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In the title compound, C20H18O3, the phenyl ring makes a dihedral angle of 50.41 (10)° with the benzene ring of the chromanone unit. The mol­ecular structure is stabilized by weak intra­molecular C—H...O inter­actions and the crystal packing is stabilized by weak inter­molecular C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051161/bt2548sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051161/bt2548Isup2.hkl
Contains datablock I

CCDC reference: 667408

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.068
  • wR factor = 0.183
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.94
Author Response: The data were collected on an a STOE IPDS II diffractometer with an image plate detector. The crystal was very thin (SIZE 0.18 0.11 0.06) and although the exposure time was set rather high (5 min.) the weak reflections ratio was high, so the unique data ratio above the 2 sigma level is low. Temperature [K] : 150 Exposure time [min] : 5.0

Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 27.17 From the CIF: _diffrn_reflns_theta_full 27.17 From the CIF: _reflns_number_total 3177 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3387 Completeness (_total/calc) 93.80% RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.133 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13 PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 7 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The chromanone moiety present in the title compound consisting of the pyrone ring and benzene ring plays an important role in many areas of medicines such as inhibition of HIV replication (Tillekeratne et al., 2001). The naturally occurring classes of compounds to which they belong, the benzylidene chroman-4-ones have been identified as a potential source of new anti-fungal agents (Jae Gon Kang et al., 2004).

The geometric parameters in the title compound agree with the reported values of similar structures (Puviarasan et al., 1998; Wu et al., 2005a,b; Schollmeyer et al., 2005; Nissa et al., 2001). The chromanone moiety consists of one benzene ring fused with a six membered heterocyclic ring, which adopts a half-chair conformation. The phenyl ring makes a dihedral angle of 50.41 (10) ° with the benzene ring of chromanone unit.

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak intermolecular C—H···O interactions.

Related literature top

For related lituerature see: Puviarasan et al., (1998); Tillekeratne et al.,(2001); Nissa et al., (2001);Jae Gon Kang et al., (2004); Wu et al., (2005a,b); Schollmeyer et al., (2005).

Experimental top

10 mmol of Methyl-2-bromomethyl-3-phenyl-propenoate was treated with 10 mmol of eugenol in the presence of potassium carbonate in acetone at reflux temperature for 3 hrs. The pure ester of methyl- 3-phenyl-2-(2-methoxy-4- prop-2-enyl)phenoxy methyl-prop- 2enoate was obtained after silica gel column chromatography (3% EtOAc- hexane). Hydrolysis of this ester was carried out with KOH in aquous 1,4 –Dioxane at room temperature. The reaction mixture was acidified and the precipitated acid was purified by recrystalization. Finally the acid was treated with TFAA and the reaction mixture refluxed in dichloro- methane for 1 hr. It was further purified by column chromatography (silica gel-3% EtOAc- hexane).

Refinement top

H atoms were positioned geometrically and refined using riding model with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.99 Å and Uiso(H) = 1.2Ueq(C) for CH2, C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C) for CH3.

Structure description top

The chromanone moiety present in the title compound consisting of the pyrone ring and benzene ring plays an important role in many areas of medicines such as inhibition of HIV replication (Tillekeratne et al., 2001). The naturally occurring classes of compounds to which they belong, the benzylidene chroman-4-ones have been identified as a potential source of new anti-fungal agents (Jae Gon Kang et al., 2004).

The geometric parameters in the title compound agree with the reported values of similar structures (Puviarasan et al., 1998; Wu et al., 2005a,b; Schollmeyer et al., 2005; Nissa et al., 2001). The chromanone moiety consists of one benzene ring fused with a six membered heterocyclic ring, which adopts a half-chair conformation. The phenyl ring makes a dihedral angle of 50.41 (10) ° with the benzene ring of chromanone unit.

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak intermolecular C—H···O interactions.

For related lituerature see: Puviarasan et al., (1998); Tillekeratne et al.,(2001); Nissa et al., (2001);Jae Gon Kang et al., (2004); Wu et al., (2005a,b); Schollmeyer et al., (2005).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids for non-H atoms.
3-Benzylidene-8-methoxy-6-(prop-1-enyl)chroman-4-one top
Crystal data top
C20H18O3F(000) = 648
Mr = 306.34Dx = 1.334 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.0763 (8) ÅCell parameters from 9395 reflections
b = 6.9018 (7) Åθ = 1.9–27.2°
c = 22.1841 (18) ŵ = 0.09 mm1
β = 98.690 (7)°T = 150 K
V = 1525.1 (2) Å3Prism, yellow
Z = 40.18 × 0.11 × 0.06 mm
Data collection top
Stoe IPDS2
diffractometer
3177 independent reflections
Radiation source: fine-focus sealed tube1494 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.133
Detector resolution: 6.67 pixels mm-1θmax = 27.2°, θmin = 1.9°
rotation method scansh = 1212
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 88
Tmin = 0.984, Tmax = 0.995l = 2828
11793 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.0793P)2]
where P = (Fo2 + 2Fc2)/3
3177 reflections(Δ/σ)max = 0.002
210 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C20H18O3V = 1525.1 (2) Å3
Mr = 306.34Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.0763 (8) ŵ = 0.09 mm1
b = 6.9018 (7) ÅT = 150 K
c = 22.1841 (18) Å0.18 × 0.11 × 0.06 mm
β = 98.690 (7)°
Data collection top
Stoe IPDS2
diffractometer
3177 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
1494 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.995Rint = 0.133
11793 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.183H-atom parameters constrained
S = 0.92Δρmax = 0.21 e Å3
3177 reflectionsΔρmin = 0.28 e Å3
210 parameters
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
O10.1367 (2)0.6980 (3)0.13018 (11)0.0438 (6)
O20.0608 (2)0.6743 (4)0.27802 (11)0.0512 (7)
C100.0003 (3)0.7017 (5)0.12271 (16)0.0412 (8)
C110.0732 (3)0.6822 (4)0.17019 (15)0.0394 (8)
O30.0178 (2)0.7463 (4)0.01969 (11)0.0485 (6)
C80.1466 (3)0.6369 (5)0.23959 (16)0.0409 (8)
C150.2804 (3)0.7204 (5)0.09918 (16)0.0406 (8)
C10.3676 (3)0.6343 (5)0.31085 (16)0.0405 (8)
C160.2138 (3)0.6905 (5)0.15790 (17)0.0430 (8)
H160.26440.67540.19040.052*
C180.4281 (3)0.7281 (5)0.08759 (17)0.0450 (8)
H180.47280.71730.12220.054*
C60.4472 (3)0.5143 (5)0.28020 (16)0.0437 (8)
H60.40560.43320.24820.052*
C120.0010 (3)0.6639 (5)0.23362 (16)0.0415 (8)
C50.5854 (4)0.5116 (5)0.29567 (16)0.0442 (8)
H50.63760.42980.27400.053*
C140.2031 (3)0.7411 (5)0.05181 (16)0.0429 (8)
H140.24710.76200.01140.052*
C130.0650 (3)0.7318 (5)0.06266 (16)0.0426 (8)
C70.2216 (3)0.6554 (4)0.29504 (17)0.0420 (8)
H70.17430.68580.32780.050*
C90.1985 (3)0.5868 (5)0.18191 (16)0.0422 (8)
H9A0.29660.60880.18770.051*
H9B0.18250.44730.17320.051*
C190.5049 (4)0.7483 (5)0.03451 (17)0.0494 (9)
H190.46070.75960.00020.059*
C40.6485 (4)0.6273 (5)0.34257 (16)0.0452 (8)
H40.74340.62540.35300.054*
C20.4336 (4)0.7471 (5)0.35922 (16)0.0443 (8)
H20.38230.82580.38220.053*
C30.5720 (4)0.7448 (5)0.37377 (16)0.0471 (8)
H30.61470.82530.40570.057*
C200.6550 (3)0.7552 (6)0.02331 (18)0.0536 (10)
H20A0.68910.75380.06240.080*
H20B0.68970.64220.00090.080*
H20C0.68460.87390.00100.080*
C170.0458 (4)0.7642 (6)0.04259 (16)0.0532 (9)
H17A0.10300.65110.05370.080*
H17B0.02310.77180.06940.080*
H17C0.10070.88200.04720.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0293 (12)0.0611 (15)0.0418 (14)0.0009 (10)0.0082 (11)0.0041 (10)
O20.0401 (15)0.0729 (17)0.0420 (15)0.0049 (11)0.0110 (13)0.0008 (12)
C100.0328 (18)0.0476 (18)0.044 (2)0.0005 (13)0.0081 (17)0.0013 (14)
C110.0348 (19)0.0438 (18)0.040 (2)0.0007 (13)0.0063 (16)0.0003 (14)
O30.0370 (14)0.0714 (16)0.0381 (13)0.0002 (11)0.0089 (12)0.0027 (11)
C80.0345 (19)0.0481 (19)0.040 (2)0.0010 (13)0.0075 (18)0.0003 (15)
C150.0338 (18)0.0448 (18)0.044 (2)0.0004 (13)0.0101 (17)0.0032 (14)
C10.0374 (19)0.0442 (18)0.040 (2)0.0014 (13)0.0058 (17)0.0038 (14)
C160.0355 (19)0.0499 (19)0.045 (2)0.0003 (14)0.0096 (17)0.0009 (15)
C180.0358 (19)0.053 (2)0.048 (2)0.0018 (15)0.0113 (18)0.0032 (16)
C60.040 (2)0.0484 (19)0.042 (2)0.0030 (14)0.0048 (18)0.0024 (15)
C120.039 (2)0.0463 (18)0.040 (2)0.0016 (13)0.0070 (17)0.0002 (14)
C50.043 (2)0.0467 (19)0.044 (2)0.0053 (14)0.0091 (18)0.0028 (15)
C140.0374 (19)0.0474 (18)0.043 (2)0.0006 (14)0.0037 (16)0.0028 (15)
C130.037 (2)0.0496 (19)0.042 (2)0.0019 (14)0.0106 (17)0.0006 (15)
C70.038 (2)0.0455 (19)0.044 (2)0.0007 (13)0.0110 (18)0.0000 (15)
C90.0341 (19)0.0524 (19)0.039 (2)0.0045 (14)0.0031 (17)0.0002 (15)
C190.041 (2)0.063 (2)0.045 (2)0.0059 (16)0.0093 (19)0.0038 (17)
C40.038 (2)0.052 (2)0.045 (2)0.0002 (14)0.0044 (18)0.0045 (16)
C20.041 (2)0.053 (2)0.0392 (19)0.0012 (15)0.0072 (17)0.0018 (15)
C30.045 (2)0.053 (2)0.043 (2)0.0042 (15)0.0046 (18)0.0019 (16)
C200.034 (2)0.070 (2)0.057 (2)0.0005 (16)0.0072 (19)0.0014 (19)
C170.046 (2)0.077 (3)0.037 (2)0.0006 (18)0.0081 (18)0.0043 (18)
Geometric parameters (Å, º) top
O1—C101.360 (4)C6—H60.9500
O1—C91.441 (4)C5—C41.387 (5)
O2—C121.232 (4)C5—H50.9500
C10—C111.383 (4)C14—C131.377 (5)
C10—C131.409 (5)C14—H140.9500
C11—C161.403 (5)C7—H70.9500
C11—C121.489 (5)C9—H9A0.9900
O3—C131.362 (4)C9—H9B0.9900
O3—C171.438 (4)C19—C201.496 (5)
C8—C71.349 (5)C19—H190.9500
C8—C121.485 (5)C4—C31.375 (5)
C8—C91.494 (4)C4—H40.9500
C15—C161.387 (5)C2—C31.383 (5)
C15—C141.407 (4)C2—H20.9500
C15—C181.473 (5)C3—H30.9500
C1—C61.399 (4)C20—H20A0.9800
C1—C21.408 (5)C20—H20B0.9800
C1—C71.467 (5)C20—H20C0.9800
C16—H160.9500C17—H17A0.9800
C18—C191.315 (5)C17—H17B0.9800
C18—H180.9500C17—H17C0.9800
C6—C51.383 (5)
C10—O1—C9114.4 (2)O3—C13—C10115.1 (3)
O1—C10—C11123.6 (3)C14—C13—C10119.2 (3)
O1—C10—C13115.9 (3)C8—C7—C1127.8 (3)
C11—C10—C13120.5 (3)C8—C7—H7116.1
C10—C11—C16119.3 (3)C1—C7—H7116.1
C10—C11—C12119.1 (3)O1—C9—C8113.2 (3)
C16—C11—C12121.5 (3)O1—C9—H9A108.9
C13—O3—C17116.6 (3)C8—C9—H9A108.9
C7—C8—C12119.0 (3)O1—C9—H9B108.9
C7—C8—C9125.6 (3)C8—C9—H9B108.9
C12—C8—C9115.3 (3)H9A—C9—H9B107.8
C16—C15—C14118.2 (3)C18—C19—C20126.6 (3)
C16—C15—C18120.1 (3)C18—C19—H19116.7
C14—C15—C18121.7 (3)C20—C19—H19116.7
C6—C1—C2117.3 (3)C3—C4—C5119.3 (3)
C6—C1—C7124.8 (3)C3—C4—H4120.4
C2—C1—C7117.9 (3)C5—C4—H4120.4
C15—C16—C11121.3 (3)C3—C2—C1121.0 (3)
C15—C16—H16119.4C3—C2—H2119.5
C11—C16—H16119.4C1—C2—H2119.5
C19—C18—C15127.1 (3)C4—C3—C2120.7 (3)
C19—C18—H18116.5C4—C3—H3119.6
C15—C18—H18116.5C2—C3—H3119.6
C5—C6—C1121.1 (3)C19—C20—H20A109.5
C5—C6—H6119.4C19—C20—H20B109.5
C1—C6—H6119.4H20A—C20—H20B109.5
O2—C12—C8122.7 (3)C19—C20—H20C109.5
O2—C12—C11121.5 (3)H20A—C20—H20C109.5
C8—C12—C11115.8 (3)H20B—C20—H20C109.5
C6—C5—C4120.5 (3)O3—C17—H17A109.5
C6—C5—H5119.7O3—C17—H17B109.5
C4—C5—H5119.7H17A—C17—H17B109.5
C13—C14—C15121.6 (3)O3—C17—H17C109.5
C13—C14—H14119.2H17A—C17—H17C109.5
C15—C14—H14119.2H17B—C17—H17C109.5
O3—C13—C14125.7 (3)
C9—O1—C10—C1127.8 (4)C16—C15—C14—C130.2 (5)
C9—O1—C10—C13153.7 (3)C18—C15—C14—C13179.3 (3)
O1—C10—C11—C16179.2 (3)C17—O3—C13—C142.9 (5)
C13—C10—C11—C160.7 (5)C17—O3—C13—C10176.0 (3)
O1—C10—C11—C122.6 (5)C15—C14—C13—O3178.6 (3)
C13—C10—C11—C12175.9 (3)C15—C14—C13—C100.3 (5)
C14—C15—C16—C110.4 (5)O1—C10—C13—O32.3 (4)
C18—C15—C16—C11179.9 (3)C11—C10—C13—O3179.2 (3)
C10—C11—C16—C150.8 (5)O1—C10—C13—C14178.7 (3)
C12—C11—C16—C15175.7 (3)C11—C10—C13—C140.2 (5)
C16—C15—C18—C19177.4 (3)C12—C8—C7—C1179.8 (3)
C14—C15—C18—C192.1 (5)C9—C8—C7—C11.1 (5)
C2—C1—C6—C52.0 (5)C6—C1—C7—C829.5 (5)
C7—C1—C6—C5176.0 (3)C2—C1—C7—C8148.4 (3)
C7—C8—C12—O211.0 (5)C10—O1—C9—C849.7 (4)
C9—C8—C12—O2167.9 (3)C7—C8—C9—O1138.7 (3)
C7—C8—C12—C11167.7 (3)C12—C8—C9—O142.5 (4)
C9—C8—C12—C1113.4 (4)C15—C18—C19—C20179.8 (4)
C10—C11—C12—O2169.4 (3)C6—C5—C4—C30.2 (5)
C16—C11—C12—O27.1 (5)C6—C1—C2—C32.8 (5)
C10—C11—C12—C89.4 (4)C7—C1—C2—C3175.4 (3)
C16—C11—C12—C8174.1 (3)C5—C4—C3—C20.6 (5)
C1—C6—C5—C40.6 (5)C1—C2—C3—C42.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O20.952.462.817 (4)102
C9—H9B···O2i0.992.573.345 (4)135
C20—H20A···O1ii0.982.513.418 (4)154
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC20H18O3
Mr306.34
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)10.0763 (8), 6.9018 (7), 22.1841 (18)
β (°) 98.690 (7)
V3)1525.1 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.18 × 0.11 × 0.06
Data collection
DiffractometerStoe IPDS2
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.984, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
11793, 3177, 1494
Rint0.133
(sin θ/λ)max1)0.642
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.183, 0.92
No. of reflections3177
No. of parameters210
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.28

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O20.952.462.817 (4)102.2
C9—H9B···O2i0.992.573.345 (4)134.8
C20—H20A···O1ii0.982.513.418 (4)154.3
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x1, y, z.
 

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