[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

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

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

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810039620/om2367sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810039620/om2367Isup2.hkl Contains datablock I

CCDC reference: 799551

checkCIF report

Key indicators

Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.003 Å
R factor = 0.034
wR factor = 0.094
Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.20

Author Response: Light atom non-centrosymmetric structures where anomalous dispersion effects are insignificant, it is unwise to attempt to use unmerged Friedel-related reflections simply to boost the r/p ratio.


Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           68.23
           From the CIF: _reflns_number_total               2110
           Count of symmetry unique reflns         2110
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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.

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