Ethyl 3-(4-geranyl­oxy-3-methoxy­phenyl)-2-propenoate

Miyake, Y.; Hosoda, A.; Nomura, E.; Taniguchi, H.

doi:10.1107/S1600536801017184

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Ethyl 3-(4-geranyloxy-3-methoxyphenyl)-2-propenoate

Y. Miyake, A. Hosoda, E. Nomura and H. Taniguchi

The title compound, C₂₂H₃₀O₄, is known as a chemopreventive agent against colon tumor development. The molecular structure is nearly planar, showing a trans arrangement with respect to the C=C bond of the phenylpropenoate moiety.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801017184/ob6063sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801017184/ob6063Isup2.hkl Contains datablock I

CCDC reference: 176031

checkCIF report

Key indicators

Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.003 Å
R factor = 0.059
wR factor = 0.120
Data-to-parameter ratio = 10.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           68.23
         From the CIF: _reflns_number_total               3429
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         3750
         Completeness (_total/calc)             91.44%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

The title compound, (I), is known as a chemopreventive agent against colon tumor development (Tsuda et al., 1999). It was prepared from ferulic acid, which was easily prepared in large quantities from the oily component of rice bran (Taniguchi et al., 1996).

The molecular structure of (I) is shown in Fig. 1, confirming the trans arrangement with respect to the C7═C8 double bond, similar to ferulic acid (Nethaji et al., 1988). The orientations of the phenyl ring and the geranyl group are defined by the torsion angles in Table 1. The molecule is nearly planar. The molecules in the crystal lattice are in a conventional herring-bone-type arrangement (Fig. 2). No close contacts were found that indicated any relevant intermolecular interaction.

Experimental top

To a solution of 1.0 g (4.5 mmol) of ethyl ferulate, ethyl ester of ferulic acid, 1.2 g (4.6 mmol) of triphenylphosphine and 0.69 g (4.5 mmol) of geraniol in 10 ml anhydrous tetrahydrofuran was added 0.93 g (4.6 mmol) diisopropyl azodicarboxylate. The mixture was stirred for 5 min at room temperature and the solvent then removed under reduced pressure. After the residue was extructed with 30 ml of hexane, hexane was moved under reduced pressure. Recrystallization from methanol gave the pure title compound (I) (1.37 g, 85%). Crystals of (I) were obtained by slow evaporation of an ethanol solution at 277–279 K.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

Figures top

	Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids
	Fig. 2. Projection down the c axis of the unit cell of (I)

(I) top

Crystal data top

C₂₂H₃₀O₄	Z = 2
M_r = 358.48	D_x = 1.164 Mg m⁻³
Triclinic, P1	Melting point: 30 K
a = 11.094 (1) Å	Cu Kα radiation, λ = 1.5418 Å
b = 11.943 (1) Å	Cell parameters from 2787 reflections
c = 9.3399 (9) Å	θ = 4.1–67.5°
α = 110.864 (5)°	µ = 0.63 mm⁻¹
β = 113.510 (5)°	T = 193 K
γ = 68.358 (4)°	Prism, colorless
V = 1022.5 (2) Å³	0.60 × 0.58 × 0.30 mm

Data collection top

Rigaku R-AXIS-RAPID Imaging Plate diffractometer	3094 reflections with F² > 2.0σ(F²)
ω scans	R_int = 0.028
Absorption correction: multi-scan (Higashi, 1995)	θ_max = 68.2°
T_min = 0.587, T_max = 0.828	h = −13→13
5896 measured reflections	k = −14→14
3429 independent reflections	l = −11→11

Refinement top

Refinement on F	w = 1/[σ²(F_o) + 0.00403\|F_o\|²]
R[F² > 2σ(F²)] = 0.059	(Δ/σ)_max = 0.0003
wR(F²) = 0.121	Δρ_max = 0.51 e Å⁻³
S = 1.65	Δρ_min = −0.28 e Å⁻³
3429 reflections	Extinction correction: Zachariasen (1967) type 2 Gaussian isotropic
326 parameters	Extinction coefficient: 0.39 (6)
H-atom parameters constrained

Crystal data top

C₂₂H₃₀O₄	γ = 68.358 (4)°
M_r = 358.48	V = 1022.5 (2) Å³
Triclinic, P1	Z = 2
a = 11.094 (1) Å	Cu Kα radiation
b = 11.943 (1) Å	µ = 0.63 mm⁻¹
c = 9.3399 (9) Å	T = 193 K
α = 110.864 (5)°	0.60 × 0.58 × 0.30 mm
β = 113.510 (5)°

Data collection top

Rigaku R-AXIS-RAPID Imaging Plate diffractometer	3429 independent reflections
Absorption correction: multi-scan (Higashi, 1995)	3094 reflections with F² > 2.0σ(F²)
T_min = 0.587, T_max = 0.828	R_int = 0.028
5896 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	326 parameters
wR(F²) = 0.121	H-atom parameters constrained
S = 1.65	Δρ_max = 0.51 e Å⁻³
3429 reflections	Δρ_min = −0.28 e Å⁻³

Special details top

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O(1)	0.8530 (1)	0.0444 (1)	0.1403 (1)	0.0467 (3)
O(2)	0.8930 (1)	0.1259 (1)	0.4481 (1)	0.0546 (4)
O(3)	0.4090 (2)	0.8420 (1)	0.3123 (2)	0.0794 (5)
O(4)	0.4986 (1)	0.7857 (1)	0.5440 (1)	0.0526 (4)
C(1)	0.7934 (2)	0.1665 (2)	0.1929 (2)	0.0432 (4)
C(2)	0.8137 (2)	0.2121 (2)	0.3608 (2)	0.0449 (4)
C(3)	0.7531 (2)	0.3341 (2)	0.4220 (2)	0.0458 (4)
C(4)	0.6724 (2)	0.4171 (2)	0.3226 (2)	0.0450 (4)
C(5)	0.6548 (2)	0.3710 (2)	0.1584 (2)	0.0471 (4)
C(6)	0.7126 (2)	0.2481 (2)	0.0935 (2)	0.0468 (4)
C(7)	0.6104 (2)	0.5454 (2)	0.3925 (2)	0.0469 (5)
C(8)	0.5412 (2)	0.6349 (2)	0.3152 (2)	0.0542 (5)
C(9)	0.4762 (2)	0.7634 (2)	0.3867 (2)	0.0526 (5)
C(10)	0.4400 (2)	0.9110 (2)	0.6243 (2)	0.0519 (5)
C(11)	0.4846 (2)	0.9127 (2)	0.7981 (2)	0.0586 (5)
C(12)	0.9212 (2)	0.1682 (2)	0.6191 (2)	0.0635 (6)
C(13)	0.8307 (2)	−0.0011 (2)	−0.0299 (2)	0.0451 (4)
C(14)	0.9001 (2)	−0.1374 (1)	−0.0652 (2)	0.0440 (4)
C(15)	0.8992 (2)	−0.2079 (2)	−0.2113 (2)	0.0435 (4)
C(16)	0.9717 (2)	−0.3443 (2)	−0.2479 (2)	0.0484 (5)
C(17)	1.0555 (2)	−0.4029 (2)	−0.1053 (2)	0.0492 (5)
C(18)	1.1279 (2)	−0.5374 (2)	−0.1583 (2)	0.0551 (5)
C(19)	1.2220 (2)	−0.6099 (2)	−0.0640 (2)	0.0522 (5)
C(20)	1.2869 (2)	−0.7440 (2)	−0.1314 (3)	0.0650 (6)
C(21)	0.8271 (2)	−0.1563 (2)	−0.3576 (2)	0.0550 (5)
C(22)	1.2703 (2)	−0.5676 (2)	0.1145 (3)	0.0688 (6)
H(3)	0.7656	0.3631	0.5345	0.0559*
H(5)	0.6013	0.4253	0.0888	0.0573*
H(6)	0.6979	0.2190	−0.0197	0.0564*
H(7)	0.6199	0.5666	0.5034	0.0570*
H(8)	0.5332	0.6146	0.2041	0.0663*
H(10a)	0.3431	0.9310	0.5828	0.0626*
H(10b)	0.4719	0.9688	0.6110	0.0626*
H(11a)	0.5811	0.8947	0.8396	0.0709*
H(11b)	0.4458	0.9926	0.8564	0.0709*
H(11c)	0.4552	0.8520	0.8101	0.0709*
H(12a)	0.8395	0.1961	0.6453	0.0768*
H(12b)	0.9634	0.2344	0.6582	0.0768*
H(12c)	0.9821	0.1016	0.6673	0.0768*
H(13a)	0.8674	0.0413	−0.0646	0.0552*
H(13b)	0.7356	0.0120	−0.0850	0.0552*
H(14)	0.9476	−0.1754	0.0228	0.0537*
H(16a)	1.0320	−0.3556	−0.3046	0.0589*
H(16b)	0.9049	−0.3883	−0.3161	0.0589*
H(17a)	1.1213	−0.3589	−0.0343	0.0600*
H(17b)	0.9964	−0.3977	−0.0515	0.0600*
H(18)	1.1032	−0.5740	−0.2708	0.0672*
H(20a)	1.3829	−0.7579	−0.0969	0.0783*
H(20b)	1.2644	−0.7958	−0.0944	0.0783*
H(20c)	1.2538	−0.7627	−0.2460	0.0783*
H(21a)	0.7697	−0.0755	−0.3305	0.0674*
H(21b)	0.7735	−0.2090	−0.4393	0.0674*
H(21c)	0.8923	−0.1519	−0.3960	0.0674*
H(22a)	1.3641	−0.5717	0.1494	0.0831*
H(22b)	1.2196	−0.4848	0.1468	0.0831*
H(22c)	1.2566	−0.6202	0.1596	0.0831*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O(1)	0.0584 (7)	0.0353 (7)	0.0354 (7)	−0.0012 (5)	0.0150 (5)	0.0062 (5)
O(2)	0.0727 (8)	0.0392 (7)	0.0380 (7)	0.0005 (6)	0.0147 (6)	0.0116 (6)
O(3)	0.116 (1)	0.0439 (8)	0.0431 (8)	0.0140 (8)	0.0183 (8)	0.0135 (6)
O(4)	0.0693 (8)	0.0377 (7)	0.0407 (7)	0.0002 (6)	0.0200 (6)	0.0087 (6)
C(1)	0.0485 (8)	0.0354 (9)	0.0401 (9)	−0.0036 (7)	0.0154 (7)	0.0076 (7)
C(2)	0.0497 (8)	0.0407 (9)	0.0399 (9)	−0.0051 (7)	0.0124 (7)	0.0127 (7)
C(3)	0.0525 (9)	0.0426 (9)	0.0340 (8)	−0.0057 (7)	0.0131 (7)	0.0066 (7)
C(4)	0.0477 (8)	0.0408 (9)	0.0388 (9)	−0.0046 (7)	0.0133 (7)	0.0076 (7)
C(5)	0.0537 (9)	0.0382 (10)	0.0386 (9)	0.0004 (7)	0.0122 (7)	0.0118 (7)
C(6)	0.0541 (9)	0.0411 (9)	0.0368 (8)	−0.0053 (7)	0.0118 (7)	0.0094 (7)
C(7)	0.0517 (9)	0.042 (1)	0.0376 (8)	−0.0048 (8)	0.0132 (7)	0.0061 (7)
C(8)	0.073 (1)	0.041 (1)	0.0352 (8)	−0.0018 (9)	0.0187 (8)	0.0047 (8)
C(9)	0.0633 (10)	0.043 (1)	0.0397 (9)	−0.0036 (8)	0.0138 (7)	0.0089 (8)
C(10)	0.067 (1)	0.0340 (9)	0.0413 (9)	−0.0007 (7)	0.0192 (8)	0.0030 (7)
C(11)	0.072 (1)	0.051 (1)	0.0420 (10)	−0.0076 (9)	0.0202 (8)	0.0040 (8)
C(12)	0.084 (1)	0.051 (1)	0.0372 (10)	−0.0011 (9)	0.0111 (8)	0.0150 (8)
C(13)	0.0524 (8)	0.0381 (9)	0.0369 (8)	−0.0066 (7)	0.0137 (7)	0.0052 (7)
C(14)	0.0502 (8)	0.0379 (10)	0.0385 (9)	−0.0045 (7)	0.0147 (7)	0.0086 (7)
C(15)	0.0459 (8)	0.0387 (9)	0.0428 (9)	−0.0060 (6)	0.0143 (7)	0.0101 (7)
C(16)	0.0572 (9)	0.0432 (10)	0.0417 (9)	−0.0081 (8)	0.0186 (7)	0.0075 (8)
C(17)	0.0610 (10)	0.0379 (9)	0.0455 (9)	−0.0039 (8)	0.0221 (8)	0.0084 (8)
C(18)	0.071 (1)	0.044 (1)	0.0490 (10)	−0.0041 (9)	0.0245 (8)	0.0128 (9)
C(19)	0.0563 (9)	0.047 (1)	0.056 (1)	−0.0064 (8)	0.0230 (8)	0.0153 (8)
C(20)	0.077 (1)	0.048 (1)	0.066 (1)	0.0023 (9)	0.029 (1)	0.0195 (10)
C(21)	0.0637 (10)	0.050 (1)	0.0379 (9)	−0.0020 (8)	0.0141 (7)	0.0097 (8)
C(22)	0.066 (1)	0.065 (1)	0.057 (1)	−0.0044 (9)	0.0103 (9)	0.016 (1)

Geometric parameters (Å, º) top

O(1)—C(1)	1.357 (2)	C(12)—H(12b)	0.953
O(1)—C(13)	1.432 (2)	C(12)—H(12c)	0.953
O(2)—C(2)	1.362 (2)	C(13)—C(14)	1.499 (2)
O(2)—C(12)	1.431 (2)	C(13)—H(13a)	0.950
O(3)—C(9)	1.207 (2)	C(13)—H(13b)	0.952
O(4)—C(9)	1.330 (2)	C(14)—C(15)	1.323 (3)
O(4)—C(10)	1.449 (2)	C(14)—H(14)	0.950
C(1)—C(2)	1.417 (2)	C(15)—C(16)	1.508 (2)
C(1)—C(6)	1.397 (2)	C(15)—C(21)	1.500 (2)
C(2)—C(3)	1.375 (2)	C(16)—C(17)	1.525 (2)
C(3)—C(4)	1.409 (2)	C(16)—H(16a)	0.955
C(3)—H(3)	0.951	C(16)—H(16b)	0.950
C(4)—C(5)	1.389 (2)	C(17)—C(18)	1.507 (3)
C(4)—C(7)	1.455 (3)	C(17)—H(17a)	0.948
C(5)—C(6)	1.384 (3)	C(17)—H(17b)	0.947
C(5)—H(5)	0.951	C(18)—C(19)	1.325 (3)
C(6)—H(6)	0.952	C(18)—H(18)	0.950
C(7)—C(8)	1.326 (3)	C(19)—C(20)	1.508 (3)
C(7)—H(7)	0.945	C(19)—C(22)	1.486 (3)
C(8)—C(9)	1.469 (3)	C(20)—H(20a)	0.949
C(8)—H(8)	0.952	C(20)—H(20b)	0.948
C(10)—C(11)	1.492 (2)	C(20)—H(20c)	0.952
C(10)—H(10a)	0.952	C(21)—H(21a)	0.951
C(10)—H(10b)	0.946	C(21)—H(21b)	0.950
C(11)—H(11a)	0.949	C(21)—H(21c)	0.950
C(11)—H(11b)	0.951	C(22)—H(22a)	0.946
C(11)—H(11c)	0.952	C(22)—H(22b)	0.947
C(12)—H(12a)	0.943	C(22)—H(22c)	0.952

O(1)···C(12)ⁱ	3.558 (2)	C(1)···C(15)ⁱⁱⁱ	3.552 (2)
O(2)···O(2)ⁱ	3.255 (2)	C(1)···C(11)^iv	3.582 (3)
O(2)···C(12)ⁱ	3.332 (2)	C(11)···C(11)^v	3.547 (4)
O(3)···C(6)ⁱⁱ	3.381 (2)	C(13)···C(13)ⁱⁱⁱ	3.578 (3)
O(3)···C(13)ⁱⁱ	3.448 (2)	C(13)···C(14)ⁱⁱⁱ	3.595 (2)

C(1)—O(1)—C(13)	116.3 (1)	O(1)—C(13)—C(14)	108.5 (1)
C(2)—O(2)—C(12)	116.8 (1)	O(1)—C(13)—H(13a)	109.9
C(9)—O(4)—C(10)	116.6 (1)	O(1)—C(13)—H(13b)	109.7
O(1)—C(1)—C(2)	116.7 (1)	C(14)—C(13)—H(13a)	109.7
O(1)—C(1)—C(6)	124.7 (2)	C(14)—C(13)—H(13b)	109.6
C(2)—C(1)—C(6)	118.6 (2)	H(13a)—C(13)—H(13b)	109.4
O(2)—C(2)—C(1)	114.5 (1)	C(13)—C(14)—C(15)	124.0 (1)
O(2)—C(2)—C(3)	125.7 (1)	C(13)—C(14)—H(14)	118.0
C(1)—C(2)—C(3)	119.8 (1)	C(15)—C(14)—H(14)	118.0
C(2)—C(3)—C(4)	121.9 (1)	C(14)—C(15)—C(16)	124.5 (1)
C(2)—C(3)—H(3)	119.1	C(14)—C(15)—C(21)	121.9 (2)
C(4)—C(3)—H(3)	119.0	C(16)—C(15)—C(21)	113.6 (1)
C(3)—C(4)—C(5)	117.4 (2)	C(15)—C(16)—C(17)	117.3 (1)
C(3)—C(4)—C(7)	120.0 (1)	C(15)—C(16)—H(16a)	107.6
C(5)—C(4)—C(7)	122.5 (2)	C(15)—C(16)—H(16b)	107.8
C(4)—C(5)—C(6)	121.8 (1)	C(17)—C(16)—H(16a)	107.3
C(4)—C(5)—H(5)	119.1	C(17)—C(16)—H(16b)	107.6
C(6)—C(5)—H(5)	119.1	H(16a)—C(16)—H(16b)	109.1
C(1)—C(6)—C(5)	120.5 (2)	C(16)—C(17)—C(18)	111.7 (1)
C(1)—C(6)—H(6)	119.7	C(16)—C(17)—H(17a)	108.9
C(5)—C(6)—H(6)	119.9	C(16)—C(17)—H(17b)	108.8
C(4)—C(7)—C(8)	126.1 (2)	C(18)—C(17)—H(17a)	108.8
C(4)—C(7)—H(7)	116.8	C(18)—C(17)—H(17b)	108.8
C(8)—C(7)—H(7)	117.1	H(17a)—C(17)—H(17b)	109.9
C(7)—C(8)—C(9)	125.4 (2)	C(17)—C(18)—C(19)	126.7 (2)
C(7)—C(8)—H(8)	117.4	C(17)—C(18)—H(18)	116.5
C(9)—C(8)—H(8)	117.1	C(19)—C(18)—H(18)	116.8
O(3)—C(9)—O(4)	122.5 (2)	C(18)—C(19)—C(20)	121.9 (2)
O(3)—C(9)—C(8)	124.2 (2)	C(18)—C(19)—C(22)	123.4 (2)
O(4)—C(9)—C(8)	113.2 (1)	C(20)—C(19)—C(22)	114.7 (2)
O(4)—C(10)—C(11)	106.0 (1)	C(19)—C(20)—H(20a)	109.5
O(4)—C(10)—H(10a)	110.3	C(19)—C(20)—H(20b)	109.4
O(4)—C(10)—H(10b)	110.7	C(19)—C(20)—H(20c)	109.5
C(11)—C(10)—H(10a)	109.9	H(20a)—C(20)—H(20b)	109.7
C(11)—C(10)—H(10b)	110.2	H(20a)—C(20)—H(20c)	109.4
H(10a)—C(10)—H(10b)	109.7	H(20b)—C(20)—H(20c)	109.4
C(10)—C(11)—H(11a)	109.6	C(15)—C(21)—H(21a)	109.5
C(10)—C(11)—H(11b)	109.6	C(15)—C(21)—H(21b)	109.4
C(10)—C(11)—H(11c)	109.7	C(15)—C(21)—H(21c)	109.6
H(11a)—C(11)—H(11b)	109.4	H(21a)—C(21)—H(21b)	109.4
H(11a)—C(11)—H(11c)	109.3	H(21a)—C(21)—H(21c)	109.5
H(11b)—C(11)—H(11c)	109.2	H(21b)—C(21)—H(21c)	109.5
O(2)—C(12)—H(12a)	109.8	C(19)—C(22)—H(22a)	109.5
O(2)—C(12)—H(12b)	109.2	C(19)—C(22)—H(22b)	109.1
O(2)—C(12)—H(12c)	109.2	C(19)—C(22)—H(22c)	109.0
H(12a)—C(12)—H(12b)	109.8	H(22a)—C(22)—H(22b)	110.0
H(12a)—C(12)—H(12c)	109.8	H(22a)—C(22)—H(22c)	109.6
H(12b)—C(12)—H(12c)	109.0	H(22b)—C(22)—H(22c)	109.6

O(1)—C(1)—C(2)—O(2)	0.7 (2)	C(3)—C(2)—C(1)—C(6)	0.7 (2)
O(1)—C(1)—C(2)—C(3)	−178.2 (1)	C(3)—C(4)—C(5)—C(6)	0.7 (3)
O(1)—C(1)—C(6)—C(5)	179.2 (1)	C(3)—C(4)—C(7)—C(8)	174.6 (2)
O(1)—C(13)—C(14)—C(15)	180.0 (1)	C(4)—C(7)—C(8)—C(9)	178.4 (2)
O(2)—C(2)—C(1)—C(6)	179.6 (1)	C(5)—C(4)—C(7)—C(8)	−5.9 (3)
O(2)—C(2)—C(3)—C(4)	−179.9 (2)	C(6)—C(1)—O(1)—C(13)	0.6 (2)
O(3)—C(9)—O(4)—C(10)	−1.1 (3)	C(6)—C(5)—C(4)—C(7)	−178.9 (1)
O(3)—C(9)—C(8)—C(7)	−176.8 (2)	C(8)—C(9)—O(4)—C(10)	178.9 (1)
O(4)—C(9)—C(8)—C(7)	3.2 (3)	C(9)—O(4)—C(10)—C(11)	−177.5 (2)
C(1)—O(1)—C(13)—C(14)	−178.2 (1)	C(13)—C(14)—C(15)—C(16)	178.3 (1)
C(1)—C(2)—O(2)—C(12)	177.6 (2)	C(13)—C(14)—C(15)—C(21)	−0.1 (3)
C(1)—C(2)—C(3)—C(4)	−1.2 (3)	C(14)—C(15)—C(16)—C(17)	−2.3 (2)
C(1)—C(6)—C(5)—C(4)	−1.2 (3)	C(15)—C(16)—C(17)—C(18)	−177.1 (1)
C(2)—C(1)—O(1)—C(13)	179.4 (1)	C(16)—C(17)—C(18)—C(19)	170.5 (2)
C(2)—C(1)—C(6)—C(5)	0.5 (3)	C(17)—C(16)—C(15)—C(21)	176.1 (1)
C(2)—C(3)—C(4)—C(5)	0.5 (3)	C(17)—C(18)—C(19)—C(20)	179.6 (2)
C(2)—C(3)—C(4)—C(7)	−179.9 (1)	C(17)—C(18)—C(19)—C(22)	0.8 (3)
C(3)—C(2)—O(2)—C(12)	−3.6 (3)

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+2, −y, −z; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₂H₃₀O₄
M_r	358.48
Crystal system, space group	Triclinic, P1
Temperature (K)	193
a, b, c (Å)	11.094 (1), 11.943 (1), 9.3399 (9)
α, β, γ (°)	110.864 (5), 113.510 (5), 68.358 (4)
V (Å³)	1022.5 (2)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.60 × 0.58 × 0.30

Data collection
Diffractometer	Rigaku R-AXIS-RAPID Imaging Plate diffractometer
Absorption correction	Multi-scan (Higashi, 1995)
T_min, T_max	0.587, 0.828
No. of measured, independent and observed [F² > 2.0σ(F²)] reflections	5896, 3429, 3094
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.121, 1.65
No. of reflections	3429
No. of parameters	326
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.28

Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, TEXSAN (Molecular Structure Corporation, 1999), SHELXS97 (Sheldrick, 1997), TEXSAN.

Selected torsion angles (º) top

O(1)—C(13)—C(14)—C(15)	180.0 (1)	C(6)—C(1)—O(1)—C(13)	0.6 (2)
O(3)—C(9)—O(4)—C(10)	−1.1 (3)	C(8)—C(9)—O(4)—C(10)	178.9 (1)
O(3)—C(9)—C(8)—C(7)	−176.8 (2)	C(9)—O(4)—C(10)—C(11)	−177.5 (2)
O(4)—C(9)—C(8)—C(7)	3.2 (3)	C(13)—C(14)—C(15)—C(16)	178.3 (1)
C(1)—O(1)—C(13)—C(14)	−178.2 (1)	C(13)—C(14)—C(15)—C(21)	−0.1 (3)
C(1)—C(2)—O(2)—C(12)	177.6 (2)	C(14)—C(15)—C(16)—C(17)	−2.3 (2)
C(2)—C(1)—O(1)—C(13)	179.4 (1)	C(15)—C(16)—C(17)—C(18)	−177.1 (1)
C(3)—C(2)—O(2)—C(12)	−3.6 (3)	C(16)—C(17)—C(18)—C(19)	170.5 (2)
C(3)—C(4)—C(7)—C(8)	174.6 (2)	C(17)—C(16)—C(15)—C(21)	176.1 (1)
C(4)—C(7)—C(8)—C(9)	178.4 (2)	C(17)—C(18)—C(19)—C(20)	179.6 (2)
C(5)—C(4)—C(7)—C(8)	−5.9 (3)	C(17)—C(18)—C(19)—C(22)	0.8 (3)

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