Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802016136/cf6205sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802016136/cf6205Isup2.hkl |
CCDC reference: 198962
Key indicators
- Single-crystal X-ray study
- T = 183 K
- Mean (C-C) = 0.002 Å
- R factor = 0.049
- wR factor = 0.144
- Data-to-parameter ratio = 16.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The synthesis of 1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-3-(4- methoxyphenyl)-2-methyl-1,3-propanedione, (I), has been described by Gaillard et al. (1996), who also published 1H-NMR data for the substance. Crystals suitable for X-ray analysis were obtained from benzene (m.p. 445–446 K).
Initial efinement of the structure converged with unacceptably high R-values (R = 0.095 for observed reflections and wR2 = 0.306 for all reflections), and there were seven residual peaks in the electron density difference map larger than 0.42 e Å−3 (maximum 1.64 e Å−3). These peaks appeared close to the 4-methoxyphenyl group and indicated disorder. Six of the seven largest peaks formed a planar ring and they were taken to be the phenyl carbon atoms, while the largest residual peak could be attributed to the methoxy oxygen atom. The methoxy carbon atom was also found (peak height 0.26 e Å−3). No other atom, except the benzylic carbon atom attached to the 4-methoxyphenyl group, could be resolved into two parts. Another kind of disorder was found in the methyl group C10. Refinement with geometrical similarity restraints on disordered atoms led to occupancies of 0.806:0.194 (3).
Hydrogen atoms were refined isotropically and were constrained to the ideal geometry, using an appropriate riding model. For the hydroxyl group, the O–H distance (0.84 Å) and C–O–H angle (109.5°) were kept fixed, and the torsion angle was chosen to match the observed electron density. For methyl groups, the C–H distances (0.96 Å) and C–C–H angles (109.5°) were kept fixed, while the torsion angles were allowed to refine, with the starting position based on the threefold averaged circular Fourier synthesis. For methyl group C10, an idealized disordered methyl group was assumed, with two positions rotated from each other by 60 ° and with a half-occupancy for hydrogen atoms.
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and SADABS (Sheldrick, 2001); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL.
C20H22O6 | Dx = 1.332 Mg m−3 |
Mr = 358.38 | Melting point: 445–446 K K |
Monoclinic, I2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.2304 (2) Å | Cell parameters from 8192 reflections |
b = 16.4299 (2) Å | θ = 1.7–30.6° |
c = 17.8325 (2) Å | µ = 0.10 mm−1 |
β = 93.999 (1)° | T = 183 K |
V = 3574.61 (8) Å3 | Needle, colourless |
Z = 8 | 0.60 × 0.12 × 0.10 mm |
F(000) = 1520 |
Siemens SMART CCD diffractometer | 5495 independent reflections |
Radiation source: fine-focus sealed tube | 3717 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
ω scans | θmax = 30.6°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −17→17 |
Tmin = 0.943, Tmax = 0.990 | k = −23→23 |
24968 measured reflections | l = −25→25 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0721P)2 + 1.3054P] where P = (Fo2 + 2Fc2)/3 |
5495 reflections | (Δ/σ)max = 0.001 |
340 parameters | Δρmax = 0.24 e Å−3 |
472 restraints | Δρmin = −0.28 e Å−3 |
C20H22O6 | V = 3574.61 (8) Å3 |
Mr = 358.38 | Z = 8 |
Monoclinic, I2/c | Mo Kα radiation |
a = 12.2304 (2) Å | µ = 0.10 mm−1 |
b = 16.4299 (2) Å | T = 183 K |
c = 17.8325 (2) Å | 0.60 × 0.12 × 0.10 mm |
β = 93.999 (1)° |
Siemens SMART CCD diffractometer | 5495 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 3717 reflections with I > 2σ(I) |
Tmin = 0.943, Tmax = 0.990 | Rint = 0.041 |
24968 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 472 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.24 e Å−3 |
5495 reflections | Δρmin = −0.28 e Å−3 |
340 parameters |
Experimental. Data were collected at low temperature using a Siemens SMART CCD diffractometer equiped with a LT-2 device. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal–to–detector distance of 3.97 cm, 30 s per frame. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 8192 reflections with I>10σ(I) after integration of all the frames data using SAINT (Siemens, 1995). |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.92142 (9) | 1.03869 (7) | 0.58033 (7) | 0.0323 (2) | |
C2 | 0.91740 (10) | 1.12482 (7) | 0.58918 (7) | 0.0367 (3) | |
C3 | 0.99624 (11) | 1.16817 (7) | 0.63208 (7) | 0.0399 (3) | |
C4 | 1.08127 (10) | 1.12458 (7) | 0.66849 (7) | 0.0377 (3) | |
C5 | 1.09070 (10) | 1.04049 (7) | 0.66102 (7) | 0.0353 (3) | |
H5 | 1.1503 | 1.0122 | 0.6862 | 0.043 (4)* | |
C6 | 1.01266 (9) | 0.99870 (7) | 0.61681 (7) | 0.0322 (2) | |
C7 | 0.83167 (9) | 0.99771 (7) | 0.53715 (7) | 0.0360 (3) | |
C8 | 0.82704 (9) | 0.90604 (7) | 0.52657 (7) | 0.0330 (2) | |
H8 | 0.8954 | 0.8870 | 0.5043 | 0.035 (3)* | |
C10 | 0.98710 (15) | 1.25914 (8) | 0.63964 (10) | 0.0576 (4) | |
H10A | 1.0578 | 1.2814 | 0.6591 | 0.053 (4)* | 0.50 |
H10B | 0.9311 | 1.2722 | 0.6745 | 0.053 (4)* | 0.50 |
H10C | 0.9665 | 1.2830 | 0.5903 | 0.053 (4)* | 0.50 |
H10D | 0.9124 | 1.2763 | 0.6235 | 0.053 (4)* | 0.50 |
H10E | 1.0392 | 1.2856 | 0.6081 | 0.053 (4)* | 0.50 |
H10F | 1.0038 | 1.2747 | 0.6922 | 0.053 (4)* | 0.50 |
C11 | 1.24148 (13) | 1.12768 (10) | 0.75327 (9) | 0.0541 (4) | |
H11A | 1.2098 | 1.0878 | 0.7864 | 0.056 (5)* | |
H11B | 1.2855 | 1.1670 | 0.7837 | 0.076 (6)* | |
H11C | 1.2882 | 1.0996 | 0.7190 | 0.059 (5)* | |
C12 | 1.11015 (12) | 0.87425 (8) | 0.64192 (10) | 0.0540 (4) | |
H12A | 1.1791 | 0.8960 | 0.6253 | 0.063 (5)* | |
H12B | 1.1043 | 0.8164 | 0.6290 | 0.058 (5)* | |
H12C | 1.1089 | 0.8808 | 0.6965 | 0.062 (5)* | |
C13 | 0.72712 (11) | 0.88020 (8) | 0.47592 (8) | 0.0430 (3) | |
H13A | 0.7296 | 0.8213 | 0.4675 | 0.058 (5)* | |
H13B | 0.7276 | 0.9086 | 0.4276 | 0.053 (4)* | |
H13C | 0.6601 | 0.8941 | 0.5002 | 0.062 (5)* | |
O1 | 0.83414 (8) | 1.16840 (5) | 0.55614 (6) | 0.0506 (3) | |
H1 | 0.7899 | 1.1369 | 0.5326 | 0.086 (7)* | |
O2 | 1.15567 (8) | 1.16928 (6) | 0.71075 (6) | 0.0500 (3) | |
O3 | 1.02006 (7) | 0.91742 (5) | 0.60535 (6) | 0.0416 (2) | |
O4 | 0.75449 (8) | 1.03771 (6) | 0.50730 (7) | 0.0554 (3) | |
O5 | 0.77840 (9) | 0.90076 (7) | 0.65288 (6) | 0.0554 (3) | |
C9 | 0.8184 (5) | 0.8668 (2) | 0.6026 (3) | 0.0376 (8) | 0.806 (3) |
C14 | 0.8560 (3) | 0.78139 (16) | 0.61556 (14) | 0.0328 (5) | 0.806 (3) |
C15 | 0.90368 (19) | 0.73521 (13) | 0.56148 (14) | 0.0378 (4) | 0.806 (3) |
H15 | 0.9138 | 0.7585 | 0.5137 | 0.051 (3)* | 0.806 (3) |
C16 | 0.93689 (14) | 0.65544 (11) | 0.57579 (12) | 0.0386 (4) | 0.806 (3) |
H16 | 0.9701 | 0.6248 | 0.5384 | 0.051 (3)* | 0.806 (3) |
C17 | 0.9212 (3) | 0.62125 (14) | 0.64487 (16) | 0.0364 (6) | 0.806 (3) |
C18 | 0.87338 (15) | 0.66671 (10) | 0.70002 (10) | 0.0410 (4) | 0.806 (3) |
H18 | 0.8625 | 0.6432 | 0.7476 | 0.051 (3)* | 0.806 (3) |
C19 | 0.84217 (16) | 0.74575 (11) | 0.68499 (11) | 0.0393 (4) | 0.806 (3) |
H19 | 0.8104 | 0.7767 | 0.7229 | 0.051 (3)* | 0.806 (3) |
C20 | 1.0117 (3) | 0.49795 (17) | 0.61708 (18) | 0.0544 (7) | 0.806 (3) |
H20A | 0.9726 | 0.4929 | 0.5674 | 0.062 (4)* | 0.806 (3) |
H20B | 1.0257 | 0.4436 | 0.6384 | 0.062 (4)* | 0.806 (3) |
H20C | 1.0815 | 0.5260 | 0.6122 | 0.062 (4)* | 0.806 (3) |
O6 | 0.94709 (11) | 0.54318 (7) | 0.66508 (7) | 0.0487 (4) | 0.806 (3) |
C9A | 0.8296 (18) | 0.8539 (8) | 0.6017 (9) | 0.031 (2) | 0.194 (3) |
C14A | 0.8693 (10) | 0.7689 (6) | 0.5924 (5) | 0.0260 (18) | 0.194 (3) |
C15A | 0.8998 (7) | 0.7357 (5) | 0.5258 (5) | 0.0337 (16) | 0.194 (3) |
H15A | 0.8946 | 0.7670 | 0.4809 | 0.051 (3)* | 0.194 (3) |
C16A | 0.9378 (5) | 0.6564 (4) | 0.5249 (4) | 0.0363 (15) | 0.194 (3) |
H16A | 0.9555 | 0.6318 | 0.4791 | 0.051 (3)* | 0.194 (3) |
C17A | 0.9499 (5) | 0.6126 (4) | 0.5925 (4) | 0.0327 (15) | 0.194 (3) |
C18A | 0.9202 (12) | 0.6454 (6) | 0.6605 (6) | 0.037 (2) | 0.194 (3) |
H18A | 0.9269 | 0.6147 | 0.7057 | 0.051 (3)* | 0.194 (3) |
C19A | 0.8804 (6) | 0.7251 (4) | 0.6593 (4) | 0.0375 (15) | 0.194 (3) |
H19A | 0.8606 | 0.7497 | 0.7046 | 0.051 (3)* | 0.194 (3) |
C20A | 1.0201 (15) | 0.4895 (8) | 0.6501 (7) | 0.068 (4) | 0.194 (3) |
H20D | 1.0625 | 0.5235 | 0.6867 | 0.062 (4)* | 0.194 (3) |
H20E | 1.0641 | 0.4424 | 0.6372 | 0.062 (4)* | 0.194 (3) |
H20F | 0.9531 | 0.4708 | 0.6718 | 0.062 (4)* | 0.194 (3) |
O6A | 0.9917 (4) | 0.5363 (3) | 0.5833 (3) | 0.0475 (15) | 0.194 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0288 (5) | 0.0261 (5) | 0.0411 (6) | 0.0020 (4) | −0.0048 (5) | −0.0004 (4) |
C2 | 0.0374 (6) | 0.0286 (5) | 0.0428 (7) | 0.0056 (5) | −0.0063 (5) | −0.0012 (5) |
C3 | 0.0464 (7) | 0.0279 (5) | 0.0441 (7) | 0.0005 (5) | −0.0054 (6) | −0.0041 (5) |
C4 | 0.0373 (6) | 0.0356 (6) | 0.0390 (6) | −0.0066 (5) | −0.0045 (5) | −0.0022 (5) |
C5 | 0.0294 (5) | 0.0332 (6) | 0.0420 (6) | −0.0020 (4) | −0.0063 (5) | 0.0043 (5) |
C6 | 0.0282 (5) | 0.0262 (5) | 0.0416 (6) | 0.0000 (4) | −0.0027 (5) | 0.0037 (5) |
C7 | 0.0285 (5) | 0.0312 (5) | 0.0470 (7) | 0.0036 (4) | −0.0065 (5) | −0.0010 (5) |
C8 | 0.0252 (5) | 0.0289 (5) | 0.0443 (6) | −0.0007 (4) | −0.0013 (5) | −0.0033 (5) |
C10 | 0.0738 (11) | 0.0310 (6) | 0.0652 (10) | 0.0027 (6) | −0.0156 (8) | −0.0101 (6) |
C11 | 0.0460 (8) | 0.0586 (9) | 0.0547 (9) | −0.0098 (7) | −0.0179 (7) | −0.0046 (7) |
C12 | 0.0397 (7) | 0.0337 (6) | 0.0849 (12) | 0.0070 (5) | −0.0220 (7) | 0.0097 (7) |
C13 | 0.0327 (6) | 0.0424 (7) | 0.0529 (8) | −0.0056 (5) | −0.0055 (6) | −0.0063 (6) |
O1 | 0.0509 (6) | 0.0295 (4) | 0.0678 (7) | 0.0124 (4) | −0.0211 (5) | −0.0053 (4) |
O2 | 0.0506 (6) | 0.0415 (5) | 0.0549 (6) | −0.0081 (4) | −0.0173 (5) | −0.0073 (4) |
O3 | 0.0310 (4) | 0.0251 (4) | 0.0663 (6) | 0.0027 (3) | −0.0139 (4) | 0.0039 (4) |
O4 | 0.0429 (5) | 0.0373 (5) | 0.0816 (7) | 0.0093 (4) | −0.0281 (5) | −0.0045 (5) |
O5 | 0.0574 (6) | 0.0579 (6) | 0.0521 (6) | −0.0026 (5) | 0.0134 (5) | −0.0057 (5) |
C9 | 0.0279 (17) | 0.0278 (9) | 0.0561 (16) | −0.0016 (8) | −0.0048 (11) | −0.0031 (9) |
C14 | 0.0285 (11) | 0.0293 (9) | 0.0404 (14) | −0.0044 (7) | 0.0006 (10) | −0.0056 (9) |
C15 | 0.0400 (10) | 0.0338 (9) | 0.0407 (11) | −0.0010 (7) | 0.0103 (11) | 0.0015 (10) |
C16 | 0.0384 (8) | 0.0331 (9) | 0.0448 (11) | 0.0006 (7) | 0.0059 (7) | −0.0007 (8) |
C17 | 0.0317 (9) | 0.0343 (12) | 0.0419 (15) | −0.0048 (9) | −0.0056 (9) | 0.0000 (9) |
C18 | 0.0460 (9) | 0.0423 (9) | 0.0338 (8) | −0.0056 (7) | −0.0039 (7) | −0.0001 (7) |
C19 | 0.0425 (10) | 0.0383 (9) | 0.0365 (9) | −0.0048 (7) | −0.0005 (7) | −0.0086 (7) |
C20 | 0.0545 (14) | 0.0325 (11) | 0.076 (2) | 0.0017 (10) | 0.0053 (15) | −0.0001 (14) |
O6 | 0.0561 (8) | 0.0361 (6) | 0.0532 (7) | 0.0034 (5) | −0.0006 (6) | 0.0076 (5) |
C9A | 0.019 (4) | 0.050 (5) | 0.026 (4) | −0.001 (5) | 0.014 (3) | 0.005 (4) |
C14A | 0.023 (4) | 0.026 (4) | 0.030 (5) | −0.004 (3) | 0.007 (4) | 0.002 (3) |
C15A | 0.032 (3) | 0.028 (3) | 0.042 (4) | 0.003 (2) | 0.008 (4) | −0.002 (3) |
C16A | 0.039 (3) | 0.031 (3) | 0.039 (4) | 0.004 (2) | 0.001 (3) | 0.000 (3) |
C17A | 0.034 (3) | 0.027 (3) | 0.036 (4) | −0.008 (2) | −0.007 (3) | 0.004 (3) |
C18A | 0.044 (4) | 0.036 (5) | 0.030 (4) | −0.004 (4) | −0.008 (4) | 0.005 (3) |
C19A | 0.041 (4) | 0.038 (3) | 0.033 (3) | −0.008 (3) | 0.003 (3) | −0.003 (3) |
C20A | 0.103 (9) | 0.032 (5) | 0.066 (8) | 0.006 (5) | −0.017 (7) | −0.002 (5) |
O6A | 0.052 (3) | 0.027 (2) | 0.062 (3) | 0.004 (2) | −0.014 (2) | 0.003 (2) |
C1—C6 | 1.4137 (15) | O1—H1 | 0.840 |
C1—C2 | 1.4252 (16) | O5—C9A | 1.377 (14) |
C1—C7 | 1.4605 (16) | O5—C9 | 1.189 (4) |
C2—O1 | 1.3464 (14) | C9—C14 | 1.490 (3) |
C2—C3 | 1.3854 (17) | C14—C19 | 1.391 (3) |
C3—C4 | 1.3863 (18) | C14—C15 | 1.387 (3) |
C3—C10 | 1.5057 (18) | C15—C16 | 1.390 (3) |
C4—O2 | 1.3564 (14) | C15—H15 | 0.950 |
C4—C5 | 1.3936 (17) | C16—C17 | 1.379 (4) |
C5—C6 | 1.3780 (16) | C16—H16 | 0.950 |
C5—H5 | 0.950 | C17—O6 | 1.364 (3) |
C6—O3 | 1.3550 (14) | C17—C18 | 1.395 (3) |
C7—O4 | 1.2394 (14) | C18—C19 | 1.375 (3) |
C7—C8 | 1.5184 (16) | C18—H18 | 0.950 |
C8—C9A | 1.589 (14) | C19—H19 | 0.950 |
C8—C9 | 1.512 (5) | C20—O6 | 1.415 (3) |
C8—C13 | 1.5282 (16) | C20—H20A | 0.980 |
C8—H8 | 1.000 | C20—H20B | 0.980 |
C10—H10A | 0.980 | C20—H20C | 0.980 |
C10—H10B | 0.980 | C9A—C14A | 1.492 (12) |
C10—H10C | 0.980 | C14A—C19A | 1.391 (10) |
C10—H10D | 0.980 | C14A—C15A | 1.382 (9) |
C10—H10E | 0.980 | C15A—C16A | 1.384 (9) |
C10—H10F | 0.980 | C15A—H15A | 0.950 |
C11—O2 | 1.4257 (18) | C16A—C17A | 1.402 (9) |
C11—H11A | 0.980 | C16A—H16A | 0.950 |
C11—H11B | 0.980 | C17A—C18A | 1.398 (11) |
C11—H11C | 0.980 | C17A—O6A | 1.368 (8) |
C12—O3 | 1.4291 (14) | C18A—C19A | 1.397 (11) |
C12—H12A | 0.980 | C18A—H18A | 0.950 |
C12—H12B | 0.980 | C19A—H19A | 0.950 |
C12—H12C | 0.980 | C20A—O6A | 1.439 (10) |
C13—H13A | 0.980 | C20A—H20D | 0.980 |
C13—H13B | 0.980 | C20A—H20E | 0.980 |
C13—H13C | 0.980 | C20A—H20F | 0.980 |
C6—C1—C2 | 116.27 (10) | C8—C13—H13C | 109.5 |
C6—C1—C7 | 124.64 (10) | H13A—C13—H13C | 109.5 |
C2—C1—C7 | 119.06 (10) | H13B—C13—H13C | 109.5 |
O1—C2—C3 | 116.38 (11) | C2—O1—H1 | 109.5 |
O1—C2—C1 | 120.69 (11) | C4—O2—C11 | 118.44 (11) |
C3—C2—C1 | 122.93 (11) | C6—O3—C12 | 118.55 (10) |
C2—C3—C4 | 117.62 (11) | O5—C9—C14 | 117.6 (4) |
C2—C3—C10 | 120.44 (12) | O5—C9—C8 | 122.3 (3) |
C4—C3—C10 | 121.93 (12) | C14—C9—C8 | 120.0 (3) |
O2—C4—C5 | 122.22 (11) | C19—C14—C15 | 118.1 (2) |
O2—C4—C3 | 115.65 (11) | C19—C14—C9 | 118.6 (2) |
C5—C4—C3 | 122.12 (11) | C15—C14—C9 | 123.2 (3) |
C6—C5—C4 | 119.34 (11) | C14—C15—C16 | 121.3 (2) |
C6—C5—H5 | 120.3 | C14—C15—H15 | 119.3 |
C4—C5—H5 | 120.3 | C16—C15—H15 | 119.3 |
O3—C6—C5 | 121.76 (10) | C17—C16—C15 | 119.38 (19) |
O3—C6—C1 | 116.58 (10) | C17—C16—H16 | 120.3 |
C5—C6—C1 | 121.66 (10) | C15—C16—H16 | 120.3 |
O4—C7—C1 | 120.25 (11) | O6—C17—C16 | 125.1 (2) |
O4—C7—C8 | 116.87 (10) | O6—C17—C18 | 114.7 (2) |
C1—C7—C8 | 122.88 (10) | C16—C17—C18 | 120.2 (2) |
C9A—C8—C7 | 115.6 (6) | C17—C18—C19 | 119.51 (19) |
C9—C8—C7 | 108.39 (17) | C17—C18—H18 | 120.2 |
C9A—C8—C13 | 108.4 (9) | C19—C18—H18 | 120.2 |
C9—C8—C13 | 108.0 (2) | C14—C19—C18 | 121.47 (19) |
C7—C8—C13 | 111.74 (10) | C14—C19—H19 | 119.3 |
C9A—C8—H8 | 101.4 | C18—C19—H19 | 119.3 |
C9—C8—H8 | 109.6 | C17—O6—C20 | 117.6 (2) |
C7—C8—H8 | 109.6 | O5—C9A—C8 | 105.9 (8) |
C13—C8—H8 | 109.6 | O5—C9A—C14A | 139.8 (11) |
C3—C10—H10A | 109.5 | C8—C9A—C14A | 113.5 (10) |
C3—C10—H10B | 109.5 | C19A—C14A—C15A | 121.2 (8) |
H10A—C10—H10B | 109.5 | C19A—C14A—C9A | 113.7 (9) |
C3—C10—H10C | 109.5 | C15A—C14A—C9A | 125.1 (9) |
H10A—C10—H10C | 109.5 | C14A—C15A—C16A | 119.5 (8) |
H10B—C10—H10C | 109.5 | C14A—C15A—H15A | 120.3 |
C3—C10—H10D | 109.5 | C16A—C15A—H15A | 120.3 |
C3—C10—H10E | 109.5 | C17A—C16A—C15A | 119.3 (7) |
H10D—C10—H10E | 109.5 | C17A—C16A—H16A | 120.4 |
C3—C10—H10F | 109.5 | C15A—C16A—H16A | 120.4 |
H10D—C10—H10F | 109.5 | C18A—C17A—C16A | 122.0 (7) |
H10E—C10—H10F | 109.5 | C18A—C17A—O6A | 125.4 (7) |
O2—C11—H11A | 109.5 | C16A—C17A—O6A | 112.7 (6) |
O2—C11—H11B | 109.5 | C17A—C18A—C19A | 117.4 (9) |
H11A—C11—H11B | 109.5 | C17A—C18A—H18A | 121.3 |
O2—C11—H11C | 109.5 | C19A—C18A—H18A | 121.3 |
H11A—C11—H11C | 109.5 | C14A—C19A—C18A | 120.7 (8) |
H11B—C11—H11C | 109.5 | C14A—C19A—H19A | 119.7 |
O3—C12—H12A | 109.5 | C18A—C19A—H19A | 119.7 |
O3—C12—H12B | 109.5 | O6A—C20A—H20D | 109.5 |
H12A—C12—H12B | 109.5 | O6A—C20A—H20E | 109.5 |
O3—C12—H12C | 109.5 | H20D—C20A—H20E | 109.5 |
H12A—C12—H12C | 109.5 | O6A—C20A—H20F | 109.5 |
H12B—C12—H12C | 109.5 | H20D—C20A—H20F | 109.5 |
C8—C13—H13A | 109.5 | H20E—C20A—H20F | 109.5 |
C8—C13—H13B | 109.5 | C17A—O6A—C20A | 117.5 (8) |
H13A—C13—H13B | 109.5 | ||
C6—C1—C2—O1 | 179.52 (12) | C7—C8—C9—C14 | −155.7 (4) |
C7—C1—C2—O1 | −2.29 (19) | C13—C8—C9—C14 | 83.1 (4) |
C6—C1—C2—C3 | −1.29 (19) | O5—C9—C14—C19 | 0.2 (6) |
C7—C1—C2—C3 | 176.89 (13) | C8—C9—C14—C19 | −177.0 (3) |
O1—C2—C3—C4 | 178.22 (13) | O5—C9—C14—C15 | 179.8 (4) |
C1—C2—C3—C4 | −1.0 (2) | C8—C9—C14—C15 | 2.6 (6) |
O1—C2—C3—C10 | −0.4 (2) | C19—C14—C15—C16 | 0.0 (4) |
C1—C2—C3—C10 | −179.65 (14) | C9—C14—C15—C16 | −179.5 (3) |
C2—C3—C4—O2 | −179.05 (12) | C14—C15—C16—C17 | 0.6 (4) |
C10—C3—C4—O2 | −0.4 (2) | C15—C16—C17—O6 | 178.0 (2) |
C2—C3—C4—C5 | 2.1 (2) | C15—C16—C17—C18 | −0.7 (4) |
C10—C3—C4—C5 | −179.30 (14) | O6—C17—C18—C19 | −178.81 (18) |
O2—C4—C5—C6 | −179.56 (12) | C16—C17—C18—C19 | 0.0 (3) |
C3—C4—C5—C6 | −0.8 (2) | C15—C14—C19—C18 | −0.7 (4) |
C4—C5—C6—O3 | 177.49 (12) | C9—C14—C19—C18 | 178.9 (3) |
C4—C5—C6—C1 | −1.73 (19) | C17—C18—C19—C14 | 0.7 (3) |
C2—C1—C6—O3 | −176.58 (11) | C16—C17—O6—C20 | 11.4 (4) |
C7—C1—C6—O3 | 5.35 (18) | C18—C17—O6—C20 | −169.9 (2) |
C2—C1—C6—C5 | 2.67 (18) | C7—C8—C9A—O5 | 31.4 (16) |
C7—C1—C6—C5 | −175.40 (12) | C13—C8—C9A—O5 | −94.9 (12) |
C6—C1—C7—O4 | 179.63 (13) | C7—C8—C9A—C14A | −156.9 (11) |
C2—C1—C7—O4 | 1.6 (2) | C13—C8—C9A—C14A | 76.8 (15) |
C6—C1—C7—C8 | −0.1 (2) | O5—C9A—C14A—C19A | −17 (3) |
C2—C1—C7—C8 | −178.16 (12) | C8—C9A—C14A—C19A | 174.9 (11) |
O4—C7—C8—C9A | −121.7 (9) | O5—C9A—C14A—C15A | 166 (2) |
C1—C7—C8—C9A | 58.1 (9) | C8—C9A—C14A—C15A | −1 (2) |
O4—C7—C8—C9 | −115.9 (3) | C19A—C14A—C15A—C16A | 2.7 (15) |
C1—C7—C8—C9 | 63.9 (3) | C9A—C14A—C15A—C16A | 178.5 (14) |
O4—C7—C8—C13 | 2.97 (17) | C14A—C15A—C16A—C17A | −3.2 (12) |
C1—C7—C8—C13 | −177.25 (12) | C15A—C16A—C17A—C18A | 2.8 (12) |
C5—C4—O2—C11 | −4.8 (2) | C15A—C16A—C17A—O6A | −177.9 (6) |
C3—C4—O2—C11 | 176.27 (13) | C16A—C17A—C18A—C19A | −1.7 (15) |
C5—C6—O3—C12 | 1.58 (19) | O6A—C17A—C18A—C19A | 179.0 (8) |
C1—C6—O3—C12 | −179.17 (13) | C15A—C14A—C19A—C18A | −1.6 (16) |
C9A—O5—C9—C14 | 14 (9) | C9A—C14A—C19A—C18A | −177.9 (13) |
C9A—O5—C9—C8 | −169 (10) | C17A—C18A—C19A—C14A | 1.1 (16) |
C7—C8—C9—O5 | 27.2 (6) | C18A—C17A—O6A—C20A | −8.0 (14) |
C13—C8—C9—O5 | −94.0 (5) | C16A—C17A—O6A—C20A | 172.6 (10) |
Experimental details
Crystal data | |
Chemical formula | C20H22O6 |
Mr | 358.38 |
Crystal system, space group | Monoclinic, I2/c |
Temperature (K) | 183 |
a, b, c (Å) | 12.2304 (2), 16.4299 (2), 17.8325 (2) |
β (°) | 93.999 (1) |
V (Å3) | 3574.61 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.60 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Siemens SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.943, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24968, 5495, 3717 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.716 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.144, 0.99 |
No. of reflections | 5495 |
No. of parameters | 340 |
No. of restraints | 472 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.28 |
Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SAINT and SADABS (Sheldrick, 2001), SHELXTL (Bruker, 1997), SHELXTL, DIAMOND (Brandenburg, 2000).
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In an investigation of the selective inhibition of certain rat heart enzymes caused by a series of lipophilic flavones, the inhibition effect of eight flavones, which are derivatives of either O-methylluteolin or O-methylapigenin, was studied (Gaillard et al., 1996). The crystal structure of one of the O-methylluteolin derivatives, 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3,8-dimethyl-4H-1-benzopyran-4-one, has recently been determined by Stomberg et al. (2002). A second one of these flavones, the O-methylapigenin derivative 2-(4-methoxyphenyl)-5,7-dimethoxy-3,8-dimethyl-4H-1-benzopyran-4-one, was prepared by acid-catalyzed cyclization and dehydration of 1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-3-(4-methoxyphenyl)-2-methyl-1,3- propanedione, (I). This paper describes the crystal structure of this synthetic intermediate, (I).
A perspective view of (I), together with the atom-numbering scheme, is shown in Fig. 1. The disorder in the methoxyphenyl group is shown in Fig. 2, and the packing of the molecules in Fig. 3. The molecules are held together by van der Waals forces. There is an intramolecular hydrogen bond between the hydroxy hydrogen atom H(O1) and the oxygen atom O4 in the neighbouring carbonyl group. The benzylic carbon atom C7, the hydroxy oxygen atom O1, and the methyl carbon atom C10 are twisted out of the C1/C2/C3/C4/C5/C6 ring plane by −0.094 (2), −0.014 (2) and 0.018 (3) Å, respectively. The methyl carbon atoms in the methoxy groups are situated close to the respective benzene ring planes [torsion angles: C5–C4–O2–C11 − 4.8 (2)°, C5–C6–O3–C12 1.6 (2)°, C16–C17–O6–C20 11.4 (4)° and C16A–C17A–O6A–C20A 172.6 (10)°].