A stereoisomer of bharangin tri­acetate

A stereoisomer of bharangin tri­acetate [systematic name: 6,10-bis­(acetyl­oxy)-8-iso­propyl-4,4,11a-tri­methyl-2-oxo-2,3,4,6,11,11a-hexa­hydro­benzo­[5,6]­cyclo­hepta­[1,2-b]­pyran-9-yl acetate], C₂₆H₃₂O₈, a tricyclic diterpenoid, is reported. There is a 0.56 (3):0.44 (3) disorder in the terminal iso­propyl side chain. The title compound and a previously reported stereoisomer, crystallizing in the same space group, exhibit very similar molecular conformations, but differ in the orientation of one of the acetate groups, resulting in a different configuration at the atom to which the acetate group is attached. Consequently, different C—H...O interactions are observed.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.060
• wR factor = 0.158
• Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found





Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.77 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.56 Ratio

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.83 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C23
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      35.80 Deg.
              H20B -C20  -H20A    1.555   1.555   1.555

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           24.99
           From the CIF: _reflns_number_total               2719
           Count of symmetry unique reflns         2718
           Completeness (_total/calc)            100.04%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         1
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 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
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

6,10-bis(acetyloxy)-8-isopropyl-4,4,11a-trimethyl-2-oxo-2,3,4,6,11,11a- hexahydrobenzo[5,6]cyclohepta[1,2-b]pyran-9-yl acetate

Crystal data

C26H32O8	F(000) = 1008
Mr = 472.52	Dx = 1.162 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5772 reflections
a = 8.1986 (5) Å	θ = 2.5–21.6°
b = 14.0252 (9) Å	µ = 0.09 mm^−1
c = 23.482 (1) Å	T = 273 K
V = 2700.1 (3) Å^3	Needle, colorless
Z = 4	0.27 × 0.15 × 0.10 mm

Data collection

CCD Area Detector diffractometer	2554 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 25.0°, θmin = 1.7°
ω scans	h = −9→9
19633 measured reflections	k = −16→16
2719 independent reflections	l = −27→27

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.158	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0888P)^2 + 1.0606P] where P = (Fo^2 + 2Fc^2)/3
2719 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 0.29 e Å^−3
44 restraints	Δρmin = −0.30 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.9218 (4)	1.04915 (18)	0.75588 (12)	0.0521 (7)
O2	1.1214 (5)	1.0795 (3)	0.69701 (18)	0.0867 (13)
O3	0.5773 (3)	0.73497 (16)	0.85360 (10)	0.0368 (6)
O4	0.5227 (5)	0.6842 (2)	0.76589 (13)	0.0678 (10)
O5	0.4255 (4)	1.1151 (2)	0.98604 (13)	0.0595 (8)
O6	0.6763 (6)	1.1290 (4)	1.0202 (2)	0.1040 (16)
O7	0.5563 (3)	1.16213 (17)	0.88405 (12)	0.0466 (7)
O8	0.2926 (4)	1.1653 (3)	0.85900 (18)	0.0749 (10)
C1	0.6224 (4)	0.8274 (2)	0.83164 (14)	0.0321 (7)
H1	0.5567	0.8391	0.7975	0.039*
C2	0.7983 (4)	0.8245 (2)	0.81362 (15)	0.0350 (8)
H2	0.8422	0.7636	0.8102	0.042*
C3	0.9003 (4)	0.8944 (2)	0.80185 (14)	0.0329 (7)
C4	0.8617 (5)	1.0004 (2)	0.80712 (16)	0.0362 (8)
C5	0.6791 (5)	1.0225 (2)	0.80508 (15)	0.0374 (8)
H5A	0.6640	1.0899	0.7976	0.045*
H5B	0.6298	0.9873	0.7740	0.045*
C6	0.5940 (4)	0.9970 (2)	0.85961 (15)	0.0353 (7)
C7	0.5752 (4)	0.9014 (2)	0.87532 (14)	0.0357 (8)
C8	0.5082 (5)	0.8783 (3)	0.92742 (17)	0.0477 (10)
H8	0.4941	0.8144	0.9366	0.057*
C9	0.4612 (6)	0.9469 (3)	0.96636 (18)	0.0570 (11)
C10	0.4766 (5)	1.0414 (3)	0.94995 (17)	0.0468 (9)
C11	0.5401 (5)	1.0649 (3)	0.89755 (17)	0.0427 (9)
C12	1.0706 (5)	0.8691 (3)	0.7793 (2)	0.0529 (10)
C13	1.1707 (5)	0.9602 (3)	0.7675 (2)	0.0578 (11)
H13A	1.2090	0.9861	0.8034	0.069*
H13B	1.2654	0.9437	0.7449	0.069*
C14	1.0750 (6)	1.0338 (3)	0.73731 (19)	0.0549 (11)
C15	1.1612 (6)	0.8071 (5)	0.8217 (4)	0.120 (3)
H15A	1.1713	0.8405	0.8572	0.144*
H15B	1.2678	0.7927	0.8071	0.144*
H15C	1.1018	0.7489	0.8275	0.144*
C16	1.0529 (8)	0.8165 (4)	0.7221 (3)	0.096 (2)
H16A	1.1587	0.7975	0.7087	0.115*
H16B	1.0032	0.8581	0.6947	0.115*
H16C	0.9859	0.7610	0.7272	0.115*
C17	0.9363 (6)	1.0455 (3)	0.8599 (2)	0.0596 (11)
H17A	1.0527	1.0383	0.8588	0.071*
H17B	0.8942	1.0146	0.8933	0.071*
H17C	0.9091	1.1120	0.8610	0.071*
C18	0.5282 (5)	0.6696 (3)	0.81581 (17)	0.0436 (9)
C19	0.4798 (7)	0.5794 (3)	0.8440 (2)	0.0677 (14)
H19A	0.4055	0.5452	0.8199	0.081*
H19B	0.4277	0.5934	0.8796	0.081*
H19C	0.5750	0.5411	0.8507	0.081*
C20	0.3911 (12)	0.9211 (5)	1.0237 (3)	0.118 (2)
H20B	0.3988	0.9751	1.0501	0.142*	0.56
H20A	0.3316	0.9755	1.0397	0.142*	0.44
C21A	0.289 (2)	0.8384 (9)	1.0268 (5)	0.118 (2)	0.56
H21A	0.2514	0.8299	1.0652	0.178*	0.56
H21B	0.3492	0.7833	1.0151	0.178*	0.56
H21C	0.1963	0.8467	1.0021	0.178*	0.56
C22A	0.5460 (18)	0.8967 (9)	1.0620 (4)	0.118 (2)	0.56
H22A	0.6191	0.9501	1.0623	0.178*	0.56
H22B	0.6009	0.8420	1.0467	0.178*	0.56
H22C	0.5111	0.8832	1.1002	0.178*	0.56
C21B	0.201 (2)	0.9007 (12)	1.0098 (6)	0.118 (2)	0.44
H21D	0.1543	0.9552	0.9911	0.178*	0.44
H21E	0.1431	0.8888	1.0447	0.178*	0.44
H21F	0.1920	0.8460	0.9854	0.178*	0.44
C22B	0.436 (3)	0.8315 (11)	1.0502 (6)	0.118 (2)	0.44
H22D	0.3819	0.8256	1.0862	0.178*	0.44
H22E	0.5523	0.8300	1.0560	0.178*	0.44
H22F	0.4050	0.7797	1.0258	0.178*	0.44
C23	0.5427 (8)	1.1553 (4)	1.0197 (2)	0.0705 (14)
C24	0.4707 (10)	1.2372 (5)	1.0523 (3)	0.106 (2)
H24A	0.5379	1.2510	1.0847	0.128*
H24B	0.3629	1.2207	1.0648	0.128*
H24C	0.4654	1.2924	1.0281	0.128*
C25	0.4162 (6)	1.2058 (3)	0.86569 (18)	0.0502 (10)
C26	0.4456 (8)	1.3102 (3)	0.8563 (3)	0.0751 (15)
H26A	0.3430	1.3431	0.8547	0.090*
H26B	0.5031	1.3192	0.8211	0.090*
H26C	0.5096	1.3352	0.8871	0.090*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0598 (18)	0.0363 (13)	0.0603 (16)	0.0041 (14)	0.0199 (15)	0.0112 (12)
O2	0.087 (3)	0.069 (2)	0.104 (3)	0.000 (2)	0.050 (2)	0.030 (2)
O3	0.0407 (13)	0.0292 (11)	0.0405 (12)	−0.0042 (11)	−0.0016 (11)	−0.0015 (10)
O4	0.092 (2)	0.0614 (19)	0.0501 (18)	−0.0311 (19)	−0.0090 (16)	−0.0103 (14)
O5	0.068 (2)	0.0526 (17)	0.0573 (16)	0.0086 (16)	0.0135 (16)	−0.0184 (14)
O6	0.083 (3)	0.108 (3)	0.121 (3)	0.025 (3)	−0.022 (3)	−0.055 (3)
O7	0.0445 (15)	0.0285 (12)	0.0669 (17)	−0.0004 (12)	0.0092 (13)	−0.0066 (12)
O8	0.0506 (18)	0.0613 (19)	0.113 (3)	−0.0035 (17)	−0.003 (2)	0.014 (2)
C1	0.0353 (17)	0.0291 (16)	0.0320 (16)	−0.0021 (14)	−0.0020 (14)	0.0013 (13)
C2	0.0386 (19)	0.0261 (16)	0.0404 (18)	0.0033 (15)	0.0009 (15)	−0.0037 (14)
C3	0.0334 (17)	0.0319 (16)	0.0336 (16)	0.0003 (15)	−0.0009 (14)	0.0014 (14)
C4	0.043 (2)	0.0250 (16)	0.0408 (18)	−0.0012 (15)	0.0050 (16)	0.0009 (14)
C5	0.047 (2)	0.0263 (16)	0.0395 (18)	0.0062 (15)	0.0027 (16)	0.0050 (15)
C6	0.0326 (16)	0.0331 (17)	0.0401 (18)	0.0026 (15)	0.0004 (15)	0.0009 (14)
C7	0.0353 (18)	0.0314 (16)	0.0405 (18)	0.0033 (15)	−0.0008 (16)	0.0017 (14)
C8	0.062 (3)	0.0331 (18)	0.048 (2)	−0.0075 (18)	0.010 (2)	0.0041 (16)
C9	0.072 (3)	0.051 (2)	0.048 (2)	0.003 (2)	0.020 (2)	−0.0029 (18)
C10	0.049 (2)	0.044 (2)	0.048 (2)	0.0005 (19)	0.0091 (18)	−0.0122 (17)
C11	0.043 (2)	0.0315 (18)	0.054 (2)	0.0035 (17)	0.0015 (18)	−0.0040 (16)
C12	0.037 (2)	0.0358 (19)	0.086 (3)	0.0022 (18)	0.011 (2)	0.0053 (19)
C13	0.040 (2)	0.052 (2)	0.081 (3)	−0.007 (2)	0.015 (2)	0.000 (2)
C14	0.055 (3)	0.041 (2)	0.068 (3)	−0.010 (2)	0.028 (2)	0.003 (2)
C15	0.033 (2)	0.111 (5)	0.218 (9)	0.013 (3)	0.010 (4)	0.091 (6)
C16	0.080 (4)	0.070 (3)	0.138 (5)	−0.019 (3)	0.066 (4)	−0.042 (3)
C17	0.053 (2)	0.059 (2)	0.067 (3)	−0.016 (2)	0.002 (2)	−0.024 (2)
C18	0.0389 (19)	0.042 (2)	0.050 (2)	−0.0069 (17)	0.0011 (17)	−0.0046 (17)
C19	0.090 (4)	0.044 (2)	0.070 (3)	−0.026 (2)	0.012 (3)	−0.010 (2)
C20	0.184 (6)	0.100 (3)	0.072 (3)	0.003 (4)	0.061 (4)	0.020 (3)
C21A	0.184 (6)	0.100 (3)	0.072 (3)	0.003 (4)	0.061 (4)	0.020 (3)
C22A	0.184 (6)	0.100 (3)	0.072 (3)	0.003 (4)	0.061 (4)	0.020 (3)
C21B	0.184 (6)	0.100 (3)	0.072 (3)	0.003 (4)	0.061 (4)	0.020 (3)
C22B	0.184 (6)	0.100 (3)	0.072 (3)	0.003 (4)	0.061 (4)	0.020 (3)
C23	0.083 (4)	0.064 (3)	0.064 (3)	0.007 (3)	0.002 (3)	−0.021 (2)
C24	0.125 (6)	0.094 (4)	0.101 (4)	0.021 (4)	−0.009 (4)	−0.054 (4)
C25	0.053 (2)	0.0378 (19)	0.060 (2)	0.010 (2)	0.018 (2)	−0.0033 (18)
C26	0.088 (4)	0.040 (2)	0.097 (4)	0.009 (3)	0.019 (3)	0.007 (2)

Geometric parameters (Å, º)

O1—C14	1.346 (5)	C15—H15B	0.9600
O1—C4	1.469 (4)	C15—H15C	0.9600
O2—C14	1.205 (5)	C16—H16A	0.9600
O3—C18	1.338 (4)	C16—H16B	0.9600
O3—C1	1.444 (4)	C16—H16C	0.9600
O4—C18	1.191 (5)	C17—H17A	0.9600
O5—C23	1.366 (7)	C17—H17B	0.9600
O5—C10	1.402 (5)	C17—H17C	0.9600
O6—C23	1.156 (7)	C18—C19	1.482 (6)
O7—C25	1.372 (5)	C19—H19A	0.9600
O7—C11	1.407 (4)	C19—H19B	0.9600
O8—C25	1.172 (5)	C19—H19C	0.9600
C1—C2	1.504 (5)	C20—C21A	1.435 (13)
C1—C7	1.509 (5)	C20—C22B	1.450 (14)
C1—H1	0.9800	C20—C22A	1.593 (14)
C2—C3	1.318 (5)	C20—C21B	1.620 (16)
C2—H2	0.9300	C20—H20B	0.9800
C3—C4	1.524 (5)	C20—H20A	0.9800
C3—C12	1.535 (5)	C21A—H21A	0.9600
C4—C17	1.520 (5)	C21A—H21B	0.9600
C4—C5	1.530 (5)	C21A—H21C	0.9600
C5—C6	1.501 (5)	C22A—H22A	0.9600
C5—H5A	0.9700	C22A—H22B	0.9600
C5—H5B	0.9700	C22A—H22C	0.9600
C6—C11	1.377 (5)	C21B—H21D	0.9600
C6—C7	1.399 (5)	C21B—H21E	0.9600
C7—C8	1.380 (5)	C21B—H21F	0.9600
C8—C9	1.382 (6)	C22B—H22D	0.9600
C8—H8	0.9300	C22B—H22E	0.9600
C9—C10	1.386 (6)	C22B—H22F	0.9600
C9—C20	1.508 (7)	C23—C24	1.501 (7)
C10—C11	1.376 (6)	C24—H24A	0.9600
C12—C15	1.516 (7)	C24—H24B	0.9600
C12—C16	1.539 (7)	C24—H24C	0.9600
C12—C13	1.543 (6)	C25—C26	1.501 (6)
C13—C14	1.479 (6)	C26—H26A	0.9600
C13—H13A	0.9700	C26—H26B	0.9600
C13—H13B	0.9700	C26—H26C	0.9600
C15—H15A	0.9600
C14—O1—C4	120.2 (3)	C4—C17—H17C	109.5
C18—O3—C1	117.1 (3)	H17A—C17—H17C	109.5
C23—O5—C10	116.4 (4)	H17B—C17—H17C	109.5
C25—O7—C11	115.1 (3)	O4—C18—O3	123.1 (4)
O3—C1—C2	108.8 (3)	O4—C18—C19	125.2 (4)
O3—C1—C7	108.0 (3)	O3—C18—C19	111.7 (3)
C2—C1—C7	117.1 (3)	C18—C19—H19A	109.5
O3—C1—H1	107.5	C18—C19—H19B	109.5
C2—C1—H1	107.5	H19A—C19—H19B	109.5
C7—C1—H1	107.5	C18—C19—H19C	109.5
C3—C2—C1	130.3 (3)	H19A—C19—H19C	109.5
C3—C2—H2	114.8	H19B—C19—H19C	109.5
C1—C2—H2	114.8	C21A—C20—C22B	55.1 (10)
C2—C3—C4	125.2 (3)	C21A—C20—C9	117.5 (7)
C2—C3—C12	118.5 (3)	C22B—C20—C9	119.5 (8)
C4—C3—C12	116.3 (3)	C21A—C20—C22A	105.4 (9)
O1—C4—C17	109.8 (3)	C22B—C20—C22A	50.8 (10)
O1—C4—C3	108.5 (3)	C9—C20—C22A	104.6 (7)
C17—C4—C3	112.9 (3)	C21A—C20—C21B	45.8 (8)
O1—C4—C5	102.0 (3)	C22B—C20—C21B	100.3 (12)
C17—C4—C5	109.6 (3)	C9—C20—C21B	103.2 (7)
C3—C4—C5	113.5 (3)	C22A—C20—C21B	147.5 (8)
C6—C5—C4	112.3 (3)	C21A—C20—H20B	129.1
C6—C5—H5A	109.1	C22B—C20—H20B	112.4
C4—C5—H5A	109.1	C9—C20—H20B	110.8
C6—C5—H5B	109.1	C22A—C20—H20B	76.0
C4—C5—H5B	109.1	C21B—C20—H20B	109.0
H5A—C5—H5B	107.9	C21A—C20—H20A	108.5
C11—C6—C7	117.2 (3)	C22B—C20—H20A	129.6
C11—C6—C5	122.5 (3)	C9—C20—H20A	110.2
C7—C6—C5	120.3 (3)	C22A—C20—H20A	110.4
C8—C7—C6	120.2 (3)	C21B—C20—H20A	74.6
C8—C7—C1	122.9 (3)	H20B—C20—H20A	35.8
C6—C7—C1	116.8 (3)	C20—C21A—H21A	109.5
C7—C8—C9	122.3 (3)	C20—C21A—H21B	109.5
C7—C8—H8	118.8	H21A—C21A—H21B	109.5
C9—C8—H8	118.8	C20—C21A—H21C	109.5
C8—C9—C10	117.1 (4)	H21A—C21A—H21C	109.5
C8—C9—C20	122.0 (4)	H21B—C21A—H21C	109.5
C10—C9—C20	120.8 (4)	C20—C22A—H22A	109.5
C11—C10—C9	120.8 (3)	C20—C22A—H22B	109.5
C11—C10—O5	118.5 (4)	H22A—C22A—H22B	109.5
C9—C10—O5	120.7 (4)	C20—C22A—H22C	109.5
C10—C11—C6	122.3 (3)	H22A—C22A—H22C	109.5
C10—C11—O7	118.0 (3)	H22B—C22A—H22C	109.5
C6—C11—O7	119.6 (3)	C20—C21B—H21D	109.5
C15—C12—C3	110.6 (4)	C20—C21B—H21E	109.5
C15—C12—C16	110.1 (5)	H21D—C21B—H21E	109.5
C3—C12—C16	109.0 (4)	C20—C21B—H21F	109.5
C15—C12—C13	109.4 (4)	H21D—C21B—H21F	109.5
C3—C12—C13	110.7 (3)	H21E—C21B—H21F	109.5
C16—C12—C13	106.9 (4)	C20—C22B—H22D	109.5
C14—C13—C12	112.5 (4)	C20—C22B—H22E	109.5
C14—C13—H13A	109.1	H22D—C22B—H22E	109.5
C12—C13—H13A	109.1	C20—C22B—H22F	109.5
C14—C13—H13B	109.1	H22D—C22B—H22F	109.5
C12—C13—H13B	109.1	H22E—C22B—H22F	109.5
H13A—C13—H13B	107.8	O6—C23—O5	122.7 (5)
O2—C14—O1	117.7 (4)	O6—C23—C24	127.7 (6)
O2—C14—C13	125.5 (4)	O5—C23—C24	109.5 (5)
O1—C14—C13	116.8 (3)	C23—C24—H24A	109.5
C12—C15—H15A	109.5	C23—C24—H24B	109.5
C12—C15—H15B	109.5	H24A—C24—H24B	109.5
H15A—C15—H15B	109.5	C23—C24—H24C	109.5
C12—C15—H15C	109.5	H24A—C24—H24C	109.5
H15A—C15—H15C	109.5	H24B—C24—H24C	109.5
H15B—C15—H15C	109.5	O8—C25—O7	123.4 (4)
C12—C16—H16A	109.5	O8—C25—C26	126.3 (5)
C12—C16—H16B	109.5	O7—C25—C26	110.3 (4)
H16A—C16—H16B	109.5	C25—C26—H26A	109.5
C12—C16—H16C	109.5	C25—C26—H26B	109.5
H16A—C16—H16C	109.5	H26A—C26—H26B	109.5
H16B—C16—H16C	109.5	C25—C26—H26C	109.5
C4—C17—H17A	109.5	H26A—C26—H26C	109.5
C4—C17—H17B	109.5	H26B—C26—H26C	109.5
H17A—C17—H17B	109.5
C18—O3—C1—C2	−85.7 (4)	C9—C10—C11—C6	−1.4 (7)
C18—O3—C1—C7	146.3 (3)	O5—C10—C11—C6	179.6 (4)
O3—C1—C2—C3	−165.1 (4)	C9—C10—C11—O7	−178.4 (4)
C7—C1—C2—C3	−42.4 (5)	O5—C10—C11—O7	2.6 (6)
C1—C2—C3—C4	3.4 (6)	C7—C6—C11—C10	2.8 (6)
C1—C2—C3—C12	−174.7 (3)	C5—C6—C11—C10	−173.5 (4)
C14—O1—C4—C17	74.6 (4)	C7—C6—C11—O7	179.8 (3)
C14—O1—C4—C3	−49.2 (4)	C5—C6—C11—O7	3.5 (6)
C14—O1—C4—C5	−169.2 (3)	C25—O7—C11—C10	−80.8 (5)
C2—C3—C4—O1	−135.0 (4)	C25—O7—C11—C6	102.1 (4)
C12—C3—C4—O1	43.1 (4)	C2—C3—C12—C15	−59.2 (6)
C2—C3—C4—C17	103.0 (4)	C4—C3—C12—C15	122.6 (5)
C12—C3—C4—C17	−78.8 (4)	C2—C3—C12—C16	62.1 (5)
C2—C3—C4—C5	−22.4 (5)	C4—C3—C12—C16	−116.2 (4)
C12—C3—C4—C5	155.8 (3)	C2—C3—C12—C13	179.4 (4)
O1—C4—C5—C6	−168.3 (3)	C4—C3—C12—C13	1.1 (5)
C17—C4—C5—C6	−52.0 (4)	C15—C12—C13—C14	−166.9 (5)
C3—C4—C5—C6	75.2 (4)	C3—C12—C13—C14	−44.7 (5)
C4—C5—C6—C11	107.2 (4)	C16—C12—C13—C14	73.9 (5)
C4—C5—C6—C7	−69.0 (5)	C4—O1—C14—O2	−175.9 (4)
C11—C6—C7—C8	−1.3 (5)	C4—O1—C14—C13	5.5 (5)
C5—C6—C7—C8	175.1 (4)	C12—C13—C14—O2	−134.5 (5)
C11—C6—C7—C1	175.3 (3)	C12—C13—C14—O1	43.9 (6)
C5—C6—C7—C1	−8.3 (5)	C1—O3—C18—O4	1.0 (6)
O3—C1—C7—C8	2.8 (5)	C1—O3—C18—C19	−177.9 (4)
C2—C1—C7—C8	−120.4 (4)	C8—C9—C20—C21A	−35.7 (13)
O3—C1—C7—C6	−173.8 (3)	C10—C9—C20—C21A	142.5 (10)
C2—C1—C7—C6	63.1 (4)	C8—C9—C20—C22B	27.8 (16)
C6—C7—C8—C9	−1.6 (6)	C10—C9—C20—C22B	−154.1 (13)
C1—C7—C8—C9	−178.1 (4)	C8—C9—C20—C22A	80.7 (8)
C7—C8—C9—C10	3.1 (7)	C10—C9—C20—C22A	−101.1 (8)
C7—C8—C9—C20	−178.7 (6)	C8—C9—C20—C21B	−82.4 (9)
C8—C9—C10—C11	−1.6 (7)	C10—C9—C20—C21B	95.7 (9)
C20—C9—C10—C11	−179.8 (6)	C10—O5—C23—O6	−2.2 (8)
C8—C9—C10—O5	177.4 (4)	C10—O5—C23—C24	175.9 (5)
C20—C9—C10—O5	−0.8 (8)	C11—O7—C25—O8	−3.3 (6)
C23—O5—C10—C11	−85.7 (5)	C11—O7—C25—C26	176.3 (3)
C23—O5—C10—C9	95.3 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3	0.93	2.35	2.714 (5)	103
C5—H5A···O7	0.97	2.43	2.879 (4)	108
C5—H5A···O4^i	0.97	2.51	3.265 (4)	134

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