A new estra-1,3,5(10)-triene-3,17[beta]-diol solvate: estradiol-methanol-water (3/2/1)

The title solvate of the steroid 17[beta]-estradiol (E₂) with methanol and water, C₁₈H₂₄O₂·0.67CH₄O·0.33H₂O, is the first E₂ derivative to contain three crystallographically independent mol­ecules in the asymmetric unit. The three steroid mol­ecules, along with two methanol mol­ecules and a water mol­ecule, create a three-dimensional hydrogen-bonded system. Three-sided columns are formed, with the estradiol mol­ecules aligned lengthwise parallel to (101), and joined by solvent mol­ecules at both hydro­philic ends. The three estradiol mol­ecules differ slightly in their ring-bowing angles, i.e. the angle between the mean plane of the A ring and that of the BCD ring; this angle ranges from 7.1 to 12.2°.

S1. Comment

17β-Estradiol, E₂, is a member of the estrogen family of hormones. In recent years, interest in these molecules has primarily focused on understanding their biological role in initiating breast cancer. It is well known that their ability to form hydrogen bonds in the active site of the estrogen receptor (ER) influences biological activity. This ability to form hydrogen bonds has been clearly demonstrated in an array of crystal structures, especially of E₂, containing different solvent molecules or other hydrogen-bond acceptors.

When comparing these structures, the flexibility of the hydrophobic region of the molecule, more specifically the B ring, becomes very apparent. Several papers have already discussed the ring bowing of this molecule (Cooper & Norton, 1969; Cody et al., 1971; Busetta et al., 1976; Duax et al., 1979). Weize & Brooks (1994) took it a step further, performing molecular-modeling calculations on observed and novel confirmations. Ivanov and coworkers carried out a related study which included a larger body of compounds and more detailed analysis (Ivanov et al., 1998). They concluded that there are two possible conformations very close in energy, which differ in the B-ring arrangement, although the chance of the strained-geometry binding is low, as one quarter of the binding energy (−11.9 kcal mol⁻¹; 1 kcal mol⁻¹ = 4.184 kJ mol⁻¹) is predicted to be lost (Anstead et al., 1997). The point initially postulated by Weize & Brooks remains, that the flexibility to allow bending or other conformational changes of the ligand in the receptor appears energetically achievable, and this could be an important property in determining their activity.

Molecular-dynamics studies on the ligand binding domain (LBD) of the ER demonstrate that the motion of the LBD requires the A ring to remain fairly steady while the CD ring retains a higher degree of freedom. The range of motion found in that study (Reference?) agrees very well with the reported crystal structures. It is well known that the hydrogen bonding of the ligand in the LBD causes conformational changes in the receptor. This seemingly accommodating motion of the LBD and the ligand supports the idea postulated by Weize & Brooks that the flexibility of E₂, or of any other ligand which enters the LBD, could also effect the activity of the ligand. A more rigid or flexible ligand could change the natural motion of the ER complex, resulting in a change in activation factor (AF-2) activity, and therefore possibly effecting coactivator recruitment. This process is not well understood; the flexibility of the ligand is certainly only one of many physical factors associated in the activity of E₂. The structure of the solvate reported here continues the trend in observing the flexibility of this molecule from a structural and hydrogen-bonding view, while the molecule lies in the lowest energy conformation.

The crystal of the title compound, (I), contains three crystallographically unique E₂ molecules (Fig. 1). The B rings of the E₂ molecules adopt the typical conformation of a distorted 7α,8β half chair, and this is responsible for most of the structural flexibility. Calculation of the ring-bowing angle, as defined by Duax & Norton (1975), reveals a range of 5.1° for the three molecules. Table 1 compares the ring-bowing angles of the known E₂ crystal structures. The spread of over 12°, with angles found distributed over the entire range, indicate the shallowness of the potential associated with the bowing deformation. In a system as dynamic as the human body, the molecule would certainly have a wide range of conformations easily available. \sch

The packing of (I) results in three-sided cylinders of estradiol molecules arranged parallel to (101), with the C18 methyl group pointing towards the center (Fig. 1). This, of course, aligns the large hydrophobic regions of the molecules, as well as the hydrophilic hydroxy groups. These cylinders then stack on top of each other, creating three-sided columns (Fig. 2) held together by hydrogen bonds involving the hydroxy groups and the three solvent molecules. A more detailed picture of the hydrogen bonding between the solvent and E₂ molecules can be seen in Fig. 3 and from Table 2. There is also an intercolumnar hydrogen bond, which occurs between the water molecule and a 3-hydroxy group. This, along with the intercolumnar hydrogen-bonded solvent, creates a hydrophilic layer which is approximately 30° from perpendicular to the columns (Fig. 4). Structurally, all bond lengths and angles are in expected ranges.

S2. Experimental

Crystals were grown by slow evaporation from a methanol solution open to the air. It is presumed that the methanol was either wet prior to use in this experiment or absorbed atmospheric moisture. Crystals of (I) were grown over the course of 3 d and harvested when reaching the appropriate size.

S3. Refinement

The absolute configuration of the E₂ molecules in (I) was known from the natural product starting material. The intensity data were corrected for decay and absorption using SADABS (Sheldrick, 1996). All H atoms on the solvent molecules and on the hydroxy groups of the E₂ molecules were located in the difference map and refined with isotropic displacement parameters. The remaining H atoms were included with idealized geometries, with C—H distances in the range 0.96–0.98 Å Is this added text OK?, and their isotropic displacement parameters were refined.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1994); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. A view of molecule A of (I), with the atom-numbering scheme; the other two molecules are similarly labeled, with the corresponding suffix B or C. Displacement ellipsoids are plotted at the 50% probability level. The solvent molecules have been omitted for clarity; the water molecule was labeled O3, while the O atoms of the methanol molecules A and B were labeled O4, with their C atoms labeled C19.
	Fig. 2. The molecular arrangement of (I), looking down the three-sided column. Displacement ellipsoids are plotted at the 50% probability level [symmetry codes: (i) x, y, z; (ii) −2 − x, y − 1/2, −1 − z; (iii) x − 1, y, z].
	Fig. 3. The packing of E2 groups in (I), with the hydrogen-bonded solvent molecules, viewed perpendicular to the columns. Dotted lines indicate the region detailed in Fig. 4. Displacement ellipsoids are plotted at the 50% probability level [symmetry codes: (i) x, y, z; (ii) 1 + x, y, 1 + z; (iii) −2 − x, y − 1/2, −1 − z; (iv) −1 − x, y − 1/2, −z; (v) x, y, 1 + z; (vi) −x, y − 1/2, −z].
	Fig. 4. The hydrogen-bonded region of the column shown in Fig. 3, including the solvent molecules and only the A or D rings of E2. Displacement ellipsoids are plotted at the 50% probability level [symmetry codes: (i) x, y, z; (ii) −x, y − 1/2, −z; (iii) −1 − x, y − 1/2, −z; (iv) 1 + x, y, 1 + z; (v) −2 − x, y − 1/2, −1 − z; (vi) x, y, 1 + z].
	Fig. 5. A schematic diagram of the packed columns in (I) and their relation to the hydrophilic layer containing the hydroxy groups and solvent molecules.

estra-1,3,5(10)-triene-3,17β-diol-methanol-water (3/2/1)

Crystal data

C18H24O2·0.67CH4O·0.33H2O	F(000) = 980
Mr = 299.74	Dx = 1.212 Mg m^−3
Monoclinic, P21	Ag Kα radiation, λ = 0.56085 Å
a = 11.7152 (4) Å	Cell parameters from 7309 reflections
b = 19.6270 (6) Å	θ = 2.3–27.9°
c = 12.1310 (4) Å	µ = 0.05 mm^−1
β = 117.978 (1)°	T = 298 K
V = 2463.34 (14) Å^3	Cuboid, colorless
Z = 6	0.4 × 0.3 × 0.3 mm

Data collection

Siemens SMART Platform CCD area-detector diffractometer	21122 independent reflections
Radiation source: fine-focus sealed tube	15597 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
ω scans	θmax = 27.9°, θmin = 1.5°
Absorption correction: empirical (using intensity measurements) multipole expansion (Blessing, 1995) using SADABS (Sheldrick, 1996)	h = −18→19
Tmin = 0.840, Tmax = 0.985	k = −32→29
44195 measured reflections	l = −20→20

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0812P)^2] where P = (Fo^2 + 2Fc^2)/3
21122 reflections	(Δ/σ)max = 0.001
698 parameters	Δρmax = 0.41 e Å^−3
1 restraint	Δρmin = −0.23 e Å^−3

Special details

Experimental. Preliminary examination and data collection were performed at 298 (1) K on a Siemens SMART Platform diffractometer equipped with a 2 K CCD detector located 6.12 cm from the crystal. 0.3° ω scans were carried out at three different ϕ settings and a detector position of −25° in 2θ, corresponding to a nominal sphere of data, with the frame time set at 30 s. The unit cell was initially refined with the SMART Software Package (Bruker, 1998). The final unit cell was obtained from the refinement of 7309 reflections after integration (SAINT 6; Bruker, 1999). The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 20 σ(I).

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
O1A	−0.58213 (11)	−0.44581 (7)	−0.24230 (11)	0.0243 (2)
H1OA	−0.564 (3)	−0.4213 (14)	−0.191 (2)	0.035 (7)*
O1B	−0.36786 (12)	−0.07606 (7)	−0.02309 (10)	0.0242 (2)
H1OB	−0.310 (3)	−0.0470 (16)	−0.011 (3)	0.060 (9)*
O1C	0.38139 (12)	−0.14101 (7)	0.19736 (10)	0.0252 (2)
H1OC	0.426 (2)	−0.1207 (13)	0.180 (2)	0.031 (6)*
C1A	−0.87445 (15)	−0.46604 (8)	−0.53895 (14)	0.0220 (3)
H1A	−0.9140	−0.4997	−0.5989	0.030 (6)*
C1B	−0.66131 (15)	−0.10511 (8)	−0.31570 (14)	0.0215 (3)
H1B	−0.7382	−0.1292	−0.3429	0.016 (4)*
C1C	0.10431 (16)	−0.11852 (8)	−0.11370 (14)	0.0211 (3)
H1C	0.0847	−0.0978	−0.1895	0.032 (6)*
O2A	−1.54143 (11)	−0.36438 (7)	−1.05600 (10)	0.0258 (2)
H2OA	−1.588 (2)	−0.3607 (12)	−1.028 (2)	0.031 (6)*
O2B	−1.16785 (11)	0.00670 (7)	−0.96783 (11)	0.0265 (2)
H2OB	−1.181 (2)	0.0430 (13)	−0.965 (2)	0.024 (6)*
O2C	−0.54233 (12)	−0.24553 (7)	−0.63644 (11)	0.0262 (2)
H2OC	−0.558 (2)	−0.2163 (13)	−0.679 (2)	0.028 (6)*
C2A	−0.75822 (16)	−0.48097 (8)	−0.43363 (14)	0.0228 (3)
H2A	−0.7215	−0.5240	−0.4232	0.025 (5)*
C2B	−0.57070 (16)	−0.10814 (8)	−0.19012 (14)	0.0227 (3)
H2B	−0.5871	−0.1338	−0.1347	0.039 (6)*
C2C	0.22891 (15)	−0.11229 (8)	−0.01588 (14)	0.0220 (3)
H2C	0.2909	−0.0873	−0.0259	0.034 (6)*
O3	0.55538 (14)	−0.07846 (8)	0.16279 (14)	0.0310 (3)
H3OA	0.562 (3)	−0.0433 (19)	0.182 (3)	0.064 (10)*
H3OB	0.572 (3)	−0.0802 (15)	0.109 (3)	0.044 (7)*
C3A	−0.69777 (14)	−0.43054 (8)	−0.34417 (13)	0.0194 (3)
C3B	−0.45539 (14)	−0.07245 (8)	−0.14829 (13)	0.0193 (3)
C3C	0.25995 (15)	−0.14399 (8)	0.09777 (13)	0.0201 (3)
C4A	−0.75440 (14)	−0.36653 (8)	−0.36054 (13)	0.0180 (2)
H4A	−0.7134	−0.3329	−0.3008	0.018 (5)*
C4B	−0.43123 (14)	−0.03468 (8)	−0.23238 (13)	0.0185 (2)
H4B	−0.3535	−0.0113	−0.2043	0.014 (4)*
C4C	0.16536 (15)	−0.17949 (8)	0.11182 (13)	0.0201 (3)
H4C	0.1860	−0.2000	0.1880	0.023 (5)*
O4A	−0.68702 (12)	−0.35029 (7)	−0.77190 (11)	0.0278 (2)
H4OA	−0.638 (3)	−0.3198 (15)	−0.726 (2)	0.042 (7)*
O4B	−1.74589 (11)	−0.35945 (6)	−1.01033 (11)	0.0253 (2)
H4OB	−1.732 (2)	−0.3502 (12)	−0.943 (2)	0.032 (6)*
C5A	−0.87205 (13)	−0.35197 (7)	−0.46537 (12)	0.0167 (2)
C5B	−0.52322 (14)	−0.03151 (7)	−0.35913 (13)	0.0171 (2)
C5C	0.03962 (14)	−0.18516 (8)	0.01380 (13)	0.0186 (2)
C6A	−0.93086 (15)	−0.28226 (8)	−0.47474 (13)	0.0206 (3)
H6A	−0.8625	−0.2485	−0.4446	0.024 (5)*
H6B	−0.9712	−0.2809	−0.4209	0.027 (5)*
C6B	−0.49137 (14)	0.01254 (8)	−0.44334 (13)	0.0205 (3)
H6C	−0.4035	0.0031	−0.4267	0.020 (5)*
H6D	−0.4955	0.0600	−0.4235	0.038 (6)*
C6C	−0.05782 (15)	−0.22562 (9)	0.03581 (13)	0.0223 (3)
H6E	−0.0497	−0.2134	0.1167	0.038 (6)*
H6F	−0.0379	−0.2737	0.0380	0.021 (5)*
C7A	−1.03110 (15)	−0.26353 (8)	−0.60694 (14)	0.0212 (3)
H7A	−0.9883	−0.2536	−0.6568	0.022 (5)*
H7B	−1.0775	−0.2230	−0.6050	0.035 (6)*
C7B	−0.58222 (14)	0.00116 (9)	−0.58210 (13)	0.0216 (3)
H7C	−0.5605	−0.0413	−0.6087	0.016 (4)*
H7D	−0.5720	0.0379	−0.6303	0.020 (5)*
C7C	−0.19687 (15)	−0.21376 (9)	−0.06365 (13)	0.0230 (3)
H7E	−0.2253	−0.1691	−0.0525	0.033 (6)*
H7F	−0.2528	−0.2476	−0.0555	0.029 (5)*
C8A	−1.12641 (13)	−0.32245 (7)	−0.66598 (12)	0.0157 (2)
H8A	−1.1645	−0.3340	−0.6117	0.013 (4)*
C8B	−0.72234 (13)	−0.00134 (8)	−0.60554 (12)	0.0174 (2)
H8B	−0.7396	0.0394	−0.5689	0.011 (4)*
C8C	−0.20613 (14)	−0.21864 (7)	−0.19346 (12)	0.0167 (2)
H8C	−0.1660	−0.2615	−0.1987	0.018 (5)*
C9A	−1.05536 (14)	−0.38532 (7)	−0.67877 (12)	0.0180 (2)
H9A	−1.0260	−0.3731	−0.7397	0.026 (5)*
C9B	−0.74143 (14)	−0.06525 (8)	−0.54097 (13)	0.0187 (2)
H9B	−0.7250	−0.1050	−0.5804	0.017 (4)*
C9C	−0.13013 (14)	−0.15915 (7)	−0.21100 (13)	0.0182 (2)
H9C	−0.1744	−0.1172	−0.2089	0.026 (5)*
C10A	−0.93396 (14)	−0.40215 (7)	−0.55787 (13)	0.0176 (2)
C10B	−0.64086 (14)	−0.06704 (7)	−0.40294 (13)	0.0179 (2)
C10C	0.00703 (14)	−0.15472 (7)	−0.10297 (13)	0.0181 (2)
C11A	−1.14894 (17)	−0.44601 (8)	−0.73560 (16)	0.0278 (3)
H11A	−1.1024	−0.4842	−0.7461	0.038 (6)*
H11B	−1.1812	−0.4598	−0.6785	0.037 (6)*
C11B	−0.88177 (14)	−0.07140 (9)	−0.56326 (14)	0.0221 (3)
H11D	−0.8992	−0.0348	−0.5196	0.023 (5)*
H11C	−0.8917	−0.1142	−0.5286	0.024 (5)*
C11C	−0.13627 (15)	−0.16209 (8)	−0.34092 (13)	0.0216 (3)
H11F	−0.0946	−0.1219	−0.3521	0.026 (5)*
H11E	−0.0888	−0.2017	−0.3449	0.020 (5)*
C12A	−1.26406 (16)	−0.42772 (9)	−0.86301 (15)	0.0258 (3)
H12B	−1.2331	−0.4200	−0.9234	0.032 (6)*
H12A	−1.3243	−0.4656	−0.8922	0.024 (5)*
C12B	−0.98135 (15)	−0.06837 (9)	−0.70274 (14)	0.0231 (3)
H12D	−0.9733	−0.1089	−0.7444	0.027 (5)*
H12C	−1.0679	−0.0676	−0.7112	0.039 (6)*
C12C	−0.27582 (15)	−0.16589 (8)	−0.44779 (14)	0.0220 (3)
H12F	−0.3199	−0.1234	−0.4521	0.025 (5)*
H12E	−0.2743	−0.1721	−0.5264	0.027 (5)*
C13A	−1.33352 (13)	−0.36405 (7)	−0.85340 (12)	0.0172 (2)
C13B	−0.96102 (14)	−0.00486 (8)	−0.76528 (13)	0.0184 (2)
C13C	−0.34993 (14)	−0.22482 (7)	−0.42817 (12)	0.0177 (2)
C14A	−1.23506 (14)	−0.30552 (7)	−0.79588 (13)	0.0177 (2)
H14A	−1.1939	−0.3001	−0.8495	0.024 (5)*
C14B	−0.82073 (14)	−0.00455 (8)	−0.74365 (12)	0.0181 (2)
H14B	−0.8073	−0.0484	−0.7745	0.023 (5)*
C14C	−0.34407 (14)	−0.21704 (8)	−0.29916 (13)	0.0184 (2)
H14C	−0.3777	−0.1715	−0.2978	0.024 (5)*
C15A	−1.31869 (16)	−0.24181 (8)	−0.81685 (15)	0.0260 (3)
H15A	−1.2746	−0.2013	−0.8229	0.041 (7)*
H15B	−1.3407	−0.2359	−0.7497	0.039 (6)*
C15B	−0.81885 (16)	0.04996 (9)	−0.83370 (14)	0.0246 (3)
H15C	−0.7528	0.0401	−0.8582	0.023 (5)*
H15D	−0.8032	0.0948	−0.7959	0.021 (5)*
C15C	−0.44498 (16)	−0.26782 (9)	−0.30191 (14)	0.0248 (3)
H15E	−0.4805	−0.2529	−0.2480	0.028 (5)*
H15F	−0.4076	−0.3128	−0.2758	0.031 (6)*
C16A	−1.44122 (16)	−0.25672 (9)	−0.94259 (15)	0.0262 (3)
H16A	−1.5186	−0.2534	−0.9328	0.039 (6)*
H16B	−1.4480	−0.2247	−1.0063	0.046 (7)*
C16B	−0.95591 (16)	0.04548 (9)	−0.94733 (14)	0.0258 (3)
H16C	−0.9976	0.0898	−0.9655	0.037 (6)*
H16D	−0.9511	0.0295	−1.0207	0.038 (6)*
C16C	−0.55067 (16)	−0.26816 (10)	−0.44117 (15)	0.0279 (3)
H16E	−0.5655	−0.3141	−0.4745	0.027 (5)*
H16F	−0.6314	−0.2500	−0.4496	0.027 (5)*
C17A	−1.42375 (14)	−0.32978 (8)	−0.97817 (13)	0.0205 (3)
H17A	−1.3755	−0.3263	−1.0256	0.018 (5)*
C17B	−1.03165 (14)	−0.00568 (8)	−0.90947 (13)	0.0223 (3)
H17B	−1.0190	−0.0510	−0.9359	0.034 (6)*
C17C	−0.49737 (15)	−0.22253 (8)	−0.51007 (13)	0.0213 (3)
H17C	−0.5273	−0.1757	−0.5117	0.022 (5)*
C18A	−1.40797 (16)	−0.37955 (9)	−0.78083 (14)	0.0248 (3)
H18C	−1.4675	−0.4162	−0.8207	0.037 (6)*
H18B	−1.4548	−0.3397	−0.7794	0.038 (6)*
H18A	−1.3482	−0.3924	−0.6969	0.026 (5)*
C18B	−0.99729 (15)	0.05956 (8)	−0.71729 (14)	0.0227 (3)
H18F	−0.9530	0.0597	−0.6277	0.019 (5)*
H18E	−1.0889	0.0602	−0.7464	0.043 (7)*
H18D	−0.9727	0.0991	−0.7478	0.034 (6)*
C18C	−0.29872 (16)	−0.29384 (8)	−0.44580 (14)	0.0231 (3)
H18I	−0.3047	−0.2957	−0.5274	0.042 (7)*
H18H	−0.3494	−0.3299	−0.4373	0.052 (8)*
H18G	−0.2101	−0.2990	−0.3837	0.037 (6)*
C19A	−0.78384 (17)	−0.36507 (10)	−0.73591 (17)	0.0311 (4)
H19A	−0.8396	−0.4003	−0.7887	0.044 (7)*
H19B	−0.8337	−0.3248	−0.7441	0.063 (9)*
H19C	−0.7436	−0.3801	−0.6507	0.028 (5)*
C19B	−1.81899 (17)	−0.30435 (9)	−1.08827 (16)	0.0282 (3)
H19G	−1.8379	−0.3134	−1.1729	0.031 (6)*
H19D	−1.7699	−0.2630	−1.0604	0.034 (6)*
H19E	−1.8983	−0.2995	−1.0839	0.045 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0197 (5)	0.0271 (6)	0.0183 (5)	0.0061 (4)	0.0025 (4)	−0.0009 (4)
O1B	0.0230 (5)	0.0288 (6)	0.0156 (4)	0.0007 (5)	0.0047 (4)	0.0011 (4)
O1C	0.0203 (5)	0.0309 (6)	0.0194 (5)	−0.0071 (5)	0.0051 (4)	0.0025 (4)
C1A	0.0218 (7)	0.0205 (7)	0.0199 (6)	0.0032 (5)	0.0066 (5)	−0.0038 (5)
C1B	0.0194 (6)	0.0212 (7)	0.0204 (6)	−0.0024 (5)	0.0065 (5)	0.0018 (5)
C1C	0.0237 (7)	0.0204 (7)	0.0187 (6)	−0.0029 (5)	0.0094 (5)	0.0028 (5)
O2A	0.0168 (5)	0.0391 (7)	0.0173 (5)	−0.0037 (5)	0.0045 (4)	−0.0053 (4)
O2B	0.0174 (5)	0.0276 (6)	0.0242 (5)	0.0015 (5)	0.0012 (4)	−0.0005 (4)
O2C	0.0285 (6)	0.0276 (6)	0.0157 (5)	−0.0019 (5)	0.0046 (4)	0.0017 (4)
C2A	0.0238 (7)	0.0210 (7)	0.0197 (6)	0.0064 (5)	0.0068 (5)	−0.0014 (5)
C2B	0.0224 (7)	0.0223 (7)	0.0211 (6)	0.0017 (6)	0.0084 (5)	0.0054 (5)
C2C	0.0224 (7)	0.0216 (7)	0.0214 (6)	−0.0045 (6)	0.0098 (5)	0.0013 (5)
O3	0.0372 (7)	0.0294 (7)	0.0327 (7)	−0.0120 (6)	0.0217 (6)	−0.0083 (5)
C3A	0.0180 (6)	0.0226 (7)	0.0163 (5)	0.0032 (5)	0.0069 (5)	0.0013 (5)
C3B	0.0205 (6)	0.0181 (6)	0.0166 (6)	0.0030 (5)	0.0065 (5)	0.0002 (5)
C3C	0.0205 (6)	0.0201 (7)	0.0185 (6)	−0.0035 (5)	0.0080 (5)	−0.0004 (5)
C4A	0.0152 (5)	0.0208 (6)	0.0163 (5)	0.0006 (5)	0.0059 (4)	−0.0006 (5)
C4B	0.0171 (6)	0.0197 (6)	0.0162 (5)	0.0002 (5)	0.0056 (5)	−0.0011 (5)
C4C	0.0218 (6)	0.0215 (7)	0.0173 (6)	−0.0023 (5)	0.0095 (5)	0.0009 (5)
O4A	0.0244 (6)	0.0361 (7)	0.0255 (5)	−0.0071 (5)	0.0139 (5)	−0.0048 (5)
O4B	0.0226 (5)	0.0290 (6)	0.0220 (5)	−0.0017 (5)	0.0084 (4)	−0.0023 (4)
C5A	0.0156 (6)	0.0183 (6)	0.0163 (5)	0.0010 (5)	0.0076 (5)	−0.0013 (4)
C5B	0.0170 (6)	0.0157 (6)	0.0171 (5)	0.0013 (5)	0.0068 (5)	−0.0003 (4)
C5C	0.0209 (6)	0.0191 (6)	0.0167 (6)	−0.0021 (5)	0.0095 (5)	0.0004 (5)
C6A	0.0186 (6)	0.0171 (6)	0.0190 (6)	0.0013 (5)	0.0029 (5)	−0.0033 (5)
C6B	0.0156 (6)	0.0254 (7)	0.0182 (6)	−0.0023 (5)	0.0061 (5)	0.0010 (5)
C6C	0.0216 (7)	0.0291 (8)	0.0163 (6)	−0.0053 (6)	0.0090 (5)	0.0020 (5)
C7A	0.0191 (6)	0.0153 (6)	0.0219 (6)	−0.0005 (5)	0.0037 (5)	0.0009 (5)
C7B	0.0166 (6)	0.0298 (7)	0.0166 (6)	−0.0005 (6)	0.0063 (5)	0.0010 (5)
C7C	0.0221 (7)	0.0322 (8)	0.0168 (6)	−0.0015 (6)	0.0110 (5)	0.0004 (5)
C8A	0.0152 (5)	0.0147 (6)	0.0153 (5)	−0.0002 (4)	0.0055 (4)	−0.0004 (4)
C8B	0.0151 (5)	0.0197 (6)	0.0157 (5)	−0.0001 (5)	0.0058 (4)	0.0001 (5)
C8C	0.0174 (6)	0.0178 (6)	0.0155 (5)	−0.0001 (5)	0.0083 (5)	0.0005 (4)
C9A	0.0165 (6)	0.0201 (6)	0.0146 (5)	0.0014 (5)	0.0051 (5)	−0.0017 (4)
C9B	0.0173 (6)	0.0186 (6)	0.0166 (5)	−0.0012 (5)	0.0050 (5)	−0.0010 (5)
C9C	0.0209 (6)	0.0169 (6)	0.0172 (5)	0.0002 (5)	0.0092 (5)	0.0010 (5)
C10A	0.0165 (6)	0.0184 (6)	0.0155 (5)	0.0012 (5)	0.0055 (5)	−0.0015 (4)
C10B	0.0177 (6)	0.0166 (6)	0.0173 (5)	0.0018 (5)	0.0066 (5)	0.0009 (5)
C10C	0.0205 (6)	0.0162 (6)	0.0172 (5)	−0.0016 (5)	0.0086 (5)	0.0001 (5)
C11A	0.0250 (7)	0.0185 (7)	0.0265 (7)	0.0025 (6)	0.0009 (6)	−0.0055 (6)
C11B	0.0167 (6)	0.0263 (7)	0.0195 (6)	−0.0029 (5)	0.0054 (5)	0.0030 (5)
C11C	0.0230 (7)	0.0257 (7)	0.0163 (6)	−0.0055 (6)	0.0093 (5)	0.0011 (5)
C12A	0.0214 (7)	0.0259 (7)	0.0220 (7)	0.0020 (6)	0.0034 (5)	−0.0088 (6)
C12B	0.0180 (6)	0.0253 (7)	0.0204 (6)	−0.0020 (6)	0.0044 (5)	0.0007 (5)
C12C	0.0247 (7)	0.0220 (7)	0.0181 (6)	−0.0012 (6)	0.0091 (5)	0.0040 (5)
C13A	0.0155 (5)	0.0194 (6)	0.0150 (5)	−0.0014 (5)	0.0059 (4)	−0.0013 (5)
C13B	0.0156 (5)	0.0203 (6)	0.0166 (5)	0.0004 (5)	0.0053 (5)	−0.0017 (5)
C13C	0.0179 (6)	0.0193 (6)	0.0151 (5)	0.0005 (5)	0.0071 (5)	0.0004 (5)
C14A	0.0165 (6)	0.0176 (6)	0.0170 (5)	−0.0018 (5)	0.0060 (5)	0.0006 (5)
C14B	0.0169 (6)	0.0210 (6)	0.0142 (5)	0.0019 (5)	0.0055 (4)	−0.0006 (5)
C14C	0.0189 (6)	0.0202 (6)	0.0169 (6)	0.0007 (5)	0.0091 (5)	0.0003 (5)
C15A	0.0204 (7)	0.0186 (7)	0.0265 (7)	0.0017 (6)	0.0006 (6)	0.0001 (5)
C15B	0.0213 (7)	0.0318 (8)	0.0185 (6)	0.0011 (6)	0.0075 (5)	0.0050 (6)
C15C	0.0217 (7)	0.0343 (8)	0.0180 (6)	−0.0055 (6)	0.0091 (5)	0.0015 (6)
C16A	0.0197 (7)	0.0250 (8)	0.0245 (7)	0.0024 (6)	0.0025 (5)	0.0032 (6)
C16B	0.0228 (7)	0.0341 (8)	0.0165 (6)	0.0037 (6)	0.0059 (5)	0.0030 (6)
C16C	0.0193 (7)	0.0388 (9)	0.0214 (7)	−0.0048 (6)	0.0062 (5)	0.0026 (6)
C17A	0.0164 (6)	0.0273 (7)	0.0154 (5)	−0.0013 (5)	0.0053 (5)	0.0013 (5)
C17B	0.0170 (6)	0.0255 (7)	0.0176 (6)	0.0028 (5)	0.0024 (5)	−0.0026 (5)
C17C	0.0183 (6)	0.0244 (7)	0.0175 (6)	0.0006 (5)	0.0054 (5)	0.0000 (5)
C18A	0.0223 (7)	0.0329 (8)	0.0192 (6)	−0.0073 (6)	0.0096 (5)	0.0004 (6)
C18B	0.0198 (6)	0.0247 (7)	0.0214 (6)	0.0042 (6)	0.0078 (5)	−0.0018 (5)
C18C	0.0252 (7)	0.0223 (7)	0.0207 (6)	0.0017 (6)	0.0099 (6)	−0.0034 (5)
C19A	0.0234 (7)	0.0372 (10)	0.0359 (8)	−0.0034 (7)	0.0165 (7)	0.0000 (7)
C19B	0.0254 (8)	0.0272 (8)	0.0295 (8)	0.0006 (6)	0.0109 (6)	−0.0053 (6)

Geometric parameters (Å, º)

O1A—C3A	1.3716 (18)	C9A—H9A	0.9800
O1A—H1OA	0.74 (3)	C9B—C10B	1.5305 (19)
O1B—C3B	1.3792 (17)	C9B—C11B	1.541 (2)
O1B—H1OB	0.85 (3)	C9B—H9B	0.9800
O1C—C3C	1.3691 (18)	C9C—C10C	1.527 (2)
O1C—H1OC	0.76 (3)	C9C—C11C	1.5447 (19)
C1A—C2A	1.393 (2)	C9C—H9C	0.9800
C1A—C10A	1.400 (2)	C11A—C12A	1.543 (2)
C1A—H1A	0.9300	C11A—H11A	0.9700
C1B—C2B	1.391 (2)	C11A—H11B	0.9700
C1B—C10B	1.405 (2)	C11B—C12B	1.541 (2)
C1B—H1B	0.9300	C11B—H11D	0.9700
C1C—C2C	1.389 (2)	C11B—H11C	0.9700
C1C—C10C	1.400 (2)	C11C—C12C	1.540 (2)
C1C—H1C	0.9300	C11C—H11F	0.9700
O2A—C17A	1.4254 (19)	C11C—H11E	0.9700
O2A—H2OA	0.76 (3)	C12A—C13A	1.525 (2)
O2B—C17B	1.4305 (19)	C12A—H12B	0.9700
O2B—H2OB	0.73 (2)	C12A—H12A	0.9700
O2C—C17C	1.4400 (19)	C12B—C13B	1.535 (2)
O2C—H2OC	0.73 (2)	C12B—H12D	0.9700
C2A—C3A	1.392 (2)	C12B—H12C	0.9700
C2A—H2A	0.9300	C12C—C13C	1.530 (2)
C2B—C3B	1.389 (2)	C12C—H12F	0.9700
C2B—H2B	0.9300	C12C—H12E	0.9700
C2C—C3C	1.396 (2)	C13A—C18A	1.533 (2)
C2C—H2C	0.9300	C13A—C17A	1.536 (2)
O3—H3OA	0.72 (4)	C13A—C14A	1.543 (2)
O3—H3OB	0.76 (3)	C13B—C18B	1.533 (2)
C3A—C4A	1.391 (2)	C13B—C14B	1.538 (2)
C3B—C4B	1.393 (2)	C13B—C17B	1.545 (2)
C3C—C4C	1.386 (2)	C13C—C18C	1.537 (2)
C4A—C5A	1.3979 (19)	C13C—C17C	1.537 (2)
C4A—H4A	0.9300	C13C—C14C	1.5416 (19)
C4B—C5B	1.4053 (19)	C14A—C15A	1.534 (2)
C4B—H4B	0.9300	C14A—H14A	0.9800
C4C—C5C	1.397 (2)	C14B—C15B	1.537 (2)
C4C—H4C	0.9300	C14B—H14B	0.9800
O4A—C19A	1.423 (2)	C14C—C15C	1.535 (2)
O4A—H4OA	0.83 (3)	C14C—H14C	0.9800
O4B—C19B	1.427 (2)	C15A—C16A	1.555 (2)
O4B—H4OB	0.78 (2)	C15A—H15A	0.9700
C5A—C10A	1.4112 (19)	C15A—H15B	0.9700
C5A—C6A	1.512 (2)	C15B—C16B	1.552 (2)
C5B—C10B	1.407 (2)	C15B—H15C	0.9700
C5B—C6B	1.513 (2)	C15B—H15D	0.9700
C5C—C10C	1.4149 (19)	C15C—C16C	1.557 (2)
C5C—C6C	1.514 (2)	C15C—H15E	0.9700
C6A—C7A	1.523 (2)	C15C—H15F	0.9700
C6A—H6A	0.9700	C16A—C17A	1.539 (2)
C6A—H6B	0.9700	C16A—H16A	0.9700
C6B—C7B	1.528 (2)	C16A—H16B	0.9700
C6B—H6C	0.9700	C16B—C17B	1.546 (2)
C6B—H6D	0.9700	C16B—H16C	0.9700
C6C—C7C	1.523 (2)	C16B—H16D	0.9700
C6C—H6E	0.9700	C16C—C17C	1.543 (2)
C6C—H6F	0.9700	C16C—H16E	0.9700
C7A—C8A	1.532 (2)	C16C—H16F	0.9700
C7A—H7A	0.9700	C17A—H17A	0.9800
C7A—H7B	0.9700	C17B—H17B	0.9800
C7B—C8B	1.530 (2)	C17C—H17C	0.9800
C7B—H7C	0.9700	C18A—H18C	0.9600
C7B—H7D	0.9700	C18A—H18B	0.9600
C7C—C8C	1.5299 (19)	C18A—H18A	0.9600
C7C—H7E	0.9700	C18B—H18F	0.9600
C7C—H7F	0.9700	C18B—H18E	0.9600
C8A—C14A	1.5270 (19)	C18B—H18D	0.9600
C8A—C9A	1.536 (2)	C18C—H18I	0.9600
C8A—H8A	0.9800	C18C—H18H	0.9600
C8B—C14B	1.5257 (18)	C18C—H18G	0.9600
C8B—C9B	1.550 (2)	C19A—H19A	0.9600
C8B—H8B	0.9800	C19A—H19B	0.9600
C8C—C14C	1.521 (2)	C19A—H19C	0.9600
C8C—C9C	1.542 (2)	C19B—H19G	0.9600
C8C—H8C	0.9800	C19B—H19D	0.9600
C9A—C10A	1.5251 (19)	C19B—H19E	0.9600
C9A—C11A	1.545 (2)
C3A—O1A—H1OA	113 (2)	H11D—C11B—H11C	107.8
C3B—O1B—H1OB	106 (2)	C12C—C11C—C9C	112.56 (12)
C3C—O1C—H1OC	110.3 (18)	C12C—C11C—H11F	109.1
C2A—C1A—C10A	122.41 (14)	C9C—C11C—H11F	109.1
C2A—C1A—H1A	118.8	C12C—C11C—H11E	109.1
C10A—C1A—H1A	118.8	C9C—C11C—H11E	109.1
C2B—C1B—C10B	122.39 (14)	H11F—C11C—H11E	107.8
C2B—C1B—H1B	118.8	C13A—C12A—C11A	111.17 (12)
C10B—C1B—H1B	118.8	C13A—C12A—H12B	109.4
C2C—C1C—C10C	122.72 (13)	C11A—C12A—H12B	109.4
C2C—C1C—H1C	118.6	C13A—C12A—H12A	109.4
C10C—C1C—H1C	118.6	C11A—C12A—H12A	109.4
C17A—O2A—H2OA	109.3 (18)	H12B—C12A—H12A	108.0
C17B—O2B—H2OB	110.2 (19)	C13B—C12B—C11B	111.16 (12)
C17C—O2C—H2OC	110.2 (19)	C13B—C12B—H12D	109.4
C3A—C2A—C1A	119.11 (14)	C11B—C12B—H12D	109.4
C3A—C2A—H2A	120.4	C13B—C12B—H12C	109.4
C1A—C2A—H2A	120.4	C11B—C12B—H12C	109.4
C3B—C2B—C1B	119.36 (14)	H12D—C12B—H12C	108.0
C3B—C2B—H2B	120.3	C13C—C12C—C11C	111.18 (12)
C1B—C2B—H2B	120.3	C13C—C12C—H12F	109.4
C1C—C2C—C3C	119.14 (14)	C11C—C12C—H12F	109.4
C1C—C2C—H2C	120.4	C13C—C12C—H12E	109.4
C3C—C2C—H2C	120.4	C11C—C12C—H12E	109.4
H3OA—O3—H3OB	107 (3)	H12F—C12C—H12E	108.0
O1A—C3A—C4A	121.96 (14)	C12A—C13A—C18A	110.43 (14)
O1A—C3A—C2A	118.25 (13)	C12A—C13A—C17A	115.38 (12)
C4A—C3A—C2A	119.79 (13)	C18A—C13A—C17A	109.81 (12)
O1B—C3B—C2B	118.01 (13)	C12A—C13A—C14A	109.39 (12)
O1B—C3B—C4B	122.15 (14)	C18A—C13A—C14A	113.21 (12)
C2B—C3B—C4B	119.84 (13)	C17A—C13A—C14A	98.19 (11)
O1C—C3C—C4C	118.22 (13)	C18B—C13B—C12B	110.32 (12)
O1C—C3C—C2C	122.26 (14)	C18B—C13B—C14B	113.36 (12)
C4C—C3C—C2C	119.52 (14)	C12B—C13B—C14B	108.67 (12)
C3A—C4A—C5A	121.01 (13)	C18B—C13B—C17B	109.99 (12)
C3A—C4A—H4A	119.5	C12B—C13B—C17B	115.23 (12)
C5A—C4A—H4A	119.5	C14B—C13B—C17B	98.92 (11)
C3B—C4B—C5B	120.65 (14)	C12C—C13C—C18C	110.95 (13)
C3B—C4B—H4B	119.7	C12C—C13C—C17C	115.14 (12)
C5B—C4B—H4B	119.7	C18C—C13C—C17C	109.24 (12)
C3C—C4C—C5C	121.33 (13)	C12C—C13C—C14C	108.95 (12)
C3C—C4C—H4C	119.3	C18C—C13C—C14C	113.22 (12)
C5C—C4C—H4C	119.3	C17C—C13C—C14C	98.90 (11)
C19A—O4A—H4OA	109.7 (19)	C8A—C14A—C15A	120.45 (12)
C19B—O4B—H4OB	106.5 (18)	C8A—C14A—C13A	112.89 (11)
C4A—C5A—C10A	120.02 (13)	C15A—C14A—C13A	104.35 (12)
C4A—C5A—C6A	118.25 (12)	C8A—C14A—H14A	106.1
C10A—C5A—C6A	121.71 (12)	C15A—C14A—H14A	106.1
C4B—C5B—C10B	120.24 (13)	C13A—C14A—H14A	106.1
C4B—C5B—C6B	117.31 (13)	C8B—C14B—C15B	119.77 (13)
C10B—C5B—C6B	122.43 (12)	C8B—C14B—C13B	112.57 (11)
C4C—C5C—C10C	120.00 (13)	C15B—C14B—C13B	104.60 (12)
C4C—C5C—C6C	118.22 (12)	C8B—C14B—H14B	106.4
C10C—C5C—C6C	121.77 (13)	C15B—C14B—H14B	106.4
C5A—C6A—C7A	113.37 (12)	C13B—C14B—H14B	106.4
C5A—C6A—H6A	108.9	C8C—C14C—C15C	120.53 (12)
C7A—C6A—H6A	108.9	C8C—C14C—C13C	112.18 (11)
C5A—C6A—H6B	108.9	C15C—C14C—C13C	104.28 (11)
C7A—C6A—H6B	108.9	C8C—C14C—H14C	106.3
H6A—C6A—H6B	107.7	C15C—C14C—H14C	106.3
C5B—C6B—C7B	113.29 (12)	C13C—C14C—H14C	106.3
C5B—C6B—H6C	108.9	C14A—C15A—C16A	103.48 (13)
C7B—C6B—H6C	108.9	C14A—C15A—H15A	111.1
C5B—C6B—H6D	108.9	C16A—C15A—H15A	111.1
C7B—C6B—H6D	108.9	C14A—C15A—H15B	111.1
H6C—C6B—H6D	107.7	C16A—C15A—H15B	111.1
C5C—C6C—C7C	113.26 (12)	H15A—C15A—H15B	109.0
C5C—C6C—H6E	108.9	C14B—C15B—C16B	103.77 (13)
C7C—C6C—H6E	108.9	C14B—C15B—H15C	111.0
C5C—C6C—H6F	108.9	C16B—C15B—H15C	111.0
C7C—C6C—H6F	108.9	C14B—C15B—H15D	111.0
H6E—C6C—H6F	107.7	C16B—C15B—H15D	111.0
C6A—C7A—C8A	110.06 (12)	H15C—C15B—H15D	109.0
C6A—C7A—H7A	109.6	C14C—C15C—C16C	103.81 (12)
C8A—C7A—H7A	109.6	C14C—C15C—H15E	111.0
C6A—C7A—H7B	109.6	C16C—C15C—H15E	111.0
C8A—C7A—H7B	109.6	C14C—C15C—H15F	111.0
H7A—C7A—H7B	108.2	C16C—C15C—H15F	111.0
C6B—C7B—C8B	109.97 (12)	H15E—C15C—H15F	109.0
C6B—C7B—H7C	109.7	C17A—C16A—C15A	105.51 (12)
C8B—C7B—H7C	109.7	C17A—C16A—H16A	110.6
C6B—C7B—H7D	109.7	C15A—C16A—H16A	110.6
C8B—C7B—H7D	109.7	C17A—C16A—H16B	110.6
H7C—C7B—H7D	108.2	C15A—C16A—H16B	110.6
C6C—C7C—C8C	109.81 (12)	H16A—C16A—H16B	108.8
C6C—C7C—H7E	109.7	C17B—C16B—C15B	105.77 (12)
C8C—C7C—H7E	109.7	C17B—C16B—H16C	110.6
C6C—C7C—H7F	109.7	C15B—C16B—H16C	110.6
C8C—C7C—H7F	109.7	C17B—C16B—H16D	110.6
H7E—C7C—H7F	108.2	C15B—C16B—H16D	110.6
C14A—C8A—C7A	112.96 (11)	H16C—C16B—H16D	108.7
C14A—C8A—C9A	107.42 (11)	C17C—C16C—C15C	105.51 (13)
C7A—C8A—C9A	110.06 (12)	C17C—C16C—H16E	110.6
C14A—C8A—H8A	108.8	C15C—C16C—H16E	110.6
C7A—C8A—H8A	108.8	C17C—C16C—H16F	110.6
C9A—C8A—H8A	108.8	C15C—C16C—H16F	110.6
C14B—C8B—C7B	113.42 (11)	H16E—C16C—H16F	108.8
C14B—C8B—C9B	107.93 (11)	O2A—C17A—C13A	116.67 (13)
C7B—C8B—C9B	109.19 (12)	O2A—C17A—C16A	114.53 (13)
C14B—C8B—H8B	108.7	C13A—C17A—C16A	104.62 (12)
C7B—C8B—H8B	108.7	O2A—C17A—H17A	106.8
C9B—C8B—H8B	108.7	C13A—C17A—H17A	106.8
C14C—C8C—C7C	113.63 (12)	C16A—C17A—H17A	106.8
C14C—C8C—C9C	108.78 (11)	O2B—C17B—C13B	116.05 (13)
C7C—C8C—C9C	109.14 (12)	O2B—C17B—C16B	113.90 (13)
C14C—C8C—H8C	108.4	C13B—C17B—C16B	104.62 (12)
C7C—C8C—H8C	108.4	O2B—C17B—H17B	107.3
C9C—C8C—H8C	108.4	C13B—C17B—H17B	107.3
C10A—C9A—C8A	112.45 (11)	C16B—C17B—H17B	107.3
C10A—C9A—C11A	114.11 (12)	O2C—C17C—C13C	114.70 (13)
C8A—C9A—C11A	111.08 (12)	O2C—C17C—C16C	110.85 (13)
C10A—C9A—H9A	106.2	C13C—C17C—C16C	104.51 (12)
C8A—C9A—H9A	106.2	O2C—C17C—H17C	108.9
C11A—C9A—H9A	106.2	C13C—C17C—H17C	108.9
C10B—C9B—C11B	113.62 (12)	C16C—C17C—H17C	108.9
C10B—C9B—C8B	110.61 (11)	C13A—C18A—H18C	109.5
C11B—C9B—C8B	111.71 (12)	C13A—C18A—H18B	109.5
C10B—C9B—H9B	106.8	H18C—C18A—H18B	109.5
C11B—C9B—H9B	106.8	C13A—C18A—H18A	109.5
C8B—C9B—H9B	106.8	H18C—C18A—H18A	109.5
C10C—C9C—C8C	111.59 (11)	H18B—C18A—H18A	109.5
C10C—C9C—C11C	113.85 (12)	C13B—C18B—H18F	109.5
C8C—C9C—C11C	111.03 (11)	C13B—C18B—H18E	109.5
C10C—C9C—H9C	106.6	H18F—C18B—H18E	109.5
C8C—C9C—H9C	106.6	C13B—C18B—H18D	109.5
C11C—C9C—H9C	106.6	H18F—C18B—H18D	109.5
C1A—C10A—C5A	117.64 (13)	H18E—C18B—H18D	109.5
C1A—C10A—C9A	121.31 (12)	C13C—C18C—H18I	109.5
C5A—C10A—C9A	120.87 (13)	C13C—C18C—H18H	109.5
C1B—C10B—C5B	117.52 (13)	H18I—C18C—H18H	109.5
C1B—C10B—C9B	121.37 (13)	C13C—C18C—H18G	109.5
C5B—C10B—C9B	121.11 (13)	H18I—C18C—H18G	109.5
C1C—C10C—C5C	117.28 (13)	H18H—C18C—H18G	109.5
C1C—C10C—C9C	121.60 (12)	O4A—C19A—H19A	109.5
C5C—C10C—C9C	121.08 (12)	O4A—C19A—H19B	109.5
C12A—C11A—C9A	111.80 (14)	H19A—C19A—H19B	109.5
C12A—C11A—H11A	109.3	O4A—C19A—H19C	109.5
C9A—C11A—H11A	109.3	H19A—C19A—H19C	109.5
C12A—C11A—H11B	109.3	H19B—C19A—H19C	109.5
C9A—C11A—H11B	109.3	O4B—C19B—H19G	109.5
H11A—C11A—H11B	107.9	O4B—C19B—H19D	109.5
C9B—C11B—C12B	112.68 (12)	H19G—C19B—H19D	109.5
C9B—C11B—H11D	109.1	O4B—C19B—H19E	109.5
C12B—C11B—H11D	109.1	H19G—C19B—H19E	109.5
C9B—C11B—H11C	109.1	H19D—C19B—H19E	109.5
C12B—C11B—H11C	109.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···O2A^i	0.74 (3)	1.89 (3)	2.6226 (17)	171 (3)
O1B—H1OB···O2B^i	0.85 (3)	1.83 (3)	2.6654 (18)	171 (3)
O1C—H1OC···O3	0.76 (3)	1.82 (3)	2.5767 (18)	170 (3)
O2A—H2OA···O4B	0.76 (3)	1.97 (3)	2.7017 (18)	162 (2)
O2B—H2OB···O4B^ii	0.73 (2)	2.06 (2)	2.7823 (19)	168 (2)
O2C—H2OC···O1C^iii	0.73 (2)	1.99 (3)	2.7169 (17)	175 (3)
O3—H3OA···O1A^iv	0.72 (4)	2.02 (4)	2.743 (2)	178 (4)
O3—H3OB···O1B^v	0.76 (3)	2.04 (3)	2.7926 (19)	173 (3)
O4A—H4OA···O2C	0.83 (3)	1.85 (3)	2.6809 (18)	174 (3)
O4B—H4OB···O4A^vi	0.78 (2)	1.88 (2)	2.6462 (17)	166 (2)

Symmetry codes: (i) x+1, y, z+1; (ii) −x−3, y+1/2, −z−2; (iii) x−1, y, z−1; (iv) −x, y+1/2, −z; (v) x+1, y, z; (vi) x−1, y, z.