The crystal structure of the title compound, C
16H
18O
2, contains one molecule in the asymmetric unit. With the exception of the C(CH
3)
2 group, it is nearly planar. The intermolecular hydrogen bond formed by the hydroxy group with the O-carbonyl atom [O
O = 2.720 Å and O—H
O = 166°] links the molecules into infinite chains.
Supporting information
CCDC reference: 232137
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.004 Å
- R factor = 0.032
- wR factor = 0.108
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT026_ALERT_3_A Ratio Observed / Unique Reflections too Low .... 26 Perc.
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.98
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.132
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
2 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO & SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
Crystal data top
C16H18O2 | F(000) = 520 |
Mr = 242.30 | Dx = 1.182 Mg m−3 |
Monoclinic, P21/n | Melting point = 455–456 K |
Hall symbol: -p 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 14.693 (3) Å | Cell parameters from 16335 reflections |
b = 6.0684 (12) Å | θ = 1.9–25.0° |
c = 15.266 (3) Å | µ = 0.08 mm−1 |
β = 90.58 (3)° | T = 291 K |
V = 1361.1 (5) Å3 | Needle, yellow |
Z = 4 | 0.38 × 0.06 × 0.06 mm |
Data collection top
Nonius KappaCCD diffractometer | 616 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.132 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
ω scans | h = −14→17 |
16335 measured reflections | k = −7→7 |
2351 independent reflections | l = −18→18 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.108 | w = exp[8(sinθ/λ)2)]/σ2(Fo2) |
S = 0.96 | (Δ/σ)max < 0.001 |
2351 reflections | Δρmax = 0.09 e Å−3 |
167 parameters | Δρmin = −0.10 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0087 (14) |
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 | 0.81570 (18) | 0.4803 (4) | −0.16313 (16) | 0.0781 (8) | |
H1 | 0.8299 | 0.3938 | −0.2020 | 0.117* | |
O2 | 0.39124 (17) | −0.7229 (4) | 0.21129 (13) | 0.0695 (8) | |
C1 | 0.7637 (2) | 0.3731 (6) | −0.1023 (2) | 0.0585 (10) | |
C2 | 0.7268 (2) | 0.1696 (6) | −0.1185 (2) | 0.0611 (10) | |
H2 | 0.7353 | 0.1020 | −0.1725 | 0.073* | |
C3 | 0.6768 (2) | 0.0647 (5) | −0.0540 (2) | 0.0593 (10) | |
H3 | 0.6517 | −0.0730 | −0.0655 | 0.071* | |
C4 | 0.6636 (2) | 0.1615 (5) | 0.0277 (2) | 0.0523 (9) | |
C5 | 0.6998 (2) | 0.3693 (5) | 0.0408 (2) | 0.0615 (10) | |
H5 | 0.6907 | 0.4395 | 0.0941 | 0.074* | |
C6 | 0.7495 (2) | 0.4761 (5) | −0.0235 (2) | 0.0635 (10) | |
H6 | 0.7729 | 0.6162 | −0.0133 | 0.076* | |
C7 | 0.6175 (2) | 0.0494 (5) | 0.0992 (2) | 0.0585 (10) | |
H7 | 0.6195 | 0.1193 | 0.1534 | 0.070* | |
C8 | 0.5726 (2) | −0.1416 (6) | 0.0959 (2) | 0.0583 (9) | |
H8 | 0.5669 | −0.2083 | 0.0413 | 0.070* | |
C9 | 0.5320 (2) | −0.2551 (5) | 0.1693 (2) | 0.0538 (9) | |
C10 | 0.4823 (2) | −0.4373 (5) | 0.1560 (2) | 0.0574 (9) | |
H10 | 0.4768 | −0.4914 | 0.0992 | 0.069* | |
C11 | 0.4365 (2) | −0.5546 (6) | 0.2256 (2) | 0.0570 (9) | |
C12 | 0.4447 (2) | −0.4606 (5) | 0.31584 (19) | 0.0638 (10) | |
H12A | 0.4394 | −0.5794 | 0.3580 | 0.077* | |
H12B | 0.3945 | −0.3600 | 0.3252 | 0.077* | |
C13 | 0.5346 (2) | −0.3371 (5) | 0.3333 (2) | 0.0624 (10) | |
C14 | 0.5456 (2) | −0.1684 (5) | 0.26047 (19) | 0.0622 (10) | |
H14A | 0.5025 | −0.0500 | 0.2699 | 0.075* | |
H14B | 0.6062 | −0.1059 | 0.2649 | 0.075* | |
C15 | 0.6143 (3) | −0.5013 (6) | 0.3352 (2) | 0.0877 (13) | |
H15A | 0.6699 | −0.4238 | 0.3473 | 0.132* | |
H15B | 0.6183 | −0.5734 | 0.2794 | 0.132* | |
H15C | 0.6042 | −0.6091 | 0.3801 | 0.132* | |
C16 | 0.5291 (3) | −0.2168 (5) | 0.42195 (19) | 0.0909 (13) | |
H16A | 0.4769 | −0.1218 | 0.4219 | 0.136* | |
H16B | 0.5832 | −0.1306 | 0.4310 | 0.136* | |
H16C | 0.5238 | −0.3231 | 0.4682 | 0.136* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0793 (19) | 0.0783 (18) | 0.0773 (18) | −0.0031 (16) | 0.0338 (15) | 0.0062 (14) |
O2 | 0.0753 (19) | 0.0712 (17) | 0.0624 (15) | −0.0174 (14) | 0.0183 (13) | −0.0089 (13) |
C1 | 0.058 (3) | 0.059 (2) | 0.059 (2) | 0.003 (2) | 0.017 (2) | 0.003 (2) |
C2 | 0.062 (3) | 0.073 (3) | 0.049 (2) | 0.003 (2) | 0.0151 (18) | −0.0067 (19) |
C3 | 0.056 (2) | 0.067 (3) | 0.054 (2) | −0.0030 (19) | 0.0092 (19) | −0.0041 (19) |
C4 | 0.053 (2) | 0.055 (2) | 0.050 (2) | 0.0001 (19) | 0.0125 (17) | 0.0001 (18) |
C5 | 0.067 (3) | 0.062 (3) | 0.056 (2) | 0.000 (2) | 0.0151 (19) | −0.0060 (19) |
C6 | 0.066 (3) | 0.054 (2) | 0.071 (2) | 0.0028 (19) | 0.015 (2) | −0.007 (2) |
C7 | 0.062 (3) | 0.061 (2) | 0.052 (2) | 0.000 (2) | 0.0107 (18) | −0.0019 (18) |
C8 | 0.057 (2) | 0.068 (3) | 0.050 (2) | −0.002 (2) | 0.0098 (18) | −0.0038 (19) |
C9 | 0.054 (2) | 0.061 (2) | 0.047 (2) | 0.0054 (18) | 0.0097 (17) | −0.0034 (19) |
C10 | 0.058 (2) | 0.067 (3) | 0.047 (2) | −0.003 (2) | 0.0104 (17) | −0.0038 (18) |
C11 | 0.055 (3) | 0.060 (2) | 0.056 (2) | 0.002 (2) | 0.0106 (18) | −0.0047 (19) |
C12 | 0.074 (3) | 0.066 (2) | 0.052 (2) | −0.003 (2) | 0.0130 (18) | −0.0034 (18) |
C13 | 0.072 (3) | 0.069 (2) | 0.047 (2) | −0.008 (2) | 0.0035 (18) | −0.0003 (19) |
C14 | 0.061 (2) | 0.069 (2) | 0.057 (2) | −0.004 (2) | 0.0121 (18) | −0.0025 (19) |
C15 | 0.083 (3) | 0.100 (3) | 0.081 (3) | 0.000 (3) | −0.011 (2) | 0.005 (2) |
C16 | 0.122 (4) | 0.099 (3) | 0.053 (2) | −0.029 (3) | 0.011 (2) | −0.014 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.373 (4) | C9—C14 | 1.499 (4) |
O1—H1 | 0.820 | C10—C11 | 1.450 (4) |
O2—C11 | 1.237 (3) | C10—H10 | 0.930 |
C1—C2 | 1.370 (4) | C11—C12 | 1.494 (4) |
C1—C6 | 1.373 (4) | C12—C13 | 1.540 (4) |
C2—C3 | 1.389 (4) | C12—H12A | 0.970 |
C2—H2 | 0.930 | C12—H12B | 0.970 |
C3—C4 | 1.393 (4) | C13—C14 | 1.521 (4) |
C3—H3 | 0.930 | C13—C15 | 1.537 (4) |
C4—C5 | 1.383 (4) | C13—C16 | 1.541 (4) |
C4—C7 | 1.459 (4) | C14—H14A | 0.970 |
C5—C6 | 1.389 (4) | C14—H14B | 0.970 |
C5—H5 | 0.930 | C15—H15A | 0.960 |
C6—H6 | 0.930 | C15—H15B | 0.960 |
C7—C8 | 1.334 (4) | C15—H15C | 0.960 |
C7—H7 | 0.930 | C16—H16A | 0.960 |
C8—C9 | 1.449 (4) | C16—H16B | 0.960 |
C8—H8 | 0.930 | C16—H16C | 0.960 |
C9—C10 | 1.340 (4) | | |
| | | |
C1—O1—H1 | 109.5 | O2—C11—C12 | 121.1 (3) |
C2—C1—C6 | 120.4 (3) | C10—C11—C12 | 117.0 (3) |
C2—C1—O1 | 121.8 (3) | C11—C12—C13 | 114.0 (3) |
C6—C1—O1 | 117.9 (3) | C11—C12—H12A | 108.8 |
C1—C2—C3 | 119.7 (3) | C13—C12—H12A | 108.8 |
C1—C2—H2 | 120.1 | C11—C12—H12B | 108.8 |
C3—C2—H2 | 120.1 | C13—C12—H12B | 108.8 |
C2—C3—C4 | 121.4 (3) | H12A—C12—H12B | 107.6 |
C2—C3—H3 | 119.3 | C14—C13—C15 | 111.3 (3) |
C4—C3—H3 | 119.3 | C14—C13—C16 | 109.3 (3) |
C5—C4—C3 | 117.2 (3) | C15—C13—C16 | 109.7 (3) |
C5—C4—C7 | 119.9 (3) | C14—C13—C12 | 107.3 (3) |
C3—C4—C7 | 122.9 (3) | C15—C13—C12 | 109.8 (3) |
C4—C5—C6 | 121.8 (3) | C16—C13—C12 | 109.3 (3) |
C4—C5—H5 | 119.1 | C9—C14—C13 | 115.4 (3) |
C6—C5—H5 | 119.1 | C9—C14—H14A | 108.4 |
C1—C6—C5 | 119.4 (3) | C13—C14—H14A | 108.4 |
C1—C6—H6 | 120.3 | C9—C14—H14B | 108.4 |
C5—C6—H6 | 120.3 | C13—C14—H14B | 108.4 |
C8—C7—C4 | 127.6 (3) | H14A—C14—H14B | 107.5 |
C8—C7—H7 | 116.2 | C13—C15—H15A | 109.5 |
C4—C7—H7 | 116.2 | C13—C15—H15B | 109.5 |
C7—C8—C9 | 126.2 (3) | H15A—C15—H15B | 109.5 |
C7—C8—H8 | 116.9 | C13—C15—H15C | 109.5 |
C9—C8—H8 | 116.9 | H15A—C15—H15C | 109.5 |
C10—C9—C8 | 120.2 (3) | H15B—C15—H15C | 109.5 |
C10—C9—C14 | 119.8 (3) | C13—C16—H16A | 109.5 |
C8—C9—C14 | 119.9 (3) | C13—C16—H16B | 109.5 |
C9—C10—C11 | 123.4 (3) | H16A—C16—H16B | 109.5 |
C9—C10—H10 | 118.3 | C13—C16—H16C | 109.5 |
C11—C10—H10 | 118.3 | H16A—C16—H16C | 109.5 |
O2—C11—C10 | 121.9 (3) | H16B—C16—H16C | 109.5 |
| | | |
C6—C1—C2—C3 | −1.7 (5) | C8—C9—C10—C11 | −177.4 (3) |
O1—C1—C2—C3 | 178.2 (3) | C14—C9—C10—C11 | 2.6 (5) |
C1—C2—C3—C4 | −0.4 (5) | C9—C10—C11—O2 | −179.8 (3) |
C2—C3—C4—C5 | 2.0 (5) | C9—C10—C11—C12 | 1.4 (5) |
C2—C3—C4—C7 | −175.2 (3) | O2—C11—C12—C13 | 150.5 (3) |
C3—C4—C5—C6 | −1.6 (5) | C10—C11—C12—C13 | −30.7 (4) |
C7—C4—C5—C6 | 175.7 (3) | C11—C12—C13—C14 | 52.6 (4) |
C2—C1—C6—C5 | 2.0 (5) | C11—C12—C13—C15 | −68.6 (4) |
O1—C1—C6—C5 | −177.8 (3) | C11—C12—C13—C16 | 171.0 (3) |
C4—C5—C6—C1 | −0.3 (5) | C10—C9—C14—C13 | 23.3 (5) |
C5—C4—C7—C8 | 174.1 (3) | C8—C9—C14—C13 | −156.6 (3) |
C3—C4—C7—C8 | −8.8 (5) | C15—C13—C14—C9 | 71.2 (4) |
C4—C7—C8—C9 | 176.1 (3) | C16—C13—C14—C9 | −167.4 (3) |
C7—C8—C9—C10 | 174.5 (3) | C12—C13—C14—C9 | −49.0 (4) |
C7—C8—C9—C14 | −5.5 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.91 | 2.718 (3) | 166 |
Symmetry code: (i) x+1/2, −y−1/2, z−1/2. |