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The title compound [systematic name: 2-(2,4-dihydroxy­phen­yl)-5-hydr­oxy-7-meth­oxy-6-(3-methyl-1-buten­yl)-3-(3-methyl-2-buten­yl)-4H-1-benzopyran-4-one dichoromethane hemisolvate], C26H28O6·0.5CH2Cl2, is a flavonoid isolated from Artocarpus altilis. There are two crystallographically independent mol­ecules in the asymmetric unit along with one dichloro­methane mol­ecule. In the crystal structure, inter­molecular O—H...O hydrogen bonds and weak C—H...O inter­actions link the mol­ecules into ribbons along the a axis; these ribbons are further linked into a three-dimensional network. Weak C—H...π inter­actions are also present in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011646/lh2327sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011646/lh2327Isup2.hkl
Contains datablock I

CCDC reference: 643655

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.053
  • wR factor = 0.170
  • Data-to-parameter ratio = 21.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 5 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 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

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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).

2-(2,4-dihydroxyphenyl)-5-Hydroxy-7-methoxy-6-(3-methyl-1-butenyl)- 3-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one dichoromethane hemisolvate top
Crystal data top
C26H28O6·0.5CH2Cl2Z = 4
Mr = 478.94F(000) = 1012
Triclinic, P1Dx = 1.300 Mg m3
Hall symbol: -P 1Melting point = 536–538 K
a = 8.3100 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.1722 (2) ÅCell parameters from 13015 reflections
c = 18.6940 (3) Åθ = 1.1–29.0°
α = 94.596 (1)°µ = 0.20 mm1
β = 99.104 (1)°T = 100 K
γ = 97.331 (1)°Block, yellow
V = 2447.44 (6) Å30.43 × 0.28 × 0.22 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
13015 independent reflections
Radiation source: fine-focus sealed tube9170 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 8.33 pixels mm-1θmax = 29.0°, θmin = 1.1°
ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 2122
Tmin = 0.921, Tmax = 0.959l = 2525
79612 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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.092P)2 + 0.4447P]
where P = (Fo2 + 2Fc2)/3
13015 reflections(Δ/σ)max < 0.001
614 parametersΔρmax = 0.64 e Å3
0 restraintsΔρmin = 0.49 e Å3
Special details top

Experimental. The data was 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
Cl10.98373 (7)0.01575 (3)0.20482 (3)0.04325 (15)
Cl21.02939 (12)0.19628 (4)0.19685 (4)0.0754 (3)
O1A0.65593 (14)0.63184 (7)0.12506 (6)0.0186 (2)
O2A0.95454 (16)0.40107 (7)0.12462 (6)0.0230 (3)
O3A0.70154 (15)0.48022 (7)0.09924 (6)0.0208 (3)
H3AA0.65340.51830.11430.031*
O4A0.56887 (15)0.61352 (7)0.09660 (6)0.0226 (3)
O5A0.39862 (16)0.65074 (7)0.21074 (6)0.0252 (3)
H5AA0.37720.62260.17110.038*
O6A0.46565 (16)0.93883 (7)0.29685 (6)0.0230 (3)
H6AA0.40900.91950.32540.034*
C1A0.7120 (2)0.56908 (10)0.08655 (9)0.0172 (3)
C2A0.8028 (2)0.51761 (10)0.12688 (9)0.0196 (3)
H2AA0.82400.52590.17750.024*
C3A0.8616 (2)0.45297 (10)0.08945 (9)0.0190 (3)
C4A0.8277 (2)0.43684 (10)0.01214 (9)0.0176 (3)
C5A0.7379 (2)0.49184 (10)0.02509 (9)0.0182 (3)
C6A0.6806 (2)0.55981 (10)0.01094 (8)0.0166 (3)
C7A0.5947 (2)0.61917 (10)0.02761 (8)0.0176 (3)
C8A0.5403 (2)0.68525 (10)0.01527 (9)0.0173 (3)
C9A0.5726 (2)0.68889 (10)0.08930 (9)0.0172 (3)
C10A0.5353 (2)0.75266 (10)0.14262 (9)0.0181 (3)
C11A0.4594 (2)0.73112 (10)0.20177 (9)0.0192 (3)
C12A0.4373 (2)0.79219 (10)0.25451 (9)0.0199 (3)
H12A0.38950.77700.29420.024*
C13A0.4868 (2)0.87594 (10)0.24762 (9)0.0190 (3)
C14A0.5614 (2)0.89931 (10)0.18925 (9)0.0211 (4)
H14A0.59500.95550.18500.025*
C15A0.5848 (2)0.83794 (10)0.13777 (9)0.0202 (3)
H15A0.63470.85360.09880.024*
C16A1.0233 (3)0.42394 (12)0.20002 (9)0.0278 (4)
H16A1.09650.38530.21620.042*
H16B0.93630.42230.22830.042*
H16C1.08310.47960.20600.042*
C17A0.8844 (2)0.36922 (10)0.03032 (9)0.0200 (3)
H17A0.86930.37240.08030.024*
C18A0.9541 (2)0.30400 (11)0.00788 (9)0.0217 (4)
H18A0.96970.29900.04190.026*
C19A1.0099 (2)0.23778 (11)0.05548 (9)0.0216 (4)
H19A1.13010.24390.04260.026*
C20A0.9435 (3)0.15041 (12)0.03784 (12)0.0330 (4)
H20A0.96670.14770.01380.049*
H20B0.99550.10920.06200.049*
H20C0.82670.13950.05430.049*
C21A0.9707 (2)0.24406 (12)0.13645 (10)0.0288 (4)
H21A1.01690.29830.14700.043*
H21B0.85350.23630.15180.043*
H21C1.01700.20160.16200.043*
C22A0.4564 (2)0.74900 (10)0.02499 (9)0.0191 (3)
H22A0.39360.77720.00650.023*
H22B0.38010.72080.06720.023*
C23A0.5796 (2)0.81300 (11)0.04946 (9)0.0222 (4)
H23A0.68550.79970.04820.027*
C24A0.5521 (2)0.88640 (11)0.07259 (9)0.0238 (4)
C25A0.6877 (3)0.94598 (12)0.09255 (10)0.0325 (5)
H25A0.78740.92120.08740.049*
H25B0.70440.99720.06090.049*
H25C0.65800.95760.14210.049*
C26A0.3859 (3)0.91378 (14)0.08242 (13)0.0411 (5)
H26A0.31390.87820.05880.062*
H26B0.34200.91010.13340.062*
H26C0.39490.97070.06140.062*
O1B0.75551 (15)0.06946 (7)0.38100 (6)0.0207 (3)
O2B0.89512 (16)0.20535 (8)0.37213 (6)0.0255 (3)
O3B0.77671 (16)0.08208 (8)0.59122 (6)0.0255 (3)
H3BA0.74930.03830.60730.038*
O4B0.69880 (16)0.06695 (8)0.59280 (6)0.0258 (3)
O5B0.50911 (18)0.10424 (8)0.26449 (7)0.0328 (3)
H5BA0.52220.07070.29480.049*
O6B0.61997 (17)0.39220 (8)0.23232 (7)0.0285 (3)
H6BA0.55670.37580.19410.043*
C1B0.7853 (2)0.00057 (10)0.41626 (9)0.0191 (3)
C2B0.8333 (2)0.06414 (11)0.37587 (9)0.0206 (3)
H2BA0.85030.05920.32830.025*
C3B0.8554 (2)0.13684 (10)0.40861 (9)0.0201 (3)
C4B0.8362 (2)0.14647 (10)0.48171 (9)0.0192 (3)
C5B0.7947 (2)0.07757 (11)0.52101 (9)0.0198 (3)
C6B0.7658 (2)0.00285 (10)0.48849 (8)0.0182 (3)
C7B0.7125 (2)0.06672 (10)0.52647 (9)0.0195 (3)
C8B0.6714 (2)0.13568 (10)0.48526 (9)0.0199 (3)
C9B0.6969 (2)0.13471 (10)0.41518 (9)0.0187 (3)
C10B0.6699 (2)0.19991 (10)0.36599 (9)0.0198 (3)
C11B0.5841 (2)0.18213 (11)0.29417 (9)0.0228 (4)
C12B0.5657 (2)0.24540 (11)0.24898 (9)0.0243 (4)
H12B0.50800.23280.20170.029*
C13B0.6331 (2)0.32759 (11)0.27418 (9)0.0216 (4)
C14B0.7187 (2)0.34690 (11)0.34509 (9)0.0236 (4)
H14B0.76430.40180.36210.028*
C15B0.7350 (2)0.28376 (11)0.38966 (9)0.0224 (4)
H15B0.79120.29710.43710.027*
C16B0.9241 (3)0.19929 (12)0.29906 (9)0.0301 (4)
H16D0.95510.25090.28040.045*
H16E1.01110.15420.29870.045*
H16F0.82550.18870.26900.045*
C17B0.8534 (2)0.22815 (11)0.50910 (9)0.0221 (4)
H17B0.89000.26640.47780.027*
C18B0.8251 (2)0.25581 (11)0.57135 (10)0.0242 (4)
H18B0.79620.21750.60520.029*
C19B0.8351 (2)0.34309 (11)0.59288 (10)0.0271 (4)
H19B0.92960.33950.63220.032*
C20B0.8617 (3)0.40555 (12)0.53136 (11)0.0306 (4)
H20D0.96230.38620.51490.046*
H20E0.77120.41020.49170.046*
H20F0.86830.45940.54900.046*
C21B0.6816 (3)0.37415 (13)0.62342 (12)0.0369 (5)
H21D0.66920.33490.66280.055*
H21E0.69200.42770.64090.055*
H21F0.58670.37940.58580.055*
C22B0.6023 (2)0.20529 (11)0.52316 (9)0.0212 (3)
H22C0.52370.18130.55170.025*
H22D0.54390.23540.48690.025*
C23B0.7347 (2)0.26628 (11)0.57262 (9)0.0219 (4)
H23B0.84060.25190.57950.026*
C24B0.7146 (2)0.33818 (11)0.60712 (9)0.0239 (4)
C25B0.8555 (3)0.39214 (11)0.65668 (10)0.0297 (4)
H25D0.95660.37160.65100.045*
H25E0.83920.39050.70630.045*
H25F0.86070.44880.64440.045*
C26B0.5509 (3)0.36937 (13)0.60212 (12)0.0375 (5)
H26D0.46610.32670.57610.056*
H26E0.55330.41870.57680.056*
H26F0.52860.38260.65030.056*
C271.0758 (4)0.11466 (15)0.24789 (12)0.0502 (6)
H27A1.03960.12320.29440.060*
H27B1.19430.11580.25740.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0499 (3)0.0376 (3)0.0437 (3)0.0002 (2)0.0149 (3)0.0086 (2)
Cl20.1047 (7)0.0373 (3)0.0726 (5)0.0065 (4)0.0176 (4)0.0077 (3)
O1A0.0222 (6)0.0179 (6)0.0167 (5)0.0054 (5)0.0046 (5)0.0019 (4)
O2A0.0288 (7)0.0210 (6)0.0185 (6)0.0084 (5)0.0013 (5)0.0002 (5)
O3A0.0260 (6)0.0200 (6)0.0167 (5)0.0056 (5)0.0023 (5)0.0025 (4)
O4A0.0283 (7)0.0229 (6)0.0168 (5)0.0051 (5)0.0024 (5)0.0029 (5)
O5A0.0356 (7)0.0175 (6)0.0221 (6)0.0034 (5)0.0107 (5)0.0001 (5)
O6A0.0292 (7)0.0188 (6)0.0229 (6)0.0035 (5)0.0111 (5)0.0010 (5)
C1A0.0170 (8)0.0158 (7)0.0188 (7)0.0004 (6)0.0049 (6)0.0011 (6)
C2A0.0224 (9)0.0201 (8)0.0161 (7)0.0034 (7)0.0022 (6)0.0023 (6)
C3A0.0177 (8)0.0181 (8)0.0209 (8)0.0013 (6)0.0024 (6)0.0030 (6)
C4A0.0157 (8)0.0165 (8)0.0202 (8)0.0005 (6)0.0042 (6)0.0009 (6)
C5A0.0167 (8)0.0194 (8)0.0176 (7)0.0017 (6)0.0040 (6)0.0015 (6)
C6A0.0155 (8)0.0166 (7)0.0176 (7)0.0006 (6)0.0031 (6)0.0031 (6)
C7A0.0167 (8)0.0184 (8)0.0170 (7)0.0014 (6)0.0030 (6)0.0029 (6)
C8A0.0157 (8)0.0164 (7)0.0198 (8)0.0010 (6)0.0040 (6)0.0024 (6)
C9A0.0158 (8)0.0163 (7)0.0194 (7)0.0006 (6)0.0032 (6)0.0040 (6)
C10A0.0171 (8)0.0195 (8)0.0180 (7)0.0039 (6)0.0036 (6)0.0014 (6)
C11A0.0203 (8)0.0179 (8)0.0191 (8)0.0023 (6)0.0023 (6)0.0033 (6)
C12A0.0209 (8)0.0202 (8)0.0191 (7)0.0017 (7)0.0064 (7)0.0021 (6)
C13A0.0188 (8)0.0190 (8)0.0192 (7)0.0056 (6)0.0017 (6)0.0002 (6)
C14A0.0247 (9)0.0165 (8)0.0231 (8)0.0031 (7)0.0056 (7)0.0044 (6)
C15A0.0216 (8)0.0210 (8)0.0193 (8)0.0030 (7)0.0058 (7)0.0056 (6)
C16A0.0350 (11)0.0289 (9)0.0184 (8)0.0092 (8)0.0020 (8)0.0011 (7)
C17A0.0207 (8)0.0204 (8)0.0179 (7)0.0003 (7)0.0039 (6)0.0001 (6)
C18A0.0224 (9)0.0213 (8)0.0208 (8)0.0012 (7)0.0040 (7)0.0002 (6)
C19A0.0184 (8)0.0212 (8)0.0248 (8)0.0019 (7)0.0040 (7)0.0004 (7)
C20A0.0380 (11)0.0216 (9)0.0424 (11)0.0039 (8)0.0187 (9)0.0016 (8)
C21A0.0325 (10)0.0304 (10)0.0239 (9)0.0103 (8)0.0051 (8)0.0041 (7)
C22A0.0188 (8)0.0194 (8)0.0190 (8)0.0023 (6)0.0025 (6)0.0032 (6)
C23A0.0193 (8)0.0248 (9)0.0218 (8)0.0008 (7)0.0014 (7)0.0063 (7)
C24A0.0319 (10)0.0217 (8)0.0177 (8)0.0005 (7)0.0059 (7)0.0022 (6)
C25A0.0420 (12)0.0276 (10)0.0256 (9)0.0052 (9)0.0048 (8)0.0071 (7)
C26A0.0491 (14)0.0346 (11)0.0531 (13)0.0188 (10)0.0288 (11)0.0252 (10)
O1B0.0268 (7)0.0195 (6)0.0173 (5)0.0075 (5)0.0040 (5)0.0036 (4)
O2B0.0353 (7)0.0253 (6)0.0183 (6)0.0116 (5)0.0062 (5)0.0022 (5)
O3B0.0364 (7)0.0247 (6)0.0190 (6)0.0095 (5)0.0101 (5)0.0050 (5)
O4B0.0354 (7)0.0272 (7)0.0184 (6)0.0111 (6)0.0089 (5)0.0040 (5)
O5B0.0508 (9)0.0209 (6)0.0210 (6)0.0008 (6)0.0070 (6)0.0014 (5)
O6B0.0366 (8)0.0232 (6)0.0235 (6)0.0024 (5)0.0028 (6)0.0075 (5)
C1B0.0201 (8)0.0196 (8)0.0174 (7)0.0030 (6)0.0017 (6)0.0030 (6)
C2B0.0231 (9)0.0244 (8)0.0148 (7)0.0054 (7)0.0026 (6)0.0023 (6)
C3B0.0209 (8)0.0205 (8)0.0190 (8)0.0057 (7)0.0031 (7)0.0005 (6)
C4B0.0181 (8)0.0206 (8)0.0187 (7)0.0032 (6)0.0016 (6)0.0035 (6)
C5B0.0203 (8)0.0225 (8)0.0173 (7)0.0033 (7)0.0040 (6)0.0037 (6)
C6B0.0183 (8)0.0190 (8)0.0169 (7)0.0024 (6)0.0019 (6)0.0018 (6)
C7B0.0191 (8)0.0217 (8)0.0178 (7)0.0035 (6)0.0034 (6)0.0018 (6)
C8B0.0205 (8)0.0199 (8)0.0188 (8)0.0028 (6)0.0019 (6)0.0008 (6)
C9B0.0197 (8)0.0167 (8)0.0192 (7)0.0037 (6)0.0021 (6)0.0008 (6)
C10B0.0217 (8)0.0207 (8)0.0178 (7)0.0058 (7)0.0032 (7)0.0028 (6)
C11B0.0278 (9)0.0194 (8)0.0201 (8)0.0038 (7)0.0019 (7)0.0002 (6)
C12B0.0306 (10)0.0246 (9)0.0166 (8)0.0056 (7)0.0002 (7)0.0011 (6)
C13B0.0238 (9)0.0228 (8)0.0196 (8)0.0060 (7)0.0034 (7)0.0063 (6)
C14B0.0248 (9)0.0187 (8)0.0255 (8)0.0023 (7)0.0007 (7)0.0025 (7)
C15B0.0230 (9)0.0243 (9)0.0186 (8)0.0037 (7)0.0009 (7)0.0021 (6)
C16B0.0433 (12)0.0309 (10)0.0199 (8)0.0170 (9)0.0076 (8)0.0025 (7)
C17B0.0213 (9)0.0220 (8)0.0243 (8)0.0066 (7)0.0048 (7)0.0020 (7)
C18B0.0275 (9)0.0212 (8)0.0239 (8)0.0042 (7)0.0036 (7)0.0025 (7)
C19B0.0287 (10)0.0244 (9)0.0305 (9)0.0068 (7)0.0071 (8)0.0085 (7)
C20B0.0344 (11)0.0230 (9)0.0360 (10)0.0063 (8)0.0065 (9)0.0077 (8)
C21B0.0401 (12)0.0287 (10)0.0475 (12)0.0082 (9)0.0169 (10)0.0134 (9)
C22B0.0226 (9)0.0214 (8)0.0201 (8)0.0061 (7)0.0035 (7)0.0010 (6)
C23B0.0221 (9)0.0259 (9)0.0180 (8)0.0053 (7)0.0020 (7)0.0037 (6)
C24B0.0301 (10)0.0216 (8)0.0194 (8)0.0034 (7)0.0025 (7)0.0030 (6)
C25B0.0378 (11)0.0222 (9)0.0262 (9)0.0000 (8)0.0009 (8)0.0008 (7)
C26B0.0390 (12)0.0311 (11)0.0407 (11)0.0139 (9)0.0007 (9)0.0071 (9)
C270.0625 (17)0.0497 (14)0.0319 (11)0.0008 (12)0.0055 (11)0.0045 (10)
Geometric parameters (Å, º) top
Cl1—C271.755 (2)O1B—C1B1.3688 (19)
Cl2—C271.737 (3)O1B—C9B1.371 (2)
O1A—C1A1.369 (2)O2B—C3B1.359 (2)
O1A—C9A1.376 (2)O2B—C16B1.433 (2)
O2A—C3A1.351 (2)O3B—C5B1.3511 (19)
O2A—C16A1.435 (2)O3B—H3BA0.8200
O3A—C5A1.3637 (19)O4B—C7B1.263 (2)
O3A—H3AA0.8200O5B—C11B1.364 (2)
O4A—C7A1.2675 (19)O5B—H5BA0.8200
O5A—C11A1.3666 (19)O6B—C13B1.360 (2)
O5A—H5AA0.8200O6B—H6BA0.8200
O6A—C13A1.3634 (19)C1B—C2B1.378 (2)
O6A—H6AA0.8200C1B—C6B1.390 (2)
C1A—C2A1.383 (2)C2B—C3B1.388 (2)
C1A—C6A1.389 (2)C2B—H2BA0.9300
C2A—C3A1.394 (2)C3B—C4B1.419 (2)
C2A—H2AA0.9300C4B—C5B1.395 (2)
C3A—C4A1.424 (2)C4B—C17B1.470 (2)
C4A—C5A1.392 (2)C5B—C6B1.426 (2)
C4A—C17A1.469 (2)C6B—C7B1.437 (2)
C5A—C6A1.416 (2)C7B—C8B1.451 (2)
C6A—C7A1.440 (2)C8B—C9B1.359 (2)
C7A—C8A1.445 (2)C8B—C22B1.505 (2)
C8A—C9A1.362 (2)C9B—C10B1.469 (2)
C8A—C22A1.503 (2)C10B—C15B1.403 (2)
C9A—C10A1.472 (2)C10B—C11B1.406 (2)
C10A—C15A1.402 (2)C11B—C12B1.386 (2)
C10A—C11A1.403 (2)C12B—C13B1.389 (2)
C11A—C12A1.389 (2)C12B—H12B0.9300
C12A—C13A1.387 (2)C13B—C14B1.393 (2)
C12A—H12A0.9300C14B—C15B1.375 (2)
C13A—C14A1.392 (2)C14B—H14B0.9300
C14A—C15A1.380 (2)C15B—H15B0.9300
C14A—H14A0.9300C16B—H16D0.9600
C15A—H15A0.9300C16B—H16E0.9600
C16A—H16A0.9600C16B—H16F0.9600
C16A—H16B0.9600C17B—C18B1.324 (2)
C16A—H16C0.9600C17B—H17B0.9300
C17A—C18A1.332 (2)C18B—C19B1.507 (2)
C17A—H17A0.9300C18B—H18B0.9300
C18A—C19A1.503 (2)C19B—C21B1.522 (3)
C18A—H18A0.9300C19B—C20B1.531 (3)
C19A—C21A1.511 (2)C19B—H19B0.9800
C19A—C20A1.531 (2)C20B—H20D0.9600
C19A—H19A0.9800C20B—H20E0.9600
C20A—H20A0.9600C20B—H20F0.9600
C20A—H20B0.9600C21B—H21D0.9600
C20A—H20C0.9600C21B—H21E0.9600
C21A—H21A0.9600C21B—H21F0.9600
C21A—H21B0.9600C22B—C23B1.514 (2)
C21A—H21C0.9600C22B—H22C0.9700
C22A—C23A1.511 (2)C22B—H22D0.9700
C22A—H22A0.9700C23B—C24B1.327 (2)
C22A—H22B0.9700C23B—H23B0.9300
C23A—C24A1.330 (2)C24B—C26B1.502 (3)
C23A—H23A0.9300C24B—C25B1.503 (2)
C24A—C26A1.492 (3)C25B—H25D0.9600
C24A—C25A1.500 (3)C25B—H25E0.9600
C25A—H25A0.9600C25B—H25F0.9600
C25A—H25B0.9600C26B—H26D0.9600
C25A—H25C0.9600C26B—H26E0.9600
C26A—H26A0.9600C26B—H26F0.9600
C26A—H26B0.9600C27—H27A0.9700
C26A—H26C0.9600C27—H27B0.9700
C1A—O1A—C9A120.38 (12)C11B—O5B—H5BA109.5
C3A—O2A—C16A118.53 (13)C13B—O6B—H6BA109.5
C5A—O3A—H3AA109.5O1B—C1B—C2B116.18 (14)
C11A—O5A—H5AA109.5O1B—C1B—C6B120.93 (15)
C13A—O6A—H6AA109.5C2B—C1B—C6B122.88 (16)
O1A—C1A—C2A116.49 (14)C1B—C2B—C3B117.70 (15)
O1A—C1A—C6A120.82 (15)C1B—C2B—H2BA121.1
C2A—C1A—C6A122.68 (15)C3B—C2B—H2BA121.1
C1A—C2A—C3A118.03 (15)O2B—C3B—C2B122.01 (15)
C1A—C2A—H2AA121.0O2B—C3B—C4B114.64 (15)
C3A—C2A—H2AA121.0C2B—C3B—C4B123.34 (15)
O2A—C3A—C2A121.81 (14)C5B—C4B—C3B116.42 (15)
O2A—C3A—C4A115.58 (14)C5B—C4B—C17B125.12 (15)
C2A—C3A—C4A122.61 (15)C3B—C4B—C17B118.39 (15)
C5A—C4A—C3A116.29 (15)O3B—C5B—C4B119.52 (15)
C5A—C4A—C17A118.51 (14)O3B—C5B—C6B118.67 (15)
C3A—C4A—C17A125.16 (15)C4B—C5B—C6B121.79 (15)
O3A—C5A—C4A119.36 (15)C1B—C6B—C5B117.76 (15)
O3A—C5A—C6A117.97 (14)C1B—C6B—C7B119.48 (15)
C4A—C5A—C6A122.67 (14)C5B—C6B—C7B122.72 (15)
C1A—C6A—C5A117.61 (15)O4B—C7B—C6B121.18 (15)
C1A—C6A—C7A119.68 (15)O4B—C7B—C8B121.34 (15)
C5A—C6A—C7A122.71 (14)C6B—C7B—C8B117.46 (14)
O4A—C7A—C6A120.88 (15)C9B—C8B—C7B119.12 (15)
O4A—C7A—C8A121.57 (15)C9B—C8B—C22B123.30 (15)
C6A—C7A—C8A117.55 (14)C7B—C8B—C22B117.59 (14)
C9A—C8A—C7A119.20 (15)C8B—C9B—O1B122.35 (15)
C9A—C8A—C22A123.30 (15)C8B—C9B—C10B127.15 (15)
C7A—C8A—C22A117.46 (14)O1B—C9B—C10B110.50 (13)
C8A—C9A—O1A122.32 (15)C15B—C10B—C11B117.34 (15)
C8A—C9A—C10A127.85 (15)C15B—C10B—C9B119.81 (14)
O1A—C9A—C10A109.77 (13)C11B—C10B—C9B122.83 (15)
C15A—C10A—C11A117.76 (15)O5B—C11B—C12B115.17 (15)
C15A—C10A—C9A120.03 (14)O5B—C11B—C10B123.94 (15)
C11A—C10A—C9A122.10 (14)C12B—C11B—C10B120.85 (15)
O5A—C11A—C12A115.57 (14)C11B—C12B—C13B120.14 (15)
O5A—C11A—C10A123.38 (15)C11B—C12B—H12B119.9
C12A—C11A—C10A121.03 (15)C13B—C12B—H12B119.9
C13A—C12A—C11A119.55 (15)O6B—C13B—C12B122.85 (15)
C13A—C12A—H12A120.2O6B—C13B—C14B116.99 (15)
C11A—C12A—H12A120.2C12B—C13B—C14B120.16 (15)
O6A—C13A—C12A122.32 (15)C15B—C14B—C13B119.22 (15)
O6A—C13A—C14A116.95 (14)C15B—C14B—H14B120.4
C12A—C13A—C14A120.74 (15)C13B—C14B—H14B120.4
C15A—C14A—C13A119.13 (15)C14B—C15B—C10B122.28 (15)
C15A—C14A—H14A120.4C14B—C15B—H15B118.9
C13A—C14A—H14A120.4C10B—C15B—H15B118.9
C14A—C15A—C10A121.78 (15)O2B—C16B—H16D109.5
C14A—C15A—H15A119.1O2B—C16B—H16E109.5
C10A—C15A—H15A119.1H16D—C16B—H16E109.5
O2A—C16A—H16A109.5O2B—C16B—H16F109.5
O2A—C16A—H16B109.5H16D—C16B—H16F109.5
H16A—C16A—H16B109.5H16E—C16B—H16F109.5
O2A—C16A—H16C109.5C18B—C17B—C4B130.18 (17)
H16A—C16A—H16C109.5C18B—C17B—H17B114.9
H16B—C16A—H16C109.5C4B—C17B—H17B114.9
C18A—C17A—C4A129.66 (15)C17B—C18B—C19B126.55 (17)
C18A—C17A—H17A115.2C17B—C18B—H18B116.7
C4A—C17A—H17A115.2C19B—C18B—H18B116.7
C17A—C18A—C19A126.06 (16)C18B—C19B—C21B109.43 (16)
C17A—C18A—H18A117.0C18B—C19B—C20B113.91 (15)
C19A—C18A—H18A117.0C21B—C19B—C20B110.96 (16)
C18A—C19A—C21A115.55 (15)C18B—C19B—H19B107.4
C18A—C19A—C20A110.31 (14)C21B—C19B—H19B107.4
C21A—C19A—C20A110.34 (15)C20B—C19B—H19B107.4
C18A—C19A—H19A106.7C19B—C20B—H20D109.5
C21A—C19A—H19A106.7C19B—C20B—H20E109.5
C20A—C19A—H19A106.7H20D—C20B—H20E109.5
C19A—C20A—H20A109.5C19B—C20B—H20F109.5
C19A—C20A—H20B109.5H20D—C20B—H20F109.5
H20A—C20A—H20B109.5H20E—C20B—H20F109.5
C19A—C20A—H20C109.5C19B—C21B—H21D109.5
H20A—C20A—H20C109.5C19B—C21B—H21E109.5
H20B—C20A—H20C109.5H21D—C21B—H21E109.5
C19A—C21A—H21A109.5C19B—C21B—H21F109.5
C19A—C21A—H21B109.5H21D—C21B—H21F109.5
H21A—C21A—H21B109.5H21E—C21B—H21F109.5
C19A—C21A—H21C109.5C8B—C22B—C23B112.42 (15)
H21A—C21A—H21C109.5C8B—C22B—H22C109.1
H21B—C21A—H21C109.5C23B—C22B—H22C109.1
C8A—C22A—C23A111.33 (14)C8B—C22B—H22D109.1
C8A—C22A—H22A109.4C23B—C22B—H22D109.1
C23A—C22A—H22A109.4H22C—C22B—H22D107.9
C8A—C22A—H22B109.4C24B—C23B—C22B126.39 (17)
C23A—C22A—H22B109.4C24B—C23B—H23B116.8
H22A—C22A—H22B108.0C22B—C23B—H23B116.8
C24A—C23A—C22A126.71 (17)C23B—C24B—C26B123.02 (17)
C24A—C23A—H23A116.6C23B—C24B—C25B121.27 (17)
C22A—C23A—H23A116.6C26B—C24B—C25B115.67 (16)
C23A—C24A—C26A122.77 (17)C24B—C25B—H25D109.5
C23A—C24A—C25A121.36 (18)C24B—C25B—H25E109.5
C26A—C24A—C25A115.85 (16)H25D—C25B—H25E109.5
C24A—C25A—H25A109.5C24B—C25B—H25F109.5
C24A—C25A—H25B109.5H25D—C25B—H25F109.5
H25A—C25A—H25B109.5H25E—C25B—H25F109.5
C24A—C25A—H25C109.5C24B—C26B—H26D109.5
H25A—C25A—H25C109.5C24B—C26B—H26E109.5
H25B—C25A—H25C109.5H26D—C26B—H26E109.5
C24A—C26A—H26A109.5C24B—C26B—H26F109.5
C24A—C26A—H26B109.5H26D—C26B—H26F109.5
H26A—C26A—H26B109.5H26E—C26B—H26F109.5
C24A—C26A—H26C109.5Cl2—C27—Cl1113.18 (13)
H26A—C26A—H26C109.5Cl2—C27—H27A108.9
H26B—C26A—H26C109.5Cl1—C27—H27A108.9
C1B—O1B—C9B120.42 (13)Cl2—C27—H27B108.9
C3B—O2B—C16B118.00 (14)Cl1—C27—H27B108.9
C5B—O3B—H3BA109.5H27A—C27—H27B107.8
C9A—O1A—C1A—C2A176.31 (14)C9B—O1B—C1B—C2B175.74 (15)
C9A—O1A—C1A—C6A2.5 (2)C9B—O1B—C1B—C6B3.6 (2)
O1A—C1A—C2A—C3A179.91 (14)O1B—C1B—C2B—C3B176.38 (15)
C6A—C1A—C2A—C3A1.3 (2)C6B—C1B—C2B—C3B3.0 (3)
C16A—O2A—C3A—C2A13.6 (2)C16B—O2B—C3B—C2B3.7 (2)
C16A—O2A—C3A—C4A166.67 (15)C16B—O2B—C3B—C4B177.15 (15)
C1A—C2A—C3A—O2A178.43 (15)C1B—C2B—C3B—O2B176.91 (16)
C1A—C2A—C3A—C4A1.9 (2)C1B—C2B—C3B—C4B2.1 (3)
O2A—C3A—C4A—C5A177.44 (14)O2B—C3B—C4B—C5B179.77 (14)
C2A—C3A—C4A—C5A2.9 (2)C2B—C3B—C4B—C5B0.7 (3)
O2A—C3A—C4A—C17A0.5 (2)O2B—C3B—C4B—C17B2.6 (2)
C2A—C3A—C4A—C17A179.23 (15)C2B—C3B—C4B—C17B176.52 (16)
C3A—C4A—C5A—O3A179.76 (13)C3B—C4B—C5B—O3B179.14 (15)
C17A—C4A—C5A—O3A1.7 (2)C17B—C4B—C5B—O3B3.9 (3)
C3A—C4A—C5A—C6A0.7 (2)C3B—C4B—C5B—C6B2.7 (2)
C17A—C4A—C5A—C6A178.81 (14)C17B—C4B—C5B—C6B174.23 (16)
O1A—C1A—C6A—C5A178.00 (13)O1B—C1B—C6B—C5B178.32 (14)
C2A—C1A—C6A—C5A3.3 (2)C2B—C1B—C6B—C5B1.0 (3)
O1A—C1A—C6A—C7A2.9 (2)O1B—C1B—C6B—C7B0.4 (2)
C2A—C1A—C6A—C7A175.78 (15)C2B—C1B—C6B—C7B178.90 (15)
O3A—C5A—C6A—C1A177.31 (14)O3B—C5B—C6B—C1B179.89 (15)
C4A—C5A—C6A—C1A2.2 (2)C4B—C5B—C6B—C1B2.0 (2)
O3A—C5A—C6A—C7A3.7 (2)O3B—C5B—C6B—C7B2.3 (2)
C4A—C5A—C6A—C7A176.85 (15)C4B—C5B—C6B—C7B175.83 (16)
C1A—C6A—C7A—O4A177.88 (15)C1B—C6B—C7B—O4B177.61 (16)
C5A—C6A—C7A—O4A1.1 (2)C5B—C6B—C7B—O4B4.6 (3)
C1A—C6A—C7A—C8A1.8 (2)C1B—C6B—C7B—C8B3.8 (2)
C5A—C6A—C7A—C8A179.18 (14)C5B—C6B—C7B—C8B173.95 (15)
O4A—C7A—C8A—C9A179.41 (15)O4B—C7B—C8B—C9B176.38 (16)
C6A—C7A—C8A—C9A0.3 (2)C6B—C7B—C8B—C9B5.1 (2)
O4A—C7A—C8A—C22A1.9 (2)O4B—C7B—C8B—C22B3.5 (2)
C6A—C7A—C8A—C22A177.77 (14)C6B—C7B—C8B—C22B175.07 (14)
C7A—C8A—C9A—O1A0.2 (2)C7B—C8B—C9B—O1B2.1 (2)
C22A—C8A—C9A—O1A177.15 (14)C22B—C8B—C9B—O1B178.06 (15)
C7A—C8A—C9A—C10A176.90 (15)C7B—C8B—C9B—C10B177.18 (16)
C22A—C8A—C9A—C10A0.4 (3)C22B—C8B—C9B—C10B2.7 (3)
C1A—O1A—C9A—C8A0.9 (2)C1B—O1B—C9B—C8B2.4 (2)
C1A—O1A—C9A—C10A176.35 (13)C1B—O1B—C9B—C10B178.27 (13)
C8A—C9A—C10A—C15A51.7 (2)C8B—C9B—C10B—C15B49.6 (3)
O1A—C9A—C10A—C15A125.35 (16)O1B—C9B—C10B—C15B129.71 (17)
C8A—C9A—C10A—C11A132.19 (18)C8B—C9B—C10B—C11B132.1 (2)
O1A—C9A—C10A—C11A50.8 (2)O1B—C9B—C10B—C11B48.5 (2)
C15A—C10A—C11A—O5A176.73 (16)C15B—C10B—C11B—O5B177.56 (17)
C9A—C10A—C11A—O5A7.1 (3)C9B—C10B—C11B—O5B4.2 (3)
C15A—C10A—C11A—C12A1.3 (2)C15B—C10B—C11B—C12B0.2 (3)
C9A—C10A—C11A—C12A174.87 (15)C9B—C10B—C11B—C12B178.12 (17)
O5A—C11A—C12A—C13A176.42 (15)O5B—C11B—C12B—C13B178.27 (17)
C10A—C11A—C12A—C13A1.8 (3)C10B—C11B—C12B—C13B0.4 (3)
C11A—C12A—C13A—O6A178.79 (15)C11B—C12B—C13B—O6B179.59 (17)
C11A—C12A—C13A—C14A1.3 (3)C11B—C12B—C13B—C14B0.3 (3)
O6A—C13A—C14A—C15A179.69 (15)O6B—C13B—C14B—C15B179.86 (16)
C12A—C13A—C14A—C15A0.4 (3)C12B—C13B—C14B—C15B0.2 (3)
C13A—C14A—C15A—C10A0.1 (3)C13B—C14B—C15B—C10B0.8 (3)
C11A—C10A—C15A—C14A0.4 (3)C11B—C10B—C15B—C14B0.7 (3)
C9A—C10A—C15A—C14A175.88 (16)C9B—C10B—C15B—C14B177.61 (17)
C5A—C4A—C17A—C18A171.25 (17)C5B—C4B—C17B—C18B4.8 (3)
C3A—C4A—C17A—C18A10.9 (3)C3B—C4B—C17B—C18B172.17 (19)
C4A—C17A—C18A—C19A179.44 (16)C4B—C17B—C18B—C19B175.46 (18)
C17A—C18A—C19A—C21A4.6 (3)C17B—C18B—C19B—C21B132.2 (2)
C17A—C18A—C19A—C20A130.56 (19)C17B—C18B—C19B—C20B7.3 (3)
C9A—C8A—C22A—C23A98.86 (19)C9B—C8B—C22B—C23B100.35 (19)
C7A—C8A—C22A—C23A78.52 (18)C7B—C8B—C22B—C23B79.52 (19)
C8A—C22A—C23A—C24A165.11 (17)C8B—C22B—C23B—C24B172.49 (16)
C22A—C23A—C24A—C26A4.3 (3)C22B—C23B—C24B—C26B0.7 (3)
C22A—C23A—C24A—C25A177.48 (16)C22B—C23B—C24B—C25B178.12 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3A—H3AA···O4A0.821.802.5440 (17)150
O5A—H5AA···O1A0.822.592.8988 (17)104
O5A—H5AA···O3Ai0.822.022.7958 (16)158
O6A—H6AA···O4Bii0.821.902.6499 (17)151
O3B—H3BA···O4B0.821.842.5733 (18)149
O5B—H5BA···O1B0.822.322.8865 (18)127
O5B—H5BA···O6Aiii0.822.132.7810 (17)136
O6B—H6BA···O4Ai0.821.982.7520 (17)156
C17A—H17A···O3A0.932.382.764 (2)104
C17B—H17B···O2B0.932.282.686 (2)106
C18A—H18A···O2A0.932.202.824 (2)124
C18B—H18B···O3B0.932.252.892 (2)126
C23B—H23B···O2Biv0.932.473.381 (2)166
C25A—H25C···O5Bi0.962.543.353 (2)143
C16B—H16F···Cg3iii0.962.763.709 (2)168
C19A—H19A···Cg1v0.982.763.4928 (18)132
C21A—H21B···Cg3i0.963.003.9497 (19)172
C21B—H21D···Cg4vi0.963.083.717 (3)125
C22B—H22C···Cg2vi0.973.113.9588 (19)147
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+1, z+1; (iii) x, y1, z; (iv) x+2, y, z+1; (v) x+2, y+1, z; (vi) x+1, y, z+1.
 

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