(3aS*,10R*,10aS*,10bS*,13R*,13aR*)-8-Formyl-6-hydroxy-13-methoxy-1,1,7-tri­methyl-5-oxo-1,2,3,3a,5,9,10,10a,13,13a-deca­hydro­cyclo­hepta­[c]­furo­[3,4-e]­chromen-10-yl acetate

The title compound, C₂₃H₃₀O₈, was prepared from macrocalyxin A and its structure was established from the ESI-MS, ¹H NMR, ¹³C NMR and X-ray crystallographic data. Two unique mol­ecules are present in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.048
• wR factor = 0.119
• Data-to-parameter ratio = 8.8

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:      0.724     0.980
            Tmin' and Tmax expected:      0.953     0.978
            RR' =      0.758
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.76
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.06 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.83 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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           26.99
           From the CIF: _reflns_number_total               4997
           Count of symmetry unique reflns         5043
           Completeness (_total/calc)             99.09%
           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

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   2 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

---

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(3aS,10R,10aS,10bS,13R,13aR)-8-formyl-6-hydroxy-13-methoxy-1,1,7-trimethyl- 5-oxo-1,2,3,3a,5,9,10,10a,13,13a-decahydrocyclohepta[c]furo[3,4-e]chromen-10-yl acetate

Crystal data

C23H30O8	F(000) = 928
Mr = 434.47	Dx = 1.300 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 11.6288 (9) Å	Cell parameters from 4360 reflections
b = 14.0386 (11) Å	θ = 4.3–46.5°
c = 13.7457 (10) Å	µ = 0.10 mm^−1
β = 98.349 (1)°	T = 293 K
V = 2220.2 (3) Å^3	Block, colorless
Z = 4	0.48 × 0.35 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4997 independent reflections
Radiation source: fine-focus sealed tube	4028 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
φ and ω scans	θmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −14→14
Tmin = 0.724, Tmax = 0.980	k = −17→17
13086 measured reflections	l = −17→11

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 0.84	w = 1/[σ^2(Fo^2) + (0.0814P)^2] where P = (Fo^2 + 2Fc^2)/3
4997 reflections	(Δ/σ)max < 0.001
571 parameters	Δρmax = 0.26 e Å^−3
1 restraint	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
O1	0.3439 (3)	0.08533 (18)	−0.0610 (2)	0.0748 (8)
C1	−0.0282 (3)	0.3280 (3)	0.1327 (3)	0.0612 (10)
O2	0.1967 (2)	0.12941 (16)	0.0106 (2)	0.0602 (6)
C2	−0.0729 (4)	0.2378 (3)	0.0804 (4)	0.0749 (12)
H2A	−0.1076	0.2538	0.0140	0.090*
H2B	−0.1335	0.2113	0.1138	0.090*
O3	0.1915 (2)	0.50800 (16)	0.09138 (17)	0.0499 (5)
C3A	0.1089 (3)	0.2021 (2)	0.0183 (3)	0.0501 (8)
H3C	0.0694	0.2146	−0.0484	0.060*
C3	0.0204 (4)	0.1619 (3)	0.0756 (3)	0.0678 (10)
H3A	0.0567	0.1451	0.1414	0.081*
H3B	−0.0141	0.1050	0.0437	0.081*
O4	0.2455 (2)	0.38109 (17)	0.19852 (16)	0.0528 (6)
O5	0.0048 (3)	0.4686 (2)	−0.2259 (3)	0.0982 (12)
C5	0.2847 (3)	0.1521 (2)	−0.0366 (3)	0.0525 (8)
C5A	0.3135 (3)	0.2507 (2)	−0.0516 (2)	0.0400 (6)
O6	0.08733 (19)	0.33668 (16)	−0.15674 (15)	0.0464 (5)
C6	0.4140 (3)	0.2694 (2)	−0.0885 (2)	0.0457 (7)
O7	0.3672 (4)	0.6034 (2)	−0.1570 (3)	0.0996 (11)
C7	0.4611 (3)	0.3667 (3)	−0.0944 (2)	0.0467 (7)
O8	0.4844 (2)	0.2017 (2)	−0.1144 (2)	0.0647 (7)
H8O	0.4612	0.1493	−0.0994	0.097*
C8	0.3891 (3)	0.4378 (2)	−0.1288 (2)	0.0465 (7)
C9	0.2659 (3)	0.4187 (2)	−0.1752 (2)	0.0451 (7)
H9A	0.2666	0.3675	−0.2225	0.054*
H9B	0.2364	0.4751	−0.2113	0.054*
C10	0.1814 (2)	0.3920 (2)	−0.1043 (2)	0.0367 (6)
H10	0.1500	0.4502	−0.0788	0.044*
C10A	0.2419 (2)	0.3322 (2)	−0.01798 (19)	0.0333 (6)
H10A	0.2984	0.3751	0.0195	0.040*
C10B	0.1648 (2)	0.2946 (2)	0.0572 (2)	0.0380 (6)
C11	0.2453 (3)	0.2866 (2)	0.1564 (2)	0.0448 (7)
H11A	0.2155	0.2403	0.1987	0.054*
H11B	0.3231	0.2680	0.1466	0.054*
C13A	0.0754 (3)	0.3681 (2)	0.0840 (2)	0.0438 (7)
H13A	0.0434	0.4026	0.0241	0.053*
C13	0.1523 (3)	0.4353 (3)	0.1499 (2)	0.0475 (7)
H13	0.1083	0.4636	0.1983	0.057*
C14	0.0015 (4)	0.3055 (4)	0.2437 (3)	0.0834 (14)
H14A	0.0290	0.3622	0.2785	0.125*
H14B	0.0608	0.2574	0.2533	0.125*
H14C	−0.0668	0.2829	0.2680	0.125*
C15	−0.1236 (4)	0.4036 (4)	0.1196 (4)	0.0840 (14)
H15A	−0.1892	0.3814	0.1483	0.126*
H15B	−0.1470	0.4155	0.0508	0.126*
H15C	−0.0947	0.4614	0.1516	0.126*
C16	0.5902 (3)	0.3736 (3)	−0.0593 (3)	0.0648 (10)
H16A	0.6322	0.3560	−0.1117	0.097*
H16B	0.6107	0.3314	−0.0046	0.097*
H16C	0.6096	0.4378	−0.0392	0.097*
C17	0.4280 (4)	0.5373 (3)	−0.1261 (3)	0.0666 (10)
H17	0.5043	0.5502	−0.0988	0.080*
C18	0.0031 (3)	0.3841 (3)	−0.2136 (3)	0.0652 (10)
C19	−0.0883 (4)	0.3168 (4)	−0.2603 (4)	0.1017 (18)
H19A	−0.1354	0.2965	−0.2123	0.153*
H19B	−0.0519	0.2624	−0.2852	0.153*
H19C	−0.1363	0.3483	−0.3134	0.153*
C20	0.2586 (4)	0.5808 (3)	0.1457 (3)	0.0724 (11)
H20A	0.2148	0.6078	0.1930	0.109*
H20B	0.2767	0.6297	0.1015	0.109*
H20C	0.3294	0.5539	0.1791	0.109*
O21	0.4719 (2)	0.84493 (19)	0.3349 (2)	0.0696 (8)
C21	0.8807 (3)	0.5521 (2)	0.4578 (2)	0.0424 (7)
O22	0.6252 (2)	0.75642 (16)	0.33355 (16)	0.0485 (5)
C22	0.8626 (3)	0.5781 (3)	0.3484 (2)	0.0504 (8)
H22A	0.9375	0.5798	0.3253	0.061*
H22B	0.8163	0.5289	0.3119	0.061*
O23	0.68049 (18)	0.51365 (15)	0.64072 (14)	0.0405 (5)
C23A	0.6814 (3)	0.6653 (2)	0.3541 (2)	0.0391 (6)
H23C	0.6388	0.6178	0.3108	0.047*
C23	0.8028 (3)	0.6734 (2)	0.3272 (3)	0.0500 (8)
H23A	0.8457	0.7231	0.3658	0.060*
H23B	0.7990	0.6892	0.2581	0.060*
O24	0.76798 (19)	0.66155 (14)	0.62473 (14)	0.0434 (5)
O25	0.4926 (2)	0.34137 (17)	0.35901 (19)	0.0585 (6)
C25	0.5213 (3)	0.7709 (2)	0.3629 (2)	0.0461 (7)
C25A	0.4753 (3)	0.7019 (2)	0.4263 (2)	0.0379 (6)
O26	0.52076 (19)	0.49763 (15)	0.33584 (15)	0.0418 (5)
C26	0.3732 (3)	0.7241 (2)	0.4591 (2)	0.0402 (7)
O27	0.2342 (3)	0.42373 (19)	0.5600 (2)	0.0719 (8)
C27	0.3196 (2)	0.6622 (2)	0.5272 (2)	0.0391 (6)
O28	0.3138 (2)	0.80440 (16)	0.43601 (19)	0.0527 (6)
H28O	0.3474	0.8364	0.3989	0.079*
C28	0.3169 (2)	0.5670 (2)	0.5125 (2)	0.0384 (6)
C29	0.3621 (3)	0.5210 (2)	0.4265 (2)	0.0412 (7)
H29A	0.3301	0.5546	0.3670	0.049*
H29B	0.3339	0.4560	0.4205	0.049*
C30	0.4938 (2)	0.5199 (2)	0.4337 (2)	0.0358 (6)
H30	0.5255	0.4700	0.4798	0.043*
C30A	0.5467 (2)	0.61596 (19)	0.46849 (19)	0.0317 (5)
H30A	0.5425	0.6176	0.5392	0.038*
C30B	0.6767 (2)	0.63547 (19)	0.46055 (19)	0.0322 (6)
C31	0.7194 (3)	0.7122 (2)	0.5375 (2)	0.0377 (6)
H31A	0.7779	0.7521	0.5143	0.045*
H31B	0.6553	0.7521	0.5505	0.045*
C33A	0.7599 (2)	0.5521 (2)	0.49593 (19)	0.0331 (6)
H33A	0.7203	0.4917	0.4774	0.040*
C33	0.7726 (2)	0.5632 (2)	0.6067 (2)	0.0374 (6)
H33	0.8475	0.5372	0.6373	0.045*
C34	0.9299 (3)	0.4505 (3)	0.4704 (3)	0.0595 (9)
H34A	1.0035	0.4479	0.4465	0.089*
H34B	0.8768	0.4068	0.4337	0.089*
H34C	0.9403	0.4335	0.5387	0.089*
C35	0.9710 (3)	0.6192 (3)	0.5136 (3)	0.0564 (9)
H35A	1.0409	0.6173	0.4842	0.085*
H35B	0.9876	0.5994	0.5810	0.085*
H35C	0.9409	0.6830	0.5106	0.085*
C36	0.2670 (3)	0.7132 (3)	0.6069 (3)	0.0543 (8)
H36A	0.1846	0.7025	0.5978	0.081*
H36B	0.2821	0.7803	0.6035	0.081*
H36C	0.3009	0.6893	0.6700	0.081*
C37	0.2600 (3)	0.5040 (3)	0.5765 (3)	0.0485 (7)
H37	0.2429	0.5297	0.6351	0.058*
C38	0.5169 (3)	0.4056 (2)	0.3082 (2)	0.0437 (7)
C39	0.5469 (4)	0.3948 (3)	0.2065 (3)	0.0645 (10)
H39A	0.6097	0.4370	0.1981	0.097*
H39B	0.4803	0.4101	0.1593	0.097*
H39C	0.5701	0.3302	0.1969	0.097*
C40	0.6740 (4)	0.5290 (3)	0.7418 (3)	0.0679 (11)
H40A	0.7500	0.5224	0.7792	0.102*
H40B	0.6226	0.4829	0.7640	0.102*
H40C	0.6450	0.5919	0.7506	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.087 (2)	0.0420 (14)	0.093 (2)	0.0222 (14)	0.0070 (16)	−0.0060 (13)
C1	0.0440 (18)	0.086 (3)	0.057 (2)	0.0007 (19)	0.0197 (17)	0.0111 (19)
O2	0.0713 (16)	0.0379 (12)	0.0712 (17)	0.0002 (11)	0.0097 (13)	0.0067 (11)
C2	0.051 (2)	0.088 (3)	0.088 (3)	−0.016 (2)	0.019 (2)	0.014 (2)
O3	0.0588 (14)	0.0480 (12)	0.0422 (11)	0.0021 (11)	0.0049 (10)	−0.0030 (10)
C3A	0.0526 (19)	0.0440 (17)	0.0517 (18)	0.0005 (15)	0.0010 (15)	0.0066 (15)
C3	0.066 (2)	0.057 (2)	0.079 (3)	−0.0194 (19)	0.006 (2)	0.012 (2)
O4	0.0571 (14)	0.0611 (14)	0.0363 (12)	0.0073 (11)	−0.0059 (10)	−0.0016 (10)
O5	0.091 (2)	0.073 (2)	0.110 (3)	0.0238 (18)	−0.052 (2)	0.0048 (18)
C5	0.060 (2)	0.0419 (18)	0.0520 (19)	0.0132 (16)	−0.0052 (16)	−0.0020 (15)
C5A	0.0413 (16)	0.0441 (16)	0.0321 (14)	0.0081 (13)	−0.0027 (12)	−0.0012 (12)
O6	0.0452 (11)	0.0497 (12)	0.0401 (11)	0.0049 (10)	−0.0078 (9)	0.0025 (9)
C6	0.0464 (17)	0.0539 (18)	0.0358 (15)	0.0136 (15)	0.0026 (13)	−0.0065 (13)
O7	0.105 (3)	0.066 (2)	0.124 (3)	−0.003 (2)	0.007 (2)	0.020 (2)
C7	0.0435 (16)	0.066 (2)	0.0329 (15)	0.0034 (15)	0.0134 (13)	−0.0043 (14)
O8	0.0592 (15)	0.0691 (16)	0.0676 (17)	0.0266 (14)	0.0153 (13)	−0.0089 (14)
C8	0.0510 (18)	0.061 (2)	0.0306 (15)	0.0021 (16)	0.0150 (13)	0.0030 (14)
C9	0.0524 (18)	0.0525 (18)	0.0300 (14)	0.0069 (15)	0.0045 (13)	0.0061 (13)
C10	0.0417 (15)	0.0368 (14)	0.0302 (14)	0.0082 (12)	0.0003 (12)	−0.0005 (11)
C10A	0.0362 (13)	0.0347 (14)	0.0275 (13)	0.0042 (12)	−0.0003 (11)	0.0007 (11)
C10B	0.0350 (14)	0.0436 (16)	0.0339 (14)	0.0023 (12)	0.0006 (12)	0.0086 (12)
C11	0.0483 (17)	0.0489 (18)	0.0359 (15)	0.0034 (14)	0.0013 (13)	0.0106 (13)
C13A	0.0395 (15)	0.0551 (18)	0.0377 (16)	0.0060 (14)	0.0083 (13)	0.0085 (13)
C13	0.0462 (17)	0.061 (2)	0.0365 (16)	0.0089 (15)	0.0090 (14)	−0.0056 (14)
C14	0.070 (3)	0.127 (4)	0.060 (2)	0.002 (3)	0.033 (2)	0.022 (3)
C15	0.053 (2)	0.114 (4)	0.091 (3)	0.014 (2)	0.031 (2)	0.009 (3)
C16	0.0436 (18)	0.093 (3)	0.059 (2)	0.0020 (19)	0.0105 (16)	0.001 (2)
C17	0.070 (3)	0.066 (3)	0.064 (2)	−0.007 (2)	0.013 (2)	0.0091 (19)
C18	0.058 (2)	0.069 (3)	0.061 (2)	0.0121 (19)	−0.0197 (18)	−0.0009 (19)
C19	0.074 (3)	0.118 (4)	0.097 (4)	−0.015 (3)	−0.044 (3)	0.009 (3)
C20	0.086 (3)	0.055 (2)	0.070 (3)	−0.007 (2)	−0.008 (2)	−0.0064 (19)
O21	0.0675 (16)	0.0635 (16)	0.0814 (19)	0.0236 (14)	0.0225 (14)	0.0374 (14)
C21	0.0336 (14)	0.0484 (17)	0.0465 (17)	0.0017 (13)	0.0102 (13)	0.0017 (13)
O22	0.0507 (13)	0.0504 (13)	0.0469 (12)	0.0052 (10)	0.0152 (10)	0.0168 (10)
C22	0.0445 (17)	0.061 (2)	0.0496 (19)	0.0006 (15)	0.0211 (15)	−0.0006 (15)
O23	0.0467 (11)	0.0441 (11)	0.0319 (10)	−0.0042 (9)	0.0092 (9)	0.0022 (8)
C23A	0.0385 (15)	0.0449 (15)	0.0349 (14)	−0.0008 (12)	0.0088 (12)	0.0065 (13)
C23	0.0497 (18)	0.059 (2)	0.0451 (17)	−0.0036 (15)	0.0200 (15)	0.0083 (15)
O24	0.0527 (12)	0.0393 (11)	0.0357 (11)	−0.0047 (10)	−0.0024 (9)	−0.0030 (9)
O25	0.0676 (16)	0.0452 (13)	0.0654 (16)	0.0002 (12)	0.0192 (13)	0.0003 (11)
C25	0.0450 (17)	0.0488 (17)	0.0445 (17)	0.0069 (15)	0.0063 (14)	0.0113 (14)
C25A	0.0380 (15)	0.0409 (15)	0.0341 (14)	0.0016 (13)	0.0029 (12)	0.0037 (12)
O26	0.0465 (12)	0.0412 (11)	0.0396 (11)	−0.0031 (9)	0.0124 (9)	−0.0026 (9)
C26	0.0381 (15)	0.0415 (16)	0.0392 (15)	0.0047 (13)	−0.0006 (13)	0.0031 (12)
O27	0.0789 (19)	0.0525 (16)	0.090 (2)	−0.0039 (14)	0.0318 (16)	0.0057 (14)
C27	0.0294 (14)	0.0498 (17)	0.0369 (15)	0.0034 (12)	0.0003 (12)	0.0004 (13)
O28	0.0438 (12)	0.0517 (13)	0.0620 (15)	0.0151 (10)	0.0054 (10)	0.0124 (11)
C28	0.0295 (14)	0.0469 (17)	0.0371 (15)	0.0029 (12)	−0.0014 (12)	0.0001 (13)
C29	0.0330 (14)	0.0500 (17)	0.0395 (16)	−0.0016 (13)	0.0011 (12)	−0.0050 (13)
C30	0.0349 (14)	0.0396 (15)	0.0336 (14)	0.0017 (12)	0.0076 (11)	0.0007 (12)
C30A	0.0315 (13)	0.0359 (14)	0.0279 (13)	0.0014 (11)	0.0055 (10)	0.0024 (11)
C30B	0.0322 (13)	0.0342 (14)	0.0306 (14)	0.0016 (11)	0.0056 (11)	0.0015 (10)
C31	0.0365 (14)	0.0350 (14)	0.0417 (15)	0.0001 (12)	0.0058 (12)	0.0013 (12)
C33A	0.0334 (13)	0.0347 (14)	0.0307 (13)	0.0005 (11)	0.0032 (11)	−0.0016 (11)
C33	0.0339 (14)	0.0387 (15)	0.0369 (15)	0.0013 (12)	−0.0040 (12)	0.0025 (12)
C34	0.0465 (18)	0.060 (2)	0.076 (3)	0.0145 (16)	0.0209 (18)	0.0006 (19)
C35	0.0349 (15)	0.071 (2)	0.064 (2)	−0.0042 (16)	0.0070 (15)	−0.0027 (18)
C36	0.0501 (19)	0.058 (2)	0.058 (2)	0.0047 (16)	0.0186 (16)	−0.0074 (16)
C37	0.0482 (18)	0.0475 (19)	0.0516 (19)	0.0064 (15)	0.0138 (15)	0.0058 (15)
C38	0.0336 (14)	0.0494 (18)	0.0479 (17)	0.0010 (13)	0.0058 (13)	−0.0084 (14)
C39	0.066 (2)	0.072 (2)	0.061 (2)	−0.011 (2)	0.0284 (19)	−0.0215 (19)
C40	0.097 (3)	0.069 (2)	0.0417 (19)	−0.023 (2)	0.023 (2)	−0.0095 (16)

Geometric parameters (Å, º)

O1—C5	1.239 (4)	O21—C25	1.223 (4)
C1—C2	1.510 (6)	C21—C35	1.531 (5)
C1—C15	1.527 (6)	C21—C22	1.532 (5)
C1—C14	1.547 (6)	C21—C34	1.537 (5)
C1—C13A	1.565 (4)	C21—C33A	1.569 (4)
O2—C5	1.327 (4)	O22—C25	1.344 (4)
O2—C3A	1.458 (4)	O22—C23A	1.445 (4)
C2—C3	1.530 (6)	C22—C23	1.516 (5)
C2—H2A	0.9700	C22—H22A	0.9700
C2—H2B	0.9700	C22—H22B	0.9700
O3—C13	1.415 (4)	O23—C33	1.413 (4)
O3—C20	1.429 (5)	O23—C40	1.419 (4)
C3A—C3	1.495 (5)	C23A—C23	1.515 (4)
C3A—C10B	1.515 (5)	C23A—C30B	1.530 (4)
C3A—H3C	0.9800	C23A—H23C	0.9800
C3—H3A	0.9700	C23—H23A	0.9700
C3—H3B	0.9700	C23—H23B	0.9700
O4—C13	1.411 (4)	O24—C33	1.406 (3)
O4—C11	1.447 (4)	O24—C31	1.437 (4)
O5—C18	1.198 (5)	O25—C38	1.200 (4)
C5—C5A	1.446 (5)	C25—C25A	1.456 (4)
C5A—C6	1.365 (5)	C25A—C26	1.366 (4)
C5A—C10A	1.525 (4)	C25A—C30A	1.530 (4)
O6—C18	1.338 (4)	O26—C38	1.345 (4)
O6—C10	1.446 (4)	O26—C30	1.459 (3)
C6—O8	1.336 (4)	C26—O28	1.335 (4)
C6—C7	1.479 (5)	C26—C27	1.480 (4)
O7—C17	1.206 (5)	O27—C37	1.180 (4)
C7—C8	1.344 (5)	C27—C28	1.351 (4)
C7—C16	1.511 (5)	C27—C36	1.511 (4)
O8—H8O	0.8200	O28—H28O	0.8200
C8—C17	1.468 (5)	C28—C37	1.470 (4)
C8—C9	1.505 (5)	C28—C29	1.507 (4)
C9—C10	1.527 (4)	C29—C30	1.520 (4)
C9—H9A	0.9700	C29—H29A	0.9700
C9—H9B	0.9700	C29—H29B	0.9700
C10—C10A	1.539 (4)	C30—C30A	1.531 (4)
C10—H10	0.9800	C30—H30	0.9800
C10A—C10B	1.555 (4)	C30A—C30B	1.555 (4)
C10A—H10A	0.9800	C30A—H30A	0.9800
C10B—C11	1.541 (4)	C30B—C31	1.540 (4)
C10B—C13A	1.547 (4)	C30B—C33A	1.551 (4)
C11—H11A	0.9700	C31—H31A	0.9700
C11—H11B	0.9700	C31—H31B	0.9700
C13A—C13	1.509 (5)	C33A—C33	1.516 (4)
C13A—H13A	0.9800	C33A—H33A	0.9800
C13—H13	0.9800	C33—H33	0.9800
C14—H14A	0.9600	C34—H34A	0.9600
C14—H14B	0.9600	C34—H34B	0.9600
C14—H14C	0.9600	C34—H34C	0.9600
C15—H15A	0.9600	C35—H35A	0.9600
C15—H15B	0.9600	C35—H35B	0.9600
C15—H15C	0.9600	C35—H35C	0.9600
C16—H16A	0.9600	C36—H36A	0.9600
C16—H16B	0.9600	C36—H36B	0.9600
C16—H16C	0.9600	C36—H36C	0.9600
C17—H17	0.9300	C37—H37	0.9300
C18—C19	1.496 (6)	C38—C39	1.497 (5)
C19—H19A	0.9600	C39—H39A	0.9600
C19—H19B	0.9600	C39—H39B	0.9600
C19—H19C	0.9600	C39—H39C	0.9600
C20—H20A	0.9600	C40—H40A	0.9600
C20—H20B	0.9600	C40—H40B	0.9600
C20—H20C	0.9600	C40—H40C	0.9600
C2—C1—C15	109.4 (4)	C35—C21—C22	109.4 (3)
C2—C1—C14	108.0 (4)	C35—C21—C34	107.3 (3)
C15—C1—C14	108.2 (4)	C22—C21—C34	109.1 (3)
C2—C1—C13A	109.4 (3)	C35—C21—C33A	114.5 (2)
C15—C1—C13A	107.0 (3)	C22—C21—C33A	109.0 (2)
C14—C1—C13A	114.8 (3)	C34—C21—C33A	107.4 (2)
C5—O2—C3A	117.7 (2)	C25—O22—C23A	118.4 (2)
C1—C2—C3	114.0 (3)	C23—C22—C21	113.1 (3)
C1—C2—H2A	108.7	C23—C22—H22A	109.0
C3—C2—H2A	108.7	C21—C22—H22A	109.0
C1—C2—H2B	108.7	C23—C22—H22B	109.0
C3—C2—H2B	108.7	C21—C22—H22B	109.0
H2A—C2—H2B	107.6	H22A—C22—H22B	107.8
C13—O3—C20	114.5 (3)	C33—O23—C40	113.6 (2)
O2—C3A—C3	108.5 (3)	O22—C23A—C23	107.3 (2)
O2—C3A—C10B	110.9 (3)	O22—C23A—C30B	110.6 (2)
C3—C3A—C10B	115.5 (3)	C23—C23A—C30B	114.7 (3)
O2—C3A—H3C	107.2	O22—C23A—H23C	108.0
C3—C3A—H3C	107.2	C23—C23A—H23C	108.0
C10B—C3A—H3C	107.2	C30B—C23A—H23C	108.0
C3A—C3—C2	107.8 (3)	C23A—C23—C22	107.7 (2)
C3A—C3—H3A	110.1	C23A—C23—H23A	110.2
C2—C3—H3A	110.1	C22—C23—H23A	110.2
C3A—C3—H3B	110.1	C23A—C23—H23B	110.2
C2—C3—H3B	110.1	C22—C23—H23B	110.2
H3A—C3—H3B	108.5	H23A—C23—H23B	108.5
C13—O4—C11	110.4 (2)	C33—O24—C31	111.0 (2)
O1—C5—O2	116.7 (3)	O21—C25—O22	115.8 (3)
O1—C5—C5A	122.4 (4)	O21—C25—C25A	123.9 (3)
O2—C5—C5A	120.7 (3)	O22—C25—C25A	120.2 (3)
C6—C5A—C5	117.7 (3)	C26—C25A—C25	117.2 (3)
C6—C5A—C10A	120.2 (3)	C26—C25A—C30A	120.4 (3)
C5—C5A—C10A	121.8 (3)	C25—C25A—C30A	121.7 (2)
C18—O6—C10	117.4 (3)	C38—O26—C30	117.6 (2)
O8—C6—C5A	123.6 (3)	O28—C26—C25A	124.0 (3)
O8—C6—C7	113.3 (3)	O28—C26—C27	113.3 (3)
C5A—C6—C7	122.8 (3)	C25A—C26—C27	122.7 (3)
C8—C7—C6	119.2 (3)	C28—C27—C26	119.3 (3)
C8—C7—C16	127.2 (3)	C28—C27—C36	125.0 (3)
C6—C7—C16	113.6 (3)	C26—C27—C36	115.6 (3)
C6—O8—H8O	109.5	C26—O28—H28O	109.5
C7—C8—C17	121.6 (3)	C27—C28—C37	120.6 (3)
C7—C8—C9	121.6 (3)	C27—C28—C29	122.5 (3)
C17—C8—C9	116.8 (3)	C37—C28—C29	116.7 (3)
C8—C9—C10	115.7 (2)	C28—C29—C30	114.6 (2)
C8—C9—H9A	108.3	C28—C29—H29A	108.6
C10—C9—H9A	108.3	C30—C29—H29A	108.6
C8—C9—H9B	108.3	C28—C29—H29B	108.6
C10—C9—H9B	108.3	C30—C29—H29B	108.6
H9A—C9—H9B	107.4	H29A—C29—H29B	107.6
O6—C10—C9	108.9 (2)	O26—C30—C29	107.0 (2)
O6—C10—C10A	108.6 (2)	O26—C30—C30A	110.2 (2)
C9—C10—C10A	111.2 (2)	C29—C30—C30A	111.5 (2)
O6—C10—H10	109.4	O26—C30—H30	109.4
C9—C10—H10	109.4	C29—C30—H30	109.4
C10A—C10—H10	109.4	C30A—C30—H30	109.4
C5A—C10A—C10	112.6 (2)	C25A—C30A—C30	113.9 (2)
C5A—C10A—C10B	109.9 (2)	C25A—C30A—C30B	108.3 (2)
C10—C10A—C10B	117.0 (2)	C30—C30A—C30B	119.0 (2)
C5A—C10A—H10A	105.4	C25A—C30A—H30A	104.7
C10—C10A—H10A	105.4	C30—C30A—H30A	104.7
C10B—C10A—H10A	105.4	C30B—C30A—H30A	104.7
C3A—C10B—C11	115.1 (3)	C23A—C30B—C31	114.3 (2)
C3A—C10B—C13A	112.7 (2)	C23A—C30B—C33A	113.5 (2)
C11—C10B—C13A	100.4 (2)	C31—C30B—C33A	100.8 (2)
C3A—C10B—C10A	108.4 (2)	C23A—C30B—C30A	106.6 (2)
C11—C10B—C10A	106.1 (2)	C31—C30B—C30A	107.2 (2)
C13A—C10B—C10A	113.9 (2)	C33A—C30B—C30A	114.4 (2)
O4—C11—C10B	104.7 (2)	O24—C31—C30B	106.0 (2)
O4—C11—H11A	110.8	O24—C31—H31A	110.5
C10B—C11—H11A	110.8	C30B—C31—H31A	110.5
O4—C11—H11B	110.8	O24—C31—H31B	110.5
C10B—C11—H11B	110.8	C30B—C31—H31B	110.5
H11A—C11—H11B	108.9	H31A—C31—H31B	108.7
C13—C13A—C10B	101.5 (2)	C33—C33A—C30B	101.7 (2)
C13—C13A—C1	113.2 (3)	C33—C33A—C21	112.0 (2)
C10B—C13A—C1	116.6 (3)	C30B—C33A—C21	116.3 (2)
C13—C13A—H13A	108.4	C33—C33A—H33A	108.8
C10B—C13A—H13A	108.4	C30B—C33A—H33A	108.8
C1—C13A—H13A	108.4	C21—C33A—H33A	108.8
O4—C13—O3	111.7 (3)	O24—C33—O23	112.0 (2)
O4—C13—C13A	107.1 (3)	O24—C33—C33A	106.1 (2)
O3—C13—C13A	108.7 (2)	O23—C33—C33A	108.3 (2)
O4—C13—H13	109.8	O24—C33—H33	110.1
O3—C13—H13	109.8	O23—C33—H33	110.1
C13A—C13—H13	109.8	C33A—C33—H33	110.1
C1—C14—H14A	109.5	C21—C34—H34A	109.5
C1—C14—H14B	109.5	C21—C34—H34B	109.5
H14A—C14—H14B	109.5	H34A—C34—H34B	109.5
C1—C14—H14C	109.5	C21—C34—H34C	109.5
H14A—C14—H14C	109.5	H34A—C34—H34C	109.5
H14B—C14—H14C	109.5	H34B—C34—H34C	109.5
C1—C15—H15A	109.5	C21—C35—H35A	109.5
C1—C15—H15B	109.5	C21—C35—H35B	109.5
H15A—C15—H15B	109.5	H35A—C35—H35B	109.5
C1—C15—H15C	109.5	C21—C35—H35C	109.5
H15A—C15—H15C	109.5	H35A—C35—H35C	109.5
H15B—C15—H15C	109.5	H35B—C35—H35C	109.5
C7—C16—H16A	109.5	C27—C36—H36A	109.5
C7—C16—H16B	109.5	C27—C36—H36B	109.5
H16A—C16—H16B	109.5	H36A—C36—H36B	109.5
C7—C16—H16C	109.5	C27—C36—H36C	109.5
H16A—C16—H16C	109.5	H36A—C36—H36C	109.5
H16B—C16—H16C	109.5	H36B—C36—H36C	109.5
O7—C17—C8	124.1 (4)	O27—C37—C28	125.7 (3)
O7—C17—H17	118.0	O27—C37—H37	117.1
C8—C17—H17	118.0	C28—C37—H37	117.1
O5—C18—O6	123.4 (4)	O25—C38—O26	123.9 (3)
O5—C18—C19	126.1 (4)	O25—C38—C39	125.0 (3)
O6—C18—C19	110.5 (4)	O26—C38—C39	111.1 (3)
C18—C19—H19A	109.5	C38—C39—H39A	109.5
C18—C19—H19B	109.5	C38—C39—H39B	109.5
H19A—C19—H19B	109.5	H39A—C39—H39B	109.5
C18—C19—H19C	109.5	C38—C39—H39C	109.5
H19A—C19—H19C	109.5	H39A—C39—H39C	109.5
H19B—C19—H19C	109.5	H39B—C39—H39C	109.5
O3—C20—H20A	109.5	O23—C40—H40A	109.5
O3—C20—H20B	109.5	O23—C40—H40B	109.5
H20A—C20—H20B	109.5	H40A—C40—H40B	109.5
O3—C20—H20C	109.5	O23—C40—H40C	109.5
H20A—C20—H20C	109.5	H40A—C40—H40C	109.5
H20B—C20—H20C	109.5	H40B—C40—H40C	109.5
C15—C1—C2—C3	171.5 (3)	C35—C21—C22—C23	−68.7 (3)
C14—C1—C2—C3	−70.9 (4)	C34—C21—C22—C23	174.2 (3)
C13A—C1—C2—C3	54.7 (5)	C33A—C21—C22—C23	57.1 (3)
C5—O2—C3A—C3	−178.8 (3)	C25—O22—C23A—C23	−171.8 (3)
C5—O2—C3A—C10B	−50.9 (4)	C25—O22—C23A—C30B	−46.1 (3)
O2—C3A—C3—C2	−178.3 (3)	O22—C23A—C23—C22	−179.9 (3)
C10B—C3A—C3—C2	56.5 (4)	C30B—C23A—C23—C22	56.8 (4)
C1—C2—C3—C3A	−62.1 (5)	C21—C22—C23—C23A	−64.5 (4)
C3A—O2—C5—O1	−164.9 (3)	C23A—O22—C25—O21	−172.6 (3)
C3A—O2—C5—C5A	19.4 (5)	C23A—O22—C25—C25A	9.0 (4)
O1—C5—C5A—C6	−4.2 (5)	O21—C25—C25A—C26	−2.8 (5)
O2—C5—C5A—C6	171.3 (3)	O22—C25—C25A—C26	175.5 (3)
O1—C5—C5A—C10A	−177.9 (3)	O21—C25—C25A—C30A	−173.1 (3)
O2—C5—C5A—C10A	−2.4 (5)	O22—C25—C25A—C30A	5.2 (5)
C5—C5A—C6—O8	2.4 (5)	C25—C25A—C26—O28	0.3 (5)
C10A—C5A—C6—O8	176.2 (3)	C30A—C25A—C26—O28	170.7 (3)
C5—C5A—C6—C7	−171.4 (3)	C25—C25A—C26—C27	−177.4 (3)
C10A—C5A—C6—C7	2.4 (4)	C30A—C25A—C26—C27	−7.0 (4)
O8—C6—C7—C8	140.2 (3)	O28—C26—C27—C28	139.1 (3)
C5A—C6—C7—C8	−45.4 (4)	C25A—C26—C27—C28	−42.9 (4)
O8—C6—C7—C16	−39.8 (4)	O28—C26—C27—C36	−38.5 (4)
C5A—C6—C7—C16	134.6 (3)	C25A—C26—C27—C36	139.5 (3)
C6—C7—C8—C17	173.0 (3)	C26—C27—C28—C37	−177.5 (3)
C16—C7—C8—C17	−6.9 (5)	C36—C27—C28—C37	−0.2 (5)
C6—C7—C8—C9	−9.2 (4)	C26—C27—C28—C29	−2.6 (4)
C16—C7—C8—C9	170.9 (3)	C36—C27—C28—C29	174.7 (3)
C7—C8—C9—C10	74.3 (4)	C27—C28—C29—C30	73.0 (4)
C17—C8—C9—C10	−107.8 (3)	C37—C28—C29—C30	−112.0 (3)
C18—O6—C10—C9	−79.0 (3)	C38—O26—C30—C29	−80.8 (3)
C18—O6—C10—C10A	159.7 (3)	C38—O26—C30—C30A	157.8 (2)
C8—C9—C10—O6	−154.7 (3)	C28—C29—C30—O26	−165.0 (2)
C8—C9—C10—C10A	−35.1 (4)	C28—C29—C30—C30A	−44.3 (3)
C6—C5A—C10A—C10	70.7 (4)	C26—C25A—C30A—C30	73.1 (3)
C5—C5A—C10A—C10	−115.7 (3)	C25—C25A—C30A—C30	−117.0 (3)
C6—C5A—C10A—C10B	−157.0 (3)	C26—C25A—C30A—C30B	−152.1 (3)
C5—C5A—C10A—C10B	16.6 (4)	C25—C25A—C30A—C30B	17.8 (4)
O6—C10—C10A—C5A	72.0 (3)	O26—C30—C30A—C25A	80.4 (3)
C9—C10—C10A—C5A	−47.8 (3)	C29—C30—C30A—C25A	−38.3 (3)
O6—C10—C10A—C10B	−56.7 (3)	O26—C30—C30A—C30B	−49.2 (3)
C9—C10—C10A—C10B	−176.5 (2)	C29—C30—C30A—C30B	−167.9 (2)
O2—C3A—C10B—C11	−55.5 (4)	O22—C23A—C30B—C31	−50.9 (3)
C3—C3A—C10B—C11	68.4 (4)	C23—C23A—C30B—C31	70.5 (3)
O2—C3A—C10B—C13A	−169.9 (2)	O22—C23A—C30B—C33A	−165.9 (2)
C3—C3A—C10B—C13A	−46.0 (4)	C23—C23A—C30B—C33A	−44.4 (3)
O2—C3A—C10B—C10A	63.1 (3)	O22—C23A—C30B—C30A	67.3 (3)
C3—C3A—C10B—C10A	−173.0 (3)	C23—C23A—C30B—C30A	−171.3 (2)
C5A—C10A—C10B—C3A	−44.9 (3)	C25A—C30A—C30B—C23A	−50.8 (3)
C10—C10A—C10B—C3A	85.1 (3)	C30—C30A—C30B—C23A	81.3 (3)
C5A—C10A—C10B—C11	79.2 (3)	C25A—C30A—C30B—C31	72.0 (3)
C10—C10A—C10B—C11	−150.7 (3)	C30—C30A—C30B—C31	−155.9 (2)
C5A—C10A—C10B—C13A	−171.3 (2)	C25A—C30A—C30B—C33A	−177.2 (2)
C10—C10A—C10B—C13A	−41.2 (3)	C30—C30A—C30B—C33A	−45.0 (3)
C13—O4—C11—C10B	15.9 (3)	C33—O24—C31—C30B	7.1 (3)
C3A—C10B—C11—O4	−155.2 (3)	C23A—C30B—C31—O24	−149.6 (2)
C13A—C10B—C11—O4	−33.9 (3)	C33A—C30B—C31—O24	−27.4 (3)
C10A—C10B—C11—O4	84.9 (3)	C30A—C30B—C31—O24	92.6 (2)
C3A—C10B—C13A—C13	161.7 (3)	C23A—C30B—C33A—C33	159.2 (2)
C11—C10B—C13A—C13	38.7 (3)	C31—C30B—C33A—C33	36.4 (3)
C10A—C10B—C13A—C13	−74.3 (3)	C30A—C30B—C33A—C33	−78.2 (3)
C3A—C10B—C13A—C1	38.2 (4)	C23A—C30B—C33A—C21	37.2 (3)
C11—C10B—C13A—C1	−84.8 (3)	C31—C30B—C33A—C21	−85.5 (3)
C10A—C10B—C13A—C1	162.2 (3)	C30A—C30B—C33A—C21	159.9 (2)
C2—C1—C13A—C13	−159.6 (3)	C35—C21—C33A—C33	−36.2 (4)
C15—C1—C13A—C13	82.1 (4)	C22—C21—C33A—C33	−159.0 (3)
C14—C1—C13A—C13	−38.0 (5)	C34—C21—C33A—C33	82.8 (3)
C2—C1—C13A—C10B	−42.3 (4)	C35—C21—C33A—C30B	80.1 (3)
C15—C1—C13A—C10B	−160.7 (3)	C22—C21—C33A—C30B	−42.7 (3)
C14—C1—C13A—C10B	79.2 (4)	C34—C21—C33A—C30B	−160.8 (3)
C11—O4—C13—O3	−109.2 (3)	C31—O24—C33—O23	−100.7 (3)
C11—O4—C13—C13A	9.8 (3)	C31—O24—C33—C33A	17.3 (3)
C20—O3—C13—O4	−66.5 (4)	C40—O23—C33—O24	−55.5 (3)
C20—O3—C13—C13A	175.6 (3)	C40—O23—C33—C33A	−172.2 (3)
C10B—C13A—C13—O4	−31.0 (3)	C30B—C33A—C33—O24	−33.9 (3)
C1—C13A—C13—O4	94.8 (3)	C21—C33A—C33—O24	90.9 (3)
C10B—C13A—C13—O3	89.8 (3)	C30B—C33A—C33—O23	86.5 (2)
C1—C13A—C13—O3	−144.4 (3)	C21—C33A—C33—O23	−148.7 (2)
C7—C8—C17—O7	179.1 (4)	C27—C28—C37—O27	165.4 (4)
C9—C8—C17—O7	1.2 (6)	C29—C28—C37—O27	−9.8 (5)
C10—O6—C18—O5	3.2 (6)	C30—O26—C38—O25	0.1 (4)
C10—O6—C18—C19	−178.6 (3)	C30—O26—C38—C39	−179.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8O···O1	0.82	1.78	2.495 (4)	146
O28—H28O···O21	0.82	1.80	2.526 (3)	146
O28—H28O···O23^i	0.82	2.56	3.125 (3)	127

Symmetry code: (i) −x+1, y+1/2, −z+1.