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The title compound, (E)-3-{2-[3-(2,6-dimethoxy­phenyl)-6a,10b-dimethyl-8-methyl­ene-deca­hydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl]ethyl­idene}-4-hydr­oxy-4,5-dihydro­furan-2(3H)-one, C29H38O7, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048999/ci2224sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048999/ci2224IIsup2.hkl
Contains datablock II

CCDC reference: 629630

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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

Computing details top

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,10b-dimethyl-8-methylene-decahydro- 1H-naphtho[2,1-d][1,3]dioxin-7-yl]ethylidene}-4-hydroxy-4,5-dihydrofuran- 2(3H)-one top
Crystal data top
C29H38O7F(000) = 1072
Mr = 498.59Dx = 1.330 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9044 reflections
a = 6.5021 (1) Åθ = 1.4–33.5°
b = 12.9728 (2) ŵ = 0.09 mm1
c = 29.5163 (4) ÅT = 100 K
V = 2489.71 (6) Å3Block, colourless
Z = 40.37 × 0.26 × 0.21 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
5470 independent reflections
Radiation source: fine-focus sealed tube4724 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 8.33 pixels mm-1θmax = 33.5°, θmin = 1.4°
ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 2019
Tmin = 0.873, Tmax = 0.981l = 4345
44842 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H 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 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
xyzUiso*/Ueq
O10.2961 (2)0.00552 (10)0.13187 (4)0.0190 (2)
O20.05890 (18)0.11704 (10)0.10508 (4)0.0180 (2)
O30.75262 (19)0.23661 (10)0.44792 (4)0.0203 (2)
O40.91111 (19)0.13808 (11)0.39653 (5)0.0232 (3)
O50.2838 (2)0.17083 (12)0.44088 (5)0.0239 (3)
O60.2271 (2)0.04408 (10)0.04040 (4)0.0211 (3)
O70.5386 (2)0.25688 (10)0.10018 (4)0.0216 (3)
C10.3146 (3)0.03003 (14)0.30344 (6)0.0188 (3)
C20.3396 (3)0.11765 (14)0.27032 (6)0.0221 (3)
H2A0.32730.18290.28610.027*
H2B0.47490.11450.25660.027*
C30.1739 (3)0.11012 (13)0.23350 (6)0.0207 (3)
H3A0.03950.12030.24700.025*
H3B0.19540.16410.21130.025*
C40.1804 (3)0.00477 (12)0.20994 (5)0.0154 (3)
H4A0.32180.00100.19870.018*
C50.0455 (3)0.00013 (13)0.16631 (5)0.0156 (3)
C60.1867 (3)0.01703 (14)0.17365 (6)0.0179 (3)
H6A0.20960.08570.18570.021*
H6B0.23790.03240.19560.021*
C70.2687 (2)0.09577 (13)0.11437 (6)0.0171 (3)
H7A0.32060.14600.13640.021*
C80.0728 (2)0.10685 (13)0.14421 (5)0.0164 (3)
H8A0.21460.10990.13310.020*
C90.0468 (3)0.19657 (13)0.17701 (6)0.0186 (3)
H9A0.09400.19840.18780.022*
H9B0.07410.26080.16130.022*
C100.1930 (3)0.18636 (12)0.21728 (6)0.0176 (3)
H10A0.17400.24490.23730.021*
H10B0.33370.18790.20640.021*
C110.1584 (2)0.08632 (12)0.24422 (5)0.0145 (3)
C120.3308 (2)0.07453 (13)0.28083 (6)0.0159 (3)
H12A0.46150.07430.26430.019*
C130.3444 (3)0.16423 (14)0.31478 (6)0.0183 (3)
H13A0.34680.22900.29830.022*
H13B0.22320.16390.33390.022*
C140.5323 (3)0.15662 (13)0.34375 (6)0.0175 (3)
H14A0.64500.12330.33110.021*
C150.5564 (2)0.19234 (13)0.38577 (6)0.0160 (3)
C160.4091 (3)0.24461 (14)0.41797 (6)0.0177 (3)
H16A0.32620.29730.40270.021*
C170.5579 (3)0.29206 (14)0.45230 (6)0.0200 (3)
H17A0.57750.36480.44600.024*
H17B0.50400.28490.48280.024*
C180.7570 (3)0.18425 (13)0.40881 (6)0.0178 (3)
C190.3862 (3)0.10678 (14)0.07061 (6)0.0177 (3)
C200.3590 (3)0.03773 (13)0.03481 (6)0.0181 (3)
C210.4698 (3)0.04796 (15)0.00551 (6)0.0212 (3)
H21A0.45350.00040.02880.025*
C220.6045 (3)0.13018 (15)0.01028 (6)0.0228 (3)
H22A0.67810.13750.03710.027*
C230.6316 (3)0.20181 (15)0.02417 (6)0.0216 (3)
H23A0.72110.25700.02040.026*
C240.5226 (3)0.18967 (14)0.06447 (6)0.0185 (3)
C250.1214 (3)0.08112 (15)0.13246 (6)0.0228 (3)
H25A0.05980.06880.10340.034*
H25B0.08370.14850.14300.034*
H25C0.26840.07680.12980.034*
C260.0504 (3)0.09003 (14)0.26891 (6)0.0193 (3)
H26A0.03790.13130.29580.029*
H26B0.09120.02140.27710.029*
H26C0.15210.11970.24930.029*
C270.2686 (3)0.04575 (15)0.34674 (6)0.0255 (4)
H27A0.26300.12100.35760.031*
H27B0.25400.01140.36770.031*
C280.0497 (3)0.04028 (16)0.01169 (7)0.0268 (4)
H28A0.03260.10070.01650.040*
H28B0.02970.02000.01870.040*
H28C0.09260.03760.01940.040*
C290.6697 (3)0.34415 (15)0.09405 (7)0.0261 (4)
H29A0.66900.38540.12110.039*
H29B0.80730.32120.08800.039*
H29C0.62090.38460.06900.039*
H5A0.166 (6)0.160 (3)0.4243 (10)0.064 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0177 (5)0.0214 (6)0.0180 (6)0.0041 (5)0.0030 (4)0.0028 (5)
O20.0148 (5)0.0232 (6)0.0160 (5)0.0036 (4)0.0013 (4)0.0023 (5)
O30.0146 (5)0.0284 (6)0.0179 (5)0.0001 (5)0.0015 (5)0.0040 (5)
O40.0139 (5)0.0298 (7)0.0258 (7)0.0017 (5)0.0013 (5)0.0047 (5)
O50.0142 (5)0.0381 (7)0.0194 (6)0.0055 (5)0.0006 (5)0.0043 (5)
O60.0200 (6)0.0230 (6)0.0204 (6)0.0012 (5)0.0027 (5)0.0014 (5)
O70.0228 (6)0.0206 (6)0.0215 (6)0.0036 (5)0.0029 (5)0.0013 (5)
C10.0157 (7)0.0203 (8)0.0205 (8)0.0003 (6)0.0036 (6)0.0011 (6)
C20.0243 (8)0.0174 (7)0.0248 (9)0.0014 (6)0.0048 (7)0.0013 (6)
C30.0239 (8)0.0158 (7)0.0225 (8)0.0014 (6)0.0036 (6)0.0013 (6)
C40.0144 (6)0.0153 (7)0.0166 (7)0.0008 (5)0.0010 (5)0.0005 (5)
C50.0148 (6)0.0163 (7)0.0157 (7)0.0004 (6)0.0000 (5)0.0018 (5)
C60.0170 (7)0.0203 (7)0.0164 (7)0.0037 (6)0.0017 (6)0.0028 (6)
C70.0144 (6)0.0189 (7)0.0180 (7)0.0009 (6)0.0003 (6)0.0007 (6)
C80.0139 (6)0.0208 (7)0.0144 (7)0.0018 (5)0.0005 (5)0.0003 (6)
C90.0205 (7)0.0168 (7)0.0184 (7)0.0005 (6)0.0034 (6)0.0008 (6)
C100.0173 (7)0.0172 (7)0.0181 (7)0.0013 (6)0.0018 (6)0.0001 (6)
C110.0123 (6)0.0157 (7)0.0156 (7)0.0004 (5)0.0002 (5)0.0008 (5)
C120.0129 (6)0.0180 (7)0.0167 (7)0.0002 (5)0.0009 (5)0.0021 (6)
C130.0154 (7)0.0216 (7)0.0179 (7)0.0002 (6)0.0020 (6)0.0027 (6)
C140.0132 (6)0.0210 (7)0.0184 (7)0.0012 (6)0.0002 (6)0.0013 (6)
C150.0117 (6)0.0188 (7)0.0175 (7)0.0012 (5)0.0004 (5)0.0001 (6)
C160.0152 (7)0.0231 (8)0.0149 (7)0.0010 (6)0.0002 (5)0.0006 (6)
C170.0159 (7)0.0260 (8)0.0180 (8)0.0003 (6)0.0008 (6)0.0047 (6)
C180.0146 (7)0.0218 (8)0.0171 (7)0.0018 (6)0.0005 (6)0.0003 (6)
C190.0149 (6)0.0225 (8)0.0158 (7)0.0019 (6)0.0001 (5)0.0008 (6)
C200.0150 (7)0.0198 (7)0.0197 (8)0.0025 (6)0.0011 (6)0.0015 (6)
C210.0204 (8)0.0263 (8)0.0169 (7)0.0040 (7)0.0005 (6)0.0018 (6)
C220.0172 (7)0.0322 (9)0.0190 (8)0.0025 (7)0.0031 (6)0.0030 (7)
C230.0171 (7)0.0265 (8)0.0213 (8)0.0001 (6)0.0020 (6)0.0027 (7)
C240.0157 (7)0.0217 (8)0.0182 (7)0.0018 (6)0.0003 (6)0.0003 (6)
C250.0235 (8)0.0246 (8)0.0203 (8)0.0033 (7)0.0017 (7)0.0067 (7)
C260.0137 (6)0.0265 (8)0.0177 (7)0.0002 (6)0.0006 (6)0.0027 (6)
C270.0282 (9)0.0255 (9)0.0227 (9)0.0035 (7)0.0040 (7)0.0036 (7)
C280.0236 (8)0.0321 (10)0.0248 (9)0.0046 (8)0.0051 (7)0.0011 (8)
C290.0251 (8)0.0236 (8)0.0296 (10)0.0051 (7)0.0002 (7)0.0014 (7)
Geometric parameters (Å, º) top
O1—C71.423 (2)C10—H10B0.97
O1—C61.432 (2)C11—C261.541 (2)
O2—C71.418 (2)C11—C121.565 (2)
O2—C81.4439 (19)C12—C131.538 (2)
O3—C181.340 (2)C12—H12A0.98
O3—C171.462 (2)C13—C141.495 (2)
O4—C181.222 (2)C13—H13A0.97
O5—C161.427 (2)C13—H13B0.97
O5—H5A0.92 (4)C14—C151.333 (2)
O6—C201.374 (2)C14—H14A0.93
O6—C281.432 (2)C15—C181.475 (2)
O7—C241.372 (2)C15—C161.510 (2)
O7—C291.429 (2)C16—C171.530 (2)
C1—C271.328 (3)C16—H16A0.98
C1—C21.508 (2)C17—H17A0.97
C1—C121.515 (2)C17—H17B0.97
C2—C31.533 (2)C19—C201.397 (2)
C2—H2A0.97C19—C241.406 (2)
C2—H2B0.97C20—C211.398 (2)
C3—C41.534 (2)C21—C221.387 (3)
C3—H3A0.97C21—H21A0.93
C3—H3B0.97C22—C231.389 (3)
C4—C51.559 (2)C22—H22A0.93
C4—C111.562 (2)C23—C241.393 (2)
C4—H4A0.98C23—H23A0.93
C5—C251.534 (2)C25—H25A0.96
C5—C81.541 (2)C25—H25B0.96
C5—C61.541 (2)C25—H25C0.96
C6—H6A0.97C26—H26A0.96
C6—H6B0.97C26—H26B0.96
C7—C191.508 (2)C26—H26C0.96
C7—H7A0.98C27—H27A1.03
C8—C91.523 (2)C27—H27B0.97
C8—H8A0.98C28—H28A0.96
C9—C101.528 (2)C28—H28B0.96
C9—H9A0.97C28—H28C0.96
C9—H9B0.97C29—H29A0.96
C10—C111.539 (2)C29—H29B0.96
C10—H10A0.97C29—H29C0.96
C7—O1—C6110.28 (12)C11—C12—H12A106.1
C7—O2—C8113.43 (12)C14—C13—C12111.70 (14)
C18—O3—C17110.13 (13)C14—C13—H13A109.3
C16—O5—H5A109 (2)C12—C13—H13A109.3
C20—O6—C28113.88 (14)C14—C13—H13B109.3
C24—O7—C29116.84 (14)C12—C13—H13B109.3
C27—C1—C2122.16 (17)H13A—C13—H13B107.9
C27—C1—C12125.22 (16)C15—C14—C13127.23 (15)
C2—C1—C12112.44 (14)C15—C14—H14A116.4
C1—C2—C3109.62 (15)C13—C14—H14A116.4
C1—C2—H2A109.7C14—C15—C18120.52 (15)
C3—C2—H2A109.7C14—C15—C16131.86 (15)
C1—C2—H2B109.7C18—C15—C16107.61 (14)
C3—C2—H2B109.7O5—C16—C15111.03 (15)
H2A—C2—H2B108.2O5—C16—C17108.47 (14)
C2—C3—C4111.04 (14)C15—C16—C17101.34 (13)
C2—C3—H3A109.4O5—C16—H16A111.8
C4—C3—H3A109.4C15—C16—H16A111.8
C2—C3—H3B109.4C17—C16—H16A111.8
C4—C3—H3B109.4O3—C17—C16106.92 (13)
H3A—C3—H3B108.0O3—C17—H17A110.3
C3—C4—C5113.29 (13)C16—C17—H17A110.3
C3—C4—C11112.19 (13)O3—C17—H17B110.3
C5—C4—C11116.90 (13)C16—C17—H17B110.3
C3—C4—H4A104.3H17A—C17—H17B108.6
C5—C4—H4A104.3O4—C18—O3121.42 (15)
C11—C4—H4A104.3O4—C18—C15128.56 (15)
C25—C5—C8107.73 (14)O3—C18—C15110.02 (14)
C25—C5—C6107.92 (14)C20—C19—C24118.24 (15)
C8—C5—C6107.59 (14)C20—C19—C7121.54 (15)
C25—C5—C4109.18 (13)C24—C19—C7120.19 (15)
C8—C5—C4108.75 (13)O6—C20—C19118.94 (15)
C6—C5—C4115.41 (14)O6—C20—C21119.81 (16)
O1—C6—C5110.53 (14)C19—C20—C21121.19 (16)
O1—C6—H6A109.5C22—C21—C20119.00 (17)
C5—C6—H6A109.5C22—C21—H21A120.5
O1—C6—H6B109.5C20—C21—H21A120.5
C5—C6—H6B109.5C21—C22—C23121.36 (17)
H6A—C6—H6B108.1C21—C22—H22A119.3
O2—C7—O1111.75 (13)C23—C22—H22A119.3
O2—C7—C19107.66 (13)C22—C23—C24119.00 (17)
O1—C7—C19109.56 (14)C22—C23—H23A120.5
O2—C7—H7A109.3C24—C23—H23A120.5
O1—C7—H7A109.3O7—C24—C23123.06 (16)
C19—C7—H7A109.3O7—C24—C19115.77 (15)
O2—C8—C9111.89 (13)C23—C24—C19121.16 (16)
O2—C8—C5110.65 (13)C5—C25—H25A109.5
C9—C8—C5113.88 (13)C5—C25—H25B109.5
O2—C8—H8A106.6H25A—C25—H25B109.5
C9—C8—H8A106.6C5—C25—H25C109.5
C5—C8—H8A106.6H25A—C25—H25C109.5
C8—C9—C10111.05 (14)H25B—C25—H25C109.5
C8—C9—H9A109.4C11—C26—H26A109.5
C10—C9—H9A109.4C11—C26—H26B109.5
C8—C9—H9B109.4H26A—C26—H26B109.5
C10—C9—H9B109.4C11—C26—H26C109.5
H9A—C9—H9B108.0H26A—C26—H26C109.5
C9—C10—C11112.59 (13)H26B—C26—H26C109.5
C9—C10—H10A109.1C1—C27—H27A116.9
C11—C10—H10A109.1C1—C27—H27B121.3
C9—C10—H10B109.1H27A—C27—H27B121.6
C11—C10—H10B109.1O6—C28—H28A109.5
H10A—C10—H10B107.8O6—C28—H28B109.5
C10—C11—C26110.30 (13)H28A—C28—H28B109.5
C10—C11—C4106.85 (13)O6—C28—H28C109.5
C26—C11—C4114.23 (13)H28A—C28—H28C109.5
C10—C11—C12109.55 (13)H28B—C28—H28C109.5
C26—C11—C12107.91 (13)O7—C29—H29A109.5
C4—C11—C12107.93 (12)O7—C29—H29B109.5
C1—C12—C13113.23 (14)H29A—C29—H29B109.5
C1—C12—C11110.00 (13)O7—C29—H29C109.5
C13—C12—C11114.65 (13)H29A—C29—H29C109.5
C1—C12—H12A106.1H29B—C29—H29C109.5
C13—C12—H12A106.1
C27—C1—C2—C3116.39 (19)C4—C11—C12—C156.71 (16)
C12—C1—C2—C358.99 (19)C10—C11—C12—C1358.35 (18)
C1—C2—C3—C455.7 (2)C26—C11—C12—C1361.76 (18)
C2—C3—C4—C5168.86 (14)C4—C11—C12—C13174.33 (13)
C2—C3—C4—C1156.10 (19)C1—C12—C13—C1462.05 (18)
C3—C4—C5—C2559.68 (18)C11—C12—C13—C14170.61 (13)
C11—C4—C5—C25167.51 (14)C12—C13—C14—C15151.81 (17)
C3—C4—C5—C8176.98 (14)C13—C14—C15—C18176.13 (16)
C11—C4—C5—C850.21 (18)C13—C14—C15—C163.6 (3)
C3—C4—C5—C662.05 (19)C14—C15—C16—O581.8 (2)
C11—C4—C5—C670.75 (18)C18—C15—C16—O598.40 (16)
C7—O1—C6—C560.78 (18)C14—C15—C16—C17163.13 (19)
C25—C5—C6—O160.61 (17)C18—C15—C16—C1716.64 (18)
C8—C5—C6—O155.38 (18)C18—O3—C17—C1616.51 (18)
C4—C5—C6—O1176.97 (12)O5—C16—C17—O397.21 (16)
C8—O2—C7—O158.31 (18)C15—C16—C17—O319.72 (17)
C8—O2—C7—C19178.66 (13)C17—O3—C18—O4174.77 (16)
C6—O1—C7—O261.22 (17)C17—O3—C18—C155.52 (18)
C6—O1—C7—C19179.55 (13)C14—C15—C18—O48.3 (3)
C7—O2—C8—C974.39 (17)C16—C15—C18—O4171.88 (18)
C7—O2—C8—C553.75 (18)C14—C15—C18—O3171.99 (16)
C25—C5—C8—O265.15 (17)C16—C15—C18—O37.81 (19)
C6—C5—C8—O250.98 (17)O2—C7—C19—C2068.1 (2)
C4—C5—C8—O2176.63 (12)O1—C7—C19—C2053.6 (2)
C25—C5—C8—C9167.80 (14)O2—C7—C19—C24109.91 (17)
C6—C5—C8—C976.07 (17)O1—C7—C19—C24128.37 (16)
C4—C5—C8—C949.58 (18)C28—O6—C20—C19114.51 (18)
O2—C8—C9—C10177.91 (13)C28—O6—C20—C2168.3 (2)
C5—C8—C9—C1055.69 (18)C24—C19—C20—O6179.58 (15)
C8—C9—C10—C1159.46 (18)C7—C19—C20—O62.3 (2)
C9—C10—C11—C2668.59 (18)C24—C19—C20—C212.4 (2)
C9—C10—C11—C456.11 (17)C7—C19—C20—C21179.46 (16)
C9—C10—C11—C12172.78 (13)O6—C20—C21—C22179.04 (16)
C3—C4—C11—C10173.39 (14)C19—C20—C21—C221.9 (3)
C5—C4—C11—C1053.31 (17)C20—C21—C22—C230.3 (3)
C3—C4—C11—C2664.34 (18)C21—C22—C23—C240.8 (3)
C5—C4—C11—C2668.96 (18)C29—O7—C24—C231.9 (2)
C3—C4—C11—C1255.66 (17)C29—O7—C24—C19177.44 (16)
C5—C4—C11—C12171.04 (13)C22—C23—C24—O7179.56 (16)
C27—C1—C12—C1315.0 (3)C22—C23—C24—C190.2 (3)
C2—C1—C12—C13169.75 (14)C20—C19—C24—O7178.03 (15)
C27—C1—C12—C11114.7 (2)C7—C19—C24—O70.1 (2)
C2—C1—C12—C1160.52 (18)C20—C19—C24—C231.4 (3)
C10—C11—C12—C1172.69 (13)C7—C19—C24—C23179.48 (16)
C26—C11—C12—C167.20 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···O70.982.292.761 (2)109
C25—H25A···O20.962.532.939 (2)106
O5—H5A···O4i0.92 (4)1.87 (4)2.787 (2)174 (3)
C23—H23A···Cg1ii0.932.823.679 (2)154
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y1/2, z.
 

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