2,7-Bis(4-acetyl­phen­oxy)naphthalene

Nakaema, K.; Imaizumi, M.; Noguchi, K.; Yonezawa, N.

doi:10.1107/S1600536808007496

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o747

doi:10.1107/S1600536808007496

Open

access

2,7-Bis(4-acetylphenoxy)naphthalene

Kosuke Nakaema,^a Masahiro Imaizumi,^b Keiichi Noguchi ^c and Noriyuki Yonezawa ^a ^*

^aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, Koganei, Tokyo 184-8588, Japan, ^bSection Manager, Group I, Section III, Functional Chemicals Research Laboratory, Nippon Kayaku Co. Ltd, Shimo 3-chome, Kita-ku, Tokyo 115-0042, Japan, and ^cInstrumentation Analysis Center, Tokyo University of Agriculture & Technology, Koganei, Tokyo 184-8588, Japan
^*Correspondence e-mail: yonezawa@cc.tuat.ac.jp

(Received 10 March 2008; accepted 19 March 2008; online 29 March 2008)

The title compound, C₂₆H₂₀O₄, has an asymmetrical conformation at 193 K. The 4-acetylphenyl groups are twisted away from the the naphthalene ring system, with one benzene ring turned towards the 1-position of the naphthalene ring and the other benzene ring turned towards the 6-position. The interplanar angles between the mean planes of the benzene rings and the naphthalene ring system are 68.71 (6) and 74.01 (6)°. The structure displays C—H⋯O hydrogen bonding and π–π stacking interactions [centroid–centroid and interplanar distances are 3.5938 (9) and 3.517 Å, respectively].

Related literature

For related literature, see: Ocak et al. (2004 ).

Experimental

Crystal data

C₂₆H₂₀O₄
M_r = 396.42
Triclinic, $[P \overline 1]$
a = 5.8691 (2) Å
b = 7.9105 (2) Å
c = 21.4040 (5) Å
α = 90.322 (2)°
β = 95.534 (2)°
γ = 102.283 (2)°
V = 966.11 (5) Å³
Z = 2
Cu Kα radiation
μ = 0.74 mm⁻¹
T = 193 K
0.60 × 0.20 × 0.02 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.792, T_max = 0.985
17040 measured reflections
3467 independent reflections
2617 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.125
S = 1.09
3467 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.95	2.54	3.448 (2)	160
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SIR2004 (Burla, et al, 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007496/fl2193sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007496/fl2193Isup2.hkl

checkCIF report

Comment top

An ORTEPIII (Burnett & Johnson, 1996) plot of the molecule (I) is shown in Fig. 1.Considering its two dimensional representation, the molecule could have had C₂ symmetry. This is certainly not the case in practice, as the naphthalene moiety forms dihedral angles of 68.71 (6)° and 74.01 (6)° with the best mean planes of the aromatic rings C11—C16 and C19—C24, respectively. The torsion angles between the naphthalene ring and the two benzene rings are -34.0 (2)° [C11—O1—C1—C2], and -132.00 (15)° [C19—O3—C5—C4]. The difference in the two torsion angles between the naphthalene and benzene rings is rather large. This means that one benzene ring (C11—C16) turns to the 1-position, and the other benzene ring (C19—C24) turns to the 6-position rather than the 8-position. This compound has an asymmetrical conformation similar to that of 2,7-bis(3,4-dicyanophenoxy)naphthalene (Ocak et al., 2004).

The crystal packing is stabilized mainly by van der Waals interactions, however there is some π—π stacking and C—H···O intermolecular interactions (Table 1, Fig. 2). The hydrogen bonds between an acetyl hydrogen and the carbonyl oxygen of a neighboring molecule link the molecules into pairs around a center of symmetry that are aligned complementarily in a row forming a polymer-like infinitive ribbon (Fig. 2).

Related literature top

For related literature, see: Ocak et al. (2004).

Experimental top

2,7-naphthalenediol (160 mg, 1.0 mmol) and 4-fluoroacetophenone (303 mg, 2.2 mmol) were dissolved in DMF (1.0 ml) with stirring under N₂. Potassium carbonate (304 mg, 2.2 mmol) was added. The reaction mixture was stirred for 24 h at 150 C° and poured into water. The products extracted with CHCl₃, and washed with brine. The organic layer was dried with MgSO₄ and concentrated under pressure. Slightly purplish single crystals suitable for X-ray diffraction were obtained by crystallization from ethanol.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR2004 (Burla, et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), with the atom-labeling scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound, viewed down the a axis. The dashed lines indicate hydrogen bonding (blue dashed line) and π—π stacking interactions (black dashed line).

2,7-Bis(4-acetylphenoxy)naphthalene top

Crystal data top

C₂₆H₂₀O₄	Z = 2
M_r = 396.42	F(000) = 416
Triclinic, P1	D_x = 1.363 Mg m⁻³
Hall symbol: -P 1	Melting point = 430.2–430.9 K
a = 5.8691 (2) Å	Cu Kα radiation, λ = 1.54187 Å
b = 7.9105 (2) Å	Cell parameters from 12820 reflections
c = 21.4040 (5) Å	θ = 4.2–68.2°
α = 90.322 (2)°	µ = 0.74 mm⁻¹
β = 95.534 (2)°	T = 193 K
γ = 102.283 (2)°	Platelet, clear pale purple
V = 966.11 (5) Å³	0.60 × 0.20 × 0.02 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3467 independent reflections
Radiation source: rotating anode	2617 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.2°, θ_min = 4.2°
ω scans	h = −6→6
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −9→9
T_min = 0.792, T_max = 0.985	l = −25→25
17040 measured 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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F²) = 0.125	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0673P)² + 0.0881P] where P = (F_o² + 2F_c²)/3
3467 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₆H₂₀O₄	γ = 102.283 (2)°
M_r = 396.42	V = 966.11 (5) Å³
Triclinic, P1	Z = 2
a = 5.8691 (2) Å	Cu Kα radiation
b = 7.9105 (2) Å	µ = 0.74 mm⁻¹
c = 21.4040 (5) Å	T = 193 K
α = 90.322 (2)°	0.60 × 0.20 × 0.02 mm
β = 95.534 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3467 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2617 reflections with I > 2σ(I)
T_min = 0.792, T_max = 0.985	R_int = 0.030
17040 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.09	Δρ_max = 0.19 e Å⁻³
3467 reflections	Δρ_min = −0.24 e Å⁻³
273 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
O1	0.4929 (2)	0.04326 (15)	0.14405 (5)	0.0460 (3)
O2	0.7532 (2)	0.44294 (17)	−0.10302 (6)	0.0578 (4)
O3	−0.3337 (2)	0.45641 (15)	0.28446 (5)	0.0445 (3)
O4	−0.6274 (2)	0.81543 (16)	0.51905 (6)	0.0542 (4)
C1	0.3180 (3)	0.0478 (2)	0.18309 (7)	0.0364 (4)
C2	0.2243 (3)	0.1895 (2)	0.19006 (7)	0.0363 (4)
H2	0.2721	0.2894	0.1661	0.044*
C3	0.0555 (3)	0.18698 (19)	0.23309 (6)	0.0334 (4)
C4	−0.0519 (3)	0.3297 (2)	0.24098 (7)	0.0361 (4)
H4	−0.0100	0.4308	0.2173	0.043*
C5	−0.2151 (3)	0.3208 (2)	0.28259 (7)	0.0376 (4)
C6	−0.2807 (3)	0.1748 (2)	0.31916 (7)	0.0416 (4)
H6	−0.3939	0.1724	0.3482	0.050*
C7	−0.1796 (3)	0.0366 (2)	0.31236 (7)	0.0402 (4)
H7	−0.2233	−0.0622	0.3371	0.048*
C8	−0.0113 (3)	0.03715 (19)	0.26930 (6)	0.0344 (4)
C9	0.0924 (3)	−0.1059 (2)	0.26025 (7)	0.0410 (4)
H9	0.0496	−0.2065	0.2841	0.049*
C10	0.2526 (3)	−0.1022 (2)	0.21793 (7)	0.0407 (4)
H10	0.3194	−0.1997	0.2120	0.049*
C11	0.4961 (3)	0.13361 (19)	0.08868 (7)	0.0361 (4)
C12	0.2975 (3)	0.1256 (2)	0.04757 (7)	0.0402 (4)
H12	0.1489	0.0664	0.0586	0.048*
C13	0.3166 (3)	0.2042 (2)	−0.00971 (7)	0.0395 (4)
H13	0.1800	0.1984	−0.0380	0.047*
C14	0.5327 (3)	0.29172 (18)	−0.02654 (7)	0.0341 (4)
C15	0.7292 (3)	0.3012 (2)	0.01629 (7)	0.0393 (4)
H15	0.8777	0.3623	0.0059	0.047*
C16	0.7120 (3)	0.2230 (2)	0.07376 (7)	0.0392 (4)
H16	0.8473	0.2307	0.1027	0.047*
C17	0.5597 (3)	0.3703 (2)	−0.08936 (7)	0.0403 (4)
C18	0.3482 (3)	0.3545 (2)	−0.13569 (8)	0.0510 (5)
H18A	0.3925	0.4167	−0.1736	0.061*
H18B	0.2301	0.4043	−0.1172	0.061*
H18C	0.2835	0.2321	−0.1466	0.061*
C19	−0.3525 (3)	0.52941 (19)	0.34179 (7)	0.0359 (4)
C20	−0.1817 (3)	0.5418 (2)	0.39204 (7)	0.0404 (4)
H20	−0.0502	0.4910	0.3891	0.049*
C21	−0.2046 (3)	0.6289 (2)	0.44668 (7)	0.0409 (4)
H21	−0.0859	0.6398	0.4808	0.049*
C22	−0.3988 (3)	0.70055 (19)	0.45228 (7)	0.0359 (4)
C23	−0.5678 (3)	0.6862 (2)	0.40098 (7)	0.0408 (4)
H23	−0.7010	0.7351	0.4039	0.049*
C24	−0.5448 (3)	0.6021 (2)	0.34601 (7)	0.0398 (4)
H24	−0.6606	0.5942	0.3113	0.048*
C25	−0.4346 (3)	0.7891 (2)	0.51118 (7)	0.0407 (4)
C26	−0.2330 (3)	0.8422 (3)	0.56052 (8)	0.0545 (5)
H26A	−0.2649	0.9313	0.5884	0.065*
H26B	−0.0902	0.8885	0.5405	0.065*
H26C	−0.2117	0.7415	0.5851	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0475 (7)	0.0581 (7)	0.0407 (6)	0.0246 (6)	0.0160 (5)	0.0149 (5)
O2	0.0560 (8)	0.0639 (8)	0.0516 (7)	0.0043 (6)	0.0144 (6)	0.0169 (6)
O3	0.0530 (7)	0.0528 (7)	0.0338 (6)	0.0234 (6)	0.0082 (5)	0.0020 (5)
O4	0.0503 (8)	0.0594 (8)	0.0558 (7)	0.0128 (6)	0.0184 (6)	−0.0041 (6)
C1	0.0351 (9)	0.0458 (9)	0.0299 (8)	0.0113 (7)	0.0054 (6)	0.0031 (6)
C2	0.0380 (9)	0.0388 (9)	0.0315 (8)	0.0067 (7)	0.0041 (6)	0.0051 (6)
C3	0.0338 (8)	0.0389 (8)	0.0266 (7)	0.0062 (7)	0.0010 (6)	0.0007 (6)
C4	0.0395 (9)	0.0370 (8)	0.0311 (8)	0.0064 (7)	0.0038 (6)	0.0030 (6)
C5	0.0385 (9)	0.0427 (9)	0.0332 (8)	0.0127 (7)	0.0025 (6)	−0.0026 (6)
C6	0.0407 (10)	0.0492 (10)	0.0352 (8)	0.0070 (8)	0.0117 (7)	0.0014 (7)
C7	0.0418 (10)	0.0405 (9)	0.0364 (8)	0.0029 (7)	0.0073 (7)	0.0050 (7)
C8	0.0338 (9)	0.0388 (8)	0.0294 (7)	0.0054 (7)	0.0024 (6)	0.0014 (6)
C9	0.0466 (10)	0.0372 (9)	0.0383 (8)	0.0063 (7)	0.0058 (7)	0.0059 (7)
C10	0.0464 (10)	0.0401 (9)	0.0386 (9)	0.0151 (7)	0.0063 (7)	0.0032 (7)
C11	0.0411 (9)	0.0378 (8)	0.0328 (8)	0.0136 (7)	0.0087 (7)	0.0033 (6)
C12	0.0335 (9)	0.0448 (9)	0.0413 (9)	0.0034 (7)	0.0099 (7)	0.0014 (7)
C13	0.0352 (9)	0.0461 (9)	0.0363 (8)	0.0075 (7)	0.0021 (7)	−0.0014 (7)
C14	0.0375 (9)	0.0310 (8)	0.0349 (8)	0.0085 (6)	0.0064 (6)	−0.0014 (6)
C15	0.0339 (9)	0.0390 (9)	0.0438 (9)	0.0031 (7)	0.0085 (7)	0.0023 (7)
C16	0.0341 (9)	0.0466 (9)	0.0375 (8)	0.0106 (7)	0.0025 (7)	0.0004 (7)
C17	0.0483 (10)	0.0364 (8)	0.0390 (9)	0.0126 (7)	0.0103 (7)	0.0020 (7)
C18	0.0608 (12)	0.0583 (11)	0.0380 (9)	0.0221 (9)	0.0049 (8)	0.0060 (8)
C19	0.0377 (9)	0.0370 (8)	0.0346 (8)	0.0083 (7)	0.0103 (7)	0.0032 (6)
C20	0.0353 (9)	0.0462 (9)	0.0426 (9)	0.0143 (7)	0.0053 (7)	0.0019 (7)
C21	0.0388 (9)	0.0459 (9)	0.0390 (9)	0.0123 (7)	0.0019 (7)	0.0027 (7)
C22	0.0358 (9)	0.0335 (8)	0.0383 (8)	0.0053 (6)	0.0079 (7)	0.0031 (6)
C23	0.0332 (9)	0.0433 (9)	0.0478 (9)	0.0103 (7)	0.0081 (7)	0.0022 (7)
C24	0.0345 (9)	0.0446 (9)	0.0411 (9)	0.0110 (7)	0.0020 (7)	0.0016 (7)
C25	0.0445 (10)	0.0369 (8)	0.0418 (9)	0.0073 (7)	0.0129 (7)	0.0054 (7)
C26	0.0574 (12)	0.0635 (12)	0.0432 (10)	0.0149 (9)	0.0048 (8)	−0.0075 (8)

Geometric parameters (Å, º) top

O1—C11	1.3871 (17)	C13—C14	1.391 (2)
O1—C1	1.3905 (17)	C13—H13	0.9500
O2—C17	1.2225 (18)	C14—C15	1.391 (2)
O3—C19	1.3772 (17)	C14—C17	1.492 (2)
O3—C5	1.4001 (18)	C15—C16	1.383 (2)
O4—C25	1.2201 (19)	C15—H15	0.9500
C1—C2	1.363 (2)	C16—H16	0.9500
C1—C10	1.408 (2)	C17—C18	1.495 (2)
C2—C3	1.413 (2)	C18—H18A	0.9800
C2—H2	0.9500	C18—H18B	0.9800
C3—C4	1.422 (2)	C18—H18C	0.9800
C3—C8	1.425 (2)	C19—C24	1.381 (2)
C4—C5	1.361 (2)	C19—C20	1.386 (2)
C4—H4	0.9500	C20—C21	1.386 (2)
C5—C6	1.405 (2)	C20—H20	0.9500
C6—C7	1.363 (2)	C21—C22	1.391 (2)
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.414 (2)	C22—C23	1.394 (2)
C7—H7	0.9500	C22—C25	1.493 (2)
C8—C9	1.415 (2)	C23—C24	1.381 (2)
C9—C10	1.363 (2)	C23—H23	0.9500
C9—H9	0.9500	C24—H24	0.9500
C10—H10	0.9500	C25—C26	1.495 (2)
C11—C16	1.381 (2)	C26—H26A	0.9800
C11—C12	1.381 (2)	C26—H26B	0.9800
C12—C13	1.381 (2)	C26—H26C	0.9800
C12—H12	0.9500

C11—O1—C1	119.52 (12)	C13—C14—C17	122.02 (14)
C19—O3—C5	118.88 (11)	C16—C15—C14	121.10 (14)
C2—C1—O1	123.00 (14)	C16—C15—H15	119.5
C2—C1—C10	121.89 (14)	C14—C15—H15	119.5
O1—C1—C10	115.03 (14)	C11—C16—C15	119.34 (15)
C1—C2—C3	119.57 (14)	C11—C16—H16	120.3
C1—C2—H2	120.2	C15—C16—H16	120.3
C3—C2—H2	120.2	O2—C17—C14	120.20 (15)
C2—C3—C4	121.79 (14)	O2—C17—C18	120.69 (14)
C2—C3—C8	119.44 (14)	C14—C17—C18	119.09 (14)
C4—C3—C8	118.76 (13)	C17—C18—H18A	109.5
C5—C4—C3	119.74 (14)	C17—C18—H18B	109.5
C5—C4—H4	120.1	H18A—C18—H18B	109.5
C3—C4—H4	120.1	C17—C18—H18C	109.5
C4—C5—O3	117.97 (14)	H18A—C18—H18C	109.5
C4—C5—C6	122.15 (15)	H18B—C18—H18C	109.5
O3—C5—C6	119.65 (14)	O3—C19—C24	116.52 (14)
C7—C6—C5	119.04 (14)	O3—C19—C20	122.80 (14)
C7—C6—H6	120.5	C24—C19—C20	120.53 (14)
C5—C6—H6	120.5	C19—C20—C21	119.39 (15)
C6—C7—C8	121.46 (14)	C19—C20—H20	120.3
C6—C7—H7	119.3	C21—C20—H20	120.3
C8—C7—H7	119.3	C20—C21—C22	121.00 (15)
C7—C8—C9	122.66 (14)	C20—C21—H21	119.5
C7—C8—C3	118.84 (14)	C22—C21—H21	119.5
C9—C8—C3	118.50 (14)	C21—C22—C23	118.36 (14)
C10—C9—C8	121.31 (14)	C21—C22—C25	122.64 (15)
C10—C9—H9	119.3	C23—C22—C25	118.98 (14)
C8—C9—H9	119.3	C24—C23—C22	121.06 (15)
C9—C10—C1	119.28 (15)	C24—C23—H23	119.5
C9—C10—H10	120.4	C22—C23—H23	119.5
C1—C10—H10	120.4	C23—C24—C19	119.63 (15)
C16—C11—C12	120.70 (14)	C23—C24—H24	120.2
C16—C11—O1	116.81 (14)	C19—C24—H24	120.2
C12—C11—O1	122.32 (14)	O4—C25—C22	120.09 (15)
C11—C12—C13	119.49 (14)	O4—C25—C26	120.68 (15)
C11—C12—H12	120.3	C22—C25—C26	119.22 (14)
C13—C12—H12	120.3	C25—C26—H26A	109.5
C12—C13—C14	121.00 (15)	C25—C26—H26B	109.5
C12—C13—H13	119.5	H26A—C26—H26B	109.5
C14—C13—H13	119.5	C25—C26—H26C	109.5
C15—C14—C13	118.34 (14)	H26A—C26—H26C	109.5
C15—C14—C17	119.62 (14)	H26B—C26—H26C	109.5

C11—O1—C1—C2	−34.0 (2)	O1—C11—C12—C13	−173.43 (14)
C11—O1—C1—C10	149.36 (14)	C11—C12—C13—C14	−0.2 (2)
O1—C1—C2—C3	−176.78 (13)	C12—C13—C14—C15	−1.2 (2)
C10—C1—C2—C3	−0.4 (2)	C12—C13—C14—C17	176.96 (14)
C1—C2—C3—C4	−178.38 (14)	C13—C14—C15—C16	1.2 (2)
C1—C2—C3—C8	1.0 (2)	C17—C14—C15—C16	−177.04 (14)
C2—C3—C4—C5	179.42 (14)	C12—C11—C16—C15	−1.7 (2)
C8—C3—C4—C5	0.0 (2)	O1—C11—C16—C15	173.65 (13)
C3—C4—C5—O3	−173.71 (12)	C14—C15—C16—C11	0.3 (2)
C3—C4—C5—C6	0.7 (2)	C15—C14—C17—O2	−0.2 (2)
C19—O3—C5—C4	−132.00 (15)	C13—C14—C17—O2	−178.38 (14)
C19—O3—C5—C6	53.40 (19)	C15—C14—C17—C18	178.13 (14)
C4—C5—C6—C7	−0.7 (2)	C13—C14—C17—C18	0.0 (2)
O3—C5—C6—C7	173.69 (14)	C5—O3—C19—C24	−152.32 (14)
C5—C6—C7—C8	−0.2 (2)	C5—O3—C19—C20	32.1 (2)
C6—C7—C8—C9	−178.51 (14)	O3—C19—C20—C21	175.05 (14)
C6—C7—C8—C3	0.9 (2)	C24—C19—C20—C21	−0.4 (2)
C2—C3—C8—C7	179.76 (13)	C19—C20—C21—C22	1.4 (2)
C4—C3—C8—C7	−0.8 (2)	C20—C21—C22—C23	−1.5 (2)
C2—C3—C8—C9	−0.8 (2)	C20—C21—C22—C25	177.50 (14)
C4—C3—C8—C9	178.62 (13)	C21—C22—C23—C24	0.4 (2)
C7—C8—C9—C10	179.34 (14)	C25—C22—C23—C24	−178.56 (14)
C3—C8—C9—C10	−0.1 (2)	C22—C23—C24—C19	0.6 (2)
C8—C9—C10—C1	0.7 (2)	O3—C19—C24—C23	−176.32 (13)
C2—C1—C10—C9	−0.5 (2)	C20—C19—C24—C23	−0.6 (2)
O1—C1—C10—C9	176.16 (13)	C21—C22—C25—O4	−163.64 (15)
C1—O1—C11—C16	137.94 (14)	C23—C22—C25—O4	15.3 (2)
C1—O1—C11—C12	−46.8 (2)	C21—C22—C25—C26	15.4 (2)
C16—C11—C12—C13	1.7 (2)	C23—C22—C25—C26	−165.70 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.95	2.54	3.448 (2)	160

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀O₄
M_r	396.42
Crystal system, space group	Triclinic, P1
Temperature (K)	193
a, b, c (Å)	5.8691 (2), 7.9105 (2), 21.4040 (5)
α, β, γ (°)	90.322 (2), 95.534 (2), 102.283 (2)
V (Å³)	966.11 (5)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.60 × 0.20 × 0.02

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.792, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	17040, 3467, 2617
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.125, 1.09
No. of reflections	3467
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.24

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla, et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.95	2.54	3.448 (2)	160

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

This work was partially supported by the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Ocak, N., Işık, Ş., Akdemir, N., Ağar, E. & Gümrükçüoğlu, I. E. (2004). Acta Cryst. E60, o435–o436. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar