17)	C26A—C21A—C22A	117.06 (17)
C26—C21—C3	119.03 (16)	C26A—C21A—C3A	120.60 (16)
C22—C21—C3	123.96 (17)	C22A—C21A—C3A	122.34 (16)
C23—C22—C21	121.11 (17)	C23A—C22A—C21A	121.41 (17)
C23—C22—H22	119.4	C23A—C22A—H22A	119.3
C21—C22—H22	119.4	C21A—C22A—H22A	119.3
C22—C23—C24	120.61 (17)	C22A—C23A—C24A	120.38 (17)
C22—C23—H23	119.7	C22A—C23A—H23A	119.8
C24—C23—H23	119.7	C24A—C23A—H23A	119.8
O2—C24—C25	124.47 (17)	O2A—C24A—C23A	115.34 (15)
O2—C24—C23	116.06 (15)	O2A—C24A—C25A	124.88 (16)
C25—C24—C23	119.47 (18)	C23A—C24A—C25A	119.78 (17)
C26—C25—C24	119.22 (17)	C26A—C25A—C24A	118.84 (17)
C26—C25—H25	120.4	C26A—C25A—H25A	120.6
C24—C25—H25	120.4	C24A—C25A—H25A	120.6
C25—C26—C21	122.57 (17)	C25A—C26A—C21A	122.49 (17)
C25—C26—H26	118.7	C25A—C26A—H26A	118.8
C21—C26—H26	118.7	C21A—C26A—H26A	118.8
O1—C1—C2—C3	3.2 (3)	O1A—C1A—C2A—C3A	9.5 (3)
C11—C1—C2—C3	−177.21 (17)	C11A—C1A—C2A—C3A	−170.05 (18)
C1—C2—C3—C21	−179.97 (18)	C1A—C2A—C3A—C21A	179.74 (18)
C24—O2—C4—C5	−178.53 (15)	C24A—O2A—C4A—C5A	−179.11 (16)
O2—C4—C5—C6	−175.23 (15)	O2A—C4A—C5A—C6A	−177.50 (16)
C4—C5—C6—C7	−178.06 (17)	C4A—C5A—C6A—C7A	177.72 (17)
C5—C6—C7—C8	−175.46 (18)	C5A—C6A—C7A—C8A	−176.95 (18)
O1—C1—C11—C16	−12.6 (3)	O1A—C1A—C11A—C12A	170.93 (18)
C2—C1—C11—C12	−13.4 (3)	C2A—C1A—C11A—C12A	−9.5 (3)
C2—C1—C11—C16	167.85 (17)	O1A—C1A—C11A—C16A	−8.0 (3)
O1—C1—C11—C12	166.19 (17)	C2A—C1A—C11A—C16A	171.52 (17)
C16—C11—C12—C13	0.0 (3)	C16A—C11A—C12A—C13A	0.8 (3)
C1—C11—C12—C13	−178.79 (18)	C1A—C11A—C12A—C13A	−178.11 (19)
C11—C12—C13—C14	0.7 (3)	C11A—C12A—C13A—C14A	−1.0 (3)
C12—C13—C14—C15	−1.1 (3)	C12A—C13A—C14A—C15A	0.1 (3)
C13—C14—C15—C16	0.8 (3)	C13A—C14A—C15A—C16A	1.0 (3)
C14—C15—C16—C11	−0.2 (3)	C14A—C15A—C16A—C11A	−1.2 (3)
C12—C11—C16—C15	−0.2 (3)	C12A—C11A—C16A—C15A	0.3 (3)
C1—C11—C16—C15	178.60 (18)	C1A—C11A—C16A—C15A	179.26 (18)
C2—C3—C21—C26	177.7 (2)	C2A—C3A—C21A—C26A	178.60 (19)
C2—C3—C21—C22	−1.8 (3)	C2A—C3A—C21A—C22A	−1.5 (3)
C26—C21—C22—C23	0.3 (3)	C26A—C21A—C22A—C23A	−0.1 (3)
C3—C21—C22—C23	179.79 (19)	C3A—C21A—C22A—C23A	−179.92 (18)
C21—C22—C23—C24	0.0 (3)	C21A—C22A—C23A—C24A	−1.6 (3)
C4—O2—C24—C25	5.0 (3)	C4A—O2A—C24A—C23A	178.06 (17)
C4—O2—C24—C23	−175.43 (17)	C4A—O2A—C24A—C25A	−2.0 (3)
C22—C23—C24—O2	−179.33 (17)	C22A—C23A—C24A—O2A	−178.06 (17)
C22—C23—C24—C25	0.3 (3)	C22A—C23A—C24A—C25A	2.0 (3)
O2—C24—C25—C26	178.69 (18)	O2A—C24A—C25A—C26A	179.28 (17)
C23—C24—C25—C26	−0.9 (3)	C23A—C24A—C25A—C26A	−0.8 (3)
C24—C25—C26—C21	1.2 (3)	C24A—C25A—C26A—C21A	−0.9 (3)
C22—C21—C26—C25	−0.9 (3)	C22A—C21A—C26A—C25A	1.3 (3)
C3—C21—C26—C25	179.55 (18)	C3A—C21A—C26A—C25A	−178.83 (18)

Table 1

Selected torsion angles (°)

C11—C1—C2—C3	−177.21 (17)
C2—C1—C11—C12	−13.4 (3)
C2—C1—C11—C16	167.85 (17)
C11A—C1A—C2A—C3A	−170.05 (18)
C2A—C1A—C11A—C12A	−9.5 (3)
C2A—C1A—C11A—C16A	171.52 (17)