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The crystal structure of 9-(3-methyl­but-2-enyl­oxy)­-7H-furo­[3,2-g]­chro­men-7-one–4-methoxy-9-(3-methyl­but-2-enyl­oxy)-7H-­furo­[3,2-g]­chromen-7-one (0.926/0.074), 0.926C16H14O4·0.074C17H16O5, is characterized by two independent imperatorin mol­ecules in the asymmetric unit, which exhibit different side-chain conformations. A small amount of phellopterin overlaps with one of the two imperatorin mol­ecules. The supramol­ecular structure is supported by C—H...O, C—H...π and π–π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103012459/bm1534sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103012459/bm1534Isup2.hkl
Contains datablock I

CCDC reference: 221083

Comment top

In continuation of our studies involving extraction of active molecules from plant species, we have examined the seeds of Angelica archangelica. The n-hexane extract yielded imperatorin, (I), a furanocoumarin that is a known dual inhibitor of cyclooxygenase and lipooxygenase (Abda et al., 2001). The spectroscopic data (UV, IR, 1H NMR and 13C NMR) were comparable to published data (Masuda et al., 1998), but a minor impurity (<10%) of phellopterin, (II), was indicated by the NMR data. Phellopterin is a potent inhibitor of the binding of diazepam to the benzodiazepine receptor (Bergendorff et al., 1997).

In the crystal, there are two molecules (A and B; Figs. 1 and 2) in the asymmetric unit. In molecule A, there is evidence of an oxymethyl group attached to atom C3A, so that the molecule corresponds to a phellopterin molecule. The refined population parameter of the O and C atoms in this oxymethyl group was 0.154 (8), indicating an imperatorin/phellopterin ratio of about 92:8.

The very low occupancy of the oxymethyl group is associated with some uncertainty in the positions of atoms C17A and O5A, but nevertheless these assignments are supported by the NMR data. Other overlapping atom positions could not be resolved, but higher displacement parameters for atoms in the side chain of molecule A, especially for the methyl C atoms, compared with molecule B, are apparent.

The two molecules differ in the conformation of the prenyloxy side chain at atom C7, as shown by the C7—O4—C12—C13 torsion angle, which is −179.0 (3)° in molecule A and 63.3 (3)° in molecule B. The atoms of the side chain in molecule B deviate more from the mean plane of the tricyclic ring system than atoms in the side chain of molecule A. In the related isoimperatorin molecule (Rajnikant et al., 1996), where the prenyloxyl side chain is at position C3, the corresponding torsion angle is −174.3 (2)°, which is similar to that in molecule A.

The imperatorin molecules are held together by three intermolecular C—H···O bonds (Table 2 (see Table 3 for Cg codes) and Fig. 3). One of these bonds joins the A molecules into a continuous chain running parallel to the a axis. Similarly, a C—H···O bond joins the B molecules into a continuous chain running in the same direction. The third bond links the two chains, thus forming R34(23) rings between two A and two B molecules. C—H···O bonds are a common feature of furocoumarin ring systems (Delettré et al., 1986; Wolska et al., 1990; Magotra et al., 1995). The supramolecular structure is also supported by edge-to-face π···H interactions (Table 2 and Fig. 4).

Completing the molecular attractions are π···π interactions (see Table 3). Fig. 5 shows the π···π interactions, denoted as thin lines, between rings of the planar tricyclic systems that pack in near parallel arrangements across centres of symmetry. Stacking interactions are also found in the furocoumarin Bergaptol (Ginderow, 1991).

Experimental top

Seeds of Angelica archangelica were purchased from B & T World Seeds Sarl, Paguignan, 34210 Olonzac, France. A voucher specimen (PH020503) has been deposited in the herbarium of the Plant and Soil Science Department, University of Aberdeen, Scotland (ABD).

The seeds (80 g) were ground using a coffee grinder and extracted sequentially with n-hexane, dichloromethane and methanol using Soxhlet apparatus. The n-hexane extract was cooled to room temperature, and the crystals were separated by filtration and dried on filter paper.

Refinement top

All non-H atoms, except atoms O5A and C17A, were refined in SHELXL97 (Sheldrick, 1997) with anisotropic displacement parameters. Because of their low occupancy, atoms O5A and C17A were refined with isotropic displacement parameters. H atoms were initially placed in calculated positions and thereafter were allowed to ride on their attached atoms, with Uiso values of 1.2 times (non-methyl) or 1.3 times (methyl) the Ueq values of the attached atom. In the final cycles of refinement, the coordinates of atom H3 were refined, but the C3A—H3A distance was restrained to be 0.95 (1) Å. The final R values are higher than normal, which may be related to the non-resolution of overlapping atom positions in molecule A.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997), COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al.,1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997).

Figures top
[Figure 1] Fig. 1. The atomic arrangement in molecule A, showing the additional –OMe group of phellopterin. Displacement ellipsoids are shown at the 50% probability level.
[Figure 2] Fig. 2. The atomic arrangement in molecule B. Displacement ellipsoids are shown at the 50% probability level.
[Figure 3] Fig. 3. The C—H···O hydrogen bonding between molecules. Disorder has been omitted. Molecules marked with an asterisk (*) or a hash (#) are transformed by (1 + x, y, z) and (−1 + x, y, z), respectively.
[Figure 4] Fig. 4. The C—H···π interactions, shown as dotted lines. Disorder has been omitted.
[Figure 5] Fig. 5. The π···π interactions, shown as thin lines, between molecules related by a centre of symmetry. Disorder has been omitted.
8-(3-methylbut-2-enyloxy)furo[3,2-g]chromen-7-one 5-methoxy-8-(3-methylbut-2-enyloxy)furo[3,2-g]chromen-7-one (0.93/0.07) top
Crystal data top
0.926C16H14O4·0.074C17H16O5Z = 4
Mr = 272.69F(000) = 572
Triclinic, P1Dx = 1.317 Mg m3
a = 11.0551 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.7236 (4) ÅCell parameters from 18828 reflections
c = 11.8718 (5) Åθ = 2.9–27.5°
α = 64.1855 (18)°µ = 0.10 mm1
β = 89.6613 (16)°T = 120 K
γ = 83.484 (2)°Needle, colourless
V = 1374.53 (9) Å30.28 × 0.04 × 0.03 mm
Data collection top
Enraf Nonius KappaCCD area detector
diffractometer
6279 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode3538 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.115
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.3°
ϕ and ω scans to fill Ewald sphereh = 1414
Absorption correction: multi-scan
(SORTAV; Blessing, 1995, 1997)
k = 1515
Tmin = 0.977, Tmax = 1.000l = 1515
24271 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.084H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.181 w = 1/[σ2(Fo2) + (0.0419P)2 + 1.433P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
6279 reflectionsΔρmax = 0.33 e Å3
380 parametersΔρmin = 0.31 e Å3
5 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.018 (3)
Crystal data top
0.926C16H14O4·0.074C17H16O5γ = 83.484 (2)°
Mr = 272.69V = 1374.53 (9) Å3
Triclinic, P1Z = 4
a = 11.0551 (4) ÅMo Kα radiation
b = 11.7236 (4) ŵ = 0.10 mm1
c = 11.8718 (5) ÅT = 120 K
α = 64.1855 (18)°0.28 × 0.04 × 0.03 mm
β = 89.6613 (16)°
Data collection top
Enraf Nonius KappaCCD area detector
diffractometer
6279 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995, 1997)
3538 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 1.000Rint = 0.115
24271 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0845 restraints
wR(F2) = 0.181H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.33 e Å3
6279 reflectionsΔρmin = 0.31 e Å3
380 parameters
Special details top

Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

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
xyzUiso*/UeqOcc. (<1)
O1A1.13925 (18)0.6947 (2)0.4713 (2)0.0367 (6)
O2A0.51082 (18)0.6718 (2)0.4648 (2)0.0389 (6)
O3A0.70783 (17)0.68416 (19)0.46151 (18)0.0264 (5)
O4A0.90161 (18)0.7372 (2)0.56338 (19)0.0325 (5)
O5A0.9711 (15)0.5223 (13)0.2425 (14)0.037 (6)*0.148 (7)
C1A1.2290 (3)0.6597 (3)0.4051 (3)0.0392 (9)
H1A1.31360.66290.41530.047*
C2A1.1829 (3)0.6213 (3)0.3265 (3)0.0376 (8)
H2A1.22720.59340.27240.045*
C3A0.9542 (3)0.6016 (3)0.2874 (3)0.0314 (7)
H3A0.967 (4)0.569 (4)0.228 (3)0.038*0.852 (7)
C4A0.7307 (3)0.5895 (3)0.2838 (3)0.0303 (7)
H4A0.73790.55920.22150.036*
C5A0.6211 (3)0.6043 (3)0.3279 (3)0.0301 (7)
H5A0.55230.58210.29780.036*
C6A0.6056 (3)0.6531 (3)0.4202 (3)0.0285 (7)
C7A0.9185 (3)0.6953 (3)0.4723 (3)0.0267 (7)
C8A0.8375 (3)0.6186 (3)0.3290 (3)0.0270 (7)
C9A1.0525 (3)0.6299 (3)0.3389 (3)0.0303 (7)
C10A1.0317 (3)0.6750 (3)0.4288 (3)0.0280 (7)
C11A0.8217 (2)0.6653 (3)0.4199 (3)0.0253 (7)
C12A0.8817 (4)0.8747 (4)0.5141 (4)0.0573 (11)
H12A0.80780.90860.45730.069*
H12B0.95200.91210.46550.069*
C13A0.8668 (4)0.9101 (4)0.6184 (4)0.0514 (10)
H13A0.93700.89280.67180.062*
C14A0.7661 (4)0.9635 (4)0.6458 (4)0.0581 (11)
C15A0.6459 (5)0.9972 (5)0.5751 (6)0.103 (2)
H15A0.62091.08920.54240.133*
H15B0.58480.95060.63110.133*
H15C0.65340.97380.50520.133*
C16A0.7636 (6)0.9902 (4)0.7575 (4)0.097 (2)
H16A0.84560.96890.79750.127*
H16B0.70750.93850.81710.127*
H16C0.73601.08100.73140.127*
C17A1.0465 (19)0.580 (2)0.1392 (18)0.037 (6)*0.148 (7)
H17A1.02770.67280.10290.048*0.148 (7)
H17B1.03110.55040.07550.048*0.148 (7)
H17C1.13250.55530.16850.048*0.148 (7)
O1B0.16965 (19)0.6659 (2)0.9841 (2)0.0460 (7)
O2B0.8041 (2)0.6494 (2)0.9888 (2)0.0447 (6)
O3B0.60398 (17)0.6584 (2)0.98392 (18)0.0280 (5)
O4B0.39576 (17)0.66394 (19)1.10752 (18)0.0293 (5)
C1B0.0875 (3)0.6711 (4)0.8938 (4)0.0555 (11)
H1B0.00200.67170.90330.067*
C2B0.1421 (3)0.6750 (4)0.7927 (4)0.0525 (11)
H2B0.10360.68000.71910.063*
C3B0.3772 (3)0.6687 (3)0.7506 (3)0.0406 (9)
H3B0.37230.67200.66940.049*
C4B0.6051 (3)0.6557 (3)0.7512 (3)0.0372 (8)
H4B0.60570.65520.67130.045*
C5B0.7105 (3)0.6504 (3)0.8089 (3)0.0381 (8)
H5B0.78470.64560.76950.046*
C6B0.7142 (3)0.6517 (3)0.9295 (3)0.0323 (7)
C7B0.3907 (3)0.6635 (3)0.9923 (3)0.0274 (7)
C8B0.4907 (3)0.6621 (3)0.8080 (3)0.0307 (7)
C9B0.2721 (3)0.6702 (3)0.8157 (3)0.0403 (9)
C10B0.2821 (3)0.6661 (3)0.9338 (3)0.0342 (8)
C11B0.4944 (3)0.6610 (3)0.9261 (3)0.0255 (7)
C12B0.3967 (3)0.7931 (3)1.0973 (3)0.0342 (8)
H12C0.46670.83111.04890.041*
H12D0.40660.78851.18210.041*
C13B0.2817 (3)0.8755 (3)1.0344 (3)0.0395 (8)
H13B0.21150.85961.08290.047*
C14B0.2654 (4)0.9682 (4)0.9194 (3)0.0501 (10)
C15B0.3647 (4)1.0117 (5)0.8287 (4)0.0776 (15)
H15D0.44270.96190.86880.101*
H15E0.36961.10240.80380.101*
H15F0.34640.99920.75450.101*
C16B0.1391 (4)1.0356 (5)0.8680 (4)0.0807 (16)
H16D0.07920.99490.92930.105*
H16E0.12091.03010.78990.105*
H16F0.13541.12550.85140.105*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0246 (12)0.0465 (15)0.0331 (12)0.0117 (10)0.0015 (9)0.0103 (11)
O2A0.0227 (12)0.0588 (16)0.0436 (14)0.0054 (10)0.0021 (10)0.0299 (12)
O3A0.0194 (10)0.0354 (13)0.0264 (11)0.0054 (9)0.0001 (8)0.0149 (10)
O4A0.0320 (12)0.0389 (14)0.0283 (12)0.0115 (10)0.0005 (9)0.0144 (10)
C1A0.0204 (16)0.043 (2)0.040 (2)0.0058 (14)0.0043 (14)0.0044 (17)
C2A0.0252 (17)0.0335 (19)0.043 (2)0.0028 (14)0.0053 (15)0.0067 (16)
C3A0.0270 (17)0.0290 (18)0.039 (2)0.0054 (13)0.0076 (14)0.0150 (15)
C4A0.0308 (17)0.0341 (19)0.0304 (17)0.0034 (14)0.0012 (13)0.0182 (15)
C5A0.0246 (16)0.0375 (19)0.0306 (17)0.0050 (13)0.0046 (13)0.0167 (15)
C6A0.0194 (15)0.0344 (18)0.0288 (17)0.0034 (13)0.0032 (13)0.0112 (14)
C7A0.0267 (16)0.0294 (17)0.0227 (16)0.0066 (13)0.0014 (12)0.0094 (14)
C8A0.0259 (16)0.0242 (17)0.0298 (17)0.0038 (12)0.0014 (13)0.0106 (14)
C9A0.0242 (16)0.0260 (17)0.0334 (18)0.0041 (13)0.0040 (13)0.0061 (14)
C10A0.0195 (15)0.0293 (17)0.0276 (17)0.0082 (12)0.0042 (12)0.0042 (14)
C11A0.0190 (15)0.0290 (17)0.0231 (15)0.0032 (12)0.0011 (12)0.0070 (13)
C12A0.088 (3)0.046 (2)0.044 (2)0.014 (2)0.019 (2)0.025 (2)
C13A0.066 (3)0.047 (2)0.045 (2)0.015 (2)0.0047 (19)0.0220 (19)
C14A0.081 (3)0.037 (2)0.054 (3)0.006 (2)0.014 (2)0.018 (2)
C15A0.087 (4)0.078 (4)0.115 (5)0.023 (3)0.005 (4)0.024 (3)
C16A0.187 (6)0.049 (3)0.065 (3)0.012 (3)0.045 (4)0.034 (3)
O1B0.0221 (12)0.0541 (16)0.0683 (17)0.0001 (10)0.0060 (11)0.0338 (14)
O2B0.0286 (13)0.0629 (17)0.0421 (15)0.0086 (11)0.0034 (11)0.0218 (13)
O3B0.0244 (11)0.0382 (13)0.0235 (11)0.0042 (9)0.0001 (9)0.0153 (10)
O4B0.0264 (11)0.0329 (13)0.0275 (12)0.0014 (9)0.0026 (9)0.0129 (10)
C1B0.033 (2)0.064 (3)0.081 (3)0.0020 (18)0.016 (2)0.043 (2)
C2B0.038 (2)0.058 (3)0.064 (3)0.0021 (18)0.024 (2)0.030 (2)
C3B0.055 (2)0.037 (2)0.0312 (19)0.0020 (16)0.0154 (16)0.0169 (16)
C4B0.054 (2)0.037 (2)0.0234 (17)0.0090 (16)0.0064 (15)0.0146 (15)
C5B0.046 (2)0.038 (2)0.0312 (19)0.0130 (16)0.0156 (16)0.0137 (16)
C6B0.0267 (17)0.0352 (19)0.0315 (18)0.0040 (13)0.0064 (14)0.0113 (15)
C7B0.0285 (16)0.0239 (17)0.0284 (17)0.0017 (12)0.0009 (13)0.0104 (14)
C8B0.0376 (18)0.0272 (18)0.0268 (17)0.0035 (14)0.0027 (14)0.0114 (14)
C9B0.0365 (19)0.039 (2)0.050 (2)0.0033 (15)0.0138 (16)0.0249 (18)
C10B0.0252 (17)0.0353 (19)0.044 (2)0.0005 (14)0.0027 (14)0.0200 (16)
C11B0.0269 (16)0.0233 (16)0.0255 (16)0.0029 (12)0.0060 (12)0.0099 (13)
C12B0.0397 (19)0.037 (2)0.0310 (18)0.0039 (15)0.0005 (14)0.0199 (15)
C13B0.044 (2)0.039 (2)0.035 (2)0.0018 (16)0.0044 (15)0.0179 (17)
C14B0.056 (2)0.043 (2)0.040 (2)0.0033 (18)0.0046 (18)0.0092 (18)
C15B0.072 (3)0.072 (3)0.057 (3)0.018 (2)0.010 (2)0.004 (2)
C16B0.071 (3)0.065 (3)0.063 (3)0.015 (2)0.002 (2)0.006 (2)
Geometric parameters (Å, º) top
O1A—C10A1.376 (3)C17A—H17B0.9800
O1A—C1A1.397 (4)C17A—H17C0.9800
O2A—C6A1.212 (3)O1B—C10B1.375 (4)
O3A—C11A1.379 (3)O1B—C1B1.386 (4)
O3A—C6A1.380 (3)O2B—C6B1.213 (4)
O4A—C7A1.372 (4)O3B—C6B1.386 (4)
O4A—C12A1.446 (4)O3B—C11B1.387 (3)
O5A—C3A1.254 (12)O4B—C7B1.372 (3)
O5A—C17A1.432 (16)O4B—C12B1.466 (4)
C1A—C2A1.325 (5)C1B—C2B1.326 (6)
C1A—H1A0.9500C1B—H1B0.9500
C2A—C9A1.445 (4)C2B—C9B1.455 (5)
C2A—H2A0.9500C2B—H2B0.9500
C3A—C9A1.390 (4)C3B—C9B1.394 (5)
C3A—C8A1.403 (4)C3B—C8B1.411 (4)
C3A—H3A0.947 (10)C3B—H3B0.9500
C4A—C5A1.341 (4)C4B—C5B1.337 (5)
C4A—C8A1.433 (4)C4B—C8B1.440 (4)
C4A—H4A0.9500C4B—H4B0.9500
C5A—C6A1.441 (4)C5B—C6B1.439 (5)
C5A—H5A0.9500C5B—H5B0.9500
C7A—C10A1.386 (4)C7B—C10B1.381 (4)
C7A—C11A1.393 (4)C7B—C11B1.390 (4)
C8A—C11A1.408 (4)C8B—C11B1.397 (4)
C9A—C10A1.391 (4)C9B—C10B1.386 (5)
C12A—C13A1.471 (5)C12B—C13B1.487 (4)
C12A—H12A0.9900C12B—H12C0.9900
C12A—H12B0.9900C12B—H12D0.9900
C13A—C14A1.324 (5)C13B—C14B1.321 (5)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C16A1.489 (6)C14B—C15B1.502 (5)
C14A—C15A1.494 (7)C14B—C16B1.512 (6)
C15A—H15A0.9800C15B—H15D0.9800
C15A—H15B0.9800C15B—H15E0.9800
C15A—H15C0.9800C15B—H15F0.9800
C16A—H16A0.9800C16B—H16D0.9800
C16A—H16B0.9800C16B—H16E0.9800
C16A—H16C0.9800C16B—H16F0.9800
C17A—H17A0.9800
C10A—O1A—C1A104.7 (3)H17A—C17A—H17B109.5
C11A—O3A—C6A121.6 (2)O5A—C17A—H17C109.5
C7A—O4A—C12A113.3 (2)H17A—C17A—H17C109.5
C3A—O5A—C17A104.4 (13)H17B—C17A—H17C109.5
C2A—C1A—O1A112.3 (3)C10B—O1B—C1B105.3 (3)
C2A—C1A—H1A123.9C6B—O3B—C11B121.6 (2)
O1A—C1A—H1A123.9C7B—O4B—C12B112.0 (2)
C1A—C2A—C9A107.0 (3)C2B—C1B—O1B112.0 (3)
C1A—C2A—H2A126.5C2B—C1B—H1B124.0
C9A—C2A—H2A126.5O1B—C1B—H1B124.0
O5A—C3A—C9A119.7 (8)C1B—C2B—C9B107.1 (3)
O5A—C3A—C8A116.8 (8)C1B—C2B—H2B126.5
C9A—C3A—C8A118.7 (3)C9B—C2B—H2B126.5
C9A—C3A—H3A120 (3)C9B—C3B—C8B118.5 (3)
C8A—C3A—H3A121 (3)C9B—C3B—H3B120.7
C5A—C4A—C8A121.2 (3)C8B—C3B—H3B120.7
C5A—C4A—H4A119.4C5B—C4B—C8B121.0 (3)
C8A—C4A—H4A119.4C5B—C4B—H4B119.5
C4A—C5A—C6A121.2 (3)C8B—C4B—H4B119.5
C4A—C5A—H5A119.4C4B—C5B—C6B121.5 (3)
C6A—C5A—H5A119.4C4B—C5B—H5B119.2
O2A—C6A—O3A115.8 (3)C6B—C5B—H5B119.2
O2A—C6A—C5A126.6 (3)O2B—C6B—O3B115.8 (3)
O3A—C6A—C5A117.6 (3)O2B—C6B—C5B126.8 (3)
O4A—C7A—C10A123.4 (3)O3B—C6B—C5B117.4 (3)
O4A—C7A—C11A121.7 (3)O4B—C7B—C10B122.2 (3)
C10A—C7A—C11A114.9 (3)O4B—C7B—C11B122.3 (3)
C3A—C8A—C11A119.9 (3)C10B—C7B—C11B115.5 (3)
C3A—C8A—C4A122.9 (3)C11B—C8B—C3B119.3 (3)
C11A—C8A—C4A117.2 (3)C11B—C8B—C4B117.5 (3)
C3A—C9A—C10A118.9 (3)C3B—C8B—C4B123.2 (3)
C3A—C9A—C2A135.9 (3)C10B—C9B—C3B119.4 (3)
C10A—C9A—C2A105.1 (3)C10B—C9B—C2B104.6 (3)
O1A—C10A—C7A124.1 (3)C3B—C9B—C2B136.1 (3)
O1A—C10A—C9A110.9 (3)O1B—C10B—C7B124.8 (3)
C7A—C10A—C9A125.0 (3)O1B—C10B—C9B111.0 (3)
O3A—C11A—C7A116.3 (3)C7B—C10B—C9B124.2 (3)
O3A—C11A—C8A121.1 (2)O3B—C11B—C7B116.0 (3)
C7A—C11A—C8A122.6 (3)O3B—C11B—C8B120.9 (3)
O4A—C12A—C13A109.3 (3)C7B—C11B—C8B123.1 (3)
O4A—C12A—H12A109.8O4B—C12B—C13B111.0 (3)
C13A—C12A—H12A109.8O4B—C12B—H12C109.4
O4A—C12A—H12B109.8C13B—C12B—H12C109.4
C13A—C12A—H12B109.8O4B—C12B—H12D109.4
H12A—C12A—H12B108.3C13B—C12B—H12D109.4
C14A—C13A—C12A126.9 (4)H12C—C12B—H12D108.0
C14A—C13A—H13A116.5C14B—C13B—C12B127.8 (3)
C12A—C13A—H13A116.5C14B—C13B—H13B116.1
C13A—C14A—C16A121.0 (5)C12B—C13B—H13B116.1
C13A—C14A—C15A125.1 (4)C13B—C14B—C15B124.8 (4)
C16A—C14A—C15A113.8 (5)C13B—C14B—C16B120.3 (4)
C14A—C15A—H15A109.5C15B—C14B—C16B114.9 (3)
C14A—C15A—H15B109.5C14B—C15B—H15D109.5
H15A—C15A—H15B109.5C14B—C15B—H15E109.5
C14A—C15A—H15C109.5H15D—C15B—H15E109.5
H15A—C15A—H15C109.5C14B—C15B—H15F109.5
H15B—C15A—H15C109.5H15D—C15B—H15F109.5
C14A—C16A—H16A109.5H15E—C15B—H15F109.5
C14A—C16A—H16B109.5C14B—C16B—H16D109.5
H16A—C16A—H16B109.5C14B—C16B—H16E109.5
C14A—C16A—H16C109.5H16D—C16B—H16E109.5
H16A—C16A—H16C109.5C14B—C16B—H16F109.5
H16B—C16A—H16C109.5H16D—C16B—H16F109.5
O5A—C17A—H17A109.5H16E—C16B—H16F109.5
O5A—C17A—H17B109.5
C10A—O1A—C1A—C2A0.3 (3)O4A—C12A—C13A—C14A111.8 (5)
O1A—C1A—C2A—C9A0.1 (4)C12A—C13A—C14A—C16A178.0 (4)
C17A—O5A—C3A—C9A63.9 (15)C12A—C13A—C14A—C15A0.7 (7)
C17A—O5A—C3A—C8A141.1 (12)C10B—O1B—C1B—C2B0.3 (4)
C8A—C4A—C5A—C6A1.6 (5)O1B—C1B—C2B—C9B0.9 (5)
C11A—O3A—C6A—O2A178.7 (3)C8B—C4B—C5B—C6B0.4 (5)
C11A—O3A—C6A—C5A2.2 (4)C11B—O3B—C6B—O2B179.7 (3)
C4A—C5A—C6A—O2A178.9 (3)C11B—O3B—C6B—C5B1.3 (4)
C4A—C5A—C6A—O3A0.0 (4)C4B—C5B—C6B—O2B178.7 (3)
C12A—O4A—C7A—C10A89.6 (4)C4B—C5B—C6B—O3B0.2 (5)
C12A—O4A—C7A—C11A92.9 (4)C12B—O4B—C7B—C10B95.1 (3)
O5A—C3A—C8A—C11A156.2 (8)C12B—O4B—C7B—C11B84.6 (3)
C9A—C3A—C8A—C11A0.9 (5)C9B—C3B—C8B—C11B1.8 (5)
O5A—C3A—C8A—C4A23.3 (9)C9B—C3B—C8B—C4B177.9 (3)
C9A—C3A—C8A—C4A178.6 (3)C5B—C4B—C8B—C11B0.8 (5)
C5A—C4A—C8A—C3A178.4 (3)C5B—C4B—C8B—C3B179.6 (3)
C5A—C4A—C8A—C11A1.0 (4)C8B—C3B—C9B—C10B0.4 (5)
O5A—C3A—C9A—C10A155.1 (8)C8B—C3B—C9B—C2B179.3 (4)
C8A—C3A—C9A—C10A0.6 (4)C1B—C2B—C9B—C10B1.1 (4)
O5A—C3A—C9A—C2A22.5 (9)C1B—C2B—C9B—C3B178.6 (4)
C8A—C3A—C9A—C2A177.1 (3)C1B—O1B—C10B—C7B179.1 (3)
C1A—C2A—C9A—C3A177.9 (4)C1B—O1B—C10B—C9B0.5 (4)
C1A—C2A—C9A—C10A0.0 (4)O4B—C7B—C10B—O1B1.8 (5)
C1A—O1A—C10A—C7A178.5 (3)C11B—C7B—C10B—O1B178.4 (3)
C1A—O1A—C10A—C9A0.3 (3)O4B—C7B—C10B—C9B177.7 (3)
O4A—C7A—C10A—O1A0.2 (5)C11B—C7B—C10B—C9B2.1 (5)
C11A—C7A—C10A—O1A177.8 (3)C3B—C9B—C10B—O1B178.8 (3)
O4A—C7A—C10A—C9A178.4 (3)C2B—C9B—C10B—O1B1.0 (4)
C11A—C7A—C10A—C9A0.8 (4)C3B—C9B—C10B—C7B1.6 (5)
C3A—C9A—C10A—O1A178.5 (3)C2B—C9B—C10B—C7B178.6 (3)
C2A—C9A—C10A—O1A0.2 (3)C6B—O3B—C11B—C7B178.0 (3)
C3A—C9A—C10A—C7A0.3 (5)C6B—O3B—C11B—C8B2.5 (4)
C2A—C9A—C10A—C7A178.6 (3)O4B—C7B—C11B—O3B0.3 (4)
C6A—O3A—C11A—C7A177.4 (3)C10B—C7B—C11B—O3B180.0 (3)
C6A—O3A—C11A—C8A2.8 (4)O4B—C7B—C11B—C8B179.2 (3)
O4A—C7A—C11A—O3A2.2 (4)C10B—C7B—C11B—C8B0.5 (4)
C10A—C7A—C11A—O3A179.8 (3)C3B—C8B—C11B—O3B178.1 (3)
O4A—C7A—C11A—C8A178.1 (3)C4B—C8B—C11B—O3B2.2 (4)
C10A—C7A—C11A—C8A0.4 (4)C3B—C8B—C11B—C7B1.4 (5)
C3A—C8A—C11A—O3A179.3 (3)C4B—C8B—C11B—C7B178.3 (3)
C4A—C8A—C11A—O3A1.2 (4)C7B—O4B—C12B—C13B63.3 (3)
C3A—C8A—C11A—C7A0.4 (4)O4B—C12B—C13B—C14B106.1 (4)
C4A—C8A—C11A—C7A179.1 (3)C12B—C13B—C14B—C15B2.1 (7)
C7A—O4A—C12A—C13A179.0 (3)C12B—C13B—C14B—C16B175.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1A—H1A···O2Ai0.952.293.232 (4)172
C1B—H1B···O2Bii0.952.403.323 (4)164
C4B—H4B···O2A0.952.593.482 (4)156
C15A—H15B···Cg(4)0.983.354.072 (7)132
C15B—H15E···Cg(3)iii0.982.923.773 (6)145
C16B—H16F···Cg(2)iii0.982.903.597 (5)129
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x+1, y+2, z+1.

Experimental details

Crystal data
Chemical formula0.926C16H14O4·0.074C17H16O5
Mr272.69
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)11.0551 (4), 11.7236 (4), 11.8718 (5)
α, β, γ (°)64.1855 (18), 89.6613 (16), 83.484 (2)
V3)1374.53 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.28 × 0.04 × 0.03
Data collection
DiffractometerEnraf Nonius KappaCCD area detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995, 1997)
Tmin, Tmax0.977, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
24271, 6279, 3538
Rint0.115
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.084, 0.181, 1.05
No. of reflections6279
No. of parameters380
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.31

Computer programs: DENZO (Otwinowski & Minor, 1997), COLLECT (Hooft, 1998), DENZO and COLLECT, SIR97 (Altomare et al.,1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).

Selected geometric parameters (Å, º) top
O4A—C12A1.446 (4)O4B—C12B1.466 (4)
C14A—C16A1.489 (6)C14B—C16B1.512 (6)
C3A—C9A—C2A135.9 (3)C3B—C9B—C2B136.1 (3)
O4A—C12A—C13A109.3 (3)O4B—C12B—C13B111.0 (3)
C7A—O4A—C12A—C13A179.0 (3)C7B—O4B—C12B—C13B63.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1A—H1A···O2Ai.952.293.232 (4)172
C1B—H1B···O2Bii.952.403.323 (4)164
C4B—H4B···O2A.952.593.482 (4)156
C15A—H15B···Cg(4).983.354.072 (7)132
C15B—H15E···Cg(3)iii.982.923.773 (6)145
C16B—H16F···Cg(2)iii.982.903.597 (5)129
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x+1, y+2, z+1.
π - π interactions (Å, °) top
Cg(I)Cg(J)symmetryCg···Cgdihedral_angleinterplanaroffset
132 − x,1 − y,1 − z3.560 (2)3.33.326 (3)1.27
152 − x,1 − y,1 − z3.550 (2)1.93.375 (3)1.10
461 − x,1 − y,2 − z3.682 (2)1.73.371 (3)1.48
552 − x,1 − y,1 − z3.534 (2)0.03.390 (3)1.00
Cg is the centre of gravity of the rings: 1: furan (molecule A), 2: furan (molecule B), 3: pyrone (molecule A), 4: pyrone (molecule B), 5: benzene (molecule A), 6: benzene (molecule B).
 

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