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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 Feb 25;65(Pt 3):o587. doi: 10.1107/S1600536809005741

N-tert-Butyl-5α-androstane-17β-carboxamide

Xin Yan a, Shiqing Xu a, Jingmei Wang b, Ying Chen a, Peng Xia a,*
PMCID: PMC2968652  PMID: 21582242

Abstract

The title compound, C24H41NO, is a new derivative of the anti-HIV steroid 17β-(N-tert-butyl­amino­carbon­yl)androst-4-en-3-one. There are four rings in the structure and these are trans-fused. The three six-membered rings exhibit chair conformations, while the five-membered ring adopts an envelope conformation.

Related literature

For the anti-HIV activity of 17β-(N-tert-butyl­amino­carbon­yl)-androst-4-en-3-one, see: Xia et al. (1999 ▶). For discussion of absolute configuration, see: Marker et al. (1940 ▶); Fieser & Fieser (1959 ▶); Throop & Tokes (1967 ▶); House (1972 ▶); Castro-Méndez et al. (2002 ▶).graphic file with name e-65-0o587-scheme1.jpg

Experimental

Crystal data

  • C24H41NO

  • M r = 359.58

  • Orthorhombic, Inline graphic

  • a = 6.373 (2) Å

  • b = 12.802 (4) Å

  • c = 26.775 (9) Å

  • V = 2184.3 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 294 K

  • 0.15 × 0.08 × 0.06 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.990, T max = 0.996

  • 10583 measured reflections

  • 2757 independent reflections

  • 1433 reflections with I > 2σ(I)

  • R int = 0.063

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037

  • wR(F 2) = 0.068

  • S = 0.75

  • 2757 reflections

  • 240 parameters

  • H-atom parameters constrained

  • Δρmax = 0.10 e Å−3

  • Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005741/tk2372sup1.cif

e-65-0o587-sup1.cif (24.4KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005741/tk2372Isup2.hkl

e-65-0o587-Isup2.hkl (135.4KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge the Center of Analysis and Measurement, Fudan University, for providing research facilities.

supplementary crystallographic information

Comment

17β-(N-tert-Butylcarboxamide)-androst-4-ene-3-one was reported to exhibit potent anti-HIV activity in acutely infected H9 lymphocytes with EC50 and therapeutic index values of 0.8 and 300 µM, respectively (Xia et al., 1999). During our work of structural modification, which is motivated by the search for more potent anti-HIV agents, we found that 17β-(N-tert-butylcarboxamide)-5α-androstane (I) could be obtained through Pd/C catalytic hydrogenation of 17β-(N-tert-butylcarboxamide)-androst-4-ene-3-ol in excellent yield (90%); full structural details of (I) are reported herein.

The molecular structure of (I), Fig.1, shows the A/B, B/C and C/D ring junctions to be all trans. The cyclohexane rings adopt chair conformations, and the cyclopentane ring adopts an envelope conformation. Based on the known configurations of the C10, C13-methyl groups, see Experimental, 5-H is assigned an α-configuration. The 17-N-tert-butylcarboxamide group is in a β-configuration. The stereogenic sites of (I) exhibit the following chirality: C5 = R, C8 = R, C9 = S, C10 = S, C13 = S, C14 = S and C17 = S.

Experimental

Compound (I) was prepared from the corresponding 4-ene-3-ol by catalytic hydrogenation with 5% palladium-on-charcoal in EtOH for 1 day. After filtration and removal of the solvent, the residue was crystallized from acetone to give colourless crystals.

The starting material, 17β-(N-tert-butylcarboxamide)-androst-4-ene-3-ol, was obtained from the reduction of 17β-(N-tert-butylcarboxamide)-androst-4-ene-3-one with NaBH4. It is an intermediate in the synthesis of Finasteride and derived initially from diosgenin, for which the absolute configurations of all chiral centers of the steroid skeleton have been determined (Fieser & Fieser, 1959; Marker et al., 1940). Recently, the absolute configurations of the chiral centres were confirmed by the X-ray crystal structure determination of a 3-Br substituted steroid substrate synthesized from diosgenin (Castro-Méndez et al., 2002). The hydrogenation of 4-en-3-one moiety did not cause inversion of the configurations at C8, C9, C10, C13 and C14 (Throop & Tokes, 1967; House, 1972). Thus, by comparing the orientation of 5-H to that of methyl groups at C10 and C13, the absolute configuration of (I) could be determined.

Refinement

All H atoms were placed in the idealized positions with N—H = 0.86 Å, methine C—H = 0.98 Å, methylene C—H = 0.97 Å and methyl C—H = 0.96 Å, and treated as riding with Uiso(H) = 1.2 Ueq(N-H, CH2 and CH) and 1.5Ueq(CH3). In the absence of significant anomalous scattering effects, 1971 Friedel pairs were averaged in the final refinement.

Figures

Fig. 1.

Fig. 1.

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The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C24H41NO Dx = 1.093 Mg m−3
Mr = 359.58 Melting point: 451.5 K
Orthorhombic, P212121 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab Cell parameters from 962 reflections
a = 6.373 (2) Å θ = 2.8–19.0°
b = 12.802 (4) Å µ = 0.07 mm−1
c = 26.775 (9) Å T = 294 K
V = 2184.3 (12) Å3 Parallelepiped, colourless
Z = 4 0.15 × 0.08 × 0.06 mm
F(000) = 800
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Data collection

Bruker SMART CCD area-detector diffractometer 2757 independent reflections
Radiation source: sealed tube 1433 reflections with I > 2σ(I)
graphite Rint = 0.063
φ and ω scans θmax = 27.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −8→8
Tmin = 0.990, Tmax = 0.996 k = −16→16
10583 measured reflections l = −34→22
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068 H-atom parameters constrained
S = 0.75 w = 1/[σ2(Fo2) + (0.0299P)2] where P = (Fo2 + 2Fc2)/3
2757 reflections (Δ/σ)max < 0.001
240 parameters Δρmax = 0.10 e Å−3
0 restraints Δρmin = −0.12 e Å−3
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
N1 0.8035 (3) 0.65842 (13) 0.56653 (6) 0.0540 (5)
H1 0.9247 0.6820 0.5751 0.065*
O1 0.4554 (3) 0.67334 (13) 0.58044 (5) 0.0666 (5)
C1 1.1936 (4) 0.62769 (17) 0.84810 (7) 0.0534 (6)
H1A 1.2184 0.5667 0.8274 0.064*
H1B 1.2916 0.6815 0.8377 0.064*
C2 1.2381 (4) 0.59935 (18) 0.90230 (7) 0.0614 (7)
H2A 1.1548 0.5388 0.9114 0.074*
H2B 1.3849 0.5806 0.9057 0.074*
C3 1.1892 (4) 0.6872 (2) 0.93761 (8) 0.0682 (7)
H3A 1.2928 0.7420 0.9334 0.082*
H3B 1.1993 0.6618 0.9717 0.082*
C4 0.9727 (4) 0.73240 (19) 0.92929 (7) 0.0635 (7)
H4A 0.9568 0.7949 0.9494 0.076*
H4B 0.8681 0.6822 0.9402 0.076*
C5 0.9344 (4) 0.75945 (17) 0.87460 (7) 0.0522 (6)
H5 1.0430 0.8106 0.8660 0.063*
C6 0.7298 (4) 0.81485 (17) 0.86688 (7) 0.0610 (7)
H6A 0.7239 0.8752 0.8887 0.073*
H6B 0.6157 0.7685 0.8760 0.073*
C7 0.7000 (4) 0.85044 (16) 0.81299 (7) 0.0614 (7)
H7A 0.5601 0.8792 0.8091 0.074*
H7B 0.8002 0.9053 0.8055 0.074*
C8 0.7295 (3) 0.76086 (15) 0.77615 (7) 0.0426 (5)
H8 0.6196 0.7091 0.7826 0.051*
C9 0.9436 (3) 0.70738 (15) 0.78447 (6) 0.0397 (5)
H9 1.0496 0.7621 0.7802 0.048*
C10 0.9693 (3) 0.66681 (15) 0.83881 (7) 0.0400 (5)
C11 0.9900 (4) 0.62511 (16) 0.74440 (7) 0.0508 (6)
H11A 0.9022 0.5646 0.7505 0.061*
H11B 1.1350 0.6031 0.7477 0.061*
C12 0.9537 (3) 0.66238 (17) 0.69070 (7) 0.0499 (6)
H12A 1.0565 0.7154 0.6823 0.060*
H12B 0.9722 0.6042 0.6679 0.060*
C13 0.7344 (3) 0.70711 (14) 0.68449 (7) 0.0382 (5)
C14 0.7092 (3) 0.79588 (15) 0.72231 (7) 0.0436 (5)
H14 0.8250 0.8446 0.7162 0.052*
C15 0.5092 (4) 0.85175 (17) 0.70618 (7) 0.0567 (6)
H15A 0.5117 0.9245 0.7163 0.068*
H15B 0.3863 0.8185 0.7205 0.068*
C16 0.5093 (4) 0.84178 (16) 0.64878 (7) 0.0599 (7)
H16A 0.5323 0.9095 0.6334 0.072*
H16B 0.3760 0.8145 0.6372 0.072*
C17 0.6889 (4) 0.76619 (14) 0.63516 (6) 0.0442 (6)
H17 0.8130 0.8077 0.6266 0.053*
C18 0.5691 (4) 0.62057 (15) 0.69106 (7) 0.0539 (6)
H18A 0.5990 0.5642 0.6685 0.081*
H18B 0.4323 0.6483 0.6840 0.081*
H18C 0.5730 0.5952 0.7248 0.081*
C19 0.8159 (4) 0.57727 (15) 0.84878 (8) 0.0584 (7)
H19A 0.8546 0.5178 0.8290 0.088*
H19B 0.6764 0.5989 0.8401 0.088*
H19C 0.8204 0.5589 0.8835 0.088*
C20 0.6366 (4) 0.69668 (16) 0.59120 (8) 0.0487 (6)
C21 0.7988 (4) 0.58025 (17) 0.52642 (8) 0.0598 (7)
C22 0.6959 (5) 0.48089 (17) 0.54580 (9) 0.0912 (9)
H22A 0.7737 0.4550 0.5739 0.137*
H22B 0.6947 0.4292 0.5198 0.137*
H22C 0.5545 0.4959 0.5559 0.137*
C23 1.0254 (5) 0.5606 (2) 0.51203 (10) 0.1023 (10)
H23A 1.0853 0.6236 0.4988 0.153*
H23B 1.0314 0.5066 0.4872 0.153*
H23C 1.1031 0.5392 0.5410 0.153*
C24 0.6785 (5) 0.6221 (2) 0.48153 (8) 0.0816 (8)
H24A 0.5353 0.6348 0.4908 0.122*
H24B 0.6828 0.5717 0.4550 0.122*
H24C 0.7415 0.6861 0.4705 0.122*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
N1 0.0549 (14) 0.0628 (12) 0.0443 (11) −0.0034 (11) 0.0022 (10) −0.0105 (10)
O1 0.0572 (12) 0.0831 (11) 0.0595 (10) −0.0006 (11) −0.0099 (9) −0.0130 (9)
C1 0.0520 (16) 0.0652 (14) 0.0430 (13) 0.0011 (13) −0.0016 (12) −0.0034 (11)
C2 0.0565 (18) 0.0790 (15) 0.0486 (14) 0.0058 (14) −0.0050 (12) 0.0054 (13)
C3 0.075 (2) 0.0871 (18) 0.0425 (14) 0.0031 (17) −0.0089 (14) 0.0036 (13)
C4 0.072 (2) 0.0781 (17) 0.0407 (14) 0.0077 (16) 0.0017 (13) −0.0055 (12)
C5 0.0539 (17) 0.0644 (15) 0.0382 (13) 0.0022 (14) 0.0015 (12) −0.0031 (11)
C6 0.069 (2) 0.0696 (15) 0.0443 (14) 0.0139 (14) −0.0002 (12) −0.0153 (12)
C7 0.0739 (18) 0.0619 (14) 0.0483 (14) 0.0217 (14) 0.0024 (13) −0.0083 (12)
C8 0.0440 (15) 0.0451 (12) 0.0386 (12) 0.0060 (11) 0.0060 (10) −0.0030 (10)
C9 0.0386 (13) 0.0454 (12) 0.0351 (12) −0.0033 (11) 0.0036 (10) −0.0027 (10)
C10 0.0367 (14) 0.0471 (12) 0.0363 (12) −0.0011 (11) 0.0051 (10) 0.0010 (10)
C11 0.0466 (15) 0.0642 (14) 0.0415 (12) 0.0151 (12) −0.0001 (11) −0.0012 (11)
C12 0.0482 (15) 0.0620 (14) 0.0395 (12) 0.0051 (13) 0.0042 (11) −0.0075 (11)
C13 0.0392 (14) 0.0419 (11) 0.0336 (11) 0.0017 (11) 0.0008 (10) −0.0009 (10)
C14 0.0486 (15) 0.0413 (11) 0.0409 (12) 0.0021 (12) 0.0023 (11) 0.0032 (10)
C15 0.0699 (19) 0.0552 (14) 0.0451 (13) 0.0215 (14) −0.0044 (12) −0.0012 (11)
C16 0.0740 (19) 0.0529 (13) 0.0527 (14) 0.0134 (14) −0.0027 (13) 0.0028 (12)
C17 0.0508 (15) 0.0464 (12) 0.0355 (12) −0.0004 (12) −0.0007 (11) 0.0017 (10)
C18 0.0607 (16) 0.0527 (13) 0.0485 (14) −0.0046 (13) 0.0004 (12) 0.0035 (11)
C19 0.0584 (18) 0.0646 (15) 0.0522 (14) −0.0089 (14) −0.0024 (13) 0.0098 (12)
C20 0.0608 (18) 0.0484 (13) 0.0370 (13) 0.0006 (14) 0.0000 (13) 0.0067 (11)
C21 0.073 (2) 0.0573 (14) 0.0492 (14) 0.0029 (14) 0.0018 (13) −0.0104 (13)
C22 0.135 (3) 0.0530 (15) 0.0855 (19) −0.0078 (19) 0.0009 (19) −0.0047 (14)
C23 0.085 (2) 0.124 (2) 0.098 (2) 0.017 (2) 0.016 (2) −0.0481 (19)
C24 0.113 (2) 0.0870 (17) 0.0447 (14) −0.0078 (18) −0.0044 (16) −0.0127 (14)
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Geometric parameters (Å, °)

N1—C20 1.345 (3) C11—H11B 0.9700
N1—C21 1.468 (3) C12—C13 1.519 (3)
N1—H1 0.8600 C12—H12A 0.9700
O1—C20 1.227 (3) C12—H12B 0.9700
C1—C2 1.522 (3) C13—C14 1.531 (3)
C1—C10 1.535 (3) C13—C18 1.539 (3)
C1—H1A 0.9700 C13—C17 1.549 (3)
C1—H1B 0.9700 C14—C15 1.524 (3)
C2—C3 1.502 (3) C14—H14 0.9800
C2—H2A 0.9700 C15—C16 1.542 (2)
C2—H2B 0.9700 C15—H15A 0.9700
C3—C4 1.513 (3) C15—H15B 0.9700
C3—H3A 0.9700 C16—C17 1.542 (3)
C3—H3B 0.9700 C16—H16A 0.9700
C4—C5 1.524 (3) C16—H16B 0.9700
C4—H4A 0.9700 C17—C20 1.513 (3)
C4—H4B 0.9700 C17—H17 0.9800
C5—C6 1.498 (3) C18—H18A 0.9599
C5—C10 1.541 (3) C18—H18B 0.9599
C5—H5 0.9800 C18—H18C 0.9599
C6—C7 1.525 (2) C19—H19A 0.9599
C6—H6A 0.9700 C19—H19B 0.9599
C6—H6B 0.9700 C19—H19C 0.9599
C7—C8 1.524 (2) C21—C23 1.516 (4)
C7—H7A 0.9700 C21—C24 1.523 (3)
C7—H7B 0.9700 C21—C22 1.522 (3)
C8—C14 1.515 (2) C22—H22A 0.9599
C8—C9 1.542 (3) C22—H22B 0.9599
C8—H8 0.9800 C22—H22C 0.9599
C9—C11 1.532 (2) C23—H23A 0.9599
C9—C10 1.554 (2) C23—H23B 0.9599
C9—H9 0.9800 C23—H23C 0.9599
C10—C19 1.530 (3) C24—H24A 0.9599
C11—C12 1.532 (3) C24—H24B 0.9599
C11—H11A 0.9700 C24—H24C 0.9599
C20—N1—C21 126.2 (2) C13—C12—H12B 109.4
C20—N1—H1 116.9 C11—C12—H12B 109.4
C21—N1—H1 116.9 H12A—C12—H12B 108.0
C2—C1—C10 113.91 (17) C12—C13—C14 107.69 (17)
C2—C1—H1A 108.8 C12—C13—C18 110.23 (17)
C10—C1—H1A 108.8 C14—C13—C18 112.79 (16)
C2—C1—H1B 108.8 C12—C13—C17 116.70 (16)
C10—C1—H1B 108.8 C14—C13—C17 100.48 (14)
H1A—C1—H1B 107.7 C18—C13—C17 108.70 (17)
C3—C2—C1 112.51 (19) C8—C14—C15 118.68 (17)
C3—C2—H2A 109.1 C8—C14—C13 113.62 (16)
C1—C2—H2A 109.1 C15—C14—C13 104.39 (16)
C3—C2—H2B 109.1 C8—C14—H14 106.5
C1—C2—H2B 109.1 C15—C14—H14 106.5
H2A—C2—H2B 107.8 C13—C14—H14 106.5
C2—C3—C4 112.5 (2) C14—C15—C16 104.07 (17)
C2—C3—H3A 109.1 C14—C15—H15A 110.9
C4—C3—H3A 109.1 C16—C15—H15A 110.9
C2—C3—H3B 109.1 C14—C15—H15B 110.9
C4—C3—H3B 109.1 C16—C15—H15B 110.9
H3A—C3—H3B 107.8 H15A—C15—H15B 109.0
C3—C4—C5 111.98 (19) C15—C16—C17 106.73 (16)
C3—C4—H4A 109.2 C15—C16—H16A 110.4
C5—C4—H4A 109.2 C17—C16—H16A 110.4
C3—C4—H4B 109.2 C15—C16—H16B 110.4
C5—C4—H4B 109.2 C17—C16—H16B 110.4
H4A—C4—H4B 107.9 H16A—C16—H16B 108.6
C6—C5—C4 112.29 (18) C20—C17—C16 112.92 (19)
C6—C5—C10 113.84 (17) C20—C17—C13 114.68 (16)
C4—C5—C10 113.54 (18) C16—C17—C13 104.10 (15)
C6—C5—H5 105.4 C20—C17—H17 108.3
C4—C5—H5 105.4 C16—C17—H17 108.3
C10—C5—H5 105.4 C13—C17—H17 108.3
C5—C6—C7 112.36 (18) C13—C18—H18A 109.5
C5—C6—H6A 109.1 C13—C18—H18B 109.5
C7—C6—H6A 109.1 H18A—C18—H18B 109.5
C5—C6—H6B 109.1 C13—C18—H18C 109.5
C7—C6—H6B 109.1 H18A—C18—H18C 109.5
H6A—C6—H6B 107.9 H18B—C18—H18C 109.5
C8—C7—C6 111.84 (16) C10—C19—H19A 109.5
C8—C7—H7A 109.2 C10—C19—H19B 109.5
C6—C7—H7A 109.2 H19A—C19—H19B 109.5
C8—C7—H7B 109.2 C10—C19—H19C 109.5
C6—C7—H7B 109.2 H19A—C19—H19C 109.5
H7A—C7—H7B 107.9 H19B—C19—H19C 109.5
C14—C8—C7 112.48 (16) O1—C20—N1 122.7 (2)
C14—C8—C9 110.13 (16) O1—C20—C17 122.2 (2)
C7—C8—C9 110.47 (17) N1—C20—C17 115.0 (2)
C14—C8—H8 107.9 N1—C21—C23 106.2 (2)
C7—C8—H8 107.9 N1—C21—C24 110.37 (18)
C9—C8—H8 107.9 C23—C21—C24 109.7 (2)
C11—C9—C8 112.02 (16) N1—C21—C22 109.20 (18)
C11—C9—C10 113.93 (16) C23—C21—C22 111.0 (2)
C8—C9—C10 112.15 (15) C24—C21—C22 110.2 (2)
C11—C9—H9 106.0 C21—C22—H22A 109.5
C8—C9—H9 106.0 C21—C22—H22B 109.5
C10—C9—H9 106.0 H22A—C22—H22B 109.5
C19—C10—C1 108.81 (17) C21—C22—H22C 109.5
C19—C10—C5 112.08 (16) H22A—C22—H22C 109.5
C1—C10—C5 106.56 (16) H22B—C22—H22C 109.5
C19—C10—C9 110.26 (16) C21—C23—H23A 109.5
C1—C10—C9 111.04 (15) C21—C23—H23B 109.5
C5—C10—C9 108.05 (15) H23A—C23—H23B 109.5
C9—C11—C12 114.43 (17) C21—C23—H23C 109.5
C9—C11—H11A 108.7 H23A—C23—H23C 109.5
C12—C11—H11A 108.7 H23B—C23—H23C 109.5
C9—C11—H11B 108.7 C21—C24—H24A 109.5
C12—C11—H11B 108.7 C21—C24—H24B 109.5
H11A—C11—H11B 107.6 H24A—C24—H24B 109.5
C13—C12—C11 111.04 (16) C21—C24—H24C 109.5
C13—C12—H12A 109.4 H24A—C24—H24C 109.5
C11—C12—H12A 109.4 H24B—C24—H24C 109.5
C10—C1—C2—C3 −54.5 (3) C11—C12—C13—C18 −66.3 (2)
C1—C2—C3—C4 50.1 (3) C11—C12—C13—C17 169.09 (17)
C2—C3—C4—C5 −50.5 (3) C7—C8—C14—C15 −55.7 (3)
C3—C4—C5—C6 −173.8 (2) C9—C8—C14—C15 −179.44 (17)
C3—C4—C5—C10 55.3 (3) C7—C8—C14—C13 −179.00 (18)
C4—C5—C6—C7 175.0 (2) C9—C8—C14—C13 57.3 (2)
C10—C5—C6—C7 −54.3 (2) C12—C13—C14—C8 −61.5 (2)
C5—C6—C7—C8 53.1 (3) C18—C13—C14—C8 60.3 (2)
C6—C7—C8—C14 −177.64 (18) C17—C13—C14—C8 175.87 (17)
C6—C7—C8—C9 −54.1 (2) C12—C13—C14—C15 167.69 (17)
C14—C8—C9—C11 −48.6 (2) C18—C13—C14—C15 −70.46 (19)
C7—C8—C9—C11 −173.49 (17) C17—C13—C14—C15 45.1 (2)
C14—C8—C9—C10 −178.19 (16) C8—C14—C15—C16 −161.48 (18)
C7—C8—C9—C10 56.9 (2) C13—C14—C15—C16 −33.8 (2)
C2—C1—C10—C19 −65.7 (2) C14—C15—C16—C17 8.8 (2)
C2—C1—C10—C5 55.4 (2) C15—C16—C17—C20 143.81 (18)
C2—C1—C10—C9 172.80 (17) C15—C16—C17—C13 18.8 (2)
C6—C5—C10—C19 −67.1 (2) C12—C13—C17—C20 81.4 (2)
C4—C5—C10—C19 63.0 (2) C14—C13—C17—C20 −162.6 (2)
C6—C5—C10—C1 173.94 (18) C18—C13—C17—C20 −44.0 (2)
C4—C5—C10—C1 −55.9 (2) C12—C13—C17—C16 −154.74 (18)
C6—C5—C10—C9 54.5 (2) C14—C13—C17—C16 −38.70 (19)
C4—C5—C10—C9 −175.31 (19) C18—C13—C17—C16 79.89 (18)
C11—C9—C10—C19 −61.5 (2) C21—N1—C20—O1 −4.2 (3)
C8—C9—C10—C19 67.1 (2) C21—N1—C20—C17 172.60 (17)
C11—C9—C10—C1 59.2 (2) C16—C17—C20—O1 −26.4 (3)
C8—C9—C10—C1 −172.21 (16) C13—C17—C20—O1 92.6 (3)
C11—C9—C10—C5 175.74 (18) C16—C17—C20—N1 156.77 (17)
C8—C9—C10—C5 −55.7 (2) C13—C17—C20—N1 −84.2 (2)
C8—C9—C11—C12 48.2 (2) C20—N1—C21—C23 −178.2 (2)
C10—C9—C11—C12 176.84 (18) C20—N1—C21—C24 62.9 (3)
C9—C11—C12—C13 −53.2 (2) C20—N1—C21—C22 −58.5 (3)
C11—C12—C13—C14 57.1 (2)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2372).

References

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  2. Castro-Méndez, A., Sandoval-Ramírez, J. & Bernès, S. (2002). Acta Cryst. E58, o606–o608.
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  5. Marker, R. E., Tsukamoto, T. & Turner, D. L. (1940). J. Am. Chem. Soc.62, 2525–2532.
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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005741/tk2372sup1.cif

e-65-0o587-sup1.cif (24.4KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005741/tk2372Isup2.hkl

e-65-0o587-Isup2.hkl (135.4KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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