The title molecule, C
16H
14O
3, 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),

(6) and

(7).
Supporting information
CCDC reference: 264093
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(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
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
C16H14O3 | F(000) = 1072 |
Mr = 254.27 | Dx = 1.317 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 6162 reflections |
a = 13.4346 (8) Å | θ = 4.9–54.7° |
b = 11.4998 (7) Å | µ = 0.09 mm−1 |
c = 16.6055 (10) Å | T = 293 K |
V = 2565.5 (3) Å3 | Block, colourless |
Z = 8 | 0.59 × 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 tube | Rint = 0.023 |
Graphite monochromator | θmax = 28.3°, θmin = 2.5° |
ω scans | h = −16→17 |
15000 measured reflections | k = −10→15 |
3015 independent reflections | l = −21→22 |
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)] = 0.044 | H-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 reflections | Δρmax = 0.19 e Å−3 |
175 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXTL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.29376 (7) | 0.63939 (9) | 0.08155 (6) | 0.0562 (3) | |
O2 | 0.43974 (7) | 0.06151 (9) | 0.36966 (6) | 0.0586 (3) | |
O3 | −0.17087 (6) | 0.67671 (9) | 0.01419 (7) | 0.0562 (3) | |
H3 | −0.1735 | 0.7338 | −0.0153 | 0.084* | |
C1 | 0.45688 (9) | 0.31078 (11) | 0.23901 (8) | 0.0448 (3) | |
H1 | 0.5070 | 0.3530 | 0.2138 | 0.054* | |
C2 | 0.48204 (9) | 0.21708 (12) | 0.28625 (8) | 0.0487 (3) | |
H2 | 0.5485 | 0.1965 | 0.2926 | 0.058* | |
C3 | 0.40830 (9) | 0.15332 (11) | 0.32447 (7) | 0.0424 (3) | |
C4 | 0.30962 (9) | 0.18459 (12) | 0.31520 (8) | 0.0489 (3) | |
H4 | 0.2598 | 0.1425 | 0.3409 | 0.059* | |
C5 | 0.28576 (9) | 0.27863 (12) | 0.26760 (8) | 0.0497 (3) | |
H5 | 0.2192 | 0.2991 | 0.2617 | 0.060* | |
C6 | 0.35787 (9) | 0.34405 (10) | 0.22805 (7) | 0.0401 (3) | |
C7 | 0.33350 (9) | 0.44287 (11) | 0.17658 (7) | 0.0429 (3) | |
H7 | 0.3866 | 0.4838 | 0.1545 | 0.051* | |
C8 | 0.24320 (10) | 0.47962 (12) | 0.15846 (8) | 0.0504 (3) | |
H8 | 0.1891 | 0.4399 | 0.1800 | 0.060* | |
C9 | 0.22370 (9) | 0.58009 (11) | 0.10598 (8) | 0.0425 (3) | |
C10 | 0.11971 (8) | 0.60669 (10) | 0.08370 (7) | 0.0388 (3) | |
C11 | 0.03902 (9) | 0.54121 (11) | 0.11133 (7) | 0.0433 (3) | |
H11 | 0.0505 | 0.4792 | 0.1461 | 0.052* | |
C12 | −0.05700 (9) | 0.56614 (11) | 0.08838 (8) | 0.0460 (3) | |
H12 | −0.1095 | 0.5214 | 0.1077 | 0.055* | |
C13 | −0.07549 (9) | 0.65788 (10) | 0.03645 (7) | 0.0409 (3) | |
C14 | 0.00312 (9) | 0.72515 (11) | 0.00864 (8) | 0.0431 (3) | |
H14 | −0.0089 | 0.7875 | −0.0257 | 0.052* | |
C15 | 0.09898 (9) | 0.69932 (11) | 0.03210 (8) | 0.0441 (3) | |
H15 | 0.1512 | 0.7448 | 0.0131 | 0.053* | |
C16 | 0.36787 (13) | −0.00137 (14) | 0.41476 (11) | 0.0679 (4) | |
H16A | 0.4007 | −0.0594 | 0.4467 | 0.102* | |
H16B | 0.3219 | −0.0383 | 0.3786 | 0.102* | |
H16C | 0.3325 | 0.0511 | 0.4494 | 0.102* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0375 (5) | 0.0584 (6) | 0.0726 (7) | −0.0033 (4) | 0.0021 (4) | 0.0202 (5) |
O2 | 0.0498 (5) | 0.0525 (6) | 0.0734 (7) | 0.0106 (4) | 0.0037 (5) | 0.0184 (5) |
O3 | 0.0342 (5) | 0.0622 (6) | 0.0722 (7) | 0.0043 (4) | −0.0006 (4) | 0.0204 (5) |
C1 | 0.0333 (6) | 0.0489 (7) | 0.0522 (7) | −0.0028 (5) | −0.0011 (5) | 0.0034 (5) |
C2 | 0.0319 (6) | 0.0539 (8) | 0.0604 (8) | 0.0037 (5) | −0.0028 (5) | 0.0047 (6) |
C3 | 0.0420 (6) | 0.0411 (6) | 0.0440 (6) | 0.0049 (5) | −0.0015 (5) | −0.0001 (5) |
C4 | 0.0378 (6) | 0.0530 (8) | 0.0560 (7) | −0.0002 (5) | 0.0055 (5) | 0.0094 (6) |
C5 | 0.0324 (6) | 0.0571 (8) | 0.0595 (8) | 0.0049 (5) | 0.0000 (5) | 0.0097 (6) |
C6 | 0.0356 (6) | 0.0429 (6) | 0.0419 (6) | 0.0009 (5) | −0.0030 (5) | −0.0017 (5) |
C7 | 0.0370 (6) | 0.0447 (7) | 0.0470 (6) | −0.0012 (5) | −0.0013 (5) | 0.0016 (5) |
C8 | 0.0375 (6) | 0.0548 (8) | 0.0589 (7) | −0.0006 (5) | −0.0010 (6) | 0.0156 (6) |
C9 | 0.0372 (6) | 0.0436 (7) | 0.0467 (6) | 0.0005 (5) | 0.0014 (5) | 0.0041 (5) |
C10 | 0.0357 (6) | 0.0387 (6) | 0.0421 (6) | 0.0020 (5) | 0.0016 (5) | 0.0019 (5) |
C11 | 0.0408 (6) | 0.0423 (6) | 0.0469 (6) | 0.0023 (5) | 0.0030 (5) | 0.0106 (5) |
C12 | 0.0360 (6) | 0.0470 (7) | 0.0550 (7) | −0.0019 (5) | 0.0059 (5) | 0.0100 (5) |
C13 | 0.0341 (6) | 0.0442 (6) | 0.0444 (6) | 0.0048 (5) | 0.0027 (5) | 0.0006 (5) |
C14 | 0.0406 (6) | 0.0405 (6) | 0.0481 (6) | 0.0043 (5) | 0.0031 (5) | 0.0089 (5) |
C15 | 0.0369 (6) | 0.0419 (6) | 0.0535 (7) | −0.0021 (5) | 0.0038 (5) | 0.0094 (5) |
C16 | 0.0672 (10) | 0.0531 (8) | 0.0835 (11) | 0.0098 (7) | 0.0132 (8) | 0.0220 (8) |
Geometric parameters (Å, º) top
O1—C9 | 1.2311 (15) | C7—H7 | 0.93 |
O2—C3 | 1.3624 (15) | C8—C9 | 1.4707 (18) |
O2—C16 | 1.4199 (18) | C8—H8 | 0.93 |
O3—C13 | 1.3511 (14) | C9—C10 | 1.4772 (16) |
O3—H3 | 0.82 | C10—C15 | 1.3952 (17) |
C1—C2 | 1.3750 (18) | C10—C11 | 1.3974 (16) |
C1—C6 | 1.3959 (16) | C11—C12 | 1.3753 (17) |
C1—H1 | 0.93 | C11—H11 | 0.93 |
C2—C3 | 1.3863 (18) | C12—C13 | 1.3850 (17) |
C2—H2 | 0.93 | C12—H12 | 0.93 |
C3—C4 | 1.3822 (17) | C13—C14 | 1.3882 (17) |
C4—C5 | 1.3773 (19) | C14—C15 | 1.3779 (17) |
C4—H4 | 0.93 | C14—H14 | 0.93 |
C5—C6 | 1.3913 (17) | C15—H15 | 0.93 |
C5—H5 | 0.93 | C16—H16A | 0.96 |
C6—C7 | 1.4592 (17) | C16—H16B | 0.96 |
C7—C8 | 1.3194 (18) | C16—H16C | 0.96 |
| | | |
C3—O2—C16 | 118.32 (11) | O1—C9—C10 | 121.72 (11) |
C13—O3—H3 | 109.5 | C8—C9—C10 | 118.65 (11) |
C2—C1—C6 | 121.56 (12) | C15—C10—C11 | 117.27 (11) |
C2—C1—H1 | 119.2 | C15—C10—C9 | 120.04 (11) |
C6—C1—H1 | 119.2 | C11—C10—C9 | 122.68 (11) |
C1—C2—C3 | 120.00 (11) | C12—C11—C10 | 121.62 (11) |
C1—C2—H2 | 120.0 | C12—C11—H11 | 119.2 |
C3—C2—H2 | 120.0 | C10—C11—H11 | 119.2 |
O2—C3—C4 | 124.08 (12) | C11—C12—C13 | 119.97 (11) |
O2—C3—C2 | 116.13 (11) | C11—C12—H12 | 120.0 |
C4—C3—C2 | 119.79 (12) | C13—C12—H12 | 120.0 |
C5—C4—C3 | 119.43 (12) | O3—C13—C12 | 117.55 (11) |
C5—C4—H4 | 120.3 | O3—C13—C14 | 122.77 (11) |
C3—C4—H4 | 120.3 | C12—C13—C14 | 119.67 (11) |
C4—C5—C6 | 122.24 (12) | C15—C14—C13 | 119.80 (11) |
C4—C5—H5 | 118.9 | C15—C14—H14 | 120.1 |
C6—C5—H5 | 118.9 | C13—C14—H14 | 120.1 |
C5—C6—C1 | 116.98 (11) | C14—C15—C10 | 121.65 (11) |
C5—C6—C7 | 122.78 (11) | C14—C15—H15 | 119.2 |
C1—C6—C7 | 120.24 (11) | C10—C15—H15 | 119.2 |
C8—C7—C6 | 126.11 (12) | O2—C16—H16A | 109.5 |
C8—C7—H7 | 116.9 | O2—C16—H16B | 109.5 |
C6—C7—H7 | 116.9 | H16A—C16—H16B | 109.5 |
C7—C8—C9 | 123.40 (12) | O2—C16—H16C | 109.5 |
C7—C8—H8 | 118.3 | H16A—C16—H16C | 109.5 |
C9—C8—H8 | 118.3 | H16B—C16—H16C | 109.5 |
O1—C9—C8 | 119.62 (11) | | |
| | | |
C6—C1—C2—C3 | −0.1 (2) | C7—C8—C9—C10 | 174.34 (13) |
C16—O2—C3—C4 | −4.7 (2) | O1—C9—C10—C15 | 1.6 (2) |
C16—O2—C3—C2 | 175.46 (14) | C8—C9—C10—C15 | −178.10 (12) |
C1—C2—C3—O2 | 179.61 (12) | O1—C9—C10—C11 | −179.40 (13) |
C1—C2—C3—C4 | −0.3 (2) | C8—C9—C10—C11 | 0.88 (19) |
O2—C3—C4—C5 | −179.54 (13) | C15—C10—C11—C12 | 0.42 (19) |
C2—C3—C4—C5 | 0.3 (2) | C9—C10—C11—C12 | −178.59 (12) |
C3—C4—C5—C6 | 0.0 (2) | C10—C11—C12—C13 | 0.2 (2) |
C4—C5—C6—C1 | −0.4 (2) | C11—C12—C13—O3 | 178.32 (12) |
C4—C5—C6—C7 | 179.13 (12) | C11—C12—C13—C14 | −0.8 (2) |
C2—C1—C6—C5 | 0.48 (19) | O3—C13—C14—C15 | −178.30 (12) |
C2—C1—C6—C7 | −179.09 (12) | C12—C13—C14—C15 | 0.8 (2) |
C5—C6—C7—C8 | −2.8 (2) | C13—C14—C15—C10 | −0.1 (2) |
C1—C6—C7—C8 | 176.71 (13) | C11—C10—C15—C14 | −0.45 (19) |
C6—C7—C8—C9 | −179.96 (12) | C9—C10—C15—C14 | 178.59 (12) |
C7—C8—C9—O1 | −5.4 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1i | 0.82 | 1.88 | 2.688 (2) | 169 |
C1—H1···O2ii | 0.93 | 2.86 | 3.674 (2) | 147 |
C4—H4···O3iii | 0.93 | 2.72 | 3.393 (2) | 130 |
C7—H7···O1 | 0.93 | 2.50 | 2.808 (2) | 100 |
C7—H7···O2ii | 0.93 | 2.53 | 3.425 (2) | 162 |
C14—H14···O1i | 0.93 | 2.93 | 3.547 (2) | 125 |
C14—H14···O2iv | 0.93 | 2.63 | 3.455 (2) | 149 |
C15—H15···O1 | 0.93 | 2.54 | 2.828 (2) | 99 |
C15—H15···O3v | 0.93 | 2.60 | 3.490 (2) | 162 |
C16—H16A···O1vi | 0.96 | 2.82 | 3.344 (2) | 116 |
C16—H16C···O3iii | 0.96 | 2.68 | 3.548 (2) | 151 |
Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x+1/2, −y+1, z−1/2; (v) x+1/2, −y+3/2, −z; (vi) x, −y+1/2, z+1/2. |