Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027110/xu2257sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027110/xu2257Isup2.hkl |
CCDC reference: 654921
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.038
- wR factor = 0.082
- Data-to-parameter ratio = 7.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.51 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
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 25.03 From the CIF: _reflns_number_total 2110 Count of symmetry unique reflns 2131 Completeness (_total/calc) 99.01% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 3 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 3 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 synthesized according to the procedure of Mikhailopulo & Sivets (1999). The title compound is obtained from methyl alpha/beta-D-arabinofuranoside, which reacted with trityl chloride in the presence of 4-(dimethylamino)pyridine in anhydride pyridine at 333–343 K for 6 h, after treatment and column chromatography (hexene-ethyl acetate 1:1, Rf 0.42) yield 45% as a white solid. The compound was crystallized from hexane-ethyl acetate (1:1) to yield colorless block-like crystals after a week at room temperature.
The hydroxyl H atoms were initially located in a difference Fourier map, and the position was allowed refined freely along with an isotropic displacement parameter. All other H-atoms were refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C) for aromatic, 0.97 Å, Uiso = 1.2Ueq (C) for CH2, and 0.96 Å, Uiso = 1.5Ueq (C) for CH3. And the methyl H was allowed to rotate freely about its C—C bond. In the absence of significant anomalous dispersion effects, Friedel pairs were merged.
The skeleton of the title compound, is composed of three benzene rings and a five-membered heterocyclic ring. And the five-membered ring have envelope conformations, with atom C2 at the flap of the envelope. It lie 0.484 (3) Å. The resultant puckering causes significant contractions of the C1—C2—C3 angles.
The title compound contains both intramolecular and intermolecular O—H···O hydrogen bonds. The intramolecule O—H···O hydrogen bonds join the compound to form a cage, and the intermolecule O—H···O hydrogen bonds link the molecules into infinite helical chains along the a axis.
For synthesis, see Mikhailopulo & Sivets (1999).
Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALE (Otwinowski & Minor, 1997); data reduction: SCALE; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C25H26O5 | F(000) = 864 |
Mr = 406.46 | Dx = 1.311 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 6994 reflections |
a = 7.4286 (15) Å | θ = 2.4–25.0° |
b = 8.1298 (16) Å | µ = 0.09 mm−1 |
c = 34.101 (7) Å | T = 295 K |
V = 2059.5 (7) Å3 | Block, colorless |
Z = 4 | 0.50 × 0.20 × 0.18 mm |
Rigaku R-AXIS RAPID IP diffractometer | 2110 independent reflections |
Radiation source: fine-focus sealed tube | 1522 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Detector resolution: 10 pixels mm-1 | θmax = 25.0°, θmin = 2.4° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −9→9 |
Tmin = 0.946, Tmax = 0.992 | l = −40→40 |
6994 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.082 | w = 1/[σ2(Fo2) + (0.0321P)2 + 0.285P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
2110 reflections | Δρmax = 0.15 e Å−3 |
281 parameters | Δρmin = −0.16 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0260 (15) |
C25H26O5 | V = 2059.5 (7) Å3 |
Mr = 406.46 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.4286 (15) Å | µ = 0.09 mm−1 |
b = 8.1298 (16) Å | T = 295 K |
c = 34.101 (7) Å | 0.50 × 0.20 × 0.18 mm |
Rigaku R-AXIS RAPID IP diffractometer | 2110 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1522 reflections with I > 2σ(I) |
Tmin = 0.946, Tmax = 0.992 | Rint = 0.043 |
6994 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 1 restraint |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.15 e Å−3 |
2110 reflections | Δρmin = −0.16 e Å−3 |
281 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 | ||
O1 | 0.5208 (3) | 0.5222 (3) | 0.08813 (6) | 0.0407 (6) | |
O2 | 0.4450 (3) | 0.6557 (3) | 0.02943 (6) | 0.0469 (6) | |
O3 | 0.6178 (4) | 0.2463 (3) | 0.03120 (7) | 0.0498 (7) | |
H3O | 0.646 (6) | 0.221 (5) | 0.0550 (7) | 0.080 (15)* | |
O4 | 0.1565 (3) | 0.3851 (3) | 0.04668 (7) | 0.0424 (6) | |
H4O | 0.143 (6) | 0.362 (6) | 0.0231 (10) | 0.081 (16)* | |
O5 | 0.5912 (3) | 0.2009 (2) | 0.11522 (5) | 0.0309 (5) | |
C1 | 0.5460 (5) | 0.5315 (4) | 0.04707 (9) | 0.0367 (8) | |
H1 | 0.6740 | 0.5455 | 0.0409 | 0.044* | |
C2 | 0.4782 (5) | 0.3666 (4) | 0.03127 (10) | 0.0361 (8) | |
H2 | 0.4307 | 0.3808 | 0.0047 | 0.043* | |
C3 | 0.3270 (4) | 0.3232 (4) | 0.05910 (8) | 0.0329 (8) | |
H3 | 0.3210 | 0.2038 | 0.0629 | 0.039* | |
C4 | 0.3786 (4) | 0.4081 (4) | 0.09739 (8) | 0.0340 (8) | |
H4 | 0.2744 | 0.4705 | 0.1069 | 0.041* | |
C5 | 0.4398 (4) | 0.2931 (4) | 0.12950 (8) | 0.0342 (8) | |
H5A | 0.4740 | 0.3555 | 0.1526 | 0.041* | |
H5B | 0.3428 | 0.2190 | 0.1366 | 0.041* | |
C6 | 0.5213 (6) | 0.8169 (4) | 0.03313 (10) | 0.0532 (11) | |
H6A | 0.4504 | 0.8940 | 0.0184 | 0.080* | |
H6B | 0.6422 | 0.8162 | 0.0232 | 0.080* | |
H6C | 0.5223 | 0.8486 | 0.0602 | 0.080* | |
C7 | 0.6897 (4) | 0.1002 (4) | 0.14349 (8) | 0.0287 (7) | |
C8 | 0.8065 (4) | −0.0140 (4) | 0.11786 (8) | 0.0272 (7) | |
C9 | 0.9242 (4) | 0.0581 (4) | 0.09055 (8) | 0.0344 (8) | |
H9 | 0.9268 | 0.1719 | 0.0878 | 0.041* | |
C10 | 1.0355 (5) | −0.0378 (4) | 0.06784 (9) | 0.0373 (8) | |
H10 | 1.1104 | 0.0116 | 0.0495 | 0.045* | |
C11 | 1.0372 (5) | −0.2078 (4) | 0.07207 (9) | 0.0382 (8) | |
H11 | 1.1138 | −0.2720 | 0.0569 | 0.046* | |
C12 | 0.9242 (5) | −0.2801 (4) | 0.09896 (9) | 0.0389 (9) | |
H12 | 0.9236 | −0.3939 | 0.1018 | 0.047* | |
C13 | 0.8107 (5) | −0.1839 (4) | 0.12205 (9) | 0.0360 (8) | |
H13 | 0.7367 | −0.2341 | 0.1405 | 0.043* | |
C14 | 0.5546 (4) | 0.0034 (4) | 0.16861 (8) | 0.0283 (7) | |
C15 | 0.4268 (4) | −0.0927 (4) | 0.15044 (9) | 0.0403 (8) | |
H15 | 0.4244 | −0.0973 | 0.1232 | 0.048* | |
C16 | 0.3028 (5) | −0.1820 (4) | 0.17135 (11) | 0.0485 (9) | |
H16 | 0.2173 | −0.2451 | 0.1583 | 0.058* | |
C17 | 0.3051 (5) | −0.1779 (4) | 0.21152 (11) | 0.0484 (9) | |
H17 | 0.2228 | −0.2397 | 0.2258 | 0.058* | |
C18 | 0.4296 (5) | −0.0822 (5) | 0.23045 (9) | 0.0482 (10) | |
H18 | 0.4312 | −0.0787 | 0.2577 | 0.058* | |
C19 | 0.5529 (4) | 0.0092 (4) | 0.20932 (8) | 0.0368 (8) | |
H19 | 0.6354 | 0.0752 | 0.2225 | 0.044* | |
C20 | 0.8215 (4) | 0.2061 (4) | 0.16746 (8) | 0.0292 (7) | |
C21 | 0.9461 (4) | 0.1301 (4) | 0.19168 (9) | 0.0377 (8) | |
H21 | 0.9453 | 0.0160 | 0.1938 | 0.045* | |
C22 | 1.0720 (5) | 0.2198 (4) | 0.21282 (10) | 0.0434 (9) | |
H22 | 1.1545 | 0.1660 | 0.2288 | 0.052* | |
C23 | 1.0741 (5) | 0.3882 (5) | 0.20995 (10) | 0.0488 (10) | |
H23 | 1.1571 | 0.4493 | 0.2243 | 0.059* | |
C24 | 0.9544 (5) | 0.4649 (4) | 0.18615 (10) | 0.0496 (10) | |
H24 | 0.9563 | 0.5791 | 0.1843 | 0.060* | |
C25 | 0.8290 (5) | 0.3765 (4) | 0.16445 (9) | 0.0393 (8) | |
H25 | 0.7499 | 0.4315 | 0.1479 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0557 (15) | 0.0316 (12) | 0.0348 (12) | −0.0128 (12) | −0.0050 (11) | −0.0004 (10) |
O2 | 0.0522 (15) | 0.0348 (13) | 0.0538 (14) | −0.0066 (13) | −0.0080 (14) | 0.0111 (12) |
O3 | 0.0535 (17) | 0.0537 (16) | 0.0423 (14) | 0.0193 (14) | 0.0049 (13) | −0.0082 (14) |
O4 | 0.0360 (13) | 0.0459 (14) | 0.0453 (14) | −0.0008 (13) | −0.0086 (13) | −0.0014 (13) |
O5 | 0.0290 (11) | 0.0362 (11) | 0.0274 (10) | 0.0041 (11) | 0.0000 (10) | 0.0036 (10) |
C1 | 0.0394 (19) | 0.0359 (18) | 0.0348 (18) | −0.0026 (18) | −0.0024 (18) | 0.0045 (16) |
C2 | 0.038 (2) | 0.0373 (19) | 0.0326 (18) | 0.0037 (17) | −0.0051 (16) | −0.0032 (16) |
C3 | 0.0318 (17) | 0.0281 (16) | 0.0387 (18) | 0.0008 (16) | −0.0057 (15) | −0.0022 (15) |
C4 | 0.0365 (19) | 0.0364 (18) | 0.0293 (16) | 0.0012 (17) | 0.0005 (15) | −0.0027 (15) |
C5 | 0.0310 (17) | 0.0401 (18) | 0.0313 (16) | 0.0024 (18) | 0.0041 (15) | 0.0025 (15) |
C6 | 0.070 (3) | 0.0360 (19) | 0.053 (2) | −0.008 (2) | 0.000 (2) | 0.0026 (18) |
C7 | 0.0275 (16) | 0.0317 (16) | 0.0268 (15) | −0.0019 (17) | −0.0012 (14) | 0.0045 (15) |
C8 | 0.0279 (17) | 0.0272 (16) | 0.0266 (16) | −0.0010 (15) | −0.0030 (15) | −0.0016 (15) |
C9 | 0.0351 (19) | 0.0325 (18) | 0.0355 (17) | −0.0028 (16) | 0.0047 (17) | 0.0049 (15) |
C10 | 0.0305 (18) | 0.043 (2) | 0.0383 (18) | −0.0027 (17) | 0.0033 (17) | 0.0045 (16) |
C11 | 0.0379 (19) | 0.0405 (19) | 0.0362 (18) | 0.0052 (18) | 0.0019 (18) | −0.0058 (17) |
C12 | 0.043 (2) | 0.0292 (17) | 0.0451 (19) | 0.0038 (18) | −0.0015 (18) | −0.0005 (16) |
C13 | 0.0361 (19) | 0.0360 (18) | 0.0361 (19) | −0.0024 (17) | 0.0023 (17) | 0.0023 (17) |
C14 | 0.0262 (16) | 0.0291 (16) | 0.0295 (16) | −0.0009 (17) | 0.0023 (14) | 0.0038 (15) |
C15 | 0.0337 (18) | 0.053 (2) | 0.0346 (18) | −0.011 (2) | 0.0013 (16) | 0.0028 (18) |
C16 | 0.039 (2) | 0.050 (2) | 0.057 (2) | −0.014 (2) | 0.0022 (19) | 0.003 (2) |
C17 | 0.039 (2) | 0.047 (2) | 0.059 (2) | −0.008 (2) | 0.011 (2) | 0.017 (2) |
C18 | 0.053 (2) | 0.060 (2) | 0.0310 (17) | −0.001 (2) | 0.0077 (18) | 0.0144 (19) |
C19 | 0.0364 (18) | 0.0429 (19) | 0.0311 (17) | −0.0034 (19) | −0.0024 (16) | 0.0024 (17) |
C20 | 0.0275 (16) | 0.0304 (17) | 0.0298 (16) | −0.0046 (16) | 0.0021 (15) | 0.0008 (15) |
C21 | 0.0364 (19) | 0.0338 (18) | 0.0428 (18) | 0.0004 (17) | −0.0047 (18) | −0.0015 (16) |
C22 | 0.0326 (19) | 0.053 (2) | 0.0442 (19) | 0.000 (2) | −0.0094 (18) | −0.0020 (19) |
C23 | 0.047 (2) | 0.052 (2) | 0.048 (2) | −0.014 (2) | −0.010 (2) | −0.009 (2) |
C24 | 0.060 (3) | 0.0329 (19) | 0.056 (2) | −0.014 (2) | −0.009 (2) | −0.0010 (18) |
C25 | 0.043 (2) | 0.0362 (18) | 0.0391 (19) | −0.0064 (19) | −0.0057 (18) | 0.0043 (16) |
O1—C1 | 1.415 (3) | C10—C11 | 1.390 (4) |
O1—C4 | 1.441 (4) | C10—H10 | 0.9300 |
O2—C1 | 1.395 (4) | C11—C12 | 1.375 (4) |
O2—C6 | 1.434 (4) | C11—H11 | 0.9300 |
O3—C2 | 1.425 (4) | C12—C13 | 1.394 (4) |
O3—H3O | 0.863 (19) | C12—H12 | 0.9300 |
O4—C3 | 1.427 (4) | C13—H13 | 0.9300 |
O4—H4O | 0.83 (4) | C14—C15 | 1.377 (4) |
O5—C5 | 1.437 (4) | C14—C19 | 1.389 (4) |
O5—C7 | 1.461 (3) | C15—C16 | 1.372 (4) |
C1—C2 | 1.530 (4) | C15—H15 | 0.9300 |
C1—H1 | 0.9800 | C16—C17 | 1.371 (4) |
C2—C3 | 1.512 (4) | C16—H16 | 0.9300 |
C2—H2 | 0.9800 | C17—C18 | 1.370 (5) |
C3—C4 | 1.526 (4) | C17—H17 | 0.9300 |
C3—H3 | 0.9800 | C18—C19 | 1.382 (4) |
C4—C5 | 1.510 (4) | C18—H18 | 0.9300 |
C4—H4 | 0.9800 | C19—H19 | 0.9300 |
C5—H5A | 0.9700 | C20—C21 | 1.386 (4) |
C5—H5B | 0.9700 | C20—C25 | 1.390 (4) |
C6—H6A | 0.9600 | C21—C22 | 1.388 (4) |
C6—H6B | 0.9600 | C21—H21 | 0.9300 |
C6—H6C | 0.9600 | C22—C23 | 1.373 (5) |
C7—C14 | 1.536 (4) | C22—H22 | 0.9300 |
C7—C20 | 1.539 (4) | C23—C24 | 1.356 (5) |
C7—C8 | 1.543 (4) | C23—H23 | 0.9300 |
C8—C13 | 1.388 (4) | C24—C25 | 1.390 (4) |
C8—C9 | 1.405 (4) | C24—H24 | 0.9300 |
C9—C10 | 1.375 (4) | C25—H25 | 0.9300 |
C9—H9 | 0.9300 | ||
C1—O1—C4 | 110.4 (2) | C10—C9—H9 | 119.7 |
C1—O2—C6 | 114.3 (3) | C8—C9—H9 | 119.7 |
C2—O3—H3O | 110 (3) | C9—C10—C11 | 120.7 (3) |
C3—O4—H4O | 108 (3) | C9—C10—H10 | 119.6 |
C5—O5—C7 | 117.4 (2) | C11—C10—H10 | 119.6 |
O2—C1—O1 | 113.3 (3) | C12—C11—C10 | 119.3 (3) |
O2—C1—C2 | 107.8 (3) | C12—C11—H11 | 120.4 |
O1—C1—C2 | 105.0 (3) | C10—C11—H11 | 120.4 |
O2—C1—H1 | 110.2 | C11—C12—C13 | 120.4 (3) |
O1—C1—H1 | 110.2 | C11—C12—H12 | 119.8 |
C2—C1—H1 | 110.2 | C13—C12—H12 | 119.8 |
O3—C2—C3 | 112.4 (3) | C8—C13—C12 | 120.9 (3) |
O3—C2—C1 | 111.2 (3) | C8—C13—H13 | 119.6 |
C3—C2—C1 | 103.2 (3) | C12—C13—H13 | 119.6 |
O3—C2—H2 | 109.9 | C15—C14—C19 | 117.5 (3) |
C3—C2—H2 | 109.9 | C15—C14—C7 | 119.4 (3) |
C1—C2—H2 | 109.9 | C19—C14—C7 | 123.1 (3) |
O4—C3—C2 | 113.0 (2) | C16—C15—C14 | 122.0 (3) |
O4—C3—C4 | 108.5 (3) | C16—C15—H15 | 119.0 |
C2—C3—C4 | 104.2 (3) | C14—C15—H15 | 119.0 |
O4—C3—H3 | 110.3 | C17—C16—C15 | 119.9 (3) |
C2—C3—H3 | 110.3 | C17—C16—H16 | 120.1 |
C4—C3—H3 | 110.3 | C15—C16—H16 | 120.1 |
O1—C4—C5 | 109.7 (2) | C16—C17—C18 | 119.6 (3) |
O1—C4—C3 | 106.7 (2) | C16—C17—H17 | 120.2 |
C5—C4—C3 | 114.6 (3) | C18—C17—H17 | 120.2 |
O1—C4—H4 | 108.6 | C17—C18—C19 | 120.5 (3) |
C5—C4—H4 | 108.6 | C17—C18—H18 | 119.8 |
C3—C4—H4 | 108.6 | C19—C18—H18 | 119.8 |
O5—C5—C4 | 108.3 (2) | C18—C19—C14 | 120.6 (3) |
O5—C5—H5A | 110.0 | C18—C19—H19 | 119.7 |
C4—C5—H5A | 110.0 | C14—C19—H19 | 119.7 |
O5—C5—H5B | 110.0 | C21—C20—C25 | 117.5 (3) |
C4—C5—H5B | 110.0 | C21—C20—C7 | 119.4 (3) |
H5A—C5—H5B | 108.4 | C25—C20—C7 | 122.9 (3) |
O2—C6—H6A | 109.5 | C20—C21—C22 | 121.7 (3) |
O2—C6—H6B | 109.5 | C20—C21—H21 | 119.2 |
H6A—C6—H6B | 109.5 | C22—C21—H21 | 119.2 |
O2—C6—H6C | 109.5 | C23—C22—C21 | 119.7 (4) |
H6A—C6—H6C | 109.5 | C23—C22—H22 | 120.2 |
H6B—C6—H6C | 109.5 | C21—C22—H22 | 120.2 |
O5—C7—C14 | 109.2 (2) | C24—C23—C22 | 119.6 (3) |
O5—C7—C20 | 110.8 (2) | C24—C23—H23 | 120.2 |
C14—C7—C20 | 114.0 (2) | C22—C23—H23 | 120.2 |
O5—C7—C8 | 104.2 (2) | C23—C24—C25 | 121.3 (3) |
C14—C7—C8 | 112.1 (3) | C23—C24—H24 | 119.3 |
C20—C7—C8 | 106.2 (2) | C25—C24—H24 | 119.3 |
C13—C8—C9 | 118.0 (3) | C20—C25—C24 | 120.2 (3) |
C13—C8—C7 | 123.5 (3) | C20—C25—H25 | 119.9 |
C9—C8—C7 | 118.3 (3) | C24—C25—H25 | 119.9 |
C10—C9—C8 | 120.7 (3) | ||
C6—O2—C1—O1 | 79.8 (4) | C9—C10—C11—C12 | 0.8 (6) |
C6—O2—C1—C2 | −164.6 (3) | C10—C11—C12—C13 | −0.7 (5) |
C4—O1—C1—O2 | 91.9 (3) | C9—C8—C13—C12 | −1.9 (5) |
C4—O1—C1—C2 | −25.4 (3) | C7—C8—C13—C12 | −177.6 (3) |
O2—C1—C2—O3 | 151.1 (3) | C11—C12—C13—C8 | 1.3 (5) |
O1—C1—C2—O3 | −87.9 (3) | O5—C7—C14—C15 | 53.9 (4) |
O2—C1—C2—C3 | −88.2 (3) | C20—C7—C14—C15 | 178.4 (3) |
O1—C1—C2—C3 | 32.8 (3) | C8—C7—C14—C15 | −60.9 (4) |
O3—C2—C3—O4 | −150.2 (3) | O5—C7—C14—C19 | −125.3 (3) |
C1—C2—C3—O4 | 89.9 (3) | C20—C7—C14—C19 | −0.8 (4) |
O3—C2—C3—C4 | 92.3 (3) | C8—C7—C14—C19 | 119.9 (3) |
C1—C2—C3—C4 | −27.7 (3) | C19—C14—C15—C16 | −0.9 (5) |
C1—O1—C4—C5 | 132.3 (3) | C7—C14—C15—C16 | 179.9 (3) |
C1—O1—C4—C3 | 7.6 (3) | C14—C15—C16—C17 | −0.5 (6) |
O4—C3—C4—O1 | −107.2 (3) | C15—C16—C17—C18 | 1.1 (6) |
C2—C3—C4—O1 | 13.5 (3) | C16—C17—C18—C19 | −0.3 (5) |
O4—C3—C4—C5 | 131.3 (3) | C17—C18—C19—C14 | −1.1 (5) |
C2—C3—C4—C5 | −108.1 (3) | C15—C14—C19—C18 | 1.7 (5) |
C7—O5—C5—C4 | 170.8 (2) | C7—C14—C19—C18 | −179.2 (3) |
O1—C4—C5—O5 | −62.1 (3) | O5—C7—C20—C21 | −170.5 (3) |
C3—C4—C5—O5 | 57.8 (3) | C14—C7—C20—C21 | 66.0 (4) |
C5—O5—C7—C14 | 45.8 (3) | C8—C7—C20—C21 | −57.9 (4) |
C5—O5—C7—C20 | −80.5 (3) | O5—C7—C20—C25 | 5.8 (4) |
C5—O5—C7—C8 | 165.7 (2) | C14—C7—C20—C25 | −117.7 (4) |
O5—C7—C8—C13 | −128.3 (3) | C8—C7—C20—C25 | 118.4 (3) |
C14—C7—C8—C13 | −10.4 (4) | C25—C20—C21—C22 | 1.2 (5) |
C20—C7—C8—C13 | 114.6 (3) | C7—C20—C21—C22 | 177.7 (3) |
O5—C7—C8—C9 | 56.1 (3) | C20—C21—C22—C23 | 0.2 (5) |
C14—C7—C8—C9 | 174.0 (3) | C21—C22—C23—C24 | −0.8 (6) |
C20—C7—C8—C9 | −61.0 (3) | C22—C23—C24—C25 | 0.0 (6) |
C13—C8—C9—C10 | 2.1 (5) | C21—C20—C25—C24 | −1.9 (5) |
C7—C8—C9—C10 | 177.9 (3) | C7—C20—C25—C24 | −178.3 (3) |
C8—C9—C10—C11 | −1.6 (5) | C23—C24—C25—C20 | 1.4 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O5 | 0.86 (2) | 2.10 (3) | 2.896 (3) | 153 (4) |
O4—H4O···O3i | 0.83 (4) | 2.06 (4) | 2.877 (3) | 168 (4) |
Symmetry code: (i) x−1/2, −y+1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C25H26O5 |
Mr | 406.46 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 295 |
a, b, c (Å) | 7.4286 (15), 8.1298 (16), 34.101 (7) |
V (Å3) | 2059.5 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.946, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6994, 2110, 1522 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.082, 1.01 |
No. of reflections | 2110 |
No. of parameters | 281 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.15, −0.16 |
Computer programs: DENZO (Otwinowski & Minor, 1997), SCALE (Otwinowski & Minor, 1997), SCALE, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O5 | 0.863 (19) | 2.10 (3) | 2.896 (3) | 153 (4) |
O4—H4O···O3i | 0.83 (4) | 2.06 (4) | 2.877 (3) | 168 (4) |
Symmetry code: (i) x−1/2, −y+1/2, −z. |
The skeleton of the title compound, is composed of three benzene rings and a five-membered heterocyclic ring. And the five-membered ring have envelope conformations, with atom C2 at the flap of the envelope. It lie 0.484 (3) Å. The resultant puckering causes significant contractions of the C1—C2—C3 angles.
The title compound contains both intramolecular and intermolecular O—H···O hydrogen bonds. The intramolecule O—H···O hydrogen bonds join the compound to form a cage, and the intermolecule O—H···O hydrogen bonds link the molecules into infinite helical chains along the a axis.