1,4-Bis[(3,5-dimethoxy­phen­yl)ethyn­yl]benzene

Ono, K.; Nakagawa, K.; Tomura, M.

doi:10.1107/S160053680900155X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o346

doi:10.1107/S160053680900155X

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1,4-Bis[(3,5-dimethoxyphenyl)ethynyl]benzene

Katsuhiko Ono,^a ^* Koki Nakagawa ^a and Masaaki Tomura ^b

^aDepartment of Materials Science and Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan, and ^bInstitute for Molecular Science, Myodaiji, Okazaki 444-8585, Japan
^*Correspondence e-mail: ono.katsuhiko@nitech.ac.jp

(Received 25 December 2008; accepted 13 January 2009; online 17 January 2009)

The title compound, C₂₆H₂₂O₄, is a derivative of 1,4-bis(phenylethynyl)benzene substituted by four methoxy groups on the terminal benzene rings. The molecule is almost planar with an r.m.s. deviation of 0.266 Å. The dihedral angles between the two terminal benzene rings and the central benzene ring are 7.96 (6) and 13.32 (7)°. In the crystal structure, molecules aggregate via C—H⋯O interactions, forming molecular tapes along the a axis, which aggregate to form a herring-bone structure.

Related literature

For the crystal structure of 1,4-bis[(2,6-dimethoxyphenyl)ethynyl]benzene, see: Ono et al. (2008 ). For related sructures, including a 1,4-bis(phenylethynyl)benzene system, see: Watt et al. (2004 ); Li et al. (1998 ); Filatov & Petrukhina (2005 ).

Experimental

Crystal data

C₂₆H₂₂O₄
M_r = 398.44
Monoclinic, P 2₁ /a
a = 8.8980 (5) Å
b = 19.4610 (8) Å
c = 12.2820 (5) Å
β = 100.607 (1)°
V = 2090.46 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 (1) K
0.30 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: none
15238 measured reflections
4638 independent reflections
3914 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.140
S = 1.11
4638 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O4ⁱ	0.95	2.42	3.3511 (17)	167
C14—H14⋯O2ⁱⁱ	0.95	2.37	3.2758 (16)	160
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2001 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2003 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900155X/ci2753sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900155X/ci2753Isup2.hkl

checkCIF report

Comment top

The synthetic research of ethynylated aromatic compounds has attracted considerable attention because of interests in their molecular structures, optical properties, and molecular electronics. Among these ethynylated aromatic compounds, 1,4-bis(phenylethynyl)benzene derivatives have been extensively studied. These compounds have stiff, linear molecular structures and are used as building blocks in the applications. Recently, we found that 1,4-bis[(2,6-dimethoxyphenyl)ethynyl]benzene, (II), formed a zigzag molecular network in the crystal (Ono et al., 2008). The crystal structure is different from those of 1,4-bis(phenylethynyl)benzene derivatives (Watt et al., 2004; Li et al., 1998; Filatov & Petrukhina, 2005). With regard to this, we investigated the molecular and crystal structure of the title compound, (I), which is a regioisomer of (II). The substitution effect of four methoxy groups at the terminal benzene rings was studied.

The molecular structure of (I) is shown in Fig. 1. The molecule is almost planar with an r.m.s deviation of 0.266 Å. The dihedral angles between the terminal benzene rings and the central benzene ring are 7.96 (6)° (C1–C6) and 13.32 (7)° (C17–C22). The methoxy groups are coplanar with the attached benzene rings.

The crystal structure is characterized by a molecular tape along the a axis formed by C—H···O interactions (Table 1 and Fig. 2). The molecular tapes aggregate to form a herring-bone-type structure, as shown in Fig.3. The crystal structure of (I) is different from that of (II). The crystal structures of (I) and (II) indicate that the methoxy groups at terminal benzene rings play an important role in the crystal packing.

Related literature top

For the crystal structure of 1,4-bis[(2,6-dimethoxyphenyl)ethynyl]benzene, see: Ono et al. (2008). For related sructures, including a 1,4-bis(phenylethynyl)benzene system, see: Watt et al. (2004); Li et al. (1998); Filatov & Petrukhina (2005).

Experimental top

The title compound (I) was prepared as follows: Tetrakis(triphenylphosphine)palladium(0) [Pd(PPh₃)₄] (52 mg, 0.045 mmol) was added to a mixture of 1-ethynyl-3,5-dimethoxybenzene (0.39 g, 2.4 mmol), 1,4-diiodobenzene (0.39 g, 1.2 mmol) and copper(I) iodide (5 mg, 0.03 mmol) in dry triethylamine (7 ml) under nitrogen. The reaction mixture was stirred for 18 h at 353 K. After removal of the solvent, dichloromethane (20 ml) and aqueous disodium ethylenediaminetetraacetate (Na₂edta) solution (5%, 20 ml) were added. The organic layer was separated and washed with water (20 ml). The organic solution was dried over Na₂SO₄and concentrated. The residue was chromatographed on silica gel (CH₂Cl₂) to afford the title compound (0.23 g, 49%) as a yellow powder. Yellow crystals of the compound, suitable for X-ray analysis were grown from an ethanol solution.

Computing details top

Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear (Rigaku, 2001); data reduction: CrystalClear (Rigaku, 2001); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Partial packing diagram of (I), showing a molecular tape along the a axis.
	Fig. 3. The packing diagram of (I), showing herringbone-type network on the bc plane.

1,4-Bis[(3,5-dimethoxyphenyl)ethynyl]benzene top

Crystal data top

C₂₆H₂₂O₄	F(000) = 840
M_r = 398.44	D_x = 1.266 Mg m⁻³
Monoclinic, P2₁/a	Melting point: 431 K
Hall symbol: -P 2yab	Mo Kα radiation, λ = 0.71073 Å
a = 8.8980 (5) Å	Cell parameters from 5437 reflections
b = 19.4610 (8) Å	θ = 3.1–27.5°
c = 12.2820 (5) Å	µ = 0.09 mm⁻¹
β = 100.607 (1)°	T = 173 K
V = 2090.46 (17) Å³	Block, yellow
Z = 4	0.30 × 0.25 × 0.15 mm

Data collection top

Rigaku Mercury CCD diffractometer	3914 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.024
Graphite Monochromator monochromator	θ_max = 27.5°, θ_min = 3.1°
Detector resolution: 14.7059 pixels mm^-1	h = −11→10
ϕ and ω scans	k = −22→25
15238 measured reflections	l = −15→12
4638 independent reflections

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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.140	w = 1/[σ²(F_o²) + (0.0818P)² + 0.1522P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
4638 reflections	Δρ_max = 0.26 e Å⁻³
271 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints

Crystal data top

C₂₆H₂₂O₄	V = 2090.46 (17) Å³
M_r = 398.44	Z = 4
Monoclinic, P2₁/a	Mo Kα radiation
a = 8.8980 (5) Å	µ = 0.09 mm⁻¹
b = 19.4610 (8) Å	T = 173 K
c = 12.2820 (5) Å	0.30 × 0.25 × 0.15 mm
β = 100.607 (1)°

Data collection top

Rigaku Mercury CCD diffractometer	3914 reflections with I > 2σ(I)
15238 measured reflections	R_int = 0.024
4638 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.11	Δρ_max = 0.26 e Å⁻³
4638 reflections	Δρ_min = −0.17 e Å⁻³
271 parameters

Special details top

Experimental. IR (KBr, cm^-1): 1605, 1580, 1345, 1254, 1202, 1161, 1065, 841; ¹H NMR (CDCl₃, δ p.p.m.): 3.81 (s, 12H), 6.48 (t, J = 2.3 Hz, 2H), 6.70 (d, J = 2.3 Hz, 4H), 7.51 (s, 4H); ¹³C NMR (CDCl₃, δ p.p.m.): 55.3, 88.6, 91.3, 102.0, 109.4, 123.0, 124.3, 131.6, 160.6; MS (EI): m/z 398 (M⁺), 199.

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	0.04347 (14)	0.17522 (6)	0.71287 (10)	0.0266 (3)
C2	−0.11459 (14)	0.17481 (6)	0.67760 (11)	0.0266 (3)
H2	−0.1799	0.1980	0.7185	0.032*
C3	−0.17430 (13)	0.13932 (6)	0.58033 (11)	0.0265 (3)
C4	−0.07979 (14)	0.10623 (6)	0.51948 (11)	0.0277 (3)
H4	−0.1225	0.0824	0.4535	0.033*
C5	0.07839 (14)	0.10787 (6)	0.55512 (10)	0.0261 (3)
C6	0.14059 (14)	0.14194 (6)	0.65309 (11)	0.0283 (3)
H6	0.2480	0.1424	0.6787	0.034*
C7	0.17340 (14)	0.07642 (6)	0.48619 (11)	0.0288 (3)
C8	0.24292 (14)	0.05168 (7)	0.42138 (11)	0.0288 (3)
C9	0.32492 (14)	0.02180 (6)	0.34289 (10)	0.0262 (3)
C10	0.24597 (14)	−0.01164 (7)	0.24864 (11)	0.0286 (3)
H10	0.1377	−0.0150	0.2371	0.034*
C11	0.32439 (14)	−0.03986 (7)	0.17214 (11)	0.0303 (3)
H11	0.2695	−0.0621	0.1081	0.036*
C12	0.48372 (14)	−0.03594 (6)	0.18839 (10)	0.0273 (3)
C13	0.56275 (14)	−0.00329 (6)	0.28348 (11)	0.0297 (3)
H13	0.6712	−0.0009	0.2959	0.036*
C14	0.48439 (14)	0.02550 (7)	0.35943 (11)	0.0295 (3)
H14	0.5392	0.0479	0.4233	0.035*
C15	0.56748 (14)	−0.06453 (7)	0.10994 (11)	0.0305 (3)
C16	0.64138 (15)	−0.08764 (7)	0.04662 (11)	0.0313 (3)
C17	0.73414 (14)	−0.11338 (6)	−0.02860 (11)	0.0289 (3)
C18	0.67256 (14)	−0.15780 (7)	−0.11433 (11)	0.0309 (3)
H18	0.5689	−0.1720	−0.1231	0.037*
C19	0.76419 (14)	−0.18118 (7)	−0.18695 (11)	0.0289 (3)
C20	0.91672 (14)	−0.16179 (7)	−0.17484 (11)	0.0289 (3)
H20	0.9792	−0.1787	−0.2238	0.035*
C21	0.97568 (14)	−0.11696 (7)	−0.08931 (11)	0.0310 (3)
C22	0.88622 (14)	−0.09254 (7)	−0.01627 (11)	0.0316 (3)
H22	0.9283	−0.0619	0.0416	0.038*
C23	0.02302 (18)	0.24526 (8)	0.87014 (12)	0.0434 (4)
H23A	0.0889	0.2677	0.9328	0.065*
H23B	−0.0440	0.2122	0.8980	0.065*
H23C	−0.0392	0.2800	0.8247	0.065*
C24	−0.43253 (15)	0.17035 (8)	0.58918 (13)	0.0409 (4)
H24A	−0.5365	0.1618	0.5488	0.061*
H24B	−0.4108	0.2197	0.5890	0.061*
H24C	−0.4236	0.1543	0.6657	0.061*
C25	0.77935 (17)	−0.24753 (8)	−0.34851 (12)	0.0398 (3)
H25A	0.7151	−0.2772	−0.4025	0.060*
H25B	0.8679	−0.2737	−0.3107	0.060*
H25C	0.8146	−0.2082	−0.3868	0.060*
C26	1.22202 (17)	−0.11600 (9)	−0.14105 (15)	0.0506 (4)
H26A	1.3229	−0.0950	−0.1178	0.076*
H26B	1.1803	−0.1025	−0.2175	0.076*
H26C	1.2316	−0.1661	−0.1366	0.076*
O1	0.11541 (10)	0.21008 (5)	0.80454 (8)	0.0360 (2)
O2	−0.32622 (10)	0.13442 (5)	0.53688 (8)	0.0352 (2)
O3	0.69301 (10)	−0.22363 (5)	−0.26936 (9)	0.0396 (3)
O4	1.12292 (11)	−0.09341 (6)	−0.07075 (9)	0.0477 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0340 (6)	0.0247 (6)	0.0213 (6)	0.0006 (5)	0.0059 (5)	−0.0006 (5)
C2	0.0318 (6)	0.0241 (6)	0.0263 (7)	0.0011 (5)	0.0113 (5)	−0.0004 (5)
C3	0.0273 (6)	0.0244 (6)	0.0287 (7)	−0.0013 (4)	0.0073 (5)	0.0015 (5)
C4	0.0345 (6)	0.0257 (6)	0.0235 (6)	−0.0007 (5)	0.0068 (5)	−0.0036 (5)
C5	0.0322 (6)	0.0232 (6)	0.0249 (6)	0.0034 (5)	0.0106 (5)	0.0016 (5)
C6	0.0280 (6)	0.0281 (6)	0.0291 (7)	0.0025 (5)	0.0058 (5)	−0.0005 (5)
C7	0.0314 (6)	0.0279 (6)	0.0277 (7)	0.0016 (5)	0.0071 (5)	−0.0007 (5)
C8	0.0324 (6)	0.0280 (6)	0.0266 (7)	0.0020 (5)	0.0069 (5)	−0.0004 (5)
C9	0.0309 (6)	0.0248 (6)	0.0243 (6)	0.0033 (5)	0.0089 (5)	0.0012 (5)
C10	0.0266 (6)	0.0331 (7)	0.0265 (7)	0.0027 (5)	0.0061 (5)	−0.0005 (5)
C11	0.0340 (6)	0.0338 (7)	0.0226 (6)	0.0014 (5)	0.0042 (5)	−0.0045 (5)
C12	0.0330 (6)	0.0269 (6)	0.0238 (6)	0.0043 (5)	0.0103 (5)	0.0000 (5)
C13	0.0277 (6)	0.0333 (7)	0.0293 (7)	0.0007 (5)	0.0083 (5)	−0.0012 (5)
C14	0.0325 (6)	0.0316 (6)	0.0248 (7)	−0.0015 (5)	0.0064 (5)	−0.0051 (5)
C15	0.0346 (6)	0.0303 (7)	0.0278 (7)	0.0033 (5)	0.0086 (5)	−0.0006 (5)
C16	0.0358 (6)	0.0316 (7)	0.0278 (7)	0.0036 (5)	0.0092 (5)	−0.0007 (5)
C17	0.0344 (6)	0.0299 (6)	0.0238 (6)	0.0062 (5)	0.0089 (5)	0.0002 (5)
C18	0.0286 (6)	0.0338 (7)	0.0322 (7)	−0.0007 (5)	0.0109 (5)	−0.0034 (6)
C19	0.0317 (6)	0.0294 (6)	0.0259 (7)	−0.0011 (5)	0.0065 (5)	−0.0044 (5)
C20	0.0296 (6)	0.0330 (7)	0.0255 (7)	0.0018 (5)	0.0091 (5)	−0.0038 (5)
C21	0.0286 (6)	0.0363 (7)	0.0285 (7)	−0.0008 (5)	0.0057 (5)	−0.0029 (5)
C22	0.0356 (7)	0.0348 (7)	0.0244 (7)	0.0003 (5)	0.0057 (5)	−0.0071 (5)
C23	0.0512 (8)	0.0486 (9)	0.0291 (8)	0.0112 (7)	0.0037 (6)	−0.0135 (7)
C24	0.0286 (6)	0.0471 (9)	0.0487 (9)	0.0001 (6)	0.0112 (6)	−0.0110 (7)
C25	0.0459 (8)	0.0429 (8)	0.0324 (8)	−0.0052 (6)	0.0121 (6)	−0.0150 (6)
C26	0.0339 (7)	0.0718 (12)	0.0499 (10)	−0.0131 (7)	0.0179 (7)	−0.0190 (8)
O1	0.0364 (5)	0.0429 (6)	0.0274 (5)	0.0056 (4)	0.0023 (4)	−0.0123 (4)
O2	0.0271 (4)	0.0380 (5)	0.0403 (6)	−0.0022 (4)	0.0062 (4)	−0.0102 (4)
O3	0.0361 (5)	0.0459 (6)	0.0390 (6)	−0.0091 (4)	0.0123 (4)	−0.0198 (5)
O4	0.0302 (5)	0.0698 (7)	0.0446 (7)	−0.0122 (5)	0.0112 (4)	−0.0260 (6)

Geometric parameters (Å, º) top

C1—O1	1.3684 (15)	C17—C22	1.3940 (18)
C1—C6	1.3924 (16)	C17—C18	1.3942 (18)
C1—C2	1.3933 (17)	C18—C19	1.3911 (16)
C2—C3	1.3975 (18)	C18—H18	0.95
C2—H2	0.95	C19—O3	1.3683 (15)
C3—O2	1.3622 (15)	C19—C20	1.3900 (17)
C3—C4	1.3826 (16)	C20—C21	1.3917 (18)
C4—C5	1.3953 (17)	C20—H20	0.95
C4—H4	0.95	C21—O4	1.3670 (15)
C5—C6	1.3960 (18)	C21—C22	1.3882 (17)
C5—C7	1.4386 (16)	C22—H22	0.95
C6—H6	0.95	C23—O1	1.4274 (16)
C7—C8	1.1956 (17)	C23—H23A	0.98
C8—C9	1.4348 (16)	C23—H23B	0.98
C9—C14	1.3977 (17)	C23—H23C	0.98
C9—C10	1.3991 (18)	C24—O2	1.4213 (15)
C10—C11	1.3831 (17)	C24—H24A	0.98
C10—H10	0.95	C24—H24B	0.98
C11—C12	1.3969 (17)	C24—H24C	0.98
C11—H11	0.95	C25—O3	1.4236 (16)
C12—C13	1.3999 (18)	C25—H25A	0.98
C12—C15	1.4345 (16)	C25—H25B	0.98
C13—C14	1.3820 (17)	C25—H25C	0.98
C13—H13	0.95	C26—O4	1.4130 (17)
C14—H14	0.95	C26—H26A	0.98
C15—C16	1.1949 (18)	C26—H26B	0.98
C16—C17	1.4375 (17)	C26—H26C	0.98

O1—C1—C6	115.01 (10)	C19—C18—C17	119.46 (11)
O1—C1—C2	123.44 (11)	C19—C18—H18	120.3
C6—C1—C2	121.49 (11)	C17—C18—H18	120.3
C1—C2—C3	118.14 (11)	O3—C19—C20	123.57 (11)
C1—C2—H2	120.9	O3—C19—C18	115.19 (11)
C3—C2—H2	120.9	C20—C19—C18	121.24 (12)
O2—C3—C4	114.46 (11)	C19—C20—C21	118.42 (11)
O2—C3—C2	124.28 (11)	C19—C20—H20	120.8
C4—C3—C2	121.26 (11)	C21—C20—H20	120.8
C3—C4—C5	119.91 (11)	O4—C21—C22	115.05 (12)
C3—C4—H4	120.0	O4—C21—C20	123.55 (11)
C5—C4—H4	120.0	C22—C21—C20	121.40 (11)
C4—C5—C6	119.88 (11)	C21—C22—C17	119.40 (12)
C4—C5—C7	118.29 (11)	C21—C22—H22	120.3
C6—C5—C7	121.78 (11)	C17—C22—H22	120.3
C1—C6—C5	119.30 (11)	O1—C23—H23A	109.5
C1—C6—H6	120.4	O1—C23—H23B	109.5
C5—C6—H6	120.4	H23A—C23—H23B	109.5
C8—C7—C5	174.44 (14)	O1—C23—H23C	109.5
C7—C8—C9	179.42 (15)	H23A—C23—H23C	109.5
C14—C9—C10	119.07 (11)	H23B—C23—H23C	109.5
C14—C9—C8	120.64 (11)	O2—C24—H24A	109.5
C10—C9—C8	120.29 (11)	O2—C24—H24B	109.5
C11—C10—C9	120.50 (11)	H24A—C24—H24B	109.5
C11—C10—H10	119.8	O2—C24—H24C	109.5
C9—C10—H10	119.8	H24A—C24—H24C	109.5
C10—C11—C12	120.45 (11)	H24B—C24—H24C	109.5
C10—C11—H11	119.8	O3—C25—H25A	109.5
C12—C11—H11	119.8	O3—C25—H25B	109.5
C11—C12—C13	119.00 (11)	H25A—C25—H25B	109.5
C11—C12—C15	121.46 (11)	O3—C25—H25C	109.5
C13—C12—C15	119.54 (11)	H25A—C25—H25C	109.5
C14—C13—C12	120.58 (11)	H25B—C25—H25C	109.5
C14—C13—H13	119.7	O4—C26—H26A	109.5
C12—C13—H13	119.7	O4—C26—H26B	109.5
C13—C14—C9	120.39 (12)	H26A—C26—H26B	109.5
C13—C14—H14	119.8	O4—C26—H26C	109.5
C9—C14—H14	119.8	H26A—C26—H26C	109.5
C16—C15—C12	177.95 (14)	H26B—C26—H26C	109.5
C15—C16—C17	177.90 (14)	C1—O1—C23	118.13 (10)
C22—C17—C18	120.08 (11)	C3—O2—C24	118.91 (10)
C22—C17—C16	119.31 (12)	C19—O3—C25	117.90 (10)
C18—C17—C16	120.60 (11)	C21—O4—C26	118.72 (11)

O1—C1—C2—C3	177.69 (11)	C8—C9—C14—C13	−179.92 (12)
C6—C1—C2—C3	0.59 (18)	C22—C17—C18—C19	0.2 (2)
C1—C2—C3—O2	179.60 (11)	C16—C17—C18—C19	179.07 (12)
C1—C2—C3—C4	−0.90 (18)	C17—C18—C19—O3	−178.99 (12)
O2—C3—C4—C5	179.63 (11)	C17—C18—C19—C20	0.8 (2)
C2—C3—C4—C5	0.08 (18)	O3—C19—C20—C21	178.44 (12)
C3—C4—C5—C6	1.06 (18)	C18—C19—C20—C21	−1.4 (2)
C3—C4—C5—C7	−176.30 (11)	C19—C20—C21—O4	−178.72 (13)
O1—C1—C6—C5	−176.80 (11)	C19—C20—C21—C22	0.9 (2)
C2—C1—C6—C5	0.53 (19)	O4—C21—C22—C17	179.75 (12)
C4—C5—C6—C1	−1.36 (18)	C20—C21—C22—C17	0.1 (2)
C7—C5—C6—C1	175.90 (11)	C18—C17—C22—C21	−0.6 (2)
C14—C9—C10—C11	−0.84 (19)	C16—C17—C22—C21	−179.55 (12)
C8—C9—C10—C11	179.30 (12)	C6—C1—O1—C23	−179.78 (12)
C9—C10—C11—C12	0.59 (19)	C2—C1—O1—C23	2.94 (18)
C10—C11—C12—C13	0.28 (19)	C4—C3—O2—C24	−175.99 (12)
C10—C11—C12—C15	−179.69 (12)	C2—C3—O2—C24	3.55 (18)
C11—C12—C13—C14	−0.90 (19)	C20—C19—O3—C25	−1.8 (2)
C15—C12—C13—C14	179.07 (12)	C18—C19—O3—C25	178.03 (12)
C12—C13—C14—C9	0.65 (19)	C22—C21—O4—C26	179.71 (14)
C10—C9—C14—C13	0.22 (19)	C20—C21—O4—C26	−0.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4ⁱ	0.95	2.42	3.3511 (17)	167
C14—H14···O2ⁱⁱ	0.95	2.37	3.2758 (16)	160

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₂O₄
M_r	398.44
Crystal system, space group	Monoclinic, P2₁/a
Temperature (K)	173
a, b, c (Å)	8.8980 (5), 19.4610 (8), 12.2820 (5)
β (°)	100.607 (1)
V (Å³)	2090.46 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.15

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15238, 4638, 3914
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.140, 1.11
No. of reflections	4638
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.17

Computer programs: CrystalClear (Rigaku, 2001), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4ⁱ	0.95	2.42	3.3511 (17)	167
C14—H14···O2ⁱⁱ	0.95	2.37	3.2758 (16)	160

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

Acknowledgements

This work was supported by a Grant-in-Aid for Scientific Research (grant No. 19550034) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. The authors thank the Instrument Center of the Institute for Molecular Science for the X-ray structure analysis.

References

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