The structure of 4-cumylphenol, C15H16O, exhibits chains of hydrogen-bonded molecules along the c axis.
Supporting information
CCDC reference: 242308
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.049
- wR factor = 0.128
- Data-to-parameter ratio = 19.4
checkCIF/PLATON results
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1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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Data collection: COLLECT (Nonius BV, 1999); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
4-(2-phenylisopropyl)phenol
top
Crystal data top
C15H16O | Dx = 1.174 Mg m−3 |
Mr = 212.28 | Mo Kα radiation, λ = 0.71069 Å |
Hexagonal, R3 | Cell parameters from 8097 reflections |
a = 30.989 (4) Å | θ = 1.0–27.9° |
c = 6.500 (1) Å | µ = 0.07 mm−1 |
V = 5405.5 (13) Å3 | T = 150 K |
Z = 18 | Prism, colorless |
F(000) = 2052 | 0.40 × 0.15 × 0.15 mm |
Data collection top
KappaCCD diffractometer | 1948 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Horizonally mounted graphite crystal monochromator | θmax = 27.9°, θmin = 3.5° |
Detector resolution: 9 pixels mm-1 | h = −40→19 |
CCD scans | k = 0→40 |
2855 measured reflections | l = 0→8 |
2855 independent 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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0636P)2 + 5.893P] where P = (Fo2 + 2Fc2)/3 |
2855 reflections | (Δ/σ)max = 0.004 |
147 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Special details top
Experimental. Diffractometer equiped with an area detector. phi scans and omega scans during
20 s with 2 ° steps Crystal to detector distance: 30 mm |
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 | Uiso*/Ueq | |
O1 | 0.34804 (4) | 0.03489 (4) | 0.01722 (16) | 0.0336 (3) | |
H1 | 0.3351 | 0.0193 | −0.0902 | 0.050* | |
C1 | 0.36952 (5) | 0.08549 (6) | −0.0195 (2) | 0.0268 (3) | |
C2 | 0.39345 (6) | 0.11810 (6) | 0.1415 (2) | 0.0287 (4) | |
H2 | 0.3958 | 0.1059 | 0.2708 | 0.034* | |
C3 | 0.41382 (6) | 0.16878 (6) | 0.1110 (2) | 0.0283 (4) | |
H3 | 0.4296 | 0.1906 | 0.2218 | 0.034* | |
C4 | 0.41168 (5) | 0.18850 (6) | −0.0795 (2) | 0.0268 (3) | |
C5 | 0.38846 (6) | 0.15488 (6) | −0.2388 (2) | 0.0311 (4) | |
H5 | 0.3868 | 0.1670 | −0.3696 | 0.037* | |
C6 | 0.36758 (6) | 0.10389 (6) | −0.2103 (2) | 0.0316 (4) | |
H6 | 0.3521 | 0.0819 | −0.3210 | 0.038* | |
C7 | 0.43124 (6) | 0.24464 (6) | −0.1009 (2) | 0.0290 (4) | |
C8 | 0.48275 (6) | 0.27424 (6) | −0.0007 (2) | 0.0261 (3) | |
C9 | 0.52031 (6) | 0.26461 (6) | −0.0604 (2) | 0.0281 (3) | |
H9 | 0.5130 | 0.2388 | −0.1547 | 0.034* | |
C10 | 0.56813 (6) | 0.29222 (6) | 0.0165 (2) | 0.0312 (4) | |
H10 | 0.5930 | 0.2852 | −0.0262 | 0.037* | |
C11 | 0.57953 (6) | 0.33019 (6) | 0.1564 (2) | 0.0338 (4) | |
H11 | 0.6122 | 0.3494 | 0.2067 | 0.041* | |
C12 | 0.54276 (7) | 0.33956 (6) | 0.2211 (2) | 0.0363 (4) | |
H12 | 0.5501 | 0.3647 | 0.3185 | 0.044* | |
C13 | 0.49467 (7) | 0.31187 (6) | 0.1426 (2) | 0.0338 (4) | |
H13 | 0.4699 | 0.3187 | 0.1873 | 0.041* | |
C14 | 0.43700 (7) | 0.26118 (6) | −0.3281 (2) | 0.0365 (4) | |
H14A | 0.4046 | 0.2446 | −0.3946 | 0.055* | |
H14B | 0.4592 | 0.2523 | −0.3978 | 0.055* | |
H14C | 0.4508 | 0.2970 | −0.3347 | 0.055* | |
C15 | 0.39263 (7) | 0.25528 (7) | 0.0002 (3) | 0.0393 (4) | |
H15A | 0.3910 | 0.2485 | 0.1465 | 0.059* | |
H15B | 0.3602 | 0.2341 | −0.0612 | 0.059* | |
H15C | 0.4023 | 0.2900 | −0.0210 | 0.059* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0369 (7) | 0.0304 (6) | 0.0304 (6) | 0.0145 (5) | −0.0064 (5) | 0.0001 (5) |
C1 | 0.0223 (8) | 0.0298 (8) | 0.0289 (7) | 0.0136 (7) | −0.0001 (6) | 0.0020 (6) |
C2 | 0.0265 (8) | 0.0365 (9) | 0.0222 (7) | 0.0150 (7) | −0.0014 (6) | 0.0046 (6) |
C3 | 0.0253 (8) | 0.0332 (9) | 0.0229 (7) | 0.0121 (7) | −0.0019 (6) | −0.0011 (6) |
C4 | 0.0226 (8) | 0.0327 (9) | 0.0260 (7) | 0.0144 (7) | 0.0013 (6) | 0.0019 (6) |
C5 | 0.0357 (9) | 0.0363 (9) | 0.0226 (7) | 0.0189 (8) | −0.0029 (6) | 0.0027 (6) |
C6 | 0.0340 (9) | 0.0358 (9) | 0.0247 (8) | 0.0172 (8) | −0.0080 (6) | −0.0041 (6) |
C7 | 0.0315 (9) | 0.0320 (9) | 0.0264 (8) | 0.0181 (7) | −0.0003 (6) | 0.0016 (6) |
C8 | 0.0308 (8) | 0.0254 (8) | 0.0228 (7) | 0.0146 (7) | 0.0023 (6) | 0.0034 (6) |
C9 | 0.0319 (8) | 0.0262 (8) | 0.0242 (7) | 0.0131 (7) | 0.0009 (6) | −0.0012 (6) |
C10 | 0.0299 (9) | 0.0329 (9) | 0.0292 (8) | 0.0146 (7) | 0.0032 (6) | 0.0036 (6) |
C11 | 0.0350 (9) | 0.0278 (9) | 0.0305 (8) | 0.0096 (7) | −0.0051 (7) | 0.0022 (7) |
C12 | 0.0498 (11) | 0.0274 (9) | 0.0297 (8) | 0.0178 (8) | −0.0053 (7) | −0.0048 (7) |
C13 | 0.0435 (10) | 0.0348 (9) | 0.0293 (8) | 0.0242 (8) | 0.0017 (7) | −0.0015 (7) |
C14 | 0.0414 (10) | 0.0368 (10) | 0.0313 (9) | 0.0196 (8) | −0.0032 (7) | 0.0055 (7) |
C15 | 0.0364 (10) | 0.0468 (11) | 0.0431 (10) | 0.0271 (9) | 0.0009 (7) | 0.0010 (8) |
Geometric parameters (Å, º) top
O1—C1 | 1.3838 (18) | C8—C9 | 1.394 (2) |
O1—H1 | 0.8300 | C9—C10 | 1.382 (2) |
C1—C6 | 1.379 (2) | C9—H9 | 0.9400 |
C1—C2 | 1.385 (2) | C10—C11 | 1.386 (2) |
C2—C3 | 1.383 (2) | C10—H10 | 0.9400 |
C2—H2 | 0.9400 | C11—C12 | 1.375 (2) |
C3—C4 | 1.397 (2) | C11—H11 | 0.9400 |
C3—H3 | 0.9400 | C12—C13 | 1.392 (2) |
C4—C5 | 1.388 (2) | C12—H12 | 0.9400 |
C4—C7 | 1.536 (2) | C13—H13 | 0.9400 |
C5—C6 | 1.388 (2) | C14—H14A | 0.9700 |
C5—H5 | 0.9400 | C14—H14B | 0.9700 |
C6—H6 | 0.9400 | C14—H14C | 0.9700 |
C7—C8 | 1.533 (2) | C15—H15A | 0.9700 |
C7—C15 | 1.538 (2) | C15—H15B | 0.9700 |
C7—C14 | 1.544 (2) | C15—H15C | 0.9700 |
C8—C13 | 1.390 (2) | | |
| | | |
C1—O1—H1 | 109.5 | C10—C9—C8 | 121.25 (14) |
C6—C1—O1 | 121.89 (14) | C10—C9—H9 | 119.4 |
C6—C1—C2 | 119.75 (15) | C8—C9—H9 | 119.4 |
O1—C1—C2 | 118.36 (13) | C9—C10—C11 | 120.13 (15) |
C3—C2—C1 | 119.62 (13) | C9—C10—H10 | 119.9 |
C3—C2—H2 | 120.2 | C11—C10—H10 | 119.9 |
C1—C2—H2 | 120.2 | C12—C11—C10 | 119.59 (15) |
C2—C3—C4 | 121.95 (14) | C12—C11—H11 | 120.2 |
C2—C3—H3 | 119.0 | C10—C11—H11 | 120.2 |
C4—C3—H3 | 119.0 | C11—C12—C13 | 120.16 (15) |
C5—C4—C3 | 116.94 (14) | C11—C12—H12 | 119.9 |
C5—C4—C7 | 123.08 (13) | C13—C12—H12 | 119.9 |
C3—C4—C7 | 119.83 (13) | C8—C13—C12 | 121.06 (15) |
C4—C5—C6 | 121.78 (13) | C8—C13—H13 | 119.5 |
C4—C5—H5 | 119.1 | C12—C13—H13 | 119.5 |
C6—C5—H5 | 119.1 | C7—C14—H14A | 109.5 |
C1—C6—C5 | 119.92 (14) | C7—C14—H14B | 109.5 |
C1—C6—H6 | 120.0 | H14A—C14—H14B | 109.5 |
C5—C6—H6 | 120.0 | C7—C14—H14C | 109.5 |
C8—C7—C4 | 110.03 (12) | H14A—C14—H14C | 109.5 |
C8—C7—C15 | 112.26 (13) | H14B—C14—H14C | 109.5 |
C4—C7—C15 | 107.18 (13) | C7—C15—H15A | 109.5 |
C8—C7—C14 | 107.16 (13) | C7—C15—H15B | 109.5 |
C4—C7—C14 | 112.16 (13) | H15A—C15—H15B | 109.5 |
C15—C7—C14 | 108.10 (13) | C7—C15—H15C | 109.5 |
C13—C8—C9 | 117.78 (15) | H15A—C15—H15C | 109.5 |
C13—C8—C7 | 123.17 (14) | H15B—C15—H15C | 109.5 |
C9—C8—C7 | 119.00 (13) | | |
| | | |
C6—C1—C2—C3 | 2.0 (2) | C3—C4—C7—C14 | 166.89 (14) |
O1—C1—C2—C3 | −177.87 (13) | C4—C7—C8—C13 | −128.63 (15) |
C1—C2—C3—C4 | −0.9 (2) | C15—C7—C8—C13 | −9.4 (2) |
C2—C3—C4—C5 | −0.6 (2) | C14—C7—C8—C13 | 109.18 (16) |
C2—C3—C4—C7 | 175.24 (14) | C4—C7—C8—C9 | 53.86 (17) |
C3—C4—C5—C6 | 1.0 (2) | C15—C7—C8—C9 | 173.13 (14) |
C7—C4—C5—C6 | −174.70 (15) | C14—C7—C8—C9 | −68.33 (17) |
O1—C1—C6—C5 | 178.25 (14) | C13—C8—C9—C10 | −1.4 (2) |
C2—C1—C6—C5 | −1.7 (2) | C7—C8—C9—C10 | 176.21 (14) |
C4—C5—C6—C1 | 0.1 (2) | C8—C9—C10—C11 | 0.3 (2) |
C5—C4—C7—C8 | −136.75 (15) | C9—C10—C11—C12 | 1.2 (2) |
C3—C4—C7—C8 | 47.71 (18) | C10—C11—C12—C13 | −1.6 (2) |
C5—C4—C7—C15 | 100.92 (17) | C9—C8—C13—C12 | 1.1 (2) |
C3—C4—C7—C15 | −74.61 (17) | C7—C8—C13—C12 | −176.45 (14) |
C5—C4—C7—C14 | −17.6 (2) | C11—C12—C13—C8 | 0.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O1i | 0.83 | 1.88 | 2.710 (1) | 173 |
Symmetry code: (i) −y+1/3, x−y−1/3, z−1/3. |