Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008039/bk1535sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008039/bk1535Isup2.hkl |
CCDC reference: 152641
Compound (I) was obtained as a finely crystalline white powder from a sample in Dr M. S. Newman's chemical collection. Slow evaporation of an ethanolic solution of this powder at room temperature produced suitable crystals. A synthesis of (I) is described by Fierens et al. (1955).
Difference Fourier methods were used to locate initial H-atom positions, including the hydroxyl-H atom, and the H atoms were refined. Refined C—H distances ranged from 0.97 (1) to 1.02 (1) Å with a mean value of 0.99 (2) Å; U(H)iso values ranged from 1.0 to 1.3 times the Ueq values of the attached C atoms. The H atoms, excepting the hydroxyl-H atom, were then made canonical, with C—H = 0.98 Å and U(H)iso = 1.2Ueq of the attached C atom. In the later stages of refinement the extinction coefficient was predicted to be negative, so it was not included in the model. The maximum peak in the final difference map occurs ~0.3 Å from C10, the maximum negative peak ~0.5 Å from C15.
Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1995); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN and PLATON (Spek, 1990).
C15H12O | Dx = 1.306 Mg m−3 |
Mr = 208.26 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, I41/a | Cell parameters from 29288 reflections |
Hall symbol: -I 4ad | θ = 2.6–27.5° |
a = 22.5868 (4) Å | µ = 0.08 mm−1 |
c = 8.3020 (1) Å | T = 150 K |
V = 4235.4 (1) Å3 | Uncut capped column, colourless |
Z = 16 | 0.38 × 0.23 × 0.23 mm |
F(000) = 1760 |
Nonius KappaCCD diffractometer | 2019 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.034 |
Graphite monochromator | θmax = 27.5° |
ω scans with κ offsets | h = −29→29 |
29288 measured reflections | k = −29→29 |
2431 independent reflections | l = −6→10 |
Refinement on F2 | 149 parameters |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.040 | Weighting scheme based on measured s.u.'s w = 1/[σ2cs + (0.034I)2] |
wR(F2) = 0.102 | (Δ/σ)max = 0.001 |
S = 1.92 | Δρmax = 0.25 e Å−3 |
2430 reflections | Δρmin = −0.22 e Å−3 |
C15H12O | Z = 16 |
Mr = 208.26 | Mo Kα radiation |
Tetragonal, I41/a | µ = 0.08 mm−1 |
a = 22.5868 (4) Å | T = 150 K |
c = 8.3020 (1) Å | 0.38 × 0.23 × 0.23 mm |
V = 4235.4 (1) Å3 |
Nonius KappaCCD diffractometer | 2019 reflections with I > 2σ(I) |
29288 measured reflections | Rint = 0.034 |
2431 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 149 parameters |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.92 | Δρmax = 0.25 e Å−3 |
2430 reflections | Δρmin = −0.22 e Å−3 |
Experimental. The Laue group assignment, the systematic absences and the centrosymmetry indicated by the intensity statistics led to assignment of the space group uniquely as I41/a (No. 88); since refinement proceeded well, it was adopted. Fourier difference methods were used to locate initial H atom positions, including the hydroxyl H atom, and the H atoms were refined. Refined C—H distances ranged from 0.97 (1) to 1.02 (1) Å, with mean value 0.99 (2) Å; their Uiso values ranged from 1.0 to 1.3 times the Ueq values of the attached C atoms. The H atoms, excepting the hydroxyl H atom, were then made canonical, with C—H = 0.98 Å and Uiso = 1.2 × Ueq of the attached C atom. In the later stages of refinement the extinction coefficient was predicted to be negative, so was not included in the model. The maximum peak in the final difference map occurs ~0.3 Å from C10, the maximum negative peak \sim 0.5 Å from C15. |
Geometry. Table of Least-Squares Planes —————————— ————– Plane number 1 ————— Atoms Defining Plane Distance e.s.d. C1 (1) 0.0085 0.0010 C2 (1) −0.0287 0.0011 C3 (1) 0.0108 0.0010 C4 (1) 0.0216 0.0009 C11 (1) 0.0251 0.0009 C12 (1) −0.0338 0.0009 Mean deviation from plane is 0.0214 angstroms Chi-squared: 3693.5 ————– Plane number 2 ————— Atoms Defining Plane Distance e.s.d. C5 (1) −0.0112 0.0010 C6 (1) −0.0184 0.0011 C7 (1) 0.0244 0.0011 C8 (1) 0.0071 0.0011 C13 (1) 0.0280 0.0009 C14 (1) −0.0265 0.0009 Mean deviation from plane is 0.0193 angstroms Chi-squared: 2648.7 Dihedral angles between least-squares planes plane plane angle 2 1 13.72 ————– Plane number 3 ————— Atoms Defining Plane Distance e.s.d. C9 (1) 0.0392 0.0010 C10 (1) −0.0268 0.0010 C11 (1) −0.0236 0.0009 C12 (1) 0.0529 0.0009 C13 (1) −0.0462 0.0009 C14 (1) 0.0099 0.0009 Mean deviation from plane is 0.0331 angstroms Chi-squared: 8737.4 Dihedral angles between least-squares planes plane plane angle 3 1 5.85 3 2 8.11 ————– Plane number 4 ————— Atoms Defining Plane Distance e.s.d. C1 (1) −0.1668 0.0010 C2 (1) −0.1156 0.0011 C3 (1) 0.1041 0.0010 C4 (1) 0.2091 0.0010 C5 (1) −0.1501 0.0010 C6 (1) −0.1782 0.0011 C7 (1) −0.0133 0.0011 C8 (1) 0.1108 0.0011 C9 (1) 0.0797 0.0010 C10 (1) −0.0482 0.0010 C11 (1) −0.0613 0.0009 C12 (1) 0.0647 0.0009 C13 (1) 0.0331 0.0009 C14 (1) 0.1024 0.0009 Additional Atoms Distance C15 (1) 0.5342 Mean deviation from plane is 0.1027 angstroms Chi-squared: 186430.9 Dihedral angles between least-squares planes plane plane angle 4 1 7.44 4 2 6.42 4 3 2.78 ————– Plane number 5 ————— Atoms Defining Plane Distance e.s.d. C1 (2) 0.1668 0.0010 C2 (2) 0.1156 0.0011 C3 (2) −0.1041 0.0010 C4 (2) −0.2091 0.0010 C5 (2) 0.1501 0.0010 C6 (2) 0.1782 0.0011 C7 (2) 0.0133 0.0011 C8 (2) −0.1108 0.0011 C9 (2) −0.0797 0.0010 C10 (2) 0.0482 0.0010 C11 (2) 0.0613 0.0009 C12 (2) −0.0647 0.0009 C13 (2) −0.0331 0.0009 C14 (2) −0.1024 0.0009 Mean deviation from plane is 0.1027 angstroms Chi-squared: 186431.0 Dihedral angles between least-squares planes plane plane angle 5 1 23.66 5 2 35.58 5 3 27.83 5 4 30.37 ————– Plane number 6 ————— Atoms Defining Plane Distance e.s.d. C1 (3) 0.1668 0.0010 C2 (3) 0.1156 0.0011 C3 (3) −0.1041 0.0010 C4 (3) −0.2091 0.0010 C5 (3) 0.1501 0.0010 C6 (3) 0.1782 0.0011 C7 (3) 0.0133 0.0011 C8 (3) −0.1108 0.0011 C9 (3) −0.0797 0.0010 C10 (3) 0.0482 0.0010 C11 (3) 0.0613 0.0009 C12 (3) −0.0647 0.0009 C13 (3) −0.0331 0.0009 C14 (3) −0.1024 0.0009 Mean deviation from plane is 0.1027 angstroms Chi-squared: 186431.0 Dihedral angles between least-squares planes plane plane angle 6 1 89.41 6 2 99.08 6 3 94.34 6 4 93.93 6 5 86.07 ————– Plane number 7 ————— Atoms Defining Plane Distance e.s.d. C1 (4) −0.1668 0.0010 C2 (4) −0.1156 0.0011 C3 (4) 0.1041 0.0010 C4 (4) 0.2091 0.0010 C5 (4) −0.1501 0.0010 C6 (4) −0.1782 0.0011 C7 (4) −0.0133 0.0011 C8 (4) 0.1108 0.0011 C9 (4) 0.0797 0.0010 C10 (4) −0.0482 0.0010 C11 (4) −0.0613 0.0009 C12 (4) 0.0647 0.0009 C13 (4) 0.0331 0.0009 C14 (4) 0.1024 0.0009 Mean deviation from plane is 0.1027 angstroms Chi-squared: 186430.9 Dihedral angles between least-squares planes plane plane angle 7 1 85.07 7 2 88.71 7 3 87.77 7 4 86.07 7 5 93.93 7 6 30.37 |
x | y | z | Uiso*/Ueq | ||
O1 | 0.30782 (3) | 0.49276 (3) | 0.08862 (9) | 0.0281 (2) | |
C1 | 0.42696 (5) | 0.48557 (5) | −0.4264 (1) | 0.0290 (3) | |
C2 | 0.38280 (5) | 0.52594 (5) | −0.4049 (1) | 0.0339 (3) | |
C3 | 0.36239 (4) | 0.53711 (5) | −0.2492 (1) | 0.0321 (3) | |
C4 | 0.38311 (4) | 0.50684 (4) | −0.1159 (1) | 0.0252 (3) | |
C5 | 0.42128 (5) | 0.41520 (4) | 0.1418 (1) | 0.0267 (3) | |
C6 | 0.44372 (5) | 0.37754 (5) | 0.2572 (1) | 0.0324 (3) | |
C7 | 0.49513 (5) | 0.34509 (5) | 0.2273 (1) | 0.0369 (3) | |
C8 | 0.52160 (5) | 0.34862 (5) | 0.0799 (1) | 0.0351 (3) | |
C9 | 0.52318 (4) | 0.38307 (4) | −0.2008 (1) | 0.0295 (3) | |
C10 | 0.49854 (5) | 0.41384 (5) | −0.3219 (1) | 0.0280 (3) | |
C11 | 0.45010 (4) | 0.45338 (4) | −0.2949 (1) | 0.0247 (3) | |
C12 | 0.42650 (4) | 0.46134 (4) | −0.1371 (1) | 0.0222 (3) | |
C13 | 0.44870 (4) | 0.42209 (4) | −0.0099 (1) | 0.0228 (3) | |
C14 | 0.49856 (4) | 0.38547 (4) | −0.0423 (1) | 0.0266 (3) | |
C15 | 0.35887 (5) | 0.52750 (4) | 0.0437 (1) | 0.0288 (3) | |
H1 | 0.4429 | 0.4788 | −0.5347 | 0.035* | |
H1O1 | 0.2891 (6) | 0.5136 (5) | 0.176 (2) | 0.058 (4)* | |
H2 | 0.3657 | 0.5468 | −0.4973 | 0.041* | |
H3 | 0.3321 | 0.5677 | −0.2337 | 0.038* | |
H5 | 0.3853 | 0.4378 | 0.1657 | 0.032* | |
H6 | 0.4234 | 0.3735 | 0.3609 | 0.039* | |
H7 | 0.5121 | 0.3199 | 0.3117 | 0.044* | |
H8 | 0.5572 | 0.3251 | 0.0584 | 0.042* | |
H9 | 0.5583 | 0.3588 | −0.2213 | 0.035* | |
H10 | 0.5141 | 0.4091 | −0.4314 | 0.034* | |
H15A | 0.3474 | 0.5692 | 0.0351 | 0.035* | |
H15B | 0.3895 | 0.5232 | 0.1265 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0251 (4) | 0.0278 (4) | 0.0313 (4) | −0.0012 (3) | 0.0045 (3) | −0.0053 (3) |
C1 | 0.0297 (6) | 0.0296 (6) | 0.0277 (6) | −0.0060 (5) | 0.0023 (4) | 0.0047 (5) |
C2 | 0.0334 (6) | 0.0315 (6) | 0.0368 (6) | −0.0016 (5) | −0.0008 (5) | 0.0118 (5) |
C3 | 0.0268 (6) | 0.0241 (6) | 0.0453 (7) | 0.0019 (4) | 0.0025 (5) | 0.0054 (5) |
C4 | 0.0226 (5) | 0.0190 (5) | 0.0340 (6) | −0.0044 (4) | 0.0018 (4) | −0.0006 (4) |
C5 | 0.0254 (5) | 0.0255 (6) | 0.0293 (6) | −0.0010 (4) | −0.0010 (4) | −0.0024 (4) |
C6 | 0.0340 (6) | 0.0349 (6) | 0.0282 (6) | −0.0020 (5) | −0.0028 (5) | 0.0015 (5) |
C7 | 0.0333 (6) | 0.0389 (7) | 0.0384 (7) | 0.0014 (5) | −0.0084 (5) | 0.0100 (5) |
C8 | 0.0250 (6) | 0.0356 (7) | 0.0446 (7) | 0.0049 (5) | −0.0021 (5) | 0.0056 (5) |
C9 | 0.0203 (5) | 0.0275 (6) | 0.0407 (6) | 0.0012 (5) | 0.0055 (5) | −0.0019 (5) |
C10 | 0.0257 (6) | 0.0267 (6) | 0.0316 (6) | −0.0048 (4) | 0.0073 (4) | −0.0023 (5) |
C11 | 0.0223 (5) | 0.0215 (5) | 0.0304 (6) | −0.0061 (4) | 0.0026 (4) | −0.0003 (4) |
C12 | 0.0184 (5) | 0.0191 (5) | 0.0291 (6) | −0.0050 (4) | 0.0000 (4) | −0.0017 (4) |
C13 | 0.0201 (5) | 0.0199 (5) | 0.0284 (5) | −0.0042 (4) | −0.0020 (4) | −0.0030 (4) |
C14 | 0.0202 (5) | 0.0241 (5) | 0.0356 (6) | −0.0028 (4) | −0.0009 (4) | 0.0002 (4) |
C15 | 0.0259 (5) | 0.0205 (5) | 0.0399 (6) | −0.0013 (4) | 0.0030 (5) | −0.0036 (5) |
O1—C15 | 1.444 (1) | C6—H6 | 0.98 |
O1—H1O1 | 0.96 (1) | C7—C8 | 1.364 (2) |
C1—C2 | 1.363 (2) | C7—H7 | 0.98 |
C1—C11 | 1.412 (1) | C8—C14 | 1.411 (2) |
C1—H1 | 0.98 | C8—H8 | 0.98 |
C2—C3 | 1.395 (1) | C9—C10 | 1.343 (1) |
C2—H2 | 0.98 | C9—C14 | 1.430 (1) |
C3—C4 | 1.382 (1) | C9—H9 | 0.98 |
C3—H3 | 0.98 | C10—C11 | 1.430 (1) |
C4—C12 | 1.431 (1) | C10—H10 | 0.98 |
C4—C15 | 1.508 (1) | C11—C12 | 1.426 (1) |
C5—C6 | 1.377 (1) | C12—C13 | 1.467 (1) |
C5—C13 | 1.412 (1) | C13—C14 | 1.423 (1) |
C5—H5 | 0.98 | C15—H15A | 0.98 |
C6—C7 | 1.395 (2) | C15—H15B | 0.98 |
C15—O1—H1O1 | 106.3 (8) | C10—C9—C14 | 120.56 (9) |
C2—C1—C11 | 120.92 (9) | C10—C9—H9 | 119.7 |
C2—C1—H1 | 119.5 | C14—C9—H9 | 119.7 |
C11—C1—H1 | 119.5 | C9—C10—C11 | 121.51 (9) |
C1—C2—C3 | 118.96 (9) | C9—C10—H10 | 119.2 |
C1—C2—H2 | 120.5 | C11—C10—H10 | 119.2 |
C3—C2—H2 | 120.5 | C1—C11—C10 | 118.91 (9) |
C2—C3—C4 | 122.7 (1) | C1—C11—C12 | 120.48 (9) |
C2—C3—H3 | 118.6 | C10—C11—C12 | 120.60 (9) |
C4—C3—H3 | 118.6 | C4—C12—C11 | 117.35 (9) |
C3—C4—C12 | 119.25 (9) | C4—C12—C13 | 125.42 (8) |
C3—C4—C15 | 115.32 (9) | C11—C12—C13 | 117.22 (9) |
C12—C4—C15 | 125.38 (9) | C5—C13—C12 | 123.97 (9) |
C6—C5—C13 | 121.8 (1) | C5—C13—C14 | 116.85 (9) |
C6—C5—H5 | 119.1 | C12—C13—C14 | 119.04 (9) |
C13—C5—H5 | 119.1 | C8—C14—C9 | 119.72 (9) |
C5—C6—C7 | 120.5 (1) | C8—C14—C13 | 119.90 (9) |
C5—C6—H6 | 119.8 | C9—C14—C13 | 120.26 (9) |
C7—C6—H6 | 119.8 | O1—C15—C4 | 110.42 (8) |
C6—C7—C8 | 119.6 (1) | O1—C15—H15A | 109.2 |
C6—C7—H7 | 120.2 | O1—C15—H15B | 109.2 |
C8—C7—H7 | 120.2 | C4—C15—H15A | 109.2 |
C7—C8—C14 | 121.2 (1) | C4—C15—H15B | 109.2 |
C7—C8—H8 | 119.4 | H15A—C15—H15B | 109.5 |
C14—C8—H8 | 119.4 | ||
O1—C15—C4—C3 | 93.8 (1) | C5—C13—C14—C8 | −5.7 (1) |
O1—C15—C4—C12 | −89.0 (1) | C5—C13—C14—C9 | 170.37 (9) |
C1—C2—C3—C4 | −3.2 (2) | C6—C5—C13—C12 | 179.71 (9) |
C1—C11—C10—C9 | 178.52 (9) | C6—C5—C13—C14 | 3.9 (1) |
C1—C11—C12—C4 | −5.9 (1) | C6—C7—C8—C14 | 1.3 (2) |
C1—C11—C12—C13 | 173.99 (9) | C7—C6—C5—C13 | 0.5 (2) |
C2—C1—C11—C10 | −176.7 (1) | C7—C8—C14—C9 | −172.8 (1) |
C2—C1—C11—C12 | 1.7 (1) | C7—C8—C14—C13 | 3.3 (2) |
C2—C3—C4—C12 | −1.2 (2) | C8—C14—C9—C10 | 174.1 (1) |
C2—C3—C4—C15 | 176.2 (1) | C8—C14—C13—C12 | 178.25 (9) |
C3—C2—C1—C11 | 2.9 (2) | C9—C10—C11—C12 | 0.1 (2) |
C3—C4—C12—C11 | 5.6 (1) | C9—C14—C13—C12 | −5.7 (1) |
C3—C4—C12—C13 | −174.32 (9) | C10—C9—C14—C13 | −2.0 (1) |
C4—C12—C11—C10 | 172.47 (8) | C10—C11—C12—C13 | −7.6 (1) |
C4—C12—C13—C5 | 14.4 (1) | C11—C10—C9—C14 | 4.9 (2) |
C4—C12—C13—C14 | −169.89 (9) | C11—C12—C4—C15 | −171.54 (9) |
C5—C6—C7—C8 | −3.2 (2) | C11—C12—C13—C14 | 10.2 (1) |
C5—C13—C12—C11 | −165.50 (9) | C13—C12—C4—C15 | 8.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O1i | 0.96 (1) | 1.83 (1) | 2.788 (1) | 176 (1) |
C2—H2···O1ii | 0.98 | 2.81 | 3.619 (1) | 140 |
C5—H5···O1 | 0.98 | 2.24 | 3.136 (1) | 152 |
Symmetry codes: (i) −y+3/4, x+1/4, z+1/4; (ii) −y+3/4, x+1/4, z−3/4. |
Experimental details
Crystal data | |
Chemical formula | C15H12O |
Mr | 208.26 |
Crystal system, space group | Tetragonal, I41/a |
Temperature (K) | 150 |
a, c (Å) | 22.5868 (4), 8.3020 (1) |
V (Å3) | 4235.4 (1) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.38 × 0.23 × 0.23 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29288, 2431, 2019 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.102, 1.92 |
No. of reflections | 2430 |
No. of parameters | 149 |
No. of restraints | ? |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.25, −0.22 |
Computer programs: COLLECT (Nonius, 1999), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS86 (Sheldrick, 1990), TEXSAN (Molecular Structure Corporation, 1995), ORTEPII (Johnson, 1976), TEXSAN and PLATON (Spek, 1990).
O1—C15 | 1.444 (1) | C4—C15 | 1.508 (1) |
C2—C1—C11 | 120.92 (9) | C9—C10—C11 | 121.51 (9) |
C1—C2—C3 | 118.96 (9) | C5—C13—C12 | 123.97 (9) |
C12—C4—C15 | 125.38 (9) | O1—C15—C4 | 110.42 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O1i | 0.96 (1) | 1.83 (1) | 2.788 (1) | 176 (1) |
C2—H2···O1ii | 0.98 | 2.81 | 3.619 (1) | 140 |
C5—H5···O1 | 0.98 | 2.24 | 3.136 (1) | 152 |
Symmetry codes: (i) −y+3/4, x+1/4, z+1/4; (ii) −y+3/4, x+1/4, z−3/4. |
a | b | c | |
a | C(2) | C22(8) | C21(8)[S(7)] |
b | C(6) | C21(9)[S(7)] | |
c | S(7) |
This report on the title compound, (I), is one of a series on hydrogen bonding and C—H···O interactions in aromatic compounds. \sch
Compound (I) crystallizes in the centrosymmetric space group I41/a with one molecule as the asymmetric unit. The refined molecule and the labelling scheme are given in Fig. 1. A single hydrogen bond and two leading C—H···O interactions (Taylor & Kennard, 1982; Steiner & Desiraju, 1998), one intramolecular, are present in this structure; geometric parameters are given in Table 2. These interactions link each molecule directly to four neighbours. The results of basic first- and second-level graph-set analysis (Bernstein et al., 1995) involving these interactions, labelled a-c for this purpose in the order of their appearance in Table 2, are given in Table 3. A l l the tabulated chains propagate along [001]. The molecules as a whole are divided into four sets, comprising those generated by space-group symmetry operators 1, 4, 5 and 8; 2, 3, 6 and 7; 9, 12, 14 and 15, and 10, 11, 13 and 16, which are `chained' within, but not between, these sets by each of the chain patterns. One example of each of these sets is included in the packing stereodiagram (Fig. 2), in which portions of the first-level a hydrogen-bond chains within these four sets are apparent.
In (I), the maximum deviations from planarity for each of the six-membered rings and the core as a whole are from ~1.2 to ~2.1 times as large as the corresponding values for the comparison molecule, phenanthrene-4-carboxylic acid, (II), at room temperature (Fitzgerald & Gerkin, 1998).
Selected bond distances and angles for (I) are given in Table 1. A l l distances and angles fall within normal limits. Corresponding pairs of chemically equivalent bonds (ignoring the substituent at C4) in the core of (I) are in good agreement, the r.m.s. difference within the seven pairs of distances being 0.008 Å. This value may be compared with the corresponding r.m.s. difference in (II) of 0.008 Å. Of the two remaining bonds in the core, C12—C13 is greater in both cases than C9—C10, by 0.124 (2) Å in (I) and by 0.132 (5) Å in (II). In (I) the closest intermolecular approaches, excluding pairs of atoms in hydrogen-bonded groups or the tabulated C—H···O interactions, are between C12 and H15Aiii [symmetry code: (iii) y − 1/4, 3/4 − x, z − 1/4] and fall short of the corresponding Bondi (1964) van der Waals radius sum by 0.06 Å. Two additional (smaller) shortfalls indicate a single noteworthy C—H···π interaction: C9—H9···(C5/C6/C7/C8/C14/C13)iv [symmetry code: (iv): 1/4 + y, 3/4 − x, −z − 1/4]. The (non-normalized) H9-centroid distance is 2.72 Å, while the H3-ring-atom distances range from 2.88 to 3.27 Å and the C9—H9···centroid angle is 161°. These values are consistent with those cited for significant C—H···π interactions, e.g. by Steiner et al. (1995).
It may be noted that, whereas in (II) approximately 4.5% of the molecules are found to be disordered (such that the substituted 4- and unsubstituted 5- positions are interchanged), in (I) there is no evidence for such disorder.
The preferential appearance of high symmetry in structures of monoalcohols has been discussed by Brock & Duncan (1994).