Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028291/ci6648sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028291/ci6648Isup2.hkl |
CCDC reference: 287513
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (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
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).
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.
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).
C17H18O5 | F(000) = 1280 |
Mr = 302.31 | Dx = 1.342 Mg m−3 |
Monoclinic, P21/c | Melting point = 442–443 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7048 (2) Å | Cell parameters from 7172 reflections |
b = 28.9048 (5) Å | θ = 1.4–27.9° |
c = 13.4920 (2) Å | µ = 0.10 mm−1 |
β = 127.770 (1)° | T = 273 K |
V = 2991.72 (10) Å3 | Plate, colourless |
Z = 8 | 0.50 × 0.42 × 0.07 mm |
Bruker SMART APEX2 CCD area-detector diffractometer | 7172 independent reflections |
Radiation source: fine-focus sealed tube | 3709 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.9°, θmin = 1.4° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −38→29 |
Tmin = 0.952, Tmax = 0.993 | l = −14→17 |
26484 measured reflections |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H-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 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C17H18O5 | V = 2991.72 (10) Å3 |
Mr = 302.31 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.7048 (2) Å | µ = 0.10 mm−1 |
b = 28.9048 (5) Å | T = 273 K |
c = 13.4920 (2) Å | 0.50 × 0.42 × 0.07 mm |
β = 127.770 (1)° |
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 = 0.993 | Rint = 0.037 |
26484 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.18 e Å−3 |
7130 reflections | Δρmin = −0.21 e Å−3 |
405 parameters |
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 | ||
O1A | −0.01879 (16) | 0.32902 (4) | 0.40421 (12) | 0.0545 (4) | |
H1A | −0.1177 | 0.3183 | 0.3579 | 0.065* | |
O2A | 0.56058 (15) | 0.28692 (4) | 0.69543 (12) | 0.0514 (4) | |
H2A | 0.6257 | 0.2645 | 0.7279 | 0.062* | |
O3A | 0.64501 (15) | 0.20324 (4) | 0.73696 (11) | 0.0501 (3) | |
O4A | 0.12998 (16) | 0.16833 (4) | 0.47857 (12) | 0.0559 (4) | |
O5A | 0.4342 (3) | −0.07587 (5) | 0.76468 (18) | 0.0951 (6) | |
C1A | 0.5735 (3) | 0.02634 (8) | 0.6925 (2) | 0.0821 (8) | |
H1B | 0.6101 | 0.0333 | 0.6446 | 0.098* | |
C2A | 0.5280 (4) | −0.01844 (8) | 0.6954 (3) | 0.0941 (9) | |
H2B | 0.5344 | −0.0412 | 0.6497 | 0.113* | |
C3A | 0.4734 (3) | −0.02997 (7) | 0.7651 (2) | 0.0642 (6) | |
C4A | 0.4624 (3) | 0.00402 (7) | 0.8301 (2) | 0.0655 (6) | |
H4A | 0.4242 | −0.0029 | 0.8770 | 0.079* | |
C5A | 0.5085 (3) | 0.04893 (7) | 0.8258 (2) | 0.0632 (6) | |
H5A | 0.5000 | 0.0718 | 0.8703 | 0.076* | |
C6A | 0.5660 (2) | 0.06090 (6) | 0.75859 (19) | 0.0498 (5) | |
C7A | 0.6136 (2) | 0.11029 (6) | 0.75536 (19) | 0.0532 (5) | |
H7A | 0.6941 | 0.1106 | 0.7353 | 0.064* | |
H7B | 0.6722 | 0.1240 | 0.8377 | 0.064* | |
C8A | 0.4545 (2) | 0.13902 (6) | 0.65937 (16) | 0.0437 (4) | |
H8A | 0.4065 | 0.1277 | 0.5763 | 0.052* | |
H8B | 0.3669 | 0.1345 | 0.6717 | 0.052* | |
C9A | 0.4895 (2) | 0.19000 (6) | 0.66480 (16) | 0.0392 (4) | |
C10A | 0.3516 (2) | 0.22437 (6) | 0.59219 (15) | 0.0360 (4) | |
C11A | 0.3950 (2) | 0.27232 (6) | 0.61200 (15) | 0.0374 (4) | |
C12A | 0.2700 (2) | 0.30648 (6) | 0.54863 (16) | 0.0426 (4) | |
H12A | 0.3020 | 0.3375 | 0.5641 | 0.051* | |
C13A | 0.0975 (2) | 0.29413 (6) | 0.46230 (16) | 0.0399 (4) | |
C14A | 0.0476 (2) | 0.24795 (6) | 0.43662 (15) | 0.0403 (4) | |
H14A | −0.0690 | 0.2402 | 0.3766 | 0.048* | |
C15A | 0.1712 (2) | 0.21384 (6) | 0.50013 (15) | 0.0384 (4) | |
C16A | −0.0448 (2) | 0.15516 (6) | 0.37805 (18) | 0.0563 (5) | |
H16A | −0.0522 | 0.1221 | 0.3708 | 0.084* | |
H16B | −0.0774 | 0.1684 | 0.3011 | 0.084* | |
H16C | −0.1221 | 0.1662 | 0.3947 | 0.084* | |
C17A | 0.4040 (3) | −0.09008 (8) | 0.8492 (2) | 0.0821 (8) | |
H17A | 0.3860 | −0.1229 | 0.8427 | 0.123* | |
H17B | 0.3024 | −0.0747 | 0.8297 | 0.123* | |
H17C | 0.5030 | −0.0823 | 0.9330 | 0.123* | |
O1B | 0.46198 (16) | 0.32938 (4) | 0.39931 (13) | 0.0542 (4) | |
H1C | 0.3629 | 0.3189 | 0.3513 | 0.065* | |
O2B | 1.04122 (15) | 0.28501 (4) | 0.68117 (12) | 0.0524 (4) | |
H2C | 1.1053 | 0.2623 | 0.7111 | 0.063* | |
O3B | 1.12152 (15) | 0.20107 (4) | 0.72066 (12) | 0.0530 (4) | |
O4B | 0.60078 (16) | 0.16824 (4) | 0.47141 (12) | 0.0565 (4) | |
O5B | 0.9202 (2) | −0.07618 (5) | 0.76733 (16) | 0.0797 (5) | |
C1B | 0.9623 (3) | 0.02773 (8) | 0.6389 (2) | 0.0739 (7) | |
H1D | 0.9337 | 0.0371 | 0.5624 | 0.089* | |
C2B | 0.9220 (3) | −0.01670 (8) | 0.6512 (2) | 0.0748 (7) | |
H2D | 0.8659 | −0.0368 | 0.5830 | 0.090* | |
C3B | 0.9646 (3) | −0.03136 (7) | 0.7639 (2) | 0.0606 (6) | |
C4B | 1.0469 (3) | −0.00131 (7) | 0.8635 (2) | 0.0689 (6) | |
H4B | 1.0771 | −0.0108 | 0.9404 | 0.083* | |
C5B | 1.0845 (3) | 0.04314 (7) | 0.8490 (2) | 0.0687 (6) | |
H5B | 1.1392 | 0.0632 | 0.9171 | 0.082* | |
C6B | 1.0446 (3) | 0.05875 (7) | 0.7384 (2) | 0.0584 (6) | |
C7B | 1.0884 (3) | 0.10794 (7) | 0.7272 (2) | 0.0663 (6) | |
H7C | 1.1627 | 0.1218 | 0.8100 | 0.080* | |
H7D | 1.1530 | 0.1073 | 0.6939 | 0.080* | |
C8B | 0.9278 (2) | 0.13759 (6) | 0.64330 (17) | 0.0472 (5) | |
H8C | 0.8657 | 0.1272 | 0.5574 | 0.057* | |
H8D | 0.8517 | 0.1330 | 0.6663 | 0.057* | |
C9B | 0.9654 (2) | 0.18851 (6) | 0.64964 (16) | 0.0405 (4) | |
C10B | 0.8286 (2) | 0.22322 (6) | 0.58025 (15) | 0.0381 (4) | |
C11B | 0.8745 (2) | 0.27111 (6) | 0.60042 (16) | 0.0393 (4) | |
C12B | 0.7514 (2) | 0.30562 (6) | 0.54034 (16) | 0.0431 (4) | |
H12B | 0.7853 | 0.3365 | 0.5566 | 0.052* | |
C13B | 0.5772 (2) | 0.29413 (6) | 0.45578 (16) | 0.0402 (4) | |
C14B | 0.5243 (2) | 0.24821 (6) | 0.43030 (16) | 0.0410 (4) | |
H14B | 0.4068 | 0.2409 | 0.3722 | 0.049* | |
C15B | 0.6472 (2) | 0.21347 (6) | 0.49171 (15) | 0.0389 (4) | |
C16B | 0.4246 (2) | 0.15593 (7) | 0.37094 (18) | 0.0577 (6) | |
H16D | 0.4142 | 0.1229 | 0.3640 | 0.087* | |
H16E | 0.3932 | 0.1687 | 0.2939 | 0.087* | |
H16F | 0.3484 | 0.1680 | 0.3875 | 0.087* | |
C17B | 0.9454 (3) | −0.09108 (8) | 0.8776 (2) | 0.0872 (8) | |
H17D | 0.9142 | −0.1231 | 0.8695 | 0.131* | |
H17E | 0.8734 | −0.0730 | 0.8894 | 0.131* | |
H17F | 1.0655 | −0.0871 | 0.9485 | 0.131* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0351 (7) | 0.0413 (7) | 0.0646 (9) | 0.0027 (6) | 0.0190 (7) | 0.0049 (6) |
O2A | 0.0296 (7) | 0.0460 (7) | 0.0557 (8) | −0.0054 (6) | 0.0144 (6) | 0.0009 (6) |
O3A | 0.0291 (7) | 0.0488 (8) | 0.0528 (8) | 0.0000 (6) | 0.0152 (6) | 0.0053 (6) |
O4A | 0.0367 (7) | 0.0380 (7) | 0.0549 (8) | −0.0037 (6) | 0.0086 (6) | −0.0017 (6) |
O5A | 0.1403 (17) | 0.0407 (9) | 0.1297 (16) | −0.0085 (9) | 0.0957 (15) | −0.0057 (9) |
C1A | 0.120 (2) | 0.0539 (15) | 0.114 (2) | 0.0141 (14) | 0.093 (2) | 0.0099 (14) |
C2A | 0.157 (3) | 0.0472 (15) | 0.127 (2) | 0.0068 (15) | 0.112 (2) | −0.0068 (15) |
C3A | 0.0737 (16) | 0.0384 (12) | 0.0804 (16) | 0.0009 (10) | 0.0473 (14) | 0.0003 (11) |
C4A | 0.0778 (16) | 0.0529 (13) | 0.0786 (16) | −0.0036 (11) | 0.0544 (14) | 0.0001 (12) |
C5A | 0.0782 (16) | 0.0425 (12) | 0.0744 (15) | −0.0034 (11) | 0.0496 (14) | −0.0046 (11) |
C6A | 0.0374 (10) | 0.0429 (11) | 0.0575 (13) | 0.0074 (8) | 0.0232 (10) | 0.0083 (10) |
C7A | 0.0405 (11) | 0.0452 (11) | 0.0650 (13) | 0.0037 (9) | 0.0277 (10) | 0.0076 (10) |
C8A | 0.0375 (10) | 0.0427 (10) | 0.0449 (11) | 0.0013 (8) | 0.0222 (9) | 0.0043 (8) |
C9A | 0.0343 (10) | 0.0453 (11) | 0.0353 (10) | −0.0003 (8) | 0.0200 (8) | 0.0019 (8) |
C10A | 0.0309 (9) | 0.0381 (10) | 0.0342 (9) | 0.0000 (7) | 0.0175 (8) | 0.0019 (8) |
C11A | 0.0296 (9) | 0.0422 (10) | 0.0352 (9) | −0.0053 (8) | 0.0172 (8) | −0.0008 (8) |
C12A | 0.0378 (10) | 0.0369 (10) | 0.0458 (11) | −0.0038 (8) | 0.0218 (9) | 0.0002 (8) |
C13A | 0.0346 (10) | 0.0416 (11) | 0.0391 (10) | 0.0035 (8) | 0.0204 (8) | 0.0045 (8) |
C14A | 0.0292 (9) | 0.0416 (10) | 0.0363 (10) | −0.0027 (8) | 0.0130 (8) | −0.0011 (8) |
C15A | 0.0350 (10) | 0.0370 (10) | 0.0352 (10) | −0.0030 (8) | 0.0175 (8) | −0.0008 (8) |
C16A | 0.0414 (11) | 0.0478 (11) | 0.0509 (12) | −0.0117 (9) | 0.0136 (10) | −0.0068 (9) |
C17A | 0.0711 (16) | 0.0570 (15) | 0.108 (2) | −0.0067 (12) | 0.0495 (16) | 0.0123 (14) |
O1B | 0.0378 (7) | 0.0408 (7) | 0.0642 (9) | 0.0027 (6) | 0.0211 (7) | 0.0042 (6) |
O2B | 0.0312 (7) | 0.0487 (8) | 0.0556 (8) | −0.0063 (6) | 0.0156 (6) | 0.0010 (7) |
O3B | 0.0331 (7) | 0.0511 (8) | 0.0589 (8) | 0.0007 (6) | 0.0200 (7) | 0.0074 (6) |
O4B | 0.0378 (7) | 0.0374 (7) | 0.0602 (9) | −0.0054 (6) | 0.0126 (7) | −0.0030 (6) |
O5B | 0.0965 (13) | 0.0417 (9) | 0.1014 (13) | −0.0068 (8) | 0.0608 (11) | −0.0011 (8) |
C1B | 0.0860 (18) | 0.0628 (15) | 0.0738 (16) | 0.0037 (13) | 0.0494 (15) | 0.0118 (13) |
C2B | 0.0896 (18) | 0.0537 (14) | 0.0756 (17) | −0.0033 (13) | 0.0478 (15) | −0.0064 (12) |
C3B | 0.0581 (13) | 0.0404 (12) | 0.0808 (16) | 0.0031 (10) | 0.0414 (13) | 0.0041 (11) |
C4B | 0.0762 (16) | 0.0519 (13) | 0.0712 (15) | −0.0059 (12) | 0.0413 (14) | 0.0055 (12) |
C5B | 0.0685 (15) | 0.0487 (13) | 0.0740 (16) | −0.0065 (11) | 0.0360 (13) | −0.0003 (12) |
C6B | 0.0466 (12) | 0.0454 (12) | 0.0751 (15) | 0.0059 (9) | 0.0331 (12) | 0.0099 (11) |
C7B | 0.0465 (12) | 0.0483 (12) | 0.0934 (17) | 0.0050 (10) | 0.0373 (12) | 0.0170 (11) |
C8B | 0.0390 (10) | 0.0448 (11) | 0.0542 (12) | 0.0007 (8) | 0.0266 (10) | 0.0061 (9) |
C9B | 0.0350 (10) | 0.0474 (11) | 0.0378 (10) | −0.0008 (8) | 0.0216 (8) | 0.0031 (8) |
C10B | 0.0325 (9) | 0.0404 (10) | 0.0363 (10) | −0.0009 (8) | 0.0185 (8) | 0.0007 (8) |
C11B | 0.0329 (9) | 0.0425 (10) | 0.0373 (10) | −0.0064 (8) | 0.0188 (8) | −0.0013 (8) |
C12B | 0.0402 (10) | 0.0370 (10) | 0.0443 (11) | −0.0044 (8) | 0.0219 (9) | 0.0000 (8) |
C13B | 0.0379 (10) | 0.0399 (10) | 0.0392 (10) | 0.0017 (8) | 0.0218 (9) | 0.0033 (8) |
C14B | 0.0305 (9) | 0.0434 (11) | 0.0392 (10) | −0.0041 (8) | 0.0163 (8) | −0.0009 (8) |
C15B | 0.0367 (10) | 0.0383 (10) | 0.0359 (10) | −0.0034 (8) | 0.0192 (8) | −0.0023 (8) |
C16B | 0.0462 (12) | 0.0474 (12) | 0.0534 (12) | −0.0131 (9) | 0.0172 (10) | −0.0085 (9) |
C17B | 0.0890 (19) | 0.0605 (15) | 0.100 (2) | −0.0013 (13) | 0.0514 (17) | 0.0230 (14) |
O1A—C13A | 1.3498 (19) | O1B—C13B | 1.351 (2) |
O1A—H1A | 0.82 | O1B—H1C | 0.82 |
O2A—C11A | 1.3460 (19) | O2B—C11B | 1.3440 (19) |
O2A—H2A | 0.82 | O2B—H2C | 0.82 |
O3A—C9A | 1.254 (2) | O3B—C9B | 1.252 (2) |
O4A—C15A | 1.3540 (19) | O4B—C15B | 1.3551 (19) |
O4A—C16A | 1.429 (2) | O4B—C16B | 1.431 (2) |
O5A—C3A | 1.379 (2) | O5B—C3B | 1.375 (2) |
O5A—C17A | 1.401 (3) | O5B—C17B | 1.419 (3) |
C1A—C6A | 1.371 (3) | C1B—C2B | 1.382 (3) |
C1A—C2A | 1.376 (3) | C1B—C6B | 1.390 (3) |
C1A—H1B | 0.93 | C1B—H1D | 0.93 |
C2A—C3A | 1.373 (3) | C2B—C3B | 1.375 (3) |
C2A—H2B | 0.93 | C2B—H2D | 0.93 |
C3A—C4A | 1.364 (3) | C3B—C4B | 1.373 (3) |
C4A—C5A | 1.386 (3) | C4B—C5B | 1.382 (3) |
C4A—H4A | 0.93 | C4B—H4B | 0.93 |
C5A—C6A | 1.368 (3) | C5B—C6B | 1.368 (3) |
C5A—H5A | 0.93 | C5B—H5B | 0.93 |
C6A—C7A | 1.510 (3) | C6B—C7B | 1.518 (3) |
C7A—C8A | 1.517 (2) | C7B—C8B | 1.511 (2) |
C7A—H7A | 0.97 | C7B—H7C | 0.97 |
C7A—H7B | 0.97 | C7B—H7D | 0.97 |
C8A—C9A | 1.504 (2) | C8B—C9B | 1.506 (2) |
C8A—H8A | 0.97 | C8B—H8C | 0.97 |
C8A—H8B | 0.97 | C8B—H8D | 0.97 |
C9A—C10A | 1.460 (2) | C9B—C10B | 1.457 (2) |
C10A—C11A | 1.426 (2) | C10B—C15B | 1.425 (2) |
C10A—C15A | 1.427 (2) | C10B—C11B | 1.428 (2) |
C11A—C12A | 1.381 (2) | C11B—C12B | 1.376 (2) |
C12A—C13A | 1.378 (2) | C12B—C13B | 1.381 (2) |
C12A—H12A | 0.93 | C12B—H12B | 0.93 |
C13A—C14A | 1.389 (2) | C13B—C14B | 1.388 (2) |
C14A—C15A | 1.373 (2) | C14B—C15B | 1.380 (2) |
C14A—H14A | 0.93 | C14B—H14B | 0.93 |
C16A—H16A | 0.96 | C16B—H16D | 0.96 |
C16A—H16B | 0.96 | C16B—H16E | 0.96 |
C16A—H16C | 0.96 | C16B—H16F | 0.96 |
C17A—H17A | 0.96 | C17B—H17D | 0.96 |
C17A—H17B | 0.96 | C17B—H17E | 0.96 |
C17A—H17C | 0.96 | C17B—H17F | 0.96 |
C13A—O1A—H1A | 109.5 | C13B—O1B—H1C | 109.5 |
C11A—O2A—H2A | 109.5 | C11B—O2B—H2C | 109.5 |
C15A—O4A—C16A | 119.04 (14) | C15B—O4B—C16B | 119.18 (14) |
C3A—O5A—C17A | 118.24 (19) | C3B—O5B—C17B | 117.72 (18) |
C6A—C1A—C2A | 121.4 (2) | C2B—C1B—C6B | 121.4 (2) |
C6A—C1A—H1B | 119.3 | C2B—C1B—H1D | 119.3 |
C2A—C1A—H1B | 119.3 | C6B—C1B—H1D | 119.3 |
C3A—C2A—C1A | 120.9 (2) | C3B—C2B—C1B | 120.2 (2) |
C3A—C2A—H2B | 119.5 | C3B—C2B—H2D | 119.9 |
C1A—C2A—H2B | 119.5 | C1B—C2B—H2D | 119.9 |
C4A—C3A—C2A | 118.7 (2) | C4B—C3B—O5B | 124.7 (2) |
C4A—C3A—O5A | 124.4 (2) | C4B—C3B—C2B | 119.2 (2) |
C2A—C3A—O5A | 116.9 (2) | O5B—C3B—C2B | 116.1 (2) |
C3A—C4A—C5A | 119.5 (2) | C3B—C4B—C5B | 119.7 (2) |
C3A—C4A—H4A | 120.2 | C3B—C4B—H4B | 120.2 |
C5A—C4A—H4A | 120.2 | C5B—C4B—H4B | 120.2 |
C6A—C5A—C4A | 122.5 (2) | C6B—C5B—C4B | 122.6 (2) |
C6A—C5A—H5A | 118.7 | C6B—C5B—H5B | 118.7 |
C4A—C5A—H5A | 118.7 | C4B—C5B—H5B | 118.7 |
C5A—C6A—C1A | 116.93 (19) | C5B—C6B—C1B | 116.9 (2) |
C5A—C6A—C7A | 120.98 (19) | C5B—C6B—C7B | 120.5 (2) |
C1A—C6A—C7A | 122.1 (2) | C1B—C6B—C7B | 122.6 (2) |
C6A—C7A—C8A | 111.87 (15) | C8B—C7B—C6B | 112.50 (16) |
C6A—C7A—H7A | 109.2 | C8B—C7B—H7C | 109.1 |
C8A—C7A—H7A | 109.2 | C6B—C7B—H7C | 109.1 |
C6A—C7A—H7B | 109.2 | C8B—C7B—H7D | 109.1 |
C8A—C7A—H7B | 109.2 | C6B—C7B—H7D | 109.1 |
H7A—C7A—H7B | 107.9 | H7C—C7B—H7D | 107.8 |
C9A—C8A—C7A | 114.40 (15) | C9B—C8B—C7B | 114.13 (15) |
C9A—C8A—H8A | 108.7 | C9B—C8B—H8C | 108.7 |
C7A—C8A—H8A | 108.7 | C7B—C8B—H8C | 108.7 |
C9A—C8A—H8B | 108.7 | C9B—C8B—H8D | 108.7 |
C7A—C8A—H8B | 108.7 | C7B—C8B—H8D | 108.7 |
H8A—C8A—H8B | 107.6 | H8C—C8B—H8D | 107.6 |
O3A—C9A—C10A | 119.08 (15) | O3B—C9B—C10B | 119.43 (16) |
O3A—C9A—C8A | 117.73 (15) | O3B—C9B—C8B | 117.69 (15) |
C10A—C9A—C8A | 123.17 (15) | C10B—C9B—C8B | 122.85 (15) |
C11A—C10A—C15A | 115.74 (15) | C15B—C10B—C11B | 115.64 (15) |
C11A—C10A—C9A | 119.46 (15) | C15B—C10B—C9B | 125.05 (16) |
C15A—C10A—C9A | 124.80 (15) | C11B—C10B—C9B | 119.30 (15) |
O2A—C11A—C12A | 116.08 (15) | O2B—C11B—C12B | 116.14 (15) |
O2A—C11A—C10A | 121.72 (15) | O2B—C11B—C10B | 121.64 (15) |
C12A—C11A—C10A | 122.19 (15) | C12B—C11B—C10B | 122.21 (15) |
C13A—C12A—C11A | 119.33 (16) | C11B—C12B—C13B | 119.62 (16) |
C13A—C12A—H12A | 120.3 | C11B—C12B—H12B | 120.2 |
C11A—C12A—H12A | 120.3 | C13B—C12B—H12B | 120.2 |
O1A—C13A—C12A | 116.62 (16) | O1B—C13B—C12B | 117.14 (15) |
O1A—C13A—C14A | 122.24 (15) | O1B—C13B—C14B | 121.90 (15) |
C12A—C13A—C14A | 121.13 (16) | C12B—C13B—C14B | 120.96 (16) |
C15A—C14A—C13A | 119.76 (16) | C15B—C14B—C13B | 119.62 (16) |
C15A—C14A—H14A | 120.1 | C15B—C14B—H14B | 120.2 |
C13A—C14A—H14A | 120.1 | C13B—C14B—H14B | 120.2 |
O4A—C15A—C14A | 122.22 (15) | O4B—C15B—C14B | 121.51 (15) |
O4A—C15A—C10A | 115.96 (15) | O4B—C15B—C10B | 116.57 (15) |
C14A—C15A—C10A | 121.81 (16) | C14B—C15B—C10B | 121.92 (16) |
O4A—C16A—H16A | 109.5 | O4B—C16B—H16D | 109.5 |
O4A—C16A—H16B | 109.5 | O4B—C16B—H16E | 109.5 |
H16A—C16A—H16B | 109.5 | H16D—C16B—H16E | 109.5 |
O4A—C16A—H16C | 109.5 | O4B—C16B—H16F | 109.5 |
H16A—C16A—H16C | 109.5 | H16D—C16B—H16F | 109.5 |
H16B—C16A—H16C | 109.5 | H16E—C16B—H16F | 109.5 |
O5A—C17A—H17A | 109.5 | O5B—C17B—H17D | 109.5 |
O5A—C17A—H17B | 109.5 | O5B—C17B—H17E | 109.5 |
H17A—C17A—H17B | 109.5 | H17D—C17B—H17E | 109.5 |
O5A—C17A—H17C | 109.5 | O5B—C17B—H17F | 109.5 |
H17A—C17A—H17C | 109.5 | H17D—C17B—H17F | 109.5 |
H17B—C17A—H17C | 109.5 | H17E—C17B—H17F | 109.5 |
C6A—C1A—C2A—C3A | 0.0 (4) | C6B—C1B—C2B—C3B | −0.6 (4) |
C1A—C2A—C3A—C4A | 1.0 (4) | C17B—O5B—C3B—C4B | 6.5 (3) |
C1A—C2A—C3A—O5A | −178.6 (2) | C17B—O5B—C3B—C2B | −173.6 (2) |
C17A—O5A—C3A—C4A | −9.2 (3) | C1B—C2B—C3B—C4B | 0.2 (3) |
C17A—O5A—C3A—C2A | 170.4 (2) | C1B—C2B—C3B—O5B | −179.7 (2) |
C2A—C3A—C4A—C5A | −0.9 (3) | O5B—C3B—C4B—C5B | −179.7 (2) |
O5A—C3A—C4A—C5A | 178.7 (2) | C2B—C3B—C4B—C5B | 0.4 (3) |
C3A—C4A—C5A—C6A | −0.2 (3) | C3B—C4B—C5B—C6B | −0.7 (4) |
C4A—C5A—C6A—C1A | 1.2 (3) | C4B—C5B—C6B—C1B | 0.3 (3) |
C4A—C5A—C6A—C7A | 179.51 (19) | C4B—C5B—C6B—C7B | 179.9 (2) |
C2A—C1A—C6A—C5A | −1.0 (4) | C2B—C1B—C6B—C5B | 0.4 (3) |
C2A—C1A—C6A—C7A | −179.4 (2) | C2B—C1B—C6B—C7B | −179.2 (2) |
C5A—C6A—C7A—C8A | −82.6 (2) | C5B—C6B—C7B—C8B | −110.8 (2) |
C1A—C6A—C7A—C8A | 95.7 (2) | C1B—C6B—C7B—C8B | 68.7 (3) |
C6A—C7A—C8A—C9A | 171.32 (16) | C6B—C7B—C8B—C9B | 168.49 (17) |
C7A—C8A—C9A—O3A | 7.0 (2) | C7B—C8B—C9B—O3B | 0.7 (3) |
C7A—C8A—C9A—C10A | −171.88 (16) | C7B—C8B—C9B—C10B | −177.31 (17) |
O3A—C9A—C10A—C11A | −4.9 (2) | O3B—C9B—C10B—C15B | 176.54 (16) |
C8A—C9A—C10A—C11A | 173.94 (16) | C8B—C9B—C10B—C15B | −5.5 (3) |
O3A—C9A—C10A—C15A | 175.10 (16) | O3B—C9B—C10B—C11B | −3.8 (3) |
C8A—C9A—C10A—C15A | −6.0 (3) | C8B—C9B—C10B—C11B | 174.18 (16) |
C15A—C10A—C11A—O2A | −179.44 (15) | C15B—C10B—C11B—O2B | −179.77 (15) |
C9A—C10A—C11A—O2A | 0.6 (2) | C9B—C10B—C11B—O2B | 0.5 (3) |
C15A—C10A—C11A—C12A | 1.7 (2) | C15B—C10B—C11B—C12B | 1.4 (3) |
C9A—C10A—C11A—C12A | −178.30 (16) | C9B—C10B—C11B—C12B | −178.32 (16) |
O2A—C11A—C12A—C13A | −179.60 (15) | O2B—C11B—C12B—C13B | 179.90 (15) |
C10A—C11A—C12A—C13A | −0.6 (3) | C10B—C11B—C12B—C13B | −1.2 (3) |
C11A—C12A—C13A—O1A | 179.40 (15) | C11B—C12B—C13B—O1B | −179.85 (16) |
C11A—C12A—C13A—C14A | −1.0 (3) | C11B—C12B—C13B—C14B | 0.0 (3) |
O1A—C13A—C14A—C15A | −178.89 (16) | O1B—C13B—C14B—C15B | −179.20 (16) |
C12A—C13A—C14A—C15A | 1.5 (3) | C12B—C13B—C14B—C15B | 1.0 (3) |
C16A—O4A—C15A—C14A | 6.4 (3) | C16B—O4B—C15B—C14B | 9.6 (3) |
C16A—O4A—C15A—C10A | −173.05 (16) | C16B—O4B—C15B—C10B | −170.92 (16) |
C13A—C14A—C15A—O4A | −179.80 (16) | C13B—C14B—C15B—O4B | 178.69 (15) |
C13A—C14A—C15A—C10A | −0.4 (3) | C13B—C14B—C15B—C10B | −0.8 (3) |
C11A—C10A—C15A—O4A | 178.30 (15) | C11B—C10B—C15B—O4B | −179.86 (15) |
C9A—C10A—C15A—O4A | −1.7 (2) | C9B—C10B—C15B—O4B | −0.2 (3) |
C11A—C10A—C15A—C14A | −1.1 (2) | C11B—C10B—C15B—C14B | −0.4 (2) |
C9A—C10A—C15A—C14A | 178.85 (16) | C9B—C10B—C15B—C14B | 179.29 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O3Ai | 0.82 | 1.94 | 2.755 (2) | 175 |
O2A—H2A···O3A | 0.82 | 1.78 | 2.505 (2) | 147 |
O1B—H1C···O3Bi | 0.82 | 1.97 | 2.783 (2) | 173 |
O2B—H2C···O3B | 0.82 | 1.77 | 2.504 (2) | 147 |
Symmetry code: (i) x−1, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H18O5 |
Mr | 302.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 9.7048 (2), 28.9048 (5), 13.4920 (2) |
β (°) | 127.770 (1) |
V (Å3) | 2991.72 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.50 × 0.42 × 0.07 |
Data collection | |
Diffractometer | Bruker SMART APEX2 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.952, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26484, 7172, 3709 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.659 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.156, 1.03 |
No. of reflections | 7130 |
No. of parameters | 405 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.21 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).
O1A—C13A | 1.3498 (19) | O4A—C16A | 1.429 (2) |
O2A—C11A | 1.3460 (19) | O5A—C3A | 1.379 (2) |
O3A—C9A | 1.254 (2) | O5A—C17A | 1.401 (3) |
O4A—C15A | 1.3540 (19) | ||
C6A—C7A—C8A | 111.87 (15) | C8B—C7B—C6B | 112.50 (16) |
C9A—C8A—C7A | 114.40 (15) | C9B—C8B—C7B | 114.13 (15) |
O3A—C9A—C8A | 117.73 (15) | O3B—C9B—C8B | 117.69 (15) |
C10A—C9A—C8A | 123.17 (15) | C10B—C9B—C8B | 122.85 (15) |
C17A—O5A—C3A—C4A | −9.2 (3) | C17B—O5B—C3B—C4B | 6.5 (3) |
C6A—C7A—C8A—C9A | 171.32 (16) | C6B—C7B—C8B—C9B | 168.49 (17) |
C7A—C8A—C9A—C10A | −171.88 (16) | C7B—C8B—C9B—C10B | −177.31 (17) |
C16A—O4A—C15A—C14A | 6.4 (3) | C16B—O4B—C15B—C14B | 9.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O3Ai | 0.82 | 1.94 | 2.755 (2) | 175 |
O2A—H2A···O3A | 0.82 | 1.78 | 2.505 (2) | 147 |
O1B—H1C···O3Bi | 0.82 | 1.97 | 2.783 (2) | 173 |
O2B—H2C···O3B | 0.82 | 1.77 | 2.504 (2) | 147 |
Symmetry code: (i) x−1, −y+1/2, z−1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
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—C9═O3 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—C9═O3 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).