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Acta Cryst. (2009). E65, o2310    [ doi:10.1107/S1600536809033923 ]

1-Benzyl-3,5-bis(2-thienylmethylene)-4-piperidone

J. Sun and H. Li

Abstract top

In the title compound, C22H19NOS2, the thiophene rings form angles of 69.74 (18) and 65.56 (16)° with the benzene ring. The piperidone ring adopts a half-chair conformation due to the presence of the conjugated ketone systems. Both thiophene rings are disordered over two orientations [occupancies of 0.758 (2)/0.242 (2) and 0.588 (2)/0.412 (2)] at 180° from one another. In the crystal, weak intermolecular C-H...O hydrogen bonds, C-H...[pi] and aromatic [pi]-[pi] stacking interactions [shortest centroid-centroid separation = 3.865 (3) Å] help to stabilize the packing.

Comment top

At present, a series of 3,5-bis(arylidene)-4-piperidone derivatives have been synthesized and proved to display cytotoxic and anticancer properties (El-Subbagh, et al. 2000; Dimmock, et al. 2003). These compounds possess marked affinities for thiols but with little or no affinities for amino or hydroxyl groups found in nucleic acids (Baluja, et al. 1964; Dimmock, et al. 1983). Thus development of these compounds as candidate cytotoxics may lead to the obtention od drugs which lack the undesirable genotoxic properties present in various antineoplastic agents (Benvenuto et al. 1993). Here, we report the title compound (I), which is a combination of cyclic α, β-unsaturated ketone (chalcone) and β-amino ketone, which could be used as a basic unit to prepare antineoplastic compounds.

The molecular structure of the title compound (I) is shown in Fig. 1. The thiophene rings determine angles of 69.74 (18)° and 65.56 (16)° with the benzene ring. The piperidone ring adopts a half-chair conformation due to the presence of conjugated ketone systems,and both of the thiophene rings were found disordered over two orientations, respectively. In the crystal, weak intermolecular C—H···O hydrogen bonds and aromatic π-π stacking interactions [shortest centroid- centroid separation = 3.865 (3) Å] help stabilizing the packing.

Related literature top

For general background, see: Baluja et al. (1964). Benvenuto et al.(1993); Dimmock et al. (1983); Dimmock et al. (2003); El-Subbagh et al. (2000). For details of the synthesis, see: Pati et al. (2009).

Experimental top

The title compound was synthesized according to the literature (Pati et al. 2009). Dry hydrogen chloride was continuously bubbled into a solution of N-benzyl-4-piperidone (0.01 mol) and 2-thieneylaldehyde (0.02 mol) in acetic acid (25 ml) at room temperature. Then the mixture was stirred at room temperature for 8 h., when the precipitate obtained was collected and washed with acetone (20 ml) and added to an aqueous potassium carbonate solution (5%, w/v). The desired product was obtained after the solid was crystallized in a mixture of ethanol and chloroform (1:1, V/V), in a yield of 75.6%. Suitable crystals for X-ray analysis were obtained by slow evaporation of the solution of title compound in a mixture of chloroform and methanol.

Refinement top

All H atoms were positioned geometrically and refined in the riding model approximation with C—H = 0.95 and 0.99 Å. Both thiophene rings were found disordered with occupancies of 0.758 (2)/0.242 (2) and 0.588 (2)/0.412 (2), respectively. The disordered thiophene moieties were restricted to have C—C, Cδbond C and C—S distances of 1.46 (1)Å, 1.36 (1) Å and 1.7 (1) Å, respectively.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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: CrystalStructure (Rigaku/MSC, 2005).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering. Only the main part of each disordered thienyl ring is labelled.
[Figure 2] Fig. 2. The packing diagram of (I). Dashed lines indicate C—H···O hydrogen bonds.
1-Benzyl-3,5-bis(2-thienylmethylene)-4-piperidone top
Crystal data top
C22H19NOS2Z = 2
Mr = 377.50F(000) = 396
Triclinic, P1Dx = 1.361 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.7110 (11) ÅCell parameters from 2974 reflections
b = 9.4072 (19) Åθ = 2.3–27.4°
c = 17.338 (4) ŵ = 0.30 mm−1
α = 87.82 (3)°T = 113 K
β = 87.55 (3)°Block, colorless
γ = 81.99 (3)°0.19 × 0.16 × 0.10 mm
V = 921.1 (3) Å3
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		4321 independent reflections
Radiation source: rotating anode3660 reflections with I > 2σ(I)
confocalRint = 0.031
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.2°
ω and φ scansh = −7→7
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)		k = −11→12
Tmin = 0.945, Tmax = 0.971l = −22→22
9377 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.100 w = 1/[σ2(Fo2) + (0.0449P)2 + 0.2715P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.002
4321 reflectionsΔρmax = 0.33 e Å−3
268 parametersΔρmin = −0.23 e Å−3
58 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.062 (7)
Crystal data top
C22H19NOS2γ = 81.99 (3)°
Mr = 377.50V = 921.1 (3) Å3
Triclinic, P1Z = 2
a = 5.7110 (11) ÅMo Kα radiation
b = 9.4072 (19) ŵ = 0.30 mm−1
c = 17.338 (4) ÅT = 113 K
α = 87.82 (3)°0.19 × 0.16 × 0.10 mm
β = 87.55 (3)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		4321 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)		3660 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 0.971Rint = 0.031
9377 measured reflectionsθmax = 27.9°
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.100Δρmax = 0.33 e Å−3
S = 1.05Δρmin = −0.23 e Å−3
4321 reflectionsAbsolute structure: ?
268 parametersFlack parameter: ?
58 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*/UeqOcc. (<1)
O10.10269 (17)1.04217 (11)0.40042 (6)0.0258 (2)
N10.6906 (2)0.83369 (11)0.29936 (6)0.0179 (2)
S10.62468 (11)1.24588 (7)0.15845 (4)0.02485 (18)0.757 (2)
C10.5420 (7)1.3962 (7)0.1016 (3)0.0266 (8)0.757 (2)
H10.64251.43370.06320.032*0.757 (2)
C20.3140 (7)1.4554 (5)0.1182 (4)0.0254 (7)0.757 (2)
H20.23571.53790.09200.031*0.757 (2)
C30.2069 (10)1.3777 (7)0.1801 (4)0.0271 (8)0.757 (2)
H30.04901.40400.19930.033*0.757 (2)
C40.3533 (11)1.2632 (9)0.2086 (6)0.0188 (9)0.757 (2)
S1'0.1590 (8)1.4029 (5)0.1772 (3)0.0271 (8)0.243 (2)
C1'0.351 (2)1.4701 (19)0.1149 (13)0.0254 (7)0.243 (2)
H1'0.31511.55560.08420.031*0.243 (2)
C2'0.563 (3)1.388 (2)0.1139 (13)0.0266 (8)0.243 (2)
H2'0.69291.40680.08080.032*0.243 (2)
C3'0.5729 (16)1.2660 (11)0.1688 (6)0.02485 (18)0.243 (2)
H3'0.71271.20210.17940.030*0.243 (2)
C4'0.357 (3)1.255 (3)0.2029 (19)0.0188 (9)0.243 (2)
C50.2893 (2)1.17132 (14)0.27215 (8)0.0193 (3)
H50.13371.19680.29350.023*
C60.4133 (2)1.05527 (14)0.30644 (7)0.0178 (3)
C70.3030 (2)0.99300 (14)0.37716 (8)0.0187 (3)
C80.4454 (2)0.87146 (14)0.41855 (7)0.0182 (3)
C90.6814 (2)0.81022 (14)0.38344 (7)0.0190 (3)
H9A0.80740.85580.40610.023*
H9B0.71130.70590.39600.023*
C100.6555 (2)0.98827 (14)0.27952 (8)0.0198 (3)
H10A0.67431.00310.22290.024*
H10B0.77671.03510.30410.024*
C110.3543 (2)0.82590 (14)0.48683 (7)0.0197 (3)
H110.20460.87650.50190.024*
S20.7205 (3)0.61663 (12)0.53477 (8)0.0240 (2)0.5857 (19)
C120.445 (3)0.716 (4)0.5395 (19)0.0203 (8)0.5857 (19)
C130.3181 (9)0.6735 (6)0.6021 (3)0.0232 (3)0.5857 (19)
H130.16060.71550.61450.028*0.5857 (19)
C140.4430 (6)0.5605 (3)0.64780 (19)0.0247 (7)0.5857 (19)
H140.38020.52000.69390.030*0.5857 (19)
C150.6667 (8)0.5177 (7)0.6164 (4)0.0290 (11)0.5857 (19)
H150.77660.44270.63750.035*0.5857 (19)
S2'0.3013 (3)0.64625 (16)0.61623 (9)0.0232 (3)0.4143 (19)
C12'0.469 (4)0.710 (6)0.540 (3)0.0203 (8)0.4143 (19)
C13'0.6958 (16)0.6399 (9)0.5400 (5)0.0240 (2)0.4143 (19)
H13'0.81820.66000.50410.029*0.4143 (19)
C14'0.7256 (14)0.5307 (11)0.6014 (6)0.0290 (11)0.4143 (19)
H14'0.87090.47040.60950.035*0.4143 (19)
C15'0.5303 (10)0.5224 (5)0.6456 (3)0.0247 (7)0.4143 (19)
H15'0.52020.45620.68800.030*0.4143 (19)
C160.9204 (2)0.76582 (15)0.26799 (8)0.0215 (3)
H16A0.94320.66280.28400.026*
H16B1.04790.81100.29000.026*
C170.9401 (2)0.77921 (14)0.18092 (8)0.0196 (3)
C181.1212 (3)0.84215 (15)0.14380 (9)0.0267 (3)
H181.23510.87800.17340.032*
C191.1376 (3)0.85323 (17)0.06335 (9)0.0342 (4)
H191.26260.89620.03830.041*
C200.9723 (3)0.80178 (18)0.02021 (9)0.0355 (4)
H200.98310.8093−0.03460.043*
C210.7906 (3)0.73904 (18)0.05690 (9)0.0329 (4)
H210.67640.70380.02720.039*
C220.7747 (3)0.72757 (16)0.13676 (8)0.0251 (3)
H220.64990.68410.16160.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0185 (5)0.0275 (5)0.0292 (5)0.0011 (4)0.0057 (4)0.0033 (4)
N10.0179 (6)0.0160 (5)0.0182 (5)0.0023 (4)0.0023 (4)0.0001 (4)
S10.0206 (4)0.0249 (3)0.0266 (3)0.0014 (2)0.0062 (2)0.0067 (2)
C10.0339 (12)0.0242 (11)0.021 (2)−0.0028 (9)0.0019 (13)0.0046 (10)
C20.0331 (16)0.0182 (13)0.0241 (10)−0.0003 (12)−0.0031 (13)0.0014 (8)
C30.0295 (19)0.0229 (17)0.0278 (7)0.0002 (12)−0.0064 (11)0.0057 (9)
C40.0208 (7)0.0175 (12)0.0176 (17)−0.0004 (6)−0.0005 (6)−0.0038 (13)
S1'0.0295 (19)0.0229 (17)0.0278 (7)0.0002 (12)−0.0064 (11)0.0057 (9)
C1'0.0331 (16)0.0182 (13)0.0241 (10)−0.0003 (12)−0.0031 (13)0.0014 (8)
C2'0.0339 (12)0.0242 (11)0.021 (2)−0.0028 (9)0.0019 (13)0.0046 (10)
C3'0.0206 (4)0.0249 (3)0.0266 (3)0.0014 (2)0.0062 (2)0.0067 (2)
C4'0.0208 (7)0.0175 (12)0.0176 (17)−0.0004 (6)−0.0005 (6)−0.0038 (13)
C50.0174 (6)0.0186 (6)0.0218 (6)−0.0022 (5)0.0005 (5)−0.0015 (5)
C60.0170 (6)0.0171 (6)0.0194 (6)−0.0029 (5)0.0005 (5)−0.0030 (5)
C70.0178 (6)0.0168 (6)0.0214 (6)−0.0023 (5)0.0001 (5)−0.0029 (5)
C80.0185 (7)0.0174 (6)0.0193 (6)−0.0036 (5)−0.0007 (5)−0.0032 (5)
C90.0182 (6)0.0192 (6)0.0187 (6)−0.0002 (5)−0.0001 (5)0.0006 (5)
C100.0192 (7)0.0173 (6)0.0216 (6)0.0005 (5)0.0025 (5)0.0014 (5)
C110.0202 (7)0.0189 (6)0.0202 (6)−0.0031 (5)0.0001 (5)−0.0030 (5)
S20.0215 (5)0.0240 (5)0.0242 (4)0.0047 (3)−0.0041 (3)0.0019 (3)
C120.025 (3)0.019 (2)0.0171 (7)−0.004 (3)−0.002 (3)−0.0014 (8)
C130.0233 (5)0.0290 (7)0.0169 (7)−0.0053 (4)0.0021 (4)0.0048 (4)
C140.035 (2)0.0210 (17)0.0186 (8)−0.0037 (13)−0.0021 (14)0.0007 (11)
C150.041 (3)0.0247 (15)0.021 (3)0.000 (2)−0.010 (2)0.0045 (12)
S2'0.0233 (5)0.0290 (7)0.0169 (7)−0.0053 (4)0.0021 (4)0.0048 (4)
C12'0.025 (3)0.019 (2)0.0171 (7)−0.004 (3)−0.002 (3)−0.0014 (8)
C13'0.0215 (5)0.0240 (5)0.0242 (4)0.0047 (3)−0.0041 (3)0.0019 (3)
C14'0.041 (3)0.0247 (15)0.021 (3)0.000 (2)−0.010 (2)0.0045 (12)
C15'0.035 (2)0.0210 (17)0.0186 (8)−0.0037 (13)−0.0021 (14)0.0007 (11)
C160.0192 (7)0.0220 (6)0.0215 (7)0.0042 (5)−0.0006 (5)−0.0021 (5)
C170.0187 (7)0.0162 (6)0.0218 (6)0.0047 (5)0.0023 (5)−0.0008 (5)
C180.0243 (7)0.0219 (7)0.0327 (8)−0.0012 (6)0.0043 (6)−0.0001 (6)
C190.0343 (9)0.0281 (8)0.0359 (9)0.0034 (7)0.0152 (7)0.0090 (6)
C200.0445 (10)0.0348 (8)0.0204 (7)0.0153 (7)0.0056 (7)0.0043 (6)
C210.0342 (9)0.0361 (8)0.0257 (7)0.0073 (7)−0.0061 (6)−0.0059 (6)
C220.0225 (7)0.0264 (7)0.0252 (7)0.0002 (6)0.0018 (5)−0.0024 (6)
Geometric parameters (Å, °) top
O1—C71.2301 (17)C11—C121.413 (4)
N1—C91.4659 (16)C11—C12'1.497 (5)
N1—C161.4688 (17)C11—H110.9500
N1—C101.4696 (16)S2—C151.704 (4)
S1—C11.715 (3)S2—C121.716 (6)
S1—C41.735 (3)C12—C131.355 (6)
C1—C21.366 (4)C13—C141.428 (5)
C1—H10.9500C13—H130.9500
C2—C31.439 (6)C14—C151.381 (5)
C2—H20.9500C14—H140.9500
C3—C41.359 (5)C15—H150.9500
C3—H30.9500S2'—C15'1.707 (5)
C4—C51.441 (3)S2'—C12'1.735 (7)
S1'—C1'1.677 (9)C12'—C13'1.372 (8)
S1'—C4'1.720 (9)C13'—C14'1.450 (7)
C1'—C2'1.342 (9)C13'—H13'0.9500
C1'—H1'0.9500C14'—C15'1.336 (6)
C2'—C3'1.458 (8)C14'—H14'0.9500
C2'—H2'0.9500C15'—H15'0.9500
C3'—C4'1.361 (9)C16—C171.5108 (18)
C3'—H3'0.9500C16—H16A0.9900
C4'—C51.479 (9)C16—H16B0.9900
C5—C61.3484 (19)C17—C181.385 (2)
C5—H50.9500C17—C221.390 (2)
C6—C71.4917 (18)C18—C191.395 (2)
C6—C101.5007 (18)C18—H180.9500
C7—C81.4870 (18)C19—C201.378 (3)
C8—C111.3515 (19)C19—H190.9500
C8—C91.5031 (18)C20—C211.384 (3)
C9—H9A0.9900C20—H200.9500
C9—H9B0.9900C21—C221.385 (2)
C10—H10A0.9900C21—H210.9500
C10—H10B0.9900C22—H220.9500
C9—N1—C16109.11 (10)C8—C11—C12130.8 (5)
C9—N1—C10110.22 (10)C8—C11—C12'126.7 (6)
C16—N1—C10110.54 (11)C8—C11—H11114.6
C1—S1—C492.37 (16)C12—C11—H11114.6
C2—C1—S1111.8 (2)C12'—C11—H11118.6
C2—C1—H1124.1C15—S2—C1292.9 (2)
S1—C1—H1124.1C13—C12—C11123.1 (5)
C1—C2—C3111.8 (3)C13—C12—S2110.5 (3)
C1—C2—H2124.1C11—C12—S2126.4 (4)
C3—C2—H2124.1C12—C13—C14114.0 (4)
C4—C3—C2113.5 (4)C12—C13—H13123.0
C4—C3—H3123.3C14—C13—H13123.0
C2—C3—H3123.3C15—C14—C13111.2 (3)
C3—C4—C5123.9 (4)C15—C14—H14124.4
C3—C4—S1110.5 (3)C13—C14—H14124.4
C5—C4—S1125.6 (2)C14—C15—S2111.3 (3)
C1'—S1'—C4'93.9 (4)C14—C15—H15124.3
C2'—C1'—S1'111.4 (5)S2—C15—H15124.3
C2'—C1'—H1'124.3C15'—S2'—C12'93.0 (3)
S1'—C1'—H1'124.3C13'—C12'—C11130.6 (6)
C1'—C2'—C3'112.9 (6)C13'—C12'—S2'110.3 (4)
C1'—C2'—H2'123.5C11—C12'—S2'119.1 (5)
C3'—C2'—H2'123.5C12'—C13'—C14'111.5 (5)
C4'—C3'—C2'111.5 (6)C12'—C13'—H13'124.2
C4'—C3'—H3'124.3C14'—C13'—H13'124.2
C2'—C3'—H3'124.3C15'—C14'—C13'114.0 (5)
C3'—C4'—C5130.6 (14)C15'—C14'—H14'123.0
C3'—C4'—S1'109.9 (6)C13'—C14'—H14'123.0
C5—C4'—S1'116.2 (8)C14'—C15'—S2'111.3 (4)
C6—C5—C4130.75 (18)C14'—C15'—H15'124.4
C6—C5—C4'128.6 (4)S2'—C15'—H15'124.4
C6—C5—H5114.6N1—C16—C17112.48 (11)
C4—C5—H5114.6N1—C16—H16A109.1
C4'—C5—H5116.6C17—C16—H16A109.1
C5—C6—C7117.13 (12)N1—C16—H16B109.1
C5—C6—C10124.42 (12)C17—C16—H16B109.1
C7—C6—C10118.43 (11)H16A—C16—H16B107.8
O1—C7—C8121.69 (12)C18—C17—C22118.98 (13)
O1—C7—C6120.77 (12)C18—C17—C16121.17 (13)
C8—C7—C6117.54 (11)C22—C17—C16119.85 (13)
C11—C8—C7117.02 (12)C17—C18—C19120.50 (15)
C11—C8—C9124.41 (12)C17—C18—H18119.8
C7—C8—C9118.55 (11)C19—C18—H18119.8
N1—C9—C8111.58 (11)C20—C19—C18119.98 (15)
N1—C9—H9A109.3C20—C19—H19120.0
C8—C9—H9A109.3C18—C19—H19120.0
N1—C9—H9B109.3C19—C20—C21119.85 (14)
C8—C9—H9B109.3C19—C20—H20120.1
H9A—C9—H9B108.0C21—C20—H20120.1
N1—C10—C6110.42 (11)C20—C21—C22120.19 (16)
N1—C10—H10A109.6C20—C21—H21119.9
C6—C10—H10A109.6C22—C21—H21119.9
N1—C10—H10B109.6C21—C22—C17120.50 (15)
C6—C10—H10B109.6C21—C22—H22119.7
H10A—C10—H10B108.1C17—C22—H22119.7
C4—S1—C1—C2−1.8 (8)C9—N1—C10—C6−63.56 (14)
S1—C1—C2—C31.4 (9)C16—N1—C10—C6175.74 (11)
C1—C2—C3—C4−0.1 (12)C5—C6—C10—N1−150.83 (13)
C2—C3—C4—C5178.1 (10)C7—C6—C10—N131.04 (16)
C2—C3—C4—S1−1.2 (13)C7—C8—C11—C12−180 (3)
C1—S1—C4—C31.7 (10)C9—C8—C11—C12−1(3)
C1—S1—C4—C5−177.6 (10)C7—C8—C11—C12'−177 (4)
C4'—S1'—C1'—C2'−2(3)C9—C8—C11—C12'1(4)
S1'—C1'—C2'—C3'−2(3)C8—C11—C12—C13−173 (2)
C1'—C2'—C3'—C4'6(4)C8—C11—C12—S27(6)
C2'—C3'—C4'—C5−166 (3)C15—S2—C12—C130(3)
C2'—C3'—C4'—S1'−7(4)C15—S2—C12—C11−179 (4)
C1'—S1'—C4'—C3'5(3)C11—C12—C13—C14−180 (3)
C1'—S1'—C4'—C5167 (3)S2—C12—C13—C140(4)
C3—C4—C5—C6−180.0 (8)C12—C13—C14—C15−1(3)
S1—C4—C5—C6−0.7 (15)C13—C14—C15—S21.3 (7)
C3—C4—C5—C4'117 (16)C12—S2—C15—C14−0.9 (19)
S1—C4—C5—C4'−64 (14)C8—C11—C12'—C13'11 (9)
C3'—C4'—C5—C6−20 (6)C8—C11—C12'—S2'−169 (2)
S1'—C4'—C5—C6−177.4 (12)C15'—S2'—C12'—C13'−2(5)
C3'—C4'—C5—C4100 (18)C15'—S2'—C12'—C11178 (5)
S1'—C4'—C5—C4−57 (12)C11—C12'—C13'—C14'−178 (6)
C4—C5—C6—C7173.6 (8)S2'—C12'—C13'—C14'2(5)
C4'—C5—C6—C7179 (2)C12'—C13'—C14'—C15'−1(4)
C4—C5—C6—C10−4.6 (8)C13'—C14'—C15'—S2'−0.4 (13)
C4'—C5—C6—C101(2)C12'—S2'—C15'—C14'1(3)
C5—C6—C7—O13.41 (19)C9—N1—C16—C17177.35 (11)
C10—C6—C7—O1−178.32 (12)C10—N1—C16—C17−61.29 (15)
C5—C6—C7—C8−175.80 (12)N1—C16—C17—C18123.42 (14)
C10—C6—C7—C82.48 (18)N1—C16—C17—C22−56.69 (16)
O1—C7—C8—C11−6.0 (2)C22—C17—C18—C19−0.1 (2)
C6—C7—C8—C11173.18 (12)C16—C17—C18—C19179.75 (12)
O1—C7—C8—C9175.57 (12)C17—C18—C19—C200.2 (2)
C6—C7—C8—C9−5.24 (18)C18—C19—C20—C21−0.1 (2)
C16—N1—C9—C8−177.33 (11)C19—C20—C21—C22−0.1 (2)
C10—N1—C9—C861.11 (15)C20—C21—C22—C170.2 (2)
C11—C8—C9—N1155.81 (13)C18—C17—C22—C21−0.1 (2)
C7—C8—C9—N1−25.90 (16)C16—C17—C22—C21−179.98 (13)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O1i0.992.593.4946 (18)151
C10—H10B···O1i0.992.563.4747 (18)153
C11—H11···O1ii0.952.453.319 (2)153
C13—H13···O1ii0.952.563.338 (6)140
C2—H2···Cg6iii0.952.683.520 (5)148
Symmetry codes: (i) x+1, y, z; (ii) −x, −y+2, −z+1; (iii) x−1, y+1, z.
Table 1
Selected geometric parameters (Å, °) top
O1—C71.2301 (17)C8—C111.3515 (19)
N1—C161.4688 (17)
C9—N1—C16109.11 (10)C1—S1—C492.37 (16)
C9—N1—C10110.22 (10)C6—C5—C4130.75 (18)
C4—S1—C1—C2−1.8 (8)S1—C4—C5—C6−0.7 (15)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O1i0.992.593.4946 (18)151
C10—H10B···O1i0.992.563.4747 (18)153
C11—H11···O1ii0.952.453.319 (2)153
C13—H13···O1ii0.952.563.338 (6)140
C2—H2···Cg6iii0.952.683.520 (5)148
Symmetry codes: (i) x+1, y, z; (ii) −x, −y+2, −z+1; (iii) x−1, y+1, z.
Acknowledgements top

The authors are grateful to Binzhou Medical college for financial support.

references
References top

Baluja, G., Municio, A. M. & Vega, S. (1964). Chem. Ind. pp. 2053–2054.

Benvenuto, J. A., Connor, T. A., Monteith, D. K., Laidlaw, J. W., Adams, S. C., Matney, T. S. & Theiss, J. C. (1993). J. Pharm. Sci. 82, 988–991.

Dimmock, J. R., Jha, A., Zello, G. A., Sharma, R. K., Shrivastav, A., Selvakumar, P., Allen, T. M., Santos, C. L., Balzarini, J., Clercq, E. D., Manavathu, E. K. & Stables, J. P. (2003). J. Enzyme Inhib. Med. Chem. 18, 325–332.

Dimmock, J. R., Raghavan, S. K., Logan, B. M. & Bigam, G. E. (1983). Eur. J. Med. Chem. 18, 248–254.

El-Subbagh, H. I., Abu-Zaid, S. M., Mahran, M. A., Badria, F. A. & Al-Obaid, A. M. (2000). J. Med. Chem. 43, 2915–2921.

Pati, H. N., Das, U., Das, S. & Bandy, B. (2009). Eur. J. Med. Chem. 44, 54-62.

Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.