(5-Benzoyl-3,6-dimeth­oxy­naphthalen-2-yl)(phen­yl)methanone

Kato, Y.; Nagasawa, A.; Sasagawa, K.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S160053681101508X

(5-Benzoyl-3,6-dimethoxynaphthalen-2-yl)(phenyl)methanone

Y. Kato, A. Nagasawa, K. Sasagawa, A. Okamoto and N. Yonezawa

The asymmetric unit of the title compound, C₂₆H₂₀O₄, contains two independent conformers. The aromatic rings of the aroyl groups are twisted with respect to the naphthalene ring systems to form dihedral angles of 66.58 (6) and 66.45 (6)° in one conformer, and 75.00 (7) and 81.17 (6)° in the other conformer. The crystal packing is stabilized by weak intermolecular C—H

O hydrogen bonds and by C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053681101508X/rz2585sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053681101508X/rz2585Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S160053681101508X/rz2585Isup3.cml Supplementary material

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Key indicators

Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.002 Å
R factor = 0.039
wR factor = 0.115
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW .gt. 10 Outliers .          2

Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600        118
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         16
PLAT918_ALERT_3_C Reflection(s) # with I(obs) much smaller I(calc)          1

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained Atom Sites ....          4
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 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 electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proven to be formed regioselectively with the aid of suitable acidic mediators (Okamoto & Yonezawa, 2009). Recently, we have reported the crystal structures of several 1,8-diaroylated naphthalene homologues exemplified by 1,8-bis(4-aminobenzoyl)-2,7-dimethoxynaphthalene (Nishijima et al., 2010) and 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008). The aroyl groups at the 1,8-positions of the naphthalene rings in these compounds are connected in an almost perpendicular fashion. In this course, the crystal structures of 1-monoaroylated naphthalene compounds and the β-isomers of 3-monoaroylated compounds have been also clarified such as 1-benzoyl-2,7-dimethoxynaphthalene (Kato, et al., 2010), 1-(3-nitrobenzoyl)-2,7-dimethoxynaphthalene (Kataoka et al., 2010), 3-benzoyl-2,7-dimethoxynaphthalene (Kato et al., 2011), and (3,6-dimethoxy-2-naphthyl)(4-fluorophenyl)methanone (Watanabe et al., 2010). 1-Aroylated naphthalene compounds have been revealed to have essentially the same non-coplanar structure as the 1,8-diaroylated naphthalenes. 3-Substituted aroylnaphthalene compounds are generally regarded to be thermodynamically more stable than the corresponding 1-positioned isomeric molecules, with the aroyl groups connected to the naphthalene rings in a moderately twisted fashion. As a part of our continuous study on the molecular structures of this kind of homologous molecules, the crystal structure of title compound, a 1,6-dibenzoylated naphthalene derivative, is discussed in this paper.

There are two independent conformers in the asymmetric unit of the title compound. The conformers, labeled (I) and (II), are shown in Fig. 1. Each conformer has essentially the same non-coplanar structure, the main difference consisting in the dihedral angles formed by the benzene rings with the naphthalene ring systems. Conformer (II) shows a larger dihedral angle for the benzene ring of the aroyl group at 6-position than that of the benzene ring of the aroyl group at 1-potision [81.17 (6) and 75.00 (7)°], whereas very similar dihedral angles are observed for conformer (I) [66.45 (6) and 66.58 (6)°]. These angles could be compared with those reported for related 1- and 3-monoaroylated naphthalenes, e. g. (2,7-dimethoxynaphthalen-1-yl)(phenyl)methanone (75.34 (7), 86.47 (7) and 76.55 (6)°; Kato et al., 2010) and (3,6-dimethoxynaphthalen-2-yl)(phenyl)methanone (68.32 (5)°; Kato et al., 2011). The torsion angles between the carbonyl groups and the naphthalene ring of conformer (I) are 116.90 (14) (C1—C10—C11—O3) and 48.7 (2)° (C5—C6—C18—O4), those of conformer (II) are 106.70 (17) (C27—C36—C37—O7) and 73.7 (2)° (C31—C32—C44—O8). In the crystal structure, the molecular packing is stabilized mainly by weak two intermolecular C—H···O hydrogen bonds in conformer (I) (Table 1, Fig. 2). Moreover, a C—H···O hydrogen bond between the hydrogen atom of a 2-methoxy group and the oxygen atom of a carbonyl group is observed in conformer (II) (Table 1, Fig. 3). The crystal structure is further stabilized by C—H···π interactions (Table 1). In the crystal structure, conformer (I) and (II) are alternately piled up along a axis as shown in Fig. 4.

Related literature top

For information on the electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009). For the structures of closely related compounds, see: Kataoka et al. (2010); Kato et al. (2010, 2011); Nakaema et al. (2008); Nishijima et al. (2010); Watanabe et al. (2010).

Experimental top

To a 50 ml flask, benzoyl chloride (3.2 mmol, 350 mg), aluminium chloride (3.4 mmo1, 450 mg) and methylene chloride (2.5 ml) were added and stirred at 273 K. To the reaction mixture thus obtained, was then added 3-benzoyl-2,7-dimethoxynaphthalene (1.0 mmol, 294 mg). After the reaction mixture was stirred at 273 K for 72 h, it was poured into ice-cold water (10 ml). The aqueous layer was extracted with CHCl₃ (10 ml × 3). The combined extracts were washed with 2M aqueous NaOH followed by washing with brine. The organic layers thus obtained were dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give cake (quant.). The crude product was purified by recrystallization from ethanol (34% yield). Colourless platelet single crystals suitable for X-ray diffraction analysis were obtained by repeated crystallization from a hexane/chloroform (1:1 v/v) solution. ¹H NMR δ (400 MHz, CDCl₃, p.p.m.); 3.60(3H, s), 3.82(3H, s), 6.88(1H, s), 7.23(1H, d, J = 8.4 Hz), 7.41–7.48(4H, m), 7.54–7.62(2H, m), 7.82–7.87(4H, m), 7.89(1H, d, J = 1.6 Hz), 7.92(1H, d, J = 9.2 Hz). ¹³C NMR δ (75 MHz, CDCl₃, p.p.m.): 55.45, 56.31, 102.36, 110.99, 121.64, 123.35, 128.24, 128.63, 128.94, 129.51, 129.87, 130.26, 132.00, 133.04, 133.54, 134.06, 137.75, 137.94, 156.08, 156.39, 195.77, 197.72. IR (KBr); 1668(C═O), 1624, 1578, 1497(Ar, naphthalene) cm^-1. HRMS (m/z); [M + H]⁺ Calcd for C₂₆H₂₁O₄, 397.1440; found, 397.1444. M.p. = 429.4–431.8 K

Structure description top

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku, 2010); program(s) used to solve structure: IL MILIONE (Burla et al., 2007); 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. The molecular structure of conformers (I) and (II). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Intermolecular C—H···O interactions in conformer (I) [symmetry code: (i) -x+3/2, y-1/2, z; (ii) -x+1, -y+2, -z].
	Fig. 3. Intermolecular C—H···O interactions in conformer (II) [symmetry code: (iii) -x+1, -y+1, -z+1].
	Fig. 4. The alignment of the molecules in the crystal structure, viewed along the a axis [conformer (I) is blue, conformer (II) is red].

(5-Benzoyl-3,6-dimethoxynaphthalen-2-yl)(phenyl)methanone top

Crystal data top

C₂₆H₂₀O₄	Z = 4
M_r = 396.42	F(000) = 832
Triclinic, P1	D_x = 1.301 Mg m⁻³
Hall symbol: -P 1	Melting point = 429.4–431.8 K
a = 8.42828 (15) Å	Cu Kα radiation, λ = 1.54187 Å
b = 12.5953 (2) Å	Cell parameters from 27981 reflections
c = 20.0578 (4) Å	θ = 3.6–68.2°
α = 96.222 (1)°	µ = 0.71 mm⁻¹
β = 99.688 (1)°	T = 193 K
γ = 102.727 (1)°	Platelet, colourless
V = 2023.76 (6) Å³	0.60 × 0.40 × 0.10 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	7263 independent reflections
Radiation source: rotating anode	5957 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 10.000 pixels mm^-1	θ_max = 68.2°, θ_min = 3.6°
ω scans	h = −10→10
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −15→15
T_min = 0.677, T_max = 0.933	l = −23→24
32431 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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0636P)² + 0.2292P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
7263 reflections	Δρ_max = 0.27 e Å⁻³
546 parameters	Δρ_min = −0.21 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0067 (4)

Crystal data top

C₂₆H₂₀O₄	γ = 102.727 (1)°
M_r = 396.42	V = 2023.76 (6) Å³
Triclinic, P1	Z = 4
a = 8.42828 (15) Å	Cu Kα radiation
b = 12.5953 (2) Å	µ = 0.71 mm⁻¹
c = 20.0578 (4) Å	T = 193 K
α = 96.222 (1)°	0.60 × 0.40 × 0.10 mm
β = 99.688 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	7263 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	5957 reflections with I > 2σ(I)
T_min = 0.677, T_max = 0.933	R_int = 0.031
32431 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	2 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.08	Δρ_max = 0.27 e Å⁻³
7263 reflections	Δρ_min = −0.21 e Å⁻³
546 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	0.75620 (12)	1.12665 (8)	0.24000 (5)	0.0463 (3)
O2	0.14926 (12)	0.65855 (8)	0.03150 (5)	0.0455 (3)
O3	0.55140 (12)	0.85168 (9)	0.25446 (5)	0.0494 (3)
O4	0.03981 (14)	0.81814 (11)	−0.11186 (6)	0.0629 (3)
O5	0.39029 (14)	0.33247 (9)	0.27240 (6)	0.0541 (3)
O6	0.39614 (13)	0.86845 (9)	0.44885 (5)	0.0511 (3)
O7	0.38552 (13)	0.58829 (10)	0.22876 (6)	0.0564 (3)
O8	0.36093 (17)	0.79742 (14)	0.60807 (6)	0.0856 (5)
C1	0.63721 (16)	1.08595 (11)	0.18260 (7)	0.0382 (3)
C2	0.58200 (17)	1.15268 (11)	0.13624 (8)	0.0423 (3)
H2	0.6302	1.2297	0.1434	0.051*
C3	0.45899 (17)	1.10584 (11)	0.08112 (7)	0.0410 (3)
H3	0.4233	1.1509	0.0496	0.049*
C4	0.38305 (16)	0.99224 (11)	0.06952 (7)	0.0364 (3)
C5	0.25120 (16)	0.94529 (11)	0.01373 (7)	0.0383 (3)
H5	0.2160	0.9910	−0.0175	0.046*
C6	0.17237 (16)	0.83613 (11)	0.00312 (7)	0.0377 (3)
C7	0.23026 (16)	0.76713 (11)	0.04875 (7)	0.0367 (3)
C8	0.35891 (15)	0.80916 (11)	0.10324 (7)	0.0357 (3)
H8	0.3957	0.7617	0.1328	0.043*
C9	0.43812 (15)	0.92381 (11)	0.11589 (7)	0.0340 (3)
C10	0.57067 (15)	0.97328 (11)	0.17229 (7)	0.0350 (3)
C11	0.63953 (16)	0.90486 (11)	0.22145 (7)	0.0354 (3)
C12	0.81623 (15)	0.89971 (10)	0.22638 (7)	0.0342 (3)
C13	0.91210 (17)	0.94624 (12)	0.18213 (7)	0.0419 (3)
H13	0.8666	0.9849	0.1486	0.050*
C14	1.07400 (18)	0.93639 (14)	0.18677 (8)	0.0505 (4)
H14	1.1390	0.9682	0.1563	0.061*
C15	1.14103 (18)	0.88071 (14)	0.23533 (8)	0.0519 (4)
H15	1.2518	0.8736	0.2382	0.062*
C16	1.04694 (18)	0.83527 (14)	0.27983 (9)	0.0526 (4)
H16	1.0936	0.7976	0.3137	0.063*
C17	0.88488 (17)	0.84427 (12)	0.27543 (8)	0.0437 (3)
H17	0.8205	0.8124	0.3061	0.052*
C18	0.02760 (17)	0.79442 (12)	−0.05542 (7)	0.0414 (3)
C19	−0.13454 (16)	0.73366 (10)	−0.04292 (7)	0.0376 (3)
C20	−0.17214 (18)	0.73856 (12)	0.02197 (8)	0.0448 (3)
H20	−0.0896	0.7760	0.0606	0.054*
C21	−0.3297 (2)	0.68907 (14)	0.03039 (10)	0.0581 (4)
H21	−0.3558	0.6935	0.0747	0.070*
C22	−0.4493 (2)	0.63315 (14)	−0.02576 (11)	0.0633 (5)
H22	−0.5573	0.5988	−0.0199	0.076*
C23	−0.4121 (2)	0.62724 (12)	−0.08983 (11)	0.0590 (5)
H23	−0.4945	0.5884	−0.1282	0.071*
C24	−0.25615 (18)	0.67716 (11)	−0.09900 (8)	0.0464 (4)
H24	−0.2316	0.6730	−0.1436	0.056*
C25	0.8244 (2)	1.24308 (12)	0.25537 (9)	0.0547 (4)
H25A	0.9051	1.2604	0.2987	0.066*
H25B	0.7351	1.2804	0.2592	0.066*
H25C	0.8798	1.2682	0.2187	0.066*
C26	0.1872 (2)	0.58516 (12)	0.07768 (9)	0.0529 (4)
H26A	0.3027	0.5808	0.0801	0.064*
H26B	0.1132	0.5118	0.0614	0.064*
H26C	0.1718	0.6124	0.1232	0.064*
C27	0.36484 (18)	0.39304 (13)	0.32852 (8)	0.0460 (3)
C28	0.3038 (2)	0.34626 (14)	0.38244 (9)	0.0543 (4)
H28	0.2800	0.2688	0.3816	0.065*
C29	0.2792 (2)	0.41289 (14)	0.43577 (9)	0.0550 (4)
H29	0.2397	0.3808	0.4724	0.066*
C30	0.31049 (17)	0.52816 (13)	0.43836 (8)	0.0456 (3)
C31	0.28001 (18)	0.59751 (14)	0.49256 (8)	0.0497 (4)
H31	0.2393	0.5657	0.5291	0.060*
C32	0.30714 (17)	0.70823 (13)	0.49412 (7)	0.0456 (3)
C33	0.37117 (17)	0.75666 (13)	0.44010 (7)	0.0434 (3)
C34	0.40361 (16)	0.69303 (12)	0.38659 (7)	0.0411 (3)
H34	0.4465	0.7267	0.3511	0.049*
C35	0.37334 (16)	0.57641 (12)	0.38400 (7)	0.0401 (3)
C36	0.40236 (16)	0.50614 (12)	0.32941 (7)	0.0412 (3)
C37	0.47086 (17)	0.55206 (11)	0.27136 (7)	0.0400 (3)
C38	0.64577 (17)	0.55189 (11)	0.26701 (7)	0.0406 (3)
C39	0.75209 (19)	0.52482 (14)	0.31930 (9)	0.0535 (4)
H39	0.7149	0.5068	0.3598	0.064*
C40	0.9143 (2)	0.52407 (15)	0.31253 (11)	0.0673 (5)
H40	0.9881	0.5068	0.3487	0.081*
C41	0.9670 (2)	0.54832 (16)	0.25342 (12)	0.0731 (6)
H41	1.0764	0.5462	0.2484	0.088*
C42	0.8617 (2)	0.57558 (17)	0.20157 (11)	0.0698 (5)
H42	0.8984	0.5921	0.1608	0.084*
C43	0.70313 (19)	0.57898 (13)	0.20861 (8)	0.0517 (4)
H43	0.6322	0.6001	0.1731	0.062*
C44	0.26992 (19)	0.77897 (14)	0.55201 (8)	0.0515 (4)
C45	0.11741 (17)	0.82003 (12)	0.54022 (7)	0.0426 (3)
C46	0.00223 (18)	0.78735 (12)	0.47869 (8)	0.0456 (3)
H46	0.0234	0.7406	0.4425	0.055*
C47	−0.1424 (2)	0.82298 (14)	0.47039 (9)	0.0545 (4)
H47	−0.2213	0.8000	0.4286	0.065*
C48	−0.1730 (2)	0.89198 (14)	0.52258 (9)	0.0570 (4)
H48	−0.2727	0.9164	0.5166	0.068*
C49	−0.0592 (2)	0.92543 (13)	0.58321 (9)	0.0542 (4)
H49	−0.0804	0.9732	0.6189	0.065*
C50	0.08573 (19)	0.88984 (12)	0.59252 (8)	0.0479 (4)
H50	0.1637	0.9129	0.6345	0.057*
C51	0.3316 (2)	0.21502 (13)	0.26385 (9)	0.0578 (4)
H51A	0.3462	0.1827	0.2193	0.069*
H51B	0.2136	0.1959	0.2661	0.069*
H51C	0.3947	0.1862	0.3003	0.069*
C52	0.46383 (19)	0.92637 (13)	0.39871 (8)	0.0499 (4)
H52A	0.4778	1.0056	0.4119	0.060*
H52B	0.3883	0.9019	0.3542	0.060*
H52C	0.5718	0.9114	0.3956	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0494 (6)	0.0427 (5)	0.0421 (6)	0.0103 (4)	0.0006 (5)	0.0016 (4)
O2	0.0443 (5)	0.0388 (5)	0.0503 (6)	0.0099 (4)	−0.0024 (5)	0.0124 (4)
O3	0.0365 (5)	0.0686 (7)	0.0494 (6)	0.0138 (5)	0.0130 (5)	0.0271 (5)
O4	0.0529 (7)	0.0952 (9)	0.0393 (6)	0.0091 (6)	0.0066 (5)	0.0267 (6)
O5	0.0627 (7)	0.0495 (6)	0.0495 (7)	0.0096 (5)	0.0141 (5)	0.0088 (5)
O6	0.0549 (6)	0.0536 (6)	0.0465 (6)	0.0110 (5)	0.0171 (5)	0.0081 (5)
O7	0.0478 (6)	0.0831 (8)	0.0468 (6)	0.0245 (6)	0.0108 (5)	0.0267 (6)
O8	0.0697 (8)	0.1516 (14)	0.0404 (7)	0.0559 (9)	−0.0025 (6)	−0.0036 (8)
C1	0.0345 (7)	0.0443 (7)	0.0382 (8)	0.0135 (6)	0.0092 (6)	0.0056 (6)
C2	0.0421 (8)	0.0378 (7)	0.0488 (9)	0.0120 (6)	0.0101 (6)	0.0082 (6)
C3	0.0403 (7)	0.0419 (7)	0.0466 (8)	0.0165 (6)	0.0105 (6)	0.0159 (6)
C4	0.0330 (7)	0.0430 (7)	0.0385 (7)	0.0145 (5)	0.0116 (6)	0.0122 (6)
C5	0.0360 (7)	0.0466 (7)	0.0379 (8)	0.0156 (6)	0.0092 (6)	0.0167 (6)
C6	0.0325 (7)	0.0474 (7)	0.0360 (7)	0.0126 (6)	0.0074 (6)	0.0120 (6)
C7	0.0324 (7)	0.0404 (7)	0.0398 (8)	0.0112 (5)	0.0082 (6)	0.0105 (6)
C8	0.0326 (7)	0.0414 (7)	0.0386 (7)	0.0153 (5)	0.0086 (6)	0.0136 (6)
C9	0.0293 (6)	0.0419 (7)	0.0362 (7)	0.0143 (5)	0.0114 (5)	0.0095 (6)
C10	0.0309 (6)	0.0425 (7)	0.0358 (7)	0.0143 (5)	0.0096 (5)	0.0086 (6)
C11	0.0329 (7)	0.0412 (7)	0.0324 (7)	0.0090 (5)	0.0071 (5)	0.0062 (6)
C12	0.0312 (7)	0.0370 (6)	0.0328 (7)	0.0086 (5)	0.0028 (5)	0.0029 (5)
C13	0.0374 (7)	0.0555 (8)	0.0363 (8)	0.0154 (6)	0.0089 (6)	0.0105 (6)
C14	0.0375 (8)	0.0733 (10)	0.0430 (9)	0.0149 (7)	0.0130 (6)	0.0079 (7)
C15	0.0335 (7)	0.0730 (11)	0.0485 (9)	0.0193 (7)	0.0032 (7)	0.0011 (8)
C16	0.0420 (8)	0.0635 (10)	0.0531 (10)	0.0208 (7)	−0.0020 (7)	0.0143 (8)
C17	0.0378 (7)	0.0485 (8)	0.0452 (8)	0.0103 (6)	0.0051 (6)	0.0138 (6)
C18	0.0410 (8)	0.0491 (8)	0.0367 (8)	0.0145 (6)	0.0062 (6)	0.0122 (6)
C19	0.0382 (7)	0.0366 (7)	0.0393 (8)	0.0131 (5)	0.0028 (6)	0.0108 (6)
C20	0.0411 (8)	0.0520 (8)	0.0445 (8)	0.0149 (6)	0.0061 (6)	0.0169 (7)
C21	0.0502 (9)	0.0697 (11)	0.0676 (11)	0.0217 (8)	0.0212 (8)	0.0374 (9)
C22	0.0401 (9)	0.0490 (9)	0.1035 (16)	0.0077 (7)	0.0110 (9)	0.0343 (10)
C23	0.0454 (9)	0.0394 (8)	0.0824 (13)	0.0080 (7)	−0.0092 (9)	0.0054 (8)
C24	0.0477 (8)	0.0403 (7)	0.0487 (9)	0.0159 (6)	−0.0034 (7)	0.0046 (6)
C25	0.0589 (10)	0.0460 (8)	0.0514 (10)	0.0046 (7)	0.0043 (8)	0.0009 (7)
C26	0.0506 (9)	0.0443 (8)	0.0618 (10)	0.0093 (7)	0.0004 (8)	0.0204 (7)
C27	0.0418 (8)	0.0532 (8)	0.0427 (8)	0.0097 (6)	0.0074 (6)	0.0120 (7)
C28	0.0579 (10)	0.0518 (9)	0.0534 (10)	0.0073 (7)	0.0128 (8)	0.0182 (8)
C29	0.0557 (9)	0.0646 (10)	0.0486 (10)	0.0096 (8)	0.0173 (8)	0.0255 (8)
C30	0.0396 (8)	0.0593 (9)	0.0396 (8)	0.0099 (6)	0.0090 (6)	0.0168 (7)
C31	0.0450 (8)	0.0716 (10)	0.0359 (8)	0.0125 (7)	0.0127 (6)	0.0192 (7)
C32	0.0381 (7)	0.0643 (9)	0.0355 (8)	0.0134 (7)	0.0068 (6)	0.0112 (7)
C33	0.0337 (7)	0.0566 (9)	0.0385 (8)	0.0082 (6)	0.0051 (6)	0.0106 (7)
C34	0.0327 (7)	0.0549 (8)	0.0359 (8)	0.0073 (6)	0.0082 (6)	0.0124 (6)
C35	0.0298 (7)	0.0551 (8)	0.0350 (7)	0.0077 (6)	0.0048 (5)	0.0128 (6)
C36	0.0337 (7)	0.0517 (8)	0.0377 (8)	0.0085 (6)	0.0053 (6)	0.0115 (6)
C37	0.0364 (7)	0.0461 (7)	0.0357 (8)	0.0082 (6)	0.0043 (6)	0.0066 (6)
C38	0.0364 (7)	0.0409 (7)	0.0412 (8)	0.0047 (6)	0.0066 (6)	0.0036 (6)
C39	0.0413 (8)	0.0607 (9)	0.0565 (10)	0.0108 (7)	0.0040 (7)	0.0125 (8)
C40	0.0405 (9)	0.0676 (11)	0.0880 (14)	0.0139 (8)	−0.0037 (9)	0.0113 (10)
C41	0.0414 (9)	0.0769 (12)	0.1002 (16)	0.0101 (8)	0.0242 (10)	0.0030 (11)
C42	0.0481 (10)	0.0860 (13)	0.0727 (13)	0.0028 (9)	0.0272 (9)	0.0055 (10)
C43	0.0436 (8)	0.0582 (9)	0.0490 (9)	0.0013 (7)	0.0127 (7)	0.0065 (7)
C44	0.0449 (8)	0.0732 (11)	0.0368 (8)	0.0136 (7)	0.0083 (7)	0.0110 (7)
C45	0.0408 (7)	0.0479 (8)	0.0387 (8)	0.0051 (6)	0.0105 (6)	0.0134 (6)
C46	0.0453 (8)	0.0500 (8)	0.0409 (8)	0.0084 (6)	0.0085 (6)	0.0110 (6)
C47	0.0481 (9)	0.0646 (10)	0.0484 (9)	0.0128 (7)	0.0010 (7)	0.0140 (8)
C48	0.0516 (9)	0.0609 (10)	0.0642 (11)	0.0210 (8)	0.0129 (8)	0.0171 (8)
C49	0.0586 (10)	0.0486 (9)	0.0582 (10)	0.0137 (7)	0.0181 (8)	0.0089 (7)
C50	0.0474 (8)	0.0506 (8)	0.0424 (8)	0.0039 (7)	0.0095 (7)	0.0085 (7)
C51	0.0624 (10)	0.0501 (9)	0.0607 (11)	0.0146 (8)	0.0095 (8)	0.0107 (8)
C52	0.0500 (9)	0.0558 (9)	0.0451 (9)	0.0117 (7)	0.0106 (7)	0.0135 (7)

Geometric parameters (Å, º) top

O1—C1	1.3606 (16)	C25—H25A	0.9800
O1—C25	1.4306 (17)	C25—H25B	0.9800
O2—C7	1.3647 (16)	C25—H25C	0.9800
O2—C26	1.4251 (17)	C26—H26A	0.9800
O3—C11	1.2172 (16)	C26—H26B	0.9800
O4—C18	1.2168 (17)	C26—H26C	0.9800
O5—C27	1.3646 (18)	C27—C36	1.387 (2)
O5—C51	1.4340 (18)	C27—C28	1.405 (2)
O6—C33	1.3641 (18)	C28—C29	1.360 (2)
O6—C52	1.4276 (18)	C28—H28	0.9500
O7—C37	1.2157 (17)	C29—C30	1.411 (2)
O8—C44	1.2170 (18)	C29—H29	0.9500
C1—C10	1.3848 (19)	C30—C31	1.414 (2)
C1—C2	1.408 (2)	C30—C35	1.426 (2)
C2—C3	1.360 (2)	C31—C32	1.359 (2)
C2—H2	0.9500	C31—H31	0.9500
C3—C4	1.4090 (19)	C32—C33	1.426 (2)
C3—H3	0.9500	C32—C44	1.504 (2)
C4—C5	1.4090 (19)	C33—C34	1.370 (2)
C4—C9	1.4242 (18)	C34—C35	1.428 (2)
C5—C6	1.3652 (19)	C34—H34	0.9500
C5—H5	0.9500	C35—C36	1.420 (2)
C6—C7	1.4282 (19)	C36—C37	1.500 (2)
C6—C18	1.4984 (18)	C37—C38	1.4918 (19)
C7—C8	1.3687 (18)	C38—C39	1.384 (2)
C8—C9	1.4261 (18)	C38—C43	1.388 (2)
C8—H8	0.9500	C39—C40	1.399 (2)
C9—C10	1.4252 (18)	C39—H39	0.9500
C10—C11	1.5045 (19)	C40—C41	1.376 (3)
C11—C12	1.4921 (18)	C40—H40	0.9500
C12—C17	1.3875 (19)	C41—C42	1.374 (3)
C12—C13	1.3892 (19)	C41—H41	0.9500
C13—C14	1.386 (2)	C42—C43	1.377 (2)
C13—H13	0.9500	C42—H42	0.9500
C14—C15	1.377 (2)	C43—H43	0.9500
C14—H14	0.9500	C44—C45	1.481 (2)
C15—C16	1.379 (2)	C45—C50	1.394 (2)
C15—H15	0.9500	C45—C46	1.395 (2)
C16—C17	1.384 (2)	C46—C47	1.380 (2)
C16—H16	0.9500	C46—H46	0.9500
C17—H17	0.9500	C47—C48	1.382 (2)
C18—C19	1.4872 (19)	C47—H47	0.9500
C19—C20	1.389 (2)	C48—C49	1.377 (2)
C19—C24	1.3927 (19)	C48—H48	0.9500
C20—C21	1.384 (2)	C49—C50	1.382 (2)
C20—H20	0.9500	C49—H49	0.9500
C21—C22	1.384 (3)	C50—H50	0.9500
C21—H21	0.9500	C51—H51A	0.9800
C22—C23	1.371 (3)	C51—H51B	0.9800
C22—H22	0.9500	C51—H51C	0.9800
C23—C24	1.378 (2)	C52—H52A	0.9800
C23—H23	0.9500	C52—H52B	0.9800
C24—H24	0.9500	C52—H52C	0.9800

C1—O1—C25	118.57 (11)	H26A—C26—H26C	109.5
C7—O2—C26	117.91 (11)	H26B—C26—H26C	109.5
C27—O5—C51	118.04 (12)	O5—C27—C36	115.63 (13)
C33—O6—C52	118.14 (11)	O5—C27—C28	123.42 (14)
O1—C1—C10	115.76 (12)	C36—C27—C28	120.96 (14)
O1—C1—C2	123.07 (12)	C29—C28—C27	119.40 (15)
C10—C1—C2	121.16 (13)	C29—C28—H28	120.3
C3—C2—C1	119.35 (13)	C27—C28—H28	120.3
C3—C2—H2	120.3	C28—C29—C30	122.05 (15)
C1—C2—H2	120.3	C28—C29—H29	119.0
C2—C3—C4	121.78 (13)	C30—C29—H29	119.0
C2—C3—H3	119.1	C29—C30—C31	122.31 (14)
C4—C3—H3	119.1	C29—C30—C35	118.90 (14)
C5—C4—C3	121.30 (12)	C31—C30—C35	118.78 (14)
C5—C4—C9	119.27 (12)	C32—C31—C30	122.09 (14)
C3—C4—C9	119.41 (12)	C32—C31—H31	119.0
C6—C5—C4	122.06 (12)	C30—C31—H31	119.0
C6—C5—H5	119.0	C31—C32—C33	119.19 (14)
C4—C5—H5	119.0	C31—C32—C44	120.49 (14)
C5—C6—C7	118.58 (12)	C33—C32—C44	120.32 (14)
C5—C6—C18	118.45 (12)	O6—C33—C34	125.97 (13)
C7—C6—C18	122.97 (12)	O6—C33—C32	113.10 (13)
O2—C7—C8	124.78 (12)	C34—C33—C32	120.93 (14)
O2—C7—C6	113.96 (11)	C33—C34—C35	120.31 (13)
C8—C7—C6	121.23 (12)	C33—C34—H34	119.8
C7—C8—C9	120.42 (12)	C35—C34—H34	119.8
C7—C8—H8	119.8	C36—C35—C30	118.47 (13)
C9—C8—H8	119.8	C36—C35—C34	122.84 (13)
C4—C9—C10	118.28 (12)	C30—C35—C34	118.69 (13)
C4—C9—C8	118.39 (12)	C27—C36—C35	120.16 (13)
C10—C9—C8	123.33 (12)	C27—C36—C37	118.84 (13)
C1—C10—C9	119.93 (12)	C35—C36—C37	120.99 (13)
C1—C10—C11	119.13 (12)	O7—C37—C38	120.84 (13)
C9—C10—C11	120.94 (12)	O7—C37—C36	120.69 (13)
O3—C11—C12	120.80 (12)	C38—C37—C36	118.47 (12)
O3—C11—C10	120.73 (12)	C39—C38—C43	119.07 (14)
C12—C11—C10	118.42 (11)	C39—C38—C37	121.92 (14)
C17—C12—C13	119.27 (12)	C43—C38—C37	119.01 (13)
C17—C12—C11	118.88 (12)	C38—C39—C40	119.94 (17)
C13—C12—C11	121.83 (12)	C38—C39—H39	120.0
C14—C13—C12	120.13 (14)	C40—C39—H39	120.0
C14—C13—H13	119.9	C41—C40—C39	119.94 (18)
C12—C13—H13	119.9	C41—C40—H40	120.0
C15—C14—C13	120.28 (15)	C39—C40—H40	120.0
C15—C14—H14	119.9	C42—C41—C40	120.14 (16)
C13—C14—H14	119.9	C42—C41—H41	119.9
C14—C15—C16	119.83 (14)	C40—C41—H41	119.9
C14—C15—H15	120.1	C41—C42—C43	120.15 (18)
C16—C15—H15	120.1	C41—C42—H42	119.9
C15—C16—C17	120.33 (14)	C43—C42—H42	119.9
C15—C16—H16	119.8	C42—C43—C38	120.70 (17)
C17—C16—H16	119.8	C42—C43—H43	119.6
C16—C17—C12	120.16 (14)	C38—C43—H43	119.6
C16—C17—H17	119.9	O8—C44—C45	121.31 (15)
C12—C17—H17	119.9	O8—C44—C32	119.79 (15)
O4—C18—C19	120.28 (13)	C45—C44—C32	118.83 (13)
O4—C18—C6	119.60 (13)	C50—C45—C46	119.36 (14)
C19—C18—C6	119.86 (12)	C50—C45—C44	119.28 (14)
C20—C19—C24	119.30 (14)	C46—C45—C44	121.32 (14)
C20—C19—C18	122.06 (12)	C47—C46—C45	119.98 (15)
C24—C19—C18	118.46 (13)	C47—C46—H46	120.0
C21—C20—C19	120.10 (15)	C45—C46—H46	120.0
C21—C20—H20	120.0	C46—C47—C48	120.27 (15)
C19—C20—H20	120.0	C46—C47—H47	119.9
C22—C21—C20	119.99 (17)	C48—C47—H47	119.9
C22—C21—H21	120.0	C49—C48—C47	120.08 (15)
C20—C21—H21	120.0	C49—C48—H48	120.0
C23—C22—C21	120.04 (16)	C47—C48—H48	120.0
C23—C22—H22	120.0	C48—C49—C50	120.36 (15)
C21—C22—H22	120.0	C48—C49—H49	119.8
C22—C23—C24	120.54 (16)	C50—C49—H49	119.8
C22—C23—H23	119.7	C49—C50—C45	119.94 (15)
C24—C23—H23	119.7	C49—C50—H50	120.0
C23—C24—C19	120.02 (16)	C45—C50—H50	120.0
C23—C24—H24	120.0	O5—C51—H51A	109.5
C19—C24—H24	120.0	O5—C51—H51B	109.5
O1—C25—H25A	109.5	H51A—C51—H51B	109.5
O1—C25—H25B	109.5	O5—C51—H51C	109.5
H25A—C25—H25B	109.5	H51A—C51—H51C	109.5
O1—C25—H25C	109.5	H51B—C51—H51C	109.5
H25A—C25—H25C	109.5	O6—C52—H52A	109.5
H25B—C25—H25C	109.5	O6—C52—H52B	109.5
O2—C26—H26A	109.5	H52A—C52—H52B	109.5
O2—C26—H26B	109.5	O6—C52—H52C	109.5
H26A—C26—H26B	109.5	H52A—C52—H52C	109.5
O2—C26—H26C	109.5	H52B—C52—H52C	109.5

C25—O1—C1—C10	−177.07 (12)	C51—O5—C27—C36	−171.18 (13)
C25—O1—C1—C2	2.29 (19)	C51—O5—C27—C28	8.4 (2)
O1—C1—C2—C3	−178.06 (12)	O5—C27—C28—C29	−178.70 (14)
C10—C1—C2—C3	1.3 (2)	C36—C27—C28—C29	0.9 (2)
C1—C2—C3—C4	1.0 (2)	C27—C28—C29—C30	1.1 (2)
C2—C3—C4—C5	177.43 (13)	C28—C29—C30—C31	177.89 (16)
C2—C3—C4—C9	−1.2 (2)	C28—C29—C30—C35	−1.4 (2)
C3—C4—C5—C6	−177.64 (13)	C29—C30—C31—C32	−178.62 (14)
C9—C4—C5—C6	0.99 (19)	C35—C30—C31—C32	0.7 (2)
C4—C5—C6—C7	−2.4 (2)	C30—C31—C32—C33	−1.1 (2)
C4—C5—C6—C18	176.84 (12)	C30—C31—C32—C44	178.77 (14)
C26—O2—C7—C8	7.8 (2)	C52—O6—C33—C34	−0.7 (2)
C26—O2—C7—C6	−173.92 (13)	C52—O6—C33—C32	178.53 (12)
C5—C6—C7—O2	−176.53 (12)	C31—C32—C33—O6	−178.54 (12)
C18—C6—C7—O2	4.24 (18)	C44—C32—C33—O6	1.55 (19)
C5—C6—C7—C8	1.8 (2)	C31—C32—C33—C34	0.8 (2)
C18—C6—C7—C8	−177.42 (12)	C44—C32—C33—C34	−179.15 (13)
O2—C7—C8—C9	178.41 (12)	O6—C33—C34—C35	179.31 (12)
C6—C7—C8—C9	0.26 (19)	C32—C33—C34—C35	0.1 (2)
C5—C4—C9—C10	−179.44 (11)	C29—C30—C35—C36	−0.2 (2)
C3—C4—C9—C10	−0.78 (18)	C31—C30—C35—C36	−179.48 (13)
C5—C4—C9—C8	1.10 (18)	C29—C30—C35—C34	179.53 (13)
C3—C4—C9—C8	179.75 (12)	C31—C30—C35—C34	0.2 (2)
C7—C8—C9—C4	−1.69 (18)	C33—C34—C35—C36	179.10 (13)
C7—C8—C9—C10	178.87 (12)	C33—C34—C35—C30	−0.6 (2)
O1—C1—C10—C9	176.13 (11)	O5—C27—C36—C35	177.17 (12)
C2—C1—C10—C9	−3.24 (19)	C28—C27—C36—C35	−2.4 (2)
O1—C1—C10—C11	−3.54 (17)	O5—C27—C36—C37	−1.77 (19)
C2—C1—C10—C11	177.08 (12)	C28—C27—C36—C37	178.60 (14)
C4—C9—C10—C1	2.95 (18)	C30—C35—C36—C27	2.1 (2)
C8—C9—C10—C1	−177.61 (12)	C34—C35—C36—C27	−177.65 (13)
C4—C9—C10—C11	−177.38 (11)	C30—C35—C36—C37	−179.02 (12)
C8—C9—C10—C11	2.06 (19)	C34—C35—C36—C37	1.3 (2)
C1—C10—C11—O3	119.31 (15)	C27—C36—C37—O7	106.69 (17)
C9—C10—C11—O3	−60.36 (18)	C35—C36—C37—O7	−72.25 (19)
C1—C10—C11—C12	−63.44 (16)	C27—C36—C37—C38	−73.11 (17)
C9—C10—C11—C12	116.89 (13)	C35—C36—C37—C38	107.95 (15)
O3—C11—C12—C17	−7.9 (2)	O7—C37—C38—C39	171.32 (14)
C10—C11—C12—C17	174.81 (12)	C36—C37—C38—C39	−8.9 (2)
O3—C11—C12—C13	170.31 (13)	O7—C37—C38—C43	−9.1 (2)
C10—C11—C12—C13	−6.93 (19)	C36—C37—C38—C43	170.69 (13)
C17—C12—C13—C14	0.5 (2)	C43—C38—C39—C40	−0.6 (2)
C11—C12—C13—C14	−177.72 (13)	C37—C38—C39—C40	178.99 (14)
C12—C13—C14—C15	−0.2 (2)	C38—C39—C40—C41	−1.2 (3)
C13—C14—C15—C16	−0.5 (2)	C39—C40—C41—C42	1.4 (3)
C14—C15—C16—C17	0.7 (2)	C40—C41—C42—C43	0.1 (3)
C15—C16—C17—C12	−0.4 (2)	C41—C42—C43—C38	−1.9 (3)
C13—C12—C17—C16	−0.3 (2)	C39—C38—C43—C42	2.1 (2)
C11—C12—C17—C16	178.04 (13)	C37—C38—C43—C42	−177.46 (15)
C5—C6—C18—O4	48.67 (19)	C31—C32—C44—O8	73.7 (2)
C7—C6—C18—O4	−132.11 (15)	C33—C32—C44—O8	−106.41 (19)
C5—C6—C18—C19	−125.45 (14)	C31—C32—C44—C45	−103.19 (17)
C7—C6—C18—C19	53.78 (18)	C33—C32—C44—C45	76.72 (19)
O4—C18—C19—C20	−156.43 (15)	O8—C44—C45—C50	6.2 (2)
C6—C18—C19—C20	17.6 (2)	C32—C44—C45—C50	−177.02 (14)
O4—C18—C19—C24	18.6 (2)	O8—C44—C45—C46	−171.66 (17)
C6—C18—C19—C24	−167.32 (12)	C32—C44—C45—C46	5.2 (2)
C24—C19—C20—C21	−1.0 (2)	C50—C45—C46—C47	−0.8 (2)
C18—C19—C20—C21	174.04 (13)	C44—C45—C46—C47	177.00 (14)
C19—C20—C21—C22	1.0 (2)	C45—C46—C47—C48	0.7 (2)
C20—C21—C22—C23	−0.3 (2)	C46—C47—C48—C49	−0.1 (3)
C21—C22—C23—C24	−0.3 (2)	C47—C48—C49—C50	−0.4 (2)
C22—C23—C24—C19	0.4 (2)	C48—C49—C50—C45	0.2 (2)
C20—C19—C24—C23	0.3 (2)	C46—C45—C50—C49	0.4 (2)
C18—C19—C24—C23	−174.90 (13)	C44—C45—C50—C49	−177.50 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C19–C24 and C4–C9 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O3ⁱ	0.95	2.57	3.5191 (19)	176
C25—H25C···O4ⁱⁱ	0.98	2.56	3.348 (2)	138
C51—H51C···O8ⁱⁱⁱ	0.98	2.47	3.371 (2)	152
C3—H3···Cg1^iv	0.95	2.59	3.416 (11)	145
C14—H14···Cg2^v	0.95	2.86	3.578 (9)	133

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+2, −z; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+2, −z; (v) x−1, y, 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)	8.42828 (15), 12.5953 (2), 20.0578 (4)
α, β, γ (°)	96.222 (1), 99.688 (1), 102.727 (1)
V (Å³)	2023.76 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.60 × 0.40 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.677, 0.933
No. of measured, independent and observed [I > 2σ(I)] reflections	32431, 7263, 5957
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.115, 1.08
No. of reflections	7263
No. of parameters	546
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.21

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku, 2010), IL MILIONE (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).