In the title compound, C
12H
12O
3, the heterocyclic ring adopts a half-chair conformation. C–H
O hydrogen bonds form a three-dimensional network.
Supporting information
CCDC reference: 640315
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C12H12O3 | F(000) = 432 |
Mr = 204.22 | Dx = 1.321 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2364 reflections |
a = 5.669 (2) Å | θ = 1.9–27.5° |
b = 9.516 (3) Å | µ = 0.10 mm−1 |
c = 19.091 (4) Å | T = 293 K |
β = 94.49 (3)° | Prism, colourless |
V = 1026.7 (5) Å3 | 0.25 × 0.20 × 0.15 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 1436 reflections with I > 2σ(I) |
Radiation source: Enraf–Nonius FR590 | Rint = 0.038 |
Horizonally mounted graphite crystal monochromator | θmax = 27.5°, θmin = 2.4° |
Detector resolution: 9 pixels mm-1 | h = −7→7 |
φ? ω? scans | k = −12→11 |
4386 measured reflections | l = −24→24 |
2334 independent reflections | |
Refinement top
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.169 | H-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 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 1.0872 (2) | 0.56057 (13) | 0.13379 (7) | 0.0525 (4) | |
O2 | 1.3115 (3) | 0.64806 (15) | 0.05567 (9) | 0.0637 (5) | |
O3 | 1.0857 (3) | 0.17208 (14) | 0.03831 (8) | 0.0592 (4) | |
C2 | 1.2229 (3) | 0.5439 (2) | 0.07862 (11) | 0.0499 (5) | |
C3 | 1.2444 (3) | 0.4041 (2) | 0.04927 (11) | 0.0511 (5) | |
H3 | 1.3572 | 0.3867 | 0.0175 | 0.061* | |
C4 | 1.1032 (3) | 0.3004 (2) | 0.06758 (11) | 0.0496 (5) | |
C5 | 0.9407 (4) | 0.3202 (2) | 0.12429 (12) | 0.0550 (5) | |
H5A | 0.9285 | 0.2333 | 0.1503 | 0.066* | |
H5B | 0.7841 | 0.3449 | 0.1039 | 0.066* | |
C6 | 1.0344 (3) | 0.4360 (2) | 0.17348 (11) | 0.0501 (5) | |
H6 | 1.1815 | 0.4031 | 0.1986 | 0.060* | |
C7 | 0.8658 (3) | 0.4772 (2) | 0.22671 (10) | 0.0481 (5) | |
C8 | 0.8750 (4) | 0.4073 (2) | 0.29065 (12) | 0.0583 (6) | |
H8 | 0.9906 | 0.3393 | 0.3007 | 0.070* | |
C9 | 0.7158 (4) | 0.4369 (3) | 0.33944 (12) | 0.0663 (6) | |
H9 | 0.7226 | 0.3881 | 0.3817 | 0.080* | |
C10 | 0.5468 (4) | 0.5387 (3) | 0.32558 (12) | 0.0641 (6) | |
H10 | 0.4398 | 0.5594 | 0.3587 | 0.077* | |
C11 | 0.5359 (4) | 0.6098 (3) | 0.26298 (13) | 0.0635 (6) | |
H11 | 0.4222 | 0.6793 | 0.2538 | 0.076* | |
C12 | 0.6933 (3) | 0.5788 (2) | 0.21332 (12) | 0.0570 (6) | |
H12 | 0.6832 | 0.6264 | 0.1707 | 0.068* | |
C13 | 1.2277 (4) | 0.1445 (3) | −0.01912 (14) | 0.0716 (7) | |
H13A | 1.1993 | 0.0504 | −0.0357 | 0.107* | |
H13B | 1.3919 | 0.1551 | −0.0036 | 0.107* | |
H13C | 1.1868 | 0.2097 | −0.0565 | 0.107* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0612 (8) | 0.0451 (8) | 0.0528 (8) | −0.0094 (6) | 0.0148 (7) | −0.0013 (6) |
O3 | 0.0741 (9) | 0.0434 (8) | 0.0619 (9) | −0.0097 (6) | 0.0164 (8) | −0.0072 (7) |
O2 | 0.0741 (9) | 0.0498 (9) | 0.0697 (10) | −0.0189 (7) | 0.0204 (8) | −0.0023 (7) |
C4 | 0.0535 (11) | 0.0428 (11) | 0.0525 (12) | −0.0042 (8) | 0.0037 (9) | −0.0011 (9) |
C7 | 0.0480 (10) | 0.0462 (11) | 0.0503 (11) | −0.0064 (8) | 0.0056 (8) | −0.0004 (9) |
C2 | 0.0494 (10) | 0.0511 (11) | 0.0496 (11) | −0.0088 (8) | 0.0065 (9) | −0.0017 (9) |
C6 | 0.0521 (10) | 0.0465 (11) | 0.0524 (12) | −0.0055 (8) | 0.0078 (9) | 0.0036 (9) |
C3 | 0.0511 (10) | 0.0496 (12) | 0.0537 (12) | −0.0061 (8) | 0.0107 (9) | −0.0028 (9) |
C8 | 0.0682 (12) | 0.0531 (12) | 0.0541 (13) | 0.0075 (9) | 0.0073 (10) | 0.0072 (10) |
C12 | 0.0554 (12) | 0.0625 (14) | 0.0531 (12) | −0.0014 (9) | 0.0032 (10) | 0.0099 (10) |
C11 | 0.0516 (11) | 0.0689 (14) | 0.0706 (16) | 0.0084 (10) | 0.0076 (11) | 0.0072 (12) |
C5 | 0.0583 (11) | 0.0480 (11) | 0.0600 (13) | −0.0098 (9) | 0.0130 (10) | −0.0013 (10) |
C9 | 0.0837 (16) | 0.0654 (15) | 0.0512 (13) | 0.0000 (12) | 0.0145 (12) | 0.0068 (11) |
C13 | 0.0877 (16) | 0.0548 (14) | 0.0755 (17) | −0.0071 (12) | 0.0267 (14) | −0.0155 (12) |
C10 | 0.0635 (12) | 0.0709 (15) | 0.0597 (14) | 0.0013 (11) | 0.0156 (11) | −0.0035 (12) |
Geometric parameters (Å, º) top
O1—C2 | 1.361 (2) | C8—C9 | 1.376 (3) |
O1—C6 | 1.451 (2) | C8—H8 | 0.9300 |
O3—C4 | 1.343 (2) | C12—C11 | 1.384 (3) |
O3—C13 | 1.434 (3) | C12—H12 | 0.9300 |
O2—C2 | 1.209 (2) | C11—C10 | 1.370 (3) |
C4—C3 | 1.334 (3) | C11—H11 | 0.9300 |
C4—C5 | 1.487 (3) | C5—H5A | 0.9700 |
C7—C12 | 1.384 (3) | C5—H5B | 0.9700 |
C7—C8 | 1.388 (3) | C9—C10 | 1.374 (3) |
C7—C6 | 1.501 (3) | C9—H9 | 0.9300 |
C2—C3 | 1.452 (3) | C13—H13A | 0.9600 |
C6—C5 | 1.517 (3) | C13—H13B | 0.9600 |
C6—H6 | 0.9800 | C13—H13C | 0.9600 |
C3—H3 | 0.9300 | C10—H10 | 0.9300 |
| | | |
C2—O1—C6 | 117.44 (15) | C7—C12—H12 | 119.8 |
C4—O3—C13 | 117.17 (15) | C11—C12—H12 | 119.8 |
C3—C4—O3 | 126.11 (18) | C10—C11—C12 | 120.3 (2) |
C3—C4—C5 | 121.04 (18) | C10—C11—H11 | 119.9 |
O3—C4—C5 | 112.84 (16) | C12—C11—H11 | 119.9 |
C12—C7—C8 | 118.34 (18) | C4—C5—C6 | 109.62 (16) |
C12—C7—C6 | 122.39 (18) | C4—C5—H5A | 109.7 |
C8—C7—C6 | 119.21 (19) | C6—C5—H5A | 109.7 |
O2—C2—O1 | 117.43 (18) | C4—C5—H5B | 109.7 |
O2—C2—C3 | 124.16 (18) | C6—C5—H5B | 109.7 |
O1—C2—C3 | 118.36 (16) | H5A—C5—H5B | 108.2 |
O1—C6—C7 | 107.95 (16) | C10—C9—C8 | 119.9 (2) |
O1—C6—C5 | 110.29 (17) | C10—C9—H9 | 120.0 |
C7—C6—C5 | 113.46 (15) | C8—C9—H9 | 120.0 |
O1—C6—H6 | 108.3 | O3—C13—H13A | 109.5 |
C7—C6—H6 | 108.3 | O3—C13—H13B | 109.5 |
C5—C6—H6 | 108.3 | H13A—C13—H13B | 109.5 |
C4—C3—C2 | 120.40 (17) | O3—C13—H13C | 109.5 |
C4—C3—H3 | 119.8 | H13A—C13—H13C | 109.5 |
C2—C3—H3 | 119.8 | H13B—C13—H13C | 109.5 |
C9—C8—C7 | 121.0 (2) | C11—C10—C9 | 120.0 (2) |
C9—C8—H8 | 119.5 | C11—C10—H10 | 120.0 |
C7—C8—H8 | 119.5 | C9—C10—H10 | 120.0 |
C7—C12—C11 | 120.4 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.93 | 2.45 | 3.375 (3) | 173 |
C9—H9···O2ii | 0.93 | 2.59 | 3.411 (3) | 147 |
C13—H13A···O3iii | 0.96 | 2.66 | 3.502 (3) | 147 |
Symmetry codes: (i) −x+3, −y+1, −z; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+2, −y, −z. |