A cocrystal of clusiacitran A, clusiacitran B, fluorinated clusiacitran A and fluorinated clusiacitran B (0.45:0.45:0.05:0.05)

The title cocrystal, 0.45C₂₃H₂₄O₄·0.45C₂₃H₂₄O₄·0.05C₂₃H₂₃FO₄·0.05C₂₃H₂₃FO₄, is a disordered mixture of four compounds, viz. clusiacitran A [(9-hydr­oxy-1,5,5-trimethyl-6,15-dioxatetra­cyclo­[9.3.10^4,13.0^7,12]penta­deca-7,9,11-trien-8-­yl)(phen­yl)methanone], clusiacitran B [(9-hydr­oxy-1,5,5-trimethyl-6,15-dioxatetra­cyclo­[9.3.10^4,13.0^7,12]penta­deca-7,9,11-trien-10-­yl)(phen­yl)methanone], fluorinated clusiacitran A {(10-fluoro-9-hydr­oxy-1,5,5-trimethyl-6,15-dioxatetra­cyclo­[9.3.10^4,13.0^7,12]penta­deca-7,9,11-trien-8-­yl)(phen­yl)meth­anone} and fluorinated clusiacitran B, {(10-fluoro-9-hydr­oxy-1,5,5-trimethyl-6,15-dioxatetra­cyclo­[9.3.10^4,13.0^7,12]penta­deca-7,9,11-trien-10-­yl)(phen­yl)methanone}, which were isolated from Garcinia schomburgkiana Pierre. In all the components, the cyclo­hexane rings adopt half-chair conformations. O—H...O intra­molecular hydrogen bonds are observed. In the crystal structure, the mol­ecules are linked via C—H...O inter­molecular inter­actions, forming chains along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.057
• wR factor = 0.135
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O2
PLAT432_ALERT_2_B Short Inter X...Y Contact  C3     ..  F1      ..       2.84 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C4     ..  F1      ..       2.70 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.72 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT301_ALERT_3_C Main Residue  Disorder .........................      18.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

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

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

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

clusiacitran A–clusiacitran B– (10-fluoro-9-hydroxy-1,5,5-trimethyl-6,15- dioxatetracyclo[9.3.10^4,13.0^7,12]pentadeca-7,9,11-trien-8- yl)(phenyl)methanone– (10-fluoro-9-hydroxy-1,5,5-trimethyl-6,15- dioxatetracyclo[9.3.10^4,13.0^7,12]pentadeca-7,9,11-trien-10- yl)(phenyl)methanone (0.45/0.45/0.05/0.05)

Crystal data

0.45C23H24O4·0.45C23H24O4·0.05C23H23FO4·0.05C23H23FO4	F(000) = 779.2
Mr = 366.24	Dx = 1.293 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4330 reflections
a = 9.6691 (2) Å	θ = 2.2–27.5°
b = 10.5583 (2) Å	µ = 0.09 mm^−1
c = 18.9279 (3) Å	T = 100 K
β = 103.160 (1)°	Needle, yellow
V = 1881.59 (6) Å^3	0.42 × 0.13 × 0.11 mm
Z = 4

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	4330 independent reflections
Radiation source: fine-focus sealed tube	2691 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 8.33 pixels mm^-1	θmax = 27.5°, θmin = 2.2°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→13
Tmin = 0.986, Tmax = 0.991	l = −24→24
22779 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0489P)^2 + 0.5555P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
4330 reflections	Δρmax = 0.25 e Å^−3
317 parameters	Δρmin = −0.22 e Å^−3
1 restraint	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (7)

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.82345 (14)	0.38791 (13)	0.20713 (7)	0.0463 (4)
O2	0.7644 (2)	0.26442 (14)	−0.00561 (8)	0.0719 (6)
O3	0.63335 (17)	0.66797 (16)	−0.09223 (8)	0.0655 (5)
O4	0.74149 (13)	0.60456 (12)	0.15921 (7)	0.0396 (4)
H1O4	0.7721	0.5498	0.1894	0.059*
C1	0.7768 (2)	0.20003 (18)	0.14073 (10)	0.0366 (5)
C2	0.6577 (2)	0.13662 (18)	0.10279 (11)	0.0408 (5)
H2B	0.5803	0.1822	0.0768	0.049*
C3	0.6531 (2)	0.00565 (19)	0.10334 (12)	0.0480 (5)
H3A	0.5722	−0.0368	0.0787	0.058*
C4	0.7701 (3)	−0.0622 (2)	0.14092 (12)	0.0528 (6)
H4A	0.7682	−0.1503	0.1405	0.063*
C5	0.8884 (3)	0.0005 (2)	0.17863 (12)	0.0524 (6)
H5A	0.9667	−0.0454	0.2033	0.063*
C6	0.8917 (2)	0.1308 (2)	0.18015 (10)	0.0435 (5)
H6A	0.9706	0.1727	0.2075	0.052*
C7	0.78273 (19)	0.34106 (19)	0.14513 (10)	0.0367 (5)
C8	0.73865 (19)	0.42204 (18)	0.08205 (9)	0.0332 (4)
C9	0.71778 (18)	0.55371 (18)	0.09205 (10)	0.0322 (4)
C10	0.67817 (19)	0.6356 (2)	0.03366 (10)	0.0371 (5)
H10A	0.6688	0.7220	0.0410	0.16 (3)*	0.899 (6)
F1	0.6614 (12)	0.7653 (9)	0.0377 (6)	0.054 (6)	0.101 (6)
C11	0.65296 (19)	0.5859 (2)	−0.03559 (10)	0.0393 (5)
C12	0.65582 (18)	0.4566 (2)	−0.04853 (10)	0.0356 (5)
C13	0.7163 (2)	0.38013 (18)	0.00862 (10)	0.0374 (5)
C14	0.8071 (2)	0.24259 (19)	−0.07372 (11)	0.0412 (5)
C15A	0.7796 (4)	0.3646 (4)	−0.12604 (19)	0.0368 (10)	0.506 (2)
H15A	0.7755	0.3340	−0.1754	0.044*	0.506 (2)
C15B	0.7294 (4)	0.4810 (4)	−0.1590 (2)	0.0361 (10)	0.494 (2)
H15B	0.7229	0.4514	−0.2087	0.043*	0.494 (2)
C16	0.63186 (19)	0.4082 (2)	−0.12435 (10)	0.0378 (5)
H16A	0.5651	0.3395	−0.1329	0.045*	0.506 (2)
H16B	0.5354	0.4247	−0.1493	0.045*	0.494 (2)
C17A	0.5835 (4)	0.5218 (4)	−0.1802 (2)	0.0423 (11)	0.506 (2)
H17A	0.5872	0.4949	−0.2287	0.051*	0.506 (2)
H17B	0.4865	0.5459	−0.1806	0.051*	0.506 (2)
C17B	0.6627 (4)	0.2590 (4)	−0.1258 (2)	0.0417 (11)	0.494 (2)
H17C	0.5902	0.2110	−0.1095	0.050*	0.494 (2)
H17D	0.6658	0.2314	−0.1743	0.050*	0.494 (2)
C18	0.6761 (2)	0.6276 (2)	−0.15898 (10)	0.0444 (5)
C19A	0.8332 (4)	0.5997 (4)	−0.1486 (2)	0.0423 (11)	0.506 (2)
H19A	0.8861	0.6661	−0.1188	0.051*	0.506 (2)
H19D	0.8572	0.6036	−0.1956	0.051*	0.506 (2)
C19B	0.9175 (4)	0.3162 (4)	−0.0989 (2)	0.0425 (11)	0.494 (2)
H19B	0.9302	0.2792	−0.1439	0.051*	0.494 (2)
H19C	1.0066	0.3071	−0.0634	0.051*	0.494 (2)
C20	0.88502 (19)	0.4660 (2)	−0.11233 (11)	0.0415 (5)
H20A	0.9145	0.4779	−0.0608	0.050*	0.506 (2)
H20B	0.9668	0.4393	−0.1292	0.050*	0.506 (2)
H20C	0.9515	0.5028	−0.1371	0.050*	0.494 (2)
H20D	0.8938	0.5086	−0.0667	0.050*	0.494 (2)
C21A	0.7419 (5)	0.1298 (4)	−0.1101 (3)	0.0524 (12)	0.506 (2)
H21A	0.7470	0.0626	−0.0754	0.079*	0.506 (2)
H21B	0.7911	0.1050	−0.1466	0.079*	0.506 (2)
H21C	0.6442	0.1469	−0.1325	0.079*	0.506 (2)
C21B	0.5507 (5)	0.6400 (5)	−0.2254 (2)	0.0560 (13)	0.494 (2)
H21D	0.5052	0.7204	−0.2240	0.084*	0.494 (2)
H21E	0.4836	0.5733	−0.2245	0.084*	0.494 (2)
H21F	0.5851	0.6339	−0.2690	0.084*	0.494 (2)
C22A	0.9639 (4)	0.2293 (4)	−0.0372 (2)	0.0473 (11)	0.506 (2)
H22A	0.9771	0.1571	−0.0056	0.071*	0.506 (2)
H22B	0.9956	0.3043	−0.0095	0.071*	0.506 (2)
H22C	1.0178	0.2183	−0.0735	0.071*	0.506 (2)
C22B	0.7894 (5)	0.7174 (4)	−0.1610 (3)	0.0534 (12)	0.494 (2)
H22D	0.7523	0.8020	−0.1637	0.080*	0.494 (2)
H22E	0.8273	0.7008	−0.2027	0.080*	0.494 (2)
H22F	0.8633	0.7085	−0.1178	0.080*	0.494 (2)
C23A	0.6375 (5)	0.7503 (5)	−0.2069 (2)	0.0577 (13)	0.506 (2)
H23A	0.6987	0.8185	−0.1858	0.087*	0.506 (2)
H23B	0.5405	0.7732	−0.2092	0.087*	0.506 (2)
H23C	0.6497	0.7339	−0.2550	0.087*	0.506 (2)
C23B	0.8483 (6)	0.0958 (4)	−0.0701 (3)	0.0609 (14)	0.494 (2)
H23D	0.9396	0.0844	−0.0378	0.091*	0.494 (2)
H23E	0.8517	0.0665	−0.1177	0.091*	0.494 (2)
H23F	0.7783	0.0482	−0.0526	0.091*	0.494 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0508 (9)	0.0518 (9)	0.0347 (8)	0.0013 (7)	0.0061 (7)	0.0039 (7)
O2	0.1473 (17)	0.0335 (9)	0.0510 (9)	−0.0005 (10)	0.0564 (11)	0.0005 (7)
O3	0.0760 (11)	0.0814 (12)	0.0478 (9)	0.0441 (9)	0.0325 (8)	0.0317 (9)
O4	0.0421 (8)	0.0415 (8)	0.0355 (7)	−0.0032 (6)	0.0093 (6)	−0.0026 (6)
C1	0.0396 (11)	0.0393 (12)	0.0349 (10)	0.0044 (9)	0.0168 (9)	0.0082 (9)
C2	0.0430 (11)	0.0389 (12)	0.0428 (11)	0.0042 (10)	0.0145 (9)	0.0091 (9)
C3	0.0597 (14)	0.0385 (13)	0.0486 (13)	−0.0028 (11)	0.0181 (11)	0.0066 (10)
C4	0.0769 (17)	0.0361 (12)	0.0507 (14)	0.0117 (12)	0.0257 (13)	0.0117 (11)
C5	0.0616 (15)	0.0518 (15)	0.0475 (13)	0.0218 (12)	0.0202 (12)	0.0147 (11)
C6	0.0436 (12)	0.0508 (14)	0.0390 (11)	0.0066 (10)	0.0158 (9)	0.0108 (10)
C7	0.0333 (10)	0.0463 (12)	0.0323 (11)	0.0012 (9)	0.0111 (8)	0.0029 (9)
C8	0.0331 (10)	0.0372 (11)	0.0296 (10)	−0.0043 (8)	0.0078 (8)	0.0021 (8)
C9	0.0246 (9)	0.0406 (11)	0.0326 (10)	−0.0044 (8)	0.0090 (8)	−0.0008 (9)
C10	0.0313 (10)	0.0389 (12)	0.0435 (12)	0.0029 (9)	0.0138 (9)	0.0061 (9)
F1	0.049 (8)	0.079 (12)	0.043 (8)	−0.018 (6)	0.026 (6)	−0.020 (6)
C11	0.0266 (10)	0.0560 (14)	0.0377 (11)	0.0099 (9)	0.0120 (8)	0.0148 (10)
C12	0.0238 (9)	0.0524 (13)	0.0325 (10)	−0.0073 (9)	0.0107 (8)	0.0015 (9)
C13	0.0411 (11)	0.0353 (11)	0.0385 (11)	−0.0097 (9)	0.0148 (9)	0.0001 (9)
C14	0.0423 (11)	0.0458 (12)	0.0396 (11)	0.0016 (10)	0.0178 (9)	−0.0018 (9)
C15A	0.033 (2)	0.051 (3)	0.0285 (19)	−0.0072 (19)	0.0117 (16)	−0.0040 (18)
C15B	0.032 (2)	0.045 (2)	0.033 (2)	0.0001 (18)	0.0114 (17)	0.0003 (18)
C16	0.0269 (9)	0.0560 (13)	0.0310 (10)	−0.0030 (9)	0.0078 (8)	0.0031 (9)
C17A	0.030 (2)	0.066 (3)	0.031 (2)	−0.002 (2)	0.0058 (17)	0.0104 (19)
C17B	0.044 (2)	0.042 (2)	0.044 (2)	−0.0105 (19)	0.0174 (19)	−0.0067 (19)
C18	0.0398 (11)	0.0606 (14)	0.0351 (11)	0.0039 (11)	0.0135 (9)	0.0153 (10)
C19A	0.038 (2)	0.055 (3)	0.038 (2)	−0.004 (2)	0.0180 (18)	0.008 (2)
C19B	0.038 (2)	0.048 (3)	0.044 (2)	0.0083 (19)	0.0156 (19)	0.005 (2)
C20	0.0288 (10)	0.0575 (13)	0.0417 (11)	−0.0015 (9)	0.0152 (9)	0.0112 (10)
C21A	0.054 (3)	0.056 (3)	0.051 (3)	−0.011 (2)	0.022 (2)	−0.016 (2)
C21B	0.059 (3)	0.071 (3)	0.040 (3)	0.017 (3)	0.015 (2)	0.016 (2)
C22A	0.041 (2)	0.045 (3)	0.057 (3)	0.0060 (19)	0.014 (2)	−0.006 (2)
C22B	0.067 (3)	0.043 (3)	0.055 (3)	−0.001 (2)	0.024 (2)	0.008 (2)
C23A	0.059 (3)	0.068 (3)	0.048 (3)	0.009 (3)	0.018 (2)	0.032 (2)
C23B	0.081 (4)	0.044 (3)	0.068 (3)	0.011 (3)	0.039 (3)	0.002 (2)

Geometric parameters (Å, º)

O1—C7	1.252 (2)	C16—C17A	1.597 (4)
O2—C13	1.356 (2)	C16—C17B	1.604 (4)
O2—C14	1.459 (2)	C16—H16A	0.96
O3—C11	1.358 (2)	C16—H16B	0.96
O3—C18	1.479 (2)	C17A—C18	1.431 (4)
O4—C9	1.351 (2)	C17A—H17A	0.97
O4—H1O4	0.82	C17A—H17B	0.97
C1—C2	1.384 (3)	C17B—H16A	1.2544
C1—C6	1.396 (3)	C17B—H17C	0.97
C1—C7	1.492 (3)	C17B—H17D	0.97
C2—C3	1.384 (3)	C18—C22B	1.455 (5)
C2—H2B	0.93	C18—C19A	1.516 (4)
C3—C4	1.390 (3)	C18—C21B	1.541 (5)
C3—H3A	0.93	C18—C23A	1.576 (4)
C4—C5	1.372 (3)	C19A—C20	1.600 (4)
C4—H4A	0.93	C19A—H19A	0.97
C5—C6	1.376 (3)	C19A—H19D	0.97
C5—H5A	0.93	C19B—C20	1.621 (4)
C6—H6A	0.93	C19B—H19B	0.97
C7—C8	1.451 (3)	C19B—H19C	0.97
C8—C9	1.424 (3)	C20—H20A	0.96
C8—C13	1.427 (3)	C20—H20B	0.96
C9—C10	1.387 (3)	C20—H20C	0.96
C10—C11	1.381 (3)	C20—H20D	0.96
C10—F1	1.383 (10)	C21A—H21A	0.96
C10—H10A	0.93	C21A—H21B	0.96
C11—C12	1.389 (3)	C21A—H21C	0.96
C12—C13	1.370 (3)	C21B—H21D	0.96
C12—C16	1.491 (3)	C21B—H21E	0.96
C14—C21A	1.447 (5)	C21B—H21F	0.96
C14—C19B	1.484 (4)	C22A—H22A	0.96
C14—C22A	1.523 (4)	C22A—H22B	0.96
C14—C17B	1.524 (4)	C22A—H22C	0.96
C14—C23B	1.598 (5)	C22B—H22D	0.96
C14—C15A	1.610 (4)	C22B—H22E	0.96
C15A—C20	1.460 (4)	C22B—H22F	0.96
C15A—C16	1.508 (4)	C23A—H23A	0.96
C15A—H15A	0.98	C23A—H23B	0.96
C15B—C16	1.481 (4)	C23A—H23C	0.96
C15B—C20	1.570 (4)	C23B—H23D	0.96
C15B—C18	1.632 (4)	C23B—H23E	0.96
C15B—H15B	0.98	C23B—H23F	0.96
C13—O2—C14	119.78 (15)	H16B—C17A—H17A	106.6
C11—O3—C18	118.35 (16)	C18—C17A—H17B	109.8
C9—O4—H1O4	109.5	C16—C17A—H17B	109.8
C2—C1—C6	119.43 (19)	H17A—C17A—H17B	108.3
C2—C1—C7	121.92 (17)	C14—C17B—C16	104.3 (2)
C6—C1—C7	118.52 (18)	C14—C17B—H16A	134.6
C3—C2—C1	120.25 (19)	C14—C17B—H17C	110.9
C3—C2—H2B	119.9	C16—C17B—H17C	110.9
C1—C2—H2B	119.9	C14—C17B—H17D	110.9
C2—C3—C4	119.7 (2)	C16—C17B—H17D	110.9
C2—C3—H3A	120.1	H16A—C17B—H17D	106.7
C4—C3—H3A	120.1	H17C—C17B—H17D	108.9
C5—C4—C3	120.1 (2)	C17A—C18—C22B	158.1 (3)
C5—C4—H4A	119.9	C17A—C18—O3	100.7 (2)
C3—C4—H4A	119.9	C22B—C18—O3	101.1 (2)
C4—C5—C6	120.4 (2)	C17A—C18—C19A	115.4 (3)
C4—C5—H5A	119.8	O3—C18—C19A	114.4 (2)
C6—C5—H5A	119.8	C22B—C18—C21B	112.4 (3)
C5—C6—C1	120.0 (2)	O3—C18—C21B	110.6 (2)
C5—C6—H6A	120.0	C19A—C18—C21B	134.5 (3)
C1—C6—H6A	120.0	C17A—C18—C23A	115.4 (3)
O1—C7—C8	120.62 (18)	O3—C18—C23A	100.3 (2)
O1—C7—C1	116.54 (17)	C19A—C18—C23A	109.5 (2)
C8—C7—C1	122.80 (17)	C22B—C18—C15B	112.2 (3)
C9—C8—C13	115.95 (17)	O3—C18—C15B	115.03 (19)
C9—C8—C7	119.33 (16)	C21B—C18—C15B	105.7 (3)
C13—C8—C7	124.71 (18)	C23A—C18—C15B	144.4 (3)
O4—C9—C10	117.34 (17)	C18—C19A—C20	115.7 (2)
O4—C9—C8	120.97 (16)	C18—C19A—H19A	108.4
C10—C9—C8	121.65 (17)	C20—C19A—H19A	108.4
C11—C10—F1	115.5 (5)	C18—C19A—H19D	108.4
C11—C10—C9	118.46 (19)	C20—C19A—H19D	108.4
F1—C10—C9	126.0 (5)	H19A—C19A—H19D	107.4
C11—C10—H10A	120.8	C18—C19A—H20C	148.5
C9—C10—H10A	120.8	H19A—C19A—H20C	97.1
O3—C11—C10	118.01 (19)	H19D—C19A—H20C	80.2
O3—C11—C12	119.54 (18)	C14—C19B—C20	115.7 (3)
C10—C11—C12	122.33 (18)	C14—C19B—H19B	108.4
C13—C12—C11	117.53 (18)	C20—C19B—H19B	108.4
C13—C12—C16	120.21 (18)	C14—C19B—H19C	108.4
C11—C12—C16	120.12 (17)	C20—C19B—H19C	108.4
O2—C13—C12	118.57 (17)	H19B—C19B—H19C	107.4
O2—C13—C8	119.35 (18)	C14—C19B—H20B	150.3
C12—C13—C8	121.95 (18)	H19B—C19B—H20B	84.4
C21A—C14—O2	111.8 (2)	H19C—C19B—H20B	92.3
C21A—C14—C19B	123.0 (3)	C15A—C20—C19A	115.7 (2)
O2—C14—C19B	124.8 (2)	C15B—C20—C19B	108.2 (2)
C21A—C14—C22A	114.9 (3)	C15A—C20—H20A	108.1
O2—C14—C22A	93.8 (2)	C15B—C20—H20A	125.7
O2—C14—C17B	98.7 (2)	C19A—C20—H20A	108.2
C19B—C14—C17B	110.6 (3)	C15A—C20—H20B	108.7
C22A—C14—C17B	167.0 (3)	C15B—C20—H20B	126.8
O2—C14—C23B	103.5 (2)	C19A—C20—H20B	108.5
C19B—C14—C23B	109.3 (3)	H20A—C20—H20B	107.5
C17B—C14—C23B	108.7 (3)	C15B—C20—H20C	110.3
C21A—C14—C15A	111.9 (3)	C19B—C20—H20C	110.2
O2—C14—C15A	112.16 (19)	H20A—C20—H20C	111.5
C22A—C14—C15A	111.1 (2)	C15A—C20—H20D	114.8
C23B—C14—C15A	143.8 (3)	C15B—C20—H20D	109.6
C20—C15A—C16	113.5 (3)	C19B—C20—H20D	110.0
C20—C15A—C14	117.8 (3)	H20B—C20—H20D	121.8
C16—C15A—C14	104.8 (2)	H20C—C20—H20D	108.5
C20—C15A—H15A	106.7	C14—C21A—H21A	109.5
C16—C15A—H15A	106.7	C14—C21A—H21B	109.5
C14—C15A—H15A	106.7	C14—C21A—H21C	109.5
C16—C15B—C20	108.9 (3)	C18—C21B—H21D	109.5
C16—C15B—C18	105.0 (2)	C18—C21B—H21E	109.5
C20—C15B—C18	111.0 (3)	H21D—C21B—H21E	109.5
C16—C15B—H15B	110.6	C18—C21B—H21F	109.5
C20—C15B—H15B	110.6	H21D—C21B—H21F	109.5
C18—C15B—H15B	110.6	H21E—C21B—H21F	109.5
C15B—C16—C12	105.9 (2)	C14—C22A—H22A	109.5
C12—C16—C15A	100.63 (19)	C14—C22A—H22B	109.5
C12—C16—C17A	109.7 (2)	C14—C22A—H22C	109.5
C15A—C16—C17A	110.6 (2)	C18—C22B—H22D	109.5
C15B—C16—C17B	111.2 (2)	C18—C22B—H22E	109.5
C12—C16—C17B	111.3 (2)	H22D—C22B—H22E	109.5
C17A—C16—C17B	138.9 (2)	C18—C22B—H22F	109.5
C15B—C16—H16A	142.2	H22D—C22B—H22F	109.5
C12—C16—H16A	111.8	H22E—C22B—H22F	109.5
C15A—C16—H16A	111.7	C18—C23A—H23A	109.5
C17A—C16—H16A	111.8	C18—C23A—H23B	109.5
C15B—C16—H16B	109.5	C18—C23A—H23C	109.5
C12—C16—H16B	109.4	C14—C23B—H23D	109.5
C15A—C16—H16B	149.7	C14—C23B—H23E	109.5
C17B—C16—H16B	109.5	H23D—C23B—H23E	109.5
C18—C17A—C16	109.3 (2)	C14—C23B—H23F	109.5
C18—C17A—H16B	138.2	H23D—C23B—H23F	109.5
C18—C17A—H17A	109.8	H23E—C23B—H23F	109.5
C16—C17A—H17A	109.8
C6—C1—C2—C3	−0.7 (3)	C11—C12—C16—C17B	171.5 (2)
C7—C1—C2—C3	−176.32 (17)	C20—C15A—C16—C15B	41.7 (3)
C1—C2—C3—C4	−1.4 (3)	C14—C15A—C16—C15B	171.6 (3)
C2—C3—C4—C5	1.4 (3)	C20—C15A—C16—C12	−60.4 (3)
C3—C4—C5—C6	0.6 (3)	C14—C15A—C16—C12	69.5 (2)
C4—C5—C6—C1	−2.7 (3)	C20—C15A—C16—C17A	55.5 (3)
C2—C1—C6—C5	2.7 (3)	C14—C15A—C16—C17A	−174.6 (2)
C7—C1—C6—C5	178.51 (17)	C20—C15A—C16—C17B	−169.0 (3)
C2—C1—C7—O1	130.05 (19)	C14—C15A—C16—C17B	−39.1 (2)
C6—C1—C7—O1	−45.6 (2)	C15B—C16—C17A—C18	−48.6 (3)
C2—C1—C7—C8	−47.5 (3)	C12—C16—C17A—C18	47.5 (3)
C6—C1—C7—C8	136.83 (18)	C15A—C16—C17A—C18	−62.6 (3)
O1—C7—C8—C9	−11.1 (3)	C17B—C16—C17A—C18	−132.0 (3)
C1—C7—C8—C9	166.34 (16)	C21A—C14—C17B—C16	−178.2 (3)
O1—C7—C8—C13	167.63 (17)	O2—C14—C17B—C16	71.8 (2)
C1—C7—C8—C13	−14.9 (3)	C19B—C14—C17B—C16	−60.6 (3)
C13—C8—C9—O4	−177.32 (15)	C22A—C14—C17B—C16	−93.0 (12)
C7—C8—C9—O4	1.5 (2)	C23B—C14—C17B—C16	179.4 (2)
C13—C8—C9—C10	0.0 (2)	C15A—C14—C17B—C16	−38.7 (2)
C7—C8—C9—C10	178.83 (16)	C15B—C16—C17B—C14	68.8 (3)
O4—C9—C10—C11	−179.84 (15)	C12—C16—C17B—C14	−49.0 (3)
C8—C9—C10—C11	2.8 (3)	C15A—C16—C17B—C14	41.7 (2)
O4—C9—C10—F1	0.4 (6)	C17A—C16—C17B—C14	130.6 (3)
C8—C9—C10—F1	−177.0 (6)	C16—C17A—C18—C22B	104.9 (7)
C18—O3—C11—C10	150.18 (17)	C16—C17A—C18—O3	−70.2 (3)
C18—O3—C11—C12	−25.9 (3)	C16—C17A—C18—C19A	53.5 (3)
F1—C10—C11—O3	8.6 (5)	C16—C17A—C18—C21B	−177.9 (3)
C9—C10—C11—O3	−171.17 (16)	C16—C17A—C18—C23A	−177.2 (2)
F1—C10—C11—C12	−175.5 (5)	C16—C17A—C18—C15B	42.9 (2)
C9—C10—C11—C12	4.8 (3)	C11—O3—C18—C17A	62.5 (2)
O3—C11—C12—C13	161.02 (16)	C11—O3—C18—C22B	−115.6 (3)
C10—C11—C12—C13	−14.9 (3)	C11—O3—C18—C19A	−61.9 (3)
O3—C11—C12—C16	−2.4 (3)	C11—O3—C18—C21B	125.1 (3)
C10—C11—C12—C16	−178.27 (16)	C11—O3—C18—C23A	−178.9 (2)
C14—O2—C13—C12	25.8 (3)	C11—O3—C18—C15B	5.5 (3)
C14—O2—C13—C8	−150.07 (18)	C16—C15B—C18—C17A	−45.8 (2)
C11—C12—C13—O2	−157.92 (17)	C20—C15B—C18—C17A	−163.4 (3)
C16—C12—C13—O2	5.5 (3)	C16—C15B—C18—C22B	155.0 (3)
C11—C12—C13—C8	17.8 (3)	C20—C15B—C18—C22B	37.5 (3)
C16—C12—C13—C8	−178.80 (16)	C16—C15B—C18—O3	40.1 (3)
C9—C8—C13—O2	165.09 (17)	C20—C15B—C18—O3	−77.4 (3)
C7—C8—C13—O2	−13.7 (3)	C16—C15B—C18—C19A	145.2 (3)
C9—C8—C13—C12	−10.6 (3)	C20—C15B—C18—C19A	27.6 (2)
C7—C8—C13—C12	170.64 (17)	C16—C15B—C18—C21B	−82.1 (3)
C13—O2—C14—C21A	−130.2 (3)	C20—C15B—C18—C21B	160.3 (3)
C13—O2—C14—C19B	57.1 (3)	C16—C15B—C18—C23A	−132.3 (4)
C13—O2—C14—C22A	111.0 (2)	C20—C15B—C18—C23A	110.1 (4)
C13—O2—C14—C17B	−65.6 (3)	C17A—C18—C19A—C20	−38.2 (4)
C13—O2—C14—C23B	−177.4 (3)	C22B—C18—C19A—C20	163.4 (4)
C13—O2—C14—C15A	−3.6 (3)	O3—C18—C19A—C20	78.0 (3)
C21A—C14—C15A—C20	−152.1 (3)	C21B—C18—C19A—C20	−111.2 (4)
O2—C14—C15A—C20	81.4 (3)	C23A—C18—C19A—C20	−170.3 (3)
C19B—C14—C15A—C20	−36.3 (3)	C15B—C18—C19A—C20	−28.1 (3)
C22A—C14—C15A—C20	−22.1 (4)	C21A—C14—C19B—C20	126.1 (4)
C17B—C14—C15A—C20	169.1 (3)	O2—C14—C19B—C20	−62.1 (4)
C23B—C14—C15A—C20	−108.9 (5)	C22A—C14—C19B—C20	−132.9 (4)
C21A—C14—C15A—C16	80.6 (3)	C17B—C14—C19B—C20	55.2 (4)
O2—C14—C15A—C16	−45.9 (3)	C23B—C14—C19B—C20	174.9 (3)
C19B—C14—C15A—C16	−163.6 (3)	C15A—C14—C19B—C20	31.6 (2)
C22A—C14—C15A—C16	−149.4 (2)	C16—C15A—C20—C15B	−39.4 (2)
C17B—C14—C15A—C16	41.8 (2)	C14—C15A—C20—C15B	−162.3 (4)
C23B—C14—C15A—C16	123.8 (5)	C16—C15A—C20—C19A	−39.4 (3)
C20—C15B—C16—C12	55.6 (3)	C14—C15A—C20—C19A	−162.4 (2)
C18—C15B—C16—C12	−63.4 (3)	C16—C15A—C20—C19B	155.8 (4)
C20—C15B—C16—C15A	−36.8 (2)	C14—C15A—C20—C19B	32.8 (3)
C18—C15B—C16—C15A	−155.8 (3)	C16—C15B—C20—C15A	38.8 (2)
C20—C15B—C16—C17A	158.9 (4)	C18—C15B—C20—C15A	153.9 (3)
C18—C15B—C16—C17A	40.0 (2)	C16—C15B—C20—C19A	−141.3 (3)
C20—C15B—C16—C17B	−65.5 (3)	C18—C15B—C20—C19A	−26.1 (2)
C18—C15B—C16—C17B	175.5 (2)	C16—C15B—C20—C19B	51.7 (3)
C13—C12—C16—C15B	−112.5 (2)	C18—C15B—C20—C19B	166.8 (2)
C11—C12—C16—C15B	50.5 (3)	C18—C19A—C20—C15A	29.5 (4)
C13—C12—C16—C15A	−54.6 (2)	C18—C19A—C20—C15B	29.5 (3)
C11—C12—C16—C15A	108.4 (2)	C18—C19A—C20—C19B	78.0 (8)
C13—C12—C16—C17A	−171.12 (19)	C14—C19B—C20—C15A	−35.2 (3)
C11—C12—C16—C17A	−8.2 (2)	C14—C19B—C20—C15B	−48.3 (4)
C13—C12—C16—C17B	8.6 (3)	C14—C19B—C20—C19A	−91.5 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O1	0.82	1.79	2.5211 (19)	148
C5—H5A···O1^i	0.93	2.43	3.333 (3)	163

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