(2,7-Dimeth­oxy­naphthalen-1-yl)(4-meth­oxy­phen­yl)methanone

Sasagawa, K.; Sakamoto, R.; Hijikata, D.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536813003218

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o363

doi:10.1107/S1600536813003218

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(2,7-Dimethoxynaphthalen-1-yl)(4-methoxyphenyl)methanone

Kosuke Sasagawa,^a Rei Sakamoto,^a Daichi Hijikata,^a Akiko Okamoto ^a ^* and Noriyuki Yonezawa ^a

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

(Received 30 January 2013; accepted 31 January 2013; online 9 February 2013)

In the molecule of the title compound, C₂₀H₁₈O₄, the dihedral angle between the naphthalene ring system and the benzene ring is 81.74 (5)°. An intermolecular C—H⋯O interaction is formed between an H atom at the 6-position of the naphthalene ring and the O atom of the methoxy group at the 7-position.

Related literature

For formation reactions of aroylated naphthalene compounds via electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ); Okamoto et al. (2011 ). For the structures of closely related compounds, see: Nakaema et al. (2008 ); Hijikata et al. (2010 ); Kato et al. (2010 ); Tsumuki et al. (2011 , 2012 ).

Experimental

Crystal data

C₂₀H₁₈O₄
M_r = 322.34
Monoclinic, P 2₁ /c
a = 14.9638 (2) Å
b = 7.9191 (1) Å
c = 13.6394 (2) Å
β = 92.56°
V = 1614.64 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.75 mm⁻¹
T = 193 K
0.60 × 0.40 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.662, T_max = 0.806
27665 measured reflections
2957 independent reflections
2701 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.106
S = 1.05
2957 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3ⁱ	0.95	2.51	3.4592 (16)	178
Symmetry code: (i) -x, -y, -z.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813003218/pk2464sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813003218/pk2464Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813003218/pk2464Isup3.cml

checkCIF report

Comment top

In the course of our study on selective electrophilic aromatic aroylation of the naphthalene ring core, 1-aroylnaphthalene and 1,8-diaroylnaphthalene compounds have proved to be formed regioselectively by the aid of a suitable acidic mediator (Okamoto & Yonezawa, 2009, Okamoto et al., 2011). Recently, we have reported the X-ray crystal structures of 1,8-diaroylated 2,7-dimethoxynaphthalene derivatives such as 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008) and [2,7-dimethoxy-8-(2-naphthoyl)-naphthalen-1-yl](naphthalen-2-yl)-methanone [1,8-bis(2-naphthoyl)-2,7-dimethoxynaphthalene] (Tsumuki et al., 2011). The aroyl groups in the 1,8-diaroylnaphthalene compounds are almost perpendicular to the naphthalene rings and oriented in opposite directions (anti-orientation). On the other hand, we have also clarified the minor structure of the 1,8-diaroylnaphthalene derivatives, which the two aroyl groups are oriented in same direction (syn-orientation), [2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene; Hijikata et al., 2010]. Moreover, we have reported crystal structures of 1-aroylnapthalene compounds such as (2,7-dimethoxynaphthalen-1-yl)-(phenyl)methanone (1-benzoyl-2,7-dimethoxynaphthalene) (Kato et al., 2010) and 2,7-dimethoxy-1-(2-naphthoyl)naphthalene (Tsumuki et al., 2012). They have essentially same non-coplanar structure as the homologous 1,8-diaroylnaphthalenes.

As a part of our ongoing studies on the molecular structures of these kinds of homologous molecules, the X-ray crystal structure of the title compound, 1-aroylated naphthalene bearing methoxy groups on aroyl group, is discussed in this article.

The molecular structure of the title compound is displayed in Fig. 1. The dihedral angle between the best planes of the phenyl ring and the naphthalene ring is 81.74 (5) °.

The dihedral angle between the naphthalene ring system and the bridging ketonic carbonyl C—C(=O)—C plane is larger than that between the phenyl ring and the bridging carbonyl plane [74.77 (6)° versus. 13.27 (6) °].

In the molecular packing, C—H···O interactions between the aromatic hydrogen atoms at the 6-position of the naphthalene ring and the methoxy oxygen atoms at the 7-position are observed (C5—H5···O3 = 2.51 Å; symmetry code: -x, -y, -z; Fig. 2). Moreover, the naphthalene rings are aligned in parallel to each other along b axis (Fig. 3).

Related literature top

For formation reactions of aroylated naphthalene compounds via electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011). For the structures of closely related compounds, see: Nakaema et al. (2008); Hijikata et al. (2010); Kato et al. (2010); Tsumuki et al. (2011, 2012).

Experimental top

4-Methoxybenzoyl chloride (11.0 mmol, 1.96 g), aluminium chloride (11.0 mmol, 1.47 g) and methylene chloride (25.0 ml) were placed into a 100 ml flask, followed by stirring at 273 K. To the reaction mixture thus obtained, 2,7-dimethoxynaphthalene (10.0 mmol, 1.88 g) was added. The reaction mixture was poured into ice-cold water (100 ml) after it had been stirred for 6 h at 273 K. The aqueous layer was extracted with CHCl₃ (20 ml × 3). The combined extracts were washed with 2M aqueous NaOH followed by washing with brine. The extracts thus obtained were dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give a cake. The crude product was purified by recrystallization from methanol (yield 44%). Colorless platelet single crystals suitable for X-ray diffraction were obtained by repeated crystallization from methanol.

Spectroscopic Data:

¹H NMR δ (300 MHz, CDCl₃): 3.70 (3H, s), 3.79 (3H, s), 3.83 (3H, s), 6.78 (1H, d, J = 2.4 Hz), 6.89 (2H, d, J = 9.0 Hz), 7.00 (1H, dd, J = 9.0, 2.4 Hz), 7.15 (1H, d, J = 9.0 Hz), 7.70 (1H, d, J = 9.0 Hz), 7.83 (3H, d, J = 9.0 Hz) p.p.m. ¹³C NMR δ (75 MHz, CDCl₃): 55.14, 55.41, 56.36, 102.17, 110.28, 113.73, 116.98, 122.15, 124.34, 129.56, 130.61, 131.09, 131.98, 132.98, 154.60, 158.69, 163.81, 196.54 p.p.m. IR (KBr): 1659 (C=O), 1624, 1599, 1510 (Ar), 1251 (OMe) cm^-1 HRMS (m/z): [M+H]⁺ calcd. for C₂₀H₁₉O₄, 323.1283, found, 323.1332 m.p. = 368.5–368.9 K

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. Molecular structure with the atom-labeling scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Intermolecular C—H···O interactions between H5 and O3 [symmetry code: -x, -y, -z] along the c axis (dashed lines).
	Fig. 3. Alignment of the naphthalene rings along b axis.

(2,7-Dimethoxynaphthalen-1-yl)(4-methoxyphenyl)methanone top

Crystal data top

C₂₀H₁₈O₄	F(000) = 680
M_r = 322.34	D_x = 1.326 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 25377 reflections
a = 14.9638 (2) Å	θ = 3.0–68.2°
b = 7.9191 (1) Å	µ = 0.75 mm⁻¹
c = 13.6394 (2) Å	T = 193 K
β = 92.56°	Block, colorless
V = 1614.64 (4) Å³	0.60 × 0.40 × 0.30 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	2957 independent reflections
Radiation source: fine-focus sealed tube	2701 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 10.000 pixels mm^-1	θ_max = 68.2°, θ_min = 3.0°
ω scans	h = −17→18
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −9→9
T_min = 0.662, T_max = 0.806	l = −16→16
27665 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)] = 0.038	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0622P)² + 0.323P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2957 reflections	Δρ_max = 0.24 e Å⁻³
221 parameters	Δρ_min = −0.18 e Å⁻³
0 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: 0.0093 (6)

Crystal data top

C₂₀H₁₈O₄	V = 1614.64 (4) Å³
M_r = 322.34	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 14.9638 (2) Å	µ = 0.75 mm⁻¹
b = 7.9191 (1) Å	T = 193 K
c = 13.6394 (2) Å	0.60 × 0.40 × 0.30 mm
β = 92.56°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2957 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2701 reflections with I > 2σ(I)
T_min = 0.662, T_max = 0.806	R_int = 0.051
27665 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.05	Δρ_max = 0.24 e Å⁻³
2957 reflections	Δρ_min = −0.18 e Å⁻³
221 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	0.34025 (6)	−0.17441 (11)	0.36039 (7)	0.0431 (3)
O2	0.26300 (6)	0.04715 (12)	0.55470 (6)	0.0428 (3)
O3	0.12880 (6)	−0.05902 (13)	0.04035 (7)	0.0463 (3)
O4	0.58557 (5)	0.47580 (11)	0.37408 (7)	0.0392 (2)
C1	0.22392 (8)	0.02329 (15)	0.38741 (9)	0.0324 (3)
C2	0.19845 (8)	0.06572 (15)	0.48029 (9)	0.0355 (3)
C3	0.11163 (8)	0.12450 (17)	0.49646 (10)	0.0403 (3)
H3	0.0950	0.1532	0.5608	0.048*
C4	0.05162 (8)	0.13973 (17)	0.41872 (10)	0.0412 (3)
H4	−0.0063	0.1833	0.4294	0.049*
C5	0.01000 (8)	0.10274 (18)	0.24246 (10)	0.0423 (3)
H5	−0.0480	0.1466	0.2526	0.051*
C6	0.03049 (8)	0.05121 (18)	0.15138 (10)	0.0430 (3)
H6	−0.0132	0.0565	0.0988	0.052*
C7	0.11745 (8)	−0.01061 (17)	0.13501 (9)	0.0373 (3)
C8	0.18197 (8)	−0.01881 (15)	0.20971 (9)	0.0342 (3)
H8	0.2404	−0.0578	0.1970	0.041*
C9	0.16091 (8)	0.03151 (15)	0.30639 (9)	0.0325 (3)
C10	0.07321 (8)	0.09269 (16)	0.32321 (9)	0.0364 (3)
C11	0.31989 (8)	−0.02724 (15)	0.37353 (8)	0.0318 (3)
C12	0.38717 (7)	0.11016 (15)	0.37531 (8)	0.0294 (3)
C13	0.36306 (7)	0.28000 (15)	0.36920 (8)	0.0311 (3)
H13	0.3015	0.3094	0.3664	0.037*
C14	0.42667 (8)	0.40714 (15)	0.36708 (8)	0.0317 (3)
H14	0.4090	0.5221	0.3614	0.038*
C15	0.51697 (7)	0.36349 (15)	0.37345 (8)	0.0311 (3)
C16	0.54233 (7)	0.19433 (16)	0.38133 (9)	0.0348 (3)
H16	0.6039	0.1652	0.3868	0.042*
C17	0.47838 (8)	0.06988 (15)	0.38119 (9)	0.0333 (3)
H17	0.4963	−0.0451	0.3851	0.040*
C18	0.23465 (11)	0.0506 (2)	0.65301 (10)	0.0510 (4)
H18A	0.1872	−0.0331	0.6605	0.061*
H18B	0.2118	0.1633	0.6679	0.061*
H18C	0.2854	0.0239	0.6982	0.061*
C19	0.21651 (9)	−0.1007 (2)	0.01257 (10)	0.0474 (3)
H19A	0.2387	−0.1976	0.0511	0.057*
H19B	0.2562	−0.0038	0.0248	0.057*
H19C	0.2151	−0.1293	−0.0574	0.057*
C20	0.56375 (9)	0.65140 (16)	0.37488 (9)	0.0381 (3)
H20A	0.6189	0.7181	0.3815	0.046*
H20B	0.5263	0.6754	0.4303	0.046*
H20C	0.5311	0.6812	0.3134	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0377 (5)	0.0318 (5)	0.0599 (6)	0.0008 (4)	0.0037 (4)	−0.0008 (4)
O2	0.0388 (5)	0.0573 (6)	0.0324 (5)	−0.0005 (4)	0.0015 (4)	−0.0039 (4)
O3	0.0376 (5)	0.0627 (6)	0.0380 (5)	0.0012 (4)	−0.0039 (4)	−0.0055 (4)
O4	0.0325 (4)	0.0321 (5)	0.0529 (5)	−0.0025 (3)	0.0004 (4)	0.0000 (4)
C1	0.0305 (6)	0.0302 (6)	0.0367 (6)	−0.0026 (5)	0.0038 (5)	0.0014 (5)
C2	0.0346 (6)	0.0349 (7)	0.0372 (6)	−0.0039 (5)	0.0023 (5)	−0.0005 (5)
C3	0.0399 (7)	0.0416 (7)	0.0403 (7)	−0.0006 (5)	0.0102 (5)	−0.0040 (5)
C4	0.0333 (6)	0.0401 (7)	0.0510 (7)	0.0027 (5)	0.0099 (5)	0.0013 (6)
C5	0.0283 (6)	0.0479 (8)	0.0506 (7)	0.0013 (5)	0.0022 (5)	0.0041 (6)
C6	0.0323 (6)	0.0517 (8)	0.0446 (7)	−0.0013 (5)	−0.0045 (5)	0.0040 (6)
C7	0.0348 (6)	0.0389 (7)	0.0380 (6)	−0.0036 (5)	−0.0003 (5)	0.0011 (5)
C8	0.0292 (6)	0.0339 (6)	0.0396 (7)	−0.0014 (5)	0.0021 (5)	0.0011 (5)
C9	0.0302 (6)	0.0288 (6)	0.0385 (6)	−0.0028 (4)	0.0028 (5)	0.0028 (5)
C10	0.0303 (6)	0.0351 (7)	0.0442 (7)	−0.0013 (5)	0.0046 (5)	0.0028 (5)
C11	0.0328 (6)	0.0345 (7)	0.0281 (6)	0.0024 (5)	0.0002 (4)	0.0020 (5)
C12	0.0306 (6)	0.0310 (6)	0.0264 (5)	0.0016 (4)	0.0009 (4)	0.0011 (4)
C13	0.0285 (5)	0.0350 (6)	0.0298 (5)	0.0042 (5)	0.0009 (4)	0.0014 (5)
C14	0.0351 (6)	0.0294 (6)	0.0306 (6)	0.0039 (5)	0.0008 (4)	0.0010 (5)
C15	0.0314 (6)	0.0329 (6)	0.0289 (5)	−0.0007 (5)	0.0008 (4)	−0.0010 (5)
C16	0.0271 (6)	0.0351 (7)	0.0419 (7)	0.0044 (5)	0.0000 (5)	0.0002 (5)
C17	0.0339 (6)	0.0294 (6)	0.0365 (6)	0.0050 (5)	0.0010 (5)	0.0015 (5)
C18	0.0548 (8)	0.0635 (10)	0.0348 (7)	0.0035 (7)	0.0044 (6)	−0.0049 (6)
C19	0.0430 (7)	0.0600 (9)	0.0393 (7)	0.0039 (6)	0.0021 (6)	−0.0061 (6)
C20	0.0441 (7)	0.0321 (7)	0.0379 (6)	−0.0042 (5)	0.0004 (5)	0.0006 (5)

Geometric parameters (Å, º) top

O1—C11	1.2199 (15)	C8—H8	0.9500
O2—C2	1.3773 (15)	C9—C10	1.4270 (17)
O2—C18	1.4245 (16)	C11—C12	1.4819 (16)
O3—C7	1.3648 (15)	C12—C13	1.3941 (17)
O3—C19	1.4210 (16)	C12—C17	1.4004 (16)
O4—C15	1.3580 (14)	C13—C14	1.3867 (17)
O4—C20	1.4286 (15)	C13—H13	0.9500
C1—C2	1.3807 (17)	C14—C15	1.3936 (16)
C1—C9	1.4216 (17)	C14—H14	0.9500
C1—C11	1.5108 (16)	C15—C16	1.3951 (17)
C2—C3	1.4066 (17)	C16—C17	1.3736 (17)
C3—C4	1.3638 (19)	C16—H16	0.9500
C3—H3	0.9500	C17—H17	0.9500
C4—C10	1.4063 (18)	C18—H18A	0.9800
C4—H4	0.9500	C18—H18B	0.9800
C5—C6	1.3556 (19)	C18—H18C	0.9800
C5—C10	1.4217 (18)	C19—H19A	0.9800
C5—H5	0.9500	C19—H19B	0.9800
C6—C7	1.4172 (18)	C19—H19C	0.9800
C6—H6	0.9500	C20—H20A	0.9800
C7—C8	1.3735 (17)	C20—H20B	0.9800
C8—C9	1.4262 (17)	C20—H20C	0.9800

C2—O2—C18	117.58 (10)	C13—C12—C17	118.17 (11)
C7—O3—C19	118.23 (10)	C13—C12—C11	122.25 (10)
C15—O4—C20	117.68 (9)	C17—C12—C11	119.57 (11)
C2—C1—C9	120.09 (11)	C14—C13—C12	121.71 (10)
C2—C1—C11	118.84 (10)	C14—C13—H13	119.1
C9—C1—C11	121.05 (10)	C12—C13—H13	119.1
O2—C2—C1	115.90 (10)	C13—C14—C15	118.89 (11)
O2—C2—C3	122.82 (11)	C13—C14—H14	120.6
C1—C2—C3	121.28 (12)	C15—C14—H14	120.6
C4—C3—C2	119.21 (12)	O4—C15—C14	124.64 (11)
C4—C3—H3	120.4	O4—C15—C16	115.18 (10)
C2—C3—H3	120.4	C14—C15—C16	120.17 (11)
C3—C4—C10	121.75 (11)	C17—C16—C15	120.12 (11)
C3—C4—H4	119.1	C17—C16—H16	119.9
C10—C4—H4	119.1	C15—C16—H16	119.9
C6—C5—C10	121.54 (12)	C16—C17—C12	120.91 (11)
C6—C5—H5	119.2	C16—C17—H17	119.5
C10—C5—H5	119.2	C12—C17—H17	119.5
C5—C6—C7	119.69 (12)	O2—C18—H18A	109.5
C5—C6—H6	120.2	O2—C18—H18B	109.5
C7—C6—H6	120.2	H18A—C18—H18B	109.5
O3—C7—C8	125.13 (11)	O2—C18—H18C	109.5
O3—C7—C6	113.58 (11)	H18A—C18—H18C	109.5
C8—C7—C6	121.29 (12)	H18B—C18—H18C	109.5
C7—C8—C9	119.71 (11)	O3—C19—H19A	109.5
C7—C8—H8	120.1	O3—C19—H19B	109.5
C9—C8—H8	120.1	H19A—C19—H19B	109.5
C1—C9—C8	122.65 (11)	O3—C19—H19C	109.5
C1—C9—C10	118.25 (11)	H19A—C19—H19C	109.5
C8—C9—C10	119.10 (11)	H19B—C19—H19C	109.5
C4—C10—C5	122.03 (11)	O4—C20—H20A	109.5
C4—C10—C9	119.33 (12)	O4—C20—H20B	109.5
C5—C10—C9	118.64 (11)	H20A—C20—H20B	109.5
O1—C11—C12	122.00 (11)	O4—C20—H20C	109.5
O1—C11—C1	121.09 (11)	H20A—C20—H20C	109.5
C12—C11—C1	116.90 (10)	H20B—C20—H20C	109.5

C18—O2—C2—C1	−165.55 (12)	C6—C5—C10—C9	1.9 (2)
C18—O2—C2—C3	14.60 (18)	C1—C9—C10—C4	−1.07 (17)
C9—C1—C2—O2	177.39 (10)	C8—C9—C10—C4	178.91 (11)
C11—C1—C2—O2	−4.15 (17)	C1—C9—C10—C5	179.46 (11)
C9—C1—C2—C3	−2.75 (19)	C8—C9—C10—C5	−0.56 (18)
C11—C1—C2—C3	175.71 (11)	C2—C1—C11—O1	105.40 (14)
O2—C2—C3—C4	179.84 (12)	C9—C1—C11—O1	−76.15 (15)
C1—C2—C3—C4	0.0 (2)	C2—C1—C11—C12	−75.42 (14)
C2—C3—C4—C10	2.2 (2)	C9—C1—C11—C12	103.03 (13)
C10—C5—C6—C7	−1.5 (2)	O1—C11—C12—C13	165.98 (11)
C19—O3—C7—C8	−8.7 (2)	C1—C11—C12—C13	−13.19 (16)
C19—O3—C7—C6	171.37 (12)	O1—C11—C12—C17	−12.62 (17)
C5—C6—C7—O3	179.62 (12)	C1—C11—C12—C17	168.21 (10)
C5—C6—C7—C8	−0.3 (2)	C17—C12—C13—C14	1.17 (16)
O3—C7—C8—C9	−178.27 (12)	C11—C12—C13—C14	−177.45 (10)
C6—C7—C8—C9	1.65 (19)	C12—C13—C14—C15	−1.44 (17)
C2—C1—C9—C8	−176.75 (11)	C20—O4—C15—C14	4.39 (16)
C11—C1—C9—C8	4.82 (18)	C20—O4—C15—C16	−174.64 (10)
C2—C1—C9—C10	3.23 (17)	C13—C14—C15—O4	−178.69 (10)
C11—C1—C9—C10	−175.20 (11)	C13—C14—C15—C16	0.29 (17)
C7—C8—C9—C1	178.80 (11)	O4—C15—C16—C17	−179.82 (10)
C7—C8—C9—C10	−1.18 (18)	C14—C15—C16—C17	1.10 (17)
C3—C4—C10—C5	177.77 (13)	C15—C16—C17—C12	−1.38 (18)
C3—C4—C10—C9	−1.68 (19)	C13—C12—C17—C16	0.26 (17)
C6—C5—C10—C4	−177.53 (13)	C11—C12—C17—C16	178.92 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3ⁱ	0.95	2.51	3.4592 (16)	178

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈O₄
M_r	322.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	14.9638 (2), 7.9191 (1), 13.6394 (2)
β (°)	92.56
V (Å³)	1614.64 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.60 × 0.40 × 0.30

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.662, 0.806
No. of measured, independent and observed [I > 2σ(I)] reflections	27665, 2957, 2701
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.106, 1.05
No. of reflections	2957
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.18

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku, 2010), Il Milione (Burla et al., 2007), 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
C6—H6···O3ⁱ	0.95	2.51	3.4592 (16)	178

Symmetry code: (i) −x, −y, −z.

Acknowledgements

The authors express their gratitude to Master Toyokazu Muto, Department of Organic and Polymer Materials Chemistry, Graduate School, Tokyo University of Agriculture & Technology, and Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, for their technical advice. This work was partially supported by the Iron and Steel Institute of Japan (ISIJ) Research Promotion Grant, Tokyo, Japan.

References

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