5,7-Bis(benz­yloxy)-2-[4-(benz­yloxy)phen­yl]-4H-chromen-4-one

Ren, X.-H.; Xie, W.-J.; Ma, C.; Wang, J.-J.; Cheng, M.-S.

doi:10.1107/S1600536809051678

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o63

doi:10.1107/S1600536809051678

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5,7-Bis(benzyloxy)-2-[4-(benzyloxy)phenyl]-4H-chromen-4-one

Xu-Hong Ren,^a Wei-Jia Xie,^b Chao Ma,^a Jing-Jing Wang ^a and Mao-Sheng Cheng ^a ^*

^aSchool of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Mail Box 40, 103 Wenhua Road, Shenhe District, Shenyang 110016, People's Republic of China, and ^bSchool of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan
^*Correspondence e-mail: mscheng@syphu.edu.cn

(Received 22 November 2009; accepted 1 December 2009; online 4 December 2009)

In the title compound, C₃₆H₂₈O₅, the terminal benzene rings are twisted at dihedral angles of 6.75 (12), 70.86 (14) and 82.02 (12)° with the respect to the central plana r[maximum deviation = 0.070 (3) Å] chromen-4-one ring system. In the crystal structure, π–π stacking is observed between parallel benzene rings of adjacent molecules [centroid–centroid distance = 3.7459 (16) Å].

Related literature

For general background to the biological effects of flavones, see: Formica & Regelson (1995 ); Medina et al. (1998 ); Cotelle et al. (1992 ). For a related structure, see: Waller et al. (2003 ).

Experimental

Crystal data

C₃₆H₂₈O₅
M_r = 540.58
Triclinic, $[P \overline 1]$
a = 7.3176 (12) Å
b = 12.818 (2) Å
c = 14.933 (2) Å
α = 82.542 (3)°
β = 83.861 (3)°
γ = 85.600 (3)°
V = 1378.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.35 × 0.22 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
7198 measured reflections
4786 independent reflections
2505 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.140
S = 0.99
4786 reflections
370 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051678/xu2692sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051678/xu2692Isup2.hkl

checkCIF report

Comment top

Flavones are among the most ubiquitous groups of polyphenolic compounds in foods of plant origin. As integral constituents of the diet, they may exert a wide range of beneficial effects on human health, including protection against cardiovascular disease, certain forms of cancer (Formica & Regelson 1995) and modulatory activities at GABA-A receptors (Medina et al., 1998). Flavones likely produce such biological effects through their free radical-scavenging antioxidative activities and metal ion-chelating a bilities (Cotelle et al.1992). Some flavones are more potent than ascorbic acid and tocopherols in scavenging reactive oxygen species. The title compound was crystallized as part of an ongoing structure-activity study to determine the properties of those compounds that confer this activity in order to aid the design of more active compounds.

The molecular is shown in shown in Fig. 1, the bond lengths and angles are within normal ranges. The bond length of the carbonyl group C7=O2 of 1.228 Å is somewhat longer than typical carbonyl bond. This may be due to the fact that atom O2 participate in intermolecular Van der Waals forces. And the bond lengths of C1—O3, C3—O4 and C27—O5 are 1.353 Å, 1.369 Å and 1.375 Å, respectively. In the crystal structure π-π stacking is observed between parallel C24-benzene and C24ⁱ-benzene rings of adjacent molecules [centroids distance 3.7459 (16) Å; symmetry code: (i) 2-x, 1-y, 2-z].

Related literature top

For general background to the biological effects of flavones, see: Formica & Regelson (1995); Medina et al. (1998); Cotelle et al. (1992). For a related structure, see: Waller et al. (2003).

Experimental top

E-3-(4-Phenoxyphenyl)-1-(2,4-bisphenoxy-6-hydroxyphenyl) propenone (2 g, 3.40 mmol) was dissolved in DMSO (40 ml). I₂ (96 mg, 0.377 mmol) was added to the solution. The reaction mixture was heated at 400 K for 2 h under N₂, then coolded to room temperature. The mixture was pured to 200 ml 1M HCl solution. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with NaHCO₃ solution, watre and brine, and dried by MgSO₄ and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (elutant: hexanesethyl /acetate, 4:1). Single crystals suitable for X-ray diffraction were obtained by solw evaporation of a dilute solution of the title compound in methanol/dichloromethane (1:5).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.

5,7-Bis(benzyloxy)-2-[4-(benzyloxy)phenyl]-4H-chromen-4-one top

Crystal data top

C₃₆H₂₈O₅	Z = 2
M_r = 540.58	F(000) = 568
Triclinic, P1	D_x = 1.303 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3176 (12) Å	Cell parameters from 1081 reflections
b = 12.818 (2) Å	θ = 2.2–21.3°
c = 14.933 (2) Å	µ = 0.09 mm⁻¹
α = 82.542 (3)°	T = 293 K
β = 83.861 (3)°	Platelet, colorless
γ = 85.600 (3)°	0.35 × 0.22 × 0.08 mm
V = 1378.0 (4) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2505 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 25.0°, θ_min = 1.4°
ϕ and ω scans	h = −8→7
7198 measured reflections	k = −15→14
4786 independent reflections	l = −17→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0563P)² + 0.0156P] where P = (F_o² + 2F_c²)/3
4786 reflections	(Δ/σ)_max < 0.001
370 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₃₆H₂₈O₅	γ = 85.600 (3)°
M_r = 540.58	V = 1378.0 (4) Å³
Triclinic, P1	Z = 2
a = 7.3176 (12) Å	Mo Kα radiation
b = 12.818 (2) Å	µ = 0.09 mm⁻¹
c = 14.933 (2) Å	T = 293 K
α = 82.542 (3)°	0.35 × 0.22 × 0.08 mm
β = 83.861 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2505 reflections with I > 2σ(I)
7198 measured reflections	R_int = 0.021
4786 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 0.99	Δρ_max = 0.13 e Å⁻³
4786 reflections	Δρ_min = −0.14 e Å⁻³
370 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.4399 (4)	0.5313 (2)	0.65974 (17)	0.0615 (7)
C2	0.3089 (3)	0.6140 (2)	0.65568 (17)	0.0637 (7)
H2	0.2078	0.6118	0.6233	0.076*
C3	0.3274 (4)	0.7009 (2)	0.69977 (19)	0.0650 (8)
C4	0.4748 (3)	0.7066 (2)	0.74818 (18)	0.0666 (8)
H4	0.4882	0.7653	0.7770	0.080*
C5	0.6029 (3)	0.6210 (2)	0.75215 (17)	0.0569 (7)
C6	0.5971 (3)	0.5329 (2)	0.70836 (17)	0.0578 (7)
C7	0.7481 (4)	0.4513 (2)	0.71387 (19)	0.0646 (7)
C8	0.8810 (4)	0.4680 (2)	0.77456 (18)	0.0649 (7)
H8	0.9751	0.4161	0.7845	0.078*
C9	0.8767 (3)	0.5535 (2)	0.81716 (17)	0.0567 (7)
C10	0.2776 (4)	0.4369 (2)	0.56895 (18)	0.0717 (8)
H10A	0.2759	0.4939	0.5195	0.086*
H10B	0.1631	0.4428	0.6078	0.086*
C11	0.2968 (4)	0.3326 (2)	0.53217 (17)	0.0658 (7)
C12	0.4499 (4)	0.2647 (2)	0.53946 (18)	0.0764 (8)
H12	0.5462	0.2817	0.5697	0.092*
C13	0.4618 (5)	0.1707 (3)	0.5019 (2)	0.0919 (10)
H13	0.5659	0.1248	0.5073	0.110*
C14	0.3212 (6)	0.1451 (3)	0.4571 (2)	0.1017 (11)
H14	0.3297	0.0821	0.4316	0.122*
C15	0.1680 (6)	0.2126 (3)	0.4499 (2)	0.1067 (12)
H15	0.0720	0.1956	0.4194	0.128*
C16	0.1558 (4)	0.3050 (3)	0.4874 (2)	0.0909 (10)
H16	0.0505	0.3500	0.4826	0.109*
C17	0.1970 (4)	0.8678 (2)	0.7378 (2)	0.0819 (9)
H17A	0.3049	0.9057	0.7139	0.098*
H17B	0.2055	0.8452	0.8018	0.098*
C18	0.0252 (4)	0.9384 (2)	0.7251 (2)	0.0664 (8)
C19	0.0278 (4)	1.0262 (2)	0.6621 (2)	0.0863 (10)
H19	0.1349	1.0402	0.6244	0.104*
C20	−0.1269 (6)	1.0941 (3)	0.6540 (2)	0.1007 (11)
H20	−0.1230	1.1539	0.6115	0.121*
C21	−0.2839 (5)	1.0739 (3)	0.7077 (2)	0.0919 (11)
H21	−0.3878	1.1199	0.7021	0.110*
C22	−0.2905 (4)	0.9869 (3)	0.7696 (2)	0.0881 (10)
H22	−0.3990	0.9730	0.8063	0.106*
C23	−0.1360 (4)	0.9187 (2)	0.7783 (2)	0.0807 (9)
H23	−0.1414	0.8588	0.8207	0.097*
C24	1.0066 (3)	0.5790 (2)	0.87816 (17)	0.0545 (7)
C25	1.1804 (3)	0.5272 (2)	0.88121 (17)	0.0605 (7)
H25	1.2117	0.4714	0.8473	0.073*
C26	1.3063 (4)	0.5567 (2)	0.93301 (17)	0.0638 (7)
H26	1.4220	0.5213	0.9335	0.077*
C27	1.2622 (4)	0.6387 (2)	0.98449 (17)	0.0610 (7)
C28	1.0861 (4)	0.6875 (2)	0.98691 (18)	0.0695 (8)
H28	1.0524	0.7401	1.0240	0.083*
C29	0.9617 (4)	0.6573 (2)	0.93393 (18)	0.0656 (7)
H29	0.8440	0.6905	0.9356	0.079*
C30	1.3635 (4)	0.7560 (2)	1.0795 (2)	0.0817 (9)
H30A	1.2865	0.7359	1.1351	0.098*
H30B	1.2981	0.8127	1.0439	0.098*
C31	1.5407 (4)	0.7924 (2)	1.1012 (2)	0.0676 (8)
C32	1.6274 (5)	0.8700 (3)	1.0444 (2)	0.0886 (10)
H32	1.5782	0.8973	0.9907	0.106*
C33	1.7863 (6)	0.9085 (3)	1.0654 (3)	0.1061 (12)
H33	1.8439	0.9613	1.0263	0.127*
C34	1.8587 (5)	0.8682 (4)	1.1447 (4)	0.1072 (13)
H34	1.9651	0.8941	1.1598	0.129*
C35	1.7749 (5)	0.7903 (3)	1.2013 (3)	0.0928 (10)
H35	1.8257	0.7624	1.2544	0.111*
C36	1.6151 (4)	0.7525 (2)	1.1804 (2)	0.0796 (9)
H36	1.5576	0.7000	1.2198	0.096*
O1	0.7420 (2)	0.63213 (13)	0.80484 (12)	0.0647 (5)
O2	0.7642 (3)	0.37370 (17)	0.67264 (15)	0.0968 (7)
O3	0.4297 (2)	0.44352 (14)	0.61951 (12)	0.0745 (6)
O4	0.1888 (2)	0.77832 (14)	0.69079 (13)	0.0772 (6)
O5	1.4013 (2)	0.66769 (14)	1.02937 (13)	0.0767 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0644 (18)	0.0570 (18)	0.0630 (18)	0.0071 (15)	−0.0114 (15)	−0.0095 (14)
C2	0.0628 (18)	0.0577 (18)	0.0724 (19)	0.0051 (15)	−0.0217 (14)	−0.0080 (14)
C3	0.0576 (17)	0.0521 (17)	0.084 (2)	0.0097 (15)	−0.0182 (15)	−0.0008 (15)
C4	0.0617 (18)	0.0525 (17)	0.087 (2)	0.0054 (15)	−0.0198 (16)	−0.0087 (14)
C5	0.0465 (16)	0.0557 (17)	0.0681 (18)	−0.0016 (14)	−0.0129 (14)	−0.0010 (14)
C6	0.0569 (17)	0.0540 (17)	0.0605 (17)	0.0012 (14)	−0.0054 (14)	−0.0028 (13)
C7	0.0580 (18)	0.0626 (19)	0.072 (2)	0.0110 (15)	−0.0102 (15)	−0.0101 (15)
C8	0.0578 (17)	0.0625 (19)	0.0726 (19)	0.0160 (14)	−0.0137 (15)	−0.0076 (15)
C9	0.0478 (16)	0.0530 (17)	0.0656 (18)	0.0075 (14)	−0.0063 (14)	0.0016 (14)
C10	0.0716 (19)	0.076 (2)	0.0697 (19)	0.0089 (16)	−0.0236 (16)	−0.0123 (15)
C11	0.078 (2)	0.0660 (19)	0.0535 (17)	0.0057 (17)	−0.0148 (15)	−0.0061 (14)
C12	0.091 (2)	0.071 (2)	0.0679 (19)	0.0125 (18)	−0.0205 (16)	−0.0140 (16)
C13	0.120 (3)	0.081 (2)	0.075 (2)	0.018 (2)	−0.014 (2)	−0.0175 (18)
C14	0.160 (4)	0.080 (2)	0.069 (2)	−0.002 (3)	−0.021 (2)	−0.0232 (18)
C15	0.140 (3)	0.099 (3)	0.092 (3)	−0.011 (3)	−0.043 (2)	−0.024 (2)
C16	0.098 (3)	0.091 (3)	0.090 (2)	0.010 (2)	−0.041 (2)	−0.020 (2)
C17	0.078 (2)	0.066 (2)	0.109 (2)	0.0175 (16)	−0.0397 (18)	−0.0230 (18)
C18	0.068 (2)	0.0559 (18)	0.079 (2)	0.0085 (16)	−0.0256 (17)	−0.0155 (15)
C19	0.083 (2)	0.083 (2)	0.089 (2)	0.0090 (19)	−0.0125 (18)	−0.0008 (19)
C20	0.116 (3)	0.077 (2)	0.105 (3)	0.024 (2)	−0.028 (2)	0.005 (2)
C21	0.099 (3)	0.085 (3)	0.093 (3)	0.038 (2)	−0.032 (2)	−0.026 (2)
C22	0.072 (2)	0.105 (3)	0.088 (2)	0.014 (2)	−0.0149 (18)	−0.023 (2)
C23	0.087 (2)	0.069 (2)	0.086 (2)	0.0047 (19)	−0.0244 (19)	−0.0023 (16)
C24	0.0492 (16)	0.0534 (16)	0.0576 (17)	0.0075 (13)	−0.0050 (13)	−0.0003 (13)
C25	0.0590 (17)	0.0578 (17)	0.0649 (18)	0.0097 (14)	−0.0118 (14)	−0.0120 (13)
C26	0.0600 (17)	0.0620 (18)	0.0685 (19)	0.0157 (15)	−0.0137 (15)	−0.0101 (15)
C27	0.0597 (18)	0.0608 (18)	0.0623 (18)	0.0112 (15)	−0.0166 (14)	−0.0071 (14)
C28	0.0677 (19)	0.0695 (19)	0.072 (2)	0.0157 (16)	−0.0138 (16)	−0.0195 (15)
C29	0.0576 (17)	0.0646 (19)	0.0727 (19)	0.0156 (14)	−0.0132 (15)	−0.0072 (15)
C30	0.079 (2)	0.073 (2)	0.097 (2)	0.0116 (17)	−0.0174 (18)	−0.0276 (18)
C31	0.0644 (19)	0.0577 (19)	0.082 (2)	0.0105 (16)	−0.0081 (17)	−0.0223 (16)
C32	0.091 (3)	0.079 (2)	0.094 (2)	0.005 (2)	−0.005 (2)	−0.011 (2)
C33	0.091 (3)	0.081 (3)	0.144 (4)	−0.015 (2)	0.018 (3)	−0.028 (3)
C34	0.076 (3)	0.107 (3)	0.153 (4)	0.000 (2)	−0.008 (3)	−0.077 (3)
C35	0.085 (3)	0.101 (3)	0.100 (3)	0.016 (2)	−0.023 (2)	−0.038 (2)
C36	0.081 (2)	0.072 (2)	0.087 (2)	0.0076 (18)	−0.0140 (18)	−0.0186 (17)
O1	0.0524 (10)	0.0543 (11)	0.0878 (13)	0.0077 (9)	−0.0182 (10)	−0.0081 (9)
O2	0.0871 (15)	0.0890 (16)	0.1244 (18)	0.0318 (12)	−0.0368 (13)	−0.0515 (14)
O3	0.0747 (13)	0.0691 (13)	0.0845 (14)	0.0159 (10)	−0.0314 (11)	−0.0211 (11)
O4	0.0724 (13)	0.0595 (12)	0.1057 (15)	0.0187 (10)	−0.0378 (11)	−0.0223 (11)
O5	0.0711 (13)	0.0715 (13)	0.0933 (14)	0.0202 (10)	−0.0288 (11)	−0.0291 (11)

Geometric parameters (Å, º) top

C1—O3	1.352 (3)	C18—C19	1.370 (4)
C1—C2	1.374 (3)	C18—C23	1.371 (4)
C1—C6	1.427 (3)	C19—C20	1.380 (4)
C2—C3	1.388 (3)	C19—H19	0.9300
C2—H2	0.9300	C20—C21	1.351 (4)
C3—O4	1.368 (3)	C20—H20	0.9300
C3—C4	1.373 (3)	C21—C22	1.353 (4)
C4—C5	1.387 (3)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.382 (4)
C5—O1	1.378 (3)	C22—H22	0.9300
C5—C6	1.382 (3)	C23—H23	0.9300
C6—C7	1.463 (3)	C24—C29	1.384 (3)
C7—O2	1.228 (3)	C24—C25	1.392 (3)
C7—C8	1.443 (4)	C25—C26	1.368 (3)
C8—C9	1.334 (3)	C25—H25	0.9300
C8—H8	0.9300	C26—C27	1.380 (3)
C9—O1	1.363 (3)	C26—H26	0.9300
C9—C24	1.466 (3)	C27—O5	1.375 (3)
C10—O3	1.424 (3)	C27—C28	1.388 (3)
C10—C11	1.501 (4)	C28—C29	1.375 (3)
C10—H10A	0.9700	C28—H28	0.9300
C10—H10B	0.9700	C29—H29	0.9300
C11—C12	1.370 (3)	C30—O5	1.430 (3)
C11—C16	1.379 (4)	C30—C31	1.492 (4)
C12—C13	1.387 (4)	C30—H30A	0.9700
C12—H12	0.9300	C30—H30B	0.9700
C13—C14	1.368 (4)	C31—C32	1.370 (4)
C13—H13	0.9300	C31—C36	1.376 (4)
C14—C15	1.368 (4)	C32—C33	1.378 (4)
C14—H14	0.9300	C32—H32	0.9300
C15—C16	1.368 (4)	C33—C34	1.372 (5)
C15—H15	0.9300	C33—H33	0.9300
C16—H16	0.9300	C34—C35	1.360 (5)
C17—O4	1.428 (3)	C34—H34	0.9300
C17—C18	1.505 (3)	C35—C36	1.380 (4)
C17—H17A	0.9700	C35—H35	0.9300
C17—H17B	0.9700	C36—H36	0.9300

O3—C1—C2	123.3 (2)	C18—C19—H19	119.7
O3—C1—C6	115.5 (2)	C20—C19—H19	119.7
C2—C1—C6	121.2 (3)	C21—C20—C19	120.2 (3)
C1—C2—C3	120.0 (3)	C21—C20—H20	119.9
C1—C2—H2	120.0	C19—C20—H20	119.9
C3—C2—H2	120.0	C20—C21—C22	120.2 (3)
O4—C3—C4	123.8 (3)	C20—C21—H21	119.9
O4—C3—C2	114.8 (2)	C22—C21—H21	119.9
C4—C3—C2	121.5 (2)	C21—C22—C23	119.9 (3)
C3—C4—C5	117.0 (3)	C21—C22—H22	120.0
C3—C4—H4	121.5	C23—C22—H22	120.0
C5—C4—H4	121.5	C18—C23—C22	120.7 (3)
O1—C5—C6	122.0 (2)	C18—C23—H23	119.6
O1—C5—C4	112.9 (2)	C22—C23—H23	119.6
C6—C5—C4	125.1 (2)	C29—C24—C25	117.4 (2)
C5—C6—C1	115.2 (2)	C29—C24—C9	121.0 (2)
C5—C6—C7	119.2 (2)	C25—C24—C9	121.6 (2)
C1—C6—C7	125.6 (3)	C26—C25—C24	121.4 (3)
O2—C7—C8	121.1 (2)	C26—C25—H25	119.3
O2—C7—C6	124.9 (3)	C24—C25—H25	119.3
C8—C7—C6	114.0 (3)	C25—C26—C27	120.3 (2)
C9—C8—C7	123.8 (2)	C25—C26—H26	119.9
C9—C8—H8	118.1	C27—C26—H26	119.9
C7—C8—H8	118.1	O5—C27—C26	116.3 (2)
C8—C9—O1	120.5 (2)	O5—C27—C28	124.3 (3)
C8—C9—C24	128.1 (2)	C26—C27—C28	119.4 (3)
O1—C9—C24	111.4 (2)	C29—C28—C27	119.4 (3)
O3—C10—C11	108.4 (2)	C29—C28—H28	120.3
O3—C10—H10A	110.0	C27—C28—H28	120.3
C11—C10—H10A	110.0	C28—C29—C24	121.9 (2)
O3—C10—H10B	110.0	C28—C29—H29	119.0
C11—C10—H10B	110.0	C24—C29—H29	119.0
H10A—C10—H10B	108.4	O5—C30—C31	109.2 (2)
C12—C11—C16	118.6 (3)	O5—C30—H30A	109.8
C12—C11—C10	122.9 (3)	C31—C30—H30A	109.8
C16—C11—C10	118.6 (3)	O5—C30—H30B	109.8
C11—C12—C13	120.2 (3)	C31—C30—H30B	109.8
C11—C12—H12	119.9	H30A—C30—H30B	108.3
C13—C12—H12	119.9	C32—C31—C36	118.9 (3)
C14—C13—C12	120.4 (3)	C32—C31—C30	120.2 (3)
C14—C13—H13	119.8	C36—C31—C30	120.9 (3)
C12—C13—H13	119.8	C31—C32—C33	121.2 (3)
C15—C14—C13	119.5 (3)	C31—C32—H32	119.4
C15—C14—H14	120.2	C33—C32—H32	119.4
C13—C14—H14	120.2	C34—C33—C32	119.3 (4)
C14—C15—C16	120.1 (3)	C34—C33—H33	120.3
C14—C15—H15	120.0	C32—C33—H33	120.3
C16—C15—H15	120.0	C35—C34—C33	120.1 (4)
C15—C16—C11	121.2 (3)	C35—C34—H34	120.0
C15—C16—H16	119.4	C33—C34—H34	120.0
C11—C16—H16	119.4	C34—C35—C36	120.5 (4)
O4—C17—C18	108.5 (2)	C34—C35—H35	119.8
O4—C17—H17A	110.0	C36—C35—H35	119.8
C18—C17—H17A	110.0	C31—C36—C35	120.1 (3)
O4—C17—H17B	110.0	C31—C36—H36	120.0
C18—C17—H17B	110.0	C35—C36—H36	120.0
H17A—C17—H17B	108.4	C9—O1—C5	120.0 (2)
C19—C18—C23	118.2 (3)	C1—O3—C10	118.6 (2)
C19—C18—C17	120.7 (3)	C3—O4—C17	117.2 (2)
C23—C18—C17	121.0 (3)	C27—O5—C30	117.8 (2)
C18—C19—C20	120.7 (3)

Experimental details

Crystal data
Chemical formula	C₃₆H₂₈O₅
M_r	540.58
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.3176 (12), 12.818 (2), 14.933 (2)
α, β, γ (°)	82.542 (3), 83.861 (3), 85.600 (3)
V (Å³)	1378.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.22 × 0.08

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7198, 4786, 2505
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.140, 0.99
No. of reflections	4786
No. of parameters	370
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.14

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

References

Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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