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Acta Cryst. (2008). E64, o2154    [ doi:10.1107/S1600536808033953 ]

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

J. Guan, H. Li, L. Han and H. Wang

Abstract top

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.

Comment top

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.

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXS97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level.
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 top
Crystal data top
C36H44N4O4SF(000) = 1344
Mr = 628.81Dx = 1.190 Mg m−3
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 mm−1
β = 94.24 (3)°T = 293 K
V = 3510.3 (12) Å3Block, yellow
Z = 40.20 × 0.10 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		2847 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 top
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 = 1.06 w = 1/[σ2(Fo2) + (0.03P)2 + 3P]
where P = (Fo2 + 2Fc2)/3
6295 reflections(Δ/σ)max < 0.001
391 parametersΔρmax = 0.17 e Å−3
138 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C36H44N4O4SV = 3510.3 (12) Å3
Mr = 628.81Z = 4
Monoclinic, P21/cMo Kα radiation
a = 19.421 (4) ŵ = 0.14 mm−1
b = 17.387 (4) ÅT = 293 K
c = 10.424 (2) Å0.20 × 0.10 × 0.10 mm
β = 94.24 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		2847 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.032
Tmin = 0.974, Tmax = 0.987θmax = 25.2°
6675 measured reflections3 standard reflections every 200 reflections
6295 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.085H-atom parameters constrained
wR(F2) = 0.164Δρmax = 0.17 e Å−3
S = 1.06Δρmin = −0.21 e Å−3
6295 reflectionsAbsolute structure: ?
391 parametersFlack parameter: ?
138 restraintsRogers parameter: ?
Special details top

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) top
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) top
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, °) top
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, °) top
D—H···AD—HH···AD···AD—H···A
C36—H36B···O20.972.503.149 (6)124
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C36—H36B···O20.972.503.149 (6)124
references
References top

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.

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.