organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

7-Chloro-4-(2,5-di­chloro­phen­yl)-1-phenyl-1H-thio­chromeno[2,3-b]pyridine-2,5(3H,4H)-dione

aCollege of Chemistry and Molecular Engineering, Qingdao University of, Science and Technology, Qingdao 266042, People's Republic of China
*Correspondence e-mail: wenlirong@qust.edu.cn

(Received 21 November 2007; accepted 7 January 2008; online 5 March 2008)

In the crystal structure of the title compound, C24H14Cl3NO2S, the tetra­hydro­pyridine ring adopts a half-chair conformation and both pendant benzene rings are oriented nearly perpendicular to the thio­chromeno[2,3-b]pyridine system.

Related literature

For related literature, see: Ingall et al. (1996[Ingall, A. H. (1996). In Comprehensive Heterocyclic Chemistry II, Vol. 5, p 501. Oxford: Pergamon.]), Wang et al. (2006[Wang, W., Li, H., Wang, J. & Zu, L. S. (2006). J. Am. Chem. Soc. 128, 10354-10355.]); Quaglia et al. (2002[Quaglia, W., Pigini, M., Piergentili, A., Giannella, M., Leonardi, A. & Melchiorre, C. (2002). J. Med. Chem. 45, 1633-1643.]).

[Scheme 1]

Experimental

Crystal data
  • C24H14Cl3NO2S

  • Mr = 486.77

  • Monoclinic, P 21 /c

  • a = 13.624 (5) Å

  • b = 13.474 (5) Å

  • c = 11.861 (4) Å

  • β = 95.042 (6)°

  • V = 2168.9 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.54 mm−1

  • T = 294 (2) K

  • 0.18 × 0.12 × 0.10 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.909, Tmax = 0.948

  • 12228 measured reflections

  • 4426 independent reflections

  • 2650 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.112

  • S = 0.99

  • 4426 reflections

  • 280 parameters

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SAINT (Bruker, 1999[Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

N, S-containing heterocycles shows a wide range of biological activities Ingall et al.,1996). For example, the thiochromones (Wang et al.,2006) as important structural motifs exhibit interesting biological properties and have been tested and applied as drugs (Quaglia et al., 2002). In a continuation of our study of structure-activity, we report here the crystal structure of the title compound,(I), which was synthesized from 3-(2,5- dichlorophenyl)-3-oxo-N-phenylpropanethioamide.

The thiopyran ring is almost planar and the 4H-pyridine ring adpots a half-chair conformation. Both benzene rings are oriented nearly perpendicular to the to the thiochromeno[2,3-b]pyridine ring. The bond length C11—O2(1.21 Å) is shorter than C7—O1(1.24 Å), which might be due to the strong electron withdrawing effect of the nitrogen atom in the pyridine ring.

The interest in the N, S-containing heterocycles has been significantly surged since a wide range of biological activities have been identified (Ingall et al.,1996). For example, the thiochromones (Wang et al.,2006) as important structural motifs exhibit interesting biological properties and have been tested and applied as drugs (Quaglia et al., 2002). In a continuation of our study of structure-activity, we report here the crystal structure of the title compound.

Related literature top

For related literature, see: Ingall et al. (1996), Wang et al. (2006); Quaglia et al. (2002).

Experimental top

3-(2,5-dichlorophenyl)-3-oxo-N-phenylpropanethioamide (1 mmol), 2,5-dichlorobenzaldehyde (1 mmol), (2,2-dimethyl-1,3-dioxane-4,6-dione) (1 mmol) and triethylamine (0.5 mmol)were refluxed in anhydrous alcohol for 8 h. The precipitate was filtered off and dissolved in THF. On slow evaporation of the solvent crystals of the title compound has formed (m.p.498 K).

Refinement top

All H atoms were placed in calculated positions, with C—H = 0.93, 0.97 or 0.98 A%, and refined using a riding model with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1999); 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. Crystal structure of the title compound (I) with labeling and displacement ellipsoids drawn at the 50% probability level.
7-Chloro-4-(2,5-dichlorophenyl)-1-phenyl-1H- thiochromeno[2,3-b]pyridine-2,5(3H,4H)-dione top
Crystal data top
C24H14Cl3NO2SF(000) = 992
Mr = 486.77Dx = 1.491 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2857 reflections
a = 13.624 (5) Åθ = 2.3–23.4°
b = 13.474 (5) ŵ = 0.54 mm1
c = 11.861 (4) ÅT = 294 K
β = 95.042 (6)°Prism, yellow
V = 2168.9 (14) Å30.18 × 0.12 × 0.10 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
4426 independent reflections
Radiation source: fine-focus sealed tube2650 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ϕ and ω scansθmax = 26.5°, θmin = 1050°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1617
Tmin = 0.909, Tmax = 0.948k = 1316
12228 measured reflectionsl = 1414
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043 w = 1/[σ2(Fo2) + (0.0479P)2 + 0.2323P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.112(Δ/σ)max = 0.001
S = 0.99Δρmax = 0.28 e Å3
4426 reflectionsΔρmin = 0.26 e Å3
280 parameters
Crystal data top
C24H14Cl3NO2SV = 2168.9 (14) Å3
Mr = 486.77Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.624 (5) ŵ = 0.54 mm1
b = 13.474 (5) ÅT = 294 K
c = 11.861 (4) Å0.18 × 0.12 × 0.10 mm
β = 95.042 (6)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
4426 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2650 reflections with I > 2σ(I)
Tmin = 0.909, Tmax = 0.948Rint = 0.049
12228 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 0.99Δρmax = 0.28 e Å3
4426 reflectionsΔρmin = 0.26 e Å3
280 parameters
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
S10.90221 (5)0.18709 (5)0.44648 (6)0.04544 (19)
Cl11.15911 (7)0.38600 (6)0.09743 (8)0.0852 (3)
Cl20.73863 (7)0.67908 (6)0.56211 (8)0.0848 (3)
Cl30.48232 (6)0.37484 (7)0.27266 (7)0.0859 (3)
O10.92297 (13)0.51190 (12)0.38778 (15)0.0534 (5)
O20.66915 (15)0.28572 (14)0.71540 (16)0.0633 (6)
N10.76934 (14)0.25141 (14)0.57736 (16)0.0395 (5)
C10.97544 (16)0.24922 (17)0.3549 (2)0.0388 (6)
C21.03240 (18)0.18948 (19)0.2898 (2)0.0505 (7)
H21.03270.12110.30040.061*
C31.0880 (2)0.2301 (2)0.2103 (2)0.0581 (8)
H31.12460.18960.16630.070*
C41.08877 (19)0.3324 (2)0.1967 (2)0.0524 (7)
C51.03478 (18)0.39236 (19)0.2611 (2)0.0464 (6)
H51.03660.46080.25110.056*
C60.97697 (16)0.35243 (17)0.3415 (2)0.0370 (6)
C70.91855 (17)0.42134 (18)0.4054 (2)0.0387 (6)
C80.85216 (17)0.38283 (17)0.4844 (2)0.0362 (6)
C90.79469 (17)0.45849 (17)0.5447 (2)0.0408 (6)
H90.83730.51660.55830.049*
C100.77372 (19)0.41789 (18)0.6606 (2)0.0470 (7)
H10A0.83460.41750.70970.056*
H10B0.72810.46210.69400.056*
C110.73121 (19)0.31487 (19)0.6559 (2)0.0450 (6)
C120.83881 (16)0.28430 (17)0.50370 (19)0.0357 (6)
C130.73107 (17)0.15033 (17)0.56871 (19)0.0365 (6)
C140.7620 (2)0.0818 (2)0.6502 (2)0.0540 (7)
H140.80820.09930.70930.065*
C150.7234 (2)0.0139 (2)0.6432 (3)0.0646 (8)
H150.74400.06080.69780.077*
C160.6561 (2)0.0390 (2)0.5570 (3)0.0654 (9)
H160.63010.10290.55280.079*
C170.6263 (2)0.0299 (2)0.4760 (3)0.0656 (9)
H170.58060.01210.41670.079*
C180.6631 (2)0.1252 (2)0.4812 (2)0.0533 (7)
H180.64220.17160.42630.064*
C190.70135 (18)0.49370 (19)0.4760 (2)0.0430 (6)
C200.6704 (2)0.5922 (2)0.4790 (2)0.0545 (7)
C210.5847 (3)0.6240 (2)0.4178 (3)0.0715 (9)
H210.56630.69040.42040.086*
C220.5269 (2)0.5584 (3)0.3538 (3)0.0687 (9)
H220.46920.57960.31320.082*
C230.55580 (19)0.4603 (2)0.3506 (2)0.0548 (7)
C240.64242 (18)0.4289 (2)0.4096 (2)0.0480 (7)
H240.66140.36290.40450.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0490 (4)0.0304 (3)0.0585 (4)0.0002 (3)0.0140 (3)0.0006 (3)
Cl10.0958 (6)0.0721 (6)0.0966 (6)0.0206 (5)0.0581 (5)0.0068 (5)
Cl20.0883 (6)0.0413 (4)0.1249 (8)0.0078 (4)0.0104 (6)0.0151 (5)
Cl30.0627 (5)0.1131 (8)0.0772 (6)0.0090 (5)0.0198 (4)0.0077 (5)
O10.0648 (12)0.0295 (10)0.0678 (12)0.0001 (8)0.0161 (10)0.0042 (9)
O20.0759 (14)0.0576 (13)0.0610 (12)0.0091 (10)0.0315 (11)0.0065 (10)
N10.0441 (12)0.0354 (11)0.0394 (11)0.0040 (10)0.0067 (10)0.0026 (9)
C10.0323 (13)0.0371 (14)0.0466 (15)0.0055 (11)0.0021 (11)0.0025 (12)
C20.0500 (16)0.0335 (14)0.0698 (18)0.0063 (12)0.0161 (14)0.0092 (14)
C30.0531 (17)0.0519 (18)0.073 (2)0.0066 (14)0.0274 (15)0.0147 (15)
C40.0494 (17)0.0490 (17)0.0612 (18)0.0118 (13)0.0181 (14)0.0051 (14)
C50.0436 (15)0.0381 (14)0.0581 (16)0.0082 (12)0.0075 (13)0.0000 (13)
C60.0302 (13)0.0336 (13)0.0465 (14)0.0036 (11)0.0005 (11)0.0006 (12)
C70.0369 (14)0.0339 (14)0.0444 (15)0.0034 (11)0.0022 (12)0.0012 (12)
C80.0353 (13)0.0316 (13)0.0408 (14)0.0005 (11)0.0017 (11)0.0026 (11)
C90.0417 (14)0.0347 (14)0.0457 (15)0.0015 (11)0.0024 (12)0.0029 (12)
C100.0558 (16)0.0411 (15)0.0438 (15)0.0003 (13)0.0022 (13)0.0073 (12)
C110.0522 (16)0.0462 (16)0.0355 (14)0.0019 (13)0.0014 (13)0.0021 (13)
C120.0336 (13)0.0368 (13)0.0360 (13)0.0020 (11)0.0004 (11)0.0014 (11)
C130.0360 (13)0.0373 (13)0.0372 (14)0.0044 (11)0.0083 (11)0.0002 (11)
C140.0525 (17)0.0521 (17)0.0558 (17)0.0012 (14)0.0050 (14)0.0090 (15)
C150.072 (2)0.0414 (17)0.082 (2)0.0038 (15)0.0182 (19)0.0161 (16)
C160.069 (2)0.0457 (18)0.087 (2)0.0152 (16)0.0352 (19)0.0166 (18)
C170.066 (2)0.070 (2)0.061 (2)0.0267 (17)0.0071 (16)0.0144 (18)
C180.0604 (18)0.0563 (18)0.0424 (16)0.0108 (15)0.0004 (14)0.0055 (14)
C190.0424 (15)0.0423 (15)0.0458 (15)0.0057 (12)0.0120 (13)0.0036 (13)
C200.0566 (18)0.0454 (16)0.0632 (18)0.0124 (14)0.0155 (15)0.0031 (14)
C210.079 (2)0.057 (2)0.081 (2)0.0328 (18)0.019 (2)0.0087 (18)
C220.058 (2)0.088 (3)0.061 (2)0.0302 (19)0.0091 (16)0.0115 (19)
C230.0449 (16)0.073 (2)0.0468 (16)0.0085 (15)0.0052 (13)0.0046 (15)
C240.0444 (16)0.0506 (16)0.0495 (16)0.0099 (13)0.0063 (13)0.0027 (14)
Geometric parameters (Å, º) top
S1—C121.739 (2)C9—H90.9800
S1—C11.751 (2)C10—C111.503 (3)
Cl1—C41.739 (3)C10—H10A0.9700
Cl2—C201.744 (3)C10—H10B0.9700
Cl3—C231.737 (3)C13—C181.371 (3)
O1—C71.240 (3)C13—C141.376 (3)
O2—C111.213 (3)C14—C151.393 (4)
N1—C111.398 (3)C14—H140.9300
N1—C121.414 (3)C15—C161.355 (4)
N1—C131.459 (3)C15—H150.9300
C1—C21.397 (3)C16—C171.372 (4)
C1—C61.400 (3)C16—H160.9300
C2—C31.374 (3)C17—C181.377 (4)
C2—H20.9300C17—H170.9300
C3—C41.389 (4)C18—H180.9300
C3—H30.9300C19—C241.384 (3)
C4—C51.370 (3)C19—C201.395 (3)
C5—C61.397 (3)C20—C211.387 (4)
C5—H50.9300C21—C221.368 (4)
C6—C71.475 (3)C21—H210.9300
C7—C81.454 (3)C22—C231.382 (4)
C8—C121.362 (3)C22—H220.9300
C8—C91.504 (3)C23—C241.384 (3)
C9—C191.525 (3)C24—H240.9300
C9—C101.530 (3)
C12—S1—C1102.22 (11)O2—C11—C10124.3 (2)
C11—N1—C12121.9 (2)N1—C11—C10115.2 (2)
C11—N1—C13117.80 (19)C8—C12—N1121.0 (2)
C12—N1—C13120.23 (19)C8—C12—S1126.18 (19)
C2—C1—C6119.7 (2)N1—C12—S1112.79 (16)
C2—C1—S1116.23 (18)C18—C13—C14120.7 (2)
C6—C1—S1124.06 (19)C18—C13—N1119.8 (2)
C3—C2—C1121.1 (2)C14—C13—N1119.4 (2)
C3—C2—H2119.4C13—C14—C15119.2 (3)
C1—C2—H2119.4C13—C14—H14120.4
C2—C3—C4119.0 (3)C15—C14—H14120.4
C2—C3—H3120.5C16—C15—C14120.2 (3)
C4—C3—H3120.5C16—C15—H15119.9
C5—C4—C3120.7 (2)C14—C15—H15119.9
C5—C4—Cl1119.2 (2)C15—C16—C17119.8 (3)
C3—C4—Cl1120.1 (2)C15—C16—H16120.1
C4—C5—C6121.1 (2)C17—C16—H16120.1
C4—C5—H5119.5C16—C17—C18121.1 (3)
C6—C5—H5119.4C16—C17—H17119.5
C5—C6—C1118.3 (2)C18—C17—H17119.5
C5—C6—C7118.1 (2)C13—C18—C17118.9 (3)
C1—C6—C7123.6 (2)C13—C18—H18120.6
O1—C7—C8120.1 (2)C17—C18—H18120.6
O1—C7—C6119.8 (2)C24—C19—C20117.0 (2)
C8—C7—C6120.0 (2)C24—C19—C9121.5 (2)
C12—C8—C7123.8 (2)C20—C19—C9121.5 (2)
C12—C8—C9119.9 (2)C21—C20—C19121.5 (3)
C7—C8—C9116.4 (2)C21—C20—Cl2118.1 (2)
C8—C9—C19113.64 (19)C19—C20—Cl2120.4 (2)
C8—C9—C10109.34 (19)C22—C21—C20120.5 (3)
C19—C9—C10112.3 (2)C22—C21—H21119.8
C8—C9—H9107.1C20—C21—H21119.8
C19—C9—H9107.1C21—C22—C23118.9 (3)
C10—C9—H9107.1C21—C22—H22120.6
C11—C10—C9113.5 (2)C23—C22—H22120.6
C11—C10—H10A108.9C22—C23—C24120.7 (3)
C9—C10—H10A108.9C22—C23—Cl3119.8 (2)
C11—C10—H10B108.9C24—C23—Cl3119.5 (2)
C9—C10—H10B108.9C23—C24—C19121.4 (3)
H10A—C10—H10B107.7C23—C24—H24119.3
O2—C11—N1120.6 (2)C19—C24—H24119.3
C12—S1—C1—C2176.43 (19)C7—C8—C12—S14.3 (3)
C12—S1—C1—C61.4 (2)C9—C8—C12—S1177.11 (17)
C6—C1—C2—C31.8 (4)C11—N1—C12—C817.6 (3)
S1—C1—C2—C3176.1 (2)C13—N1—C12—C8158.9 (2)
C1—C2—C3—C41.3 (4)C11—N1—C12—S1161.51 (17)
C2—C3—C4—C50.2 (4)C13—N1—C12—S122.0 (3)
C2—C3—C4—Cl1179.6 (2)C1—S1—C12—C84.3 (2)
C3—C4—C5—C60.5 (4)C1—S1—C12—N1176.67 (16)
Cl1—C4—C5—C6179.76 (19)C11—N1—C13—C18101.9 (3)
C4—C5—C6—C10.0 (4)C12—N1—C13—C1874.8 (3)
C4—C5—C6—C7178.2 (2)C11—N1—C13—C1476.6 (3)
C2—C1—C6—C51.1 (3)C12—N1—C13—C14106.7 (3)
S1—C1—C6—C5176.60 (18)C18—C13—C14—C150.1 (4)
C2—C1—C6—C7179.3 (2)N1—C13—C14—C15178.4 (2)
S1—C1—C6—C71.5 (3)C13—C14—C15—C160.1 (4)
C5—C6—C7—O11.0 (3)C14—C15—C16—C170.5 (4)
C1—C6—C7—O1179.1 (2)C15—C16—C17—C180.7 (4)
C5—C6—C7—C8175.8 (2)C14—C13—C18—C170.1 (4)
C1—C6—C7—C82.3 (3)N1—C13—C18—C17178.6 (2)
O1—C7—C8—C12176.1 (2)C16—C17—C18—C130.5 (4)
C6—C7—C8—C120.7 (3)C8—C9—C19—C2438.9 (3)
O1—C7—C8—C92.5 (3)C10—C9—C19—C2485.8 (3)
C6—C7—C8—C9179.3 (2)C8—C9—C19—C20142.5 (2)
C12—C8—C9—C1995.5 (3)C10—C9—C19—C2092.8 (3)
C7—C8—C9—C1983.2 (3)C24—C19—C20—C210.3 (4)
C12—C8—C9—C1030.8 (3)C9—C19—C20—C21179.0 (2)
C7—C8—C9—C10150.5 (2)C24—C19—C20—Cl2178.93 (19)
C8—C9—C10—C1149.6 (3)C9—C19—C20—Cl20.3 (3)
C19—C9—C10—C1177.5 (3)C19—C20—C21—C221.1 (4)
C12—N1—C11—O2177.4 (2)Cl2—C20—C21—C22178.2 (2)
C13—N1—C11—O20.8 (3)C20—C21—C22—C230.5 (5)
C12—N1—C11—C103.4 (3)C21—C22—C23—C241.0 (4)
C13—N1—C11—C10180.0 (2)C21—C22—C23—Cl3178.5 (2)
C9—C10—C11—O2143.4 (3)C22—C23—C24—C191.8 (4)
C9—C10—C11—N137.4 (3)Cl3—C23—C24—C19177.65 (19)
C7—C8—C12—N1176.7 (2)C20—C19—C24—C231.1 (4)
C9—C8—C12—N11.9 (3)C9—C19—C24—C23177.5 (2)

Experimental details

Crystal data
Chemical formulaC24H14Cl3NO2S
Mr486.77
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)13.624 (5), 13.474 (5), 11.861 (4)
β (°) 95.042 (6)
V3)2168.9 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.54
Crystal size (mm)0.18 × 0.12 × 0.10
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.909, 0.948
No. of measured, independent and
observed [I > 2σ(I)] reflections
12228, 4426, 2650
Rint0.049
(sin θ/λ)max1)0.627
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.112, 0.99
No. of reflections4426
No. of parameters280
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.26

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
S1—C121.739 (2)C8—C91.504 (3)
S1—C11.751 (2)C9—C101.530 (3)
O2—C111.213 (3)C10—C111.503 (3)
N1—C111.398 (3)
 

Acknowledgements

The authors are very grateful for financial support by the National Natural Science Foundation of China (No. 20572057), the Natural Science Foundation of Shandong Province (No. Y2006B11) and the Doctoral Foundation of Qingdao University of Science and Technology.

References

First citationBruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationIngall, A. H. (1996). In Comprehensive Heterocyclic Chemistry II, Vol. 5, p 501. Oxford: Pergamon.  Google Scholar
First citationQuaglia, W., Pigini, M., Piergentili, A., Giannella, M., Leonardi, A. & Melchiorre, C. (2002). J. Med. Chem. 45, 1633–1643.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, W., Li, H., Wang, J. & Zu, L. S. (2006). J. Am. Chem. Soc. 128, 10354–10355.  Web of Science CSD CrossRef PubMed CAS Google Scholar

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