2-Methyl-1,1,3,3-tetra­phenyl­propan-2-ol

Shi, D.-X.; Zhang, L.-J.; Zhang, Q.; Li, J.-R.

doi:10.1107/S1600536808014761

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1115

doi:10.1107/S1600536808014761

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2-Methyl-1,1,3,3-tetraphenylpropan-2-ol

Da-Xin Shi,^a Li-Jun Zhang,^a Qi Zhang ^a and Jia-Rong Li ^a ^*

^aSchool of Chemical Engineering and the Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China
^*Correspondence e-mail: jrli@bit.edu.cn

(Received 14 April 2008; accepted 15 May 2008; online 21 May 2008)

The title compound, C₂₈H₂₆O, was synthesized by condensation of diphenylmethyllithium and ethyl acetate. In one diphenylmethyl group, the two benzene rings are rotated by 65.0 (3)° with respect to each other, while in the other diphenylmethyl group, the dihedral angle between the two benzene rings is 84.1 (3)°.

Related literature

For related literature, see: Bunce & Dowdy (1990 ); Ibis & Deniz (2007 ); Lednicer et al. (1990 ).

Experimental

Crystal data

C₂₈H₂₆O
M_r = 378.49
Monoclinic, P 2₁ /n
a = 8.4313 (4) Å
b = 23.8539 (11) Å
c = 10.3420 (5) Å
β = 96.624 (3)°
V = 2066.09 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 113 (2) K
0.22 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.980, T_max = 0.985
15409 measured reflections
3633 independent reflections
3442 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.116
S = 1.11
3633 reflections
267 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2006 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014761/pk2096sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808014761/pk2096Isup2.hkl

checkCIF report

Comment top

Diphenylmethane derivatives are potentially useful precursors to a variety of medicinal agents (Lednicer et al.,1990). In our approach to the preparation of diphenylacetone by reaction of diphenylmethyllithium with ethyl acetate (Bunce & Dowdy, 1990), the title compound, 2-methyl-1,1,3,3-tetraphenylpropan-2-ol, was formed as a double addition product.

There are two diphenymethyl groups in the title compound. In one of these, the two benzene rings are inclined at an angle of 115.0 (3)°, and in the other the dihedral angle between the two benzene rings is 84.1 (3)° which is somewhat different from the corresponding angles found in 3,4,4-trichloro-1-[4-(diphenylmethyl)-piperazine-1-yl]- 2-nitro-1-(propylsulfanyl)-buta-1,3-diene, viz. 80.6 (1)° (Ibis & Deniz, 2007). The plane (C4/C2/O1) and plane (C1/C2/C3) are rotated 92.4 (3)° with respect to each other.

Related literature top

For related literature, see: Bunce & Dowdy (1990); Ibis & Deniz (2007); Lednicer et al. (1990).

Experimental top

To a stirred solution of ethyl acetate (20 mmol) in dry THF (30 ml) a solution of diphenylmethyllithium (40 mmol) in THF (30 ml) was added dropwise. After stirring at room temperature for 20 min to ensure complete reaction, the mixture was cooled and quenched with HCl (1M, 50 ml). The mixture was transferred to a separatory funnel and extrated with ether (40 ml) 3 times. Then, the ether was washed with saturated aqueous Na₂CO₃, water and dried with sodium sulfate. Evaporation of the solvent and recrystallization from petroleum ether yielded precipitate as fine colorless needles. M.p. 406–408 K; IR (KBr): 3563(O—H), 3026,2938 (C—H) cm^-1; ¹H-NMR(CDCl₃, p.p.m.): 1.30 (3H, s), 1.69 (1H, s), 4.13 (2H, s),7.21–7.45 (20H, m); ¹³C-NMR(CDCl₃, p.p.m.): 25.7, 60.5, 71.4,126.5, 128.2, 130.2, 141.2; The product (100 mg) was dissolved in ethyl acetate (2 ml) and petroleum ether (5 ml) and the solution was kept at room temperature for 5 d yielding colorless single crystals.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2006).

Figures top

	Fig. 1. The molecular structure, drawn with 30% probability ellipsoids
	Fig. 2. The crystal structure, viewed along a axis

2-Methyl-1,1,3,3-tetraphenylpropan-2-ol top

Crystal data top

C₂₈H₂₆O	F(000) = 808
M_r = 378.49	D_x = 1.217 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 4487 reflections
a = 8.4313 (4) Å	θ = 2.2–27.9°
b = 23.8539 (11) Å	µ = 0.07 mm⁻¹
c = 10.3420 (5) Å	T = 113 K
β = 96.624 (3)°	Prism, colorless
V = 2066.09 (17) Å³	0.22 × 0.20 × 0.18 mm
Z = 4

Data collection top

Rigaku Saturn CCD diffractometer	3633 independent reflections
Radiation source: rotating anode	3442 reflections with I > 2σ(I)
Confocal multilayer optics monochromator	R_int = 0.050
Detector resolution: 14.63 pixels mm^-1	θ_max = 25.0°, θ_min = 2.2°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −28→28
T_min = 0.980, T_max = 0.985	l = −12→11
15409 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)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0381P)² + 0.9679P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
3633 reflections	Δρ_max = 0.19 e Å⁻³
267 parameters	Δρ_min = −0.20 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: 0.0182 (16)

Crystal data top

C₂₈H₂₆O	V = 2066.09 (17) Å³
M_r = 378.49	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.4313 (4) Å	µ = 0.07 mm⁻¹
b = 23.8539 (11) Å	T = 113 K
c = 10.3420 (5) Å	0.22 × 0.20 × 0.18 mm
β = 96.624 (3)°

Data collection top

Rigaku Saturn CCD diffractometer	3633 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3442 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.985	R_int = 0.050
15409 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.19 e Å⁻³
3633 reflections	Δρ_min = −0.20 e Å⁻³
267 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	0.31548 (15)	0.05491 (5)	0.07175 (11)	0.0266 (3)
H1	0.261 (3)	0.0232 (9)	0.082 (2)	0.040*
C1	0.47972 (19)	0.12873 (7)	0.18234 (16)	0.0200 (4)
H1A	0.5215	0.1406	0.2726	0.024*
C2	0.3887 (2)	0.07256 (7)	0.19928 (16)	0.0210 (4)
C3	0.2473 (2)	0.08319 (7)	0.28398 (16)	0.0207 (4)
H3	0.1715	0.1080	0.2289	0.025*
C4	0.5084 (2)	0.02774 (7)	0.25298 (18)	0.0257 (4)
H4A	0.4507	−0.0057	0.2766	0.039*
H4B	0.5737	0.0423	0.3302	0.039*
H4C	0.5775	0.0179	0.1865	0.039*
C5	0.3781 (2)	0.17823 (7)	0.12541 (16)	0.0209 (4)
C6	0.3655 (2)	0.22646 (7)	0.20063 (17)	0.0242 (4)
H6	0.4124	0.2268	0.2887	0.029*
C7	0.2853 (2)	0.27396 (8)	0.14873 (19)	0.0312 (5)
H7	0.2785	0.3064	0.2011	0.037*
C8	0.2156 (2)	0.27379 (8)	0.02062 (19)	0.0309 (5)
H8	0.1609	0.3060	−0.0151	0.037*
C9	0.2263 (2)	0.22615 (8)	−0.05520 (18)	0.0283 (4)
H9	0.1781	0.2259	−0.1429	0.034*
C10	0.3073 (2)	0.17876 (7)	−0.00380 (16)	0.0234 (4)
H10	0.3145	0.1466	−0.0569	0.028*
C11	0.6273 (2)	0.12517 (7)	0.10844 (16)	0.0209 (4)
C12	0.6302 (2)	0.09609 (7)	−0.00935 (16)	0.0247 (4)
H12	0.5411	0.0739	−0.0425	0.030*
C13	0.7628 (2)	0.09956 (7)	−0.07790 (17)	0.0258 (4)
H13	0.7640	0.0792	−0.1567	0.031*
C14	0.8932 (2)	0.13250 (7)	−0.03209 (17)	0.0259 (4)
H14	0.9823	0.1352	−0.0802	0.031*
C15	0.8925 (2)	0.16146 (7)	0.08431 (18)	0.0255 (4)
H15	0.9812	0.1841	0.1161	0.031*
C16	0.7610 (2)	0.15716 (7)	0.15446 (17)	0.0236 (4)
H16	0.7624	0.1764	0.2351	0.028*
C17	0.2875 (2)	0.11566 (7)	0.41090 (16)	0.0217 (4)
C18	0.1949 (2)	0.16277 (7)	0.43236 (18)	0.0280 (4)
H18	0.1090	0.1729	0.3690	0.034*
C19	0.2261 (3)	0.19528 (8)	0.54486 (19)	0.0348 (5)
H19	0.1623	0.2273	0.5569	0.042*
C20	0.3501 (3)	0.18077 (8)	0.63886 (19)	0.0350 (5)
H20	0.3735	0.2033	0.7143	0.042*
C21	0.4394 (2)	0.13327 (8)	0.62203 (18)	0.0318 (5)
H21	0.5215	0.1223	0.6879	0.038*
C22	0.4095 (2)	0.10121 (8)	0.50852 (16)	0.0261 (4)
H22	0.4731	0.0691	0.4976	0.031*
C23	0.1510 (2)	0.02965 (7)	0.30277 (16)	0.0210 (4)
C24	0.1924 (2)	−0.00805 (7)	0.40487 (17)	0.0258 (4)
H24	0.2827	−0.0004	0.4661	0.031*
C25	0.1038 (2)	−0.05649 (8)	0.41854 (18)	0.0294 (4)
H25	0.1350	−0.0818	0.4878	0.035*
C26	−0.0301 (2)	−0.06799 (8)	0.33105 (18)	0.0296 (4)
H26	−0.0910	−0.1009	0.3406	0.035*
C27	−0.0739 (2)	−0.03107 (8)	0.22989 (19)	0.0287 (4)
H27	−0.1651	−0.0388	0.1697	0.034*
C28	0.0153 (2)	0.01748 (7)	0.21599 (17)	0.0252 (4)
H28	−0.0165	0.0426	0.1466	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0300 (7)	0.0285 (7)	0.0213 (7)	−0.0063 (6)	0.0031 (5)	−0.0030 (5)
C1	0.0198 (9)	0.0214 (9)	0.0188 (8)	−0.0009 (7)	0.0027 (7)	−0.0011 (7)
C2	0.0238 (9)	0.0214 (9)	0.0177 (8)	0.0001 (7)	0.0021 (7)	−0.0016 (7)
C3	0.0212 (9)	0.0208 (9)	0.0205 (9)	0.0019 (7)	0.0037 (7)	0.0013 (7)
C4	0.0252 (10)	0.0236 (9)	0.0290 (10)	0.0027 (7)	0.0056 (8)	0.0040 (7)
C5	0.0180 (9)	0.0234 (9)	0.0221 (9)	−0.0016 (7)	0.0057 (7)	0.0019 (7)
C6	0.0245 (9)	0.0240 (9)	0.0245 (9)	−0.0012 (7)	0.0041 (7)	−0.0024 (7)
C7	0.0361 (11)	0.0231 (10)	0.0362 (11)	0.0036 (8)	0.0116 (9)	−0.0011 (8)
C8	0.0329 (11)	0.0273 (10)	0.0339 (11)	0.0088 (8)	0.0104 (8)	0.0071 (8)
C9	0.0274 (10)	0.0332 (11)	0.0250 (10)	0.0058 (8)	0.0064 (8)	0.0054 (8)
C10	0.0239 (9)	0.0246 (9)	0.0224 (9)	0.0033 (7)	0.0058 (7)	0.0011 (7)
C11	0.0215 (9)	0.0196 (9)	0.0217 (9)	0.0031 (7)	0.0027 (7)	0.0034 (7)
C12	0.0244 (9)	0.0252 (9)	0.0248 (9)	−0.0015 (7)	0.0037 (7)	−0.0022 (7)
C13	0.0274 (10)	0.0260 (10)	0.0244 (9)	0.0017 (8)	0.0052 (8)	−0.0009 (7)
C14	0.0234 (9)	0.0264 (10)	0.0292 (10)	0.0017 (7)	0.0089 (8)	0.0041 (8)
C15	0.0217 (9)	0.0227 (9)	0.0322 (10)	−0.0014 (7)	0.0032 (8)	−0.0001 (7)
C16	0.0237 (9)	0.0238 (9)	0.0231 (9)	0.0007 (7)	0.0017 (7)	−0.0011 (7)
C17	0.0240 (9)	0.0215 (9)	0.0210 (9)	−0.0042 (7)	0.0081 (7)	0.0002 (7)
C18	0.0326 (11)	0.0239 (10)	0.0294 (10)	−0.0018 (8)	0.0113 (8)	0.0005 (8)
C19	0.0460 (13)	0.0260 (10)	0.0362 (11)	−0.0046 (9)	0.0212 (10)	−0.0065 (8)
C20	0.0457 (12)	0.0347 (11)	0.0272 (10)	−0.0174 (9)	0.0155 (9)	−0.0111 (8)
C21	0.0343 (11)	0.0390 (11)	0.0224 (9)	−0.0122 (9)	0.0044 (8)	−0.0006 (8)
C22	0.0287 (10)	0.0262 (10)	0.0242 (9)	−0.0040 (8)	0.0057 (8)	−0.0011 (7)
C23	0.0224 (9)	0.0196 (9)	0.0219 (9)	0.0017 (7)	0.0060 (7)	−0.0017 (7)
C24	0.0279 (10)	0.0277 (10)	0.0222 (9)	−0.0009 (8)	0.0045 (7)	0.0005 (7)
C25	0.0358 (11)	0.0264 (10)	0.0277 (10)	−0.0007 (8)	0.0105 (8)	0.0035 (8)
C26	0.0295 (10)	0.0269 (10)	0.0347 (11)	−0.0051 (8)	0.0139 (8)	−0.0030 (8)
C27	0.0232 (10)	0.0292 (10)	0.0342 (10)	−0.0040 (8)	0.0052 (8)	−0.0049 (8)
C28	0.0237 (9)	0.0256 (9)	0.0263 (10)	0.0024 (7)	0.0032 (7)	0.0013 (7)

Geometric parameters (Å, º) top

O1—C2	1.453 (2)	C13—C14	1.389 (3)
O1—H1	0.90 (2)	C13—H13	0.9500
C1—C5	1.536 (2)	C14—C15	1.388 (3)
C1—C11	1.536 (2)	C14—H14	0.9500
C1—C2	1.564 (2)	C15—C16	1.397 (2)
C1—H1A	1.0000	C15—H15	0.9500
C2—C4	1.530 (2)	C16—H16	0.9500
C2—C3	1.579 (2)	C17—C22	1.399 (2)
C3—C17	1.528 (2)	C17—C18	1.400 (2)
C3—C23	1.538 (2)	C18—C19	1.398 (3)
C3—H3	1.0000	C18—H18	0.9500
C4—H4A	0.9800	C19—C20	1.387 (3)
C4—H4B	0.9800	C19—H19	0.9500
C4—H4C	0.9800	C20—C21	1.383 (3)
C5—C10	1.399 (2)	C20—H20	0.9500
C5—C6	1.400 (2)	C21—C22	1.399 (3)
C6—C7	1.394 (3)	C21—H21	0.9500
C6—H6	0.9500	C22—H22	0.9500
C7—C8	1.386 (3)	C23—C24	1.400 (2)
C7—H7	0.9500	C23—C28	1.401 (2)
C8—C9	1.390 (3)	C24—C25	1.392 (3)
C8—H8	0.9500	C24—H24	0.9500
C9—C10	1.394 (2)	C25—C26	1.390 (3)
C9—H9	0.9500	C25—H25	0.9500
C10—H10	0.9500	C26—C27	1.385 (3)
C11—C16	1.398 (2)	C26—H26	0.9500
C11—C12	1.405 (2)	C27—C28	1.398 (2)
C12—C13	1.394 (2)	C27—H27	0.9500
C12—H12	0.9500	C28—H28	0.9500

C2—O1—H1	108.2 (13)	C14—C13—C12	120.65 (16)
C5—C1—C11	107.46 (13)	C14—C13—H13	119.7
C5—C1—C2	116.24 (14)	C12—C13—H13	119.7
C11—C1—C2	116.40 (13)	C15—C14—C13	119.67 (16)
C5—C1—H1A	105.2	C15—C14—H14	120.2
C11—C1—H1A	105.2	C13—C14—H14	120.2
C2—C1—H1A	105.2	C14—C15—C16	119.77 (17)
O1—C2—C4	108.69 (13)	C14—C15—H15	120.1
O1—C2—C1	108.02 (13)	C16—C15—H15	120.1
C4—C2—C1	109.12 (14)	C15—C16—C11	121.34 (16)
O1—C2—C3	106.33 (13)	C15—C16—H16	119.3
C4—C2—C3	114.80 (13)	C11—C16—H16	119.3
C1—C2—C3	109.65 (13)	C22—C17—C18	117.40 (16)
C17—C3—C23	112.37 (13)	C22—C17—C3	124.53 (16)
C17—C3—C2	116.80 (14)	C18—C17—C3	118.06 (16)
C23—C3—C2	112.33 (13)	C19—C18—C17	121.51 (18)
C17—C3—H3	104.6	C19—C18—H18	119.2
C23—C3—H3	104.6	C17—C18—H18	119.2
C2—C3—H3	104.6	C20—C19—C18	119.93 (18)
C2—C4—H4A	109.5	C20—C19—H19	120.0
C2—C4—H4B	109.5	C18—C19—H19	120.0
H4A—C4—H4B	109.5	C21—C20—C19	119.59 (18)
C2—C4—H4C	109.5	C21—C20—H20	120.2
H4A—C4—H4C	109.5	C19—C20—H20	120.2
H4B—C4—H4C	109.5	C20—C21—C22	120.35 (19)
C10—C5—C6	118.16 (16)	C20—C21—H21	119.8
C10—C5—C1	122.05 (15)	C22—C21—H21	119.8
C6—C5—C1	119.58 (15)	C17—C22—C21	121.15 (18)
C7—C6—C5	121.22 (17)	C17—C22—H22	119.4
C7—C6—H6	119.4	C21—C22—H22	119.4
C5—C6—H6	119.4	C24—C23—C28	117.65 (16)
C8—C7—C6	119.91 (17)	C24—C23—C3	122.67 (15)
C8—C7—H7	120.0	C28—C23—C3	119.68 (15)
C6—C7—H7	120.0	C25—C24—C23	121.34 (17)
C7—C8—C9	119.59 (17)	C25—C24—H24	119.3
C7—C8—H8	120.2	C23—C24—H24	119.3
C9—C8—H8	120.2	C26—C25—C24	120.16 (17)
C8—C9—C10	120.59 (17)	C26—C25—H25	119.9
C8—C9—H9	119.7	C24—C25—H25	119.9
C10—C9—H9	119.7	C27—C26—C25	119.49 (17)
C9—C10—C5	120.51 (16)	C27—C26—H26	120.3
C9—C10—H10	119.7	C25—C26—H26	120.3
C5—C10—H10	119.7	C26—C27—C28	120.31 (18)
C16—C11—C12	118.10 (16)	C26—C27—H27	119.8
C16—C11—C1	117.90 (15)	C28—C27—H27	119.8
C12—C11—C1	123.70 (15)	C27—C28—C23	121.03 (17)
C13—C12—C11	120.46 (16)	C27—C28—H28	119.5
C13—C12—H12	119.8	C23—C28—H28	119.5
C11—C12—H12	119.8

C5—C1—C2—O1	60.36 (17)	C11—C12—C13—C14	−1.0 (3)
C11—C1—C2—O1	−67.83 (17)	C12—C13—C14—C15	1.1 (3)
C5—C1—C2—C4	178.36 (13)	C13—C14—C15—C16	0.1 (3)
C11—C1—C2—C4	50.16 (19)	C14—C15—C16—C11	−1.5 (3)
C5—C1—C2—C3	−55.11 (18)	C12—C11—C16—C15	1.6 (3)
C11—C1—C2—C3	176.70 (13)	C1—C11—C16—C15	−172.30 (15)
O1—C2—C3—C17	−165.43 (13)	C23—C3—C17—C22	78.1 (2)
C4—C2—C3—C17	74.36 (19)	C2—C3—C17—C22	−53.8 (2)
C1—C2—C3—C17	−48.89 (19)	C23—C3—C17—C18	−101.00 (18)
O1—C2—C3—C23	62.63 (17)	C2—C3—C17—C18	127.07 (16)
C4—C2—C3—C23	−57.59 (19)	C22—C17—C18—C19	2.0 (3)
C1—C2—C3—C23	179.17 (13)	C3—C17—C18—C19	−178.79 (16)
C11—C1—C5—C10	64.1 (2)	C17—C18—C19—C20	−0.6 (3)
C2—C1—C5—C10	−68.3 (2)	C18—C19—C20—C21	−1.7 (3)
C11—C1—C5—C6	−110.57 (17)	C19—C20—C21—C22	2.6 (3)
C2—C1—C5—C6	116.99 (17)	C18—C17—C22—C21	−1.1 (2)
C10—C5—C6—C7	−0.3 (3)	C3—C17—C22—C21	179.75 (16)
C1—C5—C6—C7	174.63 (16)	C20—C21—C22—C17	−1.2 (3)
C5—C6—C7—C8	0.4 (3)	C17—C3—C23—C24	−46.2 (2)
C6—C7—C8—C9	0.0 (3)	C2—C3—C23—C24	87.94 (19)
C7—C8—C9—C10	−0.4 (3)	C17—C3—C23—C28	133.29 (16)
C8—C9—C10—C5	0.5 (3)	C2—C3—C23—C28	−92.59 (18)
C6—C5—C10—C9	−0.2 (2)	C28—C23—C24—C25	1.2 (3)
C1—C5—C10—C9	−174.93 (15)	C3—C23—C24—C25	−179.32 (16)
C5—C1—C11—C16	87.47 (18)	C23—C24—C25—C26	−0.9 (3)
C2—C1—C11—C16	−140.18 (16)	C24—C25—C26—C27	0.4 (3)
C5—C1—C11—C12	−86.06 (19)	C25—C26—C27—C28	−0.2 (3)
C2—C1—C11—C12	46.3 (2)	C26—C27—C28—C23	0.5 (3)
C16—C11—C12—C13	−0.3 (3)	C24—C23—C28—C27	−1.0 (2)
C1—C11—C12—C13	173.18 (16)	C3—C23—C28—C27	179.51 (15)

Experimental details

Crystal data
Chemical formula	C₂₈H₂₆O
M_r	378.49
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	8.4313 (4), 23.8539 (11), 10.3420 (5)
β (°)	96.624 (3)
V (Å³)	2066.09 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku Saturn CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.980, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	15409, 3633, 3442
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.116, 1.11
No. of reflections	3633
No. of parameters	267
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2006).

References

Bunce, R. A. & Dowdy, E. D. (1990). Synth. Commun. 20, 3007–3014. CrossRef CAS Web of Science Google Scholar
Ibis, C. & Deniz, N. G. (2007). Acta Cryst. E63, o1091–o1092. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lednicer, D., Mitscher, L. A. & Georg, G. I. (1990). The Organic Chemistry of Drug Synthesis, Vol. 4, New York: J. Wiley & Sons. Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Rigaku/MSC (2006). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas. USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar