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The title compound, C17H16O5, an (E)-1-(4,6-dihydroxy-2,3-dimeth­oxy­phen­yl)-3-phenyl­prop-2-en-1-one, was isolated from a plant of genus Cryptocarya costata. The mol­ecule adopts a trans configuration with respect to the positions of the benzene ring and the dihydroxy­dimethoxy­benzaldehyde fragment about the olefinic C=C double bond. The mol­ecules are linked by inter­molecular hydrogen bonds to form ribbons extending parallel to the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680504047X/at6060sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680504047X/at6060Isup2.hkl
Contains datablock I

CCDC reference: 296511

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.053
  • wR factor = 0.130
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
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 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

A number of chalcones containing hydroxyl groups at C(2'), C(2',4') or C(2',4) have been known to be potential as therapeutic agents against infections with methicilin-resistant Staphylococcus aureus strains (Alcaraz et al., 2000). Therefore, some chalcone derivatives have been successfully synthesized including 2',4'-dihydroxy-5',6'-dimethoxychalcone (I) (Bhaskar & Seshadri, 1974). However, only a few structures of naturally occurring chalcones isolated from plants have been reported. Some examples are 2',6'-dihydroxy-4,4'-dimethoxychalcone (II) from the plant Pityrogramma chrysophylla (Nilsson, 1961; Schmalle et al., 1990), Flemiculosin (III) from the leaves of Flemingia fruticolose (Bhattacharyya et al., 1999) and (E)-1-(2-hydroxy-3-(4-dimethoxyphenyl)prop-2-en-one (IV) (Krishna et al., 2005). In the course of our study on the secondary metabolites from Cryptocarya sp. growing in Indonesia, suitable crystals of (I) for X-ray investigation were obtained.

As in most substituted chalcones, the molecule of the title compound (I) is not planar. The substituted benzene ring (C1'-C6')/O2/O3/O4/O5 is essentially planar with maximum deviation of 0.054 (2) Å for atom O2 from the least square plane. It is inclined by 28.22 (10)° to the propenylbenzene fragment [C1–C9] (maximum deviation 0.022 (2) Å at atom C8). The O–Me bonds, O2–C10 and O3–C11, are perpendicular to the benzene C1'–C6' plane with torsion angles C10–O2–C6'–C5' and C11–O3–C5'–C6' of 88.5 (3) and 65.93 (3)°, respectively. The carbonyl group, C9O1, is in a cis configuration with respect to the olefenic C7C8 double bond, a typical chalcone compound.

The bond lengths and angles of the molecule are in normal ranges (Table 1) and in agreement with all the analogues with slight variation on the CO bond length. The C9O1 bond length is slightly shorter than that in (II) and (IV) [1.264 (3) and 1.2538 (17) Å, respectively]. The presence of five intramolecular hydrogen bonds viz. O4–H4B···O3, O5–H5B···O1, C7–H7A···O1, C8–H8A···O2 and C11–H11C···O2 (Table 2) may contribute to the stability and planarity of the molecule. In the structure, the molecules are linked by intermolecular hydrogen bonds (symmetry codes as given in Table 2) forming ribbons extended parallel to b axis (Fig. 2).

Experimental top

Barks from the tree Cryptocarya costata Bl. were collected from The National Garden of Leralindu, Central Sulawesi, Indonesia. The voucher specimen (E-377L) was deposited at the herbarium of Faculty of Sciences, University of Tadulako, Central Sulawesi. The powdered dried tree barks (2.5 kg) of C. costata were macerated with methanol at room temperature for 24 h. The mixture was filtered and the methanol filtrate was evaporated under reduced pressure to give a concentrated methanol extract. To the extract distilled water was added, and the aqueous methanol extract was partitioned into CHCl3 and ethyl acetate to give CHCl3 (140 g) and ethyl acetate (40 g) soluble fractions. A portion (20 g) of the CHCl3 fraction was fractionated using column vacuum chromatography (silica gel, eluted with n-hexane–ethyl acetate = 9:1–1:1) to give six major fractions AF. Repeated purification of fraction C (230 g) by radial chromatography (n-hexane–EtOAc = 7:3) gave compound (I). Recrystallization from methanol afforded yellow crystals (50 g) with melting point 440–442 K.

Refinement top

H atoms were located in the difference map and repositioned geometrically with C–H = 0.93 − 0.96 Å and O–H = 0.86 Å. They were constrained to ride on their parent atoms, with Uiso(H) = 1.2 (1.5 for CH3 and OH) times Ueq(C,O).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The dashed lines indicate the intramolecular O–H···O and C–H···O hydrogen bonds.
[Figure 2] Fig. 2. A packing diagram for (I). The intermolecular C–H···O and O–H···O hydrogen bonding interactions are shown as dashed lines.
2',4'-Dihydroxy-5',6'-dimethoxychalcone top
Crystal data top
C17H16O5F(000) = 1264
Mr = 300.30Dx = 1.353 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3566 reflections
a = 12.360 (2) Åθ = 2.0–25.5°
b = 7.1688 (14) ŵ = 0.10 mm1
c = 33.275 (6) ÅT = 298 K
V = 2948.3 (10) Å3Block, yellow
Z = 80.48 × 0.45 × 0.19 mm
Data collection top
Bruker SMART APEX area-detector
diffractometer
2747 independent reflections
Radiation source: fine-focus sealed tube2137 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 83.66 pixels mm-1θmax = 25.5°, θmin = 2.0°
ω scansh = 1414
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
k = 88
Tmin = 0.953, Tmax = 0.981l = 3340
14651 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0545P)2 + 0.9791P]
where P = (Fo2 + 2Fc2)/3
2747 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C17H16O5V = 2948.3 (10) Å3
Mr = 300.30Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 12.360 (2) ŵ = 0.10 mm1
b = 7.1688 (14) ÅT = 298 K
c = 33.275 (6) Å0.48 × 0.45 × 0.19 mm
Data collection top
Bruker SMART APEX area-detector
diffractometer
2747 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
2137 reflections with I > 2σ(I)
Tmin = 0.953, Tmax = 0.981Rint = 0.032
14651 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 1.11Δρmax = 0.18 e Å3
2747 reflectionsΔρmin = 0.15 e Å3
199 parameters
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.18787 (12)0.0964 (3)0.36742 (5)0.0636 (5)
O20.52405 (11)0.1270 (2)0.38143 (4)0.0534 (4)
O30.60992 (11)0.2219 (3)0.45505 (4)0.0577 (5)
O40.47337 (12)0.2885 (3)0.51833 (4)0.0717 (6)
H4B0.53960.28300.51750.108*
O50.16773 (11)0.1899 (2)0.43929 (5)0.0591 (5)
H5B0.14880.15460.41690.089*
C20.30111 (18)0.0632 (3)0.22705 (7)0.0536 (6)
H2A0.23500.11970.23250.064*
C30.3440 (2)0.0750 (4)0.18884 (7)0.0606 (7)
H3A0.30750.14140.16900.073*
C40.4400 (2)0.0106 (3)0.18010 (7)0.0576 (6)
H4A0.46850.00390.15430.069*
C50.49407 (19)0.1066 (3)0.20968 (7)0.0552 (6)
H5A0.55920.16540.20370.066*
C60.45255 (17)0.1165 (3)0.24799 (7)0.0494 (5)
H6A0.49040.18090.26780.059*
C10.35465 (16)0.0314 (3)0.25750 (6)0.0428 (5)
C70.30642 (17)0.0404 (3)0.29747 (6)0.0457 (5)
H7A0.23970.01780.30050.055*
C80.34651 (17)0.1216 (3)0.32986 (6)0.0480 (5)
H8A0.41380.17940.32830.058*
C90.28749 (16)0.1230 (3)0.36831 (6)0.0470 (5)
C1'0.34106 (16)0.1603 (3)0.40662 (6)0.0419 (5)
C6'0.45453 (15)0.1668 (3)0.41239 (6)0.0419 (5)
C5'0.49921 (16)0.2141 (3)0.44887 (6)0.0461 (5)
C4'0.43233 (17)0.2486 (3)0.48180 (6)0.0508 (6)
C3'0.32199 (16)0.2408 (4)0.47744 (6)0.0523 (6)
H3B0.27750.26600.49930.063*
C2'0.27679 (16)0.1961 (3)0.44104 (6)0.0449 (5)
C110.66396 (19)0.3645 (5)0.43294 (7)0.0740 (8)
H11A0.74000.36080.43880.111*
H11B0.63530.48400.44040.111*
H11C0.65300.34470.40470.111*
C100.5553 (2)0.0645 (5)0.37975 (9)0.0874 (9)
H10A0.60370.08330.35760.131*
H10B0.49210.14090.37620.131*
H10C0.59090.09830.40430.131*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0402 (9)0.0979 (14)0.0527 (10)0.0085 (8)0.0023 (7)0.0049 (9)
O20.0430 (8)0.0768 (12)0.0403 (8)0.0004 (8)0.0073 (6)0.0037 (7)
O30.0355 (8)0.0945 (13)0.0430 (9)0.0035 (8)0.0019 (6)0.0104 (8)
O40.0476 (9)0.1305 (17)0.0369 (8)0.0046 (10)0.0006 (7)0.0042 (9)
O50.0349 (8)0.0897 (13)0.0526 (9)0.0000 (8)0.0037 (7)0.0027 (8)
C20.0517 (13)0.0544 (14)0.0546 (14)0.0120 (11)0.0028 (10)0.0007 (11)
C30.0718 (16)0.0651 (17)0.0449 (13)0.0077 (13)0.0078 (11)0.0078 (11)
C40.0701 (15)0.0585 (15)0.0442 (13)0.0018 (13)0.0054 (11)0.0004 (11)
C50.0531 (14)0.0549 (15)0.0577 (14)0.0072 (11)0.0079 (11)0.0006 (12)
C60.0471 (12)0.0525 (13)0.0488 (12)0.0054 (10)0.0013 (10)0.0044 (11)
C10.0443 (11)0.0412 (12)0.0428 (12)0.0003 (9)0.0024 (9)0.0017 (9)
C70.0415 (11)0.0471 (13)0.0483 (13)0.0030 (10)0.0004 (9)0.0021 (10)
C80.0408 (11)0.0590 (14)0.0442 (12)0.0056 (10)0.0030 (9)0.0057 (11)
C90.0391 (12)0.0545 (14)0.0473 (12)0.0019 (10)0.0014 (9)0.0019 (10)
C1'0.0396 (11)0.0478 (13)0.0384 (11)0.0008 (9)0.0020 (9)0.0049 (9)
C6'0.0387 (11)0.0526 (13)0.0343 (10)0.0017 (9)0.0049 (8)0.0061 (9)
C5'0.0351 (11)0.0638 (15)0.0394 (11)0.0010 (10)0.0011 (9)0.0083 (10)
C4'0.0465 (12)0.0708 (16)0.0351 (11)0.0029 (11)0.0014 (10)0.0054 (10)
C3'0.0428 (12)0.0748 (16)0.0393 (12)0.0001 (11)0.0091 (9)0.0015 (11)
C2'0.0348 (11)0.0548 (14)0.0451 (12)0.0010 (9)0.0028 (9)0.0069 (10)
C110.0515 (15)0.116 (2)0.0543 (15)0.0231 (15)0.0008 (12)0.0133 (15)
C100.080 (2)0.099 (2)0.083 (2)0.0330 (18)0.0161 (16)0.0099 (18)
Geometric parameters (Å, º) top
O1—C91.246 (2)C1—C71.459 (3)
O2—C6'1.371 (2)C7—C81.321 (3)
O2—C101.428 (3)C7—H7A0.9300
O3—C5'1.385 (2)C8—C91.473 (3)
O3—C111.426 (3)C8—H8A0.9300
O4—C4'1.348 (2)C9—C1'1.461 (3)
O4—H4B0.8200C1'—C6'1.416 (3)
O5—C2'1.350 (2)C1'—C2'1.417 (3)
O5—H5B0.8200C6'—C5'1.376 (3)
C2—C31.380 (3)C5'—C4'1.395 (3)
C2—C11.387 (3)C4'—C3'1.373 (3)
C2—H2A0.9300C3'—C2'1.372 (3)
C3—C41.367 (3)C3'—H3B0.9300
C3—H3A0.9300C11—H11A0.9600
C4—C51.375 (3)C11—H11B0.9600
C4—H4A0.9300C11—H11C0.9600
C5—C61.376 (3)C10—H10A0.9600
C5—H5A0.9300C10—H10B0.9600
C6—C11.392 (3)C10—H10C0.9600
C6—H6A0.9300
C6'—O2—C10113.48 (19)C6'—C1'—C2'116.09 (18)
C5'—O3—C11114.54 (18)C6'—C1'—C9124.96 (18)
C4'—O4—H4B109.5C2'—C1'—C9118.95 (18)
C2'—O5—H5B109.5O2—C6'—C5'117.55 (17)
C3—C2—C1121.3 (2)O2—C6'—C1'120.79 (18)
C3—C2—H2A119.3C5'—C6'—C1'121.66 (18)
C1—C2—H2A119.3C6'—C5'—O3122.50 (18)
C4—C3—C2120.1 (2)C6'—C5'—C4'119.92 (19)
C4—C3—H3A119.9O3—C5'—C4'117.53 (18)
C2—C3—H3A119.9O4—C4'—C3'118.56 (19)
C3—C4—C5119.6 (2)O4—C4'—C5'121.53 (19)
C3—C4—H4A120.2C3'—C4'—C5'119.9 (2)
C5—C4—H4A120.2C2'—C3'—C4'120.5 (2)
C4—C5—C6120.5 (2)C2'—C3'—H3B119.7
C4—C5—H5A119.7C4'—C3'—H3B119.7
C6—C5—H5A119.7O5—C2'—C3'116.89 (18)
C5—C6—C1120.8 (2)O5—C2'—C1'121.27 (19)
C5—C6—H6A119.6C3'—C2'—C1'121.83 (19)
C1—C6—H6A119.6O3—C11—H11A109.5
C2—C1—C6117.59 (19)O3—C11—H11B109.5
C2—C1—C7119.51 (19)H11A—C11—H11B109.5
C6—C1—C7122.90 (19)O3—C11—H11C109.5
C8—C7—C1127.6 (2)H11A—C11—H11C109.5
C8—C7—H7A116.2H11B—C11—H11C109.5
C1—C7—H7A116.2O2—C10—H10A109.5
C7—C8—C9121.7 (2)O2—C10—H10B109.5
C7—C8—H8A119.1H10A—C10—H10B109.5
C9—C8—H8A119.1O2—C10—H10C109.5
O1—C9—C1'119.76 (19)H10A—C10—H10C109.5
O1—C9—C8117.89 (19)H10B—C10—H10C109.5
C1'—C9—C8122.32 (18)
C1—C2—C3—C41.4 (4)C2'—C1'—C6'—C5'3.1 (3)
C2—C3—C4—C50.7 (4)C9—C1'—C6'—C5'175.9 (2)
C3—C4—C5—C60.3 (4)O2—C6'—C5'—O30.2 (3)
C4—C5—C6—C10.7 (4)C1'—C6'—C5'—O3179.7 (2)
C3—C2—C1—C61.0 (3)O2—C6'—C5'—C4'177.4 (2)
C3—C2—C1—C7180.0 (2)C1'—C6'—C5'—C4'3.1 (3)
C5—C6—C1—C20.0 (3)C11—O3—C5'—C6'65.9 (3)
C5—C6—C1—C7179.0 (2)C11—O3—C5'—C4'116.8 (2)
C2—C1—C7—C8179.0 (2)C6'—C5'—C4'—O4177.5 (2)
C6—C1—C7—C82.0 (4)O3—C5'—C4'—O40.2 (3)
C1—C7—C8—C9178.7 (2)C6'—C5'—C4'—C3'2.0 (4)
C7—C8—C9—O120.8 (3)O3—C5'—C4'—C3'179.3 (2)
C7—C8—C9—C1'161.3 (2)O4—C4'—C3'—C2'178.4 (2)
O1—C9—C1'—C6'170.7 (2)C5'—C4'—C3'—C2'1.1 (4)
C8—C9—C1'—C6'11.5 (3)C4'—C3'—C2'—O5179.5 (2)
O1—C9—C1'—C2'10.3 (3)C4'—C3'—C2'—C1'1.3 (4)
C8—C9—C1'—C2'167.6 (2)C6'—C1'—C2'—O5178.6 (2)
C10—O2—C6'—C5'88.5 (3)C9—C1'—C2'—O52.3 (3)
C10—O2—C6'—C1'92.0 (3)C6'—C1'—C2'—C3'2.3 (3)
C2'—C1'—C6'—O2177.39 (19)C9—C1'—C2'—C3'176.8 (2)
C9—C1'—C6'—O23.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4B···O30.822.292.741 (2)115
O5—H5B···O10.821.772.496 (2)147
C7—H7A···O10.932.462.780 (3)100
C8—H8A···O20.932.262.786 (3)115
C11—H11C···O20.962.362.971 (3)121
O4—H4B···O5i0.822.152.790 (2)135
C3—H3B···O3ii0.932.573.462 (3)161
C11—H11B···O4iii0.962.523.420 (4)156
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x1/2, y+1/2, z+1; (iii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC17H16O5
Mr300.30
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)298
a, b, c (Å)12.360 (2), 7.1688 (14), 33.275 (6)
V3)2948.3 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.48 × 0.45 × 0.19
Data collection
DiffractometerBruker SMART APEX area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.953, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
14651, 2747, 2137
Rint0.032
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.130, 1.11
No. of reflections2747
No. of parameters199
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.15

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top
O1—C91.246 (2)O3—C111.426 (3)
O2—C6'1.371 (2)O4—C4'1.348 (2)
O2—C101.428 (3)O5—C2'1.350 (2)
O3—C5'1.385 (2)C7—C81.321 (3)
C10—O2—C6'—C1'92.0 (3)C11—O3—C5'—C4'116.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4B···O30.822.292.741 (2)115
O5—H5B···O10.821.772.496 (2)147
C7—H7A···O10.932.462.780 (3)100
C8—H8A···O20.932.262.786 (3)115
C11—H11C···O20.962.362.971 (3)121
O4—H4B···O5i0.822.152.790 (2)135
C3'—H3B···O3ii0.932.573.462 (3)161
C11—H11B···O4iii0.962.523.420 (4)156
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x1/2, y+1/2, z+1; (iii) x+1, y+1, z+1.
 

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