Literature DB >> 23424545

7-Meth-oxy-2-phenyl-chroman-4-one.

Agata Piaskowska1, Maciej Hodorowicz, Wojciech Nitek.   

Abstract

In the title compound, C(16)H(14)O(3), 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 inter-actions.

Entities:  

Year:  2013        PMID： 23424545      PMCID： PMC3569799          DOI： 10.1107/S1600536813001451

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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

C16H14O3 M = 254.27 Monoclinic, a = 8.5600 (3) Å b = 6.6320 (2) Å c = 23.4130 (7) Å β = 90.742 (2)° V = 1329.04 (7) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 293 K 0.55 × 0.16 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997 ▶) T min = 0.954, T max = 0.991 15170 measured reflections 2710 independent reflections 1765 reflections with I > 2σ(I) R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.086 wR(F 2) = 0.280 S = 1.18 2710 reflections 165 parameters 122 restraints H-atom parameters constrained Δρmax = 0.65 e Å−3 Δρmin = −0.35 e Å−3 Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: 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 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001451/kj2213sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001451/kj2213Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813001451/kj2213Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H14O3F(000) = 536
Mr = 254.27Dx = 1.271 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 13054 reflections
a = 8.5600 (3) Åθ = 0.4–26.4°
b = 6.6320 (2) ŵ = 0.09 mm−1
c = 23.4130 (7) ÅT = 293 K
β = 90.742 (2)°Prism, colourless
V = 1329.04 (7) Å30.55 × 0.16 × 0.10 mm
Z = 4
Nonius KappaCCD diffractometer2710 independent reflections
Radiation source: fine-focus sealed tube1765 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.072
Detector resolution: 9 pixels mm-1θmax = 26.4°, θmin = 2.9°
CCD scansh = −8→10
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)k = −8→8
Tmin = 0.954, Tmax = 0.991l = −29→29
15170 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.280H-atom parameters constrained
S = 1.18w = 1/[σ2(Fo2) + (0.1433P)2 + 0.4478P] where P = (Fo2 + 2Fc2)/3
2710 reflections(Δ/σ)max < 0.001
165 parametersΔρmax = 0.65 e Å−3
122 restraintsΔρmin = −0.35 e Å−3
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.
xyzUiso*/UeqOcc. (<1)
O170.5477 (4)−0.2944 (5)0.18360 (14)0.0728 (11)
O180.8157 (4)0.1840 (5)−0.02843 (13)0.0638 (9)
C40.5036 (5)−0.1399 (6)0.15982 (17)0.0534 (11)
C50.5802 (5)−0.0580 (6)0.10887 (16)0.0476 (10)
C60.7077 (5)−0.1537 (7)0.08388 (19)0.0592 (12)
H60.7426−0.27590.09880.071*
C70.7821 (5)−0.0726 (7)0.03831 (18)0.0577 (12)
H70.8668−0.13860.02240.069*
C80.7298 (5)0.1117 (6)0.01556 (16)0.0483 (10)
C90.6034 (5)0.2073 (6)0.03813 (16)0.0483 (10)
H90.56840.32860.02270.058*
C100.5271 (4)0.1219 (6)0.08444 (15)0.0429 (9)
C190.7766 (7)0.3789 (8)−0.0506 (2)0.0777 (16)
H19A0.66950.3793−0.06340.116*
H19B0.84310.4098−0.08220.116*
H19C0.79080.4784−0.02130.116*
O1A0.4127 (8)0.2362 (10)0.1081 (3)0.043 (2)*0.559 (12)
C2A0.3587 (8)0.1876 (10)0.1623 (3)0.043 (2)*0.559 (12)
H2A0.42890.26770.18670.052*0.559 (12)
C3A0.3801 (12)−0.0050 (14)0.1850 (4)0.049 (3)*0.559 (12)
H3A10.2810−0.07540.18190.059*0.559 (12)
H3A20.40390.01000.22540.059*0.559 (12)
C11A0.2053 (10)0.2932 (13)0.1710 (4)0.047 (2)*0.559 (12)
C12A0.2038 (13)0.4478 (18)0.2065 (6)0.065 (4)*0.559 (12)
H12A0.29610.48050.22580.078*0.559 (12)
C13A0.0813 (12)0.5567 (15)0.2160 (4)0.062 (3)*0.559 (12)
H13A0.09010.66570.24080.074*0.559 (12)
C14A−0.0591 (11)0.5178 (13)0.1912 (4)0.050 (2)*0.559 (12)
H14A−0.14530.59770.19920.060*0.559 (12)
C15A−0.0727 (12)0.3545 (19)0.1530 (5)0.068 (4)*0.559 (12)
H15A−0.16780.32220.13560.082*0.559 (12)
C16A0.0671 (13)0.2391 (16)0.1419 (5)0.061 (3)*0.559 (12)
H16A0.06550.13220.11620.073*0.559 (12)
O1B0.3856 (10)0.2064 (12)0.0994 (3)0.036 (2)*0.441 (12)
C2B0.2931 (11)0.1055 (15)0.1386 (4)0.050 (3)*0.441 (12)
H2B0.22760.02440.11280.060*0.441 (12)
C3B0.3513 (14)−0.0439 (19)0.1748 (5)0.046 (3)*0.441 (12)
H3B10.2734−0.14970.17700.055*0.441 (12)
H3B20.36240.01370.21270.055*0.441 (12)
C11B0.1728 (13)0.2564 (14)0.1603 (4)0.040 (3)*0.441 (12)
C12B0.1843 (14)0.424 (2)0.1974 (7)0.062 (5)*0.441 (12)
H12B0.27920.46170.21400.074*0.441 (12)
C13B0.0404 (14)0.5362 (17)0.2086 (5)0.052 (3)*0.441 (12)
H13B0.03930.64630.23330.062*0.441 (12)
C14B−0.0916 (11)0.4712 (16)0.1813 (4)0.044 (3)*0.441 (12)
H14B−0.18520.53880.18710.053*0.441 (12)
C15B−0.0895 (15)0.313 (2)0.1463 (7)0.068 (5)*0.441 (12)
H15B−0.18180.27470.12800.082*0.441 (12)
C16B0.0329 (14)0.213 (2)0.1373 (6)0.063 (5)*0.441 (12)
H16B0.02560.10260.11300.076*0.441 (12)
U11U22U33U12U13U23
O170.072 (2)0.069 (2)0.078 (2)0.0210 (17)0.0127 (17)0.0313 (17)
O180.065 (2)0.063 (2)0.0643 (18)0.0106 (15)0.0277 (15)0.0115 (14)
C40.054 (3)0.053 (2)0.053 (2)0.004 (2)0.0016 (19)0.0095 (19)
C50.045 (2)0.048 (2)0.050 (2)0.0077 (18)0.0035 (17)0.0043 (17)
C60.058 (3)0.053 (2)0.066 (3)0.015 (2)0.007 (2)0.011 (2)
C70.052 (3)0.059 (3)0.063 (3)0.015 (2)0.017 (2)0.003 (2)
C80.045 (2)0.053 (2)0.047 (2)0.0039 (18)0.0085 (17)0.0032 (17)
C90.050 (2)0.046 (2)0.049 (2)0.0081 (18)0.0058 (18)0.0056 (16)
C100.041 (2)0.046 (2)0.0426 (19)0.0041 (16)0.0048 (16)−0.0013 (16)
C190.095 (4)0.065 (3)0.074 (3)0.008 (3)0.036 (3)0.016 (2)
O17—C41.224 (5)C11A—C16A1.404 (12)
O18—C81.361 (5)C12A—C13A1.295 (11)
O18—C191.432 (6)C12A—H12A0.9300
C4—C51.472 (6)C13A—C14A1.353 (11)
C4—C3B1.496 (12)C13A—H13A0.9300
C4—C3A1.510 (10)C14A—C15A1.409 (12)
C5—C101.397 (5)C14A—H14A0.9300
C5—C61.398 (6)C15A—C16A1.447 (12)
C6—C71.360 (6)C15A—H15A0.9300
C6—H60.9300C16A—H16A0.9300
C7—C81.404 (6)O1B—C2B1.392 (11)
C7—H70.9300C2B—C3B1.391 (14)
C8—C91.366 (5)C2B—C11B1.527 (13)
C9—C101.393 (5)C2B—H2B0.9800
C9—H90.9300C3B—H3B10.9700
C10—O1A1.362 (7)C3B—H3B20.9700
C10—O1B1.384 (8)C11B—C16B1.337 (13)
C19—H19A0.9600C11B—C12B1.414 (13)
C19—H19B0.9600C12B—C13B1.465 (13)
C19—H19C0.9600C12B—H12B0.9300
O1A—C2A1.394 (9)C13B—C14B1.362 (13)
C2A—C3A1.395 (11)C13B—H13B0.9300
C2A—C11A1.504 (10)C14B—C15B1.330 (13)
C2A—H2A0.9800C14B—H14B0.9300
C3A—H3A10.9700C15B—C16B1.260 (13)
C3A—H3A20.9700C15B—H15B0.9300
C11A—C12A1.321 (12)C16B—H16B0.9300
C8—O18—C19117.8 (3)C12A—C11A—C2A117.5 (8)
O17—C4—C5122.6 (4)C16A—C11A—C2A123.2 (8)
O17—C4—C3B121.0 (5)C13A—C12A—C11A123.8 (10)
C5—C4—C3B115.5 (5)C13A—C12A—H12A118.1
O17—C4—C3A122.1 (5)C11A—C12A—H12A118.1
C5—C4—C3A114.8 (5)C12A—C13A—C14A122.4 (9)
C3B—C4—C3A16.3 (6)C12A—C13A—H13A118.8
C10—C5—C6117.9 (4)C14A—C13A—H13A118.8
C10—C5—C4120.1 (3)C13A—C14A—C15A119.0 (7)
C6—C5—C4122.0 (4)C13A—C14A—H14A120.5
C7—C6—C5121.6 (4)C15A—C14A—H14A120.5
C7—C6—H6119.2C14A—C15A—C16A117.3 (8)
C5—C6—H6119.2C14A—C15A—H15A121.4
C6—C7—C8119.4 (4)C16A—C15A—H15A121.4
C6—C7—H7120.3C11A—C16A—C15A118.1 (8)
C8—C7—H7120.3C11A—C16A—H16A120.9
O18—C8—C9124.6 (4)C15A—C16A—H16A120.9
O18—C8—C7114.9 (3)C10—O1B—C2B118.7 (6)
C9—C8—C7120.5 (4)C3B—C2B—O1B122.8 (9)
C8—C9—C10119.6 (4)C3B—C2B—C11B120.2 (8)
C8—C9—H9120.2O1B—C2B—C11B107.2 (7)
C10—C9—H9120.2C3B—C2B—H2B100.5
O1A—C10—O1B15.2 (4)O1B—C2B—H2B100.5
O1A—C10—C9115.9 (4)C11B—C2B—H2B100.5
O1B—C10—C9116.9 (4)C2B—C3B—C4117.9 (8)
O1A—C10—C5122.8 (4)C2B—C3B—H3B1107.8
O1B—C10—C5121.6 (4)C4—C3B—H3B1107.8
C9—C10—C5120.9 (3)C2B—C3B—H3B2107.8
O18—C19—H19A109.5C4—C3B—H3B2107.8
O18—C19—H19B109.5H3B1—C3B—H3B2107.2
H19A—C19—H19B109.5C16B—C11B—C12B118.0 (8)
O18—C19—H19C109.5C16B—C11B—C2B109.3 (9)
H19A—C19—H19C109.5C12B—C11B—C2B132.7 (10)
H19B—C19—H19C109.5C11B—C12B—C13B117.3 (9)
C10—O1A—C2A119.3 (5)C11B—C12B—H12B121.4
O1A—C2A—C3A121.0 (6)C13B—C12B—H12B121.4
O1A—C2A—C11A108.4 (6)C14B—C13B—C12B116.6 (9)
C3A—C2A—C11A119.0 (7)C14B—C13B—H13B121.7
O1A—C2A—H2A101.4C12B—C13B—H13B121.7
C3A—C2A—H2A101.4C15B—C14B—C13B121.5 (9)
C11A—C2A—H2A101.4C15B—C14B—H14B119.3
C2A—C3A—C4118.9 (7)C13B—C14B—H14B119.3
C2A—C3A—H3A1107.6C16B—C15B—C14B122.3 (11)
C4—C3A—H3A1107.6C16B—C15B—H15B118.8
C2A—C3A—H3A2107.6C14B—C15B—H15B118.8
C4—C3A—H3A2107.6C15B—C16B—C11B124.3 (11)
H3A1—C3A—H3A2107.0C15B—C16B—H16B117.9
C12A—C11A—C16A119.3 (8)C11B—C16B—H16B117.9
O17—C4—C5—C10−178.3 (4)O1A—C2A—C11A—C12A−107.5 (10)
C3B—C4—C5—C1012.2 (8)C3A—C2A—C11A—C12A108.8 (11)
C3A—C4—C5—C10−5.9 (7)O1A—C2A—C11A—C16A70.2 (10)
O17—C4—C5—C60.8 (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—C6173.3 (6)C2A—C11A—C12A—C13A177.1 (11)
C10—C5—C6—C72.1 (7)C11A—C12A—C13A—C14A2 (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—C93.7 (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—O18177.5 (4)C14A—C15A—C16A—C11A1.8 (16)
C6—C7—C8—C9−1.3 (7)C9—C10—O1B—C2B169.1 (7)
O18—C8—C9—C10−178.0 (4)C5—C10—O1B—C2B−1.6 (10)
C7—C8—C9—C100.7 (6)C10—O1B—C2B—C3B17.8 (14)
C8—C9—C10—O1A173.5 (5)C10—O1B—C2B—C11B163.4 (7)
C8—C9—C10—O1B−169.5 (5)O1B—C2B—C3B—C4−17.8 (16)
C8—C9—C10—C51.3 (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—O1A4.9 (7)C5—C4—C3B—C2B2.6 (13)
C6—C5—C10—O1B167.7 (6)C3B—C2B—C11B—C16B−107.0 (13)
C4—C5—C10—O1B−13.1 (7)O1B—C2B—C11B—C16B106.3 (11)
C6—C5—C10—C9−2.7 (6)C3B—C2B—C11B—C12B74.0 (17)
C4—C5—C10—C9176.5 (4)O1B—C2B—C11B—C12B−72.7 (15)
C9—C10—O1A—C2A−163.7 (5)C16B—C11B—C12B—C13B1.1 (19)
C5—C10—O1A—C2A8.3 (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—C15B0.4 (18)
O1A—C2A—C3A—C419.2 (13)C13B—C14B—C15B—C16B1 (2)
C11A—C2A—C3A—C4158.2 (7)C14B—C15B—C16B—C11B−1 (3)
O17—C4—C3A—C2A166.8 (7)C12B—C11B—C16B—C15B0 (2)
C5—C4—C3A—C2A−5.7 (11)C2B—C11B—C16B—C15B−178.9 (15)
D—H···AD—HH···AD···AD—H···A
C13A—H13A···Cg4i0.932.803.598 (11)144
C13A—H13A···Cg5i0.932.713.515 (11)146
C13B—H13B···Cg4i0.932.823.695 (12)158
C13B—H13B···Cg5i0.932.763.639 (13)157
C19—H19B···Cg4ii0.962.723.619 (7)156
C19—H19B···Cg5ii0.962.763.660 (7)157
C15B—H15B···Cg3iii0.932.653.497 (14)151
Table 1

Hydrogen-bond geometry (Å, °)

Cg3, Cg4 and Cg5 are the centroids of the C5–C10, C11A–C16A and C11B–C16B rings, respectively.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C13A—H13A⋯Cg4i 0.932.803.598 (11)144
C13A—H13A⋯Cg5i 0.932.713.515 (11)146
C13B—H13B⋯Cg4i 0.932.823.695 (12)158
C13B—H13B⋯Cg5i 0.932.763.639 (13)157
C19—H19B⋯Cg4ii 0.962.723.619 (7)156
C19—H19B⋯Cg5ii 0.962.763.660 (7)157
C15B—H15B⋯Cg3iii 0.932.653.497 (14)151

Symmetry codes: (i) ; (ii) ; (iii) .

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