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Acta Cryst. (2008). E64, o2298    [ doi:10.1107/S1600536808035848 ]

2-(4-Chlorophenyl)-5-{3,4-dibutoxy-5-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]thiophen-2-yl}-1,3,4-oxadiazole

H.-L. Li, H.-W. Wang, R.-Z. Lu and H.-B. Wang

Abstract top

In the title compound, C28H26Cl2N4O4S, the dihedral angles between the two chlorophenyl rings and the two oxadiazol rings are 10.51 (4)° and 13.55 (3)°, respectively. The thiophene ring is oriented at dihedral angles of 5.59 (4)°, 8.33 (4)° and 4.41 (4)°, 11.05 (3)°, respectively, with respect to the two oxadiazol and the two chlorophenyl rings. The intramolecular C-H...O hydrogen bond results in the formation of a five-membered ring. In the crystal structure, [pi]-[pi] contacts between the oxadiazol rings, the chlorophenyl rings and the chlorophenyl and oxadiazol rings [centroid-centroid distances = 3.428 (3) Å, 3.750 (3) Å and 3.768 (3) Å, respectively] are present.

Comment top

Thiophene derivatives possess electroluminescence (Blumstengel et al., 1999; Bugatti et al., 2006) and biological (Laurent et al., 2005) properties. As part of our studies in this area, we report herein the synthesis and crystal structure of the title compound.

In the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C9-C14), B (N1/N2/O3/C15/C16), C (S/C17-C20), D (N3/N4/O4/C21/C22) and E (C23-C28) are, of course, planar and the dihedral angles between them are A/B = 7.54 (3)°, A/C = 4.41 (4)°, A/D = 6.88 (4)°, A/E = 10.51 (4)°, B/C = 5.59 (4)°, B/D = 13.55 (3)°, B/E = 16.57 (3)°, C/D = 8.33 (4)°, C/E = 11.05 (3)° and D/E = 3.78 (3)°. The intramolecular C-H···O hydrogen bonds (Table 1) result in the formation of three five- and one six-membered rings F (O3/C12/C13/C15/H13A), G (O1/C6-C8/H6A), H (O4/C22/C23/C28/H28A) and I (O1/O2/C4/C18/C19/H4B). Rings F and H are planar and they are oriented with respect to the adjacent rings at dihedral angles of A/F = 4.18 (4)°, B/F = 8.02 (4)°, D/I = 3.47 (4)° and E/I = 2.05 (4)°. Ring G adopts envelope conformation with C7 atom displaced by 0.570 (3) Å from the plane of the other ring atoms, while ring I has twisted conformation.

In the crystal structure, the π—π contacts between A, D and E rings, Cg3···Cg3i, Cg4···Cg4i and Cg5···Cg3ii [symmetry codes: (i) -x, y, -1/2 - z; (ii) -x, -y, -z, where Cg3, Cg4 and Cg5 are the centroids of the rings D (N3/N4/O4/C21/C22), A (C9-C14) and E (C23-C28) may stabilize the structure, with centroid-centroid distances of 3.428 (3) Å, 3.750 (3) Å and 3.768 (3) Å, respectively.

Related literature top

For general background, see: Blumstengel et al. (1999); Bugatti et al. (2006); Laurent et al. (2005). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, 3,4-dibutoxythiophene-2,5-dicarbo- hydrazide (10 mmol) was dissolved in pyridine (30 ml), and then 4-chlorobenzoyl chloride (22 mmol) was added dropwise. The resulting mixture was kept at 345 K for 12 h. After cooling, the mixture was poured into cold water. After filtration and dryness, the colorless solid compound was obtained. The crude compound dissolved in phosphoryl trichloride (30 ml). The mixture was refluxed for 12 h. After cooling, the mixture was poured into smash ice. Then, the title compound was obtained and purified by recrystalization from trichloro- methane (yield; 82.8%, m.p. 451 K). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution.

Refinement top

H atoms were positioned geometrically, with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
2-(4-Chlorophenyl)-5-{3,4-dibutoxy-5-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2- yl]thiophen-2-yl}-1,3,4-oxadiazole top
Crystal data top
C28H26Cl2N4O4SF(000) = 2432
Mr = 585.49Dx = 1.388 Mg m−3
Monoclinic, C2/cMelting point: 451K K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 19.215 (4) ÅCell parameters from 25 reflections
b = 22.847 (5) Åθ = 9–12°
c = 14.933 (3) ŵ = 0.35 mm−1
β = 121.25 (3)°T = 294 K
V = 5605 (3) Å3Block, yellow
Z = 80.30 × 0.10 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		2050 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.066
graphiteθmax = 25.2°, θmin = 1.5°
ω/2θ scansh = −22→19
Absorption correction: ψ scan
(North et al., 1968)		k = 0→27
Tmin = 0.903, Tmax = 0.966l = 0→17
10353 measured reflections3 standard reflections every 120 min
5053 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)] = 0.080Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.060P)2 + 7.P]
where P = (Fo2 + 2Fc2)/3
5053 reflections(Δ/σ)max < 0.001
298 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.46 e Å−3
Crystal data top
C28H26Cl2N4O4SV = 5605 (3) Å3
Mr = 585.49Z = 8
Monoclinic, C2/cMo Kα radiation
a = 19.215 (4) ŵ = 0.35 mm−1
b = 22.847 (5) ÅT = 294 K
c = 14.933 (3) Å0.30 × 0.10 × 0.10 mm
β = 121.25 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		2050 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.066
Tmin = 0.903, Tmax = 0.966θmax = 25.2°
10353 measured reflections3 standard reflections every 120 min
5053 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.080H-atom parameters constrained
wR(F2) = 0.198Δρmax = 0.24 e Å−3
S = 1.01Δρmin = −0.46 e Å−3
5053 reflectionsAbsolute structure: ?
298 parametersFlack parameter: ?
0 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
S0.42931 (8)0.23942 (6)0.30296 (10)0.0831 (4)
Cl10.55998 (13)−0.21791 (7)0.42942 (15)0.1331 (6)
Cl20.69885 (12)0.65697 (7)0.60696 (15)0.1313 (6)
O10.6213 (2)0.15456 (15)0.5028 (3)0.089
O20.6482 (2)0.28280 (14)0.5192 (3)0.0878 (10)
O30.49888 (19)0.07239 (14)0.3740 (2)0.077
O40.5531 (2)0.38674 (15)0.4339 (3)0.0912 (10)
N10.3730 (3)0.0474 (2)0.2575 (3)0.089
N20.3786 (3)0.1093 (2)0.2660 (3)0.0923 (12)
N30.4340 (3)0.3757 (2)0.2900 (4)0.0953 (13)
N40.4475 (3)0.4330 (2)0.3069 (4)0.0969 (13)
C10.6637 (4)0.3351 (3)0.8279 (5)0.108
H1B0.69390.33190.90280.161*
H1C0.61020.31910.80060.161*
H1D0.65920.37560.80830.161*
C20.7039 (4)0.3043 (3)0.7869 (4)0.108
H2B0.70860.26300.80440.129*
H2C0.75770.32020.81150.129*
C30.6462 (4)0.3145 (3)0.6681 (4)0.109
H3B0.59070.30340.64510.131*
H3C0.64730.35490.64900.131*
C40.6818 (3)0.2761 (3)0.6269 (4)0.100
H4A0.73980.28360.66250.120*
H4B0.67430.23600.64130.120*
C50.7651 (3)−0.0001 (3)0.6258 (4)0.1016 (17)
H5A0.7620−0.02060.67980.152*
H5B0.82070.00120.64320.152*
H5C0.7327−0.02020.56030.152*
C60.7339 (4)0.0605 (2)0.6166 (5)0.1031 (18)
H6A0.67830.05850.60110.124*
H6B0.76610.07980.68380.124*
C70.7355 (4)0.0965 (3)0.5357 (4)0.0981 (16)
H7A0.70520.07570.46970.118*
H7B0.79160.09870.55300.118*
C80.7034 (3)0.1572 (3)0.5182 (5)0.1018 (18)
H8A0.73860.18150.57830.122*
H8B0.70090.17380.45690.122*
C90.5230 (4)−0.1491 (2)0.3946 (5)0.0945 (16)
C100.4501 (4)−0.1366 (3)0.3208 (5)0.1019 (18)
H10A0.4140−0.16690.28410.122*
C110.4230 (4)−0.0771 (3)0.2937 (5)0.0971 (16)
H11A0.3714−0.06940.23670.117*
C120.4728 (3)−0.0316 (2)0.3514 (3)0.0728 (12)
C130.5496 (3)−0.0449 (2)0.4331 (4)0.089
H13A0.5834−0.01440.47340.106*
C140.5787 (4)−0.1012 (2)0.4579 (4)0.0952 (16)
H14A0.6314−0.10880.51250.114*
C150.4457 (3)0.0271 (2)0.3244 (4)0.0823 (14)
C160.4529 (3)0.1223 (2)0.3318 (4)0.0801 (13)
C170.4872 (3)0.1802 (2)0.3644 (3)0.0730 (12)
C180.5670 (3)0.1949 (2)0.4454 (3)0.0656 (11)
C190.5800 (3)0.2557 (2)0.4558 (4)0.077
C200.5068 (3)0.2866 (2)0.3816 (4)0.0741 (13)
C210.4949 (3)0.3481 (2)0.3638 (4)0.0786 (13)
C220.5193 (3)0.4405 (2)0.3924 (4)0.0817 (14)
C230.5637 (3)0.4922 (2)0.4449 (4)0.0796 (14)
C240.5285 (4)0.5466 (3)0.4006 (5)0.1096 (19)
H24A0.47710.54990.34070.132*
C250.5782 (4)0.5975 (3)0.4552 (5)0.1068 (19)
H25A0.56010.63440.42620.128*
C260.6473 (4)0.5927 (3)0.5436 (5)0.0986 (16)
C270.6769 (4)0.5396 (3)0.5885 (4)0.0925 (16)
H27A0.72510.53700.65320.111*
C280.6361 (3)0.4912 (2)0.5388 (4)0.0824 (14)
H28A0.65780.45510.56940.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0709 (8)0.0945 (9)0.0751 (8)0.0016 (7)0.0317 (7)0.0012 (7)
Cl10.1665 (17)0.0968 (11)0.1486 (15)0.0058 (11)0.0905 (14)0.0078 (10)
Cl20.1615 (17)0.1022 (12)0.1372 (14)−0.0175 (11)0.0825 (13)−0.0107 (10)
O10.082 (3)0.088 (3)0.099 (2)0.0027 (14)0.0451 (11)0.0125 (12)
O20.082 (2)0.086 (2)0.087 (2)−0.0029 (19)0.0378 (19)−0.0123 (18)
N10.082 (3)0.088 (3)0.092 (2)0.011 (2)0.036 (3)0.013 (2)
N20.070 (3)0.106 (3)0.095 (3)−0.014 (2)0.037 (3)−0.004 (2)
N30.069 (3)0.091 (3)0.106 (4)0.008 (2)0.032 (3)0.015 (3)
N40.079 (3)0.105 (4)0.096 (3)0.014 (3)0.037 (3)0.017 (3)
C10.108 (3)0.112 (3)0.101 (4)0.010 (3)0.051 (4)0.010 (4)
C20.108 (3)0.103 (3)0.096 (3)0.011 (4)0.046 (4)0.008 (3)
C30.109 (4)0.102 (3)0.099 (5)0.012 (5)0.047 (5)0.006 (4)
C40.100 (3)0.088 (4)0.110 (4)0.008 (4)0.052 (4)0.005 (3)
C50.087 (4)0.104 (4)0.099 (4)0.013 (3)0.039 (3)0.005 (3)
C60.089 (4)0.097 (4)0.105 (4)0.009 (3)0.038 (3)−0.005 (3)
C70.104 (4)0.111 (5)0.080 (4)0.008 (4)0.049 (3)0.003 (3)
C80.059 (3)0.126 (5)0.120 (4)0.016 (3)0.046 (3)0.021 (4)
C90.122 (5)0.092 (4)0.083 (4)−0.006 (4)0.063 (4)−0.009 (3)
C100.103 (5)0.099 (5)0.106 (5)−0.032 (4)0.056 (4)−0.019 (4)
C110.097 (4)0.102 (4)0.110 (4)−0.018 (4)0.066 (4)−0.012 (4)
C120.071 (3)0.092 (4)0.059 (3)−0.007 (3)0.036 (3)−0.006 (2)
C130.089 (4)0.091 (4)0.079 (2)−0.016 (4)0.036 (4)−0.004 (3)
C140.100 (4)0.090 (4)0.082 (4)−0.012 (3)0.038 (3)0.002 (3)
C150.081 (4)0.089 (4)0.087 (3)−0.024 (3)0.050 (3)−0.012 (3)
O30.077 (3)0.082 (3)0.080 (3)−0.012 (4)0.040 (3)−0.012 (3)
C160.071 (3)0.089 (4)0.079 (3)−0.004 (3)0.039 (3)−0.010 (3)
C170.066 (3)0.096 (3)0.066 (3)0.002 (3)0.040 (3)0.002 (2)
C180.058 (3)0.080 (3)0.050 (2)0.008 (2)0.021 (2)−0.011 (2)
C190.077 (3)0.097 (3)0.074 (2)−0.016 (2)0.050 (3)−0.012 (2)
C200.088 (3)0.073 (3)0.078 (3)−0.013 (3)0.056 (3)−0.010 (2)
C210.087 (4)0.090 (4)0.067 (3)−0.011 (3)0.045 (3)−0.013 (3)
O40.099 (3)0.083 (2)0.090 (2)0.010 (2)0.048 (2)0.0039 (19)
C220.089 (4)0.080 (3)0.080 (3)0.026 (3)0.047 (3)0.020 (3)
C230.082 (4)0.089 (4)0.079 (4)0.020 (3)0.050 (3)0.008 (3)
C240.111 (5)0.093 (4)0.130 (5)0.018 (4)0.067 (4)0.022 (4)
C250.132 (6)0.092 (4)0.106 (5)0.034 (4)0.068 (5)0.022 (4)
C260.088 (4)0.106 (5)0.108 (5)−0.003 (4)0.055 (4)0.002 (4)
C270.101 (4)0.096 (4)0.093 (4)0.017 (4)0.059 (3)−0.002 (3)
C280.091 (4)0.079 (3)0.084 (4)0.020 (3)0.051 (3)0.001 (3)
Geometric parameters (Å, °) top
S—C171.689 (5)C7—H7B0.9700
S—C201.716 (5)C8—H8A0.9700
Cl1—C91.693 (6)C8—H8B0.9700
Cl2—C261.748 (6)C9—C101.287 (8)
O1—C181.321 (5)C9—C141.478 (7)
O1—C81.472 (5)C10—C111.437 (8)
O2—C191.307 (5)C10—H10A0.9300
O2—C41.397 (6)C11—C121.373 (7)
N1—C151.310 (6)C11—H11A0.9300
N1—N21.419 (6)C12—C131.375 (7)
N2—C161.279 (6)C12—C151.419 (7)
N3—C211.282 (6)C13—C141.375 (7)
N3—N41.333 (6)C13—H13A0.9300
N4—C221.318 (6)C14—H14A0.9300
C1—C21.400 (7)C15—O31.369 (5)
C1—H1B0.9600O3—C161.378 (6)
C1—H1C0.9600C16—C171.445 (7)
C1—H1D0.9600C17—C181.415 (6)
C2—C31.546 (8)C18—C191.408 (6)
C2—H2B0.9700C19—C201.445 (7)
C2—H2C0.9700C20—C211.426 (7)
C3—C41.432 (7)C21—O41.381 (6)
C3—H3B0.9700O4—C221.377 (5)
C3—H3C0.9700C22—C231.429 (7)
C4—H4A0.9700C23—C281.370 (7)
C4—H4B0.9700C23—C241.407 (7)
C5—C61.486 (7)C24—C251.456 (9)
C5—H5A0.9600C24—H24A0.9300
C5—H5B0.9600C25—C261.304 (8)
C5—H5C0.9600C25—H25A0.9300
C6—C71.475 (7)C26—C271.360 (8)
C6—H6A0.9700C27—C281.337 (7)
C6—H6B0.9700C27—H27A0.9300
C7—C81.484 (7)C28—H28A0.9300
C7—H7A0.9700
C17—S—C2092.2 (2)C9—C10—H10A119.2
C18—O1—C8119.7 (4)C11—C10—H10A119.2
C19—O2—C4118.2 (4)C12—C11—C10120.6 (6)
C15—N1—N2106.5 (4)C12—C11—H11A119.7
C16—N2—N1107.6 (4)C10—C11—H11A119.7
C21—N3—N4108.6 (5)C11—C12—C13117.8 (5)
C22—N4—N3108.2 (4)C11—C12—C15120.3 (5)
C2—C1—H1B109.5C13—C12—C15121.8 (5)
C2—C1—H1C109.5C12—C13—C14123.1 (5)
H1B—C1—H1C109.5C12—C13—H13A118.5
C2—C1—H1D109.5C14—C13—H13A118.5
H1B—C1—H1D109.5C13—C14—C9117.5 (5)
H1C—C1—H1D109.5C13—C14—H14A121.3
C1—C2—C3101.3 (5)C9—C14—H14A121.3
C1—C2—H2B111.5N1—C15—O3110.2 (5)
C3—C2—H2B111.5N1—C15—C12129.8 (5)
C1—C2—H2C111.5O3—C15—C12120.0 (5)
C3—C2—H2C111.5C15—O3—C16104.8 (4)
H2B—C2—H2C109.3N2—C16—O3110.8 (5)
C4—C3—C2100.5 (5)N2—C16—C17127.1 (5)
C4—C3—H3B111.7O3—C16—C17122.1 (4)
C2—C3—H3B111.7C18—C17—C16127.4 (4)
C4—C3—H3C111.7C18—C17—S113.0 (4)
C2—C3—H3C111.7C16—C17—S119.6 (4)
H3B—C3—H3C109.4O1—C18—C19125.6 (4)
O2—C4—C3113.0 (5)O1—C18—C17122.1 (4)
O2—C4—H4A109.0C19—C18—C17112.4 (4)
C3—C4—H4A109.0O2—C19—C18127.0 (4)
O2—C4—H4B109.0O2—C19—C20122.4 (4)
C3—C4—H4B109.0C18—C19—C20110.5 (4)
H4A—C4—H4B107.8C21—C20—C19128.4 (5)
C6—C5—H5A109.5C21—C20—S119.6 (4)
C6—C5—H5B109.5C19—C20—S111.8 (4)
H5A—C5—H5B109.5N3—C21—O4110.8 (5)
C6—C5—H5C109.5N3—C21—C20129.1 (5)
H5A—C5—H5C109.5O4—C21—C20120.0 (5)
H5B—C5—H5C109.5C22—O4—C21102.8 (4)
C7—C6—C5114.6 (5)N4—C22—O4109.4 (5)
C7—C6—H6A108.6N4—C22—C23131.7 (5)
C5—C6—H6A108.6O4—C22—C23118.8 (5)
C7—C6—H6B108.6C28—C23—C24118.7 (5)
C5—C6—H6B108.6C28—C23—C22123.2 (5)
H6A—C6—H6B107.6C24—C23—C22117.9 (5)
C6—C7—C8118.8 (5)C23—C24—C25115.2 (6)
C6—C7—H7A107.6C23—C24—H24A122.4
C8—C7—H7A107.6C25—C24—H24A122.4
C6—C7—H7B107.6C26—C25—C24121.9 (6)
C8—C7—H7B107.6C26—C25—H25A119.0
H7A—C7—H7B107.0C24—C25—H25A119.0
O1—C8—C7107.7 (5)C25—C26—C27121.3 (6)
O1—C8—H8A110.2C25—C26—Cl2118.1 (5)
C7—C8—H8A110.2C27—C26—Cl2120.5 (5)
O1—C8—H8B110.2C28—C27—C26119.3 (6)
C7—C8—H8B110.2C28—C27—H27A120.4
H8A—C8—H8B108.5C26—C27—H27A120.4
C10—C9—C14119.3 (6)C27—C28—C23123.2 (5)
C10—C9—Cl1124.4 (5)C27—C28—H28A118.4
C14—C9—Cl1116.3 (5)C23—C28—H28A118.4
C9—C10—C11121.6 (6)
C15—N1—N2—C163.0 (5)C16—C17—C18—C19179.8 (4)
C21—N3—N4—C221.1 (6)S—C17—C18—C19−0.4 (5)
C1—C2—C3—C4−172.2 (5)C4—O2—C19—C18−63.3 (6)
C19—O2—C4—C3−82.5 (6)C4—O2—C19—C20119.5 (5)
C2—C3—C4—O2−171.2 (5)O1—C18—C19—O23.8 (8)
C5—C6—C7—C8178.2 (5)C17—C18—C19—O2−176.0 (4)
C18—O1—C8—C7−152.1 (4)O1—C18—C19—C20−178.7 (4)
C6—C7—C8—O1−51.8 (7)C17—C18—C19—C201.5 (5)
C14—C9—C10—C114.3 (8)O2—C19—C20—C210.1 (8)
Cl1—C9—C10—C11−178.7 (4)C18—C19—C20—C21−177.5 (4)
C9—C10—C11—C12−4.8 (9)O2—C19—C20—S175.7 (3)
C10—C11—C12—C131.9 (7)C18—C19—C20—S−1.9 (5)
C10—C11—C12—C15−179.9 (5)C17—S—C20—C21177.5 (4)
C11—C12—C13—C141.2 (7)C17—S—C20—C191.4 (3)
C15—C12—C13—C14−176.9 (5)N4—N3—C21—O4−0.6 (6)
C12—C13—C14—C9−1.7 (8)N4—N3—C21—C20177.3 (5)
C10—C9—C14—C13−1.1 (8)C19—C20—C21—N3170.1 (5)
Cl1—C9—C14—C13−178.4 (4)S—C20—C21—N3−5.2 (7)
N2—N1—C15—O3−1.7 (5)C19—C20—C21—O4−12.3 (7)
N2—N1—C15—C12176.4 (5)S—C20—C21—O4172.4 (3)
C11—C12—C15—N110.1 (8)N3—C21—O4—C22−0.2 (5)
C13—C12—C15—N1−171.9 (5)C20—C21—O4—C22−178.2 (4)
C11—C12—C15—O3−172.0 (4)N3—N4—C22—O4−1.2 (6)
C13—C12—C15—O36.0 (7)N3—N4—C22—C23179.2 (5)
N1—C15—O3—C16−0.1 (5)C21—O4—C22—N40.9 (5)
C12—C15—O3—C16−178.4 (4)C21—O4—C22—C23−179.5 (4)
N1—N2—C16—O3−3.2 (5)N4—C22—C23—C28174.8 (5)
N1—N2—C16—C17179.4 (4)O4—C22—C23—C28−4.7 (7)
C15—O3—C16—N22.2 (5)N4—C22—C23—C24−1.1 (8)
C15—O3—C16—C17179.7 (4)O4—C22—C23—C24179.4 (4)
N2—C16—C17—C18172.2 (5)C28—C23—C24—C256.4 (7)
O3—C16—C17—C18−5.0 (7)C22—C23—C24—C25−177.5 (5)
N2—C16—C17—S−7.5 (7)C23—C24—C25—C26−5.5 (9)
O3—C16—C17—S175.3 (3)C24—C25—C26—C270.9 (9)
C20—S—C17—C18−0.6 (3)C24—C25—C26—Cl2−175.8 (5)
C20—S—C17—C16179.2 (4)C25—C26—C27—C283.0 (9)
C8—O1—C18—C19−49.3 (6)Cl2—C26—C27—C28179.6 (4)
C8—O1—C18—C17130.5 (5)C26—C27—C28—C23−1.9 (8)
C16—C17—C18—O10.0 (7)C24—C23—C28—C27−3.1 (8)
S—C17—C18—O1179.7 (3)C22—C23—C28—C27−179.0 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O10.972.573.203 (7)123
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O10.972.573.203 (7)123
references
References top

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