organic compounds
7-Methoxy-2-phenylchroman-4-one
aFaculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Krakow, Poland
*Correspondence e-mail: agata.piaskowska@uj.edu.pl
In the title compound, C16H14O3, the ring O atom and the two adjacent non-fused C atoms, as well as the attached phenyl ring, exhibit static disorder [occupancy ratio 0.559 (12):0.441 (12)]. The crystal packing features π–π [centroid–centroid distance = 3.912 (1) Å] and C—H⋯π interactions.
Related literature
For aromatase inhibition of flavanones, see: Hong & Chen (2006). For the properties of 7-methoxyflavanone, see: Pouget et al. (2001); Le Bail et al. (1998); Kostrzewa-Susłow et al. (2010). For classification of X—H⋯π interactions, see: Malone et al. (1997).
Experimental
Crystal data
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Refinement
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Data collection: COLLECT (Nonius, 1998); cell SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536813001451/kj2213sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813001451/kj2213Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813001451/kj2213Isup3.cml
The title compound was purchased from Sigma-Aldrich and used without further purification. Single crystals were obtained by slow evaporation of MeOH solution.
All hydrogen atom positions were observed in difference Fourier map. Nevertheless, in the
procedure the hydrogen atoms were positioned geometrically and refined using a riding model (including about the C—C bond for CH3groups), with C—H = 0.93—0.96 Å (C—H = 0.97 Å for CH2 groups, 0.96 Å for CH3 groups, and 0.93 Å for aromatic CH) and with Uiso(H) = 1.5Ueq(C) for methyl groups and Uiso(H) = 1.2Ueq(C) for all other H atoms. Disordered non-H atoms were refined with isotropic displacement parameters.Data collection: COLLECT (Nonius, 1998); cell
SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. ORTEP-3 (Farrugia, 2012) drawing of the title compound with labels. Displacement ellipsoids of non-H atoms drawn at 30% probabilty level. | |
Fig. 2. C—H···π and interactions in the crystal packing. Thermal ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) -x, y-½, ½-z, (ii) -x, y+½, ½-z, (iii) 1 - x, 1 - y, -z.] | |
Fig. 3. π–π interactions in the crystal packing. Thermal ellipsoids are drawn at the 30% probability level. [Symmetry codes: (iv) 1 - x, -y, -z, (v) 2 - x, -y, -z, (vi) x + 1, y, z.] |
C16H14O3 | F(000) = 536 |
Mr = 254.27 | Dx = 1.271 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 13054 reflections |
a = 8.5600 (3) Å | θ = 0.4–26.4° |
b = 6.6320 (2) Å | µ = 0.09 mm−1 |
c = 23.4130 (7) Å | T = 293 K |
β = 90.742 (2)° | Prism, colourless |
V = 1329.04 (7) Å3 | 0.55 × 0.16 × 0.10 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 2710 independent reflections |
Radiation source: fine-focus sealed tube | 1765 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.072 |
Detector resolution: 9 pixels mm-1 | θmax = 26.4°, θmin = 2.9° |
CCD scans | h = −8→10 |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | k = −8→8 |
Tmin = 0.954, Tmax = 0.991 | l = −29→29 |
15170 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.086 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.280 | H-atom parameters constrained |
S = 1.18 | w = 1/[σ2(Fo2) + (0.1433P)2 + 0.4478P] where P = (Fo2 + 2Fc2)/3 |
2710 reflections | (Δ/σ)max < 0.001 |
165 parameters | Δρmax = 0.65 e Å−3 |
122 restraints | Δρmin = −0.35 e Å−3 |
C16H14O3 | V = 1329.04 (7) Å3 |
Mr = 254.27 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.5600 (3) Å | µ = 0.09 mm−1 |
b = 6.6320 (2) Å | T = 293 K |
c = 23.4130 (7) Å | 0.55 × 0.16 × 0.10 mm |
β = 90.742 (2)° |
Nonius KappaCCD diffractometer | 2710 independent reflections |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | 1765 reflections with I > 2σ(I) |
Tmin = 0.954, Tmax = 0.991 | Rint = 0.072 |
15170 measured reflections |
R[F2 > 2σ(F2)] = 0.086 | 122 restraints |
wR(F2) = 0.280 | H-atom parameters constrained |
S = 1.18 | Δρmax = 0.65 e Å−3 |
2710 reflections | Δρmin = −0.35 e Å−3 |
165 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O17 | 0.5477 (4) | −0.2944 (5) | 0.18360 (14) | 0.0728 (11) | |
O18 | 0.8157 (4) | 0.1840 (5) | −0.02843 (13) | 0.0638 (9) | |
C4 | 0.5036 (5) | −0.1399 (6) | 0.15982 (17) | 0.0534 (11) | |
C5 | 0.5802 (5) | −0.0580 (6) | 0.10887 (16) | 0.0476 (10) | |
C6 | 0.7077 (5) | −0.1537 (7) | 0.08388 (19) | 0.0592 (12) | |
H6 | 0.7426 | −0.2759 | 0.0988 | 0.071* | |
C7 | 0.7821 (5) | −0.0726 (7) | 0.03831 (18) | 0.0577 (12) | |
H7 | 0.8668 | −0.1386 | 0.0224 | 0.069* | |
C8 | 0.7298 (5) | 0.1117 (6) | 0.01556 (16) | 0.0483 (10) | |
C9 | 0.6034 (5) | 0.2073 (6) | 0.03813 (16) | 0.0483 (10) | |
H9 | 0.5684 | 0.3286 | 0.0227 | 0.058* | |
C10 | 0.5271 (4) | 0.1219 (6) | 0.08444 (15) | 0.0429 (9) | |
C19 | 0.7766 (7) | 0.3789 (8) | −0.0506 (2) | 0.0777 (16) | |
H19A | 0.6695 | 0.3793 | −0.0634 | 0.116* | |
H19B | 0.8431 | 0.4098 | −0.0822 | 0.116* | |
H19C | 0.7908 | 0.4784 | −0.0213 | 0.116* | |
O1A | 0.4127 (8) | 0.2362 (10) | 0.1081 (3) | 0.043 (2)* | 0.559 (12) |
C2A | 0.3587 (8) | 0.1876 (10) | 0.1623 (3) | 0.043 (2)* | 0.559 (12) |
H2A | 0.4289 | 0.2677 | 0.1867 | 0.052* | 0.559 (12) |
C3A | 0.3801 (12) | −0.0050 (14) | 0.1850 (4) | 0.049 (3)* | 0.559 (12) |
H3A1 | 0.2810 | −0.0754 | 0.1819 | 0.059* | 0.559 (12) |
H3A2 | 0.4039 | 0.0100 | 0.2254 | 0.059* | 0.559 (12) |
C11A | 0.2053 (10) | 0.2932 (13) | 0.1710 (4) | 0.047 (2)* | 0.559 (12) |
C12A | 0.2038 (13) | 0.4478 (18) | 0.2065 (6) | 0.065 (4)* | 0.559 (12) |
H12A | 0.2961 | 0.4805 | 0.2258 | 0.078* | 0.559 (12) |
C13A | 0.0813 (12) | 0.5567 (15) | 0.2160 (4) | 0.062 (3)* | 0.559 (12) |
H13A | 0.0901 | 0.6657 | 0.2408 | 0.074* | 0.559 (12) |
C14A | −0.0591 (11) | 0.5178 (13) | 0.1912 (4) | 0.050 (2)* | 0.559 (12) |
H14A | −0.1453 | 0.5977 | 0.1992 | 0.060* | 0.559 (12) |
C15A | −0.0727 (12) | 0.3545 (19) | 0.1530 (5) | 0.068 (4)* | 0.559 (12) |
H15A | −0.1678 | 0.3222 | 0.1356 | 0.082* | 0.559 (12) |
C16A | 0.0671 (13) | 0.2391 (16) | 0.1419 (5) | 0.061 (3)* | 0.559 (12) |
H16A | 0.0655 | 0.1322 | 0.1162 | 0.073* | 0.559 (12) |
O1B | 0.3856 (10) | 0.2064 (12) | 0.0994 (3) | 0.036 (2)* | 0.441 (12) |
C2B | 0.2931 (11) | 0.1055 (15) | 0.1386 (4) | 0.050 (3)* | 0.441 (12) |
H2B | 0.2276 | 0.0244 | 0.1128 | 0.060* | 0.441 (12) |
C3B | 0.3513 (14) | −0.0439 (19) | 0.1748 (5) | 0.046 (3)* | 0.441 (12) |
H3B1 | 0.2734 | −0.1497 | 0.1770 | 0.055* | 0.441 (12) |
H3B2 | 0.3624 | 0.0137 | 0.2127 | 0.055* | 0.441 (12) |
C11B | 0.1728 (13) | 0.2564 (14) | 0.1603 (4) | 0.040 (3)* | 0.441 (12) |
C12B | 0.1843 (14) | 0.424 (2) | 0.1974 (7) | 0.062 (5)* | 0.441 (12) |
H12B | 0.2792 | 0.4617 | 0.2140 | 0.074* | 0.441 (12) |
C13B | 0.0404 (14) | 0.5362 (17) | 0.2086 (5) | 0.052 (3)* | 0.441 (12) |
H13B | 0.0393 | 0.6463 | 0.2333 | 0.062* | 0.441 (12) |
C14B | −0.0916 (11) | 0.4712 (16) | 0.1813 (4) | 0.044 (3)* | 0.441 (12) |
H14B | −0.1852 | 0.5388 | 0.1871 | 0.053* | 0.441 (12) |
C15B | −0.0895 (15) | 0.313 (2) | 0.1463 (7) | 0.068 (5)* | 0.441 (12) |
H15B | −0.1818 | 0.2747 | 0.1280 | 0.082* | 0.441 (12) |
C16B | 0.0329 (14) | 0.213 (2) | 0.1373 (6) | 0.063 (5)* | 0.441 (12) |
H16B | 0.0256 | 0.1026 | 0.1130 | 0.076* | 0.441 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O17 | 0.072 (2) | 0.069 (2) | 0.078 (2) | 0.0210 (17) | 0.0127 (17) | 0.0313 (17) |
O18 | 0.065 (2) | 0.063 (2) | 0.0643 (18) | 0.0106 (15) | 0.0277 (15) | 0.0115 (14) |
C4 | 0.054 (3) | 0.053 (2) | 0.053 (2) | 0.004 (2) | 0.0016 (19) | 0.0095 (19) |
C5 | 0.045 (2) | 0.048 (2) | 0.050 (2) | 0.0077 (18) | 0.0035 (17) | 0.0043 (17) |
C6 | 0.058 (3) | 0.053 (2) | 0.066 (3) | 0.015 (2) | 0.007 (2) | 0.011 (2) |
C7 | 0.052 (3) | 0.059 (3) | 0.063 (3) | 0.015 (2) | 0.017 (2) | 0.003 (2) |
C8 | 0.045 (2) | 0.053 (2) | 0.047 (2) | 0.0039 (18) | 0.0085 (17) | 0.0032 (17) |
C9 | 0.050 (2) | 0.046 (2) | 0.049 (2) | 0.0081 (18) | 0.0058 (18) | 0.0056 (16) |
C10 | 0.041 (2) | 0.046 (2) | 0.0426 (19) | 0.0041 (16) | 0.0048 (16) | −0.0013 (16) |
C19 | 0.095 (4) | 0.065 (3) | 0.074 (3) | 0.008 (3) | 0.036 (3) | 0.016 (2) |
O17—C4 | 1.224 (5) | C11A—C16A | 1.404 (12) |
O18—C8 | 1.361 (5) | C12A—C13A | 1.295 (11) |
O18—C19 | 1.432 (6) | C12A—H12A | 0.9300 |
C4—C5 | 1.472 (6) | C13A—C14A | 1.353 (11) |
C4—C3B | 1.496 (12) | C13A—H13A | 0.9300 |
C4—C3A | 1.510 (10) | C14A—C15A | 1.409 (12) |
C5—C10 | 1.397 (5) | C14A—H14A | 0.9300 |
C5—C6 | 1.398 (6) | C15A—C16A | 1.447 (12) |
C6—C7 | 1.360 (6) | C15A—H15A | 0.9300 |
C6—H6 | 0.9300 | C16A—H16A | 0.9300 |
C7—C8 | 1.404 (6) | O1B—C2B | 1.392 (11) |
C7—H7 | 0.9300 | C2B—C3B | 1.391 (14) |
C8—C9 | 1.366 (5) | C2B—C11B | 1.527 (13) |
C9—C10 | 1.393 (5) | C2B—H2B | 0.9800 |
C9—H9 | 0.9300 | C3B—H3B1 | 0.9700 |
C10—O1A | 1.362 (7) | C3B—H3B2 | 0.9700 |
C10—O1B | 1.384 (8) | C11B—C16B | 1.337 (13) |
C19—H19A | 0.9600 | C11B—C12B | 1.414 (13) |
C19—H19B | 0.9600 | C12B—C13B | 1.465 (13) |
C19—H19C | 0.9600 | C12B—H12B | 0.9300 |
O1A—C2A | 1.394 (9) | C13B—C14B | 1.362 (13) |
C2A—C3A | 1.395 (11) | C13B—H13B | 0.9300 |
C2A—C11A | 1.504 (10) | C14B—C15B | 1.330 (13) |
C2A—H2A | 0.9800 | C14B—H14B | 0.9300 |
C3A—H3A1 | 0.9700 | C15B—C16B | 1.260 (13) |
C3A—H3A2 | 0.9700 | C15B—H15B | 0.9300 |
C11A—C12A | 1.321 (12) | C16B—H16B | 0.9300 |
C8—O18—C19 | 117.8 (3) | C12A—C11A—C2A | 117.5 (8) |
O17—C4—C5 | 122.6 (4) | C16A—C11A—C2A | 123.2 (8) |
O17—C4—C3B | 121.0 (5) | C13A—C12A—C11A | 123.8 (10) |
C5—C4—C3B | 115.5 (5) | C13A—C12A—H12A | 118.1 |
O17—C4—C3A | 122.1 (5) | C11A—C12A—H12A | 118.1 |
C5—C4—C3A | 114.8 (5) | C12A—C13A—C14A | 122.4 (9) |
C3B—C4—C3A | 16.3 (6) | C12A—C13A—H13A | 118.8 |
C10—C5—C6 | 117.9 (4) | C14A—C13A—H13A | 118.8 |
C10—C5—C4 | 120.1 (3) | C13A—C14A—C15A | 119.0 (7) |
C6—C5—C4 | 122.0 (4) | C13A—C14A—H14A | 120.5 |
C7—C6—C5 | 121.6 (4) | C15A—C14A—H14A | 120.5 |
C7—C6—H6 | 119.2 | C14A—C15A—C16A | 117.3 (8) |
C5—C6—H6 | 119.2 | C14A—C15A—H15A | 121.4 |
C6—C7—C8 | 119.4 (4) | C16A—C15A—H15A | 121.4 |
C6—C7—H7 | 120.3 | C11A—C16A—C15A | 118.1 (8) |
C8—C7—H7 | 120.3 | C11A—C16A—H16A | 120.9 |
O18—C8—C9 | 124.6 (4) | C15A—C16A—H16A | 120.9 |
O18—C8—C7 | 114.9 (3) | C10—O1B—C2B | 118.7 (6) |
C9—C8—C7 | 120.5 (4) | C3B—C2B—O1B | 122.8 (9) |
C8—C9—C10 | 119.6 (4) | C3B—C2B—C11B | 120.2 (8) |
C8—C9—H9 | 120.2 | O1B—C2B—C11B | 107.2 (7) |
C10—C9—H9 | 120.2 | C3B—C2B—H2B | 100.5 |
O1A—C10—O1B | 15.2 (4) | O1B—C2B—H2B | 100.5 |
O1A—C10—C9 | 115.9 (4) | C11B—C2B—H2B | 100.5 |
O1B—C10—C9 | 116.9 (4) | C2B—C3B—C4 | 117.9 (8) |
O1A—C10—C5 | 122.8 (4) | C2B—C3B—H3B1 | 107.8 |
O1B—C10—C5 | 121.6 (4) | C4—C3B—H3B1 | 107.8 |
C9—C10—C5 | 120.9 (3) | C2B—C3B—H3B2 | 107.8 |
O18—C19—H19A | 109.5 | C4—C3B—H3B2 | 107.8 |
O18—C19—H19B | 109.5 | H3B1—C3B—H3B2 | 107.2 |
H19A—C19—H19B | 109.5 | C16B—C11B—C12B | 118.0 (8) |
O18—C19—H19C | 109.5 | C16B—C11B—C2B | 109.3 (9) |
H19A—C19—H19C | 109.5 | C12B—C11B—C2B | 132.7 (10) |
H19B—C19—H19C | 109.5 | C11B—C12B—C13B | 117.3 (9) |
C10—O1A—C2A | 119.3 (5) | C11B—C12B—H12B | 121.4 |
O1A—C2A—C3A | 121.0 (6) | C13B—C12B—H12B | 121.4 |
O1A—C2A—C11A | 108.4 (6) | C14B—C13B—C12B | 116.6 (9) |
C3A—C2A—C11A | 119.0 (7) | C14B—C13B—H13B | 121.7 |
O1A—C2A—H2A | 101.4 | C12B—C13B—H13B | 121.7 |
C3A—C2A—H2A | 101.4 | C15B—C14B—C13B | 121.5 (9) |
C11A—C2A—H2A | 101.4 | C15B—C14B—H14B | 119.3 |
C2A—C3A—C4 | 118.9 (7) | C13B—C14B—H14B | 119.3 |
C2A—C3A—H3A1 | 107.6 | C16B—C15B—C14B | 122.3 (11) |
C4—C3A—H3A1 | 107.6 | C16B—C15B—H15B | 118.8 |
C2A—C3A—H3A2 | 107.6 | C14B—C15B—H15B | 118.8 |
C4—C3A—H3A2 | 107.6 | C15B—C16B—C11B | 124.3 (11) |
H3A1—C3A—H3A2 | 107.0 | C15B—C16B—H16B | 117.9 |
C12A—C11A—C16A | 119.3 (8) | C11B—C16B—H16B | 117.9 |
O17—C4—C5—C10 | −178.3 (4) | O1A—C2A—C11A—C12A | −107.5 (10) |
C3B—C4—C5—C10 | 12.2 (8) | C3A—C2A—C11A—C12A | 108.8 (11) |
C3A—C4—C5—C10 | −5.9 (7) | O1A—C2A—C11A—C16A | 70.2 (10) |
O17—C4—C5—C6 | 0.8 (7) | C3A—C2A—C11A—C16A | −73.4 (12) |
C3B—C4—C5—C6 | −168.7 (7) | C16A—C11A—C12A—C13A | −0.8 (19) |
C3A—C4—C5—C6 | 173.3 (6) | C2A—C11A—C12A—C13A | 177.1 (11) |
C10—C5—C6—C7 | 2.1 (7) | C11A—C12A—C13A—C14A | 2 (2) |
C4—C5—C6—C7 | −177.1 (4) | C12A—C13A—C14A—C15A | −0.8 (16) |
C5—C6—C7—C8 | −0.1 (7) | C13A—C14A—C15A—C16A | −1.0 (16) |
C19—O18—C8—C9 | 3.7 (6) | C12A—C11A—C16A—C15A | −1.0 (16) |
C19—O18—C8—C7 | −175.1 (4) | C2A—C11A—C16A—C15A | −178.8 (9) |
C6—C7—C8—O18 | 177.5 (4) | C14A—C15A—C16A—C11A | 1.8 (16) |
C6—C7—C8—C9 | −1.3 (7) | C9—C10—O1B—C2B | 169.1 (7) |
O18—C8—C9—C10 | −178.0 (4) | C5—C10—O1B—C2B | −1.6 (10) |
C7—C8—C9—C10 | 0.7 (6) | C10—O1B—C2B—C3B | 17.8 (14) |
C8—C9—C10—O1A | 173.5 (5) | C10—O1B—C2B—C11B | 163.4 (7) |
C8—C9—C10—O1B | −169.5 (5) | O1B—C2B—C3B—C4 | −17.8 (16) |
C8—C9—C10—C5 | 1.3 (6) | C11B—C2B—C3B—C4 | −159.3 (9) |
C6—C5—C10—O1A | −174.3 (5) | O17—C4—C3B—C2B | −167.1 (8) |
C4—C5—C10—O1A | 4.9 (7) | C5—C4—C3B—C2B | 2.6 (13) |
C6—C5—C10—O1B | 167.7 (6) | C3B—C2B—C11B—C16B | −107.0 (13) |
C4—C5—C10—O1B | −13.1 (7) | O1B—C2B—C11B—C16B | 106.3 (11) |
C6—C5—C10—C9 | −2.7 (6) | C3B—C2B—C11B—C12B | 74.0 (17) |
C4—C5—C10—C9 | 176.5 (4) | O1B—C2B—C11B—C12B | −72.7 (15) |
C9—C10—O1A—C2A | −163.7 (5) | C16B—C11B—C12B—C13B | 1.1 (19) |
C5—C10—O1A—C2A | 8.3 (9) | C2B—C11B—C12B—C13B | −180.0 (10) |
C10—O1A—C2A—C3A | −20.7 (11) | C11B—C12B—C13B—C14B | −1.4 (19) |
C10—O1A—C2A—C11A | −163.5 (6) | C12B—C13B—C14B—C15B | 0.4 (18) |
O1A—C2A—C3A—C4 | 19.2 (13) | C13B—C14B—C15B—C16B | 1 (2) |
C11A—C2A—C3A—C4 | 158.2 (7) | C14B—C15B—C16B—C11B | −1 (3) |
O17—C4—C3A—C2A | 166.8 (7) | C12B—C11B—C16B—C15B | 0 (2) |
C5—C4—C3A—C2A | −5.7 (11) | C2B—C11B—C16B—C15B | −178.9 (15) |
Cg3, Cg4 and Cg5 are the centroid of the C5–C10, C11A–C16A and C11B–C16B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13A—H13A···Cg4i | 0.93 | 2.80 | 3.598 (11) | 144 |
C13A—H13A···Cg5i | 0.93 | 2.71 | 3.515 (11) | 146 |
C13B—H13B···Cg4i | 0.93 | 2.82 | 3.695 (12) | 158 |
C13B—H13B···Cg5i | 0.93 | 2.76 | 3.639 (13) | 157 |
C19—H19B···Cg4ii | 0.96 | 2.72 | 3.619 (7) | 156 |
C19—H19B···Cg5ii | 0.96 | 2.76 | 3.660 (7) | 157 |
C15B—H15B···Cg3iii | 0.93 | 2.65 | 3.497 (14) | 151 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H14O3 |
Mr | 254.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 8.5600 (3), 6.6320 (2), 23.4130 (7) |
β (°) | 90.742 (2) |
V (Å3) | 1329.04 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.55 × 0.16 × 0.10 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.954, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15170, 2710, 1765 |
Rint | 0.072 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.086, 0.280, 1.18 |
No. of reflections | 2710 |
No. of parameters | 165 |
No. of restraints | 122 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.65, −0.35 |
Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), publCIF (Westrip, 2010).
Cg3, Cg4 and Cg5 are the centroid of the C5–C10, C11A–C16A and C11B–C16B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13A—H13A···Cg4i | 0.93 | 2.80 | 3.598 (11) | 144 |
C13A—H13A···Cg5i | 0.93 | 2.71 | 3.515 (11) | 146 |
C13B—H13B···Cg4i | 0.93 | 2.82 | 3.695 (12) | 158 |
C13B—H13B···Cg5i | 0.93 | 2.76 | 3.639 (13) | 157 |
C19—H19B···Cg4ii | 0.96 | 2.72 | 3.619 (7) | 156 |
C19—H19B···Cg5ii | 0.96 | 2.76 | 3.660 (7) | 157 |
C15B—H15B···Cg3iii | 0.93 | 2.65 | 3.497 (14) | 151 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x−1, y, z. |
Acknowledgements
The authors thank the Joint X-ray Laboratory, Faculty of Chemistry, Jagiellonian University, for making the Nonius KappaCCD diffractometer available.
References
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Flavanones are of interest because of their anticancer effect as the aromatase inhibitors. By competing with androgens for binding with aromatase these compounds prevent the hydroxylation of C18 androgens to aromatic C19 estrogenic steroids (Hong & Chen, 2006). This suppresses the overexpression of aromatase in breast cancer (Pouget et al., 2001).
The heterocyclic ring contains O1, C2 and C3 atoms exhibiting static disorder. This disorder is propagated into the attached phenyl. The dihedral angle between the C5—C10 aromatic ring plane and the phenyl ring plane is 88.6 (1)° for the major disorder component (C11A—C16A) and 87.3 (1)° for the minor component (C11B—C16B). The structure is stabilized by π–π and C—H···π interactions (Table 1). The C5—C10 ring displays a π–π interaction with the C5i—C10i ring (Fig. 2 b) with a perpendicular distance of 3.543 (1) Å, a centroid-to-centroid distance of 3.912 (1) Å and a slippage of 1.658 Å [symmetry code: (i) 1 - x, -y, -z]. There are three types of C—H···π interactions: C13A—H13A···Cg4i (C13B—13B··· Cg4i in the minor disorder component), C19—H19B··· Cg4ii (Fig. 2a) and C15B—H15B···Cg3iii (Fig. 2 a) [symmetry codes: (i) -x, y+1/2, 1/2-z, (ii) 1 - x, 1 - y, -z, (iii) x - 1, y, z]. The first interaction falls into type III X—H···pi interactions while the rest can be classified as type I according to Malone and coworkers (Malone et al. (1997)).