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In the title compound, C12H12O3, the heterocyclic ring adopts a half-chair conformation. C–H...O hydrogen bonds form a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006320/dn2126sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006320/dn2126Isup2.hkl
Contains datablock I

CCDC reference: 640315

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.053
  • wR factor = 0.169
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H13A .. O3 .. 2.66 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 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 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

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

rac-4-Methoxy-6-phenyl-5,6-dihydro-2-pyrone top
Crystal data top
C12H12O3F(000) = 432
Mr = 204.22Dx = 1.321 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2364 reflections
a = 5.669 (2) Åθ = 1.9–27.5°
b = 9.516 (3) ŵ = 0.10 mm1
c = 19.091 (4) ÅT = 293 K
β = 94.49 (3)°Prism, colourless
V = 1026.7 (5) Å30.25 × 0.20 × 0.15 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
1436 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590Rint = 0.038
Horizonally mounted graphite crystal monochromatorθmax = 27.5°, θmin = 2.4°
Detector resolution: 9 pixels mm-1h = 77
φ? ω? scansk = 1211
4386 measured reflectionsl = 2424
2334 independent 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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0854P)2]
where P = (Fo2 + 2Fc2)/3
2334 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.31 e Å3
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
O11.0872 (2)0.56057 (13)0.13379 (7)0.0525 (4)
O21.3115 (3)0.64806 (15)0.05567 (9)0.0637 (5)
O31.0857 (3)0.17208 (14)0.03831 (8)0.0592 (4)
C21.2229 (3)0.5439 (2)0.07862 (11)0.0499 (5)
C31.2444 (3)0.4041 (2)0.04927 (11)0.0511 (5)
H31.35720.38670.01750.061*
C41.1032 (3)0.3004 (2)0.06758 (11)0.0496 (5)
C50.9407 (4)0.3202 (2)0.12429 (12)0.0550 (5)
H5A0.92850.23330.15030.066*
H5B0.78410.34490.10390.066*
C61.0344 (3)0.4360 (2)0.17348 (11)0.0501 (5)
H61.18150.40310.19860.060*
C70.8658 (3)0.4772 (2)0.22671 (10)0.0481 (5)
C80.8750 (4)0.4073 (2)0.29065 (12)0.0583 (6)
H80.99060.33930.30070.070*
C90.7158 (4)0.4369 (3)0.33944 (12)0.0663 (6)
H90.72260.38810.38170.080*
C100.5468 (4)0.5387 (3)0.32558 (12)0.0641 (6)
H100.43980.55940.35870.077*
C110.5359 (4)0.6098 (3)0.26298 (13)0.0635 (6)
H110.42220.67930.25380.076*
C120.6933 (3)0.5788 (2)0.21332 (12)0.0570 (6)
H120.68320.62640.17070.068*
C131.2277 (4)0.1445 (3)0.01912 (14)0.0716 (7)
H13A1.19930.05040.03570.107*
H13B1.39190.15510.00360.107*
H13C1.18680.20970.05650.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0612 (8)0.0451 (8)0.0528 (8)0.0094 (6)0.0148 (7)0.0013 (6)
O30.0741 (9)0.0434 (8)0.0619 (9)0.0097 (6)0.0164 (8)0.0072 (7)
O20.0741 (9)0.0498 (9)0.0697 (10)0.0189 (7)0.0204 (8)0.0023 (7)
C40.0535 (11)0.0428 (11)0.0525 (12)0.0042 (8)0.0037 (9)0.0011 (9)
C70.0480 (10)0.0462 (11)0.0503 (11)0.0064 (8)0.0056 (8)0.0004 (9)
C20.0494 (10)0.0511 (11)0.0496 (11)0.0088 (8)0.0065 (9)0.0017 (9)
C60.0521 (10)0.0465 (11)0.0524 (12)0.0055 (8)0.0078 (9)0.0036 (9)
C30.0511 (10)0.0496 (12)0.0537 (12)0.0061 (8)0.0107 (9)0.0028 (9)
C80.0682 (12)0.0531 (12)0.0541 (13)0.0075 (9)0.0073 (10)0.0072 (10)
C120.0554 (12)0.0625 (14)0.0531 (12)0.0014 (9)0.0032 (10)0.0099 (10)
C110.0516 (11)0.0689 (14)0.0706 (16)0.0084 (10)0.0076 (11)0.0072 (12)
C50.0583 (11)0.0480 (11)0.0600 (13)0.0098 (9)0.0130 (10)0.0013 (10)
C90.0837 (16)0.0654 (15)0.0512 (13)0.0000 (12)0.0145 (12)0.0068 (11)
C130.0877 (16)0.0548 (14)0.0755 (17)0.0071 (12)0.0267 (14)0.0155 (12)
C100.0635 (12)0.0709 (15)0.0597 (14)0.0013 (11)0.0156 (11)0.0035 (12)
Geometric parameters (Å, º) top
O1—C21.361 (2)C8—C91.376 (3)
O1—C61.451 (2)C8—H80.9300
O3—C41.343 (2)C12—C111.384 (3)
O3—C131.434 (3)C12—H120.9300
O2—C21.209 (2)C11—C101.370 (3)
C4—C31.334 (3)C11—H110.9300
C4—C51.487 (3)C5—H5A0.9700
C7—C121.384 (3)C5—H5B0.9700
C7—C81.388 (3)C9—C101.374 (3)
C7—C61.501 (3)C9—H90.9300
C2—C31.452 (3)C13—H13A0.9600
C6—C51.517 (3)C13—H13B0.9600
C6—H60.9800C13—H13C0.9600
C3—H30.9300C10—H100.9300
C2—O1—C6117.44 (15)C7—C12—H12119.8
C4—O3—C13117.17 (15)C11—C12—H12119.8
C3—C4—O3126.11 (18)C10—C11—C12120.3 (2)
C3—C4—C5121.04 (18)C10—C11—H11119.9
O3—C4—C5112.84 (16)C12—C11—H11119.9
C12—C7—C8118.34 (18)C4—C5—C6109.62 (16)
C12—C7—C6122.39 (18)C4—C5—H5A109.7
C8—C7—C6119.21 (19)C6—C5—H5A109.7
O2—C2—O1117.43 (18)C4—C5—H5B109.7
O2—C2—C3124.16 (18)C6—C5—H5B109.7
O1—C2—C3118.36 (16)H5A—C5—H5B108.2
O1—C6—C7107.95 (16)C10—C9—C8119.9 (2)
O1—C6—C5110.29 (17)C10—C9—H9120.0
C7—C6—C5113.46 (15)C8—C9—H9120.0
O1—C6—H6108.3O3—C13—H13A109.5
C7—C6—H6108.3O3—C13—H13B109.5
C5—C6—H6108.3H13A—C13—H13B109.5
C4—C3—C2120.40 (17)O3—C13—H13C109.5
C4—C3—H3119.8H13A—C13—H13C109.5
C2—C3—H3119.8H13B—C13—H13C109.5
C9—C8—C7121.0 (2)C11—C10—C9120.0 (2)
C9—C8—H8119.5C11—C10—H10120.0
C7—C8—H8119.5C9—C10—H10120.0
C7—C12—C11120.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.932.453.375 (3)173
C9—H9···O2ii0.932.593.411 (3)147
C13—H13A···O3iii0.962.663.502 (3)147
Symmetry codes: (i) x+3, y+1, z; (ii) x+2, y1/2, z+1/2; (iii) x+2, y, z.
 

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