2-(1-Adamant­yl)-1,3-diphenyl­propan-2-ol

Babjaková, E.; Nečas, M.; Vícha, R.

doi:10.1107/S1600536810030047

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2175

https://doi.org/10.1107/S1600536810030047

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2-(1-Adamantyl)-1,3-diphenylpropan-2-ol

Eva Babjaková,^a Marek Nečas ^b and Robert Vícha ^a ^*

^aDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Nám. T. G. Masaryka 275, Zlín,762 72, Czech Republic, and ^bDepartment of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, Brno-Bohunice, 625 00, Czech Republic
^*Correspondence e-mail: rvicha@ft.utb.cz

(Received 19 July 2010; accepted 28 July 2010; online 31 July 2010)

In the title compound, C₂₅H₃₀O, the adamantane cage consists of three fused cyclohexane rings in classical chair conformations, with C—C—C angles in the range 107.15 (9)–111.55 (9)°. The dihedral angle between the benzene rings is 46.91 (4)° and the conformation is stabilized by a weak intramolecular C—H⋯π interaction.

Related literature

For the preparation and spectroscopic properties of the title compound, see: Vícha et al. (2006 ). For related structures, see: Vaissermann & Lomas (1997 ); Vícha & Nečas (2010 ).

Experimental

Crystal data

C₂₅H₃₀O
M_r = 346.49
Monoclinic, C 2/c
a = 24.2808 (10) Å
b = 6.3978 (2) Å
c = 25.2555 (14) Å
β = 106.183 (5)°
V = 3767.8 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 120 K
0.40 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.965, T_max = 1.000
17425 measured reflections
3315 independent reflections
2381 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.080
S = 0.96
3315 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C20–C25 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Cg1	0.95	2.70	3.3172 (13)	123

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810030047/zl2292sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030047/zl2292Isup2.hkl

checkCIF report

Comment top

In the title compound, both benzene rings (C13–C18 and C20–C25) are essentially planar with maximum deviations from their respective best planes of 0.0053 (12) Å for C17 and 0.0073 (12) Å for C25. The angle between the best planes of these rings is 46.97 (3)°. The torsion angles that describe the arrangement of the two benzyl substituents and the adamantane cage – C2—C1—C11—O1, C1—C11—C12—C13, C1—C11—C19—C20, C11—C12—C13—C14 and C11—C19—C20—C21 – are 63.42 (11)°, -134.29 (10)°, -174.22 (10)°, -104.43 (13)°, and 107.99 (13)°, respectively. The conformation of the molecules in the crystal is stabilized by a weak C—H···π interaction, C14—H14···Cg1 (Cg1 is the centre of gravity of C20–C25), with a C14···Cg1 distance of 3.3172 (13) Å (see Fig. 2 and Table 1). In analogy to the previously published structure of 1-adamantyl(diphenyl)methanol (Vícha & Nečas, 2010), no H-bonds were observed in the crystal packing. The shortest distance between two adjacent O-atoms is 4.7666 (11) Å. Surprisingly, the more strained molecules of di(1-adamantyl)(2,5-diisopropylphenyl)methanol with two bulky adamantane cages form O—H···O linked dimers in the solid state (Vaissermann & Lomas, 1997).

Related literature top

For the preparation and spectroscopic properties of the title compound, see: Vícha et al. (2006). For related structures, see: Vaissermann & Lomas (1997); Vícha & Nečas (2010).

Experimental top

The title compound was isolated from a complex mixture obtained from the reaction of adamantane-1-carbonyl chloride with benzylmagnesium chloride as described previously (Vícha et al., 2006). The crystal used for data collection was grown by slow evaporation of a solution in hexane at room temperature.

Structure description top

For the preparation and spectroscopic properties of the title compound, see: Vícha et al. (2006). For related structures, see: Vaissermann & Lomas (1997); Vícha & Nečas (2010).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Ellipsoid plot (50% probability) of the asymmetric unit. Hydrogen atoms are represented as spheres of arbitrary size.
	Fig. 2. Crystal packing viewed along the b-axis. Intramolecular C—H···π interactions are shown as dotted lines. Cg1 is the center of gravity of C20–C25. H-atoms (except those which are involved in C—H···π interactions) have been omitted for clarity.

2-(1-Adamantyl)-1,3-diphenylpropan-2-ol top

Crystal data top

C₂₅H₃₀O	F(000) = 1504
M_r = 346.49	D_x = 1.222 Mg m⁻³
Monoclinic, C2/c	Melting point: 396 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 24.2808 (10) Å	Cell parameters from 6762 reflections
b = 6.3978 (2) Å	θ = 3.0–27.2°
c = 25.2555 (14) Å	µ = 0.07 mm⁻¹
β = 106.183 (5)°	T = 120 K
V = 3767.8 (3) Å³	Block, colourless
Z = 8	0.40 × 0.30 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector	3315 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2381 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 8.4353 pixels mm^-1	θ_max = 25.0°, θ_min = 3.3°
ω scan	h = −28→28
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −7→7
T_min = 0.965, T_max = 1.000	l = −17→29
17425 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0466P)²] where P = (F_o² + 2F_c²)/3
3315 reflections	(Δ/σ)_max < 0.001
236 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₅H₃₀O	V = 3767.8 (3) Å³
M_r = 346.49	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.2808 (10) Å	µ = 0.07 mm⁻¹
b = 6.3978 (2) Å	T = 120 K
c = 25.2555 (14) Å	0.40 × 0.30 × 0.20 mm
β = 106.183 (5)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector	3315 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2381 reflections with I > 2σ(I)
T_min = 0.965, T_max = 1.000	R_int = 0.024
17425 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 0.96	Δρ_max = 0.20 e Å⁻³
3315 reflections	Δρ_min = −0.21 e Å⁻³
236 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 > 2σ(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	0.01323 (3)	0.97763 (12)	0.09694 (3)	0.0262 (2)
H1	0.0440	1.0301	0.1163	0.039*
C1	−0.05610 (5)	0.71728 (17)	0.10148 (5)	0.0194 (3)
C2	−0.08736 (5)	0.73762 (19)	0.03965 (5)	0.0238 (3)
H2A	−0.0807	0.8790	0.0268	0.029*
H2B	−0.0715	0.6344	0.0187	0.029*
C3	−0.15200 (5)	0.70122 (19)	0.02840 (5)	0.0251 (3)
H3	−0.1710	0.7147	−0.0120	0.030*
C4	−0.17747 (5)	0.86215 (19)	0.05970 (5)	0.0267 (3)
H4A	−0.1717	1.0049	0.0471	0.032*
H4B	−0.2192	0.8381	0.0525	0.032*
C5	−0.14785 (5)	0.84099 (17)	0.12124 (5)	0.0225 (3)
H5	−0.1640	0.9466	0.1420	0.027*
C6	−0.15777 (5)	0.62180 (17)	0.14074 (5)	0.0246 (3)
H6A	−0.1994	0.5969	0.1341	0.030*
H6B	−0.1391	0.6087	0.1808	0.030*
C7	−0.13269 (5)	0.46028 (18)	0.10926 (5)	0.0244 (3)
H7	−0.1395	0.3168	0.1218	0.029*
C8	−0.06786 (5)	0.49578 (17)	0.12020 (5)	0.0232 (3)
H8A	−0.0519	0.3902	0.0999	0.028*
H8B	−0.0487	0.4791	0.1600	0.028*
C9	−0.16199 (5)	0.48078 (19)	0.04750 (5)	0.0279 (3)
H9A	−0.2036	0.4547	0.0401	0.034*
H9B	−0.1461	0.3760	0.0269	0.034*
C10	−0.08327 (5)	0.87808 (17)	0.13238 (5)	0.0216 (3)
H10A	−0.0646	0.8674	0.1725	0.026*
H10B	−0.0767	1.0210	0.1204	0.026*
C11	0.00961 (5)	0.76258 (18)	0.11266 (5)	0.0212 (3)
C12	0.04245 (5)	0.72698 (18)	0.17460 (5)	0.0230 (3)
H12A	0.0137	0.7129	0.1956	0.028*
H12B	0.0631	0.5921	0.1776	0.028*
C13	0.08517 (5)	0.89325 (18)	0.20235 (5)	0.0221 (3)
C14	0.14410 (5)	0.8651 (2)	0.21349 (5)	0.0314 (3)
H14	0.1586	0.7389	0.2028	0.038*
C15	0.18185 (5)	1.0196 (2)	0.24008 (6)	0.0395 (4)
H15	0.2220	0.9986	0.2472	0.047*
C16	0.16163 (6)	1.2032 (2)	0.25620 (5)	0.0365 (4)
H16	0.1877	1.3086	0.2743	0.044*
C17	0.10354 (5)	1.2327 (2)	0.24588 (5)	0.0326 (3)
H17	0.0893	1.3582	0.2573	0.039*
C18	0.06578 (5)	1.08006 (18)	0.21888 (5)	0.0270 (3)
H18	0.0257	1.1033	0.2115	0.032*
C19	0.03612 (5)	0.62720 (19)	0.07513 (5)	0.0269 (3)
H19A	0.0262	0.4791	0.0792	0.032*
H19B	0.0183	0.6678	0.0363	0.032*
C20	0.10058 (5)	0.64448 (19)	0.08689 (5)	0.0246 (3)
C21	0.13650 (5)	0.4812 (2)	0.11175 (5)	0.0289 (3)
H21	0.1203	0.3564	0.1213	0.035*
C22	0.19554 (5)	0.4986 (2)	0.12276 (6)	0.0325 (3)
H22	0.2195	0.3857	0.1396	0.039*
C23	0.21958 (5)	0.6795 (2)	0.10939 (5)	0.0323 (3)
H23	0.2601	0.6922	0.1174	0.039*
C24	0.18452 (5)	0.8419 (2)	0.08428 (5)	0.0324 (3)
H24	0.2009	0.9664	0.0748	0.039*
C25	0.12569 (5)	0.8235 (2)	0.07287 (5)	0.0287 (3)
H25	0.1019	0.9355	0.0551	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0248 (5)	0.0256 (5)	0.0256 (5)	−0.0059 (4)	0.0027 (4)	0.0034 (4)
C1	0.0207 (6)	0.0180 (6)	0.0199 (7)	0.0004 (5)	0.0061 (5)	−0.0003 (5)
C2	0.0221 (6)	0.0273 (7)	0.0218 (8)	0.0001 (5)	0.0058 (6)	−0.0006 (6)
C3	0.0211 (6)	0.0317 (7)	0.0206 (8)	0.0003 (5)	0.0025 (5)	−0.0015 (6)
C4	0.0204 (6)	0.0260 (7)	0.0323 (8)	0.0034 (5)	0.0049 (6)	0.0029 (6)
C5	0.0221 (6)	0.0195 (6)	0.0272 (8)	0.0048 (5)	0.0092 (6)	−0.0014 (5)
C6	0.0197 (6)	0.0262 (7)	0.0293 (8)	0.0006 (5)	0.0091 (6)	0.0017 (6)
C7	0.0234 (6)	0.0168 (6)	0.0345 (8)	−0.0006 (5)	0.0105 (6)	0.0005 (6)
C8	0.0228 (6)	0.0199 (6)	0.0277 (8)	0.0022 (5)	0.0083 (6)	−0.0001 (6)
C9	0.0192 (6)	0.0286 (7)	0.0357 (9)	−0.0032 (5)	0.0072 (6)	−0.0099 (6)
C10	0.0233 (6)	0.0190 (6)	0.0225 (7)	0.0004 (5)	0.0065 (5)	0.0000 (5)
C11	0.0222 (6)	0.0209 (6)	0.0203 (7)	−0.0009 (5)	0.0057 (5)	0.0009 (5)
C12	0.0225 (6)	0.0236 (6)	0.0228 (7)	0.0016 (5)	0.0059 (5)	0.0004 (6)
C13	0.0244 (6)	0.0277 (7)	0.0138 (7)	0.0011 (5)	0.0047 (5)	0.0023 (5)
C14	0.0253 (7)	0.0422 (8)	0.0253 (8)	0.0041 (6)	0.0046 (6)	−0.0077 (7)
C15	0.0238 (7)	0.0638 (10)	0.0297 (9)	−0.0067 (7)	0.0054 (6)	−0.0108 (8)
C16	0.0416 (8)	0.0420 (8)	0.0241 (8)	−0.0154 (7)	0.0062 (7)	−0.0061 (7)
C17	0.0432 (8)	0.0280 (7)	0.0233 (8)	0.0000 (6)	0.0038 (6)	−0.0012 (6)
C18	0.0274 (7)	0.0306 (7)	0.0210 (8)	0.0036 (5)	0.0034 (6)	0.0006 (6)
C19	0.0221 (6)	0.0350 (7)	0.0240 (8)	−0.0010 (5)	0.0070 (6)	−0.0058 (6)
C20	0.0226 (6)	0.0337 (7)	0.0187 (7)	−0.0002 (5)	0.0076 (5)	−0.0076 (6)
C21	0.0299 (7)	0.0269 (7)	0.0323 (8)	0.0002 (5)	0.0126 (6)	−0.0065 (6)
C22	0.0274 (7)	0.0351 (8)	0.0346 (9)	0.0096 (6)	0.0082 (6)	−0.0060 (7)
C23	0.0193 (6)	0.0439 (8)	0.0338 (9)	0.0003 (6)	0.0077 (6)	−0.0077 (7)
C24	0.0283 (7)	0.0403 (8)	0.0313 (9)	−0.0021 (6)	0.0129 (6)	0.0021 (7)
C25	0.0256 (7)	0.0394 (8)	0.0224 (8)	0.0046 (6)	0.0086 (6)	0.0046 (6)

Geometric parameters (Å, º) top

O1—C11	1.4414 (13)	C11—C19	1.5500 (16)
O1—H1	0.8400	C11—C12	1.5620 (16)
C1—C2	1.5397 (16)	C12—C13	1.5144 (15)
C1—C8	1.5454 (15)	C12—H12A	0.9900
C1—C10	1.5459 (15)	C12—H12B	0.9900
C1—C11	1.5680 (15)	C13—C18	1.3906 (16)
C2—C3	1.5331 (15)	C13—C14	1.3910 (15)
C2—H2A	0.9900	C14—C15	1.3876 (17)
C2—H2B	0.9900	C14—H14	0.9500
C3—C4	1.5296 (16)	C15—C16	1.3774 (19)
C3—C9	1.5316 (17)	C15—H15	0.9500
C3—H3	1.0000	C16—C17	1.3741 (17)
C4—C5	1.5258 (17)	C16—H16	0.9500
C4—H4A	0.9900	C17—C18	1.3824 (17)
C4—H4B	0.9900	C17—H17	0.9500
C5—C6	1.5276 (15)	C18—H18	0.9500
C5—C10	1.5323 (15)	C19—C20	1.5136 (15)
C5—H5	1.0000	C19—H19A	0.9900
C6—C7	1.5299 (15)	C19—H19B	0.9900
C6—H6A	0.9900	C20—C25	1.3891 (16)
C6—H6B	0.9900	C20—C21	1.3929 (17)
C7—C9	1.5289 (17)	C21—C22	1.3866 (16)
C7—C8	1.5373 (15)	C21—H21	0.9500
C7—H7	1.0000	C22—C23	1.3798 (18)
C8—H8A	0.9900	C22—H22	0.9500
C8—H8B	0.9900	C23—C24	1.3801 (17)
C9—H9A	0.9900	C23—H23	0.9500
C9—H9B	0.9900	C24—C25	1.3812 (16)
C10—H10A	0.9900	C24—H24	0.9500
C10—H10B	0.9900	C25—H25	0.9500

C11—O1—H1	109.5	C5—C10—H10B	109.4
C2—C1—C8	107.87 (9)	C1—C10—H10B	109.4
C2—C1—C10	107.26 (9)	H10A—C10—H10B	108.0
C8—C1—C10	108.34 (9)	O1—C11—C19	107.30 (9)
C2—C1—C11	110.87 (9)	O1—C11—C12	111.20 (9)
C8—C1—C11	112.33 (9)	C19—C11—C12	110.36 (9)
C10—C1—C11	110.01 (9)	O1—C11—C1	105.31 (9)
C3—C2—C1	111.40 (9)	C19—C11—C1	111.21 (9)
C3—C2—H2A	109.3	C12—C11—C1	111.29 (9)
C1—C2—H2A	109.3	C13—C12—C11	116.98 (9)
C3—C2—H2B	109.3	C13—C12—H12A	108.1
C1—C2—H2B	109.3	C11—C12—H12A	108.1
H2A—C2—H2B	108.0	C13—C12—H12B	108.1
C4—C3—C9	109.56 (10)	C11—C12—H12B	108.0
C4—C3—C2	110.03 (10)	H12A—C12—H12B	107.3
C9—C3—C2	108.99 (9)	C18—C13—C14	117.77 (11)
C4—C3—H3	109.4	C18—C13—C12	119.81 (10)
C9—C3—H3	109.4	C14—C13—C12	122.40 (11)
C2—C3—H3	109.4	C15—C14—C13	120.59 (12)
C5—C4—C3	108.84 (9)	C15—C14—H14	119.7
C5—C4—H4A	109.9	C13—C14—H14	119.7
C3—C4—H4A	109.9	C16—C15—C14	120.59 (12)
C5—C4—H4B	109.9	C16—C15—H15	119.7
C3—C4—H4B	109.9	C14—C15—H15	119.7
H4A—C4—H4B	108.3	C17—C16—C15	119.53 (12)
C4—C5—C6	109.76 (10)	C17—C16—H16	120.2
C4—C5—C10	109.94 (10)	C15—C16—H16	120.2
C6—C5—C10	109.16 (9)	C16—C17—C18	120.06 (13)
C4—C5—H5	109.3	C16—C17—H17	120.0
C6—C5—H5	109.3	C18—C17—H17	120.0
C10—C5—H5	109.3	C17—C18—C13	121.46 (12)
C5—C6—C7	109.34 (9)	C17—C18—H18	119.3
C5—C6—H6A	109.8	C13—C18—H18	119.3
C7—C6—H6A	109.8	C20—C19—C11	114.97 (10)
C5—C6—H6B	109.8	C20—C19—H19A	108.5
C7—C6—H6B	109.8	C11—C19—H19A	108.5
H6A—C6—H6B	108.3	C20—C19—H19B	108.5
C9—C7—C6	109.44 (10)	C11—C19—H19B	108.5
C9—C7—C8	109.43 (10)	H19A—C19—H19B	107.5
C6—C7—C8	110.04 (10)	C25—C20—C21	117.97 (11)
C9—C7—H7	109.3	C25—C20—C19	120.90 (11)
C6—C7—H7	109.3	C21—C20—C19	121.13 (11)
C8—C7—H7	109.3	C22—C21—C20	120.84 (12)
C7—C8—C1	110.35 (9)	C22—C21—H21	119.6
C7—C8—H8A	109.6	C20—C21—H21	119.6
C1—C8—H8A	109.6	C23—C22—C21	120.17 (12)
C7—C8—H8B	109.6	C23—C22—H22	119.9
C1—C8—H8B	109.6	C21—C22—H22	119.9
H8A—C8—H8B	108.1	C22—C23—C24	119.65 (12)
C7—C9—C3	109.32 (9)	C22—C23—H23	120.2
C7—C9—H9A	109.8	C24—C23—H23	120.2
C3—C9—H9A	109.8	C23—C24—C25	120.11 (13)
C7—C9—H9B	109.8	C23—C24—H24	119.9
C3—C9—H9B	109.8	C25—C24—H24	119.9
H9A—C9—H9B	108.3	C24—C25—C20	121.25 (12)
C5—C10—C1	111.28 (9)	C24—C25—H25	119.4
C5—C10—H10A	109.4	C20—C25—H25	119.4
C1—C10—H10A	109.4

C8—C1—C2—C3	58.61 (12)	C8—C1—C11—C19	68.28 (13)
C10—C1—C2—C3	−57.89 (12)	C10—C1—C11—C19	−170.96 (10)
C11—C1—C2—C3	−178.01 (9)	C2—C1—C11—C12	−175.98 (9)
C1—C2—C3—C4	60.09 (13)	C8—C1—C11—C12	−55.21 (12)
C1—C2—C3—C9	−60.06 (12)	C10—C1—C11—C12	65.55 (12)
C9—C3—C4—C5	60.47 (12)	O1—C11—C12—C13	−17.22 (14)
C2—C3—C4—C5	−59.33 (12)	C19—C11—C12—C13	101.75 (11)
C3—C4—C5—C6	−60.57 (11)	C1—C11—C12—C13	−134.29 (10)
C3—C4—C5—C10	59.52 (12)	C11—C12—C13—C18	77.21 (14)
C4—C5—C6—C7	60.41 (12)	C11—C12—C13—C14	−104.43 (13)
C10—C5—C6—C7	−60.15 (13)	C18—C13—C14—C15	−0.20 (19)
C5—C6—C7—C9	−59.80 (12)	C12—C13—C14—C15	−178.59 (12)
C5—C6—C7—C8	60.48 (13)	C13—C14—C15—C16	0.4 (2)
C9—C7—C8—C1	60.66 (12)	C14—C15—C16—C17	0.1 (2)
C6—C7—C8—C1	−59.63 (13)	C15—C16—C17—C18	−0.8 (2)
C2—C1—C8—C7	−58.44 (12)	C16—C17—C18—C13	1.0 (2)
C10—C1—C8—C7	57.36 (12)	C14—C13—C18—C17	−0.49 (18)
C11—C1—C8—C7	179.08 (10)	C12—C13—C18—C17	177.94 (12)
C6—C7—C9—C3	59.81 (12)	O1—C11—C19—C20	71.11 (13)
C8—C7—C9—C3	−60.84 (12)	C12—C11—C19—C20	−50.21 (13)
C4—C3—C9—C7	−60.35 (12)	C1—C11—C19—C20	−174.22 (10)
C2—C3—C9—C7	60.09 (12)	C11—C19—C20—C25	−72.41 (15)
C4—C5—C10—C1	−60.40 (12)	C11—C19—C20—C21	107.99 (13)
C6—C5—C10—C1	60.05 (13)	C25—C20—C21—C22	0.84 (19)
C2—C1—C10—C5	58.06 (12)	C19—C20—C21—C22	−179.55 (11)
C8—C1—C10—C5	−58.14 (12)	C20—C21—C22—C23	0.34 (19)
C11—C1—C10—C5	178.72 (9)	C21—C22—C23—C24	−0.9 (2)
C2—C1—C11—O1	63.42 (11)	C22—C23—C24—C25	0.3 (2)
C8—C1—C11—O1	−175.82 (9)	C23—C24—C25—C20	0.9 (2)
C10—C1—C11—O1	−55.05 (12)	C21—C20—C25—C24	−1.47 (19)
C2—C1—C11—C19	−52.49 (12)	C19—C20—C25—C24	178.92 (11)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of C20–C25 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg1	0.95	2.70	3.3172 (13)	123

Experimental details

Crystal data
Chemical formula	C₂₅H₃₀O
M_r	346.49
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	120
a, b, c (Å)	24.2808 (10), 6.3978 (2), 25.2555 (14)
β (°)	106.183 (5)
V (Å³)	3767.8 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.965, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	17425, 3315, 2381
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.080, 0.96
No. of reflections	3315
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of C20–C25 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg1	0.95	2.70	3.3172 (13)	122.82

Acknowledgements

Financial support of this work by the Internal Founding Agency of Tomas Bata University in Zlin, project No. IGA/7/FT/10/D, is gratefully acknowledged.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vaissermann, J. & Lomas, J. S. (1997). Acta Cryst. C53, 1341–1343. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Vícha, R. & Nečas, M. (2010). Acta Cryst. E66, o1626. Web of Science CSD CrossRef IUCr Journals Google Scholar
Vícha, R., Nečas, M. & Potáček, M. (2006). Collect. Czech. Chem. Commun. 71, 709–722. Google Scholar

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