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In the title compound, C
17H
24O, the six-membered ring of the bicyclo[2.2.1]heptyl moiety has a boat conformation and the phenol group is in an equatorial position. In the crystal structure, centrosymmetric dimers are formed
via intermolecular O—H
O hydrogen bonds with rather unfavorable geometry.
Supporting information
CCDC reference: 263715
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.115
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C
GOODF01_ALERT_2_C The least squares goodness of fit parameter lies
outside the range 0.80 <> 2.00
Goodness of fit given = 0.785
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: P3 Diffractometer Control Program (Siemens, 1989); cell refinement: P3 Diffractometer Control Program; data reduction: XDISK (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.
2-Methyl-6-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)phenol
top
Crystal data top
C17H24O | Z = 2 |
Mr = 244.36 | F(000) = 268 |
Triclinic, P1 | Dx = 1.139 Mg m−3 |
a = 7.252 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.442 (4) Å | Cell parameters from 24 reflections |
c = 13.430 (8) Å | θ = 10–11° |
α = 93.49 (5)° | µ = 0.07 mm−1 |
β = 98.74 (5)° | T = 293 K |
γ = 94.56 (5)° | Prism, colorless |
V = 712.2 (7) Å3 | 0.50 × 0.20 × 0.20 mm |
Data collection top
Siemens P3 diffractometer | Rint = 0.046 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 2.8° |
Graphite monochromator | h = 0→8 |
θ/2θ scans | k = −8→8 |
2682 measured reflections | l = −15→15 |
2468 independent reflections | 2 standard reflections every 98 reflections |
1213 reflections with I > 2σ(I) | intensity decay: 3.2% |
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)] = 0.046 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 0.79 | w = 1/[σ2(Fo2) + (0.0657P)2] where P = (Fo2 + 2Fc2)/3 |
2468 reflections | (Δ/σ)max = 0.001 |
167 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
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 | Uiso*/Ueq | |
O1 | 0.1135 (2) | 1.0509 (2) | 0.09917 (11) | 0.0693 (5) | |
H1 | 0.0894 | 1.1063 | 0.0485 | 0.104* | |
C1 | 0.1553 (2) | 0.7100 (3) | 0.25582 (14) | 0.0455 (5) | |
C2 | 0.2219 (3) | 0.9166 (3) | 0.28556 (14) | 0.0469 (5) | |
H2 | 0.1086 | 0.9802 | 0.2720 | 0.056* | |
C3 | 0.2685 (3) | 0.9199 (3) | 0.40304 (15) | 0.0602 (6) | |
H3A | 0.4026 | 0.9384 | 0.4257 | 0.072* | |
H3B | 0.2082 | 1.0146 | 0.4350 | 0.072* | |
C4 | 0.1910 (3) | 0.7356 (3) | 0.42575 (15) | 0.0587 (6) | |
H4 | 0.2320 | 0.7050 | 0.4951 | 0.070* | |
C5 | −0.0227 (3) | 0.7193 (3) | 0.39441 (17) | 0.0685 (7) | |
H5A | −0.0753 | 0.8284 | 0.4157 | 0.082* | |
H5B | −0.0810 | 0.6171 | 0.4232 | 0.082* | |
C6 | −0.0496 (3) | 0.6913 (3) | 0.27821 (16) | 0.0585 (6) | |
H6A | −0.1220 | 0.7828 | 0.2469 | 0.070* | |
H6B | −0.1113 | 0.5726 | 0.2546 | 0.070* | |
C7 | 0.2546 (3) | 0.6092 (3) | 0.34419 (15) | 0.0508 (5) | |
C8 | 0.1769 (3) | 0.6386 (3) | 0.15080 (15) | 0.0642 (6) | |
H8A | 0.1304 | 0.5134 | 0.1404 | 0.096* | |
H8B | 0.3069 | 0.6509 | 0.1436 | 0.096* | |
H8C | 0.1072 | 0.7061 | 0.1018 | 0.096* | |
C9 | 0.4677 (3) | 0.6132 (3) | 0.34752 (19) | 0.0734 (7) | |
H9A | 0.5240 | 0.5735 | 0.4108 | 0.110* | |
H9B | 0.5180 | 0.7343 | 0.3406 | 0.110* | |
H9C | 0.4943 | 0.5344 | 0.2932 | 0.110* | |
C10 | 0.1826 (3) | 0.4117 (3) | 0.34688 (19) | 0.0748 (7) | |
H10A | 0.2522 | 0.3610 | 0.4034 | 0.112* | |
H10B | 0.1980 | 0.3457 | 0.2855 | 0.112* | |
H10C | 0.0524 | 0.4041 | 0.3535 | 0.112* | |
C11 | 0.3044 (3) | 1.0818 (3) | 0.13701 (15) | 0.0488 (5) | |
C12 | 0.3632 (3) | 1.0132 (2) | 0.23017 (14) | 0.0459 (5) | |
C13 | 0.5541 (3) | 1.0546 (3) | 0.26954 (17) | 0.0574 (6) | |
H13 | 0.6008 | 1.0162 | 0.3323 | 0.069* | |
C14 | 0.6734 (3) | 1.1505 (3) | 0.2174 (2) | 0.0690 (7) | |
H14 | 0.7995 | 1.1729 | 0.2446 | 0.083* | |
C15 | 0.6081 (3) | 1.2137 (3) | 0.12545 (19) | 0.0667 (6) | |
H15 | 0.6903 | 1.2797 | 0.0917 | 0.080* | |
C16 | 0.4219 (3) | 1.1800 (3) | 0.08299 (15) | 0.0562 (6) | |
C17 | 0.3468 (4) | 1.2500 (3) | −0.01680 (17) | 0.0770 (7) | |
H17A | 0.4478 | 1.3100 | −0.0442 | 0.115* | |
H17B | 0.2561 | 1.3339 | −0.0069 | 0.115* | |
H17C | 0.2886 | 1.1508 | −0.0629 | 0.115* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0487 (9) | 0.0920 (11) | 0.0651 (9) | 0.0051 (8) | −0.0028 (7) | 0.0209 (8) |
C1 | 0.0328 (10) | 0.0559 (12) | 0.0485 (11) | 0.0056 (9) | 0.0097 (8) | −0.0001 (9) |
C2 | 0.0402 (11) | 0.0523 (12) | 0.0489 (11) | 0.0096 (9) | 0.0082 (9) | 0.0011 (9) |
C3 | 0.0684 (15) | 0.0610 (14) | 0.0490 (12) | 0.0032 (11) | 0.0075 (11) | −0.0047 (10) |
C4 | 0.0629 (14) | 0.0685 (15) | 0.0458 (12) | 0.0084 (11) | 0.0088 (10) | 0.0080 (10) |
C5 | 0.0537 (14) | 0.0864 (17) | 0.0725 (15) | 0.0144 (12) | 0.0278 (12) | 0.0067 (12) |
C6 | 0.0339 (11) | 0.0744 (15) | 0.0695 (14) | 0.0060 (10) | 0.0133 (10) | 0.0080 (11) |
C7 | 0.0385 (11) | 0.0528 (12) | 0.0634 (13) | 0.0080 (9) | 0.0117 (9) | 0.0077 (10) |
C8 | 0.0656 (14) | 0.0693 (14) | 0.0562 (13) | −0.0037 (11) | 0.0156 (11) | −0.0099 (11) |
C9 | 0.0447 (13) | 0.0779 (17) | 0.1029 (18) | 0.0223 (12) | 0.0130 (12) | 0.0237 (14) |
C10 | 0.0718 (16) | 0.0624 (16) | 0.0946 (18) | 0.0092 (13) | 0.0227 (14) | 0.0135 (13) |
C11 | 0.0388 (12) | 0.0521 (12) | 0.0542 (12) | 0.0046 (9) | 0.0048 (10) | −0.0004 (10) |
C12 | 0.0385 (12) | 0.0460 (12) | 0.0521 (12) | 0.0062 (9) | 0.0040 (9) | −0.0004 (9) |
C13 | 0.0437 (13) | 0.0555 (13) | 0.0706 (14) | 0.0017 (10) | 0.0005 (11) | 0.0087 (11) |
C14 | 0.0355 (12) | 0.0648 (15) | 0.1035 (19) | −0.0008 (11) | 0.0038 (13) | 0.0055 (14) |
C15 | 0.0556 (16) | 0.0602 (14) | 0.0897 (18) | −0.0006 (11) | 0.0283 (13) | 0.0127 (13) |
C16 | 0.0607 (15) | 0.0519 (13) | 0.0599 (13) | 0.0120 (11) | 0.0193 (11) | 0.0024 (10) |
C17 | 0.097 (2) | 0.0777 (16) | 0.0641 (15) | 0.0180 (14) | 0.0268 (14) | 0.0183 (12) |
Geometric parameters (Å, º) top
O1—C11 | 1.396 (2) | C8—H8A | 0.9600 |
O1—H1 | 0.8200 | C8—H8B | 0.9600 |
C1—C8 | 1.512 (3) | C8—H8C | 0.9600 |
C1—C6 | 1.557 (3) | C9—H9A | 0.9600 |
C1—C7 | 1.557 (3) | C9—H9B | 0.9600 |
C1—C2 | 1.582 (3) | C9—H9C | 0.9600 |
C2—C12 | 1.517 (3) | C10—H10A | 0.9600 |
C2—C3 | 1.561 (3) | C10—H10B | 0.9600 |
C2—H2 | 0.9800 | C10—H10C | 0.9600 |
C3—C4 | 1.507 (3) | C11—C16 | 1.393 (3) |
C3—H3A | 0.9700 | C11—C12 | 1.399 (3) |
C3—H3B | 0.9700 | C12—C13 | 1.407 (3) |
C4—C5 | 1.536 (3) | C13—C14 | 1.376 (3) |
C4—C7 | 1.547 (3) | C13—H13 | 0.9300 |
C4—H4 | 0.9800 | C14—C15 | 1.378 (3) |
C5—C6 | 1.542 (3) | C14—H14 | 0.9300 |
C5—H5A | 0.9700 | C15—C16 | 1.381 (3) |
C5—H5B | 0.9700 | C15—H15 | 0.9300 |
C6—H6A | 0.9700 | C16—C17 | 1.507 (3) |
C6—H6B | 0.9700 | C17—H17A | 0.9600 |
C7—C10 | 1.525 (3) | C17—H17B | 0.9600 |
C7—C9 | 1.537 (3) | C17—H17C | 0.9600 |
| | | |
C11—O1—H1 | 109.5 | C1—C8—H8A | 109.5 |
C8—C1—C6 | 114.38 (17) | C1—C8—H8B | 109.5 |
C8—C1—C7 | 115.72 (17) | H8A—C8—H8B | 109.5 |
C6—C1—C7 | 100.24 (16) | C1—C8—H8C | 109.5 |
C8—C1—C2 | 116.42 (17) | H8A—C8—H8C | 109.5 |
C6—C1—C2 | 103.67 (15) | H8B—C8—H8C | 109.5 |
C7—C1—C2 | 104.42 (15) | C7—C9—H9A | 109.5 |
C12—C2—C3 | 117.86 (17) | C7—C9—H9B | 109.5 |
C12—C2—C1 | 119.89 (15) | H9A—C9—H9B | 109.5 |
C3—C2—C1 | 101.80 (16) | C7—C9—H9C | 109.5 |
C12—C2—H2 | 105.3 | H9A—C9—H9C | 109.5 |
C3—C2—H2 | 105.3 | H9B—C9—H9C | 109.5 |
C1—C2—H2 | 105.3 | C7—C10—H10A | 109.5 |
C4—C3—C2 | 103.41 (16) | C7—C10—H10B | 109.5 |
C4—C3—H3A | 111.1 | H10A—C10—H10B | 109.5 |
C2—C3—H3A | 111.1 | C7—C10—H10C | 109.5 |
C4—C3—H3B | 111.1 | H10A—C10—H10C | 109.5 |
C2—C3—H3B | 111.1 | H10B—C10—H10C | 109.5 |
H3A—C3—H3B | 109.0 | C16—C11—O1 | 119.50 (19) |
C3—C4—C5 | 108.57 (19) | C16—C11—C12 | 124.36 (19) |
C3—C4—C7 | 102.79 (17) | O1—C11—C12 | 116.12 (18) |
C5—C4—C7 | 102.44 (17) | C11—C12—C13 | 115.15 (19) |
C3—C4—H4 | 114.0 | C11—C12—C2 | 120.20 (17) |
C5—C4—H4 | 114.0 | C13—C12—C2 | 124.44 (19) |
C7—C4—H4 | 114.0 | C14—C13—C12 | 121.6 (2) |
C4—C5—C6 | 103.67 (16) | C14—C13—H13 | 119.2 |
C4—C5—H5A | 111.0 | C12—C13—H13 | 119.2 |
C6—C5—H5A | 111.0 | C13—C14—C15 | 120.8 (2) |
C4—C5—H5B | 111.0 | C13—C14—H14 | 119.6 |
C6—C5—H5B | 111.0 | C15—C14—H14 | 119.6 |
H5A—C5—H5B | 109.0 | C14—C15—C16 | 120.6 (2) |
C5—C6—C1 | 102.76 (16) | C14—C15—H15 | 119.7 |
C5—C6—H6A | 111.2 | C16—C15—H15 | 119.7 |
C1—C6—H6A | 111.2 | C15—C16—C11 | 117.4 (2) |
C5—C6—H6B | 111.2 | C15—C16—C17 | 121.6 (2) |
C1—C6—H6B | 111.2 | C11—C16—C17 | 121.0 (2) |
H6A—C6—H6B | 109.1 | C16—C17—H17A | 109.5 |
C10—C7—C9 | 106.57 (18) | C16—C17—H17B | 109.5 |
C10—C7—C4 | 113.25 (18) | H17A—C17—H17B | 109.5 |
C9—C7—C4 | 115.10 (18) | C16—C17—H17C | 109.5 |
C10—C7—C1 | 115.46 (18) | H17A—C17—H17C | 109.5 |
C9—C7—C1 | 113.42 (17) | H17B—C17—H17C | 109.5 |
C4—C7—C1 | 92.99 (15) | | |
| | | |
C8—C1—C2—C12 | −22.5 (2) | C8—C1—C7—C9 | 59.9 (2) |
C6—C1—C2—C12 | −149.02 (17) | C6—C1—C7—C9 | −176.55 (17) |
C7—C1—C2—C12 | 106.41 (19) | C2—C1—C7—C9 | −69.4 (2) |
C8—C1—C2—C3 | −154.63 (17) | C8—C1—C7—C4 | 178.95 (17) |
C6—C1—C2—C3 | 78.85 (18) | C6—C1—C7—C4 | −57.50 (17) |
C7—C1—C2—C3 | −25.71 (17) | C2—C1—C7—C4 | 49.62 (16) |
C12—C2—C3—C4 | −143.72 (17) | C16—C11—C12—C13 | 1.8 (3) |
C1—C2—C3—C4 | −10.38 (19) | O1—C11—C12—C13 | −176.62 (16) |
C2—C3—C4—C5 | −64.4 (2) | C16—C11—C12—C2 | 176.70 (17) |
C2—C3—C4—C7 | 43.6 (2) | O1—C11—C12—C2 | −1.7 (3) |
C3—C4—C5—C6 | 75.5 (2) | C3—C2—C12—C11 | −152.90 (17) |
C7—C4—C5—C6 | −32.8 (2) | C1—C2—C12—C11 | 82.3 (2) |
C4—C5—C6—C1 | −4.3 (2) | C3—C2—C12—C13 | 21.5 (3) |
C8—C1—C6—C5 | 163.92 (18) | C1—C2—C12—C13 | −103.3 (2) |
C7—C1—C6—C5 | 39.4 (2) | C11—C12—C13—C14 | −2.1 (3) |
C2—C1—C6—C5 | −68.3 (2) | C2—C12—C13—C14 | −176.79 (19) |
C3—C4—C7—C10 | −176.56 (17) | C12—C13—C14—C15 | 1.7 (3) |
C5—C4—C7—C10 | −63.9 (2) | C13—C14—C15—C16 | −0.9 (3) |
C3—C4—C7—C9 | 60.5 (2) | C14—C15—C16—C11 | 0.5 (3) |
C5—C4—C7—C9 | 173.10 (19) | C14—C15—C16—C17 | 179.1 (2) |
C3—C4—C7—C1 | −57.16 (18) | O1—C11—C16—C15 | 177.33 (18) |
C5—C4—C7—C1 | 55.46 (18) | C12—C11—C16—C15 | −1.0 (3) |
C8—C1—C7—C10 | −63.5 (2) | O1—C11—C16—C17 | −1.3 (3) |
C6—C1—C7—C10 | 60.1 (2) | C12—C11—C16—C17 | −179.65 (18) |
C2—C1—C7—C10 | 167.18 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O1i | 0.82 | 2.45 | 2.933 (3) | 118 |
Symmetry code: (i) −x, −y+2, −z. |
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