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Acta Cryst. (2009). E65, o622    [ doi:10.1107/S1600536809006539 ]

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

L.-N. Han, R.-Z. Lu, M. Zhang and H. Wang

Abstract top

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)°.

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). The molecular structure of (I) is shown in Fig. 1.

Related literature top

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

Experimental top

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 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: SHELXL97 (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. Short H···O contacts are shown as dashed lines.
2-{3,4-Dibutoxy-5-[5-(3-methylphenyl)-1,3,4-oxadiazol-2-yl]thiophen-2-yl}- 5-(3-methylphenyl)-1,3,4-oxadiazole top
Crystal data top
C30H32N4O4SF(000) = 1152
Mr = 544.67Dx = 1.251 Mg m−3
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 mm−1
β = 98.36 (3)°T = 293 K
V = 2892.9 (11) Å3Block, light yellow
Z = 40.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		2161 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 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)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-atom parameters constrained
S = 1.00 w = 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 Å−3
52 restraintsΔρmin = −0.13 e Å−3
Crystal data top
C30H32N4O4SV = 2892.9 (11) Å3
Mr = 544.67Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.421 (3) ŵ = 0.15 mm−1
b = 14.432 (3) ÅT = 293 K
c = 12.338 (3) Å0.30 × 0.20 × 0.10 mm
β = 98.36 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		2161 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.048
Tmin = 0.956, Tmax = 0.985θmax = 25.3°
5526 measured reflections3 standard reflections every 200 reflections
5260 independent reflections intensity decay: 1%
Refinement top
R[F2 > 2σ(F2)] = 0.071H-atom parameters constrained
wR(F2) = 0.167Δρmax = 0.14 e Å−3
S = 1.00Δρmin = −0.13 e Å−3
5260 reflectionsAbsolute structure: ?
352 parametersFlack parameter: ?
52 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
S0.26175 (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) top
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, °) top
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)
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.