(8-Benzoyl-2,7-dimeth­oxy­naphthalen-1-yl)(4-phen­oxy­phen­yl)methanone

Sasagawa, K.; Sakamoto, R.; Takeuchi, R.; Yonezawa, N.; Okamoto, A.

doi:10.1107/S1600536813004303

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Pages o395-o396

doi:10.1107/S1600536813004303

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(8-Benzoyl-2,7-dimethoxynaphthalen-1-yl)(4-phenoxyphenyl)methanone

Kosuke Sasagawa,^a Rei Sakamoto,^a Ryo Takeuchi,^a Noriyuki Yonezawa ^a and Akiko Okamoto ^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 9 February 2013; accepted 13 February 2013; online 20 February 2013)

In the molecule of the title compound, C₃₂H₂₄O₅, the benzoyl group and the 4-phenoxy substituted benzoyl group at the 1- and 8-positions of the naphthalene ring system are aligned almost antiparallel. The two benzene rings make a dihedral angle of 21.18 (10)°, and are inclined to the naphthalene ring system by 86.53 (9) and 82.95 (8)°, respectively. In the crystal, C—H⋯O interactions are observed involving aromatic and methoxy H atoms with ketonic carbonyl O atoms, as well as C—H⋯π interactions between aromatic H atoms and the π-systems of naphthalene and benzene rings. These interactions form a three-dimensional architecture and afford a waved alignment of the naphthalene ring systems along the c axis.

Related literature

For the synthesis 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 ); Sasagawa et al. (2011 , 2013 ); Muto et al. (2012 ).

Experimental

Crystal data

C₃₂H₂₄O₅
M_r = 488.51
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.19645 (10) Å
b = 11.5051 (2) Å
c = 26.4916 (4) Å
V = 2498.18 (7) Å³
Z = 4
Cu Kα radiation
μ = 0.71 mm⁻¹
T = 193 K
0.60 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ) T_min = 0.802, T_max = 0.868
46867 measured reflections
2605 independent reflections
2543 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.085
S = 1.04
2605 reflections
337 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C27–C32, C12–C17 and C5–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C30—H30⋯O5ⁱ	0.95	2.52	3.423 (3)	158
C7—H7⋯O5ⁱⁱ	0.95	2.37	3.304 (3)	168
C25—H25B⋯O5ⁱⁱ	0.98	2.34	3.122 (3)	136
C3—H3⋯O1ⁱⁱⁱ	0.95	2.40	3.310 (2)	160
C20—H20⋯Cg1^iv	0.95	2.84	3.652 (3)	144
C23—H23⋯Cg2^v	0.95	2.76	3.628 (2)	151
C29—H29⋯Cg3ⁱ	0.95	2.85	3.652 (3)	142
Symmetry codes: (i) x+1, y, z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iv) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+1]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; 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/S1600536813004303/vm2188sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004303/vm2188Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813004303/vm2188Isup3.cml

checkCIF report

Comment top

In the course of our study on selective electrophilic aromatic aroylation of the naphthalene ring core, 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), {8-[4-(butoxy)benzoyl]-2,7-dimethoxynaphthalen-1-yl}[4-(butoxy)phenyl] methanone [1,8-bis(4-butoxylbenzoyl)-2,7-dimethoxynaphthalene] (Sasagawa et al., 2011) and [2,7-dimethoxy-8-(4-methoxybenzoyl)-naphthalen-1-yl](4-methoxyphenyl) methanone chloroform monosolvate [1,8-bis(4-methoxybenzoyl)-2,7-dimethoxynaphthalene] (Sasagawa et al., 2013).

The aroyl groups in the 1,8-diaroylnaphthalene compounds are almost perpendicular to the naphthalene rings, and oriented in opposite directions (anti-orientation). According to our knowledge, most 1,8-diaroylnaphthalene derivatives have anti-oriented structures. Recently, we have also clarified another structure of the 1,8-diaroylnaphthalene derivatives, in which the two aroyl groups are situated in same direction (syn-orientation), [2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene; Hijikata et al., 2010].

Moreover, we have reported the asymmetric 1,8-diaroylnaphthalene derivatives, [8-(4-chlorobenzoyl)-2,7-dimethoxynaphthalen-1-yl](2,4,6-trimethylphenyl) methanone (Muto et al., 2012). As a part of our ongoing studies on the molecular structures of these kinds of asymmetric homologous molecules, the X-ray crystal structure of the title compound, 2,7-dimethoxynaphthalene bearing benzoyl and phenoxybenzoyl groups at the 1,8-positions, is discussed in this article.

The molecular structure of the title compound is displayed in Fig 1. The benzoyl group and 4-phenoxybenzoyl group are situated in the anti-orientation. The dihedral angle between the best planes of the benzene rings of two kinds of benzoyl groups is 21.18 (10) °. The dihedral angles of the best planes of the benzene rings of the benzoyl moiety and 4-phenoxybenzoyl moiety with the naphthalene ring are 86.53 (9) and 82.95 (8) °, respectively. In addition, the dihedral angle between both benzene rings of the 4-phenoxyphenyl moiety is 69.19 (10) °.

The two ketonic carbonyl moieties (C11=O1, C26=O5) and the benzene ring of two benzoyl moieties lie in the same plane [torsion angle O1—C11—C12—C13 = 7.3 (2) °, O5—C26—C27—C32 = 1.3 (3) °]. In the crystal, C—H···O and C—H···π interactions effectively contribute to the stabilization of the molecular packing (Table 1): a C—H···O interaction between the hydrogen atom of the 4-position of the benzoyl group and the oxygen atom of the carbonyl moiety in the benzoyl group, a C—H···π interaction between the hydrogen atom of the 3-position of the benzoyl group and the π-system of the naphthalene ring (Fig. 2), C—H···O interactions of a hydrogen atom of the methoxy group at the 2-position of the naphthalene ring and a hydrogen atom at the 3-position of the naphthalene ring with the carbonyl oxygen atom of the benzoyl group, a C—H···π interaction between the hydrogen atom of the 3-position of the phenoxy moiety and the π-system of the benzoyl group (Fig. 3), a C—H···O interaction between the hydrogen atom at the 6-position of the naphthalene ring and the carbonyl oxygen atom of the phenoxybenzoyl group (Fig. 4), and a C—H···π interaction between the hydrogen atom of the 6-position of the phenoxy moiety and the π-system of the internal benzene ring of 4-phenoxybenzoyl group.

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); Sasagawa et al. (2011, 2013); Muto et al. (2012).

Experimental top

In a 10 ml one-necked flask, [8-(4-benzoyl)-2,7-dimethoxynaphthalen-1-yl](4-fluorophenyl)-methanone (1.0 mmol, 414 mg), phenol (1.5 mmol, 141 mg), potassium carbonate (2.5 mmol, 346 mg) and freshly distilled dimethylacetamide (2.5 ml) were stirred at 423 K for 6 h. This mixture was poured into 2M aqueous HCl (100 ml). The aqueous layer was extracted with ethyl acetate (20 ml × 3). The combined extracts were washed with water 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 (yield 88%). The crude product was purified by recrystallization from methanol (yield 47%). Colorless platelet single crystals suitable for X-ray diffraction were obtained by repeated crystallization from ethanol.

Spectroscopic Data:

¹H NMR δ (500 MHz, CDCl₃): 3.69 (3H, s), 3.72 (3H, s), 6.86 (2H, d, J = 8.5 Hz), 7.09 (2H, d, J = 7.5 Hz), 7.16–7.22 (3H, m), 7.32–7.71 (4H, m), 7.50 (1H, t, J = 7.5 Hz), 7.64–7.71 (4H, m), 7.94 (1H, d, J = 9.0 Hz), 7.95 (1H, d, J = 9.0 Hz) p.p.m.

¹³C NMR δ (125 MHz, CDCl₃): 56.39, 56.45, 111.18, 116.70, 120.28, 121.43, 121.46, 124.33, 124.34, 125.49, 127.94, 129.07, 129.66, 129.86, 131.38, 131.93, 131.99, 132.57, 133.49, 138.59, 155.52, 156.07, 156.23, 161.51, 195.29, 196.72 p.p.m.

IR (KBr): 1659 (C=O), 1599, 1580, 1512 (Ar), 1240 (OMe) cm^-1

HRMS (m/z): [M+H]⁺ calcd. for C₃₂H₂₅O_5, 489.1702, found, 489.1690

m.p. = 466.1—469.7 K

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); 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. Hydrogen atoms are shown as small spheres of arbitrary radius.
	Fig. 2. Intermolecular C—H···O interactions between H30 and O5 [symmetry code: 1 + x, y, z] along the a axis (dashed lines).
	Fig. 3. Intermolecular C—H···O interactions between H25B and O5, H7 and O5 [symmetry code: -x, 1/2 + y, 1/2 - z] along the b axis (dashed lines).
	Fig. 4. Intermolecular C—H···O interactions between H3 and O1 [symmetry code: -1/2 + x, 1/2 - y, 1 - z] along the c axis (dashed lines).

(8-Benzoyl-2,7-dimethoxynaphthalen-1-yl)(4-phenoxyphenyl)methanone top

Crystal data top

C₃₂H₂₄O₅	F(000) = 1024
M_r = 488.51	D_x = 1.299 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2ac 2ab	Cell parameters from 44479 reflections
a = 8.19645 (10) Å	θ = 3.3–68.3°
b = 11.5051 (2) Å	µ = 0.71 mm⁻¹
c = 26.4916 (4) Å	T = 193 K
V = 2498.18 (7) Å³	Block, colourless
Z = 4	0.60 × 0.30 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2605 independent reflections
Radiation source: rotating anode	2543 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 10.000 pixels mm^-1	θ_max = 68.3°, θ_min = 3.3°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	k = −13→13
T_min = 0.802, T_max = 0.868	l = −31→31
46867 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)] = 0.032	H-atom parameters constrained
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0545P)² + 0.3758P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2605 reflections	Δρ_max = 0.19 e Å⁻³
337 parameters	Δρ_min = −0.14 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: 0.0019 (2)

Crystal data top

C₃₂H₂₄O₅	V = 2498.18 (7) Å³
M_r = 488.51	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 8.19645 (10) Å	µ = 0.71 mm⁻¹
b = 11.5051 (2) Å	T = 193 K
c = 26.4916 (4) Å	0.60 × 0.30 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2605 independent reflections
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	2543 reflections with I > 2σ(I)
T_min = 0.802, T_max = 0.868	R_int = 0.030
46867 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.04	Δρ_max = 0.19 e Å⁻³
2605 reflections	Δρ_min = −0.14 e Å⁻³
337 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	0.31166 (15)	0.05570 (11)	0.41889 (5)	0.0395 (3)
O2	−0.2584 (2)	−0.31098 (13)	0.44425 (6)	0.0630 (5)
O3	0.08516 (19)	0.16347 (12)	0.50987 (4)	0.0461 (3)
O4	0.1135 (2)	0.25452 (15)	0.24234 (5)	0.0582 (4)
O5	0.11094 (17)	0.02780 (12)	0.31322 (5)	0.0429 (3)
C1	0.0961 (2)	0.19406 (14)	0.42338 (6)	0.0334 (4)
C2	0.0552 (2)	0.23680 (15)	0.47042 (7)	0.0374 (4)
C3	−0.0139 (3)	0.34833 (17)	0.47642 (7)	0.0429 (4)
H3	−0.0370	0.3778	0.5091	0.051*
C4	−0.0469 (2)	0.41295 (15)	0.43472 (7)	0.0432 (4)
H4	−0.0976	0.4867	0.4387	0.052*
C5	−0.0081 (2)	0.37364 (15)	0.38559 (7)	0.0381 (4)
C6	−0.0466 (3)	0.44090 (16)	0.34258 (8)	0.0450 (4)
H6	−0.0998	0.5136	0.3469	0.054*
C7	−0.0093 (3)	0.40417 (18)	0.29486 (8)	0.0475 (5)
H7	−0.0373	0.4501	0.2663	0.057*
C8	0.0710 (2)	0.29759 (18)	0.28879 (7)	0.0416 (4)
C9	0.1126 (2)	0.22877 (15)	0.32944 (6)	0.0347 (4)
C10	0.0701 (2)	0.26357 (14)	0.37942 (6)	0.0328 (4)
C11	0.1648 (2)	0.07161 (15)	0.42218 (6)	0.0330 (4)
C12	0.0487 (2)	−0.02714 (15)	0.42656 (6)	0.0353 (4)
C13	0.1101 (3)	−0.13927 (16)	0.43272 (7)	0.0421 (4)
H13	0.2247	−0.1516	0.4335	0.050*
C14	0.0055 (3)	−0.23210 (16)	0.43770 (8)	0.0476 (5)
H14	0.0477	−0.3083	0.4422	0.057*
C15	−0.1609 (3)	−0.21421 (18)	0.43615 (7)	0.0466 (5)
C16	−0.2252 (3)	−0.10405 (19)	0.42947 (8)	0.0512 (5)
H16	−0.3399	−0.0925	0.4280	0.061*
C17	−0.1191 (3)	−0.01104 (17)	0.42499 (8)	0.0436 (4)
H17	−0.1618	0.0651	0.4208	0.052*
C18	−0.3900 (3)	−0.33373 (16)	0.41261 (7)	0.0440 (4)
C19	−0.3950 (3)	−0.3008 (2)	0.36259 (8)	0.0556 (5)
H19	−0.3112	−0.2534	0.3488	0.067*
C20	−0.5230 (3)	−0.3373 (2)	0.33277 (9)	0.0665 (7)
H20	−0.5275	−0.3144	0.2983	0.080*
C21	−0.6440 (3)	−0.4065 (2)	0.35234 (11)	0.0697 (7)
H21	−0.7308	−0.4327	0.3315	0.084*
C22	−0.6383 (3)	−0.4377 (2)	0.40272 (10)	0.0657 (7)
H22	−0.7229	−0.4843	0.4166	0.079*
C23	−0.5117 (3)	−0.40221 (19)	0.43289 (8)	0.0536 (5)
H23	−0.5079	−0.4245	0.4674	0.064*
C24	0.0591 (3)	0.2062 (2)	0.55989 (7)	0.0537 (5)
H24A	−0.0567	0.2248	0.5644	0.064*
H24B	0.1247	0.2763	0.5652	0.064*
H24C	0.0914	0.1466	0.5844	0.064*
C25	0.0032 (3)	0.2714 (2)	0.20238 (8)	0.0599 (6)
H25A	0.0191	0.2106	0.1770	0.072*
H25B	0.0223	0.3477	0.1870	0.072*
H25C	−0.1087	0.2677	0.2153	0.072*
C26	0.1933 (2)	0.11466 (16)	0.31671 (6)	0.0340 (4)
C27	0.3730 (2)	0.11156 (18)	0.30852 (6)	0.0375 (4)
C28	0.4689 (2)	0.2093 (2)	0.31499 (7)	0.0458 (5)
H28	0.4203	0.2820	0.3230	0.055*
C29	0.6378 (3)	0.2002 (3)	0.30959 (9)	0.0597 (6)
H29	0.7048	0.2666	0.3146	0.072*
C30	0.7076 (3)	0.0954 (3)	0.29705 (9)	0.0633 (6)
H30	0.8226	0.0898	0.2935	0.076*
C31	0.6119 (3)	−0.0014 (2)	0.28961 (10)	0.0641 (6)
H31	0.6606	−0.0733	0.2804	0.077*
C32	0.4452 (3)	0.0062 (2)	0.29560 (9)	0.0519 (5)
H32	0.3793	−0.0609	0.2909	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0357 (7)	0.0423 (7)	0.0407 (6)	0.0005 (6)	−0.0008 (5)	−0.0043 (5)
O2	0.0731 (11)	0.0508 (8)	0.0652 (9)	−0.0268 (8)	−0.0251 (9)	0.0206 (7)
O3	0.0606 (9)	0.0469 (7)	0.0309 (6)	0.0056 (7)	0.0013 (6)	−0.0039 (5)
O4	0.0563 (9)	0.0850 (11)	0.0335 (6)	0.0205 (9)	0.0023 (6)	0.0061 (7)
O5	0.0376 (7)	0.0425 (7)	0.0486 (7)	−0.0058 (6)	0.0001 (6)	−0.0108 (6)
C1	0.0326 (9)	0.0323 (8)	0.0353 (8)	−0.0049 (7)	0.0005 (7)	−0.0028 (7)
C2	0.0385 (9)	0.0365 (9)	0.0373 (8)	−0.0046 (8)	0.0015 (8)	−0.0042 (7)
C3	0.0465 (11)	0.0398 (9)	0.0423 (10)	−0.0036 (9)	0.0075 (9)	−0.0118 (8)
C4	0.0442 (10)	0.0293 (8)	0.0562 (11)	−0.0002 (8)	0.0080 (9)	−0.0082 (8)
C5	0.0358 (9)	0.0293 (8)	0.0492 (10)	−0.0041 (8)	0.0034 (8)	−0.0003 (7)
C6	0.0432 (10)	0.0326 (9)	0.0594 (11)	0.0010 (8)	0.0046 (9)	0.0058 (8)
C7	0.0460 (11)	0.0468 (10)	0.0497 (10)	0.0018 (10)	0.0007 (9)	0.0144 (9)
C8	0.0363 (10)	0.0498 (10)	0.0386 (9)	−0.0014 (9)	0.0035 (8)	0.0065 (8)
C9	0.0296 (8)	0.0373 (9)	0.0372 (9)	−0.0028 (8)	0.0005 (7)	0.0010 (7)
C10	0.0305 (8)	0.0301 (8)	0.0377 (8)	−0.0050 (7)	0.0012 (7)	−0.0025 (7)
C11	0.0395 (9)	0.0338 (8)	0.0257 (7)	−0.0016 (7)	−0.0016 (7)	−0.0032 (6)
C12	0.0418 (10)	0.0333 (8)	0.0308 (8)	−0.0028 (8)	−0.0026 (7)	−0.0009 (7)
C13	0.0450 (10)	0.0371 (9)	0.0441 (10)	0.0008 (9)	−0.0056 (9)	−0.0009 (8)
C14	0.0607 (13)	0.0321 (9)	0.0501 (10)	−0.0026 (9)	−0.0120 (10)	0.0028 (8)
C15	0.0568 (12)	0.0402 (10)	0.0429 (9)	−0.0141 (9)	−0.0099 (9)	0.0061 (8)
C16	0.0432 (11)	0.0484 (11)	0.0619 (12)	−0.0089 (10)	−0.0056 (10)	0.0059 (10)
C17	0.0440 (10)	0.0346 (9)	0.0523 (11)	−0.0014 (8)	−0.0006 (9)	0.0021 (8)
C18	0.0490 (11)	0.0372 (9)	0.0457 (10)	−0.0064 (9)	−0.0048 (9)	0.0007 (8)
C19	0.0554 (13)	0.0614 (13)	0.0500 (11)	−0.0127 (12)	−0.0002 (10)	0.0091 (10)
C20	0.0739 (17)	0.0763 (15)	0.0492 (12)	−0.0144 (15)	−0.0147 (12)	0.0059 (11)
C21	0.0610 (15)	0.0718 (15)	0.0764 (15)	−0.0165 (14)	−0.0230 (13)	0.0024 (13)
C22	0.0521 (13)	0.0650 (15)	0.0799 (16)	−0.0196 (13)	−0.0008 (12)	0.0079 (12)
C23	0.0609 (13)	0.0502 (11)	0.0498 (11)	−0.0139 (11)	0.0020 (10)	0.0055 (9)
C24	0.0649 (14)	0.0632 (12)	0.0329 (9)	0.0060 (12)	0.0038 (9)	−0.0084 (9)
C25	0.0696 (15)	0.0599 (13)	0.0503 (11)	0.0168 (13)	−0.0132 (11)	−0.0093 (10)
C26	0.0340 (9)	0.0408 (9)	0.0273 (7)	−0.0001 (8)	−0.0015 (7)	−0.0035 (7)
C27	0.0330 (9)	0.0494 (10)	0.0301 (8)	0.0016 (8)	−0.0010 (7)	0.0007 (8)
C28	0.0383 (10)	0.0595 (12)	0.0395 (9)	−0.0057 (10)	0.0019 (8)	−0.0073 (9)
C29	0.0379 (11)	0.0877 (17)	0.0536 (12)	−0.0151 (12)	0.0018 (9)	−0.0076 (12)
C30	0.0320 (10)	0.0962 (19)	0.0618 (13)	0.0077 (13)	0.0013 (10)	0.0102 (14)
C31	0.0475 (12)	0.0696 (15)	0.0753 (15)	0.0188 (12)	0.0093 (12)	0.0099 (13)
C32	0.0427 (11)	0.0504 (12)	0.0625 (13)	0.0074 (10)	0.0058 (10)	0.0041 (10)

Geometric parameters (Å, º) top

O1—C11	1.220 (2)	C16—C17	1.384 (3)
O2—C15	1.387 (2)	C16—H16	0.9500
O2—C18	1.391 (2)	C17—H17	0.9500
O3—C2	1.365 (2)	C18—C19	1.379 (3)
O3—C24	1.429 (2)	C18—C23	1.380 (3)
O4—C8	1.372 (2)	C19—C20	1.378 (3)
O4—C25	1.406 (3)	C19—H19	0.9500
O5—C26	1.209 (2)	C20—C21	1.374 (4)
C1—C2	1.381 (2)	C20—H20	0.9500
C1—C10	1.429 (2)	C21—C22	1.383 (4)
C1—C11	1.518 (2)	C21—H21	0.9500
C2—C3	1.412 (3)	C22—C23	1.372 (3)
C3—C4	1.359 (3)	C22—H22	0.9500
C3—H3	0.9500	C23—H23	0.9500
C4—C5	1.414 (3)	C24—H24A	0.9800
C4—H4	0.9500	C24—H24B	0.9800
C5—C6	1.413 (3)	C24—H24C	0.9800
C5—C10	1.428 (2)	C25—H25A	0.9800
C6—C7	1.368 (3)	C25—H25B	0.9800
C6—H6	0.9500	C25—H25C	0.9800
C7—C8	1.401 (3)	C26—C27	1.489 (2)
C7—H7	0.9500	C27—C28	1.383 (3)
C8—C9	1.379 (3)	C27—C32	1.392 (3)
C9—C10	1.427 (2)	C28—C29	1.396 (3)
C9—C26	1.508 (3)	C28—H28	0.9500
C11—C12	1.487 (2)	C29—C30	1.375 (4)
C12—C17	1.388 (3)	C29—H29	0.9500
C12—C13	1.394 (3)	C30—C31	1.377 (4)
C13—C14	1.376 (3)	C30—H30	0.9500
C13—H13	0.9500	C31—C32	1.378 (3)
C14—C15	1.380 (3)	C31—H31	0.9500
C14—H14	0.9500	C32—H32	0.9500
C15—C16	1.384 (3)

C15—O2—C18	120.31 (15)	C12—C17—H17	119.4
C2—O3—C24	118.06 (16)	C19—C18—C23	120.6 (2)
C8—O4—C25	117.51 (17)	C19—C18—O2	123.43 (19)
C2—C1—C10	120.00 (15)	C23—C18—O2	115.69 (18)
C2—C1—C11	116.07 (15)	C20—C19—C18	119.3 (2)
C10—C1—C11	123.92 (15)	C20—C19—H19	120.3
O3—C2—C1	115.28 (15)	C18—C19—H19	120.3
O3—C2—C3	123.22 (16)	C21—C20—C19	120.7 (2)
C1—C2—C3	121.50 (16)	C21—C20—H20	119.7
C4—C3—C2	119.07 (17)	C19—C20—H20	119.7
C4—C3—H3	120.5	C20—C21—C22	119.4 (2)
C2—C3—H3	120.5	C20—C21—H21	120.3
C3—C4—C5	121.89 (17)	C22—C21—H21	120.3
C3—C4—H4	119.1	C23—C22—C21	120.7 (2)
C5—C4—H4	119.1	C23—C22—H22	119.6
C6—C5—C4	121.11 (17)	C21—C22—H22	119.6
C6—C5—C10	119.57 (16)	C22—C23—C18	119.3 (2)
C4—C5—C10	119.32 (16)	C22—C23—H23	120.3
C7—C6—C5	121.75 (17)	C18—C23—H23	120.3
C7—C6—H6	119.1	O3—C24—H24A	109.5
C5—C6—H6	119.1	O3—C24—H24B	109.5
C6—C7—C8	118.78 (17)	H24A—C24—H24B	109.5
C6—C7—H7	120.6	O3—C24—H24C	109.5
C8—C7—H7	120.6	H24A—C24—H24C	109.5
O4—C8—C9	115.46 (17)	H24B—C24—H24C	109.5
O4—C8—C7	122.59 (17)	O4—C25—H25A	109.5
C9—C8—C7	121.95 (17)	O4—C25—H25B	109.5
C8—C9—C10	120.18 (17)	H25A—C25—H25B	109.5
C8—C9—C26	115.71 (16)	O4—C25—H25C	109.5
C10—C9—C26	123.98 (15)	H25A—C25—H25C	109.5
C9—C10—C5	117.68 (15)	H25B—C25—H25C	109.5
C9—C10—C1	124.26 (15)	O5—C26—C27	121.40 (18)
C5—C10—C1	118.03 (15)	O5—C26—C9	119.47 (15)
O1—C11—C12	121.49 (16)	C27—C26—C9	119.13 (17)
O1—C11—C1	120.45 (16)	C28—C27—C32	119.81 (18)
C12—C11—C1	118.04 (15)	C28—C27—C26	121.65 (19)
C17—C12—C13	118.98 (18)	C32—C27—C26	118.52 (19)
C17—C12—C11	122.00 (17)	C27—C28—C29	119.3 (2)
C13—C12—C11	119.02 (17)	C27—C28—H28	120.3
C14—C13—C12	120.31 (19)	C29—C28—H28	120.3
C14—C13—H13	119.8	C30—C29—C28	120.2 (2)
C12—C13—H13	119.8	C30—C29—H29	119.9
C13—C14—C15	119.80 (19)	C28—C29—H29	119.9
C13—C14—H14	120.1	C29—C30—C31	120.5 (2)
C15—C14—H14	120.1	C29—C30—H30	119.8
C14—C15—C16	121.14 (19)	C31—C30—H30	119.8
C14—C15—O2	116.44 (19)	C30—C31—C32	119.8 (2)
C16—C15—O2	122.33 (19)	C30—C31—H31	120.1
C17—C16—C15	118.6 (2)	C32—C31—H31	120.1
C17—C16—H16	120.7	C31—C32—C27	120.3 (2)
C15—C16—H16	120.7	C31—C32—H32	119.8
C16—C17—C12	121.12 (19)	C27—C32—H32	119.8
C16—C17—H17	119.4

C24—O3—C2—C1	174.60 (18)	O1—C11—C12—C13	7.3 (3)
C24—O3—C2—C3	−5.9 (3)	C1—C11—C12—C13	−171.04 (16)
C10—C1—C2—O3	−179.94 (15)	C17—C12—C13—C14	−0.7 (3)
C11—C1—C2—O3	1.2 (2)	C11—C12—C13—C14	178.93 (16)
C10—C1—C2—C3	0.6 (3)	C12—C13—C14—C15	0.6 (3)
C11—C1—C2—C3	−178.30 (16)	C13—C14—C15—C16	0.2 (3)
O3—C2—C3—C4	−176.71 (18)	C13—C14—C15—O2	−176.52 (16)
C1—C2—C3—C4	2.7 (3)	C18—O2—C15—C14	−133.4 (2)
C2—C3—C4—C5	−2.6 (3)	C18—O2—C15—C16	49.9 (3)
C3—C4—C5—C6	178.59 (19)	C14—C15—C16—C17	−0.8 (3)
C3—C4—C5—C10	−0.8 (3)	O2—C15—C16—C17	175.70 (19)
C4—C5—C6—C7	179.8 (2)	C15—C16—C17—C12	0.7 (3)
C10—C5—C6—C7	−0.8 (3)	C13—C12—C17—C16	0.1 (3)
C5—C6—C7—C8	−0.8 (3)	C11—C12—C17—C16	−179.56 (17)
C25—O4—C8—C9	141.6 (2)	C15—O2—C18—C19	29.0 (3)
C25—O4—C8—C7	−38.4 (3)	C15—O2—C18—C23	−157.0 (2)
C6—C7—C8—O4	−179.69 (19)	C23—C18—C19—C20	−0.3 (4)
C6—C7—C8—C9	0.3 (3)	O2—C18—C19—C20	173.4 (2)
O4—C8—C9—C10	−178.22 (17)	C18—C19—C20—C21	−0.5 (4)
C7—C8—C9—C10	1.8 (3)	C19—C20—C21—C22	1.2 (4)
O4—C8—C9—C26	−2.1 (2)	C20—C21—C22—C23	−1.3 (4)
C7—C8—C9—C26	177.96 (17)	C21—C22—C23—C18	0.6 (4)
C8—C9—C10—C5	−3.3 (3)	C19—C18—C23—C22	0.2 (4)
C26—C9—C10—C5	−179.09 (16)	O2—C18—C23—C22	−174.0 (2)
C8—C9—C10—C1	174.74 (17)	C8—C9—C26—O5	−94.6 (2)
C26—C9—C10—C1	−1.0 (3)	C10—C9—C26—O5	81.4 (2)
C6—C5—C10—C9	2.8 (3)	C8—C9—C26—C27	85.2 (2)
C4—C5—C10—C9	−177.78 (17)	C10—C9—C26—C27	−98.9 (2)
C6—C5—C10—C1	−175.38 (17)	O5—C26—C27—C28	−176.63 (17)
C4—C5—C10—C1	4.1 (2)	C9—C26—C27—C28	3.6 (3)
C2—C1—C10—C9	178.04 (17)	O5—C26—C27—C32	1.3 (3)
C11—C1—C10—C9	−3.2 (3)	C9—C26—C27—C32	−178.47 (17)
C2—C1—C10—C5	−3.9 (2)	C32—C27—C28—C29	−1.5 (3)
C11—C1—C10—C5	174.87 (15)	C26—C27—C28—C29	176.44 (18)
C2—C1—C11—O1	−100.0 (2)	C27—C28—C29—C30	1.2 (3)
C10—C1—C11—O1	81.2 (2)	C28—C29—C30—C31	0.1 (4)
C2—C1—C11—C12	78.3 (2)	C29—C30—C31—C32	−1.1 (4)
C10—C1—C11—C12	−100.50 (19)	C30—C31—C32—C27	0.8 (4)
O1—C11—C12—C17	−173.09 (18)	C28—C27—C32—C31	0.5 (3)
C1—C11—C12—C17	8.6 (2)	C26—C27—C32—C31	−177.5 (2)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C27–C32, C12–C17 and C5–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30···O5ⁱ	0.95	2.52	3.423 (3)	158
C7—H7···O5ⁱⁱ	0.95	2.37	3.304 (3)	168
C25—H25B···O5ⁱⁱ	0.98	2.34	3.122 (3)	136
C3—H3···O1ⁱⁱⁱ	0.95	2.40	3.310 (2)	160
C20—H20···Cg1^iv	0.95	2.84	3.652 (3)	144
C23—H23···Cg2^v	0.95	2.76	3.628 (2)	151
C29—H29···Cg3ⁱ	0.95	2.85	3.652 (3)	142

Symmetry codes: (i) x+1, y, z; (ii) −x, y+1/2, −z+1/2; (iii) x−1/2, −y+1/2, −z+1; (iv) −x, y−1/2, −z+1/2; (v) x−1/2, −y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₃₂H₂₄O₅
M_r	488.51
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	193
a, b, c (Å)	8.19645 (10), 11.5051 (2), 26.4916 (4)
V (Å³)	2498.18 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.60 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Rigaku, 1995)
T_min, T_max	0.802, 0.868
No. of measured, independent and observed [I > 2σ(I)] reflections	46867, 2605, 2543
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.085, 1.04
No. of reflections	2605
No. of parameters	337
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.14

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

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C27–C32, C12–C17 and C5–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30···O5ⁱ	0.95	2.52	3.423 (3)	158
C7—H7···O5ⁱⁱ	0.95	2.37	3.304 (3)	168
C25—H25B···O5ⁱⁱ	0.98	2.34	3.122 (3)	136
C3—H3···O1ⁱⁱⁱ	0.95	2.40	3.310 (2)	160
C20—H20···Cg1^iv	0.95	2.84	3.652 (3)	144
C23—H23···Cg2^v	0.95	2.76	3.628 (2)	151
C29—H29···Cg3ⁱ	0.95	2.85	3.652 (3)	142

Symmetry codes: (i) x+1, y, z; (ii) −x, y+1/2, −z+1/2; (iii) x−1/2, −y+1/2, −z+1; (iv) −x, y−1/2, −z+1/2; (v) x−1/2, −y−1/2, −z+1.

Acknowledgements

Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, is thanked for his technical advice. This work was partially supported by the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.

References

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Volume 69| Part 3| March 2013| Pages o395-o396

doi:10.1107/S1600536813004303

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