(3,6-Dimeth­oxy­naphthalen-2-yl)(naphthalen-2-yl)methanone

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

doi:10.1107/S1600536812034186

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2653

doi:10.1107/S1600536812034186

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(3,6-Dimethoxynaphthalen-2-yl)(naphthalen-2-yl)methanone

Takehiro Tsumuki,^a Shun Murohashi,^a Atsushi Nagasawa,^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 23 July 2012; accepted 1 August 2012; online 8 August 2012)

In the title compound, C₂₃H₁₈O₃, the dihedral angle between the two naphthalene ring systems is 78.02 (3)°. The bridging carbonyl C—C(=O)—C plane makes a dihedral angle of 70.56 (5)° with the naphthalene ring system in the 2,7-dimethoxynaphthalene moiety and a dihedral angle of 11.53 (5)° with the naphthalene ring system in the naphthoyl group. In the crystal, adjacent molecules are linked via C—H⋯π interactions, forming chains along [010].

Related literature

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

Experimental

Crystal data

C₂₃H₁₈O₃
M_r = 342.37
Monoclinic, P 2₁ /c
a = 13.4683 (9) Å
b = 8.9062 (5) Å
c = 14.7110 (8) Å
β = 105.646 (2)°
V = 1699.23 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 193 K
0.60 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.941, T_max = 0.983
26536 measured reflections
3863 independent reflections
3436 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.109
S = 1.06
3863 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22A⋯Cg4ⁱ	0.98	2.80	3.5470 (12)	133
Symmetry code: (i) x, y-1, z.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; 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/S1600536812034186/su2487sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034186/su2487Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034186/su2487Isup3.cml

checkCIF report

Comment top

In the course of our studies on selective electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proved to be formed regioselectively with the aid of suitable acidic mediator (Okamoto & Yonezawa, 2009; Okamoto et al., 2011). We have reported the structures of 1,8-dibenzoylnaphthalene analogues such as 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008). The benzoyl groups at the 1,8-positions of the naphthalene rings in these compounds are bonded in a nearly perpendicular manner and orient in opposite directions. The 1-monobenzoylnaphthalene analogues, such as (2,7-dimethoxynaphthalen-1-yl)(phenyl)methanone (Kato et al., 2010), were also revealed to have essentially the same non-coplanar structure as observed for 1,8-dibenzoylated naphthalene analogues. The corresponding β-isomers of 3-monobenzoylated naphthalene analogues such as (3,6-dimethoxynaphthalen-2-yl)(phenyl)methanone (Kato, et al., 2011) and (4-fluorophenyl)(3,6-dimethoxy-2-naphthyl)methanone (Watanabe et al., 2010). In the 3-monobenzoylated naphthalene analogues, which are generally regarded to be thermodynamically more stable than the corresponding 1-positioned isomeric molecules, the aroyl groups are connected to the naphthalene rings in a moderately twisted fashion.

Recently, a series of the corresponding naphthoylated naphthalene homologues to the benzoylated naphthalenes have been reported, such as [2,7-dimethoxy-8-(2-naphthoyl)naphthalen-1-yl](naphthalen-2-yl)methanone (Tsumuki et al., 2011) and 1-(2-naphthoyl)-2,7-dimethoxynaphthalene (Tsumuki et al., 2012). As a part of our ongoing studies on the synthesis and structure of these homologous molecules, the crystal structure analysis of the title compound, a 2,7-dimethoxynaphthalene substituted at the 3-position by a 2-naphthoyl group, is reported on herein.

The molecular structure of the title molecule is illustrated in Fig. 1. The interplanar angle between the two naphthalene rings (C1—C10 and C12—C21) is 78.02 (3)°. The dihedral angle between the bridging carbonyl plane (O1—C3—C11—C12) and the naphthalene ring of the 2,7-demethoxynaphthalene moiety (C1—C10) is larger than that between the bridging carbonyl plane (O1—C3—C11—C12) and naphthalene ring of the naphthoyl group (C12—C21) [70.56 (5)° versus. 11.53 (5)°; torsion angle C2—C3—C11—O1 = -110.65 (13)° versus. torsion angle O1—C11—C12—C13 = -167.08 (11)°]

In the crystal, neighbouring molecules are linked by C—H···π interactions along the b axis (Table 1 and Fig. 2).

Related literature top

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

Experimental top

The title compound was prepared by treatment of a mixture of 2,7-dimethoxynaphthalene (188 mg, 1 mmol) and 2-naphthoic acid (189 mg, 1.1 mmol) with phosphorus pentoxide—methanesulfonic acid mixture (P₂O₅—MsOH [1/10 w/w] 2.2 ml). After the reaction mixture had been stirred at 333 K for 6 h, the mixture was poured into ice-cold water and extracted with CHCl₃ (3 × 10 ml). The combined extracts were washed with 2 M aqueous NaOH (3 × 15 ml) followed by washing with brine ( 3 × 15 ml). The organic layer thus obtained was dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give a cake (yield 349 mg, quant.). The crude product was purified by flush silica gel chromatography (eluent: toluene; isolated yield 28%). Colourless platelet single crystals suitable for X-ray diffraction were obtained by crystallization from chloroform. Spectroscopic data for the title compound are given in the archived CIF.

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: 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 the title molecule, with the atom labeling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial view along the a axis of the crystal packing of the title compound, showing the C—H···π interaction as dashed lines (see Table for details).

(3,6-Dimethoxynaphthalen-2-yl)(naphthalen-2-yl)methanone top

Crystal data top

C₂₃H₁₈O₃	F(000) = 720
M_r = 342.37	D_x = 1.338 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 444.0–445.0 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71075 Å
a = 13.4683 (9) Å	Cell parameters from 20190 reflections
b = 8.9062 (5) Å	θ = 3.1–27.4°
c = 14.7110 (8) Å	µ = 0.09 mm⁻¹
β = 105.646 (2)°	T = 193 K
V = 1699.23 (17) Å³	Block, colourless
Z = 4	0.60 × 0.30 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3863 independent reflections
Radiation source: rotating anode	3436 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −17→17
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −11→11
T_min = 0.941, T_max = 0.983	l = −19→18
26536 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) = 0.109	w = 1/[σ²(F_o²) + (0.0609P)² + 0.3821P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3863 reflections	Δρ_max = 0.31 e Å⁻³
238 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: 0.0154 (19)

Crystal data top

C₂₃H₁₈O₃	V = 1699.23 (17) Å³
M_r = 342.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.4683 (9) Å	µ = 0.09 mm⁻¹
b = 8.9062 (5) Å	T = 193 K
c = 14.7110 (8) Å	0.60 × 0.30 × 0.20 mm
β = 105.646 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3863 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	3436 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.983	R_int = 0.017
26536 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.06	Δρ_max = 0.31 e Å⁻³
3863 reflections	Δρ_min = −0.18 e Å⁻³
238 parameters

Special details top

Experimental. Spectroscopic data for the title compound:

¹H NMR δ (300 MHz, CDCl₃): 3.83 (3H, s), 3.96 (3H, s), 7.07 (1H, dd, J = 2.4, 9.0 Hz), 7.14 (1H, d, J = 2.4 Hz), 7.18 (1H, s), 7.51 (1H, dt, J = 1.2, 7.5 Hz), 7.60 (1H, dt, J = 1.2, 7.5 Hz), 7.71 (1H, d, J = 9.0 Hz), 7.84–7.92 (4H, m), 8.02 (1H, dd, J = 1.2, 9.0 Hz), 8.26 (1H,d, J = 1.2 Hz) p.p.m. ¹³C NMR δ (125 MHz, CDCl₃): 195.97, 159.32, 155.89, 137.11, 135.55, 135.46, 132.39, 132.19, 130.03, 130.01, 129.59, 128.35, 128.05, 128.02, 127.73, 126.52, 125.17, 123.17, 117.02, 105.43, 105.04, 55.56, 55.32 p.p.m. IR (KBr, cm^-1): 1666, 1630, 1459, 1226, 1191 HRMS (m/z): [M+H]⁺ calcd. for C₂₃H₁₉O₃, 343.1334, found, 343.1344.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.31909 (7)	0.44270 (11)	0.02517 (6)	0.0449 (2)
O2	0.21312 (6)	0.25562 (9)	0.18816 (5)	0.03164 (19)
O3	0.66735 (6)	0.30077 (10)	0.59573 (6)	0.0396 (2)
C1	0.35816 (8)	0.26610 (11)	0.32895 (7)	0.0256 (2)
H1	0.3284	0.1931	0.3606	0.031*
C2	0.30615 (7)	0.31204 (11)	0.23965 (7)	0.0248 (2)
C3	0.34880 (8)	0.42318 (11)	0.19167 (7)	0.0252 (2)
C4	0.44353 (8)	0.48307 (12)	0.23457 (7)	0.0282 (2)
H4	0.4720	0.5567	0.2022	0.034*
C5	0.50006 (8)	0.43750 (11)	0.32631 (7)	0.0270 (2)
C6	0.59859 (9)	0.49671 (14)	0.37265 (8)	0.0363 (3)
H6	0.6283	0.5713	0.3420	0.044*
C7	0.65131 (9)	0.44839 (15)	0.46046 (9)	0.0390 (3)
H7	0.7175	0.4886	0.4900	0.047*
C8	0.60763 (8)	0.33873 (13)	0.50744 (7)	0.0311 (2)
C9	0.51225 (8)	0.27940 (12)	0.46576 (7)	0.0278 (2)
H9	0.4834	0.2062	0.4981	0.033*
C10	0.45652 (7)	0.32767 (11)	0.37402 (7)	0.0244 (2)
C11	0.28960 (8)	0.47414 (12)	0.09415 (7)	0.0279 (2)
C12	0.19693 (8)	0.56988 (11)	0.08637 (7)	0.0263 (2)
C13	0.17608 (7)	0.62890 (11)	0.16571 (6)	0.0236 (2)
H13	0.2198	0.6049	0.2262	0.028*
C14	0.09043 (7)	0.72487 (11)	0.15864 (7)	0.0233 (2)
C15	0.06908 (8)	0.78952 (11)	0.23953 (7)	0.0260 (2)
H15	0.1131	0.7686	0.3004	0.031*
C16	−0.01430 (8)	0.88170 (12)	0.23057 (7)	0.0300 (2)
H16	−0.0272	0.9255	0.2851	0.036*
C17	−0.08113 (9)	0.91196 (14)	0.14072 (8)	0.0358 (3)
H17	−0.1393	0.9751	0.1352	0.043*
C18	−0.06276 (9)	0.85107 (15)	0.06142 (8)	0.0408 (3)
H18	−0.1086	0.8719	0.0013	0.049*
C19	0.02400 (9)	0.75705 (13)	0.06789 (7)	0.0318 (2)
C20	0.04710 (10)	0.69372 (16)	−0.01265 (8)	0.0444 (3)
H20	0.0031	0.7144	−0.0736	0.053*
C21	0.13096 (10)	0.60409 (15)	−0.00430 (7)	0.0390 (3)
H21	0.1455	0.5642	−0.0592	0.047*
C22	0.17610 (8)	0.12457 (12)	0.22435 (8)	0.0334 (2)
H22A	0.1108	0.0929	0.1808	0.040*
H22B	0.1652	0.1471	0.2861	0.040*
H22C	0.2269	0.0437	0.2310	0.040*
C23	0.62408 (10)	0.19186 (14)	0.64517 (9)	0.0407 (3)
H23A	0.6707	0.1764	0.7083	0.049*
H23B	0.6147	0.0968	0.6103	0.049*
H23C	0.5572	0.2276	0.6508	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0548 (5)	0.0553 (5)	0.0303 (4)	0.0209 (4)	0.0210 (4)	0.0045 (4)
O2	0.0279 (4)	0.0306 (4)	0.0328 (4)	−0.0027 (3)	0.0019 (3)	0.0078 (3)
O3	0.0329 (4)	0.0456 (5)	0.0342 (4)	−0.0046 (4)	−0.0015 (3)	0.0070 (4)
C1	0.0263 (5)	0.0232 (4)	0.0286 (5)	0.0005 (4)	0.0095 (4)	0.0039 (4)
C2	0.0232 (5)	0.0233 (5)	0.0286 (5)	0.0027 (4)	0.0082 (4)	0.0008 (4)
C3	0.0278 (5)	0.0241 (5)	0.0262 (5)	0.0057 (4)	0.0114 (4)	0.0029 (4)
C4	0.0308 (5)	0.0265 (5)	0.0310 (5)	0.0010 (4)	0.0146 (4)	0.0051 (4)
C5	0.0264 (5)	0.0268 (5)	0.0302 (5)	0.0006 (4)	0.0117 (4)	0.0014 (4)
C6	0.0312 (5)	0.0400 (6)	0.0391 (6)	−0.0085 (5)	0.0120 (5)	0.0065 (5)
C7	0.0279 (5)	0.0464 (7)	0.0404 (6)	−0.0097 (5)	0.0051 (5)	0.0026 (5)
C8	0.0284 (5)	0.0337 (5)	0.0297 (5)	0.0013 (4)	0.0054 (4)	0.0017 (4)
C9	0.0282 (5)	0.0264 (5)	0.0289 (5)	0.0010 (4)	0.0082 (4)	0.0033 (4)
C10	0.0246 (5)	0.0226 (4)	0.0273 (5)	0.0029 (4)	0.0093 (4)	0.0007 (4)
C11	0.0337 (5)	0.0268 (5)	0.0256 (5)	0.0034 (4)	0.0121 (4)	0.0025 (4)
C12	0.0311 (5)	0.0266 (5)	0.0222 (5)	0.0033 (4)	0.0086 (4)	0.0031 (4)
C13	0.0263 (5)	0.0241 (5)	0.0199 (4)	−0.0001 (4)	0.0053 (3)	0.0024 (3)
C14	0.0260 (5)	0.0235 (4)	0.0203 (4)	−0.0009 (4)	0.0061 (4)	0.0013 (3)
C15	0.0300 (5)	0.0269 (5)	0.0215 (4)	0.0002 (4)	0.0075 (4)	0.0010 (4)
C16	0.0343 (5)	0.0304 (5)	0.0280 (5)	0.0021 (4)	0.0131 (4)	−0.0007 (4)
C17	0.0318 (5)	0.0402 (6)	0.0354 (6)	0.0113 (5)	0.0091 (4)	0.0022 (5)
C18	0.0384 (6)	0.0526 (7)	0.0273 (5)	0.0175 (5)	0.0019 (4)	0.0023 (5)
C19	0.0339 (6)	0.0377 (6)	0.0221 (5)	0.0085 (4)	0.0045 (4)	0.0017 (4)
C20	0.0511 (7)	0.0594 (8)	0.0182 (5)	0.0231 (6)	0.0018 (5)	0.0016 (5)
C21	0.0497 (7)	0.0483 (7)	0.0191 (5)	0.0172 (6)	0.0092 (5)	0.0007 (4)
C22	0.0270 (5)	0.0302 (5)	0.0404 (6)	−0.0029 (4)	0.0049 (4)	0.0066 (4)
C23	0.0456 (7)	0.0363 (6)	0.0335 (6)	−0.0015 (5)	−0.0009 (5)	0.0082 (5)

Geometric parameters (Å, º) top

O1—C11	1.2179 (13)	C12—C21	1.4221 (14)
O2—C2	1.3726 (12)	C13—C14	1.4168 (14)
O2—C22	1.4274 (13)	C13—H13	0.9500
O3—C8	1.3729 (13)	C14—C15	1.4195 (13)
O3—C23	1.4276 (15)	C14—C19	1.4215 (14)
C1—C2	1.3739 (14)	C15—C16	1.3684 (14)
C1—C10	1.4219 (14)	C15—H15	0.9500
C1—H1	0.9500	C16—C17	1.4101 (15)
C2—C3	1.4235 (14)	C16—H16	0.9500
C3—C4	1.3698 (15)	C17—C18	1.3683 (16)
C3—C11	1.5109 (14)	C17—H17	0.9500
C4—C5	1.4183 (15)	C18—C19	1.4198 (15)
C4—H4	0.9500	C18—H18	0.9500
C5—C10	1.4195 (14)	C19—C20	1.4204 (15)
C5—C6	1.4198 (15)	C20—C21	1.3613 (17)
C6—C7	1.3651 (17)	C20—H20	0.9500
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.4131 (16)	C22—H22A	0.9800
C7—H7	0.9500	C22—H22B	0.9800
C8—C9	1.3713 (15)	C22—H22C	0.9800
C9—C10	1.4223 (14)	C23—H23A	0.9800
C9—H9	0.9500	C23—H23B	0.9800
C11—C12	1.4903 (14)	C23—H23C	0.9800
C12—C13	1.3762 (13)

C2—O2—C22	116.88 (8)	C12—C13—H13	119.5
C8—O3—C23	115.71 (9)	C14—C13—H13	119.5
C2—C1—C10	120.12 (9)	C13—C14—C15	121.89 (9)
C2—C1—H1	119.9	C13—C14—C19	118.97 (9)
C10—C1—H1	119.9	C15—C14—C19	119.15 (9)
O2—C2—C1	124.94 (9)	C16—C15—C14	120.61 (9)
O2—C2—C3	114.29 (9)	C16—C15—H15	119.7
C1—C2—C3	120.75 (9)	C14—C15—H15	119.7
C4—C3—C2	119.51 (9)	C15—C16—C17	120.32 (10)
C4—C3—C11	120.52 (9)	C15—C16—H16	119.8
C2—C3—C11	119.97 (9)	C17—C16—H16	119.8
C3—C4—C5	121.41 (9)	C18—C17—C16	120.46 (10)
C3—C4—H4	119.3	C18—C17—H17	119.8
C5—C4—H4	119.3	C16—C17—H17	119.8
C4—C5—C10	118.71 (9)	C17—C18—C19	120.75 (10)
C4—C5—C6	122.88 (10)	C17—C18—H18	119.6
C10—C5—C6	118.41 (9)	C19—C18—H18	119.6
C7—C6—C5	121.17 (10)	C18—C19—C20	122.66 (10)
C7—C6—H6	119.4	C18—C19—C14	118.69 (10)
C5—C6—H6	119.4	C20—C19—C14	118.65 (10)
C6—C7—C8	120.11 (10)	C21—C20—C19	121.38 (10)
C6—C7—H7	119.9	C21—C20—H20	119.3
C8—C7—H7	119.9	C19—C20—H20	119.3
C9—C8—O3	124.56 (10)	C20—C21—C12	120.23 (10)
C9—C8—C7	120.73 (10)	C20—C21—H21	119.9
O3—C8—C7	114.70 (10)	C12—C21—H21	119.9
C8—C9—C10	119.91 (9)	O2—C22—H22A	109.5
C8—C9—H9	120.0	O2—C22—H22B	109.5
C10—C9—H9	120.0	H22A—C22—H22B	109.5
C5—C10—C1	119.49 (9)	O2—C22—H22C	109.5
C5—C10—C9	119.65 (9)	H22A—C22—H22C	109.5
C1—C10—C9	120.85 (9)	H22B—C22—H22C	109.5
O1—C11—C12	121.47 (9)	O3—C23—H23A	109.5
O1—C11—C3	121.00 (10)	O3—C23—H23B	109.5
C12—C11—C3	117.47 (8)	H23A—C23—H23B	109.5
C13—C12—C21	119.66 (9)	O3—C23—H23C	109.5
C13—C12—C11	120.77 (9)	H23A—C23—H23C	109.5
C21—C12—C11	119.54 (9)	H23B—C23—H23C	109.5
C12—C13—C14	121.10 (9)

C22—O2—C2—C1	−10.08 (15)	C4—C3—C11—O1	69.33 (15)
C22—O2—C2—C3	168.17 (9)	C2—C3—C11—O1	−110.65 (12)
C10—C1—C2—O2	177.09 (9)	C4—C3—C11—C12	−107.91 (11)
C10—C1—C2—C3	−1.05 (15)	C2—C3—C11—C12	72.11 (12)
O2—C2—C3—C4	−177.28 (9)	O1—C11—C12—C13	−167.09 (11)
C1—C2—C3—C4	1.06 (15)	C3—C11—C12—C13	10.14 (15)
O2—C2—C3—C11	2.70 (13)	O1—C11—C12—C21	11.11 (17)
C1—C2—C3—C11	−178.96 (9)	C3—C11—C12—C21	−171.67 (10)
C2—C3—C4—C5	−0.43 (15)	C21—C12—C13—C14	−0.74 (16)
C11—C3—C4—C5	179.59 (9)	C11—C12—C13—C14	177.45 (9)
C3—C4—C5—C10	−0.18 (15)	C12—C13—C14—C15	−178.53 (9)
C3—C4—C5—C6	179.70 (10)	C12—C13—C14—C19	1.56 (15)
C4—C5—C6—C7	−179.03 (11)	C13—C14—C15—C16	−179.92 (9)
C10—C5—C6—C7	0.85 (18)	C19—C14—C15—C16	−0.01 (15)
C5—C6—C7—C8	−0.7 (2)	C14—C15—C16—C17	0.94 (16)
C23—O3—C8—C9	−0.16 (16)	C15—C16—C17—C18	−0.79 (18)
C23—O3—C8—C7	179.06 (11)	C16—C17—C18—C19	−0.3 (2)
C6—C7—C8—C9	0.08 (19)	C17—C18—C19—C20	−178.80 (13)
C6—C7—C8—O3	−179.18 (11)	C17—C18—C19—C14	1.23 (19)
O3—C8—C9—C10	179.53 (10)	C13—C14—C19—C18	178.85 (10)
C7—C8—C9—C10	0.36 (17)	C15—C14—C19—C18	−1.07 (16)
C4—C5—C10—C1	0.18 (14)	C13—C14—C19—C20	−1.11 (16)
C6—C5—C10—C1	−179.70 (10)	C15—C14—C19—C20	178.97 (11)
C4—C5—C10—C9	179.48 (9)	C18—C19—C20—C21	179.91 (14)
C6—C5—C10—C9	−0.40 (15)	C14—C19—C20—C21	−0.1 (2)
C2—C1—C10—C5	0.43 (15)	C19—C20—C21—C12	1.0 (2)
C2—C1—C10—C9	−178.86 (9)	C13—C12—C21—C20	−0.54 (19)
C8—C9—C10—C5	−0.18 (15)	C11—C12—C21—C20	−178.75 (12)
C8—C9—C10—C1	179.10 (9)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22A···Cg4ⁱ	0.98	2.80	3.5470 (12)	133

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈O₃
M_r	342.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	13.4683 (9), 8.9062 (5), 14.7110 (8)
β (°)	105.646 (2)
V (Å³)	1699.23 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.60 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.941, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	26536, 3863, 3436
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.109, 1.06
No. of reflections	3863
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.18

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22A···Cg4ⁱ	0.98	2.80	3.5470 (12)	133

Symmetry code: (i) x, y−1, 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 Iron and Steel Institute of Japan (ISIJ) Research Promotion Grant.

References

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Volume 68| Part 9| September 2012| Page o2653

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