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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o73.
Published online 2008 December 10. doi:  10.1107/S1600536808040877
PMCID: PMC2967983

(E)-3-Hydr­oxy-13-methyl-16-[4-(methyl­sulfan­yl)benzyl­idene]-7,8,9,11,12,13,15,16-octa­hydro-6H-cyclo­penta­[a]phen­an­­­­thren-17(14H)-one

Abstract

In the title compound, C26H28O2S, the dihedral angles between the mean plane of the five membered ring and the 4-(methyl­sulfan­yl)benzyl­idine ring in the two crystallographically independent mol­ecules are 34.05 (10) and 40.53 (15)°. The packing is stabilized by inter­molecular O—H(...)O and C—H(...)O inter­actions.

Related literature

For the biological activity of testosterone derivatives, see: Alvarez-Ginarte et al. (2005 [triangle]). For puckering parameters, see: Cremer & Pople (1975 [triangle]). For related structures, see: Suitchmezian et al. (2007 [triangle]); Ye (2007 [triangle]).

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Object name is e-65-00o73-scheme1.jpg

Experimental

Crystal data

  • C26H28O2S
  • M r = 404.54
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-00o73-efi1.jpg
  • a = 11.9654 (3) Å
  • b = 13.0262 (4) Å
  • c = 27.9441 (8) Å
  • V = 4355.5 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.17 mm−1
  • T = 293 (2) K
  • 0.25 × 0.20 × 0.15 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.959, T max = 0.975
  • 21727 measured reflections
  • 6847 independent reflections
  • 4775 reflections with I > 2σ(I)
  • R int = 0.040
  • θmax = 24.1°

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.142
  • S = 1.06
  • 6847 reflections
  • 529 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.30 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2995 Friedel pairs
  • Flack parameter: −0.06 (11)

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040877/bt2822sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040877/bt2822Isup2.hkl

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

Acknowledgments

BG thanks AMET University management, India, for their kind support.

supplementary crystallographic information

Comment

Testosterone derivatives exhibit a high level of biological activity and have been widely used as hormone treatments (Alvarez-Ginarte et al., 2005).

The five membered rings C13/C14/C16/C17/C18, C39/C40/C42/C43/C44 and 4-(methylsulfanyl)benzylidine rings of the two independent molecules are planar. The C11—C14/C6/C5 and C4—C9 in molecule(I), C37—C40/C32/C31 and C30—C35 in molecule(II) rings have chair conformation (Cremer & Pople, 1975). The dihedral angle between C8/C7/C4/C5 and C11/C12/C14/C6 planes in molecule (I), C33/C34/C30/C31 and C32/C40/C37/C38 planes in molecule (II) are 4.62 (13) and 4.23 (14) °. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing through intermolecular O—H···O and C—H···O interactions.

Experimental

1.0 mol of 4-(methylsulfanyl) benzaldehyde (1.0 g) was dissolved in methanol containing 0.1 g of sodium hydroxide. To this solution 1.0 mol of estrone (0.56 g) was added. The solution was stirred overnight at room temperature. The crude solid was filtered off and then recrystallized in ethanol.

Refinement

H atoms were positioned geometrically and refined using a riding model with O—H = 0.82Å and Uiso(H) = 1.2Ueq(O), C—H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.97Å and Uiso(H) = 1.2Ueq(C) for CH2, C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for CH3.

Figures

Fig. 1.
The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The packing of the title compound, viewed down the b axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C26H28O2SF(000) = 1728
Mr = 404.54Dx = 1.234 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4404 reflections
a = 11.9654 (3) Åθ = 1.5–24.1°
b = 13.0262 (4) ŵ = 0.17 mm1
c = 27.9441 (8) ÅT = 293 K
V = 4355.5 (2) Å3Block, pale yellow
Z = 80.25 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII diffractometer6847 independent reflections
Radiation source: fine-focus sealed tube4775 reflections with I > 2σ(I)
graphiteRint = 0.040
Detector resolution: 0 pixels mm-1θmax = 24.1°, θmin = 1.5°
ω and [var phi] scansh = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −14→14
Tmin = 0.959, Tmax = 0.975l = −23→32
21727 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.142w = 1/[σ2(Fo2) + (0.0773P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
6847 reflectionsΔρmax = 0.38 e Å3
529 parametersΔρmin = −0.29 e Å3
0 restraintsAbsolute structure: Flack (1983), 2995 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.06 (11)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S2−0.2835 (2)0.45026 (18)−0.20650 (6)0.1751 (10)
C52−0.3659 (6)0.3576 (7)−0.2034 (3)0.197 (4)
H52A−0.34430.3135−0.17750.296*
H52B−0.36390.3198−0.23290.296*
H52C−0.44030.3825−0.19800.296*
S10.68074 (10)0.04257 (9)0.06634 (4)0.0772 (4)
C100.0077 (3)−0.1662 (3)0.39329 (13)0.0480 (9)
H10−0.0452−0.17520.36930.058*
C1−0.0260 (2)−0.1691 (3)0.44008 (13)0.0457 (9)
C40.1992 (3)−0.1388 (3)0.41632 (11)0.0419 (8)
O1−0.13439 (17)−0.1845 (2)0.45361 (9)0.0603 (7)
H1−0.1753−0.17950.43020.090*
C110.4053 (2)−0.1657 (3)0.43880 (12)0.0490 (9)
H11A0.3955−0.23960.43960.059*
H11B0.3901−0.13940.47060.059*
C180.5165 (2)−0.1240 (3)0.29171 (11)0.0522 (10)
H18A0.4995−0.18950.27690.063*
H18B0.4896−0.06900.27130.063*
C130.5510 (2)−0.1717 (3)0.37447 (12)0.0421 (8)
C20.0528 (3)−0.1572 (3)0.47588 (12)0.0487 (9)
H20.0315−0.15870.50790.058*
C50.3214 (3)−0.1193 (3)0.40352 (11)0.0422 (8)
H50.3319−0.04470.40520.051*
C30.1637 (3)−0.1429 (3)0.46359 (11)0.0464 (9)
H30.2164−0.13580.48780.056*
C140.4667 (2)−0.1169 (3)0.34152 (11)0.0405 (8)
H140.4708−0.04410.35020.049*
C160.6593 (3)−0.1357 (3)0.35210 (12)0.0499 (9)
C80.1480 (3)−0.1465 (4)0.32801 (11)0.0582 (11)
H8A0.1443−0.21550.31500.070*
H8B0.0928−0.10530.31140.070*
O20.74945 (18)−0.1295 (2)0.37285 (9)0.0679 (8)
C220.7872 (3)0.0394 (3)0.15450 (14)0.0642 (11)
H220.84160.08260.14190.077*
C200.7142 (3)−0.0535 (3)0.22240 (12)0.0486 (9)
C60.3473 (2)−0.1495 (3)0.35240 (11)0.0410 (8)
H60.3428−0.22440.34990.049*
C120.5265 (2)−0.1411 (3)0.42538 (12)0.0523 (10)
H12A0.5397−0.06810.42920.063*
H12B0.5766−0.17740.44680.063*
C190.7213 (3)−0.0814 (3)0.27246 (12)0.0523 (9)
H190.7919−0.07650.28620.063*
C240.6231 (3)−0.0568 (4)0.14629 (14)0.0676 (12)
H240.5646−0.08070.12740.081*
C170.6397 (3)−0.1134 (3)0.30144 (12)0.0474 (9)
C90.1186 (2)−0.1502 (3)0.38065 (12)0.0433 (8)
C70.2624 (3)−0.1029 (3)0.31823 (12)0.0552 (10)
H7A0.2608−0.02890.32220.066*
H7B0.2838−0.11770.28550.066*
C230.7015 (3)0.0076 (3)0.12637 (13)0.0556 (10)
C250.6286 (3)−0.0864 (3)0.19251 (14)0.0644 (11)
H250.5738−0.12980.20460.077*
C150.5518 (3)−0.2884 (3)0.36806 (14)0.0617 (11)
H15A0.5612−0.30470.33480.093*
H15B0.4823−0.31640.37920.093*
H15C0.6123−0.31740.38610.093*
C210.7946 (3)0.0080 (3)0.20193 (14)0.0633 (11)
H210.85530.02910.22030.076*
C260.8118 (4)0.0872 (4)0.04740 (15)0.0892 (15)
H26A0.83570.14210.06790.134*
H26B0.80630.11180.01510.134*
H26C0.86510.03220.04880.134*
C360.4278 (3)0.6531 (3)0.12345 (13)0.0516 (9)
H360.48270.64920.09990.062*
O30.5683 (2)0.6698 (3)0.18447 (10)0.0758 (8)
H3A0.60910.67550.16100.114*
C320.0900 (2)0.6558 (3)0.07867 (11)0.0424 (8)
H320.10210.72850.07140.051*
C40−0.0314 (2)0.6301 (3)0.06840 (12)0.0454 (8)
H40−0.04260.55990.08000.055*
C300.2331 (3)0.6538 (3)0.14494 (12)0.0444 (8)
C310.1107 (2)0.6394 (3)0.13184 (12)0.0487 (9)
H310.09400.56700.13800.058*
C270.4588 (3)0.6670 (3)0.16988 (14)0.0571 (10)
O4−0.3110 (2)0.6600 (2)0.09749 (10)0.0798 (9)
C370.0296 (3)0.7010 (4)0.16343 (15)0.0713 (13)
H37A0.04620.77360.16040.086*
H37B0.04080.68180.19660.086*
C44−0.0779 (3)0.6321 (3)0.01750 (12)0.0517 (9)
H44A−0.05570.69400.00070.062*
H44B−0.05390.5726−0.00060.062*
C340.2893 (3)0.6290 (3)0.05843 (12)0.0545 (10)
H34A0.34050.57860.04530.065*
H34B0.30130.69310.04150.065*
C280.3778 (3)0.6752 (3)0.20437 (15)0.0655 (11)
H280.39780.68510.23620.079*
C330.1711 (3)0.5936 (3)0.04966 (12)0.0512 (9)
H33A0.15340.60050.01590.061*
H33B0.16430.52170.05820.061*
C43−0.2025 (3)0.6300 (3)0.02647 (14)0.0548 (9)
C45−0.2860 (3)0.5952 (3)−0.00045 (14)0.0592 (10)
H45−0.35570.59480.01430.071*
C350.3160 (3)0.6445 (3)0.11030 (12)0.0453 (8)
C41−0.1050 (3)0.8121 (3)0.08368 (15)0.0709 (12)
H41A−0.16020.84980.10140.106*
H41B−0.11860.81990.05000.106*
H41C−0.03200.83790.09130.106*
C290.2674 (3)0.6686 (3)0.19177 (13)0.0587 (10)
H290.21350.67440.21560.070*
C42−0.2216 (3)0.6622 (3)0.07671 (14)0.0575 (10)
C39−0.1118 (3)0.6975 (3)0.09718 (14)0.0510 (10)
C47−0.2059 (4)0.5875 (3)−0.08312 (16)0.0723 (12)
H47−0.14830.6313−0.07400.087*
C38−0.0934 (3)0.6821 (4)0.14968 (14)0.0695 (12)
H38A−0.11420.61250.15830.083*
H38B−0.14090.72890.16740.083*
C48−0.2113 (4)0.5541 (4)−0.12928 (18)0.0925 (15)
H48−0.15930.5788−0.15120.111*
C46−0.2847 (3)0.5574 (3)−0.04950 (15)0.0604 (11)
C49−0.2898 (5)0.4861 (4)−0.14458 (18)0.0908 (15)
C51−0.3674 (4)0.4912 (4)−0.06468 (19)0.0855 (14)
H51−0.42340.4712−0.04350.103*
C50−0.3677 (4)0.4536 (4)−0.11210 (19)0.0962 (17)
H50−0.42160.4062−0.12140.115*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S20.266 (3)0.177 (2)0.0823 (12)−0.066 (2)−0.0282 (14)0.0141 (12)
C520.152 (7)0.215 (10)0.224 (9)0.006 (7)0.053 (6)0.111 (8)
S10.0891 (7)0.0926 (9)0.0500 (6)0.0235 (7)0.0109 (6)0.0077 (6)
C100.0372 (17)0.058 (3)0.049 (2)0.0036 (17)−0.0041 (16)0.0086 (18)
C10.0393 (18)0.047 (2)0.051 (2)0.0058 (16)0.0015 (16)0.0093 (17)
C40.0404 (17)0.042 (2)0.043 (2)−0.0010 (16)0.0019 (15)0.0042 (15)
O10.0374 (13)0.084 (2)0.0597 (17)−0.0024 (13)0.0078 (11)0.0178 (15)
C110.0418 (17)0.065 (3)0.040 (2)−0.0021 (18)−0.0088 (15)0.0044 (18)
C180.0374 (18)0.078 (3)0.041 (2)−0.0095 (18)0.0011 (15)0.0042 (19)
C130.0359 (17)0.047 (2)0.043 (2)−0.0053 (15)−0.0040 (14)0.0111 (17)
C20.0494 (19)0.054 (2)0.043 (2)0.0037 (18)0.0071 (16)0.0108 (17)
C50.0411 (17)0.046 (2)0.040 (2)−0.0003 (16)−0.0070 (15)0.0026 (15)
C30.0474 (19)0.049 (2)0.043 (2)0.0007 (17)−0.0042 (16)−0.0012 (16)
C140.0363 (16)0.045 (2)0.040 (2)−0.0087 (15)−0.0017 (14)0.0021 (15)
C160.0366 (18)0.061 (3)0.052 (2)0.0019 (17)−0.0032 (16)0.0087 (18)
C80.0373 (17)0.098 (3)0.039 (2)0.003 (2)−0.0047 (15)0.010 (2)
O20.0355 (13)0.103 (2)0.0654 (18)−0.0082 (14)−0.0083 (12)0.0224 (15)
C220.075 (3)0.059 (3)0.059 (3)−0.021 (2)0.019 (2)0.000 (2)
C200.0408 (19)0.055 (2)0.050 (2)0.0003 (17)0.0100 (16)0.0024 (18)
C60.0360 (16)0.048 (2)0.039 (2)−0.0029 (16)−0.0007 (14)0.0047 (16)
C120.0400 (18)0.070 (3)0.047 (2)−0.0071 (18)−0.0084 (15)0.0100 (19)
C190.0401 (19)0.066 (3)0.050 (2)−0.0013 (18)−0.0021 (16)0.0046 (18)
C240.052 (2)0.103 (4)0.049 (3)−0.007 (2)0.0033 (18)−0.002 (2)
C170.0352 (17)0.056 (2)0.051 (2)−0.0028 (16)0.0036 (16)0.0068 (18)
C90.0401 (18)0.052 (2)0.038 (2)0.0042 (17)−0.0036 (14)−0.0014 (17)
C70.0399 (18)0.079 (3)0.047 (2)0.0043 (19)−0.0008 (15)0.015 (2)
C230.059 (2)0.062 (3)0.046 (2)0.015 (2)0.011 (2)−0.0047 (19)
C250.059 (2)0.080 (3)0.054 (3)−0.020 (2)0.0096 (19)−0.004 (2)
C150.054 (2)0.055 (3)0.076 (3)0.0048 (19)0.0101 (19)0.011 (2)
C210.057 (2)0.081 (3)0.052 (3)−0.019 (2)0.0031 (19)0.001 (2)
C260.117 (4)0.077 (3)0.074 (3)0.010 (3)0.033 (3)0.018 (2)
C360.046 (2)0.049 (2)0.060 (3)0.0026 (17)−0.0006 (17)−0.0064 (19)
O30.0513 (15)0.084 (2)0.093 (2)−0.0072 (16)−0.0204 (14)−0.0098 (19)
C320.0381 (16)0.039 (2)0.050 (2)0.0018 (16)0.0023 (15)−0.0007 (16)
C400.0375 (17)0.038 (2)0.061 (2)−0.0016 (15)−0.0020 (16)0.0011 (17)
C300.0427 (18)0.042 (2)0.048 (2)−0.0037 (17)0.0020 (16)−0.0010 (17)
C310.0423 (18)0.052 (2)0.052 (2)−0.0063 (17)0.0039 (15)−0.0015 (18)
C270.047 (2)0.055 (3)0.069 (3)−0.0088 (19)−0.012 (2)−0.004 (2)
O40.0393 (14)0.102 (2)0.098 (2)−0.0063 (16)0.0093 (14)−0.0180 (18)
C370.049 (2)0.105 (4)0.060 (3)0.002 (2)0.0116 (18)−0.020 (2)
C440.0417 (18)0.052 (2)0.061 (2)0.0005 (17)−0.0034 (16)−0.0047 (18)
C340.0405 (18)0.068 (3)0.055 (2)0.0065 (18)0.0024 (16)−0.0060 (19)
C280.063 (3)0.078 (3)0.056 (3)−0.013 (2)−0.014 (2)−0.009 (2)
C330.0415 (18)0.060 (2)0.052 (2)0.0012 (18)−0.0022 (16)−0.0078 (17)
C430.0424 (19)0.048 (2)0.074 (3)0.0036 (17)−0.0044 (18)0.0006 (19)
C450.041 (2)0.061 (3)0.076 (3)−0.0011 (18)−0.0092 (18)0.005 (2)
C350.0393 (17)0.041 (2)0.055 (2)−0.0013 (17)−0.0026 (16)0.0007 (16)
C410.056 (2)0.048 (3)0.109 (4)0.009 (2)0.002 (2)−0.012 (2)
C290.058 (2)0.066 (3)0.052 (3)−0.009 (2)0.0023 (18)−0.004 (2)
C420.0329 (19)0.054 (2)0.085 (3)−0.0016 (17)0.0021 (18)−0.004 (2)
C390.0396 (18)0.050 (3)0.063 (3)0.0009 (17)0.0054 (16)−0.0060 (18)
C470.066 (3)0.070 (3)0.081 (3)0.005 (2)−0.010 (2)0.002 (2)
C380.043 (2)0.097 (4)0.068 (3)−0.005 (2)0.0153 (19)−0.017 (2)
C480.094 (4)0.105 (4)0.078 (4)0.000 (3)−0.011 (3)0.010 (3)
C460.049 (2)0.054 (3)0.078 (3)0.007 (2)−0.018 (2)0.011 (2)
C490.105 (4)0.090 (4)0.078 (3)−0.006 (3)−0.018 (3)0.013 (3)
C510.067 (3)0.094 (4)0.096 (4)−0.018 (3)−0.033 (3)0.019 (3)
C500.109 (4)0.090 (4)0.089 (4)−0.029 (3)−0.056 (3)0.009 (3)

Geometric parameters (Å, °)

S2—C521.562 (8)C15—H15C0.9600
S2—C491.794 (6)C21—H210.9300
C52—H52A0.9600C26—H26A0.9600
C52—H52B0.9600C26—H26B0.9600
C52—H52C0.9600C26—H26C0.9600
S1—C261.754 (5)C36—C271.362 (5)
S1—C231.756 (4)C36—C351.393 (5)
C10—C11.369 (5)C36—H360.9300
C10—C91.389 (4)O3—C271.373 (4)
C10—H100.9300O3—H3A0.8200
C1—O11.366 (4)C32—C331.501 (4)
C1—C21.384 (5)C32—C401.518 (4)
C4—C31.388 (4)C32—C311.521 (4)
C4—C91.395 (4)C32—H320.9800
C4—C51.526 (4)C40—C441.527 (5)
O1—H10.8200C40—C391.530 (5)
C11—C51.532 (4)C40—H400.9800
C11—C121.532 (4)C30—C291.385 (5)
C11—H11A0.9700C30—C351.391 (4)
C11—H11B0.9700C30—C311.521 (4)
C18—C171.505 (4)C31—C371.537 (5)
C18—C141.517 (4)C31—H310.9800
C18—H18A0.9700C27—C281.371 (5)
C18—H18B0.9700O4—C421.218 (4)
C13—C121.506 (5)C37—C381.541 (5)
C13—C161.513 (5)C37—H37A0.9700
C13—C151.530 (5)C37—H37B0.9700
C13—C141.542 (4)C44—C431.511 (5)
C2—C31.383 (4)C44—H44A0.9700
C2—H20.9300C44—H44B0.9700
C5—C61.514 (4)C34—C351.498 (5)
C5—H50.9800C34—C331.508 (4)
C3—H30.9300C34—H34A0.9700
C14—C61.521 (4)C34—H34B0.9700
C14—H140.9800C28—C291.370 (5)
C16—O21.227 (4)C28—H280.9300
C16—C171.464 (5)C33—H33A0.9700
C8—C71.506 (5)C33—H33B0.9700
C8—C91.513 (4)C43—C451.331 (5)
C8—H8A0.9700C43—C421.483 (5)
C8—H8B0.9700C45—C461.456 (5)
C22—C231.357 (5)C45—H450.9300
C22—C211.390 (5)C41—C391.542 (5)
C22—H220.9300C41—H41A0.9600
C20—C211.377 (5)C41—H41B0.9600
C20—C251.389 (5)C41—H41C0.9600
C20—C191.448 (5)C29—H290.9300
C6—C71.521 (4)C42—C391.505 (5)
C6—H60.9800C39—C381.497 (5)
C12—H12A0.9700C47—C481.363 (6)
C12—H12B0.9700C47—C461.388 (5)
C19—C171.335 (4)C47—H470.9300
C19—H190.9300C38—H38A0.9700
C24—C251.349 (5)C38—H38B0.9700
C24—C231.377 (5)C48—C491.360 (7)
C24—H240.9300C48—H480.9300
C7—H7A0.9700C46—C511.380 (6)
C7—H7B0.9700C49—C501.368 (7)
C25—H250.9300C51—C501.413 (7)
C15—H15A0.9600C51—H510.9300
C15—H15B0.9600C50—H500.9300
C52—S2—C4997.0 (4)C22—C21—H21119.3
S2—C52—H52A109.5S1—C26—H26A109.5
S2—C52—H52B109.5S1—C26—H26B109.5
H52A—C52—H52B109.5H26A—C26—H26B109.5
S2—C52—H52C109.5S1—C26—H26C109.5
H52A—C52—H52C109.5H26A—C26—H26C109.5
H52B—C52—H52C109.5H26B—C26—H26C109.5
C26—S1—C23104.4 (2)C27—C36—C35121.6 (3)
C1—C10—C9121.9 (3)C27—C36—H36119.2
C1—C10—H10119.0C35—C36—H36119.2
C9—C10—H10119.0C27—O3—H3A109.5
O1—C1—C10123.3 (3)C33—C32—C40113.4 (3)
O1—C1—C2117.6 (3)C33—C32—C31110.3 (3)
C10—C1—C2119.1 (3)C40—C32—C31108.0 (3)
C3—C4—C9117.7 (3)C33—C32—H32108.3
C3—C4—C5121.5 (3)C40—C32—H32108.3
C9—C4—C5120.8 (3)C31—C32—H32108.3
C1—O1—H1109.5C32—C40—C44121.4 (3)
C5—C11—C12112.3 (3)C32—C40—C39112.1 (3)
C5—C11—H11A109.1C44—C40—C39104.5 (3)
C12—C11—H11A109.1C32—C40—H40105.9
C5—C11—H11B109.1C44—C40—H40105.9
C12—C11—H11B109.1C39—C40—H40105.9
H11A—C11—H11B107.9C29—C30—C35117.3 (3)
C17—C18—C14102.3 (3)C29—C30—C31122.0 (3)
C17—C18—H18A111.3C35—C30—C31120.5 (3)
C14—C18—H18A111.3C30—C31—C32112.0 (3)
C17—C18—H18B111.3C30—C31—C37113.9 (3)
C14—C18—H18B111.3C32—C31—C37112.7 (3)
H18A—C18—H18B109.2C30—C31—H31105.8
C12—C13—C16118.3 (3)C32—C31—H31105.8
C12—C13—C15112.0 (3)C37—C31—H31105.8
C16—C13—C15104.8 (3)C36—C27—C28119.2 (3)
C12—C13—C14108.3 (3)C36—C27—O3123.1 (4)
C16—C13—C1499.8 (3)C28—C27—O3117.6 (3)
C15—C13—C14113.2 (3)C31—C37—C38112.1 (3)
C3—C2—C1119.3 (3)C31—C37—H37A109.2
C3—C2—H2120.3C38—C37—H37A109.2
C1—C2—H2120.3C31—C37—H37B109.2
C6—C5—C4111.9 (3)C38—C37—H37B109.2
C6—C5—C11111.7 (3)H37A—C37—H37B107.9
C4—C5—C11114.2 (3)C43—C44—C40101.8 (3)
C6—C5—H5106.1C43—C44—H44A111.4
C4—C5—H5106.1C40—C44—H44A111.4
C11—C5—H5106.1C43—C44—H44B111.4
C2—C3—C4122.3 (3)C40—C44—H44B111.4
C2—C3—H3118.8H44A—C44—H44B109.3
C4—C3—H3118.8C35—C34—C33113.5 (3)
C18—C14—C6122.4 (3)C35—C34—H34A108.9
C18—C14—C13105.2 (3)C33—C34—H34A108.9
C6—C14—C13111.5 (3)C35—C34—H34B108.9
C18—C14—H14105.5C33—C34—H34B108.9
C6—C14—H14105.5H34A—C34—H34B107.7
C13—C14—H14105.5C29—C28—C27119.8 (4)
O2—C16—C17125.8 (3)C29—C28—H28120.1
O2—C16—C13125.3 (3)C27—C28—H28120.1
C17—C16—C13108.9 (3)C32—C33—C34110.7 (3)
C7—C8—C9113.5 (3)C32—C33—H33A109.5
C7—C8—H8A108.9C34—C33—H33A109.5
C9—C8—H8A108.9C32—C33—H33B109.5
C7—C8—H8B108.9C34—C33—H33B109.5
C9—C8—H8B108.9H33A—C33—H33B108.1
H8A—C8—H8B107.7C45—C43—C42121.0 (3)
C23—C22—C21120.8 (4)C45—C43—C44130.7 (4)
C23—C22—H22119.6C42—C43—C44107.7 (3)
C21—C22—H22119.6C43—C45—C46129.8 (4)
C21—C20—C25116.4 (3)C43—C45—H45115.1
C21—C20—C19120.4 (3)C46—C45—H45115.1
C25—C20—C19123.1 (3)C30—C35—C36119.6 (3)
C5—C6—C7110.6 (3)C30—C35—C34122.2 (3)
C5—C6—C14108.0 (3)C36—C35—C34118.1 (3)
C7—C6—C14113.0 (3)C39—C41—H41A109.5
C5—C6—H6108.4C39—C41—H41B109.5
C7—C6—H6108.4H41A—C41—H41B109.5
C14—C6—H6108.4C39—C41—H41C109.5
C13—C12—C11111.1 (3)H41A—C41—H41C109.5
C13—C12—H12A109.4H41B—C41—H41C109.5
C11—C12—H12A109.4C28—C29—C30122.5 (4)
C13—C12—H12B109.4C28—C29—H29118.7
C11—C12—H12B109.4C30—C29—H29118.7
H12A—C12—H12B108.0O4—C42—C43125.5 (3)
C17—C19—C20128.4 (3)O4—C42—C39126.4 (4)
C17—C19—H19115.8C43—C42—C39108.1 (3)
C20—C19—H19115.8C38—C39—C42117.4 (3)
C25—C24—C23121.9 (4)C38—C39—C40110.3 (3)
C25—C24—H24119.1C42—C39—C40100.0 (3)
C23—C24—H24119.1C38—C39—C41111.2 (3)
C19—C17—C16122.1 (3)C42—C39—C41104.4 (3)
C19—C17—C18129.4 (3)C40—C39—C41113.2 (3)
C16—C17—C18108.3 (3)C48—C47—C46121.2 (5)
C10—C9—C4119.7 (3)C48—C47—H47119.4
C10—C9—C8118.3 (3)C46—C47—H47119.4
C4—C9—C8122.0 (3)C39—C38—C37111.3 (3)
C8—C7—C6110.0 (3)C39—C38—H38A109.4
C8—C7—H7A109.7C37—C38—H38A109.4
C6—C7—H7A109.7C39—C38—H38B109.4
C8—C7—H7B109.7C37—C38—H38B109.4
C6—C7—H7B109.7H38A—C38—H38B108.0
H7A—C7—H7B108.2C49—C48—C47122.6 (5)
C22—C23—C24117.8 (4)C49—C48—H48118.7
C22—C23—S1125.6 (3)C47—C48—H48118.7
C24—C23—S1116.6 (3)C51—C46—C47117.1 (4)
C24—C25—C20121.6 (4)C51—C46—C45119.5 (4)
C24—C25—H25119.2C47—C46—C45123.3 (4)
C20—C25—H25119.2C48—C49—C50117.6 (5)
C13—C15—H15A109.5C48—C49—S2116.3 (4)
C13—C15—H15B109.5C50—C49—S2126.0 (4)
H15A—C15—H15B109.5C46—C51—C50120.4 (5)
C13—C15—H15C109.5C46—C51—H51119.8
H15A—C15—H15C109.5C50—C51—H51119.8
H15B—C15—H15C109.5C49—C50—C51120.9 (5)
C20—C21—C22121.5 (4)C49—C50—H50119.6
C20—C21—H21119.3C51—C50—H50119.6
C9—C10—C1—O1179.9 (3)C33—C32—C40—C44−53.6 (4)
C9—C10—C1—C2−0.9 (6)C31—C32—C40—C44−176.1 (3)
O1—C1—C2—C3179.0 (3)C33—C32—C40—C39−178.0 (3)
C10—C1—C2—C3−0.2 (5)C31—C32—C40—C3959.5 (4)
C3—C4—C5—C6162.7 (3)C29—C30—C31—C32163.3 (3)
C9—C4—C5—C6−19.3 (5)C35—C30—C31—C32−21.8 (5)
C3—C4—C5—C1134.4 (5)C29—C30—C31—C3734.0 (5)
C9—C4—C5—C11−147.6 (3)C35—C30—C31—C37−151.1 (4)
C12—C11—C5—C653.5 (4)C33—C32—C31—C3050.3 (4)
C12—C11—C5—C4−178.1 (3)C40—C32—C31—C30174.8 (3)
C1—C2—C3—C40.8 (6)C33—C32—C31—C37−179.7 (3)
C9—C4—C3—C2−0.3 (5)C40—C32—C31—C37−55.3 (4)
C5—C4—C3—C2177.8 (3)C35—C36—C27—C28−1.5 (6)
C17—C18—C14—C6−164.5 (3)C35—C36—C27—O3176.1 (4)
C17—C18—C14—C13−36.0 (4)C30—C31—C37—C38−178.6 (3)
C12—C13—C14—C18163.1 (3)C32—C31—C37—C3852.4 (5)
C16—C13—C14—C1838.8 (3)C32—C40—C44—C43−165.7 (3)
C15—C13—C14—C18−72.0 (3)C39—C40—C44—C43−37.9 (3)
C12—C13—C14—C6−62.2 (4)C36—C27—C28—C290.4 (7)
C16—C13—C14—C6173.5 (3)O3—C27—C28—C29−177.4 (4)
C15—C13—C14—C662.7 (4)C40—C32—C33—C34175.1 (3)
C12—C13—C16—O238.0 (6)C31—C32—C33—C34−63.6 (4)
C15—C13—C16—O2−87.6 (5)C35—C34—C33—C3245.8 (4)
C14—C13—C16—O2155.0 (4)C40—C44—C43—C45−153.0 (4)
C12—C13—C16—C17−144.2 (3)C40—C44—C43—C4218.8 (4)
C15—C13—C16—C1790.1 (3)C42—C43—C45—C46−178.1 (4)
C14—C13—C16—C17−27.2 (4)C44—C43—C45—C46−7.3 (7)
C4—C5—C6—C750.0 (4)C29—C30—C35—C36−1.7 (5)
C11—C5—C6—C7179.6 (3)C31—C30—C35—C36−177.0 (3)
C4—C5—C6—C14174.1 (3)C29—C30—C35—C34−179.6 (3)
C11—C5—C6—C14−56.3 (4)C31—C30—C35—C345.2 (5)
C18—C14—C6—C5−172.8 (3)C27—C36—C35—C302.3 (6)
C13—C14—C6—C561.5 (4)C27—C36—C35—C34−179.8 (3)
C18—C14—C6—C7−50.1 (5)C33—C34—C35—C30−17.2 (5)
C13—C14—C6—C7−175.8 (3)C33—C34—C35—C36165.0 (3)
C16—C13—C12—C11168.9 (3)C27—C28—C29—C300.1 (7)
C15—C13—C12—C11−69.1 (4)C35—C30—C29—C280.6 (6)
C14—C13—C12—C1156.5 (4)C31—C30—C29—C28175.8 (4)
C5—C11—C12—C13−53.6 (4)C45—C43—C42—O40.1 (6)
C21—C20—C19—C17158.8 (4)C44—C43—C42—O4−172.6 (4)
C25—C20—C19—C17−21.5 (6)C45—C43—C42—C39180.0 (4)
C20—C19—C17—C16−177.9 (4)C44—C43—C42—C397.3 (4)
C20—C19—C17—C18−3.9 (7)O4—C42—C39—C3830.7 (6)
O2—C16—C17—C19−1.2 (6)C43—C42—C39—C38−149.1 (3)
C13—C16—C17—C19−179.0 (4)O4—C42—C39—C40149.9 (4)
O2—C16—C17—C18−176.3 (4)C43—C42—C39—C40−29.9 (4)
C13—C16—C17—C185.9 (4)O4—C42—C39—C41−92.9 (5)
C14—C18—C17—C19−156.0 (4)C43—C42—C39—C4187.3 (3)
C14—C18—C17—C1618.6 (4)C32—C40—C39—C38−60.6 (4)
C1—C10—C9—C41.5 (6)C44—C40—C39—C38166.1 (3)
C1—C10—C9—C8−179.1 (4)C32—C40—C39—C42175.1 (3)
C3—C4—C9—C10−0.8 (5)C44—C40—C39—C4241.8 (4)
C5—C4—C9—C10−178.9 (3)C32—C40—C39—C4164.6 (4)
C3—C4—C9—C8179.7 (3)C44—C40—C39—C41−68.7 (4)
C5—C4—C9—C81.6 (5)C42—C39—C38—C37168.4 (4)
C7—C8—C9—C10165.4 (3)C40—C39—C38—C3754.8 (4)
C7—C8—C9—C4−15.2 (5)C41—C39—C38—C37−71.5 (4)
C9—C8—C7—C645.5 (5)C31—C37—C38—C39−51.5 (5)
C5—C6—C7—C8−64.4 (4)C46—C47—C48—C49−3.4 (7)
C14—C6—C7—C8174.4 (3)C48—C47—C46—C511.0 (6)
C21—C22—C23—C24−0.4 (6)C48—C47—C46—C45−176.7 (4)
C21—C22—C23—S1179.1 (3)C43—C45—C46—C51155.9 (4)
C25—C24—C23—C221.5 (6)C43—C45—C46—C47−26.5 (6)
C25—C24—C23—S1−178.0 (3)C47—C48—C49—C502.2 (8)
C26—S1—C23—C2218.8 (4)C47—C48—C49—S2−179.6 (4)
C26—S1—C23—C24−161.7 (3)C52—S2—C49—C48167.6 (5)
C23—C24—C25—C20−0.3 (7)C52—S2—C49—C50−14.4 (6)
C21—C20—C25—C24−2.0 (6)C47—C46—C51—C502.3 (6)
C19—C20—C25—C24178.3 (4)C45—C46—C51—C50−179.9 (4)
C25—C20—C21—C223.0 (6)C48—C49—C50—C511.2 (8)
C19—C20—C21—C22−177.3 (4)S2—C49—C50—C51−176.8 (4)
C23—C22—C21—C20−1.9 (6)C46—C51—C50—C49−3.5 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C19—H19···O20.932.572.894 (4)101
C45—H45···O40.932.532.880 (5)103
O1—H1···O2i0.821.952.746 (3)163
C10—H10···O2i0.932.533.179 (4)127
O3—H3A···O4ii0.822.032.830 (4)166
C36—H36···O4ii0.932.473.209 (4)136

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2822).

References

  • Alvarez-Ginarte, Y. M., Crespo, R., Montero-Cabrera, L. A., Ruiz-Garcia, J. A., Ponce, Y. M., Santana, R., Pardillo-Fontdevila, E. & Alonso-Becerra, E. (2005). QSAR Comb. Sci.24, 218–226.
  • Bruker (2004). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc.97, 1354–1358.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Suitchmezian, V., Jess, I. & Näther, C. (2007). Acta Cryst. E63, o4839.
  • Ye, Y.-Y. (2007). Acta Cryst. E63, o3022.

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