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The title compound, C
11H
10O
2, belongs to the class of 4-benzopyrones (also known as chromen-4-ones) with potentially diverse pharmacological activities. It was synthesized by acylation of 2-hydroxy-4-methylacetophenone with ethyl acetate in the presence of sodium hydride and subsequent cyclization by hydrochloric acid. All non-H atoms of the substituted bicyclic molecule are coplanar within 0.03 Å. C—H
O interactions [C
O = 3.272 (5) Å] link neighbouring molecules related by the 2
1 axis.
Supporting information
CCDC reference: 259118
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.054
- wR factor = 0.184
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C1
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C10
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
2,6-Dimethyl-4
H-1-benzopyran-4-one
top
Crystal data top
C11H10O2 | F(000) = 368 |
Mr = 174.19 | Dx = 1.312 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7949 reflections |
a = 5.4595 (5) Å | θ = 2.3–29.4° |
b = 10.1947 (14) Å | µ = 0.09 mm−1 |
c = 15.8862 (15) Å | T = 293 K |
β = 93.979 (8)° | Prism, colourless |
V = 882.06 (17) Å3 | 0.60 × 0.45 × 0.30 mm |
Z = 4 | |
Data collection top
Stoe IPDS-2 diffractometer | 1740 independent reflections |
Radiation source: fine-focus sealed tube | 1328 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.088 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.4° |
rotation method scans | h = −6→6 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −12→12 |
Tmin = 0.942, Tmax = 0.982 | l = −19→19 |
6705 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.184 | w = 1/[σ2(Fo2) + (0.1083P)2 + 0.0774P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max < 0.001 |
1740 reflections | Δρmax = 0.35 e Å−3 |
135 parameters | Δρmin = −0.24 e Å−3 |
6 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.093 (16) |
Special details top
Experimental. Melting points were measured with a capillary melting point apparatus (Buchi).
The 1H NMR spectra were recorded with VARIAN Mercury 400 F T-NMR
spectrophotometer, d scale (p.p.m.) from TMS. Mass spectra were measured with
Waters Micromass ZQ by using ES(+) method. |
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 | −0.2543 (2) | 0.52505 (13) | 0.10857 (8) | 0.0511 (4) | |
O2 | 0.3617 (3) | 0.68843 (16) | 0.22357 (9) | 0.0697 (5) | |
C1 | −0.3200 (4) | 0.3829 (2) | 0.22073 (15) | 0.0607 (6) | |
H1A | −0.4548 | 0.3637 | 0.1806 | 0.091* | |
H1B | −0.3821 | 0.4130 | 0.2724 | 0.091* | |
H1C | −0.2240 | 0.3050 | 0.2315 | 0.091* | |
C2 | −0.1652 (3) | 0.48550 (19) | 0.18658 (11) | 0.0485 (5) | |
C3 | 0.0386 (3) | 0.5368 (2) | 0.22472 (12) | 0.0511 (5) | |
H3 | 0.085 (4) | 0.507 (2) | 0.2785 (15) | 0.068 (6)* | |
C4 | 0.1773 (3) | 0.63785 (19) | 0.18847 (11) | 0.0485 (5) | |
C4A | 0.0809 (3) | 0.67825 (17) | 0.10306 (10) | 0.0444 (5) | |
C5 | 0.1959 (4) | 0.77291 (19) | 0.05643 (12) | 0.0513 (5) | |
H5 | 0.335 (5) | 0.811 (2) | 0.0815 (15) | 0.067 (7)* | |
C6 | 0.1052 (4) | 0.80816 (19) | −0.02364 (12) | 0.0533 (5) | |
C7 | −0.1065 (4) | 0.7456 (2) | −0.05750 (12) | 0.0571 (6) | |
H7 | −0.171 (5) | 0.773 (2) | −0.1161 (17) | 0.076 (7)* | |
C8 | −0.2242 (4) | 0.6526 (2) | −0.01345 (12) | 0.0550 (5) | |
H8 | −0.373 (4) | 0.609 (2) | −0.0343 (15) | 0.064 (6)* | |
C9 | −0.1297 (3) | 0.61906 (18) | 0.06751 (11) | 0.0451 (5) | |
C10 | 0.2281 (5) | 0.9122 (2) | −0.07349 (15) | 0.0726 (7) | |
H10A | 0.1391 | 0.9232 | −0.1273 | 0.109* | |
H10B | 0.3936 | 0.8860 | −0.0818 | 0.109* | |
H10C | 0.2299 | 0.9936 | −0.0431 | 0.109* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0468 (7) | 0.0604 (8) | 0.0450 (8) | −0.0031 (6) | −0.0054 (5) | −0.0018 (6) |
O2 | 0.0646 (9) | 0.0890 (12) | 0.0526 (9) | −0.0150 (8) | −0.0163 (7) | −0.0062 (7) |
C1 | 0.0567 (11) | 0.0621 (12) | 0.0636 (13) | 0.0009 (9) | 0.0070 (9) | 0.0046 (10) |
C2 | 0.0485 (10) | 0.0529 (10) | 0.0439 (10) | 0.0103 (8) | 0.0015 (7) | −0.0033 (8) |
C3 | 0.0512 (11) | 0.0620 (12) | 0.0392 (10) | 0.0070 (8) | −0.0028 (8) | −0.0013 (8) |
C4 | 0.0467 (10) | 0.0589 (11) | 0.0387 (9) | 0.0040 (8) | −0.0048 (7) | −0.0102 (8) |
C4A | 0.0463 (10) | 0.0497 (10) | 0.0367 (9) | 0.0053 (7) | 0.0000 (7) | −0.0100 (7) |
C5 | 0.0519 (11) | 0.0553 (11) | 0.0464 (10) | −0.0002 (9) | 0.0018 (8) | −0.0098 (8) |
C6 | 0.0599 (12) | 0.0558 (11) | 0.0448 (10) | 0.0089 (9) | 0.0096 (8) | −0.0035 (8) |
C7 | 0.0611 (12) | 0.0680 (13) | 0.0414 (10) | 0.0121 (10) | −0.0016 (8) | −0.0012 (9) |
C8 | 0.0508 (11) | 0.0694 (13) | 0.0434 (10) | 0.0011 (9) | −0.0084 (8) | −0.0045 (9) |
C9 | 0.0434 (9) | 0.0520 (10) | 0.0393 (9) | 0.0049 (7) | −0.0012 (7) | −0.0071 (7) |
C10 | 0.0918 (17) | 0.0669 (14) | 0.0604 (13) | 0.0009 (12) | 0.0145 (12) | 0.0069 (10) |
Geometric parameters (Å, º) top
O1—C2 | 1.361 (2) | C8—H8 | 0.96 (2) |
O1—C9 | 1.367 (2) | C7—C6 | 1.395 (3) |
O2—C4 | 1.230 (2) | C7—H7 | 1.01 (3) |
C2—C3 | 1.336 (3) | C6—C5 | 1.380 (3) |
C2—C1 | 1.472 (3) | C6—C10 | 1.509 (3) |
C3—C4 | 1.424 (3) | C5—H5 | 0.92 (3) |
C3—H3 | 0.93 (2) | C1—H1A | 0.9600 |
C4—C4A | 1.479 (2) | C1—H1B | 0.9600 |
C4A—C9 | 1.384 (3) | C1—H1C | 0.9600 |
C4A—C5 | 1.392 (3) | C10—H10A | 0.9600 |
C9—C8 | 1.395 (3) | C10—H10B | 0.9600 |
C8—C7 | 1.365 (3) | C10—H10C | 0.9600 |
| | | |
C2—O1—C9 | 118.97 (14) | C8—C7—H7 | 121.2 (14) |
C3—C2—O1 | 122.06 (18) | C6—C7—H7 | 117.0 (14) |
C3—C2—C1 | 126.33 (18) | C5—C6—C7 | 118.08 (19) |
O1—C2—C1 | 111.61 (16) | C5—C6—C10 | 121.5 (2) |
C2—C3—C4 | 123.32 (18) | C7—C6—C10 | 120.39 (19) |
C2—C3—H3 | 117.2 (15) | C6—C5—C4A | 121.65 (19) |
C4—C3—H3 | 119.4 (15) | C6—C5—H5 | 121.4 (15) |
O2—C4—C3 | 124.17 (17) | C4A—C5—H5 | 117.0 (15) |
O2—C4—C4A | 121.80 (19) | C2—C1—H1A | 109.5 |
C3—C4—C4A | 114.03 (16) | C2—C1—H1B | 109.5 |
C9—C4A—C5 | 118.53 (17) | H1A—C1—H1B | 109.5 |
C9—C4A—C4 | 119.04 (17) | C2—C1—H1C | 109.5 |
C5—C4A—C4 | 122.42 (17) | H1A—C1—H1C | 109.5 |
O1—C9—C4A | 122.53 (16) | H1B—C1—H1C | 109.5 |
O1—C9—C8 | 116.61 (16) | C6—C10—H10A | 109.5 |
C4A—C9—C8 | 120.86 (18) | C6—C10—H10B | 109.5 |
C7—C8—C9 | 119.09 (18) | H10A—C10—H10B | 109.5 |
C7—C8—H8 | 124.2 (14) | C6—C10—H10C | 109.5 |
C9—C8—H8 | 116.7 (14) | H10A—C10—H10C | 109.5 |
C8—C7—C6 | 121.79 (18) | H10B—C10—H10C | 109.5 |
| | | |
C9—O1—C2—C3 | 0.8 (3) | C4—C4A—C9—O1 | 0.6 (3) |
C9—O1—C2—C1 | −179.22 (14) | C5—C4A—C9—C8 | 0.4 (3) |
O1—C2—C3—C4 | 1.2 (3) | C4—C4A—C9—C8 | −178.86 (16) |
C1—C2—C3—C4 | −178.82 (17) | O1—C9—C8—C7 | −179.71 (16) |
C2—C3—C4—O2 | 178.10 (19) | C4A—C9—C8—C7 | −0.2 (3) |
C2—C3—C4—C4A | −2.1 (3) | C9—C8—C7—C6 | −0.2 (3) |
O2—C4—C4A—C9 | −178.97 (17) | C8—C7—C6—C5 | 0.5 (3) |
C3—C4—C4A—C9 | 1.2 (2) | C8—C7—C6—C10 | −178.89 (18) |
O2—C4—C4A—C5 | 1.8 (3) | C7—C6—C5—C4A | −0.3 (3) |
C3—C4—C4A—C5 | −178.03 (16) | C10—C6—C5—C4A | 179.07 (17) |
C2—O1—C9—C4A | −1.6 (2) | C9—C4A—C5—C6 | −0.2 (3) |
C2—O1—C9—C8 | 177.81 (16) | C4—C4A—C5—C6 | 179.11 (17) |
C5—C4A—C9—O1 | 179.86 (15) | | |
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