Buy article online - an online subscription or single-article purchase is required to access this article.
The crystal structure of the title compound, C
20H
22O
6·C
4H
8O
2, has been determined. The crystals are stabilized by O—H
O hydrogen bonding between the pinoresinol and dioxane molecules. C—H
O hydrogen bonds are absent, but are present in a previously reported polymorph of the solvate. The formation of two polymorphs may be related to different hydrogen-bonding possibilities. The five-membered rings in the central dioxabicyclooctane ring system of the pinoresinol molecules in the title compound are twisted on the benzylic C and the O atom.
Supporting information
CCDC reference: 232156
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.007 Å
- R factor = 0.043
- wR factor = 0.177
- Data-to-parameter ratio = 7.1
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given . ?
| Author Response: There is no anomalous signal in the data, but the assignment
is
described in the text.
|
Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 93 PerFit
PLAT112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem... a
PLAT113_ALERT_2_B ADDSYM Suggests Possible Pseudo/New Spacegroup . P21/c
Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.10
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
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 25.00
From the CIF: _reflns_number_total 2079
Count of symmetry unique reflns 2081
Completeness (_total/calc) 99.90%
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
1 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 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
Data collection: TEXRAY (Molecular Structure Corporation, 1985); cell refinement: TEXRAY; data reduction: TEXRAY; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL.
(+)-pinoresinol–dioxane (1/1)
top
Crystal data top
C20H22O6·C4H8O2 | F(000) = 476 |
Mr = 446.48 | Dx = 1.360 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2yb | Cell parameters from 23 reflections |
a = 7.836 (3) Å | θ = 19.9–22.6° |
b = 7.8011 (14) Å | µ = 0.10 mm−1 |
c = 17.923 (7) Å | T = 153 K |
β = 95.48 (3)° | Plate, colourless |
V = 1090.5 (6) Å3 | 0.55 × 0.49 × 0.28 mm |
Z = 2 | |
Data collection top
Rigaku AFC-6 diffractometer | Rint = 0.079 |
Radiation source: normal-focus rotating anode | θmax = 25.0°, θmin = 2.3° |
Graphite monochromator | h = 0→9 |
2θ–ω scans | k = 0→9 |
2240 measured reflections | l = −21→21 |
2079 independent reflections | 3 standard reflections every 150 reflections |
1616 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.177 | H-atom parameters constrained |
S = 1.17 | w = 1/[σ2(Fo2) + (0.122P)2 + 0.0693P] where P = (Fo2 + 2Fc2)/3 |
2079 reflections | (Δ/σ)max < 0.001 |
293 parameters | Δρmax = 0.31 e Å−3 |
1 restraint | Δρmin = −0.35 e Å−3 |
Special details top
Experimental. Data were collected at low temperature using a Rigaku AFC6R
diffractometer equiped with a low temperature device. The data were collected
using 2θ-ω-scan. Scans of (1.70 + 0.30tanθ) were made at a speed of
8.0ο/min in ω. The weak reflections (I<10.0σI) were rescanned (maximum 3
rescans) and the counts were accumulated to assure good counting statistics.
Stationary bacground counts were recored on each side of the reflection. The
ratio of peak counting time to backgroud counting time was 2:1. The
crystal–to–detector distance was 400 mm. |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.8513 (6) | 0.6461 (7) | −0.1577 (3) | 0.0337 (10) | |
C2 | 1.0006 (6) | 0.7092 (6) | −0.1844 (2) | 0.0304 (10) | |
H2 | 1.0927 | 0.7492 | −0.1505 | 0.040* | |
C3 | 1.0126 (5) | 0.7127 (6) | −0.2612 (3) | 0.0308 (10) | |
C4 | 0.8772 (5) | 0.6567 (6) | −0.3114 (2) | 0.0304 (10) | |
C5 | 0.7312 (6) | 0.5938 (7) | −0.2834 (3) | 0.0367 (11) | |
H5 | 0.6381 | 0.5544 | −0.3168 | 0.048* | |
C6 | 0.7197 (6) | 0.5880 (7) | −0.2059 (3) | 0.0372 (11) | |
H6 | 0.6195 | 0.5433 | −0.1870 | 0.048* | |
C7 | 1.2999 (6) | 0.8135 (9) | −0.2470 (3) | 0.0488 (14) | |
H7A | 1.2731 | 0.9087 | −0.2144 | 0.063* | |
H7B | 1.3923 | 0.8477 | −0.2770 | 0.063* | |
H7C | 1.3364 | 0.7139 | −0.2162 | 0.063* | |
C8 | 0.8321 (6) | 0.6425 (7) | −0.0736 (3) | 0.0357 (11) | |
H8 | 0.7873 | 0.5275 | −0.0603 | 0.046* | |
C9 | 0.7175 (6) | 0.7813 (7) | −0.0441 (3) | 0.0362 (11) | |
H9 | 0.7302 | 0.8926 | −0.0706 | 0.047* | |
C10 | 0.5284 (7) | 0.7329 (9) | −0.0430 (3) | 0.0484 (15) | |
H10A | 0.4547 | 0.8110 | −0.0755 | 0.063* | |
H10B | 0.5083 | 0.6139 | −0.0608 | 0.063* | |
C11 | 0.6322 (5) | 0.7423 (6) | 0.1593 (2) | 0.0305 (10) | |
C12 | 0.4851 (6) | 0.6874 (6) | 0.1905 (2) | 0.0299 (10) | |
H12 | 0.3936 | 0.6363 | 0.1597 | 0.039* | |
C13 | 0.4731 (5) | 0.7075 (6) | 0.2666 (2) | 0.0277 (10) | |
C14 | 0.6085 (5) | 0.7797 (6) | 0.3124 (2) | 0.0285 (10) | |
C15 | 0.7515 (6) | 0.8347 (7) | 0.2805 (3) | 0.0353 (11) | |
H15 | 0.8433 | 0.8857 | 0.3111 | 0.046* | |
C16 | 0.7635 (6) | 0.8167 (7) | 0.2040 (3) | 0.0343 (11) | |
H16 | 0.8628 | 0.8560 | 0.1827 | 0.045* | |
C17 | 0.1863 (6) | 0.6061 (9) | 0.2582 (3) | 0.0478 (14) | |
H17A | 0.1505 | 0.6965 | 0.2220 | 0.062* | |
H17B | 0.0938 | 0.5835 | 0.2900 | 0.062* | |
H17C | 0.2118 | 0.5013 | 0.2312 | 0.062* | |
C18 | 0.6471 (6) | 0.7052 (7) | 0.0771 (3) | 0.0357 (11) | |
H18 | 0.6643 | 0.5789 | 0.0719 | 0.046* | |
C19 | 0.7853 (6) | 0.7947 (7) | 0.0384 (2) | 0.0354 (11) | |
H19 | 0.7976 | 0.9171 | 0.0546 | 0.046* | |
C20 | 0.9606 (7) | 0.7037 (8) | 0.0437 (3) | 0.0422 (13) | |
H20A | 1.0508 | 0.7784 | 0.0687 | 0.055* | |
H20B | 0.9565 | 0.5958 | 0.0725 | 0.055* | |
C21 | 0.2802 (5) | 0.8879 (7) | 0.5416 (3) | 0.0341 (10) | |
H21A | 0.2930 | 0.9546 | 0.5888 | 0.044* | |
H21B | 0.3029 | 0.9655 | 0.5000 | 0.044* | |
C22 | 0.4070 (6) | 0.7436 (7) | 0.5462 (2) | 0.0331 (11) | |
H22A | 0.5248 | 0.7905 | 0.5541 | 0.043* | |
H22B | 0.3882 | 0.6695 | 0.5895 | 0.043* | |
C23 | 0.2183 (5) | 0.5772 (7) | 0.4673 (3) | 0.0331 (10) | |
H23A | 0.1964 | 0.5012 | 0.5095 | 0.043* | |
H23B | 0.2053 | 0.5087 | 0.4206 | 0.043* | |
C24 | 0.0912 (5) | 0.7217 (7) | 0.4619 (2) | 0.0314 (10) | |
H24A | 0.1107 | 0.7954 | 0.4185 | 0.041* | |
H24B | −0.0265 | 0.6748 | 0.4537 | 0.041* | |
O1 | 1.1517 (4) | 0.7704 (5) | −0.29529 (17) | 0.0371 (9) | |
O2 | 0.8858 (4) | 0.6592 (5) | −0.38699 (17) | 0.0388 (8) | |
H2A | 0.9743 | 0.7123 | −0.3967 | 0.050* | |
O3 | 0.9950 (5) | 0.6688 (6) | −0.03226 (19) | 0.0471 (10) | |
O4 | 0.4916 (4) | 0.7492 (6) | 0.03384 (18) | 0.0459 (10) | |
O5 | 0.3342 (4) | 0.6595 (5) | 0.30313 (17) | 0.0361 (8) | |
O6 | 0.5999 (4) | 0.8015 (5) | 0.38769 (16) | 0.0352 (8) | |
H6A | 0.5247 | 0.7360 | 0.4023 | 0.046* | |
O7 | 0.1079 (3) | 0.8221 (5) | 0.52925 (17) | 0.0332 (8) | |
O8 | 0.3891 (3) | 0.6439 (5) | 0.47870 (16) | 0.0329 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.037 (2) | 0.030 (2) | 0.036 (2) | 0.006 (2) | 0.0134 (19) | 0.004 (2) |
C2 | 0.033 (2) | 0.034 (2) | 0.025 (2) | 0.004 (2) | 0.0071 (18) | −0.0001 (19) |
C3 | 0.031 (2) | 0.030 (2) | 0.033 (2) | 0.0002 (19) | 0.0123 (19) | −0.001 (2) |
C4 | 0.035 (2) | 0.029 (2) | 0.029 (2) | 0.001 (2) | 0.0101 (18) | −0.004 (2) |
C5 | 0.033 (2) | 0.040 (3) | 0.038 (3) | −0.006 (2) | 0.008 (2) | −0.007 (2) |
C6 | 0.038 (2) | 0.039 (3) | 0.038 (3) | −0.003 (2) | 0.017 (2) | −0.001 (2) |
C7 | 0.038 (3) | 0.065 (4) | 0.044 (3) | −0.018 (3) | 0.009 (2) | −0.013 (3) |
C8 | 0.037 (2) | 0.035 (2) | 0.037 (3) | 0.008 (2) | 0.0119 (19) | 0.002 (2) |
C9 | 0.046 (2) | 0.038 (3) | 0.027 (2) | 0.009 (2) | 0.0131 (19) | 0.0013 (19) |
C10 | 0.045 (3) | 0.070 (4) | 0.031 (3) | 0.013 (3) | 0.010 (2) | −0.003 (3) |
C11 | 0.035 (2) | 0.029 (2) | 0.029 (2) | 0.001 (2) | 0.0104 (18) | −0.004 (2) |
C12 | 0.035 (2) | 0.030 (2) | 0.025 (2) | −0.002 (2) | 0.0047 (18) | −0.0029 (18) |
C13 | 0.032 (2) | 0.027 (2) | 0.025 (2) | 0.0011 (19) | 0.0079 (18) | −0.0020 (18) |
C14 | 0.032 (2) | 0.031 (2) | 0.024 (2) | 0.001 (2) | 0.0033 (17) | 0.0007 (19) |
C15 | 0.033 (2) | 0.036 (3) | 0.037 (3) | −0.005 (2) | 0.007 (2) | −0.004 (2) |
C16 | 0.034 (2) | 0.037 (3) | 0.034 (2) | 0.001 (2) | 0.0137 (19) | 0.004 (2) |
C17 | 0.030 (2) | 0.070 (4) | 0.043 (3) | −0.014 (3) | 0.005 (2) | −0.001 (3) |
C18 | 0.037 (2) | 0.036 (3) | 0.035 (3) | 0.001 (2) | 0.0089 (19) | 0.001 (2) |
C19 | 0.046 (2) | 0.035 (2) | 0.027 (2) | −0.003 (2) | 0.0113 (18) | −0.001 (2) |
C20 | 0.043 (3) | 0.053 (3) | 0.032 (3) | 0.001 (3) | 0.012 (2) | 0.004 (2) |
C21 | 0.031 (2) | 0.036 (3) | 0.036 (3) | −0.006 (2) | 0.0054 (18) | −0.001 (2) |
C22 | 0.031 (2) | 0.042 (3) | 0.025 (2) | −0.004 (2) | −0.0024 (18) | 0.001 (2) |
C23 | 0.031 (2) | 0.035 (2) | 0.034 (2) | −0.007 (2) | 0.0066 (18) | −0.002 (2) |
C24 | 0.029 (2) | 0.040 (3) | 0.025 (2) | −0.004 (2) | 0.0008 (17) | 0.001 (2) |
O1 | 0.0297 (15) | 0.051 (2) | 0.0314 (17) | −0.0103 (16) | 0.0078 (13) | −0.0041 (15) |
O2 | 0.0361 (17) | 0.050 (2) | 0.0312 (17) | −0.0113 (17) | 0.0090 (13) | −0.0034 (16) |
O3 | 0.0432 (19) | 0.068 (3) | 0.0320 (18) | 0.011 (2) | 0.0134 (15) | 0.0007 (19) |
O4 | 0.0374 (17) | 0.073 (3) | 0.0276 (17) | 0.0099 (19) | 0.0069 (13) | −0.0083 (18) |
O5 | 0.0286 (15) | 0.050 (2) | 0.0312 (17) | −0.0101 (16) | 0.0088 (13) | −0.0045 (16) |
O6 | 0.0368 (17) | 0.0422 (19) | 0.0278 (16) | −0.0108 (16) | 0.0085 (13) | −0.0036 (15) |
O7 | 0.0280 (15) | 0.0398 (18) | 0.0330 (16) | 0.0001 (14) | 0.0090 (13) | −0.0031 (15) |
O8 | 0.0274 (15) | 0.0417 (19) | 0.0300 (16) | −0.0008 (15) | 0.0059 (12) | −0.0003 (15) |
Geometric parameters (Å, º) top
C1—C2 | 1.395 (6) | C14—C15 | 1.374 (6) |
C1—C6 | 1.359 (7) | C15—C16 | 1.391 (6) |
C1—C8 | 1.528 (6) | C15—H15 | 0.9500 |
C2—C3 | 1.389 (6) | C16—H16 | 0.9500 |
C2—H2 | 0.9500 | C17—O5 | 1.410 (6) |
C3—O1 | 1.375 (5) | C17—H17A | 0.9800 |
C3—C4 | 1.394 (6) | C17—H17B | 0.9800 |
C4—O2 | 1.364 (5) | C17—H17C | 0.9800 |
C4—C5 | 1.383 (6) | C18—O4 | 1.423 (6) |
C5—C6 | 1.401 (6) | C18—C19 | 1.512 (6) |
C5—H5 | 0.9500 | C18—H18 | 1.0000 |
C6—H6 | 0.9500 | C19—C20 | 1.541 (7) |
C7—O1 | 1.421 (5) | C19—H19 | 1.0000 |
C7—H7A | 0.9800 | C20—O3 | 1.438 (6) |
C7—H7B | 0.9800 | C20—H20A | 0.9900 |
C7—H7C | 0.9800 | C20—H20B | 0.9900 |
C8—O3 | 1.429 (6) | C21—O7 | 1.441 (5) |
C8—C9 | 1.533 (7) | C21—C22 | 1.498 (7) |
C8—H8 | 1.0000 | C21—H21A | 0.9900 |
C9—C19 | 1.525 (7) | C21—H21B | 0.9900 |
C9—C10 | 1.531 (7) | C22—O8 | 1.434 (6) |
C9—H9 | 1.0000 | C22—H22A | 0.9900 |
C10—O4 | 1.439 (5) | C22—H22B | 0.9900 |
C10—H10A | 0.9900 | C23—O8 | 1.432 (5) |
C10—H10B | 0.9900 | C23—C24 | 1.501 (7) |
C11—C16 | 1.371 (6) | C23—H23A | 0.9900 |
C11—C12 | 1.396 (6) | C23—H23B | 0.9900 |
C11—C18 | 1.515 (6) | C24—O7 | 1.435 (6) |
C12—C13 | 1.385 (6) | C24—H24A | 0.9900 |
C12—H12 | 0.9500 | C24—H24B | 0.9900 |
C13—O5 | 1.374 (5) | O2—H2A | 0.8400 |
C13—C14 | 1.397 (6) | O6—H6A | 0.8400 |
C14—O6 | 1.368 (5) | | |
| | | |
C2—C1—C6 | 120.6 (4) | C11—C16—H16 | 119.9 |
C2—C1—C8 | 120.7 (4) | C15—C16—H16 | 119.9 |
C6—C1—C8 | 118.7 (4) | O5—C17—H17A | 109.5 |
C1—C2—C3 | 119.1 (4) | O5—C17—H17B | 109.5 |
C1—C2—H2 | 120.5 | H17A—C17—H17B | 109.5 |
C3—C2—H2 | 120.5 | O5—C17—H17C | 109.5 |
O1—C3—C2 | 125.4 (4) | H17A—C17—H17C | 109.5 |
O1—C3—C4 | 113.7 (4) | H17B—C17—H17C | 109.5 |
C2—C3—C4 | 120.9 (4) | O4—C18—C19 | 104.6 (4) |
O2—C4—C3 | 122.0 (4) | O4—C18—C11 | 110.0 (4) |
O2—C4—C5 | 119.2 (4) | C19—C18—C11 | 118.9 (4) |
C3—C4—C5 | 118.8 (4) | O4—C18—H18 | 107.6 |
C6—C5—C4 | 120.3 (4) | C19—C18—H18 | 107.6 |
C6—C5—H5 | 119.8 | C11—C18—H18 | 107.6 |
C4—C5—H5 | 119.8 | C9—C19—C18 | 102.4 (4) |
C5—C6—C1 | 120.2 (4) | C9—C19—C20 | 104.7 (4) |
C5—C6—H6 | 119.9 | C18—C19—C20 | 115.6 (4) |
C1—C6—H6 | 119.9 | C9—C19—H19 | 111.2 |
O1—C7—H7A | 109.5 | C18—C19—H19 | 111.2 |
O1—C7—H7B | 109.5 | C20—C19—H19 | 111.2 |
H7A—C7—H7B | 109.5 | O3—C20—C19 | 106.0 (4) |
O1—C7—H7C | 109.5 | O3—C20—H20A | 110.5 |
H7A—C7—H7C | 109.5 | C19—C20—H20A | 110.5 |
H7B—C7—H7C | 109.5 | O3—C20—H20B | 110.5 |
O3—C8—C9 | 104.1 (4) | C19—C20—H20B | 110.5 |
O3—C8—C1 | 109.9 (4) | H20A—C20—H20B | 108.7 |
C9—C8—C1 | 116.3 (4) | O7—C21—C22 | 110.3 (4) |
O3—C8—H8 | 108.7 | O7—C21—H21A | 109.6 |
C9—C8—H8 | 108.7 | C22—C21—H21A | 109.6 |
C1—C8—H8 | 108.7 | O7—C21—H21B | 109.6 |
C19—C9—C8 | 102.8 (4) | C22—C21—H21B | 109.6 |
C19—C9—C10 | 104.6 (4) | H21A—C21—H21B | 108.1 |
C8—C9—C10 | 115.5 (5) | O8—C22—C21 | 110.5 (4) |
C19—C9—H9 | 111.1 | O8—C22—H22A | 109.6 |
C8—C9—H9 | 111.1 | C21—C22—H22A | 109.6 |
C10—C9—H9 | 111.1 | O8—C22—H22B | 109.6 |
O4—C10—C9 | 105.8 (4) | C21—C22—H22B | 109.6 |
O4—C10—H10A | 110.6 | H22A—C22—H22B | 108.1 |
C9—C10—H10A | 110.6 | O8—C23—C24 | 110.0 (4) |
O4—C10—H10B | 110.6 | O8—C23—H23A | 109.7 |
C9—C10—H10B | 110.6 | C24—C23—H23A | 109.7 |
H10A—C10—H10B | 108.7 | O8—C23—H23B | 109.7 |
C16—C11—C12 | 119.8 (4) | C24—C23—H23B | 109.7 |
C16—C11—C18 | 121.7 (4) | H23A—C23—H23B | 108.2 |
C12—C11—C18 | 118.3 (4) | O7—C24—C23 | 110.4 (3) |
C13—C12—C11 | 119.8 (4) | O7—C24—H24A | 109.6 |
C13—C12—H12 | 120.1 | C23—C24—H24A | 109.6 |
C11—C12—H12 | 120.1 | O7—C24—H24B | 109.6 |
O5—C13—C12 | 124.7 (4) | C23—C24—H24B | 109.6 |
O5—C13—C14 | 115.0 (4) | H24A—C24—H24B | 108.1 |
C12—C13—C14 | 120.3 (4) | C3—O1—C7 | 116.3 (4) |
O6—C14—C15 | 119.4 (4) | C4—O2—H2A | 109.5 |
O6—C14—C13 | 121.5 (4) | C20—O3—C8 | 106.2 (3) |
C15—C14—C13 | 119.1 (4) | C10—O4—C18 | 105.1 (3) |
C14—C15—C16 | 120.9 (4) | C13—O5—C17 | 116.9 (4) |
C14—C15—H15 | 119.6 | C14—O6—H6A | 109.5 |
C16—C15—H15 | 119.6 | C24—O7—C21 | 109.4 (3) |
C11—C16—C15 | 120.1 (4) | C23—O8—C22 | 109.4 (3) |
| | | |
C6—C1—C2—C3 | 0.3 (7) | C12—C11—C16—C15 | 1.1 (7) |
C8—C1—C2—C3 | −179.1 (4) | C18—C11—C16—C15 | −174.1 (5) |
C1—C2—C3—O1 | −179.7 (4) | C14—C15—C16—C11 | −0.4 (8) |
C1—C2—C3—C4 | 0.9 (7) | C16—C11—C18—O4 | −137.8 (5) |
O1—C3—C4—O2 | 0.4 (6) | C12—C11—C18—O4 | 46.8 (6) |
C2—C3—C4—O2 | 179.9 (5) | C16—C11—C18—C19 | −17.4 (7) |
O1—C3—C4—C5 | 179.2 (4) | C12—C11—C18—C19 | 167.3 (5) |
C2—C3—C4—C5 | −1.3 (7) | C8—C9—C19—C18 | −105.5 (4) |
O2—C4—C5—C6 | 179.3 (5) | C10—C9—C19—C18 | 15.5 (5) |
C3—C4—C5—C6 | 0.4 (7) | C8—C9—C19—C20 | 15.6 (5) |
C4—C5—C6—C1 | 0.8 (8) | C10—C9—C19—C20 | 136.6 (5) |
C2—C1—C6—C5 | −1.2 (8) | O4—C18—C19—C9 | −35.8 (5) |
C8—C1—C6—C5 | 178.2 (5) | C11—C18—C19—C9 | −158.9 (4) |
C2—C1—C8—O3 | −14.4 (6) | O4—C18—C19—C20 | −149.0 (4) |
C6—C1—C8—O3 | 166.2 (5) | C11—C18—C19—C20 | 87.9 (5) |
C2—C1—C8—C9 | 103.6 (5) | C9—C19—C20—O3 | 8.3 (6) |
C6—C1—C8—C9 | −75.9 (6) | C18—C19—C20—O3 | 120.1 (5) |
O3—C8—C9—C19 | −34.7 (5) | O7—C21—C22—O8 | 58.5 (5) |
C1—C8—C9—C19 | −155.8 (4) | O8—C23—C24—O7 | −59.5 (5) |
O3—C8—C9—C10 | −148.0 (4) | C2—C3—O1—C7 | 6.5 (7) |
C1—C8—C9—C10 | 90.9 (5) | C4—C3—O1—C7 | −174.1 (5) |
C19—C9—C10—O4 | 9.2 (6) | C19—C20—O3—C8 | −31.1 (6) |
C8—C9—C10—O4 | 121.4 (5) | C9—C8—O3—C20 | 41.5 (5) |
C16—C11—C12—C13 | −0.3 (7) | C1—C8—O3—C20 | 166.8 (4) |
C18—C11—C12—C13 | 175.1 (4) | C9—C10—O4—C18 | −32.4 (6) |
C11—C12—C13—O5 | 179.4 (5) | C19—C18—O4—C10 | 43.1 (5) |
C11—C12—C13—C14 | −1.1 (7) | C11—C18—O4—C10 | 171.8 (4) |
O5—C13—C14—O6 | −0.7 (6) | C12—C13—O5—C17 | −8.3 (7) |
C12—C13—C14—O6 | 179.8 (4) | C14—C13—O5—C17 | 172.3 (5) |
O5—C13—C14—C15 | −178.7 (4) | C23—C24—O7—C21 | 58.3 (5) |
C12—C13—C14—C15 | 1.8 (7) | C22—C21—O7—C24 | −57.7 (5) |
O6—C14—C15—C16 | −179.1 (5) | C24—C23—O8—C22 | 59.1 (5) |
C13—C14—C15—C16 | −1.1 (7) | C21—C22—O8—C23 | −58.9 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O1 | 0.84 | 2.23 | 2.672 (4) | 113 |
O2—H2A···O7i | 0.84 | 1.96 | 2.720 (4) | 149 |
O6—H6A···O5 | 0.84 | 2.29 | 2.694 (4) | 110 |
O6—H6A···O8 | 0.84 | 1.95 | 2.723 (4) | 153 |
Symmetry code: (i) x+1, y, z−1. |
A comparison of torsion angles (°) in the central dioxabicyclooctane
ring system. topTorsion angle | polymorph A | polymorph B |
O3-C8-C9-C19 | -38.1 (2) | -34.7 (5) |
C8-C9-C19-C20 | 20.3 (2) | 15.6 (5) |
C9-C19-C20-O3 | 4.0 (3) | 8.3 (6) |
C19-C20-O3-C8 | -28.8 (3) | -31.1 (6) |
C20-O3-C8-C9 | 42.5 (3) | 41.5 (5) |
O4-C18-C19-C9 | -34.6 (2) | -35.8 (5) |
C18-C19-C9-C10 | 19.1 (2) | 15.5 (5) |
C19-C9-C10-O4 | 2.3 (3) | 9.2 (6) |
C9-C10-O4-C18 | -25.2 (3) | -32.4 (6) |
C10-O4-C18-C19 | 37.8 (2) | 43.1 (5) |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.