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In the title compound, C17H14O3, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201351X/cv6132sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680201351X/cv6132Isup2.hkl
Contains datablock I

CCDC reference: 193788

Key indicators

  • Single-crystal X-ray study
  • T = 213 K
  • Mean [sigma](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


Yellow Alert 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

Computing details top

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(10H)-one top
Crystal data top
C17H14O3Dx = 1.354 Mg m3
Mr = 266.28Melting point: 340(1)K K
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
a = 9.2240 (8) ÅCell parameters from 3007 reflections
b = 15.2406 (9) Åθ = 2.6–28.3°
c = 9.2898 (8) ŵ = 0.09 mm1
V = 1305.9 (2) Å3T = 213 K
Z = 4Needle, colorless
F(000) = 5600.50 × 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 tubeRint = 0.120
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
Detector resolution: 8.33 pixels mm-1h = 109
ω scansk = 1816
5952 measured reflectionsl = 1110
1226 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-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 reflectionsΔρmax = 0.30 e Å3
183 parametersΔρmin = 0.34 e Å3
1 restraintExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
O10.0501 (3)0.37416 (18)0.2867 (3)0.0315 (8)
H10.11330.41190.28440.047*
O20.3128 (3)0.31552 (18)0.3639 (4)0.0349 (8)
O30.2477 (4)0.46586 (17)0.6171 (4)0.0444 (9)
C10.0604 (4)0.3271 (2)0.4160 (4)0.0239 (9)
C20.2106 (4)0.2861 (2)0.4311 (5)0.0230 (9)
C30.2247 (4)0.2131 (2)0.5344 (4)0.0232 (9)
C40.3618 (4)0.1933 (3)0.5897 (4)0.0312 (10)
H40.44210.22590.56140.037*
C50.3778 (6)0.1253 (3)0.6866 (5)0.0369 (12)
H50.46890.11140.72270.044*
C60.2576 (6)0.0780 (3)0.7294 (5)0.0409 (12)
H60.26820.03260.79540.049*
C70.1212 (5)0.0974 (3)0.6754 (5)0.0359 (11)
H70.04120.06560.70670.043*
C80.1031 (5)0.1645 (2)0.5740 (4)0.0256 (9)
C90.0384 (4)0.1817 (2)0.5047 (4)0.0268 (9)
C100.1540 (5)0.1219 (3)0.5120 (5)0.0347 (11)
H100.14330.07040.56480.042*
C110.2837 (5)0.1384 (3)0.4417 (6)0.0420 (12)
H110.36010.09890.45000.050*
C120.3002 (4)0.2136 (3)0.3592 (6)0.0414 (12)
H120.38720.22450.31180.050*
C130.1874 (4)0.2718 (3)0.3481 (5)0.0314 (10)
H130.19800.32180.29170.038*
C140.0569 (4)0.2572 (2)0.4199 (5)0.0241 (9)
C150.0355 (4)0.3887 (2)0.5472 (5)0.0238 (9)
H15A0.06440.40850.54610.029*
H15B0.05000.35530.63490.029*
C160.1340 (4)0.4684 (2)0.5506 (4)0.0259 (9)
C170.0901 (5)0.5475 (3)0.4704 (6)0.0397 (12)
H17A0.15970.59330.48620.060*
H17B0.00350.56650.50320.060*
H17C0.08540.53420.36950.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0312 (17)0.0382 (16)0.0250 (17)0.0014 (13)0.0013 (13)0.0105 (14)
O20.0295 (16)0.0413 (16)0.0339 (17)0.0029 (12)0.0056 (15)0.0039 (16)
O30.0326 (16)0.0422 (17)0.058 (2)0.0104 (16)0.0146 (15)0.0156 (17)
C10.023 (2)0.024 (2)0.025 (2)0.0002 (15)0.0010 (16)0.0044 (19)
C20.022 (2)0.028 (2)0.019 (2)0.0025 (16)0.0013 (18)0.0035 (19)
C30.025 (2)0.0235 (19)0.021 (2)0.0055 (16)0.0003 (18)0.0067 (18)
C40.033 (2)0.032 (2)0.029 (3)0.0057 (18)0.001 (2)0.008 (2)
C50.046 (3)0.034 (3)0.031 (3)0.022 (2)0.007 (2)0.009 (2)
C60.062 (3)0.030 (2)0.031 (3)0.014 (3)0.002 (2)0.001 (2)
C70.050 (3)0.026 (2)0.032 (3)0.000 (2)0.008 (2)0.002 (2)
C80.036 (2)0.016 (2)0.025 (2)0.0017 (16)0.0100 (18)0.0047 (18)
C90.029 (2)0.026 (2)0.025 (2)0.0025 (17)0.0035 (18)0.0035 (18)
C100.039 (3)0.029 (2)0.036 (3)0.0053 (19)0.015 (2)0.008 (2)
C110.027 (2)0.048 (3)0.051 (3)0.013 (2)0.007 (2)0.019 (3)
C120.024 (2)0.057 (3)0.043 (3)0.004 (2)0.000 (2)0.021 (3)
C130.029 (2)0.034 (2)0.031 (2)0.0033 (18)0.002 (2)0.008 (2)
C140.020 (2)0.029 (2)0.023 (2)0.0011 (15)0.0033 (17)0.0080 (19)
C150.022 (2)0.022 (2)0.028 (2)0.0009 (15)0.0031 (18)0.0019 (17)
C160.027 (2)0.025 (2)0.027 (2)0.0028 (16)0.003 (2)0.0011 (18)
C170.041 (3)0.031 (2)0.048 (3)0.0018 (19)0.004 (2)0.010 (2)
Geometric parameters (Å, º) top
O1—C11.402 (5)C8—C91.479 (6)
O1—H10.8200C9—C141.404 (5)
O2—C21.217 (5)C9—C101.404 (5)
O3—C161.217 (5)C10—C111.386 (6)
C1—C141.519 (5)C10—H100.9300
C1—C21.526 (5)C11—C121.388 (7)
C1—C151.556 (6)C11—H110.9300
C2—C31.474 (5)C12—C131.371 (5)
C3—C81.394 (5)C12—H120.9300
C3—C41.398 (5)C13—C141.394 (5)
C4—C51.380 (6)C13—H130.9300
C4—H40.9300C15—C161.517 (5)
C5—C61.381 (7)C15—H15A0.9700
C5—H50.9300C15—H15B0.9700
C6—C71.386 (7)C16—C171.474 (5)
C6—H60.9300C17—H17A0.9600
C7—C81.400 (5)C17—H17B0.9600
C7—H70.9300C17—H17C0.9600
C1—O1—H1109.5C11—C10—C9121.0 (4)
O1—C1—C14109.3 (3)C11—C10—H10119.5
O1—C1—C2110.5 (3)C9—C10—H10119.5
C14—C1—C2110.9 (3)C10—C11—C12120.3 (4)
O1—C1—C15110.6 (3)C10—C11—H11119.8
C14—C1—C15107.4 (3)C12—C11—H11119.8
C2—C1—C15108.0 (3)C13—C12—C11119.5 (4)
O2—C2—C3122.9 (3)C13—C12—H12120.3
O2—C2—C1120.3 (3)C11—C12—H12120.3
C3—C2—C1116.7 (3)C12—C13—C14121.1 (4)
C8—C3—C4121.0 (4)C12—C13—H13119.5
C8—C3—C2120.1 (3)C14—C13—H13119.5
C4—C3—C2118.8 (3)C13—C14—C9120.3 (4)
C5—C4—C3119.9 (4)C13—C14—C1119.4 (3)
C5—C4—H4120.0C9—C14—C1120.1 (3)
C3—C4—H4120.0C16—C15—C1114.3 (3)
C4—C5—C6119.6 (4)C16—C15—H15A108.7
C4—C5—H5120.2C1—C15—H15A108.7
C6—C5—H5120.2C16—C15—H15B108.7
C5—C6—C7120.9 (4)C1—C15—H15B108.7
C5—C6—H6119.6H15A—C15—H15B107.6
C7—C6—H6119.6O3—C16—C17121.3 (3)
C6—C7—C8120.5 (4)O3—C16—C15120.1 (3)
C6—C7—H7119.7C17—C16—C15118.6 (3)
C8—C7—H7119.7C16—C17—H17A109.5
C3—C8—C7118.0 (4)C16—C17—H17B109.5
C3—C8—C9120.0 (3)H17A—C17—H17B109.5
C7—C8—C9121.9 (4)C16—C17—H17C109.5
C14—C9—C10117.8 (4)H17A—C17—H17C109.5
C14—C9—C8119.8 (3)H17B—C17—H17C109.5
C10—C9—C8122.2 (4)
O1—C1—C2—O221.4 (5)C7—C8—C9—C1013.8 (6)
C14—C1—C2—O2142.9 (4)C14—C9—C10—C112.2 (6)
C15—C1—C2—O299.6 (4)C8—C9—C10—C11177.7 (4)
O1—C1—C2—C3161.1 (3)C9—C10—C11—C121.8 (6)
C14—C1—C2—C339.7 (4)C10—C11—C12—C130.3 (7)
C15—C1—C2—C377.8 (4)C11—C12—C13—C140.9 (7)
O2—C2—C3—C8160.0 (4)C12—C13—C14—C90.4 (6)
C1—C2—C3—C822.6 (5)C12—C13—C14—C1174.4 (4)
O2—C2—C3—C419.2 (6)C10—C9—C14—C131.1 (6)
C1—C2—C3—C4158.2 (4)C8—C9—C14—C13176.7 (4)
C8—C3—C4—C50.8 (6)C10—C9—C14—C1175.9 (3)
C2—C3—C4—C5180.0 (4)C8—C9—C14—C18.5 (5)
C3—C4—C5—C60.8 (6)O1—C1—C14—C1329.8 (5)
C4—C5—C6—C70.7 (7)C2—C1—C14—C13151.9 (4)
C5—C6—C7—C81.1 (7)C15—C1—C14—C1390.3 (4)
C4—C3—C8—C72.5 (5)O1—C1—C14—C9155.3 (3)
C2—C3—C8—C7178.3 (3)C2—C1—C14—C933.2 (5)
C4—C3—C8—C9174.8 (4)C15—C1—C14—C984.6 (4)
C2—C3—C8—C94.4 (5)O1—C1—C15—C1654.5 (4)
C6—C7—C8—C32.7 (6)C14—C1—C15—C16173.7 (3)
C6—C7—C8—C9174.5 (4)C2—C1—C15—C1666.6 (4)
C3—C8—C9—C1412.0 (6)C1—C15—C16—O393.3 (5)
C7—C8—C9—C14170.8 (4)C1—C15—C16—C1785.8 (4)
C3—C8—C9—C10163.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.822.182.813 (4)135
C15—H15B···O2ii0.972.553.444 (6)153
C17—H17B···O3iii0.962.573.446 (6)151
Symmetry codes: (i) x+1/2, y, z1/2; (ii) x+1/2, y, z+1/2; (iii) x1/2, y+1, z.
 

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