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The title mol­ecule, C16H14O3, is slightly distorted from planarity, the dihedral angle between the two benzene rings being 9.51 (7)°. The configuration of the keto group with respect to the olefinic double bond is s-cis. O—H...O hydrogen bonds, and C—H...O and π–π interactions, link the mol­ecules to form a three-dimensional network. The C—H...O interactions form rings of graph-set motifs S(5), R_{2}^{1}(6) and R_{2}^{1}(7).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001698/wn6322sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001698/wn6322Isup2.hkl
Contains datablock I

CCDC reference: 264093

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.044
  • wR factor = 0.126
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT480_ALERT_4_C Long H...A H-Bond Reported H1 .. O2 .. 2.86 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. O3 .. 2.72 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H14 .. O1 .. 2.93 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H14 .. O2 .. 2.63 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H16A .. O1 .. 2.82 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H16C .. O3 .. 2.68 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C15 .. O1 .. 99.00 Deg.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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 and PLATON (Spek, 2003).

1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-ene-1-one top
Crystal data top
C16H14O3F(000) = 1072
Mr = 254.27Dx = 1.317 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 6162 reflections
a = 13.4346 (8) Åθ = 4.9–54.7°
b = 11.4998 (7) ŵ = 0.09 mm1
c = 16.6055 (10) ÅT = 293 K
V = 2565.5 (3) Å3Block, colourless
Z = 80.59 × 0.41 × 0.28 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
2513 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 28.3°, θmin = 2.5°
ω scansh = 1617
15000 measured reflectionsk = 1015
3015 independent reflectionsl = 2122
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)] = 0.044H-atom parameters constrained
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0671P)2 + 0.4382P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
3015 reflectionsΔρmax = 0.19 e Å3
175 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0097 (13)
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
xyzUiso*/Ueq
O10.29376 (7)0.63939 (9)0.08155 (6)0.0562 (3)
O20.43974 (7)0.06151 (9)0.36966 (6)0.0586 (3)
O30.17087 (6)0.67671 (9)0.01419 (7)0.0562 (3)
H30.17350.73380.01530.084*
C10.45688 (9)0.31078 (11)0.23901 (8)0.0448 (3)
H10.50700.35300.21380.054*
C20.48204 (9)0.21708 (12)0.28625 (8)0.0487 (3)
H20.54850.19650.29260.058*
C30.40830 (9)0.15332 (11)0.32447 (7)0.0424 (3)
C40.30962 (9)0.18459 (12)0.31520 (8)0.0489 (3)
H40.25980.14250.34090.059*
C50.28576 (9)0.27863 (12)0.26760 (8)0.0497 (3)
H50.21920.29910.26170.060*
C60.35787 (9)0.34405 (10)0.22805 (7)0.0401 (3)
C70.33350 (9)0.44287 (11)0.17658 (7)0.0429 (3)
H70.38660.48380.15450.051*
C80.24320 (10)0.47962 (12)0.15846 (8)0.0504 (3)
H80.18910.43990.18000.060*
C90.22370 (9)0.58009 (11)0.10598 (8)0.0425 (3)
C100.11971 (8)0.60669 (10)0.08370 (7)0.0388 (3)
C110.03902 (9)0.54121 (11)0.11133 (7)0.0433 (3)
H110.05050.47920.14610.052*
C120.05700 (9)0.56614 (11)0.08838 (8)0.0460 (3)
H120.10950.52140.10770.055*
C130.07549 (9)0.65788 (10)0.03645 (7)0.0409 (3)
C140.00312 (9)0.72515 (11)0.00864 (8)0.0431 (3)
H140.00890.78750.02570.052*
C150.09898 (9)0.69932 (11)0.03210 (8)0.0441 (3)
H150.15120.74480.01310.053*
C160.36787 (13)0.00137 (14)0.41476 (11)0.0679 (4)
H16A0.40070.05940.44670.102*
H16B0.32190.03830.37860.102*
H16C0.33250.05110.44940.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0375 (5)0.0584 (6)0.0726 (7)0.0033 (4)0.0021 (4)0.0202 (5)
O20.0498 (5)0.0525 (6)0.0734 (7)0.0106 (4)0.0037 (5)0.0184 (5)
O30.0342 (5)0.0622 (6)0.0722 (7)0.0043 (4)0.0006 (4)0.0204 (5)
C10.0333 (6)0.0489 (7)0.0522 (7)0.0028 (5)0.0011 (5)0.0034 (5)
C20.0319 (6)0.0539 (8)0.0604 (8)0.0037 (5)0.0028 (5)0.0047 (6)
C30.0420 (6)0.0411 (6)0.0440 (6)0.0049 (5)0.0015 (5)0.0001 (5)
C40.0378 (6)0.0530 (8)0.0560 (7)0.0002 (5)0.0055 (5)0.0094 (6)
C50.0324 (6)0.0571 (8)0.0595 (8)0.0049 (5)0.0000 (5)0.0097 (6)
C60.0356 (6)0.0429 (6)0.0419 (6)0.0009 (5)0.0030 (5)0.0017 (5)
C70.0370 (6)0.0447 (7)0.0470 (6)0.0012 (5)0.0013 (5)0.0016 (5)
C80.0375 (6)0.0548 (8)0.0589 (7)0.0006 (5)0.0010 (6)0.0156 (6)
C90.0372 (6)0.0436 (7)0.0467 (6)0.0005 (5)0.0014 (5)0.0041 (5)
C100.0357 (6)0.0387 (6)0.0421 (6)0.0020 (5)0.0016 (5)0.0019 (5)
C110.0408 (6)0.0423 (6)0.0469 (6)0.0023 (5)0.0030 (5)0.0106 (5)
C120.0360 (6)0.0470 (7)0.0550 (7)0.0019 (5)0.0059 (5)0.0100 (5)
C130.0341 (6)0.0442 (6)0.0444 (6)0.0048 (5)0.0027 (5)0.0006 (5)
C140.0406 (6)0.0405 (6)0.0481 (6)0.0043 (5)0.0031 (5)0.0089 (5)
C150.0369 (6)0.0419 (6)0.0535 (7)0.0021 (5)0.0038 (5)0.0094 (5)
C160.0672 (10)0.0531 (8)0.0835 (11)0.0098 (7)0.0132 (8)0.0220 (8)
Geometric parameters (Å, º) top
O1—C91.2311 (15)C7—H70.93
O2—C31.3624 (15)C8—C91.4707 (18)
O2—C161.4199 (18)C8—H80.93
O3—C131.3511 (14)C9—C101.4772 (16)
O3—H30.82C10—C151.3952 (17)
C1—C21.3750 (18)C10—C111.3974 (16)
C1—C61.3959 (16)C11—C121.3753 (17)
C1—H10.93C11—H110.93
C2—C31.3863 (18)C12—C131.3850 (17)
C2—H20.93C12—H120.93
C3—C41.3822 (17)C13—C141.3882 (17)
C4—C51.3773 (19)C14—C151.3779 (17)
C4—H40.93C14—H140.93
C5—C61.3913 (17)C15—H150.93
C5—H50.93C16—H16A0.96
C6—C71.4592 (17)C16—H16B0.96
C7—C81.3194 (18)C16—H16C0.96
C3—O2—C16118.32 (11)O1—C9—C10121.72 (11)
C13—O3—H3109.5C8—C9—C10118.65 (11)
C2—C1—C6121.56 (12)C15—C10—C11117.27 (11)
C2—C1—H1119.2C15—C10—C9120.04 (11)
C6—C1—H1119.2C11—C10—C9122.68 (11)
C1—C2—C3120.00 (11)C12—C11—C10121.62 (11)
C1—C2—H2120.0C12—C11—H11119.2
C3—C2—H2120.0C10—C11—H11119.2
O2—C3—C4124.08 (12)C11—C12—C13119.97 (11)
O2—C3—C2116.13 (11)C11—C12—H12120.0
C4—C3—C2119.79 (12)C13—C12—H12120.0
C5—C4—C3119.43 (12)O3—C13—C12117.55 (11)
C5—C4—H4120.3O3—C13—C14122.77 (11)
C3—C4—H4120.3C12—C13—C14119.67 (11)
C4—C5—C6122.24 (12)C15—C14—C13119.80 (11)
C4—C5—H5118.9C15—C14—H14120.1
C6—C5—H5118.9C13—C14—H14120.1
C5—C6—C1116.98 (11)C14—C15—C10121.65 (11)
C5—C6—C7122.78 (11)C14—C15—H15119.2
C1—C6—C7120.24 (11)C10—C15—H15119.2
C8—C7—C6126.11 (12)O2—C16—H16A109.5
C8—C7—H7116.9O2—C16—H16B109.5
C6—C7—H7116.9H16A—C16—H16B109.5
C7—C8—C9123.40 (12)O2—C16—H16C109.5
C7—C8—H8118.3H16A—C16—H16C109.5
C9—C8—H8118.3H16B—C16—H16C109.5
O1—C9—C8119.62 (11)
C6—C1—C2—C30.1 (2)C7—C8—C9—C10174.34 (13)
C16—O2—C3—C44.7 (2)O1—C9—C10—C151.6 (2)
C16—O2—C3—C2175.46 (14)C8—C9—C10—C15178.10 (12)
C1—C2—C3—O2179.61 (12)O1—C9—C10—C11179.40 (13)
C1—C2—C3—C40.3 (2)C8—C9—C10—C110.88 (19)
O2—C3—C4—C5179.54 (13)C15—C10—C11—C120.42 (19)
C2—C3—C4—C50.3 (2)C9—C10—C11—C12178.59 (12)
C3—C4—C5—C60.0 (2)C10—C11—C12—C130.2 (2)
C4—C5—C6—C10.4 (2)C11—C12—C13—O3178.32 (12)
C4—C5—C6—C7179.13 (12)C11—C12—C13—C140.8 (2)
C2—C1—C6—C50.48 (19)O3—C13—C14—C15178.30 (12)
C2—C1—C6—C7179.09 (12)C12—C13—C14—C150.8 (2)
C5—C6—C7—C82.8 (2)C13—C14—C15—C100.1 (2)
C1—C6—C7—C8176.71 (13)C11—C10—C15—C140.45 (19)
C6—C7—C8—C9179.96 (12)C9—C10—C15—C14178.59 (12)
C7—C8—C9—O15.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1i0.821.882.688 (2)169
C1—H1···O2ii0.932.863.674 (2)147
C4—H4···O3iii0.932.723.393 (2)130
C7—H7···O10.932.502.808 (2)100
C7—H7···O2ii0.932.533.425 (2)162
C14—H14···O1i0.932.933.547 (2)125
C14—H14···O2iv0.932.633.455 (2)149
C15—H15···O10.932.542.828 (2)99
C15—H15···O3v0.932.603.490 (2)162
C16—H16A···O1vi0.962.823.344 (2)116
C16—H16C···O3iii0.962.683.548 (2)151
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y1/2, z+1/2; (iv) x+1/2, y+1, z1/2; (v) x+1/2, y+3/2, z; (vi) x, y+1/2, z+1/2.
 

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