1H-Indazole and 2H-indazole derivatives of androsta-5,16-dien-3β-ol

The title compounds, 17-(1H-indazol-1-yl)androsta-5,16-dien-3β-ol, (I), and 17-(2H-indazol-2-yl)androsta-5,16-dien-3β-ol, (II), both C₂₆H₃₂N₂O, have an indazole substituent at the C17 position. The six-membered B ring of each compound assumes a half-chair conformation. A twist of the steroid skeleton is observed and reproduced in quantum-mechanical ab initio calculations of the isolated mol­ecule using a mol­ecular orbital Hartree–Fock method. In the 1H-indazole derivative, (I), the mol­ecules are joined in a head-to-head fashion via O—H...O hydrogen bonds, forming chains along the a axis. In the 2H-indazole derivative, (II), the mol­ecules are joined in a head-to-tail fashion with one of the N atoms of the indazole ring system acting as the acceptor. The hydrogen-bond pattern consists of zigzag chains running along the b axis. Substituted steroids have proven to be effective in inhibiting androgen biosynthesis through coordination of the Fe atoms of some enzymes, and this study shows that indazole-substituted steroids adopt twisted conformations that restrict their intermolecular interactions.

S1. Comment

Androgen biosynthesis is mediated by the steroidal compound 17α-hydroxylase-C_17,20-lyase (CYP17), which catalyzes the conversion of C₂₁ precursors (pregnenolone and progesterone) to the related C₁₉ steroids (dehydroepiandrosterone and androstenedione) in the testis and the adrenals (Nakajin, Hall & Onoda, 1981; Nakajin, Shively et al., 1981; Nakajin & Hall, 1981; Zuber et al., 1986; Hall, 1991). Effective inhibitors of these enzymes could be useful in the treatment of androgen-dependent diseases, such as prostate cancer. A number of steroidal and nonsteroidal compounds which inhibit CYP17 have been reported (Barrie & Jarman, 1996; Jarman et al., 1998; Njar & Brodie, 1999; Hartmann et al., 2002; Leroux, 2005; Hakki & Bernhardt, 2006; Moreira et al., 2008). Amongst them, an interesting class of steroidal inhibitors has been reported in which the azole group is attached to position C17 of the steroid nucleus through an N atom (Njar et al., 1996, 1998; Handratta et al., 2005). Inhibitors of this class have shown potent inhibition of CYP17 as well as other important biological activities (Njar et al., 1998; Handratta et al., 2005). Attempts have been made to correlate the structure of the molecule with its lesser or greater ability to coordinate to the Fe atom of the haem group of the enzyme, thus inhibiting its function (Cavalli & Recanatini, 2002; Schappach & Holtje, 2001).

We report here the molecular structures of (I) and (II) determined by single-crystal X-ray analysis, and compare them with those of the free molecules as given by quantum-mechanical ab initio calculations and with 17-(3-pyridyl)androsta-5,16-dien-3β-ol, a related compound with potent inhibition properties of CYP17.

Molecular views of (I) and (II) are shown in Figs. 1 and 2. In both compounds, the A/B junction is quasi-trans and the remaining rings are trans fused. The hydroxy substituents at C3 are positioned in the beta face of the A rings, with angles to the Cremer & Pople (Cremer & Pople, 1975) normal of ring A of 70.30 (16) and 71.43 (11)°, respectively, for (I) and (II). Ring A exhibits the usual slightly flattened chair conformation with average torsion angles of 51.77 (15) and 51.89 (11)° for (I) and (II), respectively. Ring B, with two pairs of electrons shared between atoms C5 and C6, conforms to a half-chair shape, with average torsion angles of 35.6 (1) and 37.97 (10)° for (I) and (II), respectively. More specifically, for these rings, the puckering parameters (Cremer & Pople, 1975) are given in Table 3. They are roughly identical for both compounds, confirming the chair conformation for ring A and a conformation similar to a half-chair for ring B. Ring C exhibits the usual slightly flattened chair conformation with average torsion angles of 56.1 (1) and 54.80 (8)° for (I) and (II). Ring D, with a C16—C17 double bond, shows a conformation that can be described as envelope on C14 with P = 16.3 (3) and τ = 34.5 (2)° [P = 8.9 (2) and τ = 36.7 (2)° for (II)]. The substituents at C17 are in equatorial positions; the C17—N17A bond makes an angle of 87.8 (2)° to the normal of the Cremer & Pople plane in (I), and the C17—N17B bond makes an angle of 78.31 (15)° in (II). The pseudo-torsion angle C19—C10···C13—C18 that measures the twist of the steroid skeleton is 9.5 (5)° for (I) and 10.9 (5)° for (II). The distances between terminal atoms C3 and C17 are 8.684 (5) and 8.661 (5) Å for (I) and (II), respectively.

In order to check whether the large twist of the molecules is intrinsic to the free steroid molecule or due to intermolecular interactions, we performed a quantum-mechanical calculation of the equilibrium geometry of the free molecule. These calculations were performed using the computer program GAMESS (Schmidt et al., 1993). A molecular-orbital Roothan Hartree–Fock method was used with an extended 6–31 G(d,p) basis set. Tight conditions for convergence of both the self-consistent field cycles and the maximum density and energy gradients were imposed (10^-5 atomic units). The calculations reproduce the twist (calculated pseudo-torsion angle 10° and calculated C3···C17 distance of 8.7 Å for both compounds). Overall there is good agreement between the calculated and experimental parameters; the bond lengths do not differ by more than 0.02 Å and the bond angles differ by 3° at most. There is also good agreement in the orientation of the substituent indazole ring systems, showing the small freedom of rotation of the indazole group around the C17—N bond. For (I), the experimental torsion angle N17B—N17A—C17—C13 is -43.7 (4) and the calculated value is -43.7°. For (II), the N17A—N17B—C17—C13 torsion angle is 14.3 (3) and the calculated value is 14.4°.

There is a strong hydrogen-bond donor at the head of both compounds and possible acceptors in the tail but the hydrogen-bond networks are very different. In (I) there is a chain formation, with hydrogen bonds of the O—H···O type, joining the molecules head to head. The chains run along the a axis with a short periodicity of three elements (Table 1, Fig. 3). In (II), the molecules are joined head to tail, with atom N1 of the indazole ring system acting as an acceptor. Zigzag chains with a periodicity of 14 elements can be seen running along the b axis (Table 2, Fig. 4). In 17-(3-pyridyl)androsta-5,16-dien-3β-ol, the molecules are joined head to tail, the twist of the steroid skeleton is only 5.91°, the steroid length is 8.895 Å and the angle between the least-squares plane of ring D and of the C17 substituent ring is 30.58 (15)° (Burke et al., 1995).

Related literature

For related literature, see: Barrie & Jarman (1996); Burke et al. (1995); Cavalli & Recanatini (2002); Cremer & Pople (1975); Hakki & Bernhardt (2006); Hall (1991); Handratta et al. (2005); Hartmann et al. (2002); Jarman et al. (1998); Leroux (2005); Moreira et al. (2007, 2008); Nakajin & Hall (1981); Nakajin, Hall & Onoda (1981); Nakajin, Shively, Yuan & Hall (1981); Njar & Brodie (1999); Njar et al. (1996, 1998); Schappach & Holtje (2001); Schmidt et al. (1993); Zuber et al. (1986).

S2. Experimental

Both compounds were synthesized using the method reported previously by Moreira et al. (2007). Compound (I) was crystallized from acetone by slow evaporation. Compound (II) was crystallized from a mixture of acetonitrile and THF [Ratio of solvents?] by slow evaporation.

S3. Refinement

O-bound H atoms were located in a difference Fourier map and their positional parameters were refined, with U_iso(H) = 1.5U_eq(O). [Please check added text] All C-bound H atoms were refined as riding on their parent atoms, with C—H = 0.93–0.98 Å, and with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C). The absolute configuration was not determined from the X-ray data but was known from the synthesis route. Friedel pairs were merged before refinement.

Computing details

For both compounds, data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. A molecular view of compound (I), with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. A molecular view of compound (II), with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented as small spheres of arbitrary radii.
	Fig. 3. A partial packing view, showing the formation of chains in (I) through O—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonds have been omitted for clarity. [Symmetry code: (i) x - 1/2, 3/2 - y, 1 - z]
	Fig. 4. A partial packing view, showing the formation of zigzag chains in (II) through O—H···N hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonds have been omitted for clarity. [Symmetry code: (i) 1 - x, 1/2 + y, 1 - z]

(I) 17-(1H-indazol-1-yl)androsta-5,16-dien-3β-ol

Crystal data

C26H32N2O	F(000) = 840
Mr = 388.54	Dx = 1.218 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6240 reflections
a = 6.0445 (1) Å	θ = 3.0–28.7°
b = 12.1149 (2) Å	µ = 0.07 mm^−1
c = 28.9321 (4) Å	T = 293 K
V = 2118.66 (6) Å^3	Plate, colourless
Z = 4	0.22 × 0.15 × 0.03 mm

Data collection

Bruker APEX CCD area-detector diffractometer	2520 independent reflections
Radiation source: fine-focus sealed tube	1985 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
ϕ and ω scans	θmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −7→7
Tmin = 0.915, Tmax = 0.998	k = −15→15
48693 measured reflections	l = −36→36

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0926P)^2] where P = (Fo^2 + 2Fc^2)/3
2520 reflections	(Δ/σ)max < 0.001
267 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.24 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
C1	0.4403 (5)	0.8173 (3)	0.36614 (9)	0.0468 (8)
H1A	0.3467	0.8788	0.3573	0.056*
H1B	0.3552	0.7501	0.3621	0.056*
C2	0.5001 (5)	0.8291 (3)	0.41746 (9)	0.0512 (8)
H2A	0.5720	0.8997	0.4225	0.061*
H2B	0.3660	0.8275	0.4359	0.061*
C3	0.6510 (6)	0.7380 (3)	0.43266 (9)	0.0536 (8)
H3	0.5744	0.6672	0.4291	0.064*
O3	0.7171 (5)	0.7507 (3)	0.48018 (7)	0.0746 (8)
H3A	0.595 (9)	0.762 (5)	0.4899 (16)	0.112*
C4	0.8576 (6)	0.7370 (3)	0.40365 (9)	0.0497 (8)
H4A	0.9484	0.6744	0.4125	0.060*
H4B	0.9417	0.8036	0.4096	0.060*
C5	0.8071 (5)	0.7297 (2)	0.35240 (9)	0.0361 (6)
C6	0.9042 (5)	0.6553 (2)	0.32591 (9)	0.0423 (7)
H6	1.0004	0.6060	0.3402	0.051*
C7	0.8726 (5)	0.6433 (2)	0.27466 (8)	0.0412 (7)
H7A	0.7878	0.5769	0.2686	0.049*
H7B	1.0161	0.6349	0.2600	0.049*
C8	0.7537 (4)	0.7420 (2)	0.25322 (8)	0.0299 (5)
H8	0.8580	0.8035	0.2501	0.036*
C9	0.5607 (4)	0.7775 (2)	0.28491 (8)	0.0310 (6)
H9	0.4715	0.7110	0.2899	0.037*
C10	0.6419 (4)	0.8137 (2)	0.33351 (8)	0.0322 (6)
C11	0.4050 (5)	0.8621 (3)	0.26235 (8)	0.0422 (7)
H11A	0.4770	0.9337	0.2628	0.051*
H11B	0.2724	0.8678	0.2811	0.051*
C12	0.3358 (4)	0.8365 (3)	0.21234 (8)	0.0402 (7)
H12A	0.2380	0.7730	0.2119	0.048*
H12B	0.2563	0.8990	0.1995	0.048*
C13	0.5411 (4)	0.8126 (2)	0.18304 (8)	0.0309 (6)
C14	0.6586 (4)	0.7139 (2)	0.20589 (8)	0.0308 (6)
H14	0.5412	0.6601	0.2120	0.037*
C15	0.7994 (5)	0.6622 (2)	0.16715 (8)	0.0425 (7)
H15A	0.9427	0.6977	0.1645	0.051*
H15B	0.8199	0.5835	0.1718	0.051*
C16	0.6563 (5)	0.6856 (2)	0.12596 (9)	0.0459 (7)
H16	0.6666	0.6480	0.0980	0.055*
C17	0.5136 (5)	0.7660 (2)	0.13413 (8)	0.0378 (6)
N17A	0.3861 (4)	0.8210 (2)	0.10060 (8)	0.0450 (6)
N17B	0.1850 (4)	0.8643 (3)	0.11279 (9)	0.0543 (7)
C17A	0.1169 (6)	0.9223 (3)	0.07711 (10)	0.0582 (9)
H17A	−0.0172	0.9599	0.0761	0.070*
C17B	0.2723 (6)	0.9207 (3)	0.04034 (11)	0.0511 (8)
C17C	0.2849 (7)	0.9689 (3)	−0.00326 (12)	0.0642 (10)
H17C	0.1711	1.0134	−0.0143	0.077*
C17D	0.4690 (8)	0.9492 (3)	−0.02956 (12)	0.0709 (11)
H17D	0.4806	0.9810	−0.0587	0.085*
C17E	0.6395 (7)	0.8821 (3)	−0.01323 (11)	0.0648 (10)
H17E	0.7624	0.8703	−0.0319	0.078*
C17F	0.6318 (6)	0.8327 (3)	0.02974 (10)	0.0545 (8)
H17F	0.7453	0.7874	0.0403	0.065*
C17G	0.4450 (5)	0.8542 (3)	0.05654 (9)	0.0427 (7)
C18	0.6856 (5)	0.9158 (2)	0.17774 (10)	0.0432 (7)
H18A	0.8241	0.8959	0.1638	0.065*
H18B	0.7122	0.9477	0.2076	0.065*
H18C	0.6110	0.9686	0.1585	0.065*
C19	0.7532 (5)	0.9283 (2)	0.33242 (10)	0.0451 (7)
H19A	0.8232	0.9423	0.3616	0.068*
H19B	0.6434	0.9839	0.3267	0.068*
H19C	0.8622	0.9300	0.3083	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0380 (15)	0.072 (2)	0.0305 (14)	0.0023 (15)	0.0034 (13)	−0.0056 (14)
C2	0.0515 (18)	0.073 (2)	0.0292 (14)	0.0016 (18)	0.0085 (14)	−0.0046 (14)
C3	0.072 (2)	0.063 (2)	0.0263 (14)	−0.0065 (19)	−0.0028 (15)	0.0002 (14)
O3	0.099 (2)	0.0963 (19)	0.0280 (11)	0.005 (2)	−0.0096 (13)	0.0017 (13)
C4	0.0585 (19)	0.0552 (18)	0.0353 (15)	0.0070 (17)	−0.0097 (14)	−0.0001 (14)
C5	0.0369 (14)	0.0408 (15)	0.0307 (13)	−0.0009 (13)	−0.0045 (12)	0.0032 (12)
C6	0.0453 (15)	0.0425 (15)	0.0390 (15)	0.0091 (14)	−0.0085 (13)	0.0060 (12)
C7	0.0479 (16)	0.0400 (15)	0.0356 (14)	0.0109 (14)	−0.0025 (13)	0.0001 (12)
C8	0.0307 (12)	0.0303 (12)	0.0286 (12)	0.0023 (11)	0.0006 (10)	0.0005 (10)
C9	0.0276 (12)	0.0385 (14)	0.0268 (12)	−0.0009 (11)	−0.0001 (10)	0.0002 (11)
C10	0.0323 (13)	0.0384 (14)	0.0259 (12)	0.0017 (12)	0.0000 (11)	−0.0022 (11)
C11	0.0343 (14)	0.0612 (18)	0.0311 (13)	0.0163 (14)	−0.0002 (12)	−0.0053 (13)
C12	0.0339 (14)	0.0569 (17)	0.0298 (13)	0.0095 (14)	−0.0036 (12)	−0.0019 (13)
C13	0.0289 (12)	0.0370 (13)	0.0267 (12)	0.0015 (11)	−0.0025 (10)	−0.0013 (10)
C14	0.0313 (12)	0.0330 (13)	0.0280 (12)	−0.0007 (11)	0.0013 (10)	−0.0017 (10)
C15	0.0509 (16)	0.0437 (16)	0.0328 (14)	0.0127 (14)	0.0010 (13)	−0.0052 (12)
C16	0.0582 (18)	0.0521 (17)	0.0274 (14)	0.0055 (16)	0.0008 (14)	−0.0080 (12)
C17	0.0421 (15)	0.0450 (15)	0.0263 (13)	−0.0016 (14)	−0.0044 (12)	0.0000 (12)
N17A	0.0434 (13)	0.0607 (16)	0.0309 (12)	0.0068 (13)	−0.0031 (11)	0.0001 (11)
N17B	0.0419 (14)	0.0769 (18)	0.0441 (14)	0.0087 (14)	−0.0035 (12)	−0.0020 (14)
C17A	0.0534 (18)	0.072 (2)	0.0490 (18)	0.0118 (19)	−0.0126 (16)	−0.0005 (17)
C17B	0.062 (2)	0.0498 (17)	0.0418 (16)	−0.0034 (17)	−0.0131 (16)	0.0013 (14)
C17C	0.088 (3)	0.055 (2)	0.050 (2)	0.000 (2)	−0.016 (2)	0.0107 (16)
C17D	0.105 (3)	0.067 (2)	0.0410 (18)	−0.016 (2)	−0.010 (2)	0.0130 (17)
C17E	0.078 (2)	0.074 (2)	0.0422 (17)	−0.015 (2)	0.0074 (19)	0.0035 (17)
C17F	0.0587 (19)	0.063 (2)	0.0413 (17)	−0.0014 (17)	0.0014 (15)	0.0012 (15)
C17G	0.0503 (17)	0.0472 (17)	0.0306 (14)	−0.0070 (15)	−0.0076 (13)	−0.0019 (13)
C18	0.0475 (16)	0.0390 (15)	0.0430 (15)	−0.0024 (14)	−0.0042 (14)	0.0047 (12)
C19	0.0534 (18)	0.0412 (15)	0.0407 (15)	−0.0029 (15)	−0.0090 (14)	−0.0045 (12)

Geometric parameters (Å, º)

C1—C2	1.535 (4)	C12—H12B	0.9700
C1—C10	1.542 (4)	C13—C18	1.533 (4)
C1—H1A	0.9700	C13—C17	1.533 (3)
C1—H1B	0.9700	C13—C14	1.540 (3)
C2—C3	1.498 (5)	C14—C15	1.541 (3)
C2—H2A	0.9700	C14—H14	0.9800
C2—H2B	0.9700	C15—C16	1.499 (4)
C3—O3	1.440 (3)	C15—H15A	0.9700
C3—C4	1.505 (5)	C15—H15B	0.9700
C3—H3	0.9800	C16—C17	1.323 (4)
O3—H3A	0.80 (6)	C16—H16	0.9300
C4—C5	1.516 (4)	C17—N17A	1.407 (3)
C4—H4A	0.9700	N17A—N17B	1.370 (4)
C4—H4B	0.9700	N17A—C17G	1.383 (3)
C5—C6	1.322 (4)	N17B—C17A	1.315 (4)
C5—C10	1.526 (4)	C17A—C17B	1.419 (4)
C6—C7	1.502 (3)	C17A—H17A	0.9300
C6—H6	0.9300	C17B—C17C	1.392 (4)
C7—C8	1.527 (4)	C17B—C17G	1.400 (5)
C7—H7A	0.9700	C17C—C17D	1.369 (6)
C7—H7B	0.9700	C17C—H17C	0.9300
C8—C14	1.524 (3)	C17D—C17E	1.395 (6)
C8—C9	1.545 (3)	C17D—H17D	0.9300
C8—H8	0.9800	C17E—C17F	1.381 (4)
C9—C11	1.537 (4)	C17E—H17E	0.9300
C9—C10	1.553 (3)	C17F—C17G	1.394 (4)
C9—H9	0.9800	C17F—H17F	0.9300
C10—C19	1.543 (4)	C18—H18A	0.9600
C11—C12	1.538 (3)	C18—H18B	0.9600
C11—H11A	0.9700	C18—H18C	0.9600
C11—H11B	0.9700	C19—H19A	0.9600
C12—C13	1.530 (4)	C19—H19B	0.9600
C12—H12A	0.9700	C19—H19C	0.9600
C2—C1—C10	114.1 (2)	C13—C12—H12B	109.7
C2—C1—H1A	108.7	C11—C12—H12B	109.7
C10—C1—H1A	108.7	H12A—C12—H12B	108.2
C2—C1—H1B	108.7	C12—C13—C18	111.3 (2)
C10—C1—H1B	108.7	C12—C13—C17	119.6 (2)
H1A—C1—H1B	107.6	C18—C13—C17	105.7 (2)
C3—C2—C1	111.0 (3)	C12—C13—C14	106.4 (2)
C3—C2—H2A	109.4	C18—C13—C14	114.4 (2)
C1—C2—H2A	109.4	C17—C13—C14	99.2 (2)
C3—C2—H2B	109.4	C8—C14—C13	112.74 (19)
C1—C2—H2B	109.4	C8—C14—C15	122.4 (2)
H2A—C2—H2B	108.0	C13—C14—C15	104.98 (19)
O3—C3—C2	111.7 (3)	C8—C14—H14	105.1
O3—C3—C4	107.7 (3)	C13—C14—H14	105.1
C2—C3—C4	110.3 (3)	C15—C14—H14	105.1
O3—C3—H3	109.0	C16—C15—C14	100.5 (2)
C2—C3—H3	109.0	C16—C15—H15A	111.7
C4—C3—H3	109.0	C14—C15—H15A	111.7
C3—O3—H3A	96 (4)	C16—C15—H15B	111.7
C3—C4—C5	112.3 (3)	C14—C15—H15B	111.7
C3—C4—H4A	109.2	H15A—C15—H15B	109.4
C5—C4—H4A	109.2	C17—C16—C15	111.9 (2)
C3—C4—H4B	109.2	C17—C16—H16	124.0
C5—C4—H4B	109.2	C15—C16—H16	124.0
H4A—C4—H4B	107.9	C16—C17—N17A	125.7 (2)
C6—C5—C4	121.1 (3)	C16—C17—C13	111.5 (2)
C6—C5—C10	122.5 (2)	N17A—C17—C13	121.4 (2)
C4—C5—C10	116.3 (2)	N17B—N17A—C17G	110.8 (2)
C5—C6—C7	125.6 (3)	N17B—N17A—C17	119.3 (2)
C5—C6—H6	117.2	C17G—N17A—C17	129.2 (3)
C7—C6—H6	117.2	C17A—N17B—N17A	106.3 (3)
C6—C7—C8	112.7 (2)	N17B—C17A—C17B	112.0 (3)
C6—C7—H7A	109.1	N17B—C17A—H17A	124.0
C8—C7—H7A	109.1	C17B—C17A—H17A	124.0
C6—C7—H7B	109.1	C17C—C17B—C17G	120.3 (3)
C8—C7—H7B	109.1	C17C—C17B—C17A	135.2 (3)
H7A—C7—H7B	107.8	C17G—C17B—C17A	104.5 (3)
C14—C8—C7	111.6 (2)	C17D—C17C—C17B	118.3 (4)
C14—C8—C9	108.10 (19)	C17D—C17C—H17C	120.8
C7—C8—C9	109.4 (2)	C17B—C17C—H17C	120.8
C14—C8—H8	109.2	C17C—C17D—C17E	120.9 (3)
C7—C8—H8	109.2	C17C—C17D—H17D	119.5
C9—C8—H8	109.2	C17E—C17D—H17D	119.5
C11—C9—C8	113.33 (18)	C17F—C17E—C17D	122.2 (4)
C11—C9—C10	112.9 (2)	C17F—C17E—H17E	118.9
C8—C9—C10	112.2 (2)	C17D—C17E—H17E	118.9
C11—C9—H9	105.9	C17E—C17F—C17G	116.6 (3)
C8—C9—H9	105.9	C17E—C17F—H17F	121.7
C10—C9—H9	105.9	C17G—C17F—H17F	121.7
C5—C10—C1	108.5 (2)	N17A—C17G—C17F	131.8 (3)
C5—C10—C19	108.8 (2)	N17A—C17G—C17B	106.5 (3)
C1—C10—C19	109.4 (2)	C17F—C17G—C17B	121.7 (3)
C5—C10—C9	110.1 (2)	C13—C18—H18A	109.5
C1—C10—C9	108.2 (2)	C13—C18—H18B	109.5
C19—C10—C9	111.9 (2)	H18A—C18—H18B	109.5
C9—C11—C12	115.6 (2)	C13—C18—H18C	109.5
C9—C11—H11A	108.4	H18A—C18—H18C	109.5
C12—C11—H11A	108.4	H18B—C18—H18C	109.5
C9—C11—H11B	108.4	C10—C19—H19A	109.5
C12—C11—H11B	108.4	C10—C19—H19B	109.5
H11A—C11—H11B	107.5	H19A—C19—H19B	109.5
C13—C12—C11	109.8 (2)	C10—C19—H19C	109.5
C13—C12—H12A	109.7	H19A—C19—H19C	109.5
C11—C12—H12A	109.7	H19B—C19—H19C	109.5
C10—C1—C2—C3	−56.6 (4)	C12—C13—C14—C8	−67.1 (3)
C1—C2—C3—O3	177.3 (3)	C18—C13—C14—C8	56.2 (3)
C1—C2—C3—C4	57.5 (4)	C17—C13—C14—C8	168.2 (2)
O3—C3—C4—C5	−177.1 (3)	C12—C13—C14—C15	157.3 (2)
C2—C3—C4—C5	−54.9 (4)	C18—C13—C14—C15	−79.3 (3)
C3—C4—C5—C6	−129.3 (3)	C17—C13—C14—C15	32.6 (2)
C3—C4—C5—C10	51.5 (4)	C8—C14—C15—C16	−162.6 (2)
C4—C5—C6—C7	−177.8 (3)	C13—C14—C15—C16	−32.5 (3)
C10—C5—C6—C7	1.4 (5)	C14—C15—C16—C17	19.8 (3)
C5—C6—C7—C8	12.5 (4)	C15—C16—C17—N17A	167.5 (3)
C6—C7—C8—C14	−161.8 (2)	C15—C16—C17—C13	1.2 (3)
C6—C7—C8—C9	−42.2 (3)	C12—C13—C17—C16	−136.4 (3)
C14—C8—C9—C11	−47.8 (3)	C18—C13—C17—C16	97.2 (3)
C7—C8—C9—C11	−169.5 (2)	C14—C13—C17—C16	−21.5 (3)
C14—C8—C9—C10	−177.1 (2)	C12—C13—C17—N17A	56.6 (4)
C7—C8—C9—C10	61.2 (3)	C18—C13—C17—N17A	−69.8 (3)
C6—C5—C10—C1	133.9 (3)	C14—C13—C17—N17A	171.5 (2)
C4—C5—C10—C1	−46.8 (3)	C16—C17—N17A—N17B	151.3 (3)
C6—C5—C10—C19	−107.2 (3)	C13—C17—N17A—N17B	−43.7 (4)
C4—C5—C10—C19	72.0 (3)	C16—C17—N17A—C17G	−39.3 (5)
C6—C5—C10—C9	15.7 (4)	C13—C17—N17A—C17G	125.7 (3)
C4—C5—C10—C9	−165.0 (2)	C17G—N17A—N17B—C17A	0.8 (4)
C2—C1—C10—C5	49.0 (4)	C17—N17A—N17B—C17A	172.0 (3)
C2—C1—C10—C19	−69.4 (3)	N17A—N17B—C17A—C17B	−0.9 (4)
C2—C1—C10—C9	168.4 (2)	N17B—C17A—C17B—C17C	−178.0 (4)
C11—C9—C10—C5	−176.3 (2)	N17B—C17A—C17B—C17G	0.7 (4)
C8—C9—C10—C5	−46.7 (3)	C17G—C17B—C17C—C17D	0.2 (5)
C11—C9—C10—C1	65.4 (3)	C17A—C17B—C17C—C17D	178.8 (4)
C8—C9—C10—C1	−165.1 (2)	C17B—C17C—C17D—C17E	0.3 (6)
C11—C9—C10—C19	−55.2 (3)	C17C—C17D—C17E—C17F	0.0 (6)
C8—C9—C10—C19	74.4 (3)	C17D—C17E—C17F—C17G	−0.7 (5)
C8—C9—C11—C12	45.6 (3)	N17B—N17A—C17G—C17F	179.4 (3)
C10—C9—C11—C12	174.5 (2)	C17—N17A—C17G—C17F	9.2 (5)
C9—C11—C12—C13	−51.1 (3)	N17B—N17A—C17G—C17B	−0.4 (3)
C11—C12—C13—C18	−66.6 (3)	C17—N17A—C17G—C17B	−170.5 (3)
C11—C12—C13—C17	169.8 (2)	C17E—C17F—C17G—N17A	−178.5 (3)
C11—C12—C13—C14	58.7 (3)	C17E—C17F—C17G—C17B	1.2 (5)
C7—C8—C14—C13	−179.0 (2)	C17C—C17B—C17G—N17A	178.8 (3)
C9—C8—C14—C13	60.6 (3)	C17A—C17B—C17G—N17A	−0.2 (3)
C7—C8—C14—C15	−52.2 (3)	C17C—C17B—C17G—C17F	−1.0 (5)
C9—C8—C14—C15	−172.6 (2)	C17A—C17B—C17G—C17F	−179.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O3^i	0.80 (6)	2.45 (5)	3.233 (4)	167 (6)

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

(II) 17-(2H-indazol-2-yl)androsta-5,16-dien-3β-ol

Crystal data

C26H32N2O	F(000) = 420
Mr = 388.54	Dx = 1.218 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7226 reflections
a = 5.9234 (2) Å	θ = 2.8–29.1°
b = 13.0938 (4) Å	µ = 0.07 mm^−1
c = 13.6623 (4) Å	T = 293 K
β = 91.5347 (16)°	Plate, colourless
V = 1059.27 (6) Å^3	0.37 × 0.20 × 0.09 mm
Z = 2

Data collection

Bruker APEX CCD area-detector diffractometer	2855 independent reflections
Radiation source: fine-focus sealed tube	2446 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ϕ and ω scans	θmax = 28.8°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −7→8
Tmin = 0.884, Tmax = 0.993	k = −17→17
36122 measured reflections	l = −18→18

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0785P)^2 + 0.038P] where P = (Fo^2 + 2Fc^2)/3
2855 reflections	(Δ/σ)max < 0.001
267 parameters	Δρmax = 0.23 e Å^−3
1 restraint	Δρmin = −0.24 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
O3	0.6302 (4)	0.41643 (16)	0.16800 (12)	0.0666 (6)
H3	0.662 (7)	0.478 (4)	0.154 (3)	0.100*
N17A	0.2584 (3)	0.11661 (15)	0.91242 (12)	0.0416 (4)
N17B	0.3622 (3)	0.20350 (14)	0.94434 (11)	0.0371 (4)
C1	0.4073 (3)	0.2983 (2)	0.39492 (14)	0.0470 (6)
H1A	0.3267	0.2345	0.4030	0.056*
H1B	0.3082	0.3531	0.4147	0.056*
C2	0.4580 (4)	0.3118 (2)	0.28666 (16)	0.0511 (6)
H2A	0.5427	0.2534	0.2641	0.061*
H2B	0.3173	0.3151	0.2488	0.061*
C3	0.5922 (5)	0.40805 (19)	0.27049 (15)	0.0503 (6)
H3A	0.5030	0.4668	0.2912	0.060*
C4	0.8107 (4)	0.40472 (19)	0.33124 (16)	0.0493 (5)
H4A	0.9047	0.3497	0.3078	0.059*
H4B	0.8919	0.4683	0.3229	0.059*
C5	0.7687 (3)	0.38871 (16)	0.43875 (15)	0.0393 (4)
C6	0.8571 (4)	0.45046 (18)	0.50637 (17)	0.0503 (6)
H6	0.9425	0.5052	0.4848	0.060*
C7	0.8314 (4)	0.43969 (19)	0.61448 (18)	0.0517 (6)
H7A	0.7315	0.4929	0.6372	0.062*
H7B	0.9774	0.4491	0.6470	0.062*
C8	0.7364 (3)	0.33559 (17)	0.64287 (14)	0.0360 (4)
H8	0.8558	0.2841	0.6384	0.043*
C9	0.5403 (3)	0.30720 (15)	0.57108 (13)	0.0337 (4)
H9	0.4351	0.3649	0.5716	0.040*
C10	0.6193 (3)	0.29772 (15)	0.46398 (14)	0.0336 (4)
C11	0.4041 (3)	0.21290 (19)	0.60356 (14)	0.0412 (5)
H11A	0.2668	0.2089	0.5635	0.049*
H11B	0.4921	0.1521	0.5909	0.049*
C12	0.3400 (3)	0.21260 (18)	0.71183 (13)	0.0379 (4)
H12A	0.2284	0.2653	0.7230	0.046*
H12B	0.2740	0.1472	0.7282	0.046*
C13	0.5497 (3)	0.23190 (15)	0.77731 (13)	0.0328 (4)
C14	0.6482 (3)	0.33578 (16)	0.74632 (14)	0.0357 (4)
H14	0.5201	0.3831	0.7447	0.043*
C15	0.7970 (4)	0.36911 (19)	0.83481 (14)	0.0464 (5)
H15A	0.9476	0.3403	0.8322	0.056*
H15B	0.8076	0.4429	0.8395	0.056*
C16	0.6666 (4)	0.3247 (2)	0.91806 (15)	0.0456 (5)
H16	0.6852	0.3440	0.9833	0.055*
C17	0.5215 (3)	0.25411 (16)	0.88547 (14)	0.0365 (4)
C18	0.7215 (3)	0.14466 (17)	0.77007 (15)	0.0397 (4)
H18A	0.6641	0.0850	0.8018	0.060*
H18B	0.8615	0.1648	0.8015	0.060*
H18C	0.7464	0.1297	0.7024	0.060*
C19	0.7533 (4)	0.19869 (18)	0.44734 (16)	0.0450 (5)
H19A	0.6524	0.1413	0.4482	0.068*
H19B	0.8666	0.1911	0.4984	0.068*
H19C	0.8243	0.2019	0.3851	0.068*
C17A	0.2812 (4)	0.23922 (19)	1.02863 (17)	0.0488 (5)
H17A	0.3302	0.2969	1.0627	0.059*
C17B	0.1098 (4)	0.17287 (19)	1.05491 (17)	0.0479 (5)
C17C	−0.0504 (5)	0.1691 (2)	1.1304 (2)	0.0711 (8)
H17C	−0.0479	0.2173	1.1804	0.085*
C17D	−0.2065 (5)	0.0938 (2)	1.1278 (2)	0.0698 (8)
H17D	−0.3128	0.0907	1.1766	0.084*
C17E	−0.2120 (4)	0.0202 (2)	1.0533 (2)	0.0578 (6)
H17E	−0.3231	−0.0300	1.0539	0.069*
C17F	−0.0607 (4)	0.0195 (2)	0.98021 (17)	0.0501 (6)
H17F	−0.0645	−0.0307	0.9320	0.060*
C17G	0.1023 (3)	0.09810 (17)	0.98047 (14)	0.0390 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.1146 (16)	0.0562 (10)	0.0297 (8)	0.0036 (11)	0.0172 (9)	0.0081 (7)
N17A	0.0466 (9)	0.0503 (9)	0.0280 (8)	−0.0041 (8)	0.0019 (7)	−0.0006 (7)
N17B	0.0389 (8)	0.0455 (8)	0.0269 (8)	0.0008 (7)	0.0007 (6)	−0.0006 (7)
C1	0.0354 (10)	0.0795 (16)	0.0262 (10)	−0.0013 (11)	−0.0003 (8)	0.0074 (10)
C2	0.0467 (11)	0.0770 (17)	0.0296 (11)	0.0026 (11)	0.0010 (9)	0.0072 (10)
C3	0.0717 (15)	0.0531 (12)	0.0267 (10)	0.0173 (11)	0.0127 (10)	0.0070 (9)
C4	0.0591 (13)	0.0472 (12)	0.0422 (12)	−0.0067 (10)	0.0151 (10)	0.0047 (10)
C5	0.0392 (10)	0.0423 (10)	0.0369 (10)	0.0003 (9)	0.0085 (8)	0.0067 (8)
C6	0.0606 (13)	0.0456 (12)	0.0453 (12)	−0.0158 (11)	0.0085 (11)	0.0061 (10)
C7	0.0628 (14)	0.0500 (12)	0.0425 (12)	−0.0205 (11)	0.0031 (10)	−0.0008 (10)
C8	0.0336 (9)	0.0425 (9)	0.0320 (9)	−0.0066 (8)	0.0008 (7)	0.0015 (8)
C9	0.0301 (8)	0.0443 (10)	0.0266 (9)	0.0004 (7)	0.0007 (7)	0.0032 (7)
C10	0.0291 (8)	0.0424 (10)	0.0293 (9)	−0.0004 (8)	0.0015 (7)	0.0045 (7)
C11	0.0353 (9)	0.0614 (12)	0.0267 (9)	−0.0153 (10)	−0.0034 (7)	0.0050 (9)
C12	0.0294 (8)	0.0562 (12)	0.0281 (9)	−0.0066 (9)	−0.0009 (7)	0.0041 (9)
C13	0.0293 (8)	0.0451 (10)	0.0241 (8)	−0.0017 (7)	0.0000 (7)	0.0000 (7)
C14	0.0344 (9)	0.0426 (9)	0.0299 (9)	−0.0029 (8)	−0.0009 (7)	−0.0030 (8)
C15	0.0464 (11)	0.0578 (12)	0.0349 (11)	−0.0130 (10)	0.0001 (9)	−0.0104 (10)
C16	0.0485 (11)	0.0586 (13)	0.0296 (10)	−0.0044 (10)	−0.0013 (8)	−0.0073 (9)
C17	0.0358 (9)	0.0472 (11)	0.0263 (9)	0.0029 (8)	0.0008 (7)	−0.0008 (8)
C18	0.0364 (9)	0.0457 (11)	0.0369 (10)	0.0027 (8)	0.0012 (8)	0.0000 (8)
C19	0.0491 (11)	0.0435 (11)	0.0426 (12)	0.0026 (10)	0.0060 (9)	0.0016 (9)
C17A	0.0599 (13)	0.0499 (12)	0.0374 (11)	−0.0033 (10)	0.0149 (10)	−0.0074 (9)
C17B	0.0533 (13)	0.0502 (12)	0.0407 (12)	0.0032 (10)	0.0125 (10)	0.0006 (9)
C17C	0.0833 (19)	0.0662 (16)	0.0660 (17)	−0.0047 (15)	0.0422 (16)	−0.0143 (14)
C17D	0.0690 (17)	0.0664 (17)	0.0763 (19)	0.0021 (14)	0.0416 (15)	0.0076 (15)
C17E	0.0490 (13)	0.0637 (15)	0.0610 (16)	−0.0037 (11)	0.0056 (12)	0.0179 (13)
C17F	0.0527 (13)	0.0563 (13)	0.0411 (12)	−0.0051 (11)	−0.0016 (10)	0.0090 (10)
C17G	0.0391 (10)	0.0482 (11)	0.0297 (10)	0.0053 (8)	0.0008 (8)	0.0061 (8)

Geometric parameters (Å, º)

O3—C3	1.428 (3)	C11—H11A	0.9700
O3—H3	0.85 (5)	C11—H11B	0.9700
N17A—C17G	1.351 (3)	C12—C13	1.532 (2)
N17A—N17B	1.359 (3)	C12—H12A	0.9700
N17B—C17A	1.343 (3)	C12—H12B	0.9700
N17B—C17	1.420 (3)	C13—C17	1.520 (2)
C1—C2	1.528 (3)	C13—C18	1.535 (3)
C1—C10	1.550 (2)	C13—C14	1.544 (3)
C1—H1A	0.9700	C14—C15	1.540 (3)
C1—H1B	0.9700	C14—H14	0.9800
C2—C3	1.509 (4)	C15—C16	1.508 (3)
C2—H2A	0.9700	C15—H15A	0.9700
C2—H2B	0.9700	C15—H15B	0.9700
C3—C4	1.519 (3)	C16—C17	1.331 (3)
C3—H3A	0.9800	C16—H16	0.9300
C4—C5	1.511 (3)	C18—H18A	0.9600
C4—H4A	0.9700	C18—H18B	0.9600
C4—H4B	0.9700	C18—H18C	0.9600
C5—C6	1.325 (3)	C19—H19A	0.9600
C5—C10	1.529 (3)	C19—H19B	0.9600
C6—C7	1.496 (3)	C19—H19C	0.9600
C6—H6	0.9300	C17A—C17B	1.391 (3)
C7—C8	1.529 (3)	C17A—H17A	0.9300
C7—H7A	0.9700	C17B—C17G	1.412 (3)
C7—H7B	0.9700	C17B—C17C	1.421 (3)
C8—C14	1.520 (3)	C17C—C17D	1.352 (4)
C8—C9	1.545 (2)	C17C—H17C	0.9300
C8—H8	0.9800	C17D—C17E	1.401 (4)
C9—C11	1.546 (3)	C17D—H17D	0.9300
C9—C10	1.553 (3)	C17E—C17F	1.359 (4)
C9—H9	0.9800	C17E—H17E	0.9300
C10—C19	1.540 (3)	C17F—C17G	1.411 (3)
C11—C12	1.537 (3)	C17F—H17F	0.9300
C3—O3—H3	109 (3)	H11A—C11—H11B	107.5
C17G—N17A—N17B	103.96 (17)	C13—C12—C11	110.11 (15)
C17A—N17B—N17A	113.45 (17)	C13—C12—H12A	109.6
C17A—N17B—C17	125.50 (19)	C11—C12—H12A	109.6
N17A—N17B—C17	120.69 (16)	C13—C12—H12B	109.6
C2—C1—C10	114.38 (16)	C11—C12—H12B	109.6
C2—C1—H1A	108.7	H12A—C12—H12B	108.2
C10—C1—H1A	108.7	C17—C13—C12	119.38 (16)
C2—C1—H1B	108.7	C17—C13—C18	107.19 (15)
C10—C1—H1B	108.7	C12—C13—C18	111.61 (17)
H1A—C1—H1B	107.6	C17—C13—C14	98.64 (15)
C3—C2—C1	110.9 (2)	C12—C13—C14	106.97 (15)
C3—C2—H2A	109.5	C18—C13—C14	112.45 (15)
C1—C2—H2A	109.5	C8—C14—C15	121.80 (16)
C3—C2—H2B	109.5	C8—C14—C13	113.28 (16)
C1—C2—H2B	109.5	C15—C14—C13	104.30 (16)
H2A—C2—H2B	108.0	C8—C14—H14	105.4
O3—C3—C2	107.8 (2)	C15—C14—H14	105.4
O3—C3—C4	112.6 (2)	C13—C14—H14	105.4
C2—C3—C4	109.90 (18)	C16—C15—C14	100.90 (17)
O3—C3—H3A	108.8	C16—C15—H15A	111.6
C2—C3—H3A	108.8	C14—C15—H15A	111.6
C4—C3—H3A	108.8	C16—C15—H15B	111.6
C5—C4—C3	112.05 (18)	C14—C15—H15B	111.6
C5—C4—H4A	109.2	H15A—C15—H15B	109.4
C3—C4—H4A	109.2	C17—C16—C15	110.77 (18)
C5—C4—H4B	109.2	C17—C16—H16	124.6
C3—C4—H4B	109.2	C15—C16—H16	124.6
H4A—C4—H4B	107.9	C16—C17—N17B	124.59 (18)
C6—C5—C4	121.4 (2)	C16—C17—C13	111.80 (18)
C6—C5—C10	122.59 (19)	N17B—C17—C13	123.60 (17)
C4—C5—C10	116.02 (18)	C13—C18—H18A	109.5
C5—C6—C7	125.6 (2)	C13—C18—H18B	109.5
C5—C6—H6	117.2	H18A—C18—H18B	109.5
C7—C6—H6	117.2	C13—C18—H18C	109.5
C6—C7—C8	112.49 (19)	H18A—C18—H18C	109.5
C6—C7—H7A	109.1	H18B—C18—H18C	109.5
C8—C7—H7A	109.1	C10—C19—H19A	109.5
C6—C7—H7B	109.1	C10—C19—H19B	109.5
C8—C7—H7B	109.1	H19A—C19—H19B	109.5
H7A—C7—H7B	107.8	C10—C19—H19C	109.5
C14—C8—C7	111.86 (18)	H19A—C19—H19C	109.5
C14—C8—C9	108.63 (15)	H19B—C19—H19C	109.5
C7—C8—C9	109.20 (16)	N17B—C17A—C17B	106.5 (2)
C14—C8—H8	109.0	N17B—C17A—H17A	126.8
C7—C8—H8	109.0	C17B—C17A—H17A	126.8
C9—C8—H8	109.0	C17A—C17B—C17G	104.8 (2)
C8—C9—C11	113.51 (15)	C17A—C17B—C17C	135.7 (2)
C8—C9—C10	112.15 (15)	C17G—C17B—C17C	119.4 (2)
C11—C9—C10	112.28 (16)	C17D—C17C—C17B	118.4 (3)
C8—C9—H9	106.1	C17D—C17C—H17C	120.8
C11—C9—H9	106.1	C17B—C17C—H17C	120.8
C10—C9—H9	106.1	C17C—C17D—C17E	121.6 (2)
C5—C10—C19	108.58 (15)	C17C—C17D—H17D	119.2
C5—C10—C1	108.87 (17)	C17E—C17D—H17D	119.2
C19—C10—C1	109.05 (18)	C17F—C17E—C17D	122.3 (3)
C5—C10—C9	109.93 (16)	C17F—C17E—H17E	118.8
C19—C10—C9	112.07 (16)	C17D—C17E—H17E	118.8
C1—C10—C9	108.28 (15)	C17E—C17F—C17G	117.3 (2)
C12—C11—C9	115.00 (18)	C17E—C17F—H17F	121.4
C12—C11—H11A	108.5	C17G—C17F—H17F	121.4
C9—C11—H11A	108.5	N17A—C17G—C17F	127.6 (2)
C12—C11—H11B	108.5	N17A—C17G—C17B	111.3 (2)
C9—C11—H11B	108.5	C17F—C17G—C17B	121.1 (2)
C17G—N17A—N17B—C17A	0.7 (2)	C7—C8—C14—C13	179.67 (17)
C17G—N17A—N17B—C17	−172.76 (17)	C9—C8—C14—C13	59.1 (2)
C10—C1—C2—C3	−56.0 (3)	C17—C13—C14—C8	170.14 (15)
C1—C2—C3—O3	−179.14 (19)	C12—C13—C14—C8	−65.4 (2)
C1—C2—C3—C4	57.9 (2)	C18—C13—C14—C8	57.4 (2)
O3—C3—C4—C5	−176.15 (19)	C17—C13—C14—C15	35.58 (18)
C2—C3—C4—C5	−56.0 (3)	C12—C13—C14—C15	159.99 (17)
C3—C4—C5—C6	−127.6 (2)	C18—C13—C14—C15	−77.14 (19)
C3—C4—C5—C10	52.3 (3)	C8—C14—C15—C16	−162.65 (19)
C4—C5—C6—C7	−178.2 (2)	C13—C14—C15—C16	−33.0 (2)
C10—C5—C6—C7	1.8 (4)	C14—C15—C16—C17	17.1 (3)
C5—C6—C7—C8	13.2 (4)	C15—C16—C17—N17B	−175.08 (19)
C6—C7—C8—C14	−163.57 (19)	C15—C16—C17—C13	6.2 (3)
C6—C7—C8—C9	−43.3 (3)	C17A—N17B—C17—C16	23.2 (3)
C14—C8—C9—C11	−47.4 (2)	N17A—N17B—C17—C16	−164.2 (2)
C7—C8—C9—C11	−169.67 (19)	C17A—N17B—C17—C13	−158.3 (2)
C14—C8—C9—C10	−176.00 (16)	N17A—N17B—C17—C13	14.3 (3)
C7—C8—C9—C10	61.8 (2)	C12—C13—C17—C16	−141.6 (2)
C6—C5—C10—C19	−108.2 (2)	C18—C13—C17—C16	90.3 (2)
C4—C5—C10—C19	71.9 (2)	C14—C13—C17—C16	−26.5 (2)
C6—C5—C10—C1	133.2 (2)	C12—C13—C17—N17B	39.7 (3)
C4—C5—C10—C1	−46.7 (2)	C18—C13—C17—N17B	−88.4 (2)
C6—C5—C10—C9	14.7 (3)	C14—C13—C17—N17B	154.80 (18)
C4—C5—C10—C9	−165.22 (17)	N17A—N17B—C17A—C17B	−0.7 (3)
C2—C1—C10—C5	48.4 (3)	C17—N17B—C17A—C17B	172.36 (19)
C2—C1—C10—C19	−69.9 (3)	N17B—C17A—C17B—C17G	0.4 (3)
C2—C1—C10—C9	167.9 (2)	N17B—C17A—C17B—C17C	−175.5 (3)
C8—C9—C10—C5	−46.2 (2)	C17A—C17B—C17C—C17D	175.0 (3)
C11—C9—C10—C5	−175.41 (16)	C17G—C17B—C17C—C17D	−0.5 (4)
C8—C9—C10—C19	74.7 (2)	C17B—C17C—C17D—C17E	0.4 (5)
C11—C9—C10—C19	−54.6 (2)	C17C—C17D—C17E—C17F	0.6 (5)
C8—C9—C10—C1	−165.02 (18)	C17D—C17E—C17F—C17G	−1.4 (4)
C11—C9—C10—C1	65.8 (2)	N17B—N17A—C17G—C17F	176.43 (19)
C8—C9—C11—C12	46.0 (2)	N17B—N17A—C17G—C17B	−0.4 (2)
C10—C9—C11—C12	174.48 (16)	C17E—C17F—C17G—N17A	−175.3 (2)
C9—C11—C12—C13	−51.4 (2)	C17E—C17F—C17G—C17B	1.2 (3)
C11—C12—C13—C17	168.94 (19)	C17A—C17B—C17G—N17A	0.0 (3)
C11—C12—C13—C18	−65.1 (2)	C17C—C17B—C17G—N17A	176.7 (2)
C11—C12—C13—C14	58.3 (2)	C17A—C17B—C17G—C17F	−177.1 (2)
C7—C8—C14—C15	−54.6 (3)	C17C—C17B—C17G—C17F	−0.3 (4)
C9—C8—C14—C15	−175.26 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N17A^i	0.85 (5)	2.09 (5)	2.924 (3)	167 (4)

Symmetry code: (i) −x+1, y+1/2, −z+1.