Phillyrin sesquihydrate

Yin, R.-J.; Wang, X.-B.; Kong, L.-Y.

doi:10.1107/S1600536806037834

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Phillyrin sesquihydrate

R.-J. Yin, X.-B. Wang and L.-Y. Kong

The asymmetric unit of the title compound, C₂₇H₃₄O₁₁·1.5H₂O, isolated from Osmanthus armatus, contains two molecules of phillyrin and three water molecules. The phillyrin molecules have almost identical geometry; each of them contains two benzene rings, two fused tetrahydrofuran rings and a D-glucose fragment. Each of the cis-fused tetrahydrofuran rings adopts an envelope conformation with the O atom in the flap position. An extensive hydrogen-bonding system links the phillyrin and water molecules into an infinite three-dimensional framework.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037834/ya2022sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037834/ya2022Isup2.hkl Contains datablock I

CCDC reference: 625047

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.010 Å
R factor = 0.052
wR factor = 0.140
Data-to-parameter ratio = 7.1

checkCIF/PLATON results

No syntax errors found





Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H7AA   ..  H32     ..       1.90 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H9BA   ..  H29     ..       2.08 Ang.

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 .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.06
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.83 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.41 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.55 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C6A
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         24

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           25.00
           From the CIF: _reflns_number_total               5027
           Count of symmetry unique reflns         5029
           Completeness (_total/calc)             99.96%
           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 C1A    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1B    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2A    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2B    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4A    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4B    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5A    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5B    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C22A   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C22B   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23A   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23B   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C24A   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C24B   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C25A   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C25B   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C26A   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C26B   = .          R

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
  19 ALERT level G = General alerts; check

  22 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Phillyrin sesquihydrate top

Crystal data top

C₂₇H₃₄O₁₁·1.5H₂O	F(000) = 1196
M_r = 561.56	D_x = 1.386 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2183 reflections
a = 11.745 (3) Å	θ = 2.2–24.9°
b = 10.343 (2) Å	µ = 0.11 mm⁻¹
c = 22.722 (5) Å	T = 298 K
β = 102.838 (4)°	Prism, colourless
V = 2691.2 (10) Å³	0.21 × 0.16 × 0.06 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	5027 independent reflections
Radiation source: fine-focus sealed tube	2835 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→12
T_min = 0.977, T_max = 0.993	k = −11→12
14001 measured reflections	l = −21→27

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0546P)² + 1.0581P] where P = (F_o² + 2F_c²)/3
5027 reflections	(Δ/σ)_max = 0.001
712 parameters	Δρ_max = 0.46 e Å⁻³
1 restraint	Δρ_min = −0.30 e Å⁻³

Special details top

Experimental. [α]_D +45.5 (c, 0.04, MeOH), UV λ_max(MeOH) (nm): 206, 229, 278; IR γ_max(cm^-1): 3477, 1592, 1517, 1463, 1421, 1100

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	U_iso*/U_eq
O1A	0.4926 (4)	0.7960 (6)	0.53702 (19)	0.0598 (15)
O2A	0.2054 (4)	0.9489 (5)	0.45133 (19)	0.0525 (13)
O3A	0.5403 (4)	1.0809 (5)	0.7228 (2)	0.0614 (14)
O4A	0.4112 (4)	0.9886 (6)	0.7887 (2)	0.0695 (16)
O5A	0.3352 (4)	1.0392 (5)	0.22149 (19)	0.0525 (13)
O6A	0.1521 (3)	0.9081 (4)	0.16889 (18)	0.0404 (11)
O7A	0.0069 (4)	1.0916 (5)	0.0952 (2)	0.0613 (14)
H7AA	0.0743	1.1181	0.1017	0.092*
O8A	−0.1458 (4)	0.9858 (5)	−0.00729 (19)	0.0605 (15)
H8AA	−0.2148	1.0073	−0.0148	0.091*
O9A	−0.2522 (4)	0.7469 (5)	0.0209 (2)	0.0744 (17)
H9AA	−0.2777	0.7760	−0.0130	0.112*
O10A	0.0294 (3)	0.7459 (4)	0.12693 (17)	0.0392 (11)
O11A	−0.0900 (5)	0.4832 (6)	0.1372 (2)	0.0769 (17)
H11A	−0.0272	0.4864	0.1616	0.115*
O1B	0.0090 (4)	0.2976 (6)	0.46792 (18)	0.0591 (15)
O2B	0.2899 (4)	0.4525 (5)	0.55830 (18)	0.0563 (14)
O3B	−0.0377 (4)	0.5604 (5)	0.2757 (2)	0.0599 (14)
O4B	0.1230 (4)	0.4898 (6)	0.2229 (2)	0.0644 (16)
O5B	0.1312 (4)	0.5528 (5)	0.78016 (18)	0.0506 (13)
O6B	0.3131 (3)	0.4294 (4)	0.83830 (16)	0.0382 (11)
O7B	0.4205 (4)	0.6415 (5)	0.9121 (2)	0.0505 (12)
H7BA	0.3513	0.6536	0.9116	0.076*
O8B	0.5849 (4)	0.5528 (5)	1.01860 (17)	0.0506 (13)
H8BA	0.6323	0.6123	1.0242	0.076*
O9B	0.7469 (4)	0.3678 (5)	0.98447 (19)	0.0549 (14)
H9BA	0.7643	0.3293	1.0168	0.082*
O10B	0.4720 (3)	0.3032 (4)	0.87769 (16)	0.0371 (11)
O11B	0.6200 (4)	0.0823 (5)	0.9419 (2)	0.0583 (14)
H11B	0.5527	0.0910	0.9459	0.087*
O12	0.8074 (4)	0.2377 (5)	0.0942 (2)	0.0659 (15)
H28	0.8296	0.3038	0.1168	0.099*
H29	0.8683	0.2133	0.0820	0.099*
O13	0.6086 (4)	0.8172 (5)	0.9091 (2)	0.0679 (15)
H30	0.5479	0.7823	0.9178	0.102*
H31	0.5815	0.8850	0.8889	0.102*
O14	0.2229 (7)	0.1654 (9)	0.1158 (3)	0.145 (3)
H32	0.2337	0.1068	0.1433	0.218*
H33	0.2902	0.2010	0.1188	0.218*
C1A	0.4005 (6)	0.7514 (8)	0.5638 (3)	0.0514 (19)
H1AA	0.4084	0.6578	0.5701	0.062*
C2A	0.2898 (6)	0.7785 (7)	0.5148 (3)	0.0429 (18)
H2AA	0.2289	0.7144	0.5159	0.052*
C3A	0.2421 (6)	0.9151 (8)	0.5136 (3)	0.054 (2)
H3AA	0.1767	0.9184	0.5332	0.065*
H3AB	0.3021	0.9741	0.5343	0.065*
C4A	0.2962 (6)	0.9022 (7)	0.4240 (3)	0.0465 (18)
H4AA	0.3631	0.9611	0.4344	0.056*
C5A	0.3312 (5)	0.7702 (7)	0.4551 (3)	0.0446 (18)
H5AA	0.2937	0.6982	0.4301	0.053*
C6A	0.4635 (6)	0.7488 (10)	0.4761 (3)	0.068 (2)
H6AA	0.4826	0.6578	0.4747	0.082*
H6AB	0.5054	0.7965	0.4509	0.082*
C7A	0.4044 (5)	0.8159 (7)	0.6237 (3)	0.0402 (17)
C8A	0.4744 (5)	0.9217 (7)	0.6441 (3)	0.0434 (17)
H8AB	0.5220	0.9562	0.6203	0.052*
C9A	0.4739 (5)	0.9759 (7)	0.6991 (3)	0.0420 (17)
C10A	0.4029 (6)	0.9272 (8)	0.7355 (3)	0.052 (2)
C11A	0.3341 (6)	0.8229 (8)	0.7155 (3)	0.054 (2)
H11C	0.2868	0.7883	0.7394	0.065*
C12A	0.3339 (6)	0.7673 (8)	0.6593 (3)	0.053 (2)
H12A	0.2857	0.6970	0.6459	0.063*
C13A	0.6091 (7)	1.1401 (8)	0.6871 (3)	0.071 (2)
H13A	0.6507	1.2116	0.7088	0.107*
H13B	0.5598	1.1706	0.6503	0.107*
H13C	0.6639	1.0784	0.6780	0.107*
C14A	0.3328 (7)	0.9505 (12)	0.8258 (3)	0.100 (4)
H14A	0.3479	1.0013	0.8620	0.150*
H14B	0.3442	0.8607	0.8360	0.150*
H14C	0.2537	0.9641	0.8041	0.150*
C15A	0.2549 (6)	0.8993 (7)	0.3566 (3)	0.0455 (18)
C16A	0.3156 (6)	0.9712 (7)	0.3212 (3)	0.0454 (18)
H16A	0.3802	1.0196	0.3400	0.054*
C17A	0.2814 (6)	0.9716 (7)	0.2594 (3)	0.0406 (17)
C18A	0.1830 (5)	0.9004 (7)	0.2308 (3)	0.0366 (16)
C19A	0.1242 (5)	0.8282 (7)	0.2661 (3)	0.0405 (17)
H19A	0.0600	0.7789	0.2476	0.049*
C20A	0.1598 (5)	0.8284 (7)	0.3284 (3)	0.0427 (17)
H20A	0.1188	0.7800	0.3513	0.051*
C21A	0.4348 (6)	1.1177 (7)	0.2483 (3)	0.057 (2)
H21A	0.4641	1.1598	0.2170	0.086*
H21B	0.4947	1.0638	0.2717	0.086*
H21C	0.4118	1.1816	0.2740	0.086*
C22A	0.0346 (5)	0.8819 (7)	0.1399 (3)	0.0376 (17)
H22A	−0.0185	0.9048	0.1660	0.045*
C23A	0.0049 (5)	0.9557 (6)	0.0814 (3)	0.0368 (16)
H23A	0.0603	0.9355	0.0562	0.044*
C24A	−0.1182 (5)	0.9214 (7)	0.0492 (3)	0.0416 (17)
H24A	−0.1724	0.9497	0.0738	0.050*
C25A	−0.1284 (6)	0.7796 (7)	0.0406 (3)	0.0484 (19)
H25A	−0.0853	0.7513	0.0106	0.058*
C26A	−0.0882 (6)	0.7053 (7)	0.0990 (3)	0.0418 (18)
H26A	−0.1408	0.7217	0.1262	0.050*
C27A	−0.0840 (6)	0.5590 (7)	0.0856 (3)	0.062 (2)
H27A	−0.1489	0.5367	0.0526	0.074*
H27B	−0.0122	0.5394	0.0731	0.074*
C1B	0.1045 (6)	0.2531 (8)	0.4445 (3)	0.0450 (18)
H1BA	0.0974	0.1594	0.4385	0.054*
C2B	0.2115 (6)	0.2813 (7)	0.4954 (3)	0.0385 (16)
H2BA	0.2728	0.2167	0.4962	0.046*
C3B	0.2596 (6)	0.4166 (7)	0.4958 (3)	0.0492 (19)
H3BA	0.3278	0.4180	0.4784	0.059*
H3BB	0.2013	0.4749	0.4732	0.059*
C4B	0.1945 (6)	0.4075 (7)	0.5823 (3)	0.0478 (18)
H4BA	0.1281	0.4658	0.5687	0.057*
C5B	0.1625 (5)	0.2731 (7)	0.5528 (3)	0.0408 (17)
H5BA	0.1984	0.2025	0.5793	0.049*
C6B	0.0332 (6)	0.2519 (9)	0.5291 (3)	0.062 (2)
H6BA	0.0138	0.1610	0.5305	0.075*
H6BB	−0.0115	0.3003	0.5528	0.075*
C7B	0.1085 (5)	0.3166 (7)	0.3848 (3)	0.0395 (17)
C8B	0.0294 (5)	0.4118 (7)	0.3585 (3)	0.0398 (17)
H8BB	−0.0288	0.4380	0.3778	0.048*
C9B	0.0364 (6)	0.4668 (6)	0.3052 (3)	0.0395 (17)
C10B	0.1237 (6)	0.4285 (7)	0.2762 (3)	0.0412 (17)
C11B	0.2010 (6)	0.3349 (8)	0.3019 (3)	0.057 (2)
H11D	0.2589	0.3083	0.2824	0.069*
C12B	0.1943 (6)	0.2794 (8)	0.3561 (3)	0.057 (2)
H12B	0.2482	0.2166	0.3734	0.069*
C13B	−0.1207 (6)	0.6144 (8)	0.3046 (4)	0.064 (2)
H13D	−0.1659	0.6780	0.2787	0.097*
H13E	−0.0813	0.6546	0.3416	0.097*
H13F	−0.1713	0.5476	0.3132	0.097*
C14B	0.2011 (7)	0.4436 (12)	0.1876 (3)	0.099 (4)
H14D	0.1921	0.4946	0.1515	0.149*
H14E	0.1836	0.3548	0.1769	0.149*
H14F	0.2800	0.4504	0.2105	0.149*
C15B	0.2271 (5)	0.4100 (7)	0.6504 (3)	0.0411 (17)
C16B	0.1600 (6)	0.4789 (7)	0.6823 (3)	0.0426 (18)
H16B	0.0939	0.5224	0.6615	0.051*
C17B	0.1894 (5)	0.4842 (7)	0.7445 (3)	0.0352 (16)
C18B	0.2884 (5)	0.4193 (7)	0.7757 (3)	0.0374 (16)
C19B	0.3536 (5)	0.3482 (7)	0.7444 (3)	0.0430 (18)
H19B	0.4181	0.3020	0.7650	0.052*
C20B	0.3233 (6)	0.3450 (7)	0.6818 (3)	0.0443 (18)
H20B	0.3691	0.2981	0.6608	0.053*
C21B	0.0380 (6)	0.6358 (8)	0.7516 (3)	0.058 (2)
H21D	0.0054	0.6776	0.7818	0.088*
H21E	−0.0213	0.5857	0.7255	0.088*
H21F	0.0674	0.7000	0.7283	0.088*
C22B	0.4330 (5)	0.4333 (7)	0.8660 (3)	0.0352 (16)
H22B	0.4765	0.4752	0.8391	0.042*
C23B	0.4484 (5)	0.5083 (6)	0.9244 (3)	0.0348 (16)
H23B	0.3976	0.4722	0.9491	0.042*
C24B	0.5748 (5)	0.5013 (6)	0.9587 (3)	0.0363 (16)
H24B	0.6218	0.5550	0.9376	0.044*
C25B	0.6228 (5)	0.3654 (7)	0.9628 (3)	0.0371 (16)
H25B	0.5870	0.3137	0.9899	0.044*
C26B	0.5975 (5)	0.3036 (7)	0.8997 (3)	0.0384 (16)
H26B	0.6321	0.3580	0.8729	0.046*
C27B	0.6399 (7)	0.1669 (7)	0.8962 (3)	0.053 (2)
H27C	0.6021	0.1311	0.8573	0.063*
H27D	0.7232	0.1693	0.8980	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.045 (3)	0.093 (5)	0.038 (3)	−0.006 (3)	0.003 (2)	−0.009 (3)
O2A	0.066 (3)	0.056 (3)	0.034 (3)	0.016 (3)	0.008 (2)	−0.006 (2)
O3A	0.071 (3)	0.062 (4)	0.055 (3)	−0.020 (3)	0.022 (3)	−0.014 (3)
O4A	0.070 (3)	0.090 (5)	0.054 (3)	−0.007 (3)	0.024 (3)	−0.011 (3)
O5A	0.053 (3)	0.056 (3)	0.047 (3)	−0.023 (3)	0.008 (2)	−0.003 (2)
O6A	0.035 (2)	0.048 (3)	0.035 (2)	−0.005 (2)	0.002 (2)	−0.002 (2)
O7A	0.055 (3)	0.043 (3)	0.078 (4)	−0.006 (3)	0.000 (3)	0.000 (3)
O8A	0.047 (3)	0.081 (4)	0.047 (3)	0.002 (3)	−0.004 (2)	0.028 (3)
O9A	0.060 (3)	0.076 (4)	0.068 (4)	−0.025 (3)	−0.026 (3)	0.014 (3)
O10A	0.038 (3)	0.038 (3)	0.037 (3)	−0.001 (2)	0.000 (2)	−0.006 (2)
O11A	0.080 (4)	0.070 (4)	0.076 (4)	−0.006 (3)	0.006 (3)	0.011 (3)
O1B	0.044 (3)	0.096 (5)	0.033 (3)	−0.004 (3)	−0.001 (2)	0.015 (3)
O2B	0.071 (3)	0.063 (4)	0.033 (3)	−0.029 (3)	0.009 (2)	0.001 (2)
O3B	0.066 (3)	0.067 (4)	0.049 (3)	0.024 (3)	0.018 (3)	0.016 (3)
O4B	0.061 (3)	0.087 (4)	0.049 (3)	0.011 (3)	0.020 (3)	0.020 (3)
O5B	0.051 (3)	0.066 (4)	0.035 (3)	0.019 (3)	0.010 (2)	0.013 (2)
O6B	0.032 (2)	0.054 (3)	0.025 (2)	0.000 (2)	−0.0007 (18)	−0.001 (2)
O7B	0.043 (3)	0.041 (3)	0.065 (3)	0.005 (2)	0.005 (2)	−0.001 (2)
O8B	0.056 (3)	0.052 (3)	0.039 (3)	−0.010 (3)	0.001 (2)	−0.015 (2)
O9B	0.041 (3)	0.064 (4)	0.051 (3)	0.001 (2)	−0.008 (2)	0.005 (2)
O10B	0.038 (2)	0.037 (3)	0.033 (2)	0.000 (2)	−0.0012 (19)	0.000 (2)
O11B	0.063 (3)	0.052 (3)	0.061 (3)	0.007 (3)	0.017 (3)	0.017 (3)
O12	0.063 (3)	0.063 (4)	0.065 (3)	0.009 (3)	−0.001 (3)	0.003 (3)
O13	0.055 (3)	0.057 (4)	0.087 (4)	0.009 (3)	0.006 (3)	0.011 (3)
O14	0.120 (6)	0.153 (8)	0.160 (7)	−0.026 (6)	0.026 (5)	0.052 (6)
C1A	0.044 (4)	0.060 (5)	0.042 (4)	0.000 (4)	−0.009 (3)	−0.001 (4)
C2A	0.044 (4)	0.046 (5)	0.033 (4)	−0.008 (4)	−0.003 (3)	−0.005 (3)
C3A	0.058 (5)	0.063 (6)	0.041 (4)	0.008 (4)	0.007 (4)	−0.010 (4)
C4A	0.053 (4)	0.049 (5)	0.035 (4)	−0.003 (4)	0.004 (3)	−0.014 (4)
C5A	0.044 (4)	0.046 (5)	0.037 (4)	0.005 (4)	−0.004 (3)	−0.011 (3)
C6A	0.048 (5)	0.109 (7)	0.042 (5)	0.012 (5)	−0.001 (4)	−0.007 (5)
C7A	0.033 (4)	0.053 (5)	0.031 (4)	−0.004 (4)	−0.001 (3)	0.002 (3)
C8A	0.043 (4)	0.050 (5)	0.035 (4)	−0.013 (4)	0.003 (3)	0.004 (3)
C9A	0.036 (4)	0.047 (5)	0.040 (4)	−0.008 (4)	0.003 (3)	0.000 (4)
C10A	0.046 (4)	0.070 (6)	0.037 (4)	−0.003 (4)	0.005 (3)	−0.001 (4)
C11A	0.045 (4)	0.073 (6)	0.050 (5)	−0.007 (4)	0.021 (4)	0.008 (4)
C12A	0.043 (4)	0.055 (5)	0.055 (5)	−0.021 (4)	0.000 (4)	0.000 (4)
C13A	0.079 (6)	0.064 (6)	0.075 (6)	−0.028 (5)	0.024 (5)	−0.004 (5)
C14A	0.082 (6)	0.182 (12)	0.046 (5)	−0.002 (7)	0.035 (5)	0.011 (6)
C15A	0.049 (4)	0.044 (5)	0.040 (4)	0.000 (4)	0.002 (3)	0.001 (4)
C16A	0.043 (4)	0.051 (5)	0.039 (4)	−0.001 (4)	0.002 (3)	−0.014 (4)
C17A	0.044 (4)	0.042 (4)	0.034 (4)	−0.005 (3)	0.005 (3)	−0.002 (3)
C18A	0.037 (4)	0.039 (4)	0.029 (4)	−0.001 (3)	−0.002 (3)	−0.002 (3)
C19A	0.034 (4)	0.049 (5)	0.035 (4)	−0.010 (3)	0.001 (3)	−0.001 (3)
C20A	0.041 (4)	0.050 (5)	0.037 (4)	−0.004 (4)	0.006 (3)	0.001 (3)
C21A	0.044 (4)	0.055 (5)	0.072 (5)	−0.020 (4)	0.011 (4)	−0.019 (4)
C22A	0.031 (4)	0.043 (5)	0.036 (4)	−0.003 (3)	0.002 (3)	−0.007 (3)
C23A	0.037 (4)	0.032 (4)	0.041 (4)	−0.002 (3)	0.008 (3)	0.002 (3)
C24A	0.035 (4)	0.049 (5)	0.038 (4)	0.000 (4)	0.002 (3)	0.008 (3)
C25A	0.047 (4)	0.051 (5)	0.040 (4)	−0.014 (4)	−0.008 (3)	0.003 (3)
C26A	0.042 (4)	0.049 (5)	0.030 (4)	−0.007 (4)	−0.001 (3)	−0.001 (3)
C27A	0.054 (5)	0.047 (5)	0.071 (5)	−0.019 (4)	−0.014 (4)	0.030 (4)
C1B	0.043 (4)	0.057 (5)	0.031 (4)	−0.002 (4)	−0.001 (3)	0.002 (3)
C2B	0.043 (4)	0.041 (5)	0.030 (4)	0.002 (3)	0.006 (3)	0.004 (3)
C3B	0.067 (5)	0.050 (5)	0.030 (4)	−0.010 (4)	0.008 (3)	−0.002 (3)
C4B	0.053 (4)	0.052 (5)	0.036 (4)	0.000 (4)	0.004 (3)	−0.001 (4)
C5B	0.048 (4)	0.043 (5)	0.028 (3)	−0.005 (3)	0.002 (3)	0.012 (3)
C6B	0.052 (5)	0.090 (6)	0.038 (4)	−0.021 (5)	−0.004 (3)	0.015 (4)
C7B	0.041 (4)	0.048 (4)	0.026 (3)	0.004 (4)	0.000 (3)	0.001 (3)
C8B	0.038 (4)	0.051 (5)	0.031 (4)	0.008 (4)	0.007 (3)	−0.004 (3)
C9B	0.049 (4)	0.033 (4)	0.031 (4)	0.008 (3)	−0.001 (3)	0.006 (3)
C10B	0.044 (4)	0.050 (5)	0.029 (4)	0.003 (4)	0.006 (3)	0.000 (3)
C11B	0.047 (4)	0.083 (6)	0.043 (4)	0.017 (4)	0.013 (4)	0.000 (4)
C12B	0.051 (5)	0.073 (6)	0.046 (5)	0.025 (4)	0.006 (4)	0.008 (4)
C13B	0.062 (5)	0.051 (6)	0.083 (6)	0.026 (4)	0.021 (4)	0.005 (4)
C14B	0.066 (5)	0.185 (12)	0.058 (5)	0.013 (7)	0.037 (5)	0.020 (7)
C15B	0.041 (4)	0.051 (5)	0.030 (4)	−0.003 (4)	0.005 (3)	0.006 (3)
C16B	0.041 (4)	0.047 (5)	0.035 (4)	−0.001 (4)	−0.002 (3)	0.002 (3)
C17B	0.028 (3)	0.040 (4)	0.038 (4)	0.004 (3)	0.010 (3)	0.000 (3)
C18B	0.034 (4)	0.047 (5)	0.030 (4)	0.001 (3)	0.006 (3)	0.003 (3)
C19B	0.036 (4)	0.056 (5)	0.032 (4)	0.003 (4)	−0.002 (3)	0.000 (3)
C20B	0.044 (4)	0.052 (5)	0.037 (4)	0.010 (4)	0.008 (3)	−0.005 (3)
C21B	0.051 (4)	0.067 (6)	0.056 (5)	0.017 (4)	0.007 (4)	0.011 (4)
C22B	0.034 (4)	0.038 (4)	0.029 (3)	0.005 (3)	−0.002 (3)	0.005 (3)
C23B	0.041 (4)	0.030 (4)	0.030 (3)	0.004 (3)	0.001 (3)	0.001 (3)
C24B	0.039 (4)	0.035 (4)	0.032 (4)	−0.002 (3)	0.002 (3)	−0.002 (3)
C25B	0.034 (4)	0.042 (4)	0.029 (4)	0.000 (3)	−0.005 (3)	0.005 (3)
C26B	0.042 (4)	0.039 (4)	0.032 (3)	0.005 (3)	0.004 (3)	0.003 (3)
C27B	0.060 (5)	0.051 (5)	0.047 (4)	0.015 (4)	0.010 (4)	0.007 (4)

Geometric parameters (Å, º) top

O1A—C1A	1.431 (8)	C14A—H14C	0.9600
O1A—C6A	1.435 (7)	C15A—C20A	1.371 (8)
O2A—C3A	1.429 (8)	C15A—C16A	1.400 (9)
O2A—C4A	1.431 (8)	C16A—C17A	1.372 (8)
O3A—C9A	1.375 (8)	C16A—H16A	0.9300
O3A—C13A	1.405 (8)	C17A—C18A	1.402 (8)
O4A—C10A	1.350 (8)	C18A—C19A	1.387 (8)
O4A—C14A	1.434 (8)	C19A—C20A	1.384 (8)
O5A—C17A	1.369 (7)	C19A—H19A	0.9300
O5A—C21A	1.442 (7)	C20A—H20A	0.9300
O6A—C18A	1.375 (7)	C21A—H21A	0.9600
O6A—C22A	1.417 (7)	C21A—H21B	0.9600
O7A—C23A	1.440 (8)	C21A—H21C	0.9600
O7A—H7AA	0.8200	C22A—C23A	1.504 (8)
O8A—C24A	1.419 (7)	C22A—H22A	0.9800
O8A—H8AA	0.8200	C23A—C24A	1.511 (8)
O9A—C25A	1.463 (8)	C23A—H23A	0.9800
O9A—H9AA	0.8200	C24A—C25A	1.481 (10)
O10A—C22A	1.436 (8)	C24A—H24A	0.9800
O10A—C26A	1.449 (7)	C25A—C26A	1.515 (8)
O11A—C27A	1.426 (8)	C25A—H25A	0.9800
O11A—H11A	0.8200	C26A—C27A	1.546 (10)
O1B—C1B	1.420 (8)	C26A—H26A	0.9800
O1B—C6B	1.436 (7)	C27A—H27A	0.9700
O2B—C4B	1.428 (8)	C27A—H27B	0.9700
O2B—C3B	1.434 (7)	C1B—C7B	1.518 (9)
O3B—C9B	1.372 (7)	C1B—C2B	1.535 (8)
O3B—C13B	1.406 (8)	C1B—H1BA	0.9800
O4B—C10B	1.367 (8)	C2B—C3B	1.509 (9)
O4B—C14B	1.428 (9)	C2B—C5B	1.539 (8)
O5B—C17B	1.369 (7)	C2B—H2BA	0.9800
O5B—C21B	1.428 (8)	C3B—H3BA	0.9700
O6B—C18B	1.391 (7)	C3B—H3BB	0.9700
O6B—C22B	1.409 (6)	C4B—C15B	1.511 (8)
O7B—C23B	1.429 (7)	C4B—C5B	1.553 (9)
O7B—H7BA	0.8200	C4B—H4BA	0.9800
O8B—C24B	1.442 (7)	C5B—C6B	1.510 (9)
O8B—H8BA	0.8200	C5B—H5BA	0.9800
O9B—C25B	1.431 (7)	C6B—H6BA	0.9700
O9B—H9BA	0.8200	C6B—H6BB	0.9700
O10B—C22B	1.428 (8)	C7B—C12B	1.371 (9)
O10B—C26B	1.447 (7)	C7B—C8B	1.394 (9)
O11B—C27B	1.416 (8)	C8B—C9B	1.358 (8)
O11B—H11B	0.8200	C8B—H8BB	0.9300
O12—H28	0.8600	C9B—C10B	1.393 (9)
O12—H29	0.8599	C10B—C11B	1.366 (9)
O13—H30	0.8601	C11B—C12B	1.378 (9)
O13—H31	0.8600	C11B—H11D	0.9300
O14—H32	0.8600	C12B—H12B	0.9300
O14—H33	0.8601	C13B—H13D	0.9600
C1A—C7A	1.507 (9)	C13B—H13E	0.9600
C1A—C2A	1.539 (8)	C13B—H13F	0.9600
C1A—H1AA	0.9800	C14B—H14D	0.9600
C2A—C3A	1.518 (10)	C14B—H14E	0.9600
C2A—C5A	1.540 (9)	C14B—H14F	0.9600
C2A—H2AA	0.9800	C15B—C20B	1.371 (8)
C3A—H3AA	0.9700	C15B—C16B	1.382 (9)
C3A—H3AB	0.9700	C16B—C17B	1.378 (8)
C4A—C15A	1.501 (8)	C16B—H16B	0.9300
C4A—C5A	1.551 (10)	C17B—C18B	1.393 (8)
C4A—H4AA	0.9800	C18B—C19B	1.369 (8)
C5A—C6A	1.536 (9)	C19B—C20B	1.386 (8)
C5A—H5AA	0.9800	C19B—H19B	0.9300
C6A—H6AA	0.9700	C20B—H20B	0.9300
C6A—H6AB	0.9700	C21B—H21D	0.9600
C7A—C12A	1.375 (9)	C21B—H21E	0.9600
C7A—C8A	1.385 (9)	C21B—H21F	0.9600
C8A—C9A	1.370 (9)	C22B—C23B	1.513 (8)
C8A—H8AB	0.9300	C22B—H22B	0.9800
C9A—C10A	1.393 (9)	C23B—C24B	1.518 (8)
C10A—C11A	1.365 (10)	C23B—H23B	0.9800
C11A—C12A	1.400 (10)	C24B—C25B	1.509 (9)
C11A—H11C	0.9300	C24B—H24B	0.9800
C12A—H12A	0.9300	C25B—C26B	1.537 (8)
C13A—H13A	0.9600	C25B—H25B	0.9800
C13A—H13B	0.9600	C26B—C27B	1.507 (9)
C13A—H13C	0.9600	C26B—H26B	0.9800
C14A—H14A	0.9600	C27B—H27C	0.9700
C14A—H14B	0.9600	C27B—H27D	0.9700

C1A—O1A—C6A	105.1 (5)	O10A—C26A—C25A	108.5 (5)
C3A—O2A—C4A	104.9 (5)	O10A—C26A—C27A	107.5 (5)
C9A—O3A—C13A	117.9 (6)	C25A—C26A—C27A	110.0 (6)
C10A—O4A—C14A	118.0 (7)	O10A—C26A—H26A	110.3
C17A—O5A—C21A	117.8 (5)	C25A—C26A—H26A	110.3
C18A—O6A—C22A	118.2 (5)	C27A—C26A—H26A	110.3
C23A—O7A—H7AA	109.5	O11A—C27A—C26A	111.5 (7)
C24A—O8A—H8AA	109.5	O11A—C27A—H27A	109.3
C25A—O9A—H9AA	109.5	C26A—C27A—H27A	109.3
C22A—O10A—C26A	111.5 (5)	O11A—C27A—H27B	109.3
C27A—O11A—H11A	109.5	C26A—C27A—H27B	109.3
C1B—O1B—C6B	104.7 (5)	H27A—C27A—H27B	108.0
C4B—O2B—C3B	104.5 (5)	O1B—C1B—C7B	112.3 (6)
C9B—O3B—C13B	118.8 (5)	O1B—C1B—C2B	103.8 (5)
C10B—O4B—C14B	117.7 (6)	C7B—C1B—C2B	114.2 (6)
C17B—O5B—C21B	118.4 (5)	O1B—C1B—H1BA	108.8
C18B—O6B—C22B	114.8 (4)	C7B—C1B—H1BA	108.8
C23B—O7B—H7BA	109.5	C2B—C1B—H1BA	108.8
C24B—O8B—H8BA	109.5	C3B—C2B—C1B	115.0 (6)
C25B—O9B—H9BA	109.5	C3B—C2B—C5B	104.8 (5)
C22B—O10B—C26B	108.7 (5)	C1B—C2B—C5B	103.4 (5)
C27B—O11B—H11B	109.5	C3B—C2B—H2BA	111.1
H28—O12—H29	105.2	C1B—C2B—H2BA	111.1
H30—O13—H31	103.7	C5B—C2B—H2BA	111.1
H32—O14—H33	105.0	O2B—C3B—C2B	104.9 (5)
O1A—C1A—C7A	111.6 (6)	O2B—C3B—H3BA	110.8
O1A—C1A—C2A	103.3 (5)	C2B—C3B—H3BA	110.8
C7A—C1A—C2A	115.2 (6)	O2B—C3B—H3BB	110.8
O1A—C1A—H1AA	108.8	C2B—C3B—H3BB	110.8
C7A—C1A—H1AA	108.8	H3BA—C3B—H3BB	108.9
C2A—C1A—H1AA	108.8	O2B—C4B—C15B	110.1 (5)
C3A—C2A—C1A	115.5 (6)	O2B—C4B—C5B	105.2 (5)
C3A—C2A—C5A	103.0 (5)	C15B—C4B—C5B	116.1 (6)
C1A—C2A—C5A	104.2 (5)	O2B—C4B—H4BA	108.4
C3A—C2A—H2AA	111.2	C15B—C4B—H4BA	108.4
C1A—C2A—H2AA	111.2	C5B—C4B—H4BA	108.4
C5A—C2A—H2AA	111.2	C6B—C5B—C2B	104.0 (5)
O2A—C3A—C2A	105.9 (5)	C6B—C5B—C4B	114.3 (6)
O2A—C3A—H3AA	110.6	C2B—C5B—C4B	102.5 (5)
C2A—C3A—H3AA	110.6	C6B—C5B—H5BA	111.8
O2A—C3A—H3AB	110.6	C2B—C5B—H5BA	111.8
C2A—C3A—H3AB	110.6	C4B—C5B—H5BA	111.8
H3AA—C3A—H3AB	108.7	O1B—C6B—C5B	105.3 (5)
O2A—C4A—C15A	110.3 (5)	O1B—C6B—H6BA	110.7
O2A—C4A—C5A	104.3 (5)	C5B—C6B—H6BA	110.7
C15A—C4A—C5A	116.2 (5)	O1B—C6B—H6BB	110.7
O2A—C4A—H4AA	108.6	C5B—C6B—H6BB	110.7
C15A—C4A—H4AA	108.6	H6BA—C6B—H6BB	108.8
C5A—C4A—H4AA	108.6	C12B—C7B—C8B	119.1 (6)
C6A—C5A—C2A	103.3 (5)	C12B—C7B—C1B	118.4 (6)
C6A—C5A—C4A	114.6 (7)	C8B—C7B—C1B	122.5 (6)
C2A—C5A—C4A	104.4 (5)	C9B—C8B—C7B	120.7 (6)
C6A—C5A—H5AA	111.4	C9B—C8B—H8BB	119.6
C2A—C5A—H5AA	111.4	C7B—C8B—H8BB	119.6
C4A—C5A—H5AA	111.4	C8B—C9B—O3B	125.0 (6)
O1A—C6A—C5A	105.0 (6)	C8B—C9B—C10B	119.9 (6)
O1A—C6A—H6AA	110.8	O3B—C9B—C10B	115.1 (6)
C5A—C6A—H6AA	110.8	C11B—C10B—O4B	125.4 (6)
O1A—C6A—H6AB	110.8	C11B—C10B—C9B	119.3 (6)
C5A—C6A—H6AB	110.8	O4B—C10B—C9B	115.2 (6)
H6AA—C6A—H6AB	108.8	C10B—C11B—C12B	120.8 (7)
C12A—C7A—C8A	118.9 (6)	C10B—C11B—H11D	119.6
C12A—C7A—C1A	117.9 (7)	C12B—C11B—H11D	119.6
C8A—C7A—C1A	123.2 (6)	C7B—C12B—C11B	120.1 (7)
C9A—C8A—C7A	120.3 (6)	C7B—C12B—H12B	119.9
C9A—C8A—H8AB	119.8	C11B—C12B—H12B	119.9
C7A—C8A—H8AB	119.8	O3B—C13B—H13D	109.5
C8A—C9A—O3A	124.3 (6)	O3B—C13B—H13E	109.5
C8A—C9A—C10A	121.3 (7)	H13D—C13B—H13E	109.5
O3A—C9A—C10A	114.5 (6)	O3B—C13B—H13F	109.5
O4A—C10A—C11A	126.1 (7)	H13D—C13B—H13F	109.5
O4A—C10A—C9A	115.4 (7)	H13E—C13B—H13F	109.5
C11A—C10A—C9A	118.4 (7)	O4B—C14B—H14D	109.5
C10A—C11A—C12A	120.6 (7)	O4B—C14B—H14E	109.5
C10A—C11A—H11C	119.7	H14D—C14B—H14E	109.5
C12A—C11A—H11C	119.7	O4B—C14B—H14F	109.5
C7A—C12A—C11A	120.5 (7)	H14D—C14B—H14F	109.5
C7A—C12A—H12A	119.8	H14E—C14B—H14F	109.5
C11A—C12A—H12A	119.8	C20B—C15B—C16B	118.7 (6)
O3A—C13A—H13A	109.5	C20B—C15B—C4B	121.1 (6)
O3A—C13A—H13B	109.5	C16B—C15B—C4B	120.2 (6)
H13A—C13A—H13B	109.5	C17B—C16B—C15B	121.0 (6)
O3A—C13A—H13C	109.5	C17B—C16B—H16B	119.5
H13A—C13A—H13C	109.5	C15B—C16B—H16B	119.5
H13B—C13A—H13C	109.5	O5B—C17B—C16B	125.7 (6)
O4A—C14A—H14A	109.5	O5B—C17B—C18B	114.7 (5)
O4A—C14A—H14B	109.5	C16B—C17B—C18B	119.6 (6)
H14A—C14A—H14B	109.5	C19B—C18B—O6B	123.9 (6)
O4A—C14A—H14C	109.5	C19B—C18B—C17B	119.6 (6)
H14A—C14A—H14C	109.5	O6B—C18B—C17B	116.4 (6)
H14B—C14A—H14C	109.5	C18B—C19B—C20B	120.0 (6)
C20A—C15A—C16A	118.8 (6)	C18B—C19B—H19B	120.0
C20A—C15A—C4A	122.2 (6)	C20B—C19B—H19B	120.0
C16A—C15A—C4A	119.0 (6)	C15B—C20B—C19B	121.0 (6)
C17A—C16A—C15A	121.2 (6)	C15B—C20B—H20B	119.5
C17A—C16A—H16A	119.4	C19B—C20B—H20B	119.5
C15A—C16A—H16A	119.4	O5B—C21B—H21D	109.5
O5A—C17A—C16A	125.1 (6)	O5B—C21B—H21E	109.5
O5A—C17A—C18A	115.1 (5)	H21D—C21B—H21E	109.5
C16A—C17A—C18A	119.8 (6)	O5B—C21B—H21F	109.5
O6A—C18A—C19A	124.7 (6)	H21D—C21B—H21F	109.5
O6A—C18A—C17A	116.6 (6)	H21E—C21B—H21F	109.5
C19A—C18A—C17A	118.7 (6)	O6B—C22B—O10B	107.7 (5)
C20A—C19A—C18A	120.9 (6)	O6B—C22B—C23B	108.6 (5)
C20A—C19A—H19A	119.5	O10B—C22B—C23B	110.4 (5)
C18A—C19A—H19A	119.5	O6B—C22B—H22B	110.0
C15A—C20A—C19A	120.6 (6)	O10B—C22B—H22B	110.0
C15A—C20A—H20A	119.7	C23B—C22B—H22B	110.0
C19A—C20A—H20A	119.7	O7B—C23B—C22B	110.2 (5)
O5A—C21A—H21A	109.5	O7B—C23B—C24B	107.6 (5)
O5A—C21A—H21B	109.5	C22B—C23B—C24B	109.8 (5)
H21A—C21A—H21B	109.5	O7B—C23B—H23B	109.7
O5A—C21A—H21C	109.5	C22B—C23B—H23B	109.7
H21A—C21A—H21C	109.5	C24B—C23B—H23B	109.7
H21B—C21A—H21C	109.5	O8B—C24B—C25B	109.6 (5)
O6A—C22A—O10A	106.0 (5)	O8B—C24B—C23B	109.4 (5)
O6A—C22A—C23A	108.9 (5)	C25B—C24B—C23B	112.7 (5)
O10A—C22A—C23A	108.9 (5)	O8B—C24B—H24B	108.3
O6A—C22A—H22A	111.0	C25B—C24B—H24B	108.3
O10A—C22A—H22A	111.0	C23B—C24B—H24B	108.3
C23A—C22A—H22A	111.0	O9B—C25B—C24B	110.1 (5)
O7A—C23A—C22A	108.3 (5)	O9B—C25B—C26B	107.5 (5)
O7A—C23A—C24A	107.6 (5)	C24B—C25B—C26B	109.8 (5)
C22A—C23A—C24A	108.5 (5)	O9B—C25B—H25B	109.8
O7A—C23A—H23A	110.8	C24B—C25B—H25B	109.8
C22A—C23A—H23A	110.8	C26B—C25B—H25B	109.8
C24A—C23A—H23A	110.8	O10B—C26B—C27B	107.6 (5)
O8A—C24A—C25A	110.5 (6)	O10B—C26B—C25B	107.1 (5)
O8A—C24A—C23A	109.3 (5)	C27B—C26B—C25B	116.2 (5)
C25A—C24A—C23A	109.7 (5)	O10B—C26B—H26B	108.6
O8A—C24A—H24A	109.1	C27B—C26B—H26B	108.6
C25A—C24A—H24A	109.1	C25B—C26B—H26B	108.6
C23A—C24A—H24A	109.1	O11B—C27B—C26B	115.5 (6)
O9A—C25A—C24A	108.3 (6)	O11B—C27B—H27C	108.4
O9A—C25A—C26A	104.2 (5)	C26B—C27B—H27C	108.4
C24A—C25A—C26A	112.7 (6)	O11B—C27B—H27D	108.4
O9A—C25A—H25A	110.5	C26B—C27B—H27D	108.4
C24A—C25A—H25A	110.5	H27C—C27B—H27D	107.5
C26A—C25A—H25A	110.5

C6A—O1A—C1A—C7A	−168.1 (6)	C6B—O1B—C1B—C7B	−167.4 (6)
C6A—O1A—C1A—C2A	−43.8 (7)	C6B—O1B—C1B—C2B	−43.6 (7)
O1A—C1A—C2A—C3A	−83.8 (7)	O1B—C1B—C2B—C3B	−85.0 (7)
C7A—C1A—C2A—C3A	38.1 (9)	C7B—C1B—C2B—C3B	37.6 (8)
O1A—C1A—C2A—C5A	28.4 (7)	O1B—C1B—C2B—C5B	28.7 (7)
C7A—C1A—C2A—C5A	150.3 (6)	C7B—C1B—C2B—C5B	151.2 (6)
C4A—O2A—C3A—C2A	−42.6 (7)	C4B—O2B—C3B—C2B	−42.6 (7)
C1A—C2A—C3A—O2A	140.0 (6)	C1B—C2B—C3B—O2B	139.8 (6)
C5A—C2A—C3A—O2A	27.1 (7)	C5B—C2B—C3B—O2B	27.0 (7)
C3A—O2A—C4A—C15A	164.9 (6)	C3B—O2B—C4B—C15B	166.5 (6)
C3A—O2A—C4A—C5A	39.5 (6)	C3B—O2B—C4B—C5B	40.7 (6)
C3A—C2A—C5A—C6A	117.0 (7)	C3B—C2B—C5B—C6B	116.6 (6)
C1A—C2A—C5A—C6A	−3.9 (8)	C1B—C2B—C5B—C6B	−4.2 (7)
C3A—C2A—C5A—C4A	−3.1 (6)	C3B—C2B—C5B—C4B	−2.6 (6)
C1A—C2A—C5A—C4A	−124.0 (6)	C1B—C2B—C5B—C4B	−123.5 (6)
O2A—C4A—C5A—C6A	−133.8 (6)	O2B—C4B—C5B—C6B	−134.4 (6)
C15A—C4A—C5A—C6A	104.6 (7)	C15B—C4B—C5B—C6B	103.6 (7)
O2A—C4A—C5A—C2A	−21.6 (6)	O2B—C4B—C5B—C2B	−22.6 (6)
C15A—C4A—C5A—C2A	−143.1 (6)	C15B—C4B—C5B—C2B	−144.6 (6)
C1A—O1A—C6A—C5A	41.7 (8)	C1B—O1B—C6B—C5B	41.2 (8)
C2A—C5A—C6A—O1A	−21.9 (8)	C2B—C5B—C6B—O1B	−21.4 (8)
C4A—C5A—C6A—O1A	91.0 (7)	C4B—C5B—C6B—O1B	89.5 (7)
O1A—C1A—C7A—C12A	−169.3 (6)	O1B—C1B—C7B—C12B	−178.0 (6)
C2A—C1A—C7A—C12A	73.4 (9)	C2B—C1B—C7B—C12B	64.3 (9)
O1A—C1A—C7A—C8A	11.4 (9)	O1B—C1B—C7B—C8B	2.8 (9)
C2A—C1A—C7A—C8A	−106.0 (8)	C2B—C1B—C7B—C8B	−114.9 (7)
C12A—C7A—C8A—C9A	0.7 (10)	C12B—C7B—C8B—C9B	0.4 (10)
C1A—C7A—C8A—C9A	180.0 (6)	C1B—C7B—C8B—C9B	179.6 (6)
C7A—C8A—C9A—O3A	−179.9 (6)	C7B—C8B—C9B—O3B	179.6 (6)
C7A—C8A—C9A—C10A	−0.6 (10)	C7B—C8B—C9B—C10B	−0.3 (10)
C13A—O3A—C9A—C8A	2.9 (10)	C13B—O3B—C9B—C8B	6.7 (10)
C13A—O3A—C9A—C10A	−176.4 (6)	C13B—O3B—C9B—C10B	−173.4 (6)
C14A—O4A—C10A—C11A	−6.7 (11)	C14B—O4B—C10B—C11B	7.0 (11)
C14A—O4A—C10A—C9A	174.5 (7)	C14B—O4B—C10B—C9B	−172.5 (7)
C8A—C9A—C10A—O4A	179.5 (6)	C8B—C9B—C10B—C11B	0.5 (10)
O3A—C9A—C10A—O4A	−1.1 (9)	O3B—C9B—C10B—C11B	−179.4 (6)
C8A—C9A—C10A—C11A	0.7 (11)	C8B—C9B—C10B—O4B	−180.0 (6)
O3A—C9A—C10A—C11A	−180.0 (6)	O3B—C9B—C10B—O4B	0.1 (9)
O4A—C10A—C11A—C12A	−179.6 (7)	O4B—C10B—C11B—C12B	179.8 (7)
C9A—C10A—C11A—C12A	−0.8 (11)	C9B—C10B—C11B—C12B	−0.8 (11)
C8A—C7A—C12A—C11A	−0.8 (10)	C8B—C7B—C12B—C11B	−0.7 (11)
C1A—C7A—C12A—C11A	179.8 (6)	C1B—C7B—C12B—C11B	−179.9 (7)
C10A—C11A—C12A—C7A	1.0 (11)	C10B—C11B—C12B—C7B	0.9 (12)
O2A—C4A—C15A—C20A	−58.9 (9)	O2B—C4B—C15B—C20B	−56.3 (9)
C5A—C4A—C15A—C20A	59.4 (9)	C5B—C4B—C15B—C20B	63.0 (9)
O2A—C4A—C15A—C16A	121.2 (7)	O2B—C4B—C15B—C16B	123.3 (7)
C5A—C4A—C15A—C16A	−120.5 (7)	C5B—C4B—C15B—C16B	−117.3 (7)
C20A—C15A—C16A—C17A	0.0 (10)	C20B—C15B—C16B—C17B	0.8 (10)
C4A—C15A—C16A—C17A	179.9 (6)	C4B—C15B—C16B—C17B	−178.8 (6)
C21A—O5A—C17A—C16A	−0.8 (10)	C21B—O5B—C17B—C16B	−6.0 (10)
C21A—O5A—C17A—C18A	178.1 (6)	C21B—O5B—C17B—C18B	171.8 (6)
C15A—C16A—C17A—O5A	179.7 (7)	C15B—C16B—C17B—O5B	177.8 (6)
C15A—C16A—C17A—C18A	0.9 (10)	C15B—C16B—C17B—C18B	0.1 (10)
C22A—O6A—C18A—C19A	23.7 (9)	C22B—O6B—C18B—C19B	36.6 (9)
C22A—O6A—C18A—C17A	−156.3 (6)	C22B—O6B—C18B—C17B	−144.9 (6)
O5A—C17A—C18A—O6A	−0.7 (9)	O5B—C17B—C18B—C19B	−179.7 (6)
C16A—C17A—C18A—O6A	178.3 (6)	C16B—C17B—C18B—C19B	−1.7 (10)
O5A—C17A—C18A—C19A	179.4 (6)	O5B—C17B—C18B—O6B	1.7 (8)
C16A—C17A—C18A—C19A	−1.7 (10)	C16B—C17B—C18B—O6B	179.7 (6)
O6A—C18A—C19A—C20A	−178.4 (6)	O6B—C18B—C19B—C20B	−179.2 (6)
C17A—C18A—C19A—C20A	1.5 (10)	C17B—C18B—C19B—C20B	2.4 (10)
C16A—C15A—C20A—C19A	−0.2 (10)	C16B—C15B—C20B—C19B	−0.2 (10)
C4A—C15A—C20A—C19A	180.0 (6)	C4B—C15B—C20B—C19B	179.5 (7)
C18A—C19A—C20A—C15A	−0.6 (10)	C18B—C19B—C20B—C15B	−1.5 (11)
C18A—O6A—C22A—O10A	−90.9 (6)	C18B—O6B—C22B—O10B	−88.6 (6)
C18A—O6A—C22A—C23A	152.1 (5)	C18B—O6B—C22B—C23B	151.9 (5)
C26A—O10A—C22A—O6A	177.8 (4)	C26B—O10B—C22B—O6B	173.5 (4)
C26A—O10A—C22A—C23A	−65.1 (6)	C26B—O10B—C22B—C23B	−68.1 (6)
O6A—C22A—C23A—O7A	−66.7 (7)	O6B—C22B—C23B—O7B	−68.1 (7)
O10A—C22A—C23A—O7A	178.2 (5)	O10B—C22B—C23B—O7B	174.1 (5)
O6A—C22A—C23A—C24A	176.9 (5)	O6B—C22B—C23B—C24B	173.6 (5)
O10A—C22A—C23A—C24A	61.7 (7)	O10B—C22B—C23B—C24B	55.8 (7)
O7A—C23A—C24A—O8A	65.6 (7)	O7B—C23B—C24B—O8B	70.1 (6)
C22A—C23A—C24A—O8A	−177.5 (6)	C22B—C23B—C24B—O8B	−169.9 (5)
O7A—C23A—C24A—C25A	−173.2 (6)	O7B—C23B—C24B—C25B	−167.6 (5)
C22A—C23A—C24A—C25A	−56.2 (7)	C22B—C23B—C24B—C25B	−47.7 (7)
O8A—C24A—C25A—O9A	−71.0 (7)	O8B—C24B—C25B—O9B	−69.5 (6)
C23A—C24A—C25A—O9A	168.5 (5)	C23B—C24B—C25B—O9B	168.4 (5)
O8A—C24A—C25A—C26A	174.3 (5)	O8B—C24B—C25B—C26B	172.5 (5)
C23A—C24A—C25A—C26A	53.8 (8)	C23B—C24B—C25B—C26B	50.3 (7)
C22A—O10A—C26A—C25A	59.8 (7)	C22B—O10B—C26B—C27B	−165.5 (5)
C22A—O10A—C26A—C27A	178.7 (5)	C22B—O10B—C26B—C25B	68.9 (6)
O9A—C25A—C26A—O10A	−171.7 (5)	O9B—C25B—C26B—O10B	−179.2 (5)
C24A—C25A—C26A—O10A	−54.4 (8)	C24B—C25B—C26B—O10B	−59.6 (7)
O9A—C25A—C26A—C27A	71.0 (7)	O9B—C25B—C26B—C27B	60.5 (7)
C24A—C25A—C26A—C27A	−171.8 (6)	C24B—C25B—C26B—C27B	−179.8 (6)
O10A—C26A—C27A—O11A	83.9 (7)	O10B—C26B—C27B—O11B	−76.5 (7)
C25A—C26A—C27A—O11A	−158.2 (6)	C25B—C26B—C27B—O11B	43.5 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7A—H7AA···O14ⁱ	0.82	1.77	2.591 (9)	177
O8A—H8AA···O11Bⁱⁱ	0.82	2.12	2.913 (6)	163
O9A—H9AA···O13ⁱⁱⁱ	0.82	2.01	2.795 (6)	160
O11A—H11A···O4B	0.82	1.99	2.809 (7)	178
O7B—H7BA···O12^iv	0.82	2.03	2.830 (7)	163
O8B—H8BA···O9A^v	0.82	1.96	2.766 (7)	169
O9B—H9BA···O12^vi	0.82	1.96	2.782 (6)	180
O11B—H11B···O8B^vii	0.82	2.00	2.765 (6)	155
O12—H28···O11A^viii	0.86	2.09	2.886 (8)	154
O12—H29···O7A^ix	0.86	2.03	2.783 (7)	146
O13—H30···O7B	0.86	2.07	2.873 (7)	155
O13—H31···O11Bⁱ	0.86	2.36	2.837 (7)	115
O14—H32···O5A^x	0.86	2.03	2.794 (9)	147
O14—H32···O6A^x	0.86	2.39	3.111 (9)	141
O14—H33···O13^xi	0.86	1.90	2.683 (9)	151

Symmetry codes: (i) x, y+1, z; (ii) x−1, y+1, z−1; (iii) x−1, y, z−1; (iv) −x+1, y+1/2, −z+1; (v) x+1, y, z+1; (vi) x, y, z+1; (vii) −x+1, y−1/2, −z+2; (viii) x+1, y, z; (ix) x+1, y−1, z; (x) x, y−1, z; (xi) −x+1, y−1/2, −z+1.

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