In the title compound, C
17H
14O
3, the central ring is not planar and tends towards an envelope conformation. The hydroxy and oxopropyl groups facilitate one O—H
O and one C—H
O interactions, which link the molecules into molecular chains parallel to the
c direction. The packing is also stabilized by another C—H
O interaction, which interconnects the chains into a three-dimensional network.
Supporting information
CCDC reference: 193788
Key indicators
- Single-crystal X-ray study
- T = 213 K
- Mean (C-C) = 0.006 Å
- R factor = 0.055
- wR factor = 0.117
- Data-to-parameter ratio = 6.7
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
RINTA_01 Alert C The value of Rint is greater than 0.10
Rint given 0.120
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 24.99
From the CIF: _reflns_number_total 1226
Count of symmetry unique reflns 1229
Completeness (_total/calc) 99.76%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
10-Acetonyl-10-hydroxyphenanthren-9(10
H)-one
top
Crystal data top
C17H14O3 | Dx = 1.354 Mg m−3 |
Mr = 266.28 | Melting point: 340(1)K K |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2240 (8) Å | Cell parameters from 3007 reflections |
b = 15.2406 (9) Å | θ = 2.6–28.3° |
c = 9.2898 (8) Å | µ = 0.09 mm−1 |
V = 1305.9 (2) Å3 | T = 213 K |
Z = 4 | Needle, colorless |
F(000) = 560 | 0.50 × 0.18 × 0.10 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 980 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.120 |
Graphite monochromator | θmax = 25.0°, θmin = 2.6° |
Detector resolution: 8.33 pixels mm-1 | h = −10→9 |
ω scans | k = −18→16 |
5952 measured reflections | l = −11→10 |
1226 independent reflections | |
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)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0634P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
1226 reflections | Δρmax = 0.30 e Å−3 |
183 parameters | Δρmin = −0.34 e Å−3 |
1 restraint | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.021 (4) |
Special details top
Experimental. The data collection covered over a hemisphere of reciprocal space by a
combination of three sets of exposures; each set had a different φ angle (0,
88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω.
The crystal-to-detector distance was 5 cm and the detector swing angle was
-35°. Crystal decay was monitored by repeating fifty initial frames at the
end of data collection and analysing the intensity of duplicate reflections,
and was found to be negligible. |
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 | 0.0501 (3) | 0.37416 (18) | 0.2867 (3) | 0.0315 (8) | |
H1 | 0.1133 | 0.4119 | 0.2844 | 0.047* | |
O2 | 0.3128 (3) | 0.31552 (18) | 0.3639 (4) | 0.0349 (8) | |
O3 | 0.2477 (4) | 0.46586 (17) | 0.6171 (4) | 0.0444 (9) | |
C1 | 0.0604 (4) | 0.3271 (2) | 0.4160 (4) | 0.0239 (9) | |
C2 | 0.2106 (4) | 0.2861 (2) | 0.4311 (5) | 0.0230 (9) | |
C3 | 0.2247 (4) | 0.2131 (2) | 0.5344 (4) | 0.0232 (9) | |
C4 | 0.3618 (4) | 0.1933 (3) | 0.5897 (4) | 0.0312 (10) | |
H4 | 0.4421 | 0.2259 | 0.5614 | 0.037* | |
C5 | 0.3778 (6) | 0.1253 (3) | 0.6866 (5) | 0.0369 (12) | |
H5 | 0.4689 | 0.1114 | 0.7227 | 0.044* | |
C6 | 0.2576 (6) | 0.0780 (3) | 0.7294 (5) | 0.0409 (12) | |
H6 | 0.2682 | 0.0326 | 0.7954 | 0.049* | |
C7 | 0.1212 (5) | 0.0974 (3) | 0.6754 (5) | 0.0359 (11) | |
H7 | 0.0412 | 0.0656 | 0.7067 | 0.043* | |
C8 | 0.1031 (5) | 0.1645 (2) | 0.5740 (4) | 0.0256 (9) | |
C9 | −0.0384 (4) | 0.1817 (2) | 0.5047 (4) | 0.0268 (9) | |
C10 | −0.1540 (5) | 0.1219 (3) | 0.5120 (5) | 0.0347 (11) | |
H10 | −0.1433 | 0.0704 | 0.5648 | 0.042* | |
C11 | −0.2837 (5) | 0.1384 (3) | 0.4417 (6) | 0.0420 (12) | |
H11 | −0.3601 | 0.0989 | 0.4500 | 0.050* | |
C12 | −0.3002 (4) | 0.2136 (3) | 0.3592 (6) | 0.0414 (12) | |
H12 | −0.3872 | 0.2245 | 0.3118 | 0.050* | |
C13 | −0.1874 (4) | 0.2718 (3) | 0.3481 (5) | 0.0314 (10) | |
H13 | −0.1980 | 0.3218 | 0.2917 | 0.038* | |
C14 | −0.0569 (4) | 0.2572 (2) | 0.4199 (5) | 0.0241 (9) | |
C15 | 0.0355 (4) | 0.3887 (2) | 0.5472 (5) | 0.0238 (9) | |
H15A | −0.0644 | 0.4085 | 0.5461 | 0.029* | |
H15B | 0.0500 | 0.3553 | 0.6349 | 0.029* | |
C16 | 0.1340 (4) | 0.4684 (2) | 0.5506 (4) | 0.0259 (9) | |
C17 | 0.0901 (5) | 0.5475 (3) | 0.4704 (6) | 0.0397 (12) | |
H17A | 0.1597 | 0.5933 | 0.4862 | 0.060* | |
H17B | −0.0035 | 0.5665 | 0.5032 | 0.060* | |
H17C | 0.0854 | 0.5342 | 0.3695 | 0.060* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0312 (17) | 0.0382 (16) | 0.0250 (17) | −0.0014 (13) | −0.0013 (13) | 0.0105 (14) |
O2 | 0.0295 (16) | 0.0413 (16) | 0.0339 (17) | −0.0029 (12) | 0.0056 (15) | 0.0039 (16) |
O3 | 0.0326 (16) | 0.0422 (17) | 0.058 (2) | −0.0104 (16) | −0.0146 (15) | 0.0156 (17) |
C1 | 0.023 (2) | 0.024 (2) | 0.025 (2) | 0.0002 (15) | 0.0010 (16) | 0.0044 (19) |
C2 | 0.022 (2) | 0.028 (2) | 0.019 (2) | −0.0025 (16) | 0.0013 (18) | −0.0035 (19) |
C3 | 0.025 (2) | 0.0235 (19) | 0.021 (2) | 0.0055 (16) | 0.0003 (18) | −0.0067 (18) |
C4 | 0.033 (2) | 0.032 (2) | 0.029 (3) | 0.0057 (18) | −0.001 (2) | −0.008 (2) |
C5 | 0.046 (3) | 0.034 (3) | 0.031 (3) | 0.022 (2) | −0.007 (2) | −0.009 (2) |
C6 | 0.062 (3) | 0.030 (2) | 0.031 (3) | 0.014 (3) | −0.002 (2) | 0.001 (2) |
C7 | 0.050 (3) | 0.026 (2) | 0.032 (3) | 0.000 (2) | 0.008 (2) | 0.002 (2) |
C8 | 0.036 (2) | 0.016 (2) | 0.025 (2) | 0.0017 (16) | 0.0100 (18) | −0.0047 (18) |
C9 | 0.029 (2) | 0.026 (2) | 0.025 (2) | −0.0025 (17) | 0.0035 (18) | −0.0035 (18) |
C10 | 0.039 (3) | 0.029 (2) | 0.036 (3) | −0.0053 (19) | 0.015 (2) | −0.008 (2) |
C11 | 0.027 (2) | 0.048 (3) | 0.051 (3) | −0.013 (2) | 0.007 (2) | −0.019 (3) |
C12 | 0.024 (2) | 0.057 (3) | 0.043 (3) | −0.004 (2) | 0.000 (2) | −0.021 (3) |
C13 | 0.029 (2) | 0.034 (2) | 0.031 (2) | 0.0033 (18) | −0.002 (2) | −0.008 (2) |
C14 | 0.020 (2) | 0.029 (2) | 0.023 (2) | −0.0011 (15) | 0.0033 (17) | −0.0080 (19) |
C15 | 0.022 (2) | 0.022 (2) | 0.028 (2) | 0.0009 (15) | 0.0031 (18) | 0.0019 (17) |
C16 | 0.027 (2) | 0.025 (2) | 0.027 (2) | 0.0028 (16) | 0.003 (2) | 0.0011 (18) |
C17 | 0.041 (3) | 0.031 (2) | 0.048 (3) | −0.0018 (19) | −0.004 (2) | 0.010 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.402 (5) | C8—C9 | 1.479 (6) |
O1—H1 | 0.8200 | C9—C14 | 1.404 (5) |
O2—C2 | 1.217 (5) | C9—C10 | 1.404 (5) |
O3—C16 | 1.217 (5) | C10—C11 | 1.386 (6) |
C1—C14 | 1.519 (5) | C10—H10 | 0.9300 |
C1—C2 | 1.526 (5) | C11—C12 | 1.388 (7) |
C1—C15 | 1.556 (6) | C11—H11 | 0.9300 |
C2—C3 | 1.474 (5) | C12—C13 | 1.371 (5) |
C3—C8 | 1.394 (5) | C12—H12 | 0.9300 |
C3—C4 | 1.398 (5) | C13—C14 | 1.394 (5) |
C4—C5 | 1.380 (6) | C13—H13 | 0.9300 |
C4—H4 | 0.9300 | C15—C16 | 1.517 (5) |
C5—C6 | 1.381 (7) | C15—H15A | 0.9700 |
C5—H5 | 0.9300 | C15—H15B | 0.9700 |
C6—C7 | 1.386 (7) | C16—C17 | 1.474 (5) |
C6—H6 | 0.9300 | C17—H17A | 0.9600 |
C7—C8 | 1.400 (5) | C17—H17B | 0.9600 |
C7—H7 | 0.9300 | C17—H17C | 0.9600 |
| | | |
C1—O1—H1 | 109.5 | C11—C10—C9 | 121.0 (4) |
O1—C1—C14 | 109.3 (3) | C11—C10—H10 | 119.5 |
O1—C1—C2 | 110.5 (3) | C9—C10—H10 | 119.5 |
C14—C1—C2 | 110.9 (3) | C10—C11—C12 | 120.3 (4) |
O1—C1—C15 | 110.6 (3) | C10—C11—H11 | 119.8 |
C14—C1—C15 | 107.4 (3) | C12—C11—H11 | 119.8 |
C2—C1—C15 | 108.0 (3) | C13—C12—C11 | 119.5 (4) |
O2—C2—C3 | 122.9 (3) | C13—C12—H12 | 120.3 |
O2—C2—C1 | 120.3 (3) | C11—C12—H12 | 120.3 |
C3—C2—C1 | 116.7 (3) | C12—C13—C14 | 121.1 (4) |
C8—C3—C4 | 121.0 (4) | C12—C13—H13 | 119.5 |
C8—C3—C2 | 120.1 (3) | C14—C13—H13 | 119.5 |
C4—C3—C2 | 118.8 (3) | C13—C14—C9 | 120.3 (4) |
C5—C4—C3 | 119.9 (4) | C13—C14—C1 | 119.4 (3) |
C5—C4—H4 | 120.0 | C9—C14—C1 | 120.1 (3) |
C3—C4—H4 | 120.0 | C16—C15—C1 | 114.3 (3) |
C4—C5—C6 | 119.6 (4) | C16—C15—H15A | 108.7 |
C4—C5—H5 | 120.2 | C1—C15—H15A | 108.7 |
C6—C5—H5 | 120.2 | C16—C15—H15B | 108.7 |
C5—C6—C7 | 120.9 (4) | C1—C15—H15B | 108.7 |
C5—C6—H6 | 119.6 | H15A—C15—H15B | 107.6 |
C7—C6—H6 | 119.6 | O3—C16—C17 | 121.3 (3) |
C6—C7—C8 | 120.5 (4) | O3—C16—C15 | 120.1 (3) |
C6—C7—H7 | 119.7 | C17—C16—C15 | 118.6 (3) |
C8—C7—H7 | 119.7 | C16—C17—H17A | 109.5 |
C3—C8—C7 | 118.0 (4) | C16—C17—H17B | 109.5 |
C3—C8—C9 | 120.0 (3) | H17A—C17—H17B | 109.5 |
C7—C8—C9 | 121.9 (4) | C16—C17—H17C | 109.5 |
C14—C9—C10 | 117.8 (4) | H17A—C17—H17C | 109.5 |
C14—C9—C8 | 119.8 (3) | H17B—C17—H17C | 109.5 |
C10—C9—C8 | 122.2 (4) | | |
| | | |
O1—C1—C2—O2 | 21.4 (5) | C7—C8—C9—C10 | −13.8 (6) |
C14—C1—C2—O2 | 142.9 (4) | C14—C9—C10—C11 | −2.2 (6) |
C15—C1—C2—O2 | −99.6 (4) | C8—C9—C10—C11 | −177.7 (4) |
O1—C1—C2—C3 | −161.1 (3) | C9—C10—C11—C12 | 1.8 (6) |
C14—C1—C2—C3 | −39.7 (4) | C10—C11—C12—C13 | −0.3 (7) |
C15—C1—C2—C3 | 77.8 (4) | C11—C12—C13—C14 | −0.9 (7) |
O2—C2—C3—C8 | −160.0 (4) | C12—C13—C14—C9 | 0.4 (6) |
C1—C2—C3—C8 | 22.6 (5) | C12—C13—C14—C1 | −174.4 (4) |
O2—C2—C3—C4 | 19.2 (6) | C10—C9—C14—C13 | 1.1 (6) |
C1—C2—C3—C4 | −158.2 (4) | C8—C9—C14—C13 | 176.7 (4) |
C8—C3—C4—C5 | −0.8 (6) | C10—C9—C14—C1 | 175.9 (3) |
C2—C3—C4—C5 | 180.0 (4) | C8—C9—C14—C1 | −8.5 (5) |
C3—C4—C5—C6 | −0.8 (6) | O1—C1—C14—C13 | −29.8 (5) |
C4—C5—C6—C7 | 0.7 (7) | C2—C1—C14—C13 | −151.9 (4) |
C5—C6—C7—C8 | 1.1 (7) | C15—C1—C14—C13 | 90.3 (4) |
C4—C3—C8—C7 | 2.5 (5) | O1—C1—C14—C9 | 155.3 (3) |
C2—C3—C8—C7 | −178.3 (3) | C2—C1—C14—C9 | 33.2 (5) |
C4—C3—C8—C9 | −174.8 (4) | C15—C1—C14—C9 | −84.6 (4) |
C2—C3—C8—C9 | 4.4 (5) | O1—C1—C15—C16 | −54.5 (4) |
C6—C7—C8—C3 | −2.7 (6) | C14—C1—C15—C16 | −173.7 (3) |
C6—C7—C8—C9 | 174.5 (4) | C2—C1—C15—C16 | 66.6 (4) |
C3—C8—C9—C14 | −12.0 (6) | C1—C15—C16—O3 | −93.3 (5) |
C7—C8—C9—C14 | 170.8 (4) | C1—C15—C16—C17 | 85.8 (4) |
C3—C8—C9—C10 | 163.4 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3i | 0.82 | 2.18 | 2.813 (4) | 135 |
C15—H15B···O2ii | 0.97 | 2.55 | 3.444 (6) | 153 |
C17—H17B···O3iii | 0.96 | 2.57 | 3.446 (6) | 151 |
Symmetry codes: (i) −x+1/2, y, z−1/2; (ii) −x+1/2, y, z+1/2; (iii) x−1/2, −y+1, z. |