3-(5,6,7,8-Tetra­hydro-2-naphth­yl)iso­benzofuran-1(3H)-one

Kitamura, C.; Kawase, T.

doi:10.1107/S1600536808024598

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1696

doi:10.1107/S1600536808024598

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3-(5,6,7,8-Tetrahydro-2-naphthyl)isobenzofuran-1(3H)-one

Chitoshi Kitamura ^a ^* and Takeshi Kawase ^a

^aDepartment of Materials Science and Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280, Japan
^*Correspondence e-mail: kitamura@eng.u-hyogo.ac.jp

(Received 26 July 2008; accepted 31 July 2008; online 6 August 2008)

The title compound, C₁₈H₁₆O₂, was prepared by reduction of 2-(5,6,7,8-tetrahydro-2-naphthoyl)benzoic acid with zinc dust. The benzene ring in the tetrahydronaphthyl substituent is nearly perpendicular to the plane of the isobenzofuran-1(3H)-one ring [87.15 (4)°]. The cyclohexane unit has a half-chair conformation in which two methylene groups in the tetramethylene bridge are disordered over two positions; the site-occupancy factors are 0.838 (4) and 0.162 (4). The crystal structure exhibits alternating isobenzofuran-1(3H)-one and tetrahydronaphthalene layers.

Related literature

For related molecular structures, including a 3-phenyl isobenzofuran-1(3H)-one system, see: Chan & Scheidt (2006 ); Kalyani & Vijayan (1969 ); Vijayan et al. (2006 ). For related literature, see: Konosonoks et al. (2005 ); Schroeter (1921 ).

Experimental

Crystal data

C₁₈H₁₆O₂
M_r = 264.31
Monoclinic, P 2₁ /c
a = 11.2950 (11) Å
b = 15.8251 (10) Å
c = 7.8092 (10) Å
β = 109.0970 (10)°
V = 1319.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 223 K
0.5 × 0.5 × 0.03 mm

Data collection

Rigaku/MSC Mercury CCD area-detector diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.980, T_max = 0.995
5765 measured reflections
2955 independent reflections
2502 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.108
S = 1.1
2955 reflections
200 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2001 ); cell refinement: CrystalClear; data reduction: CrystalClear and WinGX (Farrugia, 1999 ); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024598/pk2111sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808024598/pk2111Isup2.hkl

checkCIF report

Comment top

A number of 3-phenylisobenzofuran-1(3H)-one derivatives have been prepared from the corresponding 2-benzoylbenzoic acid by reduction using zinc dust. Several crystal structures including 3-phenylisobenzofuran-1(3H)-one were reported (Chan & Scheidt, 2006; Kalyani & Vijayan, 1969; Konosonoks et al., 2005; Vijayan et al., 2006). The title compound, which was first prepared by Schroeter (1921), can be regarded as a derivative of 3-phenylisobenzofuran-1(3H)-one by annelation of cyclohexane to the substituent phenyl ring. In order to ascertain the effect of the annelation of cyclohexane into the structure, X-ray analysis was performed.

The molecular structure is shown in Fig. 1. The isobenzofuran-1(3H)-one moiety is essentially planar. The benzene ring within the tetrahydronaphthyl substituent is nearly perpendicular to the plane of the isobenzofuran-1(3H)-one ring (87.13 (3)°). The dihedral angle O1—C2—C10—C9 between the isobenzofuran-1(3H)-one ring and the benzene ring is 58.55 (12)°, and is smaller than that (64.49°) of the corresponding 3-phenylisobenzofuran-1(3H)-one (Chan & Scheidt, 2006). The annelated cyclohexane ring has a half-chair configuration. The ethylene unit in the tetramethylene-bridge is disordered over two sites (C14—C15A—C16A—C17 and C14—C15B—C16B—C17) with refined occupancies of 0.838 (4) and 0.162 (4).

As shown in Fig. 2, the crystal structure is characterized by two alternating layers, which consist of the isobenzofuran-1(3H)-one layer lying on the bc planes and the tetrahydro naphthalene layer, which exists between the bc planes.

Related literature top

For related molecular structures, including a 3-phenyl isobenzofuran-1(3H)-one system, see: Chan & Scheidt (2006); Kalyani & Vijayan (1969); Vijayan et al. (2006). For related literature, see: Konosonoks et al. (2005); Schroeter (1921).

Experimental top

The title compound was prepared according to the modified method described by Schroeter (1921). A mixture of 2-(5,6,7,8-tetrahydronaphtho-2-yl)benzoic acid (2.01 g, 7.16 mmol) and zinc dust (2.00 g, 30.6 mmol) in 25% ammonia solution (30 ml) was refluxed for 4 h. The reaction mixture was cooled and conc. HCl (8 ml) was added. The resulting precipitate was filtered off, and washed with dichloromethane. The organic layer was separated, washed with brine, and dried over Na₂SO₄. After evaporation, column chromatography on silica gel (CH₂Cl₂) gave the compound (1.17 g, 62%) as a white solid. Colourless crystals suitable for X-ray analysis were obtained from a dichloromethane solution.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear (Rigaku/MSC, 2001); data reduction: WinGX (Farrugia, 1999); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids for non-H atoms. The minor occupied site of the disordered methylene-bridge chain is omitted for clarity.
	Fig. 2. The packing diagram of (I), viewed down the c axis. Hydrogen atoms are omitted for clarity.

3-(5,6,7,8-Tetrahydro-2-naphthyl)isobenzofuran-1(3H)-one top

Crystal data top

C₁₈H₁₆O₂	F(000) = 560
M_r = 264.31	D_x = 1.331 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4161 reflections
a = 11.2950 (11) Å	θ = 3.1–27.5°
b = 15.8251 (10) Å	µ = 0.09 mm⁻¹
c = 7.8092 (10) Å	T = 223 K
β = 109.097 (1)°	Platelet, colourless
V = 1319.0 (2) Å³	0.5 × 0.5 × 0.03 mm
Z = 4

Data collection top

Rigaku/MSC Mercury CCD area-detector diffractometer	2955 independent reflections
Radiation source: rotating-anode X-ray tube	2502 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
Detector resolution: 14.7059 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ϕ and ω scans	h = −14→0
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −20→20
T_min = 0.980, T_max = 0.995	l = −9→10
5765 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.1	w = 1/[σ²(F_o²) + (0.1123P)² + 0.367P] where P = (F_o² + 2F_c²)/3
2955 reflections	(Δ/σ)_max = 0.001
200 parameters	Δρ_max = 0.23 e Å⁻³
3 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₈H₁₆O₂	V = 1319.0 (2) Å³
M_r = 264.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2950 (11) Å	µ = 0.09 mm⁻¹
b = 15.8251 (10) Å	T = 223 K
c = 7.8092 (10) Å	0.5 × 0.5 × 0.03 mm
β = 109.097 (1)°

Data collection top

Rigaku/MSC Mercury CCD area-detector diffractometer	2955 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2502 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.995	R_int = 0.015
5765 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	3 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.1	Δρ_max = 0.23 e Å⁻³
2955 reflections	Δρ_min = −0.16 e Å⁻³
200 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	Occ. (<1)
C1	1.02994 (10)	0.24031 (7)	0.24158 (14)	0.0297 (2)
C2	0.88406 (10)	0.15608 (7)	0.31444 (13)	0.0275 (2)
H2	0.8899	0.1481	0.4427	0.033*
C3	0.97929 (9)	0.10068 (7)	0.27234 (12)	0.0253 (2)
C4	0.99036 (10)	0.01332 (7)	0.27188 (13)	0.0298 (2)
H4	0.9325	−0.0218	0.3009	0.036*
C5	1.08967 (11)	−0.02030 (7)	0.22709 (14)	0.0333 (3)
H5	1.0999	−0.0793	0.2274	0.04*
C6	1.17465 (11)	0.03146 (8)	0.18158 (14)	0.0349 (3)
H6	1.241	0.0069	0.1514	0.042*
C7	1.16291 (10)	0.11850 (7)	0.18020 (14)	0.0314 (2)
H7	1.2193	0.1537	0.1481	0.038*
C8	1.06447 (10)	0.15181 (7)	0.22818 (12)	0.0261 (2)
C9	0.71587 (10)	0.15338 (7)	0.00822 (13)	0.0268 (2)
H9	0.7772	0.1683	−0.0437	0.032*
C10	0.75057 (10)	0.14339 (6)	0.19540 (13)	0.0254 (2)
C11	0.65959 (11)	0.12144 (7)	0.27084 (14)	0.0309 (2)
H11	0.6811	0.1149	0.397	0.037*
C12	0.53701 (11)	0.10919 (8)	0.16038 (14)	0.0333 (3)
H12	0.4763	0.0939	0.2131	0.04*
C13	0.50144 (10)	0.11891 (6)	−0.02704 (13)	0.0272 (2)
C14	0.36564 (10)	0.10711 (8)	−0.14102 (15)	0.0368 (3)
H14A	0.3166	0.1534	−0.1148	0.044*
H14B	0.3353	0.0543	−0.1046	0.044*
C15A	0.34138 (19)	0.10439 (13)	−0.3451 (2)	0.0362 (5)	0.838 (4)
H15A	0.3638	0.0486	−0.3796	0.043*	0.838 (4)
H15B	0.2522	0.1141	−0.4099	0.043*	0.838 (4)
C16A	0.41910 (14)	0.17205 (11)	−0.39664 (18)	0.0363 (5)	0.838 (4)
H16A	0.3992	0.2275	−0.3573	0.044*	0.838 (4)
H16B	0.3988	0.1734	−0.5286	0.044*	0.838 (4)
C15B	0.3475 (11)	0.1453 (9)	−0.3284 (11)	0.070 (5)	0.162 (4)
H15C	0.2625	0.1325	−0.4085	0.084*	0.162 (4)
H15D	0.3555	0.2068	−0.3169	0.084*	0.162 (4)
C16B	0.4407 (7)	0.1126 (8)	−0.4145 (10)	0.056 (3)	0.162 (4)
H16C	0.4475	0.0509	−0.4059	0.068*	0.162 (4)
H16D	0.4168	0.1292	−0.5422	0.068*	0.162 (4)
C17	0.55921 (11)	0.15332 (8)	−0.30668 (14)	0.0347 (3)
H17A	0.5809	0.1019	−0.3597	0.042*
H17B	0.6084	0.2	−0.3311	0.042*
C18	0.59290 (10)	0.14175 (6)	−0.10368 (13)	0.0257 (2)
O1	0.92438 (7)	0.24194 (5)	0.29001 (10)	0.0330 (2)
O2	1.07896 (8)	0.30458 (5)	0.21603 (11)	0.0418 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0239 (5)	0.0292 (6)	0.0300 (5)	−0.0028 (4)	0.0004 (4)	−0.0003 (4)
C2	0.0265 (6)	0.0272 (5)	0.0274 (5)	−0.0017 (4)	0.0067 (4)	−0.0023 (4)
C3	0.0231 (5)	0.0276 (5)	0.0218 (4)	0.0000 (4)	0.0026 (4)	0.0002 (3)
C4	0.0323 (6)	0.0273 (5)	0.0273 (5)	−0.0015 (4)	0.0062 (4)	0.0024 (4)
C5	0.0372 (6)	0.0272 (6)	0.0317 (5)	0.0053 (4)	0.0063 (4)	−0.0004 (4)
C6	0.0300 (6)	0.0401 (6)	0.0334 (5)	0.0072 (5)	0.0088 (4)	−0.0026 (4)
C7	0.0249 (5)	0.0389 (6)	0.0293 (5)	−0.0016 (4)	0.0072 (4)	0.0012 (4)
C8	0.0232 (5)	0.0268 (5)	0.0237 (4)	−0.0011 (4)	0.0014 (4)	0.0004 (3)
C9	0.0247 (5)	0.0297 (5)	0.0284 (5)	−0.0011 (4)	0.0120 (4)	−0.0014 (4)
C10	0.0237 (5)	0.0247 (5)	0.0278 (5)	0.0014 (4)	0.0083 (4)	−0.0023 (4)
C11	0.0309 (6)	0.0385 (6)	0.0241 (5)	−0.0007 (4)	0.0103 (4)	0.0015 (4)
C12	0.0281 (6)	0.0440 (7)	0.0315 (5)	−0.0030 (5)	0.0147 (4)	0.0018 (4)
C13	0.0228 (5)	0.0295 (5)	0.0298 (5)	0.0009 (4)	0.0092 (4)	−0.0003 (4)
C14	0.0240 (6)	0.0509 (7)	0.0349 (6)	−0.0017 (5)	0.0089 (4)	−0.0013 (5)
C15A	0.0275 (8)	0.0474 (11)	0.0288 (8)	−0.0073 (8)	0.0024 (6)	−0.0018 (7)
C16A	0.0345 (9)	0.0412 (10)	0.0286 (7)	−0.0015 (7)	0.0040 (6)	0.0061 (6)
C15B	0.020 (5)	0.123 (13)	0.054 (6)	−0.001 (7)	−0.007 (4)	−0.044 (8)
C16B	0.042 (5)	0.098 (10)	0.027 (4)	0.012 (5)	0.008 (3)	−0.008 (4)
C17	0.0348 (6)	0.0437 (7)	0.0258 (5)	−0.0052 (5)	0.0103 (4)	0.0010 (4)
C18	0.0262 (5)	0.0261 (5)	0.0256 (5)	0.0008 (4)	0.0099 (4)	−0.0007 (4)
O1	0.0272 (4)	0.0260 (4)	0.0430 (4)	−0.0011 (3)	0.0077 (3)	−0.0056 (3)
O2	0.0370 (5)	0.0279 (4)	0.0544 (5)	−0.0074 (3)	0.0066 (4)	0.0031 (3)

Geometric parameters (Å, º) top

C1—O2	1.2054 (13)	C12—C13	1.3937 (14)
C1—O1	1.3639 (14)	C12—H12	0.94
C1—C8	1.4668 (15)	C13—C18	1.4002 (14)
C2—O1	1.4651 (13)	C13—C14	1.5122 (15)
C2—C10	1.5037 (14)	C14—C15A	1.527 (2)
C2—C3	1.5050 (14)	C14—C15B	1.534 (9)
C2—H2	0.99	C14—H14A	0.98
C3—C8	1.3844 (14)	C14—H14B	0.98
C3—C4	1.3881 (15)	C15A—C16A	1.520 (2)
C4—C5	1.3858 (15)	C15A—H15A	0.98
C4—H4	0.94	C15A—H15B	0.98
C5—C6	1.3935 (17)	C16A—C17	1.5357 (19)
C5—H5	0.94	C16A—H16A	0.98
C6—C7	1.3834 (16)	C16A—H16B	0.98
C6—H6	0.94	C15B—C16B	1.514 (9)
C7—C8	1.3882 (15)	C15B—H15C	0.98
C7—H7	0.94	C15B—H15D	0.98
C9—C18	1.3901 (15)	C16B—C17	1.476 (7)
C9—C10	1.3930 (14)	C16B—H16C	0.98
C9—H9	0.94	C16B—H16D	0.98
C10—C11	1.3856 (14)	C17—C18	1.5155 (14)
C11—C12	1.3846 (16)	C17—H17A	0.98
C11—H11	0.94	C17—H17B	0.98

O2—C1—O1	121.36 (10)	C13—C14—H14A	108.6
O2—C1—C8	130.29 (11)	C15A—C14—H14A	108.6
O1—C1—C8	108.35 (9)	C15B—C14—H14A	89.8
O1—C2—C10	109.57 (8)	C13—C14—H14B	108.6
O1—C2—C3	103.71 (8)	C15A—C14—H14B	108.6
C10—C2—C3	115.52 (8)	C15B—C14—H14B	131.5
O1—C2—H2	109.3	H14A—C14—H14B	107.6
C10—C2—H2	109.3	C16A—C15A—C14	109.54 (14)
C3—C2—H2	109.3	C16A—C15A—H15A	109.8
C8—C3—C4	120.72 (10)	C14—C15A—H15A	109.8
C8—C3—C2	108.57 (9)	C16A—C15A—H15B	109.8
C4—C3—C2	130.71 (10)	C14—C15A—H15B	109.8
C5—C4—C3	117.65 (10)	H15A—C15A—H15B	108.2
C5—C4—H4	121.2	C15A—C16A—C17	109.93 (13)
C3—C4—H4	121.2	C15A—C16A—H16A	109.7
C4—C5—C6	121.37 (10)	C17—C16A—H16A	109.7
C4—C5—H5	119.3	C15A—C16A—H16B	109.7
C6—C5—H5	119.3	C17—C16A—H16B	109.7
C7—C6—C5	120.99 (10)	H16A—C16A—H16B	108.2
C7—C6—H6	119.5	C16B—C15B—C14	113.2 (8)
C5—C6—H6	119.5	C16B—C15B—H15C	108.9
C6—C7—C8	117.33 (10)	C14—C15B—H15C	108.9
C6—C7—H7	121.3	C16B—C15B—H15D	108.9
C8—C7—H7	121.3	C14—C15B—H15D	108.9
C3—C8—C7	121.91 (10)	H15C—C15B—H15D	107.7
C3—C8—C1	108.52 (9)	C17—C16B—C15B	103.3 (8)
C7—C8—C1	129.57 (10)	C17—C16B—H16C	111.1
C18—C9—C10	121.66 (9)	C15B—C16B—H16C	111.1
C18—C9—H9	119.2	C17—C16B—H16D	111.1
C10—C9—H9	119.2	C15B—C16B—H16D	111.1
C11—C10—C9	118.78 (9)	H16C—C16B—H16D	109.1
C11—C10—C2	120.25 (9)	C16B—C17—C18	114.5 (4)
C9—C10—C2	120.97 (9)	C18—C17—C16A	111.74 (10)
C12—C11—C10	119.99 (9)	C16B—C17—H17A	72.7
C12—C11—H11	120	C18—C17—H17A	109.3
C10—C11—H11	120	C16A—C17—H17A	109.3
C11—C12—C13	121.65 (10)	C16B—C17—H17B	133.2
C11—C12—H12	119.2	C18—C17—H17B	109.3
C13—C12—H12	119.2	C16A—C17—H17B	109.3
C12—C13—C18	118.55 (9)	H17A—C17—H17B	107.9
C12—C13—C14	119.53 (9)	C9—C18—C13	119.38 (9)
C18—C13—C14	121.90 (9)	C9—C18—C17	119.92 (9)
C13—C14—C15A	114.77 (11)	C13—C18—C17	120.69 (9)
C13—C14—C15B	107.8 (5)	C1—O1—C2	110.84 (8)

O1—C2—C3—C8	−0.12 (10)	C11—C12—C13—C14	−178.35 (11)
C10—C2—C3—C8	119.79 (9)	C12—C13—C14—C15A	−170.05 (12)
O1—C2—C3—C4	−179.84 (9)	C18—C13—C14—C15A	11.73 (17)
C10—C2—C3—C4	−59.94 (14)	C12—C13—C14—C15B	164.3 (5)
C8—C3—C4—C5	0.44 (14)	C18—C13—C14—C15B	−13.9 (5)
C2—C3—C4—C5	−179.87 (10)	C13—C14—C15A—C16A	−42.2 (2)
C3—C4—C5—C6	−0.87 (15)	C15B—C14—C15A—C16A	36.6 (10)
C4—C5—C6—C7	0.23 (16)	C14—C15A—C16A—C17	63.7 (2)
C5—C6—C7—C8	0.84 (15)	C13—C14—C15B—C16B	52.2 (11)
C4—C3—C8—C7	0.66 (14)	C15A—C14—C15B—C16B	−58.4 (9)
C2—C3—C8—C7	−179.10 (9)	C14—C15B—C16B—C17	−72.0 (13)
C4—C3—C8—C1	−179.57 (8)	C15B—C16B—C17—C18	52.0 (9)
C2—C3—C8—C1	0.67 (10)	C15B—C16B—C17—C16A	−42.7 (6)
C6—C7—C8—C3	−1.29 (14)	C15A—C16A—C17—C16B	48.9 (5)
C6—C7—C8—C1	178.99 (10)	C15A—C16A—C17—C18	−53.52 (17)
O2—C1—C8—C3	179.48 (11)	C10—C9—C18—C13	−0.41 (15)
O1—C1—C8—C3	−1.02 (10)	C10—C9—C18—C17	179.96 (10)
O2—C1—C8—C7	−0.77 (18)	C12—C13—C18—C9	0.49 (15)
O1—C1—C8—C7	178.73 (10)	C14—C13—C18—C9	178.72 (10)
C18—C9—C10—C11	−0.10 (15)	C12—C13—C18—C17	−179.89 (10)
C18—C9—C10—C2	179.91 (9)	C14—C13—C18—C17	−1.65 (16)
O1—C2—C10—C11	−121.44 (10)	C16B—C17—C18—C9	160.3 (5)
C3—C2—C10—C11	121.92 (11)	C16A—C17—C18—C9	−157.81 (11)
O1—C2—C10—C9	58.55 (12)	C16B—C17—C18—C13	−19.3 (5)
C3—C2—C10—C9	−58.09 (13)	C16A—C17—C18—C13	22.56 (15)
C9—C10—C11—C12	0.51 (16)	O2—C1—O1—C2	−179.49 (9)
C2—C10—C11—C12	−179.50 (10)	C8—C1—O1—C2	0.95 (10)
C10—C11—C12—C13	−0.44 (17)	C10—C2—O1—C1	−124.41 (9)
C11—C12—C13—C18	−0.07 (17)	C3—C2—O1—C1	−0.53 (10)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆O₂
M_r	264.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	223
a, b, c (Å)	11.2950 (11), 15.8251 (10), 7.8092 (10)
β (°)	109.097 (1)
V (Å³)	1319.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.5 × 0.5 × 0.03

Data collection
Diffractometer	Rigaku/MSC Mercury CCD area-detector diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.980, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	5765, 2955, 2502
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.108, 1.1
No. of reflections	2955
No. of parameters	200
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.16

Computer programs: CrystalClear (Rigaku/MSC, 2001), WinGX (Farrugia, 1999), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Acknowledgements

We thank the Instrument Center of the Institute for Molecular Science for the X-ray structural analysis. This work was supported by a Grant-in-Aid (No. 20550128) for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

References

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