2-(9,9-Diethyl-9H-fluoren-2-yl)-1-benzofuran

Huang, P.-H.; Lin, K.-L.; Wen, Y.-S.

doi:10.1107/S1600536811006957

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o743

doi:10.1107/S1600536811006957

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2-(9,9-Diethyl-9H-fluoren-2-yl)-1-benzofuran

Ping-Hsin Huang,^a ^* Kai-Ling Lin ^b and Yuh-Sheng Wen ^b

^aCardinal Tien College of Healthcare & Management, Taipei, Taiwan 231, and ^bInstitute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan
^*Correspondence e-mail: pshuang@ctcn.edu.tw

(Received 16 October 2010; accepted 23 February 2011; online 26 February 2011)

In the title compound, C₂₅H₂₂O, the dihedral angle between the benzofuran and fluorene ring systems is 9.06 (6)°, and that between the two benzene rings of the fluorene system is 1.78 (12)°. Weak intermolecular C—H⋯π interactions help to stabilize the crystal structure.

Related literature

The title compound is a precursor for the production of hole-transporting and/or emitting materials, see: Shen et al. (2005 ). For a related structure, see: Bak et al. (1961 ).

Experimental

Crystal data

C₂₅H₂₂O
M_r = 338.43
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.5277 (13) Å
b = 12.9969 (19) Å
c = 18.438 (3) Å
V = 1803.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.2 × 0.14 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
8855 measured reflections
2118 independent reflections
1518 reflections with I > 2σ(I)
R_int = 0.103

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.146
S = 1.03
2118 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C23–C28, O29/C21–C23/C28 and C2–C5/C11/C12 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg1ⁱ	0.95	2.99	3.643 (5)	127
C22—H22⋯Cg1ⁱⁱ	0.95	2.70	3.500 (4)	143
C24—H24⋯Cg2ⁱⁱ	0.95	2.85	3.569 (5)	133
C27—H27⋯Cg2ⁱⁱⁱ	0.95	2.75	3.558 (5)	143
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006957/rn2074sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006957/rn2074Isup2.hkl

checkCIF report

Comment top

The title compound, (I), has been shown to be an precursor for the production of hole transporting and/or emitting materials (Shen et al., 2005). A one pot synthesis of a benzofuran substituted in the 2-position has been achieved by Pd(0) complex catalyzed Sonogashira coupling reaction of 2-iodophenol with terminal alkynes, followed by cyclization of the internal alkynes formed, in high yield (see scheme 1). The molecular structure is shown in Fig. 1. The dihedral angle between the benzofuran and fluorene rings is 9.06 (6)°, and that between the two benzene rings at fluorene is 1.78 (12)°. Weak intermolecular C—H···π interactions help to stabilize the crystal structure.

Related literature top

The title compound is a precursor for the production of hole-transporting and/or emitting materials, see: Shen et al. (2005). For a related structure, see: Bak et al. (1961).

Experimental top

The compound was synthesized by the following procedure. A two-necked round-bottomed flask was charged with PdCl₂(PPh₃)₂ (100 mg), 9,9-diethyl-2-ethynyl-9H-fluorene (1.35 g, 5.46 mmol), CuI (30 mg), 2-iodophenol (1.00 g, 4.55 mmol), triethylamine (1.3 ml), and DMF (10 ml), and the reaction mixture stirred under nitrogen and heated at 333 K for 24 h. After cooling, the mixture was diluted with diethyl ether and the organic phase was washed with water and brine. After drying over anhydrous MgSO₄ and removing the volatiles, the residue was purified by column chromatography using CH₂Cl₂/n-hexane as eluent, followed by recrystallization from CH₂Cl₂ and hexane to yield 0.9 g (59%) of (I) as a white solid. Crystals suitable for X-ray diffraction were grown from a CH₂Cl₂ solution layered with hexane at room temperature. ¹H NMR (CDCl₃): 7.84 (d, 2 H, J = 7.97 Hz), 7.73 (dd, 2 H, J = 7.77 Hz), 7.55 (dd, 2 H, J = 7.64 Hz), 7.35–7.31 (m, 3 H), 7.24 (tt, 2 H, J = 8.31 Hz), 7.06 (s, 1 H), 2.09 (q, 4 H, J = 7.07 Hz), 0.34 (t, 6 H, J = 6.72 Hz). FAB MS (m/e): 338.1 (M⁺) Anal. Calcd for C₂₅H₂₂O: C, 88.72; H, 6.55. Found: C, 88.92; H, 6.51.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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. A molecular structure of (I) with 30% probability displacement ellipsoids, showing the atom-numbering scheme employed. H atoms are shown as small spheres of the arbitrary radii.

2-(9,9-Diethyl-9H-fluoren-2-yl)-1-benzofuran top

Crystal data top

C₂₅H₂₂O	F(000) = 720
M_r = 338.43	D_x = 1.246 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 525 reflections
a = 7.5277 (13) Å	θ = 2.7–20.4°
b = 12.9969 (19) Å	µ = 0.07 mm⁻¹
c = 18.438 (3) Å	T = 100 K
V = 1803.9 (5) Å³	Prism, colourless
Z = 4	0.2 × 0.14 × 0.08 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1518 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.103
Graphite monochromator	θ_max = 26.4°, θ_min = 1.9°
ω and ϕ scans	h = −8→9
8855 measured reflections	k = −16→16
2118 independent reflections	l = −17→23

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)] = 0.058	H-atom parameters constrained
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2118 reflections	Δρ_max = 0.23 e Å⁻³
236 parameters	Δρ_min = −0.26 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: 0.007 (2)

Crystal data top

C₂₅H₂₂O	V = 1803.9 (5) Å³
M_r = 338.43	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.5277 (13) Å	µ = 0.07 mm⁻¹
b = 12.9969 (19) Å	T = 100 K
c = 18.438 (3) Å	0.2 × 0.14 × 0.08 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1518 reflections with I > 2σ(I)
8855 measured reflections	R_int = 0.103
2118 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.03	Δρ_max = 0.23 e Å⁻³
2118 reflections	Δρ_min = −0.26 e Å⁻³
236 parameters

Special details top

Experimental. ¹H NMR (CDCl₃): 7.77 (d, J = 8.2, 4H), 7.64 (d, J = 8.2, 4H). FAB MS (m/e): 462 (M⁺). Analysis calculated for C₁₈H₈F₆N₂O₄S: C 46.76, H 1.74, N 6.06%; found: C 46.80, H 1.88, N 5.79%.

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
O29	0.8727 (4)	0.12706 (16)	0.89298 (15)	0.0233 (6)
C1	0.6113 (5)	0.4536 (2)	0.6667 (2)	0.0210 (9)
C2	0.5957 (6)	0.4834 (3)	0.5267 (2)	0.0241 (9)
H2	0.5355	0.5473	0.5313	0.029*
C3	0.6407 (6)	0.4451 (3)	0.4588 (2)	0.0274 (10)
H3	0.6092	0.4828	0.4166	0.033*
C4	0.7307 (6)	0.3529 (2)	0.4517 (2)	0.0248 (9)
H4	0.7610	0.3284	0.4048	0.030*
C5	0.7768 (6)	0.2960 (2)	0.5121 (2)	0.0250 (9)
H5	0.8382	0.2325	0.5070	0.030*
C6	0.8406 (5)	0.2003 (2)	0.6748 (2)	0.0234 (9)
H6	0.8885	0.1541	0.6400	0.028*
C7	0.8484 (5)	0.1773 (3)	0.7477 (2)	0.0246 (9)
H7	0.9038	0.1152	0.7628	0.030*
C8	0.7765 (5)	0.2434 (2)	0.7995 (2)	0.0203 (8)
C9	0.6972 (5)	0.3362 (2)	0.7766 (2)	0.0221 (9)
H9	0.6485	0.3823	0.8113	0.027*
C10	0.6904 (5)	0.3599 (2)	0.7040 (2)	0.0204 (9)
C11	0.6400 (5)	0.4271 (2)	0.5872 (2)	0.0197 (9)
C12	0.7322 (5)	0.3329 (2)	0.5805 (2)	0.0210 (8)
C13	0.7618 (5)	0.2920 (2)	0.6527 (2)	0.0211 (8)
C21	0.7791 (5)	0.2166 (2)	0.8762 (2)	0.0218 (9)
C22	0.7057 (6)	0.2573 (2)	0.9356 (2)	0.0236 (9)
H22	0.6381	0.3189	0.9376	0.028*
C23	0.7468 (6)	0.1913 (2)	0.9960 (2)	0.0238 (9)
C24	0.7066 (6)	0.1876 (3)	1.0693 (2)	0.0293 (9)
H24	0.6388	0.2407	1.0914	0.035*
C25	0.7675 (6)	0.1048 (3)	1.1097 (2)	0.0311 (10)
H25	0.7404	0.1012	1.1600	0.037*
C26	0.8683 (6)	0.0264 (3)	1.0779 (2)	0.0285 (10)
H26	0.9081	−0.0295	1.1069	0.034*
C27	0.9113 (6)	0.0287 (3)	1.0048 (2)	0.0251 (9)
H27	0.9802	−0.0238	0.9826	0.030*
C28	0.8480 (5)	0.1119 (2)	0.9661 (2)	0.0203 (9)
C31	0.7154 (6)	0.5539 (2)	0.6825 (2)	0.0283 (10)
H31A	0.8425	0.5409	0.6722	0.034*
H31B	0.6745	0.6072	0.6479	0.034*
C32	0.7009 (6)	0.5975 (3)	0.7583 (2)	0.0326 (10)
H32A	0.7727	0.6602	0.7618	0.049*
H32B	0.7441	0.5467	0.7933	0.049*
H32C	0.5764	0.6139	0.7688	0.049*
C33	0.4142 (5)	0.4697 (3)	0.6858 (2)	0.0221 (9)
H33A	0.4039	0.4798	0.7388	0.027*
H33B	0.3724	0.5336	0.6620	0.027*
C34	0.2925 (6)	0.3820 (2)	0.6635 (3)	0.0313 (10)
H34A	0.1703	0.3980	0.6780	0.047*
H34B	0.3309	0.3185	0.6875	0.047*
H34C	0.2978	0.3730	0.6108	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O29	0.0224 (15)	0.0231 (12)	0.0244 (16)	0.0027 (12)	−0.0021 (14)	0.0000 (11)
C1	0.021 (2)	0.0181 (16)	0.024 (2)	0.0023 (16)	0.0017 (19)	−0.0008 (16)
C2	0.026 (2)	0.0220 (17)	0.024 (2)	0.0022 (16)	0.000 (2)	0.0014 (16)
C3	0.032 (3)	0.0265 (18)	0.024 (2)	−0.0026 (18)	−0.001 (2)	0.0017 (16)
C4	0.027 (2)	0.0283 (17)	0.019 (2)	−0.0023 (18)	0.001 (2)	−0.0051 (15)
C5	0.026 (2)	0.0229 (16)	0.026 (2)	0.0002 (17)	0.000 (2)	−0.0015 (16)
C6	0.022 (2)	0.0225 (16)	0.025 (2)	0.0038 (16)	0.0009 (19)	−0.0049 (16)
C7	0.027 (2)	0.0220 (17)	0.025 (2)	0.0029 (16)	−0.0023 (19)	−0.0009 (16)
C8	0.019 (2)	0.0231 (16)	0.0194 (19)	−0.0041 (17)	0.0026 (18)	−0.0015 (15)
C9	0.025 (2)	0.0198 (16)	0.021 (2)	−0.0004 (16)	0.0024 (18)	−0.0031 (15)
C10	0.018 (2)	0.0212 (16)	0.022 (2)	0.0003 (16)	−0.0005 (18)	−0.0003 (15)
C11	0.017 (2)	0.0229 (16)	0.019 (2)	−0.0007 (15)	0.0025 (18)	−0.0027 (15)
C12	0.021 (2)	0.0201 (16)	0.022 (2)	−0.0016 (16)	0.0018 (19)	−0.0024 (15)
C13	0.021 (2)	0.0202 (16)	0.022 (2)	−0.0023 (16)	−0.0017 (19)	−0.0011 (15)
C21	0.017 (2)	0.0174 (16)	0.031 (2)	0.0041 (16)	−0.0059 (19)	0.0002 (15)
C22	0.022 (2)	0.0228 (16)	0.026 (2)	0.0021 (17)	0.0021 (19)	0.0003 (16)
C23	0.021 (2)	0.0260 (17)	0.025 (2)	0.0016 (17)	−0.0014 (19)	0.0023 (15)
C24	0.024 (2)	0.0362 (19)	0.027 (2)	−0.0018 (19)	0.004 (2)	−0.0003 (18)
C25	0.027 (2)	0.039 (2)	0.028 (2)	−0.005 (2)	0.000 (2)	0.0063 (18)
C26	0.025 (2)	0.0282 (18)	0.032 (3)	−0.0032 (18)	−0.009 (2)	0.0078 (18)
C27	0.025 (2)	0.0238 (17)	0.027 (2)	−0.0008 (17)	−0.0040 (19)	−0.0010 (17)
C28	0.022 (2)	0.0253 (17)	0.0139 (19)	−0.0060 (17)	−0.0019 (17)	0.0008 (15)
C31	0.033 (3)	0.0232 (17)	0.029 (2)	−0.0009 (18)	0.003 (2)	−0.0008 (16)
C32	0.034 (3)	0.0305 (19)	0.033 (3)	−0.0078 (19)	−0.002 (2)	−0.0069 (17)
C33	0.025 (2)	0.0215 (17)	0.020 (2)	0.0028 (17)	0.0031 (18)	0.0003 (15)
C34	0.027 (2)	0.0326 (19)	0.034 (2)	−0.0024 (19)	−0.001 (2)	0.0010 (18)

Geometric parameters (Å, º) top

O29—C28	1.374 (5)	C12—C13	1.452 (5)
O29—C21	1.395 (4)	C21—C22	1.336 (5)
C1—C10	1.520 (5)	C22—C23	1.438 (5)
C1—C11	1.521 (5)	C22—H22	0.9500
C1—C33	1.539 (5)	C23—C24	1.386 (6)
C1—C31	1.548 (5)	C23—C28	1.397 (5)
C2—C11	1.375 (5)	C24—C25	1.388 (5)
C2—C3	1.389 (5)	C24—H24	0.9500
C2—H2	0.9500	C25—C26	1.400 (5)
C3—C4	1.382 (5)	C25—H25	0.9500
C3—H3	0.9500	C26—C27	1.386 (6)
C4—C5	1.381 (5)	C26—H26	0.9500
C4—H4	0.9500	C27—C28	1.381 (5)
C5—C12	1.391 (5)	C27—H27	0.9500
C5—H5	0.9500	C31—C32	1.512 (6)
C6—C7	1.377 (6)	C31—H31A	0.9900
C6—C13	1.391 (5)	C31—H31B	0.9900
C6—H6	0.9500	C32—H32A	0.9800
C7—C8	1.396 (5)	C32—H32B	0.9800
C7—H7	0.9500	C32—H32C	0.9800
C8—C9	1.410 (5)	C33—C34	1.519 (5)
C8—C21	1.456 (5)	C33—H33A	0.9900
C9—C10	1.374 (5)	C33—H33B	0.9900
C9—H9	0.9500	C34—H34A	0.9800
C10—C13	1.401 (5)	C34—H34B	0.9800
C11—C12	1.412 (5)	C34—H34C	0.9800

C28—O29—C21	105.6 (3)	C21—C22—C23	108.0 (3)
C10—C1—C11	101.5 (3)	C21—C22—H22	126.0
C10—C1—C33	112.6 (3)	C23—C22—H22	126.0
C11—C1—C33	112.8 (3)	C24—C23—C28	118.6 (3)
C10—C1—C31	113.0 (3)	C24—C23—C22	136.8 (4)
C11—C1—C31	107.4 (3)	C28—C23—C22	104.6 (3)
C33—C1—C31	109.3 (3)	C23—C24—C25	118.6 (4)
C11—C2—C3	118.7 (3)	C23—C24—H24	120.7
C11—C2—H2	120.6	C25—C24—H24	120.7
C3—C2—H2	120.6	C24—C25—C26	121.2 (4)
C4—C3—C2	121.0 (4)	C24—C25—H25	119.4
C4—C3—H3	119.5	C26—C25—H25	119.4
C2—C3—H3	119.5	C27—C26—C25	121.3 (4)
C5—C4—C3	120.7 (4)	C27—C26—H26	119.4
C5—C4—H4	119.6	C25—C26—H26	119.4
C3—C4—H4	119.6	C28—C27—C26	116.0 (4)
C4—C5—C12	119.0 (3)	C28—C27—H27	122.0
C4—C5—H5	120.5	C26—C27—H27	122.0
C12—C5—H5	120.5	O29—C28—C27	124.9 (3)
C7—C6—C13	119.3 (3)	O29—C28—C23	110.8 (3)
C7—C6—H6	120.3	C27—C28—C23	124.3 (4)
C13—C6—H6	120.3	C32—C31—C1	116.9 (3)
C6—C7—C8	121.2 (3)	C32—C31—H31A	108.1
C6—C7—H7	119.4	C1—C31—H31A	108.1
C8—C7—H7	119.4	C32—C31—H31B	108.1
C7—C8—C9	119.0 (3)	C1—C31—H31B	108.1
C7—C8—C21	120.8 (3)	H31A—C31—H31B	107.3
C9—C8—C21	120.1 (3)	C31—C32—H32A	109.5
C10—C9—C8	120.0 (3)	C31—C32—H32B	109.5
C10—C9—H9	120.0	H32A—C32—H32B	109.5
C8—C9—H9	120.0	C31—C32—H32C	109.5
C9—C10—C13	120.1 (3)	H32A—C32—H32C	109.5
C9—C10—C1	129.4 (3)	H32B—C32—H32C	109.5
C13—C10—C1	110.5 (3)	C34—C33—C1	114.7 (3)
C2—C11—C12	120.6 (4)	C34—C33—H33A	108.6
C2—C11—C1	128.8 (3)	C1—C33—H33A	108.6
C12—C11—C1	110.5 (3)	C34—C33—H33B	108.6
C5—C12—C11	119.8 (3)	C1—C33—H33B	108.6
C5—C12—C13	131.9 (3)	H33A—C33—H33B	107.6
C11—C12—C13	108.3 (3)	C33—C34—H34A	109.5
C6—C13—C10	120.4 (4)	C33—C34—H34B	109.5
C6—C13—C12	130.4 (3)	H34A—C34—H34B	109.5
C10—C13—C12	109.2 (3)	C33—C34—H34C	109.5
C22—C21—O29	110.9 (3)	H34A—C34—H34C	109.5
C22—C21—C8	134.1 (3)	H34B—C34—H34C	109.5
O29—C21—C8	115.0 (3)

C11—C2—C3—C4	−0.9 (6)	C1—C10—C13—C12	−1.4 (4)
C2—C3—C4—C5	0.5 (6)	C5—C12—C13—C6	−2.2 (7)
C3—C4—C5—C12	−0.2 (6)	C11—C12—C13—C6	177.5 (4)
C13—C6—C7—C8	0.9 (6)	C5—C12—C13—C10	179.8 (4)
C6—C7—C8—C9	−1.0 (6)	C11—C12—C13—C10	−0.5 (4)
C6—C7—C8—C21	177.6 (4)	C28—O29—C21—C22	2.2 (4)
C7—C8—C9—C10	0.5 (6)	C28—O29—C21—C8	−175.7 (3)
C21—C8—C9—C10	−178.1 (4)	C7—C8—C21—C22	−171.3 (4)
C8—C9—C10—C13	0.2 (6)	C9—C8—C21—C22	7.3 (7)
C8—C9—C10—C1	179.4 (4)	C7—C8—C21—O29	6.0 (5)
C11—C1—C10—C9	−176.8 (4)	C9—C8—C21—O29	−175.4 (3)
C33—C1—C10—C9	−55.9 (6)	O29—C21—C22—C23	−1.4 (5)
C31—C1—C10—C9	68.5 (5)	C8—C21—C22—C23	175.9 (4)
C11—C1—C10—C13	2.5 (4)	C21—C22—C23—C24	−177.1 (5)
C33—C1—C10—C13	123.3 (3)	C21—C22—C23—C28	0.1 (4)
C31—C1—C10—C13	−112.2 (4)	C28—C23—C24—C25	−0.5 (6)
C3—C2—C11—C12	1.1 (6)	C22—C23—C24—C25	176.5 (4)
C3—C2—C11—C1	177.8 (4)	C23—C24—C25—C26	0.3 (6)
C10—C1—C11—C2	−179.8 (4)	C24—C25—C26—C27	0.1 (6)
C33—C1—C11—C2	59.6 (5)	C25—C26—C27—C28	−0.4 (6)
C31—C1—C11—C2	−61.0 (5)	C21—O29—C28—C27	176.8 (4)
C10—C1—C11—C12	−2.8 (4)	C21—O29—C28—C23	−2.1 (4)
C33—C1—C11—C12	−123.5 (3)	C26—C27—C28—O29	−178.5 (4)
C31—C1—C11—C12	116.0 (3)	C26—C27—C28—C23	0.3 (6)
C4—C5—C12—C11	0.4 (6)	C24—C23—C28—O29	179.1 (4)
C4—C5—C12—C13	−179.9 (4)	C22—C23—C28—O29	1.2 (4)
C2—C11—C12—C5	−0.8 (6)	C24—C23—C28—C27	0.2 (6)
C1—C11—C12—C5	−178.1 (4)	C22—C23—C28—C27	−177.7 (4)
C2—C11—C12—C13	179.4 (4)	C10—C1—C31—C32	−71.1 (5)
C1—C11—C12—C13	2.1 (4)	C11—C1—C31—C32	177.8 (3)
C7—C6—C13—C10	−0.3 (6)	C33—C1—C31—C32	55.1 (5)
C7—C6—C13—C12	−178.1 (4)	C10—C1—C33—C34	−61.3 (5)
C9—C10—C13—C6	−0.3 (6)	C11—C1—C33—C34	52.8 (4)
C1—C10—C13—C6	−179.6 (3)	C31—C1—C33—C34	172.2 (3)
C9—C10—C13—C12	178.0 (4)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C23–C28, O29/C21–C23/C28 and C2–C5/C11/C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1ⁱ	0.95	2.99	3.643 (5)	127
C22—H22···Cg1ⁱⁱ	0.95	2.70	3.500 (4)	143
C24—H24···Cg2ⁱⁱ	0.95	2.85	3.569 (5)	133
C27—H27···Cg2ⁱⁱⁱ	0.95	2.75	3.558 (5)	143

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

Experimental details

Crystal data
Chemical formula	C₂₅H₂₂O
M_r	338.43
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	7.5277 (13), 12.9969 (19), 18.438 (3)
V (Å³)	1803.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.2 × 0.14 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8855, 2118, 1518
R_int	0.103
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.146, 1.03
No. of reflections	2118
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C23–C28, O29/C21–C23/C28 and C2–C5/C11/C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1ⁱ	0.95	2.99	3.643 (5)	127
C22—H22···Cg1ⁱⁱ	0.95	2.70	3.500 (4)	143
C24—H24···Cg2ⁱⁱ	0.95	2.85	3.569 (5)	133
C27—H27···Cg2ⁱⁱⁱ	0.95	2.75	3.558 (5)	143

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

Acknowledgements

This work was partially supported by the Institute of Chemistry, Academia Sinica, and Cardinal Tien College of Healthcare & Management.

References

Bak, B., Christensen, D., Hansen-Nygaard, L. & Rastrup-Andersen, J. (1961). J. Mol. Spectrosc. 7, 58–63. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, J. Y., Lee, C. Y., Huang, T.-H., Lin, J. T., Tao, Y.-T., Chien, C.-H. & Tsai, C. (2005). J. Mater. Chem. 15, 2455–2463. Web of Science CrossRef CAS Google Scholar

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Volume 67| Part 3| March 2011| Page o743

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