[2,7-Dimethoxy-8-(4-methylbenzoyl)-1-naphthyl](4-methylphenyl)methanone

Muto, T.; Kato, Y.; Nagasawa, A.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536810039620

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2752

https://doi.org/10.1107/S1600536810039620

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[2,7-Dimethoxy-8-(4-methylbenzoyl)-1-naphthyl](4-methylphenyl)methanone

Toyokazu Muto,^a Yuichi Kato,^a Atsushi Nagasawa,^a Akiko Okamoto ^a and Noriyuki Yonezawa ^a ^*

^aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan
^*Correspondence e-mail: yonezawa@cc.tuat.ac.jp

(Received 29 September 2010; accepted 4 October 2010; online 9 October 2010)

In the title compound, C₂₈H₂₄O₄, the two 4-methylbenzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost antiparallel, the dihedral angle between the two phenyl rings being 9.64 (7)°. The dihedral angles between the two phenyl rings and the naphthalene ring system are 71.82 (6) and 71.58 (6)°. In the crystal, intermolecular C—H⋯O interactions between the carbonyl oxygen and aromatic hydrogen are observed.

Related literature

For the formation reaction of aroylated naphthalene compounds via electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, see: Okamoto & Yonezawa (2009 ). For related structures, see: Nakaema et al. (2007 , 2008 ); Watanabe et al. (2010a ,b ).

Experimental

Crystal data

C₂₈H₂₄O₄
M_r = 424.47
Orthorhombic, P n a 2₁
a = 20.0334 (3) Å
b = 13.4311 (2) Å
c = 7.94771 (10) Å
V = 2138.49 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.70 mm⁻¹
T = 193 K
0.60 × 0.40 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.604, T_max = 0.873
33150 measured reflections
2110 independent reflections
2041 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.094
S = 1.17
2110 reflections
293 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 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
C14—H14⋯O1ⁱ	0.95	2.52	3.465 (3)	175
C21—H21⋯O2ⁱⁱ	0.95	2.38	3.295 (3)	162
Symmetry codes: (i) x, y, z-1; (ii) x, y, z+1.

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 I, global. DOI: https://doi.org/10.1107/S1600536810039620/om2367sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039620/om2367Isup2.hkl

checkCIF report

Comment top

In the course of our study on selective electrophilic aromatic aroylation of the naphthalene core, peri-aroylnaphthalene compounds have proved to be formed regioselectively by the aid of a suitable acidic mediator (Okamoto & Yonezawa, 2009). Recently, we reported the X-ray crystal structures of 1,8-diaroylated 2,7-dimethoxynaphthalene derivatives such as 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al., 2007), 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008), bis(4-bromophenyl)(2,7-dimethoxynaphthalene-1,8-diyl)dimethanone [1,8-bis(4-bromobenzoyl)-2,7-dimethoxynaphthalene] (Watanabe et al., 2010a) and (2,7-dimethoxynaphthalene-1,8-diyl)bis(4-fluorophenyl) dimethanone [1,8-bis(4-fluorobenzoyl)-2,7-dimethoxynaphthalene] (Watanabe et al., 2010b). The aroyl groups at 1,8-positions of the naphthalene rings in these compounds are oriented in opposite direction. The aromatic rings in the molecule are non-coplanar, resulting in partial disruption of π-conjugation of ring systems. As a part of our continuing studies on the molecular structures of this kind of homologous molecules, the X-ray crystal structure of title compound, peri-aroylnaphthalene bearing methyl groups, is discussed in this article.

The molecular structure of the title compound is displayed in Fig 1. Two 4-methylbenzoyl groups are situated in anti orientation and are twisted away from the attached naphthalene ring. The interplanar angle between the best planes of the two phenyl rings is 9.64 (7)°. On the other hand, the two interplanar angles between the best planes of the 4-methylphenyl rings and the naphthalene ring are 71.82 (6) and 71.58 (6)°, respectively. The torsion angles between the carbonyl groups and the naphthalene ring [C10—C1—C11—O1 = 68.1 (2)° and C10—C9—C18—O2 = 67.6 (2)°] are larger than those between the carbonyl groups and 4-methylphenyl groups [O1—C11—C12—C13 = -179.18 (15)° and O2—C18—C19—C20 = 176.67 (15)°]. In the molecular packing, the C—H···O hydrogen interactions between the oxygen atoms of the carbonyl groups and the hydrogen atoms of the phenyl rings are observed along the c axis [C14—H14···O1 = 2.52 Å and C21—H21···O2 = 2.38 Å] (Fig. 2).

Related literature top

For the formation of aroylated naphthalene compounds via electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, see: Okamoto & Yonezawa (2009). For related structures, see: Nakaema et al. (2007, 2008); Watanabe et al. (2010a,b).

Experimental top

To a 30 ml flask, 4-methylbenzoic acid (8.00 mmol, 1.08 g) and phosphorus pentoxide–methanesulfonic acid mixture (P₂O₅–MsOH; 8.0 ml) were placed and stirred at 333 K. To the solution thus obtained, 2,7-dimethoxynaphthalene (4.00 mmol, 0.752 g) was added. After the reaction mixture was stirred at 333 K for 2 h, it was poured into ice-cold water (10 ml) and the mixture was extracted with CHCl₃ (10 ml × 3). The combined extracts were washed with 2 M aqueous NaOH followed by washing with brine. The organic layer was dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give a cake (57% yield). The crude product was purified by recrystallization from CHCl₃-hexane (isolated yield 35%). Furthermore, the isolated product was crystallized from EtOH to give single-crystals.

Spectral data:¹H NMR δ (300 MHz, CDCl₃): 2.37 (6H, s), 3.67 (6H, s), 7.11 (4H, d, J = 7.8 Hz), 7.19 (2H, d, J = 8.7 Hz), 7.57 (4H, d, J = 7.8 Hz), 7.92 (2H, d, J = 8.7 Hz). ¹³C NMR δ (300 MHz, CDCl₃): 21.740, 56.495, 111.34, 121.91, 125.58, 128.70, 129.25, 129.74, 131.79, 136.31, 143.17, 156.12, 196.22. IR (KBr): 1655 (C═O), 1607, 1512 (Ar, naphthalene). m.p. = 531.8–534.9 K. Anal. Calcd for C₂₈H₂₄O₄; C, 79.22; H, 5,70. Found C, 78.98; H, 5.78.

Structure description top

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 with the atom-labeling scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. : C—H···O interactions (dashed lines).

[2,7-Dimethoxy-8-(4-methylbenzoyl)-1-naphthyl](4-methylphenyl)methanone top

Crystal data top

C₂₈H₂₄O₄	F(000) = 896
M_r = 424.47	D_x = 1.318 Mg m⁻³
Orthorhombic, Pna2₁	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2c -2n	Cell parameters from 31782 reflections
a = 20.0334 (3) Å	θ = 3.3–68.2°
b = 13.4311 (2) Å	µ = 0.70 mm⁻¹
c = 7.94771 (10) Å	T = 193 K
V = 2138.49 (5) Å³	Block, colorless
Z = 4	0.60 × 0.40 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2110 independent reflections
Radiation source: fine-focus sealed tube	2041 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.2°, θ_min = 4.0°
ω scans	h = −24→24
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −16→16
T_min = 0.604, T_max = 0.873	l = −9→9
33150 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0569P)² + 0.3088P] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max = 0.002
2110 reflections	Δρ_max = 0.18 e Å⁻³
293 parameters	Δρ_min = −0.17 e Å⁻³
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0066 (5)

Crystal data top

C₂₈H₂₄O₄	V = 2138.49 (5) Å³
M_r = 424.47	Z = 4
Orthorhombic, Pna2₁	Cu Kα radiation
a = 20.0334 (3) Å	µ = 0.70 mm⁻¹
b = 13.4311 (2) Å	T = 193 K
c = 7.94771 (10) Å	0.60 × 0.40 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2110 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2041 reflections with I > 2σ(I)
T_min = 0.604, T_max = 0.873	R_int = 0.034
33150 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	1 restraint
wR(F²) = 0.094	H-atom parameters constrained
S = 1.17	Δρ_max = 0.18 e Å⁻³
2110 reflections	Δρ_min = −0.17 e Å⁻³
293 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	0.14819 (8)	0.11387 (12)	0.5115 (2)	0.0340 (4)
O2	0.14078 (8)	0.32719 (13)	0.2589 (2)	0.0368 (4)
O3	0.06372 (8)	−0.05143 (12)	0.2673 (3)	0.0449 (4)
O4	0.03319 (8)	0.46452 (13)	0.4971 (3)	0.0444 (4)
C1	0.05479 (10)	0.11760 (16)	0.3328 (3)	0.0300 (5)
C2	0.02338 (11)	0.02950 (17)	0.2891 (3)	0.0361 (5)
C3	−0.04660 (12)	0.0239 (2)	0.2705 (4)	0.0426 (6)
H3	−0.0672	−0.0361	0.2345	0.051*
C4	−0.08397 (11)	0.1059 (2)	0.3048 (3)	0.0420 (6)
H4	−0.1311	0.1020	0.2935	0.050*
C5	−0.05501 (10)	0.19654 (19)	0.3567 (3)	0.0369 (5)
C6	−0.09500 (11)	0.2789 (2)	0.4003 (4)	0.0436 (6)
H6	−0.1422	0.2727	0.3944	0.052*
C7	−0.06805 (12)	0.3673 (2)	0.4509 (4)	0.0428 (6)
H7	−0.0960	0.4215	0.4816	0.051*
C8	0.00175 (12)	0.37696 (17)	0.4567 (3)	0.0361 (5)
C9	0.04339 (10)	0.29876 (17)	0.4152 (3)	0.0303 (5)
C10	0.01624 (10)	0.20501 (17)	0.3670 (3)	0.0309 (5)
C11	0.12923 (11)	0.11221 (15)	0.3659 (3)	0.0282 (5)
C12	0.17684 (11)	0.10505 (15)	0.2237 (3)	0.0274 (5)
C13	0.15505 (11)	0.10444 (17)	0.0569 (3)	0.0330 (5)
H13	0.1086	0.1075	0.0330	0.040*
C14	0.20036 (12)	0.09938 (16)	−0.0735 (3)	0.0343 (5)
H14	0.1847	0.0991	−0.1863	0.041*
C15	0.26866 (11)	0.09473 (16)	−0.0420 (3)	0.0332 (5)
C16	0.29032 (11)	0.09517 (17)	0.1250 (3)	0.0343 (5)
H16	0.3367	0.0916	0.1486	0.041*
C17	0.24524 (11)	0.10078 (15)	0.2565 (3)	0.0314 (5)
H17	0.2609	0.1017	0.3693	0.038*
C18	0.11740 (11)	0.32131 (15)	0.4002 (3)	0.0286 (5)
C19	0.15908 (11)	0.33410 (15)	0.5519 (3)	0.0280 (5)
C20	0.13218 (11)	0.33242 (17)	0.7139 (3)	0.0326 (5)
H20	0.0855	0.3239	0.7283	0.039*
C21	0.17245 (12)	0.34296 (17)	0.8529 (3)	0.0356 (5)
H21	0.1532	0.3424	0.9621	0.043*
C22	0.24135 (12)	0.35449 (16)	0.8353 (3)	0.0335 (5)
C23	0.26816 (12)	0.35582 (17)	0.6736 (3)	0.0345 (5)
H23	0.3149	0.3638	0.6594	0.041*
C24	0.22803 (11)	0.34573 (16)	0.5340 (3)	0.0301 (5)
H24	0.2473	0.3467	0.4248	0.036*
C25	0.03540 (14)	−0.14711 (18)	0.2950 (4)	0.0489 (7)
H25A	0.0694	−0.1983	0.2755	0.059*
H25B	−0.0020	−0.1573	0.2173	0.059*
H25C	0.0193	−0.1516	0.4111	0.059*
C26	−0.00659 (15)	0.5493 (2)	0.5335 (5)	0.0575 (8)
H26A	0.0224	0.6057	0.5614	0.069*
H26B	−0.0358	0.5348	0.6292	0.069*
H26C	−0.0338	0.5661	0.4350	0.069*
C27	0.31772 (13)	0.0894 (2)	−0.1857 (4)	0.0450 (6)
H27A	0.2936	0.0769	−0.2909	0.054*
H27B	0.3495	0.0353	−0.1654	0.054*
H27C	0.3419	0.1527	−0.1942	0.054*
C28	0.28470 (13)	0.3658 (2)	0.9887 (4)	0.0442 (6)
H28A	0.2668	0.3247	1.0802	0.053*
H28B	0.2853	0.4357	1.0238	0.053*
H28C	0.3302	0.3442	0.9622	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0338 (8)	0.0407 (9)	0.0276 (9)	−0.0016 (6)	−0.0026 (7)	0.0006 (7)
O2	0.0351 (9)	0.0514 (10)	0.0238 (9)	−0.0047 (7)	0.0037 (7)	0.0015 (7)
O3	0.0372 (8)	0.0403 (9)	0.0573 (11)	−0.0093 (7)	0.0077 (8)	−0.0081 (9)
O4	0.0402 (9)	0.0398 (9)	0.0532 (12)	0.0093 (7)	0.0005 (9)	−0.0030 (8)
C1	0.0260 (10)	0.0401 (11)	0.0237 (10)	−0.0036 (8)	0.0020 (9)	0.0017 (9)
C2	0.0338 (11)	0.0455 (12)	0.0289 (12)	−0.0074 (9)	0.0028 (10)	−0.0013 (10)
C3	0.0353 (11)	0.0551 (14)	0.0374 (13)	−0.0168 (11)	−0.0020 (11)	−0.0008 (12)
C4	0.0258 (10)	0.0635 (16)	0.0368 (14)	−0.0094 (10)	−0.0037 (10)	0.0080 (12)
C5	0.0262 (10)	0.0545 (13)	0.0300 (12)	−0.0008 (10)	−0.0020 (10)	0.0094 (11)
C6	0.0239 (10)	0.0633 (15)	0.0437 (15)	0.0035 (10)	−0.0006 (10)	0.0122 (12)
C7	0.0313 (11)	0.0558 (14)	0.0414 (14)	0.0125 (10)	0.0054 (11)	0.0095 (12)
C8	0.0361 (11)	0.0434 (12)	0.0286 (12)	0.0050 (10)	0.0008 (10)	0.0041 (10)
C9	0.0263 (10)	0.0402 (11)	0.0244 (11)	0.0029 (8)	−0.0013 (9)	0.0046 (9)
C10	0.0267 (10)	0.0443 (12)	0.0218 (10)	−0.0018 (9)	−0.0003 (9)	0.0057 (9)
C11	0.0302 (11)	0.0267 (9)	0.0275 (12)	−0.0023 (8)	−0.0017 (10)	0.0005 (9)
C12	0.0264 (10)	0.0272 (9)	0.0286 (12)	−0.0021 (7)	−0.0009 (9)	−0.0001 (8)
C13	0.0281 (11)	0.0408 (12)	0.0303 (12)	−0.0005 (9)	−0.0048 (9)	0.0018 (10)
C14	0.0387 (12)	0.0381 (11)	0.0262 (11)	0.0005 (9)	−0.0004 (10)	0.0009 (9)
C15	0.0360 (12)	0.0292 (10)	0.0344 (13)	−0.0012 (9)	0.0046 (10)	0.0012 (9)
C16	0.0267 (11)	0.0370 (11)	0.0393 (13)	−0.0026 (8)	0.0011 (10)	0.0001 (10)
C17	0.0294 (10)	0.0331 (10)	0.0317 (12)	−0.0024 (8)	−0.0034 (9)	0.0007 (10)
C18	0.0304 (10)	0.0279 (9)	0.0276 (12)	0.0009 (8)	0.0023 (9)	0.0013 (8)
C19	0.0298 (10)	0.0264 (10)	0.0277 (11)	0.0009 (8)	0.0005 (9)	0.0010 (8)
C20	0.0291 (10)	0.0398 (12)	0.0289 (12)	−0.0008 (9)	0.0018 (9)	0.0002 (10)
C21	0.0404 (12)	0.0405 (12)	0.0259 (12)	−0.0007 (9)	0.0031 (10)	0.0032 (10)
C22	0.0389 (12)	0.0283 (10)	0.0331 (13)	0.0001 (8)	−0.0061 (11)	0.0012 (9)
C23	0.0300 (11)	0.0341 (11)	0.0393 (14)	−0.0002 (9)	−0.0024 (10)	−0.0005 (10)
C24	0.0310 (10)	0.0312 (10)	0.0280 (11)	0.0014 (8)	0.0044 (10)	−0.0004 (9)
C25	0.0531 (15)	0.0413 (12)	0.0523 (17)	−0.0147 (11)	0.0089 (14)	−0.0081 (12)
C26	0.0583 (16)	0.0509 (15)	0.063 (2)	0.0204 (13)	−0.0051 (16)	−0.0145 (15)
C27	0.0419 (13)	0.0522 (14)	0.0408 (15)	0.0002 (10)	0.0110 (12)	0.0014 (12)
C28	0.0500 (15)	0.0459 (13)	0.0368 (14)	−0.0022 (11)	−0.0114 (12)	0.0028 (12)

Geometric parameters (Å, º) top

O1—C11	1.218 (3)	C15—C16	1.396 (4)
O2—C18	1.219 (3)	C15—C27	1.508 (3)
O3—C2	1.366 (3)	C16—C17	1.384 (3)
O3—C25	1.422 (3)	C16—H16	0.9500
O4—C8	1.372 (3)	C17—H17	0.9500
O4—C26	1.420 (3)	C18—C19	1.477 (3)
C1—C2	1.385 (3)	C19—C20	1.395 (3)
C1—C10	1.431 (3)	C19—C24	1.398 (3)
C1—C11	1.516 (3)	C20—C21	1.375 (3)
C2—C3	1.412 (3)	C20—H20	0.9500
C3—C4	1.359 (4)	C21—C22	1.396 (3)
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.410 (4)	C22—C23	1.393 (3)
C4—H4	0.9500	C22—C28	1.505 (3)
C5—C6	1.409 (4)	C23—C24	1.377 (3)
C5—C10	1.434 (3)	C23—H23	0.9500
C6—C7	1.365 (4)	C24—H24	0.9500
C6—H6	0.9500	C25—H25A	0.9800
C7—C8	1.405 (3)	C25—H25B	0.9800
C7—H7	0.9500	C25—H25C	0.9800
C8—C9	1.381 (3)	C26—H26A	0.9800
C9—C10	1.424 (3)	C26—H26B	0.9800
C9—C18	1.518 (3)	C26—H26C	0.9800
C11—C12	1.482 (3)	C27—H27A	0.9800
C12—C13	1.396 (3)	C27—H27B	0.9800
C12—C17	1.396 (3)	C27—H27C	0.9800
C13—C14	1.379 (3)	C28—H28A	0.9800
C13—H13	0.9500	C28—H28B	0.9800
C14—C15	1.392 (3)	C28—H28C	0.9800
C14—H14	0.9500

C2—O3—C25	117.63 (18)	C15—C16—H16	119.5
C8—O4—C26	118.5 (2)	C16—C17—C12	120.1 (2)
C2—C1—C10	120.23 (19)	C16—C17—H17	119.9
C2—C1—C11	116.73 (18)	C12—C17—H17	119.9
C10—C1—C11	122.48 (18)	O2—C18—C19	121.84 (19)
O3—C2—C1	116.31 (18)	O2—C18—C9	117.41 (19)
O3—C2—C3	122.2 (2)	C19—C18—C9	120.75 (18)
C1—C2—C3	121.5 (2)	C20—C19—C24	118.5 (2)
C4—C3—C2	118.9 (2)	C20—C19—C18	122.2 (2)
C4—C3—H3	120.6	C24—C19—C18	119.2 (2)
C2—C3—H3	120.6	C21—C20—C19	120.8 (2)
C3—C4—C5	122.1 (2)	C21—C20—H20	119.6
C3—C4—H4	118.9	C19—C20—H20	119.6
C5—C4—H4	118.9	C20—C21—C22	120.7 (2)
C6—C5—C4	121.05 (19)	C20—C21—H21	119.6
C6—C5—C10	119.3 (2)	C22—C21—H21	119.6
C4—C5—C10	119.6 (2)	C23—C22—C21	118.4 (2)
C7—C6—C5	122.03 (19)	C23—C22—C28	121.6 (2)
C7—C6—H6	119.0	C21—C22—C28	120.0 (2)
C5—C6—H6	119.0	C24—C23—C22	121.1 (2)
C6—C7—C8	118.9 (2)	C24—C23—H23	119.4
C6—C7—H7	120.5	C22—C23—H23	119.4
C8—C7—H7	120.5	C23—C24—C19	120.4 (2)
O4—C8—C9	115.50 (19)	C23—C24—H24	119.8
O4—C8—C7	122.9 (2)	C19—C24—H24	119.8
C9—C8—C7	121.5 (2)	O3—C25—H25A	109.5
C8—C9—C10	120.40 (18)	O3—C25—H25B	109.5
C8—C9—C18	117.19 (19)	H25A—C25—H25B	109.5
C10—C9—C18	121.89 (18)	O3—C25—H25C	109.5
C9—C10—C1	124.76 (17)	H25A—C25—H25C	109.5
C9—C10—C5	117.74 (19)	H25B—C25—H25C	109.5
C1—C10—C5	117.5 (2)	O4—C26—H26A	109.5
O1—C11—C12	121.7 (2)	O4—C26—H26B	109.5
O1—C11—C1	118.1 (2)	H26A—C26—H26B	109.5
C12—C11—C1	120.25 (19)	O4—C26—H26C	109.5
C13—C12—C17	118.9 (2)	H26A—C26—H26C	109.5
C13—C12—C11	121.6 (2)	H26B—C26—H26C	109.5
C17—C12—C11	119.5 (2)	C15—C27—H27A	109.5
C14—C13—C12	120.5 (2)	C15—C27—H27B	109.5
C14—C13—H13	119.7	H27A—C27—H27B	109.5
C12—C13—H13	119.7	C15—C27—H27C	109.5
C13—C14—C15	120.9 (2)	H27A—C27—H27C	109.5
C13—C14—H14	119.5	H27B—C27—H27C	109.5
C15—C14—H14	119.5	C22—C28—H28A	109.5
C14—C15—C16	118.4 (2)	C22—C28—H28B	109.5
C14—C15—C27	120.4 (2)	H28A—C28—H28B	109.5
C16—C15—C27	121.2 (2)	C22—C28—H28C	109.5
C17—C16—C15	121.0 (2)	H28A—C28—H28C	109.5
C17—C16—H16	119.5	H28B—C28—H28C	109.5

C25—O3—C2—C1	153.3 (3)	C10—C1—C11—O1	67.9 (3)
C25—O3—C2—C3	−25.9 (4)	C2—C1—C11—C12	76.4 (3)
C10—C1—C2—O3	−176.7 (2)	C10—C1—C11—C12	−112.1 (2)
C11—C1—C2—O3	−5.0 (3)	O1—C11—C12—C13	−179.2 (2)
C10—C1—C2—C3	2.5 (4)	C1—C11—C12—C13	0.9 (3)
C11—C1—C2—C3	174.1 (2)	O1—C11—C12—C17	−0.5 (3)
O3—C2—C3—C4	175.7 (3)	C1—C11—C12—C17	179.60 (18)
C1—C2—C3—C4	−3.4 (4)	C17—C12—C13—C14	0.2 (3)
C2—C3—C4—C5	0.7 (4)	C11—C12—C13—C14	178.9 (2)
C3—C4—C5—C6	−176.6 (3)	C12—C13—C14—C15	0.0 (3)
C3—C4—C5—C10	2.8 (4)	C13—C14—C15—C16	0.1 (3)
C4—C5—C6—C7	−180.0 (3)	C13—C14—C15—C27	−179.9 (2)
C10—C5—C6—C7	0.6 (4)	C14—C15—C16—C17	−0.4 (3)
C5—C6—C7—C8	1.1 (4)	C27—C15—C16—C17	179.5 (2)
C26—O4—C8—C9	177.1 (3)	C15—C16—C17—C12	0.7 (3)
C26—O4—C8—C7	−0.4 (4)	C13—C12—C17—C16	−0.6 (3)
C6—C7—C8—O4	176.4 (2)	C11—C12—C17—C16	−179.3 (2)
C6—C7—C8—C9	−1.1 (4)	C8—C9—C18—O2	−104.1 (3)
O4—C8—C9—C10	−178.4 (2)	C10—C9—C18—O2	67.6 (3)
C7—C8—C9—C10	−0.8 (4)	C8—C9—C18—C19	76.7 (3)
O4—C8—C9—C18	−6.6 (3)	C10—C9—C18—C19	−111.6 (2)
C7—C8—C9—C18	171.0 (2)	O2—C18—C19—C20	176.7 (2)
C8—C9—C10—C1	−175.5 (2)	C9—C18—C19—C20	−4.1 (3)
C18—C9—C10—C1	13.1 (4)	O2—C18—C19—C24	−5.0 (3)
C8—C9—C10—C5	2.5 (3)	C9—C18—C19—C24	174.19 (18)
C18—C9—C10—C5	−169.0 (2)	C24—C19—C20—C21	0.6 (3)
C2—C1—C10—C9	179.0 (2)	C18—C19—C20—C21	178.9 (2)
C11—C1—C10—C9	7.9 (4)	C19—C20—C21—C22	−0.7 (3)
C2—C1—C10—C5	1.1 (4)	C20—C21—C22—C23	0.5 (3)
C11—C1—C10—C5	−170.1 (2)	C20—C21—C22—C28	−179.9 (2)
C6—C5—C10—C9	−2.4 (4)	C21—C22—C23—C24	−0.2 (3)
C4—C5—C10—C9	178.2 (2)	C28—C22—C23—C24	−179.8 (2)
C6—C5—C10—C1	175.8 (2)	C22—C23—C24—C19	0.1 (3)
C4—C5—C10—C1	−3.7 (4)	C20—C19—C24—C23	−0.4 (3)
C2—C1—C11—O1	−103.5 (3)	C18—C19—C24—C23	−178.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1ⁱ	0.95	2.52	3.465 (3)	175
C21—H21···O2ⁱⁱ	0.95	2.38	3.295 (3)	162

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₄O₄
M_r	424.47
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	193
a, b, c (Å)	20.0334 (3), 13.4311 (2), 7.94771 (10)
V (Å³)	2138.49 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.60 × 0.40 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.604, 0.873
No. of measured, independent and observed [I > 2σ(I)] reflections	33150, 2110, 2041
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.094, 1.17
No. of reflections	2110
No. of parameters	293
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.17

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
C14—H14···O1ⁱ	0.95	2.52	3.465 (3)	175
C21—H21···O2ⁱⁱ	0.95	2.38	3.295 (3)	162

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

Acknowledgements

The authors express their gratitude to Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture & Technology, for technical advice. This work was partially supported by The Mukai Science and Technology Foundation, Tokyo, Japan.

References

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