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In the title compound, C18H16O3, the phenyl ring makes a dihedral angle of 59.67 (4)° with the benzene ring of the chromanone unit. The mol­ecular structure is stabilized by a weak intra­molecular C—H...O inter­action and the crystal packing is stabilized by weak inter­molecular C—H...O and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053019/is2223sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053019/is2223Isup2.hkl
Contains datablock I

CCDC reference: 672807

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.039
  • wR factor = 0.099
  • Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 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 and benzene rings 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 benzylidine chroman-4-ones, have been identified as a potential source of new anti-fungal agents (Kang et al., 2004).

The geometric parameters in the compound, (I), agree with the reported values of similar structure (Puviarasan et al., 1998; Wu, Xu, Zhou et al., 2005; Wu, Xu, Wan et al., 2005; Schollmeyer et al., 2005; Nissa et al., 2001). The phenyl ring makes a dihedral angle of 59.67 (4)° with the benzene ring of the chromanone unit.

The molecular structure is stabilized by a weak intramolecular C—H···O interaction and the crystal packing is stabilized by a weak intermolecular C—H···O hydrogen bond and C—H···π interactions involving the phenyl C1—C6 ring and the benzene C10/C11/C15—C17/C13 ring.

Related literature top

For related literature, see: Puviarasan et al. (1998); Tillekeratne et al. (2001); Nissa et al. (2001); Kang et al. (2004); Wu, Xu, Zhou et al. (2005); Wu, Xu, Wan et al. (2005); Schollmeyer et al. (2005). A similar methoxychroman-4-one compound has been reported recently (Suresh et al., 2007).

Experimental top

Reaction was carried out in 10 mmol scale of bromomethylpropenoate with 2-methoxy-4-methyl phenol in the presence of potassium carbonate in acetone at reflux temperature for 3 h. Then the pure ester 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 precipitate was purified by recrystalization. Finally the acid was treated with TFAA and the reaction mixture refluxed in dichloromethane for 1 h. It was further purified by column chromatography (silica gel, 3% EtOAc- hexane).

Refinement top

H atoms were positioned geometrically (C—H = 0.95 - 0.99 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

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 (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
3-Benzylidene-8-methoxy-6-methylchroman-4-one top
Crystal data top
C18H16O3F(000) = 592
Mr = 280.31Dx = 1.340 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yabCell parameters from 20682 reflections
a = 13.0081 (9) Åθ = 1.6–28.8°
b = 8.1407 (5) ŵ = 0.09 mm1
c = 13.758 (1) ÅT = 150 K
β = 107.522 (5)°Plate, yellow
V = 1389.31 (16) Å30.44 × 0.29 × 0.06 mm
Z = 4
Data collection top
Stoe IPDS2
diffractometer
3551 independent reflections
Radiation source: fine-focus sealed tube2574 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
Detector resolution: 6.67 pixels mm-1θmax = 28.7°, θmin = 2.9°
ω scansh = 1717
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 1010
Tmin = 0.988, Tmax = 0.991l = 1818
15939 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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0515P)2 + 0.065P]
where P = (Fo2 + 2Fc2)/3
3551 reflections(Δ/σ)max = 0.001
192 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C18H16O3V = 1389.31 (16) Å3
Mr = 280.31Z = 4
Monoclinic, P21/aMo Kα radiation
a = 13.0081 (9) ŵ = 0.09 mm1
b = 8.1407 (5) ÅT = 150 K
c = 13.758 (1) Å0.44 × 0.29 × 0.06 mm
β = 107.522 (5)°
Data collection top
Stoe IPDS2
diffractometer
3551 independent reflections
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
2574 reflections with I > 2σ(I)
Tmin = 0.988, Tmax = 0.991Rint = 0.055
15939 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.099H-atom parameters constrained
S = 1.03Δρmax = 0.22 e Å3
3551 reflectionsΔρmin = 0.15 e Å3
192 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
O10.78602 (7)0.02990 (10)0.02502 (6)0.0269 (2)
O30.75897 (7)0.05559 (10)0.17011 (7)0.0281 (2)
O21.02517 (7)0.25015 (11)0.21383 (7)0.0316 (2)
C170.89940 (10)0.14732 (14)0.16166 (9)0.0259 (3)
H170.89070.13710.23250.031*
C110.92597 (9)0.17538 (14)0.04513 (9)0.0240 (2)
C130.83512 (10)0.05403 (14)0.11889 (9)0.0243 (2)
C100.84867 (9)0.06858 (13)0.01381 (9)0.0234 (2)
C80.87402 (10)0.07504 (14)0.19619 (9)0.0249 (2)
C140.73210 (12)0.05403 (17)0.27867 (10)0.0349 (3)
H14A0.79340.09500.29910.052*
H14B0.66930.12460.30780.052*
H14C0.71520.05850.30360.052*
C160.97710 (10)0.25671 (14)0.10298 (10)0.0263 (3)
C120.94866 (10)0.17583 (14)0.15659 (9)0.0249 (2)
C10.84397 (10)0.05118 (15)0.35372 (9)0.0273 (3)
C70.90426 (10)0.03749 (15)0.29547 (10)0.0271 (3)
H70.97440.07310.33350.033*
C150.98897 (10)0.27015 (14)0.00074 (10)0.0262 (3)
H151.04060.34470.03970.031*
C60.73213 (11)0.03713 (16)0.33350 (10)0.0301 (3)
H60.69170.03000.27880.036*
C20.90143 (12)0.14728 (16)0.43647 (10)0.0332 (3)
H20.97760.15510.45270.040*
C90.77010 (10)0.02889 (16)0.11825 (10)0.0276 (3)
H9A0.72200.12590.10300.033*
H9B0.73410.05760.14670.033*
C40.73819 (13)0.21907 (18)0.47312 (11)0.0389 (3)
H40.70200.27780.51280.047*
C50.68008 (12)0.12118 (18)0.39318 (10)0.0350 (3)
H50.60420.11130.37900.042*
C181.04741 (11)0.35413 (16)0.15150 (11)0.0329 (3)
H18A1.10900.39910.09820.049*
H18B1.07340.28230.19620.049*
H18C1.00540.44430.19160.049*
C30.84876 (13)0.23136 (18)0.49522 (11)0.0393 (3)
H30.88880.29740.55070.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0305 (5)0.0265 (4)0.0239 (4)0.0063 (3)0.0085 (4)0.0005 (3)
O30.0337 (5)0.0253 (4)0.0241 (4)0.0048 (4)0.0071 (4)0.0018 (3)
O20.0315 (5)0.0287 (4)0.0308 (5)0.0055 (4)0.0038 (4)0.0012 (4)
C170.0287 (6)0.0230 (5)0.0265 (6)0.0041 (5)0.0090 (5)0.0040 (4)
C110.0241 (6)0.0195 (5)0.0273 (6)0.0023 (4)0.0063 (5)0.0013 (4)
C130.0261 (6)0.0189 (5)0.0267 (6)0.0016 (4)0.0062 (5)0.0004 (4)
C100.0247 (6)0.0188 (5)0.0269 (6)0.0017 (4)0.0080 (5)0.0030 (4)
C80.0264 (6)0.0208 (5)0.0274 (6)0.0010 (4)0.0080 (5)0.0011 (4)
C140.0438 (8)0.0331 (7)0.0247 (7)0.0067 (6)0.0057 (6)0.0003 (5)
C160.0261 (6)0.0206 (5)0.0329 (7)0.0036 (5)0.0098 (5)0.0057 (5)
C120.0251 (6)0.0205 (5)0.0271 (6)0.0012 (4)0.0048 (5)0.0000 (4)
C10.0353 (7)0.0238 (6)0.0221 (6)0.0022 (5)0.0076 (5)0.0037 (5)
C70.0289 (6)0.0240 (6)0.0269 (6)0.0001 (5)0.0061 (5)0.0017 (5)
C150.0240 (6)0.0201 (5)0.0329 (7)0.0004 (4)0.0063 (5)0.0015 (5)
C60.0373 (7)0.0289 (6)0.0241 (6)0.0014 (5)0.0094 (5)0.0038 (5)
C20.0377 (7)0.0311 (7)0.0275 (7)0.0031 (5)0.0048 (5)0.0001 (5)
C90.0278 (6)0.0303 (6)0.0254 (6)0.0030 (5)0.0089 (5)0.0012 (5)
C40.0536 (9)0.0375 (7)0.0278 (7)0.0134 (6)0.0155 (7)0.0021 (6)
C50.0402 (8)0.0383 (7)0.0285 (7)0.0076 (6)0.0134 (6)0.0069 (6)
C180.0351 (7)0.0285 (6)0.0371 (7)0.0025 (5)0.0139 (6)0.0052 (5)
C30.0529 (9)0.0349 (7)0.0256 (7)0.0066 (6)0.0052 (6)0.0048 (5)
Geometric parameters (Å, º) top
O1—C101.3617 (14)C1—C21.3981 (18)
O1—C91.4412 (15)C1—C61.4012 (18)
O3—C131.3615 (14)C1—C71.4685 (17)
O3—C141.4280 (15)C7—H70.9500
O2—C121.2268 (15)C15—H150.9500
C17—C131.3851 (16)C6—C51.3913 (18)
C17—C161.4054 (18)C6—H60.9500
C17—H170.9500C2—C31.3873 (19)
C11—C101.3906 (16)C2—H20.9500
C11—C151.4058 (16)C9—H9A0.9900
C11—C121.4718 (17)C9—H9B0.9900
C13—C101.4076 (17)C4—C31.381 (2)
C8—C71.3381 (18)C4—C51.384 (2)
C8—C121.4937 (16)C4—H40.9500
C8—C91.4985 (18)C5—H50.9500
C14—H14A0.9800C18—H18A0.9800
C14—H14B0.9800C18—H18B0.9800
C14—H14C0.9800C18—H18C0.9800
C16—C151.3724 (18)C3—H30.9500
C16—C181.5095 (17)
C10—O1—C9114.64 (9)C8—C7—H7115.5
C13—O3—C14116.51 (9)C1—C7—H7115.5
C13—C17—C16121.68 (11)C16—C15—C11121.03 (11)
C13—C17—H17119.2C16—C15—H15119.5
C16—C17—H17119.2C11—C15—H15119.5
C10—C11—C15119.89 (11)C5—C6—C1120.22 (13)
C10—C11—C12119.48 (10)C5—C6—H6119.9
C15—C11—C12120.35 (11)C1—C6—H6119.9
O3—C13—C17125.28 (11)C3—C2—C1120.92 (13)
O3—C13—C10115.68 (10)C3—C2—H2119.5
C17—C13—C10119.03 (11)C1—C2—H2119.5
O1—C10—C11123.53 (11)O1—C9—C8112.32 (10)
O1—C10—C13116.66 (10)O1—C9—H9A109.1
C11—C10—C13119.76 (10)C8—C9—H9A109.1
C7—C8—C12118.31 (11)O1—C9—H9B109.1
C7—C8—C9126.72 (11)C8—C9—H9B109.1
C12—C8—C9114.97 (10)H9A—C9—H9B107.9
O3—C14—H14A109.5C3—C4—C5120.00 (13)
O3—C14—H14B109.5C3—C4—H4120.0
H14A—C14—H14B109.5C5—C4—H4120.0
O3—C14—H14C109.5C4—C5—C6120.39 (14)
H14A—C14—H14C109.5C4—C5—H5119.8
H14B—C14—H14C109.5C6—C5—H5119.8
C15—C16—C17118.60 (11)C16—C18—H18A109.5
C15—C16—C18121.01 (12)C16—C18—H18B109.5
C17—C16—C18120.37 (11)H18A—C18—H18B109.5
O2—C12—C11122.65 (11)C16—C18—H18C109.5
O2—C12—C8121.84 (11)H18A—C18—H18C109.5
C11—C12—C8115.48 (10)H18B—C18—H18C109.5
C2—C1—C6118.42 (12)C4—C3—C2120.01 (13)
C2—C1—C7118.49 (12)C4—C3—H3120.0
C6—C1—C7123.00 (12)C2—C3—H3120.0
C8—C7—C1128.91 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O20.952.432.7922 (15)103
C18—H18C···O2i0.982.523.3937 (16)148
C9—H9B···Cg1ii0.992.993.7499 (14)135
C14—H14C···Cg2iii0.982.913.8592 (15)162
Symmetry codes: (i) x+2, y1, z; (ii) x+3/2, y+1/2, z; (iii) x+3/2, y1/2, z.

Experimental details

Crystal data
Chemical formulaC18H16O3
Mr280.31
Crystal system, space groupMonoclinic, P21/a
Temperature (K)150
a, b, c (Å)13.0081 (9), 8.1407 (5), 13.758 (1)
β (°) 107.522 (5)
V3)1389.31 (16)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.44 × 0.29 × 0.06
Data collection
DiffractometerStoe IPDS2
diffractometer
Absorption correctionIntegration
(X-RED; Stoe & Cie, 2002)
Tmin, Tmax0.988, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
15939, 3551, 2574
Rint0.055
(sin θ/λ)max1)0.676
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.099, 1.03
No. of reflections3551
No. of parameters192
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.15

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···O20.952.432.7922 (15)103
C18—H18C···O2i0.982.523.3937 (16)148
C9—H9B···Cg1ii0.992.993.7499 (14)135
C14—H14C···Cg2iii0.982.913.8592 (15)162
Symmetry codes: (i) x+2, y1, z; (ii) x+3/2, y+1/2, z; (iii) x+3/2, y1/2, z.
 

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