(1R,4S,8R,12S,13S,14R,16S,19R)-14-Hydr­oxy-7,7-dimethyl-17-methyl­ene-2,9,18-trioxo-3,10-dioxapenta­cyclo­[14.2.1.0^1,13.0^4,12.0^8,12]nona­dec-19-yl acetate

The title compound, C₂₂H₂₆O₈, prepared from the natural diterpenoid Macrocalyxin J, is built up from five fused rings. Cyclohenane ring A adopts a chair conformation, ring B exists in a screw-boat conformation and ring C adopts a boat conformation; the two five membered rings adopt envelope conformations. Two unique mol­ecules are present in the asymmetric unit; both independent mol­ecules have the same absolute configuration, the absolute configuration being deduced from the chirality of Macrocalyxin A, which was isolated from the same plant (i.e. Rabdosia macrocalyx) as Macrocalyxin J. The crystal structure displays intermolecular O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.051
• wR factor = 0.115
• Data-to-parameter ratio = 8.5

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:      0.744     1.000
            Tmin(prime) and Tmax expected:      0.949     0.968
            RR(prime) =      0.758
            Please check that your absorption correction is appropriate.
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.130
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.76
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.97 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.22 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C47
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.968
            Tmax scaled      0.968 Tmin scaled      0.720
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           27.00
           From the CIF: _reflns_number_total               4945
           Count of symmetry unique reflns         4959
           Completeness (_total/calc)             99.72%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C19    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C25    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C28    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C36    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C37    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C38    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C40    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C43    = .          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          5

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

  18 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   9 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

---

S1. Comment

Since the natural diterpenoid Macrocalyxin J exhibits cytotoxicity in vitro against cultures of Hela cells and the IC₅₀ =31.597µg/ml (Shi et al., 2007), we have derived the title compound from it.

The crystal packing is shown in Fig. 3. Two unique molecules are present in the asymmetric unit, both molecule 1 (Fig.1) and molecule 2 (Fig.2) are built up from five fused rings, three six membered and two five membered rings. Some geometrical features of these rings were investigated using PLATON (Spek, 2003).

For the molecule 1, cyclohexane ring A (C4—C8/C12) adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) Q = 0.5295 (42) Å, and θ= 157.69 (43) and φ = 271.5 (11) °, ring B (O3/C2/C1/C13/C12/C4) exists in a screw-boat conformation (Q = 0.6672 (33) Å, θ = 108.66 (28) and φ = 92.0 (3) °), ring C (C1/C13—C16/C19) adopt the boat conformation (Q = 0.8109 (35) Å, θ = 79.21 (24) and φ = 294.2 (2) °). The two five-membered rings, ring D (C1/C18/C17/C16/C19) adopts an envelope conformation with puckering parameters Q2 = 0.4565 (34) Å, and φ2 = 143.6 (4)° (envelope on C19), the ring E (O10/C9/C8/C12/C11) adopts an envelope conformation with puckering parameters Q2 = 0.3341 (36) Å, and φ2 = 284.7 (6)° (envelope on C12).

For the molecule 2, cyclohexane ring A' (C28—C32/C36) adopts a chair conformation with puckering parameters Q = 0.5312 (40) Å, and θ= 156.14 (41) and φ =274.4 (10) °, ring B' (O27/C26/C25/C37/C36/C28) exists in a screw-boat conformation (Q = 0.6421 (36) Å, and θ= 110.70 (31) and φ =94.7 (3) °), ring C' (C25/C37—C40/C43) adopt the boat conformation (Q = 0.8400 (37) Å, θ = 80.52 (25) and φ = 293.6 (3)°). The two five-membered rings, ring D' (C25/C42/C41/C40/C43) adopts an envelope conformation with puckering parameters Q2 = 0.4526 (38) Å, and φ2 = 146.0 (5)° (envelope on C43), the ring E' (O34/C33/C32/C36/C35) adopts an envelope conformation with puckering parameters Q2 = 0.3156 (35) Å, and φ2 = 284.8 (6) ° (envelope on C36).

Since the title compound was prepared from Macrocalyxin J, which was isolated from the same plant (i.e. Rabdosia macrocalyx) as Macrocalyxin A, the configuration can be deduced from the known chirality of the Macrocalyxin A (Shi et al., 2003),and thus Fig. 1 and Fig. 2 represents the correct absolute configuration.

Related literature

For related literature, see: Cremer & Pople (1975); Shi et al. (2003, 2007); Wang et al. (1984).

S2. Experimental

Cooling in ice-water bath, 0.2 ml Jones reagent was added to a solution of Macrocalyxin J (200 mg; isolated from Rabdosia macrocalyx) in acetone (8 ml), after stirring for 20 minutes, filtrated and the solution was added 120 ml 15% NaHCO₃ in water, the mixture extracted 3 times with 90 ml diethyl ether, after evaporation of the solvent, a white residue was gained. Recrystallization with methanol gave the title compound as colorless crystals.

Crystals suitable for X-ray structure analysis were obtained by slow evaporation from a solution of methanol at room temperature.

S3. Refinement

H atoms bonded to O atoms and some H atoms bonded to CH were located in a difference map, and with Uĩso~(H) = 1.2U~eq~(O, C). Other H atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.96 Å (CH₃), 0.97 Å (CH₂) and 0.98(CH) and with the temperature factors U_iso= 1.5 U_eq(CH₃) and 1.2 U_eq(CH₂, CH). Both independent molecules have the same absolute configuration, although this could not be determined reliably from the X-ray data and Friedel reflections were merged.

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 1997) and PLATON (Spek, 2003).

Figures

	Fig. 1. Perspective view of molecule 1 of the title compound, shown with 30% probability displacement ellipsoids.
	Fig. 2. Perspective view of molecule 2 of the title compound, shown with 30% probability displacement ellipsoids.
	Fig. 3. The crystal packing diagram for the title compound viewed normal to the (100) plane. H atoms have been omitted for clarity.

(1R,4S,8R,12S,13S,14R,16S, 19R)-14-Hydroxy-7,7-dimethyl-17-methylene-2,9,18-trioxo-3,10- dioxapentacyclo[14.2.1.0^1,13.0^4,12.0^8,12]nonadec-19-yl acetate

Crystal data

C22H26O8	F(000) = 1776
Mr = 418.43	Dx = 1.362 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5228 reflections
a = 12.0055 (11) Å	θ = 4.7–43.5°
b = 13.5835 (13) Å	µ = 0.10 mm^−1
c = 25.027 (2) Å	T = 293 K
V = 4081.3 (6) Å^3	Prismatic, colorless
Z = 8	0.49 × 0.43 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4945 independent reflections
Radiation source: fine-focus sealed tube	3810 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.130
φ and ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −13→15
Tmin = 0.744, Tmax = 1.000	k = −16→17
24111 measured reflections	l = −31→30

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0476P)^2] where P = (Fo^2 + 2Fc^2)/3
4945 reflections	(Δ/σ)max < 0.001
583 parameters	Δρmax = 0.17 e Å^−3
5 restraints	Δρmin = −0.18 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	−0.0773 (2)	0.39858 (19)	0.15867 (9)	0.0571 (7)
O2	0.0191 (3)	−0.0582 (2)	0.03545 (10)	0.0745 (9)
O3	0.0225 (2)	0.27304 (16)	0.18225 (8)	0.0443 (5)
O4	0.2759 (2)	0.22386 (19)	0.08037 (10)	0.0505 (6)
O5	−0.1365 (2)	0.36138 (18)	0.04604 (10)	0.0557 (6)
O6	0.1069 (2)	0.50275 (16)	0.10433 (8)	0.0479 (6)
O7	0.1822 (3)	0.4751 (2)	0.18441 (10)	0.0726 (8)
O10	−0.0833 (2)	0.05219 (18)	0.07849 (10)	0.0533 (6)
O25	0.4868 (2)	0.8092 (2)	0.15326 (11)	0.0702 (8)
O26	0.4933 (2)	0.31505 (19)	0.05534 (9)	0.0564 (7)
O27	0.5162 (2)	0.66457 (19)	0.18918 (9)	0.0559 (7)
O28	0.7958 (2)	0.5540 (2)	0.12833 (11)	0.0574 (7)
O29	0.4717 (2)	0.7662 (2)	0.03890 (11)	0.0700 (8)
O30	0.7150 (2)	0.85219 (17)	0.12142 (9)	0.0535 (6)
O31	0.7390 (3)	0.8188 (3)	0.20754 (12)	0.0931 (11)
O34	0.41033 (18)	0.45354 (18)	0.07968 (8)	0.0470 (6)
C1	0.0423 (3)	0.3345 (2)	0.09064 (11)	0.0359 (7)
C2	−0.0100 (3)	0.3384 (2)	0.14598 (12)	0.0395 (7)
C4	0.1025 (3)	0.1989 (2)	0.16628 (12)	0.0412 (8)
H4	0.1748	0.2301	0.1596	0.049*
C5	0.1133 (4)	0.1263 (3)	0.21173 (13)	0.0585 (10)
H5A	0.0404	0.1013	0.2216	0.070*
H5B	0.1458	0.1583	0.2427	0.070*
C6	0.1873 (4)	0.0425 (3)	0.19322 (16)	0.0671 (11)
H6A	0.2034	0.0002	0.2235	0.081*
H6B	0.2573	0.0695	0.1806	0.081*
C7	0.1356 (3)	−0.0193 (3)	0.14880 (15)	0.0572 (10)
C8	0.1063 (3)	0.0509 (2)	0.10027 (13)	0.0432 (8)
C9	0.0142 (3)	0.0071 (3)	0.06754 (13)	0.0507 (9)
C11	−0.0653 (3)	0.1293 (2)	0.11657 (12)	0.0428 (8)
H11A	−0.0862	0.1076	0.1521	0.051*
H11B	−0.1092	0.1868	0.1074	0.051*
C12	0.0589 (2)	0.1534 (2)	0.11442 (11)	0.0345 (7)
C13	0.0763 (3)	0.2297 (2)	0.06897 (11)	0.0336 (6)
H13	0.0215	0.2132	0.0414	0.040*
C14	0.1898 (3)	0.2287 (2)	0.04108 (12)	0.0413 (7)
H14	0.1941	0.1690	0.0192	0.050*
C15	0.2046 (3)	0.3179 (2)	0.00380 (12)	0.0448 (8)
H15A	0.1711	0.3027	−0.0305	0.054*
H15B	0.2836	0.3285	−0.0020	0.054*
C16	0.1526 (3)	0.4140 (2)	0.02532 (12)	0.0426 (8)
H16	0.1971	0.4716	0.0152	0.051*
C17	0.0344 (3)	0.4247 (2)	0.00754 (12)	0.0481 (9)
C18	−0.0376 (3)	0.3743 (2)	0.04759 (12)	0.0415 (8)
C19	0.1400 (3)	0.4067 (2)	0.08557 (12)	0.0411 (8)
C20	−0.0059 (4)	0.4687 (3)	−0.03553 (14)	0.0744 (13)
H20A	−0.0823	0.4690	−0.0418	0.089*
H20B	0.0421	0.4992	−0.0595	0.089*
C21	0.2210 (4)	−0.0943 (3)	0.12855 (19)	0.0821 (14)
H21A	0.2889	−0.0610	0.1195	0.123*
H21B	0.1921	−0.1270	0.0975	0.123*
H21C	0.2355	−0.1420	0.1560	0.123*
C22	0.0342 (4)	−0.0769 (3)	0.16967 (17)	0.0720 (12)
H22A	0.0558	−0.1156	0.2000	0.108*
H22B	0.0067	−0.1195	0.1420	0.108*
H22C	−0.0232	−0.0315	0.1800	0.108*
C23	0.1326 (3)	0.5276 (3)	0.15509 (14)	0.0525 (9)
C24	0.0901 (5)	0.6276 (3)	0.16802 (16)	0.0821 (15)
H24A	0.1184	0.6478	0.2022	0.123*
H24B	0.0102	0.6264	0.1691	0.123*
H24C	0.1143	0.6732	0.1411	0.123*
C25	0.6069 (3)	0.7044 (2)	0.10372 (12)	0.0377 (7)
C26	0.5321 (3)	0.7303 (3)	0.14997 (14)	0.0497 (9)
C28	0.5763 (3)	0.5727 (3)	0.18558 (12)	0.0458 (8)
C29	0.5426 (3)	0.5069 (3)	0.23096 (12)	0.0622 (11)
H29A	0.4624	0.4978	0.2309	0.075*
H29B	0.5637	0.5365	0.2647	0.075*
C30	0.6000 (4)	0.4088 (3)	0.22445 (13)	0.0653 (11)
H30A	0.5882	0.3698	0.2564	0.078*
H30B	0.6795	0.4196	0.2207	0.078*
C31	0.5579 (3)	0.3511 (3)	0.17602 (13)	0.0532 (9)
C32	0.5758 (3)	0.4175 (2)	0.12488 (12)	0.0396 (7)
C33	0.4935 (3)	0.3876 (2)	0.08301 (12)	0.0420 (8)
C35	0.4291 (3)	0.5328 (3)	0.11635 (12)	0.0438 (8)
H35A	0.3837	0.5247	0.1481	0.053*
H35B	0.4109	0.5954	0.0999	0.053*
C36	0.5532 (2)	0.5285 (2)	0.13060 (11)	0.0361 (7)
C37	0.6168 (3)	0.5915 (2)	0.08923 (11)	0.0345 (7)
H37	0.5773	0.5829	0.0553	0.041*
C38	0.7378 (3)	0.5607 (3)	0.07876 (13)	0.0439 (8)
C39	0.7965 (3)	0.6321 (2)	0.04099 (14)	0.0517 (9)
H39A	0.7759	0.6163	0.0045	0.062*
H39B	0.8763	0.6232	0.0443	0.062*
C40	0.7676 (3)	0.7411 (3)	0.05215 (14)	0.0485 (9)
C41	0.6689 (3)	0.7737 (3)	0.02033 (13)	0.0539 (9)
C42	0.5664 (3)	0.7532 (3)	0.05151 (13)	0.0488 (9)
C43	0.7246 (3)	0.7493 (2)	0.10914 (13)	0.0413 (8)
C44	0.6660 (5)	0.8120 (3)	−0.02801 (16)	0.0833 (15)
H44A	0.5980	0.8272	−0.0438	0.100*
H44B	0.7320	0.8239	−0.0464	0.100*
C45	0.6298 (4)	0.2586 (3)	0.16936 (19)	0.0791 (13)
H45A	0.7057	0.2775	0.1630	0.119*
H45B	0.6030	0.2209	0.1396	0.119*
H45C	0.6258	0.2196	0.2013	0.119*
C46	0.4377 (4)	0.3195 (3)	0.18463 (14)	0.0650 (12)
H46A	0.4316	0.2851	0.2180	0.097*
H46B	0.4151	0.2769	0.1560	0.097*
H46C	0.3906	0.3766	0.1853	0.097*
C47	0.7231 (4)	0.8770 (3)	0.17307 (16)	0.0588 (10)
C48	0.7040 (4)	0.9838 (3)	0.18026 (18)	0.0796 (13)
H48A	0.6256	0.9972	0.1787	0.119*
H48B	0.7413	1.0194	0.1524	0.119*
H48C	0.7328	1.0040	0.2143	0.119*
H8	0.171 (3)	0.063 (2)	0.0796 (13)	0.049 (10)*
H19	0.2078 (18)	0.385 (2)	0.1015 (10)	0.031 (8)*
H28	0.6554 (17)	0.589 (2)	0.1872 (12)	0.045 (9)*
H32	0.653 (3)	0.402 (2)	0.1139 (13)	0.048 (9)*
H38	0.740 (3)	0.495 (3)	0.0650 (11)	0.037 (8)*
H40	0.830 (3)	0.783 (3)	0.0480 (13)	0.048 (10)*
H43	0.768 (3)	0.714 (3)	0.1363 (14)	0.055 (10)*
H4A	0.336 (3)	0.234 (4)	0.0637 (16)	0.096 (18)*
H28A	0.840 (3)	0.509 (3)	0.1307 (17)	0.084 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0640 (16)	0.0566 (15)	0.0508 (13)	0.0240 (14)	0.0136 (13)	0.0077 (12)
O2	0.110 (2)	0.0536 (16)	0.0604 (16)	0.0009 (16)	0.0056 (17)	−0.0162 (14)
O3	0.0565 (14)	0.0448 (13)	0.0315 (11)	0.0066 (11)	0.0022 (10)	0.0021 (10)
O4	0.0360 (13)	0.0637 (15)	0.0517 (13)	0.0011 (12)	0.0020 (12)	0.0048 (13)
O5	0.0457 (15)	0.0590 (16)	0.0624 (15)	0.0119 (12)	−0.0150 (13)	−0.0013 (12)
O6	0.0733 (17)	0.0365 (12)	0.0339 (11)	0.0004 (11)	−0.0012 (11)	−0.0007 (10)
O7	0.083 (2)	0.093 (2)	0.0417 (14)	0.0110 (18)	−0.0144 (14)	−0.0084 (15)
O10	0.0526 (15)	0.0511 (14)	0.0562 (14)	−0.0107 (12)	−0.0047 (12)	−0.0043 (12)
O25	0.0668 (18)	0.0666 (18)	0.0772 (18)	0.0206 (15)	0.0115 (15)	−0.0222 (15)
O26	0.0671 (17)	0.0567 (15)	0.0454 (13)	−0.0126 (13)	0.0045 (12)	−0.0114 (12)
O27	0.0620 (16)	0.0645 (16)	0.0412 (13)	−0.0083 (14)	0.0183 (12)	−0.0139 (12)
O28	0.0497 (15)	0.0595 (17)	0.0629 (15)	0.0171 (13)	−0.0058 (13)	0.0107 (13)
O29	0.0652 (18)	0.0711 (18)	0.0738 (18)	0.0248 (15)	−0.0267 (15)	0.0011 (15)
O30	0.0673 (17)	0.0458 (14)	0.0473 (14)	−0.0076 (12)	0.0056 (13)	−0.0067 (11)
O31	0.135 (3)	0.092 (2)	0.0515 (16)	−0.015 (2)	−0.0051 (19)	−0.0069 (17)
O34	0.0410 (13)	0.0589 (14)	0.0412 (12)	−0.0056 (12)	−0.0066 (11)	−0.0046 (11)
C1	0.0360 (17)	0.0395 (17)	0.0321 (15)	0.0055 (13)	−0.0008 (13)	0.0000 (13)
C2	0.0398 (18)	0.0377 (17)	0.0409 (17)	0.0007 (15)	0.0008 (15)	0.0005 (14)
C4	0.0382 (18)	0.0461 (19)	0.0392 (16)	0.0067 (14)	−0.0008 (14)	0.0015 (14)
C5	0.077 (3)	0.057 (2)	0.0414 (18)	0.008 (2)	−0.0172 (19)	0.0046 (17)
C6	0.070 (3)	0.063 (3)	0.067 (2)	0.018 (2)	−0.018 (2)	0.018 (2)
C7	0.067 (2)	0.047 (2)	0.058 (2)	0.0143 (18)	−0.0004 (19)	0.0117 (18)
C8	0.047 (2)	0.0361 (17)	0.0466 (18)	0.0042 (15)	0.0088 (16)	0.0007 (15)
C9	0.070 (3)	0.0391 (18)	0.0431 (18)	0.0007 (18)	0.0051 (18)	0.0033 (16)
C11	0.0416 (19)	0.0459 (18)	0.0411 (17)	−0.0027 (15)	0.0021 (15)	0.0022 (15)
C12	0.0320 (16)	0.0368 (16)	0.0348 (15)	0.0039 (13)	0.0011 (13)	0.0035 (13)
C13	0.0340 (16)	0.0345 (15)	0.0324 (15)	−0.0001 (13)	−0.0031 (13)	0.0000 (13)
C14	0.0416 (18)	0.0423 (18)	0.0401 (17)	−0.0008 (15)	0.0018 (14)	−0.0026 (14)
C15	0.048 (2)	0.0512 (19)	0.0353 (16)	−0.0026 (16)	0.0084 (15)	0.0010 (15)
C16	0.056 (2)	0.0376 (18)	0.0343 (16)	−0.0083 (16)	0.0053 (15)	0.0036 (14)
C17	0.068 (2)	0.0427 (19)	0.0341 (16)	0.0077 (17)	−0.0025 (16)	0.0008 (15)
C18	0.048 (2)	0.0390 (18)	0.0374 (17)	0.0097 (15)	−0.0080 (16)	−0.0044 (14)
C19	0.046 (2)	0.0443 (19)	0.0328 (16)	−0.0012 (16)	−0.0011 (15)	−0.0008 (15)
C20	0.100 (4)	0.081 (3)	0.042 (2)	0.018 (3)	−0.005 (2)	0.012 (2)
C21	0.091 (3)	0.062 (3)	0.093 (3)	0.035 (3)	0.001 (3)	0.015 (2)
C22	0.095 (3)	0.052 (2)	0.069 (2)	0.006 (2)	0.011 (2)	0.021 (2)
C23	0.061 (2)	0.058 (2)	0.0383 (18)	−0.0153 (19)	0.0054 (18)	−0.0045 (18)
C24	0.136 (5)	0.057 (3)	0.053 (2)	−0.005 (3)	0.021 (3)	−0.015 (2)
C25	0.0400 (18)	0.0402 (17)	0.0328 (15)	0.0067 (14)	0.0001 (13)	−0.0017 (13)
C26	0.0374 (18)	0.062 (2)	0.050 (2)	−0.0009 (17)	0.0043 (16)	−0.0174 (19)
C28	0.042 (2)	0.059 (2)	0.0361 (17)	−0.0106 (17)	0.0028 (15)	−0.0047 (15)
C29	0.070 (3)	0.089 (3)	0.0279 (16)	−0.030 (2)	0.0043 (16)	−0.0071 (18)
C30	0.077 (3)	0.082 (3)	0.0372 (19)	−0.020 (2)	−0.0132 (19)	0.0215 (19)
C31	0.057 (2)	0.061 (2)	0.0416 (18)	−0.0136 (18)	−0.0032 (17)	0.0192 (17)
C32	0.0357 (18)	0.0476 (19)	0.0355 (16)	−0.0014 (15)	0.0037 (14)	0.0045 (14)
C33	0.047 (2)	0.0493 (19)	0.0299 (15)	−0.0111 (17)	0.0080 (15)	0.0020 (15)
C35	0.0357 (17)	0.056 (2)	0.0396 (16)	−0.0025 (16)	0.0030 (14)	−0.0084 (15)
C36	0.0341 (17)	0.0466 (19)	0.0275 (14)	−0.0026 (14)	0.0019 (13)	−0.0008 (13)
C37	0.0396 (17)	0.0356 (16)	0.0283 (14)	0.0022 (13)	0.0016 (13)	0.0023 (13)
C38	0.0423 (19)	0.0420 (19)	0.0475 (19)	0.0059 (15)	0.0089 (16)	0.0034 (16)
C39	0.050 (2)	0.047 (2)	0.058 (2)	0.0120 (17)	0.0213 (18)	0.0034 (17)
C40	0.050 (2)	0.045 (2)	0.051 (2)	−0.0025 (17)	0.0159 (17)	0.0020 (16)
C41	0.080 (3)	0.0402 (19)	0.0413 (19)	0.0109 (19)	0.0048 (18)	0.0008 (15)
C42	0.061 (2)	0.0403 (19)	0.0456 (18)	0.0118 (17)	−0.0118 (18)	0.0004 (15)
C43	0.0422 (19)	0.0413 (19)	0.0403 (17)	0.0033 (15)	0.0008 (15)	0.0009 (15)
C44	0.121 (4)	0.073 (3)	0.056 (2)	0.013 (3)	0.010 (3)	0.021 (2)
C45	0.086 (3)	0.068 (3)	0.083 (3)	0.002 (2)	−0.011 (3)	0.030 (2)
C46	0.070 (3)	0.079 (3)	0.045 (2)	−0.027 (2)	0.0018 (19)	0.0154 (19)
C47	0.061 (2)	0.059 (2)	0.056 (2)	−0.019 (2)	0.008 (2)	−0.014 (2)
C48	0.086 (3)	0.070 (3)	0.082 (3)	−0.023 (2)	0.024 (3)	−0.026 (2)

Geometric parameters (Å, º)

O1—C2	1.193 (4)	C20—H20A	0.9300
O2—C9	1.199 (4)	C20—H20B	0.9300
O3—C2	1.328 (4)	C21—H21A	0.9600
O3—C4	1.447 (4)	C21—H21B	0.9600
O4—C14	1.428 (4)	C21—H21C	0.9600
O4—H4A	0.84 (2)	C22—H22A	0.9600
O5—C18	1.201 (4)	C22—H22B	0.9600
O6—C23	1.350 (4)	C22—H22C	0.9600
O6—C19	1.442 (4)	C23—C24	1.487 (6)
O7—C23	1.184 (4)	C24—H24A	0.9600
O10—C9	1.348 (5)	C24—H24B	0.9600
O10—C11	1.432 (4)	C24—H24C	0.9600
O25—C26	1.204 (4)	C25—C26	1.507 (5)
O26—C33	1.205 (4)	C25—C42	1.544 (4)
O27—C26	1.340 (4)	C25—C43	1.544 (5)
O27—C28	1.444 (5)	C25—C37	1.581 (4)
O28—C38	1.426 (4)	C28—C29	1.501 (5)
O28—H28A	0.81 (2)	C28—C36	1.526 (4)
O29—C42	1.193 (4)	C28—H28	0.976 (18)
O30—C47	1.339 (4)	C29—C30	1.509 (6)
O30—C43	1.436 (4)	C29—H29A	0.9700
O31—C47	1.185 (5)	C29—H29B	0.9700
O34—C33	1.344 (4)	C30—C31	1.529 (5)
O34—C35	1.433 (4)	C30—H30A	0.9700
C1—C2	1.521 (4)	C30—H30B	0.9700
C1—C19	1.534 (5)	C31—C46	1.521 (6)
C1—C18	1.540 (4)	C31—C45	1.534 (6)
C1—C13	1.578 (4)	C31—C32	1.580 (4)
C4—C5	1.511 (5)	C32—C33	1.495 (5)
C4—C12	1.530 (4)	C32—C36	1.540 (5)
C4—H4	0.9800	C32—H32	0.99 (4)
C5—C6	1.517 (6)	C35—C36	1.533 (4)
C5—H5A	0.9700	C35—H35A	0.9700
C5—H5B	0.9700	C35—H35B	0.9700
C6—C7	1.525 (6)	C36—C37	1.544 (4)
C6—H6A	0.9700	C37—C38	1.534 (5)
C6—H6B	0.9700	C37—H37	0.9800
C7—C21	1.532 (6)	C38—C39	1.526 (5)
C7—C22	1.538 (6)	C38—H38	0.95 (3)
C7—C8	1.584 (5)	C39—C40	1.546 (5)
C8—C9	1.499 (5)	C39—H39A	0.9700
C8—C12	1.546 (4)	C39—H39B	0.9700
C8—H8	0.95 (4)	C40—C41	1.494 (5)
C11—C12	1.527 (4)	C40—C43	1.521 (5)
C11—H11A	0.9700	C40—H40	0.95 (4)
C11—H11B	0.9700	C41—C44	1.317 (5)
C12—C13	1.553 (4)	C41—C42	1.484 (5)
C13—C14	1.532 (4)	C43—H43	0.98 (4)
C13—H13	0.9800	C44—H44A	0.9300
C14—C15	1.539 (4)	C44—H44B	0.9300
C14—H14	0.9800	C45—H45A	0.9600
C15—C16	1.544 (5)	C45—H45B	0.9600
C15—H15A	0.9700	C45—H45C	0.9600
C15—H15B	0.9700	C46—H46A	0.9600
C16—C17	1.495 (5)	C46—H46B	0.9600
C16—C19	1.519 (4)	C46—H46C	0.9600
C16—H16	0.9800	C47—C48	1.480 (6)
C17—C20	1.324 (5)	C48—H48A	0.9600
C17—C18	1.490 (5)	C48—H48B	0.9600
C19—H19	0.952 (18)	C48—H48C	0.9600
C2—O3—C4	118.1 (2)	H24A—C24—H24B	109.5
C14—O4—H4A	105 (3)	C23—C24—H24C	109.5
C23—O6—C19	118.0 (3)	H24A—C24—H24C	109.5
C9—O10—C11	109.6 (3)	H24B—C24—H24C	109.5
C26—O27—C28	117.3 (2)	C26—C25—C42	111.2 (3)
C38—O28—H28A	116 (3)	C26—C25—C43	112.7 (3)
C47—O30—C43	116.4 (3)	C42—C25—C43	101.1 (3)
C33—O34—C35	110.1 (2)	C26—C25—C37	116.6 (3)
C2—C1—C19	111.6 (2)	C42—C25—C37	104.2 (2)
C2—C1—C18	111.6 (3)	C43—C25—C37	109.6 (3)
C19—C1—C18	101.1 (3)	O25—C26—O27	118.6 (3)
C2—C1—C13	116.8 (2)	O25—C26—C25	122.0 (4)
C19—C1—C13	110.5 (2)	O27—C26—C25	119.4 (3)
C18—C1—C13	103.8 (2)	O27—C28—C29	109.4 (3)
O1—C2—O3	118.4 (3)	O27—C28—C36	107.8 (3)
O1—C2—C1	123.1 (3)	C29—C28—C36	113.5 (3)
O3—C2—C1	118.5 (3)	O27—C28—H28	107 (2)
O3—C4—C5	107.6 (3)	C29—C28—H28	111.5 (19)
O3—C4—C12	106.8 (2)	C36—C28—H28	107.6 (19)
C5—C4—C12	113.8 (3)	C28—C29—C30	108.7 (3)
O3—C4—H4	109.5	C28—C29—H29A	109.9
C5—C4—H4	109.5	C30—C29—H29A	109.9
C12—C4—H4	109.5	C28—C29—H29B	109.9
C4—C5—C6	108.1 (3)	C30—C29—H29B	109.9
C4—C5—H5A	110.1	H29A—C29—H29B	108.3
C6—C5—H5A	110.1	C29—C30—C31	112.8 (3)
C4—C5—H5B	110.1	C29—C30—H30A	109.0
C6—C5—H5B	110.1	C31—C30—H30A	109.0
H5A—C5—H5B	108.4	C29—C30—H30B	109.0
C5—C6—C7	113.4 (3)	C31—C30—H30B	109.0
C5—C6—H6A	108.9	H30A—C30—H30B	107.8
C7—C6—H6A	108.9	C46—C31—C30	110.2 (3)
C5—C6—H6B	108.9	C46—C31—C45	108.6 (3)
C7—C6—H6B	108.9	C30—C31—C45	108.7 (3)
H6A—C6—H6B	107.7	C46—C31—C32	113.8 (3)
C6—C7—C21	109.6 (4)	C30—C31—C32	107.8 (3)
C6—C7—C22	110.8 (3)	C45—C31—C32	107.6 (3)
C21—C7—C22	107.7 (3)	C33—C32—C36	102.4 (3)
C6—C7—C8	108.5 (3)	C33—C32—C31	108.9 (3)
C21—C7—C8	107.2 (3)	C36—C32—C31	117.4 (3)
C22—C7—C8	113.0 (3)	C33—C32—H32	111 (2)
C9—C8—C12	102.2 (3)	C36—C32—H32	114 (2)
C9—C8—C7	110.1 (3)	C31—C32—H32	103.2 (19)
C12—C8—C7	116.6 (3)	O26—C33—O34	120.5 (3)
C9—C8—H8	112 (2)	O26—C33—C32	128.8 (3)
C12—C8—H8	106 (2)	O34—C33—C32	110.7 (3)
C7—C8—H8	110 (2)	O34—C35—C36	105.9 (3)
O2—C9—O10	121.0 (4)	O34—C35—H35A	110.6
O2—C9—C8	128.5 (4)	C36—C35—H35A	110.6
O10—C9—C8	110.5 (3)	O34—C35—H35B	110.6
O10—C11—C12	106.3 (3)	C36—C35—H35B	110.6
O10—C11—H11A	110.5	H35A—C35—H35B	108.7
C12—C11—H11A	110.5	C28—C36—C35	111.8 (3)
O10—C11—H11B	110.5	C28—C36—C32	115.9 (3)
C12—C11—H11B	110.5	C35—C36—C32	100.7 (3)
H11A—C11—H11B	108.7	C28—C36—C37	107.3 (3)
C11—C12—C4	113.0 (3)	C35—C36—C37	107.7 (2)
C11—C12—C8	100.0 (3)	C32—C36—C37	113.2 (2)
C4—C12—C8	115.7 (3)	C38—C37—C36	115.6 (2)
C11—C12—C13	107.5 (2)	C38—C37—C25	112.0 (3)
C4—C12—C13	107.8 (2)	C36—C37—C25	110.3 (2)
C8—C12—C13	112.6 (2)	C38—C37—H37	106.1
C14—C13—C12	116.6 (2)	C36—C37—H37	106.1
C14—C13—C1	113.2 (2)	C25—C37—H37	106.1
C12—C13—C1	108.4 (2)	O28—C38—C39	110.8 (3)
C14—C13—H13	105.9	O28—C38—C37	109.3 (3)
C12—C13—H13	105.9	C39—C38—C37	111.7 (3)
C1—C13—H13	105.9	O28—C38—H38	104.1 (18)
O4—C14—C13	109.3 (2)	C39—C38—H38	110.8 (18)
O4—C14—C15	111.8 (3)	C37—C38—H38	109.9 (19)
C13—C14—C15	111.9 (3)	C38—C39—C40	113.1 (3)
O4—C14—H14	107.9	C38—C39—H39A	109.0
C13—C14—H14	107.9	C40—C39—H39A	109.0
C15—C14—H14	107.9	C38—C39—H39B	109.0
C14—C15—C16	114.0 (2)	C40—C39—H39B	109.0
C14—C15—H15A	108.7	H39A—C39—H39B	107.8
C16—C15—H15A	108.7	C41—C40—C43	102.1 (3)
C14—C15—H15B	108.7	C41—C40—C39	111.5 (3)
C16—C15—H15B	108.7	C43—C40—C39	108.4 (3)
H15A—C15—H15B	107.6	C41—C40—H40	113 (2)
C17—C16—C19	101.9 (3)	C43—C40—H40	109 (2)
C17—C16—C15	111.2 (3)	C39—C40—H40	112 (2)
C19—C16—C15	109.3 (3)	C44—C41—C42	122.4 (4)
C17—C16—H16	111.3	C44—C41—C40	128.9 (4)
C19—C16—H16	111.3	C42—C41—C40	108.7 (3)
C15—C16—H16	111.3	O29—C42—C41	128.6 (3)
C20—C17—C18	122.9 (4)	O29—C42—C25	126.0 (4)
C20—C17—C16	129.3 (4)	C41—C42—C25	105.3 (3)
C18—C17—C16	107.8 (3)	O30—C43—C40	107.4 (3)
O5—C18—C17	128.2 (3)	O30—C43—C25	109.3 (3)
O5—C18—C1	125.9 (3)	C40—C43—C25	101.5 (3)
C17—C18—C1	105.7 (3)	O30—C43—H43	112 (2)
O6—C19—C16	106.9 (3)	C40—C43—H43	116 (2)
O6—C19—C1	109.9 (3)	C25—C43—H43	111 (2)
C16—C19—C1	101.6 (2)	C41—C44—H44A	120.0
O6—C19—H19	112.0 (18)	C41—C44—H44B	120.0
C16—C19—H19	110.5 (17)	H44A—C44—H44B	120.0
C1—C19—H19	115.1 (18)	C31—C45—H45A	109.5
C17—C20—H20A	120.0	C31—C45—H45B	109.5
C17—C20—H20B	120.0	H45A—C45—H45B	109.5
H20A—C20—H20B	120.0	C31—C45—H45C	109.5
C7—C21—H21A	109.5	H45A—C45—H45C	109.5
C7—C21—H21B	109.5	H45B—C45—H45C	109.5
H21A—C21—H21B	109.5	C31—C46—H46A	109.5
C7—C21—H21C	109.5	C31—C46—H46B	109.5
H21A—C21—H21C	109.5	H46A—C46—H46B	109.5
H21B—C21—H21C	109.5	C31—C46—H46C	109.5
C7—C22—H22A	109.5	H46A—C46—H46C	109.5
C7—C22—H22B	109.5	H46B—C46—H46C	109.5
H22A—C22—H22B	109.5	O31—C47—O30	123.1 (4)
C7—C22—H22C	109.5	O31—C47—C48	126.2 (4)
H22A—C22—H22C	109.5	O30—C47—C48	110.6 (4)
H22B—C22—H22C	109.5	C47—C48—H48A	109.5
O7—C23—O6	123.2 (4)	C47—C48—H48B	109.5
O7—C23—C24	126.0 (4)	H48A—C48—H48B	109.5
O6—C23—C24	110.8 (4)	C47—C48—H48C	109.5
C23—C24—H24A	109.5	H48A—C48—H48C	109.5
C23—C24—H24B	109.5	H48B—C48—H48C	109.5
C4—O3—C2—O1	178.7 (3)	C28—O27—C26—O25	−176.7 (3)
C4—O3—C2—C1	−2.7 (4)	C28—O27—C26—C25	2.3 (4)
C19—C1—C2—O1	82.7 (4)	C42—C25—C26—O25	−33.7 (4)
C18—C1—C2—O1	−29.7 (4)	C43—C25—C26—O25	79.1 (4)
C13—C1—C2—O1	−148.8 (3)	C37—C25—C26—O25	−153.0 (3)
C19—C1—C2—O3	−95.8 (3)	C42—C25—C26—O27	147.3 (3)
C18—C1—C2—O3	151.8 (3)	C43—C25—C26—O27	−100.0 (3)
C13—C1—C2—O3	32.7 (4)	C37—C25—C26—O27	28.0 (4)
C2—O3—C4—C5	−172.3 (3)	C26—O27—C28—C29	−176.6 (3)
C2—O3—C4—C12	−49.7 (4)	C26—O27—C28—C36	−52.7 (4)
O3—C4—C5—C6	174.1 (3)	O27—C28—C29—C30	176.1 (3)
C12—C4—C5—C6	55.9 (4)	C36—C28—C29—C30	55.7 (4)
C4—C5—C6—C7	−66.5 (4)	C28—C29—C30—C31	−67.8 (4)
C5—C6—C7—C21	173.7 (3)	C29—C30—C31—C46	−67.3 (4)
C5—C6—C7—C22	−67.6 (4)	C29—C30—C31—C45	173.8 (3)
C5—C6—C7—C8	57.0 (4)	C29—C30—C31—C32	57.5 (4)
C6—C7—C8—C9	−155.1 (3)	C46—C31—C32—C33	−32.0 (4)
C21—C7—C8—C9	86.7 (4)	C30—C31—C32—C33	−154.5 (3)
C22—C7—C8—C9	−31.8 (4)	C45—C31—C32—C33	88.4 (4)
C6—C7—C8—C12	−39.3 (4)	C46—C31—C32—C36	83.7 (4)
C21—C7—C8—C12	−157.5 (3)	C30—C31—C32—C36	−38.9 (4)
C22—C7—C8—C12	84.0 (4)	C45—C31—C32—C36	−155.9 (3)
C11—O10—C9—O2	−178.0 (3)	C35—O34—C33—O26	179.9 (3)
C11—O10—C9—C8	1.9 (4)	C35—O34—C33—C32	1.7 (3)
C12—C8—C9—O2	157.8 (3)	C36—C32—C33—O26	161.1 (3)
C7—C8—C9—O2	−77.6 (4)	C31—C32—C33—O26	−73.9 (4)
C12—C8—C9—O10	−22.1 (3)	C36—C32—C33—O34	−20.9 (3)
C7—C8—C9—O10	102.5 (3)	C31—C32—C33—O34	104.1 (3)
C9—O10—C11—C12	19.7 (3)	C33—O34—C35—C36	18.6 (3)
O10—C11—C12—C4	−155.2 (2)	O27—C28—C36—C35	−45.8 (3)
O10—C11—C12—C8	−31.6 (3)	C29—C28—C36—C35	75.6 (4)
O10—C11—C12—C13	86.0 (3)	O27—C28—C36—C32	−160.4 (3)
O3—C4—C12—C11	−45.2 (3)	C29—C28—C36—C32	−39.1 (4)
C5—C4—C12—C11	73.4 (4)	O27—C28—C36—C37	72.1 (3)
O3—C4—C12—C8	−159.7 (3)	C29—C28—C36—C37	−166.6 (3)
C5—C4—C12—C8	−41.0 (4)	O34—C35—C36—C28	−153.6 (3)
O3—C4—C12—C13	73.4 (3)	O34—C35—C36—C32	−29.9 (3)
C5—C4—C12—C13	−168.0 (3)	O34—C35—C36—C37	88.8 (3)
C9—C8—C12—C11	31.3 (3)	C33—C32—C36—C28	150.4 (3)
C7—C8—C12—C11	−88.9 (3)	C31—C32—C36—C28	31.3 (4)
C9—C8—C12—C4	152.9 (3)	C33—C32—C36—C35	29.6 (3)
C7—C8—C12—C4	32.8 (4)	C31—C32—C36—C35	−89.5 (3)
C9—C8—C12—C13	−82.5 (3)	C33—C32—C36—C37	−85.0 (3)
C7—C8—C12—C13	157.3 (3)	C31—C32—C36—C37	155.8 (3)
C11—C12—C13—C14	−151.4 (3)	C28—C36—C37—C38	87.4 (3)
C4—C12—C13—C14	86.5 (3)	C35—C36—C37—C38	−152.1 (3)
C8—C12—C13—C14	−42.2 (4)	C32—C36—C37—C38	−41.7 (4)
C11—C12—C13—C1	79.4 (3)	C28—C36—C37—C25	−40.9 (3)
C4—C12—C13—C1	−42.6 (3)	C35—C36—C37—C25	79.6 (3)
C8—C12—C13—C1	−171.4 (3)	C32—C36—C37—C25	−170.0 (3)
C2—C1—C13—C14	−137.5 (3)	C26—C25—C37—C38	−135.5 (3)
C19—C1—C13—C14	−8.4 (3)	C42—C25—C37—C38	101.5 (3)
C18—C1—C13—C14	99.3 (3)	C43—C25—C37—C38	−6.1 (3)
C2—C1—C13—C12	−6.4 (3)	C26—C25—C37—C36	−5.3 (4)
C19—C1—C13—C12	122.6 (3)	C42—C25—C37—C36	−128.3 (3)
C18—C1—C13—C12	−129.7 (3)	C43—C25—C37—C36	124.1 (3)
C12—C13—C14—O4	−46.0 (4)	C36—C37—C38—O28	−52.3 (4)
C1—C13—C14—O4	80.9 (3)	C25—C37—C38—O28	75.1 (3)
C12—C13—C14—C15	−170.3 (2)	C36—C37—C38—C39	−175.2 (3)
C1—C13—C14—C15	−43.5 (3)	C25—C37—C38—C39	−47.8 (4)
O4—C14—C15—C16	−86.0 (3)	O28—C38—C39—C40	−81.6 (4)
C13—C14—C15—C16	37.0 (4)	C37—C38—C39—C40	40.5 (4)
C14—C15—C16—C17	−90.0 (3)	C38—C39—C40—C41	−90.6 (4)
C14—C15—C16—C19	21.8 (4)	C38—C39—C40—C43	21.0 (4)
C19—C16—C17—C20	152.3 (4)	C43—C40—C41—C44	155.4 (4)
C15—C16—C17—C20	−91.3 (4)	C39—C40—C41—C44	−89.1 (5)
C19—C16—C17—C18	−28.4 (3)	C43—C40—C41—C42	−26.6 (4)
C15—C16—C17—C18	88.1 (3)	C39—C40—C41—C42	88.9 (3)
C20—C17—C18—O5	4.3 (6)	C44—C41—C42—O29	0.5 (6)
C16—C17—C18—O5	−175.1 (3)	C40—C41—C42—O29	−177.6 (4)
C20—C17—C18—C1	−179.7 (3)	C44—C41—C42—C25	177.1 (4)
C16—C17—C18—C1	0.9 (3)	C40—C41—C42—C25	−1.0 (4)
C2—C1—C18—O5	−38.6 (4)	C26—C25—C42—O29	−35.7 (5)
C19—C1—C18—O5	−157.4 (3)	C43—C25—C42—O29	−155.6 (4)
C13—C1—C18—O5	88.0 (4)	C37—C25—C42—O29	90.7 (4)
C2—C1—C18—C17	145.3 (3)	C26—C25—C42—C41	147.6 (3)
C19—C1—C18—C17	26.5 (3)	C43—C25—C42—C41	27.7 (3)
C13—C1—C18—C17	−88.1 (3)	C37—C25—C42—C41	−86.0 (3)
C23—O6—C19—C16	−153.8 (3)	C47—O30—C43—C40	−153.7 (3)
C23—O6—C19—C1	96.7 (3)	C47—O30—C43—C25	97.0 (3)
C17—C16—C19—O6	−70.5 (3)	C41—C40—C43—O30	−71.2 (3)
C15—C16—C19—O6	171.7 (3)	C39—C40—C43—O30	171.1 (3)
C17—C16—C19—C1	44.7 (3)	C41—C40—C43—C25	43.4 (3)
C15—C16—C19—C1	−73.1 (3)	C39—C40—C43—C25	−74.3 (3)
C2—C1—C19—O6	−49.6 (3)	C26—C25—C43—O30	−49.4 (3)
C18—C1—C19—O6	69.2 (3)	C42—C25—C43—O30	69.4 (3)
C13—C1—C19—O6	178.6 (2)	C37—C25—C43—O30	179.0 (2)
C2—C1—C19—C16	−162.6 (3)	C26—C25—C43—C40	−162.6 (3)
C18—C1—C19—C16	−43.8 (3)	C42—C25—C43—C40	−43.8 (3)
C13—C1—C19—C16	65.7 (3)	C37—C25—C43—C40	65.8 (3)
C19—O6—C23—O7	1.1 (5)	C43—O30—C47—O31	1.2 (6)
C19—O6—C23—C24	−178.7 (3)	C43—O30—C47—C48	−176.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O28—H28A···O1^i	0.81 (2)	1.93 (2)	2.711 (3)	161 (4)
O4—H4A···O26	0.84 (2)	2.20 (3)	2.957 (4)	150 (4)

Symmetry code: (i) x+1, y, z.