Diethyl 2,5-bis­(3,4,5-trimethoxy­phenyl)furan-3,4-dicarboxyl­ate 0.16-hydrate

In the title compound, C₂₈H₃₂O₁₁·0.16H₂O, the substituted benzene rings are twisted slightly away from the furan ring. The dihedral angle between the two benzene rings is 8.8 (1)°. In the crystal structure, the mol­ecules exist as C—H...O hydrogen-bonded dimers.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.004 Å
• H-atom completeness 100%
• Disorder in main residue
• R factor = 0.064
• wR factor = 0.180
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O2     ..  O12     ..       2.78 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.20 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.35 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C26
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C27'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C27
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      16.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....       <O12

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C28 H32.32 O11.16
            Atom count from the _atom_site data:  C28 H32 O11.16
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C28 H32.32 O11.16
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        112.00    112.00    0.00
           H        129.28    128.00    1.28
           O         44.64     44.64    0.00

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Diethyl 2,5-bis(3,4,5-trimethoxyphenyl)furan-3,4-dicarboxylate 0.16-hydrate

Crystal data

C28H32O11·0.16H2O	F(000) = 1158
Mr = 547.42	Dx = 1.348 Mg m^−3
Monoclinic, P21/n	Melting point: 99 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.4402 (7) Å	Cell parameters from 2494 reflections
b = 22.1502 (19) Å	θ = 2.7–23.8°
c = 14.5043 (12) Å	µ = 0.11 mm^−1
β = 95.835 (2)°	T = 292 K
V = 2697.6 (4) Å^3	Block, colourless
Z = 4	0.50 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	5270 independent reflections
Radiation source: fine-focus sealed tube	3426 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.949, Tmax = 0.979	k = −27→25
14583 measured reflections	l = −16→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.180	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0817P)^2 + 0.3534P] where P = (Fo^2 + 2Fc^2)/3
5270 reflections	(Δ/σ)max = 0.001
389 parameters	Δρmax = 0.23 e Å^−3
4 restraints	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.5932 (3)	0.98670 (13)	0.79491 (17)	0.0482 (7)
C2	0.5775 (3)	1.04782 (13)	0.81169 (18)	0.0536 (8)
C3	0.4824 (3)	1.08288 (12)	0.74931 (18)	0.0498 (7)
C4	0.4028 (3)	1.05710 (12)	0.67128 (18)	0.0478 (7)
H4	0.3371	1.0807	0.6305	0.057*
C5	0.4204 (3)	0.99602 (11)	0.65342 (16)	0.0392 (6)
C6	0.5158 (3)	0.96049 (12)	0.71583 (17)	0.0456 (7)
H6	0.5276	0.9195	0.7046	0.055*
C7	0.7055 (4)	0.89323 (14)	0.8503 (2)	0.0661 (9)
H7A	0.6054	0.8739	0.8568	0.099*
H7B	0.7846	0.8784	0.8971	0.099*
H7C	0.7376	0.8846	0.7901	0.099*
C8	0.5819 (6)	1.0850 (2)	0.9639 (2)	0.1207 (18)
H8A	0.4964	1.1126	0.9468	0.181*
H8B	0.6532	1.1023	1.0126	0.181*
H8C	0.5393	1.0479	0.9852	0.181*
C9	0.4006 (4)	1.18221 (13)	0.7042 (2)	0.0768 (11)
H9A	0.4488	1.1774	0.6475	0.115*
H9B	0.4141	1.2231	0.7255	0.115*
H9C	0.2891	1.1731	0.6936	0.115*
C10	0.3338 (3)	0.97104 (11)	0.56840 (16)	0.0381 (6)
C11	0.3005 (3)	0.91598 (11)	0.52696 (16)	0.0393 (6)
C12	0.1944 (3)	0.92798 (11)	0.44451 (16)	0.0389 (6)
C13	0.1729 (3)	0.98809 (11)	0.43940 (16)	0.0378 (6)
C14	0.0899 (3)	1.03036 (11)	0.37345 (17)	0.0410 (6)
C15	0.0162 (3)	1.01051 (13)	0.28898 (18)	0.0516 (7)
H15	0.0143	0.9695	0.2749	0.062*
C16	−0.0545 (4)	1.05162 (14)	0.22576 (18)	0.0535 (7)
C17	−0.0515 (3)	1.11275 (13)	0.24669 (18)	0.0508 (7)
C18	0.0215 (3)	1.13257 (12)	0.33107 (19)	0.0490 (7)
C19	0.0922 (3)	1.09151 (12)	0.39452 (17)	0.0452 (7)
H19	0.1411	1.1049	0.4512	0.054*
C20	−0.1133 (5)	0.97652 (17)	0.1104 (2)	0.0907 (13)
H20A	−0.0032	0.9651	0.1134	0.136*
H20B	−0.1615	0.9727	0.0479	0.136*
H20C	−0.1673	0.9507	0.1502	0.136*
C21	−0.2687 (4)	1.16817 (17)	0.1789 (2)	0.0797 (11)
H21A	−0.3296	1.1315	0.1742	0.120*
H21B	−0.3010	1.1936	0.1268	0.120*
H21C	−0.2867	1.1888	0.2352	0.120*
C22	0.1191 (4)	1.21677 (14)	0.4222 (2)	0.0737 (10)
H22A	0.0780	1.2039	0.4783	0.111*
H22B	0.1196	1.2601	0.4196	0.111*
H22C	0.2257	1.2019	0.4210	0.111*
C23	0.1129 (4)	0.88253 (12)	0.38017 (17)	0.0449 (7)
C24	0.1304 (5)	0.82479 (15)	0.2438 (2)	0.0760 (10)
H24A	0.1809	0.8297	0.1871	0.091*
H24B	0.0182	0.8343	0.2304	0.091*
C25	0.1481 (5)	0.76137 (16)	0.2759 (2)	0.0883 (12)
H25A	0.2582	0.7533	0.2953	0.132*
H25B	0.1115	0.7347	0.2261	0.132*
H25C	0.0862	0.7551	0.3270	0.132*
C26	0.3589 (4)	0.85588 (12)	0.55658 (19)	0.0530 (7)
C27	0.2935 (11)	0.7505 (3)	0.5429 (7)	0.060 (3)	0.467 (12)
H27A	0.1985	0.7280	0.5210	0.071*	0.467 (12)
H27B	0.3048	0.7508	0.6101	0.071*	0.467 (12)
C28	0.4375 (10)	0.7242 (5)	0.5063 (5)	0.074 (3)	0.467 (12)
H28A	0.4277	0.7277	0.4400	0.110*	0.467 (12)
H28B	0.4468	0.6824	0.5234	0.110*	0.467 (12)
H28C	0.5306	0.7455	0.5321	0.110*	0.467 (12)
C27'	0.3727 (11)	0.7545 (3)	0.5108 (6)	0.071 (3)	0.533 (12)
H27C	0.4776	0.7586	0.5444	0.085*	0.533 (12)
H27D	0.3838	0.7386	0.4495	0.085*	0.533 (12)
C28'	0.2687 (11)	0.7153 (6)	0.5617 (6)	0.105 (3)	0.533 (12)
H28D	0.2604	0.7319	0.6222	0.158*	0.533 (12)
H28E	0.3137	0.6755	0.5677	0.158*	0.533 (12)
H28F	0.1648	0.7132	0.5282	0.158*	0.533 (12)
O1	0.6889 (3)	0.95594 (10)	0.86066 (13)	0.0682 (6)
O2	0.6644 (3)	1.07344 (10)	0.88719 (15)	0.0795 (7)
O3	0.4741 (3)	1.14250 (9)	0.77218 (14)	0.0682 (6)
O4	0.2574 (2)	1.01462 (7)	0.51448 (11)	0.0415 (4)
O5	−0.1250 (3)	1.03710 (11)	0.13980 (14)	0.0796 (7)
O6	−0.1068 (3)	1.15451 (10)	0.17984 (14)	0.0693 (6)
O7	0.0212 (3)	1.19369 (9)	0.34460 (14)	0.0670 (6)
O8	−0.0213 (3)	0.86536 (10)	0.38455 (14)	0.0672 (6)
O9	0.2030 (3)	0.86633 (9)	0.31456 (13)	0.0648 (6)
O10	0.4587 (3)	0.84448 (10)	0.61832 (17)	0.0965 (9)
O11	0.2865 (3)	0.81276 (9)	0.50560 (17)	0.0896 (9)
O12	0.5861 (17)	0.6377 (7)	0.5183 (8)	0.076 (4)	0.16

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0519 (17)	0.0528 (17)	0.0370 (14)	0.0005 (13)	−0.0089 (12)	0.0025 (12)
C2	0.0578 (19)	0.0563 (19)	0.0431 (16)	−0.0074 (14)	−0.0120 (14)	−0.0084 (13)
C3	0.0581 (18)	0.0408 (16)	0.0481 (15)	−0.0024 (13)	−0.0057 (14)	−0.0113 (13)
C4	0.0566 (18)	0.0415 (16)	0.0421 (15)	−0.0005 (13)	−0.0099 (13)	−0.0016 (12)
C5	0.0435 (15)	0.0381 (14)	0.0350 (13)	−0.0037 (11)	−0.0017 (11)	−0.0009 (11)
C6	0.0538 (17)	0.0387 (15)	0.0423 (14)	−0.0013 (12)	−0.0056 (13)	−0.0014 (11)
C7	0.070 (2)	0.062 (2)	0.0631 (19)	0.0075 (16)	−0.0088 (16)	0.0110 (16)
C8	0.187 (5)	0.119 (4)	0.050 (2)	0.029 (3)	−0.019 (3)	−0.027 (2)
C9	0.088 (3)	0.0385 (17)	0.096 (3)	0.0003 (16)	−0.029 (2)	−0.0122 (17)
C10	0.0448 (15)	0.0331 (13)	0.0353 (13)	0.0017 (11)	−0.0013 (11)	0.0027 (10)
C11	0.0418 (15)	0.0369 (14)	0.0376 (13)	0.0004 (11)	−0.0039 (11)	0.0006 (11)
C12	0.0417 (15)	0.0391 (14)	0.0347 (13)	−0.0028 (11)	−0.0014 (11)	−0.0004 (11)
C13	0.0434 (15)	0.0374 (14)	0.0307 (12)	−0.0033 (11)	−0.0050 (11)	−0.0022 (10)
C14	0.0445 (15)	0.0405 (15)	0.0372 (13)	−0.0002 (11)	0.0001 (11)	0.0035 (11)
C15	0.0644 (19)	0.0438 (16)	0.0434 (15)	−0.0013 (13)	−0.0096 (14)	−0.0007 (12)
C16	0.0585 (19)	0.0616 (19)	0.0369 (15)	0.0022 (15)	−0.0115 (13)	0.0039 (13)
C17	0.0510 (17)	0.0564 (18)	0.0433 (15)	0.0049 (14)	−0.0036 (13)	0.0145 (13)
C18	0.0540 (17)	0.0411 (16)	0.0521 (16)	0.0050 (13)	0.0066 (14)	0.0084 (12)
C19	0.0498 (17)	0.0431 (16)	0.0416 (14)	0.0038 (12)	−0.0011 (12)	0.0014 (12)
C20	0.123 (3)	0.084 (3)	0.057 (2)	0.001 (2)	−0.033 (2)	−0.0167 (18)
C21	0.067 (2)	0.083 (3)	0.083 (2)	0.0085 (19)	−0.0204 (19)	0.0105 (19)
C22	0.091 (3)	0.0452 (19)	0.083 (2)	−0.0065 (17)	−0.003 (2)	0.0017 (16)
C23	0.0538 (18)	0.0381 (15)	0.0408 (15)	−0.0012 (13)	−0.0047 (13)	−0.0008 (11)
C24	0.103 (3)	0.068 (2)	0.0562 (19)	−0.023 (2)	0.0036 (18)	−0.0236 (16)
C25	0.114 (3)	0.063 (2)	0.084 (3)	−0.019 (2)	−0.007 (2)	−0.0256 (19)
C26	0.068 (2)	0.0407 (16)	0.0456 (15)	0.0073 (14)	−0.0155 (14)	−0.0055 (12)
C27	0.057 (6)	0.047 (6)	0.075 (6)	0.000 (5)	0.009 (4)	0.007 (5)
C28	0.094 (7)	0.052 (6)	0.069 (5)	0.007 (5)	−0.019 (5)	−0.016 (4)
C27'	0.080 (7)	0.041 (5)	0.088 (6)	0.009 (6)	−0.015 (5)	−0.014 (5)
C28'	0.131 (8)	0.068 (7)	0.116 (7)	−0.002 (6)	0.010 (6)	0.021 (5)
O1	0.0853 (16)	0.0610 (14)	0.0513 (12)	0.0076 (11)	−0.0270 (11)	0.0027 (10)
O2	0.0906 (18)	0.0776 (16)	0.0622 (14)	−0.0047 (13)	−0.0312 (13)	−0.0228 (12)
O3	0.0909 (17)	0.0439 (12)	0.0640 (13)	0.0039 (11)	−0.0204 (12)	−0.0165 (10)
O4	0.0521 (11)	0.0336 (10)	0.0360 (9)	−0.0006 (8)	−0.0092 (8)	0.0005 (7)
O5	0.1030 (19)	0.0786 (17)	0.0492 (12)	0.0088 (14)	−0.0317 (12)	−0.0010 (11)
O6	0.0738 (16)	0.0721 (15)	0.0602 (13)	0.0155 (12)	−0.0020 (11)	0.0259 (11)
O7	0.0901 (16)	0.0411 (12)	0.0667 (13)	0.0087 (11)	−0.0078 (12)	0.0086 (10)
O8	0.0538 (13)	0.0713 (15)	0.0751 (14)	−0.0174 (11)	−0.0001 (11)	−0.0200 (11)
O9	0.0752 (15)	0.0632 (14)	0.0570 (12)	−0.0202 (11)	0.0117 (11)	−0.0258 (10)
O10	0.137 (2)	0.0487 (13)	0.0886 (17)	0.0238 (14)	−0.0644 (16)	−0.0148 (12)
O11	0.123 (2)	0.0331 (12)	0.0991 (17)	0.0072 (12)	−0.0566 (16)	−0.0068 (11)
O12	0.089 (10)	0.089 (11)	0.051 (7)	0.038 (8)	0.009 (7)	−0.008 (7)

Geometric parameters (Å, º)

C1—O1	1.367 (3)	C18—O7	1.368 (3)
C1—C2	1.384 (4)	C18—C19	1.385 (3)
C1—C6	1.388 (3)	C19—H19	0.93
C2—O2	1.377 (3)	C20—O5	1.414 (4)
C2—C3	1.385 (4)	C20—H20A	0.96
C3—O3	1.365 (3)	C20—H20B	0.96
C3—C4	1.380 (3)	C20—H20C	0.96
C4—C5	1.388 (4)	C21—O6	1.398 (4)
C4—H4	0.93	C21—H21A	0.96
C5—C6	1.393 (3)	C21—H21B	0.96
C5—C10	1.476 (3)	C21—H21C	0.96
C6—H6	0.93	C22—O7	1.421 (4)
C7—O1	1.406 (4)	C22—H22A	0.96
C7—H7A	0.96	C22—H22B	0.96
C7—H7B	0.96	C22—H22C	0.96
C7—H7C	0.96	C23—O8	1.202 (3)
C8—O2	1.395 (5)	C23—O9	1.327 (3)
C8—H8A	0.96	C24—O9	1.466 (3)
C8—H8B	0.96	C24—C25	1.483 (5)
C8—H8C	0.96	C24—H24A	0.97
C9—O3	1.416 (4)	C24—H24B	0.97
C9—H9A	0.96	C25—H25A	0.96
C9—H9B	0.96	C25—H25B	0.96
C9—H9C	0.96	C25—H25C	0.96
C10—O4	1.363 (3)	C26—O10	1.193 (3)
C10—C11	1.376 (3)	C26—O11	1.319 (3)
C11—C12	1.444 (3)	C27—O11	1.480 (7)
C11—C26	1.468 (4)	C27—C28	1.493 (8)
C12—C13	1.345 (3)	C27—H27A	0.97
C12—C23	1.492 (3)	C27—H27B	0.97
C13—O4	1.372 (3)	C28—H28A	0.96
C13—C14	1.465 (3)	C28—H28B	0.96
C14—C15	1.388 (3)	C28—H28C	0.96
C14—C19	1.388 (3)	C27'—O11	1.480 (7)
C15—C16	1.384 (4)	C27'—C28'	1.483 (8)
C15—H15	0.93	C27'—H27C	0.97
C16—O5	1.364 (3)	C27'—H27D	0.97
C16—C17	1.387 (4)	C28'—H28D	0.96
C17—C18	1.385 (4)	C28'—H28E	0.96
C17—O6	1.386 (3)	C28'—H28F	0.96
O1—C1—C2	115.2 (2)	C14—C19—H19	120.0
O1—C1—C6	124.3 (3)	O5—C20—H20A	109.5
C2—C1—C6	120.6 (2)	O5—C20—H20B	109.5
O2—C2—C1	119.3 (2)	H20A—C20—H20B	109.5
O2—C2—C3	121.0 (3)	O5—C20—H20C	109.5
C1—C2—C3	119.5 (2)	H20A—C20—H20C	109.5
O3—C3—C4	124.5 (2)	H20B—C20—H20C	109.5
O3—C3—C2	115.1 (2)	O6—C21—H21A	109.5
C4—C3—C2	120.4 (3)	O6—C21—H21B	109.5
C3—C4—C5	120.3 (2)	H21A—C21—H21B	109.5
C3—C4—H4	119.9	O6—C21—H21C	109.5
C5—C4—H4	119.9	H21A—C21—H21C	109.5
C4—C5—C6	119.7 (2)	H21B—C21—H21C	109.5
C4—C5—C10	117.9 (2)	O7—C22—H22A	109.5
C6—C5—C10	122.4 (2)	O7—C22—H22B	109.5
C1—C6—C5	119.6 (2)	H22A—C22—H22B	109.5
C1—C6—H6	120.2	O7—C22—H22C	109.5
C5—C6—H6	120.2	H22A—C22—H22C	109.5
O1—C7—H7A	109.5	H22B—C22—H22C	109.5
O1—C7—H7B	109.5	O8—C23—O9	124.3 (2)
H7A—C7—H7B	109.5	O8—C23—C12	123.8 (3)
O1—C7—H7C	109.5	O9—C23—C12	111.7 (2)
H7A—C7—H7C	109.5	O9—C24—C25	110.7 (3)
H7B—C7—H7C	109.5	O9—C24—H24A	109.5
O2—C8—H8A	109.5	C25—C24—H24A	109.5
O2—C8—H8B	109.5	O9—C24—H24B	109.5
H8A—C8—H8B	109.5	C25—C24—H24B	109.5
O2—C8—H8C	109.5	H24A—C24—H24B	108.1
H8A—C8—H8C	109.5	C24—C25—H25A	109.5
H8B—C8—H8C	109.5	C24—C25—H25B	109.5
O3—C9—H9A	109.5	H25A—C25—H25B	109.5
O3—C9—H9B	109.5	C24—C25—H25C	109.5
H9A—C9—H9B	109.5	H25A—C25—H25C	109.5
O3—C9—H9C	109.5	H25B—C25—H25C	109.5
H9A—C9—H9C	109.5	O10—C26—O11	121.3 (3)
H9B—C9—H9C	109.5	O10—C26—C11	127.0 (2)
O4—C10—C11	108.3 (2)	O11—C26—C11	111.7 (2)
O4—C10—C5	112.3 (2)	O11—C27—C28	103.8 (8)
C11—C10—C5	139.4 (2)	O11—C27—H27A	111.0
C10—C11—C12	106.3 (2)	C28—C27—H27A	111.0
C10—C11—C26	128.9 (2)	O11—C27—H27B	111.0
C12—C11—C26	124.8 (2)	C28—C27—H27B	111.0
C13—C12—C11	107.3 (2)	H27A—C27—H27B	109.0
C13—C12—C23	125.6 (2)	O11—C27'—C28'	102.9 (9)
C11—C12—C23	127.0 (2)	O11—C27'—H27C	111.2
C12—C13—O4	108.9 (2)	C28'—C27'—H27C	111.2
C12—C13—C14	136.2 (2)	O11—C27'—H27D	111.2
O4—C13—C14	114.8 (2)	C28'—C27'—H27D	111.2
C15—C14—C19	119.9 (2)	H27C—C27'—H27D	109.1
C15—C14—C13	121.0 (2)	C27'—C28'—H28D	109.5
C19—C14—C13	119.0 (2)	C27'—C28'—H28E	109.5
C16—C15—C14	120.1 (3)	H28D—C28'—H28E	109.5
C16—C15—H15	120.0	C27'—C28'—H28F	109.5
C14—C15—H15	120.0	H28D—C28'—H28F	109.5
O5—C16—C15	124.7 (3)	H28E—C28'—H28F	109.5
O5—C16—C17	115.3 (2)	C1—O1—C7	118.4 (2)
C15—C16—C17	120.0 (2)	C2—O2—C8	116.2 (3)
C18—C17—O6	119.6 (3)	C3—O3—C9	117.5 (2)
C18—C17—C16	120.0 (2)	C10—O4—C13	109.25 (18)
O6—C17—C16	120.1 (2)	C16—O5—C20	117.5 (2)
O7—C18—C17	115.7 (2)	C17—O6—C21	114.2 (2)
O7—C18—C19	124.1 (2)	C18—O7—C22	117.4 (2)
C17—C18—C19	120.1 (3)	C23—O9—C24	116.3 (2)
C18—C19—C14	119.9 (2)	C26—O11—C27	118.1 (4)
C18—C19—H19	120.0	C26—O11—C27'	113.9 (4)
O1—C1—C2—O2	4.3 (4)	O6—C17—C18—O7	5.3 (4)
C6—C1—C2—O2	−175.4 (3)	C16—C17—C18—O7	178.7 (3)
O1—C1—C2—C3	−179.7 (3)	O6—C17—C18—C19	−173.1 (3)
C6—C1—C2—C3	0.6 (4)	C16—C17—C18—C19	0.3 (4)
O2—C2—C3—O3	−4.2 (4)	O7—C18—C19—C14	−178.3 (3)
C1—C2—C3—O3	179.8 (3)	C17—C18—C19—C14	0.0 (4)
O2—C2—C3—C4	176.5 (3)	C15—C14—C19—C18	−0.3 (4)
C1—C2—C3—C4	0.5 (5)	C13—C14—C19—C18	176.7 (2)
O3—C3—C4—C5	179.2 (3)	C13—C12—C23—O8	−78.8 (4)
C2—C3—C4—C5	−1.6 (4)	C11—C12—C23—O8	96.2 (4)
C3—C4—C5—C6	1.5 (4)	C13—C12—C23—O9	97.4 (3)
C3—C4—C5—C10	−179.3 (3)	C11—C12—C23—O9	−87.6 (3)
O1—C1—C6—C5	179.7 (3)	C10—C11—C26—O10	−7.6 (5)
C2—C1—C6—C5	−0.6 (4)	C12—C11—C26—O10	171.6 (3)
C4—C5—C6—C1	−0.5 (4)	C10—C11—C26—O11	172.4 (3)
C10—C5—C6—C1	−179.6 (2)	C12—C11—C26—O11	−8.3 (4)
C4—C5—C10—O4	5.3 (3)	C2—C1—O1—C7	177.4 (3)
C6—C5—C10—O4	−175.6 (2)	C6—C1—O1—C7	−2.9 (4)
C4—C5—C10—C11	−171.6 (3)	C1—C2—O2—C8	−102.4 (4)
C6—C5—C10—C11	7.5 (5)	C3—C2—O2—C8	81.6 (4)
O4—C10—C11—C12	−1.5 (3)	C4—C3—O3—C9	−10.9 (4)
C5—C10—C11—C12	175.5 (3)	C2—C3—O3—C9	169.9 (3)
O4—C10—C11—C26	177.9 (3)	C11—C10—O4—C13	1.0 (3)
C5—C10—C11—C26	−5.2 (6)	C5—C10—O4—C13	−176.9 (2)
C10—C11—C12—C13	1.5 (3)	C12—C13—O4—C10	0.0 (3)
C26—C11—C12—C13	−177.9 (3)	C14—C13—O4—C10	−177.6 (2)
C10—C11—C12—C23	−174.3 (3)	C15—C16—O5—C20	−5.5 (5)
C26—C11—C12—C23	6.3 (4)	C17—C16—O5—C20	172.1 (3)
C11—C12—C13—O4	−0.9 (3)	C18—C17—O6—C21	−96.1 (3)
C23—C12—C13—O4	174.9 (2)	C16—C17—O6—C21	90.5 (4)
C11—C12—C13—C14	175.9 (3)	C17—C18—O7—C22	−168.8 (3)
C23—C12—C13—C14	−8.3 (5)	C19—C18—O7—C22	9.6 (4)
C12—C13—C14—C15	−4.6 (5)	O8—C23—O9—C24	0.1 (4)
O4—C13—C14—C15	172.0 (2)	C12—C23—O9—C24	−176.1 (2)
C12—C13—C14—C19	178.4 (3)	C25—C24—O9—C23	−84.7 (4)
O4—C13—C14—C19	−4.9 (4)	O10—C26—O11—C27	18.6 (6)
C19—C14—C15—C16	0.2 (4)	C11—C26—O11—C27	−161.4 (5)
C13—C14—C15—C16	−176.7 (3)	O10—C26—O11—C27'	−18.7 (6)
C14—C15—C16—O5	177.6 (3)	C11—C26—O11—C27'	161.3 (5)
C14—C15—C16—C17	0.1 (5)	C28—C27—O11—C26	−91.5 (7)
O5—C16—C17—C18	−178.0 (3)	C28—C27—O11—C27'	0.1 (7)
C15—C16—C17—C18	−0.4 (5)	C28'—C27'—O11—C26	110.9 (6)
O5—C16—C17—O6	−4.7 (4)	C28'—C27'—O11—C27	5.7 (9)
C15—C16—C17—O6	173.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O10	0.93	2.13	2.949 (3)	147
C9—H9C···O8^i	0.96	2.57	3.490 (4)	161
C22—H22A···O8^i	0.96	2.59	3.510 (4)	160
C25—H25B···O10^ii	0.96	2.60	3.540 (4)	166

Symmetry codes: (i) −x, −y+2, −z+1; (ii) x−1/2, −y+3/2, z−1/2.