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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2175.
Published online 2010 July 31. doi:  10.1107/S1600536810030047
PMCID: PMC3007431

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

Abstract

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 [triangle]). For related structures, see: Vaissermann & Lomas (1997 [triangle]); Vícha & Nečas (2010 [triangle]).

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Object name is e-66-o2175-scheme1.jpg

Experimental

Crystal data

  • C25H30O
  • M r = 346.49
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2175-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.080
  • S = 0.96
  • 3315 reflections
  • 236 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.21 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030047/zl2292Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

Hydrogen atoms were positioned geometrically and refined as riding using standard SHELXTL constraints, with their Uiso values set to 1.2Ueq of that of their parent atoms.

Figures

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 ...

Crystal data

C25H30OF(000) = 1504
Mr = 346.49Dx = 1.222 Mg m3
Monoclinic, C2/cMelting point: 396 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 24.2808 (10) ÅCell parameters from 6762 reflections
b = 6.3978 (2) Åθ = 3.0–27.2°
c = 25.2555 (14) ŵ = 0.07 mm1
β = 106.183 (5)°T = 120 K
V = 3767.8 (3) Å3Block, colourless
Z = 80.40 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector3315 independent reflections
Radiation source: Enhance (Mo) X-ray Source2381 reflections with I > 2σ(I)
graphiteRint = 0.024
Detector resolution: 8.4353 pixels mm-1θmax = 25.0°, θmin = 3.3°
ω scanh = −28→28
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)k = −7→7
Tmin = 0.965, Tmax = 1.000l = −17→29
17425 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 0.96w = 1/[σ2(Fo2) + (0.0466P)2] where P = (Fo2 + 2Fc2)/3
3315 reflections(Δ/σ)max < 0.001
236 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.20 e Å3

Special details

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)

xyzUiso*/Ueq
O10.01323 (3)0.97763 (12)0.09694 (3)0.0262 (2)
H10.04401.03010.11630.039*
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−0.08070.87900.02680.029*
H2B−0.07150.63440.01870.029*
C3−0.15200 (5)0.70122 (19)0.02840 (5)0.0251 (3)
H3−0.17100.7147−0.01200.030*
C4−0.17747 (5)0.86215 (19)0.05970 (5)0.0267 (3)
H4A−0.17171.00490.04710.032*
H4B−0.21920.83810.05250.032*
C5−0.14785 (5)0.84099 (17)0.12124 (5)0.0225 (3)
H5−0.16400.94660.14200.027*
C6−0.15777 (5)0.62180 (17)0.14074 (5)0.0246 (3)
H6A−0.19940.59690.13410.030*
H6B−0.13910.60870.18080.030*
C7−0.13269 (5)0.46028 (18)0.10926 (5)0.0244 (3)
H7−0.13950.31680.12180.029*
C8−0.06786 (5)0.49578 (17)0.12020 (5)0.0232 (3)
H8A−0.05190.39020.09990.028*
H8B−0.04870.47910.16000.028*
C9−0.16199 (5)0.48078 (19)0.04750 (5)0.0279 (3)
H9A−0.20360.45470.04010.034*
H9B−0.14610.37600.02690.034*
C10−0.08327 (5)0.87808 (17)0.13238 (5)0.0216 (3)
H10A−0.06460.86740.17250.026*
H10B−0.07671.02100.12040.026*
C110.00961 (5)0.76258 (18)0.11266 (5)0.0212 (3)
C120.04245 (5)0.72698 (18)0.17460 (5)0.0230 (3)
H12A0.01370.71290.19560.028*
H12B0.06310.59210.17760.028*
C130.08517 (5)0.89325 (18)0.20235 (5)0.0221 (3)
C140.14410 (5)0.8651 (2)0.21349 (5)0.0314 (3)
H140.15860.73890.20280.038*
C150.18185 (5)1.0196 (2)0.24008 (6)0.0395 (4)
H150.22200.99860.24720.047*
C160.16163 (6)1.2032 (2)0.25620 (5)0.0365 (4)
H160.18771.30860.27430.044*
C170.10354 (5)1.2327 (2)0.24588 (5)0.0326 (3)
H170.08931.35820.25730.039*
C180.06578 (5)1.08006 (18)0.21888 (5)0.0270 (3)
H180.02571.10330.21150.032*
C190.03612 (5)0.62720 (19)0.07513 (5)0.0269 (3)
H19A0.02620.47910.07920.032*
H19B0.01830.66780.03630.032*
C200.10058 (5)0.64448 (19)0.08689 (5)0.0246 (3)
C210.13650 (5)0.4812 (2)0.11175 (5)0.0289 (3)
H210.12030.35640.12130.035*
C220.19554 (5)0.4986 (2)0.12276 (6)0.0325 (3)
H220.21950.38570.13960.039*
C230.21958 (5)0.6795 (2)0.10939 (5)0.0323 (3)
H230.26010.69220.11740.039*
C240.18452 (5)0.8419 (2)0.08428 (5)0.0324 (3)
H240.20090.96640.07480.039*
C250.12569 (5)0.8235 (2)0.07287 (5)0.0287 (3)
H250.10190.93550.05510.034*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0248 (5)0.0256 (5)0.0256 (5)−0.0059 (4)0.0027 (4)0.0034 (4)
C10.0207 (6)0.0180 (6)0.0199 (7)0.0004 (5)0.0061 (5)−0.0003 (5)
C20.0221 (6)0.0273 (7)0.0218 (8)0.0001 (5)0.0058 (6)−0.0006 (6)
C30.0211 (6)0.0317 (7)0.0206 (8)0.0003 (5)0.0025 (5)−0.0015 (6)
C40.0204 (6)0.0260 (7)0.0323 (8)0.0034 (5)0.0049 (6)0.0029 (6)
C50.0221 (6)0.0195 (6)0.0272 (8)0.0048 (5)0.0092 (6)−0.0014 (5)
C60.0197 (6)0.0262 (7)0.0293 (8)0.0006 (5)0.0091 (6)0.0017 (6)
C70.0234 (6)0.0168 (6)0.0345 (8)−0.0006 (5)0.0105 (6)0.0005 (6)
C80.0228 (6)0.0199 (6)0.0277 (8)0.0022 (5)0.0083 (6)−0.0001 (6)
C90.0192 (6)0.0286 (7)0.0357 (9)−0.0032 (5)0.0072 (6)−0.0099 (6)
C100.0233 (6)0.0190 (6)0.0225 (7)0.0004 (5)0.0065 (5)0.0000 (5)
C110.0222 (6)0.0209 (6)0.0203 (7)−0.0009 (5)0.0057 (5)0.0009 (5)
C120.0225 (6)0.0236 (6)0.0228 (7)0.0016 (5)0.0059 (5)0.0004 (6)
C130.0244 (6)0.0277 (7)0.0138 (7)0.0011 (5)0.0047 (5)0.0023 (5)
C140.0253 (7)0.0422 (8)0.0253 (8)0.0041 (6)0.0046 (6)−0.0077 (7)
C150.0238 (7)0.0638 (10)0.0297 (9)−0.0067 (7)0.0054 (6)−0.0108 (8)
C160.0416 (8)0.0420 (8)0.0241 (8)−0.0154 (7)0.0062 (7)−0.0061 (7)
C170.0432 (8)0.0280 (7)0.0233 (8)0.0000 (6)0.0038 (6)−0.0012 (6)
C180.0274 (7)0.0306 (7)0.0210 (8)0.0036 (5)0.0034 (6)0.0006 (6)
C190.0221 (6)0.0350 (7)0.0240 (8)−0.0010 (5)0.0070 (6)−0.0058 (6)
C200.0226 (6)0.0337 (7)0.0187 (7)−0.0002 (5)0.0076 (5)−0.0076 (6)
C210.0299 (7)0.0269 (7)0.0323 (8)0.0002 (5)0.0126 (6)−0.0065 (6)
C220.0274 (7)0.0351 (8)0.0346 (9)0.0096 (6)0.0082 (6)−0.0060 (7)
C230.0193 (6)0.0439 (8)0.0338 (9)0.0003 (6)0.0077 (6)−0.0077 (7)
C240.0283 (7)0.0403 (8)0.0313 (9)−0.0021 (6)0.0129 (6)0.0021 (7)
C250.0256 (7)0.0394 (8)0.0224 (8)0.0046 (6)0.0086 (6)0.0046 (6)

Geometric parameters (Å, °)

O1—C111.4414 (13)C11—C191.5500 (16)
O1—H10.8400C11—C121.5620 (16)
C1—C21.5397 (16)C12—C131.5144 (15)
C1—C81.5454 (15)C12—H12A0.9900
C1—C101.5459 (15)C12—H12B0.9900
C1—C111.5680 (15)C13—C181.3906 (16)
C2—C31.5331 (15)C13—C141.3910 (15)
C2—H2A0.9900C14—C151.3876 (17)
C2—H2B0.9900C14—H140.9500
C3—C41.5296 (16)C15—C161.3774 (19)
C3—C91.5316 (17)C15—H150.9500
C3—H31.0000C16—C171.3741 (17)
C4—C51.5258 (17)C16—H160.9500
C4—H4A0.9900C17—C181.3824 (17)
C4—H4B0.9900C17—H170.9500
C5—C61.5276 (15)C18—H180.9500
C5—C101.5323 (15)C19—C201.5136 (15)
C5—H51.0000C19—H19A0.9900
C6—C71.5299 (15)C19—H19B0.9900
C6—H6A0.9900C20—C251.3891 (16)
C6—H6B0.9900C20—C211.3929 (17)
C7—C91.5289 (17)C21—C221.3866 (16)
C7—C81.5373 (15)C21—H210.9500
C7—H71.0000C22—C231.3798 (18)
C8—H8A0.9900C22—H220.9500
C8—H8B0.9900C23—C241.3801 (17)
C9—H9A0.9900C23—H230.9500
C9—H9B0.9900C24—C251.3812 (16)
C10—H10A0.9900C24—H240.9500
C10—H10B0.9900C25—H250.9500
C11—O1—H1109.5C5—C10—H10B109.4
C2—C1—C8107.87 (9)C1—C10—H10B109.4
C2—C1—C10107.26 (9)H10A—C10—H10B108.0
C8—C1—C10108.34 (9)O1—C11—C19107.30 (9)
C2—C1—C11110.87 (9)O1—C11—C12111.20 (9)
C8—C1—C11112.33 (9)C19—C11—C12110.36 (9)
C10—C1—C11110.01 (9)O1—C11—C1105.31 (9)
C3—C2—C1111.40 (9)C19—C11—C1111.21 (9)
C3—C2—H2A109.3C12—C11—C1111.29 (9)
C1—C2—H2A109.3C13—C12—C11116.98 (9)
C3—C2—H2B109.3C13—C12—H12A108.1
C1—C2—H2B109.3C11—C12—H12A108.1
H2A—C2—H2B108.0C13—C12—H12B108.1
C4—C3—C9109.56 (10)C11—C12—H12B108.0
C4—C3—C2110.03 (10)H12A—C12—H12B107.3
C9—C3—C2108.99 (9)C18—C13—C14117.77 (11)
C4—C3—H3109.4C18—C13—C12119.81 (10)
C9—C3—H3109.4C14—C13—C12122.40 (11)
C2—C3—H3109.4C15—C14—C13120.59 (12)
C5—C4—C3108.84 (9)C15—C14—H14119.7
C5—C4—H4A109.9C13—C14—H14119.7
C3—C4—H4A109.9C16—C15—C14120.59 (12)
C5—C4—H4B109.9C16—C15—H15119.7
C3—C4—H4B109.9C14—C15—H15119.7
H4A—C4—H4B108.3C17—C16—C15119.53 (12)
C4—C5—C6109.76 (10)C17—C16—H16120.2
C4—C5—C10109.94 (10)C15—C16—H16120.2
C6—C5—C10109.16 (9)C16—C17—C18120.06 (13)
C4—C5—H5109.3C16—C17—H17120.0
C6—C5—H5109.3C18—C17—H17120.0
C10—C5—H5109.3C17—C18—C13121.46 (12)
C5—C6—C7109.34 (9)C17—C18—H18119.3
C5—C6—H6A109.8C13—C18—H18119.3
C7—C6—H6A109.8C20—C19—C11114.97 (10)
C5—C6—H6B109.8C20—C19—H19A108.5
C7—C6—H6B109.8C11—C19—H19A108.5
H6A—C6—H6B108.3C20—C19—H19B108.5
C9—C7—C6109.44 (10)C11—C19—H19B108.5
C9—C7—C8109.43 (10)H19A—C19—H19B107.5
C6—C7—C8110.04 (10)C25—C20—C21117.97 (11)
C9—C7—H7109.3C25—C20—C19120.90 (11)
C6—C7—H7109.3C21—C20—C19121.13 (11)
C8—C7—H7109.3C22—C21—C20120.84 (12)
C7—C8—C1110.35 (9)C22—C21—H21119.6
C7—C8—H8A109.6C20—C21—H21119.6
C1—C8—H8A109.6C23—C22—C21120.17 (12)
C7—C8—H8B109.6C23—C22—H22119.9
C1—C8—H8B109.6C21—C22—H22119.9
H8A—C8—H8B108.1C22—C23—C24119.65 (12)
C7—C9—C3109.32 (9)C22—C23—H23120.2
C7—C9—H9A109.8C24—C23—H23120.2
C3—C9—H9A109.8C23—C24—C25120.11 (13)
C7—C9—H9B109.8C23—C24—H24119.9
C3—C9—H9B109.8C25—C24—H24119.9
H9A—C9—H9B108.3C24—C25—C20121.25 (12)
C5—C10—C1111.28 (9)C24—C25—H25119.4
C5—C10—H10A109.4C20—C25—H25119.4
C1—C10—H10A109.4
C8—C1—C2—C358.61 (12)C8—C1—C11—C1968.28 (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—C460.09 (13)C8—C1—C11—C12−55.21 (12)
C1—C2—C3—C9−60.06 (12)C10—C1—C11—C1265.55 (12)
C9—C3—C4—C560.47 (12)O1—C11—C12—C13−17.22 (14)
C2—C3—C4—C5−59.33 (12)C19—C11—C12—C13101.75 (11)
C3—C4—C5—C6−60.57 (11)C1—C11—C12—C13−134.29 (10)
C3—C4—C5—C1059.52 (12)C11—C12—C13—C1877.21 (14)
C4—C5—C6—C760.41 (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—C860.48 (13)C13—C14—C15—C160.4 (2)
C9—C7—C8—C160.66 (12)C14—C15—C16—C170.1 (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—C131.0 (2)
C10—C1—C8—C757.36 (12)C14—C13—C18—C17−0.49 (18)
C11—C1—C8—C7179.08 (10)C12—C13—C18—C17177.94 (12)
C6—C7—C9—C359.81 (12)O1—C11—C19—C2071.11 (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—C760.09 (12)C11—C19—C20—C25−72.41 (15)
C4—C5—C10—C1−60.40 (12)C11—C19—C20—C21107.99 (13)
C6—C5—C10—C160.05 (13)C25—C20—C21—C220.84 (19)
C2—C1—C10—C558.06 (12)C19—C20—C21—C22−179.55 (11)
C8—C1—C10—C5−58.14 (12)C20—C21—C22—C230.34 (19)
C11—C1—C10—C5178.72 (9)C21—C22—C23—C24−0.9 (2)
C2—C1—C11—O163.42 (11)C22—C23—C24—C250.3 (2)
C8—C1—C11—O1−175.82 (9)C23—C24—C25—C200.9 (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—C24178.92 (11)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C20–C25 ring.
D—H···AD—HH···AD···AD—H···A
C14—H14···Cg10.952.703.3172 (13)123

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2292).

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