organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(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

aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India, bDepartment of Analytical Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and cReader in Physics, Presidency College, Chennai 600 005, India
*Correspondence e-mail: manivan_1999@yahoo.com

(Received 27 November 2008; accepted 3 December 2008; online 10 December 2008)

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[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.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For related structures, see: Suitchmezian et al. (2007[Suitchmezian, V., Jess, I. & Näther, C. (2007). Acta Cryst. E63, o4839.]); Ye (2007[Ye, Y.-Y. (2007). Acta Cryst. E63, o3022.]).

[Scheme 1]

Experimental

Crystal data
  • C26H28O2S

  • Mr = 404.54

  • Orthorhombic, P 21 21 21

  • 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[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.959, Tmax = 0.975

  • 21727 measured reflections

  • 6847 independent reflections

  • 4775 reflections with I > 2σ(I)

  • Rint = 0.040

  • θmax = 24.1°

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2995 Friedel pairs

  • Flack parameter: −0.06 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O2i 0.82 1.95 2.746 (3) 163
C10—H10⋯O2i 0.93 2.53 3.179 (4) 127
O3—H3A⋯O4ii 0.82 2.03 2.830 (4) 166
C36—H36⋯O4ii 0.93 2.47 3.209 (4) 136
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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.

Related literature top

For the biological activity of testosterone derivatives, see: Alvarez-Ginarte et al. (2005). For puckering parameters, see: Cremer & Pople (1975). For related structures, see: Suitchmezian et al. (2007); Ye (2007).[Please provide new scheme; cyclopentane is fused at the wrong position]

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of the title compound, viewed down the b axis. Hydrogen bonds are shown as dashed lines.
(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 top
Crystal data top
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 top
Bruker Kappa APEXII
diffractometer
6847 independent reflections
Radiation source: fine-focus sealed tube4775 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 0 pixels mm-1θmax = 24.1°, θmin = 1.5°
ω and ϕ scansh = 1313
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1414
Tmin = 0.959, Tmax = 0.975l = 2332
21727 measured 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)] = 0.049H-atom parameters constrained
wR(F2) = 0.142 w = 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 = 0.30 e Å3
0 restraintsAbsolute structure: Flack (1983), 2995 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (11)
Crystal data top
C26H28O2SV = 4355.5 (2) Å3
Mr = 404.54Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 11.9654 (3) ŵ = 0.17 mm1
b = 13.0262 (4) ÅT = 293 K
c = 27.9441 (8) Å0.25 × 0.20 × 0.15 mm
Data collection top
Bruker Kappa APEXII
diffractometer
6847 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4775 reflections with I > 2σ(I)
Tmin = 0.959, Tmax = 0.975Rint = 0.040
21727 measured reflectionsθmax = 24.1°
Refinement top
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.142Δρmax = 0.38 e Å3
S = 1.06Δρmin = 0.30 e Å3
6847 reflectionsAbsolute structure: Flack (1983), 2995 Friedel pairs
529 parametersAbsolute structure parameter: 0.06 (11)
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S20.2835 (2)0.45026 (18)0.20650 (6)0.1751 (10)
C520.3659 (6)0.3576 (7)0.2034 (3)0.197 (4)
H52A0.34430.31350.17750.296*
H52B0.36390.31980.23290.296*
H52C0.44030.38250.19800.296*
S10.68074 (10)0.04257 (9)0.06634 (4)0.0772 (4)
C100.0077 (3)0.1662 (3)0.39329 (13)0.0480 (9)
H100.04520.17520.36930.058*
C10.0260 (2)0.1691 (3)0.44008 (13)0.0457 (9)
C40.1992 (3)0.1388 (3)0.41632 (11)0.0419 (8)
O10.13439 (17)0.1845 (2)0.45361 (9)0.0603 (7)
H10.17530.17950.43020.090*
C110.4053 (2)0.1657 (3)0.43880 (12)0.0490 (9)
H11A0.39550.23960.43960.059*
H11B0.39010.13940.47060.059*
C180.5165 (2)0.1240 (3)0.29171 (11)0.0522 (10)
H18A0.49950.18950.27690.063*
H18B0.48960.06900.27130.063*
C130.5510 (2)0.1717 (3)0.37447 (12)0.0421 (8)
C20.0528 (3)0.1572 (3)0.47588 (12)0.0487 (9)
H20.03150.15870.50790.058*
C50.3214 (3)0.1193 (3)0.40352 (11)0.0422 (8)
H50.33190.04470.40520.051*
C30.1637 (3)0.1429 (3)0.46359 (11)0.0464 (9)
H30.21640.13580.48780.056*
C140.4667 (2)0.1169 (3)0.34152 (11)0.0405 (8)
H140.47080.04410.35020.049*
C160.6593 (3)0.1357 (3)0.35210 (12)0.0499 (9)
C80.1480 (3)0.1465 (4)0.32801 (11)0.0582 (11)
H8A0.14430.21550.31500.070*
H8B0.09280.10530.31140.070*
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)
H60.34280.22440.34990.049*
C120.5265 (2)0.1411 (3)0.42538 (12)0.0523 (10)
H12A0.53970.06810.42920.063*
H12B0.57660.17740.44680.063*
C190.7213 (3)0.0814 (3)0.27246 (12)0.0523 (9)
H190.79190.07650.28620.063*
C240.6231 (3)0.0568 (4)0.14629 (14)0.0676 (12)
H240.56460.08070.12740.081*
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)
H7A0.26080.02890.32220.066*
H7B0.28380.11770.28550.066*
C230.7015 (3)0.0076 (3)0.12637 (13)0.0556 (10)
C250.6286 (3)0.0864 (3)0.19251 (14)0.0644 (11)
H250.57380.12980.20460.077*
C150.5518 (3)0.2884 (3)0.36806 (14)0.0617 (11)
H15A0.56120.30470.33480.093*
H15B0.48230.31640.37920.093*
H15C0.61230.31740.38610.093*
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*
C400.0314 (2)0.6301 (3)0.06840 (12)0.0454 (8)
H400.04260.55990.08000.055*
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)
O40.3110 (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*
C440.0779 (3)0.6321 (3)0.01750 (12)0.0517 (9)
H44A0.05570.69400.00070.062*
H44B0.05390.57260.00060.062*
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*
C430.2025 (3)0.6300 (3)0.02647 (14)0.0548 (9)
C450.2860 (3)0.5952 (3)0.00045 (14)0.0592 (10)
H450.35570.59480.01430.071*
C350.3160 (3)0.6445 (3)0.11030 (12)0.0453 (8)
C410.1050 (3)0.8121 (3)0.08368 (15)0.0709 (12)
H41A0.16020.84980.10140.106*
H41B0.11860.81990.05000.106*
H41C0.03200.83790.09130.106*
C290.2674 (3)0.6686 (3)0.19177 (13)0.0587 (10)
H290.21350.67440.21560.070*
C420.2216 (3)0.6622 (3)0.07671 (14)0.0575 (10)
C390.1118 (3)0.6975 (3)0.09718 (14)0.0510 (10)
C470.2059 (4)0.5875 (3)0.08312 (16)0.0723 (12)
H470.14830.63130.07400.087*
C380.0934 (3)0.6821 (4)0.14968 (14)0.0695 (12)
H38A0.11420.61250.15830.083*
H38B0.14090.72890.16740.083*
C480.2113 (4)0.5541 (4)0.12928 (18)0.0925 (15)
H480.15930.57880.15120.111*
C460.2847 (3)0.5574 (3)0.04950 (15)0.0604 (11)
C490.2898 (5)0.4861 (4)0.14458 (18)0.0908 (15)
C510.3674 (4)0.4912 (4)0.06468 (19)0.0855 (14)
H510.42340.47120.04350.103*
C500.3677 (4)0.4536 (4)0.11210 (19)0.0962 (17)
H500.42160.40620.12140.115*
Atomic displacement parameters (Å2) top
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, º) top
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—C4453.6 (4)
C9—C10—C1—C20.9 (6)C31—C32—C40—C44176.1 (3)
O1—C1—C2—C3179.0 (3)C33—C32—C40—C39178.0 (3)
C10—C1—C2—C30.2 (5)C31—C32—C40—C3959.5 (4)
C3—C4—C5—C6162.7 (3)C29—C30—C31—C32163.3 (3)
C9—C4—C5—C619.3 (5)C35—C30—C31—C3221.8 (5)
C3—C4—C5—C1134.4 (5)C29—C30—C31—C3734.0 (5)
C9—C4—C5—C11147.6 (3)C35—C30—C31—C37151.1 (4)
C12—C11—C5—C653.5 (4)C33—C32—C31—C3050.3 (4)
C12—C11—C5—C4178.1 (3)C40—C32—C31—C30174.8 (3)
C1—C2—C3—C40.8 (6)C33—C32—C31—C37179.7 (3)
C9—C4—C3—C20.3 (5)C40—C32—C31—C3755.3 (4)
C5—C4—C3—C2177.8 (3)C35—C36—C27—C281.5 (6)
C17—C18—C14—C6164.5 (3)C35—C36—C27—O3176.1 (4)
C17—C18—C14—C1336.0 (4)C30—C31—C37—C38178.6 (3)
C12—C13—C14—C18163.1 (3)C32—C31—C37—C3852.4 (5)
C16—C13—C14—C1838.8 (3)C32—C40—C44—C43165.7 (3)
C15—C13—C14—C1872.0 (3)C39—C40—C44—C4337.9 (3)
C12—C13—C14—C662.2 (4)C36—C27—C28—C290.4 (7)
C16—C13—C14—C6173.5 (3)O3—C27—C28—C29177.4 (4)
C15—C13—C14—C662.7 (4)C40—C32—C33—C34175.1 (3)
C12—C13—C16—O238.0 (6)C31—C32—C33—C3463.6 (4)
C15—C13—C16—O287.6 (5)C35—C34—C33—C3245.8 (4)
C14—C13—C16—O2155.0 (4)C40—C44—C43—C45153.0 (4)
C12—C13—C16—C17144.2 (3)C40—C44—C43—C4218.8 (4)
C15—C13—C16—C1790.1 (3)C42—C43—C45—C46178.1 (4)
C14—C13—C16—C1727.2 (4)C44—C43—C45—C467.3 (7)
C4—C5—C6—C750.0 (4)C29—C30—C35—C361.7 (5)
C11—C5—C6—C7179.6 (3)C31—C30—C35—C36177.0 (3)
C4—C5—C6—C14174.1 (3)C29—C30—C35—C34179.6 (3)
C11—C5—C6—C1456.3 (4)C31—C30—C35—C345.2 (5)
C18—C14—C6—C5172.8 (3)C27—C36—C35—C302.3 (6)
C13—C14—C6—C561.5 (4)C27—C36—C35—C34179.8 (3)
C18—C14—C6—C750.1 (5)C33—C34—C35—C3017.2 (5)
C13—C14—C6—C7175.8 (3)C33—C34—C35—C36165.0 (3)
C16—C13—C12—C11168.9 (3)C27—C28—C29—C300.1 (7)
C15—C13—C12—C1169.1 (4)C35—C30—C29—C280.6 (6)
C14—C13—C12—C1156.5 (4)C31—C30—C29—C28175.8 (4)
C5—C11—C12—C1353.6 (4)C45—C43—C42—O40.1 (6)
C21—C20—C19—C17158.8 (4)C44—C43—C42—O4172.6 (4)
C25—C20—C19—C1721.5 (6)C45—C43—C42—C39180.0 (4)
C20—C19—C17—C16177.9 (4)C44—C43—C42—C397.3 (4)
C20—C19—C17—C183.9 (7)O4—C42—C39—C3830.7 (6)
O2—C16—C17—C191.2 (6)C43—C42—C39—C38149.1 (3)
C13—C16—C17—C19179.0 (4)O4—C42—C39—C40149.9 (4)
O2—C16—C17—C18176.3 (4)C43—C42—C39—C4029.9 (4)
C13—C16—C17—C185.9 (4)O4—C42—C39—C4192.9 (5)
C14—C18—C17—C19156.0 (4)C43—C42—C39—C4187.3 (3)
C14—C18—C17—C1618.6 (4)C32—C40—C39—C3860.6 (4)
C1—C10—C9—C41.5 (6)C44—C40—C39—C38166.1 (3)
C1—C10—C9—C8179.1 (4)C32—C40—C39—C42175.1 (3)
C3—C4—C9—C100.8 (5)C44—C40—C39—C4241.8 (4)
C5—C4—C9—C10178.9 (3)C32—C40—C39—C4164.6 (4)
C3—C4—C9—C8179.7 (3)C44—C40—C39—C4168.7 (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—C415.2 (5)C41—C39—C38—C3771.5 (4)
C9—C8—C7—C645.5 (5)C31—C37—C38—C3951.5 (5)
C5—C6—C7—C864.4 (4)C46—C47—C48—C493.4 (7)
C14—C6—C7—C8174.4 (3)C48—C47—C46—C511.0 (6)
C21—C22—C23—C240.4 (6)C48—C47—C46—C45176.7 (4)
C21—C22—C23—S1179.1 (3)C43—C45—C46—C51155.9 (4)
C25—C24—C23—C221.5 (6)C43—C45—C46—C4726.5 (6)
C25—C24—C23—S1178.0 (3)C47—C48—C49—C502.2 (8)
C26—S1—C23—C2218.8 (4)C47—C48—C49—S2179.6 (4)
C26—S1—C23—C24161.7 (3)C52—S2—C49—C48167.6 (5)
C23—C24—C25—C200.3 (7)C52—S2—C49—C5014.4 (6)
C21—C20—C25—C242.0 (6)C47—C46—C51—C502.3 (6)
C19—C20—C25—C24178.3 (4)C45—C46—C51—C50179.9 (4)
C25—C20—C21—C223.0 (6)C48—C49—C50—C511.2 (8)
C19—C20—C21—C22177.3 (4)S2—C49—C50—C51176.8 (4)
C23—C22—C21—C201.9 (6)C46—C51—C50—C493.5 (7)
Hydrogen-bond geometry (Å, º) top
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) x1, y, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC26H28O2S
Mr404.54
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)11.9654 (3), 13.0262 (4), 27.9441 (8)
V3)4355.5 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.17
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.959, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
21727, 6847, 4775
Rint0.040
θmax (°)24.1
(sin θ/λ)max1)0.573
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.142, 1.06
No. of reflections6847
No. of parameters529
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.30
Absolute structureFlack (1983), 2995 Friedel pairs
Absolute structure parameter0.06 (11)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
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) x1, y, z; (ii) x+1, y, z.
 

Acknowledgements

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

References

First citationAlvarez-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.  Web of Science CrossRef CAS
First citationBruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science
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