(8-Benzoyl-2,7-dieth­oxy­naphthalen-1-yl)(phen­yl)methanone

Isogai, A.; Tsumuki, T.; Murohashi, S.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536812049963

organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page o71

https://doi.org/10.1107/S1600536812049963

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(8-Benzoyl-2,7-diethoxynaphthalen-1-yl)(phenyl)methanone

Atsumi Isogai,^a Takehiro Tsumuki,^a Shun Murohashi,^a Akiko Okamoto ^a ^* and Noriyuki Yonezawa ^a

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

(Received 5 December 2012; accepted 6 December 2012; online 12 December 2012)

In the title compound, C₂₈H₂₄O₄, the benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost antiparallel, and the benzene rings make a dihedral angle of 20.03 (7)°. The dihedral angles between the benzene rings and the naphthalene ring system are 68.42 (5) and 71.69 (5)°. In the crystal, adjacent molecules are linked via C—H⋯O hydrogen bonds, forming chains propagating along [100].

Related literature

For electrophilic aroylation of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ); Okamoto et al. (2011 ). For the structures of closely related compounds, see: Nakaema et al. (2008 ); Nishijima et al. (2010 ); Sasagawa et al. (2011 ); Tsumuki et al. (2011 ); Muto et al. (2012 ).

Experimental

Crystal data

C₂₈H₂₄O₄
M_r = 424.47
Monoclinic, P 2₁ /n
a = 7.92185 (14) Å
b = 20.6794 (4) Å
c = 14.2130 (3) Å
β = 106.043 (1)°
V = 2237.68 (7) Å³
Z = 4
Cu Kα radiation
μ = 0.67 mm⁻¹
T = 193 K
0.60 × 0.50 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.689, T_max = 0.936
39782 measured reflections
4076 independent reflections
3736 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.091
S = 1.05
4076 reflections
292 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O3ⁱ	0.95	2.37	3.2404 (16)	153
C21—H21⋯O4ⁱⁱ	0.95	2.39	3.3326 (16)	171
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

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: https://doi.org/10.1107/S1600536812049963/su2538sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049963/su2538Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812049963/su2538Isup3.cml

checkCIF report

Comment top

In the course of our study on selective electrophilic aromatic aroylation of 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 structure of 1,8-diaroyled 2,7-dimethoxynaphthalene derivatives such as 1,8-bis(4-aminobenzoyl)-2,7-dimethoxynaphthalene (Nishijima et al., 2010), [8-(4-butoxybenzoyl)-2,7-dimethoxynaphthalen-1-yl](4-butoxyphenyl)methanone [1,8-bis(4-butoxybenzoyl)-2,7-dimethoxynaphthalene] (Sasagawa et al., 2011), [2,7-dimethoxy-8-(2-naphthoyl)naphthalene-1-yl](naphthalene-2-yl)methanone [2,7-dimethoxy-1,8-bis(2-naphthoyl)naphthalene] (Tsumuki et al., 2011), and (3,5-dimethylphenyl)[8-(3,5-dimethylbenzoyl)-2,7-dimethoxynaphthalen-1-yl]methanone (Muto et al., 2012). The simplest molecule in these analogues, 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008), lies across a crystallographic 2-fold axis and the molecular packing is stabilized by C—H···O interactions between carbonyl groups and benzene ring and π···π interactions between benzene rings. 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, is reported on herein.

The molecule structure of the title molecule is illustrated in Fig. 1. The two benzoyl groups are situated in an (anti)-orientation and twisted away from the attached naphthalene ring. The dihedral angle between the planes of the two benzene rings (C12-C17 & C19-C24) is 20.03 (7)°. The dihedral angles between these benzene rings and the naphthalene (C1-C10) ring are 68.42 (5)° and 71.69 (5)°. These dihedral angles are similar to that reported for 1,8-dibenzoyl-2,7-dimethoxynaphthalene [80.25 (6)°; Nakaema et al., 2008]. The torsion angles between the carbonyl groups and the naphthalene ring are -63.28 (14)° [C9—C1—C11—O3] and -66.19 (14)° [C9—C8—C18—O4]. The C═O groups lie almost in the plane of the attached benzene ring with torsion angles equal to 1.58 (17)° [O3—C11—C12—C17] and 1.44 (17)° [O4—C18—C19—C24].

In the crystal, the molecular packing of the title compound is mainly stabilized by two types of C—H···O interactions involving adjacent molecules and leading to the formation of chains along the a axis (Table 1 and Fig. 2).

Related literature top

For electrophilic aroylation of naphthalene derivatives, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011). For the structures of closely related compounds, see: Nakaema et al. (2008); Nishijima et al. (2010); Sasagawa et al. (2011); Tsumuki et al. (2011); Muto et al. (2012).

Experimental top

To a 100 ml flask, benzoyl chloride (422 mg, 3.0 mmol), titanium chloride (1.71 g, 9.0 mmol) and methylene chloride (1.5 ml) were stirred at 298 K under nitrogen atmosphere. To reaction mixture thus obtained, 2,7-diethoxynaphtharene (216 mg, 1.0 mmol) and methylene chloride (1.0 ml) were added. After the reaction mixture was stirred at r.t. for 24 h, it was poured into ice-cold water (20 ml). The aqueous layer was extracted with CHCl₃ (10 ml × 3). The combined extracts were washed with 2 M 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. The crude product was purified by recrystallization from CHCl₃/methanol (1: 2 v/v) solution (81% yield). Colorless platelet single crystals suitable for X-ray diffraction were obtained by repeated crystallization from a CHCl₃/ methanol (1:2 v/v) solution (52% yield). Anal. Calcd for C₂₈H₂₄O₄: C 79.22, H5.70. Found: C 79.32, H 5.84.; M.p. = 467–468 K. Spectroscopic data for the title compound are available in the archived CIF.

Structure description top

For electrophilic aroylation of naphthalene derivatives, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011). For the structures of closely related compounds, see: Nakaema et al. (2008); Nishijima et al. (2010); Sasagawa et al. (2011); Tsumuki et al. (2011); Muto et al. (2012).

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 of the title molecule, with atom numbering. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial view of the crystal packing of the title compound, showing the intermolecular C-H···O hydrogen bonds (see Table 1 for details; symmetry codes: (i) x+1, y, z; (ii) x-1, y, z).

(8-Benzoyl-2,7-diethoxynaphthalen-1-yl)(phenyl)methanone top

Crystal data top

C₂₈H₂₄O₄	F(000) = 896
M_r = 424.47	D_x = 1.260 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2yn	Cell parameters from 37233 reflections
a = 7.92185 (14) Å	θ = 3.2–68.3°
b = 20.6794 (4) Å	µ = 0.67 mm⁻¹
c = 14.2130 (3) Å	T = 193 K
β = 106.043 (1)°	Needle, colourless
V = 2237.68 (7) Å³	0.60 × 0.50 × 0.10 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4076 independent reflections
Radiation source: fine-focus sealed tube	3736 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 10.000 pixels mm^-1	θ_max = 68.2°, θ_min = 3.9°
ω scans	h = −9→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −24→24
T_min = 0.689, T_max = 0.936	l = −17→17
39782 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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0439P)² + 0.5163P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4076 reflections	Δρ_max = 0.23 e Å⁻³
292 parameters	Δρ_min = −0.16 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: 0.0075 (3)

Crystal data top

C₂₈H₂₄O₄	V = 2237.68 (7) Å³
M_r = 424.47	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 7.92185 (14) Å	µ = 0.67 mm⁻¹
b = 20.6794 (4) Å	T = 193 K
c = 14.2130 (3) Å	0.60 × 0.50 × 0.10 mm
β = 106.043 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4076 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	3736 reflections with I > 2σ(I)
T_min = 0.689, T_max = 0.936	R_int = 0.041
39782 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.05	Δρ_max = 0.23 e Å⁻³
4076 reflections	Δρ_min = −0.16 e Å⁻³
292 parameters

Special details top

Experimental. Spectroscopic data for the title compound: ¹H NMR δ (300 MHz, CDCl₃); 0.91 (6H, t, J = 6.9 Hz), 3.95 (4H, q, J = 6.9 Hz), 7.16 (2H, d, J = 9.0 Hz), 7.35 (4H, t, J = 7.2 Hz), 7.49(2H, t, J = 7.2 Hz), 7.73 (4H, d, J = 7.2 Hz), 7.91 (2H, d, J = 9.0 Hz) p.p.m.; ¹³C NMR δ (75 MHz, CDCl₃); 13.92, 64.42, 111.89, 121.27, 125.05, 127.43, 128.54, 129.80, 131.79, 131.95, 138.93, 155.52, 197.04 p.p.m.; IR (KBr, cm^-1): 1665 (C═ O), 1612, 1510, 1452 (Ar), 1266 (═C—O—C).

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	0.29349 (11)	0.08669 (4)	1.04839 (6)	0.0381 (2)
O2	−0.21634 (12)	0.01858 (4)	0.55669 (6)	0.0458 (2)
O3	−0.02728 (10)	0.16304 (4)	0.86895 (6)	0.0383 (2)
O4	0.08625 (10)	0.12983 (4)	0.66958 (6)	0.0414 (2)
C1	0.12835 (13)	0.06508 (5)	0.88895 (8)	0.0299 (2)
C2	0.21642 (14)	0.04134 (5)	0.98017 (8)	0.0325 (3)
C3	0.21668 (15)	−0.02515 (6)	1.00229 (9)	0.0367 (3)
H3	0.2781	−0.0406	1.0654	0.044*
C4	0.12768 (15)	−0.06697 (6)	0.93199 (9)	0.0375 (3)
H4	0.1268	−0.1117	0.9471	0.045*
C5	−0.05370 (16)	−0.08988 (6)	0.76527 (10)	0.0398 (3)
H5	−0.0536	−0.1344	0.7817	0.048*
C6	−0.14091 (16)	−0.07056 (6)	0.67303 (9)	0.0410 (3)
H6	−0.2012	−0.1012	0.6258	0.049*
C7	−0.14038 (15)	−0.00448 (6)	0.64861 (9)	0.0361 (3)
C8	−0.05794 (14)	0.04132 (5)	0.71690 (8)	0.0314 (2)
C9	0.03474 (13)	0.02192 (5)	0.81381 (8)	0.0302 (2)
C10	0.03651 (14)	−0.04555 (5)	0.83711 (9)	0.0341 (3)
C11	0.11515 (14)	0.13756 (5)	0.87770 (8)	0.0299 (2)
C12	0.27340 (14)	0.17695 (5)	0.87977 (8)	0.0320 (2)
C13	0.43562 (15)	0.14857 (6)	0.88777 (9)	0.0390 (3)
H13	0.4468	0.1028	0.8910	0.047*
C14	0.58108 (16)	0.18650 (7)	0.89110 (10)	0.0477 (3)
H14	0.6918	0.1668	0.8966	0.057*
C15	0.56497 (18)	0.25260 (7)	0.88645 (11)	0.0542 (4)
H15	0.6650	0.2787	0.8893	0.065*
C16	0.4039 (2)	0.28145 (7)	0.87758 (13)	0.0586 (4)
H16	0.3933	0.3272	0.8739	0.070*
C17	0.25816 (17)	0.24361 (6)	0.87402 (11)	0.0455 (3)
H17	0.1474	0.2634	0.8676	0.055*
C18	−0.05219 (14)	0.10942 (5)	0.67903 (8)	0.0310 (2)
C19	−0.21431 (14)	0.14952 (5)	0.65338 (8)	0.0310 (2)
C20	−0.37066 (15)	0.12789 (6)	0.66818 (9)	0.0390 (3)
H20	−0.3762	0.0860	0.6947	0.047*
C21	−0.51890 (16)	0.16678 (7)	0.64465 (10)	0.0459 (3)
H21	−0.6257	0.1516	0.6547	0.055*
C22	−0.51078 (18)	0.22760 (7)	0.60655 (10)	0.0483 (3)
H22	−0.6126	0.2541	0.5898	0.058*
C23	−0.35529 (19)	0.25015 (7)	0.59266 (11)	0.0531 (4)
H23	−0.3498	0.2924	0.5673	0.064*
C24	−0.20769 (17)	0.21117 (6)	0.61576 (10)	0.0435 (3)
H24	−0.1010	0.2267	0.6058	0.052*
C25	0.42914 (16)	0.06661 (6)	1.13328 (9)	0.0420 (3)
H25A	0.5139	0.0379	1.1140	0.050*
H25B	0.3777	0.0429	1.1792	0.050*
C26	0.5191 (2)	0.12683 (7)	1.18056 (11)	0.0571 (4)
H26A	0.4357	0.1534	1.2032	0.068*
H26B	0.5624	0.1513	1.1329	0.068*
H26C	0.6181	0.1151	1.2365	0.068*
C27	−0.26626 (18)	−0.02602 (7)	0.47696 (9)	0.0469 (3)
H27A	−0.3661	−0.0530	0.4830	0.056*
H27B	−0.1667	−0.0549	0.4766	0.056*
C28	−0.31808 (19)	0.01303 (7)	0.38490 (10)	0.0515 (3)
H28A	−0.2205	0.0413	0.3817	0.062*
H28B	−0.4211	0.0394	0.3844	0.062*
H28C	−0.3465	−0.0160	0.3282	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0391 (4)	0.0380 (4)	0.0334 (4)	0.0027 (3)	0.0035 (3)	0.0007 (3)
O2	0.0568 (6)	0.0368 (5)	0.0362 (5)	0.0032 (4)	−0.0001 (4)	−0.0053 (4)
O3	0.0266 (4)	0.0375 (4)	0.0499 (5)	0.0040 (3)	0.0094 (4)	−0.0037 (4)
O4	0.0306 (4)	0.0456 (5)	0.0502 (5)	−0.0024 (3)	0.0149 (4)	0.0054 (4)
C1	0.0243 (5)	0.0317 (6)	0.0356 (6)	0.0007 (4)	0.0114 (4)	0.0011 (4)
C2	0.0275 (5)	0.0355 (6)	0.0355 (6)	0.0016 (4)	0.0105 (5)	−0.0005 (5)
C3	0.0343 (6)	0.0389 (6)	0.0372 (6)	0.0056 (5)	0.0103 (5)	0.0077 (5)
C4	0.0375 (6)	0.0304 (6)	0.0463 (7)	0.0036 (5)	0.0146 (5)	0.0069 (5)
C5	0.0424 (7)	0.0278 (6)	0.0502 (7)	0.0005 (5)	0.0146 (6)	−0.0009 (5)
C6	0.0421 (7)	0.0326 (6)	0.0463 (7)	−0.0014 (5)	0.0090 (6)	−0.0082 (5)
C7	0.0335 (6)	0.0362 (6)	0.0376 (6)	0.0029 (5)	0.0081 (5)	−0.0026 (5)
C8	0.0271 (5)	0.0310 (6)	0.0371 (6)	0.0027 (4)	0.0104 (5)	−0.0006 (5)
C9	0.0252 (5)	0.0309 (5)	0.0366 (6)	0.0017 (4)	0.0120 (4)	0.0006 (4)
C10	0.0314 (6)	0.0305 (6)	0.0423 (7)	0.0022 (4)	0.0136 (5)	0.0014 (5)
C11	0.0263 (5)	0.0336 (6)	0.0288 (5)	0.0019 (4)	0.0059 (4)	−0.0014 (4)
C12	0.0286 (6)	0.0341 (6)	0.0316 (6)	−0.0007 (4)	0.0054 (4)	0.0023 (4)
C13	0.0304 (6)	0.0393 (6)	0.0472 (7)	0.0021 (5)	0.0104 (5)	0.0066 (5)
C14	0.0273 (6)	0.0594 (8)	0.0551 (8)	−0.0003 (5)	0.0090 (6)	0.0139 (7)
C15	0.0394 (7)	0.0570 (9)	0.0628 (9)	−0.0168 (6)	0.0085 (6)	0.0119 (7)
C16	0.0539 (8)	0.0367 (7)	0.0840 (11)	−0.0087 (6)	0.0171 (8)	0.0089 (7)
C17	0.0377 (7)	0.0362 (7)	0.0616 (8)	0.0017 (5)	0.0119 (6)	0.0057 (6)
C18	0.0291 (5)	0.0345 (6)	0.0291 (6)	−0.0020 (4)	0.0077 (4)	−0.0019 (4)
C19	0.0307 (6)	0.0317 (6)	0.0295 (6)	−0.0002 (4)	0.0065 (4)	−0.0018 (4)
C20	0.0327 (6)	0.0339 (6)	0.0501 (7)	−0.0020 (5)	0.0110 (5)	−0.0004 (5)
C21	0.0296 (6)	0.0488 (7)	0.0579 (8)	0.0000 (5)	0.0097 (6)	−0.0075 (6)
C22	0.0419 (7)	0.0497 (8)	0.0476 (8)	0.0163 (6)	0.0030 (6)	−0.0005 (6)
C23	0.0581 (8)	0.0433 (7)	0.0585 (9)	0.0130 (6)	0.0173 (7)	0.0170 (6)
C24	0.0419 (7)	0.0410 (7)	0.0498 (8)	0.0018 (5)	0.0162 (6)	0.0098 (6)
C25	0.0373 (6)	0.0481 (7)	0.0360 (6)	0.0040 (5)	0.0026 (5)	0.0033 (5)
C26	0.0538 (8)	0.0551 (9)	0.0504 (8)	−0.0017 (7)	−0.0055 (7)	−0.0013 (7)
C27	0.0516 (8)	0.0469 (7)	0.0394 (7)	−0.0044 (6)	0.0082 (6)	−0.0101 (6)
C28	0.0513 (8)	0.0602 (9)	0.0406 (7)	−0.0046 (6)	0.0091 (6)	−0.0049 (6)

Geometric parameters (Å, º) top

O1—C2	1.3657 (14)	C15—C16	1.382 (2)
O1—C25	1.4374 (14)	C15—H15	0.9500
O2—C7	1.3645 (15)	C16—C17	1.3841 (18)
O2—C27	1.4297 (15)	C16—H16	0.9500
O3—C11	1.2201 (13)	C17—H17	0.9500
O4—C18	1.2167 (13)	C18—C19	1.4870 (15)
C1—C2	1.3815 (16)	C19—C20	1.3865 (16)
C1—C9	1.4315 (15)	C19—C24	1.3890 (17)
C1—C11	1.5079 (15)	C20—C21	1.3858 (17)
C2—C3	1.4104 (16)	C20—H20	0.9500
C3—C4	1.3616 (17)	C21—C22	1.378 (2)
C3—H3	0.9500	C21—H21	0.9500
C4—C10	1.4135 (17)	C22—C23	1.381 (2)
C4—H4	0.9500	C22—H22	0.9500
C5—C6	1.3620 (18)	C23—C24	1.3830 (18)
C5—C10	1.4108 (17)	C23—H23	0.9500
C5—H5	0.9500	C24—H24	0.9500
C6—C7	1.4101 (17)	C25—C26	1.4985 (19)
C6—H6	0.9500	C25—H25A	0.9900
C7—C8	1.3839 (16)	C25—H25B	0.9900
C8—C9	1.4277 (16)	C26—H26A	0.9800
C8—C18	1.5129 (15)	C26—H26B	0.9800
C9—C10	1.4331 (15)	C26—H26C	0.9800
C11—C12	1.4886 (15)	C27—C28	1.4952 (19)
C12—C17	1.3842 (17)	C27—H27A	0.9900
C12—C13	1.3886 (15)	C27—H27B	0.9900
C13—C14	1.3839 (17)	C28—H28A	0.9800
C13—H13	0.9500	C28—H28B	0.9800
C14—C15	1.373 (2)	C28—H28C	0.9800
C14—H14	0.9500

C2—O1—C25	118.78 (9)	C17—C16—H16	120.0
C7—O2—C27	119.05 (10)	C16—C17—C12	120.17 (12)
C2—C1—C9	120.12 (10)	C16—C17—H17	119.9
C2—C1—C11	117.05 (10)	C12—C17—H17	119.9
C9—C1—C11	122.29 (10)	O4—C18—C19	121.56 (10)
O1—C2—C1	115.67 (10)	O4—C18—C8	118.61 (10)
O1—C2—C3	122.57 (10)	C19—C18—C8	119.83 (9)
C1—C2—C3	121.66 (11)	C20—C19—C24	119.00 (11)
C4—C3—C2	119.15 (11)	C20—C19—C18	122.01 (10)
C4—C3—H3	120.4	C24—C19—C18	118.96 (10)
C2—C3—H3	120.4	C21—C20—C19	120.60 (11)
C3—C4—C10	121.70 (11)	C21—C20—H20	119.7
C3—C4—H4	119.1	C19—C20—H20	119.7
C10—C4—H4	119.1	C22—C21—C20	119.74 (12)
C6—C5—C10	121.79 (11)	C22—C21—H21	120.1
C6—C5—H5	119.1	C20—C21—H21	120.1
C10—C5—H5	119.1	C21—C22—C23	120.31 (12)
C5—C6—C7	119.08 (11)	C21—C22—H22	119.8
C5—C6—H6	120.5	C23—C22—H22	119.8
C7—C6—H6	120.5	C22—C23—C24	119.87 (12)
O2—C7—C8	115.47 (10)	C22—C23—H23	120.1
O2—C7—C6	122.95 (11)	C24—C23—H23	120.1
C8—C7—C6	121.56 (11)	C23—C24—C19	120.46 (12)
C7—C8—C9	120.10 (10)	C23—C24—H24	119.8
C7—C8—C18	116.25 (10)	C19—C24—H24	119.8
C9—C8—C18	123.15 (10)	O1—C25—C26	106.80 (10)
C8—C9—C1	124.53 (10)	O1—C25—H25A	110.4
C8—C9—C10	117.78 (10)	C26—C25—H25A	110.4
C1—C9—C10	117.69 (10)	O1—C25—H25B	110.4
C5—C10—C4	120.66 (11)	C26—C25—H25B	110.4
C5—C10—C9	119.65 (11)	H25A—C25—H25B	108.6
C4—C10—C9	119.69 (11)	C25—C26—H26A	109.5
O3—C11—C12	121.04 (10)	C25—C26—H26B	109.5
O3—C11—C1	118.37 (9)	H26A—C26—H26B	109.5
C12—C11—C1	120.57 (9)	C25—C26—H26C	109.5
C17—C12—C13	119.30 (11)	H26A—C26—H26C	109.5
C17—C12—C11	118.99 (10)	H26B—C26—H26C	109.5
C13—C12—C11	121.71 (10)	O2—C27—C28	107.10 (11)
C14—C13—C12	120.42 (12)	O2—C27—H27A	110.3
C14—C13—H13	119.8	C28—C27—H27A	110.3
C12—C13—H13	119.8	O2—C27—H27B	110.3
C15—C14—C13	119.82 (12)	C28—C27—H27B	110.3
C15—C14—H14	120.1	H27A—C27—H27B	108.5
C13—C14—H14	120.1	C27—C28—H28A	109.5
C14—C15—C16	120.36 (12)	C27—C28—H28B	109.5
C14—C15—H15	119.8	H28A—C28—H28B	109.5
C16—C15—H15	119.8	C27—C28—H28C	109.5
C15—C16—C17	119.93 (13)	H28A—C28—H28C	109.5
C15—C16—H16	120.0	H28B—C28—H28C	109.5

C25—O1—C2—C1	−161.30 (10)	C2—C1—C11—O3	−108.29 (12)
C25—O1—C2—C3	22.47 (15)	C9—C1—C11—O3	63.28 (14)
C9—C1—C2—O1	−176.52 (9)	C2—C1—C11—C12	70.21 (13)
C11—C1—C2—O1	−4.75 (14)	C9—C1—C11—C12	−118.21 (11)
C9—C1—C2—C3	−0.25 (16)	O3—C11—C12—C17	1.58 (17)
C11—C1—C2—C3	171.51 (10)	C1—C11—C12—C17	−176.88 (11)
O1—C2—C3—C4	175.92 (10)	O3—C11—C12—C13	−178.72 (11)
C1—C2—C3—C4	−0.08 (16)	C1—C11—C12—C13	2.81 (16)
C2—C3—C4—C10	0.64 (17)	C17—C12—C13—C14	0.74 (19)
C10—C5—C6—C7	0.25 (18)	C11—C12—C13—C14	−178.95 (11)
C27—O2—C7—C8	164.97 (11)	C12—C13—C14—C15	0.0 (2)
C27—O2—C7—C6	−13.53 (17)	C13—C14—C15—C16	−0.6 (2)
C5—C6—C7—O2	176.45 (11)	C14—C15—C16—C17	0.4 (2)
C5—C6—C7—C8	−1.97 (18)	C15—C16—C17—C12	0.3 (2)
O2—C7—C8—C9	−176.28 (9)	C13—C12—C17—C16	−0.9 (2)
C6—C7—C8—C9	2.25 (17)	C11—C12—C17—C16	178.82 (13)
O2—C7—C8—C18	−4.12 (14)	C7—C8—C18—O4	−105.71 (12)
C6—C7—C8—C18	174.41 (10)	C9—C8—C18—O4	66.19 (14)
C7—C8—C9—C1	178.17 (10)	C7—C8—C18—C19	73.69 (13)
C18—C8—C9—C1	6.58 (16)	C9—C8—C18—C19	−114.42 (12)
C7—C8—C9—C10	−0.83 (15)	O4—C18—C19—C20	−176.90 (11)
C18—C8—C9—C10	−172.42 (9)	C8—C18—C19—C20	3.72 (16)
C2—C1—C9—C8	−178.97 (10)	O4—C18—C19—C24	1.44 (17)
C11—C1—C9—C8	9.71 (16)	C8—C18—C19—C24	−177.94 (11)
C2—C1—C9—C10	0.03 (14)	C24—C19—C20—C21	0.84 (18)
C11—C1—C9—C10	−171.29 (9)	C18—C19—C20—C21	179.18 (11)
C6—C5—C10—C4	−179.28 (11)	C19—C20—C21—C22	−0.3 (2)
C6—C5—C10—C9	1.12 (17)	C20—C21—C22—C23	−0.6 (2)
C3—C4—C10—C5	179.54 (11)	C21—C22—C23—C24	0.9 (2)
C3—C4—C10—C9	−0.86 (17)	C22—C23—C24—C19	−0.3 (2)
C8—C9—C10—C5	−0.82 (15)	C20—C19—C24—C23	−0.53 (19)
C1—C9—C10—C5	−179.89 (10)	C18—C19—C24—C23	−178.92 (12)
C8—C9—C10—C4	179.57 (10)	C2—O1—C25—C26	165.89 (11)
C1—C9—C10—C4	0.50 (15)	C7—O2—C27—C28	−171.15 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3ⁱ	0.95	2.37	3.2404 (16)	153
C21—H21···O4ⁱⁱ	0.95	2.39	3.3326 (16)	171

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₄O₄
M_r	424.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	193
a, b, c (Å)	7.92185 (14), 20.6794 (4), 14.2130 (3)
β (°)	106.043 (1)
V (Å³)	2237.68 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.67
Crystal size (mm)	0.60 × 0.50 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.689, 0.936
No. of measured, independent and observed [I > 2σ(I)] reflections	39782, 4076, 3736
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.091, 1.05
No. of reflections	4076
No. of parameters	292
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.16

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

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3ⁱ	0.95	2.37	3.2404 (16)	153
C21—H21···O4ⁱⁱ	0.95	2.39	3.3326 (16)	171

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

Acknowledgements

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

References

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