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The title compound, (E)-3-{2-[3-(2-bromo­phen­yl)-6a,10b-di­methyl-8-methyl­eneperhydro­naphtho[2,1-d][1,3]dioxin-7-yl]ethyl­idene}-4-hydr­oxy-4,5-dihydro­furan-2(3H)-one, C27H33BrO5, an andrographolide derivative, was semi-synthesized using andrographolide as a starting material. The structure contains three fused six-membered rings adopting chair conformations and a five-membered ring adopting an envelope conformation. The 2-bromo­phenyl group is twisted away from the attached ring. O—H...O hydrogen bonds in the structure form chains along the b axis which are inter­linked via C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806000705/ci6748sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806000705/ci6748IIsup2.hkl
Contains datablock II

CCDC reference: 298398

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.109
  • Data-to-parameter ratio = 36.3

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.417 0.732 Tmin(prime) and Tmax expected: 0.489 0.716 RR(prime) = 0.835 Please check that your absorption correction is appropriate. PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
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 36.23 From the CIF: _reflns_number_total 10919 Count of symmetry unique reflns 6396 Completeness (_total/calc) 170.72% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 4523 Fraction of Friedel pairs measured 0.707 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
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 S. R. Jada 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-bromophenyl)-6a,10b-dimethyl-8- methyleneperhydronaphtho[2,1-d][1,3]dioxin-7-yl]ethylidene}-4-hydroxy- 4,5-dihydrofuran-2(3H)-one top
Crystal data top
C27H33BrO5F(000) = 1080
Mr = 517.44Dx = 1.437 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5896 reflections
a = 7.6735 (1) Åθ = 1.5–36.2°
b = 11.7744 (2) ŵ = 1.76 mm1
c = 26.4742 (5) ÅT = 297 K
V = 2391.97 (7) Å3Block, colourless
Z = 40.40 × 0.26 × 0.19 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
10919 independent reflections
Radiation source: fine-focus sealed tube4609 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
Detector resolution: 8.33 pixels mm-1θmax = 36.2°, θmin = 1.5°
ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1519
Tmin = 0.417, Tmax = 0.732l = 4324
36359 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.0329P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.001
10919 reflectionsΔρmax = 0.30 e Å3
301 parametersΔρmin = 0.24 e Å3
0 restraintsAbsolute structure: Flack (1983), 4719 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.011 (6)
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
xyzUiso*/Ueq
Br10.16374 (4)0.65047 (2)0.393923 (11)0.05707 (10)
O10.2204 (2)0.53554 (12)0.42700 (6)0.0430 (4)
O20.3664 (2)0.68401 (12)0.46748 (6)0.0428 (4)
O30.1087 (3)0.07353 (15)0.73084 (8)0.0655 (6)
O40.1794 (3)0.08101 (15)0.73310 (7)0.0668 (6)
O50.1790 (3)0.17515 (15)0.74915 (7)0.0601 (5)
H5A0.14180.24000.74570.090*
C10.0366 (3)0.7293 (2)0.36961 (9)0.0381 (5)
C20.0163 (4)0.7943 (2)0.32641 (9)0.0474 (7)
H20.09120.79940.31040.057*
C30.1598 (4)0.8512 (2)0.30780 (9)0.0510 (6)
H30.14880.89500.27870.061*
C40.3181 (4)0.8442 (2)0.33148 (9)0.0514 (6)
H40.41390.88270.31850.062*
C50.3349 (4)0.77991 (19)0.37466 (9)0.0436 (6)
H50.44270.77540.39060.052*
C60.1933 (3)0.72134 (17)0.39493 (9)0.0363 (5)
C70.2135 (3)0.65126 (19)0.44227 (8)0.0368 (5)
H70.11260.66320.46440.044*
C80.2423 (3)0.45869 (19)0.46912 (9)0.0397 (6)
H80.26860.38420.45450.048*
C90.0763 (3)0.4441 (2)0.49913 (10)0.0487 (7)
H9A0.01630.41820.47700.058*
H9B0.04170.51650.51340.058*
C100.1038 (3)0.3574 (2)0.54169 (9)0.0481 (6)
H10A0.13270.28450.52690.058*
H10B0.00460.34860.56010.058*
C110.2486 (3)0.39119 (18)0.57905 (8)0.0328 (5)
C120.2893 (3)0.28850 (18)0.61521 (8)0.0356 (5)
H120.32440.22510.59350.043*
C130.4461 (3)0.31655 (18)0.64788 (9)0.0378 (5)
C140.6075 (3)0.3479 (2)0.61915 (9)0.0476 (6)
H14A0.65050.28180.60120.057*
H14B0.69710.37210.64270.057*
C150.5713 (3)0.4433 (2)0.58142 (9)0.0442 (6)
H15A0.54610.51300.59960.053*
H15B0.67390.45610.56080.053*
C160.4171 (3)0.41317 (19)0.54751 (8)0.0329 (5)
H160.44710.33860.53350.040*
C170.4017 (3)0.49201 (18)0.50032 (8)0.0339 (5)
C180.3862 (3)0.61880 (18)0.51291 (9)0.0407 (6)
H18A0.28640.63110.53470.049*
H18B0.48980.64360.53080.049*
C190.1325 (3)0.2473 (2)0.64542 (10)0.0445 (6)
H19A0.10460.30410.67070.053*
H19B0.03340.24160.62280.053*
C200.1555 (4)0.13475 (19)0.67157 (8)0.0418 (5)
H200.26520.10120.67070.050*
C210.0300 (3)0.08074 (19)0.69569 (9)0.0389 (6)
C220.0483 (4)0.0313 (2)0.72088 (9)0.0466 (6)
C230.2430 (4)0.0001 (3)0.71016 (13)0.0636 (8)
H23A0.34100.00540.73320.076*
H23B0.28440.02920.67800.076*
C240.1576 (4)0.1144 (2)0.70334 (10)0.0465 (6)
H240.20470.15580.67430.056*
C250.5639 (4)0.4780 (2)0.46701 (10)0.0566 (7)
H25A0.54650.51710.43560.085*
H25B0.58330.39880.46050.085*
H25C0.66330.50930.48410.085*
C260.1885 (3)0.49167 (19)0.61121 (10)0.0477 (6)
H26A0.15690.55380.58960.072*
H26B0.28140.51480.63320.072*
H26C0.08940.46950.63100.072*
C270.4432 (4)0.3187 (2)0.69820 (10)0.0538 (7)
H27A0.54230.34000.71610.065*
H27B0.34200.29910.71540.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04786 (14)0.06360 (18)0.05976 (17)0.01636 (14)0.00361 (15)0.00277 (15)
O10.0651 (12)0.0290 (8)0.0350 (9)0.0052 (8)0.0084 (8)0.0026 (7)
O20.0587 (11)0.0292 (8)0.0405 (9)0.0094 (8)0.0145 (8)0.0081 (7)
O30.0839 (16)0.0363 (11)0.0764 (14)0.0098 (11)0.0205 (12)0.0063 (10)
O40.0875 (15)0.0456 (11)0.0673 (13)0.0166 (12)0.0032 (12)0.0133 (9)
O50.0670 (12)0.0449 (10)0.0684 (12)0.0004 (11)0.0231 (11)0.0058 (9)
C10.0449 (14)0.0356 (12)0.0338 (12)0.0026 (11)0.0006 (11)0.0004 (10)
C20.0554 (16)0.0503 (15)0.0367 (13)0.0077 (13)0.0121 (12)0.0013 (12)
C30.0752 (18)0.0469 (13)0.0310 (11)0.0034 (17)0.0008 (13)0.0068 (12)
C40.0578 (16)0.0529 (15)0.0433 (13)0.0078 (16)0.0063 (13)0.0075 (13)
C50.0411 (13)0.0450 (13)0.0446 (13)0.0033 (13)0.0009 (12)0.0069 (11)
C60.0458 (13)0.0285 (11)0.0344 (11)0.0004 (9)0.0002 (12)0.0008 (10)
C70.0460 (13)0.0291 (11)0.0352 (11)0.0009 (11)0.0036 (10)0.0006 (10)
C80.0582 (15)0.0236 (11)0.0372 (13)0.0038 (11)0.0067 (12)0.0029 (10)
C90.0426 (14)0.0499 (15)0.0537 (16)0.0127 (13)0.0135 (13)0.0138 (13)
C100.0446 (13)0.0459 (14)0.0538 (15)0.0116 (12)0.0064 (11)0.0161 (13)
C110.0360 (12)0.0291 (11)0.0333 (12)0.0020 (10)0.0023 (10)0.0024 (9)
C120.0397 (12)0.0300 (11)0.0370 (13)0.0033 (9)0.0068 (10)0.0039 (9)
C130.0433 (13)0.0314 (12)0.0387 (13)0.0068 (11)0.0010 (11)0.0064 (10)
C140.0377 (12)0.0575 (15)0.0477 (14)0.0070 (13)0.0024 (10)0.0114 (13)
C150.0369 (13)0.0484 (14)0.0474 (14)0.0015 (12)0.0008 (11)0.0133 (12)
C160.0353 (11)0.0299 (11)0.0335 (12)0.0033 (10)0.0038 (10)0.0029 (9)
C170.0380 (12)0.0316 (12)0.0322 (12)0.0001 (10)0.0029 (10)0.0054 (10)
C180.0516 (14)0.0324 (12)0.0380 (12)0.0067 (11)0.0138 (11)0.0033 (10)
C190.0450 (15)0.0427 (13)0.0458 (14)0.0036 (12)0.0087 (12)0.0147 (11)
C200.0453 (13)0.0399 (13)0.0403 (12)0.0091 (13)0.0051 (12)0.0069 (10)
C210.0509 (15)0.0337 (13)0.0322 (12)0.0003 (12)0.0027 (11)0.0015 (10)
C220.0696 (19)0.0321 (13)0.0381 (13)0.0019 (14)0.0074 (14)0.0000 (11)
C230.0619 (19)0.0562 (18)0.073 (2)0.0153 (16)0.0031 (17)0.0009 (16)
C240.0505 (15)0.0429 (13)0.0462 (14)0.0030 (13)0.0034 (13)0.0075 (11)
C250.0555 (17)0.0600 (17)0.0542 (17)0.0079 (14)0.0157 (14)0.0164 (14)
C260.0566 (15)0.0386 (12)0.0480 (14)0.0129 (12)0.0133 (14)0.0034 (11)
C270.0639 (17)0.0542 (17)0.0432 (15)0.0007 (15)0.0018 (14)0.0031 (12)
Geometric parameters (Å, º) top
Br1—C11.908 (2)C12—C191.524 (3)
O1—C71.422 (3)C12—H120.98
O1—C81.446 (3)C13—C271.332 (3)
O2—C71.404 (3)C13—C141.500 (3)
O2—C181.435 (3)C14—C151.529 (3)
O3—C221.329 (3)C14—H14A0.97
O3—C231.452 (4)C14—H14B0.97
O4—C221.208 (3)C15—C161.527 (3)
O5—C241.418 (3)C15—H15A0.97
O5—H5A0.82C15—H15B0.97
C1—C61.380 (3)C16—C171.561 (3)
C1—C21.385 (3)C16—H160.98
C2—C31.380 (4)C17—C251.534 (3)
C2—H20.93C17—C181.534 (3)
C3—C41.370 (4)C18—H18A0.97
C3—H30.93C18—H18B0.97
C4—C51.377 (3)C19—C201.505 (3)
C4—H40.93C19—H19A0.97
C5—C61.394 (3)C19—H19B0.97
C5—H50.93C20—C211.319 (3)
C6—C71.509 (3)C20—H200.93
C7—H70.98C21—C221.485 (4)
C8—C91.512 (4)C21—C241.507 (4)
C8—C171.527 (3)C23—C241.510 (4)
C8—H80.98C23—H23A0.97
C9—C101.535 (3)C23—H23B0.97
C9—H9A0.97C24—H240.98
C9—H9B0.97C25—H25A0.96
C10—C111.540 (3)C25—H25B0.96
C10—H10A0.97C25—H25C0.96
C10—H10B0.97C26—H26A0.96
C11—C261.529 (3)C26—H26B0.96
C11—C161.561 (3)C26—H26C0.96
C11—C121.574 (3)C27—H27A0.93
C12—C131.518 (3)C27—H27B0.93
C7—O1—C8112.62 (16)C16—C15—C14110.7 (2)
C7—O2—C18109.88 (17)C16—C15—H15A109.5
C22—O3—C23110.2 (2)C14—C15—H15A109.5
C24—O5—H5A109.5C16—C15—H15B109.5
C6—C1—C2122.5 (2)C14—C15—H15B109.5
C6—C1—Br1120.34 (17)H15A—C15—H15B108.1
C2—C1—Br1117.19 (19)C15—C16—C17113.02 (19)
C3—C2—C1118.3 (2)C15—C16—C11111.47 (17)
C3—C2—H2120.9C17—C16—C11117.64 (18)
C1—C2—H2120.9C15—C16—H16104.4
C4—C3—C2121.0 (2)C17—C16—H16104.4
C4—C3—H3119.5C11—C16—H16104.4
C2—C3—H3119.5C8—C17—C25108.12 (19)
C3—C4—C5119.7 (3)C8—C17—C18107.79 (19)
C3—C4—H4120.1C25—C17—C18107.0 (2)
C5—C4—H4120.1C8—C17—C16109.93 (18)
C4—C5—C6121.2 (3)C25—C17—C16109.54 (19)
C4—C5—H5119.4C18—C17—C16114.25 (18)
C6—C5—H5119.4O2—C18—C17110.29 (19)
C1—C6—C5117.3 (2)O2—C18—H18A109.6
C1—C6—C7122.0 (2)C17—C18—H18A109.6
C5—C6—C7120.7 (2)O2—C18—H18B109.6
O2—C7—O1111.52 (19)C17—C18—H18B109.6
O2—C7—C6109.29 (18)H18A—C18—H18B108.1
O1—C7—C6106.96 (17)C20—C19—C12115.4 (2)
O2—C7—H7109.7C20—C19—H19A108.4
O1—C7—H7109.7C12—C19—H19A108.4
C6—C7—H7109.7C20—C19—H19B108.4
O1—C8—C9112.2 (2)C12—C19—H19B108.4
O1—C8—C17110.46 (18)H19A—C19—H19B107.5
C9—C8—C17114.84 (19)C21—C20—C19124.2 (2)
O1—C8—H8106.2C21—C20—H20117.9
C9—C8—H8106.2C19—C20—H20117.9
C17—C8—H8106.2C20—C21—C22125.2 (2)
C8—C9—C10110.2 (2)C20—C21—C24129.5 (2)
C8—C9—H9A109.6C22—C21—C24105.3 (2)
C10—C9—H9A109.6O4—C22—O3121.4 (2)
C8—C9—H9B109.6O4—C22—C21129.0 (3)
C10—C9—H9B109.6O3—C22—C21109.6 (2)
H9A—C9—H9B108.1O3—C23—C24105.6 (2)
C9—C10—C11113.5 (2)O3—C23—H23A110.6
C9—C10—H10A108.9C24—C23—H23A110.6
C11—C10—H10A108.9O3—C23—H23B110.6
C9—C10—H10B108.9C24—C23—H23B110.6
C11—C10—H10B108.9H23A—C23—H23B108.8
H10A—C10—H10B107.7O5—C24—C21111.0 (2)
C26—C11—C10109.9 (2)O5—C24—C23107.3 (2)
C26—C11—C16114.80 (19)C21—C24—C23101.3 (2)
C10—C11—C16107.29 (18)O5—C24—H24112.2
C26—C11—C12108.41 (18)C21—C24—H24112.2
C10—C11—C12109.62 (18)C23—C24—H24112.2
C16—C11—C12106.76 (17)C17—C25—H25A109.5
C13—C12—C19113.32 (19)C17—C25—H25B109.5
C13—C12—C11109.69 (18)H25A—C25—H25B109.5
C19—C12—C11114.03 (18)C17—C25—H25C109.5
C13—C12—H12106.4H25A—C25—H25C109.5
C19—C12—H12106.4H25B—C25—H25C109.5
C11—C12—H12106.4C11—C26—H26A109.5
C27—C13—C14121.1 (2)C11—C26—H26B109.5
C27—C13—C12124.1 (2)H26A—C26—H26B109.5
C14—C13—C12114.77 (19)C11—C26—H26C109.5
C13—C14—C15111.2 (2)H26A—C26—H26C109.5
C13—C14—H14A109.4H26B—C26—H26C109.5
C15—C14—H14A109.4C13—C27—H27A120.0
C13—C14—H14B109.4C13—C27—H27B120.0
C15—C14—H14B109.4H27A—C27—H27B120.0
H14A—C14—H14B108.0
C6—C1—C2—C31.2 (4)C14—C15—C16—C1158.9 (3)
Br1—C1—C2—C3179.37 (19)C26—C11—C16—C1559.6 (3)
C1—C2—C3—C40.3 (4)C10—C11—C16—C15177.98 (19)
C2—C3—C4—C50.3 (4)C12—C11—C16—C1560.5 (2)
C3—C4—C5—C60.0 (4)C26—C11—C16—C1773.2 (3)
C2—C1—C6—C51.4 (4)C10—C11—C16—C1749.2 (3)
Br1—C1—C6—C5179.13 (17)C12—C11—C16—C17166.61 (18)
C2—C1—C6—C7179.4 (2)O1—C8—C17—C2564.0 (2)
Br1—C1—C6—C70.1 (3)C9—C8—C17—C25167.8 (2)
C4—C5—C6—C10.8 (4)O1—C8—C17—C1851.3 (2)
C4—C5—C6—C7180.0 (2)C9—C8—C17—C1876.8 (2)
C18—O2—C7—O162.6 (2)O1—C8—C17—C16176.45 (18)
C18—O2—C7—C6179.38 (18)C9—C8—C17—C1648.3 (3)
C8—O1—C7—O259.7 (2)C15—C16—C17—C8178.5 (2)
C8—O1—C7—C6179.16 (18)C11—C16—C17—C846.3 (3)
C1—C6—C7—O2163.0 (2)C15—C16—C17—C2562.8 (3)
C5—C6—C7—O217.8 (3)C11—C16—C17—C25165.0 (2)
C1—C6—C7—O176.1 (3)C15—C16—C17—C1857.2 (3)
C5—C6—C7—O1103.1 (2)C11—C16—C17—C1875.0 (3)
C7—O1—C8—C975.2 (2)C7—O2—C18—C1761.3 (2)
C7—O1—C8—C1754.3 (3)C8—C17—C18—O255.4 (2)
O1—C8—C9—C10177.19 (19)C25—C17—C18—O260.7 (3)
C17—C8—C9—C1055.5 (3)C16—C17—C18—O2177.92 (18)
C8—C9—C10—C1159.4 (3)C13—C12—C19—C2066.3 (3)
C9—C10—C11—C2670.9 (3)C11—C12—C19—C20167.3 (2)
C9—C10—C11—C1654.6 (3)C12—C19—C20—C21173.8 (2)
C9—C10—C11—C12170.1 (2)C19—C20—C21—C22178.7 (2)
C26—C11—C12—C1366.7 (2)C19—C20—C21—C240.2 (4)
C10—C11—C12—C13173.36 (18)C23—O3—C22—O4177.3 (3)
C16—C11—C12—C1357.5 (2)C23—O3—C22—C214.5 (3)
C26—C11—C12—C1961.6 (3)C20—C21—C22—O416.8 (4)
C10—C11—C12—C1958.3 (3)C24—C21—C22—O4164.2 (3)
C16—C11—C12—C19174.23 (19)C20—C21—C22—O3165.3 (2)
C19—C12—C13—C277.7 (3)C24—C21—C22—O313.8 (3)
C11—C12—C13—C27121.0 (2)C22—O3—C23—C2421.0 (3)
C19—C12—C13—C14175.03 (19)C20—C21—C24—O592.2 (3)
C11—C12—C13—C1456.3 (3)C22—C21—C24—O588.8 (2)
C27—C13—C14—C15124.2 (2)C20—C21—C24—C23154.1 (3)
C12—C13—C14—C1553.1 (3)C22—C21—C24—C2324.9 (3)
C13—C14—C15—C1652.8 (3)O3—C23—C24—O588.8 (3)
C14—C15—C16—C17166.0 (2)O3—C23—C24—C2127.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O4i0.822.202.909 (3)145
C2—H2···O5ii0.932.413.318 (4)164
Symmetry codes: (i) x, y+1/2, z+3/2; (ii) x1/2, y+1, z1/2.
 

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