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In the title compound, C23H31N3O3, the outer cyclo­hexane rings have chair conformations, while the central cyclohexene ring adopts a half-chair conformation. In the solid state, intra- and intermolecular C-H...N interactions are observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103028452/sk1690sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103028452/sk1690Isup2.hkl
Contains datablock I

CCDC reference: 233143

Comment top

There are several reports highlighting the fact that steroid molecules containing heteroatoms or fused heterocyclic ring systems exhibit favourable biological activity, such as anti-inflammatory effects (Singh et al., 1991, and references therein; Gupta et al., 1996; Jindal et al., 1996). The present study of the title compound, (I), is part of our ongoing investigation of the crystal structures of a series of androstene derivatives (Thamotharan et al., 2002, and references therein; Hema et al., 2003; Thamotharan et al., 2004). We are interested in the stereochemistry and conformational flexibilities of the steroid nucleus resulting from various substitutions at the C3, C16 and C17 positions. As far as the authors are aware, there seem to be no structures of related androst-5-ene derivatives reported in the literature to date. \sch

The crystals of (I) are enantiomerically pure. However, due to the absence of any significant anomalous scatterers in the compound, the absolute configuration of the molecule has not been determined by the present X-ray diffraction experiment. The enantiomer used in the refinement was assigned to correspond with the configuration of the known chiral centres in a precursor molecule, which remained unchanged during the synthesis of (I).

A perspective view of the molecule (I) with the steroid numbering scheme is shown in Fig. 1. Both methyl groups at C18 and C19 are in the expected staggered arrangement. The geometry at the A/B and B/C ring junctions is quasi-trans and trans, respectively.

In (I), the steroid rings A and C adopt distorted chair and chair conformations, respectively, with puckering parameters (Cremer & Pople, 1975) for ring A of Q = 0.560 (2) Å, q2 = 0.107 (2) Å, q3 = 0.550 (2) Å, θ = 11.0 (2)° and φ2 = 105.4 (12)°, for the atom sequence C1—C5/C10, and for ring C of Q = 0.563 (2) Å, q2 = 0.055 (2) Å, q3 = 0.561 (2) Å, θ = 4.7 (2)° and φ2 = 206 (2)°, for the atom sequence C8—C9—C11—C14. The 3β-acetoxy group is planar. Thus, the presence of an acetoxy group bonded to atom C3 slightly affects the usual chair conformation of ring A of the steroid nucleus. The C3—O20 bond is oriented equatorially and is (-)anticlinal to the C3—C4 bond. In contrast, it lies (-)antiperiplanar to the C3—C4 bond in a related structure with this substitution reported from our laboratory (Thamotharan et al., 2002). The acetoxy group, oxadiazole moiety and nitrile group are oriented nearly perpendicular to the plane of the atoms of steroid rings A/B/C, the dihedral angles being 79.5 (2), 73.6 (1) and 73.6 (1)°, respectively.

The C5C6 (Csp2—Csp2) distance of 1.324 (3) Å confirms the localization of the double bond at this position. This double bond imposes an 8β,9α-half-chair conformation on ring B of the steroid nucleus [the puckering parameters are Q = 0.486 (2) Å, q2 = 0.379 (2) Å, q3 = 0.304 (2) Å, θ = 51.3 (3)° and φ2 = 216.0 (3)°, for the atom sequence C5—C10]. The C9—C10 bond tends to be longer in several derivatives of testosterone. For example, it is 1.590 (7) and 1.580 (8) Å for the two molecules in 8-isotestosterone (Chakrabarti et al., 1981). A slight lengthening is observed in the present structure, the value of this bond being 1.564 (2) Å. The observed lengthening may be attributed to steric strain present at the quaternary atom C10.

The oxadiazole moiety in (I) is in an α-equatorial position, while C15—C16N17 is β-equatorial. Taking C13—C14—C15 as the reference plane, the C18 methyl group and C16 nitrile group are in a syn orientation. The C19—C10···C13—C18 pseudo-torsion angle has a value of 7.02 (17)°, which gives a quantitative measure of the molecular twist.

In the crystalline state of (I), atom C15 is involved in a weak intramolecular C—H···N interaction with atom N25 of the oxadiazole moiety and this interaction leads to an S(6) loop motif (Bernstein et al., 1995). Atom C28 participates in a weak intermolecular C—H···N interaction with atom N25 of an adjacent molecule. This interaction links the steroid molecules into a chain that runs parallel to the a axis and which has a graph-set motif of C(5) (Table 1).

Table 1. Intermolecular C—H···N interactions (Å, °)

Experimental top

A solution of 3β-hydroxy-16-oximino-5-androsten-17-one hydrazone (4 g, 12 mmol) in acetic anhydride (40 ml) was refluxed for 45 min, poured into ice-cold water, filtered, washed, dried and purified by fractional crystallization from ethanol to afford crystals of (I) (institution code DPJ-177) (yield 2 g, 42%; m.p. 501–502 K).

Refinement top

The methyl H atoms were constrained to an ideal geometry (C—H = 0.98 Å), with Uiso(H) = 1.5Ueq(C), but were allowed to rotate freely about the C—C bonds. All remaining H atoms were placed in geometrically idealized positions (C—H = 0.95–1.00 Å) and were constrained to ride on their parent atoms. Due to the absence of any significant anomalous scatterers in (I), attempts to confirm the absolute structure by refinement of the Flack (1983) parameter in the presence of 2812 sets of Friedel equivalents led to an inconclusive value (Flack & Bernardinelli, 2000) of 0.4 (11). Therefore, the Friedel pairs were merged before the final refinement and the absolute configuration was assigned to correspond with that of the known chiral centres in a precursor molecule, which remained unchanged during the synthesis of (I). Reflections 003, 011 and 102 were partially obscured by the beam stop and were omitted.

Structure description top

There are several reports highlighting the fact that steroid molecules containing heteroatoms or fused heterocyclic ring systems exhibit favourable biological activity, such as anti-inflammatory effects (Singh et al., 1991, and references therein; Gupta et al., 1996; Jindal et al., 1996). The present study of the title compound, (I), is part of our ongoing investigation of the crystal structures of a series of androstene derivatives (Thamotharan et al., 2002, and references therein; Hema et al., 2003; Thamotharan et al., 2004). We are interested in the stereochemistry and conformational flexibilities of the steroid nucleus resulting from various substitutions at the C3, C16 and C17 positions. As far as the authors are aware, there seem to be no structures of related androst-5-ene derivatives reported in the literature to date. \sch

The crystals of (I) are enantiomerically pure. However, due to the absence of any significant anomalous scatterers in the compound, the absolute configuration of the molecule has not been determined by the present X-ray diffraction experiment. The enantiomer used in the refinement was assigned to correspond with the configuration of the known chiral centres in a precursor molecule, which remained unchanged during the synthesis of (I).

A perspective view of the molecule (I) with the steroid numbering scheme is shown in Fig. 1. Both methyl groups at C18 and C19 are in the expected staggered arrangement. The geometry at the A/B and B/C ring junctions is quasi-trans and trans, respectively.

In (I), the steroid rings A and C adopt distorted chair and chair conformations, respectively, with puckering parameters (Cremer & Pople, 1975) for ring A of Q = 0.560 (2) Å, q2 = 0.107 (2) Å, q3 = 0.550 (2) Å, θ = 11.0 (2)° and φ2 = 105.4 (12)°, for the atom sequence C1—C5/C10, and for ring C of Q = 0.563 (2) Å, q2 = 0.055 (2) Å, q3 = 0.561 (2) Å, θ = 4.7 (2)° and φ2 = 206 (2)°, for the atom sequence C8—C9—C11—C14. The 3β-acetoxy group is planar. Thus, the presence of an acetoxy group bonded to atom C3 slightly affects the usual chair conformation of ring A of the steroid nucleus. The C3—O20 bond is oriented equatorially and is (-)anticlinal to the C3—C4 bond. In contrast, it lies (-)antiperiplanar to the C3—C4 bond in a related structure with this substitution reported from our laboratory (Thamotharan et al., 2002). The acetoxy group, oxadiazole moiety and nitrile group are oriented nearly perpendicular to the plane of the atoms of steroid rings A/B/C, the dihedral angles being 79.5 (2), 73.6 (1) and 73.6 (1)°, respectively.

The C5C6 (Csp2—Csp2) distance of 1.324 (3) Å confirms the localization of the double bond at this position. This double bond imposes an 8β,9α-half-chair conformation on ring B of the steroid nucleus [the puckering parameters are Q = 0.486 (2) Å, q2 = 0.379 (2) Å, q3 = 0.304 (2) Å, θ = 51.3 (3)° and φ2 = 216.0 (3)°, for the atom sequence C5—C10]. The C9—C10 bond tends to be longer in several derivatives of testosterone. For example, it is 1.590 (7) and 1.580 (8) Å for the two molecules in 8-isotestosterone (Chakrabarti et al., 1981). A slight lengthening is observed in the present structure, the value of this bond being 1.564 (2) Å. The observed lengthening may be attributed to steric strain present at the quaternary atom C10.

The oxadiazole moiety in (I) is in an α-equatorial position, while C15—C16N17 is β-equatorial. Taking C13—C14—C15 as the reference plane, the C18 methyl group and C16 nitrile group are in a syn orientation. The C19—C10···C13—C18 pseudo-torsion angle has a value of 7.02 (17)°, which gives a quantitative measure of the molecular twist.

In the crystalline state of (I), atom C15 is involved in a weak intramolecular C—H···N interaction with atom N25 of the oxadiazole moiety and this interaction leads to an S(6) loop motif (Bernstein et al., 1995). Atom C28 participates in a weak intermolecular C—H···N interaction with atom N25 of an adjacent molecule. This interaction links the steroid molecules into a chain that runs parallel to the a axis and which has a graph-set motif of C(5) (Table 1).

Table 1. Intermolecular C—H···N interactions (Å, °)

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented by circles of arbitrary radii.
16-Cyano-3α-(5-methyl-1,3,4-oxadiazol-2-yl)-13,16-seco-17-norandrost- 5-en-3β-yl acetate top
Crystal data top
C23H31N3O3F(000) = 428
Mr = 397.51Dx = 1.255 Mg m3
Monoclinic, P21Melting point: 501 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 6.1855 (1) ÅCell parameters from 3282 reflections
b = 7.5511 (1) Åθ = 2.0–30.0°
c = 22.6406 (4) ŵ = 0.08 mm1
β = 95.9439 (10)°T = 160 K
V = 1051.80 (3) Å3Prism, colourless
Z = 20.30 × 0.28 × 0.20 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
2778 reflections with I > 2σ(I)
Radiation source: Nonius FR591 sealed tube generatorRint = 0.046
Horizontally mounted graphite crystal monochromatorθmax = 30.0°, θmin = 3.3°
Detector resolution: 9 pixels mm-1h = 88
φ and ω scans with κ offsetsk = 1010
27570 measured reflectionsl = 3131
3279 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0511P)2 + 0.1624P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3276 reflectionsΔρmax = 0.24 e Å3
267 parametersΔρmin = 0.23 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.026 (5)
Crystal data top
C23H31N3O3V = 1051.80 (3) Å3
Mr = 397.51Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.1855 (1) ŵ = 0.08 mm1
b = 7.5511 (1) ÅT = 160 K
c = 22.6406 (4) Å0.30 × 0.28 × 0.20 mm
β = 95.9439 (10)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
2778 reflections with I > 2σ(I)
27570 measured reflectionsRint = 0.046
3279 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0431 restraint
wR(F2) = 0.108H-atom parameters constrained
S = 1.05Δρmax = 0.24 e Å3
3276 reflectionsΔρmin = 0.23 e Å3
267 parameters
Special details top

Experimental. Solvent used: acetone Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.419 (1) Frames collected: 597 Seconds exposure per frame: 17 Degrees rotation per frame: 1.4 Crystal-Detector distance (mm): 33.80

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
O200.7192 (2)0.7510 (2)0.00274 (5)0.0307 (3)
O211.0737 (3)0.8135 (4)0.00479 (7)0.0704 (8)
O230.7870 (2)0.6753 (2)0.45148 (6)0.0329 (3)
N170.1172 (3)0.2107 (3)0.31234 (10)0.0478 (5)
N250.4838 (3)0.5614 (3)0.47730 (7)0.0359 (4)
N260.6412 (3)0.5634 (3)0.52778 (7)0.0360 (4)
C10.6515 (4)0.8938 (3)0.15431 (8)0.0301 (4)
H1A0.59371.00410.17030.036*
H1B0.80540.88270.17090.036*
C20.6429 (4)0.9110 (3)0.08648 (9)0.0309 (5)
H2A0.49170.93420.06930.037*
H2B0.73491.01120.07610.037*
C30.7239 (3)0.7407 (3)0.06163 (8)0.0282 (4)
H30.87580.71700.07950.034*
C40.5786 (3)0.5884 (3)0.07514 (8)0.0276 (4)
H4A0.63180.47750.05840.033*
H4B0.42880.61030.05670.033*
C50.5783 (3)0.5699 (3)0.14187 (8)0.0245 (4)
C60.6234 (3)0.4153 (3)0.16783 (9)0.0280 (4)
H60.66130.32050.14330.034*
C70.6195 (4)0.3776 (3)0.23258 (9)0.0315 (4)
H7A0.77030.35890.25080.038*
H7B0.53760.26660.23720.038*
C80.5160 (3)0.5263 (2)0.26557 (8)0.0235 (4)
H80.35460.51810.25640.028*
C90.5900 (3)0.7070 (2)0.24390 (8)0.0238 (4)
H90.75250.70720.24960.029*
C100.5226 (3)0.7345 (3)0.17601 (8)0.0235 (4)
C110.5143 (4)0.8580 (3)0.28173 (8)0.0320 (5)
H11A0.57790.97060.26930.038*
H11B0.35420.86830.27470.038*
C120.5800 (4)0.8287 (3)0.34791 (9)0.0313 (5)
H12A0.52700.92920.37050.038*
H12B0.74060.82640.35530.038*
C130.4883 (3)0.6553 (3)0.37047 (8)0.0267 (4)
C140.5717 (3)0.5015 (3)0.33298 (8)0.0234 (4)
H140.73390.50550.34010.028*
C150.5050 (3)0.3158 (3)0.35370 (8)0.0283 (4)
H15A0.61140.22820.34180.034*
H15B0.51410.31550.39760.034*
C160.2865 (3)0.2584 (3)0.33025 (9)0.0335 (4)
C180.2388 (3)0.6622 (3)0.36805 (9)0.0353 (5)
H18A0.18600.55490.38620.053*
H18B0.17590.66990.32660.053*
H18C0.19580.76640.38980.053*
C190.2774 (3)0.7709 (3)0.16270 (9)0.0330 (5)
H19A0.23950.77780.11960.049*
H19B0.24150.88330.18100.049*
H19C0.19510.67480.17900.049*
C210.9064 (3)0.7815 (3)0.02480 (9)0.0345 (5)
C220.8805 (4)0.7718 (4)0.09128 (9)0.0407 (5)
H22A1.00260.83250.10690.061*
H22B0.74400.82900.10660.061*
H22C0.87820.64740.10380.061*
C240.5763 (3)0.6295 (3)0.43444 (8)0.0267 (4)
C270.8126 (3)0.6313 (3)0.51027 (8)0.0332 (5)
C281.0251 (4)0.6661 (5)0.54410 (10)0.0481 (6)
H28A1.04350.79390.55020.072*
H28B1.14130.62110.52190.072*
H28C1.03160.60640.58270.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O200.0275 (6)0.0442 (9)0.0207 (6)0.0001 (7)0.0042 (5)0.0038 (6)
O210.0354 (9)0.136 (2)0.0390 (9)0.0266 (12)0.0014 (8)0.0176 (12)
O230.0337 (7)0.0445 (9)0.0210 (6)0.0036 (7)0.0054 (5)0.0032 (6)
N170.0453 (11)0.0457 (13)0.0511 (12)0.0086 (10)0.0010 (9)0.0079 (10)
N250.0407 (9)0.0442 (11)0.0235 (8)0.0028 (9)0.0065 (7)0.0027 (8)
N260.0426 (10)0.0438 (11)0.0218 (8)0.0005 (9)0.0050 (7)0.0018 (8)
C10.0438 (11)0.0261 (10)0.0207 (9)0.0053 (9)0.0044 (8)0.0005 (8)
C20.0416 (11)0.0258 (11)0.0254 (10)0.0067 (9)0.0044 (8)0.0024 (8)
C30.0283 (9)0.0370 (11)0.0192 (8)0.0017 (8)0.0026 (7)0.0030 (8)
C40.0342 (10)0.0281 (10)0.0208 (8)0.0002 (8)0.0037 (7)0.0017 (8)
C50.0261 (8)0.0247 (9)0.0228 (8)0.0025 (8)0.0031 (7)0.0013 (8)
C60.0363 (10)0.0255 (10)0.0230 (9)0.0024 (8)0.0066 (8)0.0032 (7)
C70.0465 (12)0.0227 (9)0.0261 (9)0.0077 (9)0.0072 (9)0.0029 (8)
C80.0290 (9)0.0209 (9)0.0207 (8)0.0023 (7)0.0029 (7)0.0007 (7)
C90.0294 (9)0.0220 (9)0.0200 (8)0.0001 (7)0.0031 (7)0.0006 (7)
C100.0280 (8)0.0223 (9)0.0202 (8)0.0004 (7)0.0021 (7)0.0014 (7)
C110.0519 (13)0.0216 (10)0.0228 (9)0.0049 (9)0.0057 (9)0.0014 (8)
C120.0506 (12)0.0227 (10)0.0211 (9)0.0008 (9)0.0051 (8)0.0008 (8)
C130.0330 (10)0.0262 (10)0.0211 (8)0.0025 (8)0.0040 (7)0.0004 (8)
C140.0265 (8)0.0231 (9)0.0207 (8)0.0007 (7)0.0035 (7)0.0011 (7)
C150.0363 (10)0.0241 (10)0.0244 (9)0.0008 (8)0.0026 (8)0.0023 (8)
C160.0412 (11)0.0289 (11)0.0308 (10)0.0020 (10)0.0055 (9)0.0048 (9)
C180.0339 (10)0.0397 (12)0.0328 (10)0.0096 (10)0.0056 (8)0.0006 (10)
C190.0291 (9)0.0414 (12)0.0283 (9)0.0048 (9)0.0022 (7)0.0010 (9)
C210.0299 (10)0.0438 (13)0.0307 (10)0.0004 (9)0.0068 (8)0.0077 (10)
C220.0375 (10)0.0571 (15)0.0285 (9)0.0090 (11)0.0084 (8)0.0068 (11)
C240.0306 (9)0.0251 (10)0.0249 (9)0.0014 (8)0.0055 (8)0.0008 (8)
C270.0389 (11)0.0409 (13)0.0203 (9)0.0031 (10)0.0058 (8)0.0003 (9)
C280.0412 (12)0.0739 (19)0.0287 (10)0.0024 (13)0.0010 (9)0.0014 (12)
Geometric parameters (Å, º) top
O20—C211.328 (2)C9—C101.564 (2)
O20—C31.457 (2)C9—H91.0000
O21—C211.198 (3)C10—C191.540 (3)
O23—C241.365 (2)C11—C121.527 (3)
O23—C271.365 (2)C11—H11A0.9900
N17—C161.142 (3)C11—H11B0.9900
N25—C241.284 (3)C12—C131.535 (3)
N25—N261.423 (2)C12—H12A0.9900
N26—C271.277 (3)C12—H12B0.9900
C1—C21.536 (3)C13—C241.506 (3)
C1—C101.551 (3)C13—C181.539 (3)
C1—H1A0.9900C13—C141.557 (3)
C1—H1B0.9900C14—C151.548 (3)
C2—C31.510 (3)C14—H141.0000
C2—H2A0.9900C15—C161.465 (3)
C2—H2B0.9900C15—H15A0.9900
C3—C41.510 (3)C15—H15B0.9900
C3—H31.0000C18—H18A0.9800
C4—C51.517 (2)C18—H18B0.9800
C4—H4A0.9900C18—H18C0.9800
C4—H4B0.9900C19—H19A0.9800
C5—C61.324 (3)C19—H19B0.9800
C5—C101.522 (3)C19—H19C0.9800
C6—C71.496 (3)C21—C221.499 (3)
C6—H60.9500C22—H22A0.9800
C7—C81.526 (3)C22—H22B0.9800
C7—H7A0.9900C22—H22C0.9800
C7—H7B0.9900C27—C281.475 (3)
C8—C91.536 (3)C28—H28A0.9800
C8—C141.541 (2)C28—H28B0.9800
C8—H81.0000C28—H28C0.9800
C9—C111.528 (3)
C21—O20—C3117.23 (14)C12—C11—H11B109.2
C24—O23—C27102.98 (15)C9—C11—H11B109.2
C24—N25—N26106.34 (18)H11A—C11—H11B107.9
C27—N26—N25106.02 (16)C11—C12—C13112.31 (17)
C2—C1—C10114.58 (16)C11—C12—H12A109.1
C2—C1—H1A108.6C13—C12—H12A109.1
C10—C1—H1A108.6C11—C12—H12B109.1
C2—C1—H1B108.6C13—C12—H12B109.1
C10—C1—H1B108.6H12A—C12—H12B107.9
H1A—C1—H1B107.6C24—C13—C12108.73 (16)
C3—C2—C1108.80 (16)C24—C13—C18107.43 (15)
C3—C2—H2A109.9C12—C13—C18111.25 (17)
C1—C2—H2A109.9C24—C13—C14108.70 (16)
C3—C2—H2B109.9C12—C13—C14107.48 (14)
C1—C2—H2B109.9C18—C13—C14113.16 (17)
H2A—C2—H2B108.3C8—C14—C15111.79 (15)
O20—C3—C2110.76 (16)C8—C14—C13113.35 (15)
O20—C3—C4107.02 (15)C15—C14—C13113.37 (15)
C2—C3—C4110.20 (15)C8—C14—H14105.8
O20—C3—H3109.6C15—C14—H14105.8
C2—C3—H3109.6C13—C14—H14105.8
C4—C3—H3109.6C16—C15—C14115.01 (17)
C3—C4—C5109.51 (15)C16—C15—H15A108.5
C3—C4—H4A109.8C14—C15—H15A108.5
C5—C4—H4A109.8C16—C15—H15B108.5
C3—C4—H4B109.8C14—C15—H15B108.5
C5—C4—H4B109.8H15A—C15—H15B107.5
H4A—C4—H4B108.2N17—C16—C15178.8 (3)
C6—C5—C4120.10 (18)C13—C18—H18A109.5
C6—C5—C10122.89 (16)C13—C18—H18B109.5
C4—C5—C10117.00 (16)H18A—C18—H18B109.5
C5—C6—C7125.40 (18)C13—C18—H18C109.5
C5—C6—H6117.3H18A—C18—H18C109.5
C7—C6—H6117.3H18B—C18—H18C109.5
C6—C7—C8112.92 (16)C10—C19—H19A109.5
C6—C7—H7A109.0C10—C19—H19B109.5
C8—C7—H7A109.0H19A—C19—H19B109.5
C6—C7—H7B109.0C10—C19—H19C109.5
C8—C7—H7B109.0H19A—C19—H19C109.5
H7A—C7—H7B107.8H19B—C19—H19C109.5
C7—C8—C9110.09 (15)O21—C21—O20124.16 (19)
C7—C8—C14109.47 (15)O21—C21—C22124.59 (18)
C9—C8—C14112.40 (15)O20—C21—C22111.25 (17)
C7—C8—H8108.3C21—C22—H22A109.5
C9—C8—H8108.3C21—C22—H22B109.5
C14—C8—H8108.3H22A—C22—H22B109.5
C11—C9—C8111.41 (14)C21—C22—H22C109.5
C11—C9—C10112.70 (15)H22A—C22—H22C109.5
C8—C9—C10111.95 (15)H22B—C22—H22C109.5
C11—C9—H9106.8N25—C24—O23112.04 (17)
C8—C9—H9106.8N25—C24—C13129.32 (18)
C10—C9—H9106.8O23—C24—C13118.57 (16)
C5—C10—C19108.47 (16)N26—C27—O23112.61 (18)
C5—C10—C1108.76 (15)N26—C27—C28129.35 (19)
C19—C10—C1109.13 (17)O23—C27—C28118.04 (18)
C5—C10—C9109.85 (15)C27—C28—H28A109.5
C19—C10—C9111.88 (15)C27—C28—H28B109.5
C1—C10—C9108.70 (14)H28A—C28—H28B109.5
C12—C11—C9112.10 (16)C27—C28—H28C109.5
C12—C11—H11A109.2H28A—C28—H28C109.5
C9—C11—H11A109.2H28B—C28—H28C109.5
C24—N25—N26—C270.4 (2)C8—C9—C11—C1252.8 (2)
C10—C1—C2—C356.5 (2)C10—C9—C11—C12179.64 (16)
C21—O20—C3—C2101.5 (2)C9—C11—C12—C1358.5 (2)
C21—O20—C3—C4138.30 (19)C11—C12—C13—C24175.21 (17)
C1—C2—C3—O20179.83 (15)C11—C12—C13—C1866.7 (2)
C1—C2—C3—C461.9 (2)C11—C12—C13—C1457.7 (2)
O20—C3—C4—C5179.51 (15)C7—C8—C14—C1554.9 (2)
C2—C3—C4—C560.0 (2)C9—C8—C14—C15177.56 (15)
C3—C4—C5—C6127.1 (2)C7—C8—C14—C13175.47 (16)
C3—C4—C5—C1053.5 (2)C9—C8—C14—C1352.8 (2)
C4—C5—C6—C7177.30 (19)C24—C13—C14—C8172.70 (15)
C10—C5—C6—C72.1 (3)C12—C13—C14—C855.2 (2)
C5—C6—C7—C811.0 (3)C18—C13—C14—C868.0 (2)
C6—C7—C8—C941.1 (2)C24—C13—C14—C1558.5 (2)
C6—C7—C8—C14165.15 (16)C12—C13—C14—C15175.98 (16)
C7—C8—C9—C11172.30 (17)C18—C13—C14—C1560.8 (2)
C14—C8—C9—C1150.0 (2)C8—C14—C15—C1646.2 (2)
C7—C8—C9—C1060.47 (19)C13—C14—C15—C1683.5 (2)
C14—C8—C9—C10177.21 (15)C3—O20—C21—O215.7 (4)
C6—C5—C10—C19106.8 (2)C3—O20—C21—C22174.7 (2)
C4—C5—C10—C1972.6 (2)N26—N25—C24—O231.1 (2)
C6—C5—C10—C1134.63 (19)N26—N25—C24—C13178.0 (2)
C4—C5—C10—C146.0 (2)C27—O23—C24—N251.3 (2)
C6—C5—C10—C915.8 (3)C27—O23—C24—C13178.57 (18)
C4—C5—C10—C9164.82 (15)C12—C13—C24—N25144.7 (2)
C2—C1—C10—C547.1 (2)C18—C13—C24—N2524.2 (3)
C2—C1—C10—C1971.1 (2)C14—C13—C24—N2598.5 (2)
C2—C1—C10—C9166.66 (17)C12—C13—C24—O2338.5 (2)
C11—C9—C10—C5173.11 (16)C18—C13—C24—O23159.03 (18)
C8—C9—C10—C546.59 (19)C14—C13—C24—O2378.2 (2)
C11—C9—C10—C1952.6 (2)N25—N26—C27—O230.5 (3)
C8—C9—C10—C1973.9 (2)N25—N26—C27—C28179.7 (3)
C11—C9—C10—C168.0 (2)C24—O23—C27—N261.1 (2)
C8—C9—C10—C1165.48 (16)C24—O23—C27—C28179.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15B···N250.992.613.371 (3)134
C28—H28B···N25i0.982.483.443 (3)167
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC23H31N3O3
Mr397.51
Crystal system, space groupMonoclinic, P21
Temperature (K)160
a, b, c (Å)6.1855 (1), 7.5511 (1), 22.6406 (4)
β (°) 95.9439 (10)
V3)1051.80 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.30 × 0.28 × 0.20
Data collection
DiffractometerNonius KappaCCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
27570, 3279, 2778
Rint0.046
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.108, 1.05
No. of reflections3276
No. of parameters267
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.23

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15B···N250.992.613.371 (3)134
C28—H28B···N25i0.982.483.443 (3)167
Symmetry code: (i) x+1, y, z.
 

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