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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o622.
Published online 2009 February 28. doi:  10.1107/S1600536809006539
PMCID: PMC2968503

2-{3,4-Dibut­oxy-5-[5-(3-methyl­phen­yl)-1,3,4-oxadiazol-2-yl]thio­phen-2-yl}-5-(3-methyl­phen­yl)-1,3,4-oxadiazole

Abstract

In the title compound, C30H32N4O4S, the dihedral angles between the central thio­phene ring and the pendant oxadiazole rings are 10.1 (2) and 6.8 (3)°. The dihedral angles between each oxadiazole ring and its adjacent benzene ring are 6.8 (2) and 5.3 (3)°.

Related literature

For background on the applications of thio­phenes, see: Laurent et al. (2005 [triangle]).

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Object name is e-65-0o622-scheme1.jpg

Experimental

Crystal data

  • C30H32N4O4S
  • M r = 544.67
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o622-efi1.jpg
  • a = 16.421 (3) Å
  • b = 14.432 (3) Å
  • c = 12.338 (3) Å
  • β = 98.36 (3)°
  • V = 2892.9 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.15 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.956, T max = 0.985
  • 5526 measured reflections
  • 5260 independent reflections
  • 2161 reflections with I > 2σ(I)
  • R int = 0.048
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.071
  • wR(F 2) = 0.167
  • S = 1.00
  • 5260 reflections
  • 352 parameters
  • 52 restraints
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.13 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006539/hb2914sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006539/hb2914Isup2.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). The molecular structure of (I) is shown in Fig. 1.

Experimental

3,4-Dibutoxythiophene-2,5-dicarbohydrazide (10 mmol) was dissolved in pyridine (30 ml), and 4-methylbenzoyl chloride (22 mmol) was dropped into the mixture. The resulting mixture was reaction at 348 K for 5 h. After cooling, the mixture was poured into cold water. After filtrating and drying, a white solid compound was obtained.

The crude compound was dissolved in phosphoryl trichloride (30 ml). 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 78% and melting point is 440 K. Light yellow blocks of (I) were obtained by slow evaporation of 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. Short H···O contacts are shown as dashed lines.

Crystal data

C30H32N4O4SF(000) = 1152
Mr = 544.67Dx = 1.251 Mg m3
Monoclinic, P21/cMelting point: 440 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 16.421 (3) ÅCell parameters from 25 reflections
b = 14.432 (3) Åθ = 8–12°
c = 12.338 (3) ŵ = 0.15 mm1
β = 98.36 (3)°T = 293 K
V = 2892.9 (11) Å3Block, light yellow
Z = 40.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer2161 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
graphiteθmax = 25.3°, θmin = 1.3°
ω/2θ scansh = 0→19
Absorption correction: ψ scan (North et al., 1968)k = 0→17
Tmin = 0.956, Tmax = 0.985l = −14→14
5526 measured reflections3 standard reflections every 200 reflections
5260 independent reflections intensity decay: 1%

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)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.04P)2 + 1.2P] where P = (Fo2 + 2Fc2)/3
5260 reflections(Δ/σ)max < 0.001
352 parametersΔρmax = 0.14 e Å3
52 restraintsΔρmin = −0.13 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
S0.26175 (7)0.22411 (9)0.70173 (9)0.0957 (4)
N10.4127 (2)0.2826 (3)1.0254 (3)0.1009 (12)
O10.36204 (17)0.4067 (2)0.9317 (3)0.1033 (10)
C10.5391 (3)0.4136 (3)1.4095 (3)0.1134 (16)
H1B0.55660.46221.46070.170*
H1C0.58540.37511.40040.170*
H1D0.49770.37681.43660.170*
O20.28937 (19)0.4885 (3)0.7289 (2)0.1031 (10)
N20.3700 (2)0.2498 (3)0.9236 (3)0.1017 (12)
C20.5029 (3)0.4566 (4)1.2971 (4)0.0997 (15)
O30.1942 (2)0.4382 (2)0.5174 (2)0.1087 (10)
N30.1668 (3)0.1439 (4)0.4892 (3)0.1150 (14)
C30.5001 (3)0.5472 (5)1.2837 (4)0.1192 (18)
H3B0.52190.58451.34230.143*
O40.12985 (18)0.2718 (2)0.4131 (3)0.1015 (9)
C40.4659 (3)0.5907 (4)1.1849 (4)0.1109 (16)
H4A0.46440.65431.17220.133*
N40.1195 (3)0.1222 (3)0.3878 (4)0.1079 (13)
C50.4329 (3)0.5193 (5)1.1053 (5)0.122 (2)
H5A0.40600.54211.03910.147*
C60.4354 (3)0.4324 (5)1.1124 (4)0.1071 (17)
C70.4737 (3)0.4002 (4)1.2129 (4)0.1107 (16)
H7A0.47960.33661.22280.133*
C80.4034 (3)0.3681 (5)1.0312 (4)0.1074 (16)
C90.3451 (3)0.3246 (4)0.8750 (4)0.1014 (15)
C100.2980 (3)0.3296 (4)0.7657 (4)0.0948 (13)
C110.2710 (3)0.4006 (4)0.7014 (4)0.0964 (13)
C120.2256 (3)0.5477 (4)0.7441 (4)0.1291 (18)
H12A0.20300.53110.80990.155*
H12B0.18200.54450.68210.155*
C130.2629 (3)0.6454 (4)0.7548 (5)0.1299 (19)
H13A0.30860.65040.71340.156*
H13B0.22190.69150.72810.156*
C140.2906 (3)0.6583 (4)0.8693 (5)0.133 (2)
H14A0.33250.61140.88820.160*
H14B0.24440.63980.90540.160*
C150.3226 (3)0.7401 (4)0.9256 (4)0.1344 (19)
H15A0.33660.72691.00240.202*
H15B0.28180.78820.91560.202*
H15C0.37090.76020.89670.202*
C160.2334 (3)0.3697 (4)0.5944 (4)0.1108 (16)
C170.2452 (3)0.4653 (4)0.4567 (4)0.1100 (15)
H17A0.27660.41220.43780.132*
H17B0.28340.50800.49800.132*
C180.2077 (3)0.5116 (4)0.3538 (4)0.1224 (17)
H18A0.16480.47090.31840.147*
H18B0.18070.56720.37450.147*
C190.2573 (3)0.5376 (4)0.2730 (4)0.1191 (17)
H19A0.28800.48420.25340.143*
H19B0.29640.58470.30270.143*
C200.2018 (4)0.5762 (4)0.1680 (5)0.161 (2)
H20A0.23580.59200.11370.242*
H20B0.17320.63050.18710.242*
H20C0.16260.52980.13930.242*
C210.2166 (3)0.2781 (4)0.5906 (3)0.0928 (12)
C220.1734 (3)0.2329 (4)0.4973 (4)0.0921 (13)
C230.0989 (3)0.1984 (5)0.3461 (5)0.1063 (16)
C240.0474 (3)0.2255 (6)0.2409 (5)0.1150 (17)
C250.0259 (3)0.3153 (5)0.2097 (5)0.1220 (19)
H25A0.04380.36330.25770.146*
C26−0.0201 (3)0.3368 (4)0.1127 (6)0.1280 (19)
H26A−0.03360.39800.09480.154*
C27−0.0465 (4)0.2655 (6)0.0408 (5)0.130 (2)
H27A−0.07880.2768−0.02630.156*
C28−0.0232 (4)0.1798 (6)0.0728 (5)0.126 (2)
C290.0204 (3)0.1594 (4)0.1728 (5)0.1141 (17)
H29A0.03100.09790.19260.137*
C30−0.0652 (4)0.1206 (4)−0.0041 (5)0.150 (2)
H30A−0.07510.06450.03350.225*
H30B−0.02900.1080−0.05680.225*
H30C−0.11640.1446−0.04090.225*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S0.0992 (8)0.0908 (9)0.0966 (8)−0.0007 (7)0.0129 (6)0.0017 (7)
N10.094 (3)0.108 (3)0.098 (3)0.001 (3)0.006 (2)−0.003 (3)
O10.100 (2)0.117 (3)0.090 (2)0.0008 (19)0.0034 (16)0.002 (2)
C10.130 (4)0.115 (4)0.093 (3)−0.009 (3)0.014 (3)−0.019 (3)
O20.099 (2)0.106 (3)0.106 (2)0.014 (2)0.0213 (16)−0.011 (2)
N20.096 (3)0.111 (4)0.094 (3)0.017 (2)0.001 (2)−0.004 (2)
C20.099 (3)0.113 (4)0.085 (3)−0.011 (3)0.007 (2)−0.011 (3)
O30.123 (2)0.107 (3)0.097 (2)0.000 (2)0.0192 (18)0.020 (2)
N30.129 (4)0.115 (4)0.099 (3)0.005 (3)0.010 (2)0.013 (3)
C30.140 (4)0.122 (5)0.089 (3)−0.032 (4)−0.007 (3)−0.022 (3)
O40.095 (2)0.108 (3)0.101 (2)0.004 (2)0.0117 (16)0.006 (2)
C40.098 (3)0.121 (5)0.115 (4)−0.014 (3)0.023 (3)−0.017 (4)
N40.107 (3)0.117 (4)0.099 (3)−0.004 (3)0.014 (2)−0.016 (3)
C50.097 (4)0.149 (6)0.116 (4)0.007 (4)−0.004 (3)−0.010 (5)
C60.112 (4)0.131 (5)0.079 (3)0.000 (4)0.014 (3)−0.001 (4)
C70.097 (3)0.118 (5)0.118 (4)−0.008 (3)0.020 (3)−0.003 (4)
C80.100 (4)0.131 (5)0.091 (3)0.006 (4)0.013 (3)0.005 (4)
C90.101 (3)0.115 (5)0.086 (3)−0.011 (3)0.002 (2)−0.008 (3)
C100.099 (3)0.098 (4)0.085 (3)−0.001 (3)0.006 (2)0.008 (3)
C110.100 (3)0.096 (4)0.097 (3)−0.005 (3)0.029 (3)−0.010 (3)
C120.117 (4)0.122 (5)0.145 (4)0.005 (4)0.007 (3)−0.014 (4)
C130.136 (5)0.124 (5)0.135 (5)0.018 (4)0.036 (4)0.026 (4)
C140.126 (4)0.142 (5)0.132 (4)0.013 (4)0.020 (3)0.000 (4)
C150.138 (4)0.146 (5)0.126 (4)0.026 (4)0.041 (3)0.022 (4)
C160.145 (5)0.090 (4)0.093 (3)0.002 (4)0.004 (3)0.007 (3)
C170.122 (4)0.100 (4)0.109 (3)−0.001 (3)0.017 (3)0.009 (3)
C180.146 (4)0.098 (4)0.128 (4)0.001 (3)0.036 (3)−0.005 (3)
C190.142 (5)0.092 (4)0.128 (4)−0.005 (3)0.035 (4)−0.021 (3)
C200.192 (6)0.118 (5)0.169 (6)−0.007 (4)0.010 (5)0.037 (4)
C210.102 (3)0.094 (3)0.080 (3)0.010 (3)0.005 (2)0.008 (3)
C220.083 (3)0.102 (4)0.090 (3)0.002 (3)0.009 (2)0.009 (3)
C230.107 (4)0.107 (5)0.105 (4)−0.014 (4)0.015 (3)−0.010 (4)
C240.098 (4)0.144 (6)0.104 (4)−0.010 (4)0.015 (3)0.001 (4)
C250.106 (4)0.142 (6)0.118 (4)−0.001 (4)0.016 (3)−0.021 (4)
C260.113 (4)0.118 (5)0.154 (5)−0.006 (4)0.023 (4)0.004 (5)
C270.117 (4)0.148 (6)0.125 (5)−0.013 (5)0.020 (4)−0.006 (5)
C280.115 (5)0.150 (7)0.115 (5)−0.010 (5)0.021 (4)−0.018 (5)
C290.102 (4)0.123 (5)0.115 (4)−0.010 (3)0.008 (3)−0.011 (4)
C300.142 (5)0.169 (6)0.143 (5)−0.009 (5)0.035 (4)0.007 (5)

Geometric parameters (Å, °)

S—C211.655 (4)C13—H13A0.9700
S—C101.777 (5)C13—H13B0.9700
N1—C81.246 (6)C14—C151.432 (6)
N1—N21.427 (5)C14—H14A0.9700
O1—C91.384 (5)C14—H14B0.9700
O1—C81.427 (5)C15—H15A0.9600
C1—C21.556 (6)C15—H15B0.9600
C1—H1B0.9600C15—H15C0.9600
C1—H1C0.9600C16—C211.350 (6)
C1—H1D0.9600C17—C181.486 (6)
O2—C111.337 (5)C17—H17A0.9700
O2—C121.385 (5)C17—H17B0.9700
N2—C91.274 (6)C18—C191.426 (6)
C2—C31.318 (6)C18—H18A0.9700
C2—C71.352 (6)C18—H18B0.9700
O3—C171.264 (4)C19—C201.574 (6)
O3—C161.456 (5)C19—H19A0.9700
N3—C221.292 (5)C19—H19B0.9700
N3—N41.409 (5)C20—H20A0.9600
C3—C41.413 (6)C20—H20B0.9600
C3—H3B0.9300C20—H20C0.9600
O4—C221.300 (5)C21—C221.420 (6)
O4—C231.394 (6)C23—C241.496 (7)
C4—C51.472 (7)C24—C291.306 (7)
C4—H4A0.9300C24—C251.383 (7)
N4—C231.240 (6)C25—C261.355 (7)
C5—C61.257 (7)C25—H25A0.9300
C5—H5A0.9300C26—C271.386 (7)
C6—C71.387 (6)C26—H26A0.9300
C6—C81.410 (7)C27—C281.338 (8)
C7—H7A0.9300C27—H27A0.9300
C9—C101.456 (6)C28—C291.366 (7)
C10—C111.332 (6)C28—C301.383 (7)
C11—C161.444 (6)C29—H29A0.9300
C12—C131.536 (6)C30—H30A0.9600
C12—H12A0.9700C30—H30B0.9600
C12—H12B0.9700C30—H30C0.9600
C13—C141.431 (6)
C21—S—C1092.6 (3)H15A—C15—H15B109.5
C8—N1—N2109.3 (5)C14—C15—H15C109.5
C9—O1—C897.8 (4)H15A—C15—H15C109.5
C2—C1—H1B109.5H15B—C15—H15C109.5
C2—C1—H1C109.5C21—C16—C11113.1 (5)
H1B—C1—H1C109.5C21—C16—O3125.0 (5)
C2—C1—H1D109.5C11—C16—O3118.5 (5)
H1B—C1—H1D109.5O3—C17—C18114.7 (4)
H1C—C1—H1D109.5O3—C17—H17A108.6
C11—O2—C12118.1 (4)C18—C17—H17A108.6
C9—N2—N1102.5 (4)O3—C17—H17B108.6
C3—C2—C7119.9 (5)C18—C17—H17B108.6
C3—C2—C1120.7 (5)H17A—C17—H17B107.6
C7—C2—C1119.4 (5)C19—C18—C17120.5 (5)
C17—O3—C16109.2 (4)C19—C18—H18A107.2
C22—N3—N4108.6 (4)C17—C18—H18A107.2
C2—C3—C4123.5 (5)C19—C18—H18B107.2
C2—C3—H3B118.3C17—C18—H18B107.2
C4—C3—H3B118.3H18A—C18—H18B106.8
C22—O4—C23104.8 (4)C18—C19—C20110.3 (5)
C3—C4—C5109.0 (5)C18—C19—H19A109.6
C3—C4—H4A125.5C20—C19—H19A109.6
C5—C4—H4A125.5C18—C19—H19B109.6
C23—N4—N3104.7 (5)C20—C19—H19B109.6
C6—C5—C4130.3 (6)H19A—C19—H19B108.1
C6—C5—H5A114.8C19—C20—H20A109.5
C4—C5—H5A114.8C19—C20—H20B109.5
C5—C6—C7113.7 (6)H20A—C20—H20B109.5
C5—C6—C8127.1 (6)C19—C20—H20C109.5
C7—C6—C8119.2 (6)H20A—C20—H20C109.5
C2—C7—C6123.4 (6)H20B—C20—H20C109.5
C2—C7—H7A118.3C16—C21—C22123.6 (5)
C6—C7—H7A118.3C16—C21—S111.6 (4)
N1—C8—C6131.1 (6)C22—C21—S124.5 (4)
N1—C8—O1112.6 (5)N3—C22—O4109.7 (5)
C6—C8—O1115.8 (6)N3—C22—C21123.1 (5)
N2—C9—O1117.4 (4)O4—C22—C21127.0 (5)
N2—C9—C10124.7 (5)N4—C23—O4112.0 (5)
O1—C9—C10117.9 (5)N4—C23—C24132.7 (6)
C11—C10—C9132.5 (5)O4—C23—C24115.3 (6)
C11—C10—S109.5 (4)C29—C24—C25117.2 (6)
C9—C10—S117.9 (4)C29—C24—C23117.6 (7)
C10—C11—O2122.4 (5)C25—C24—C23125.2 (6)
C10—C11—C16111.6 (5)C26—C25—C24123.1 (6)
O2—C11—C16125.2 (5)C26—C25—H25A118.4
O2—C12—C13106.1 (5)C24—C25—H25A118.4
O2—C12—H12A110.5C25—C26—C27118.6 (7)
C13—C12—H12A110.5C25—C26—H26A120.7
O2—C12—H12B110.5C27—C26—H26A120.7
C13—C12—H12B110.5C28—C27—C26116.6 (7)
H12A—C12—H12B108.7C28—C27—H27A121.7
C14—C13—C12105.6 (5)C26—C27—H27A121.7
C14—C13—H13A110.6C27—C28—C29123.7 (7)
C12—C13—H13A110.6C27—C28—C30106.0 (7)
C14—C13—H13B110.6C29—C28—C30129.1 (8)
C12—C13—H13B110.6C24—C29—C28120.5 (7)
H13A—C13—H13B108.7C24—C29—H29A119.7
C13—C14—C15128.9 (6)C28—C29—H29A119.7
C13—C14—H14A105.1C28—C30—H30A107.0
C15—C14—H14A105.1C28—C30—H30B106.6
C13—C14—H14B105.1H30A—C30—H30B109.5
C15—C14—H14B105.1C28—C30—H30C114.7
H14A—C14—H14B105.9H30A—C30—H30C109.5
C14—C15—H15A109.5H30B—C30—H30C109.5
C14—C15—H15B109.5
C8—N1—N2—C95.5 (6)O2—C11—C16—C21−176.0 (4)
C7—C2—C3—C41.6 (9)C10—C11—C16—O3174.7 (4)
C1—C2—C3—C4−178.1 (4)O2—C11—C16—O3−15.8 (7)
C2—C3—C4—C51.9 (7)C17—O3—C16—C21−108.3 (6)
C22—N3—N4—C23−2.9 (6)C17—O3—C16—C1194.0 (5)
C3—C4—C5—C6−3.9 (9)C16—O3—C17—C18161.7 (4)
C4—C5—C6—C71.8 (10)O3—C17—C18—C19−174.0 (5)
C4—C5—C6—C8−178.8 (5)C17—C18—C19—C20174.6 (4)
C3—C2—C7—C6−4.2 (8)C11—C16—C21—C22174.4 (4)
C1—C2—C7—C6175.5 (4)O3—C16—C21—C2215.8 (8)
C5—C6—C7—C22.5 (8)C11—C16—C21—S−12.2 (6)
C8—C6—C7—C2−177.0 (5)O3—C16—C21—S−170.9 (4)
N2—N1—C8—C6−177.4 (5)C10—S—C21—C165.6 (4)
N2—N1—C8—O1−6.6 (6)C10—S—C21—C22178.9 (4)
C5—C6—C8—N1168.7 (6)N4—N3—C22—O44.3 (5)
C7—C6—C8—N1−11.9 (9)N4—N3—C22—C21179.2 (4)
C5—C6—C8—O1−1.8 (9)C23—O4—C22—N3−3.9 (5)
C7—C6—C8—O1177.6 (4)C23—O4—C22—C21−178.5 (4)
C9—O1—C8—N14.7 (5)C16—C21—C22—N3170.8 (5)
C9—O1—C8—C6177.0 (4)S—C21—C22—N3−1.6 (7)
N1—N2—C9—O1−2.5 (6)C16—C21—C22—O4−15.3 (8)
N1—N2—C9—C10179.4 (4)S—C21—C22—O4172.3 (3)
C8—O1—C9—N2−0.9 (5)N3—N4—C23—O40.4 (6)
C8—O1—C9—C10177.2 (4)N3—N4—C23—C24−178.7 (5)
N2—C9—C10—C11−176.1 (5)C22—O4—C23—N42.1 (6)
O1—C9—C10—C115.9 (8)C22—O4—C23—C24−178.6 (4)
N2—C9—C10—S8.1 (7)N4—C23—C24—C29−4.4 (9)
O1—C9—C10—S−169.9 (3)O4—C23—C24—C29176.6 (4)
C21—S—C10—C112.7 (4)N4—C23—C24—C25175.6 (6)
C21—S—C10—C9179.4 (4)O4—C23—C24—C25−3.4 (8)
C9—C10—C11—O24.4 (8)C29—C24—C25—C26−0.9 (8)
S—C10—C11—O2−179.6 (3)C23—C24—C25—C26179.1 (5)
C9—C10—C11—C16174.3 (5)C24—C25—C26—C27−0.4 (8)
S—C10—C11—C16−9.7 (5)C25—C26—C27—C28−0.9 (8)
C12—O2—C11—C10−116.6 (5)C26—C27—C28—C293.6 (9)
C12—O2—C11—C1674.9 (6)C26—C27—C28—C30172.3 (5)
C11—O2—C12—C13−170.5 (4)C25—C24—C29—C283.5 (8)
O2—C12—C13—C14−90.1 (5)C23—C24—C29—C28−176.5 (5)
C12—C13—C14—C15−173.2 (6)C27—C28—C29—C24−5.2 (9)
C10—C11—C16—C2114.5 (6)C30—C28—C29—C24−171.1 (6)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2914).

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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