organic compounds
The molecular structure of the title compound, C11H10O4, contains two fused six-membered rings. All non-H atoms are constrained to be coplanar by symmetry, the molecule lying in a mirror plane.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053803/bh2068sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053803/bh2068Isup2.hkl |
CCDC reference: 633604
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.032
- wR factor = 0.090
- Data-to-parameter ratio = 8.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 8.53 PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C10 .. 3.00 Ang.
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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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).
5,7-Dimethoxy-2H-chromen-2-one top
Crystal data top
C11H10O4 | Dx = 1.422 Mg m−3 |
Mr = 206.19 | Melting point = 421–423 K |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 25 reflections |
a = 10.518 (3) Å | θ = 3.0–27.5° |
b = 6.706 (2) Å | µ = 0.11 mm−1 |
c = 13.652 (6) Å | T = 298 K |
V = 962.9 (6) Å3 | Chunk, colourless |
Z = 4 | 0.26 × 0.21 × 0.14 mm |
F(000) = 432 |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 704 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 25.2°, θmin = 3.0° |
ω/2θ scans | h = −12→0 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = 0→8 |
Tmin = 0.928, Tmax = 0.979 | l = −1→16 |
1021 measured reflections | 3 standard reflections every 60 min |
938 independent reflections | intensity decay: 0.3% |
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)] = 0.032 | Only H-atom coordinates refined |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0424P)2 + 0.1836P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
938 reflections | Δρmax = 0.19 e Å−3 |
110 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.038 (6) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.77824 (12) | 0.2500 | 0.50449 (10) | 0.0460 (4) | |
O2 | 0.62281 (14) | 0.2500 | 0.39770 (13) | 0.0763 (7) | |
O3 | 1.21138 (13) | 0.2500 | 0.41131 (10) | 0.0529 (5) | |
O4 | 1.10359 (14) | 0.2500 | 0.74683 (11) | 0.0532 (5) | |
C1 | 1.0597 (2) | 0.2500 | 0.65329 (16) | 0.0411 (5) | |
C2 | 1.15577 (19) | 0.2500 | 0.58222 (15) | 0.0417 (5) | |
C3 | 1.12518 (19) | 0.2500 | 0.48502 (15) | 0.0386 (5) | |
C4 | 0.9553 (2) | 0.2500 | 0.35510 (16) | 0.0426 (5) | |
C5 | 0.8312 (2) | 0.2500 | 0.33380 (17) | 0.0492 (6) | |
C6 | 0.7368 (2) | 0.2500 | 0.40872 (17) | 0.0488 (6) | |
C7 | 0.9331 (2) | 0.2500 | 0.62717 (15) | 0.0414 (5) | |
C8 | 0.90584 (18) | 0.2500 | 0.52798 (15) | 0.0374 (5) | |
C9 | 0.99642 (17) | 0.2500 | 0.45456 (15) | 0.0366 (5) | |
C10 | 1.3428 (2) | 0.2500 | 0.4386 (2) | 0.0632 (8) | |
C11 | 1.0121 (3) | 0.2500 | 0.82405 (19) | 0.0620 (7) | |
H2 | 1.241 (3) | 0.2500 | 0.606 (2) | 0.074* | |
H4 | 1.018 (3) | 0.2500 | 0.304 (2) | 0.074* | |
H5 | 0.802 (2) | 0.2500 | 0.268 (2) | 0.074* | |
H7 | 0.866 (2) | 0.2500 | 0.675 (2) | 0.074* | |
H10A | 1.3617 (16) | 0.134 (3) | 0.4793 (13) | 0.074* | |
H10B | 1.389 (2) | 0.2500 | 0.378 (2) | 0.074* | |
H11A | 0.9542 (16) | 0.131 (3) | 0.8169 (13) | 0.074* | |
H11B | 1.063 (3) | 0.2500 | 0.883 (2) | 0.074* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0253 (8) | 0.0620 (10) | 0.0507 (9) | 0.000 | −0.0001 (6) | 0.000 |
O2 | 0.0283 (9) | 0.1245 (17) | 0.0762 (12) | 0.000 | −0.0114 (8) | 0.000 |
O3 | 0.0260 (7) | 0.0894 (12) | 0.0435 (9) | 0.000 | 0.0044 (6) | 0.000 |
O4 | 0.0468 (9) | 0.0753 (11) | 0.0374 (8) | 0.000 | −0.0038 (7) | 0.000 |
C1 | 0.0400 (12) | 0.0441 (12) | 0.0392 (11) | 0.000 | −0.0020 (9) | 0.000 |
C2 | 0.0279 (11) | 0.0502 (13) | 0.0469 (12) | 0.000 | −0.0028 (10) | 0.000 |
C3 | 0.0293 (11) | 0.0445 (12) | 0.0421 (11) | 0.000 | 0.0031 (9) | 0.000 |
C4 | 0.0354 (12) | 0.0502 (13) | 0.0421 (12) | 0.000 | 0.0019 (10) | 0.000 |
C5 | 0.0419 (13) | 0.0602 (15) | 0.0456 (12) | 0.000 | −0.0078 (10) | 0.000 |
C6 | 0.0323 (11) | 0.0583 (14) | 0.0558 (14) | 0.000 | −0.0074 (10) | 0.000 |
C7 | 0.0345 (11) | 0.0470 (13) | 0.0426 (12) | 0.000 | 0.0056 (9) | 0.000 |
C8 | 0.0249 (10) | 0.0404 (12) | 0.0469 (12) | 0.000 | 0.0005 (9) | 0.000 |
C9 | 0.0292 (11) | 0.0379 (11) | 0.0425 (11) | 0.000 | −0.0012 (8) | 0.000 |
C10 | 0.0282 (12) | 0.109 (2) | 0.0527 (15) | 0.000 | 0.0041 (10) | 0.000 |
C11 | 0.0597 (17) | 0.087 (2) | 0.0392 (13) | 0.000 | 0.0024 (12) | 0.000 |
Geometric parameters (Å, º) top
O1—C6 | 1.378 (3) | C4—C5 | 1.338 (3) |
O1—C8 | 1.380 (2) | C4—C9 | 1.425 (3) |
O2—C6 | 1.208 (3) | C4—H4 | 0.96 (3) |
O3—C3 | 1.354 (2) | C5—C6 | 1.426 (3) |
O3—C10 | 1.432 (3) | C5—H5 | 0.95 (3) |
O4—C1 | 1.358 (3) | C7—C8 | 1.384 (3) |
O4—C11 | 1.427 (3) | C7—H7 | 0.96 (3) |
C1—C7 | 1.379 (3) | C8—C9 | 1.383 (3) |
C1—C2 | 1.401 (3) | C10—H10A | 0.977 (18) |
C2—C3 | 1.366 (3) | C10—H10B | 0.96 (3) |
C2—H2 | 0.95 (3) | C11—H11A | 1.010 (18) |
C3—C9 | 1.417 (3) | C11—H11B | 0.97 (3) |
C6—O1—C8 | 121.89 (16) | O2—C6—O1 | 115.6 (2) |
C3—O3—C10 | 116.94 (17) | O2—C6—C5 | 127.0 (2) |
C1—O4—C11 | 117.74 (18) | O1—C6—C5 | 117.39 (19) |
O4—C1—C7 | 124.9 (2) | C1—C7—C8 | 116.9 (2) |
O4—C1—C2 | 113.95 (18) | C1—C7—H7 | 122.6 (16) |
C7—C1—C2 | 121.2 (2) | C8—C7—H7 | 120.5 (16) |
C3—C2—C1 | 120.20 (19) | O1—C8—C9 | 120.10 (18) |
C3—C2—H2 | 123.3 (17) | O1—C8—C7 | 115.39 (18) |
C1—C2—H2 | 116.5 (17) | C9—C8—C7 | 124.51 (19) |
O3—C3—C2 | 124.35 (19) | C8—C9—C3 | 116.48 (19) |
O3—C3—C9 | 114.95 (18) | C8—C9—C4 | 118.80 (19) |
C2—C3—C9 | 120.70 (19) | C3—C9—C4 | 124.72 (19) |
C5—C4—C9 | 120.2 (2) | O3—C10—H10A | 110.1 (11) |
C5—C4—H4 | 121.1 (16) | O3—C10—H10B | 105.1 (15) |
C9—C4—H4 | 118.7 (16) | H10A—C10—H10B | 112.9 (13) |
C4—C5—C6 | 121.6 (2) | O4—C11—H11A | 109.6 (10) |
C4—C5—H5 | 121.2 (16) | O4—C11—H11B | 104.3 (17) |
C6—C5—H5 | 117.2 (16) | H11A—C11—H11B | 114.3 (13) |
C11—O4—C1—C7 | 0.0 | C6—O1—C8—C9 | 0.0 |
C11—O4—C1—C2 | 180.0 | C6—O1—C8—C7 | 180.0 |
O4—C1—C2—C3 | 180.0 | C1—C7—C8—O1 | 180.0 |
C7—C1—C2—C3 | 0.0 | C1—C7—C8—C9 | 0.0 |
C10—O3—C3—C2 | 0.0 | O1—C8—C9—C3 | 180.0 |
C10—O3—C3—C9 | 180.0 | C7—C8—C9—C3 | 0.0 |
C1—C2—C3—O3 | 180.0 | O1—C8—C9—C4 | 0.0 |
C1—C2—C3—C9 | 0.0 | C7—C8—C9—C4 | 180.0 |
C9—C4—C5—C6 | 0.0 | O3—C3—C9—C8 | 180.0 |
C8—O1—C6—O2 | 180.0 | C2—C3—C9—C8 | 0.0 |
C8—O1—C6—C5 | 0.0 | O3—C3—C9—C4 | 0.0 |
C4—C5—C6—O2 | 180.0 | C2—C3—C9—C4 | 180.0 |
C4—C5—C6—O1 | 0.0 | C5—C4—C9—C8 | 0.0 |
O4—C1—C7—C8 | 180.0 | C5—C4—C9—C3 | 180.0 |
C2—C1—C7—C8 | 0.0 |