[2,7-Dimeth­oxy-8-(2-naphtho­yl)naphthalen-1-yl](naphthalen-2-yl)methanone

Tsumuki, T.; Hijikata, D.; Okamoto, A.; Oike, H.; Yonezawa, N.

doi:10.1107/S1600536811028054

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2095

doi:10.1107/S1600536811028054

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[2,7-Dimethoxy-8-(2-naphthoyl)naphthalen-1-yl](naphthalen-2-yl)methanone

Takehiro Tsumuki,^a Daichi Hijikata,^a Akiko Okamoto,^a ^* Hideaki Oike ^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 12 July 2011; accepted 13 July 2011; online 23 July 2011)

The molecule of the title compound, C₃₄H₂₄O₄, possesses crystallographically imposed twofold C₂ symmetry. The two 2-naphthoyl groups at the 1- and 8-positions of the central naphthalene ring are aligned almost antiparallel [5.21 (5)°]. The dihedral angle between the central 2,7-dimethoxynaphthalene unit and the terminal naphthyl groups is 75.13 (4)°. In the crystal, weak C—H⋯O hydrogen bonds and π–π stacking interactions [centroid–centroid and interplanar distances are 3.6486 (8) and 3.3734 (5) Å, respectively] are observed.

Related literature

For the electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene giving aroylated naphthalene compounds, see: Okamoto & Yonezawa (2009 ). For the structures of closely related compounds, see: Hijikata et al. (2010 ); Muto et al. (2010 ); Nakaema et al. (2008 ); Nishijima et al. (2010 ).

Experimental

Crystal data

C₃₄H₂₄O₄
M_r = 496.53
Monoclinic, C 2/c
a = 12.8325 (5) Å
b = 12.2459 (4) Å
c = 15.8798 (6) Å
β = 97.618 (1)°
V = 2473.41 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 193 K
0.50 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.958, T_max = 0.983
19645 measured reflections
2832 independent reflections
2370 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.115
S = 1.11
2832 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.28 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
C3ⁱ—H3ⁱ⋯O1	0.95	2.59	3.3795 (17)	141
C16ⁱⁱ—H16ⁱⁱ⋯O1	0.95	2.49	3.4382 (14)	175
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y, z-{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811028054/rz2628sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811028054/rz2628Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811028054/rz2628Isup3.cml

checkCIF report

Comment top

In the course of our study on electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have been found to be formed regioselectively with the aid of suitable acidic mediators (Okamoto & Yonezawa, 2009). We have reported the X-ray crystal structures of 1,8-diaroylated 2,7-dimethoxynaphthalenes such as 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008), 1,8-bis(4-methylbenzoyl)-2,7-dimethoxynaphthalene (Muto et al., 2010) and 1,8-bis(4-aminobenzoyl)-2,7-dimethoxynaphthalene (Nishijima et al., 2010). The aromatic rings in these types of molecules are generally assembled with non-coplanar configuration. In these compounds, two aroyl groups tend to attach in nearly perpendicular manner and orient in opposite direction. Recently, the crystal structure of 2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene has been clarified as syn-conformation, where two phenoxybenzoyl groups are oriented in the same direction (Hijikata et al., 2010). As a part of our continuous studies on the molecular structures of homologous aroylated 2,7-dimethoxynaphthalene molecules, the X-ray crystal structure of the title compound, (I), bis(2-naphthoylated) 2,7-dimethoxynaphthalene, is discussed in this article.

An ORTEPIII (Burnett & Johnson, 1996) plot of the title compound is displayed in Fig. 1. The molecule of (I) lies across a crystallographic 2-fold axis so that the asymmetric unit contains one-half of the molecule. Thus, the two terminal naphthoyl groups are situated in anti orientation. The dihedral angle between the central 2,7-dimethoxynaphthalene ring (C1–C6 and C1ⁱ–C4ⁱ) and the terminal naphthyl groups (C8–C17) is 75.13 (4)°. The torsion angles of the central 2,7-dimethoxynaphthalene moiety (C1–C6 and C1ⁱ–C4ⁱ) and the terminal naphthyl group (C8–C17) with the carbonyl group (C7–O1) are -66.78 (14) [C6—C1—C7—O1] and -179.50 (11)° [O1—C7—C8—C17], respectively.

In the crystal, an oxygen atom of the carbonyl group form two types of intermolecular C—H···O hydrogen bonds with the naphthalene ring hydrogen of the central 2,7-dimethoxynaphthalene moiety [C3—H3···O1 = 2.59 Å] and that of the terminal naphthoyl group [C16—H16···O1 = 2.49 Å], respectively (Table 1 and Fig. 2). Furthermore, an intermolecular π—π stacking interaction is observed between naphthalene rings of the terminal naphthoyl group (C8–C17) with that of the adjacent molecule along the a axis [centroid—centroid and interplanar distances are 3.6486 (8) and 3.3734 (5) Å, respectively] (Fig. 3).

Related literature top

For the electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene giving aroylated naphthalene compounds, see: Okamoto & Yonezawa (2009). For the structures of closely related compounds, see: Hijikata et al. (2010); Muto et al. (2010); Nakaema et al. (2008); Nishijima et al. (2010).

Experimental top

To a solution of 2-naphthoyl chloride (629.1 mg, 3.3 mmol) and TiCl₄ (1802.0 mg, 9.5 mmol) in CH₂Cl₂ (2.5 ml), 2,7-dimethoxynaphthalene (188.2 mg, 1.0 mmol) was added. The reaction mixture was stirred at r.t. for 3 h, then poured into ice-cold water (10 ml) and the aqueous layer was extracted with CHCl₃ (5 ml × 3). The combined organic extracts were washed with 2 M aqueous NaOH (20 ml × 3) followed by washing with brine (20 ml × 3). The organic layer was dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give a cake (72% yield). The crude product was purified by recrystallization from acetone (22% isolated yield). Furthermore, the isolated product was crystallized from acetone to give single crystals suitable for X-ray amalysis.

Spectroscopic data: ¹H NMR (300 MHz, CDCl₃) δ 3.67 (6H, s), 7.26 (2H, d, J = 9.0 Hz), 7.37 (2H, t, J = 7.5 Hz), 7.45 (2H, t, J = 7.5 Hz), 7.68–7.77 (8H, m), 8.03 (2H, d, J = 9.0 Hz), 8.09 (2H, brs) p.p.m.; ¹³C NMR (75 MHz, CDCl₃) δ 56.47, 111.38, 121.73, 124.75, 125.64, 125.92, 127.54, 127.60, 127.83, 129.62, 130.16, 131.11, 132.17, 132.40, 135.50, 136.05, 156.52, 196.66 p.p.m.; IR (KBr):1660(C=O), 1624(Ar), 1510(Ar), 1258(OMe) cm^-1; HRMS (m/z):[M + H]⁺ calcd. for C₃₄H₂₅O₄, 497.1753; found, 497.1751; m.p. = 505.0–506.0 K

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of compound (I). Displacement ellipsoids are drawn at the 50% probability level. Symmetry code: (i) -x+1, y, -z+1/2.
	Fig. 2. A partial packing diagram of compound (I), showing the C3—H3···O1 (blue dashed lines) and C16—H16···O1 (red dashed lines) hydrogen interactions. Symmetry codes: (i) 1-x, y, 1/2-z; (ii) 3/2-x, 1/2+y 1/2-z; (iii) x, -y, 1/2+z; (iv) 1-x, -y, 1-z; (v) 3/2-x, 1/2-y, 1-z; (vi) 1/2+x, 1/2-y, 1/2+z; (vii) 1/2+x, 1/2+y, z.
	Fig. 3. Side view of the π—π stacking interactions (dashed lines). Cg4 is the centroid of the C10–C15 ring.

[2,7-Dimethoxy-8-(2-naphthoyl)naphthalen-1-yl](naphthalen-2-yl)methanone top

Crystal data top

C₃₄H₂₄O₄	F(000) = 1040
M_r = 496.53	D_x = 1.333 Mg m⁻³
Monoclinic, C2/c	Melting point = 505.0–506.0 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71075 Å
a = 12.8325 (5) Å	Cell parameters from 14952 reflections
b = 12.2459 (4) Å	θ = 3.2–27.4°
c = 15.8798 (6) Å	µ = 0.09 mm⁻¹
β = 97.618 (1)°	T = 193 K
V = 2473.41 (16) Å³	Block, colorless
Z = 4	0.50 × 0.20 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2832 independent reflections
Radiation source: rotating anode	2370 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.4°, θ_min = 3.2°
ω scans	h = −16→16
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −15→15
T_min = 0.958, T_max = 0.983	l = −20→20
19645 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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.059P)² + 1.0486P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
2832 reflections	Δρ_max = 0.28 e Å⁻³
175 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: 0.0039 (6)

Crystal data top

C₃₄H₂₄O₄	V = 2473.41 (16) Å³
M_r = 496.53	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 12.8325 (5) Å	µ = 0.09 mm⁻¹
b = 12.2459 (4) Å	T = 193 K
c = 15.8798 (6) Å	0.50 × 0.20 × 0.20 mm
β = 97.618 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2832 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2370 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.983	R_int = 0.022
19645 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.11	Δρ_max = 0.28 e Å⁻³
2832 reflections	Δρ_min = −0.18 e Å⁻³
175 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	0.61538 (7)	−0.01315 (7)	0.20166 (5)	0.0321 (2)
O2	0.77075 (7)	0.14496 (8)	0.34570 (7)	0.0453 (3)
C1	0.59528 (9)	0.14332 (9)	0.28387 (7)	0.0255 (2)
C2	0.68212 (9)	0.20368 (10)	0.31776 (8)	0.0325 (3)
C3	0.68048 (11)	0.31884 (11)	0.31852 (9)	0.0389 (3)
H3	0.7405	0.3590	0.3426	0.047*
C4	0.59161 (11)	0.37129 (10)	0.28429 (8)	0.0374 (3)
H4	0.5910	0.4489	0.2834	0.045*
C5	0.5000	0.31424 (13)	0.2500	0.0299 (3)
C6	0.5000	0.19760 (12)	0.2500	0.0243 (3)
C7	0.61088 (8)	0.02168 (9)	0.27324 (7)	0.0245 (2)
C8	0.61793 (8)	−0.05224 (9)	0.34796 (7)	0.0254 (2)
C9	0.62457 (9)	−0.16296 (9)	0.33478 (7)	0.0272 (3)
H9	0.6299	−0.1895	0.2793	0.033*
C10	0.62360 (9)	−0.23787 (9)	0.40247 (7)	0.0273 (3)
C11	0.62992 (11)	−0.35233 (10)	0.39025 (8)	0.0351 (3)
H11	0.6371	−0.3803	0.3355	0.042*
C12	0.62582 (11)	−0.42292 (11)	0.45670 (9)	0.0401 (3)
H12	0.6293	−0.4994	0.4476	0.048*
C13	0.61644 (11)	−0.38257 (11)	0.53837 (9)	0.0392 (3)
H13	0.6133	−0.4321	0.5840	0.047*
C14	0.61188 (10)	−0.27273 (12)	0.55253 (8)	0.0360 (3)
H14	0.6063	−0.2466	0.6081	0.043*
C15	0.61532 (9)	−0.19709 (10)	0.48511 (7)	0.0281 (3)
C16	0.61118 (10)	−0.08247 (10)	0.49767 (7)	0.0316 (3)
H16	0.6079	−0.0544	0.5530	0.038*
C17	0.61192 (9)	−0.01221 (10)	0.43099 (7)	0.0295 (3)
H17	0.6084	0.0643	0.4403	0.035*
C18	0.85102 (12)	0.19798 (14)	0.40216 (10)	0.0513 (4)
H18A	0.9065	0.1454	0.4217	0.062*
H18B	0.8208	0.2268	0.4511	0.062*
H18C	0.8808	0.2581	0.3724	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0388 (5)	0.0320 (4)	0.0255 (4)	0.0067 (4)	0.0041 (3)	0.0003 (3)
O2	0.0253 (5)	0.0440 (5)	0.0631 (6)	−0.0035 (4)	−0.0073 (4)	−0.0025 (5)
C1	0.0250 (5)	0.0252 (5)	0.0265 (5)	−0.0019 (4)	0.0042 (4)	0.0006 (4)
C2	0.0275 (6)	0.0333 (6)	0.0364 (6)	−0.0044 (5)	0.0030 (5)	−0.0011 (5)
C3	0.0376 (7)	0.0343 (7)	0.0442 (7)	−0.0140 (5)	0.0035 (6)	−0.0053 (5)
C4	0.0492 (8)	0.0230 (6)	0.0408 (7)	−0.0078 (5)	0.0087 (6)	−0.0024 (5)
C5	0.0376 (9)	0.0231 (8)	0.0300 (8)	0.000	0.0077 (7)	0.000
C6	0.0280 (8)	0.0216 (7)	0.0238 (7)	0.000	0.0056 (6)	0.000
C7	0.0194 (5)	0.0265 (5)	0.0272 (5)	0.0011 (4)	0.0014 (4)	0.0000 (4)
C8	0.0220 (5)	0.0276 (6)	0.0260 (5)	0.0026 (4)	0.0014 (4)	0.0002 (4)
C9	0.0272 (5)	0.0300 (6)	0.0242 (5)	0.0017 (4)	0.0024 (4)	−0.0018 (4)
C10	0.0244 (5)	0.0278 (6)	0.0292 (6)	0.0008 (4)	0.0016 (4)	0.0010 (4)
C11	0.0415 (7)	0.0289 (6)	0.0346 (6)	−0.0008 (5)	0.0040 (5)	−0.0009 (5)
C12	0.0431 (7)	0.0299 (6)	0.0465 (8)	−0.0007 (5)	0.0026 (6)	0.0058 (5)
C13	0.0375 (7)	0.0413 (7)	0.0383 (7)	−0.0023 (5)	0.0029 (5)	0.0140 (5)
C14	0.0330 (6)	0.0460 (7)	0.0294 (6)	0.0007 (5)	0.0052 (5)	0.0063 (5)
C15	0.0231 (5)	0.0348 (6)	0.0263 (5)	0.0023 (4)	0.0024 (4)	0.0018 (5)
C16	0.0331 (6)	0.0374 (6)	0.0242 (5)	0.0048 (5)	0.0040 (4)	−0.0031 (5)
C17	0.0303 (6)	0.0291 (6)	0.0286 (6)	0.0048 (4)	0.0021 (4)	−0.0037 (5)
C18	0.0336 (7)	0.0641 (10)	0.0521 (8)	−0.0117 (7)	−0.0094 (6)	0.0046 (7)

Geometric parameters (Å, º) top

O1—C7	1.2226 (13)	C9—H9	0.9500
O2—C2	1.3689 (15)	C10—C11	1.4187 (16)
O2—C18	1.4288 (17)	C10—C15	1.4212 (16)
C1—C2	1.3851 (16)	C11—C12	1.3706 (18)
C1—C6	1.4324 (13)	C11—H11	0.9500
C1—C7	1.5154 (15)	C12—C13	1.408 (2)
C2—C3	1.4106 (18)	C12—H12	0.9500
C3—C4	1.358 (2)	C13—C14	1.366 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.4131 (15)	C14—C15	1.4209 (17)
C4—H4	0.9500	C14—H14	0.9500
C5—C4ⁱ	1.4131 (15)	C15—C16	1.4197 (17)
C5—C6	1.428 (2)	C16—C17	1.3653 (17)
C6—C1ⁱ	1.4324 (13)	C16—H16	0.9500
C7—C8	1.4856 (15)	C17—H17	0.9500
C8—C9	1.3762 (16)	C18—H18A	0.9800
C8—C17	1.4184 (15)	C18—H18B	0.9800
C9—C10	1.4144 (16)	C18—H18C	0.9800

C2—O2—C18	117.62 (11)	C9—C10—C15	118.88 (10)
C2—C1—C6	120.06 (11)	C11—C10—C15	119.09 (11)
C2—C1—C7	117.16 (10)	C12—C11—C10	120.61 (12)
C6—C1—C7	122.22 (10)	C12—C11—H11	119.7
O2—C2—C1	115.90 (11)	C10—C11—H11	119.7
O2—C2—C3	122.35 (11)	C11—C12—C13	120.30 (12)
C1—C2—C3	121.65 (11)	C11—C12—H12	119.8
C4—C3—C2	118.83 (11)	C13—C12—H12	119.9
C4—C3—H3	120.6	C14—C13—C12	120.53 (12)
C2—C3—H3	120.6	C14—C13—H13	119.7
C3—C4—C5	122.14 (12)	C12—C13—H13	119.7
C3—C4—H4	118.9	C13—C14—C15	120.76 (12)
C5—C4—H4	118.9	C13—C14—H14	119.6
C4—C5—C4ⁱ	120.74 (16)	C15—C14—H14	119.6
C4—C5—C6	119.63 (8)	C16—C15—C14	122.22 (11)
C4ⁱ—C5—C6	119.63 (8)	C16—C15—C10	119.08 (10)
C5—C6—C1ⁱ	117.65 (7)	C14—C15—C10	118.70 (11)
C5—C6—C1	117.65 (7)	C17—C16—C15	120.65 (11)
C1ⁱ—C6—C1	124.70 (14)	C17—C16—H16	119.7
O1—C7—C8	121.64 (10)	C15—C16—H16	119.7
O1—C7—C1	118.01 (10)	C16—C17—C8	120.66 (11)
C8—C7—C1	120.33 (9)	C16—C17—H17	119.7
C9—C8—C17	119.60 (10)	C8—C17—H17	119.7
C9—C8—C7	118.51 (10)	O2—C18—H18A	109.5
C17—C8—C7	121.79 (10)	O2—C18—H18B	109.5
C8—C9—C10	121.10 (10)	H18A—C18—H18B	109.5
C8—C9—H9	119.5	O2—C18—H18C	109.5
C10—C9—H9	119.5	H18A—C18—H18C	109.5
C9—C10—C11	122.03 (11)	H18B—C18—H18C	109.5

C18—O2—C2—C1	−162.39 (12)	C1—C7—C8—C9	175.44 (10)
C18—O2—C2—C3	21.28 (19)	O1—C7—C8—C17	−179.51 (11)
C6—C1—C2—O2	−177.66 (9)	C1—C7—C8—C17	−0.90 (16)
C7—C1—C2—O2	−6.05 (15)	C17—C8—C9—C10	1.16 (17)
C6—C1—C2—C3	−1.30 (17)	C7—C8—C9—C10	−175.26 (10)
C7—C1—C2—C3	170.30 (11)	C8—C9—C10—C11	179.74 (11)
O2—C2—C3—C4	175.46 (12)	C8—C9—C10—C15	0.17 (17)
C1—C2—C3—C4	−0.7 (2)	C9—C10—C11—C12	−178.16 (12)
C2—C3—C4—C5	1.68 (19)	C15—C10—C11—C12	1.41 (19)
C3—C4—C5—C4ⁱ	179.28 (14)	C10—C11—C12—C13	−0.7 (2)
C3—C4—C5—C6	−0.72 (14)	C11—C12—C13—C14	−0.3 (2)
C4—C5—C6—C1ⁱ	178.78 (8)	C12—C13—C14—C15	0.7 (2)
C4ⁱ—C5—C6—C1ⁱ	−1.22 (8)	C13—C14—C15—C16	−179.74 (12)
C4—C5—C6—C1	−1.22 (8)	C13—C14—C15—C10	0.01 (18)
C4ⁱ—C5—C6—C1	178.78 (8)	C9—C10—C15—C16	−1.71 (17)
C2—C1—C6—C5	2.20 (11)	C11—C10—C15—C16	178.71 (11)
C7—C1—C6—C5	−168.97 (7)	C9—C10—C15—C14	178.54 (10)
C2—C1—C6—C1ⁱ	−177.80 (11)	C11—C10—C15—C14	−1.04 (17)
C7—C1—C6—C1ⁱ	11.03 (7)	C14—C15—C16—C17	−178.29 (11)
C2—C1—C7—O1	−104.62 (13)	C10—C15—C16—C17	1.97 (17)
C6—C1—C7—O1	66.79 (13)	C15—C16—C17—C8	−0.65 (18)
C2—C1—C7—C8	76.72 (13)	C9—C8—C17—C16	−0.93 (17)
C6—C1—C7—C8	−111.87 (11)	C7—C8—C17—C16	175.37 (10)
O1—C7—C8—C9	−3.17 (16)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3ⁱⁱ—H3ⁱⁱ···O1	0.95	2.59	3.3795 (17)	141
C16ⁱⁱⁱ—H16ⁱⁱⁱ···O1	0.95	2.49	3.4382 (14)	175

Symmetry codes: (ii) −x+3/2, y−1/2, −z+1/2; (iii) x, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₃₄H₂₄O₄
M_r	496.53
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	193
a, b, c (Å)	12.8325 (5), 12.2459 (4), 15.8798 (6)
β (°)	97.618 (1)
V (Å³)	2473.41 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.958, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	19645, 2832, 2370
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.115, 1.11
No. of reflections	2832
No. of parameters	175
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.18

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3ⁱ—H3ⁱ···O1	0.95	2.59	3.3795 (17)	141
C16ⁱⁱ—H16ⁱⁱ···O1	0.95	2.49	3.4382 (14)	175

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x, −y, z−1/2.

Acknowledgements

The authors express their gratitude to Master Atsushi Nagasawa and Mr Kotaro Kataoka, 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 & Technology, for technical advice.

References

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