Download citation
Download citation
link to html
In the title compound, C29H36O2, the outer cyclohexene ring of the steroid nucleus has a conformation that lies about half-way between a half-chair and an envelope, while the central and outer cyclo­hexane rings of the steroid nucleus have slightly distorted chair conformations. The steroidal cyclo­pentane ring adopts a 13[beta],14[alpha]-half-chair conformation. The benzyl­idene moiety has an E configuration with respect to the carbonyl group on the cyclo­pentane ring. The dihedral angle between the mean planes of the steroid nucleus and the benzyl­idene moiety is 35.54 (9)°. The packing of the mol­ecules is assumed to be dictated mainly by weak intermolecular C-H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103028038/sk1688sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103028038/sk1688Isup2.hkl
Contains datablock I

CCDC reference: 233124

Comment top

The present study 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., 2003). We are particularly interested in studying the conformational flexibilities of the steroid nucleus resulting from various substitutions at the C3, C16 and C17 positions. The crystals of the title compound, (I), are enantiomerically pure; however, because of the absence of any significant anomalous scatterers in the compound, the absolute configuration of the molecule has not been determined from the X-ray diffraction experiment and the assumed chirality of the molecule was determined from the route of synthesis.

Both methyl groups of the steroid nucleus adopt the expected staggered arrangements. The B/C and C/D ring junctions are all-trans (see scheme and Fig. 1). In (I), the tetrahydropyridine ring, A, has a conformation that lies about half way between that of a half-chair and an envelope [puckering parameters (Cremer & Pople, 1975) Q = 0.454 (3) Å, q2 = 0.360 (3) Å, q3 = 0.277 (3) Å, θ = 52.4 (4)° and ϕ2 = 12.7 (5)° for the atom sequence C1—C2—C3—C4—C5—C10]. Distorted half-chair conformations have been reported for the conformation of ring A in the two related structures androst-4-ene-3,17-dione (Busetta et al., 1972) and 16-(3-pyridylmethylene)androst-4-ene-3,17-dione (Vasuki, Thamotharan et al., 2002), while an envelope conformation has been reported in another related compound (Vasuki, Parthasarathi et al., 2002). The C4C5 (Csp2—Csp2) distance of 1.338 (4) Å confirms the localization of a double bond at this position.

The steroidal cyclohexane rings, B and C, are in slightly distorted chair conformations, as shown by their puckering parameters [ring B: Q = 0.534 (3) Å, q2 = 0.084 (3) Å, q3 = 0.528 (3) Å, θ = 8.9 (3)° and ϕ2 = 146.1 (19)° for the atom sequence C5—C6—C7—C8—C9—C10; ring C: Q = 0.584 (3) Å, q2 = 0.046 (3) Å, q3 = 0.582 (3) Å, θ = 4.3 (3)° and ϕ2 = 282 (3)° for the atom sequence C8—C9—C11—C12—C13—C14]. The cyclopentane ring, D, of the steroid nucleus adopts a 13β,14α-half-chair conformation, with a pseudo-rotation angle of 6.5 (2)° and a maximum torsion angle of 43.2 (1)° (Rao et al., 1981) for the atom sequence C13—C14—C15—C16—C17. In a related structure, in which atom C16 has no substitution, ring D has a 14α-envelope conformation (Busetta et al., 1972).

The C3···C16 distance of 8.849 (4) Å, which is a measure of the length of the steroid nucleus, indicates that the steroid nucleus is in a completely extended form (Karle, 1970). The distance between terminal atoms O3 and C27A is 14.330 (4) Å. The C19—C10···C13—C18 pseudo-torsion angle, which gives a measure of the molecular twist, is 9.0 (2)°. The value of the C17—C16—C20—C21 torsion angle [−176.6 (3)°] indicates that the benzylidene ring has an E configuration with respect to the carbonyl group at position C17. The C15—C16—C20 exocyclic angle [131.2 (2)°] is slightly larger than the normal value, possibly as a consequence of steric repulsion between atoms H15B and H26 (H···H = 2.26 Å). The dihedral angle between the mean planes of the steroid nucleus and the benzylidene moiety is 35.54 (9)°. In (I), the skeletal bond angles are close to the expected values (Duax et al., 1976). Additionally, the isopropyl group is disordered over two orientations, with the major conformation existing in 59.5 (7)% of the molecules.

In (I), atom C1 acts as a donor for a weak intermolecular C—H···O interaction with carbonyl atom O17 of an adjacent molecule. This interaction links the molecules into a chain that runs parallel to the y axis and has a graph-set motif of C(9) (Bernstein et al., 1995). One of the disordered methyl atoms (C28A) of an isopropyl group is involved in an intermolecular C—H···O interaction with the other carbonyl O atom (O3) of a different adjacent molecule. This interaction links the molecules into a chain, which also runs parallel to the y axis and has a graph-set motif of C(18) (Table 1).

Experimental top

16-(4-Isopropylbenzylidene)-17-oxo-5-androsten-3β-ol (1.0 g) was dissolved in dry toluene (150 ml) by refluxing, and then cyclohexanone (10 ml) was added. Traces of moisture were removed by azeotropic distillation. The distillation was continued at a slow rate while adding a solution of aluminium isopropoxide (1.0 g) in dry toluene (15 ml) dropwise. The reaction mixture was refluxed for 4 h and then allowed to stand overnight at room temperature. The slurry was filtered and the residue was washed thoroughly with dry toluene. The combined filtrate and washings were steam distilled until the complete removal of organic solvents was affected. The solid residue was collected by filtration the next day, dried and crystallized from acetone at a cold temperature to afford crystals of (I) (yield 0.80 g, 80.39%; m.p. 453–459 K). UVmax(MeOH):305.6 nm (logε = 4.48) and 233.6 nm (logε = 4.36); IRmax (cm−1): 2975,1705,1690,1600, 900; 1H NMR (CDCl3): 1.01 (s,3H,18-CH3), 1.25 (s,3H,19-CH3), 1.26 [d,6H,CH-(CH3)2], 2.91 [m,1H, CH-(CH3)2], 5.76 (s,1H,4-CH), 7.44 [s,1H,vinyl-H of 16-(4-isopropylbenzylidene)],7.27–7.30 (d,2H,Jo=8.2, 3-CH and 5-CH aromatic proton) and 7.47–7.49 (d,2H,Jo=8.2,2-CH and 6-CH aromatic proton).

Refinement top

The isopropyl group is disordered over two sites. Two sets of positions were defined for all atoms of this group, and constrained refinement of the site-occupation factors led to a value of 0.595 (7) for the major conformation. Similarity restraints were applied to all 1,2 and 1,3 distances involving disordered atoms, so as to maintain similar geometry about the chemically equivalent atoms. This treatment led to non-ideal angles about atom C24, and it is likely that the disorder extends into the phenyl ring, particularly as atoms C23, C24 and C25 show slightly elongated atomic displacement ellipsoids. However, attempts to model disorder for the ring, even by employing extensive restraints, proved fruitless. Methyl H atoms were constrained to an ideal geometry (C—H = 0.98 Å), with Uiso(H) values of 1.5Uiso(C), but were allowed to rotate freely about the C—C bonds. All remaining H atoms were placed in idealized positions (C—H = 0.95–1.00 Å) and constrained to ride on their parent non-H atoms, with Uiso(H) values of 1.2Uiso(C). Because of 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 1757 sets of Friedel equivalents led to an inconclusive value of −0.1 (19) (Flack & Bernardinelli, 2000). Therefore, the Friedel pairs were merged before the final refinement and the absolute configuration was assigned to correspond with the known chiral centers in a precursor molecule, which remained unchanged during the synthesis of (I). Reflection 020 was partially obscured by the beam stop and was omitted.

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 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. A perspective view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. For clarity, all H atoms of the disordered isopropyl moiety have been omitted. The other H atoms are shown as small circles of arbitrary radii.
16-(4-isopropylbenzylidene)androst-4-ene-3,17-dione top
Crystal data top
C29H36O2Dx = 1.162 Mg m3
Mr = 416.58Melting point: 453 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2447 reflections
a = 6.1318 (2) Åθ = 2.0–25.0°
b = 17.3938 (5) ŵ = 0.07 mm1
c = 22.3210 (7) ÅT = 160 K
V = 2380.65 (13) Å3Prism, colourless
Z = 40.25 × 0.20 × 0.18 mm
F(000) = 904
Data collection top
Nonius KappaCCD
diffractometer
2000 reflections with I > 2σ(I)
Radiation source: Nonius FR591 sealed tube generatorRint = 0.055
Horizontally mounted graphite crystal monochromatorθmax = 25.0°, θmin = 2.2°
Detector resolution: 9 pixels mm-1h = 77
ϕ and ω scans with κ offsetsk = 2020
22900 measured reflectionsl = 2626
2437 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)] = 0.045H-atom parameters constrained
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.0635P)2 + 0.3105P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2436 reflectionsΔρmax = 0.16 e Å3
315 parametersΔρmin = 0.16 e Å3
87 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.028 (5)
Crystal data top
C29H36O2V = 2380.65 (13) Å3
Mr = 416.58Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.1318 (2) ŵ = 0.07 mm1
b = 17.3938 (5) ÅT = 160 K
c = 22.3210 (7) Å0.25 × 0.20 × 0.18 mm
Data collection top
Nonius KappaCCD
diffractometer
2000 reflections with I > 2σ(I)
22900 measured reflectionsRint = 0.055
2437 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04587 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.04Δρmax = 0.16 e Å3
2436 reflectionsΔρmin = 0.16 e Å3
315 parameters
Special details top

Experimental. Solvent used: acetone Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.795 (2) Frames collected: 178 Seconds exposure per frame: 160 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 33.50

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*/UeqOcc. (<1)
O30.8311 (5)0.43387 (13)0.98218 (11)0.1005 (9)
O170.4063 (3)0.07589 (10)0.76056 (9)0.0647 (6)
C10.6333 (5)0.31625 (14)0.86174 (14)0.0601 (8)
H1A0.55460.32370.82350.072*
H1B0.53040.29280.89060.072*
C20.7051 (6)0.39418 (15)0.88540 (15)0.0707 (9)
H2A0.79520.42040.85480.085*
H2B0.57500.42640.89310.085*
C30.8328 (6)0.38589 (16)0.94154 (16)0.0738 (10)
C40.9711 (5)0.31658 (16)0.94656 (13)0.0642 (8)
H41.06420.31210.98040.077*
C50.9723 (5)0.25985 (14)0.90607 (12)0.0510 (7)
C61.1315 (5)0.19481 (14)0.91120 (13)0.0560 (7)
H6A1.20340.19710.95090.067*
H6B1.24560.20080.88020.067*
C71.0226 (5)0.11673 (14)0.90384 (12)0.0508 (7)
H7A0.91960.10790.93730.061*
H7B1.13450.07570.90500.061*
C80.9003 (4)0.11343 (13)0.84446 (11)0.0413 (6)
H81.00700.12000.81100.050*
C90.7294 (4)0.17795 (13)0.84093 (11)0.0419 (6)
H90.62550.16850.87470.050*
C100.8252 (4)0.26053 (14)0.85143 (11)0.0470 (6)
C110.5931 (4)0.17255 (14)0.78302 (11)0.0500 (7)
H11A0.47700.21210.78420.060*
H11B0.68820.18390.74830.060*
C120.4881 (4)0.09326 (14)0.77409 (12)0.0510 (7)
H12A0.37820.08430.80580.061*
H12B0.41280.09170.73490.061*
C130.6597 (4)0.03060 (14)0.77643 (10)0.0445 (6)
C140.7827 (4)0.03708 (13)0.83663 (10)0.0400 (6)
H140.66750.03600.86830.048*
C150.9050 (4)0.03997 (13)0.84223 (11)0.0475 (6)
H15A1.04140.03980.81850.057*
H15B0.93950.05200.88450.057*
C160.7404 (4)0.09594 (13)0.81681 (11)0.0449 (6)
C170.5769 (5)0.05124 (15)0.78141 (11)0.0495 (7)
C180.8125 (5)0.03251 (17)0.72169 (11)0.0615 (8)
H18A0.72800.02250.68520.092*
H18B0.92530.00700.72620.092*
H18C0.88140.08320.71880.092*
C190.9624 (5)0.28727 (15)0.79738 (12)0.0548 (7)
H19A1.04260.33400.80810.082*
H19B0.86580.29800.76340.082*
H19C1.06580.24670.78630.082*
C200.7178 (5)0.17195 (14)0.82416 (11)0.0521 (7)
H200.59740.19400.80360.062*
C210.8478 (5)0.22632 (15)0.85861 (12)0.0539 (7)
C220.7584 (6)0.29894 (15)0.86985 (13)0.0691 (9)
H220.62140.31240.85300.083*
C230.8697 (8)0.35152 (17)0.90571 (16)0.0848 (12)
H230.80610.40050.91280.102*
C251.1586 (7)0.2650 (2)0.91720 (18)0.0957 (12)
H251.29900.25280.93250.115*
C261.0519 (5)0.21146 (17)0.88149 (16)0.0742 (10)
H261.12090.16390.87270.089*
C27A1.1994 (10)0.3797 (3)0.9791 (2)0.0764 (19)0.595 (7)
H27A1.32070.34730.99510.092*0.595 (7)
C28A1.038 (2)0.4004 (9)1.0292 (4)0.092 (3)0.595 (7)
H28A0.91060.42641.01180.139*0.595 (7)
H28B0.99030.35341.04960.139*0.595 (7)
H28C1.10880.43471.05800.139*0.595 (7)
C29A1.2902 (12)0.4526 (3)0.9492 (3)0.0796 (19)0.595 (7)
H29A1.37060.48300.97880.119*0.595 (7)
H29B1.38840.43810.91640.119*0.595 (7)
H29C1.16940.48330.93320.119*0.595 (7)
C241.0680 (7)0.3350 (2)0.93111 (17)0.0884 (12)
C27B1.1383 (11)0.4110 (3)0.9606 (3)0.070 (2)0.405 (7)
H27B1.07950.45670.93880.084*0.405 (7)
C28B1.059 (3)0.4082 (10)1.0260 (5)0.077 (4)0.405 (7)
H28D1.11580.36191.04550.115*0.405 (7)
H28E1.11070.45381.04740.115*0.405 (7)
H28F0.89890.40711.02680.115*0.405 (7)
C29B1.3895 (12)0.4086 (5)0.9592 (4)0.082 (3)0.405 (7)
H29D1.43930.40130.91790.123*0.405 (7)
H29E1.44760.45710.97490.123*0.405 (7)
H29F1.44130.36590.98410.123*0.405 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.132 (2)0.0666 (14)0.1028 (18)0.0226 (15)0.0430 (18)0.0298 (13)
O170.0630 (13)0.0564 (11)0.0746 (13)0.0030 (11)0.0201 (11)0.0046 (10)
C10.0575 (17)0.0400 (14)0.0828 (19)0.0055 (14)0.0197 (16)0.0012 (13)
C20.075 (2)0.0462 (15)0.091 (2)0.0007 (16)0.023 (2)0.0025 (15)
C30.086 (2)0.0479 (16)0.087 (2)0.0205 (17)0.038 (2)0.0115 (16)
C40.071 (2)0.0607 (17)0.0608 (17)0.0191 (17)0.0134 (16)0.0030 (14)
C50.0552 (16)0.0445 (14)0.0534 (15)0.0124 (13)0.0127 (14)0.0059 (12)
C60.0548 (16)0.0532 (15)0.0599 (16)0.0102 (14)0.0093 (14)0.0079 (13)
C70.0497 (15)0.0476 (14)0.0552 (15)0.0033 (13)0.0083 (13)0.0086 (12)
C80.0381 (12)0.0404 (13)0.0453 (13)0.0056 (11)0.0016 (11)0.0043 (10)
C90.0402 (13)0.0383 (12)0.0472 (13)0.0036 (11)0.0042 (11)0.0044 (10)
C100.0450 (14)0.0426 (13)0.0535 (15)0.0000 (12)0.0094 (13)0.0052 (11)
C110.0461 (14)0.0461 (14)0.0579 (15)0.0111 (13)0.0046 (14)0.0089 (12)
C120.0469 (14)0.0503 (15)0.0558 (15)0.0066 (13)0.0103 (13)0.0068 (12)
C130.0451 (14)0.0457 (14)0.0427 (13)0.0033 (12)0.0038 (12)0.0026 (11)
C140.0372 (12)0.0394 (12)0.0435 (13)0.0027 (11)0.0003 (11)0.0034 (10)
C150.0427 (13)0.0425 (13)0.0573 (15)0.0068 (12)0.0031 (13)0.0073 (11)
C160.0492 (15)0.0398 (13)0.0456 (13)0.0055 (12)0.0043 (12)0.0015 (10)
C170.0551 (16)0.0493 (14)0.0440 (14)0.0038 (14)0.0023 (14)0.0056 (11)
C180.0753 (19)0.0627 (17)0.0464 (15)0.0062 (16)0.0069 (15)0.0020 (12)
C190.0553 (16)0.0488 (14)0.0603 (16)0.0011 (14)0.0109 (14)0.0103 (12)
C200.0674 (18)0.0435 (15)0.0452 (13)0.0021 (14)0.0037 (14)0.0066 (11)
C210.0682 (19)0.0408 (14)0.0529 (16)0.0106 (14)0.0089 (15)0.0002 (12)
C220.099 (2)0.0444 (15)0.0638 (17)0.0037 (17)0.0031 (19)0.0007 (13)
C230.135 (4)0.0431 (16)0.077 (2)0.016 (2)0.016 (3)0.0110 (15)
C250.077 (2)0.076 (2)0.134 (3)0.027 (2)0.000 (3)0.034 (2)
C260.064 (2)0.0507 (17)0.108 (3)0.0149 (16)0.005 (2)0.0170 (17)
C27A0.104 (5)0.041 (3)0.085 (4)0.014 (3)0.018 (4)0.005 (3)
C28A0.132 (7)0.080 (7)0.066 (5)0.039 (6)0.015 (5)0.007 (5)
C29A0.085 (4)0.062 (3)0.092 (4)0.023 (4)0.023 (4)0.005 (3)
C240.092 (3)0.069 (2)0.104 (3)0.034 (2)0.012 (3)0.029 (2)
C27B0.092 (5)0.030 (4)0.088 (5)0.003 (4)0.001 (4)0.005 (4)
C28B0.106 (8)0.045 (6)0.079 (8)0.020 (6)0.026 (7)0.017 (6)
C29B0.082 (6)0.062 (5)0.102 (6)0.017 (5)0.022 (5)0.007 (5)
Geometric parameters (Å, º) top
O3—C31.233 (3)C16—C201.339 (3)
O17—C171.223 (3)C16—C171.495 (4)
C1—C21.520 (4)C18—H18A0.9800
C1—C101.542 (4)C18—H18B0.9800
C1—H1A0.9900C18—H18C0.9800
C1—H1B0.9900C19—H19A0.9800
C2—C31.485 (5)C19—H19B0.9800
C2—H2A0.9900C19—H19C0.9800
C2—H2B0.9900C20—C211.457 (4)
C3—C41.478 (4)C20—H200.9500
C4—C51.338 (4)C21—C261.376 (5)
C4—H40.9500C21—C221.400 (4)
C5—C61.499 (4)C22—C231.394 (5)
C5—C101.517 (4)C22—H220.9500
C6—C71.522 (3)C23—C241.372 (6)
C6—H6A0.9900C23—H230.9500
C6—H6B0.9900C25—C241.374 (5)
C7—C81.524 (3)C25—C261.390 (4)
C7—H7A0.9900C25—H250.9500
C7—H7B0.9900C26—H260.9500
C8—C141.521 (3)C27A—C28A1.538 (5)
C8—C91.538 (3)C27A—C29A1.538 (4)
C8—H81.0000C27A—C241.549 (4)
C9—C111.542 (3)C27A—H27A1.0000
C9—C101.570 (3)C28A—H28A0.9800
C9—H91.0000C28A—H28B0.9800
C10—C191.542 (3)C28A—H28C0.9800
C11—C121.535 (4)C29A—H29A0.9800
C11—H11A0.9900C29A—H29B0.9800
C11—H11B0.9900C29A—H29C0.9800
C12—C131.516 (3)C24—C27B1.538 (4)
C12—H12A0.9900C27B—C29B1.541 (5)
C12—H12B0.9900C27B—C28B1.541 (5)
C13—C171.515 (4)C27B—H27B1.0000
C13—C181.540 (4)C28B—H28D0.9800
C13—C141.545 (3)C28B—H28E0.9800
C14—C151.541 (3)C28B—H28F0.9800
C14—H141.0000C29B—H29D0.9800
C15—C161.512 (4)C29B—H29E0.9800
C15—H15A0.9900C29B—H29F0.9800
C15—H15B0.9900
C2—C1—C10113.1 (2)C15—C14—H14105.7
C2—C1—H1A109.0C13—C14—H14105.7
C10—C1—H1A109.0C16—C15—C14101.82 (19)
C2—C1—H1B109.0C16—C15—H15A111.4
C10—C1—H1B109.0C14—C15—H15A111.4
H1A—C1—H1B107.8C16—C15—H15B111.4
C3—C2—C1111.1 (2)C14—C15—H15B111.4
C3—C2—H2A109.4H15A—C15—H15B109.3
C1—C2—H2A109.4C20—C16—C17120.6 (3)
C3—C2—H2B109.4C20—C16—C15131.2 (2)
C1—C2—H2B109.4C17—C16—C15108.11 (19)
H2A—C2—H2B108.0O17—C17—C16126.4 (2)
O3—C3—C4120.1 (4)O17—C17—C13126.0 (2)
O3—C3—C2123.4 (3)C16—C17—C13107.6 (2)
C4—C3—C2116.5 (3)C13—C18—H18A109.5
C5—C4—C3123.6 (3)C13—C18—H18B109.5
C5—C4—H4118.2H18A—C18—H18B109.5
C3—C4—H4118.2C13—C18—H18C109.5
C4—C5—C6120.6 (3)H18A—C18—H18C109.5
C4—C5—C10122.3 (3)H18B—C18—H18C109.5
C6—C5—C10117.0 (2)C10—C19—H19A109.5
C5—C6—C7112.3 (2)C10—C19—H19B109.5
C5—C6—H6A109.1H19A—C19—H19B109.5
C7—C6—H6A109.1C10—C19—H19C109.5
C5—C6—H6B109.1H19A—C19—H19C109.5
C7—C6—H6B109.1H19B—C19—H19C109.5
H6A—C6—H6B107.9C16—C20—C21130.5 (3)
C6—C7—C8110.1 (2)C16—C20—H20114.8
C6—C7—H7A109.6C21—C20—H20114.8
C8—C7—H7A109.6C26—C21—C22117.3 (3)
C6—C7—H7B109.6C26—C21—C20124.9 (3)
C8—C7—H7B109.6C22—C21—C20117.8 (3)
H7A—C7—H7B108.2C23—C22—C21120.2 (4)
C14—C8—C7111.48 (18)C23—C22—H22119.9
C14—C8—C9107.94 (19)C21—C22—H22119.9
C7—C8—C9110.65 (19)C24—C23—C22122.3 (3)
C14—C8—H8108.9C24—C23—H23118.9
C7—C8—H8108.9C22—C23—H23118.9
C9—C8—H8108.9C24—C25—C26122.2 (4)
C8—C9—C11111.59 (19)C24—C25—H25118.9
C8—C9—C10113.9 (2)C26—C25—H25118.9
C11—C9—C10112.57 (19)C21—C26—C25121.0 (3)
C8—C9—H9106.0C21—C26—H26119.5
C11—C9—H9106.0C25—C26—H26119.5
C10—C9—H9106.0C28A—C27A—C29A110.8 (7)
C5—C10—C1109.8 (2)C28A—C27A—C24106.6 (5)
C5—C10—C19107.9 (2)C29A—C27A—C24107.6 (4)
C1—C10—C19110.1 (2)C28A—C27A—H27A110.6
C5—C10—C9109.60 (19)C29A—C27A—H27A110.6
C1—C10—C9108.2 (2)C24—C27A—H27A110.6
C19—C10—C9111.3 (2)C23—C24—C25116.8 (3)
C12—C11—C9113.00 (19)C23—C24—C27B104.2 (4)
C12—C11—H11A109.0C25—C24—C27B138.1 (4)
C9—C11—H11A109.0C23—C24—C27A129.9 (4)
C12—C11—H11B109.0C25—C24—C27A113.0 (4)
C9—C11—H11B109.0C24—C27B—C29B104.4 (5)
H11A—C11—H11B107.8C24—C27B—C28B106.8 (5)
C13—C12—C11110.5 (2)C29B—C27B—C28B109.5 (7)
C13—C12—H12A109.6C24—C27B—H27B111.9
C11—C12—H12A109.5C29B—C27B—H27B111.9
C13—C12—H12B109.6C28B—C27B—H27B111.9
C11—C12—H12B109.6C27B—C28B—H28D109.5
H12A—C12—H12B108.1C27B—C28B—H28E109.5
C17—C13—C12116.4 (2)H28D—C28B—H28E109.5
C17—C13—C18106.4 (2)C27B—C28B—H28F109.5
C12—C13—C18112.3 (2)H28D—C28B—H28F109.5
C17—C13—C1499.69 (19)H28E—C28B—H28F109.5
C12—C13—C14108.43 (19)C27B—C29B—H29D109.5
C18—C13—C14113.1 (2)C27B—C29B—H29E109.5
C8—C14—C15121.28 (19)H29D—C29B—H29E109.5
C8—C14—C13113.27 (19)C27B—C29B—H29F109.5
C15—C14—C13104.15 (19)H29D—C29B—H29F109.5
C8—C14—H14105.7H29E—C29B—H29F109.5
C10—C1—C2—C356.1 (3)C18—C13—C14—C864.0 (3)
C1—C2—C3—O3147.8 (3)C17—C13—C14—C1542.8 (2)
C1—C2—C3—C433.7 (4)C12—C13—C14—C15165.03 (19)
O3—C3—C4—C5176.0 (3)C18—C13—C14—C1569.8 (2)
C2—C3—C4—C55.4 (4)C8—C14—C15—C16166.9 (2)
C3—C4—C5—C6174.4 (2)C13—C14—C15—C1637.9 (2)
C3—C4—C5—C101.7 (4)C14—C15—C16—C20158.0 (3)
C4—C5—C6—C7132.2 (3)C14—C15—C16—C1717.8 (2)
C10—C5—C6—C751.5 (3)C20—C16—C17—O175.9 (4)
C5—C6—C7—C855.8 (3)C15—C16—C17—O17170.5 (2)
C6—C7—C8—C14178.0 (2)C20—C16—C17—C13174.6 (2)
C6—C7—C8—C957.8 (3)C15—C16—C17—C139.0 (3)
C14—C8—C9—C1154.0 (2)C12—C13—C17—O1731.6 (4)
C7—C8—C9—C11176.3 (2)C18—C13—C17—O1794.4 (3)
C14—C8—C9—C10177.17 (19)C14—C13—C17—O17147.9 (3)
C7—C8—C9—C1054.9 (3)C12—C13—C17—C16147.9 (2)
C4—C5—C10—C119.6 (3)C18—C13—C17—C1686.1 (2)
C6—C5—C10—C1164.2 (2)C14—C13—C17—C1631.6 (2)
C4—C5—C10—C19100.4 (3)C17—C16—C20—C21176.6 (3)
C6—C5—C10—C1975.8 (3)C15—C16—C20—C211.2 (5)
C4—C5—C10—C9138.3 (3)C16—C20—C21—C2614.2 (5)
C6—C5—C10—C945.5 (3)C16—C20—C21—C22165.2 (3)
C2—C1—C10—C548.2 (3)C26—C21—C22—C233.5 (4)
C2—C1—C10—C1970.4 (3)C20—C21—C22—C23176.0 (3)
C2—C1—C10—C9167.8 (2)C21—C22—C23—C240.1 (5)
C8—C9—C10—C546.9 (3)C22—C21—C26—C253.6 (5)
C11—C9—C10—C5175.25 (19)C20—C21—C26—C25175.8 (3)
C8—C9—C10—C1166.6 (2)C24—C25—C26—C210.4 (6)
C11—C9—C10—C165.1 (3)C22—C23—C24—C253.1 (5)
C8—C9—C10—C1972.3 (3)C22—C23—C24—C27B174.4 (4)
C11—C9—C10—C1956.0 (3)C22—C23—C24—C27A169.7 (4)
C8—C9—C11—C1253.7 (3)C26—C25—C24—C233.0 (6)
C10—C9—C11—C12176.8 (2)C26—C25—C24—C27B170.2 (6)
C9—C11—C12—C1354.7 (3)C26—C25—C24—C27A171.1 (4)
C11—C12—C13—C17167.6 (2)C28A—C27A—C24—C2346.8 (10)
C11—C12—C13—C1869.4 (3)C29A—C27A—C24—C2372.1 (6)
C11—C12—C13—C1456.2 (3)C28A—C27A—C24—C25126.3 (8)
C7—C8—C14—C1554.0 (3)C29A—C27A—C24—C25114.8 (5)
C9—C8—C14—C15175.7 (2)C23—C24—C27B—C29B151.1 (5)
C7—C8—C14—C13178.9 (2)C25—C24—C27B—C29B17.1 (9)
C9—C8—C14—C1359.3 (2)C23—C24—C27B—C28B92.9 (9)
C17—C13—C14—C8176.55 (19)C25—C24—C27B—C28B98.9 (11)
C12—C13—C14—C861.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O17i0.992.573.321 (4)132
C28A—H28A···O3ii0.982.573.32 (2)134
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC29H36O2
Mr416.58
Crystal system, space groupOrthorhombic, P212121
Temperature (K)160
a, b, c (Å)6.1318 (2), 17.3938 (5), 22.3210 (7)
V3)2380.65 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.25 × 0.20 × 0.18
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
22900, 2437, 2000
Rint0.055
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.116, 1.04
No. of reflections2436
No. of parameters315
No. of restraints87
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.16

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 (Farrugia, 1997), SHELXL97 and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O17i0.992.573.321 (4)132
C28A—H28A···O3ii0.982.573.32 (2)134
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x, y1, z.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds