(1-Adamant­yl)diphenyl­methano­l

Vícha, R.; Nečas, M.

doi:10.1107/S1600536810021707

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1626

doi:10.1107/S1600536810021707

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(1-Adamantyl)diphenylmethanol

Robert Vícha ^a ^* and Marek Nečas ^b

^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 in Brno, Kamenice 5, Brno-Bohunice 625 00, Czech Republic
^*Correspondence e-mail: rvicha@ft.utb.cz

(Received 28 May 2010; accepted 7 June 2010; online 16 June 2010)

In the title compound, C₂₃H₂₆O, the adamantane cage consists of three fused cyclohexane rings in classical chair conformations with absolute values of the C—C—C angles in the range 106.57 (11)–111.56 (12)°. The dihedral angle between the two phenyl rings is 81.38 (4)°. Although a hydroxy group is present as a conceivable donor, no hydrogen bonds are observed in the crystal structure.

Related literature

For the preparation and spectroscopic properties of the title compound, see: Vícha et al. (2006 ); Stetter & Rauscher (1960 ); Molle et al. (1984 ). For related structures, see: Vaissermann & Lomas (1997 ).

Experimental

Crystal data

C₂₃H₂₆O
M_r = 318.44
Monoclinic, P 2₁ /n
a = 6.5370 (12) Å
b = 17.037 (3) Å
c = 15.322 (2) Å
β = 91.993 (14)°
V = 1705.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 120 K
0.40 × 0.40 × 0.30 mm

Data collection

Kuma KM-4-CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.971, T_max = 0.978
10354 measured reflections
2996 independent reflections
2133 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.095
S = 0.93
2996 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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: 10.1107/S1600536810021707/lh5059sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021707/lh5059Isup2.hkl

checkCIF report

Comment top

Adamantane derivatives are well known primarily for their unusual virustatic effect. Nevertheless, the scope of the biological activity of adamantane derivatives is much wider and novel compounds are prepared and tested steadily. The title tertiary alcohol was isolated as unwanted by-product accompanying 1-adamantyl phenyl ketone when no catalyst was employed. The molecule of title compound (Fig. 1) consists of two phenyl rings and an adamantane cage bound to a carbon atom to form a strained tertiary alcohol. Both phenyl rings (C12–C17 and C18–C23) are essentially planar with the maximum deviation from the best planes being 0.0110 (14) Å for C17 and 0.0027 (14) Å for C19. The angle between best planes of these rings is 81.38 (4)°. Both rings are slightly deformed in the plane owing to steric hindrance of the bulky adamantane moiety. The torsion angles describing arrangement of two phenyl rings and the adamantane cage C2—C1—C11—C12 and C1—C11—C12—C13 are -59.06 (14)° and -93.57 (15)°, respectively. Although a hydroxy group is present as a conceivable H-donor, no H-bonds were observed in crystal packing (see Fig. 2). The distance between the closest adjacent O-atoms is 5.2050 (17) Å.

Related literature top

For the preparation and spectroscopic properties of the title compound, see: Vícha et al. (2006); Stetter & Rauscher (1960); Molle et al. (1984). For related structures, see: Vaissermann & Lomas (1997).

Experimental top

Title compound was isolated from a complex mixture obtained by the reaction of adamantane-1-carbonyl chloride with phenylmagnesium bromide as it has been described previously (Vícha et al., 2006). The crystal used for data collection was grown by slow cooling of a saturated solution of title compound in n-hexane.

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. An ellipsoid plot (50% probability) of the asymmetric unit. Hydrogen atoms are represented as arbitrary spheres.
	Fig. 2. A crystal packing viewed along the a-axis. Hydrogen atoms are omitted for clarity.

(1-Adamantyl)diphenylmethanol top

Crystal data top

C₂₃H₂₆O	F(000) = 688
M_r = 318.44	D_x = 1.240 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 400 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 6.5370 (12) Å	Cell parameters from 10305 reflections
b = 17.037 (3) Å	θ = 3.1–27.1°
c = 15.322 (2) Å	µ = 0.07 mm⁻¹
β = 91.993 (14)°	T = 120 K
V = 1705.4 (5) Å³	Block, colourless
Z = 4	0.40 × 0.40 × 0.30 mm

Data collection top

Kuma KM-4-CCD diffractometer	2996 independent reflections
Radiation source: fine-focus sealed tube	2133 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 0.06 mm pixels mm^-1	θ_max = 25.0°, θ_min = 3.3°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −20→20
T_min = 0.971, T_max = 0.978	l = −15→18
10354 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ²(F_o²) + (0.0571P)²] where P = (F_o² + 2F_c²)/3
2996 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₃H₂₆O	V = 1705.4 (5) Å³
M_r = 318.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.5370 (12) Å	µ = 0.07 mm⁻¹
b = 17.037 (3) Å	T = 120 K
c = 15.322 (2) Å	0.40 × 0.40 × 0.30 mm
β = 91.993 (14)°

Data collection top

Kuma KM-4-CCD diffractometer	2996 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2133 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.978	R_int = 0.027
10354 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	Δρ_max = 0.21 e Å⁻³
2996 reflections	Δρ_min = −0.18 e Å⁻³
221 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	0.20822 (14)	0.62332 (7)	0.54962 (6)	0.0238 (3)
C1	−0.0671 (2)	0.63609 (8)	0.65477 (9)	0.0192 (3)
C2	−0.2658 (2)	0.67842 (8)	0.68106 (9)	0.0215 (3)
H2A	−0.2439	0.7359	0.6801	0.026*
H2B	−0.3779	0.6657	0.6383	0.026*
C3	−0.3275 (2)	0.65309 (8)	0.77314 (9)	0.0249 (3)
H3	−0.4570	0.6805	0.7881	0.030*
C4	−0.1578 (2)	0.67522 (9)	0.84012 (10)	0.0297 (4)
H4A	−0.1979	0.6597	0.8994	0.036*
H4B	−0.1357	0.7327	0.8396	0.036*
C5	0.0398 (2)	0.63284 (9)	0.81687 (9)	0.0287 (4)
H5	0.1516	0.6474	0.8601	0.034*
C6	0.0060 (2)	0.54372 (9)	0.81919 (10)	0.0326 (4)
H6A	0.1342	0.5162	0.8053	0.039*
H6B	−0.0334	0.5275	0.8783	0.039*
C7	−0.1637 (2)	0.52169 (9)	0.75231 (10)	0.0275 (4)
H7	−0.1866	0.4637	0.7537	0.033*
C8	−0.0988 (2)	0.54619 (8)	0.66034 (9)	0.0239 (3)
H8A	−0.2055	0.5299	0.6166	0.029*
H8B	0.0301	0.5191	0.6465	0.029*
C9	−0.3624 (2)	0.56423 (9)	0.77457 (10)	0.0278 (4)
H9A	−0.4726	0.5500	0.7315	0.033*
H9B	−0.4054	0.5479	0.8332	0.033*
C10	0.1005 (2)	0.65811 (9)	0.72486 (9)	0.0241 (3)
H10A	0.2308	0.6323	0.7105	0.029*
H10B	0.1228	0.7156	0.7241	0.029*
C11	0.0093 (2)	0.66125 (8)	0.56147 (9)	0.0195 (3)
C12	0.0501 (2)	0.75000 (8)	0.55950 (8)	0.0202 (3)
C13	0.2443 (2)	0.78085 (8)	0.57812 (9)	0.0235 (3)
H13	0.3561	0.7463	0.5898	0.028*
C14	0.2764 (2)	0.86159 (9)	0.57982 (9)	0.0270 (4)
H14	0.4097	0.8817	0.5925	0.032*
C15	0.1154 (2)	0.91283 (9)	0.56323 (9)	0.0288 (4)
H15	0.1373	0.9679	0.5655	0.035*
C16	−0.0776 (2)	0.88315 (9)	0.54334 (10)	0.0292 (4)
H16	−0.1885	0.9180	0.5315	0.035*
C17	−0.1100 (2)	0.80241 (8)	0.54063 (9)	0.0247 (3)
H17	−0.2426	0.7827	0.5258	0.030*
C18	−0.1246 (2)	0.64101 (8)	0.47894 (9)	0.0211 (3)
C19	−0.0360 (2)	0.65919 (8)	0.39898 (9)	0.0245 (3)
H19	0.0992	0.6797	0.3993	0.029*
C20	−0.1413 (2)	0.64783 (8)	0.31960 (9)	0.0274 (4)
H20	−0.0782	0.6610	0.2666	0.033*
C21	−0.3378 (2)	0.61734 (9)	0.31742 (10)	0.0292 (4)
H21	−0.4101	0.6092	0.2633	0.035*
C22	−0.4266 (2)	0.59892 (9)	0.39521 (10)	0.0308 (4)
H22	−0.5614	0.5780	0.3943	0.037*
C23	−0.3220 (2)	0.61044 (9)	0.47534 (9)	0.0263 (4)
H23	−0.3865	0.5972	0.5280	0.032*
H1O	0.191 (3)	0.5765 (11)	0.5483 (11)	0.048 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0194 (5)	0.0248 (7)	0.0275 (6)	0.0000 (4)	0.0027 (4)	0.0009 (5)
C1	0.0199 (7)	0.0181 (8)	0.0197 (8)	0.0010 (6)	−0.0001 (6)	0.0011 (6)
C2	0.0228 (8)	0.0205 (8)	0.0212 (8)	0.0009 (6)	0.0012 (6)	0.0013 (6)
C3	0.0262 (8)	0.0255 (8)	0.0232 (8)	0.0028 (6)	0.0053 (6)	0.0020 (6)
C4	0.0374 (9)	0.0331 (9)	0.0189 (8)	−0.0015 (7)	0.0059 (7)	0.0013 (7)
C5	0.0303 (9)	0.0349 (9)	0.0204 (8)	−0.0023 (7)	−0.0042 (7)	0.0039 (7)
C6	0.0335 (9)	0.0373 (10)	0.0272 (9)	0.0060 (7)	0.0029 (7)	0.0131 (7)
C7	0.0314 (9)	0.0193 (8)	0.0322 (9)	0.0004 (6)	0.0048 (7)	0.0063 (6)
C8	0.0232 (8)	0.0215 (8)	0.0270 (8)	0.0010 (6)	0.0023 (6)	0.0012 (6)
C9	0.0291 (9)	0.0281 (9)	0.0265 (9)	−0.0014 (6)	0.0054 (7)	0.0056 (7)
C10	0.0227 (8)	0.0265 (9)	0.0229 (8)	−0.0006 (6)	−0.0015 (6)	0.0021 (6)
C11	0.0175 (7)	0.0206 (8)	0.0204 (8)	0.0013 (6)	0.0009 (6)	0.0000 (6)
C12	0.0245 (8)	0.0215 (8)	0.0146 (7)	−0.0016 (6)	0.0019 (6)	0.0002 (6)
C13	0.0255 (8)	0.0264 (9)	0.0185 (8)	−0.0014 (6)	−0.0003 (6)	0.0015 (6)
C14	0.0321 (9)	0.0304 (9)	0.0185 (8)	−0.0098 (7)	−0.0004 (6)	−0.0005 (6)
C15	0.0441 (10)	0.0206 (8)	0.0218 (8)	−0.0056 (7)	0.0035 (7)	−0.0001 (6)
C16	0.0370 (9)	0.0233 (9)	0.0274 (9)	0.0032 (7)	0.0023 (7)	0.0042 (6)
C17	0.0253 (8)	0.0244 (9)	0.0244 (8)	−0.0011 (6)	0.0011 (6)	0.0029 (6)
C18	0.0252 (8)	0.0173 (8)	0.0208 (8)	0.0013 (6)	−0.0003 (6)	−0.0018 (6)
C19	0.0273 (8)	0.0216 (8)	0.0247 (8)	−0.0017 (6)	0.0027 (6)	0.0007 (6)
C20	0.0401 (9)	0.0236 (8)	0.0187 (8)	0.0016 (7)	0.0032 (7)	0.0003 (6)
C21	0.0357 (9)	0.0302 (9)	0.0214 (8)	0.0010 (7)	−0.0048 (7)	−0.0038 (7)
C22	0.0283 (9)	0.0337 (9)	0.0300 (9)	−0.0060 (7)	−0.0035 (7)	−0.0048 (7)
C23	0.0261 (8)	0.0297 (9)	0.0231 (8)	−0.0033 (7)	0.0025 (6)	−0.0009 (6)

Geometric parameters (Å, º) top

O1—C11	1.4693 (16)	C9—H9B	0.9900
O1—H1O	0.806 (18)	C10—H10A	0.9900
C1—C8	1.5482 (19)	C10—H10B	0.9900
C1—C2	1.5507 (18)	C11—C12	1.5357 (19)
C1—C10	1.5535 (18)	C11—C18	1.5513 (19)
C1—C11	1.5895 (18)	C12—C13	1.3942 (18)
C2—C3	1.5425 (18)	C12—C17	1.3986 (19)
C2—H2A	0.9900	C13—C14	1.3915 (19)
C2—H2B	0.9900	C13—H13	0.9500
C3—C9	1.531 (2)	C14—C15	1.384 (2)
C3—C4	1.532 (2)	C14—H14	0.9500
C3—H3	1.0000	C15—C16	1.383 (2)
C4—C5	1.532 (2)	C15—H15	0.9500
C4—H4A	0.9900	C16—C17	1.392 (2)
C4—H4B	0.9900	C16—H16	0.9500
C5—C6	1.535 (2)	C17—H17	0.9500
C5—C10	1.5393 (19)	C18—C23	1.3906 (19)
C5—H5	1.0000	C18—C19	1.4079 (19)
C6—C7	1.530 (2)	C19—C20	1.3901 (19)
C6—H6A	0.9900	C19—H19	0.9500
C6—H6B	0.9900	C20—C21	1.385 (2)
C7—C9	1.536 (2)	C20—H20	0.9500
C7—C8	1.5434 (19)	C21—C22	1.380 (2)
C7—H7	1.0000	C21—H21	0.9500
C8—H8A	0.9900	C22—C23	1.399 (2)
C8—H8B	0.9900	C22—H22	0.9500
C9—H9A	0.9900	C23—H23	0.9500

C11—O1—H1O	108.3 (13)	C3—C9—H9B	109.7
C8—C1—C2	109.33 (11)	C7—C9—H9B	109.7
C8—C1—C10	107.05 (11)	H9A—C9—H9B	108.2
C2—C1—C10	106.57 (11)	C5—C10—C1	111.56 (12)
C8—C1—C11	111.29 (10)	C5—C10—H10A	109.3
C2—C1—C11	113.60 (11)	C1—C10—H10A	109.3
C10—C1—C11	108.69 (11)	C5—C10—H10B	109.3
C3—C2—C1	110.83 (11)	C1—C10—H10B	109.3
C3—C2—H2A	109.5	H10A—C10—H10B	108.0
C1—C2—H2A	109.5	O1—C11—C12	105.98 (11)
C3—C2—H2B	109.5	O1—C11—C18	106.15 (10)
C1—C2—H2B	109.5	C12—C11—C18	107.24 (10)
H2A—C2—H2B	108.1	O1—C11—C1	107.44 (10)
C9—C3—C4	109.77 (12)	C12—C11—C1	110.09 (10)
C9—C3—C2	109.48 (11)	C18—C11—C1	119.16 (11)
C4—C3—C2	109.72 (12)	C13—C12—C17	118.12 (13)
C9—C3—H3	109.3	C13—C12—C11	121.66 (12)
C4—C3—H3	109.3	C17—C12—C11	120.21 (12)
C2—C3—H3	109.3	C14—C13—C12	120.80 (14)
C3—C4—C5	108.96 (12)	C14—C13—H13	119.6
C3—C4—H4A	109.9	C12—C13—H13	119.6
C5—C4—H4A	109.9	C15—C14—C13	120.47 (14)
C3—C4—H4B	109.9	C15—C14—H14	119.8
C5—C4—H4B	109.9	C13—C14—H14	119.8
H4A—C4—H4B	108.3	C16—C15—C14	119.45 (14)
C4—C5—C6	109.72 (12)	C16—C15—H15	120.3
C4—C5—C10	109.11 (12)	C14—C15—H15	120.3
C6—C5—C10	109.86 (12)	C15—C16—C17	120.31 (14)
C4—C5—H5	109.4	C15—C16—H16	119.8
C6—C5—H5	109.4	C17—C16—H16	119.8
C10—C5—H5	109.4	C16—C17—C12	120.82 (13)
C7—C6—C5	109.20 (12)	C16—C17—H17	119.6
C7—C6—H6A	109.8	C12—C17—H17	119.6
C5—C6—H6A	109.8	C23—C18—C19	117.20 (13)
C7—C6—H6B	109.8	C23—C18—C11	127.72 (13)
C5—C6—H6B	109.8	C19—C18—C11	115.02 (12)
H6A—C6—H6B	108.3	C20—C19—C18	121.63 (14)
C6—C7—C9	109.53 (12)	C20—C19—H19	119.2
C6—C7—C8	109.22 (12)	C18—C19—H19	119.2
C9—C7—C8	109.67 (11)	C21—C20—C19	120.27 (14)
C6—C7—H7	109.5	C21—C20—H20	119.9
C9—C7—H7	109.5	C19—C20—H20	119.9
C8—C7—H7	109.5	C22—C21—C20	118.85 (14)
C7—C8—C1	111.07 (11)	C22—C21—H21	120.6
C7—C8—H8A	109.4	C20—C21—H21	120.6
C1—C8—H8A	109.4	C21—C22—C23	121.22 (14)
C7—C8—H8B	109.4	C21—C22—H22	119.4
C1—C8—H8B	109.4	C23—C22—H22	119.4
H8A—C8—H8B	108.0	C18—C23—C22	120.82 (14)
C3—C9—C7	109.63 (12)	C18—C23—H23	119.6
C3—C9—H9A	109.7	C22—C23—H23	119.6
C7—C9—H9A	109.7

Experimental details

Crystal data
Chemical formula	C₂₃H₂₆O
M_r	318.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	6.5370 (12), 17.037 (3), 15.322 (2)
β (°)	91.993 (14)
V (Å³)	1705.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.40 × 0.40 × 0.30

Data collection
Diffractometer	Kuma KM-4-CCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.971, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	10354, 2996, 2133
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.095, 0.93
No. of reflections	2996
No. of parameters	221
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.18

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

Acknowledgements

The financial support of this work by the Czech Ministry of Education, project No. MSM 7088352101, and by the Tomas Bata Foundation is gratefully acknowledged.

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