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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2154.
Published online 2008 October 22. doi:  10.1107/S1600536808033953
PMCID: PMC2959615

2-(4-tert-Butyl­phen­yl)-5-{3,4-dibutoxy-5-[5-(4-tert-butyl­phen­yl)-1,3,4-oxadiazol-2-yl]-2-thienyl}-1,3,4-oxadiazole

Abstract

In the title compound, C36H44N4O4S, the dihedral angles between the central thio­phene ring and the pendent oxadiazole rings are 12.7 (2) and 13.7 (2)°, and the dihedral angles between the oxadiazole rings and their adjacent benzene rings are 6.1 (2) and 17.5 (2)°. An intra­molecular C—H(...)O inter­action may help to establish the conformation.

Related literature

For background, see: Laurent et al. (2005 [triangle]).

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Object name is e-64-o2154-scheme1.jpg

Experimental

Crystal data

  • C36H44N4O4S
  • M r = 628.81
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2154-efi1.jpg
  • a = 19.421 (4) Å
  • b = 17.387 (4) Å
  • c = 10.424 (2) Å
  • β = 94.24 (3)°
  • V = 3510.3 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.14 mm−1
  • T = 293 (2) K
  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.974, T max = 0.987
  • 6675 measured reflections
  • 6295 independent reflections
  • 2847 reflections with I > 2σ(I)
  • R int = 0.032
  • 3 standard reflections every 200 reflections intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.085
  • wR(F 2) = 0.164
  • S = 1.06
  • 6295 reflections
  • 391 parameters
  • 138 restraints
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.21 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: SHELXS97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033953/hb2818sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033953/hb2818Isup2.hkl

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

supplementary crystallographic information

Comment

Some thiophene derivatives possess biological properties (Laurent et al., 2005). As part of our studies in this area, we report here the synthesis and crystal structure of the title compound, (I).

An intramolecular C—H···O hydrogen bond (Table 1) may help to establish the molecular conformation of (I). The molecular structure of (I) is shown in Fig. 1 and relevant dihedral angles are given in the Abstract.

Experimental

3,4-Dibutoxythiophene-2,5-dicarbohydrazide (10 mmol) was dissolved in pyridine (30 ml) and 4-tert-butylbenzoyl chloride (22 mmol) was added dropwise to the mixture. The resulting mixture was heated to 342 K for 12 h. After cooling, the mixture was poured onto ice water and a white solid was obtained.

The crude compound was dissolved in phosphoryl trichloride (30 ml) and the mixture was refluxed for 12 h. After cooling, the mixture was poured onto crushed ice. The title compound was obtained and purified by recrystalization from trichloromethane. Yield is 85% and melting point is 421 K. Yellow blocks of (I) suitable were obtained by slow evaporation of an ethyl acetate solution.

Refinement

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

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level.

Crystal data

C36H44N4O4SF(000) = 1344
Mr = 628.81Dx = 1.190 Mg m3
Monoclinic, P21/cMelting point: 421 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 19.421 (4) ÅCell parameters from 25 reflections
b = 17.387 (4) Åθ = 9–12°
c = 10.424 (2) ŵ = 0.14 mm1
β = 94.24 (3)°T = 293 K
V = 3510.3 (12) Å3Block, yellow
Z = 40.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer2847 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
graphiteθmax = 25.2°, θmin = 1.1°
ω/2θ scansh = −23→23
Absorption correction: ψ scan (North et al., 1968)k = 0→20
Tmin = 0.974, Tmax = 0.987l = 0→12
6675 measured reflections3 standard reflections every 200 reflections
6295 independent reflections intensity decay: none

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.085Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.03P)2 + 3P] where P = (Fo2 + 2Fc2)/3
6295 reflections(Δ/σ)max < 0.001
391 parametersΔρmax = 0.17 e Å3
138 restraintsΔρmin = −0.21 e Å3

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
S0.21507 (6)0.13771 (7)0.42321 (11)0.0737 (4)
O10.10436 (14)0.25970 (16)0.6562 (2)0.0669 (8)
O20.36725 (13)0.19395 (15)0.2071 (2)0.0642 (8)
O30.21365 (18)0.3469 (2)0.5488 (3)0.0970 (11)
O40.32043 (16)0.32198 (19)0.3699 (3)0.0894 (10)
N10.1172 (2)0.1352 (2)0.6394 (4)0.0923 (12)
N20.0679 (2)0.1487 (2)0.7245 (4)0.0867 (12)
N30.3300 (2)0.0804 (2)0.2671 (4)0.0836 (12)
N40.3820 (2)0.0680 (2)0.1858 (4)0.0888 (13)
C1−0.15814 (18)0.3412 (2)1.1340 (4)0.1110 (19)
H1B−0.19260.37031.17430.167*
H1C−0.12220.32651.19740.167*
H1D−0.17880.29591.09510.167*
C2−0.18704 (18)0.4193 (2)0.9408 (4)0.122 (2)
H2B−0.21950.44610.98980.183*
H2C−0.20960.37660.89700.183*
H2D−0.16960.45380.87890.183*
C3−0.0929 (2)0.4586 (3)1.0956 (5)0.1034 (18)
H3B−0.12630.48761.13890.155*
H3C−0.07330.49051.03260.155*
H3D−0.05710.44121.15710.155*
C4−0.1275 (2)0.3906 (3)1.0304 (5)0.0951 (17)
C5−0.0756 (2)0.3445 (3)0.9573 (4)0.0738 (13)
C6−0.0359 (2)0.3824 (3)0.8756 (4)0.0907 (15)
H6A−0.03870.43570.86840.109*
C70.0083 (2)0.3422 (3)0.8037 (4)0.0863 (14)
H7A0.03390.36940.74690.104*
C80.0163 (2)0.2667 (3)0.8112 (4)0.0670 (12)
C9−0.0241 (2)0.2255 (3)0.8991 (4)0.0895 (15)
H9A−0.02110.17240.90710.107*
C10−0.0676 (3)0.2678 (3)0.9712 (4)0.0862 (14)
H10A−0.09220.24241.03150.103*
C110.0613 (2)0.2196 (3)0.7351 (4)0.0669 (12)
C120.1359 (2)0.1992 (3)0.5977 (4)0.0680 (12)
C130.6959 (3)0.1763 (3)−0.0922 (5)0.1127 (19)
H13A0.73340.1850−0.14540.169*
H13B0.69590.1233−0.06590.169*
H13C0.70130.2087−0.01760.169*
C140.62126 (18)0.1443 (2)−0.2875 (3)0.1019 (17)
H14A0.65890.1547−0.33970.153*
H14B0.57830.1550−0.33590.153*
H14C0.62240.0912−0.26230.153*
C150.63464 (18)0.2763 (2)−0.2131 (3)0.1153 (19)
H15A0.67260.2798−0.26680.173*
H15B0.64290.3095−0.14010.173*
H15C0.59280.2916−0.26130.173*
C160.6278 (2)0.1950 (3)−0.1681 (4)0.0737 (13)
C170.5690 (2)0.1827 (3)−0.0836 (4)0.0673 (12)
C180.5604 (2)0.1117 (3)−0.0274 (4)0.0725 (13)
H18A0.59140.0725−0.04220.087*
C190.5093 (2)0.0977 (3)0.0467 (4)0.0779 (13)
H19A0.50570.04930.08340.093*
C200.4595 (2)0.1557 (3)0.0719 (4)0.0649 (11)
C210.4679 (2)0.2243 (3)0.0192 (4)0.0732 (13)
H21A0.43710.26350.03570.088*
C220.5210 (2)0.2397 (3)−0.0600 (4)0.0735 (12)
H22A0.52440.2880−0.09720.088*
C230.4030 (2)0.1344 (3)0.1547 (4)0.0662 (12)
C240.3240 (2)0.1546 (3)0.2765 (4)0.0656 (12)
C250.2752 (2)0.1947 (3)0.3536 (4)0.0642 (11)
C260.2736 (2)0.2678 (3)0.3940 (4)0.0637 (11)
C270.2228 (2)0.2800 (3)0.4822 (4)0.0711 (13)
C280.1870 (2)0.2153 (3)0.5084 (4)0.0668 (12)
C290.1698 (4)0.5589 (4)0.4059 (7)0.163 (3)
H29A0.14910.60060.35660.245*
H29B0.17630.51590.35020.245*
H29C0.21370.57490.44540.245*
C300.1233 (4)0.5356 (4)0.5085 (7)0.153 (3)
H30A0.11630.57620.57000.184*
H30B0.07930.51510.47400.184*
C310.1722 (3)0.4753 (3)0.5594 (6)0.123 (2)
H31A0.21540.50130.58390.148*
H31B0.15470.45660.63830.148*
C320.1891 (3)0.4099 (4)0.4886 (6)0.129 (2)
H32A0.14790.39500.43640.155*
H32B0.22290.42580.42980.155*
C330.4367 (3)0.5060 (4)0.1190 (6)0.146 (2)
H33A0.44710.51400.03140.218*
H33B0.47740.48880.16860.218*
H33C0.42110.55340.15410.218*
C340.3837 (3)0.4491 (4)0.1234 (6)0.137 (2)
H34A0.39640.40570.07150.165*
H34B0.34150.47050.08260.165*
C350.3683 (3)0.4197 (3)0.2492 (5)0.1124 (19)
H35A0.35650.46340.30110.135*
H35B0.41070.39810.28930.135*
C360.3132 (3)0.3612 (3)0.2580 (5)0.1072 (18)
H36A0.26850.38650.25100.129*
H36B0.31460.32540.18680.129*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S0.0887 (8)0.0642 (7)0.0711 (7)−0.0006 (7)0.0253 (6)−0.0056 (7)
O10.0741 (18)0.0740 (19)0.0540 (16)0.0001 (15)0.0148 (14)−0.0039 (15)
O20.0681 (17)0.0533 (17)0.0740 (19)0.0009 (15)0.0247 (15)−0.0071 (15)
O30.130 (3)0.079 (3)0.083 (2)0.008 (2)0.021 (2)−0.028 (2)
O40.097 (2)0.082 (2)0.092 (2)−0.028 (2)0.017 (2)−0.004 (2)
N10.126 (3)0.066 (3)0.088 (3)0.006 (2)0.033 (2)−0.008 (2)
N20.118 (3)0.063 (2)0.082 (3)0.000 (2)0.033 (2)−0.012 (2)
N30.094 (3)0.070 (3)0.089 (3)−0.006 (2)0.024 (2)−0.005 (2)
N40.120 (3)0.056 (3)0.098 (3)0.001 (2)0.056 (3)0.001 (2)
C10.108 (4)0.121 (5)0.110 (4)0.015 (4)0.045 (3)−0.007 (4)
C20.100 (4)0.136 (5)0.127 (5)0.019 (4)−0.010 (4)−0.001 (4)
C30.084 (3)0.098 (4)0.133 (5)0.003 (3)0.038 (3)−0.037 (4)
C40.062 (3)0.105 (4)0.124 (4)0.023 (3)0.046 (3)−0.004 (4)
C50.082 (3)0.071 (3)0.070 (3)−0.010 (3)0.018 (2)−0.005 (3)
C60.102 (4)0.079 (3)0.095 (3)0.000 (3)0.031 (3)−0.005 (3)
C70.090 (3)0.088 (3)0.082 (3)0.006 (3)0.021 (3)0.004 (3)
C80.072 (3)0.070 (3)0.062 (3)0.001 (2)0.020 (2)−0.016 (2)
C90.112 (4)0.081 (3)0.082 (3)0.014 (3)0.045 (3)0.003 (3)
C100.114 (4)0.071 (3)0.077 (3)−0.012 (3)0.032 (3)0.001 (3)
C110.068 (3)0.077 (3)0.056 (3)0.005 (2)0.010 (2)0.002 (2)
C120.077 (3)0.074 (3)0.054 (3)0.011 (3)0.011 (2)0.001 (2)
C130.094 (4)0.140 (5)0.105 (4)0.006 (4)0.016 (3)0.009 (4)
C140.120 (4)0.108 (4)0.083 (4)0.004 (3)0.041 (3)−0.008 (3)
C150.109 (4)0.117 (5)0.121 (5)−0.010 (4)0.011 (4)0.003 (4)
C160.083 (3)0.083 (3)0.056 (3)−0.001 (3)0.014 (2)−0.002 (3)
C170.066 (3)0.076 (3)0.060 (3)0.001 (2)0.007 (2)−0.008 (2)
C180.080 (3)0.068 (3)0.070 (3)0.018 (2)0.009 (2)−0.001 (2)
C190.094 (3)0.073 (3)0.067 (3)0.018 (3)0.006 (3)−0.001 (2)
C200.067 (3)0.066 (3)0.062 (3)0.008 (2)0.000 (2)−0.010 (2)
C210.086 (3)0.057 (3)0.077 (3)0.011 (2)0.009 (2)−0.015 (2)
C220.075 (3)0.067 (3)0.078 (3)0.006 (2)0.007 (2)−0.005 (2)
C230.079 (3)0.061 (3)0.059 (3)0.020 (3)0.011 (2)−0.003 (3)
C240.056 (3)0.079 (3)0.062 (3)0.005 (2)0.008 (2)−0.008 (3)
C250.061 (3)0.074 (3)0.059 (3)0.002 (2)0.012 (2)−0.011 (2)
C260.070 (3)0.060 (3)0.060 (3)−0.003 (2)0.001 (2)−0.005 (2)
C270.080 (3)0.061 (3)0.073 (3)0.005 (3)0.014 (3)−0.015 (3)
C280.071 (3)0.084 (3)0.047 (2)0.004 (3)0.020 (2)−0.012 (2)
C290.181 (7)0.152 (7)0.153 (7)0.007 (6)−0.013 (6)0.002 (5)
C300.171 (7)0.133 (6)0.159 (7)0.013 (6)0.029 (6)−0.011 (5)
C310.160 (6)0.084 (4)0.126 (5)0.014 (4)0.016 (5)0.006 (4)
C320.138 (6)0.119 (6)0.127 (6)0.032 (5)−0.015 (4)0.000 (5)
C330.147 (6)0.143 (6)0.149 (6)−0.011 (5)0.023 (5)0.027 (5)
C340.128 (6)0.140 (6)0.143 (6)−0.023 (5)−0.002 (5)0.009 (5)
C350.095 (4)0.119 (5)0.123 (5)−0.027 (4)0.008 (4)0.029 (4)
C360.106 (4)0.105 (4)0.111 (5)0.003 (4)0.006 (4)0.024 (4)

Geometric parameters (Å, °)

S—C281.726 (4)C14—H14B0.9600
S—C251.732 (4)C14—H14C0.9600
O1—C121.382 (5)C15—C161.499 (5)
O1—C111.402 (4)C15—H15A0.9600
O2—C241.336 (4)C15—H15B0.9600
O2—C231.380 (4)C15—H15C0.9600
O3—C321.334 (6)C16—C171.507 (5)
O3—C271.374 (5)C17—C181.383 (5)
O4—C261.345 (5)C17—C221.394 (5)
O4—C361.349 (5)C18—C191.324 (5)
N1—C121.259 (5)C18—H18A0.9300
N1—N21.372 (5)C19—C201.434 (5)
N2—C111.245 (5)C19—H19A0.9300
N3—C241.300 (5)C20—C211.329 (5)
N3—N41.383 (4)C20—C231.493 (5)
N4—C231.275 (5)C21—C221.394 (5)
C1—C41.533 (6)C21—H21A0.9300
C1—H1B0.9600C22—H22A0.9300
C1—H1C0.9600C24—C251.464 (5)
C1—H1D0.9600C25—C261.340 (5)
C2—C41.517 (6)C26—C271.414 (5)
C2—H2B0.9600C27—C281.359 (5)
C2—H2C0.9599C29—C301.506 (8)
C2—H2D0.9600C29—H29A0.9600
C3—C41.497 (6)C29—H29B0.9600
C3—H3B0.9600C29—H29C0.9600
C3—H3C0.9600C30—C311.487 (8)
C3—H3D0.9600C30—H30A0.9700
C4—C51.533 (6)C30—H30B0.9700
C5—C101.350 (6)C31—C321.407 (6)
C5—C61.361 (5)C31—H31A0.9700
C6—C71.371 (6)C31—H31B0.9700
C6—H6A0.9300C32—H32A0.9700
C7—C81.324 (5)C32—H32B0.9700
C7—H7A0.9300C33—C341.432 (7)
C8—C91.440 (5)C33—H33A0.9600
C8—C111.471 (5)C33—H33B0.9600
C9—C101.382 (5)C33—H33C0.9600
C9—H9A0.9300C34—C351.458 (7)
C10—H10A0.9300C34—H34A0.9700
C12—C281.438 (5)C34—H34B0.9700
C13—C161.526 (6)C35—C361.485 (6)
C13—H13A0.9600C35—H35A0.9700
C13—H13B0.9600C35—H35B0.9700
C13—H13C0.9600C36—H36A0.9700
C14—C161.523 (5)C36—H36B0.9700
C14—H14A0.9600
C28—S—C2590.9 (2)C22—C17—C16123.2 (4)
C12—O1—C11100.6 (3)C19—C18—C17122.0 (4)
C24—O2—C23100.6 (3)C19—C18—H18A119.0
C32—O3—C27120.9 (4)C17—C18—H18A119.0
C26—O4—C36119.1 (4)C18—C19—C20121.5 (4)
C12—N1—N2107.8 (4)C18—C19—H19A119.2
C11—N2—N1108.0 (4)C20—C19—H19A119.2
C24—N3—N4105.9 (3)C21—C20—C19116.8 (4)
C23—N4—N3106.0 (3)C21—C20—C23125.3 (4)
C4—C1—H1B109.5C19—C20—C23117.8 (4)
C4—C1—H1C109.5C20—C21—C22122.3 (4)
H1B—C1—H1C109.5C20—C21—H21A118.9
C4—C1—H1D109.5C22—C21—H21A118.9
H1B—C1—H1D109.5C17—C22—C21120.2 (4)
H1C—C1—H1D109.5C17—C22—H22A119.9
C4—C2—H2B109.5C21—C22—H22A119.9
C4—C2—H2C109.8N4—C23—O2113.6 (4)
H2B—C2—H2C109.5N4—C23—C20129.3 (4)
C4—C2—H2D109.2O2—C23—C20117.1 (4)
H2B—C2—H2D109.5N3—C24—O2113.8 (3)
H2C—C2—H2D109.5N3—C24—C25125.4 (4)
C4—C3—H3B109.5O2—C24—C25120.8 (4)
C4—C3—H3C109.5C26—C25—C24131.0 (4)
H3B—C3—H3C109.5C26—C25—S112.2 (3)
C4—C3—H3D109.5C24—C25—S116.2 (3)
H3B—C3—H3D109.5C25—C26—O4124.9 (4)
H3C—C3—H3D109.5C25—C26—C27112.3 (4)
C3—C4—C2108.3 (4)O4—C26—C27122.1 (4)
C3—C4—C5110.4 (4)C28—C27—O3120.8 (4)
C2—C4—C5111.4 (4)C28—C27—C26113.5 (4)
C3—C4—C1107.9 (4)O3—C27—C26125.3 (4)
C2—C4—C1107.5 (3)C27—C28—C12132.8 (4)
C5—C4—C1111.2 (4)C27—C28—S111.0 (3)
C10—C5—C6118.6 (4)C12—C28—S116.1 (3)
C10—C5—C4122.5 (4)C30—C29—H29A109.5
C6—C5—C4118.8 (4)C30—C29—H29B109.5
C5—C6—C7120.1 (5)H29A—C29—H29B109.5
C5—C6—H6A120.0C30—C29—H29C109.5
C7—C6—H6A120.0H29A—C29—H29C109.5
C8—C7—C6123.3 (5)H29B—C29—H29C109.5
C8—C7—H7A118.3C31—C30—C2992.4 (6)
C6—C7—H7A118.3C31—C30—H30A113.2
C7—C8—C9117.6 (4)C29—C30—H30A113.2
C7—C8—C11126.3 (4)C31—C30—H30B113.2
C9—C8—C11116.1 (4)C29—C30—H30B113.2
C10—C9—C8117.7 (4)H30A—C30—H30B110.6
C10—C9—H9A121.1C32—C31—C30123.4 (6)
C8—C9—H9A121.1C32—C31—H31A106.5
C5—C10—C9122.5 (4)C30—C31—H31A106.5
C5—C10—H10A118.7C32—C31—H31B106.5
C9—C10—H10A118.7C30—C31—H31B106.5
N2—C11—O1111.8 (4)H31A—C31—H31B106.5
N2—C11—C8131.9 (4)O3—C32—C31120.4 (6)
O1—C11—C8116.3 (4)O3—C32—H32A107.2
N1—C12—O1111.8 (4)C31—C32—H32A107.2
N1—C12—C28128.9 (4)O3—C32—H32B107.2
O1—C12—C28119.1 (4)C31—C32—H32B107.2
C16—C13—H13A109.5H32A—C32—H32B106.9
C16—C13—H13B109.5C34—C33—H33A109.5
H13A—C13—H13B109.5C34—C33—H33B109.5
C16—C13—H13C109.5H33A—C33—H33B109.5
H13A—C13—H13C109.5C34—C33—H33C109.5
H13B—C13—H13C109.5H33A—C33—H33C109.5
C16—C14—H14A109.5H33B—C33—H33C109.5
C16—C14—H14B109.5C33—C34—C35117.8 (6)
H14A—C14—H14B109.5C33—C34—H34A107.9
C16—C14—H14C109.5C35—C34—H34A107.9
H14A—C14—H14C109.5C33—C34—H34B107.9
H14B—C14—H14C109.5C35—C34—H34B107.9
C16—C15—H15A109.5H34A—C34—H34B107.2
C16—C15—H15B109.5C34—C35—C36119.5 (5)
H15A—C15—H15B109.5C34—C35—H35A107.5
C16—C15—H15C109.5C36—C35—H35A107.5
H15A—C15—H15C109.5C34—C35—H35B107.5
H15B—C15—H15C109.5C36—C35—H35B107.5
C15—C16—C17113.9 (4)H35A—C35—H35B107.0
C15—C16—C14107.1 (3)O4—C36—C35111.7 (5)
C17—C16—C14112.1 (4)O4—C36—H36A109.3
C15—C16—C13105.6 (4)C35—C36—H36A109.3
C17—C16—C13109.4 (4)O4—C36—H36B109.3
C14—C16—C13108.5 (4)C35—C36—H36B109.3
C18—C17—C22117.1 (4)H36A—C36—H36B107.9
C18—C17—C16119.6 (4)
C28—S—C25—C24172.5 (3)C9—C8—C11—N26.1 (7)
C28—S—C25—C260.4 (3)C8—C9—C10—C53.3 (7)
C25—S—C28—C12−175.5 (3)N1—C12—C28—S13.7 (6)
C25—S—C28—C270.1 (3)O1—C12—C28—S−171.4 (3)
C12—O1—C11—N20.8 (4)N1—C12—C28—C27−160.6 (5)
C12—O1—C11—C8−177.9 (3)O1—C12—C28—C2714.3 (7)
C11—O1—C12—N1−2.8 (4)C13—C16—C17—C18−57.0 (6)
C11—O1—C12—C28−178.6 (4)C13—C16—C17—C22124.3 (5)
C24—O2—C23—N41.9 (5)C14—C16—C17—C1863.2 (5)
C24—O2—C23—C20−177.8 (4)C14—C16—C17—C22−115.5 (5)
C23—O2—C24—N3−1.5 (4)C15—C16—C17—C18−174.9 (4)
C23—O2—C24—C25178.9 (4)C15—C16—C17—C226.5 (6)
C32—O3—C27—C2670.3 (6)C22—C17—C18—C19−0.6 (6)
C32—O3—C27—C28−117.5 (5)C16—C17—C22—C21179.8 (4)
C27—O3—C32—C31172.5 (5)C16—C17—C18—C19−179.3 (4)
C36—O4—C26—C2584.4 (6)C18—C17—C22—C211.2 (6)
C36—O4—C26—C27−105.3 (5)C17—C18—C19—C200.5 (7)
C26—O4—C36—C35178.6 (4)C18—C19—C20—C21−1.0 (6)
N2—N1—C12—O13.8 (5)C18—C19—C20—C23178.9 (4)
N2—N1—C12—C28179.0 (4)C23—C20—C21—C22−178.3 (4)
C12—N1—N2—C11−3.2 (5)C19—C20—C23—O2162.7 (4)
N1—N2—C11—O11.4 (5)C19—C20—C23—N4−16.9 (7)
N1—N2—C11—C8179.7 (4)C21—C20—C23—O2−17.4 (6)
C24—N3—N4—C230.6 (5)C19—C20—C21—C221.7 (6)
N4—N3—C24—O20.7 (5)C21—C20—C23—N4163.0 (5)
N4—N3—C24—C25−179.7 (4)C20—C21—C22—C17−1.8 (7)
N3—N4—C23—C20178.1 (4)O2—C24—C25—S172.4 (3)
N3—N4—C23—O2−1.6 (5)N3—C24—C25—S−7.1 (6)
C1—C4—C5—C6−170.1 (4)N3—C24—C25—C26163.2 (5)
C3—C4—C5—C10129.2 (5)O2—C24—C25—C26−17.2 (7)
C3—C4—C5—C6−50.5 (6)S—C25—C26—O4170.4 (3)
C2—C4—C5—C10−110.3 (5)C24—C25—C26—C27−171.4 (4)
C1—C4—C5—C109.5 (6)S—C25—C26—C27−0.7 (5)
C2—C4—C5—C670.0 (5)C24—C25—C26—O4−0.2 (8)
C10—C5—C6—C73.9 (7)O4—C26—C27—C28−170.7 (4)
C4—C5—C10—C9175.7 (4)C25—C26—C27—O3173.5 (4)
C6—C5—C10—C9−4.7 (7)C25—C26—C27—C280.8 (5)
C4—C5—C6—C7−176.5 (4)O4—C26—C27—O32.0 (7)
C5—C6—C7—C8−1.9 (7)O3—C27—C28—S−173.5 (3)
C6—C7—C8—C90.5 (6)O3—C27—C28—C121.0 (7)
C6—C7—C8—C11178.3 (4)C26—C27—C28—S−0.5 (5)
C9—C8—C11—O1−175.6 (3)C26—C27—C28—C12174.1 (4)
C7—C8—C11—O16.6 (6)C29—C30—C31—C32−64.9 (7)
C7—C8—C11—N2−171.8 (5)C30—C31—C32—O3−157.7 (6)
C7—C8—C9—C10−1.1 (6)C33—C34—C35—C36179.3 (5)
C11—C8—C9—C10−179.2 (4)C34—C35—C36—O4159.5 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C36—H36B···O20.972.503.149 (6)124

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2818).

References

  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • Laurent, B., Evelyne, M. & Adrien, N. (2005). Eur. J. Med. Chem.40, 757–763. [PubMed]
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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