1,2,3-Trimeth­oxy-4-[(E)-2-phenyl­vinyl]benzene and (E,E)-1,4-bis­(2,3,4-trimethoxy­phenyl)buta-1,3-diene

The stilbene derivative 1,2,3-trimeth­oxy-4-[(E)-2-phenyl­vinyl]benzene, C₁₇H₁₈O₃, (I), and its homocoupling co-product (E,E)-1,4-bis­(2,3,4-trimethoxy­phenyl)buta-1,3-diene, C₂₂H₂₆O₆, (II), both have double bonds in trans conformations in their conjugated linkages. In the structure of stilbene (I), the aromatic rings deviate significantly from coplanarity, in contrast with coproduct (II), the core of which is rigorously planar. The deviation in stilbene (I) seems to be driven by inter­molecular electrostatic inter­actions. Diene (II) sits on a crystallographic inversion centre, which bis­ects the conjugated linkage.

S1. Comment

Stilbenes are important core structures and their photochemical [photooxygenation (Kwon et al., 1989)] and photophysical properties [photoisomerization (Waldeck, 1991), fluorescence (Chaudhuri & Ganguly, 1969; Singh & Kanvah, 2001), photochromic activity (Irie et al., 1994; Lucas et al., 1998)] have been widely studied in connection with π–π* electronic transitions of the C═C double bound. Stilbenes can exist as two possible isomers, trans-stilbene and cis-stilbene. The cis series, for example, is involved in the combretastatin derivatives, compounds that display cytotoxic activities against a wide range of human cancers (Pettit et al., 2005). Stilbenes are not only used as dyes and in optics (lasers), but are also of interest from a medical point of view (Heynekamp et al., 2006; Sanoh et al., 2006; Vander Jagt & Deck, 2007).

Other natural products, derived from trans-stilbenes such as resveratrol and its analogues, exhibit important biological activities. Indeed, trans-resveratrol is known to possess antioxidant and anti-inflammatory properties and is antiproliferative with pro-apoptotic effects (Baur & Sinclair, 2006).

We have previously reported a synthesis of trans-1,2-diarylethenes (trans-stilbenes), compounds having potential photoprotective properties. They were synthesized from trans-cinnamic acids using a strategy combining Hunsdiecker-type bromodecarboxylation and the Suzuki cross-coupling reaction under microwave heating (Bazin et al., 2007). Bromodecarboxylation starting from 2,3,4-trimethoxycinnamic acid gave the corresponding β-bromostyrene intermediate, which allowed the Suzuki cross-coupling reaction with phenylboronic acid. The desired stilbene, (I), was obtained in 71% yield and we also observed 1,4-diarylbuta-1,3-diene, (II), as an unexpected homocoupling by-product (8% yield).

The asymmetric unit of compound (I) (Fig. 1a) contains one molecule and that of compound (II) (Fig. 1c) contains one half molecule, the remainder of (II) being generated by the symmetry centre situated at the midpoint of C8—C8ⁱ in the conjugated linkage [symmetry code: (i) -x, -y, -z].

For both compounds, the double bonds in the conjugated linkage are in the trans configuration. Futhermore, the observed double bonds are longer and the single bonds shorter (Tables 1 and 2) than the theoretical values (1.32 Å for double bonds and 1.51 Å for single bonds; Glusker et al., 1994), indicating the formation of a weak conjugated π-electron system.

In the stilbene structure, (I), the aromatic rings deviate significantly from a coplanar arrangement, with a dihedral angle of 16.92 (3)°. The origin of this deviation seems to be an intermolecular interaction occurring between neighbouring molecules rather than internal steric hindrance. A contact is observed between the benzene ring C11—H11 and atom O3ⁱⁱ of the methoxy group of a neighbouring molecule [symmetry code: (ii) -1/2 + x, 1/2 - y, 1/2 + z], with H11···O3ⁱⁱ = 2.473 (12) Å, C11···O3ⁱⁱ = 3.457 (1) ° and C11—H11···O3ⁱⁱ 173.6 (9)°. Among the three methoxy substituents of each aromatic ring, only that at C4 is approximately coplanar with the aromatic ring; the other two, at C5 and C6, are oriented towards opposite sides of the aromatic ring (Fig. 1b).

The core of the co-product structure, (II), is rigorously planar, as the two halves are related by a symmetry centre. As in compound (I), only one of the three methoxy substituents is approximately coplanar with the aromatic ring. The other two are again out of the plane on opposite sides.

In stilbene (I) there are two nearly edge-on (or T-shaped) stacking contacts (Fig. 2), one involving each of the two aromatic rings. Atom H14 of the unsubstituted phenyl is oriented toward the centroid Cg1ⁱ of its neighbour [symmetry code: (i) -1/2 - x, 1/2 + y, 1/2 - z], with H14···Cg1ⁱ = 2.765 (11) Å and C14—H14···.Cg1ⁱ = 136.2 (9)°. The second contact, between atom H8 of the double-bonded fragment and the substituted phenyl of a neighbour, is weak but appears to be directed; H8···Cg2ⁱⁱⁱ = 3.23 (13) Å and C8—H8···Cg2ⁱⁱⁱ = 166.7 (10)° [symmetry code: (iii) 1/2 - x, -1/2 + y, 1/2 - z]. As we have already described, a weak electrostatic H11···O3ⁱⁱ interaction is also present.

In the extended structure of co-product (II), only one significant contact was found, which consists of a T-shaped stacking interaction between the aromatic rings. C2—H2 contacts the centroid Cg1ⁱ of a neighbouring ring [symmetry code: (i) 1/2 - x, -1/2 + y, 1/2 - z], with H2···Cg1ⁱ = 2.837 (15) Å and C2—H2···Cg1ⁱ = 154.6 (11)°.

[Please define all Cg in terms of atom labels.]

S2. Experimental

Compounds (I) and (II) were prepared according to the literature procedure of Bazin et al. (2007). Compound (II) was isolated as the homocoupling by-product. Compound (I) was recrystallized from methanol to afford pure (I) as white [Colourless in CIF] crystals (m.p. 355 K). Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz, δ, p.p.m.): 3.89 (s, 3H, –OMe), 3.90 (s, 3H, –OMe), 3.91 (s, 3H, –OMe), 6.71 (d, 1H, J = 8.8 Hz), 7.03 (d, 1H, J = 16.6 Hz), 7.24–7.37 (m, 5H), 7.51–7.53 (m, 2H); ¹³C NMR (CDCl₃, 100 MHz, δ, p.p.m.): 56.0 (–OMe), 60.9 (–OMe), 61.3 (–OMe), 107.8, 120.7, 122.9, 124.5, 126.4 (2 C), 127.2, 127.9, 128.6 (2 C), 137.9, 142.4, 151.7, 153.2; MS (ESI): [M+H]⁺ 271. Compound (II) was recrystallized by slow evaporation of a cyclohexane/ethyl acetate [Solvent ratio?] solution, giving yellow [Colourless in CIF] crystals of (II) after 1 or 2 d. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz, δ, p.p.m.): 3.87, 3.88 and 3.89 (3s, 18H, 6-OMe), 6.41–6.54 (m, 2H), 6.63–6.70 (m, 2H), 6.87–6.90 (m, 1H), 7.12–7.23 (m, 3H); MS (ESI): [M+H]⁺ 387.

S3. Refinement

All H atoms were determined via difference Fourier maps and refined with isotropic atomic displacement parameters. [Please give range of refined C—H distances]

Computing details

For both compounds, data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. (a) and (b). Mutually perpendicular views of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small circles of arbitrary radii. (c) Molecular structure of (II) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry code: (i) -x, -y, -z.]
	Fig. 2. A view of the stacking interactions (dashed lines) in stilbene (I). [Symmetry codes: (i) -1/2 - x, 1/2 + y, 1/2 - z; (ii) -1/2 + x, 1/2 - y, 1/2 + z; (iii) 1/2 - x, -1/2 + y, 1/2 - z.]
	Fig. 3. [Please provide caption]

(I) 1,2,3-Trimethoxy-4-[(E)-2-phenylvinyl]benzene

Crystal data

C17H18O3	F(000) = 576
Mr = 270.31	Dx = 1.231 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9739 reflections
a = 10.7138 (7) Å	θ = 2.5–36.0°
b = 7.1069 (5) Å	µ = 0.08 mm^−1
c = 19.8033 (13) Å	T = 296 K
β = 104.760 (3)°	Plate, colourless
V = 1458.10 (17) Å^3	0.52 × 0.37 × 0.25 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	5406 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.027
Graphite monochromator	θmax = 35.0°, θmin = 2.0°
ϕ and ω scans	h = −16→17
66478 measured reflections	k = −11→11
6392 independent reflections	l = −31→31

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: difference Fourier map
wR(F^2) = 0.122	All H-atom parameters refined
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0729P)^2 + 0.2108P] where P = (Fo^2 + 2Fc^2)/3
6392 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.63 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.14291 (6)	0.47639 (8)	0.16862 (3)	0.01361 (10)
C2	0.23922 (6)	0.33830 (9)	0.18580 (3)	0.01582 (11)
H2	0.2361 (11)	0.2457 (16)	0.2228 (6)	0.022 (2)*
C3	0.33426 (6)	0.31824 (9)	0.14994 (3)	0.01656 (11)
H3	0.4022 (11)	0.2228 (17)	0.1645 (6)	0.027 (3)*
C4	0.33371 (6)	0.43529 (8)	0.09331 (3)	0.01398 (10)
C5	0.23913 (5)	0.57579 (8)	0.07491 (3)	0.01343 (10)
C6	0.14696 (5)	0.59793 (8)	0.11299 (3)	0.01333 (10)
C7	0.03922 (6)	0.49449 (8)	0.20434 (3)	0.01495 (11)
H7	−0.0253 (11)	0.5923 (16)	0.1849 (6)	0.024 (3)*
C8	0.02736 (6)	0.38905 (9)	0.25873 (3)	0.01576 (11)
H8	0.0932 (12)	0.2921 (19)	0.2796 (7)	0.035 (3)*
C9	−0.07715 (6)	0.39765 (8)	0.29423 (3)	0.01448 (10)
C10	−0.06031 (6)	0.30219 (10)	0.35774 (3)	0.01853 (12)
H10	0.0218 (11)	0.2408 (17)	0.3789 (6)	0.028 (3)*
C11	−0.15615 (7)	0.30006 (10)	0.39362 (3)	0.02069 (12)
H11	−0.1400 (11)	0.2281 (17)	0.4377 (6)	0.027 (3)*
C12	−0.27147 (7)	0.39405 (10)	0.36657 (4)	0.02157 (13)
H12	−0.3388 (12)	0.3902 (18)	0.3924 (6)	0.033 (3)*
C13	−0.29003 (7)	0.48988 (11)	0.30344 (4)	0.02386 (14)
H13	−0.3715 (13)	0.5524 (19)	0.2817 (7)	0.037 (3)*
C14	−0.19428 (6)	0.49194 (10)	0.26734 (4)	0.01983 (12)
H14	−0.2121 (11)	0.5589 (16)	0.2220 (6)	0.026 (3)*
O1	0.05531 (4)	0.73719 (7)	0.09349 (3)	0.01729 (10)
C15	0.10639 (8)	0.92301 (10)	0.11076 (5)	0.02610 (15)
H15A	0.0376 (14)	1.010 (2)	0.0899 (7)	0.045 (4)*
H15B	0.1303 (17)	0.940 (2)	0.1641 (9)	0.070 (5)*
H15C	0.1811 (13)	0.9449 (19)	0.0938 (7)	0.040 (3)*
O2	0.24124 (4)	0.69496 (7)	0.02055 (2)	0.01632 (9)
C16	0.15007 (7)	0.64190 (11)	−0.04315 (3)	0.02276 (13)
H16A	0.1667 (11)	0.7272 (17)	−0.0786 (6)	0.029 (3)*
H16B	0.1671 (12)	0.5092 (19)	−0.0577 (7)	0.038 (3)*
H16C	0.0608 (12)	0.6544 (18)	−0.0386 (7)	0.033 (3)*
O3	0.41951 (5)	0.42633 (7)	0.05340 (2)	0.01679 (10)
C17	0.52332 (8)	0.29419 (12)	0.07398 (4)	0.02635 (15)
H17A	0.4905 (12)	0.1651 (18)	0.0716 (6)	0.034 (3)*
H17B	0.5762 (12)	0.3230 (18)	0.1204 (6)	0.031 (3)*
H17C	0.5735 (11)	0.3116 (17)	0.0392 (6)	0.032 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0145 (2)	0.0134 (2)	0.0134 (2)	−0.00109 (17)	0.00449 (17)	0.00001 (17)
C2	0.0180 (2)	0.0160 (2)	0.0146 (2)	0.00184 (19)	0.00626 (19)	0.00274 (18)
C3	0.0185 (2)	0.0163 (2)	0.0162 (2)	0.00356 (19)	0.00678 (19)	0.00339 (19)
C4	0.0143 (2)	0.0149 (2)	0.0135 (2)	0.00065 (18)	0.00482 (17)	0.00072 (18)
C5	0.0134 (2)	0.0137 (2)	0.0132 (2)	−0.00054 (17)	0.00350 (17)	0.00195 (17)
C6	0.0126 (2)	0.0129 (2)	0.0145 (2)	−0.00028 (17)	0.00339 (17)	0.00099 (17)
C7	0.0155 (2)	0.0152 (2)	0.0150 (2)	−0.00097 (18)	0.00554 (18)	−0.00045 (18)
C8	0.0149 (2)	0.0174 (2)	0.0159 (2)	−0.00015 (19)	0.00551 (18)	0.00145 (19)
C9	0.0150 (2)	0.0140 (2)	0.0152 (2)	−0.00095 (18)	0.00524 (18)	0.00076 (18)
C10	0.0174 (3)	0.0211 (3)	0.0178 (2)	0.0008 (2)	0.0057 (2)	0.0049 (2)
C11	0.0224 (3)	0.0237 (3)	0.0179 (2)	−0.0022 (2)	0.0087 (2)	0.0032 (2)
C12	0.0221 (3)	0.0204 (3)	0.0266 (3)	−0.0005 (2)	0.0142 (2)	0.0010 (2)
C13	0.0198 (3)	0.0229 (3)	0.0322 (3)	0.0054 (2)	0.0126 (3)	0.0081 (3)
C14	0.0177 (3)	0.0210 (3)	0.0223 (3)	0.0029 (2)	0.0078 (2)	0.0072 (2)
O1	0.01418 (19)	0.01464 (19)	0.0234 (2)	0.00198 (14)	0.00547 (16)	0.00408 (16)
C15	0.0252 (3)	0.0144 (3)	0.0400 (4)	0.0017 (2)	0.0107 (3)	0.0009 (3)
O2	0.01591 (19)	0.0180 (2)	0.01482 (18)	−0.00124 (15)	0.00357 (15)	0.00482 (15)
C16	0.0249 (3)	0.0255 (3)	0.0153 (2)	−0.0006 (2)	0.0005 (2)	0.0040 (2)
O3	0.01709 (19)	0.0189 (2)	0.01663 (19)	0.00391 (15)	0.00838 (15)	0.00314 (15)
C17	0.0245 (3)	0.0314 (4)	0.0275 (3)	0.0135 (3)	0.0146 (3)	0.0116 (3)

Geometric parameters (Å, º)

C1—C2	1.4017 (9)	C11—C12	1.3865 (10)
C1—C6	1.4093 (8)	C11—H11	0.989 (12)
C1—C7	1.4667 (8)	C12—C13	1.3926 (10)
C2—C3	1.3893 (8)	C12—H12	0.986 (12)
C2—H2	0.991 (11)	C13—C14	1.3919 (9)
C3—C4	1.3951 (8)	C13—H13	0.977 (13)
C3—H3	0.983 (12)	C14—H14	0.991 (11)
C4—O3	1.3578 (7)	O1—C15	1.4370 (9)
C4—C5	1.4030 (8)	C15—H15A	0.970 (14)
C5—O2	1.3745 (7)	C15—H15B	1.028 (17)
C5—C6	1.3956 (8)	C15—H15C	0.956 (13)
C6—O1	1.3783 (7)	O2—C16	1.4351 (8)
C7—C8	1.3445 (8)	C16—H16A	0.979 (12)
C7—H7	0.987 (11)	C16—H16B	1.016 (13)
C8—C9	1.4673 (8)	C16—H16C	0.987 (12)
C8—H8	0.998 (13)	O3—C17	1.4332 (8)
C9—C10	1.3997 (8)	C17—H17A	0.980 (13)
C9—C14	1.4024 (9)	C17—H17B	0.971 (12)
C10—C11	1.3896 (9)	C17—H17C	0.983 (12)
C10—H10	0.975 (12)
C2—C1—C6	116.84 (5)	C10—C11—H11	118.1 (7)
C2—C1—C7	123.06 (5)	C11—C12—C13	119.47 (6)
C6—C1—C7	120.08 (5)	C11—C12—H12	118.9 (7)
C3—C2—C1	122.54 (5)	C13—C12—H12	121.6 (7)
C3—C2—H2	118.4 (6)	C14—C13—C12	120.71 (6)
C1—C2—H2	118.9 (6)	C14—C13—H13	117.5 (7)
C2—C3—C4	119.75 (6)	C12—C13—H13	121.8 (7)
C2—C3—H3	120.3 (7)	C13—C14—C9	120.35 (6)
C4—C3—H3	119.9 (7)	C13—C14—H14	118.2 (6)
O3—C4—C3	125.10 (5)	C9—C14—H14	121.4 (6)
O3—C4—C5	115.69 (5)	C6—O1—C15	113.10 (5)
C3—C4—C5	119.21 (5)	O1—C15—H15A	106.4 (9)
O2—C5—C6	120.58 (5)	O1—C15—H15B	109.3 (10)
O2—C5—C4	119.14 (5)	H15A—C15—H15B	109.2 (13)
C6—C5—C4	120.24 (5)	O1—C15—H15C	111.6 (8)
O1—C6—C5	118.77 (5)	H15A—C15—H15C	111.1 (11)
O1—C6—C1	119.82 (5)	H15B—C15—H15C	109.3 (12)
C5—C6—C1	121.35 (5)	C5—O2—C16	112.53 (5)
C8—C7—C1	125.12 (6)	O2—C16—H16A	105.1 (7)
C8—C7—H7	120.4 (6)	O2—C16—H16B	111.2 (7)
C1—C7—H7	114.5 (6)	H16A—C16—H16B	107.0 (10)
C7—C8—C9	126.87 (6)	O2—C16—H16C	110.7 (7)
C7—C8—H8	121.0 (7)	H16A—C16—H16C	111.6 (10)
C9—C8—H8	112.1 (7)	H16B—C16—H16C	111.0 (11)
C10—C9—C14	118.09 (6)	C4—O3—C17	117.17 (5)
C10—C9—C8	118.10 (5)	O3—C17—H17A	110.9 (7)
C14—C9—C8	123.80 (5)	O3—C17—H17B	110.8 (7)
C11—C10—C9	121.45 (6)	H17A—C17—H17B	111.0 (10)
C11—C10—H10	118.5 (7)	O3—C17—H17C	104.0 (7)
C9—C10—H10	119.9 (7)	H17A—C17—H17C	109.8 (10)
C12—C11—C10	119.93 (6)	H17B—C17—H17C	110.2 (10)
C12—C11—H11	121.9 (7)

(II) (E,E)-1,4-bis(2,3,4-trimethoxyphenyl)buta-1,3-diene

Crystal data

C22H26O6	F(000) = 412
Mr = 386.43	Dx = 1.299 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9216 reflections
a = 10.2899 (4) Å	θ = 2.3–36.3°
b = 7.0186 (3) Å	µ = 0.09 mm^−1
c = 13.9897 (5) Å	T = 296 K
β = 102.138 (2)°	Plate, colourless
V = 987.76 (7) Å^3	0.32 × 0.21 × 0.18 mm
Z = 2

Data collection

Bruker APEXII CCD area-detector diffractometer	3409 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.053
Graphite monochromator	θmax = 35.0°, θmin = 2.3°
ϕ and ω scans	h = −16→16
30080 measured reflections	k = −11→10
4333 independent reflections	l = −21→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: difference Fourier map
wR(F^2) = 0.136	All H-atom parameters refined
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0829P)^2 + 0.1139P] where P = (Fo^2 + 2Fc^2)/3
4333 reflections	(Δ/σ)max < 0.001
179 parameters	Δρmax = 0.68 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.28922 (7)	0.06584 (11)	0.12655 (6)	0.01294 (14)
C2	0.29912 (8)	−0.06337 (11)	0.20410 (6)	0.01579 (15)
H2	0.2234 (14)	−0.150 (2)	0.2091 (10)	0.021 (3)*
C3	0.41067 (8)	−0.07076 (11)	0.27982 (6)	0.01584 (15)
H3	0.4118 (14)	−0.161 (2)	0.3324 (10)	0.026 (3)*
C4	0.51690 (7)	0.05351 (11)	0.28063 (6)	0.01356 (14)
C5	0.51088 (7)	0.18244 (10)	0.20317 (6)	0.01276 (14)
C6	0.39819 (7)	0.18788 (10)	0.12767 (5)	0.01247 (14)
C7	0.17092 (7)	0.08541 (11)	0.04843 (6)	0.01402 (14)
H7	0.1750 (14)	0.1769 (19)	−0.0002 (10)	0.021 (3)*
C8	0.05752 (7)	−0.01658 (11)	0.03862 (5)	0.01399 (14)
H8	0.0492 (13)	−0.117 (2)	0.0854 (9)	0.022 (3)*
O1	0.39277 (6)	0.32140 (8)	0.05491 (4)	0.01553 (13)
C9	0.45411 (10)	0.25947 (14)	−0.02267 (7)	0.02239 (18)
H9A	0.5473 (15)	0.221 (2)	0.0032 (11)	0.034 (4)*
H9B	0.4567 (15)	0.365 (2)	−0.0674 (11)	0.029 (3)*
H9C	0.4056 (15)	0.149 (2)	−0.0570 (10)	0.030 (4)*
O2	0.61634 (6)	0.30017 (8)	0.19888 (4)	0.01464 (12)
C10	0.62063 (9)	0.46692 (12)	0.25903 (6)	0.01910 (16)
H10A	0.6370 (15)	0.4368 (19)	0.3281 (11)	0.026 (3)*
H10B	0.5335 (15)	0.533 (2)	0.2442 (11)	0.033 (4)*
H10C	0.6886 (13)	0.542 (2)	0.2437 (9)	0.021 (3)*
O3	0.62882 (6)	0.06182 (9)	0.35277 (4)	0.01632 (13)
C11	0.64741 (9)	−0.08735 (12)	0.42413 (6)	0.01779 (16)
H11C	0.5806 (15)	−0.085 (2)	0.4615 (10)	0.025 (3)*
H11A	0.7306 (15)	−0.056 (2)	0.4665 (11)	0.031 (4)*
H11B	0.6526 (14)	−0.211 (2)	0.3929 (10)	0.026 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0130 (3)	0.0113 (3)	0.0140 (3)	−0.0013 (2)	0.0015 (2)	−0.0003 (2)
C2	0.0148 (3)	0.0147 (3)	0.0169 (3)	−0.0041 (2)	0.0009 (2)	0.0025 (2)
C3	0.0155 (3)	0.0145 (3)	0.0165 (3)	−0.0032 (2)	0.0009 (2)	0.0033 (2)
C4	0.0133 (3)	0.0124 (3)	0.0140 (3)	−0.0009 (2)	0.0006 (2)	0.0006 (2)
C5	0.0123 (3)	0.0104 (3)	0.0154 (3)	−0.0017 (2)	0.0028 (2)	0.0002 (2)
C6	0.0136 (3)	0.0100 (3)	0.0136 (3)	−0.0004 (2)	0.0024 (2)	0.0008 (2)
C7	0.0135 (3)	0.0134 (3)	0.0142 (3)	−0.0013 (2)	0.0009 (2)	−0.0004 (2)
C8	0.0137 (3)	0.0135 (3)	0.0140 (3)	−0.0008 (2)	0.0014 (2)	−0.0018 (2)
O1	0.0184 (3)	0.0122 (3)	0.0158 (3)	−0.00030 (19)	0.0032 (2)	0.00383 (19)
C9	0.0308 (4)	0.0200 (4)	0.0179 (4)	−0.0025 (3)	0.0087 (3)	0.0018 (3)
O2	0.0136 (2)	0.0126 (2)	0.0181 (3)	−0.00376 (18)	0.00403 (19)	−0.00145 (19)
C10	0.0238 (4)	0.0144 (3)	0.0197 (4)	−0.0065 (3)	0.0060 (3)	−0.0031 (3)
O3	0.0146 (2)	0.0151 (3)	0.0167 (3)	−0.00239 (19)	−0.00243 (19)	0.00352 (19)
C11	0.0188 (3)	0.0159 (3)	0.0169 (3)	0.0002 (3)	−0.0002 (3)	0.0035 (3)

Geometric parameters (Å, º)

C1—C2	1.4012 (11)	C8—C8^i	1.4441 (14)
C1—C6	1.4085 (10)	C8—H8	0.977 (14)
C1—C7	1.4614 (10)	O1—C9	1.4330 (11)
C2—C3	1.3896 (11)	C9—H9A	0.988 (15)
C2—H2	1.001 (14)	C9—H9B	0.973 (16)
C3—C4	1.3966 (11)	C9—H9C	0.992 (16)
C3—H3	0.967 (14)	O2—C10	1.4367 (10)
C4—O3	1.3637 (9)	C10—H10A	0.968 (15)
C4—C5	1.4032 (11)	C10—H10B	0.992 (16)
C5—O2	1.3752 (9)	C10—H10C	0.935 (14)
C5—C6	1.3952 (10)	O3—C11	1.4314 (10)
C6—O1	1.3761 (9)	C11—H11C	0.947 (15)
C7—C8	1.3511 (11)	C11—H11A	0.958 (15)
C7—H7	0.943 (13)	C11—H11B	0.979 (14)
C2—C1—C6	117.19 (7)	C8^i—C8—H8	116.3 (8)
C2—C1—C7	123.60 (7)	C6—O1—C9	113.45 (6)
C6—C1—C7	119.15 (7)	O1—C9—H9A	110.7 (9)
C3—C2—C1	121.89 (7)	O1—C9—H9B	109.4 (9)
C3—C2—H2	117.0 (8)	H9A—C9—H9B	106.6 (12)
C1—C2—H2	121.0 (8)	O1—C9—H9C	110.3 (9)
C2—C3—C4	120.16 (7)	H9A—C9—H9C	108.4 (13)
C2—C3—H3	118.7 (9)	H9B—C9—H9C	111.4 (12)
C4—C3—H3	121.1 (9)	C5—O2—C10	113.04 (6)
O3—C4—C3	124.78 (7)	O2—C10—H10A	112.6 (8)
O3—C4—C5	115.93 (7)	O2—C10—H10B	110.2 (9)
C3—C4—C5	119.29 (7)	H10A—C10—H10B	105.7 (12)
O2—C5—C6	119.23 (7)	O2—C10—H10C	104.8 (8)
O2—C5—C4	120.94 (7)	H10A—C10—H10C	111.7 (12)
C6—C5—C4	119.80 (7)	H10B—C10—H10C	112.0 (12)
O1—C6—C5	118.46 (6)	C4—O3—C11	116.94 (6)
O1—C6—C1	119.84 (7)	O3—C11—H11C	111.6 (9)
C5—C6—C1	121.65 (7)	O3—C11—H11A	103.7 (9)
C8—C7—C1	126.30 (7)	H11C—C11—H11A	108.3 (12)
C8—C7—H7	117.1 (8)	O3—C11—H11B	110.5 (8)
C1—C7—H7	116.6 (8)	H11C—C11—H11B	112.0 (12)
C7—C8—C8^i	123.04 (9)	H11A—C11—H11B	110.5 (12)
C7—C8—H8	120.6 (8)

Symmetry code: (i) −x, −y, −z.