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The title compound, C17H18O5, was isolated from the leaves of Rauwenhoffia siamensis Scheff. There are two crystallographically independent mol­ecules in the asymmetric unit. The dihedral angle between the two benzene rings is 80.81 (7)° in one mol­ecule and 65.89 (7)° in the other. The symmetry-related mol­ecules are linked via O—H...O inter­molecular hydrogen bonds to form chains along [201].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028291/ci6648sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028291/ci6648Isup2.hkl
Contains datablock I

CCDC reference: 287513

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.054
  • wR factor = 0.156
  • Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.61 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O5A PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C2A PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3A PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6A
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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

Rauwenhoffia siamensis Scheff. belongs to the family of Annonaceae, which is widely distributed in Thailand, Malaysia and Indonesia. R. siamensis has a local Thai name, Nom Maew, and has been used for biofragrance (Chulalaksananukul et al., 1998). The title compound, (I), was isolated from the leaves of R. siamensis, which were collected from Songkhla province in the southern part of Thailand. The naringin dihydrochalcone, which is a derivative of compound (I), was known as a sweetener (Shin et al., 1998 or 1995?). As part of our systematic studies on chemical constituents of Thai medicinal plants (Chantrapromma et al., 2003, 2004, 2005; Boonnak et al., 2005; Thongdeeying et al., 2005; Fun et al., 2005), we have undertaken the X-ray crystal structure analysis of (I) in order to establish its molecular structure and relative stereochemistry.

The crystal structure of (I) was previously reported by De Matheus et al. (1991) in the monoclinic space group P21/c, with a = 4.856 (3), b = 28.896 (7), c = 10.776 (3) Å, β = 98.04 (4)° and Z = 4. In the present work, the compound crystallized again in the monoclinic space group P21/c, but with different cell parameters and Z = 8.

The asymmetric unit of (I) contains two molecules, A and B, in which the orientation of the C1–C6 benzene ring with respect to the central –C7—C8—C9O3 linkage is different (Fig. 1). The corresponding bond lengths and angles of these two molecules agree with each other and show normal values (Allen et al., 1987), and are comparable to those observed in the other monoclinic polymorph (De Matheus et al., 1991) and a closely related structure (Shin et al., 1998 or 1995?). In molecule A, the C1–C6 and C10–C15 benzene rings are oriented at angles of 83.79 (8) and 8.69 (11)° [65.15 (9) and 5.74 (12)° in molecule B] with respect to the C7—C8—C9O3 plane. The dihedral angle between the two benzene rings is 80.81 (7)° in molecule A and 65.89 (7)° in molecule B, compared to 81.49 (9)° in the other polymorph (De Matheus et al., 1991). In both molecules A and B, the methoxy groups are coplanar with the attached benzene rings. The molecular structure is stabilized by intramolecular O—H···O hydrogen bonds (Table 2). The symmetry-related molecules are linked into chains along [101] by O—H···O intermolecular hydrogen bonds (Fig. 2).

Experimental top

Air-dried leaves of R. siamensis were ground and extracted with CH2Cl2 at room temperature. The residue obtained after evaporation of the solvent was repeatedly subjected to column chromatography over silica gel to afford (I). Single crystals of (I) were obtained by recrystallization from a CH2Cl2–CH3OH (8:2 (v/v) solvent system (m.p. 442–443 K).

Refinement top

H atoms were placed in calculated positions, with O—H = 0.82 Å and C—H = 0.93–0.97 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for hydroxyl and methyl H atoms and 1.2Ueq for the remaining H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering.
[Figure 2] Fig. 2. The crystal packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines.
1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-methoxyphenyl)propan-1-one top
Crystal data top
C17H18O5F(000) = 1280
Mr = 302.31Dx = 1.342 Mg m3
Monoclinic, P21/cMelting point = 442–443 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 9.7048 (2) ÅCell parameters from 7172 reflections
b = 28.9048 (5) Åθ = 1.4–27.9°
c = 13.4920 (2) ŵ = 0.10 mm1
β = 127.770 (1)°T = 273 K
V = 2991.72 (10) Å3Plate, colourless
Z = 80.50 × 0.42 × 0.07 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
7172 independent reflections
Radiation source: fine-focus sealed tube3709 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 8.33 pixels mm-1θmax = 27.9°, θmin = 1.4°
ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 3829
Tmin = 0.952, Tmax = 0.993l = 1417
26484 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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0649P)2 + 0.2747P]
where P = (Fo2 + 2Fc2)/3
7130 reflections(Δ/σ)max < 0.001
405 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C17H18O5V = 2991.72 (10) Å3
Mr = 302.31Z = 8
Monoclinic, P21/cMo Kα radiation
a = 9.7048 (2) ŵ = 0.10 mm1
b = 28.9048 (5) ÅT = 273 K
c = 13.4920 (2) Å0.50 × 0.42 × 0.07 mm
β = 127.770 (1)°
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
7172 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
3709 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 0.993Rint = 0.037
26484 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.156H-atom parameters constrained
S = 1.03Δρmax = 0.18 e Å3
7130 reflectionsΔρmin = 0.21 e Å3
405 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.

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*/Ueq
O1A0.01879 (16)0.32902 (4)0.40421 (12)0.0545 (4)
H1A0.11770.31830.35790.065*
O2A0.56058 (15)0.28692 (4)0.69543 (12)0.0514 (4)
H2A0.62570.26450.72790.062*
O3A0.64501 (15)0.20324 (4)0.73696 (11)0.0501 (3)
O4A0.12998 (16)0.16833 (4)0.47857 (12)0.0559 (4)
O5A0.4342 (3)0.07587 (5)0.76468 (18)0.0951 (6)
C1A0.5735 (3)0.02634 (8)0.6925 (2)0.0821 (8)
H1B0.61010.03330.64460.098*
C2A0.5280 (4)0.01844 (8)0.6954 (3)0.0941 (9)
H2B0.53440.04120.64970.113*
C3A0.4734 (3)0.02997 (7)0.7651 (2)0.0642 (6)
C4A0.4624 (3)0.00402 (7)0.8301 (2)0.0655 (6)
H4A0.42420.00290.87700.079*
C5A0.5085 (3)0.04893 (7)0.8258 (2)0.0632 (6)
H5A0.50000.07180.87030.076*
C6A0.5660 (2)0.06090 (6)0.75859 (19)0.0498 (5)
C7A0.6136 (2)0.11029 (6)0.75536 (19)0.0532 (5)
H7A0.69410.11060.73530.064*
H7B0.67220.12400.83770.064*
C8A0.4545 (2)0.13902 (6)0.65937 (16)0.0437 (4)
H8A0.40650.12770.57630.052*
H8B0.36690.13450.67170.052*
C9A0.4895 (2)0.19000 (6)0.66480 (16)0.0392 (4)
C10A0.3516 (2)0.22437 (6)0.59219 (15)0.0360 (4)
C11A0.3950 (2)0.27232 (6)0.61200 (15)0.0374 (4)
C12A0.2700 (2)0.30648 (6)0.54863 (16)0.0426 (4)
H12A0.30200.33750.56410.051*
C13A0.0975 (2)0.29413 (6)0.46230 (16)0.0399 (4)
C14A0.0476 (2)0.24795 (6)0.43662 (15)0.0403 (4)
H14A0.06900.24020.37660.048*
C15A0.1712 (2)0.21384 (6)0.50013 (15)0.0384 (4)
C16A0.0448 (2)0.15516 (6)0.37805 (18)0.0563 (5)
H16A0.05220.12210.37080.084*
H16B0.07740.16840.30110.084*
H16C0.12210.16620.39470.084*
C17A0.4040 (3)0.09008 (8)0.8492 (2)0.0821 (8)
H17A0.38600.12290.84270.123*
H17B0.30240.07470.82970.123*
H17C0.50300.08230.93300.123*
O1B0.46198 (16)0.32938 (4)0.39931 (13)0.0542 (4)
H1C0.36290.31890.35130.065*
O2B1.04122 (15)0.28501 (4)0.68117 (12)0.0524 (4)
H2C1.10530.26230.71110.063*
O3B1.12152 (15)0.20107 (4)0.72066 (12)0.0530 (4)
O4B0.60078 (16)0.16824 (4)0.47141 (12)0.0565 (4)
O5B0.9202 (2)0.07618 (5)0.76733 (16)0.0797 (5)
C1B0.9623 (3)0.02773 (8)0.6389 (2)0.0739 (7)
H1D0.93370.03710.56240.089*
C2B0.9220 (3)0.01670 (8)0.6512 (2)0.0748 (7)
H2D0.86590.03680.58300.090*
C3B0.9646 (3)0.03136 (7)0.7639 (2)0.0606 (6)
C4B1.0469 (3)0.00131 (7)0.8635 (2)0.0689 (6)
H4B1.07710.01080.94040.083*
C5B1.0845 (3)0.04314 (7)0.8490 (2)0.0687 (6)
H5B1.13920.06320.91710.082*
C6B1.0446 (3)0.05875 (7)0.7384 (2)0.0584 (6)
C7B1.0884 (3)0.10794 (7)0.7272 (2)0.0663 (6)
H7C1.16270.12180.81000.080*
H7D1.15300.10730.69390.080*
C8B0.9278 (2)0.13759 (6)0.64330 (17)0.0472 (5)
H8C0.86570.12720.55740.057*
H8D0.85170.13300.66630.057*
C9B0.9654 (2)0.18851 (6)0.64964 (16)0.0405 (4)
C10B0.8286 (2)0.22322 (6)0.58025 (15)0.0381 (4)
C11B0.8745 (2)0.27111 (6)0.60042 (16)0.0393 (4)
C12B0.7514 (2)0.30562 (6)0.54034 (16)0.0431 (4)
H12B0.78530.33650.55660.052*
C13B0.5772 (2)0.29413 (6)0.45578 (16)0.0402 (4)
C14B0.5243 (2)0.24821 (6)0.43030 (16)0.0410 (4)
H14B0.40680.24090.37220.049*
C15B0.6472 (2)0.21347 (6)0.49171 (15)0.0389 (4)
C16B0.4246 (2)0.15593 (7)0.37094 (18)0.0577 (6)
H16D0.41420.12290.36400.087*
H16E0.39320.16870.29390.087*
H16F0.34840.16800.38750.087*
C17B0.9454 (3)0.09108 (8)0.8776 (2)0.0872 (8)
H17D0.91420.12310.86950.131*
H17E0.87340.07300.88940.131*
H17F1.06550.08710.94850.131*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0351 (7)0.0413 (7)0.0646 (9)0.0027 (6)0.0190 (7)0.0049 (6)
O2A0.0296 (7)0.0460 (7)0.0557 (8)0.0054 (6)0.0144 (6)0.0009 (6)
O3A0.0291 (7)0.0488 (8)0.0528 (8)0.0000 (6)0.0152 (6)0.0053 (6)
O4A0.0367 (7)0.0380 (7)0.0549 (8)0.0037 (6)0.0086 (6)0.0017 (6)
O5A0.1403 (17)0.0407 (9)0.1297 (16)0.0085 (9)0.0957 (15)0.0057 (9)
C1A0.120 (2)0.0539 (15)0.114 (2)0.0141 (14)0.093 (2)0.0099 (14)
C2A0.157 (3)0.0472 (15)0.127 (2)0.0068 (15)0.112 (2)0.0068 (15)
C3A0.0737 (16)0.0384 (12)0.0804 (16)0.0009 (10)0.0473 (14)0.0003 (11)
C4A0.0778 (16)0.0529 (13)0.0786 (16)0.0036 (11)0.0544 (14)0.0001 (12)
C5A0.0782 (16)0.0425 (12)0.0744 (15)0.0034 (11)0.0496 (14)0.0046 (11)
C6A0.0374 (10)0.0429 (11)0.0575 (13)0.0074 (8)0.0232 (10)0.0083 (10)
C7A0.0405 (11)0.0452 (11)0.0650 (13)0.0037 (9)0.0277 (10)0.0076 (10)
C8A0.0375 (10)0.0427 (10)0.0449 (11)0.0013 (8)0.0222 (9)0.0043 (8)
C9A0.0343 (10)0.0453 (11)0.0353 (10)0.0003 (8)0.0200 (8)0.0019 (8)
C10A0.0309 (9)0.0381 (10)0.0342 (9)0.0000 (7)0.0175 (8)0.0019 (8)
C11A0.0296 (9)0.0422 (10)0.0352 (9)0.0053 (8)0.0172 (8)0.0008 (8)
C12A0.0378 (10)0.0369 (10)0.0458 (11)0.0038 (8)0.0218 (9)0.0002 (8)
C13A0.0346 (10)0.0416 (11)0.0391 (10)0.0035 (8)0.0204 (8)0.0045 (8)
C14A0.0292 (9)0.0416 (10)0.0363 (10)0.0027 (8)0.0130 (8)0.0011 (8)
C15A0.0350 (10)0.0370 (10)0.0352 (10)0.0030 (8)0.0175 (8)0.0008 (8)
C16A0.0414 (11)0.0478 (11)0.0509 (12)0.0117 (9)0.0136 (10)0.0068 (9)
C17A0.0711 (16)0.0570 (15)0.108 (2)0.0067 (12)0.0495 (16)0.0123 (14)
O1B0.0378 (7)0.0408 (7)0.0642 (9)0.0027 (6)0.0211 (7)0.0042 (6)
O2B0.0312 (7)0.0487 (8)0.0556 (8)0.0063 (6)0.0156 (6)0.0010 (7)
O3B0.0331 (7)0.0511 (8)0.0589 (8)0.0007 (6)0.0200 (7)0.0074 (6)
O4B0.0378 (7)0.0374 (7)0.0602 (9)0.0054 (6)0.0126 (7)0.0030 (6)
O5B0.0965 (13)0.0417 (9)0.1014 (13)0.0068 (8)0.0608 (11)0.0011 (8)
C1B0.0860 (18)0.0628 (15)0.0738 (16)0.0037 (13)0.0494 (15)0.0118 (13)
C2B0.0896 (18)0.0537 (14)0.0756 (17)0.0033 (13)0.0478 (15)0.0064 (12)
C3B0.0581 (13)0.0404 (12)0.0808 (16)0.0031 (10)0.0414 (13)0.0041 (11)
C4B0.0762 (16)0.0519 (13)0.0712 (15)0.0059 (12)0.0413 (14)0.0055 (12)
C5B0.0685 (15)0.0487 (13)0.0740 (16)0.0065 (11)0.0360 (13)0.0003 (12)
C6B0.0466 (12)0.0454 (12)0.0751 (15)0.0059 (9)0.0331 (12)0.0099 (11)
C7B0.0465 (12)0.0483 (12)0.0934 (17)0.0050 (10)0.0373 (12)0.0170 (11)
C8B0.0390 (10)0.0448 (11)0.0542 (12)0.0007 (8)0.0266 (10)0.0061 (9)
C9B0.0350 (10)0.0474 (11)0.0378 (10)0.0008 (8)0.0216 (8)0.0031 (8)
C10B0.0325 (9)0.0404 (10)0.0363 (10)0.0009 (8)0.0185 (8)0.0007 (8)
C11B0.0329 (9)0.0425 (10)0.0373 (10)0.0064 (8)0.0188 (8)0.0013 (8)
C12B0.0402 (10)0.0370 (10)0.0443 (11)0.0044 (8)0.0219 (9)0.0000 (8)
C13B0.0379 (10)0.0399 (10)0.0392 (10)0.0017 (8)0.0218 (9)0.0033 (8)
C14B0.0305 (9)0.0434 (11)0.0392 (10)0.0041 (8)0.0163 (8)0.0009 (8)
C15B0.0367 (10)0.0383 (10)0.0359 (10)0.0034 (8)0.0192 (8)0.0023 (8)
C16B0.0462 (12)0.0474 (12)0.0534 (12)0.0131 (9)0.0172 (10)0.0085 (9)
C17B0.0890 (19)0.0605 (15)0.100 (2)0.0013 (13)0.0514 (17)0.0230 (14)
Geometric parameters (Å, º) top
O1A—C13A1.3498 (19)O1B—C13B1.351 (2)
O1A—H1A0.82O1B—H1C0.82
O2A—C11A1.3460 (19)O2B—C11B1.3440 (19)
O2A—H2A0.82O2B—H2C0.82
O3A—C9A1.254 (2)O3B—C9B1.252 (2)
O4A—C15A1.3540 (19)O4B—C15B1.3551 (19)
O4A—C16A1.429 (2)O4B—C16B1.431 (2)
O5A—C3A1.379 (2)O5B—C3B1.375 (2)
O5A—C17A1.401 (3)O5B—C17B1.419 (3)
C1A—C6A1.371 (3)C1B—C2B1.382 (3)
C1A—C2A1.376 (3)C1B—C6B1.390 (3)
C1A—H1B0.93C1B—H1D0.93
C2A—C3A1.373 (3)C2B—C3B1.375 (3)
C2A—H2B0.93C2B—H2D0.93
C3A—C4A1.364 (3)C3B—C4B1.373 (3)
C4A—C5A1.386 (3)C4B—C5B1.382 (3)
C4A—H4A0.93C4B—H4B0.93
C5A—C6A1.368 (3)C5B—C6B1.368 (3)
C5A—H5A0.93C5B—H5B0.93
C6A—C7A1.510 (3)C6B—C7B1.518 (3)
C7A—C8A1.517 (2)C7B—C8B1.511 (2)
C7A—H7A0.97C7B—H7C0.97
C7A—H7B0.97C7B—H7D0.97
C8A—C9A1.504 (2)C8B—C9B1.506 (2)
C8A—H8A0.97C8B—H8C0.97
C8A—H8B0.97C8B—H8D0.97
C9A—C10A1.460 (2)C9B—C10B1.457 (2)
C10A—C11A1.426 (2)C10B—C15B1.425 (2)
C10A—C15A1.427 (2)C10B—C11B1.428 (2)
C11A—C12A1.381 (2)C11B—C12B1.376 (2)
C12A—C13A1.378 (2)C12B—C13B1.381 (2)
C12A—H12A0.93C12B—H12B0.93
C13A—C14A1.389 (2)C13B—C14B1.388 (2)
C14A—C15A1.373 (2)C14B—C15B1.380 (2)
C14A—H14A0.93C14B—H14B0.93
C16A—H16A0.96C16B—H16D0.96
C16A—H16B0.96C16B—H16E0.96
C16A—H16C0.96C16B—H16F0.96
C17A—H17A0.96C17B—H17D0.96
C17A—H17B0.96C17B—H17E0.96
C17A—H17C0.96C17B—H17F0.96
C13A—O1A—H1A109.5C13B—O1B—H1C109.5
C11A—O2A—H2A109.5C11B—O2B—H2C109.5
C15A—O4A—C16A119.04 (14)C15B—O4B—C16B119.18 (14)
C3A—O5A—C17A118.24 (19)C3B—O5B—C17B117.72 (18)
C6A—C1A—C2A121.4 (2)C2B—C1B—C6B121.4 (2)
C6A—C1A—H1B119.3C2B—C1B—H1D119.3
C2A—C1A—H1B119.3C6B—C1B—H1D119.3
C3A—C2A—C1A120.9 (2)C3B—C2B—C1B120.2 (2)
C3A—C2A—H2B119.5C3B—C2B—H2D119.9
C1A—C2A—H2B119.5C1B—C2B—H2D119.9
C4A—C3A—C2A118.7 (2)C4B—C3B—O5B124.7 (2)
C4A—C3A—O5A124.4 (2)C4B—C3B—C2B119.2 (2)
C2A—C3A—O5A116.9 (2)O5B—C3B—C2B116.1 (2)
C3A—C4A—C5A119.5 (2)C3B—C4B—C5B119.7 (2)
C3A—C4A—H4A120.2C3B—C4B—H4B120.2
C5A—C4A—H4A120.2C5B—C4B—H4B120.2
C6A—C5A—C4A122.5 (2)C6B—C5B—C4B122.6 (2)
C6A—C5A—H5A118.7C6B—C5B—H5B118.7
C4A—C5A—H5A118.7C4B—C5B—H5B118.7
C5A—C6A—C1A116.93 (19)C5B—C6B—C1B116.9 (2)
C5A—C6A—C7A120.98 (19)C5B—C6B—C7B120.5 (2)
C1A—C6A—C7A122.1 (2)C1B—C6B—C7B122.6 (2)
C6A—C7A—C8A111.87 (15)C8B—C7B—C6B112.50 (16)
C6A—C7A—H7A109.2C8B—C7B—H7C109.1
C8A—C7A—H7A109.2C6B—C7B—H7C109.1
C6A—C7A—H7B109.2C8B—C7B—H7D109.1
C8A—C7A—H7B109.2C6B—C7B—H7D109.1
H7A—C7A—H7B107.9H7C—C7B—H7D107.8
C9A—C8A—C7A114.40 (15)C9B—C8B—C7B114.13 (15)
C9A—C8A—H8A108.7C9B—C8B—H8C108.7
C7A—C8A—H8A108.7C7B—C8B—H8C108.7
C9A—C8A—H8B108.7C9B—C8B—H8D108.7
C7A—C8A—H8B108.7C7B—C8B—H8D108.7
H8A—C8A—H8B107.6H8C—C8B—H8D107.6
O3A—C9A—C10A119.08 (15)O3B—C9B—C10B119.43 (16)
O3A—C9A—C8A117.73 (15)O3B—C9B—C8B117.69 (15)
C10A—C9A—C8A123.17 (15)C10B—C9B—C8B122.85 (15)
C11A—C10A—C15A115.74 (15)C15B—C10B—C11B115.64 (15)
C11A—C10A—C9A119.46 (15)C15B—C10B—C9B125.05 (16)
C15A—C10A—C9A124.80 (15)C11B—C10B—C9B119.30 (15)
O2A—C11A—C12A116.08 (15)O2B—C11B—C12B116.14 (15)
O2A—C11A—C10A121.72 (15)O2B—C11B—C10B121.64 (15)
C12A—C11A—C10A122.19 (15)C12B—C11B—C10B122.21 (15)
C13A—C12A—C11A119.33 (16)C11B—C12B—C13B119.62 (16)
C13A—C12A—H12A120.3C11B—C12B—H12B120.2
C11A—C12A—H12A120.3C13B—C12B—H12B120.2
O1A—C13A—C12A116.62 (16)O1B—C13B—C12B117.14 (15)
O1A—C13A—C14A122.24 (15)O1B—C13B—C14B121.90 (15)
C12A—C13A—C14A121.13 (16)C12B—C13B—C14B120.96 (16)
C15A—C14A—C13A119.76 (16)C15B—C14B—C13B119.62 (16)
C15A—C14A—H14A120.1C15B—C14B—H14B120.2
C13A—C14A—H14A120.1C13B—C14B—H14B120.2
O4A—C15A—C14A122.22 (15)O4B—C15B—C14B121.51 (15)
O4A—C15A—C10A115.96 (15)O4B—C15B—C10B116.57 (15)
C14A—C15A—C10A121.81 (16)C14B—C15B—C10B121.92 (16)
O4A—C16A—H16A109.5O4B—C16B—H16D109.5
O4A—C16A—H16B109.5O4B—C16B—H16E109.5
H16A—C16A—H16B109.5H16D—C16B—H16E109.5
O4A—C16A—H16C109.5O4B—C16B—H16F109.5
H16A—C16A—H16C109.5H16D—C16B—H16F109.5
H16B—C16A—H16C109.5H16E—C16B—H16F109.5
O5A—C17A—H17A109.5O5B—C17B—H17D109.5
O5A—C17A—H17B109.5O5B—C17B—H17E109.5
H17A—C17A—H17B109.5H17D—C17B—H17E109.5
O5A—C17A—H17C109.5O5B—C17B—H17F109.5
H17A—C17A—H17C109.5H17D—C17B—H17F109.5
H17B—C17A—H17C109.5H17E—C17B—H17F109.5
C6A—C1A—C2A—C3A0.0 (4)C6B—C1B—C2B—C3B0.6 (4)
C1A—C2A—C3A—C4A1.0 (4)C17B—O5B—C3B—C4B6.5 (3)
C1A—C2A—C3A—O5A178.6 (2)C17B—O5B—C3B—C2B173.6 (2)
C17A—O5A—C3A—C4A9.2 (3)C1B—C2B—C3B—C4B0.2 (3)
C17A—O5A—C3A—C2A170.4 (2)C1B—C2B—C3B—O5B179.7 (2)
C2A—C3A—C4A—C5A0.9 (3)O5B—C3B—C4B—C5B179.7 (2)
O5A—C3A—C4A—C5A178.7 (2)C2B—C3B—C4B—C5B0.4 (3)
C3A—C4A—C5A—C6A0.2 (3)C3B—C4B—C5B—C6B0.7 (4)
C4A—C5A—C6A—C1A1.2 (3)C4B—C5B—C6B—C1B0.3 (3)
C4A—C5A—C6A—C7A179.51 (19)C4B—C5B—C6B—C7B179.9 (2)
C2A—C1A—C6A—C5A1.0 (4)C2B—C1B—C6B—C5B0.4 (3)
C2A—C1A—C6A—C7A179.4 (2)C2B—C1B—C6B—C7B179.2 (2)
C5A—C6A—C7A—C8A82.6 (2)C5B—C6B—C7B—C8B110.8 (2)
C1A—C6A—C7A—C8A95.7 (2)C1B—C6B—C7B—C8B68.7 (3)
C6A—C7A—C8A—C9A171.32 (16)C6B—C7B—C8B—C9B168.49 (17)
C7A—C8A—C9A—O3A7.0 (2)C7B—C8B—C9B—O3B0.7 (3)
C7A—C8A—C9A—C10A171.88 (16)C7B—C8B—C9B—C10B177.31 (17)
O3A—C9A—C10A—C11A4.9 (2)O3B—C9B—C10B—C15B176.54 (16)
C8A—C9A—C10A—C11A173.94 (16)C8B—C9B—C10B—C15B5.5 (3)
O3A—C9A—C10A—C15A175.10 (16)O3B—C9B—C10B—C11B3.8 (3)
C8A—C9A—C10A—C15A6.0 (3)C8B—C9B—C10B—C11B174.18 (16)
C15A—C10A—C11A—O2A179.44 (15)C15B—C10B—C11B—O2B179.77 (15)
C9A—C10A—C11A—O2A0.6 (2)C9B—C10B—C11B—O2B0.5 (3)
C15A—C10A—C11A—C12A1.7 (2)C15B—C10B—C11B—C12B1.4 (3)
C9A—C10A—C11A—C12A178.30 (16)C9B—C10B—C11B—C12B178.32 (16)
O2A—C11A—C12A—C13A179.60 (15)O2B—C11B—C12B—C13B179.90 (15)
C10A—C11A—C12A—C13A0.6 (3)C10B—C11B—C12B—C13B1.2 (3)
C11A—C12A—C13A—O1A179.40 (15)C11B—C12B—C13B—O1B179.85 (16)
C11A—C12A—C13A—C14A1.0 (3)C11B—C12B—C13B—C14B0.0 (3)
O1A—C13A—C14A—C15A178.89 (16)O1B—C13B—C14B—C15B179.20 (16)
C12A—C13A—C14A—C15A1.5 (3)C12B—C13B—C14B—C15B1.0 (3)
C16A—O4A—C15A—C14A6.4 (3)C16B—O4B—C15B—C14B9.6 (3)
C16A—O4A—C15A—C10A173.05 (16)C16B—O4B—C15B—C10B170.92 (16)
C13A—C14A—C15A—O4A179.80 (16)C13B—C14B—C15B—O4B178.69 (15)
C13A—C14A—C15A—C10A0.4 (3)C13B—C14B—C15B—C10B0.8 (3)
C11A—C10A—C15A—O4A178.30 (15)C11B—C10B—C15B—O4B179.86 (15)
C9A—C10A—C15A—O4A1.7 (2)C9B—C10B—C15B—O4B0.2 (3)
C11A—C10A—C15A—C14A1.1 (2)C11B—C10B—C15B—C14B0.4 (2)
C9A—C10A—C15A—C14A178.85 (16)C9B—C10B—C15B—C14B179.29 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O3Ai0.821.942.755 (2)175
O2A—H2A···O3A0.821.782.505 (2)147
O1B—H1C···O3Bi0.821.972.783 (2)173
O2B—H2C···O3B0.821.772.504 (2)147
Symmetry code: (i) x1, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC17H18O5
Mr302.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)273
a, b, c (Å)9.7048 (2), 28.9048 (5), 13.4920 (2)
β (°) 127.770 (1)
V3)2991.72 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.50 × 0.42 × 0.07
Data collection
DiffractometerBruker SMART APEX2 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.952, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
26484, 7172, 3709
Rint0.037
(sin θ/λ)max1)0.659
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.156, 1.03
No. of reflections7130
No. of parameters405
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.21

Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top
O1A—C13A1.3498 (19)O4A—C16A1.429 (2)
O2A—C11A1.3460 (19)O5A—C3A1.379 (2)
O3A—C9A1.254 (2)O5A—C17A1.401 (3)
O4A—C15A1.3540 (19)
C6A—C7A—C8A111.87 (15)C8B—C7B—C6B112.50 (16)
C9A—C8A—C7A114.40 (15)C9B—C8B—C7B114.13 (15)
O3A—C9A—C8A117.73 (15)O3B—C9B—C8B117.69 (15)
C10A—C9A—C8A123.17 (15)C10B—C9B—C8B122.85 (15)
C17A—O5A—C3A—C4A9.2 (3)C17B—O5B—C3B—C4B6.5 (3)
C6A—C7A—C8A—C9A171.32 (16)C6B—C7B—C8B—C9B168.49 (17)
C7A—C8A—C9A—C10A171.88 (16)C7B—C8B—C9B—C10B177.31 (17)
C16A—O4A—C15A—C14A6.4 (3)C16B—O4B—C15B—C14B9.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O3Ai0.821.942.755 (2)175
O2A—H2A···O3A0.821.782.505 (2)147
O1B—H1C···O3Bi0.821.972.783 (2)173
O2B—H2C···O3B0.821.772.504 (2)147
Symmetry code: (i) x1, y+1/2, z1/2.
 

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