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The title compound, C13H12O3, crystallizes in the monoclinic system, with two independent mol­ecules in the asymmetric unit. In one of the mol­ecules, the phenyl ring forms a dihedral angle of 23.93 (5)° with the pentenedione plane, while in the other, the dihedral angle is 13.33 (5)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802011091/ci6138sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802011091/ci6138Isup2.hkl
Contains datablock I

CCDC reference: 189918

Key indicators

  • Single-crystal X-ray study
  • T = 213 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.054
  • wR factor = 0.127
  • Data-to-parameter ratio = 18.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); 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).

3-Acetyl-1-phenyl-2-pentene-1,4-dione top
Crystal data top
C13H12O3F(000) = 912
Mr = 216.23Dx = 1.262 Mg m3
Monoclinic, P21/cMelting point: 344(1) K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 14.1314 (2) ÅCell parameters from 8192 reflections
b = 15.0764 (1) Åθ = 2.5–28.3°
c = 10.9229 (2) ŵ = 0.09 mm1
β = 102.015 (1)°T = 213 K
V = 2276.15 (6) Å3Block, yellow
Z = 80.50 × 0.40 × 0.40 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3634 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.090
Graphite monochromatorθmax = 28.2°, θmin = 2.5°
Detector resolution: 8.33 pixels mm-1h = 1815
ω scansk = 2019
13416 measured reflectionsl = 1414
5495 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)] = 0.054H-atom parameters constrained
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0326P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max < 0.001
5495 reflectionsΔρmax = 0.36 e Å3
294 parametersΔρmin = 0.30 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.030 (2)
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
O1A0.70013 (8)0.44246 (7)0.37046 (11)0.0408 (3)
O2A0.79247 (9)0.26580 (7)0.29755 (11)0.0445 (3)
O3A0.75921 (8)0.12262 (7)0.49852 (10)0.0423 (3)
C1A0.44024 (11)0.42942 (10)0.35007 (13)0.0318 (3)
H1A0.43380.37000.37000.038*
C2A0.35863 (12)0.48287 (11)0.31892 (14)0.0371 (4)
H2A0.29770.45910.31790.044*
C3A0.36757 (13)0.57135 (11)0.28942 (14)0.0387 (4)
H3A0.31290.60710.26920.046*
C4A0.45831 (13)0.60665 (10)0.29002 (14)0.0390 (4)
H4A0.46430.66590.26950.047*
C5A0.53957 (12)0.55409 (9)0.32099 (13)0.0316 (3)
H5A0.60020.57830.32160.038*
C6A0.53158 (11)0.46464 (9)0.35154 (12)0.0255 (3)
C7A0.62283 (11)0.41212 (9)0.38526 (12)0.0266 (3)
C8A0.62067 (10)0.32116 (9)0.43882 (12)0.0264 (3)
H8A0.56520.30240.46470.032*
C9A0.69630 (10)0.26562 (9)0.45079 (12)0.0260 (3)
C10A0.78801 (11)0.28538 (10)0.40420 (14)0.0328 (3)
C11A0.87101 (13)0.32176 (13)0.49775 (19)0.0548 (5)
H11A0.92140.33970.45600.082*
H11B0.89530.27700.55870.082*
H11C0.84980.37210.53880.082*
C12A0.69612 (11)0.17534 (9)0.50963 (12)0.0277 (3)
C13A0.61884 (12)0.15345 (10)0.57959 (15)0.0385 (4)
H13A0.63090.09580.61700.058*
H13B0.55700.15350.52290.058*
H13C0.61890.19690.64390.058*
O1B0.07014 (8)0.20897 (7)0.63765 (11)0.0456 (3)
O2B0.26615 (10)0.30166 (8)0.70769 (13)0.0572 (4)
O3B0.38900 (8)0.23511 (7)0.50601 (12)0.0479 (3)
C1B0.07596 (11)0.03239 (9)0.65384 (13)0.0301 (3)
H1B0.13180.04380.62410.036*
C2B0.02397 (12)0.10227 (10)0.68966 (15)0.0361 (4)
H2B0.04520.16030.68420.043*
C3B0.05928 (12)0.08583 (10)0.73348 (15)0.0395 (4)
H3B0.09440.13280.75670.047*
C4B0.09068 (12)0.00085 (11)0.74290 (16)0.0409 (4)
H4B0.14650.01180.77300.049*
C5B0.03904 (11)0.07064 (10)0.70768 (15)0.0345 (4)
H5B0.06030.12850.71420.041*
C6B0.04505 (10)0.05500 (9)0.66218 (13)0.0254 (3)
C7B0.09728 (11)0.13265 (9)0.62452 (13)0.0288 (3)
C8B0.18514 (10)0.11880 (9)0.57082 (13)0.0288 (3)
H8B0.19830.06230.54450.035*
C9B0.24560 (10)0.18537 (9)0.55947 (13)0.0281 (3)
C10B0.23342 (11)0.27994 (10)0.60053 (16)0.0363 (4)
C11B0.18601 (16)0.34300 (12)0.5007 (2)0.0603 (6)
H11D0.19210.40240.53300.091*
H11E0.11870.32820.47480.091*
H11F0.21670.33890.43040.091*
C12B0.33492 (11)0.17180 (10)0.50777 (14)0.0324 (3)
C13B0.35610 (13)0.08211 (10)0.46202 (17)0.0418 (4)
H13D0.41290.08510.42680.063*
H13E0.30220.06250.39920.063*
H13F0.36690.04100.53070.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0332 (6)0.0326 (6)0.0619 (8)0.0001 (5)0.0217 (6)0.0024 (5)
O2A0.0455 (7)0.0454 (7)0.0503 (7)0.0091 (5)0.0280 (6)0.0012 (5)
O3A0.0442 (7)0.0323 (6)0.0535 (7)0.0158 (5)0.0172 (6)0.0049 (5)
C1A0.0340 (8)0.0289 (8)0.0342 (8)0.0006 (6)0.0106 (6)0.0026 (6)
C2A0.0307 (9)0.0449 (10)0.0361 (8)0.0032 (7)0.0082 (7)0.0007 (7)
C3A0.0430 (10)0.0430 (9)0.0298 (8)0.0186 (8)0.0070 (7)0.0023 (7)
C4A0.0557 (11)0.0267 (8)0.0361 (8)0.0104 (7)0.0129 (8)0.0041 (6)
C5A0.0395 (9)0.0250 (7)0.0333 (8)0.0011 (6)0.0143 (7)0.0003 (6)
C6A0.0323 (8)0.0231 (7)0.0230 (7)0.0033 (6)0.0101 (6)0.0022 (5)
C7A0.0299 (8)0.0238 (7)0.0289 (7)0.0014 (6)0.0126 (6)0.0033 (5)
C8A0.0277 (8)0.0244 (7)0.0295 (7)0.0012 (6)0.0116 (6)0.0017 (5)
C9A0.0270 (8)0.0250 (7)0.0268 (7)0.0019 (6)0.0078 (6)0.0030 (5)
C10A0.0273 (8)0.0294 (8)0.0432 (9)0.0079 (6)0.0109 (7)0.0060 (6)
C11A0.0302 (10)0.0634 (13)0.0674 (13)0.0042 (9)0.0021 (9)0.0079 (9)
C12A0.0294 (8)0.0259 (7)0.0279 (7)0.0045 (6)0.0060 (6)0.0021 (5)
C13A0.0433 (10)0.0316 (8)0.0443 (9)0.0038 (7)0.0175 (7)0.0062 (7)
O1B0.0407 (7)0.0235 (6)0.0799 (9)0.0025 (5)0.0295 (6)0.0002 (5)
O2B0.0565 (8)0.0517 (8)0.0656 (9)0.0118 (6)0.0177 (7)0.0258 (6)
O3B0.0359 (7)0.0350 (6)0.0792 (9)0.0098 (5)0.0266 (6)0.0005 (6)
C1B0.0265 (8)0.0269 (7)0.0401 (8)0.0017 (6)0.0139 (6)0.0018 (6)
C2B0.0387 (9)0.0250 (7)0.0469 (9)0.0004 (6)0.0142 (7)0.0032 (6)
C3B0.0386 (9)0.0338 (9)0.0495 (10)0.0085 (7)0.0167 (8)0.0056 (7)
C4B0.0283 (8)0.0434 (10)0.0569 (10)0.0004 (7)0.0222 (8)0.0042 (8)
C5B0.0289 (8)0.0303 (8)0.0479 (9)0.0039 (6)0.0163 (7)0.0005 (7)
C6B0.0213 (7)0.0247 (7)0.0314 (7)0.0012 (5)0.0080 (6)0.0004 (6)
C7B0.0258 (8)0.0237 (7)0.0380 (8)0.0008 (6)0.0094 (6)0.0010 (6)
C8B0.0274 (8)0.0237 (7)0.0378 (8)0.0011 (6)0.0125 (6)0.0009 (6)
C9B0.0259 (8)0.0258 (7)0.0335 (7)0.0007 (6)0.0087 (6)0.0007 (6)
C10B0.0295 (8)0.0277 (8)0.0562 (10)0.0057 (6)0.0196 (8)0.0036 (7)
C11B0.0700 (14)0.0322 (9)0.0876 (15)0.0084 (9)0.0364 (12)0.0156 (9)
C12B0.0297 (8)0.0293 (8)0.0413 (8)0.0036 (6)0.0144 (7)0.0017 (6)
C13B0.0402 (10)0.0361 (9)0.0572 (10)0.0018 (7)0.0289 (8)0.0043 (7)
Geometric parameters (Å, º) top
O1A—C7A1.2255 (17)O1B—C7B1.2307 (16)
O2A—C10A1.2161 (18)O2B—C10B1.2107 (19)
O3A—C12A1.2191 (17)O3B—C12B1.2254 (17)
C1A—C2A1.390 (2)C1B—C2B1.387 (2)
C1A—C6A1.393 (2)C1B—C6B1.3969 (19)
C1A—H1A0.93C1B—H1B0.93
C2A—C3A1.384 (2)C2B—C3B1.382 (2)
C2A—H2A0.93C2B—H2B0.93
C3A—C4A1.387 (2)C3B—C4B1.391 (2)
C3A—H3A0.93C3B—H3B0.93
C4A—C5A1.378 (2)C4B—C5B1.380 (2)
C4A—H4A0.93C4B—H4B0.93
C5A—C6A1.3994 (18)C5B—C6B1.4002 (19)
C5A—H5A0.93C5B—H5B0.93
C6A—C7A1.492 (2)C6B—C7B1.4868 (19)
C7A—C8A1.4938 (18)C7B—C8B1.494 (2)
C8A—C9A1.3424 (19)C8B—C9B1.3404 (19)
C8A—H8A0.93C8B—H8B0.93
C9A—C12A1.5055 (19)C9B—C12B1.500 (2)
C9A—C10A1.517 (2)C9B—C10B1.515 (2)
C10A—C11A1.491 (2)C10B—C11B1.496 (2)
C11A—H11A0.96C11B—H11D0.96
C11A—H11B0.96C11B—H11E0.96
C11A—H11C0.96C11B—H11F0.96
C12A—C13A1.494 (2)C12B—C13B1.493 (2)
C13A—H13A0.96C13B—H13D0.96
C13A—H13B0.96C13B—H13E0.96
C13A—H13C0.96C13B—H13F0.96
C2A—C1A—C6A120.11 (14)C2B—C1B—C6B120.47 (14)
C2A—C1A—H1A119.9C2B—C1B—H1B119.8
C6A—C1A—H1A119.9C6B—C1B—H1B119.8
C3A—C2A—C1A120.29 (15)C3B—C2B—C1B120.05 (14)
C3A—C2A—H2A119.9C3B—C2B—H2B120.0
C1A—C2A—H2A119.9C1B—C2B—H2B120.0
C2A—C3A—C4A119.85 (15)C2B—C3B—C4B120.12 (14)
C2A—C3A—H3A120.1C2B—C3B—H3B119.9
C4A—C3A—H3A120.1C4B—C3B—H3B119.9
C5A—C4A—C3A120.19 (14)C5B—C4B—C3B120.03 (15)
C5A—C4A—H4A119.9C5B—C4B—H4B120.0
C3A—C4A—H4A119.9C3B—C4B—H4B120.0
C4A—C5A—C6A120.54 (15)C4B—C5B—C6B120.51 (14)
C4A—C5A—H5A119.7C4B—C5B—H5B119.7
C6A—C5A—H5A119.7C6B—C5B—H5B119.7
C1A—C6A—C5A119.03 (13)C1B—C6B—C5B118.81 (13)
C1A—C6A—C7A123.48 (12)C1B—C6B—C7B122.99 (13)
C5A—C6A—C7A117.49 (13)C5B—C6B—C7B118.20 (12)
O1A—C7A—C6A121.16 (12)O1B—C7B—C6B121.28 (13)
O1A—C7A—C8A119.06 (13)O1B—C7B—C8B118.75 (13)
C6A—C7A—C8A119.78 (12)C6B—C7B—C8B119.97 (12)
C9A—C8A—C7A122.01 (13)C9B—C8B—C7B121.97 (13)
C9A—C8A—H8A119.0C9B—C8B—H8B119.0
C7A—C8A—H8A119.0C7B—C8B—H8B119.0
C8A—C9A—C12A122.25 (13)C8B—C9B—C12B122.35 (13)
C8A—C9A—C10A124.27 (13)C8B—C9B—C10B124.29 (13)
C12A—C9A—C10A113.46 (12)C12B—C9B—C10B113.33 (12)
O2A—C10A—C11A123.77 (16)O2B—C10B—C11B123.76 (16)
O2A—C10A—C9A119.46 (14)O2B—C10B—C9B119.77 (15)
C11A—C10A—C9A116.58 (14)C11B—C10B—C9B116.34 (15)
C10A—C11A—H11A109.5C10B—C11B—H11D109.5
C10A—C11A—H11B109.5C10B—C11B—H11E109.5
H11A—C11A—H11B109.5H11D—C11B—H11E109.5
C10A—C11A—H11C109.5C10B—C11B—H11F109.5
H11A—C11A—H11C109.5H11D—C11B—H11F109.5
H11B—C11A—H11C109.5H11E—C11B—H11F109.5
O3A—C12A—C13A122.31 (13)O3B—C12B—C13B122.07 (14)
O3A—C12A—C9A118.73 (13)O3B—C12B—C9B118.42 (14)
C13A—C12A—C9A118.97 (12)C13B—C12B—C9B119.50 (12)
C12A—C13A—H13A109.5C12B—C13B—H13D109.5
C12A—C13A—H13B109.5C12B—C13B—H13E109.5
H13A—C13A—H13B109.5H13D—C13B—H13E109.5
C12A—C13A—H13C109.5C12B—C13B—H13F109.5
H13A—C13A—H13C109.5H13D—C13B—H13F109.5
H13B—C13A—H13C109.5H13E—C13B—H13F109.5
C6A—C1A—C2A—C3A0.1 (2)C6B—C1B—C2B—C3B0.3 (2)
C1A—C2A—C3A—C4A0.5 (2)C1B—C2B—C3B—C4B0.6 (2)
C2A—C3A—C4A—C5A0.6 (2)C2B—C3B—C4B—C5B0.4 (2)
C3A—C4A—C5A—C6A0.3 (2)C3B—C4B—C5B—C6B0.1 (2)
C2A—C1A—C6A—C5A0.2 (2)C2B—C1B—C6B—C5B0.2 (2)
C2A—C1A—C6A—C7A179.30 (13)C2B—C1B—C6B—C7B179.61 (14)
C4A—C5A—C6A—C1A0.1 (2)C4B—C5B—C6B—C1B0.4 (2)
C4A—C5A—C6A—C7A179.43 (13)C4B—C5B—C6B—C7B179.45 (14)
C1A—C6A—C7A—O1A170.86 (13)C1B—C6B—C7B—O1B177.14 (14)
C5A—C6A—C7A—O1A9.67 (19)C5B—C6B—C7B—O1B3.0 (2)
C1A—C6A—C7A—C8A9.5 (2)C1B—C6B—C7B—C8B2.2 (2)
C5A—C6A—C7A—C8A169.93 (12)C5B—C6B—C7B—C8B177.62 (13)
O1A—C7A—C8A—C9A12.0 (2)O1B—C7B—C8B—C9B13.3 (2)
C6A—C7A—C8A—C9A168.43 (13)C6B—C7B—C8B—C9B166.06 (13)
C7A—C8A—C9A—C12A177.38 (12)C7B—C8B—C9B—C12B178.90 (13)
C7A—C8A—C9A—C10A4.4 (2)C7B—C8B—C9B—C10B1.0 (2)
C8A—C9A—C10A—O2A88.41 (18)C8B—C9B—C10B—O2B86.5 (2)
C12A—C9A—C10A—O2A89.91 (16)C12B—C9B—C10B—O2B91.59 (18)
C8A—C9A—C10A—C11A96.37 (18)C8B—C9B—C10B—C11B97.45 (18)
C12A—C9A—C10A—C11A85.31 (16)C12B—C9B—C10B—C11B84.48 (17)
C8A—C9A—C12A—O3A167.58 (14)C8B—C9B—C12B—O3B176.52 (14)
C10A—C9A—C12A—O3A10.78 (19)C10B—C9B—C12B—O3B1.6 (2)
C8A—C9A—C12A—C13A12.5 (2)C8B—C9B—C12B—C13B2.6 (2)
C10A—C9A—C12A—C13A169.18 (13)C10B—C9B—C12B—C13B179.30 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1B—H1B···O3Ai0.932.543.415 (2)158
Symmetry code: (i) x+1, y, z+1.
 

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