Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046120/sj2360sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046120/sj2360Isup2.hkl |
CCDC reference: 672798
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (C-C) = 0.003 Å
- R factor = 0.058
- wR factor = 0.130
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For a related structure, see Wang et al. (2006); for uses of phenol derivatives, see Eidenschink et al. (1978).
For related literature, see: Hu et al. (2003).
The title compound was prepared according to the procedure of Hu et al. (2003). Suitable crystals of (I) were obtained by slow evaporation of a methanol solution.
To avoid an unreasonable intermolecular H···H contact, the H atom of the OH group must be disordered over two positions with equal occupancy so as to form alternative O—H···O bonds to adjacent OH groups. The H atoms of the disordered O—H groups were refined freely with fixed isotropic displacement parameters, Uiso = 1.5Ueq (O). Other H atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.95 Å, Uiso=1.2Ueq (C) for aromatic 1.00 Å, Uiso = 1.2Ueq (C) for CH, 0.99 Å, Uiso = 1.2Ueq (C) for CH2 and 0.98 Å, Uiso = 1.5Ueq (C) for CH3 atoms.
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).
Fig. 1. A view of the molecule of (I), shown with 30% displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii. Only one of the disordered H atoms attached to O1 is shown. |
C15H22O | F(000) = 960 |
Mr = 218.33 | Dx = 1.157 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -C 2yc | Cell parameters from 1756 reflections |
a = 35.062 (5) Å | θ = 3.1–25.0° |
b = 5.3648 (6) Å | µ = 0.07 mm−1 |
c = 13.488 (2) Å | T = 113 K |
β = 98.994 (6)° | Prism, colorless |
V = 2505.9 (6) Å3 | 0.20 × 0.14 × 0.10 mm |
Z = 8 |
Rigaku Saturn CCD diffractometer | 2182 independent reflections |
Radiation source: Rotating anode | 1824 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.053 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.0°, θmin = 2.4° |
ω scans | h = −41→41 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | k = −6→6 |
Tmin = 0.986, Tmax = 0.993 | l = −15→16 |
8805 measured reflections |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0528P)2 + 1.3717P] where P = (Fo2 + 2Fc2)/3 |
2182 reflections | (Δ/σ)max < 0.001 |
153 parameters | Δρmax = 0.18 e Å−3 |
2 restraints | Δρmin = −0.19 e Å−3 |
C15H22O | V = 2505.9 (6) Å3 |
Mr = 218.33 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 35.062 (5) Å | µ = 0.07 mm−1 |
b = 5.3648 (6) Å | T = 113 K |
c = 13.488 (2) Å | 0.20 × 0.14 × 0.10 mm |
β = 98.994 (6)° |
Rigaku Saturn CCD diffractometer | 2182 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | 1824 reflections with I > 2σ(I) |
Tmin = 0.986, Tmax = 0.993 | Rint = 0.053 |
8805 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 2 restraints |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | Δρmax = 0.18 e Å−3 |
2182 reflections | Δρmin = −0.19 e Å−3 |
153 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.24200 (4) | 0.0013 (2) | 0.52977 (10) | 0.0218 (4) | |
H1A | 0.2474 (13) | −0.144 (3) | 0.519 (3) | 0.033* | 0.50 |
H1B | 0.2432 (13) | 0.143 (4) | 0.508 (3) | 0.033* | 0.50 |
C1 | 0.21933 (5) | 0.0111 (3) | 0.60602 (13) | 0.0159 (4) | |
C2 | 0.19413 (5) | 0.2098 (3) | 0.60899 (13) | 0.0176 (4) | |
H2 | 0.1922 | 0.3367 | 0.5593 | 0.021* | |
C3 | 0.17169 (5) | 0.2212 (3) | 0.68538 (13) | 0.0167 (4) | |
H3 | 0.1546 | 0.3580 | 0.6875 | 0.020* | |
C4 | 0.17364 (5) | 0.0360 (3) | 0.75906 (13) | 0.0162 (4) | |
C5 | 0.19938 (5) | −0.1608 (3) | 0.75345 (13) | 0.0168 (4) | |
H5 | 0.2013 | −0.2891 | 0.8025 | 0.020* | |
C6 | 0.22232 (5) | −0.1743 (3) | 0.67816 (13) | 0.0175 (4) | |
H6 | 0.2398 | −0.3090 | 0.6763 | 0.021* | |
C7 | 0.14826 (5) | 0.0456 (3) | 0.84070 (13) | 0.0164 (4) | |
H7 | 0.1574 | −0.0876 | 0.8907 | 0.020* | |
C8 | 0.15084 (5) | 0.2951 (4) | 0.89706 (14) | 0.0192 (4) | |
H8A | 0.1780 | 0.3258 | 0.9274 | 0.023* | |
H8B | 0.1428 | 0.4312 | 0.8487 | 0.023* | |
C9 | 0.12539 (5) | 0.2995 (4) | 0.97970 (13) | 0.0183 (4) | |
H9A | 0.1271 | 0.4661 | 1.0116 | 0.022* | |
H9B | 0.1352 | 0.1755 | 1.0319 | 0.022* | |
C10 | 0.08291 (5) | 0.2411 (3) | 0.93881 (14) | 0.0171 (4) | |
H10 | 0.0729 | 0.3761 | 0.8906 | 0.021* | |
C11 | 0.08033 (5) | −0.0057 (4) | 0.88091 (14) | 0.0216 (5) | |
H11A | 0.0883 | −0.1434 | 0.9285 | 0.026* | |
H11B | 0.0531 | −0.0351 | 0.8504 | 0.026* | |
C12 | 0.10566 (5) | −0.0096 (4) | 0.79842 (14) | 0.0191 (4) | |
H12A | 0.0961 | 0.1165 | 0.7469 | 0.023* | |
H12B | 0.1038 | −0.1753 | 0.7657 | 0.023* | |
C13 | 0.05754 (5) | 0.2345 (4) | 1.02191 (14) | 0.0202 (5) | |
H13A | 0.0310 | 0.1859 | 0.9916 | 0.024* | |
H13B | 0.0676 | 0.1035 | 1.0709 | 0.024* | |
C14 | 0.05541 (6) | 0.4796 (4) | 1.07852 (15) | 0.0245 (5) | |
H14A | 0.0816 | 0.5235 | 1.1129 | 0.029* | |
H14B | 0.0468 | 0.6135 | 1.0296 | 0.029* | |
C15 | 0.02804 (6) | 0.4687 (4) | 1.15591 (15) | 0.0279 (5) | |
H15A | 0.0279 | 0.6304 | 1.1897 | 0.042* | |
H15B | 0.0367 | 0.3392 | 1.2056 | 0.042* | |
H15C | 0.0019 | 0.4294 | 1.1222 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0242 (7) | 0.0202 (8) | 0.0233 (8) | 0.0003 (7) | 0.0111 (6) | −0.0012 (7) |
C1 | 0.0154 (9) | 0.0173 (11) | 0.0155 (9) | −0.0038 (7) | 0.0040 (7) | −0.0047 (8) |
C2 | 0.0186 (9) | 0.0172 (11) | 0.0168 (10) | −0.0011 (8) | 0.0021 (8) | 0.0012 (8) |
C3 | 0.0176 (9) | 0.0129 (10) | 0.0194 (10) | 0.0013 (7) | 0.0025 (8) | −0.0019 (8) |
C4 | 0.0156 (9) | 0.0167 (11) | 0.0157 (9) | −0.0041 (7) | 0.0010 (7) | −0.0025 (8) |
C5 | 0.0197 (9) | 0.0145 (10) | 0.0159 (9) | −0.0009 (8) | 0.0014 (8) | 0.0011 (8) |
C6 | 0.0164 (9) | 0.0142 (10) | 0.0219 (10) | 0.0018 (7) | 0.0032 (8) | −0.0002 (8) |
C7 | 0.0193 (9) | 0.0156 (10) | 0.0146 (9) | 0.0011 (8) | 0.0035 (7) | 0.0001 (8) |
C8 | 0.0169 (9) | 0.0200 (11) | 0.0213 (10) | −0.0022 (8) | 0.0044 (8) | −0.0030 (8) |
C9 | 0.0168 (9) | 0.0213 (11) | 0.0169 (10) | −0.0003 (8) | 0.0033 (7) | −0.0035 (8) |
C10 | 0.0166 (9) | 0.0179 (11) | 0.0174 (10) | −0.0003 (8) | 0.0043 (8) | 0.0004 (8) |
C11 | 0.0195 (9) | 0.0232 (12) | 0.0229 (10) | −0.0063 (8) | 0.0061 (8) | −0.0036 (9) |
C12 | 0.0189 (10) | 0.0175 (11) | 0.0212 (10) | −0.0029 (8) | 0.0038 (8) | −0.0040 (8) |
C13 | 0.0188 (10) | 0.0225 (11) | 0.0198 (10) | −0.0019 (8) | 0.0046 (8) | 0.0013 (9) |
C14 | 0.0235 (10) | 0.0279 (12) | 0.0232 (10) | −0.0017 (9) | 0.0074 (8) | −0.0030 (9) |
C15 | 0.0240 (11) | 0.0379 (14) | 0.0231 (11) | 0.0047 (9) | 0.0077 (9) | −0.0009 (10) |
O1—C1 | 1.396 (2) | C9—C10 | 1.537 (2) |
O1—H1A | 0.817 (10) | C9—H9A | 0.9900 |
O1—H1B | 0.821 (10) | C9—H9B | 0.9900 |
C1—C6 | 1.384 (2) | C10—C11 | 1.533 (2) |
C1—C2 | 1.389 (2) | C10—C13 | 1.536 (2) |
C2—C3 | 1.392 (2) | C10—H10 | 1.0000 |
C2—H2 | 0.9500 | C11—C12 | 1.528 (2) |
C3—C4 | 1.399 (2) | C11—H11A | 0.9900 |
C3—H3 | 0.9500 | C11—H11B | 0.9900 |
C4—C5 | 1.399 (2) | C12—H12A | 0.9900 |
C4—C7 | 1.521 (2) | C12—H12B | 0.9900 |
C5—C6 | 1.393 (2) | C13—C14 | 1.528 (3) |
C5—H5 | 0.9500 | C13—H13A | 0.9900 |
C6—H6 | 0.9500 | C13—H13B | 0.9900 |
C7—C8 | 1.535 (2) | C14—C15 | 1.526 (2) |
C7—C12 | 1.542 (2) | C14—H14A | 0.9900 |
C7—H7 | 1.0000 | C14—H14B | 0.9900 |
C8—C9 | 1.533 (2) | C15—H15A | 0.9800 |
C8—H8A | 0.9900 | C15—H15B | 0.9800 |
C8—H8B | 0.9900 | C15—H15C | 0.9800 |
C1—O1—H1A | 110 (3) | H9A—C9—H9B | 107.9 |
C1—O1—H1B | 107 (3) | C11—C10—C13 | 110.92 (15) |
H1A—O1—H1B | 143 (5) | C11—C10—C9 | 109.61 (15) |
C6—C1—C2 | 120.65 (16) | C13—C10—C9 | 112.45 (15) |
C6—C1—O1 | 120.11 (16) | C11—C10—H10 | 107.9 |
C2—C1—O1 | 119.23 (16) | C13—C10—H10 | 107.9 |
C1—C2—C3 | 119.38 (17) | C9—C10—H10 | 107.9 |
C1—C2—H2 | 120.3 | C12—C11—C10 | 112.82 (15) |
C3—C2—H2 | 120.3 | C12—C11—H11A | 109.0 |
C2—C3—C4 | 121.60 (17) | C10—C11—H11A | 109.0 |
C2—C3—H3 | 119.2 | C12—C11—H11B | 109.0 |
C4—C3—H3 | 119.2 | C10—C11—H11B | 109.0 |
C5—C4—C3 | 117.25 (16) | H11A—C11—H11B | 107.8 |
C5—C4—C7 | 121.34 (16) | C11—C12—C7 | 111.58 (15) |
C3—C4—C7 | 121.39 (16) | C11—C12—H12A | 109.3 |
C6—C5—C4 | 122.00 (17) | C7—C12—H12A | 109.3 |
C6—C5—H5 | 119.0 | C11—C12—H12B | 109.3 |
C4—C5—H5 | 119.0 | C7—C12—H12B | 109.3 |
C1—C6—C5 | 119.11 (17) | H12A—C12—H12B | 108.0 |
C1—C6—H6 | 120.4 | C14—C13—C10 | 115.06 (15) |
C5—C6—H6 | 120.4 | C14—C13—H13A | 108.5 |
C4—C7—C8 | 113.09 (15) | C10—C13—H13A | 108.5 |
C4—C7—C12 | 111.62 (14) | C14—C13—H13B | 108.5 |
C8—C7—C12 | 109.21 (14) | C10—C13—H13B | 108.5 |
C4—C7—H7 | 107.6 | H13A—C13—H13B | 107.5 |
C8—C7—H7 | 107.6 | C15—C14—C13 | 113.18 (16) |
C12—C7—H7 | 107.6 | C15—C14—H14A | 108.9 |
C9—C8—C7 | 112.19 (15) | C13—C14—H14A | 108.9 |
C9—C8—H8A | 109.2 | C15—C14—H14B | 108.9 |
C7—C8—H8A | 109.2 | C13—C14—H14B | 108.9 |
C9—C8—H8B | 109.2 | H14A—C14—H14B | 107.8 |
C7—C8—H8B | 109.2 | C14—C15—H15A | 109.5 |
H8A—C8—H8B | 107.9 | C14—C15—H15B | 109.5 |
C8—C9—C10 | 112.17 (15) | H15A—C15—H15B | 109.5 |
C8—C9—H9A | 109.2 | C14—C15—H15C | 109.5 |
C10—C9—H9A | 109.2 | H15A—C15—H15C | 109.5 |
C8—C9—H9B | 109.2 | H15B—C15—H15C | 109.5 |
C10—C9—H9B | 109.2 | ||
C6—C1—C2—C3 | −0.1 (3) | C4—C7—C8—C9 | −179.37 (14) |
O1—C1—C2—C3 | −179.52 (16) | C12—C7—C8—C9 | 55.69 (19) |
C1—C2—C3—C4 | −0.5 (3) | C7—C8—C9—C10 | −56.2 (2) |
C2—C3—C4—C5 | 0.6 (3) | C8—C9—C10—C11 | 53.8 (2) |
C2—C3—C4—C7 | −178.30 (16) | C8—C9—C10—C13 | 177.63 (15) |
C3—C4—C5—C6 | 0.0 (3) | C13—C10—C11—C12 | −179.05 (15) |
C7—C4—C5—C6 | 178.89 (16) | C9—C10—C11—C12 | −54.3 (2) |
C2—C1—C6—C5 | 0.7 (3) | C10—C11—C12—C7 | 56.5 (2) |
O1—C1—C6—C5 | −179.91 (16) | C4—C7—C12—C11 | 178.71 (15) |
C4—C5—C6—C1 | −0.7 (3) | C8—C7—C12—C11 | −55.5 (2) |
C5—C4—C7—C8 | 128.81 (18) | C11—C10—C13—C14 | −175.11 (16) |
C3—C4—C7—C8 | −52.4 (2) | C9—C10—C13—C14 | 61.8 (2) |
C5—C4—C7—C12 | −107.56 (19) | C10—C13—C14—C15 | 176.55 (16) |
C3—C4—C7—C12 | 71.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O1i | 0.82 (1) | 2.06 (1) | 2.867 (3) | 168 (4) |
O1—H1A···O1ii | 0.82 (1) | 2.08 (1) | 2.893 (3) | 171 (4) |
Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x+1/2, −y−1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C15H22O |
Mr | 218.33 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 113 |
a, b, c (Å) | 35.062 (5), 5.3648 (6), 13.488 (2) |
β (°) | 98.994 (6) |
V (Å3) | 2505.9 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.20 × 0.14 × 0.10 |
Data collection | |
Diffractometer | Rigaku Saturn CCD diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2005) |
Tmin, Tmax | 0.986, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8805, 2182, 1824 |
Rint | 0.053 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.130, 1.13 |
No. of reflections | 2182 |
No. of parameters | 153 |
No. of restraints | 2 |
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: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), CrystalStructure (Rigaku/MSC, 2005).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O1i | 0.821 (10) | 2.060 (14) | 2.867 (3) | 168 (4) |
O1—H1A···O1ii | 0.817 (10) | 2.083 (12) | 2.893 (3) | 171 (4) |
Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x+1/2, −y−1/2, −z+1. |
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Phenol derivatives are widely used as starting materials for many products, including drugs and liquid crystalline materials (Eidenschink et al., 1978) and the crystal structure of 4-(4-n-propylcyclohexyl)phenol is reported herein, Fig. 1. The cyclohexyl ring adopts a chair conformation and the molecules were linked into dimers by O—H···O hydrogen bonds (Table 1).