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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108005842/dn3083sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108005842/dn3083Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108005842/dn3083IIsup3.hkl
Contains datablock II

CCDC references: 686440; 686441

Comment top

Androgen biosynthesis is mediated by the steroidal compound 17α-hydroxylase-C17,20-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 top

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).

Experimental top

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.

Refinement top

O-bound H atoms were located in a difference Fourier map and their positional parameters were refined, with Uiso(H) = 1.5Ueq(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 Uiso(H) = 1.2Ueq(C) or 1.5Ueq(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 top

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 top
[Figure 1] 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.
[Figure 2] 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.
[Figure 3] 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]
[Figure 4] 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 top
Crystal data top
C26H32N2OF(000) = 840
Mr = 388.54Dx = 1.218 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6240 reflections
a = 6.0445 (1) Åθ = 3.0–28.7°
b = 12.1149 (2) ŵ = 0.07 mm1
c = 28.9321 (4) ÅT = 293 K
V = 2118.66 (6) Å3Plate, colourless
Z = 40.22 × 0.15 × 0.03 mm
Data collection top
Bruker APEX CCD area-detector
diffractometer
2520 independent reflections
Radiation source: fine-focus sealed tube1985 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
ϕ and ω scansθmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
h = 77
Tmin = 0.915, Tmax = 0.998k = 1515
48693 measured reflectionsl = 3636
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0926P)2]
where P = (Fo2 + 2Fc2)/3
2520 reflections(Δ/σ)max < 0.001
267 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C26H32N2OV = 2118.66 (6) Å3
Mr = 388.54Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.0445 (1) ŵ = 0.07 mm1
b = 12.1149 (2) ÅT = 293 K
c = 28.9321 (4) Å0.22 × 0.15 × 0.03 mm
Data collection top
Bruker APEX CCD area-detector
diffractometer
2520 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
1985 reflections with I > 2σ(I)
Tmin = 0.915, Tmax = 0.998Rint = 0.057
48693 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.19 e Å3
2520 reflectionsΔρmin = 0.24 e Å3
267 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.4403 (5)0.8173 (3)0.36614 (9)0.0468 (8)
H1A0.34670.87880.35730.056*
H1B0.35520.75010.36210.056*
C20.5001 (5)0.8291 (3)0.41746 (9)0.0512 (8)
H2A0.57200.89970.42250.061*
H2B0.36600.82750.43590.061*
C30.6510 (6)0.7380 (3)0.43266 (9)0.0536 (8)
H30.57440.66720.42910.064*
O30.7171 (5)0.7507 (3)0.48018 (7)0.0746 (8)
H3A0.595 (9)0.762 (5)0.4899 (16)0.112*
C40.8576 (6)0.7370 (3)0.40365 (9)0.0497 (8)
H4A0.94840.67440.41250.060*
H4B0.94170.80360.40960.060*
C50.8071 (5)0.7297 (2)0.35240 (9)0.0361 (6)
C60.9042 (5)0.6553 (2)0.32591 (9)0.0423 (7)
H61.00040.60600.34020.051*
C70.8726 (5)0.6433 (2)0.27466 (8)0.0412 (7)
H7A0.78780.57690.26860.049*
H7B1.01610.63490.26000.049*
C80.7537 (4)0.7420 (2)0.25322 (8)0.0299 (5)
H80.85800.80350.25010.036*
C90.5607 (4)0.7775 (2)0.28491 (8)0.0310 (6)
H90.47150.71100.28990.037*
C100.6419 (4)0.8137 (2)0.33351 (8)0.0322 (6)
C110.4050 (5)0.8621 (3)0.26235 (8)0.0422 (7)
H11A0.47700.93370.26280.051*
H11B0.27240.86780.28110.051*
C120.3358 (4)0.8365 (3)0.21234 (8)0.0402 (7)
H12A0.23800.77300.21190.048*
H12B0.25630.89900.19950.048*
C130.5411 (4)0.8126 (2)0.18304 (8)0.0309 (6)
C140.6586 (4)0.7139 (2)0.20589 (8)0.0308 (6)
H140.54120.66010.21200.037*
C150.7994 (5)0.6622 (2)0.16715 (8)0.0425 (7)
H15A0.94270.69770.16450.051*
H15B0.81990.58350.17180.051*
C160.6563 (5)0.6856 (2)0.12596 (9)0.0459 (7)
H160.66660.64800.09800.055*
C170.5136 (5)0.7660 (2)0.13413 (8)0.0378 (6)
N17A0.3861 (4)0.8210 (2)0.10060 (8)0.0450 (6)
N17B0.1850 (4)0.8643 (3)0.11279 (9)0.0543 (7)
C17A0.1169 (6)0.9223 (3)0.07711 (10)0.0582 (9)
H17A0.01720.95990.07610.070*
C17B0.2723 (6)0.9207 (3)0.04034 (11)0.0511 (8)
C17C0.2849 (7)0.9689 (3)0.00326 (12)0.0642 (10)
H17C0.17111.01340.01430.077*
C17D0.4690 (8)0.9492 (3)0.02956 (12)0.0709 (11)
H17D0.48060.98100.05870.085*
C17E0.6395 (7)0.8821 (3)0.01323 (11)0.0648 (10)
H17E0.76240.87030.03190.078*
C17F0.6318 (6)0.8327 (3)0.02974 (10)0.0545 (8)
H17F0.74530.78740.04030.065*
C17G0.4450 (5)0.8542 (3)0.05654 (9)0.0427 (7)
C180.6856 (5)0.9158 (2)0.17774 (10)0.0432 (7)
H18A0.82410.89590.16380.065*
H18B0.71220.94770.20760.065*
H18C0.61100.96860.15850.065*
C190.7532 (5)0.9283 (2)0.33242 (10)0.0451 (7)
H19A0.82320.94230.36160.068*
H19B0.64340.98390.32670.068*
H19C0.86220.93000.30830.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0380 (15)0.072 (2)0.0305 (14)0.0023 (15)0.0034 (13)0.0056 (14)
C20.0515 (18)0.073 (2)0.0292 (14)0.0016 (18)0.0085 (14)0.0046 (14)
C30.072 (2)0.063 (2)0.0263 (14)0.0065 (19)0.0028 (15)0.0002 (14)
O30.099 (2)0.0963 (19)0.0280 (11)0.005 (2)0.0096 (13)0.0017 (13)
C40.0585 (19)0.0552 (18)0.0353 (15)0.0070 (17)0.0097 (14)0.0001 (14)
C50.0369 (14)0.0408 (15)0.0307 (13)0.0009 (13)0.0045 (12)0.0032 (12)
C60.0453 (15)0.0425 (15)0.0390 (15)0.0091 (14)0.0085 (13)0.0060 (12)
C70.0479 (16)0.0400 (15)0.0356 (14)0.0109 (14)0.0025 (13)0.0001 (12)
C80.0307 (12)0.0303 (12)0.0286 (12)0.0023 (11)0.0006 (10)0.0005 (10)
C90.0276 (12)0.0385 (14)0.0268 (12)0.0009 (11)0.0001 (10)0.0002 (11)
C100.0323 (13)0.0384 (14)0.0259 (12)0.0017 (12)0.0000 (11)0.0022 (11)
C110.0343 (14)0.0612 (18)0.0311 (13)0.0163 (14)0.0002 (12)0.0053 (13)
C120.0339 (14)0.0569 (17)0.0298 (13)0.0095 (14)0.0036 (12)0.0019 (13)
C130.0289 (12)0.0370 (13)0.0267 (12)0.0015 (11)0.0025 (10)0.0013 (10)
C140.0313 (12)0.0330 (13)0.0280 (12)0.0007 (11)0.0013 (10)0.0017 (10)
C150.0509 (16)0.0437 (16)0.0328 (14)0.0127 (14)0.0010 (13)0.0052 (12)
C160.0582 (18)0.0521 (17)0.0274 (14)0.0055 (16)0.0008 (14)0.0080 (12)
C170.0421 (15)0.0450 (15)0.0263 (13)0.0016 (14)0.0044 (12)0.0000 (12)
N17A0.0434 (13)0.0607 (16)0.0309 (12)0.0068 (13)0.0031 (11)0.0001 (11)
N17B0.0419 (14)0.0769 (18)0.0441 (14)0.0087 (14)0.0035 (12)0.0020 (14)
C17A0.0534 (18)0.072 (2)0.0490 (18)0.0118 (19)0.0126 (16)0.0005 (17)
C17B0.062 (2)0.0498 (17)0.0418 (16)0.0034 (17)0.0131 (16)0.0013 (14)
C17C0.088 (3)0.055 (2)0.050 (2)0.000 (2)0.016 (2)0.0107 (16)
C17D0.105 (3)0.067 (2)0.0410 (18)0.016 (2)0.010 (2)0.0130 (17)
C17E0.078 (2)0.074 (2)0.0422 (17)0.015 (2)0.0074 (19)0.0035 (17)
C17F0.0587 (19)0.063 (2)0.0413 (17)0.0014 (17)0.0014 (15)0.0012 (15)
C17G0.0503 (17)0.0472 (17)0.0306 (14)0.0070 (15)0.0076 (13)0.0019 (13)
C180.0475 (16)0.0390 (15)0.0430 (15)0.0024 (14)0.0042 (14)0.0047 (12)
C190.0534 (18)0.0412 (15)0.0407 (15)0.0029 (15)0.0090 (14)0.0045 (12)
Geometric parameters (Å, º) top
C1—C21.535 (4)C12—H12B0.9700
C1—C101.542 (4)C13—C181.533 (4)
C1—H1A0.9700C13—C171.533 (3)
C1—H1B0.9700C13—C141.540 (3)
C2—C31.498 (5)C14—C151.541 (3)
C2—H2A0.9700C14—H140.9800
C2—H2B0.9700C15—C161.499 (4)
C3—O31.440 (3)C15—H15A0.9700
C3—C41.505 (5)C15—H15B0.9700
C3—H30.9800C16—C171.323 (4)
O3—H3A0.80 (6)C16—H160.9300
C4—C51.516 (4)C17—N17A1.407 (3)
C4—H4A0.9700N17A—N17B1.370 (4)
C4—H4B0.9700N17A—C17G1.383 (3)
C5—C61.322 (4)N17B—C17A1.315 (4)
C5—C101.526 (4)C17A—C17B1.419 (4)
C6—C71.502 (3)C17A—H17A0.9300
C6—H60.9300C17B—C17C1.392 (4)
C7—C81.527 (4)C17B—C17G1.400 (5)
C7—H7A0.9700C17C—C17D1.369 (6)
C7—H7B0.9700C17C—H17C0.9300
C8—C141.524 (3)C17D—C17E1.395 (6)
C8—C91.545 (3)C17D—H17D0.9300
C8—H80.9800C17E—C17F1.381 (4)
C9—C111.537 (4)C17E—H17E0.9300
C9—C101.553 (3)C17F—C17G1.394 (4)
C9—H90.9800C17F—H17F0.9300
C10—C191.543 (4)C18—H18A0.9600
C11—C121.538 (3)C18—H18B0.9600
C11—H11A0.9700C18—H18C0.9600
C11—H11B0.9700C19—H19A0.9600
C12—C131.530 (4)C19—H19B0.9600
C12—H12A0.9700C19—H19C0.9600
C2—C1—C10114.1 (2)C13—C12—H12B109.7
C2—C1—H1A108.7C11—C12—H12B109.7
C10—C1—H1A108.7H12A—C12—H12B108.2
C2—C1—H1B108.7C12—C13—C18111.3 (2)
C10—C1—H1B108.7C12—C13—C17119.6 (2)
H1A—C1—H1B107.6C18—C13—C17105.7 (2)
C3—C2—C1111.0 (3)C12—C13—C14106.4 (2)
C3—C2—H2A109.4C18—C13—C14114.4 (2)
C1—C2—H2A109.4C17—C13—C1499.2 (2)
C3—C2—H2B109.4C8—C14—C13112.74 (19)
C1—C2—H2B109.4C8—C14—C15122.4 (2)
H2A—C2—H2B108.0C13—C14—C15104.98 (19)
O3—C3—C2111.7 (3)C8—C14—H14105.1
O3—C3—C4107.7 (3)C13—C14—H14105.1
C2—C3—C4110.3 (3)C15—C14—H14105.1
O3—C3—H3109.0C16—C15—C14100.5 (2)
C2—C3—H3109.0C16—C15—H15A111.7
C4—C3—H3109.0C14—C15—H15A111.7
C3—O3—H3A96 (4)C16—C15—H15B111.7
C3—C4—C5112.3 (3)C14—C15—H15B111.7
C3—C4—H4A109.2H15A—C15—H15B109.4
C5—C4—H4A109.2C17—C16—C15111.9 (2)
C3—C4—H4B109.2C17—C16—H16124.0
C5—C4—H4B109.2C15—C16—H16124.0
H4A—C4—H4B107.9C16—C17—N17A125.7 (2)
C6—C5—C4121.1 (3)C16—C17—C13111.5 (2)
C6—C5—C10122.5 (2)N17A—C17—C13121.4 (2)
C4—C5—C10116.3 (2)N17B—N17A—C17G110.8 (2)
C5—C6—C7125.6 (3)N17B—N17A—C17119.3 (2)
C5—C6—H6117.2C17G—N17A—C17129.2 (3)
C7—C6—H6117.2C17A—N17B—N17A106.3 (3)
C6—C7—C8112.7 (2)N17B—C17A—C17B112.0 (3)
C6—C7—H7A109.1N17B—C17A—H17A124.0
C8—C7—H7A109.1C17B—C17A—H17A124.0
C6—C7—H7B109.1C17C—C17B—C17G120.3 (3)
C8—C7—H7B109.1C17C—C17B—C17A135.2 (3)
H7A—C7—H7B107.8C17G—C17B—C17A104.5 (3)
C14—C8—C7111.6 (2)C17D—C17C—C17B118.3 (4)
C14—C8—C9108.10 (19)C17D—C17C—H17C120.8
C7—C8—C9109.4 (2)C17B—C17C—H17C120.8
C14—C8—H8109.2C17C—C17D—C17E120.9 (3)
C7—C8—H8109.2C17C—C17D—H17D119.5
C9—C8—H8109.2C17E—C17D—H17D119.5
C11—C9—C8113.33 (18)C17F—C17E—C17D122.2 (4)
C11—C9—C10112.9 (2)C17F—C17E—H17E118.9
C8—C9—C10112.2 (2)C17D—C17E—H17E118.9
C11—C9—H9105.9C17E—C17F—C17G116.6 (3)
C8—C9—H9105.9C17E—C17F—H17F121.7
C10—C9—H9105.9C17G—C17F—H17F121.7
C5—C10—C1108.5 (2)N17A—C17G—C17F131.8 (3)
C5—C10—C19108.8 (2)N17A—C17G—C17B106.5 (3)
C1—C10—C19109.4 (2)C17F—C17G—C17B121.7 (3)
C5—C10—C9110.1 (2)C13—C18—H18A109.5
C1—C10—C9108.2 (2)C13—C18—H18B109.5
C19—C10—C9111.9 (2)H18A—C18—H18B109.5
C9—C11—C12115.6 (2)C13—C18—H18C109.5
C9—C11—H11A108.4H18A—C18—H18C109.5
C12—C11—H11A108.4H18B—C18—H18C109.5
C9—C11—H11B108.4C10—C19—H19A109.5
C12—C11—H11B108.4C10—C19—H19B109.5
H11A—C11—H11B107.5H19A—C19—H19B109.5
C13—C12—C11109.8 (2)C10—C19—H19C109.5
C13—C12—H12A109.7H19A—C19—H19C109.5
C11—C12—H12A109.7H19B—C19—H19C109.5
C10—C1—C2—C356.6 (4)C12—C13—C14—C867.1 (3)
C1—C2—C3—O3177.3 (3)C18—C13—C14—C856.2 (3)
C1—C2—C3—C457.5 (4)C17—C13—C14—C8168.2 (2)
O3—C3—C4—C5177.1 (3)C12—C13—C14—C15157.3 (2)
C2—C3—C4—C554.9 (4)C18—C13—C14—C1579.3 (3)
C3—C4—C5—C6129.3 (3)C17—C13—C14—C1532.6 (2)
C3—C4—C5—C1051.5 (4)C8—C14—C15—C16162.6 (2)
C4—C5—C6—C7177.8 (3)C13—C14—C15—C1632.5 (3)
C10—C5—C6—C71.4 (5)C14—C15—C16—C1719.8 (3)
C5—C6—C7—C812.5 (4)C15—C16—C17—N17A167.5 (3)
C6—C7—C8—C14161.8 (2)C15—C16—C17—C131.2 (3)
C6—C7—C8—C942.2 (3)C12—C13—C17—C16136.4 (3)
C14—C8—C9—C1147.8 (3)C18—C13—C17—C1697.2 (3)
C7—C8—C9—C11169.5 (2)C14—C13—C17—C1621.5 (3)
C14—C8—C9—C10177.1 (2)C12—C13—C17—N17A56.6 (4)
C7—C8—C9—C1061.2 (3)C18—C13—C17—N17A69.8 (3)
C6—C5—C10—C1133.9 (3)C14—C13—C17—N17A171.5 (2)
C4—C5—C10—C146.8 (3)C16—C17—N17A—N17B151.3 (3)
C6—C5—C10—C19107.2 (3)C13—C17—N17A—N17B43.7 (4)
C4—C5—C10—C1972.0 (3)C16—C17—N17A—C17G39.3 (5)
C6—C5—C10—C915.7 (4)C13—C17—N17A—C17G125.7 (3)
C4—C5—C10—C9165.0 (2)C17G—N17A—N17B—C17A0.8 (4)
C2—C1—C10—C549.0 (4)C17—N17A—N17B—C17A172.0 (3)
C2—C1—C10—C1969.4 (3)N17A—N17B—C17A—C17B0.9 (4)
C2—C1—C10—C9168.4 (2)N17B—C17A—C17B—C17C178.0 (4)
C11—C9—C10—C5176.3 (2)N17B—C17A—C17B—C17G0.7 (4)
C8—C9—C10—C546.7 (3)C17G—C17B—C17C—C17D0.2 (5)
C11—C9—C10—C165.4 (3)C17A—C17B—C17C—C17D178.8 (4)
C8—C9—C10—C1165.1 (2)C17B—C17C—C17D—C17E0.3 (6)
C11—C9—C10—C1955.2 (3)C17C—C17D—C17E—C17F0.0 (6)
C8—C9—C10—C1974.4 (3)C17D—C17E—C17F—C17G0.7 (5)
C8—C9—C11—C1245.6 (3)N17B—N17A—C17G—C17F179.4 (3)
C10—C9—C11—C12174.5 (2)C17—N17A—C17G—C17F9.2 (5)
C9—C11—C12—C1351.1 (3)N17B—N17A—C17G—C17B0.4 (3)
C11—C12—C13—C1866.6 (3)C17—N17A—C17G—C17B170.5 (3)
C11—C12—C13—C17169.8 (2)C17E—C17F—C17G—N17A178.5 (3)
C11—C12—C13—C1458.7 (3)C17E—C17F—C17G—C17B1.2 (5)
C7—C8—C14—C13179.0 (2)C17C—C17B—C17G—N17A178.8 (3)
C9—C8—C14—C1360.6 (3)C17A—C17B—C17G—N17A0.2 (3)
C7—C8—C14—C1552.2 (3)C17C—C17B—C17G—C17F1.0 (5)
C9—C8—C14—C15172.6 (2)C17A—C17B—C17G—C17F179.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O3i0.80 (6)2.45 (5)3.233 (4)167 (6)
Symmetry code: (i) x1/2, y+3/2, z+1.
(II) 17-(2H-indazol-2-yl)androsta-5,16-dien-3β-ol top
Crystal data top
C26H32N2OF(000) = 420
Mr = 388.54Dx = 1.218 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 7226 reflections
a = 5.9234 (2) Åθ = 2.8–29.1°
b = 13.0938 (4) ŵ = 0.07 mm1
c = 13.6623 (4) ÅT = 293 K
β = 91.5347 (16)°Plate, colourless
V = 1059.27 (6) Å30.37 × 0.20 × 0.09 mm
Z = 2
Data collection top
Bruker APEX CCD area-detector
diffractometer
2855 independent reflections
Radiation source: fine-focus sealed tube2446 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ϕ and ω scansθmax = 28.8°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
h = 78
Tmin = 0.884, Tmax = 0.993k = 1717
36122 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0785P)2 + 0.038P]
where P = (Fo2 + 2Fc2)/3
2855 reflections(Δ/σ)max < 0.001
267 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = 0.24 e Å3
Crystal data top
C26H32N2OV = 1059.27 (6) Å3
Mr = 388.54Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.9234 (2) ŵ = 0.07 mm1
b = 13.0938 (4) ÅT = 293 K
c = 13.6623 (4) Å0.37 × 0.20 × 0.09 mm
β = 91.5347 (16)°
Data collection top
Bruker APEX CCD area-detector
diffractometer
2855 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
2446 reflections with I > 2σ(I)
Tmin = 0.884, Tmax = 0.993Rint = 0.032
36122 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0381 restraint
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.23 e Å3
2855 reflectionsΔρmin = 0.24 e Å3
267 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
O30.6302 (4)0.41643 (16)0.16800 (12)0.0666 (6)
H30.662 (7)0.478 (4)0.154 (3)0.100*
N17A0.2584 (3)0.11661 (15)0.91242 (12)0.0416 (4)
N17B0.3622 (3)0.20350 (14)0.94434 (11)0.0371 (4)
C10.4073 (3)0.2983 (2)0.39492 (14)0.0470 (6)
H1A0.32670.23450.40300.056*
H1B0.30820.35310.41470.056*
C20.4580 (4)0.3118 (2)0.28666 (16)0.0511 (6)
H2A0.54270.25340.26410.061*
H2B0.31730.31510.24880.061*
C30.5922 (5)0.40805 (19)0.27049 (15)0.0503 (6)
H3A0.50300.46680.29120.060*
C40.8107 (4)0.40472 (19)0.33124 (16)0.0493 (5)
H4A0.90470.34970.30780.059*
H4B0.89190.46830.32290.059*
C50.7687 (3)0.38871 (16)0.43875 (15)0.0393 (4)
C60.8571 (4)0.45046 (18)0.50637 (17)0.0503 (6)
H60.94250.50520.48480.060*
C70.8314 (4)0.43969 (19)0.61448 (18)0.0517 (6)
H7A0.73150.49290.63720.062*
H7B0.97740.44910.64700.062*
C80.7364 (3)0.33559 (17)0.64287 (14)0.0360 (4)
H80.85580.28410.63840.043*
C90.5403 (3)0.30720 (15)0.57108 (13)0.0337 (4)
H90.43510.36490.57160.040*
C100.6193 (3)0.29772 (15)0.46398 (14)0.0336 (4)
C110.4041 (3)0.21290 (19)0.60356 (14)0.0412 (5)
H11A0.26680.20890.56350.049*
H11B0.49210.15210.59090.049*
C120.3400 (3)0.21260 (18)0.71183 (13)0.0379 (4)
H12A0.22840.26530.72300.046*
H12B0.27400.14720.72820.046*
C130.5497 (3)0.23190 (15)0.77731 (13)0.0328 (4)
C140.6482 (3)0.33578 (16)0.74632 (14)0.0357 (4)
H140.52010.38310.74470.043*
C150.7970 (4)0.36911 (19)0.83481 (14)0.0464 (5)
H15A0.94760.34030.83220.056*
H15B0.80760.44290.83950.056*
C160.6666 (4)0.3247 (2)0.91806 (15)0.0456 (5)
H160.68520.34400.98330.055*
C170.5215 (3)0.25411 (16)0.88547 (14)0.0365 (4)
C180.7215 (3)0.14466 (17)0.77007 (15)0.0397 (4)
H18A0.66410.08500.80180.060*
H18B0.86150.16480.80150.060*
H18C0.74640.12970.70240.060*
C190.7533 (4)0.19869 (18)0.44734 (16)0.0450 (5)
H19A0.65240.14130.44820.068*
H19B0.86660.19110.49840.068*
H19C0.82430.20190.38510.068*
C17A0.2812 (4)0.23922 (19)1.02863 (17)0.0488 (5)
H17A0.33020.29691.06270.059*
C17B0.1098 (4)0.17287 (19)1.05491 (17)0.0479 (5)
C17C0.0504 (5)0.1691 (2)1.1304 (2)0.0711 (8)
H17C0.04790.21731.18040.085*
C17D0.2065 (5)0.0938 (2)1.1278 (2)0.0698 (8)
H17D0.31280.09071.17660.084*
C17E0.2120 (4)0.0202 (2)1.0533 (2)0.0578 (6)
H17E0.32310.03001.05390.069*
C17F0.0607 (4)0.0195 (2)0.98021 (17)0.0501 (6)
H17F0.06450.03070.93200.060*
C17G0.1023 (3)0.09810 (17)0.98047 (14)0.0390 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.1146 (16)0.0562 (10)0.0297 (8)0.0036 (11)0.0172 (9)0.0081 (7)
N17A0.0466 (9)0.0503 (9)0.0280 (8)0.0041 (8)0.0019 (7)0.0006 (7)
N17B0.0389 (8)0.0455 (8)0.0269 (8)0.0008 (7)0.0007 (6)0.0006 (7)
C10.0354 (10)0.0795 (16)0.0262 (10)0.0013 (11)0.0003 (8)0.0074 (10)
C20.0467 (11)0.0770 (17)0.0296 (11)0.0026 (11)0.0010 (9)0.0072 (10)
C30.0717 (15)0.0531 (12)0.0267 (10)0.0173 (11)0.0127 (10)0.0070 (9)
C40.0591 (13)0.0472 (12)0.0422 (12)0.0067 (10)0.0151 (10)0.0047 (10)
C50.0392 (10)0.0423 (10)0.0369 (10)0.0003 (9)0.0085 (8)0.0067 (8)
C60.0606 (13)0.0456 (12)0.0453 (12)0.0158 (11)0.0085 (11)0.0061 (10)
C70.0628 (14)0.0500 (12)0.0425 (12)0.0205 (11)0.0031 (10)0.0008 (10)
C80.0336 (9)0.0425 (9)0.0320 (9)0.0066 (8)0.0008 (7)0.0015 (8)
C90.0301 (8)0.0443 (10)0.0266 (9)0.0004 (7)0.0007 (7)0.0032 (7)
C100.0291 (8)0.0424 (10)0.0293 (9)0.0004 (8)0.0015 (7)0.0045 (7)
C110.0353 (9)0.0614 (12)0.0267 (9)0.0153 (10)0.0034 (7)0.0050 (9)
C120.0294 (8)0.0562 (12)0.0281 (9)0.0066 (9)0.0009 (7)0.0041 (9)
C130.0293 (8)0.0451 (10)0.0241 (8)0.0017 (7)0.0000 (7)0.0000 (7)
C140.0344 (9)0.0426 (9)0.0299 (9)0.0029 (8)0.0009 (7)0.0030 (8)
C150.0464 (11)0.0578 (12)0.0349 (11)0.0130 (10)0.0001 (9)0.0104 (10)
C160.0485 (11)0.0586 (13)0.0296 (10)0.0044 (10)0.0013 (8)0.0073 (9)
C170.0358 (9)0.0472 (11)0.0263 (9)0.0029 (8)0.0008 (7)0.0008 (8)
C180.0364 (9)0.0457 (11)0.0369 (10)0.0027 (8)0.0012 (8)0.0000 (8)
C190.0491 (11)0.0435 (11)0.0426 (12)0.0026 (10)0.0060 (9)0.0016 (9)
C17A0.0599 (13)0.0499 (12)0.0374 (11)0.0033 (10)0.0149 (10)0.0074 (9)
C17B0.0533 (13)0.0502 (12)0.0407 (12)0.0032 (10)0.0125 (10)0.0006 (9)
C17C0.0833 (19)0.0662 (16)0.0660 (17)0.0047 (15)0.0422 (16)0.0143 (14)
C17D0.0690 (17)0.0664 (17)0.0763 (19)0.0021 (14)0.0416 (15)0.0076 (15)
C17E0.0490 (13)0.0637 (15)0.0610 (16)0.0037 (11)0.0056 (12)0.0179 (13)
C17F0.0527 (13)0.0563 (13)0.0411 (12)0.0051 (11)0.0016 (10)0.0090 (10)
C17G0.0391 (10)0.0482 (11)0.0297 (10)0.0053 (8)0.0008 (8)0.0061 (8)
Geometric parameters (Å, º) top
O3—C31.428 (3)C11—H11A0.9700
O3—H30.85 (5)C11—H11B0.9700
N17A—C17G1.351 (3)C12—C131.532 (2)
N17A—N17B1.359 (3)C12—H12A0.9700
N17B—C17A1.343 (3)C12—H12B0.9700
N17B—C171.420 (3)C13—C171.520 (2)
C1—C21.528 (3)C13—C181.535 (3)
C1—C101.550 (2)C13—C141.544 (3)
C1—H1A0.9700C14—C151.540 (3)
C1—H1B0.9700C14—H140.9800
C2—C31.509 (4)C15—C161.508 (3)
C2—H2A0.9700C15—H15A0.9700
C2—H2B0.9700C15—H15B0.9700
C3—C41.519 (3)C16—C171.331 (3)
C3—H3A0.9800C16—H160.9300
C4—C51.511 (3)C18—H18A0.9600
C4—H4A0.9700C18—H18B0.9600
C4—H4B0.9700C18—H18C0.9600
C5—C61.325 (3)C19—H19A0.9600
C5—C101.529 (3)C19—H19B0.9600
C6—C71.496 (3)C19—H19C0.9600
C6—H60.9300C17A—C17B1.391 (3)
C7—C81.529 (3)C17A—H17A0.9300
C7—H7A0.9700C17B—C17G1.412 (3)
C7—H7B0.9700C17B—C17C1.421 (3)
C8—C141.520 (3)C17C—C17D1.352 (4)
C8—C91.545 (2)C17C—H17C0.9300
C8—H80.9800C17D—C17E1.401 (4)
C9—C111.546 (3)C17D—H17D0.9300
C9—C101.553 (3)C17E—C17F1.359 (4)
C9—H90.9800C17E—H17E0.9300
C10—C191.540 (3)C17F—C17G1.411 (3)
C11—C121.537 (3)C17F—H17F0.9300
C3—O3—H3109 (3)H11A—C11—H11B107.5
C17G—N17A—N17B103.96 (17)C13—C12—C11110.11 (15)
C17A—N17B—N17A113.45 (17)C13—C12—H12A109.6
C17A—N17B—C17125.50 (19)C11—C12—H12A109.6
N17A—N17B—C17120.69 (16)C13—C12—H12B109.6
C2—C1—C10114.38 (16)C11—C12—H12B109.6
C2—C1—H1A108.7H12A—C12—H12B108.2
C10—C1—H1A108.7C17—C13—C12119.38 (16)
C2—C1—H1B108.7C17—C13—C18107.19 (15)
C10—C1—H1B108.7C12—C13—C18111.61 (17)
H1A—C1—H1B107.6C17—C13—C1498.64 (15)
C3—C2—C1110.9 (2)C12—C13—C14106.97 (15)
C3—C2—H2A109.5C18—C13—C14112.45 (15)
C1—C2—H2A109.5C8—C14—C15121.80 (16)
C3—C2—H2B109.5C8—C14—C13113.28 (16)
C1—C2—H2B109.5C15—C14—C13104.30 (16)
H2A—C2—H2B108.0C8—C14—H14105.4
O3—C3—C2107.8 (2)C15—C14—H14105.4
O3—C3—C4112.6 (2)C13—C14—H14105.4
C2—C3—C4109.90 (18)C16—C15—C14100.90 (17)
O3—C3—H3A108.8C16—C15—H15A111.6
C2—C3—H3A108.8C14—C15—H15A111.6
C4—C3—H3A108.8C16—C15—H15B111.6
C5—C4—C3112.05 (18)C14—C15—H15B111.6
C5—C4—H4A109.2H15A—C15—H15B109.4
C3—C4—H4A109.2C17—C16—C15110.77 (18)
C5—C4—H4B109.2C17—C16—H16124.6
C3—C4—H4B109.2C15—C16—H16124.6
H4A—C4—H4B107.9C16—C17—N17B124.59 (18)
C6—C5—C4121.4 (2)C16—C17—C13111.80 (18)
C6—C5—C10122.59 (19)N17B—C17—C13123.60 (17)
C4—C5—C10116.02 (18)C13—C18—H18A109.5
C5—C6—C7125.6 (2)C13—C18—H18B109.5
C5—C6—H6117.2H18A—C18—H18B109.5
C7—C6—H6117.2C13—C18—H18C109.5
C6—C7—C8112.49 (19)H18A—C18—H18C109.5
C6—C7—H7A109.1H18B—C18—H18C109.5
C8—C7—H7A109.1C10—C19—H19A109.5
C6—C7—H7B109.1C10—C19—H19B109.5
C8—C7—H7B109.1H19A—C19—H19B109.5
H7A—C7—H7B107.8C10—C19—H19C109.5
C14—C8—C7111.86 (18)H19A—C19—H19C109.5
C14—C8—C9108.63 (15)H19B—C19—H19C109.5
C7—C8—C9109.20 (16)N17B—C17A—C17B106.5 (2)
C14—C8—H8109.0N17B—C17A—H17A126.8
C7—C8—H8109.0C17B—C17A—H17A126.8
C9—C8—H8109.0C17A—C17B—C17G104.8 (2)
C8—C9—C11113.51 (15)C17A—C17B—C17C135.7 (2)
C8—C9—C10112.15 (15)C17G—C17B—C17C119.4 (2)
C11—C9—C10112.28 (16)C17D—C17C—C17B118.4 (3)
C8—C9—H9106.1C17D—C17C—H17C120.8
C11—C9—H9106.1C17B—C17C—H17C120.8
C10—C9—H9106.1C17C—C17D—C17E121.6 (2)
C5—C10—C19108.58 (15)C17C—C17D—H17D119.2
C5—C10—C1108.87 (17)C17E—C17D—H17D119.2
C19—C10—C1109.05 (18)C17F—C17E—C17D122.3 (3)
C5—C10—C9109.93 (16)C17F—C17E—H17E118.8
C19—C10—C9112.07 (16)C17D—C17E—H17E118.8
C1—C10—C9108.28 (15)C17E—C17F—C17G117.3 (2)
C12—C11—C9115.00 (18)C17E—C17F—H17F121.4
C12—C11—H11A108.5C17G—C17F—H17F121.4
C9—C11—H11A108.5N17A—C17G—C17F127.6 (2)
C12—C11—H11B108.5N17A—C17G—C17B111.3 (2)
C9—C11—H11B108.5C17F—C17G—C17B121.1 (2)
C17G—N17A—N17B—C17A0.7 (2)C7—C8—C14—C13179.67 (17)
C17G—N17A—N17B—C17172.76 (17)C9—C8—C14—C1359.1 (2)
C10—C1—C2—C356.0 (3)C17—C13—C14—C8170.14 (15)
C1—C2—C3—O3179.14 (19)C12—C13—C14—C865.4 (2)
C1—C2—C3—C457.9 (2)C18—C13—C14—C857.4 (2)
O3—C3—C4—C5176.15 (19)C17—C13—C14—C1535.58 (18)
C2—C3—C4—C556.0 (3)C12—C13—C14—C15159.99 (17)
C3—C4—C5—C6127.6 (2)C18—C13—C14—C1577.14 (19)
C3—C4—C5—C1052.3 (3)C8—C14—C15—C16162.65 (19)
C4—C5—C6—C7178.2 (2)C13—C14—C15—C1633.0 (2)
C10—C5—C6—C71.8 (4)C14—C15—C16—C1717.1 (3)
C5—C6—C7—C813.2 (4)C15—C16—C17—N17B175.08 (19)
C6—C7—C8—C14163.57 (19)C15—C16—C17—C136.2 (3)
C6—C7—C8—C943.3 (3)C17A—N17B—C17—C1623.2 (3)
C14—C8—C9—C1147.4 (2)N17A—N17B—C17—C16164.2 (2)
C7—C8—C9—C11169.67 (19)C17A—N17B—C17—C13158.3 (2)
C14—C8—C9—C10176.00 (16)N17A—N17B—C17—C1314.3 (3)
C7—C8—C9—C1061.8 (2)C12—C13—C17—C16141.6 (2)
C6—C5—C10—C19108.2 (2)C18—C13—C17—C1690.3 (2)
C4—C5—C10—C1971.9 (2)C14—C13—C17—C1626.5 (2)
C6—C5—C10—C1133.2 (2)C12—C13—C17—N17B39.7 (3)
C4—C5—C10—C146.7 (2)C18—C13—C17—N17B88.4 (2)
C6—C5—C10—C914.7 (3)C14—C13—C17—N17B154.80 (18)
C4—C5—C10—C9165.22 (17)N17A—N17B—C17A—C17B0.7 (3)
C2—C1—C10—C548.4 (3)C17—N17B—C17A—C17B172.36 (19)
C2—C1—C10—C1969.9 (3)N17B—C17A—C17B—C17G0.4 (3)
C2—C1—C10—C9167.9 (2)N17B—C17A—C17B—C17C175.5 (3)
C8—C9—C10—C546.2 (2)C17A—C17B—C17C—C17D175.0 (3)
C11—C9—C10—C5175.41 (16)C17G—C17B—C17C—C17D0.5 (4)
C8—C9—C10—C1974.7 (2)C17B—C17C—C17D—C17E0.4 (5)
C11—C9—C10—C1954.6 (2)C17C—C17D—C17E—C17F0.6 (5)
C8—C9—C10—C1165.02 (18)C17D—C17E—C17F—C17G1.4 (4)
C11—C9—C10—C165.8 (2)N17B—N17A—C17G—C17F176.43 (19)
C8—C9—C11—C1246.0 (2)N17B—N17A—C17G—C17B0.4 (2)
C10—C9—C11—C12174.48 (16)C17E—C17F—C17G—N17A175.3 (2)
C9—C11—C12—C1351.4 (2)C17E—C17F—C17G—C17B1.2 (3)
C11—C12—C13—C17168.94 (19)C17A—C17B—C17G—N17A0.0 (3)
C11—C12—C13—C1865.1 (2)C17C—C17B—C17G—N17A176.7 (2)
C11—C12—C13—C1458.3 (2)C17A—C17B—C17G—C17F177.1 (2)
C7—C8—C14—C1554.6 (3)C17C—C17B—C17G—C17F0.3 (4)
C9—C8—C14—C15175.26 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···N17Ai0.85 (5)2.09 (5)2.924 (3)167 (4)
Symmetry code: (i) x+1, y+1/2, z+1.

Experimental details

(I)(II)
Crystal data
Chemical formulaC26H32N2OC26H32N2O
Mr388.54388.54
Crystal system, space groupOrthorhombic, P212121Monoclinic, P21
Temperature (K)293293
a, b, c (Å)6.0445 (1), 12.1149 (2), 28.9321 (4)5.9234 (2), 13.0938 (4), 13.6623 (4)
α, β, γ (°)90, 90, 9090, 91.5347 (16), 90
V3)2118.66 (6)1059.27 (6)
Z42
Radiation typeMo KαMo Kα
µ (mm1)0.070.07
Crystal size (mm)0.22 × 0.15 × 0.030.37 × 0.20 × 0.09
Data collection
DiffractometerBruker APEX CCD area-detector
diffractometer
Bruker APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2000)
Multi-scan
(SADABS; Sheldrick, 2000)
Tmin, Tmax0.915, 0.9980.884, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
48693, 2520, 1985 36122, 2855, 2446
Rint0.0570.032
(sin θ/λ)max1)0.6260.678
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.139, 1.09 0.038, 0.120, 1.08
No. of reflections25202855
No. of parameters267267
No. of restraints01
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.240.23, 0.24

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O3i0.80 (6)2.45 (5)3.233 (4)167 (6)
Symmetry code: (i) x1/2, y+3/2, z+1.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O3—H3···N17Ai0.85 (5)2.09 (5)2.924 (3)167 (4)
Symmetry code: (i) x+1, y+1/2, z+1.
Comparison of the puckering parameters for both compounds top
(I)
RingQ (Å)Q2 (Å)θ (°)ϕ (°)ϕ2 (°)
A0.536 (3)7.0 (3)85 (3)
B0.491 (3)50.7 (4)214.2 (4)
C0.584 (3)13.5 (3)266 (1)
D0.345 (3)214.0 (5)
(II)
A0.540 (2)7.6 (2)96 (2)
B0.496 (2)50.8 (2)212.4 (3)
C0.574 (2)12.4 (2)262 (1)
D0.367 (2)208.0 (4)
 

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