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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1419.
Published online 2008 July 5. doi:  10.1107/S1600536808020254
PMCID: PMC2962053

2-[3,4-Dibut­oxy-5-(5-phenyl-1,3,4-oxadiazol-2-yl)-2-thien­yl]-5-phenyl-1,3,4-oxadiazole

Abstract

In the title compound, C28H28N4O4S, the dihedral angles between the central thio­phene ring and its pendant oxadiazole rings are 1.2 (3) and 9.8 (3)°. The dihedral angles between the oxadiazole and phenyl rings are 2.9 (3) and 1.8 (3)°. Some short intra­molecular C—H(...)O contacts occur.

Related literature

For related literature, see: Bugatti et al. (2006 [triangle]); Brault et al. (2005 [triangle]).

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Object name is e-64-o1419-scheme1.jpg

Experimental

Crystal data

  • C28H28N4O4S
  • M r = 516.60
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1419-efi1.jpg
  • a = 7.6770 (15) Å
  • b = 16.871 (3) Å
  • c = 20.398 (4) Å
  • β = 93.77 (3)°
  • V = 2636.2 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.16 mm−1
  • T = 293 (2) K
  • 0.30 × 0.10 × 0.05 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.953, T max = 0.992
  • 5100 measured reflections
  • 4722 independent reflections
  • 1918 reflections with I > 2σ(I)
  • R int = 0.026
  • 3 standard reflections every 200 reflections intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.087
  • wR(F 2) = 0.203
  • S = 1.00
  • 4722 reflections
  • 328 parameters
  • 216 restraints
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [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/S1600536808020254/hb2756sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020254/hb2756Isup2.hkl

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

supplementary crystallographic information

Comment

Thiophene derivatives possess electroluminescence (Bugatti et al., 2006) and biological properties (Brault et al., 2005) effects. As part of our studies in this area, we report here the synthesis and crystal structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1. The dihedral angles between the thiophene ring and its pendant O3- and O4-containing oxadiazole rings are 1.2 (3)° and 9.8 (3)°, respectively. Some short intramolecular C—H···O contacts occur (Table 1), which might help to stabilise the molecular conformation.

Experimental

3,4-Dibutoxythiophene-2,5-dicarbohydrazide (10 mmol) was dissolved in pyridine (30 ml), and benzoyl chloride (22 mmol) was dropped into the mixture, which was heated to 348 K for 12 h. After cooling, the mixture was poured into cold water to recover a white solid.

The white solid was dissolved in phosphoryl trichloride (30 ml). The mixture was refluxed for 12 h. After cooling, the mixture was poured onto crushed ice. The crude title compound was purified by recrystalization from trichloromethane. Yield is 82% and melting point is 439 K. Yellow blocks of (I) were obtained by slow evaporation of an ethyl acetate solution.

Refinement

All the H atoms were placed geometrically (C—H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level. The dashed lines indicate short C—H···O contacts.

Crystal data

C28H28N4O4SF000 = 1088
Mr = 516.60Dx = 1.302 Mg m3
Monoclinic, P21/cMelting point: 421 K
Hall symbol: -P 2ybcMo Kα radiation λ = 0.71073 Å
a = 7.6770 (15) ÅCell parameters from 25 reflections
b = 16.871 (3) Åθ = 8–12º
c = 20.398 (4) ŵ = 0.16 mm1
β = 93.77 (3)ºT = 293 (2) K
V = 2636.2 (9) Å3Block, yellow
Z = 40.30 × 0.10 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.026
Radiation source: fine-focus sealed tubeθmax = 25.2º
Monochromator: graphiteθmin = 1.6º
T = 293(2) Kh = −9→9
ω/2θ scansk = 0→20
Absorption correction: ψ scan(North et al., 1968)l = 0→24
Tmin = 0.953, Tmax = 0.9923 standard reflections
5100 measured reflections every 200 reflections
4722 independent reflections intensity decay: none
1918 reflections with I > 2σ(I)

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.087H-atom parameters constrained
wR(F2) = 0.203  w = 1/[σ2(Fo2) + (0.05P)2 + 1.9P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4722 reflectionsΔρmax = 0.21 e Å3
328 parametersΔρmin = −0.19 e Å3
216 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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.

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

xyzUiso*/Ueq
S0.33758 (19)−0.11570 (10)0.45424 (7)0.0779 (5)
O10.1262 (5)0.0185 (3)0.57876 (19)0.0886 (13)
O20.1425 (5)−0.1444 (3)0.6260 (2)0.1014 (14)
O30.2220 (4)0.1120 (2)0.46996 (16)0.0660 (9)
O40.2964 (4)−0.2925 (2)0.58119 (17)0.0745 (10)
N10.3116 (6)0.1309 (3)0.3736 (2)0.0812 (13)
N20.3341 (6)0.0491 (3)0.3892 (2)0.0889 (14)
N30.3550 (7)−0.2952 (3)0.4784 (2)0.0961 (16)
N40.3787 (7)−0.3714 (3)0.5034 (3)0.1047 (17)
C10.3901 (9)0.1927 (4)0.6908 (3)0.117 (2)
H1B0.45300.21450.72890.176*
H1C0.35840.23460.66050.176*
H1D0.46250.15500.67020.176*
C20.2296 (10)0.1526 (4)0.7109 (4)0.123 (2)
H2A0.26390.11350.74420.147*
H2B0.15800.19170.73130.147*
C30.1260 (9)0.1145 (4)0.6610 (3)0.103 (2)
H3B0.08970.15410.62840.124*
H3C0.02130.09550.68010.124*
C40.2018 (10)0.0482 (4)0.6267 (4)0.124 (3)
H4A0.31490.06550.61360.148*
H4B0.22340.00620.65870.148*
C50.1109 (8)−0.0976 (4)0.8310 (3)0.110 (2)
H5A0.0177−0.06230.84060.165*
H5B0.2190−0.06880.83260.165*
H5C0.1189−0.13940.86290.165*
C60.0773 (10)−0.1303 (5)0.7676 (4)0.133 (3)
H6A0.0710−0.08470.73860.160*
H6B−0.0411−0.15030.76770.160*
C70.1689 (10)−0.1895 (4)0.7319 (3)0.121 (3)
H7A0.2515−0.21680.76200.145*
H7B0.0858−0.22820.71370.145*
C80.2609 (9)−0.1551 (4)0.6795 (3)0.0933 (19)
H8A0.3113−0.10460.69330.112*
H8B0.3544−0.18990.66790.112*
C90.1390 (10)0.4056 (5)0.4462 (4)0.121 (2)
H9A0.11990.45960.45120.146*
C100.2049 (9)0.3780 (4)0.3906 (3)0.106 (2)
H10A0.22780.41430.35790.127*
C110.2395 (8)0.3001 (4)0.3801 (3)0.0958 (19)
H11A0.28250.28330.34090.115*
C120.2091 (6)0.2467 (4)0.4291 (3)0.0761 (15)
C130.1422 (8)0.2760 (4)0.4859 (3)0.0948 (19)
H13A0.12410.24100.52000.114*
C140.1013 (9)0.3556 (5)0.4938 (4)0.112 (2)
H14A0.04940.37330.53100.134*
C150.2477 (6)0.1639 (4)0.4222 (3)0.0686 (14)
C160.2767 (6)0.0429 (4)0.4483 (3)0.0697 (14)
C170.2698 (6)−0.0266 (3)0.4849 (3)0.070
C180.1997 (7)−0.0394 (4)0.5486 (3)0.0780 (15)
C190.2193 (7)−0.1189 (4)0.5687 (3)0.0821 (16)
C200.2853 (7)−0.1688 (4)0.5252 (3)0.0726 (14)
C210.3116 (7)−0.2500 (4)0.5263 (3)0.0748 (15)
C220.3433 (7)−0.3675 (4)0.5646 (3)0.0733 (15)
C230.3445 (6)−0.4282 (4)0.6127 (3)0.0758 (15)
C240.3920 (8)−0.5050 (4)0.5971 (3)0.0933 (18)
H24A0.4189−0.51530.55410.112*
C250.4019 (8)−0.5676 (4)0.6419 (3)0.106 (2)
H25A0.4390−0.61780.63010.127*
C260.3544 (8)−0.5514 (4)0.7040 (3)0.099 (2)
H26A0.3560−0.59210.73480.119*
C270.3070 (8)−0.4807 (5)0.7213 (3)0.0974 (19)
H27A0.2774−0.47250.76420.117*
C280.2985 (8)−0.4146 (4)0.6764 (3)0.0991 (19)
H28A0.2635−0.36460.68960.119*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S0.0735 (9)0.0961 (11)0.0650 (8)0.0052 (9)0.0125 (7)−0.0064 (9)
O10.079 (3)0.127 (4)0.063 (2)0.007 (3)0.025 (2)−0.022 (3)
O20.096 (3)0.123 (4)0.088 (3)−0.002 (3)0.025 (3)0.004 (3)
O30.055 (2)0.078 (2)0.066 (2)0.0061 (19)0.0101 (16)0.005 (2)
O40.073 (2)0.080 (3)0.071 (2)0.004 (2)0.0025 (18)−0.003 (2)
N10.067 (3)0.107 (4)0.070 (3)0.011 (3)0.004 (2)0.008 (3)
N20.081 (3)0.113 (4)0.074 (3)0.020 (3)0.011 (2)−0.009 (3)
N30.104 (4)0.097 (4)0.088 (3)0.016 (3)0.016 (3)0.011 (3)
N40.122 (4)0.103 (4)0.093 (3)0.013 (3)0.036 (3)−0.010 (3)
C10.120 (6)0.126 (6)0.107 (5)−0.018 (5)0.014 (4)−0.015 (5)
C20.140 (7)0.112 (6)0.117 (6)−0.013 (5)0.010 (5)−0.011 (5)
C30.105 (5)0.103 (5)0.102 (5)0.003 (4)0.010 (4)−0.020 (5)
C40.134 (7)0.107 (6)0.127 (7)0.011 (5)−0.019 (5)−0.012 (5)
C50.096 (5)0.122 (6)0.112 (5)0.004 (4)0.008 (4)−0.019 (5)
C60.145 (7)0.129 (7)0.128 (7)0.001 (6)0.028 (6)−0.002 (6)
C70.149 (7)0.128 (7)0.087 (5)0.006 (6)0.010 (5)0.010 (5)
C80.110 (5)0.094 (5)0.076 (4)−0.012 (4)0.007 (4)0.003 (4)
C90.132 (6)0.105 (5)0.127 (5)0.021 (4)0.002 (5)−0.011 (4)
C100.121 (5)0.097 (4)0.099 (4)−0.008 (4)0.003 (4)0.013 (4)
C110.100 (4)0.088 (4)0.103 (4)0.001 (4)0.027 (4)0.007 (4)
C120.049 (3)0.102 (4)0.076 (4)−0.014 (3)0.000 (3)−0.008 (3)
C130.096 (4)0.107 (4)0.082 (4)−0.015 (4)0.014 (3)−0.018 (4)
C140.112 (5)0.118 (5)0.105 (5)0.005 (4)0.010 (4)−0.028 (4)
C150.056 (3)0.087 (4)0.063 (3)−0.009 (3)0.014 (3)−0.009 (3)
C160.053 (3)0.087 (4)0.070 (3)0.001 (3)0.012 (3)0.006 (3)
C170.0700.0700.0700.0000.0050.000
C180.068 (4)0.086 (4)0.079 (4)−0.015 (3)0.001 (3)0.005 (3)
C190.072 (3)0.110 (4)0.067 (3)−0.004 (3)0.026 (3)0.002 (3)
C200.067 (3)0.089 (4)0.062 (3)0.005 (3)0.006 (3)0.005 (3)
C210.062 (3)0.093 (4)0.069 (4)0.006 (3)0.002 (3)0.000 (3)
C220.057 (3)0.081 (4)0.082 (4)0.012 (3)0.004 (3)−0.006 (3)
C230.052 (3)0.095 (4)0.082 (4)0.002 (3)0.016 (3)−0.001 (3)
C240.093 (4)0.101 (4)0.085 (4)0.006 (4)−0.002 (3)−0.002 (3)
C250.103 (5)0.100 (4)0.117 (5)−0.001 (4)0.026 (4)0.005 (4)
C260.085 (4)0.113 (5)0.098 (4)−0.003 (4)−0.005 (3)0.021 (4)
C270.086 (4)0.129 (5)0.078 (4)−0.011 (4)0.012 (3)0.010 (4)
C280.100 (4)0.102 (4)0.096 (4)−0.003 (4)0.018 (4)−0.003 (4)

Geometric parameters (Å, °)

S—C171.722 (5)C7—C81.442 (7)
S—C201.771 (5)C7—H7A0.9700
O1—C41.212 (7)C7—H7B0.9700
O1—C181.302 (6)C8—H8A0.9700
O2—C81.385 (6)C8—H8B0.9700
O2—C191.410 (6)C9—C141.331 (8)
O3—C161.325 (6)C9—C101.355 (8)
O3—C151.334 (6)C9—H9A0.9300
O4—C211.341 (6)C10—C111.361 (8)
O4—C221.365 (6)C10—H10A0.9300
N1—C151.264 (6)C11—C121.376 (7)
N1—N21.423 (6)C11—H11A0.9300
N2—C161.315 (6)C12—C131.389 (7)
N3—C211.300 (7)C12—C151.437 (8)
N3—N41.390 (6)C13—C141.391 (8)
N4—C221.296 (6)C13—H13A0.9300
C1—C21.487 (8)C14—H14A0.9300
C1—H1B0.9600C16—C171.392 (7)
C1—H1C0.9600C17—C181.455 (7)
C1—H1D0.9600C18—C191.408 (8)
C2—C31.406 (8)C19—C201.346 (7)
C2—H2A0.9700C20—C211.385 (7)
C2—H2B0.9700C22—C231.418 (7)
C3—C41.461 (8)C23—C281.387 (7)
C3—H3B0.9700C23—C241.390 (7)
C3—H3C0.9700C24—C251.395 (8)
C4—H4A0.9700C24—H24A0.9300
C4—H4B0.9700C25—C261.370 (8)
C5—C61.414 (8)C25—H25A0.9300
C5—H5A0.9600C26—C271.303 (8)
C5—H5B0.9600C26—H26A0.9300
C5—H5C0.9600C27—C281.442 (8)
C6—C71.445 (8)C27—H27A0.9300
C6—H6A0.9700C28—H28A0.9300
C6—H6B0.9700
C17—S—C2093.1 (3)C10—C9—H9A119.8
C4—O1—C18119.5 (6)C9—C10—C11123.3 (7)
C8—O2—C19113.8 (5)C9—C10—H10A118.3
C16—O3—C15105.6 (4)C11—C10—H10A118.3
C21—O4—C22104.5 (5)C10—C11—C12118.3 (7)
C15—N1—N2107.5 (5)C10—C11—H11A120.8
C16—N2—N1103.8 (5)C12—C11—H11A120.8
C21—N3—N4107.5 (5)C11—C12—C13117.6 (6)
C22—N4—N3106.0 (5)C11—C12—C15121.3 (6)
C2—C1—H1B109.5C13—C12—C15121.1 (6)
C2—C1—H1C109.5C12—C13—C14122.5 (7)
H1B—C1—H1C109.5C12—C13—H13A118.7
C2—C1—H1D109.5C14—C13—H13A118.7
H1B—C1—H1D109.5C9—C14—C13117.8 (7)
H1C—C1—H1D109.5C9—C14—H14A121.1
C3—C2—C1116.7 (6)C13—C14—H14A121.1
C3—C2—H2A108.1N1—C15—O3111.5 (5)
C1—C2—H2A108.1N1—C15—C12126.8 (6)
C3—C2—H2B108.1O3—C15—C12121.7 (5)
C1—C2—H2B108.1N2—C16—O3111.6 (5)
H2A—C2—H2B107.3N2—C16—C17125.9 (6)
C2—C3—C4118.2 (7)O3—C16—C17122.5 (5)
C2—C3—H3B107.8C16—C17—C18129.3 (5)
C4—C3—H3B107.8C16—C17—S121.1 (4)
C2—C3—H3C107.8C18—C17—S109.4 (4)
C4—C3—H3C107.8O1—C18—C19128.2 (5)
H3B—C3—H3C107.1O1—C18—C17120.5 (5)
O1—C4—C3121.2 (7)C19—C18—C17111.3 (6)
O1—C4—H4A107.0C20—C19—C18116.2 (5)
C3—C4—H4A107.0C20—C19—O2123.5 (6)
O1—C4—H4B107.0C18—C19—O2119.3 (5)
C3—C4—H4B107.0C19—C20—C21132.0 (6)
H4A—C4—H4B106.8C19—C20—S109.8 (5)
C6—C5—H5A109.5C21—C20—S118.2 (5)
C6—C5—H5B109.5N3—C21—O4110.7 (6)
H5A—C5—H5B109.5N3—C21—C20127.8 (6)
C6—C5—H5C109.5O4—C21—C20121.5 (6)
H5A—C5—H5C109.5N4—C22—O4111.2 (6)
H5B—C5—H5C109.5N4—C22—C23129.6 (6)
C5—C6—C7131.6 (7)O4—C22—C23119.1 (5)
C5—C6—H6A104.3C28—C23—C24117.1 (6)
C7—C6—H6A104.3C28—C23—C22122.6 (6)
C5—C6—H6B104.3C24—C23—C22120.3 (6)
C7—C6—H6B104.3C23—C24—C25124.1 (6)
H6A—C6—H6B105.6C23—C24—H24A118.0
C8—C7—C6111.9 (7)C25—C24—H24A118.0
C8—C7—H7A109.2C26—C25—C24116.7 (7)
C6—C7—H7A109.2C26—C25—H25A121.7
C8—C7—H7B109.2C24—C25—H25A121.7
C6—C7—H7B109.2C27—C26—C25121.9 (7)
H7A—C7—H7B107.9C27—C26—H26A119.1
O2—C8—C7108.0 (6)C25—C26—H26A119.1
O2—C8—H8A110.1C26—C27—C28122.6 (7)
C7—C8—H8A110.1C26—C27—H27A118.7
O2—C8—H8B110.1C28—C27—H27A118.7
C7—C8—H8B110.1C23—C28—C27117.6 (6)
H8A—C8—H8B108.4C23—C28—H28A121.2
C14—C9—C10120.3 (8)C27—C28—H28A121.2
C14—C9—H9A119.8
C15—N1—N2—C160.4 (6)C16—C17—C18—C19−179.6 (5)
C21—N3—N4—C221.7 (7)S—C17—C18—C194.3 (6)
C1—C2—C3—C463.0 (10)O1—C18—C19—C20173.6 (5)
C18—O1—C4—C3178.5 (6)C17—C18—C19—C20−4.5 (7)
C2—C3—C4—O1−172.1 (7)O1—C18—C19—O24.8 (9)
C5—C6—C7—C8−107.2 (9)C17—C18—C19—O2−173.3 (5)
C19—O2—C8—C7−173.6 (6)C8—O2—C19—C2087.0 (7)
C6—C7—C8—O2−81.9 (7)C8—O2—C19—C18−105.1 (6)
C14—C9—C10—C11−1.2 (12)C18—C19—C20—C21−175.3 (6)
C9—C10—C11—C12−1.3 (11)O2—C19—C20—C21−7.0 (10)
C10—C11—C12—C131.0 (9)C18—C19—C20—S2.5 (7)
C10—C11—C12—C15−178.0 (6)O2—C19—C20—S170.8 (4)
C11—C12—C13—C141.9 (9)C17—S—C20—C190.2 (4)
C15—C12—C13—C14−179.1 (6)C17—S—C20—C21178.3 (5)
C10—C9—C14—C134.0 (11)N4—N3—C21—O4−3.1 (7)
C12—C13—C14—C9−4.4 (10)N4—N3—C21—C20175.8 (5)
N2—N1—C15—O3−0.7 (6)C22—O4—C21—N33.2 (6)
N2—N1—C15—C12177.7 (5)C22—O4—C21—C20−175.8 (5)
C16—O3—C15—N10.7 (6)C19—C20—C21—N3170.1 (6)
C16—O3—C15—C12−177.7 (5)S—C20—C21—N3−7.5 (8)
C11—C12—C15—N10.4 (9)C19—C20—C21—O4−11.1 (10)
C13—C12—C15—N1−178.6 (5)S—C20—C21—O4171.3 (4)
C11—C12—C15—O3178.6 (5)N3—N4—C22—O40.3 (7)
C13—C12—C15—O3−0.4 (8)N3—N4—C22—C23179.2 (5)
N1—N2—C16—O30.1 (6)C21—O4—C22—N4−2.1 (6)
N1—N2—C16—C17179.2 (5)C21—O4—C22—C23178.9 (5)
C15—O3—C16—N2−0.4 (6)N4—C22—C23—C28−178.3 (6)
C15—O3—C16—C17−179.6 (5)O4—C22—C23—C280.5 (8)
N2—C16—C17—C18−176.2 (5)N4—C22—C23—C241.3 (9)
O3—C16—C17—C182.9 (9)O4—C22—C23—C24−179.9 (5)
N2—C16—C17—S−0.5 (8)C28—C23—C24—C25−2.4 (9)
O3—C16—C17—S178.5 (4)C22—C23—C24—C25178.0 (6)
C20—S—C17—C16−179.0 (5)C23—C24—C25—C262.7 (10)
C20—S—C17—C18−2.6 (4)C24—C25—C26—C27−1.9 (10)
C4—O1—C18—C1974.6 (9)C25—C26—C27—C280.9 (11)
C4—O1—C18—C17−107.4 (7)C24—C23—C28—C271.1 (8)
C16—C17—C18—O12.1 (9)C22—C23—C28—C27−179.2 (5)
S—C17—C18—O1−174.0 (4)C26—C27—C28—C23−0.5 (10)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6A···O20.972.602.973 (9)103
C8—H8B···O40.972.493.089 (7)120
C13—H13A···O30.932.542.857 (8)100

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2756).

References

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