Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050234/hg2310sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050234/hg2310Isup2.hkl |
CCDC reference: 667382
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.032
- wR factor = 0.083
- Data-to-parameter ratio = 9.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.27 Ratio
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.38 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.63 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.62 From the CIF: _reflns_number_total 1915 Count of symmetry unique reflns 1927 Completeness (_total/calc) 99.38% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT792_ALERT_1_G Check the Absolute Configuration of C11 = ... S PLAT792_ALERT_1_G Check the Absolute Configuration of C12 = ... S PLAT792_ALERT_1_G Check the Absolute Configuration of C13 = ... R PLAT792_ALERT_1_G Check the Absolute Configuration of C14 = ... R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared according to literature method (Wei, 2004). Single crystals suitable for X-ray determination were obtained by slow evaporation of a AcOEt solution over a period of several days. IR (film): 3361, 2934, 2837, 1730, 1601, 1587, 1490, 1257, 1155, 1038 cm-1; 1H NMR (200 MHz, CDCl3) delta 2.14–2.47 (m, 2H), 2.67–2.90 (m, 2H), 3.25–3.40 (m, 2H), 3.61–3.79 (m, 2H), 3.78 (m, 2H), 3.81 (s, 3H), 4.86 (d, J = 4.4 Hz, 1H), 6.15 (d, J = 5.8 Hz, 1H), 6.29 (dd, J = 3.8, 5.8 Hz, 1H), 6.75–6.85 (m, 3H), 7.19 (dd, J = 7.4, 7.6 Hz, 1H) p.p.m.; 13C NMR (75 MHz, CDCl3) delta 31.0, 33.8, 46.9, 48.5, 55.1, 60.7, 61.0, 79.2, 90.5, 111.2, 114.0, 120.6, 129.3, 135.2, 136.6, 143.5, 159.6 p.p.m.; LRMS (EI) m/z 290 (M+, 0.04%), 272 (0.1), 254 (0.1), 202 (22), 121 (42), 81 (100).
All H atoms were placed geometrically (C—H values were set to 0.98, 0.97, 0.96, 0.93 and 0.82 A° for atoms CH, CH2, CH3, CH (phenyl) and OH, respectively) and refined with a riding model, with Uiso(H) = 1.2 or 1.5 times Ueq(C), or 1.5 Ueq(O). In the absence of significant anomalous dispersion effects, 1530 Freidel pairs were merged before refinement.
Furans are generally much less reactive dienes in Diels-Alder cycloaddition reaction due to their inherent aromaticity (Balaban et al., 2004) and usually facile retro- Diels-Alder reaction of the resulting adducts (Woodward, 1940). In view of the importance and great potential of Diels-Alder cycloadducts of furano derivatives as key intermediates for synthesizing structurally complex targets (Hudlicky et al., 1996) or achieving highly region-stereocontrolled reactions via the corresponding oxabicyclic adducts (Chiu & Lautens, 1997), a great deal of effort has been devoted to the development of chemical and physical means to promote the frequently difficult [4 + 2] cycloaddition of cyclic furano dienes. For example, Ultrasonic irradiation effectively promoted the Diels-Alder reaction of substituted furans with dimethyl maleate in very high exo selectivity (Wei, 2004) and the resulting product stereochemistry was unambiguously confirmed a single-crystal X-ray diffraction analysis (Fig. 1) of the corresponding reduction derivative diol (I). The oxidol bridge is on the same side as two hydroxymethyls, which are not parallel each other.
The molecules are linked by O···O hydrogen bonds to form a two-dimensional supramolecular network structure (Fig. 2). Inter-molecular O—H···O hydrogen bonding is observed between the O(3) and O(2) hydroxyl groups.
For related literature, see: Balaban et al. (2004); Chiu & Lautens (1997); Hudlicky et al. (1996); Wei (2004); Woodward (1940); Buser & Vasella (2005).
Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXL97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
C17H22O4 | F(000) = 624 |
Mr = 290.35 | Dx = 1.245 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 3969 reflections |
a = 11.8025 (4) Å | θ = 2.7–26.5° |
b = 14.9842 (4) Å | µ = 0.09 mm−1 |
c = 8.7569 (3) Å | T = 294 K |
V = 1548.67 (9) Å3 | Block, colorless |
Z = 4 | 0.43 × 0.27 × 0.24 mm |
Bruker APEX CCD area-detector diffractometer | 1719 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 27.6°, θmin = 2.2° |
φ and ω scans | h = −15→12 |
9219 measured reflections | k = −19→19 |
1915 independent reflections | l = −11→11 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0473P)2 + 0.1224P] where P = (Fo2 + 2Fc2)/3 |
1915 reflections | (Δ/σ)max < 0.001 |
193 parameters | Δρmax = 0.15 e Å−3 |
1 restraint | Δρmin = −0.16 e Å−3 |
C17H22O4 | V = 1548.67 (9) Å3 |
Mr = 290.35 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 11.8025 (4) Å | µ = 0.09 mm−1 |
b = 14.9842 (4) Å | T = 294 K |
c = 8.7569 (3) Å | 0.43 × 0.27 × 0.24 mm |
Bruker APEX CCD area-detector diffractometer | 1719 reflections with I > 2σ(I) |
9219 measured reflections | Rint = 0.019 |
1915 independent reflections |
R[F2 > 2σ(F2)] = 0.032 | 1 restraint |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.15 e Å−3 |
1915 reflections | Δρmin = −0.16 e Å−3 |
193 parameters |
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 | ||
O1 | 1.09490 (11) | 0.61849 (8) | 0.76469 (15) | 0.0394 (3) | |
C16 | 1.06391 (15) | 0.44022 (12) | 0.5973 (2) | 0.0395 (4) | |
H16A | 1.0072 | 0.4506 | 0.6755 | 0.047* | |
H16B | 1.0262 | 0.4142 | 0.5095 | 0.047* | |
C2 | 0.93740 (19) | 0.87373 (13) | 0.8725 (3) | 0.0521 (5) | |
C12 | 1.02937 (13) | 0.60627 (11) | 0.5159 (2) | 0.0345 (4) | |
H12 | 1.0448 | 0.6306 | 0.4141 | 0.041* | |
C17 | 0.90595 (14) | 0.57645 (12) | 0.5238 (2) | 0.0399 (4) | |
H17A | 0.8970 | 0.5218 | 0.4658 | 0.048* | |
H17B | 0.8865 | 0.5637 | 0.6292 | 0.048* | |
C9 | 0.97705 (16) | 0.74553 (13) | 0.6911 (3) | 0.0469 (5) | |
H9A | 0.9098 | 0.7149 | 0.7271 | 0.056* | |
H9B | 0.9555 | 0.7822 | 0.6046 | 0.056* | |
C11 | 1.06362 (15) | 0.67730 (11) | 0.6400 (2) | 0.0371 (4) | |
C15 | 1.25209 (18) | 0.64819 (12) | 0.6179 (3) | 0.0510 (5) | |
H15 | 1.3298 | 0.6493 | 0.6004 | 0.061* | |
C14 | 1.18359 (14) | 0.57231 (12) | 0.6848 (2) | 0.0396 (4) | |
H14 | 1.2271 | 0.5301 | 0.7471 | 0.047* | |
C1 | 0.9513 (2) | 0.96320 (13) | 0.8366 (3) | 0.0540 (5) | |
H1 | 1.0123 | 0.9811 | 0.7767 | 0.065* | |
C10 | 1.17892 (15) | 0.71219 (13) | 0.5895 (3) | 0.0482 (5) | |
H10 | 1.1945 | 0.7678 | 0.5471 | 0.058* | |
C13 | 1.11664 (13) | 0.52951 (11) | 0.5509 (2) | 0.0347 (4) | |
H13 | 1.1669 | 0.5209 | 0.4631 | 0.042* | |
O4 | 0.8824 (2) | 1.11539 (11) | 0.8606 (3) | 0.1037 (8) | |
C8 | 1.0225 (2) | 0.80543 (15) | 0.8182 (4) | 0.0675 (7) | |
H8A | 1.0449 | 0.7685 | 0.9039 | 0.081* | |
H8B | 1.0895 | 0.8362 | 0.7815 | 0.081* | |
C6 | 0.8749 (2) | 1.02585 (14) | 0.8895 (3) | 0.0633 (6) | |
C5 | 0.7847 (2) | 1.00053 (18) | 0.9786 (4) | 0.0775 (8) | |
H5 | 0.7338 | 1.0429 | 1.0148 | 0.093* | |
C3 | 0.8458 (2) | 0.84890 (16) | 0.9595 (4) | 0.0721 (7) | |
H3 | 0.8343 | 0.7890 | 0.9824 | 0.087* | |
C4 | 0.7704 (3) | 0.91245 (18) | 1.0134 (4) | 0.0867 (9) | |
H4 | 0.7096 | 0.8949 | 1.0738 | 0.104* | |
C7 | 0.9686 (4) | 1.1454 (2) | 0.7638 (5) | 0.1168 (15) | |
H7A | 1.0408 | 1.1281 | 0.8046 | 0.175* | |
H7B | 0.9652 | 1.2092 | 0.7559 | 0.175* | |
H7C | 0.9590 | 1.1195 | 0.6644 | 0.175* | |
O3 | 1.14629 (12) | 0.37876 (8) | 0.65379 (16) | 0.0444 (3) | |
H3A | 1.1970 | 0.3728 | 0.5906 | 0.067* | |
O2 | 0.82975 (11) | 0.64249 (10) | 0.46535 (16) | 0.0453 (3) | |
H2 | 0.8367 | 0.6457 | 0.3723 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0426 (6) | 0.0421 (6) | 0.0334 (6) | 0.0039 (5) | −0.0046 (5) | −0.0004 (5) |
C16 | 0.0389 (9) | 0.0394 (8) | 0.0401 (10) | 0.0001 (7) | 0.0008 (8) | −0.0001 (8) |
C2 | 0.0563 (11) | 0.0425 (10) | 0.0576 (13) | 0.0038 (9) | −0.0086 (10) | −0.0140 (9) |
C12 | 0.0327 (8) | 0.0400 (8) | 0.0309 (8) | 0.0024 (7) | −0.0001 (7) | 0.0031 (7) |
C17 | 0.0344 (8) | 0.0467 (10) | 0.0387 (9) | 0.0008 (7) | −0.0029 (8) | 0.0012 (8) |
C9 | 0.0439 (10) | 0.0438 (9) | 0.0529 (12) | 0.0080 (8) | −0.0075 (9) | −0.0081 (9) |
C11 | 0.0369 (8) | 0.0365 (8) | 0.0380 (10) | 0.0006 (7) | −0.0036 (7) | 0.0011 (7) |
C15 | 0.0333 (8) | 0.0505 (9) | 0.0692 (15) | −0.0072 (9) | −0.0008 (10) | 0.0006 (10) |
C14 | 0.0320 (8) | 0.0411 (9) | 0.0456 (11) | 0.0032 (7) | −0.0063 (8) | 0.0016 (8) |
C1 | 0.0625 (12) | 0.0495 (10) | 0.0498 (12) | −0.0005 (9) | 0.0107 (10) | −0.0126 (10) |
C10 | 0.0426 (10) | 0.0398 (9) | 0.0621 (13) | −0.0073 (8) | −0.0022 (10) | 0.0062 (10) |
C13 | 0.0316 (7) | 0.0397 (8) | 0.0328 (9) | 0.0014 (7) | 0.0041 (7) | 0.0017 (7) |
O4 | 0.156 (2) | 0.0442 (9) | 0.1105 (19) | 0.0152 (11) | 0.0508 (17) | −0.0004 (11) |
C8 | 0.0644 (14) | 0.0529 (12) | 0.0852 (18) | 0.0172 (11) | −0.0225 (14) | −0.0283 (13) |
C6 | 0.0859 (16) | 0.0431 (10) | 0.0610 (14) | 0.0087 (11) | 0.0140 (14) | −0.0082 (10) |
C5 | 0.0764 (16) | 0.0672 (14) | 0.089 (2) | 0.0094 (12) | 0.0282 (16) | −0.0190 (15) |
C3 | 0.0869 (18) | 0.0480 (12) | 0.0814 (19) | −0.0108 (12) | 0.0080 (16) | −0.0010 (13) |
C4 | 0.0826 (18) | 0.0800 (16) | 0.097 (2) | −0.0172 (15) | 0.0362 (19) | −0.0135 (18) |
C7 | 0.196 (4) | 0.0599 (16) | 0.094 (3) | −0.013 (2) | 0.037 (3) | 0.0105 (18) |
O3 | 0.0483 (7) | 0.0418 (7) | 0.0431 (7) | 0.0082 (6) | 0.0041 (6) | 0.0046 (6) |
O2 | 0.0367 (6) | 0.0586 (8) | 0.0406 (7) | 0.0091 (6) | −0.0030 (6) | 0.0016 (7) |
O1—C14 | 1.437 (2) | C15—H15 | 0.9300 |
O1—C11 | 1.451 (2) | C14—C13 | 1.552 (3) |
C16—O3 | 1.428 (2) | C14—H14 | 0.9800 |
C16—C13 | 1.530 (2) | C1—C6 | 1.382 (3) |
C16—H16A | 0.9700 | C1—H1 | 0.9300 |
C16—H16B | 0.9700 | C10—H10 | 0.9300 |
C2—C3 | 1.373 (3) | C13—H13 | 0.9800 |
C2—C1 | 1.387 (3) | O4—C6 | 1.368 (3) |
C2—C8 | 1.511 (3) | O4—C7 | 1.399 (4) |
C12—C17 | 1.525 (2) | C8—H8A | 0.9700 |
C12—C11 | 1.574 (2) | C8—H8B | 0.9700 |
C12—C13 | 1.574 (2) | C6—C5 | 1.373 (4) |
C12—H12 | 0.9800 | C5—C4 | 1.365 (4) |
C17—O2 | 1.432 (2) | C5—H5 | 0.9300 |
C17—H17A | 0.9700 | C3—C4 | 1.386 (4) |
C17—H17B | 0.9700 | C3—H3 | 0.9300 |
C9—C11 | 1.513 (2) | C4—H4 | 0.9300 |
C9—C8 | 1.527 (3) | C7—H7A | 0.9600 |
C9—H9A | 0.9700 | C7—H7B | 0.9600 |
C9—H9B | 0.9700 | C7—H7C | 0.9600 |
C11—C10 | 1.523 (3) | O3—H3A | 0.8200 |
C15—C10 | 1.314 (3) | O2—H2 | 0.8200 |
C15—C14 | 1.513 (3) | ||
C14—O1—C11 | 96.39 (13) | C15—C14—H14 | 114.9 |
O3—C16—C13 | 112.27 (14) | C13—C14—H14 | 114.9 |
O3—C16—H16A | 109.2 | C6—C1—C2 | 120.2 (2) |
C13—C16—H16A | 109.2 | C6—C1—H1 | 119.9 |
O3—C16—H16B | 109.2 | C2—C1—H1 | 119.9 |
C13—C16—H16B | 109.2 | C15—C10—C11 | 106.37 (17) |
H16A—C16—H16B | 107.9 | C15—C10—H10 | 126.8 |
C3—C2—C1 | 118.8 (2) | C11—C10—H10 | 126.8 |
C3—C2—C8 | 120.9 (2) | C16—C13—C14 | 111.59 (15) |
C1—C2—C8 | 120.3 (2) | C16—C13—C12 | 115.11 (13) |
C17—C12—C11 | 114.31 (15) | C14—C13—C12 | 100.28 (13) |
C17—C12—C13 | 113.70 (14) | C16—C13—H13 | 109.8 |
C11—C12—C13 | 101.03 (13) | C14—C13—H13 | 109.8 |
C17—C12—H12 | 109.2 | C12—C13—H13 | 109.8 |
C11—C12—H12 | 109.2 | C6—O4—C7 | 118.3 (2) |
C13—C12—H12 | 109.2 | C2—C8—C9 | 113.20 (18) |
O2—C17—C12 | 112.39 (15) | C2—C8—H8A | 108.9 |
O2—C17—H17A | 109.1 | C9—C8—H8A | 108.9 |
C12—C17—H17A | 109.1 | C2—C8—H8B | 108.9 |
O2—C17—H17B | 109.1 | C9—C8—H8B | 108.9 |
C12—C17—H17B | 109.1 | H8A—C8—H8B | 107.8 |
H17A—C17—H17B | 107.9 | O4—C6—C5 | 115.2 (2) |
C11—C9—C8 | 112.05 (16) | O4—C6—C1 | 124.2 (2) |
C11—C9—H9A | 109.2 | C5—C6—C1 | 120.6 (2) |
C8—C9—H9A | 109.2 | C4—C5—C6 | 119.3 (2) |
C11—C9—H9B | 109.2 | C4—C5—H5 | 120.4 |
C8—C9—H9B | 109.2 | C6—C5—H5 | 120.4 |
H9A—C9—H9B | 107.9 | C2—C3—C4 | 120.5 (2) |
O1—C11—C9 | 111.07 (15) | C2—C3—H3 | 119.7 |
O1—C11—C10 | 101.51 (14) | C4—C3—H3 | 119.7 |
C9—C11—C10 | 117.20 (15) | C5—C4—C3 | 120.6 (3) |
O1—C11—C12 | 100.04 (12) | C5—C4—H4 | 119.7 |
C9—C11—C12 | 119.19 (15) | C3—C4—H4 | 119.7 |
C10—C11—C12 | 105.14 (15) | O4—C7—H7A | 109.5 |
C10—C15—C14 | 105.69 (18) | O4—C7—H7B | 109.5 |
C10—C15—H15 | 127.2 | H7A—C7—H7B | 109.5 |
C14—C15—H15 | 127.2 | O4—C7—H7C | 109.5 |
O1—C14—C15 | 102.48 (14) | H7A—C7—H7C | 109.5 |
O1—C14—C13 | 101.29 (13) | H7B—C7—H7C | 109.5 |
C15—C14—C13 | 106.85 (17) | C16—O3—H3A | 109.5 |
O1—C14—H14 | 114.9 | C17—O2—H2 | 109.5 |
C11—C12—C17—O2 | 75.2 (2) | O3—C16—C13—C14 | −56.0 (2) |
C13—C12—C17—O2 | −169.53 (15) | O3—C16—C13—C12 | −169.41 (15) |
C14—O1—C11—C9 | −173.54 (15) | O1—C14—C13—C16 | −85.19 (15) |
C14—O1—C11—C10 | −48.20 (15) | C15—C14—C13—C16 | 167.91 (14) |
C14—O1—C11—C12 | 59.66 (14) | O1—C14—C13—C12 | 37.20 (15) |
C8—C9—C11—O1 | 61.3 (2) | C15—C14—C13—C12 | −69.70 (16) |
C8—C9—C11—C10 | −54.7 (3) | C17—C12—C13—C16 | −3.9 (2) |
C8—C9—C11—C12 | 176.68 (19) | C11—C12—C13—C16 | 119.04 (16) |
C17—C12—C11—O1 | 87.36 (16) | C17—C12—C13—C14 | −123.77 (16) |
C13—C12—C11—O1 | −35.14 (15) | C11—C12—C13—C14 | −0.84 (16) |
C17—C12—C11—C9 | −33.8 (2) | C3—C2—C8—C9 | 72.7 (3) |
C13—C12—C11—C9 | −156.28 (16) | C1—C2—C8—C9 | −108.0 (3) |
C17—C12—C11—C10 | −167.70 (15) | C11—C9—C8—C2 | −179.5 (2) |
C13—C12—C11—C10 | 69.80 (16) | C7—O4—C6—C5 | −176.5 (3) |
C11—O1—C14—C15 | 49.05 (16) | C7—O4—C6—C1 | 4.1 (5) |
C11—O1—C14—C13 | −61.25 (13) | C2—C1—C6—O4 | 179.6 (3) |
C10—C15—C14—O1 | −32.1 (2) | C2—C1—C6—C5 | 0.3 (4) |
C10—C15—C14—C13 | 74.0 (2) | O4—C6—C5—C4 | −180.0 (3) |
C3—C2—C1—C6 | 0.8 (4) | C1—C6—C5—C4 | −0.6 (5) |
C8—C2—C1—C6 | −178.4 (2) | C1—C2—C3—C4 | −1.6 (4) |
C14—C15—C10—C11 | 0.5 (2) | C8—C2—C3—C4 | 177.7 (3) |
O1—C11—C10—C15 | 30.7 (2) | C6—C5—C4—C3 | −0.1 (5) |
C9—C11—C10—C15 | 151.8 (2) | C2—C3—C4—C5 | 1.2 (5) |
C12—C11—C10—C15 | −73.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O2i | 0.82 | 1.93 | 2.7409 (19) | 173 |
Symmetry code: (i) x+1/2, −y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C17H22O4 |
Mr | 290.35 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 294 |
a, b, c (Å) | 11.8025 (4), 14.9842 (4), 8.7569 (3) |
V (Å3) | 1548.67 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.43 × 0.27 × 0.24 |
Data collection | |
Diffractometer | Bruker APEX CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9219, 1915, 1719 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.652 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.084, 1.08 |
No. of reflections | 1915 |
No. of parameters | 193 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.16 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXL97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O2i | 0.82 | 1.93 | 2.7409 (19) | 172.7 |
Symmetry code: (i) x+1/2, −y+1, z. |
Furans are generally much less reactive dienes in Diels-Alder cycloaddition reaction due to their inherent aromaticity (Balaban et al., 2004) and usually facile retro- Diels-Alder reaction of the resulting adducts (Woodward, 1940). In view of the importance and great potential of Diels-Alder cycloadducts of furano derivatives as key intermediates for synthesizing structurally complex targets (Hudlicky et al., 1996) or achieving highly region-stereocontrolled reactions via the corresponding oxabicyclic adducts (Chiu & Lautens, 1997), a great deal of effort has been devoted to the development of chemical and physical means to promote the frequently difficult [4 + 2] cycloaddition of cyclic furano dienes. For example, Ultrasonic irradiation effectively promoted the Diels-Alder reaction of substituted furans with dimethyl maleate in very high exo selectivity (Wei, 2004) and the resulting product stereochemistry was unambiguously confirmed a single-crystal X-ray diffraction analysis (Fig. 1) of the corresponding reduction derivative diol (I). The oxidol bridge is on the same side as two hydroxymethyls, which are not parallel each other.
The molecules are linked by O···O hydrogen bonds to form a two-dimensional supramolecular network structure (Fig. 2). Inter-molecular O—H···O hydrogen bonding is observed between the O(3) and O(2) hydroxyl groups.