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

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ISSN: 2056-9890

N-Phenyl-4-(8-phenyl-4,5-di­hydro-1,2-benzoxazolo[4,5-d]thia­zol-2-yl)piperidine-1-carboxamide

aKey Laboratory of Pesticide & Chemical Biology, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
*Correspondence e-mail: adzhang@mail.ccnu.edu.cn

(Received 28 May 2009; accepted 3 June 2009; online 17 June 2009)

In the title molecule, C26H24N4O2S, the dihedral angle between the isoxazole ring and the adjoining benzene ring is 21.4 (5)°, and between the isoxazole ring and the thia­zole ring is 14.3 (4)°. The piperidine ring is in a chair conformation. In the crystal structure, mol­ecules are linked by inter­molecular N—H⋯O and weak C—H⋯O hydrogen bonds into one-dimensional chains along [001].

Related literature

The title compound is a potential D1 protease inhibitor. D1 protease is a potential herbicidal target, see: Duff et al. (2007[Duff, S. M. G., Chen, Y.-C. S., Fabbri, B. J., Yalamanchili, G., Hamper, B. C., Walker, D. M., Brookfiled, F. A., Boyd, E. A., Ashton, M. R., Yarnold, C. J. & Cajacob, C. A. (2007). Pestic. Biochem. Physiol. 88, 1-3.]). For synthetic details, see: Bond et al. (2003[Bond, J. W., Hachisu, Y., Matsuura, T. & Suzuk, K. (2003). Org. Lett. 5, 319-394.]); Hu et al. (2009[Hu, D.-J., Liu, S.-F., Huang, T.-H., Tu, H.-Y. & Zhang, A.-D. (2009). Molecules, 14, 1288-1303.]).

[Scheme 1]

Experimental

Crystal data
  • C26H24N4O2S

  • Mr = 456.55

  • Monoclinic, P 21 /c

  • a = 22.2844 (6) Å

  • b = 10.1911 (3) Å

  • c = 10.2842 (3) Å

  • β = 102.282 (2)°

  • V = 2282.11 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.17 mm−1

  • T = 298 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.966, Tmax = 0.983

  • 16337 measured reflections

  • 4477 independent reflections

  • 3399 reflections with I > 2σ(I)

  • Rint = 0.093

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.143

  • S = 1.04

  • 4477 reflections

  • 301 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C17—H17A⋯O2i 0.97 2.40 3.353 (3) 167
N4—H4A⋯O2i 0.854 (10) 2.145 (12) 2.976 (2) 164 (2)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

We are interested in the title compound as a potential D1 protease inhibitor. D1 protease is a potential herbicidal target (Duff et al. 2007). To find the possible D1 inhibitors, virtual screening was performed and a molecule containing isoxazole, thiazole and piperidine rings was designed and synthesized (Hu et al. 2009).

The title moleclue (Fig. 1) contains isoxazole, thiazole, piperdine and two benzene rings. The dihedral angle between the the isoxazole ring and the adjoining benzene ring is 21.4 (5)° and the dihedral angle between the isoxazole and the thiazole rings is 14.3 (4)°. The piperidine ring is in a chair conformation. In the crystal structure, molecules are linked by intermolecular N-H···O and weak C-H···O hydrogen bonds into one-dimensional chains along [001] (see Fig. 2).

Related literature top

The title compound is a potential D1 protease inhibitor. D1 protease is a potential herbicidal target, see: Duff et al. (2007). For synthetic details, see: Bond et al. (2003); Hu et al. (2009).

Experimental top

3-phenyl-6,7-dihydrobenzo[d]isoxazole-4(5H)-one was synthesized by a literature method (Bond et al., 2003). This intermediate (1 mmol) was treated with NBS (2.5 mmol) and NH4OAc (0.1 mmol) in dry ether to obtain the monobromo ketone and a trace amounts of polybromonated derivatives. The target product was formed by a published procedure (Hu et al., 2009). Slow diffusion of hexane into a ethyl acetate solution of the title compound gave single crystals suitable for X-ray analysis.

Refinement top

All H atoms bonded to C atoms were placed in geometrically idealized positions and included in a riding-model approximation with C—H = 0.93 Å (aromatic), 0.97Å (methylene) and 0.98Å (methine), with Uiso(H) = 1.2Ueq(C). The H atom bonded to N4 was found in a difference Fourier map and refined with the restraint of N—H = 0.86 (2)Å and Uiso(H) = 1.2Ueq(N).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 10% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of the title compound with hydrogen bonds drawn as dashed lines. Only H atom involved in hydrogen bonds have been shown.
N-Phenyl-4-(8-phenyl-4,5-dihydro-1,2-benzoxazolo[4,5-d]thiazol- 2-yl)piperidine-1-carboxamide top
Crystal data top
C26H24N4O2SF(000) = 960
Mr = 456.55Dx = 1.329 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4151 reflections
a = 22.2844 (6) Åθ = 2.4–24.8°
b = 10.1911 (3) ŵ = 0.17 mm1
c = 10.2842 (3) ÅT = 298 K
β = 102.282 (2)°Block, colorless
V = 2282.11 (11) Å30.20 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
4477 independent reflections
Radiation source: fine-focus sealed tube3399 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.093
ϕ and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2227
Tmin = 0.966, Tmax = 0.983k = 1212
16337 measured reflectionsl = 1212
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0715P)2 + 0.1065P]
where P = (Fo2 + 2Fc2)/3
4477 reflections(Δ/σ)max = 0.001
301 parametersΔρmax = 0.24 e Å3
1 restraintΔρmin = 0.32 e Å3
Crystal data top
C26H24N4O2SV = 2282.11 (11) Å3
Mr = 456.55Z = 4
Monoclinic, P21/cMo Kα radiation
a = 22.2844 (6) ŵ = 0.17 mm1
b = 10.1911 (3) ÅT = 298 K
c = 10.2842 (3) Å0.20 × 0.10 × 0.10 mm
β = 102.282 (2)°
Data collection top
Bruker SMART CCD
diffractometer
4477 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3399 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.983Rint = 0.093
16337 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0591 restraint
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.24 e Å3
4477 reflectionsΔρmin = 0.32 e Å3
301 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
C10.38381 (9)0.2002 (2)0.3431 (2)0.0421 (5)
C20.34151 (12)0.2361 (2)0.4168 (3)0.0602 (7)
H20.32870.17500.47230.072*
C30.31805 (13)0.3619 (3)0.4091 (3)0.0733 (8)
H30.28940.38460.45920.088*
C40.33650 (12)0.4538 (2)0.3283 (3)0.0663 (7)
H40.32030.53820.32270.080*
C50.37882 (15)0.4196 (3)0.2565 (3)0.0717 (8)
H50.39200.48190.20270.086*
C60.40231 (12)0.2945 (2)0.2623 (2)0.0605 (7)
H60.43090.27280.21170.073*
C70.41255 (9)0.0693 (2)0.35423 (19)0.0398 (5)
C80.39483 (9)0.05256 (19)0.40386 (19)0.0384 (5)
C90.44192 (9)0.1341 (2)0.4002 (2)0.0424 (5)
C100.44851 (11)0.2734 (2)0.4429 (2)0.0520 (6)
H10A0.43260.33030.36790.062*
H10B0.49150.29410.47590.062*
C110.41283 (11)0.2956 (2)0.5528 (2)0.0528 (6)
H11A0.43760.26710.63740.063*
H11B0.40460.38850.55950.063*
C120.35307 (10)0.2212 (2)0.5246 (2)0.0453 (5)
C130.34382 (9)0.10585 (19)0.45761 (19)0.0388 (5)
C140.25309 (10)0.1164 (2)0.5099 (2)0.0449 (5)
C150.18845 (10)0.0794 (2)0.5137 (2)0.0475 (5)
H150.18600.01660.51040.057*
C160.14331 (10)0.1320 (2)0.3913 (2)0.0491 (6)
H16A0.14630.22690.38930.059*
H16B0.15430.09790.31140.059*
C170.07811 (10)0.0935 (3)0.3925 (2)0.0556 (6)
H17A0.05050.13170.31610.067*
H17B0.07400.00120.38630.067*
C180.10164 (10)0.0865 (3)0.6342 (2)0.0595 (7)
H18A0.09780.00830.63470.071*
H18B0.08910.12040.71250.071*
C190.16795 (10)0.1235 (3)0.6394 (2)0.0553 (6)
H19A0.19400.08300.71650.066*
H19B0.17250.21790.64870.066*
C200.01279 (9)0.2148 (2)0.5258 (2)0.0433 (5)
C210.07915 (10)0.3251 (2)0.4003 (2)0.0431 (5)
C220.12464 (11)0.2917 (2)0.2914 (2)0.0561 (6)
H220.11580.23430.22770.067*
C230.18266 (12)0.3426 (3)0.2767 (3)0.0740 (8)
H230.21280.31890.20310.089*
C240.19687 (15)0.4266 (3)0.3673 (4)0.0837 (10)
H240.23660.45870.35770.100*
C250.15178 (17)0.4637 (3)0.4735 (3)0.0849 (10)
H250.16100.52280.53530.102*
C260.09237 (13)0.4143 (3)0.4903 (2)0.0650 (7)
H260.06190.44140.56170.078*
N10.46608 (8)0.05766 (18)0.32118 (18)0.0496 (5)
N20.28756 (7)0.04708 (17)0.44870 (17)0.0424 (4)
N30.06154 (8)0.1393 (2)0.51501 (17)0.0559 (5)
N40.02020 (9)0.2682 (2)0.41087 (17)0.0505 (5)
H4A0.0118 (11)0.252 (2)0.3352 (14)0.061*
O10.48560 (7)0.07301 (15)0.35047 (15)0.0512 (4)
O20.00073 (7)0.23519 (17)0.63341 (15)0.0570 (5)
S10.28825 (3)0.25928 (6)0.58254 (6)0.0556 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0326 (11)0.0463 (12)0.0465 (12)0.0101 (9)0.0064 (9)0.0035 (9)
C20.0577 (15)0.0463 (14)0.0844 (18)0.0019 (11)0.0329 (14)0.0132 (12)
C30.0666 (18)0.0546 (16)0.107 (2)0.0024 (13)0.0374 (16)0.0010 (15)
C40.0605 (17)0.0456 (14)0.0858 (19)0.0021 (12)0.0000 (15)0.0082 (13)
C50.092 (2)0.0520 (16)0.0706 (18)0.0115 (14)0.0173 (16)0.0169 (13)
C60.0689 (17)0.0553 (15)0.0634 (15)0.0096 (13)0.0281 (13)0.0095 (12)
C70.0318 (11)0.0474 (12)0.0407 (11)0.0080 (9)0.0086 (9)0.0010 (9)
C80.0329 (11)0.0428 (11)0.0398 (11)0.0057 (9)0.0088 (9)0.0019 (9)
C90.0374 (12)0.0468 (12)0.0440 (12)0.0053 (10)0.0113 (9)0.0051 (9)
C100.0477 (14)0.0475 (13)0.0621 (14)0.0023 (10)0.0145 (11)0.0070 (11)
C110.0540 (14)0.0445 (12)0.0585 (14)0.0030 (11)0.0088 (11)0.0057 (10)
C120.0455 (13)0.0439 (12)0.0486 (12)0.0052 (10)0.0144 (10)0.0007 (10)
C130.0333 (11)0.0432 (11)0.0400 (11)0.0062 (9)0.0082 (9)0.0002 (9)
C140.0421 (12)0.0473 (12)0.0479 (12)0.0091 (10)0.0154 (10)0.0005 (10)
C150.0400 (12)0.0503 (13)0.0560 (14)0.0094 (10)0.0192 (10)0.0031 (10)
C160.0498 (13)0.0598 (14)0.0421 (12)0.0112 (11)0.0199 (10)0.0044 (10)
C170.0438 (13)0.0783 (17)0.0466 (13)0.0153 (12)0.0141 (10)0.0049 (12)
C180.0449 (14)0.0878 (19)0.0496 (14)0.0157 (12)0.0185 (11)0.0167 (12)
C190.0448 (13)0.0787 (17)0.0440 (13)0.0149 (12)0.0135 (10)0.0100 (11)
C200.0312 (11)0.0647 (14)0.0365 (11)0.0034 (10)0.0129 (9)0.0008 (10)
C210.0422 (12)0.0505 (13)0.0413 (12)0.0065 (10)0.0194 (10)0.0049 (9)
C220.0505 (14)0.0544 (14)0.0616 (15)0.0082 (11)0.0077 (12)0.0006 (11)
C230.0472 (16)0.0771 (19)0.093 (2)0.0052 (14)0.0049 (14)0.0210 (17)
C240.0659 (19)0.106 (2)0.090 (2)0.0389 (18)0.0401 (18)0.040 (2)
C250.111 (3)0.084 (2)0.073 (2)0.0495 (19)0.051 (2)0.0113 (16)
C260.0785 (19)0.0678 (16)0.0510 (15)0.0202 (14)0.0193 (13)0.0004 (12)
N10.0399 (11)0.0538 (12)0.0583 (12)0.0072 (8)0.0179 (9)0.0006 (9)
N20.0348 (10)0.0452 (10)0.0495 (10)0.0071 (8)0.0137 (8)0.0033 (8)
N30.0403 (11)0.0930 (15)0.0373 (10)0.0200 (10)0.0149 (8)0.0040 (10)
N40.0423 (11)0.0793 (14)0.0336 (10)0.0132 (9)0.0160 (8)0.0005 (9)
O10.0378 (8)0.0556 (10)0.0638 (10)0.0034 (7)0.0193 (7)0.0046 (7)
O20.0468 (9)0.0918 (13)0.0377 (8)0.0095 (8)0.0210 (7)0.0037 (8)
S10.0570 (4)0.0477 (4)0.0684 (4)0.0070 (3)0.0272 (3)0.0110 (3)
Geometric parameters (Å, º) top
C1—C21.379 (3)C15—C161.531 (3)
C1—C61.389 (3)C15—H150.9800
C1—C71.474 (3)C16—C171.508 (3)
C2—C31.380 (3)C16—H16A0.9700
C2—H20.9300C16—H16B0.9700
C3—C41.371 (4)C17—N31.463 (3)
C3—H30.9300C17—H17A0.9700
C4—C51.361 (4)C17—H17B0.9700
C4—H40.9300C18—N31.458 (3)
C5—C61.375 (4)C18—C191.515 (3)
C5—H50.9300C18—H18A0.9700
C6—H60.9300C18—H18B0.9700
C7—N11.313 (2)C19—H19A0.9700
C7—C81.430 (3)C19—H19B0.9700
C8—C91.346 (3)C20—O21.225 (2)
C8—C131.470 (3)C20—N31.355 (3)
C9—O11.345 (2)C20—N41.365 (3)
C9—C101.484 (3)C21—C261.373 (3)
C10—C111.531 (3)C21—C221.384 (3)
C10—H10A0.9700C21—N41.419 (3)
C10—H10B0.9700C22—C231.371 (4)
C11—C121.506 (3)C22—H220.9300
C11—H11A0.9700C23—C241.352 (4)
C11—H11B0.9700C23—H230.9300
C12—C131.356 (3)C24—C251.370 (5)
C12—S11.720 (2)C24—H240.9300
C13—N21.375 (3)C25—C261.393 (4)
C14—N21.301 (3)C25—H250.9300
C14—C151.498 (3)C26—H260.9300
C14—S11.744 (2)N1—O11.413 (2)
C15—C191.527 (3)N4—H4A0.854 (10)
C2—C1—C6118.0 (2)C17—C16—H16A109.3
C2—C1—C7122.26 (19)C15—C16—H16A109.3
C6—C1—C7119.6 (2)C17—C16—H16B109.3
C1—C2—C3120.6 (2)C15—C16—H16B109.3
C1—C2—H2119.7H16A—C16—H16B108.0
C3—C2—H2119.7N3—C17—C16110.11 (19)
C4—C3—C2120.7 (3)N3—C17—H17A109.6
C4—C3—H3119.7C16—C17—H17A109.6
C2—C3—H3119.7N3—C17—H17B109.6
C5—C4—C3119.1 (2)C16—C17—H17B109.6
C5—C4—H4120.5H17A—C17—H17B108.2
C3—C4—H4120.5N3—C18—C19110.86 (19)
C4—C5—C6121.0 (2)N3—C18—H18A109.5
C4—C5—H5119.5C19—C18—H18A109.5
C6—C5—H5119.5N3—C18—H18B109.5
C5—C6—C1120.6 (3)C19—C18—H18B109.5
C5—C6—H6119.7H18A—C18—H18B108.1
C1—C6—H6119.7C18—C19—C15111.3 (2)
N1—C7—C8110.43 (19)C18—C19—H19A109.4
N1—C7—C1117.71 (18)C15—C19—H19A109.4
C8—C7—C1131.73 (19)C18—C19—H19B109.4
C9—C8—C7104.49 (18)C15—C19—H19B109.4
C9—C8—C13116.91 (19)H19A—C19—H19B108.0
C7—C8—C13138.57 (19)O2—C20—N3121.71 (19)
O1—C9—C8110.89 (18)O2—C20—N4121.6 (2)
O1—C9—C10121.44 (18)N3—C20—N4116.71 (18)
C8—C9—C10127.67 (19)C26—C21—C22118.9 (2)
C9—C10—C11109.03 (18)C26—C21—N4123.1 (2)
C9—C10—H10A109.9C22—C21—N4117.95 (19)
C11—C10—H10A109.9C23—C22—C21120.5 (3)
C9—C10—H10B109.9C23—C22—H22119.7
C11—C10—H10B109.9C21—C22—H22119.7
H10A—C10—H10B108.3C24—C23—C22121.1 (3)
C12—C11—C10111.11 (18)C24—C23—H23119.4
C12—C11—H11A109.4C22—C23—H23119.4
C10—C11—H11A109.4C23—C24—C25119.0 (3)
C12—C11—H11B109.4C23—C24—H24120.5
C10—C11—H11B109.4C25—C24—H24120.5
H11A—C11—H11B108.0C24—C25—C26121.0 (3)
C13—C12—C11124.5 (2)C24—C25—H25119.5
C13—C12—S1108.90 (17)C26—C25—H25119.5
C11—C12—S1126.36 (16)C21—C26—C25119.4 (3)
C12—C13—N2116.70 (18)C21—C26—H26120.3
C12—C13—C8117.74 (19)C25—C26—H26120.3
N2—C13—C8125.54 (18)C7—N1—O1106.56 (16)
N2—C14—C15123.1 (2)C14—N2—C13110.80 (18)
N2—C14—S1113.77 (16)C20—N3—C18119.97 (18)
C15—C14—S1123.14 (16)C20—N3—C17127.24 (18)
C14—C15—C19114.20 (19)C18—N3—C17112.65 (18)
C14—C15—C16110.96 (18)C20—N4—C21123.28 (18)
C19—C15—C16109.26 (17)C20—N4—H4A122.1 (17)
C14—C15—H15107.4C21—N4—H4A112.7 (17)
C19—C15—H15107.4C9—O1—N1107.61 (15)
C16—C15—H15107.4C12—S1—C1489.84 (10)
C17—C16—C15111.60 (19)
C6—C1—C2—C30.6 (4)C19—C15—C16—C1754.2 (3)
C7—C1—C2—C3176.5 (2)C15—C16—C17—N356.6 (3)
C1—C2—C3—C40.2 (4)N3—C18—C19—C1555.6 (3)
C2—C3—C4—C50.6 (4)C14—C15—C19—C18178.19 (19)
C3—C4—C5—C61.1 (4)C16—C15—C19—C1853.3 (3)
C4—C5—C6—C10.7 (4)C26—C21—C22—C232.8 (4)
C2—C1—C6—C50.1 (4)N4—C21—C22—C23179.3 (2)
C7—C1—C6—C5176.1 (2)C21—C22—C23—C240.3 (4)
C2—C1—C7—N1155.8 (2)C22—C23—C24—C251.8 (4)
C6—C1—C7—N120.0 (3)C23—C24—C25—C261.3 (5)
C2—C1—C7—C819.6 (3)C22—C21—C26—C253.2 (4)
C6—C1—C7—C8164.5 (2)N4—C21—C26—C25179.0 (2)
N1—C7—C8—C91.3 (2)C24—C25—C26—C211.2 (4)
C1—C7—C8—C9174.4 (2)C8—C7—N1—O10.9 (2)
N1—C7—C8—C13178.7 (2)C1—C7—N1—O1175.46 (16)
C1—C7—C8—C133.1 (4)C15—C14—N2—C13178.04 (19)
C7—C8—C9—O11.2 (2)S1—C14—N2—C130.0 (2)
C13—C8—C9—O1179.31 (16)C12—C13—N2—C140.5 (3)
C7—C8—C9—C10178.8 (2)C8—C13—N2—C14177.82 (19)
C13—C8—C9—C100.7 (3)O2—C20—N3—C183.7 (3)
O1—C9—C10—C11151.80 (19)N4—C20—N3—C18175.6 (2)
C8—C9—C10—C1128.2 (3)O2—C20—N3—C17171.6 (2)
C9—C10—C11—C1239.1 (2)N4—C20—N3—C179.1 (4)
C10—C11—C12—C1330.6 (3)C19—C18—N3—C20125.6 (2)
C10—C11—C12—S1155.19 (17)C19—C18—N3—C1758.5 (3)
C11—C12—C13—N2175.8 (2)C16—C17—N3—C20125.6 (2)
S1—C12—C13—N20.7 (2)C16—C17—N3—C1858.8 (3)
C11—C12—C13—C82.7 (3)O2—C20—N4—C2114.7 (3)
S1—C12—C13—C8177.74 (15)N3—C20—N4—C21166.0 (2)
C9—C8—C13—C1213.7 (3)C26—C21—N4—C2048.3 (3)
C7—C8—C13—C12163.5 (2)C22—C21—N4—C20133.9 (2)
C9—C8—C13—N2168.03 (19)C8—C9—O1—N10.7 (2)
C7—C8—C13—N214.8 (4)C10—C9—O1—N1179.28 (18)
N2—C14—C15—C19149.7 (2)C7—N1—O1—C90.1 (2)
S1—C14—C15—C1932.5 (3)C13—C12—S1—C140.54 (16)
N2—C14—C15—C1686.3 (3)C11—C12—S1—C14175.5 (2)
S1—C14—C15—C1691.5 (2)N2—C14—S1—C120.30 (17)
C14—C15—C16—C17179.03 (18)C15—C14—S1—C12177.70 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17A···O2i0.972.403.353 (3)167
N4—H4A···O2i0.85 (1)2.15 (1)2.976 (2)164 (2)
Symmetry code: (i) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC26H24N4O2S
Mr456.55
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)22.2844 (6), 10.1911 (3), 10.2842 (3)
β (°) 102.282 (2)
V3)2282.11 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.17
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.966, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
16337, 4477, 3399
Rint0.093
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.143, 1.04
No. of reflections4477
No. of parameters301
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.32

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17A···O2i0.972.403.353 (3)167.0
N4—H4A···O2i0.854 (10)2.145 (12)2.976 (2)164 (2)
Symmetry code: (i) x, y+1/2, z1/2.
 

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of China (grant Nos. 20672043, 20672044).

References

First citationBond, J. W., Hachisu, Y., Matsuura, T. & Suzuk, K. (2003). Org. Lett. 5, 319–394.  Google Scholar
First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDuff, S. M. G., Chen, Y.-C. S., Fabbri, B. J., Yalamanchili, G., Hamper, B. C., Walker, D. M., Brookfiled, F. A., Boyd, E. A., Ashton, M. R., Yarnold, C. J. & Cajacob, C. A. (2007). Pestic. Biochem. Physiol. 88, 1–3.  Web of Science CrossRef CAS Google Scholar
First citationHu, D.-J., Liu, S.-F., Huang, T.-H., Tu, H.-Y. & Zhang, A.-D. (2009). Molecules, 14, 1288–1303.  Web of Science CSD 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 citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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