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The title compound, C
19H
18O
8 [systematic name: 5-hydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-3,7-dimethoxychromen-4-one], an extract from
Premna tomentosa willd, is used in the Siddha system of medicine practiced in South India. The dihedral angle between the mean planes through the benzopyran moiety and benzene ring is 38.60 (7)°. A strong O—H
O intramolecular hydrogen bond is observed in the molecular structure. O—H
O and C—H
O hydrogen bonds and π–π interactions stabilize the molecules in the crystal packing.
Supporting information
CCDC reference: 270262
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.052
- wR factor = 0.160
- Data-to-parameter ratio = 20.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 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
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
5-hydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-3,7-dimethoxychromen-4-one
top
Crystal data top
C19H18O8 | F(000) = 1568 |
Mr = 374.33 | Dx = 1.422 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5092 reflections |
a = 30.958 (7) Å | θ = 1.3–30.0° |
b = 7.9544 (19) Å | µ = 0.11 mm−1 |
c = 14.263 (6) Å | T = 293 K |
β = 95.53 (3)° | Block, yellow |
V = 3495.9 (18) Å3 | 0.25 × 0.22 × 0.20 mm |
Z = 8 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.061 |
Radiation source: fine-focus sealed tube | θmax = 30.0°, θmin = 1.3° |
Graphite monochromator | h = −43→43 |
non–profiled w/2θ scans | k = −11→11 |
10241 measured reflections | l = −20→0 |
5092 independent reflections | 3 standard reflections every 200 reflections |
2382 reflections with I > 2σ(I) | intensity decay: 1% |
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)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.160 | w = 1/[σ2(Fo2) + (0.0772P)2 + 0.2525P] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
5092 reflections | Δρmax = 0.24 e Å−3 |
245 parameters | Δρmin = −0.22 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: 0.0018 (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 | 0.04782 (4) | 0.07116 (17) | 0.66077 (10) | 0.0369 (4) | |
C10 | −0.01255 (6) | −0.1082 (3) | 0.61098 (14) | 0.0331 (4) | |
C8 | −0.01906 (6) | 0.1971 (3) | 0.61443 (16) | 0.0386 (5) | |
H8 | −0.0066 | 0.3020 | 0.6272 | 0.046* | |
C6 | −0.08124 (6) | 0.0255 (3) | 0.56013 (15) | 0.0404 (5) | |
H6 | −0.1103 | 0.0178 | 0.5371 | 0.048* | |
C13 | 0.11919 (6) | −0.0155 (3) | 0.70542 (15) | 0.0353 (5) | |
O5 | 0.08850 (5) | −0.3535 (2) | 0.66722 (12) | 0.0529 (5) | |
O2 | 0.00002 (5) | −0.39961 (19) | 0.60759 (13) | 0.0596 (5) | |
C3 | 0.05931 (6) | −0.2241 (3) | 0.66084 (15) | 0.0365 (5) | |
C7 | −0.06244 (6) | 0.1817 (3) | 0.58052 (16) | 0.0385 (5) | |
O6 | 0.21434 (5) | −0.1405 (2) | 0.86689 (12) | 0.0520 (4) | |
C2 | 0.07390 (6) | −0.0663 (3) | 0.67636 (15) | 0.0336 (4) | |
O7 | 0.24661 (5) | 0.1293 (2) | 0.78183 (12) | 0.0591 (5) | |
C9 | 0.00481 (6) | 0.0519 (3) | 0.62853 (14) | 0.0334 (4) | |
C4 | 0.01438 (7) | −0.2557 (3) | 0.62534 (16) | 0.0397 (5) | |
O8 | 0.19377 (5) | 0.3136 (2) | 0.65109 (13) | 0.0664 (6) | |
H8A | 0.2189 | 0.3309 | 0.6723 | 0.100* | |
O3 | −0.07532 (5) | −0.2678 (2) | 0.55236 (13) | 0.0571 (5) | |
H3 | −0.0576 | −0.3434 | 0.5639 | 0.086* | |
O4 | −0.08420 (5) | 0.3292 (2) | 0.56782 (13) | 0.0548 (5) | |
C17 | 0.17845 (7) | 0.1749 (3) | 0.69296 (16) | 0.0424 (5) | |
C5 | −0.05640 (6) | −0.1182 (3) | 0.57431 (15) | 0.0388 (5) | |
C14 | 0.14476 (6) | −0.1086 (3) | 0.77352 (15) | 0.0397 (5) | |
H14 | 0.1334 | −0.2035 | 0.8002 | 0.048* | |
C15 | 0.18680 (6) | −0.0590 (3) | 0.80067 (15) | 0.0403 (5) | |
C16 | 0.20362 (6) | 0.0826 (3) | 0.76069 (16) | 0.0412 (5) | |
C18 | 0.13585 (6) | 0.1261 (3) | 0.66601 (16) | 0.0405 (5) | |
H18 | 0.1187 | 0.1887 | 0.6217 | 0.049* | |
C12 | −0.12893 (8) | 0.3247 (4) | 0.5335 (2) | 0.0677 (8) | |
H12A | −0.1400 | 0.4374 | 0.5278 | 0.101* | |
H12B | −0.1448 | 0.2626 | 0.5766 | 0.101* | |
H12C | −0.1321 | 0.2712 | 0.4729 | 0.101* | |
C19 | 0.19887 (9) | −0.2936 (4) | 0.9049 (2) | 0.0730 (9) | |
H19A | 0.2207 | −0.3386 | 0.9504 | 0.110* | |
H19B | 0.1926 | −0.3736 | 0.8550 | 0.110* | |
H19C | 0.1729 | −0.2713 | 0.9346 | 0.110* | |
C20 | 0.25658 (9) | 0.2081 (4) | 0.8710 (2) | 0.0792 (10) | |
H20A | 0.2870 | 0.2348 | 0.8794 | 0.119* | |
H20B | 0.2496 | 0.1332 | 0.9201 | 0.119* | |
H20C | 0.2399 | 0.3094 | 0.8736 | 0.119* | |
C11 | 0.08058 (10) | −0.4899 (4) | 0.7266 (2) | 0.0772 (9) | |
H11A | 0.1034 | −0.5714 | 0.7249 | 0.116* | |
H11B | 0.0533 | −0.5409 | 0.7053 | 0.116* | |
H11C | 0.0797 | −0.4502 | 0.7899 | 0.116* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0286 (7) | 0.0307 (7) | 0.0504 (9) | −0.0023 (5) | −0.0019 (6) | −0.0023 (6) |
C10 | 0.0293 (9) | 0.0320 (10) | 0.0373 (12) | −0.0055 (8) | −0.0005 (8) | 0.0006 (9) |
C8 | 0.0335 (10) | 0.0307 (11) | 0.0508 (14) | −0.0019 (8) | −0.0003 (9) | −0.0057 (10) |
C6 | 0.0282 (9) | 0.0469 (13) | 0.0453 (13) | −0.0041 (9) | 0.0002 (9) | 0.0020 (10) |
C13 | 0.0264 (9) | 0.0378 (11) | 0.0416 (12) | −0.0002 (8) | 0.0019 (8) | −0.0042 (10) |
O5 | 0.0453 (9) | 0.0395 (9) | 0.0724 (12) | 0.0071 (7) | −0.0015 (8) | 0.0003 (8) |
O2 | 0.0541 (10) | 0.0317 (8) | 0.0888 (14) | −0.0103 (8) | −0.0151 (9) | 0.0016 (8) |
C3 | 0.0349 (10) | 0.0318 (10) | 0.0418 (13) | 0.0017 (8) | −0.0010 (9) | 0.0002 (9) |
C7 | 0.0330 (10) | 0.0395 (12) | 0.0428 (13) | 0.0027 (8) | 0.0026 (9) | −0.0030 (10) |
O6 | 0.0366 (8) | 0.0562 (10) | 0.0608 (11) | 0.0034 (7) | −0.0077 (7) | 0.0134 (9) |
C2 | 0.0279 (9) | 0.0343 (11) | 0.0378 (12) | −0.0003 (8) | −0.0002 (8) | 0.0008 (9) |
O7 | 0.0311 (8) | 0.0811 (13) | 0.0631 (12) | −0.0111 (8) | −0.0048 (7) | 0.0073 (10) |
C9 | 0.0278 (9) | 0.0364 (11) | 0.0360 (12) | −0.0034 (8) | 0.0023 (8) | −0.0008 (9) |
C4 | 0.0397 (11) | 0.0333 (11) | 0.0450 (14) | −0.0066 (9) | −0.0011 (10) | 0.0016 (10) |
O8 | 0.0422 (9) | 0.0700 (12) | 0.0832 (14) | −0.0226 (9) | −0.0131 (9) | 0.0253 (10) |
O3 | 0.0431 (9) | 0.0374 (9) | 0.0864 (13) | −0.0127 (7) | −0.0161 (8) | 0.0044 (9) |
O4 | 0.0377 (8) | 0.0449 (10) | 0.0792 (13) | 0.0123 (7) | −0.0084 (8) | −0.0074 (8) |
C17 | 0.0327 (10) | 0.0439 (13) | 0.0502 (14) | −0.0072 (9) | 0.0019 (9) | 0.0024 (10) |
C5 | 0.0341 (10) | 0.0383 (11) | 0.0432 (13) | −0.0093 (9) | −0.0006 (9) | 0.0018 (10) |
C14 | 0.0338 (10) | 0.0385 (11) | 0.0466 (13) | −0.0017 (9) | 0.0027 (9) | 0.0009 (10) |
C15 | 0.0322 (10) | 0.0472 (13) | 0.0411 (13) | 0.0074 (9) | 0.0017 (9) | −0.0005 (10) |
C16 | 0.0271 (9) | 0.0493 (13) | 0.0465 (13) | −0.0003 (9) | 0.0001 (9) | −0.0025 (11) |
C18 | 0.0319 (10) | 0.0393 (12) | 0.0490 (14) | −0.0008 (9) | −0.0024 (9) | 0.0011 (10) |
C12 | 0.0337 (12) | 0.0688 (18) | 0.099 (2) | 0.0152 (12) | −0.0037 (13) | −0.0063 (16) |
C19 | 0.0580 (16) | 0.075 (2) | 0.083 (2) | −0.0011 (15) | −0.0082 (15) | 0.0364 (17) |
C20 | 0.0680 (19) | 0.088 (2) | 0.076 (2) | −0.0259 (17) | −0.0197 (16) | −0.0058 (18) |
C11 | 0.079 (2) | 0.0453 (16) | 0.104 (2) | 0.0076 (15) | −0.0074 (18) | 0.0250 (16) |
Geometric parameters (Å, º) top
O1—C2 | 1.365 (2) | O8—C17 | 1.361 (3) |
O1—C9 | 1.375 (2) | O8—H8A | 0.82 |
C10—C9 | 1.395 (3) | O3—C5 | 1.350 (2) |
C10—C5 | 1.409 (3) | O3—H3 | 0.82 |
C10—C4 | 1.443 (3) | O4—C12 | 1.424 (3) |
C8—C9 | 1.376 (3) | C17—C16 | 1.391 (3) |
C8—C7 | 1.388 (3) | C17—C18 | 1.393 (3) |
C8—H8 | 0.93 | C14—C15 | 1.379 (3) |
C6—C5 | 1.381 (3) | C14—H14 | 0.93 |
C6—C7 | 1.391 (3) | C15—C16 | 1.387 (3) |
C6—H6 | 0.93 | C18—H18 | 0.93 |
C13—C18 | 1.381 (3) | C12—H12A | 0.96 |
C13—C14 | 1.404 (3) | C12—H12B | 0.96 |
C13—C2 | 1.480 (3) | C12—H12C | 0.96 |
O5—C3 | 1.367 (2) | C19—H19A | 0.96 |
O5—C11 | 1.412 (3) | C19—H19B | 0.96 |
O2—C4 | 1.245 (2) | C19—H19C | 0.96 |
C3—C2 | 1.345 (3) | C20—H20A | 0.96 |
C3—C4 | 1.455 (3) | C20—H20B | 0.96 |
C7—O4 | 1.356 (2) | C20—H20C | 0.96 |
O6—C15 | 1.373 (2) | C11—H11A | 0.96 |
O6—C19 | 1.434 (3) | C11—H11B | 0.96 |
O7—C16 | 1.387 (2) | C11—H11C | 0.96 |
O7—C20 | 1.425 (3) | | |
| | | |
C2—O1—C9 | 120.28 (15) | O3—C5—C10 | 121.12 (19) |
C9—C10—C5 | 117.32 (18) | C6—C5—C10 | 120.68 (19) |
C9—C10—C4 | 120.63 (17) | C15—C14—C13 | 119.8 (2) |
C5—C10—C4 | 121.97 (18) | C15—C14—H14 | 120.1 |
C9—C8—C7 | 117.71 (19) | C13—C14—H14 | 120.1 |
C9—C8—H8 | 121.1 | O6—C15—C14 | 124.4 (2) |
C7—C8—H8 | 121.1 | O6—C15—C16 | 115.70 (19) |
C5—C6—C7 | 119.51 (18) | C14—C15—C16 | 119.9 (2) |
C5—C6—H6 | 120.2 | O7—C16—C15 | 121.2 (2) |
C7—C6—H6 | 120.2 | O7—C16—C17 | 118.1 (2) |
C18—C13—C14 | 120.30 (18) | C15—C16—C17 | 120.47 (19) |
C18—C13—C2 | 119.33 (18) | C13—C18—C17 | 119.7 (2) |
C14—C13—C2 | 120.36 (19) | C13—C18—H18 | 120.1 |
C3—O5—C11 | 117.81 (19) | C17—C18—H18 | 120.1 |
C2—C3—O5 | 118.83 (18) | O4—C12—H12A | 109.5 |
C2—C3—C4 | 120.86 (18) | O4—C12—H12B | 109.5 |
O5—C3—C4 | 119.78 (18) | H12A—C12—H12B | 109.5 |
O4—C7—C8 | 114.94 (19) | O4—C12—H12C | 109.5 |
O4—C7—C6 | 123.53 (19) | H12A—C12—H12C | 109.5 |
C8—C7—C6 | 121.5 (2) | H12B—C12—H12C | 109.5 |
C15—O6—C19 | 116.94 (18) | O6—C19—H19A | 109.5 |
C3—C2—O1 | 122.46 (17) | O6—C19—H19B | 109.5 |
C3—C2—C13 | 126.53 (19) | H19A—C19—H19B | 109.5 |
O1—C2—C13 | 110.89 (17) | O6—C19—H19C | 109.5 |
C16—O7—C20 | 115.63 (19) | H19A—C19—H19C | 109.5 |
O1—C9—C8 | 116.42 (17) | H19B—C19—H19C | 109.5 |
O1—C9—C10 | 120.37 (17) | O7—C20—H20A | 109.5 |
C8—C9—C10 | 123.21 (18) | O7—C20—H20B | 109.5 |
O2—C4—C10 | 121.92 (19) | H20A—C20—H20B | 109.5 |
O2—C4—C3 | 122.69 (19) | O7—C20—H20C | 109.5 |
C10—C4—C3 | 115.39 (18) | H20A—C20—H20C | 109.5 |
C17—O8—H8A | 109.5 | H20B—C20—H20C | 109.5 |
C5—O3—H3 | 109.5 | O5—C11—H11A | 109.5 |
C7—O4—C12 | 118.60 (19) | O5—C11—H11B | 109.5 |
O8—C17—C16 | 122.47 (19) | H11A—C11—H11B | 109.5 |
O8—C17—C18 | 117.7 (2) | O5—C11—H11C | 109.5 |
C16—C17—C18 | 119.8 (2) | H11A—C11—H11C | 109.5 |
O3—C5—C6 | 118.20 (18) | H11B—C11—H11C | 109.5 |
| | | |
C11—O5—C3—C2 | 127.2 (2) | C2—C3—C4—C10 | −1.5 (3) |
C11—O5—C3—C4 | −61.1 (3) | O5—C3—C4—C10 | −173.0 (2) |
C9—C8—C7—O4 | −179.80 (19) | C8—C7—O4—C12 | −179.8 (2) |
C9—C8—C7—C6 | −0.8 (3) | C6—C7—O4—C12 | 1.2 (3) |
C5—C6—C7—O4 | 179.3 (2) | C7—C6—C5—O3 | −178.9 (2) |
C5—C6—C7—C8 | 0.4 (3) | C7—C6—C5—C10 | 1.3 (3) |
O5—C3—C2—O1 | 172.20 (19) | C9—C10—C5—O3 | 177.75 (19) |
C4—C3—C2—O1 | 0.6 (3) | C4—C10—C5—O3 | 1.1 (3) |
O5—C3—C2—C13 | −3.6 (3) | C9—C10—C5—C6 | −2.4 (3) |
C4—C3—C2—C13 | −175.2 (2) | C4—C10—C5—C6 | −179.1 (2) |
C9—O1—C2—C3 | 0.4 (3) | C18—C13—C14—C15 | −0.4 (3) |
C9—O1—C2—C13 | 176.73 (16) | C2—C13—C14—C15 | −179.38 (19) |
C18—C13—C2—C3 | 139.8 (2) | C19—O6—C15—C14 | 4.5 (3) |
C14—C13—C2—C3 | −41.2 (3) | C19—O6—C15—C16 | −175.9 (2) |
C18—C13—C2—O1 | −36.3 (3) | C13—C14—C15—O6 | 179.6 (2) |
C14—C13—C2—O1 | 142.6 (2) | C13—C14—C15—C16 | 0.0 (3) |
C2—O1—C9—C8 | −179.78 (19) | C20—O7—C16—C15 | −76.8 (3) |
C2—O1—C9—C10 | −0.3 (3) | C20—O7—C16—C17 | 107.8 (3) |
C7—C8—C9—O1 | 179.04 (18) | O6—C15—C16—O7 | 4.8 (3) |
C7—C8—C9—C10 | −0.4 (3) | C14—C15—C16—O7 | −175.6 (2) |
C5—C10—C9—O1 | −177.42 (17) | O6—C15—C16—C17 | −179.9 (2) |
C4—C10—C9—O1 | −0.7 (3) | C14—C15—C16—C17 | −0.3 (3) |
C5—C10—C9—C8 | 2.0 (3) | O8—C17—C16—O7 | −3.8 (3) |
C4—C10—C9—C8 | 178.7 (2) | C18—C17—C16—O7 | 176.4 (2) |
C9—C10—C4—O2 | −177.8 (2) | O8—C17—C16—C15 | −179.2 (2) |
C5—C10—C4—O2 | −1.3 (4) | C18—C17—C16—C15 | 0.9 (4) |
C9—C10—C4—C3 | 1.5 (3) | C14—C13—C18—C17 | 1.0 (3) |
C5—C10—C4—C3 | 178.10 (19) | C2—C13—C18—C17 | 180.0 (2) |
C2—C3—C4—O2 | 177.9 (2) | O8—C17—C18—C13 | 178.9 (2) |
O5—C3—C4—O2 | 6.3 (3) | C16—C17—C18—C13 | −1.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.82 | 1.89 | 2.609 (2) | 146 |
O8—H8A···O7 | 0.82 | 2.34 | 2.778 (3) | 114 |
O8—H8A···O6i | 0.82 | 2.20 | 2.904 (3) | 144 |
C8—H8···O2ii | 0.93 | 2.40 | 3.265 (3) | 155 |
C11—H11B···O2 | 0.96 | 2.34 | 2.967 (4) | 122 |
C14—H14···O5 | 0.93 | 2.54 | 2.936 (3) | 106 |
C20—H20B···O6 | 0.96 | 2.52 | 3.064 (4) | 116 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) x, y+1, z. |
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