The title compound, (
E)-3-{2-[3-(2,6-dimethoxyphenyl)-6a,10
b-dimethyl-8-methylene-decahydro-1
H-naphtho[2,1-
d][1,3]dioxin-7-yl]ethylidene}-4-hydroxy-4,5-dihydrofuran-2(3
H)-one, C
29H
38O
7, an andrographolide analogue, was semi-synthesized from andrographolide. The structure contains three fused six-membered rings adopting chair conformations and a five-membered ring adopting a twisted conformation. Intermolecular O—H
O hydrogen bonds link the molecules into chains along the
a axis which are interlinked
via C—H
π interactions.
Supporting information
CCDC reference: 629630
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.116
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.56 Ratio
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 33.51
From the CIF: _reflns_number_total 5470
Count of symmetry unique reflns 5491
Completeness (_total/calc) 99.62%
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 C4 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16 = . R
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
8 ALERT level G = General alerts; check
7 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
1 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
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
| Author Response: H.K. Fun and I.A. Razak are supervisors
of Shea-Lin Ng whereas J. Stanslas is supervisor
of S. R. Sagineedu and N. H. Lajis in this collaborative
pulication. UPM is involved in the extraction and synthesis
of the title compound and USM is involved in the structure
determination. All parties are involved in writing up the
manuscript.
|
1 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: 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).
(
E)-3-{2-[3-(2,6-dimethoxyphenyl)-6a,10
b-dimethyl-8-methylene-decahydro-
1
H-naphtho[2,1-
d][1,3]dioxin-7-yl]ethylidene}-4-hydroxy-4,5-dihydrofuran- 2(3
H)-one
top
Crystal data top
C29H38O7 | F(000) = 1072 |
Mr = 498.59 | Dx = 1.330 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 9044 reflections |
a = 6.5021 (1) Å | θ = 1.4–33.5° |
b = 12.9728 (2) Å | µ = 0.09 mm−1 |
c = 29.5163 (4) Å | T = 100 K |
V = 2489.71 (6) Å3 | Block, colourless |
Z = 4 | 0.37 × 0.26 × 0.21 mm |
Data collection top
Bruker SMART APEXII CCD area-detector diffractometer | 5470 independent reflections |
Radiation source: fine-focus sealed tube | 4724 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
Detector resolution: 8.33 pixels mm-1 | θmax = 33.5°, θmin = 1.4° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −20→19 |
Tmin = 0.873, Tmax = 0.981 | l = −43→45 |
44842 measured reflections | |
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) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0567P)2 + 0.437P] where P = (Fo2 + 2Fc2)/3 |
5470 reflections | (Δ/σ)max = 0.001 |
333 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Special details top
Experimental. The data were collected with the Oxford Cyrosystem Cobra low-temperature
attachment |
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 | 0.2961 (2) | 0.00552 (10) | 0.13187 (4) | 0.0190 (2) | |
O2 | 0.05890 (18) | −0.11704 (10) | 0.10508 (4) | 0.0180 (2) | |
O3 | −0.75262 (19) | −0.23661 (10) | 0.44792 (4) | 0.0203 (2) | |
O4 | −0.91111 (19) | −0.13808 (11) | 0.39653 (5) | 0.0232 (3) | |
O5 | −0.2838 (2) | −0.17083 (12) | 0.44088 (5) | 0.0239 (3) | |
O6 | 0.2271 (2) | 0.04408 (10) | 0.04040 (4) | 0.0211 (3) | |
O7 | 0.5386 (2) | −0.25688 (10) | 0.10018 (4) | 0.0216 (3) | |
C1 | −0.3146 (3) | 0.03003 (14) | 0.30344 (6) | 0.0188 (3) | |
C2 | −0.3396 (3) | 0.11765 (14) | 0.27032 (6) | 0.0221 (3) | |
H2A | −0.3273 | 0.1829 | 0.2861 | 0.027* | |
H2B | −0.4749 | 0.1145 | 0.2566 | 0.027* | |
C3 | −0.1739 (3) | 0.11012 (13) | 0.23350 (6) | 0.0207 (3) | |
H3A | −0.0395 | 0.1203 | 0.2470 | 0.025* | |
H3B | −0.1954 | 0.1641 | 0.2113 | 0.025* | |
C4 | −0.1804 (3) | 0.00477 (12) | 0.20994 (5) | 0.0154 (3) | |
H4A | −0.3218 | −0.0010 | 0.1987 | 0.018* | |
C5 | −0.0455 (3) | −0.00013 (13) | 0.16631 (5) | 0.0156 (3) | |
C6 | 0.1867 (3) | 0.01703 (14) | 0.17365 (6) | 0.0179 (3) | |
H6A | 0.2096 | 0.0857 | 0.1857 | 0.021* | |
H6B | 0.2379 | −0.0324 | 0.1956 | 0.021* | |
C7 | 0.2687 (2) | −0.09577 (13) | 0.11437 (6) | 0.0171 (3) | |
H7A | 0.3206 | −0.1460 | 0.1364 | 0.021* | |
C8 | −0.0728 (2) | −0.10685 (13) | 0.14421 (5) | 0.0164 (3) | |
H8A | −0.2146 | −0.1099 | 0.1331 | 0.020* | |
C9 | −0.0468 (3) | −0.19657 (13) | 0.17701 (6) | 0.0186 (3) | |
H9A | 0.0940 | −0.1984 | 0.1878 | 0.022* | |
H9B | −0.0741 | −0.2608 | 0.1613 | 0.022* | |
C10 | −0.1930 (3) | −0.18636 (12) | 0.21728 (6) | 0.0176 (3) | |
H10A | −0.1740 | −0.2449 | 0.2373 | 0.021* | |
H10B | −0.3337 | −0.1879 | 0.2064 | 0.021* | |
C11 | −0.1584 (2) | −0.08632 (12) | 0.24422 (5) | 0.0145 (3) | |
C12 | −0.3308 (2) | −0.07453 (13) | 0.28083 (6) | 0.0159 (3) | |
H12A | −0.4615 | −0.0743 | 0.2643 | 0.019* | |
C13 | −0.3444 (3) | −0.16423 (14) | 0.31478 (6) | 0.0183 (3) | |
H13A | −0.3468 | −0.2290 | 0.2983 | 0.022* | |
H13B | −0.2232 | −0.1639 | 0.3339 | 0.022* | |
C14 | −0.5323 (3) | −0.15662 (13) | 0.34375 (6) | 0.0175 (3) | |
H14A | −0.6450 | −0.1233 | 0.3311 | 0.021* | |
C15 | −0.5564 (2) | −0.19234 (13) | 0.38577 (6) | 0.0160 (3) | |
C16 | −0.4091 (3) | −0.24461 (14) | 0.41797 (6) | 0.0177 (3) | |
H16A | −0.3262 | −0.2973 | 0.4027 | 0.021* | |
C17 | −0.5579 (3) | −0.29206 (14) | 0.45230 (6) | 0.0200 (3) | |
H17A | −0.5775 | −0.3648 | 0.4460 | 0.024* | |
H17B | −0.5040 | −0.2849 | 0.4828 | 0.024* | |
C18 | −0.7570 (3) | −0.18425 (13) | 0.40881 (6) | 0.0178 (3) | |
C19 | 0.3862 (3) | −0.10678 (14) | 0.07061 (6) | 0.0177 (3) | |
C20 | 0.3590 (3) | −0.03773 (13) | 0.03481 (6) | 0.0181 (3) | |
C21 | 0.4698 (3) | −0.04796 (15) | −0.00551 (6) | 0.0212 (3) | |
H21A | 0.4535 | −0.0004 | −0.0288 | 0.025* | |
C22 | 0.6045 (3) | −0.13018 (15) | −0.01028 (6) | 0.0228 (3) | |
H22A | 0.6781 | −0.1375 | −0.0371 | 0.027* | |
C23 | 0.6316 (3) | −0.20181 (15) | 0.02417 (6) | 0.0216 (3) | |
H23A | 0.7211 | −0.2570 | 0.0204 | 0.026* | |
C24 | 0.5226 (3) | −0.18967 (14) | 0.06447 (6) | 0.0185 (3) | |
C25 | −0.1214 (3) | 0.08112 (15) | 0.13246 (6) | 0.0228 (3) | |
H25A | −0.0598 | 0.0688 | 0.1034 | 0.034* | |
H25B | −0.0837 | 0.1485 | 0.1430 | 0.034* | |
H25C | −0.2684 | 0.0768 | 0.1298 | 0.034* | |
C26 | 0.0504 (3) | −0.09003 (14) | 0.26891 (6) | 0.0193 (3) | |
H26A | 0.0379 | −0.1313 | 0.2958 | 0.029* | |
H26B | 0.0912 | −0.0214 | 0.2771 | 0.029* | |
H26C | 0.1521 | −0.1197 | 0.2493 | 0.029* | |
C27 | −0.2686 (3) | 0.04575 (15) | 0.34674 (6) | 0.0255 (4) | |
H27A | −0.2630 | 0.1210 | 0.3576 | 0.031* | |
H27B | −0.2540 | −0.0114 | 0.3677 | 0.031* | |
C28 | 0.0497 (3) | 0.04028 (16) | 0.01169 (7) | 0.0268 (4) | |
H28A | −0.0326 | 0.1007 | 0.0165 | 0.040* | |
H28B | −0.0297 | −0.0200 | 0.0187 | 0.040* | |
H28C | 0.0926 | 0.0376 | −0.0194 | 0.040* | |
C29 | 0.6697 (3) | −0.34415 (15) | 0.09405 (7) | 0.0261 (4) | |
H29A | 0.6690 | −0.3854 | 0.1211 | 0.039* | |
H29B | 0.8073 | −0.3212 | 0.0880 | 0.039* | |
H29C | 0.6209 | −0.3846 | 0.0690 | 0.039* | |
H5A | −0.166 (6) | −0.160 (3) | 0.4243 (10) | 0.064 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0177 (5) | 0.0214 (6) | 0.0180 (6) | −0.0041 (5) | 0.0030 (4) | −0.0028 (5) |
O2 | 0.0148 (5) | 0.0232 (6) | 0.0160 (5) | −0.0036 (4) | 0.0013 (4) | −0.0023 (5) |
O3 | 0.0146 (5) | 0.0284 (6) | 0.0179 (5) | 0.0001 (5) | 0.0015 (5) | 0.0040 (5) |
O4 | 0.0139 (5) | 0.0298 (7) | 0.0258 (7) | 0.0017 (5) | 0.0013 (5) | 0.0047 (5) |
O5 | 0.0142 (5) | 0.0381 (7) | 0.0194 (6) | −0.0055 (5) | 0.0006 (5) | −0.0043 (5) |
O6 | 0.0200 (6) | 0.0230 (6) | 0.0204 (6) | 0.0012 (5) | −0.0027 (5) | −0.0014 (5) |
O7 | 0.0228 (6) | 0.0206 (6) | 0.0215 (6) | 0.0036 (5) | 0.0029 (5) | 0.0013 (5) |
C1 | 0.0157 (7) | 0.0203 (8) | 0.0205 (8) | −0.0003 (6) | 0.0036 (6) | −0.0011 (6) |
C2 | 0.0243 (8) | 0.0174 (7) | 0.0248 (9) | 0.0014 (6) | 0.0048 (7) | −0.0013 (6) |
C3 | 0.0239 (8) | 0.0158 (7) | 0.0225 (8) | −0.0014 (6) | 0.0036 (6) | −0.0013 (6) |
C4 | 0.0144 (6) | 0.0153 (7) | 0.0166 (7) | 0.0008 (5) | 0.0010 (5) | 0.0005 (5) |
C5 | 0.0148 (6) | 0.0163 (7) | 0.0157 (7) | −0.0004 (6) | 0.0000 (5) | 0.0018 (5) |
C6 | 0.0170 (7) | 0.0203 (7) | 0.0164 (7) | −0.0037 (6) | 0.0017 (6) | −0.0028 (6) |
C7 | 0.0144 (6) | 0.0189 (7) | 0.0180 (7) | −0.0009 (6) | −0.0003 (6) | −0.0007 (6) |
C8 | 0.0139 (6) | 0.0208 (7) | 0.0144 (7) | −0.0018 (5) | 0.0005 (5) | −0.0003 (6) |
C9 | 0.0205 (7) | 0.0168 (7) | 0.0184 (7) | −0.0005 (6) | 0.0034 (6) | −0.0008 (6) |
C10 | 0.0173 (7) | 0.0172 (7) | 0.0181 (7) | −0.0013 (6) | 0.0018 (6) | 0.0001 (6) |
C11 | 0.0123 (6) | 0.0157 (7) | 0.0156 (7) | 0.0004 (5) | −0.0002 (5) | 0.0008 (5) |
C12 | 0.0129 (6) | 0.0180 (7) | 0.0167 (7) | 0.0002 (5) | 0.0009 (5) | 0.0021 (6) |
C13 | 0.0154 (7) | 0.0216 (7) | 0.0179 (7) | 0.0002 (6) | 0.0020 (6) | 0.0027 (6) |
C14 | 0.0132 (6) | 0.0210 (7) | 0.0184 (7) | −0.0012 (6) | 0.0002 (6) | 0.0013 (6) |
C15 | 0.0117 (6) | 0.0188 (7) | 0.0175 (7) | −0.0012 (5) | 0.0004 (5) | −0.0001 (6) |
C16 | 0.0152 (7) | 0.0231 (8) | 0.0149 (7) | 0.0010 (6) | 0.0002 (5) | −0.0006 (6) |
C17 | 0.0159 (7) | 0.0260 (8) | 0.0180 (8) | 0.0003 (6) | −0.0008 (6) | 0.0047 (6) |
C18 | 0.0146 (7) | 0.0218 (8) | 0.0171 (7) | −0.0018 (6) | 0.0005 (6) | −0.0003 (6) |
C19 | 0.0149 (6) | 0.0225 (8) | 0.0158 (7) | −0.0019 (6) | 0.0001 (5) | −0.0008 (6) |
C20 | 0.0150 (7) | 0.0198 (7) | 0.0197 (8) | −0.0025 (6) | −0.0011 (6) | −0.0015 (6) |
C21 | 0.0204 (8) | 0.0263 (8) | 0.0169 (7) | −0.0040 (7) | 0.0005 (6) | 0.0018 (6) |
C22 | 0.0172 (7) | 0.0322 (9) | 0.0190 (8) | −0.0025 (7) | 0.0031 (6) | −0.0030 (7) |
C23 | 0.0171 (7) | 0.0265 (8) | 0.0213 (8) | −0.0001 (6) | 0.0020 (6) | −0.0027 (7) |
C24 | 0.0157 (7) | 0.0217 (8) | 0.0182 (7) | −0.0018 (6) | −0.0003 (6) | −0.0003 (6) |
C25 | 0.0235 (8) | 0.0246 (8) | 0.0203 (8) | 0.0033 (7) | 0.0017 (7) | 0.0067 (7) |
C26 | 0.0137 (6) | 0.0265 (8) | 0.0177 (7) | −0.0002 (6) | −0.0006 (6) | 0.0027 (6) |
C27 | 0.0282 (9) | 0.0255 (9) | 0.0227 (9) | −0.0035 (7) | 0.0040 (7) | −0.0036 (7) |
C28 | 0.0236 (8) | 0.0321 (10) | 0.0248 (9) | 0.0046 (8) | −0.0051 (7) | −0.0011 (8) |
C29 | 0.0251 (8) | 0.0236 (8) | 0.0296 (10) | 0.0051 (7) | 0.0002 (7) | −0.0014 (7) |
Geometric parameters (Å, º) top
O1—C7 | 1.423 (2) | C10—H10B | 0.97 |
O1—C6 | 1.432 (2) | C11—C26 | 1.541 (2) |
O2—C7 | 1.418 (2) | C11—C12 | 1.565 (2) |
O2—C8 | 1.4439 (19) | C12—C13 | 1.538 (2) |
O3—C18 | 1.340 (2) | C12—H12A | 0.98 |
O3—C17 | 1.462 (2) | C13—C14 | 1.495 (2) |
O4—C18 | 1.222 (2) | C13—H13A | 0.97 |
O5—C16 | 1.427 (2) | C13—H13B | 0.97 |
O5—H5A | 0.92 (4) | C14—C15 | 1.333 (2) |
O6—C20 | 1.374 (2) | C14—H14A | 0.93 |
O6—C28 | 1.432 (2) | C15—C18 | 1.475 (2) |
O7—C24 | 1.372 (2) | C15—C16 | 1.510 (2) |
O7—C29 | 1.429 (2) | C16—C17 | 1.530 (2) |
C1—C27 | 1.328 (3) | C16—H16A | 0.98 |
C1—C2 | 1.508 (2) | C17—H17A | 0.97 |
C1—C12 | 1.515 (2) | C17—H17B | 0.97 |
C2—C3 | 1.533 (2) | C19—C20 | 1.397 (2) |
C2—H2A | 0.97 | C19—C24 | 1.406 (2) |
C2—H2B | 0.97 | C20—C21 | 1.398 (2) |
C3—C4 | 1.534 (2) | C21—C22 | 1.387 (3) |
C3—H3A | 0.97 | C21—H21A | 0.93 |
C3—H3B | 0.97 | C22—C23 | 1.389 (3) |
C4—C5 | 1.559 (2) | C22—H22A | 0.93 |
C4—C11 | 1.562 (2) | C23—C24 | 1.393 (2) |
C4—H4A | 0.98 | C23—H23A | 0.93 |
C5—C25 | 1.534 (2) | C25—H25A | 0.96 |
C5—C8 | 1.541 (2) | C25—H25B | 0.96 |
C5—C6 | 1.541 (2) | C25—H25C | 0.96 |
C6—H6A | 0.97 | C26—H26A | 0.96 |
C6—H6B | 0.97 | C26—H26B | 0.96 |
C7—C19 | 1.508 (2) | C26—H26C | 0.96 |
C7—H7A | 0.98 | C27—H27A | 1.03 |
C8—C9 | 1.523 (2) | C27—H27B | 0.97 |
C8—H8A | 0.98 | C28—H28A | 0.96 |
C9—C10 | 1.528 (2) | C28—H28B | 0.96 |
C9—H9A | 0.97 | C28—H28C | 0.96 |
C9—H9B | 0.97 | C29—H29A | 0.96 |
C10—C11 | 1.539 (2) | C29—H29B | 0.96 |
C10—H10A | 0.97 | C29—H29C | 0.96 |
| | | |
C7—O1—C6 | 110.28 (12) | C11—C12—H12A | 106.1 |
C7—O2—C8 | 113.43 (12) | C14—C13—C12 | 111.70 (14) |
C18—O3—C17 | 110.13 (13) | C14—C13—H13A | 109.3 |
C16—O5—H5A | 109 (2) | C12—C13—H13A | 109.3 |
C20—O6—C28 | 113.88 (14) | C14—C13—H13B | 109.3 |
C24—O7—C29 | 116.84 (14) | C12—C13—H13B | 109.3 |
C27—C1—C2 | 122.16 (17) | H13A—C13—H13B | 107.9 |
C27—C1—C12 | 125.22 (16) | C15—C14—C13 | 127.23 (15) |
C2—C1—C12 | 112.44 (14) | C15—C14—H14A | 116.4 |
C1—C2—C3 | 109.62 (15) | C13—C14—H14A | 116.4 |
C1—C2—H2A | 109.7 | C14—C15—C18 | 120.52 (15) |
C3—C2—H2A | 109.7 | C14—C15—C16 | 131.86 (15) |
C1—C2—H2B | 109.7 | C18—C15—C16 | 107.61 (14) |
C3—C2—H2B | 109.7 | O5—C16—C15 | 111.03 (15) |
H2A—C2—H2B | 108.2 | O5—C16—C17 | 108.47 (14) |
C2—C3—C4 | 111.04 (14) | C15—C16—C17 | 101.34 (13) |
C2—C3—H3A | 109.4 | O5—C16—H16A | 111.8 |
C4—C3—H3A | 109.4 | C15—C16—H16A | 111.8 |
C2—C3—H3B | 109.4 | C17—C16—H16A | 111.8 |
C4—C3—H3B | 109.4 | O3—C17—C16 | 106.92 (13) |
H3A—C3—H3B | 108.0 | O3—C17—H17A | 110.3 |
C3—C4—C5 | 113.29 (13) | C16—C17—H17A | 110.3 |
C3—C4—C11 | 112.19 (13) | O3—C17—H17B | 110.3 |
C5—C4—C11 | 116.90 (13) | C16—C17—H17B | 110.3 |
C3—C4—H4A | 104.3 | H17A—C17—H17B | 108.6 |
C5—C4—H4A | 104.3 | O4—C18—O3 | 121.42 (15) |
C11—C4—H4A | 104.3 | O4—C18—C15 | 128.56 (15) |
C25—C5—C8 | 107.73 (14) | O3—C18—C15 | 110.02 (14) |
C25—C5—C6 | 107.92 (14) | C20—C19—C24 | 118.24 (15) |
C8—C5—C6 | 107.59 (14) | C20—C19—C7 | 121.54 (15) |
C25—C5—C4 | 109.18 (13) | C24—C19—C7 | 120.19 (15) |
C8—C5—C4 | 108.75 (13) | O6—C20—C19 | 118.94 (15) |
C6—C5—C4 | 115.41 (14) | O6—C20—C21 | 119.81 (16) |
O1—C6—C5 | 110.53 (14) | C19—C20—C21 | 121.19 (16) |
O1—C6—H6A | 109.5 | C22—C21—C20 | 119.00 (17) |
C5—C6—H6A | 109.5 | C22—C21—H21A | 120.5 |
O1—C6—H6B | 109.5 | C20—C21—H21A | 120.5 |
C5—C6—H6B | 109.5 | C21—C22—C23 | 121.36 (17) |
H6A—C6—H6B | 108.1 | C21—C22—H22A | 119.3 |
O2—C7—O1 | 111.75 (13) | C23—C22—H22A | 119.3 |
O2—C7—C19 | 107.66 (13) | C22—C23—C24 | 119.00 (17) |
O1—C7—C19 | 109.56 (14) | C22—C23—H23A | 120.5 |
O2—C7—H7A | 109.3 | C24—C23—H23A | 120.5 |
O1—C7—H7A | 109.3 | O7—C24—C23 | 123.06 (16) |
C19—C7—H7A | 109.3 | O7—C24—C19 | 115.77 (15) |
O2—C8—C9 | 111.89 (13) | C23—C24—C19 | 121.16 (16) |
O2—C8—C5 | 110.65 (13) | C5—C25—H25A | 109.5 |
C9—C8—C5 | 113.88 (13) | C5—C25—H25B | 109.5 |
O2—C8—H8A | 106.6 | H25A—C25—H25B | 109.5 |
C9—C8—H8A | 106.6 | C5—C25—H25C | 109.5 |
C5—C8—H8A | 106.6 | H25A—C25—H25C | 109.5 |
C8—C9—C10 | 111.05 (14) | H25B—C25—H25C | 109.5 |
C8—C9—H9A | 109.4 | C11—C26—H26A | 109.5 |
C10—C9—H9A | 109.4 | C11—C26—H26B | 109.5 |
C8—C9—H9B | 109.4 | H26A—C26—H26B | 109.5 |
C10—C9—H9B | 109.4 | C11—C26—H26C | 109.5 |
H9A—C9—H9B | 108.0 | H26A—C26—H26C | 109.5 |
C9—C10—C11 | 112.59 (13) | H26B—C26—H26C | 109.5 |
C9—C10—H10A | 109.1 | C1—C27—H27A | 116.9 |
C11—C10—H10A | 109.1 | C1—C27—H27B | 121.3 |
C9—C10—H10B | 109.1 | H27A—C27—H27B | 121.6 |
C11—C10—H10B | 109.1 | O6—C28—H28A | 109.5 |
H10A—C10—H10B | 107.8 | O6—C28—H28B | 109.5 |
C10—C11—C26 | 110.30 (13) | H28A—C28—H28B | 109.5 |
C10—C11—C4 | 106.85 (13) | O6—C28—H28C | 109.5 |
C26—C11—C4 | 114.23 (13) | H28A—C28—H28C | 109.5 |
C10—C11—C12 | 109.55 (13) | H28B—C28—H28C | 109.5 |
C26—C11—C12 | 107.91 (13) | O7—C29—H29A | 109.5 |
C4—C11—C12 | 107.93 (12) | O7—C29—H29B | 109.5 |
C1—C12—C13 | 113.23 (14) | H29A—C29—H29B | 109.5 |
C1—C12—C11 | 110.00 (13) | O7—C29—H29C | 109.5 |
C13—C12—C11 | 114.65 (13) | H29A—C29—H29C | 109.5 |
C1—C12—H12A | 106.1 | H29B—C29—H29C | 109.5 |
C13—C12—H12A | 106.1 | | |
| | | |
C27—C1—C2—C3 | 116.39 (19) | C4—C11—C12—C1 | −56.71 (16) |
C12—C1—C2—C3 | −58.99 (19) | C10—C11—C12—C13 | 58.35 (18) |
C1—C2—C3—C4 | 55.7 (2) | C26—C11—C12—C13 | −61.76 (18) |
C2—C3—C4—C5 | 168.86 (14) | C4—C11—C12—C13 | 174.33 (13) |
C2—C3—C4—C11 | −56.10 (19) | C1—C12—C13—C14 | 62.05 (18) |
C3—C4—C5—C25 | −59.68 (18) | C11—C12—C13—C14 | −170.61 (13) |
C11—C4—C5—C25 | 167.51 (14) | C12—C13—C14—C15 | −151.81 (17) |
C3—C4—C5—C8 | −176.98 (14) | C13—C14—C15—C18 | −176.13 (16) |
C11—C4—C5—C8 | 50.21 (18) | C13—C14—C15—C16 | 3.6 (3) |
C3—C4—C5—C6 | 62.05 (19) | C14—C15—C16—O5 | 81.8 (2) |
C11—C4—C5—C6 | −70.75 (18) | C18—C15—C16—O5 | −98.40 (16) |
C7—O1—C6—C5 | −60.78 (18) | C14—C15—C16—C17 | −163.13 (19) |
C25—C5—C6—O1 | −60.61 (17) | C18—C15—C16—C17 | 16.64 (18) |
C8—C5—C6—O1 | 55.38 (18) | C18—O3—C17—C16 | 16.51 (18) |
C4—C5—C6—O1 | 176.97 (12) | O5—C16—C17—O3 | 97.21 (16) |
C8—O2—C7—O1 | −58.31 (18) | C15—C16—C17—O3 | −19.72 (17) |
C8—O2—C7—C19 | −178.66 (13) | C17—O3—C18—O4 | 174.77 (16) |
C6—O1—C7—O2 | 61.22 (17) | C17—O3—C18—C15 | −5.52 (18) |
C6—O1—C7—C19 | −179.55 (13) | C14—C15—C18—O4 | −8.3 (3) |
C7—O2—C8—C9 | −74.39 (17) | C16—C15—C18—O4 | 171.88 (18) |
C7—O2—C8—C5 | 53.75 (18) | C14—C15—C18—O3 | 171.99 (16) |
C25—C5—C8—O2 | 65.15 (17) | C16—C15—C18—O3 | −7.81 (19) |
C6—C5—C8—O2 | −50.98 (17) | O2—C7—C19—C20 | 68.1 (2) |
C4—C5—C8—O2 | −176.63 (12) | O1—C7—C19—C20 | −53.6 (2) |
C25—C5—C8—C9 | −167.80 (14) | O2—C7—C19—C24 | −109.91 (17) |
C6—C5—C8—C9 | 76.07 (17) | O1—C7—C19—C24 | 128.37 (16) |
C4—C5—C8—C9 | −49.58 (18) | C28—O6—C20—C19 | −114.51 (18) |
O2—C8—C9—C10 | −177.91 (13) | C28—O6—C20—C21 | 68.3 (2) |
C5—C8—C9—C10 | 55.69 (18) | C24—C19—C20—O6 | −179.58 (15) |
C8—C9—C10—C11 | −59.46 (18) | C7—C19—C20—O6 | 2.3 (2) |
C9—C10—C11—C26 | −68.59 (18) | C24—C19—C20—C21 | −2.4 (2) |
C9—C10—C11—C4 | 56.11 (17) | C7—C19—C20—C21 | 179.46 (16) |
C9—C10—C11—C12 | 172.78 (13) | O6—C20—C21—C22 | 179.04 (16) |
C3—C4—C11—C10 | 173.39 (14) | C19—C20—C21—C22 | 1.9 (3) |
C5—C4—C11—C10 | −53.31 (17) | C20—C21—C22—C23 | −0.3 (3) |
C3—C4—C11—C26 | −64.34 (18) | C21—C22—C23—C24 | −0.8 (3) |
C5—C4—C11—C26 | 68.96 (18) | C29—O7—C24—C23 | −1.9 (2) |
C3—C4—C11—C12 | 55.66 (17) | C29—O7—C24—C19 | 177.44 (16) |
C5—C4—C11—C12 | −171.04 (13) | C22—C23—C24—O7 | 179.56 (16) |
C27—C1—C12—C13 | 15.0 (3) | C22—C23—C24—C19 | 0.2 (3) |
C2—C1—C12—C13 | −169.75 (14) | C20—C19—C24—O7 | −178.03 (15) |
C27—C1—C12—C11 | −114.7 (2) | C7—C19—C24—O7 | 0.1 (2) |
C2—C1—C12—C11 | 60.52 (18) | C20—C19—C24—C23 | 1.4 (3) |
C10—C11—C12—C1 | −172.69 (13) | C7—C19—C24—C23 | 179.48 (16) |
C26—C11—C12—C1 | 67.20 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···O7 | 0.98 | 2.29 | 2.761 (2) | 109 |
C25—H25A···O2 | 0.96 | 2.53 | 2.939 (2) | 106 |
O5—H5A···O4i | 0.92 (4) | 1.87 (4) | 2.787 (2) | 174 (3) |
C23—H23A···Cg1ii | 0.93 | 2.82 | 3.679 (2) | 154 |
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y−1/2, −z. |