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The title compound, (I), 3β,15α,25-trihydroxy-16,23-dioxo-6α,19α-epidioxy-9,10-
seco-9,19-cyclolanost-5(10),9(11)-diene 3-
O-α-
L-arabinopyranoside, crystallizes as the monohydrate, C
35H
52O
11·H
2O. It has an
endo-epoxide rather than two OH groups on its seven-membered ring. The O—O distance is 1.473 (3) Å, and the C—O—O—C torsion angle is −30.4 (3)°. O
O distances in hydrogen bonds are in the range 2.679 (3)–3.015 (3) Å.
Supporting information
CCDC reference: 647209
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.081
- Data-to-parameter ratio = 8.7
checkCIF/PLATON results
No syntax errors found
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 26.40
From the CIF: _reflns_number_total 3870
Count of symmetry unique reflns 4009
Completeness (_total/calc) 96.53%
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 C3 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C19 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C31 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C33 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C34 = . S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
14 ALERT level G = General alerts; check
13 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
0 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
checkCIF publication errors
Alert level A
PUBL018_ALERT_1_A The author field is longer than 65 characters.
Please check that the author/address loop has been
completed according to the CIF specification.
Author = USA, National Center for Natural Products Research University of issippi University MS 38677 USA and Department of Pharmacognosy School of Pharmacy University of Mississippi University MS 38677
PUBL019_ALERT_1_A The author field is longer than 8 words.
Please check that the author/address loop has been
completed according to the CIF specification.
Author = USA, National Center for Natural Products Research University of issippi University MS 38677 USA and Department of Pharmacognosy School of Pharmacy University of Mississippi University MS 38677
2 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); 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.
3
β,15
α,25-Trihydroxy-6
α,19
α-epidioxy-
16,23-dione-9,10-seco-9,19-cyclolanost-5(10),9(11)-diene
3-O-
α-
L-arabinopyranoside
top
Crystal data top
C35H52O11·H2O | F(000) = 1440 |
Mr = 666.78 | Dx = 1.288 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3458 reflections |
a = 7.6672 (15) Å | θ = 2.5–26.3° |
b = 15.324 (3) Å | µ = 0.10 mm−1 |
c = 29.260 (6) Å | T = 100 K |
V = 3437.8 (12) Å3 | Needle, colourless |
Z = 4 | 0.42 × 0.05 × 0.05 mm |
Data collection top
Nonius KappaCCD (with Oxford Cryostream) diffractometer | 2917 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.054 |
Graphite monochromator | θmax = 26.4°, θmin = 2.7° |
ω scans with κ offsets | h = −9→9 |
11976 measured reflections | k = −18→18 |
3870 independent reflections | l = −36→36 |
Refinement top
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)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.081 | w = 1/[σ2(Fo2) + (0.0264P)2 + 0.7561P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3870 reflections | Δρmax = 0.21 e Å−3 |
443 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0019 (3) |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.5938 (2) | 0.54869 (12) | 0.55642 (6) | 0.0179 (5) | |
O2 | 0.9810 (3) | 0.72012 (14) | 0.67590 (7) | 0.0302 (6) | |
O3 | 0.8662 (3) | 0.68290 (14) | 0.71125 (7) | 0.0303 (6) | |
O4 | 1.2345 (3) | 0.38793 (15) | 0.62527 (7) | 0.0242 (5) | |
H4 | 1.2442 | 0.3911 | 0.5967 | 0.036* | |
O5 | 1.1745 (3) | 0.21578 (14) | 0.65149 (8) | 0.0350 (6) | |
O6 | 0.9700 (3) | 0.06553 (14) | 0.61060 (7) | 0.0304 (6) | |
O7 | 1.3166 (3) | 0.02478 (14) | 0.58416 (7) | 0.0345 (6) | |
H7 | 1.2196 | 0.0416 | 0.5742 | 0.052* | |
O8 | 0.3311 (2) | 0.52353 (12) | 0.52308 (6) | 0.0196 (5) | |
O9 | 0.7286 (2) | 0.39408 (13) | 0.52032 (9) | 0.0304 (6) | |
H9 | 0.7495 | 0.3405 | 0.5177 | 0.046* | |
O10 | 0.4532 (3) | 0.26318 (12) | 0.49890 (7) | 0.0217 (5) | |
H10 | 0.4394 | 0.2523 | 0.5268 | 0.033* | |
O11 | 0.1704 (3) | 0.35883 (13) | 0.53364 (6) | 0.0236 (5) | |
H11 | 0.1003 | 0.3177 | 0.5289 | 0.035* | |
C1 | 0.4852 (4) | 0.6541 (2) | 0.63134 (10) | 0.0221 (7) | |
H1A | 0.4190 | 0.6939 | 0.6516 | 0.027* | |
H1B | 0.4388 | 0.5944 | 0.6357 | 0.027* | |
C2 | 0.4585 (4) | 0.68180 (19) | 0.58176 (10) | 0.0209 (7) | |
H2A | 0.3420 | 0.6624 | 0.5712 | 0.025* | |
H2B | 0.4629 | 0.7462 | 0.5796 | 0.025* | |
C3 | 0.5978 (4) | 0.64263 (18) | 0.55121 (10) | 0.0170 (7) | |
H3 | 0.5727 | 0.6581 | 0.5187 | 0.020* | |
C4 | 0.7823 (4) | 0.67447 (19) | 0.56395 (9) | 0.0171 (7) | |
C5 | 0.8050 (4) | 0.66532 (18) | 0.61505 (9) | 0.0182 (7) | |
C6 | 0.9835 (4) | 0.6636 (2) | 0.63668 (10) | 0.0229 (7) | |
H6 | 1.0680 | 0.6885 | 0.6142 | 0.027* | |
C7 | 1.0470 (4) | 0.57050 (19) | 0.64930 (10) | 0.0214 (7) | |
H7A | 1.1186 | 0.5479 | 0.6237 | 0.026* | |
H7B | 1.1237 | 0.5748 | 0.6764 | 0.026* | |
C8 | 0.9025 (4) | 0.50382 (18) | 0.65960 (10) | 0.0173 (7) | |
H8 | 0.8370 | 0.4952 | 0.6304 | 0.021* | |
C9 | 0.7700 (4) | 0.5358 (2) | 0.69453 (9) | 0.0192 (7) | |
C10 | 0.6744 (4) | 0.65584 (18) | 0.64454 (10) | 0.0178 (7) | |
C11 | 0.6909 (4) | 0.48231 (19) | 0.72402 (10) | 0.0204 (7) | |
H11A | 0.6084 | 0.5074 | 0.7444 | 0.024* | |
C12 | 0.7217 (4) | 0.38508 (19) | 0.72761 (9) | 0.0214 (7) | |
H12A | 0.6087 | 0.3547 | 0.7315 | 0.026* | |
H12B | 0.7946 | 0.3726 | 0.7548 | 0.026* | |
C13 | 0.8127 (4) | 0.35079 (19) | 0.68487 (9) | 0.0169 (7) | |
C14 | 0.9709 (4) | 0.41340 (19) | 0.67377 (9) | 0.0167 (7) | |
C15 | 1.0648 (4) | 0.36076 (19) | 0.63658 (10) | 0.0192 (7) | |
H15 | 0.9917 | 0.3611 | 0.6083 | 0.023* | |
C16 | 1.0609 (4) | 0.2700 (2) | 0.65704 (10) | 0.0205 (7) | |
C17 | 0.9045 (4) | 0.25988 (18) | 0.68912 (10) | 0.0186 (7) | |
H17 | 0.9535 | 0.2573 | 0.7208 | 0.022* | |
C18 | 0.6780 (4) | 0.3488 (2) | 0.64580 (10) | 0.0223 (7) | |
H18A | 0.5852 | 0.3072 | 0.6533 | 0.033* | |
H18B | 0.7354 | 0.3308 | 0.6174 | 0.033* | |
H18C | 0.6276 | 0.4071 | 0.6418 | 0.033* | |
C19 | 0.7238 (4) | 0.63203 (19) | 0.69266 (10) | 0.0216 (7) | |
H19 | 0.6194 | 0.6415 | 0.7125 | 0.026* | |
C20 | 0.8014 (4) | 0.17491 (19) | 0.68247 (10) | 0.0212 (7) | |
H20 | 0.7533 | 0.1735 | 0.6507 | 0.025* | |
C21 | 0.6501 (4) | 0.1692 (2) | 0.71656 (11) | 0.0310 (8) | |
H21A | 0.5909 | 0.1129 | 0.7131 | 0.047* | |
H21B | 0.5672 | 0.2166 | 0.7106 | 0.047* | |
H21C | 0.6954 | 0.1745 | 0.7478 | 0.047* | |
C22 | 0.9189 (4) | 0.0942 (2) | 0.68969 (10) | 0.0245 (8) | |
H22A | 1.0006 | 0.1076 | 0.7149 | 0.029* | |
H22B | 0.8437 | 0.0456 | 0.7001 | 0.029* | |
C23 | 1.0250 (4) | 0.06180 (19) | 0.64969 (10) | 0.0251 (8) | |
C24 | 1.1969 (4) | 0.0197 (2) | 0.66146 (10) | 0.0259 (8) | |
H24A | 1.1770 | −0.0209 | 0.6873 | 0.031* | |
H24B | 1.2768 | 0.0659 | 0.6724 | 0.031* | |
C25 | 1.2900 (4) | −0.03084 (19) | 0.62352 (10) | 0.0258 (8) | |
C26 | 1.1852 (5) | −0.1109 (2) | 0.60965 (12) | 0.0399 (9) | |
H26A | 1.0668 | −0.0932 | 0.6011 | 0.060* | |
H26B | 1.1797 | −0.1518 | 0.6354 | 0.060* | |
H26C | 1.2415 | −0.1393 | 0.5835 | 0.060* | |
C27 | 1.4730 (4) | −0.0559 (2) | 0.63875 (12) | 0.0402 (9) | |
H27A | 1.5321 | −0.0871 | 0.6140 | 0.060* | |
H27B | 1.4658 | −0.0937 | 0.6657 | 0.060* | |
H27C | 1.5388 | −0.0031 | 0.6464 | 0.060* | |
C28 | 1.0967 (4) | 0.42256 (19) | 0.71508 (9) | 0.0202 (7) | |
H28A | 1.2090 | 0.4455 | 0.7045 | 0.030* | |
H28B | 1.1143 | 0.3653 | 0.7292 | 0.030* | |
H28C | 1.0462 | 0.4627 | 0.7375 | 0.030* | |
C29 | 0.8033 (4) | 0.77048 (19) | 0.54924 (10) | 0.0255 (8) | |
H29A | 0.7162 | 0.8064 | 0.5650 | 0.038* | |
H29B | 0.7865 | 0.7752 | 0.5161 | 0.038* | |
H29C | 0.9205 | 0.7909 | 0.5572 | 0.038* | |
C30 | 0.9160 (4) | 0.6196 (2) | 0.53750 (10) | 0.0249 (8) | |
H30A | 1.0337 | 0.6415 | 0.5437 | 0.037* | |
H30B | 0.8920 | 0.6238 | 0.5047 | 0.037* | |
H30C | 0.9076 | 0.5585 | 0.5472 | 0.037* | |
C31 | 0.5128 (4) | 0.50448 (18) | 0.52093 (10) | 0.0171 (7) | |
H31 | 0.5612 | 0.5247 | 0.4910 | 0.021* | |
C32 | 0.5458 (4) | 0.40691 (19) | 0.52657 (10) | 0.0195 (7) | |
H32 | 0.5118 | 0.3884 | 0.5581 | 0.023* | |
C33 | 0.4400 (4) | 0.35558 (18) | 0.49153 (10) | 0.0180 (7) | |
H33 | 0.4892 | 0.3685 | 0.4606 | 0.022* | |
C34 | 0.2492 (4) | 0.38399 (19) | 0.49156 (10) | 0.0196 (7) | |
H34 | 0.1866 | 0.3554 | 0.4656 | 0.023* | |
C35 | 0.2384 (4) | 0.48186 (18) | 0.48652 (10) | 0.0213 (7) | |
H35A | 0.2894 | 0.4996 | 0.4569 | 0.026* | |
H35B | 0.1147 | 0.5004 | 0.4870 | 0.026* | |
O1W | 0.4361 (3) | 0.20066 (15) | 0.58443 (8) | 0.0291 (6) | |
H1W | 0.411 (5) | 0.145 (2) | 0.5843 (12) | 0.044* | |
H2W | 0.360 (5) | 0.225 (2) | 0.6079 (11) | 0.044* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0188 (11) | 0.0131 (10) | 0.0218 (10) | −0.0007 (10) | −0.0028 (9) | −0.0004 (9) |
O2 | 0.0317 (13) | 0.0283 (12) | 0.0306 (12) | −0.0065 (12) | −0.0038 (12) | −0.0027 (11) |
O3 | 0.0361 (14) | 0.0288 (13) | 0.0261 (12) | −0.0081 (12) | −0.0007 (11) | −0.0011 (11) |
O4 | 0.0158 (11) | 0.0325 (12) | 0.0244 (11) | −0.0031 (11) | 0.0059 (10) | 0.0022 (11) |
O5 | 0.0334 (13) | 0.0234 (12) | 0.0481 (15) | 0.0073 (13) | 0.0195 (12) | −0.0010 (11) |
O6 | 0.0413 (14) | 0.0304 (13) | 0.0194 (11) | 0.0047 (12) | −0.0064 (11) | −0.0007 (10) |
O7 | 0.0472 (15) | 0.0300 (13) | 0.0261 (12) | 0.0034 (14) | −0.0034 (12) | 0.0036 (11) |
O8 | 0.0139 (10) | 0.0201 (11) | 0.0248 (11) | 0.0027 (10) | −0.0029 (9) | −0.0059 (10) |
O9 | 0.0132 (11) | 0.0182 (11) | 0.0597 (15) | 0.0038 (10) | 0.0039 (11) | −0.0044 (12) |
O10 | 0.0304 (12) | 0.0154 (11) | 0.0194 (10) | 0.0019 (10) | 0.0026 (11) | −0.0003 (9) |
O11 | 0.0197 (11) | 0.0291 (13) | 0.0220 (11) | −0.0090 (11) | 0.0050 (10) | −0.0066 (10) |
C1 | 0.0199 (16) | 0.0214 (17) | 0.0251 (17) | 0.0055 (15) | 0.0039 (14) | −0.0026 (15) |
C2 | 0.0149 (15) | 0.0171 (16) | 0.0306 (17) | 0.0016 (15) | −0.0030 (14) | 0.0001 (15) |
C3 | 0.0184 (16) | 0.0118 (15) | 0.0208 (16) | −0.0012 (14) | −0.0022 (14) | 0.0023 (13) |
C4 | 0.0137 (16) | 0.0169 (16) | 0.0207 (15) | −0.0023 (15) | −0.0009 (13) | −0.0014 (14) |
C5 | 0.0202 (16) | 0.0106 (15) | 0.0240 (16) | −0.0015 (15) | −0.0028 (14) | −0.0021 (14) |
C6 | 0.0197 (16) | 0.0250 (18) | 0.0240 (17) | −0.0009 (16) | −0.0016 (14) | −0.0055 (15) |
C7 | 0.0137 (15) | 0.0254 (17) | 0.0250 (16) | −0.0038 (16) | −0.0015 (14) | 0.0002 (14) |
C8 | 0.0172 (16) | 0.0183 (16) | 0.0165 (15) | −0.0022 (15) | −0.0012 (13) | 0.0003 (14) |
C9 | 0.0161 (16) | 0.0256 (17) | 0.0160 (15) | 0.0007 (16) | −0.0010 (13) | −0.0024 (14) |
C10 | 0.0205 (16) | 0.0117 (15) | 0.0211 (16) | −0.0012 (15) | 0.0021 (15) | −0.0018 (14) |
C11 | 0.0191 (16) | 0.0229 (17) | 0.0191 (16) | 0.0067 (16) | 0.0035 (14) | −0.0044 (14) |
C12 | 0.0199 (17) | 0.0274 (18) | 0.0167 (15) | 0.0016 (16) | 0.0021 (14) | −0.0004 (14) |
C13 | 0.0158 (15) | 0.0196 (16) | 0.0154 (15) | −0.0033 (15) | 0.0009 (14) | 0.0003 (13) |
C14 | 0.0172 (15) | 0.0218 (17) | 0.0112 (14) | −0.0035 (15) | −0.0007 (13) | −0.0009 (13) |
C15 | 0.0131 (15) | 0.0260 (18) | 0.0185 (16) | −0.0002 (15) | 0.0012 (14) | −0.0005 (14) |
C16 | 0.0181 (17) | 0.0233 (18) | 0.0201 (16) | −0.0019 (16) | 0.0003 (14) | −0.0053 (14) |
C17 | 0.0210 (16) | 0.0203 (17) | 0.0146 (15) | −0.0015 (16) | 0.0003 (14) | −0.0005 (14) |
C18 | 0.0167 (15) | 0.0262 (18) | 0.0241 (16) | −0.0020 (16) | 0.0003 (15) | 0.0006 (15) |
C19 | 0.0211 (17) | 0.0200 (17) | 0.0238 (16) | −0.0005 (16) | 0.0018 (15) | −0.0008 (14) |
C20 | 0.0269 (18) | 0.0202 (17) | 0.0164 (15) | −0.0038 (16) | 0.0017 (14) | 0.0000 (14) |
C21 | 0.0294 (19) | 0.0303 (19) | 0.0334 (19) | −0.0083 (18) | 0.0066 (16) | 0.0029 (17) |
C22 | 0.0314 (19) | 0.0210 (17) | 0.0210 (16) | −0.0040 (17) | −0.0014 (15) | 0.0060 (14) |
C23 | 0.0351 (19) | 0.0141 (16) | 0.0260 (18) | −0.0045 (17) | −0.0036 (16) | 0.0018 (15) |
C24 | 0.037 (2) | 0.0191 (17) | 0.0219 (16) | −0.0001 (17) | −0.0055 (16) | 0.0037 (14) |
C25 | 0.034 (2) | 0.0177 (16) | 0.0257 (17) | 0.0019 (16) | −0.0053 (16) | 0.0052 (14) |
C26 | 0.044 (2) | 0.0242 (19) | 0.051 (2) | −0.002 (2) | 0.000 (2) | −0.0050 (18) |
C27 | 0.040 (2) | 0.041 (2) | 0.040 (2) | 0.007 (2) | −0.0036 (18) | −0.0021 (19) |
C28 | 0.0224 (17) | 0.0190 (17) | 0.0193 (15) | 0.0002 (15) | −0.0026 (14) | −0.0005 (14) |
C29 | 0.0241 (17) | 0.0230 (17) | 0.0294 (18) | −0.0057 (16) | −0.0011 (16) | 0.0056 (15) |
C30 | 0.0193 (16) | 0.0292 (18) | 0.0262 (17) | 0.0000 (16) | 0.0039 (15) | −0.0013 (15) |
C31 | 0.0169 (15) | 0.0177 (16) | 0.0167 (15) | −0.0004 (14) | 0.0020 (13) | −0.0014 (14) |
C32 | 0.0114 (15) | 0.0220 (17) | 0.0249 (16) | 0.0029 (14) | 0.0040 (14) | 0.0006 (15) |
C33 | 0.0214 (16) | 0.0136 (15) | 0.0190 (15) | 0.0011 (15) | 0.0037 (14) | 0.0027 (13) |
C34 | 0.0211 (16) | 0.0221 (17) | 0.0155 (15) | −0.0002 (15) | 0.0020 (14) | −0.0025 (14) |
C35 | 0.0185 (16) | 0.0250 (17) | 0.0204 (16) | 0.0046 (15) | −0.0049 (14) | −0.0057 (14) |
O1W | 0.0323 (14) | 0.0260 (13) | 0.0291 (12) | 0.0003 (12) | 0.0090 (11) | −0.0007 (11) |
Geometric parameters (Å, º) top
O1—C31 | 1.387 (3) | C14—C28 | 1.553 (4) |
O1—C3 | 1.448 (3) | C15—C16 | 1.514 (4) |
O2—C6 | 1.438 (3) | C15—H15 | 1.0000 |
O2—O3 | 1.473 (3) | C16—C17 | 1.530 (4) |
O3—C19 | 1.447 (4) | C17—C20 | 1.536 (4) |
O4—C15 | 1.406 (3) | C17—H17 | 1.0000 |
O4—H4 | 0.8400 | C18—H18A | 0.9800 |
O5—C16 | 1.215 (3) | C18—H18B | 0.9800 |
O6—C23 | 1.220 (3) | C18—H18C | 0.9800 |
O7—C25 | 1.447 (3) | C19—H19 | 1.0000 |
O7—H7 | 0.8400 | C20—C21 | 1.532 (4) |
O8—C31 | 1.425 (3) | C20—C22 | 1.544 (4) |
O8—C35 | 1.434 (3) | C20—H20 | 1.0000 |
O9—C32 | 1.427 (3) | C21—H21A | 0.9800 |
O9—H9 | 0.8400 | C21—H21B | 0.9800 |
O10—C33 | 1.436 (3) | C21—H21C | 0.9800 |
O10—H10 | 0.8400 | C22—C23 | 1.510 (4) |
O11—C34 | 1.424 (3) | C22—H22A | 0.9900 |
O11—H11 | 0.8400 | C22—H22B | 0.9900 |
C1—C10 | 1.502 (4) | C23—C24 | 1.508 (4) |
C1—C2 | 1.525 (4) | C24—C25 | 1.530 (4) |
C1—H1A | 0.9900 | C24—H24A | 0.9900 |
C1—H1B | 0.9900 | C24—H24B | 0.9900 |
C2—C3 | 1.517 (4) | C25—C27 | 1.521 (5) |
C2—H2A | 0.9900 | C25—C26 | 1.522 (5) |
C2—H2B | 0.9900 | C26—H26A | 0.9800 |
C3—C4 | 1.542 (4) | C26—H26B | 0.9800 |
C3—H3 | 1.0000 | C26—H26C | 0.9800 |
C4—C5 | 1.512 (4) | C27—H27A | 0.9800 |
C4—C30 | 1.535 (4) | C27—H27B | 0.9800 |
C4—C29 | 1.541 (4) | C27—H27C | 0.9800 |
C5—C10 | 1.330 (4) | C28—H28A | 0.9800 |
C5—C6 | 1.508 (4) | C28—H28B | 0.9800 |
C6—C7 | 1.552 (4) | C28—H28C | 0.9800 |
C6—H6 | 1.0000 | C29—H29A | 0.9800 |
C7—C8 | 1.537 (4) | C29—H29B | 0.9800 |
C7—H7A | 0.9900 | C29—H29C | 0.9800 |
C7—H7B | 0.9900 | C30—H30A | 0.9800 |
C8—C9 | 1.522 (4) | C30—H30B | 0.9800 |
C8—C14 | 1.539 (4) | C30—H30C | 0.9800 |
C8—H8 | 1.0000 | C31—C32 | 1.525 (4) |
C9—C11 | 1.336 (4) | C31—H31 | 1.0000 |
C9—C19 | 1.517 (4) | C32—C33 | 1.526 (4) |
C10—C19 | 1.503 (4) | C32—H32 | 1.0000 |
C11—C12 | 1.512 (4) | C33—C34 | 1.526 (4) |
C11—H11A | 0.9500 | C33—H33 | 1.0000 |
C12—C13 | 1.525 (4) | C34—C35 | 1.509 (4) |
C12—H12A | 0.9900 | C34—H34 | 1.0000 |
C12—H12B | 0.9900 | C35—H35A | 0.9900 |
C13—C18 | 1.541 (4) | C35—H35B | 0.9900 |
C13—C17 | 1.566 (4) | O1W—H1W | 0.87 (3) |
C13—C14 | 1.580 (4) | O1W—H2W | 0.97 (4) |
C14—C15 | 1.534 (4) | | |
| | | |
C31—O1—C3 | 114.6 (2) | H18B—C18—H18C | 109.5 |
C6—O2—O3 | 109.6 (2) | O3—C19—C10 | 114.3 (2) |
C19—O3—O2 | 113.29 (19) | O3—C19—C9 | 109.5 (2) |
C15—O4—H4 | 109.5 | C10—C19—C9 | 109.2 (2) |
C25—O7—H7 | 109.5 | O3—C19—H19 | 107.9 |
C31—O8—C35 | 111.1 (2) | C10—C19—H19 | 107.9 |
C32—O9—H9 | 109.5 | C9—C19—H19 | 107.9 |
C33—O10—H10 | 109.5 | C21—C20—C17 | 110.8 (2) |
C34—O11—H11 | 109.5 | C21—C20—C22 | 107.9 (2) |
C10—C1—C2 | 111.7 (2) | C17—C20—C22 | 111.2 (2) |
C10—C1—H1A | 109.3 | C21—C20—H20 | 109.0 |
C2—C1—H1A | 109.3 | C17—C20—H20 | 109.0 |
C10—C1—H1B | 109.3 | C22—C20—H20 | 109.0 |
C2—C1—H1B | 109.3 | C20—C21—H21A | 109.5 |
H1A—C1—H1B | 107.9 | C20—C21—H21B | 109.5 |
C3—C2—C1 | 110.9 (2) | H21A—C21—H21B | 109.5 |
C3—C2—H2A | 109.5 | C20—C21—H21C | 109.5 |
C1—C2—H2A | 109.5 | H21A—C21—H21C | 109.5 |
C3—C2—H2B | 109.5 | H21B—C21—H21C | 109.5 |
C1—C2—H2B | 109.5 | C23—C22—C20 | 118.2 (2) |
H2A—C2—H2B | 108.1 | C23—C22—H22A | 107.8 |
O1—C3—C2 | 108.4 (2) | C20—C22—H22A | 107.8 |
O1—C3—C4 | 108.0 (2) | C23—C22—H22B | 107.8 |
C2—C3—C4 | 112.2 (2) | C20—C22—H22B | 107.8 |
O1—C3—H3 | 109.4 | H22A—C22—H22B | 107.1 |
C2—C3—H3 | 109.4 | O6—C23—C24 | 122.4 (3) |
C4—C3—H3 | 109.4 | O6—C23—C22 | 121.7 (3) |
C5—C4—C30 | 111.8 (2) | C24—C23—C22 | 115.8 (3) |
C5—C4—C29 | 110.7 (2) | C23—C24—C25 | 117.3 (3) |
C30—C4—C29 | 108.2 (2) | C23—C24—H24A | 108.0 |
C5—C4—C3 | 108.4 (2) | C25—C24—H24A | 108.0 |
C30—C4—C3 | 108.5 (2) | C23—C24—H24B | 108.0 |
C29—C4—C3 | 109.3 (2) | C25—C24—H24B | 108.0 |
C10—C5—C6 | 114.2 (2) | H24A—C24—H24B | 107.2 |
C10—C5—C4 | 124.4 (3) | O7—C25—C27 | 104.6 (3) |
C6—C5—C4 | 121.4 (3) | O7—C25—C26 | 109.7 (2) |
O2—C6—C5 | 108.2 (2) | C27—C25—C26 | 111.2 (3) |
O2—C6—C7 | 111.6 (2) | O7—C25—C24 | 110.2 (2) |
C5—C6—C7 | 113.6 (3) | C27—C25—C24 | 110.2 (3) |
O2—C6—H6 | 107.7 | C26—C25—C24 | 110.8 (3) |
C5—C6—H6 | 107.7 | C25—C26—H26A | 109.5 |
C7—C6—H6 | 107.7 | C25—C26—H26B | 109.5 |
C8—C7—C6 | 115.6 (2) | H26A—C26—H26B | 109.5 |
C8—C7—H7A | 108.4 | C25—C26—H26C | 109.5 |
C6—C7—H7A | 108.4 | H26A—C26—H26C | 109.5 |
C8—C7—H7B | 108.4 | H26B—C26—H26C | 109.5 |
C6—C7—H7B | 108.4 | C25—C27—H27A | 109.5 |
H7A—C7—H7B | 107.4 | C25—C27—H27B | 109.5 |
C9—C8—C7 | 113.5 (2) | H27A—C27—H27B | 109.5 |
C9—C8—C14 | 109.7 (2) | C25—C27—H27C | 109.5 |
C7—C8—C14 | 113.9 (2) | H27A—C27—H27C | 109.5 |
C9—C8—H8 | 106.4 | H27B—C27—H27C | 109.5 |
C7—C8—H8 | 106.4 | C14—C28—H28A | 109.5 |
C14—C8—H8 | 106.4 | C14—C28—H28B | 109.5 |
C11—C9—C19 | 120.9 (3) | H28A—C28—H28B | 109.5 |
C11—C9—C8 | 122.6 (3) | C14—C28—H28C | 109.5 |
C19—C9—C8 | 116.4 (3) | H28A—C28—H28C | 109.5 |
C5—C10—C1 | 124.2 (3) | H28B—C28—H28C | 109.5 |
C5—C10—C19 | 116.4 (3) | C4—C29—H29A | 109.5 |
C1—C10—C19 | 118.7 (3) | C4—C29—H29B | 109.5 |
C9—C11—C12 | 125.3 (3) | H29A—C29—H29B | 109.5 |
C9—C11—H11A | 117.3 | C4—C29—H29C | 109.5 |
C12—C11—H11A | 117.3 | H29A—C29—H29C | 109.5 |
C11—C12—C13 | 110.7 (2) | H29B—C29—H29C | 109.5 |
C11—C12—H12A | 109.5 | C4—C30—H30A | 109.5 |
C13—C12—H12A | 109.5 | C4—C30—H30B | 109.5 |
C11—C12—H12B | 109.5 | H30A—C30—H30B | 109.5 |
C13—C12—H12B | 109.5 | C4—C30—H30C | 109.5 |
H12A—C12—H12B | 108.1 | H30A—C30—H30C | 109.5 |
C12—C13—C18 | 108.0 (2) | H30B—C30—H30C | 109.5 |
C12—C13—C17 | 116.5 (2) | O1—C31—O8 | 107.7 (2) |
C18—C13—C17 | 110.0 (2) | O1—C31—C32 | 108.9 (2) |
C12—C13—C14 | 108.1 (2) | O8—C31—C32 | 111.0 (2) |
C18—C13—C14 | 112.0 (2) | O1—C31—H31 | 109.7 |
C17—C13—C14 | 102.2 (2) | O8—C31—H31 | 109.7 |
C15—C14—C8 | 116.3 (2) | C32—C31—H31 | 109.7 |
C15—C14—C28 | 108.0 (2) | O9—C32—C31 | 106.5 (2) |
C8—C14—C28 | 109.9 (2) | O9—C32—C33 | 111.4 (2) |
C15—C14—C13 | 100.8 (2) | C31—C32—C33 | 110.2 (2) |
C8—C14—C13 | 109.9 (2) | O9—C32—H32 | 109.6 |
C28—C14—C13 | 111.8 (2) | C31—C32—H32 | 109.6 |
O4—C15—C16 | 112.5 (2) | C33—C32—H32 | 109.6 |
O4—C15—C14 | 116.5 (2) | O10—C33—C32 | 111.7 (2) |
C16—C15—C14 | 101.1 (2) | O10—C33—C34 | 110.4 (2) |
O4—C15—H15 | 108.8 | C32—C33—C34 | 111.2 (2) |
C16—C15—H15 | 108.8 | O10—C33—H33 | 107.8 |
C14—C15—H15 | 108.8 | C32—C33—H33 | 107.8 |
O5—C16—C15 | 124.1 (3) | C34—C33—H33 | 107.8 |
O5—C16—C17 | 125.0 (3) | O11—C34—C35 | 109.3 (2) |
C15—C16—C17 | 110.6 (3) | O11—C34—C33 | 109.2 (2) |
C16—C17—C20 | 114.3 (2) | C35—C34—C33 | 109.6 (3) |
C16—C17—C13 | 102.3 (2) | O11—C34—H34 | 109.6 |
C20—C17—C13 | 120.8 (2) | C35—C34—H34 | 109.6 |
C16—C17—H17 | 106.1 | C33—C34—H34 | 109.6 |
C20—C17—H17 | 106.1 | O8—C35—C34 | 110.0 (2) |
C13—C17—H17 | 106.1 | O8—C35—H35A | 109.7 |
C13—C18—H18A | 109.5 | C34—C35—H35A | 109.7 |
C13—C18—H18B | 109.5 | O8—C35—H35B | 109.7 |
H18A—C18—H18B | 109.5 | C34—C35—H35B | 109.7 |
C13—C18—H18C | 109.5 | H35A—C35—H35B | 108.2 |
H18A—C18—H18C | 109.5 | H1W—O1W—H2W | 104 (3) |
| | | |
C6—O2—O3—C19 | −30.4 (3) | C13—C14—C15—O4 | −166.6 (2) |
C10—C1—C2—C3 | 41.2 (3) | C8—C14—C15—C16 | −163.0 (2) |
C31—O1—C3—C2 | 102.6 (3) | C28—C14—C15—C16 | 73.1 (3) |
C31—O1—C3—C4 | −135.6 (2) | C13—C14—C15—C16 | −44.3 (3) |
C1—C2—C3—O1 | 56.7 (3) | O4—C15—C16—O5 | −22.2 (4) |
C1—C2—C3—C4 | −62.5 (3) | C14—C15—C16—O5 | −147.2 (3) |
O1—C3—C4—C5 | −71.2 (3) | O4—C15—C16—C17 | 152.2 (2) |
C2—C3—C4—C5 | 48.3 (3) | C14—C15—C16—C17 | 27.2 (3) |
O1—C3—C4—C30 | 50.4 (3) | O5—C16—C17—C20 | −51.6 (4) |
C2—C3—C4—C30 | 169.9 (2) | C15—C16—C17—C20 | 134.1 (3) |
O1—C3—C4—C29 | 168.2 (2) | O5—C16—C17—C13 | 176.0 (3) |
C2—C3—C4—C29 | −72.4 (3) | C15—C16—C17—C13 | 1.7 (3) |
C30—C4—C5—C10 | −137.0 (3) | C12—C13—C17—C16 | −146.8 (2) |
C29—C4—C5—C10 | 102.3 (3) | C18—C13—C17—C16 | 90.0 (3) |
C3—C4—C5—C10 | −17.5 (4) | C14—C13—C17—C16 | −29.2 (3) |
C30—C4—C5—C6 | 41.1 (4) | C12—C13—C17—C20 | 84.9 (3) |
C29—C4—C5—C6 | −79.6 (3) | C18—C13—C17—C20 | −38.4 (3) |
C3—C4—C5—C6 | 160.6 (3) | C14—C13—C17—C20 | −157.5 (2) |
O3—O2—C6—C5 | 67.3 (3) | O2—O3—C19—C10 | −24.2 (3) |
O3—O2—C6—C7 | −58.4 (3) | O2—O3—C19—C9 | 98.6 (3) |
C10—C5—C6—O2 | −47.1 (3) | C5—C10—C19—O3 | 46.1 (3) |
C4—C5—C6—O2 | 134.6 (3) | C1—C10—C19—O3 | −142.8 (3) |
C10—C5—C6—C7 | 77.4 (3) | C5—C10—C19—C9 | −76.9 (3) |
C4—C5—C6—C7 | −100.9 (3) | C1—C10—C19—C9 | 94.2 (3) |
O2—C6—C7—C8 | 95.1 (3) | C11—C9—C19—O3 | 108.7 (3) |
C5—C6—C7—C8 | −27.5 (4) | C8—C9—C19—O3 | −74.5 (3) |
C6—C7—C8—C9 | −51.3 (3) | C11—C9—C19—C10 | −125.5 (3) |
C6—C7—C8—C14 | −177.8 (2) | C8—C9—C19—C10 | 51.3 (3) |
C7—C8—C9—C11 | −146.9 (3) | C16—C17—C20—C21 | 178.8 (3) |
C14—C8—C9—C11 | −18.2 (4) | C13—C17—C20—C21 | −58.4 (3) |
C7—C8—C9—C19 | 36.3 (3) | C16—C17—C20—C22 | 58.8 (3) |
C14—C8—C9—C19 | 165.0 (2) | C13—C17—C20—C22 | −178.4 (2) |
C6—C5—C10—C1 | −179.2 (3) | C21—C20—C22—C23 | 153.2 (3) |
C4—C5—C10—C1 | −0.9 (5) | C17—C20—C22—C23 | −85.1 (3) |
C6—C5—C10—C19 | −8.7 (4) | C20—C22—C23—O6 | −34.9 (4) |
C4—C5—C10—C19 | 169.6 (3) | C20—C22—C23—C24 | 148.8 (3) |
C2—C1—C10—C5 | −10.9 (4) | O6—C23—C24—C25 | −8.8 (4) |
C2—C1—C10—C19 | 178.8 (2) | C22—C23—C24—C25 | 167.5 (3) |
C19—C9—C11—C12 | 177.6 (3) | C23—C24—C25—O7 | 55.8 (4) |
C8—C9—C11—C12 | 1.0 (5) | C23—C24—C25—C27 | 170.7 (3) |
C9—C11—C12—C13 | −16.7 (4) | C23—C24—C25—C26 | −65.8 (3) |
C11—C12—C13—C18 | −74.0 (3) | C3—O1—C31—O8 | −69.4 (3) |
C11—C12—C13—C17 | 161.7 (2) | C3—O1—C31—C32 | 170.2 (2) |
C11—C12—C13—C14 | 47.4 (3) | C35—O8—C31—O1 | 178.4 (2) |
C9—C8—C14—C15 | 163.6 (2) | C35—O8—C31—C32 | −62.5 (3) |
C7—C8—C14—C15 | −68.0 (3) | O1—C31—C32—O9 | −66.0 (3) |
C9—C8—C14—C28 | −73.5 (3) | O8—C31—C32—O9 | 175.5 (2) |
C7—C8—C14—C28 | 55.0 (3) | O1—C31—C32—C33 | 173.0 (2) |
C9—C8—C14—C13 | 50.0 (3) | O8—C31—C32—C33 | 54.6 (3) |
C7—C8—C14—C13 | 178.4 (2) | O9—C32—C33—O10 | 68.2 (3) |
C12—C13—C14—C15 | 169.9 (2) | C31—C32—C33—O10 | −173.8 (2) |
C18—C13—C14—C15 | −71.3 (3) | O9—C32—C33—C34 | −167.9 (2) |
C17—C13—C14—C15 | 46.4 (2) | C31—C32—C33—C34 | −49.9 (3) |
C12—C13—C14—C8 | −66.9 (3) | O10—C33—C34—O11 | 57.0 (3) |
C18—C13—C14—C8 | 51.9 (3) | C32—C33—C34—O11 | −67.6 (3) |
C17—C13—C14—C8 | 169.6 (2) | O10—C33—C34—C35 | 176.7 (2) |
C12—C13—C14—C28 | 55.4 (3) | C32—C33—C34—C35 | 52.1 (3) |
C18—C13—C14—C28 | 174.2 (2) | C31—O8—C35—C34 | 64.6 (3) |
C17—C13—C14—C28 | −68.0 (3) | O11—C34—C35—O8 | 61.2 (3) |
C8—C14—C15—O4 | 74.7 (3) | C33—C34—C35—O8 | −58.5 (3) |
C28—C14—C15—O4 | −49.2 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O11i | 0.84 | 1.99 | 2.762 (3) | 152 |
O7—H7···O6 | 0.84 | 2.22 | 2.838 (3) | 130 |
O9—H9···O10ii | 0.84 | 2.28 | 3.015 (3) | 146 |
O10—H10···O1W | 0.84 | 1.86 | 2.683 (3) | 165 |
O11—H11···O10iii | 0.84 | 1.86 | 2.679 (3) | 163 |
O1W—H2W···O5iv | 0.97 (4) | 1.92 (4) | 2.815 (3) | 153 (3) |
O1W—H1W···O7iv | 0.87 (3) | 1.99 (3) | 2.847 (3) | 171 (3) |
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1/2, −z+1; (iii) x−1/2, −y+1/2, −z+1; (iv) x−1, y, z. |
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