6-[3-Hydroxy-17-oxoestra-1,3,5(10)-trien-7β-yl]­hexane­nitrile

In the title compound, C₂₄H₃₁NO₂, ring B adopts a conformation between the boat and twisted-boat forms. This conformation best accommodates adverse intramolecular H...H interactions between the H atoms of the 7β-substituent and the two nearest ring H atoms. The tilt angle between rings A and D is 28.6 (1)°.

S1. Comment

Recently, synthetic steroids have been proposed as radiodiagnostica (Katzenellenbogen, 1995; Melo e Silva et al., 2001; Wang et al., 2003), as well as potential drug delivery systems targeting oestrogen receptor positive breast cancer and other diseases associated with the oestrogen receptor ERα. Mandatory for the success of these compounds is a good binding affinity to the receptor. It has been determined that a C7 substituent, carrying a long chain with a polar terminus, often influences the binding affinity, where the commonly synthesized 7α-substituted oestrane-derived steroids have a much better binding affinity than the corresponding 7β-epimers. The authors have studied the binding affinity to the oestrogen receptor of C7-substituted oestra-1,3,5(10),6-tetraenes, i.e. compounds analogous to those described above, but with the C7 substituent branching off from an sp²-hybridized C atom (Inohae et al., 1999; Thiemann et al., 2002). It was deemed advantageous to prepare the 7β-substituted compounds in order to compare the binding affinity and in vivo biodistribution of a series of 7α- and 7β-substituted oestranes and of the corresponding 7-substituted oestra-1,3,5(10),6-tetraenes. The measurement of the X-ray crystal structure of the title compound, (I), was carried out in order to be able to better model the complex of a 7β-substituted steroidal ligand and the binding domain of the nuclear receptor, the X-ray crystal structure of which is known. \sch

The molecule of (I), with the atomic numbering scheme, is depicted in Fig. 1. Ring A shows a little distortion from planarity [average mean plane deviation 0.012 (2) Å], as is also evident in other oestrones and oestradiols for which X-ray structural analyses have been carried out. Ring C, with trans fusion to rings B and D, is fixed in a chair conformation. In oestra-1,3,5(10)-trienes, ring B, as a cyclohexen,e is known to be less rigid (Bucourt & Hainault, 1967). This is found in the three known polymorphs of oestrone [oestra-1,3,5(10)-trien-3-ol-17-one], where all three exhibit a slightly different conformation of ring B, although the α-H at C7 in each adopts an axial position (Busetta et al., 1973, and references cited therein). This situation holds true for derivatives of oestrone that are unsubstituted in ring B and for oestradiol [oestra-1,3,5(10)-trien-3,17β-diol], where both X-ray crystal structure analyses and calculations (Sebag et al., 2000) show that, again, the α-H at C7 (H6) takes an axial position.

The determining effect on the conformation of ring B in (I) is the 7β substituent, where potential interactions of the substituent with the C15α H atom (H14) and minor ones with the C5α and C5β H atoms (H5 and H4, respectively) force atom C7 and the C7β substituent upward, with a concomitant change in the C5—C7—C8—C9 dihedral angle to −18.2 (2)°. This compares with the range of −60.9 to −70.6° measured for different oestrane analogues of (I), such as for the polymorphs of oestrone, epioestradiol and oestradiol and as calculated for these molecules (Kubli-Garfias, 1998). Similarly, the C5—C5—C7—C8 dihedral angle here is −35.8 (2)°, compared with the range of 32.1–49.0° measured for the same oestrane analogues and as calculated (Kubli-Garfias, 1998). The C5—C5—C7—C19 dihedral angle is 88.8 (2)°; the equivalent C5—C5—C7—H7β dihedral angle in oestrone is 156.9 and 166.1° for the two crystal forms, respectively (Busetta et al., 1973). The intramolecular 1:4 contact distances H5···H6 (2.202 Å) and H4···H24 (2.169 Å) are short.

The conformation of ring B is between a boat and a twisted-boat conformation, as characterized by the Cremer & Pople (1975) puckering parameters, Q = 0.717 (3) Å, θ = 84.51 (21)° and ϕ = 227.8 (2)° [for a perfect boat conformation, θ = 90.0° and ϕ = k × 60°; for a perfect twisted-boat conformation, θ = 90.0° and ϕ = k × 60° + 30° (Boeyens, 1978)]. This is also in accordance with the relative signs of the endocyclic torsion angles within ring B [see Boeyens (1978)]. In contrast with most other oestrane derivatives, neither the α-H atom at C7 (H6) nor the β-H atom at C5 (H4) adopts an axial position. Importantly, this different conformation of ring B leads to a much larger tilt angle between ring D and the phenolic ring A than is known for oestra-1,3,5(10)-trienes; for (I), the angle between the two mean planes defined by the C atoms of rings A and D is 28.6 (1)°.

The C5—C7, C7—C8 and C8—C9 bond lengths in (I) (Table 1) are significantly longer than those reported for non-substituted oestrones (Busetta et al., 1973; Hejaz et al., 1999). The C5—C5 and C9—C10 bond lengths have comparable values or are a little shorter. In the crystal of (I), the C7 substituent lies above the mean plane defined by the steroidal skeleton (rings A, B, C and D, averaged over all 17 atoms of the framework), with a calculated distance from the plane of 3.862 Å for atom C24 and 3.798 Å for atom N1. The chiral centres at C7, C8, C9, C13 and C14 are S, R, S, S and S, respectively.

In the crystal, compound (I) packs as molecular chains along the b axis, bound by a strong O1—H21···N1ⁱ hydrogen bond [O1···N1ⁱ 2.894 (3) Å, H21···N1ⁱ 2.074 Å, O1—H21···N1ⁱ 177°; symmetry code: (i) x, y − 1, z] and a weaker C23—H31···O2ⁱⁱ interaction [C23···O2ⁱⁱ 3.165 (3) Å, H31···O2ⁱⁱ 2.392 Å, C23—H31···O2ⁱⁱ 138.2 Å; symmetry code: (ii) −x, 1/2 + y, −z], as shown in Fig. 2.

S2. Experimental

Compound (I) was prepared by hydrogenolysis of 3-o-benzyl-7-(5'-cyanopentyl)oestra-1,3,5(10),6-tetraen-3-ol-17-one (Pd/C, H₂, MeOH; Thiemann et al., 2003). 3-o-Benzyl-7α-(5'-cyanopentyl)oestra-1,3,5(10),6-tetraen-3-ol-17-one was prepared from 3-o-benzyloestra-1,3,5(10),6-trien-3-ol-6,17-dione 17,17-[2''-(5'',5''-dimethyl-1'',3''-dioxane)] by a procedure analogous to that described for 3-o-methyloestra-1,3,5(10),6-trien-3-ol-6,17-dione 17,17-[2''-(5'',5''-dimethyl-1'',3''-dioxane)] (Inohae et al., 1999; Thiemann et al., 2002). The crystal used for the present X-ray structure analysis was obtained by recrystallization of (I) from dichloromethane/hexane (Ratio?).

S3. Refinement

The structure was solved by direct methods (Altomare et al., 1999) and expanded using Fourier techniques (Beurskens et al., 1999). The positional parameters of the H atoms were calculated geometrically (C—H = 0.95 and O—H = 0.82 Å) and refined using a riding model, with U_iso(H) set to 1.2U_eq(O, C). For geometric calculations, the program DIHED (Hitzer, Year?) was used. The ring-puckering analysis was carried out using PLATON (Spek, 2003).

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkins et al., 1996); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: CrystalStructure.

Figures

	Fig. 1. A view of the molecule of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A view of the unit cell of (I) down the a axis, showing the intermolecular contacts.

(I)

Crystal data

C24H31NO2	F(000) = 396.00
Mr = 365.51	Dx = 1.188 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2yb	Cell parameters from 9657 reflections
a = 6.639 (3) Å	θ = 3.0–27.5°
b = 13.530 (6) Å	µ = 0.07 mm^−1
c = 11.910 (5) Å	T = 293 K
β = 107.25 (3)°	Needle, colourless
V = 1021.7 (7) Å^3	0.50 × 0.20 × 0.12 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID diffractometer	2082 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.034
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
Tmin = 0.982, Tmax = 0.991	k = −17→17
20270 measured reflections	l = −15→15
2458 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0003Fo^2 + 1.0σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.035	(Δ/σ)max < 0.001
wR(F^2) = 0.082	Δρmax = 0.29 e Å^−3
S = 1.04	Δρmin = −0.25 e Å^−3
2441 reflections	Extinction correction: Eq. 22 in Larson (1970)
276 parameters	Extinction coefficient: 885 (45)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
O1	0.0856 (3)	−0.0530 (1)	0.4775 (1)	0.0254 (4)
O2	1.0587 (3)	0.1716 (1)	−0.0532 (2)	0.0322 (5)
N1	−0.1085 (3)	0.7612 (2)	0.3835 (2)	0.0295 (6)
C1	0.4635 (3)	−0.0668 (2)	0.3051 (2)	0.0187 (5)
C2	0.3111 (4)	−0.0966 (2)	0.3576 (2)	0.0201 (5)
C3	0.2352 (4)	−0.0295 (2)	0.4236 (2)	0.0207 (6)
C4	0.3151 (4)	0.0668 (2)	0.4388 (2)	0.0203 (5)
C5	0.4695 (4)	0.0953 (2)	0.3880 (2)	0.0188 (5)
C6	0.5692 (4)	0.1961 (2)	0.4059 (2)	0.0199 (5)
C7	0.5667 (3)	0.2455 (2)	0.2887 (2)	0.0170 (5)
C8	0.5994 (3)	0.1691 (2)	0.1980 (2)	0.0159 (5)
C9	0.6963 (3)	0.0705 (2)	0.2588 (2)	0.0179 (5)
C10	0.5425 (3)	0.0290 (2)	0.3187 (2)	0.0185 (5)
C11	0.7547 (4)	−0.0021 (2)	0.1745 (2)	0.0213 (5)
C12	0.8957 (4)	0.0444 (2)	0.1079 (2)	0.0219 (6)
C13	0.7868 (3)	0.1351 (2)	0.0419 (2)	0.0188 (5)
C14	0.7411 (3)	0.2100 (2)	0.1288 (2)	0.0171 (5)
C15	0.6826 (4)	0.3056 (2)	0.0558 (2)	0.0217 (6)
C16	0.8446 (4)	0.3060 (2)	−0.0146 (2)	0.0245 (6)
C17	0.9178 (4)	0.1991 (2)	−0.0156 (2)	0.0224 (6)
C18	0.5877 (4)	0.1071 (2)	−0.0592 (2)	0.0256 (6)
C19	0.3624 (3)	0.3041 (2)	0.2387 (2)	0.0182 (5)
C20	0.3538 (4)	0.4002 (2)	0.3049 (2)	0.0207 (5)
C21	0.1369 (3)	0.4485 (2)	0.2671 (2)	0.0196 (5)
C22	0.1294 (3)	0.5462 (2)	0.3290 (2)	0.0185 (5)
C23	−0.0973 (3)	0.5869 (2)	0.2936 (2)	0.0191 (5)
C24	−0.1077 (4)	0.6850 (2)	0.3428 (2)	0.0208 (5)
H1	0.5139	−0.1127	0.2594	0.022 (1)*
H2	0.2593	−0.1624	0.3484	0.023 (1)*
H3	0.2644	0.1129	0.4842	0.024 (1)*
H4	0.4928	0.2368	0.4439	0.023 (1)*
H5	0.7110	0.1902	0.4542	0.023 (1)*
H6	0.6808	0.2910	0.3049	0.020 (1)*
H7	0.4656	0.1546	0.1439	0.018 (1)*
H8	0.8221	0.0866	0.3189	0.021 (1)*
H9	0.8278	−0.0565	0.2188	0.026 (1)*
H10	0.6287	−0.0250	0.1192	0.026 (1)*
H11	1.0267	0.0634	0.1617	0.026 (1)*
H12	0.9198	−0.0022	0.0536	0.026 (1)*
H13	0.8731	0.2230	0.1853	0.020 (1)*
H14	0.6984	0.3622	0.1049	0.026 (1)*
H15	0.5421	0.3027	0.0050	0.026 (1)*
H16	0.9606	0.3476	0.0223	0.029 (1)*
H17	0.7802	0.3282	−0.0927	0.029 (1)*
H18	0.4977	0.0670	−0.0295	0.030 (1)*
H19	0.5155	0.1659	−0.0918	0.031 (1)*
H20	0.6271	0.0719	−0.1185	0.031 (1)*
H21	0.0314	−0.1064	0.4534	0.032 (1)*
H22	0.2473	0.2634	0.2415	0.022 (1)*
H23	0.3493	0.3206	0.1593	0.022 (1)*
H24	0.3887	0.3853	0.3864	0.025 (1)*
H25	0.4542	0.4454	0.2919	0.025 (1)*
H26	0.0382	0.4048	0.2845	0.023 (1)*
H27	0.0985	0.4596	0.1847	0.023 (1)*
H28	0.1774	0.5369	0.4117	0.022 (1)*
H29	0.2180	0.5925	0.3066	0.022 (1)*
H30	−0.1830	0.5428	0.3216	0.023 (1)*
H31	−0.1487	0.5906	0.2103	0.023 (1)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0302 (9)	0.0229 (9)	0.0267 (8)	−0.0049 (7)	0.0141 (7)	−0.0033 (7)
O2	0.0308 (9)	0.039 (1)	0.0328 (9)	−0.0012 (8)	0.0189 (8)	−0.0046 (8)
N1	0.026 (1)	0.022 (1)	0.043 (1)	0.0027 (9)	0.0138 (9)	0.001 (1)
C1	0.019 (1)	0.017 (1)	0.019 (1)	0.0031 (8)	0.0043 (8)	−0.0027 (9)
C2	0.023 (1)	0.016 (1)	0.020 (1)	−0.0011 (9)	0.0036 (9)	0.0000 (9)
C3	0.021 (1)	0.024 (1)	0.016 (1)	0.0012 (9)	0.0041 (9)	0.0026 (9)
C4	0.024 (1)	0.021 (1)	0.015 (1)	0.0025 (9)	0.0054 (8)	−0.0016 (9)
C5	0.019 (1)	0.017 (1)	0.016 (1)	0.0007 (9)	0.0001 (8)	0.0012 (9)
C6	0.024 (1)	0.018 (1)	0.018 (1)	−0.0003 (9)	0.0049 (9)	−0.0026 (9)
C7	0.016 (1)	0.016 (1)	0.018 (1)	−0.0009 (8)	0.0043 (8)	−0.0033 (9)
C8	0.0146 (9)	0.016 (1)	0.0159 (9)	0.0014 (8)	0.0028 (8)	−0.0014 (8)
C9	0.0154 (9)	0.018 (1)	0.019 (1)	0.0014 (8)	0.0034 (8)	0.0008 (9)
C10	0.017 (1)	0.020 (1)	0.016 (1)	0.0018 (9)	0.0006 (8)	0.0010 (8)
C11	0.022 (1)	0.016 (1)	0.026 (1)	0.0032 (9)	0.0079 (9)	−0.0013 (9)
C12	0.021 (1)	0.020 (1)	0.025 (1)	0.0028 (9)	0.0086 (9)	−0.0037 (9)
C13	0.017 (1)	0.022 (1)	0.019 (1)	−0.0003 (9)	0.0064 (8)	−0.0039 (9)
C14	0.0146 (9)	0.018 (1)	0.018 (1)	−0.0006 (8)	0.0036 (8)	−0.0023 (9)
C15	0.023 (1)	0.020 (1)	0.022 (1)	0.0003 (9)	0.0061 (9)	0.0014 (9)
C16	0.025 (1)	0.028 (1)	0.020 (1)	−0.002 (1)	0.0063 (9)	0.003 (1)
C17	0.021 (1)	0.030 (1)	0.015 (1)	−0.004 (1)	0.0030 (8)	−0.0017 (9)
C18	0.023 (1)	0.032 (1)	0.022 (1)	−0.002 (1)	0.0054 (9)	−0.006 (1)
C19	0.018 (1)	0.019 (1)	0.018 (1)	0.0018 (9)	0.0053 (8)	−0.0021 (9)
C20	0.020 (1)	0.020 (1)	0.023 (1)	0.0020 (9)	0.0060 (9)	−0.0024 (9)
C21	0.018 (1)	0.020 (1)	0.020 (1)	0.0002 (9)	0.0045 (9)	−0.0028 (9)
C22	0.018 (1)	0.017 (1)	0.021 (1)	0.0019 (9)	0.0060 (8)	−0.0014 (8)
C23	0.018 (1)	0.018 (1)	0.021 (1)	0.0019 (8)	0.0058 (8)	0.0003 (9)
C24	0.017 (1)	0.022 (1)	0.025 (1)	0.0021 (9)	0.0088 (9)	0.006 (1)

Geometric parameters (Å, º)

O1—C3	1.371 (3)	C12—H12	0.950
O1—H21	0.820	C13—C14	1.542 (3)
O2—C17	1.209 (3)	C13—C17	1.526 (4)
N1—C24	1.141 (3)	C13—C18	1.548 (3)
C1—C2	1.396 (4)	C14—C15	1.542 (3)
C1—C10	1.390 (3)	C14—H13	0.950
C1—H1	0.950	C15—C16	1.548 (4)
C2—C3	1.389 (4)	C15—H14	0.950
C2—H2	0.950	C15—H15	0.950
C3—C4	1.398 (3)	C16—C17	1.527 (4)
C4—C5	1.391 (4)	C16—H16	0.950
C4—H3	0.950	C16—H17	0.950
C5—C6	1.503 (3)	C18—H18	0.950
C5—C10	1.399 (3)	C18—H19	0.950
C6—C7	1.543 (3)	C18—H20	0.950
C6—H4	0.950	C19—C20	1.531 (3)
C6—H5	0.950	C19—H22	0.950
C7—C8	1.557 (3)	C19—H23	0.950
C7—C19	1.530 (3)	C20—C21	1.523 (3)
C7—H6	0.950	C20—H24	0.950
C8—C9	1.562 (3)	C20—H25	0.950
C8—C14	1.527 (3)	C21—C22	1.521 (3)
C8—H7	0.950	C21—H26	0.950
C9—C10	1.516 (4)	C21—H27	0.950
C9—C11	1.534 (3)	C22—C23	1.539 (3)
C9—H8	0.950	C22—H28	0.950
C11—C12	1.531 (4)	C22—H29	0.950
C11—H9	0.950	C23—C24	1.461 (3)
C11—H10	0.950	C23—H30	0.950
C12—C13	1.519 (3)	C23—H31	0.950
C12—H11	0.950
O1···N1^i	2.894 (3)	C18···H17	3.324
O1···C2	2.429 (3)	C18···H25^iii	3.476
O1···C4	2.362 (3)	C18···H27^iii	3.521
O1···C9^ii	3.503 (2)	C18···H29^iii	3.554
O1···H2	2.634	C18···H30^xi	3.572
O1···H3	2.529	C18···H31^xi	2.945
O1···H8^ii	2.871	C19···C5	3.300 (3)
O1···H9^ii	3.05	C19···C6	2.522 (3)
O2···C12	3.007 (3)	C19···C8	2.550 (3)
O2···C13	2.449 (3)	C19···C14	3.407 (3)
O2···C14	3.482 (3)	C19···C15	3.466 (4)
O2···C16	2.434 (3)	C19···C21	2.545 (3)
O2···C18	3.227 (3)	C19···H4	2.509
O2···C22^iii	3.576 (3)	C19···H5	3.285
O2···C23^iii	3.165 (3)	C19···H6	2.033
O2···C24^iii	3.564 (3)	C19···H7	2.508
O2···H7^iv	3.017	C19···H13^ii	3.307
O2···H11	3.01	C19···H14	3.201
O2···H12	2.948	C19···H15	3.338
O2···H13	3.485	C19···H16^ii	3.167
O2···H15^iv	3.551	C19···H24	2.037
O2···H16	2.692	C19···H25	2.049
O2···H17	2.759	C19···H26	2.736
O2···H18^iv	3.177	C19···H27	2.692
O2···H19	3.498	C20···C6	3.177 (3)
O2···H19^iv	3.201	C20···C7	2.565 (3)
O2···H20	3.052	C20···C22	2.541 (3)
O2···H22^iv	3.581	C20···H4	2.752
O2···H23^iv	3.361	C20···H6	2.626
O2···H27^iii	3.286	C20···H20^ix	3.242
O2···H29^iii	3.216	C20···H22	2.044
O2···H31^iii	2.392	C20···H23	2.034
N1···O1^v	2.894 (3)	C20···H26	2.038
N1···C1^vi	3.576 (3)	C20···H27	2.032
N1···C2^v	3.474 (3)	C20···H28	2.7
N1···C3^v	3.578 (3)	C20···H29	2.755
N1···C22	3.463 (3)	C20···H30^iv	3.586
N1···C23	2.601 (3)	C21···C19	2.545 (3)
N1···H1^vi	3.03	C21···C23	2.512 (3)
N1···H2^v	2.795	C21···H13^ii	3.509
N1···H9^vi	3.102	C21···H14^ii	3.199
N1···H21^v	2.074	C21···H16^ii	3.116
N1···H28	3.543	C21···H20^ix	3.166
N1···H29	3.454	C21···H22	2.652
N1···H30	3.051	C21···H23	2.776
N1···H31	3.055	C21···H24	2.034
C1···N1^vii	3.576 (3)	C21···H25	2.039
C1···C3	2.411 (4)	C21···H28	2.047
C1···C4	2.775 (3)	C21···H29	2.038
C1···C5	2.401 (3)	C21···H30	2.716
C1···C9	2.579 (3)	C21···H31	2.643
C1···C11	2.951 (4)	C22···O2^ix	3.576 (3)
C1···H2	2.047	C22···N1	3.463 (3)
C1···H7	3.561	C22···C20	2.541 (3)
C1···H8	3.126	C22···C24	2.487 (3)
C1···H9	2.899	C22···H20^ix	3.38
C1···H10	2.805	C22···H24	2.734
C1···H11^ii	3.39	C22···H25	2.697
C1···H17^iii	2.934	C22···H26	2.029
C2···O1	2.429 (3)	C22···H27	2.039
C2···N1^i	3.474 (3)	C22···H30	2.05
C2···C4	2.409 (3)	C22···H31	2.054
C2···C5	2.784 (3)	C23···O2^ix	3.165 (3)
C2···C10	2.425 (3)	C23···N1	2.601 (3)
C2···H1	2.04	C23···C21	2.512 (3)
C2···H3	3.268	C23···H18^xii	3.475
C2···H9^ii	3.19	C23···H19^xii	3.267
C2···H11^ii	3.329	C23···H20^xii	3.523
C2···H17^iii	3.197	C23···H25^ii	3.535
C2···H21	2.455	C23···H26	2.636
C3···N1^i	3.578 (3)	C23···H27	2.708
C3···C1	2.411 (4)	C23···H28	2.059
C3···C5	2.418 (3)	C23···H29	2.055
C3···C10	2.804 (4)	C24···O2^ix	3.564 (3)
C3···H1	3.265	C24···C22	2.487 (3)
C3···H2	2.036	C24···H2^v	3.179
C3···H3	2.046	C24···H19^xii	3.397
C3···H8^ii	3.085	C24···H21^v	3.135
C3···H9^ii	3.08	C24···H28	2.711
C3···H11^ii	3.266	C24···H29	2.643
C3···H21	1.823	C24···H30	1.985
C4···O1	2.362 (3)	C24···H31	1.985
C4···C1	2.775 (3)	H1···N1^vii	3.03
C4···C2	2.409 (3)	H1···C2	2.04
C4···C6	2.541 (3)	H1···C3	3.265
C4···C10	2.422 (4)	H1···C5	3.259
C4···H2	3.267	H1···C9	2.759
C4···H4	2.578	H1···C10	2.032
C4···H5	3.073	H1···C11	2.602
C4···H8^ii	3.171	H1···C16^iii	3.355
C4···H11^ii	3.288	H2···O1	2.634
C4···H21	3.044	H2···N1^i	2.795
C4···H22	3.49	H2···C1	2.047
C5···C1	2.401 (3)	H2···C3	2.036
C5···C2	2.784 (3)	H2···C4	3.267
C5···C3	2.418 (3)	H2···C10	3.281
C5···C7	2.529 (3)	H2···C24^i	3.179
C5···C8	2.832 (3)	H3···O1	2.529
C5···C9	2.475 (4)	H3···C2	3.268
C5···C19	3.300 (3)	H3···C3	2.046
C5···H1	3.259	H3···C5	2.037
C5···H3	2.037	H3···C6	2.712
C5···H4	2.018	H3···C10	3.277
C5···H5	2.022	H4···C4	2.578
C5···H6	3.283	H4···C5	2.018
C5···H7	3.008	H4···C7	2.052
C5···H8	2.705	H4···C8	3.34
C5···H11^ii	3.376	H4···C10	3.245
C5···H22	2.978	H4···C19	2.509
C6···C4	2.541 (3)	H4···C20	2.752
C6···C7	1.543 (3)	H5···C4	3.073
C6···C8	2.569 (3)	H5···C5	2.022
C6···C9	2.748 (3)	H5···C7	2.06
C6···C10	2.473 (3)	H5···C8	2.933
C6···C19	2.522 (3)	H5···C9	2.814
C6···C20	3.177 (3)	H5···C10	2.747
C6···H3	2.712	H5···C19	3.285
C6···H6	2.042	H6···C5	3.283
C6···H7	3.041	H6···C6	2.042
C6···H8	2.669	H6···C8	2.056
C6···H22	2.598	H6···C9	3.04
C6···H23	3.324	H6···C14	2.501
C6···H24	2.806	H6···C15	2.976
C7···C5	2.529 (3)	H6···C19	2.033
C7···C6	1.543 (3)	H6···C20	2.626
C7···C8	1.557 (3)	H7···O2^ii	3.017
C7···C9	2.580 (3)	H7···C1	3.561
C7···C10	2.961 (3)	H7···C5	3.008
C7···C14	2.551 (4)	H7···C6	3.041
C7···C15	3.196 (4)	H7···C7	2.061
C7···C20	2.565 (3)	H7···C9	2.067
C7···H4	2.052	H7···C10	2.617
C7···H5	2.06	H7···C11	2.811
C7···H7	2.061	H7···C12	3.36
C7···H8	2.695	H7···C13	2.763
C7···H13	2.69	H7···C14	2.034
C7···H14	3.031	H7···C15	2.871
C7···H15	3.423	H7···C18	2.844
C7···H22	2.04	H7···C19	2.508
C7···H23	2.042	H8···O1^iv	2.871
C7···H24	2.672	H8···C1	3.126
C7···H25	2.809	H8···C3^iv	3.085
C8···C5	2.832 (3)	H8···C4^iv	3.171
C8···C6	2.569 (3)	H8···C5	2.705
C8···C7	1.557 (3)	H8···C6	2.669
C8···C9	1.562 (3)	H8···C7	2.695
C8···C10	2.474 (3)	H8···C8	2.059
C8···C11	2.584 (3)	H8···C10	2.013
C8···C12	3.020 (4)	H8···C11	2.035
C8···C13	2.566 (4)	H8···C12	2.758
C8···C15	2.672 (3)	H8···C13	3.303
C8···C18	3.155 (3)	H8···C14	2.735
C8···C19	2.550 (3)	H9···O1^iv	3.05
C8···H4	3.34	H9···N1^vii	3.102
C8···H5	2.933	H9···C1	2.899
C8···H6	2.056	H9···C2^iv	3.19
C8···H8	2.059	H9···C3^iv	3.08
C8···H9	3.384	H9···C8	3.384
C8···H10	2.814	H9···C9	2.046
C8···H11	3.317	H9···C10	2.772
C8···H13	2.005	H9···C12	2.04
C8···H14	2.987	H9···C13	3.3
C8···H15	2.86	H10···C1	2.805
C8···H18	2.935	H10···C8	2.814
C8···H19	3.329	H10···C9	2.047
C8···H22	2.843	H10···C10	2.704
C8···H23	2.593	H10···C12	2.046
C9···O1^iv	3.503 (2)	H10···C13	2.686
C9···C1	2.579 (3)	H10···C14	3.26
C9···C5	2.475 (4)	H10···C15^iii	3.364
C9···C6	2.748 (3)	H10···C18	2.728
C9···C7	2.580 (3)	H11···O2	3.01
C9···C8	1.562 (3)	H11···C1^iv	3.39
C9···C12	2.553 (4)	H11···C2^iv	3.329
C9···C13	2.953 (3)	H11···C3^iv	3.266
C9···C14	2.514 (3)	H11···C4^iv	3.288
C9···H1	2.759	H11···C5^iv	3.376
C9···H5	2.814	H11···C8	3.317
C9···H6	3.04	H11···C9	2.768
C9···H7	2.067	H11···C10^iv	3.412
C9···H9	2.046	H11···C11	2.058
C9···H10	2.047	H11···C13	2.041
C9···H11	2.768	H11···C14	2.691
C9···H12	3.36	H11···C17	2.729
C9···H13	2.648	H11···C18	3.349
C9···H18	3.293	H12···O2	2.948
C10···C2	2.425 (3)	H12···C9	3.36
C10···C3	2.804 (4)	H12···C11	2.052
C10···C4	2.422 (4)	H12···C13	2.044
C10···C6	2.473 (3)	H12···C14	3.329
C10···C7	2.961 (3)	H12···C16^viii	3.135
C10···C8	2.474 (3)	H12···C17	2.844
C10···C11	2.559 (4)	H12···C18	2.664
C10···H1	2.032	H13···O2	3.485
C10···H2	3.281	H13···C7	2.69
C10···H3	3.277	H13···C8	2.005
C10···H4	3.245	H13···C9	2.648
C10···H5	2.747	H13···C11	3.139
C10···H7	2.617	H13···C12	2.606
C10···H8	2.013	H13···C13	2.02
C10···H9	2.772	H13···C15	2.018
C10···H10	2.704	H13···C16	2.588
C10···H11^ii	3.412	H13···C17	2.517
C11···C1	2.951 (4)	H13···C18	3.355
C11···C8	2.584 (3)	H13···C19^iv	3.307
C11···C10	2.559 (4)	H13···C21^iv	3.509
C11···C13	2.487 (3)	H14···C7	3.031
C11···C14	2.918 (3)	H14···C8	2.987
C11···C18	3.055 (3)	H14···C13	3.257
C11···H1	2.602	H14···C14	2.086
C11···H7	2.811	H14···C16	2.089
C11···H8	2.035	H14···C17	3.207
C11···H11	2.058	H14···C19	3.201
C11···H12	2.052	H14···C21^iv	3.199
C11···H13	3.139	H15···O2^ii	3.551
C11···H15^iii	3.595	H15···C7	3.423
C11···H18	2.688	H15···C8	2.86
C11···H20	3.485	H15···C11^ix	3.595
C11···H21^iv	3.575	H15···C13	2.748
C12···O2	3.007 (3)	H15···C14	2.083
C12···C8	3.020 (4)	H15···C16	2.09
C12···C9	2.553 (4)	H15···C17	2.934
C12···C14	2.507 (3)	H15···C18	2.797
C12···C17	2.587 (4)	H15···C19	3.338
C12···C18	2.539 (3)	H16···O2	2.692
C12···H7	3.36	H16···C12^x	3.359
C12···H8	2.758	H16···C13	3.132
C12···H9	2.04	H16···C14	2.88
C12···H10	2.046	H16···C15	2.08
C12···H13	2.606	H16···C17	2.061
C12···H16^viii	3.359	H16···C19^iv	3.167
C12···H18	2.681	H16···C21^iv	3.116
C12···H19	3.341	H17···O2	2.759
C12···H20	2.781	H17···C1^ix	2.934
C13···O2	2.449 (3)	H17···C2^ix	3.197
C13···C8	2.566 (4)	H17···C13	3.06
C13···C9	2.953 (3)	H17···C14	3.161
C13···C11	2.487 (3)	H17···C15	2.079
C13···C14	1.542 (3)	H17···C17	2.058
C13···C15	2.428 (3)	H17···C18	3.324
C13···C16	2.470 (3)	H18···O2^ii	3.177
C13···C18	1.548 (3)	H18···C8	2.935
C13···H7	2.763	H18···C9	3.293
C13···H8	3.303	H18···C11	2.688
C13···H9	3.3	H18···C12	2.681
C13···H10	2.686	H18···C13	2.07
C13···H11	2.041	H18···C14	2.846
C13···H12	2.044	H18···C15	3.496
C13···H13	2.02	H18···C17	3.275
C13···H14	3.257	H18···C23^xi	3.475
C13···H15	2.748	H19···O2^ii	3.201
C13···H16	3.132	H19···O2	3.498
C13···H17	3.06	H19···C8	3.329
C13···H18	2.07	H19···C12	3.341
C13···H19	2.062	H19···C13	2.062
C13···H20	2.074	H19···C14	2.677
C14···O2	3.482 (3)	H19···C15	2.595
C14···C7	2.551 (4)	H19···C16	2.832
C14···C9	2.514 (3)	H19···C17	2.592
C14···C11	2.918 (3)	H19···C23^xi	3.267
C14···C12	2.507 (3)	H19···C24^xi	3.397
C14···C13	1.542 (3)	H20···O2	3.052
C14···C15	1.542 (3)	H20···C11	3.485
C14···C16	2.403 (4)	H20···C12	2.781
C14···C17	2.356 (4)	H20···C13	2.074
C14···C18	2.577 (3)	H20···C14	3.379
C14···C19	3.407 (3)	H20···C16	3.548
C14···H6	2.501	H20···C17	2.605
C14···H7	2.034	H20···C20^iii	3.242
C14···H8	2.735	H20···C21^iii	3.166
C14···H10	3.26	H20···C22^iii	3.38
C14···H11	2.691	H20···C23^xi	3.523
C14···H12	3.329	H21···N1^i	2.074
C14···H14	2.086	H21···C2	2.455
C14···H15	2.083	H21···C3	1.823
C14···H16	2.88	H21···C4	3.044
C14···H17	3.161	H21···C11^ii	3.575
C14···H18	2.846	H21···C24^i	3.135
C14···H19	2.677	H22···O2^ii	3.581
C14···H20	3.379	H22···C4	3.49
C14···H22^iv	3.308	H22···C5	2.978
C14···H23	3.115	H22···C6	2.598
C14···H26^iv	3.48	H22···C7	2.04
C15···C7	3.196 (4)	H22···C8	2.843
C15···C8	2.672 (3)	H22···C14^ii	3.308
C15···C13	2.428 (3)	H22···C16^ii	3.456
C15···C14	1.542 (3)	H22···C17^ii	3.308
C15···C16	1.548 (4)	H22···C20	2.044
C15···C17	2.455 (4)	H22···C21	2.652
C15···C18	2.996 (3)	H23···O2^ii	3.361
C15···C19	3.466 (4)	H23···C6	3.324
C15···H6	2.976	H23···C7	2.042
C15···H7	2.871	H23···C8	2.593
C15···H10^ix	3.364	H23···C14	3.115
C15···H13	2.018	H23···C15	2.842
C15···H16	2.08	H23···C16^ii	3.382
C15···H17	2.079	H23···C17^ii	3.422
C15···H18	3.496	H23···C20	2.034
C15···H19	2.595	H23···C21	2.776
C15···H23	2.842	H24···C6	2.806
C15···H26^iv	3.314	H24···C7	2.672
C15···H27^iv	3.437	H24···C19	2.037
C16···O2	2.434 (3)	H24···C21	2.034
C16···C13	2.470 (3)	H24···C22	2.734
C16···C14	2.403 (4)	H25···C7	2.809
C16···C15	1.548 (4)	H25···C18^ix	3.476
C16···C18	3.146 (4)	H25···C19	2.049
C16···H1^ix	3.355	H25···C21	2.039
C16···H12^x	3.135	H25···C22	2.697
C16···H13	2.588	H25···C23^iv	3.535
C16···H14	2.089	H26···C14^ii	3.48
C16···H15	2.09	H26···C15^ii	3.314
C16···H19	2.832	H26···C19	2.736
C16···H20	3.548	H26···C20	2.038
C16···H22^iv	3.456	H26···C22	2.029
C16···H23^iv	3.382	H26···C23	2.636
C16···H27^iv	3.229	H27···O2^ix	3.286
C17···C12	2.587 (4)	H27···C15^ii	3.437
C17···C14	2.356 (4)	H27···C16^ii	3.229
C17···C15	2.455 (4)	H27···C18^ix	3.521
C17···C18	2.439 (3)	H27···C19	2.692
C17···H11	2.729	H27···C20	2.032
C17···H12	2.844	H27···C22	2.039
C17···H13	2.517	H27···C23	2.708
C17···H14	3.207	H28···N1	3.543
C17···H15	2.934	H28···C20	2.7
C17···H16	2.061	H28···C21	2.047
C17···H17	2.058	H28···C23	2.059
C17···H18	3.275	H28···C24	2.711
C17···H19	2.592	H29···O2^ix	3.216
C17···H20	2.605	H29···N1	3.454
C17···H22^iv	3.308	H29···C18^ix	3.554
C17···H23^iv	3.422	H29···C20	2.755
C17···H31^iii	3.463	H29···C21	2.038
C18···O2	3.227 (3)	H29···C23	2.055
C18···C8	3.155 (3)	H29···C24	2.643
C18···C11	3.055 (3)	H30···N1	3.051
C18···C12	2.539 (3)	H30···C18^xii	3.572
C18···C13	1.548 (3)	H30···C20^ii	3.586
C18···C14	2.577 (3)	H30···C21	2.716
C18···C15	2.996 (3)	H30···C22	2.05
C18···C16	3.146 (4)	H30···C24	1.985
C18···C17	2.439 (3)	H31···O2^ix	2.392
C18···H7	2.844	H31···N1	3.055
C18···H10	2.728	H31···C17^ix	3.463
C18···H11	3.349	H31···C18^xii	2.945
C18···H12	2.664	H31···C21	2.643
C18···H13	3.355	H31···C22	2.054
C18···H15	2.797	H31···C24	1.985
C3—O1—H21	110.1	C18—C13—C12	111.7 (2)
C2—C1—C10	121.0 (2)	C15—C14—H13	105.6
C2—C1—H1	119.6	C15—C14—C8	121.1 (2)
C10—C1—H1	119.4	C15—C14—C13	103.9 (2)
C3—C2—H2	119.8	H13—C14—C8	105.8
C3—C2—C1	119.8 (2)	H13—C14—C13	105.8
H2—C2—C1	120.3	C8—C14—C13	113.5 (2)
C4—C3—O1	117.1 (2)	C16—C15—H14	111.2
C4—C3—C2	119.6 (2)	C16—C15—H15	111.3
O1—C3—C2	123.3 (2)	C16—C15—C14	102.1 (2)
C5—C4—H3	119.8	H14—C15—H15	109.5
C5—C4—C3	120.2 (2)	H14—C15—C14	111.5
H3—C4—C3	120.0	H15—C15—C14	111.1
C6—C5—C10	116.8 (2)	C17—C16—H16	110.4
C6—C5—C4	122.7 (2)	C17—C16—H17	110.2
C10—C5—C4	120.5 (2)	C17—C16—C15	105.9 (2)
C7—C6—H4	108.5	H16—C16—H17	109.5
C7—C6—H5	109.1	H16—C16—C15	110.5
C7—C6—C5	112.2 (2)	H17—C16—C15	110.4
H4—C6—H5	109.5	O2—C17—C13	126.7 (2)
H4—C6—C5	108.6	O2—C17—C16	125.2 (2)
H5—C6—C5	109.0	C13—C17—C16	108.0 (2)
C8—C7—C19	111.3 (2)	H18—C18—H19	109.5
C8—C7—H6	107.7	H18—C18—H20	109.5
C8—C7—C6	112.0 (2)	H18—C18—C13	109.6
C19—C7—H6	107.8	H19—C18—H20	109.5
C19—C7—C6	110.3 (2)	H19—C18—C13	108.9
H6—C7—C6	107.6	H20—C18—C13	109.9
C9—C8—C14	109.0 (2)	C20—C19—H22	108.7
C9—C8—H7	108.2	C20—C19—H23	107.8
C9—C8—C7	111.6 (2)	C20—C19—C7	113.8 (2)
C14—C8—H7	108.1	H22—C19—H23	109.5
C14—C8—C7	111.6 (2)	H22—C19—C7	108.4
H7—C8—C7	108.2	H23—C19—C7	108.6
C10—C9—C11	114.0 (2)	C21—C20—H24	108.4
C10—C9—H8	107.2	C21—C20—H25	108.9
C10—C9—C8	106.9 (2)	C21—C20—C19	112.9 (2)
C11—C9—H8	107.7	H24—C20—H25	109.5
C11—C9—C8	113.1 (2)	H24—C20—C19	108.1
H8—C9—C8	107.6	H25—C20—C19	109.1
C1—C10—C5	118.8 (2)	C22—C21—H26	108.2
C1—C10—C9	125.0 (2)	C22—C21—H27	109.0
C5—C10—C9	116.1 (2)	C22—C21—C20	113.2 (2)
C12—C11—H9	108.4	H26—C21—H27	109.5
C12—C11—H10	108.8	H26—C21—C20	108.7
C12—C11—C9	112.8 (2)	H27—C21—C20	108.3
H9—C11—H10	109.5	C23—C22—H28	109.4
H9—C11—C9	108.6	C23—C22—H29	109.0
H10—C11—C9	108.7	C23—C22—C21	110.4 (2)
C13—C12—H11	109.3	H28—C22—H29	109.5
C13—C12—H12	109.5	H28—C22—C21	109.7
C13—C12—C11	109.3 (2)	H29—C22—C21	109.0
H11—C12—H12	109.5	C24—C23—H30	109.0
H11—C12—C11	109.9	C24—C23—H31	109.0
H12—C12—C11	109.4	C24—C23—C22	111.9 (2)
C14—C13—C17	100.4 (2)	H30—C23—H31	109.5
C14—C13—C18	113.0 (2)	H30—C23—C22	108.6
C14—C13—C12	110.0 (2)	H31—C23—C22	108.9
C17—C13—C18	105.0 (2)	N1—C24—C23	177.6 (2)
C17—C13—C12	116.3 (2)
H21—O1—C3—C2	−12.4	H9—C11—C12—H12	63.3
H21—O1—C3—C4	168.7	H10—C11—C12—C13	64.2
C10—C1—C2—C3	0.6 (3)	H10—C11—C12—H11	−175.9
C10—C1—C2—H2	−179.3	H10—C11—C12—H12	−55.7
H1—C1—C2—C3	−179.3	C11—C12—C13—C14	58.6 (2)
H1—C1—C2—H2	0.8	C11—C12—C13—C17	171.7 (2)
C2—C1—C10—C5	1.2 (3)	C11—C12—C13—C18	−67.8 (3)
C2—C1—C10—C9	−175.6 (2)	H11—C12—C13—C14	−61.7
H1—C1—C10—C5	−178.9	H11—C12—C13—C17	51.5
H1—C1—C10—C9	4.3	H11—C12—C13—C18	172.0
C1—C2—C3—O1	179.9 (2)	H12—C12—C13—C14	178.4
C1—C2—C3—C4	−1.2 (3)	H12—C12—C13—C17	−68.4
H2—C2—C3—O1	−0.2	H12—C12—C13—C18	52.1
H2—C2—C3—C4	178.7	C12—C13—C14—C8	−59.8 (2)
O1—C3—C4—C5	179.0 (2)	C12—C13—C14—C15	166.8 (2)
O1—C3—C4—H3	−0.7	C12—C13—C14—H13	55.8
C2—C3—C4—C5	0.1 (3)	C17—C13—C14—C8	177.1 (2)
C2—C3—C4—H3	−179.6	C17—C13—C14—C15	43.7 (2)
C3—C4—C5—C6	−177.0 (2)	C17—C13—C14—H13	−67.3
C3—C4—C5—C10	1.7 (3)	C18—C13—C14—C8	65.8 (2)
H3—C4—C5—C6	2.8	C18—C13—C14—C15	−67.6 (2)
H3—C4—C5—C10	−178.6	C18—C13—C14—H13	−178.6
C4—C5—C6—C7	−129.7 (2)	C12—C13—C17—O2	29.8 (3)
C4—C5—C6—H4	−9.8	C12—C13—C17—C16	−148.6 (2)
C4—C5—C6—H5	109.3	C14—C13—C17—O2	148.3 (2)
C10—C5—C6—C7	51.6 (2)	C14—C13—C17—C16	−30.0 (2)
C10—C5—C6—H4	171.5	C18—C13—C17—O2	−94.3 (2)
C10—C5—C6—H5	−69.4	C18—C13—C17—C16	87.4 (2)
C4—C5—C10—C1	−2.3 (3)	C12—C13—C18—H18	53.3
C4—C5—C10—C9	174.7 (2)	C12—C13—C18—H19	173.0
C6—C5—C10—C1	176.4 (2)	C12—C13—C18—H20	−67.1
C6—C5—C10—C9	−6.5 (3)	C14—C13—C18—H18	−71.4
C5—C6—C7—C8	−35.8 (2)	C14—C13—C18—H19	48.3
C5—C6—C7—C19	88.8 (2)	C14—C13—C18—H20	168.3
C5—C6—C7—H6	−153.9	C17—C13—C18—H18	−179.8
H4—C6—C7—C8	−155.7	C17—C13—C18—H19	−60.1
H4—C6—C7—C19	−31.2	C17—C13—C18—H20	59.8
H4—C6—C7—H6	86.1	C8—C14—C15—C16	−169.8 (2)
H5—C6—C7—C8	85.1	C8—C14—C15—H14	71.4
H5—C6—C7—C19	−150.3	C8—C14—C15—H15	−51.0
H5—C6—C7—H6	−33.1	C13—C14—C15—C16	−40.8 (2)
C6—C7—C8—C9	−18.2 (2)	C13—C14—C15—H14	−159.7
C6—C7—C8—C14	−140.4 (2)	C13—C14—C15—H15	77.9
C6—C7—C8—H7	100.8	H13—C14—C15—C16	70.3
C19—C7—C8—C9	−142.2 (2)	H13—C14—C15—H14	−48.5
C19—C7—C8—C14	95.6 (2)	H13—C14—C15—H15	−170.9
C19—C7—C8—H7	−23.2	C14—C15—C16—C17	21.5 (2)
H6—C7—C8—C9	99.9	C14—C15—C16—H16	−98.1
H6—C7—C8—C14	−22.3	C14—C15—C16—H17	140.7
H6—C7—C8—H7	−141.1	H14—C15—C16—C17	140.5
C6—C7—C19—C20	73.3 (2)	H14—C15—C16—H16	20.9
C6—C7—C19—H22	−47.8	H14—C15—C16—H17	−100.3
C6—C7—C19—H23	−166.6	H15—C15—C16—C17	−97.2
C8—C7—C19—C20	−161.8 (2)	H15—C15—C16—H16	143.3
C8—C7—C19—H22	77.2	H15—C15—C16—H17	22.1
C8—C7—C19—H23	−41.7	C15—C16—C17—O2	−172.9 (2)
H6—C7—C19—C20	−43.9	C15—C16—C17—C13	5.5 (2)
H6—C7—C19—H22	−165.0	H16—C16—C17—O2	−53.3
H6—C7—C19—H23	76.2	H16—C16—C17—C13	125.1
C7—C8—C9—C10	60.3 (2)	H17—C16—C17—O2	67.7
C7—C8—C9—C11	−173.3 (2)	H17—C16—C17—C13	−113.9
C7—C8—C9—H8	−54.5	C7—C19—C20—C21	−170.5 (2)
C14—C8—C9—C10	−175.9 (2)	C7—C19—C20—H24	−50.6
C14—C8—C9—C11	−49.6 (2)	C7—C19—C20—H25	68.4
C14—C8—C9—H8	69.2	H22—C19—C20—C21	−49.6
H7—C8—C9—C10	−58.6	H22—C19—C20—H24	70.3
H7—C8—C9—C11	67.8	H22—C19—C20—H25	−170.7
H7—C8—C9—H8	−173.4	H23—C19—C20—C21	69.0
C7—C8—C14—C13	177.2 (2)	H23—C19—C20—H24	−171.1
C7—C8—C14—C15	−58.2 (2)	H23—C19—C20—H25	−52.1
C7—C8—C14—H13	61.6	C19—C20—C21—C22	−177.6 (2)
C9—C8—C14—C13	53.5 (2)	C19—C20—C21—H26	62.1
C9—C8—C14—C15	178.1 (2)	C19—C20—C21—H27	−56.7
C9—C8—C14—H13	−62.1	H24—C20—C21—C22	62.7
H7—C8—C14—C13	−63.9	H24—C20—C21—H26	−57.6
H7—C8—C14—C15	60.7	H24—C20—C21—H27	−176.4
H7—C8—C14—H13	−179.5	H25—C20—C21—C22	−56.3
C8—C9—C10—C1	128.3 (2)	H25—C20—C21—H26	−176.6
C8—C9—C10—C5	−48.5 (2)	H25—C20—C21—H27	64.6
C11—C9—C10—C1	2.5 (3)	C20—C21—C22—C23	−175.8 (2)
C11—C9—C10—C5	−174.3 (2)	C20—C21—C22—H28	−55.2
H8—C9—C10—C1	−116.5	C20—C21—C22—H29	64.6
H8—C9—C10—C5	66.6	H26—C21—C22—C23	−55.2
C8—C9—C11—C12	52.8 (2)	H26—C21—C22—H28	65.4
C8—C9—C11—H9	173.0	H26—C21—C22—H29	−174.8
C8—C9—C11—H10	−68.0	H27—C21—C22—C23	63.7
C10—C9—C11—C12	175.3 (2)	H27—C21—C22—H28	−175.7
C10—C9—C11—H9	−64.5	H27—C21—C22—H29	−55.9
C10—C9—C11—H10	54.5	C21—C22—C23—C24	−174.8 (2)
H8—C9—C11—C12	−66.0	C21—C22—C23—H30	64.9
H8—C9—C11—H9	54.2	C21—C22—C23—H31	−54.2
H8—C9—C11—H10	173.3	H28—C22—C23—C24	64.4
C9—C11—C12—C13	−56.5 (2)	H28—C22—C23—H30	−55.9
C9—C11—C12—H11	63.4	H28—C22—C23—H31	−175.0
C9—C11—C12—H12	−176.4	H29—C22—C23—C24	−55.2
H9—C11—C12—C13	−176.8	H29—C22—C23—H30	−175.5
H9—C11—C12—H11	−56.9	H29—C22—C23—H31	65.4

Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z; (iv) x+1, y, z; (v) x, y+1, z; (vi) x−1, y+1, z; (vii) x+1, y−1, z; (viii) −x+2, y−1/2, −z; (ix) −x+1, y+1/2, −z; (x) −x+2, y+1/2, −z; (xi) −x, y−1/2, −z; (xii) −x, y+1/2, −z.