organic compounds
2-(Adamantan-1-yl)-1,3-bis(4-methylphenyl)propan-2-ol
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
The conformation of the title compound, C27H34O, is stabilized by a weak intramolecular C—H⋯π interaction. The dihedral angle between the benzene rings is 54.79 (4)°. The adamantane cage consists of three fused cyclohexane rings in classical chair conformations, with C—C—C angles in the range 107.75 (10)–111.35 (9)°. Although the molecule contains a hydroxy group as a conceivable hydrogen-bond donor, this group is sterically hindered by bulky substituents and no hydrogen bonds are observed in the crystal structure.
Related literature
For the preparation of the title compound, see: Vícha et al. (2006). For other examples of sterically shielded see: Babjaková et al. (2010); Vícha & Nečas (2010). For the structure of a related molecule which does form a hydrogen-bonded dimer in the solid state, see: Vaissermann & Lomas (1997).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536812050647/nk2194sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812050647/nk2194Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812050647/nk2194Isup3.cml
The title compound was isolated from complex mixture obtained from the reaction of adamantane-1-carbonyl chloride with 4-methylbenzylmagnesium chloride in diethyl ether as described previously (Vícha et al., 2006). The crystal used for data collection was grown by slow evaporation of an n-hexane solution at room temperature.
All carbon bound H atoms were placed at calculated positions and were refined as riding with their Uiso set to either 1.2Ueq or 1.5Ueq (methyl) of the respective carrier atoms; in addition, the methyl H atoms were allowed to rotate about the C—C bond. Oxygen bound H atom was located in a difference Fourier map and refined isotropically with the Uiso set to 1.5Ueq of the carrier atom.
The title molecule consists of two p-methylated benzene rings, the adamantane cage and propane-2-ol backbone to form a strained tertiary alcohol (Fig. 1). Both benzene rings are essentially planar with maximum deviations from their least squares best planes of 0.0013 (14) Å for C16 and 0.0138 (14) Å for C36, respectively. The dihedral angle between these best planes is 54.79 (4)°. The torsion angles C20—C2—C3—C31, C20—C2—C1—C11, C2—C1—C11—C12, C2—C3—C31—C32 and C21—C20—C2—O2 are -174.97 (10), -129.54 (11), -97.69 (15), 104.62 (14) and 61.95 (12)°, respectively. The conformation of the molecules in the solid state is stabilized by a weak C—H···π interaction, C12—H12···Cg1 (Cg1 is the centre of gravity of C31–C36), with a C12–Cg1 distance of 3.3576 (12) Å (Fig. 2, Table 1). In contrast to the more strained molecules of di(1-adamantyl)(2,5-diisopropylphenyl)methanol those form H-bonded dimers in the solid state (Vaissermann & Lomas, 1997), no H-bonds were observed in the crystal packing of the title compound. The shortest distance between two adjacent O-atoms is 4.6340 (13) Å (Fig. 2). Some other examples of such sterically shielded have been previously published (Babjaková et al., 2010; Vícha & Nečas, 2010).
For the preparation of the title compound, see:Vícha et al. (2006). For other examples of sterically shielded
see: Babjaková et al. (2010); Vícha & Nečas (2010). For the structure of a related molecule which does form a hydrogen-bonded dimer in the solid state, see: Vaissermann & Lomas (1997).Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C27H34O | Z = 2 |
Mr = 374.54 | F(000) = 408 |
Triclinic, P1 | Dx = 1.195 Mg m−3 |
Hall symbol: -P 1 | Melting point: 404 K |
a = 6.4065 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.1474 (4) Å | Cell parameters from 4289 reflections |
c = 13.3466 (4) Å | θ = 3.1–27.8° |
α = 70.718 (3)° | µ = 0.07 mm−1 |
β = 81.700 (3)° | T = 120 K |
γ = 80.134 (3)° | Block, colourless |
V = 1040.75 (6) Å3 | 0.50 × 0.50 × 0.40 mm |
Agilent Xcalibur (Sapphire2) diffractometer | 3675 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2925 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.010 |
Detector resolution: 8.4353 pixels mm-1 | θmax = 25.0°, θmin = 3.2° |
ω scan | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −15→15 |
Tmin = 0.996, Tmax = 1.000 | l = −10→15 |
6750 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0483P)2 + 0.1419P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.094 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.18 e Å−3 |
3675 reflections | Δρmin = −0.19 e Å−3 |
258 parameters |
C27H34O | γ = 80.134 (3)° |
Mr = 374.54 | V = 1040.75 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.4065 (2) Å | Mo Kα radiation |
b = 13.1474 (4) Å | µ = 0.07 mm−1 |
c = 13.3466 (4) Å | T = 120 K |
α = 70.718 (3)° | 0.50 × 0.50 × 0.40 mm |
β = 81.700 (3)° |
Agilent Xcalibur (Sapphire2) diffractometer | 3675 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 2925 reflections with I > 2σ(I) |
Tmin = 0.996, Tmax = 1.000 | Rint = 0.010 |
6750 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.18 e Å−3 |
3675 reflections | Δρmin = −0.19 e Å−3 |
258 parameters |
Experimental. Spectral properties of title compound: 1H NMR (500 MHz; CDCl3): δ 1.36 (bs, 1H); 1.71 (m, 6H); 1.82(m, 6H); 2.06 (m, 3H); 2.32(s, 6H); 2.68(d, 2H); 3.02(d, 2H); 6.87(d, 4H); 7.01(d, 4H) p.p.m.. 13C NMR (75.5 MHz; CDCl3): δ 21.2 (CH3); 29.0 (CH); 36.7 (CH2); 37.4 (CH2); 40.0 (CH2); 41.3 (C); 76.7(C); 128.9 (CH); 131.2 (CH); 135.5(C); 135.7(C) p.p.m.. IR (KBr): 3581(s), 2918(s), 2904(s), 2879(s), 2852(s), 1511(m), 1454(m), 1344(m), 1107(w), 1059(w), 1041(w), 997(w), 966(w), 847(w), 818(m), 808(m), 752(m), 714(w), 579(m), 496(w), 476(w) cm-1 MS (EI, 70 eV): 77 (5), 79 (15), 91 (6), 93 (10), 105 (24), 107 (6), 135 (100), 136 (11), 269 (27), 270 (6) m/z(%). |
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. |
x | y | z | Uiso*/Ueq | ||
O2 | 0.52442 (14) | 0.31340 (7) | 0.53822 (7) | 0.0244 (2) | |
H2 | 0.577 (2) | 0.3189 (12) | 0.4778 (12) | 0.037* | |
C1 | 0.3383 (2) | 0.18382 (10) | 0.49612 (10) | 0.0227 (3) | |
H1A | 0.3365 | 0.1115 | 0.5508 | 0.027* | |
H1B | 0.2087 | 0.1990 | 0.4584 | 0.027* | |
C2 | 0.32531 (19) | 0.27081 (9) | 0.55451 (9) | 0.0203 (3) | |
C3 | 0.1531 (2) | 0.36778 (10) | 0.51005 (9) | 0.0246 (3) | |
H3A | 0.0114 | 0.3432 | 0.5345 | 0.030* | |
H3B | 0.1616 | 0.4255 | 0.5411 | 0.030* | |
C11 | 0.5301 (2) | 0.17801 (9) | 0.41677 (10) | 0.0214 (3) | |
C12 | 0.5241 (2) | 0.22950 (10) | 0.30754 (10) | 0.0255 (3) | |
H12 | 0.3955 | 0.2707 | 0.2810 | 0.031* | |
C13 | 0.7026 (2) | 0.22165 (11) | 0.23704 (10) | 0.0276 (3) | |
H13 | 0.6933 | 0.2575 | 0.1630 | 0.033* | |
C14 | 0.8939 (2) | 0.16309 (10) | 0.27152 (10) | 0.0242 (3) | |
C15 | 0.9002 (2) | 0.11175 (10) | 0.38029 (10) | 0.0270 (3) | |
H15 | 1.0291 | 0.0706 | 0.4066 | 0.032* | |
C16 | 0.7225 (2) | 0.11930 (10) | 0.45123 (10) | 0.0268 (3) | |
H16 | 0.7323 | 0.0835 | 0.5253 | 0.032* | |
C17 | 1.0884 (2) | 0.15472 (12) | 0.19488 (11) | 0.0322 (3) | |
H17A | 1.1167 | 0.2278 | 0.1504 | 0.048* | |
H17B | 1.0641 | 0.1135 | 0.1494 | 0.048* | |
H17C | 1.2110 | 0.1174 | 0.2350 | 0.048* | |
C20 | 0.28329 (19) | 0.21981 (9) | 0.67801 (9) | 0.0187 (3) | |
C21 | 0.26153 (19) | 0.30786 (9) | 0.73322 (9) | 0.0204 (3) | |
H21A | 0.3918 | 0.3439 | 0.7139 | 0.025* | |
H21B | 0.1396 | 0.3637 | 0.7077 | 0.025* | |
C22 | 0.22752 (19) | 0.25899 (10) | 0.85462 (9) | 0.0219 (3) | |
H22 | 0.2142 | 0.3179 | 0.8880 | 0.026* | |
C23 | 0.4157 (2) | 0.17335 (10) | 0.89566 (10) | 0.0249 (3) | |
H23A | 0.5484 | 0.2073 | 0.8777 | 0.030* | |
H23B | 0.3933 | 0.1419 | 0.9742 | 0.030* | |
C24 | 0.4346 (2) | 0.08420 (10) | 0.84410 (10) | 0.0233 (3) | |
H24 | 0.5580 | 0.0282 | 0.8704 | 0.028* | |
C25 | 0.2308 (2) | 0.03049 (10) | 0.87323 (10) | 0.0242 (3) | |
H25A | 0.2069 | −0.0018 | 0.9516 | 0.029* | |
H25B | 0.2443 | −0.0283 | 0.8408 | 0.029* | |
C26 | 0.04286 (19) | 0.11655 (10) | 0.83190 (10) | 0.0225 (3) | |
H26 | −0.0908 | 0.0819 | 0.8512 | 0.027* | |
C27 | 0.0222 (2) | 0.20631 (10) | 0.88350 (10) | 0.0237 (3) | |
H27A | −0.0034 | 0.1752 | 0.9619 | 0.028* | |
H27B | −0.1001 | 0.2618 | 0.8578 | 0.028* | |
C28 | 0.47010 (19) | 0.13264 (10) | 0.72260 (10) | 0.0217 (3) | |
H28A | 0.4849 | 0.0740 | 0.6899 | 0.026* | |
H28B | 0.6039 | 0.1657 | 0.7033 | 0.026* | |
C29 | 0.07725 (19) | 0.16575 (10) | 0.71028 (9) | 0.0212 (3) | |
H29A | −0.0458 | 0.2206 | 0.6843 | 0.025* | |
H29B | 0.0873 | 0.1080 | 0.6768 | 0.025* | |
C31 | 0.1692 (2) | 0.41644 (9) | 0.39017 (10) | 0.0224 (3) | |
C32 | 0.0303 (2) | 0.39663 (10) | 0.32966 (10) | 0.0245 (3) | |
H32 | −0.0785 | 0.3528 | 0.3646 | 0.029* | |
C33 | 0.0475 (2) | 0.43953 (10) | 0.21956 (10) | 0.0247 (3) | |
H33 | −0.0503 | 0.4251 | 0.1804 | 0.030* | |
C34 | 0.2054 (2) | 0.50325 (10) | 0.16543 (10) | 0.0243 (3) | |
C35 | 0.3418 (2) | 0.52453 (10) | 0.22592 (10) | 0.0271 (3) | |
H35 | 0.4506 | 0.5684 | 0.1909 | 0.033* | |
C36 | 0.3228 (2) | 0.48324 (10) | 0.33613 (10) | 0.0265 (3) | |
H36 | 0.4160 | 0.5008 | 0.3754 | 0.032* | |
C37 | 0.2247 (2) | 0.55055 (11) | 0.04572 (10) | 0.0321 (3) | |
H37A | 0.3466 | 0.5915 | 0.0223 | 0.048* | |
H37B | 0.0944 | 0.5992 | 0.0230 | 0.048* | |
H37C | 0.2457 | 0.4917 | 0.0140 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0262 (5) | 0.0263 (5) | 0.0211 (5) | −0.0112 (4) | 0.0051 (4) | −0.0072 (4) |
C1 | 0.0260 (7) | 0.0196 (6) | 0.0224 (7) | −0.0041 (5) | −0.0023 (5) | −0.0058 (5) |
C2 | 0.0207 (6) | 0.0182 (6) | 0.0213 (6) | −0.0051 (5) | 0.0002 (5) | −0.0047 (5) |
C3 | 0.0308 (7) | 0.0203 (6) | 0.0199 (6) | −0.0006 (5) | −0.0008 (5) | −0.0047 (5) |
C11 | 0.0252 (7) | 0.0168 (6) | 0.0235 (7) | −0.0021 (5) | −0.0040 (5) | −0.0077 (5) |
C12 | 0.0266 (7) | 0.0263 (7) | 0.0240 (7) | 0.0019 (6) | −0.0073 (6) | −0.0091 (6) |
C13 | 0.0350 (8) | 0.0279 (7) | 0.0191 (7) | −0.0023 (6) | −0.0027 (6) | −0.0070 (5) |
C14 | 0.0268 (7) | 0.0222 (7) | 0.0273 (7) | −0.0042 (5) | −0.0011 (5) | −0.0130 (5) |
C15 | 0.0260 (7) | 0.0252 (7) | 0.0297 (7) | 0.0046 (6) | −0.0074 (6) | −0.0107 (6) |
C16 | 0.0342 (8) | 0.0233 (7) | 0.0200 (7) | 0.0026 (6) | −0.0044 (6) | −0.0051 (5) |
C17 | 0.0304 (8) | 0.0355 (8) | 0.0336 (8) | −0.0048 (6) | 0.0016 (6) | −0.0165 (6) |
C20 | 0.0176 (6) | 0.0175 (6) | 0.0199 (6) | −0.0038 (5) | −0.0005 (5) | −0.0043 (5) |
C21 | 0.0198 (6) | 0.0189 (6) | 0.0217 (6) | −0.0051 (5) | −0.0016 (5) | −0.0042 (5) |
C22 | 0.0235 (7) | 0.0220 (7) | 0.0202 (6) | −0.0049 (5) | −0.0021 (5) | −0.0058 (5) |
C23 | 0.0227 (7) | 0.0290 (7) | 0.0207 (7) | −0.0072 (5) | −0.0041 (5) | −0.0021 (5) |
C24 | 0.0191 (7) | 0.0215 (6) | 0.0247 (7) | −0.0007 (5) | −0.0039 (5) | −0.0012 (5) |
C25 | 0.0249 (7) | 0.0208 (7) | 0.0228 (7) | −0.0056 (5) | −0.0001 (5) | −0.0009 (5) |
C26 | 0.0177 (6) | 0.0227 (7) | 0.0246 (7) | −0.0074 (5) | 0.0006 (5) | −0.0029 (5) |
C27 | 0.0216 (7) | 0.0261 (7) | 0.0195 (6) | −0.0038 (5) | 0.0018 (5) | −0.0031 (5) |
C28 | 0.0172 (6) | 0.0206 (6) | 0.0243 (7) | −0.0037 (5) | 0.0001 (5) | −0.0033 (5) |
C29 | 0.0189 (6) | 0.0203 (6) | 0.0238 (7) | −0.0041 (5) | −0.0031 (5) | −0.0051 (5) |
C31 | 0.0274 (7) | 0.0162 (6) | 0.0222 (7) | 0.0011 (5) | −0.0032 (5) | −0.0061 (5) |
C32 | 0.0227 (7) | 0.0196 (6) | 0.0279 (7) | −0.0007 (5) | −0.0015 (5) | −0.0044 (5) |
C33 | 0.0248 (7) | 0.0242 (7) | 0.0263 (7) | 0.0003 (5) | −0.0078 (5) | −0.0092 (5) |
C34 | 0.0289 (7) | 0.0213 (7) | 0.0214 (7) | 0.0019 (5) | −0.0040 (5) | −0.0068 (5) |
C35 | 0.0314 (8) | 0.0229 (7) | 0.0252 (7) | −0.0074 (6) | −0.0030 (6) | −0.0029 (5) |
C36 | 0.0357 (8) | 0.0211 (7) | 0.0245 (7) | −0.0075 (6) | −0.0077 (6) | −0.0054 (5) |
C37 | 0.0338 (8) | 0.0370 (8) | 0.0233 (7) | −0.0013 (6) | −0.0040 (6) | −0.0077 (6) |
O2—C2 | 1.4395 (14) | C22—H22 | 1.0000 |
O2—H2 | 0.812 (15) | C23—C24 | 1.5239 (18) |
C1—C11 | 1.5109 (17) | C23—H23A | 0.9900 |
C1—C2 | 1.5683 (16) | C23—H23B | 0.9900 |
C1—H1A | 0.9900 | C24—C25 | 1.5303 (16) |
C1—H1B | 0.9900 | C24—C28 | 1.5324 (16) |
C2—C3 | 1.5498 (17) | C24—H24 | 1.0000 |
C2—C20 | 1.5630 (16) | C25—C26 | 1.5320 (17) |
C3—C31 | 1.5096 (16) | C25—H25A | 0.9900 |
C3—H3A | 0.9900 | C25—H25B | 0.9900 |
C3—H3B | 0.9900 | C26—C27 | 1.5301 (17) |
C11—C16 | 1.3894 (17) | C26—C29 | 1.5342 (16) |
C11—C12 | 1.3930 (17) | C26—H26 | 1.0000 |
C12—C13 | 1.3841 (18) | C27—H27A | 0.9900 |
C12—H12 | 0.9500 | C27—H27B | 0.9900 |
C13—C14 | 1.3828 (18) | C28—H28A | 0.9900 |
C13—H13 | 0.9500 | C28—H28B | 0.9900 |
C14—C15 | 1.3875 (18) | C29—H29A | 0.9900 |
C14—C17 | 1.5071 (17) | C29—H29B | 0.9900 |
C15—C16 | 1.3836 (18) | C31—C36 | 1.3900 (17) |
C15—H15 | 0.9500 | C31—C32 | 1.3920 (18) |
C16—H16 | 0.9500 | C32—C33 | 1.3845 (17) |
C17—H17A | 0.9800 | C32—H32 | 0.9500 |
C17—H17B | 0.9800 | C33—C34 | 1.3881 (18) |
C17—H17C | 0.9800 | C33—H33 | 0.9500 |
C20—C21 | 1.5430 (16) | C34—C35 | 1.3891 (18) |
C20—C28 | 1.5444 (17) | C34—C37 | 1.5059 (17) |
C20—C29 | 1.5454 (16) | C35—C36 | 1.3845 (17) |
C21—C22 | 1.5311 (16) | C35—H35 | 0.9500 |
C21—H21A | 0.9900 | C36—H36 | 0.9500 |
C21—H21B | 0.9900 | C37—H37A | 0.9800 |
C22—C23 | 1.5293 (17) | C37—H37B | 0.9800 |
C22—C27 | 1.5325 (17) | C37—H37C | 0.9800 |
C2—O2—H2 | 108.8 (11) | C24—C23—H23B | 109.9 |
C11—C1—C2 | 116.07 (10) | C22—C23—H23B | 109.9 |
C11—C1—H1A | 108.3 | H23A—C23—H23B | 108.3 |
C2—C1—H1A | 108.3 | C23—C24—C25 | 109.95 (10) |
C11—C1—H1B | 108.3 | C23—C24—C28 | 109.94 (10) |
C2—C1—H1B | 108.3 | C25—C24—C28 | 109.14 (10) |
H1A—C1—H1B | 107.4 | C23—C24—H24 | 109.3 |
O2—C2—C3 | 107.41 (9) | C25—C24—H24 | 109.3 |
O2—C2—C20 | 105.06 (9) | C28—C24—H24 | 109.3 |
C3—C2—C20 | 111.35 (10) | C24—C25—C26 | 108.95 (10) |
O2—C2—C1 | 111.17 (9) | C24—C25—H25A | 109.9 |
C3—C2—C1 | 110.22 (10) | C26—C25—H25A | 109.9 |
C20—C2—C1 | 111.46 (9) | C24—C25—H25B | 109.9 |
C31—C3—C2 | 115.30 (10) | C26—C25—H25B | 109.9 |
C31—C3—H3A | 108.4 | H25A—C25—H25B | 108.3 |
C2—C3—H3A | 108.4 | C27—C26—C25 | 109.41 (10) |
C31—C3—H3B | 108.4 | C27—C26—C29 | 109.57 (10) |
C2—C3—H3B | 108.4 | C25—C26—C29 | 110.20 (10) |
H3A—C3—H3B | 107.5 | C27—C26—H26 | 109.2 |
C16—C11—C12 | 117.03 (11) | C25—C26—H26 | 109.2 |
C16—C11—C1 | 120.32 (11) | C29—C26—H26 | 109.2 |
C12—C11—C1 | 122.66 (11) | C26—C27—C22 | 109.25 (10) |
C13—C12—C11 | 121.09 (12) | C26—C27—H27A | 109.8 |
C13—C12—H12 | 119.5 | C22—C27—H27A | 109.8 |
C11—C12—H12 | 119.5 | C26—C27—H27B | 109.8 |
C14—C13—C12 | 121.78 (12) | C22—C27—H27B | 109.8 |
C14—C13—H13 | 119.1 | H27A—C27—H27B | 108.3 |
C12—C13—H13 | 119.1 | C24—C28—C20 | 111.27 (10) |
C13—C14—C15 | 117.24 (12) | C24—C28—H28A | 109.4 |
C13—C14—C17 | 121.84 (12) | C20—C28—H28A | 109.4 |
C15—C14—C17 | 120.92 (12) | C24—C28—H28B | 109.4 |
C16—C15—C14 | 121.29 (12) | C20—C28—H28B | 109.4 |
C16—C15—H15 | 119.4 | H28A—C28—H28B | 108.0 |
C14—C15—H15 | 119.4 | C26—C29—C20 | 110.41 (10) |
C15—C16—C11 | 121.57 (12) | C26—C29—H29A | 109.6 |
C15—C16—H16 | 119.2 | C20—C29—H29A | 109.6 |
C11—C16—H16 | 119.2 | C26—C29—H29B | 109.6 |
C14—C17—H17A | 109.5 | C20—C29—H29B | 109.6 |
C14—C17—H17B | 109.5 | H29A—C29—H29B | 108.1 |
H17A—C17—H17B | 109.5 | C36—C31—C32 | 117.51 (11) |
C14—C17—H17C | 109.5 | C36—C31—C3 | 121.18 (11) |
H17A—C17—H17C | 109.5 | C32—C31—C3 | 121.31 (11) |
H17B—C17—H17C | 109.5 | C33—C32—C31 | 121.35 (12) |
C21—C20—C28 | 107.74 (10) | C33—C32—H32 | 119.3 |
C21—C20—C29 | 107.66 (10) | C31—C32—H32 | 119.3 |
C28—C20—C29 | 107.99 (9) | C32—C33—C34 | 121.08 (12) |
C21—C20—C2 | 110.48 (9) | C32—C33—H33 | 119.5 |
C28—C20—C2 | 110.59 (9) | C34—C33—H33 | 119.5 |
C29—C20—C2 | 112.22 (9) | C33—C34—C35 | 117.56 (11) |
C22—C21—C20 | 111.34 (9) | C33—C34—C37 | 121.41 (12) |
C22—C21—H21A | 109.4 | C35—C34—C37 | 121.00 (12) |
C20—C21—H21A | 109.4 | C36—C35—C34 | 121.48 (12) |
C22—C21—H21B | 109.4 | C36—C35—H35 | 119.3 |
C20—C21—H21B | 109.4 | C34—C35—H35 | 119.3 |
H21A—C21—H21B | 108.0 | C35—C36—C31 | 120.96 (12) |
C23—C22—C21 | 110.08 (10) | C35—C36—H36 | 119.5 |
C23—C22—C27 | 109.69 (10) | C31—C36—H36 | 119.5 |
C21—C22—C27 | 108.76 (10) | C34—C37—H37A | 109.5 |
C23—C22—H22 | 109.4 | C34—C37—H37B | 109.5 |
C21—C22—H22 | 109.4 | H37A—C37—H37B | 109.5 |
C27—C22—H22 | 109.4 | C34—C37—H37C | 109.5 |
C24—C23—C22 | 108.95 (10) | H37A—C37—H37C | 109.5 |
C24—C23—H23A | 109.9 | H37B—C37—H37C | 109.5 |
C22—C23—H23A | 109.9 | ||
C11—C1—C2—O2 | −12.69 (14) | C27—C22—C23—C24 | 60.05 (13) |
C11—C1—C2—C3 | 106.29 (12) | C22—C23—C24—C25 | −60.43 (12) |
C11—C1—C2—C20 | −129.54 (11) | C22—C23—C24—C28 | 59.76 (13) |
O2—C2—C3—C31 | 70.51 (13) | C23—C24—C25—C26 | 60.58 (13) |
C20—C2—C3—C31 | −174.97 (10) | C28—C24—C25—C26 | −60.10 (13) |
C1—C2—C3—C31 | −50.74 (14) | C24—C25—C26—C27 | −60.16 (12) |
C2—C1—C11—C16 | 82.61 (14) | C24—C25—C26—C29 | 60.37 (13) |
C2—C1—C11—C12 | −97.68 (14) | C25—C26—C27—C22 | 60.14 (12) |
C16—C11—C12—C13 | 0.28 (18) | C29—C26—C27—C22 | −60.78 (13) |
C1—C11—C12—C13 | −179.44 (12) | C23—C22—C27—C26 | −60.16 (13) |
C11—C12—C13—C14 | −0.2 (2) | C21—C22—C27—C26 | 60.29 (12) |
C12—C13—C14—C15 | 0.21 (19) | C23—C24—C28—C20 | −60.11 (13) |
C12—C13—C14—C17 | −179.83 (12) | C25—C24—C28—C20 | 60.57 (13) |
C13—C14—C15—C16 | −0.25 (19) | C21—C20—C28—C24 | 57.46 (12) |
C17—C14—C15—C16 | 179.79 (12) | C29—C20—C28—C24 | −58.57 (13) |
C14—C15—C16—C11 | 0.3 (2) | C2—C20—C28—C24 | 178.29 (9) |
C12—C11—C16—C15 | −0.32 (18) | C27—C26—C29—C20 | 60.53 (13) |
C1—C11—C16—C15 | 179.40 (12) | C25—C26—C29—C20 | −59.90 (13) |
O2—C2—C20—C21 | 61.95 (12) | C21—C20—C29—C26 | −58.42 (12) |
C3—C2—C20—C21 | −54.02 (13) | C28—C20—C29—C26 | 57.66 (13) |
C1—C2—C20—C21 | −177.55 (10) | C2—C20—C29—C26 | 179.80 (9) |
O2—C2—C20—C28 | −57.24 (12) | C2—C3—C31—C36 | −75.74 (15) |
C3—C2—C20—C28 | −173.21 (10) | C2—C3—C31—C32 | 104.61 (14) |
C1—C2—C20—C28 | 63.26 (12) | C36—C31—C32—C33 | 1.60 (18) |
O2—C2—C20—C29 | −177.90 (9) | C3—C31—C32—C33 | −178.75 (11) |
C3—C2—C20—C29 | 66.14 (13) | C31—C32—C33—C34 | 0.53 (19) |
C1—C2—C20—C29 | −57.40 (13) | C32—C33—C34—C35 | −1.57 (19) |
C28—C20—C21—C22 | −57.24 (12) | C32—C33—C34—C37 | −179.77 (12) |
C29—C20—C21—C22 | 59.00 (12) | C33—C34—C35—C36 | 0.49 (19) |
C2—C20—C21—C22 | −178.14 (9) | C37—C34—C35—C36 | 178.69 (12) |
C20—C21—C22—C23 | 59.62 (13) | C34—C35—C36—C31 | 1.7 (2) |
C20—C21—C22—C27 | −60.58 (13) | C32—C31—C36—C35 | −2.67 (18) |
C21—C22—C23—C24 | −59.59 (12) | C3—C31—C36—C35 | 177.67 (11) |
Cg1 is the centroid of the C31–C36 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···Cg1 | 0.94 | 2.61 | 3.3577 (12) | 136 |
Experimental details
Crystal data | |
Chemical formula | C27H34O |
Mr | 374.54 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 120 |
a, b, c (Å) | 6.4065 (2), 13.1474 (4), 13.3466 (4) |
α, β, γ (°) | 70.718 (3), 81.700 (3), 80.134 (3) |
V (Å3) | 1040.75 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.50 × 0.50 × 0.40 |
Data collection | |
Diffractometer | Agilent Xcalibur (Sapphire2) |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011) |
Tmin, Tmax | 0.996, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6750, 3675, 2925 |
Rint | 0.010 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.094, 1.07 |
No. of reflections | 3675 |
No. of parameters | 258 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.18, −0.19 |
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008).
Cg1 is the centroid of the C31–C36 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···Cg1 | 0.94 | 2.61 | 3.3577 (12) | 135.5 |
Acknowledgements
The financial support of this work by the Internal Founding Agency of Tomas Bata University in Zlin (project No. IGA/FT/2012/016) is gratefully acknowledged.
References
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The title molecule consists of two p-methylated benzene rings, the adamantane cage and propane-2-ol backbone to form a strained tertiary alcohol (Fig. 1). Both benzene rings are essentially planar with maximum deviations from their least squares best planes of 0.0013 (14) Å for C16 and 0.0138 (14) Å for C36, respectively. The dihedral angle between these best planes is 54.79 (4)°. The torsion angles C20—C2—C3—C31, C20—C2—C1—C11, C2—C1—C11—C12, C2—C3—C31—C32 and C21—C20—C2—O2 are -174.97 (10), -129.54 (11), -97.69 (15), 104.62 (14) and 61.95 (12)°, respectively. The conformation of the molecules in the solid state is stabilized by a weak C—H···π interaction, C12—H12···Cg1 (Cg1 is the centre of gravity of C31–C36), with a C12–Cg1 distance of 3.3576 (12) Å (Fig. 2, Table 1). In contrast to the more strained molecules of di(1-adamantyl)(2,5-diisopropylphenyl)methanol those form H-bonded dimers in the solid state (Vaissermann & Lomas, 1997), no H-bonds were observed in the crystal packing of the title compound. The shortest distance between two adjacent O-atoms is 4.6340 (13) Å (Fig. 2). Some other examples of such sterically shielded carbinols have been previously published (Babjaková et al., 2010; Vícha & Nečas, 2010).